JP2013245179A - 金属錯体、有機エレクトロルミネッセンス素子、表示装置及び照明装置 - Google Patents
金属錯体、有機エレクトロルミネッセンス素子、表示装置及び照明装置 Download PDFInfo
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- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
2.前記一般式(1)で表される配位子を有する金属錯体が、下記一般式(2)で表されることを特徴とする前記第1項に記載の金属錯体。
3.前記一般式(1)又は一般式(2)において、ngが1を表し、連結基Gが−O−、−S−、−C(R1)2−、−C(=O)−又は−C(=O)O−のいずれかである、ただしR1は水素原子又は置換基を表し、2つのR1は同じでも異なっていても良い、ことを特徴とする前記第1項又は第2項に記載の金属錯体。
本発明の有機EL素子の構成層について説明する。
(ii)陽極/正孔輸送層/発光層/電子輸送層/陰極
(iii)陽極/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極
(iv)陽極/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(v)陽極/陽極バッファー層/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(vi)陽極//正孔輸送層/陽極バッファー層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(vii)陽極/陽極バッファー層/正孔輸送層/発光層/電子輸送層/陰極バッファー層/陰極
発光層は、ユニットを形成して発光層ユニットとしてもよい。更に、発光層間には非発光性の中間層を有していてもよく、中間層は電荷発生層を含んでいてもよい。
電子輸送層とは電子を輸送する機能を有する材料からなり、広い意味で電子注入層、正孔阻止層も電子輸送層に含まれる。電子輸送層は単層若しくは複数層を設けることができる。
本発明に係る発光層は、電極又は電子輸送層、正孔輸送層から注入されてくる電子及び正孔が再結合して発光する層であり、発光する部分は発光層の層内であっても発光層と隣接層との界面であってもよい。
発光性ドーパント化合物(発光ドーパントともいう。)について説明する。
本発明に係るリン光ドーパント(リン光発光ドーパントともいう。)について説明する。
上記中間体N1から配位子1の合成及び配位子1から金属錯体(例示化合物(13))の合成は、米国特許公報第2011/020433号明細書を参考に合成した。参考までに反応スキームを下記に示す。
蛍光ドーパント(蛍光性化合物ともいう)としては、クマリン系色素、ピラン系色素、シアニン系色素、クロコニウム系色素、スクアリウム系色素、オキソベンツアントラセン系色素、フルオレセイン系色素、ローダミン系色素、ピリリウム系色素、ペリレン系色素、スチルベン系色素、ポリチオフェン系色素、又は希土類錯体系蛍光体等や、レーザー色素に代表される蛍光量子収率が高い化合物が挙げられる。
また、発光ドーパントは、複数種の化合物を併用して用いてもよく、構造の異なるリン光ドーパント同士の組み合わせや、リン光ドーパントと蛍光ドーパントを組み合わせて用いてもよい。
本発明の有機EL素子の発光層に含まれるホスト化合物とは、室温(25℃)におけるリン光発光のリン光量子収率が、0.1未満の化合物であることが好ましく、更に好ましくはリン光量子収率が0.01未満の化合物である。
Qm−Ln
一般式(H1)において、Qで表される置換していても良い芳香族炭化水素環又は芳香族複素環としては、前述の一般式(1)の環Vにおける芳香族炭化水素環及び芳香族複素環と同様のものが挙げられる。
正孔輸送層とは正孔を輸送する機能を有する正孔輸送材料からなり、広い意味で正孔注入層、電子阻止層も正孔輸送層に含まれる。正孔輸送層は単層又は複数層設けることができる。
阻止層は、前記有機化合物薄膜の基本的な構成層の他に、必要に応じて設けられるものである。例えば、特開平11−204258号公報、同11−204359号公報、及び「有機EL素子とその工業化最前線(1998年11月30日エヌ・ティー・エス社発行)」の237頁等に記載されている正孔阻止(ホールブロック)層がある。
注入層には、正孔注入層と電子注入層がある。
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。
一方、陰極としては仕事関数の小さい(4eV以下)金属(電子注入性金属)、合金、電気伝導性化合物及びこれらの混合物を電極物質として用いられる。
本発明の有機EL素子に用いることのできる支持基板(以下、基体、基板、基材、支持体等ともいう)としては、ガラス、プラスチック等、種類には特に限定はなく、また透明であっても不透明であってもよい。支持基板側から光を取り出す場合には、支持基板は透明であることが好ましい。
い。
有機EL素子の製造方法の一例として、陽極/正孔注入層/正孔輸送層/発光層/正孔阻止層/電子輸送層/電子注入層/陰極から構成される有機EL素子の製造方法について説明する。
本発明の有機EL素子は、陽極、陰極、及び陽極と陰極との間に設けられる各層を、封止部材によって外気から遮断して封止しておくことが好ましい。
有機層を挟み支持基板と対向する側の封止膜又は封止用フィルムの外側に、有機EL素子の機械的強度を高めるため、保護膜又は保護板を設けてもよい。特に封止が封止膜により行われている場合には、その機械的強度は必ずしも高くないため、このような保護膜又は保護板を設けることが好ましい。
有機EL素子は空気よりも屈折率の高い(屈折率が1.7〜2.1程度)層の内部で発光し、発光層で発生した光のうち15〜20%程度の光しか取り出せないと一般的に言われている。これは、臨界角以上の角度θで界面(透明基板と空気との界面)に入射する光は全反射を起こし、有機EL素子の外部に取り出すことができないことや、透明電極ないし発光層と透明基板との間で光が全反射を起こし、光が透明電極ないし発光層を導波し、結果として光が有機EL素子の側面方向に逃げるためである。
本発明の有機EL素子は、基板の光取り出し側に、例えば、マイクロレンズアレイ状の構造を設けるように加工すること、又は集光シートと組み合わせることにより、特定方向、例えば、有機EL素子発光面に対し正面方向に集光することにより、特定方向上の輝度を高めることができる。
本発明の有機EL素子は、表示デバイス、ディスプレイ、各種発光光源として用いることができる。
本発明の表示装置について説明する。本発明の表示装置は、本発明の有機EL素子を具備したものである。本発明の表示装置は単色でも多色でもよいが、ここでは多色表示装置について説明する。
本発明の照明装置について説明する。本発明の照明装置は、本発明の有機EL素子を有する。
本発明の有機EL素子を具備した、本発明の照明装置の一態様について説明する。
比較化合物1を例にして、本発明に係る環Vと連結基Gのファンデルワールス体積の合計値の求め方を以下に示す。
1)比較化合物1で表される金属錯体の最安定化構造を、米国Gaussian社製の分子軌道計算用ソフトウェアであるGaussian03を用いて分子計算により求める。
2)該最安定化構造において、環Aと連結基G又は環Vの結合を切断し、環Aを含む部分構造を削除する。具体的には上記、右図において点線で表される部分が環Aを含む部分構造に該当する。
3)残った連結基G及び環Vのファンデルワールス体積を求める。具体的には上記右図の点線枠で囲った部分、より具体的にはビフェニルから水素原子を1つ除いた構造、のファンデルワールス体積を求める。
≪。有機EL素子1−1の作製≫
陽極として100mm×100mm×1.1mmのガラス基板上にITO(インジウムチンオキシド)を100nm成膜した基板(NHテクノグラス社製NA45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をイソプロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。
有機EL素子1−1の作製において、ドーパント化合物である比較化合物1を表1に記載のドーパント化合物に変えた以外は同様にして有機EL素子1−2〜1−20を作製した。
有機EL素子1−1の作製において、発光層形成時に使用するホスト化合物HS−3を100mg、ドーパント化合物の比較化合物1を50mgに変更し、ドーパント化合物とホスト化合物の比率を変えてドーパント化合物の比率を12質量%から33質量%に増やした以外は有機EL素子1−1の作製同様にして、有機EL素子2−1を作製した。
有機EL素子2−1の作製において、ドーパント化合物である比較化合物1を表1に記載の化合物に変えた以外は有機EL素子2−1の作製と同様にして有機EL素子2−2〜2−20を作製した。それぞれドーパント化合物の比率のみ変えた組み合わせをサンプル2〜20とし、表1に示した。
得られた有機EL素子を評価するに際しては、作製後の各有機EL素子の非発光面をガラスカバーで覆い、ガラスカバーと有機EL素子が作製されたガラス基板とが接触するガラスカバー側の周囲にシール剤としてエポキシ系光硬化型接着剤(東亞合成社製ラクストラックLC0629B)を適用し、これを上記陰極側に重ねて前記透明支持基板と密着させ、ガラス基板側から有機EL素子を除いた部分にUV光を照射して硬化させ、封止して、下記の図3,4に示すような照明装置を形成して評価した。
有機EL素子1−1〜1−20及び有機EL素子2−1〜2−20を室温(約23℃〜25℃)、2.5mA/cm2の定電流条件下で発光させ、発光開始直後の発光輝度(L)[cd/m2]を測定することにより、外部取り出し量子効率(η)を算出した。
この値が100に近い値を示すほど、ドーパント化合物の量を増やしても発光効率が低下しないことを示す。
有機EL素子1−1〜1−20及び有機EL素子2−1〜2−20を室温下、初期輝度1000cd/m2を示す定電流条件下による連続発光を行い、初期輝度の70%の輝度になるのに要する時間(τ70)を測定し発光寿命とした。さらに表1に表されるサンプル番号Xによって有機EL素子1−Xと有機EL素子2−Xの各寿命の変化率を求め、下記、表2には各サンプルに対し、サンプル番号4の変化率を1.00とする相対値として、寿命変化を表した。なお、変化率は、サンプル番号4、有機EL素子1−4と有機EL素子2−4の場合であれば下記、式(A)で求められ、各サンプル番号Xの寿命変化は下記、式(B)で求められる。
(変化率)=(有機EL素子2−4の発光寿命/有機EL素子1−4の発光寿命)×100
式(B)
(寿命変化)=(各サンプル番号の変化率/サンプル番号4の変化率)×100
表2には環Vと連結基Gのファンデルワールス体積の合計値を共に示した。
≪有機EL素子3−1の作製≫
陽極として100mm×100mm×1.1mmのガラス基板上にITO(インジウム錫酸化物)を100nm成膜した基板(NHテクノグラス社製)にパターニングを行った後、このITO透明電極を設けた透明支持基板をイソプロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。
有機EL素子3−1の作製において、ドーパント化合物の比較化合物2を表3に記載のドーパント化合物に変えた以外は同様にして有機EL素子3−2〜3−11を作製した。
得られた有機EL素子を評価するに際しては、作製後の各有機EL素子の非発光面をガラスカバーで覆い、ガラスカバーと有機EL素子が作製されたガラス基板とが接触するガラスカバー側の周囲にシール剤としてエポキシ系光硬化型接着剤(東亞合成社製ラクストラックLC0629B)を適用し、これを上記陰極側に重ねて前記透明支持基板と密着させ、ガラス基板側から有機EL素子を除いた部分にUV光を照射して硬化させ、封止して、下記の図3,4に示すような照明装置を形成して評価した。
有機EL素子3−1〜3−11を室温下、輝度300cd/m2を示す電流条件で発光させたときの、電圧を測定し、駆動電圧とした。なお、駆動電圧は有機EL素子3−1を100とした相対値で示した。駆動電圧の数字が小さい程、低電圧から発光することを示す。
有機EL素子3−1〜3−11を室温下、初期輝度1000cd/m2を示す定電流条件下による連続発光を行い、初期輝度の70%の輝度になるのに要する時間(τ70)を測定した。なお、発光寿命は有機EL素子3−2を100と設定する相対値で表3に表した。また、表3には、環Vと連結基Gのファンデルワールス体積の合計値を示した。
《有機EL素子4−1の作製》
100mm×100mm×1.1mmのガラス基板上に、陽極としてITO(インジウムチンオキシド)を100nm成膜した基板(AvanStrate株式会社製、NA−45)にパターニングを行った。その後、このITO透明電極を設けた透明支持基板をイソプロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥して、UVオゾン洗浄を5分間行った。
有機EL素子4−1の作製において、発光層における比較化合物1を表4に示すドーパント化合物に変更した以外は同様にして、有機EL素子4−2〜4−15を各々作製した。
得られた有機EL素子を評価するに際しては、作製後の各有機EL素子の非発光面をガラスカバーで覆い、ガラスカバーと有機EL素子が作製されたガラス基板とが接触するガラスカバー側の周囲にシール剤としてエポキシ系光硬化型接着剤を適用し、これを上記陰極側に重ねて前記透明支持基板と密着させ、ガラス基板側から有機EL素子を除いた部分にUV光を照射して硬化させ、封止して、下記の図3,4に示すような照明装置を形成して評価した。
有機EL素子4−1〜4−15を室温(約23℃〜25℃)、2.5mA/cm2の定電流条件下で発光させ、発光開始直後の発光輝度(L)[cd/m2]を測定することにより、外部取り出し量子効率(η)を算出した。
有機EL素子4−1〜4−15を室温下、初期輝度1000cd/m2を示す定電流条件下による連続発光を行い、初期輝度の70%の輝度になるのに要する時間(τ70)を測定した。なお、発光寿命は有機EL素子4−4を100と設定する相対値で表3に示した。また、表3には、環Vと連結基Gのファンデルワールス体積の合計値を示した。
≪有機EL素子5−1の作製≫
陽極として100mm×100mm×1.1mmのガラス基板上にITO(インジウム錫酸化物)を100nm成膜した基板(NHテクノグラス社製NA45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をイソプロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。
前記有機EL素子5−1の作製において、本発明の金属錯体(13)を比較化合物2に替えた以外は同様にして有機EL素子5−2を作製した。
3 画素
5 走査線
6 データ線
A 表示部
B 制御部
101 有機EL素子
102 ガラスカバー
105 陰極
106 有機EL層
107 透明電極付きガラス基板
108 窒素ガス
109 捕水剤
Claims (10)
- 下記一般式(1)で表される配位子を有する金属錯体であって、連結基Gと環Vとのそれぞれのファンデルワールス体積の合計値が、155Å3以上であることを特徴とする金属錯体。
- 前記一般式(1)又は一般式(2)において、ngが1を表し、連結基Gが−O−、−S−、−C(R1)2−、−C(=O)−又は−C(=O)O−のいずれかである、ただしR1は水素原子又は置換基を表し、2つのR1は同じでも異なっていても良い、ことを特徴とする請求項1又は請求項2に記載の金属錯体。
- 前記一般式(1)又は一般式(2)において、ngが1であり、連結基Gが単環の芳香族炭化水素環又は芳香族複素環を表し、さらに連結基G及び環Aが、硫黄原子、酸素原子、炭素原子又は窒素原子を介して縮合環を形成し、当該縮合環がカルバゾール環、ジベンゾフラン環、ジベンゾチオフェン環、フルオレン環又はフルオレノン環のいずれかであることを特徴とする請求項1又は請求項2に記載の金属錯体。
- 前記一般式(1)又は一般式(2)中、環Aの、前記イミダゾール環と結合している原子と隣接している2つの原子が、共に置換基を有し、少なくとも一方の置換基は炭素原子数3以上の分岐アルキル基であることを特徴とする請求項1から請求項4までのいずれか一項に記載の金属錯体。
- 陽極と陰極との間に、有機層を有する有機エレクトロルミネッセンス素子であって、前記有機層が、請求項1から請求項5までのいずれか一項に記載の金属錯体を含有することを特徴とする有機エレクトロルミネッセンス素子。
- 前記金属錯体を有する有機層が、湿式法により形成された有機層であることを特徴とする請求項6に記載の有機エレクトロルミネッセンス素子。
- 白色発光することを特徴とする請求項6又は請求項7に記載の有機エレクトロルミネッセンス素子。
- 請求項6から請求項8までのいずれか一項に記載の有機エレクトロルミネッセンス素子が具備されていることを特徴とする表示装置。
- 請求項6から請求項8までのいずれか一項に記載の有機エレクトロルミネッセンス素子が具備されていることを特徴とする照明装置。
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