Korean Patent Application No. 10-2014-0163822, filed on Nov. 21, 2014, in the Korean Intellectual Property Office, and entitled: “Amine-Based Compounds and Organic Light-Emitting Devices Comprising The Same,” is incorporated by reference herein in its entirety.

›BACKGROUND

1. Field

Embodiments relate to an amine-based compound, and an organic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs), which are self-emitting devices, have advantages such as wide viewing angles, excellent contrast, quick response, high brightness, excellent driving voltage characteristics, and can provide multicolored images.

An organic light-emitting device may have a structure in which a first electrode, a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially disposed in the stated order on a substrate. Holes injected from the first electrode move to the emission layer via the hole transport region, while electrons injected from the second electrode move to the emission layer via the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted.

›SUMMARY · 1 of 2

Embodiments are directed to an amine-based compound represented by Formula 1:

wherein, in Formula 1,

L 1 to L 3 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

a1 to a3 are each independently an integer selected from 0 to 3, wherein at least two L 1 s are the same or different when a1 is 2 or greater, at least two L 2 s are the same or different when a2 is 2 or greater, and at least two L 2 s are the same or different when a3 is 2 or greater;

Ar 1 is a group represented by Formula 2;

Ar 2 is a group represented by Formula 3A or a group represented by Formula 3B;

Ar 3 is selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group; and

c1 to c3 are each independently an integer selected from 1 to 3, wherein at least two Ar 1 s are the same or different when c1 is 2 or greater, at least two Ar 2 s are the same or different when c2 is 2 or greater, and at least two Ar 3 s are the same or different when c3 is 2 or greater, and

in Formulae 2, 3A, and 3B,

A 1 is a ring selected from benzene, naphthalene, fluorene, phenanthrene and pyrene;

R 1 is selected from a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

X 1 and X 2 are each independently O or S;

R 2 , R 3 , R 11 , R 12 , R 21 , and R 22 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 );

b2 and b21 are each independently an integer selected from 1 to 4, wherein at least two R 2 s are the same or different when b2 is 2 or greater, and at least two R 21 s are the same or different when b21 is 2 or greater;

b3 and b11 are each independently an integer selected from 1 to 3, wherein at least two R 3 s are the same or different when b3 is 2 or greater, and at least two R 11 s are the same or different when b11 is 2 or greater;

b12 is an integer selected from 1 to 6, wherein at least two R 12 s are the same or different when b12 is 2 or greater;

b22 is an integer selected from 1 to 5, wherein at least two R 22 s are the same or different when b22 is 2 or greater;

* indicates a binding site with an adjacent atom;

at least one of substituents of the substituted C 3 -C 10 cycloalkylene group, the substituted C 1 -C 10 heterocycloalkylene group, the substituted C 3 -C 10 cycloalkenylene group, the substituted C 1 -C 10 heterocycloalkenylene group, the substituted C 6 -C 60 arylene group, the substituted C 1 -C 60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group,

›SUMMARY · 2 of 2

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 60 alkoxy group, each substituted with at least one of a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 14 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 ),

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ), and

—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), and —B(Q 36 )(Q 37 ); and

Q 1 to Q 7 , Q 11 to Q 17 , Q 21 to Q 27 , and Q 31 to Q 37 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

Embodiments are also directed to an organic light-emitting device that includes a first electrode, a second electrode opposite to the first electrode, and an organic layer between the first electrode and the second electrode and including an emission layer. The organic layer includes at least one of the amine-based compounds of Formula 1.

›BRIEF DESCRIPTION OF THE DRAWINGS

Features will become apparent to those of skill in the art by describing in detail exemplary embodiments with reference to the attached drawings in which:

FIGS. 1 to 4 illustrate schematic cross-sectional views of organic light-emitting devices according to embodiments of the present disclosure.

›DETAILED DESCRIPTION · 1 of 17

Example embodiments will now be described more fully hereinafter with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey exemplary implementations to those skilled in the art.

In the drawing figures, the dimensions of layers and regions may be exaggerated for clarity of illustration. It will also be understood that when a layer or element is referred to as being “on” another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. Further, it will be understood that when a layer is referred to as being “between” two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present. Like reference numerals refer to like elements throughout.

According to an embodiment of the present disclosure, there is provided an amine-based compound represented by Formula 1:

wherein, in Formula 1,

For example, L 1 to L 3 in Formula 1 may be each independently selected from

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoimidazolylene group, a benzofuranylene group, a benzothiophenylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzooxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a thiadiazolylene group, an imidazopyridinylene group, and an imidazopyrimidinylene group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group.

›DETAILED DESCRIPTION · 2 of 17

For example, according to an embodiment, L 1 to L 3 in Formula 1 may be each independently selected from:

a phenylene group, a naphthylene group, and a fluorenyl group, and

a phenylene group, a naphthylene group, and a fluorenyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, and a naphthyl group.

In some embodiments, L 1 to L 3 in Formula 1 may be each independently a group represented by one of Formulae 4-1 to 4-33:

In Formulae 4-1 to 4-33,

Y 1 may be O, S, C(Z 3 )(Z 4 ), N(Z 5 ), or Si(Z 6 )(Z 7 );

Z 1 to Z 7 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

d1 may be an integer selected from 1 to 4;

d2 may be an integer selected from 1 to 3;

d3 may be an integer selected from 1 to 6;

d4 may be an integer selected from 1 to 8;

d5 may be 1 or 2;

d6 may be an integer selected from 1 to 5; and

* and *′ may be each a binding site with an adjacent atom.

For example, L 1 to L 3 in Formula 1 may be each independently a group represented by one of Formulae 4-1 to 4-7.

In some embodiments, L 1 to L 3 in Formula 1 may be each independently a group represented by one of Formulae 5-1 to 5-27:

In Formulae 5-1 to 5-27, * and *′ may be each a binding site with an adjacent atom.

In Formula 1, a1, a2, and a3, which indicate the numbers of L 1 s, L 2 s, and L 3 s, respectively, may be each independently an integer selected from 0 to 3. At least two L 1 s may be the same or different when a1 is 2 or greater, at least two L 2 s may be the same or different when a2 is 2 or greater, and at least two L 3 s may be the same or different when a3 is 2 or greater. When a1, a2, and a3 are 0, *-(L 1 ) a1 -*′, *-(L 2 ) a2 -*′, and *-(L 3 ) a3 -*′, respectively, are a single bond.

For example, a1, a2, and a3 in Formula 1 may be each independently 0, 1, or 2.

In some embodiments,

a1 to a3 may be all 0;

a1=1, a2=0, and a3=0;

a1=0, a2=1, and a3=0;

a1=0, a2=0, and a3=1;

a1=1, a2=1, and a3=0;

a1=1, a2=0, and a3=1;

a1=0, a2=1, and a3=1;

a1 to a3 may be all 1; or

a1=2, a2=0, and a3=0.

In Formula 1,

Ar 1 may be a group represented by Formula 2;

Ar 2 may be a group represented by Formula 3A or a group represented by Formula 3B;

Ar 3 may be selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In Formula 2, A 1 may be a ring selected from benzene, a naphthalene, fluorene, phenanthrene, and pyrene. For example, the A 1 ring in Formula 2 may be benzene or naphthalene.

In Formula 2, R 1 may be selected from a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, R 1 in Formula 2 and Ar 3 in Formula 1 may be each independently selected from:

›DETAILED DESCRIPTION · 3 of 17

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and —Si(Q 33 )(Q 34 )(Q 35 ),

wherein Q 33 to Q 35 may be each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group.

For example, R 1 in Formula 1 and Ar 3 in Formula 1 may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and —Si(Q 33 )(Q 34 )(Q 35 ),

›DETAILED DESCRIPTION · 4 of 17

In some embodiments, R 1 in Formula 2 may be each independently selected from:

a phenyl group, a naphthyl group, and a fluorenyl group, and

a phenyl group, a naphthyl group, and a fluorenyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, and a naphthyl group.

In some embodiments. Ar 3 in Formula 1 may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, and a naphthyl group.

In some embodiments, R 1 in Formula 2 and Ar 3 in Formula 1 may be each independently selected from groups represented by Formulae 6-1 to 6-17:

In Formulae 6-1 to 6-17,

Y 31 may be O, S, C(Z 33 )(Z 34 ), or N(Z 35 );

Z 31 to Z 35 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and —Si(Q 33 )(Q 34 )(Q 35 ), wherein Q 33 to Q 35 may be each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

e1 may be an integer of 1 to 5;

e2 may be an integer of 1 to 7;

e3 may be an integer of 1 to 3;

e4 may be an integer of 1 to 4;

e5 may be an integer of 1 or 2; and

* may be a binding site with an adjacent atom.

For example, R 1 in Formula 2 may be a group represented by one of Formulae 6-1 to 6-5 and Formulae 6-14 to 6-17.

In some embodiments, R 1 in Formula 2 and Ar 3 in Formula 1 may be each independently selected from groups represented by Formulae 7-1 to 7-33:

In Formulae 7-1 to 7-33, * may be a binding site with an adjacent atom.

In Formulae 3A and 3B, X 1 and X 2 may be each independently O or S.

In some embodiments, X 1 and X 2 in Formulae 3A and 3B may be O.

In Formulae 2, 3A, and 3B, R 2 , R 3 , R 11 , R 12 , R 21 , and R 22 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ).

In some embodiments, in Formulae 2, 3A, and 3B, R 2 , R 3 , R 11 , R 12 , R 21 , and R 22 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, and —Si(Q 3 )(Q 4 )(Q 5 ), wherein Q 3 to Q 5 may be each independently selected from a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, and a naphthyl group.

›DETAILED DESCRIPTION · 5 of 17

In some embodiments, in Formulae 2, 3A, and 3B, R 2 , R 3 , R 11 , R 12 , R 21 , and R 22 may be all hydrogens.

In Formulae 2 and 3B, b2 and b21 may be are each independently an integer selected from 1 to 4, wherein at least two R 2 s may be the same or different when b2 is 2 or greater, and at least two R 21 s may be the same or different when b21 is 2 or greater.

In Formulae 2 and 3A, b3 and b11 may be each independently an integer selected from 1 to 3, wherein at least two R 3 s may be the same or different when b3 is 2 or greater, and at least two R 11 s may be the same or different when b11 is 2 or greater.

In Formula 3A, b12 may be an integer selected from 1 to 6, wherein at least two R 12 s may be the same or different when b12 is 2 or greater.

In Formula 3B, b22 may be an integer selected from 1 to 5, wherein at least two R 22 s may be the same or different when b22 is 2 or greater.

For example, in Formulae 2, 3A, and 3B, b2, b3, b11, b12, b21, and b22 may be each independently 1 or 2.

In Formula 1, c1 to c3 may be each independently an integer selected from 1 to 3, wherein at least two Ar 1 s may be the same or different when c1 is 2 or greater, at least two Ar 2 s may be the same or different when c2 is 2 or greater, and at least two Ar 3 s may be the same or different when c3 is 2 or greater. For example, in Formula 1, c1 and c2 may be 1, and c3 may be 1, 2, or 3.

In some embodiments, in according to an embodiment, Ar 1 in Formula 1 may be a group represented by one of Formulae 2-1 to 2-6:

In Formulae 2-1 to 2-6, R 1 to R 3 , b2, b3, and * may have the same definitions as described above.

For example, in Formulae 2-1 to 2-6,

R 1 may be selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, and —Si(Q 33 )(Q 34 )(Q 35 ), wherein Q 33 to Q 35 are each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group;

R 2 and R 3 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;

b2 and b3 may be each independently 1 or 2; and

* may be a binding site with an adjacent atom.

In some embodiments, Ar 1 in Formula 1 may be selected from groups represented by Formula 8-1 to 8-21:

In Formulae 8-1 to 8-21, * may be a binding site with an adjacent atom.

In some embodiments, Ar 2 in Formula 1 may be a group represented by one of Formulas 3A-1, 3B-1, 3A-2, and 3B-2:

In Formula 3A-1, 3B-1, 3A-2, and 3B-2, R 11 , R 12 , R 21 , R 22 , b11, b12, b21, b22 and * may have the same definitions as described above.

For example, in Formulae 3A-1, 3B-1, 3A-2, and 3B-2,

R 11 , R 12 , R 21 , and R 22 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;

b21 and b22 may be each independently 1 or 2; and

* may be a binding site with an adjacent atom.

In some embodiments, Ar 2 in Formula 1 may be selected from a group represented by Formula 9-1 and a group represented by Formula 9-2:

In Formulae 9-1 and 9-2, * may be a binding site with an adjacent atom.

In some embodiments, in the amine-based compound of Formula 1,

L 1 to L 3 may be each independently a group represented by one of Formulae 5-1 to 5-27;

a1 to a3 may be each independently 0, 1, or 2;

Ar 1 may be a group represented by one of Formulae 2-1 to 2-6;

Ar 2 may be a group represented by one of Formulae 3A-1, 3B-1, 3A-2, and 3B-2; and

Ar 3 may be selected from:

›DETAILED DESCRIPTION · 6 of 17

For example, the amine-based compound of Formula 1 may be one of Compounds 1 to 110:

The compound represented by Formula 1 may be an amine-based compound in which Ar 1 is a group represented by Formula 2 and Ar 2 is a group represented by Formula 3A or 3B.

Ar 2 in Formula 1 may effectively provide excess electrons from non-paired electron pairs. Accordingly, the amine-based compound of Formula 1 may have a molecular structure with abundant π-electrons. The abundance of π-electrons may increase an electron transition probability, and consequently, the amine-based compound of Formula 1 may provide an improved emission efficiency.

Due to the inclusion of Ar 1 (a carbazole-based substituent represented by Formula 2), the amine-based compound of Formula 1 may have improved hole transport capability.

The amine-based compound of Formula 1 may be synthesized using suitable organic synthesis methods, which may be understood based on the following examples that will be described below.

At least one amine-based compounds represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device. In other implementations, the amine-based compound of Formula 1 may be used as a material for capping layers disposed outwards of a pair of electrodes of an organic light-emitting device. For example, the amine-based compound of Formula 1 may be included in a hole transport region, for example, in a hole transport layer. In some embodiments, the amine-based compound of Formula 1 may be included in an emission layer of the organic light-emitting device.

According to another aspect of the present disclosure, an organic light-emitting device may include a first electrode, a second electrode disposed opposite to the first electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer. The organic layer includes at least one of the amine-based compounds of Formula 1.

As used herein, the expression that “(for example, an organic layer may include) at least one of the amine-based compounds of Formula 1” indicates that “(the organic layer may include) one of the amine-based compounds of Formula 1 or at least two different types of the amine-based compounds of Formula 1”.

For example, the organic layer may include only Compound 1 as the at least one of amine-based compounds of Formula 1. For example, Compound 1 may be in an hole transport layer of the organic light-emitting device. In some embodiments, the organic layer may include Compounds 1 and 2 as the at least one of amine-based compounds of Formula 1. For example, Compounds 1 and 2 may be in the same layer (for example, both in the hole transport layer) or in different layers (for example, Compound 1 may be in the hole transport layer, and Compound 2 may be in the emission layer).

In some embodiments, the organic layer may include i) a hole transport region disposed between the first electrode (anode) and the emission layer and including at least one of a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer, and ii) an electron transport region disposed between the emission layer and the second electrode (cathode) and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. At least one of the hole transport region and the emission layer may include the at least one of the amine-based compounds of Formula 1. For example, the hole transport region may include a hole transport layer, and the hole transport layer may include the at least one of the amine-based compounds of Formula 1.

In some embodiments, the hole transport region may include at least one of a hole injection layer and a hole transport layer, and the at least one of a hole injection layer and a hole transport layer may include the at least one of the amine-based compounds of Formula 1.

In some embodiments, the organic light-emitting device may further include at least one of a first capping layer and a second capping layer, the first capping layer being disposed on an optical path along which light generated in the emission layer passes outwardly through the first electrode, and the second capping layer being disposed on an optical path along which the light generated in the emission layer passes outwardly through the second electrode. At least one of the first and second capping layers may include at least one of the amine-based compounds of Formula 1.

›DETAILED DESCRIPTION · 7 of 17

For example, the organic light-emitting device may have i) a stack structure in which the first electrode, the organic layer, the second electrode, and the second capping layer are sequentially stacked upon one another in the stated order, ii) a stack structure in which the first capping layer, the first electrode, the organic layer, and the second electrode are sequentially stacked upon one another in the stated order, or iii) a stack structure in which the first capping layer, the first electrode, the organic layer, the second electrode, and the second capping layer are sequentially stacked upon one another in the stated order. At least one of the first capping layer and the second capping layer may include the amine-based compound of Formula 1.

As used herein, the term “organic layer” refers to a single layer and/or a plurality of layers disposed between the first and second electrodes of the organic light-emitting device. The “organic layer” may also include materials other than an organic material.

Hereinafter, a structure of an organic light-emitting device according to an embodiment of the present disclosure and a method of manufacturing the same will now be described with reference to FIG. 1 .

FIG. 1 illustrates a schematic sectional view of an organic light-emitting device 10 according to an embodiment of the present disclosure. Referring to FIG. 1 , the organic light-emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .

A substrate may be disposed under the first electrode 110 or on the second electrode 190 in FIG. 1 . The substrate may be a substrate with good mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. For example, the substrate may be a glass or transparent plastic substrate.

The first electrode 110 may be formed by depositing or sputtering a first electrode-forming material on the substrate. When the first electrode 110 is an anode, a material having a high work function may be used as the first electrode-forming material to facilitate hole injection. The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. Transparent and conductive materials such as ITO, IZO, SnO 2 , and ZnO may be used to form the first electrode. The first electrode 110 as a semi-transmissive electrode or a reflective electrode may be formed of at least one material selected from magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag).

The first electrode 110 may have a single-layer structure or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.

The organic layer 150 may be disposed on the first electrode 110 . The organic layer 150 may include an emission layer (EML).

The organic layer 150 may further include a hole transport region disposed between the first electrode and the EML, and an electron transport region between the EML and the second electrode.

For example, the hole transport region may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer, and an electron blocking layer (EBL). For example, the electron transport layer may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL). The hole transport region may have a single-layered structure including a single material, a single-layered structure including a plurality of materials, or a multi-layered structure including a plurality of layers including different materials.

In some embodiments, the hole transport region may have a single-layered structure including a plurality of materials, or a multi-layered structure of HIL/HTL, HIL/HTL/buffer layer. HIL/buffer layer, HTL/buffer layer, or HIL/HTL/EBL, wherein these layers forming a multi-layered structure are sequentially disposed on the first electrode 110 in the order stated above.

When the hole transport region includes a HIL, the HIL may be formed on the first electrode 110 by using any of a suitable method, for example, by using vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging (LITI), or the like.

When the HIL is formed using vacuum deposition, the deposition conditions may vary depending on the material that is used to form the HIL and the structure of the HIL. For example, the deposition conditions may be selected from the following conditions: a deposition temperature of about 100° C. to about 500° C., a degree of vacuum of about 10 −8 to about 10 −3 torr, and a deposition rate of about 0.01 to 100 Å/sec.

When the HIL is formed using spin coating, the coating conditions may vary depending on the material that is used to form the HIL and the structure of the HIL. For example, the coating conditions may be selected from the following conditions: a coating rate of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 800° C. to about 200° C.

When the hole transport region includes a HTL, the HTL may be formed on the first electrode 110 or the I-IL by using a suitable method, for example, by using vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging (LITI), or the like. When the HTL is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to the above-described deposition and coating conditions for forming the HIL.

The hole transport region may include the amine-based compound of Formula 1. For example, the hole transport region may include a hole transport layer, and the hole transport layer may include the amine-based compound of Formula 1.

In some embodiments, the hole transport region may include, in addition to at least one amine-based compound of Formula 1, at least one of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)(PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, and a compound represented by Formula 202.

›DETAILED DESCRIPTION · 8 of 17

In Formulae 201 and 202,

L 201 to L 205 may be each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

xa1 to xa4 may be each independently selected from 0, 1, 2, and 3;

xa5 may be selected from 1, 2, 3, 4, and 5; and

R 201 to R 205 may be defined as described above herein in conjunction with R 3 .

The compound of Formula 201 may be a compound represented by Formula 201A:

For example, the compound of Formula 201 may be a compound represented by Formula 201A-1:

The compound of Formula 202 may be a compound represented by Formula 202A:

In Formulae 201A, 201A-1, and 202A,

L 201 to L 203 , xa1 to xa3, xa5, and R 202 to R 204 may be the same as those described above herein.

R 211 and R 212 may be defined as described above herein in conjunction with R 203 .

R 213 to R 216 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulae 201A, 201A-1, and 202A,

L 201 to L 203 may be each independently selected from:

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

xa1 to xa3 may be each independently 0 or 1;

R 203 , R 204 , R 205 , R 211 , and R 212 may be each independently selected from

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

R 213 and R 214 may be each independently selected from:

a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group,

a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group,

›DETAILED DESCRIPTION · 9 of 17

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

R 215 and R 216 may be each independently selected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

xa5 may be 1 or 2.

In Formulae 201A and 201A-1, R 213 and R 214 may be linked to each other to form a saturated or unsaturated ring.

The compound of Formula 201 and the compound of Formula 202 may each independently be selected from Compounds HT1 to HT20, as examples.

A thickness of the hole transport region may be from about 100 Å to about 10,000 Å, and in some embodiments, from about 100 Å to about 1,000 Å. When the hole transport region includes a HIL and a HTL, a thickness of the HIL may be from about 100 Å to about 10,000 Å, and in some embodiments, from about 100 Å to about 1,000 Å, and a thickness of the HTL may be from about 50 Å to about 2,000 Å, and in some embodiments, from about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the HIL, and the HTL are within these ranges, satisfactory hole transport characteristics may be obtained without a substantial increase in driving voltage.

The hole transport region may further include a charge-generating material to improve conductivity, in addition to the materials as described above. The charge-generating material may be homogeneously or inhomogeneously dispersed in the hole transport region.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of quinone derivatives, metal oxides, and cyano group-containing compounds. Examples of the p-dopant include quinone derivatives such as tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), or the like; metal oxides such as tungsten oxide, molybdenum oxide, or the like; and Compound HT-D1.

›DETAILED DESCRIPTION · 10 of 17

The hole transport region may further include at least one of a buffer layer and an EBL, in addition to the HIL and HTL described above. The buffer layer may compensate for an optical resonance distance of light according to a wavelength of the light emitted from the EML, and thus may improve light-emission efficiency. A material in the buffer layer may be a suitable material for use in the hole transport region. The EBL may block migration of electrons from the electron transport region into EML.

The EML may be formed on the first electrode 110 or the hole transport region by using a suitable method, for example, by using vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging (LITI), or the like. When the EML is formed using vacuum deposition or spin coating, the deposition and coating conditions for forming the EML may be similar to the above-described deposition and coating conditions for forming the HIL.

When the organic light-emitting device 10 is a full color organic light-emitting device, the EML may be patterned into a red emission layer, a green emission layer, and a blue emission layer to correspond to individual subpixels, respectively. In some embodiments, the EML may have a structure in which a red emission layer, a green emission layer and a blue emission layer are stacked upon one another, or a structure including a mixture of a red light-emitting material, a green light-emitting material, and a blue light-emitting material without separation of layers for the different color emission, and thus may emit white light.

The EML may include a host and a dopant.

In some embodiments, the host may include a compound represented by Formula 301.

Ar 301 -[(L 301 ) xb1 -R 301 ] xb2 Formula 301

In Formula 301,

Ar 301 may be selected from:

a naphthalene group, a heptalene group, a fluorene group, a spiro-fluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 301 )(Q 302 )(Q 303 ), wherein Q 301 to Q 303 may be each independently selected from a hydrogen, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group:

L 301 may be defined as described above herein in conjunction with L 1 ,

R 301 may be selected from:

a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, and a triazinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;

›DETAILED DESCRIPTION · 11 of 17

xb1 may be selected from 0, 1, 2, and 3;

xb2 may be selected from 1, 2, 3, and 4.

For example, in Formula 301, L 301 may be selected from

R 301 may be selected from

a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group,

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group.

For example, the host may include a compound represented by Formula 301A:

In Formula 301A, L 301 , xb1, R 301 and xb2 may be the same as those defined herein.

The compound of Formula 301 may include at least one of Compounds H1 to H42.

In some embodiments, the host may include at least one of Compounds H43 to H49:

The dopant for the EML may include a phosphorescent dopant or a fluorescent dopant.

The phosphorescent dopant may include an organic metal complex represented by Formula 401:

M may be selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), halfnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),

X 401 to X 404 may be each independently a nitrogen or a carbon,

the A 401 and A 402 rings may be each independently selected from a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted spiro-fluorene, a substituted or unsubstituted indene, a substituted or unsubstituted pyrrole, a substituted or unsubstituted thiophene, a substituted or unsubstituted furan, a substituted or unsubstituted imidazole, a substituted or unsubstituted pyrazole, a substituted or unsubstituted thiazole, a substituted or unsubstituted isothiazole, a substituted or unsubstituted oxazole, a substituted or unsubstituted isoxazole, a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrazine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted pyridazine, a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted benzoquinoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted quinazoline, a substituted or unsubstituted carbazole, a substituted or unsubstituted benzoimidazole, a substituted or unsubstituted benzofuran, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted isobenzothiophene, a substituted or unsubstituted benzoxazole, a substituted or unsubstituted isobenzoxazole, a substituted or unsubstituted triazole, a substituted or unsubstituted oxadiazole, a substituted or unsubstituted triazine, a substituted or unsubstituted dibenzofuran, and a substituted or unsubstituted dibenzothiophene,

at least one of substituents of the substituted benzene, the substituted naphthalene, the substituted fluorene, the substituted spiro-fluorene, the substituted indene, the substituted pyrrole, the substituted thiophene, the substituted furan, the substituted imidazole, the substituted pyrazole, the substituted thiazole, the substituted isothiazole, the substituted oxazole, the substituted isoxazole, the substituted pyridine, the substituted pyrazine, the substituted pyrimidine, the substituted pyridazine, the substituted quinoline, the substituted isoquinoline, the substituted benzoquinoline, the substituted quinoxaline, the substituted quinazoline, the substituted carbazole, the substituted benzoimidazole, the substituted benzofuran, the substituted benzothiophene, the substituted isobenzothiophene, the substituted benzoxazole, the substituted isobenzoxazole, the substituted triazole, the substituted oxadiazole, the substituted triazine, the substituted dibenzofuran, and the substituted dibenzothiophene may be selected from:

›DETAILED DESCRIPTION · 12 of 17

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 401 )(Q 402 ), —Si(Q 403 )(Q 404 )(Q 405 ), and —B(Q 406 )(Q 407 ),

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 411 )(Q 412 ), —Si(Q 413 )(Q 414 )(Q 415 ) and —B(Q 416 )(Q 417 ), and

—N(Q 421 )(Q 422 ), —Si(Q 423 )(Q 424 )(Q 425 ), and —B(Q 426 )(Q 427 ),

L 401 may be an organic ligand,

xc1 may be 1, 2, or 3; and

xc2 may be 0, 1, 2, or 3.

For example, L 401 may be a monovalent, divalent, or trivalent organic ligand. For example, L 401 may be selected from a halogen ligand (for example, Cl or F), a diketone ligand (for example, acetylacetonate, 1,3-diphenyl-1,3-propanedionate, 2,2,6,6-tetramethyl-3,5-heptanedionate, or hexafluoroacetonate), a carboxylic acid ligand (for example, picolinate, dimethyl-3-pyrazole carboxylate, or benzoate), a carbon monoxide ligand, an isonitrile ligand, a cyano ligand, and a phosphorous ligand (for example, phosphine or phosphite).

For example, Q 401 to Q 407 , Q 411 to Q 417 , and Q 421 to Q 427 may be each independently selected from a hydrogen, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group.

When A 401 in Formula 401 has at least two substituents, the at least two substituents of A 401 may be linked to each other to form a saturated or unsaturated ring.

When A 402 in Formula 401 has at least two substituents, the at least two substituents of A 402 may be linked to each other to form a saturated or unsaturated ring.

When xc1 in Formula 401 is 2 or greater, the plurality of ligands in Formula 401, represented by

may be identical to or different from each other. When xc1 in Formula 401 is 2 or greater, A 401 and A 402 may be linked to A 401 and A 402 of another adjacent ligand directly or via a linker (for example, a C 1 -C 5 alkylene group, —N(R′)— (where R′ is a C 1 -C 10 alkyl group or a C 6 -C 20 aryl group), or —C(═O)—).

For example, the fluorescent dopant may include a compound represented by Formula 501:

In Formula 501,

Ar 501 may be selected from:

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, a benzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, an anthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, naphthacene, a picene, a perylene, a pentaphene, and an indenoanthracene, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 501 )(Q 502 )(Q 503 ), wherein Q 501 to Q 503 may be each independently selected from a hydrogen, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group;

›DETAILED DESCRIPTION · 13 of 17

L 501 to L 503 may be defined as described above herein in conjunction with L 1 ;

R 501 and R 502 may be each independently selected from

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

xd1 to xd3 may be each independently selected from 0, 1, 2, and 3; and

xb4 may be selected from 1, 2, 3, and 4.

For example, the fluorescent host may include at least one of Compounds FD1 to FD9:

An amount of the dopant in the EML may be from about 0.01 parts to about 15 parts by weight based on 100 parts by weight of the host.

A thickness of the EML may be about 100 Å to about 1,000 Å, and in some embodiments, may be from about 200 Å to about 600 Å. When the thickness of the EML is within these ranges, the EML may have good light emitting ability without a substantial increase in driving voltage.

Next, the electron transport region may be formed on the EML.

The electron transport region may include at least one of a HBL, an ETL, and an EIL. In some embodiments, the electron transport region may have a structure including an ETL/EIL or a HBL/ETL/EIL, wherein the layers forming a structure of the electron transport region may be sequentially stacked on the EML in the order stated above.

In some embodiments, in the organic light-emitting device 10 of FIG. 1 , the organic layer 150 may include an electron transport region between the EML and the second electrode 190 .

When the electron transport region includes a HBL, the HBL may be formed on the EML by using a suitable method, for example, by using vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging (LITI), or the like. When the HBL is formed using vacuum deposition or spin coating, the deposition and coating conditions for forming the HBL may be similar to the above-described deposition and coating conditions for forming the HIL.

For example, the HBL may include at least one of BCP and Bphen.

A thickness of the HBL may be from about 20 Å to about 1,000 Å, and in some embodiments, from about 30 Å to about 300 Å. When the thickness of the HBL is within these ranges, the HBL may have improved hole blocking ability without a substantial increase in driving voltage.

The electron transport region may include an ETL. The ETL may be formed on the EML or the HBL by using any of a variety of methods, for example, by using vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging (LITI), or the like. When the ETL is formed using vacuum deposition or spin coating, the deposition and coating conditions for forming the ETL may be similar to the above-described deposition and coating conditions for forming the HIL.

In some embodiments, the ETL may include at least one of a compound represented by Formula 601 and a compound represented by Formula 602:

Ar 601 -[(L 601 ) xc1 -E 601 ] xc2 Formula 601

In Formula 601,

Ar 601 may be selected from

a naphthalene, a heptalene, a fluorene, a spiro-fluorene, a benzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, an anthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, naphthacene, a picene, a perylene, a pentaphene, and an indenoanthracene, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 301 )(Q 302 )(Q 303 ), wherein Q 301 to Q 303 may be each independently selected from a hydrogen, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group:

›DETAILED DESCRIPTION · 14 of 17

L 601 may be defined as described above herein in conjunction with L 1 ;

E 601 may be selected from:

a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;

xe1 may be selected from 0, 1, 2, and 3; and

xe2 may be selected from 1, 2, 3, and 4.

In Formula 602,

X 611 may be N or C-(L 611 ) xe611 -R 611 , X 612 may be N or C-(L 612 ) xe612 -R 612 , X 613 may be N or C-(L 613 ) xe613 -R 613 , at least one of X 611 to X 613 may be N;

L 611 to L 616 may be defined as described above in conjunction with L 1 ;

R 611 to R 616 may be each independently selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an azulenyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

›DETAILED DESCRIPTION · 15 of 17

xe611 to xe616 may be each independently selected from, 0, 1, 2, and 3.

The compound of Formula 601 and the compound of Formula 602 may each independently selected from Compounds ET1 to ET15:

In some embodiments, the ETL may include at least one of BCP, Bphen, Alq 3 , Balq, TAZ, and NTAZ.

A thickness of the ETL may be from about 100 Å to about 1,000 Å, and in some embodiments, from about 150 Å to about 500 Å. When the thickness of the ETL is within these ranges, the ETL may have satisfactory electron transporting ability without a substantial increase in driving voltage.

In some embodiments the ETL may further include a metal-containing material, in addition to the above-described materials.

The metal-containing material may include a lithium (Li) complex. Non-limiting examples of the Li complex are compound ET-D1 (lithium quinolate (LiQ)), and compound ET-D2

The electron transport region may include an EIL that may facilitate injection of electrons from the second electrode 190 .

The EIL may be formed on the ETL by a suitable method, for example, by using vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging (LITI), or the like. When the EIL is formed using vacuum deposition or spin coating, the deposition and coating conditions for forming the EIL may be similar to the above-described deposition and coating conditions for forming the HIL.

The EIL may include at least one selected from LiF, NaCl, CsF, Li 2 O, BaO, and LiQ.

A thickness of the EIL may be from about 1 Å to about 100 Å, and in some embodiments, from about 3 Å to about 90 Å. When the thickness of the EIL is within these ranges, the EIL may have satisfactory electron injection ability without a substantial increase in driving voltage.

The second electrode 190 may be disposed on the organic layer 150 , as described above. The second electrode 190 may be a cathode as an electron injecting electrode. A material for forming the second electrode 190 may be a metal, an alloy, an electrically conductive compound, which have a low-work function, or a mixture thereof. Examples of materials for forming the second electrode 190 include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag). In some embodiments, a material for forming the second electrode 190 may be ITO or IZO. The second electrode 190 may be a semi-transmissive electrode or a transmissive electrode.

FIGS. 2 to 4 illustrate schematic sectional views of organic light-emitting devices 20 , 30 , and 40 , respectively, according to embodiments of the present disclosure. The organic light-emitting device 20 of FIG. 2 may have a stack structure in which a first capping layer 210 , a first electrode 110 , an organic layer 150 , and a second electrode 190 are sequentially stacked upon one another in the stated order. The organic light-emitting device 30 of FIG. 3 may have a stack structure in which a first electrode 110 , an organic layer 150 , a second electrode 190 , and a second capping layer 220 are sequentially stacked upon one another in the stated order. The organic light-emitting device 40 of FIG. 4 may have a stack structure in which a first capping layer 210 , a first electrode 110 , an organic layer 150 , a second electrode 190 , and a second capping layer 220 are sequentially stacked upon one another in the stated order.

In FIGS. 2 to 4 , the first electrode 110 , the organic layer 150 , and the second electrode 190 may be the same as those described above with reference to FIG. 1 .

In the organic light-emitting devices 20 and 40 , light generated in the emission layer of the organic layer 150 may be extracted from the organic light-emitting device through the first electrode 110 , which may be a semi-transmissive or transmissive electrode, and then through the first capping layer 210 . In the organic light-emitting devices 30 and 40 , light generated in the emission layer of the organic layer 150 may be extracted from the organic light-emitting device through the second electrode 190 , which may be a semi-transmissive or transmissive electrode, and then through the second capping layer 220 .

The first capping layer 210 and the second capping layer 220 may improve external emission efficiency based on the principle of constructive interference.

The first capping layer 210 of FIG. 2 and the second capping layer 220 of FIG. 3 may include at least one amine-based compound of Formula 1.

In the organic light-emitting device 40 of FIG. 4 , at least one of the first capping layer 210 and the second capping layer 220 may include at least one amine-based compound of Formula 1.

In some embodiments, in the organic light-emitting devices 20 , 30 , and 40 of FIGS. 2 to 4 , the organic layer 150 may not include the amine-based compound of Formula 1.

Although the organic light-emitting devices of FIGS. 1 to 4 are described above, other configurations of organic light-emitting devices may include the amine based compound of Formula 1.

As used herein, the term “C 1 -C 60 alkyl group” refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Examples of the C 1 -C 60 alkyl group include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. The term “C 1 -C 60 alkylene group” refers to a divalent group having the same structure as the C 1 -C 60 alkyl.

As used herein, the term “C 1 -C 60 alkoxy group” refers to a monovalent group represented by —OA 101 (where A 101 is a C 1 -C 60 alkyl group, as described above. Examples of the C 1 -C 60 alkoxy group include a methoxy group, an ethoxy group, and an isopropyloxy group.

As used herein, the term “C 2 -C 60 alkenyl group” refers to a hydrocarbon group including at least one carbon double bond in the middle or terminal of the C 2 -C 60 alkyl group. Examples of the C 2 -C 60 alkenyl group include an ethenyl group, a propenyl group, and a butenyl group. The term “C 2 -C 60 alkylene group” refers to a divalent group having the same structure as the C 2 -C 60 alkenyl group.

›DETAILED DESCRIPTION · 16 of 17

As used herein, the term “C 2 -C 60 alkynyl group” refers to a hydrocarbon group including at least one carbon triple bond in the middle or terminal of the C 2 -C 60 alkyl group. Examples of the C 2 -C 60 alkynyl group include an ethynyl group, and a propynyl group. The term “C 2 -C 60 alkynylene group” used herein refers to a divalent group having the same structure as the C 2 -C 60 alkynyl group.

As used herein, the term “C 3 -C 10 cycloalkyl group” refers to a monovalent, monocyclic hydrocarbon group having 3 to 10 carbon atoms. Examples of the C 3 -C 10 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C 3 -C 10 cycloalkylene group” refers to a divalent group having the same structure as the C 3 -C 10 cycloalkyl group.

As used herein, the term “C 1 -C 10 heterocycloalkyl group” refers to a monovalent monocyclic group having 1 to 10 carbon atoms in which at least one hetero atom selected from N, O, Si, P, and S is included as a ring-forming atom. Examples of the C 1 -C 10 heterocycloalkyl group include a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C 1 -C 10 heterocycloalkylene group” refers to a divalent group having the same structure as the C 1 -C 10 heterocycloalkyl group.

As used herein, the term “C 3 -C 10 cycloalkenyl group” refers to a monovalent monocyclic group having 3 to 10 carbon atoms that includes at least one double bond in the ring but does not have aromaticity. Examples of the C 3 -C 10 cycloalkenyl group include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C 3 -C 10 cycloalkenylene group” refers to a divalent group having the same structure as the C 3 -C 10 cycloalkenyl group.

As used herein, the term “C 1 -C 10 heterocycloalkenyl group” used herein refers to a monovalent monocyclic group having 1 to 10 carbon atoms that includes at least one double bond in the ring and in which at least one hetero atom selected from N, O, Si, P, and S is included as a ring-forming atom. Examples of the C 1 -C 10 heterocycloalkenyl group include a 2,3-hydrofuranyl group, and a 2,3-hydrothiophenyl group. The term “C 1 -C 10 heterocycloalkenylene group” used herein refers to a divalent group having the same structure as the C 1 -C 10 heterocycloalkenyl group.

As used herein, the term “C 6 -C 60 aryl group” refers to a monovalent, aromatic carbocyclic aromatic group having 6 to 60 carbon atoms. The term “C 6 -C 60 arylene group” refers to a divalent, aromatic carbocyclic group having 6 to 60 carbon atoms. Examples of the C 6 -C 60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C 6 -C 60 aryl group, and the C 6 -C 60 arylene group include at least two rings, the rings may be fused to each other.

As used herein, the term “C 1 -C 60 heteroaryl group” refers to a monovalent, aromatic carbocyclic aromatic group in which at least one hetero atom selected from N, O, Si, P, and S is included as a ring-forming atom, and 1 to 60 carbon atoms. The term “C 1 -C 60 heteroarylene group” refers to a divalent, aromatic carbocyclic group in which at least one hetero atom selected from N, O, Si, P, and S is included as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C 1 -C 60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C 1 -C 60 heteroaryl group and the C 1 -C 60 heteroarylene group include at least two rings, the rings may be fused to each other.

As used herein, the term “C 6 -C 60 aryloxy group” indicates —OA 102 (where A 102 is a C 6 -C 60 aryl group, as described above), and a C 6 -C 60 arylthio group indicates —SA 103 (where A 103 is a C 6 -C 60 aryl group, as described above).

As used herein, the term “monovalent non-aromatic condensed polycyclic group” (including, for example, 8 to 60 carbon atoms) refers to a monovalent group that includes at least two rings condensed to each other and includes only carbon atoms as ring-forming atoms and that represents non-aromaticity as a whole. An example of the monovalent non-aromatic condensed polycyclic group is a fluorenyl group. As used herein, the term “divalent non-aromatic condensed polycyclic group” refers to a divalent group with the same structure as the monovalent non-aromatic condensed polycyclic group.

As used herein, the term “monovalent non-aromatic condensed heteropolycyclic group” (including, for example, 1 to 60 carbon atoms) refers to a monovalent group that includes at least two rings condensed to each other and includes carbon and hetero atoms selected from N, O, Si, P and S as ring-forming atoms and that represents non-aromaticity as a whole. An example of the monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. As used herein, the term “divalent non-aromatic condensed heteropolycyclic group” refers to a divalent group with the same structure as the monovalent non-aromatic condensed polycyclic group.

As used herein, at least one of substituents of the substituted C 3 -C 10 cycloalkylene group, the substituted C 1 -C 10 heterocycloalkylene group, the substituted C 3 -C 10 cycloalkenylene group, the substituted C 1 -C 10 heterocycloalkenylene group, the substituted C 6 -C 60 arylene group, the substituted C 1 -C 60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

›DETAILED DESCRIPTION · 17 of 17

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one of a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 ),

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 10 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ) and —B(Q 26 )(Q 27 ), and

—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), and —B(Q 36 )(Q 37 ),

wherein Q 1 to Q 7 , Q 11 to Q 17 , Q 21 to Q 27 and Q 31 to Q 37 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

The acronym “Ph” used herein refers to phenyl, the acronym “Me” used herein refers to methyl, the acronym “Et” used herein refers to ethyl, and the acronym “ter-Bu” or “Bu t ” used herein refers to tert-butyl.

The following Examples and Comparative Examples are provided in order to highlight characteristics of one or more embodiments, but it will be understood that the Examples and Comparative Examples are not to be construed as limiting the scope of the embodiments, nor are the Comparative Examples to be construed as being outside the scope of the embodiments. Further, it will be understood that the embodiments are not limited to the particular details described in the Examples and Comparative Examples. In the following synthesis examples, the expression that “‘B’ instead of ‘A’ was used” indicates that the amounts of ‘B’ and ‘A’ were the same in equivalent amounts.

›EXAMPLE · 1 of 5

Synthesis Example 1: Synthesis of Compound 3

Synthesis of Intermediate 1-1

3.13 g (10 mmol) of 2-bromo-1-iodo-4-methoxybenzene, 1.58 g (11 mmol) of 1-naphthol, 0.112 g (0.5 mmol) of palladium acetate, 0.651 g (2.0 mmol) of triphenylphosphine, and 13 g (40 mmol) of cesium carbonate were dissolved in 60 mL of dimethylformamide (DMF), and stirred at about 140° C. for about 24 hours. The resulting reaction solution was cooled down to room temperature, followed by adding 60 mL of water and extraction three times with 60 mL of ethyl ether. An organic phase was collected using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 1.64 g of Intermediate I-1 (Yield: 66%). This compound was identified using mass spectroscopy/fast atom bombardment (MS/FAB).

C 17 H 12 O 2 : calc. 248.08, found 248.10.

Synthesis of Intermediate 1-2

1.64 g (6.6 mmol) of Intermediate I-1 was dissolved in 60 mL of methyl chloride (MC), and 0.93 mL (9.9 mmol) of BBr 3 was slowly dropwise added thereto at about −78° C. The temperature of the resulting reaction solution was increased to room temperature and stirred for about 24 hours. After termination of the reaction, 15 mL of MeOH and 30 mL, of 1120 were added thereto, followed by extraction three times with 30 mL of MC. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 1.41 g of Intermediate I-2 (Yield: 91%). This compound was identified using MS/FAB.

C 16 H 10 O 2 : calc. 234.07, found 234.11.

Synthesis of Intermediate I-3

1.41 g (6.0 mmol) of Intermediate I-2 was dissolved in 20 mL of toluene and 20 mL of a 30% potassium phosphate solution, and then 2.03 g (7.2 mmol) of trifluoromethane sulfonic anhydride was slowly dropwise added thereto at about 0° C. The temperature of the resulting reaction solution was increased to room temperature and stirred for about 3 hours, followed by adding 30 mL of water and extraction three times with 30 mL of ethyl ether. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 1.63 g of Intermediate I-3 (Yield: 81%). This compound was identified using MS/FAB.

C 17 H 9 F 3 O 4 S: calc. 336.02, found 336.0.

Synthesis of Intermediate 3-A

7.38 g (20.0 mmol) of 3-iodo-9-phenyl-9H-carbazole, 6.27 g (30.0 mmol) of 9,9-dimethyl-9H-fluorene-2-amine, 0.37 g (0.4 mmol) of Pd 2 (dba) 3 , 0.08 g (0.4 mmol) of PtBu 3 , and 2.88 g (30.0 mmol) of KOtBu were dissolved in 60 mL of toluene and then stirred at about 85° C. for about 4 hours. The resulting reaction solution was cooled down to room temperature, followed by adding 50 mL of water and extraction three times with 50 mL of diethyl ether. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 7.92 g of Intermediate 3-A (Yield: 88%). This compound was identified using MS/FAB.

C 33 H 26 N 2 : calc. 450.20, found 450.22.

Synthesis of Compound 3

6.75 g (15.0 mmol) of Intermediate 3-A, 5.04 g (15.0 mmol) of Intermediate I-3, 0.18 g (0.2 mmol) of Pd 2 (dba) 3 , 0.04 g (0.4 mmol) of PtBu 3 , and 1.44 g (15.0 mmol) of KOtBu were dissolved in 80 mL of toluene, and then stirred at about 85° C. for about 4 hours. The resulting reaction solution was cooled down to room temperature, followed by adding 50 mL of water and extraction three times with 50 mL of diethyl ether. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 8.19 g of Compound 3 (Yield: 82%). This compound was identified using MS/FAB and 1 H nuclear magnetic resonance spectroscopy (NMR).

C 49 H 34 N 2 O: calc. 666.82, found 666.85.

Synthesis Example 2: Synthesis of Compound 21

Compound 21 was synthesized in the same manner as in Synthesis Example 1, except that Intermediate 21-A, instead of Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, was used. This compound was identified using MS/FAB and 1 H NMR.

C 50 H 32 N 2 O: calc. 676.81, found 676.86.

Synthesis Example 3: Synthesis of Compound 29

Synthesis of Intermediate I-4

16.0 g (100 mmol) of 1,5-dihydroxynaphthalene was dissolved in 60 mL of dimethyl sulfoxide (DMSO), and 15.2 g (110 mmol) of K 2 CO 3 and 22.4 g (110 mmol) of iodomethane were dropwise added thereto at about 0° C. The temperature of the resulting reaction solution was increased to room temperature and stirred at room temperature for about 24 hours. After termination of the reaction, 60 mL of H 2 O was added, followed by extraction three times with 60 mL of MC. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 10.1 g of Intermediate I-4 (Yield: 58%). This compound was identified using MS/FAB.

C 11 H 10 O 2 : calc. 174.19, found 174.23.

Synthesis of Intermediate I-5

Intermediate I-5 was synthesized in the same manner as in the synthesis of Intermediate I-1 in Synthesis Example 1, except that Intermediate I-4 and 1-bromo-2-iodobenzene, instead of 1-naphthol and 2-bromo-1-iodo-4-methoxybenzene, respectively, used in the synthesis of Intermediate I-1 in Synthesis Example 1, were used. This compound was identified using MS/FAB.

C 17 H 12 O 2 : calc. 248.18, found 248.19.

Synthesis of Intermediate I-6

Intermediate I-6 was synthesized in the same manner as in the synthesis of Intermediate I-2 in Synthesis Example 1, except that Intermediate I-5, instead of Intermediate I-1 used in the synthesis of Intermediate I-2 in Synthesis Example 1, was used. This compound was identified using MS/FAB.

C 16 H 10 O 2 : calc. 234.25, found 234.26.

›EXAMPLE · 2 of 5

Synthesis of Intermediate I-7

Intermediate I-7 was synthesized in the same manner as in the synthesis of Intermediate I-3 in Synthesis Example 1, except that Intermediate I-6, instead of Intermediate I-2 used in the synthesis of Intermediate I-3 in Synthesis Example 1, was used. This compound was identified using MS/FAB.

C 17 H 9 F 3 O 4 S: calc. 336.02, found 336.0.

Synthesis of Intermediate 29-A

4.61 g (20.0 mmol) of 3-bromo-4-nitroanisole, 3.44 g (21.0 mmol) of 1-naphthaleneboronic acid, 0.29 g (0.25 mmol) of Pd(PPh 3 ) 4 , and 4.15 g (35.0 mmol) of K 2 CO 3 were dissolved in 60 mL of a mixed solution of tetrahydrofuran (THF) and water (H 2 O) (2:1 by volume), and stirred at about 70° C. for about 5 hours. The resulting reaction solution was cooled down to room temperature, followed by extraction three times with 50 mL of water and 50 mL of diethyl ether. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 4.91 g of Intermediate 29-A (Yield: 88%). This compound was identified using MS/FAB.

C 17 H 13 NO 3 : calc. 279.29, found 279.30.

Synthesis of Intermediate 29-B

200 mL of 1,2-dichlorobenzene was dissolved in 4.91 g (17.5 mmol) of Intermediate 29-A, and 6.89 g (26.3 mmol) of triphenylphosphine was added thereto and stirred at about 150° C. for about 12 hours. The resulting reaction solution was cooled down to room temperature and followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 3.50 g of Intermediate 29-B (Yield: 81%). This compound was identified using MS/FAB.

C 17 H 13 NO: calc. 247.29, found 247.31.

Synthesis of Intermediate 29-C

3.50 g (14.2 mmol) of Intermediate 29-B, 5.77 g (28.3 mmol) of iodobenzene, 270 mg (0.142 mmol) of CuI, 5.89 g (42.6 mmol) of K 2 CO 3 , and 75 mg (0.28 mmol) of 18-Crown-6 ether were dissolved in 100 mL of 1,2-dichlorobenzene and stirred at about 150° C. for about 12 hours. The resulting reaction solution was cooled down to room temperature and followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 3.62 g of Intermediate 29-C(Yield: 79%). This compound was identified using MS/FAB.

C 23 H 17 NO: calc. 323.39, found 323.40.

Synthesis of Intermediate 29-D

Intermediate 29-D was synthesized in the same manner as in the synthesis of Intermediate I-2 in Synthesis Example 1, except that Intermediate 29-C, instead of Intermediate I-1 used in the synthesis of Intermediate I-2 in Synthesis Example 1, was used. This compound was identified using MS/FAB.

C 22 H 15 NO: calc. 309.36, found 309.38.

Synthesis of Intermediate 29-E

Intermediate 29-E was synthesized in the same manner as in the synthesis of Intermediate I-3 in Synthesis Example 1, except that Intermediate 29-D, instead of Intermediate I-2 used in the synthesis of Intermediate I-3 in Synthesis Example 1, was used. This compound was identified using MS/FAB.

C 23 H 14 F 3 NO 3 S: calc. 441.42, found 441.44.

Synthesis of Intermediate 29-F

Intermediate 29-F was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 4-aminobenzonitrile and Intermediate 29-E, respectively, instead of Intermediate 3-A and Intermediate I-3 used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB.

C 29 H 19 N 3 : calc. 409.49, found 409.51.

Synthesis of Compound 29

Compound 29 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 29-F and Intermediate I-7, respectively, instead of Intermediate 3-A and Intermediate I-3 used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 45 H 27 N 3 O: calc. 625.73, found 625.76.

Synthesis Example 4: Synthesis of Compound 40

Compound 40 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 40-A, instead of Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, was used. This compound was identified using MS/FAB and 1 H NMR.

C 46 H 30 N 2 O: calc. 626.23, found 626.26.

Synthesis Example 5: Synthesis of Compound 49

Compound 49 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate I-7 and Intermediate 49-A, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 55 H 38 N 2 O: calc. 742.92, found 742.94.

Synthesis Example 6: Synthesis of Compound 56

Synthesis of Intermediate 56-A

3.69 g (10.0 mmol) of 3-iodo-9-phenyl-9H-carbazole, 2.54 g (10.0 mmol) of bis(pinacolato)diborone, 0.36 g (0.5 mmol) of PdCl 2 (dppf) 2 , and 2.94 g (30.0 mmol) of KOAc were dissolved in 40 mL of DMSO, and stirred at about 80° C. for about 6 hours. The resulting reaction solution was cooled down to room temperature, followed by adding 50 mL of water and extraction three times with 50 mL of diethyl ether. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 3.37 g of Intermediate 56-A (Yield: 80%). This compound was identified using MS/FAB.

C 24 H 24 BNO 2 : calc. 369.27, found 369.29.

Synthesis of Intermediate 56-B

2.11 g (5.0 mmol) of Intermediate 56-A, 0.91 g (5.0 mmol) of 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene, 0.29 g (0.25 mmol) of Pd(PPh 3 ) 4 , and 2.07 g (15.0 mmol) of K 2 CO 3 were dissolved in 60 mL of a mixed solution of THF and H 2 O (2:1 by volume) and stirred at about 70° C. for about 5 hours. The resulting reaction solution was cooled down to room temperature, followed by adding 50 mL of water and extraction three times with 50 mL of diethyl ether. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified using silica gel column chromatography to obtain 1.71 g of Intermediate 56-B (Yield: 86%). This compound was identified using MS/FAB

›EXAMPLE · 3 of 5

C 33 H 24 BrN: calc. 514.46, found 514.48.

Synthesis of Intermediate I-8

Intermediate I-8 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that aniline, instead of Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, was used. This compound was identified using MS/FAB.

C 22 H 15 NO: calc. 309.36, found 309.38.

Synthesis of Compound 56

Compound 56 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 56-B and Intermediate I-8, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H-NMR.

C 55 H 38 N 2 O: calc. 742.29, found 742.31.

Synthesis Example 7: Synthesis of Compound 57

Compound 57 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 57-A and Intermediate I-9, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 46 H 29 FN 2 O: calc. 644.74, found 644.76.

Synthesis Example 8: Synthesis of Compound 59

Compound 59 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 57-A and Intermediate I-10, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 52 H 34 N 2 O: calc. 702.85, found 702.87.

Synthesis Example 9: Synthesis of Compound 62

Compound 62 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 57-A and Intermediate I-11, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 55 H 38 N 2 O: calc. 742.92, found 742.93.

Synthesis Example 10: Synthesis of Compound 63

Compound 63 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 57-A and Intermediate I-12, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 52 H 32 N 2 O 2 : calc. 716.84, found 716.86.

Synthesis Example 11: Synthesis of Compound 70

Compound 70 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 70-A and Intermediate I-11, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 56 H 37 N 3 O: calc. 767.93, found 767.94.

Synthesis Example 12: Synthesis of Compound 74

Compound 74 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 74-A and Intermediate I-13, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 61 H 42 N 2 O: calc. 819.02, found 819.06.

Synthesis Example 13: Synthesis of Compound 78

Synthesis of Intermediate I-14

Intermediate I-14 was synthesized in the same manner as in the synthesis of Intermediate 56-A in Synthesis Example 6, except that Intermediate I-13, instead of 3-iodo-9-phenyl-9H-carbazole used in the synthesis of Intermediate 56-A in Synthesis Example 6, was used. This compound was identified using MS/FAB.

C 22 H 21 BO 3 : calc. 344.21, found 344.23.

Synthesis of Intermediate I-15

Intermediate I-15 was synthesized in the same manner as in the synthesis of Intermediate 56-B in Synthesis Example 6, except that Intermediate I-14, instead of 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene used in the synthesis of Intermediate 56-B in Synthesis Example 6, was used. This compound was identified using MS/FAB.

C 22 H 13 BrO: calc. 373.24, found 373.26.

Synthesis of Intermediate I-16

Intermediate I-16 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 4-fluoroaniline and Intermediate I-15, respectively, instead of Intermediate 3-A and Intermediate I-3 used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB.

C 28 H 18 FNO: calc. 403.45, found 403.46.

Synthesis of Compound 78

Compound 78 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 3-iodo-9-phenyl-9H-carbazole and Intermediate I-16, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 46 H 29 FN 2 O: calc. 644.74, found 644.76.

Synthesis Example 14: Synthesis of Compound 85

Compound 85 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 9-(4-fluorophenyl)-3-iodo-9H-carbazole and Intermediate I-17, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 52 H 33 FN 2 O: calc. 720.84, found 720.86.

Synthesis Example 15: Synthesis of Compound 89

Compound 89 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 9-(9,9-dimethyl-9H-2-fluorene-2-yl)-3-iodo-9H-carbazole and Intermediate I-18, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 61 H 42 N 2 O: calc. 819.02, found 819.03.

Synthesis Example 16: Synthesis of Compound 90

›EXAMPLE · 4 of 5

Compound 90 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 57-A and Intermediate I-17, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 58 H 38 N 2 O: calc. 778.95, found 778.97.

Synthesis Example 17: Synthesis of Compound 98

Compound 90 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 98-A and Intermediate I-19, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 58 H 38 N 2 O: calc. 778.95, found 778.96.

Synthesis Example 18: Synthesis of Compound 102

Compound 102 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 2-iodo-9-phenyl-9H-carbazole and Intermediate I-17, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 52 H 34 N 2 O: calc. 702.85, found 702.87.

Synthesis Example 19: Synthesis of Compound 106

Compound 106 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 106-A and Intermediate I-20, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 65 H 42 N 2 O: calc. 867.06, found 867.09.

Synthesis Example 20: Synthesis of Compound 110

Compound 110 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 110-A and Intermediate I-18, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

C 64 H 42 N 2 O: calc. 855.05, found 855.07.

Synthesis Example 21: Synthesis of Compound 6

Compound 6 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 6-A, instead of Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, was used. This compound was identified using MS/FAB and 1 H NMR.

Synthesis Example 22: Synthesis of Compound 7

Compound 7 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 7-A, instead of Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, was used. This compound was identified using MS/FAB and 1 H NMR.

Synthesis Example 23: Synthesis of Compound 12

Compound 12 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 12-A and Intermediate I-7, respectively, instead of Intermediate 3-A and Intermediate I-3 used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

Synthesis Example 24: Synthesis of Compound 24

Synthesis of Intermediate 24-F

Intermediate 24-F was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 9,9-dimethyl-9H-fluorene-2-amine and Intermediate 29-E, respectively, instead of Intermediate 3-A and Intermediate I-3 used in the synthesis of Compound 3 in Synthesis Example 1, were used.

Synthesis of Compound 24

Compound 24 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 24-F, instead of Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, was used. This compound was identified using MS/FAB and 1 H NMR.

Synthesis Example 25: Synthesis of Compound 33

Synthesis of Intermediate 23-F

Intermediate 33-F was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 2-aminodibenzothiophene and Intermediate 29-E, respectively, instead of Intermediate 3-A and Intermediate I-3 used in the synthesis of Compound 3 in Synthesis Example 1, were used.

Synthesis of Compound 33

Compound 33 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 33-F, instead of Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, was used. This compound was identified using MS/FAB and 1 H NMR.

Synthesis Example 26: Synthesis of Compound 43

Compound 43 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 43-A, instead of Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, was used. This compound was identified using MS/FAB and 1 H NMR.

Synthesis Example 27: Synthesis of Compound 52

Compound 52 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that Intermediate 57-A and Intermediate I-8, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

Synthesis Example 28: Synthesis of Compound 81

Synthesis of Intermediate I-21

Intermediate I-21 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 2-aminodibenzofuran and Intermediate I-15, respectively, instead of Intermediate 3-A and Intermediate I-3 used in the synthesis of Compound 3 in Synthesis Example 1, were used.

Synthesis of Compound 81

Compound 81 was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 3-iodo-9-phenyl-9H-carbazole and Intermediate I-21, respectively, instead of Intermediate I-3 and Intermediate 3-A used in the synthesis of Compound 3 in Synthesis Example 1, were used. This compound was identified using MS/FAB and 1 H NMR.

›EXAMPLE · 5 of 5

1 H NMR and MS/FAB data of the compounds synthesized in the above synthesis examples are shown in Table 1.

Synthetic pathways and source materials for other compounds not in Table 1 would be apparent to one of ordinary skill in the art based on the synthetic pathways and source materials in Synthesis Examples 1 to 28.

›Example 1

A 15 Ω/cm 2 ITO glass substrate (having a thickness of 1,200 Å, available from Corning) was cut to a size of 50 mm×50 mm×0.7 mm and then sonicated in isopropyl alcohol and pure water each for five minutes, and then cleaned by irradiation of ultraviolet rays for 30 minutes and exposure to ozone. The resulting glass substrate with an ITO anode was mounted into a vacuum deposition device.

2-TNATA was vacuum-deposited on the ITO anode of the glass substrate to form an HIL having a thickness of 600 Å, and Compound 3 was deposited on the HIL to form a HTL having a thickness of about 300 Å, thus forming a hole transport region.

9,10-di-naphthalene-2-yl-anthracene (ADN) as a host and N,N,N′,N′-tetraphenyl-pyrene-1,6-diamine (TPD) (as Compound FD1) as a dopant were co-deposited on the hole transport region in a weight ratio of about 98:2 to form an EMI, having a thickness of about 300 Å.

Alq 3 was then deposited on the EML to form an ETL having a thickness of about 300 Å, and then LiF was deposited on the ETL to form an EIL having a thickness of about 10 Å, thus forming an electron transport region.

Subsequently, Al was vacuum-deposited on the electron transport region to form a cathode having a thickness of about 3,000 Å, thereby completing the manufacture of an organic light-emitting device.

›Example 2 to 20, and Comparative Examples 1 to 3

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that the compounds in Table 2, instead of Compound 3 used in Example 1, were used, respectively.

Evaluation Example 1

Driving voltages, current densities, luminance, efficiency, and half-lifetimes of the organic light-emitting devices of Examples 1 to 20 and Comparative Examples 1 to 3 were evaluated using a Keithley Source-Measure Unit (SMU 236) and a PR650 Spectroscan available from Photo Research, Inc. The results are shown in Table 2. A half-lifetime was measured as the time taken until a measured initial luminance (assumed as 100%) is reduced to 50%.

As described above, according to the one or more embodiments of the present disclosure, an organic light-emitting device including an amine-based compound of Formula 1 may have a low driving voltage, an improved efficiency, improved luminance and long lifespan.

Example embodiments have been disclosed herein, and although specific terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purpose of limitation. In some instances, as would be apparent to one of ordinary skill in the art as of the filing of the present application, features, characteristics, and/or elements described in connection with a particular embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of skill in the art that various changes in form and details may be made without departing from the spirit and scope thereof as set forth in the following claims.

›Tables in the description — 2

TABLE 1

	Com-		MS/FAB	Yield
pound	1 H NMR (CDCl 3 , 400 MHz)	found	calc.	(%)
3	δ = 8.25 − 8.22 (m, 2H), 7.83 − 7.80	666.85	666.82	82
	(m, 1H), 7.76 − 7.70
	(m, 2H), 7.61 − 7.55 (m, 3H),
	7.53 − 7.47 (m, 6H), 7.40 −
	7.20 (m, 7H), 7.13 − 7.05 (m, 3H),
	6.91 (dd, 1H), 6.71
	(d, 1H), 6.58 − 6.52 (m, 2H), 1.52 (s, 6H)
6	δ = 8.50 − 8.48 (m, 3H), 7.55	715.87	715.85	76
	(d, 1H), 7.53 − 7.34 (m,
	25H), 6.81 (m, 1H), 6.70 − 6.65 (m, 3H)
7	δ = 8.35 − 8.30 (m, 2H),	640.76	640.74	79
	7.78 − 7.28 (m, 22H), 7.15 (m,
	1H), 6.83 (m, 1H), 6.63 − 6.60 (m, 2H)
12	δ = 8.41 − 8.39 (m, 1H), 8.12 − 8.07	568.66	568.65	85
	(m, 1H), 7.79 − 7.75
	(m, 1H), 7.65 − 7.60 (m, 1H),
	7.50 − 7.23 (m, 15H), 6.89 −
	6.84 (m, 4H), 6.50 − 6.45 (m, 2H)
21	δ = 8.43 − 8.41 (m, 2H), 8.12 − 8.07	676.86	676.81	88
	(m, 1H), 7.78 − 7.76
	(m, 1H), 7.60 − 7.14 (m, 22H),
	7.08 − 7.06 (m, 1H), 6.85 −
	6.80 (m, 3H), 6.65 − 6.62 (m, 2H)
24	δ = 8.25 − 8.20 (m, 2H), 8.05 (d, 1H),	716.89	716.88	81
	7.92 − 7.88 (m, 2H),
	7.77 − 7.70 (m, 3H), 7.60 − 7.30
	(m, 14H), 7.20 − 7.18 (m,
	1H), 7.13 − 7.10 (m, 2H), 7.07 (dd, 1H),
	6.58 − 6.55 (m, 2H), 1.59 (s, 6H)
29	δ = 8.43 (d, 1H), 8.25 (d, 1H),	625.76	625.73	74
	8.06 (d, 1H), 7.88 (d,
	1H), 7.80 − 7.73 (m, 2H),
	7.64 − 7.61 (m, 1H), 7.55 − 7.48
	(m, 6H), 7.45 − 7.28 (m, 9H),
	7.11 − 7.09 (m, 1H), 6.92 −
	6.88 (m, 2H), 6.76 − 6.72 (m, 2H)
33	δ = 8.43 (d, 1H), 8.23 (d, 1H),	706.88	706.86	80
	8.06 (d, 1H), 7.90 − 7.70
	(m, 6H), 7.63 − 7.48 (m, 9H),
	7.45 − 777.30 (m, 8H),
	7.13 − 7.10 (m, 1H), 6.90 − 6.85
	(m, 2H), 6.76 (dd, 1H)
40	δ = 8.25 − 8.20 (m, 1H), 8.17 − 8.10	626.26	626.75	77
	(m, 1H), 7.74 (d, 1H),
	7.67 (d, 1H), 7.60 − 7.43 (m, 14H),
	7.38 − 7.28 (m, 5H),
	7.25 − 7.20 (m, 2H), 7.04 (dd, 1H),
	6.98 − 6.97 (m, 1H),
	6.92 − 6.88 (m, 2H), 6.68 − 6.63 (m, 2H)
43	δ = 8.25 − 8.20 (m, 1H), 8.17 − 8.10	666.84	666.83	76
	(m, 1H), 7.78 − 7.70
	(m, 3H), 7.60 − 7.55 (m, 3H),
	7.53 − 7.46 (m, 6H), 7.38 −
	7.28 (m, 5H), 7.25 − 7.20 (m, 2H),
	7.12 − 7.10 (m, 2H),
	7.08 − 6.97 (m, 2H), 6.77 (d, 1H),
	6.65 − 6.60 (m, 2H),
	1.59 (s, 6H)
49	δ = 8.43 (dd, 1H), 8.17 − 8.14	742.94	742.92	72
	(m, 1H), 7.80 − 7.70 (m,
	3H), 7.63 − 7.58 (m, 3H),
	7.50 − 7.29 (m, 16H), 7.26 − 7.24
	(m, 1H), 7.13 − 7.10 (m, 3H),
	6.78 − 6.74 (m, 2H), 6.62
	(d, 1H), 6.58 (d, 1H), 1.52 (s, 6H)
52	δ = 8.25 − 8.20 (m, 2H), 8.06 − 8.04	626.77	626.75	81
	(m, 1H), 7.77 − 7.75
	(m, 1H), 7.69 − 7.45 (m, 12H),
	7.38 − 7.25 (m, 3H), 7.22 −
	7.19 (m, 2H), 7.06 − 7.02 (m, 2H),
	6.74 − 6.70 (m, 3H),
	6.63 − 6.60 (m, 1H), 6.56 (d, 1H),
	6.36 − 6.32 (m, 2H)
56	δ = 8.25 − 8.20 (m, 2H), 8.06 − 8.04	742.31	742.92	73
	(m, 1H), 7.90 − 7.88
	(m, 1H), 7.80 − 7.78 (m, 1H),
	7.71 − 7.68 (m, 2H), 7.60 −
	7.54 (m, 4H), 7.52 − 7.42
	(m, 6H), 7.38 − 7.25 (m, 3H),
	7.22 − 7.18 (m, 2H), 7.11 − 7.05
	(m, 3H), 6.65 − 6.62 (m,
	3H), 6.57 − 6.52 (m, 2H), 6.38 − 6.35
	(m, 2H), 1.53 (s, 6H)
57	δ = 8.25 − 8.20 (m, 2H), 8.06 − 8.04	644.76	644.74	77
	(m, 1H), 7.75 − 7.73
	(m, 1H), 7.68 − 7.45 (m, 12H),
	7.39 − 7.26 (m, 3H), 7.22 −
	7.18 (m, 2H), 6.96 − 6.92 (m, 2H),
	6.78 − 6.73 (m, 3H),
	6.69 − 6.65 (m, 2H), 6.53 (d, 1H)
59	δ = 8.25 − 8.20 (m, 2H), 8.06 − 8.04	702.87	702.26	74
	(m, 1H), 7.75 − 7.73
	(m, 1H), 7.68 − 7.55 (m, 9H), 7.52 −
	7.44 (m, 8H), 7.40 −
	7.25 (m, 5H), 7.21 − 7.19 (m, 2H),
	6.78 − 6.69 (m, 5H), 6.54 (d, 1H)
62	δ = 8.25 − 8.20 (m, 2H), 8.06 − 8.04	742.93	742.92	82
	(m, 1H), 7.78 − 7.73
	(m, 2H), 7.70 − 7.65 (m, 2H),
	7.60 − 7.55 (m, 5H), 7.52 −
	7.45 (m, 6H), 7.38 − 7.26
	(m, 4H), 7.23 − 7.19 (m, 2H),
	7.13 − 7.10 (m, 2H), 6.89 (d, 1H),
	6.71 − 6.68 (m, 3H),
	6.55 − 6.52 (m, 2H), 1.53 (s, 6H),
63	δ = 8.25 − 8.20 (m, 2H), 8.06 − 8.04	716.86	716.84	86
	(m, 1H), 7.85 − 7.83
	(m, 1H), 7.75 − 7.72 (m, 1H),
	7.69 − 7.66 (m, 2H), 7.60 −
	7.45 (m, 12H), 7.42 − 7.28
	(m, 6H), 7.23 − 7.18 (m, 2H),
	7.05 (dd, 1H), 6.84 − 6.78
	(m, 3H), 6.59 (dd, 1H)
70	δ = 8.25 − 8.20 (m, 2H), 8.06 − 8.04	767.94	767.93	89
	(m, 1H), 7.85 − 7.82
	(m, 2H), 7.78 − 7.73 (m, 2H),
	7.68 − 7.62 (m, 2H), 7.60 −
	7.55 (m, 7H), 7.52 − 7.45 (m, 2H),
	7.38 − 7.28 (m, 3H),
	7.22 − 7.18 (m, 2H), 7.15 − 7.10
	(m, 2H), 6.84 (dd, 1H),
	6.70 − 6.66 (m, 3H), 6.56 − 6.52
	(m, 2H), 1.53 (s, 6H),
74	δ = 8.46 − 8.42 (m, 1H), 8.26 − 8.22	819.06	819.02	85
	(m, 1H), 8.06 − 8.04
	(m, 1H), 7.80 − 7.74 (m, 3H),
	7.68 − 7.52 (m, 6H), 7.50 −
	7.25 (m, 15H), 7.21 − 7.19 (m, 1H),
	7.13 − 7.10 (m, 3H),
	6.72 (d, 1H), 6.66 (dd, 1H),
	6.52 − 6.49 (m, 2H), 6.45 −
	6.44 (m, 1H), 1.52 (s, 6H),
78	δ = 8.22 − 8.19 (m, 1H), 8.16 − 8.13	644.76	644.74	84
	(m, 1H), 7.90 − 7.88
	(m, 1H), 7.60 − 7.54 (m, 3H),
	7.52 − 7.48 (m, 6H), 7.44 −
	7.35 (m, 6H), 7.32 − 7.22 (m, 3H),
	7.08 − 7.05 (m, 1H),
	6.98 − 6.90 (m, 2H), 6.65 − 6.58 (m, 5H)
81	δ = 8.22 − 8.20 (m, 1H), 8.16 − 8.10	716.86	716.84	82
	(m, 1H), 7.88 (d, 1H),
	7.84 − 7.80 (m, 1H), 7.60 − 7.22
	(m, 23H), 7.08 − 7.06 (m,
	1H), 6.96 (dd, 1H), 6.70 − 6.65
	(m, 2H), 6.60 (dd, 1H)
85	δ = 8.22 − 8.20 (m, 1H), 8.16 − 8.10	720.86	720.84	82
	(m, 1H), 7.89 (d, 1H),
	7.61 − 7.56 (m, 5H), 7.52 − 7.30
	(m, 15H), 7.28 − 7.24 (m,
	2H), 7.10 − 7.06 (m, 3H),
	6.67 − 6.54 (m, 5H)
89	δ = 8.42 − 8.40 (m, 1H), 8.26 − 8.22	819.03	819.02	76
	(m, 1H), 7.92 (d, 1H),
	7.86 − 7.84 (m, 1H), 7.63 − 7.55
	(m, 3H), 7.52 − 7.06 (m,
	24H), 6.68 − 6.65 (m, 2H), 6.60 − 6.56
	(m, 3H), 1.52 (s, 6H),
90	δ = 8.25 − 8.22 (m, 1H), 8.15 − 8.13	778.97	778.95	74
	(m, 1H), 8.07 − 8.05
	(m, 1H), 7.89 (d, 1H), 7.76
	(d, 1H), 7.65 (dd, 1H),
	7.60 − 7.25 (m, 24H), 7.22 − 7.20
	(m, 1H), 7.07 − 7.04 (m,
	1H), 6.85 − 6.80 (m, 2H),
	6.65 − 6.55 (m, 4H),
98	δ = 8.46 − 8.44 (m, 1H), 8.23	778.96	778.95	73
	(t, 1H), 8.10 − 8.08 (m, 1H),
	7.94 − 7.85 (m, 3H), 7.76 − 7.27
	(m, 20H), 7.21 − 7.19 (m,
	1H), 7.09 − 7.02 (m, 3H),
	7.22 − 7.20 (m, 1H), 7.07 − 7.04
	(m, 1H), 6.96 − 6.92 (m, 1H),
	6.85 − 6.81 (m, 2H), 6.68 −
	6.62 (m, 1H), 6.23 − 6.20 (m, 2H),
102	δ = 8.18 − 8.12 (m, 2H), 7.90 − 7.85	702.87	702.85	71
	(m, 1H), 7.75 − 7.72
	(m, 1H), 7.60 − 7.27 (m, 22H),
	7.25 − 7.23 (m, 1H), 7.07 −
	7.04 (m, 1H), 7.02 − 7.00 (m, 1H),
	6.59 (dd, 1H), 6.80 − 6.75 (m, 4H)
106	δ = 8.25 − 8.20 (m, 1H), 8.14 − 8.12	867.09	867.06	72
	(m, 1H), 7.86 − 7.79
	(m, 3H), 7.68 (d, 1H), 7.60 − 7.54
	(m, 3H), 7.52 − 7.10
	(m, 26H), 6.86 − 6.79 (m, 4H), 6.70 − 6.68
	(m, 1H), 6.57 − 6.52 (m, 2H)
110	δ = 8.43 − 8.40 (m, 1H), 8.27 − 8.24	855.07	855.05	70
	(m, 1H), 8.15 − 8.13
	(m, 1H), 7.93 − 7.91 (m, 1H),
	7.85 − 7.80 (m, 2H), 7.63 −
	7.55 (m, 5H), 7.55 − 7.28 (m, 23H),
	7.20 − 7.18 (m, 1H),
	7.08 − 7.05 (m, 1H), 6.97 − 6.93
	(m, 2H), 6.85 − 6.82 (m,
	2H), 6.75 − 6.72 (m, 2H)

TABLE 2

		Driving	Current				Half-lifetime
		voltage	density	Luminance	Efficiency	Emission	(hr)
Example	HTL material	(V)	(mA/cm 2 )	(cd/m 2 )	(cd/A)	color	@50 mA/cm 2
Example 1	Compound 3	5.68	50	3080	6.16	blue	305
Example 2	Compound	5.65	50	3085	6.17	blue	308
	21
Example 3	Compound	5.70	50	3082	6.16	blue	312
	29
Example 4	Compound	5.65	50	3095	6.19	blue	300
	40
Example 5	Compound	5.64	50	3110	6.42	blue	315
	49
Example 6	Compound	5.42	50	3190	6.22	blue	325
	56
Example 7	Compound	5.43	50	3220	6.44	blue	329
	57
Example 8	Compound	5.40	50	3250	6.50	blue	340
	59
Example 9	Compound	5.42	50	3330	6.66	blue	355
	62
Example 10	Compound	5.50	50	3280	6.56	blue	335
	63
Example 11	Compound	5.50	50	3220	6.44	blue	370
	70
Example 12	Compound	5.45	50	3215	6.43	blue	340
	74
Example 13	Compound	5.51	50	3220	6.44	blue	325
	78
Example 14	Compound	5.53	50	3218	6.43	blue	330
	85
Example 15	Compound	5.53	50	3220	6.44	blue	335
	89
Example 16	Compound	5.51	50	3215	6.43	blue	350
	90
Example 17	Compound	5.60	50	3200	6.40	blue	338
	98
Example 18	Compound	5.55	50	3290	6.58	blue	330
	102
Example 19	Compound	5.60	50	3210	6.42	blue	325
	106
Example 20	Compound	5.57	50	3200	6.40	blue	340
	110
Comparative	NPB	7.01	50	2645	5.29	blue	258
Example 1
Comparative	Compound A	6.56	50	2720	5.44	blue	240
Example 2
Comparative	Compound B	6.46	50	2845	5.69	blue	234
Example 3

Claims as granted

20 claims

Classifications

6 codes

IPC · International Patent Classification

Section C — Chemistry; metallurgy

C07D405/14
C07C211/54
C07D409/14
C07D405/12
C09K11/06

Section H — Electricity

H10K99/00

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Pendency

2.6 y

950 days filing → grant

Office actions

after a restriction

Examiner

Mike M Dollinger

art unit 1766 · TC 1700

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Citations: 9 back · 6 forward

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