JP3808139B2 - Electrophotographic photoreceptor - Google Patents
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- JP3808139B2 JP3808139B2 JP23733496A JP23733496A JP3808139B2 JP 3808139 B2 JP3808139 B2 JP 3808139B2 JP 23733496 A JP23733496 A JP 23733496A JP 23733496 A JP23733496 A JP 23733496A JP 3808139 B2 JP3808139 B2 JP 3808139B2
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- 0 *c(c(*(c(cccc1)c1Cl)=O)cc1c2cccc1)c2N=N[C@](CC=C1c(cc2)c3cc2N=NC(C(C(*(c2ccccc2Cl)=O)=C2)=O)=C4C2=CC=CC4)C=C1C3=O Chemical compound *c(c(*(c(cccc1)c1Cl)=O)cc1c2cccc1)c2N=N[C@](CC=C1c(cc2)c3cc2N=NC(C(C(*(c2ccccc2Cl)=O)=C2)=O)=C4C2=CC=CC4)C=C1C3=O 0.000 description 6
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【０００１】
【発明の属する技術分野】
本発明は、電子写真感光体に関し、詳しくは、特定の電荷輸送材料を使用した、光感度、印字特性、繰り返し使用特性に優れた電子写真感光体に関する。
【０００２】
【従来の技術】
有機系の電子写真感光体において、その感度を高めるために電荷発生層と電荷輸送層を積層した機能分離型と呼ばれる感光体が注目され実用化されている。この機能分離型の感光体における静電潜像形成のメカニズムは、感光体を帯電した後、光照射すると、光は電荷発生層により吸収され、光を吸収した電荷発生層は電荷担体を発生し、この電荷担体は電荷輸送層に注入され、帯電によって生じている電界にしたがって電荷輸送層（ないしは感光層）中を移動し、感光体表面の電荷を中和することにより静電潜像を形成するものである。
【０００３】
従来から、種々の感光体材料が開発されているが、これらを実用化できる優れた電子写真感光体にするには、感度、受容電位、電位保持性、電位安定性、残留電位、分光特性に代表される電子写真特性、耐摩耗性等の機械的耐久性、熱、光、放電生成物等に対する化学的安定性等、種々の特性が要求される。とりわけ、高感度で繰り返し安定性に優れたものであることが重要であるが、上述したようにある程度の高感度特性は、適切な電荷発生材料と電荷輸送材料の組合せにより達成することが可能である。一方、これに加えて機械的耐久性を合わせ持つことについての検討もなされているが、従来から提案されている電荷発生材料と電荷輸送材料との組合せによっては上記条件の全てを満たすものは得られていなかった。従って、従来から提案されている電荷発生材料と電荷輸送材料を使用して、高感度を維持し、かつ、繰り返し使用による安定性に優れた電子写真感光体の完成が熱望されていた。
【０００４】
【発明が解決しようとする課題】
本発明の課題は、高感度を失うことなく繰り返し使用によっても優れた安定性を示す電子写真感光体を提供することである。
【０００５】
【課題を解決するための手段】
本発明によれば、以下の発明が提供される。
まず、本発明における、一般式（Ｉ）で示される化合物、一般式（ＩＩ）で示される化合物、一般式（ＩＩＩ）で示される化合物、一般式（ＩＶ）で示される化合物、一般式（Ｖ）で示される化合物、一般式（ＩＶ）で示される化合物、一般式（ＶＩＩ）で示される化合物、一般式（ＶＩＩＩ）で示される化合物及び一般式（ＩＸ）で示される化合物を以下に示す。
【化１】
（１）前記一般式（Ｉ）で示される化合物と前記一般式（ＩＩ）で示される化合物
（２）前記一般式（Ｉ）で示される化合物と前記一般式（ＩＩＩ）で示される化合物
（３）前記一般式（Ｉ）で示される化合物と前記一般式（ＩＶ）で示される化合物
（４）前記一般式（Ｉ）で示される化合物と前記一般式（Ｖ）で示される化合物
（５）前記一般式（Ｉ）で示される化合物と前記一般式（ＶＩ）で示される化合物
（６）前記一般式（Ｉ）で示される化合物と前記一般式（ＶＩＩ）で示される化合物
（７）前記一般式（Ｉ）で示される化合物と前記一般式（ＶＩＩＩ）で示される化合物
（８）前記一般式（Ｉ）で示される化合物と前記一般式（ＩＸ）で示される化合物
（ロ）導電性支持体上に少なくとも電荷発生材料と下記（１）ないし（８）で示される化合物の組から選択される一組を含有する単層感光層を設けてなることを特徴とする電子写真感光体。
（１）前記一般式（Ｉ）で示される化合物と前記一般式（ＩＩ）で示される化合物
（２）前記一般式（Ｉ）で示される化合物と前記一般式（ＩＩＩ）で示される化合物
（３）前記一般式（Ｉ）で示される化合物と前記一般式（ＩＶ）で示される化合物
（４）前記一般式（Ｉ）で示される化合物と前記一般式（Ｖ）で示される化合物
（５）前記一般式（Ｉ）で示される化合物と前記一般式（ＶＩ）で示される化合物
（６）前記一般式（Ｉ）で示される化合物と前記一般式（ＶＩＩ）で示される化合物
（７）前記一般式（Ｉ）で示される化合物と前記一般式（ＶＩＩＩ）で示される化合物
（８）前記一般式（Ｉ）で示される化合物と前記一般式（ＩＸ）で示される化合物。
【０００６】
以下に本発明を詳細に説明する。
本発明者らは上記課題に関して検討を重ねた結果、感光層に上記特定の組合せの電荷輸送材料を用いることにより、繰り返し使用によっても画質欠陥の発生が抑制され、しかも優れた電子写真特性をあわせもつ電子写真感光体が得られることを見出し、本発明に至った。
【０００７】
図面を用いて、本発明の電子写真感光体を説明すると、図１は、本発明における単層感光体を表わす断面図であり、導電性支持体１１上に、感光層１５が設けられている。図２、図３は、本発明における積層感光体の構成例を示す断面図であり、電荷発生材料を主成分とする電荷発生層１７と、電荷輸送材料を主成分とする電荷輸送層１９とが、積層された構成をとっている。
このような単層、または積層感光体において、上述した一般式（Ｉ）示される化合物と一般式（II）ないし（IX）でそれぞれ示される化合物から選択された少なくとも１種とからなる電荷輸送材料が併用して用いられる。
【０００８】
【発明の実施の形態】
以下に発明の実施の形態について述べる。
導電性支持体１１としては、体積抵抗１．０×１０10Ωｃｍ以下の導電性を示すもの、例えば、アルミニウム、ニッケル、クロム、ニクロム、銅、銀、金、白金などの金属、酸化スズ、酸化インジウムなどの金属酸化物を、蒸着またはスパッタリングにより、フィルム状もしくは円筒状のプラスチックもしくは紙に被覆したもの、あるいは、アルミニウム、アルミニウム合金、ニッケル、ステンレス等の板およびそれらを素管化後、切削、超仕上げ、研磨等で表面処理した管等を使用することができる。
【０００９】
次に感光層１５について説明する。説明の都合上、先ず電荷発生層１７と電荷輸送層１９が積層された構成の場合から述べる。
電荷発生層１７は、電荷発生材料を主成分とする層である。電荷発生材料には、無機および有機材料が用いられ、その代表として、モノアゾ顔料、ジスアゾ顔料、トリスアゾ顔料、ペリレン系顔料、ペリノン系顔料、キナクリドン系顔料、キノン系縮合多環化合物、スクアリック酸系染料、フタロシアニン系顔料、ナフタロシアニン系顔料、アズレニウム塩系染料、セレン、セレン−テルル、セレン−ヒ素合金、アモルファス・シリコン等が挙げられる。
【００１０】
電荷発生材料は、単独であるいは、２種以上混合して用いられる。電荷発生層１７は、電荷発生材料を適宜用いられるバインダー樹脂とともに、テトラヒドロフラン、シクロヘキサノン、ジオキサン、２−ブタノン、ジクロルエタン等の適当な溶媒を用いてボールミル、アトライター、サンドミルなどにより分散し、分散液を塗布することにより形成できる。塗布は、浸漬塗工法やスプレーコート、ビードコート法などを用いて行なうことができる。
【００１１】
適宜用いられるバインダー樹脂としては、ポリアミド、ポリウレタン、ポリエステル、エポキシ樹脂、ポリケトン、ポリカーボネート、シリコーン樹脂、アクリル樹脂、ポリビニルブチラール、ポリビニルホルマール、ポリビニルケトン、ポリスチレン、ポリアクリルアミドなどが挙げられ用いられる。適宜用いられるバインダー樹脂の量は、電荷発生材料１重量部に対して０〜２重量部が適当である。
【００１２】
電荷発生層１７は、また、公知の真空薄膜作製法にても設けることができる。電荷発生層１７の膜厚は、０．０１〜５μｍ程度が適当であり、好ましくは０．１〜２μｍである。
【００１３】
電荷輸送層１９は、電荷輸送材料およびバインダー樹脂を適当な溶剤に溶解ないし分散し、これを塗布、乾燥することにより形成できる。また、必要により可塑剤やレべリング剤等を添加することもできる。
【００１４】
電荷輸送材料は、上述した一般式（Ｉ）で示される化合物と一般式（II）ないし（IX）でそれぞれ示される化合物から選択された少なくとも１種とが混合して用いられる。これら化合物の具体例を下記表１および表２ないし表９に挙げる。これら化合物の混合比は、一般式（Ｉ）示される化合物と一般式（II）ないし（IX）でそれぞれ示される化合物から選択された少なくとも１種とが、５：９５〜９５：５の範囲にあると良好な結果が得られる。また、これら電荷輸送材料の使用量は、積層感光体では電荷輸送層の全構成材料に対して１５ないし７５重量％、好ましくは２５ないし６５重量％である。
【００１５】
【表１−（１）】
【表１−（２）】
【表１−（３）】
【表１−（４）】
【表１−（５）】
【表１−（６）】
【表１−（７）】
【表１−（８）】
【表１−（９）】
【表２−（１）】
【表２−（２）】
【表２−（３）】
【表２−（４）】
【表２−（５）】
【表２−（６）】
【表２−（７）】
【表２−（８）】
【表２−（９）】
【表３−（１）】
【表３−（２）】
【表４−（１）】
【表４−（２）】
【表４−（３）】
【表４−（４）】
【表４−（５）】
【表４−（６）】
【表４−（７）】
【表４−（８）】
【表４−（９）】
【表４−（１０）】
【表４−（１１）】
【表４−（１２）】
【表４−（１３）】
【表４−（１４）】
【表４−（１５）】
【表４−（１６）】
【表４−（１７）】
【表４−（１８）】
【表５−（１）】
【表５−（２）】
【表５−（３）】
【表５−（４）】
【表５−（５）】
【表５−（６）】
【表５−（７）】
【表５−（８）】
【表５−（９）】
【表５−（１０）】
【表５−（１１）】
【表５−（１２）】
【表５−（１３）】
【表５−（１４）】
【表５−（１５）】
【表５−（１６）】
【表５−（１７）】
【表５−（１８）】
【表５−（１９）】
【表５−（２０）】
【表５−（２１）】
【表５−（２２）】
【表５−（２３）】
【表５−（２４）】
【表５−（２５）】
【表５−（２６）】
【表５−（２７）】
【表５−（２８）】
【表５−（２９）】
【表５−（３０）】
【表５−（３１）】
【表５−（３２）】
【表５−（３３）】
【表５−（３４）】
【表５−（３５）】
【表５−（３６）】
【表５−（３７）】
【表５−（３８）】
【表５−（３９）】
【表５−（４０）】
【表５−（４１）】
【表５−（４２）】
【表５−（４３）】
【表６−（１）】
【表６−（２）】
【表６−（３）】
【表６−（４）】
【表７−（１）】
【表７−（２）】
【表８−（１）】
【表８−（２）】
【表８−（３）】
【表８−（４）】
【表９−（１）】
【表９−（２）】
【表９−（３）】
【表９−（４）】
また、一般式（Ｉ）で示される化合物と一般式（II）ないし（IX）でそれぞれ示される化合物から選択された少なくとも１種とからなる電荷輸送材料のほかに、さらに公知の電子輸送性電荷輸送材料および／または正孔輸送性電荷輸送材料を併用してもよい。
【０１１１】
電荷輸送材料とともに電荷輸送層１９に使用されるバインダー樹脂としては、ポリスチレン、スチレン−アクリロニトリル共重合体、スチレン−ブタジエン共重合体、スチレン−無水マレイン酸共重合体、ポリエステル、ポリ塩化ビニル、塩化ビニル−酢酸ビニル共重合体、ポリ酢酸ビニル、ポリ塩化ビニリデン、ポリアリレート、フェノキシ樹脂、ポリカーボネート、酢酸セルロース樹脂、エチルセルロース樹脂、ポリビニルブチラール、ポリビニルホルマール、ポリビニルトルエン、アクリル樹脂、シリコーン樹脂、エポキシ樹脂、メラミン樹脂、ウレタン樹脂、フェノール樹脂、アルキッド樹脂等の熱可塑性、または熱硬化性樹脂が挙げられる。
【０１１２】
溶剤としては、テトラヒドロフラン、ジオキサン、トルエン、２−ブタノン、モノクロルベンゼン、ジクロルエタン、塩化メチレンなどが用いられる。
【０１１３】
電荷輸送層１９の厚さは、５〜１００μｍが適当である。
【０１１４】
本発明において、電荷輸送層１９中に可塑剤やレべリング剤を添加してもよい。可塑剤としては、ジブチルフタレート、ジオクチルフタレートなど一般の樹脂の可塑剤として使用されているものがそのまま使用でき、その使用量は、バインダー樹脂に対して０〜３０重量％程度が適当である。レベリング剤としては、ジメチルシリコーンオイル、メチルフェニルシリコーンオイルなどのシリコーンオイル類や、側鎖にパーフルオロアルキル基を有するポリマーあるいはオリゴマーが使用され、その使用量はバインダー樹脂に対して、０〜１重量％が適当である。
【０１１５】
次に感光層１５が単層構成の場合について述べる。この場合に用いられる材料も多くは電荷発生材料と電荷輸送材料よりなる機能分離型で用いられるものと同じものが挙げられる。
【０１１６】
即ち、少なくとも電荷発生材料および一般式（Ｉ）で示される化合物と一般式（II）ないし（IX）でそれぞれ示される化合物から選択された少なくとも１種とからなる電荷輸送材料を、バインダー樹脂とともに適当な溶剤に溶解ないし分散し、これを塗布、乾燥することによって形成できる。また、必要により可塑剤やしべリング剤等を添加することもできる。
バインダー樹脂としては、先に電荷輸送層１９で挙げたバインダー樹脂をそのまま用いることができるほかに、電荷発生層１７で挙げたバインダー樹脂を混合してもよい。
【０１１７】
ピリリウム系染料、ビスフェノールＡ系ポリカーボネートから形成される共晶錯体に一般式（Ｉ）で示される化合物と一般式（II）ないし（IX）でそれぞれ示される化合物から選択された少なくとも１種とからなる電荷輸送材料を添加した感光層も単層感光層として用いることができる。
【０１１８】
さらに、一般式（Ｉ）で示される化合物と一般式（II）ないし（IX）でそれぞれ示される化合物から選択された少なくとも１種とからなる電荷輸送材料およびバインダー樹脂を主成分としてなり、電荷発生材料を有効成分として含まない単層感光層も青色光〜紫外光に感度を有する感光体として有用である。
【０１１９】
単層感光層における上記特定の２種類の電荷輸送材料の混合比は、積層感光層の場合と同様、５：９５〜９５：５の範囲が好ましく、その使用量は単層感光層の全構成材料に対して５ないし７５重量％、好ましくは１０〜６５重量％である。また、単層感光層の膜厚は５〜１００μｍが適当である。
【０１２０】
本発明の電子写真感光体には、導電性支持体１１と感光層との間に下引き層を設けることができる。下引き層は一般に樹脂を主成分とするが、これらの樹脂はその上に感光層を溶剤でもって塗布することを考えると、一般の有機溶剤に対して耐溶解性の高い樹脂であることが望ましい。このような樹脂としては、ポリビニルアルコール、カゼイン、ポリアクリル酸ナトリウム等の水溶性樹脂、共重合ナイロン、メトキシメチル化ナイロン等のアルコール可溶性樹脂、ポリウレタン、メラミン樹脂、アルキッド−メラミン樹脂、エポキシ樹脂等、三次元網目構造を形成する硬化型樹脂などが挙げられる。
【０１２１】
また、下引き層にはモアレ防止、残留電位の低減等のために酸化チタン、シリカ、アルミナ、酸化ジルコニウム、酸化スズ、酸化インジウム等で例示できる金属酸化物の微粉末を加えてもよい。これらの下引き層は、前述の感光層のごとく適当な溶媒、塗工法を用いて形成することができる。
【０１２２】
更に本発明の下引き層として、シランカップリング剤、チタンカップリング剤、クロムカップリング剤等を使用して、例えばゾル−ゲル法等により形成した金属酸化物層も有用である。
【０１２３】
この他に、本発明の下引き層にはＡｌ2Ｏ3を陽極酸化にて設けたものや、ポリパラキシリレン（パリレン）等の有機物や、ＳｉＯ、ＳｎＯ2、ＴｉＯ2、ＩＴＯ、ＣｅＯ2等の無機物を真空薄膜作製法にて設けたものも良好に使用できる。下引き層の膜厚は０〜５μｍが適当である。
【０１２４】
本発明の電子写真感光体には、感光層保護の目的で、保護層が感光層の上に設けられることもある。これに使用される材料としては、ＡＢＳ樹脂、ＡＣＳ樹脂、オレフィン〜ビニルモノマー共重合体、塩素化ポリエーテル、アリル樹脂、フェノール樹脂、ポリアセタール、ポリアミド、ポリアミドイミド、ポリアクリレート、ポリアリルスルホン、ポリブチレン、ポリブチレンテレフタレート、ポリカーボネート、ポリエーテルスルホン、ポリエチレン、ポリエチレンテレフタレート、ポリイミド、アクリル樹脂、ポリメチルペンテン、ポリプロピレン、ポリフェニレンオキシド、ポリスルホン、ＡＳ樹脂、ＡＢ樹脂、ＢＳ樹脂、ポリウレタン、ポリ塩化ビニル、ポリ塩化ビニリデン、エポキシ樹脂等の樹脂が挙げられる。
【０１２５】
保護層にはその他、耐摩耗性を向上する目的で、ポリテトラフルオロエチレンのようなフッ素樹脂、シリコーン樹脂およびこれら樹脂に酸化チタン、酸化スズ、チタン酸カリウム等の無機材料を分散したもの等を添加することができる。
保護層の形成法としては、通常の塗布法が採用される。なお、保護層の厚さは、０．５〜１０μｍ程度が適当である。また、以上のほかに真空薄膜作製法にて形成したｉ−Ｃ，ａ−ＳｉＣなど公知の材料も保護層として用いることができる。
【０１２６】
本発明においては、感光層と保護層との間に別の中間層を設けることも可能である。中間層には、一般にバインダー樹脂を主成分として用いる。これら樹脂としては、ポリアミド、アルコール可溶性ナイロン、水溶性ポリビニルブチラール、ポリビニルブチラール、ポリビニルアルコールなどが挙げられる。
中間層の形成法としては、前述のごとく通常の塗布法が採用される。なお、中間層の厚さは０．０５〜２μｍ程度が適当である。
【０１２７】
【実施例】
次に実施例を示すが、実施例は本発明を詳しく説明するものであり、本発明が実施例によって制約されるものではない。なお、実施例中の部はすべて重量部である。
先ず電荷輸送材料として一般式（Ｉ）および一般式（II）で示される化合物を併用した場合について、実施例１から８および比較例１から８により説明する。
【０１２８】
〔実施例１〕
外径７０ｍｍのアルミニウムシリンダー上に、下記組成の下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を順次、塗布・乾燥して各々４μｍの下引層、０．２μｍの電荷発生層、２２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０１２９】
〔電荷輸送層塗工液〕
化合物ＮＯ．II−１の化合物 ３部
化合物ＮＯ．Ｉ−２の化合物 ６部
ポリカーボネート（帝人化成社製：パンライトＫ−１３００） １０部
テトラヒドロフラン ７５部
【０１３２】
〔比較例１〕
実施例１の電荷輸送層塗工液を下記組成のものに変えた以外は実施例１と同様にして比較例の電子写真感光体を作製した。
【０１３３】
〔実施例２〕
アルミニウムシリンダー表面を陽極酸化処理した後、封孔処理を行った。この上に、下記電荷発生層塗工液、電荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの電荷発生層、２０μｍの電荷輸送層を形成し本発明の電子写真感光体を作製した。
【０１３５】
〔比較例２〕
実施例２の電荷輸送層塗工液において、化合物ＮＯ．II−６の化合物を添加しないこと以外は実施例２と同様にして比較例の電子写真感光体を作製した。
【０１３８】
〔実施例３〕
アルミニウムシリンダー上に、下記組成の下引層塗工液、下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗工液を、順次塗布・乾燥して各々２μｍの下引層、０．２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０１３９】
〔電荷発生層塗工液〕
下記構造式（化１３）の電荷発生材料 ３部
【化１３】
シクロヘキサノン １５０部
４−メチル−２−ペンタノン １００部
【０１４１】
〔比較例３〕
実施例３の電荷輸送層塗工液を下記組成のものにした以外は実施例３と同様にして比較例の電子写真感光体を作製した。
【０１４３】
〔実施例４〕
実施例１の電荷輸送層塗工液を下記組成のものにした以外は実施例１と同様にして本発明の電子写真感光体を作製した。
【０１４５】
〔比較例４〕
実施例４の電荷輸送層塗工液を下記組成のものにした以外は実施例４と同様にして比較例の電子写真感光体を作製した。
【０１４７】
〔実施例５〕
実施例２の電荷輸送層塗工液を下記組成のものにした以外は実施例２と同様にして本発明の電子写真感光体を作製した。
【０１４９】
〔電荷輸送層塗工液〕
化合物ＮＯ．II−３５の化合物 ２部
化合物ＮＯ．Ｉ−４４の化合物 ７部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０１５０】
〔比較例５〕
実施例５の電荷輸送層塗工液を下記組成のものにした以外は実施例５と同様にして比較例の電子写真感光体を作製した。
【０１５１】
〔電荷輸送層塗工液〕
化合物ＮＯ．II−３５の化合物 ９部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０１５２】
〔実施例６〕
実施例３の電荷輸送層塗工液を下記組成のものにした以外は実施例３と同様にして本発明の電子写真感光体を作製した。
【０１５３】
〔比較例６〕
実施例６の電荷輸送層塗工液において、化合物ＮＯ．Ｉ−４７の化合物を添加しないこと以外は実施例６と同様にして比較例の電子写真感光体を作製した。
【０１５５】
〔実施例７〕
アルミニウムシリンダー上に、下記組成の共晶錯体光導電層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導電層を形成し本発明の電子写真感光体を作製した。
【０１５６】
〔比較例７〕
実施例７の電荷輸送層塗工液において、化合物ＮＯ．II−４８の化合物を添加しないこと以外は実施例７と同様にして比較例の電子写真感光体を作製した。
【０１５８】
〔実施例８〕
アルミニウムシリンダー上に、下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発明の電子写真感光体を作製した。
【０１５９】
〔比較例８〕
アルミニウムシリンダー上に、下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較例の電子写真感光体を作製した。
【０１６１】
以上の実施例及び比較例の各感光体を特開昭６０−１００１６７号公報に開示されている評価装置を用いて次のような測定を行なった。コロナ放電電圧−６．０ｋＶ（または＋５．６ｋＶ）で帯電２０秒後の電位Ｖｍ（Ｖ）、暗減衰２０秒後の電位Ｖｏ（Ｖ）、強度６ｌｕｘの白色光による露光２０秒後の残留電位ＶＲ（Ｖ）、更に電位Ｖｏを１／２に減衰させるのに必要な露光量Ｅ1/2［ｌｕｘ・ｓｅｃ］を測定した。電位保持率＝Ｖｏ／Ｖｍと定義する。
また、各感光体をリコー製複写機ＦＴ−３３００（ないしは感光体を正帯電できるように改造したもの）に搭載して連続３万枚の複写を行い、異常画像の有無を目視により判定した。また、複写試験終了後の各感光体は、上記と同じ方法で感光体特性を測定した。試験結果を表１０に示す。
【０１６３】
【表１０】
次に電荷輸送材料として一般式（Ｉ）で示される化合物と一般式（III）で示される化合物を併用した場合について、実施例９から１６および比較例９から１６により説明する。
【０１６５】
〔実施例９〕
外径７０ｍｍのアルミニウムシリンダー上に、下記組成の下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を順次、塗布・乾燥して各々４μｍの下引層、０．２μｍの電荷発生層、２２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０１６６】
〔電荷輸送層塗工液〕
化合物ＮＯ．III−８の化合物 ３部
化合物ＮＯ．Ｉ−２の化合物 ６部
ポリカーボネート（帝人化成社製：パンライトＫ−１３００） １０部
テトラヒドロフラン ７５部
【０１６９】
〔比較例９〕
実施例９の電荷輸送層塗工液を下記組成のものに変えた以外は実施例９と同様にして比較例の電子写真感光体を作製した。
【０１７０】
〔実施例１０〕
アルミニウムシリンダー表面を陽極酸化処理した後、封孔処理を行った。この上に、下記電荷発生層塗工液、電荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの電荷発生層、２０μｍの電荷輸送層を形成し本発明の電子写真感光体を作製した。
【０１７２】
〔比較例１０〕
実施例１０の電荷輸送層塗工液において、化合物ＮＯ．III−１０の化合物を添加しないこと以外は実施例１０と同様にして比較例の電子写真感光体を作製した。
【０１７５】
〔実施例１１〕
アルミニウムシリンダー上に、下記組成の下引層塗工液、下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗工液を、順次塗布・乾燥して各々２μｍの下引層、０．２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０１７６】
〔電荷発生層塗工液〕
下記構造式（化１３）の電荷発生材料 ３部
【化１３】
シクロヘキサノン １５０部
４−メチル−２−ペンタノン １００部
【０１７８】
〔比較例１１〕
実施例１１の電荷輸送層塗工液を下記組成のものにした以外は実施例１１と同様にして比較例の電子写真感光体を作製した。
【０１８０】
〔実施例１２〕
実施例９の電荷輸送層塗工液を下記組成のものにした以外は実施例９と同様にして本発明の電子写真感光体を作製した。
【０１８２】
〔比較例１２〕
実施例１２の電荷輸送層塗工液を下記組成のものにした以外は実施例１２と同様にして比較例の電子写真感光体を作製した。
【０１８４】
〔実施例１３〕
実施例１０の電荷輸送層塗工液を下記組成のものにした以外は実施例１０と同様にして本発明の電子写真感光体を作製した。
【０１８６】
〔電荷輸送層塗工液〕
化合物ＮＯ．III−１７の化合物 ２部
化合物ＮＯ．Ｉ−４４の化合物 ７部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０１８７】
〔比較例１３〕
実施例１３の電荷輸送層塗工液を下記組成のものにした以外は実施例１３と同様にして比較例の電子写真感光体を作製した。
【０１８８】
〔電荷輸送層塗工液〕
化合物ＮＯ．III−１７の化合物 ９部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０１８９】
〔実施例１４〕
実施例１１の電荷輸送層塗工液を下記組成のものにした以外は実施例１１と同様にして本発明の電子写真感光体を作製した。
【０１９０】
〔比較例１４〕
実施例１４の電荷輸送層塗工液において、化合物ＮＯ．Ｉ−４７の化合物を添加しないこと以外は実施例１４と同様にして比較例の電子写真感光体を作製した。
【０１９２】
〔実施例１５〕
アルミニウムシリンダー上に、下記組成の共晶錯体光導電層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導電層を形成し本発明の電子写真感光体を作製した。
【０１９３】
〔比較例１５〕
実施例１５の電荷輸送層塗工液において、化合物ＮＯ．III−２０の化合物を添加しないこと以外は実施例１５と同様にして比較例の電子写真感光体を作製した。
【０１９５】
〔実施例１６〕
アルミニウムシリンダー上に、下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発明の電子写真感光体を作製した。
【０１９６】
〔比較例１６〕
アルミニウムシリンダー上に、下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較例の電子写真感光体を作製した。
【０１９８】
実施例９から１６および比較例９から１６で得られた各感光体について、前記と同様の方法で感光体特性を測定した。結果を表１１に示す。
【０２００】
【表１１】
次に電荷輸送材料として一般式（Ｉ）で示される化合物と一般式（IV）で示される化合物を併用した場合について、実施例１７から２４および比較例１７から２４により説明する。
【０２０２】
〔実施例１７〕
外径７０ｍｍのアルミニウムシリンダー上に、下記組成の下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を順次、塗布・乾燥して各々４μｍの下引層、０．２μｍの電荷発生層、２２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０２０３】
〔電荷輸送層塗工液〕
化合物ＮＯ．IV−２の化合物 ３部
化合物ＮＯ．Ｉ−２の化合物 ６部
ポリカーボネート（帝人化成社製：パンライトＫ−１３００） １０部
テトラヒドロフラン ７５部
【０２０６】
〔比較例１７〕
実施例１７の電荷輸送層塗工液を下記組成のものに変えた以外は実施例１７と同様にして比較例の電子写真感光体を作製した。
【０２０７】
〔実施例１８〕
アルミニウムシリンダー表面を陽極酸化処理した後、封孔処理を行った。この上に、下記電荷発生層塗工液、電荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの電荷発生層、２０μｍの電荷輸送層を形成し本発明の電子写真感光体を作製した。
【０２０９】
〔比較例１８〕
実施例１８の電荷輸送層塗工液において、化合物ＮＯ．IV−１４の化合物を添加しないこと以外は実施例１８と同様にして比較例の電子写真感光体を作製した。
【０２１２】
〔実施例１９〕
アルミニウムシリンダー上に、下記組成の下引層塗工液、下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗工液を、順次塗布・乾燥して各々２μｍの下引層、０．２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０２１３】
〔電荷発生層塗工液〕
下記構造式（化１３）の電荷発生材料 ３部
【化１３】
シクロヘキサノン １５０部
４−メチル−２−ペンタノン １００部
【０２１５】
〔比較例１９〕
実施例１９の電荷輸送層塗工液を下記組成のものにした以外は実施例１９と同様にして比較例の電子写真感光体を作製した。
【０２１７】
〔実施例２０〕
実施例１７の電荷輸送層塗工液を下記組成のものにした以外は実施例１７と同様にして本発明の電子写真感光体を作製した。
【０２１９】
〔比較例２０〕
実施例２０の電荷輸送層塗工液を下記組成のものにした以外は実施例２０と同様にして比較例の電子写真感光体を作製した。
【０２２１】
〔実施例２１〕
実施例１８の電荷輸送層塗工液を下記組成のものにした以外は実施例１８と同様にして本発明の電子写真感光体を作製した。
【０２２３】
〔電荷輸送層塗工液〕
化合物ＮＯ．IV−５１の化合物 ２部
化合物ＮＯ．I−４４の化合物 ７部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０２２４】
〔比較例２１〕
実施例２１の電荷輸送層塗工液を下記組成のものにした以外は実施例２１と同様にして比較例の電子写真感光体を作製した。
【０２２５】
〔電荷輸送層塗工液〕
化合物ＮＯ．IV−５１の化合物 ９部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０２２６】
〔実施例２２〕
実施例１９の電荷輸送層塗工液を下記組成のものにした以外は実施例１９と同様にして本発明の電子写真感光体を作製した。
【０２２７】
〔比較例２２〕
実施例２２の電荷輸送層塗工液において、化合物ＮＯ．I−４７の化合物を添加しないこと以外は実施例２２と同様にして比較例の電子写真感光体を作製した。
【０２２９】
〔実施例２３〕
アルミニウムシリンダー上に、下記組成の共晶錯体光導電層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導電層を形成し本発明の電子写真感光体を作製した。
【０２３０】
〔比較例２３〕
実施例２３の電荷輸送層塗工液において、化合物ＮＯ．IV−９８の化合物を添加しないこと以外は実施例２３と同様にして比較例の電子写真感光体を作製した。
【０２３２】
〔実施例２４〕
アルミニウムシリンダー上に、下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発明の電子写真感光体を作製した。
【０２３３】
〔比較例２４〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較例の電子写真感光体を作製した。
【０２３５】
上記実施例１７から２４および比較例１７から２４で得られた各感光体について上記と同様の方法で感光体特性を測定した。結果を表１２に示す。
【０２３７】
【表１２】
次に電荷輸送材料として一般式（Ｉ）で示される化合物と一般式（Ｖ）で示される化合物を併用した場合について、実施例２５から３２および比較例２５から３２により説明する。
【０２３９】
〔実施例２５〕
外径７０ｍｍのアルミニウムシリンダー上に下記組成の下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を順次、塗布・乾燥して各々４μｍの下引層、０．２μｍの電荷発生層、２２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０２４０】
〔電荷輸送層塗工液〕
化合物ＮＯ．V−９の化合物 ３部
化合物ＮＯ．I−２の化合物 ６部
ポリカーボネート（帝人化成社製：パンライトＫ−１３００） １０部
テトラヒドロフラン ７５部
【０２４３】
〔比較例２５〕
実施例２５の電荷輸送層塗工液を下記組成のものに変えた以外は実施例２５と同様にして比較例の電子写真感光体を作製した。
【０２４４】
〔実施例２６〕
アルミニウムシリンダー表面を陽極酸化処理した後、封孔処理を行った。この上に、下記電荷発生層塗工液、電荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの電荷発生層、２０μｍの電荷輸送層を形成し本発明の電子写真感光体を作製した。
【０２４６】
〔比較例２６〕
実施例２６の電荷輸送層塗工液において、化合物ＮＯ．V−１９の化合物を添加しないこと以外は実施例２６と同様にして比較例の電子写真感光体を作製した。
【０２４９】
〔実施例２７〕
アルミニウムシリンダー上に下記組成の下引層塗工液、下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗工液を、順次塗布・乾燥して各々２μｍの下引層、０．２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０２５０】
〔電荷発生層塗工液〕
下記構造式（化１３）の電荷発生材料 ３部
【化１３】
シクロヘキサノン １５０部
４−メチル−２−ペンタノン １００部
【０２５２】
〔比較例２７〕
実施例２７の電荷輸送層塗工液を下記組成のものにした以外は実施例２７と同様にして比較例の電子写真感光体を作製した。
【０２５４】
〔実施例２８〕
実施例２５の電荷輸送層塗工液を下記組成のものにした以外は実施例２５と同様にして本発明の電子写真感光体を作製した。
【０２５６】
〔比較例２８〕
実施例２８の電荷輸送層塗工液を下記組成のものにした以外は実施例２８と同様にして比較例の電子写真感光体を作製した。
【０２５８】
〔実施例２９〕
実施例２６の電荷輸送層塗工液を下記組成のものにした以外は実施例２６と同様にして本発明の電子写真感光体を作製した。
【０２６０】
〔電荷輸送層塗工液〕
化合物ＮＯ．V−８１の化合物 ２部
化合物ＮＯ．I−４４の化合物 ７部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０２６１】
〔比較例２９〕
実施例２９の電荷輸送層塗工液を下記組成のものにした以外は実施例２９と同様にして比較例の電子写真感光体を作製した。
【０２６２】
〔電荷輸送層塗工液〕
化合物ＮＯ．V−８１の化合物 ９部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０２６３】
〔実施例３０〕
実施例２７の電荷輸送層塗工液を下記組成のものにした以外は実施例２７と同様にして本発明の電子写真感光体を作製した。
〔比較例３０〕
実施例３０の電荷輸送層塗工液において、化合物ＮＯ．I−４７の化合物を添加しないこと以外は実施例３０と同様にして比較例の電子写真感光体を作製した。
【０２６５】
〔実施例３１〕
アルミニウムシリンダー上に下記組成の共晶錯体光導電層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導電層を形成し本発明の電子写真感光体を作製した。
【０２６６】
〔比較例３１〕
実施例３１の電荷輸送層塗工液において、化合物ＮＯ．V−１１６の化合物を添加しないこと以外は実施例３１と同様にして比較例の電子写真感光体を作製した。
【０２６８】
〔実施例３２〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発明の電子写真感光体を作製した。
【０２６９】
〔比較例３２〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較例の電子写真感光体を作製した。
【０２７１】
上記実施例２５から３２および比較例２５から３２で得られた各感光体について上記と同様の方法で感光体特性を測定した。結果を表１３に示す。
【０２７３】
【表１３】
次に電荷輸送材料として一般式（Ｉ）で示される化合物と一般式（VI）で示される化合物を併用した場合について、実施例３３から４０および比較例３３から４０により説明する。
【０２７５】
〔実施例３３〕
外径７０ｍｍのアルミニウムシリンダー上に下記組成の下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を順次、塗布・乾燥して各々４μｍの下引層、０．２μｍの電荷発生層、２２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０２７６】
〔電荷輸送層塗工液〕
化合物ＮＯ．VI−３の化合物 ３部
化合物ＮＯ．I−２の化合物 ６部
ポリカーボネート（帝人化成社製：パンライトＫ−１３００） １０部
テトラヒドロフラン ７５部
【０２７９】
〔比較例３３〕
実施例３３の電荷輸送層塗工液を下記組成のものに変えた以外は実施例３３と同様にして比較例の電子写真感光体を作製した。
【０２８０】
〔実施例３４〕
アルミニウムシリンダー表面を陽極酸化処理した後、封孔処理を行った。この上に、下記電荷発生層塗工液、電荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの電荷発生層、２０μｍの電荷輸送層を形成し本発明の電子写真感光体を作製した。
【０２８２】
〔比較例３４〕
実施例３４の電荷輸送層塗工液において、化合物ＮＯ．VI−６の化合物を添加しないこと以外は実施例３４と同様にして比較例の電子写真感光体を作製した。
【０２８５】
〔実施例３５〕
アルミニウムシリンダー上に下記組成の下引層塗工液、下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗工液を、順次塗布・乾燥して各々２μｍの下引層、０．２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０２８６】
〔電荷発生層塗工液〕
下記構造式（化１３）の電荷発生材料 ３部
【化１３】
シクロヘキサノン １５０部
４−メチル−２−ペンタノン １００部
【０２８８】
〔比較例３５〕
実施例３５の電荷輸送層塗工液を下記組成のものにした以外は実施例３５と同様にして比較例の電子写真感光体を作製した。
【０２９０】
〔実施例３６〕
実施例３３の電荷輸送層塗工液を下記組成のものにした以外は実施例３３と同様にして本発明の電子写真感光体を作製した。
【０２９２】
〔比較例３６〕
実施例３６の電荷輸送層塗工液を下記組成のものにした以外は実施例３６と同様にして比較例の電子写真感光体を作製した。
【０２９４】
〔実施例３７〕
実施例３４の電荷輸送層塗工液を下記組成のものにした以外は実施例３４と同様にして本発明の電子写真感光体を作製した。
【０２９６】
〔電荷輸送層塗工液〕
化合物ＮＯ．VI−１３の化合物 ２部
化合物ＮＯ．I−４４の化合物 ７部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０２９７】
〔比較例３７〕
実施例３７の電荷輸送層塗工液を下記組成のものにした以外は実施例３７と同様にして比較例の電子写真感光体を作製した。
【０２９８】
〔電荷輸送層塗工液〕
化合物ＮＯ．VI−１３の化合物 ９部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０２９９】
〔実施例３８〕
実施例３５の電荷輸送層塗工液を下記組成のものにした以外は実施例３５と同様にして本発明の電子写真感光体を作製した。
【０３００】
〔比較例３８〕
実施例３８の電荷輸送層塗工液において、化合物ＮＯ．I−４７の化合物を添加しないこと以外は実施例３８と同様にして比較例の電子写真感光体を作製した。
【０３０２】
〔実施例３９〕
アルミニウムシリンダー上に下記組成の共晶錯体光導電層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導電層を形成し本発明の電子写真感光体を作製した。
【０３０３】
〔比較例３９〕
実施例３９の電荷輸送層塗工液において、化合物ＮＯ．VI−９の化合物を添加しないこと以外は実施例３９と同様にして比較例の電子写真感光体を作製した。
【０３０５】
〔実施例４０〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発明の電子写真感光体を作製した。
【０３０６】
〔感光層塗工液〕下記構造式（化１４）の電荷発生材料 ３部
【化１４】
〔比較例４０〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較例の電子写真感光体を作製した。
【０３０８】
上記実施例３３から４０および比較例３３から４０で得られた各感光体について上記と同様の方法で感光体特性を測定した。結果を表１４に示す。
【０３１０】
【表１４】
次に電荷輸送材料として一般式（Ｉ）で示される化合物と一般式（VII）で示される化合物を併用した場合について、実施例４１から４８および比較例４１から４８により説明する。
【０３１２】
〔実施例４１〕
外径７０ｍｍのアルミニウムシリンダー上に下記組成の下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を順次、塗布・乾燥して各々４μｍの下引層、０．２μｍの電荷発生層、２２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０３１３】
〔電荷輸送層塗工液〕
化合物ＮＯ．VII−１の化合物 ３部
化合物ＮＯ．I−２の化合物 ６部
ポリカーボネート（帝人化成社製：パンライトＫ−１３００） １０部
テトラヒドロフラン ７５部
【０３１６】
〔比較例４１〕
実施例４１の電荷輸送層塗工液を下記組成のものに変えた以外は実施例４１と同様にして比較例の電子写真感光体を作製した。
【０３１７】
〔実施例４２〕
アルミニウムシリンダー表面を陽極酸化処理した後、封孔処理を行った。この上に、下記電荷発生層塗工液、電荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの電荷発生層、２０μｍの電荷輸送層を形成し本発明の電子写真感光体を作製した。
【０３１９】
〔比較例４２〕
実施例４２の電荷輸送層塗工液において、化合物ＮＯ．VII−３の化合物を添加しないこと以外は実施例４２と同様にして比較例の電子写真感光体を作製した。
【０３２２】
〔実施例４３〕
アルミニウムシリンダー上に下記組成の下引層塗工液、下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗工液を、順次塗布・乾燥して各々２μｍの下引層、０．２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０３２３】
〔電荷発生層塗工液〕
下記構造式（化１３）の電荷発生材料 ３部
【化１３】
シクロヘキサノン １５０部
４−メチル−２−ペンタノン １００部
【０３２５】
〔比較例４３〕
実施例４３の電荷輸送層塗工液を下記組成のものにした以外は実施例４３と同様にして比較例の電子写真感光体を作製した。
【０３２７】
〔実施例４４〕
実施例４１の電荷輸送層塗工液を下記組成のものにした以外は実施例４１と同様にして本発明の電子写真感光体を作製した。
【０３２９】
〔比較例４４〕
実施例４４の電荷輸送層塗工液を下記組成のものにした以外は実施例４４と同様にして比較例の電子写真感光体を作製した。
【０３３１】
〔実施例４５〕
実施例４２の電荷輸送層塗工液を下記組成のものにした以外は実施例４２と同様にして本発明の電子写真感光体を作製した。
【０３３３】
〔電荷輸送層塗工液〕
化合物ＮＯ．VII−１１の化合物 ２部
化合物ＮＯ．I−４４の化合物 ７部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０３３４】
〔比較例４５〕
実施例４５の電荷輸送層塗工液を下記組成のものにした以外は実施例４５と同様にして比較例の電子写真感光体を作製した。
【０３３５】
〔電荷輸送層塗工液〕
化合物ＮＯ．VII−１１の化合物 ９部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０３３６】
〔実施例４６〕
実施例４３の電荷輸送層塗工液を下記組成のものにした以外は実施例４３と同様にして本発明の電子写真感光体を作製した。
【０３３７】
〔比較例４６〕
実施例４６の電荷輸送層塗工液において、化合物ＮＯ．I−４７の化合物を添加しないこと以外は実施例４６と同様にして比較例の電子写真感光体を作製した。
【０３３９】
〔実施例４７〕
アルミニウムシリンダー上に下記組成の共晶錯体光導電層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導電層を形成し本発明の電子写真感光体を作製した。
【０３４０】
〔比較例４７〕
実施例４７の電荷輸送層塗工液において、化合物ＮＯ．VII−２の化合物を添加しないこと以外は実施例４７と同様にして比較例の電子写真感光体を作製した。
【０３４２】
〔実施例４８〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発明の電子写真感光体を作製した。
【０３４３】
〔比較例４８〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較例の電子写真感光体を作製した。
【０３４５】
上記実施例４１から４８および比較例４１から４８で得られた各感光体について前記と同様の方法で感光体特性を測定した。結果を表１５に示す。
【０３４７】
【表１５】
次に電荷輸送材料として一般式（Ｉ）で示される化合物と一般式（VIII）で示される化合物を併用した場合について、実施例４９から５６および比較例４９から５６により説明する。
【０３４９】
〔実施例４９〕
外径７０ｍｍのアルミニウムシリンダー上に下記組成の下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を順次、塗布・乾燥して各々４μｍの下引層、０．２μｍの電荷発生層、２２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０３５０】
〔電荷輸送層塗工液〕
化合物ＮＯ．VIII−１１の化合物 ３部
化合物ＮＯ．I−２の化合物 ６部
ポリカーボネート（帝人化成社製：パンライトＫ−１３００） １０部
テトラヒドロフラン ７５部
【０３５３】
〔比較例４９〕
実施例４９の電荷輸送層塗工液を下記組成のものに変えた以外は実施例４９と同様にして比較例の電子写真感光体を作製した。
【０３５４】
〔実施例５０〕
アルミニウムシリンダー表面を陽極酸化処理した後、封孔処理を行った。この上に、下記電荷発生層塗工液、電荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの電荷発生層、２０μｍの電荷輸送層を形成し本発明の電子写真感光体を作製した。
【０３５６】
〔比較例５０〕
実施例５０の電荷輸送層塗工液において、化合物ＮＯ．VIII−１６の化合物を添加しないこと以外は実施例５０と同様にして比較例の電子写真感光体を作製した。
【０３５９】
〔実施例５１〕
アルミニウムシリンダー上に下記組成の下引層塗工液、下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗工液を、順次塗布・乾燥して各々２μｍの下引層、０．２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０３６０】
〔電荷発生層塗工液〕
下記構造式（化１３）の電荷発生材料 ３部
【化１３】
シクロヘキサノン １５０部
４−メチル−２−ペンタノン １００部
【０３６２】
〔比較例５１〕
実施例５１の電荷輸送層塗工液を下記組成のものにした以外は実施例５１と同様にして比較例の電子写真感光体を作製した。
【０３６４】
〔実施例５２〕
実施例４９の電荷輸送層塗工液を下記組成のものにした以外は実施例４９と同様にして本発明の電子写真感光体を作製した。
【０３６６】
〔比較例５２〕
実施例５２の電荷輸送層塗工液を下記組成のものにした以外は実施例５２と同様にして比較例の電子写真感光体を作製した。
【０３６８】
〔実施例５３〕
実施例５０の電荷輸送層塗工液を下記組成のものにした以外は実施例５０と同様にして本発明の電子写真感光体を作製した。
【０３７０】
〔電荷輸送層塗工液〕
化合物ＮＯ．VIII−１４の化合物 ２部
化合物ＮＯ．I−４４の化合物 ７部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０３７１】
〔比較例５３〕
実施例５３の電荷輸送層塗工液を下記組成のものにした以外は実施例５３と同様にして比較例の電子写真感光体を作製した。
【０３７２】
〔電荷輸送層塗工液〕
化合物ＮＯ．VIII−１４の化合物 ９部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０３７３】
〔実施例５４〕
実施例５１の電荷輸送層塗工液を下記組成のものにした以外は実施例５１と同様にして本発明の電子写真感光体を作製した。
【０３７４】
〔比較例５４〕
実施例５４の電荷輸送層塗工液において、化合物ＮＯ．I−４７の化合物を添加しないこと以外は実施例５４と同様にして比較例の電子写真感光体を作製した。
【０３７６】
〔実施例５５〕
アルミニウムシリンダー上に下記組成の共晶錯体光導電層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導電層を形成し本発明の電子写真感光体を作製した。
【０３７７】
〔比較例５５〕
実施例５５の電荷輸送層塗工液において、化合物ＮＯ．VIII−４６の化合物を添加しないこと以外は実施例５５と同様にして比較例の電子写真感光体を作製した。
【０３７９】
〔実施例５６〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発明の電子写真感光体を作製した。
【０３８０】
〔比較例５６〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較例の電子写真感光体を作製した。
【０３８２】
上記実施例４９から５６および比較例４９から５６で得られた各感光体について前記と同様の方法で感光体特性を測定した。結果を表１６に示す。
【０３８４】
【表１６】
次に電荷輸送材料として一般式（Ｉ）で示される化合物と一般式（IX）で示される化合物を併用した場合について、実施例５７から６４および比較例５７から６４により説明する。
【０３８６】
〔実施例５７〕
外径７０ｍｍのアルミニウムシリンダー上に下記組成の下引層塗工液、電荷発生層塗工液、電荷輸送層塗工液を順次、塗布・乾燥して各々４μｍの下引層、０．２μｍの電荷発生層、２２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０３８７】
〔電荷輸送層塗工液〕
化合物ＮＯ．IX−６の化合物 ３部
化合物ＮＯ．I−２の化合物 ６部
ポリカーボネート（帝人化成社製：パンライトＫ−１３００） １０部
テトラヒドロフラン ７５部
【０３９０】
〔比較例５７〕
実施例５７の電荷輸送層塗工液を下記組成のものに変えた以外は実施例５７と同様にして比較例の電子写真感光体を作製した。
【０３９１】
〔実施例５８〕
アルミニウムシリンダー表面を陽極酸化処理した後、封孔処理を行った。この上に、下記電荷発生層塗工液、電荷輸送層塗工液を順次塗布・乾燥して各々０．２μｍの電荷発生層、２０μｍの電荷輸送層を形成し本発明の電子写真感光体を作製した。
【０３９３】
〔比較例５８〕
実施例５８の電荷輸送層塗工液において、化合物ＮＯ．IX−１３の化合物を添加しないこと以外は実施例５８と同様にして比較例の電子写真感光体を作製した。
【０３９６】
〔実施例５９〕
アルミニウムシリンダー上に下記組成の下引層塗工液、下記組成の電荷発生層塗工液、下記組成の電荷輸送層塗工液を、順次塗布・乾燥して各々２μｍの下引層、０．２μｍの電荷発生層、２μｍの電荷輸送層を形成し、本発明の電子写真感光体を作製した。
【０３９７】
〔電荷発生層塗工液〕
下記構造式（化１３）の電荷発生材料 ３部
【化１３】
シクロヘキサノン １５０部
４−メチル−２−ペンタノン １００部
【０３９９】
〔比較例５９〕
実施例５９の電荷輸送層塗工液を下記組成のものにした以外は実施例５９と同様にして比較例の電子写真感光体を作製した。
【０４０１】
〔実施例６０〕
実施例５７の電荷輸送層塗工液を下記組成のものにした以外は実施例５７と同様にして本発明の電子写真感光体を作製した。
【０４０３】
〔比較例６０〕
実施例６０の電荷輸送層塗工液を下記組成のものにした以外は実施例６０と同様にして比較例の電子写真感光体を作製した。
【０４０５】
〔実施例６１〕
実施例５８の電荷輸送層塗工液を下記組成のものにした以外は実施例５８と同様にして本発明の電子写真感光体を作製した。
【０４０７】
〔電荷輸送層塗工液〕
化合物ＮＯ．IX−２の化合物 ２部
化合物ＮＯ．I−４４の化合物 ７部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０４０８】
〔比較例６１〕
実施例６１の電荷輸送層塗工液を下記組成のものにした以外は実施例６１と同様にして比較例の電子写真感光体を作製した。
【０４０９】
〔電荷輸送層塗工液〕
化合物ＮＯ．IX−２の化合物 ９部
ポリカーボネート（出光石油化学社製：Ａ２７００） １０部
塩化メチレン ８０部
【０４１０】
〔実施例６２〕
実施例５９電荷輸送層塗工液を下記組成のものにした以外は実施例５９と同様にして本発明の電子写真感光体を作製した。
【０４１１】
〔比較例６２〕
実施例６２の電荷輸送層塗工液において、化合物ＮＯ．I−４７の化合物を添加しないこと以外は実施例６２と同様にして比較例の電子写真感光体を作製した。
【０４１３】
〔実施例６３〕
アルミニウムシリンダー上に下記組成の共晶錯体光導電層塗工液を塗布・乾燥し、厚さ２５μｍの共晶錯体光導電層を形成し本発明の電子写真感光体を作製した。
【０４１４】
〔比較例６３〕
実施例６３の電荷輸送層塗工液において、化合物ＮＯ．IX−２１の化合物を添加しないこと以外は実施例６３と同様にして比較例の電子写真感光体を作製した。
【０４１６】
〔実施例６４〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し本発明の電子写真感光体を作製した。
【０４１７】
〔感光層塗工液〕
下記構造式（化１４）の電荷発生材料 ３部
【化１４】
（三菱瓦斯化学社製：ユーピロン Ｓ−２０００） ２１部
化合物ＮＯ．IX−３の化合物 ８部
化合物ＮＯ．I−８６の化合物 １０部
テトラヒドロフラン ２５０部
【０４１８】
〔比較例６４〕
アルミニウムシリンダー上に下記組成の感光層塗工液を塗布・乾燥し、厚さ２３μｍの単層感光層を形成し比較例の電子写真感光体を作製した。
【０４１９】
上記実施例５７から６４および比較例５７から６４で得られた各感光体について上記と同様の方法で感光体特性を測定した。結果を表１７に示す。
【０４２１】
【表１７】
【発明の効果】
以上のように、本発明によれば、感光層に電荷輸送材料して上記特定の２種類の化合物を用いることにより高感度を維持しながら繰り返し使用によっても優れた安定性を有する電子写真感光体が得られる。
【図面の簡単な説明】
【図１】本発明が係る単層感光体の説明図である。
【図２】本発明が係る積層感光体の説明図である。
【図３】本発明が係る積層感光体の説明図である。
【符号の説明】
１１ 導電性支持体
１５ 単層感光層
１７ 電荷発生層
１９ 電荷輸送層[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an electrophotographic photosensitive member, and more particularly to an electrophotographic photosensitive member using a specific charge transport material and excellent in photosensitivity, printing characteristics, and repeated use characteristics.
[0002]
[Prior art]
In an organic electrophotographic photosensitive member, a function-separated type photosensitive member in which a charge generation layer and a charge transport layer are laminated has been noticed and put into practical use in order to increase the sensitivity. The mechanism of electrostatic latent image formation in this function-separated type photoreceptor is that when the photoreceptor is charged and then irradiated with light, the light is absorbed by the charge generation layer, and the charge generation layer that has absorbed the light generates charge carriers. This charge carrier is injected into the charge transport layer, moves in the charge transport layer (or photosensitive layer) according to the electric field generated by charging, and forms an electrostatic latent image by neutralizing the charge on the surface of the photoreceptor. To do.
[0003]
Various photoconductor materials have been developed so far, but in order to make them excellent electrophotographic photoconductors that can be put into practical use, sensitivity, receptive potential, potential holding property, potential stability, residual potential, and spectral characteristics are required. Various characteristics such as representative electrophotographic characteristics, mechanical durability such as abrasion resistance, chemical stability against heat, light, discharge products, and the like are required. In particular, it is important to have high sensitivity and excellent repeated stability. However, as described above, a certain degree of high sensitivity characteristics can be achieved by a combination of an appropriate charge generation material and charge transport material. is there. On the other hand, in addition to this, studies have been made on the combination of mechanical durability, but depending on the combination of conventionally proposed charge generation materials and charge transport materials, a material that satisfies all of the above conditions can be obtained. It was not done. Therefore, there has been a strong demand for the completion of an electrophotographic photosensitive member that maintains high sensitivity and is excellent in stability by repeated use by using conventionally proposed charge generation materials and charge transport materials.
[0004]
[Problems to be solved by the invention]
An object of the present invention is to provide an electrophotographic photosensitive member that exhibits excellent stability even after repeated use without losing high sensitivity.
[0005]
[Means for Solving the Problems]
According to the present invention, the following inventions are provided.
First, in the present invention,Compound represented by general formula (I)One thingCompound represented by general formula (II),oneCompound represented by general formula (III),oneCompound represented by general formula (IV),oneCompound represented by general formula (V),oneCompound represented by general formula (IV),oneCompound represented by general formula (VII),oneA compound represented by formula (VIII):BiichiCompound represented by general formula (IX)Is shown below.
[Chemical 1]
(1) The compound represented by the general formula (I) and the compound represented by the general formula (II)
(2) The compound represented by the general formula (I) and the compound represented by the general formula (III)
(3) The compound represented by the general formula (I) and the compound represented by the general formula (IV)
(4) The compound represented by the general formula (I) and the compound represented by the general formula (V)
(5) The compound represented by the general formula (I) and the compound represented by the general formula (VI)
(6) The compound represented by the general formula (I) and the compound represented by the general formula (VII)
(7) The compound represented by the general formula (I) and the compound represented by the general formula (VIII)
(8) Compound represented by general formula (I) and compound represented by general formula (IX)
(B(1) An electrophotographic film comprising a single-layer photosensitive layer containing at least one selected from the group consisting of compounds represented by the following (1) to (8) on a conductive support: Photoconductor.
(1) The compound represented by the general formula (I) and the compound represented by the general formula (II)
(2) The compound represented by the general formula (I) and the compound represented by the general formula (III)
(3) The compound represented by the general formula (I) and the compound represented by the general formula (IV)
(4) The compound represented by the general formula (I) and the compound represented by the general formula (V)
(5) The compound represented by the general formula (I) and the compound represented by the general formula (VI)
(6) The compound represented by the general formula (I) and the compound represented by the general formula (VII)
(7) The compound represented by the general formula (I) and the compound represented by the general formula (VIII)
(8) A compound represented by the general formula (I) and a compound represented by the general formula (IX).
[0006]
The present invention is described in detail below.
As a result of repeated studies on the above problems, the present inventors have used the above-mentioned specific combination of charge transport materials for the photosensitive layer, so that the occurrence of image quality defects can be suppressed even after repeated use, and excellent electrophotographic characteristics can be combined. The present inventors have found that an electrophotographic photosensitive member can be obtained, and have reached the present invention.
[0007]
The electrophotographic photosensitive member of the present invention will be described with reference to the drawings. FIG. 1 is a sectional view showing a single-layer photosensitive member in the present invention, and a photosensitive layer 15 is provided on a conductive support 11. . 2 and 3 are cross-sectional views showing examples of the structure of the laminated photoconductor according to the present invention, a
In such a single-layer or multilayer photoreceptor, a charge transport material comprising at least one selected from the compounds represented by the general formula (I) and the compounds represented by the general formulas (II) to (IX). Are used in combination.
[0008]
DETAILED DESCRIPTION OF THE INVENTION
Embodiments of the invention will be described below.
The conductive support 11 has a volume resistance of 1.0 × 10TenA material that exhibits conductivity of Ωcm or less, for example, a metal such as aluminum, nickel, chromium, nichrome, copper, silver, gold, platinum, a metal oxide such as tin oxide, indium oxide, or the like by vapor deposition or sputtering. It is possible to use cylindrical plastic or paper coated, or aluminum, aluminum alloy, nickel, stainless steel, etc. and pipes that have been surface treated by cutting, superfinishing, polishing, etc. it can.
[0009]
Next, the photosensitive layer 15 will be described. For convenience of explanation, the case where the
The
[0010]
The charge generation material may be used alone or in combination of two or more. The
[0011]
Suitable binder resins include polyamide, polyurethane, polyester, epoxy resin, polyketone, polycarbonate, silicone resin, acrylic resin, polyvinyl butyral, polyvinyl formal, polyvinyl ketone, polystyrene, and polyacrylamide. The amount of the binder resin used appropriately is suitably 0 to 2 parts by weight with respect to 1 part by weight of the charge generating material.
[0012]
The
[0013]
The
[0014]
As the charge transport material, a mixture of the compound represented by the general formula (I) and at least one selected from the compounds represented by the general formulas (II) to (IX) is used. Specific examples of these compounds are listed in Table 1 and Tables 2 to 9. The mixing ratio of these compounds is such that the compound represented by the general formula (I) and at least one selected from the compounds represented by the general formulas (II) to (IX) each fall within the range of 5:95 to 95: 5. Good results can be obtained. The amount of the charge transport material used is 15 to 75% by weight, preferably 25 to 65% by weight, based on the total constituent material of the charge transport layer in the laminated photoconductor.
[0015]
[Table 1- (1)]
[Table 1- (2)]
[Table 1- (3)]
[Table 1- (4)]
[Table 1- (5)]
[Table 1- (6)]
[Table 1- (7)]
[Table 1- (8)]
[Table 1- (9)]
[Table 2- (1)]
[Table 2- (2)]
[Table 2- (3)]
[Table 2- (4)]
[Table 2- (5)]
[Table 2- (6)]
[Table 2- (7)]
[Table 2- (8)]
[Table 2- (9)]
[Table 3- (1)]
[Table 3- (2)]
[Table 4- (1)]
[Table 4- (2)]
[Table 4- (3)]
[Table 4- (4)]
[Table 4- (5)]
[Table 4- (6)]
[Table 4- (7)]
[Table 4- (8)]
[Table 4- (9)]
[Table 4- (10)]
[Table 4- (11)]
[Table 4- (12)]
[Table 4- (13)]
[Table 4- (14)]
[Table 4- (15)]
[Table 4- (16)]
[Table 4- (17)]
[Table 4- (18)]
[Table 5- (1)]
[Table 5- (2)]
[Table 5- (3)]
[Table 5- (4)]
[Table 5- (5)]
[Table 5- (6)]
[Table 5- (7)]
[Table 5- (8)]
[Table 5- (9)]
[Table 5- (10)]
[Table 5- (11)]
[Table 5- (12)]
[Table 5- (13)]
[Table 5- (14)]
[Table 5- (15)]
[Table 5- (16)]
[Table 5- (17)]
[Table 5- (18)]
[Table 5- (19)]
[Table 5- (20)]
[Table 5- (21)]
[Table 5- (22)]
[Table 5- (23)]
[Table 5- (24)]
[Table 5- (25)]
[Table 5- (26)]
[Table 5- (27)]
[Table 5- (28)]
[Table 5- (29)]
[Table 5- (30)]
[Table 5- (31)]
[Table 5- (32)]
[Table 5- (33)]
[Table 5- (34)]
[Table 5- (35)]
[Table 5- (36)]
[Table 5- (37)]
[Table 5- (38)]
[Table 5- (39)]
[Table 5- (40)]
[Table 5- (41)]
[Table 5- (42)]
[Table 5- (43)]
[Table 6- (1)]
[Table 6- (2)]
[Table 6- (3)]
[Table 6- (4)]
[Table 7- (1)]
[Table 7- (2)]
[Table 8- (1)]
[Table 8- (2)]
[Table 8- (3)]
[Table 8- (4)]
[Table 9- (1)]
[Table 9- (2)]
[Table 9- (3)]
[Table 9- (4)]
In addition to a charge transporting material comprising a compound represented by the general formula (I) and at least one selected from the compounds represented by the general formulas (II) to (IX), a known electron transporting charge may be used. A transport material and / or a hole transport charge transport material may be used in combination.
[0111]
Examples of the binder resin used in the
[0112]
As the solvent, tetrahydrofuran, dioxane, toluene, 2-butanone, monochlorobenzene, dichloroethane, methylene chloride and the like are used.
[0113]
The thickness of the
[0114]
In the present invention, a plasticizer or a leveling agent may be added to the
[0115]
Next, the case where the photosensitive layer 15 has a single layer structure will be described. Many of the materials used in this case are the same as those used in the functional separation type composed of the charge generation material and the charge transport material.
[0116]
That is, at least a charge generating material and a charge transport material consisting of at least one compound selected from the compounds represented by the general formulas (I) and (II) to (IX), together with the binder resin, are suitable. It can be formed by dissolving or dispersing in an appropriate solvent, coating and drying. Further, if necessary, a plasticizer, a ladle agent and the like can be added.
As the binder resin, the binder resin previously mentioned in the
[0117]
The eutectic complex formed from a pyrylium dye and a bisphenol A polycarbonate comprises a compound represented by general formula (I) and at least one selected from compounds represented by general formulas (II) to (IX). A photosensitive layer to which a charge transport material is added can also be used as a single-layer photosensitive layer.
[0118]
Further, charge generation is carried out mainly comprising a charge transporting material comprising at least one compound selected from the compounds represented by general formula (I) and the compounds represented by general formulas (II) to (IX) and a binder resin. A single-layer photosensitive layer containing no material as an active ingredient is also useful as a photoreceptor having sensitivity to blue light to ultraviolet light.
[0119]
The mixing ratio of the two specific types of charge transport materials in the single-layer photosensitive layer is preferably in the range of 5:95 to 95: 5, as in the case of the laminated photosensitive layer, and the amount used is the total constitution of the single-layer photosensitive layer It is 5 to 75% by weight, preferably 10 to 65% by weight, based on the material. The film thickness of the single-layer photosensitive layer is suitably 5 to 100 μm.
[0120]
In the electrophotographic photoreceptor of the present invention, an undercoat layer can be provided between the conductive support 11 and the photosensitive layer. In general, the undercoat layer is mainly composed of a resin. However, considering that the photosensitive layer is applied with a solvent on these resins, the resin may be a resin having a high resistance to a general organic solvent. desirable. Examples of such resins include water-soluble resins such as polyvinyl alcohol, casein, and sodium polyacrylate, alcohol-soluble resins such as copolymer nylon and methoxymethylated nylon, polyurethane, melamine resins, alkyd-melamine resins, and epoxy resins. Examples thereof include curable resins that form a three-dimensional network structure.
[0121]
Further, fine powders of metal oxides exemplified by titanium oxide, silica, alumina, zirconium oxide, tin oxide, indium oxide and the like may be added to the undercoat layer in order to prevent moire and reduce residual potential. These undercoat layers can be formed using an appropriate solvent and coating method as in the photosensitive layer described above.
[0122]
Furthermore, a metal oxide layer formed by, for example, a sol-gel method using a silane coupling agent, a titanium coupling agent, a chromium coupling agent, or the like is also useful as the undercoat layer of the present invention.
[0123]
In addition to this, the undercoat layer of the present invention includes Al.2OThreePrepared by anodic oxidation, organic matter such as polyparaxylylene (parylene), SiO, SnO2TiO2, ITO, CeO2A material provided with an inorganic material such as a vacuum thin film can also be used favorably. The thickness of the undercoat layer is suitably from 0 to 5 μm.
[0124]
In the electrophotographic photoreceptor of the present invention, a protective layer may be provided on the photosensitive layer for the purpose of protecting the photosensitive layer. Materials used for this include ABS resin, ACS resin, olefin-vinyl monomer copolymer, chlorinated polyether, allyl resin, phenol resin, polyacetal, polyamide, polyamideimide, polyacrylate, polyallylsulfone, polybutylene, Polybutylene terephthalate, polycarbonate, polyethersulfone, polyethylene, polyethylene terephthalate, polyimide, acrylic resin, polymethylpentene, polypropylene, polyphenylene oxide, polysulfone, AS resin, AB resin, BS resin, polyurethane, polyvinyl chloride, polyvinylidene chloride, Resins such as epoxy resins can be used.
[0125]
In addition to the protective layer, for the purpose of improving wear resistance, fluorine resin such as polytetrafluoroethylene, silicone resin, and those in which inorganic materials such as titanium oxide, tin oxide and potassium titanate are dispersed in these resins, etc. Can be added.
As a method for forming the protective layer, a normal coating method is employed. In addition, about 0.5-10 micrometers is suitable for the thickness of a protective layer. In addition to the above, known materials such as i-C and a-SiC formed by a vacuum thin film manufacturing method can also be used as the protective layer.
[0126]
In the present invention, another intermediate layer can be provided between the photosensitive layer and the protective layer. In the intermediate layer, a binder resin is generally used as a main component. Examples of these resins include polyamide, alcohol-soluble nylon, water-soluble polyvinyl butyral, polyvinyl butyral, and polyvinyl alcohol.
As a method for forming the intermediate layer, a normal coating method is employed as described above. In addition, about 0.05-2 micrometers is suitable for the thickness of an intermediate | middle layer.
[0127]
【Example】
The following examples illustrate the present invention in detail, and the present invention is not limited by the examples. In addition, all the parts in an Example are a weight part.
First, Examples 1 to 8 and Comparative Examples 1 to 8 illustrate cases where the compounds represented by formulas (I) and (II) are used in combination as charge transport materials.
[0128]
[Example 1]
An undercoating layer coating solution, a charge generation layer coating solution, and a charge transporting layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to form an undercoating layer of 4 μm and 0.2 μm, respectively. The electrophotographic photosensitive member of the present invention was prepared by forming a charge generation layer of 22 μm and a charge transport layer of 22 μm.
[0129]
[Charge transport layer coating solution]
Compound NO. II-1 Compound 3 parts
Compound NO. Compound of I-2 6 parts
10 parts of polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300)
75 parts of tetrahydrofuran
[0132]
[Comparative Example 1]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 1 except that the charge transport layer coating solution of Example 1 was changed to one having the following composition.
[0133]
[Example 2]
After anodizing the surface of the aluminum cylinder, sealing treatment was performed. On top of this, the following charge generation layer coating solution and charge transport layer coating solution are sequentially applied and dried to form a 0.2 μm charge generation layer and a 20 μm charge transport layer, respectively. Produced.
[0135]
[Comparative Example 2]
In the charge transport layer coating solution of Example 2, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 2 except that the compound II-6 was not added.
[0138]
Example 3
On an aluminum cylinder, an undercoat layer coating solution having the following composition, a charge generation layer coating solution having the following composition, and a charge transport layer coating solution having the following composition are sequentially applied and dried to form an undercoat layer of 2 μm each. A 2 μm charge generation layer and a 2 μm charge transport layer were formed to produce the electrophotographic photoreceptor of the present invention.
[0139]
[Charge generation layer coating solution]
3 parts of charge generation material of the following structural formula (Formula 13)
Embedded image
150 parts of cyclohexanone
4-methyl-2-pentanone 100 parts
[0141]
[Comparative Example 3]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 3 except that the charge transport layer coating solution of Example 3 had the following composition.
[0143]
Example 4
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 1 except that the charge transport layer coating solution of Example 1 had the following composition.
[0145]
[Comparative Example 4]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 4 except that the charge transport layer coating solution of Example 4 had the following composition.
[0147]
Example 5
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 2 except that the charge transport layer coating solution of Example 2 had the following composition.
[0149]
[Charge transport layer coating solution]
Compound NO. II-35 Compound 2 parts
Compound NO. I-44 Compound 7 parts
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0150]
[Comparative Example 5]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 5 except that the charge transport layer coating solution of Example 5 had the following composition.
[0151]
[Charge transport layer coating solution]
Compound NO. Compound II-35 9 parts
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0152]
Example 6
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 3 except that the charge transport layer coating solution of Example 3 had the following composition.
[0153]
[Comparative Example 6]
In the charge transport layer coating solution of Example 6, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 6 except that the compound I-47 was not added.
[0155]
Example 7
An eutectic complex photoconductive layer coating solution having the following composition was applied on an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm, thereby producing an electrophotographic photoreceptor of the present invention.
[0156]
[Comparative Example 7]
In the charge transport layer coating solution of Example 7, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 7 except that the compound of II-48 was not added.
[0158]
Example 8
On the aluminum cylinder, a photosensitive layer coating solution having the following composition was applied and dried to form a single-layer photosensitive layer having a thickness of 23 μm to produce the electrophotographic photosensitive member of the present invention.
[0159]
[Comparative Example 8]
A photosensitive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby preparing a comparative electrophotographic photosensitive member.
[0161]
The following measurements were carried out on the photoreceptors of the above examples and comparative examples using an evaluation apparatus disclosed in Japanese Patent Application Laid-Open No. 60-1000016. Potential Vm (V) after 20 seconds of charging with corona discharge voltage -6.0 kV (or +5.6 kV), potential Vo (V) after 20 seconds of dark decay, residual potential after 20 seconds of exposure with white light with intensity 6 lux The exposure amount E1 / 2 [lux · sec] required to attenuate VR (V) and further the potential Vo to 1/2 was measured. The potential holding ratio is defined as Vo / Vm.
Further, each photoconductor was mounted on a Ricoh copier FT-3300 (or the photoconductor was modified so that it could be positively charged), and 30,000 continuous copies were made, and the presence or absence of an abnormal image was visually determined. Each photoconductor after the copying test was measured for the photoconductor characteristics by the same method as described above. The test results are shown in Table 10.
[0163]
[Table 10]
Next, the case where the compound represented by the general formula (I) and the compound represented by the general formula (III) are used in combination as the charge transport material will be described with reference to Examples 9 to 16 and Comparative Examples 9 to 16.
[0165]
Example 9
An undercoating layer coating solution, a charge generation layer coating solution, and a charge transporting layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to form an undercoating layer of 4 μm and 0.2 μm, respectively. The electrophotographic photosensitive member of the present invention was prepared by forming a charge generation layer of 22 μm and a charge transport layer of 22 μm.
[0166]
[Charge transport layer coating solution]
Compound NO. III-8 compounds 3 parts
Compound NO. Compound of I-2 6 parts
10 parts of polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300)
75 parts of tetrahydrofuran
[0169]
[Comparative Example 9]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 9 except that the charge transport layer coating solution in Example 9 was changed to the one having the following composition.
[0170]
Example 10
After anodizing the surface of the aluminum cylinder, sealing treatment was performed. On top of this, the following charge generation layer coating solution and charge transport layer coating solution are sequentially applied and dried to form a 0.2 μm charge generation layer and a 20 μm charge transport layer, respectively. Produced.
[0172]
[Comparative Example 10]
In the charge transport layer coating solution of Example 10, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 10 except that the compound of III-10 was not added.
[0175]
Example 11
On an aluminum cylinder, an undercoat layer coating solution having the following composition, a charge generation layer coating solution having the following composition, and a charge transport layer coating solution having the following composition are sequentially applied and dried to form an undercoat layer of 2 μm each. A 2 μm charge generation layer and a 2 μm charge transport layer were formed to produce the electrophotographic photoreceptor of the present invention.
[0176]
[Charge generation layer coating solution]
3 parts of charge generation material of the following structural formula (Formula 13)
Embedded image
150 parts of cyclohexanone
4-methyl-2-pentanone 100 parts
[0178]
[Comparative Example 11]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 11 except that the charge transport layer coating solution of Example 11 had the following composition.
[0180]
Example 12
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 9 except that the charge transport layer coating solution of Example 9 had the following composition.
[0182]
[Comparative Example 12]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 12 except that the charge transport layer coating solution of Example 12 had the following composition.
[0184]
Example 13
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 10 except that the charge transport layer coating solution of Example 10 had the following composition.
[0186]
[Charge transport layer coating solution]
Compound NO. Compound III-17 2 parts
Compound NO. I-44 Compound 7 parts
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0187]
[Comparative Example 13]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 13 except that the charge transport layer coating solution of Example 13 had the following composition.
[0188]
[Charge transport layer coating solution]
Compound NO. 9 parts of compound III-17
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0189]
Example 14
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 11 except that the charge transport layer coating solution of Example 11 had the following composition.
[0190]
[Comparative Example 14]
In the charge transport layer coating solution of Example 14, the compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 14 except that the compound I-47 was not added.
[0192]
Example 15
An eutectic complex photoconductive layer coating solution having the following composition was applied on an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm, thereby producing an electrophotographic photoreceptor of the present invention.
[0193]
[Comparative Example 15]
In the charge transport layer coating solution of Example 15, the compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 15 except that the compound III-20 was not added.
[0195]
Example 16
On the aluminum cylinder, a photosensitive layer coating solution having the following composition was applied and dried to form a single-layer photosensitive layer having a thickness of 23 μm to produce the electrophotographic photosensitive member of the present invention.
[0196]
[Comparative Example 16]
A photosensitive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby preparing a comparative electrophotographic photosensitive member.
[0198]
For each of the photoreceptors obtained in Examples 9 to 16 and Comparative Examples 9 to 16, the photoreceptor characteristics were measured by the same method as described above. The results are shown in Table 11.
[0200]
[Table 11]
Next, Examples 17 to 24 and Comparative Examples 17 to 24 illustrate the case where the compound represented by the general formula (I) and the compound represented by the general formula (IV) are used in combination as a charge transport material.
[0202]
Example 17
An undercoating layer coating solution, a charge generation layer coating solution, and a charge transporting layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to form an undercoating layer of 4 μm and 0.2 μm, respectively. The electrophotographic photosensitive member of the present invention was prepared by forming a charge generation layer of 22 μm and a charge transport layer of 22 μm.
[0203]
[Charge transport layer coating solution]
Compound NO. Compound IV-2 3 parts
Compound NO. Compound of I-2 6 parts
10 parts of polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300)
75 parts of tetrahydrofuran
[0206]
[Comparative Example 17]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 17 except that the charge transport layer coating solution of Example 17 was changed to the following composition.
[0207]
Example 18
After anodizing the surface of the aluminum cylinder, sealing treatment was performed. On top of this, the following charge generation layer coating solution and charge transport layer coating solution are sequentially applied and dried to form a 0.2 μm charge generation layer and a 20 μm charge transport layer, respectively. Produced.
[0209]
[Comparative Example 18]
In the charge transport layer coating solution of Example 18, the compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 18 except that the compound IV-14 was not added.
[0212]
Example 19
On an aluminum cylinder, an undercoat layer coating solution having the following composition, a charge generation layer coating solution having the following composition, and a charge transport layer coating solution having the following composition are sequentially applied and dried to form an undercoat layer of 2 μm each. A 2 μm charge generation layer and a 2 μm charge transport layer were formed to produce the electrophotographic photoreceptor of the present invention.
[0213]
[Charge generation layer coating solution]
3 parts of charge generation material of the following structural formula (Formula 13)
Embedded image
150 parts of cyclohexanone
4-methyl-2-pentanone 100 parts
[0215]
[Comparative Example 19]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 19 except that the charge transport layer coating solution of Example 19 had the following composition.
[0217]
Example 20
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 17 except that the charge transport layer coating solution of Example 17 had the following composition.
[0219]
[Comparative Example 20]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 20 except that the charge transport layer coating solution of Example 20 had the following composition.
[0221]
Example 21
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 18 except that the charge transport layer coating solution of Example 18 had the following composition.
[0223]
[Charge transport layer coating solution]
Compound NO. Compound IV-51 2 parts
Compound NO. Compound 7 of I-44
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0224]
[Comparative Example 21]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 21 except that the charge transport layer coating solution of Example 21 had the following composition.
[0225]
[Charge transport layer coating solution]
Compound NO. Compound IV-51 9 parts
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0226]
[Example 22]
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 19 except that the charge transport layer coating solution of Example 19 had the following composition.
[0227]
[Comparative Example 22]
In the charge transport layer coating solution of Example 22, the compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 22 except that the compound I-47 was not added.
[0229]
Example 23
An eutectic complex photoconductive layer coating solution having the following composition was applied on an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm, thereby producing an electrophotographic photoreceptor of the present invention.
[0230]
[Comparative Example 23]
In the charge transport layer coating solution of Example 23, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 23 except that the compound of IV-98 was not added.
[0232]
Example 24
On the aluminum cylinder, a photosensitive layer coating solution having the following composition was applied and dried to form a single-layer photosensitive layer having a thickness of 23 μm to produce the electrophotographic photosensitive member of the present invention.
[0233]
[Comparative Example 24]
A photosensitive layer coating solution having the following composition was coated on an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby preparing a comparative electrophotographic photosensitive member.
[0235]
The photoreceptor characteristics of the photoreceptors obtained in Examples 17 to 24 and Comparative Examples 17 to 24 were measured in the same manner as described above. The results are shown in Table 12.
[0237]
[Table 12]
Next, the case where the compound represented by the general formula (I) and the compound represented by the general formula (V) are used in combination as the charge transport material will be described with reference to Examples 25 to 32 and Comparative Examples 25 to 32.
[0239]
Example 25
An undercoat layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to form a 4 μm undercoat layer and a 0.2 μm undercoat layer, respectively. A charge generation layer and a 22 μm charge transport layer were formed to produce an electrophotographic photoreceptor of the present invention.
[0240]
[Charge transport layer coating solution]
Compound NO. V-9 compound 3 parts
Compound NO. Compound of I-2 6 parts
10 parts of polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300)
75 parts of tetrahydrofuran
[0243]
[Comparative Example 25]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 25 except that the charge transport layer coating solution of Example 25 was changed to the following composition.
[0244]
Example 26
After anodizing the surface of the aluminum cylinder, sealing treatment was performed. On top of this, the following charge generation layer coating solution and charge transport layer coating solution are sequentially applied and dried to form a 0.2 μm charge generation layer and a 20 μm charge transport layer, respectively. Produced.
[0246]
[Comparative Example 26]
In the charge transport layer coating solution of Example 26, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 26 except that the V-19 compound was not added.
[0249]
Example 27
An undercoat layer coating solution having the following composition, a charge generation layer coating solution having the following composition, and a charge transport layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder, and each 2. A 2 μm charge generation layer and a 2 μm charge transport layer were formed to produce the electrophotographic photoreceptor of the present invention.
[0250]
[Charge generation layer coating solution]
3 parts of charge generation material of the following structural formula (Formula 13)
Embedded image
150 parts of cyclohexanone
4-methyl-2-pentanone 100 parts
[0252]
[Comparative Example 27]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 27 except that the charge transport layer coating solution of Example 27 had the following composition.
[0254]
Example 28
An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 25 except that the charge transport layer coating solution of Example 25 had the following composition.
[0256]
[Comparative Example 28]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 28 except that the charge transport layer coating solution of Example 28 had the following composition.
[0258]
Example 29
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 26 except that the charge transport layer coating solution of Example 26 had the following composition.
[0260]
[Charge transport layer coating solution]
Compound NO. 2 parts of V-81 compound
Compound NO. Compound 7 of I-44
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0261]
[Comparative Example 29]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 29 except that the charge transport layer coating solution of Example 29 had the following composition.
[0262]
[Charge transport layer coating solution]
Compound NO. 9 parts of V-81 compound
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0263]
Example 30
An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 27 except that the charge transport layer coating solution of Example 27 had the following composition.
[Comparative Example 30]
In the charge transport layer coating solution of Example 30, the compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 30 except that the compound I-47 was not added.
[0265]
Example 31
An eutectic complex photoconductive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm, thereby producing the electrophotographic photoreceptor of the present invention.
[0266]
[Comparative Example 31]
In the charge transport layer coating solution of Example 31, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 31 except that the V-116 compound was not added.
[0268]
[Example 32]
A photosensitive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby producing the electrophotographic photosensitive member of the present invention.
[0269]
[Comparative Example 32]
A photosensitive layer coating solution having the following composition was coated on an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby preparing a comparative electrophotographic photosensitive member.
[0271]
The photoreceptor characteristics of the photoreceptors obtained in Examples 25 to 32 and Comparative Examples 25 to 32 were measured in the same manner as described above. The results are shown in Table 13.
[0273]
[Table 13]
Next, Examples 33 to 40 and Comparative Examples 33 to 40 illustrate the case where the compound represented by the general formula (I) and the compound represented by the general formula (VI) are used in combination as a charge transport material.
[0275]
Example 33
An undercoat layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to form a 4 μm undercoat layer and a 0.2 μm undercoat layer, respectively. A charge generation layer and a 22 μm charge transport layer were formed to produce an electrophotographic photoreceptor of the present invention.
[0276]
[Charge transport layer coating solution]
Compound NO. Compound of VI-3 3 parts
Compound NO. Compound of I-2 6 parts
10 parts of polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300)
75 parts of tetrahydrofuran
[0279]
[Comparative Example 33]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 33 except that the charge transport layer coating solution in Example 33 was changed to the one having the following composition.
[0280]
Example 34
After anodizing the surface of the aluminum cylinder, sealing treatment was performed. On top of this, the following charge generation layer coating solution and charge transport layer coating solution are sequentially applied and dried to form a 0.2 μm charge generation layer and a 20 μm charge transport layer, respectively. Produced.
[0282]
[Comparative Example 34]
In the charge transport layer coating solution of Example 34, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 34 except that the compound VI-6 was not added.
[0285]
Example 35
An undercoat layer coating solution having the following composition, a charge generation layer coating solution having the following composition, and a charge transport layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder, and each 2. A 2 μm charge generation layer and a 2 μm charge transport layer were formed to produce the electrophotographic photoreceptor of the present invention.
[0286]
[Charge generation layer coating solution]
3 parts of charge generation material of the following structural formula (Formula 13)
Embedded image
150 parts of cyclohexanone
4-methyl-2-pentanone 100 parts
[0288]
[Comparative Example 35]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 35 except that the charge transport layer coating solution of Example 35 had the following composition.
[0290]
Example 36
An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 33 except that the charge transport layer coating solution of Example 33 had the following composition.
[0292]
[Comparative Example 36]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 36 except that the charge transport layer coating solution of Example 36 had the following composition.
[0294]
Example 37
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 34 except that the charge transport layer coating solution of Example 34 had the following composition.
[0296]
[Charge transport layer coating solution]
Compound NO. Compound VI-13 2 parts
Compound NO. Compound 7 of I-44
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0297]
[Comparative Example 37]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 37 except that the charge transport layer coating solution of Example 37 had the following composition.
[0298]
[Charge transport layer coating solution]
Compound NO. 9 parts of the compound of VI-13
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0299]
Example 38
An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 35 except that the charge transport layer coating solution of Example 35 had the following composition.
[0300]
[Comparative Example 38]
In the charge transport layer coating solution of Example 38, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 38 except that the compound I-47 was not added.
[0302]
Example 39
An eutectic complex photoconductive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm, thereby producing the electrophotographic photoreceptor of the present invention.
[0303]
[Comparative Example 39]
In the charge transport layer coating solution of Example 39, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 39 except that the compound VI-9 was not added.
[0305]
Example 40
A photosensitive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby producing the electrophotographic photosensitive member of the present invention.
[0306]
[Photosensitive layer coating solution] 3 parts of charge generating material of the following structural formula (Formula 14)
Embedded image
[Comparative Example 40]
A photosensitive layer coating solution having the following composition was coated on an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby preparing a comparative electrophotographic photosensitive member.
[0308]
The photoreceptor characteristics of the photoreceptors obtained in Examples 33 to 40 and Comparative Examples 33 to 40 were measured in the same manner as described above. The results are shown in Table 14.
[0310]
[Table 14]
Next, the case where the compound represented by the general formula (I) and the compound represented by the general formula (VII) are used in combination as the charge transport material will be described with reference to Examples 41 to 48 and Comparative Examples 41 to 48.
[0312]
Example 41
An undercoat layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to form a 4 μm undercoat layer and a 0.2 μm undercoat layer, respectively. A charge generation layer and a 22 μm charge transport layer were formed to produce an electrophotographic photoreceptor of the present invention.
[0313]
[Charge transport layer coating solution]
Compound NO. Compound VII-1 3 parts
Compound NO. Compound of I-2 6 parts
10 parts of polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300)
75 parts of tetrahydrofuran
[0316]
[Comparative Example 41]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 41 except that the charge transport layer coating solution of Example 41 was changed to the one having the following composition.
[0317]
Example 42
After anodizing the surface of the aluminum cylinder, sealing treatment was performed. On top of this, the following charge generation layer coating solution and charge transport layer coating solution are sequentially applied and dried to form a 0.2 μm charge generation layer and a 20 μm charge transport layer, respectively. Produced.
[0319]
[Comparative Example 42]
In the charge transport layer coating solution of Example 42, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 42 except that the compound of VII-3 was not added.
[0322]
Example 43
An undercoat layer coating solution having the following composition, a charge generation layer coating solution having the following composition, and a charge transport layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder, and each 2. A 2 μm charge generation layer and a 2 μm charge transport layer were formed to produce the electrophotographic photoreceptor of the present invention.
[0323]
[Charge generation layer coating solution]
3 parts of charge generation material of the following structural formula (Formula 13)
Embedded image
150 parts of cyclohexanone
4-methyl-2-pentanone 100 parts
[0325]
[Comparative Example 43]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 43 except that the charge transport layer coating solution of Example 43 had the following composition.
[0327]
Example 44
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 41 except that the charge transport layer coating solution of Example 41 had the following composition.
[0329]
[Comparative Example 44]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 44 except that the charge transport layer coating solution of Example 44 had the following composition.
[0331]
Example 45
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 42 except that the charge transport layer coating solution of Example 42 had the following composition.
[0333]
[Charge transport layer coating solution]
Compound NO. Compound VII-11 2 parts
Compound NO. Compound 7 of I-44
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0334]
[Comparative Example 45]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 45 except that the charge transport layer coating solution of Example 45 had the following composition.
[0335]
[Charge transport layer coating solution]
Compound NO. 9 parts of the compound of VII-11
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0336]
Example 46
An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 43 except that the charge transport layer coating solution of Example 43 had the following composition.
[0337]
[Comparative Example 46]
In the charge transport layer coating solution of Example 46, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 46 except that the compound I-47 was not added.
[0339]
Example 47
An eutectic complex photoconductive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm, thereby producing the electrophotographic photoreceptor of the present invention.
[0340]
[Comparative Example 47]
In the charge transport layer coating solution of Example 47, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 47 except that the compound of VII-2 was not added.
[0342]
Example 48
A photosensitive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby producing the electrophotographic photosensitive member of the present invention.
[0343]
[Comparative Example 48]
A photosensitive layer coating solution having the following composition was coated on an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby preparing a comparative electrophotographic photosensitive member.
[0345]
The photoreceptor characteristics of the photoreceptors obtained in Examples 41 to 48 and Comparative Examples 41 to 48 were measured in the same manner as described above. The results are shown in Table 15.
[0347]
[Table 15]
Next, the case where the compound represented by the general formula (I) and the compound represented by the general formula (VIII) are used in combination as the charge transport material will be described with reference to Examples 49 to 56 and Comparative Examples 49 to 56.
[0349]
Example 49
An undercoat layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to form a 4 μm undercoat layer and a 0.2 μm undercoat layer, respectively. A charge generation layer and a 22 μm charge transport layer were formed to produce an electrophotographic photoreceptor of the present invention.
[0350]
[Charge transport layer coating solution]
Compound NO. VIII-11 compound 3 parts
Compound NO. Compound of I-2 6 parts
10 parts of polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300)
75 parts of tetrahydrofuran
[0353]
[Comparative Example 49]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 49 except that the charge transport layer coating solution of Example 49 was changed to one having the following composition.
[0354]
Example 50
After anodizing the surface of the aluminum cylinder, sealing treatment was performed. On top of this, the following charge generation layer coating solution and charge transport layer coating solution are sequentially applied and dried to form a 0.2 μm charge generation layer and a 20 μm charge transport layer, respectively. Produced.
[0356]
[Comparative Example 50]
In the charge transport layer coating solution of Example 50, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 50 except that the compound of VIII-16 was not added.
[0359]
Example 51
An undercoat layer coating solution having the following composition, a charge generation layer coating solution having the following composition, and a charge transport layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder, and each 2. A 2 μm charge generation layer and a 2 μm charge transport layer were formed to produce the electrophotographic photoreceptor of the present invention.
[0360]
[Charge generation layer coating solution]
3 parts of charge generation material of the following structural formula (Formula 13)
Embedded image
150 parts of cyclohexanone
4-methyl-2-pentanone 100 parts
[0362]
[Comparative Example 51]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 51 except that the charge transport layer coating solution of Example 51 had the following composition.
[0364]
Example 52
An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 49 except that the charge transport layer coating solution of Example 49 had the following composition.
[0366]
[Comparative Example 52]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 52 except that the charge transport layer coating solution of Example 52 had the following composition.
[0368]
Example 53
An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 50 except that the charge transport layer coating solution of Example 50 had the following composition.
[0370]
[Charge transport layer coating solution]
Compound NO. Compound VIII-14 2 parts
Compound NO. Compound 7 of I-44
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0371]
[Comparative Example 53]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 53 except that the charge transport layer coating solution of Example 53 had the following composition.
[0372]
[Charge transport layer coating solution]
Compound NO. 9 parts of the compound of VIII-14
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0373]
Example 54
An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 51 except that the charge transport layer coating solution of Example 51 had the following composition.
[0374]
[Comparative Example 54]
In the charge transport layer coating solution of Example 54, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 54 except that the compound I-47 was not added.
[0376]
Example 55
An eutectic complex photoconductive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm, thereby producing the electrophotographic photoreceptor of the present invention.
[0377]
[Comparative Example 55]
In the charge transport layer coating solution of Example 55, Compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 55 except that the compound of VIII-46 was not added.
[0379]
Example 56
A photosensitive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby producing the electrophotographic photosensitive member of the present invention.
[0380]
[Comparative Example 56]
A photosensitive layer coating solution having the following composition was coated on an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby preparing a comparative electrophotographic photosensitive member.
[0382]
The photoreceptor characteristics of the photoreceptors obtained in Examples 49 to 56 and Comparative Examples 49 to 56 were measured in the same manner as described above. The results are shown in Table 16.
[0384]
[Table 16]
Next, the case where the compound represented by the general formula (I) and the compound represented by the general formula (IX) are used in combination as the charge transport material will be described with reference to Examples 57 to 64 and Comparative Examples 57 to 64.
[0386]
Example 57
An undercoat layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder having an outer diameter of 70 mm to form a 4 μm undercoat layer and a 0.2 μm undercoat layer, respectively. A charge generation layer and a 22 μm charge transport layer were formed to produce an electrophotographic photoreceptor of the present invention.
[0387]
[Charge transport layer coating solution]
Compound NO. IX-6 compound 3 parts
Compound NO. Compound of I-2 6 parts
10 parts of polycarbonate (manufactured by Teijin Chemicals Ltd .: Panlite K-1300)
75 parts of tetrahydrofuran
[0390]
[Comparative Example 57]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 57 except that the charge transport layer coating solution of Example 57 was changed to the one having the following composition.
[0390]
Example 58
After anodizing the surface of the aluminum cylinder, sealing treatment was performed. On top of this, the following charge generation layer coating solution and charge transport layer coating solution are sequentially applied and dried to form a 0.2 μm charge generation layer and a 20 μm charge transport layer, respectively. Produced.
[0393]
[Comparative Example 58]
In the charge transport layer coating solution of Example 58, Compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 58 except that the compound of IX-13 was not added.
[0396]
Example 59
An undercoat layer coating solution having the following composition, a charge generation layer coating solution having the following composition, and a charge transport layer coating solution having the following composition are sequentially applied and dried on an aluminum cylinder, and each 2. A 2 μm charge generation layer and a 2 μm charge transport layer were formed to produce the electrophotographic photoreceptor of the present invention.
[0397]
[Charge generation layer coating solution]
3 parts of charge generation material of the following structural formula (Formula 13)
Embedded image
150 parts of cyclohexanone
4-methyl-2-pentanone 100 parts
[0399]
[Comparative Example 59]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 59 except that the charge transport layer coating solution of Example 59 had the following composition.
[0401]
Example 60
An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 57 except that the charge transport layer coating solution of Example 57 had the following composition.
[0403]
[Comparative Example 60]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 60 except that the charge transport layer coating solution of Example 60 had the following composition.
[0405]
Example 61
An electrophotographic photosensitive member of the present invention was produced in the same manner as in Example 58 except that the charge transport layer coating solution of Example 58 had the following composition.
[0407]
[Charge transport layer coating solution]
Compound NO. Compound IX-2 2 parts
Compound NO. Compound 7 of I-44
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0408]
[Comparative Example 61]
A comparative electrophotographic photosensitive member was produced in the same manner as in Example 61 except that the charge transport layer coating solution of Example 61 had the following composition.
[0409]
[Charge transport layer coating solution]
Compound NO. 9 parts of the compound of IX-2
10 parts of polycarbonate (made by Idemitsu Petrochemical Co., Ltd .: A2700)
80 parts of methylene chloride
[0410]
Example 62
Example 59 An electrophotographic photoreceptor of the present invention was produced in the same manner as in Example 59 except that the charge transport layer coating solution had the following composition.
[0411]
[Comparative Example 62]
In the charge transport layer coating solution of Example 62, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 62 except that the compound I-47 was not added.
[0413]
Example 63
An eutectic complex photoconductive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a eutectic complex photoconductive layer having a thickness of 25 μm, thereby producing the electrophotographic photoreceptor of the present invention.
[0414]
[Comparative Example 63]
In the charge transport layer coating solution of Example 63, compound NO. A comparative electrophotographic photosensitive member was produced in the same manner as in Example 63 except that the compound of IX-21 was not added.
[0416]
[Example 64]
A photosensitive layer coating solution having the following composition was applied onto an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby producing the electrophotographic photosensitive member of the present invention.
[0417]
[Photosensitive layer coating solution]
3 parts of charge generation material of the following structural formula (Formula 14)
Embedded image
(Mitsubishi Gas Chemical Co., Ltd .: Iupilon S-2000) 21 parts
Compound NO. Compound IX-3 8 parts
Compound NO. 10 parts of compound I-86
250 parts of tetrahydrofuran
[0418]
[Comparative Example 64]
A photosensitive layer coating solution having the following composition was coated on an aluminum cylinder and dried to form a single-layer photosensitive layer having a thickness of 23 μm, thereby preparing a comparative electrophotographic photosensitive member.
[0419]
The photoreceptor characteristics of the photoreceptors obtained in Examples 57 to 64 and Comparative Examples 57 to 64 were measured in the same manner as described above. The results are shown in Table 17.
[0421]
[Table 17]
【The invention's effect】
As described above, according to the present invention, an electrophotographic photosensitive member having excellent stability even after repeated use while maintaining high sensitivity by using the above-mentioned two kinds of specific compounds as a charge transport material for the photosensitive layer. Is obtained.
[Brief description of the drawings]
FIG. 1 is an explanatory diagram of a single-layer photoconductor according to the present invention.
FIG. 2 is an explanatory diagram of a laminated photoreceptor according to the present invention.
FIG. 3 is an explanatory diagram of a laminated photoconductor according to the present invention.
[Explanation of symbols]
11 Conductive support
15 Single photosensitive layer
17 Charge generation layer
19 Charge transport layer
Claims (2)
（１）一般式（Ｉ）で示される化合物と一般式（ＩＩ）で示される化合物
（２）一般式（Ｉ）で示される化合物と一般式（ＩＩＩ）で示される化合物
（３）一般式（Ｉ）で示される化合物と一般式（ＩＶ）で示される化合物
（４）一般式（Ｉ）で示される化合物と一般式（Ｖ）で示される化合物
（５）一般式（Ｉ）で示される化合物と一般式（ＶＩ）で示される化合物
（６）一般式（Ｉ）で示される化合物と一般式（ＶＩＩ）で示される化合物
（７）一般式（Ｉ）で示される化合物と一般式（ＶＩＩＩ）で示される化合物
（８）一般式（Ｉ）で示される化合物と一般式（ＩＸ）で示される化合物
(1) first compound represented by the general formula (I) and the compound represented by one general formula (II) (2) compound represented by the first compound represented by the general formula (I) and one general formula (III) (3 ) compound shown by a compound represented by the general formula (I) and one general formula (IV) (4) a compound shown by a compound represented by the general formula (I) and one general formula (V) (5) one general formula compounds represented by (I) a compound shown by a general formula (VI) (6) a compound shown by a compound represented by the general formula (I) and one general formula (VII) (7) one general formula compounds represented by (I) a compound shown by a general formula (VIII) (8) a compound represented by the compound shown by a general formula (I) and one general formula (IX)
（１）一般式（Ｉ）で示される化合物と一般式（ＩＩ）で示される化合物
（２）一般式（Ｉ）で示される化合物と一般式（ＩＩＩ）で示される化合物
（３）一般式（Ｉ）で示される化合物と一般式（ＩＶ）で示される化合物
（４）一般式（Ｉ）で示される化合物と一般式（Ｖ）で示される化合物
（５）一般式（Ｉ）で示される化合物と一般式（ＶＩ）で示される化合物
（６）一般式（Ｉ）で示される化合物と一般式（ＶＩＩ）で示される化合物
（７）一般式（Ｉ）で示される化合物と一般式（ＶＩＩＩ）で示される化合物
（８）一般式（Ｉ）で示される化合物と一般式（ＩＸ）で示される化合物。
(1) first compound represented by the general formula (I) and the compound represented by one general formula (II) (2) compound represented by the first compound represented by the general formula (I) and one general formula (III) (3 ) compound shown by a compound represented by the general formula (I) and one general formula (IV) (4) a compound shown by a compound represented by the general formula (I) and one general formula (V) (5) one general formula compounds represented by (I) a compound shown by a general formula (VI) (6) a compound shown by a compound represented by the general formula (I) and one general formula (VII) (7) one general formula compounds represented by (I) a compound shown by a general formula (VIII) (8) a compound represented by the compound shown by a general formula (I) and one general formula (IX).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23733496A JP3808139B2 (en) | 1996-08-20 | 1996-08-20 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23733496A JP3808139B2 (en) | 1996-08-20 | 1996-08-20 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1063020A JPH1063020A (en) | 1998-03-06 |
| JP3808139B2 true JP3808139B2 (en) | 2006-08-09 |
Family
ID=17013847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23733496A Expired - Fee Related JP3808139B2 (en) | 1996-08-20 | 1996-08-20 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3808139B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008257147A (en) * | 2006-06-13 | 2008-10-23 | Ricoh Co Ltd | Electrophotographic photoreceptor and method of manufacturing the same, and image forming apparatus, image forming method and process cartridge |
| US8951702B2 (en) | 2008-07-18 | 2015-02-10 | Fuji Electric Co., Ltd. | Charge transport material that is an ethylene compound, electrophotographic photoreceptor containing the charge transport material, and process for producing the electrophotographic photoreceptor |
-
1996
- 1996-08-20 JP JP23733496A patent/JP3808139B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH1063020A (en) | 1998-03-06 |
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