JP2013065878A - アントラセン誘導体を含むエレクトロルミネッセンス・デバイス - Google Patents
アントラセン誘導体を含むエレクトロルミネッセンス・デバイス Download PDFInfo
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- JP2013065878A JP2013065878A JP2012256308A JP2012256308A JP2013065878A JP 2013065878 A JP2013065878 A JP 2013065878A JP 2012256308 A JP2012256308 A JP 2012256308A JP 2012256308 A JP2012256308 A JP 2012256308A JP 2013065878 A JP2013065878 A JP 2013065878A
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- 125000001424 substituent group Chemical group 0.000 claims description 42
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Abstract
【解決手段】エレクトロルミネッセンス・デバイスは、カソードと、アノードと、その間にある発光層(LEL)とを備えるとともに、LELのカソード側にある電子輸送層(ETL)と、そのETLのカソード側に隣接した有機電子注入層(EIL)とをさらに備えていて、ETLが、2位と9位と10位に芳香族基を有するモノアントラセン化合物を含んでいる。
【選択図】なし
Description
R3とR4は、それぞれ独立にアリール基を表わし、そのアリール基は、構造式(C)に示したように、ジアリール置換されたアミノ基によって置換されている。
1,1-ビス(4-ジ-p-トリルアミノフェニル)シクロヘキサン(TAPC)
1,1-ビス(4-ジ-p-トリルアミノフェニル)-4-フェニルシクロヘキサン
4,4'-ビス(ジフェニルアミノ)クアドリフェニル
ビス(4-ジメチルアミノ-2-メチルフェニル)-フェニルメタン
N,N,N-トリ(p-トリル)アミン
4-(ジ-p-トリルアミノ)-4'-[4-(ジ-p-トリルアミノ)-スチリル]スチルベン
N,N,N',N'-テトラ-p-トリル-4,4'-ジアミノビフェニル
N,N,N',N'-テトラフェニル-4,4'-ジアミノビフェニル
N,N,N',N'-テトラ-1-ナフチル-4,4'-ジアミノビフェニル
N,N,N',N'-テトラ-2-ナフチル-4,4'-ジアミノビフェニル
N-フェニルカルバゾール
4,4'-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(1-ナフチル)-N-(2-ナフチル)アミノ]ビフェニル
4,4"-ビス[N-(1-ナフチル)-N-フェニルアミノ]p-テルフェニル
4,4'-ビス[N-(2-ナフチル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(3-アセナフテニル)-N-フェニルアミノ]ビフェニル
1,5-ビス[N-(1-ナフチル)-N-フェニルアミノ]ナフタレン
4,4'-ビス[N-(9-アントリル)-N-フェニルアミノ]ビフェニル
4,4"-ビス[N-(1-アントリル)-N-フェニルアミノ]-p-テルフェニル
4,4'-ビス[N-(2-フェナントリル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(8-フルオランテニル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(2-ピレニル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(2-ナフタセニル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(2-ペリレニル)-N-フェニルアミノ]ビフェニル
4,4'-ビス[N-(1-コロネニル)-N-フェニルアミノ]ビフェニル
2,6-ビス(ジ-p-トリルアミノ)ナフタレン
2,6-ビス[ジ-(1-ナフチル)アミノ]ナフタレン
2,6-ビス[N-(1-ナフチル)-N-(2-ナフチル)アミノ]ナフタレン
N,N,N',N'-テトラ(2-ナフチル)-4,4"-ジアミノ-p-テルフェニル
4,4'-ビス{N-フェニル-N-[4-(1-ナフチル)-フェニル]アミノ}ビフェニル
4,4'-ビス[N-フェニル-N-(2-ピレニル)アミノ]ビフェニル
2,6-ビス[N,N-ジ(2-ナフチル)アミノ]フルオレン
1,5-ビス[N-(1-ナフチル)-N-フェニルアミノ]ナフタレン
4,4',4"-トリス[(3-メチルフェニル)フェニルアミノ]トリフェニルアミン
CO-1:アルミニウムトリスオキシン[別名、トリス(8-キノリノラト)アルミニウム(III);Alq];
CO-2:マグネシウムビスオキシン[別名、ビス(8-キノリノラト)マグネシウム(II)];
CO-3:ビス[ベンゾ{f}-8-キノリノラト]亜鉛(II);
CO-4:ビス(2-メチル-8-キノリノラト)アルミニウム(III)-μ-オキソ-ビス(2-メチル-8-キノリノラト)アルミニウム(III);
CO-5:インジウムトリスオキシン[別名、トリス(8-キノリノラト)インジウム];
CO-6:アルミニウムトリス(5-メチルオキシン)[別名、トリス(5-メチル-8-キノリノラト)アルミニウム(III)];
CO-7:リチウムオキシン[別名、(8-キノリノラト)リチウム(I)];
CO-8:ガリウムオキシン[別名、トリス(8-キノリノラト)ガリウム(III)];
CO-9:ジルコニウムオキシン[別名、テトラ(8-キノリノラト)ジルコニウム(IV)]。
グループ1:水素、または炭素原子が1〜24個のアルキル;
グループ2:炭素原子が5〜20個のアリールまたは置換されたアリール
グループ3:アントラセニル、ピレニル、ペリレニルの縮合芳香族環を完成させるのに必要な4〜24個の炭素原子;
グループ4:フリル、チエニル、ピリジル、キノリニル、または他の複素環系の縮合ヘテロ芳香族環を完成させるのに必要な、5〜24個の炭素原子からなるヘテロアリールまたは置換されたヘテロアリール;
グループ5:炭素原子が1〜24個のアルコキシルアミノ、アルキルアミノ、アリールアミノ;
グループ6:フッ素またはシアノ。
グループ1:水素、または炭素原子が1〜24個のアルキル;
グループ2:炭素原子が5〜20個のアリールまたは置換されたアリール
グループ3:アントラセニル、ピレニル、ペリレニルの縮合芳香族環を完成させるのに必要な4〜24個の炭素原子;
グループ4:フリル、チエニル、ピリジル、キノリニル、または他の複素環系の縮合ヘテロ芳香族環を完成させるのに必要な、5〜24個の炭素原子からなるヘテロアリールまたは置換されたヘテロアリール;
グループ5:炭素原子が1〜24個のアルコキシルアミノ、アルキルアミノ、アリールアミノ;
グループ6:フッ素またはシアノ。
電気化学的酸化還元電位と推定エネルギー・レベル
可逆的プロセスまたは準可逆的プロセスに関してSCEを基準とした正式な還元電位:
E0/ 還元 = (Epa + Epc)/2
E0/ 酸化 = (Epa + Epc)/2
Fcを基準とした正式な還元電位:
Fcに対するE0/ 還元= (SCEに対するE0' 還元 ) - EFc
Fcに対するE0/ 酸化= (SCEに対するE0' 酸化 ) - EFc
ただしEFcはフェロセンの酸化電位E酸化である。
LUMO値とHOMO値の予想される下限:
LUMO = HOMOFc - (Fcに対するE0/ 還元 )
HOMO = HOMOFc - (Fcに対するE0/ 酸化 )
ただしHOMOFc(フェロセンの最高被占軌道)は-4.8eVである。
デバイス1-1〜1-12の製造
デバイス2-1〜2-11の製造
デバイス3-1〜3-12の製造
デバイス4-1〜4-7の製造
デバイス5-1〜5-6の製造
デバイス6-1〜6-9の製造
デバイス7-1〜7-12の製造
デバイス8-1〜8-5の製造
デバイス9-1〜9-5の製造
103 アノード
105 正孔注入層(HIL)
107 正孔輸送層(HTL)
109 発光層(LEL)
110 電子輸送層(ETL)
111 電子注入層(EIL)
112 第2の電子注入層
113 カソード
150 電圧/電流源
160 導電体
Claims (12)
- カソードと、アノードと、その間にある発光層(LEL)とを備えるとともに、LELのカソード側にある電子輸送層(ETL)と、そのETLのカソード側に隣接した有機電子注入層(EIL)とをさらに備えていて、上記ETLが、2位と9位と10位に芳香族基を有するモノアントラセン化合物を含むエレクトロルミネッセンス・デバイス。
- 上記ETLが、ナフチル基またはビフェニル基で9位が置換され、独立に選択されたナフチル基またはビフェニル基で10位が置換されたモノアントラセン化合物を含む、請求項1に記載のデバイス。
- 上記ETLが、2個以下の縮合環を有するアリール基で2位が置換されたモノアントラセン化合物を含む、請求項1に記載のデバイス。
- 上記ETLが、独立に選択された芳香族基を2位と6位と9位と10位に有するモノアントラセン化合物を含む、請求項1に記載のデバイス。
- 上記モノアントラセン化合物と上記複素環化合物のLUMO値の差が0.2eV以下である、請求項1に記載のデバイス。
- 上記電子注入層が、上記モノアントラセン化合物のLUMO値と等しいかよりプラスのLUMO値を持つ複素環化合物を含む、請求項6に記載のデバイス。
- 上記電子注入層が、(a)少なくとも3つの縮合芳香族環を含む少なくとも1つの置換基を有する1,10-フェナントロリンの誘導体、(b)ベンゾイミダゾールの誘導体、(c)8-キノレートの金属錯体又は(d)2,2-ビピリジル誘導体を含む、請求項1に記載のデバイス。
- 上記LELが、上記モノアントラセン化合物のLUMO値との差が0.2eV以下であるLUMO値を持つホスト材料を含む、請求項1に記載のデバイス。
- 上記LELが、青色、青-緑色、緑色いずれかの光を出す、請求項1に記載のデバイス。
- 上記LELが、2位と9位と10位に芳香族基を有するアントラセン材料を含む、請求項1に記載のデバイス。
- 上記LELが、ホウ素含有発光材料、またはスチリルアレン誘導体含有発光材料を含む、請求項1に記載のデバイス。
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KR20230116914A (ko) | 2020-12-07 | 2023-08-04 | 오티아이 루미오닉스 인크. | 핵 생성 억제 코팅 및 하부 금속 코팅을 사용한 전도성 증착 층의 패턴화 |
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TW200624533A (en) * | 2004-10-29 | 2006-07-16 | Sony Corp | Organic electroluminescence device and display apparatus |
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JP2018534768A (ja) * | 2015-09-28 | 2018-11-22 | ノヴァレッド ゲーエムベーハー | 有機elデバイス |
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WO2007130263A1 (en) | 2007-11-15 |
TW200803616A (en) | 2008-01-01 |
JP2009535815A (ja) | 2009-10-01 |
US7733009B2 (en) | 2010-06-08 |
TWI387392B (zh) | 2013-02-21 |
DE602007002892D1 (de) | 2009-12-03 |
EP2013314A1 (en) | 2009-01-14 |
US20070252521A1 (en) | 2007-11-01 |
KR20090005079A (ko) | 2009-01-12 |
JP5529532B2 (ja) | 2014-06-25 |
EP2013314B1 (en) | 2009-10-21 |
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