JP2010525111A - ポリカルバゾリル(メタ)アクリレート発光組成物 - Google Patents
ポリカルバゾリル(メタ)アクリレート発光組成物 Download PDFInfo
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Abstract
【化1】
【選択図】図1
Description
本発明の文脈中では、アルキルは、線状、枝分れ又は環状の炭化水素構造及びこれらの組合せを含むものであり、低級アルキル及び高級アルキルを包含する。好ましいアルキル基はC20以下のものである。低級アルキルは、炭素原子数1〜6、好ましくは炭素原子数1〜4のアルキル基をいい、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、s−ブチル及びt−ブチルが挙げられる。高級アルキルは、炭素原子数7以上、好ましくは炭素原子数7〜20のアルキル基をいい、n−ヘプチル、s−ヘプチル、t−ヘプチル、オクチル及びドデシルが挙げられる。シクロアルキルはアルキルの部分集合であって、炭素原子数3〜8の環状炭化水素基を包含する。シクロアルキル基の例としては、シクロプロピル、シクロブチル、シクロペンチル及びノルボルニルが挙げられる。アルケニル及びアルキニルは、2以上の水素原子がそれぞれ二重結合又は三重結合で置き換えられたアルキル基をいう。
非冷却R928赤色感受性光電子増倍管を備えたPerkin Elmer LS55分光蛍光計を用いてりん光スペクトルを得た。典型的な手順は、ポリマーの試料を清浄な実験室用乳鉢内に配置し、熱的平衡を確保するため、測定前に試料を液体窒素中に2分間以上浸漬することを含んでいた。次に、試料を光学的に励起した。検出ゲートを初期の20マイクロ秒(μs)励起パルスから遅れた時刻に設定したLS55の遅延収集特性を用いることで発光スペクトルを得た。ポリ(2−(9−カルバゾリル)−エチルメタクリレート)及びポリスチレン(PS)中に分散したFIrpic(1wt%)のりん光スペクトルを図1に示す。
冷却R928光電子増倍管を備えたEdinburgh CD920分光計を用いて三重項励起状態の寿命を測定した。典型的な手順では、真空ジュワー瓶内において試料を4×10-5トルの真空下に配置した。次に、パルスダイオードレーザー(パルス幅55ps、繰返し速度10〜40kHz、1〜50nJ/パルス)を用いて試料を394nmで光学的に励起した。時間分解発光スペクトルを470nmで測定した。
2つのりん光性OLEDを作製したが、一方はITO/PEDOT:PSS/PVK:FIrpic:OXD−7/CsF/Alの構造を有する対照品であり、他方はPVKの代わりにポリ(2−(9−カルバゾリル)−エチルメタクリレート)を用いた例示的なデバイスである。クロロベンゼン中の2.0wt%ポリ(2−(9−カルバゾリル)−エチルメタクリレート)1.0mL、クロロベンゼン中の1.0wt%FIrpic 0.20mL、及びクロロベンゼン中の2.0wt%OXD−7 0.30mLを混合することで、ポリ(2−(9−カルバゾリル)−エチルメタクリレート):FIrpic:OXD−7(100:10:30)の溶液を調製した。同様に、PVK溶液、FIrpic溶液及びOXD−7溶液を混合することでPVK:FIrpic:OXD−7(100:10:30)の溶液を調製した。
Claims (36)
- R1がHである、請求項2記載の組成物。
- R1がCH3である、請求項2記載の組成物。
- ポリマーがさらに、アクリル酸、アクリル酸エステル、アクリル酸アミド、メタクリル酸、メタクリル酸エステル、メタクリル酸アミド又はこれらの組合せから導かれる構造単位を含む、請求項1記載の組成物。
- 1種以上のりん光性有機金属化合物が式L2MZを有し、L及びZは独立に二座配位子であり、MはGa、Al、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Y、Zr、Nb、Mo、Tc、Ru、Rh、Pd、Ag、Cd、Lu、Hf、Ta、W、Re、Os、Ir、Pt、Au、Hg、Ga、Ge、In、Sn、Sb、Tl、Pb、Bi、Eu、Tb、La、Po又はこれらの組合せである、請求項1記載の組成物。
- MがIrである、請求項6記載の組成物。
- Lがシクロメタレート化配位子である、請求項6記載の組成物。
- L及びZが独立に、フェニルピリジン、トリルピリジン、ベンゾチエニルピリジン、フェニルイソキノリン、ジベンゾキノザリン、フルオレニルピリジン、ケトピロール、ピコリネート、アセチルアセトネート、ヘキサフルオロアセチルアセトネート、サリチリデン、8−ヒドロキシキノリネート、サリチルアルデヒド、イミノアセトネート、2−(1−ナフチル)ベンゾオキサゾール、2−フェニルベンゾオキサゾール、2−フェニルベンゾチアゾール、クマリン、チエニルピリジン、フェニルピリジン、ベンゾチエニルピリジン、3−メトキシ−2−フェニルピリジン、チエニルピリジン、フェニルイミン、ビニルピリジン、ピリジルナフタレン、ピリジルピロール、ピリジルイミダゾール、フェニルインドール、これらの誘導体又はこれらの組合せから導かれる、請求項6記載の組成物。
- Lが2−(4,6−ジフルオロフェニル)ピリジンから導かれる、請求項9記載の組成物。
- Zがピコリネートから導かれる、請求項6記載の組成物。
- 1種以上のりん光性有機金属化合物が青色りん光色素である、請求項1記載の組成物。
- 1種以上のりん光性有機金属化合物が緑色りん光色素である、請求項1記載の組成物。
- 1種以上のりん光性有機金属化合物が赤色りん光色素である、請求項1記載の組成物。
- R1がHである、請求項20記載のデバイス。
- R1がCH3である、請求項20記載のデバイス。
- ポリマーがさらに、アクリル酸、アクリル酸エステル、アクリル酸アミド、メタクリル酸、メタクリル酸エステル、メタクリル酸アミド、ビニル芳香族モノマー、置換エチレンモノマー又はこれらの組合せから導かれる構造単位を含む、請求項19記載のデバイス。
- 1種以上のりん光性有機金属化合物が式L2MZの化合物であり、L及びZは独立に二座配位子であり、MはGa、Al、Sc、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Y、Zr、Nb、Mo、Tc、Ru、Rh、Pd、Ag、Cd、Lu、Hf、Ta、W、Re、Os、Ir、Pt、Au、Hg、Ga、Ge、In、Sn、Sb、Tl、Pb、Bi、Eu、Tb、La、Po又はこれらの組合せである、請求項19記載のデバイス。
- MがIrである、請求項24記載のデバイス。
- Lがシクロメタレート化配位子である、請求項24記載のデバイス。
- L及びZが独立に、フェニルピリジン、トリルピリジン、ベンゾチエニルピリジン、フェニルイソキノリン、ジベンゾキノザリン、フルオレニルピリジン、ケトピロール、ピコリネート、アセチルアセトネート、ヘキサフルオロアセチルアセトネート、サリチリデン、8−ヒドロキシキノリネート、サリチルアルデヒド、イミノアセトネート、2−(1−ナフチル)ベンゾオキサゾール、2−フェニルベンゾオキサゾール、2−フェニルベンゾチアゾール、クマリン、チエニルピリジン、フェニルピリジン、ベンゾチエニルピリジン、3−メトキシ−2−フェニルピリジン、チエニルピリジン、フェニルイミン、ビニルピリジン、ピリジルナフタレン、ピリジルピロール、ピリジルイミダゾール、フェニルインドール、これらの誘導体又はこれらの組合せから導かれる、請求項24記載のデバイス。
- Lが2−(4,6−ジフルオロフェニル)ピリジンから導かれる、請求項27記載のデバイス。
- Zがピコリネートから導かれる、請求項27記載のデバイス。
- 1種以上のりん光性有機金属化合物が青色りん光色素である、請求項19記載のデバイス。
- 1種以上のりん光性有機金属化合物が緑色りん光色素である、請求項19記載のデバイス。
- 1種以上のりん光性有機金属化合物が赤色りん光色素である、請求項19記載のデバイス。
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US11/736,023 US20080258111A1 (en) | 2007-04-17 | 2007-04-17 | Polycarbazolyl(meth)acrylate light emissive compositions |
PCT/US2008/059106 WO2008130805A1 (en) | 2007-04-17 | 2008-04-02 | Polycarbazolyl(meth)acrylate light emissive compositions |
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EP (1) | EP2139929B1 (ja) |
JP (1) | JP2010525111A (ja) |
KR (1) | KR20100015590A (ja) |
CN (1) | CN101663337B (ja) |
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Cited By (2)
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JP2010525112A (ja) * | 2007-04-17 | 2010-07-22 | ゼネラル・エレクトリック・カンパニイ | ポリカルバゾリル(メタ)アクリレート発光組成物 |
JP2017501263A (ja) * | 2013-12-06 | 2017-01-12 | メルク パテント ゲーエムベーハー | アクリル酸エステルおよび/またはメタクリル酸エステル単位を含むポリマーバインダーを含む組成物 |
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JP5732463B2 (ja) * | 2009-10-05 | 2015-06-10 | トルン ライティング リミテッドThorn Lighting Limited | 多層有機素子 |
US9562136B2 (en) * | 2011-07-04 | 2017-02-07 | Cambridge Display Technology, Ltd. | Polymers, monomers and methods of forming polymers |
US8803187B2 (en) | 2012-10-22 | 2014-08-12 | Empire Technology Development Llc | Protection of light emitting devices |
WO2014065779A2 (en) * | 2012-10-22 | 2014-05-01 | Empire Technology Development Llc | Protection of light emitting devices |
CN105489763B (zh) * | 2015-11-26 | 2018-05-15 | 电子科技大学 | 一种基于铱类配合物磷光材料掺杂的有机紫外探测器件 |
CN106366260B (zh) * | 2016-09-26 | 2018-07-17 | 福建师范大学 | 一种黄光共聚物杂化材料及其制备方法 |
CN106432636B (zh) * | 2016-09-26 | 2018-07-17 | 福建师范大学 | 含poss纳米杂化聚合物磷光材料及其制备方法 |
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JP2010525112A (ja) * | 2007-04-17 | 2010-07-22 | ゼネラル・エレクトリック・カンパニイ | ポリカルバゾリル(メタ)アクリレート発光組成物 |
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Also Published As
Publication number | Publication date |
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CN101663337B (zh) | 2014-05-07 |
US20080258111A1 (en) | 2008-10-23 |
CN101663337A (zh) | 2010-03-03 |
EP2139929A1 (en) | 2010-01-06 |
EP2139929B1 (en) | 2014-10-08 |
WO2008130805A1 (en) | 2008-10-30 |
KR20100015590A (ko) | 2010-02-12 |
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