Oligomer, composition and composite material employing the same

0.045 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 10 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.604 mol of 1-hexene (as α-olefin), 73.6 g of vinyl norbornene, and 128 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (57.7 g of norbornene (NB) dissolved in 50 ml of toluene) was added into the second reaction bottle. Herein, α-olefin (1-hexene) had a molar percentage of 50 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 63 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (I) was obtained, wherein the ratio of the repeat unit

to the repeat unit

of Copolymer (I) was about 1:1.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (I) were determined, and the results are shown in Table 1.

0.045 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 10 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.362 mol of 1-hexene (α-olefin), 73.6 g of vinyl norbornene, and 128 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (57.7 g of norbornene dissolved in 50 ml of toluene) was added into the second reaction bottle. Herein, α-olefin (1-hexene) had a molar percentage of 30 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 63 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (II) was obtained, wherein the ratio of the repeat unit

to the repeat unit

of Copolymer (II) was about 1:1.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (II) were determined, and the results are shown in Table 1.

0.09 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 15 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.483 mol of 1-hexene (α-olefin), 147 g of vinyl norbornene, and 260 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (115 g of norbornene dissolved in 100 ml of toluene) was added into the second reaction bottle. Herein, α-olefin (1-hexene) had a molar percentage of 20 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 125 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (III) was obtained, wherein the ratio of the repeat unit

to the repeat unit

of Copolymer (III) was about 1:1.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (III) were determined, and the results are shown in Table 1.

0.045 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 10 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.241 mol of 1-hexene (α-olefin), 52.1 g of vinyl norbornene, and 87 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (75 g of norbornene dissolved in 90 ml of toluene) was added into the second reaction bottle. Herein, α-olefin (1-hexene) had a molar percentage of 20 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 63 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (IV) was obtained, wherein the ratio of the repeat unit

to the repeat unit of Copolymer (IV) was about 1:0.5.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (IV) were determined, and the results are shown in Table 1.

0.054 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 15 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.145 mol of 1-hexene (α-olefin), 88.3 g of vinyl norbornene, and 150 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (69.3 g of norbornene dissolved in 60 ml of toluene) was added into the second reaction bottle. Herein, α-olefin (1-hexene) had a molar percentage of 10 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 75 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (V) was obtained, wherein the ratio of the repeat unit

to the repeat unit

of Copolymer (V) was about 1:1.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (V) were determined, and the results are shown in Table 1.

0.018 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 10 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.0245 mol of 1-hexene (α-olefin), 29.4 g of vinyl norbornene, and 45 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (23.06 g of norbornene dissolved in 20 ml of toluene) was added into the second reaction bottle. Herein, α-olefin (1-hexene) had a molar percentage of 5 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 25 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (VI) was obtained, wherein the ratio of the repeat unit

to the repeat unit

of Copolymer (VI) was about 1:1.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (VI) were determined, and the results are shown in Table 1.

0.009 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, 6 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.0073 mol of 1-hexene (α-olefin), 14.7 g of vinyl norbornene, and 23 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (11.5 g of norbornene dissolved in 10 ml of toluene) was added into the second reaction bottle. Herein, α-olefin (1-hexene) had a molar percentage of 3 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 13 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (VII) was obtained, wherein the ratio of the repeat unit

to the repeat unit

of Copolymer (VII) was about 1:1.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (VII) were determined, and the results are shown in Table 1.

0.054 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, 30 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.725 mol of 1-hexene (α-olefin), 177 g of vinyl norbornene, and 300 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. Herein, α-olefin (1-hexene) had a molar percentage of 50 mol %, based on the mole of vinyl norbornene. After the reaction was complete, 75 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (VIII) was obtained, wherein the only repeat unit of Copolymer (VIII) was

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (VIII) were determined, and the results are shown in Table 1.

0.0018 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, 1 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.0005 mol of 1-hexene (α-olefin), 3 g of vinyl norbornene, and 4.5 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (2.36 g of norbornene dissolved in 2 ml of toluene) was added into the second reaction bottle. Herein, α-olefin (1-hexene) had a molar percentage of 1 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 2.5 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (IX) was obtained, wherein the ratio of the repeat unit

to the repeat unit

of Copolymer (IX) was about 1:1.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (IX) were determined, and the results are shown in Table 1.

Comparative Example 1

0.018 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 10 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.245 mol of methylacrylate (α-olefin), 29.4 g of vinyl norbornene, and 45 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (23.06 g of norbornene dissolved in 20 ml of toluene) was added into the second reaction bottle. Herein, methylacrylate had a molar percentage of 50 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 25 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (X) was obtained, wherein the ratio of the repeat unit

to the repeat unit

of Copolymer (X) was about 1:1.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (X) were determined, and the results are shown in Table 1.

Comparative Example 2

0.018 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 10 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 29.4 g of vinyl norbornene, and 35 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (23.06 g of norbornene dissolved in 20 ml of toluene) was added into the second reaction bottle. After the reaction was complete, 25 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (XI) was obtained, wherein the ratio of the repeat unit

to the repeat unit

of Copolymer (XI) was about 1:1.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (XI) were determined, and the results are shown in Table 1.

In order to meet the processing requirements for subsequently forming the film of the disclosure, the solubility of the oligomer of the disclosure in toluene should be greater or equal to 20 wt %. As shown in Table 1, when the copolymer prepared by copolymerizing vinyl norbornene, norbornene and 1-hexene (α-olefin) (i.e. the oligomer of the disclosure) has a molecular weight less than or equal to 12,000, the solubility of the oligomer of the disclosure in toluene can meet the processing requirements for subsequently forming the film of the disclosure.

0.018 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 10 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.247 mol of 1-octadecene (α-olefin), 29.4 g of vinyl norbornene, and 45 ml of toluene were added into a second reaction bottle, obtaining a metal-catalyst-containing solution. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (23.06 g of norbornene dissolved in 20 ml of toluene) was added into the second reaction bottle. Herein, α-olefin (1-octadecene) had a molar percentage of 50 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 25 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (XII) was obtained.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (XII) were determined, and the results are shown in Table 2.

Example 11 was performed in the same manner as Example 10 except that the amount of 1-octadecene was reduced from 0.247 mol to 0.049 mol, obtaining Copolymer (XIII). The number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (XIII) were determined, and the results are shown in Table 2.

Example 12 was performed in the same manner as Example 10 except that the 1-octadecene was replaced with styrene, obtaining Copolymer (XIV). The number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (XIV) were determined, and the results are shown in Table 2.

0.006 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 4 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.008 mol of vinylcyclohexene (α-olefin), 9.8 g of vinyl norbornene, and 15 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. After stirring completely, a norbornene-containing solution (7.69 g of norbornene dissolved in 7 ml of toluene) was added into the second reaction bottle. Herein, α-olefin (vinylcyclohexene) had a molar percentage of 5 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 8 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (XV) was obtained.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (XV) were determined, and the results are shown in Table 2.

0.0018 g of 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride (as metal catalyst) was added into a first reaction bottle under nitrogen atmosphere, and then 0.5 ml of toluene was added into the first reaction bottle, obtaining a metal-catalyst-containing solution. After the metal catalyst was dissolved in toluene completely, 0.043 mol of methylacrylate (α-olefin), 3 g of vinyl norbornene, and 4.5 ml of toluene were added into a second reaction bottle. Next, the metal-catalyst-containing solution in the first reaction bottle was added into the second reaction bottle. Herein, methylacrylate had a molar percentage of 85 mol %, based on the total moles of vinyl norbornene and norbornene. After the reaction was complete, 2.5 ml of ethyl vinyl ether was added into the second reaction bottle. After stirring overnight, the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (XVI) was obtained.

Next, the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (XVI) were determined, and the results are shown in Table 2.

Example 15 was performed in the same manner as Example 10 except that the 1-octadecene was replaced with allyl acetate, obtaining Copolymer (XVII). The number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (XVII) were determined, and the results are shown in Table 2.

Example 16 was performed in the same manner as Example 10 except that the 1-octadecene was replaced with 1,5-hexadiene, obtaining Copolymer (XVIII). The number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (XVIII) were determined, and the results are shown in Table 2.

As shown in Table 2, with copolymerization of vinyl norbornene and norbornene, 1-hexene (α-olefin) can be replaced with 1-octadecene, styrene, vinylcyclohexene, methylacrylate, 1,5-hexadiene, or allyl acetate. Therefore, the solubility of the obtained copolymer having a number average molecular weight less than or equal to 12,000 (i.e. the oligomer of the disclosure) in toluene can also meet the requirements of the subsequent coating (or immersion) process.

Copolymer (I) (40 parts by weight) of Example 1, polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000 (with a molecular weight of about 2,300) (60 parts by weight), and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (60 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 100° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (I). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (I) were measured at 10 GHz, and the results are shown in Table 4.

Example 18 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (III) of Example 3, obtaining Film (II). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (II) were measured at 10 GHz, and the results are shown in Table 4.

Example 19 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (IV) of Example 4, obtaining Film (III). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (III) were measured at 10 GHz, and the results are shown in Table 4.

Example 20 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (V) of Example 5, obtaining Film (IV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (IV) were measured at 10 GHz, and the results are shown in Table 4.

Example 21 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (VI) of Example 6, obtaining Film (V). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (V) were measured at 10 GHz, and the results are shown in Table 4.

Example 22 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (VIII) of Example 8, obtaining Film (VI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (VI) were measured at 10 GHz, and the results are shown in Table 4.

Example 23 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (IX) of Example 9, obtaining Film (VII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (VII) were measured at 10 GHz, and the results are shown in Table 4.

Example 24 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XII) of Example 10, obtaining Film (VIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (VIII) were measured at 10 GHz, and the results are shown in Table 4.

Example 25 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XIII) of Example 11, obtaining Film (IX). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (IX) were measured at 10 GHz, and the results are shown in Table 4.

Example 26 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XIV) of Example 12, obtaining Film (X). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (X) were measured at 10 GHz, and the results are shown in Table 4.

Example 27 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XV) of Example 13, obtaining Film (XI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XI) were measured at 10 GHz, and the results are shown in Table 4.

Example 28 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVI) of Example 14, obtaining Film (XII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XII) were measured at 10 GHz, and the results are shown in Table 4.

Example 29 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVII) of Example 15, obtaining Film (XIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XIII) were measured at 10 GHz, and the results are shown in Table 4.

Example 30 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVIII) of Example 16, obtaining Film (XIV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XIV) were measured at 10 GHz, and the results are shown in Table 4.

Comparative Example 3

1,3,5-tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (TAIC) (40 parts by weight), polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000 (with a molecular weight of about 2,300) (60 parts by weight), and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (50 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 100° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XV) were measured at 10 GHz, and the results are shown in Table 4.

Copolymer (I) (31 parts by weight) of Example 1, polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000 (with a molecular weight of about 2,300) (46 parts by weight), polystyrene-butadiene-styrene (SBS, manufactured by Cray Valley with a trade No. of Ricon100) (with a molecular weight of about 4,500) (23 parts by weight) and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (60 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 100° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XVI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XVI) were measured at 10 GHz, and the results are shown in Table 5.

Example 32 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (III) of Example 3, obtaining Film (XVII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XVII) were measured at 10 GHz, and the results are shown in Table 5.

Example 33 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (IV) of Example 4, obtaining Film (XVIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XVIII) were measured at 10 GHz, and the results are shown in Table 5.

Example 34 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (V) of Example 5, obtaining Film (XIX). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XIX) were measured at 10 GHz, and the results are shown in Table 5.

Example 35 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (VI) of Example 6, obtaining Film (XX). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XX) were measured at 10 GHz, and the results are shown in Table 5.

Example 36 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (VIII) of Example 8, obtaining Film (XXI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXI) were measured at 10 GHz, and the results are shown in Table 5.

Example 37 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (IX) of Example 9, obtaining Film (XXII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXII) were measured at 10 GHz, and the results are shown in Table 5.

Example 38 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (XII) of Example 10, obtaining Film (XXIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXIII) were measured at 10 GHz, and the results are shown in Table 5.

Example 39 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (XIII) of Example 11, obtaining Film (XXIV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXIV) were measured at 10 GHz, and the results are shown in Table 5.

Example 40 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (XIV) of Example 12, obtaining Film (XXV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXV) were measured at 10 GHz, and the results are shown in Table 5.

Example 41 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (XV) of Example 13, obtaining Film (XXVI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXVI) were measured at 10 GHz, and the results are shown in Table 5.

Example 42 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVI) of Example 14, obtaining Film (XXVII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXVII) were measured at 10 GHz, and the results are shown in Table 5.

Example 43 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVII) of Example 15, obtaining Film (XXVIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXVIII) were measured at 10 GHz, and the results are shown in Table 5.

Example 44 was performed in the same manner as Example 31 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVIII) of Example 16, obtaining Film (XXIX). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXIX) were measured at 10 GHz, and the results are shown in Table 5.

Comparative Example 4

1,3,5-tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (TAIC) (31 parts by weight), polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000 (with a molecular weight of about 2,300) (46 parts by weight), polystyrene-butadiene-styrene (SBS, manufactured by Cray Valley with a trade No. of Ricon100) (with a molecular weight of about 4,500) (23 parts by weight) and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (50 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 100° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XXX). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXX) were measured at 10 GHz, and the results are shown in Table 5.

Copolymer (III) (10 parts by weight) of Example 3, polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000) (with a molecular weight of about 2,300) (90 parts by weight) and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (60 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 100° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XXXI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXXI) were measured at 10 GHz, and the results are shown in Table 6.

Example 46 was performed in the same manner as Example 45 except that the weight of Copolymer (III) was increased from 10 parts by weight to 20 parts by weight and the weight of polyphenylene ether was reduced from 90 parts by weight to 80 parts by weight, obtaining Film (XXXII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXXII) were measured at 10 GHz, and the results are shown in Table 6.

Example 47 was performed in the same manner as Example 45 except that the weight of Copolymer (III) was increased from 10 parts by weight to 80 parts by weight and the weight of polyphenylene ether was reduced from 90 parts by weight to 20 parts by weight, obtaining Film (XXXIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXXIII) were measured at 10 GHz, and the results are shown in Table 6.

Copolymer (I) (70 parts by weight) of Example 1, polystyrene-butadiene-styrene (SBS, manufactured by Cray Valley with a trade No. of Ricon100) (with a molecular weight of about 4,500) (30 parts by weight) and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (60 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 90° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XXXIV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXXIV) were measured at 10 GHz, and the results are shown in Table 6.

Example 49 was performed in the same manner as Example 48 except that Copolymer (I) of Example 1 was replaced with Copolymer (VIII) of Example 8, obtaining Film (XXXV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXXV) were measured at 10 GHz, and the results are shown in Table 6.

Example 50 was performed in the same manner as Example 45 except that polyphenylene ether was replaced with polystyrene-butadiene-styrene (SBS, manufactured by Cray Valley with a trade No. of Ricon100) (with a molecular weight of about 4,500), obtaining Film (XXXVI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXXVI) were measured at 10 GHz, and the results are shown in Table 6.

Example 51 was performed in the same manner as Example 50 except that the weight of Copolymer (III) was increased from 10 parts by weight to 20 parts by weight and the weight of polystyrene-butadiene-styrene was reduced from 90 parts by weight to 80 parts by weight, obtaining Film (XXXVII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXXVII) were measured at 10 GHz, and the results are shown in Table 6.

Example 52 was performed in the same manner as Example 50 except that the weight of Copolymer (III) was increased from 10 parts by weight to 50 parts by weight and the weight of polystyrene-butadiene-styrene was reduced from 90 parts by weight to 50 parts by weight, obtaining Film (XXXVIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXXVIII) were measured at 10 GHz, and the results are shown in Table 6.

Example 53 was performed in the same manner as Example 50 except that the weight of Copolymer (III) was increased from 10 parts by weight to 80 parts by weight and the weight of polystyrene-butadiene-styrene was reduced from 90 parts by weight to 20 parts by weight, obtaining Film (XXXIX). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXXIX) were measured at 10 GHz, and the results are shown in Table 6.

Example 54 was performed in the same manner as Example 45 except that polyphenylene ether was replaced with polybutadiene (PB, manufactured by Nippon Soda with a trade No. of B2000) (with a molecular weight of about 2,100), obtaining Film (XL). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XL) were measured at 10 GHz, and the results are shown in Table 6.

Example 55 was performed in the same manner as Example 54 except that the weight of Copolymer (III) was increased from 10 parts by weight to 20 parts by weight and the weight of polybutadiene was reduced from 90 parts by weight to 80 parts by weight, obtaining Film (XLI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XLI) were measured at 10 GHz, and the results are shown in Table 6.

Example 56 was performed in the same manner as Example 45 except that polyphenylene ether was replaced with polystyrene (PS, manufactured by Sigma-Aldrich) (with a molecular weight of about 192,000), obtaining Film (XLII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XLII) were measured at 10 GHz, and the results are shown in Table 6.

Copolymer (III) (70 parts by weight) of Example 3, epoxy resin (manufactured by Epolab Chemical Industries Inc. with a trade No. of ERL-4221) (30 parts by weight) and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (50 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 90° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XLIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XLIII) were measured at 10 GHz, and the results are shown in Table 6.

Copolymer (III) (31 parts by weight) of Example 3, polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000) (with a molecular weight of about 2,300) (46 parts by weight), polybutadiene (PB, manufactured by Nippon Soda with a trade No. of B2000) (with a molecular weight of about 2,100) (23 parts by weight) and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (60 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 100° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XLIV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XLIV) were measured at 10 GHz, and the results are shown in Table 6.

Copolymer (V) (38 parts by weight) of Example 5, polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000) (with a molecular weight of about 2,300) (57 parts by weight), bismaleimide (manufactured and sold by DAIWA KASEI CO., LTD) (5 parts by weight) and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (60 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 90° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XLV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XLV) were measured at 10 GHz, and the results are shown in Table 6.

Copolymer (III) (38 parts by weight) of Example 3, polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000) (with a molecular weight of about 2,300) (57 parts by weight), polystyrene (PS, manufactured by Sigma-Aldrich) (with a molecular weight of about 192,000) (5 parts by weight) and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (60 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 100° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XLVI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XLVI) were measured at 10 GHz, and the results are shown in Table 6.

Example 61 was performed in the same manner as Example 60 except that polystyrene was replaced with cyanate ester resin (CE, manufactured and sold by Eumate International Corp. with a trade No. of BADCy), obtaining Film (XLVII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XLVII) were measured at 10 GHz, and the results are shown in Table 6.

Example 62 was performed in the same manner as Example 60 except that polystyrene was replaced with polyimide (PI), obtaining Film (XLVIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XLVIII) were measured at 10 GHz, and the results are shown in Table 6.

Comparative Example 5

Comparative Example 5 was performed in the same manner as Example 45 except that the weight of Copolymer (III) was reduced from 10 parts by weight to 1 part by weight and the weight of polyphenylene ether was increased from 90 parts by weight to 99 parts by weight, obtaining Film (XLIX). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XLIX) were measured at 10 GHz, and the results are shown in Table 6.

Comparative Example 6

Comparative Example 6 was performed in the same manner as Example 45 except that the weight of Copolymer (III) was increased from 10 parts by weight to 90 parts by weight and the weight of polyphenylene ether was reduced from 90 parts by weight to 10 parts by weight, obtaining Film (L). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (L) were measured at 10 GHz, and the results are shown in Table 6.

Comparative Example 7

Comparative Example 7 was performed in the same manner as Example 57 except that the weight of Copolymer (III) was reduced from 70 parts by weight to 50 parts by weight and the weight of epoxy resin was reduced from 30 parts by weight to 50 parts by weight, obtaining Film (LI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (LI) were measured at 10 GHz, and the results are shown in Table 6.

Comparative Example 8

Phenolic novolac curing agent (manufactured and sold by Momentive with a trade No. of SD1708) (45 parts by weight), epoxy resin (manufactured by Epolab Chemical Industries Inc. with a trade No. of ERL-4221) (55 parts by weight) and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene (50 parts by weight). After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 100° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (LII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (LII) were measured at 10 GHz, and the results are shown in Table 6.

Comparative Example 9

Copolymer (III) (1 parts by weight) of Example 3, polyimide (PI) (99 parts by weight), and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene. After mixing completely, a resin composition was obtained. Next, the aforementioned resin composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the resin composition was heated at 100° C. for a period of time. Next, the above copper foil was then heated gradually and then the resin composition was subjected to a crosslinking reaction under a temperature lower than 250° C. (in order to achieve the best crosslinking density), obtaining Film (LIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (LIII) were measured at 10 GHz, and the results are shown in Table 6.

Copolymer (III) (17 parts by weight) of Example 3, polyphenylene ether (PPE, manufactured and sold by Mitsubishi Gas Chemical with a trade No. of OPE-2st (with a molecular weight of about 2,200) (70 parts by weight), polystyrene-butadiene-styrene (SBS, manufactured and sold by Cray Valley. with a trade No. of Ricon100) (with a molecular weight of about 4,500) (13 parts by weight) and an initiator (1 part by weight) were added into a reaction bottle, and then dissolved in toluene. After mixing completely, a composition was obtained. After stirring completely, a composition was obtained. Next, glass fiber (sold by Asahi Fiber Glass with a trade No. of L2116) was immersed in the aforementioned composition, wherein the impregnated amount was about 59%. After removing the glass fiber from the resin composition, the glass fiber was baked at 140° C. in a hot air circulating oven to keep the crosslinking degree to about 50%, obtaining a prepreg. Four prepregs were stacked, and a copper foil, a mirror plate, and a Kraft paper were disposed on the top surface and the bottom surface of the stacked structure. The obtained structure was heated to 210° C. gradually by a vacuum molding machine for 3 hr, obtaining Copper foil substrate (I) with a thickness of 0.558 mm. Next, the dielectric constant (Dk) and the dissipation factor (Df) of Copper foil substrate (I) were measured at 10 GHz, and the results are shown in Table 7.

As shown in Tables 4-7, since the resin composition includes an oligomer having a structure represented by Formula (I), the cured product exhibits a relatively low dielectric constant (less than or equal to 3.0 (at 10 GHz) and a relatively low dissipation factor (less than or equal to 0.0045 (at 10 GHz)), thereby serving as a good material for a high-frequency substrate. As shown in the above Examples, the resin composition of the disclosure can be crosslinked at a temperature lower than 250° C., and the obtained oligomer exhibits superior crosslinking density. Furthermore, the oligomer can achieve optimal crosslinking density which is checked by means of the crosslinking exotherm determined by differential scanning calorimetry.

It will be clear that various modifications and variations can be made to the disclosed methods and materials. It is intended that the specification and examples be considered as exemplary only, with the true scope of the disclosure being indicated by the following claims and their equivalents.