A compound is represented by one of formulae (11) to (13). R 1 to R 4 each independently represent a group represented by a formula (1-1) or the like, or a group represented by a formula (2-1), a group represented by a formula (2-2) or the like. At least one of R 1 to R 4 is the group represented by the formula (1-1) or the like. At least one of R 1 to R 4 is the group represented by the formula (2-1), (2-2) or the like. For instance, X 1 represents an oxygen atom, a sulfur atom, or CR 151 R 152 , R 101 to R 110 and R 151 and R 152 each independently representing a hydrogen atom or a substituent. For instance, R 161 to R 168 and R 171 and R 180 each independently represent a hydrogen atom or a substituent. * each independently represents a bonding position to a carbon atom in a benzene ring in each of formulae (11) to (13): [structure]

Description

79 parts

›TECHNICAL FIELD

The present invention relates to a compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device.

›BACKGROUND ART

When a voltage is applied to an organic electroluminescence device (hereinafter, sometimes referred to as an “organic EL device”), holes are injected from an anode and electrons are injected from a cathode into an emitting layer. The injected electrons and holes are recombined in the emitting layer to form excitons. Specifically, according to the electron spin statistics theory, singlet excitons and triplet excitons are generated at a ratio of 25%:75%.

A fluorescent organic EL device using light emission from singlet excitons has been applied to a full-color display such as a mobile phone and a television set, but an internal quantum efficiency is said to be at a limit of 25%. Accordingly, studies has been made to improve a performance of the organic EL device.

Moreover, it is expected to further efficiently emit the organic EL device using triplet excitons in addition to singlet excitons. In view of the above, a highly efficient fluorescent organic EL device using thermally activated delayed fluorescence (hereinafter, sometimes simply referred to as “delayed fluorescence”) has been proposed and studied.

For instance, a TADF (Thermally Activated Delayed Fluorescence) mechanism has been studied. The TADF mechanism uses such a phenomenon that inverse intersystem crossing from triplet excitons to singlet excitons thermally occurs when a material having a small energy difference (ΔST) between singlet energy level and triplet energy level is used. Delayed fluorescence (thermally activated delayed fluorescence) is explained in “Yuki Hando-tai no Debaisu Bussei (Device Physics of Organic Semiconductors)” (edited by ADACHI, Chihaya, published by Kodansha, issued on Apr. 1, 2012, on pages 261-268).

As a compound exhibiting TADF properties (hereinafter also referred to as a TADF compound), for example, a compound in which a donor moiety and an acceptor moiety are bonded in a molecule is known.

For instance, Patent Literatures 1 and 2 disclose a compound in which a fused carbazole group and a cyano group are bonded to a benzene ring.

›CITATION LIST

Patent Literature(s)

Patent Literature 1: International Publication No. WO2014/146752

Patent Literature 2: International Publication No. WO2014/208698

›SUMMARY OF THE INVENTION · 1 of 2

Problems to be Solved by the Invention

In a compound, such as those disclosed in Patent Literatures 1 and 2, in which a plurality of cyano groups having a relatively high acceptor properties and a fused plurality of carbazole groups having a relatively high donor properties are simply bonded to a benzene, a sublimation temperature of the compound tends to be increased when the compound is sublimated and purified. When the sublimation temperature of the compound is increased, a purification time is prolonged to reduce a purification efficiency. In recent years, the sublimation temperature is required to be further decreased in terms of the purification efficiency.

In the meantime, it is crucial that TADF properties of the TADF compound are kept favorable.

An object of the invention is to provide a compound capable of decreasing a sublimation temperature when being sublimated and purified while maintaining TADF properties, an organic-EL-device material containing the compound, an organic EL device containing the compound, and an electronic device provided with the organic EL device.

Another object of the invention is to provide the organic EL device and the electronic device each having an excellent performance by using the compound and the organic-EL-device material containing the compound, to provide a compound capable of achieving the organic EL device and the electronic device each having an excellent performance, and to provide the organic-EL-device material containing the compound.

Means for Solving the Problems

According to an aspect of the invention, a compound represented by one of formulae (11) to (13) below is provided.

In the formulae (11) to (13), R 1 to R 4 are each independently a group represented by one of formulae (1-1) to (1-6) or a group represented by one of formulae (2-1) to (2-4). However, at least one of R 1 to R 4 is the group represented by one of formulae (1-1) to (1-6) while at least one of R 1 to R 4 is the group represented by one of formulae (2-1) to (2-4).

In the formula (1-1): X 1 is an oxygen atom, a sulfur atom, or CR 151 R 152 ; R 101 to R 110 are each independently a hydrogen atom or a substituent; R 151 and R 152 are each independently a hydrogen atom or a substituent, or R 151 and R 152 are mutually bonded to form a ring.

R 101 to R 110 , R 151 and R 152 as the substituent each independently represent a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkysilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms.

In the formula (1-2), X 2 and R 111 to R 120 respectively represent the same as X 1 and R 101 to R 110 in the formula (1-1).

In the formula (1-3), X 3 and R 121 to R 130 respectively represent the same as X 1 and R 101 to R 110 in the formula (1-1).

In the formula (1-4), X 4 and R 131 to R 140 respectively represent the same as X 1 and R 101 to R 110 in the formula (1-1).

In the formula (1-5), X 5 and R 141 to R 150 respectively represent the same as X 1 and R 101 to R 110 in the formula (1-1).

In the formula (1-6), X 6 and R 61 to R 70 respectively represent the same as X 1 and R 101 to R 110 in the formula (1-1). * each independently represents a bonding position to a carbon atom in a benzene ring in each of the formulae (11) to (13).

In the formula (2-1), R 161 to R 168 each independently represent a hydrogen atom or a substituent.

R 161 to R 168 as the substituent each independently represent a halogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms, a substituted or unsubstituted alkysilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms.

In the formula (2-2), R 171 to R 180 each independently represent a hydrogen atom or a substituent. R 171 to R 180 as the substituent each independently represent the same examples of the substituent for R 161 to R 168 in the formula (2-1).

In the formula (2-3), R 181 to R 190 each independently represent a hydrogen atom or a substituent. R 181 to R 190 as the substituent each independently represent the same examples of the substituent for R 161 to R 168 in the formula (2-1).

In the formula (2-4), R 191 to R 200 each independently represent a hydrogen atom or a substituent. R 191 to R 200 as the substituent each independently represent the same examples of the substituent for R 161 to R 168 in the formula (2-1). * each independently represents a bonding position to a carbon atom in a benzene ring in each of the formulae (11) to (13).

According to another aspect of the invention, an organic-electroluminescence-device material containing the compound according to the above aspect of the invention is provided.

According to still another aspect of the invention, an organic electroluminescence device: including an anode; a cathode; and a first organic layer provided between the anode and the cathode, in which the first organic layer contains a first compound, and the first compound is the compound according to the above aspect of the invention is provided.

›SUMMARY OF THE INVENTION · 2 of 2

According to a further aspect of the invention, an electronic device provided with the organic electroluminescence device according to the above aspect of the invention is provided.

According to the above aspects of the invention, a compound capable of decreasing a sublimation temperature when being sublimated and purified while maintaining TADF properties, an organic-EL-device material containing the compound, an organic EL device containing the compound, and an electronic device provided with the organic EL device can be provided.

›BRIEF EXPLANATION OF DRAWING(S)

FIG. 1 is a figure schematically illustrating an arrangement of an organic electroluminescence device according to a third exemplary embodiment of the invention.

FIG. 2 schematically shows a device of measuring transient PL.

FIG. 3 shows an example of a decay curve of the transient PL.

FIG. 4 shows a relationship in energy level and energy transfer between a first compound and a second compound in an emitting layer of an exemplary organic electroluminescence device according to a third exemplary embodiment of the invention.

FIG. 5 shows a relationship in energy level and energy transfer between a first compound, a second compound and a third compound in an emitting layer of an exemplary organic electroluminescence device according to a fourth exemplary embodiment of the invention.

FIG. 6 shows a relationship in energy level and energy transfer between the first compound and a fourth compound in an emitting layer of an exemplary organic electroluminescence device according to a fifth exemplary embodiment of the invention.

›MEANS FOR SOLVING THE PROBLEMS · 1 of 23

First Exemplary Embodiment

Compound

A compound according to a first exemplary embodiment is represented by one of formulae (11) to (13) below.

In the formula (1-1): X 1 is an oxygen atom, a sulfur atom, or CR 151 R 152 : R 101 to R 110 are each independently a hydrogen atom or a substituent; and R 151 and R 152 are each independently a hydrogen atom or a substituent, or R 151 and R 152 are mutually bonded to form a ring.

In the formula (1-2), X 2 and R 111 to R 120 respectively represent the same as X 1 and R 101 to R 110 in the formula (1-1).

In the formula (1-3), X 3 and R 121 to R 130 respectively represent the same as X 1 and R 101 to R 110 in the formula (1-1).

In the formula (1-4), X 4 and R 131 to R 140 respectively represent the same as X 1 and R 101 to R 110 in the formula (1-1).

In the formula (1-5), X 5 and R 141 to R 150 respectively represent the same as X 1 and R 101 to R 110 in the formula (1-1).

In the formulae (1-1) to (1-6), when one or more of R 101 to R 110 , R 111 to R 120 , R 121 to R 130 , R 131 to R 140 , R 141 to R 150 , R 61 to R 70 , R 151 and R 152 are hydrogen atom(s), it is preferable that all of the hydrogen atom(s) are protium, one or more of the hydrogen atom(s) are deuterium, or all of the hydrogen atom(s) are deuterium.

In the formulae (1-1) to (1-6), when one or more of R 101 to R 110 , R 111 to R 120 , R 121 to R 130 , R 131 to R 140 , R 141 to R 150 , R 61 to R 70 , R 151 and R 152 are substituent(s) and the substituent(s) have one or more hydrogen atom(s), it is preferable that all of the hydrogen atom(s) are protium, one or more of the hydrogen atom(s) are deuterium, or all of the hydrogen atom(s) are deuterium.

In the formula (2-1), R 161 to R 168 each independently represent a hydrogen atom or a substituent.

In the formulae (2-1) to (2-4), when one or more of R 161 to R 168 , R 171 to R 180 , R 181 to R 190 and R 191 to R 200 are hydrogen atom(s), it is preferable that all of the hydrogen atom(s) are protium, one or more of the hydrogen atom(s) are deuterium, or all of the hydrogen atom(s) are deuterium.

In the formulae (2-1) to (2-4), when one or more of R 161 to R 168 , R 171 to R 180 , R 181 to R 190 and R 191 to R 200 are substituent(s) and the substituent(s) have one or more hydrogen atom(s), it is preferable that all of the hydrogen atom(s) are protium, one or more of the hydrogen atom(s) are deuterium, or all of the hydrogen atom(s) are deuterium.

A group formed by bonding a five-membered ring (in which a hetero atom is not a nitrogen atom) and a benzene ring to a carbazole group is specifically a group represented by one of formulae (1-1) to (1-6) (hereinafter, also referred to as a “five-ring carbazole group”). It is inferred that a compound formed by bonding the five-ring carbazole group to dicyanobenzene works well for properties of the organic EL device.

It is believed that this is because a conjugation length of the five-ring carbazole group extends longer than that of, for instance, each of groups represented by formulae (2-1) to (2-4). It is also believed that a skeleton specific to the five-ring carbazole group is contributable. For this reason, an ionization potential tends to become low (an absolute value tends to become small). As a result, when the compound having the five-ring carbazole group is contained, for instance, in the emitting layer, it is inferred that hole injection properties from the hole transporting layer to the emitting layer are improved while charge transport properties in the emitting layer are improved.

›MEANS FOR SOLVING THE PROBLEMS · 2 of 23

In contrast, with respect to a compound formed by bonding four five-ring carbazole groups having the above charge transport properties to, for instance, dicyanobenzene, a sublimation temperature is easily increased when the compound is sublimated and purified. When the sublimation temperature of the compound is increased, a purifying time is prolonged to reduce a purification efficiency.

The inventors have found a compound capable of decreasing the sublimation temperature while keeping TADF properties, the compound formed by bonding four groups in total of (i) the five-ring carbazole group (i.e., groups represented by the formulae (1-1) to (1-6)) and (ii) the three-ring or four-ring carbazole group (groups represented by the formulae (2-1) to (2-4)) to dicyanobenzene.

In other words, with respect to the compound of the exemplary embodiment, it is expected that the five-ring carbazole group and the three-ring or four-ring carbazole group contained in a single compound contributes to decrease in the sublimation temperature.

In addition, since the three-ring or four-ring carbazole group has a skeleton having a higher triplet energy than the five-ring carbazole group, it is expected that, for instance, presence of the three-ring or four-ring carbazole group in the emitting layer can express the function of inhibiting energy deactivation from the triplet state.

Thus, according to the exemplary embodiment, it is expected that the combined use of the “five-ring carbazole group” having excellent charge transport properties and the “three-ring or four-ring carbazole group” can keep a balance between the decrease in the sublimation temperature and the maintenance of the TADF properties. As a result, it is expected that the compound capable of decreasing the sublimation temperature when the compound is sublimated and purified, while maintaining the TADF properties, can be obtained.

Maintaining of the TADF properties herein means, for instance, specifically the “value of X D /X P ”, which is measured in Examples, is 0.05 or more.

The amount of Prompt emission is denoted by X P and the amount of Delay emission is denoted by X D . Details of the measurement method is described in the description about Examples.

In the compound of the exemplary embodiment, when a plurality of groups represented by the formula (1-1) are present as groups for R 1 to R 4 , the plurality of groups represented by the formula (1-1) are preferably the same group having the same substituent.

When a plurality of groups represented by the formula (1-2) are present as the groups for R 1 to R 4 , the plurality of groups represented by the formula (1-2) are preferably the same group having the same substituent.

When a plurality of groups represented by the formula (1-3) are present as groups for R 1 to R 4 , the plurality of groups represented by the formula (1-3) are preferably the same group having the same substituent.

When a plurality of groups represented by the formula (1-4) are present as groups for R 1 to R 4 , the plurality of groups represented by the formula (1-4) are preferably the same group having the same substituent.

When a plurality of groups represented by the formula (1-5) are present as groups for R 1 to R 4 , the plurality of groups represented by the formula (1-5) are preferably the same group having the same substituent.

When a plurality of groups represented by the formula (1-6) are present as groups for R 1 to R 4 , the plurality of groups represented by the formula (1-6) are preferably the same group having the same substituent.

Specifically, for instance, when two groups represented by the formula (1-1) are selected as the groups for R 1 and R 2 , one group represented by the formula (1-2) is selected as the group for R 3 , and one group represented by the formula (2-1) is selected as the group for R 4 , the two groups represented by the formula (1-1) are preferably the same group having the same substituent.

Moreover, for instance, when three groups represented by the formula (1-1) are selected as the groups for R 1 to R 3 , the three groups represented by the formula (1-1) (the groups for R 1 to R 3 ) are preferably the same group having the same substituent.

In the compound of the exemplary embodiment, when two groups for R 1 to R 4 are selected from the groups represented by the formulae (1-1) to (1-6) and the remaining two groups for R 1 to R 4 are selected from the groups represented by the formulae (2-1) to (2-4), it is preferable that the two groups represented by the formulae (1-1) to (1-6) are represented by one of the formulae (1-1) to (1-6) and are the same group having the same substituent.

When three groups for R 1 to R 4 are selected from the groups represented by the formulae (1-1) to (1-6) and the remaining one group for R 1 to R 4 is selected from the groups represented by the formulae (2-1) to (2-4), it is preferable that the three groups represented by the formulae (1-1) to (1-6) are represented by one of the formulae (1-1) to (1-6) and are the same group having the same substituent.

For instance, when three groups each represented by the formula (1-1) are selected as the groups for R 1 to R 4 , it is preferable that the three groups are represented by the formula (1-1) and are the same group having the same substituent.

In the compound of the exemplary embodiment, when a plurality of groups each represented by the formula (2-1) are present as groups for R 1 to R 4 , the plurality of groups represented by the formula (2-1) are preferably the same group having the same substituent.

When a plurality of groups each represented by the formula (2-2) are present as groups for R 1 to R 4 , the plurality of groups represented by the formula (2-2) are preferably the same group having the same substituent.

When a plurality of groups each represented by the formula (2-3) are present as groups for R 1 to R 4 , the plurality of groups represented by the formula (2-3) are preferably the same group having the same substituent.

›MEANS FOR SOLVING THE PROBLEMS · 3 of 23

When a plurality of groups each represented by the formula (2-4) are present as groups for R 1 to R 4 , the plurality of groups represented by the formula (2-4) are preferably the same group having the same substituent.

Specifically, for instance, when two groups represented by the formula (2-1) are selected as the groups for R 1 and R 2 , one group represented by the formula (2-2) is selected as the group for R 3 , and one group represented by the formula (1-1) is selected as the group for R 4 , the two groups represented by the formula (2-1) (the groups for R 1 and R 2 ) are preferably the same group having the same substituent.

Moreover, for instance, when three groups represented by the formula (2-1) are selected as the groups for R 1 to R 3 , the three groups represented by the formula (2-1) (the groups for R 1 to R 3 ) are preferably the same group having the same substituent.

In the compound of the exemplary embodiment, when two groups for R 1 to R 4 are selected from the groups represented by the formulae (2-1) to (2-4) and the remaining two groups for R 1 to R 4 are selected from the groups represented by the formulae (1-1) to (1-6), it is preferable that the two groups represented by the formulae (2-1) to (2-4) are represented by one of the formulae (2-1) to (2-4) and are the same group having the same substituent.

When three groups for R 1 to R 4 are selected from the groups represented by the formulae (2-1) to (2-4) and the remaining one group for R 1 to R 4 is selected from the groups represented by the formulae (1-1) to (1-6), it is preferable that the three groups represented by the formulae (2-1) to (2-4) are represented by one of the formulae (2-1) to (2-4) and are the same group having the same substituent.

For instance, when three groups each represented by the formula (2-1) are selected as the groups for R 1 to R 4 , it is preferable that the three groups are represented by the formula (2-1) and are the same group having the same substituent.

The compound in the exemplary embodiment is preferably a compound represented by one of formulae (101) to (123).

In the formulae (101) to (123), D 1 each independently represents one of the groups represented by the formulae (1-1) to (1-6), D 2 each independently represents one of the groups represented by the formulae (2-1) to (2-4). A plurality of D 1 are mutually the same or different. A plurality of D 2 are mutually the same or different.

In the compound of the exemplary embodiment, D 1 in the formulae (101) to (123) are preferably mutually the same group.

In the compound of the exemplary embodiment, D 2 in the formulae (101) to (123) are preferably mutually the same group.

In other words, it is more preferable that D 1 are mutually the same group and D 2 are mutually the same group in the formulae (101) to (123) in the compound of the exemplary embodiment.

The compound in the exemplary embodiment is preferably one of the compounds respectively represented by one of the formulae (101), (106), (107), (110), (111) and (116) to (119).

In the formulae (1-1) to (1-6), X 1 to X 6 are preferably oxygen atoms.

In the formulae (1-1) to (1-6), X 1 to X 6 are also preferably sulfur atoms.

In the formulae (1-1) to (1-6), X 1 to X 6 are also preferably CR 151 R 152 .

In the compound of the exemplary embodiment, each of the groups represented by the formulae (1-1) to (1-6) is preferably the group represented by the formula (1-1), the group represented by the formula (1-2), or the group represented by the formula (1-4).

In the compound of the exemplary embodiment, each of the groups represented by the formulae (2-1) to (2-4) is preferably one of groups represented by formulae (2-5) to (2-17).

In the formulae (2-5) to (2-17), * each independently represents a bonding position to a carbon atom in a benzene ring in each of the formulae (11) to (13). D represents deuterium.

In the compound of the exemplary embodiment, each of the groups represented by the formulae (2-1) to (2-4) is preferably the group represented by the formula (2-2), the group represented by the formula (2-3), or the group represented by the formula (2-4).

In the compound of the exemplary embodiment, each of the groups represented by the formulae (2-1) to (2-4) is also preferably the group represented by the formula (2-1).

In the compound of the exemplary embodiment, the group represented by the formula (2-1) is also preferably the group represented by the formula (2-5) or the group represented by the formula (2-15).

When the compound in the exemplary embodiment has the group represented by the formula (2-1), R 161 to R 168 each independently preferably represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

When the compound in the exemplary embodiment has a group represented by the formula (2-1), it is also preferable that at least one of R 161 , R 163 , R 166 and R 168 is a substituent, the substituent each independently is a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and R 162 , R 164 , R 165 and R 167 are hydrogen atoms.

It is more preferable that the compound in the exemplary embodiment is one of compounds respectively represented by the formulae (101), (106), (107), (110), (111), and (116) to (119), where D 1 is each independently the group represented by the formula (1-1), the group represented by the formula (1-2) or the group represented by the formula (1-4), and D 2 is each independently the group represented by one of the formulae (2-5) to (2-14).

A plurality of D 1 are mutually the same or different. A plurality of D 2 are mutually the same or different.

The compound in the exemplary embodiment is preferably the compound represented by the formula (11).

The compound in the exemplary embodiment is also preferably the compound represented by the formula (12).

The compound in the exemplary embodiment is also preferably the compound represented by the formula (13).

›MEANS FOR SOLVING THE PROBLEMS · 4 of 23

In the formulae (1-1) to (1-6) and (2-1) to (2-4), R 101 to R 150 , R 151 , R 152 , R 161 to R 168 , R 171 to R 200 , R 171 to R 180 and R 61 to R 70 as the substituent each independently preferably a halogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted alkyl halide group having 1 to 6 carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted alkylthio group having 1 to 6 carbon atoms, or an unsubstituted arylthio group having 6 to 14 ring carbon atoms.

It is preferable that, in the formulae (1-1) to (1-6) and (2-1) to (2-4), R 101 to R 150 , R 151 , R 152 , R 161 to R 168 , R 171 to R 200 and R 61 to R 70 are each independently an unsubstituted aryl group having 6 to 14 ring carbon atoms or an unsubstituted alkyl group having 1 to 6 carbon atoms.

It is also preferable that, in the formulae (1-1) to (1-6), R 101 to R 150 and R 61 to R 70 are each a hydrogen atom, and R 151 and R 152 are each an unsubstituted aryl group having 6 to 14 ring carbon atoms or an unsubstituted alkyl group having 1 to 6 carbon atoms, and in the formulae (2-1) to (2-4), R 161 to R 168 and R 171 to R 200 are each a hydrogen atom.

When a sum of atomic weight of atoms forming each of R 1 to R 4 in the compound of the exemplary embodiment is calculated, it is preferable that a minimum sum M1 (min) among the sums of the groups corresponding to the groups represented by the formulae (1-1) to (1-6) and a maximum sum M2 (max) among the sums of the groups corresponding to the groups represented by the formulae (2-1) to (2-4) satisfies a relationship represented by a numerical formula (Numerical Formula 1) below.

Moreover, it is further preferable that the minimum sum M1 (min) among the sums and the maximum sum M2 (max) among the sums of the groups corresponding to the groups represented by the formulae (2-1) to (2-10) satisfy a relationship represented by a numerical formula (Numerical Formula 1X) below.

Moreover, it is particularly preferable that the minimum sum M1 (min) among the sums and the maximum sum M2 (max) among the sums of the groups corresponding to the groups represented by the formulae (2-1) to (2-10) satisfy a relationship represented by a numerical formula (Numerical Formula 1Y) below.

By satisfying the relationship represented by the numerical formula (Numerical Formula 1), (Numerical Formula 1X) or (Numerical Formula 1Y), the TADF properties are kept favorable and the sublimation temperature when the compound is sublimated and purified is easily lowered.

M 1(min)> M 2(max) (Numerical Formula 1)

140> M 1(min)− M 2(max) (Numerical Formula 1X)

110> M 1(min)− M 2(max) (Numerical Formula 1Y)

A numerical formula (Numerical Formula 1) will be described.

The compound in the exemplary embodiment will be described with an exemplary compound represented by the formula (11) in which R 1 is an unsubstituted 5H-benzofuro[3,2-c]carbazole group (C 18 H 10 ON), R 4 is a 5H-benzofuro[3,2-c]carbazole group (C 19 H 12 ON) substituted by a single methyl group, R 2 is an unsubstituted carbazole group (C 12 H 8 N), and R 3 is a carbazole group (C 13 H 10 N) substituted by a single methyl group.

The compound represented by the formula (11) having the above groups for R 1 to R 4 is defined as a compound A below.

At this time, a sum of atomic weights of atoms forming R 1 (C 18 H 10 ON) (hereinafter, also referred to as a “sum M R1 ”) is calculated as 12/18+10+16+14=256.

A sum of atomic weights of atoms forming R 4 (C 19 H 120 N) (hereinafter, also referred to as a “sum M R4 ”) is calculated as 12×19+12+16+14=270.

A sum of atomic weights of atoms forming R 2 (C 12 H 8 N) (hereinafter, also referred to as a “sum M R2 ”) is calculated as 12×12+8+14=166.

A sum of atomic weights of atoms forming R 3 (C 13 H 10 ON) (hereinafter, also referred to as a “sum M R3 ”) is calculated as 12×13+10+14=180.

R 1 and R 4 are groups corresponding to the groups represented by the formulae (1-1) to (1-6).

In a comparison between R 1 and R 4 in terms of the sum of the atomic weights, the sum M R4 >the sum M R1 in which the minimum sum M1 (min) is equal to the sum Mn.

R 2 and R 3 are groups corresponding to the groups represented by the formulae (2-1) to (2-4).

In a comparison between R 2 and R 3 in terms of the sum of the atomic weights, the sum M R3 >the sum M R2 in which the maximum sum M2 (max) is equal to the sum M R3 .

Accordingly, since the compound A satisfies “the sum M R1 >the sum M R3 ”, the compound A is a compound satisfying a relationship represented by the numerical formula (Numerical Formula 1).

Manufacturing Method of Compound According to Exemplary Embodiment

The compound according to the exemplary embodiment can be manufactured through, for instance, a process described later in Examples. The compound according to the exemplary embodiment can be manufactured, for instance, by application of known substitution reactions and/or materials depending on a target compound according to reactions described later in Examples.

Examples of the compound according to the exemplary embodiment include compounds represented by formulae (11-1), (12-1) to (12-2) and (13-1) to (13-2).

In the formula (11-1), D 1A , D 2A , D 1B , and D 2B respectively represent groups corresponding to numbers given to columns of D 1A , D 2A , D 1B , and D 2B in Tables 3 to 20 below.

In the formula (12-1), D 1A , D 2A , D 1B , and D 2B respectively represent groups corresponding to numbers given to columns of D 1A , D 2A , D 1B , and D 2B in Tables 3 to 20 below.

In the formula (12-2), D 1A , D 2A , D 1B , and D 2B respectively represent groups corresponding to numbers given to columns of D 1A , D 2A , D 1B , and D 2B in Tables 3 to 20 below.

›MEANS FOR SOLVING THE PROBLEMS · 5 of 23

In the formula (13-1), D 1A , D 2A , D 1B , and D 2B respectively represent groups corresponding to numbers given to columns of D 1A , D 2A , D 1B , and D 28 in Tables 3 to 20 below.

In the formula (13-2), D 1A , D 2A , D 1B , and D 2B respectively represent groups corresponding to numbers given to columns of D 1A , D 2A , D 1B , and D 2B in Tables 3 to 20 below.

In Tables 3 to 20 below, the numbers given to columns of D 1A , D 1A , D 1B , and D 2B correspond to numbers of later-described groups 1 to 36 and groups 1′ to 18′.

The groups 1 to 36 and groups 1′ to 18′ are shown below, * each independently represents a bonding position to a carbon atom of a benzene ring in each of the formulae (11-1), (12-1) to (12-2) and (13-1) to (13-2) and later-described formulae (11-2), (12-3) to (12-6) and (13-3) to (13-4). Me represents a methyl group. D represents deuterium.

For instance, in Table 3, a compound 1 represents a compound 1a represented by the formula (11-1) in which D 1A and D 1B are groups 1 and D 2A and D 2B are groups 1′, a compound 1b represented by the formula (12-1) in which D 1A and D 1B are groups 1 and D 2A and D 2B are groups 1′, a compound 1c represented by the formula (12-2) in which D 1A and D 1B are groups 1 and D 2A and D 2B are groups 1′, a compound 1 d represented by the formula (13-1) in which D 1A and D 1B are groups 1 and D 2A and D 2B are groups 1′, and a compound 1e represented by the formula (13-2) in which D 1A and 013 are groups 1 and D 2A and D 2B are groups 1′.

In other words, the compound 1 is any one of the compounds 1a to 1e.

A relationship between the compound 1 and the compounds 1a to 1e is shown in Table 1 below.

Herein, the compounds 1 to 540 and 1621 to 1728 are also referred to as a compound X. X is an integer from 1 to 540 and from 1621 to 1728. Specifically, the compound X represents compounds Xa to Xe.

A relationship between the compound X and the compounds Xa to Xe is shown in Table 2 below.

Examples of the compound according to the exemplary embodiment include compounds represented by the formulae (12-3) to (12-5), (13-3) and (11-2).

In the formula (12-3), D 1A , D 2A , D 2B , and D 2C respectively represent the groups denoted by the numbers shown in Tables 22 to 39.

In the formula (13-3), D 1A , D 2A , D 2B , and D 2C respectively represent the groups denoted by the numbers shown in Tables 22 to 39.

In the formula (12-4), D 1A , D 2A , D 2B , and D 2C respectively represent the groups denoted by the numbers shown in Tables 22 to 39.

In the formula (12-5), D 1A , D 2A , D 2B , and D 2C respectively represent the groups denoted by the numbers shown in Tables 22 to 39.

In the formula (11-2), D 1A , D 2A , D 2B , and D 2C respectively represent the groups denoted by the numbers shown in Tables 22 to 39.

In Tables 22 to 39 below, the numbers given to columns of D 1A , D 2A , D 1B , and D 2B correspond to numbers of the above-described groups 1 to 36 and groups 1′ to 18′.

For instance, in Table 22, a compound 541 represents a compound 541a represented by the formula (12-3) in which D 1A is the group 1 and D 2A , D 2B and D 2C are the groups 1′, a compound 541b represented by the formula (13-3) in which D 1A is the group 1 and D 2A , D 2B and D 2C are the groups 1′, a compound 541c represented by the formula (12-4) in which D 1A is the group 1 and D 2A , D 2B and D 2C are the groups 1′, a compound 541d represented by the formula (12-5) in which D 1A is the group 1 and D 2A , D 2B and D 2C are the groups 1′, and a compound 541e represented by the formula (11-2) in which D 1A is the group 1 and D 2A , D 2B and D 2C are the groups 1′.

In other words, the compound 541 is any one of the compounds 541a to 541e.

Herein, the compounds 541 to 1080 and 1729 to 1836 are also referred to as a compound Y. Y is an integer from 541 to 1080 and from 1729 to 1836. Specifically, the compound Y represents a compound Ya, Yb, Yc, Yd or Ye.

A relationship between the compound Y and the compounds Ya to Ye is shown in Table 21 below.

Examples of the compound according to the exemplary embodiment include compounds represented by the formulae (12-6) and (13-4).

In the formula (12-6), D 1A , D 1B , D 1C , and D 2A respectively represent the groups denoted by the numbers shown in Tables 41 to 58.

In the formula (13-4), D 1A , D 1B , D 1C , and D 2A respectively represent the groups denoted by the numbers shown in Tables 41 to 58.

In Tables 41 to 58 below, the numbers given to columns of D 1A , D 1B , D 1C , and D 2A , correspond to numbers of the above-described groups 1 to 36 and groups 1′ to 18′.

For instance, in Table 41, a compound 1081 represents a compound 1081a represented by the formula (12-6) in which D 1A , D 1B and D 1C are the groups 1 and D 2A is the group 1′, or a compound 1081b represented by the formula (13-4) in which D 1A , D 1B and D 1C are the groups 1 and D 2A is the group 1′.

In other words, the compound 1081 is the compound 1081a or 1081b.

Herein, the compounds 1081 to 1620 and 1837 to 1944 are also referred to as a compound Z. Z is an integer from 1081 to 1620 and from 1837 to 1944. Specifically, the compound Z represents a compound Za or a compound Zb.

A relationship between the compound Z and the compounds Za and Zb is shown in Table 40 below.

The compound in the exemplary embodiment is preferably the compound represented by the formula (103), more preferably a compound represented by a formula (103A).

In the formula (103A), D 1C is a group represented by a formula (1-4A) below, D 20 is a group represented by a formula (2-1). A plurality of D 20 in the formula (103A) are mutually the same group.

That “a plurality of D 20 are mutually the same group” means that all variables represented by the same signs in the formula (2-1) are the same. The “variables in the formula (2-1)” refer to R 161 to R 168 . Specifically, in the “groups represented by the formula (2-1)” representing the plurality of D 20 in the formula (103A), R 161 are the same, R 162 are the same, R 163 are the same, R 164 are the same, R 165 are the same, R 166 are the same, R 167 are the same, and R 168 are the same. In other words, three 020 in the formula (103A) are the same group having the same substituent.

›MEANS FOR SOLVING THE PROBLEMS · 6 of 23

In the formula (1-4A), X 40 represents an oxygen atom or a sulfur atom, R 131 to R 140 represent the same as R 131 to R 140 in the formula (1-4).

* represents a bonding position to a benzene ring in the formula (103A).

In the formula (1-4A), X 40 is preferably a sulfur atom.

In the formula (1-4A), X 40 is also preferably an oxygen atom.

In the compound represented by the formula (103A), the group represented by the formula (2-1) is preferably one of groups represented by formulae (2-5) and (2-9) to (2-17).

In the formulae (2-5) and (2-9) to (2-17), * each independently represents a bonding position to a benzene ring in the formula (103A), and D represents deuterium.

In the formulae (2-1), R 161 to R 168 are each independently preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In the formula (2-1), it is also preferable that at least one of R 161 , R 163 , R 166 and R 168 has a substituent, the substituent is each independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and R 162 , R 164 , R 165 and R 167 are each a hydrogen atom.

In the formula (2-1), when one or more of R 161 to R 168 are hydrogen atom(s), it is preferable that all of the hydrogen atom(s) are protium, one or more of the hydrogen atom(s) are deuterium, or all of the hydrogen atom(s) are deuterium.

In the formulae (1-4A) and (2-1), R 131 to R 140 and R 161 to R 168 as the substituent are each independently preferably a halogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted alkyl halide group having 1 to 6 carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted alkylthio group having 1 to 6 carbon atoms, or an unsubstituted arylthio group having 6 to 14 ring carbon atoms.

In the formulae (1-4A) and (2-1), R 131 to R 140 and R 161 to R 168 are each independently preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, or substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, further preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In the formulae (1-4A) and (2-1), R 131 to R 140 and R 161 to R 168 as the substituent are each independently more preferably an unsubstituted aryl group having 6 to 14 ring carbon atoms or an unsubstituted alkyl group having 1 to 6 carbon atoms.

In the formulae (1-4A) and (2-1), it is also preferable that R 137 is a substituent and R 137 as the substituent is a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and R 131 to R 136 and R 138 to R 140 are each a hydrogen atom.

In the formulae (1-4A) and (2-1), it is also preferable that R 131 to R 140 and R 161 to R 168 are each a hydrogen atom.

Examples of the compound according to the exemplary embodiment are shown below. The compound of the invention is by no means limited to the Examples. Me represents a methyl group.

Examples of the compound according to the exemplary embodiment are shown below. The compound of the invention is by no means limited to the Examples.

Second Exemplary Embodiment

Organic-EL-Device Material

An organic-EL-device material according to a second exemplary embodiment contains the compound according to the first exemplary embodiment (at least one of the compounds represented by the formulae (11) to (13).)

According to the second exemplary embodiment, the organic-EL-device material capable of decreasing a sublimation temperature when being sublimated and purified while maintaining TADF properties can be obtained.

The organic-EL-device material according to the second exemplary embodiment may further contain a compound other than the compound according to the first exemplary embodiment. When organic-EL-device material according to the second exemplary embodiment contains the compound other than the compound according to the first exemplary embodiment, the compound in the second exemplary embodiment may be solid or liquid.

Third Exemplary Embodiment

Organic EL Device

An arrangement of an organic EL device according to a third exemplary embodiment will be described below.

The organic EL device includes an anode, a cathode, and an at least one organic layer between the anode and the cathode. The organic layer typically includes a plurality of laminated layers formed of an organic compound. The organic layer may further include an inorganic compound. The organic EL device according to the exemplary embodiment includes a first organic layer between the anode and the cathode. The first organic layer contains at least one of the compounds represented by the formulae (11) to (13).

The first organic layer is, for instance, at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an emitting layer, an electron injecting layer, an electron transporting layer, a hole blocking layer and an electron blocking layer.

The first organic layer is preferably the emitting layer.

In the organic EL device of the exemplary embodiment, the first organic layer is the emitting layer.

›MEANS FOR SOLVING THE PROBLEMS · 7 of 23

In the exemplary embodiment, the organic layer may consist of the emitting layer as the first organic layer. Alternatively, the organic layer may further include, for instance, at least one layer selected from the group consisting of the hole injecting layer, the hole transporting layer, the electron injecting layer, the electron transporting layer, the hole blocking layer, and the electron blocking layer.

FIG. 1 schematically shows an exemplary structure of the organic EL device of the exemplary embodiment.

The organic EL device 1 includes a light-transmissive substrate 2 , an anode 3 , a cathode 4 , and an organic layer 10 provided between the anode 3 and the cathode 4 . The organic layer 10 includes a hole injecting layer 6 , a hole transporting layer 7 , an emitting layer 5 (the first organic layer), an electron transporting layer 8 , and an electron injecting layer 9 , which are sequentially layered on the anode 3 .

In the organic EL device 1 according to the exemplary embodiment, the emitting layer 5 contains the first compound.

The first compound is the compound according to the first exemplary embodiment (at least one of the compounds represented by the formulae (11) to (13)).

It is preferable that the emitting layer 5 does not contain a phosphorescent material (dopant material).

It is preferable that the emitting layer 5 does not contain a heavy metal complex and a phosphorescent rare-metal complex. Examples of the heavy metal complex herein include iridium complex, osmium complex, and platinum complex.

It is also preferable that the emitting layer 5 does not contain a metal complex.

In the organic EL device 1 according to the exemplary embodiment, the emitting layer 5 contains the first compound and further a second compound.

In this arrangement, the first compound is preferably a host material (sometimes referred to as a matrix material hereinafter), and the second compound is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a luminescent material hereinafter).

First Compound

The first compound is according to the first exemplary embodiment.

The first compound is preferably a delayed fluorescent compound.

Delayed Fluorescence

Delayed fluorescence is explained in “Yuki Hando-tai no Debaisu Bussei (Device Physics of Organic Semiconductors)” (edited by ADACHI, Chihaya, published by Kodansha, on pages 261-268). This document describes that, if an energy gap ΔE 13 of a fluorescent material between a singlet state and a triplet state is reducible, a reverse energy transfer from the triplet state to the singlet state, which usually occurs at a low transition probability, would occur at a high efficiency to express thermally activated delayed fluorescence (TADF). Further, a mechanism of generating delayed fluorescence is explained in FIG. 10.38 in the document. The first compound in the exemplary embodiment is preferably a compound exhibiting thermally activated delayed fluorescence generated by such a mechanism.

In general, emission of delayed fluorescence can be confirmed by measuring the transient PL (Photo Luminescence).

The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from the transient PL measurement. The transient PL measurement is a method of irradiating a sample with a pulse laser to excite the sample, and measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped. PL emission in TADF materials is classified into a light emission component from a singlet exciton generated by the first PL excitation and a light emission component from a singlet exciton generated via a triplet exciton. The lifetime of the singlet exciton generated by the first PL excitation is on the order of nanoseconds and is very short. Therefore, light emission from the singlet exciton rapidly attenuates after irradiation with the pulse laser.

On the other hand, the delayed fluorescence is gradually attenuated due to light emission from a singlet exciton generated via a triplet exciton having a long lifetime. As described above, there is a large temporal difference between the light emission from the singlet exciton generated by the first PL excitation and the light emission from the singlet exciton generated via the triplet exciton. Therefore, the luminous intensity derived from delayed fluorescence can be determined.

FIG. 2 shows a schematic diagram of an exemplary device for measuring the transient PL. An example of a method of measuring a transient PL using FIG. 2 and an example of behavior analysis of delayed fluorescence will be described.

A transient PL measuring device 100 in FIG. 2 includes: a pulse laser 101 capable of radiating a light having a predetermined wavelength; a sample chamber 102 configured to house a measurement sample; a spectrometer 103 configured to divide a light radiated from the measurement sample; a streak camera 104 configured to provide a two-dimensional image; and a personal computer 105 configured to import and analyze the two-dimensional image. A device for measuring the transient PL is not limited to the device described in the exemplary embodiment.

The sample to be housed in the sample chamber 102 is obtained by doping a matrix material with a doping material at a concentration of 12 mass % and forming a thin film on a quartz substrate.

The thin film sample housed in the sample chamber 102 is radiated with a pulse laser from the pulse laser 101 to excite the doping material. Emission is extracted in a direction of 90 degrees with respect to a radiation direction of the excited light. The extracted emission is divided by the spectrometer 103 to form a two-dimensional image in the streak camera 104 . As a result, the two-dimensional image is obtainable in which the ordinate axis represents a time, the abscissa axis represents a wavelength, and a bright spot represents a luminous intensity. When this two-dimensional image is taken out at a predetermined time axis, an emission spectrum in which the ordinate axis represents the luminous intensity and the abscissa axis represents the wavelength is obtainable. Moreover, when this two-dimensional image is taken out at the wavelength axis, a decay curve (transient PL) in which the ordinate axis represents a logarithm of the luminous intensity and the abscissa axis represents the time is obtainable.

›MEANS FOR SOLVING THE PROBLEMS · 8 of 23

For instance, a thin film sample A was manufactured as described above from a reference compound H1 as the matrix material and a reference compound D1 as the doping material and was measured in terms of the transient PL.

The decay curve was analyzed with respect to the above thin film sample A and a thin film sample B. The thin film sample B was manufactured in the same manner as described above from a reference compound H2 as the matrix material and the reference compound D1 as the doping material.

FIG. 3 shows decay curves obtained from transient PL obtained by measuring the thin film samples A and B.

As described above, an emission decay curve in which the ordinate axis represents the luminous intensity and the abscissa axis represents the time can be obtained by the transient PL measurement. Based on the emission decay curve, a fluorescence intensity ratio between fluorescence emitted from a singlet state generated by photo-excitation and delayed fluorescence emitted from a singlet state generated by inverse energy transfer via a triplet state can be estimated. In a delayed fluorescent material, a ratio of the intensity of the slowly decaying delayed fluorescence to the intensity of the promptly decaying fluorescence is relatively large.

Specifically, Prompt emission and Delay emission are present as emission from the delayed fluorescent material. Prompt emission is observed promptly when the excited state is achieved by exciting the compound of the exemplary embodiment with a pulse beam (i.e., a beam emitted from a pulse laser) having a wavelength absorbable by the delayed fluorescent material. Delay emission is observed not promptly when the excited state is achieved but after the excited state is achieved.

An amount of Prompt emission, an amount of Delay emission and a ratio between the amounts thereof can be obtained according to the method as described in “Nature 492, 234-238, 2012” (Reference Document 1). The amount of Prompt emission and the amount of Delay emission may be calculated using a device different from one described in Reference Document 1 or one shown in FIG. 2 .

In the exemplary embodiment, a sample manufactured by a method shown below is used for measuring delayed fluorescence of the first compound. For instance, the first compound is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. In order to prevent quenching due to oxygen, the sample solution is frozen and degassed and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.

The fluorescence spectrum of the sample solution is measured with a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of a 9,10-diphenylanthracene ethanol solution is measured under the same conditions. Using the fluorescence area intensities of both spectra, the total fluorescence quantum yield is calculated by an equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

In the exemplary embodiment, a measurement target compound (the first compound) preferably has a value of X D /X P is 0.05 or more, provided that the amount of Prompt emission is denoted by X P and the amount of Delay emission is denoted by X D .

Amounts of Prompt emission and Delay emission and a ratio of the amounts thereof in compounds other than the first compound herein are measured in the same manner as those of the first compound.

Second Compound

The second compound is preferably a fluorescent compound. The second compound may be a thermally activated delayed fluorescent compound or a compound exhibiting no thermally activated delayed fluorescence.

A fluorescent material is usable as the second compound in the exemplary embodiment. Specific examples of the fluorescent material include a bisarylaminonaphthalene derivative, aryl-substituted naphthalene derivative, bisarylaminoanthracene derivative, aryl-substituted anthracene derivative, bisarylaminopyrene derivative, aryl-substituted pyrene derivative, and bisarylamino Chrysene derivative, aryl-substituted chrysene derivative, bisarylaminofluoranthene derivative, aryl-substituted fluoranthene derivative, indenoperylene derivative, acenaphthofluoranthene derivative, pyromethene boron complex compound, compound having a pyromethene skeleton, metal complex of the compound having a pyrromethene skeleton, diketopyrrolopyrrole derivative, perylene derivative, and naphthacene derivative.

The second compound in the exemplary embodiment is also preferably represented by a formula (20) below.

The second compound is represented by the formula (20) below.

The second compound is preferably a fluorescent compound.

In the formula (20), X is a nitrogen atom, or a carbon atom bonded to Y.

Y is a hydrogen atom or a substituent.

R 21 to R 26 are each independently a hydrogen atom or a substituent, or at least one of a pair of R 21 and R 22 , a pair of R 22 and R 23 , a pair of R 24 and R 25 , or a pair of R 25 and R 26 are mutually bonded to form a ring.

Y and R 21 to R 26 each being the substituent are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy halide group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a halogen atom, a carboxy group, a substituted or unsubstituted ester group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, and a substituted or unsubstituted siloxanyl group.

›MEANS FOR SOLVING THE PROBLEMS · 9 of 23

Z 21 and Z 22 are each independently a substituent, or are mutually bonded to form a ring,

Z 21 and Z 22 as the substituent are each independently selected from the group consisting of a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy halide group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.

For instance, when a pair of R 25 and R 26 in the formula (20) is mutually bonded to form a ring, the second compound is represented by a formula (21) below.

In the formula (21), X, Y, R 21 to R 24 , Z 21 and Z 22 respectively represent the same as X, Y, R 21 to R 24 , Z 21 and Z 22 in the formula (20). R 27 to R 30 each independently represent a hydrogen atom or a substituent. When R 27 to R 30 are each independently the substituent, the substituent represents the same as the substituents for R 21 to R 24 .

When a pair of R 21 and R 22 in the formula (20) is mutually bonded to form a ring, the second compound is represented by a formula (20A) or (20B) below. However, a structure of the second compound is not limited to structures below.

In the formula (20A), X, Y and R 21 to R 26 respectively represent the same as X, Y and R 21 to R 26 in the formula (20). R 1A each independently represent a hydrogen atom or a substituent. When R 1A is the substituent, the substituent represents the same as the substituents for R 21 to R 26 . n3 is 4.

In the formula (20B), X, Y and R 21 to R 26 respectively represent the same as X, Y and R 21 to R 26 in the formula (20). RIB each independently represent a hydrogen atom or a substituent. When R 1B is the substituent, the substituent represents the same as the substituents for R 21 to R 26 . n4 is 4.

It is preferable that at least one of Z 21 or Z 22 (preferably both of Z 21 and Z 22 ) is a group selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy halide group having 1 to 30 carbon atoms, and substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.

It is more preferable that at least one of Z 21 or Z 22 is a group selected from the group consisting of a fluorine-substituted alkoxy group having 1 to 30 carbon atoms, a fluorine-substituted aryloxy group having 6 to 30 ring carbon atoms, and an aryloxy group having 6 to 30 ring carbon atoms and substituted with a fluoroalkyl group having 1 to 30 carbon atoms.

Further preferably, at least one of Z 21 or Z 22 is a fluorine-substituted alkoxy group having 1 to 30 carbon atoms. Furthermore preferably, both of Z 21 and Z 22 are a fluorine-substituted alkoxy group having 1 to 30 carbon atoms.

It is also preferable that both of Z 21 and Z 22 are the same to each other.

Meanwhile, it is also preferable that at least one of Z 21 or Z 22 is a fluorine atom. It is also more preferable that both of Z 21 and Z 22 are fluorine atoms.

It is also preferable that at least one of Z 21 or Z 22 is a group represented by a formula (20a).

In the formula (20a): A represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted alkyl halide group having 1 to 6 carbon atoms, or substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms: L2 represents a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms, or substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms; and m is 0, 1, 2, 3, 4, 5, 6 or 7. When m is 2, 3, 4, 5, 6 or 7, a plurality of L2 are mutually the same or different. m is preferably 0, 1 or 2. When m is 0, A is directly bonded to 0 (oxygen atom).

When Z 21 and Z 22 of the formula (20) are each the group represented by the formula (20a), the second compound is represented by a formula (22).

The second compound is also preferably represented by the formula (22).

In the formula (22), X, Y bonded to a carbon atom as X, and R 21 to R 26 represent the same as X, Y and R 21 to R 26 in the formulae (20). A 21 and A 22 represent the same as A in the formula (20a) and may be mutually the same or different. L 21 and L 22 represent the same as L 2 in the formula (20a) and may be mutually the same or different. m1 and m2 are each independently 0, 1, 2, 3, 4, 5, 6 or 7, preferably 0, 1 or 2. When m1 is 2, 3, 4, 5, 6 or 7, a plurality of L 21 are mutually the same or different. When m2 is 2, 3, 4, 5, 6 or 7, a plurality of L 22 are mutually the same or different. When m1 is 0, A 21 is directly bonded to O (oxygen atom). When m2 is 0, A 22 is directly bonded to O (oxygen atom).

At least one of A or L 2 in the formula (20a) is preferably substituted with a halogen atom, more preferably substituted with a fluorine atom.

A in the formula (20a) is more preferably a perfluoroalkyl group having 1 to 6 carbon atoms or a perfluoroaryl group having 6 to 12 carbon atoms, further preferably a perfluoroalkyl group having 1 to 6 carbon atoms.

L 2 in the formula (20a) is more preferably a perfluoroalkylene group having 1 to 6 carbon atoms or a perfluoroarylene group having 6 to 12 carbon atoms, further preferably a perfluoroalkylene group having 1 to 6 carbon atoms.

Specifically, it is also preferable that the second compound is a compound represented by a formula (22a).

In the formula (22a): X represents the same as X in the formula (20). Y bonded to a carbon atom as X represents the same as Y in the formula (20).

R 21 to R 26 each independently represent the same as R 21 to R 26 in the formula (20).

›MEANS FOR SOLVING THE PROBLEMS · 10 of 23

m3 is in a range from 0 to 4.

m4 is in a range from 0 to 4.

m3 and m4 are mutually the same or different.

In the formulae (20), (21), (22) and (22a): X is a carbon atom bonded to Y; and is a hydrogen atom or a substituent.

Y as the substituent is preferably a substituent selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms and substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

In the formulae (20), (21), (22) and (22a), it is more preferable that X is a carbon atom bonded to Y; Y is a hydrogen atom or a substituent; Y as the substituent is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; when Y as the substituent is an aryl group having 6 to 30 ring carbon atoms having a substituent, the substituent is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy halide group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 ring carbon atoms and substituted by an alkyl group having 1 to 30 carbon atoms.

In the second compound, Z 21 and Z 22 may be mutually bonded to form a ring. However, it is preferable that Z 21 and Z 22 are not mutually bonded.

In the formulae (20), (22) and (22a), at least one of R 21 , R 23 , R 24 or R 26 is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms.

In the formulae (20), (22) and (22a), R 21 , R 23 , R 24 and R 26 are more preferably each a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms. In this case, R 22 and R 25 are preferably hydrogen atoms.

In the formulae (20), (22) and (22a), at least one of R 21 , R 23 , R 24 or R 26 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

In the formulae (20), (22) and (22a), R 21 , R 23 , R 24 and R 26 are more preferably each a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. In this case, R 22 and R 25 are preferably hydrogen atoms.

In the formulae (20), (22) and (22a), it is more preferable that R 21 , R 23 , R 24 and R 26 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), or an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 12 ring carbon atoms) and substituted with an alkyl group having 1 to 30 carbon atoms; and R 22 and R 25 are hydrogen atoms.

In the formula (21), at least one of R 21 , R 23 or R 24 is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms.

In the formula (21), R 21 , R 23 and R 24 are more preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms. In this case, R 22 is preferably a hydrogen atom.

In the formula (21), at least one of R 21 , R 23 or R 24 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

In the formula (21), R 21 , R 23 and R 24 are more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. In this case, R 22 is preferably a hydrogen atom.

In the formula (21): it is more preferable that R 21 , R 23 , and R 24 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), or an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 12 ring carbon atoms) and substituted with an alkyl group having 1 to 30 carbon atoms; and R 22 is a hydrogen atom.

In the second compound, examples of the fluorine-substituted alkoxy group include 2,2,2-trifluoroethoxy group, 2,2-difluoroethoxy group, 2,2,3,3,3-pentafluoro-1-propoxy group, 2,2,3,3-tetrafluoro-1-propoxy group, 1,1,1,3,3,3-hexafluoro-2-propoxy group, 2,2,3,3,4,4,4-heptafluoro-1-butyloxy group, 2,2,3,3,4,4-hexafluoro-1-butyloxy group, nonafluoro-tertiary-butyloxy group, 2,2,3,3,4,4,5,5,5-nonafluoropentanoxy group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoxy group, 2,3-bis(trifluoromethyl)-2,3-butanedioxy group, 1,1,2,2-tetra(trifluoromethyl)ethylene glycoxy group, 4,4,5,5,6,6,6-heptafluorohexane-1,2-dioxy group, and 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononane-1,2-dioxy group.

In the second compound, examples of the fluorine-substituted aryloxy group or the aryloxy group substituted with a fluoroalkyl group include a pentafluorophenoxy group, 3,4,5-trifluorophenoxy group, 4-trifluoromethylphenoxy group, 3,5-bistrifluoromethylphenoxy group, 3-fluoro-4-trifluoromethylphenoxy group, 2,3,5,6-tetrafluoro-4-trifluoromethylphenoxy group, 4-fluorocatecholato group, 4-trifluoromethylcatecholato group, and 3,5-bistrifluoromethylcatecholato group.

A substituent of the second compound that is “substituted or unsubstituted” is preferably a substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, alkyl group having 1 to 30 carbon atoms, alkyl halide group having 1 to 30 carbon atoms, cycloalkyl group having 3 to 30 ring carbon atoms, cyano group, amino group, substituted amino group, halogen atom, alkoxy group having 1 to 30 carbon atoms, aryloxy group having 6 to 30 ring carbon atoms, arylthio group having 6 to 30 carbon atoms, aralkyl group having 7 to 30 carbon atoms, substituted phosphoryl group, substituted silyl group, nitro group, carboxy group, alkenyl group having 2 to 30 carbon atoms, alkynyl group 2 to 30 carbon atoms, alkylthio group 1 to 30 carbon atoms, alkylsilyl group 3 to 30 carbon atoms, arylsilyl group having 6 to 30 ring carbon atoms, and hydroxy group.

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The substituent of the second compound that is “substituted or unsubstituted” is more preferably a substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, alkyl group having 1 to 30 carbon atoms, alkyl halide group having 1 to 30 carbon atoms, and cycloalkyl group having 3 to 30 ring carbon atoms.

The substituent of the second compound that is “substituted or unsubstituted” is further preferably a substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 12 ring atoms, alkyl group having 1 to 6 carbon atoms, alkyl halide group having 1 to 6 carbon atoms, and cycloalkyl group having 3 to 12 ring carbon atoms.

When the second compound is a fluorescent compound, the second compound preferably emits light having a main peak wavelength in a range from 400 nm to 700 nm.

Herein, the main peak wavelength means a peak wavelength of an emission spectrum exhibiting a maximum luminous intensity among fluorescence spectra measured in a toluene solution in which a measurement target compound is dissolved at a concentration ranging from 10 −6 mol/l to 10 −5 mol/l. A spectrophotofluorometer (F-7000 manufactured by Hitachi High-Tech Science Corporation) is used as a measurement device.

The second compound preferably exhibits red or green light emission.

Herein, the red light emissions refers to a light emission in which a main peak wavelength of fluorescence spectrum is in a range from 600 nm to 660 nm.

When the second compound is a red fluorescent compound, the main peak wavelength of the second compound is preferably in a range from 600 nm to 660 nm, more preferably in a range from 600 nm to 640 nm, further preferably in a range from 610 nm to 630 nm.

Herein, the green light emissions refers to a light emission in which a main peak wavelength of fluorescence spectrum is in a range from 500 nm to 560 nm.

When the second compound is a green fluorescent compound, the main peak wavelength of the second compound is preferably in a range from 500 nm to 560 nm, more preferably in a range from 500 nm to 540 nm, further preferably in a range from 510 nm to 530 nm.

Herein, the blue light emissions refers to a light emission in which a main peak wavelength of fluorescence spectrum is in a range from 430 nm to 480 nm.

When the second compound is a blue fluorescent compound, the main peak wavelength of the second compound is preferably in a range from 430 nm to 480 nm, more preferably in a range from 445 nm to 480 nm.

Manufacturing Method of Second Compound

The second compound can be manufactured by a known method.

Examples of the second compound according to the exemplary embodiment are shown below. The second compound of the invention is by no means limited to the Examples.

A coordinate bond between a boron atom and a nitrogen atom in a pyrromethene ekeleton is shown by various means such as a solid line, a broken line, an arrow, and omission. Herein, the coordinate bond is shown by a solid line or a broken line, or the description of the coordinate bond is omitted.

Relationship Between First Compound and Second Compound in Emitting Layer

In the organic EL device 1 of the exemplary embodiment, a singlet energy S 1 (Mat1) of the first compound and a singlet energy S 1 (Mat2) of the second compound preferably satisfy a relationship of a numerical formula (Numerical Formula 3).

S 1 (Mat1)> S 1 (Mat2) (Numerical Formula 3)

An energy gap T 77K (Mat1) at 77 [K] of the first compound is preferably larger than an energy gap T 77K (Mat2) at 77 [K] of the second compound. In other words, a relationship of the following numerical formula (Numerical Formula 5) is preferably satisfied.

T 77K (Mat1)> T 77K (Mat2) (Numerical Formula 5)

When the organic EL device 1 of the exemplary embodiment emits light, it is preferable that the second compound in the emitting layer 5 mainly emits light.

Relationship Between Triplet Energy and Energy Gap at 77K

Here, a relationship between a triplet energy and an energy gap at 77K will be described. In the exemplary embodiment, the energy gap at 77 [K] is different from a typical triplet energy in some aspects.

Triplet energy is measured as follows. Firstly, a solution in which a compound (measurement target) is dissolved in an appropriate solvent is encapsulated in a quartz glass tube to prepare a sample. A phosphorescent spectrum (ordinate axis: phosphorescent luminous intensity, abscissa axis: wavelength) of the sample is measured at a low temperature (77K). A tangent is drawn to the rise of the phosphorescent spectrum close to the short-wavelength region. The triplet energy is calculated by a predetermined conversion equation based on a wavelength value at an intersection of the tangent and the abscissa axis.

Here, the thermally activated delayed fluorescent compound among the compounds of the exemplary embodiment is preferably a compound having a small ΔST. When ΔST is small, intersystem crossing and inverse intersystem crossing are likely to occur even at a low temperature (77K), so that the singlet state and the triplet state coexist. As a result, the spectrum to be measured in the same manner as the above includes emission from both the singlet state and the triplet state. Although it is difficult to distinguish the emission from the singlet state from the emission from the triplet state, the value of the triplet energy is basically considered dominant.

Accordingly, in the exemplary embodiment, the triplet energy is measured by the same method as a typical triplet energy T, but a value measured in the following manner is referred to as an energy gap T 77K in order to differentiate the measured energy from the typical triplet energy in a strict meaning. The measurement target compound is dissolved in EPA (diethylether:isopentane:ethanol=5:5:2 in volume ratio) at a concentration of 10 μmol/L, and the obtained solution is encapsulated in a quartz cell to provide a measurement sample. A phosphorescent spectrum (ordinate axis: phosphorescent luminous intensity, abscissa axis: wavelength) of the sample is measured at a low temperature (77K). A tangent is drawn to the rise of the phosphorescent spectrum close to the short-wavelength region. An energy amount is calculated by a conversion equation below based on a wavelength value λ edge [nm] at an intersection of the tangent and the abscissa axis and is defined as an energy gap T 77K at 77 [K].

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T 77K [eV]=1239.8/λ edge Conversion Equation (F1):

The tangent to the rise of the phosphorescence spectrum close to the short-wavelength region is drawn as follows. While moving on a curve of the phosphorescence spectrum from the short-wavelength region to the maximum spectral value closest to the short-wavelength region among the maximum spectral values, a tangent is checked at each point on the curve toward the long-wavelength of the phosphorescence spectrum. An inclination of the tangent is increased along the rise of the curve (i.e., a value of the ordinate axis is increased). A tangent drawn at a point of the maximum inclination (i.e., a tangent at an inflection point) is defined as the tangent to the rise of the phosphorescence spectrum close to the short-wavelength region.

The maximum with peak intensity being 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum closest to the short-wavelength region. The tangent drawn at a point of the maximum spectral value being closest to the short-wavelength region and having the maximum inclination is defined as a tangent to the rise of the phosphorescence spectrum close to the short-wavelength region.

For phosphorescence measurement, a spectrophotofluorometer body F-4500 (manufactured by Hitachi High-Technologies Corporation) is usable. Any device for phosphorescence measurement is usable. A combination of a cooling unit, a low temperature container, an excitation light source and a light-receiving unit may be used for phosphorescence measurement.

Singlet Energy S 1

A method of measuring a singlet energy S 1 with use of a solution (occasionally referred to as a solution method) is exemplified by a method below.

A toluene solution in which a measurement target compound is dissolved at a concentration of 10 μmol/L is prepared and is encapsulated in a quartz cell to provide a measurement sample. Absorption spectrum (ordinate axis: absorption intensity, abscissa axis: wavelength) of the sample is measured at the normal temperature (300K). A tangent is drawn to the fall of the absorption spectrum close to the long-wavelength region, and a wavelength value λedge (nm) at an intersection of the tangent and the abscissa axis is obtained. The wavelength value λedge (nm) is substituted in a conversion equation (F2) below to calculate a singlent energy.

S 1 [eV]=1239.85/λedge Conversion Equation (F2):

Any device for measuring absorption spectrum is usable. For instance, a spectrophotometer (U3310 manufactured by Hitachi, Ltd.) is usable.

The tangent to the fall of the absorption spectrum close to the long-wavelength region is drawn as follows. While moving on a curve of the absorption spectrum from the maximum spectral value closest to the long-wavelength region in a long-wavelength direction, a tangent at each point on the curve is checked. An inclination of the tangent is decreased and increased in a repeated manner as the curve falls (i.e., a value of the ordinate axis is decreased). A tangent drawn at a point of the minimum inclination closest to the long-wavelength region (except when absorbance is 0.1 or less) is defined as the tangent to the fall of the absorption spectrum close to the long-wavelength region.

The maximum absorbance of 0.2 or less is not included in the above-mentioned maximum absorbance close to the long-wavelength region.

In the exemplary embodiment, a difference (S 1 -T 77K ) between the singlet energy S 1 and the energy gap T 77K at 77[K] is defined as ΔST.

In the exemplary embodiment, a difference ΔST(Mat1) between the singlet energy S 1 (Mat1) of the first compound and the energy gap T 77K (Mat1) at 77[K] of the the first compound is preferably less than 0.3 eV, more preferably less than 0.2 eV, further preferably less than 0.1 eV. In other words, ΔST(Mat1) preferably satisfies a numerical formula ((Numerical Formula 1A), (Numerical Formula 1B) or (Numerical Formula 1C)) below.

Δ ST (Mat1)= S 1 (Mat1)− T 77K (Mat1)<0.3 eV (Numerical Formula 1A)

Δ ST (Mat1)= S 1 (Mat1)− T 77K (Mat1)<0.2 eV (Numerical Formula 1B)

Δ ST (Mat1)= S 1 (Mat1)− T 77K (Mat1)<0.1 eV (Numerical Formula 10)

The organic EL device 1 in the exemplary embodiment preferably emits red light or green light.

When the organic EL device 1 in the exemplary embodiment emits green light, a main peak wavelength of the light from the organic EL device 1 is preferably in a range from 500 nm to 560 nm.

When the organic EL device 1 in the exemplary embodiment emits red light, a main peak wavelength of the light from the organic EL device 1 is preferably in a range from 600 nm to 660 nm.

When the organic EL device 1 in the exemplary embodiment emits blue light, a main peak wavelength of the light from the organic EL device 1 is preferably in a range from 430 nm to 480 nm.

A main peak wavelength of light from an organic EL device is measured as follows.

Voltage is applied on the organic EL device such that a current density was 10 mA/cm 2 , where spectral radiance spectrum is measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.).

In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the luminous intensity is maximized is measured, and this is taken as the main peak wavelength (unit: nm).

Film Thickness of Emitting Layer

A film thickness of the emitting layer of the organic EL device 1 in the exemplary embodiment is preferably in a range of 5 nm to 50 nm, more preferably in a range of 7 nm to 50 nm, further preferably in a range of 10 nm to 50 nm. When the film thickness of the emitting layer is 5 nm or more, the formation of the emitting layer and the adjustment of the chromaticity are easy. When the film thickness of the emitting layer is 50 nm or less, an increase in the drive voltage is likely to be reducible.

Content Ratio of Compounds in Emitting Layer

Content ratios of the first and second compounds in the emitting layer 5 are, for instance, preferably determined as follows.

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The content ratio of the first compound is preferably in a range from 10 mass % to 80 mass %, more preferably in a range from 10 mass % to 60 mass %, further preferably in a range from 20 mass % to 60 mass %.

The content ratio of the second compound is preferably in a range from 0.01 mass % to 10 mass %, more preferably in a range from 0.01 mass % to 5 mass %, further preferably in a range from 0.01 mass % to 1 mass %.

It should be noted that the emitting layer 5 of the exemplary embodiment may further contain material(s) other than the first and second compounds.

The emitting layer 5 may include a single type of the first compound or may include two or more types of the first compound. The emitting layer 5 may include a single type of the second compound or may include two or more types of the second compound.

TADF Mechanism

FIG. 4 shows an example of a relationship between energy levels of the first compound and the second compound in the emitting layer. In FIG. 4 , S0 represents a ground state. S1(Mat1) represents the lowest singlet state of the first compound. T1(Mat1) represents the lowest triplet state of the first compound. S1(Mat2) represents the lowest triplet state of the second compound. T1(Mat2) represents the lowest triplet state of the second compound.

A dashed arrow directed from S1(Mat1) to S1(Mat2) in FIG. 4 represents Förster energy transfer from the lowest singlet state of the first compound to the lowest singlet state of the second compound.

As shown in FIG. 4 , when a compound having a small ΔST(Mat1) is used as the first compound, inverse intersystem crossing from the lowest triplet state T1(Mat1) to the lowest singlet state S1(Mat1) can be caused by a heat energy. Subsequently, Förster energy transfer from the lowest singlet state S1(Mat1) of the first compound the second compound occurs to generate the lowest singlet state S1(Mat2). Consequently, fluorescence from the lowest singlet state S1(Mat2) of the second compound can be observed. It is inferred that the internal quantum efficiency can be theoretically raised up to 100% also by using delayed fluorescence by the TADF mechanism.

The organic EL device 1 according to the third exemplary embodiment contains the first compound that is the compound according to the first exemplary embodiment (at least one of the compounds represented by the formulae (11) to (13)), and the second compound having the singlet energy smaller than that of the first compound in the emitting layer 5 .

The organic EL device according to the third exemplary embodiment is applicable to an electronic device such as a display device and a light-emitting device.

An arrangement of an organic EL device 1 will be further described. The description of the reference signs may be omitted.

Substrate

A substrate is used as a support for the organic EL device. For instance, glass, quartz, plastics and the like are usable as the substrate. A flexible substrate is also usable. The flexible substrate is a bendable substrate, which is exemplified by a plastic substrate. Examples of the material for the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Moreover, an inorganic vapor deposition film is also usable.

Anode

Metal having a large work function (specifically, 4.0 eV or more), an alloy, an electrically conductive compound and a mixture thereof are preferably used as the anode formed on the substrate. Specific examples of the material include ITO (Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chrome (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of a metal material (e.g., titanium nitride) are usable.

The material is typically formed into a film by a sputtering method. For instance, the indium oxide-zinc oxide can be formed into a film by the sputtering method using a target in which zinc oxide in a range from 1 mass % to 10 mass % is added to indium oxide. Moreover, for instance, the indium oxide containing tungsten oxide and zinc oxide can be formed by the sputtering method using a target in which tungsten oxide in a range from 0.5 mass % to 5 mass % and zinc oxide in a range from 0.1 mass % to 1 mass % are added to indium oxide. In addition, the anode may be formed by a vacuum deposition method, a coating method, an inkjet method, a spin coating method or the like.

Among the EL layers formed on the anode, since the hole injecting layer adjacent to the anode is formed of a composite material into which holes are easily injectable irrespective of the work function of the anode, a material usable as an electrode material (e.g., metal, an alloy, an electroconductive compound, a mixture thereof, and the elements belonging to the group 1 or 2 of the periodic table) is also usable for the anode.

A material having a small work function such as elements belonging to Groups 1 and 2 in the periodic table of the elements, specifically, an alkali metal such as lithium (Li) and cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys (e.g., MgAg and AlLi) including the alkali metal or the alkaline earth metal, a rare earth metal such as europium (Eu) and ytterbium (Yb), alloys including the rare earth metal are also usable for the anode. It should be noted that the vacuum deposition method and the sputtering method are usable for forming the anode using the alkali metal, alkaline earth metal and the alloy thereof. Further, when a silver paste is used for the anode, the coating method and the inkjet method are usable.

Cathode

It is preferable to use metal, an alloy, an electroconductive compound, and a mixture thereof, which have a small work function (specifically, 3.8 eV or less) for the cathode. Examples of the material for the cathode include elements belonging to Groups 1 and 2 in the periodic table of the elements, specifically, the alkali metal such as lithium (Li) and cesium (Cs), the alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys (e.g., MgAg and AlLi) including the alkali metal or the alkaline earth metal, the rare earth metal such as europium (Eu) and ytterbium (Yb), and alloys including the rare earth metal.

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It should be noted that the vacuum deposition method and the sputtering method are usable for forming the cathode using the alkali metal, alkaline earth metal and the alloy thereof. Further, when a silver paste is used for the cathode, the coating method and the inkjet method are usable.

By providing the electron injecting layer, various conductive materials such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide may be used for forming the cathode regardless of the work function. The conductive materials can be formed into a film using the sputtering method, inkjet method, spin coating method and the like.

Hole Injecting Layer

The hole injecting layer is a layer containing a substance exhibiting a high hole injectability. Examples of the substance exhibiting a high hole injectability include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chrome oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

In addition, the examples of the highly hole-injectable substance further include: an aromatic amine compound, which is a low-molecule compound, such that 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl(abbreviation: DRAB), 4,4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1); and dipyrazino[2,34:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

In addition, a high polymer compound (e.g., oligomer, dendrimer and polymer) is usable as the substance exhibiting a high hole injectability. Examples of the high polymer compound include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-N′-phenylamino}phenyl)methacrylamido] (abbreviation: PTPDMA), and poly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Moreover, an acid-added high polymer compound such as poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonic acid) (PEDOT/PSS) and polyaniline/poly (styrene sulfonic acid)(PAni/PSS) are also usable.

Hole Transporting Layer

The hole transporting layer is a layer containing a highly hole-transporting substance. An aromatic amine compound, carbazole derivative, anthracene derivative and the like are usable for the hole transporting layer. Specific examples of a material for the hole transporting layer include an aromatic amine compound such as 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (abbreviation: TPD), 4-phenyl-4′-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BAFLP), 4,4′-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4′-bis[N-(spiro-9,9′-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above-described substances mostly have a hole mobility of 10 −6 cm 2 /(V·s) or more.

For the hole transporting layer, a carbazole derivative such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA) and an anthracene derivative such as t-BuDNA, DNA, and DPAnth may be used. A high polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) is also usable.

However, in addition to the above substances, any substance exhibiting a higher hole transportability than an electron transportability may be used. It should be noted that the layer containing the substance exhibiting a high hole transportability may be not only a single layer but also a laminate of two or more layers formed of the above substance.

When the hole transporting layer includes two or more layers, one of the layers with a larger energy gap is preferably provided closer to the emitting layer. An example of the material with a larger energy gap is HT-2 used in later-described Examples.

Electron Transporting Layer

The electron transporting layer is a layer containing a highly electron-transporting substance. For the electron transporting layer, 1) a metal complex such as an aluminum complex, beryllium complex, and zinc complex, 2) a hetero aromatic compound such as imidazole derivative, benzimidazole derivative, azine derivative, carbazole derivative, and phenanthroline derivative, and 3) a high polymer compound are usable. Specifically, as a low-molecule organic compound, a metal complex such as Alq, tris(4-methyl-8-quinolinato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeEq2), BAlq, Znq, ZnPBO and ZnBTZ is usable. In addition to the metal complex, a heteroaromatic compound such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4′-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviation: BzOs) is usable. In the exemplary embodiment, a benzimidazole compound is preferably usable. The above-described substances mostly have an electron mobility of 10 −6 cm 2 /(V·s) or more. It should be noted that any substance other than the above substance may be used for the electron transporting layer as long as the substance exhibits a higher electron transportability than the hole transportability. The electron transporting layer may be provided in the form of a single layer or a laminate of two or more layers of the above substance(s).

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Moreover, a high polymer compound is usable for the electron transporting layer. For instance, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like are usable.

Electron Injecting Layer

The electron injecting layer is a layer containing a highly electron-injectable substance. Examples of a material for the electron injecting layer include an alkali metal, alkaline earth metal and a compound thereof, examples of which include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx). In addition, the alkali metal, alkaline earth metal or the compound thereof may be added to the substance exhibiting the electron transportability in use. Specifically, for instance, magnesium (Mg) added to Alq may be used. In this case, the electrons can be more efficiently injected form the anode.

Alternatively, the electron injecting layer may be provided by a composite material in a form of a mixture of the organic compound and the electron donor. Such a composite material exhibits excellent electron injectability and electron transportability since electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, the above examples (e.g., the metal complex and the hetero aromatic compound) of the substance forming the electron transporting layer are usable. As the electron donor, any substance exhibiting electron donating property to the organic compound is usable. Specifically, the electron donor is preferably alkali metal, alkaline earth metal and rare earth metal such as lithium, cesium, magnesium, calcium, erbium and ytterbium. The electron donor is also preferably alkali metal oxide and alkaline earth metal oxide such as lithium oxide, calcium oxide, and barium oxide. Moreover, a Lewis base such as magnesium oxide is usable. Further, the organic compound such as tetrathiafulvalene (abbreviation: TTF) is usable.

Layer Formation Method

A method for forming each layer of the organic EL device in the third exemplary embodiment is subject to no limitation except for the above particular description. However, known methods of dry film-forming such as vacuum deposition, sputtering, plasma or ion plating and wet film-forming such as spin coating, dipping, flow coating or ink jet printing are applicable.

Film Thickness

A thickness of each of the organic layers in the organic EL device according to the third exemplary embodiment is not limited except for the above particular description. In general, the thickness preferably ranges from several nanometers to 1 μm in order to avoid defects such as a pin hole and to prevent efficiency from being deteriorated since a high voltage needs to be applied.

Fourth Exemplary Embodiment

An arrangement of an organic EL device according to a fourth exemplary embodiment will be described below. In the description of the fourth exemplary embodiment, the same components as those in the third exemplary embodiment are denoted by the same reference signs and names to simplify or omit an explanation of the components. In the fourth exemplary embodiment, any materials and compounds that are not specified may be the same as those in the third exemplary embodiment.

The organic EL device according to the fourth exemplary embodiment is different from the organic EL device according to the third exemplary embodiment in that the emitting layer further includes a third compound. The rest of the arrangement of the organic EL device according to the fourth exemplary embodiment is the same as in the third exemplary embodiment.

Specifically, in the fourth exemplary embodiment, the emitting layer as a first organic layer contains the first compound, the second compound and the third compound.

In the fourth exemplary embodiment, the first compound is preferably a host material, the second compound is preferably a dopant material, and the third compound is preferably a material that disperses the dopant material in the emitting layer.

Third Compound

The third compound may be a thermally activated delayed fluorescent compound or a compound exhibiting no thermally activated delayed fluorescence.

The third compound is not particularly limited, but is preferably a compound other than an amine compound. Although the third compound may be a carbazole derivative, dibenzofuran derivative, or dibenzothiophene derivative, the third compound is not limited thereto.

It is also preferable that the third compound has at least one of a partial structure represented by a formula (31), a partial structure represented by a formula (32), a partial structure represented by a formula (33) and a partial structure represented by a formula (34) in one molecule.

In the formula (31), Y 31 to Y 36 each independently represent a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound.

At least one of Y 31 to Y 36 is a carbon atom bonded to another atom in the molecule of the third compound.

In the formula (32), Y 41 to Y 48 each independently represent a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound.

At least one of Y 41 to Y 48 is a carbon atom bonded to another atom in the molecule of the third compound.

X 30 represents a nitrogen atom bonded to another atom in the molecule of the third compound, an oxygen atom, or a sulfur atom.

The mark * in the formulae (33) to (34) each independently shows a bonding position with another atom or another structure in the molecule of the third compound.

In the formula (32), it is also preferable that at least two of Y 41 to Y 48 are carbon atoms bonded to other atoms in the molecule of the third compound to form a cyclic structure including the carbon atoms.

For instance, the partial structure represented by the formula (32) is preferably any one selected from the group consisting of partial structures represented by formulae (321), (322), (323), (324), (325) and (326).

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In the formulae (321) to (326), X 30 each independently represents a nitrogen atom bonded to another atom in the molecule of the third compound, an oxygen atom, or a sulfur atom.

Y 41 to Y 48 each independently represent a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound.

X 31 each independently represents a nitrogen atom bonded to another atom in the molecule of the third compound, an oxygen atom, a sulfur atom, or a carbon atom bonded to another atom in the molecule of the third compound.

Y 6 to Y 64 each independently represent a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound.

In the exemplary embodiments, the third compound preferably has the partial structure represented by the formula (323) among those represented by the formulae (323) to (326).

The partial structure represented by the formula (31) is preferably included in the third compound as at least one group selected from the group consisting of a group represented by a formula (33) and a group represented by a formula (34) below.

It is also preferable that the third compound has at least one of the partial structures represented by the formulae (33) and (34). Since bonding positions are situated in meta positions as shown in the partial structures represented by the formulae (33) and (34), an energy gap T 77K (Mat3) at 77 [K] of the second compound can be kept high.

In the formula (33), Y 31 , Y 32 , Y 34 and Y 36 are each independently a nitrogen atom or CR 31 .

In the formula (34), Y 32 , Y 34 and Y 36 are each independently a nitrogen atom or CR 31 .

In the formulae (33) and (34), R 31 each independently represents a hydrogen atom or a substituent.

R 31 as the substituent is each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted germanium group, a substituted phosphine oxide group, a halogen atom, a cyano group, a nitro group, and a substituted or unsubstituted carboxy group.

The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms for R 31 is preferably a non-fused ring.

The mark * in the formulae (33) and (34) each independently shows a bonding position with another atom or another structure in the molecule of the third compound.

In the formula (33), Y 31 , Y 32 , Y 34 and Y 36 are each independently preferably CR 31 , in which a plurality of R 31 are the same or different.

In the formula (34), Y 32 , Y 34 and Y 36 are each independently preferably CR 31 , in which a plurality of R 31 are the same or different.

The substituted germanium group is preferably represented by —Ge(R 301 ) 3 . R 301 is each independently a substituent. The substituent R 301 is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. A plurality of R 301 are mutually the same or different.

The partial structure represented by the formula (32) is preferably included in the third compound as at least one group selected from the group consisting of groups represented by formulae (35) to (39) and a group represented by a formula (30a).

In the formula (35), Y 41 to Y 48 are each independently a nitrogen atom or CR 32 .

In the formulae (36) and (37), Y 41 to Y 45 , Y 47 and Y 48 are each independently a nitrogen atom or CR 32 .

In the formula (38), Y 41 , Y 42 , Y 44 , Y 45 , Y 47 and Y 48 are each independently a nitrogen atom or CR 32 .

In the formula (39), Y 42 to Y 48 are each independently a nitrogen atom or CR 32 .

In the formula (30a), Y 42 to Y 47 are each independently a nitrogen atom or CR 32 .

In the formulae (35) to (39) and (30a), R 32 each independently represents a hydrogen atom or a substituent.

R 32 as the substituent is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted germanium group, a substituted phosphine oxide group, a halogen atom, a cyano group, a nitro group, and a substituted or unsubstituted carboxy group.

A plurality of R 32 are the same or different.

In the formulae (37) to (39) and (30a), X 30 is NR 33 , an oxygen atom or a sulfur atom.

R 33 is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted germanium group, a substituted phosphine oxide group, a fluorine atom, a cyano group, a nitro group, and a substituted or unsubstituted carboxy group.

A plurality of R 33 are the same or different.

The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms for R 33 is preferably a non-fused ring.

The mark * in the formulae (35) to (39) and (30a) each independently shows a bonding position with another atom or another structure in the molecule of the third compound.

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In the formula (35), Y 41 to Y 48 are each independently preferably CR 32 . In the formulae (36) and (37), Y 41 to Y 45 , Y 47 and Y 48 are each independently preferably CR 32 . In the formula (38), Y 41 , Y 42 , Y 44 , Y 45 , Y 47 and Y 48 are each independently preferably CR 32 . In the formula (39), Y 42 to Y 48 are each independently preferably CR 32 . In the formula (30a), Y 42 to Y 47 are each independently preferably CR 32 . A plurality of R 32 are the same or different.

In the third compound, X 30 is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.

In the third compound, R 31 and R 32 each independently represent a hydrogen atom or a substituent. R 31 and R 32 as the substituents are preferably each independently a group selected from the group consisting of a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. R 31 and R 32 are more preferably a hydrogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. When R 31 and R 32 as the substituents are each a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, the aryl group is preferably a non-fused ring.

It is also preferable that the third compound is an aromatic hydrocarbon compound or an aromatic heterocyclic compound.

Manufacturing Method of Third Compound

The third compound can be manufactured by methods disclosed in International Publication No. WO2012/153780, International Publication No. WO2013/038650, and the like. Furthermore, the second compound can be manufactured, for instance, by application of known substitution reactions and/or materials depending on a target compound.

Examples of the substituent in the third compound are shown below, but the invention is not limited thereto.

Specific examples of the aryl group (occasionally referred to as an aromatic hydrocarbon) group) include a phenyl group, tolyl group, xylyl group, naphthyl group, phenanthryl group, pyrenyl group, chrysenyl group, benzo[c]phenanthryl group, benzo[g]chrysenyl group, benzoanthryl group, triphenylenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, biphenyl group, terphenyl group, quarterphenyl group and fluoranthenyl group, among which a phenyl group, biphenyl group, terphenyl group, quarterphenyl group, naphthyl group, triphenylenyl group and fluorenyl group may be preferable.

Specific examples of the aryl group having a substituent include a tolyl group, xylyl group and 9,9-dimethylfluorenyl group.

As is understood from the specific examples, the aryl group includes both fused aryl group and non-fused aryl group.

Preferable examples of the aryl group include a phenyl group, biphenyl group, terphenyl group, quarterphenyl group, naphthyl group, triphenylenyl group and fluorenyl group.

Specific examples of the heteroaryl group (occasionally referred to as a heterocyclic group, heteroaromatic ring group or aromatic heterocyclic group) include a pyrrolyl group, pyrazolyl group, pyrazinyl group, pyrimidinyl group, pyridazynyl group, pyridyl group, triazinyl group, indolyl group, isoindolyl group, imidazolyl group, benzimidazolyl group, indazolyl group, imidazo[1,2-a]pyridinyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzofuranyl group, thiophenyl group, benzothienyl group, dibenzothienyl group, azadibenzothienyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, naphthyridinyl group, carbazolyl group, azacarbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, oxazolyl group, oxadiazolyl group, furazanyl group, benzoxazolyl group, thienyl group, thiazolyl group, thiadiazolyl group, benzothiazolyl group, triazolyl group and tetrazolyl group, among which a dibenzofuranyl group, dibenzothienyl group, carbazolyl group, pyridyl group, pyrimidinyl group, triazinyl group, azadibenzofuranyl group and azadibenzothienyl group may be preferable.

The heteroaryl group is preferably a dibenzofuranyl group, dibenzothienyl group, carbazolyl group, pyridyl group, pyrimidinyl group, triazinyl group, azadibenzofuranyl group or azadibenzothienyl group, and more preferably a dibenzofuranyl group, dibenzothienyl group, azadibenzofuranyl group and azadibenzothienyl group.

In the third compound, it is also preferable that the substituted silyl group is selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, or a substituted or unsubstituted triarylsilyl group.

Specific examples of the substituted or unsubstituted trialkylsilyl group include trimethylsilyl group and triethylsilyl group.

Specific examples of the substituted or unsubstituted arylalkylsilyl group include diphenylmethylsilyl group, ditolylmethylsilyl group, and phenyldimethylsilyl group.

Specific examples of the substituted or unsubstituted triarylsilyl group include triphenylsilyl group and tritolylsilyl group.

In the third compound, it is also preferable that the substituted phosphine oxide group is a substituted or unsubstituted diaryl phosphine oxide group.

Specific examples of the substituted or unsubstituted diaryl phosphine oxide group include a diphenyl phosphine oxide group and ditolyl phosphine oxide group.

In the third compound, the substituted carboxy group is exemplified by a benzoyloxy group.

Specific examples of the third compound in the exemplary embodiment are shown below. It should be noted that the third compound of the invention is not limited to the specific examples.

Relationship Between First Compound, Second Compound and Third Compound in Emitting Layer

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In the organic EL device of the exemplary embodiment, the singlet energy S1(Mat1) of the first compound and a singlet energy S1(Mat3) of the third compound preferably satisfies a relationship of Numerical Formula 2 below.

S 1 (Mat3)> S 1 (Mat1) (Numerical Formula 2)

The energy gap T 77K (Mat3) at 77 [K] of the third compound is preferably larger than an energy gap T 77K (Mat1) at 77 [K] of the first compound.

The energy gap T 77K (Mat3) at 77 [K] of the third compound is preferably larger than the energy gap T 77K (Mat2) at 77 [K] of the second compound

The singlet energy S 1 (Mat1) of the first compound, the singlet energy S 1 (Mat2) of the second compound, the singlet energy S 1 (Mat3) of the third compound preferably satisfy a relationship of Numerical Formula 2A.

S 1 (Mat3)> S 1 (Mat1)> S 1 (Mat2) (Numerical Formula 2A)

The energy gap T 77K (Mat1) at 77[K] of the first compound, the energy gap T 77K (Mat2) at 77[K] of the second compound, and the energy gap T 77K (Mat3) at 77[K] of the third compound preferably satisfy a relationship of Numerical Formula 2B.

T 77K (Mat3)> T 77K (Mat1)> T 77K (Mat2) (Numerical Formula 2B)

When the organic EL device of the exemplary embodiment emits light, it is preferable that the fluorescent compound in the emitting layer mainly emits light.

The organic EL device of the fourth exemplary embodiment preferably emits red light or green light in the same manner as the organic EL device of the third exemplary embodiment.

A main peak wavelength of the organic EL device can be measured by the same method as that for the organic EL device of the third exemplary embodiment.

Content Ratio of Compounds in Emitting Layer

Content ratios of the first, second and third compounds in the emitting layer are, for instance, preferably determined as follows.

The content ratio of the third compound is preferably in a range from 10 mass % to 80 mass %.

An upper limit of the total of the respective content ratios of the first, second and third compounds in the emitting layer is 100 mass %. It should be noted that the emitting layer of the exemplary embodiment may further contain material(s) other than the first, second and third compounds.

The emitting layer may include a single type of the first compound or may include two or more types of the first compound. The emitting layer may include a single of the second compound or may include two or more types of the second compound. The emitting layer may include a single of the third compound or may include two or more types of the third compound.

FIG. 5 shows an example of a relationship between energy levels of the first, second and third compounds in the emitting layer. In FIG. 5 , S0 represents a ground state. S1(Mat1) represents the lowest singlet state of the first compound. T1(Mat1) represents the lowest triplet state of the first compound. S1(Mat2) represents the lowest singlet state of the second compound. T1(Mat2) represents the lowest triplet state of the second compound. S1(Mat3) represents the lowest singlet state of the third compound. T1(Mat3) represents the lowest triplet state of the third compound. A dashed arrow directed from S1(Mat1) to S1(Mat2) in FIG. 5 represents Förster energy transfer from the lowest singlet state of the first compound to the lowest singlet state of the fluorescent compound.

As shown in FIG. 5 , when a compound having a small ΔST(Mat1) is used as the first compound, inverse intersystem crossing from the lowest triplet state T1(Mat1) to the lowest singlet state S1(Mat1) can be caused by a heat energy. Subsequently, Förster energy transfer from the lowest singlet state S1(Mat1) of the first compound the second compound occurs to generate the lowest singlet state S1(Mat2). Consequently, fluorescence from the lowest singlet state S1(Mat2) of the second compound can be observed. It is inferred that the internal quantum efficiency can be theoretically raised up to 100% also by using delayed fluorescence by the TADF mechanism.

The organic EL device 1 according to the fourth exemplary embodiment contains the first compound that is the compound according to the first exemplary embodiment (at least one of the compounds represented by the formulae (11) to (13)), the second compound having the singlet energy smaller than that of the first compound in the emitting layer 5 , and the third compound having the singlet energy larger than that of the first compound.

The organic EL device according to the fourth exemplary embodiment is applicable to an electronic device such as a display device and a light-emitting device.

Fifth Exemplary Embodiment

An arrangement of an organic EL device according to a fifth exemplary embodiment will be described below. In the description of the fifth exemplary embodiment, the same components as those in the third and fourth exemplary embodiments are denoted by the same reference signs and names to simplify or omit an explanation of the components. In the fifth exemplary embodiment, any materials and compounds that are not specified may be the same as those in the third and fourth exemplary embodiments.

The organic EL device according to the fifth exemplary embodiment is different from the organic EL device according to the third exemplary embodiment in that the emitting layer further includes a fourth compound in place of the second compound. The rest of the arrangement of the organic EL device according to the fifth exemplary embodiment is the same as in the third exemplary embodiment.

In the fifth exemplary embodiment, the emitting layer contains the first compound and the fourth compound.

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In the fifth exemplary embodiment, the first compound is preferably a dopant material (occasionally referred to as a guest material, emitter or luminescent material) and the fourth compound is preferably a host material (occasionally referred to as a matrix material).

The fourth compound may be a thermally activated delayed fluorescent compound or a compound exhibiting no thermally activated delayed fluorescence.

Although the fourth compound is not particularly limited, for instance, the third compound described in the fourth exemplary embodiment is usable as the fourth compound.

Relationship between First Compound and Fourth Compound in Emitting Layer

In the organic EL device of the exemplary embodiment, the singlet energy S 1 (Mat1) of the first compound and a singlet energy S 1 (Mat4) of the fourth compound preferably satisfies a relationship of Numerical Formula 4 below.

S 1 (Mat4)> S 1 (Mat1) (Numerical Formula 4)

An energy gap T 77K (Mat4) at 77 [K] of the fourth compound is preferably larger than the energy gap T 77K (Mat1) at 77 [K] of the first compound. In other words, a relationship of Numerical Formula 4A is preferably satisfied.

T 77K (Mat4)> T 77K (Mat1) (Numerical Formula 4A)

When the organic EL device of the exemplary embodiment emits light, it is preferable that the first compound in the emitting layer mainly emits light.

Content Ratios of Compounds in Emitting Layer

Content ratios of the first and fourth compounds in the emitting layer are, for instance, preferably determined as follows.

The content ratio of the fourth compound is preferably in a range from 20 mass % to 90 mass %, more preferably in a range from 40 mass % to 90 mass %, further preferably in a range from 40 mass % to 80 mass %.

It should be noted that the emitting layer of the exemplary embodiment may further contain material(s) other than the first and fourth compounds.

The emitting layer may include a single type of the first compound or may include two or more types of the first compound. The emitting layer may include a single type of the fourth compound or may include two or more types of the fourth compound.

FIG. 6 shows an example of a relationship between energy levels of the first and fourth compounds in the emitting layer. In FIG. 6 , S0 represents a ground state. S 1 (Mat1) represents the lowest singlet state of the first compound. T1(Mat1) represents the lowest triplet state of the first compound. S 1 (Mat4) represents the lowest singlet state of the fourth compound. T1(Mat4) represents the lowest triplet state of the fourth compound. Dashed arrows in FIG. 6 represent energy transfer from the fourth compound to the first compound in the lowest singlet state and in the lowest triplet state, respectively. An energy transfer occurs by Förster transfer from the lowest singlet state S 1 of the fourth compound to the lowest singlet state S 1 of the first compound or an energy transfer occurs by Dexter transfer from the lowest triplet state T1 of the fourth compound to the lowest triplet state T1 of the first compound. Further, when a material having a small ΔST(Mat1) is used as the first compound, inverse intersystem crossing can be caused by a heat energy from the lowest triplet state T1 to the lowest singlet state S 1 in the first compound. Consequently, fluorescence from the lowest singlet state S 1 of the first compound can be observed. It is inferred that the internal quantum efficiency can be theoretically raised up to 100% also by using delayed fluorescence by the TADF mechanism.

The organic EL device according to the fifth exemplary embodiment contains the first compound that is the compound according to the first exemplary embodiment (at least one of the compounds represented by the formulae (11) to (13)), and the fourth compound having the singlet energy larger than that of the first compound in the emitting layer.

The organic EL device according to the fifth exemplary embodiment is applicable to an electronic device such as a display device and a light-emitting device.

Sixth Exemplary Embodiment

Electronic Device

An electronic device according to a sixth exemplary embodiment is installed with one of the organic EL devices according to the above exemplary embodiments. Examples of the electronic device include a display device and a light-emitting unit. Examples of the display device include a display component (e.g., an organic EL panel module), TV, mobile phone, tablet and personal computer. Examples of the light-emitting unit include an illuminator and a vehicle light.

Modification of Embodiment(s)

It should be noted that the invention is not limited to the above exemplary embodiments but may include any modification and improvement as long as such modification and improvement are compatible with the invention.

For instance, the emitting layer is not limited to a single layer, but may be provided by laminating a plurality of emitting layers. When the organic EL device has a plurality of emitting layers, it is only required that at least one of the emitting layers satisfies the conditions described in the above exemplary embodiments. For instance, in some embodiments, the rest of the emitting layers is a fluorescent emitting layer or a phosphorescent emitting layer with use of emission caused by electron transfer from the triplet excited state directly to the ground state.

When the organic EL device includes the plurality of emitting layers, in some embodiments, the plurality of emitting layers are adjacent to each other, or provide a so-called tandem-type organic EL device in which a plurality of emitting units are layered through an intermediate layer.

For instance, in some embodiments, a blocking layer is provided adjacent to at least one side of a side near the anode and a side near the cathode of the emitting layer. The blocking layer is preferably provided in contact with the emitting layer to at least block holes, electrons or excitons.

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For instance, when the blocking layer is provided in contact with the cathode-side of the emitting layer, the blocking layer permits transport of electrons, but blocks holes from reaching a layer provided near the cathode (e.g., the electron transporting layer) beyond the blocking layer. When the organic EL device includes the electron transporting layer, the organic EL device preferably includes the blocking layer between the emitting layer and the electron transporting layer.

When the blocking layer is provided in contact with the anode-side of the emitting layer, the blocking layer permits transport of holes, but blocks electrons from reaching a layer provided near the anode (e.g., the hole transporting layer) beyond the blocking layer. When the organic EL device includes the hole transporting layer, the organic EL device preferably includes the blocking layer between the emitting layer and the hole transporting layer.

Moreover, for instance, in some embodiments, the blocking layer abuts on the emitting layer so that excited energy does not leak out from the emitting layer toward neighboring layer(s). The blocking layer blocks excitons generated in the emitting layer from transferring to a layer(s) (e.g., the electron transporting layer and the hole transporting layer) closer to the electrode(s) beyond the blocking layer.

The emitting layer and the blocking layer are preferably bonded with each other.

Specific structure and shape of the components in the invention may be designed in any manner as long as the object of the invention can be achieved.

Herein, numerical ranges represented by “x to y” represents a range whose lower limit is the value (x) recited before “to” and whose upper limit is the value (y) recited after “to.”

Rx and Ry are mutually bonded to form a ring, which means herein, for instance, that Rx and Ry contain a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a silicon atom, the atom (a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a silicon atom) contained in Rx and the atom (a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a silicon atom) contained in Ry are mutually bonded via a single bond, a double bond, a triple bond or a divalent linking group to form a ring having 5 or more ring atoms (specifically, a heterocyclic ring or an aromatic hydrocarbon ring). x represents a number, a character or a combination of a number and a character. y represents a number, a character or a combination of a number and a character.

The divalent linking group is not particularly limited and is exemplified by —O—, —CO—, —CO 2 —, —S—, —SO—, —SO 2 —, —NH—, —NRa—, and a group obtained by combining two or more linking groups of those.

Specific examples of the heterocyclic ring include a cyclic structure (heterocyclic ring) obtained by removing a bond from a “heteroaryl group” exemplarily shown in the later-described “Description of Each Substituent in Formula.” The heterocyclic ring may have a substituent.

Specific examples of the aromatic hydrocarbon ring include a cyclic structure (aromatic hydrocarbon ring) obtained by removing a bond from an “aryl group” exemplarily shown in the later-described “Description of Each Substituent in Formula.” The aromatic hydrocarbon ring may have a substituent.

Examples of Ra include a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

Rx and Ry are mutually bonded to form a ring, which means, for instance, that an atom contained in Rx 1 and an atom contained in Ry 1 in a molecular structure represented by a formula (E1) below form a ring (cyclic structure) E represented by a formula (E2); that an atom contained in Rx 1 and an atom contained in Ry 1 in a molecular structure represented by a formula (F1) below form a ring (cyclic structure) F represented by a formula (F2); that an atom contained in Rx 1 and an atom contained in Ry 1 in a molecular structure represented by a formula (G1) below form a ring (cyclic structure) G represented by a formula (G2); that an atom contained in Rx 1 and an atom contained in Ry 1 in a molecular structure represented by a formula (H1) below form a ring (cyclic structure) H represented by a formula (H2); and that an atom contained in Rx 1 and an atom contained in Ry 1 in a molecular structure represented by a formula (I1) below form a ring (cyclic structure) I represented by a formula (I2).

In the formulae (E1) to (I1), * each independently represents a bonding position to another atom in a molecule. Two * in the formula (E1) correspond one-to-one to two * in the formula (E2). Two * in the formula (F1) correspond one-to-one to two in the formula (F2). Two * in the formula (G1) correspond one-to-one to two in the formula (G2). Two * in the formula (H1) correspond one-to-one to two * in the formula (H2). Two * in the formula (I1) correspond one-to-one to two * in the formula (I2).

In the molecular structures represented by the respective formulae (E2) to (I2), E to I each represent a cyclic structure (the ring having 5 or more ring atoms). In the formulae (E2) to (I2), * each independently represents a bonding position to another atom in a molecule. Two * in the formula (E2) correspond one-to-one to two * in the formula (E1). Similarly, two * in each of the formulae (F2) to (I2) correspond one-to-one to two * in in each of the formulae (F1) to (I1).

For instance, in the formula (E1), Rx 1 and Ry 1 are mutually bonded to for the ring E in the formula (E2) and the ring E is an unsubstituted benzene ring, the molecular structure represented by the formula (E1) is a molecular structure represented by a formula (E3) below. Herein, two * in the formula (E3) each independently correspond to two * in the formula (E2) and the formula (E1).

For instance, in the formula (E1), Rx 1 and Ry 1 are mutually bonded to for the ring E in the formula (E2) and the ring E is an unsubstituted pyrrole ring, the molecular structure represented by the formula (E1) is a molecular structure represented by a formula (E4) below. Herein, two * in the formula (E4) each independently correspond to two * in the formula (E2) and the formula (E1). In the formulae (E3) and (E4), * each independently represents a bonding position to another atom in a molecule.

›MEANS FOR SOLVING THE PROBLEMS · 21 of 23

Herein, the ring carbon atoms refer to the number of carbon atoms among atoms forming a ring of a compound (e.g., a monocyclic compound, fused-ring compound, crosslinking compound, carbon ring compound, and heterocyclic compound) in which the atoms are bonded to each other to form the ring. When the ring is substituted by a substituent(s), carbon atom(s) contained in the substituent(s) is not counted in the ring carbon atoms. Unless specifically described, the same applies to the “ring carbon atoms” described later. For instance, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridinyl group has 5 ring carbon atoms, and a furanyl group has 4 ring carbon atoms. When a benzene ring and/or a naphthalene ring is substituted by a substituent (e.g., an alkyl group), the number of carbon atoms of the alkyl group is not counted in the number of the ring carbon atoms. When a fluorene ring is substituted by a substituent (e.g., a fluorene ring) (i.e., a spirofluorene ring is included), the number of carbon atoms of the fluorene ring as the substituent is not counted in the number of the ring carbon atoms of the fluorene ring.

Herein, the ring atoms refer to the number of atoms forming a ring of a compound (e.g., a monocyclic compound, fused-ring compound, crosslinking compound, carbon ring compound, and heterocyclic compound) in which the atoms are bonded to each other to form the ring (e.g., monocyclic ring, fused ring, ring assembly). Atom(s) not forming a ring and atom(s) included in a substituent when the ring is substituted by the substituent are not counted in the number of the ring atoms. Unless specifically described, the same applies to the “ring atoms” described later. For instance, a pyridine ring has six ring atoms, a quinazoline ring has ten ring atoms, and a furan ring has five ring atoms. A hydrogen atom(s) and/or an atom(s) of a substituent which are bonded to carbon atoms of a pyridine ring and/or quinazoline ring are not counted in the ring atoms. When a fluorene ring is substituted by a substituent (e.g., a fluorene ring) (i.e., a spirofluorene ring is included), the number of atoms of the fluorene ring as the substituent is not counted in the number of the ring atoms of the fluorene ring.

Description of Each Substituent in Formula Herein

Examples of the aryl group (occasionally referred to as an aromatic hydrocarbon group) herein include a phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, fluorenyl group, pyrenyl group, chrysenyl group, fluoranthenyl group, benz[a]anthryl group, benzo[c]phenanthryl group, triphenylenyl group, benzo[k]fluoranthenyl group, benzo[g]chrysenyl group, benzo[b]triphenylenyl group, picenyl group, and perylenyl group.

Herein, the aryl group preferably has 6 to 20 ring carbon atoms, more preferably 6 to 14 ring carbon atoms, further preferably 6 to 12 ring carbon atoms. Among the aryl group, a phenyl group, biphenyl group, naphthyl group, phenanthryl group, terphenyl group and fluorenyl group are preferable. A carbon atom in a position 9 of each of 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group and 4-fluorenyl group is preferably substituted by a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group described later herein.

The heteroaryl group (occasionally referred to as heterocyclic group, heteroaromatic ring group or aromatic heterocyclic group) herein preferably contains as a hetero atom, at least one atom selected from the group consisting of nitrogen, sulfur, oxygen, silicon, selenium atom and germanium atom, and more preferably contains at least one atom selected from the group consisting of nitrogen, sulfur and oxygen.

Examples of the heterocyclic group hereint are a pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyridinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl group, imidazopyridinyl group, benzotriazolyl group, carbazolyl group, furyl group, thienyl group, oxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, benzofuranyl group, benzothienyl group, benzoxazolyl group, benzothiazolyl group, benzisoxazolyl group, benzisothiazolyl group, benzoxadiazolyl group, benzothiadiazolyl group, dibenzofuranyl group, dibenzothienyl group, piperidinyl group, pyrrolidinyl group, piperazinyl group, morpholyl group, phenazinyl group, phenothiazinyl group, and phenoxazinyl group.

Herein, the heterocyclic group preferably has 5 to 20 ring carbon atoms, more preferably 5 to 14 ring carbon atoms. Among the above heterocyclic group, a 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothienyl group, 2-dibenzothienyl group, 3-dibenzothienyl group, 4-dibenzothienyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, and 9-carbazolyl group are further preferable. A nitrogen atom in position 9 of 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group and 4-carbazolyl group is preferably substituted by the substituted or unsubstituted aryl group or the substituted or unsubstituted heterocyclic group described herein.

Herein, the heterocyclic group may be a group derived from any one of moieties represented by formulae (XY-1) to (XY-18) below.

In the formulae (XY-1) to (XY-18), XA and YA each independently represent a hetero atom, and preferably represent an oxygen atom, sulfur atom, selenium atom, silicon atom or germanium atom. Each of the moieties represented by the respective formulae (XY-1) to (XY-18) has a bond at any position to provide a heterocyclic group. The heterocyclic group may be substituted.

Examples of a substituted or unsubstituted carbazolyl group herein may contain groups represented by formulae (XY-19) to (XY-22) in which a further group is fused to a carbazole ring. The groups each may have a substituent. Moreover, the position of the bond may be changed as needed

›MEANS FOR SOLVING THE PROBLEMS · 22 of 23

The alkyl group herein may be linear, branched or cyclic. Also, the alkyl group may be an alkyl halide group.

Examples of the linear or branched alkyl group include: a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, amyl group, isoamyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, and 3-methylpentyl group.

Herein, the linear or branched alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. As the linear or branched alkyl group, a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, amyl group, isoamyl group and neopentyl group are further more preferable.

Herein, examples of the cyclic alkyl group include a cycloalkyl group.

Examples of the cycloalkyl group herein are a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-metylcyclohexyl group, adamantyl group and norbornyl group. The cycloalkyl group preferably has 3 to 10 ring carbon atoms, more preferably 5 to 8 ring carbon atoms. Among the cycloalkyl group, a cyclopentyl group and a cyclohexyl group are further more preferable.

Herein, the alkyl halide group provided by substituting the alkyl group with a halogen atom is exemplified by an alkyl halide group provided by substituting the alkyl group with at least one halogen atom, preferably at least one fluorine atom.

Herein, examples of the alkyl halide group include a fluoromethyl group, difluoromethyl group, trifluoromethyl group, fluoroethyl group, trifluoromethylmethyl group, trifluoroethyl group, and pentafluoroethyl group.

Herein, examples of a substituted silyl group include an alkylsilyl group and an arylsilyl group.

Herein, the alkylsilyl group is exemplified by a trialkylsilyl group having the above examples of the alkyl group. Specific examples of the alkylsilyl group are a trimethylsilyl group, triethylsilyl group, tri-n-butylsilyl group, tri-n-octylsilyl group, triisobutylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group, dimethyl-n-propylsilyl group, dimethyl-n-butylsilyl group, dimethyl-t-butylsilyl group, diethylisopropylsilyl group, vinyl dimethylsilyl group, propyldimethylsilyl group, and triisopropylsilyl group. Three alkyl groups in the trialkylsilyl group may be mutually the same or different.

Herein, examples of the arylsilyl group include a dialkylarylsilyl group, alkyldiarylsilyl group and triarylsilyl group.

The dialkylarylsilyl group is exemplified by a dialkylarylsilyl group including two of the alkyl groups listed as the examples of the alkyl group and one of the aryl groups listed as the examples of the aryl group. The dialkylarylsilyl group preferably has 8 to 30 carbon atoms.

The alkyldiarylsilyl group is exemplified by an alkyldiarylsilyl group including one of the alkyl groups listed as the examples of the alkyl group and two of the aryl groups listed as the examples of the aryl group. The alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.

The triarylsilyl group is exemplified by a triarylsilyl group including three of the aryl group listed as the above examples of the aryl group. The triarylsilyl group preferably has 18 to 30 carbon atoms.

Herein, the alkyl sulfonyl group is represented by —SO 2 R w , where R w represents a substituted or unsubstituted alkyl group.

Examples of the substituted or unsubstituted alkylsulfonyl group herein include a group represented by the above —SO 2 R w , where R w is substituted or unsubstituted alkyl group.

Herein, an aryl group in an aralkyl group (occasionally referred to as an arylalkyl group) is an aromatic hydrocarbon group or a heterocyclic group.

The aralkyl group herein is preferably a group having an aryl group and is represented by —Z 3 -Z 4 . Z 3 is exemplified by an alkylene group corresponding to the above alkyl group. Z 4 is exemplified by the above aryl group. In this aralkyl group, an aryl moiety has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms and an alkyl moiety has 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1 to 6 carbon atoms. Examples of the aralkyl group are a benzyl group, 2-phenylpropane-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

The alkoxy group herein is represented by —OZ 1 . Z 1 is exemplified by the above alkyl group. Examples of the alkoxy group include a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group and hexyloxy group. Thealkoxy group preferably has 1 to 20 carbon atoms.

A halogenated alkoxy group provided by substituting an alkoxy group with a halogen atom is exemplified by one provided by substituting an alkoxy group with one or more fluorine atoms.

Herein, an aryl group in an aryloxy group (sometime referred to as an arylalkoxy group) also includes a heteroaryl group.

The arylalkoxy group herein is represented by —OZ 2 . Z 2 is exemplified by the above aryl group. The arylalkoxy group preferably has 6 to 20 ring carbon atoms. The arylalkoxy group is exemplified by a phenoxy group.

Herein, the substituted amino group is represented by —NHRV or —N(RV)2. R V is exemplified by the above alkyl group and aryl group.

Herein, the alkenyl group is linear or branched. Examples of the alkenyl group include a vinyl group, propenyl group, butenyl group, oleyl group, eicosapentaenyl group, docosahexaenyl group, styryl group, 2,2-diphenylvinyl group, 1,2,2-triphenylvinyl group, and 2-phenyl-2-propenyl group.

›MEANS FOR SOLVING THE PROBLEMS · 23 of 23

The alkynyl group herein may be linear or branched. Examples of the alkynyl group are an ethynyl group, a propynyl group and a 2-phenylethynyl group.

Herein, the alkylthio group and the arylthio group are represented by —SR V . R V is exemplified by the above alkyl group and aryl group. The alkylthio group preferably has 1 to 20 carbon atoms. The arylthio group preferably has 6 to 20 ring carbon atoms.

Herein, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, among which a fluorine atom is preferable.

Herein, examples of a substituted phosphino group include a phenyl phosphanyl group.

The arylcarbonyl group herein is represented by —COY′. Y′ is exemplified by the above aryl group. Examples of the arylcarbonyl group herein include a phenyl carbonyl group, diphenyl carbonyl group, naphthyl carbonyl group, and triphenyl carbonyl group.

The acyl group herein is represented by —COR′. R′ is exemplified by the above alkyl group. Herein, examples of the acyl group include an acetyl group and a propionyl group.

A substituted phosphoryl group herein is represented by a formula (P).

In the formula (P), Ar P1 and Ar P2 are each a substituent selected from the group consisting of the above alkyl group and the above aryl group.

Herein, examples of an ester group include an alkyl ester group. The alkyl ester group is represented by —C(═O)OR E . R E is exemplified by a substituted or unsubstituted alkyl group. The alkyl group is exemplified by the above “alkyl group herein.”

A siloxanyl group herein is a silicon compound group via an ether bond, examples of which include a trimethylsiloxanyl group.

Herein, “carbon atoms forming a ring (ring carbon atoms)” mean carbon atoms forming a saturated ring, unsaturated ring, or aromatic ring. “Atoms forming a ring (ring atoms)” mean carbon atoms and hetero atoms forming a ring including a saturated ring, unsaturated ring, or aromatic ring.

Herein, a hydrogen atom includes isotope having different numbers of neutrons, specifically, protium, deuterium and tritium.

Herein, the substituent meant by “substituted or unsubstituted” is at least one group selected from the group consisting of an aryl group, heteroaryl group, linear alkyl group, branched alkyl group, cycloalkyl group, alkyl halide group, substituted or unsubstituted silyl group (e.g., alkylsilyl group, arylsilyl group), alkoxy group, alkoxy halide group, aryloxy group, substituted or unsubstituted amino group, alkylthio group, arylthio group, aralkyl group, alkenyl group, halogen atom, alkynyl group, cyano group, hydroxy group, nitro group, carboxy group and substituted phosphoryl group.

Herein, the substituent meant by “substituted or unsubstituted” is also exemplified by a diaryl boron group (Ar B1 Ar B2 B—). Ar B1 and Ar B2 are exemplified by the above aryl group.

Examples of the substituent meant by “substituted or unsubstituted” and preferable ones of the examples thereof are the same as the examples of the substituent and the preferable ones of the examples thereof in “Description of Each Substituent.”

The substituent meant by “substituted or unsubstituted” may be further substituted by at least one group selected from the group consisting of an aryl group, heteroaryl group, linear alkyl group, branched alkyl group, cycloalkyl group, alkyl halide group, alkylsilyl group, arylsilyl group, alkoxy group, alkoxy halide group, aryloxy group, substituted or unsubstituted amino group, alkylthio group, arylthio group, aralkyl group, alkenyl group, alkynyl group, halogen atom, cyano group, hydroxy group, nitro group, and carboxy group. In addition, adjacent two or more of the substituents may be bonded to each other to form a ring.

The substituent meant by “substituted or unsubstituted” may be further substituted by an acyl group.

“Unsubstituted” in “substituted or unsubstituted” means that a group is not substituted by the above-described substituents but bonded with a hydrogen atom.

Herein, “XX to YY carbon atoms” in the description of “substituted or unsubstituted ZZ group having XX to YY carbon atoms” represent carbon atoms of an unsubstituted ZZ group and do not include carbon atoms of a substituent(s) of the substituted ZZ group.

Herein, “XX to YY atoms” in the description of “substituted or unsubstituted ZZ group having XX to YY atoms” represent atoms of an unsubstituted ZZ group and does not include atoms of a substituent(s) of the substituted ZZ group.

The same description as the above applies to “substituted or unsubstituted” in compounds or moieties thereof described herein.

Herein, when the substituents are bonded to each other to form a ring, the ring is structured to be a saturated ring, an unsaturated ring, an aromatic hydrocarbon ring or a hetero ring.

Herein, examples of the aromatic hydrocarbon group and the heterocyclic group in the linking group include a divalent or multivalent group obtained by eliminating one or more atoms from the above monovalent groups.

›EXAMPLES

Example(s) of the invention will be described below. However, the invention is not limited to Example(s).

Compounds used in Examples and Comparatives will be shown below.

(1) Synthesis Example 1: Synthesis of Compound TADF1

(1-1) Synthesis of Intermediate A

Under nitrogen atmosphere, 2M sodium carbonate aqueous solution (124 mL, 248 mmol), 1,2-dimethoxyethane (DME) (250 mL), toluene (250 mL), and tetrakis(triphenylphosphine)palladium(0) (Pd[PPh 3 ] 4 ) (7.2 g, 6.2 mmol) were added to 2-bromonitrobenzene (25.0 g, 123.8 mmol) and 4-dibenzofuran boronic acid (31.5 g, 148.5 mmol) and the obtained mixture was heated to reflux with stirring for 12 hours. After the reaction, the mixture was cooled to the room temperature (25 degrees C.). A sample was transferred to a separating funnel, added with water (500 mL), and extracted with dichloromethane. The extracted sample was dried over MgSO 4 , filtered and condensed. The obtained sample was purified by silica-gel column chromatography to obtain a white solid (24.0 g). The solid was identified as an intermediate A by analysis according to FD-MS (Field Desorption Mass Spectrometry) (a yield rate: 67%).

(1-2) Synthesis of Intermediate B

Under argon atmosphere, dimethylacetamide (DMAC) (166 mL) was added to the intermediate A (24.0 g, 83.0 mmol) and triphenylphosphine (PPh 3 ) (54.4 g, 207.4 mmol) and the obtained mixture was heated to reflux with stirring for 20 hours. After the reaction, the mixture was cooled to the room temperature (25 degrees C.). A sample was transferred to a separating funnel, added with water (400 mL), and extracted with dichloromethane. The extracted sample was dried over MgSO 4 , filtered and condensed. The obtained sample was purified by silica-gel column chromatography to obtain a white solid (14.5 g). The solid was identified as an intermediate B by analysis according to FD-MS (a yield rate: 68%).

(1-3) Synthesis of Intermediate C

Under nitrogen atmosphere, to a 50-mL Schlenk tube, carbazole (2.0 g, 12 mmol), potassium carbonate (3.3 g, 24 mmol), tetrafluoroterephthalonitrile (4.8 g, 24 mmol), and N,N-dimethyl formamide (DMF) (20 mL) were added and stirred at the room temperature (25 degrees C.). After eight hours, water (200 mL) was added to the mixture. The deposited solid was purified by silica-gel column chromatography to obtain an orange solid (1.95 g). The solid was identified as an intermediate C by analysis according to ASAP-MS (Atmospheric Pressure Solid Analysis Probe Mass Spectrometry) and 1 H-NMR (a yield rate: 66%). In the scheme, “r.t,” represents the room temperature.

(1-4) Synthesis of TADF1

Under nitrogen atmosphere, to a 50-mL Schlenk tube, the intermediate C (0.57 g, 2.2 mmol), potassium carbonate (0.62 g, 4.4 mmol), the intermediate B (0.5 g, 1.0 mmol), and DMF (10 mL) were added and stirred at 60 degrees C. for six hours. After the reaction, the mixture was cooled to the room temperature (25 degrees C.). Water (200 mL) was added to the mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (0.75 g). The solid was identified as TADF1 by analysis according to ASAP-MS and 1 H-NMR (a yield rate: 77%).

›Examples49

›Example 1a · 1 of 2

The same compound TADF1 as that in Example 1 was prepared according to the following method. The compound TADF1 prepared in Example 1 was used for Evaluation of Compounds described later.

Synthesis of Intermediate a

Under nitrogen atmosphere, into a 500-mL eggplant flask, 1,4-dibromo-2,5-difluorobenzene (15.2 g, 55.9 mmol), copper chloride(I) (13.8 g, 139 mmol), and NMP (200 mL) were put and heated at 170 degrees C. with stirring. After four hours, the mixture was heated to 175 degrees C., further stirred for 1 hour, and then cooled to the room temperature (25 degrees C.). Water (200 mL) was added to the mixture. The deposited solid was removed by filtration through cerite. The filtrate was extracted with ethyl acetate. Subsequently, the obtained organic layer was washed with water and a saturated saline solution. After being dried over magnesium sulfate, the solvent was removed by a rotary evaporator under reduced pressure. The obtained compound was isolated and purified by silica-gel column chromatography to obtain 1,4-dichloro-2,5-difluorobenzene (intermediate a) (4.11 g, 22.5 mmol, a yield rate of 40%).

Synthesis of Intermediate b

Under nitrogen atmosphere, into a 200-mL three-necked flask, 1,4-dichloro-2,5-difluorobenzene (intermediate a) (4.11 g, 22.5 mmol), chlorotrimethylsilane (TMSCI) (6.3 mL, 50 mmol), and THF (25 mL) were put. The mixture was cooled to −78 degrees C. in a dry ice/aceton bath. Subsequently, lithium diisopropylamide (LDA), which was prepared, was all dropped into the mixture. The obtained solution was stirred for two hours at the room temperature (25 degrees C.). After added with water (10 mL), the solution was extracted with ethyl acetate. Subsequently, the obtained organic layer was washed with water and a saturated saline solution. After being dried over magnesium sulfate, the solvent was removed by a rotary evaporator under reduced pressure. The obtained 2,5-dichloro-3,6-difluoro-1,4-phenylenebistrimethylsilane (intermediate b) (6.61 g, 20.2 mmol) was not puried and used in a next reaction.

Synthesis of Intermediate c

Under nitrogen atmosphere, into a 500-mL eggplant flask, 2,5-dichloro-3,6-difluoro-1,4-phenylenebistrimethylsilane (intermediate b)(6.61 g, 20.2 mmol), and dichloromethane (DCM) (100 mL) were put. Iodine monochloride (2.5 mL) was dropped into the mixture at the room temperature (25 degrees C.) and subsequently stirred at 40 degrees C. Iodine monochloride (2.5 mL) was dropped into a reaction system every two hours, resulting in addition of the total amount of 4.5 mL of iodine monochoride. After all of iodine monochoride was dropped into the reactant mixture, the reactant mixture was further stirred for 1 hour and 30 minutes and returned to the room temperature (25 degrees C.). The reactant mixture was added with a saturated acueous solution of sodium thiosulfate (20 mL) and extracted with dichloromethane. Subsequently, the obtained organic layer was washed with water and a saturated saline solution. After being dried over magnesium sulfate, the solvent was removed by a rotary evaporator under reduced pressure. The obtained solution was purified by silica-gel column chromatography (eluent:hexane) to obtain 1,4-dichloro-2,5-difluoro-3,6-diiodobenzene (intermediate c) (6.20 g, 14.3 mmol, a yield rate of 71%).

Synthesis of Intermediate d

Into a 5-mL vial, 1,4-dichloro-2,5-difluoro-3,6-diiodobenzene (intermediate c) (435 mg, 1.0 mmol), copper cyanide (360 mg, 4.0 mmol), and DMF (5 mL) were put and heated at 150 degrees C. with stirring. After 1 hour and 30 minutes, the reaction solution was cooled to the room temperature (25 degrees C.) and poured into 10-mL ammonia water. After the reaction solution was extracted with methylene chloride, the obtained organic layer was washed with water and a saturated saline solution. After being dried over magnesium sulfate, the solvent was removed by a rotary evaporator under reduced pressure. The obtained solution was purified by silica-gel column chromatography (eluent:hexane/ethyl acetate=5/1 (volume ratio) to obtain 1,4-dicyano-2,5-dichloro-3,6-difluorobenzene (intermediate d) (0.16 g).

Synthesis of Intermediate e

Under nitrogen atmosphere; into a 50-mL eggplant flask, 1,4-dicyano-2,5-dichloro-3,6-difluorobenzene (intermediate d)(348 mg; 1.5 mmol), 9H-carbazole (501 mg, 3.0 mmol), potassium carbonate (415 mg, 3.0 mmol), and DMF (10 mL) were put and stirred at the room temperature (25 degrees C.). After 1 hour, water and methanol were each added at 3 mL to the mixture. The obtained mixture was extracted with methylene chloride. Subsequently, the obtained organic layer was washed with water and a saline solution; and dried over magnesium sulfate. The solvent was removed by a rotary evaporator under reduced pressure. The obtained compound was purified by silica-gel column chromatography to obtain 1,4-dicyano-25-di(9H-carbazolyl)-3,6-dichlorobenzene (intermediate e) (345 mg, 0.65 mmol, a yield rate of 44%). The obtained product (intermediate e) was identified in terms of a structure according to 1 H-NMR and LCMS (Liquid chromatography mass spectrometry).

Synthesis of TADF1

Into a 5-mL vial, 1,4-dicyano-2,5-di(9H-carbazolyl)-3,6-dichlorobenzene (intermediate e) (52 mg, 0.1 mmol), 5H-benzofuro[3,2-c]carbazole (intermediate B) (62 mg, 0.24 mmol), potassium carbonate (34 mg, 0.25 mmol), and DMF (2 mL) were put and heated with stirring at 60 degrees C. for 10 hours. After cooled to the room temperature (25 degrees C.), the reaction solution was purified by silica-gel column chromatography to obtain 1,4-dicyano-2,5-bis(5H-benzofuro[3,2-c]carbazole-5-yl)-3,6-di(9H-carbazolyl)benzene (TADF1) (27 mg, 0.028 mmol, a yield rate of 30%). The obtained product (TADF1) was identified in terms of a structure according to 1 H-NMR and LCMS.

Moreover, it was confirmed that the measurement result according to 1 H-NMR of the compound obtained by the method of Example 1a was in line with the measurement result according to 1 H-NMR of the compound TADF1 obtained by the method of Example 1.

›Example 1a · 2 of 2

It should be noted that the intermediate B used in Example 1a was prepared by the same method as the synthesis method of the intermediate B in Example 1,

›Example 2

(2) Synthesis Example 2: Synthesis of Compound TADF2

(2-1) Synthesis of TADF2

Under nitrogen atmosphere, to a 50-mL Schlenk tube, 7,7-dimethyl-5H-indeno[2,1-b]carbazole (0.63 g, 2.2 mmol), potassium carbonate (0.62 g, 4.4 mmol), the intermediate C (0.5 g, 1.0 mmol), and DMF (10 mL) were added and stirred at 60 degrees C. for six hours. After the reaction, the mixture was cooled to the room temperature (25 degrees C.). Water (30 mL) was added to the mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (0.82 g). The solid was identified as TADF2 by analysis according to ASAP-MS (a yield rate: 79%).

›Example 3

(3) Synthesis Example 3: Synthesis of Compound TADF3

(3-1) Synthesis of Intermediate D

Under nitrogen atmosphere, to a 50-mL Schlenk tube, 11H-benzo[a]carbazole (0.07 g, 0.32 mmol), potassium carbonate (0.09 g, 0.65 mmol), the intermediate D (0.1 g, 0.15 mmol), and DMF (3 mL) were added and stirred at 60 degrees C. for six hours. After the reaction, the mixture was cooled to the room temperature (25 degrees C.). Water (20 mL) was added to the mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (0.032 g). The solid was identified as TADF3 by analysis according to ASAP-MS (a yield rate: 20%).

›Example 4

(4) Synthesis Example 4: Synthesis of Compound TADF4

(4-1) Synthesis of Intermediate E

Under nitrogen atmosphere, into a 500-mL three-necked flask, carbazole (17 g, 100 mmol), N,N-diisopropylethylamine (iPr 2 NEt) (21 g, 150 mmol), tetrafluoroisophthalonitrile (8 g, 40 mmol), and N,N-dimethyl formamide (DMF) (200 mL) were put and heated at 60 degrees C. with stirring. After hour hours, water (1000 mL) was added to the reactant mixture. The deposited solid was purified by silica-gel column chromatography to obtain a yellow solid (7.5 g). The solid was identified as an intermediate E by analysis according to ASAP-MS and 1 H-NMR (a yield rate: 38%).

(4-2) Synthesis of TADF4

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate B (1.9 g, 7.5 mmol), sodium hydride (containing oil at 40 mass %)(0.3 g, 7.5 mmol), and tetrahydrofuran (THF) (38 mL) were put, and stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate E (1.5 g, 3 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added to water (200 mL). The deposited solid was purified by silica-gel column chromatography to obtain an orange solid (2.47 g). The solid was identified as TADF4 by analysis according to ASAP-MS (a yield rate: 85%).

›Example 5

(5) Synthesis Example 5: Synthesis of Compound TADF5

(5-1) Synthesis of Intermediate F

Under nitrogen atmosphere, into a 300-mL three-necked flask, 11H-benzo[a]carbazole (10 g, 50 mmol), sodium hydride (containing oil at 40 mass %)(2 g, 50 mmol), and tetrahydrofuran (THF) (200 mL) were put, and stirred at the room temperature (25 degrees C.) for 30 minutes. Next, tetrafluoroisophthalonitrile (2.5 g, 12.5 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added to water (200 mL). The deposited solid was purified by silica-gel column chromatography to obtain an orange solid (7.2 g). The solid was identified as an intermediate F by analysis according to ASAP-MS and 1 H-NMR (a yield rate: 73%).

(5-2) Synthesis of TADF5

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate B (0.77 g, 3.0 mmol), sodium hydride (containing oil at 40 mass %) (0.12 g, 3.0 mmol), and tetrahydrofuran (THF) (20 mL) were put, and stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate F (2.0 g, 2.5 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added to water (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.57 g). The solid was identified as TADF5 by analysis according to ASAP-MS (a yield rate: 61%).

›Example 6

(6) Synthesis Example 6: Synthesis of Compound TADF6

(6-1) Synthesis of Intermediate G

Under nitrogen atmosphere, into a 500-mL three-necked flask, the intermediate B (13 g, 50 mmol), N,N-diisopropylethylamine (iPr 2 NEt) (10 g, 75 mmol), tetrafluorophthalonitrile (20 g, 100 mmol), and N,N-dimethyl formamide (DMF) (250 mL) were put and stirred at the room temperature (25 degrees C.). After 12 hours, water (200 mL) was added to the mixture. The deposited solid was purified by silica-gel column chromatography to obtain an orange solid (9.8 g). The solid was identified as an intermediate F by analysis according to ASAP-MS (a yield rate: 45%).

(6-2) Synthesis of TADF6

Under nitrogen atmosphere, to a 50-mL Schlenk tube, the intermediate C (1.0 g, 2.0 mmol), potassium carbonate (1.4 g, 10.0 mmol), 5H-Benzo[4,5]thieno[3,2-c]carbazole (1.4 g, 5.0 mmol), and DMF (20 mL) were added and stirred at 60 degrees C. for six hours. After the reaction, the mixture was cooled to the room temperature (25 degrees C.). Water (30 mL) was added to the mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.60 g). The solid was identified as TADF8 by analysis according to ASAP-MS (a yield rate: 80%).

›Example 9

(9) Synthesis Example 9: Synthesis of Compound TADF9

(9-1) Synthesis of Intermediate K

Under nitrogen atmosphere, 2M sodium carbonate aqueous solution (100 mL, 200 mmol), 1,2-dimethoxyethane (DME) (200 mL), toluene (200 mL), and tetrakis(triphenylphosphine)palladium(0) (Pd[PPh 3]4 ) (5.7 g, 5.0 mmol) were added to 2-bromonitrobenzene (20.0 g, 99.0 mmol) and 1-dibenzofuran boronic acid (25.2 g, 118.8 mmol) and the obtained mixture was heated to reflux with stirring for 12 hours.

After the reaction, the mixture was cooled to the room temperature (25 degrees C.). A sample was transferred to a separating funnel, added with water (500 mL), and extracted with dichloromethane. The extracted sample was dried over MgSO 4 , filtered and condensed. The sample was purified by silica-gel column chromatography to obtain a white solid (20.0 g). The solid was identified as an intermediate L by analysis according to FD-MS (a yield rate: 70%).

(10-2) Synthesis of Intermediate M

Under argon atmosphere, orthodichlorobenzen (ODCB) (150 mL) was added to the intermediate L (20.0 g, 69.0 mmol) and triphenylphosphine (45.2 g, 172.5 mmol), and the obtained mixture was heated to reflux with stirring for 24 hours. After the reaction, the mixture was cooled to the room temperature (25 degrees C.). A sample was transferred to a separating funnel, added with water (400 mL), and extracted with dichloromethane. The extracted sample was dried over MgSO 4 , filtered and condensed. The sample was purified by silica-gel column chromatography to obtain a white solid (9.0 g). The solid was identified as an intermediate M by analysis according to FD-MS (a yield rate: 51%).

(10-3) Synthesis of TADF10

Under nitrogen atmosphere, into a 500-mL three-necked flask, the intermediate B (6.5 g, 25 mmol), triethylamine (Et 3 N) (5.1 g, 50 mmol), tetrafluoroterephthalonitrile (20 g, 100 mmol), and N,N-dimethylacetamide (DMAc) (250 mL) were put. After heated with stirring for ten hours at 60 degrees C., the mixture was returned to the room temperature (25 degrees C.) and added with water (500 mL). The deposited solid was purified by silica-gel column chromatography to obtain a yellow solid (0.66 g). The solid was identified as an intermediate 0 by analysis according to ASAP-MS (a yield rate: 6%).

(12-2) Synthesis of TADF12

Under nitrogen atmosphere, into a 100-mL three-necked flask, carbazole (0.77 g, 4.62 mmol), sodium hydride (0.18 g (60 mass %, dispersed in liquid paraffin), 4.62 mmol), and tetrahydrofuran (THF) (20 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate 0 (0.5 g, 1.1 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added with water (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a red solid (0.87 g). The solid was identified as TADF12 by analysis according to ASAP-MS (a yield rate: 90%).

›Example 13

(13) Synthesis Example 13: Synthesis of Compound TADF13

(13-1) Synthesis of Intermediate V1

Under nitrogen atmosphere, 2M sodium carbonate aqueous solution (220 mL, 435 mmol), 1,2-dimethoxyethane (DME) (440 mL), and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride-dichloromethane adduct (Pd(dppf)Cl 2 .CH 2 Cl 2 ) (2.4 g, 2.9 mmol) were added to 3-chloro-4-nitrotoluene (25.0 g, 145 mmol) and 4-dibenzofuran boronic acid (30.7 g, 145 mmol). The obtained mixture was heated to reflux with stirring for four hours.

After the reaction, the mixture was cooled to the room temperature (25 degrees 0). A sample was transferred to a separating funnel, added with water (500 mL), and extracted with ethyl acetate. The extracted sample was dried over MgSO 4 , filtered and condensed. The sample was purified by silica-gel column chromatography to obtain a yellow solid (35 g). The solid was identified as an intermediate V1 by analysis according to GC-MS (GasChromatograph Mass Spectrometry) (a yield rate: 80%).

(13-2) Synthesis of Intermediate V2

25 mmol), the intermediate V2 (10.2 g, 37.5 mmol), triethylamine (Et 3 N) (5.3 mL, 37.5 mmol), and DMSO (150 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.). After ten hours, water (200 mL) was added to the mixture. The deposited solid was collected by filtration using a Kiriyama funnel. The obtained solid was purified by silica-gel column chromatography to obtain a yellow solid (5.0 g). The solid was identified as an intermediate R by analysis according to ASAP-MS (a yield rate: 38%).

(13-4) Synthesis of TADF13

Under nitrogen atmosphere, into a 100-mL three-necked flask, carbazole (3 g, 18 mmol), sodium hydride (0.72 g (60 mass %, dispersed in liquid paraffin), 18 mmol), and tetrahydrofuran (THF) (100 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate R (1.5 g, 8.2 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added with water (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain an orange solid (4.5 g). The solid was identified as TADF13 by analysis according to ASAP-MS (a yield rate: 78%).

›Example 14

(14) Synthesis Example 14: Synthesis of Compound TADF14

(14-1) Synthesis of Intermediate S

Under nitrogen atmosphere, into a 500-mL three-necked eggplant flask, tetrafluoroisophthalonitrile (5.0 g, 25 mmol), 8H-benzo[4,5]thieno[2,3-c]carbazole (10.2 g, 37.5 mmol), triethylamine (Et 3 N) (5.3 mL, 37.5 mmol), and DMSO (150 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.). After eight hours, water (200 mL) was added to the mixture. The deposited solid was collected by filtration using a Kiriyama funnel. The obtained solid was purified by silica-gel column chromatography to obtain a yellow solid (8.5 g). The solid was identified as an intermediate S by analysis according to ASAP-MS (a yield rate: 64%).

(14-2) Synthesis of TADF14

Under nitrogen atmosphere, into a 100-mL three-necked flask, carbazole (3 g, 18 mmol), sodium hydride (0.72 g (60 mass %, dispersed in liquid paraffin), 18 mmol), and tetrahydrofuran (THF) (100 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate S (1.5 g, 8.2 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added with water (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain an orange solid (2.8 g). The solid was identified as TADF14 by analysis according to ASAP-MS (a yield rate: 34%).

›Example 15

(15) Synthesis Example 15: Synthesis of Compound TADF15

(15-1) Synthesis of Intermediate T

Under nitrogen atmosphere, into a 500-mL three-necked flask, the intermediate B (6.5 g, 25 mmol), triethylamine (5.1 g, 50 mmol), tetrafluoroterephthalonitrile (20 g, 100 mmol), and N,N-dimethylacetamide (DMAc) (250 mL) were put. After heated with stirring for ten hours at 40 degrees C., the mixture was returned to the room temperature (25 degrees C.) and added with water (500 mL). The deposited solid was purified by silica-gel column chromatography to obtain a yellow solid (0.98 g). The solid was identified as an intermediate T by analysis according to ASAP-MS (a yield rate: 9%).

(15-2) Synthesis of TADF15

Under nitrogen atmosphere, into a 100-mL three-necked flask, carbazole (0.61 g, 3.63 mmol), sodium hydride (0.15 g (60 mass %, dispersed in liquid paraffin), 3.63 mmol), and tetrahydrofuran (THF) (20 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate 0 (0.8 g, 1.1 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added with water (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.3 g). The solid was identified as TADF15 by analysis according to ASAP-MS (a yield rate: 81%).

›Example 16

(16) Synthesis Example 16: Synthesis of Compound TADF16

(16-1) Synthesis of Intermediate U

Under nitrogen atmosphere, into a 500-mL three-necked flask, the intermediate B (6.8 g, 25 mmol), triethylamine (Et 3 N)(5.1 g, 50 mmol), tetrafluoroterephthalonitrile (25 g, 125 mmol), and N,N-dimethylacetamide (DMAc) (250 mL) were put. After heated with stirring for ten hours at 40 degrees C., the mixture was returned to the room temperature (25 degrees C.) and added with water (500 mL). The deposited solid was purified by silica-gel column chromatography to obtain a yellow solid (1.5 g). The solid was identified as an intermediate U by analysis according to ASAP-MS (a yield rate: 13%).

(16-2) Synthesis of TADF16

Under nitrogen atmosphere, into a 100-mL three-necked flask, carbazole (1.20 g, 7.26 mmol), sodium hydride (0.17 g (60 mass %, dispersed in liquid paraffin), 7.26 mmol), and tetrahydrofuran (THF) (20 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate U (1.0 g, 2.2 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added with water (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.7 g). The solid was identified as TADF16 by analysis according to ASAP-MS (a yield rate: 85%).

›Example 17

(17) Synthesis Example 17: Synthesis of Compound TADF17

(17-1) Synthesis of TADF17

Under nitrogen atmosphere, into a 100-mL three-necked flask, 12H-[1]Benzothieno[2,3-a]carbazole (1.98 g, 7.27 mmol), sodium hydride (0.29 g (60 mass %, dispersed in liquid paraffin), 7.27 mmol), and DMF (30 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate C (1.5 g, 3.0 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added with a saturated aqueous solution of ammonium chloride (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a red solid (2.0 g). The solid was identified as TADF18 by analysis according to ASAP-MS (a yield rate: 66%).

›Example 19

(19) Synthesis Example 19: Synthesis of Compound TADF19

(19-1) Synthesis of TADF19

Under nitrogen atmosphere, into a 100-mL three-necked flask, 12H-Benzofuro[3,2-a]carbazole (1.20 g, 7.26 mmol), sodium hydride (0.29 g (60 mass %, dispersed in liquid paraffin), 7.26 mmol), and DMF (40 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees 0) for 30 minutes. Next, the intermediate C (1.0 g, 2.2 mmol) was put into the reactant mixture, After two hours, the reactant mixture was added with a saturated aqueous solution of ammonium chloride (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.1 g). The solid was identified as TADF19 by analysis according to ASAP-MS (a yield rate: 52%).

Compounds in Examples 20 to 27 were synthesized using at least one of intermediates P, Q, A 1 to A 4 and C2 to J2 below. The intermediates P, Q, A 1 to A 4 and C2 to J2 were synthesized by the following method.

Synthesis of Intermediate P and Intermediate Q

Under nitrogen atmosphere, 2M sodium carbonate aqueous solution (220 mL, 435 mmol), 1,2-dimethoxyethane (DME) (440 mL), and dichlorobis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium (II) ((AMPHOS) 2 PdCl 2 ) (2.1 g, 2.9 mmol) were added to 3-chloro-4-nitrotoluene (25.0 g, 146 mmol) and 4-dibenzothiophene boronic acid (34 g, 146 mmol). The obtained mixture was heated to reflux with stirring for four hours.

After the reaction, the mixture was cooled to the room temperature (25 degrees C.). A sample was transferred to a separating funnel, added with water (500 mL), and extracted with ethyl acetate. The extracted sample was dried over MgSO 4 , filtered and condensed. The sample was purified by silica-gel column chromatography to obtain a yellow solid (40 g). The solid was identified as an intermediate P by analysis according to GC-MS (a yield rate: 86%).

Under argon atmosphere, orthodichlorobenzene (ODCB) (240 mL) was added to the intermediate P (15.0 g, 47 mmol) and triphenylphosphine (31 g, 117 mmol), and the obtained mixture was heated to reflux with stirring for 20 hours. After the reaction, the mixture was cooled to the room temperature (25 degrees C.). The reactant solution was condensed using an evaporator. The obtained solid was purified by silica-gel column chromatography to obtain a white solid (8.4 g). The solid was identified as an intermediate Q by analysis according to GC-MS (a yield rate: 62%).

Synthesis of Intermediate A 1 and Intermediate A 2

Under nitrogen atmosphere, to a three-necked flask, 4-bromodibenzothiophene (26.0 g, 100 mmol), 2-chloro-4-methylaniline (17 g, 120 mmol), tris(dibenzylidene acetone)dipalladium(0) (Pd 2 dba 3 ) (0.9 g, 1 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu) 3 HBF 4 ) (2.3 g, 8 mmol), sodium tert-butoxide (NaOtBu) (11.5 g, 120 mmol) and toluene (350 mL) were added. The obtained mixture was heated with stirring at 60 degrees C. for seven hours, and then cooled to the room temperature (25 degrees C.). The reactant solution was purified by silica-gel column chromatography to obtain a white solid (26 g). The solid was identified as an intermediate C 2 by analysis according to GC-MS (a yield rate: 80%).

Under nitrogen atmosphere, to a 1-L three-necked flask, the intermediate C (26.0 g, 80 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazorium chloride(IPrHCl)(1.4 g, 3.2 mmol), palladium acetate(II)(Pd(OAc) 2 ) (0.36 g, 1.6 mmol), potassium carbonate (22.0 g, 160 mmol) and N,N-dimethylacetamide (DMAc) (400 mL) were added. The obtained mixture was stirred at 130 degrees C. for seven hours and then cooled to the room temperature (25 degrees C.). The reactant solution was purified by silica-gel column chromatography to obtain a white solid (21 g). The solid was identified as an intermediate D 2 by analysis according to GC-MS (a yield rate: 91%).

Synthesis of Intermediate E2 and Intermediate F2

Under nitrogen atmosphere, to a 1-L three-necked flask, 4-bromodibenzothiophene (26.0 g, 100 mmol), 2-chloro-4,6-dimethylaniline (18.7 g, 120 mmol), tris(dibenzylidene acetone)dipalladium(0) (0.9 g, 1 mmol), tri-tert-butylphosphonium tetrafluoroborate (2.3 g, 8 mmol), sodium tert-butoxide (11.5 g, 120 mmol) and toluene (350 mL) were added. The obtained mixture was heated with stirring at 60 degrees C. for seven hours, and then cooled to the room temperature (25 degrees C.). The reactant solution was purified by silica-gel column chromatography to obtain a white solid (23.7 g). The solid was identified as an intermediate G2 by analysis according to GC-MS (a yield rate: 70%).

Under nitrogen atmosphere, to a 1-L three-necked flask, the intermediate C (23.0 g, 68 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazorium chloride(IPrHCl)(1.2 g, 2.71 mmol), palladium acetate(II) (0.31 g, 1.36 mmol), potassium carbonate (18.8 g, 136 mmol) and N,N-dimethylacetamide (DMAc) (400 mL) were added. The obtained mixture was stirred at 130 degrees C. for seven hours and then cooled to the room temperature (25 degrees C.). The reactant solution was purified by silica-gel column chromatography to obtain a white solid (19.5 g). The solid was identified as an intermediate H 2 by analysis according to GC-MS (a yield rate: 95%).

Synthesis of Intermediate 12 and Intermediate J2

Under nitrogen atmosphere, to a 1-L three-necked flask, 4-bromodibenzofuran (26.0 g, 100 mmol), 2-chloro-4,6-dimethylaniline (17 g, 120 mmol), tris(dibenzylidene acetone)dipalladium(0) (0.9 g, 1 mmol), tri-tert-butylphosphonium tetrafluoroborate (2.3 g, 8 mmol), sodium tert-butoxide (11.5 g, 120 mmol) and toluene (350 mL) were added. The obtained mixture was heated with stirring at 60 degrees C. for seven hours, and then cooled to the room temperature (25 degrees C.). The reactant solution was purified by silica-gel column chromatography to obtain a white solid (28 g). The solid was identified as an intermediate 12 by analysis according to GC-MS (a yield rate: 88%).

Under nitrogen atmosphere, to a 1-L three-necked flask, the intermediate C (28 g, 88 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazorium chloride (IPrHCl) (1.5 g, 3.5 mmol), palladium acetate(II) (0.4 g, 1.76 mmol), potassium carbonate (24.3 g, 176 mmol) and N,N-dimethylacetamide (DMAc) (450 mL) were added. The obtained mixture was stirred at 130 degrees C. for seven hours and then cooled to the room temperature (25 degrees C.). The reactant solution was purified by silica-gel column chromatography to obtain a white solid (21 g). The solid was identified as an intermediate J2 by analysis according to GC-MS (a yield rate: 85%).

›Example 20

(20) Synthesis Example 20: Synthesis of Compound TADF20

(20-1) Synthesis of TADF20

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate A 3 (2 g, 3.0 mmol), the intermediate Q (1.0 g, 3.6 mmol), potassium carbonate (0.6 g, 4.5 mmol) and DMF (30 mL) were put. The obtained mixture was stirred at 70 degrees C. for eight hours. A saturated aqueous solution of ammonium chloride (50 mL) was added to the reactant mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.6 g). The solid was identified as TADF20 by analysis according to ASAP-MS (a yield rate: 59%).

›Example 21

(21) Synthesis Example 21: Synthesis of Compound TADF21

(21-1) Synthesis of TADF21

Under nitrogen atmosphere, to a 100-mL three-necked flask, the intermediate A 3 (2 g, 3.0 mmol), 12H-[1]Benzothieno[2,3-a]carbazole (0.98 g, 3.6 mmol), potassium carbonate (0.6 g, 4.5 mmol) and DMF (30 mL) were put. The obtained mixture was stirred at 70 degrees C. for eight hours. A saturated aqueous solution of ammonium chloride (50 mL) was added to the reactant mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.5 g). The solid was identified as TADF21 by analysis according to ASAP-MS (a yield rate: 56%).

›Example 22

(22) Synthesis Example 22: Synthesis of Compound TADF22

(22-1) Synthesis of TADF22

Under nitrogen atmosphere, to a 100-mL three-necked flask, the intermediate A 3 (2 g, 3.0 mmol), the intermediate D 2 (1.0 g, 3.6 mmol), potassium carbonate (0.6 g, 4.5 mmol) and DMF (30 mL) were put. The obtained mixture was stirred at 70 degrees C. for eight hours. A saturated aqueous solution of ammonium chloride (50 mL) was added to the reactant mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.8 g). The solid was identified as TADF22 by analysis according to ASAP-MS (a yield rate: 66%).

›Example 23

(23) Synthesis Example 23: Synthesis of Compound TADF23

(23-1) Synthesis of TADF23

Under nitrogen atmosphere, to a 100-m1 three-necked flask, the intermediate C (1.0 g, 2.0 mmol), potassium carbonate (0.28 g, 5.0 mmol) and the intermediate Q (1.4 g, 5.0 mmol), and DMF (30 m1) were added. The obtained mixture was stirred at 70 degrees C. for six hours.

After the reaction, the mixture was cooled to the room temperature (25 degrees C.) A saturated aqueous solution of ammonium chloride (50 mL) was added to the reactant mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.8 g). The solid was identified as TADF23 by analysis according to ASAP-MS (a yield rate: 88%).

›Example 24

(24) Synthesis Example 24: Synthesis of Compound TADF24

(24-1) Synthesis of TADF24

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate F2 (2.00 g, 7.38 mmol), sodium hydride (0.30 g (60 mass %, dispersed in liquid paraffin), 7.38 mmol), and DMF (30 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate C (1.68 g, 3.4 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added with a saturated aqueous solution of ammonium chloride (50 mL). The deposited solid was purified by silica-gel column chromatography to obtain an orange solid (2.8 g). The solid was identified as TADF24 by analysis according to ASAP-MS (a yield rate: 83%).

›Example 25

(25) Synthesis Example 25: Synthesis of Compound TADF25

(25-1) Synthesis of TADF25

Under nitrogen atmosphere, to a 100-mL three-necked flask, the intermediate A 3 (2 g, 3.0 mmol), the intermediate J2 (1.0 g, 3.6 mmol), potassium carbonate (0.6 g, 4.5 mmol) and DMF (30 mL) were put. The obtained mixture was stirred at 70 degrees C. for eight hours. A saturated aqueous solution of ammonium chloride (50 mL) was added to the reactant mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.2 g). The solid was identified as TADF26 by analysis according to ASAP-MS (a yield rate: 44%).

›Example 27

(27) Synthesis Example 27: Synthesis of Compound TADF27

(27-1) Synthesis of TADF27

Under nitrogen atmosphere, to a 100-mL three-necked flask, the intermediate A 4 (1.9 g, 3.0 mmol), the intermediate H 2 (1.1 g, 3.6 mmol), potassium carbonate (0.6 g, 4.5 mmol) and DMF (30 mL) were put. The obtained mixture was stirred at 70 degrees C. for eight hours. A saturated aqueous solution of ammonium chloride (50 mL) was added to the reactant mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.4 g). The solid was identified as TADF27 by analysis according to ASAP-MS (a yield rate: 51%).

›Example 28

(28) Synthesis Example 28: Synthesis of Compound TADF28

(28-1) Synthesis of Intermediate M2 and Intermediate N2

Under nitrogen atmosphere, to a 1-L three-necked flask, 2-bromodibenzofuran (12.4 g, 50 mmol), 2-chlorolaniline (7.5 g, 60 mmol), tris(dibenzylidene acetone)dipalladium(0) (0.45 g, 0.5 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.2 g, 4 mmol), sodium tert-butoxide (5.8 g, 60 mmol) and toluene (200 mL) were added. The obtained mixture was heated with stirring at 80 degrees C. for six hours, and then cooled to the room temperature (25 degrees C.). The reactant solution was purified by silica-gel column chromatography to obtain a white solid (13.5 g). The solid was identified as an intermediate M2 by analysis according to GC-MS (a yield rate: 92%).

Under nitrogen atmosphere, to a 1-L three-necked flask, the intermediate M2 (13.5 g, 46 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazorium chloride (IPrHCl) (0.81 g, 3.6 mmol), palladium acetate(II) (0.21 g, 0.92 mmol), potassium carbonate (12.7 g, 92 mmol) and N,N-dimethylacetamide (DMAc) (400 mL) were added. The obtained mixture was stirred at 130 degrees C. for four hours and then cooled to the room temperature (25 degrees C.). The reactant solution was purified by silica-gel column chromatography to obtain a white solid (6.0 g). The solid was identified as an intermediate N2 by analysis according to GC-MS (a yield rate: 51%).

(28-2) Synthesis of TADF28

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate N2 (2.16 g, 8.4 mmol), sodium hydride (0.34 g (60 mass %, dispersed in liquid paraffin), 3.4 mmol), and DMF (50 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate C (2.00 g, 4.0 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added with a saturated aqueous solution of ammonium chloride (30 mL). The deposited solid was purified by silica-gel column chromatography to obtain an orange solid (3.00 g). The solid was identified as TADF28 by analysis according to ASAP-MS (a yield rate: 78%).

›Example 29

(29) Synthesis Example 29: Synthesis of Compound TADF29

(29-1) Synthesis of Intermediate 02

Under nitrogen atmosphere, to a 500-mL three-necked flask, carbazole (17 g, 100 mmol), tetramethylpiperidine (TMP) (22 g, 150 mmol), tetrafluoroisophthalonitrile (6.6 g, 33 mmol), and acetonitrilel (CH 3 CN) (200 mL) were put. The obtained mixture was heated with stirring at 80 degrees C. for four hours. A solvent was distilled away from the reactant solution using an evaporator. The obtained solid was purified by silica-gel column chromatography to obtain a yellow solid (13 g). The solid was identified as an intermediate O2 by analysis according to ASAP-MS (a yield rate: 65%).

(29-2) Synthesis of TADF29

Under nitrogen atmosphere, into a 100-mL three-necked flask, 12H-[1]Benzothieno[2,3-a]carbazole (2.02 g, 7.27 mmol), sodium hydride (0.29 g (60 mass %; dispersed in liquid paraffin), 7.27 mmol), and DMF (30 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate O2 (3.9 g, 5.59 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added with a saturated aqueous solution of ammonium chloride (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a red solid (2.9 g). The solid was identified as TADF29 by analysis according to ASAP-MS (a yield rate: 58%).

›Example 30

(30) Synthesis Example 30: Synthesis of Compound TADF30

(30-1) Synthesis of TADF30

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate D 2 (2.30 g, 8.00 mmol), sodium hydride (0.32 g (60 mass %, dispersed in liquid paraffin), 8.00 mmol), and DMF (40 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate O2 (3.4 g, 5.33 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added with a saturated aqueous solution of ammonium chloride (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a yellow solid (3.0 g). The solid was identified as TADF30 by analysis according to ASAP-MS (a yield rate: 61%).

›Example 31

(31) Synthesis Example 31: Synthesis of Compound TADF31

(31-1) Synthesis of TADF31

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate J (2.00 g, 7.19 mmol), sodium hydride (0.29 g (60 mass %, dispersed in liquid paraffin), 7.19 mmol), and DMF (30 were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate O2 (3.9 g, 5.59 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added to a saturated aqueous solution of ammonium chloride (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a yellow solid (3.3 g). The solid was identified as TADF31 by analysis according to ASAP-MS (a yield rate: 66%).

›Example 32

(32) Synthesis Example 32: Synthesis of Compound TADF32

(32-1) Synthesis of TADF32

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate D 2 (1.4 g, 5.0 mmol), sodium hydride (containing oil at 40 mass %) (0.2 g, 5.0 mmol), and DMF (40 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate E (1.0 g, 2 mmol) was put into the reactant mixture. The obtained mixture was stirred for two hours. Subsequently, the obtained reactant mixture was added to water (50 mL). The deposited solid was purified by silica-gel column chromatography to obtain an orange solid (1.85 g). The solid was identified as TADF32 by analysis according to ASAP-MS (a yield rate: 90%).

›Example 33

(33) Synthesis Example 33: Synthesis of Compound TADF33

(33-1) Synthesis of TADF33

Under nitrogen atmosphere, into a 100-mL three-necked flask, 12H-Benzofuro[3,2-a]carbazole (1.3 g, 5.0 mmol), sodium hydride (containing oil at 40 mass %) (0.2 g, 5.0 mmol), and DMF (40 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate E (1.0 g, 2 mmol) was put into the reactant mixture. The obtained mixture was stirred for two hours. Subsequently, the obtained reactant mixture was added to water (50 mL). The deposited solid was purified by silica-gel column chromatography to obtain an orange solid (1.70 g). The solid was identified as TADF33 by analysis according to ASAP-MS (a yield rate: 88%).

›Example 34

(34) Synthesis Example 34: Synthesis of Compound TADF34

(34-1) Synthesis of TADF34

Under nitrogen atmosphere, into a 100-mL three-necked flask, 12H-Benzofuro[2,3-a]carbazole (1.87 g, 7.27 mmol), sodium hydride (0.29 g (60 mass %, dispersed in liquid paraffin), 7.27 mmol), and DMF (30 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate O2 (3.9 g, 5.59 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added to a saturated aqueous solution of ammonium chloride (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a yellow solid (3.5 g). The solid was identified as TADF34 by analysis according to ASAP-MS (a yield rate: 71%).

›Example 35

(35) Synthesis Example 35: Synthesis of Compound TADF35

(35-1) Synthesis of TADF35

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate V2 (2.00 g, 7.38 mmol), sodium hydride (0.30 g (60 mass %, dispersed in liquid paraffin), 7.38 mmol), and DMF (40 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate O2 (4.0 g, 5.68 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added to a saturated aqueous solution of ammonium chloride (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a yellow solid (4.0 g). The solid was identified as TADF35 by analysis according to ASAP-MS (a yield rate: 79%).

›Example 36

(36) Synthesis Example 36: Synthesis of Compound TADF36

(36-1) Synthesis of TADF36

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate Q (2.00 g, 7.00 mmol), sodium hydride (0.28 g (60 mass %, dispersed in liquid paraffin), 7.00 mmol), and DMF (40 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate O2 (3.6 g, 5.38 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added to a saturated aqueous solution of ammonium chloride (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a yellow solid (2.6 g). The solid was identified as TADF36 by analysis according to ASAP-MS (a yield rate: 61%).

›Example 37

(37) Synthesis Example 37: Synthesis of Compound TADF37

(37-1) Synthesis of Intermediate P2

Under nitrogen atmosphere, into a 1000-mL three-necked flask, the intermediate A2 (1.16 g, 5.35 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (whose deuterium ratio of 98% was used)(3 g, 17.1 mmol), potassium carbonate (3.5 g, 25.7 mmol) and DMF (30 mL) were put. The obtained mixture was stirred at 0 degrees C. for nine hours. The reactant mixture was added to a saturated aqueous solution of ammonium chloride (30 mL). The deposited solid was purified by silica-gel column chromatography to obtain a yellow solid (3.0 g). The solid was identified as an intermediate P2 by analysis according to ASAP-MS (a yield rate: 82%).

(37-2) Synthesis of TADF37

Under nitrogen atmosphere, 1 into a 100-mL three-necked flask, the intermediate P2 (2.6 g, 3.8 mmol), the intermediate D 2 (1.6 g, 5.7 mmol), potassium carbonate (1.2 g, 8.9 mmol) and DMF (30 mL) were put. The obtained mixture was stirred at 115 degrees C. for six hours. A saturated aqueous solution of ammonium chloride (50 mL) was added to the reactant mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (2.5 g). The solid was identified as TADF37 by analysis according to ASAP-MS (a yield rate: 70%).

›Example 38

(38) Synthesis Example 38: Synthesis of Compound TADF38

(38-1) Synthesis of TADF38

Under nitrogen atmosphere, into a 100-mL three-necked flask, the intermediate P2 (3.0 g, 4.4 mmol), the intermediate Q (1.6 g, 5.7 mmol), potassium carbonate (1.2 g, 8.6 mmol) and DMF (30 mL) were put. The obtained mixture was stirred at 115 degrees C. for six hours. A saturated aqueous solution of ammonium chloride (50 mL) was added to the reactant mixture. The deposited solid was purified by silica-gel column chromatography to obtain a red solid (3.3 g). The solid was identified as TADF38 by analysis according to ASAP-MS (a yield rate: 80%).

›Example 39 · 1 of 2

(39) Synthesis Example 39: Synthesis of Compound TADF39

(39-1) Synthesis of Intermediate K2 and Intermediate L 2

Under nitrogen atmosphere, into a 200-mL three-necked flask, the intermediate L 2 (1.82 g, 6.67 mmol), sodium hydride (0.26 g (60 mass %, dispersed in liquid paraffin), 6.67 mmol), and DMF (60 mL) were put, and the obtained mixture was stirred at the room temperature (25 degrees C.) for 30 minutes. Next, the intermediate C (1.5 g, 3.0 mmol) was put into the reactant mixture. After two hours, the reactant mixture was added to a saturated aqueous solution of ammonium chloride (100 mL). The deposited solid was purified by silica-gel column chromatography to obtain a red solid (1.8 g). The solid was identified as TADF39 by analysis according to ASAP-MS (a yield rate: 61%).

Comparatives 1 to 3

Comparative compounds 1 to 3 were synthesized by a method in conformity with the method of synthesizing the compound TADF1.

Evaluation of Compounds

Methods of measuring properties of the compounds are shown below.

Weight Reduction Temperature

A 1%-weight loss temperature and a 5%-weight loss temperature were measured under the following conditions using a differential thermogravimetric simultaneous measurement device.

Results are shown in Table 59.

Thermogravimetric differential calorimetry (TG-DTA), which is a method of continuously measuring a change in mass of a sample when the sample is heated, is used for detecting a physical change accompanied by the change in mass such as sublimation and evaporation.

Accordingly, in this evaluation, the “high” weight loss temperature obtained by TG-DTA is regarded as a “high” sublimation temperature under high vacuum while the “low” weight loss temperature obtained by TG-DTA is regarded as a “low” sublimation temperature under high vacuum. Herein, “under high vacuum” refers to a range from 1.0×10 −6 Pa to 1.0×10 −3 Pa.

Measurement Conditions

Device: differential thermogravimetric simultaneous measurement device (STA7200RV manufactured by Hitachi High Technologies)

Container: aluminum pan

Mass of Sample: 3.0 mg

Measurement atmosphere: nitrogen gas atmosphere

Temperature Increase Rate: 10 degrees C. per minute

Measurement Range: from 35 to 600 degrees C.

Sublimation Temperature

A sublimation temperature of each of the compounds was measured under the following conditions using a vacuum evaporation apparatus.

Results are shown in Table 59.

Measurement Conditions Pressure: 10 −5 Pa

Temperature: from 300 to 400 degrees C.

Heating Time: from 5 to 10 minutes

Delayed Fluorescence

Delayed Fluorescence of Compound TADF1

Delayed fluorescence was checked by measuring a transient PL using an apparatus shown in FIG. 2 . A dilute solution was prepared by dissolving the compound TADF1 in toluene, the dilute solution (sample solution) having an absorbance of 0.05 or less at an excitation wavelength in order to remove contribution of self-absorption. Moreover, in order to prevent quenching due to oxygen, the sample solution was frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.

Fluorescence spectrum of the sample solution was measured with a spectrophotofluorometer FP-8600 (manufactured by JASCO Corporation). Moreover, fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was measured under the same conditions. Using fluorescence area intensities of both the spectra, a total fluorescence quantum yield was calculated according to the equation (1) in Morris et al. J. Phys. Chem. 80(1976) 969 .

Prompt emission was observed immediately when the excited state was achieved by exciting the compound TADF1 with a pulse beam (i.e., a beam emitted from a pulse laser) having a wavelength to be absorbed by the compound TADF1, and Delay emission was observed not immediately when the excited state was achieved but after the excited state was achieved. Delayed fluorescence in Examples means that an amount of Delay emission is 5% or more relative to an amount of Prompt emission. Specifically, the delayed fluorescence means that a value of X D /X P is 0.05 or more, provided that the amount of Prompt emission is denoted by X P and the amount of Delay emission is denoted by X D .

The amount of Prompt emission, the amount of Delay emission, and a ratio thereof can be obtained according to the method as described in “Nature 492, 234-238, 2012” (Reference Literature 1). A device used for calculating the amount of Prompt emission and the amount of Delay emission is not limited to the device described in Reference Literature 1 or FIG. 2 .

It was confirmed that the amount of Delay emission was 5% or more relative to the amount of Prompt emission in the compound TADF1. Specifically, it was confirmed that the value of X D /X P was 0.05 or more in the compound TADF1.

Delayed Fluorescence of Compounds TADF 2 to 39 and Comparative Compounds 1 to 3

Compounds TADF 2 to 39 and comparative compounds 1 to 3 were checked in terms of delayed fluorescence in the same manner as above except that the compound TADF1 was replaced by compounds TADF 2 to 39 and comparative compounds 1 to 3.

It was confirmed that the value of X D /X P was 0.05 or more in the compound compounds TADF 2 to 39 and comparative compounds 1 to 3.

Singlet Energy S 1

The compounds TADF1 to 39, the comparative compounds 1 to 3, and compounds RD-1 to RD-4 and CBP were measured in terms of singlet energy S 1 by the above solution method. Results are shown in Table 59.

Measurement results of the compounds RD-1 to RD-4 and CBP are as follows.

A singlet energy S 1 of the compound RD-1 was 2.02 eV.

A singlet energy S 1 of the compound RD-2 was 2.00 eV.

A singlet energy S 1 of the compound RD-3 was 2.04 eV.

A singlet energy S 1 of the compound RD-4 was 2.12 eV.

A singlet energy S 1 of the compound CBP was 3.41 eV.

ΔST

T 77K of each of the compounds TADF1 to TADF39 and the comparative compounds 1 to 3 was measured. ΔST was checked from the measurement results of T 77K and the values of the singlet energy S 1 described above.

›Example 39 · 2 of 2

T 77K of each of the compounds TADF1 to TADF39 and the comparative compounds 1 to 3 was measured by the measurement method described above in “Relationship between Triplet Energy and Energy Gap at 77K.”

ΔST of each of each of the compounds TADF1 to TADF39 and the comparative compounds 1 to 3 was less than 0.01 eV.

Main Peak Wavelength of Compounds

A 5-μmol/L toluene solution of each of the compounds (measurement target) was prepared and put in a quartz cell. An emission spectrum (ordinate axis: fluorescence intensity, abscissa axis: wavelength) of each of the samples was measured at a normal temperature (300K). In Examples, the emission spectrum was measured using a spectrophotometer manufactured by Hitachi, Ltd. (device name: F-7000). It should be noted that a fluorescence spectrum measuring device may be different from the above device. A peak wavelength of the fluorescence spectrum exhibiting the maximum luminous intensity was defined as a main peak wavelength.

Results are shown in Table 59.

Measurement results of the compounds RD-1 to RD-4 are as follows.

A main peak wavelength of the compound RD-1 was 609 nm.

A main peak wavelength of the compound RD-2 was 613 nm.

A main peak wavelength of the compound RD-3 was 647 nm.

A main peak wavelength of the compound RD-4 was 585 nm.

Description about Table

“TG1%” represents a 1%-weight loss temperature.

“TG5%” represents a 5%-weight loss temperature.

“−” represents no measurement.

As shown in Table 59, the compounds in Examples where the 1%-weight loss temperature and the 5%-weight loss temperature were measured exhibited lower 1%-weight loss temperature and 5%-weight loss temperature than the comparative compounds 1 to 3 in Comparatives 1 to 3.

In addition, as shown in Table 59, the compounds in Examples where the sublimation temperature was measured exhibited the lower sublimation temperature under high vacuum (10 −5 Pa) than the comparative compounds 1 to 3 in Comparatives 1 to 3.

It was also confirmed that the compounds TADF1 to 6 in Examples 1 to 6 exhibited the lower sublimation temperature under high vacuum (from 1.0×10 −6 Pa to 1.0×10 −3 Pa) than the comparative compounds 1 to 3 in Comparatives 1 to 3.

Manufacturing of Organic EL Device 1

In Example 12A below, an organic EL device was manufactured using the compound (TADF1), as the first compound, in which two groups each represented by the formula (1-1) and two groups each represented by the formula (2-1) were bonded to para-dicyanobenzene.

In Examples 12A-1 and 12A-2, organic EL devices were manufactured using the respective compounds (TADF12, TADF16), as the first compound, in which a single group represented by the formula (1-1) and three groups each represented by the formula (2-1) were bonded to para-dicyanobenzene.

In Comparative 12B, an organic EL device was manufactured using a compound (comparative compound 2) in which four groups each represented by the formula (1-1) were bonded to para-dicyanobenzene.

›Example 12A

A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV/ozone-cleaned for one minute. A film of ITO was set to be 130-nm thick.

After the glass substrate having the transparent electrode line was cleaned, the glass substrate was mounted on a substrate holder of a vacuum evaporation apparatus. Initially, a compound HT-1 and a compound HA were co-deposited on a surface of the glass substrate where the transparent electrode line was provided in a manner to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer. In the hole injecting layer, a concentration of the compound HT-1 was set at 97 mass % and a concentration of the compound HA was set at 3 mass %.

Next, the compound HT-1 was vapor-deposited on the hole injecting layer to form a 200-nm-thick first hole transporting layer on the hole injecting layer.

Next, a compound HT-2 was vapor-deposited on the first hole transporting layer to form a 10-nm-thick second hole transporting layer.

Subsequently, the compound TADF1 (first compound), the compound RD-1 (second compound) and the compound CBP (third compound) were co-deposited on the second hole transporting layer to form a 25-nm-thick emitting layer (first organic layer). A concentration of the compound TADF1 was set at 25 mass %, a concentration of the compound RD-1 was set at 1 mass %, and a concentration of the compound CBP was set at 74 mass % in the emitting layer.

Next, a compound ET-1 was vapor-deposited on the emitting layer to form a 10-nm-thick first electron transporting layer.

Next, a compound ET-2 was vapor-deposited on the first electron transporting layer to form a 30-nm-thick second electron transporting layer.

Next, lithium fluoride (LiF) was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting electrode (cathode).

A metal aluminum (Al) was then vapor-deposited on the electron injecting electrode to form an 80-nm-thick metal Al cathode.

A device arrangement of the organic EL device of Example 12A is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF1:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Numerals in parentheses represent a film thickness (unit: nm).

The numerals (97%:3%) represented by percentage in the same parentheses indicate a ratio (mass %) of the compound HT-1 and the compound HA in the hole injecting layer. The numerals (74%:25%:1%) represented by percentage in the same parentheses indicate a ratio (mass %) of the third compound, the first compound and the second compound in the emitting layer. Hereinafter, the same notation is applied.

›Example 12A-1

The organic EL device in Example 12A-1 was manufactured in the same manner as in Example 12A except that the compound TADF12 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 12A-1 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF12:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

›Example 12A-2

The organic EL device in Example 12A-2 was manufactured in the same manner as in Example 12A except that the compound TADF16 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 12A-2 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF16:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Comparative 12B

The organic EL device in Comparative 12B was manufactured in the same manner as in Example 12A except that the comparative compound 2 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Comparative 12B is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP: Comparative Compound 2:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Evaluation 1-1

The organic EL devices manufactured in Example 12A and Comparative 12B were evaluated as follows. Evaluation results are shown in Table 60.

External Quantum Efficiency EQE Voltage was applied on each of the organic EL devices such that a current density was 0.1 mA/cm 2 or 10 mA/cm 2 where spectral radiance spectra were measured using a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral-radiance spectra, assuming that the spectra were provided under a Lambertian radiation.

Hereinafter, the external quantum efficiency EQE (%) at 0.1 mA/cm 2 of the current density will be referred to as “EQE (%) at a low current.” The external quantum efficiency EQE (%) at 10 mA/cm 2 of the current density will be referred to as “EQE (%) at a high current.”

Provided that “EQE (%) at a low current” in Comparative 12B was 100%, “EQE (%) at a low current” in Example 12A was calculated as “EQE (relative value: %) at a low current” using the following numerical formula (Numerical Formula 100).

EQE (relative value: %) at a low current in Example 12 A =(EQE (%) at a low current in Example 12 A /EQE (%) at a low current in Comparative 12 B )×100 (Numerical Formula 100)

Provided that “EQE (%) at a high current” in Comparative 12B was 100%, “EQE (%) at a high current” in Example 12A was calculated as “EQE (relative value: %) at a high current” using the following numerical formula (Numerical Formula 101).

EQE (relative value: %) at a high current in Example 12 A =(EQE (%) at a high current in Example 12 A /EQE (%) at a high current in Comparative 12 B )×100 (Numerical Formula 101)

Chromaticity CIEx, CIEy, and Main Peak Wavelength λ p

Voltage was applied on each of the organic EL devices such that a current density was 10 mA/cm 2 , where spectral radiance spectra were measured using a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). Chromaticity CIEx, CIEy, and a main peak wavelength λ p (unit: nm) were calculated from the obtained spectral radiance spectra.

Description about Table

The “at a low current” refers to a current whose current density is 1 mA/cm 2 . The “at a high current” refers to a current whose current density is 10 mA/cm 2 . The same is applied to Tables below.

As compared with the organic EL device in Comparative 12B, the organic EL device in Example 12A improved the external quantum efficiency EQE both at the low current (at the current density being 0.1 mA/cm 2 ) and at the high current (at the current density being 10 mA/cm 2 ).

Evaluation 1-2

The organic EL devices manufactured in Examples 12A-1 and 12A-2 and Comparative 12B were evaluated as follows. Evaluation results are shown in Table 61.

External Quantum Efficiency EQE

Provided that “EQE (%) at a low current” in Comparative 12B was 100%, “EQE (%) at a low current” in Example 12A-1 was calculated as “EQE (relative value: %) at a low current” using the same method as that of the organic EL device manufactured in Example 12A. Also with respect to the organic EL device in Example 12A-2, “EQE (relative value: %) at a low current” was obtained using the same method.

Drive Voltage

Voltage (unit: V) when current was applied between the anode and the cathode such that a current density was 10 mA/cm 2 was measured.

Provided that a “drive voltage (V)” in Comparative 12B was 100%, a “drive voltage (V)” in Example 12A-1 was calculated as a “drive voltage (relative value: %)” using the following numerical formula (Numerical Formula 100A). Also with respect to the organic EL device in Example 12A-2, a “drive voltage (relative value: %)” was obtained using the same method.

drive voltage (relative value: %) in Example 12 A -1=(drive voltage ( V ) in Example 12 A -1/drive voltage ( V ) in Comparative 12 B )×100 (Numerical Formula 100A)

Values of Chromaticity CIEx, CIEy, and Main Peak Wavelength λ p

Chromaticity CIEx, CIEy, and a main peak wavelength λ p (unit: nm) were calculated using the same method as that for the organic EL device manufactured in Example 12A.

The organic EL devices in Examples 12A-1 and 12A-2 exhibited a lower drive voltage and a higher external quantum efficiency EQE at a low current (at a current density being 0.1 mA/cm 2 ) than those of the organic EL device in Comparative 12B.

Manufacturing 2 of Organic EL Device 2

In Examples 13A and 13A-1, organic EL devices were manufactured using the respective compounds (TADF7, TADF13), as the first compound, in which two groups each represented by the formula (1-1) and two groups each represented by the formula (2-1) were bonded to meta-dicyanobenzene.

In Comparative 13B, an organic EL device was manufactured using a compound (comparative compound 1) in which four groups each represented by the formula (1-1) were bonded to meta-dicyanobenzene.

›Example 13A

The organic EL device in Example 13A was manufactured in the same manner as in Example 12A except that the compound TADF7 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 13A is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF7:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

›Example 13A-1

The organic EL device in Example 13A-1 was manufactured in the same manner as in Example 12A except that the compound TADF13 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 13A-1 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF13:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Comparative 13B

The organic EL device in Comparative 13B was manufactured in the same manner as in Example 12A except that the comparative compound 1 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Comparative 13B is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP: comparative compound 1:RD-1(25.74%:25%:1%)/ET-1 (10)/ET-2(30)/LiF(1)/Al(80)

Evaluation 2-1

The organic EL devices manufactured in Example 13A and Comparative 13B were evaluated as follows. Evaluation results are shown in Table 62.

Drive Voltage

Voltage (unit: V) when current was applied between the anode and the cathode such that a current density was 10 mA/cm 2 was measured.

Provided that a “drive voltage (V)” in Comparative 13B was 100%, a “drive voltage (V)” in Example 13A was calculated as a “drive voltage (relative value: %)” using the following numerical formula (Numerical Formula 103).

drive voltage (relative value: %) in Example 13 A =(drive voltage ( V ) in Example 13 A /drive voltage ( V ) in Comparative 13 B )×100 (Numerical Formula 103)

Values of Chromaticity CIEx, CIEy, and Main Peak Wavelength λ p

Chromaticity CIEx, CIEy, and a main peak wavelength λ p (unit: nm) were calculated using the same method as that for the organic EL device manufactured in Example 12A.

The organic EL device in Example 13A exhibited a lower drive voltage than that of organic EL device in Comparative 13B.

Evaluation 2-2

The organic EL devices manufactured in Example 13A-1 and Comparative 13B were evaluated as follows. Evaluation results are shown in Table 63.

Drive Voltage

Provided that a “drive voltage (unit: V)” in Comparative 13B was 100%, a “drive voltage (unit: V)” in Example 13A-1 was calculated as a “drive voltage (relative value: %)” using the same method as that of the organic EL device manufactured in Example 12A-1.

Values of Chromaticity CIEx, CIEy, and Main Peak Wavelength λ p

Chromaticity CIEx, CIEy, and a main peak wavelength λ p (unit: nm) were calculated using the same method as that for the organic EL device manufactured in Example 12A.

The organic EL device in Example 13A-1 exhibited a lower drive voltage than that of organic EL device in Comparative 13B.

Manufacturing 3 of Organic EL Device 3

In Example 14A, an organic EL device was manufactured using the compound (TADF6), as the first compound, in which a single group represented by the formula (1-1) and three groups each represented by the formula (2-1) were bonded to ortho-dicyanobenzene.

In Comparative 14B, an organic EL device was manufactured using a compound (comparative compound 3) in which four groups each represented by the formula (1-1) were bonded to ortho-dicyanobenzene.

›Example 14A

The organic EL device in Example 14A was manufactured in the same manner as in Example 12A except that the compound TADF6 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 14A is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF6:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Comparative 14B

The organic EL device in Comparative 14B was manufactured in the same manner as in Example 12A except that the comparative compound 3 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Comparative 14B is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP: Comparative Compound 3:RD-1(25.74%:25%:1%)/ET-1(1%)/ET-2(30)/LiF(1)/Al(80)

Evaluation 3

The organic EL devices manufactured in Example 14A and Comparative 14B were evaluated as follows. Evaluation results are shown in Table 64.

Drive Voltage

Provided that a “drive voltage (unit: V)” in Comparative 14B was 100%, a “drive voltage (unit: V)” in Example 14A was calculated as a “drive voltage (relative value: %)” using the same method as that of the organic EL device manufactured in Example 13A.

External Quantum Efficiency EQE

Provided that “EQE (%) at a low current” in Comparative 14B was 100%, “EQE (%) at a low current” in Example 14A was calculated as “EQE (relative value: %) at a low current” using the same method as that of the organic EL device manufactured in Example 12A.

Chromaticity CIEx, CIEy, and Main Peak Wavelength λ p

Chromaticity CIEx, CIEy, and a main peak wavelength λ p (unit: nm) were calculated using the same method as that for the organic EL device manufactured in Example 12A.

The organic EL device in Example 14A exhibited a lower drive voltage and a higher external quantum efficiency EQE at a low current (at a current density being 0.1 mA/cm 2 ) than those of the organic EL device in Comparative 14B.

Manufacturing 4 of Organic EL Device 4

In Example 15A, an organic EL device was manufactured using the compound (TADF18), as the first compound, in which two groups each represented by the formula (1-4) and two groups each represented by the formula (2-1) were bonded to para-dicyanobenzene.

In Examples 15A-1 and 15A-5, organic EL devices were manufactured using the compounds (TADF20, TADF38), as the first compound, in which a single group represented by the formula (1-1) and three groups each represented by the formula (2-1) were bonded to para-dicyanobenzene.

In Examples 15A-2 and 15A-4, organic EL devices were manufactured using the compounds (TADF22, TADF37), as the first compound, in which a single group represented by the formula (1-4) and three groups each represented by the formula (2-1) were bonded to para-dicyanobenzene.

In Example 15A-3, an organic EL device was manufactured using the compounds (TADF28), as the first compound, in which two groups each represented by the formula (1-2) and two groups each represented by the formula (2-1) were bonded to para-dicyanobenzene.

›Example 15A

The organic EL device in Example 15A was manufactured in the same manner as in Example 12A except that the compound TADF18 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 15A is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF18:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Numerals in parentheses represent a film thickness (unit: nm).

›Example 15A-1

The organic EL device in Example 15A-1 was manufactured in the same manner as in Example 12A except that the compound TADF20 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 15A-1 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF20:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

›Example 15A-2

The organic EL device in Example 15A-2 was manufactured in the same manner as in Example 12A except that the compound TADF22 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 15A-2 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF22:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

›Example 15A-3

The organic EL device in Example 15A-3 was manufactured in the same manner as in Example 12A except that the compound TADF28 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 15A-3 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF28:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

›Example 15A-4

The organic EL device in Example 15A-4 was manufactured in the same manner as in Example 12A except that the compound TADF37 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 15A-4 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF37:RD-1(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

›Example 15A-5

The organic EL device in Comparative 15A-5 was manufactured in the same manner as in Example 12A except that the compound TADF38 was used in place of the compound TADF1 in the emitting layer of Example 12A.

A device arrangement of the organic EL device in Example 15A-5 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF38:RD-1(25.74%:25%: 1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Evaluation 4

The organic EL devices manufactured in Examples 15A and 15A-1 to 15A-5 were evaluated as follows. Evaluation results are shown in Table 65. Evaluation results of Comparative 12B are also shown in Table 65.

External Quantum Efficiency EQE

Provided that “EQE (%) at a low current” in Comparative 12B was 100%, “EQE (%) at a low current” in each of Examples 15A and 15A-1 to 15A-5 was calculated as “EQE (relative value: %) at a low current” using the same method as that of the organic EL device manufactured in Example 12A. Provided that “EQE (%) at a high current” in Comparative 12B was 100%, “EQE (%) at a high current” in each of Examples 15A and 15A-1 to 15A-5 was calculated as “EQE (relative value: %) at a high current.”

Drive Voltage

Provided that a “drive voltage (unit: V)” in Comparative 12B was 100%, a “drive voltage (unit: V)” in each of Examples 15A and 15A-1 to 15A-5 was calculated as a “drive voltage (relative value: %)” using the same method as that of the organic EL device manufactured in Example 13A.

Chromaticity CIEx, CIEy, and Main Peak Wavelength λ p

Chromaticity CIEx, CIEy, and a main peak wavelength λ p (unit: nm) were calculated using the same method as that for the organic EL device manufactured in Example 12A.

As compared with the organic EL device in Comparative 12B, the organic EL devices in Examples 15A-1 to 15A-5 improved the external quantum efficiency EQE both at the low current (at the current density being 0.1 mA/cm 2 ) and at the high current (at the current density being 10 mA/cm 2 ). Further, the organic EL devices of Examples 15A, 15A-1 to 15A-2 and 15A-4 exhibited a lower drive voltage than that of the organic EL device of Comparative 12B.

Manufacturing of Organic EL Device 5

In Examples 16A, 6A-1 and 16A-2, organic EL devices were manufactured using the compound (TADF22), as the first compound, in which a single group represented by the formula (1-4) and three groups each represented by the formula (2-1) were bonded to para-dicyanobenzene.

In Comparatives 16B, 16B-1 and 16B-2, organic EL devices were manufactured using a compound (comparative compound 2) in which four groups each represented by the formula (1-1) were bonded to para-dicyanobenzene.

›Example 16A

Next, the compound HT-1 was vapor-deposited on the hole injecting layer to form a 200-nm-thick first hole transporting layer on the hole injecting layer.

Next, a compound HT-2 was vapor-deposited on the first hole transporting layer to form a 10-nm-thick second hole transporting layer.

Subsequently, the compound TADF22 (first compound), the compound RD-2 (second compound) and the compound CBP (third compound) were co-deposited on the second hole transporting layer to form a 25-nm-thick emitting layer (first organic layer). A concentration of the compound TADF22 was set at 25 mass %, a concentration of the compound RD-2 was set at 1 mass %, and a concentration of the compound CBP was set at 74 mass % in the emitting layer.

Next, a compound ET-1 was vapor-deposited on the emitting layer to form a 10-nm-thick first electron transporting layer.

Next, a compound ET-2 was vapor-deposited on the first electron transporting layer to form a 30-nm-thick second electron transporting layer.

Next, lithium fluoride (LiF) was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting electrode (cathode).

A metal aluminum (Al) was then vapor-deposited on the electron injecting electrode to form an 80-nm-thick metal Al cathode.

A device arrangement of the organic EL device in Example 16A is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:TADF22:RD-2(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Numerals in parentheses represent a film thickness (unit: nm).

›Example 16A-1

The organic EL device in Example 16A-1 was manufactured in the same manner as in Example 16A except that the compound RD-3 was used in place of the compound RD-2 in the emitting layer of Example 16A.

A device arrangement of the organic EL device in Example 16A-1 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP: TADF22:RD-3(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

›Example 16A-2

The organic EL device in Example 16A-2 was manufactured in the same manner as in Example 16A except that the compound RD-4 was used in place of the compound RD-2 in the emitting layer of Example 16A.

A device arrangement of the organic EL device in Example 16A-2 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP: TADF22:RD-4(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Comparative 16B

The organic EL device in Comparative 16B was manufactured in the same manner as in Example 16A except that the comparative compound 2 was used in place of the compound TADF22 in the emitting layer of Example 16A.

A device arrangement of the organic EL device in Example 16B is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP: comparative compound 2:RD-2(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Comparative 16B-1

The organic EL device in Comparative 16B-1 was manufactured in the same manner as in Example 16A-1 except that the comparative compound 2 was used in place of the compound TADF22 in the emitting layer of Example 16A-1.

A device arrangement of the organic EL device in Example 16B-1 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP: comparative compound 2: RD-3(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Comparative 16B-2

The organic EL device in Comparative 16B-2 was manufactured in the same manner as in Example 16A-2 except that the comparative compound 2 was used in place of the compound TADF22 in the emitting layer of Example 16A-2.

A device arrangement of the organic EL device in Example 16B-2 is roughly shown as follows.

ITO(130)/HT-1:HA(10.97%:3%)/HT-1(200)/HT-2(10)/CBP:Comparative Compound 2:RD-4(25.74%:25%:1%)/ET-1(10)/ET-2(30)/LiF(1)/Al(80)

Evaluation 5

The organic EL devices manufactured in Examples 16A, 16A-1 and 16A-2 and Comparatives 16B, 16B-1 and 16B-2 were evaluated as follows. Evaluation results are shown in Table 66.

External Quantum Efficiency EQE

Provided that “EQE (%) at a low current” in each of Comparatives 16B, 16B-1 and 16B-2 was 100%, “EQE (%) at a low current” in each of Examples 16A, 16A-1 and 16-2 was calculated as “EQE (relative value: %) at a low current” using the same method as that of the organic EL device manufactured in Example 12A. Provided that “EQE (%) at a high current” in each of Comparatives 16B, 16B-1 and 16B-2 was 100%, “EQE (%) at a high current” in each of Examples in each of Examples 16A, 16A-1 and 16-2 was calculated as “EQE (relative value: %) at a high current.”

Drive Voltage

Provided that a “drive voltage (unit: V)” in each of Comparatives 16B, 16B-1 and 16B-2 was 100%, a “drive voltage (unit: V)” in each of Examples 16A, 16A-1 and 16-2 was calculated as a “drive voltage (relative value: %)” using the same method as that of the organic EL device manufactured in Example 13A.

Chromaticity CIEx, CIEy, and Main Peak Wavelength λ p

Chromaticity CIEx, CIEy, and a main peak wavelength λ p (unit: nm) were calculated using the same method as that for the organic EL device manufactured in Example 12A.

As compared with the organic EL device in Comparative 16B, the organic EL device in Example 16A improved the external quantum efficiency EQE both at the low current (at the current density being 0.1 mA/cm 2 ) and at the high current (at the current density being 10 mA/cm 2 ) and exhibited a lower drive voltage.

As compared with the organic EL device in Comparative 16B-1, the organic EL device in Example 16A-1 improved the external quantum efficiency EQE both at the low current (at the current density being 0.1 mA/cm 2 ) and at the high current (at the current density being 10 mA/cm 2 ) and exhibited a lower drive voltage.

As compared with the organic EL device in Comparative 16B-2, the organic EL device in Example 16A-2 improved the external quantum efficiency EQE both at the low current (at the current density being 0.1 mA/cm 2 ) and at the high current (at the current density being 10 mA/cm 2 ) and exhibited a lower drive voltage.

›Tables in the description — 64

TABLE 1

Compound No.	Type	Formula No.	D 1A	D 1B	D 2A	D 2B
Compound 1	Compound 1a	(11-1)	1	1	1′	1′
	Compound 1b	(12-1)	1	1	1′	1′
	Compound 1c	(12-2)	1	1	1′	1′
	Compound 1d	(13-1)	1	1	1′	1′
	Compound 1e	(13-2)	1	1	1′	1′

TABLE 2

Compound No.	Type	Formula No.
Compound X	Compound Xa	(11-1)
	Compound Xb	(12-1)
	Compound Xc	(12-2)
	Compound Xd	(13-1)
	Compound Xe	(13-2)

TABLE 3

Compound No	D 1A	D 1B	D 2A	D 2B
Compound 1	1	1	1′	1′
Compound 2	2	2	1′	1′
Compound 3	3	3	1′	1′
Compound 4	4	4	1′	1′
Compound 5	5	5	1′	1′
Compound 6	6	6	1′	1′
Compound 7	7	7	1′	1′
Compound 8	8	8	1′	1′
Compound 9	9	9	1′	1′
Compound 10	10	10	1′	1′
Compound 11	11	11	1′	1′
Compound 12	12	12	1′	1′
Compound 13	13	13	1′	1′
Compound 14	14	14	1′	1′
Compound 15	15	15	1′	1′
Compound 16	16	16	1′	1′
Compound 17	17	17	1′	1′
Compound 18	18	18	1′	1′
Compound 19	19	19	1′	1′
Compound 20	20	20	1′	1′
Compound 21	21	21	1′	1′
Compound 22	22	22	1′	1′
Compound 23	23	23	1′	1′
Compound 24	24	24	1′	1′
Compound 25	25	25	1′	1′
Compound 26	26	26	1′	1′
Compound 27	27	27	1′	1′
Compound 28	28	28	1′	1′
Compound 29	29	29	1′	1′
Compound 30	30	30	1′	1′
Compound 31	31	31	1′	1′
Compound 32	32	32	1′	1′
Compound 33	33	33	1′	1′
Compound 34	34	34	1′	1′
Compound 35	35	35	1′	1′
Compound 36	36	36	1′	1′

TABLE 4

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 37	1	1	2′	2′
Compound 38	2	2	2′	2′
Compound 39	3	3	2′	2′
Compound 40	4	4	2′	2′
Compound 41	5	5	2′	2′
Compound 42	6	6	2′	2′
Compound 43	7	7	2′	2′
Compound 44	8	8	2′	2′
Compound 45	9	9	2′	2′
Compound 46	10	10	2′	2′
Compound 47	11	11	2′	2′
Compound 48	12	12	2′	2′
Compound 49	13	13	2′	2′
Compound 50	14	14	2′	2′
Compound 51	15	15	2′	2′
Compound 52	16	16	2′	2′
Compound 53	17	17	2′	2′
Compound 54	18	18	2′	2′
Compound 55	19	19	2′	2′
Compound 56	20	20	2′	2′
Compound 57	21	21	2′	2′
Compound 58	22	22	2′	2′
Compound 59	23	23	2′	2′
Compound 60	24	24	2′	2′
Compound 61	25	25	2′	2′
Compound 62	26	26	2′	2′
Compound 63	27	27	2′	2′
Compound 64	28	28	2′	2′
Compound 65	29	29	2′	2′
Compound 66	30	30	2′	2′
Compound 67	31	31	2′	2′
Compound 68	32	32	2′	2′
Compound 69	33	33	2′	2′
Compound 70	34	34	2′	2′
Compound 71	35	35	2′	2′
Compound 72	36	36	2′	2′

TABLE 5

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 73	1	1	3′	3′
Compound 74	2	2	3′	3′
Compound 75	3	3	3′	3′
Compound 76	4	4	3′	3′
Compound 77	5	5	3′	3′
Compound 78	6	6	3′	3′
Compound 79	7	7	3′	3′
Compound 80	8	8	3′	3′
Compound 81	9	9	3′	3′
Compound 82	10	10	3′	3′
Compound 83	11	11	3′	3′
Compound 84	12	12	3′	3′
Compound 85	13	13	3′	3′
Compound 86	14	14	3′	3′
Compound 87	15	15	3′	3′
Compound 88	16	16	3′	3′
Compound 89	17	17	3′	3′
Compound 90	18	18	3′	3′
Compound 91	19	19	3′	3′
Compound 92	20	20	3′	3′
Compound 93	21	21	3′	3′
Compound 94	22	22	3′	3′
Compound 95	23	23	3′	3′
Compound 96	24	24	3′	3′
Compound 97	25	25	3′	3′
Compound 98	26	26	3′	3′
Compound 99	27	27	3′	3′
Compound 100	28	28	3′	3′
Compound 101	29	29	3′	3′
Compound 102	30	30	3′	3′
Compound 103	31	31	3′	3′
Compound 104	32	32	3′	3′
Compound 105	33	33	3′	3′
Compound 106	34	34	3′	3′
Compound 107	35	35	3′	3′
Compound 108	36	36	3′	3′

TABLE 6

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 109	1	1	4′	4′
Compound 110	2	2	4′	4′
Compound 111	3	3	4′	4′
Compound 112	4	4	4′	4′
Compound 113	5	5	4′	4′
Compound 114	6	6	4′	4′
Compound 115	7	7	4′	4′
Compound 116	8	8	4′	4′
Compound 117	9	9	4′	4′
Compound 118	10	10	4′	4′
Compound 119	11	11	4′	4′
Compound 120	12	12	4′	4′
Compound 121	13	13	4′	4′
Compound 122	14	14	4′	4′
Compound 123	15	15	4′	4′
Compound 124	16	16	4′	4′
Compound 125	17	17	4′	4′
Compound 126	18	18	4′	4′
Compound 127	19	19	4′	4′
Compound 128	20	20	4′	4′
Compound 129	21	21	4′	4′
Compound 130	22	22	4′	4′
Compound 131	23	23	4′	4′
Compound 132	24	24	4′	4′
Compound 133	25	25	4′	4′
Compound 134	26	26	4′	4′
Compound 135	27	27	4′	4′
Compound 136	28	28	4′	4′
Compound 137	29	29	4′	4′
Compound 138	30	30	4′	4′
Compound 139	31	31	4′	4′
Compound 140	32	32	4′	4′
Compound 141	33	33	4′	4′
Compound 142	34	34	4′	4′
Compound 143	35	35	4′	4′
Compound 144	36	36	4′	4′

TABLE 7

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 145	1	1	5′	5′
Compound 146	2	2	5′	5′
Compound 147	3	3	5′	5′
Compound 148	4	4	5′	5′
Compound 149	5	5	5′	5′
Compound 150	6	6	5′	5′
Compound 151	7	7	5′	5′
Compound 152	8	8	5′	5′
Compound 153	9	9	5′	5′
Compound 154	10	10	5′	5′
Compound 155	11	11	5′	5′
Compound 156	12	12	5′	5′
Compound 157	13	13	5′	5′
Compound 158	14	14	5′	5′
Compound 159	15	15	5′	5′
Compound 160	16	16	5′	5′
Compound 161	17	17	5′	5′
Compound 162	18	18	5′	5′
Compound 163	19	19	5′	5′
Compound 164	20	20	5′	5′
Compound 165	21	21	5′	5′
Compound 166	22	22	5′	5′
Compound 167	23	23	5′	5′
Compound 168	24	24	5′	5′
Compound 169	25	25	5′	5′
Compound 170	26	26	5′	5′
Compound 171	27	27	5′	5′
Compound 172	28	28	5′	5′
Compound 173	29	29	5′	5′
Compound 174	30	30	5′	5′
Compound 175	31	31	5′	5′
Compound 176	32	32	5′	5′
Compound 177	33	33	5′	5′
Compound 178	34	34	5′	5′
Compound 179	35	35	5′	5′
Compound 180	36	36	5′	5′

TABLE 8

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 181	1	1	6′	6′
Compound 182	2	2	6′	6′
Compound 183	3	3	6′	6′
Compound 184	4	4	6′	6′
Compound 185	5	5	6′	6′
Compound 186	6	6	6′	6′
Compound 187	7	7	6′	6′
Compound 188	8	8	6′	6′
Compound 189	9	9	6′	6′
Compound 190	10	10	6′	6′
Compound 191	11	11	6′	6′
Compound 192	12	12	6′	6′
Compound 193	13	13	6′	6′
Compound 194	14	14	6′	6′
Compound 195	15	15	6′	6′
Compound 196	16	16	6′	6′
Compound 197	17	17	6′	6′
Compound 198	18	18	6′	6′
Compound 199	19	19	6′	6′
Compound 200	20	20	6′	6′
Compound 201	21	21	6′	6′
Compound 202	22	22	6′	6′
Compound 203	23	23	6′	6′
Compound 204	24	24	6′	6′
Compound 205	25	25	6′	6′
Compound 206	26	26	6′	6′
Compound 207	27	27	6′	6′
Compound 208	28	28	6′	6′
Compound 209	29	29	6′	6′
Compound 210	30	30	6′	6′
Compound 211	31	31	6′	6′
Compound 212	32	32	6′	6′
Compound 213	33	33	6′	6′
Compound 214	34	34	6′	6′
Compound 215	35	35	6′	6′
Compound 216	36	36	6′	6′

TABLE 9

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 217	1	1	7′	7′
Compound 218	2	2	7′	7′
Compound 219	3	3	7′	7′
Compound 220	4	4	7′	7′
Compound 221	5	5	7′	7′
Compound 222	6	6	7′	7′
Compound 223	7	7	7′	7′
Compound 224	8	8	7′	7
Compound 225	9	9	7′	7′
Compound 226	10	10	7′	7′
Compound 227	11	11	7′	7′
Compound 228	12	12	7′	7′
Compound 229	13	13	7′	7′
Compound 230	14	14	7′	7′
Compound 231	15	15	7′	7′
Compound 232	16	16	7′	7′
Compound 233	17	17	7′	7′
Compound 234	18	18	7′	7′
Compound 235	19	19	7′	7′
Compound 236	20	20	7′	7′
Compound 237	21	21	7′	7′
Compound 238	22	22	7′	7′
Compound 239	23	23	7′	7′
Compound 240	24	24	7′	7′
Compound 241	25	25	7′	7′
Compound 242	26	26	7′	7′
Compound 243	27	27	7′	7′
Compound 244	28	28	7′	7′
Compound 245	29	29	7′	7′
Compound 246	30	30	7′	7′
Compound 247	31	31	7′	7′
Compound 248	32	32	7′	7′
Compound 249	33	33	7′	7′
Compound 250	34	34	7′	7′
Compound 251	35	35	7′	7′
Compound 252	36	36	7′	7′

TABLE 10

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 253	1	1	8′	8′
Compound 254	2	2	8′	8′
Compound 255	3	3	8′	8′
Compound 256	4	4	8′	8′
Compound 257	5	5	8′	8′
Compound 258	6	6	8′	8′
Compound 259	7	7	8′	8′
Compound 260	8	8	8′	8′
Compound 261	9	9	8′	8′
Compound 262	10	10	8′	8′
Compound 263	11	11	8′	8′
Compound 264	12	12	8′	8′
Compound 265	13	13	8′	8′
Compound 266	14	14	8′	8′
Compound 267	15	15	8′	8′
Compound 268	16	16	8′	8′
Compound 269	17	17	8′	8′
Compound 270	18	18	8′	8′
Compound 271	19	19	8′	8′
Compound 272	20	20	8′	8′
Compound 273	21	21	8′	8′
Compound 274	22	22	8′	8′
Compound 275	23	23	8′	8′
Compound 276	24	24	8′	8′
Compound 277	25	25	8′	8′
Compound 278	26	26	8′	8′
Compound 279	27	27	8′	8′
Compound 280	28	28	8′	8′
Compound 281	29	29	8′	8′
Compound 282	30	30	8′	8′
Compound 283	31	31	8′	8′
Compound 284	32	32	8′	8′
Compound 285	33	33	8′	8′
Compound 286	34	34	8′	8′
Compound 287	35	35	8′	8′
Compound 288	36	36	8′	8′

TABLE 11

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 289	1	1	9′	9′
Compound 290	2	2	9′	9′
Compound 291	3	3	9′	9′
Compound 292	4	4	9′	9′
Compound 293	5	5	9′	9′
Compound 294	6	6	9′	9′
Compound 295	7	7	9′	9′
Compound 296	8	8	9′	9′
Compound 297	9	9	9′	9′
Compound 298	10	10	9′	9′
Compound 299	11	11	9′	9′
Compound 300	12	12	9′	9′
Compound 301	13	13	9′	9′
Compound 302	14	14	9′	9′
Compound 303	15	15	9′	9′
Compound 304	16	16	9′	9′
Compound 305	17	17	9′	9′
Compound 306	18	18	9′	9′
Compound 307	19	19	9′	9′
Compound 308	20	20	9′	9′
Compound 309	21	21	9′	9′
Compound 310	22	22	9′	9′
Compound 311	23	23	9′	9′
Compound 312	24	24	9′	9′
Compound 313	25	25	9′	9′
Compound 314	26	26	9′	9′
Compound 315	27	27	9′	9′
Compound 316	28	28	9′	9′
Compound 317	29	29	9′	9′
Compound 318	30	30	9′	9′
Compound 319	31	31	9′	9′
Compound 320	32	32	9′	9′
Compound 321	33	33	9′	9′
Compound 322	34	34	9′	9′
Compound 323	35	35	9′	9′
Compound 324	36	36	9′	9′

TABLE 12

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 325	1	1	10′	10′
Compound 326	2	2	10′	10′
Compound 327	3	3	10′	10′
Compound 328	4	4	10′	10′
Compound 329	5	5	10′	10′
Compound 330	6	6	10′	10′
Compound 331	7	7	10′	10′
Compound 332	8	8	10′	10′
Compound 333	9	9	10′	10′
Compound 334	10	10	10′	10′
Compound 335	11	11	10′	10′
Compound 336	12	12	10′	10′
Compound 337	13	13	10′	10′
Compound 338	14	14	10′	10′
Compound 339	15	15	10′	10′
Compound 340	16	16	10′	10′
Compound 341	17	17	10′	10′
Compound 342	18	18	10′	10′
Compound 343	19	19	10′	10′
Compound 344	20	20	10′	10′
Compound 345	21	21	10′	10′
Compound 346	22	22	10′	10′
Compound 347	23	23	10′	10′
Compound 348	24	24	10′	10′
Compound 349	25	25	10′	10′
Compound 350	26	26	10′	10′
Compound 351	27	27	10′	10′
Compound 352	28	28	10′	10′
Compound 353	29	29	10′	10′
Compound 354	30	30	10′	10′
Compound 355	31	31	10′	10′
Compound 356	32	32	10′	10′
Compound 357	33	33	10′	10′
Compound 358	34	34	10′	10′
Compound 359	35	35	10′	10′
Compound 360	36	36	10′	10′

TABLE 13

Compound No	D 1A	D 1B	D 2A	D 2B
Compound 361	1	1	11′	11′
Compound 362	2	2	11′	11′
Compound 363	3	3	11′	11′
Compound 364	4	4	11′	11′
Compound 365	5	5	11′	11′
Compound 366	6	6	11′	11′
Compound 367	7	7	11′	11′
Compound 368	8	8	11′	11′
Compound 369	9	9	11′	11′
Compound 370	10	10	11′	11′
Compound 371	11	11	11′	11′
Compound 372	12	12	11′	11′
Compound 373	13	13	11′	11′
Compound 374	14	14	11′	11′
Compound 375	15	15	11′	11′
Compound 376	16	16	11′	11′
Compound 377	17	17	11′	11′
Compound 378	18	18	11′	11′
Compound 379	19	19	11′	11′
Compound 380	20	20	11′	11′
Compound 381	21	21	11′	11′
Compound 382	22	22	11′	11′
Compound 383	23	23	11′	11′
Compound 384	24	24	11′	11′
Compound 385	25	25	11′	11′
Compound 386	26	26	11′	11′
Compound 387	27	27	11′	11′
Compound 388	28	28	11′	11′
Compound 389	29	29	11′	11′
Compound 390	30	30	11′	11′
Compound 391	31	31	11′	11′
Compound 392	32	32	11′	11′
Compound 393	33	33	11′	11′
Compound 394	34	34	11′	11′
Compound 395	35	35	11′	11′
Compound 396	36	36	11′	11′

TABLE 14

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 397	1	1	12′	12′
Compound 398	2	2	12′	12′
Compound 399	3	3	12′	12′
Compound 400	4	4	12′	12′
Compound 401	5	5	12′	12′
Compound 402	6	6	12′	12′
Compound 403	7	7	12′	12′
Compound 404	8	8	12′	12′
Compound 405	9	9	12′	12′
Compound 406	10	10	12′	12′
Compound 407	11	11	12′	12′
Compound 408	12	12	12′	12′
Compound 409	13	13	12′	12′
Compound 410	14	14	12′	12′
Compound 411	15	15	12′	12′
Compound 412	16	16	12′	12′
Compound 413	17	17	12′	12′
Compound 414	18	18	12′	12′
Compound 415	19	19	12′	12′
Compound 416	20	20	12′	12′
Compound 417	21	21	12′	12′
Compound 418	22	22	12′	12′
Compound 419	23	23	12′	12′
Compound 420	24	24	12′	12′
Compound 421	25	25	12′	12′
Compound 422	26	26	12′	12′
Compound 423	27	27	12′	12′
Compound 424	28	28	12′	12′
Compound 425	29	29	12′	12′
Compound 426	30	30	12′	12′
Compound 427	31	31	12′	12′
Compound 428	32	32	12′	12′
Compound 429	33	33	12′	12′
Compound 430	34	34	12′	12′
Compound 431	35	35	12′	12′
Compound 432	36	36	12′	12′

TABLE 15

Compound No	D 1A	D 1B	D 2A	D 2B
Compound 433	1	1	13′	13′
Compound 434	2	2	13′	13′
Compound 435	3	3	13′	13′
Compound 436	4	4	13′	13′
Compound 437	5	5	13′	13′
Compound 438	6	6	13′	13′
Compound 439	7	7	13′	13′
Compound 440	8	8	13′	13′
Compound 441	9	9	13′	13′
Compound 442	10	10	13′	13′
Compound 443	11	11	13′	13′
Compound 444	12	12	13′	13′
Compound 445	13	13	13′	13′
Compound 446	14	14	13′	13′
Compound 447	15	15	13′	13′
Compound 448	16	16	13′	13′
Compound 449	17	17	13′	13′
Compound 450	18	18	13′	13′
Compound 451	19	19	13′	13′
Compound 452	20	20	13′	13′
Compound 453	21	21	13′	13′
Compound 454	22	22	13′	13′
Compound 455	23	23	13′	13′
Compound 456	24	24	13′	13′
Compound 457	25	25	13′	13′
Compound 458	26	26	13′	13′
Compound 459	27	27	13′	13′
Compound 460	28	28	13′	13′
Compound 461	29	29	13′	13′
Compound 462	30	30	13′	13′
Compound 463	31	31	13′	13′
Compound 464	32	32	13′	13′
Compound 465	33	33	13′	13′
Compound 466	34	34	13′	13′
Compound 467	35	35	13′	13′
Compound 468	36	36	13′	13′

TABLE 16

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 469	1	1	14′	14′
Compound 470	2	2	14′	14′
Compound 471	3	3	14′	14′
Compound 472	4	4	14′	14′
Compound 473	5	5	14′	14′
Compound 474	6	6	14′	14′
Compound 475	7	7	14′	14′
Compound 476	8	8	14′	14′
Compound 477	9	9	14′	14′
Compound 478	10	10	14′	14′
Compound 479	11	11	14′	14′
Compound 480	12	12	14′	14′
Compound 481	13	13	14′	14′
Compound 482	14	14	14′	14′
Compound 483	15	15	14′	14′
Compound 484	16	16	14′	14′
Compound 485	17	17	14′	14′
Compound 486	18	18	14′	14′
Compound 487	19	19	14′	14′
Compound 488	20	20	14′	14′
Compound 489	21	21	14′	14′
Compound 490	22	22	14′	14′
Compound 491	23	23	14′	14′
Compound 492	24	24	14′	14′
Compound 493	25	25	14′	14′
Compound 494	26	26	14′	14′
Compound 495	27	27	14′	14′
Compound 496	28	28	14′	14′
Compound 497	29	29	14′	14′
Compound 498	30	30	14′	14′
Compound 499	31	31	14′	14′
Compound 500	32	32	14′	14′
Compound 501	33	33	14′	14′
Compound 502	34	34	14′	14′
Compound 503	35	35	14′	14′
Compound 504	36	36	14′	14′

TABLE 17

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 505	1	1	15′	15′
Compound 506	2	2	15′	15′
Compound 507	3	3	15′	15′
Compound 508	4	4	15′	15′
Compound 509	5	5	15′	15′
Compound 510	6	6	15′	15′
Compound 511	7	7	15′	15′
Compound 512	8	8	15′	15′
Compound 513	9	9	15′	15′
Compound 514	10	10	15′	15′
Compound 515	11	11	15′	15′
Compound 516	12	12	15′	15′
Compound 517	13	13	15′	15′
Compound 518	14	14	15′	15′
Compound 519	15	15	15′	15′
Compound 520	16	16	15′	15′
Compound 521	17	17	15′	15′
Compound 522	18	18	15′	15′
Compound 523	19	19	15′	15′
Compound 524	20	20	15′	15′
Compound 525	21	21	15′	15′
Compound 526	22	22	15′	15′
Compound 527	23	23	15′	15′
Compound 528	24	24	15′	15′
Compound 529	25	25	15′	15′
Compound 530	26	26	15′	15′
Compound 531	27	27	15′	15′
Compound 532	28	28	15′	15′
Compound 533	29	29	15′	15′
Compound 534	30	30	15′	15′
Compound 535	31	31	15′	15′
Compound 536	32	32	15′	15′
Compound 537	33	33	15′	15′
Compound 538	34	34	15′	15′
Compound 539	35	35	15′	15′
Compound 540	36	36	15′	15′

TABLE 18

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 1621	1	1	16′	16′
Compound 1622	2	2	16′	16′
Compound 1623	3	3	16′	16′
Compound 1624	4	4	16′	16′
Compound 1625	5	5	16′	16′
Compound 1626	6	6	16′	16′
Compound 1627	7	7	16′	16′
Compound 1628	8	8	16′	16′
Compound 1629	9	9	16′	16′
Compound 1630	10	10	16′	16′
Compound 1631	11	11	16′	16′
Compound 1632	12	12	16′	16′
Compound 1633	13	13	16′	16′
Compound 1634	14	14	16′	16′
Compound 1635	15	15	16′	16′
Compound 1636	16	16	16′	16′
Compound 1637	17	17	16′	16′
Compound 1638	18	18	16′	16′
Compound 1639	19	19	16′	16′
Compound 1640	20	20	16′	16′
Compound 1641	21	21	16′	16′
Compound 1642	22	22	16′	16′
Compound 1643	23	23	16′	16′
Compound 1644	24	24	16′	16′
Compound 1645	25	25	16′	16′
Compound 1646	26	26	16′	16′
Compound 1647	27	27	16′	16′
Compound 1648	28	28	16′	16′
Compound 1649	29	29	16′	16′
Compound 1650	30	30	16′	16′
Compound 1651	31	31	16′	16′
Compound 1652	32	32	16′	16′
Compound 1653	33	33	16′	16′
Compound 1654	34	34	16′	16′
Compound 1655	35	35	16′	16′
Compound 1656	36	36	16′	16′

TABLE 19

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 1657	1	1	17′	17′
Compound 1658	2	2	17′	17′
Compound 1659	3	3	17′	17′
Compound 1660	4	4	17′	17′
Compound 1661	5	5	17′	17′
Compound 1662	6	6	17′	17′
Compound 1663	7	7	17′	17′
Compound 1664	8	8	17′	17′
Compound 1665	9	9	17′	17′
Compound 1666	10	10	17′	17′
Compound 1667	11	11	17′	17′
Compound 1668	12	12	17′	17′
Compound 1669	13	13	17′	17′
Compound 1670	14	14	17′	17′
Compound 1671	15	15	17′	17′
Compound 1672	16	16	17′	17′
Compound 1673	17	17	17′	17′
Compound 1674	18	18	17′	17′
Compound 1675	19	19	17′	17′
Compound 1676	20	20	17′	17′
Compound 1677	21	21	17′	17′
Compound 1678	22	22	17′	17′
Compound 1679	23	23	17′	17′
Compound 1680	24	24	17′	17′
Compound 1681	25	25	17′	17′
Compound 1682	26	26	17′	17′
Compound 1683	27	27	17′	17′
Compound 1684	28	28	17′	17′
Compound 1685	29	29	17′	17′
Compound 1686	30	30	17′	17′
Compound 1687	31	31	17′	17′
Compound 1688	32	32	17′	17′
Compound 1689	33	33	17′	17′
Compound 1690	34	34	17′	17′
Compound 1691	35	35	17′	17′
Compound 1692	36	36	17′	17′

TABLE 20

Compound No.	D 1A	D 1B	D 2A	D 2B
Compound 1693	1	1	18′	18′
Compound 1694	2	2	18′	18′
Compound 1695	3	3	18′	18′
Compound 1696	4	4	18′	18′
Compound 1697	5	5	18′	18′
Compound 1698	6	6	18′	18′
Compound 1699	7	7	18′	18′
Compound 1700	8	8	18′	18′
Compound 1701	9	9	18′	18′
Compound 1702	10	10	18′	18′
Compound 1703	11	11	18′	18′
Compound 1704	12	12	18′	18′
Compound 1705	13	13	18′	18′
Compound 1706	14	14	18′	18′
Compound 1707	15	15	18′	18′
Compound 1708	16	16	18′	18′
Compound 1709	17	17	18′	18′
Compound 1710	18	18	18′	18′
Compound 1711	19	19	18′	18′
Compound 1712	20	20	18′	18′
Compound 1713	21	21	18′	18′
Compound 1714	22	22	18′	18′
Compound 1715	23	23	18′	18′
Compound 1716	24	24	18′	18′
Compound 1717	25	25	18′	18′
Compound 1718	26	26	18′	18′
Compound 1719	27	27	18′	18′
Compound 1720	28	28	18′	18′
Compound 1721	29	29	18′	18′
Compound 1722	30	30	18′	18′
Compound 1723	31	31	18′	18′
Compound 1724	32	32	18′	18′
Compound 1725	33	33	18′	18′
Compound 1726	34	34	18′	18′
Compound 1727	35	35	18′	18′
Compound 1728	36	36	18′	18′

TABLE 21

Compound No.	Type	Formula No.
Compound Y	Compound Ya	(12-3)
	Compound Yb	(13-3)
	Compound Yc	(12-4)
	Compound Yd	(12-5)
	Compound Ye	(11-2)

TABLE 22

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 541	1	1′	1′	1′
Compound 542	2	1′	1′	1′
Compound 543	3	1′	1′	1′
Compound 544	4	1′	1′	1′
Compound 545	5	1′	1′	1′
Compound 546	6	1′	1′	1′
Compound 547	7	1′	1′	1′
Compound 548	8	1′	1′	1′
Compound 549	9	1′	1′	1′
Compound 550	10	1′	1′	1′
Compound 551	11	1′	1′	1′
Compound 552	12	1′	1′	1′
Compound 553	13	1′	1′	1′
Compound 554	14	1′	1′	1′
Compound 555	15	1′	1′	1′
Compound 556	16	1′	1′	1′
Compound 557	17	1′	1′	1′
Compound 558	18	1′	1′	1′
Compound 559	19	1′	1′	1′
Compound 560	20	1′	1′	1′
Compound 561	21	1′	1′	1′
Compound 562	22	1′	1′	1′
Compound 563	23	1′	1′	1′
Compound 564	24	1′	1′	1′
Compound 565	25	1′	1′	1′
Compound 566	26	1′	1′	1′
Compound 567	27	1′	1′	1′
Compound 568	28	1′	1′	1′
Compound 569	29	1′	1′	1′
Compound 570	30	1′	1′	1′
Compound 571	31	1′	1′	1′
Compound 572	32	1′	1′	1′
Compound 573	33	1′	1′	1′
Compound 574	34	1′	1′	1′
Compound 575	35	1′	1′	1′
Compound 576	36	1′	1′	1′

TABLE 23

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 577	1	2′	2′	2′
Compound 578	2	2′	2′	2′
Compound 579	3	2′	2′	2′
Compound 580	4	2′	2′	2′
Compound 581	5	2′	2′	2′
Compound 582	6	2′	2′	2′
Compound 583	7	2′	2′	2′
Compound 584	8	2′	2′	2′
Compound 585	9	2′	2′	2′
Compound 586	10	2′	2′	2′
Compound 587	11	2′	2′	2′
Compound 588	12	2′	2′	2′
Compound 589	13	2′	2′	2′
Compound 590	14	2′	2′	2′
Compound 591	15	2′	2′	2′
Compound 592	16	2′	2′	2′
Compound 593	17	2′	2′	2′
Compound 594	18	2′	2′	2′
Compound 595	19	2′	2′	2′
Compound 596	20	2′	2′	2′
Compound 597	21	2′	2′	2′
Compound 598	22	2′	2′	2′
Compound 599	23	2′	2′	2′
Compound 600	24	2′	2′	2′
Compound 601	25	2′	2′	2′
Compound 602	26	2′	2′	2′
Compound 603	27	2′	2′	2′
Compound 604	28	2′	2′	2′
Compound 605	29	2′	2′	2′
Compound 606	30	2′	2′	2′
Compound 607	31	2′	2′	2′
Compound 608	32	2′	2′	2′
Compound 609	33	2′	2′	2′
Compound 610	34	2′	2′	2′
Compound 611	35	2′	2′	2′
Compound 612	36	2′	2′	2′

TABLE 24

Compound No	D 1A	D 2A	D 2B	D 2C
Compound 613	1	3′	3′	3′
Compound 614	2	3′	3′	3′
Compound 615	3	3′	3′	3′
Compound 616	4	3′	3′	3′
Compound 617	5	3′	3′	3′
Compound 618	6	3′	3′	3′
Compound 619	7	3′	3′	3′
Compound 620	8	3′	3′	3′
Compound 621	9	3′	3′	3′
Compound 622	10	3′	3′	3′
Compound 623	11	3′	3′	3′
Compound 624	12	3′	3′	3′
Compound 625	13	3′	3′	3′
Compound 626	14	3′	3′	3′
Compound 627	15	3′	3′	3′
Compound 628	16	3′	3′	3′
Compound 629	17	3′	3′	3′
Compound 630	18	3′	3′	3′
Compound 631	19	3′	3′	3′
Compound 632	20	3′	3′	3′
Compound 633	21	3′	3′	3′
Compound 634	22	3′	3′	3′
Compound 635	23	3′	3′	3′
Compound 636	24	3′	3′	3′
Compound 637	25	3′	3′	3′
Compound 638	26	3′	3′	3′
Compound 639	27	3′	3′	3′
Compound 640	28	3′	3′	3′
Compound 641	29	3′	3′	3′
Compound 642	30	3′	3′	3′
Compound 643	31	3′	3′	3′
Compound 644	32	3′	3′	3′
Compound 645	33	3′	3′	3′
Compound 646	34	3′	3′	3′
Compound 647	35	3′	3′	3′
Compound 648	36	3′	3′	3′

TABLE 25

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 649	1	4′	4′	4′
Compound 650	2	4′	4′	4′
Compound 651	3	4′	4′	4′
Compound 652	4	4′	4′	4′
Compound 653	5	4′	4′	4′
Compound 654	6	4′	4′	4′
Compound 655	7	4′	4′	4′
Compound 656	8	4′	4′	4′
Compound 657	9	4′	4′	4′
Compound 658	10	4′	4′	4′
Compound 659	11	4′	4′	4′
Compound 660	12	4′	4′	4′
Compound 661	13	4′	4′	4′
Compound 662	14	4′	4′	4′
Compound 663	15	4′	4′	4′
Compound 664	16	4′	4′	4′
Compound 665	17	4′	4′	4′
Compound 666	18	4′	4′	4′
Compound 667	19	4′	4′	4′
Compound 668	20	4′	4′	4′
Compound 669	21	4′	4′	4′
Compound 670	22	4′	4′	4′
Compound 671	23	4′	4′	4′
Compound 672	24	4′	4′	4′
Compound 673	25	4′	4′	4′
Compound 674	26	4′	4′	4′
Compound 675	27	4′	4′	4′
Compound 676	28	4′	4′	4′
Compound 677	29	4′	4′	4′
Compound 678	30	4′	4′	4′
Compound 679	31	4′	4′	4′
Compound 680	32	4′	4′	4′
Compound 681	33	4′	4′	4′
Compound 682	34	4′	4′	4′
Compound 683	35	4′	4′	4′
Compound 684	36	4′	4′	4′

TABLE 26

Compound No	D 1A	D 2A	D 2B	D 2C
Compound 685	1	5′	5′	5′
Compound 686	2	5′	5′	5′
Compound 687	3	5′	5′	5′
Compound 688	4	5′	5′	5′
Compound 689	5	5′	5′	5′
Compound 690	6	5′	5′	5′
Compound 691	7	5′	5′	5′
Compound 692	8	5′	5′	5′
Compound 693	9	5′	5′	5′
Compound 694	10	5′	5′	5′
Compound 695	11	5′	5′	5′
Compound 696	12	5′	5′	5′
Compound 697	13	5′	5′	5′
Compound 698	14	5′	5′	5′
Compound 699	15	5′	5′	5′
Compound 700	16	5′	5′	5′
Compound 701	17	5′	5′	5′
Compound 702	18	5′	5′	5′
Compound 703	19	5′	5′	5′
Compound 704	20	5′	5′	5′
Compound 705	21	5′	5′	5′
Compound 706	22	5′	5′	5′
Compound 707	23	5′	5′	5′
Compound 708	24	5′	5′	5′
Compound 709	25	5′	5′	5′
Compound 710	26	5′	5′	5′
Compound 711	27	5′	5′	5′
Compound 712	28	5′	5′	5′
Compound 713	29	5′	5′	5′
Compound 714	30	5′	5′	5′
Compound 715	31	5′	5′	5′
Compound 716	32	5′	5′	5′
Compound 717	33	5′	5′	5′
Compound 718	34	5′	5′	5′
Compound 719	35	5′	5′	5′
Compound 720	36	5′	5′	5′

TABLE 27

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 721	1	6′	6′	6′
Compound 722	2	6′	6′	6′
Compound 723	3	6′	6′	6′
Compound 724	4	6′	6′	6′
Compound 725	5	6′	6′	6′
Compound 726	6	6′	6′	6′
Compound 727	7	6′	6′	6′
Compound 728	8	6′	6′	6′
Compound 729	9	6′	6′	6′
Compound 730	10	6′	6′	6′
Compound 731	11	6′	6′	6′
Compound 732	12	6′	6′	6′
Compound 733	13	6′	6′	6′
Compound 734	14	6′	6′	6′
Compound 735	15	6′	6′	6′
Compound 736	16	6′	6′	6′
Compound 737	17	6′	6′	6′
Compound 738	18	6′	6′	6′
Compound 739	19	6′	6′	6′
Compound 740	20	6′	6′	6′
Compound 741	21	6′	6′	6′
Compound 742	22	6′	6′	6′
Compound 743	23	6′	6′	6′
Compound 744	24	6′	6′	6′
Compound 745	25	6′	6′	6′
Compound 746	26	6′	6′	6′
Compound 747	27	6′	6′	6′
Compound 748	28	6′	6′	6′
Compound 749	29	6′	6′	6′
Compound 750	30	6′	6′	6′
Compound 751	31	6′	6′	6′
Compound 752	32	6′	6′	6′
Compound 753	33	6′	6′	6′
Compound 754	34	6′	6′	6′
Compound 755	35	6′	6′	6′
Compound 756	36	6′	6′	6′

TABLE 28

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 757	1	7′	7′	7′
Compound 758	2	7′	7′	7′
Compound 759	3	7′	7′	7′
Compound 760	4	7′	7′	7′
Compound 761	5	7′	7′	7′
Compound 762	6	7′	7′	7′
Compound 763	7	7′	7′	7′
Compound 764	8	7′	7′	7′
Compound 765	9	7′	7′	7′
Compound 766	10	7′	7′	7′
Compound 767	11	7′	7′	7′
Compound 768	12	7′	7′	7′
Compound 769	13	7′	7′	7′
Compound 770	14	7′	7′	7′
Compound 771	15	7′	7′	7′
Compound 772	16	7′	7′	7′
Compound 773	17	7′	7′	7′
Compound 774	18	7′	7′	7′
Compound 775	19	7′	7′	7′
Compound 776	20	7′	7′	7′
Compound 777	21	7′	7′	7′
Compound 778	22	7′	7′	7′
Compound 779	23	7′	7′	7′
Compound 780	24	7′	7′	7′
Compound 781	25	7′	7′	7′
Compound 782	26	7′	7′	7′
Compound 783	27	7′	7′	7′
Compound 784	28	7′	7′	7′
Compound 785	29	7′	7′	7′
Compound 786	30	7′	7′	7′
Compound 787	31	7′	7′	7′
Compound 788	32	7′	7′	7′
Compound 789	33	7′	7′	7′
Compound 790	34	7′	7′	7′
Compound 791	35	7′	7′	7′
Compound 792	36	7′	7′	7′

TABLE 29

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 793	1	8′	8′	8′
Compound 794	2	8′	8′	8′
Compound 795	3	8′	8′	8′
Compound 796	4	8′	8′	8′
Compound 797	5	8′	8′	8′
Compound 798	6	8′	8′	8′
Compound 799	7	8′	8′	8′
Compound 800	8	8′	8′	8′
Compound 801	9	8′	8′	8′
Compound 802	10	8′	8′	8′
Compound 803	11	8′	8′	8′
Compound 804	12	8′	8′	8′
Compound 805	13	8′	8′	8′
Compound 806	14	8′	8′	8′
Compound 807	15	8′	8′	8′
Compound 808	16	8′	8′	8′
Compound 809	17	8′	8′	8′
Compound 810	18	8′	8′	8′
Compound 811	19	8′	8′	8′
Compound 812	20	8′	8′	8′
Compound 813	21	8′	8′	8′
Compound 814	22	8′	8′	8′
Compound 815	23	8′	8′	8′
Compound 816	24	8′	8′	8′
Compound 817	25	8′	8′	8′
Compound 818	26	8′	8′	8′
Compound 819	27	8′	8′	8′
Compound 820	28	8′	8′	8′
Compound 821	29	8′	8′	8′
Compound 822	30	8′	8′	8′
Compound 823	31	8′	8′	8′
Compound 824	32	8′	8′	8′
Compound 825	33	8′	8′	8′
Compound 826	34	8′	8′	8′
Compound 827	35	8′	8′	8′
Compound 828	36	8′	8′	8′

TABLE 30

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 829	1	9′	9′	9′
Compound 830	2	9′	9′	9′
Compound 831	3	9′	9′	9′
Compound 832	4	9′	9	9′
Compound 833	5	9′	9′	9′
Compound 834	6	9′	9′	9′
Compound 835	7	9′	9′	9′
Compound 836	8	9′	9′	9′
Compound 837	9	9′	9′	9′
Compound 838	10	9′	9′	9′
Compound 839	11	9′	9′	9′
Compound 840	12	9′	9′	9′
Compound 841	13	9′	9′	9′
Compound 842	14	9′	9′	9′
Compound 843	15	9′	9′	9′
Compound 844	16	9′	9′	9′
Compound 845	17	9′	9′	9′
Compound 846	18	9′	9′	9′
Compound 847	19	9′	9′	9′
Compound 848	20	9′	9′	9′
Compound 849	21	9′	9′	9′
Compound 850	22	9′	9′	9′
Compound 851	23	9′	9′	9′
Compound 852	24	9′	9′	9′
Compound 853	25	9′	9′	9′
Compound 854	26	9′	9′	9′
Compound 855	27	9′	9′	9′
Compound 856	28	9′	9′	9′
Compound 857	29	9′	9′	9′
Compound 858	30	9′	9′	9′
Compound 859	31	9′	9′	9′
Compound 860	32	9′	9′	9′
Compound 861	33	9′	9′	9′
Compound 862	34	9′	9′	9′
Compound 863	35	9′	9′	9′
Compound 864	36	9′	9′	9′

TABLE 31

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 865	1	10′	10′	10′
Compound 866	2	10′	10′	10′
Compound 867	3	10′	10′	10′
Compound 868	4	10′	10′	10′
Compound 869	5	10′	10′	10′
Compound 870	6	10′	10′	10′
Compound 871	7	10′	10′	10′
Compound 872	8	10′	10′	10′
Compound 873	9	10′	10′	10′
Compound 874	10	10′	10′	10′
Compound 875	11	10′	10′	10′
Compound 876	12	10′	10′	10′
Compound 877	13	10′	10′	10′
Compound 878	14	10′	10′	10′
Compound 879	15	10′	10′	10′
Compound 880	16	10′	10′	10′
Compound 881	17	10′	10′	10′
Compound 882	18	10′	10′	10′
Compound 883	19	10′	10′	10′
Compound 884	20	10′	10′	10′
Compound 885	21	10′	10′	10′
Compound 886	22	10′	10′	10′
Compound 887	23	10′	10′	10′
Compound 888	24	10′	10′	10′
Compound 889	25	10′	10′	10′
Compound 890	26	10′	10′	10′
Compound 891	27	10′	10′	10′
Compound 892	28	10′	10′	10′
Compound 893	29	10′	10′	10′
Compound 894	30	10′	10′	10′
Compound 895	31	10′	10′	10′
Compound 896	32	10′	10′	10′
Compound 897	33	10′	10′	10′
Compound 898	34	10′	10′	10′
Compound 899	35	10′	10′	10′
Compound 900	36	10′	10′	10′

TABLE 32

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 901	1	11′	11′	11′
Compound 902	2	11′	11′	11′
Compound 903	3	11′	11′	11′
Compound 904	4	11′	11′	11′
Compound 905	5	11′	11′	11′
Compound 906	6	11′	11′	11′
Compound 907	7	11′	11′	11′
Compound 908	8	11′	11′	11′
Compound 909	9	11′	11′	11′
Compound 910	10	11′	11′	11′
Compound 911	11	11′	11′	11′
Compound 912	12	11′	11′	11′
Compound 913	13	11′	11′	11′
Compound 914	14	11′	11′	11′
Compound 915	15	11′	11′	11′
Compound 916	16	11′	11′	11′
Compound 917	17	11′	11′	11′
Compound 918	18	11′	11′	11′
Compound 919	19	11′	11′	11′
Compound 920	20	11′	11′	11′
Compound 921	21	11′	11′	11′
Compound 922	22	11′	11′	11′
Compound 923	23	11′	11′	11′
Compound 924	24	11′	11′	11
Compound 925	25	11′	11′	11′
Compound 926	26	11′	11′	11′
Compound 927	27	11′	11′	11′
Compound 928	28	11′	11′	11′
Compound 929	29	11′	11′	11′
Compound 930	30	11′	11′	11′
Compound 931	31	11′	11′	11′
Compound 932	32	11′	11′	11′
Compound 933	33	11′	11′	11′
Compound 934	34	11′	11′	11′
Compound 935	35	11′	11′	11′
Compound 936	36	11′	11′	11′

TABLE 33

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 937	1	12′	12′	12′
Compound 938	2	12′	12′	12′
Compound 939	3	12′	12′	12′
Compound 940	4	12′	12′	12′
Compound 941	5	12′	12′	12′
Compound 942	6	12′	12′	12′
Compound 943	7	12′	12′	12′
Compound 944	8	12′	12′	12′
Compound 945	9	12′	12′	12′
Compound 946	10	12′	12′	12′
Compound 947	11	12′	12′	12′
Compound 948	12	12′	12′	12′
Compound 949	13	12′	12′	12′
Compound 950	14	12′	12′	12′
Compound 951	15	12′	12′	12′
Compound 952	16	12′	12′	12′
Compound 953	17	12′	12′	12′
Compound 954	18	12′	12′	12′
Compound 955	19	12′	12′	12′
Compound 956	20	12′	12′	12′
Compound 957	21	12′	12′	12′
Compound 958	22	12′	12′	12′
Compound 959	23	12′	12′	12′
Compound 960	24	12′	12′	12′
Compound 961	25	12′	12′	12′
Compound 962	26	12′	12′	12′
Compound 963	27	12′	12′	12′
Compound 964	28	12′	12′	12′
Compound 965	29	12′	12′	12′
Compound 966	30	12′	12′	12′
Compound 967	31	12′	12′	12′
Compound 968	32	12′	12′	12′
Compound 969	33	12′	12′	12′
Compound 970	34	12′	12′	12′
Compound 971	35	12′	12′	12′
Compound 972	36	12′	12′	12′

TABLE 34

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 973	1	13′	13′	13′
Compound 974	2	13′	13′	13′
Compound 975	3	13′	13′	13′
Compound 976	4	13′	13′	13′
Compound 977	5	13′	13′	13′
Compound 978	6	13′	13′	13′
Compound 979	7	13′	13′	13′
Compound 980	8	13′	13′	13′
Compound 981	9	13′	13′	13′
Compound 982	10	13′	13′	13′
Compound 983	11	13′	13′	13′
Compound 984	12	13′	13′	13′
Compound 985	13	13′	13′	13′
Compound 986	14	13	13′	13′
Compound 987	15	13′	13′	13′
Compound 988	16	13′	13′	13′
Compound 989	17	13′	13′	13′
Compound 990	18	13′	13′	13′
Compound 991	19	13′	13′	13′
Compound 992	20	13′	13′	13′
Compound 993	21	13′	13′	13′
Compound 994	22	13′	13′	13′
Compound 995	23	13′	13′	13′
Compound 996	24	13′	13′	13′
Compound 997	25	13′	13′	13′
Compound 998	26	13′	13′	13′
Compound 999	27	13′	13′	13′
Compound 1000	28	13′	13′	13′
Compound 1001	29	13′	13′	13′
Compound 1002	30	13′	13′	13′
Compound 1003	31	13′	13′	13′
Compound 1004	32	13′	13′	13′
Compound 1005	33	13′	13′	13′
Compound 1006	34	13′	13′	13′
Compound 1007	35	13′	13′	13′
Compound 1008	36	13′	13′	13′

TABLE 35

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 1009	1	14′	14′	14′
Compound 1010	2	14′	14′	14′
Compound 1011	3	14′	14′	14′
Compound 1012	4	14′	14′	14′
Compound 1013	5	14′	14′	14′
Compound 1014	6	14′	14′	14′
Compound 1015	7	14′	14′	14′
Compound 1016	8	14′	14′	14′
Compound 1017	9	14′	14′	14′
Compound 1018	10	14′	14′	14′
Compound 1019	11	14′	14′	14′
Compound 1020	12	14′	14′	14′
Compound 1021	13	14′	14′	14′
Compound 1022	14	14′	14′	14′
Compound 1023	15	14′	14′	14′
Compound 1024	16	14′	14′	14′
Compound 1025	17	14′	14′	14′
Compound 1026	18	14′	14′	14′
Compound 1027	19	14′	14′	14′
Compound 1028	20	14′	14′	14′
Compound 1029	21	14′	14′	14′
Compound 1030	22	14′	14′	14′
Compound 1031	23	14′	14′	14′
Compound 1032	24	14′	14′	14′
Compound 1033	25	14′	14′	14′
Compound 1034	26	14′	14′	14′
Compound 1035	27	14′	14′	14′
Compound 1036	28	14′	14′	14′
Compound 1037	29	14′	14′	14′
Compound 1038	30	14′	14′	14′
Compound 1039	31	14′	14′	14′
Compound 1040	32	14′	14′	14′
Compound 1041	33	14′	14′	14′
Compound 1042	34	14′	14′	14′
Compound 1043	35	14′	14′	14′
Compound 1044	36	14′	14′	14′

TABLE 36

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 1045	1	15′	15′	15′
Compound 1046	2	15′	15′	15′
Compound 1047	3	15′	15′	15′
Compound 1048	4	15′	15′	15′
Compound 1049	5	15′	15′	15′
Compound 1050	6	15′	15′	15′
Compound 1051	7	15′	15′	15′
Compound 1052	8	15′	15′	15′
Compound 1053	9	15′	15′	15′
Compound 1054	10	15′	15′	15′
Compound 1055	11	15′	15′	15′
Compound 1056	12	15′	15′	15′
Compound 1057	13	15′	15′	15′
Compound 1058	14	15′	15′	15′
Compound 1059	15	15′	15′	15′
Compound 1060	16	15′	15′	15′
Compound 1061	17	15′	15′	15′
Compound 1062	18	15′	15′	15′
Compound 1063	19	15′	15′	15′
Compound 1064	20	15′	15′	15′
Compound 1065	21	15′	15′	15′
Compound 1066	22	15′	15′	15′
Compound 1067	23	15′	15′	15′
Compound 1068	24	15′	15′	15′
Compound 1069	25	15′	15′	15′
Compound 1070	26	15′	15′	15′
Compound 1071	27	15′	15′	15′
Compound 1072	28	15′	15′	15′
Compound 1073	29	15′	15′	15′
Compound 1074	30	15′	15′	15′
Compound 1075	31	15′	15′	15′
Compound 1076	32	15′	15′	15′
Compound 1077	33	15′	15′	15′
Compound 1078	34	15′	15′	15′
Compound 1079	35	15′	15′	15′
Compound 1080	36	15′	15′	15′

TABLE 37

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 1729	1	16′	16′	16′
Compound 1730	2	16′	16′	16′
Compound 1731	3	16′	16′	16′
Compound 1732	4	16′	16′	16′
Compound 1733	5	16′	16′	16′
Compound 1734	6	16′	16′	16′
Compound 1735	7	16′	16′	16′
Compound 1736	8	16′	16′	16′
Compound 1737	9	16′	16′	16′
Compound 1738	10	16′	16′	16′
Compound 1739	11	16′	16′	16′
Compound 1740	12	16′	16′	16′
Compound 1741	13	16′	16′	16′
Compound 1742	14	16′	16′	16′
Compound 1743	15	16′	16′	16′
Compound 1744	16	16′	16′	16′
Compound 1745	17	16′	16′	16′
Compound 1746	18	16′	16′	16′
Compound 1747	19	16′	16′	16′
Compound 1748	20	16′	16′	16′
Compound 1749	21	16′	16′	16′
Compound 1750	22	16′	16′	16′
Compound 1751	23	16′	16′	16′
Compound 1752	24	16′	16′	16′
Compound 1753	25	16′	16′	16′
Compound 1754	26	16′	16′	16′
Compound 1755	27	16′	16′	16′
Compound 1756	28	16′	16′	16′
Compound 1757	29	16′	16′	16′
Compound 1758	30	16′	16′	16′
Compound 1759	31	16′	16′	16′
Compound 1760	32	16′	16′	16′
Compound 1761	33	16′	16′	16′
Compound 1762	34	16′	16′	16′
Compound 1763	35	16′	16′	16′
Compound 1764	36	16′	16′	16′

TABLE 38

Compound No	D 1A	D 2A	D 2B	D 2C
Compound 1765	1	17′	17′	17′
Compound 1766	2	17′	17′	17′
Compound 1767	3	17′	17′	17′
Compound 1768	4	17′	17′	17′
Compound 1769	5	17′	17′	17′
Compound 1770	6	17′	17′	17′
Compound 1771	7	17′	17′	17′
Compound 1772	8	17′	17′	17′
Compound 1773	9	17′	17′	17′
Compound 1774	10	17′	17′	17′
Compound 1775	11	17′	17′	17′
Compound 1776	12	17′	17′	17′
Compound 1777	13	17′	17′	17′
Compound 1778	14	17′	17′	17′
Compound 1779	15	17′	17′	17′
Compound 1780	16	17′	17′	17′
Compound 1781	17	17′	17′	17′
Compound 1782	18	17′	17′	17′
Compound 1783	19	17′	17′	17′
Compound 1784	20	17′	17′	17′
Compound 1785	21	17′	17′	17′
Compound 1786	22	17′	17′	17′
Compound 1787	23	17′	17′	17′
Compound 1788	24	17′	17′	17′
Compound 1789	25	17′	17′	17′
Compound 1790	26	17′	17′	17′
Compound 1791	27	17′	17′	17′
Compound 1792	28	17′	17′	17′
Compound 1793	29	17′	17′	17′
Compound 1794	30	17′	17′	17′
Compound 1795	31	17′	17′	17′
Compound 1796	32	17′	17′	17′
Compound 1797	33	17′	17′	17′
Compound 1798	34	17′	17′	17′
Compound 1799	35	17′	17′	17′
Compound 1800	36	17′	17′	17′

TABLE 39

Compound No.	D 1A	D 2A	D 2B	D 2C
Compound 1801	1	18′	18′	18′
Compound 1802	2	18′	18′	18′
Compound 1803	3	18′	18′	18′
Compound 1804	4	18′	18′	18′
Compound 1805	5	18′	18′	18′
Compound 1806	6	18′	18′	18′
Compound 1807	7	18′	18′	18′
Compound 1808	8	18′	18′	18′
Compound 1809	9	18′	18′	18′
Compound 1810	10	18′	18′	18′
Compound 1811	11	18′	18′	18′
Compound 1812	12	18′	18′	18′
Compound 1813	13	18′	18′	18′
Compound 1814	14	18′	18′	18′
Compound 1815	15	18′	18′	18′
Compound 1816	16	18′	18′	18′
Compound 1817	17	18′	18′	18′
Compound 1818	18	18′	18′	18′
Compound 1819	19	18′	18′	18′
Compound 1820	20	18′	18′	18′
Compound 1821	21	18′	18′	18′
Compound 1822	22	18′	18′	18′
Compound 1823	23	18′	18′	18′
Compound 1824	24	18′	18′	18′
Compound 1825	25	18′	18′	18′
Compound 1826	26	18′	18′	18′
Compound 1827	27	18′	18′	18′
Compound 1828	28	18′	18′	18′
Compound 1829	29	18′	18′	18′
Compound 1830	30	18′	18′	18′
Compound 1831	31	18′	18′	18′
Compound 1832	32	18′	18′	18′
Compound 1833	33	18′	18′	18′
Compound 1834	34	18′	18′	18′
Compound 1835	35	18′	18′	18′
Compound 1836	36	18′	18′	18′

TABLE 40

Compound No.	Type	Formula No.
Compound Z	Compound Za	(12-6)
	Compound Zb	(13-4)

TABLE 41

Compound No	D 1A	D 1B	D 1C	D 2A
Compound 1081	1	1	1	1′
Compound 1082	2	2	2	1′
Compound 1083	3	3	3	1′
Compound 1084	4	4	4	1′
Compound 1085	5	5	5	1′
Compound 1086	6	6	6	1′
Compound 1087	7	7	7	1′
Compound 1088	8	8	8	1′
Compound 1089	9	9	9	1′
Compound 1090	10	10	10	1′
Compound 1091	11	11	11	1′
Compound 1092	12	12	12	1′
Compound 1093	13	13	13	1′
Compound 1094	14	14	14	1′
Compound 1095	15	15	15	1′
Compound 1096	16	16	16	1′
Compound 1097	17	17	17	1′
Compound 1098	18	18	18	1′
Compound 1099	19	19	19	1′
Compound 1100	20	20	20	1′
Compound 1101	21	21	21	1′
Compound 1102	22	22	22	1′
Compound 1103	23	23	23	1′
Compound 1104	24	24	24	1′
Compound 1105	25	25	25	1′
Compound 1106	26	26	26	1′
Compound 1107	27	27	27	1′
Compound 1108	28	28	28	1′
Compound 1109	29	29	29	1′
Compound 1110	30	30	30	1′
Compound 1111	31	31	31	1′
Compound 1112	32	32	32	1′
Compound 1113	33	33	33	1′
Compound 1114	34	34	34	1′
Compound 1115	35	35	35	1′
Compound 1116	36	36	36	1′

TABLE 42

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1117	1	1	1	2′
Compound 1118	2	2	2	2′
Compound 1119	3	3	3	2′
Compound 1120	4	4	4	2′
Compound 1121	5	5	5	2′
Compound 1122	6	6	6	2′
Compound 1123	7	7	7	2′
Compound 1124	8	8	8	2′
Compound 1125	9	9	9	2′
Compound 1126	10	10	10	2′
Compound 1127	11	11	11	2′
Compound 1128	12	12	12	2′
Compound 1129	13	13	13	2′
Compound 1130	14	14	14	2′
Compound 1131	15	15	15	2′
Compound 1132	16	16	16	2′
Compound 1133	17	17	17	2′
Compound 1134	18	18	18	2′
Compound 1135	19	19	19	2′
Compound 1136	20	20	20	2′
Compound 1137	21	21	21	2′
Compound 1138	22	22	22	2′
Compound 1139	23	23	23	2′
Compound 1140	24	24	24	2′
Compound 1141	25	25	25	2′
Compound 1142	26	26	26	2′
Compound 1143	27	27	27	2′
Compound 1144	28	28	28	2′
Compound 1145	29	29	29	2′
Compound 1146	30	30	30	2′
Compound 1147	31	31	31	2′
Compound 1148	32	32	32	2′
Compound 1149	33	33	33	2′
Compound 1150	34	34	34	2′
Compound 1151	35	35	35	2′
Compound 1152	36	36	36	2′

TABLE 43

Compound No	D 1A	D 1B	D 1C	D 2A
Compound 1153	1	1	1	3′
Compound 1154	2	2	2	3′
Compound 1155	3	3	3	3′
Compound 1156	4	4	4	3′
Compound 1157	5	5	5	3′
Compound 1158	6	6	6	3′
Compound 1159	7	7	7	3′
Compound 1160	8	8	8	3′
Compound 1161	9	9	9	3′
Compound 1162	10	10	10	3′
Compound 1163	11	11	11	3′
Compound 1164	12	12	12	3′
Compound 1165	13	13	13	3′
Compound 1166	14	14	14	3′
Compound 1167	15	15	15	3′
Compound 1168	16	16	16	3′
Compound 1169	17	17	17	3′
Compound 1170	18	18	18	3′
Compound 1171	19	19	19	3′
Compound 1172	20	20	20	3′
Compound 1173	21	21	21	3′
Compound 1174	22	22	22	3′
Compound 1175	23	23	23	3′
Compound 1176	24	24	24	3′
Compound 1177	25	25	25	3′
Compound 1178	26	26	26	3′
Compound 1179	27	27	27	3′
Compound 1180	28	28	28	3′
Compound 1181	29	29	29	3′
Compound 1182	30	30	30	3′
Compound 1183	31	31	31	3′
Compound 1184	32	32	32	3′
Compound 1185	33	33	33	3′
Compound 1186	34	34	34	3′
Compound 1187	35	35	35	3′
Compound 1188	36	36	36	3′

TABLE 44

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1189	1	1	1	4′
Compound 1190	2	2	2	4′
Compound 1191	3	3	3	4′
Compound 1192	4	4	4	4′
Compound 1193	5	5	5	4′
Compound 1194	6	6	6	4′
Compound 1195	7	7	7	4′
Compound 1196	8	8	8	4′
Compound 1197	9	9	9	4′
Compound 1198	10	10	10	4′
Compound 1199	11	11	11	4′
Compound 1200	12	12	12	4′
Compound 1201	13	13	13	4′
Compound 1202	14	14	14	4′
Compound 1203	15	15	15	4′
Compound 1204	16	16	16	4′
Compound 1205	17	17	17	4′
Compound 1206	18	18	18	4′
Compound 1207	19	19	19	4′
Compound 1208	20	20	20	4′
Compound 1209	21	21	21	4′
Compound 1210	22	22	22	4′
Compound 1211	23	23	23	4′
Compound 1212	24	24	24	4′
Compound 1213	25	25	25	4′
Compound 1214	26	26	26	4′
Compound 1215	27	27	27	4′
Compound 1216	28	28	28	4′
Compound 1217	29	29	29	4′
Compound 1218	30	30	30	4′
Compound 1219	31	31	31	4′
Compound 1220	32	32	32	4′
Compound 1221	33	33	33	4′
Compound 1222	34	34	34	4′
Compound 1223	35	35	35	4′
Compound 1224	36	36	36	4′

TABLE 45

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1225	1	1	1	5′
Compound 1226	2	2	2	5′
Compound 1227	3	3	3	5′
Compound 1228	4	4	4	5′
Compound 1229	5	5	5	5′
Compound 1230	6	6	6	5′
Compound 1231	7	7	7	5′
Compound 1232	8	8	8	5′
Compound 1233	9	9	9	5′
Compound 1234	10	10	10	5′
Compound 1235	11	11	11	5′
Compound 1236	12	12	12	5′
Compound 1237	13	13	13	5′
Compound 1238	14	14	14	5′
Compound 1239	15	15	15	5′
Compound 1240	16	16	16	5′
Compound 1241	17	17	17	5′
Compound 1242	18	18	18	5′
Compound 1243	19	19	19	5′
Compound 1244	20	20	20	5′
Compound 1245	21	21	21	5′
Compound 1246	22	22	22	5′
Compound 1247	23	23	23	5′
Compound 1248	24	24	24	5′
Compound 1249	25	25	25	5′
Compound 1250	26	26	26	5′
Compound 1251	27	27	27	5′
Compound 1252	28	28	28	5′
Compound 1253	29	29	29	5′
Compound 1254	30	30	30	5′
Compound 1255	31	31	31	5′
Compound 1256	32	32	32	5′
Compound 1257	33	33	33	5′
Compound 1258	34	34	34	5′
Compound 1259	35	35	35	5′
Compound 1260	36	36	36	5′

TABLE 46

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1261	1	1	1	6′
Compound 1262	2	2	2	6′
Compound 1263	3	3	3	6′
Compound 1264	4	4	4	6′
Compound 1265	5	5	5	6′
Compound 1266	6	6	6	6′
Compound 1267	7	7	7	6′
Compound 1268	8	8	8	6′
Compound 1269	9	9	9	6′
Compound 1270	10	10	10	6′
Compound 1271	11	11	11	6′
Compound 1272	12	12	12	6′
Compound 1273	13	13	13	6′
Compound 1274	14	14	14	6′
Compound 1275	15	15	15	6′
Compound 1276	16	16	16	6′
Compound 1277	17	17	17	6′
Compound 1278	18	18	18	6′
Compound 1279	19	19	19	6′
Compound 1280	20	20	20	6′
Compound 1281	21	21	21	6′
Compound 1282	22	22	22	6′
Compound 1283	23	23	23	6′
Compound 1284	24	24	24	6′
Compound 1285	25	25	25	6′
Compound 1286	26	26	26	6′
Compound 1287	27	27	27	6′
Compound 1288	28	28	28	6′
Compound 1289	29	29	29	6′
Compound 1290	30	30	30	6′
Compound 1291	31	31	31	6′
Compound 1292	32	32	32	6′
Compound 1293	33	33	33	6′
Compound 1294	34	34	34	6′
Compound 1295	35	35	35	6′
Compound 1296	36	36	36	6′

TABLE 47

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1297	1	1	1	7′
Compound 1298	2	2	2	7′
Compound 1299	3	3	3	7′
Compound 1300	4	4	4	7′
Compound 1301	5	5	5	7′
Compound 1302	6	6	6	7′
Compound 1303	7	7	7	7′
Compound 1304	8	8	8	7′
Compound 1305	9	9	9	7′
Compound 1306	10	10	10	7′
Compound 1307	11	11	11	7′
Compound 1308	12	12	12	7′
Compound 1309	13	13	13	7′
Compound 1310	14	14	14	7′
Compound 1311	15	15	15	7′
Compound 1312	16	16	16	7′
Compound 1313	17	17	17	7′
Compound 1314	18	18	18	7′
Compound 1315	19	19	19	7′
Compound 1316	20	20	20	7′
Compound 1317	21	21	21	7′
Compound 1318	22	22	22	7′
Compound 1319	23	23	23	7′
Compound 1320	24	24	24	7′
Compound 1321	25	25	25	7′
Compound 1322	26	26	26	7′
Compound 1323	27	27	27	7′
Compound 1324	28	28	28	7′
Compound 1325	29	29	29	7′
Compound 1326	30	30	30	7′
Compound 1327	31	31	31	7′
Compound 1328	32	32	32	7′
Compound 1329	33	33	33	7′
Compound 1330	34	34	34	7′
Compound 1331	35	35	35	7′
Compound 1332	36	36	36	7′

TABLE 48

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1333	1	1	1	8′
Compound 1334	2	2	2	8′
Compound 1335	3	3	3	8′
Compound 1336	4	4	4	8′
Compound 1337	5	5	5	8′
Compound 1338	6	6	6	8′
Compound 1339	7	7	7	8′
Compound 1340	8	8	8	8′
Compound 1341	9	9	9	8′
Compound 1342	10	10	10	8′
Compound 1343	11	11	11	8′
Compound 1344	12	12	12	8′
Compound 1345	13	13	13	8′
Compound 1346	14	14	14	8′
Compound 1347	15	15	15	8′
Compound 1348	16	16	16	8′
Compound 1349	17	17	17	8′
Compound 1350	18	18	18	8′
Compound 1351	19	19	19	8′
Compound 1352	20	20	20	8′
Compound 1353	21	21	21	8′
Compound 1354	22	22	22	8′
Compound 1355	23	23	23	8′
Compound 1356	24	24	24	8′
Compound 1357	25	25	25	8′
Compound 1358	26	26	26	8′
Compound 1359	27	27	27	8′
Compound 1360	28	28	28	8′
Compound 1361	29	29	29	8′
Compound 1362	30	30	30	8′
Compound 1363	31	31	31	8′
Compound 1364	32	32	32	8′
Compound 1365	33	33	33	8′
Compound 1366	34	34	34	8′
Compound 1367	35	35	35	8′
Compound 1368	36	36	36	8′

TABLE 49

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1369	1	1	1	9′
Compound 1370	2	2	2	9′
Compound 1371	3	3	3	9′
Compound 1372	4	4	4	9′
Compound 1373	5	5	5	9′
Compound 1374	6	6	6	9′
Compound 1375	7	7	7	9′
Compound 1376	8	8	8	9′
Compound 1377	9	9	9	9′
Compound 1378	10	10	10	9′
Compound 1379	11	11	11	9′
Compound 1380	12	12	12	9′
Compound 1381	13	13	13	9′
Compound 1382	14	14	14	9′
Compound 1383	15	15	15	9′
Compound 1384	16	16	16	9′
Compound 1385	17	17	17	9′
Compound 1386	18	18	18	9′
Compound 1387	19	19	19	9′
Compound 1388	20	20	20	9′
Compound 1389	21	21	21	9′
Compound 1390	22	22	22	9′
Compound 1391	23	23	23	9′
Compound 1392	24	24	24	9′
Compound 1393	25	25	25	9′
Compound 1394	26	26	26	9′
Compound 1395	27	27	27	9′
Compound 1396	28	28	28	9′
Compound 1397	29	29	29	9′
Compound 1398	30	30	30	9′
Compound 1399	31	31	31	9′
Compound 1400	32	32	32	9′
Compound 1401	33	33	33	9′
Compound 1402	34	34	34	9′
Compound 1403	35	35	35	9′
Compound 1404	36	36	36	9′

TABLE 50

Compound No	D 1A	D 1B	D 1C	D 2A
Compound 1405	1	1	1	10′
Compound 1406	2	2	2	10′
Compound 1407	3	3	3	10′
Compound 1408	4	4	4	10′
Compound 1409	5	5	5	10′
Compound 1410	6	6	6	10′
Compound 1411	7	7	7	10′
Compound 1412	8	8	8	10′
Compound 1413	9	9	9	10′
Compound 1414	10	10	10	10′
Compound 1415	11	11	11	10′
Compound 1416	12	12	12	10′
Compound 1417	13	13	13	10′
Compound 1418	14	14	14	10′
Compound 1419	15	15	15	10′
Compound 1420	16	16	16	10′
Compound 1421	17	17	17	10′
Compound 1422	18	18	18	10′
Compound 1423	19	19	19	10′
Compound 1424	20	20	20	10′
Compound 1425	21	21	21	10′
Compound 1426	22	22	22	10′
Compound 1427	23	23	23	10′
Compound 1428	24	24	24	10′
Compound 1429	25	25	25	10′
Compound 1430	26	26	26	10′
Compound 1431	27	27	27	10′
Compound 1432	28	28	28	10′
Compound 1433	29	29	29	10′
Compound 1434	30	30	30	10′
Compound 1435	31	31	31	10′
Compound 1436	32	32	32	10′
Compound 1437	33	33	33	10′
Compound 1438	34	34	34	10′
Compound 1439	35	35	35	10′
Compound 1440	36	36	36	10′

TABLE 51

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1441	1	1	1	11′
Compound 1442	2	2	2	11′
Compound 1443	3	3	3	11′
Compound 1444	4	4	4	11′
Compound 1445	5	5	5	11′
Compound 1446	6	6	6	11′
Compound 1447	7	7	7	11′
Compound 1448	8	8	8	11′
Compound 1449	9	9	9	11′
Compound 1450	10	10	10	11′
Compound 1451	11	11	11	11′
Compound 1452	12	12	12	11′
Compound 1453	13	13	13	11′
Compound 1454	14	14	14	11′
Compound 1455	15	15	15	11′
Compound 1456	16	16	16	11′
Compound 1457	17	17	17	11′
Compound 1458	18	18	18	11′
Compound 1459	19	19	19	11′
Compound 1460	20	20	20	11′
Compound 1461	21	21	21	11′
Compound 1462	22	22	22	11′
Compound 1463	23	23	23	11′
Compound 1464	24	24	24	11′
Compound 1465	25	25	25	11′
Compound 1466	26	26	26	11′
Compound 1467	27	27	27	11′
Compound 1468	28	28	28	11′
Compound 1469	29	29	29	11′
Compound 1470	30	30	30	11′
Compound 1471	31	31	31	11′
Compound 1472	32	32	32	11′
Compound 1473	33	33	33	11′
Compound 1474	34	34	34	11′
Compound 1475	35	35	35	11′
Compound 1476	36	36	36	11′

TABLE 52

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1477	1	1	1	12′
Compound 1478	2	2	2	12′
Compound 1479	3	3	3	12′
Compound 1480	4	4	4	12′
Compound 1481	5	5	5	12′
Compound 1482	6	6	6	12′
Compound 1483	7	7	7	12′
Compound 1484	8	8	8	12′
Compound 1485	9	9	9	12′
Compound 1486	10	10	10	12′
Compound 1487	11	11	11	12′
Compound 1488	12	12	12	12′
Compound 1489	13	13	13	12′
Compound 1490	14	14	14	12′
Compound 1491	15	15	15	12′
Compound 1492	16	16	16	12′
Compound 1493	17	17	17	12′
Compound 1494	18	18	18	12′
Compound 1495	19	19	19	12′
Compound 1496	20	20	20	12′
Compound 1497	21	21	21	12′
Compound 1498	22	22	22	12′
Compound 1499	23	23	23	12′
Compound 1500	24	24	24	12′
Compound 1501	25	25	25	12′
Compound 1502	26	26	26	12′
Compound 1503	27	27	27	12′
Compound 1504	28	28	28	12′
Compound 1505	29	29	29	12′
Compound 1506	30	30	30	12′
Compound 1507	31	31	31	12′
Compound 1508	32	32	32	12′
Compound 1509	33	33	33	12′
Compound 1510	34	34	34	12′
Compound 1511	35	35	35	12′
Compound 1512	36	36	36	12′

TABLE 53

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1513	1	1	1	13′
Compound 1514	2	2	2	13′
Compound 1515	3	3	3	13′
Compound 1516	4	4	4	13′
Compound 1517	5	5	5	13′
Compound 1518	6	6	6	13′
Compound 1519	7	7	7	13′
Compound 1520	8	8	8	13′
Compound 1521	9	9	9	13′
Compound 1522	10	10	10	13′
Compound 1523	11	11	11	13′
Compound 1524	12	12	12	13′
Compound 1525	13	13	13	13′
Compound 1526	14	14	14	13′
Compound 1527	15	15	15	13′
Compound 1528	16	16	16	13′
Compound 1529	17	17	17	13′
Compound 1530	18	18	18	13′
Compound 1531	19	19	19	13′
Compound 1532	20	20	20	13′
Compound 1533	21	21	21	13′
Compound 1534	22	22	22	13′
Compound 1535	23	23	23	13′
Compound 1536	24	24	24	13′
Compound 1537	25	25	25	13′
Compound 1538	26	26	26	13′
Compound 1539	27	27	27	13′
Compound 1540	28	28	28	13′
Compound 1541	29	29	29	13′
Compound 1542	30	30	30	13′
Compound 1543	31	31	31	13′
Compound 1544	32	32	32	13′
Compound 1545	33	33	33	13′
Compound 1546	34	34	34	13′
Compound 1547	35	35	35	13′
Compound 1548	36	36	36	13′

TABLE 54

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1549	1	1	1	14′
Compound 1550	2	2	2	14′
Compound 1551	3	3	3	14′
Compound 1552	4	4	4	14′
Compound 1553	5	5	5	14′
Compound 1554	6	6	6	14′
Compound 1555	7	7	7	14′
Compound 1556	8	8	8	14′
Compound 1557	9	9	9	14′
Compound 1558	10	10	10	14′
Compound 1559	11	11	11	14′
Compound 1560	12	12	12	14′
Compound 1561	13	13	13	14′
Compound 1562	14	14	14	14′
Compound 1563	15	15	15	14′
Compound 1564	16	16	16	14′
Compound 1565	17	17	17	14′
Compound 1566	18	18	18	14′
Compound 1567	19	19	19	14′
Compound 1568	20	20	20	14′
Compound 1569	21	21	21	14′
Compound 1570	22	22	22	14′
Compound 1571	23	23	23	14′
Compound 1572	24	24	24	14′
Compound 1573	25	25	25	14′
Compound 1574	26	26	26	14′
Compound 1575	27	27	27	14′
Compound 1576	28	28	28	14′
Compound 1577	29	29	29	14′
Compound 1578	30	30	30	14′
Compound 1579	31	31	31	14′
Compound 1580	32	32	32	14′
Compound 1581	33	33	33	14′
Compound 1582	34	34	34	14′
Compound 1583	35	35	35	14′
Compound 1584	36	36	36	14′

TABLE 55

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1585	1	1	1	15′
Compound 1586	2	2	2	15′
Compound 1587	3	3	3	15′
Compound 1588	4	4	4	15′
Compound 1589	5	5	5	15′
Compound 1590	6	6	6	15′
Compound 1591	7	7	7	15′
Compound 1592	8	8	8	15′
Compound 1593	9	9	9	15′
Compound 1594	10	10	10	15′
Compound 1595	11	11	11	15′
Compound 1596	12	12	12	15′
Compound 1597	13	13	13	15′
Compound 1598	14	14	14	15′
Compound 1599	15	15	15	15′
Compound 1600	16	16	16	15′
Compound 1601	17	17	17	15′
Compound 1602	18	18	18	15′
Compound 1603	19	19	19	15′
Compound 1604	20	20	20	15′
Compound 1605	21	21	21	15′
Compound 1606	22	22	22	15′
Compound 1607	23	23	23	15′
Compound 1608	24	24	24	15′
Compound 1609	25	25	25	15′
Compound 1610	26	26	26	15′
Compound 1611	27	27	27	15′
Compound 1612	28	28	28	15′
Compound 1613	29	29	29	15′
Compound 1614	30	30	30	15′
Compound 1615	31	31	31	15′
Compound 1616	32	32	32	15′
Compound 1617	33	33	33	15′
Compound 1618	34	34	34	15′
Compound 1619	35	35	35	15′
Compound 1620	36	36	36	15′

TABLE 56

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1837	1	1	1	16′
Compound 1838	2	2	2	16′
Compound 1839	3	3	3	16′
Compound 1840	4	4	4	16′
Compound 1841	5	5	5	16′
Compound 1842	6	6	6	16′
Compound 1843	7	7	7	16′
Compound 1844	8	8	8	16′
Compound 1845	9	9	9	16′
Compound 1846	10	10	10	16′
Compound 1847	11	11	11	16′
Compound 1848	12	12	12	16′
Compound 1849	13	13	13	16′
Compound 1850	14	14	14	16′
Compound 1851	15	15	15	16′
Compound 1852	16	16	16	16′
Compound 1853	17	17	17	16′
Compound 1854	18	18	18	16′
Compound 1855	19	19	19	16′
Compound 1856	20	20	20	16′
Compound 1857	21	21	21	16′
Compound 1858	22	22	22	16′
Compound 1859	23	23	23	16′
Compound 1860	24	24	24	16′
Compound 1861	25	25	25	16′
Compound 1862	26	26	26	16′
Compound 1863	27	27	27	16′
Compound 1864	28	28	28	16′
Compound 1865	29	29	29	16′
Compound 1866	30	30	30	16′
Compound 1867	31	31	31	16′
Compound 1868	32	32	32	16′
Compound 1869	33	33	33	16′
Compound 1870	34	34	34	16′
Compound 1871	35	35	35	16′
Compound 1872	36	36	36	16′

TABLE 57

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1873	1	1	1	17′
Compound 1874	2	2	2	17′
Compound 1875	3	3	3	17′
Compound 1876	4	4	4	17′
Compound 1877	5	5	5	17′
Compound 1878	6	6	6	17′
Compound 1879	7	7	7	17′
Compound 1880	8	8	8	17′
Compound 1881	9	9	9	17′
Compound 1882	10	10	10	17′
Compound 1883	11	11	11	17′
Compound 1884	12	12	12	17′
Compound 1885	13	13	13	17′
Compound 1886	14	14	14	17′
Compound 1887	15	15	15	17′
Compound 1888	16	16	16	17′
Compound 1889	17	17	17	17′
Compound 1890	18	18	18	17′
Compound 1891	19	19	19	17′
Compound 1892	20	20	20	17′
Compound 1893	21	21	21	17′
Compound 1894	22	22	22	17′
Compound 1895	23	23	23	17′
Compound 1896	24	24	24	17′
Compound 1897	25	25	25	17′
Compound 1898	26	26	26	17′
Compound 1899	27	27	27	17′
Compound 1900	28	28	28	17′
Compound 1901	29	29	29	17′
Compound 1902	30	30	30	17′
Compound 1903	31	31	31	17′
Compound 1904	32	32	32	17′
Compound 1905	33	33	33	17′
Compound 1906	34	34	34	17′
Compound 1907	35	35	35	17′
Compound 1908	36	36	36	17′

TABLE 58

Compound No.	D 1A	D 1B	D 1C	D 2A
Compound 1909	1	1	1	18′
Compound 1910	2	2	2	18′
Compound 1911	3	3	3	18′
Compound 1912	4	4	4	18′
Compound 1913	5	5	5	18′
Compound 1914	6	6	6	18′
Compound 1915	7	7	7	18′
Compound 1916	8	8	8	18′
Compound 1917	9	9	9	18′
Compound 1918	10	10	10	18′
Compound 1919	11	11	11	18′
Compound 1920	12	12	12	18′
Compound 1921	13	13	13	18′
Compound 1922	14	14	14	18′
Compound 1923	15	15	15	18′
Compound 1924	16	16	16	18′
Compound 1925	17	17	17	18′
Compound 1926	18	18	18	18′
Compound 1927	19	19	19	18′
Compound 1928	20	20	20	18′
Compound 1929	21	21	21	18′
Compound 1930	22	22	22	18′
Compound 1931	23	23	23	18′
Compound 1932	24	24	24	18′
Compound 1933	25	25	25	18′
Compound 1934	26	26	26	18′
Compound 1935	27	27	27	18′
Compound 1936	28	28	28	18′
Compound 1937	29	29	29	18′
Compound 1938	30	30	30	18′
Compound 1939	31	31	31	18′
Compound 1940	32	32	32	18′
Compound 1941	33	33	33	18′
Compound 1942	34	34	34	18′
Compound 1943	35	35	35	18′
Compound 1944	36	36	36	18′

TABLE 61 — Evaluation

	Emitting layer		EQE
	first	second	third	drive voltage	at low current			λp
	compound	compound	compound	(relative value: %)	(relative value: %)	CIEx	CIEy	[nm]
Example 12A-1	TADF12	RD-1	CBP	98	226	0.66	0.34	620
Example 12A-2	TADF16	RD-1	CBP	97	231	0.65	0.35	619
Comparative 12B	comparative	RD-1	CBP	100	100	0.66	0.34	621
	compound 2

TABLE 62

	Emitting layer	Evaluation
	first	second	third	drive voltage			λp
	compound	compound	compound	(relative value: %)	CIEx	CIEy	[nm]
Example 13A	TADF7	RD-1	CBP	96	0.64	0.36	619
Comparative 13B	comparative	RD-1	CBP	100	0.64	0.36	619
	compound 1

TABLE 63

	Emitting layer	Evaluation
	first	second	third	drive voltage			λp
	compound	compound	compound	(relative value:%)	CIEx	CIEy	[nm]
Example 13A-1	TADF13	RD-1	CBP	93	0.64	0.36	620
Comparative 13B	comparative	RD-1	CBP	100	0.64	0.36	619
	compound 1

TABLE 64 — Evaluation

	Emitting layer		EQE
	first	second	third	drive voltage	at low current			λp
	compound	compound	compound	(relative value: %)	(relative value: %)	CIEx	CIEy	[nm]
Example 14A	TADF6	RD-1	CBP	98	116	0.65	0.35	620
Comparative 14B	comparative	RD-1	CBP	100	100	0.66	0.34	620
	compound 3

TABLE 65 — Evaluation

	Emitting layer		EQE
	first	second	third	drive voltage	at low current	at high current			λp
	compound	compound	compound	(relative value: %)	(relative value: %)	(relative value: %)	CIEx	CIEy	[nm]
Example 15A	TADF18	RD-1	CBP	95	186	250	0.66	0.34	620
Example 15A-1	TADF20	RD-1	CBP	98	252	260	0.66	0.34	620
Example 15A-2	TADF22	RD-1	CBP	97	256	288	0.66	0.34	620
Example 15A-3	TADF28	RD-1	CBP	100	215	228	0.66	0.34	620
Example 15A-4	TADF37	RD-1	CBP	98	250	270	0.66	0.34	620
Example 15A-5	TADF38	RD-1	CBP	100	213	220	0.66	0.34	620
Comparative 12B	comparative	RD-1	CBP	100	100	100	0.66	0.34	621
	compound 2

TABLE 66 — Evaluation

	Emitting layer		EQE
	first	second	third	drive voltage	at low current	at high current			λp
	compound	compound	compound	(relative value: %)	(relative value: %)	(relative value: %)	CIEx	CIEy	[nm]
Example 16A	TADF22	RD-2	CBP	96	226	194	0.67	0.33	621
Comparatiw 16B	comparative	RD-2	CBP	100	100	100	0.67	0.33	621
	compound 2
Example 16A-1	TADF22	RD-3	CBP	96	224	180	0.66	0.34	611
Comparative 16B-1	comparative	RD-3	CBP	100	100	100	0.66	0.34	611
	compound 2
Example 16A-2	TADF22	RD-4	CBP	94	356	334	0.58	0.42	597
Comparative 16B-2	comparative	RD-4	CBP	100	100	100	0.61	0.39	604
	compound 2

Claims as granted

36 claims

Classifications

7 codes

IPC · International Patent Classification

Section C — Chemistry; metallurgy

C07D209/94
C07D491/048
C07D495/04
C07D491/04
C09K11/02
C09K11/06

Section H — Electricity

H10K99/00

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Shawquia Jackson

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