CN102498186A - 发磷光的金属配合物、用于制造其的方法和发射辐射的器件 - Google Patents
发磷光的金属配合物、用于制造其的方法和发射辐射的器件 Download PDFInfo
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- CN102498186A CN102498186A CN2010800394376A CN201080039437A CN102498186A CN 102498186 A CN102498186 A CN 102498186A CN 2010800394376 A CN2010800394376 A CN 2010800394376A CN 201080039437 A CN201080039437 A CN 201080039437A CN 102498186 A CN102498186 A CN 102498186A
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- binding substances
- condensation
- alkyl
- aromatics
- heterocycle
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- 125000000217 alkyl group Chemical group 0.000 claims description 27
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- 238000009833 condensation Methods 0.000 claims description 20
- 230000005494 condensation Effects 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
Claims (17)
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DE102009031683A DE102009031683A1 (de) | 2009-07-03 | 2009-07-03 | Phophoreszente Metallkomplexverbindung, Verfahren zur Herstellung dazu und strahlungsemittierendes Bauelement |
DE102009031683.3 | 2009-07-03 | ||
PCT/EP2010/056111 WO2011000616A1 (de) | 2009-07-03 | 2010-05-05 | Phosphoreszente metallkomplexverbindung, verfahren zur herstellung dazu und strahlungsemittierendes bauelement |
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CN102498186A true CN102498186A (zh) | 2012-06-13 |
CN102498186B CN102498186B (zh) | 2014-12-03 |
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US (1) | US20120169213A1 (zh) |
EP (1) | EP2718394B1 (zh) |
JP (1) | JP5705218B2 (zh) |
KR (1) | KR101441402B1 (zh) |
CN (1) | CN102498186B (zh) |
DE (1) | DE102009031683A1 (zh) |
WO (1) | WO2011000616A1 (zh) |
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Publication number | Priority date | Publication date | Assignee | Title |
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DE102010005634A1 (de) | 2010-01-25 | 2011-07-28 | Siemens Aktiengesellschaft, 80333 | Neuartige Verwendung des Guanidinium-Kations und lichtemittierendes Bauelement |
DE102010005632A1 (de) | 2010-01-25 | 2011-07-28 | Siemens Aktiengesellschaft, 80333 | Phosphoreszente Metallkomplexverbindung, Verfahren zur Herstellung und lichtemittierendes Bauelement |
DE102010023959B4 (de) | 2010-06-16 | 2013-02-21 | Osram Ag | Neue Verbindungen als Liganden für Übergangsmetallkomplexe und daraus hergestellte Materialien, sowie Verwendung dazu |
WO2012023992A1 (en) | 2010-08-20 | 2012-02-23 | Rhodia Operations | Films containing electrically conductive polymers |
DE102011006360A1 (de) | 2011-03-29 | 2012-10-04 | Siemens Aktiengesellschaft | Komplexierung niedermolekularer Halbleiter für die Anwendung als Emitterkomplex in organischen lichtemitterenden elektrochemischen Zellen (OLEECs) |
DE102011017572A1 (de) | 2011-04-27 | 2012-10-31 | Siemens Aktiengesellschaft | Bauteil mit orientiertem organischem Halbleiter |
KR101402457B1 (ko) | 2011-08-19 | 2014-06-11 | 단국대학교 산학협력단 | N-헤테로고리 방향족 화합물과 이온성 액체의 복합체를 포함하는 형광체 및 이의 제조방법 |
EP2688119A1 (en) * | 2012-07-20 | 2014-01-22 | OSRAM GmbH | Organic electroluminescent device and a method of operating an organic electroluminescent device |
ES2625414T3 (es) | 2012-08-02 | 2017-07-19 | F. Hoffmann-La Roche Ag | Nuevos complejos basados en iridio para ECL |
ES2622998T3 (es) | 2012-08-02 | 2017-07-10 | F. Hoffmann-La Roche Ag | Nuevos complejos basados en iridio para EQL |
CN104769077B (zh) | 2012-08-02 | 2017-08-08 | 霍夫曼-拉罗奇有限公司 | 用于ecl的新型铱基配合物 |
EP2880123B1 (en) | 2012-08-02 | 2016-10-05 | Roche Diagnostics GmbH | New iridium-based complexes for ecl |
WO2014019710A1 (en) | 2012-08-02 | 2014-02-06 | Roche Diagnostics Gmbh | New bis-iridium-complexes for manufacturing of ecl-labels |
US20140291590A1 (en) * | 2013-03-28 | 2014-10-02 | The Board Of Regents Of The University Of Texas System | High performance light emitting devices from ionic transition metal complexes |
US9865824B2 (en) | 2013-11-07 | 2018-01-09 | Industrial Technology Research Institute | Organometallic compound, organic light-emitting device, and lighting device employing the same |
DE102014101650B4 (de) * | 2014-02-11 | 2021-07-08 | Pictiva Displays International Limited | Verfahren zur Herstellung einer organischen Leuchtdiode und organische Leuchtdiode |
US10153441B2 (en) | 2015-03-30 | 2018-12-11 | Industrial Technology Research Institute | Organic metal compound, organic light-emitting device, and lighting device employing the same |
KR101876436B1 (ko) * | 2016-01-25 | 2018-07-13 | 숭실대학교산학협력단 | 발광 소자 및 제조방법 |
KR102123791B1 (ko) * | 2018-03-30 | 2020-06-17 | 연세대학교 산학협력단 | 발광소자소재 및 이를 포함하는 전자장치 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070108891A1 (en) * | 2005-11-14 | 2007-05-17 | Idemitsu Kosan Co., Ltd. | Metal-complex compound and organic electroluminescence device using the compound |
WO2008000727A1 (de) * | 2006-06-26 | 2008-01-03 | Basf Se | Verwendung von übergangsmetallcarbenkomplexen, die keine cyclometallierung über nicht-carbene enthalten, in oleds |
CN101308905A (zh) * | 2007-05-18 | 2008-11-19 | 富士胶片株式会社 | 有机电致发光器件 |
WO2008141637A2 (de) * | 2007-05-21 | 2008-11-27 | Osram Opto Semiconductors Gmbh | Phosphoreszente metallkomplexverbindung, strahlungsemittierendes bauelement aufweisend eine phosphoreszente metallkomplexverbindung und verfahren zur herstellung einer phosphoreszenten metallkomplexverbindung |
US20090079329A1 (en) * | 2005-04-25 | 2009-03-26 | Fujifilm Corporation | Organic electroluminescent device |
WO2009046266A1 (en) * | 2007-10-04 | 2009-04-09 | Universal Display Corporation | Complexes with tridentate ligands |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4447066A1 (de) * | 1994-12-29 | 1996-07-04 | Hoechst Ag | Heterocyclische Carbene enthaltende Metallkomplexverbindungen |
US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
US7001536B2 (en) | 1999-03-23 | 2006-02-21 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
JP4019144B2 (ja) * | 2003-03-17 | 2007-12-12 | 独立行政法人産業技術総合研究所 | 高分子炭酸エステルの製造方法 |
JP4203732B2 (ja) | 2003-06-12 | 2009-01-07 | ソニー株式会社 | 有機電界発光材料、有機電界発光素子および含複素環イリジウム錯体化合物 |
DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
WO2005024501A1 (en) * | 2003-09-11 | 2005-03-17 | Koninklijke Philips Electronics N.V. | Transparent display device |
DE10358665A1 (de) | 2003-12-12 | 2005-07-07 | Basf Ag | Verwendung von Platin(II)-Komplexen als lumineszierende Materialien in organischen Licht-emittierenden Dioden (OLEDs) |
JP5045100B2 (ja) | 2004-03-31 | 2012-10-10 | 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材料及び有機エレクトロルミネッセンス素子 |
JPWO2005097942A1 (ja) | 2004-03-31 | 2008-02-28 | 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材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US7534505B2 (en) * | 2004-05-18 | 2009-05-19 | The University Of Southern California | Organometallic compounds for use in electroluminescent devices |
US7279704B2 (en) * | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
US7491823B2 (en) * | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
WO2006008976A1 (ja) | 2004-07-16 | 2006-01-26 | Konica Minolta Holdings, Inc. | 白色発光有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
EP1786242B1 (en) | 2004-08-05 | 2014-08-27 | Konica Minolta Holdings, Inc. | Organic electroluminescence device, display apparatus and lighting apparatus |
CN101087863B (zh) * | 2004-12-23 | 2012-06-20 | 西巴特殊化学品控股有限公司 | 具有亲核卡宾配体的电致发光金属络合物 |
WO2006098120A1 (ja) | 2005-03-16 | 2006-09-21 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子 |
WO2006106842A1 (ja) * | 2005-03-31 | 2006-10-12 | Idemitsu Kosan Co., Ltd. | 遷移金属錯体化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
JP5046548B2 (ja) * | 2005-04-25 | 2012-10-10 | 富士フイルム株式会社 | 有機電界発光素子 |
DE602006008475D1 (de) | 2005-06-30 | 2009-09-24 | Koninkl Philips Electronics Nv | Elektrolumineszente metallkomplexe |
KR20080037006A (ko) * | 2005-08-05 | 2008-04-29 | 이데미쓰 고산 가부시키가이샤 | 전이금속 착체화합물 및 그것을 이용한 유기 전기발광 소자 |
JP2007045742A (ja) * | 2005-08-10 | 2007-02-22 | Mitsubishi Chemicals Corp | 遷移金属錯体の製造方法及び遷移金属錯体 |
JPWO2007069542A1 (ja) * | 2005-12-15 | 2009-05-21 | 出光興産株式会社 | 遷移金属錯体化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
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 |
JP4208894B2 (ja) * | 2006-05-15 | 2009-01-14 | 株式会社東芝 | 発光素子 |
US8247574B2 (en) * | 2006-06-26 | 2012-08-21 | Basf Se | Use of PT -and PD-BIS- and tetra-carbon complexes with bridged carbon ligands in OLEDs |
WO2008096609A1 (ja) * | 2007-02-05 | 2008-08-14 | Idemitsu Kosan Co., Ltd. | 遷移金属錯体化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2008266163A (ja) * | 2007-04-17 | 2008-11-06 | Idemitsu Kosan Co Ltd | 遷移金属錯体化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
JP5194652B2 (ja) * | 2007-09-03 | 2013-05-08 | 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材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US8106580B2 (en) * | 2007-09-18 | 2012-01-31 | Cornell University | Electrospun light-emitting fibers |
-
2009
- 2009-07-03 DE DE102009031683A patent/DE102009031683A1/de not_active Ceased
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2010
- 2010-05-05 WO PCT/EP2010/056111 patent/WO2011000616A1/de active Application Filing
- 2010-05-05 US US13/381,978 patent/US20120169213A1/en not_active Abandoned
- 2010-05-05 KR KR1020127003149A patent/KR101441402B1/ko not_active IP Right Cessation
- 2010-05-05 CN CN201080039437.6A patent/CN102498186B/zh not_active Expired - Fee Related
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090079329A1 (en) * | 2005-04-25 | 2009-03-26 | Fujifilm Corporation | Organic electroluminescent device |
US20070108891A1 (en) * | 2005-11-14 | 2007-05-17 | Idemitsu Kosan Co., Ltd. | Metal-complex compound and organic electroluminescence device using the compound |
WO2008000727A1 (de) * | 2006-06-26 | 2008-01-03 | Basf Se | Verwendung von übergangsmetallcarbenkomplexen, die keine cyclometallierung über nicht-carbene enthalten, in oleds |
CN101308905A (zh) * | 2007-05-18 | 2008-11-19 | 富士胶片株式会社 | 有机电致发光器件 |
WO2008141637A2 (de) * | 2007-05-21 | 2008-11-27 | Osram Opto Semiconductors Gmbh | Phosphoreszente metallkomplexverbindung, strahlungsemittierendes bauelement aufweisend eine phosphoreszente metallkomplexverbindung und verfahren zur herstellung einer phosphoreszenten metallkomplexverbindung |
WO2009046266A1 (en) * | 2007-10-04 | 2009-04-09 | Universal Display Corporation | Complexes with tridentate ligands |
Non-Patent Citations (1)
Title |
---|
李永舫: "聚合物发光电化学池的研究———中国科学院有机固体重点实验室导电聚合物电化学研究工作简介(II)", 《电化学》, vol. 11, no. 1, 28 February 2005 (2005-02-28), pages 1 - 7 * |
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JP5705218B2 (ja) | 2015-04-22 |
WO2011000616A1 (de) | 2011-01-06 |
KR20120048602A (ko) | 2012-05-15 |
EP2718394A1 (de) | 2014-04-16 |
US20120169213A1 (en) | 2012-07-05 |
JP2012531473A (ja) | 2012-12-10 |
KR101441402B1 (ko) | 2014-09-17 |
DE102009031683A1 (de) | 2011-03-24 |
CN102498186B (zh) | 2014-12-03 |
EP2718394B1 (de) | 2015-08-26 |
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