JP3286711B2 - Electrophotographic photoreceptor - Google Patents
Electrophotographic photoreceptorInfo
- Publication number
- JP3286711B2 JP3286711B2 JP06906691A JP6906691A JP3286711B2 JP 3286711 B2 JP3286711 B2 JP 3286711B2 JP 06906691 A JP06906691 A JP 06906691A JP 6906691 A JP6906691 A JP 6906691A JP 3286711 B2 JP3286711 B2 JP 3286711B2
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- Japan
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- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Description
【０００１】[0001]
【産業上の利用分野】本発明は表面保護層を有する電子
写真用感光体に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photosensitive member having a surface protective layer.
【０００２】[0002]
【従来の技術】従来、電子写真感光体としては、導電性
支持体上にセレンないしセレン合金を主体とする光導電
層を設けたもの、酸化亜鉛、酸化カドミウムなどの無機
光導電材料をバインダー中に分散させたもの、ポリ−Ｎ
−ビニルカルバゾールとトリニトロフルオレノンあるい
はアゾ顔料などの有機光導電材料を用いたもの及び非晶
質シリコンを用いたもの等が一般に知られている。これ
らの感光体に対して、長時間高画質を保つ信頼性の要求
が年々高まっている。しかし光導電層が露出している場
合、帯電過程のコロナ放電による損傷と複写プロセスで
受ける他部材との接触による物理的あるいは化学的な損
傷が感光体の寿命を損なうものであった。2. Description of the Related Art Conventionally, an electrophotographic photoreceptor has a photoconductive layer mainly composed of selenium or a selenium alloy provided on a conductive support, and an inorganic photoconductive material such as zinc oxide or cadmium oxide is used in a binder. Poly-N
-Those using an organic photoconductive material such as vinyl carbazole and trinitrofluorenone or azo pigment, those using amorphous silicon, and the like are generally known. The demand for reliability for maintaining high image quality for a long time for these photoconductors is increasing year by year. However, when the photoconductive layer is exposed, the damage caused by corona discharge during the charging process and the physical or chemical damage caused by contact with other members during the copying process impair the life of the photoconductor.
【０００３】このような欠点を解消する方法として感光
体表面に保護層を設ける技術が知られている。具体的に
は感光層の表面に有機フィルムを設ける方法（特公昭３
８−１５４４６）、無機酸化物を設ける方法（特公昭４
３−１４５１７）、接着層を設けた後、絶縁層を積層す
る方法（特公昭４３−２７５９１）、あるいはプラズマ
ＣＶＤ法・光ＣＶＤ法等によってａ−Ｓｉ層、ａ−Ｓ
ｉ：Ｎ：Ｈ層、ａ−Ｓｉ：Ｏ：Ｈ層等を積層する方法
（特開昭５７−１７９８５９、特開昭５９−５８４３
７）が開示されている。しかしながら、保護層が電子写
真的に高抵抗（１０14Ω・ｃｍ以上）になると、残留電
位の増大、繰返時の蓄積などが問題となり、実用上好ま
しくない。As a method for solving such a defect, a technique of providing a protective layer on the surface of a photoreceptor is known. Specifically, a method of providing an organic film on the surface of the photosensitive layer (Japanese Patent Publication No.
8-15446), a method of providing an inorganic oxide (Japanese Patent Publication No. Sho 4
3-14517), an a-Si layer, an a-S layer by a method of laminating an insulating layer after providing an adhesive layer (Japanese Patent Publication No. 43-27591), a plasma CVD method, an optical CVD method, or the like.
A method of laminating an i: N: H layer, an a-Si: O: H layer, etc. (Japanese Patent Application Laid-Open Nos. 57-17959 and 59-5843)
7) is disclosed. However, if the protective layer becomes electrophotographically high in resistance (10 14 Ω · cm or more), problems such as an increase in residual potential and accumulation during repetition become unfavorable in practical use.
【０００４】上記欠点を補う技術として保護層を光導電
層とする方法（特公昭４８−３８４２７、特公昭４３−
１６１９８、特公昭４９−１０２５８、ＵＳＰ−２９０
１３４８）、保護層中に色素やルイス酸に代表される移
動剤を添加する方法（特公昭４４−８３４、特開昭５３
−１３３４４４）、或いは金属や金属酸化物微粒子の添
加により保護層の抵抗を制御する方法（特開昭５３−３
３３８）等が提案されている。しかし、このような場合
には保護層による光の吸収が生じ光導電層へ到達する光
量が減少するため、結果として電子写真用感光体の感度
が低下するという問題が生じる。As a technique for compensating the above-mentioned drawbacks, a method in which a protective layer is used as a photoconductive layer (Japanese Patent Publication No. 48-38427, Japanese Patent Publication No.
16198, JP-B-49-10258, USP-290
1348), a method of adding a dye or a transfer agent typified by a Lewis acid to the protective layer (Japanese Patent Publication No. 44-834, Japanese Patent Publication No.
-133444) or a method of controlling the resistance of the protective layer by adding fine particles of metal or metal oxide (JP-A-53-3).
338) has been proposed. However, in such a case, light is absorbed by the protective layer, and the amount of light reaching the photoconductive layer is reduced. As a result, there is a problem that the sensitivity of the electrophotographic photosensitive member is reduced.
【０００５】この様な観点から特開昭５７−３０８４６
に開示されているように平均粒径０．３μｍ以下の金属
酸化物微粒子を抵抗制御剤として表面保護層中に分散さ
せることにより、可視光に対して実質的に透明にする方
法がある。この表面保護層をもった電子写真用感光体は
感度低下も少なく、表面保護層の機械的強度も増し、耐
久性が向上する。しかしながら、この感光体を実際の複
写機に組み込んだ場合、残留電位が生じ画像上に地肌汚
れを発生させるという欠点がある。この残留電位は表面
保護層上に蓄積した残留電荷により発生し、特に低温低
湿時に著しく増大する。[0005] From such a viewpoint, Japanese Patent Application Laid-Open No. 57-30846.
There is a method of dispersing metal oxide fine particles having an average particle diameter of 0.3 μm or less in a surface protective layer as a resistance control agent to make them substantially transparent to visible light as disclosed in US Pat. The electrophotographic photoreceptor having the surface protective layer has little decrease in sensitivity, increases the mechanical strength of the surface protective layer, and improves durability. However, when this photoreceptor is incorporated in an actual copying machine, there is a drawback that a residual potential is generated and a background stain is generated on an image. This residual potential is generated by residual charges accumulated on the surface protective layer, and particularly increases remarkably at low temperature and low humidity.
【０００６】[0006]
【発明が解決しようとする課題】本発明はこうした実情
に鑑み、高い機械的強度を備えかつ低湿時に残留電位の
増加を生じない安定な電気特性を示す保護層を有し、長
期に渡って品質の高い画像を安定して形成しうる電子写
真用感光体を提供することを目的とする。SUMMARY OF THE INVENTION In view of the above circumstances, the present invention has a protective layer having high mechanical strength and exhibiting stable electric characteristics which does not cause an increase in residual potential at low humidity, and has a long-lasting quality. It is an object of the present invention to provide an electrophotographic photoreceptor capable of stably forming an image having high image quality.
【０００７】[0007]
【課題を解決するための手段】本発明は、以下の発明が
提供される。 （１）導電性支持体上に光導電層及び表面保護層を順次
積層した電子写真用感光体において、該表面保護層が結
着樹脂中に正孔搬送物質として一般式（１）乃至（７）
で示される化合物を少なくとも１つを含有し、且つ表面
保護層の全重量の４３重量％以上６０重量％以下の導電
性を有する金属酸化物の微粉末を含有させたことを特徴
とする電子写真用感光体。Means for Solving the Problems The present invention provides the following inventions. (1) In an electrophotographic photoreceptor in which a photoconductive layer and a surface protective layer are sequentially laminated on a conductive support, the surface protective layer is represented by a general formula (1) to (7 ) as a hole transport material in a binder resin. )
Wherein at least one compound represented by the formula (1) is contained, and fine powder of conductive metal oxide is contained in an amount of 43 to 60% by weight based on the total weight of the surface protective layer. Photoreceptor.
【０００８】[0008]
【化１０】 〔式中、Ａ1，Ａ2は置換もしくは無置換のアルキル基又
は置換もしくは無置換のアリール基を表わし、それぞれ
同一でも異なっていてもよく、Ａｒは置換又は無置換の
縮合多環式炭化水素基を表わす〕Embedded image [In the formula, A 1 and A 2 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, which may be the same or different, and Ar is a substituted or unsubstituted fused polycyclic hydrocarbon. Represents a group)
【０００９】[0009]
【化１１】 〔式中、Ｒはカルバゾリル基、ピリジル基、チエニル
基、インドリル基、フリル基あるいはそれぞれ置換もし
くは無置換のフェニル基、スチリル基、ナフチル基又は
アントリル基を表わし、該置換基はジアルキルアミノ
基、アルキル基、アルコキシ基、カルボキシ基もしくは
そのエステル基、ハロゲン原子、シアノ基、アラルキル
アミノ基、Ｎ−アルキル−Ｎ−アラルキルアミノ基、ア
ミノ基、ニトロ基およびアセチルアミノ基からなる群か
ら選ばれた基を表わす〕Embedded image [In the formula, R represents a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, a furyl group or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group or an anthryl group, and the substituent is a dialkylamino group, an alkyl group A group selected from the group consisting of a group, an alkoxy group, a carboxy group or an ester group thereof, a halogen atom, a cyano group, an aralkylamino group, an N-alkyl-N-aralkylamino group, an amino group, a nitro group and an acetylamino group. Express)
【００１０】[0010]
【化１２】 〔式中、ｎは０又は１の整数、Ｒ1は水素原子、アルキ
ル基又は置換もしくは無置換のフェニル基を表し、ＡはEmbedded image [In the formula, n represents an integer of 0 or 1, R 1 represents a hydrogen atom, an alkyl group or a substituted or unsubstituted phenyl group;
【化１３】 ９−アントリル基又は置換もしくは無置換のＮ−アルキ
ルカルバゾリル基を表わし、ここでＲ2は水素原子、ア
ルキル基、アルコキシ基、ハロゲン原子又はEmbedded image Represents a 9-anthryl group or a substituted or unsubstituted N-alkylcarbazolyl group, wherein R 2 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or
【化１４】 （但し、Ｒ3およびＲ4はアルキル基、置換もしくは無置
換のアラルキル基、置換もしくは無置換のアリール基を
示し、Ｒ3およびＲ4は環を形成してもよい）を表わし、
ｍは０，１，２又は３の整数であって、ｍが２以上のと
きはＲ2は同一でも異なってもよい〕Embedded image Wherein R 3 and R 4 represent an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, and R 3 and R 4 may form a ring.
m is an integer of 0, 1, 2, or 3, and when m is 2 or more, R 2 may be the same or different.
【００１１】[0011]
【化１５】 〔式中、Ｒ1は低級アルキル基又はベンジル基を表わ
し、Ｒ2は水素原子、低級アルキル基、低級アルコキシ
基、ハロゲン原子、ニトロ基、アミノ基又は低級アルキ
ル基もしくはベンジル基で置換されたアミノ基を表わ
し、ｎは１又は２の整数を表わす〕Embedded image Wherein R 1 represents a lower alkyl group or a benzyl group; R 2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group or an amino group substituted with a lower alkyl group or a benzyl group; And n represents an integer of 1 or 2.
【００１２】[0012]
【化１６】 〔式中、Ｒ1は水素原子、アルキル基、アルコキシ基又
はハロゲン原子を表わし、Ｒ2およびＲ3はアルキル基、
置換もしくは無置換のアラルキル基又は置換もしくは無
置換のアリール基を表わし、Ｒ4は水素原子又は置換も
しくは無置換のフェニル基を表わし、また、Ａｒはフェ
ニル基又はナフチル基を表わす〕Embedded image [In the formula, R 1 represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, and R 2 and R 3 represent an alkyl group,
Represents a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group, R 4 represents a hydrogen atom or a substituted or unsubstituted phenyl group, and Ar represents a phenyl group or a naphthyl group]
【００１３】[0013]
【化１７】 〔式中、Ｒは水素又はハロゲン原子を表わし、Ａｒは置
換もしくは無置換のフェニル基、ナフチル基、アントリ
ル基又はカルバゾリル基を表わす〕Embedded image [Wherein, R represents hydrogen or a halogen atom, and Ar represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group or carbazolyl group]
【００１４】[0014]
【化１８】 〔式中、Ｒ1，Ｒ2およびＲ3は水素、低級アルキル基、
低級アルコキシ基、ジアルキルアミノ基又はハロゲン原
子を表わし、ｎは０又は１を表わす〕Embedded image Wherein R 1 , R 2 and R 3 are hydrogen, a lower alkyl group,
Represents a lower alkoxy group, a dialkylamino group or a halogen atom, and n represents 0 or 1]
【００１５】[0015]
【発明の実施の形態】以下、本発明をさらに詳しく説明
する。本発明に用いられる正孔搬送物質としては次のよ
うなものが挙げられる。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail. The hole transporting substances used in the present invention include the following.
【００１６】一般式（１）で表わされる化合物の具体例
としては、１−Ｎ，Ｎ−ビス（４−メチルフェニル）ア
ミノピレン、１−Ｎ，Ｎ−ビス（３−メチルフェニル）
アミノピレンなどがある。Specific examples of the compound represented by the general formula (1) include 1-N, N-bis (4-methylphenyl) aminopyrene, 1-N, N-bis (3-methylphenyl)
And aminopyrene.
【００１７】一般式（２）で表わされる化合物の具体例
としては、１，２−ビス（４−ジエチルアミノスチリ
ル）ベンゼン、１，２−ビス（２，４−ジメトキシスチ
リル）ベンゼンがある。 Specific examples of the compound represented by the general formula (2)
As 1,2-bis (4-diethylaminostyryl)
B) benzene, 1,2-bis (2,4-dimethoxysty)
Lil) There is benzene.
【００１８】一般式（３）で表わされる化合物の具体例
としては、４’−ジフェニルアミノ−α−フェニルスチ
ルベン、４’−メチルフェニルアミノ−α−フェニルス
チルベンなどがある。Specific examples of the compound represented by the general formula (3) include 4'-diphenylamino-α-phenylstilbene and 4'-methylphenylamino-α-phenylstilbene.
【００１９】一般式（４）で表わされる化合物の具体例
としては、３−スチリル−９−エチルカルバゾール、３
−（４−メトキシスチリル）−９−エチルカルバゾール
などがある。Specific examples of the compound represented by the general formula (4) include 3-styryl-9-ethylcarbazole,
-(4-methoxystyryl) -9-ethylcarbazole and the like.
【００２０】一般式（５）で表わされる化合物の具体例
としては、４−ジフェニルアミノスチルベン、４−ジベ
ンジルアミノスチルベン、４−ジトリルアミノスチルベ
ン、１−（４−ジフェニルアミノスチリル）ナフタレ
ン、１−（４−ジエチルアミノスチリル）ナフタレンな
どがある。Specific examples of the compound represented by formula (5) include 4-diphenylaminostilbene, 4-dibenzylaminostilbene, 4-ditolylaminostilbene, 1- (4-diphenylaminostyryl) naphthalene, -(4-diethylaminostyryl) naphthalene and the like.
【００２１】一般式（６）で表わされる化合物の具体例
としては、９−（４−ジエチルアミノスチリル）アント
ラセン、９−ブロム−１０−（４−ジエチルアミノスチ
リル）アントラセンなどがある。Specific examples of the compound represented by the general formula (6) include 9- (4-diethylaminostyryl) anthracene and 9-bromo-10- (4-diethylaminostyryl) anthracene.
【００２２】一般式（７）で表わされる化合物の具体例
としては、１−フェニル−３−（４−ジエチルアミノス
チリル）−５−（４−ジエチルアミノフェニル）ピラゾ
リン、１−フェニル−３−（４−ジメチルアミノスチリ
ル）−５−（４−ジメチルアミノフェニル）ピラゾリン
などがある。Specific examples of the compound represented by the general formula (7) include 1-phenyl-3- (4-diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazoline and 1-phenyl-3- (4- Dimethylaminostyryl) -5- (4-dimethylaminophenyl) pyrazolin.
【００２３】これらの化合物は単独でも２種以上併用し
ても良い。正孔搬送物質と結着樹脂との重量比は１：９
９〜５０：５０であり、好ましくは１０：９０〜２０：
８０である。１：９９未満では残留電位低減の効果は無
く、５０：５０超では機械的強度が劣化する。本発明の
表面保護層を形成するには、導電性を有する金属又は金
属酸化物の微粉末を結着樹脂溶液中にボールミルあるい
はビーズミルなどの方法で分散し、次にこの分散液にた
いし正孔搬送物質と結着樹脂との重量比が１：９９〜５
０：５０になるように上記正孔搬送物質を添加し、これ
を光導電層上に浸漬・スプレーなどの方法で塗布、乾燥
し、硬化させればよい。These compounds may be used alone or in combination of two or more. The weight ratio of the hole transport material to the binder resin is 1: 9.
9:50:50, preferably 10: 90-20:
80. If it is less than 1:99, there is no effect of reducing the residual potential, and if it exceeds 50:50, the mechanical strength is deteriorated. In order to form the surface protective layer of the present invention, fine powder of a conductive metal or metal oxide is dispersed in a binder resin solution by a method such as a ball mill or a bead mill. The weight ratio of the hole transport material to the binder resin is 1:99 to 5
The above-described hole transporting substance may be added so that the ratio becomes 0:50, and this may be applied onto the photoconductive layer by a method such as immersion or spraying, dried and cured.
【００２４】本発明に用いられる導電性を有する金属酸
化物の微粉末としては、酸化スズ、酸化亜鉛、酸化チタ
ン、酸化インジウム、アンチモンをドープした酸化ス
ズ、スズをドープした酸化インジウム等の金属酸化物の
微粉末を用いることができる。これら金属あるいは金属
酸化物の微粉末は２種以上混合してもかまわない。これ
ら微粉末の平均粒径は０．５μｍ以下、好ましくは０．
２μｍ以下にあることが保護層の光透過率の点から好ま
しい。The fine powder of a conductive metal oxide used in the present invention includes tin oxide, zinc oxide, titanium oxide, indium oxide, tin oxide doped with antimony, and tin-doped indium oxide. Fine powder can be used. Two or more of these metal or metal oxide fine powders may be mixed. The average particle size of these fine powders is 0.5 μm or less, preferably 0.1 μm.
It is preferably from 2 μm or less from the viewpoint of the light transmittance of the protective layer.
【００２５】本発明に用いられる結着樹脂としては、シ
リコーン樹脂、ポリウレタン樹脂、アクリル樹脂、ポリ
エステル樹脂、ポリカーボネート樹脂、ポリスチレン樹
脂、エポキシ樹脂等が例示できる。なお、保護層中には
分散性、接着性あるいは平滑性を向上させる目的で種々
の添加剤を加えても良い。Examples of the binder resin used in the present invention include silicone resin, polyurethane resin, acrylic resin, polyester resin, polycarbonate resin, polystyrene resin, epoxy resin and the like. Various additives may be added to the protective layer for the purpose of improving dispersibility, adhesiveness, or smoothness.
【００２６】本発明に用いられる光導電層としては、Ｓ
ｅ、Ｓｅ−Ｔｅ、Ａｓ2Ｓｅ3等のＳｅ合金、ＺｎＯ、Ｃ
ｄＳ、ＣｄＳｅ等のII〜VI族化合物の粒子を樹脂に分散
させたもの、ポリビニルカルバゾール等の有機光導電材
料あるいはａ−Ｓｉ等が用いられる。光導電層の構成は
特に制約がなく、単層でも電荷発生層と電荷輸送層の積
層であってもかまわない。さらに保護層と光導電層との
間に密着性を高めるための接着層や電荷注入を阻止する
ための電気的バリアー層を設けてもよい。As the photoconductive layer used in the present invention, S
e, Se-Te, Se alloys such as As 2 Se 3, ZnO, C
A dispersion of particles of a group II-VI compound such as dS and CdSe in a resin, an organic photoconductive material such as polyvinyl carbazole, or a-Si is used. The configuration of the photoconductive layer is not particularly limited, and may be a single layer or a laminate of the charge generation layer and the charge transport layer. Further, between the protective layer and the photoconductive layer, an adhesive layer for improving the adhesion and an electric barrier layer for preventing charge injection may be provided.
【００２７】導電性支持体としては、導電体あるいは、
導電処理をした絶縁体が用いられる。たとえばＡｌ、Ｎ
ｉ、Ｆｅ、Ｃｕ、Ａｕなどの金属あるいは合金、ポリエ
ステル、ポリカーボネート、ポリイミド、ガラス等の絶
縁性基体上にＡｌ、Ａｇ、Ａｕ等の金属あるいはＩｎ2
Ｏ3、ＳｎＯ2等の導電材料の薄膜を形成したもの、導電
処理をした紙等が例示できる。また導電性支持体の形状
は特に制約はなく、必要に応じて板状、ドラム状、ベル
ト状のものが用いられる。As the conductive support, a conductor or
An insulator subjected to a conductive treatment is used. For example, Al, N
i, Fe, Cu, Au or other metal or alloy, polyester, polycarbonate, polyimide, glass or other insulating substrate on a metal such as Al, Ag, Au or In 2
Examples thereof include those in which a thin film of a conductive material such as O 3 and SnO 2 is formed, and paper subjected to a conductive treatment. The shape of the conductive support is not particularly limited, and a plate, a drum, or a belt may be used as needed.
【００２８】[0028]
【実施例】以下、本発明を実施例に従って説明する。 参考例１ ８０ｍｍφ×３４０ｍｍ（長さ）のＡｌドラム支持体を
真空蒸着装置内にセットし、またこの装置の蒸着源ボー
トにＡｓ2Ｓｅ3合金を入れ、真空度３／１０6Ｔｏｒ
ｒ、支持体温度２００℃、ボート温度４５０℃の条件で
蒸着を行い、支持体上に６０μｍ厚の光導電層を形成し
た。次にこの上に、ａ）アルコキシ基含有ポリシロキサ
ンとｂ）水酸基含有ポリシロキサンとｃ）炭素原子に結
合したアミノ基、イミノ基又はニトリル基を少なくとも
１個及びアルコキシ基が２〜３個結合した珪素原子を有
する有機珪素化合物とを主成分とするシリコーン樹脂Ａ
（トーレシリコーン社製ＡＹ４２−４４０）と前記
ａ）、ｂ）及びｃ）の成分比が異なるシリコーン樹脂Ｂ
（トーレシリコーン社製ＡＹ４２−４４１）との等量
（重量）混合物のリグロイン溶液をスプレー塗布し、１
２０℃で１時間乾燥して０．１５μｍ厚の電気的バリア
ー層（中間層）を形成した。次にＳｔ−ＭＭＡ−２−Ｈ
ＥＭＡ共重合体の２０ｗｔ％酢酸２−エトキシエチル／
メチルイソブチルケトン（７／３重量比）溶液３０重量
部と抵抗制御剤ＳｎＯ2１４重量部とをボールミルで１
２０時間分散後、ヘキサメチレンジイソシアナート３重
量部、４−メトキシベンズアルデヒド１−メチル−１−
フェニルヒドラゾン０．９重量部を加えこれを電気的バ
リアー層（中間層）上にスプレー塗布し、１３０℃で１
時間の乾燥を行い５μｍ厚の表面保護層（ＳｎＯ2含有
量：５８重量％）を形成し、電子写真用感光体を作製し
た。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below with reference to embodiments. REFERENCE EXAMPLE 1 An Al drum support of 80 mmφ × 340 mm (length) was set in a vacuum evaporation apparatus, and an As 2 Se 3 alloy was put in an evaporation source boat of this apparatus, and the degree of vacuum was 3/10 6 Torr.
r, evaporation was performed under the conditions of a support temperature of 200 ° C. and a boat temperature of 450 ° C. to form a 60 μm thick photoconductive layer on the support. Next, a) an alkoxy group-containing polysiloxane, b) a hydroxyl group-containing polysiloxane, and c) at least one amino group, imino group, or nitrile group bonded to a carbon atom, and two to three alkoxy groups. Silicone resin A containing an organosilicon compound having a silicon atom as a main component
(AY42-440 manufactured by Toray Silicone Co., Ltd.) and silicone resin B having different component ratios of the above a), b) and c)
(AY42-441 manufactured by Toray Silicone Co., Ltd.) was spray-coated with a ligroin solution of an equal amount (weight) of the mixture.
After drying at 20 ° C. for 1 hour, an electrical barrier layer (intermediate layer) having a thickness of 0.15 μm was formed. Next, St-MMA-2-H
20 wt% of EMA copolymer 2-ethoxyethyl acetate /
30 parts by weight of a methyl isobutyl ketone (7/3 weight ratio) solution and 14 parts by weight of a resistance control agent SnO 2
After 20 hours of dispersion, 3 parts by weight of hexamethylene diisocyanate, 4-methoxybenzaldehyde 1-methyl-1-
0.9 parts by weight of phenylhydrazone was added and spray-coated on the electrical barrier layer (intermediate layer).
After drying for a time, a surface protective layer (SnO 2 content: 58% by weight) having a thickness of 5 μm was formed, thereby producing an electrophotographic photoreceptor.
【００２９】参考例２ 前記正孔搬送物質を４−メトキシベンズアルデヒド１−
メチル−１−フェニルヒドラゾン０．０９重量部に変え
た他は参考例１と全く同様にして表面保護層（ＳｎＯ2
含有量：６０重量％）を有する電子写真用感光体を作製
した。Reference Example 2 The above-mentioned hole transporting substance was 4-methoxybenzaldehyde 1-
A surface protective layer (SnO 2 ) was prepared in exactly the same manner as in Reference Example 1 except that the amount was changed to 0.09 parts by weight of methyl-1-phenylhydrazone.
(Content: 60% by weight).
【００３０】参考例３ 前記正孔搬送物質を４−メトキシベンズアルデヒド１−
メチル−１−フェニルヒドラゾン９重量部に変えた他は
参考例１と全く同様にして表面保護層（ＳｎＯ2含有
量：４３％）を有する電子写真用感光体を作製した。Reference Example 3 The above-mentioned hole transporting substance was 4-methoxybenzaldehyde 1-
An electrophotographic photoreceptor having a surface protective layer (SnO 2 content: 43%) was prepared in exactly the same manner as in Reference Example 1 except that the amount of methyl-1-phenylhydrazone was changed to 9 parts by weight.
【００３１】参考例４ 前記正孔搬送物質を４−ジメトキシベンズアルデヒド１
−ベンジル−１−フェニルヒドラゾン０．９重量部に変
えた他は参考例１と全く同様にして電子写真用感光体を
作製した。Reference Example 4 The above-mentioned hole transporting substance was 4-dimethoxybenzaldehyde 1
A photoconductor for electrophotography was prepared in exactly the same manner as in Reference Example 1 except that 0.9 parts by weight of -benzyl-1-phenylhydrazone was used.
【００３２】参考例５ 前記正孔搬送物質を９−エチルカルバゾール−３−アル
デヒド１−メチル−１−フェニルヒドラゾン０．９重量
部に変えた他は参考例１と同様にして電子写真用感光体
を作製した。REFERENCE EXAMPLE 5 An electrophotographic photoreceptor was prepared in the same manner as in Reference Example 1 except that the hole transporting material was changed to 0.9 parts by weight of 9-ethylcarbazole-3-aldehyde 1-methyl-1-phenylhydrazone. Was prepared.
【００３３】参考例６ 前記正孔搬送物質を９−エチルカルバゾール−３−アル
デヒド１−メチル−１−フェニルヒドラゾン０．０９重
量部に変えた他は参考例１と全く同様にして電子写真感
光体を作製した。REFERENCE EXAMPLE 6 An electrophotographic photoreceptor was prepared in the same manner as in Reference Example 1, except that the hole transporting material was changed to 0.09 parts by weight of 9-ethylcarbazole-3-aldehyde 1-methyl-1-phenylhydrazone. Was prepared.
【００３４】参考例７ 前記正孔搬送物質を９−エチルカルバゾール−３−アル
デヒド１−メチル−１−フェニルヒドラゾン９重量部に
変えた他は参考例１と全く同様にして電子写真用感光体
を作製した。Reference Example 7 An electrophotographic photosensitive member was prepared in the same manner as in Reference Example 1, except that the hole transporting material was changed to 9 parts by weight of 9-ethylcarbazole-3-aldehyde 1-methyl-1-phenylhydrazone. Produced.
【００３５】参考例８ 前記正孔搬送物質を９−エチルカルバゾール−３−アル
デヒド１−ベンジル−１−フェニルヒドラゾン０．９重
量部に変えた他は参考例１と全く同様にして電子写真用
感光体を作製した。REFERENCE EXAMPLE 8 Electrophotographic exposure was carried out in exactly the same manner as in Reference Example 1, except that the hole-transporting substance was changed to 0.9 parts by weight of 9-ethylcarbazole-3-aldehyde 1-benzyl-1-phenylhydrazone. The body was made.
【００３６】参考例９ 前記搬送物質を４−メトキシナフタレン−１−アルデヒ
ド１−ベンジル−１−フェニルヒドラゾン０．９重量部
に変えた他は参考例１と全く同様にして電子写真用感光
体を作製した。REFERENCE EXAMPLE 9 An electrophotographic photosensitive member was prepared in the same manner as in Reference Example 1, except that the above-mentioned carrier was changed to 0.9 parts by weight of 4-methoxynaphthalene-1-aldehyde 1-benzyl-1-phenylhydrazone. Produced.
【００３７】参考例１０ 前記正孔搬送物質を４−メトキシナフタレン−１−アル
デヒド１−ベンジル−１−フェニルヒドラゾン０．０９
重量部に変えた他は参考例１と全く同様にして電子写真
用感光体を作製した。Reference Example 10 The above hole-transporting substance was 4-methoxynaphthalene-1-aldehyde 1-benzyl-1-phenylhydrazone 0.09
An electrophotographic photoreceptor was produced in exactly the same manner as in Reference Example 1 except that the amount was changed to parts by weight.
【００３８】参考例１１ 前記正孔搬送物質を４−メトキシナフタレン−１−アル
デヒド１−ベンジル−１−フェニルヒドラゾン９重量部
に変えた他は参考例１と全く同様にして電子写真用感光
体を作製した。REFERENCE EXAMPLE 11 An electrophotographic photosensitive member was prepared in the same manner as in Reference Example 1, except that the above-mentioned hole transporting substance was changed to 9 parts by weight of 4-methoxynaphthalene-1-aldehyde 1-benzyl-1-phenylhydrazone. Produced.
【００３９】参考例１２ 前記正孔搬送物質を４−ジエチルアミノスチレン−β−
アルデヒド１−メチル−１−フェニルヒドラゾン０．９
重量部に変えた他は参考例１と全く同様にして電子写真
用感光体を作製した。Reference Example 12 The above-mentioned hole transporting substance was 4-diethylaminostyrene-β-
Aldehyde 1-methyl-1-phenylhydrazone 0.9
An electrophotographic photoreceptor was produced in exactly the same manner as in Reference Example 1 except that the amount was changed to parts by weight.
【００４０】実施例１ 前記搬送物質を１−Ｎ，Ｎ−ビス（４−メチルフェニ
ル）アミノピレン０．９重量部に変えた他は参考例１と
全く同様にして電子写真用感光体を作製した。Example 1 An electrophotographic photoreceptor was produced in exactly the same manner as in Reference Example 1, except that the carrier substance was changed to 0.9 part by weight of 1-N, N-bis (4-methylphenyl) aminopyrene. .
【００４１】実施例２ 前記正孔搬送物質を１−Ｎ，Ｎ−ビス（４−メチルフェ
ニル）アミノピレン０．０９重量部に変えた他は参考例
１と全く同様にして電子写真用感光体を作製した。Example 2 An electrophotographic photosensitive member was prepared in the same manner as in Example 1 except that the hole transporting material was changed to 0.09 parts by weight of 1-N, N-bis (4-methylphenyl) aminopyrene. Produced.
【００４２】実施例３ 前記正孔搬送物質を１−Ｎ，Ｎ−ビス（４−メチルフェ
ニル）アミノピレン９重量部に変えた他は参考例１と全
く同様にして電子写真用感光体を作製した。Example 3 An electrophotographic photoreceptor was produced in exactly the same manner as in Reference Example 1 except that the hole transporting material was changed to 9 parts by weight of 1-N, N-bis (4-methylphenyl) aminopyrene. .
【００４３】実施例４ 前記正孔搬送物質を１−Ｎ，Ｎ−ビス（３−メチルフェ
ニル）アミノピレン０．９重量部に変えた他は参考例１
と全く同様にして電子写真用感光体を作製した。Example 4 Reference Example 1 except that the hole transporting material was changed to 0.9 part by weight of 1-N, N-bis (3-methylphenyl) aminopyrene.
A photoconductor for electrophotography was prepared in exactly the same manner as in Example 1.
【００４４】参考例１３ 前記搬送物質をＮ，Ｎ−ジフェニル〔１，１’−ビフェ
ニル〕−４−アミン０．９重量部に変えた他は参考例１
と全く同様にして電子写真用感光体を作製した。REFERENCE EXAMPLE 13 Reference Example 1 was repeated except that the carrier was changed to 0.9 parts by weight of N, N-diphenyl [1,1'-biphenyl] -4-amine.
A photoconductor for electrophotography was prepared in exactly the same manner as in Example 1.
【００４５】参考例１４ 前記正孔搬送物質をＮ，Ｎ−ジフェニル〔１，１’−ビ
フェニル〕−４−アミン０．０９重量部に変えた他は参
考例１と全く同様にして電子写真用感光体を作製した。REFERENCE EXAMPLE 14 The same procedure as in Reference Example 1 was repeated except that the hole transporting material was changed to 0.09 parts by weight of N, N-diphenyl [1,1'-biphenyl] -4-amine. A photoreceptor was produced.
【００４６】参考例１５ 前記正孔搬送物質をＮ，Ｎ−ジフェニル〔１，１’−ビ
フェニル〕−４−アミン９重量部に変えた他は参考例１
と全く同様にして電子写真用感光体を作製した。REFERENCE EXAMPLE 15 Reference Example 1 was repeated except that the hole transporting material was changed to 9 parts by weight of N, N-diphenyl [1,1′-biphenyl] -4-amine.
A photoconductor for electrophotography was prepared in exactly the same manner as in Example 1.
【００４７】参考例１６ 前記正孔搬送物質をＮ，Ｎ−ビス（４−メチルフェニ
ル）−〔１，１’−ビフェニル〕−４−アミン０．９重
量部に変えた他は参考例１と全く同様にして電子写真用
感光体を作製した。Reference Example 16 The procedure of Reference Example 1 was repeated except that the hole transporting material was changed to 0.9 parts by weight of N, N-bis (4-methylphenyl)-[1,1'-biphenyl] -4-amine. An electrophotographic photoreceptor was produced in exactly the same manner.
【００４８】参考例１７ 前記搬送物質を９−（４−ジメチルアミノベンジリデ
ン）フルオレン０．９重量部に変えた他は参考例１と全
く同様にして電子写真用感光体を作製した。REFERENCE EXAMPLE 17 An electrophotographic photoreceptor was produced in exactly the same manner as in Reference Example 1, except that the carrier substance was changed to 0.9 parts by weight of 9- (4-dimethylaminobenzylidene) fluorene.
【００４９】参考例１８ 前記正孔搬送物質を９−（４−ジメチルアミノベンジリ
デン）フルオレン０．０９重量部に変えた他は参考例１
と全く同様にして電子写真用感光体を作製した。REFERENCE EXAMPLE 18 Reference Example 1 was repeated except that the hole transporting material was changed to 0.09 parts by weight of 9- (4-dimethylaminobenzylidene) fluorene.
A photoconductor for electrophotography was prepared in exactly the same manner as in Example 1.
【００５０】参考例１９ 前記正孔搬送物質を９−（４−ジメチルアミノベンジリ
デン）フルオレン９重量部に変えた他は参考例１と全く
同様にして電子写真用感光体を作製した。Reference Example 19 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1, except that the hole transporting material was changed to 9 parts by weight of 9- (4-dimethylaminobenzylidene) fluorene.
【００５１】参考例２０ 前記正孔搬送物質を３−（９−フルオレニリデン）−９
−エチルカルバゾール０．９重量部に変えた他は参考例
１と全く同様にして電子写真用感光体を作製した。Reference Example 20 The above-mentioned hole transporting substance was 3- (9-fluorenylidene) -9.
A photoconductor for electrophotography was prepared in exactly the same manner as in Reference Example 1 except that the amount was changed to 0.9 parts by weight of ethylcarbazole.
【００５２】参考例２１ 前記搬送物質を１，１−ビス（４−ジベンジルアミノフ
ェニル）プロパン０．９重量部に変えた他は参考例１と
全く同様にして電子写真用感光体を作製した。REFERENCE EXAMPLE 21 An electrophotographic photoreceptor was produced in exactly the same manner as in Reference Example 1, except that the carrier substance was changed to 0.9 parts by weight of 1,1-bis (4-dibenzylaminophenyl) propane. .
【００５３】参考例２２ 前記正孔搬送物質を１，１−ビス（４−ジベンジルアミ
ノフェニル）プロパン０．０９重量部に変えた他は参考
例１と全く同様にして電子写真用感光体を作製した。REFERENCE EXAMPLE 22 An electrophotographic photosensitive member was prepared in the same manner as in Reference Example 1, except that the hole transport material was changed to 0.09 parts by weight of 1,1-bis (4-dibenzylaminophenyl) propane. Produced.
【００５４】参考例２３ 前記正孔搬送物質を１，１−ビス（４−ジベンジルアミ
ノフェニル）プロパン９重量部に変えた他は参考例１と
全く同様にして電子写真用感光体を作製した。REFERENCE EXAMPLE 23 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1, except that the hole transporting substance was changed to 9 parts by weight of 1,1-bis (4-dibenzylaminophenyl) propane. .
【００５５】参考例２４ 前記正孔搬送物質をトリス（４−ジエチルアミノフェニ
ル）メタン０．９重量部に変えた他は参考例１と全く同
様にして電子写真用感光体を作製した。REFERENCE EXAMPLE 24 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1, except that the hole transporting substance was changed to 0.9 parts by weight of tris (4-diethylaminophenyl) methane.
【００５６】実施例５ 前記搬送物質を１，２−ビス（４−ジエチルアミノスチ
リル）ベンゼン０．９重量部に変えた他は参考例１と全
く同様にして電子写真用感光体を作製した。Example 5 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1, except that the carrier substance was changed to 0.9 parts by weight of 1,2-bis (4-diethylaminostyryl) benzene.
【００５７】実施例６ 前記正孔搬送物質を１，２−ビス（４−ジエチルアミノ
スチリル）ベンゼン０．０９重量部に変えた他は参考例
１と全く同様にして電子写真用感光体を作製した。Example 6 An electrophotographic photoreceptor was produced in exactly the same manner as in Reference Example 1 except that the hole transporting material was changed to 0.09 parts by weight of 1,2-bis (4-diethylaminostyryl) benzene. .
【００５８】実施例７ 前記正孔搬送物質を１，２−ビス（４−ジエチルアミノ
スチリル）ベンゼン９重量部に変えた他は参考例１と全
く同様にして電子写真用感光体を作製した。Example 7 An electrophotographic photosensitive member was prepared in exactly the same manner as in Reference Example 1, except that the hole transporting material was changed to 9 parts by weight of 1,2-bis (4-diethylaminostyryl) benzene.
【００５９】実施例８ 前記正孔搬送物質を１，２−ビス（２，４−ジメトキシ
スチリル）ベンゼン０．９重量部に変えた他は参考例１
と全く同様にして電子写真用感光体を作製した。Example 8 Reference Example 1 except that the hole transporting material was changed to 0.9 parts by weight of 1,2-bis (2,4-dimethoxystyryl) benzene.
A photoconductor for electrophotography was prepared in exactly the same manner as in Example 1.
【００６０】実施例９ 前記搬送物質を４’−ジフェニルアミノ−α−フェニル
スチルベン０．９重量部に変えた他は参考例１と全く同
様にして電子写真用感光体を作製した。Example 9 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1, except that the carrier was changed to 0.9 parts by weight of 4'-diphenylamino-α-phenylstilbene.
【００６１】実施例１０ 前記正孔搬送物質を４’−ジフェニルアミノ−α−フェ
ニルスチルベン０．０９重量部に変えた他は参考例１と
全く同様にして電子写真用感光体を作製した。Example 10 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1, except that the hole transporting material was changed to 0.09 parts by weight of 4'-diphenylamino-α-phenylstilbene.
【００６２】実施例１１ 前記正孔搬送物質を４’−ジフェニルアミノ−α−フェ
ニルスチルベン９重量部に変えた他は参考例１と全く同
様にして電子写真用感光体を作製した。Example 11 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1, except that the hole transporting material was changed to 9 parts by weight of 4'-diphenylamino-α-phenylstilbene.
【００６３】実施例１２ 前記正孔搬送物質を４’−メチルフェニルアミノ−α−
フェニルスチルベン０．９重量部に変えた他は参考例１
と全く同様にして電子写真用感光体を作製した。Example 12 The hole transporting material was 4'-methylphenylamino-α-
Reference Example 1 except that phenylstilbene was changed to 0.9 parts by weight.
A photoconductor for electrophotography was prepared in exactly the same manner as in Example 1.
【００６４】実施例１３ 前記搬送物質を３−スチリル−９−エチルカルバゾール
０．９重量部に変えた他は参考例１と全く同様にして電
子写真用感光体を作製した。Example 13 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1, except that the carrier was changed to 0.9 parts by weight of 3-styryl-9-ethylcarbazole.
【００６５】実施例１４ 前記正孔搬送物質を３−スチリル−９−エチルカルバゾ
ール０．０９重量部に変えた他は参考例１と全く同様に
して電子写真用感光体を作製した。Example 14 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1, except that the hole transporting substance was changed to 0.09 parts by weight of 3-styryl-9-ethylcarbazole.
【００６６】実施例１５ 前記正孔搬送物質を３−スチリル−９−エチルカルバゾ
ール９重量部に変えた他は参考例１と全く同様にして電
子写真用感光体を作製した。Example 15 An electrophotographic photoreceptor was produced in exactly the same manner as in Reference Example 1, except that the hole transporting material was changed to 9 parts by weight of 3-styryl-9-ethylcarbazole.
【００６７】実施例１６ 前記正孔搬送物質を３−（４−メトキシスチリル）−９
−エチルカルバゾール０．９重量部に変えた他は参考例
１と全く同様にして電子写真用感光体を作製した。Example 16 The hole transporting material was 3- (4-methoxystyryl) -9
A photoconductor for electrophotography was prepared in exactly the same manner as in Reference Example 1 except that the amount was changed to 0.9 parts by weight of ethylcarbazole.
【００６８】実施例１７ 前記正孔搬送物質４−ジフェニルアミノスチルベンを
０．９重量部に変えた他は参考例１と全く同様にして電
子写真用感光体を作製した。Example 17 An electrophotographic photosensitive member was prepared in exactly the same manner as in Reference Example 1 except that the amount of the hole transport material 4-diphenylaminostilbene was changed to 0.9 part by weight.
【００６９】実施例１８ 前記正孔搬送物質を４−ジフェニルアミノスチルベン
０．０９重量部に変えた他は参考例１と全く同様にして
電子写真用感光体を作製した。Example 18 An electrophotographic photosensitive member was prepared in exactly the same manner as in Reference Example 1, except that the hole transporting substance was changed to 0.09 parts by weight of 4-diphenylaminostilbene.
【００７０】実施例１９ 前記正孔搬送物質を４−ジフェニルアミノスチルベン９
重量部に変えた他は参考例１と全く同様にして電子写真
用感光体を作製した。Example 19 The above-mentioned hole transporting substance was 4-diphenylaminostilbene 9
An electrophotographic photoreceptor was produced in exactly the same manner as in Reference Example 1 except that the amount was changed to parts by weight.
【００７１】実施例２０ 前記正孔搬送物質を４−ジフェニルアミノスチルベン
０．９重量部に変えた他は参考例１と全く同様にして電
子写真用感光体を作製した。Example 20 A photoconductor for electrophotography was produced in exactly the same manner as in Reference Example 1, except that the hole transporting substance was changed to 0.9 parts by weight of 4-diphenylaminostilbene.
【００７２】実施例２１ 前記搬送物質を９−（４−ジエチルアミノスチリル）ア
ントラセン０．９重量部に変えた他は参考例１と全く同
様にして電子写真用感光体を作製した。Example 21 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1, except that the carrier substance was changed to 0.9 parts by weight of 9- (4-diethylaminostyryl) anthracene.
【００７３】実施例２２ 前記正孔搬送物質を９−（４−ジエチルアミノスチリ
ル）アントラセン０．０９重量部に変えた他は参考例１
と全く同様にして電子写真用感光体を作製した。Example 22 Reference Example 1 was repeated except that the hole transporting material was changed to 0.09 parts by weight of 9- (4-diethylaminostyryl) anthracene.
A photoconductor for electrophotography was prepared in exactly the same manner as in Example 1.
【００７４】実施例２３ 前記正孔搬送物質を９−（４−ジエチルアミノスチリ
ル）アントラセン９重量部に変えた他は参考例１と全く
同様にして電子写真用感光体を作製した。Example 23 A photoconductor for electrophotography was prepared in exactly the same manner as in Reference Example 1, except that the hole transporting material was changed to 9 parts by weight of 9- (4-diethylaminostyryl) anthracene.
【００７５】実施例２４ 前記正孔搬送物質を９−ブロム−１０−（４−ジエチル
アミノスチリル）アントラセン０．９重量部に変えた他
は参考例１と全く同様にして電子写真用感光体を作製し
た。Example 24 An electrophotographic photoreceptor was prepared in exactly the same manner as in Reference Example 1 except that the hole transporting material was changed to 0.9 parts by weight of 9-bromo-10- (4-diethylaminostyryl) anthracene. did.
【００７６】実施例２５ 前記搬送物質を１−フェニル−３−（４−ジエチルアミ
ノスチリル）−５−（４−ジエチルアミノフェニル）ピ
ラゾリン０．９重量部に変えた他は参考例１と全く同様
にして電子写真用感光体を作製した。Example 25 In the same manner as in Reference Example 1, except that the carrier substance was changed to 0.9 part by weight of 1-phenyl-3- (4-diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazoline. An electrophotographic photoreceptor was prepared.
【００７７】実施例２６ 前記正孔搬送物質を１−フェニル−３−（４−ジエチル
アミノスチリル）−５−（４−ジエチルアミノフェニ
ル）ピラゾリン０．０９重量部に変えた他は参考例１と
全く同様にして電子写真用感光体を作製した。Example 26 Except that the hole transporting material was changed to 0.09 parts by weight of 1-phenyl-3- (4-diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazolin, the same as Reference Example 1 Thus, an electrophotographic photosensitive member was prepared.
【００７８】実施例２７ 前記正孔搬送物質を１−フェニル−３−（４−ジエチル
アミノスチリル）−５−（４−ジエチルアミノフェニ
ル）ピラゾリン９重量部に変えた他は参考例１と全く同
様にして電子写真用感光体を作製した。Example 27 Except that the hole transport material was changed to 9 parts by weight of 1-phenyl-3- (4-diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazolin, the same procedure as in Reference Example 1 was repeated. An electrophotographic photoreceptor was prepared.
【００７９】実施例２８ 前記正孔搬送物質を１−フェニル−３−（４−ジメチル
アミノスチリル）−５−（４−ジメチルアミノフェニ
ル）ピラゾリン０．９重量部に変えた他は参考例１と全
く同様にして電子写真用感光体を作製した。Example 28 Reference Example 1 was repeated except that the hole transporting material was changed to 0.9 part by weight of 1-phenyl-3- (4-dimethylaminostyryl) -5- (4-dimethylaminophenyl) pyrazolin. An electrophotographic photoreceptor was produced in exactly the same manner.
【００８０】比較例 前記正孔搬送物質を加えない他は参考例１と全く同様に
して電子写真用感光体を作製した。Comparative Example A photoconductor for electrophotography was produced in exactly the same manner as in Reference Example 1 except that the hole transporting substance was not added.
【００８１】上記のようにして得た電子写真用感光体に
対して、リコー製複写機ＦＴ６５５０を用いて，２０℃
６５％及び１０℃１５％の環境下での複写機内の残留電
位を評価し、更に１０万枚の画像テストを行い、画像テ
スト前後の保護層の膜厚測定を実施しその摩耗量の評価
を行った。評価結果を表１に示す。The electrophotographic photoreceptor obtained as described above was applied to a copying machine FT6550 manufactured by Ricoh at 20 ° C.
The residual potential in the copying machine under the environment of 65% and 10 ° C. and 15% was evaluated, an image test of 100,000 sheets was further performed, the thickness of the protective layer was measured before and after the image test, and the wear amount was evaluated. went. Table 1 shows the evaluation results.
【００８２】[0082]
【表１】 [Table 1]
【００８３】[0083]
【表２】 [Table 2]
【００８４】[0084]
【表３】 [Table 3]
【００８５】[0085]
【表４】 [Table 4]
【００８６】表１に示されるように、本発明に係る参考
例１〜参考例２４、実施例１〜２８の電子写真用感光体
は２０℃６５％及び１０℃１５％下での残留電位が大き
く低減されており、更に正孔搬送物質と結着樹脂との重
量比が１：９９〜５０：５０の範囲にあるので、１０万
枚複写後の表面保護層の膜厚減少量も著しく小さいこと
がわかる。また、参考例１〜参考例２４、実施例１〜２
８の電子写真用感光体は初期から１０万枚後まで品質の
高い画像が安定して継続的に得られるものであった。As shown in Table 1, the electrophotographic photoreceptors of Reference Examples 1 to 24 and Examples 1 to 28 according to the present invention have a residual potential at 20 ° C. of 65% and 10 ° C. of 15%. Since the weight ratio between the hole transport material and the binder resin is in the range of 1:99 to 50:50, the decrease in the thickness of the surface protective layer after copying 100,000 sheets is extremely small. You can see that. Reference Examples 1 to 24, Examples 1 and 2
In the electrophotographic photoreceptor No. 8, a high-quality image was stably and continuously obtained from the initial stage to after 100,000 copies.
【００８７】[0087]
【発明の効果】以上説明したように、本発明に係る表面
保護層を有する電子写真用感光体は高い機械的強度をそ
なえ、かつ複写機内の残留電位及びその環境変動量も著
しく小さい安定した電機特性を示し、更に高品質な画像
が長期に亘って安定して得られる信頼性の高いものであ
る。As described above, the electrophotographic photoreceptor having the surface protective layer according to the present invention has a high mechanical strength and a stable electric machine in which the residual potential in the copying machine and its environmental fluctuation are extremely small. It is a highly reliable image that exhibits characteristics and that can provide a high-quality image stably over a long period of time.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 六反園 節 東京都大田区中馬込１丁目３番６号 株 式会社リコー内 (56)参考文献 特開 昭60−169856（ＪＰ，Ａ) 特開 平３−7945（ＪＰ，Ａ) 特開 平１−109356（ＪＰ，Ａ) 特開 平２−178668（ＪＰ，Ａ) 特開 平４−338961（ＪＰ，Ａ) 特開 昭62−159151（ＪＰ，Ａ) 特開 昭64−17063（ＪＰ，Ａ) 特開 昭55−157748（ＪＰ，Ａ) ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Rokutanen Section 1-3-6 Nakamagome, Ota-ku, Tokyo Inside Ricoh Co., Ltd. (56) References JP-A-60-169856 (JP, A) JP-A-3-7945 (JP, A) JP-A-1-109356 (JP, A) JP-A-2-178668 (JP, A) JP-A-4-3388961 (JP, A) JP-A-62-159151 (JP, A) JP, A) JP-A-64-17063 (JP, A) JP-A-55-157748 (JP, A)
Claims (2)
層を順次積層した電子写真用感光体において、該表面保
護層が結着樹脂中に正孔搬送物質として一般式（１）乃
至（７）で示される化合物を少なくとも１つを含有し、
且つ表面保護層の全重量の４３重量％以上６０重量％以
下の導電性を有する金属酸化物の微粉末を含有させたこ
とを特徴とする電子写真用感光体。 【化１】 〔式中、Ａ1，Ａ2は置換もしくは無置換のアルキル基又
は置換もしくは無置換のアリール基を表わし、それぞれ
同一でも異なっていてもよく、Ａｒは置換又は無置換の
縮合多環式炭化水素基を表わす〕 【化２】 〔式中、Ｒはカルバゾリル基、ピリジル基、チエニル
基、インドリル基、フリル基あるいはそれぞれ置換もし
くは無置換のフェニル基、スチリル基、ナフチル基又は
アントリル基を表わし、該置換基はジアルキルアミノ
基、アルキル基、アルコキシ基、カルボキシ基もしくは
そのエステル基、ハロゲン原子、シアノ基、アラルキル
アミノ基、Ｎ−アルキル−Ｎ−アラルキルアミノ基、ア
ミノ基、ニトロ基およびアセチルアミノ基からなる群か
ら選ばれた基を表わす〕 【化３】 〔式中、ｎは０又は１の整数、Ｒ1は水素原子、アルキ
ル基又は置換もしくは無置換のフェニル基を表し、Ａは 【化４】 ９−アントリル基又は置換もしくは無置換のＮ−アルキ
ルカルバゾリル基を表わし、ここでＲ2は水素原子、ア
ルキル基、アルコキシ基、ハロゲン原子又は 【化５】 （但し、Ｒ3およびＲ4はアルキル基、置換もしくは無置
換のアラルキル基、置換もしくは無置換のアリール基を
示し、Ｒ3およびＲ4は環を形成してもよい）を表わし、
ｍは０，１，２又は３の整数であって、ｍが２以上のと
きはＲ2は同一でも異なってもよい〕 【化６】 〔式中、Ｒ1は低級アルキル基又はベンジル基を表わ
し、Ｒ2は水素原子、低級アルキル基、低級アルコキシ
基、ハロゲン原子、ニトロ基、アミノ基又は低級アルキ
ル基もしくはベンジル基で置換されたアミノ基を表わ
し、ｎは１又は２の整数を表わす〕 【化７】 〔式中、Ｒ1は水素原子、アルキル基、アルコキシ基又
はハロゲン原子を表わし、Ｒ2およびＲ3はアルキル基、
置換もしくは無置換のアラルキル基又は置換もしくは無
置換のアリール基を表わし、Ｒ4は水素原子又は置換も
しくは無置換のフェニル基を表わし、また、Ａｒはフェ
ニル基又はナフチル基を表わす〕 【化８】 〔式中、Ｒは水素又はハロゲン原子を表わし、Ａｒは置
換もしくは無置換のフェニル基、ナフチル基、アントリ
ル基又はカルバゾリル基を表わす〕 【化９】 〔式中、Ｒ1，Ｒ2およびＲ3は水素、低級アルキル基、
低級アルコキシ基、ジアルキルアミノ基又はハロゲン原
子を表わし、ｎは０又は１を表わす〕1. An electrophotographic photoreceptor having a photoconductive layer and a surface protective layer sequentially laminated on a conductive support, wherein the surface protective layer has the general formula (1) containing at least one compound represented by the formula (7) ,
A photoconductor for electrophotography, comprising a fine powder of a metal oxide having conductivity of 43% by weight or more and 60% by weight or less of the total weight of the surface protective layer. Embedded image [In the formula, A 1 and A 2 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, which may be the same or different, and Ar is a substituted or unsubstituted fused polycyclic hydrocarbon. Represents a group] [In the formula, R represents a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, a furyl group or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group or an anthryl group, and the substituent is a dialkylamino group, an alkyl group A group selected from the group consisting of a group, an alkoxy group, a carboxy group or an ester group thereof, a halogen atom, a cyano group, an aralkylamino group, an N-alkyl-N-aralkylamino group, an amino group, a nitro group and an acetylamino group. Represents) Wherein n is an integer of 0 or 1, R 1 is a hydrogen atom, an alkyl group or a substituted or unsubstituted phenyl group, and A is Represents a 9-anthryl group or a substituted or unsubstituted N-alkylcarbazolyl group, wherein R 2 is a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or Wherein R 3 and R 4 represent an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, and R 3 and R 4 may form a ring.
m is an integer of 0, 1, 2 or 3, and when m is 2 or more, R 2 may be the same or different. Wherein R 1 represents a lower alkyl group or a benzyl group; R 2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group or an amino group substituted with a lower alkyl group or a benzyl group; And n represents an integer of 1 or 2.] [In the formula, R 1 represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, and R 2 and R 3 represent an alkyl group,
Represents a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group; R 4 represents a hydrogen atom or a substituted or unsubstituted phenyl group; and Ar represents a phenyl group or a naphthyl group. [Wherein, R represents hydrogen or a halogen atom, and Ar represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group or carbazolyl group]. Wherein R 1 , R 2 and R 3 are hydrogen, a lower alkyl group,
Represents a lower alkoxy group, a dialkylamino group or a halogen atom, and n represents 0 or 1]
が１：９９〜５０：５０であることを特徴とする請求項
１に記載された電子写真用感光体。2. The electrophotographic photoconductor according to claim 1, wherein the weight ratio of the hole transport material to the binder resin is 1:99 to 50:50.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06906691A JP3286711B2 (en) | 1991-03-08 | 1991-03-08 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06906691A JP3286711B2 (en) | 1991-03-08 | 1991-03-08 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04281461A JPH04281461A (en) | 1992-10-07 |
| JP3286711B2 true JP3286711B2 (en) | 2002-05-27 |
Family
ID=13391832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP06906691A Expired - Lifetime JP3286711B2 (en) | 1991-03-08 | 1991-03-08 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3286711B2 (en) |
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-
1991
- 1991-03-08 JP JP06906691A patent/JP3286711B2/en not_active Expired - Lifetime
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| JPH04281461A (en) | 1992-10-07 |
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