JP4981252B2 - 電界発光材料 - Google Patents
電界発光材料 Download PDFInfo
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- JP4981252B2 JP4981252B2 JP2004501422A JP2004501422A JP4981252B2 JP 4981252 B2 JP4981252 B2 JP 4981252B2 JP 2004501422 A JP2004501422 A JP 2004501422A JP 2004501422 A JP2004501422 A JP 2004501422A JP 4981252 B2 JP4981252 B2 JP 4981252B2
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- 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
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- 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
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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
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- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
例えば、quadridentateなアゾメチン−亜鉛複合体は、有機発光装置の青色光エミッタとして用いられてきたが、その輝度は、最高でも約1000cd/m2に過ぎなかった(Jpn.J.Appl.Phys.,32,L511(1993年);米国特許:第5,432,014号)。
以上のことから、OLEDにおけるホストとドーパントとの間で効率の良いエネルギー転移を可能とし、その一方で、かなり高いドーピング濃度においても自己消滅をほとんど又は全く生じさせない、という発光ドーパント素材を開発すことが求められている。
先ず、本発明の主たる目的は、新しい発光素材でドーピングした有機発光装置(OLED)を提供することである。当該装置は、ターンオン電圧が低く、輝度および効率が高いものとなる。
また、本発明は、熱的に安定した耐湿性の金属キレート素材であって、公知の厚みの薄い層の形で、蒸着プロセスによって塗布することが可能である、という素材を提供することを目的とする。
ここでの例が示すのは、配位子1a、2aおよびプラチナ複合体1b、2bの合成方法である。QuadridentateなONNO型配位子1a、2aについては、文献(J.Chem.Soc.,Perkin Trans.2,863,(1998年))にある手順を変更して実施することで用意したものである。ONNO型配位子を用意する方法については、別の例が「米国特許:第6,177,419号」で報告されている。
(例1)
・1aの合成
(例2)
・1bの合成
(例3)
・2aの合成
(例4)
・2bの合成
本発明によるプラチナ複合体1b、2bのスペクトル特性を表1に示す。複合体1bの場合、250〜350nm(ε=38400−17500dm3mol-1cm-1)に強力な吸収帯が、λmax398nm(ε=10800dm3mol-1cm-1)にやや強い吸収帯が見られる(図1参照)。加えて、ca.480nm(2800dm3mol-1cm-1)にも広い吸収帯が見られる。複合体2bの場合(図1参照)、CH2Cl2の中で、291〜375nm(ε=39200−24700dm3mol-1cm-1)にいくつかの振動遷移が見られ、504nm(ε=7200dm3mol-1cm-1)に広い帯域が見られる。
(例5)
装置Aは以下のように組み立てる。先ず、ガラス基板の上に、20Ω/squareの面積抵抗を備えるインジウムスズ酸化物(ITO)の電極を設ける。そこに、500Åの厚みを有する正孔輸送素材NPB(α-naphthylphenylbiphenyl amine)を設ける。さらに、0.3wt%の複合体1bと青色発光材料Bepp2(beryllium bis(2-(2´-hydroxyphenyl) pyridine)との混合物で成る発光層を400Åの厚みで設ける。そして、15Åの厚みを有する強化電荷移動層LiF、2000Åの厚みを有するアルミニウム層を設ける。金属層および有機層は順番に、5×10-6ミリバールの環境で積層させられ、別々に行われる複数の真空蒸着プロセスにおいては、プロセスとプロセスとの間で真空状態が保たれるようにした。各層は、1秒当たり2Åまたは5Åの速度で蒸着させた。装置の発光領域はカソードとアノードとが重なった領域によって形作られており、3×3mm2の大きさとなった。ITOでコートしたガラス製スライドは、有機溶剤(アセトン・イソプロパノール・メタノール)、脱イオン水、それに続いて紫外線オゾンクリーナを用いて洗浄した。装置のELスペクトルおよび「電流密度−電圧−輝度」の特性については、分光光度計とコンピュータ制御直流電源とを用い、それぞれ室温で計測した。
(例6)
図6(a)および図6(b)は、複合体1bのドーピングレベルが0.3wt%の場合の装置Aの性能を示す。装置が順バイアスの元で駆動される場合には、453nmと540nmの2箇所で強いEL発光が見られる。また、装置Aに関する電流密度−電圧−輝度特性の曲線も示してある。ターンオン電圧は約6〜7Vである。装置の最大効率は、2849cd/m2の輝度において4.1cd/Aであった。最大輝度である9325cd/m2は、10Vの駆動電圧において得られた。装置AのEL色は黄色(CIE座標:x=0.33,y=0.47)である。
(例7)
図7(a)および図7(b)は、複合体1bのドーピングレベルが1.0wt%の場合の装置Bの性能を示す。本装置が示す強いEL発光のピークは546nmにあり、457nmには弱発光が見られる。装置Bのオンセット電圧は約6〜7Vであった。効率および最大輝度はそれぞれ、輝度1927cd/m2において1.9cd/A、9.5Vの駆動電圧において6563cd/m2であった。装置BのEL色は黄色(CIE座標:x=0.39,y=0.54)である。
(例8)
複合体1bのドーピングレベルが2.0wt%である装置Cでは、強いEL発光のピークは548nmに見られ、非常に弱い発光が450nm周辺に見られる(図8)。EL効率は1.5cd/Aと検知された。12Vの駆動電圧では、6450cd/m2の輝度が観測された。装置CのEL色は黄色(CIE座標:x=0.42,y=0.56)である。
Claims (12)
- アノードと正孔輸送層とマトリックス発光層と電荷輸送層とカソードとを少なくとも有し、電界発光を発生させる有機発光装置における発光層であって、少なくともホスト素材と発光分子とを有し、前記発光分子は前記ホスト素材の中でドーパントとして存在する、という発光層であり、
前記発光分子の化学構造は、下に示す式Iまたは式IIで表すことができ、
を特徴とする発光層。 - 前記発光分子は、前記ホスト素材の中に低濃度のドーパントとして提供され、ホスト素材の重量を基準として0.3から2.0重量%を有すること、
を特徴とする請求項1に記載の発光層。 - 黄色の電界発光を生じること、
を特徴とする請求項1に記載の発光層。 - 前記ホスト素材は、beryllium bis(2-(2´-hydroxyphenyl) pyridine) (Bepp2)であること、
を特徴とする請求項1に記載の発光層。 - 前記ホスト素材および前記発光分子は、昇華蒸着または真空蒸着、または蒸気蒸着、またはスピンコートによって、薄膜の形で蒸着することが可能であること、
を特徴とする請求項1に記載の発光層。 - 請求項2に記載の発光層を有する有機発光装置によって発せられる光(CIE座標)を、ドーパントとして提供される前記発光分子の重量%を変化させることによって調節する方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/137,272 | 2002-05-01 | ||
US10/137,272 US6653654B1 (en) | 2002-05-01 | 2002-05-01 | Electroluminescent materials |
PCT/CN2003/000221 WO2003093283A1 (en) | 2002-05-01 | 2003-03-27 | Electroluminescent materials |
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JP2009185012A Division JP2010050451A (ja) | 2002-05-01 | 2009-08-07 | 電界発光材料 |
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JP2005524727A JP2005524727A (ja) | 2005-08-18 |
JP4981252B2 true JP4981252B2 (ja) | 2012-07-18 |
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JP2004501422A Expired - Lifetime JP4981252B2 (ja) | 2002-05-01 | 2003-03-27 | 電界発光材料 |
JP2009185012A Pending JP2010050451A (ja) | 2002-05-01 | 2009-08-07 | 電界発光材料 |
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JP2009185012A Pending JP2010050451A (ja) | 2002-05-01 | 2009-08-07 | 電界発光材料 |
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US (1) | US6653654B1 (ja) |
EP (1) | EP1499624B1 (ja) |
JP (2) | JP4981252B2 (ja) |
KR (1) | KR100991874B1 (ja) |
CN (1) | CN100509827C (ja) |
AU (1) | AU2003218866A1 (ja) |
TW (1) | TWI267544B (ja) |
WO (1) | WO2003093283A1 (ja) |
Families Citing this family (139)
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JP2004275542A (ja) * | 2003-03-17 | 2004-10-07 | Olympus Corp | カプセル型内視鏡 |
JP2004335122A (ja) * | 2003-04-30 | 2004-11-25 | Takasago Internatl Corp | 発光素子 |
JP2004331508A (ja) * | 2003-04-30 | 2004-11-25 | Takasago Internatl Corp | 白金錯体 |
WO2004099339A1 (en) * | 2003-05-09 | 2004-11-18 | Fuji Photo Film Co., Ltd. | Organic electroluminescent device and platinum compound |
EP3623444B1 (en) | 2003-06-02 | 2021-05-26 | UDC Ireland Limited | Organic electroluminescent devices and metal complex compounds |
US7029766B2 (en) | 2003-12-05 | 2006-04-18 | Eastman Kodak Company | Organic element for electroluminescent devices |
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KR100600862B1 (ko) * | 2004-01-30 | 2006-07-14 | 김선권 | 인터넷상의 정보자원에 대한 접근 경로를 체계적으로수집하고 검색하는 방법, 및 이 방법을 실행할 수 있는컴퓨터 프로그램을 수록한 기록매체 |
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JP4749744B2 (ja) * | 2004-03-31 | 2011-08-17 | 富士フイルム株式会社 | 有機電界発光素子 |
US7361415B2 (en) * | 2004-04-16 | 2008-04-22 | The University Of Hong Kong | System and method for producing light with organic light-emitting devices |
US20050244672A1 (en) * | 2004-04-30 | 2005-11-03 | Chi-Ming Che | Organic light-emitting devices |
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JP5008974B2 (ja) * | 2004-05-18 | 2012-08-22 | 日本放送協会 | 発光素子 |
US7238301B2 (en) * | 2004-06-29 | 2007-07-03 | Kimberly-Clark Worldwide, Inc. | Cross-linked encapsulated phosphorescent molecules |
DE102004034517A1 (de) * | 2004-07-16 | 2006-02-16 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
JP4813032B2 (ja) * | 2004-09-21 | 2011-11-09 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4500735B2 (ja) * | 2004-09-22 | 2010-07-14 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4531509B2 (ja) * | 2004-09-27 | 2010-08-25 | 富士フイルム株式会社 | 発光素子 |
JP4762527B2 (ja) | 2004-11-10 | 2011-08-31 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4903416B2 (ja) * | 2004-11-10 | 2012-03-28 | 富士フイルム株式会社 | 有機電界発光素子 |
JP2006140218A (ja) * | 2004-11-10 | 2006-06-01 | Fuji Photo Film Co Ltd | 有機電界発光素子 |
US20060105202A1 (en) * | 2004-11-17 | 2006-05-18 | Fuji Photo Film Co., Ltd. | Organic electroluminescent device |
JP4969086B2 (ja) * | 2004-11-17 | 2012-07-04 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4773109B2 (ja) * | 2005-02-28 | 2011-09-14 | 高砂香料工業株式会社 | 白金錯体及び発光素子 |
US7771845B2 (en) * | 2005-03-14 | 2010-08-10 | Fujifilm Corporation | Organic electroluminescent device |
JP4727262B2 (ja) * | 2005-03-16 | 2011-07-20 | 富士フイルム株式会社 | 有機電界発光素子 |
TWI391027B (zh) * | 2005-04-25 | 2013-03-21 | Fujifilm Corp | 有機電致發光裝置 |
JP4934346B2 (ja) * | 2005-04-25 | 2012-05-16 | 富士フイルム株式会社 | 有機電界発光素子 |
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JP2891783B2 (ja) * | 1991-02-06 | 1999-05-17 | パイオニア株式会社 | 有機エレクトロルミネッセンス素子 |
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US6310360B1 (en) | 1999-07-21 | 2001-10-30 | The Trustees Of Princeton University | Intersystem crossing agents for efficient utilization of excitons in organic light emitting devices |
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JP2010050451A (ja) | 2010-03-04 |
AU2003218866A1 (en) | 2003-11-17 |
EP1499624A1 (en) | 2005-01-26 |
KR100991874B1 (ko) | 2010-11-04 |
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EP1499624B1 (en) | 2016-01-06 |
JP2005524727A (ja) | 2005-08-18 |
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EXPY | Cancellation because of completion of term |