CN109791992A - 高聚物、包含其的混合物、组合物和有机电子器件以及用于聚合的单体 - Google Patents
高聚物、包含其的混合物、组合物和有机电子器件以及用于聚合的单体 Download PDFInfo
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- CN109791992A CN109791992A CN201780059565.9A CN201780059565A CN109791992A CN 109791992 A CN109791992 A CN 109791992A CN 201780059565 A CN201780059565 A CN 201780059565A CN 109791992 A CN109791992 A CN 109791992A
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
本申请公开一种高聚物、包含其的混合物、组合物和有机电子器件以及聚合单体,其中,所述高聚物包括重复单元E1和重复单元E2,所述重复单元E1侧链上的E1基团和所述重复单元E2侧链上的E2基团具有形成激基络合物(Exciplex)特性,即其中min((LUMO(E1)‑HOMO(E2),LUMO(E2)‑HOMO(E1))≤min(ET(E1),ET(E2))+0.1eV,从而提供了一种适合于印刷工艺的高聚物,进而降低OLED制造成本。
Description
PCT国内申请,说明书已公开。
Claims (20)
- PCT国内申请,权利要求书已公开。
Applications Claiming Priority (3)
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CN201611047040 | 2016-11-23 | ||
CN2016110470407 | 2016-11-23 | ||
PCT/CN2017/112716 WO2018095395A1 (zh) | 2016-11-23 | 2017-11-23 | 高聚物、包含其的混合物、组合物和有机电子器件以及用于聚合的单体 |
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CN109791992A true CN109791992A (zh) | 2019-05-21 |
CN109791992B CN109791992B (zh) | 2021-07-23 |
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US (1) | US11453745B2 (zh) |
EP (1) | EP3547384B1 (zh) |
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US11404644B2 (en) * | 2016-12-22 | 2022-08-02 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organic functional compounds, mixtures, formulations, organic functional thin films and preparation methods therefor and organic electronic devices |
US11482679B2 (en) * | 2017-05-23 | 2022-10-25 | Kyushu University, National University Corporation | Compound, light-emitting lifetime lengthening agent, use of n-type compound, film and light-emitting device |
KR20200068503A (ko) * | 2018-12-05 | 2020-06-15 | 엘지디스플레이 주식회사 | 유기발광다이오드 및 이를 포함하는 유기발광장치 |
CN114616233B (zh) | 2019-12-30 | 2024-09-03 | 广州华睿光电材料有限公司 | 有机电致发光器件和含稠环的芳香族化合物 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1379009A (zh) * | 2001-03-30 | 2002-11-13 | 捷时雅股份有限公司 | 包含吸电子基团和供电子基团的单体、以及包含它的共聚物和质子导电膜 |
WO2007119420A1 (ja) * | 2006-03-22 | 2007-10-25 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の発光色度安定化方法、照明装置及び電子ディスプレイ装置 |
WO2009116414A1 (ja) * | 2008-03-19 | 2009-09-24 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
US20100045171A1 (en) * | 2006-09-08 | 2010-02-25 | Konica Minolta Holdings, Inc. | Organic electroluminescence element, lighting device and display device |
US20100171101A1 (en) * | 2006-03-30 | 2010-07-08 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, method of manufacturing organic electroluminescent element, lighting device, and display device |
US20110084601A1 (en) * | 2008-07-01 | 2011-04-14 | Konica Minolta Holdings, Inc. | White light emission organic electroluminescent element, illuminating device and display |
WO2016086886A1 (zh) * | 2014-12-04 | 2016-06-09 | 广州华睿光电材料有限公司 | 聚合物,包含其的混合物、组合物、有机电子器件,及其单体 |
Family Cites Families (79)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3567450A (en) | 1968-02-20 | 1971-03-02 | Eastman Kodak Co | Photoconductive elements containing substituted triarylamine photoconductors |
US3615404A (en) | 1968-04-25 | 1971-10-26 | Scott Paper Co | 1 3-phenylenediamine containing photoconductive materials |
US4720432A (en) | 1987-02-11 | 1988-01-19 | Eastman Kodak Company | Electroluminescent device with organic luminescent medium |
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
US5121029A (en) | 1987-12-11 | 1992-06-09 | Idemitsu Kosan Co., Ltd. | Electroluminescence device having an organic electroluminescent element |
US5130603A (en) | 1989-03-20 | 1992-07-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
JP2913116B2 (ja) | 1990-11-20 | 1999-06-28 | 株式会社リコー | 電界発光素子 |
JP2686418B2 (ja) | 1994-08-12 | 1997-12-08 | 東洋インキ製造株式会社 | ジアリールアミン誘導体、その製造方法及び用途 |
DE69625018T2 (de) | 1995-09-25 | 2003-04-10 | Toyo Ink Mfg Co | Leuchtemittierender Stoff für organische Elektrolumineszensvorrichtung, und organische Elektrolumineszensvorrichtung mit diesem leuchtemittierendem dafür geeignetem Stoff |
GB9826406D0 (en) | 1998-12-02 | 1999-01-27 | South Bank Univ Entpr Ltd | Quinolates |
US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
US6020078A (en) | 1998-12-18 | 2000-02-01 | Eastman Kodak Company | Green organic electroluminescent devices |
CN100407448C (zh) | 1999-05-13 | 2008-07-30 | 普林斯顿大学理事会 | 基于电致磷光的极高效有机发光器件 |
KR100738762B1 (ko) | 1999-09-21 | 2007-07-12 | 이데미쓰 고산 가부시키가이샤 | 유기 전자발광 소자 및 유기 발광 매체 |
DE60045110D1 (de) | 1999-12-01 | 2010-11-25 | Univ Princeton | Erungsmittel in organischen led's |
JP4048521B2 (ja) | 2000-05-02 | 2008-02-20 | 富士フイルム株式会社 | 発光素子 |
US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
WO2002015645A1 (en) | 2000-08-11 | 2002-02-21 | The Trustees Of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorescence |
JP4154140B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物 |
JP4154139B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子 |
JP4154138B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子、表示装置及び金属配位化合物 |
CN1271041C (zh) | 2001-03-16 | 2006-08-23 | 出光兴产株式会社 | 芳香氨基化合物的生产方法 |
US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
DE10345572A1 (de) | 2003-09-29 | 2005-05-19 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
US7029766B2 (en) | 2003-12-05 | 2006-04-18 | Eastman Kodak Company | Organic element for electroluminescent devices |
US6824895B1 (en) | 2003-12-05 | 2004-11-30 | Eastman Kodak Company | Electroluminescent device containing organometallic compound with tridentate ligand |
US7598388B2 (en) | 2004-05-18 | 2009-10-06 | The University Of Southern California | Carbene containing metal complexes as OLEDs |
CN100368363C (zh) | 2004-06-04 | 2008-02-13 | 友达光电股份有限公司 | 蒽化合物以及包括此蒽化合物的有机电致发光装置 |
DE102004031000A1 (de) | 2004-06-26 | 2006-01-12 | Covion Organic Semiconductors Gmbh | Organische Elektrolumineszenzvorrichtungen |
TW200613515A (en) | 2004-06-26 | 2006-05-01 | Merck Patent Gmbh | Compounds for organic electronic devices |
DE102004034517A1 (de) | 2004-07-16 | 2006-02-16 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
TW200639140A (en) | 2004-12-01 | 2006-11-16 | Merck Patent Gmbh | Compounds for organic electronic devices |
JP4263700B2 (ja) | 2005-03-15 | 2009-05-13 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
US20060222886A1 (en) | 2005-04-04 | 2006-10-05 | Raymond Kwong | Arylpyrene compounds |
DE102005023437A1 (de) | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
US7588839B2 (en) | 2005-10-19 | 2009-09-15 | Eastman Kodak Company | Electroluminescent device |
US20070092759A1 (en) | 2005-10-26 | 2007-04-26 | Begley William J | Organic element for low voltage electroluminescent devices |
US7767317B2 (en) | 2005-10-26 | 2010-08-03 | Global Oled Technology Llc | Organic element for low voltage electroluminescent devices |
US20070092753A1 (en) | 2005-10-26 | 2007-04-26 | Eastman Kodak Company | Organic element for low voltage electroluminescent devices |
DE102005058557A1 (de) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102005058543A1 (de) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
KR20160030582A (ko) | 2006-02-10 | 2016-03-18 | 유니버셜 디스플레이 코포레이션 | 시클로금속화 이미다조[1,2-f]페난트리딘 및 디이미다조[1,2-a:1'',2''-c]퀴나졸린 리간드, 및 이의 등전자성 및 벤즈고리화된 유사체의 금속 착체 |
DE102006015183A1 (de) | 2006-04-01 | 2007-10-04 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US20070252517A1 (en) | 2006-04-27 | 2007-11-01 | Eastman Kodak Company | Electroluminescent device including an anthracene derivative |
DE102006025846A1 (de) | 2006-06-02 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006031990A1 (de) | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
JP2008124156A (ja) | 2006-11-09 | 2008-05-29 | Idemitsu Kosan Co Ltd | 有機el材料含有溶液、有機el材料の薄膜形成方法、有機el材料の薄膜、有機el素子 |
US7645142B2 (en) | 2007-09-05 | 2010-01-12 | Vivant Medical, Inc. | Electrical receptacle assembly |
US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
DE102008015526B4 (de) | 2008-03-25 | 2021-11-11 | Merck Patent Gmbh | Metallkomplexe |
DE102008027005A1 (de) | 2008-06-05 | 2009-12-10 | Merck Patent Gmbh | Organische elektronische Vorrichtung enthaltend Metallkomplexe |
DE102008036247A1 (de) | 2008-08-04 | 2010-02-11 | Merck Patent Gmbh | Elektronische Vorrichtungen enthaltend Metallkomplexe |
DE102008048336A1 (de) | 2008-09-22 | 2010-03-25 | Merck Patent Gmbh | Einkernige neutrale Kupfer(I)-Komplexe und deren Verwendung zur Herstellung von optoelektronischen Bauelementen |
DE102008057050B4 (de) | 2008-11-13 | 2021-06-02 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008057051B4 (de) | 2008-11-13 | 2021-06-17 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009007038A1 (de) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metallkomplexe |
DE102009011223A1 (de) | 2009-03-02 | 2010-09-23 | Merck Patent Gmbh | Metallkomplexe |
DE102009013041A1 (de) | 2009-03-13 | 2010-09-16 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US8586203B2 (en) | 2009-05-20 | 2013-11-19 | Universal Display Corporation | Metal complexes with boron-nitrogen heterocycle containing ligands |
JP6246468B2 (ja) | 2010-03-11 | 2017-12-13 | メルク パテント ゲーエムベーハー | 治療および化粧品におけるファイバー |
US20130059924A1 (en) | 2010-05-12 | 2013-03-07 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Photostabilisers |
JP6054290B2 (ja) | 2010-06-15 | 2016-12-27 | メルク パテント ゲーエムベーハー | 金属錯体 |
DE102010027316A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metallkomplexe |
DE102010027317A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metallkomplexe |
DE102010027319A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metallkomplexe |
US9783734B2 (en) | 2011-02-28 | 2017-10-10 | Kyulux, Inc. | Delayed fluorescence material and organic electroluminescence device |
EP2733762B1 (en) | 2011-07-15 | 2018-11-28 | Kyulux, Inc. | Organic electroluminescence element and compound used therein |
US10454038B2 (en) | 2011-07-15 | 2019-10-22 | Kyulux, Inc. | Delayed-fluorescence material and organic electroluminescence element using same |
CN102270751A (zh) * | 2011-07-26 | 2011-12-07 | 昆山维信诺显示技术有限公司 | 一种有机电致磷光发光器件及其制备方法 |
JP6095643B2 (ja) | 2012-03-09 | 2017-03-15 | 株式会社Kyulux | 発光材料および有機発光素子 |
JP2014135466A (ja) | 2012-04-09 | 2014-07-24 | Kyushu Univ | 有機発光素子ならびにそれに用いる発光材料および化合物 |
CN104271701A (zh) | 2012-04-25 | 2015-01-07 | 国立大学法人九州大学 | 发光材料和有机发光元件 |
JP5594750B2 (ja) | 2012-05-17 | 2014-09-24 | 国立大学法人九州大学 | 化合物、発光材料および有機発光素子 |
CN103483332B (zh) | 2013-09-11 | 2016-08-10 | 中山大学 | 具有热激活延迟荧光和聚集诱导发光性能的压致发光材料及其合成方法和应用 |
CN105679949A (zh) * | 2014-12-04 | 2016-06-15 | 广州华睿光电材料有限公司 | 有机发光晶体管及其应用 |
US10319912B2 (en) | 2015-01-29 | 2019-06-11 | Samsung Electronics Co., Ltd. | Charge-transporting material and organic light-emitting device including the same |
-
2017
- 2017-11-23 CN CN201780059565.9A patent/CN109791992B/zh active Active
- 2017-11-23 EP EP17874343.1A patent/EP3547384B1/en active Active
- 2017-11-23 US US16/463,273 patent/US11453745B2/en active Active
- 2017-11-23 WO PCT/CN2017/112716 patent/WO2018095395A1/zh unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1379009A (zh) * | 2001-03-30 | 2002-11-13 | 捷时雅股份有限公司 | 包含吸电子基团和供电子基团的单体、以及包含它的共聚物和质子导电膜 |
WO2007119420A1 (ja) * | 2006-03-22 | 2007-10-25 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の発光色度安定化方法、照明装置及び電子ディスプレイ装置 |
US20100171101A1 (en) * | 2006-03-30 | 2010-07-08 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, method of manufacturing organic electroluminescent element, lighting device, and display device |
US20100045171A1 (en) * | 2006-09-08 | 2010-02-25 | Konica Minolta Holdings, Inc. | Organic electroluminescence element, lighting device and display device |
WO2009116414A1 (ja) * | 2008-03-19 | 2009-09-24 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
US20110084601A1 (en) * | 2008-07-01 | 2011-04-14 | Konica Minolta Holdings, Inc. | White light emission organic electroluminescent element, illuminating device and display |
WO2016086886A1 (zh) * | 2014-12-04 | 2016-06-09 | 广州华睿光电材料有限公司 | 聚合物,包含其的混合物、组合物、有机电子器件,及其单体 |
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US11453745B2 (en) | 2022-09-27 |
CN109791992B (zh) | 2021-07-23 |
EP3547384A4 (en) | 2019-11-27 |
EP3547384A1 (en) | 2019-10-02 |
WO2018095395A1 (zh) | 2018-05-31 |
US20190292309A1 (en) | 2019-09-26 |
EP3547384B1 (en) | 2022-10-05 |
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