JP5345519B2 - ヘテロレプティックな遷移金属−カルベン錯体及びそれを有機発光ダイオード(oled)において用いる使用 - Google Patents

ヘテロレプティックな遷移金属−カルベン錯体及びそれを有機発光ダイオード(oled)において用いる使用 Download PDF

Info

Publication number
JP5345519B2
JP5345519B2 JP2009503568A JP2009503568A JP5345519B2 JP 5345519 B2 JP5345519 B2 JP 5345519B2 JP 2009503568 A JP2009503568 A JP 2009503568A JP 2009503568 A JP2009503568 A JP 2009503568A JP 5345519 B2 JP5345519 B2 JP 5345519B2
Authority
JP
Japan
Prior art keywords
group
groups
carbene
heteroaryl
alkyl
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.)
Active
Application number
JP2009503568A
Other languages
English (en)
Japanese (ja)
Other versions
JP2009532431A (ja
JP2009532431A5 (enExample
Inventor
フックス エヴェリン
エーゲン マルティーナ
カーレ クラウス
レナルツ クリスティアン
モルト オリヴァー
ノルト ジーモン
コヴァルスキー ヴォルフガング
シルトクネヒト クリスティアン
ヨハネス ハンス−ヘルマン
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of JP2009532431A publication Critical patent/JP2009532431A/ja
Publication of JP2009532431A5 publication Critical patent/JP2009532431A5/ja
Application granted granted Critical
Publication of JP5345519B2 publication Critical patent/JP5345519B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/06Cobalt compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033Iridium compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/02Iron compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04Nickel compounds
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05BELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00Electroluminescent light sources
    • H05B33/12Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14Light 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
    • 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
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1007Non-condensed systems
    • 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
    • C09K2211/1044Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1059Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • 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
    • H10K85/60Organic compounds having low molecular weight
    • 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
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/631Amine 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)
JP2009503568A 2006-04-05 2007-04-03 ヘテロレプティックな遷移金属−カルベン錯体及びそれを有機発光ダイオード(oled)において用いる使用 Active JP5345519B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP06112228.9 2006-04-05
EP06112228 2006-04-05
PCT/EP2007/053213 WO2007115970A1 (de) 2006-04-05 2007-04-03 Heteroleptische übergangsmetall-carben-komplexe und deren verwendung in organischen leuchtdioden (oleds)

Publications (3)

Publication Number Publication Date
JP2009532431A JP2009532431A (ja) 2009-09-10
JP2009532431A5 JP2009532431A5 (enExample) 2012-10-25
JP5345519B2 true JP5345519B2 (ja) 2013-11-20

Family

ID=38016687

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2009503568A Active JP5345519B2 (ja) 2006-04-05 2007-04-03 ヘテロレプティックな遷移金属−カルベン錯体及びそれを有機発光ダイオード(oled)において用いる使用

Country Status (7)

Country Link
US (2) US10385263B2 (enExample)
EP (1) EP2007779B1 (enExample)
JP (1) JP5345519B2 (enExample)
KR (1) KR101431844B1 (enExample)
CN (1) CN101460515B (enExample)
AT (1) ATE550342T1 (enExample)
WO (1) WO2007115970A1 (enExample)

Families Citing this family (165)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004057072A1 (de) * 2004-11-25 2006-06-01 Basf Ag Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs)
WO2008132085A1 (de) * 2007-04-26 2008-11-06 Basf Se Silane enthaltend phenothiazin-s-oxid oder phenothiazin-s,s-dioxid-gruppen und deren verwendung in oleds
EP2165377B1 (de) * 2007-07-05 2021-04-28 UDC Ireland Limited Organische leuchtdioden enthaltend carben-übergangsmetall-komplex-emitter und mindestens eine verbindung ausgewählt aus disilylcarbazolen; disilyldibenzofuranen, disilyldibenzothiophenen, disilyldibenzophospholen, disilyldibenzothiophen-s-oxiden und disilyldibenzothiophen-s,s-dioxiden
EP3345983B1 (de) 2007-07-05 2020-08-26 UDC Ireland Limited Verbindungen enthaltend mindestens eine disilylverbindung ausgewählt aus disilylcarbazolen, disilyldibenzofuranen, disilyldibenzothiophenen, disilyldibenzophospholen, disilyldibenzothiophen-s-oxiden und disilyldibenzothiophen-s, s-dioxiden
ATE519770T1 (de) * 2007-10-17 2011-08-15 Basf Se Übergangsmetallkomplexe mit verbrückten carbenliganden und deren verwendung in oleds
EP2297800B1 (de) 2008-06-10 2019-08-14 UDC Ireland Limited Deuterierte übergangsmetall- komplexe und deren verwendung in organischen leuchtdioden
US8377332B2 (en) 2008-06-10 2013-02-19 Basf Se Transition metal complexes and use thereof in organic light emitting diodes—III
JP5780956B2 (ja) 2008-06-20 2015-09-16 ビーエーエスエフ ソシエタス・ヨーロピアBasf Se 環状ホスファゼン化合物及び有機発光ダイオード中でのその使用
DE102008033563A1 (de) 2008-07-17 2010-01-21 Merck Patent Gmbh Komplexe mit kleinen Singulett-Triplett-Energie-Abständen zur Verwendung in opto-elektronischen Bauteilen (Singulett-Harvesting-Effekt)
KR101761236B1 (ko) 2008-10-07 2017-07-25 오스람 오엘이디 게엠베하 축합환계로 치환된 실롤 및 유기전자소자에서의 그 용도
EP2401254B1 (de) 2009-02-26 2013-06-19 Novaled AG Chinonverbindungen als dotierstoff in der organischen elektronik
US9029804B2 (en) * 2009-10-19 2015-05-12 University Of Mississippi Air-stable, blue light emitting chemical compounds
KR101986469B1 (ko) 2009-10-28 2019-06-05 유디씨 아일랜드 리미티드 이종 리간드 카르벤 착체 및 유기 전자장치에서의 이의 용도
WO2011073149A1 (de) 2009-12-14 2011-06-23 Basf Se Metallkomplexe, enthaltend diazabenzimidazolcarben-liganden und deren verwendung in oleds
US8691401B2 (en) 2010-04-16 2014-04-08 Basf Se Bridged benzimidazole-carbene complexes and use thereof in OLEDS
EP2582769B1 (en) 2010-06-18 2014-11-19 Basf Se Organic electronic devices comprising a layer of a dibenzofurane compound and a 8-hydroxyquinolinolato earth alkaline metal, or alkali metal complex
US9142792B2 (en) 2010-06-18 2015-09-22 Basf Se Organic electronic devices comprising a layer comprising at least one metal organic compound and at least one metal oxide
CN102947415B (zh) * 2010-06-18 2016-01-06 巴斯夫欧洲公司 包含吡啶化合物和8-羟基喹啉根合碱土金属或碱金属配合物的层的有机电子器件
MX344784B (es) 2010-09-29 2017-01-06 Basf Se Elemento de seguridad.
CN103153974A (zh) 2010-10-07 2013-06-12 巴斯夫欧洲公司 用于电子应用的菲并[9,10-b]呋喃
US9079872B2 (en) 2010-10-07 2015-07-14 Basf Se Phenanthro[9, 10-B]furans for electronic applications
WO2012080052A1 (en) 2010-12-13 2012-06-21 Basf Se Bispyrimidines for electronic applications
US8362246B2 (en) 2010-12-13 2013-01-29 Basf Se Bispyrimidines for electronic applications
US8883322B2 (en) 2011-03-08 2014-11-11 Universal Display Corporation Pyridyl carbene phosphorescent emitters
US9806270B2 (en) 2011-03-25 2017-10-31 Udc Ireland Limited 4H-imidazo[1,2-a]imidazoles for electronic applications
CN106188065B (zh) 2011-03-25 2021-12-28 Udc 爱尔兰有限责任公司 用于电子应用的4H-咪唑并[1,2-a]咪唑
KR102166396B1 (ko) * 2011-06-08 2020-10-16 유니버셜 디스플레이 코포레이션 헤테로렙틱 이리듐 카르벤 착물 및 이를 사용한 발광 디바이스
US9315724B2 (en) 2011-06-14 2016-04-19 Basf Se Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs
EP3415521A1 (en) 2011-06-14 2018-12-19 UDC Ireland Limited Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in oleds
CN103917542B (zh) 2011-11-10 2018-03-27 Udc 爱尔兰有限责任公司 用于电子应用的4H‑咪唑并[1,2‑a]咪唑
EP2802594B1 (en) 2012-01-12 2017-04-19 UDC Ireland Limited Metal complexes with dibenzo[f,h]quinoxalines
US9502672B2 (en) * 2012-06-21 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
WO2014009317A1 (en) 2012-07-10 2014-01-16 Basf Se Benzimidazo[1,2-a]benzimidazole derivatives for electronic applications
US9590196B2 (en) 2012-07-19 2017-03-07 Udc Ireland Limited Dinuclear metal complexes comprising carbene ligands and the use thereof in OLEDs
CN104662023B (zh) 2012-09-20 2017-08-18 Udc 爱尔兰有限责任公司 供电子应用的氮杂二苯并呋喃
TWI597285B (zh) 2012-11-06 2017-09-01 Udc愛爾蘭責任有限公司 用於電子應用之以啡噁矽(phenoxasiline)為基之化合物
CN105051927B (zh) 2013-03-20 2020-10-16 Udc 爱尔兰有限责任公司 在oled中用作效率促进剂的氮杂苯并咪唑卡宾配体
JP6285538B2 (ja) 2013-04-29 2018-02-28 ユー・ディー・シー アイルランド リミテッド カルベン配位子を有する遷移金属錯体及びそれらをoledに用いる使用
KR102464739B1 (ko) 2013-07-02 2022-11-09 유디씨 아일랜드 리미티드 유기 발광 다이오드에 사용하기 위한 일치환된 디아자벤즈이미다졸 카르벤 금속 착체
US20150028290A1 (en) * 2013-07-25 2015-01-29 Universal Display Corporation Heteroleptic osmium complex and method of making the same
CN109021022B (zh) 2013-07-31 2021-04-16 Udc 爱尔兰有限责任公司 发光的二氮杂苯并咪唑碳烯金属配合物
WO2015063046A1 (en) 2013-10-31 2015-05-07 Basf Se Azadibenzothiophenes for electronic applications
US9905784B2 (en) 2013-11-15 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
KR102491669B1 (ko) 2013-12-20 2023-01-26 유디씨 아일랜드 리미티드 매우 짧은 감쇠 시간을 갖는 고효율 oled 장치
EP3126371B1 (en) 2014-03-31 2021-11-10 UDC Ireland Limited Metal complexes, comprising carbene ligands having an o-substituted non-cyclometalated aryl group and their use in organic light emitting diodes
EP3174885B1 (en) 2014-07-28 2019-10-02 Idemitsu Kosan Co., Ltd. 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds)
EP2982676B1 (en) 2014-08-07 2018-04-11 Idemitsu Kosan Co., Ltd. Benzimidazo[2,1-B]benzoxazoles for electronic applications
CN107074896B (zh) 2014-08-08 2021-04-13 Udc 爱尔兰有限责任公司 电致发光咪唑并喹喔啉碳烯金属络合物
EP2993215B1 (en) 2014-09-04 2019-06-19 Idemitsu Kosan Co., Ltd. Azabenzimidazo[2,1-a]benzimidazoles for electronic applications
EP3015469B1 (en) 2014-10-30 2018-12-19 Idemitsu Kosan Co., Ltd. 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications
WO2016079667A1 (en) 2014-11-17 2016-05-26 Idemitsu Kosan Co., Ltd. Indole derivatives for electronic applications
US10424746B2 (en) 2014-11-18 2019-09-24 Udc Ireland Limited Pt- or Pd-carbene complexes for use in organic light emitting diodes
EP3034507A1 (en) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs)
EP3034506A1 (en) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd 4-functionalized carbazole derivatives for electronic applications
EP3054498B1 (en) 2015-02-06 2017-09-20 Idemitsu Kosan Co., Ltd. Bisimidazodiazocines
EP3053918B1 (en) 2015-02-06 2018-04-11 Idemitsu Kosan Co., Ltd. 2-carbazole substituted benzimidazoles for electronic applications
DE102015101767A1 (de) 2015-02-06 2016-08-11 Technische Universität Dresden Blaue Fluoreszenzemitter
US9929361B2 (en) 2015-02-16 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
EP3061759B1 (en) 2015-02-24 2019-12-25 Idemitsu Kosan Co., Ltd Nitrile substituted dibenzofurans
US11056657B2 (en) 2015-02-27 2021-07-06 University Display Corporation Organic electroluminescent materials and devices
EP3070144B1 (en) 2015-03-17 2018-02-28 Idemitsu Kosan Co., Ltd. Seven-membered ring compounds
EP3072943B1 (en) 2015-03-26 2018-05-02 Idemitsu Kosan Co., Ltd. Dibenzofuran/carbazole-substituted benzonitriles
EP3075737B1 (en) 2015-03-31 2019-12-04 Idemitsu Kosan Co., Ltd Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes
US9859510B2 (en) 2015-05-15 2018-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US10418568B2 (en) 2015-06-01 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
KR102471707B1 (ko) 2015-06-03 2022-11-29 유디씨 아일랜드 리미티드 매우 짧은 붕괴 시간을 갖는 고효율 oled 소자
US11127905B2 (en) 2015-07-29 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US10672996B2 (en) 2015-09-03 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
WO2017056055A1 (en) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes
EP3150606B1 (en) 2015-10-01 2019-08-14 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes
EP3150604B1 (en) 2015-10-01 2021-07-14 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes
KR20180079328A (ko) 2015-11-04 2018-07-10 이데미쓰 고산 가부시키가이샤 벤즈이미다졸 축합 헤테로아릴
WO2017093958A1 (en) 2015-12-04 2017-06-08 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes
KR102684614B1 (ko) 2015-12-21 2024-07-15 유디씨 아일랜드 리미티드 삼각형 리간드를 갖는 전이 금속 착체 및 oled에서의 이의 용도
CN108699058B (zh) 2015-12-21 2022-07-08 出光兴产株式会社 杂稠合苯基喹唑啉类和它们在电子器件中的用途
DE102015122869A1 (de) 2015-12-28 2017-06-29 Technische Universität Dresden Neue Emittermaterialien und Matrixmaterialien für optoelektronische und elektronische Bauelemente, insbesondere organische lichtemittierende Dioden (OLEDs)
US20170229663A1 (en) 2016-02-09 2017-08-10 Universal Display Corporation Organic electroluminescent materials and devices
US10236456B2 (en) 2016-04-11 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
WO2017178864A1 (en) 2016-04-12 2017-10-19 Idemitsu Kosan Co., Ltd. Seven-membered ring compounds
DE102016110970A1 (de) 2016-06-15 2017-12-21 Technische Universität Dresden Effiziente lichtemittierende Emittermoleküle für optoelektronische Anwendungen durch gezielte Verstärkung der Emission aus ladungsseparierten CT-Zuständen auf Basis dual fluoreszierender Benzol-(Poly)carboxylat-Akzeptoren
US10862054B2 (en) 2016-06-20 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US11482683B2 (en) 2016-06-20 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US10672997B2 (en) 2016-06-20 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
KR102447668B1 (ko) 2016-06-22 2022-09-26 이데미쓰 고산 가부시키가이샤 유기 발광 다이오드를 위한 특이적으로 치환된 벤조푸로- 및 벤조티에노퀴놀린
US10608186B2 (en) 2016-09-14 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US10680187B2 (en) 2016-09-23 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US11196010B2 (en) 2016-10-03 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices
US11011709B2 (en) 2016-10-07 2021-05-18 Universal Display Corporation Organic electroluminescent materials and devices
US12317745B2 (en) 2016-11-09 2025-05-27 Universal Display Corporation Organic electroluminescent materials and devices
US10680188B2 (en) 2016-11-11 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US11780865B2 (en) 2017-01-09 2023-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US10844085B2 (en) 2017-03-29 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US10944060B2 (en) 2017-05-11 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
EP3418285B1 (en) 2017-06-20 2020-05-06 Idemitsu Kosan Co., Ltd. Composition comprising a substituted ir complex and a phenylquinazoline bridged with a heteroatom
US12098157B2 (en) 2017-06-23 2024-09-24 Universal Display Corporation Organic electroluminescent materials and devices
US11228010B2 (en) 2017-07-26 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
KR102456073B1 (ko) * 2017-07-28 2022-10-19 삼성디스플레이 주식회사 유기금속 화합물 및 이를 포함한 유기 발광 소자
US11744142B2 (en) 2017-08-10 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
KR102504132B1 (ko) 2017-08-21 2023-02-28 삼성디스플레이 주식회사 유기금속 화합물, 이를 포함한 유기 발광 소자 및 상기 유기 발광 소자를 포함한 발광 장치
EP3466954A1 (en) 2017-10-04 2019-04-10 Idemitsu Kosan Co., Ltd. Fused phenylquinazolines bridged with a heteroatom
US12180230B2 (en) 2017-11-28 2024-12-31 University Of Southern California Carbene compounds and organic electroluminescent devices
EP3492480B1 (en) 2017-11-29 2021-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US11937503B2 (en) 2017-11-30 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11542289B2 (en) 2018-01-26 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US11165028B2 (en) 2018-03-12 2021-11-02 Universal Display Corporation Organic electroluminescent materials and devices
EP3604477A1 (en) 2018-07-30 2020-02-05 Idemitsu Kosan Co., Ltd. Polycyclic compound, organic electroluminescence device, and electronic device
EP3608319A1 (en) 2018-08-07 2020-02-12 Idemitsu Kosan Co., Ltd. Condensed aza cycles as organic light emitting device and materials for use in same
US12453279B2 (en) 2018-08-22 2025-10-21 Universal Display Corporation Organic electroluminescent materials and devices
KR102769406B1 (ko) 2018-09-12 2025-02-17 메르크 파텐트 게엠베하 유기 전계발광 디바이스용 재료
TW202030902A (zh) 2018-09-12 2020-08-16 德商麥克專利有限公司 電致發光裝置
TWI826522B (zh) 2018-09-12 2023-12-21 德商麥克專利有限公司 電致發光裝置
US11737349B2 (en) 2018-12-12 2023-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US11780829B2 (en) 2019-01-30 2023-10-10 The University Of Southern California Organic electroluminescent materials and devices
US12477890B2 (en) 2019-02-01 2025-11-18 Universal Display Corporation Organic electroluminescent materials and devices
US20220127286A1 (en) 2019-03-04 2022-04-28 Merck Patent Gmbh Ligands for nano-sized materials
JP2020158491A (ja) 2019-03-26 2020-10-01 ユニバーサル ディスプレイ コーポレイション 有機エレクトロルミネセンス材料及びデバイス
EP3935063A1 (en) 2019-04-11 2022-01-12 Merck Patent GmbH Materials for organic electroluminescent devices
US12281128B2 (en) 2019-07-30 2025-04-22 Universal Display Corporation Organic electroluminescent materials and devices
US12139501B2 (en) 2019-08-16 2024-11-12 Universal Display Corporation Organic electroluminescent materials and devices
US20210135130A1 (en) 2019-11-04 2021-05-06 Universal Display Corporation Organic electroluminescent materials and devices
WO2021089450A1 (en) 2019-11-04 2021-05-14 Merck Patent Gmbh Materials for organic electroluminescent devices
TW202134252A (zh) 2019-11-12 2021-09-16 德商麥克專利有限公司 有機電致發光裝置用材料
TW202136181A (zh) 2019-12-04 2021-10-01 德商麥克專利有限公司 有機電致發光裝置用的材料
US20210217969A1 (en) 2020-01-06 2021-07-15 Universal Display Corporation Organic electroluminescent materials and devices
US12426495B2 (en) 2020-01-28 2025-09-23 Universal Display Corporation Organic electroluminescent materials and devices
EP4097090A1 (de) 2020-01-29 2022-12-07 Merck Patent GmbH Benzimidazol-derivate
US20230337537A1 (en) 2020-03-23 2023-10-19 Merck Patent Gmbh Materials for organic electroluminescent devices
EP3937268B1 (en) 2020-07-10 2025-05-07 Universal Display Corporation Plasmonic oleds and vertical dipole emitters
US12187748B2 (en) 2020-11-02 2025-01-07 Universal Display Corporation Organic electroluminescent materials and devices
US20220158096A1 (en) 2020-11-16 2022-05-19 Universal Display Corporation Organic electroluminescent materials and devices
US12325717B2 (en) 2020-11-24 2025-06-10 Universal Display Corporation Organic electroluminescent materials and devices
US20220165967A1 (en) 2020-11-24 2022-05-26 Universal Display Corporation Organic electroluminescent materials and devices
US20220271241A1 (en) 2021-02-03 2022-08-25 Universal Display Corporation Organic electroluminescent materials and devices
EP4059915B1 (en) 2021-02-26 2025-12-24 Universal Display Corporation Organic electroluminescent materials and devices
EP4060758A3 (en) 2021-02-26 2023-03-29 Universal Display Corporation Organic electroluminescent materials and devices
US20220298192A1 (en) 2021-03-05 2022-09-22 Universal Display Corporation Organic electroluminescent materials and devices
US12428599B2 (en) 2021-03-09 2025-09-30 Universal Display Corporation Organic electroluminescent materials and devices
US20220298190A1 (en) 2021-03-12 2022-09-22 Universal Display Corporation Organic electroluminescent materials and devices
US12421262B2 (en) 2021-03-15 2025-09-23 Universal Display Corporation Organic electroluminescent materials and devices
US20220340607A1 (en) 2021-04-05 2022-10-27 Universal Display Corporation Organic electroluminescent materials and devices
US12480042B2 (en) 2021-04-09 2025-11-25 Universal Display Corporation Organic electroluminescent materials and devices
EP4075531A1 (en) 2021-04-13 2022-10-19 Universal Display Corporation Plasmonic oleds and vertical dipole emitters
US20220352478A1 (en) 2021-04-14 2022-11-03 Universal Display Corporation Organic eletroluminescent materials and devices
US20230006149A1 (en) 2021-04-23 2023-01-05 Universal Display Corporation Organic electroluminescent materials and devices
US20220407020A1 (en) 2021-04-23 2022-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US20230133787A1 (en) 2021-06-08 2023-05-04 University Of Southern California Molecular Alignment of Homoleptic Iridium Phosphors
EP4151699A1 (en) 2021-09-17 2023-03-22 Universal Display Corporation Organic electroluminescent materials and devices
US12473318B2 (en) 2021-10-08 2025-11-18 Universal Display Corporation Organic electroluminescent materials and devices
US12509628B2 (en) 2021-12-16 2025-12-30 Universal Display Corporation Organic electroluminescent materials and devices
EP4231804A3 (en) 2022-02-16 2023-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US20230292592A1 (en) 2022-03-09 2023-09-14 Universal Display Corporation Organic electroluminescent materials and devices
US20230337516A1 (en) 2022-04-18 2023-10-19 Universal Display Corporation Organic electroluminescent materials and devices
US20230389421A1 (en) 2022-05-24 2023-11-30 Universal Display Corporation Organic electroluminescent materials and devices
EP4293001A1 (en) 2022-06-08 2023-12-20 Universal Display Corporation Organic electroluminescent materials and devices
US20240016051A1 (en) 2022-06-28 2024-01-11 Universal Display Corporation Organic electroluminescent materials and devices
US20240107880A1 (en) 2022-08-17 2024-03-28 Universal Display Corporation Organic electroluminescent materials and devices
US20240196730A1 (en) 2022-10-27 2024-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US20240188319A1 (en) 2022-10-27 2024-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US20240180025A1 (en) 2022-10-27 2024-05-30 Universal Display Corporation Organic electroluminescent materials and devices
US20240188316A1 (en) 2022-10-27 2024-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US20240188419A1 (en) 2022-10-27 2024-06-06 Universal Display Corporation Organic electroluminescent materials and devices
WO2024105066A1 (en) 2022-11-17 2024-05-23 Merck Patent Gmbh Materials for organic electroluminescent devices
US20240247017A1 (en) 2022-12-14 2024-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US20250204238A1 (en) 2023-12-15 2025-06-19 Universal Display Corporation Organic electroluminscent materials and devices
US20250204239A1 (en) 2023-12-15 2025-06-19 Universal Display Corporation Organic electroluminescent materials and devices

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10104426A1 (de) 2001-02-01 2002-08-08 Covion Organic Semiconductors Verfahren zur Herstellung von hochreinen, tris-ortho-metallierten Organo-Iridium-Verbindungen
DE10338550A1 (de) 2003-08-19 2005-03-31 Basf Ag Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs)
WO2005113704A2 (en) * 2004-05-18 2005-12-01 The University Of Southern California Luminescent compounds with carbene ligands
US7601436B2 (en) * 2004-05-18 2009-10-13 The University Of Southern California Carbene metal complexes as OLED materials
DE102004040005A1 (de) 2004-08-18 2006-02-23 Basf Ag In Polymermatrices eingebettete Übergangsmetallcarbenkomplexe zur Verwendung in OLEDs
DE102004057072A1 (de) * 2004-11-25 2006-06-01 Basf Ag Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs)
DE102005014284A1 (de) * 2005-03-24 2006-09-28 Basf Ag Verwendung von Verbindungen, welche aromatische oder heteroaromatische über Carbonyl-Gruppen enthaltende Gruppen verbundene Ringe enthalten, als Matrixmaterialien in organischen Leuchtdioden
ATE519770T1 (de) 2007-10-17 2011-08-15 Basf Se Übergangsmetallkomplexe mit verbrückten carbenliganden und deren verwendung in oleds

Also Published As

Publication number Publication date
ATE550342T1 (de) 2012-04-15
EP2007779B1 (de) 2012-03-21
CN101460515A (zh) 2009-06-17
KR20090005349A (ko) 2009-01-13
US20090096367A1 (en) 2009-04-16
KR101431844B1 (ko) 2014-08-25
CN101460515B (zh) 2013-05-15
US20190322929A1 (en) 2019-10-24
US11692131B2 (en) 2023-07-04
EP2007779A1 (de) 2008-12-31
JP2009532431A (ja) 2009-09-10
US10385263B2 (en) 2019-08-20
WO2007115970A1 (de) 2007-10-18

Similar Documents

Publication Publication Date Title
JP5345519B2 (ja) ヘテロレプティックな遷移金属−カルベン錯体及びそれを有機発光ダイオード(oled)において用いる使用
JP5615178B2 (ja) 架橋カルベンリガンドを有する遷移金属錯体およびoledにおけるその使用
JP2009532549A (ja) 1つの非カルベン配位子と1もしくは2つのカルベン配位子を有する遷移金属錯体並びにoledにおけるその使用
KR101642030B1 (ko) 가교된 카르벤 리간드를 포함하는 전이 금속 착물 및 이의 용도
JP4351702B2 (ja) 有機発光ダイオード用の発光体としてカルベンリガンドを有する遷移金属錯体
JP5001851B2 (ja) 有機発光ダイオード(oled)における遷移金属−カルベン錯体の使用
JP5165854B2 (ja) シリル置換シクロメタル化遷移金属錯体およびこれを用いた有機電界発光素子
KR101656793B1 (ko) 신규한 전이 금속 착물 및 이의 유기 발광 다이오드에서의 용도 - ⅲ
JP2011524869A (ja) 重水素化された遷移金属錯体及びそれを有機発光ダイオードにおいて用いる使用−v
KR20120101651A (ko) 복핵 백금-카르벤 착체 및 oled에서의 이의 용도
JP2011523955A (ja) 新規の遷移金属錯体及びそれを有機発光ダイオードにおいて用いる使用−iv

Legal Events

Date Code Title Description
RD04 Notification of resignation of power of attorney

Free format text: JAPANESE INTERMEDIATE CODE: A7424

Effective date: 20101227

Free format text: JAPANESE INTERMEDIATE CODE: A7424

Effective date: 20101228

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20110831

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20110902

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20111124

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20111201

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20111220

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20111228

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20120314

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20120611

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20120618

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20120712

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20120720

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20120814

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20120821

A524 Written submission of copy of amendment under article 19 pct

Free format text: JAPANESE INTERMEDIATE CODE: A524

Effective date: 20120907

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20130125

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20130422

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20130430

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20130527

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20130603

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20130621

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20130716

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20130814

R150 Certificate of patent or registration of utility model

Ref document number: 5345519

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

S111 Request for change of ownership or part of ownership

Free format text: JAPANESE INTERMEDIATE CODE: R313113

R350 Written notification of registration of transfer

Free format text: JAPANESE INTERMEDIATE CODE: R350

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250