KR100832766B1 - 붕소 또는 알루미늄계 스피로 화합물 및 전자 산업에서의이들의 용도 - Google Patents
붕소 또는 알루미늄계 스피로 화합물 및 전자 산업에서의이들의 용도 Download PDFInfo
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- KR100832766B1 KR100832766B1 KR1020037008396A KR20037008396A KR100832766B1 KR 100832766 B1 KR100832766 B1 KR 100832766B1 KR 1020037008396 A KR1020037008396 A KR 1020037008396A KR 20037008396 A KR20037008396 A KR 20037008396A KR 100832766 B1 KR100832766 B1 KR 100832766B1
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Images
Classifications
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- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
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- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/062—Al linked exclusively to C
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Photoreceptors In Electrophotography (AREA)
Abstract
Description
Claims (13)
- 하기 화학식 I의 화합물:[화학식 I]{위의 화학식 I에서,Q', Q", Q'" 및 Q""는 각각 동일하거나 상이하고, 각각 CN, F 또는 탄소수 1 내지 20의 직쇄 또는 측쇄 또는 사이클릭 알킬기(여기서, 인접하지 않은 하나 이상의 CH2기는 -O-, -CO- 또는 -COO- 에 의해 치환될 수 있고, 하나 이상의 H 원자는 F에 의해 치환될 수 있다), 또는 탄소수 4 내지 14의 아릴 또는 헤테로아릴기(이는 하나 이상의 비방향족 라디칼 Q'에 의해 치환될 수 있다)이고,n은 동일하거나 상이하고, 각각 0 또는 1이며,X는 -CH- 또는 N이고,Y1 내지 Y6는 2개 이상의 동일하거나 상이한 하기 화학식 II의 치환기를 포함하고, 화학식 II가 점유하지 않은 방향족 위치에서의 나머지 Y1 내지 Y6은 동일하거나 상이한 치환기 Q' 또는 H이다:[화학식 II](위의 화학식 II에서,Aryl1 및 Aryl2는 각각 동일하거나 상이하고, 각각 페닐, 1- 또는 2-나프틸, 1-, 2- 또는 9-안트라세닐, 2-, 3- 또는 4-피리디닐, 2-, 4- 또는 5-피리미디닐, 2-피라지닐, 3- 또는 4-피리다지닐, 2-, 3-, 4-, 5-, 6-, 7- 또는 8-퀴놀리닐, 2- 또는 3-티에닐, 2- 또는 3-피롤릴, 2- 또는 3-푸라닐 또는 2-(1,3,4-옥사디아졸릴)일이고,R' 및 R"는 각각 동일하거나 상이하고, 각각 CN, F 또는 탄소수 1 내지 20의 직쇄 또는 측쇄 또는 사이클릭 알킬기(여기서, 인접하지 않은 하나 이상의 CH2기는 -O-, -CO- 또는 -COO- 에 의해 치환될 수 있고, 하나 이상의 H 원자는 F에 의해 치환될 수 있다), 또는 탄소수 4 내지 14의 아릴 또는 헤테로아릴기(이는 하나 이상의 비방향족 라디칼 R'에 의해 치환될 수 있다)이며,m은 동일하거나 상이하고, 각각 0, 1, 2 또는 3이며,Z는 붕소 또는 알루미늄이다)}.
- 제1항에 있어서, X가 -CH-임을 특징으로 하는 화합물.
- 제1항 또는 제2항에 있어서, 치환기 Y1 내지 Y6 중의 아릴 치환기 Aryl1 및 Aryl2가 각각 페닐, 1-나프틸, 2-나프틸 또는 9-안트라세닐임을 특징으로 하는 화합물.
- 제1항 또는 제2항에 있어서, Z가 붕소임을 특징으로 하는 화합물.
- 제1항 또는 제2항에 있어서, 치환기 Y5 및 Y6이 Q' 및 수소임을 특징으로 하는 화합물.
- 하기 화학식 IV의 화합물:[화학식 IV]{위의 화학식 IV에서,Y1 내지 Y4는 2개 이상의 동일하거나 상이한 하기 화학식 V의 치환기를 포함하고, 화학식 V가 점유하지 않은 방향족 위치에서의 나머지 Y1 내지 Y4는 동일하거나 상이한 치환기 Q' 또는 H이다:[화학식 V](위의 화학식 V에서,n은 동일하거나 상이하고, 각각 0, 1 또는 2이고,R1, R2, R3 및 R4는 동일하거나 상이하고, 각각 탄소수 1 내지 20의 알킬, 알킬옥시 또는 알릴 라디칼이며,R5 및 R6은 동일하거나 상이하고, 각각 H, CN, F, Cl, Br, I, 직쇄, 측쇄 또는 사이클릭 알킬 또는 알콕시기, 티오알킬 또는 티오아릴기, 니트로기, 디아릴아미노 또는 디알킬아미노기 또는 에스테르, 아미드 또는 카복실기(여기서, 알킬, 알콕시 또는 아릴기는 탄소수가 1 내지 20이다)이다)}.
- 제6항에 있어서, 라디칼 Y1 내지 Y4 중의 2개, 3개 또는 4개가 동일한 것을 특징으로 하는 화합물.
- 유기 전기발광 및/또는 인광 디바이스에서 제1항, 제2항, 제6항 또는 제7항 중 어느 한 항에 따른 화합물을 사용하는 방법.
- 유기 전기발광 및/또는 인광 디바이스에서 전자 운송층(ETL), 홀 차단층(HBL) 및/또는 호스트 재료로서 제1항, 제2항, 제6항 또는 제7항 중 어느 한 항에 따른 화합물을 사용하는 방법.
- 사진 복사기에서 전자 운송 재료로서 제1항, 제2항, 제6항 또는 제7항 중 어느 한 항에 따른 화합물을 사용하는 방법.
- 태양 전지에서 전자 수용체 또는 전자 운송 재료로서 제1항, 제2항, 제6항 또는 제7항 중 어느 한 항에 따른 화합물을 사용하는 방법.
- 유기 IC(회로)에서 전하 운송 재료로서 제1항, 제2항, 제6항 또는 제7항 중 어느 한 항에 따른 화합물을 사용하는 방법.
- 유기 고상 레이저 또는 유기 광검출기에서 제1항, 제2항, 제6항 또는 제7항 중 어느 한 항에 따른 화합물을 사용하는 방법.
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EP00128292 | 2000-12-22 | ||
EP00128292.0 | 2000-12-22 | ||
PCT/EP2001/015177 WO2002051850A1 (de) | 2000-12-22 | 2001-12-20 | Bor- oder aluminium-spiroverbindungen, deren verwendung in electronikindustrie |
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KR20040023579A KR20040023579A (ko) | 2004-03-18 |
KR100832766B1 true KR100832766B1 (ko) | 2008-05-27 |
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KR1020037008396A KR100832766B1 (ko) | 2000-12-22 | 2001-12-20 | 붕소 또는 알루미늄계 스피로 화합물 및 전자 산업에서의이들의 용도 |
Country Status (7)
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US (1) | US6911551B2 (ko) |
EP (1) | EP1345948B1 (ko) |
JP (1) | JP4068461B2 (ko) |
KR (1) | KR100832766B1 (ko) |
CN (1) | CN1221555C (ko) |
DE (1) | DE50104149D1 (ko) |
WO (1) | WO2002051850A1 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011002109A1 (en) * | 2009-06-30 | 2011-01-06 | Soonchunhyang University Industry Academy Cooperation Foundation | Organic light emitting device |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1217668A1 (de) * | 2000-12-22 | 2002-06-26 | Covion Organic Semiconductors GmbH | Verwendung von Bor- und Aluminium-Verbindungen in Elektronik-Bauteilen |
JP4804662B2 (ja) * | 2001-07-11 | 2011-11-02 | 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及び表示装置 |
JP4300788B2 (ja) * | 2001-12-06 | 2009-07-22 | 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および表示装置 |
US20060063027A1 (en) * | 2002-12-23 | 2006-03-23 | Covion Organic Semiconductors Gmbh | Organic electroluminescent element |
WO2005011334A1 (de) * | 2003-07-21 | 2005-02-03 | Covion Organic Semiconductors Gmbh | Organisches elektrolumineszenzelement |
DE102004034140A1 (de) * | 2004-07-15 | 2006-02-23 | Covion Organic Semiconductors Gmbh | Verwendung von Polymeren für Up-conversion und Vorrichtungen zur Up-conversion |
EP1888706B1 (de) * | 2005-05-03 | 2017-03-01 | Merck Patent GmbH | Organische elektrolumineszenzvorrichtung und in deren herstellung verwendete boronsäure- und borinsäure-derivate |
US20070201239A1 (en) * | 2005-07-13 | 2007-08-30 | Daniel Rosario | Display Device For A Vehicle |
US20070116984A1 (en) * | 2005-09-21 | 2007-05-24 | Doosan Corporation | Spiro-compound for electroluminescent display device and electroluminescent display device comprising the same |
KR100798817B1 (ko) * | 2006-07-28 | 2008-01-28 | 주식회사 두산 | 전계 발광 소자용 스피로 화합물, 및 이를 포함하는 전계발광 소자 |
CN100358904C (zh) * | 2005-10-12 | 2008-01-02 | 友达光电股份有限公司 | 螺环硅烷化合物及其应用的有机电致发光显示器件 |
KR101156529B1 (ko) * | 2005-10-18 | 2012-06-20 | 삼성에스디아이 주식회사 | 신규한 홀 전달물질 및 이를 이용한 고체전해질 및광전변환소자 |
KR100828173B1 (ko) * | 2005-11-22 | 2008-05-08 | (주)그라쎌 | 유기 발광 화합물 및 이를 발광재료로 채용하고 있는 표시소자 |
DE102008048540A1 (de) * | 2008-09-15 | 2010-04-15 | Gebr. Schmid Gmbh & Co. | Verfahren zur Behandlung von Substraten, Substrat und Behandlungseinrichtung zur Durchführung des Verfahrens |
DE102009032922B4 (de) | 2009-07-14 | 2024-04-25 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen, Verfahren zu deren Herstellung, deren Verwendung sowie elektronische Vorrichtung |
CN105612164A (zh) * | 2013-10-02 | 2016-05-25 | 默克专利有限公司 | 用于oled中的含硼化合物 |
JP6772188B2 (ja) | 2015-02-03 | 2020-10-21 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | 金属錯体 |
KR102399570B1 (ko) | 2015-11-26 | 2022-05-19 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US11910707B2 (en) | 2015-12-23 | 2024-02-20 | Samsung Display Co., Ltd. | Organic light-emitting device |
KR20170127101A (ko) | 2016-05-10 | 2017-11-21 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
CN105801609B (zh) * | 2016-06-03 | 2018-08-10 | 苏州大学 | 一种硼类材料及其制备方法和应用 |
TWI776926B (zh) | 2017-07-25 | 2022-09-11 | 德商麥克專利有限公司 | 金屬錯合物 |
CN111406062B (zh) | 2017-12-13 | 2024-01-19 | Udc爱尔兰有限公司 | 金属络合物 |
CN111699192B (zh) | 2018-02-13 | 2024-03-08 | Udc爱尔兰有限公司 | 金属络合物 |
KR20210125531A (ko) | 2019-02-11 | 2021-10-18 | 메르크 파텐트 게엠베하 | 3개의 오르토-메탈레이트화 두자리 리간드 및 광학 배향 이방성을 포함하는 단핵 이리듐 착물 |
EP4069709A1 (de) | 2019-12-04 | 2022-10-12 | Merck Patent GmbH | Metallkomplexe |
EP4222155A1 (de) | 2020-09-29 | 2023-08-09 | Merck Patent GmbH | Mononukleare tripodale hexadentate iridium komplexe zur verwendung in oleds |
EP4079742A1 (de) | 2021-04-14 | 2022-10-26 | Merck Patent GmbH | Metallkomplexe |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4436773A1 (de) * | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
-
2001
- 2001-12-20 US US10/250,593 patent/US6911551B2/en not_active Expired - Lifetime
- 2001-12-20 DE DE50104149T patent/DE50104149D1/de not_active Expired - Lifetime
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4436773A1 (de) * | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
Non-Patent Citations (1)
Title |
---|
Advanced Materials, 1999, 11(4), pp. 283-285 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011002109A1 (en) * | 2009-06-30 | 2011-01-06 | Soonchunhyang University Industry Academy Cooperation Foundation | Organic light emitting device |
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WO2002051850A1 (de) | 2002-07-04 |
CN1221555C (zh) | 2005-10-05 |
CN1483036A (zh) | 2004-03-17 |
JP4068461B2 (ja) | 2008-03-26 |
EP1345948B1 (de) | 2004-10-13 |
JP2004525878A (ja) | 2004-08-26 |
US6911551B2 (en) | 2005-06-28 |
KR20040023579A (ko) | 2004-03-18 |
US20040063981A1 (en) | 2004-04-01 |
EP1345948A1 (de) | 2003-09-24 |
DE50104149D1 (de) | 2004-11-18 |
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