JP3575104B2 - Hole transport material and its use - Google Patents
Hole transport material and its use Download PDFInfo
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- JP3575104B2 JP3575104B2 JP6569795A JP6569795A JP3575104B2 JP 3575104 B2 JP3575104 B2 JP 3575104B2 JP 6569795 A JP6569795 A JP 6569795A JP 6569795 A JP6569795 A JP 6569795A JP 3575104 B2 JP3575104 B2 JP 3575104B2
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 238000012360 testing method Methods 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
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
Landscapes
- Photoreceptors In Electrophotography (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Led Devices (AREA)
- Electroluminescent Light Sources (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
- Luminescent Compositions (AREA)
Description
【０００１】
【産業上の利用分野】
本発明はトリフェニルアミン構造を有する正孔輸送材料に関し、該トリフェニルアミン化合物は、感光材料、有機光導電材料として使用でき、さらに具体的には、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）素子もしくは電子写真感光体等の正孔輸送材料として利用できる。
【０００２】
【従来の技術】
感光材料や正孔輸送材料として開発されている有機光導電材料は、低コスト、加工性が多様であり、無公害性などの多くの利点があり、多くの化合物が提案されている。例えば、オキサジアゾール誘導体（米国特許第３，１８９，４４７号）、オキサゾール誘導体（米国特許第３，２５７，２０３号）、ヒドラゾン誘導体（米国特許第３，７１７，４６２号、特開昭５４−５９，１４３号、米国特許第４，１５０，９７８号）、トリアリールピラゾリン誘導体（米国特許第３，８２０，９８９号、特開昭５１−９３，２２４号、特開昭５５−１０８，６６７号）、アリールアミン誘導体（米国特許第３，１８０，７３０号、米国特許第４，２３２，１０３号、特開昭５５−１４４，２５０号、特開昭５６−１１９，１３２号）、スチルベン誘導体（特開昭５８−１９０，９５３号、特開昭５９−１９５，６５８号）などの有機光導電性材料が開示されている。
【０００３】
正孔輸送材料を利用した技術の一つとしては、有機ＥＬ素子が挙げられる。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。
【０００４】
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蛍光体層、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。
【０００５】
しかしながら、現在までの有機ＥＬ素子は、発光輝度や繰り返し使用時の発光安定性は未だ充分ではない。従って、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、優れた正孔輸送能力を有し、耐久性のある正孔輸送材料の開発が望まれている。
【０００６】
さらに、正孔輸送材料を利用した技術としては、電子写真感光体が挙げられる。電子写真方式は、カールソンにより発明された画像形成法の一つである。この方式は、コロナ放電により感光体を帯電した後、光像露光して感光体に静電潜像を得、該静電潜像にトナーを付着させて現像し、得られたトナー像を紙へ転写することからなる。このような電子写真方式における感光体に要求される基本的な特性としては、暗所において適当な電位が保持されること、暗所における電荷の放電が少ないこと、光照射により速やかに電荷を放電することなどが挙げられる。従来までの電子写真感光体は、セレン、セレン合金、酸化亜鉛、硫化カドミウムおよびテルルなどの無機光導電体が使用されてきた。これらの無機光導電体は、耐久性が高く、耐刷枚数が多いなどの利点を有しているが、製造コストが高く、加工性が劣り、毒性を有するなどの問題点が指摘されている。これらの欠点を克服するために有機感光体の開発が行われているが、従来までの有機光導電材料を正孔輸送材料として用いた電子写真感光体は、帯電性、感度および残留電位などの電子写真特性が、必ずしも満足されているとは言えないのが現状であり、優れた電荷輸送能力を有し、耐久性のある正孔輸送材料の開発が望まれていた。
【０００７】
【発明が解決しようとする課題】
本発明の目的は、優れた正孔輸送能力を有し、耐久性のある正孔輸送材料を提供することにあり、さらにこの正孔輸送材料を繰り返して使用した際の安定性の優れた有機ＥＬ素子、電子写真感光体等を提供することを目的とする。
【０００８】
【課題を解決するための手段】
本発明者らは鋭意検討した結果、一般式［１］で示される少なくとも一種の正孔輸送材料は、正孔輸送能力が大きく、これを用いて作製した有機ＥＬ素子もしくは電子写真感光体等の素子の感度もしくは繰り返し使用時での安定性が優れていることを見いだし本発明に至った。
一般式［１］
【０００９】
【化２】
［式中、Ｒ1〜Ｒ8、Ｒ9〜Ｒ14は、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チオアルコキシ基、シアノ基、アミノ基、モノまたはジ置換アミノ基、水酸基、メルカプト基、置換もしくは未置換のアリールオキシ基、置換もしくは未置換のアリールチオ基、置換もしくは未置換の炭素環式芳香族環基、置換もしくは未置換の複素環式芳香族環基、置換もしくは未置換の複素環基を表す（隣接した置換基同士で置換もしくは未置換の脂肪族式環、置換もしくは未置換の炭素環式芳香族環、置換もしくは未置換の複素環式芳香族環基、置換もしくは未置換の複素環を形成しても良い。）。ｎは２〜７の整数を表す。
ただし、一般式［１］中の部分構造式
である骨格を含む場合を除く。］
【００１１】
更に本発明は、一対の電極間に、一層または複数層の有機化合物薄膜よりなる発光層を備えた有機エレクトロルミネッセンス素子において、少なくとも一層が一般式［１］で示される化合物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。
【００１２】
更に本発明は、導電性支持体上に、電荷発生材料および正孔輸送材料を使用してなる電子写真感光体において、正孔輸送材料が、一般式［１］で示される化合物であることを特徴とする電子写真感光体である。
【００１３】
本発明における一般式［１］で示される化合物の、Ｒ１〜Ｒ８およびＲ９〜Ｒ１４の具体例は、ハロゲン原子としては弗素、塩素、臭素、ヨウ素がある。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、トリクロロメチル基、トリフロロメチル基、シクロプロピル基、シクロヘキシル基、１，３−シクロヘキサジエニル基、２−シクロペンテン−１−イル基、２，４−シクロペンタジエン−１−イリデニル基等がある。置換もしくは未置換のアルコキシ基としては、メトキシ基、エトキシ基、プロポキシ基、ｎ−ブトキシ基、ｓｅｃ−ブトキシ基、ｔｅｒｔ−ブトキシ基、ペンチルオキシ基、ヘキシルオキシ基、ステアリルオキシ基、トリフロロメトキシ基等がある。置換もしくは未置換のチオアルコキシ基としては、メチルチオ基、エチルチオ基、プロピルチオ基、ブチルチオ基、ｓｅｃ−ブチルチオ基、ｔｅｒｔ−ブチルチオ基、ペンチルチオ基、ヘキシルチオ基、ヘプチルチオ基、オクチルチオ基等がある。
【００１４】
モノまたはジ置換アミノ基としては、メチルアミノ基、ジメチルアミノ基、エチルアミノ基、ジエチルアミノ基、ジプロピルアミノ基、ジブチルアミノ基等のアルキル基置換アミノ基、ジフェニルアミノ基、ジトリルアミノ基等の炭素環式芳香族アミノ基、ビス（アセトオキシメチル）アミノ基、ビス（アセトオキシエチル）アミノ基、ビス（アセトオキシプロピル）アミノ基、ビス（アセトオキシブチル）アミノ基、ジベンジルアミノ基等がある。置換もしくは未置換のアリールオキシ基としては、フェノキシ基、ｐ−ｔｅｒｔ−ブチルフェニキシ基、３−フルオロフェニキシ基等がある。置換もしくは未置換のアリールチオ基としては、フェニルチオ基、３−フルオロフェニルチオ基等がある。置換もしくは未置換の炭素環式芳香族環基としては、フェニル基、ビフェニレニル基、トリフェニレニル基、テトラフェニレニル基、３−ニトロフェニル基、４−メチルチオフェニル基、３，５−ジシアノフェニル基、ｏ−，ｍ−およびｐ−トリル基、キシリル基、ｏ−，ｍ−およびｐ−クメニル基、メシチル基、ペンタレニル基、インデニル基、ナフチル基、アズレニル基、ヘプタレニル基、アセナフチレニル基、フェナレニル基、フルオレニル基、アントリル基、アントラキノニル基、３−メチルアントリル基、フェナントリル基、トリフェニレニル基、ピレニル基、クリセニル基、２−エチル−１−クリセニル基、ピセニル基、ペリレニル基、６−クロロペリレニル基、ペンタフェニル基、ペンタセニル基、テトラフェニレニル基、ヘキサフェニル基、ヘキサセニル基、ルビセニル基、コロネニル基、トリナフチレニル基、ヘプタフェニル基、ヘプタセニル基、ピラントレニル基、オバレニル基等がある。
【００１５】
置換もしくは未置換の複素環式芳香族環基としては、チオニル基、フリル基、ピロリル基、イミダゾリル基、ピラゾリル基、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、インドリル基、キノリル基、イソキノリル基、フタラジニル基、キノキサリニル基、キナゾリニル基、カルバゾリル基、アクリジニル基、フェナジニル基、フルフリル基、イソチアゾリル基、イソキサゾリル基、フラザニル基、フェノキサジニル基、ベンゾチアゾリル基、ベンゾオキサゾリル基、ベンズイミダゾリル基、２−メチルピリジル基、３−シアノピリジル基等がある。
【００１６】
好ましいＲ９〜Ｒ１４としては、水素原子（この場合は無置換体となる。）炭素原子が１〜４の低級アルキル基もしくは低級アルコキシ基である。
また、隣接した置換基同士で５ないし７員環の酸素原子、窒素原子、硫黄原子等が含まれてもよい脂肪族、炭素環式芳香族、複素環式芳香族、複素環を形成してもよく、これらの環の任意の位置にさらに置換基を有していてもよい。
【００１７】
本発明における一般式［１］で示されるｎが２である化合物の具体例としては、１−インデンもしくは２−インデンがある。また、ｎが３である化合物の具体例としては、１−テトラリンもしくは、２−テトラリン等を挙げることができる
。
本発明の一般式［１］で示される化合物は、例えば以下の方法により製造することができる。
【００１８】
一般式［１］の化合物は、一般式［２］の基本骨格のアミノ基に、ハロゲン置換の相当するベンゼン誘導体を、窒素雰囲気下、有機溶媒中で、塩化銅を触媒として、所定の温度、所定の時間反応させて得ることが出来る。
【００１９】
さらに詳しくは、一般式［２］の化合物に、ヨードベンゼン誘導体もしくはブロモベンゼン誘導体を１，３−ジメチル−２−イミダゾリジノン等の高沸点有機溶媒中で、苛性ソーダ、炭酸カリウム等の塩基および塩化第１銅を触媒に用いて、脱ハロゲン反応させることにより、一般式［１］で示されるトリフェニルアミン誘導体を製造することができる。
一般式［２］
【００２０】
【化３】
以下に、本発明の化合物の代表例を表１に具体的に例示するが、本発明は以下の代表例に限定されるものではない。
【００２２】
【表１】
本発明の正孔輸送材料は、他の正孔もしくは電子輸送性化合物と混合して使用してもさしつかえない。本発明の化合物は正孔輸送性に優れているので、正孔輸送性材料として極めて有効に使用することができる。
【００２９】
まず、一般式［１］で示される化合物を有機ＥＬ素子の正孔輸送材料として用
いる場合について説明する。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輸送材料もしくは電子輸送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素子があり、一般式［１］の化合物は、どの素子構成においても好適に使用することが出来る。一般式［１］の化合物は、大きな正孔輸送能力をもっているので、正孔注入層もしくは発光層のいずれの層においても、正孔輸送材料として使用できる。有機ＥＬ素子では、必要があれば、発光物質、発光補助材料、キャリア注入もしくは輸送を行う正孔輸送材料や電子輸送材料を組み合わせて使用することもできる。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。
【００３０】
有機ＥＬ素子の陽極に使用される導電性物質としては、４ｅＶより大きな仕事関数を持つものが好適であり、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基板と称される酸化スズ、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好適であり、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の層構成により形成されていても良い。
【００３１】
有機ＥＬ素子では、効率良く発光させるために、陰極または陽極電極のうち、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、上記した導電性物質を使用して、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。発光面の電極の光透過率は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。
【００３２】
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の範囲が好適であるが、１０ｎｍから０．２μｍの範囲がさらに好ましい。
【００３３】
湿式成膜法の場合、各層を形成する材料を、クロロフォルム、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し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、いずれの薄膜においても、成膜性向上、膜のピンホール防止等のため適切な樹脂や添加剤を使用しても良い。
このような樹脂としては、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。
【００３４】
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、一般式［１］の化合物に加えて、公知の発光物質、発光補助材料、正孔輸送材料、電子輸送材料を使用することもできる。
【００３５】
公知の発光物質または発光物質の補助材料としては、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、オキシン、アミノキノリン、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、ルブレン等および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。
【００３６】
一般式［１］の正孔輸送材料と併せて使用できる正孔輸送材料としては、正孔を輸送する能力を持ち、発光層または発光物質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輸送材料への移動を防止し、かつ薄膜形成能の優れた化合物が挙げられる。具体的には、フタロシアニン系化合物、ナフタロシアニン系化合物、ポルフィリン系化合物、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。
【００３７】
電子輸送材料としては、電子を輸送する能力を持ち、発光層または発光物質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または正孔輸送材料への移動を防止し、かつ薄膜形成能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、オキサジアゾール、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、正孔輸送材料に電子受容物質を、電子輸送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。
【００３８】
本発明の一般式［１］の化合物は、有機ＥＬ素子のいずれの層にも使用することができ、一般式［１］の化合物の他に、発光物質、発光補助材料、正孔輸送材料および電子輸送材料の少なくとも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。
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。
【００３９】
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。
【００４０】
次に、本発明の一般式［１］で示される化合物を電子写真感光体として用いる場合について説明する。本発明の一般式［１］で示される化合物は、電子写真感光体の何れの層においても使用できるが、高い正孔輸送特性を有することから正孔輸送材料として使用することが望ましい。該化合物は正孔輸送材料として作用し、光を吸収することにより発生した電荷を極めて効率よく輸送でき、高速応答性の感光体を得ることができる。また、該化合物は、耐オゾン性、光安定性に優れているので、耐久性に優れた感光体を得ることができる。
【００４１】
電子写真感光体は、導電性基板上に電荷発生材料と、必要があれば電荷輸送材料を結着樹脂に分散させてなる感光層を設けた単層型感光体、導電性基板上に下引き層、電荷発生層、正孔輸送層の順に積層した、もしくは導電性基板または下引き層上に正孔輸送層、電荷発生層の順に積層した積層型感光体等がある。ここで、下引き層は必要がなければ使用しなくても良い。上記感光体は、必要があれば活性ガスからの表面保護およびトナーによるフィルミング防止等の意味でオーバーコート層を設けることも出来る。
【００４２】
電荷発生材料としては、ビスアゾ、キナクリドン、ジケトピロロピロール、インジゴ、ペリレン、ペリノン、多環キノン、スクアリリウム塩、アズレニウム塩、フタロシアニン、ナフタロシアニン等の有機化合物、もしくは、セレン、セレン−テルル合金、硫化カドミウム、酸化亜鉛、アモルファスシリコン等の無機物質が挙げられる。
【００４３】
感光体の各層は蒸着もしくは分散塗工方式により成膜することが出来る。分散塗工は、スピンコーター、アプリケーター、スプレーコーター、浸漬コーター、ローラーコーター、カーテンコーターおよびビードコーター等を用いて行い、乾燥は室温から２００℃、１０分から６時間の範囲で静止または送風条件下で行う。乾燥後の感光層の膜厚は単層型感光体の場合、５μｍから５０μｍ、積層型感光体の場合、電荷発生層は０．０１μｍから５μｍ、好ましくは０．１μｍから１μｍであり、正孔輸送層は５μｍから５０μｍ、好ましくは１０μｍから２０μｍが好適である。
【００４４】
単層型感光体の感光層、積層型感光体の電荷発生層もしくは正孔輸送層を形成する際に使用する樹脂は広範な絶縁性樹脂から選択出来る。また、ポリ−Ｎ−ビニルカルバゾール、ポリビニルアントラセンやポリシラン類などの有機光導電性ポリマーから選択出来る。好ましくは、ポリビニルブチラール、ポリアリレート、ポリカーボネート、ポリエステル、フェノキシ、アクリル、ポリアミド、ウレタン、エポキシ、シリコン、ポリスチレン、ポリ塩化ビニル、塩酢ビ共重合体、フェノールおよびメラミン樹脂等の絶縁性樹脂を挙げることが出来る。電荷発生層もしくは正孔輸送層を形成するために使用される樹脂は、電荷発生材料もしくは正孔輸送材料に対して、１００重量％以下が好ましいがこの限りではない。樹脂は２種類以上組み合わせて使用しても良い。また、必要があれば樹脂を使用しなくてもよい。また、電荷発生層を蒸着、スパッタリング等の物理的成膜法により形成させることも出来る。蒸着、スパッタリング法では、好ましくは１０−５Ｔｏｏｒ以下の真空雰囲気下で成膜することが望ましい。また、窒素、アルゴン、ヘリウム等の不活性ガス中で成膜することも可能である。
【００４５】
電子写真感光体の各層を形成する際に使用する溶剤は、下引き層や他の感光層に影響を与えないものから選択することが好ましい。具体的には、ベンゼン、キシレン等の芳香族炭化水素、アセトン、メチルエチルケトン、シクロヘキサノン等のケトン類、メタノール、エタノール等のアルコール類、酢酸エチル、メチルセロソルブ等のエステル類、四塩化炭素、クロロホルム、ジクロロメタン、ジクロロエタン、トリクロロエチレン等の脂肪族ハロゲン化炭化水素類、クロルベンゼン、ジクロルベンゼン等の芳香族ハロゲン化炭化水素類、テトラヒドロフラン、ジオキサン等のエーテル類等が用いられるがこれらに限られるものではない。
【００４６】
正孔輸送層は正孔輸送材料のみ、もしくは正孔輸送材料を樹脂に溶解させた塗液を塗布すること、もしくは蒸着等の乾式成膜法により形成される。本感光体に使用される正孔輸送材料は、一般式［１］の化合物に加えて他の正孔輸送材料を組み合わせて使用することもできる。一般式［１］の化合物は、樹脂との相溶性が良く、結晶として析出しにくいので、感度、耐久性の向上のために有利である。
【００４７】
電子写真特性、画像特性等の向上のために、必要があれば基板と有機層の間に下引き層を設けることができ、下引き層としてはポリアミド類、カゼイン、ポリビニルアルコール、ゼラチン、ポリビニルブチラール等の樹脂類、酸化アルミニウム等の金属酸化物などが用いられる。
【００４８】
本発明の材料は、有機ＥＬ素子もしくは電子写真感光体等の正孔輸送材料としのみでなく、光電変換素子、太陽電池、イメージセンサー、刷版等有機光導電材料のいずれの分野においても好適に使用できる。
【００４９】
【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（２）の合成方法
１，３−ジメチル−２−イミダゾリジノン８０部中に、１，１−ビス（４−アミノフェニル）−インドリン６．２５部、４−メチルヨードベンゼン７０部、および水酸化カリウム１８．９６部、塩化第１銅０．２部を入れ、２０５℃にて３０時間加熱撹拌した。冷却後、２００部の水で希釈し、この後、クロロホルムで抽出を行い、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して黄色の蛍光を有する粉末３部を得た。分子量分析、赤外線吸収スペクトルの結果、化合物（２）であることを確認した。
【００５０】
実施例１
洗浄したＩＴＯ電極付きガラス板上に、トリス（８−ヒドロキシキノリン）アルミニウム錯体、化合物（２）、ポリ−Ｎ−ビニルカルバゾールを３：２：５の比率でクロロホルムに溶解分散させ、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で混合して膜厚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で発光輝度８５ｃｄ／ｍ２、発光効率１．０ｌｍ／Ｗが得られた。
【００５１】
実施例２
洗浄したＩＴＯ電極付きガラス板上に、化合物（５）を真空蒸着して、膜厚３０ｎｍの正孔注入層を得た。次いで、トリス（８−ヒドロキシキノリン）アルミニウム錯体を真空蒸着して膜厚５０ｎｍの発光層を作成し、その上に、マグネシウムと銀を１０：１で混合して膜厚１５０ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入層および発光層は１０−６Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧５Ｖで発光輝度５２０ｃｄ／ｍ２、発光効率２．４ｌｍ／Ｗが得られた。
【００５２】
実施例３
洗浄したＩＴＯ電極付きガラス板上に、化合物（１０）を真空蒸着して、膜厚３０ｎｍの正孔注入層を得た。次いで、真空蒸着法によりトリス（８−ヒドロキシキノリン）アルミニウム錯体の膜厚２０ｎｍの発光層を作成し、さらに真空蒸着法により［２−（４−ｔｅｒｔ−ブチルフェニル）−５−（ビフェニル）−１，３，４−オキサジアゾール］の膜厚２０ｎｍの電子注入層を得た。その上に、マグネシウムと銀を１０：１で混合して膜厚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で発光輝度４５０ｃｄ／ｍ２、発光効率２．１ｌｍ／Ｗの発光が得られた。
【００５３】
本実施例で示された全ての有機ＥＬ素子について、２ｍＡ／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物質、発光補助材料、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。
【００５４】
実施例４
ε型銅フタロシアニン４ｇ、化合物（２）２ｇ、ポリエステル樹脂（東洋紡：バイロン２００）１４ｇをテトラヒドロフラン８０ｇと共にボールミルで５時間分散した。この分散液をアルミニウム基板上に塗工、乾燥して、膜厚２０μｍの単層型電子写真感光体を作製した。
【００５５】
実施例５
ジブロモアントアントロン６ｇ、化合物（１２）２ｇ、ポリエステル樹脂（東洋紡：バイロン２００）１２ｇをテトラヒドロフラン８０ｇと共にボールミルで５時間分散した。この分散液をアルミニウム基板上に塗工、乾燥して、膜厚２０μｍの単層型電子写真感光体を作製した。
【００５６】
実施例６
τ型無金属フタロシアニン２ｇ、ポリビニルブチラール樹脂（積水化学：ＢＨ−３）２ｇをテトラヒドロフラン９６ｇと共にボールミルで２時間分散した。この分散液をアルミニウム基板上に塗工、乾燥して、膜厚０．３μｍの電荷発生層を作製した。次に化合物（１３）１０ｇ、ポリカーボネート樹脂（帝人化成：Ｋ−１３００）１０ｇをジクロロメタン８０ｇに溶解した。この塗液を電荷発生層上に塗工、乾燥して、膜厚２０μｍの正孔輸送層を形成し、積層型電子写真感光体を作製した。
【００５７】
実施例７
Ｎ，Ｎ’−ビス（２，６−ジクロロフェニル）−３，４，９，１０−ペリレンジカルボキシイミド２ｇ、ポリビニルブチラール樹脂（積水化学：ＢＨ−３）２ｇをテトラヒドロフラン９６ｇと共にボールミルで２時間分散した。この分散液をアルミニウム基板上に塗工、乾燥して、膜厚０．３μｍの電荷発生層を作製した。次に化合物（１４）１０ｇ、ポリカーボネート樹脂（帝人化成：Ｋ−１３００）１０ｇをジクロロメタン８０ｇに溶解した。この塗液を電荷発生層上に塗工、乾燥して、膜厚２０ミクロンの正孔輸送層を形成し、積層型電子写真感光体を作製した。
【００５８】
電子写真感光体の電子写真特性は以下の方法で測定した。静電複写紙試験装置（川口電機製作所：ＥＰＡ−８１００）により、スタティックモード２、コロナ帯電は−５．２（ｋＶ）、５（ｌｕｘ）の白色光を照射して、初期表面電位（Ｖ０）、Ｖ０と２秒間暗所に放置した時の表面電位（Ｖ２）の比（暗減衰：ＤＤＲ２＝Ｖ２／Ｖ０）、光露光後に帯電量が初期の１／２まで減少する時間から半減露光量感度（Ｅ１／２）および光露光３秒後の表面電位（ＶＲ３）を調べた。実施例４〜７の電子写真感光体の電子写真特性を表２に示す。
【００５９】
【表２】
１万回以上繰り返して電子写真特性を測定したところ、本実施例で示された全ての電子写真感光体について、安定な表面電位、感度を得ることができた。
【００６１】
【発明の効果】
本発明により、優れた正孔輸送能力を有する化合物を得ることができた。本発明が提供した化合物は、従来に比べて高発光効率、高輝度であり、長寿命の有機ＥＬ素子および感度、正孔輸送特性、初期表面電位、暗減衰率等の初期電子写真特性に優れ、繰り返し使用に対する疲労も少ない電子写真感光体を得ることができた。[0001]
[Industrial applications]
The present invention relates to a hole transporting material having a triphenylamine structure, and the triphenylamine compound can be used as a photosensitive material or an organic photoconductive material, and more specifically, an organic electroluminescence used for a flat light source or display. It can be used as a hole transport material for (EL) devices or electrophotographic photoreceptors.
[0002]
[Prior art]
Organic photoconductive materials that have been developed as photosensitive materials and hole transport materials have many advantages such as low cost, various processability, and no pollution, and many compounds have been proposed. For example, oxadiazole derivatives (U.S. Pat. No. 3,189,447), oxazole derivatives (U.S. Pat. No. 3,257,203), hydrazone derivatives (U.S. Pat. 59,143, U.S. Pat. No. 4,150,978), triarylpyrazoline derivatives (U.S. Pat. No. 3,820,989, JP-A-51-93,224, JP-A-55-108,667). ), Arylamine derivatives (U.S. Pat. No. 3,180,730, U.S. Pat. No. 4,232,103, JP-A-55-144250, JP-A-56-119,132), stilbene derivatives (Japanese Patent Application Laid-Open Nos. 58-190,953 and 59-195,658) discloses organic photoconductive materials.
[0003]
One of the techniques using a hole transport material is an organic EL device. 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, 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. In addition, 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.
[0004]
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 phosphor layer and an amine compound for a hole injection layer to obtain high-luminance green light emission. The luminance is 100 cd / m 2 at a DC voltage of 6 to 7 V, and the maximum is 90 cd / m 2 . The luminous efficiency achieves 1.5 lm / W, which is a performance close to the practical range.
[0005]
However, the organic EL devices to date have not yet had sufficient light emission luminance and light emission stability upon repeated use. Therefore, in order to develop an organic EL device having higher emission luminance and excellent stability in repeated use, it is desired to develop a hole transporting material having excellent hole transporting ability and durability. It is rare.
[0006]
Further, as a technique using a hole transport material, an electrophotographic photoreceptor can be mentioned. The electrophotographic method is one of image forming methods invented by Carlson. In this method, after a photoconductor is charged by corona discharge, an optical image is exposed to obtain an electrostatic latent image on the photoconductor, toner is attached to the electrostatic latent image and developed, and the obtained toner image is printed on paper. Transfer to The basic characteristics required of the photoreceptor in such an electrophotographic method include that an appropriate potential is maintained in a dark place, that the electric charge is less discharged in the dark place, and that the electric charge is quickly discharged by light irradiation. And so on. Conventional electrophotographic photoreceptors have used inorganic photoconductors such as selenium, selenium alloys, zinc oxide, cadmium sulfide, and tellurium. These inorganic photoconductors have advantages such as high durability and a large number of printing presses, but problems such as high production cost, poor workability, and toxicity have been pointed out. . Organic photoreceptors have been developed to overcome these drawbacks.However, conventional electrophotographic photoreceptors using organic photoconductive materials as hole transporting materials have had problems in chargeability, sensitivity and residual potential. At present, it cannot be said that the electrophotographic characteristics are always satisfied, and it has been desired to develop a hole transporting material having excellent charge transporting ability and durability.
[0007]
[Problems to be solved by the invention]
An object of the present invention is to provide a hole transporting material having excellent hole transporting ability and durability, and an organic compound having excellent stability when this hole transporting material is repeatedly used. An object is to provide an EL element, an electrophotographic photosensitive member, and the like.
[0008]
[Means for Solving the Problems]
As a result of intensive studies, the present inventors have found that at least one kind of hole transporting material represented by the general formula [1] has a large hole transporting ability, and is used for an organic EL device or an electrophotographic photosensitive member manufactured using the same. The inventors have found that the sensitivity of the element or the stability during repeated use is excellent, and have reached the present invention.
General formula [1]
[0009]
Embedded image
[Wherein, R 1 to R 8 and R 9 to R 14 represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a cyano group , Amino group, mono- or di-substituted amino group, hydroxyl group, mercapto group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted carbocyclic aromatic ring group, substituted or unsubstituted Represents a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted carbocyclic aromatic ring, An unsubstituted heterocyclic aromatic ring group or a substituted or unsubstituted heterocyclic ring may be formed.) n represents an integer of 2 to 7.
However, the partial structural formula in the general formula [1]
Excluding the case where the skeleton is included. ]
[0011]
Further, the present invention provides an organic electroluminescence device having a light emitting layer composed of one or more organic compound thin films between a pair of electrodes, wherein at least one layer contains a compound represented by the general formula [1]. It is an organic electroluminescence element.
[0012]
Further, the present invention provides an electrophotographic photosensitive member using a charge generation material and a hole transport material on a conductive support, wherein the hole transport material is a compound represented by the general formula [1]. Characteristic electrophotographic photoreceptor.
[0013]
Specific examples of R 1 to R 8 and R 9 to R 14 of the compound represented by the general formula [1] in the present invention include fluorine, chlorine, bromine and iodine as halogen atoms. Examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group, and a trichloromethyl group. Trifluoromethyl group, cyclopropyl group, cyclohexyl group, 1,3-cyclohexadienyl group, 2-cyclopenten-1-yl group, 2,4-cyclopentadiene-1-yridenyl group and the like. Examples of the substituted or unsubstituted alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a stearyloxy group, and a trifluoromethoxy group. Etc. Examples of the substituted or unsubstituted thioalkoxy group include methylthio, ethylthio, propylthio, butylthio, sec-butylthio, tert-butylthio, pentylthio, hexylthio, heptylthio, octylthio, and the like.
[0014]
Examples of the mono- or di-substituted amino group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a dipropylamino group, and a carbon ring such as a diphenylamino group and a dibutylamino group. Formula aromatic amino group, bis (acetooxymethyl) amino group, bis (acetooxyethyl) amino group, bis (acetooxypropyl) amino group, bis (acetooxybutyl) amino group, dibenzylamino group and the like. Examples of the substituted or unsubstituted aryloxy group include a phenoxy group, a p-tert-butylphenoxy group, and a 3-fluorophenoxy group. Examples of the substituted or unsubstituted arylthio group include a phenylthio group and a 3-fluorophenylthio group. As a substituted or unsubstituted carbocyclic aromatic ring group, a phenyl group, a biphenylenyl group, a triphenylenyl group, a tetraphenylenyl group, a 3-nitrophenyl group, a 4-methylthiophenyl group, a 3,5-dicyanophenyl group, o-, m- and p-tolyl group, xylyl group, o-, m- and p-cumenyl group, mesityl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, acenaphthylenyl group, phenalenyl group, fluorenyl Group, anthryl group, anthraquinonyl group, 3-methylanthryl group, phenanthryl group, triphenylenyl group, pyrenyl group, chrysenyl group, 2-ethyl-1-chrysenyl group, picenyl group, perylenyl group, 6-chloroperylenyl group, pentaphenyl group , Pentacenyl group, tetraphenylenyl group, f Safeniru group, hexacenyl group, rubicenyl group, coronenyl groups, trinaphthylenyl groups, heptacenyl groups, pyranthrenyl groups, and the like ovalenyl group.
[0015]
Examples of the substituted or unsubstituted heterocyclic aromatic ring group include a thionyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, a quinolyl group, and an isoquinolyl group , Phthalazinyl, quinoxalinyl, quinazolinyl, carbazolyl, acridinyl, phenazinyl, furfuryl, isothiazolyl, isoxazolyl, furazanyl, phenoxazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, 2-methyl There are a pyridyl group and a 3-cyanopyridyl group.
[0016]
Preferred R 9 to R 14 are a hydrogen atom (in this case, an unsubstituted product), a lower alkyl group or a lower alkoxy group having 1 to 4 carbon atoms.
Adjacent substituents form an aliphatic, carbocyclic aromatic, heteroaromatic, or heterocyclic ring which may contain a 5- to 7-membered oxygen atom, nitrogen atom, sulfur atom, etc. And a substituent may be further provided at any position of these rings.
[0017]
Specific examples of the compound represented by the general formula [1] in which n is 2 include 1-indene or 2-indene. Further, specific examples of the compound in which n is 3 include 1-tetralin and 2-tetralin.
The compound represented by the general formula [1] of the present invention can be produced, for example, by the following method.
[0018]
The compound of the general formula [1] is obtained by adding a halogen-substituted benzene derivative to an amino group of the basic skeleton of the general formula [2] in an organic solvent under a nitrogen atmosphere at a predetermined temperature using copper chloride as a catalyst. It can be obtained by reacting for a predetermined time.
[0019]
More specifically, an iodobenzene derivative or a bromobenzene derivative is added to a compound of the general formula [2] in a high boiling organic solvent such as 1,3-dimethyl-2-imidazolidinone and a base such as caustic soda and potassium carbonate and chloride. By performing a dehalogenation reaction using copper (I) as a catalyst, a triphenylamine derivative represented by the general formula [1] can be produced.
General formula [2]
[0020]
Embedded image
Hereinafter, typical examples of the compound of the present invention are specifically shown in Table 1, but the present invention is not limited to the following typical examples.
[0022]
[Table 1]
The hole transport material of the present invention may be used in a mixture with another hole or electron transport compound. Since the compound of the present invention has excellent hole transporting properties, it can be used very effectively as a hole transporting material.
[0029]
First, a case where the compound represented by the general formula [1] is used as a hole transport material of an organic EL device will be described. 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 an anode and a cathode. The light emitting layer contains a light emitting material, and may further contain a hole transporting material or an electron transporting material for transporting holes injected from an anode or electrons injected from a cathode to the light emitting material. 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 device stacked in a configuration, and the compound of the general formula [1] can be suitably used in any device configuration. Since the compound of the general formula [1] has a large hole transporting ability, it can be used as a hole transporting material in any of the hole injection layer and the light emitting layer. In the organic EL element, if necessary, a luminescent substance, a luminescent auxiliary material, a hole transporting material for injecting or transporting carriers, or an electron transporting material can be used in combination. Further, each of the hole injection layer, the light emitting layer, and the electron injection layer may be formed with two or more layers.
[0030]
As the conductive substance used for the anode of the organic EL element, those having a work function larger than 4 eV are preferable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, etc. And alloys thereof, metal oxides such as tin oxide and indium oxide, which are called ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole. As the conductive material used for the cathode, those having a work function smaller than 4 eV are preferable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, and the like and alloys thereof are used. However, the present invention is not limited to these. The anode and the cathode may be formed of two or more layers if necessary.
[0031]
In an organic EL device, it is desirable that at least one of a cathode and an anode be sufficiently transparent in an emission wavelength region of the device in order to efficiently emit light. Further, it is desirable that the substrate is also transparent. The transparent electrode is set so as to secure a predetermined light transmittance by a method such as vapor deposition or sputtering using the above-described conductive substance. The light transmittance of the electrode on the light emitting surface is desirably 10% or more.
The substrate is not limited as long as it has mechanical and thermal strength and is transparent, but examples thereof include a transparent resin such as a glass substrate, a polyethylene plate, a polyether sulfone plate, and a polypropylene plate. Can be
[0032]
Each layer of the organic EL device according to the present invention can be formed by any of dry film forming methods such as vacuum evaporation and sputtering and wet film forming methods such as spin coating and dipping. The thickness is not particularly limited, but each layer needs to be set to an appropriate 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 thickness is preferably in the range of 5 nm to 10 μm, but more preferably in the range of 10 nm to 0.2 μm.
[0033]
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 chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used. In any of the thin films, a suitable resin or additive may be used to improve film forming properties, prevent pinholes in the film, and the like.
Examples of such a resin include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose; and photoconductive materials such as poly-N-vinyl carbazole and polysilane. And conductive resins such as polythiophene and polypyrrole.
[0034]
The present organic EL device may include, if necessary, a known light-emitting substance, a light-emitting auxiliary material, a hole-transporting material, an electron-emitting layer, a hole-injecting layer, and an electron-injecting layer in addition to the compound of the general formula [1]. Transport materials can also be used.
[0035]
Known light-emitting substances or auxiliary materials for light-emitting substances include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthalopylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin, Oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, oxine, aminoquinoline, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, imidazole chelated oxinoid compound, quinacridone, Examples include, but are not limited to, rubrene and the like and derivatives thereof.
[0036]
The hole transporting material that can be used in combination with the hole transporting material of the general formula [1] has the ability to transport holes, has an excellent hole injecting effect on a light emitting layer or a light emitting substance, and emits light. Compounds that prevent excitons generated in the layer from migrating to the electron injection layer or the electron transporting material and have excellent thin film forming ability are exemplified. Specifically, phthalocyanine compounds, naphthalocyanine compounds, porphyrin compounds, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, poly There are arylalkanes, stilbenes, butadienes, benzidine-type triphenylamines, styrylamine-type triphenylamines, diamine-type triphenylamines, and derivatives thereof, and polymer materials such as polyvinylcarbazole, polysilane, and conductive polymers. However, the present invention is not limited to these.
[0037]
As an electron transport material, it has the ability to transport electrons, has an excellent electron injection effect on a light emitting layer or a light emitting substance, and transfers excitons generated in the light emitting layer to a hole injection layer or a hole transport material. Compounds that prevent migration and have excellent thin film forming ability can be used. Examples include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxadiazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, anthrone, and derivatives thereof. Not something.
In addition, sensitization can be performed by adding an electron accepting substance to the hole transporting material and adding an electron donating substance to the electron transporting material.
[0038]
The compound of the general formula [1] of the present invention can be used in any layer of an organic EL device. In addition to the compound of the general formula [1], a light emitting substance, a light emission auxiliary material, a hole transport material and At least one of the electron transporting materials may be contained in the same layer.
In order to improve the stability of the organic EL device obtained according to 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.
As described above, in the present invention, since the compound of the general formula [1] was used for the organic EL device, the luminous efficiency and the luminous brightness could be increased. 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.
[0039]
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.
[0040]
Next, the case where the compound represented by the general formula [1] of the present invention is used as an electrophotographic photosensitive member will be described. The compound represented by the general formula [1] of the present invention can be used in any layer of an electrophotographic photoreceptor, but is preferably used as a hole transporting material because of having high hole transporting properties. The compound acts as a hole transporting material, can transport charges generated by absorbing light extremely efficiently, and can provide a photoreceptor having a high-speed response. Further, since the compound is excellent in ozone resistance and light stability, a photosensitive member having excellent durability can be obtained.
[0041]
An electrophotographic photoreceptor is a single-layer type photoreceptor having a photosensitive layer formed by dispersing a charge generating material on a conductive substrate and, if necessary, a charge transporting material in a binder resin, and subbing on a conductive substrate. There is a laminated photoreceptor in which a layer, a charge generation layer, and a hole transport layer are laminated in this order, or a hole transport layer and a charge generation layer are laminated in this order on a conductive substrate or an undercoat layer. Here, the undercoat layer may not be used if unnecessary. If necessary, the photoreceptor may be provided with an overcoat layer for the purpose of protecting the surface from active gas and preventing filming with toner.
[0042]
As the charge generating material, organic compounds such as bisazo, quinacridone, diketopyrrolopyrrole, indigo, perylene, perinone, polycyclic quinone, squarylium salt, azurenium salt, phthalocyanine, and naphthalocyanine, or selenium, selenium-tellurium alloy, sulfide Examples include inorganic substances such as cadmium, zinc oxide, and amorphous silicon.
[0043]
Each layer of the photoreceptor can be formed by vapor deposition or dispersion coating. The dispersion coating is performed using a spin coater, an applicator, a spray coater, a dipping coater, a roller coater, a curtain coater, a bead coater, etc., and drying is performed at room temperature to 200 ° C. for 10 minutes to 6 hours under static or blowing conditions. Do. The thickness of the photosensitive layer after drying is 5 μm to 50 μm in the case of a single layer type photoreceptor, and 0.01 μm to 5 μm, preferably 0.1 μm to 1 μm in the case of a multilayer type photoreceptor. The transport layer has a thickness of 5 μm to 50 μm, preferably 10 μm to 20 μm.
[0044]
The resin used for forming the photosensitive layer of the single-layer type photoreceptor or the charge generation layer or the hole transport layer of the laminated type photoreceptor can be selected from a wide range of insulating resins. Further, it can be selected from organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene and polysilanes. Preferably, insulating resins such as polyvinyl butyral, polyarylate, polycarbonate, polyester, phenoxy, acrylic, polyamide, urethane, epoxy, silicone, polystyrene, polyvinyl chloride, polyvinyl chloride copolymer, phenol and melamine resin are mentioned. Can be done. The resin used for forming the charge generation layer or the hole transport layer is preferably 100% by weight or less based on the charge generation material or the hole transport material, but is not limited thereto. Two or more resins may be used in combination. Further, if necessary, the resin may not be used. Further, the charge generation layer can be formed by a physical film forming method such as vapor deposition and sputtering. In the evaporation and sputtering methods, it is preferable to form a film in a vacuum atmosphere of preferably 10 −5 Toor or less. It is also possible to form a film in an inert gas such as nitrogen, argon, and helium.
[0045]
The solvent used when forming each layer of the electrophotographic photoreceptor is preferably selected from those which do not affect the undercoat layer or other photosensitive layers. Specifically, aromatic hydrocarbons such as benzene and xylene, ketones such as acetone, methyl ethyl ketone and cyclohexanone, alcohols such as methanol and ethanol, esters such as ethyl acetate and methyl cellosolve, carbon tetrachloride, chloroform and dichloromethane But aliphatic halogenated hydrocarbons such as dichloroethane and trichloroethylene, aromatic halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, and ethers such as tetrahydrofuran and dioxane are used, but are not limited thereto.
[0046]
The hole transport layer is formed by applying only a hole transport material, a coating solution in which the hole transport material is dissolved in a resin, or a dry film forming method such as vapor deposition. The hole transport material used in the present photoreceptor can be used in combination with another hole transport material in addition to the compound represented by the general formula [1]. The compound represented by the general formula [1] has good compatibility with the resin and is not easily precipitated as a crystal, which is advantageous for improving sensitivity and durability.
[0047]
If necessary, an undercoat layer can be provided between the substrate and the organic layer to improve electrophotographic properties, image properties, and the like. Examples of the undercoat layer include polyamides, casein, polyvinyl alcohol, gelatin, and polyvinyl butyral. And the like, and metal oxides such as aluminum oxide.
[0048]
The material of the present invention is suitably used not only as a hole transport material such as an organic EL device or an electrophotographic photoreceptor, but also in any field of an organic photoconductive material such as a photoelectric conversion device, a solar cell, an image sensor, and a printing plate. Can be used.
[0049]
【Example】
Hereinafter, the present invention will be described in more detail with reference to Examples.
Synthesis method of compound (2) In 80 parts of 1,3-dimethyl-2-imidazolidinone, 6.25 parts of 1,1-bis (4-aminophenyl) -indoline, 70 parts of 4-methyliodobenzene, and 18.96 parts of potassium hydroxide and 0.2 parts of cuprous chloride were added, and the mixture was heated and stirred at 205 ° C. for 30 hours. After cooling, the mixture was diluted with 200 parts of water, extracted with chloroform, concentrated, and purified by column chromatography using silica gel to obtain 3 parts of a powder having yellow fluorescence. As a result of a molecular weight analysis and an infrared absorption spectrum, it was confirmed to be Compound (2).
[0050]
Example 1
Tris (8-hydroxyquinoline) aluminum complex, compound (2), and poly-N-vinylcarbazole were dissolved and dispersed in chloroform at a ratio of 3: 2: 5 on a washed glass plate with an ITO electrode, and spin-coated by spin coating. A light emitting layer having a thickness of 100 nm was obtained. On top of that, magnesium and silver were mixed at a ratio of 10: 1 to form an electrode having a thickness of 150 nm to obtain an organic EL device. This device had a luminance of 85 cd / m 2 and a luminous efficiency of 1.0 lm / W at a DC voltage of 5 V.
[0051]
Example 2
Compound (5) was vacuum-deposited on the washed glass plate with ITO electrodes to obtain a hole-injecting layer having a thickness of 30 nm. Then, a tris (8-hydroxyquinoline) aluminum complex was vacuum-deposited to form a 50-nm-thick light-emitting layer, and magnesium and silver were mixed at a ratio of 10: 1 to form a 150-nm-thick electrode. An organic EL device was obtained. 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 had a light emission luminance of 520 cd / m 2 and a light emission efficiency of 2.4 lm / W at a DC voltage of 5 V.
[0052]
Example 3
Compound (10) was vacuum-deposited on the washed glass plate with ITO electrodes to obtain a hole injection layer having a thickness of 30 nm. Next, a 20 nm-thick light-emitting layer of a tris (8-hydroxyquinoline) aluminum complex was formed by vacuum evaporation, and [2- (4-tert-butylphenyl) -5- (biphenyl) -1 was further formed by vacuum evaporation. , 3,4-oxadiazole] with a thickness of 20 nm. On top of that, magnesium and silver were mixed at a ratio of 10: 1 to form an electrode having a thickness of 150 nm to obtain an organic EL device. This device emitted light with a luminance of 450 cd / m 2 and a luminous efficiency of 2.1 lm / W at a DC voltage of 5 V.
[0053]
When continuous light emission was performed at 2 mA / cm 2 for all the organic EL elements shown in this example, stable light 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 a luminescent substance, a luminescent auxiliary material, a hole transport material, an electron transport material, a sensitizer, It does not limit the resin, the electrode material and the like, and the element manufacturing method.
[0054]
Example 4
4 g of ε-type copper phthalocyanine, 2 g of the compound (2), and 14 g of a polyester resin (Toyobo: Byron 200) were dispersed together with 80 g of tetrahydrofuran in a ball mill for 5 hours. This dispersion was applied on an aluminum substrate and dried to produce a 20 μm-thick single-layer electrophotographic photosensitive member.
[0055]
Example 5
6 g of dibromoanthanthrone, 2 g of the compound (12) and 12 g of a polyester resin (Toyobo: Byron 200) were dispersed together with 80 g of tetrahydrofuran in a ball mill for 5 hours. This dispersion was applied on an aluminum substrate and dried to produce a 20 μm-thick single-layer electrophotographic photosensitive member.
[0056]
Example 6
2 g of τ-type metal-free phthalocyanine and 2 g of polyvinyl butyral resin (Sekisui Chemical: BH-3) were dispersed together with 96 g of tetrahydrofuran in a ball mill for 2 hours. This dispersion was coated on an aluminum substrate and dried to form a charge generation layer having a thickness of 0.3 μm. Next, 10 g of the compound (13) and 10 g of a polycarbonate resin (T-1) were dissolved in 80 g of dichloromethane. This coating solution was applied on the charge generation layer and dried to form a hole transport layer having a thickness of 20 μm, thereby producing a laminated electrophotographic photosensitive member.
[0057]
Example 7
2 g of N, N'-bis (2,6-dichlorophenyl) -3,4,9,10-perylenedicarboximide and 2 g of polyvinyl butyral resin (Sekisui Chemical: BH-3) were dispersed in a ball mill for 2 hours together with 96 g of tetrahydrofuran. . This dispersion was coated on an aluminum substrate and dried to form a charge generation layer having a thickness of 0.3 μm. Next, 10 g of the compound (14) and 10 g of a polycarbonate resin (T-1) were dissolved in 80 g of dichloromethane. This coating solution was applied on the charge generation layer and dried to form a hole transport layer having a thickness of 20 μm, thereby producing a laminated electrophotographic photoreceptor.
[0058]
The electrophotographic characteristics of the electrophotographic photosensitive member were measured by the following method. Static mode 2, corona charging -5.2 (kV), 5 (lux) white light is irradiated by an electrostatic copying paper test apparatus (Kawaguchi Electric Works: EPA-8100), and the initial surface potential (V 0) ), The ratio of V 0 to the surface potential (V 2 ) when left in a dark place for 2 seconds (dark decay: DDR 2 = V 2 / V 0 ), and the amount of charge decreases to １ ／ of the initial value after light exposure From the time, the half-life exposure amount sensitivity (E 1/2 ) and the surface potential (VR 3 ) after 3 seconds of light exposure were examined. Table 2 shows the electrophotographic characteristics of the electrophotographic photosensitive members of Examples 4 to 7.
[0059]
[Table 2]
When the electrophotographic characteristics were measured repeatedly 10,000 times or more, stable surface potential and sensitivity could be obtained for all the electrophotographic photosensitive members shown in this example.
[0061]
【The invention's effect】
According to the present invention, a compound having excellent hole transporting ability can be obtained. The compound provided by the present invention has higher luminous efficiency and higher brightness than conventional ones, and has excellent long-lifetime organic EL devices and excellent initial electrophotographic properties such as sensitivity, hole transport properties, initial surface potential, and dark decay rate. Thus, an electrophotographic photoreceptor having less fatigue due to repeated use could be obtained.
Claims (3)
一般式［１］
ただし、一般式［１］中の部分構造式
である骨格を含む場合を除く。］A hole transport material represented by the following general formula [1].
General formula [1]
However, the partial structural formula in the general formula [1]
Excluding the case where the skeleton is included. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6569795A JP3575104B2 (en) | 1995-03-24 | 1995-03-24 | Hole transport material and its use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6569795A JP3575104B2 (en) | 1995-03-24 | 1995-03-24 | Hole transport material and its use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08259936A JPH08259936A (en) | 1996-10-08 |
| JP3575104B2 true JP3575104B2 (en) | 2004-10-13 |
Family
ID=13294469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6569795A Expired - Fee Related JP3575104B2 (en) | 1995-03-24 | 1995-03-24 | Hole transport material and its use |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3575104B2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2310750A1 (en) * | 1997-11-20 | 1999-06-03 | President And Fellows Of Harvard College | Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment or prevention of diseases characterized by abnormal cell proliferation |
| JP5318367B2 (en) * | 2006-05-10 | 2013-10-16 | 三星ディスプレイ株式會社 | Dimethylenecyclohexane compound, method for producing the same, and organic light-emitting device including the same |
| JP5470750B2 (en) * | 2008-06-06 | 2014-04-16 | コニカミノルタ株式会社 | Amine compound, electrophotographic photoreceptor, image forming apparatus |
| TWI774767B (en) | 2017-05-12 | 2022-08-21 | 瑞士商多蒂孔股份有限公司 | Indane derivatives and their use in organic electronics |
| CN110003090B (en) * | 2019-04-02 | 2021-01-08 | 石家庄诚志永华显示材料有限公司 | Indene derivative and organic electroluminescent device containing indene derivative |
| CN112645916A (en) * | 2020-12-23 | 2021-04-13 | 吉林奥来德光电材料股份有限公司 | Organic light-emitting compound and preparation method and device thereof |
-
1995
- 1995-03-24 JP JP6569795A patent/JP3575104B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08259936A (en) | 1996-10-08 |
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