JP6095390B2 - 有機発光素子及び表示装置 - Google Patents
有機発光素子及び表示装置 Download PDFInfo
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- JP6095390B2 JP6095390B2 JP2013021048A JP2013021048A JP6095390B2 JP 6095390 B2 JP6095390 B2 JP 6095390B2 JP 2013021048 A JP2013021048 A JP 2013021048A JP 2013021048 A JP2013021048 A JP 2013021048A JP 6095390 B2 JP6095390 B2 JP 6095390B2
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- emitting device
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- -1 metal complex compound Chemical class 0.000 claims description 105
- 239000000463 material Substances 0.000 claims description 96
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- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 229910052751 metal Inorganic materials 0.000 claims description 35
- 239000002184 metal Substances 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 150000002894 organic compounds Chemical class 0.000 claims description 30
- 125000003277 amino group Chemical group 0.000 claims description 26
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000011777 magnesium Substances 0.000 claims description 16
- 239000011701 zinc Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
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Images
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Description
前記有機化合物層が、下記一般式[1]に示されるイリジウム錯体と、下記一般式[5]に示される金属錯体と、を有することを特徴とする。
ML2 [5]
(式[5]において、Mは、ベリリウム、マグネシウム及び亜鉛から選ばれる2価の金属原子である。Lは、二座配位子を表す。Mがベリリウム又はマグネシウムの場合、部分構造MLは、下記一般式[6]乃至[11]に示される構造のいずれかである。またMが亜鉛の場合、部分構造MLは、下記一般式[7]乃至[11]の示される構造のいずれかである。
本発明の有機発光素子は、互いに対向し合う一対の電極である陽極と陰極と、これら一対の電極の間に配置される有機化合物層とを少なくとも有する発光素子である。そして本発明の有機発光素子は、有機化合物層に、下記一般式[1]で示されるイリジウム錯体と下記一般式[5]で示される金属錯体化合物とを有する。
(1)陽極/発光層/陰極
(2)陽極/正孔輸送層/発光層/電子輸送層/陰極
(3)陽極/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(4)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極
(5)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(6)陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極
次に、本発明の有機発光素子の構成材料の一つであるイリジウム錯体について説明する。本発明の有機発光素子の構成材料の一つであるイリジウム錯体は、下記一般式[1]で示される化合物である。
次に、本発明の有機発光素子に、発光層のホストとして用いられる金属錯体化合物について説明する。本発明の有機発光素子に含まれるホストとなる金属錯体化合物は、具体的には、下記一般式[5]で示される化合物である。
ML2 [5]
本発明の有機発光素子を構成する有機化合物層(特に、発光層)は、一般式[1]のイリジウム錯体と、一般式[5]の金属錯体と、を少なくとも有している。式[1]のイリジウム錯体は、少なくとも1つのアリールナフト[2,1−f]イソキノリン配位子がイリジウム金属に配位している有機金属錯体、即ち、niq系Ir錯体である。ここでniq系Ir錯体は、特許文献1に記載の通り、高い発光量子収率を有している赤色発光性の燐光発光材料である。ここで赤色発光とは、発光ピーク波長が580nm以上650nm以下、即ち、最低三重項励起準位(T1)が1.9eV以上2.1eV以下の範囲にある発光のことをいう。従って、niq系Ir錯体をゲストとして発光層に含ませることによって、有機発光素子の発光効率が非常に高くなる。
[項目1]発光材料とホストとの三重項状態の励起エネルギー(T1)の関係
[項目2]発光材料とホストとのバンドギャップ(S1)の関係
[項目3]発光材料とホストとのHOMO−LUMOの関係
[項目4]発光材料の発光効率
以下に、一般式[1]で定義されるイリジウム錯体の具体的な構造式を例示する。
以下に、ホストとして用いられる金属錯体化合物の具体的な構造式を例示する。
以上説明したように、本発明の有機発光素子は、有機化合物層(好ましくは、発光層)に、一般式[1]のイリジウム錯体及び一般式[5]の金属錯体化合物が少なくとも含まれている。ただし、本発明では、これら化合物以外にも、必要に応じて従来公知の低分子系及び高分子系の材料を使用することができる。より具体的には正孔注入輸送性材料、発光アシスト材料、あるいは電子注入輸送性材料等を上記イリジウム錯体及び上記金属錯体化合物と一緒に使用することができる。
本発明の有機発光素子は、表示装置や照明装置の構成部材として用いることができる。他にも、電子写真方式の画像形成装置の露光光源や液晶表示装置のバックライト、白色光源にカラーフィルターを有する発光装置等の用途がある。カラーフィルターは例えば赤、緑、青の3つの色が透過するフィルターが挙げられる。
特許文献1、非特許文献1乃至7等を参考にして、下記に示す合成スキームにより、例示化合物KK−01及び化合物E2を合成した。
(1)化合物1−1を出発原料とする、配位子となる有機化合物(化合物1−5)の合成
(2)クロロ架橋錯体(化合物1−6)の合成
(3)補助配位子を有する錯体(例示化合物KK−01)の合成
(4)3配位錯体(化合物E2)の合成
合成例1において、合成原料B1−1の代わりに下記に示される化合物を使用する以外は、合成例1と同様の合成方法により、例示化合物KK−04を合成した。
合成例1において、合成原料B1−2の代わりに下記に示される化合物を使用する以外は、合成例1と同様の合成方法により、例示化合物KK−05を合成した。
合成例2において、合成原料B1−2の代わりに下記に示される化合物を使用する以外は、合成例2と同様の合成方法により、例示化合物KK−13を合成した。
合成例1において、合成原料B1−3の代わりに下記に示される化合物を使用する以外は、合成例1と同様の合成方法により、例示化合物KK−28を合成した。
合成例5において、合成原料B1−1の代わりに下記に示される化合物を使用する以外は、合成例5と同様の合成方法により、例示化合物KK−31を合成した。
合成例5において、合成原料B1−2の代わりに下記に示される化合物を使用する以外は、合成例5と同様の合成方法により、例示化合物KK−32を合成した。
上記合成例1と同様の文献を参考にして、下記合成スキームにてKK−03を合成した。
合成例8において、合成原料B2−1の代わりに下記に示される化合物を使用する以外は、合成例5と同様の合成方法により、例示化合物KK−12を合成した。
合成例8において、合成原料B2−3の代わりに下記に示される化合物を使用する以外は、合成例5と同様の合成方法により、例示化合物KK−30を合成した。
合成例10において、合成原料B2−2の代わりに下記に示される化合物を使用する以外は、合成例5と同様の合成方法により、例示化合物KK−36を合成した。
下記に示す合成スキーム、具体的には、キノリン−8−オールを出発原料とするメタノール中における錯化反応を行うことにより、例示化合物H101、H201及びH301をそれぞれ合成した。
合成例12において、合成原料を、キノリン−8−オールから下記表2に示す化合物に変更する以外は、合成例12と同様の合成方法により金属錯体を合成した。得られた金属錯体について、合成例12と同様の方法により構造確認を行った。結果を表6に示す。
合成例13において、合成原料を、キノリン−8−オールから下記表3又は表4に示す化合物に変更する以外は、合成例13と同様の合成方法により金属錯体を合成した。得られた金属錯体について、合成例13と同様の方法により構造確認を行った。結果を表6に示す。
合成例14において、合成原料を、キノリン−8−オールから下記表5に示す化合物に変更する以外は、合成例14と同様の合成方法により金属錯体を合成した。得られた金属錯体について、合成例14と同様の方法により構造確認を行った。結果を表6に示す。
本実施例では、基板上に、陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極がこの順に設けられた構成の有機発光素子を以下に示す方法で作製した。
実施例1において、正孔輸送層(HTL)、電子阻止層(EBL)、発光層ホスト(HOST)、発光層ゲスト(GUEST)、正孔阻止層(HBL)及び電子輸送層(ETL)として用いた化合物を、下記表8に示される化合物に適宜変更した。これを除いては、実施例1と同様の方法により有機発光素子を作製した。得られた素子について実施例1と同様に素子の特性を測定・評価した。測定の結果を表8に示す。
本実施例では、基板上に、陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極がこの順に設けられた構成の有機発光素子を作製した。尚、本実施例において、発光層にはアシスト材料が含まれている。
実施例23において、正孔輸送層(HTL)、電子阻止層(EBL)、発光層ホスト(HOST)、発光層アシスト(ASSIST)、発光層ゲスト(GUEST)、正孔阻止層(HBL)及び電子輸送層(ETL)に用いた化合物を、表10の通りに変更した。これを除いては、実施例23と同様の方法により有機発光素子を作製した。得られた素子について実施例23と同様に素子の特性を測定・評価した。測定の結果を表10に示す。
Claims (13)
- 一対の電極と、前記一対の電極の間に配置される有機化合物層と、を有し、
前記有機化合物層が、下記一般式[1]に示されるイリジウム錯体と、下記一般式[5]に示される金属錯体と、を有することを特徴とする、有機発光素子。
ML2 [5]
(式[5]において、Mは、ベリリウム、マグネシウム及び亜鉛から選ばれる2価の金属原子である。Lは、二座配位子を表す。Mがベリリウム又はマグネシウムの場合、部分構造MLは、下記一般式[6]乃至[11]に示される構造のいずれかである。またMが亜鉛の場合、部分構造MLは、下記一般式[7]乃至[11]の示される構造のいずれかである。
- 前記mが2であり、前記nが1であることを特徴とする、請求項1又は2に記載の有機発光素子。
- 前記有機化合物層が、ホストとゲストとを有する発光層であり、
前記ゲストが、前記一般式[1]に示されるイリジウム錯体であり、
前記ホストが、前記一般式[5]に示される金属錯体化合物であることを特徴とする、請求項1乃至4のいずれか一項に記載の有機発光素子。 - 前記有機化合物層が、前記ホスト及び前記ゲストとは異なるアシスト材料をさらに有することを特徴とする、請求項5に記載の有機発光素子。
- 前記アシスト材料がイリジウム錯体であることを特徴とする、請求項6に記載の有機発光素子。
- 赤色発光することを特徴とする、請求項1乃至7のいずれか一項に記載の有機発光素子。
- 複数の画素を有し、
前記画素が、請求項1乃至8の何れか一項に記載の有機発光素子と、前記有機発光素子に接続されている能動素子と、を有することを特徴とする、表示装置。 - 画像を表示するための表示部と、
画像情報を入力するための入力部と、を有し、
前記表示部が、請求項9に記載の表示装置であることを特徴とする、情報処理装置。 - 請求項1乃至8の何れか一項に記載の有機発光素子と、
前記有機発光素子に接続されているAC/DCコンバーター回路と、を有することを特徴とする照明装置。 - 感光体と、
前記感光体の表面を帯電させる帯電手段と、
前記感光体を露光して静電潜像を形成するための露光手段と、
前記感光体の表面に形成された静電潜像を現像するための現像手段と、を有する画像形成装置であって、
前記露光手段が、請求項1乃至8の何れか一項に記載の有機発光素子を有することを
特徴とする画像形成装置。 - 感光体を露光するための露光装置であって、
前記露光装置が、請求項1乃至8のいずれか一項に記載の有機発光素子を有し、
前記有機発光素子が、所定の方向に沿って列を形成して配置されていることを特徴とする、露光装置。
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JP6166557B2 (ja) * | 2012-04-20 | 2017-07-19 | 株式会社半導体エネルギー研究所 | 燐光性有機金属イリジウム錯体、発光素子、発光装置、電子機器、および照明装置 |
JP6157125B2 (ja) * | 2013-01-22 | 2017-07-05 | キヤノン株式会社 | イリジウム錯体およびそれを有する有機発光素子 |
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EP2954570A1 (en) | 2015-12-16 |
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WO2014123239A1 (en) | 2014-08-14 |
EP2954570A4 (en) | 2016-11-16 |
US9601704B2 (en) | 2017-03-21 |
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