JP3564859B2 - 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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- JP3564859B2 JP3564859B2 JP07850196A JP7850196A JP3564859B2 JP 3564859 B2 JP3564859 B2 JP 3564859B2 JP 07850196 A JP07850196 A JP 07850196A JP 7850196 A JP7850196 A JP 7850196A JP 3564859 B2 JP3564859 B2 JP 3564859B2
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- 239000000463 material Substances 0.000 title claims description 72
- 238000005401 electroluminescence Methods 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 29
- -1 metal complex compound Chemical class 0.000 claims description 27
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- MKZHJJQCUIZEDE-UHFFFAOYSA-N 1-[(2-hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)COC=3C4=CC=CC=C4C=CC=3)C(C)C)=CC=CC2=C1 MKZHJJQCUIZEDE-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
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- 230000000996 additive effect Effects 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
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- 150000003141 primary amines Chemical group 0.000 description 1
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- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 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
- RPVGLMKJGQMQSN-UHFFFAOYSA-N tiliquinol Chemical compound C1=CC=C2C(C)=CC=C(O)C2=N1 RPVGLMKJGQMQSN-UHFFFAOYSA-N 0.000 description 1
- 229950005513 tiliquinol Drugs 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
- 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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Description
【０００１】
【発明の技術分野】
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、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］で示される有機ＥＬ素子用材料を少なくとも一層に使用した有機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用材料に関する。
一般式［１］
【０００７】
【化５】
［式中、Ａは、置換もしくは未置換の炭素原子数１０〜２０の縮合アリーレン基を表し、Ｘ1〜Ｘ4は、それぞれ独立に、置換もしくは未置換の炭素原子数６〜２０のアリーレン基を表す。Ｙ1〜Ｙ4は、それぞれ独立に、下記一般式［２］で示される有機基を表す。
一般式［２］
【０００９】
【化６】
（式中、Ｒ1 〜Ｒ4 は、水素原子、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リール基、シアノ基を表すか、Ｒ1 とＲ2 またはＲ3 とＲ4 が結合した三重結合を表す。Ｚは、置換もしくは未置換のアリール基を表す。ａ〜ｄは、０〜２の正の整数を表す。ただし、ａ〜ｄのいずれかは１以上である。ｎは、０もしくは１を表す。）］
【００１２】
さらに本発明は、上記一般式［１］で示される有機エレクトロルミネッセンス素子用発光材料である。
【００１３】
さらに本発明は、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用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である。
【００１４】
さらに本発明は、芳香族三級アミン誘導体および／またはフタロシアニン誘導体を含有する層を、発光層と陽極との間に形成してなる上記有機エレクトロルミネッセンス素子である。
【００１５】
さらに本発明は、芳香族三級アミン誘導体が、下記一般式［３］で示される化合物である上記有機エレクトロルミネッセンス素子である。
一般式［３］
【化７】
【００１６】
さらに本発明は、金属錯体化合物もしくは含窒素五員環誘導体を含有する層を、発光層と陰極との間に形成してなる上記有機エレクトロルミネッセンス素子である。
【００１７】
さらに本発明は、金属錯体化合物が、下記一般式［４］で示される化合物である上記有機エレクトロルミネッセンス素子である。
一般式［４］
【化８】
【発明の実施の形態】
【００１８】
本発明における一般式［１］で示される化合物のＡは、置換もしくは未置換の炭素原子数１０〜２０の縮合アリーレン基を表し、Ｘ1〜Ｘ4は、それぞれ独立に置換もしくは未置換の炭素原子数６〜２０のアリーレン基を表す。これらの具体例は、フェニレン基、ビフェニレン基、ターフェニレン基、ナフチレン基、アントリレン基、フェナントリレン基、フルオレニレン基、ピレニレン基、チオフェニレン基等のアリーレン基および下記一般式［５］もしくは一般式［６］で示されるアリーレン基であるがこれらに限定されるものではない。また、炭素原子数１０〜２０の縮合アリーレン基は、ナフチレン基、アントリレン基、フェナントリレン基、フルオレニレン基、ピレニレン基のように炭素原子数１０〜２０からなる二価の縮合芳香族環を表す。
【００１９】
一般式［５］
【化９】
一般式［６］
【化１０】
ここで、一般式［５］および一般式［６］のＡｒ１ 〜Ａｒ４ は、それぞれ独立に置換もしくは未置換の炭素原子数６〜２０のアリーレン基を表す。Ａｒ１ 〜Ａｒ ４の具体例は、フェニレン基、ビフェニレン基、ターフェニレン基、ナフチレン基、アントリレン基、フェナントリレン基、フルオレニレン基、ピレニレン基、チオフェニレン基等のアリーレン基である。Ｄ１ 〜Ｄ３ は、直接結合または、Ｃ、Ｎ、Ｈ、Ｏ、Ｓから選ばれる１〜５０個の原子で構成される化学的に合理的な組合わせからなる二価の結合基である。
【００２２】
本発明における一般式［２］で示される化合物のＲ1 〜Ｒ4 は、それぞれ独立に、水素原子、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リール基もしくはシアノ基を表す。
Ｒ1 〜Ｒ4 の具体例は、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がある。
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、ピレニル基等がある。
一般式［１］において、ａ〜ｄはそれぞれ独立に０〜２の正の整数を表し、ただし、ａ〜ｄのいずれかは１以上である。ｎはそれぞれ独立に０もしくは１を表す。
【００２３】
本発明における一般式［２］で示される化合物のＺは、それぞれ独立に置換もしくは未置換の炭素原子数６〜２０のアリール基を表す。Ｚの具体例は、フェニル基、ビフェニル基、ターフェニル基、ナフチル基、アントリル基、フェナントリル基、フルオレニル基、ピレニル基、チオフェン基等のアリール基であり、上記アリール基は置換基を有していても良い。置換基の具体例は、Ｒ１ 〜Ｒ４ で記述したアルキル基およびアリール基に加えて、アルコキシ基、アミノ基、シアノ基、水酸基、カルボン酸基、エーテル基、エステル基等がある。
【００２４】
以下に、本発明の一般式［１］の化合物の代表例を、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。
【００２５】
表１
【００２６】
本発明における一般式［３］で示される化合物のＢ１ 〜Ｂ４ の具体例は、置換もしくは未置換の炭素原子数６〜２０のアリール基である。具体的には、フェニル基、ビフェニル基、ターフェニル基、ナフチル基、アントリル基、フェナントリル基、フルオレニル基、ピレニル基等の窒素原子を含有しても良いアリール基であり、それぞれのアリール基は置換基を有していても良い。Ｇは、二価のアリーレン基であり、フェニレン基、ビフェニレン基、ターフェニレン基、ナフチレン基、アントリレン基、フェナントリレン基、フルオレニレン基、ピレニレン基等の窒素原子を含有しても良い二価のアリーレン基であり、それぞれのアリール基は置換基を有していても良い。
【００３８】
以下に、効果的な正孔注入材料である本発明の一般式［３］の化合物およびその他の材料の代表例を、表２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。
【００３９】
【表２】
本発明における一般式［４］で示される化合物のＱ１ 、Ｑ４ は、８−ヒドロキシキノリン、８−ヒドロキシキナルジン、８−ヒドロキシ−２−フェニルキノリン、８−ヒドロキシ−５−メチルキノリン、８−ヒドロキシ−３，５，７−トリフルオロキノリン等のヒドロキシキノリン誘導体、Ｌは、ハロゲン原子、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シクロアルキル基、置換もしくは未置換の窒素原子を含んでも良いアリール基、−ＯＲ（Ｒは水素原子、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シクロアルキル基、置換もしくは未置換の窒素原子を含んでも良いアリール基である。）、−Ｏ−Ｇａ−Ｑ３ （Ｑ４ ）（Ｑ３ およびＱ４ は、Ｑ１ およびＱ２ と同じ意味を表す。）を示す。ここで、ハロゲン原子、アルキル基、シクロアルキル基、窒素原子を含んでも良いアリール基、および−ＯＲ基のＲのアルキル基、シクロアルキル基、窒素原子を含んでも良いアリール基は、前記の一般式［２］で記述したＲ１ 〜Ｒ４ と同様の基を表す。
【００４４】
以下に、本発明の有機ＥＬ素子に使用する一般式［４］の化合物の代表例および電子注入材料の代表例を、表３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。
【００４５】
【表３】
本発明の一般式［１］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、金属電極もしくは有機薄膜層からの優れた正孔注入性および正孔輸送性、金属電極もしくは有機薄膜層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。
【００５２】
有機ＥＬ素子は、陽極と陰極間に一層もしくは多層の有機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／正孔注入層／発光層／陰極）、（陽極／発光層／電子注入層／陰極）、（陽極／正孔注入層／発光層／電子注入層／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することができる。
【００５３】
発光層には、必要があれば、本発明の一般式［１］の化合物に加えて、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、正孔注入層、発光層、電子注入層は、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、正孔注入層の場合、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、電子注入層の場合、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。
【００５４】
一般式［１］の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、ルブレンおよび蛍光色素等があるが、これらに限定されるものではない。
【００５５】
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層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、オキサゾール、オキサジアゾール、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。
【００５６】
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、一般式［３］で示した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。具体的には、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’−（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’−（４−メチルフェニル）−１，１’−フェニル−４，４’−ジアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−（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’−ジナフチル−１，１’−ビフェニル−４，４’−ジアミン、Ｎ，Ｎ’−（メチルフェニル）−Ｎ，Ｎ’−（４−ｎ−ブチルフェニル）−フェナントレン−９，１０−ジアミン、Ｎ，Ｎ−ビス（４−ジ−４−トリルアミノフェニル）−４−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。
【００５７】
フタロシアニン（Ｐｃ）誘導体としては、Ｈ２ Ｐｃ、ＣｕＰｃ、ＣｏＰｃ、ＮｉＰｃ、ＺｎＰｃ、ＰｄＰｃ、ＦｅＰｃ、ＭｎＰｃ、ＣｌＡｌＰｃ、ＣｌＧａＰｃ、ＣｌＩｎＰｃ、ＣｌＳｎＰｃ、Ｃｌ２ ＳｉＰｃ、（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。
【００５８】
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層への移動を防止し、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。
【００５９】
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−キノリナート）クロロガリウム、ビス（２−メチル−８−キノリナート）（ｏ−クレゾラート）ガリウム、ビス（２−メチル−８−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−キノリナート）（２−ナフトラート）ガリウム等があるが、これらに限定されるものではない。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、ジメチルＰＯＰＯＰ、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、２−（４’−ｔｅｒｔ−ブチルフェニル）−５−（ ４”−ビフェニル） −１，３，４−トリアゾール、２，５−ビス（１−ナフチル）−１，３，４−トリアゾール、１，４−ビス［２−（ ５−フェニルトリアゾリル） ］ベンゼン等があるが、これらに限定されるものではない。
【００６０】
本有機ＥＬ素子においては、発光層中に、一般式［１］の化合物の他に、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。
【００６１】
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。
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。
【００６２】
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、ガラス基板および透明性樹脂フィルムがある。透明性樹脂フィルムとしては、ポリエチレン、エチレン−酢酸ビニル共重合物、エチレン−ビニルアルコール共重合物、ポリプロピレン、ポリスチレン、ポリメチルメタアクリレート、ポリ塩化ビニル、ポリビニルアルコール、ポリビニルブチラール、ナイロン、ポリエーテルエーテルケトン、ポリサルホン、ポリエーテルサルフォン、テトラフルオロエチレン−パーフルオロアルキルビニルエーテル、ポリビニルフルオライド、テトラフルオロエチレン−エチレン、テトラフルオロエチレン−ヘキサフルオロプロピレン、ポリクロロトリフルオロエチレン、ポリビニリデンフルオライド、ポリエステル、ポリカーボネート、ポリウレタン、ポリイミド、ポリエーテルイミド、ポリイミド、ポリプロピレン等があげられる。
【００６３】
本発明に係わる有機ＥＬ素子の各層の形成は、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。
【００６４】
湿式成膜法の場合、各層を形成する材料を、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、いずれの有機薄膜層においても、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。
【００６５】
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、更には特定の正孔注入層もしくは電子注入層と組み合わせることにより、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。
【００６６】
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。
【００６７】
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。
【００６８】
【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。
【００６９】
実施例２
洗浄したＩＴＯ電極付きガラス板上に、表１の化合物（８）を真空蒸着して膜厚１００ｎｍの発光層を作成し、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１１０（ｃｄ／ｍ２ ）、最高輝度２２００（ｃｄ／ｍ２ ）、発光効率０．７５（ｌｍ／Ｗ）の発光が得られた。
【００７０】
実施例３
洗浄したＩＴＯ電極付きガラス板上に、表１の化合物（１２）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の発光層を得た。次いで、表３の化合物（Ｂ−１０）を真空蒸着して膜厚３０ｎｍ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３５０（ｃｄ／ｍ２ ）、最高輝度５４００（ｃｄ／ｍ２ ）、発光効率１．３（ｌｍ／Ｗ）の緑色発光が得られた。
【００７１】
実施例４
洗浄したＩＴＯ電極付きガラス板上に、表１の化合物（１６）を真空蒸着して、膜厚５０ｎｍに発光層を形成した。次いで、表３の化合物（Ｂ−３）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。この素子は、直流電圧５Ｖで約４１０（ｃｄ／ｍ２ ）、最高輝度１００００（ｃｄ／ｍ２ ）、発光効率１．６（ｌｍ／Ｗ）の緑色発光が得られた。
【００７２】
実施例５〜５１
洗浄したＩＴＯ電極付きガラス板上に、表４の条件で、正孔注入材料を真空蒸着して、膜厚３０ｎｍの正孔注入層を得た。次いで、発光材料を真空蒸着して膜厚３０ｎｍの発光層を得た。さらに、電子注入材料を真空蒸着して膜厚３０ｎｍ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１５０ｎｍの膜厚の電極を形成して有機ＥＬ素子を得た。各層は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４に示す。ここでの発光輝度は、直流電圧５Ｖ印可時の輝度であり、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ていた。有機ＥＬ素子の素子構成としては、一般式の発光材料に、一般式［３］の正孔注入材料および一般式［４］の電子注入材料を組み合わせた素子が、最も良好な特性を示した。
【００７３】
【表４】
実施例５２
洗浄したＩＴＯ電極付きガラス板上に、正孔注入材料（Ａ−１３）を真空蒸着して、膜厚４０ｎｍの正孔注入層を得た。次いで、発光材料として化合物（８）を真空蒸着して膜厚４０ｎｍの発光層を得た。さらに、電子注入材料として（Ｂ−１１）を真空蒸着して、膜厚３０ｎｍの電子注入層を得た。その上に、アルミニウム：リチウムを５０：１の比率の合金で膜厚１５０ｎｍの電極を形成して有機ＥＬ素子を得た。この素子は、直流電圧５Ｖで８０００（ｃｄ／ｍ２ ）、最高輝度１３１０００（ｃｄ／ｍ２ ）、発光効率１３．８（ｌｍ／Ｗ）の発光が得られた。
【００７５】
実施例５３
ＩＴＯ電極と化合物（Ａ−１３）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５２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１００００（ｃｄ／ｍ２ ）、最高輝度９９０００（ｃｄ／ｍ２ ）、発光効率１０．２（ｌｍ／Ｗ）の発光が得られた。
【００７６】
実施例５４
化合物（Ａ−１３）の代わりに無金属フタロシアニンの膜厚１５ｎｍの正孔注入層を設ける以外は、実施例４８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３５００（ｃｄ／ｍ２ ）、最高輝度７７０００（ｃｄ／ｍ２ ）、発光効率５．８（ｌｍ／Ｗ）の発光が得られた。
【００７７】
実施例５５〜６４
発光層として、化合物（８）と表５で示した化合物を１００：１の重量比で蒸着した膜厚２０ｎｍの発光層を使用する以外は、実施例５２と同様の方法で有機ＥＬ素子を作製した。この素子の発光特性を表６に示す。ここでの発光輝度は、直流電圧５Ｖ印可時の輝度であり、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、目的の発光色を得ることができた。
【００７８】
【表５】
【表６】
本実施例で示された有機ＥＬ素子は、発光輝度として１００００（ｃｄ／ｍ２ ）以上であり、全て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、ダークスポットもほとんど観察されなかった。本発明の有機ＥＬ素子材料を使用した有機ＥＬ素子は、発光材料の蛍光量子効率が極めて高いので、この発光材料を使用した素子においては、低電流印可領域での高輝度発光が可能になり、また、発光層中で一般式［１］の化合物に加えてドーピング材料を使用することにより、最大発光輝度、最大発光効率を向上できた。さらには、青緑色、緑色および黄色の発光をする一般式［１］の化合物に、赤色発光もしくは青色発光のドーピング材料を添加することによって、赤色発光もしくは青色発光の発光素子を得ることができた。
【００８２】
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。
【００８３】
【発明の効果】
本発明の有機ＥＬ素子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。以上により本発明で示した化合物を、有機ＥＬ素子の少なくとも一層に使用すること、および、本発明の素子構成により形成された有機ＥＬ素子は、高輝度、高発光効率、長寿命の有機ＥＬ素子を容易に作製することが可能となった。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a light emitting material for an organic electroluminescence (EL) element used for a flat light source and a display, and a high-luminance light emitting element.
[0002]
[Prior art]
2. Description of the Related Art An EL element using an organic substance is expected to be used as a solid-state light-emitting inexpensive large-area full-color display element, and many developments have been made. Generally ELelementIs composed of a light emitting layer and a pair of opposed 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.,This is a phenomenon in which the electrons recombine with holes in the light emitting layer, and emit energy as light when the energy level returns from the conduction band to the valence band.
[0003]
The conventional organic EL element has a higher driving voltage and lower light emission luminance and light emission efficiency than the inorganic EL element. In addition, the characteristics deteriorated remarkably, and practical use has not been achieved.
In recent years, an organic EL device formed by laminating a thin film containing an organic compound having a high fluorescence quantum efficiency and emitting light at a low voltage of 10 V or less has been reported and attracted attention (Applied Physics Letters, vol. 51, p. 913). 1987).
This method uses a metal chelate complex for a light emitting layer and an amine compound for a hole injection layer to obtain high-luminance green light emission, and a luminance of several 1000 cd / m at a DC voltage of 6 to 7 V.2And a maximum luminous efficiency of 1.5 lm / W, which is close to the practical range.
[0004]
However, organic EL devices up to now have improved light emission intensity due to the improved structure, but do not yet have sufficient light emission luminance. In addition, there is a major problem that the stability upon repeated use is poor. This is because, for example, a metal chelate complex such as a tris (8-hydroxyquinolinato) aluminum complex is chemically unstable during electroluminescence, has poor adhesion to a cathode, and is greatly deteriorated by short-time light emission. I was For the above reasons, in order to develop an organic EL device having high luminous luminance and luminous efficiency and having excellent stability in repeated use, development of a durable luminescent material having excellent luminous ability has been required. 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 when used repeatedly. As a result of intensive studies by the present inventors, it has been found that an organic EL device using the material for an organic EL device represented by the general formula [1] in at least one layer has high light emission luminance and light emission efficiency, and also has excellent stability during repeated use. And found that the present invention was achieved.
[0006]
[Means for Solving the Problems]
The present invention relates to a material for an organic electroluminescence device represented by the following general formula [1].
General formula [1]
[0007]
Embedded image
[Where ARepresents a substituted or unsubstituted fused arylene group having 10 to 20 carbon atoms,X1~ XFourEach independently represents a substituted or unsubstituted arylene group having 6 to 20 carbon atoms. Y1~ YFourEach independently represents an organic group represented by the following general formula [2].
General formula [2]
[0009]
Embedded image
(Where R1~ RFourRepresents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a cyano group;1And RTwoOr RThreeAnd RFourRepresents a triple bond bonded. Z represents a substituted or unsubstituted aryl group. a to d represent positive integers of 0 to 2.However, any of ad is 1 or more.n represents 0 or 1. )]
[0012]
Further, the present invention is a light emitting material for an organic electroluminescent device represented by the above general formula [1].
[0013]
Furthermore, the present invention provides an organic electroluminescence 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 at least one layer contains the above-mentioned material for an organic electroluminescence device. It is an organic electroluminescence element.
[0014]
Furthermore, the present invention is the above-mentioned organic electroluminescence device, wherein a layer containing an aromatic tertiary amine derivative and / or a phthalocyanine derivative is formed between a light emitting layer and an anode.
[0015]
Furthermore, the present invention is the above-mentioned organic electroluminescence device, wherein the aromatic tertiary amine derivative is a compound represented by the following general formula [3].
General formula [3]
Embedded image
[0016]
Furthermore, the present invention is the above-described organic electroluminescence device, wherein a layer containing a metal complex compound or a nitrogen-containing five-membered ring derivative is formed between the light-emitting layer and the cathode.
[0017]
Further, the present invention is the above-mentioned organic electroluminescence device, wherein the metal complex compound is a compound represented by the following general formula [4].
General formula [4]
Embedded image
BEST MODE FOR CARRYING OUT THE INVENTION
[0018]
A of the compound represented by the general formula [1] in the present inventionRepresents a substituted or unsubstituted fused arylene group having 10 to 20 carbon atoms,X1~ XFourEach independently represents a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.theseAre arylene groups such as a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a fluorenylene group, a pyrenylene group, a thiophenylene group, and the following general formula [5] or general formula [6]. However, the present invention is not limited thereto. The fused arylene group having 10 to 20 carbon atoms represents a divalent fused aromatic ring having 10 to 20 carbon atoms such as a naphthylene group, an anthrylene group, a phenanthrylene group, a fluorenylene group, and a pyrenylene group.
[0019]
General formula [5]
Embedded image
General formula [6]
Embedded image
Here, Ar of the general formula [5] and the general formula [6]1~ Ar4Each independently represents a substituted or unsubstituted arylene group having 6 to 20 carbon atoms. Ar1~ Ar4Are arylene groups such as phenylene group, biphenylene group, terphenylene group, naphthylene group, anthrylene group, phenanthrylene group, fluorenylene group, pyrenylene group and thiophenylene group. D1~ D3Is a direct bond or a divalent linking group consisting of a chemically rational combination of 1 to 50 atoms selected from C, N, H, O and S.
[0022]
R of the compound represented by the general formula [2] in the present invention1~ RFourEach independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a cyano group.
R1~ RFourSpecific examples of the substituted or unsubstituted alkyl group include methyl, ethyl, propyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and stearyl. Group, 2-phenylisopropyl group, trichloromethyl group, trifluoromethyl group, benzyl group, α-phenoxybenzyl group, α, α-dimethylbenzyl group, α, α-methylphenylbenzyl group, α, α-ditrifluoromethyl A benzyl group, a triphenylmethyl group, an α-benzyloxybenzyl group and the like.
Examples of the substituted or unsubstituted aryl group include phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-ethylphenyl, biphenyl, 4-methylbiphenyl, and 4-ethylbiphenyl Group, 4-cyclohexylbiphenyl group, terphenyl group, 3,5-dichlorophenyl group, naphthyl group, 5-methylnaphthyl group, anthryl group, pyrenyl group and the like.
In the general formula [1], a to d each independently represent a positive integer of 0 to 2,However, any of ad is 1 or more.n represents 0 or 1 each independently.
[0023]
Z of the compound represented by the general formula [2] in the present invention independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. Specific examples of Z include an aryl group such as a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, and a thiophene group, and the aryl group has a substituent. May be. Specific examples of the substituent include R1~ R4In addition to the alkyl and aryl groups described in the above, there are an alkoxy group, an amino group, a cyano group, a hydroxyl group, a carboxylic acid group, an ether group, an ester group and the like.
[0024]
Hereinafter, typical examples of the compound of the general formula [1] of the present invention are specifically shown in Table 1, but the present invention is not limited to these typical examples.
[0025]
Table 1
[0026]
B of the compound represented by the general formula [3] in the present invention1~ B4Is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. Specifically, an aryl group which may contain a nitrogen atom such as a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, and the like. It may have a group. G is a divalent arylene group, which may contain a nitrogen atom such as a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a fluorenylene group, and a pyrenylene group. And each aryl group may have a substituent.
[0038]
In the following, typical examples of the compound of the general formula [3] of the present invention and other materials which are effective hole injection materials are specifically illustrated in Table 2, but the present invention is limited to these typical examples. It is not done.
[0039]
[Table 2]
Q of the compound represented by the general formula [4] in the present invention1, Q4Is a hydroxyquinoline derivative such as 8-hydroxyquinoline, 8-hydroxyquinaldine, 8-hydroxy-2-phenylquinoline, 8-hydroxy-5-methylquinoline, 8-hydroxy-3,5,7-trifluoroquinoline, L is a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, an aryl group which may contain a substituted or unsubstituted nitrogen atom, -OR (R is a hydrogen atom, a substituted or unsubstituted An alkyl group, a substituted or unsubstituted cycloalkyl group, or an aryl group which may contain a substituted or unsubstituted nitrogen atom.), -O-Ga-Q3(Q4) (Q3And Q4Is Q1And Q2Has the same meaning as ). Here, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group that may contain a nitrogen atom, and an alkyl group of R of the —OR group, a cycloalkyl group, and an aryl group that may contain a nitrogen atom are represented by the general formula described above. R described in [2]1~ R4Represents the same group as
[0044]
Hereinafter, typical examples of the compound of the general formula [4] and typical examples of the electron injecting material used in the organic EL device of the present invention are specifically shown in Table 3, but the present invention is limited to these typical examples. It is not done.
[0045]
[Table 3]
The compound represented by the general formula [1] of the present invention has strong fluorescence in a solid state and is excellent in electroluminescence. In addition, it has excellent hole injection and hole transport properties from the metal electrode or organic thin film layer, and excellent electron injection and electron transport properties from the metal electrode or organic thin film layer. It can be used effectively, and even if other hole transporting materials, electron transporting materials or doping materials can be used.
[0052]
An organic EL device is a device in which a single or multilayer organic thin film is formed between an anode and a cathode. In the case of a 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-injection material or an electron-injection material for transporting holes injected from an anode or electrons injected from a cathode to the light-emitting material. However, since the light emitting material of the present invention has extremely high light emission quantum efficiency, high hole transporting ability and electron transporting ability and can form a uniform thin film, a light emitting layer is formed only with the light emitting material of the present invention. It is also possible. The multilayer type includes (anode / hole injection layer / emission layer / cathode), (anode / emission layer / electron injection layer / cathode), and (anode / hole injection layer / emission layer / electron injection layer / cathode) There is an organic EL element stacked in a configuration. The compound represented by the general formula [1] has high light-emitting properties, and has a hole-injecting property, a hole-transporting property, an electron-injecting property, and an electron-transporting property.
[0053]
In the light emitting layer, if necessary, in addition to the compound of the general formula [1] of the present invention, further known light emitting materials, doping materials, hole injection materials and electron injection materials can be used. When the organic EL element has a multilayer structure, it is possible to prevent a decrease in luminance and life due to quenching. If necessary, a combination of a light emitting material, a doping material, a hole injection material, and an electron injection material can be used. Further, with the use of the doping material, emission luminance and emission efficiency can be improved, and red and blue light emission can be obtained. Further, each of the hole injection layer, the light emitting layer, and the electron injection layer may be formed with two or more layers. In this case, in the case of a hole injection layer, a layer for injecting holes from the electrode is a hole injection layer, and a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer is a hole transport layer. Call. Similarly, in the case of an electron injection layer, a layer that injects electrons from the electrode is called an electron injection layer, and a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer is called an electron transport layer. These layers are selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or the metal electrode.
[0054]
Examples of the light-emitting material or the doping material that can be used in the light-emitting layer together with the compound of the general formula [1] include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenyl Butadiene, 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 chelated oxinoid compounds, quinacridone, rubre And there is a fluorescent dye or the like, but is not limited thereto.
[0055]
As a hole injecting material, it has the ability to transport holes, has a hole injecting effect from the anode, an excellent hole injecting effect on the light emitting layer or the light emitting material, and has a function of excitons generated in the light emitting layer. A compound that prevents migration to an electron injection layer or an electron injection material and has excellent thin film forming ability can be used. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyaryl There are alkanes, stilbenes, butadienes, benzidine-type triphenylamines, styrylamine-type triphenylamines, diamine-type triphenylamines and the like, and derivatives thereof, and polymer materials such as polyvinylcarbazole, polysilane, and conductive polymers. However, the present invention is not limited to these.
[0056]
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 represented by the general formula [3]. Specifically, triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N, N ', N'-(4-methylphenyl) -1,1'-phenyl-4,4'-diamine, N, N, N ', N'-(4-methylphenyl) -1,1 ' -Biphenyl-4,4'-diamine, N, N'-diphenyl-N, N'-dinaphthyl-1,1'-biphenyl-4,4'-diamine, N, N '-(methylphenyl) -N, N '-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane, and the like, Oligomers with Primary Amine Skeleton Or is a polymer such as, but not limited thereto.
[0057]
As phthalocyanine (Pc) derivatives, H2Pc, CuPc, CoPc, 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, GaPc-O-GaPc, and naphthalocyanine derivatives.
[0058]
As an electron injection material, it has the ability to transport electrons, has the effect of injecting holes from the cathode, has an excellent electron injection effect on the light emitting layer or the light emitting material, and injects excitons generated in the light emitting layer. Compounds that prevent migration to a layer and have an excellent ability to form a thin film may be mentioned. For example, there are fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone, and derivatives thereof. However, the present invention is not limited to these. Alternatively, the electron injecting material may be sensitized by adding an electron accepting substance to the hole injecting material and the electron donating substance to the electron injecting material.
[0059]
In the organic EL device of the present invention, a more effective electron injecting material is a metal complex compound or a nitrogen-containing five-membered ring derivative. Specifically, as the metal complex compound, lithium 8-hydroxyquinolinato, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) 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-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolate) gallium, bis (2-methyl- 8-quinolinato) (1-naphtholate) aluminum, bis (2-meth There is Le-8-quinolinate) (2-naphtholato) gallium and the like, but is not limited thereto. 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, dimethyl POPOP, 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-phenyloxa Diazolyl) -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, 2- (4'-tert-butylphenyl) -5- (4 "-biphenyl) -1,3,4-triazole, 2,5 -Bis (1-naphthyl) -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)] benzene and the like, but are not limited thereto.
[0060]
In the present organic EL device, in the light emitting layer, at least one of a light emitting material, a doping material, a hole injection material, and an electron injection material may be contained in the same layer in addition to the compound of the general formula [1]. . In order to improve the stability of the organic EL device obtained according to the present invention with respect to temperature, humidity, atmosphere, and the like, a protective layer may be provided on the surface of the device, or the entire device may be protected with silicon oil, resin, or the like. Is also possible.
[0061]
As the conductive material used for the anode of the organic EL element, those having a work function of more than 4 eV are suitable, such as carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, and palladium. And alloys thereof, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole.
As the conductive substance 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, the present invention is not limited to these. Representative examples of the alloy 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, atmosphere, degree of vacuum, and the like of the evaporation source, and is selected to be an appropriate ratio. The anode and the cathode may be formed of two or more layers if necessary.
[0062]
In an organic EL device, it is desirable that at least one of the organic EL devices is sufficiently transparent in an emission wavelength region of the device in order to emit light efficiently. Further, it is desirable that the substrate is also transparent. The transparent electrode is set using the above-described conductive material so as to secure a predetermined translucency by a method such as vapor deposition or sputtering. It is desirable that the electrode on the light emitting surface has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strengths and is transparent, and includes a glass substrate and a transparent resin film. As the transparent resin film, polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone , Polysulfone, polyethersulfone, tetrafluoroethylene-perfluoroalkyl vinyl ether, polyvinyl fluoride, tetrafluoroethylene-ethylene, tetrafluoroethylene-hexafluoropropylene, polychlorotrifluoroethylene, polyvinylidene fluoride, polyester, polycarbonate, Examples include polyurethane, polyimide, polyetherimide, polyimide, and polypropylene.
[0063]
The formation of each layer of the organic EL device according to the present invention employs any of dry film forming methods such as vacuum deposition, sputtering, plasma, and ion plating, and wet film forming methods such as spin coating, dipping, and flow coating. be able to. The film thickness is not particularly limited, but needs to be set to an appropriate film thickness. When the film thickness is too large, a large applied voltage is required to obtain a constant light output, and the efficiency is deteriorated. If the film thickness is too small, pinholes or 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 is more preferably in the range of 10 nm to 0.2 μm.
[0064]
In the case of the wet film formation method, a material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used. In any of the organic thin film layers, an appropriate resin or additive may be used for improving film forming properties and preventing pinholes in the film. Examples of usable resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose, and copolymers thereof, and 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.
[0065]
As described above, by using the compound of the present invention in the light emitting layer of the organic EL element and further combining it with a specific hole injection layer or electron injection layer, the organic EL element characteristics such as luminous efficiency and maximum emission luminance are improved. We were able to. In addition, this device is extremely stable against heat and current, and furthermore, it can emit light that can be used practically at a low driving voltage, so that the deterioration, which has been a major problem until now, can be significantly reduced. Was completed.
[0066]
The organic EL device of the present invention can be applied to a flat panel display such as a wall-mounted television, a light source such as a copying machine or a printer, a light source such as a liquid crystal display or an instrument, a display board, or a sign lamp as a plane light emitter. , Its industrial value is very large.
[0067]
The material of the present invention can be used in the fields of organic EL devices, electrophotographic photoreceptors, photoelectric conversion devices, solar cells, image sensors and the like.
[0068]
【Example】
Hereinafter, the present invention will be described in more detail based on examples..
[0069]
Example 2
A compound (8) shown in Table 1 was vacuum-deposited on a washed glass plate with an ITO electrode to form a 100 nm-thick light-emitting layer, and a 10: 1 mixed alloy of magnesium and silver was formed thereon. An organic EL device was obtained by forming a 100 nm electrode. The light emitting layer is 10-6Vapor deposition was performed in a Torr vacuum at a substrate temperature of room temperature. This element is 110 (cd / m) at a DC voltage of 5 V.2), Maximum brightness 2200 (cd / m2), And luminescence with a luminous efficiency of 0.75 (lm / W) was obtained.
[0070]
Example 3
The compound (12) shown in Table 1 was dissolved in methylene chloride on a washed glass plate with an ITO electrode, and a 50 nm-thick light emitting layer was obtained by a spin coating method. Next, the compound (B-10) shown in Table 3 was vacuum-deposited to form an electron injection layer having a thickness of 30 nm, and an electrode having a thickness of 100 nm was formed on the electron injection layer by using a 10: 1 mixture of magnesium and silver. Thus, an organic EL device was obtained. The light emitting layer and the electron injection layer are 10-6Vapor deposition was performed in a Torr vacuum at a substrate temperature of room temperature. This element is 350 (cd / m) at a DC voltage of 5 V.2), Maximum brightness 5400 (cd / m2), And green light emission with a luminous efficiency of 1.3 (lm / W) was obtained.
[0071]
Example 4
The compound (16) shown in Table 1 was vacuum-deposited on the washed glass plate with an ITO electrode to form a light-emitting layer with a thickness of 50 nm. Next, the compound (B-3) shown in Table 3 was vacuum-deposited to form an electron injection layer having a thickness of 10 nm, and an electrode having a thickness of 100 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1. Thus, an organic EL device was obtained. The hole injection layer and the light emitting layer are 10-6Vapor deposition was performed in a Torr vacuum at a substrate temperature of room temperature. This element is approximately 410 (cd / m) at a DC voltage of 5 V.2), Maximum brightness 10,000 (cd / m2), Green light emission having a luminous efficiency of 1.6 (lm / W) was obtained.
[0072]
Examples 5 to 51
A hole injection material was vacuum-deposited on the washed glass plate with an ITO electrode under the conditions shown in Table 4 to obtain a hole injection layer having a thickness of 30 nm. Next, a luminescent material was vacuum-deposited to obtain a luminescent layer having a thickness of 30 nm. Further, an electron injecting material is vacuum-deposited to form an electron injecting layer having a thickness of 30 nm, and an electrode having a thickness of 150 nm is formed thereon by an alloy of magnesium and silver mixed at a ratio of 10: 1. An EL device was obtained. Each layer is 10-6Vapor deposition was performed in a Torr vacuum at a substrate temperature of room temperature. Table 4 shows the emission characteristics of this device. The emission luminance here is the luminance when a DC voltage of 5 V is applied, and all the organic EL elements of this embodiment have a maximum luminance of 10,000 (cd / m2).2) Had the above high luminance characteristics. Regarding the element configuration of the organic EL element, an element in which a hole-injecting material of the general formula [3] and an electron-injecting material of the general formula [4] were combined with the light emitting material of the general formula exhibited the best characteristics.
[0073]
[Table 4]
Example 52
The hole injecting material (A-13) was vacuum-deposited on the washed glass plate with ITO electrodes to obtain a hole injecting layer having a thickness of 40 nm. Next, the compound (8) was vacuum-deposited as a light emitting material to obtain a light emitting layer having a thickness of 40 nm. Further, (B-11) was vacuum-deposited as an electron injection material to obtain an electron injection layer having a thickness of 30 nm. An electrode having a thickness of 150 nm was formed thereon with an alloy of aluminum and lithium at a ratio of 50: 1 to obtain an organic EL device. This element has a DC voltage of 5 V and 8000 (cd / m2), Maximum brightness 131000 (cd / m2), And luminescence with a luminous efficiency of 13.8 (lm / W) was obtained.
[0075]
Example 53
An organic EL device was fabricated in the same manner as in Example 52, except that a hole injection layer having a thickness of 5 nm made of metal-free phthalocyanine was provided between the ITO electrode and the compound (A-13). This element has a DC voltage of 5 V and 10,000 (cd / m2), Maximum brightness 99000 (cd / m2), And luminescence with a luminous efficiency of 10.2 (lm / W) was obtained.
[0076]
Example 54
An organic EL device was produced in the same manner as in Example 48, except that a hole injection layer of a metal-free phthalocyanine having a thickness of 15 nm was provided instead of the compound (A-13). This element has a DC voltage of 5 V and 3500 (cd / m2), Maximum brightness 77000 (cd / m2), And luminescence with a luminous efficiency of 5.8 (lm / W) was obtained.
[0077]
Examples 55 to 64
An organic EL device was manufactured in the same manner as in Example 52, except that a 20 nm-thick light-emitting layer in which the compound (8) and the compound shown in Table 5 were deposited at a weight ratio of 100: 1 was used as the light-emitting layer. did. Table 6 shows the emission characteristics of this device. The emission luminance here is the luminance when a DC voltage of 5 V is applied, and all the organic EL elements of this embodiment have a maximum luminance of 10,000 (cd / m2).23.) High luminance characteristics as described above, and a desired emission color could be obtained.
[0078]
[Table 5]
[Table 6]
The organic EL element shown in this example has a light emission luminance of 10,000 (cd / m2), All of which were able to obtain high luminous efficiency. For the organic EL device shown in this example, 3 (mA / cm2), Stable light emission could be observed for 1000 hours or more, and almost no dark spots were observed. Since the organic EL device using the organic EL device material of the present invention has a very high fluorescence quantum efficiency of the light emitting material, in the device using this light emitting material, high luminance light emission in a low current application region becomes possible. Further, by using a doping material in addition to the compound of the general formula [1] in the light emitting layer, the maximum light emission luminance and the maximum light emission efficiency could be improved. Further, by adding a red-emitting or blue-emitting doping material to the compound of the general formula [1] emitting blue-green, green, and yellow light, a red-emitting or blue-emitting light-emitting element could be obtained. .
[0082]
The organic EL device of the present invention achieves improvement in luminous efficiency, luminous brightness and long life, and is used together with a luminescent material, a doping material, a hole injection material, an electron injection material, a sensitizer, and a resin. It does not limit the electrode material and the like, and the element manufacturing method.
[0083]
【The invention's effect】
An organic EL device using the organic EL device material of the present invention as a light emitting material showed high luminance light emission with higher luminous efficiency than the conventional one, and a long-life organic EL device was obtained. The compound shown in the present invention as described above is used in at least one layer of an organic EL device, and the organic EL device formed by the device configuration of the present invention has high luminance, high luminous efficiency, and long life. Can be easily manufactured.
Claims (7)
一般式［１］
一般式［２］
General formula [1]
General formula [2]
一般式［３］
General formula [3]
一般式［４］
General formula [4]
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| Application Number | Priority Date | Filing Date | Title |
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| JP07850196A JP3564859B2 (en) | 1996-04-01 | 1996-04-01 | Organic electroluminescent device material and organic electroluminescent device using the same |
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| JP07850196A JP3564859B2 (en) | 1996-04-01 | 1996-04-01 | Organic electroluminescent device material and organic electroluminescent device using the same |
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| Publication Number | Publication Date |
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| JPH09268284A JPH09268284A (en) | 1997-10-14 |
| JP3564859B2 true JP3564859B2 (en) | 2004-09-15 |
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Cited By (1)
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-
1996
- 1996-04-01 JP JP07850196A patent/JP3564859B2/en not_active Expired - Lifetime
Cited By (1)
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| WO2013185871A1 (en) | 2012-06-12 | 2013-12-19 | Merck Patent Gmbh | Compounds for electronic devices |
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