TWI363792B - Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds - Google Patents

Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds Download PDF

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Publication number
TWI363792B
TWI363792B TW094102739A TW94102739A TWI363792B TW I363792 B TWI363792 B TW I363792B TW 094102739 A TW094102739 A TW 094102739A TW 94102739 A TW94102739 A TW 94102739A TW I363792 B TWI363792 B TW I363792B
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group
ligand
compound
formula
layer
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TW094102739A
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TW200604312A (en
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Kerwin D Dobbs
Norman Herron
Viacheslav A Petrov
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Du Pont
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30Coordination compounds
    • H10K85/341Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18Metal complexes
    • C09K2211/185Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00Properties of the organic materials covered by group H10K85/00
    • H10K2101/10Triplet emission
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/917Electroluminescent

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
TW094102739A 2004-01-30 2005-01-28 Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds TWI363792B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US76829804A 2004-01-30 2004-01-30
US10/774,286 US7476452B2 (en) 2000-06-30 2004-02-06 Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds

Publications (2)

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TW200604312A TW200604312A (en) 2006-02-01
TWI363792B true TWI363792B (en) 2012-05-11

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US (1) US7476452B2 (https=)
JP (1) JP4918365B2 (https=)
TW (1) TWI363792B (https=)
WO (1) WO2005075597A2 (https=)

Families Citing this family (69)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US7816016B1 (en) 2003-02-13 2010-10-19 E. I. Du Pont De Nemours And Company Electroluminescent iridium compounds and devices made therefrom
SE528408C2 (sv) * 2005-03-07 2006-11-07 Interactive Inst Ii Ab En metod och en anordning för visuell indikering av ström- eller effektförbrukning i en elkabel
CN101238138B (zh) 2005-06-30 2012-12-19 皇家飞利浦电子股份有限公司 电致发光金属配合物
JP2007059783A (ja) * 2005-08-26 2007-03-08 Showa Denko Kk 有機el素子、その製造方法およびその用途
US8115378B2 (en) * 2006-12-28 2012-02-14 E. I. Du Pont De Nemours And Company Tetra-substituted chrysenes for luminescent applications
US8257836B2 (en) 2006-12-29 2012-09-04 E I Du Pont De Nemours And Company Di-substituted pyrenes for luminescent applications
EP2147006B1 (en) * 2007-05-18 2015-10-28 Semiconductor Energy Laboratory Co, Ltd. Organometallic complex, composition and light emitting element including the organometallic complex
WO2008150940A1 (en) * 2007-06-01 2008-12-11 E. I. Du Pont De Nemours And Company Chrysenes for green luminescent applications
WO2008150828A2 (en) 2007-06-01 2008-12-11 E.I. Du Pont De Nemours And Company Green luminescent materials
TW200907021A (en) * 2007-06-01 2009-02-16 Du Pont Blue luminescent materials
WO2008150872A1 (en) 2007-06-01 2008-12-11 E.I. Du Pont De Nemours And Company Chrysenes for deep blue luminescent applications
TW200911821A (en) * 2007-06-08 2009-03-16 Solvay Light emitting material
US8192848B2 (en) 2008-01-11 2012-06-05 E I Du Pont De Nemours And Company Substituted pyrenes and associated production methods for luminescent applications
JP5609022B2 (ja) * 2008-06-23 2014-10-22 住友化学株式会社 金属錯体の残基を含む高分子化合物及びそれを用いた素子
US8546844B2 (en) 2008-06-26 2013-10-01 E I Du Pont De Nemours And Company Process for forming an organic light-emitting diode luminaires having a single light-emitting layer with at least two light-emitting dopants
WO2009158558A2 (en) * 2008-06-26 2009-12-30 E. I. Du Pont De Nemours And Company Organic light-emitting diode luminaires
EP2350230A4 (en) * 2008-11-19 2012-08-22 Du Pont CHRYSENE COMPOUNDS FOR BLUE OR GREEN LUMINESCENCE APPLICATIONS
US8932733B2 (en) * 2008-12-19 2015-01-13 E I Du Pont De Nemours And Company Chrysene derivative host materials
US8263973B2 (en) * 2008-12-19 2012-09-11 E I Du Pont De Nemours And Company Anthracene compounds for luminescent applications
WO2010075411A2 (en) * 2008-12-22 2010-07-01 E. I. Du Pont De Nemours And Company Photoactive composition and electronic device made with the composition
US8531100B2 (en) 2008-12-22 2013-09-10 E I Du Pont De Nemours And Company Deuterated compounds for luminescent applications
EP2393820A4 (en) * 2009-02-06 2013-03-13 Solvay IRIDIUM COMPLEX EMITTING PHOSPHORESCENT LIGHT CONTAINING LIGAND PYRIDYLTRIAZOLE
US8759818B2 (en) 2009-02-27 2014-06-24 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
EP2414481A4 (en) 2009-04-03 2013-02-20 Du Pont ELECTROACTIVE MATERIALS
JP2012527470A (ja) 2009-05-19 2012-11-08 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
US9133095B2 (en) 2009-07-01 2015-09-15 E I Du Pont De Nemours And Company Chrysene compounds for luminescent applications
TW201105615A (en) * 2009-08-13 2011-02-16 Du Pont Chrysene derivative materials
KR20120066025A (ko) * 2009-08-24 2012-06-21 이 아이 듀폰 디 네모아 앤드 캄파니 유기 발광 다이오드 조명기구
KR20120068881A (ko) * 2009-08-24 2012-06-27 이 아이 듀폰 디 네모아 앤드 캄파니 유기 발광 다이오드 조명기구
US20110204335A1 (en) * 2009-08-24 2011-08-25 E. I. Du Pont De Nemours And Company Organic light-emitting diode luminaires
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EP2471120A2 (en) * 2009-08-24 2012-07-04 E. I. du Pont de Nemours and Company Organic light-emitting diode luminaires
TW201117649A (en) * 2009-08-24 2011-05-16 Du Pont Organic light-emitting diode luminaires
KR101790854B1 (ko) 2009-09-29 2017-10-26 이 아이 듀폰 디 네모아 앤드 캄파니 발광 응용을 위한 중수소화된 화합물
CN102574773B (zh) 2009-10-19 2014-09-17 E.I.内穆尔杜邦公司 用于电子应用的三芳基胺化合物
JP2013508375A (ja) 2009-10-19 2013-03-07 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 電子用途用のトリアリールアミン化合物
US8716699B2 (en) 2009-10-29 2014-05-06 E I Du Pont De Nemours And Company Organic light-emitting diodes having white light emission
US8674343B2 (en) 2009-10-29 2014-03-18 E I Du Pont De Nemours And Company Organic light-emitting diodes having white light emission
US8716700B2 (en) 2009-10-29 2014-05-06 E I Du Pont De Nemours And Company Organic light-emitting diodes having white light emission
US20110101312A1 (en) * 2009-10-29 2011-05-05 E. I. Du Pont De Nemours And Company Deuterated compounds for electronic applications
US20110133632A1 (en) * 2009-12-09 2011-06-09 E.I. Du Pont De Nemours And Company Deuterated compound as part of a combination of compounds for electronic applications
US8465849B2 (en) * 2009-12-21 2013-06-18 E I Du Pont De Nemours And Company Deuterated zirconium compound for electronic applications
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
TW201213277A (en) 2010-08-11 2012-04-01 Du Pont Electroactive compound and composition and electronic device made with the composition
TW201211204A (en) 2010-08-24 2012-03-16 Du Pont Photoactive composition and electronic device made with the composition
CN102408448B (zh) * 2010-09-21 2015-04-15 中国科学院福建物质结构研究所 一种检测次氯酸根的磷光材料
TW201229010A (en) 2010-12-13 2012-07-16 Du Pont Electroactive materials
US9269909B2 (en) 2010-12-15 2016-02-23 E I Du Pont De Nemours And Company Electroactive material and devices made with such materials
TW201229204A (en) 2010-12-17 2012-07-16 Du Pont Anthracene derivative compounds for electronic applications
TW201229003A (en) 2010-12-17 2012-07-16 Du Pont Anthracene derivative compounds for electronic applications
WO2012083301A1 (en) 2010-12-17 2012-06-21 E. I. Du Pont De Nemours And Company Anthracene derivative compounds for electronic applications
JP5727038B2 (ja) 2010-12-20 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 電子技術応用のための組成物
JP2014509068A (ja) 2010-12-20 2014-04-10 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 電子技術応用のための電気活性組成物
WO2012087960A1 (en) 2010-12-20 2012-06-28 E. I. Du Pont De Nemours And Company Triazine derivatives for electronic applications
US20130256646A1 (en) 2010-12-21 2013-10-03 E I Du Pont De Nemours And Company Electronic device including a pyrimidine compound
WO2013059718A1 (en) 2011-10-19 2013-04-25 E. I. Du Pont De Nemours And Company Organic electronic device for lighting
JP2012039161A (ja) * 2011-11-22 2012-02-23 Konica Minolta Holdings Inc 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
EP2828273B1 (en) * 2012-03-23 2019-02-20 E. I. du Pont de Nemours and Company Green luminescent materials
JP2014529897A (ja) * 2012-04-30 2014-11-13 ヨル チョン ケミカル カンパニーリミテッドYoul Chon Chemical Co., Ltd. 新規な金属錯化合物及びそれを含む青色燐光有機発光素子
KR102065586B1 (ko) 2013-01-30 2020-01-14 삼성디스플레이 주식회사 유기금속 착체 및 이를 포함한 유기 발광 소자
KR102037375B1 (ko) 2013-02-13 2019-10-29 삼성디스플레이 주식회사 유기금속 착체 및 이를 포함한 유기 발광 소자
WO2014130597A1 (en) 2013-02-25 2014-08-28 E. I. Du Pont De Nemours And Company Electronic device including a diazachrysene derivative
KR102216743B1 (ko) 2013-12-13 2021-02-16 주식회사 엘지화학 전기활성 층을 형성하기 위한 시스템
US9944846B2 (en) 2014-08-28 2018-04-17 E I Du Pont De Nemours And Company Compositions for electronic applications
US9972783B2 (en) 2015-03-25 2018-05-15 E I Du Pont De Nemours And Company High energy triarylamine compounds for hole transport materials
US10804473B2 (en) 2015-05-21 2020-10-13 Lg Chem, Ltd. Electron transport materials for electronic applications
US9966542B2 (en) 2016-06-02 2018-05-08 E I Du Pont De Nemours And Company Electroactive materials
RU2657496C1 (ru) * 2017-07-10 2018-06-14 Сиа Эволед Разнолигандные фторзамещенные ароматические карбоксилаты лантанидов, проявляющие люминесцентные свойства, и органические светодиоды на их основе

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59507438D1 (de) 1994-07-25 2000-01-20 Roche Diagnostics Gmbh Hydrophile metallkomplexe
US5552678A (en) * 1994-09-23 1996-09-03 Eastman Kodak Company AC drive scheme for organic led
US6303238B1 (en) * 1997-12-01 2001-10-16 The Trustees Of Princeton University OLEDs doped with phosphorescent compounds
CN1226902C (zh) 1999-03-23 2005-11-09 南加利福尼亚大学 在有机发光装置中用作磷光掺杂剂的环金属化金属配合物
CN101312235B (zh) 1999-05-13 2010-06-09 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
JP4357781B2 (ja) 1999-12-01 2009-11-04 ザ、トラスティーズ オブ プリンストン ユニバーシティ 有機led用燐光性ドーパントとしての式l2mxの錯体
US6821645B2 (en) * 1999-12-27 2004-11-23 Fuji Photo Film Co., Ltd. Light-emitting material comprising orthometalated iridium complex, light-emitting device, high efficiency red light-emitting device, and novel iridium complex
JP4048521B2 (ja) * 2000-05-02 2008-02-20 富士フイルム株式会社 発光素子
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
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
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
US7306856B2 (en) * 2000-07-17 2007-12-11 Fujifilm Corporation Light-emitting element and iridium complex
EP1175128B1 (en) 2000-07-17 2010-09-22 FUJIFILM Corporation Light emitting element and azole compound
US6939624B2 (en) * 2000-08-11 2005-09-06 Universal Display Corporation Organometallic compounds and emission-shifting organic electrophosphorescence
JP5241053B2 (ja) 2000-08-11 2013-07-17 ザ、トラスティーズ オブ プリンストン ユニバーシティ 有機金属化合物及び放射移行有機電気燐光体
JP4154140B2 (ja) 2000-09-26 2008-09-24 キヤノン株式会社 金属配位化合物
CN1285601C (zh) 2000-11-30 2006-11-22 佳能株式会社 发光器件和显示器
AU2002222565A1 (en) * 2000-11-30 2002-06-11 Canon Kabushiki Kaisha Luminescent element and display
JP3812730B2 (ja) * 2001-02-01 2006-08-23 富士写真フイルム株式会社 遷移金属錯体及び発光素子
US7320833B2 (en) * 2001-11-07 2008-01-22 E.I. Du Pont De Nemours And Company Electroluminescent platinum compounds and devices made with such compounds
US7166368B2 (en) 2001-11-07 2007-01-23 E. I. Du Pont De Nemours And Company Electroluminescent platinum compounds and devices made with such compounds
CA2455844A1 (en) 2001-12-26 2003-07-31 Viacheslav A. Petrov Electroluminescent iridium compounds wiht fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
US6869695B2 (en) * 2001-12-28 2005-03-22 The Trustees Of Princeton University White light emitting OLEDs from combined monomer and aggregate emission
US6919139B2 (en) 2002-02-14 2005-07-19 E. I. Du Pont De Nemours And Company Electroluminescent iridium compounds with phosphinoalkoxides and phenylpyridines or phenylpyrimidines and devices made with such compounds
DE10215010A1 (de) 2002-04-05 2003-10-23 Covion Organic Semiconductors Rhodium- und Iridium-Komplexe
US7011897B2 (en) * 2002-08-16 2006-03-14 The University Of Southern California Organic light emitting materials and devices
US6916554B2 (en) * 2002-11-06 2005-07-12 The University Of Southern California Organic light emitting materials and devices
KR101016164B1 (ko) * 2002-10-09 2011-02-17 이데미쓰 고산 가부시키가이샤 유기 전기발광 소자
KR100682858B1 (ko) * 2003-06-26 2007-02-15 삼성에스디아이 주식회사 유기 금속 착물 및 이를 채용한 유기 전계 발광 소자
US7198730B2 (en) * 2003-08-28 2007-04-03 E. I. Du Pont De Nemours And Company Phosphorescent material
JP4438394B2 (ja) * 2003-10-30 2010-03-24 三菱化学株式会社 有機金属錯体およびそれを用いた有機電界発光素子

Also Published As

Publication number Publication date
JP2007524239A (ja) 2007-08-23
JP4918365B2 (ja) 2012-04-18
US20050037233A1 (en) 2005-02-17
US20070292713A9 (en) 2007-12-20
WO2005075597A2 (en) 2005-08-18
US7476452B2 (en) 2009-01-13
TW200604312A (en) 2006-02-01
WO2005075597A3 (en) 2005-12-01

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