JP4871464B2 - Organic light emitting device - Google Patents

Description

【００１２】
また本発明は、
陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記一般式［ＩＩ］で示される縮合多環化合物の少なくとも一種を含有することを特徴とする有機発光素子を提供する。
【００１３】
一般式［ＩＩ］
【外１５】

【００１４】
（式中、Ｒ_５、Ｒ _６ は、いずれも水素原子である。Ｒ _７ は水素原子あるいはピリジニル基である。
Ａｒ_３、Ａｒ _４ はいずれもフルオランテニル基であり、いずれの前記フルオランテニル基も一般式［ＩＩ］に示されるベンゼン環に８位で結合する。
Ａｒ _５ は、ピレニル基、一般式［ＩＩ］に示されるベンゼン環に８位で結合するフルオランテニル基、フェナントレニル基、テトラセニル基、ペリレニル基のいずれかである。）
また本発明は、
陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記一般式［ＩＩＩ］で示される縮合多環化合物の少なくとも一種を含有することを特徴とする有機発光素子を提供する。
【００１５】
一般式［ＩＩＩ］
【外１６】

【００１６】
（式中、Ｒ_８およびＲ_９ は、いずれも水素原子である。
Ａｒ _６ 、Ａｒ _７ は、いずれもフルオランテニル基であり、いずれの前記フルオランテニル基も一般式［ＩＩＩ］に示されるベンゼン環に８位で結合する。前記フルオランテニル基はフェニル基を有してもよい。
Ａｒ _８ およびＡｒ _９ はそれぞれ独立にアントラセニル基、一般式［ＩＩＩ］に示されるベンゼン環に８位で結合するフルオランテニル基、ペンタセニル基、ナフチル基から選ばれる。前記アントラセニル基と前記ナフチル基はアルキル基を有してもよい。）
また本発明は、
陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記構造式で示される縮合多環化合物を含有することを特徴とする有機発光素子を提供する。
【００１７】
【外１５】

【００１８】
また本発明は、
陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記構造式で示される縮合多環化合物を含有することを特徴とする有機発光素子を提供する。
【００１９】
【外１６】

【００２０】
また本発明は、
陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記構造式で示されるいずれかの縮合多環化合物を含有することを特徴とする有機発光素子を提供する。
【００２１】
【外１７】

【外１８】

【００２２】
また本発明は、
陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記構造式で示されるいずれかの縮合多環化合物を含有することを特徴とする有機発光素子を提供する。
【００２３】
【外１９】

【外２０】

【外２１】

【外２２】

【００２５】
【発明の実施の形態】
本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記一般式［Ｉ］で示される縮合多環化合物の少なくとも一種を含有することを特徴とする。
【００２６】
一般式［Ｉ］
【外２１】

【００２７】
（式中、Ｒ_１、Ｒ_２、Ｒ_３およびＲ_４は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。Ｒ_１、Ｒ_２、Ｒ_３およびＲ_４は、同じであっても異なっていてもよい。Ａｒ_１およびＡｒ_２は、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、Ａｒ_１およびＡｒ_２の少なくとも１つはフルオランテニル基を表わす。Ａｒ_１およびＡｒ_２は、同じであっても異なっていてもよい。）
また本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記一般式［ＩＩ］で示される縮合多環化合物の少なくとも一種を含有することを特徴とする。
【００２８】
一般式［ＩＩ］
【外２２】

【００２９】
（式中、Ｒ_５、Ｒ_６およびＲ_７は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。Ｒ_５、Ｒ_６およびＲ_７は、同じであっても異なっていてもよい。Ａｒ_３、Ａｒ_４およびＡｒ_５は、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、Ａｒ_３、Ａｒ_４およびＡｒ_５の少なくとも１つは置換あるいは無置換のフルオランテニル基を表わす。Ａｒ_３、Ａｒ_４およびＡｒ_５は、同じであっても異なっていてもよい。）
また本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記一般式［ＩＩＩ］で示される縮合多環化合物の少なくとも一種を含有することを特徴とする。
【００３０】
一般式［ＩＩＩ］
【外２３】

【００３１】
（式中、Ｒ_８およびＲ_９は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。Ｒ_８およびＲ_９は、同じであっても異なっていてもよい。Ａｒ_６、Ａｒ_７、Ａｒ_８およびＡｒ_９は、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、Ａｒ_６、Ａｒ_７、Ａｒ_８およびＡｒ_９の少なくとも１つは置換あるいは無置換のフルオランテニル基を表わす。Ａｒ_６、Ａｒ_７、Ａｒ_８およびＡｒ_９は、同じであっても異なっていてもよい。）
また本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記一般式［ＩＶ］で示される縮合多環化合物の少なくとも一種を含有することを特徴とする。
【００３２】
一般式［ＩＶ］
【外２４】

【００３３】
（式中、Ｒ_１０、Ｒ_１１、Ｒ_１２およびＲ_１３は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。Ｒ_１０、Ｒ_１１、Ｒ_１２およびＲ_１３は、同じであっても異なっていてもよい。Ａｒ_１０およびＡｒ_１１は、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、Ａｒ_１０およびＡｒ_１１の少なくとも１つは置換あるいは無置換のフルオランテニル基を表わす。Ａｒ_１０およびＡｒ_１１は、同じであっても異なっていてもよい。）
また本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記一般式［Ｖ］で示される縮合多環化合物の少なくとも一種を含有することを特徴とする。
【００３４】
一般式［Ｖ］
【外２５】

【００３５】
（式中、Ｒ_１４、Ｒ_１５およびＲ_１６は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。Ｒ_１４、Ｒ_１５およびＲ_１６は、同じであっても異なっていてもよい。Ａｒ_１２、Ａｒ_１３およびＡｒ_１４は、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、Ａｒ_１２、Ａｒ_１３およびＡｒ_１４の少なくとも１つは置換あるいは無置換のフルオランテニル基を表わす。Ａｒ_１２、Ａｒ_１３およびＡｒ_１４は、同じであっても異なっていてもよい。）
また本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記一般式［ＶＩ］で示される縮合多環化合物の少なくとも一種を含有することを特徴とする。
【００３６】
一般式［ＶＩ］
【外２６】

【００３７】
（式中、Ｒ_１７およびＲ_１８は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。Ｒ_１７およびＲ_１８は、同じであっても異なっていてもよい。Ａｒ_１５、Ａｒ_１６、Ａｒ_１７およびＡｒ_１８は、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、Ａｒ_１５、Ａｒ_１６、Ａｒ_１７およびＡｒ_１８の少なくとも１つは置換あるいは無置換のフルオランテニル基を表わす。Ａｒ_１５、Ａｒ_１６、Ａｒ_１７およびＡｒ_１８は、同じであっても異なっていてもよい。）
また本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物からなる層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記一般式［ＶＩＩ］で示される縮合多環化合物の少なくとも一種を含有することを特徴とする。
【００３８】
一般式［ＶＩＩ］
【外２７】

【００３９】
（式中、Ａｒ_１９、Ａｒ_２０、Ａｒ_２１、Ａｒ_２２、Ａｒ_２３およびＡｒ_２４は、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、Ａｒ_１５、Ａｒ_１６、Ａｒ_１７およびＡｒ_１８の少なくとも１つは置換あるいは無置換のフルオランテニル基を表わす。Ａｒ_１５、Ａｒ_１６、Ａｒ_１７およびＡｒ_１８同じであっても異なっていてもよい。）
本発明の有機発光素子は、一般式［Ｉ］〜一般式［ＶＩＩ］のＡｒ_１〜Ａｒ_２４が、置換あるいは無置換のベンゼン環３個以上が縮合した縮合多環芳香族基であることが好ましい。
【００４０】
本発明の有機発光素子は、一般式［Ｉ］〜一般式［ＶＩＩ］のＡｒ_１〜Ａｒ_２４が、下記一般式［ＶＩＩＩ］で示される縮合多環芳香族基であることが好ましい。
【００４１】
一般式［ＶＩＩＩ］
【外２８】

【００４２】
（式中、Ｒ_１９は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。）
本発明の有機発光素子は、一般式［Ｉ］〜一般式［ＶＩＩ］のＡｒ_１〜Ａｒ_２４が、下記一般式［ＩＸ］で示される縮合多環芳香族基であることが好ましい。
【００４３】
一般式［ＩＸ］
【外２９】

【００４４】
（式中、Ｒ_２０は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。）
本発明の有機発光素子は、一般式［Ｉ］〜一般式［ＶＩＩ］のＡｒ_１〜Ａｒ_２４が、下記一般式［Ｘ］で示される縮合多環芳香族基であることが好ましい。
【００４５】
一般式［Ｘ］
【外３０】

【００４６】
（式中、Ｒ_２１は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。）
本発明の有機発光素子は、一般式［Ｉ］〜一般式［ＶＩＩ］のＡｒ_１〜Ａｒ_２４が、下記一般式［ＸＩ］で示される縮合多環芳香族基であることが好ましい。
【００４７】
一般式［ＸＩ］
【外３１】

【００４８】
（式中、Ｒ_２２は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。）
本発明の有機発光素子は、一般式［Ｉ］〜一般式［ＶＩＩ］のＡｒ_１〜Ａｒ_２４が、下記一般式［ＸＩＩ］で示される縮合多環芳香族基であることが好ましい。
【００４９】
一般式［ＸＩＩ］
【外３２】

【００５０】
（式中、Ｒ_２３は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。）
本発明の有機発光素子は、一般式［Ｉ］〜一般式［ＶＩＩ］のＡｒ_１〜Ａｒ_２４が、下記一般式［ＸＩＩＩ］で示される縮合多環芳香族基であることが好ましい。
【００５１】
一般式［ＸＩＩＩ］
【外３３】

【００５２】
（式中、Ｒ_２４、Ｒ_２５、Ｒ_２６は、水素原子、アルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基またはシアノ基を表わす。）
本発明の有機発光素子は、有機化合物からなる層のうち少なくとも電子輸送層または発光層が、一般式［Ｉ］、一般式［ＩＩ］、一般式［ＩＩＩ］、一般式［ＩＶ］、一般式［Ｖ］、一般式［ＶＩ］および一般式［ＶＩＩ］で示される縮合多環化合物の少なくとも一種を含有することが好ましい。
上記一般式［Ｉ］〜一般式［ＶＩＩ］における置換基の具体例を以下に示す。
【００５３】
アルキル基としては、メチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｔｅｒ−ブチル基、オクチル基などが挙げられる。
【００５４】
アラルキル基としては、ベンジル基、フェネチル基などが挙げられる。
【００５５】
アリール基としては、フェニル基、ビフェニル基、ターフェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基、テトラセニル基、ペンタセニル基、フルオレニル基などが挙げられる。
【００５６】
複素環基としては、チエニル基、ピロリル基、ピリジル基、キノリル基、カルバゾリル基、オキサゾリル基、オキサジアゾリル基、チアゾリル基、チアジアゾリル基、ターチエニル基、ターピロリル基などが挙げられる。
【００５７】
置換アミノ基としては、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基などが挙げられる。
【００５８】
上記置換基が有してもよい置換基としては、メチル基、エチル基、プロピル基などのアルキル基、ベンジル基、フェネチル基などのアラルキル基、フェニル基、ナフチル基、アンスリル基、フェナンスリル基、ピレニル基、テトラセニル基、ペンタセニル基、フルオレニル基などのアリール基、チエニル基、ピロリル基、ピリジル基などの複素環基、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基などのアミノ基、メトキシル基、エトキシル基、プロポキシル基、フェノキシル基などのアルコキシル基、シアノ基、ニトロ基などが挙げられる。
【００５９】
次に、本発明の縮合多環化合物の代表例を以下に挙げるが、本発明はこれらに限定されるものではない。
【００６０】
［本実施形態の化合物例］
一般式［Ｉ］
【外３４】

【００６１】
【外３５】

【００６２】
【外３６】

【００６３】
一般式［ＩＩ］
【外３７】

【００６４】
【外３８】

【００６５】
【外３９】

【００６６】
【外４０】

【００６７】
一般式［ＩＩＩ］
【外４１】

【００６８】
【外４２】

【００６９】
【外４３】

【００７０】
一般式［ＩＶ］
【外４４】

【００７１】
【外４５】

【００７２】
一般式［Ｖ］
【外４６】

【００７３】
【外４７】

【００７４】
一般式［ＶＩ］
【外４８】

【００７５】
【外４９】

【００７６】
一般式［ＶＩＩ］
【外５０】

【００７７】
【外５１】

【００７８】
本発明の縮合多環化合物は、一般的に知られている方法で合成でき、例えば、パラジウム触媒を用いた用いたｓｕｚｕｋｉ ｃｏｕｐｌｉｎｇ法（例えばＣｈｅｍ．Ｒｅｖ．１９９５，９５，２４５７−２４８３）、ニッケル触媒を用いたＹａｍａｍｏｔｏ法（例えばＢｕｌｌ．Ｃｈｅｍ．Ｓｏｃ．Ｊｐｎ．５１，２０９１，１９７８）、アリールスズ化合物を用いて合成する方法（例えばＪ．Ｏｒｇ．Ｃｈｅｍ．，５２，４２９６，１９８７）などの合成法で得ることができる。
【００７９】
本発明の一般式［Ｉ］〜一般式［ＶＩＩ］で示される縮合多環化合物は、従来の化合物に比べ電子輸送性、発光性および耐久性の優れた化合物であり、有機発光素子の有機化合物を含む層、特に、電子輸送層および発光層として有用であり、また真空蒸着法や溶液塗布法などによって形成した層は結晶化などが起こりにくく経時安定性に優れている。
【００８０】
次に、本発明の有機発光素子について詳細に説明する。
【００８１】
本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に狭持された一または複数の有機化合物を含む層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が一般式［Ｉ］〜一般式［ＶＩＩ］で示される縮合多環化合物の少なくとも一種を含有することを特徴とする。
【００８２】
本発明の有機発光素子は、有機化合物を含む層のうち少なくとも電子輸送層または発光層が、前記縮合多環化合物の少なくとも一種を含有することが好ましい。
【００８３】
本発明の有機発光素子においては、上記一般式［Ｉ］〜一般式［ＶＩＩ］で示される縮合多環化合物を真空蒸着法や溶液塗布法により陽極及び陰極の間に形成する。その有機層の厚みは１０μｍより薄く、好ましくは０．５μｍ以下、より好ましくは０．０１〜０．５μｍの厚みに薄膜化することが好ましい。
【００８４】
図１〜図６に本発明の有機発光素子の好ましい例を示す。
【００８５】
図１は本発明の有機発光素子の一例を示す断面図である。図１は基板１上に陽極２、発光層３及び陰極４を順次設けた構成のものである。ここで使用する発光素子はそれ自体でホール輸送能、エレクトロン輸送能及び発光性の性能を単一で有している場合や、それぞれの特性を有する化合物を混ぜて使う場合に有用である。
【００８６】
図２は本発明の有機発光素子における他の例を示す断面図である。図２は基板１上に陽極２、ホール輸送層５、電子輸送層６及び陰極４を順次設けた構成のものである。この場合は発光物質はホール輸送性かあるいは電子輸送性のいづれかあるいは両方の機能を有している材料をそれぞれの層に用い、発光性の無い単なるホール輸送物質あるいは電子輸送物質と組み合わせて用いる場合に有用である。また、この場合発光層３はホール輸送層５あるいは電子輸送層６のいづれかから成る。
【００８７】
図３は本発明の有機発光素子における他の例を示す断面図である。図３は基板１上に陽極２、ホール輸送層５、発光層３，電子輸送層６及び陰極４を順次設けた構成のものである。これはキャリヤ輸送と発光の機能を分離したものであり、ホール輸送性、電子輸送性、発光性の各特性を有した化合物と適時組み合わせて用いられ極めて材料選択の自由度が増すとともに、発光波長を異にする種々の化合物が使用できるため、発光色相の多様化が可能になる。
【００８８】
さらに、中央の発光層に各キャリヤあるいは励起子を有効に閉じこめて発光効率の向上を図ることも可能になる。
【００８９】
図４は本発明の有機発光素子における他の例を示す断面図である。図４は図３に対してホール注入層７を陽極側に挿入した構成であり、陽極とホール輸送層の密着性改善あるいはホールの注入性改善に効果があり、低電圧化に効果的である。
【００９０】
図５および図６は本発明の有機発光素子における他の例を示す断面図である。図５および図６は、図３および図４に対して ホールあるいは励起子（エキシトン）を陰極側に抜けることを阻害する層（ホールブロッキング層８）を、発光層、電子輸送層間に挿入した構成である。イオン化ポテンシャルの非常に高い化合物をホールブロッキング層８として用いる事により、発光効率の向上に効果的な構成である。
【００９１】
ただし、図１〜図６はあくまでごく基本的な素子構成であり、本発明の化合物を用いた有機発光素子の構成はこれらに限定されるものではない。例えば、電極と有機層界面に絶縁性層を設ける、接着層あるいは干渉層を設ける。ホール輸送層がイオン化ポテンシャルの異なる２層から構成される。など多様な層構成をとることができる。
【００９２】
本発明に用いられる一般式［Ｉ］〜一般式［ＶＩＩ］で示される縮合多環化合物は、従来の化合物に比べ電子輸送性、発光性および耐久性の優れた化合物であり、図１〜図６のいずれの形態でも使用することができる。
【００９３】
特に、本発明の縮合多環化合物を用いた有機層は、電子輸送層および発光層として有用であり、また真空蒸着法や溶液塗布法などによって形成した層は結晶化などが起こりにくく経時安定性に優れている。
【００９４】
本発明は、電子輸送層および発光層の構成成分として一般式［Ｉ］〜一般式［ＶＩＩ］で示される縮合多環化合物を用いるものであるが、これまで知られているホール輸送性化合物、発光性化合物あるいは電子輸送性化合物などを必要に応じて一緒に使用することもできる。
【００９５】
以下にこれらの化合物例を挙げる。
【００９６】
ホール輸送性化合物
【外５２】

【００９７】
電子輸送性発光材料
【外５３】

【００９８】
発光材料
【外５４】

【００９９】
発光層マトリックス材料および電子輸送材料
【外５５】

【０１００】
ポリマー系ホール輸送性材料
【外５６】

【０１０１】
ポリマー系発光材料および電荷輸送性材料
【外５７】

【０１０２】
本発明の有機発光素子において、一般式［Ｉ］〜一般式［ＶＩＩ］で示される縮合多環化合物を含有する層および他の有機化合物を含有する層は、一般には真空蒸着法あるいは、適当な溶媒に溶解させて塗布法により薄膜を形成する。特に塗布法で成膜する場合は、適当な結着樹脂と組み合わせて膜を形成することもできる。
【０１０３】
上記結着樹脂としては広範囲な結着性樹脂より選択でき、たとえばポリビニルカルバゾール樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ポリアリレート樹脂、ポリスチレン樹脂、アクリル樹脂、メタクリル樹脂、ブチラール樹脂、ポリビニルアセタール樹脂、ジアリルフタレート樹脂、フェノール樹脂、エポキシ樹脂、シリコーン樹脂、ポリスルホン樹脂、尿素樹脂等が挙げられるが、これらに限定されるものではない。また、これらは単独または共重合体ポリマーとして１種または２種以上混合してもよい。
【０１０４】
陽極材料としては仕事関数がなるべく大きなものがよく、例えば、金、白金、ニッケル、パラジウム、コバルト、セレン、バナジウム等の金属単体あるいはこれらの合金、酸化錫、酸化亜鉛、酸化錫インジウム（ＩＴＯ），酸化亜鉛インジウム等の金属酸化物が使用できる。また、ポリアニリン、ポリピロール、ポリチオフェン、ポリフェニレンスルフィド等の導電性ポリマーも使用できる。これらの電極物質は単独で用いてもよく、複数併用することもできる。
【０１０５】
一方、陰極材料としては仕事関数の小さなものがよく、リチウム、ナトリウム、カリウム、カルシウム、マグネシウム、アルミニウム、インジウム、銀、鉛、錫、クロム等の金属単体あるいは複数の合金として用いることができる。酸化錫インジウム（ＩＴＯ）等の金属酸化の利用も可能である。また、陰極は一層構成でもよく、多層構成をとることもできる。
【０１０６】
本発明で用いる基板としては、特に限定するものではないが、金属製基板、セラミックス製基板等の不透明性基板、ガラス、石英、プラスチックシート等の透明性基板が用いられる。また、基板にカラーフィルター膜、蛍光色変換フィルター膜、誘電体反射膜などを用いて発色光をコントロールする事も可能である。
【０１０７】
なお、作成した素子に対して、酸素や水分等との接触を防止する目的で保護層あるいは封止層を設けることもできる。保護層としては、ダイヤモンド薄膜、金属酸化物、金属窒化物等の無機材料膜、フッソ樹脂、ポリパラキシレン、ポリエチレン、シリコーン樹脂、ポリスチレン樹脂等の高分子膜さらには、光硬化性樹脂等が挙げられる。また、ガラス、気体不透過性フィルム、金属などをカバーし、適当な封止樹脂により素子自体をパッケージングすることもできる。
【０１０８】
【実施例】
以下、実施例により本発明をさらに具体的に説明していくが、本発明はこれらに限定されるものではない。
【０１０９】
［実施例１］
図２に示す構造の素子を作成した。
【０１１０】
基板１としてのガラス基板上に、陽極２としての酸化錫インジウム（ＩＴＯ）をスパッタ法にて１２０ｎｍの膜厚で成膜したものを透明導電性支持基板として用いた。これをアセトン、イソプロピルアルコール（ＩＰＡ）で順次超音波洗浄し、次いでＩＰＡで煮沸洗浄後乾燥した。さらに、ＵＶ／オゾン洗浄したものを透明導電性支持基板として使用した。
【０１１１】
透明導電性支持基板上に下記構造式で示される化合物のクロロホルム溶液をスピンコート法により３０ｎｍの膜厚で成膜しホール輸送層５を形成した。
【外５８】

【０１１２】
さらに例示化合物Ｎｏ．１１で示される縮合多環化合物を真空蒸着法により５０ｎｍの膜厚で成膜し電子輸送層６を形成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１１３】
次に、陰極４として、アルミニウムとリチウム（リチウム濃度１原子％）からなる蒸着材料を用いて、上記有機層の上に、真空蒸着法により厚さ１５０ｎｍの金属層膜を形成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は１．０〜１．２ｎｍ／ｓｅｃの条件で成膜した。
【０１１４】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、１０Ｖの直流電圧を印加すると９．３ｍＡ／ｃｍ^２の電流密度で電流が素子に流れ、１４００ｃｄ／ｍ^２の輝度で青色の発光が観測された。
【０１１５】
さらに、窒素雰囲気下で電流密度を７．０ｍＡ／ｃｍ^２に保ち１００時間電圧を印加したところ、初期輝度１１００ｃｄ／ｍ^２から１００時間後１０００ｃｄ／ｍ^２と輝度劣化は小さかった。
【０１１６】
［実施例２〜１０］
例示化合物Ｎｏ．１１に代えて、例示化合物Ｎｏ．１，１３，２２，２６，２７，３２，３９，４２，４４を用いた他は実施例１と同様に素子を作成し、同様な評価を行った。
【０１１７】
結果を表−１に示す。
【０１１８】
［比較例１〜８］
例示化合物Ｎｏ．１１に代えて、下記構造式で示される化合物を用いた他は実施例１と同様に素子を作成し、同様な評価を行った。
【０１１９】
結果を表−１に示す。
【０１２０】
比較化合物Ｎｏ．１
【外５９】

【０１２１】
比較化合物Ｎｏ．２
【外６０】

【０１２２】
比較化合物Ｎｏ．３
【外６１】

【０１２３】
比較化合物Ｎｏ．４
【外６２】

【０１２４】
比較化合物Ｎｏ．５
【外６３】

【０１２５】
比較化合物Ｎｏ．６
【外６４】

【０１２６】
比較化合物Ｎｏ．７
【外６５】

【０１２７】
比較化合物Ｎｏ．８
【外６６】

【０１２８】
【表１】

【０１２９】
［実施例１１］
図３に示す構造の素子を作成した。
【０１３０】
実施例１と同様に、透明導電性支持基板上にホール輸送層５を形成した。
【０１３１】
さらに例示化合物Ｎｏ．１１で示される縮合多環化合物を真空蒸着法により２０ｎｍの膜厚で成膜し発光層３を形成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１３２】
さらにアルミニウムトリスキノリノールを真空蒸着法により４０ｎｍの膜厚で成膜し電子輸送層６を形成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１３３】
次に、陰極４として、アルミニウムとリチウム（リチウム濃度１原子％）からなる蒸着材料を用いて、上記有機層の上に、真空蒸着法により厚さ１５０ｎｍの金属層膜を形成し、図３に示す構造の素子を作成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は１．０〜１．２ｎｍ／ｓｅｃの条件で成膜した。
【０１３４】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、８Ｖの直流電圧を印加すると８．４ｍＡ／ｃｍ^２の電流密度で電流が素子に流れ、８５００ｃｄ／ｍ^２の輝度で青色の発光が観測された。
【０１３５】
さらに、窒素雰囲気下で電流密度を７．０ｍＡ／ｃｍ^２に保ち１００時間電圧を印加したところ、初期輝度７６００ｃｄ／ｍ^２から１００時間後６４００ｃｄ／ｍ^２と輝度劣化は小さかった。
【０１３６】
［実施例１２〜２０］
例示化合物Ｎｏ．１１に代えて、例示化合物Ｎｏ．６，９，１５，２０，２４，３５，３７，４３，４６を用いた他は実施例１１と同様に素子を作成し、同様な評価を行った。
【０１３７】
結果を表−２に示す。
【０１３８】
［比較例９〜１６］
例示化合物Ｎｏ．１１に代えて、比較化合物Ｎｏ．１、２、３、４，５，６，７，８を用いた他は実施例１１と同様に素子を作成し、同様な評価を行った。
【０１３９】
結果を表−２に示す。
【０１４０】
【表２】

【０１４１】
［実施例２１］
図３に示す構造の素子を作成した。
【０１４２】
実施例１と同様な透明導電性支持基板上に、下記構造式で示される化合物のクロロホルム溶液をスピンコート法により２０ｎｍの膜厚で成膜しホール輸送層５を形成した。
【外６７】

【０１４３】
さらに下記構造式で示される化合物および例示化合物Ｎｏ．１１で示される縮合多環化合物（重量比１：５０）を真空蒸着法により２０ｎｍの膜厚で成膜し発光層３を形成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【外６８】

【０１４４】
さらにアルミニウムトリスキノリノールを真空蒸着法により４０ｎｍの膜厚で成膜し電子輸送層６を形成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１４５】
次に、陰極４として、アルミニウムとリチウム（リチウム濃度１原子％）からなる蒸着材料を用いて、上記有機層の上に、真空蒸着法により厚さ１５０ｎｍの金属層膜を形成し、図３に示す構造の素子を作成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は１．０〜１．２ｎｍ／ｓｅｃの条件で成膜した。
【０１４６】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、８Ｖの直流電圧を印加すると８．８ｍＡ／ｃｍ^２の電流密度で電流が素子に流れ、８２０００ｃｄ／ｍ^２の輝度で青色の発光が観測された。
【０１４７】
さらに、窒素雰囲気下で電流密度を５．０ｍＡ／ｃｍ^２に保ち１００時間電圧を印加したところ、初期輝度３９０００ｃｄ／ｍ^２から１００時間後３３０００ｃｄ／ｍ^２と輝度劣化は小さかった。
【０１４８】
［実施例２２〜３０］
例示化合物Ｎｏ．１１に代えて、例示化合物Ｎｏ．２，１０，１４，２１，２５，３０，３６，４０，４７を用いた他は実施例２１と同様に素子を作成し、同様な評価を行った。
【０１４９】
結果を表−３に示す。
【０１５０】
［比較例１７〜２４］
例示化合物Ｎｏ．１１に代えて、比較化合物Ｎｏ．１、２、３、４，５，６，７，８を用いた他は実施例２１と同様に素子を作成し、同様な評価を行った。
結果を表−３に示す。
【０１５１】
【表３】

【０１５２】
［実施例３１］
図５に示す構造の素子を作成した。
【０１５３】
実施例２１と同様に、透明導電性支持基板上にホール輸送層５を形成した。さらにルブレンおよびアルミニウムトリスキノリノール（重量比１：２０）を真空蒸着法により２０ｎｍの膜厚で成膜し発光層３を形成した後、例示化合物Ｎｏ．１１で示される縮合多環化合物を真空蒸着法により１０ｎｍの膜厚で成膜しホール／エキシトンブロッキング層８を形成した。さらにアルミニウムトリスキノリノールを真空蒸着法により４０ｎｍの膜厚で成膜し電子輸送層６を形成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１５４】
次に、陰極４として、アルミニウムとリチウム（リチウム濃度１原子％）からなる蒸着材料を用いて、上記有機層の上に、真空蒸着法により厚さ１５０ｎｍの金属層膜を形成し、図５に示す構造の素子を作成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は１．０〜１．２ｎｍ／ｓｅｃの条件で成膜した。
【０１５５】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、１０Ｖの直流電圧を印加すると９．１ｍＡ／ｃｍ^２の電流密度で電流が素子に流れ、８１０００ｃｄ／ｍ^２の輝度で黄緑色の発光が観測された。
【０１５６】
さらに、窒素雰囲気下で電流密度を７．０ｍＡ／ｃｍ^２に保ち１００時間電圧を印加したところ、初期輝度５１０００ｃｄ／ｍ^２から１００時間後３９０００ｃｄ／ｍ^２と輝度劣化は小さかった。
【０１５７】
［実施例３２〜４０］
例示化合物Ｎｏ．１１に代えて、例示化合物Ｎｏ．３，７，１８，１９，２８，３１，３８，４１，４５を用いた他は実施例３１と同様に素子を作成し、同様な評価を行った。
【０１５８】
結果を表−４に示す。
【０１５９】
［比較例２５〜３２］
例示化合物Ｎｏ．１１に代えて、比較化合物Ｎｏ．１、２、３、４，５，６，７，８を用いた他は実施例３１と同様に素子を作成し、同様な評価を行った。
結果を表−４に示す。
【０１６０】
【表４】

【０１６１】
［実施例４１］
図３に示す構造の素子を作成した。
【０１６２】
実施例１と同様な透明導電性支持基板上に、下記構造式で示される化合物のクロロホルム溶液をスピンコート法により２０ｎｍの膜厚で成膜しホール輸送層５を形成した。
【外６９】

【０１６３】
さらに下記構造式で示される化合物および例示化合物Ｎｏ．１１で示される縮合多環化合物（重量比１：５０）を真空蒸着法により２０ｎｍの膜厚で成膜し発光層３を形成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【外７０】

【０１６４】
さらにアルミニウムトリスキノリノールを真空蒸着法により４０ｎｍの膜厚で成膜し電子輸送層６を形成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１６５】
次に、陰極４として、アルミニウムとリチウム（リチウム濃度１原子％）からなる蒸着材料を用いて、上記有機層の上に、真空蒸着法により厚さ１５０ｎｍの金属層膜を形成し、図３に示す構造の素子を作成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は１．０〜１．２ｎｍ／ｓｅｃの条件で成膜した。
【０１６６】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、８Ｖの直流電圧を印加すると７．７ｍＡ／ｃｍ^２の電流密度で電流が素子に流れ、１２０００ｃｄ／ｍ^２の輝度で緑色の発光が観測された。
【０１６７】
さらに、窒素雰囲気下で電流密度を５．０ｍＡ／ｃｍ^２に保ち１００時間電圧を印加したところ、初期輝度８６００ｃｄ／ｍ^２から１００時間後７８００ｃｄ／ｍ^２と輝度劣化は小さかった。
【０１６８】
［実施例４２〜５０］
例示化合物Ｎｏ．１１に代えて、例示化合物Ｎｏ．４，８，１２，１６，２３，２９，３４，４３，４４を用いた他は実施例４１と同様に素子を作成し、同様な評価を行った。
【０１６９】
結果を表−５に示す。
【０１７０】
［比較例３３〜４０］
例示化合物Ｎｏ．１１に代えて、比較化合物Ｎｏ．１、２、３、４，５，６、７，８を用いた他は実施例４１と同様に素子を作成し、同様な評価を行った。
結果を表−５に示す。
【０１７１】
【表５】

【０１７２】
［実施例５１］
図１に示す構造の素子を作成した。
【０１７３】
実施例１と同様な透明導電性支持基板上に、例示化合物Ｎｏ．１１で示される縮合多環化合物を０．０５０ｇおよびポリ−Ｎ−ビニルカルバゾール（重量平均分子量＝６３、０００）１．００ｇをクロロホルム８０ｍｌに溶解した溶液をスピンコート法（回転数＝２０００ｒｐｍ）により１２０ｎｍの膜厚に成膜し有機層（発光層３）を形成した。
【０１７４】
次に、陰極４として、アルミニウムとリチウム（リチウム濃度１原子％）からなる蒸着材料を用いて、上記有機層の上に、真空蒸着法により厚さ１５０ｎｍの金属層膜を形成し、図５に示す構造の素子を作成した。蒸着時の真空度は１．０×１０^−４Ｐａ、成膜速度は１．０〜１．２ｎｍ／ｓｅｃの条件で成膜した。
【０１７５】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、１０Ｖの直流電圧を印加すると７．５ｍＡ／ｃｍ^２の電流密度で電流が素子に流れ、１４００ｃｄ／ｍ^２の輝度で青色の発光が観測された。
【０１７６】
さらに、窒素雰囲気下で電流密度を５．０ｍＡ／ｃｍ^２に保ち１００時間電圧を印加したところ、初期輝度９２０ｃｄ／ｍ^２から１００時間後８７０ｃｄ／ｍ^２と輝度劣化は小さかった。
【０１７７】
［実施例５２〜５５］
例示化合物Ｎｏ．１１に代えて、例示化合物Ｎｏ．５，１７，３３，４７を用いた他は実施例５１と同様に素子を作成し、同様な評価を行った。
結果を表−６に示す。
【０１７８】
［比較例４１〜４８］
例示化合物Ｎｏ．１１に代えて、比較化合物Ｎｏ．１、２、３、４，５，６，７，８を用いた他は実施例５１と同様に素子を作成し、同様な評価を行った。
結果を表−６に示す。
【０１７９】
【表６】

【０１８０】
【発明の効果】
以上説明のように、一般式［Ｉ］〜一般式［ＶＩＩ］で示される縮合多環化合物を用いた有機発光素子は、低い印加電圧で高輝度な発光が得られ、耐久性にも優れている。特に本発明の縮合多環化合物を含有する有機層は、電子輸送層として優れ、かつ発光層としても優れている。
【０１８１】
さらに、素子の作成も真空蒸着あるいはキャステイング法等を用いて作成可能であり、比較的安価で大面積の素子を容易に作成できる。
【図面の簡単な説明】
【図１】本発明における有機発光素子の一例を示す断面図である。
【図２】本発明における有機発光素子の他の例を示す断面図である。
【図３】本発明における有機発光素子の他の例を示す断面図である。
【図４】本発明における有機発光素子の他の例を示す断面図である。
【図５】本発明における有機発光素子の他の例を示す断面図である。
【図６】本発明における有機発光素子の他の例を示す断面図である。
【符号の説明】
１ 基板
２ 陽極
３ 発光層
４ 陰極
５ ホール輸送層
６ 電子輸送層
７ ホール注入層
８ ホール／エキシトンブロッキング層[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel organic compound and an organic light-emitting device using the same.
[0002]
[Prior art]
An organic light-emitting element generates an exciton of a fluorescent compound by sandwiching a thin film containing a fluorescent organic compound between an anode and a cathode and injecting electrons and holes from each electrode. It is an element that utilizes light emitted when the child returns to the ground state.
[0003]
In 1987, Kodak Research (Appl. Phys. Lett. 51, 913 (1987)) used ITO for the anode and magnesium-silver alloy for the cathode, and used an aluminum quinolinol complex as the electron transport material and light-emitting material. A functionally separated two-layer device using a triphenylamine derivative as a material, and 1000 cd / m at an applied voltage of about 10 V²A degree of luminescence has been reported. Related patents include US Pat. No. 4,539,507, US Pat. No. 4,720,432, US Pat. No. 4,885,211 and the like.
[0004]
In addition, by changing the type of the fluorescent organic compound, light emission from ultraviolet to infrared is possible, and recently, various compounds have been actively researched. For example, US Pat. No. 5,151,629, US Pat. No. 5,409,783, US Pat. No. 5,382,477, JP-A-2-247278, JP-A-3-255190, JP-A-5-202356. No. 9, JP-A-9-202878, JP-A-9-227576, and the like.
[0005]
In addition to organic light-emitting elements using low molecular materials as described above, organic light-emitting elements using conjugated polymers have been reported by a group of Cambridge University (Nature, 347, 539 (1990)). Yes. In this report, light emission is confirmed in a single layer by forming a film of polyphenylene vinylene (PPV) in a coating system.
Related patents for organic light emitting devices using conjugated polymers include US Pat. No. 5,247,190, US Pat. No. 5,514,878, US Pat. No. 5,672,678, and Japanese Patent Laid-Open No. 4-145192. JP, 5-247460, A, etc. are mentioned.
[0006]
As described above, recent advances in organic light-emitting devices are remarkable, and their features are high brightness, variety of emission wavelengths, high-speed response, low profile, and light-emitting devices with low applied voltage. Suggests the possibility to.
[0007]
However, under the present circumstances, light output with higher brightness or higher conversion efficiency is required. In addition, there are still many problems in terms of durability, such as changes over time due to long-term use and deterioration due to atmospheric gas containing oxygen or moisture. Furthermore, it is necessary to emit blue, green, and red light with good color purity when considering application to a full color display or the like, but these problems are still not sufficient.
[0008]
Many aromatic compounds and condensed polycyclic aromatic compounds have been studied as fluorescent organic compounds used in an electron transport layer, a light emitting layer, and the like. For example, JP-A-4-68076, JP-A-5-32966, JP-A-6-228552, JP-A-6-240244, JP-A-7-109454, JP-A-8-311442, JP-A-9-241629, JP-A-2000-26334, JP-A-2000-268964, and the like can be mentioned, but those which are sufficiently satisfactory in light emission luminance and durability have not been obtained.
[0009]
[Problems to be solved by the invention]
An object of the present invention is to provide an organic light emitting device using a specific condensed polycyclic compound and having an extremely high efficiency and high luminance light output. Another object of the present invention is to provide an extremely durable organic light emitting device. It is another object of the present invention to provide an organic light emitting device that is easy to manufacture and can be produced at a relatively low cost.
[0010]
[Means for Solving the Problems]
  Therefore, the present invention
  In an organic light-emitting element having at least a layer composed of an anode and a cathode and a layer composed of one or more organic compounds sandwiched between the pair of electrodes, at least one layer containing the organic compound is belowIn the structural formulaFused polycyclic compounds shownThingsProvided is an organic light-emitting device containing the organic light-emitting device.
[0011]
[Outside 14]

[0012]
  MaThe present invention
  In an organic light-emitting device having at least one layer composed of an anode and a cathode and one or more organic compound layers sandwiched between the pair of electrodes, at least one layer containing the organic compound has the following general formula [ An organic light-emitting device comprising at least one of the condensed polycyclic compounds represented by the formula II] is provided.
[0013]
Formula [II]
[Outside 15]

[0014]
(Wherein R₅,R ₆ Are bothHydrogen fieldIt is a child. R ₇ Is a hydrogen atom or a pyridinyl group.
Ar₃,Ar ₄ Are all fluoranthenyl groups, and any of the fluoranthenyl groups is bonded to the benzene ring represented by the general formula [II] at the 8-position..
Ar ₅ Is,The pyrenyl group is any one of a fluoranthenyl group, a phenanthrenyl group, a tetracenyl group, and a perylenyl group bonded to the benzene ring represented by the general formula [II] at the 8-position.)
  The present invention also provides
  In an organic light-emitting device having at least one layer composed of an anode and a cathode and one or more organic compound layers sandwiched between the pair of electrodes, at least one layer containing the organic compound has the following general formula [ The organic light-emitting device is characterized by containing at least one kind of the condensed polycyclic compound represented by [III].
[0015]
Formula [III]
[Outside 16]

[0016]
  (Wherein R₈And R₉ Are both waterSourceIt is a child.
Ar ₆ , Ar ₇ Are all fluoranthenyl groups, and any of the fluoranthenyl groups is bonded to the benzene ring represented by the general formula [III] at the 8-position..The fluoranthenyl group may have a phenyl group.
Ar ₈ andAr ₉ Are independently selected from an anthracenyl group, a fluoranthenyl group, a pentacenyl group, and a naphthyl group that are bonded to the benzene ring represented by the general formula [III] at the 8-position. The anthracenyl group and the naphthyl group may have an alkyl group.)
  The present invention also provides
  In an organic light-emitting element having at least a layer composed of an anode and a cathode and a layer composed of one or more organic compounds sandwiched between the pair of electrodes, at least one layer containing the organic compound is belowIn the structural formulaFused polycyclic compounds shownThingsProvided is an organic light-emitting device containing the organic light-emitting device.
[0017]
[Outside 15]

[0018]
  MaThe present invention
  In an organic light-emitting element having at least a layer composed of an anode and a cathode and a layer composed of one or more organic compounds sandwiched between the pair of electrodes, at least one layer containing the organic compound is belowIn the structural formulaFused polycyclic compounds shownThingsProvided is an organic light-emitting device containing the organic light-emitting device.
[0019]
[Outside 16]

[0020]
  MaThe present invention
  In an organic light-emitting element having at least a layer composed of an anode and a cathode and a layer composed of one or more organic compounds sandwiched between the pair of electrodes, at least one layer containing the organic compound is belowIn the structural formulaIndicatedAny reductionPolycyclic compoundThingsProvided is an organic light-emitting device containing the organic light-emitting device.
[0021]
[Outside 17]

[Outside 18]

[0022]
  MaThe present invention
  In an organic light-emitting element having at least a layer composed of an anode and a cathode and a layer composed of one or more organic compounds sandwiched between the pair of electrodes, at least one layer containing the organic compound is belowIn the structural formulaIndicatedAny reductionPolycyclic compoundThingsProvided is an organic light-emitting device containing the organic light-emitting device.
[0023]
[Outside 19]

[Outside 20]

[Outside 21]

[Outside 22]

[0025]
DETAILED DESCRIPTION OF THE INVENTION
The organic light emitting device of the present invention is a layer containing the organic compound in an organic light emitting device having at least a pair of electrodes composed of an anode and a cathode, and a layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes. At least one layer contains at least one condensed polycyclic compound represented by the following general formula [I].
[0026]
Formula [I]
[Outside 21]

[0027]
(Wherein R₁, R₂, R₃And R₄Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group or a cyano group. R₁, R₂, R₃And R₄May be the same or different. Ar₁And Ar₂Represents a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted condensed polycyclic heterocyclic group, Ar₁And Ar₂At least one of represents a fluoranthenyl group. Ar₁And Ar₂May be the same or different. )
The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a pair of electrodes composed of an anode and a cathode and a layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes. At least one layer contains at least one condensed polycyclic compound represented by the following general formula [II].
[0028]
Formula [II]
[Outside 22]

[0029]
(Wherein R₅, R₆And R₇Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group or a cyano group. R₅, R₆And R₇May be the same or different. Ar₃, Ar₄And Ar₅Represents a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted condensed polycyclic heterocyclic group, Ar₃, Ar₄And Ar₅At least one of represents a substituted or unsubstituted fluoranthenyl group. Ar₃, Ar₄And Ar₅May be the same or different. )
The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a pair of electrodes composed of an anode and a cathode and a layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes. At least one of the layers contains at least one condensed polycyclic compound represented by the following general formula [III].
[0030]
Formula [III]
[Outside 23]

[0031]
(Wherein R₈And R₉Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group or a cyano group. R₈And R₉May be the same or different. Ar₆, Ar₇, Ar₈And Ar₉Represents a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted condensed polycyclic heterocyclic group, Ar₆, Ar₇, Ar₈And Ar₉At least one of represents a substituted or unsubstituted fluoranthenyl group. Ar₆, Ar₇, Ar₈And Ar₉May be the same or different. )
The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a pair of electrodes composed of an anode and a cathode and a layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes. At least one of the layers contains at least one condensed polycyclic compound represented by the following general formula [IV].
[0032]
Formula [IV]
[Outside 24]

[0033]
(Wherein R₁₀, R₁₁, R₁₂And R₁₃Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group or a cyano group. R₁₀, R₁₁, R₁₂And R₁₃May be the same or different. Ar₁₀And Ar₁₁Represents a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted condensed polycyclic heterocyclic group, Ar₁₀And Ar₁₁At least one of represents a substituted or unsubstituted fluoranthenyl group. Ar₁₀And Ar₁₁May be the same or different. )
The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a pair of electrodes composed of an anode and a cathode and a layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes. At least one layer contains at least one condensed polycyclic compound represented by the following general formula [V].
[0034]
General formula [V]
[Outside 25]

[0035]
(Wherein R₁₄, R₁₅And R₁₆Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group or a cyano group. R₁₄, R₁₅And R₁₆May be the same or different. Ar₁₂, Ar₁₃And Ar₁₄Represents a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted condensed polycyclic heterocyclic group, Ar₁₂, Ar₁₃And Ar₁₄At least one of represents a substituted or unsubstituted fluoranthenyl group. Ar₁₂, Ar₁₃And Ar₁₄May be the same or different. )
The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a pair of electrodes composed of an anode and a cathode and a layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes. At least one layer contains at least one condensed polycyclic compound represented by the following general formula [VI].
[0036]
Formula [VI]
[Outside 26]

[0037]
(Wherein R₁₇And R₁₈Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group or a cyano group. R₁₇And R₁₈May be the same or different. Ar₁₅, Ar₁₆, Ar₁₇And Ar₁₈Represents a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted condensed polycyclic heterocyclic group, Ar₁₅, Ar₁₆, Ar₁₇And Ar₁₈At least one of represents a substituted or unsubstituted fluoranthenyl group. Ar₁₅, Ar₁₆, Ar₁₇And Ar₁₈May be the same or different. )
The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a pair of electrodes composed of an anode and a cathode and a layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes. At least one of the layers is characterized by containing at least one condensed polycyclic compound represented by the following general formula [VII].
[0038]
Formula [VII]
[Outside 27]

[0039]
(Wherein Ar₁₉, Ar₂₀, Ar₂₁, Ar₂₂, Ar₂₃And Ar₂₄Represents a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted condensed polycyclic heterocyclic group, Ar₁₅, Ar₁₆, Ar₁₇And Ar₁₈At least one of represents a substituted or unsubstituted fluoranthenyl group. Ar₁₅, Ar₁₆, Ar₁₇And Ar₁₈They may be the same or different. )
The organic light-emitting device of the present invention has Ar of general formula [I] to general formula [VII].₁~ Ar₂₄However, it is preferably a condensed polycyclic aromatic group in which 3 or more substituted or unsubstituted benzene rings are condensed.
[0040]
The organic light-emitting device of the present invention has Ar of general formula [I] to general formula [VII].₁~ Ar₂₄Is preferably a condensed polycyclic aromatic group represented by the following general formula [VIII].
[0041]
Formula [VIII]
[Outside 28]

[0042]
(Wherein R₁₉Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, or a cyano group. )
The organic light-emitting device of the present invention has Ar of general formula [I] to general formula [VII].₁~ Ar₂₄Is preferably a condensed polycyclic aromatic group represented by the following general formula [IX].
[0043]
Formula [IX]
[Outside 29]

[0044]
(Wherein R₂₀Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, or a cyano group. )
The organic light-emitting device of the present invention has Ar of general formula [I] to general formula [VII].₁~ Ar₂₄Is preferably a condensed polycyclic aromatic group represented by the following general formula [X].
[0045]
Formula [X]
[Outside 30]

[0046]
(Wherein R₂₁Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, or a cyano group. )
The organic light-emitting device of the present invention has Ar of general formula [I] to general formula [VII].₁~ Ar₂₄Is preferably a condensed polycyclic aromatic group represented by the following general formula [XI].
[0047]
Formula [XI]
[Outside 31]

[0048]
(Wherein R₂₂Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, or a cyano group. )
The organic light-emitting device of the present invention has Ar of general formula [I] to general formula [VII].₁~ Ar₂₄Is preferably a condensed polycyclic aromatic group represented by the following general formula [XII].
[0049]
Formula [XII]
[Outside 32]

[0050]
(Wherein R₂₃Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, or a cyano group. )
The organic light-emitting device of the present invention has Ar of general formula [I] to general formula [VII].₁~ Ar₂₄Is preferably a condensed polycyclic aromatic group represented by the following general formula [XIII].
[0051]
Formula [XIII]
[Outside 33]

[0052]
(Wherein R₂₄, R₂₅, R₂₆Represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, or a cyano group. )
In the organic light-emitting device of the present invention, at least the electron transport layer or the light-emitting layer among the layers made of an organic compound has a general formula [I], a general formula [II], a general formula [III], a general formula [IV], or a general formula. It is preferable to contain at least one of the condensed polycyclic compounds represented by [V], general formula [VI] and general formula [VII].
Specific examples of the substituents in the above general formulas [I] to [VII] are shown below.
[0053]
Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a ter-butyl group, and an octyl group.
[0054]
Examples of the aralkyl group include a benzyl group and a phenethyl group.
[0055]
Examples of the aryl group include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, and a fluorenyl group.
[0056]
Examples of the heterocyclic group include thienyl group, pyrrolyl group, pyridyl group, quinolyl group, carbazolyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, tertenyl group, terpyrrolyl group and the like.
[0057]
Examples of the substituted amino group include a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, a ditolylamino group, and a dianisolylamino group.
[0058]
Examples of the substituent that the above substituent may have include alkyl groups such as methyl, ethyl, and propyl, aralkyl groups such as benzyl and phenethyl, phenyl, naphthyl, anthryl, phenanthryl, and pyrenyl. Group, tetracenyl group, pentacenyl group, aryl group such as fluorenyl group, heterocyclic group such as thienyl group, pyrrolyl group, pyridyl group, dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, dianiso group Examples include amino groups such as a rilamino group, methoxyl groups, ethoxyl groups, propoxyl groups, alkoxyl groups such as phenoxyl groups, cyano groups, and nitro groups.
[0059]
Next, typical examples of the condensed polycyclic compound of the present invention are listed below, but the present invention is not limited thereto.
[0060]
[Example of Compound of this Embodiment]
Formula [I]
[Outside 34]

[0061]
[Outside 35]

[0062]
[Outside 36]

[0063]
Formula [II]
[Outside 37]

[0064]
[Outside 38]

[0065]
[Outside 39]

[0066]
[Outside 40]

[0067]
Formula [III]
[Outside 41]

[0068]
[Outside 42]

[0069]
[Outside 43]

[0070]
Formula [IV]
[Outside 44]

[0071]
[Outside 45]

[0072]
General formula [V]
[Outside 46]

[0073]
[Outside 47]

[0074]
Formula [VI]
[Outside 48]

[0075]
[Outside 49]

[0076]
Formula [VII]
[Outside 50]

[0077]
[Outside 51]

[0078]
The condensed polycyclic compound of the present invention can be synthesized by a generally known method. For example, a Suzuki coupling method using a palladium catalyst (for example, Chem. Rev. 1995, 95, 2457-2483), nickel catalyst Yamamoto method (for example, Bull. Chem. Soc. Jpn. 51, 2091, 1978) and a synthesis method using an aryl tin compound (for example, J. Org. Chem., 52, 4296, 1987). Obtainable.
[0079]
The condensed polycyclic compound represented by the general formula [I] to the general formula [VII] of the present invention is a compound excellent in electron transporting property, light emitting property and durability as compared with conventional compounds, and is an organic compound of an organic light emitting device. In particular, a layer formed by a vacuum vapor deposition method, a solution coating method, or the like is less susceptible to crystallization and has excellent temporal stability.
[0080]
Next, the organic light emitting device of the present invention will be described in detail.
[0081]
The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a layer including a pair of electrodes composed of an anode and a cathode and one or more organic compounds sandwiched between the pair of electrodes. At least one of the layers contains at least one of the condensed polycyclic compounds represented by the general formulas [I] to [VII].
[0082]
In the organic light-emitting device of the present invention, it is preferable that at least the electron transport layer or the light-emitting layer in the layer containing an organic compound contains at least one of the condensed polycyclic compounds.
[0083]
In the organic light emitting device of the present invention, the condensed polycyclic compound represented by the general formula [I] to the general formula [VII] is formed between the anode and the cathode by a vacuum deposition method or a solution coating method. The thickness of the organic layer is less than 10 μm, preferably 0.5 μm or less, more preferably 0.01 to 0.5 μm.
[0084]
1 to 6 show preferred examples of the organic light emitting device of the present invention.
[0085]
FIG. 1 is a cross-sectional view showing an example of the organic light emitting device of the present invention. FIG. 1 shows a structure in which an anode 2, a light emitting layer 3 and a cathode 4 are sequentially provided on a substrate 1. The light-emitting element used here is useful when it has a single hole transport ability, electron transport ability, and light-emitting performance, or when a compound having each characteristic is mixed.
[0086]
FIG. 2 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 2 shows a configuration in which an anode 2, a hole transport layer 5, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. In this case, the luminescent material is either a hole transporting or electron transporting material, or a material having both functions is used for each layer, and it is used in combination with a mere hole transporting material or electron transporting material that does not emit light. Useful for. In this case, the light emitting layer 3 is composed of either the hole transport layer 5 or the electron transport layer 6.
[0087]
FIG. 3 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 3 shows a structure in which an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. This is a separation of carrier transport and light emission functions. It is used in combination with compounds having hole transport properties, electron transport properties, and light emission properties in a timely manner. Since various compounds having different values can be used, it is possible to diversify the emission hue.
[0088]
In addition, it is possible to effectively confine each carrier or exciton in the central light emitting layer to improve the light emission efficiency.
[0089]
FIG. 4 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 4 shows a configuration in which a hole injection layer 7 is inserted on the anode side with respect to FIG. 3, which is effective in improving the adhesion between the anode and the hole transport layer or improving the hole injection property, and effective in lowering the voltage. .
[0090]
5 and 6 are cross-sectional views showing other examples of the organic light-emitting device of the present invention. 5 and 6 show a structure in which a layer (hole blocking layer 8) that prevents holes or excitons (excitons) from passing to the cathode side is inserted between the light emitting layer and the electron transport layer, as compared with FIGS. It is. By using a compound having a very high ionization potential as the hole blocking layer 8, the structure is effective in improving the light emission efficiency.
[0091]
However, FIGS. 1 to 6 are very basic device configurations, and the configuration of the organic light-emitting device using the compound of the present invention is not limited thereto. For example, an adhesive layer or an interference layer is provided at the interface between the electrode and the organic layer. The hole transport layer is composed of two layers having different ionization potentials. Various layer configurations can be taken.
[0092]
The condensed polycyclic compound represented by the general formula [I] to general formula [VII] used in the present invention is a compound excellent in electron transport property, light emitting property and durability as compared with conventional compounds. Any form of 6 can be used.
[0093]
In particular, an organic layer using the condensed polycyclic compound of the present invention is useful as an electron transport layer and a light emitting layer, and a layer formed by a vacuum deposition method or a solution coating method is less likely to be crystallized and stable over time. Is excellent.
[0094]
In the present invention, the condensed polycyclic compound represented by the general formula [I] to the general formula [VII] is used as a constituent component of the electron transport layer and the light emitting layer. A luminescent compound, an electron transporting compound, or the like can be used together as necessary.
[0095]
Examples of these compounds are given below.
[0096]
Hole transport compound
[Outside 52]

[0097]
Electron transporting luminescent material
[Outside 53]

[0098]
Luminescent material
[Outside 54]

[0099]
Light emitting layer matrix material and electron transport material
[Outside 55]

[0100]
Polymer-based hole transport material
[Outside 56]

[0101]
Polymer-based light emitting material and charge transporting material
[Outside 57]

[0102]
In the organic light-emitting device of the present invention, the layer containing the condensed polycyclic compound represented by the general formula [I] to the general formula [VII] and the layer containing another organic compound are generally formed by a vacuum deposition method or a suitable method. A thin film is formed by a coating method after dissolving in a solvent. In particular, when a film is formed by a coating method, the film can be formed in combination with an appropriate binder resin.
[0103]
The binder resin can be selected from a wide range of binder resins such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, acrylic resin, methacrylic resin, butyral resin, polyvinyl acetal resin, diallyl phthalate resin. , Phenol resin, epoxy resin, silicone resin, polysulfone resin, urea resin and the like, but are not limited thereto. Moreover, you may mix these 1 type, or 2 or more types as a single or copolymer polymer.
[0104]
As the anode material, a material having a work function as large as possible is good. For example, simple metals such as gold, platinum, nickel, palladium, cobalt, selenium, vanadium or alloys thereof, tin oxide, zinc oxide, indium tin oxide (ITO), A metal oxide such as zinc indium oxide can be used. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. These electrode materials may be used alone or in combination.
[0105]
On the other hand, the cathode material preferably has a small work function, and can be used as a single metal or a plurality of alloys such as lithium, sodium, potassium, calcium, magnesium, aluminum, indium, silver, lead, tin, and chromium. It is also possible to use metal oxidation such as indium tin oxide (ITO). Further, the cathode may have a single layer structure or a multilayer structure.
[0106]
Although it does not specifically limit as a board | substrate used by this invention, Transparent substrates, such as opaque board | substrates, such as a metal board | substrate and a ceramic board | substrate, glass, quartz, a plastic sheet, are used. It is also possible to control the color light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film, or the like on the substrate.
[0107]
Note that a protective layer or a sealing layer can be provided on the prepared element for the purpose of preventing contact with oxygen or moisture. Examples of the protective layer include diamond thin films, inorganic material films such as metal oxides and metal nitrides, polymer films such as fluorine resin, polyparaxylene, polyethylene, silicone resin, polystyrene resin, and photo-curing resins. It is done. Further, it is possible to cover glass, a gas impermeable film, a metal, etc., and to package the element itself with an appropriate sealing resin.
[0108]
【Example】
EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
[0109]
[Example 1]
An element having the structure shown in FIG. 2 was produced.
[0110]
What formed indium tin oxide (ITO) as an anode 2 with a film thickness of 120 nm on a glass substrate as a substrate 1 by a sputtering method was used as a transparent conductive support substrate. This was ultrasonically washed successively with acetone and isopropyl alcohol (IPA), then boiled and washed with IPA and then dried. Furthermore, what was UV / ozone cleaned was used as a transparent conductive support substrate.
[0111]
A hole transport layer 5 was formed by depositing a chloroform solution of a compound represented by the following structural formula on a transparent conductive support substrate with a film thickness of 30 nm by spin coating.
[Outside 58]

[0112]
Furthermore, Exemplified Compound No. 11 was formed into a film having a thickness of 50 nm by a vacuum vapor deposition method to form an electron transport layer 6. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 0.2 to 0.3 nm / sec.
[0113]
Next, as the cathode 4, a metal layer film having a thickness of 150 nm was formed on the organic layer by a vacuum deposition method using a vapor deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%). Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 1.0 to 1.2 nm / sec.
[0114]
When a 10 V DC voltage was applied to the device thus obtained with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, 9.3 mA / cm²Current flows through the device at a current density of 1400 cd / m²Blue light emission was observed at a luminance of.
[0115]
Furthermore, the current density is 7.0 mA / cm under a nitrogen atmosphere.²When the voltage was applied for 100 hours, the initial luminance was 1100 cd / m.²1000 cd / m after 100 hours²And the luminance degradation was small.
[0116]
[Examples 2 to 10]
Exemplified Compound No. In place of Ex. A device was prepared in the same manner as in Example 1 except that 1, 13, 22, 26, 27, 32, 39, 42, and 44 were used, and the same evaluation was performed.
[0117]
The results are shown in Table-1.
[0118]
[Comparative Examples 1-8]
Exemplified Compound No. A device was prepared in the same manner as in Example 1 except that a compound represented by the following structural formula was used instead of 11, and the same evaluation was performed.
[0119]
The results are shown in Table-1.
[0120]
Comparative Compound No. 1
[Outside 59]

[0121]
Comparative Compound No. 2
[Outside 60]

[0122]
Comparative Compound No. 3
[Outside 61]

[0123]
Comparative Compound No. 4
[Outside 62]

[0124]
Comparative Compound No. 5
[Outside 63]

[0125]
Comparative Compound No. 6
[Outside 64]

[0126]
Comparative Compound No. 7
[Outside 65]

[0127]
Comparative Compound No. 8
[Outside 66]

[0128]
[Table 1]

[0129]
[Example 11]
An element having the structure shown in FIG. 3 was prepared.
[0130]
In the same manner as in Example 1, a hole transport layer 5 was formed on a transparent conductive support substrate.
[0131]
Furthermore, Exemplified Compound No. The light emitting layer 3 was formed by forming a condensed polycyclic compound represented by No. 11 with a film thickness of 20 nm by vacuum deposition. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 0.2 to 0.3 nm / sec.
[0132]
Furthermore, aluminum triskinolinol was formed into a film with a thickness of 40 nm by a vacuum vapor deposition method to form the electron transport layer 6. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 0.2 to 0.3 nm / sec.
[0133]
Next, as the cathode 4, a metal layer film having a thickness of 150 nm is formed on the organic layer by a vacuum deposition method using a deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%). An element having the structure shown was produced. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 1.0 to 1.2 nm / sec.
[0134]
When a direct current voltage of 8 V was applied to the device thus obtained with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, 8.4 mA / cm.²Current flows to the device at a current density of 8500 cd / m²Blue light emission was observed at a luminance of.
[0135]
Furthermore, the current density is 7.0 mA / cm under a nitrogen atmosphere.²When the voltage was applied for 100 hours, the initial luminance was 7600 cd / m.²6400 cd / m after 100 hours²And the luminance degradation was small.
[0136]
[Examples 12 to 20]
Exemplified Compound No. In place of Ex. A device was prepared in the same manner as in Example 11 except that 6, 9, 15, 20, 24, 35, 37, 43, and 46 were used, and the same evaluation was performed.
[0137]
The results are shown in Table-2.
[0138]
[Comparative Examples 9 to 16]
Exemplified Compound No. In place of Comparative compound No. 11 A device was prepared in the same manner as in Example 11 except that 1, 2, 3, 4, 5, 6, 7, and 8 were used, and the same evaluation was performed.
[0139]
The results are shown in Table-2.
[0140]
[Table 2]

[0141]
[Example 21]
An element having the structure shown in FIG. 3 was prepared.
[0142]
On a transparent conductive support substrate similar to that in Example 1, a chloroform solution of a compound represented by the following structural formula was formed to a thickness of 20 nm by spin coating to form a hole transport layer 5.
[Outside 67]

[0143]
Further, the compounds represented by the following structural formulas and exemplified compound Nos. The condensed polycyclic compound (weight ratio 1:50) represented by 11 was formed into a film with a thickness of 20 nm by a vacuum deposition method to form the light emitting layer 3. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 0.2 to 0.3 nm / sec.
[Outside 68]

[0144]
Furthermore, aluminum triskinolinol was formed into a film with a thickness of 40 nm by a vacuum vapor deposition method to form the electron transport layer 6. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 0.2 to 0.3 nm / sec.
[0145]
Next, as the cathode 4, a metal layer film having a thickness of 150 nm is formed on the organic layer by a vacuum deposition method using a deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%). An element having the structure shown was produced. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 1.0 to 1.2 nm / sec.
[0146]
When a direct current voltage of 8 V was applied to the device thus obtained with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, 8.8 mA / cm.²Current flows through the device at a current density of 82000 cd / m²Blue light emission was observed at a luminance of.
[0147]
Furthermore, the current density is 5.0 mA / cm under a nitrogen atmosphere.²When the voltage was applied for 100 hours, the initial luminance was 39000 cd / m.²100 hours after 33,000 cd / m²And the luminance degradation was small.
[0148]
[Examples 22 to 30]
Exemplified Compound No. In place of Ex. A device was prepared in the same manner as in Example 21 except that 2, 10, 14, 21, 25, 30, 36, 40, and 47 were used, and the same evaluation was performed.
[0149]
The results are shown in Table-3.
[0150]
[Comparative Examples 17-24]
Exemplified Compound No. In place of Comparative compound No. 11 A device was prepared in the same manner as in Example 21 except that 1, 2, 3, 4, 5, 6, 7, and 8 were used, and the same evaluation was performed.
The results are shown in Table-3.
[0151]
[Table 3]

[0152]
[Example 31]
An element having the structure shown in FIG. 5 was produced.
[0153]
In the same manner as in Example 21, the hole transport layer 5 was formed on the transparent conductive support substrate. Further, rubrene and aluminum triskinolinol (weight ratio 1:20) were formed into a film thickness of 20 nm by vacuum deposition to form the light emitting layer 3, The hole-exciton blocking layer 8 was formed by depositing the condensed polycyclic compound represented by 11 with a film thickness of 10 nm by vacuum deposition. Furthermore, aluminum triskinolinol was formed into a film with a thickness of 40 nm by a vacuum vapor deposition method to form the electron transport layer 6. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 0.2 to 0.3 nm / sec.
[0154]
Next, as the cathode 4, a metal layer film having a thickness of 150 nm is formed on the organic layer by a vacuum deposition method using a deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%). An element having the structure shown was produced. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 1.0 to 1.2 nm / sec.
[0155]
When a direct current voltage of 10 V was applied to the device thus obtained with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, 9.1 mA / cm²Current flows through the device at a current density of 81000 cd / m²Yellow-green light emission was observed at a luminance of.
[0156]
Furthermore, the current density is 7.0 mA / cm under a nitrogen atmosphere.²When the voltage was applied for 100 hours, the initial luminance was 51000 cd / m.²39000 cd / m after 100 hours²And the luminance degradation was small.
[0157]
[Examples 32 to 40]
Exemplified Compound No. In place of Ex. A device was prepared in the same manner as in Example 31 except that 3, 7, 18, 19, 28, 31, 38, 41, and 45 were used, and the same evaluation was performed.
[0158]
The results are shown in Table-4.
[0159]
[Comparative Examples 25-32]
Exemplified Compound No. In place of Comparative compound No. 11 A device was prepared in the same manner as in Example 31 except that 1, 2, 3, 4, 5, 6, 7, and 8 were used, and the same evaluation was performed.
The results are shown in Table-4.
[0160]
[Table 4]

[0161]
[Example 41]
An element having the structure shown in FIG. 3 was prepared.
[0162]
On a transparent conductive support substrate similar to that in Example 1, a chloroform solution of a compound represented by the following structural formula was formed to a thickness of 20 nm by spin coating to form a hole transport layer 5.
[Outside 69]

[0163]
Further, the compounds represented by the following structural formulas and exemplified compound Nos. The condensed polycyclic compound (weight ratio 1:50) represented by 11 was formed into a film with a thickness of 20 nm by a vacuum deposition method to form the light emitting layer 3. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 0.2 to 0.3 nm / sec.
[Outside 70]

[0164]
Furthermore, aluminum triskinolinol was formed into a film with a thickness of 40 nm by a vacuum vapor deposition method to form the electron transport layer 6. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 0.2 to 0.3 nm / sec.
[0165]
Next, as the cathode 4, a metal layer film having a thickness of 150 nm is formed on the organic layer by a vacuum deposition method using a deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%). An element having the structure shown was produced. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 1.0 to 1.2 nm / sec.
[0166]
When an 8V DC voltage was applied to the device thus obtained with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, 7.7 mA / cm was applied.²Current flows through the device at a current density of 12000 cd / m²Green light emission was observed at a brightness of.
[0167]
Furthermore, the current density is 5.0 mA / cm under a nitrogen atmosphere.²When the voltage was applied for 100 hours, the initial luminance was 8600 cd / m.²7800 cd / m after 100 hours²And the luminance degradation was small.
[0168]
[Examples 42 to 50]
Exemplified Compound No. In place of Ex. A device was prepared in the same manner as in Example 41 except that 4, 8, 12, 16, 23, 29, 34, 43, and 44 were used, and the same evaluation was performed.
[0169]
The results are shown in Table-5.
[0170]
[Comparative Examples 33 to 40]
Exemplified Compound No. In place of Comparative compound No. 11 A device was prepared in the same manner as in Example 41 except that 1, 2, 3, 4, 5, 6, 7, and 8 were used, and the same evaluation was performed.
The results are shown in Table-5.
[0171]
[Table 5]

[0172]
[Example 51]
An element having the structure shown in FIG. 1 was prepared.
[0173]
On the transparent conductive support substrate similar to Example 1, Exemplified Compound No. A solution obtained by dissolving 0.050 g of the condensed polycyclic compound represented by No. 11 and 1.00 g of poly-N-vinylcarbazole (weight average molecular weight = 63,000) in 80 ml of chloroform is 120 nm by spin coating (rotation speed = 2000 rpm). The organic layer (light emitting layer 3) was formed to a film thickness.
[0174]
Next, as the cathode 4, a metal layer film having a thickness of 150 nm is formed on the organic layer by a vacuum deposition method using a deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%). An element having the structure shown was produced. Degree of vacuum during deposition is 1.0 × 10^-4The film was formed under the conditions of Pa and film formation speed of 1.0 to 1.2 nm / sec.
[0175]
When a direct current voltage of 10 V was applied to the device thus obtained, with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, 7.5 mA / cm²Current flows through the device at a current density of 1400 cd / m²Blue light emission was observed at a luminance of.
[0176]
Furthermore, the current density is 5.0 mA / cm under a nitrogen atmosphere.²When the voltage was applied for 100 hours, the initial luminance was 920 cd / m.²870 cd / m after 100 hours²And the luminance degradation was small.
[0177]
[Examples 52 to 55]
Exemplified Compound No. In place of Ex. A device was prepared in the same manner as in Example 51 except that 5, 17, 33, and 47 were used, and the same evaluation was performed.
The results are shown in Table-6.
[0178]
[Comparative Examples 41 to 48]
Exemplified Compound No. In place of Comparative compound No. 11 A device was prepared in the same manner as in Example 51 except that 1, 2, 3, 4, 5, 6, 7, and 8 were used, and the same evaluation was performed.
The results are shown in Table-6.
[0179]
[Table 6]

[0180]
【The invention's effect】
As described above, the organic light emitting device using the condensed polycyclic compound represented by the general formulas [I] to [VII] can emit light with high luminance at a low applied voltage and has excellent durability. Yes. In particular, the organic layer containing the condensed polycyclic compound of the present invention is excellent as an electron transport layer and also excellent as a light emitting layer.
[0181]
Furthermore, the device can be formed using vacuum deposition, casting method, or the like, and a device with a large area can be easily manufactured at a relatively low cost.
[Brief description of the drawings]
FIG. 1 is a cross-sectional view showing an example of an organic light emitting device in the present invention.
FIG. 2 is a cross-sectional view showing another example of the organic light emitting device according to the present invention.
FIG. 3 is a cross-sectional view showing another example of the organic light emitting device according to the present invention.
FIG. 4 is a cross-sectional view showing another example of the organic light emitting device in the present invention.
FIG. 5 is a cross-sectional view showing another example of the organic light emitting device in the present invention.
FIG. 6 is a cross-sectional view showing another example of the organic light emitting device in the present invention.
[Explanation of symbols]
1 Substrate
2 Anode
3 Light emitting layer
4 Cathode
5 Hole transport layer
6 Electron transport layer
7 Hole injection layer
8 hole / exciton blocking layer

Claims (11)

A pair of electrodes including an anode and a cathode, at least with the organic light emitting element layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes, at least one layer below Symbol structure of a layer containing an organic compound the organic light emitting element characterized by containing the fused polycyclic compound represented in.
[Outside 1]

In an organic light-emitting device having at least one layer composed of an anode and a cathode and one or more organic compound layers sandwiched between the pair of electrodes, at least one layer containing the organic compound has the following general formula [ An organic light-emitting device comprising at least one of the condensed polycyclic compounds represented by formula II]:
Formula [II]
[Outside 2]

_(Wherein, R 5, _{R 6} are both hydrogen atom .R ₇ is a hydrogen atom or a pyridinyl group.
Ar ₃ and Ar ₄ are both fluoranthenyl groups, and any of the fluoranthenyl groups is bonded to the benzene ring represented by the general formula [II] at the 8-position .
Ar ₅ is any one of a pyrenyl group, a fluoranthenyl group, a phenanthrenyl group, a tetracenyl group, and a perylenyl group bonded to the benzene ring represented by the general formula [II] at the 8-position. ) The organic light-emitting device according to claim 2, wherein the condensed polycyclic compound is represented by the following structural formula.
[Outside 3]

In an organic light-emitting device having at least one layer composed of an anode and a cathode and one or more organic compound layers sandwiched between the pair of electrodes, at least one layer containing the organic compound has the following general formula [ III] An organic light-emitting device comprising at least one of the condensed polycyclic compounds represented by III].
Formula [III]
[Outside 4]

(Wherein, _{R 8} and _{R 9} are both water MotoHara child.
Ar ₆ and Ar ₇ are both fluoranthenyl groups, and any of the fluoranthenyl groups is bonded to the benzene ring represented by the general formula [III] at the 8-position . The fluoranthenyl group may have a phenyl group.
Ar ₈ and Ar ₉ are each independently selected from an anthracenyl group, a fluoranthenyl group bonded to the benzene ring represented by the general formula [III] at the 8-position, a pentacenyl group, and a naphthyl group. The anthracenyl group and the naphthyl group may have an alkyl group. ) The organic light-emitting device according to claim 4, wherein the condensed polycyclic compound is represented by the following structural formula.
[Outside 5]

A pair of electrodes including an anode and a cathode, at least with the organic light emitting element layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes, at least one layer below Symbol structure of a layer containing an organic compound the organic light emitting element characterized by containing the fused polycyclic compound represented in.
[Outside 6]

A pair of electrodes including an anode and a cathode, at least with the organic light emitting element layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes, at least one layer below Symbol structure of a layer containing an organic compound the organic light emitting element characterized by containing the fused polycyclic compound represented in.
[Outside 7]

A pair of electrodes including an anode and a cathode, at least with the organic light emitting element layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes, at least one layer below Symbol structure of a layer containing an organic compound in the indicated organic light emitting element, characterized in that it contains Ruizure or condensed polycyclic compounds.
[Outside 8]

[Outside 9]

A pair of electrodes including an anode and a cathode, at least with the organic light emitting element layer composed of one or a plurality of organic compounds sandwiched between the pair of electrodes, at least one layer below Symbol structure of a layer containing an organic compound in the indicated organic light emitting element, characterized in that it contains Ruizure or condensed polycyclic compounds.
[Outside 10]

[Outside 11]

[Outside 12]

[Outside 13]

The organic light-emitting device according to any one of claims 1 to 9, characterized in that said at least one layer comprising the organic compound is an electron transporting layer or the emitting layer. It has an organic light emitting element as described in any one of Claims 1 thru | or 10, and the board | substrate which has the said organic light emitting element, and also has any one of a color filter film, a fluorescence color conversion filter film, and a dielectric reflecting film. A structure characterized by that.

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