CN1861618A - 有机金属化合物及其有机电致发光显示装置和制造方法 - Google Patents
有机金属化合物及其有机电致发光显示装置和制造方法 Download PDFInfo
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- CN1861618A CN1861618A CNA2006100758096A CN200610075809A CN1861618A CN 1861618 A CN1861618 A CN 1861618A CN A2006100758096 A CNA2006100758096 A CN A2006100758096A CN 200610075809 A CN200610075809 A CN 200610075809A CN 1861618 A CN1861618 A CN 1861618A
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Images
Classifications
-
- 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 radiating surfaces
- H05B33/14—Light 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B62—LAND VEHICLES FOR TRAVELLING OTHERWISE THAN ON RAILS
- B62M—RIDER PROPULSION OF WHEELED VEHICLES OR SLEDGES; POWERED PROPULSION OF SLEDGES OR SINGLE-TRACK CYCLES; TRANSMISSIONS SPECIALLY ADAPTED FOR SUCH VEHICLES
- B62M3/00—Construction of cranks operated by hand or foot
- B62M3/08—Pedals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B62—LAND VEHICLES FOR TRAVELLING OTHERWISE THAN ON RAILS
- B62M—RIDER PROPULSION OF WHEELED VEHICLES OR SLEDGES; POWERED PROPULSION OF SLEDGES OR SINGLE-TRACK CYCLES; TRANSMISSIONS SPECIALLY ADAPTED FOR SUCH VEHICLES
- B62M3/00—Construction of cranks operated by hand or foot
- B62M3/16—Accessories
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
Claims (12)
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KR1020050033083A KR100611885B1 (ko) | 2005-04-21 | 2005-04-21 | 호스트용 화합물과 도판트용 화합물이 연결된 유기 금속화합물, 이를 이용한 유기 전계 발광 소자 및 그의제조방법 |
KR1020050033083 | 2005-04-21 | ||
KR10-2005-0033083 | 2005-04-21 |
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CN1861618A true CN1861618A (zh) | 2006-11-15 |
CN1861618B CN1861618B (zh) | 2010-06-23 |
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CN2006100758096A Active CN1861618B (zh) | 2005-04-21 | 2006-04-18 | 有机金属化合物及其有机电致发光显示装置和制造方法 |
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US (1) | US7541100B2 (zh) |
EP (1) | EP1743900B1 (zh) |
JP (1) | JP4481936B2 (zh) |
KR (1) | KR100611885B1 (zh) |
CN (1) | CN1861618B (zh) |
DE (1) | DE602006002196D1 (zh) |
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KR100732823B1 (ko) * | 2005-04-21 | 2007-06-27 | 삼성에스디아이 주식회사 | 호스트용 화합물과 도판트용 화합물이 연결된 유기 금속화합물, 이를 이용한 유기 전계 발광 소자 및 그의제조방법 |
JP5294242B2 (ja) * | 2007-05-10 | 2013-09-18 | 独立行政法人産業技術総合研究所 | 金属配位化合物ならびにこれを用いた発光材料 |
JP5624270B2 (ja) * | 2007-09-18 | 2014-11-12 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
US8815411B2 (en) * | 2007-11-09 | 2014-08-26 | The Regents Of The University Of Michigan | Stable blue phosphorescent organic light emitting devices |
US8476822B2 (en) * | 2007-11-09 | 2013-07-02 | Universal Display Corporation | Saturated color organic light emitting devices |
WO2009064661A1 (en) * | 2007-11-15 | 2009-05-22 | Nitto Denko Corporation | Light emitting devices and compositions |
US8420231B2 (en) * | 2008-10-08 | 2013-04-16 | Samsung Electronics Co., Ltd. | Iridium phosphorescent dendrimer, method of preparing the same and electroluminescent device including the iridium phosphorescent dendrimer |
JP2012505298A (ja) | 2008-10-13 | 2012-03-01 | 日東電工株式会社 | 印刷可能な発光組成物 |
WO2011024761A1 (ja) | 2009-08-27 | 2011-03-03 | 住友化学株式会社 | 金属錯体組成物及び錯体高分子 |
WO2011024737A1 (ja) | 2009-08-27 | 2011-03-03 | 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 |
US9236578B2 (en) * | 2010-07-30 | 2016-01-12 | Merck Patent Gmbh | Organic electroluminescent device |
CN103907217B (zh) | 2011-09-12 | 2016-10-12 | 新日铁住金化学株式会社 | 有机电致发光元件 |
KR20140076572A (ko) | 2011-09-12 | 2014-06-20 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | 함규소 4원환구조를 가지는 유기전계발광 소자용 재료 및 유기전계발광 소자 |
CN103797602B (zh) | 2011-09-12 | 2016-03-23 | 新日铁住金化学株式会社 | 有机电致发光元件 |
JP6006732B2 (ja) | 2011-12-12 | 2016-10-12 | 新日鉄住金化学株式会社 | 有機電界発光素子用材料及びそれを用いた有機電界発光素子 |
US9985219B2 (en) | 2012-03-12 | 2018-05-29 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element |
WO2014002629A1 (ja) | 2012-06-28 | 2014-01-03 | 新日鉄住金化学株式会社 | 有機電界発光素子用材料及び有機電界発光素子 |
CN104471734B (zh) | 2012-07-19 | 2016-11-09 | 新日铁住金化学株式会社 | 有机电场发光元件 |
TWI599570B (zh) | 2012-09-28 | 2017-09-21 | 新日鐵住金化學股份有限公司 | Compounds for organic electroluminescent devices and organic electroluminescent devices |
US10141523B2 (en) * | 2014-02-25 | 2018-11-27 | Lg Chem, Ltd. | Solution processable red-emitting iridium (III) complex and organic electroluminescence device including the same |
KR101929238B1 (ko) * | 2016-01-14 | 2018-12-14 | 고려대학교 세종산학협력단 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
US11239432B2 (en) * | 2016-10-14 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
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Publication number | Priority date | Publication date | Assignee | Title |
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US6303238B1 (en) * | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
US6830828B2 (en) * | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
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 |
EP1407501B1 (en) | 2001-06-20 | 2009-05-20 | Showa Denko K.K. | Light emitting material and organic light-emitting device |
US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
JP2003073387A (ja) | 2001-09-04 | 2003-03-12 | Canon Inc | 金属配位化合物及び有機発光素子 |
AU2003214421A1 (en) * | 2002-03-18 | 2003-09-29 | Isis Innovation Limited | Phosphorescent dendrimers for use in light-emitting devices |
CN100340630C (zh) | 2002-08-16 | 2007-10-03 | 南加利福尼亚大学 | 有机发光材料和器件 |
US7338722B2 (en) * | 2003-03-24 | 2008-03-04 | The University Of Southern California | Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir |
US6830834B2 (en) * | 2003-04-29 | 2004-12-14 | Canon Kabushiki Kaisha | Organic light emitting devices with host-guest bonding |
JP4198654B2 (ja) | 2003-08-07 | 2008-12-17 | 三星エスディアイ株式会社 | イリジウム化合物及びそれを採用した有機電界発光素子 |
KR100522702B1 (ko) * | 2003-12-03 | 2005-10-19 | 삼성에스디아이 주식회사 | 이리듐 화합물 및 이를 이용한 유기 전계 발광 소자 |
KR100522784B1 (ko) * | 2003-12-13 | 2005-10-19 | (주)그라쎌 | 고효율 적색 발광 재료 및 이를 도판트로서 채용하고 있는표시 소자 |
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- 2006-04-05 DE DE602006002196T patent/DE602006002196D1/de active Active
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EP1743900A1 (en) | 2007-01-17 |
KR100611885B1 (ko) | 2006-08-11 |
CN1861618B (zh) | 2010-06-23 |
EP1743900B1 (en) | 2008-08-13 |
JP4481936B2 (ja) | 2010-06-16 |
US20060237715A1 (en) | 2006-10-26 |
US7541100B2 (en) | 2009-06-02 |
EP1743900A8 (en) | 2007-05-09 |
JP2006298900A (ja) | 2006-11-02 |
DE602006002196D1 (de) | 2008-09-25 |
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