JP6400113B2 - 有機エレクトロルミネセンス材料、有機エレクトロルミネセンス材料の製作方法及び有機エレクトロルミネセンス素子 - Google Patents
有機エレクトロルミネセンス材料、有機エレクトロルミネセンス材料の製作方法及び有機エレクトロルミネセンス素子 Download PDFInfo
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Description
R 1 〜R 3 は独立に、C6〜C40の1つまたは複数の置換基R含有のまたは未置換のアリール基、C6〜C40のアリールラジカル基、C3〜C40の1つの置換基R含有のまたは未置換の1つまたは複数のヘテロ原子含有のアリール基を表し、前記へテロ原子がO、S、Nで、前記置換基Rがハロゲン、シアン基、ニトロ基、アミノ基、C1〜C4アルキル基、C1〜C4アルコキシ基である。
好ましくは、R 1 が、C6〜C20の1つの置換基R含有のまたは未置換の1つまたは複数のヘテロ原子含有の五員または六員ヘテロアリール基、C10〜C20の1つの置換基R含有のまたは未置換の縮合芳香族環基、C6〜C30の1つまたは複数の置換基R含有のまたは未置換のフェニル基から選ばれ、前記置換基Rがハロゲン、シアン基、ニトロ基、アミノ基、C1〜C4アルキル基、C1〜C4アルコキシ基で、前記へテロ原子がO、S、Nである。
を製作するステップ(1)、
さらにR1−CNと、窒素ガスの保護下で、250〜300℃にて40〜50h反応させて製作するステップ(2)を含む反応することによって製作される。
を70〜100℃下で還流して製作する。
アセナフテンキノン (84 g,0.46 mol)、 1,3−ジフェニルアセトン (72.8 g,0.34 mol)、 600mlエタノール、56g水酸化カリウムを4つ口フラスコに加えて撹拌し始め、窒素ガスを注入し、2h還流する。室温まで冷却し、ろ過を行い、ろ過ケーキをエタノールで2回リンスし、130g黒色固体を得、収率が91%である。
中間体3 (3.56 g, 10 mmol)及び中間体4 (4.69g, 40 mmol)を窒素ガス下で混合し且つ48h加熱還流する(外部温度280 oC)。得た褐色溶液を冷却し、褐色固体を得、石油エーテルをリンス液としシリカゲルカラムを通過した後それをジクロロメタン - アセトンにて結晶させてANP 8の白色結晶を得る。0.23gの製品を得、収率が5%である。ESI−MS m/s 計算値 C34H23N:445.18、実測値[M+]: 446.18。図2を参照。
まず、透明導電ITOガラス(陽極20の有するガラス基板10)を順に洗浄剤溶液及び脱イオン水、エタノール、アセトン、脱イオン水によって洗浄を行う。さらに酸素プラズマを使用して30s処理し、その後プラズマにより処理されたCFxで処理を行う。
その後、ITOに75nm厚さのNPBを蒸着して正孔注入層30とする。
その後、TCTAを蒸着し、10nm厚さの正孔輸送層(正孔伝送層)40を形成する。
その後、正孔輸送層に20nm厚さのANP 34+1%化合物1(構造は以下の式を参照する)を蒸着して発光層50とする。
その後、発光層に20nm厚さの化合物BPhenを蒸着して電子輸送層(電子伝送層)60とする。
最後に、1nmのLIFを蒸着して電子注入層70とし、及び100 nm Al陰極を蒸着する。
まず、透明導電ITOガラス(陽極20の有するガラス基板10)を順に洗浄剤溶液及び脱イオン水、エタノール、アセトン、脱イオン水によって洗浄を行う。さらに酸素プラズマを使用して30s処理し、その後プラズマにより処理されたCFxで処理を行う。
その後、ITOに60nm厚さの2−TNATAを蒸着して正孔注入層30とする。
その後、NPBを蒸着し、10nm厚さの正孔輸送層40を形成する。
その後、正孔輸送層に30nm厚さのMADNを蒸着して発光層50とする。
その後、発光層に30nm厚さのANP 34を蒸着して電子輸送層60とする。
最後に、1nmのLIFを蒸着して電子注入層70とし、及び100 nm Al陰極を蒸着する。
20 mA/cm2の電流密度下の素子のパラメータ結果は表1に示す。
Claims (20)
- 有機エレクトロルミネセンス材料であって、式(I)の構造を有し、
R 1 〜R 3 は独立に、C6〜C40の1つ若しくは複数の置換基R含有のまたは未置換のアリール基、C6〜C40のアリールラジカル基、C3〜C40の1つの置換基R含有のまたは未置換の1つ若しくは複数のヘテロ原子含有のアリール基を表し、前記へテロ原子がO、S、Nで、前記置換基Rがハロゲン、シアン基、ニトロ基、アミノ基、C1〜C4アルキル基、C1〜C4アルコキシ基である、有機エレクトロルミネセンス材料。 - R 2 、R 3 が独立に、C6〜C30の1つまたは複数の置換基R含有のまたは未置換のフェニル基、C10〜C30の1つまたは複数の置換基R含有のまたは未置換の縮合芳香族環、C6〜C20の1つまたは複数の置換基R含有のまたは未置換の1つまたは2つのヘテロ原子含有の五員または六員ヘテロアリール基から選ばれ、前記置換基Rがハロゲン、シアン基、ニトロ基、アミノ基、C1〜C4アルキル基、C1〜C4アルコキシ基で、前記へテロ原子がO、S、Nである、請求項1に記載の有機エレクトロルミネセンス材料。
- R 2 、R 3 が独立に、1つの置換基R含有のまたは未置換のフェニル基、1つの置換基R含有のまたは未置換のナフチル基、1つの置換基R含有のまたは未置換のカルバゾイル基、1つのヘテロ原子含有の五員または六員ヘテロアリール基から選ばれ、前記置換基Rがハロゲン、アミノ基、C1〜C4アルキル基である、請求項1に記載の有機エレクトロルミネセンス材料。
- 前記R 2 、R 3 が同時に、フェニル基、ナフチル基、トリル基、フェノールフタレイン、フラン、ピロールまたはピラジンである、請求項1に記載の有機エレクトロルミネセンス材料。
- R 1 が、C6〜C20の1つの置換基R含有のまたは未置換の1つまたは複数のヘテロ原子含有の五員または六員ヘテロアリール基、C10〜C20の1つの置換基R含有のまたは未置換の縮合芳香族環基、C6〜C30の1つまたは複数の置換基R含有のまたは未置換のフェニル基から選ばれ、前記置換基Rがハロゲン、シアン基、ニトロ基、アミノ基、C1〜C4アルキル基、C1〜C4アルコキシ基で、前記へテロ原子がO、S、Nである、請求項1〜4のいずれか1項に記載の有機エレクトロルミネセンス材料。
- R 1 が、C10〜C20の1つの置換基R含有のまたは未置換のカルバゾイル基、 C10〜C20の1つまたは複数の置換基R含有のまたは未置換のフルオレニル基、ナフチル基、フェニル基、C6〜C10の1つの置換基R含有のまたは未置換の1つまたは複数のヘテロ原子含有の五員または六員ヘテロアリール基から選ばれる、請求項5に記載の有機エレクトロルミネセンス材料。
- 前記1つまたは複数のヘテロ原子含有の五員または六員ヘテロアリール基がピリミジニル基、ピリジン基、チアゾール基、トリアゾールまたはトリアジン基で、前記1つまたは複数の置換基R含有のまたは未置換のフルオレニル基が9,9−ジメチルフルオレニル、9,9−ジフェニルフルオレニル、9,9−キシレンフルオレニルまたはスピロフルオレンである、請求項6に記載の有機エレクトロルミネセンス材料。
- 前記R 2 、R 3 が同時にフェニル基であり、R 1 が1つの置換基Rに置換されたフェニル基、ナフチル基、カルバゾイル基で、またはR 1 が9,9−ジメチルフルオレニル、9,9−ジフェニルフルオレニル、9,9−キシレンフルオレニルまたはスピロフルオレンで、前記置換基Rがハロゲン、C1〜C4アルキル基である、請求項7に記載の有機エレクトロルミネセンス材料。
- 以下の化合物である、
請求項1に記載の有機エレクトロルミネセンス材料。 - 以下の化合物である、
請求項1に記載の有機エレクトロルミネセンス材料。 - 請求項1〜10のいずれか1項に記載の有機エレクトロルミネセンス材料の製作方法であって、
を製作するステップ(1)と、
さらにR 1 −CNと、窒素ガスの保護下で、250〜300℃にて40〜50h反応させて製作するステップ(2)を含む、有機エレクトロルミネセンス材料の製作方法。 - 前記ステップ(2)における反応は、原料を窒素ガスの保護下で混合し、直接加熱して反応させる、請求項11に記載の製作方法。
- 前記ステップ(2)における反応は、溶媒ジフェニルエーテルを加え、40〜50h加熱還流し、原料を窒素ガスの保護下で混合し、直接加熱して反応させる、請求項11に記載の製作方法。
- 前記ステップ(2)の後はさらに再結晶純化ステップを含み、前記再結晶はジクロロメタン−アセトンの混合溶媒を使用して再結晶純化を行い、前記ステップ(2)における反応は、原料を窒素ガスの保護下で混合し、直接加熱して反応させる、請求項11に記載の製作方法。
- 前記再結晶の前はさらにシリカゲルカラム純化ステップを含み、石油エーテルを使用してリンスを行う、請求項14に記載の製作方法。
- 前記ステップ(1)の製作方法は、窒素ガス及び強アルカリ条件下で、アセナフテンキノン及び
を70〜100℃下で還流して製作する、請求項11に記載の製作方法。 - 前記強アルカリ条件は、溶液に水酸化カリウムまたは水酸化ナトリウムを加え、前記還流溶液における溶媒はエタノールである、請求項14に記載の製作方法。
- 請求項1〜10のいずれか1項に記載の有機エレクトロルミネセンス材料の含有する有機エレクトロルミネセンス素子。
- 請求項1〜10のいずれか1項に記載の有機エレクトロルミネセンス材料を電子輸送材料とし、または/及び、発光層における赤色燐光の主体材料とする、請求項18に記載の有機エレクトロルミネセンス素子。
- オブジェクト(客体)材料は有機イリジウム化合物または有機白金化合物である、請求項19に記載の有機エレクトロルミネセンス素子。
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PCT/CN2014/090192 WO2015067155A1 (zh) | 2013-11-11 | 2014-11-03 | 有机电致发光材料和有机电致发光器件 |
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US10727423B2 (en) | 2016-06-20 | 2020-07-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
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