JP2019127440A - 共役ピリジル基を有するトリアジン化合物 - Google Patents
共役ピリジル基を有するトリアジン化合物 Download PDFInfo
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- JP2019127440A JP2019127440A JP2018007885A JP2018007885A JP2019127440A JP 2019127440 A JP2019127440 A JP 2019127440A JP 2018007885 A JP2018007885 A JP 2018007885A JP 2018007885 A JP2018007885 A JP 2018007885A JP 2019127440 A JP2019127440 A JP 2019127440A
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- Prior art keywords
- group
- triazine compound
- layer
- phenyl
- naphthyl
- Prior art date
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- -1 Triazine compound Chemical class 0.000 title claims abstract description 179
- 125000004076 pyridyl group Chemical group 0.000 title claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 17
- 125000006267 biphenyl group Chemical group 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 8
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
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- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 2
- 239000010410 layer Substances 0.000 description 134
- 238000002347 injection Methods 0.000 description 26
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- 238000000034 method Methods 0.000 description 25
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- 229910052757 nitrogen Inorganic materials 0.000 description 19
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- 239000000758 substrate Substances 0.000 description 12
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 3
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
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- FNMVYTWTGWHRAY-UHFFFAOYSA-N 2-(3-chloro-5-phenanthren-9-ylphenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C=1C(C=2C3=CC=CC=C3C3=CC=CC=C3C=2)=CC(Cl)=CC=1C(N=1)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 FNMVYTWTGWHRAY-UHFFFAOYSA-N 0.000 description 2
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
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- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
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Images
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- Electroluminescent Light Sources (AREA)
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Abstract
Description
Ar1は、同一の基を表し、フェニル基、ナフチル基、又はビフェニル基(これらの基は、フッ素原子、炭素数1〜4のアルコキシ基、炭素数1〜4のアルキル基、フェニル基、ナフチル基、キノリル基、又はピリジル基で置換されていてもよい。)を表す。
Ar2は、炭素数10〜18の縮環の芳香族炭化水素基を表す。
Ar3は、2つ以上の環で構成される総炭素数10〜24の芳香族炭化水素基、又は2つ以上の環で構成される総炭素数6〜23の含窒素芳香族基を表す。)
(i)陽極/発光層/陰極
(ii)陽極/正孔輸送層/発光層/陰極
(iii)陽極/発光層/電子輸送層/陰極
(iv)陽極/正孔輸送層/発光層/電子輸送層/陰極
(v)陽極/陽極バッファー層/正孔輸送層/発光層/電子輸送層/陰極バッファー層/陰極
本発明の有機電界発光素子における発光層には、従来公知の発光材料を用いることができる。発光層を形成する方法としては、例えば蒸着法、スピンコート法、キャスト法、LB法などの公知の方法により薄膜を形成する方法がある。
2.正孔注入層
3.電荷発生層
4.正孔輸送層
5.発光層
6.電子輸送層
7.陰極層
合成例−3
素子評価に用いた化合物の構造式及びその略称を以下に示す。
基板には、2mm幅の酸化インジウム−スズ(ITO)膜(膜厚110nm)がストライプ状にパターンされたITO透明電極付きガラス基板を用いた。この基板をイソプロピルアルコールで洗浄した後、オゾン紫外線洗浄にて表面処理を行った。洗浄後の基板に、真空蒸着法で各層の真空蒸着を行い、断面図を図1に示すような発光面積4mm2有機電界発光素子を作製した。なお、各有機材料は抵抗加熱方式により成膜した。
素子実施例−1において、電子輸送層6に、4,6−ジフェニル−2−{3−[6−(3−キノリル)ピリジン−3−イル]−5−(9−フェナントリル)フェニル}−1,3,5−トリアジン(化合物 A−5)を30nm成膜(成膜速度0.15nm/秒)する代わりに、化合物 ETL−1を30nm成膜(成膜速度0.15nm/秒)した以外は、素子実施例−1と同じ方法で有機電界発光素子を作成した。
Claims (7)
- Ar1が、同一の基を表し、無置換のフェニル基、無置換のナフチル基、又は無置換のビフェニリル基である請求項1に記載のトリアジン化合物。
- Ar1が、同一の基を表し、無置換のフェニル基である請求項1又は請求項2に記載のトリアジン化合物。
- Ar2が、ナフチル基、アントリル基、フェナントリル基、ピレキニル基、トリフェニレニル基、フルオランテニル基、クリセニル基、フルオレニル基、又はベンゾフルオレニル基である請求項1乃至3に記載のトリアジン化合物。
- Ar3が、ビフェニル基、テルフェニル基、ナフチル基、アントリル基、フェナントリル基、ピレニル基、トリフェニレニル基、フルオランテニル基、クリセニル基、ビピリジル基、アザナフチル基、ジアザナフチル基、トリアザナフチル基、テトラアザナフチル基、アザアントリル基、ジアザアントリル基、アザフェナントリル基、ジアザフェナントリル基、フェニル置換ピリジル基、ピリジル置換フェニル基、ビフェニル置換ピリジル基、又はピリジル置換ビフェニル基である請求項1乃至4に記載のトリアジン化合物。
- 請求項1に記載のトリアジン化合物を含有することを特徴とする、有機電界発光素子用材料。
- 請求項1に記載のトリアジン化合物を含有することを特徴とする、有機電界発光素子用電子輸送材料。
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