JP6557002B2 - ５，６−ジアリール−２−ピラジルトリフラート、トリアリールピラジン誘導体の合成方法、および有機金属錯体の合成方法 - Google Patents

５，６−ジアリール−２−ピラジルトリフラート、トリアリールピラジン誘導体の合成方法、および有機金属錯体の合成方法 Download PDF

Info

Publication number
JP6557002B2
JP6557002B2 JP2014238749A JP2014238749A JP6557002B2 JP 6557002 B2 JP6557002 B2 JP 6557002B2 JP 2014238749 A JP2014238749 A JP 2014238749A JP 2014238749 A JP2014238749 A JP 2014238749A JP 6557002 B2 JP6557002 B2 JP 6557002B2
Authority
JP
Japan
Prior art keywords
light
abbreviation
layer
bis
synthesis
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
JP2014238749A
Other languages
English (en)
Japanese (ja)
Other versions
JP2015127321A5 (enExample
JP2015127321A (ja
Inventor
英子 井上
英子 井上
朋広 久保田
朋広 久保田
美樹 金元
美樹 金元
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.)
Semiconductor Energy Laboratory Co Ltd
Original Assignee
Semiconductor Energy Laboratory Co Ltd
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 Semiconductor Energy Laboratory Co Ltd filed Critical Semiconductor Energy Laboratory Co Ltd
Priority to JP2014238749A priority Critical patent/JP6557002B2/ja
Publication of JP2015127321A publication Critical patent/JP2015127321A/ja
Publication of JP2015127321A5 publication Critical patent/JP2015127321A5/ja
Application granted granted Critical
Publication of JP6557002B2 publication Critical patent/JP6557002B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D241/18—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
    • 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
    • C09K2211/18—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
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • 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

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)
JP2014238749A 2013-11-28 2014-11-26 ５，６−ジアリール−２−ピラジルトリフラート、トリアリールピラジン誘導体の合成方法、および有機金属錯体の合成方法 Active JP6557002B2 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2014238749A JP6557002B2 (ja) 2013-11-28 2014-11-26 ５，６−ジアリール−２−ピラジルトリフラート、トリアリールピラジン誘導体の合成方法、および有機金属錯体の合成方法

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2013245957 2013-11-28
JP2013245957 2013-11-28
JP2014238749A JP6557002B2 (ja) 2013-11-28 2014-11-26 ５，６−ジアリール−２−ピラジルトリフラート、トリアリールピラジン誘導体の合成方法、および有機金属錯体の合成方法

Publications (3)

Publication Number Publication Date
JP2015127321A JP2015127321A (ja) 2015-07-09
JP2015127321A5 JP2015127321A5 (enExample) 2017-12-28
JP6557002B2 true JP6557002B2 (ja) 2019-08-07

Family

ID=53183003

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2014238749A Active JP6557002B2 (ja) 2013-11-28 2014-11-26 ５，６−ジアリール−２−ピラジルトリフラート、トリアリールピラジン誘導体の合成方法、および有機金属錯体の合成方法

Country Status (3)

Country Link
US (2) US9231217B2 (enExample)
JP (1) JP6557002B2 (enExample)
CN (1) CN104672152B (enExample)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9231217B2 (en) * 2013-11-28 2016-01-05 Semiconductor Energy Laboratory Co., Ltd. Synthesis method of organometallic complex, synthesis method of pyrazine derivative, 5,6-diaryl-2-pyrazyl triflate, light-emitting element, light-emitting device, electronic device, and lighting device
US10854826B2 (en) * 2014-10-08 2020-12-01 Universal Display Corporation Organic electroluminescent compounds, compositions and devices
US10153449B2 (en) 2014-10-16 2018-12-11 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
US10074822B2 (en) 2014-10-28 2018-09-11 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device

Family Cites Families (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4303689A (en) * 1965-04-30 1981-12-01 Firmenich Sa Flavoring with pyrazine derivatives
AUPO903897A0 (en) * 1997-09-08 1997-10-02 Commonwealth Scientific And Industrial Research Organisation Organic boronic acid derivatives
US6017944A (en) * 1997-10-28 2000-01-25 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
ES2183532T3 (es) * 1998-03-18 2003-03-16 Ciba Sc Holding Ag Reacciones de copulacion con catalizadores de paladio.
US6395916B1 (en) * 1998-07-10 2002-05-28 Massachusetts Institute Of Technology Ligands for metals and improved metal-catalyzed processes based thereon
US7223879B2 (en) * 1998-07-10 2007-05-29 Massachusetts Institute Of Technology Ligands for metals and improved metal-catalyzed processes based thereon
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
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
US6794529B2 (en) * 2000-07-07 2004-09-21 Commonwealth Scientific And Industrial Research Organisation Substituted diboron compounds
JP4154139B2 (ja) * 2000-09-26 2008-09-24 キヤノン株式会社 発光素子
CN100505376C (zh) 2000-11-30 2009-06-24 佳能株式会社 发光器件和显示装置
US7202367B2 (en) * 2002-05-31 2007-04-10 Rhodia Chimie Process for arylating or vinylating or alkynating a nucleophilic compound
DE10238903A1 (de) * 2002-08-24 2004-03-04 Covion Organic Semiconductors Gmbh Rhodium- und Iridium-Komplexe
DE10249926A1 (de) * 2002-10-26 2004-05-06 Covion Organic Semiconductors Gmbh Rhodium- und Iridium-Komplexe
KR101206449B1 (ko) * 2003-12-02 2012-11-29 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자
US8895154B2 (en) 2004-03-02 2014-11-25 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
US8084145B2 (en) * 2004-04-02 2011-12-27 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light emitting element using the complex, light emitting device using the element, and electric apparatus using the device
CN100482024C (zh) * 2004-05-20 2009-04-22 株式会社半导体能源研究所 发光元件及发光装置
US7771844B2 (en) * 2004-12-03 2010-08-10 Semiconductor Energy Laboratory Co., Ltd Organic metal complex and photoelectronic device, light-emitting element and light-emitting device using the same
KR101318125B1 (ko) 2005-03-17 2013-10-16 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기금속 착체 및 이를 사용하는 발광 소자, 발광 장치 및 전자 장치
WO2006104177A1 (en) * 2005-03-28 2006-10-05 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, and light-emitting device and electronic appliance using the same
KR101363278B1 (ko) * 2005-06-27 2014-02-21 엑셀리시스 페이턴트 컴퍼니 엘엘씨 이미다졸계 ｌｘｒ 변조제
US20070128658A1 (en) * 2005-11-14 2007-06-07 Blackwell Helen E Fluorescent dyes, methods and uses thereof
CN104497054B (zh) * 2005-12-05 2017-09-22 株式会社半导体能源研究所 有机金属配合物和使用它的发光元件、发光设备和电子设备
TWI481616B (zh) * 2006-03-21 2015-04-21 Semiconductor Energy Lab 有機金屬錯合物及使用該有機金屬錯合物之發光元件，發光裝置和電子裝置
KR101324155B1 (ko) * 2007-05-18 2013-11-01 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기금속 착체
EP2238128B1 (en) * 2007-12-26 2012-08-22 Sanofi Heterocyclic pyrazole-carboxamides as p2y12 antagonists
EP2238127B1 (en) * 2007-12-26 2012-08-15 Sanofi Pyrazole-carboxamide derivatives as p2y12 antagonists
JP5271721B2 (ja) * 2008-01-23 2013-08-21 株式会社半導体エネルギー研究所 トリアリールピラジン誘導体の製造方法
US8207169B2 (en) * 2008-06-03 2012-06-26 Msd K.K. Substituted [1,2,4]triazolo[4′,3′:1,6]pyrido[2,3-b]pyrazines of the formula D
EP2303897A4 (en) * 2008-06-05 2012-02-22 Harvard College HIGH VALENCIA PALLADIUM FLUORIDE COMPLEXES AND USES THEREOF
US8101755B2 (en) 2008-10-23 2012-01-24 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex including pyrazine derivative
EP2196518B1 (en) * 2008-11-17 2018-09-26 Semiconductor Energy Laboratory Co., Ltd. Light-Emitting Element and Light-Emitting Device
DE102009005746A1 (de) * 2009-01-23 2010-07-29 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009030848A1 (de) * 2009-06-26 2011-02-03 Merck Patent Gmbh Polymere enthaltend Struktureinheiten, die Alkylalkoxygruppen aufweisen, Blends enthaltend diese Polymere sowie optoelektronische Vorrichtungen enthaltend diese Polymere und Blends
DE102010009193B4 (de) * 2010-02-24 2022-05-19 MERCK Patent Gesellschaft mit beschränkter Haftung Zusammensetzung enthaltend Fluor-Fluor Assoziate, Verfahren zu deren Herstellung, deren Verwendung sowie organische elektronische Vorrichtung diese enthaltend
JP5602555B2 (ja) * 2010-05-17 2014-10-08 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器及び照明装置
DE102010048608A1 (de) * 2010-10-15 2012-04-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
US8664383B2 (en) * 2010-10-15 2014-03-04 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, and light-emitting element and display device using the organometallic complex
JP5799772B2 (ja) * 2010-11-25 2015-10-28 Jnc株式会社 電子輸送材料およびこれを用いた有機電界発光素子
DE102010055901A1 (de) * 2010-12-23 2012-06-28 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102010056151A1 (de) * 2010-12-28 2012-06-28 Merck Patent Gmbh Materiallen für organische Elektrolumineszenzvorrichtungen
EP2669262B1 (en) * 2011-01-27 2018-03-07 JNC Corporation Novel anthracene compound and organic electroluminescence element using same
JP5206907B2 (ja) * 2011-04-07 2013-06-12 三菱化学株式会社 有機化合物、電荷輸送材料、該化合物を含有する組成物、有機電界発光素子、表示装置及び照明装置
DE102011104745A1 (de) * 2011-06-17 2012-12-20 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
US9260463B2 (en) 2011-11-30 2016-02-16 Semiconductor Energy Laboratory Co., Ltd. Substituted pyrimidinato iridium complexes and substituted pyrazinato iridium complexes having an alicyclic diketone ligand
TWI490211B (zh) 2011-12-23 2015-07-01 Semiconductor Energy Lab 有機金屬錯合物，發光元件，發光裝置，電子裝置及照明裝置
JP6136311B2 (ja) * 2012-02-06 2017-05-31 Jnc株式会社 電子輸送材料およびこれを用いた有機電界発光素子
JP6166557B2 (ja) * 2012-04-20 2017-07-19 株式会社半導体エネルギー研究所 燐光性有機金属イリジウム錯体、発光素子、発光装置、電子機器、および照明装置
US8921549B2 (en) * 2012-06-01 2014-12-30 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
US20140014930A1 (en) * 2012-07-13 2014-01-16 Semiconductor Energy Laboratory Co., Ltd. Organic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device
TWI612051B (zh) * 2013-03-01 2018-01-21 半導體能源研究所股份有限公司 有機金屬錯合物、發光元件、發光裝置、電子裝置、照明設備
US9231217B2 (en) * 2013-11-28 2016-01-05 Semiconductor Energy Laboratory Co., Ltd. Synthesis method of organometallic complex, synthesis method of pyrazine derivative, 5,6-diaryl-2-pyrazyl triflate, light-emitting element, light-emitting device, electronic device, and lighting device
US9506149B2 (en) * 2014-01-16 2016-11-29 The United States Of America, As Represented By The Secretary Of Commerce Liquid deposition composition and process for forming metal therefrom

Also Published As

Publication number Publication date
US9231217B2 (en) 2016-01-05
US20150147840A1 (en) 2015-05-28
US9586909B2 (en) 2017-03-07
CN104672152A (zh) 2015-06-03
JP2015127321A (ja) 2015-07-09
US20160108006A1 (en) 2016-04-21
CN104672152B (zh) 2018-09-21

Similar Documents

Publication Publication Date Title
JP5738459B2 (ja) 有機化合物
KR102509231B1 (ko) 헤테로고리 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
JP6968926B2 (ja) 有機化合物及び複核錯体
JPWO2019220276A1 (ja) 有機化合物、発光素子、発光装置、電子機器、照明装置および電子デバイス
JP6598513B2 (ja) 有機金属イリジウム錯体、発光素子、発光装置、電子機器、および照明装置
CN103347886A (zh) 有机金属配合物、发光元件、发光装置、电子设备以及照明装置
JP6697299B2 (ja) 有機金属錯体、発光素子、発光装置、電子機器、および照明装置
JP2021004241A (ja) 有機化合物、発光素子、発光装置、電子機器および照明装置
JP2016121125A (ja) 有機金属イリジウム錯体、発光素子、発光装置、電子機器、照明装置、および有機金属イリジウム錯体の合成方法
JP2016069376A (ja) 有機金属イリジウム錯体、発光素子、発光装置、電子機器、および照明装置
JP2022037010A (ja) 発光素子、発光装置、電子機器及び照明装置
US9586909B2 (en) Compound of synthetic intermediate
JP2019011354A (ja) ジベンゾ［ｆ，ｈ］キノキサリン誘導体の合成方法、ジベンゾ［ｆ，ｈ］キノキサリン誘導体、発光装置、電子機器および照明装置
JP6584073B2 (ja) 有機金属錯体および発光装置

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20171120

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20171120

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20180802

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20180807

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20181003

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20181225

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190213

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: 20190611

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20190711

R150 Certificate of patent or registration of utility model

Ref document number: 6557002

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

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