JP3899698B2 - Organic electroluminescent device material and organic electroluminescent device using the same - Google Patents
Organic electroluminescent device material and organic electroluminescent device using the same Download PDFInfo
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- JP3899698B2 JP3899698B2 JP24613898A JP24613898A JP3899698B2 JP 3899698 B2 JP3899698 B2 JP 3899698B2 JP 24613898 A JP24613898 A JP 24613898A JP 24613898 A JP24613898 A JP 24613898A JP 3899698 B2 JP3899698 B2 JP 3899698B2
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- 239000000463 material Substances 0.000 title claims description 64
- 238000005401 electroluminescence Methods 0.000 claims description 53
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000010409 thin film Substances 0.000 claims description 13
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- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 150000002894 organic compounds Chemical class 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
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- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
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- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 80
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- 239000000654 additive Substances 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical class C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005033 thiopyranyl group Chemical group 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
- BRODZLXTYKNNPW-UHFFFAOYSA-L zinc;2-(benzotriazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1N1N=C2C=CC=CC2=N1.[O-]C1=CC=CC=C1N1N=C2C=CC=CC2=N1 BRODZLXTYKNNPW-UHFFFAOYSA-L 0.000 description 1
- NVCBVYYESHBQKS-UHFFFAOYSA-L zinc;2-carboxyquinolin-8-olate Chemical compound [Zn+2].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 NVCBVYYESHBQKS-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
【０００１】
【産業上の利用分野】
本発明は平面光源や表示に使用される有機エレクトロルミネッセンス（ＥＬ）素子用発光材料および高輝度の発光素子に関するものである。
【０００２】
【従来の技術】
有機物質を使用したＥＬ素子は、固体発光型の安価な大面積フルカラー表示素子としての用途が有望視され、多くの開発が行われている。一般にＥＬ素子は、発光層および該層をはさんだ一対の対向電極から構成されている。発光は、両電極間に電界が印加されると、陰極側から電子が注入され、陽極側から正孔が注入される。さらに、この電子が発光層において正孔と再結合し、エネルギー準位が伝導帯から価電子帯に戻る際にエネルギーを光として放出する現象である。
【０００３】
従来の有機ＥＬ素子は、無機ＥＬ素子に比べて駆動電圧が高く、発光輝度や発光効率も低かった。また、特性劣化も著しく実用化には至っていなかった。
近年、１０Ｖ以下の低電圧で発光する高い蛍光量子効率を持った有機化合物を含有した薄膜を積層した有機ＥＬ素子が報告され、関心を集めている（アプライド・フィジクス・レターズ、５１巻、９１３ページ、１９８７年参照）。この方法は、金属キレート錯体を発光層、アミン系化合物を正孔注入層に使用して、高輝度の緑色発光を得ており、６〜７Ｖの直流電圧で輝度は数１０００ｃｄ／ｍ2、 最大発光効率は１．５ｌｍ／Ｗを達成して、実用領域に近い性能を持っている。
【０００４】
しかしながら、現在までの有機ＥＬ素子は、構成の改善により発光強度は改良されているが、未だ充分な発光輝度は有していない。また、繰り返し使用時の安定性に劣るという大きな問題を持っている。これは、例えば、トリス（８−ヒドロキシキノリナート）アルミニウム錯体等の金属キレート錯体が、電界発光時に化学的に不安定であり、陰極との密着性も悪く、短時間の発光で大きく劣化していた。以上の理由により、高い発光輝度、発光効率を持ち、繰り返し使用時での安定性の優れた有機ＥＬ素子の開発のために、優れた発光能力を有し、耐久性のある発光材料の開発が望まれている。
【０００５】
【発明が解決しようとする課題】
本発明は、発光輝度が高く、繰り返し使用時での安定性の優れた有機ＥＬ素子の提供にある。本発明者らが鋭意検討した結果、一般式［１］または［２］で示される有機ＥＬ素子用発光材料を発光層に使用した有機ＥＬ素子の発光輝度および発光効率が高く、繰り返し使用時での安定性も優れていることを見いだし本発明を成すに至った。
【０００６】
【課題を解決するための手段】
本発明は、下記一般式［１］で示される有機エレクトロルミネッセンス素子材料に関する。
一般式［１］
【０００７】
【化３】
［式中、Ｒ1〜Ｒ8は、それぞれ独立に、置換もしくは未置換のアルキル基、置換もしくは未置換のアルケニル基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアミノ基、置換もしくは未置換の酸素、窒素または硫黄原子を含んでも良いアリール基を表し、Ｒ1とＲ2、Ｒ3とＲ4、Ｒ5とＲ6、またはＲ7とＲ8はそれぞれ一体となっても良い。］更に本発明は、下記一般式［２］で示される有機エレクトロルミネッセンス素子材料に関する。
一般式［２］
【０００９】
【化４】
［式中、Ｒ9〜Ｒ14は、それぞれ独立に、置換もしくは未置換のアルキル基、置換 もしくは未置換のアルケニル基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアミノ基、置換もしくは未置換の酸素、窒素または硫黄原子を含んでも良いアリール基を表し、Ｒ9とＲ10、Ｒ11とＲ12、またはＲ13とＲ14はそれぞれ一体となっても良い。］
また、本発明は一対の電極間に発光層または発光層を含む複数層の有機化合物薄膜を形成してなる有機エレクトロルミネッセンス素子において、少なくとも一層が上記有機エレクトロルミネッセンス素子材料を含有する層である有機エレクトロルミネッセンス素子に関する。
【００１１】
また、本発明は一対の電極間に発光層または発光層を含む複数層の有機化合物薄膜を形成してなる有機エレクトロルミネッセンス素子において、発光層が上記有機エレクトロルミネッセンス素子材料を含有する層である有機エレクトロルミネッセンス素子に関する。
【００１２】
【発明の実施の形態】
本発明における一般式［１］および［２］で示される化合物のＲ1〜Ｒ14 は、それぞれ独立に置換もしくは未置換のアルキル基、置換もしくは未置換のアルケニル基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアミノ基、置換もしくは未置換の酸素、窒素または硫黄原子を含んでも良いアリール基を表す。
置換もしくは未置換のアルキル基としては、メチル基、エチル基、プロピル基、ブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ステアリル基、２−フェニルイソプロピル基、トリクロロメチル基、トリフルオロメチル基、ベンジル基、α−フェノキシベンジル基、α，α−ジメチルベンジル基、α，α−メチルフェニルベンジル基、α，α−ジトリフルオロメチルベンジル基、トリフェニルメチル基、α−ベンジルオキシベンジル基等の炭素数１〜２０のアルキル基およびその置換体がある。
【００１３】
置換もしくは未置換のアルケニル基としては、エチニル基、１−プロペニル基、１，３−ブタジエニル基、２−ペンテンー４−イニル基、３−メチル−２−ブテニル基、１−ペンチニル基、トリクロロエチニル基、トリフルオロエチニル基、３−α，α−ジトリフルオロメチル−２−ブテニル基等の炭素数１〜２０のアルケニル基およびその置換体がある。
【００１４】
置換もしくは未置換のアルコキシル基としては、メトキシ基、エトキシ基、プロポキシ基、ｎ−ブトキシ基、ｔ−ブトキシ基、ｎ−オクチルオキシ基、ｔ−オクチルオキシ基、１，１，１−テトラフルオロエトキシ基、フェノキシ基、ベンジルオキシ基、オクチルフェノキシ基等の炭素数１〜２０のアルコキシル基およびその置換体がある。
【００１５】
置換もしくは未置換のアルキルチオ基としては、メチルチオ基、エチルチオ基、プロピルチオ基、ｎ−ブチルチオ基、ｔ−ブチルチオ基、ｎ−オクチルチオ基、ｔ−オクチルチオ基、１，１，１−テトラフルオロエチルチオ基、フェニルチオ基、ベンジルチオ基、オクチルフェニルチオ基等の炭素数１〜２０のアルキルチオ基およびその置換体がある。
【００１６】
置換もしくは未置換のアミノ基としては、アミノ基、ビス（アセトキシメチル）アミノ基、ビス（アセトキシエチル）アミノ基、ビス（アセトキシプロピル）アミノ基、ビス（アセトキシブチル）アミノ基等があり、
メチルアミノ基、エチルアミノ基、ジエチルアミノ基、ジプロピルアミノ基、ジブチルアミノ基、ベンジルアミノ基、ジベンジルアミノ基等の炭素数１〜２０のアルキルアミノ基およびその置換体があり、
フェニルアミノ基、（３−メチルフェニル）アミノ基、（４−メチルフェニル）アミノ基、フェニルメチルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジビフェニルアミノ基、ジ（４−メチルビフェニル）アミノ基、ジ（３−メチルフェニル）アミノ基、ジ（４−メチルフェニル）アミノ基、ナフチルフェニルアミノ基、ビス［４−（α，α’−ジメチルベンジル）フェニル］アミノ基等のアリールアミノ基およびその置換体がある。
【００１７】
また、アミノ基として−Ｃ＝ＮＨ基を含む。また、アミノ基のＮ原子の２つの置換基は一体となってもよい。
【００１８】
置換もしくは未置換のアリール基としては、フェニル基、２−メチルフェニル基、３−メチルフェニル基、４−メチルフェニル基、４−エチルフェニル基、ビフェニル基、４−メチルビフェニル基、４−エチルビフェニル基、４−シクロヘキシルビフェニル基ターフェニル基、３，５−ジクロロフェニル基、ナフチル基、５−メチルナフチル基、アントリル基、ピレニル基等の炭素数１〜２０のアリール基およびその置換体がある。
【００１９】
さらに、アリール基は、窒素原子、酸素原子およびまたは硫黄原子により芳香族炭素原子が置換されていてもよい。このようなアリール基としては、フリル基、ピロール基、ピラニル基、チオピラニル基、チアゾリル基、イミダゾリール基、ピリミジニル基、ピリジニル基、トリアジニル基、インドリニル基、キノリル基、プリニル基等がある。
【００２０】
また、Ｒ1とＲ2、Ｒ3とＲ4、Ｒ5とＲ6、Ｒ7とＲ8、Ｒ9とＲ10、Ｒ11とＲ12、またはＲ13とＲ14はそれぞれ一体となって、置換もしくは未置換の、シクロペンテン環、シクロヘキセン環、ベンゼン環、ナフタレン環、アントラセン環、ピレン環、フルオレン環、フラン環、チオフェン環、ピロール環、オキサゾール環、チアゾール環、イミダゾール環、ピリジン環、ピラジン環、ピロリン環、ピラゾリン環、インドール環、キノリン環、キノキサリン環、キサンテン環、カルバゾール環、アクリジン環、フェナントロリン環等の飽和もしくは不飽和環を形成してもよい。
【００２１】
Ｒ1〜Ｒ14の有する置換基は、更にハロゲン原子、アルキル基、アルコキシ基、アリール基、アミノ基などで置換されていてもよい。
ハロゲン原子としては弗素、塩素 、臭素、ヨウ素がある。アルキル基、アルコキシ基、アリール基、アミノ基の具体例は、Ｒ1〜Ｒ14の具体例で示したものを挙げることができる。
【００２２】
一般式［１］および［２］で示される化合物は融点が非常に高く、強い青い蛍光を有するため、有機ＥＬ素子の発光材料として使用した場合、高い発光輝度を示し、長時間発光させる際にも有利である。
【００２３】
本発明の一般式［１］および［２］で示される化合物は、例えば、H.ErdmanがTetrahedron Letters,1970年,3389ページに報告した合成方法に準拠して得る事が出来るが、一般的な合成方法を以下に示す。一般式［３］のα−キノン化合物を、酢酸溶媒中、硫酸で脱水縮合させるか、ニトロベンゼン中で、塩化アルミニウムと反応させることにより合成することが可能である。これらの合成法は一例であり、特に限定されるものではない。
一般式［３］
【００２４】
【化５】
［式中、Ｒ15およびＲ16は、それぞれ独立に置換もしくは未置換のアルキル基、置換もしくは未置換のアルケニル基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアミノ基、置換もしくは未置換の酸素、窒素または硫黄原子を含んでも良いアリール基を表し、Ｒ1とＲ2一体となっても良い。］
【００２６】
以下に、本発明の一般式［１］および［２］で示される化合物の代表例を、表１に具体的に例示するが、本発明は、この代表例に限定されるものではない。
【００２７】
【表１】
本発明の一般式［１］および［２］で示される化合物は、固体状態において強い蛍光を持つ化合物であり電場発光性にも優れている。また、金属電極からの優れた正孔注入性および正孔輸送性、金属電極からの優れた電子注入性および電子輸送性を併せて持ち合わせているので、発光材料として有効に使用することができ、更には、他の正孔輸送性材料、電子輸送性材料もしくはドーピング材料を使用してもさしつかえない。
【００３５】
有機ＥＬ素子は、陽極と陰極間に一層もしくは多層の有機化合物薄膜を形成した素子である。一層型の場合、陽極と陰極との間に発光層を設けている。発光層は、発光材料を含有し、それに加えて陽極から注入した正孔、もしくは陰極から注入した電子を発光材料まで輸送させるために、正孔注入材料もしくは電子注入材料を含有しても良い。しかしながら、本発明の発光材料は、極めて高い発光量子効率、高い正孔輸送能力および電子輸送能力を併せ持ち、均一な薄膜を形成することができるので、本発明の発光材料のみで発光層を形成することも可能である。多層型は、（陽極／正孔注入帯域／発光層／陰極）、（陽極／発光層／電子注入帯域／陰極）、（陽極／正孔注入帯域／発光層／電子注入帯域／陰極）の多層構成で積層した有機ＥＬ素子がある。一般式［１］の化合物は、高い発光特性を持ち、正孔注入性、正孔輸送特性および電子注入性、電子輸送特性をもっているので、発光材料として発光層に使用できる。
【００３６】
発光層には、必要があれば、本発明の一般式［１］または［２］で示される化合物に加えて、さらなる公知の発光材料、ドーピング材料、正孔注入材料や電子注入材料を使用することもできる。有機ＥＬ素子は、多層構造にすることにより、クエンチングによる輝度や寿命の低下を防ぐことができる。必要があれば、発光材料、ドーピング材料、正孔注入材料や電子注入材料を組み合わせて使用することが出来る。また、ドーピング材料により、発光輝度や発光効率の向上、赤色や青色の発光を得ることもできる。また、正孔注入帯域、発光層、電子注入帯域は、それぞれ二層以上の層構成により形成されても良い。その際には、正孔注入帯域の場合、電極から正孔を注入する層を正孔注入層、正孔注入層から正孔を受け取り発光層まで正孔を輸送する層を正孔輸送層と呼ぶ。同様に、電子注入帯域の場合、電極から電子を注入する層を電子注入層、電子注入層から電子を受け取り発光層まで電子を輸送する層を電子輸送層と呼ぶ。これらの各層は、材料のエネルギー準位、耐熱性、有機層もしくは金属電極との密着性等の各要因により選択されて使用される。
【００３７】
一般式［１］または［２］で示される化合物と共に発光層に使用できる発光材料またはドーピング材料としては、アントラセン、ナフタレン、フェナントレン、ピレン、テトラセン、コロネン、クリセン、フルオレセイン、ペリレン、フタロペリレン、ナフタロペリレン、ペリノン、フタロペリノン、ナフタロペリノン、ジフェニルブタジエン、テトラフェニルブタジエン、クマリン、オキサジアゾール、アルダジン、ビスベンゾキサゾリン、ビススチリル、ピラジン、シクロペンタジエン、キノリン金属錯体、アミノキノリン金属錯体、ベンゾキノリン金属錯体、イミン、ジフェニルエチレン、ビニルアントラセン、ジアミノカルバゾール、ピラン、チオピラン、ポリメチン、メロシアニン、イミダゾールキレート化オキシノイド化合物、キナクリドン、ルブレンおよび色素レーザー用や増白用の蛍光色素等があるが、これらに限定されるものではない。
【００３８】
一般式［１］または［２］で示される化合物に発光層に使用できる上記の化合物の発光層中での存在比率はどれが主成分であってもよい。つまり、上記の化合物と一般式［１］または［２］で示される化合物との組み合わせにより、本発明における化合物は発光層を形成する主材料にも他の主材料中へのドーピンク材料にも成り得る。
【００３９】
正孔注入材料としては、正孔を輸送する能力を持ち、陽極からの正孔注入効果、発光層または発光材料に対して優れた正孔注入効果を有し、発光層で生成した励起子の電子注入帯域または電子注入材料への移動を防止し、かつ薄膜形成能力の優れた化合物が挙げられる。具体的には、フタロシアニン誘導体、ナフタロシアニン誘導体、ポルフィリン誘導体、オキサゾール、オキサジアゾール、トリアゾール、イミダゾール、イミダゾロン、イミダゾールチオン、ピラゾリン、ピラゾロン、テトラヒドロイミダゾール、ヒドラゾン、アシルヒドラゾン、ポリアリールアルカン、スチルベン、ブタジエン、ベンジジン型トリフェニルアミン、スチリルアミン型トリフェニルアミン、ジアミン型トリフェニルアミン等と、それらの誘導体、およびポリビニルカルバゾール、ポリシラン、導電性高分子等の高分子材料等があるが、これらに限定されるものではない。
【００４０】
本発明の有機ＥＬ素子において使用できる正孔注入材料の中で、さらに効果的な正孔注入材料は、芳香族三級アミン誘導体もしくはフタロシアニン誘導体である。芳香族三級アミン誘導体の具体例としては、トリフェニルアミン、トリトリルアミン、トリルジフェニルアミン、Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−１，１’−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラ（４−メチルフェニル）−１，１’−フェニル−４，４’−ジアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラ（４−メチルフェニル）−１，１’−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（１−ナフチル）−１，１’−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ’−ジ（メチルフェニル）−Ｎ，Ｎ’−ジ（４−ｎ−ブチルフェニル）フェナントレン−９，１０−ジアミン、４，４’，４”−トリス（Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ）トリフェニルアミン、１，１−ビス（４−ジ−ｐ−トリルアミノフェニル）シクロヘキサン等、もしくはこれらの芳香族三級アミン骨格を有したオリゴマーもしくはポリマー等があるが、これらに限定されるものではない。
【００４１】
フタロシアニン（Ｐｃ）誘導体の具体例としては、Ｈ2Ｐｃ、ＣｕＰｃ、Ｃｏ Ｐｃ、ＮｉＰｃ、ＺｎＰｃ、ＰｄＰｃ、ＦｅＰｃ、ＭｎＰｃ、ＣｌＡｌＰｃ、ＣｌＧａＰｃ、ＣｌＩｎＰｃ、ＣｌＳｎＰｃ、Ｃｌ2ＳｉＰｃ、（ＨＯ）ＡｌＰｃ 、（ＨＯ）ＧａＰｃ、ＶＯＰｃ、ＴｉＯＰｃ、ＭｏＯＰｃ、ＧａＰｃ−Ｏ−ＧａＰｃ等のフタロシアニン誘導体およびナフタロシアニン誘導体等があるが、これらに限定されるものではない。
【００４２】
電子注入材料としては、電子を輸送する能力を持ち、陰極からの正孔注入効果、発光層または発光材料に対して優れた電子注入効果を有し、発光層で生成した励起子の正孔注入帯域への移動を防止し、かつ薄膜形成能力の優れた化合物が挙げられる。例えば、フルオレノン、アントラキノジメタン、ジフェノキノン、チオピランジオキシド、オキサゾール、オキサジアゾール、トリアゾール、イミダゾール、ペリレンテトラカルボン酸、フレオレニリデンメタン、アントラキノジメタン、アントロン等とそれらの誘導体があるが、これらに限定されるものではない。また、正孔注入材料に電子受容物質を、電子注入材料に電子供与性物質を添加することにより増感させることもできる。
【００４３】
本発明の有機ＥＬ素子において、さらに効果的な電子注入材料は、金属錯体化合物もしくは含窒素五員環誘導体である。
具体的には、金属錯体化合物としては、８−ヒドロキシキノリナートリチウム、ビス（８−ヒドロキシキノリナート）亜鉛、ビス（８−ヒドロキシキノリナート）銅、ビス（８−ヒドロキシキノリナート）マンガン、トリス（８−ヒドロキシキノリナート）アルミニウム、トリス（２−メチル−８−ヒドロキシキノリナート）アルミニウム、トリス（８−ヒドロキシキノリナート）ガリウム、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナート）ベリリウム、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナート）亜鉛、ビス（２−メチル−８−ヒドロキシキノリナート）クロロガリウム、ビス（２−メチル−８−ヒドロキシキノリナート）（ｏ−クレゾラート）ガリウム、ビス（２−メチル−８−ヒドロキシキノリナート）（１−ナフトラート）アルミニウム、ビス（２−メチル−８−ヒドロキシキノリナート）（２−ナフトラート）ガリウム、ビス（２−メチル−８−ヒドロキシキノリナート）フェノラートガリウム、ビス（ｏ−（２−ベンゾオキサゾリル）フェノラート）亜鉛、ビス（ｏ−（２−ベンゾチアゾリル）フェノラート）亜鉛、ビス（ｏ−（２−ベンゾトリアゾリル）フェノラート）亜鉛等があるが、これらに限定されるものではない。
【００４４】
また、含窒素五員誘導体としては、オキサゾール、チアゾール、オキサジアゾール、チアジアゾールもしくはトリアゾール誘導体が好ましい。具体的には、２，５−ビス（１−フェニル）−１，３，４−オキサゾール、１，４−ビス（２−（４−メチル−５−フェニルオキサゾリル））ベンゼン、２，５−ビス（１−フェニル）−１，３，４−チアゾール、２，５−ビス（１−フェニル）−１，３，４−オキサジアゾール、２−（４’−ｔｅｒｔ−ブチルフェニル）−５−(４”−ビフェ ニル)１，３，４−オキサジアゾール、２，５−ビス（１−ナフチル）−１，３ ，４−オキサジアゾール、１，４−ビス［２−(５−フェニルオキサジアゾリル)］ベンゼン、１，４−ビス［２−(５−フェニルオキサジアゾリル)−４−ｔｅｒｔ−ブチルベンゼン］、２−（４’−ｔｅｒｔ−ブチルフェニル）−５−(４” −ビフェニル)−１，３，４−チアジアゾール、２，５−ビス（１−ナフチル） −１，３，４−チアジアゾール、１，４−ビス［２−(５−フェニルチアジアゾ リル)］ベンゼン、３−（４’−ｔｅｒｔ−ブチルフェニル）−５−(４”−ビフェニル)−４−フェニル−１，２，４−トリアゾール、３，５−ビス（１−ナフ チル）−４−ｍ−トリル−１，２，４−トリアゾール等があるが、これらに限定されるものではない。
【００４５】
本有機ＥＬ素子においては、発光層中に、一般式［１］または［２］で示される化合物の他に、発光材料、ドーピング材料、正孔注入材料および電子注入材料の少なくとも１種が同一層に含有されてもよい。また、本発明により得られた有機ＥＬ素子の、温度、湿度、雰囲気等に対する安定性の向上のために、素子の表面に保護層を設けたり、シリコンオイル、樹脂等により素子全体を保護することも可能である。
【００４６】
有機ＥＬ素子の陽極に使用される導電性材料としては、４ｅＶより大きな仕事関数を持つものが適しており、炭素、アルミニウム、バナジウム、鉄、コバルト、ニッケル、タングステン、銀、金、白金、パラジウム等およびそれらの合金、ＩＴＯ基板、ＮＥＳＡ基板に使用される酸化スズ、酸化インジウム等の酸化金属、さらにはポリチオフェンやポリピロール等の有機導電性樹脂が用いられる。
【００４７】
陰極に使用される導電性物質としては、４ｅＶより小さな仕事関数を持つものが適しており、マグネシウム、カルシウム、錫、鉛、チタニウム、イットリウム、リチウム、ルテニウム、マンガン、アルミニウム等およびそれらの合金が用いられるが、これらに限定されるものではない。合金としては、マグネシウム／銀、マグネシウム／インジウム、リチウム／アルミニウム等が代表例として挙げられるが、これらに限定されるものではない。合金の比率は、蒸着源の温度、雰囲気、真空度等により制御され、適切な比率に選択される。陽極および陰極は、必要があれば二層以上の層構成により形成されていても良い。
【００４８】
有機ＥＬ素子では、効率良く発光させるために、少なくとも一方は素子の発光波長領域において充分透明にすることが望ましい。また、基板も透明であることが望ましい。透明電極は、上記の導電性材料を使用して、蒸着やスパッタリング等の方法で所定の透光性が確保するように設定する。発光面の電極は、光透過率を１０％以上にすることが望ましい。基板は、機械的、熱的強度を有し、透明性を有するものであれば限定されるものではないが、例示すると、ガラス基板、ポリエチレン板、ポリエチレンテレフテレート板、ポリエーテルサルフォン板、ポリプロピレン板等の透明樹脂があげられる。
【００４９】
本発明に係わる有機ＥＬ素子の各有機化合物薄膜の形成は、真空蒸着、スパッタリング、プラズマ、イオンプレーティング等の乾式成膜法やスピンコーティング、ディッピング、フローコーティング等の湿式成膜法のいずれの方法を適用することができる。膜厚は特に限定されるものではないが、適切な膜厚に設定する必要がある。膜厚が厚すぎると、一定の光出力を得るために大きな印加電圧が必要になり効率が悪くなる。膜厚が薄すぎるとピンホール等が発生して、電界を印加しても充分な発光輝度が得られない。通常の膜厚は５ｎｍから１０μｍの範囲が適しているが、１０ｎｍから０．２μｍの範囲がさらに好ましい。
【００５０】
湿式成膜法の場合、各有機化合物薄膜を形成する材料を、エタノール、クロロホルム、テトラヒドロフラン、ジオキサン等の適切な溶媒に溶解または分散させて薄膜を形成するが、その溶媒はいずれであっても良い。また、いずれの有機化合物薄膜においても、成膜性向上、膜のピンホール防止等のため適切な樹脂や添加剤を使用しても良い。使用の可能な樹脂としては、ポリスチレン、ポリカーボネート、ポリアリレート、ポリエステル、ポリアミド、ポリウレタン、ポリスルフォン、ポリメチルメタクリレート、ポリメチルアクリレート、セルロース等の絶縁性樹脂およびそれらの共重合体、ポリ−Ｎ−ビニルカルバゾール、ポリシラン等の光導電性樹脂、ポリチオフェン、ポリピロール等の導電性樹脂を挙げることができる。また、添加剤としては、酸化防止剤、紫外線吸収剤、可塑剤等を挙げることができる。
【００５１】
以上のように、有機ＥＬ素子の発光層に本発明の化合物を用いることにより、発光効率、最大発光輝度等の有機ＥＬ素子特性を改良することができた。また、この素子は熱や電流に対して非常に安定であり、さらには低い駆動電圧で実用的に使用可能の発光輝度が得られるため、従来まで大きな問題であった劣化も大幅に低下させることができた。
【００５２】
本発明の有機ＥＬ素子は、壁掛けテレビ等のフラットパネルディスプレイや、平面発光体として、複写機やプリンター等の光源、液晶ディスプレイや計器類等の光源、表示板、標識灯等へ応用が考えられ、その工業的価値は非常に大きい。
【００５３】
本発明の材料は、有機ＥＬ素子、電子写真感光体、光電変換素子、太陽電池、イメージセンサー等の分野においても使用できる。
【００５４】
【実施例】
以下、本発明を実施例に基づきさらに詳細に説明する。
【００５５】
化合物（４）の合成方法
１，４−ナフトキノン５部を酢酸５０部に溶解し、濃硫酸３０部と酢酸３５部の混合溶液を加えて５０時間加熱撹拌した。その後、５００部の水で希釈した。酢酸エチルで抽出を行い、濃縮して、シリカゲルを用いたカラムクロマトグラフィーにより精製を行ない白色の蛍光を有する粉末３部を得た。ＦＤ−ＭＳよる分子量分析により、化合物（４）であることを確認した。
【００５６】
以下に本発明の化合物を用いた実施例を示す。本例では、電極面積２ｍｍ×２ｍｍの有機ＥＬ素子の特性を測定した。
【００５７】
実施例１
洗浄したＩＴＯ電極付きガラス板上に、発光材料として表１の化合物（３）、２，５−ビス（１−ナフチル）−１，３，４−オキサジアゾール、ポリカーボネート樹脂（帝人化成：パンライトＫ−１３００）を５：３：２の重量比でテトラヒドロフランに溶解させ、スピンコーティング法により膜厚１００ｎｍの発光層を得た。その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１５０ｎｍの電極を形成して有機ＥＬ素子を得た。この素子の発光特性は、直流電圧５Ｖで８０（ｃｄ／ｍ2）、最高輝度１３００（ｃｄ／ｍ2）、発光効率０．５０（ｌｍ／Ｗ）の発光が得られた。
【００５８】
実施例２
洗浄したＩＴＯ電極付きガラス板上に、Ｎ，Ｎ'―ジ（３―メチルフェニル） ―Ｎ，Ｎ'―ジフェニル―１，１―ビフェニル-４，４―ジアミン（ＴＰＤ）を真空蒸着して、膜厚２０ｎｍの正孔注入層を得た。次いで、化合物（２）を蒸着し膜厚４０ｎｍの発光層を作成し、トリス（８−ヒドロキシキノリナート）アルミニウム錯体（Ａｌｑ３）を蒸着し、膜厚３０ｎｍの電子注入層を得た。その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入層および発光層は１０-6Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は直流電圧５Ｖで発光輝度１００（ｃｄ／ｍ2）、最大発光輝度７０００（ｃｄ／ｍ2）、５Ｖの時の発光効率１．０（ｌｍ／Ｗ）の青色発光が得られた。
【００５９】
実施例３
洗浄したＩＴＯ電極付きガラス板上に、化合物（７）を塩化メチレンに溶解させ、スピンコーティング法により膜厚５０ｎｍの正孔注入型発光層を得た。次いで、ビス（２−メチル−８−ヒドロキシキノリナート）（１−ナフトラート）ガリウム錯体を真空蒸着して膜厚１０ｎｍの電子注入層を作成し、その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。発光層および電子注入層は１０-6Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧５Ｖで１５０（ｃｄ／ｍ2 ）、最高輝度１００００（ｃｄ／ｍ2）、発光効率０．８０（ｌｍ／Ｗ）の青緑色 発光が得ら れた。
【００６０】
実施例４
洗浄したＩＴＯ電極付きガラス板上に、化合物（３）を真空蒸着して、膜厚５０ｎｍの正孔注入型発光層を得た。次いで、ビス（２−メチル−８−ヒドロキシキノリナート）（１−ナフトラート）ガリウム錯体を真空蒸着して膜厚１０ｎｍの電子注入層を作成し、その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。発光層および電子注入層は１０-6Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧５Ｖで２００（ｃｄ／ｍ2）、最高輝度１００００（ｃｄ／ｍ2）、発光効率１．１０（ｌｍ／Ｗ）の発光が得られた。
【００６１】
実施例５〜１５
洗浄したＩＴＯ電極付きガラス板上に、４，４’−ビス［Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ］ビフェニル（α−ＮＰＤ）を真空蒸着して、膜厚２０ｎｍに正孔注入層を形成した。次いで、発光材料として、表２の化合物を真空蒸着して膜厚２０ｎｍの発光層を得た。次いで、ビス（２−メチル−８−ヒドロキシキノリナート）（１−ナフトラート）ガリウム錯体を真空蒸着して膜厚１０ｎｍの電子注入層を作成し、その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入層および発光層は１０-6Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子の発光特性を表２に示す。ここでの発光輝度は、直流電圧５Ｖ印可時の輝度である。本実施例の有機ＥＬ素子は、全て最高輝度１００００（ｃｄ／ｍ2）以上の 高輝度特性を有し、また、青色から緑色の発光色を得ることができた。
【００６２】
【表２】
実施例１６
洗浄したＩＴＯ電極付きガラス板上に、４、４’、４”−トリス［Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ］トリフェニルアミンを真空蒸着して、膜厚４０ｎｍの正孔注入層を得た。次いで、４，４’−ビス［Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ］ビフェニル（α−ＮＰＤ）を真空蒸着して、膜厚１０ｎｍの第二正孔注入層を得た。さらに、化合物（１）を真空蒸着して、膜厚３０ｎｍの発光層を作成し、さらにビス（２−メチル−８−ヒドロキシキノリナト）（１−フェノラート）ガリウム錯体を真空蒸着して膜厚３０ｎｍの電子注入層を作成し、その上に、アルミニウムとリチウムを２５：１で混合した合金で膜厚１５０ｎｍの電極を形成して、有機ＥＬ素子を得た。正孔注入層および発光層は１０-6Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧５Ｖで発光輝度４１０（ｃｄ／ｍ2）、最大発光輝度１８０００（ｃｄ／ ｍ2）、発光効率１．８（ｌｍ／Ｗ）の青色発光が得られた。
【００６４】
実施例１７
ＩＴＯ電極と４，４’−ビス［Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ］ビフェニル（α−ＮＰＤ）との間に、無金属フタロシアニンの膜厚５ｎｍの正孔注入層を設ける以外は、実施例３と同様の方法で有機ＥＬ素子を作製した。この素子は、直流電圧５Ｖで８００（ｃｄ／ｍ2）、最高輝度１３０００（ｃ ｄ／ｍ2）、発光効率１．００（ｌｍ／Ｗ）の青緑色発光が得られた。
【００６５】
実施例１８
４、４’、４”−トリス［Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ］トリフェニルアミンの代わりに無金属フタロシアニンの膜厚２０ｎｍの正孔注入層を設ける以外は、実施例１６と同様の方法で有機ＥＬ素子を作製した。この素子は、直流電圧５Ｖで２５０（ｃｄ／ｍ2）、最高輝度１５０００（ｃｄ／ｍ 2）、発光効率１．５０（ｌｍ／Ｗ）の青緑色発光が得られた。
【００６６】
実施例１９
発光層として、化合物（３）：化合物（４）を１：５の割合で蒸着した膜厚１０ｎｍの正孔注入層を設ける以外は、実施例１６と同様の方法で有機ＥＬ素子を作製した。この素子は、直流電圧５Ｖで９００（ｃｄ／ｍ2）、最高 輝度１８０００（ｃｄ／ｍ2）、発光効率１．８０（ｌｍ／Ｗ）の青緑色発光が 得られた。
【００６７】
実施例２０
発光層として、化合物（３）：ビス（２−メチル−８−ヒドロキシキノリナート）（フェノラート）ガリウム錯体を１：１００の割合で蒸着した膜厚１０ｎｍの正孔注入層を設ける以外は、実施例１６と同様の方法で有機ＥＬ素子を作製した。この素子は、直流電圧５Ｖで２６０（ｃｄ／ｍ2）、最高輝度２００００（ ｃｄ／ｍ 2）、発光効率１．９０（ｌｍ／Ｗ）の青色発光が得られた。
【００６８】
本実施例で示された有機ＥＬ素子は、二層型以上の素子構成において、最大発光輝度１００００（ｃｄ／ｍ2）以上の発光が得られ、高い発光効率を得る ことができた。本実施例で示された有機ＥＬ素子について、３（ｍＡ／ｃｍ2） で連続発光させたところ、１０００時間以上安定な発光を観測することができた。
本発明の有機ＥＬ素子は発光効率、発光輝度の向上と長寿命化を達成するものであり、併せて使用される発光材料、ドーピング材料、正孔注入材料、電子注入材料、増感剤、樹脂、電極材料等および素子作製方法を限定するものではない。
【００６９】
【発明の効果】
本発明の有機ＥＬ用発光材料を発光材料として使用した有機ＥＬ素子は、従来に比べて高い発光効率で高輝度の発光を示し、長寿命の有機ＥＬ素子を得ることができた。[0001]
[Industrial application fields]
The present invention relates to a light-emitting material for organic electroluminescence (EL) elements used for flat light sources and displays, and a light-emitting element with high luminance.
[0002]
[Prior art]
An EL element using an organic substance is considered to be promising for use as an inexpensive large-area full-color display element of a solid light emitting type, and many developments have been made. In general, an EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Furthermore, this electron is recombined with holes in the light emitting layer, and energy is emitted as light when the energy level returns from the conduction band to the valence band.
[0003]
Conventional organic EL elements have a higher driving voltage and lower light emission luminance and light emission efficiency than inorganic EL elements. Further, the characteristic deterioration has been remarkably not put into practical use.
In recent years, an organic EL device in which a thin film containing an organic compound having a high fluorescence quantum efficiency that emits light at a low voltage of 10 V or less has been reported and attracted attention (Applied Physics Letters, Vol. 51, page 913). 1987). This method uses a metal chelate complex as a light emitting layer and an amine compound as a hole injection layer to obtain high luminance green light emission. The luminance is several thousand cd / m at a DC voltage of 6 to 7V.2The maximum luminous efficiency is 1.5 lm / W, and the performance is close to the practical range.
[0004]
However, the organic EL devices up to now have improved light emission intensity due to the improvement of the structure, but do not yet have sufficient light emission luminance. Moreover, it has a big problem that it is inferior in stability during repeated use. This is because, for example, metal chelate complexes such as tris (8-hydroxyquinolinate) aluminum complex are chemically unstable during electroluminescence, poor adhesion to the cathode, and greatly deteriorated in a short time of light emission. It was. For the above reasons, in order to develop an organic EL device having high luminous brightness and luminous efficiency and excellent stability during repeated use, the development of a light-emitting material with excellent luminous ability and durability has been developed. It is desired.
[0005]
[Problems to be solved by the invention]
An object of the present invention is to provide an organic EL device having high emission luminance and excellent stability in repeated use. As a result of intensive studies by the present inventors, the organic EL device using the light emitting material for the organic EL device represented by the general formula [1] or [2] as the light emitting layer has high emission luminance and light emission efficiency, and can be used repeatedly. The present inventors have found that the stability of is excellent, and have achieved the present invention.
[0006]
[Means for Solving the Problems]
The present invention relates to an organic electroluminescence element material represented by the following general formula [1].
General formula [1]
[0007]
[Chemical Formula 3]
[Wherein R1~ R8Each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted Represents an aryl group which may contain oxygen, nitrogen or sulfur atoms of R1And R2, RThreeAnd RFour, RFiveAnd R6Or R7And R8May be integrated together. Furthermore, this invention relates to the organic electroluminescent element material shown by following General formula [2].
General formula [2]
[0009]
[Formula 4]
[Wherein R9~ R14Each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted Represents an aryl group which may contain oxygen, nitrogen or sulfur atoms of R9And RTen, R11And R12Or R13And R14May be integrated together. ]
Further, the present invention relates to an organic electroluminescent device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes, and at least one layer is an organic layer containing the organic electroluminescent device material. The present invention relates to an electroluminescence element.
[0011]
Further, the present invention provides an organic electroluminescent device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes, wherein the light emitting layer is a layer containing the organic electroluminescent device material. The present invention relates to an electroluminescence element.
[0012]
DETAILED DESCRIPTION OF THE INVENTION
R of the compounds represented by the general formulas [1] and [2] in the present invention1~ R14 Each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted Represents an aryl group which may contain oxygen, nitrogen or sulfur atoms.
Examples of substituted or unsubstituted alkyl groups include methyl, ethyl, propyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, stearyl, and 2-phenyl. Isopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α, α-ditrifluoromethylbenzyl group, triphenyl Examples thereof include alkyl groups having 1 to 20 carbon atoms such as a methyl group and an α-benzyloxybenzyl group, and substituted products thereof.
[0013]
Examples of the substituted or unsubstituted alkenyl group include ethynyl group, 1-propenyl group, 1,3-butadienyl group, 2-pentene-4-ynyl group, 3-methyl-2-butenyl group, 1-pentynyl group, and trichloroethynyl group. , An alkenyl group having 1 to 20 carbon atoms such as a trifluoroethynyl group and a 3-α, α-ditrifluoromethyl-2-butenyl group, and substituted products thereof.
[0014]
Examples of the substituted or unsubstituted alkoxyl group include methoxy group, ethoxy group, propoxy group, n-butoxy group, t-butoxy group, n-octyloxy group, t-octyloxy group, 1,1,1-tetrafluoroethoxy Group, a phenoxy group, a benzyloxy group, an octylphenoxy group and the like, and an alkoxyl group having 1 to 20 carbon atoms and its substituent.
[0015]
As the substituted or unsubstituted alkylthio group, methylthio group, ethylthio group, propylthio group, n-butylthio group, t-butylthio group, n-octylthio group, t-octylthio group, 1,1,1-tetrafluoroethylthio group , A phenylthio group, a benzylthio group, an octylphenylthio group and the like, and an alkylthio group having 1 to 20 carbon atoms and substituted products thereof.
[0016]
Examples of substituted or unsubstituted amino groups include amino groups, bis (acetoxymethyl) amino groups, bis (acetoxyethyl) amino groups, bis (acetoxypropyl) amino groups, bis (acetoxybutyl) amino groups,
There are alkylamino groups having 1 to 20 carbon atoms such as methylamino group, ethylamino group, diethylamino group, dipropylamino group, dibutylamino group, benzylamino group, dibenzylamino group, and substituted products thereof,
Phenylamino group, (3-methylphenyl) amino group, (4-methylphenyl) amino group, phenylmethylamino group, diphenylamino group, ditolylamino group, dibiphenylamino group, di (4-methylbiphenyl) amino group, di Arylamino groups such as (3-methylphenyl) amino group, di (4-methylphenyl) amino group, naphthylphenylamino group, bis [4- (α, α'-dimethylbenzyl) phenyl] amino group, and substituted products thereof There is.
[0017]
Moreover, -C = NH group is included as an amino group. Moreover, two substituents of the N atom of the amino group may be combined.
[0018]
Examples of substituted or unsubstituted aryl groups include phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, biphenyl, 4-methylbiphenyl, 4-ethylbiphenyl. Group, 4-cyclohexylbiphenyl group, terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group and the like, and substituted groups thereof.
[0019]
Furthermore, in the aryl group, an aromatic carbon atom may be substituted with a nitrogen atom, an oxygen atom and / or a sulfur atom. Examples of such aryl groups include furyl, pyrrole, pyranyl, thiopyranyl, thiazolyl, imidazolyl, pyrimidinyl, pyridinyl, triazinyl, indolinyl, quinolyl, and purinyl groups.
[0020]
R1And R2, RThreeAnd RFour, RFiveAnd R6, R7And R8, R9And RTen, R11And R12Or R13And R14Are combined, substituted or unsubstituted, cyclopentene ring, cyclohexene ring, benzene ring, naphthalene ring, anthracene ring, pyrene ring, fluorene ring, furan ring, thiophene ring, pyrrole ring, oxazole ring, thiazole ring, imidazole. A saturated or unsaturated ring such as a ring, a pyridine ring, a pyrazine ring, a pyrroline ring, a pyrazoline ring, an indole ring, a quinoline ring, a quinoxaline ring, a xanthene ring, a carbazole ring, an acridine ring, or a phenanthroline ring may be formed.
[0021]
R1~ R14The substituent which may have may be further substituted with a halogen atom, an alkyl group, an alkoxy group, an aryl group, an amino group, or the like.
Halogen atoms include fluorine, chlorine, bromine and iodine. Specific examples of the alkyl group, alkoxy group, aryl group, and amino group are R1~ R14Examples shown in the specific examples can be given.
[0022]
Since the compounds represented by the general formulas [1] and [2] have a very high melting point and strong blue fluorescence, when used as a light-emitting material of an organic EL device, the compound exhibits high emission luminance and emits light for a long time. Is also advantageous.
[0023]
The compounds represented by the general formulas [1] and [2] of the present invention can be obtained, for example, according to the synthesis method reported by H. Erdman in Tetrahedron Letters, 1970, page 3389. The synthesis method is shown below. The α-quinone compound of the general formula [3] can be synthesized by dehydration condensation with sulfuric acid in an acetic acid solvent or by reacting with aluminum chloride in nitrobenzene. These synthesis methods are merely examples and are not particularly limited.
General formula [3]
[0024]
[Chemical formula 5]
[Wherein R15And R16Each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted Represents an aryl group which may contain oxygen, nitrogen or sulfur atoms, R1And R2It may be united. ]
[0026]
Specific examples of the compounds represented by the general formulas [1] and [2] of the present invention are specifically shown in Table 1 below, but the present invention is not limited to these representative examples.
[0027]
[Table 1]
The compounds represented by the general formulas [1] and [2] of the present invention are compounds having strong fluorescence in the solid state and excellent in electroluminescence. In addition, since it has excellent hole injection and hole transport properties from the metal electrode, and excellent electron injection and electron transport properties from the metal electrode, it can be used effectively as a luminescent material. Furthermore, other hole transport materials, electron transport materials or doping materials may be used.
[0035]
An organic EL element is an element in which a single-layer or multilayer organic compound thin film is formed between an anode and a cathode. In the case of the single layer type, a light emitting layer is provided between the anode and the cathode. The light-emitting layer contains a light-emitting material, and may further contain a hole-injecting material or an electron-injecting material in order to transport holes injected from the anode or electrons injected from the cathode to the light-emitting material. However, since the light emitting material of the present invention has extremely high emission quantum efficiency, high hole transport ability and electron transport ability and can form a uniform thin film, the light emitting layer is formed only by the light emitting material of the present invention. It is also possible. The multi-layer type includes (anode / hole injection band / light emitting layer / cathode), (anode / light emitting layer / electron injection band / cathode), and (anode / hole injection band / light emitting layer / electron injection band / cathode). There are organic EL elements stacked in a configuration. The compound of the general formula [1] has high light emission properties and has hole injection properties, hole transport properties, electron injection properties, and electron transport properties, and therefore can be used as a light emitting material in a light emitting layer.
[0036]
If necessary, in addition to the compound represented by the general formula [1] or [2] of the present invention, a further known light emitting material, doping material, hole injection material or electron injection material is used for the light emitting layer. You can also. By making the organic EL element have a multi-layer structure, it is possible to prevent a decrease in luminance and lifetime due to quenching. If necessary, a light emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination. Further, by using a doping material, it is possible to improve light emission luminance and light emission efficiency and to obtain red and blue light emission. Moreover, the hole injection zone, the light emitting layer, and the electron injection zone may each be formed with a layer configuration of two or more layers. In that case, in the case of the hole injection zone, the layer that injects holes from the electrode is a hole injection layer, and the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer. Call. Similarly, in the case of an electron injection zone, a layer for injecting electrons from an electrode is referred to as an electron injection layer, and a layer for receiving electrons from the electron injection layer and transporting electrons to a light emitting layer is referred to as an electron transport layer. Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.
[0037]
Examples of the light emitting material or doping material that can be used in the light emitting layer together with the compound represented by the general formula [1] or [2] include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone. , Phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene , Vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, imidazole chelating oxinoid compounds, Nakuridon, there is a fluorescent dye or the like for rubrene and dye laser for and brightening, but is not limited thereto.
[0038]
Any of the abundance ratios of the compound represented by the general formula [1] or [2] in the light emitting layer that can be used in the light emitting layer may be the main component. That is, the combination of the above compound and the compound represented by the general formula [1] or [2] makes the compound in the present invention a main material for forming a light emitting layer and a dopink material in another main material. obtain.
[0039]
As a hole injection material, it has the ability to transport holes, has a hole injection effect from the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and excitons generated in the light emitting layer. Examples thereof include compounds that prevent movement to an electron injection zone or an electron injection material and have an excellent thin film forming ability. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene, Benzidine-type triphenylamine, styrylamine-type triphenylamine, diamine-type triphenylamine, and derivatives thereof, and polymer materials such as polyvinyl carbazole, polysilane, and conductive polymer, but are not limited thereto. It is not a thing.
[0040]
Among the hole injection materials that can be used in the organic EL device of the present invention, a more effective hole injection material is an aromatic tertiary amine derivative or a phthalocyanine derivative. Specific examples of the aromatic tertiary amine derivative include triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N′-di (3-methylphenyl) -1,1′-biphenyl-4 , 4′-diamine, N, N, N ′, N′-tetra (4-methylphenyl) -1,1′-phenyl-4,4′-diamine, N, N, N ′, N′-tetra ( 4-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N, N′-diphenyl-N, N′-di (1-naphthyl) -1,1′-biphenyl-4,4 ′ -Diamine, N, N'-di (methylphenyl) -N, N'-di (4-n-butylphenyl) phenanthrene-9,10-diamine, 4,4 ', 4 "-tris (N- (3 -Methylphenyl) -N-phenylamino) tripheny Amine, 1,1-bis (4-di -p- tolyl-aminophenyl) cyclohexane, or there are oligomers or polymers, etc. having these aromatic tertiary amine skeletons, but is not limited thereto.
[0041]
Specific examples of phthalocyanine (Pc) derivatives include H2Pc, CuPc, Co Pc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2Examples include, but are not limited to, phthalocyanine derivatives such as SiPc, (HO) AlPc, (HO) GaPc, VOPc, TiOPc, MoOPc, and GaPc-O-GaPc, and naphthalocyanine derivatives.
[0042]
As an electron injection material, it has the ability to transport electrons, has a hole injection effect from the cathode, and an excellent electron injection effect for the light-emitting layer or light-emitting material, and hole injection of excitons generated in the light-emitting layer Examples thereof include compounds that prevent migration to the zone and have an excellent thin film forming ability. For example, there are fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone, and their derivatives. However, it is not limited to these. Further, it can be sensitized by adding an electron accepting substance to the hole injecting material and an electron donating substance to the electron injecting material.
[0043]
In the organic EL device of the present invention, a more effective electron injection material is a metal complex compound or a nitrogen-containing five-membered ring derivative.
Specifically, as the metal complex compound, 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinate) zinc, bis (8-hydroxyquinolinate) copper, bis (8-hydroxyquinolinate) manganese , Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] quinolinato) beryllium Bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-hydroxyquinolinato) chlorogallium, bis (2-methyl-8-hydroxyquinolinato) (o-cresolate) gallium, Bis (2-methyl-8-hydroxyquinolinate) (1-naphthlar ) Aluminum, bis (2-methyl-8-hydroxyquinolinato) (2-naphtholato) gallium, bis (2-methyl-8-hydroxyquinolinato) phenolate gallium, bis (o- (2-benzoxazolyl) (L) phenolate) zinc, bis (o- (2-benzothiazolyl) phenolate) zinc, bis (o- (2-benzotriazolyl) phenolate) zinc, and the like, but are not limited thereto.
[0044]
Further, as the nitrogen-containing five-membered derivative, an oxazole, thiazole, oxadiazole, thiadiazole or triazole derivative is preferable. Specifically, 2,5-bis (1-phenyl) -1,3,4-oxazole, 1,4-bis (2- (4-methyl-5-phenyloxazolyl)) benzene, 2,5 -Bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1-phenyl) -1,3,4-oxadiazole, 2- (4'-tert-butylphenyl) -5 -(4 "-biphenyl) 1,3,4-oxadiazole, 2,5-bis (1-naphthyl) -1,3,4-oxadiazole, 1,4-bis [2- (5- Phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxadiazolyl) -4-tert-butylbenzene], 2- (4'-tert-butylphenyl) -5- (4 " -Biphenyl) -1,3,4-thiadiazole, 2,5-bis (1-naphthyl) 1,3,4-thiadiazole, 1,4-bis [2- (5-phenylthiadiazolyl)] benzene, 3- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -4- Examples include phenyl-1,2,4-triazole, 3,5-bis (1-naphthyl) -4-m-tolyl-1,2,4-triazole, but are not limited thereto.
[0045]
In the organic EL device, in the light emitting layer, in addition to the compound represented by the general formula [1] or [2], at least one of a light emitting material, a doping material, a hole injection material, and an electron injection material is the same layer. May be contained. In order to improve the stability of the organic EL device obtained by the present invention with respect to temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. Is also possible.
[0046]
As a conductive material used for an anode of an organic EL element, a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, etc. Further, metal oxides such as tin oxide and indium oxide used for alloys thereof, ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used.
[0047]
As the conductive material used for the cathode, those having a work function smaller than 4 eV are suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, etc., and alloys thereof are used. However, it is not limited to these. Examples of alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. If necessary, the anode and the cathode may be formed of two or more layers.
[0048]
In the organic EL element, in order to efficiently emit light, it is desirable that at least one of the elements be sufficiently transparent in the light emission wavelength region of the element. The substrate is also preferably transparent. The transparent electrode is set using the above-described conductive material so as to ensure a predetermined translucency by a method such as vapor deposition or sputtering. The electrode on the light emitting surface preferably has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and has transparency. For example, a glass substrate, a polyethylene plate, a polyethylene terephthalate plate, a polyethersulfone plate, Examples thereof include a transparent resin such as a polypropylene plate.
[0049]
Each organic compound thin film of the organic EL device according to the present invention can be formed by any of dry deposition methods such as vacuum deposition, sputtering, plasma, and ion plating, and wet deposition methods such as spin coating, dipping, and flow coating. Can be applied. The film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The normal film thickness is suitably in the range of 5 nm to 10 μm, but more preferably in the range of 10 nm to 0.2 μm.
[0050]
In the case of the wet film-forming method, the material for forming each organic compound thin film is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form the thin film, and any solvent may be used. . In any organic compound thin film, an appropriate resin or additive may be used for improving the film formability and preventing pinholes in the film. Usable resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose, and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.
[0051]
As described above, by using the compound of the present invention in the light emitting layer of the organic EL device, the organic EL device characteristics such as the light emission efficiency and the maximum light emission luminance can be improved. In addition, this element is extremely stable against heat and current, and can be used for light emission brightness that can be used practically at a low driving voltage, so that the degradation that has been a major problem until now is greatly reduced. I was able to.
[0052]
The organic EL device of the present invention can be applied to flat panel displays such as wall-mounted TVs, flat light emitters, light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights. The industrial value is very large.
[0053]
The material of the present invention can also be used in the fields of organic EL devices, electrophotographic photoreceptors, photoelectric conversion devices, solar cells, image sensors and the like.
[0054]
【Example】
Hereinafter, the present invention will be described in more detail based on examples.
[0055]
Method for synthesizing compound (4)
5 parts of 1,4-naphthoquinone was dissolved in 50 parts of acetic acid, a mixed solution of 30 parts of concentrated sulfuric acid and 35 parts of acetic acid was added, and the mixture was heated and stirred for 50 hours. Thereafter, it was diluted with 500 parts of water. Extraction with ethyl acetate, concentration, and purification by column chromatography using silica gel gave 3 parts of a powder having white fluorescence. It was confirmed to be the compound (4) by molecular weight analysis using FD-MS.
[0056]
Examples using the compounds of the present invention are shown below. In this example, the characteristics of an organic EL element having an electrode area of 2 mm × 2 mm were measured.
[0057]
Example 1
On the washed glass plate with an ITO electrode, the compound (3) in Table 1 as a luminescent material, 2,5-bis (1-naphthyl) -1,3,4-oxadiazole, polycarbonate resin (Teijin Chemicals: Panlite) K-1300) was dissolved in tetrahydrofuran at a weight ratio of 5: 3: 2, and a light emitting layer having a thickness of 100 nm was obtained by a spin coating method. On top of that, an electrode having a thickness of 150 nm was formed from an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL element. The light emission characteristic of this element is 80 (cd / m at a DC voltage of 5V.2), Maximum brightness 1300 (cd / m)2), A light emission efficiency of 0.50 (lm / W) was obtained.
[0058]
Example 2
N, N′-di (3-methylphenyl) -N, N′-diphenyl-1,1-biphenyl-4,4-diamine (TPD) was vacuum-deposited on the cleaned glass plate with an ITO electrode, A hole injection layer having a thickness of 20 nm was obtained. Subsequently, the compound (2) was vapor-deposited to prepare a light-emitting layer having a thickness of 40 nm, and tris (8-hydroxyquinolinato) aluminum complex (Alq3) was vapor-deposited to obtain an electron injection layer having a thickness of 30 nm. On top of that, an electrode having a thickness of 100 nm was formed from an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL element. The hole injection layer and the light emitting layer are 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This device has a direct-current voltage of 5 V and an emission luminance of 100 (cd / m2), Maximum light emission luminance of 7000 (cd / m)2) Blue light emission with a luminous efficiency of 1.0 (lm / W) at 5 V was obtained.
[0059]
Example 3
Compound (7) was dissolved in methylene chloride on the washed glass plate with the ITO electrode, and a 50 nm-thick hole injection type light emitting layer was obtained by spin coating. Next, a bis (2-methyl-8-hydroxyquinolinate) (1-naphtholate) gallium complex is vacuum-deposited to form an electron injection layer having a thickness of 10 nm, on which magnesium and silver are added at a ratio of 10: 1. An electrode having a thickness of 100 nm was formed from the mixed alloy to obtain an organic EL device. The light emitting layer and the electron injection layer are 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This element is 150 (cd / m) at a DC voltage of 5V.2 ), Maximum brightness 10,000 (cd / m)2), Blue-green light emission with a luminous efficiency of 0.80 (lm / W) was obtained.
[0060]
Example 4
Compound (3) was vacuum-deposited on the washed glass plate with an ITO electrode to obtain a 50 nm-thick hole injection type light emitting layer. Next, a bis (2-methyl-8-hydroxyquinolinate) (1-naphtholate) gallium complex is vacuum-deposited to form an electron injection layer having a thickness of 10 nm, on which magnesium and silver are added at a ratio of 10: 1. An electrode having a thickness of 100 nm was formed from the mixed alloy to obtain an organic EL device. The light emitting layer and the electron injection layer are 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This element is 200 (cd / m) at a DC voltage of 5V.2), Maximum brightness 10,000 (cd / m)2), Emission with a luminous efficiency of 1.10 (lm / W) was obtained.
[0061]
Examples 5-15
4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (α-NPD) is vacuum-deposited on the cleaned glass plate with an ITO electrode to form a hole injection layer having a thickness of 20 nm. Formed. Subsequently, the compound of Table 2 was vacuum-deposited as a luminescent material, and the light emitting layer with a film thickness of 20 nm was obtained. Next, a bis (2-methyl-8-hydroxyquinolinate) (1-naphtholate) gallium complex is vacuum-deposited to form an electron injection layer having a thickness of 10 nm, on which magnesium and silver are added at a ratio of 10: 1. An electrode having a thickness of 100 nm was formed from the mixed alloy to obtain an organic EL device. The hole injection layer and the light emitting layer are 10-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. The light emission characteristics of this element are shown in Table 2. The light emission luminance here is the luminance when a DC voltage of 5 V is applied. The organic EL elements of this example all have a maximum luminance of 10,000 (cd / m2) High luminance characteristics as described above, and a blue to green emission color was obtained.
[0062]
[Table 2]
Example 16
4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine is vacuum-deposited on a cleaned glass plate with an ITO electrode to inject holes with a thickness of 40 nm. Next, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (α-NPD) was vacuum-deposited to form a second hole injection layer having a thickness of 10 nm. Further, the compound (1) was vacuum-deposited to prepare a light-emitting layer having a film thickness of 30 nm, and further a bis (2-methyl-8-hydroxyquinolinato) (1-phenolate) gallium complex was vacuum-deposited. An electron injection layer having a thickness of 30 nm was prepared, and an electrode having a thickness of 150 nm was formed from an alloy in which aluminum and lithium were mixed at a ratio of 25: 1, thereby obtaining an organic EL device. 10 layers-6Deposition was performed in a vacuum of Torr at a substrate temperature of room temperature. This device has a luminance of 410 (cd / m) at a DC voltage of 5V.2), Maximum luminous brightness 18000 (cd / m)2), Blue light emission with a luminous efficiency of 1.8 (lm / W) was obtained.
[0064]
Example 17
Except for providing a 5 nm thick hole injection layer of metal-free phthalocyanine between the ITO electrode and 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (α-NPD). An organic EL device was produced in the same manner as in Example 3. This element is 800 (cd / m) at a DC voltage of 5V.2), Maximum brightness 13000 (cd / m)2), Blue-green light emission with a luminous efficiency of 1.00 (lm / W) was obtained.
[0065]
Example 18
Example 16 except that a 20 nm thick hole injection layer of metal-free phthalocyanine is provided in place of 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine An organic EL element was manufactured in the same manner as in Example 1. This element was 250 (cd / m) at a DC voltage of 5 V.2), Maximum brightness 15000 (cd / m)2), Blue-green light emission with a luminous efficiency of 1.50 (lm / W) was obtained.
[0066]
Example 19
An organic EL device was produced in the same manner as in Example 16 except that a 10 nm-thick hole injection layer in which compound (3): compound (4) was deposited at a ratio of 1: 5 was provided as the light-emitting layer. This element is 900 (cd / m) at a DC voltage of 5V.2), Maximum brightness 18000 (cd / m)2), Blue-green light emission with a luminous efficiency of 1.80 (lm / W) was obtained.
[0067]
Example 20
The present invention was carried out except that a 10 nm-thick hole injection layer in which a compound (3): bis (2-methyl-8-hydroxyquinolinate) (phenolate) gallium complex was deposited at a ratio of 1: 100 was provided as the light emitting layer. An organic EL device was produced in the same manner as in Example 16. This element has a DC voltage of 5 V and 260 (cd / m2), Maximum brightness 20000 (cd / m)2), Blue light emission with a luminous efficiency of 1.90 (lm / W) was obtained.
[0068]
The organic EL element shown in this example has a maximum emission luminance of 10,000 (cd / m) in a two-layer or higher element configuration.2) The above luminescence was obtained and high luminous efficiency could be obtained. For the organic EL element shown in this example, 3 (mA / cm2), Stable emission was observed for 1000 hours or more.
The organic EL device of the present invention achieves improvement in light emission efficiency, light emission luminance and long life, and is used together with light emitting materials, doping materials, hole injection materials, electron injection materials, sensitizers, resins. The electrode material and the element manufacturing method are not limited.
[0069]
【The invention's effect】
The organic EL element using the light emitting material for organic EL of the present invention as a light emitting material showed high luminance and higher luminance than conventional ones, and a long-life organic EL element could be obtained.
Claims (4)
一般式［１］
General formula [1]
一般式［２］
General formula [2]
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| CN1745050A (en) * | 2003-01-31 | 2006-03-08 | 株式会社日本触媒 | Tricyclopenta-triphenylene and preparing method thereof |
| JP4822687B2 (en) | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | Organic electroluminescence device |
| JP4883955B2 (en) * | 2004-07-30 | 2012-02-22 | 国立大学法人大阪大学 | Organic semiconductor and electronic device using the same |
| JP4604236B2 (en) * | 2004-07-30 | 2011-01-05 | 国立大学法人大阪大学 | Molecular assembly |
| JP5753027B2 (en) | 2011-08-22 | 2015-07-22 | ユー・ディー・シー アイルランド リミテッド | ORGANIC ELECTROLUMINESCENT ELEMENT, COMPOUND, AND LIGHT EMITTING DEVICE, DISPLAY DEVICE AND LIGHTING DEVICE USING THE ELEMENT |
| CN107880056B (en) * | 2016-09-30 | 2020-07-14 | 南京高光半导体材料有限公司 | Organic electroluminescent compounds and organic electroluminescent device using the same |
| US10608185B2 (en) | 2016-10-17 | 2020-03-31 | Univeral Display Corporation | Organic electroluminescent materials and devices |
| JP2022521417A (en) * | 2019-02-25 | 2022-04-07 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Organic electroluminescent compounds and organic electroluminescent devices containing them |
| KR102463816B1 (en) * | 2019-09-27 | 2022-11-04 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| CN114907361B (en) * | 2022-06-03 | 2024-06-04 | 北京八亿时空液晶科技股份有限公司 | Trimeric heterocyclic derivative and application thereof |
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