JP2013093617A - 有機エレクトロルミネッセンス素子、表示装置および照明装置 - Google Patents
有機エレクトロルミネッセンス素子、表示装置および照明装置 Download PDFInfo
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Abstract
Description
2.前記燐光性化合物のHOMOが−4.80〜−3.50eV、LUMOが−0.80〜+1.00eVであることを特徴とする前記1に記載の有機エレクトロルミネッセンス素子。
8.前記一般式(I)で表される燐光性化合物において、m2が0であることを特徴とする前記7に記載の有機エレクトロルミネッセンス素子。
14.前記一般式(II)において、R2で表される置換基が下記一般式(III)で表されることを特徴とする前記13に記載の有機エレクトロルミネッセンス素子。
15.前記一般式(3)が、メシチル基(2,4,6−トリメチルフェニル基)、であることを特徴とする前記14に記載の有機エレクトロルミネッセンス素子。
X−CH2COORX+H2O→X−CH2COOH+RXOH
で表される、酢酸のメチル基の水素原子1つを置換基Xで置換したα位モノ置換酢酸から誘導されるα位モノ置換酢酸エステルを酸性条件下で加水分解する際の反応速度定数kXと、次の化学反応式
CH3COORY+H2O→CH3COOH+RYOH
(RXはRYと同じである)で表される、上記のα位モノ置換酢酸エステルに対応する酢酸エステルを酸性条件下で加水分解する際の反応速度定数kHから次の式で求められる。
置換基Xの立体障害により反応速度は低下し、その結果kX<kHとなるのでEs値は通常負となる。実際にEs値を求める場合には、上記の二つの反応速度定数kXとkHを求め、上記の式により算出する。
式中、Xは励起三重項エネルギー(eV)、Yはリン光の0−0バンド(nm)を表す。リン光の0−0バンド(nm)は、下記のようにして求めることができる。
請求の範囲第5項〜第18項の構成に係わる発明の一般式(I)で表される燐光性化合物について説明する。
(i)陽極/発光層/陰極
(ii)陽極/正孔輸送層/発光層/陰極
(iii)陽極/正孔輸送層/発光層/電子輸送層/陰極
(iv)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極バッファー層層/陰極
(v)陽極/正孔輸送層/正孔輸送層A/発光層/電子輸送層/陰極バッファー層/陰極
(vi)陽極/正孔輸送層/正孔輸送層A/発光層/電子輸送層A/電子輸送層/陰極バッファー層/陰極
《発光層》
請求の範囲第5項〜第18項の構成本発明に係る発光層について説明する。
本発明の有機EL素子の発光層には、燐光性化合物(リン光性ドーパント、リン光発光性化合物ともいう)とホスト化合物が含有される。本発明においては、燐光性化合物として前述した本発明に係る化合物を用いることが好ましい。
更に公知の燐光性化合物を複数種併用してもよい。リン光性ドーパントを複数種用いることで、異なる発光を混ぜることが可能となり、これにより任意の発光色を得ることができる。リン光性ドーパントの種類、ドープ量を調整することで白色発光が可能であり、照明、バックライトへの応用もできる。
発光層に使用される材料としては、上記の燐光性ドーパントの他に発光ホスト化合物がある。
本発明の有機EL素子の構成層について説明する。
(ii)陽極/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極
(iii)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
(iv)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
(v)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/陰極バッファー層/陰極
(vi)陽極/陽極バッファー層/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(vii)陽極/陽極バッファー層/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
(viii)陽極/正孔輸送層/中間層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極
この中でも、請求の範囲第1項〜第4項、及び第13項〜第18項の構成に係わる発明においては(viii)の構成が最も好ましい。
本発明に係る中間層とは発光層と正孔輸送層との間の層のことである。該層に含まれる材料の性質によっては、該層を正孔輸送層と呼ぶこともあり、電子阻止層と呼ぶこともある。本発明においては、該中間層中に発光層に含有されるホスト化合物と同じ材料を含有することが好ましい。
本発明に係る阻止層(例えば、電子阻止層、正孔阻止層)について説明する。
正孔阻止層とは広い意味では電子輸送層の機能を有し、電子を輸送する機能を有しつつ正孔を輸送する能力が著しく小さい材料からなり、電子を輸送しつつ正孔を阻止することで電子と正孔の再結合確率を向上させることができる。
一方、電子阻止層とは広い意味では正孔輸送層の機能を有し、正孔を輸送する機能を有しつつ電子を輸送する能力が著しく小さい材料からなり、正孔を輸送しつつ電子を阻止することで電子と正孔の再結合確率を向上させることができる。また、後述する正孔輸送層の構成を必要に応じて電子阻止層として用いることができる。
正孔輸送層とは正孔を輸送する機能を有する材料を含み、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。正孔輸送層は単層もしくは複数層設けることができる。
本発明の請求の範囲第5項〜第18項の構成に係る正孔輸送層Aについて説明する。
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、単層もしくは複数層を設けることができる。
本発明の請求の範囲第5項〜第18項の構成に係る電子輸送層Aについて説明する。
注入層は必要に応じて設け、電子注入層と正孔注入層があり、上記のごとく陽極と発光層または正孔輸送層の間、及び陰極と発光層または電子輸送層との間に存在させてもよい。
本発明の有機EL素子に係る陽極としては、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。このような電極物質の具体例としては、Au等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。また、IDIXO(In2O3−ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、あるいはパターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。更に膜厚は材料にもよるが通常10〜1000nm、好ましくは10〜200nmの範囲で選ばれる。
一方、本発明に係る陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、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用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム−カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させて作製することができる。また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10〜1000nm、好ましくは50〜200nmの範囲で選ばれる。なお発光を透過させるため、有機EL素子の陽極または陰極のいずれか一方が透明または半透明であれば、発光輝度が向上し好都合である。
本発明の有機EL素子に係る基体としては、ガラス、プラスチック等の種類には特に限定はなく、また透明のものであれば特に制限はないが、好ましく用いられる基板としては、例えば、ガラス、石英、光透過性樹脂フィルムを挙げることができる。特に好ましい基体は、有機EL素子にフレキシブル性を与えることが可能な樹脂フィルムである。
本発明の請求の範囲第1項〜第4項、及び第13項〜第18項の構成に係わる有機EL素子の作製方法の一例として、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/陰極バッファー層/陰極からなる有機EL素子の作製法について説明する。
本発明の請求の範囲第1項〜第4項、及び第13項〜第18項の構成に係わる表示装置について説明する。本発明の表示装置は上記有機EL素子を有する。
本発明の請求の範囲第5項〜第18項の構成に係わる有機EL素子の作製方法の一例として、図1に示した、陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極バッファー層/陰極からなる有機EL素子の作製法について説明する。
本発明の請求の範囲第5項〜第18項の構成に係わる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上記有機EL素子を有する。
《材料のHOMO準位及びLUMO準位の計算》
以下に示す化合物について、HOMO、LUMOの値を計算した。米国Gaussian社製の分子軌道計算用ソフトウェアであるGaussian98(Gaussian98、Revision A.11.4,M.J.Frisch,et al.,Gaussian,Inc.,Pittsburgh PA,2002.)を用いて計算した時の値であり、ホスト化合物のHOMO、LUMOの値はキーワードとしてB3LYP/6−31G*を用い、燐光性化合物のHOMO、LUMOの値は、キーワードとしてB3LYP/LanL2DZを用いて算出した。結果を以下に示す。
陽極としてガラス上にITOを150nm成膜した基板(NHテクノグラス社製:NA−45)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iso−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。この透明支持基板を市販の真空蒸着装置の基板ホルダーに固定し、一方、5つのタンタル製抵抗加熱ボートに、α−NPD、CBP、Fir(pic)、BC、Alq3をそれぞれ入れ、真空蒸着装置(第1真空槽)に取付けた。更に、タンタル製抵抗加熱ボートにフッ化リチウムを、タングステン製抵抗加熱ボートにアルミニウムをそれぞれ入れ、真空蒸着装置の第2真空槽に取り付けた。
有機EL素子1−1の作製において、表2に記載のようにホスト化合物、燐光性化合物を変更した以外は同様にして、有機EL素子1−2〜1−19を作製した。
得られた有機EL素子1−1〜1−19について室温下、1000cd/m2の輝度を与える電圧を測定した。駆動電圧は、有機EL素子1−1を100とする相対値で表した。得られた結果を表3に示す。
陽極としてガラス上にITOを150nm成膜した基板(NHテクノグラス社製:NA−45)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iso−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た。この透明支持基板上に、ポリ(3,4−エチレンジオキシチオフェン)−ポリスチレンスルホネート(PEDOT/PSS、Bayer社製、Baytron P Al 4083)を純水で70%に希釈した溶液を3000rpm、30秒でスピンコート法により製膜した後、200℃にて1時間乾燥し、膜厚30nmの正孔注入層を設け、その後、市販の真空蒸着装置の基板ホルダーに固定した。
有機EL素子1−20の作製において、表4に記載のようにホスト化合物、燐光性化合物の材料を変更した以外は同様にして、有機EL素子1−21〜1−27を作製した。
得られた有機EL素子1−20〜1−27について室温下、1500cd/m2の輝度を与える電圧を測定した。駆動電圧は、有機EL素子1−20を100とする相対値で表した。得られた結果を表4に示す。
《フルカラー表示装置の作製》
(青色発光素子の作製)
実施例1の有機EL素子1−10を青色発光素子として用いた。
実施例1の有機EL素子1−10において、ホスト化合物をCBP、ドーパントをIr(ppy)3に変更した以外は同様にして緑色発光素子を作製し、これを緑色発光素子として用いた。
実施例1の有機EL素子1−10において、ホスト化合物をCBP、ドーパントをIr(btpy)3に変更した以外は同様にして赤色発光素子を作製し、これを赤色発光素子として用いた。
《白色発光素子及び白色照明装置の作製》
実施例1の透明電極基板の電極を20mm×20mmにパターニングし、その上に実施例1と同様に正孔注入/輸送層としてα−NPDを90nmの厚さで成膜し、更にH−25の入った前記加熱ボートと化合物1−2の入ったボート及びIr(btpy)3の入ったボートをそれぞれ独立に通電して、ホスト化合物であるH−25、燐光性化合物である1−2、及びIr(btpy)3の蒸着速度が100:5:0.6になるように調節し、膜厚30nmの厚さになるように蒸着し、発光層を設けた。
〈有機EL素子1a−1〜1a−11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150nm製膜した基板(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分間行なった。この透明支持基板を市販の真空蒸着装置の基板ホルダーに固定し、一方モリブデン製抵抗加熱ボートにα−NPDを200mg入れ、別のモリブデン製抵抗加熱ボートに例示化合物HA−9を200mg入れ、別のモリブデン製抵抗加熱ボートに例示リン光性化合物1−1を100mg入れ、更に別のモリブデン製抵抗加熱ボートにBAlqを200mg入れ、真空蒸着装置に取付けた。
有機素子1a−1において、ホスト化合物およびリン光性化合物を表5のように変えた以外は、有機EL素子1a−1と同様にして有機EL素子1a−12〜1a−14を作製した。
作製した有機EL素子について、23℃、乾燥窒素ガス雰囲気下で2.5mA/cm2定電流を印加した時の外部取り出し量子効率(%)を測定した。尚、測定には分光放射輝度計CS−1000(コニカミノルタセンシング製)を用いた。
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150nm製膜した基板(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た。
有機素子1a−15において、ホスト化合物およびリン光性化合物を表6のように変えた以外は、有機EL素子1a−1と同様にして有機EL素子1a−22〜1a−23を作製した。
作製した有機EL素子について、23℃、乾燥窒素ガス雰囲気下で輝度500cd/m2の輝時の外部取り出し量子効率(%)を測定した。尚、測定には分光放射輝度計CS−1000(コニカミノルタセンシング製)を用いた。
〈有機EL素子2−1〜2−10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製膜した基板(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分間行なった。この透明支持基板を市販の真空蒸着装置の基板ホルダーに固定し、一方モリブデン製抵抗加熱ボートにα−NPDを200mg入れ、別のモリブデン製抵抗加熱ボートに例示正孔輸送性化合物HT−36を200mg入れ、別のモリブデン製抵抗加熱ボートに例示化合物HA−9を200mg入れ、別のモリブデン製抵抗加熱ボートに例示化合物1−1を100mg入れ、更に別のモリブデン製抵抗加熱ボートにBAlqを200mg入れ、真空蒸着装置に取付けた。
有機素子2−1において、正孔輸送層Aの材料、ホスト化合物、リン光性化合物および電子輸送層A化合物を表7のように変えた以外は、有機EL素子2−1と同様にして有機EL素子2−14〜2−15を作製した。
作製した有機EL素子について、23℃、乾燥窒素ガス雰囲気下で2.5mA/cm2定電流を印加した時の外部取り出し量子効率(%)を測定した。尚、測定には分光放射輝度計CS−1000(コニカミノルタセンシング製)を用いた。
《有機EL素子3−1〜3−10の作製》
有機EL素子1a−1〜1a−11において、NPDをm−MTDATA:F4−TCNQ(質量比99:1)共蒸着膜10nmとNPD膜10nmの積層に変更し、BAlqをBAlq膜10nmとBPhen:Cs(質量比75:25)共蒸着膜20nmの積層に変更し、LiFを蒸着しなかった以外は同様にして有機EL素子3−1〜3−11を作製した。
実施例4で作製した有機EL素子1a−1において、例示リン光性化合物1−1に代えて例示リン光性化合物1−1、Ir−1、Ir−2(1−1:Ir−1:Ir−2=2:1:2)を用いた以外は、有機EL素子1a−1と同様にして有機EL素子4−1を作製した。
有機EL素子4−1の非発光面をガラスケースで覆い、発光面にカラーフィルターを付け画像表示装置として用いたところ、良好なフルカラーの色表示性能を示し、優れた画像表示装置として使用することができた。
実施例1で作製した有機EL素子1−1において、例示リン光性化合物1−1に代えて例示リン光性化合物1−1、Ir−3(1−1:Ir−3=1:3)を用いた以外は、有機EL素子1a−1と同様にして有機EL素子5−1を作製した。
有機EL素子5−1の非発光面をガラスケースで覆い、照明装置とした。照明装置は、発光効率が高い白色光を発する薄型の照明装置として使用することができた。
3 画素
5 走査線
6 データ線
7 電源ライン
10 有機EL素子
11 スイッチングトランジスタ
12 駆動トランジスタ
13 コンデンサ
A 表示部
B 制御部
107 透明電極付きガラス基板
106 有機EL層
105 陰極
102 ガラスカバー
108 窒素ガス
109 捕水剤
Claims (7)
- 基板上に電極と少なくとも1層の有機層を有し、該有機層の少なくとも1層がホスト化合物と燐光性化合物とを含有する発光層である有機エレクトロルミネッセンス素子において、該ホスト化合物のHOMOが−7.20eV〜−5.42eV、LUMOが−2.30〜−0.50eVであり、該燐光性化合物が一般式(1)で表され、かつ、該ホスト化合物がフラン誘導体であ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。
- 前記燐光性化合物のHOMOが−4.80〜−3.50eV、LUMOが−0.80〜+1.00eVであることを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子。
- 前記一般式(1)で表される燐光性化合物において、m2が0であることを特徴とする請求項1または2に記載の有機エレクトロルミネッセンス素子。
- 前記一般式(1)で表される燐光性化合物において、B1〜B4で形成される含窒素複素環がイミダゾール環であることを特徴とする請求項1〜3のいずれか1項に記載の有機エレクトロルミネッセンス素子。
- 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ッセンス素子を有することを特徴とする表示装置。
- 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ッセンス素子を有することを特徴とする照明装置。
- 請求項6に記載の照明装置と表示手段としての液晶素子を有することを特徴とする表示装置。
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2013
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JP5672648B2 (ja) | 2015-02-18 |
EP1998387A1 (en) | 2008-12-03 |
JPWO2007108362A1 (ja) | 2009-08-06 |
US20090091253A1 (en) | 2009-04-09 |
JP2013138220A (ja) | 2013-07-11 |
EP1998387B1 (en) | 2015-04-22 |
JP5594384B2 (ja) | 2014-09-24 |
EP1998387A4 (en) | 2011-06-15 |
WO2007108362A1 (ja) | 2007-09-27 |
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