JP2018181916A - 発光素子、発光装置、電子機器及び照明装置 - Google Patents
発光素子、発光装置、電子機器及び照明装置 Download PDFInfo
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- JP2018181916A JP2018181916A JP2017074617A JP2017074617A JP2018181916A JP 2018181916 A JP2018181916 A JP 2018181916A JP 2017074617 A JP2017074617 A JP 2017074617A JP 2017074617 A JP2017074617 A JP 2017074617A JP 2018181916 A JP2018181916 A JP 2018181916A
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Abstract
Description
有機EL素子の発光層は、ホスト材料であるキャリア輸送材料と、ゲスト材料である発光材料とを共蒸着することで混合しながら成膜する方法が主流となっている。共蒸着行うためには、蒸着室の中に複数の蒸着源を備える必要がある。また、コンタミ防止の観点から長大な製造装置が必要となり、莫大な初期投資必要であることから、新規企業の参入に大きな障壁となっている。また、煩雑で冗長な製造工程は、製品コストの増加につながっていた。
トラセン(略称:BPT)、2−(2−{2−[4−(ジメチルアミノ)フェニル]エテニル}−6−メチル−4H−ピラン−4−イリデン)プロパンジニトリル(略称:DCM1)、2−{2−メチル−6−[2−(2,3,6,7−テトラヒドロ−1H,5H−ベンゾ[ij]キノリジン−9−イル)エテニル]−4H−ピラン−4−イリデン}プロパンジニトリル(略称:DCM2)、N,N,N’,N’−テトラキス(4−メチルフェニル)テトラセン−5,11−ジアミン(略称:p−mPhTD)、7,14−ジフェニル−N,N,N’,N’−テトラキス(4−メチルフェニル)アセナフト[1,2−a]フルオランテン−3,10−ジアミン(略称:p−mPhAFD)、2−{2−イソプロピル−6−[2−(1,1,7,7−テトラメチル−2,3,6,7−テトラヒドロ−1H,5H−ベンゾ[ij]キノリジン−9−イル)エテニル]−4H−ピラン−4−イリデン}プロパンジニトリル(略称:DCJTI)、2−{2−tert−ブチル−6−[2−(1,1,7,7−テトラメチル−2,3,6,7−テトラヒドロ−1H,5H−ベンゾ[ij]キノリジン−9−イル)エテニル]−4H−ピラン−4−イリデン}プロパンジニトリル(略称:DCJTB)、2−(2,6−ビス{2−[4−(ジメチルアミノ)フェニル]エテニル}−4H−ピラン−4−イリデン)プロパンジニトリル(略称:BisDCM)、2−{2,6−ビス[2−(8−メトキシ−1,1,7,7−テトラメチル−2,3,6,7−テトラヒドロ−1H,5H−ベンゾ[ij]キノリジン−9−イル)エテニル]−4H−ピラン−4−イリデン}プロパンジニトリル(略称:BisDCJTM)、5,10,15,20−テトラフェニルビスベンゾ[5,6]インデノ[1,2,3−cd:1’,2’,3’−lm]ペリレンなどの蛍光性化合物が挙げられる。
本実施の形態では、実施の形態1に記載の発光素子を用いた発光装置について説明する。
本発明の一態様である照明装置を図9を参照しながら説明する。図9(B)は照明装置の上面図、図9(A)は図9(B)におけるe−f断面図である。
本発明の一態様である電子機器の例について説明する。電子機器として、例えば、テレビジョン装置(テレビ、またはテレビジョン受信機ともいう)、コンピュータ用などのモニタ、デジタルカメラ、デジタルビデオカメラ、デジタルフォトフレーム、携帯電話機(携帯電話、携帯電話装置ともいう)、携帯型ゲーム機、携帯情報端末、音響再生装置、パチンコ機などの大型ゲーム機などが挙げられる。これらの電子機器の具体例を以下に示す。
≪合成例1≫
本実施例では、実施の形態1において説明したキャリア輸送性を有する第1の骨格と、発光性を有する第2の骨格を一分子内に同時に有する有機化合物である[2−{(9H−カルバゾール−9−イル)−2−ピリジニル−κN}フェニル−κC]ビス[2−(2−ピリジニル−κN)フェニル−κC]イリジウム(III)(略称:[Ir(ppy)2(Czppy)])の合成例を具体的に例示する。[Ir(ppy)2(Czppy)]はイリジウムを中心金属とし、正孔輸送性を有する骨格第1の骨格と、発光性を有する第2の骨格と、を有する配位子を有する有機金属錯体である。[Ir(ppy)2(Czppy)]の構造式を以下に示す。
まず、2,4−ジクロロピリジン12g、フェニルボロン酸9.9g、炭酸カリウム34g、DME400mL、水240mLを、還流管を付けた三口フラスコに入れ、フラスコ内を窒素置換した。さらにテトラキス(トリフェニルホスフィン)パラジウム(0)0.94gを加え、マイクロ波(2.45GHz、400W)を2時間照射した。反応後、酢酸エチルによる抽出を行った。その後、ジクロロメタンを展開溶媒としたシリカゲルカラムクロマトグライフィーにて精製することにより、目的物を12g(収率80%、黄色油状物)得た。ステップ1の合成スキームを下記(a−1)に示す。
次に、上記ステップ1で得た4−クロロ−2−フェニルピリジン12g、9H−カルバゾール13g、ナトリウム−tert−ブトキシド(略称:tert−BuONa)11gを、還流管を付けた三口フラスコに入れ、フラスコ内を窒素置換した。さらにトルエン280mL、トリ−tert−ブチルホスフィン1.3g、トリス(ジベンジリデンアセトン)ジパラジウム(0)(略称:Pd2(dba)3)3.0gを加え、120℃にて5時間加熱攪拌した。得られた反応物をろ過し、ろ液の溶媒を留去し、ジクロロメタン:ヘキサン=1:1を展開溶媒としたシリカゲルカラムクロマトグライフィーにて精製することにより、目的物を11g(収率53%、黄色油状物)得た。ステップ2の合成スキームを下記(a−2)に示す。
次に、[Ir(ppy)2Cl]2(略称)2.8gとジクロロメタン200mLを三口フラスコに入れフラスコ内を窒素置換した。ここに、銀トリフラート2.0gとメタノール40mLの混合液を滴下し、室温にて20時間攪拌した。得られた混合物を、セライトを通した後、濃縮し、固体を得た。
≪合成例2≫
本実施例では、実施の形態1において説明したキャリア輸送性を有する第1の骨格と、発光性を有する第2の骨格を一分子内に同時に有する有機化合物であるビス[2−{4−(9H−カルバゾール−9−イル)−2−ピリジニル−κN}フェニル−κC][2−(2−ピリジニル−κN)フェニル−κC]イリジウム(III)(略称:[Ir(ppy)(Czppy)2])の合成例を具体的に例示する。[Ir(ppy)(Czppy)2]はイリジウムを中心金属とし、正孔輸送性を有する骨格第1の骨格と、発光性を有する第2の骨格と、を有する配位子を有する有機金属錯体である。[Ir(ppy)(Czppy)2]の構造式を以下に示す。
まず、HCzppy(略称)6.1g、塩化イリジウム(III)水和物2.9g、2−エトキシエタノール90mL、水30mLを、還流管を付けた丸底フラスコに入れ、アルゴンバブリングをしながらマイクロ波(2.45GHz、200W)を2時間照射した。得られた混合物をろ過し、メタノールにて洗浄することにより、目的物を6.3g(収率76%、黄色固体)得た。また、ステップ1の合成スキームを下記(b−1)に示す。
次に、上記ステップ1で得た[Ir(Czppy)2Cl]2、4.3gとジクロロメタン(略称:DCM)250mLを三口フラスコに入れフラスコ内を窒素置換した。ここに、銀トリフラート1.9gとイソプロパノール40mLの混合液を滴下し、室温にて20時間攪拌した。得られた混合物を、セライトを通した後、濃縮し、固体を得た。この固体に2−フェニルピリジン(略称:Hppy)1.6g、2−エトキシエタノール50mL、N,N−ジメチルホルムアミド(略称:DMF)50mLを加え、窒素雰囲気下にて17時間還流させた。
≪合成例3≫
本実施例では、実施の形態1において説明したキャリア輸送性を有する第1の骨格と、発光性を有する第2の骨格を一分子内に同時に有する有機化合物であるビス{2−[6−(9H−カルバゾール−9−イル)−4−ピリミジニル−κN3]フェニル−κC}−{2−[2−ピリジニル−κN]フェニル−κC}イリジウム(III)(略称:[Ir(czppm)2(ppy)])の合成例を具体的に例示する。[Ir(czppm)2(ppy)]はイリジウムを中心金属とし、正孔輸送性を有する骨格第1の骨格と、発光性を有する第2の骨格と、を有する配位子を有する有機金属錯体である。[Ir(czppm)2(ppy)]の構造式を以下に示す。
水素化ナトリウム(60% in mineral oil)0.053gとドライN,N−ジメチルホルムアミド(略称:dryDMF)30mLを、三口フラスコに入れ、内部を窒素置換した。ここにカルバゾール1.76gとdryDMF30mLを加え、室温で1時間攪拌した。その後、4−クロロ−6−フェニルピリミジン1.76gとdryDMF30mLを加え、室温で4時間攪拌し、反応させた。反応後、得られた溶液を水に加え、吸引ろ過し、固体を得た。得られた固体を、ジクロロメタンを展開溶媒とするフラッシュカラムクロマトグラフィーにより精製し、目的のピリミジン誘導体Hczppmを得た(白色粉末、収率62%)。ステップ1の合成スキームを以下に示す。
2−エトキシエタノール30mLと水10mL、2−フェニルピリジン(略称:Hppy)3.88g、塩化イリジウム水和物(IrCl3・H2O)(フルヤ金属社製)3.49gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を2時間照射し、反応させた。反応後、得られた混合物をメタノールを用いて吸引ろ過、洗浄し、複核錯体[Ir(ppy)2Cl]2 を得た(黄色固体、収率59%)。ステップ2の合成スキームを以下に示す。
上記ステップ2で得た複核錯体[Ir(ppy)2Cl]2 3.69gとジクロロメタン390mLを、遮光した三口フラスコに入れ、フラスコ内を窒素置換した。ここに、メタノール180mLで溶かしたトリフルオロメタンスルホン酸銀2.27gを滴下し、室温で24時間撹拌した。得られた混合物をセライトで積層したろ過補助剤を通して濾過した後、ろ液を濃縮し、固体を得た。続いて、得られた固体とHczppm3.90g、エタノール40mLを、還流管を付けた三口フラスコに入れ、フラスコ内を窒素置換した。90℃で48時間加熱した後、得られた混合物を吸引ろ過した。得られた残差を、ヘキサン:酢酸エチル=6:1を展開溶媒とするシリカゲルカラムクロマトグラフィーにより精製した後、ジクロロメタンとメタノールの混合溶媒にて再結晶することにより、本発明の一態様の発光素子用材料である[Ir(czppm)2(ppy)]を黄橙色粉末として得た(収率6%)。ステップ3の合成スキームを以下に示す。
102 陰極
103 EL層
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
116 電荷発生層
117 P型層
118 電子リレー層
119 電子注入バッファ層
400 基板
401 陽極
403 EL層
404 陰極
405 シール材
406 シール材
407 封止基板
412 パッド
420 ICチップ
501 陽極
502 陰極
503 EL層
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 駆動回路部(ソース線駆動回路)
602 画素部
603 駆動回路部(ゲート線駆動回路)
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用FET
612 電流制御用FET
613 陽極
614 絶縁物
616 EL層
617 陰極
618 発光素子
730 絶縁膜
770 平坦化絶縁膜
772 導電膜
782 発光素子
783 液滴吐出装置
784 液滴
785 層
786 EL層
788 導電膜
901 筐体
902 液晶層
903 バックライトユニット
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 EL層
956 電極
1001 基板
1002 下地絶縁膜
1003 ゲート絶縁膜
1006 ゲート電極
1007 ゲート電極
1008 ゲート電極
1020 第1の層間絶縁膜
1021 第2の層間絶縁膜
1022 電極
1024W 陽極
1024R 陽極
1024G 陽極
1024B 陽極
1025 隔壁
1028 EL層
1029 陰極
1031 封止基板
1032 シール材
1033 透明な基材
1034R 赤色の着色層
1034G 緑色の着色層
1034B 青色の着色層
1035 ブラックマトリクス
1037 第3の層間絶縁膜
1040 画素部
1041 駆動回路部
1042 周辺部
1400 液滴吐出装置
1402 基板
1403 液滴吐出手段
1404 撮像手段
1405 ヘッド
1406 点線
1407 制御手段
1408 記憶媒体
1409 画像処理手段
1410 コンピュータ
1411 マーカー
1412 ヘッド
1413 材料供給源
1414 材料供給源
1415 材料供給源
1416 ヘッド
2001 筐体
2002 光源
3001 照明装置
5000 表示領域
5001 表示領域
5002 表示領域
5003 表示領域
5004 表示領域
5005 表示領域
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 ポインティングデバイス
7210 第2の表示部
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
9033 留め具
9034 スイッチ
9035 電源スイッチ
9036 スイッチ
9038 操作スイッチ
9310 携帯情報端末
9311 表示パネル
9312 表示領域
9313 ヒンジ
9315 筐体
9630 筐体
9631 表示部
9631a 表示部
9631b 表示部
9632a タッチパネル領域
9632b タッチパネル領域
9633 太陽電池
9634 充放電制御回路
9635 バッテリー
9636 DCDCコンバータ
9637 操作キー
9638 コンバータ
9639 ボタン
Claims (27)
- 陽極と、
陰極と、
前記陽極および前記陰極の間に位置するEL層とを有し、
前記EL層は正孔輸送層と、前記正孔輸送層と接する発光層とを有し、
前記発光層は、第1の物質を有し、
前記第1の物質は、キャリア輸送性を有する第1の骨格と発光性を有する第2の骨格とを一分子内に有し、且つ分子量が3000以下である有機化合物であり、
前記正孔輸送層は正孔輸送性を有する高分子化合物を有する発光素子。 - 請求項1において、前記第1の骨格が正孔輸送性を有する骨格である発光素子。
- 請求項2において、前記第1の骨格が前記有機化合物のHOMOを有する骨格である発光素子。
- 請求項1において、前記第1の骨格が電子輸送性を有する骨格である発光素子。
- 請求項4において、前記第1の骨格が前記有機化合物のLUMOを有する骨格である発光素子。
- 請求項1乃至請求項5のいずれか一項において、前記第1の骨格が前記第2の骨格に直接結合している発光素子。
- 請求項1乃至請求項5のいずれか一項において、前記第1の骨格と前記第2の骨格がメタフェニレン基またはビフェニル−3,3’−ジイル基で連結されている発光素子。
- 陽極と、
陰極と、
前記陽極と前記陰極との間に位置するEL層とを有し、
前記EL層は正孔輸送層と前記正孔輸送層に接する発光層を有し、
前記EL層は第1の物質を有し、
前記第1の物質は、正孔輸送性を有する第1の骨格と、電子輸送性を有する第2の骨格と、発光性を有する第3の骨格とを有し、且つ分子量3000以下の有機化合物であり、
前記正孔輸送層が正孔輸送性を有する高分子化合物を有する発光素子。 - 請求項8において、前記第1の骨格が前記有機化合物のHOMOを有する骨格である発光素子。
- 請求項8または請求項9において、前記第2の骨格が前記有機化合物のLUMOを有する発光素子。
- 請求項8乃至請求項10のいずれか一項において、前記第1の骨格および/または前記第2の骨格が、前記第3の骨格に直接結合している発光素子。
- 請求項8乃至請求項10のいずれか一項において、前記第1の骨格および/または前記第2の骨格が、前記第3の骨格とメタフェニレン基もしくはビフェニル−3,3’−ジイル基で連結されている発光素子。
- 請求項1乃至請求項12のいずれか一項において、
前記有機化合物が蛍光を発する発光素子。 - 請求項1乃至請求項12のいずれか一項において、
前記有機化合物が遅延蛍光を発する発光素子。 - 請求項1乃至請求項12のいずれか一項において、
前記有機化合物がりん光を発する発光素子。 - 請求項15において、前記有機化合物がさらに中心金属を有する有機金属錯体である発光素子。
- 請求項16において、前記中心金属がイリジウムである発光素子。
- 請求項16または17において、前記有機金属錯体は少なくとも2つの異なる配位子を有し、一方の配位子は発光性の骨格を有し、他方の配位子は正孔輸送性の骨格を有する発光素子。
- 請求項16または17において、前記有機金属錯体は少なくとも2つの異なる配位子を有し、一方の配位子は発光性の骨格を有し、他方の配位子は電子輸送性の骨格を有する発光素子。
- 請求項16または17において、前記有機金属錯体は少なくとも2つの異なる配位子を有し、一方の配位子は正孔輸送性の骨格を有し、他方の配位子は電子輸送性の骨格を有し、前記2つの異なる配位子の少なくともいずれか一方は発光性の骨格をさらに有する発光素子。
- 請求項1乃至請求項20のいずれか一項において、
前記有機化合物または前記有機金属錯体の分子量が1300以下である発光素子。 - 請求項1乃至請求項21のいずれか一項において、
前記発光層および/または前記正孔輸送層が湿式法により形成された発光素子。 - 請求項1乃至請求項21のいずれか一項において、
前記発光層および/または前記正孔輸送層が印刷法により形成された発光素子。 - 請求項1乃至請求項23のいずれか一項において、
前記高分子化合物がポリ[N,N’−ビス(4−ブチルフェニル)−N,N’−ビス(フェニル)ベンジジン]またはポリ(9,9−ジオクチルーフルオレンーalt−N−(4−ブチルフェニル)−ジフェニルアミンである発光素子。 - 請求項1乃至請求項24のいずれか一項に記載の発光素子と、トランジスタ、または、基板とを有する発光装置。
- 請求項25に記載の発光装置と筐体とを有する照明装置。
- 請求項25に記載の発光装置と、センサと、操作ボタンと、スピーカまたはマイクと、を有する電子機器。
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