TW200907022A - Chrysenes for green luminescent applications - Google Patents
Chrysenes for green luminescent applications Download PDFInfo
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- TW200907022A TW200907022A TW097120398A TW97120398A TW200907022A TW 200907022 A TW200907022 A TW 200907022A TW 097120398 A TW097120398 A TW 097120398A TW 97120398 A TW97120398 A TW 97120398A TW 200907022 A TW200907022 A TW 200907022A
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- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/48—Chrysenes; Hydrogenated chrysenes
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/86—Ring systems containing bridged rings containing four rings
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US8465848B2 (en) | 2006-12-29 | 2013-06-18 | E I Du Pont De Nemours And Company | Benzofluorenes for luminescent applications |
| ATE536340T1 (de) * | 2007-06-01 | 2011-12-15 | Du Pont | Blaue lumineszente materialien |
| CN101679207B (zh) * | 2007-06-01 | 2014-05-28 | E.I.内穆尔杜邦公司 | 用于深蓝色发光应用的* |
| CN101918512B (zh) | 2007-06-01 | 2014-09-24 | E.I.内穆尔杜邦公司 | 绿色发光材料 |
| KR101443424B1 (ko) | 2008-03-19 | 2014-09-24 | 이데미쓰 고산 가부시키가이샤 | 안트라센 유도체, 발광 재료 및 유기 전기발광 소자 |
| JP5687628B2 (ja) * | 2008-11-19 | 2015-03-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | 青色または緑色ルミネセンス用途のクリセン化合物 |
| US8263973B2 (en) * | 2008-12-19 | 2012-09-11 | E I Du Pont De Nemours And Company | Anthracene compounds for luminescent applications |
| US8531100B2 (en) | 2008-12-22 | 2013-09-10 | E I Du Pont De Nemours And Company | Deuterated compounds for luminescent applications |
| US8759818B2 (en) | 2009-02-27 | 2014-06-24 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
| WO2010114583A1 (en) | 2009-04-03 | 2010-10-07 | E. I. Du Pont De Nemours And Company | Electroactive materials |
| KR101217979B1 (ko) | 2009-04-24 | 2013-01-02 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체를 이용한 유기 전계 발광 소자 |
| EP2669351A1 (en) | 2009-05-19 | 2013-12-04 | E. I. du Pont de Nemours and Company | Chrysene compounds for luminescent applications |
| US9153790B2 (en) | 2009-05-22 | 2015-10-06 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| JP2012532111A (ja) | 2009-07-01 | 2012-12-13 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ルミネセンス用途のクリセン化合物 |
| JP5727478B2 (ja) | 2009-07-27 | 2015-06-03 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | 閉じ込め層を製作するための方法および物質ならびにそれによって製作されるデバイス |
| TW201105615A (en) * | 2009-08-13 | 2011-02-16 | Du Pont | Chrysene derivative materials |
| KR20120091144A (ko) | 2009-09-29 | 2012-08-17 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 발광 응용을 위한 중수소화된 화합물 |
| EP2493887A4 (en) | 2009-10-29 | 2013-06-19 | Du Pont | DETERERATED COMPOUNDS FOR ELECTRONIC APPLICATIONS |
| JP5478615B2 (ja) * | 2009-12-16 | 2014-04-23 | 出光興産株式会社 | 有機発光媒体 |
| US8617720B2 (en) | 2009-12-21 | 2013-12-31 | E I Du Pont De Nemours And Company | Electroactive composition and electronic device made with the composition |
| US20110147717A1 (en) * | 2009-12-21 | 2011-06-23 | E. I. Du Pont De Nemours And Company | Deuterated compounds for luminescent applications |
| EP2655547A1 (en) | 2010-12-20 | 2013-10-30 | E.I. Du Pont De Nemours And Company | Compositions for electronic applications |
| JP6371304B2 (ja) | 2012-12-13 | 2018-08-08 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | 閉じ込め層およびそれを使って製造されるデバイスを製造するための方法および材料 |
| CN103540313B (zh) * | 2013-10-23 | 2015-06-03 | 烟台万润精细化工股份有限公司 | 一种电致发光材料及其应用 |
| CN103664495B (zh) * | 2013-12-10 | 2016-07-06 | 京东方科技集团股份有限公司 | 蒽类衍生物及制备方法、应用和有机发光器件 |
Family Cites Families (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH598927A5 (enExample) * | 1974-10-24 | 1978-05-12 | Hans Bieri | |
| US4053311A (en) * | 1976-04-02 | 1977-10-11 | Limburg William W | Poly-n-vinylcarbazole image transport layer plasticized by bis(4-diethylamino-2-methylphenyl)phenylmethane |
| GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| DE69110922T2 (de) | 1990-02-23 | 1995-12-07 | Sumitomo Chemical Co | Organisch elektrolumineszente Vorrichtung. |
| US5408109A (en) * | 1991-02-27 | 1995-04-18 | The Regents Of The University Of California | Visible light emitting diodes fabricated from soluble semiconducting polymers |
| US5378519A (en) * | 1992-04-28 | 1995-01-03 | Canon Kabushiki Kaisha | Electroluminescent device |
| US6303238B1 (en) * | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
| KR20050084516A (ko) * | 1998-12-28 | 2005-08-26 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자 |
| US6670645B2 (en) * | 2000-06-30 | 2003-12-30 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| US7476452B2 (en) * | 2000-06-30 | 2009-01-13 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds |
| US7276726B2 (en) * | 2000-06-30 | 2007-10-02 | E.I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| JP2002012861A (ja) * | 2000-07-03 | 2002-01-15 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用発光材料およびそれを使用した有機エレクトロルミネッセンス素子 |
| US6579630B2 (en) * | 2000-12-07 | 2003-06-17 | Canon Kabushiki Kaisha | Deuterated semiconducting organic compounds used for opto-electronic devices |
| DE60225274T2 (de) * | 2001-05-21 | 2009-03-26 | F. Hoffmann-La Roche Ag | Chinolinderivate als liganden für den neuropeptid-y-rezeptor |
| US20060159838A1 (en) * | 2005-01-14 | 2006-07-20 | Cabot Corporation | Controlling ink migration during the formation of printable electronic features |
| JP4161262B2 (ja) * | 2002-06-26 | 2008-10-08 | ソニー株式会社 | 有機電界発光素子、及びそれを用いた発光又は表示装置 |
| EP1541657B2 (en) * | 2002-07-19 | 2014-03-05 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent devices and organic luminescent medium |
| TW200404054A (en) * | 2002-07-26 | 2004-03-16 | Wako Pure Chem Ind Ltd | Method for deuteration of aromatic ring |
| CN100340630C (zh) * | 2002-08-16 | 2007-10-03 | 南加利福尼亚大学 | 有机发光材料和器件 |
| CN101628847B (zh) * | 2002-08-23 | 2013-05-29 | 出光兴产株式会社 | 有机电致发光器件和蒽衍生物 |
| JP4164317B2 (ja) * | 2002-08-28 | 2008-10-15 | キヤノン株式会社 | 有機発光素子 |
| KR101148285B1 (ko) * | 2002-09-24 | 2012-05-21 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전기적 응용을 위한 중합체성 산 콜로이드로 제조된수분산성 폴리아닐린 |
| JP4509787B2 (ja) * | 2002-09-24 | 2010-07-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ポリマー酸コロイドを伴って製造される水分散性ポリチオフェン |
| DE60333214D1 (de) * | 2002-11-12 | 2010-08-12 | Idemitsu Kosan Co | Stoff für organische elektrolumineszenzvorrichtung und darauf basierende organische elektrolumineszenzvorrichtung |
| US6872475B2 (en) * | 2002-12-03 | 2005-03-29 | Canon Kabushiki Kaisha | Binaphthalene derivatives for organic electro-luminescent devices |
| US7651788B2 (en) * | 2003-03-05 | 2010-01-26 | Lg Display Co., Ltd. | Organic electroluminescent device |
| DE10328627A1 (de) * | 2003-06-26 | 2005-02-17 | Covion Organic Semiconductors Gmbh | Neue Materialien für die Elektrolumineszenz |
| JP4035482B2 (ja) * | 2003-06-27 | 2008-01-23 | キヤノン株式会社 | 置換アントリル誘導体およびそれを使用した有機発光素子 |
| JP3840235B2 (ja) * | 2003-06-27 | 2006-11-01 | キヤノン株式会社 | 有機発光素子 |
| JP3848306B2 (ja) * | 2003-06-27 | 2006-11-22 | キヤノン株式会社 | アントリル誘導基置換化合物およびそれを使用した有機発光素子 |
| JP3848307B2 (ja) * | 2003-06-27 | 2006-11-22 | キヤノン株式会社 | アミノアントリル誘導基置換化合物およびそれを使用した有機発光素子 |
| US6852429B1 (en) * | 2003-08-06 | 2005-02-08 | Canon Kabushiki Kaisha | Organic electroluminescent device based on pyrene derivatives |
| US6875524B2 (en) * | 2003-08-20 | 2005-04-05 | Eastman Kodak Company | White light-emitting device with improved doping |
| EP1718124A4 (en) * | 2004-02-19 | 2009-06-24 | Idemitsu Kosan Co | ORGANIC ELECTROLUMINESCENCE ELEMENT FOR WHITE COLOR |
| US7365230B2 (en) * | 2004-02-20 | 2008-04-29 | E.I. Du Pont De Nemours And Company | Cross-linkable polymers and electronic devices made with such polymers |
| US7351358B2 (en) * | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
| US20050245752A1 (en) * | 2004-04-29 | 2005-11-03 | Eastman Kodak Company | Synthesis of unsymmetric anthracene compounds |
| TWI373506B (en) * | 2004-05-21 | 2012-10-01 | Toray Industries | Light-emitting element material and light-emitting material |
| EP1753271A4 (en) * | 2004-05-27 | 2009-01-28 | Idemitsu Kosan Co | WHITE ORGANIC ELECTROLUMINESCENT DEVICE |
| US7402681B2 (en) * | 2004-12-14 | 2008-07-22 | Xerox Corporation | Compound with indolocarbazole moieties and devices containing such compound |
| WO2006025273A1 (ja) * | 2004-08-31 | 2006-03-09 | Idemitsu Kosan Co., Ltd. | 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 |
| KR100721565B1 (ko) * | 2004-11-17 | 2007-05-23 | 삼성에스디아이 주식회사 | 저분자 유기 전계 발광 소자 및 그의 제조 방법 |
| JP4429149B2 (ja) * | 2004-11-26 | 2010-03-10 | キヤノン株式会社 | フルオレン化合物及び有機発光素子 |
| JP4599142B2 (ja) * | 2004-11-26 | 2010-12-15 | キヤノン株式会社 | 有機発光素子 |
| JP4955971B2 (ja) * | 2004-11-26 | 2012-06-20 | キヤノン株式会社 | アミノアントリル誘導基置換ピレン化合物および有機発光素子 |
| JP4653469B2 (ja) * | 2004-12-01 | 2011-03-16 | 出光興産株式会社 | 有機電界発光素子 |
| KR101367616B1 (ko) * | 2004-12-28 | 2014-02-27 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 안트라센 유도체, 및 이를 이용한 발광 소자, 발광 장치, 및 전자 기기 |
| EP1847525B1 (en) * | 2005-02-07 | 2010-12-15 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent device using same |
| 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 |
| WO2006103848A1 (ja) * | 2005-03-25 | 2006-10-05 | Idemitsu Kosan Co., Ltd. | 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 |
| KR100739498B1 (ko) * | 2005-05-07 | 2007-07-19 | 주식회사 두산 | 중수소화된 신규 아릴아민 유도체, 그 제조 방법 및 이를이용한 유기 전계 발광 소자 |
| EP1910289A4 (en) * | 2005-08-04 | 2010-06-09 | Semiconductor Energy Lab | CARBAZOLE DERIVATIVE, MATERIAL FOR LIGHT EMITTING ELEMENT OBTAINED USING THE CARBAZOLE DERIVATIVE, LIGHT EMITTING ELEMENT, AND ELECTRONIC DEVICE |
| JP2007137837A (ja) * | 2005-11-21 | 2007-06-07 | Idemitsu Kosan Co Ltd | 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 |
| JP2007230960A (ja) * | 2006-03-03 | 2007-09-13 | Idemitsu Kosan Co Ltd | 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 |
| EP1996540B1 (en) * | 2006-03-23 | 2015-07-08 | LG Chem, Ltd. | New diamine derivatives, preparation method thereof and organic electronic device using the same |
| JP5292287B2 (ja) * | 2006-06-05 | 2013-09-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機電子デバイスの製造方法 |
| US8242223B2 (en) * | 2006-08-24 | 2012-08-14 | E I Du Pont De Nemours And Company | Hole transport polymers |
| WO2008038607A1 (en) * | 2006-09-28 | 2008-04-03 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene derivative, and light emitting element, light emitting device, and electronic device using the anthracene derivative |
| JP2008270737A (ja) * | 2007-03-23 | 2008-11-06 | Fujifilm Corp | 有機電界発光素子 |
| JP5484690B2 (ja) * | 2007-05-18 | 2014-05-07 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
| JP5351018B2 (ja) * | 2007-05-21 | 2013-11-27 | 出光興産株式会社 | アントラセン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
| DE102007024850A1 (de) * | 2007-05-29 | 2008-12-04 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
| US20080303425A1 (en) * | 2007-06-01 | 2008-12-11 | Vsevolod Rostovtsev | Chrysenes for blue luminescent applications |
| JP2009076865A (ja) * | 2007-08-29 | 2009-04-09 | Fujifilm Corp | 有機電界発光素子 |
| US8617720B2 (en) * | 2009-12-21 | 2013-12-31 | E I Du Pont De Nemours And Company | Electroactive composition and electronic device made with the composition |
-
2008
- 2008-05-30 JP JP2010510499A patent/JP5401449B2/ja not_active Expired - Fee Related
- 2008-05-30 EP EP08769836A patent/EP2150599B1/en not_active Not-in-force
- 2008-05-30 WO PCT/US2008/065187 patent/WO2008150940A1/en not_active Ceased
- 2008-05-30 US US12/129,753 patent/US20080303428A1/en not_active Abandoned
- 2008-05-30 TW TW097120398A patent/TW200907022A/zh unknown
- 2008-05-30 CN CN2008800167106A patent/CN101679853B/zh not_active Expired - Fee Related
- 2008-05-30 KR KR1020097027390A patent/KR20100024451A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN101679853A (zh) | 2010-03-24 |
| EP2150599A1 (en) | 2010-02-10 |
| JP5401449B2 (ja) | 2014-01-29 |
| KR20100024451A (ko) | 2010-03-05 |
| JP2010529036A (ja) | 2010-08-26 |
| US20080303428A1 (en) | 2008-12-11 |
| EP2150599B1 (en) | 2012-11-28 |
| WO2008150940A1 (en) | 2008-12-11 |
| CN101679853B (zh) | 2013-10-30 |
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