CA2455844A1 - Electroluminescent iridium compounds wiht fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds - Google Patents

Electroluminescent iridium compounds wiht fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds Download PDF

Info

Publication number
CA2455844A1
CA2455844A1 CA002455844A CA2455844A CA2455844A1 CA 2455844 A1 CA2455844 A1 CA 2455844A1 CA 002455844 A CA002455844 A CA 002455844A CA 2455844 A CA2455844 A CA 2455844A CA 2455844 A1 CA2455844 A1 CA 2455844A1
Authority
CA
Canada
Prior art keywords
compound
compounds
layer
formula
nmr
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002455844A
Other languages
English (en)
French (fr)
Inventor
Viacheslav A. Petrov
Ying Wang
Vladimir Grushin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2455844A1 publication Critical patent/CA2455844A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/68—One oxygen atom attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • 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 [2D] radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional [2D] 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Pyridine Compounds (AREA)
  • Quinoline Compounds (AREA)
CA002455844A 2001-12-26 2001-12-26 Electroluminescent iridium compounds wiht fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds Abandoned CA2455844A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2001/049522 WO2003063555A1 (en) 2001-12-26 2001-12-26 Electroluminescent iridium compounds wiht fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds

Publications (1)

Publication Number Publication Date
CA2455844A1 true CA2455844A1 (en) 2003-07-31

Family

ID=32228276

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002455844A Abandoned CA2455844A1 (en) 2001-12-26 2001-12-26 Electroluminescent iridium compounds wiht fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds

Country Status (7)

Country Link
EP (4) EP2306789A1 (https=)
JP (1) JP4299144B2 (https=)
KR (1) KR100879695B1 (https=)
CN (1) CN1520702B (https=)
CA (1) CA2455844A1 (https=)
IL (1) IL158314A0 (https=)
WO (1) WO2003063555A1 (https=)

Families Citing this family (163)

* 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
CN1285601C (zh) 2000-11-30 2006-11-22 佳能株式会社 发光器件和显示器
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
US7250512B2 (en) 2001-11-07 2007-07-31 E. I. Du Pont De Nemours And Company Electroluminescent iridium compounds having red-orange or red emission and devices made with such compounds
JP4464277B2 (ja) 2002-09-24 2010-05-19 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 導電性有機ポリマー／ナノ粒子複合材料およびその使用方法
CA2499364A1 (en) 2002-09-24 2004-04-08 E. I. Du Pont De Nemours And Company Water dispersible polyanilines made with polymeric acid colloids for electronics applications
WO2004029128A2 (en) 2002-09-24 2004-04-08 E.I. Du Pont De Nemours And Company Water dispersible polythiophenes made with polymeric acid colloids
US7317047B2 (en) 2002-09-24 2008-01-08 E.I. Du Pont De Nemours And Company Electrically conducting organic polymer/nanoparticle composites and methods for use thereof
US7816016B1 (en) 2003-02-13 2010-10-19 E. I. Du Pont De Nemours And Company Electroluminescent iridium compounds and devices made therefrom
US7390438B2 (en) 2003-04-22 2008-06-24 E.I. Du Pont De Nemours And Company Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids
KR100718100B1 (ko) 2003-09-06 2007-05-14 삼성에스디아이 주식회사 이핵 유기금속 착물 및 이를 이용한 유기 전계 발광 소자
KR100560790B1 (ko) 2003-11-25 2006-03-13 삼성에스디아이 주식회사 고온 특성이 우수한 유기 전계 발광 표시 장치
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
US8147962B2 (en) 2004-04-13 2012-04-03 E. I. Du Pont De Nemours And Company Conductive polymer composites
KR100574450B1 (ko) 2004-06-03 2006-04-26 동우 화인켐 주식회사 불소계 가지체를 포함하는 유기 전기발광 소자용 발광화합물
CN1305883C (zh) * 2004-06-17 2007-03-21 复旦大学 含芳香胺的铱配合物及其制备方法和应用
KR101030011B1 (ko) * 2004-08-28 2011-04-20 삼성모바일디스플레이주식회사 시클로메탈화 전이금속 착물 및 이를 이용한 유기 전계발광 소자
US7449601B2 (en) 2004-12-16 2008-11-11 E. I. Du Pont De Nemours And Company Catalysts useful for catalyzing the coupling of arylhalides with arylboronic acids
US7504769B2 (en) 2004-12-16 2009-03-17 E. I. Du Pont De Nemours + Company Aromatic chalcogen compounds and their use
US8063551B1 (en) 2004-12-29 2011-11-22 E.I. Du Pont De Nemours And Company Pixel intensity homogeneity in organic electronic devices
US8950328B1 (en) 2004-12-29 2015-02-10 E I Du Pont De Nemours And Company Methods of fabricating organic electronic devices
JP5130606B2 (ja) * 2005-02-25 2013-01-30 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、その製造方法、表示装置及び照明装置
KR100676965B1 (ko) * 2005-03-05 2007-02-02 주식회사 두산 신규 이리듐 착화합물 및 이를 이용한 유기 전계 발광 소자
US7554112B1 (en) 2005-03-10 2009-06-30 E. I. Du Pont De Nemours And Company Organic electronic device and processes for forming and using the same
US7638072B2 (en) 2005-06-27 2009-12-29 E. I. Du Pont De Nemours And Company Electrically conductive polymer compositions
EP1896515A4 (en) 2005-06-27 2010-03-10 Du Pont ELECTRICALLY CONDUCTIVE POLYMER COMPOSITIONS
KR101294892B1 (ko) 2005-06-27 2013-08-09 이 아이 듀폰 디 네모아 앤드 캄파니 전기 전도성 중합체 조성물
US7727421B2 (en) 2005-06-27 2010-06-01 E. I. Du Pont De Nemours And Company Dupont Displays Inc Electrically conductive polymer compositions
EP1897096A4 (en) 2005-06-28 2009-08-12 Du Pont TRANSPARENT LADDER WITH HIGH WORKING FUNCTION
WO2007002740A2 (en) 2005-06-28 2007-01-04 E. I. Du Pont De Nemours And Company Buffer compositions
JP5505382B2 (ja) * 2005-08-01 2014-05-28 三菱化学株式会社 遷移金属錯体の製造方法
US20070170401A1 (en) 2005-12-28 2007-07-26 Che-Hsiung Hsu Cationic compositions of electrically conducting polymers doped with fully-fluorinated acid polymers
US8216680B2 (en) 2006-02-03 2012-07-10 E I Du Pont De Nemours And Company Transparent composite conductors having high work function
US8124172B2 (en) 2006-03-02 2012-02-28 E.I. Du Pont De Nemours And Company Process for making contained layers and devices made with same
US20070278936A1 (en) * 2006-06-02 2007-12-06 Norman Herron Red emitter complexes of IR(III) and devices made with such compounds
WO2007145975A2 (en) 2006-06-05 2007-12-21 E. I. Du Pont De Nemours And Company Process for forming an organic light-emitting diode and devices made by the process
EP2041222B1 (en) 2006-06-30 2012-12-05 E.I. Du Pont De Nemours And Company Stabilized compositions of conductive polymers and partially-fluorinated acid polymers
US7582757B2 (en) 2006-09-06 2009-09-01 E. I. Du Pont De Nemours And Company Electroluminescent complexes of Ir(III) and devices
WO2008063466A2 (en) 2006-11-13 2008-05-29 E. I. Du Pont De Nemours And Company Organic electronic device
US8153029B2 (en) 2006-12-28 2012-04-10 E.I. Du Pont De Nemours And Company Laser (230NM) ablatable compositions of electrically conducting polymers made with a perfluoropolymeric acid applications thereof
US8115378B2 (en) 2006-12-28 2012-02-14 E. I. Du Pont De Nemours And Company Tetra-substituted chrysenes for luminescent applications
US20080191172A1 (en) 2006-12-29 2008-08-14 Che-Hsiung Hsu High work-function and high conductivity compositions of electrically conducting polymers
US20080251768A1 (en) 2007-04-13 2008-10-16 Che-Hsiung Hsu Electrically conductive polymer compositions
US8241526B2 (en) 2007-05-18 2012-08-14 E I Du Pont De Nemours And Company Aqueous dispersions of electrically conducting polymers containing high boiling solvent and additives
EP2147006B1 (en) 2007-05-18 2015-10-28 Semiconductor Energy Laboratory Co, Ltd. Organometallic complex, composition and light emitting element including the organometallic complex
WO2008150828A2 (en) 2007-06-01 2008-12-11 E.I. Du Pont De Nemours And Company Green luminescent materials
WO2008150872A1 (en) 2007-06-01 2008-12-11 E.I. Du Pont De Nemours And Company Chrysenes for deep blue luminescent applications
KR101589864B1 (ko) 2007-06-01 2016-01-29 이 아이 듀폰 디 네모아 앤드 캄파니 발광 용도를 위한 전하 수송 재료
KR20100096105A (ko) * 2007-10-23 2010-09-01 이 아이 듀폰 디 네모아 앤드 캄파니 발광 응용을 위한 3중 발광 층
KR20100094475A (ko) 2007-10-26 2010-08-26 이 아이 듀폰 디 네모아 앤드 캄파니 격납된 층을 제조하기 위한 방법 및 재료, 및 이를 사용하여 제조된 소자
US8063399B2 (en) 2007-11-19 2011-11-22 E. I. Du Pont De Nemours And Company Electroactive materials
JP2011507190A (ja) 2007-12-10 2011-03-03 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 多色電子デバイスおよび印刷によるその形成方法
US8040048B2 (en) 2007-12-12 2011-10-18 Lang Charles D Process for forming an organic electronic device including an organic device layer
US8308988B2 (en) 2007-12-17 2012-11-13 E I Du Pont De Nemours And Company Electroactive materials
US8174185B2 (en) 2007-12-21 2012-05-08 E I Du Pont De Nemours And Company Charge transport materials for luminescent applications
KR100966886B1 (ko) * 2008-01-29 2010-06-30 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자
EP2086034A1 (en) 2008-02-01 2009-08-05 Nederlandse Centrale Organisatie Voor Toegepast Natuurwetenschappelijk Onderzoek TNO Electronic device and method of manufacturing thereof
TW201005813A (en) 2008-05-15 2010-02-01 Du Pont Process for forming an electroactive layer
US8216685B2 (en) 2008-05-16 2012-07-10 E I Du Pont De Nemours And Company Buffer bilayers for electronic devices
US8343381B1 (en) 2008-05-16 2013-01-01 E I Du Pont De Nemours And Company Hole transport composition
US8242487B2 (en) 2008-05-16 2012-08-14 E I Du Pont De Nemours And Company Anode for an organic electronic device
US9138771B2 (en) 2008-05-19 2015-09-22 E I Du Pont De Nemours And Company Apparatus and method for solution coating thin layers
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
CN102171852B (zh) 2008-10-21 2013-11-06 E.I.内穆尔杜邦公司 多色电子器件及通过印刷形成该器件的工艺
US8643000B2 (en) 2008-11-18 2014-02-04 E I Du Pont De Nemours And Company Organic electronic device with low-reflectance electrode
US9099653B2 (en) 2008-12-01 2015-08-04 E I Du Pont De Nemours And Company Electroactive materials
KR101564129B1 (ko) 2008-12-01 2015-10-28 이 아이 듀폰 디 네모아 앤드 캄파니 전기활성 재료
US8420232B2 (en) 2008-12-04 2013-04-16 E I Du Pont De Nemours And Company Binaphthyl-arylamine polymers
KR101534371B1 (ko) 2008-12-09 2015-07-06 이 아이 듀폰 디 네모아 앤드 캄파니 전기 전도성 중합체 조성물
JP5628826B2 (ja) 2008-12-09 2014-11-19 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 導電性ポリマー組成物
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
US8461758B2 (en) 2008-12-19 2013-06-11 E I Du Pont De Nemours And Company Buffer bilayers for electronic devices
TW201033207A (en) 2008-12-22 2010-09-16 Du Pont Electronic device including phenanthroline derivative
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
US8278405B2 (en) 2008-12-22 2012-10-02 E I Du Pont De Nemours And Company Vinylphenoxy polymers
US8278651B2 (en) 2008-12-22 2012-10-02 E I Du Pont De Nemours And Company Electronic device including 1,7-phenanthroline derivative
US8531100B2 (en) 2008-12-22 2013-09-10 E I Du Pont De Nemours And Company Deuterated compounds for luminescent applications
WO2010075589A2 (en) 2008-12-27 2010-07-01 E. I. Du Pont De Nemours And Company Apparatus and method for preventing splatter for continuous printing
US8785913B2 (en) 2008-12-27 2014-07-22 E I Du Pont De Nemours And Company Buffer bilayers for electronic devices
US8766239B2 (en) 2008-12-27 2014-07-01 E I Du Pont De Nemours And Company Buffer bilayers for electronic devices
EP2202819A1 (en) 2008-12-29 2010-06-30 Nederlandse Organisatie voor toegepast-natuurwetenschappelijk Onderzoek TNO Electro-optic device and method for manufacturing the same
US8759818B2 (en) 2009-02-27 2014-06-24 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
EP2404315A4 (en) 2009-03-06 2012-08-08 Du Pont METHOD FOR FORMING AN ELECTROACTIVE LAYER
EP2404213A2 (en) 2009-03-06 2012-01-11 E. I. du Pont de Nemours and Company Multicolor electronic devices and processes of forming the same by printing
JP2012519950A (ja) 2009-03-09 2012-08-30 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 電気活性層の形成方法
CN102362338A (zh) 2009-03-09 2012-02-22 E.I.内穆尔杜邦公司 形成电活性层的方法
KR101561402B1 (ko) 2009-03-12 2015-10-16 이 아이 듀폰 디 네모아 앤드 캄파니 코팅 도포를 위한 전기 전도성 중합체 조성물
EP2414481A4 (en) 2009-04-03 2013-02-20 Du Pont ELECTROACTIVE MATERIALS
EP2421918B1 (en) 2009-04-21 2020-08-26 LG Chem, Ltd. Electrically conductive polymer compositions and films made therefrom
TW201100482A (en) 2009-04-24 2011-01-01 Du Pont Electrically conductive polymer compositions and films made therefrom
TWI687408B (zh) * 2009-04-28 2020-03-11 美商環球展覽公司 具有甲基-ｄ３取代之銥錯合物
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
TW201103767A (en) 2009-06-04 2011-02-01 Du Pont Multicolor electronic devices and processes of forming the same by printing
US8619326B2 (en) 2009-06-04 2013-12-31 E I Du Pont De Nemours And Company Multicolor electronic devices and processes of forming the same by printing
US9133095B2 (en) 2009-07-01 2015-09-15 E I Du Pont De Nemours And Company Chrysene compounds for luminescent applications
US8592239B2 (en) 2009-07-27 2013-11-26 E I Du Pont De Nemours And Company Process and materials for making contained layers and devices made with same
EP2284922A1 (en) 2009-08-06 2011-02-16 Nederlandse Organisatie voor toegepast -natuurwetenschappelijk onderzoek TNO Method of manufacturing an opto-electric device
TW201105615A (en) 2009-08-13 2011-02-16 Du Pont Chrysene derivative materials
EP2471122A4 (en) 2009-08-24 2013-11-06 Du Pont OLED LIGHTING
US20110204335A1 (en) * 2009-08-24 2011-08-25 E. I. Du Pont De Nemours And Company Organic light-emitting diode luminaires
KR20120068881A (ko) 2009-08-24 2012-06-27 이 아이 듀폰 디 네모아 앤드 캄파니 유기 발광 다이오드 조명기구
JP5382887B2 (ja) 2009-08-27 2014-01-08 独立行政法人産業技術総合研究所 イリジウム錯体ならびに該化合物からなる発光材料
KR101790854B1 (ko) 2009-09-29 2017-10-26 이 아이 듀폰 디 네모아 앤드 캄파니 발광 응용을 위한 중수소화된 화합물
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
US20110101312A1 (en) 2009-10-29 2011-05-05 E. I. Du Pont De Nemours And Company Deuterated compounds for electronic applications
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
EP2494624A4 (en) 2009-10-29 2014-01-08 Du Pont LIGHT PANELS WITH ORGANIC LIGHT EMITTING DIODES
US8716700B2 (en) 2009-10-29 2014-05-06 E I Du Pont De Nemours And Company Organic light-emitting diodes having white light emission
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
US8282861B2 (en) 2009-12-21 2012-10-09 Che-Hsiung Hsu Electrically conductive polymer compositions
EP2346108A1 (en) 2010-01-15 2011-07-20 Nederlandse Organisatie voor toegepast -natuurwetenschappelijk onderzoek TNO Foil shaped electro-optical product, semi-finished product and method and apparatus for manufacturing the same
TW201200975A (en) 2010-06-17 2012-01-01 Du Pont Process and materials for making contained layers and devices made with same
EP2398086A1 (en) 2010-06-17 2011-12-21 Nederlandse Organisatie voor toegepast -natuurwetenschappelijk onderzoek TNO Opto-electric device and method of manufacturing thereof
TW201204687A (en) 2010-06-17 2012-02-01 Du Pont Electroactive materials
TW201211204A (en) 2010-08-24 2012-03-16 Du Pont Photoactive composition and electronic device made with the composition
TW201230434A (en) 2010-12-01 2012-07-16 Du Pont Organic electronic device with composite electrode
US9269909B2 (en) 2010-12-15 2016-02-23 E I Du Pont De Nemours And Company Electroactive material and devices made with such materials
WO2012087960A1 (en) 2010-12-20 2012-06-28 E. I. Du Pont De Nemours And Company Triazine derivatives for electronic applications
JP5871949B2 (ja) 2010-12-20 2016-03-01 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
JP5844820B2 (ja) 2010-12-20 2016-01-20 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 電気活性材料
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
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
EP2656411A1 (en) 2010-12-21 2013-10-30 E.I. Du Pont De Nemours And Company Liquid composition for deposition of organic electroactive materials
US20130256646A1 (en) 2010-12-21 2013-10-03 E I Du Pont De Nemours And Company Electronic device including a pyrimidine compound
CN103732719B (zh) * 2011-03-10 2015-12-02 国立大学法人九州大学 磷光发光材料、磷光发光材料的制造方法以及磷光发光元件
WO2013059718A1 (en) 2011-10-19 2013-04-25 E. I. Du Pont De Nemours And Company Organic electronic device for lighting
EP2828273B1 (en) 2012-03-23 2019-02-20 E. I. du Pont de Nemours and Company Green luminescent materials
JP2015519306A (ja) 2012-04-02 2015-07-09 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 青色ルミネセンス化合物
US9685618B2 (en) 2012-04-23 2017-06-20 E I Du Pont De Nemours And Company Blue luminescent compounds
US9062993B2 (en) 2012-05-22 2015-06-23 E I Du Pont De Nemours And Company Method and apparatus for liquid flow calibration check
JP6560120B2 (ja) 2012-08-02 2019-08-14 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ Ｅｃｌ製造用の新規ビス−イリジウム錯体
CN104822696B (zh) 2012-08-02 2017-09-22 霍夫曼-拉罗奇有限公司 用于ecl的新型铱基配合物
CA2879087C (en) 2012-08-02 2020-10-27 F. Hoffmann-La Roche Ag Iridium-based complexes for ecl
JP6255017B2 (ja) 2012-08-02 2017-12-27 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ Ｅｃｌ用の新規イリジウムベース錯体
WO2014019709A2 (en) 2012-08-02 2014-02-06 Roche Diagnostics Gmbh New iridium-based complexes for ecl
CN103044490B (zh) * 2012-10-16 2015-10-28 中科院广州化学有限公司 一种新型苯基噌啉类铱配合物及其制备方法与应用
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
WO2014130597A1 (en) 2013-02-25 2014-08-28 E. I. Du Pont De Nemours And Company Electronic device including a diazachrysene derivative
CN103145763B (zh) * 2013-03-02 2016-06-15 大连理工大学 基于吡啶的环金属配体-铂配合物及其制备方法与应用
US10586929B2 (en) 2013-12-12 2020-03-10 Lg Chem, Ltd. Solvent-resistant hole transport layers
KR102216743B1 (ko) 2013-12-13 2021-02-16 주식회사 엘지화학 전기활성 층을 형성하기 위한 시스템
DE112014006141T5 (de) 2014-01-10 2016-10-06 National Institute Of Advanced Industrial Science And Technology Rohmaterial und Herstellungsverfahren für einen cyclometallierten lridiumkomplex
WO2015112561A1 (en) 2014-01-23 2015-07-30 E. I. Du Pont De Nemours And Company Electroactive metal complexes
US9947872B2 (en) 2014-07-15 2018-04-17 E I Du Pont De Nemours And Company Hole transport materials
US9944846B2 (en) 2014-08-28 2018-04-17 E I Du Pont De Nemours And Company Compositions for electronic applications
US10193070B2 (en) 2014-10-31 2019-01-29 E I Du Pont De Nemours And Company Electroactive materials
KR102217267B1 (ko) 2014-11-20 2021-02-17 주식회사 엘지화학 정공수송물질
US9746776B2 (en) 2014-11-25 2017-08-29 E I Du Pont De Nemours And Company Low surface energy photoresist composition and process
WO2016126423A2 (en) 2015-02-03 2016-08-11 E I Du Pont De Nemours And Company Electroactive materials
US9972783B2 (en) 2015-03-25 2018-05-15 E I Du Pont De Nemours And Company High energy triarylamine compounds for hole transport materials
US9662918B2 (en) 2015-04-03 2017-05-30 E I Du Pont De Nemours And Company Gradient ink containment printing process and apparatus
US9954174B2 (en) 2015-05-06 2018-04-24 E I Du Pont De Nemours And Company Hole transport materials
US10804473B2 (en) 2015-05-21 2020-10-13 Lg Chem, Ltd. Electron transport materials for electronic applications
US10897025B2 (en) 2015-05-26 2021-01-19 Lg Chem, Ltd. Electroactive materials
US20170025609A1 (en) 2015-07-20 2017-01-26 E I Du Pont De Nemours And Company Electroactive materials
US9525134B1 (en) 2015-08-11 2016-12-20 E I Du Pont De Nemours And Company Hole transport materials
US10862037B2 (en) 2015-10-16 2020-12-08 Lg Chem, Ltd. Electroactive materials
US9768238B2 (en) 2015-11-16 2017-09-19 E I Du Pont De Nemours And Company Electrical device to mask systematic luminance variation
CN108463465A (zh) 2016-01-14 2018-08-28 国立研究开发法人产业技术综合研究所 环金属化铱配合物的制造方法
KR102290839B1 (ko) 2016-05-27 2021-08-17 주식회사 엘지화학 도전성 중합체 조성물에서의 디헤테로 아민
US9966542B2 (en) 2016-06-02 2018-05-08 E I Du Pont De Nemours And Company Electroactive materials

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH647508A5 (en) * 1981-05-07 1985-01-31 Lonza Ag Process for the preparation of 2-arylpyridines
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
US5552678A (en) 1994-09-23 1996-09-03 Eastman Kodak Company AC drive scheme for organic led
JP3691101B2 (ja) * 1995-01-24 2005-08-31 三洋電機株式会社 有機エレクトロルミネッセンス素子
US5627193A (en) * 1995-02-09 1997-05-06 Mitsui Toatsu Chemicals, Inc. Quinoline-4-carbonylguanidine derivatives, process for producing the same and pharmaceutical preparations containing the compounds
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
JP3929690B2 (ja) * 1999-12-27 2007-06-13 富士フイルム株式会社 オルトメタル化イリジウム錯体からなる発光素子材料、発光素子および新規イリジウム錯体
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
EP1175128B1 (en) * 2000-07-17 2010-09-22 FUJIFILM Corporation Light emitting element and azole compound
JP4712232B2 (ja) * 2000-07-17 2011-06-29 富士フイルム株式会社 発光素子及びアゾール化合物
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
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
CN1285601C (zh) * 2000-11-30 2006-11-22 佳能株式会社 发光器件和显示器
JP2004521915A (ja) * 2001-02-02 2004-07-22 グラクソ　グループ　リミテッド Ｔｇｆ過剰発現に対するピラゾール誘導体
WO2002104080A1 (fr) * 2001-06-15 2002-12-27 Canon Kabushiki Kaisha Dispositif a electroluminescence organique

Also Published As

Publication number Publication date
KR20040069972A (ko) 2004-08-06
JP2005516040A (ja) 2005-06-02
EP1466506A4 (en) 2007-03-07
EP2306788A1 (en) 2011-04-06
EP1466506A1 (en) 2004-10-13
JP4299144B2 (ja) 2009-07-22
EP2306789A1 (en) 2011-04-06
EP2299785A1 (en) 2011-03-23
WO2003063555A1 (en) 2003-07-31
CN1520702A (zh) 2004-08-11
KR100879695B1 (ko) 2009-01-21
IL158314A0 (en) 2004-05-12
CN1520702B (zh) 2010-05-26

Similar Documents

Publication Publication Date Title
US6670645B2 (en) Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
US6946688B2 (en) Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
JP4299144B2 (ja) フッ素化フェニルピリジン、フェニルピリミジン、およびフェニルキノリンを含むエレクトロルミネッセンスイリジウム化合物ならびにこのような化合物を用いて製造されるデバイス
AU2001271550B2 (en) Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
AU2001271550A1 (en) Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
US7132681B2 (en) Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
KR100871275B1 (ko) 불소화 페닐피리딘과 이리듐의 전기발광 화합물 및 이 화합물로 제조된 장치
AU2002231155A1 (en) Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
KR20080081209A (ko) 불소화 페닐피리딘 화합물

Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued