JP2006513278A5 - - Google Patents
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- Publication number
- JP2006513278A5 JP2006513278A5 JP2004529129A JP2004529129A JP2006513278A5 JP 2006513278 A5 JP2006513278 A5 JP 2006513278A5 JP 2004529129 A JP2004529129 A JP 2004529129A JP 2004529129 A JP2004529129 A JP 2004529129A JP 2006513278 A5 JP2006513278 A5 JP 2006513278A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- electron
- aryl
- light emitting
- heteroaryl
- 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.)
- Granted
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- 239000000203 mixture Substances 0.000 claims description 29
- 239000012044 organic layer Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 55
- 125000003118 aryl group Chemical group 0.000 claims 54
- -1 trifluorovinyl Chemical group 0.000 claims 47
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 43
- 239000000463 material Substances 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 37
- 229910052736 halogen Inorganic materials 0.000 claims 30
- 150000002367 halogens Chemical class 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 22
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 229910052751 metal Inorganic materials 0.000 claims 14
- 239000002184 metal Substances 0.000 claims 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 229910001385 heavy metal Inorganic materials 0.000 claims 9
- 239000003446 ligand Substances 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 229910052697 platinum Inorganic materials 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 229910052741 iridium Inorganic materials 0.000 claims 7
- 229910052787 antimony Inorganic materials 0.000 claims 6
- 229910052797 bismuth Inorganic materials 0.000 claims 6
- 229910052738 indium Inorganic materials 0.000 claims 6
- 229910052745 lead Inorganic materials 0.000 claims 6
- 229910052763 palladium Inorganic materials 0.000 claims 6
- 229910052702 rhenium Inorganic materials 0.000 claims 6
- 229910052703 rhodium Inorganic materials 0.000 claims 6
- 229910052709 silver Inorganic materials 0.000 claims 6
- 229910052718 tin Inorganic materials 0.000 claims 6
- 238000000295 emission spectrum Methods 0.000 claims 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QQLRSCZSKQTFGY-UHFFFAOYSA-N (2,4-difluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(F)C=C1F QQLRSCZSKQTFGY-UHFFFAOYSA-N 0.000 description 1
- SSABEFIRGJISFH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)pyridine Chemical compound FC1=CC(F)=CC=C1C1=CC=CC=N1 SSABEFIRGJISFH-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40421302P | 2002-08-16 | 2002-08-16 | |
| US60/404,213 | 2002-08-16 | ||
| US10/288,785 US6916554B2 (en) | 2002-11-06 | 2002-11-06 | Organic light emitting materials and devices |
| US10/288,785 | 2002-11-16 | ||
| PCT/US2003/025938 WO2004016711A1 (en) | 2002-08-16 | 2003-08-18 | Organic light emitting materials and devices |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2006513278A JP2006513278A (ja) | 2006-04-20 |
| JP2006513278A6 JP2006513278A6 (ja) | 2006-08-17 |
| JP2006513278A5 true JP2006513278A5 (enExample) | 2006-10-05 |
| JP4343838B2 JP4343838B2 (ja) | 2009-10-14 |
Family
ID=31890991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004529129A Expired - Lifetime JP4343838B2 (ja) | 2002-08-16 | 2003-08-18 | 有機発光材料及びデバイス |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7011897B2 (enExample) |
| EP (1) | EP1534799A4 (enExample) |
| JP (1) | JP4343838B2 (enExample) |
| KR (1) | KR20050052473A (enExample) |
| CN (1) | CN100340630C (enExample) |
| AU (1) | AU2003263929A1 (enExample) |
| WO (1) | WO2004016711A1 (enExample) |
Families Citing this family (122)
| 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 |
| KR100493311B1 (ko) * | 2001-02-21 | 2005-06-07 | 엘지전자 주식회사 | 디지털 미디어의 복제 제어를 위한 워터마크기반 복제관리 시스템 및 방법 |
| US7320833B2 (en) * | 2001-11-07 | 2008-01-22 | E.I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
| JP4115788B2 (ja) * | 2002-09-17 | 2008-07-09 | 日本放送協会 | 有機発光材料、有機発光素子およびこれを用いたディスプレイ |
| US7816016B1 (en) | 2003-02-13 | 2010-10-19 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds and devices made therefrom |
| JP2004281087A (ja) * | 2003-03-12 | 2004-10-07 | Nippon Hoso Kyokai <Nhk> | 有機ｅｌデバイスおよび有機ｅｌディスプレイ |
| JP4655454B2 (ja) * | 2003-05-28 | 2011-03-23 | 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、照明装置および表示装置 |
| JP2005071986A (ja) * | 2003-08-04 | 2005-03-17 | Fuji Photo Film Co Ltd | 有機電界発光素子 |
| JP4363133B2 (ja) * | 2003-09-09 | 2009-11-11 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス用素子材料およびそれを用いた有機エレクトロルミネッセンス素子 |
| KR101032590B1 (ko) * | 2003-09-19 | 2011-05-06 | 후지필름 가부시키가이샤 | 유기 전기 발광 소자 |
| KR100577235B1 (ko) | 2004-03-19 | 2006-05-10 | 엘지전자 주식회사 | 유기전계발광소자 |
| KR100565666B1 (ko) | 2004-03-22 | 2006-03-29 | 엘지전자 주식회사 | 유기전계발광소자 |
| US20050211974A1 (en) * | 2004-03-26 | 2005-09-29 | Thompson Mark E | Organic photosensitive devices |
| KR100556421B1 (ko) * | 2004-04-09 | 2006-03-03 | 엘지전자 주식회사 | 청색 인광용 유기 전계 발광 소자 |
| US7279704B2 (en) * | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
| EP1754267A1 (en) * | 2004-06-09 | 2007-02-21 | E.I.Du pont de nemours and company | Organometallic compounds and devices made with such compounds |
| KR100730115B1 (ko) * | 2004-06-23 | 2007-06-19 | 삼성에스디아이 주식회사 | 이리듐 화합물 및 이를 이용한 유기 전계 발광 소자 |
| EP3428986B1 (en) * | 2004-07-07 | 2021-01-20 | Universal Display Corporation | Stable and efficient electroluminescent materials |
| US7402345B2 (en) * | 2004-09-14 | 2008-07-22 | E.I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds |
| DE102004057072A1 (de) * | 2004-11-25 | 2006-06-01 | Basf Ag | Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs) |
| US7242703B2 (en) * | 2004-12-21 | 2007-07-10 | The Trustees Of Princeton University | Organic injection laser |
| JP2006213686A (ja) * | 2005-02-07 | 2006-08-17 | Idemitsu Kosan Co Ltd | 金属錯体化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
| US20090123720A1 (en) * | 2005-03-01 | 2009-05-14 | Zhikuan Chen | Solution processed organometallic complexes and their use in electroluminescent devices |
| JP2006241046A (ja) * | 2005-03-02 | 2006-09-14 | Chemiprokasei Kaisha Ltd | シアノフェニルピリジンイリジウム錯体、それよりなる発光材料およびそれを含有する有機ｅｌ素子。 |
| JP5125502B2 (ja) * | 2005-03-16 | 2013-01-23 | 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材料、有機エレクトロルミネッセンス素子 |
| KR101223717B1 (ko) * | 2005-04-12 | 2013-01-18 | 삼성디스플레이 주식회사 | 실릴 치환된 시클로메탈화 전이금속 착물 및 이를 이용한 유기 전계 발광 소자 |
| KR100611885B1 (ko) | 2005-04-21 | 2006-08-11 | 삼성에스디아이 주식회사 | 호스트용 화합물과 도판트용 화합물이 연결된 유기 금속화합물, 이를 이용한 유기 전계 발광 소자 및 그의제조방법 |
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| JP5076891B2 (ja) | 2005-07-01 | 2012-11-21 | 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材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| KR100729089B1 (ko) | 2005-08-26 | 2007-06-14 | 삼성에스디아이 주식회사 | 유기 발광표시장치 및 그 제조방법 |
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| DE102006030860A1 (de) | 2006-07-04 | 2008-01-10 | Universität Regensburg | Oligomere von Isonitril-Metallkomplexen als Triplett-Emitter für OLED-Anwendungen |
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| TWI555734B (zh) * | 2008-09-16 | 2016-11-01 | 環球展覽公司 | 磷光物質 |
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| DE102008053121A1 (de) | 2008-10-24 | 2010-04-29 | Merck Patent Gmbh | Doppelkomplex-Salze als Emitter in OLED-Vorrichtungen |
| US20110215715A1 (en) * | 2008-11-19 | 2011-09-08 | E.I. Du Pont De Nemours And Company | Chrysene compounds for blue or green luminescent applications |
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| US8932733B2 (en) * | 2008-12-19 | 2015-01-13 | E I Du Pont De Nemours And Company | Chrysene derivative host materials |
| US8531100B2 (en) | 2008-12-22 | 2013-09-10 | E I Du Pont De Nemours And Company | Deuterated compounds for luminescent applications |
| US20120025177A1 (en) * | 2009-02-06 | 2012-02-02 | Solvay Sa | Phosphorescent light-emitting iridium complex containing pyridyltriazole ligand |
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