JP3666086B2 - Luminescent material for organic electroluminescence device and organic electroluminescence device using the same - Google Patents
Luminescent material for organic electroluminescence device and organic electroluminescence device using the same Download PDFInfo
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- JP3666086B2 JP3666086B2 JP32134895A JP32134895A JP3666086B2 JP 3666086 B2 JP3666086 B2 JP 3666086B2 JP 32134895 A JP32134895 A JP 32134895A JP 32134895 A JP32134895 A JP 32134895A JP 3666086 B2 JP3666086 B2 JP 3666086B2
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- light emitting
- organic
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- 239000000463 material Substances 0.000 title claims description 59
- 238000005401 electroluminescence Methods 0.000 title claims description 50
- -1 t-butoxy group Chemical group 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
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- 239000010409 thin film Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001725 pyrenyl group Chemical group 0.000 claims description 7
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
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- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
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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 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 67
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
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- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- VESMRDNBVZOIEN-UHFFFAOYSA-N 9h-carbazole-1,2-diamine Chemical compound C1=CC=C2C3=CC=C(N)C(N)=C3NC2=C1 VESMRDNBVZOIEN-UHFFFAOYSA-N 0.000 description 1
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- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
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- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
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- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 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
- 238000007740 vapor deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
Images
Description
【０００１】
【発明の属する技術分野】
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１００ｃｄ／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、大きな発光輝度を持ち、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素子用発光材料を発光層に使用した有機ＥＬ素子の発光輝度が高く、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発光材料に関する。
一般式［１］
【化２】
【０００７】
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層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、発光層が請求項１記載の有機エレクトロルミネッセンス素子用発光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。
【０００８】
さらに本発明は、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。
【０００９】
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。
【発明の実施の形態】
【００１０】
本発明における一般式［１］で示される置換基を有して良い芳香族環ＡもしくはＢとしては、ベンゼン環、ナフタレン環、アントラセン環、アズレニル環、ヘプタレニル環、アセナフチレニル環、ピレニル環等がある。
【００１１】
本発明における一般式［１］の芳香族環ＡもしくはＢに置換してもよい置換基の代表例としては、以下に示す置換基がある。水素原子、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アルコキシ基、置換もしくは未置換のアリール基、置換もしくは未置換のアミノ基を示し、隣接する置換基同士が互いに結合して芳香環を形成しても良い。
【００１２】
置換基の具体例としては、ハロゲン原子としては弗素、塩素、臭素、ヨウ素、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、ベンジル基、α，α−ジメチルベンジル基等がある。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、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、アントリル基、ピレニル基等がある。置換もしくは未置換のアミノ基としては、アミノ基、ジメチルアミノ基、ジエチルアミノ基、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、ジベンジルアミノ基等がある。また、隣接する置換基同士が互いに結合して、フェニル基、ナフチル基、アントリル基、ピレニル基等を形成しても良い。一般式［１］の中で、芳香族環を有している置換基を持つ、もしくは置換基同士で芳香族環を形成している化合物は、ガラス転移点や融点が高くなり、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ジュール熱による素子の劣化に対して有利である。本発明の化合物は、これらの置換基に限定されるものではない。
【００１３】
本発明の一般式［１］で示される化合物の合成方法の一例を以下に示す。
【００１４】
９−ハロゲノアントラセン、置換基を有しても良いジフェニルアミン誘導体、炭酸カリウムおよび触媒を溶媒中で反応させて、一般式［１］の化合物を合成する。また、アントラセン誘導体に代えてアントラキノン誘導体からも合成することができる。塩基としては、炭酸カリウムに代えて、炭酸ナトリウム、水酸化カリウム、水酸化ナトリウムまたはアンモニア水等を使用することができる。触媒としては、銅紛、塩化第一銅、スズ、塩化第一スズ、ピリジン、三塩化アルミニウムまたは四塩化チタンがある。溶媒は、ニトロベンゼン、１，３−ジメチル−２−イミダゾリジノン、ベンゼン、トルエンまたはキシレン等の高沸点溶媒であれはいずれでも良い。以上の合成法は、限定されるものではない。
【００１５】
以下に、本発明の化合物の代表例を、表１に具体的に示すが、本発明は、この代表例に限定されるものではない。
【００１６】
【表１】
本発明の一般式［１］で示される化合物は、固体状態で強い蛍光を持つため発光の濃度消光が少なく、電界印加時においても安定な化合物であるので、電界発光型素子の発光材料として優れている。また、正孔注入性や正孔輸送性も良好なので、正孔輸送型発光材料として有効に使用できる。また、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。
【００２１】
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。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、正孔輸送特性をもっているので、正孔注入型発光材料として発光層に使用できる。
【００２２】
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、および青色から赤色まで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。
【００２３】
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材料としては、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、マンガン等およびそれらの合金が用いられる。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、等があるがこれらに限定されるものではない。陽極および陰極は、必要があれば二層以上で形成されていても良い。
【００２４】
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、透明な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。
【００２５】
本発明に係わる有機ＥＬ素子の各層の形成は、真空蒸着、スパッタリング等の乾式成膜法やスピンコーティング、ディッピ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、各層は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。
【００２６】
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、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。
【００２７】
本有機ＥＬ素子は、発光層、正孔注入層、電子注入層において、必要があれば公知の発光材料、ドーピング材料、正孔注入材料、電子注入材料を使用することができる。
【００２８】
一般式［１］の化合物を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。
【００２９】
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。
【００３０】
本発明の有機ＥＬ素子において、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。具体的には、芳香族三級アミン誘導体としては、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’−（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。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。
【００３１】
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。
【００３２】
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。
【００３３】
本有機ＥＬ素子において、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、シリコンオイル等を封入して素子全体を保護することも可能である。
【００３４】
以上のように、本発明では有機ＥＬ素子に一般式［１］の化合物を用いたため、発光効率と発光輝度を高くできた。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。
【００３５】
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。
【００３６】
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。
【００３７】
【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。
化合物（８）の合成方法
ニトロベンゼン１０部、９−ブロモアントラセン１５部、４，４−ビス（α，α’−ジメチルベンジル）ジフェニルアミン２７部、および炭酸カリウム１２部、銅粉末０．８部を、２００℃にて３０時間加熱撹拌した。その後、５００部の水で希釈して、クロロホルムで抽出した。このクロロホルム層を濃縮し、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い、ｎ−ヘキサンで再沈澱をして黄色の蛍光を有する粉末１８部を得た。分子量分析の結果、化合物（８）であることを確認した。この化合物の赤外吸収スペクトル（ＫＢｒ錠剤法）を図１に示す。
【００３８】
実施例１
洗浄したＩＴＯ電極付きガラス板上に、化合物（４）、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２：３：５の比率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。この素子は、直流電圧５Ｖで１１０（ｃｄ／ｍ2 ）、発光効率１．０（ｌｍ／Ｗ）、発光色の色度は、ｘ＝０．３３０、ｙ＝０．５５０の発光が得られた。
【００３９】
実施例２
洗浄したＩＴＯ電極付きガラス板上に、化合物（５）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の正孔輸送型発光層を得た。次いで、ビス（２−メチル−８−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。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２２０（ｃｄ／ｍ2 ）、発光効率１．３（ｌｍ／Ｗ）、発光色の色度は、ｘ＝０．３３０、ｙ＝０．５４２の発光が得られた。
【００４０】
実施例３
洗浄したＩＴＯ電極付きガラス板上に、化合物（８）を真空蒸着して、膜厚５０ｎｍに正孔輸送型発光層を形成した。次いで、ビス（２−メチル−８−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。正孔注入層および発光層は１０- 6 Ｔｏｒｒ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３００ｃｄ／ｍ2 、発光効率１．５（ｌｍ／Ｗ）、発光色の色度は、ｘ＝０．３４０、ｙ＝０．５５８の発光が得られた。
【００４１】
実施例４〜１９
洗浄したＩＴＯ電極付きガラス板上に、下記化学構造で示される化合物（１７）を真空蒸着して、膜厚４０ｎｍの正孔注入層を得た。次いで、発光材料として表２の化合物を真空蒸着して膜厚３０ｎｍの発光層を得た。さらに、下記化学構造で示される化合物（１８）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印可時の輝度であり、本実施例の有機ＥＬ素子は、全て最高輝度１００００ｃｄ／ｍ2 以上であった。発光色の色度は、ｘ＝０．３３〜０．３４、ｙ＝０．５４〜０．５７の範囲の色度を持つ発光が得られた。また、一般式［１］の化合物としては、ＡもしくはＢの芳香族環基に芳香族環の置換基を持つ化合物（化合物８〜１０）、もしくは隣接した置換基で芳香族環を形成している化合物（化合物１１〜１６）が、ガラス転移点温度や融点温度が高く、発光駆動させた場合の劣化が少なく、寿命特性がさらに良好であった。
【化３】
【化４】
【００４２】
【表２】
実施例２０
洗浄したＩＴＯ電極付きガラス板上に、化合物（１７）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３０ｎｍの発光層を得た。さらに、２，５−ビス（１−ナフチル）−１，３，４−オキサジアゾールを真空蒸着して、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２０００ｃｄ／ｍ2 、発光効率３．３（ｌｍ／Ｗ）、発光色の色度は、ｘ＝０．３３０、ｙ＝０．５６０の発光が得られた。
【００４４】
実施例２１
ＩＴＯ電極と化合物（１７）との間に、無金属フタロシアニンの膜厚５ｎｍの正孔注入層を真空蒸着法により設ける以外は、実施例２０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２８００ｃｄ／ｍ2 、発光効率３．４（ｌｍ／Ｗ）、発光色の色度は、ｘ＝０．３３０、ｙ＝０．５５６の発光が得られた。実施例２０の有機ＥＬ素子に比べて、５Ｖ以下の低電圧発光時の輝度が高い利点がある。
【００４５】
本実施例で示された有機ＥＬ素子は、三層型以上の素子構成において、最大発光輝度１００００ｃｄ／ｍ2 以上の発光が得られ、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、３ｍＡ／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、正孔輸送材料、電子輸送材料、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。
【００４６】
【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。
【図面の簡単な説明】
【図１】化合物８の赤外吸収スペクトル[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a light-emitting material for organic electroluminescence (EL) elements and a high-luminance light-emitting element used for flat light sources and displays.
[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 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 a high luminance green light emission. The luminance is several hundred cd / m 2 at a direct current voltage of 6 to 7 V, maximum. The luminous efficiency is 1.5 lm / W, and the performance is close to the practical range.
[0004]
However, the organic EL elements 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 emission brightness and excellent stability in repeated use, it is desired to develop a light-emitting material having excellent luminous ability and durability. Yes.
[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] in the light emitting layer has high emission luminance and excellent stability during repeated use. As a result, the present invention has been accomplished.
[0006]
[Means for Solving the Problems]
The present invention relates to a light emitting material for an organic electroluminescence device represented by the following general formula [1].
General formula [1]
[Chemical formula 2]
[0007]
Furthermore, the present invention provides an organic electroluminescence device comprising a light emitting layer or a plurality of organic compound thin film layers including a light emitting layer between a pair of electrodes, wherein the light emitting layer is the light emitting material for an organic electroluminescent device according to
[0008]
Furthermore, the present invention is the above organic electroluminescence device, wherein a layer containing an aromatic tertiary amine derivative or a phthalocyanine derivative is formed between a light emitting layer and an anode.
[0009]
Furthermore, the present invention is the above-mentioned organic electroluminescence device, wherein a layer containing a metal complex compound or a nitrogen-containing five-membered ring derivative is formed between a light emitting layer and a cathode.
DETAILED DESCRIPTION OF THE INVENTION
[0010]
Examples of the aromatic ring A or B that may have a substituent represented by the general formula [1] in the present invention include a benzene ring, a naphthalene ring, an anthracene ring, an azulenyl ring, a heptaenyl ring, an acenaphthylenyl ring, and a pyrenyl ring. .
[0011]
Typical examples of the substituent that may be substituted on the aromatic ring A or B of the general formula [1] in the present invention include the following substituents. A hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, and adjacent substituents are bonded to each other. An aromatic ring may be formed.
[0012]
Specific examples of substituents include fluorine, chlorine, bromine, iodine as halogen atoms, and methyl, ethyl, propyl, butyl, sec-butyl, tert-butyl as substituted or unsubstituted alkyl groups. Group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, 2-phenylisopropyl group, trichloromethyl group, benzyl group, α, α-dimethylbenzyl group and the like. 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, phenoxy group and the like. Examples of the substituted or unsubstituted aryl group include a phenyl group, a biphenyl group, a terphenyl group, a 3,5-dichlorophenyl group, a naphthyl group, an anthryl group, and a pyrenyl group. Examples of the substituted or unsubstituted amino group include an amino group, a dimethylamino group, a diethylamino group, a phenylmethylamino group, a diphenylamino group, a ditolylamino group, and a dibenzylamino group. Further, adjacent substituents may be bonded to each other to form a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, or the like. In the general formula [1], a compound having a substituent having an aromatic ring or forming an aromatic ring with substituents has a high glass transition point and melting point, and an organic EL device When used as a light emitting material, it exhibits high light emission luminance and is advantageous for deterioration of the device due to Joule heat even when light is emitted for a long time. The compounds of the present invention are not limited to these substituents.
[0013]
An example of a method for synthesizing the compound represented by the general formula [1] of the present invention is shown below.
[0014]
A compound of the general formula [1] is synthesized by reacting 9-halogenoanthracene, an optionally substituted diphenylamine derivative, potassium carbonate and a catalyst in a solvent. Moreover, it can synthesize | combine from an anthraquinone derivative instead of the anthracene derivative. As the base, sodium carbonate, potassium hydroxide, sodium hydroxide, aqueous ammonia or the like can be used instead of potassium carbonate. Catalysts include copper powder, cuprous chloride, tin, stannous chloride, pyridine, aluminum trichloride or titanium tetrachloride. The solvent may be any high boiling point solvent such as nitrobenzene, 1,3-dimethyl-2-imidazolidinone, benzene, toluene or xylene. The above synthesis method is not limited.
[0015]
Specific examples of the compound of the present invention are specifically shown in Table 1 below, but the present invention is not limited to these representative examples.
[0016]
[Table 1]
Since the compound represented by the general formula [1] of the present invention has strong fluorescence in the solid state and has a low concentration quenching of light emission and is a stable compound even when an electric field is applied, it is excellent as a light emitting material for an electroluminescent element. ing. In addition, since the hole injecting property and hole transporting property are good, it can be used effectively as a hole transporting light emitting material. In addition, other hole transport materials, electron transport materials or doping materials may be used.
[0021]
An organic EL element is an element in which a single-layer or multilayer organic 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. The multilayer type is a multilayer of (anode / hole injection layer / light emitting layer / cathode), (anode / light emitting layer / electron injection layer / cathode), and (anode / hole injection layer / light emitting layer / electron injection layer / cathode). There are organic EL elements stacked in a configuration. The compound of the general formula [1] has high light emission characteristics, and has hole injection properties and hole transport properties, so that it can be used for a light emitting layer as a hole injection type light emitting material.
[0022]
If necessary, in addition to the compound of the general formula [1] of the present invention, a further light emitting material, doping material, hole injecting material and electron injecting material can be used for the light emitting layer. 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. In addition, the luminance and luminous efficiency can be improved by the doping material, and light emission from blue to red can be obtained. Further, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed with a layer configuration of two or more layers.
[0023]
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.
As the conductive material used for the cathode, a material having a work function smaller than 4 eV is suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, and alloys thereof are used. Examples of alloys include, but are not limited to, magnesium-silver, magnesium-indium, and lithium-aluminum. The anode and the cathode may be formed of two or more layers if necessary.
[0024]
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 is transparent, but examples include transparent resins such as glass substrates, polyethylene plates, polyethersulfone plates, and polypropylene plates. It is done.
[0025]
Formation of each layer of the organic EL device according to the present invention can be performed by any of dry film forming methods such as vacuum deposition and sputtering and wet film forming methods such as spin coating and dipping. The film thickness is not particularly limited, but each layer needs to 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.
[0026]
In the case of the wet film forming method, the 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 organic thin film layer, an appropriate resin or additive may be used for improving 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 light such as poly-N-vinylcarbazole and polysilane. Examples thereof include conductive resins such as conductive resins, polythiophene, and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.
[0027]
In the organic EL device, a known light emitting material, doping material, hole injecting material, and electron injecting material can be used in the light emitting layer, hole injecting layer, and electron injecting layer, if necessary.
[0028]
As a light emitting material or a doping material that can use the compound of the general formula [1] for the light emitting layer, 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 chelating oxinoid compounds, quinacridone, rubrene There are fine fluorescent dye or the like, but is not limited thereto.
[0029]
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 the electron injection layer or the electron injection material and have excellent thin film forming ability. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acyl hydrazone, polyaryl Alkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, etc., and their derivatives, and polymer materials such as polyvinyl carbazole, polysilane, conductive polymer, etc. However, it is not limited to these.
[0030]
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. Specifically, the aromatic tertiary amine derivatives include triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl- 4,4′-diamine, N, N, N′N ′-(4-methylphenyl) -1,1′-phenyl-4,4′-diamine, N, N, N′N ′-(4-methyl Phenyl) -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, etc. Or, these aromatic tertiary amine skeletons It is mer or polymers, etc., but is not limited thereto. Examples of phthalocyanine (Pc) derivatives include H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO) GaPc, VOPc, Examples include, but are not limited to, phthalocyanine derivatives such as TiOPc, MoOPc, GaPc-O-GaPc, and naphthalocyanine derivatives.
[0031]
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 layer 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.
[0032]
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-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolate) gallium, bis (2-methyl- 8-quinolinato) (1-naphtholate) aluminum, bis (2-mes There is Le-8-quinolinate) (2-naphtholato) gallium and the like, but is not limited thereto. 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, 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- ( -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.
[0033]
In this organic EL device, in addition to the compound of the general formula [1], 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, 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 silicon oil or the like is sealed to protect the entire device. It is also possible.
[0034]
As described above, in the present invention, since the compound of the general formula [1] is used for the organic EL element, the light emission efficiency and the light emission luminance can be increased. 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.
[0035]
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.
[0036]
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.
[0037]
【Example】
Hereinafter, the present invention will be described in more detail based on examples.
Synthesis method of compound (8) 10 parts of nitrobenzene, 15 parts of 9-bromoanthracene, 27 parts of 4,4-bis (α, α'-dimethylbenzyl) diphenylamine, 12 parts of potassium carbonate, 0.8 parts of copper powder, The mixture was heated and stirred at 200 ° C. for 30 hours. Thereafter, it was diluted with 500 parts of water and extracted with chloroform. The chloroform layer was concentrated, purified by column chromatography using silica gel, and reprecipitated with n-hexane to obtain 18 parts of powder having yellow fluorescence. As a result of molecular weight analysis, it was confirmed to be compound (8). The infrared absorption spectrum (KBr tablet method) of this compound is shown in FIG.
[0038]
Example 1
2 (2) compound (4), 2,5-bis (1-naphthyl) -1,3,4-oxadiazole, polycarbonate resin (Teijin Chemicals: Panlite K-1300) on the cleaned glass plate with ITO electrode Was dissolved in tetrahydrofuran at a ratio of 3: 5, 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. This device can emit light of 110 (cd / m 2 ) at a DC voltage of 5 V, luminous efficiency of 1.0 (lm / W), and chromaticity of emitted color of x = 0.330 and y = 0.550. It was.
[0039]
Example 2
On the washed glass plate with an ITO electrode, the compound (5) was dissolved in methylene chloride, and a hole transporting light emitting layer having a film thickness of 50 nm was obtained by a spin coating method. Next, a bis (2-methyl-8-quinolinato) (1-naphtholate) gallium complex is vacuum-deposited to form a 10 nm thick light-emitting layer, on which magnesium and silver are mixed at a ratio of 10: 1. An electrode having a thickness of 100 nm was formed to obtain an organic EL element. The hole injection layer and the light emitting layer were deposited in a vacuum of 10 −6 Torr at a substrate temperature of room temperature. This device emits light of 220 (cd / m 2 ) at a DC voltage of 5 V, luminous efficiency of 1.3 (lm / W), and chromaticity of emitted color of x = 0.330 and y = 0.542. It was.
[0040]
Example 3
On the washed glass plate with an ITO electrode, the compound (8) was vacuum-deposited to form a hole transporting light emitting layer with a film thickness of 50 nm. Next, a bis (2-methyl-8-quinolinato) (1-naphtholate) gallium complex is vacuum-deposited to form a 10 nm thick light-emitting layer, on which magnesium and silver are mixed at a ratio of 10: 1. An electrode having a thickness of 100 nm was formed to obtain an organic EL element. The hole injection layer and the luminescent layer 10 - in a 6 Torr vacuum, and deposited under a substrate temperature of room temperature. This device emitted light of about 300 cd / m 2 at a DC voltage of 5 V, a light emission efficiency of 1.5 (lm / W), and a chromaticity of emitted light of x = 0.340 and y = 0.558.
[0041]
Examples 4-19
On the washed glass plate with an ITO electrode, the compound (17) represented by the following chemical structure was vacuum-deposited to obtain a hole injection layer having a thickness of 40 nm. Subsequently, the compound of Table 2 was vacuum-deposited as a luminescent material, and the light emitting layer with a film thickness of 30 nm was obtained. Further, a compound (18) represented by the following chemical structure is vacuum-deposited to prepare an electron injection layer having a film thickness of 30 nm, and an alloy in which magnesium and silver are mixed at a ratio of 10: 1 is formed thereon with a film thickness of 150 nm. The electrode was formed to obtain an organic EL device. Each layer was deposited in a vacuum of 10 −6 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, and all the organic EL elements of this example had a maximum luminance of 10000 cd / m 2 or more. Light emission with chromaticity in the range of x = 0.33 to 0.34 and y = 0.54 to 0.57 was obtained. In addition, as the compound of the general formula [1], a compound having an aromatic ring substituent in the aromatic ring group of A or B (compounds 8 to 10), or an aromatic ring formed by an adjacent substituent. The compounds (compounds 11 to 16) had high glass transition temperature and melting point temperature, little deterioration when driven to emit light, and better life characteristics.
[Chemical 3]
[Formula 4]
[0042]
[Table 2]
Example 20
The compound (17) was vacuum-deposited on the washed glass plate with an ITO electrode to obtain a 40 nm-thick hole injection layer. Subsequently, the compound (8) was vacuum-deposited as a light emitting material to obtain a light emitting layer having a thickness of 30 nm. Further, 2,5-bis (1-naphthyl) -1,3,4-oxadiazole was vacuum deposited to obtain an electron injection layer having a thickness of 30 nm. 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. This device produced light emission of 2000 cd / m 2 at a DC voltage of 5 V, light emission efficiency of 3.3 (lm / W), and chromaticity of emission color of x = 0.330 and y = 0.560.
[0044]
Example 21
An organic EL device was produced in the same manner as in Example 20, except that a 5 nm thick hole injection layer of metal-free phthalocyanine was provided between the ITO electrode and the compound (17) by vacuum deposition. The device obtained light emission of 2800 cd / m 2 at a DC voltage of 5 V, light emission efficiency of 3.4 (lm / W), and chromaticity of emission color of x = 0.330 and y = 0.556. Compared to the organic EL element of Example 20, there is an advantage that the luminance at the time of low voltage light emission of 5 V or less is high.
[0045]
In the organic EL device shown in this example, light emission with a maximum light emission luminance of 10000 cd / m 2 or more was obtained in a three-layer or higher device structure, and all of the light emission efficiency could be obtained. When the organic EL device shown in this example was continuously emitted at 3 mA / cm 2 , stable emission could be observed for 1000 hours or more. The organic EL device of the present invention achieves improvement in luminous efficiency, luminous luminance and long life, and is used together with light emitting materials, doping materials, hole transport materials, electron transport materials, sensitizers, resins. The electrode material and the element manufacturing method are not limited.
[0046]
【The invention's effect】
The organic EL device using the organic EL device material of the present invention as a light emitting material showed high luminance and higher luminance than conventional ones, and a long-life organic EL device could be obtained.
[Brief description of the drawings]
FIG. 1 Infrared absorption spectrum of Compound 8
Claims (4)
一般式［１］
General formula [1]
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| Application Number | Priority Date | Filing Date | Title |
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| JP32134895A JP3666086B2 (en) | 1995-12-11 | 1995-12-11 | Luminescent material for organic electroluminescence device and organic electroluminescence device using the same |
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| JP32134895A JP3666086B2 (en) | 1995-12-11 | 1995-12-11 | Luminescent material for organic electroluminescence device and organic electroluminescence device using the same |
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| JP3666086B2 true JP3666086B2 (en) | 2005-06-29 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH1174079A (en) * | 1997-06-20 | 1999-03-16 | Nec Corp | Organic electroluminescent element |
| JP3503579B2 (en) | 1999-12-08 | 2004-03-08 | 日本電気株式会社 | Organic EL device and manufacturing method thereof |
| WO2002020693A1 (en) * | 2000-09-07 | 2002-03-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element |
| KR100817380B1 (en) * | 2000-10-05 | 2008-03-27 | 신닛테츠가가쿠 가부시키가이샤 | Organic electroluminescent devices |
| JP4139085B2 (en) | 2001-02-15 | 2008-08-27 | 三星エスディアイ株式会社 | Organic EL device and manufacturing method thereof |
| KR100667063B1 (en) | 2003-05-08 | 2007-01-10 | 삼성에스디아이 주식회사 | Method of manufacturing a substrate for organic electroluminescent display device |
| JP3848306B2 (en) | 2003-06-27 | 2006-11-22 | キヤノン株式会社 | Anthryl derivative-substituted compound and organic light emitting device using the same |
| JP4035482B2 (en) | 2003-06-27 | 2008-01-23 | キヤノン株式会社 | Substituted anthryl derivative and organic light emitting device using the same |
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| JP3840235B2 (en) | 2003-06-27 | 2006-11-01 | キヤノン株式会社 | Organic light emitting device |
| TW200535134A (en) | 2004-02-09 | 2005-11-01 | Nippon Steel Chemical Co | Aminodibenzodioxin derivative and organic electroluminescent device using same |
| JP4955971B2 (en) | 2004-11-26 | 2012-06-20 | キヤノン株式会社 | Aminoanthryl derivative-substituted pyrene compound and organic light-emitting device |
| JP4599142B2 (en) | 2004-11-26 | 2010-12-15 | キヤノン株式会社 | Organic light emitting device |
| CN101223138B (en) * | 2005-07-14 | 2011-03-09 | 株式会社半导体能源研究所 | Carbazole derivative, material for light emitting element, light emitting element and electronic device obtained by using the same |
| JP5041752B2 (en) * | 2005-07-27 | 2012-10-03 | 株式会社半導体エネルギー研究所 | Anthracene derivatives, materials for light emitting elements, light emitting elements, light emitting devices, and electronic devices |
| WO2007013537A1 (en) * | 2005-07-27 | 2007-02-01 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene derivative, material for light emitting element, light emitting element, light emitting device, and electronic appliance |
| JP2007230951A (en) | 2006-03-02 | 2007-09-13 | Canon Inc | Silyl compound, luminescent material and organic electroluminescent element using the same |
| TW200907021A (en) * | 2007-06-01 | 2009-02-16 | Du Pont | Blue luminescent materials |
| WO2008156088A1 (en) * | 2007-06-18 | 2008-12-24 | Idemitsu Kosan Co., Ltd. | Trinaphthyl monoamine or derivative thereof, organic electroluminescent device using the same, and organic electroluminescent material-containing solution |
| JP5606001B2 (en) * | 2009-03-19 | 2014-10-15 | 三井化学株式会社 | Aromatic amine derivatives and organic electroluminescent devices using them |
| JP6182884B2 (en) * | 2013-02-05 | 2017-08-23 | 日産化学工業株式会社 | Charge transport varnish |
| JP6547792B2 (en) * | 2017-06-12 | 2019-07-24 | 日産化学株式会社 | Charge transporting varnish |
| KR20200098753A (en) | 2019-02-11 | 2020-08-21 | 삼성디스플레이 주식회사 | Organic electroluminescence device and monoamine compound for organic electroluminescence device |
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