JP4876333B2 - Light emitting element - Google Patents
Light emitting element Download PDFInfo
- Publication number
- JP4876333B2 JP4876333B2 JP2001167809A JP2001167809A JP4876333B2 JP 4876333 B2 JP4876333 B2 JP 4876333B2 JP 2001167809 A JP2001167809 A JP 2001167809A JP 2001167809 A JP2001167809 A JP 2001167809A JP 4876333 B2 JP4876333 B2 JP 4876333B2
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- JP
- Japan
- Prior art keywords
- group
- derivatives
- light emitting
- light
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000000463 material Substances 0.000 claims description 93
- 239000000126 substance Substances 0.000 claims description 14
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- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000011159 matrix material Substances 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
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- 125000004185 ester group Chemical group 0.000 description 3
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Electroluminescent Light Sources (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、電気エネルギーを光に変換できる素子であって、表示素子、フラットパネルディスプレイ、バックライト、照明、インテリア、標識、看板、電子写真機、光信号発生器などの分野に利用可能な発光素子に関する。
【０００２】
【従来の技術】
陰極から注入された電子と陽極から注入された正孔が両極に挟まれた有機蛍光体内で再結合する際に発光するという有機積層薄膜発光素子の研究が近年活発に行われている。この素子は、薄型、低駆動電圧下での高輝度発光、蛍光材料を選ぶことによる多色発光が特徴であり注目を集めている。
【０００３】
この研究は、コダック社のＣ．Ｗ．Ｔａｎｇらが有機積層薄膜素子が高輝度に発光することを示して以来（Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５１（１２）２１，ｐ．９１３，１９８７）、多くの研究機関が検討を行っている。コダック社の研究グループが提示した有機積層薄膜発光素子の代表的な構成は、ＩＴＯガラス基板上に正孔輸送性のジアミン化合物、発光層である８−ヒドロキシキノリンアルミニウム、そして陰極としてＭｇ：Ａｇを順次設けたものであり、１０Ｖ程度の駆動電圧で１０００ｃｄ／ｍ2の緑色発光が可能であった。現在の有機積層薄膜発光素子は、上記の素子構成要素の他に電子輸送層を設けているものなど構成を変えているものもあるが、基本的にはコダック社の構成を踏襲している。
【０００４】
発光層はホスト材料のみで構成されたり、ホスト材料にゲスト材料をドーピングして構成される。発光材料は三原色揃うことが求められているが、これまでは緑色発光材料の研究が最も進んでいる。現在は赤色発光材料と青色発光材料において、特性向上を目指して鋭意研究がなされている。特に青色発光材料において高輝度で色純度の良い発光の得られるものが望まれている。
【０００５】
ホスト材料としては、前述のトリス（８−キノリノラト）アルミニウムを始めとするキノリノール誘導体の金属錯体、ベンズオキサゾール誘導体、スチルベン誘導体、ベンズチアゾール誘導体、チアジアゾール誘導体、チオフェン誘導体、テトラフェニルブタジエン誘導体、シクロペンタジエン誘導体、オキサジアゾール誘導体、オキサジアゾール誘導体金属錯体、ベンズアゾール誘導体金属錯体などがあげられる。
【０００６】
青色発光ホスト材料においては、比較的良い性能が得られている例として、キノリノール誘導体と異なる配位子を組み合わせた金属錯体（特開平５−２１４３３２号公報）や、ビススチリルベンゼン誘導体（特開平４−１１７４８５号公報）などがあげられるが、特に色純度が充分ではない。
【０００７】
一方、ゲスト材料としてのドーパント材料には、レーザー色素として有用であることが知られている、７−ジメチルアミノ−４−メチルクマリンを始めとするクマリン誘導体、ペリレン、ピレン、アントラセンなどの縮合芳香環誘導体、スチルベン誘導体、オリゴフェニレン誘導体、フラン誘導体、キノロン誘導体、オキサゾール誘導体、オキサジアゾール誘導体などが知られている。
【０００８】
【発明が解決しようとする課題】
しかし、従来技術に用いられる発光材料（ホスト材料、ドーパント材料）には、発光効率が低く消費電力が高いものや、耐久性が低く素子寿命の短いものが多かった。また、フルカラーディスプレイとして赤色、緑色、青色の三原色発光が求められているが、赤色、青色発光においては、発光波長を満足させるものは少なく、発光ピークの幅も広く色純度が良いものは少ない。中でも青色発光において、耐久性に優れ十分な輝度と色純度特性を示すものが必要とされている。
【０００９】
また従来、数少ない既存材料を用いても、発光材料と相互作用を起こす、もしくは電子輸送材料自体の発光が混在する等の理由で所望の発光色が得られなかったり、高効率発光が得られるものの耐久性が短い等の問題があった。例えば、特開平５−３３１４５９号公報には特定のフェナントロリン誘導体を電子輸送材料に用いているが、高効率発光を示すものの、長時間の通電により結晶化し、耐久性が著しく短い問題があった。また、発光効率および耐久性に比較的良い特性を示すものとして、キノリノール金属錯体やベンゾキノリノール金属錯体があるが、これらはこの材料自身に高い青緑〜黄色での発光能力があるために、電子輸送材料として用いた際に、これらの材料自身の発光が混在して色純度が悪化する恐れがある。
【００１０】
本発明は、かかる従来技術の問題を解決し、発光効率が高く、高輝度で色純度に優れた発光素子を提供することを目的とするものである。
【００１１】
【課題を解決するための手段】
本発明は、陽極と陰極の間に発光物質が存在し、電気エネルギーにより発光する素子であって、該素子がリンオキサイド基で置換された蛍光性骨格を有する有機蛍光体を含むことを特徴とする発光素子である。
【００１２】
【発明の実施の形態】
本発明において陽極は、光を取り出すために透明であれば酸化錫、酸化インジウム、酸化錫インジウム（ＩＴＯ）などの導電性金属酸化物、あるいは金、銀、クロムなどの金属、ヨウ化銅、硫化銅などの無機導電性物質、ポリチオフェン、ポリピロール、ポリアニリンなどの導電性ポリマなど特に限定されるものでないが、ＩＴＯガラスやネサガラスを用いることが特に望ましい。透明電極の抵抗は素子の発光に十分な電流が供給できればよいので限定されないが、素子の消費電力の観点からは低抵抗であることが望ましい。例えば３００Ω／□以下のＩＴＯ基板であれば素子電極として機能するが、現在では１０Ω／□程度の基板の供給も可能になっていることから、低抵抗品を使用することが特に望ましい。ＩＴＯの厚みは抵抗値に合わせて任意に選ぶ事ができるが、通常１００〜３００ｎｍの間で用いられることが多い。また、ガラス基板はソーダライムガラス、無アルカリガラスなどが用いられ、また厚みも機械的強度を保つのに十分な厚みがあればよいので、０．５ｍｍ以上あれば十分である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、ＳｉＯ2 などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用できる。ＩＴＯ膜形成方法は、電子線ビーム法、スパッタリング法、化学反応法など特に制限を受けるものではない。
【００１３】
本発明において陰極は、電子を本有機物層に効率良く注入できる物質であれ特に限定されないが、一般に白金、金、銀、銅、鉄、錫、亜鉛、アルミニウム、インジウム、クロム、リチウム、ナトリウム、カリウム、カルシウム、マグネシウムなどがあげられるが、電子注入効率をあげて素子特性を向上させるためにはリチウム、ナトリウム、カリウム、カルシウム、マグネシウムまたはこれら低仕事関数金属を含む合金が有効である。しかし、これらの低仕事関数金属は、一般に大気中で不安定であることが多く、例えば、有機層に微量のリチウムやセシウム、マグネシウム（真空蒸着の膜厚計表示で１ｎｍ以下）をドーピングして安定性の高い電極を使用する方法が好ましい例として挙げることができるが、フッ化リチウムのような無機塩の使用も可能であることから特にこれらに限定されるものではない。更に電極保護のために白金、金、銀、銅、鉄、錫、アルミニウム、インジウムなどの金属、またはこれら金属を用いた合金、そしてシリカ、チタニア、窒化ケイ素などの無機物、ポリビニルアルコール、塩化ビニル、炭化水素系高分子などを積層することが好ましい例として挙げられる。これらの電極の作製法も抵抗加熱、電子線ビーム、スパッタリング、イオンプレーティング、コーティングなど導通を取ることができれば特に制限されない。
【００１４】
本発明において発光物質とは、１）正孔輸送層／発光層、２）正孔輸送層／発光層／電子輸送層、３）発光層／電子輸送層、そして、４）以上の組合わせ物質を一層に混合した形態のいずれであってもよい。即ち、素子構成としては、上記１）〜３）の多層積層構造の他に４）のように発光材料単独または発光材料と正孔輸送材料や電子輸送材料を含む層を一層設けるだけでもよい。さらに、本発明における発光物質は自ら発光するもの、その発光を助けるもののいずれにも該当し、発光に関与している化合物、層などを指すものである。
【００１５】
本発明において正孔輸送層は正孔輸送性物質単独または二種類以上の物質を積層、混合するか正孔輸送性物質と高分子結着剤の混合物により形成される。正孔輸送性物質としては電界を与えられた電極間において陽極からの正孔を効率良く輸送することが必要で、正孔注入効率が高く、注入された正孔を効率良く輸送することが望ましい。そのためにはイオン化ポテンシャルが小さく、しかも正孔移動度が大きく、さらに安定性に優れ、トラップとなる不純物が製造時および使用時に発生しにくい物質であることが要求される。このような条件を満たす物質として、特に限定されるものではないが、Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−４，４’−ジフェニル−１，１’−ジアミン、Ｎ，Ｎ’−ジナフチル−Ｎ，Ｎ’−ジフェニル−４，４’−ジフェニル−１，１’−ジアミンなどのトリフェニルアミン類、ビス（Ｎ−アリルカルバゾール）またはビス（Ｎ−アルキルカルバゾール）類、ピラゾリン誘導体、スチルベン系化合物、ヒドラゾン系化合物、オキサジアゾール誘導体やフタロシアニン誘導体、ポルフィリン誘導体に代表される複素環化合物、ポリマー系では前記単量体を側鎖に有するポリカーボネートやスチレン誘導体、ポリビニルカルバゾール、ポリシランなどが好ましいが、素子作製に必要な薄膜を形成し、陽極から正孔が注入できて、さらに正孔を輸送できる化合物であれば特に限定されるものではない。
【００１６】
本発明における発光材料はホスト材料のみでも、ホスト材料とドーパント材料の組み合わせでも、いずれであってもよい。また、ドーパント材料はホスト材料の全体に含まれていても、部分的に含まれていても、いずれであってもよい。ドーパント材料は積層されていても、分散されていても、いずれであってもよい。
【００１７】
本発明において発光材料は、リンオキサイド基で置換された蛍光性骨格を有する有機蛍光体を含む。また、本発明におけるリンオキサイド基で置換された蛍光性骨格を有する有機蛍光体としては、具体的には下記一般式（１）または（２）で表される化合物があげられる。
【００１８】
【化３】
ここでＲ1〜Ｒ3はそれぞれ、水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基の中から選ばれる。また、Ｒ1〜Ｒ3の少なくとも１つは蛍光性骨格である。
【００２０】
【化４】
ここでＲ4〜Ｒ5はそれぞれ、水素、アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、水酸基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン、ハロアルカン、ハロアルケン、ハロアルキン、シアノ基、アルデヒド基、カルボニル基、カルボキシル基、エステル基、カルバモイル基、アミノ基、ニトロ基、シリル基、シロキサニル基の中から選ばれる。Ｘは蛍光性骨格を表す。ｎは２以上の自然数を表す。
【００２２】
これらの置換基の内、アルキル基とは例えばメチル基、エチル基、プロピル基、ブチル基などの飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、シクロアルキル基とは例えばシクロプロピル、シクロヘキシル、ノルボルニル、アダマンチルなどの飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アラルキル基とは例えばベンジル基、フェニルエチル基などの脂肪族炭化水素を介した芳香族炭化水素基を示し、脂肪族炭化水素と芳香族炭化水素はいずれも無置換でも置換されていてもかまわない。また、アルケニル基とは例えばビニル基、アリル基、ブタジエニル基などの二重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、シクロアルケニル基とは例えばシクロペンテニル基、シクロペンタジエニル基、シクロヘキセン基などの二重結合を含む不飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アルキニル基とは例えばアセチレニル基などの三重結合を含む不飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、アルコキシ基とは例えばメトキシ基などのエーテル結合を介した脂肪族炭化水素基を示し、脂肪族炭化水素基は無置換でも置換されていてもかまわない。また、アルキルチオ基とはアルコキシ基のエーテル結合の酸素原子が硫黄原子に置換されたものである。また、アリールエーテル基とは例えばフェノキシ基などのエーテル結合を介した芳香族炭化水素基を示し、芳香族炭化水素基は無置換でも置換されていてもかまわない。また、アリールチオエーテル基とはアリールエーテル基のエーテル結合の酸素原子が硫黄原子に置換されたものである。また、アリール基とは例えばフェニル基、ナフチル基、ビフェニル基、フェナントリル基、ターフェニル基、ピレニル基などの芳香族炭化水素基を示し、これは無置換でも置換されていてもかまわない。また、複素環基とは例えばフリル基、チエニル基、オキサゾリル基、ピリジル基、キノリル基、カルバゾリル基などの炭素以外の原子を有する環状構造基を示し、これは無置換でも置換されていてもかまわない。ハロゲンとはフッ素、塩素、臭素、ヨウ素を示す。ハロアルカン、ハロアルケン、ハロアルキンとは例えばトリフルオロメチル基などの、前述のアルキル基、アルケニル基、アルキニル基の一部あるいは全部が、前述のハロゲンで置換されたものを示し、残りの部分は無置換でも置換されていてもかまわない。アルデヒド基、カルボニル基、エステル基、カルバモイル基、アミノ基には脂肪族炭化水素、脂環式炭化水素、芳香族炭化水素、複素環などで置換されたものも含み、さらに脂肪族炭化水素、脂環式炭化水素、芳香族炭化水素、複素環は無置換でも置換されていてもかまわない。シリル基とは例えばトリメチルシリル基などのケイ素化合物基を示し、これは無置換でも置換されていてもかまわない。シロキサニル基とは例えばトリメチルシロキサニル基などのエーテル結合を介したケイ素化合物基を示し、これは無置換でも置換されていてもかまわない。また、隣接置換基との間に環構造を形成しても構わない。形成される環構造は無置換でも置換されていてもかまわない。
【００２３】
蛍光性骨格としては、後述の既知ホスト材料や従来から知られているドーパント材料の骨格が挙げられる。これらの蛍光性骨格がリンオキサイド基で置換されることで、電荷輸送性、薄膜形成性等が向上し、高輝度・高耐久性の発光素子を得ることが出来る。蛍光性骨格の中では、フェナンスリル、アントラニル、ピレニル、ペリレニル等の縮合芳香環が好適に用いられる。
【００２４】
上記のリンオキサイド基で置換された蛍光性骨格を有する有機蛍光体として、具体的には下記のような構造があげられる。
【００２５】
【化５】
【化６】
【化７】
料として用いてもかまわないが、優れた電子輸送能を有することから、ホスト材料として好適に用いられる。
【００２９】
発光材料のホスト材料はリンオキサイド基で置換された蛍光性骨格を有する有機蛍光体一種のみに限る必要はなく、複数のリンオキサイド基で置換された蛍光性骨格を有する有機蛍光体を混合して用いたり、既知のホスト材料の一種類以上をリンオキサイド基で置換された蛍光性骨格を有する有機蛍光体と混合して用いてもよい。既知のホスト材料としては特に限定されるものではないが、以前から発光体として知られていたアントラセン、フェナンスレン、ピレン、ペリレン、クリセンなどの縮合環誘導体、トリス（８−キノリノラト）アルミニウムを始めとするキノリノール誘導体の金属錯体、ベンズオキサゾール誘導体、スチルベン誘導体、ベンズチアゾール誘導体、チアジアゾール誘導体、チオフェン誘導体、テトラフェニルブタジエン誘導体、シクロペンタジエン誘導体、オキサジアゾール誘導体、ビススチリルアントラセン誘導体やジスチリルベンゼン誘導体などのビススチリル誘導体、キノリノール誘導体と異なる配位子を組み合わせた金属錯体、オキサジアゾール誘導体金属錯体、ベンズアゾール誘導体金属錯体、クマリン誘導体、ピロロピリジン誘導体、ペリノン誘導体、チアジアゾロピリジン誘導体、ポリマー系では、ポリフェニレンビニレン誘導体、ポリパラフェニレン誘導体、そして、ポリチオフェン誘導体などが使用できる。
【００３０】
発光材料に添加するドーパント材料は、特に限定されるものではないが、具体的には従来から知られている、フェナンスレン、アントラセン、ピレン、テトラセン、ペンタセン、ペリレン、ナフトピレン、ジベンゾピレン、ルブレンなどの縮合環誘導体、ベンズオキサゾール誘導体、ベンズチアゾール誘導体、ベンズイミダゾール誘導体、ベンズトリアゾール誘導体、オキサゾール誘導体、オキサジアゾール誘導体、チアゾール誘導体、イミダゾール誘導体、チアジアゾール誘導体、トリアゾール誘導体、ピラゾリン誘導体、スチルベン誘導体、チオフェン誘導体、テトラフェニルブタジエン誘導体、シクロペンタジエン誘導体、ビススチリルアントラセン誘導体やジスチリルベンゼン誘導体などのビススチリル誘導体、ジアザインダセン誘導体、フラン誘導体、ベンゾフラン誘導体、フェニルイソベンゾフラン、ジメシチルイソベンゾフラン、ジ（２−メチルフェニル）イソベンゾフラン、ジ（２−トリフルオロメチルフェニル）イソベンゾフラン、フェニルイソベンゾフランなどのイソベンゾフラン誘導体、ジベンゾフラン誘導体、７−ジアルキルアミノクマリン誘導体、７−ピペリジノクマリン誘導体、７−ヒドロキシクマリン誘導体、７−メトキシクマリン誘導体、７−アセトキシクマリン誘導体、３−ベンズチアゾリルクマリン誘導体、３−ベンズイミダゾリルクマリン誘導体、３−ベンズオキサゾリルクマリン誘導体などのクマリン誘導体、ジシアノメチレンピラン誘導体、ジシアノメチレンチオピラン誘導体、ポリメチン誘導体、シアニン誘導体、オキソベンズアンスラセン誘導体、キサンテン誘導体、ローダミン誘導体、フルオレセイン誘導体、ピリリウム誘導体、カルボスチリル誘導体、アクリジン誘導体、オキサジン誘導体、フェニレンオキサイド誘導体、キナクリドン誘導体、キナゾリン誘導体、ピロロピリジン誘導体、フロピリジン誘導体、１，２，５−チアジアゾロピレン誘導体、ペリノン誘導体、ピロロピロール誘導体、スクアリリウム誘導体、ビオラントロン誘導体、フェナジン誘導体、アクリドン誘導体、ジアザフラビン誘導体などがそのまま使用できるが、特にイソベンゾフラン誘導体が好適に用いられる。
【００３１】
また、ドーパント材料として上記蛍光性（一重項発光）材料だけでなく、燐光性（三重項発光）材料も好ましく用いられる。具体的には、ポルフィリン白金錯体やトリス（２−フェニルピリジル）イリジウム錯体、トリス｛２−（２−チオフェニル）ピリジル｝イリジウム錯体、トリス｛２−（２−ベンゾチオフェニル）ピリジル｝イリジウム錯体、トリス（２−フェニルベンゾチアゾール）イリジウム錯体、トリス（２−フェニルベンゾオキサゾール）イリジウム錯体、ベンゾキノリンイリジウム錯体などが挙げられるが、これらに限定されるものではない。
【００３２】
本発明において電子輸送性材料は、電界を与えられた電極間において陰極からの電子を効率良く輸送することが必要で、電子注入効率が高く、注入された電子を効率良く輸送することが望ましい。そのためには電子親和力が大きく、しかも電子移動度が大きく、さらに安定性に優れ、トラップとなる不純物が製造時および使用時に発生しにくい物質であることが要求される。しかしながら、正孔と電子のバランスを考えた場合に、陽極からの正孔が再結合せずに陰極側へ流れるのを効率よく阻止できる役割を主に果たす場合には、電子輸送能力がそれ程高くなくても、発光効率を向上させる効果は電子輸送能力が高い材料と同等に有する。したがって、本発明における電子輸送層は、正孔の移動を効率よく阻止できる正孔阻止層も同義のものとして含まれる。
【００３３】
このような条件を満たす物質として、本発明におけるリンオキサイド基で置換された蛍光性骨格を有する有機蛍光体が挙げられる。電子輸送材料はリンオキサイド基で置換された蛍光性骨格を有する有機蛍光体一種のみに限る必要はなく、複数のリンオキサイド基で置換された蛍光性骨格を有する有機蛍光体を混合して用いたり、既知の電子輸送材料の一種類以上をリンオキサイド基で置換された蛍光性骨格を有する有機蛍光体と混合して用いてもよい。既知の電子輸送材料としては、８−ヒドロキシキノリンアルミニウムに代表されるキノリノール誘導体金属錯体、トロポロン金属錯体、フラボノール金属錯体、ペリレン誘導体、ペリノン誘導体、ナフタレン、クマリン誘導体、オキサジアゾール誘導体、アルダジン誘導体、ビススチリル誘導体、ピラジン誘導体、フェナントロリン誘導体などがあるが特に限定されるものではない。これらの電子輸送材料は単独でも用いられるが、異なる電子輸送材料と積層または混合して使用しても構わない。
【００３４】
以上の正孔輸送層、発光層、電子輸送層に用いられる材料は単独で各層を形成することができるが、高分子結着剤としてポリ塩化ビニル、ポリカーボネート、ポリスチレン、ポリ（Ｎ−ビニルカルバゾール）、ポリメチルメタクリレート、ポリブチルメタクリレート、ポリエステル、ポリスルフォン、ポリフェニレンオキサイド、ポリブタジエン、炭化水素樹脂、ケトン樹脂、フェノキシ樹脂、ポリサルフォン、ポリアミド、エチルセルロース、酢酸ビニル、ＡＢＳ樹脂、ポリウレタン樹脂などの溶剤可溶性樹脂や、フェノール樹脂、キシレン樹脂、石油樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリコーン樹脂などの硬化性樹脂などに分散させて用いることも可能である。
【００３５】
本発明において発光物質の形成方法は、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、コーティング法など特に限定されるものではないが、通常は、抵抗加熱蒸着、電子ビーム蒸着が特性面で好ましい。層の厚みは、発光物質の抵抗値にもよるので限定することはできないが、１〜１０００ｎｍの間から選ばれる。
【００３６】
本発明において電気エネルギーとは主に直流電流を指すが、パルス電流や交流電流を用いることも可能である。電流値および電圧値は特に制限はないが、素子の消費電力、寿命を考慮するとできるだけ低いエネルギーで最大の輝度が得られるようにするべきである。
【００３７】
本発明においてマトリクスとは、表示のための画素が格子状に配置されたものをいい、画素の集合で文字や画像を表示する。画素の形状、サイズは用途によって決まる。例えばパソコン、モニター、テレビの画像および文字表示には、通常一辺が３００μｍ以下の四角形の画素が用いられるし、表示パネルのような大型ディスプレイの場合は、一辺がｍｍオーダーの画素を用いることになる。モノクロ表示の場合は、同じ色の画素を配列すればよいが、カラー表示の場合には、赤、緑、青の画素を並べて表示させる。この場合、典型的にはデルタタイプとストライプタイプがある。そして、このマトリクスの駆動方法としては、線順次駆動方法やアクティブマトリックスのどちらでもよい。線順次駆動の方が構造が簡単であるという利点があるが、動作特性を考慮した場合、アクティブマトリックスの方が優れる場合があるので、これも用途によって使い分けることが必要である。
【００３８】
本発明においてセグメントタイプとは、予め決められた情報を表示するようにパターンを形成し、決められた領域を発光させることになる。例えば、デジタル時計や温度計における時刻や温度表示、オーディオ機器や電磁調理器などの動作状態表示、自動車のパネル表示などがあげられる。そして、前記マトリクス表示とセグメント表示は同じパネルの中に共存していてもよい。
【００３９】
本発明においてバックライトとは、主に自発光しない表示装置の視認性を向上させる目的に使用され、液晶表示装置、時計、オーディオ機器、自動車パネル、表示板、標識などに使用される。特に液晶表示装置、中でも薄型化が課題となっているパソコン用途のバックライトとしては、従来方式のものが蛍光灯や導光板からなっているため薄型化が困難であることを考えると本発明におけるバックライトは、薄型、軽量が特徴になる。
【００４０】
【実施例】
以下、実施例および比較例をあげて本発明を説明するが、本発明はこれらの例によって限定されるものではない。
【００４１】
実施例１
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子（株）製、１５Ω／□、電子ビーム蒸着品）を３０×４０ｍｍに切断、エッチングを行った。得られた基板をアセトン、”セミコクリン５６”（フルウチ化学（株）製）で各々１５分間超音波洗浄してから、超純水で洗浄した。続いてイソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。この基板を素子を作製する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が５×１０-5Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔輸送材料として４，４’−ビス（Ｎ−（ｍ−トリル）−Ｎ−フェニルアミノ）ビフェニルを１００ｎｍ蒸着した。次に発光材料として、ジフェニル−２−ピレニルリンオキサイドを５０ｎｍの厚さに積層した。次に電子輸送材料として、２，９−ジメチル−４，７−ジフェニル−１，１０−フェナントロリン（ＢＴＣＰＮ）を１００ｎｍの厚さに積層した。次にリチウムを０．５ｎｍ有機層にドーピングした後、アルミニウムを２００ｎｍ蒸着して陰極とし、５×５ｍｍ角の素子を作製した。ここで言う膜厚は水晶発振式膜厚モニター表示値である。この発光素子からは、発光波長５２８ｎｍ、輝度５６５０カンデラ／平方メートルの高輝度青緑色発光が得られた。
【００４２】
比較例１
発光材料としてピレンを用いた他は実施例１と全く同様にして発光素子を作製した。この発光素子は短絡してしまい、発光を得ることができなかった。
【００４３】
実施例２
発光材料としてジフェニル−５−フェナンスレニルリンオキサイドを用いた他は実施例１と全く同様にして発光素子を作製した。この発光素子からは発光波長４８６ｎｍ、輝度４０１カンデラ／平方メートルの高色純度青色発光が得られた。
【００４４】
実施例３
発光材料として、ホスト材料として実施例１で用いたジフェニル−２−ピレニルリンオキサイドを、ドーパント材料としてペリレンを用いて、ドーパントが３ｗｔ％になるように５０ｎｍの厚さに共蒸着した他は実施例１と全く同様にして発光素子を作製した。この発光素子からは発光波長４６２，４９０ｎｍ（ダブルピーク）、輝度３１５０カンデラ／平方メートルの高輝度高色純度青色発光が得られた。
【００４５】
実施例４
電子輸送材料として、ジフェニル−２−ピレニルリンオキサイドを用いた他は実施例１と全く同様にして発光素子を作製した。実施例１に比べて、電子輸送性が向上し、同じ電流を流すのに必要な駆動電圧が３Ｖ低下した。
【００４６】
実施例５
発光材料として、ホスト材料として（８−キノリノラト）アルミニウム（III）（Ａｌｑ３）を、ドーパント材料として９−ベンゾチアゾール−２−イル−１，１，６，６−テトラメチル−２，３，５，６−テトラヒドロ−１Ｈ，４Ｈ−１１−オキサ−３ａ−アザ−ベンゾ［ｄｅ］アントラセン−１０−オン（クマリン５４５Ｔ）を用いた他は実施例４と全く同様にして発光素子を作製した。この発光素子からは発光波長５２０ｎｍ、輝度３００００カンデラ／平方メートルの高輝度高色純度緑色発光が得られた。この発光素子の通電後５００時間経過後の初期輝度保持率は８０％以上であり、均質な発光面を維持していた。
【００４７】
比較例３
電子輸送材料としてＢＴＣＰＮを用いた他は実施例５と全く同様にして発光素子を作製した。この発光素子の通電後５００時間経過後の初期輝度保持率は５０％以下であり、発光面にはムラが見られた。
【００４８】
実施例６
発光材料として、４，４’−ビス（２，２−ジフェニルビニル）ビフェニル（ＤＰＶＢｉ）を用いた他は実施例４と全く同様にして発光素子を作製した。この発光素子からは発光波長４６８ｎｍ、輝度１００００カンデラ／平方メートルの高輝度高色純度青色発光が得られた。
【００４９】
比較例３
電子輸送材料としてＡｌｑ３を用いた他は実施例６と全く同様にして発光素子を作製した。この発光素子からは発光材料だけでなく電子輸送材料も発光（緑色）し、色純度の悪い青色発光しか得られなかった。
【００５０】
実施例７
発光材料のうち、ホスト材料として３，６−ジビフェニル−２，５−ジ（３，５−ジｔ−ブチルベンジル）ピロロ［３，４−ｃ］ピロール−１，４−ジオンを、ドーパント材料として、４，４−ジフルオロ−１，３，５，７−テトラトリル−４−ボラ−３ａ，４ａ−ジアザ−インダセンを用いた他は実施例４と全く同様にして発光素子を作製した。この発光素子からは発光波長６３０ｎｍ、輝度８０００カンデラ／平方メートルの高輝度高色純度赤色発光が得られた。
【００５１】
比較例４
電子輸送材料としてＡｌｑ３を用いた他は実施例７と全く同様にして発光素子を作製した。この発光素子からは発光材料だけでなく電子輸送材料も発光（緑色）し、色純度の悪い赤色発光しか得られなかった。
【００５２】
実施例８
発光材料として、ホスト材料として４，４’ビス（９−カルバゾリル）ビフェニル（ＣＢＰ）を、ドーパント材料として、トリス（２−フェニルピリジル）イリジウム錯体を用いた他は実施例４と全く同様にして発光素子を作製した。この発光素子からは発光波長５２０ｎｍ、輝度５００００カンデラ／平方メートルの高輝度高色純度緑色発光が得られた。
【００５３】
実施例９
各有機層を蒸着するまでの工程は実施例１と同様に行った。抵抗加熱法によって、まず正孔輸送材料として４，４’−ビス（Ｎ−（ｍ−トリル）−Ｎ−フェニルアミノ）ビフェニルを１５０ｎｍ蒸着し、実施例１で用いたジフェニル−２−ピレニルリンオキサイドを５０ｎｍの厚さに蒸着した。次に電子輸送材料として、２，９−ジメチル−４，７−ジフェニル−１，１０−フェナントロリンを１００ｎｍの厚さに積層した。次にリチウムを０．５ｎｍ有機層にドーピングした後、アルミニウムを２００ｎｍ蒸着して５×５ｍｍ角の素子を作製した。ここでいう膜厚は水晶発振式膜厚モニター表示値である。この発光素子を真空セル内で１ｍＡパルス駆動（Ｄｕｔｙ比１／６０、パルス時の電流値６０ｍＡ）させたところ、良好な発光が確認された。
【００５４】
実施例１０
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子（株）製、１５Ω／□、電子ビーム蒸着品）を３０×４０ｍｍに切断、フォトリソグラフィ法によって３００μmピッチ（残り幅２７０μm）×３２本のストライプ状にパターン加工した。ＩＴＯストライプの長辺方向片側は外部との電気的接続を容易にするために１．２７ｍｍピッチ（開口部幅８００μm）まで広げてある。得られた基板をアセトン、”セミコクリン５６”で各々１５分間超音波洗浄してから、超純水で洗浄した。続いてイソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。この基板を素子を作製する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が５×１０-4Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔輸送材料として４，４’−ビス（Ｎ−（ｍ−トリル）−Ｎ−フェニルアミノ）ビフェニルを１５０ｎｍ蒸着し、実施例１で用いたジフェニル−２−ピレニルリンオキサイドを５０ｎｍの厚さに蒸着した。次に電子輸送材料として、２，９−ジメチル−４，７−ジフェニル−１，１０−フェナントロリンを１００ｎｍの厚さに積層した。ここで言う膜厚は水晶発振式膜厚モニター表示値である。次に厚さ５０μｍのコバール板にウエットエッチングによって１６本の２５０μmの開口部（残り幅５０μm、３００μmピッチに相当）を設けたマスクを、真空中でＩＴＯストライプに直交するようにマスク交換し、マスクとＩＴＯ基板が密着するように裏面から磁石で固定した。そしてリチウムを０．５ｎｍ有機層にドーピングした後、アルミニウムを２００ｎｍ蒸着して３２×１６ドットマトリクス素子を作製した。本素子をマトリクス駆動させたところ、クロストークなく文字表示できた。
【００５５】
【発明の効果】
本発明は、発光効率が高く、色純度に優れた、発光素子を提供できるものである。特に青色発光にとって有効なものである。[0001]
BACKGROUND OF THE INVENTION
The present invention is an element that can convert electrical energy into light, and can be used in the fields of display elements, flat panel displays, backlights, lighting, interiors, signs, signboards, electrophotographic machines, optical signal generators, and the like. It relates to an element.
[0002]
[Prior art]
In recent years, research on an organic laminated thin film light emitting device in which light is emitted when electrons injected from a cathode and holes injected from an anode are recombined in an organic phosphor sandwiched between both electrodes has been actively conducted. This element is attracting attention because it is thin, has high luminance emission under a low driving voltage, and multicolor emission by selecting a fluorescent material.
[0003]
This study was conducted by C.D. W. Since Tang et al. Have shown that organic laminated thin-film elements emit light with high brightness (Appl. Phys. Lett. 51 (12) 21, p. 913, 1987), many research institutions have studied. A typical structure of an organic laminated thin film light emitting device presented by a research group of Kodak Company is a hole transporting diamine compound on an ITO glass substrate, 8-hydroxyquinoline aluminum as a light emitting layer, and Mg: Ag as a cathode. They were sequentially provided, and green light emission of 1000 cd / m 2 was possible with a driving voltage of about 10V. Some organic multilayer thin film light emitting elements have different configurations such as those provided with an electron transport layer in addition to the above-described element constituent elements, but basically follow the configuration of Kodak Company.
[0004]
The light emitting layer is composed of only a host material or is formed by doping a host material with a guest material. Light emitting materials are required to have three primary colors, but the green light emitting materials have been most researched so far. At present, intensive research is being conducted to improve the characteristics of red and blue light-emitting materials. In particular, a blue light emitting material that can emit light with high luminance and good color purity is desired.
[0005]
As host materials, metal complexes of quinolinol derivatives such as the aforementioned tris (8-quinolinolato) aluminum, benzoxazole derivatives, stilbene derivatives, benzthiazole derivatives, thiadiazole derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, Examples thereof include oxadiazole derivatives, oxadiazole derivative metal complexes, and benzazole derivative metal complexes.
[0006]
Examples of blue light-emitting host materials that have achieved relatively good performance include metal complexes combining a quinolinol derivative and a different ligand (Japanese Patent Laid-Open No. 5-214332), and bisstyrylbenzene derivatives (Japanese Patent Laid-Open No. 4). -117485), but the color purity is not particularly satisfactory.
[0007]
On the other hand, a dopant material as a guest material is known to be useful as a laser dye, and coumarin derivatives such as 7-dimethylamino-4-methylcoumarin, and condensed aromatic rings such as perylene, pyrene and anthracene. Derivatives, stilbene derivatives, oligophenylene derivatives, furan derivatives, quinolone derivatives, oxazole derivatives, oxadiazole derivatives and the like are known.
[0008]
[Problems to be solved by the invention]
However, many of the light emitting materials (host materials and dopant materials) used in the prior art have low light emission efficiency and high power consumption, and low durability and short device lifetime. Further, red, green, and blue primary light emission is required for full-color displays. However, in red and blue light emission, there are few that satisfy the emission wavelength, and there are few that have a wide emission peak width and good color purity. In particular, in blue light emission, those having excellent durability and sufficient luminance and color purity characteristics are required.
[0009]
Conventionally, even if a few existing materials are used, a desired luminescent color cannot be obtained or a high-efficiency luminescence can be obtained due to the interaction with the luminescent material or the mixed emission of the electron transport material itself. There were problems such as short durability. For example, in JP-A-5-331459, a specific phenanthroline derivative is used as an electron transport material. However, although it exhibits high-efficiency light emission, there is a problem in that it is crystallized by energization for a long time and has extremely short durability. In addition, there are quinolinol metal complexes and benzoquinolinol metal complexes that exhibit relatively good characteristics in terms of luminous efficiency and durability, but these materials themselves have a high blue-green to yellow light-emitting ability. When used as a transport material, the light purity of these materials themselves may be mixed to deteriorate the color purity.
[0010]
The object of the present invention is to solve such problems of the prior art and to provide a light emitting device having high luminous efficiency, high luminance and excellent color purity.
[0011]
[Means for Solving the Problems]
The present invention is a device in which a luminescent substance is present between an anode and a cathode and emits light by electric energy, and the device includes an organic phosphor having a fluorescent skeleton substituted with a phosphate group. It is the light emitting element which does.
[0012]
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, if the anode is transparent for extracting light, a conductive metal oxide such as tin oxide, indium oxide and indium tin oxide (ITO), or a metal such as gold, silver and chromium, copper iodide, sulfide Inorganic conductive materials such as copper and conductive polymers such as polythiophene, polypyrrole, and polyaniline are not particularly limited, but it is particularly desirable to use ITO glass or Nesa glass. The resistance of the transparent electrode is not limited as long as a current sufficient for light emission of the element can be supplied, but it is desirable that the resistance be low from the viewpoint of power consumption of the element. For example, an ITO substrate of 300 Ω / □ or less functions as an element electrode. However, since it is now possible to supply a substrate of about 10 Ω / □, it is particularly desirable to use a low resistance product. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm. Further, soda lime glass, non-alkali glass or the like is used for the glass substrate, and the thickness of the glass substrate only needs to be sufficient to maintain the mechanical strength, so 0.5 mm or more is sufficient. As for the glass material, alkali-free glass is preferred because it is better that there are fewer ions eluted from the glass, but soda-lime glass with a barrier coat such as SiO 2 is also commercially available and can be used. The ITO film forming method is not particularly limited, such as an electron beam method, a sputtering method, or a chemical reaction method.
[0013]
In the present invention, the cathode is not particularly limited as long as it can efficiently inject electrons into the organic layer, but is generally platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, chromium, lithium, sodium, potassium. Calcium, magnesium, etc. can be mentioned, but lithium, sodium, potassium, calcium, magnesium or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics. However, these low work function metals are generally unstable in the atmosphere. For example, the organic layer is doped with a small amount of lithium, cesium, or magnesium (1 nm or less in the thickness gauge display of vacuum deposition). A method using a highly stable electrode can be mentioned as a preferable example, but an inorganic salt such as lithium fluoride can also be used, and the method is not particularly limited thereto. Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum, indium, or alloys using these metals, and inorganic substances such as silica, titania, silicon nitride, polyvinyl alcohol, vinyl chloride, Preferred examples include laminating hydrocarbon polymers. The method for producing these electrodes is not particularly limited as long as conduction can be achieved such as resistance heating, electron beam, sputtering, ion plating, and coating.
[0014]
In the present invention, the light-emitting substance is 1) a hole transport layer / light-emitting layer, 2) a hole transport layer / light-emitting layer / electron transport layer, 3) a light-emitting layer / electron transport layer, and 4) a combination of the above. Any of the forms mixed in a single layer may be used. That is, as the element structure, in addition to the multilayer laminated structure of the above 1) to 3), only the light emitting material alone or a layer containing the light emitting material and the hole transport material or electron transport material may be provided as in 4). Furthermore, the luminescent substance in the present invention corresponds to both a substance that emits light by itself and a substance that assists the light emission, and refers to a compound, a layer, or the like that is involved in light emission.
[0015]
In the present invention, the hole transport layer is formed by laminating and mixing a hole transport material alone or two or more kinds of materials, or a mixture of a hole transport material and a polymer binder. As a hole transporting material, it is necessary to efficiently transport holes from the anode between electrodes to which an electric field is applied, and it is desirable that the hole injection efficiency is high and the injected holes are transported efficiently. . For this purpose, it is required that the ionization potential is low, the hole mobility is high, the stability is high, and the trapping impurities are difficult to be generated during production and use. Although it does not specifically limit as a substance which satisfy | fills such conditions, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'-diphenyl-1,1'- Triphenylamines such as diamine, N, N′-dinaphthyl-N, N′-diphenyl-4,4′-diphenyl-1,1′-diamine, bis (N-allylcarbazole) or bis (N-alkylcarbazole) ), Pyrazoline derivatives, stilbene compounds, hydrazone compounds, oxadiazole derivatives, phthalocyanine derivatives, heterocyclic compounds typified by porphyrin derivatives, in the case of polymers, polycarbonates and styrene derivatives having polyvinyl monomers in the side chain, polyvinyl Carbazole, polysilane, etc. are preferred, but a thin film necessary for device fabrication can be formed and holes can be injected from the anode It is not particularly limited as long as it is a compound capable of transporting holes to al.
[0016]
The light emitting material in the present invention may be either a host material alone or a combination of a host material and a dopant material. Further, the dopant material may be included in the entire host material, or may be included partially. The dopant material may be either laminated or dispersed.
[0017]
In the present invention, the light emitting material includes an organic phosphor having a fluorescent skeleton substituted with a phosphorus oxide group. In addition, specific examples of the organic phosphor having a fluorescent skeleton substituted with a phosphate group in the present invention include compounds represented by the following general formula (1) or (2).
[0018]
[Chemical 3]
R 1 to R 3 are each hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group. , Aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group . Further, at least one of R 1 to R 3 is a fluorescent skeleton.
[0020]
[Formula 4]
Here, R 4 to R 5 are each hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group. , Aryl group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, carbamoyl group, amino group, nitro group, silyl group, siloxanyl group . X represents a fluorescent skeleton. n represents a natural number of 2 or more.
[0022]
Among these substituents, the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, and the like, which may be unsubstituted or substituted. The aralkyl group is an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. It doesn't matter. The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group or a butadienyl group, which may be unsubstituted or substituted. The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be unsubstituted or substituted. . The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond such as an acetylenyl group, which may be unsubstituted or substituted. The alkoxy group refers to an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom. The aryl ether group refers to an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. The arylthioether group is a group in which the oxygen atom of the ether bond of the arylether group is substituted with a sulfur atom. The aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group, which may be unsubstituted or substituted. The heterocyclic group is a cyclic structural group having an atom other than carbon, such as a furyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolyl group, or a carbazolyl group, which may be unsubstituted or substituted. Absent. Halogen is fluorine, chlorine, bromine or iodine. Haloalkane, haloalkene, haloalkyne means, for example, a part or all of the above-mentioned alkyl group, alkenyl group, alkynyl group such as trifluoromethyl group substituted with the above-mentioned halogen, and the remaining part may be unsubstituted It may be replaced. Aldehyde groups, carbonyl groups, ester groups, carbamoyl groups, amino groups include those substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic rings, etc. The cyclic hydrocarbon, aromatic hydrocarbon and heterocyclic ring may be unsubstituted or substituted. A silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The siloxanyl group refers to a silicon compound group via an ether bond such as a trimethylsiloxanyl group, which may be unsubstituted or substituted. A ring structure may be formed between adjacent substituents. The ring structure formed may be unsubstituted or substituted.
[0023]
Examples of the fluorescent skeleton include known host materials described later and skeletons of conventionally known dopant materials. By substituting these fluorescent skeletons with a phosphorus oxide group, charge transportability, thin film formation properties, etc. are improved, and a light-emitting element with high luminance and high durability can be obtained. Among the fluorescent skeletons, condensed aromatic rings such as phenanthryl, anthranyl, pyrenyl, and perylenyl are preferably used.
[0024]
Specific examples of the organic phosphor having a fluorescent skeleton substituted with the above-mentioned phosphorus oxide group include the following structures.
[0025]
[Chemical formula 5]
[Chemical 6]
[Chemical 7]
Although it may be used as a material, since it has an excellent electron transport ability, it is preferably used as a host material.
[0029]
The host material of the light emitting material need not be limited to a single organic phosphor having a fluorescent skeleton substituted with a phosphorus oxide group, and a mixture of organic phosphors having a fluorescent skeleton substituted with a plurality of phosphoroxide groups. Alternatively, one or more types of known host materials may be mixed with an organic phosphor having a fluorescent skeleton substituted with a phosphorus oxide group. Although it does not specifically limit as a known host material, Condensed ring derivatives, such as anthracene, phenanthrene, pyrene, perylene, chrysene, etc. which were known as a light emitter for a long time, Tris (8-quinolinolato) aluminum etc. are included. Metal complexes of quinolinol derivatives, benzoxazole derivatives, stilbene derivatives, benzthiazole derivatives, thiadiazole derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, oxadiazole derivatives, bisstyrylanthracene derivatives and distyrylbenzene derivatives , Metal complexes combining quinolinol derivatives with different ligands, oxadiazole derivative metal complexes, benzazole derivative metal complexes, coumarin derivatives, pyrrolopyridine derivatives , Perinone derivatives, thiadiazolopyridine derivatives, the polymer system, polyphenylene vinylene derivatives, polyparaphenylene derivatives, and polythiophene derivatives may be used.
[0030]
The dopant material added to the light emitting material is not particularly limited, but specifically, conventionally known condensations such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, etc. Ring derivatives, benzoxazole derivatives, benzthiazole derivatives, benzimidazole derivatives, benztriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenyl Butadiene derivatives, cyclopentadiene derivatives, bisstyryl anthracene derivatives, distyrylbenzene derivatives and other bisstyryl derivatives, diazaindacene derivatives Body, furan derivative, benzofuran derivative, phenylisobenzofuran, dimesitylisobenzofuran, di (2-methylphenyl) isobenzofuran, di (2-trifluoromethylphenyl) isobenzofuran, isobenzofuran derivatives such as phenylisobenzofuran, dibenzofuran Derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzthiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives , Coumarin derivatives such as 3-benzoxazolyl coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzan Lathene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazo Lopylene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, diazaflavin derivatives and the like can be used as they are, and isobenzofuran derivatives are particularly preferably used.
[0031]
As the dopant material, not only the fluorescent (singlet light emission) material but also a phosphorescent (triplet light emission) material is preferably used. Specifically, porphyrin platinum complex, tris (2-phenylpyridyl) iridium complex, tris {2- (2-thiophenyl) pyridyl} iridium complex, tris {2- (2-benzothiophenyl) pyridyl} iridium complex, tris Examples include (2-phenylbenzothiazole) iridium complex, tris (2-phenylbenzoxazole) iridium complex, benzoquinoline iridium complex, and the like, but are not limited thereto.
[0032]
In the present invention, the electron transporting material needs to efficiently transport electrons from the cathode between electrodes to which an electric field is applied, and it is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently. For this purpose, it is required that the material has a high electron affinity, a high electron mobility, excellent stability, and a substance that does not easily generate trapping impurities during manufacturing and use. However, considering the balance between holes and electrons, if the role of effectively preventing the holes from the anode from flowing to the cathode side without recombination is mainly played, the electron transport capability is so high. Even if not, the effect of improving the luminous efficiency is equivalent to that of a material having a high electron transport capability. Therefore, the electron transport layer in the present invention includes a hole blocking layer that can efficiently block the movement of holes as the same meaning.
[0033]
Examples of the substance that satisfies such conditions include organic phosphors having a fluorescent skeleton substituted with a phosphorus oxide group in the present invention. The electron transport material need not be limited to a single organic phosphor having a fluorescent skeleton substituted with a phosphorus oxide group, and may be a mixture of organic phosphors having a fluorescent skeleton substituted with a plurality of phosphorus oxide groups. One or more kinds of known electron transport materials may be mixed with an organic phosphor having a fluorescent skeleton substituted with a phosphorus oxide group. Known electron transport materials include quinolinol derivative metal complexes represented by 8-hydroxyquinoline aluminum, tropolone metal complexes, flavonol metal complexes, perylene derivatives, perinone derivatives, naphthalene, coumarin derivatives, oxadiazole derivatives, aldazine derivatives, bisstyryl. Although there are derivatives, pyrazine derivatives, phenanthroline derivatives, etc., there is no particular limitation. These electron transport materials are used alone, but may be laminated or mixed with different electron transport materials.
[0034]
The materials used for the hole transport layer, the light emitting layer, and the electron transport layer can form each layer alone. Polyvinyl chloride, polycarbonate, polystyrene, poly (N-vinylcarbazole) are used as the polymer binder. Solvent-soluble resins such as polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polysulfone, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane resin, It can also be used by being dispersed in a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, or silicone resin.
[0035]
In the present invention, the method for forming the luminescent material is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, coating method, etc., but resistance heating vapor deposition and electron beam vapor deposition are usually in terms of characteristics. preferable. The thickness of the layer depends on the resistance value of the luminescent material and cannot be limited, but is selected from 1 to 1000 nm.
[0036]
In the present invention, electrical energy mainly refers to a direct current, but a pulse current or an alternating current can also be used. The current value and the voltage value are not particularly limited, but the maximum luminance should be obtained with the lowest possible energy in consideration of the power consumption and lifetime of the element.
[0037]
In the present invention, the matrix refers to a matrix in which pixels for display are arranged in a grid pattern, and a character or image is displayed by a set of pixels. The shape and size of the pixel are determined by the application. For example, a rectangular pixel with a side of 300 μm or less is normally used for displaying images and characters on a personal computer, monitor, television, etc. In a large display such as a display panel, a pixel with a side of mm order is used. . In monochrome display, pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. The line-sequential driving has an advantage that the structure is simple. However, the active matrix may be superior in consideration of the operation characteristics, so that it is necessary to properly use it depending on the application.
[0038]
In the present invention, the segment type means that a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation status display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be given. The matrix display and the segment display may coexist in the same panel.
[0039]
In the present invention, the backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display board, a sign, and the like. In particular, as a backlight for a liquid crystal display device, in particular, a personal computer application for which thinning is an issue, it is difficult to reduce the thickness of the conventional method because it is made of a fluorescent lamp or a light guide plate. The backlight is thin and lightweight.
[0040]
【Example】
EXAMPLES Hereinafter, although an Example and a comparative example are given and this invention is demonstrated, this invention is not limited by these examples.
[0041]
Example 1
A glass substrate on which an ITO transparent conductive film was deposited to a thickness of 150 nm (Asahi Glass Co., Ltd., 15Ω / □, electron beam evaporated product) was cut into 30 × 40 mm and etched. The obtained substrate was ultrasonically washed with acetone and “Semicocrine 56” (manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, respectively, and then washed with ultrapure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes to dry. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −5 Pa or less. First, 4,4′-bis (N- (m-tolyl) -N-phenylamino) biphenyl was deposited as a hole transport material by a resistance heating method to a thickness of 100 nm. Next, as a light emitting material, diphenyl-2-pyrenyl phosphorus oxide was laminated to a thickness of 50 nm. Next, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BTCPN) was laminated to a thickness of 100 nm as an electron transport material. Next, after doping the organic layer with 0.5 nm of lithium, aluminum was vapor-deposited with a thickness of 200 nm to form a 5 × 5 mm square device. The film thickness referred to here is a display value of a crystal oscillation type film thickness monitor. From this light-emitting element, high-luminance blue-green light emission with an emission wavelength of 528 nm and a luminance of 5650 candela / square meter was obtained.
[0042]
Comparative Example 1
A light emitting device was fabricated in the same manner as in Example 1 except that pyrene was used as the light emitting material. This light emitting element was short-circuited, and light emission could not be obtained.
[0043]
Example 2
A light emitting device was fabricated in exactly the same manner as in Example 1 except that diphenyl-5-phenanthrenyl phosphorus oxide was used as the light emitting material. From this light emitting element, high color purity blue light emission with an emission wavelength of 486 nm and a luminance of 401 candela / square meter was obtained.
[0044]
Example 3
The procedure was carried out except that diphenyl-2-pyrenyl phosphorus oxide used in Example 1 was used as the light emitting material in Example 1 and perylene was used as the dopant material, so that the dopant content was 3 wt%, so that the thickness was 50 nm. A light emitting device was fabricated in exactly the same manner as in Example 1. From this light-emitting element, high-luminance, high-color purity blue light emission having an emission wavelength of 462, 490 nm (double peak) and a luminance of 3150 candela / square meter was obtained.
[0045]
Example 4
A light emitting device was produced in the same manner as in Example 1 except that diphenyl-2-pyrenyl phosphorus oxide was used as the electron transport material. Compared with Example 1, the electron transporting property was improved, and the driving voltage required to flow the same current was reduced by 3V.
[0046]
Example 5
As a light-emitting material, (8-quinolinolato) aluminum (III) (Alq3) is used as a host material, and 9-benzothiazol-2-yl-1,1,6,6-tetramethyl-2,3,5,5 is used as a dopant material. A light emitting device was fabricated in the same manner as in Example 4 except that 6-tetrahydro-1H, 4H-11-oxa-3a-aza-benzo [de] anthracen-10-one (coumarin 545T) was used. From this light emitting element, high luminance high color purity green light emission having an emission wavelength of 520 nm and a luminance of 30000 candela / square meter was obtained. The initial luminance retention after 500 hours from the energization of this light emitting element was 80% or more, and a uniform light emitting surface was maintained.
[0047]
Comparative Example 3
A light emitting device was fabricated in the same manner as in Example 5 except that BTCPN was used as the electron transport material. The initial luminance retention after 500 hours passed after the light-emitting element was energized was 50% or less, and unevenness was observed on the light-emitting surface.
[0048]
Example 6
A light emitting device was fabricated in exactly the same manner as in Example 4 except that 4,4′-bis (2,2-diphenylvinyl) biphenyl (DPVBi) was used as the light emitting material. From this light-emitting element, high-luminance, high-color-purity blue light emission having an emission wavelength of 468 nm and a luminance of 10,000 candela / square meter was obtained.
[0049]
Comparative Example 3
A light emitting device was fabricated in exactly the same manner as in Example 6 except that Alq3 was used as the electron transport material. From this light emitting element, not only the light emitting material but also the electron transporting material emitted light (green), and only blue light emission with poor color purity was obtained.
[0050]
Example 7
Among the light-emitting materials, 3,6-dibiphenyl-2,5-di (3,5-di-t-butylbenzyl) pyrrolo [3,4-c] pyrrole-1,4-dione is used as a dopant material as a host material. As described in Example 4, except that 4,4-difluoro-1,3,5,7-tetratolyl-4-bora-3a, 4a-diaza-indacene was used, a light emitting device was fabricated. From this light emitting element, high luminance, high color purity red light emission having an emission wavelength of 630 nm and a luminance of 8000 candela / square meter was obtained.
[0051]
Comparative Example 4
A light emitting device was fabricated in the same manner as in Example 7 except that Alq3 was used as the electron transport material. From this light emitting element, not only the light emitting material but also the electron transporting material emitted light (green), and only red light emission with poor color purity was obtained.
[0052]
Example 8
Light emission was performed in the same manner as in Example 4 except that 4,4′bis (9-carbazolyl) biphenyl (CBP) was used as the light emitting material, and tris (2-phenylpyridyl) iridium complex was used as the dopant material. An element was produced. From this light emitting element, high luminance high color purity green light emission with an emission wavelength of 520 nm and a luminance of 50000 candela / square meter was obtained.
[0053]
Example 9
The process until each organic layer was deposited was performed in the same manner as in Example 1. First, 4,4′-bis (N- (m-tolyl) -N-phenylamino) biphenyl was deposited as a hole transport material by a resistance heating method to a thickness of 150 nm, and the diphenyl-2-pyrenyl phosphorus used in Example 1 was used. Oxide was evaporated to a thickness of 50 nm. Next, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline was laminated to a thickness of 100 nm as an electron transport material. Next, after doping lithium with a 0.5 nm organic layer, aluminum was vapor-deposited with a thickness of 200 nm to produce a 5 × 5 mm square device. The film thickness here is a display value of the crystal oscillation type film thickness monitor. When this light-emitting element was driven in a vacuum cell by 1 mA pulse (Duty ratio 1/60, pulsed current value 60 mA), good light emission was confirmed.
[0054]
Example 10
A glass substrate (manufactured by Asahi Glass Co., Ltd., 15Ω / □, electron beam evaporation product) on which ITO transparent conductive film is deposited by 150 nm is cut into 30 × 40 mm, and 300 μm pitch (remaining width 270 μm) × 32 stripes by photolithography. Patterned into a shape. One side of the ITO stripe in the long side direction is expanded to a pitch of 1.27 mm (opening width 800 μm) in order to facilitate electrical connection with the outside. The obtained substrate was ultrasonically washed with acetone and “Semicocrine 56” for 15 minutes, respectively, and then washed with ultrapure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes to dry. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −4 Pa or less. First, 4,4′-bis (N- (m-tolyl) -N-phenylamino) biphenyl was deposited as a hole transport material by a resistance heating method to a thickness of 150 nm, and the diphenyl-2-pyrenyl phosphorus used in Example 1 was used. Oxide was evaporated to a thickness of 50 nm. Next, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline was laminated to a thickness of 100 nm as an electron transport material. The film thickness referred to here is a display value of a crystal oscillation type film thickness monitor. Next, the mask with 16 μm openings (corresponding to the remaining width of 50 μm and 300 μm pitch) formed by wet etching on the 50 μm thick Kovar plate was replaced in a vacuum so as to be orthogonal to the ITO stripe. And it fixed with the magnet from the back so that an ITO board | substrate might closely_contact | adhere. And after doping lithium with a 0.5 nm organic layer, aluminum was vapor-deposited 200 nm, and the 32 * 16 dot matrix element was produced. When this element was driven in matrix, characters could be displayed without crosstalk.
[0055]
【Effect of the invention】
The present invention can provide a light emitting element having high luminous efficiency and excellent color purity. This is particularly effective for blue light emission.
Claims (2)
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| EP2860782A1 (en) | 2013-10-09 | 2015-04-15 | Novaled GmbH | Semiconducting material comprising a phosphine oxide matrix and metal salt |
| EP2887416A1 (en) | 2013-12-23 | 2015-06-24 | Novaled GmbH | N-doped semiconducting material comprising phosphine oxide matrix and metal dopant |
| EP2887412A1 (en) | 2013-12-23 | 2015-06-24 | Novaled GmbH | Semiconducting material |
| EP3079179A1 (en) | 2015-04-08 | 2016-10-12 | Novaled GmbH | Semiconducting material comprising a phosphine oxide matrix and metal salt |
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|---|---|---|---|---|
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Family Cites Families (3)
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|---|---|---|---|---|
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-
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