JP2019182843A - 有機電界発光素子及び有機電界発光素子用多環化合物 - Google Patents
有機電界発光素子及び有機電界発光素子用多環化合物 Download PDFInfo
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
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- 238000007738 vacuum evaporation Methods 0.000 description 1
- TYHJXGDMRRJCRY-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) tin(4+) Chemical compound [O-2].[Zn+2].[Sn+4].[In+3] TYHJXGDMRRJCRY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
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Abstract
Description
本発明の一実施形態による多環化合物は、例えば、下記のように合成することができる。但し、本発明の一実施形態による多環化合物の合成方法は、これに限定されない。
本発明の一実施形態による化合物8は、例えば、以下のように合成することができる。
本発明の一実施形態による化合物40は、例えば、以下のように合成することができる。
本発明の一実施形態による化合物69は、例えば、以下のように合成することができる。
本発明の一実施形態による化合物127は、例えば、以下のように合成することができる。
本発明の一実施形態による化合物131は、例えば、以下のように合成することができる。
上述した化合物8、40、69、127、及び131を発光層のドーパント材料として使用し、実施例1〜5の有機電界発光素子を作製した。
EL1 第1電極
HTR 正孔輸送領域
HIL 正孔注入層
HTL 正孔輸送層
EML 発光層
ETR 電子輸送領域
ETL 電子輸送層
EIL 電子注入層
EL2 第2電極
Claims (10)
- 下記化学式1で表される多環化合物。
X1は、C、SiまたはGeであり、
Arは、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
R1〜R4は、それぞれ独立して重水素原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
a〜dは、それぞれ独立して0以上4以下の整数であり、
ACは下記化学式2〜10の何れか1つで表され、
Z1〜Z13はそれぞれ独立してCHまたはNであり、Z1〜Z3のうち2つまたは3つはNであり、Z4〜Z13のうち少なくとも1つはNであり、
eは0以上2以下の整数であり、
前記化学式3において、
X2はO、SまたはCR8R9であり、
R5〜R7は、それぞれ独立して重水素原子、または置換若しくは無置換の炭素数1以上5以下のアルキル基であり、隣接する基と互いに結合して炭化水素環またはヘテロ環を形成するか又は形成せず、
R8、R9は、それぞれ独立して水素原子、重水素原子、または置換若しくは無置換の炭素数1以上5以下のアルキル基であり、隣接する基と互いに結合して炭化水素環またはヘテロ環を形成するか又は形成せず、
fは0以上3以下の整数であり、
gは0以上4以下の整数であり、
hは0以上5以下の整数であり、
前記化学式4において、
iは0〜2の整数であり、
Y1はNまたはCR10であり、Y2はNまたはCR11であり、Y3はNまたはCR12であり、Y4はNまたはCR13であり、Y5はNまたはCR14であり、Y1〜Y5のうち少なくとも1つはNであり、
R10〜R14は、それぞれ独立して水素原子、重水素原子、シアノ基、置換若しくは無置換の炭素数1以上10以下のアルキル基、またはトリフルオロメチル基であり、
化学式1のX1がCである場合には、R10からR14のうち少なくとも1つは、水素原子ではなく、
Y2及びY4のうち少なくとも1つがNである場合、Y3はCR12であり、R12はシアノ基ではなく、
前記化学式7において、
A1〜A13は、それぞれ独立してNまたはCR15であり、
A1〜A8のうち少なくとも1つはNであり、A9〜A13のうち少なくとも1つはNであり、
A1〜A13のうち1つは化学式1のNと結合される部位であり、
R15は、水素原子、重水素原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
前記化学式8において、
B1〜B10は、それぞれ独立してNまたはCR16であり、
B1〜B10のうち1つは、化学式1のNと結合される部位であり、
X3は単結合、O、S、CR17R18、またはSiR19R20であり、
jは0または1であり、jが1である場合、B5及びB6はCであり、
R16〜R20は、それぞれ独立して水素原子、重水素原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基であり、
前記化学式9において、
E1〜E10は、それぞれ独立してNまたはCR21であり、
E1〜E10のうち1つは、化学式1のNと結合される部位であり、
X3は単結合、O、S、CR22R23、またはSiR24R25であり、
kは0または1であり、kが1である場合、E5及びE6はCであり、
R21〜R25は、それぞれ独立して水素原子、重水素原子、置換若しくは無置換の炭素数1以上10以下のアルキル基、置換若しくは無置換の環形成炭素数6以上30以下のアリール基、または置換若しくは無置換の環形成炭素数2以上30以下のヘテロアリール基である。) - 前記化学式3は、下記化学式3−1または3−2で表されることを特徴とする請求項1に記載の多環化合物。
Y1及びY2は、それぞれ独立してO、SまたはCR26R27であり、
R26及びR27は、それぞれ独立して水素原子、重水素原子、置換若しくは無置換の炭素数1以上5以下のアルキル基である。) - 前記化学式4は、下記化学式の何れか1つで表されることを特徴とする請求項1に記載の多環化合物。
- 前記化学式7は、下記化学式の何れか1つで表されることを特徴とする請求項1に記載の多環化合物。
- 前記化学式8は、下記化学式の何れか1つで表されることを特徴とする請求項1に記載の多環化合物。
- 化学式9は、下記化学式の何れか1つで表されることを特徴とする請求項1に記載の多環化合物。
- 前記化学式1で表される多環化合物は、下記化合物群1に表された化合物から選択される何れか1つであることを特徴とする請求項1に記載の多環化合物。
[化合物群1]
- 第1電極と、
前記第1電極上に設けられた正孔輸送領域と、
前記正孔輸送領域上に設けられ、請求項1〜請求項7の何れか1つの多環化合物を含む発光層と、
前記発光層上に設けられた電子輸送領域と、
前記電子輸送領域上に設けられた第2電極と、を含むことを特徴とする有機電界発光素子。 - 前記発光層は、ホスト及びドーパントを含み、
前記ドーパントが前記多環化合物を含むことを特徴とする請求項8に記載の有機電界発光素子。 - 前記多環化合物は、470nm未満の波長領域を有する青色ドーパントであることを特徴とする請求項9に記載の有機電界発光素子。
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KR102648402B1 (ko) * | 2018-06-12 | 2024-03-18 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
US20210159424A1 (en) * | 2019-11-26 | 2021-05-27 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Hole transporting material using spirobiacridine as core and organic light emitting diode |
CN110950866B (zh) * | 2019-11-26 | 2023-06-27 | 武汉华星光电半导体显示技术有限公司 | 以螺双吖啶为核的空穴传输材料及有机发光二极管 |
CN112812115B (zh) * | 2020-02-28 | 2022-03-29 | 广东聚华印刷显示技术有限公司 | 吖啶类化合物、聚合物及其应用、发光器件 |
CN111378438B (zh) * | 2020-03-18 | 2021-09-21 | 中国科学院长春应用化学研究所 | 含有芳基硼受体和空间电荷转移发光的荧光高分子化合物、制备方法及有机电致发光器件 |
US20220098220A1 (en) * | 2020-09-29 | 2022-03-31 | Universal Dispaly Corporation | Organic electroluminescent materials and devices |
CN113620973B (zh) * | 2021-07-16 | 2024-05-07 | 西北工业大学 | 一种热活化延迟荧光材料及其制备方法和应用 |
CN113816960A (zh) * | 2021-09-28 | 2021-12-21 | 浙江华显光电科技有限公司 | 有机化合物及包括该化合物的有机电致发光器件 |
CN117964635B (zh) * | 2024-04-02 | 2024-07-05 | 大连理工大学 | 一种基于螺式硫杂蒽的有机发光材料及其制备方法和应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20110110508A (ko) * | 2010-04-01 | 2011-10-07 | 에스에프씨 주식회사 | 스피로 화합물 및 이를 포함하는 유기전계발광소자 |
KR20110120075A (ko) * | 2010-04-28 | 2011-11-03 | 에스에프씨 주식회사 | 스피로 화합물 및 이를 포함하는 유기전계발광소자 |
JP2017513855A (ja) * | 2014-04-14 | 2017-06-01 | メルク パテント ゲーエムベーハー | 電子素子のための材料 |
CN106831773A (zh) * | 2017-01-05 | 2017-06-13 | 华南理工大学 | 含9,9’‑螺吖啶的化合物及其制备方法和应用 |
CN109438446A (zh) * | 2018-12-28 | 2019-03-08 | 上海天马有机发光显示技术有限公司 | 一种电致发光化合物、oled显示面板及电子设备 |
KR20190037176A (ko) * | 2017-09-28 | 2019-04-05 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8586210B2 (en) * | 2008-09-24 | 2013-11-19 | Hodogaya Chemical Co., Ltd. | Compound having substituted anthracene ring structure and pyridoindole ring structure and organic electroluminescence device |
KR101929860B1 (ko) * | 2015-05-15 | 2018-12-17 | 삼성에스디아이 주식회사 | 유기광전자소자 및 표시장치 |
-
2018
- 2018-04-05 KR KR1020180039925A patent/KR20190117038A/ko active IP Right Grant
-
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- 2019-03-19 EP EP21203301.3A patent/EP3978495B1/en active Active
- 2019-03-26 JP JP2019059048A patent/JP2019182843A/ja active Pending
-
2023
- 2023-10-13 JP JP2023177566A patent/JP2024020205A/ja active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20110110508A (ko) * | 2010-04-01 | 2011-10-07 | 에스에프씨 주식회사 | 스피로 화합물 및 이를 포함하는 유기전계발광소자 |
KR20110120075A (ko) * | 2010-04-28 | 2011-11-03 | 에스에프씨 주식회사 | 스피로 화합물 및 이를 포함하는 유기전계발광소자 |
JP2017513855A (ja) * | 2014-04-14 | 2017-06-01 | メルク パテント ゲーエムベーハー | 電子素子のための材料 |
CN106831773A (zh) * | 2017-01-05 | 2017-06-13 | 华南理工大学 | 含9,9’‑螺吖啶的化合物及其制备方法和应用 |
KR20190037176A (ko) * | 2017-09-28 | 2019-04-05 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
CN109438446A (zh) * | 2018-12-28 | 2019-03-08 | 上海天马有机发光显示技术有限公司 | 一种电致发光化合物、oled显示面板及电子设备 |
Non-Patent Citations (2)
Title |
---|
CHEMISTRY OF MATERIALS, vol. 29(20), JPN6022054329, 2017, pages 8630 - 8636, ISSN: 0005108040 * |
JOURNAL OF MATERIALS CHEMISTRY C, vol. 2, JPN6022054328, 2014, pages 9565 - 9578, ISSN: 0005108041 * |
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EP3549941A2 (en) | 2019-10-09 |
CN110343105A (zh) | 2019-10-18 |
EP3549941B1 (en) | 2021-10-20 |
EP3978495B1 (en) | 2023-05-10 |
US20190312210A1 (en) | 2019-10-10 |
KR20190117038A (ko) | 2019-10-16 |
EP3549941A3 (en) | 2019-11-20 |
CN110343105B (zh) | 2023-10-24 |
JP2024020205A (ja) | 2024-02-14 |
CN117327071A (zh) | 2024-01-02 |
EP3978495A1 (en) | 2022-04-06 |
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