JP3947491B2 - Electrophotographic photoreceptor and image forming apparatus - Google Patents
Electrophotographic photoreceptor and image forming apparatus Download PDFInfo
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- JP3947491B2 JP3947491B2 JP2003134065A JP2003134065A JP3947491B2 JP 3947491 B2 JP3947491 B2 JP 3947491B2 JP 2003134065 A JP2003134065 A JP 2003134065A JP 2003134065 A JP2003134065 A JP 2003134065A JP 3947491 B2 JP3947491 B2 JP 3947491B2
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- photoreceptor
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- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
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- UDJWHGNSQWLKGR-UHFFFAOYSA-N n-methyl-4-[5-[4-(methylamino)phenyl]-1,3,4-oxadiazol-2-yl]aniline Chemical compound C1=CC(NC)=CC=C1C1=NN=C(C=2C=CC(NC)=CC=2)O1 UDJWHGNSQWLKGR-UHFFFAOYSA-N 0.000 description 1
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Images
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Description
【０００１】
【発明の属する技術分野】
本発明は、優れた電荷輸送能を有するケトン誘導体を含有し、静電式複写機、ファクシミリ、レーザービームプリンタまたはそれらの複合機等の画像形成装置に用いられる電子写真感光体に関する。
【０００２】
【従来の技術】
上記画像形成装置においては、光照射によって電荷を発生する電荷発生剤、発生した電荷を輸送する電荷輸送剤、およびこれらの物質が分散される層を構成する結着樹脂等からなる、いわゆる有機感光体が広く使用されている。そして、この感光体を駆動手段により一定方向に駆動し、その駆動方向に沿って設けられた帯電手段、露光手段、現像手段および転写手段により画像が形成される。転写後に感光体表面に残留したトナーは必要に応じてクリーニング手段によって除去される。この一連の画像形成操作において、感光体には露光手段の光源の波長領域に対して高感度であることが求められる。
【０００３】
ところで、有機感光体としては、大別して、電荷発生剤と電荷輸送剤とを同一の層中に含有させた単層型の感光層を備えたものと、電荷発生剤を含む電荷発生層と、電荷輸送剤を含む電荷輸送層とを積層した積層型の感光層を備えた感光体が一般的である。また上記積層型の感光層は、機械的強度の面から、電荷発生層よりも膜厚の厚い電荷輸送層を、感光体の最外層に配置するのが一般的である。
【０００４】
これらの感光体に使用される電荷輸送剤としては、正孔輸送性のものと電子輸送性のものとがあるが、現在知られている電荷輸送剤のうち、感光体に実用的な感度を付与しうるキャリヤ移動度の高いものは、その多くが正孔輸送性である。
【０００５】
そこで従来より電子輸送剤として、電子輸送能を向上させたものを使用することが検討されている。例えば特許文献1には一般式(C1)：
【０００６】
【化２】
で表される分子骨格を有する化合物を、特許文献2にはナフトキノン誘導体を、それぞれ電子輸送剤として使用することが提案されている。
【０００８】
しかしながら上記化合物は、帯電手段、転写手段のコロナ放電に伴って発生するオゾンやNOx等のガスに対して、耐性が乏しく、電子輸送能が低下するという問題点があった。
【０００９】
従って、従来の電子輸送剤を含有する感光層を有する感光体は、長時間使用による電気的特性、特に帯電性が不十分になり、画像形成した場合に画像濃度が低く、印刷物にかぶりが発生するという問題が生じる。
【００１０】
【特許文献１】
特開2001−66805号公報
【００１１】
【特許文献２】
特開平9-151157号公報
【００１２】
【発明が解決しようとする課題】
そこで、本発明の目的は、上記の技術的課題を解決し、従来に比べて耐ガス性に優れ、長時間の使用においても電気特性が低下しない電子写真感光体を提供することである。
【００１３】
本発明の他の目的は、画像濃度が高く、画像かぶりのない良好な画像を得ることができる画像形成装置を提供することである。
【００１４】
【課題を解決するための手段】
本発明者らは、上記課題を解決するために鋭意研究を重ねた結果、一般式(1)：
【００１５】
【化３】
（式中、R1はアルキル基、アリール基またはアルコキシカルボニル基、R2はアルキル基をそれぞれ示す。）
で表されるケトン誘導体（以下、ケトン誘導体(1)と記述する。）が、上記ナフトキノン誘導体、上記ジナフトキノン誘導体および上記一般式(3)で表される分子骨格を有する化合物等の従来の電子輸送剤よりも耐ガス性に優れているという新たな事実を見出し、本発明を完成するに至った。
【００１７】
ケトン誘導体(1)は、電子受容性が優れており、さらに結着樹脂との相溶性も良好で感光層中に均一に分散される。また、電荷発生剤とのマッチングに優れており、当該電荷発生剤からの電子注入が円滑に行われる。さらに、ケトン誘導体(1)は放電生成物であるオゾンやNOx等のガスに対して変性しない。従って、ケトン誘導体(1)は上記ガスに曝されても優れた電子輸送性を示し、電子写真感光体における電子輸送剤として好適である。
【００１８】
本発明の電子写真感光体は、支持基体上に感光層を設けたものであって、感光層がケトン誘導体(1)を含有することを特徴とする。
【００１９】
この電子写真感光体は、前述のように優れた特性を有するケトン誘導体(1)を感光層中に含有することから、残留電位が低く、高感度であるだけでなく、従来の電子輸送剤を含有する電子写真感光体よりも帯電性が高いという特徴を有する。
【００２０】
すなわち、ケトン誘導体(1)を含有する感光層は、低電界での電子輸送性に優れているとともに、耐ガス性が高く、感光層中で電子と正孔とが再結合する割合が低く、見掛けの電荷発生率が実際の値に近づく結果、電気特性が向上する。
【００２１】
本発明の画像形成装置は、上記本発明の電子写真感光体と、前記感光体を一定方向に駆動する駆動手段とを有し、前記感光体の駆動方向に沿って帯電手段、露光手段、現像手段および転写手段がこの順に設けられていることを特徴とする。このため、当該画像形成装置において、繰り返し画像形成を行っても画像かぶりのない良好な画像を得ることができる。
【００２２】
【発明の実施の形態】
（ケトン誘導体(1)）
上記一般式(1)中の置換基R1〜R2で定義された基の内、置換基群として示されたものの具体例は以下の通りである。
【００２３】
アルキル基としては、例えばメチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、s-ブチル基、t-ブチル基、n-ペンチル基、イソペンチル基、ネオペンチル基、ヘキシル基といった炭素数が１〜６の基などが上げられる。その中でも、メチル基およびエチル基が特に好ましい。
【００２４】
上記アルキル基は置換基を有していてもよく、具体的にはヒドロキシアルキル基、アルコキシアルキル基、モノアルキルアミノアルキル基、ジアルキルアミノアルキル基、ハロゲン置換アルキル基、アルコキシカルボニルアルキル基、カルボキシアルキル基、アルカノイルオキシアルキル基、アミノアルキル基などがあげられる。
【００２５】
アリール基としては、例えばフェニル基、ナフチル基、アントリル基、フェナントリル基などがあげられる。その中でもフェニル基が特に好ましい。
【００２６】
上記アリール基は置換基を有していてもよく、具体的には、例えばハロゲン原子、アミノ基、ヒドロキシ基、エステル化されていてもよいカルボキシル基、シアノ基などの他、前述と同様の炭素数1〜6の置換基を有してもよいアルキル基や炭素数1〜6の置換基を有してもよいアルコキシ基などがあげられる。なお、これらの置換基の置換位置については特に限定されない。
【００２７】
上記アルコキシカルボニル基としては、例えばメトキシカルボニル基、エトキシカルボニル基、プロポキシカルボニル基、イソプロポキシカルボニル基、ブトキシカルボニル基、ｔ−ブトキシカルボニル基、ペンチルオキシカルボニル基、ヘキシルオキシカルボニル基等の置換基末端のアルキル基が炭素数1〜6のものが上げられる。その中でもメトキシカルボニル基、エトキシカルボニル基が特に好ましい。
【００２８】
次に、ケトン誘導体(1)の合成方法の一例を以下に説明する。
【００２９】
反応式（I）：
【００３０】
【化４】
反応式（II）：
【００３２】
【化５】
上記の方法によりケトン誘導体(1)を効率よく得ることができる。
（電荷発生剤）
上記単層型もしくは積層型感光層に使用される電荷発生剤としては、例えば非晶質無機材料〔例えばa-シリコン、a-炭素など〕などの無機光導電材料の粉末、無金属フタロシアニン、金属（例えば、チタン、銅、アルミニウム、鉄、コバルト、ニッケル、インジウム、ガリウム、錫、亜鉛、バナジウム等）または金属酸化物（上記金属の酸化物でありTiO等）が配位したフタロシアニン等の、種々の結晶型を有する結晶からなるフタロシアニン系顔料、アゾ系顔料、ビスアゾ系顔料、ペリレン系顔料、アンサンスロン系顔料、インジゴ系顔料、トリフェニルメタン系顔料、スレン系顔料、トルイジン系顔料、ピラゾリン系顔料、キナクリドン系顔料、ジチオケトピロロピロール系顔料などの、従来公知の種々の顔料が挙げられる。上記の内、無金属フタロシアニン、チタニルフタロシアニン、ヒドロキシガリウムフタロシアニンを用いることが好ましい。電荷発生剤は、感光層が露光の波長域に感度を有するように、それぞれ単独で、あるいは2種以上を組み合わせて使用することができる。
（正孔輸送剤）
本発明に用いられる正孔輸送剤としては、従来公知の例えば、ベンジジン系化合物、フェニレンジアミン系化合物、ナフチレンジアミン系化合物、フェナントリレンジアミン系化合物、オキサジアゾール系化合物〔例えば2,5-ジ（4-メチルアミノフェニル）-1,3,4-オキサジアゾールなど〕、スチリル系化合物〔例えば9-（4-ジエチルアミノスチリル）アントラセンなど〕、ジスチリル化合物、カルバゾール系化合物〔例えばポリ-N-ビニルカルバゾールなど〕、ピラゾリン系化合物〔例えば1-フェニル-3-（p-ジメチルアミノフェニル）ピラゾリンなど〕、ヒドラゾン系化合物〔例えばジエチルアミノベンズアルデヒドジフェニルヒドラゾンなど〕、トリフェニルアミン系化合物、インドール系化合物、オキサゾール系化合物、イソオキサゾール系化合物、チアゾール系化合物、チアジアゾール系化合物、イミダゾール系化合物、ピラゾール系化合物、トリアゾール系化合物、ブタジエン系化合物、ピレン−ヒドラゾン系化合物、アクロレイン系化合物、カルバゾール−ヒドラゾン系化合物、キノリン−ヒドラゾン系化合物、スチルベン系化合物、スチルベン−ヒドラゾン系化合物、フェニレンジアミン系化合物、ジフェニレンジアミン系化合物、ナフチレンジアミン系化合物、フェナントリレンジアミン系化合物、チオフェン系化合物、縮合多環式化合物およびポリマー系正孔輸送剤〔例えば、有機ポリシランやポリヒドラゾンなど〕等が使用可能である。
【００３４】
本発明において、正孔輸送剤は1種のみを用いるほか、2種以上を混合して用いてもよい。また、ポリビニルカルバゾール等の成膜性を有する正孔輸送剤を用いる場合には、結着樹脂は必ずしも必要でない。
（電子受容体）
本発明の電子写真感光体においては、電子輸送剤である本発明のケトン誘導体(1)と共に、従来公知の電子受容体を感光層に含有させてもよい。具体例としては、ベンゾキノン誘導体、ジフェノキノン系化合物、ナフトキノン系化合物、マロノニトリル、チオピラン系化合物、テトラシアノエチレン、2,4,8-トリニトロチオキサントン、フルオレノン系化合物、ジニトロベンゼン、ジニトロアントラセン、ジニトロアクリジン、ニトロアントラキノン、無水こはく酸、無水マレイン酸、ジブロモ無水マレイン酸、2,4,7-トリニトロフルオレノンイミン系化合物、エチル化ニトロフルオレノンイミン系化合物、トリプトアントリン系化合物、トリプトアントリンイミン系化合物、アザフルオレノン系化合物、ジニトロピリドキナゾリン系化合物、チオキサンテン系化合物、2-フェニル-1,4-ベンゾキノン系化合物、2-フェニル-1,4-ナフトキノン系化合物、5,12-ナフタセンキノン系化合物、α-シアノスチルベン系化合物、4'-ニトロスチルベン系化合物、ならびに、ベンゾキノン系化合物の陰イオンラジカルとカチオンとの塩などの電子吸引性化合物があげられる。本発明において、電子受容体は1種のみを用いるほか、2種以上を混合して用いてもよい。
（結着樹脂）
前記各成分を分散させるための結着樹脂は、従来、感光層に使用されている種々の樹脂を使用することができる。例えばスチレン系重合体、スチレン−ブタジエン共重合体、スチレン−アクリロニトリル共重合体、スチレン−マレイン酸共重合体、アクリル系重合体、スチレン−アクリル系共重合体、ポリエチレン、エチレン−酢酸ビニル共重合体、塩素化ポリエチレン、ポリ塩化ビニル、ポリプロピレン、塩化ビニル−酢酸ビニル共重合体、ポリエステル、ポリアミド、ポリカーボネート、ポリアリレート、ポリスルホン、ジアリルフタレート樹脂、ケトン樹脂、ポリビニルブチラール樹脂、ポリエーテル樹脂などの熱可塑性樹脂や、シリコーン樹脂、エポキシ樹脂、フェノール樹脂、尿素樹脂、メラミン樹脂、不飽和ポリエステル、アルキッド樹脂、ポリウレタン、その他架橋性の熱硬化性樹脂、さらにエポキシ−アクリレート、ウレタン−アクリレートなどの光硬化性樹脂などが使用可能である。
（その他の材料）
感光層には、前記各成分のほかに、電子写真特性に悪影響を与えない範囲で、従来公知の種々の添加剤、例えば酸化防止剤、ラジカル捕捉剤、一重項クエンチャー、紫外線吸収剤等の劣化防止剤、軟化剤、可塑剤、表面改質剤、増量剤、増粘剤、分散安定剤、ワックス、アクセプター、ドナー等を配合することができる。また、感光層の感度を向上させるために、例えばテルフェニル、ハロナフトキノン類、アセナフチレン等の公知の増感剤を電荷発生剤と併用してもよい。
（感光層）
本発明の電子写真感光体は、ケトン誘導体(1)を電子輸送剤として含有する感光層を支持基体上に設けたものである。本発明の電子写真感光体は、単層型および積層型のいずれにも適用できる。
【００３５】
このうち単層型感光体は、支持基体上に、少なくとも電子輸送剤であるケトン誘導体(1)と電荷発生剤と結着樹脂とを含有する光導電層単独で構成されるものである。
【００３６】
この単層型の感光層は、単独の構成で正負いずれの帯電にも対応できるが、有害なオゾンの発生を促す負極性コロナ放電を用いる必要のない、正帯電型で使用するのが好ましい。この単層型感光体は、層構成が簡単で生産性に優れていること、感光層の被膜欠陥が発生するのを抑制できること、正負いずれの帯電型にも使用できること、層を形成する際の皮膜欠陥を抑制できること、層間の界面が少ないので光学的特性を向上できること等の利点を有する。
【００３７】
さらに、電子輸送剤であるケトン誘導体(1)を正孔輸送性に優れた正孔輸送剤と併用した単層型の感光体は、前述のように、ケトン誘導体(1)と正孔輸送剤との相互作用が生じないため、両輸送剤を高濃度で同一の感光層中に含有させても、電子輸送および正孔輸送がそれぞれ効率よく行うことができ、より高感度の感光体を得ることができる。また、ケトン誘導体(1)とともに電子受容体を含有させた単層型感光体は、電子輸送性能をより一層向上することができ、より高感度の感光体を得ることができる。
【００３８】
一方、積層型感光体は、支持基体上に電荷発生剤を含有する電荷発生層と電荷輸送剤を含有する電荷輸送層とをこの順で、あるいは逆の順で積層することで構成される。また、電荷発生剤とともに電荷輸送剤を含有させた光導電層を、電荷輸送層、電荷発生層と組み合わせても良い。ケトン誘導体(1)は上記電荷輸送層または光導電層に含有させることができる。但し、電荷発生層は電荷輸送層に比べて膜圧がごく薄いため、その保護のためには支持基体上に電荷発生層を形成し、その上に電荷輸送層または光導電層を形成するのが好ましい。
【００３９】
積層型感光体は、電荷発生層と電荷輸送層との形成順序と、電荷輸送層中で使用する電荷輸送剤の種類とによって、正負いずれの帯電型となるかが選択される。例えば、支持基体上に電荷発生層を形成し、その上に電荷輸送層を形成した層構成において、電荷輸送層中の電荷輸送剤としてケトン誘導体(1)のような電子輸送剤を使用したときは、正帯電型の感光体になる。この場合、電荷発生層には正孔輸送剤や電子輸送剤を含有させてもよい。ここで、前記電荷輸送層に電子受容体を含有させた場合は、電子輸送性が向上するため、より高感度の積層感光体を得ることができる。
【００４０】
なお、上記の層構成において、電荷輸送層中の電荷輸送剤として正孔輸送剤を使用したときは負帯電型の感光体になる。この場合、電荷発生層にはケトン誘導体(1)や電子受容体を含有させてもよい。
【００４１】
以上に述べた積層型感光体は、電荷発生、電荷輸送といった機能を各層に分離しているので、構成材料の無駄が少なく、感度を向上させ易いという利点を有する。
（支持基体）
前記感光層が形成される支持基体としては、導電性を有する種々の材料を使用することができ、例えば鉄、アルミニウム、銅、スズ、白金、銀、バナジウム、モリブデン、クロム、カドミウム、チタン、ニッケル、パラジウム、インジウム、ステンレス鋼、真鍮等の金属単体や、前記金属が蒸着またはラミネートされた樹脂材料、カーボン粉末などの導電性フィラーが分散された樹脂材料、導電性高分子材料、ヨウ化アルミニウム、酸化スズ、酸化インジウム等で被覆されたガラス等が挙げられる。
【００４２】
支持基体の形状は、使用する画像形成装置の構造に合わせて、シート状、ベルト状、ドラム状等のいずれであってもよく、基体自体が導電性を有するか、あるいは基体の表面が導電性を有していればよい。また、支持基体は、使用に際して十分な機械的強度を有するものが好ましい。
（感光層の形成）
感光層は、例えばプラズマCVD法、光CVD法等の化学蒸着法、スパッタリング法、真空蒸着法、イオンプレーティング法等の物理蒸着法など、従来公知の種々の気相成長法、または塗布法よって形成することができる。
【００４３】
この内、塗布法については以下のようにして形成すれば良い。
【００４４】
単層型感光層においては、結着樹脂100重量部に対して、電荷発生剤を0.1〜50重量部、特に0.5〜30重量部の割合で、それぞれ含有させるのが好ましい。ケトン誘導体(1)（電子輸送剤）は、結着樹脂100重量部に対して5〜100重量部、特に10〜80重量部の割合で含有させるのが好ましい。また、正孔輸送剤を含有させる場合は5〜500重量部、特に25〜200重量部の割合で、それぞれ含有させるのが好ましい。電子受容体を含有させる場合、電子受容体の割合を結着樹脂の100重量部に対して0.1〜40重量部、特に0.5〜20重量部とするのが好ましい。また、電子輸送剤と正孔輸送剤とを併用する場合、その総量は結着樹脂100重量部に対して20〜500重量部、特に30〜200重量部が好ましい。
【００４５】
単層型感光層の厚みは5〜100μm、特に10〜50μm程度が好ましい。
【００４６】
積層型感光層のうち電荷発生層においては、結着樹脂100重量部に対して、電荷発生剤を5〜1000重量部、特に30〜500重量部の割合で含有させるのが好ましい。この電荷発生層に電荷輸送剤を含有して光導電層とする場合には、結着樹脂100重量部に対して、ケトン誘導体(1)を含有させる場合は1〜200重量部、特に5〜100重量部の割合で含有させるのが好ましい。正孔輸送剤を含有させる場合は、当該正孔輸送剤を1〜500重量部、特に25〜200重量部の割合で含有させるのが好ましい。また、電子受容体を含有させる場合は1〜200重量部、特に5〜100重量部の割合で含有させるのが好ましい。電子受容体と正孔輸送剤とを併用する場合、その総量は結着樹脂100重量部に対して10〜500重量部、特に30〜200重量部が好ましい。
【００４７】
また電荷輸送層においては、結着樹脂100重量部に対して、正孔輸送剤を含有させる場合は5〜200重量部、特に10〜80重量部の割合で、ケトン誘導体(1)を含有させる場合は10〜500重量部、特に25〜100重量部の割合で、電子受容体を含有させる場合は、当該電子輸送剤を0.1〜250重量部、特に1〜150重量部の割合でそれぞれ含有させるのが好ましい。また、電子受容体と正孔輸送剤とを併用する場合、その総量は結着樹脂100重量部に対して10〜500重量部、特に30〜200重量部が好ましい。
【００４８】
積層型感光層の厚みは、電荷発生層が0.01〜5μm、特に0.1〜3μm程度、電荷輸送層が2〜100μm、特に5〜50μm程度が好ましい。
【００４９】
単層型感光体においては、支持基体と感光層との間に、また積層型感光体においては、支持基体と電荷発生層との間、支持基体と電荷輸送層との間または電荷発生層と電荷輸送層との間に、感光体の特性を阻害しない範囲でバリア層が形成されていてもよい。また、感光体の表面には、保護層が形成されていてもよい。
【００５０】
感光体を構成する各層を、塗布の方法により形成する場合には、前記例示の電荷発生剤、電荷輸送剤、結着樹脂などを、前述したテトラヒドロフランなどの有機溶媒とともに、公知の方法、例えば、ロールミル、ボールミル、アトライタ、ペイントシェーカーあるいは超音波分散器などを用いて分散混合して塗工液を調整し、これを公知の手段により塗布、乾燥すればよい。
【００５１】
塗工液を作るための有機溶媒としては、例えばメタノール、エタノール、イソプロパノール、ブタノールなどのアルコール類、n-ヘキサン、オクタン、シクロヘキサンなどの脂肪族系炭化水素、ベンゼン、トルエン、キシレンなどの芳香族炭化水素、ジクロロメタン、ジクロロエタン、四塩化炭素、クロロベンゼンなどのハロゲン化炭化水素、ジメチルエーテル、ジエチルエーテル、テトラヒドロフラン、1,4-ジオキサン、1,3-ジオキサン、エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテルなどのエーテル類、アセトン、メチルエチルケトン、シクロヘキサノンなどのケトン類、酢酸エチル、酢酸メチルなどのエステル類、ジメチルホルムアルデヒド、ジメチルホルムアミド、ジメチルスルホキシド等があげられる。これらの溶剤は単独でまたは２種以上を混合して用いられる。
【００５２】
さらに、電荷輸送剤や電荷発生剤の分散性、感光層表面の平滑性をよくするため、塗工液には界面活性剤、レベリング剤などを添加してもよい。
（画像形成装置）
図1は本発明で実施した画像形成装置の一例を模式的に示したものである。1は上述の電子写真感光体（支持基体10上に感光層11が形成されている。）であって、その軸心13が駆動手段14とギア、プーリを介して接続されており一方向（矢印Aの向き）に定速度で回転するようになっている。この感光体1の周辺にはその駆動方向、つまり回転方向に沿って主帯電手段2、露光手段3、現像手段4、転写手段5がこの順序で設けられている。また、図1に示されるように必要に応じて分離手段6、除電手段7、クリーニング手段9が設けられていてもよい。
【００５３】
さらに、本発明の画像形成装置には、定着手段12が設置されており、トナー像が転写された転写媒体8に対して、トナー像の定着を施すようになっている。
【００５４】
画像の形成の際は、まず帯電手段2により感光体1表面は一様に帯電される。次いで、露光手段3より露光軸31に沿って感光体1表面が露光され、原稿画像に対応した静電潜像が形成される。当該画像形成装置は上述の電子写真感光体を用いているので、感光体１の接地部に対する電位（以下、表面電位と記述する。）は素早く明電位の値まで低下する。そして、露光されなかった非画像領域は表面電位の低下がほとんど無く暗電位の値で安定する。
【００５５】
その後、現像手段4により静電潜像に対応する部分にトナーが付着して現像される。そして、転写手段5により、搬送（矢印Bの向き）されてくる転写媒体8上に感光体1表面のトナー像が転写される。転写後の転写媒体8は、分離手段6で感光体1から分離された後、定着手段12によりトナー定着される。
【００５６】
転写後、転写媒体8に転写しきれず感光体1表面に残ったトナーは、クリーニング手段9によって除去される。その後、感光体1表面の残留電位は除電手段7からの除電光71により除去され、再び帯電手段2により帯電される。
【００５７】
帯電手段2としては従来公知の例えば、感光体1の表面に近接して設けられるチャージワイヤーに高電圧を掛けてコロナ放電を行う方法や、導電性ローラーや帯電ブラシなどの帯電部材を感光体1表面に接触させて感光体１に電荷を与える方法等が適用される。主帯電部での表面電位を一定に保つために、帯電部材を感光体１表面に接触させる方法または、前記主帯電器のチャージワイヤーと感光体１との間にグリッド電極を設けて、コロナ放電を行う方法を用いることが好ましい。
【００５８】
帯電手段２から感光体１に印加される主帯電電圧は、感光体１やトナーの特性、現像条件等によって異なるが、例えば一般的な正帯電型感光体の場合、感光体１表面の接地部に対する電位差が+300V〜+1000Vになるように設定すればよい。
【００５９】
露光手段３としては、感光体１が感度を示す波長のレーザー光が一般的に用いられる。具体的には、電荷発生剤が吸収を示す波長の光を用いればよい。例えば、電荷発生剤としてフタロシアニン系顔料を用いるの場合は、波長が600nm〜850nm程度、ペリレン系顔料では400〜600nm程度、ビスアゾ系顔料では400〜700nm程度のレーザー光が用いられる。
【００６０】
露光量は、できる限り明電位が低い値になるよう設定される方がよい。具体的には、感光体1の明電位を、主帯電された感光体1の接地部に対する電位と同極性とし、加えて、好ましくは0〜500V、更に好ましくは0〜300Vにするよう、露光量が設定されるのがよい。
【００６１】
現像手段4としては、従来公知の接触または非接触現像装置を用いることができる他、乾式、湿式のいずれの方法によるものでもよい。現像手段4に用いられる現像剤は、一成分系、二成分系のどちらでもよい。
【００６２】
転写手段5としては、従来公知の接触転写あるいは非接触転写方式のいずれも適用可能である。具体的には、チャージャー、ローラー、ブラシ、プレート等により、転写媒体8を介して感光体1に転写電圧が印加される。
【００６３】
分離手段6としては、帯電手段2と同様に、チャージワイヤーによるコロナ放電によるもの、導電性ローラーを用いるもの等が使用でき、中でもコロナ放電によるものが好適に用いられる。分離手段6により感光体1に印加される分離電圧は、一般的に交流である。
【００６４】
除電手段7を設ける場合は、従来公知の例えば、LEDアレイ、蛍光管などの除電ランプを使用することができる。当該除電ランプは、感光体1が感度を持つ波長で、感光体１表面の残留電荷を除去できるのに十分な光量を照射するものを用いれば良い。
【００６５】
クリーニング手段9を設ける場合は、従来公知の例えばブレード方式、ファーブラシ方式、ローラクリーニング方式等が簡単な機構でトナー除去効率の良いものとして用いることができる。
【００６６】
定着手段12としては、従来公知の例えば熱定着、圧力定着、熱圧力定着、フラッシュ定着などを用いれば良い。
【００６７】
【実施例】
以下、本発明を合成例、実施例および比較例に基づいて説明する。
（ケトン誘導体(1)の合成）
［合成例１−１］
3,5-ジ-t-ブチル-4-ヒドロキシベンズアルデヒド１０g（０．０４３mol）およびR-(-)-２-フェニルグリシン塩酸塩８．７９g（０．０４３mol）を３００ｍｌフラスコに入れ、ピリジン１５０ｍｌを加え加熱還流を3時間行った。反応液を冷却後、希塩酸水溶液３００ｍｌに注ぎ、析出固体をろ過別した。固体をクロロホルム150mlに溶解し、水洗を繰り返し、有機層を無水硫酸マグネシウムにて乾燥後、有機層を留去した。
【００６８】
得られた赤色残渣を再度クロロホルム１００ｍｌに溶解し、酸化銀２０ｇを加え一晩室温にて攪拌を行った。酸化銀をろ別し、有機層をシリカゲルカラムクロマトグラフィー（クロロホルム展開）にて精製を行い、
目的物（以下、ケトン誘導体(1-1)と記述する。）８．１g（収率49.6%）を得た。
下記一般式(1-1)：
【００６９】
【化６】
上記、ケトン誘導体(1-1)の赤外線吸収スペクトルを図2に示す。
［合成例１−２］
（実施例１−１と同様に、Ｌ−アラニンメチルエステル塩酸塩６ｇ（０．０４３mol）を使用して目的物（以下、ケトン誘導体(1-2)と記述する。）５．５g（収率４０%）を得た。を得た。）
下記一般式(1-2)：
【００７１】
【化７】
上記、ケトン誘導体(1-2)の赤外線吸収スペクトルを図3に示す。
［合成例１−３］
（実施例１−１と同様に使用原料としてL-アラニンエチルエステル塩酸塩6.6ｇ（0.043mol）を使用して目的物（以下、ケトン誘導体(1-3)と記述する。）５．６g（収率３９%）を得た。）
下記一般式(1-3)：
【００７３】
【化８】
上記、ケトン誘導体(1-3)の赤外線吸収スペクトルを図４に示す。
［合成例１−４］
（実施例１−１同様にジメチルアミノマロネイト塩酸塩7.9ｇ（0.043mol）を用いて目的物（以下、ケトン誘導体(1-4)と記述する。）6.53g（収率42%）を得た。）
下記一般式(1-4)：
【００７５】
【化９】
上記、ケトン誘導体(1-4)の赤外線吸収スペクトルを図5に示す。
［合成例１−５］
（実施例１−１と同様にジメチルアミノマロネイト塩酸塩9.1ｇ（0.043mol）を用いて目的物（以下、ケトン誘導体(1-5)と記述する。）6.8g（収率40.6%）を得た。）
下記一般式(1-5)：
【００７７】
【化１０】
上記、ケトン誘導体(1-5)の赤外線吸収スペクトルを図6に示す。
（単層型電子写真感光体の作製）
［実施例１−１］
電荷発生剤としてX型無金属フタロシアニン5重量部および結着樹脂としてポリカーボネート100重量部、溶媒としてテトラヒドロフラン800重量部、正孔輸送剤としてN,N,N',N'-テトラキス（3-メチルフェニル）-3,3'-ジアミノベンジジン50重量部および電子輸送剤であるケトン誘導体(1-1)30重量部をボールミルにて50時間混合、分散させて単層感光体用の塗布液を作製した。次いで、この塗布液をアルミニウムシート上にワイヤーバーを用いて塗布し、100℃で１時間乾燥させて、膜厚が20μmの感光層を形成させ、単層型感光体を作製した。
［実施例１−２］
ケトン誘導体(1-1)に代えてケトン誘導体(1-2)を用いる他は、実施例1-1と同様にして単層型感光体を作製した。
［実施例１−３］
ケトン誘導体(1-1)に代えてケトン誘導体(1-3)を用いる他は、実施例1-1と同様にして単層型感光体を作製した。
［実施例１−４］
ケトン誘導体(1-1)に代えてケトン誘導体(1-4)を用いる他は、実施例1-1と同様にして単層型感光体を作製した。
［実施例１−５］
ケトン誘導体(1-1)に代えてケトン誘導体(1-5)を用いる他は、実施例1-1と同様にして単層型感光体を作製した。
［実施例１−６］
ケトン誘導体(1-1)に代えてケトン誘導体(1-6)を用いる他は、実施例1-1と同様にして単層型感光体を作製した。
［比較例１−１］
ケトン誘導体(1-1)に代えて一般式(C1-1)：
【００７９】
【化１１】
（ｔ-Buはt-ブチル基を示す。）
で表される化合物を用いる他は、実施例1-1と同様にして単層型感光体を作製した。
［比較例１−２］
ケトン誘導体(1-1)に代えて一般式(C2-1)：
【００８１】
【化１２】
で表される化合物を用いる他は、実施例1-1と同様にして単層型感光体を作製した。
（感光体の評価）
上記電子写真感光体を静電式複写装置（単層感光体の場合は京セラミタ社製KM-4530を使用した。）に設置して、表面電位が単層型感光体の場合は+700V、積層型感光体の場合は-700Vとなるようにグリッド電圧を設定しつつ帯電させた。次いで、オゾン雰囲気(5ppm)に5時間暴露して、暴露前に設定したグリッド電圧と同じ条件での表面電位を測定した。
【００８３】
さらに、オゾン暴露前後の表面電位の変化量(V)を求めて、電子写真感光体の耐オゾン性を評価した。例えば、オゾン暴露前の表面電位が+850Vであって、暴露後の表面電位が+740Vであれば、評価は-110Vとなる。オゾン暴露前後の表面電位の変化量は、X型無金属フタロシアニンを用いた単層型感光体では±100V以内、好ましくは±60V以内であればい（暴露後の表面電位の低下量または上昇量が上記値の絶対値よりも小さければよい）。変化量が大きくなるほど、電子写真感光体の耐オゾン性が低いといえる。単層型感光体の結果を表1に示す。
【００８４】
【表１】
表1より、実施例1-1、1-3および1-5の単層型感光体は、比較例1-1および1-2の単層型感光体と比較して、オゾン暴露前後の表面電位の変化量が小さいことが確認された。
（画像評価）
実施例、比較例で得られた感光体を静電式複写機（京セラミタ社製KM-4530を使用した。）に搭載して初期設定後、1000回単発コピーを行った。その後、画像を出力して、白紙部分の画像かぶりおよびべた黒部分の画像濃度を目視にて確認した。なお、静電式複写機は以下の設定とした。
・帯電：スコロトロン（初期表面電位約700V）
・露光：レーザー光
・現像：反転現像
・転写：転写チャージャー
・クリーニング：クリーニングブレード方式
・除電：除電ランプ（LED）
・分離：チャージワイヤー
・定着：熱圧力定着
結果として実施例1-1〜1-6で得られた単層型感光体を使用した場合は、画像かぶりの発生がなく、べた黒部分でも掠れのない十分な濃度の画像が得られた。一方、比較例1-1および1-2の単層型感光体を使用した場合は、画像かぶりが発生し、べた黒部分が掠れて十分な濃度の画像が得られなかった。
【００８６】
【発明の効果】
以上記述したように、本発明の電子写真感光体は、ケトン誘導体(1)を含有することから、耐ガス性に優れており、長時間の使用においても電気特性が低下しない。
【００８７】
また、本発明の画像形成装置は、上記電子写真感光体を用いることから、繰り返し画像形成を行っても画像濃度が高く、画像かぶりのない良好な画像を得ることができる。
【図面の簡単な説明】
【図１】本発明の画像形成装置を示す図である。
【図２】ケトン誘導体(1-1)の赤外線吸収スペクトルを示す図である。
【図３】ケトン誘導体(1-2)の赤外線吸収スペクトルを示す図である。
【図４】ケトン誘導体(1-4)の赤外線吸収スペクトルを示す図である。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an electrophotographic photoreceptor that contains a ketone derivative having an excellent charge transporting ability and is used in an image forming apparatus such as an electrostatic copying machine, a facsimile, a laser beam printer, or a composite machine thereof.
[0002]
[Prior art]
In the image forming apparatus, a so-called organic photosensitizer comprising a charge generating agent that generates a charge upon irradiation with light, a charge transporting agent that transports the generated charge, and a binder resin that constitutes a layer in which these substances are dispersed. The body is widely used. The photosensitive member is driven in a fixed direction by a driving unit, and an image is formed by a charging unit, an exposure unit, a developing unit, and a transfer unit provided along the driving direction. The toner remaining on the surface of the photoreceptor after the transfer is removed by a cleaning unit as necessary. In this series of image forming operations, the photosensitive member is required to be highly sensitive to the wavelength region of the light source of the exposure unit.
[0003]
By the way, as an organic photoreceptor, broadly, those having a single-layer type photosensitive layer containing a charge generating agent and a charge transport agent in the same layer, a charge generating layer containing a charge generating agent, A photoreceptor having a laminated photosensitive layer in which a charge transport layer containing a charge transport agent is laminated is generally used. In the laminated photosensitive layer, from the viewpoint of mechanical strength, a charge transport layer having a thickness larger than that of the charge generation layer is generally disposed in the outermost layer of the photoreceptor.
[0004]
The charge transport agents used in these photoreceptors include those having a hole transporting property and those having an electron transporting property. Among currently known charge transporting agents, practical sensitivity is expected for the photoreceptor. Many of the high carrier mobility that can be imparted have hole transportability.
[0005]
Therefore, it has been studied to use an electron transport agent having improved electron transport ability. For example,
[0006]
[Chemical 2]
Patent Document 2 proposes the use of a compound having a molecular skeleton represented by the formula: naphthoquinone derivatives as electron transport agents.
[0008]
However, the above compound has a problem that it has poor resistance to gases such as ozone and NOx generated by corona discharge of the charging means and transfer means, and the electron transport ability is lowered.
[0009]
Therefore, a photoreceptor having a photosensitive layer containing a conventional electron transport agent has insufficient electrical characteristics, particularly chargeability after long-term use, and the image density is low when an image is formed, and the printed matter is fogged. Problem arises.
[0010]
[Patent Document 1]
Japanese Patent Laid-Open No. 2001-66805
[0011]
[Patent Document 2]
JP-A-9-151157
[0012]
[Problems to be solved by the invention]
SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide an electrophotographic photosensitive member that solves the above technical problems and has excellent gas resistance as compared with the prior art and does not deteriorate in electrical characteristics even when used for a long time.
[0013]
Another object of the present invention is to provide an image forming apparatus capable of obtaining a good image having a high image density and no image fog.
[0014]
[Means for Solving the Problems]
As a result of intensive studies to solve the above problems, the present inventors have obtained general formula (1):
[0015]
[Chemical 3]
(Where R 1 Is an alkyl group, aryl group or alkoxycarbonyl group, R 2 Each represents an alkyl group. )
Is a conventional derivative such as a compound having a molecular skeleton represented by the above naphthoquinone derivative, the above dinaphthoquinone derivative, and the above general formula (3). The present inventors have found a new fact that the gas resistance is superior to that of the transport agent, and have completed the present invention.
[0017]
The ketone derivative (1) has excellent electron acceptability, and also has good compatibility with the binder resin and is uniformly dispersed in the photosensitive layer. Moreover, it is excellent in matching with the charge generating agent, and electrons are smoothly injected from the charge generating agent. Further, the ketone derivative (1) is not denatured with respect to gases such as ozone and NOx which are discharge products. Therefore, the ketone derivative (1) exhibits excellent electron transport properties even when exposed to the above gas, and is suitable as an electron transport agent in an electrophotographic photoreceptor.
[0018]
The electrophotographic photosensitive member of the present invention is obtained by providing a photosensitive layer on a support substrate, and the photosensitive layer contains a ketone derivative (1).
[0019]
Since this electrophotographic photoreceptor contains the ketone derivative (1) having excellent characteristics as described above in the photosensitive layer, it has not only a low residual potential and high sensitivity, but also a conventional electron transport agent. It has a feature that the charging property is higher than that of the electrophotographic photosensitive member to be contained.
[0020]
That is, the photosensitive layer containing the ketone derivative (1) is excellent in electron transport property in a low electric field, has high gas resistance, and has a low rate of recombination of electrons and holes in the photosensitive layer. As a result of the apparent charge generation rate approaching the actual value, the electrical characteristics are improved.
[0021]
An image forming apparatus according to the present invention includes the electrophotographic photosensitive member according to the present invention and a driving unit that drives the photosensitive member in a certain direction. The means and the transfer means are provided in this order. For this reason, in the image forming apparatus, a good image without image fogging can be obtained even if image formation is repeated.
[0022]
DETAILED DESCRIPTION OF THE INVENTION
(Ketone derivative (1))
Substituent R in the above general formula (1) 1 ~ R 2 Specific examples of those shown as the substituent group among the groups defined in (1) are as follows.
[0023]
Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, and hexyl. Examples thereof include groups having 1 to 6 carbon atoms such as groups. Among these, a methyl group and an ethyl group are particularly preferable.
[0024]
The alkyl group may have a substituent, specifically a hydroxyalkyl group, an alkoxyalkyl group, a monoalkylaminoalkyl group, a dialkylaminoalkyl group, a halogen-substituted alkyl group, an alkoxycarbonylalkyl group, a carboxyalkyl group. Alkanoyloxyalkyl group, aminoalkyl group and the like.
[0025]
Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, and a phenanthryl group. Of these, a phenyl group is particularly preferred.
[0026]
The aryl group may have a substituent. Specifically, for example, a halogen atom, an amino group, a hydroxy group, a carboxyl group that may be esterified, a cyano group, etc. Examples thereof include an alkyl group which may have a substituent of 1 to 6 and an alkoxy group which may have a substituent of 1 to 6 carbon atoms. In addition, the substitution position of these substituents is not particularly limited.
[0027]
Examples of the alkoxycarbonyl group include, for example, a terminal end of a substituent such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, a butoxycarbonyl group, a t-butoxycarbonyl group, a pentyloxycarbonyl group, and a hexyloxycarbonyl group. An alkyl group having 1 to 6 carbon atoms is raised. Of these, a methoxycarbonyl group and an ethoxycarbonyl group are particularly preferable.
[0028]
Next, an example of a method for synthesizing the ketone derivative (1) will be described below.
[0029]
Reaction formula (I):
[0030]
[Formula 4]
Reaction formula (II):
[0032]
[Chemical formula 5]
The ketone derivative (1) can be obtained efficiently by the above method.
(Charge generator)
Examples of the charge generating agent used in the single layer type or multilayer type photosensitive layer include powders of inorganic photoconductive materials such as amorphous inorganic materials (for example, a-silicon, a-carbon, etc.), metal-free phthalocyanines, metals (For example, titanium, copper, aluminum, iron, cobalt, nickel, indium, gallium, tin, zinc, vanadium, etc.) or various phthalocyanines coordinated with metal oxides (such as the above metal oxides such as TiO) Phthalocyanine pigments, azo pigments, bisazo pigments, perylene pigments, ansanthrone pigments, indigo pigments, triphenylmethane pigments, selenium pigments, toluidine pigments, pyrazoline pigments composed of crystals having the following crystal types: And various conventionally known pigments such as quinacridone pigments and dithioketopyrrolopyrrole pigments. Of the above, it is preferable to use metal-free phthalocyanine, titanyl phthalocyanine, and hydroxygallium phthalocyanine. The charge generating agents can be used alone or in combination of two or more so that the photosensitive layer has sensitivity in the exposure wavelength region.
(Hole transport agent)
Examples of the hole transporting agent used in the present invention include conventionally known benzidine compounds, phenylenediamine compounds, naphthylenediamine compounds, phenanthrylenediamine compounds, oxadiazole compounds [for example, 2,5- Di (4-methylaminophenyl) -1,3,4-oxadiazole etc.], styryl compounds [eg 9- (4-diethylaminostyryl) anthracene etc.], distyryl compounds, carbazole compounds [eg poly-N- Vinylcarbazole, etc.], pyrazoline compounds (eg, 1-phenyl-3- (p-dimethylaminophenyl) pyrazoline, etc.), hydrazone compounds (eg, diethylaminobenzaldehyde diphenylhydrazone, etc.), triphenylamine compounds, indole compounds, oxazole Compounds, isoxazole compounds , Thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds, triazole compounds, butadiene compounds, pyrene-hydrazone compounds, acrolein compounds, carbazole-hydrazone compounds, quinoline-hydrazone compounds, stilbene compounds , Stilbene-hydrazone compounds, phenylenediamine compounds, diphenylenediamine compounds, naphthylenediamine compounds, phenanthrenediamine compounds, thiophene compounds, condensed polycyclic compounds and polymer hole transport agents [for example, Organic polysilane, polyhydrazone, etc.) can be used.
[0034]
In the present invention, the hole transport agent may be used alone or in combination of two or more. Further, when a hole transporting agent having film forming properties such as polyvinyl carbazole is used, the binder resin is not necessarily required.
(Electron acceptor)
In the electrophotographic photoreceptor of the present invention, a conventionally known electron acceptor may be contained in the photosensitive layer together with the ketone derivative (1) of the present invention which is an electron transport agent. Specific examples include benzoquinone derivatives, diphenoquinone compounds, naphthoquinone compounds, malononitrile, thiopyran compounds, tetracyanoethylene, 2,4,8-trinitrothioxanthone, fluorenone compounds, dinitrobenzene, dinitroanthracene, dinitroacridine, nitro Anthraquinone, succinic anhydride, maleic anhydride, dibromomaleic anhydride, 2,4,7-trinitrofluorenone imine compound, ethylated nitrofluorenone imine compound, tryptoanthrin compound, tryptoanthrin imine compound, aza Fluorenone compounds, dinitropyridoquinazoline compounds, thioxanthene compounds, 2-phenyl-1,4-benzoquinone compounds, 2-phenyl-1,4-naphthoquinone compounds, 5,12-naphthacenequinone compounds, α- Cyanos Examples thereof include electron-withdrawing compounds such as tilbene compounds, 4′-nitrostilbene compounds, and salts of anion radicals and cations of benzoquinone compounds. In the present invention, the electron acceptor may be used alone or in combination of two or more.
(Binder resin)
As the binder resin for dispersing each component, various resins conventionally used in the photosensitive layer can be used. For example, styrene polymer, styrene-butadiene copolymer, styrene-acrylonitrile copolymer, styrene-maleic acid copolymer, acrylic polymer, styrene-acrylic copolymer, polyethylene, ethylene-vinyl acetate copolymer , Chlorinated polyethylene, polyvinyl chloride, polypropylene, vinyl chloride-vinyl acetate copolymer, polyester, polyamide, polycarbonate, polyarylate, polysulfone, diallyl phthalate resin, ketone resin, polyvinyl butyral resin, polyether resin, etc. Silicone resin, epoxy resin, phenolic resin, urea resin, melamine resin, unsaturated polyester, alkyd resin, polyurethane, other cross-linkable thermosetting resin, epoxy-acrylate, urethane-acrylate Such as photocurable resins, such bets are available.
(Other materials)
In the photosensitive layer, in addition to the above-mentioned components, various conventionally known additives such as an antioxidant, a radical scavenger, a singlet quencher, an ultraviolet absorber, etc., as long as the electrophotographic characteristics are not adversely affected. Deterioration inhibitors, softeners, plasticizers, surface modifiers, extenders, thickeners, dispersion stabilizers, waxes, acceptors, donors, and the like can be blended. In order to improve the sensitivity of the photosensitive layer, a known sensitizer such as terphenyl, halonaphthoquinones, and acenaphthylene may be used in combination with the charge generator.
(Photosensitive layer)
The electrophotographic photoreceptor of the present invention is obtained by providing a photosensitive layer containing a ketone derivative (1) as an electron transport agent on a support substrate. The electrophotographic photosensitive member of the present invention can be applied to both a single layer type and a laminated type.
[0035]
Among these, the single-layer type photoreceptor is constituted by a photoconductive layer alone containing at least a ketone derivative (1) as an electron transport agent, a charge generating agent, and a binder resin on a supporting substrate.
[0036]
This single-layer type photosensitive layer can handle both positive and negative charges with a single structure, but it is preferable to use a positively charged type that does not require negative corona discharge that promotes the generation of harmful ozone. This single layer type photoreceptor has a simple layer structure and excellent productivity, can suppress the occurrence of film defects in the photosensitive layer, can be used for both positive and negative charge types, and can be used for forming a layer. There are advantages such as the ability to suppress film defects and the improvement of optical characteristics since there are few interfaces between layers.
[0037]
Furthermore, as described above, the single-layer type photoreceptor using the ketone derivative (1), which is an electron transport agent, in combination with a hole transport agent excellent in hole transportability, includes the ketone derivative (1) and the hole transport agent. Therefore, even if both transport agents are contained in the same photosensitive layer at a high concentration, electron transport and hole transport can be performed efficiently, and a more sensitive photoreceptor is obtained. be able to. In addition, the single-layer type photoreceptor containing an electron acceptor together with the ketone derivative (1) can further improve the electron transport performance, and a more sensitive photoreceptor can be obtained.
[0038]
On the other hand, a multilayer photoreceptor is constituted by laminating a charge generation layer containing a charge generation agent and a charge transport layer containing a charge transfer agent in this order or in the reverse order on a support substrate. In addition, a photoconductive layer containing a charge transporting agent together with a charge generating agent may be combined with a charge transporting layer and a charge generating layer. The ketone derivative (1) can be contained in the charge transport layer or the photoconductive layer. However, since the charge generation layer has an extremely thin film pressure as compared with the charge transport layer, a charge generation layer is formed on a supporting substrate for protection, and a charge transport layer or a photoconductive layer is formed thereon. Is preferred.
[0039]
Depending on the order of formation of the charge generation layer and the charge transport layer and the type of the charge transport agent used in the charge transport layer, the stacked type photoreceptor is selected as a positive or negative charge type. For example, when an electron transport agent such as a ketone derivative (1) is used as a charge transport agent in a charge transport layer in a layer structure in which a charge generation layer is formed on a support substrate and a charge transport layer is formed thereon. Becomes a positively charged photoreceptor. In this case, the charge generation layer may contain a hole transport agent or an electron transport agent. Here, when an electron acceptor is contained in the charge transporting layer, the electron transporting property is improved, so that a laminated photoconductor with higher sensitivity can be obtained.
[0040]
In the above layer structure, when a hole transporting agent is used as the charge transporting agent in the charge transporting layer, a negatively charged photoreceptor is obtained. In this case, the charge generation layer may contain a ketone derivative (1) or an electron acceptor.
[0041]
The laminated photoreceptor described above has the advantages that the functions such as charge generation and charge transport are separated in each layer, so that the constituent materials are not wasted and the sensitivity is easily improved.
(Support base)
As the support substrate on which the photosensitive layer is formed, various materials having conductivity can be used. For example, iron, aluminum, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel Simple metal such as palladium, indium, stainless steel, brass, resin material on which the metal is vapor-deposited or laminated, resin material in which conductive filler such as carbon powder is dispersed, conductive polymer material, aluminum iodide, Examples thereof include glass coated with tin oxide, indium oxide and the like.
[0042]
The shape of the support substrate may be any of a sheet shape, a belt shape, a drum shape, or the like in accordance with the structure of the image forming apparatus to be used. The substrate itself is conductive or the surface of the substrate is conductive. As long as it has. Further, it is preferable that the support substrate has sufficient mechanical strength when used.
(Formation of photosensitive layer)
The photosensitive layer is formed by various conventionally known vapor deposition methods such as chemical vapor deposition methods such as plasma CVD method and photo CVD method, physical vapor deposition methods such as sputtering method, vacuum vapor deposition method and ion plating method, or coating methods. Can be formed.
[0043]
Of these, the coating method may be formed as follows.
[0044]
In the single-layer type photosensitive layer, the charge generating agent is preferably contained in a proportion of 0.1 to 50 parts by weight, particularly 0.5 to 30 parts by weight, with respect to 100 parts by weight of the binder resin. The ketone derivative (1) (electron transport agent) is preferably contained in an amount of 5 to 100 parts by weight, particularly 10 to 80 parts by weight, based on 100 parts by weight of the binder resin. Moreover, when it contains a hole transport agent, it is preferable to make it contain in the ratio of 5-500 weight part, especially 25-200 weight part, respectively. When the electron acceptor is contained, the proportion of the electron acceptor is preferably 0.1 to 40 parts by weight, particularly 0.5 to 20 parts by weight with respect to 100 parts by weight of the binder resin. Moreover, when using an electron transport agent and a hole transport agent together, the total amount is 20-500 weight part with respect to 100 weight part of binder resin, Especially 30-200 weight part is preferable.
[0045]
The thickness of the single-layer type photosensitive layer is preferably 5 to 100 μm, particularly preferably about 10 to 50 μm.
[0046]
In the charge generation layer of the multilayer photosensitive layer, the charge generation agent is preferably contained in an amount of 5 to 1000 parts by weight, particularly 30 to 500 parts by weight, with respect to 100 parts by weight of the binder resin. In the case where the charge generation layer contains a charge transport agent to form a photoconductive layer, when the ketone derivative (1) is contained with respect to 100 parts by weight of the binder resin, 1 to 200 parts by weight, particularly 5 to It is preferable to make it contain in the ratio of 100 weight part. When the hole transport agent is contained, the hole transport agent is preferably contained in an amount of 1 to 500 parts by weight, particularly 25 to 200 parts by weight. Moreover, when it contains an electron acceptor, it is preferable to make it contain in the ratio of 1-200 weight part, especially 5-100 weight part. When the electron acceptor and the hole transport agent are used in combination, the total amount is preferably 10 to 500 parts by weight, particularly 30 to 200 parts by weight, based on 100 parts by weight of the binder resin.
[0047]
In the charge transport layer, the ketone derivative (1) is contained in a proportion of 5 to 200 parts by weight, particularly 10 to 80 parts by weight, when the hole transport agent is contained with respect to 100 parts by weight of the binder resin. In the case of 10 to 500 parts by weight, particularly 25 to 100 parts by weight, when the electron acceptor is contained, the electron transport agent is contained in an amount of 0.1 to 250 parts by weight, particularly 1 to 150 parts by weight. Is preferred. When the electron acceptor and the hole transport agent are used in combination, the total amount is preferably 10 to 500 parts by weight, particularly 30 to 200 parts by weight, based on 100 parts by weight of the binder resin.
[0048]
The thickness of the laminated photosensitive layer is preferably 0.01 to 5 μm, particularly about 0.1 to 3 μm for the charge generation layer, and 2 to 100 μm, particularly about 5 to 50 μm for the charge transport layer.
[0049]
In a single layer type photoreceptor, between a support substrate and a photosensitive layer, and in a laminated type photoreceptor, between a support substrate and a charge generation layer, between a support substrate and a charge transport layer, or a charge generation layer, A barrier layer may be formed between the charge transport layer and the charge transport layer as long as the characteristics of the photoreceptor are not impaired. Further, a protective layer may be formed on the surface of the photoreceptor.
[0050]
When each layer constituting the photoreceptor is formed by a coating method, the charge generator, charge transport agent, binder resin and the like exemplified above, together with the organic solvent such as tetrahydrofuran described above, a known method, for example, A coating solution may be prepared by dispersing and mixing using a roll mill, ball mill, attritor, paint shaker or ultrasonic disperser, and this may be applied and dried by known means.
[0051]
Examples of the organic solvent for preparing the coating liquid include alcohols such as methanol, ethanol, isopropanol and butanol, aliphatic hydrocarbons such as n-hexane, octane and cyclohexane, and aromatic carbonization such as benzene, toluene and xylene. Halogenated hydrocarbons such as hydrogen, dichloromethane, dichloroethane, carbon tetrachloride, chlorobenzene, ethers such as dimethyl ether, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,3-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, acetone, Examples include ketones such as methyl ethyl ketone and cyclohexanone, esters such as ethyl acetate and methyl acetate, dimethylformaldehyde, dimethylformamide, and dimethyl sulfoxide. . These solvents are used alone or in admixture of two or more.
[0052]
Furthermore, in order to improve the dispersibility of the charge transport agent or charge generator and the smoothness of the surface of the photosensitive layer, a surfactant, a leveling agent or the like may be added to the coating solution.
(Image forming device)
FIG. 1 schematically shows an example of an image forming apparatus implemented in the present invention.
[0053]
Further, the image forming apparatus of the present invention is provided with a fixing
[0054]
When forming an image, the surface of the
[0055]
Thereafter, the developing means 4 develops the toner by attaching it to the portion corresponding to the electrostatic latent image. Then, the toner image on the surface of the
[0056]
After the transfer, the toner that cannot be transferred onto the transfer medium 8 and remains on the surface of the
[0057]
As the charging means 2, for example, a conventionally known method of applying corona discharge by applying a high voltage to a charge wire provided close to the surface of the
[0058]
The main charging voltage applied from the charging unit 2 to the
[0059]
As the exposure means 3, a laser beam having a wavelength at which the
[0060]
The exposure amount should be set so that the light potential is as low as possible. Specifically, the exposure is performed so that the light potential of the
[0061]
As the developing means 4, a conventionally known contact or non-contact developing apparatus can be used, and any of dry and wet methods can be used. The developer used for the developing means 4 may be either a one-component system or a two-component system.
[0062]
As the transfer means 5, any conventionally known contact transfer or non-contact transfer method can be applied. Specifically, a transfer voltage is applied to the
[0063]
As the separating means 6, as with the charging means 2, those using a corona discharge with a charge wire, those using a conductive roller, etc. can be used, and those using a corona discharge are preferably used. The separation voltage applied to the
[0064]
In the case where the static elimination means 7 is provided, a conventionally known static elimination lamp such as an LED array or a fluorescent tube can be used. As the charge eliminating lamp, a lamp that emits a sufficient amount of light to remove residual charges on the surface of the
[0065]
In the case where the cleaning means 9 is provided, a conventionally known mechanism such as a blade method, a fur brush method, a roller cleaning method, or the like can be used with a simple mechanism and good toner removal efficiency.
[0066]
As the fixing means 12, conventionally known methods such as heat fixing, pressure fixing, heat pressure fixing, flash fixing, etc. may be used.
[0067]
【Example】
Hereinafter, the present invention will be described based on synthesis examples, examples, and comparative examples.
(Synthesis of ketone derivative (1))
[Synthesis Example 1-1]
10 g (0.043 mol) of 3,5-di-t-butyl-4-hydroxybenzaldehyde and 8.79 g (0.043 mol) of R-(-)-2-phenylglycine hydrochloride were placed in a 300 ml flask, and 150 ml of pyridine was added. In addition, heating under reflux was performed for 3 hours. The reaction solution was cooled, poured into 300 ml of dilute hydrochloric acid aqueous solution, and the precipitated solid was separated by filtration. The solid was dissolved in 150 ml of chloroform, washed with water repeatedly, the organic layer was dried over anhydrous magnesium sulfate, and the organic layer was distilled off.
[0068]
The obtained red residue was again dissolved in 100 ml of chloroform, 20 g of silver oxide was added, and the mixture was stirred overnight at room temperature. Silver oxide is filtered off, and the organic layer is purified by silica gel column chromatography (chloroform development)
8.1 g (yield 49.6%) of the desired product (hereinafter referred to as ketone derivative (1-1)) was obtained.
The following general formula (1-1):
[0069]
[Chemical 6]
The infrared absorption spectrum of the above ketone derivative (1-1) is shown in FIG.
[Synthesis Example 1-2]
(Similar to Example 1-1, L-alanine methyl ester hydrochloride 6 g (0.043 mol) was used to obtain 5.5 g (yield) of the desired product (hereinafter referred to as ketone derivative (1-2)). 40%).
The following general formula (1-2):
[0071]
[Chemical 7]
FIG. 3 shows the infrared absorption spectrum of the above-mentioned ketone derivative (1-2).
[Synthesis Example 1-3]
5.6 g (hereinafter referred to as ketone derivative (1-3)) using 6.6 g (0.043 mol) of L-alanine ethyl ester hydrochloride as the starting material as in Example 1-1 Yield 39%).)
The following general formula (1-3):
[0073]
[Chemical 8]
The infrared absorption spectrum of the ketone derivative (1-3) is shown in FIG.
[Synthesis Example 1-4]
(In the same manner as in Example 1-1, 6.53 g (yield 42%) of the target product (hereinafter referred to as ketone derivative (1-4)) was obtained using 7.9 g (0.043 mol) of dimethylaminomalonate hydrochloride. )
The following general formula (1-4):
[0075]
[Chemical 9]
FIG. 5 shows the infrared absorption spectrum of the above-mentioned ketone derivative (1-4).
[Synthesis Example 1-5]
(As in Example 1-1, 6.8 g (yield: 40.6%) of the desired product (hereinafter referred to as ketone derivative (1-5)) was obtained using 9.1 g (0.043 mol) of dimethylaminomalonate hydrochloride. Obtained.)
The following general formula (1-5):
[0077]
[Chemical Formula 10]
FIG. 6 shows the infrared absorption spectrum of the above-mentioned ketone derivative (1-5).
(Production of single layer type electrophotographic photoreceptor)
[Example 1-1]
5 parts by weight of X-type metal-free phthalocyanine as a charge generator, 100 parts by weight of polycarbonate as a binder resin, 800 parts by weight of tetrahydrofuran as a solvent, N, N, N ′, N′-tetrakis (3-methylphenyl) as a hole transport agent ) 50 parts by weight of 3,3′-diaminobenzidine and 30 parts by weight of a ketone derivative (1-1) as an electron transporting agent were mixed and dispersed in a ball mill for 50 hours to prepare a coating solution for a single-layer photoreceptor. . Next, this coating solution was applied onto an aluminum sheet using a wire bar and dried at 100 ° C. for 1 hour to form a photosensitive layer having a thickness of 20 μm, thereby producing a single-layer type photoreceptor.
[Example 1-2]
A single layer type photoreceptor was produced in the same manner as in Example 1-1 except that the ketone derivative (1-2) was used instead of the ketone derivative (1-1).
[Example 1-3]
A monolayer type photoreceptor was produced in the same manner as in Example 1-1 except that the ketone derivative (1-3) was used instead of the ketone derivative (1-1).
[Example 1-4]
A monolayer type photoreceptor was produced in the same manner as in Example 1-1 except that the ketone derivative (1-4) was used in place of the ketone derivative (1-1).
[Example 1-5]
A monolayer type photoreceptor was produced in the same manner as in Example 1-1 except that the ketone derivative (1-5) was used instead of the ketone derivative (1-1).
[Example 1-6]
A single layer type photoreceptor was produced in the same manner as in Example 1-1 except that the ketone derivative (1-6) was used instead of the ketone derivative (1-1).
[Comparative Example 1-1]
Instead of the ketone derivative (1-1), the general formula (C1-1):
[0079]
Embedded image
(T-Bu represents a t-butyl group.)
A single-layer photoreceptor was produced in the same manner as in Example 1-1 except that the compound represented by
[Comparative Example 1-2]
Instead of the ketone derivative (1-1), the general formula (C2-1):
[0081]
Embedded image
A single-layer photoreceptor was produced in the same manner as in Example 1-1 except that the compound represented by
(Evaluation of photoconductor)
The electrophotographic photosensitive member is installed in an electrostatic copying apparatus (in the case of a single-layer photosensitive member, Kyocera Mita KM-4530 is used), and the surface potential is +700 V in the case of a single-layer photosensitive member. In the case of a multilayer photoreceptor, charging was performed while setting a grid voltage to be −700V. Next, the surface potential was measured under the same conditions as the grid voltage set before exposure by exposing to an ozone atmosphere (5 ppm) for 5 hours.
[0083]
Furthermore, the amount of change in surface potential (V) before and after exposure to ozone was determined to evaluate the ozone resistance of the electrophotographic photoreceptor. For example, if the surface potential before exposure to ozone is + 850V and the surface potential after exposure is + 740V, the evaluation is -110V. The amount of change in surface potential before and after exposure to ozone should be within ± 100V, preferably within ± 60V for single-layer type photoreceptors using X-type metal-free phthalocyanine (the amount of decrease or increase in surface potential after exposure is It may be smaller than the absolute value of the above value). It can be said that the greater the amount of change, the lower the ozone resistance of the electrophotographic photoreceptor. The results of the single layer type photoreceptor are shown in Table 1.
[0084]
[Table 1]
From Table 1, the single layer type photoreceptors of Examples 1-1, 1-3, and 1-5 are compared with the single layer type photoreceptors of Comparative Examples 1-1 and 1-2, and the surface before and after exposure to ozone. It was confirmed that the amount of potential change was small.
(Image evaluation)
The photoconductors obtained in Examples and Comparative Examples were mounted on an electrostatic copying machine (KM-4530 manufactured by Kyocera Mita Co., Ltd.) was installed, and after initial setting, a single copy was performed 1000 times. Thereafter, an image was output, and the image fog of the blank paper portion and the image density of the solid black portion were visually confirmed. The electrostatic copying machine has the following settings.
・ Charging: Scorotron (initial surface potential approx. 700V)
・ Exposure: Laser light
・ Development: Reverse development
・ Transcription: Transcription charger
・ Cleaning: Cleaning blade method
-Static elimination: Static elimination lamp (LED)
・ Separation: Charge wire
・ Fixing: Thermal pressure fixing
As a result, when the single-layer type photoreceptors obtained in Examples 1-1 to 1-6 were used, an image having a sufficient density with no image fogging and no blurring even in a solid black portion was obtained. On the other hand, when the single layer type photoconductors of Comparative Examples 1-1 and 1-2 were used, image fogging occurred and solid black portions were blurred and an image having a sufficient density could not be obtained.
[0086]
【The invention's effect】
As described above, since the electrophotographic photosensitive member of the present invention contains the ketone derivative (1), it is excellent in gas resistance and does not deteriorate in electrical characteristics even when used for a long time.
[0087]
In addition, since the image forming apparatus of the present invention uses the electrophotographic photosensitive member, a good image having high image density and no image fog can be obtained even when image formation is repeated.
[Brief description of the drawings]
FIG. 1 is a diagram showing an image forming apparatus of the present invention.
FIG. 2 is an infrared absorption spectrum of a ketone derivative (1-1).
FIG. 3 is an infrared absorption spectrum of a ketone derivative (1-2).
FIG. 4 is an infrared absorption spectrum of a ketone derivative (1-4).
Claims (2)
で表されるケトン誘導体を含有することを特徴とする電子写真感光体。An electrophotographic photosensitive member having a photosensitive layer provided on a supporting substrate, wherein the photosensitive layer has the general formula (1):
An electrophotographic photoreceptor comprising a ketone derivative represented by the formula:
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