JPH10239871A - Electrophotographic photoreceptor - Google Patents

Electrophotographic photoreceptor

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Publication number
JPH10239871A
JPH10239871A JP4236097A JP4236097A JPH10239871A JP H10239871 A JPH10239871 A JP H10239871A JP 4236097 A JP4236097 A JP 4236097A JP 4236097 A JP4236097 A JP 4236097A JP H10239871 A JPH10239871 A JP H10239871A
Authority
JP
Japan
Prior art keywords
compound
group
charge transfer
represented
aryl group
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.)
Pending
Application number
JP4236097A
Other languages
Japanese (ja)
Inventor
Nobuaki Hirota
展章 廣田
Hideya Arisue
英也 有末
Makoto Okaji
誠 岡地
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Paper Mills Ltd
Original Assignee
Mitsubishi Paper Mills Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsubishi Paper Mills Ltd filed Critical Mitsubishi Paper Mills Ltd
Priority to JP4236097A priority Critical patent/JPH10239871A/en
Publication of JPH10239871A publication Critical patent/JPH10239871A/en
Pending legal-status Critical Current

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  • Compositions Of Macromolecular Compounds (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

PROBLEM TO BE SOLVED: To provide an electrophotographic photoreceptor high in sensitivity and small in change of charge potential and residual potential due to repeating uses and superior in mechanical strength, especially, abrasion resistance by incorporating a specified copolymer in a charge transfer layer. SOLUTION: This electrophotographic photoreceptor contains the copolymers comprising structural units each represented by formulae I and II and as a charge transfer agent at least one of compounds represented by formula III or the like in the charge transfer layer, and in formulae I-III, each of R<1> and R<2> is an H atom or an alkyl or aryl group or each may combine with each other to form a 5-, 6-, 7-, or 8-membered cyclic hydro-carbon ring; each of R<3> and R<4> is an H or halogen atom or an alkyl or aryl group; each of R<5> and R<6> is an H or halogen atom or an alkyl or aryl group; and each of R<7> -R<10> is an H atom or an alkyl or aralkyl or aryl group and each of R<9> and R<10> may combine with each other to form a ring.

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【０００１】[0001]

【発明の属する技術分野】本発明は電子写真感光体に関
するものであり、詳しくは高感度で繰り返し安定性に優
れ、機械的強度、特に耐摩耗性に優れた電子写真感光体
に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photoreceptor, and more particularly, to an electrophotographic photoreceptor having high sensitivity, excellent repetition stability, and excellent mechanical strength, especially abrasion resistance.

【０００２】[0002]

【従来の技術】従来、電子写真方式の感光体としては、
セレン、硫化カドミウム、酸化亜鉛、シリコン等の無機
光導電体を主成分とする感光層を有するものが広く知ら
れていた。しかし、これらは感度、熱安定性、耐湿性、
耐久性等において必ずしも満足し得るものではなく、ま
た特にセレン及び硫化カドミウムはその毒性のために製
造上、取扱上にも制約があった。2. Description of the Related Art Conventionally, as an electrophotographic photosensitive member,
Those having a photosensitive layer mainly containing an inorganic photoconductor such as selenium, cadmium sulfide, zinc oxide, and silicon have been widely known. However, these are sensitive, heat stable, moisture resistant,
It is not always satisfactory in durability and the like, and in particular, selenium and cadmium sulfide have restrictions in production and handling due to their toxicity.

【０００３】一方、有機光導電性化合物を主成分とする
感光層を有する電子写真感光体は、製造が比較的容易で
あること、安価であること、取扱いが容易であること、
また一般にセレン感光体に比べて熱安定性が優れている
こと等多くの利点を有し、近年多くの注目を集めてい
る。On the other hand, an electrophotographic photosensitive member having a photosensitive layer containing an organic photoconductive compound as a main component is relatively easy to manufacture, inexpensive, easy to handle,
In addition, it generally has many advantages such as superior thermal stability as compared with selenium photoreceptors, and has attracted much attention in recent years.

【０００４】このような有機光導電性化合物としては、
ポリ−Ｎ−ビニルカルバゾールがよく知られており、こ
れと２，４，７−トリニトロ−９−フルオレノン等のル
イス酸とから形成される電荷移動錯体を主成分とする感
光層を有する電子写真感光体が、特公昭５０−１０４９
６号公報に記載されている。しかしながらこの感光体
は、感度、成膜性、及び耐久性において必ずしも満足で
きるものではなかった。[0004] Such organic photoconductive compounds include:
Poly-N-vinylcarbazole is well known, and has an electrophotographic photosensitive member having a photosensitive layer mainly composed of a charge transfer complex formed from this and a Lewis acid such as 2,4,7-trinitro-9-fluorenone. The body is 50-5049
No. 6 is described. However, this photoreceptor was not always satisfactory in sensitivity, film formability, and durability.

【０００５】これに対し、トリフェニルアミン類、スチ
ルベン類、ヒドラゾン類に代表される電荷移動剤とフタ
ロシアニン、アゾ顔料等の電荷発生剤を組み合わせた低
分子量の有機光導電性化合物を含む電子写真感光体が提
案されている。これらを適当なバインダーと組み合わ
せ、更に電荷発生能力の高い化合物と電荷移動能力の高
い化合物を、例えば積層型感光体として組み合わせるこ
とにより、セレン等の無機感光体に近い感度を有するも
のも出現している。その結果、複写機やプリンター等の
分野で、このような有機光導電性化合物を主成分とする
感光体が大きく進出してきている。On the other hand, an electrophotographic photosensitive material containing a low molecular weight organic photoconductive compound obtained by combining a charge transfer agent represented by triphenylamines, stilbenes and hydrazones with a charge generating agent such as phthalocyanine and azo pigment. The body has been proposed. By combining these with an appropriate binder, and further combining a compound having a high charge generation ability and a compound having a high charge transfer ability, for example, as a laminated photoreceptor, one having a sensitivity close to that of an inorganic photoreceptor such as selenium has also appeared. I have. As a result, photoconductors containing such an organic photoconductive compound as a main component have largely entered the field of copying machines and printers.

【０００６】電荷発生機能と電荷移動機能とをそれぞれ
別個の物質に分担させるようにした積層型あるいは分散
型の機能分離型感光体は、各々の材料の選択範囲が広
く、帯電特性、感度、耐久性等の電子写真特性におい
て、任意の特性を有する電子写真感光体を比較的容易に
作製できるという利点を持っている。[0006] A layered or dispersed function-separated type photoreceptor in which the charge generation function and the charge transfer function are shared by separate substances, respectively, has a wide selection range of each material, and has a wide charging range, charging characteristics, sensitivity and durability. It has the advantage that an electrophotographic photoreceptor having any desired characteristics can be relatively easily produced.

【０００７】従来、電荷発生剤あるいは電荷移動剤とし
て種々のものが提案されている。例えば、無定形セレン
からなる電荷発生層とポリ−Ｎ−ビニルカルバゾールを
主成分とする電荷移動層とを組み合わせた感光層を有す
る電子写真感光体が実用化されていた。しかし、無定形
セレンからなる電荷発生層は耐久性に劣るという欠点を
有している。また、有機染料や有機顔料を電荷発生剤と
して用いることが、種々提案されており、例えば、モノ
アゾ顔料やビスアゾ顔料を感光層中に含有する電子写真
感光体として、特公昭４８−３０５１３号公報、特開昭
５２−４２４１号公報、特開昭５４−４６５５８号公
報、特公昭５６−１１９４５号公報等が既に公知となっ
ている。Conventionally, various charge generating agents or charge transfer agents have been proposed. For example, an electrophotographic photoreceptor having a photosensitive layer in which a charge generation layer made of amorphous selenium and a charge transfer layer containing poly-N-vinylcarbazole as a main component has been put to practical use. However, the charge generation layer made of amorphous selenium has a drawback of poor durability. Also, various proposals have been made to use an organic dye or an organic pigment as a charge generating agent, for example, as an electrophotographic photoreceptor containing a monoazo pigment or a bisazo pigment in a photosensitive layer, JP-B-48-30513, JP-A-52-4241, JP-A-54-46558, and JP-B-56-11945 have already been known.

【０００８】しかしながら、機能分離型感光体として実
用化されているものは極く僅かであり、また要求される
多くの特性、例えば帯電特性、感度、残留電位、前露光
特性、繰り返し使用特性等の電気的特性や耐傷性、耐摩
耗性等の機械的強度等の全てを満足しているとはいい難
いのが現状である。これらの特性は、電荷発生剤及び電
荷移動剤やそれらを分散し、又は相溶するバインダー樹
脂の各々の性能に依存するところが大きいといえるが、
それらの適合する組合せの選択が重要であることも知ら
れており、数多くの組合せが提案されてきている。その
理由は、かかる選択が理論的な根拠に基づくものという
よりはむしろ、試行錯誤的に行われているためであると
考えられる。[0008] However, there are only a few practically usable photoreceptors of the function-separated type, and many required characteristics such as charging characteristics, sensitivity, residual potential, pre-exposure characteristics, and repeated use characteristics. At present, it is difficult to say that all of the electrical characteristics, mechanical strength such as scratch resistance and abrasion resistance are satisfied. It can be said that these properties largely depend on the performance of each of the charge generating agent and the charge transfer agent and the performance of the binder resin in which they are dispersed or compatible.
It is also known that the selection of those matching combinations is important, and many combinations have been proposed. This may be because such choices are made on a trial and error basis, rather than on a theoretical basis.

【０００９】[0009]

【発明が解決しようとする課題】本発明の目的は、高感
度にして、繰り返しによる帯電電位並びに残留電位の変
化が小さく、機械的強度、特に耐摩耗性に優れた電子写
真感光体を提供することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide an electrophotographic photoreceptor which has a high sensitivity, has a small change in charge potential and residual potential due to repetition, and has excellent mechanical strength, especially abrasion resistance. It is in.

【００１０】[0010]

【課題を解決するための手段】本発明者らは上記の目的
を達成するために鋭意検討を重ねた結果、導電性支持体
上に少なくとも電荷発生層と電荷移動層からなる感光層
を有する電子写真感光体において、電荷移動層に下記一
般式（I）及び（II）で表される構造単位からなる共重
合体化合物を含有させ、かつ電荷移動剤として下記一般
式（III）、（IV）、（V）で表される化合物の少なくと
も１種を含有させることが、前記課題を解決するのに有
効であることを見いだし本発明を完成するに至った。Means for Solving the Problems The present inventors have made intensive studies to achieve the above object, and as a result, have found that an electron having at least a photosensitive layer comprising a charge generation layer and a charge transfer layer on a conductive support. In a photographic photoreceptor, the charge transfer layer contains a copolymer compound comprising structural units represented by the following general formulas (I) and (II), and the following general formulas (III) and (IV) as charge transfer agents It has been found that the inclusion of at least one compound represented by formula (V) is effective in solving the above-mentioned problems, and the present invention has been completed.

【００１１】[0011]

【化６】 Embedded image

【００１２】式（I）中において、Ｒ1、Ｒ2は水素原
子、アルキル基、アリール基、Ｒ1とＲ2で形成する炭素
数５〜８の環状炭化水素残基を表し、Ｒ3、Ｒ4は水素原
子、ハロゲン原子、アルキル基、アリール基を表す。ま
た、ａ、ｂは１又は２の整数であり、各々ベンゼン環に
置換しているＲ3、Ｒ4の個数を表し、ａ＝２のときＲ3
は同一でも異なっていても構わないし、ｂ＝２のときＲ
4は同一でも異なっていても構わない。ここで、上記の
アルキル基、アリール基は置換基を有していても構わな
い。[0012] In formula (I), R 1, R 2 represents a hydrogen atom, an alkyl group, an aryl group, a cyclic hydrocarbon residue having a carbon formed by R 1 and R 2 5 to 8, R 3, R 4 represents a hydrogen atom, a halogen atom, an alkyl group, or an aryl group. Further, a, b is an integer of 1 or 2, represents the number of R 3, R 4 are substituted on each benzene ring, when a = 2 R 3
May be the same or different, and when b = 2, R
4 may be the same or different. Here, the above-mentioned alkyl group and aryl group may have a substituent.

【００１３】[0013]

【化７】 Embedded image

【００１４】式（II）中において、Ｒ5、Ｒ6は水素原
子、ハロゲン原子、アルキル基、アリール基を表す。ま
た、ｃ、ｄは１又は２の整数であり、各々ベンゼン環に
置換しているＲ5、Ｒ6の個数を表し、ｃ＝２のときＲ5
は同一でも異なっていても構わないし、ｄ＝２のときＲ
6は同一でも異なっていても構わない。ここで、上記の
アルキル基、アリール基は置換基を有していても構わな
い。In the formula (II), R 5 and R 6 represent a hydrogen atom, a halogen atom, an alkyl group or an aryl group. Further, c, d is an integer of 1 or 2, represents R 5, the number of R 6 which is substituted in each benzene ring, when c = 2 R 5
May be the same or different, and when d = 2, R
6 may be the same or different. Here, the above-mentioned alkyl group and aryl group may have a substituent.

【００１５】[0015]

【化８】 Embedded image

【００１６】式（III）中において、Ｒ7、Ｒ8、Ｒ9、Ｒ
10は水素原子、アルキル基、アラルキル基、アリール基
を示し、Ｒ9とＲ10は相互に結合して環を形成してもよ
い。Ｚはインドリン環の２つの炭素原子と共に飽和の５
〜８員環を形成するのに必要とされる原子群を示す。こ
こで、上記のアルキル基、アラルキル基、アリール基は
置換基を有していても構わない。In the formula (III), R 7 , R 8 , R 9 , R
10 represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group, and R 9 and R 10 may be mutually bonded to form a ring. Z is saturated 5 with two carbon atoms of the indoline ring.
The following shows the atoms required for forming an 8-membered ring. Here, the above-mentioned alkyl group, aralkyl group, and aryl group may have a substituent.

【００１７】[0017]

【化９】 Embedded image

【００１８】式（IV）中において、Ｒ11及びＲ12はアル
キル基、アラルキル基、アリール基又は複素環基を表
す。Ｒ13及びＲ14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す。ここで、上記のアルキル
基、アラルキル基、アリール基、複素環基、アルコキシ
基は置換基を有していても構わない。In the formula (IV), R 11 and R 12 represent an alkyl group, an aralkyl group, an aryl group or a heterocyclic group. R 13 and R 14 represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. Here, the alkyl group, the aralkyl group, the aryl group, the heterocyclic group, and the alkoxy group may have a substituent.

【００１９】[0019]

【化１０】 Embedded image

【００２０】式（V）中において、Ｒ15、Ｒ16は、水素
原子、アルキル基、アリール基又はスチリル基を表し、
少なくとも１つはアリール基又はスチリル基である。Ｒ
17はアルキル基、アラルキル基、又はアリール基を表
し、Ｒ18、Ｒ19は、水素原子、アルキル基、アラルキル
基又はアリール基を表し、Ｒ20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す。ここで、
上記のアルキル基、アリール基、スチリル基、アラルキ
ル基、アルコキシ基は置換基を有していても構わない。In the formula (V), R 15 and R 16 represent a hydrogen atom, an alkyl group, an aryl group or a styryl group,
At least one is an aryl group or a styryl group. R
17 represents an alkyl group, an aralkyl group or an aryl group, R 18 and R 19 represent a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and R 20 represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. Represents here,
The above-mentioned alkyl group, aryl group, styryl group, aralkyl group, and alkoxy group may have a substituent.

【００２１】本発明は、具体的には導電性支持体上に必
要に応じブロッキング層を設け、その上に少なくとも電
荷発生層と電荷移動層からなる感光層を有する電子写真
感光体であって、この電荷移動層にバインダー樹脂とし
て上記一般式（I）及び（II）で表される構造単位から
なる共重合体化合物を含有し、かつ電荷移動剤として上
記一般式（III）、（IV）、（V）で表される化合物の少
なくとも１種を含有する電子写真感光体である。The present invention specifically relates to an electrophotographic photoreceptor having a photosensitive layer comprising at least a charge generation layer and a charge transfer layer on which a blocking layer is provided as necessary on a conductive support, The charge transfer layer contains, as a binder resin, a copolymer compound composed of the structural units represented by the above general formulas (I) and (II), and as a charge transfer agent, the above general formula (III), (IV), An electrophotographic photosensitive member containing at least one compound represented by (V).

【００２２】[0022]

【発明の実施の形態】以下、本発明の電子写真感光体に
おける各構成要素について詳細に説明する。本発明の電
子写真感光体は、導電性支持体上に少なくとも電荷発生
層と電荷移動層からなる感光層を有する電子写真感光体
であって、この電荷移動層にバインダー樹脂として上記
一般式（I）及び（II）で表される構造単位からなる共
重合体化合物を含有し、かつ電荷移動剤として上記一般
式（III）、（IV）、（V）で表される化合物の少なくと
も１種を含有する電子写真感光体である。DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, each component of the electrophotographic photoreceptor of the present invention will be described in detail. The electrophotographic photoreceptor of the present invention is an electrophotographic photoreceptor having at least a photosensitive layer comprising a charge generation layer and a charge transfer layer on a conductive support, wherein the charge transfer layer has the above general formula (I) as a binder resin. ) And (II), wherein at least one of the compounds represented by the above general formulas (III), (IV) and (V) is used as a charge transfer agent. It is an electrophotographic photosensitive member.

【００２３】感光層は、少なくとも電荷発生層と電荷移
動層から成り、電荷発生層と電荷移動層の積層順序は、
導電性支持体に近い方から電荷発生層、電荷移動層の順
でも、電荷移動層、電荷発生層の順のどちらでも構わな
いが、本発明においては、導電性支持体に近い方から電
荷発生層、電荷移動層の順に設けることが好ましい。The photosensitive layer comprises at least a charge generation layer and a charge transfer layer, and the order of lamination of the charge generation layer and the charge transfer layer is as follows.
Although the charge generation layer and the charge transfer layer may be arranged in this order from the side closest to the conductive support, the charge transfer layer and the charge generation layer may be arranged in this order. It is preferable to provide the layer and the charge transfer layer in this order.

【００２４】電荷移動層に用いられるバインダー樹脂と
しては、下記一般式（I）及び（II）で表される構造単
位からなる共重合体化合物が、単独もしくは他のバイン
ダー樹脂と共に用いられる。As the binder resin used in the charge transfer layer, a copolymer compound having a structural unit represented by the following general formulas (I) and (II) is used alone or together with another binder resin.

【００２５】[0025]

【化１１】 Embedded image

【００２６】式（I）中において、Ｒ1、Ｒ2は水素原
子、アルキル基、アリール基、Ｒ1とＲ2で形成する炭素
数５〜８の環状炭化水素残基を表し、Ｒ3、Ｒ4は水素原
子、ハロゲン原子、アルキル基、アリール基を表す。ま
た、ａ、ｂは１又は２の整数であり、各々ベンゼン環に
置換しているＲ3、Ｒ4の個数を表し、ａ＝２のときＲ3
は同一でも異なっていても構わないし、ｂ＝２のときＲ
4は同一でも異なっていても構わない。ここで、上記の
アルキル基、アリール基は置換基を有していても構わな
い。[0026] In formula (I), R 1, R 2 represents a hydrogen atom, an alkyl group, a cyclic hydrocarbon residue aryl group, carbon atoms formed by R 1 and R 2 5 to 8, R 3, R 4 represents a hydrogen atom, a halogen atom, an alkyl group, or an aryl group. Further, a, b is an integer of 1 or 2, represents the number of R 3, R 4 are substituted on each benzene ring, when a = 2 R 3
May be the same or different, and when b = 2, R
4 may be the same or different. Here, the above-mentioned alkyl group and aryl group may have a substituent.

【００２７】[0027]

【化１２】 Embedded image

【００２８】式（II）中において、Ｒ5、Ｒ6は水素原
子、ハロゲン原子、アルキル基、アリール基を表す。ま
た、ｃ、ｄは１又は２の整数であり、各々ベンゼン環に
置換しているＲ5、Ｒ6の個数を表し、ｃ＝２のときＲ5
は同一でも異なっていても構わないし、ｄ＝２のときＲ
6は同一でも異なっていても構わない。ここで、上記の
アルキル基、アリール基は置換基を有していても構わな
い。In the formula (II), R 5 and R 6 represent a hydrogen atom, a halogen atom, an alkyl group or an aryl group. Further, c, d is an integer of 1 or 2, represents R 5, the number of R 6 which is substituted in each benzene ring, when c = 2 R 5
May be the same or different, and when d = 2, R
6 may be the same or different. Here, the above-mentioned alkyl group and aryl group may have a substituent.

【００２９】上記共重合体化合物を構成する一般式
（I）で表される構造単位の具体例としては、以下の化
合物が挙げられるがこれらに限定されない。Specific examples of the structural unit represented by the general formula (I) constituting the copolymer compound include, but are not limited to, the following compounds.

【００３０】[0030]

【化１３】 Embedded image

【００３１】[0031]

【化１４】 Embedded image

【００３２】[0032]

【化１５】 Embedded image

【００３３】[0033]

【化１６】 Embedded image

【００３４】[0034]

【化１７】 Embedded image

【００３５】[0035]

【化１８】 Embedded image

【００３６】[0036]

【化１９】 Embedded image

【００３７】上記共重合体化合物を構成する一般式（I
I）で表される構造単位の具体例としては、以下の化合
物が挙げられるがこれらに限定されない。The general formula (I) constituting the above copolymer compound
Specific examples of the structural unit represented by I) include, but are not limited to, the following compounds.

【００３８】[0038]

【化２０】 Embedded image

【００３９】[0039]

【化２１】 Embedded image

【００４０】[0040]

【化２２】 Embedded image

【００４１】上記一般式（I）及び（II）で表される構
造単位からなる共重合体化合物の具体例を下記表１から
表６で例示化合物として示すがこれらに限定されない。
ここで、構造単位Ｍ１は一般式（I）で表される構造単
位の具体例を示し、構造単位Ｍ２は一般式（II）で表さ
れる構造単位の具体例を示し、Ｍ１／Ｍ２は例示化合物
中に含まれる構造単位Ｍ１と構造単位Ｍ２のモル比を示
す。本発明において構造単位Ｍ１と構造単位Ｍ２のモル
比（Ｍ１／Ｍ２）は、９９／１から４０／６０の範囲が
好ましく、更に、９５／５から６０／４０の範囲である
ことがより好ましい。また、共重合体化合物の分子量
は、重量平均分子量が５０００から２０００００の範囲
が好ましく、更に、１００００から１０００００の範囲
がより好ましい。以下に示す例示化合物はランダム共重
合体、ブロック共重合体又は一部ブロック共重合部分を
含有するランダム共重合体のいずれであっても構わな
い。Specific examples of the copolymer compound comprising the structural units represented by the above general formulas (I) and (II) are shown in Tables 1 to 6 below as exemplary compounds, but are not limited thereto.
Here, the structural unit M1 represents a specific example of the structural unit represented by the general formula (I), the structural unit M2 represents a specific example of the structural unit represented by the general formula (II), and M1 / M2 is exemplified. The molar ratio of the structural unit M1 to the structural unit M2 contained in the compound is shown. In the present invention, the molar ratio (M1 / M2) of the structural unit M1 to the structural unit M2 is preferably in the range of 99/1 to 40/60, and more preferably in the range of 95/5 to 60/40. The weight average molecular weight of the copolymer compound is preferably in the range of 5,000 to 200,000, and more preferably in the range of 10,000 to 100,000. The exemplified compounds shown below may be any of a random copolymer, a block copolymer or a random copolymer containing a partial block copolymer.

【００４２】[0042]

【表１】 [Table 1]

【００４３】[0043]

【表２】 [Table 2]

【００４４】[0044]

【表３】 [Table 3]

【００４５】[0045]

【表４】 [Table 4]

【００４６】[0046]

【表５】 [Table 5]

【００４７】[0047]

【表６】 [Table 6]

【００４８】電荷移動層において、上記一般式（I）及
び（II）で表される構造単位からなる共重合体化合物と
共に用いられるバインダー樹脂としては、スチレン、塩
化ビニル、酢酸ビニル、アクリル酸エステル、メタクリ
ル酸エステル等のビニル化合物の重合体及び共重合体、
ポリカーボネート樹脂、ポリアリレート樹脂、ポリエス
テル樹脂、フェノキシ樹脂、ポリスルホン、セルロース
エステル樹脂、セルロースエーテル樹脂、ウレタン樹
脂、エポキシ樹脂、シリコーン樹脂等の各種ポリマーが
挙げられる。In the charge transfer layer, styrene, vinyl chloride, vinyl acetate, acrylate, and the like may be used as the binder resin together with the copolymer compound having the structural units represented by the above general formulas (I) and (II). Polymers and copolymers of vinyl compounds such as methacrylates,
Various polymers such as polycarbonate resin, polyarylate resin, polyester resin, phenoxy resin, polysulfone, cellulose ester resin, cellulose ether resin, urethane resin, epoxy resin, and silicone resin are exemplified.

【００４９】電荷移動層の形成に用いられる溶媒として
は、テトラヒドロフラン、ジオキソラン、メチルエチル
ケトン、ベンゼン、トルエン、モノクロロベンゼン、
１，２−ジクロロエタン、ジクロロメタン、クロロホル
ム、酢酸エチル等が挙げられる。As the solvent used for forming the charge transfer layer, tetrahydrofuran, dioxolan, methyl ethyl ketone, benzene, toluene, monochlorobenzene,
Examples thereof include 1,2-dichloroethane, dichloromethane, chloroform, and ethyl acetate.

【００５０】電荷移動層用バインダー樹脂は、電荷移動
剤１００重量部に対し１０から５００重量部、好ましく
は５０から２００重量部の範囲で用いられる。電荷移動
層の厚さは１から１００μｍ、好ましくは１０から５０
μｍの範囲で用いられる。The binder resin for the charge transfer layer is used in an amount of 10 to 500 parts by weight, preferably 50 to 200 parts by weight, based on 100 parts by weight of the charge transfer agent. The thickness of the charge transfer layer is 1 to 100 μm, preferably 10 to 50 μm.
It is used in the range of μm.

【００５１】電荷移動層はヒドラゾン化合物やスチリル
化合物等の電荷移動剤とバインダー樹脂を適当な溶媒に
溶解し、塗布、乾燥することによって設けることができ
る。The charge transfer layer can be provided by dissolving a charge transfer agent such as a hydrazone compound or a styryl compound and a binder resin in an appropriate solvent, coating and drying.

【００５２】従来より電荷移動剤として用いられている
化合物には、オキサジアゾール化合物、トリフェニルメ
タン化合物、ピラゾリン化合物、ヒドラゾン化合物、ト
リアリールアミン化合物、スチリル化合物等が挙げられ
るが、本発明においては、下記一般式（III）、（I
V）、（V）で表される化合物を用いる。これらは各々単
独でも２種以上混合して用いても構わないし、他の電荷
移動剤と共に用いても構わない。Compounds conventionally used as charge transfer agents include oxadiazole compounds, triphenylmethane compounds, pyrazoline compounds, hydrazone compounds, triarylamine compounds, styryl compounds, and the like. , The following general formula (III), (I
The compounds represented by (V) and (V) are used. These may be used alone or in combination of two or more, or may be used together with other charge transfer agents.

【００５３】[0053]

【化２３】 Embedded image

【００５４】式（III）中において、Ｒ7、Ｒ8、Ｒ9、Ｒ
10は水素原子、アルキル基、アラルキル基、アリール基
を示し、Ｒ9とＲ10は相互に結合して環を形成してもよ
い。Ｚはインドリン環の２つの炭素原子と共に飽和の５
〜８員環を形成するのに必要とされる原子群を示す。こ
こで、上記のアルキル基、アラルキル基、アリール基は
置換基を有していても構わない。In the formula (III), R 7 , R 8 , R 9 , R
10 represents a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group, and R 9 and R 10 may be mutually bonded to form a ring. Z is saturated 5 with two carbon atoms of the indoline ring.
The following shows the atoms required for forming an 8-membered ring. Here, the above-mentioned alkyl group, aralkyl group, and aryl group may have a substituent.

【００５５】[0055]

【化２４】 Embedded image

【００５６】式（IV）中において、Ｒ11及びＲ12はアル
キル基、アラルキル基、アリール基又は複素環基を表
す。Ｒ13及びＲ14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す。ここで、上記のアルキル
基、アラルキル基、アリール基、複素環基、アルコキシ
基は置換基を有していても構わない。In the formula (IV), R 11 and R 12 represent an alkyl group, an aralkyl group, an aryl group or a heterocyclic group. R 13 and R 14 represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. Here, the alkyl group, the aralkyl group, the aryl group, the heterocyclic group, and the alkoxy group may have a substituent.

【００５７】[0057]

【化２５】 Embedded image

【００５８】式（V）中において、Ｒ15、Ｒ16は、水素
原子、アルキル基、アリール基又はスチリル基を表し、
少なくとも１つはアリール基又はスチリル基である。Ｒ
17はアルキル基、アラルキル基、又はアリール基を表
し、Ｒ18、Ｒ19は、水素原子、アルキル基、アラルキル
基又はアリール基を表し、Ｒ20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す。ここで、
上記のアルキル基、アリール基、スチリル基、アラルキ
ル基、アルコキシ基は置換基を有していても構わない。In the formula (V), R 15 and R 16 represent a hydrogen atom, an alkyl group, an aryl group or a styryl group;
At least one is an aryl group or a styryl group. R
17 represents an alkyl group, an aralkyl group or an aryl group, R 18 and R 19 represent a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and R 20 represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. Represents here,
The above-mentioned alkyl group, aryl group, styryl group, aralkyl group, and alkoxy group may have a substituent.

【００５９】上記一般式（III）で表される化合物の具
体例としては次のものが挙げられるがこれらに限定され
ない。また、以下の化合物には、立体異性体を有するも
のがあるが、異性体が混在していても、それぞれ単独で
あっても構わない。Specific examples of the compound represented by the above general formula (III) include, but are not limited to, the following. Some of the following compounds have stereoisomers, but the isomers may be mixed or may be used alone.

【００６０】[0060]

【化２６】 Embedded image

【００６１】[0061]

【化２７】 Embedded image

【００６２】[0062]

【化２８】 Embedded image

【００６３】[0063]

【化２９】 Embedded image

【００６４】[0064]

【化３０】 Embedded image

【００６５】[0065]

【化３１】 Embedded image

【００６６】[0066]

【化３２】 Embedded image

【００６７】[0067]

【化３３】 Embedded image

【００６８】[0068]

【化３４】 Embedded image

【００６９】上記一般式（IV）で表される化合物の具体
例としては、次のものが挙げられるがこれらに限定され
ない。Specific examples of the compound represented by the above general formula (IV) include, but are not limited to, the following.

【００７０】[0070]

【化３５】 Embedded image

【００７１】[0071]

【化３６】 Embedded image

【００７２】[0072]

【化３７】 Embedded image

【００７３】[0073]

【化３８】 Embedded image

【００７４】[0074]

【化３９】 Embedded image

【００７５】[0075]

【化４０】 Embedded image

【００７６】[0076]

【化４１】 Embedded image

【００７７】[0077]

【化４２】 Embedded image

【００７８】[0078]

【化４３】 Embedded image

【００７９】[0079]

【化４４】 Embedded image

【００８０】[0080]

【化４５】 Embedded image

【００８１】[0081]

【化４６】 Embedded image

【００８２】上記一般式（V）で表される化合物の具体
例としては、次のものが挙げられるがこれらに限定され
ない。また、以下の化合物には、立体異性体を有するも
のがあるが、異性体が混在していても、それぞれ単独で
あっても構わない。Specific examples of the compound represented by the general formula (V) include, but are not limited to, the following. Some of the following compounds have stereoisomers, but the isomers may be mixed or may be used alone.

【００８３】[0083]

【化４７】 Embedded image

【００８４】[0084]

【化４８】 Embedded image

【００８５】[0085]

【化４９】 Embedded image

【００８６】[0086]

【化５０】 Embedded image

【００８７】[0087]

【化５１】 Embedded image

【００８８】[0088]

【化５２】 Embedded image

【００８９】[0089]

【化５３】 Embedded image

【００９０】感光層を構成する電荷発生層は、少なくと
も電荷発生剤を含有し、電荷発生剤単独もしくは電荷発
生剤とバインダー樹脂とを溶媒中で混合分散し、塗布乾
燥することによって形成される。The charge generation layer constituting the photosensitive layer contains at least a charge generation agent, and is formed by mixing and dispersing the charge generation agent alone or the charge generation agent and a binder resin in a solvent, followed by coating and drying.

【００９１】電荷発生層に用いられる電荷発生剤として
は、フタロシアニン顔料、ナフタロシアニン顔料、ペリ
レン顔料、多環キノン顔料、アゾ顔料、ポルフィリン顔
料、キナクリドン顔料等が挙げられる。本発明において
は、無金属フタロシアニン、オキシチタニウムフタロシ
アニン、アゾ顔料の少なくとも１種を電荷発生層に含有
させることにより、感光体の更なる高感度化及び繰り返
し安定性の向上が可能であり特に好ましい。また、アゾ
顔料としては、モノアゾ顔料、ビスアゾ顔料、トリスア
ゾ顔料のいずれも用いられるが、中でも下記一般式（V
I）で表されるビスアゾ顔料が特に好ましく、より一層
の高感度化が可能である。Examples of the charge generating agent used in the charge generating layer include phthalocyanine pigments, naphthalocyanine pigments, perylene pigments, polycyclic quinone pigments, azo pigments, porphyrin pigments, quinacridone pigments and the like. In the present invention, by including at least one of a metal-free phthalocyanine, an oxytitanium phthalocyanine, and an azo pigment in the charge generation layer, it is possible to further increase the sensitivity of the photoreceptor and to improve the repetition stability. As the azo pigment, any of a monoazo pigment, a bisazo pigment and a trisazo pigment can be used. Among them, the following general formula (V
The bisazo pigments represented by I) are particularly preferable, and can further increase the sensitivity.

【００９２】[0092]

【化５４】 Embedded image

【００９３】一般式（VI）において、Ａは水素原子、ア
ルキル基、アリール基、複素環基を表し、ｍ及びｎは０
又は１を表し、Ｂはカップラー残基を表す。ここで、上
記のアルキル基、アリール基、複素環基は置換基を有し
ていても構わない。In the general formula (VI), A represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group;
Or 1 and B represents a coupler residue. Here, the above-mentioned alkyl group, aryl group, and heterocyclic group may have a substituent.

【００９４】一般式（VI）において、Ａは水素原子、ア
ルキル基、アリール基、複素環基を表し、それらの具体
例としては次のものが挙げられるがこれらに限定されな
い。In the general formula (VI), A represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group, and specific examples thereof include, but are not limited to, the following.

【００９５】[0095]

【化５５】 Embedded image

【００９６】[0096]

【化５６】 Embedded image

【００９７】[0097]

【化５７】 Embedded image

【００９８】[0098]

【化５８】 Embedded image

【００９９】一般式（VI）において、Ｂはカップラー残
基を表し、それらの具体例としては次のものが挙げられ
るがこれらに限定されない。In the general formula (VI), B represents a coupler residue, and specific examples thereof include, but are not limited to, the following.

【０１００】[0100]

【化５９】 Embedded image

【０１０１】[0101]

【化６０】 Embedded image

【０１０２】[0102]

【化６１】 Embedded image

【０１０３】[0103]

【化６２】 Embedded image

【０１０４】[0104]

【化６３】 Embedded image

【０１０５】[0105]

【化６４】 Embedded image

【０１０６】[0106]

【化６５】 Embedded image

【０１０７】[0107]

【化６６】 Embedded image

【０１０８】[0108]

【化６７】 Embedded image

【０１０９】[0109]

【化６８】 Embedded image

【０１１０】上記一般式（VI）で表されるビスアゾ顔料
の具体例を表７から表１０に示すが、これらに限定され
ない。Specific examples of the bisazo pigment represented by the general formula (VI) are shown in Tables 7 to 10, but are not limited thereto.

【０１１１】[0111]

【表７】 [Table 7]

【０１１２】[0112]

【表８】 [Table 8]

【０１１３】[0113]

【表９】 [Table 9]

【０１１４】[0114]

【表１０】 [Table 10]

【０１１５】電荷発生層に用いられるバインダー樹脂と
しては、従来より知られているスチレン、酢酸ビニル、
塩化ビニル、アクリル酸エステル、メタクリル酸エステ
ル等のビニル化合物の重合体及び共重合体、ホルマール
樹脂、ブチラール樹脂等のアセタール樹脂、シリコーン
樹脂、フェノキシ樹脂、エポキシ樹脂、ウレタン樹脂、
フェノール樹脂、ポリアミド樹脂、ポリイミド樹脂、ポ
リカーボネート樹脂、ポリエステル樹脂、ポリアリレー
ト樹脂等が挙げられるが、これらに限定されない。Examples of the binder resin used in the charge generation layer include conventionally known styrene, vinyl acetate,
Vinyl chloride, acrylic acid esters, polymers and copolymers of vinyl compounds such as methacrylic acid esters, formal resins, acetal resins such as butyral resins, silicone resins, phenoxy resins, epoxy resins, urethane resins,
Examples include, but are not limited to, phenolic resins, polyamide resins, polyimide resins, polycarbonate resins, polyester resins, polyarylate resins, and the like.

【０１１６】電荷発生層に用いられるバインダー樹脂
は、電荷発生剤１００重量部に対し、１から１０００重
量部、好ましくは１から４００重量部の範囲で用いられ
る。また、電荷発生層の厚さは０．０５から２０μｍ、
好ましくは０．１から２μｍの範囲で用いられる。The binder resin used in the charge generating layer is used in an amount of 1 to 1000 parts by weight, preferably 1 to 400 parts by weight, based on 100 parts by weight of the charge generating agent. The charge generation layer has a thickness of 0.05 to 20 μm,
Preferably, it is used in the range of 0.1 to 2 μm.

【０１１７】用いられる溶媒としては、１，２−ジメト
キシエタン、テトラヒドロフラン、１，４−ジオキサ
ン、１，３−ジオキソラン等のエーテル類、メチルエチ
ルケトン、シクロヘキサノン等のケトン類、トルエン、
キシレン等の芳香族炭化水素、Ｎ，Ｎ−ジメチルホルム
アミド、アセトニトリル、Ｎ−メチルピロリドン、ジメ
チルスルホキシド等の非プロトン性極性溶媒、メタノー
ル、エタノール、イソプロパノール等のアルコール類、
酢酸メチル、酢酸エチル、酢酸ブチル、メチルセロソル
ブアセテート等のエステル類、ジクロロエタン、ジクロ
ロメタン、クロロホルム等のハロゲン化炭化水素類等が
挙げられる。Examples of the solvent used include ethers such as 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane, and 1,3-dioxolan; ketones such as methyl ethyl ketone and cyclohexanone; toluene;
Aromatic hydrocarbons such as xylene, aprotic polar solvents such as N, N-dimethylformamide, acetonitrile, N-methylpyrrolidone, and dimethylsulfoxide; alcohols such as methanol, ethanol and isopropanol;
Esters such as methyl acetate, ethyl acetate, butyl acetate and methyl cellosolve acetate; and halogenated hydrocarbons such as dichloroethane, dichloromethane and chloroform.

【０１１８】本発明の電子写真感光体の感光層が形成さ
れる導電性支持体としては周知の電子写真感光体に採用
されているものがいずれも使用できる。具体的には、例
えば金、銀、白金、チタニウム、アルミニウム、銅、亜
鉛、鉄、導電処理を施した金属酸化物等のドラム、シー
ト、ベルトあるいはこれらの薄膜のラミネート物、蒸着
物等が挙げられる。As the electroconductive support on which the photosensitive layer of the electrophotographic photoreceptor of the present invention is formed, any of those used for known electrophotographic photoreceptors can be used. Specific examples include gold, silver, platinum, titanium, aluminum, copper, zinc, iron, and drums, sheets, belts, or laminates of these thin films, vapor-deposits, and the like of metal oxides and the like subjected to conductive treatment. Can be

【０１１９】更に、金属粉末、金属酸化物、カーボンブ
ラック、炭素繊維、ヨウ化銅、電荷移動錯体、無機塩、
イオン伝導性の高分子電解質等の導電性物質を適当なバ
インダーと共に塗布し、ポリマーマトリックス中に埋め
込んで導電処理を施したプラスチックやセラミック、紙
等で構成されるドラム、シート、ベルト等が挙げられ
る。Further, metal powder, metal oxide, carbon black, carbon fiber, copper iodide, charge transfer complex, inorganic salt,
Drums, sheets, belts, etc. made of plastics, ceramics, papers, etc., which are obtained by applying a conductive material such as an ion-conductive polymer electrolyte together with a suitable binder and embedding in a polymer matrix to give a conductive treatment. .

【０１２０】本発明の電子写真感光体の構成中には、感
光層と導電性支持体の間に、感光層から導電性支持体へ
の電荷の注入をコントロールするためのブロッキング層
を必要に応じ設け、また感光層表面には感光体の耐久性
を向上させるために表面保護層を設けても構わない。In the construction of the electrophotographic photoreceptor of the present invention, a blocking layer for controlling charge injection from the photosensitive layer to the conductive support is provided between the photosensitive layer and the conductive support, if necessary. A surface protective layer may be provided on the surface of the photosensitive layer to improve the durability of the photosensitive member.

【０１２１】ブロッキング層は、バインダー樹脂単独、
あるいはバインダー樹脂と無機顔料等との混合で構成さ
れる。バインダー樹脂としては、ポリアミド系樹脂、エ
ポキシ系樹脂、ウレタン系樹脂等が挙げられる。また、
無機顔料としては、酸化チタン、酸化亜鉛、酸化ジルコ
ニウム等が挙げられる。The blocking layer is composed of a binder resin alone,
Alternatively, it is composed of a mixture of a binder resin and an inorganic pigment. Examples of the binder resin include a polyamide resin, an epoxy resin, and a urethane resin. Also,
Examples of the inorganic pigment include titanium oxide, zinc oxide, zirconium oxide, and the like.

【０１２２】また、感光層は成膜性、可撓性、機械的強
度を向上させるために周知の可塑剤を含有していてもよ
い。可塑剤としては、フタル酸エステル、リン酸エステ
ル、塩素化パラフィン、塩素化脂肪酸エステル、メチル
ナフタレン等の芳香族化合物等が挙げられる。The photosensitive layer may contain a well-known plasticizer in order to improve film-forming properties, flexibility and mechanical strength. Examples of the plasticizer include phthalic acid esters, phosphoric acid esters, chlorinated paraffins, chlorinated fatty acid esters, and aromatic compounds such as methylnaphthalene.

【０１２３】更に、感光体の電子写真特性の改良のため
に、酸化防止剤等の添加物を含有させても構わない。Further, in order to improve the electrophotographic characteristics of the photoreceptor, additives such as an antioxidant may be contained.

【０１２４】[0124]

【実施例】次に本発明を実施例により更に詳細に説明す
るが、本発明はこれらに何ら限定されるものではない。EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

【０１２５】実施例１ 例示化合物（ＣＧ−７）で示される電荷発生剤１重量部
とポリビニルブチラール樹脂（電気化学工業製、デンカ
ブチラール＃３０００−Ｋ）１重量部を１，２−ジメト
キシエタン１００重量部に混合し、ペイントコンディシ
ョナーによりガラスビーズ（シンマルエンタープライゼ
ズ製、ハイビーＤ−２０）と共に４時間分散した。こう
して得た顔料分散液をアプリケーターにて金属アルミニ
ウム薄板（ＪＩＳ規格＃１０５０）上に塗布し、８０℃
で１５分乾燥して膜厚約０．２μｍの電荷発生層を得
た。Example 1 1 part by weight of a charge generating agent represented by the exemplary compound (CG-7) and 1 part by weight of a polyvinyl butyral resin (Denka Butyral # 3000-K, manufactured by Denki Kagaku Kogyo Kogyo) were mixed with 1,2-dimethoxyethane 100 The resulting mixture was mixed with glass beads (manufactured by Shinmaru Enterprises, Hybee D-20) for 4 hours using a paint conditioner. The pigment dispersion thus obtained is applied on a metal aluminum sheet (JIS # 1050) using an applicator,
For 15 minutes to obtain a charge generation layer having a thickness of about 0.2 μm.

【０１２６】次に例示化合物（ＣＴ１−６）で示される
電荷移動剤１０重量部と例示化合物（ＣＰ−２）で示さ
れる共重合体化合物（重量平均分子量；３２０００）１
０重量部とＤＬ−α−トコフェロール０．１重量部をジ
クロロメタン１５０重量部に溶解させて、上記電荷発生
層の上に、この溶液をアプリケーターにより塗布し、８
０℃で６０分乾燥して乾燥膜厚２０μｍの電荷移動層を
形成した。Next, 10 parts by weight of a charge transfer agent represented by the exemplified compound (CT1-6) and a copolymer compound (weight average molecular weight: 32000) represented by the exemplified compound (CP-2) 1
0 parts by weight and 0.1 parts by weight of DL-α-tocopherol are dissolved in 150 parts by weight of dichloromethane, and this solution is applied on the above-mentioned charge generating layer by an applicator.
After drying at 0 ° C. for 60 minutes, a charge transfer layer having a dry film thickness of 20 μm was formed.

【０１２７】この様にして作製した積層型電子写真感光
体を室温暗中に一昼夜保管した後、静電記録試験装置
（川口電機製作所製、ＳＰ−４２８）により電子写真特
性評価を行った。測定条件は、コロナ印加電圧：−５ｋ
Ｖ、スタティックモードＮｏ．３（プロセス速度１６７
ｍｍ／ｓ）、照射光（白色光）照度：２ｌｘであった。
その結果、帯電電位−７１０Ｖ、半減露光量１．２ｌｘ
・ｓと非常に高感度の値を示した。結果を表１１に示
す。The thus-prepared laminated electrophotographic photosensitive member was stored in the dark at room temperature for 24 hours, and then evaluated for electrophotographic characteristics by an electrostatic recording tester (SP-428, manufactured by Kawaguchi Electric Works). The measurement conditions were as follows: Corona applied voltage: -5k
V, static mode No. 3 (process speed 167
mm / s) and irradiation light (white light) illuminance: 2 lx.
As a result, the charging potential was -710 V, the half-exposure amount was 1.2 lx.
・ The value of s was very high. Table 11 shows the results.

【０１２８】次に、この感光体をアルミニウム製のドラ
ム素管に張り付け、ドラム感光体評価装置（ジェンテッ
ク製、シンシア９０）により帯電及び光除電の繰り返し
特性を評価した。測定は、コロナ印加電圧：−５．２ｋ
Ｖ、プロセス速度１６０ｍｍ／ｓ、ＴＣＣＤ２モードで
の５０００回の帯電及び光除電の繰り返しを行った。光
除電はタングステンランプアレイを用いて行った。帯電
後の表面電位即ち帯電電位、光除電後の表面電位即ち残
留電位の測定結果を表１１に示す。帯電電位及び残留電
位の変化が極めて小さいことがわかる。Next, this photoreceptor was attached to a drum tube made of aluminum, and the repetition characteristics of charging and light elimination were evaluated by a drum photoreceptor evaluation apparatus (Gentech, Cynthia 90). The measurement was performed with a corona applied voltage of -5.2 k.
V, the process speed was 160 mm / s, and the charge and light elimination were repeated 5000 times in TCCD2 mode. Light elimination was performed using a tungsten lamp array. Table 11 shows the measurement results of the surface potential after charging, that is, the charging potential, and the surface potential after light removal, that is, the residual potential. It can be seen that changes in the charging potential and the residual potential are extremely small.

【０１２９】また、同様にして作製した感光体の摩耗量
をスガ摩耗試験機を用いて測定した。測定条件は、粗さ
２０００番のサンドペーパーを使用し、加重４００ｇ、
繰り返し回数３００回で行った。感光体の耐摩耗性につ
いては、摩耗量＜１．９ｍｇを◎、１．９ｍｇ≦摩耗量
＜２．２ｍｇを○、２．２ｍｇ≦摩耗量＜２．５ｍｇを
△、２．５ｍｇ≦摩耗量、という基準で評価した。結果
を表１２に示す。Further, the abrasion loss of the photoreceptor produced in the same manner was measured using a Suga abrasion tester. The measurement conditions were as follows: using a sandpaper with a roughness of 2000, weight 400g,
The test was repeated 300 times. Regarding the abrasion resistance of the photoreceptor, abrasion amount <1.9 mg, ◎ 1.9 mg ≦ abrasion amount <2.2 mg, o, 2.2 mg ≦ abrasion amount <2.5 mg, Δ, 2.5 mg ≦ abrasion amount The evaluation was based on the following criteria. Table 12 shows the results.

【０１３０】実施例２ 実施例１において、例示化合物（ＣＴ１−６）で表され
る電荷移動剤の代わりに、例示化合物（ＣＴ１−９）を
用いた以外は実施例１と同様にして電子写真感光体を作
製し、実施例１と同様の試験を行った。Example 2 Electrophotography was carried out in the same manner as in Example 1 except that the exemplified compound (CT1-9) was used instead of the charge transfer agent represented by the exemplified compound (CT1-6). A photoreceptor was manufactured and the same test as in Example 1 was performed.

【０１３１】実施例３ 実施例１において、例示化合物（ＣＴ１−６）で表され
る電荷移動剤の代わりに、例示化合物（ＣＴ１−１３）
を用いた以外は実施例１と同様にして電子写真感光体を
作製し、実施例１と同様の試験を行った。Example 3 In Example 1, the compound (CT1-13) was used instead of the charge transfer agent represented by the compound (CT1-6).
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except for using, and the same test as in Example 1 was performed.

【０１３２】実施例４ 実施例１において、例示化合物（ＣＴ１−６）で表され
る電荷移動剤の代わりに、例示化合物（ＣＴ１−１１）
を用い、例示化合物（ＣＰ−２）で表される共重合体化
合物の代わりに、例示化合物（ＣＰ−４）（重量平均分
子量；３１０００）を用いた以外は実施例１と同様にし
て電子写真感光体を作製し、実施例１と同様の試験を行
った。Example 4 In Example 1, the exemplified compound (CT1-11) was used instead of the charge transfer agent represented by the exemplified compound (CT1-6).
And electrophotography was performed in the same manner as in Example 1 except that Exemplified Compound (CP-4) (weight average molecular weight; 31,000) was used instead of the copolymer compound represented by Exemplified Compound (CP-2). A photoreceptor was manufactured and the same test as in Example 1 was performed.

【０１３３】実施例５ 実施例１において、例示化合物（ＣＧ−７）で表される
電荷発生剤の代わりに、例示化合物（ＣＧ−１４）を用
い、例示化合物（ＣＴ１−６）で表される電荷移動剤の
代わりに、例示化合物（ＣＴ１−１５）を用い、例示化
合物（ＣＰ−２）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−６）（重量平均分子量；３３０
００）を用いた以外は実施例１と同様にして電子写真感
光体を作製し、実施例１と同様の試験を行った。Example 5 The procedure of Example 1 was repeated, except that the charge generating agent represented by Exemplified Compound (CG-7) was used instead of Exemplified Compound (CG-14). Instead of the charge transfer agent, the exemplary compound (CT1-15) is used, and instead of the copolymer compound represented by the exemplary compound (CP-2), the exemplary compound (CP-6) (weight average molecular weight; 330)
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except for using (00), and the same test as in Example 1 was performed.

【０１３４】実施例６ 実施例１において、例示化合物（ＣＧ−７）で表される
電荷発生剤の代わりに、例示化合物（ＣＧ−１４）を用
い、例示化合物（ＣＴ１−６）で表される電荷移動剤の
代わりに、例示化合物（ＣＴ１−１３）を用い、例示化
合物（ＣＰ−２）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−３）（重量平均分子量；３００
００）を用いた以外は実施例１と同様にして電子写真感
光体を作製し、実施例１と同様の試験を行った。Example 6 The procedure of Example 1 was repeated, except that the charge generating agent represented by Exemplified Compound (CG-7) was replaced by Exemplified Compound (CG-14). Instead of the charge transfer agent, the exemplary compound (CT1-13) is used, and instead of the copolymer compound represented by the exemplary compound (CP-2), the exemplary compound (CP-3) (weight average molecular weight: 300)
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except for using (00), and the same test as in Example 1 was performed.

【０１３５】実施例７ 実施例１において、例示化合物（ＣＧ−７）で表される
電荷発生剤の代わりに、例示化合物（ＣＧ−１４）を用
い、例示化合物（ＣＴ１−６）で表される電荷移動剤の
代わりに、例示化合物（ＣＴ１−１０）を用い、例示化
合物（ＣＰ−２）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−２１）（重量平均分子量；３４
０００）を用いた以外は実施例１と同様にして電子写真
感光体を作製し、実施例１と同様の試験を行った。Example 7 The procedure of Example 1 was repeated, except that the charge generating agent represented by Exemplified Compound (CG-7) was replaced by Exemplified Compound (CG-14). Instead of the charge transfer agent, the exemplary compound (CT1-10) is used, and instead of the copolymer compound represented by the exemplary compound (CP-2), the exemplary compound (CP-21) (weight average molecular weight; 34)
000), an electrophotographic photosensitive member was prepared in the same manner as in Example 1, and the same test as in Example 1 was performed.

【０１３６】実施例８ 実施例１において、例示化合物（ＣＧ−７）で表される
電荷発生剤の代わりに、例示化合物（ＣＧ−１５）を用
い、例示化合物（ＣＴ１−６）で表される電荷移動剤の
代わりに、例示化合物（ＣＴ１−２１）を用い、例示化
合物（ＣＰ−２）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−１）（重量平均分子量；３１０
００）を用いた以外は実施例１と同様にして電子写真感
光体を作製し、実施例１と同様の試験を行った。Example 8 The procedure of Example 1 was repeated, except that the charge generating agent represented by the exemplified compound (CG-7) was replaced by the exemplified compound (CG-15). Instead of the charge transfer agent, the exemplary compound (CT1-21) is used, and instead of the copolymer compound represented by the exemplary compound (CP-2), the exemplary compound (CP-1) (weight average molecular weight; 310)
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except for using (00), and the same test as in Example 1 was performed.

【０１３７】実施例９ 実施例１において、例示化合物（ＣＧ−７）で表される
電荷発生剤の代わりに、例示化合物（ＣＧ−１５）を用
い、例示化合物（ＣＴ１−６）で表される電荷移動剤の
代わりに、例示化合物（ＣＴ１−２５）を用い、例示化
合物（ＣＰ−２）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−４９）（重量平均分子量２６０
００）を用いた以外は実施例１と同様にして電子写真感
光体を作製し、実施例１と同様の試験を行った。Example 9 The procedure of Example 1 was repeated, except that the charge generating agent represented by Exemplified Compound (CG-7) was replaced by Exemplified Compound (CG-15). Instead of the charge transfer agent, the exemplary compound (CT1-25) is used, and instead of the copolymer compound represented by the exemplary compound (CP-2), the exemplary compound (CP-49) (weight average molecular weight 260
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except for using (00), and the same test as in Example 1 was performed.

【０１３８】実施例１０ 実施例１において、例示化合物（ＣＧ−７）で表される
電荷発生剤の代わりに、下記例示化合物（ＣＧ−４５）
を用いた以外は実施例１と同様にして電子写真感光体を
作製し、実施例１と同様の試験を行った。Example 10 In Example 1, the following exemplified compound (CG-45) was used instead of the charge generating agent represented by the exemplified compound (CG-7).
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except for using, and the same test as in Example 1 was performed.

【０１３９】[0139]

【化６９】 Embedded image

【０１４０】次に、以下の比較例で用いる比較化合物を
示す。Next, comparative compounds used in the following comparative examples are shown.

【０１４１】[0141]

【化７０】 Embedded image

【０１４２】比較例１ 実施例１において、例示化合物（ＣＰ−２）で表される
共重合体化合物の代わりに、ポリエステル樹脂（東洋紡
製、バイロン２９０）を用いた以外は実施例１と同様に
して電子写真感光体を作製し、実施例１と同様の試験を
行った。Comparative Example 1 The procedure of Example 1 was repeated, except that a polyester resin (manufactured by Toyobo, Byron 290) was used instead of the copolymer compound represented by the exemplified compound (CP-2). Thus, an electrophotographic photosensitive member was manufactured, and the same test as in Example 1 was performed.

【０１４３】比較例２ 実施例４において、例示化合物（ＣＰ−４）で表される
共重合体化合物の代わりに、ポリカーボネート樹脂（帝
人化成製、パンライトＬ−１２５０）を用いた以外は実
施例４と同様にして電子写真感光体を作製し、実施例４
と同様の試験を行った。Comparative Example 2 In Example 4, a polycarbonate resin (manufactured by Teijin Chemicals Ltd., Panlite L-1250) was used in place of the copolymer compound represented by the exemplified compound (CP-4). An electrophotographic photoreceptor was prepared in the same manner as in Example 4.
The same test was performed.

【０１４４】比較例３ 実施例５において、例示化合物（ＣＰ−６）で表される
共重合体化合物の代わりに、ポリアリレート樹脂（ユニ
チカ製、Ｕ−１００Ｄ）を用いた以外は実施例５と同様
にして電子写真感光体を作製し、実施例５と同様の試験
を行った。Comparative Example 3 The procedure of Example 5 was repeated, except that a polyarylate resin (U-100D, manufactured by Unitika) was used in place of the copolymer compound represented by the exemplary compound (CP-6). An electrophotographic photoreceptor was manufactured in the same manner, and the same test as in Example 5 was performed.

【０１４５】比較例４ 実施例７において、例示化合物（ＣＴ１−１０）で表さ
れる電荷移動剤の代わりに、比較化合物（ＥＸ−１）を
用いた以外は実施例７と同様にして電子写真感光体を作
製し、実施例７と同様の試験を行った。Comparative Example 4 An electrophotograph was prepared in the same manner as in Example 7, except that the comparative compound (EX-1) was used in place of the charge transfer agent represented by the exemplified compound (CT1-10). A photoreceptor was manufactured and the same test as in Example 7 was performed.

【０１４６】比較例５ 実施例８において、例示化合物（ＣＴ１−２１）で表さ
れる電荷移動剤の代わりに、比較化合物（ＥＸ−２）を
用いた以外は実施例８と同様にして電子写真感光体を作
製し、実施例８と同様の試験を行った。Comparative Example 5 An electrophotograph was prepared in the same manner as in Example 8, except that the comparative compound (EX-2) was used in place of the charge transfer agent represented by the exemplified compound (CT1-21). A photoconductor was prepared, and the same test as in Example 8 was performed.

【０１４７】実施例１から１０までの電気特性の結果を
を表１１に示し、耐摩耗性試験の結果を表１２に示す。
また、比較例１から５までの電気特性の結果を表１３に
示し、耐摩耗性の結果を表１４に示す。Table 11 shows the results of the electrical characteristics of Examples 1 to 10, and Table 12 shows the results of the wear resistance test.
Table 13 shows the results of the electrical characteristics of Comparative Examples 1 to 5, and Table 14 shows the results of the wear resistance.

【０１４８】[0148]

【表１１】 [Table 11]

【０１４９】[0149]

【表１２】 [Table 12]

【０１５０】[0150]

【表１３】 [Table 13]

【０１５１】[0151]

【表１４】 [Table 14]

【０１５２】上記のように、実施例１から１０で例示し
た感光体は、高感度で繰り返し安定性に優れ、かつ耐摩
耗性に優れているが、実施例１０では感度及び繰り返し
安定性が、実施例１から９に比べるとやや劣っている。
一方、比較例１から５で例示した感光体は、全体的に低
感度で繰り返し安定性に劣り、耐摩耗性も劣っている。
比較例４、５は耐摩耗性の面ではそれほど劣っていない
が、感度及び繰り返し安定性が劣っている。このように
繰り返し安定性が劣っていると、コピー実写評価では、
繰り返しにより実写画像のコントラストが低下すると共
にカブリが発生する。As described above, the photoconductors exemplified in Examples 1 to 10 are high in sensitivity, excellent in repetition stability, and excellent in abrasion resistance. It is slightly inferior to Examples 1 to 9.
On the other hand, the photoconductors exemplified in Comparative Examples 1 to 5 are generally low in sensitivity, inferior in repeated stability, and inferior in wear resistance.
Comparative Examples 4 and 5 are not so inferior in terms of wear resistance, but are inferior in sensitivity and repetition stability. If the repeat stability is inferior in this way, in the actual copy evaluation,
The repetition lowers the contrast of the real image and fog occurs.

【０１５３】実施例１１ 例示化合物（ＣＧ−８）で示される電荷発生剤１重量部
とポリビニルブチラール樹脂（積水化学工業製、エスレ
ックＢＭ−Ｓ）１重量部をメチルイソブチルケトン１０
０重量部に混合し、ペイントコンディショナーによりガ
ラスビーズ（シンマルエンタープライゼズ製、ハイビー
Ｄ−２０）と共に４時間分散した。こうして得た顔料分
散液をアプリケーターにて金属アルミニウム薄板（ＪＩ
Ｓ規格＃１０５０）上に塗布し、８０℃で１５分乾燥し
て膜厚約０．２μｍの電荷発生層を得た。Example 11 1 part by weight of a charge generating agent represented by the exemplified compound (CG-8) and 1 part by weight of a polyvinyl butyral resin (Eslec BM-S, manufactured by Sekisui Chemical Co., Ltd.) were mixed with 10 parts of methyl isobutyl ketone.
The mixture was mixed with glass beads (manufactured by Shinmaru Enterprises, Hybee D-20) for 4 hours using a paint conditioner. The pigment dispersion thus obtained is applied to an aluminum plate (JI) using an applicator.
(S Standard # 1050) and dried at 80 ° C. for 15 minutes to obtain a charge generation layer having a thickness of about 0.2 μm.

【０１５４】次に例示化合物（ＣＴ２−６）で示される
電荷移動剤１０重量部と例示化合物（ＣＰ−１）で示さ
れる共重合体化合物（重量平均分子量；３１０００）１
０重量部とＤＬ−α−トコフェロール０．１重量部をジ
クロロメタン１５０重量部に溶解させて、上記電荷発生
層の上に、この溶液をアプリケーターにより塗布し、８
０℃で６０分乾燥して乾燥膜厚２０μｍの電荷移動層を
形成した。Next, 10 parts by weight of a charge transfer agent represented by Exemplified Compound (CT2-6) and a copolymer compound represented by Exemplified Compound (CP-1) (weight average molecular weight: 31000) 1
0 parts by weight and 0.1 parts by weight of DL-α-tocopherol are dissolved in 150 parts by weight of dichloromethane, and this solution is applied on the above-mentioned charge generating layer by an applicator.
After drying at 0 ° C. for 60 minutes, a charge transfer layer having a dry film thickness of 20 μm was formed.

【０１５５】この様にして作製した積層型電子写真感光
体を室温暗中に一昼夜保管した後、静電記録試験装置
（川口電機製作所製、ＳＰ−４２８）により電子写真特
性評価を行った。測定条件は、コロナ印加電圧：−５．
０ｋＶ、スタティックモードＮｏ．３（プロセス速度１
６７ｍｍ／ｓ）、照射光（白色光）照度：２ｌｘであっ
た。その結果、帯電電位−７２０Ｖ、半減露光量１．１
ｌｘ・ｓと非常に高感度の値を示した。結果を表１５に
示す。After storing the laminated electrophotographic photoreceptor thus produced in the dark at room temperature for 24 hours, the electrophotographic characteristics were evaluated using an electrostatic recording tester (SP-428, manufactured by Kawaguchi Electric Works). The measurement conditions were as follows: Corona applied voltage: -5.
0 kV, static mode No. 3 (Process speed 1
67 mm / s) and irradiation light (white light) illuminance: 2 lx. As a result, the charging potential was -720 V, the half-exposure amount was 1.1
It showed a very high sensitivity value of lx · s. Table 15 shows the results.

【０１５６】次に、この感光体をアルミニウム製のドラ
ム素管に張り付け、ドラム感光体評価装置（ジェンテッ
ク製、シンシア９０）により帯電及び光除電の繰り返し
特性を評価した。測定は、コロナ印加電圧：−５．２ｋ
Ｖ、プロセス速度１６０ｍｍ／ｓ、ＴＣＣＤ２モードで
の５０００回の帯電及び光除電の繰り返しを行った。光
除電はタングステンランプアレイを用いて行った。帯電
後の表面電位即ち帯電電位、光除電後の表面電位即ち残
留電位の測定結果を表１５に示す。帯電電位及び残留電
位の変化が極めて小さいことがわかる。Next, this photoreceptor was attached to an aluminum drum tube, and the repetition characteristics of charging and light elimination were evaluated by a drum photoreceptor evaluation device (Gentech, Cynthia 90). The measurement was performed with a corona applied voltage of -5.2 k.
V, the process speed was 160 mm / s, and the charge and light elimination were repeated 5000 times in TCCD2 mode. Light elimination was performed using a tungsten lamp array. Table 15 shows the measurement results of the surface potential after charging, that is, the charging potential, and the surface potential after light removal, that is, the residual potential. It can be seen that changes in the charging potential and the residual potential are extremely small.

【０１５７】また、同様にして作製した感光体の摩耗量
をスガ摩耗試験機を用いて測定した。測定条件は、粗さ
２０００番のサンドペーパーを使用し、加重４００ｇ、
繰り返し回数３００回で行った。感光体の耐摩耗性につ
いては、摩耗量＜１．９ｍｇを◎、１．９ｍｇ≦摩耗量
＜２．２ｍｇを○、２．２ｍｇ≦摩耗量＜２．５ｍｇを
△、２．５ｍｇ≦摩耗量、という基準で評価した。結果
を表１６に示す。Further, the abrasion loss of the photosensitive member produced in the same manner was measured using a Suga abrasion tester. The measurement conditions were as follows: using a sandpaper with a roughness of 2000, weight 400g,
The test was repeated 300 times. Regarding the abrasion resistance of the photoreceptor, abrasion amount <1.9 mg, ◎ 1.9 mg ≦ abrasion amount <2.2 mg, o, 2.2 mg ≦ abrasion amount <2.5 mg, Δ, 2.5 mg ≦ abrasion amount The evaluation was based on the following criteria. Table 16 shows the results.

【０１５８】実施例１２ 実施例１１において、例示化合物（ＣＴ２−６）で表さ
れる電荷移動剤の代わりに、例示化合物（ＣＴ２−９）
を用いた以外は実施例１１と同様にして電子写真感光体
を作製し、実施例１１と同様の試験を行った。Example 12 In Example 11, the compound (CT2-9) was used instead of the charge transfer agent represented by the compound (CT2-6).
An electrophotographic photoreceptor was prepared in the same manner as in Example 11 except for using, and the same test as in Example 11 was performed.

【０１５９】実施例１３ 実施例１１において、例示化合物（ＣＴ２−６）で表さ
れる電荷移動剤の代わりに、例示化合物（ＣＴ２−１
２）を用い、例示化合物（ＣＰ−１）で表される共重合
体化合物の代わりに、例示化合物（ＣＰ−２）（重量平
均分子量；３２０００）を用いた以外は実施例１１と同
様にして電子写真感光体を作製し、実施例１１と同様の
試験を行った。Example 13 In Example 11, instead of the charge transfer agent represented by the exemplified compound (CT2-6), the exemplified compound (CT2-1) was used.
Example 11 was repeated in the same manner as in Example 11, except that Example Compound (CP-2) (weight average molecular weight; 32,000) was used in place of the copolymer compound represented by Example Compound (CP-1). An electrophotographic photoreceptor was manufactured, and the same test as in Example 11 was performed.

【０１６０】実施例１４ 実施例１１において、例示化合物（ＣＴ２−６）で表さ
れる電荷移動剤の代わりに、例示化合物（ＣＴ２−１
８）を用い、例示化合物（ＣＰ−１）で表される共重合
体化合物の代わりに、例示化合物（ＣＰ−２）を用いた
以外は実施例１１と同様にして電子写真感光体を作製
し、実施例１１と同様の試験を行った。Example 14 In Example 11, instead of the charge transfer agent represented by the exemplified compound (CT2-6), the exemplified compound (CT2-1) was used.
8), and an electrophotographic photosensitive member was prepared in the same manner as in Example 11 except that Exemplified Compound (CP-2) was used instead of the copolymer compound represented by Exemplified Compound (CP-1). The same test as in Example 11 was performed.

【０１６１】実施例１５ 実施例１１において、例示化合物（ＣＧ−８）で表され
る電荷発生剤の代わりに、例示化合物（ＣＧ−２７）を
用い、例示化合物（ＣＴ２−６）で表される電荷移動剤
の代わりに、例示化合物（ＣＴ２−２１）を用い、例示
化合物（ＣＰ−１）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−６）（重量平均分子量；３３０
００）を用いた以外は実施例１１と同様にして電子写真
感光体を作製し、実施例１１と同様の試験を行った。Example 15 In Example 11, Exemplified Compound (CT2-6) was used instead of the charge generating agent represented by Exemplified Compound (CG-8). Instead of the charge transfer agent, the exemplary compound (CT2-21) is used, and instead of the copolymer compound represented by the exemplary compound (CP-1), the exemplary compound (CP-6) (weight average molecular weight; 330)
An electrophotographic photosensitive member was prepared in the same manner as in Example 11 except that (00) was used, and the same test as in Example 11 was performed.

【０１６２】実施例１６ 実施例１１において、例示化合物（ＣＧ−８）で表され
る電荷発生剤の代わりに、例示化合物（ＣＧ−２７）を
用い、例示化合物（ＣＴ２−６）で表される電荷移動剤
の代わりに、例示化合物（ＣＴ２−２８）を用い、例示
化合物（ＣＰ−１）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−１０）（重量平均分子量；３５
０００）を用いた以外は実施例１１と同様にして電子写
真感光体を作製し、実施例１１と同様の試験を行った。Example 16 The procedure of Example 11 was repeated, except that the charge generating agent represented by the exemplified compound (CG-8) was replaced by the exemplified compound (CG-27). Instead of the charge transfer agent, the exemplary compound (CT2-28) is used, and instead of the copolymer compound represented by the exemplary compound (CP-1), the exemplary compound (CP-10) (weight average molecular weight; 35)
000), an electrophotographic photosensitive member was prepared in the same manner as in Example 11, and the same test as in Example 11 was performed.

【０１６３】実施例１７ 実施例１１において、例示化合物（ＣＧ−８）で表され
る電荷発生剤の代わりに、例示化合物（ＣＧ−２７）を
用い、例示化合物（ＣＴ２−６）で表される電荷移動剤
の代わりに、例示化合物（ＣＴ２−９）を用い、例示化
合物（ＣＰ−１）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−５３）（重量平均分子量；３４
０００）を用いた以外は実施例１１と同様にして電子写
真感光体を作製し、実施例１１と同様の試験を行った。Example 17 In Example 11, an exemplified compound (CT2-6) was used instead of the charge generating agent represented by the exemplified compound (CG-8), except that the exemplified compound (CG-27) was used. Instead of the charge transfer agent, the exemplary compound (CT2-9) is used, and instead of the copolymer compound represented by the exemplary compound (CP-1), the exemplary compound (CP-53) (weight average molecular weight; 34)
000), an electrophotographic photosensitive member was prepared in the same manner as in Example 11, and the same test as in Example 11 was performed.

【０１６４】実施例１８ 実施例１１において、例示化合物（ＣＧ−８）で表され
る電荷発生剤の代わりに、例示化合物（ＣＧ−３４）を
用い、例示化合物（ＣＴ２−６）で表される電荷移動剤
の代わりに、例示化合物（ＣＴ２−３９）を用い、例示
化合物（ＣＰ−１）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−５６）（重量平均分子量；２４
０００）を用いた以外は実施例１１と同様にして電子写
真感光体を作製し、実施例１１と同様の試験を行った。Example 18 In Example 11, an exemplified compound (CT2-6) was used instead of the charge generating agent represented by the exemplified compound (CG-8), except that the exemplified compound (CG-34) was used. Instead of the charge transfer agent, the exemplary compound (CT2-39) was used, and instead of the copolymer compound represented by the exemplary compound (CP-1), the exemplary compound (CP-56) (weight average molecular weight; 24)
000), an electrophotographic photosensitive member was prepared in the same manner as in Example 11, and the same test as in Example 11 was performed.

【０１６５】実施例１９ 実施例１１において、例示化合物（ＣＧ−８）で表され
る電荷発生剤の代わりに、例示化合物（ＣＧ−３４）を
用い、例示化合物（ＣＴ２−６）で表される電荷移動剤
の代わりに、例示化合物（ＣＴ２−４２）を用い、例示
化合物（ＣＰ−１）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−３）（重量平均分子量；３００
００）を用いた以外は実施例１１と同様にして電子写真
感光体を作製し、実施例１１と同様の試験を行った。Example 19 The procedure of Example 11 was repeated, except that the charge generating agent represented by the exemplified compound (CG-8) was replaced by the exemplified compound (CG-34). Instead of the charge transfer agent, the exemplary compound (CT2-42) is used, and instead of the copolymer compound represented by the exemplary compound (CP-1), the exemplary compound (CP-3) (weight average molecular weight: 300)
An electrophotographic photosensitive member was prepared in the same manner as in Example 11 except that (00) was used, and the same test as in Example 11 was performed.

【０１６６】実施例２０ 実施例１１において、例示化合物（ＣＧ−８）で表され
る電荷発生剤の代わりに、下記例示化合物（ＣＧ−４
６）を用いた以外は実施例１１と同様にして電子写真感
光体を作製し、実施例１１と同様の試験を行った。Example 20 In Example 11, the following exemplified compound (CG-4) was used in place of the charge generating agent represented by the exemplified compound (CG-8).
An electrophotographic photosensitive member was prepared in the same manner as in Example 11 except that 6) was used, and the same test as in Example 11 was performed.

【０１６７】[0167]

【化７１】 Embedded image

【０１６８】比較例６ 実施例１１において、例示化合物（ＣＰ−１）で表され
る共重合体化合物の代わりに、ポリスチレン樹脂（旭化
成製、スタイロン６８５）を用いた以外は実施例１１と
同様にして電子写真感光体を作製し、実施例１１と同様
の試験を行った。Comparative Example 6 The procedure of Example 11 was repeated, except that a polystyrene resin (Stylon 685, manufactured by Asahi Kasei) was used instead of the copolymer compound represented by the exemplified compound (CP-1). Thus, an electrophotographic photosensitive member was manufactured, and the same test as in Example 11 was performed.

【０１６９】比較例７ 実施例１３において、例示化合物（ＣＰ−２）で表され
る共重合体化合物の代わりに、ポリカーボネート樹脂
（帝人化成製、パンライトＬ−１２２５）を用いた以外
は実施例１３と同様にして電子写真感光体を作製し、実
施例１３と同様の試験を行った。Comparative Example 7 The procedure of Example 13 was repeated except that a polycarbonate resin (manufactured by Teijin Chemicals Ltd., Panlite L-1225) was used instead of the copolymer compound represented by the exemplified compound (CP-2). An electrophotographic photosensitive member was produced in the same manner as in Example 13, and the same test as in Example 13 was performed.

【０１７０】比較例８ 実施例１５において、例示化合物（ＣＰ−６）で表され
る共重合体化合物の代わりに、ポリアリレート樹脂（ユ
ニチカ製、Ｕ−１００Ｄ）を用いた以外は実施例１５と
同様にして電子写真感光体を作製し、実施例１５と同様
の試験を行った。Comparative Example 8 The procedure of Example 15 was repeated, except that a polyarylate resin (U-100D, manufactured by Unitika) was used in place of the copolymer compound represented by the exemplified compound (CP-6). In the same manner, an electrophotographic photosensitive member was manufactured, and the same test as in Example 15 was performed.

【０１７１】比較例９ 実施例１８において、例示化合物（ＣＴ２−３９）で表
される電荷移動剤の代わりに、比較化合物（ＥＸ−２）
を用いた以外は実施例１８と同様にして電子写真感光体
を作製し、実施例１８と同様の試験を行った。Comparative Example 9 In Example 18, the charge transfer agent represented by the exemplified compound (CT2-39) was replaced with the comparative compound (EX-2)
An electrophotographic photoreceptor was prepared in the same manner as in Example 18 except for using, and the same test as in Example 18 was performed.

【０１７２】比較例１０ 実施例１９において、例示化合物（ＣＴ２−４２）で表
される電荷移動剤の代わりに、比較化合物（ＥＸ−３）
を用いた以外は実施例１９と同様にして電子写真感光体
を作製し、実施例１９と同様の試験を行った。Comparative Example 10 In Example 19, a comparative compound (EX-3) was used in place of the charge transfer agent represented by the exemplified compound (CT2-42).
An electrophotographic photoreceptor was prepared in the same manner as in Example 19, except that was used, and the same test as in Example 19 was performed.

【０１７３】実施例１１から２０までの電気特性の結果
をを表１５に示し、耐摩耗性試験の結果を表１６に示
す。また、比較例６から１０までの電気特性の結果を表
１７に示し、耐摩耗性の結果を表１８に示す。Table 15 shows the results of the electrical characteristics of Examples 11 to 20, and Table 16 shows the results of the wear resistance test. Table 17 shows the results of the electrical characteristics of Comparative Examples 6 to 10, and Table 18 shows the results of the wear resistance.

【０１７４】[0174]

【表１５】 [Table 15]

【０１７５】[0175]

【表１６】 [Table 16]

【０１７６】[0176]

【表１７】 [Table 17]

【０１７７】[0177]

【表１８】 [Table 18]

【０１７８】上記のように、実施例１１から２０で例示
した感光体は、高感度で繰り返し安定性に優れ、かつ耐
摩耗性に優れているが、実施例２０では感度及び繰り返
し安定性が、実施例１１から１９に比べるとやや劣って
いる。一方、比較例６から１０で例示した感光体は、全
体的に低感度で繰り返し安定性に劣り、耐摩耗性も劣っ
ている。比較例９、１０は耐摩耗性の面ではそれほど劣
っていないが、感度及び繰り返し安定性が劣っている。
このように繰り返し安定性が劣っていると、コピー実写
評価では、繰り返しにより実写画像のコントラストが低
下すると共にカブリが発生する。As described above, the photoconductors exemplified in Examples 11 to 20 have high sensitivity, excellent repetition stability, and excellent abrasion resistance. In Example 20, however, the sensitivity and the repetition stability are low. It is slightly inferior to Examples 11 to 19. On the other hand, the photoconductors exemplified in Comparative Examples 6 to 10 are generally low in sensitivity, inferior in repetition stability, and inferior in wear resistance. Comparative Examples 9 and 10 are not so inferior in terms of wear resistance, but are inferior in sensitivity and repetition stability.
If the repetition stability is inferior as described above, in the actual copy image evaluation, the repetition lowers the contrast of the actual image and causes fogging.

【０１７９】実施例２１ 例示化合物（ＣＧ−１０）で示される電荷発生剤１重量
部とポリビニルブチラール樹脂（積水化学工業製、エス
レックＫＳ−１）１重量部をメチルエチルケトン１００
重量部に混合し、ペイントコンディショナーによりガラ
スビーズ（シンマルエンタープライゼズ製、ハイビーＤ
−２０）と共に４時間分散した。こうして得た顔料分散
液をアプリケーターにて金属アルミニウム薄板（ＪＩＳ
規格＃１０５０）上に塗布し、８０℃で１５分乾燥して
膜厚約０．２μｍの電荷発生層を得た。Example 21 1 part by weight of a charge generating agent represented by the exemplified compound (CG-10) and 1 part by weight of a polyvinyl butyral resin (Eslek KS-1 manufactured by Sekisui Chemical Co., Ltd.) were mixed with 100 parts of methyl ethyl ketone.
Parts by weight and mixed with glass beads (Shinmaru Enterprises, Hibee D) by a paint conditioner.
-20) and dispersed for 4 hours. The pigment dispersion thus obtained is applied to a metal aluminum sheet (JIS) using an applicator.
Standard # 1050) and dried at 80 ° C. for 15 minutes to obtain a charge generation layer having a thickness of about 0.2 μm.

【０１８０】次に例示化合物（ＣＴ３−１）で示される
電荷移動剤１０重量部と例示化合物（ＣＰ−２）で示さ
れる共重合体化合物（重量平均分子量；３２０００）１
０重量部とＤＬ−α−トコフェロール０．１重量部をジ
クロロメタン１５０重量部に溶解させて、上記電荷発生
層の上に、この溶液をアプリケーターにより塗布し、８
０℃で６０分乾燥して乾燥膜厚２０μｍの電荷移動層を
形成した。Next, 10 parts by weight of a charge transfer agent represented by Exemplified Compound (CT3-1) and a copolymer compound represented by Exemplified Compound (CP-2) (weight average molecular weight: 32000) 1
0 parts by weight and 0.1 parts by weight of DL-α-tocopherol are dissolved in 150 parts by weight of dichloromethane, and this solution is applied on the above-mentioned charge generating layer by an applicator.
After drying at 0 ° C. for 60 minutes, a charge transfer layer having a dry film thickness of 20 μm was formed.

【０１８１】この様にして作製した積層型電子写真感光
体を室温暗中に一昼夜保管した後、静電記録試験装置
（川口電機製作所製、ＳＰ−４２８）により電子写真特
性評価を行った。測定条件は、コロナ印加電圧：−５ｋ
Ｖ、スタティックモードＮｏ．３（プロセス速度１６７
ｍｍ／ｓ）、照射光（白色光）照度：２ｌｘであった。
その結果、帯電電位−７１５Ｖ、半減露光量１．１ｌｘ
・ｓと非常に高感度の値を示した。結果を表１９に示
す。After the laminated electrophotographic photosensitive member thus produced was stored in the dark at room temperature for 24 hours, the electrophotographic characteristics were evaluated by an electrostatic recording tester (SP-428, manufactured by Kawaguchi Electric Works). The measurement conditions were as follows: Corona applied voltage: -5k
V, static mode No. 3 (process speed 167
mm / s) and irradiation light (white light) illuminance: 2 lx.
As a result, the charging potential was -715 V, the half-reduction exposure amount was 1.1 lx.
・ The value of s was very high. The results are shown in Table 19.

【０１８２】次に、この感光体をアルミニウム製のドラ
ム素管に張り付け、ドラム感光体評価装置（ジェンテッ
ク製、シンシア９０）により帯電及び光除電の繰り返し
特性を評価した。測定は、コロナ印加電圧：−５．２ｋ
Ｖ、プロセス速度１６０ｍｍ／ｓ、ＴＣＣＤ２モードで
の５０００回の帯電及び光除電の繰り返しを行った。光
除電はタングステンランプアレイを用いて行った。帯電
後の表面電位即ち帯電電位、光除電後の表面電位即ち残
留電位の測定結果を表１９に示す。帯電電位及び残留電
位の変化が極めて小さいことがわかる。Next, this photoreceptor was attached to a drum tube made of aluminum, and the repetition characteristics of charging and light elimination were evaluated by a drum photoreceptor evaluation device (Gentech, Cynthia 90). The measurement was performed with a corona applied voltage of -5.2 k.
V, the process speed was 160 mm / s, and the charge and light elimination were repeated 5000 times in TCCD2 mode. Light elimination was performed using a tungsten lamp array. Table 19 shows the measurement results of the surface potential after charging, that is, the charging potential, and the surface potential after light removal, that is, the residual potential. It can be seen that changes in the charging potential and the residual potential are extremely small.

【０１８３】また、同様にして作製した感光体の摩耗量
をスガ摩耗試験機を用いて測定した。測定条件は、粗さ
２０００番のサンドペーパーを使用し、加重４００ｇ、
繰り返し回数３００回で行った。感光体の耐摩耗性につ
いては、摩耗量＜１．９ｍｇを◎、１．９ｍｇ≦摩耗量
＜２．２ｍｇを○、２．２ｍｇ≦摩耗量＜２．５ｍｇを
△、２．５ｍｇ≦摩耗量、という基準で評価した。結果
を表２０に示す。Further, the abrasion loss of the photoreceptor produced in the same manner was measured using a Suga abrasion tester. The measurement conditions were as follows: using a sandpaper with a roughness of 2000, weight 400g,
The test was repeated 300 times. Regarding the abrasion resistance of the photoreceptor, abrasion amount <1.9 mg, ◎ 1.9 mg ≦ abrasion amount <2.2 mg, o, 2.2 mg ≦ abrasion amount <2.5 mg, Δ, 2.5 mg ≦ abrasion amount The evaluation was based on the following criteria. The results are shown in Table 20.

【０１８４】実施例２２ 実施例２１において、例示化合物（ＣＴ３−１）で表さ
れる電荷移動剤の代わりに、例示化合物（ＣＴ３−２）
を用いた以外は実施例２１と同様にして電子写真感光体
を作製し、実施例２１と同様の試験を行った。Example 22 In Example 21, the compound (CT3-2) was used in place of the charge transfer agent represented by the compound (CT3-1).
An electrophotographic photoreceptor was prepared in the same manner as in Example 21 except for using, and the same test as in Example 21 was performed.

【０１８５】実施例２３ 実施例１１において、例示化合物（ＣＴ３−１）で表さ
れる電荷移動剤の代わりに、例示化合物（ＣＴ３−１
５）を用い、例示化合物（ＣＰ−２）で表される共重合
体化合物の代わりに、例示化合物（ＣＰ−４）（重量平
均分子量；３１０００）を用いた以外は実施例２１と同
様にして電子写真感光体を作製し、実施例２１と同様の
試験を行った。Example 23 In Example 11, instead of the charge transfer agent represented by the exemplified compound (CT3-1), the exemplified compound (CT3-1) was used.
Example 21 was repeated in the same manner as in Example 21 except that Example Compound (CP-4) (weight average molecular weight: 31000) was used in place of the copolymer compound represented by Example Compound (CP-2). An electrophotographic photoreceptor was manufactured, and the same test as in Example 21 was performed.

【０１８６】実施例２４ 実施例２１において、例示化合物（ＣＴ３−１）で表さ
れる電荷移動剤の代わりに、例示化合物（ＣＴ３−７）
を用い、例示化合物（ＣＰ−２）で表される共重合体化
合物の代わりに、例示化合物（ＣＰ−４）（重量平均分
子量；３１０００）を用いた以外は実施例２１と同様に
して電子写真感光体を作製し、実施例２１と同様の試験
を行った。Example 24 In Example 21, the compound (CT3-7) was used in place of the charge transfer agent represented by the compound (CT3-1).
And the electrophotography was performed in the same manner as in Example 21 except that Exemplified Compound (CP-4) (weight average molecular weight; 31000) was used instead of the copolymer compound represented by Exemplified Compound (CP-2). A photoreceptor was manufactured and the same test as in Example 21 was performed.

【０１８７】実施例２５ 実施例２１において、例示化合物（ＣＧ−１０）で表さ
れる電荷発生剤の代わりに、例示化合物（ＣＧ−２９）
を用い、例示化合物（ＣＴ３−１）で表される電荷移動
剤の代わりに、例示化合物（ＣＴ３−１０）を用い、例
示化合物（ＣＰ−２）で表される共重合体化合物の代わ
りに、例示化合物（ＣＰ−１０）（重量平均分子量；３
５０００）を用いた以外は実施例２１と同様にして電子
写真感光体を作製し、実施例２１と同様の試験を行っ
た。Example 25 In Example 21, the compound (CG-29) was used in place of the charge generator represented by the compound (CG-10).
And using the exemplary compound (CT3-10) instead of the charge transfer agent represented by the exemplary compound (CT3-1) and replacing the copolymer compound represented by the exemplary compound (CP-2) by Exemplified compound (CP-10) (weight average molecular weight; 3)
An electrophotographic photoreceptor was produced in the same manner as in Example 21 except for using (5000), and the same test as in Example 21 was conducted.

【０１８８】実施例２６ 実施例２１において、例示化合物（ＣＧ−１０）で表さ
れる電荷発生剤の代わりに、例示化合物（ＣＧ−２９）
を用い、例示化合物（ＣＴ３−１）で表される電荷移動
剤の代わりに、例示化合物（ＣＴ３−１３）を用い、例
示化合物（ＣＰ−２）で表される共重合体化合物の代わ
りに、例示化合物（ＣＰ−１）（重量平均分子量３１０
００）を用いた以外は実施例２１と同様にして電子写真
感光体を作製し、実施例２１と同様の試験を行った。Example 26 In Example 21, the compound (CG-29) was replaced with the charge generating agent represented by the compound (CG-10).
And using the exemplified compound (CT3-13) instead of the charge transfer agent represented by the exemplified compound (CT3-1) and replacing the copolymer compound represented by the exemplified compound (CP-2) with: Exemplified compound (CP-1) (weight average molecular weight 310
An electrophotographic photosensitive member was prepared in the same manner as in Example 21 except that (00) was used, and the same test as in Example 21 was performed.

【０１８９】実施例２７ 実施例２１において、例示化合物（ＣＧ−１０）で表さ
れる電荷発生剤の代わりに、例示化合物（ＣＧ−２９）
を用い、例示化合物（ＣＴ３−１）で表される電荷移動
剤の代わりに、例示化合物（ＣＴ３−７）を用い、例示
化合物（ＣＰ−２）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−２１）（重量平均分子量；３４
０００）を用いた以外は実施例２１と同様にして電子写
真感光体を作製し、実施例２１と同様の試験を行った。Example 27 In Example 21, the compound (CG-29) was used in place of the charge generator represented by the compound (CG-10).
And using the exemplary compound (CT3-7) instead of the charge transfer agent represented by the exemplary compound (CT3-1) and replacing the copolymer compound represented by the exemplary compound (CP-2) by Exemplified compound (CP-21) (weight average molecular weight; 34)
000), an electrophotographic photosensitive member was produced in the same manner as in Example 21, and the same test as in Example 21 was conducted.

【０１９０】実施例２８ 実施例２１において、例示化合物（ＣＧ−１０）で表さ
れる電荷発生剤の代わりに、例示化合物（ＣＧ−３６）
を用い、例示化合物（ＣＴ３−１）で表される電荷移動
剤の代わりに、例示化合物（ＣＴ３−２）を用い、例示
化合物（ＣＰ−２）で表される共重合体化合物の代わり
に、例示化合物（ＣＰ−１８）（重量平均分子量；４２
０００）を用いた以外は実施例２１と同様にして電子写
真感光体を作製し、実施例２１と同様の試験を行った。Example 28 In Example 21, the compound (CG-36) was used instead of the charge generating agent represented by the compound (CG-10).
And using the exemplary compound (CT3-2) instead of the charge transfer agent represented by the exemplary compound (CT3-1) and replacing the copolymer compound represented by the exemplary compound (CP-2) with: Exemplified compound (CP-18) (weight average molecular weight; 42)
000), an electrophotographic photosensitive member was produced in the same manner as in Example 21, and the same test as in Example 21 was conducted.

【０１９１】実施例２９ 実施例２１において、例示化合物（ＣＧ−１０）で表さ
れる電荷発生剤の代わりに、例示化合物（ＣＧ−３６）
を用い、例示化合物（ＣＴ３−１）で表される電荷移動
剤の代わりに、例示化合物（ＣＴ３−１０）を用い、例
示化合物（ＣＰ−２）で表される共重合体化合物の代わ
りに、例示化合物（ＣＰ−２７）（重量平均分子量；２
２０００）を用いた以外は実施例２１と同様にして電子
写真感光体を作製し、実施例２１と同様の試験を行っ
た。Example 29 In Example 21, the compound (CG-36) was used instead of the charge generating agent represented by the compound (CG-10).
And using the exemplary compound (CT3-10) instead of the charge transfer agent represented by the exemplary compound (CT3-1) and replacing the copolymer compound represented by the exemplary compound (CP-2) by Exemplified compound (CP-27) (weight average molecular weight; 2)
An electrophotographic photoreceptor was prepared in the same manner as in Example 21 except that the method of Example 21 was used, and the same test as in Example 21 was performed.

【０１９２】実施例３０ 実施例２１において、例示化合物（ＣＧ−１０）で表さ
れる電荷発生剤の代わりに、下記例示化合物（ＣＧ−４
７）を用いた以外は実施例２１と同様にして電子写真感
光体を作製し、実施例２１と同様の試験を行った。Example 30 In Example 21, the following exemplified compound (CG-4) was used in place of the charge generating agent represented by the exemplified compound (CG-10).
An electrophotographic photosensitive member was prepared in the same manner as in Example 21 except that 7) was used, and the same test as in Example 21 was performed.

【０１９３】[0193]

【化７２】 Embedded image

【０１９４】比較例１１ 実施例２１において、例示化合物（ＣＰ−２）で表され
る共重合体化合物の代わりに、ポリエステル樹脂（東洋
紡製、バイロン２００）を用いた以外は実施例２１と同
様にして電子写真感光体を作製し、実施例２１と同様の
試験を行った。Comparative Example 11 The procedure of Example 21 was repeated, except that a polyester resin (manufactured by Toyobo, Byron 200) was used instead of the copolymer compound represented by the exemplified compound (CP-2). Thus, an electrophotographic photosensitive member was manufactured, and the same test as in Example 21 was performed.

【０１９５】比較例１２ 実施例２４において、例示化合物（ＣＰ−４）で表され
る共重合体化合物の代わりに、ポリカーボネート樹脂
（帝人化成製、パンライトＬ−１２５０）を用いた以外
は実施例２４と同様にして電子写真感光体を作製し、実
施例２４と同様の試験を行った。Comparative Example 12 The procedure of Example 24 was repeated except that a polycarbonate resin (manufactured by Teijin Chemicals Ltd., Panlite L-1250) was used instead of the copolymer compound represented by the exemplified compound (CP-4). An electrophotographic photosensitive member was prepared in the same manner as in Example 24, and the same test as in Example 24 was performed.

【０１９６】比較例１３ 実施例２６において、例示化合物（ＣＰ−１）で表され
る共重合体化合物の代わりに、ポリスチレン樹脂（旭化
成製、スタイロン６６６）を用いた以外は実施例２６と
同様にして電子写真感光体を作製し、実施例２６と同様
の試験を行った。Comparative Example 13 The procedure of Example 26 was repeated, except that a polystyrene resin (Stylon 666, manufactured by Asahi Kasei) was used in place of the copolymer compound represented by the exemplified compound (CP-1). Thus, an electrophotographic photosensitive member was manufactured, and the same test as in Example 26 was performed.

【０１９７】比較例１４ 実施例２８において、例示化合物（ＣＴ３−２）で表さ
れる電荷移動剤の代わりに、比較化合物（ＥＸ−３）を
用いた以外は実施例２８と同様にして電子写真感光体を
作製し、実施例２８と同様の試験を行った。Comparative Example 14 An electrophotograph was prepared in the same manner as in Example 28 except that the comparative compound (EX-3) was used in place of the charge transfer agent represented by the exemplified compound (CT3-2). A photoconductor was prepared, and the same test as in Example 28 was performed.

【０１９８】比較例１５ 実施例２９において、例示化合物（ＣＴ３−１０）で表
される電荷移動剤の代わりに、比較化合物（ＥＸ−１）
を用いた以外は実施例２９と同様にして電子写真感光体
を作製し、実施例２９と同様の試験を行った。Comparative Example 15 In Example 29, a comparative compound (EX-1) was used in place of the charge transfer agent represented by the exemplified compound (CT3-10).
An electrophotographic photoreceptor was prepared in the same manner as in Example 29, except that was used, and the same test as in Example 29 was performed.

【０１９９】実施例２１から３０までの電気特性の結果
をを表１９に示し、耐摩耗性試験の結果を表２０に示
す。また、比較例１１から１５までの電気特性の結果を
表２１に示し、耐摩耗性の結果を表２２に示す。The results of the electrical characteristics of Examples 21 to 30 are shown in Table 19, and the results of the wear resistance test are shown in Table 20. Table 21 shows the results of the electrical characteristics of Comparative Examples 11 to 15, and Table 22 shows the results of the abrasion resistance.

【０２００】[0200]

【表１９】 [Table 19]

【０２０１】[0201]

【表２０】 [Table 20]

【０２０２】[0202]

【表２１】 [Table 21]

【０２０３】[0203]

【表２２】 [Table 22]

【０２０４】上記のように、実施例２１から３０で例示
した感光体は、高感度で繰り返し安定性に優れ、かつ耐
摩耗性に優れているが、実施例３０では感度及び繰り返
し安定性が、実施例２１から２９と比べるとやや劣って
いる。一方、比較例１１から１５で例示した感光体は、
全体的に低感度で繰り返し安定性に劣り、耐摩耗性も劣
っている。比較例１４、１５は耐摩耗性の面ではそれほ
ど劣っていないが、感度及び繰り返し安定性が劣ってい
る。このように繰り返し安定性が劣っていると、コピー
実写評価では、繰り返しにより実写画像のコントラスト
が低下すると共にカブリが発生する。As described above, the photoconductors exemplified in Examples 21 to 30 have high sensitivity, excellent repetition stability, and excellent abrasion resistance. In Example 30, however, the sensitivity and the repetition stability are low. It is slightly inferior to Examples 21 to 29. On the other hand, the photoconductors exemplified in Comparative Examples 11 to 15 are:
Overall, the sensitivity is low, the repetition stability is inferior, and the abrasion resistance is inferior. Comparative Examples 14 and 15 are not so inferior in terms of wear resistance, but are inferior in sensitivity and repetition stability. If the repetition stability is inferior as described above, in the actual copy image evaluation, the repetition lowers the contrast of the actual image and causes fogging.

【０２０５】実施例３１ 電荷発生剤としてτ型無金属フタロシアニン（東洋イン
キ製造製、ＴＰＡ−８９１）１重量部と塩化ビニル−酢
酸ビニル共重合樹脂（積水化学工業製、エスレックＣ）
１重量部を酢酸ブチル１００重量部に混合し、ペイント
コンディショナーによりガラスビーズ（シンマルエンタ
ープライゼズ製、ハイビーＤ−２０）と共に４時間分散
した。こうして得た顔料分散液をアプリケーターにて金
属アルミニウム薄板（ＪＩＳ規格＃１０５０）上に塗布
し、８０℃で１５分乾燥して膜厚約０．２μｍの電荷発
生層を得た。Example 31 1 part by weight of a τ-type metal-free phthalocyanine (TPA-891, manufactured by Toyo Ink Manufacturing Co., Ltd.) as a charge generating agent and a vinyl chloride-vinyl acetate copolymer resin (Eslek C, manufactured by Sekisui Chemical Co., Ltd.)
One part by weight was mixed with 100 parts by weight of butyl acetate, and dispersed together with glass beads (manufactured by Shinmaru Enterprises, Hybee D-20) for 4 hours using a paint conditioner. The pigment dispersion thus obtained was applied on a metal aluminum sheet (JIS standard # 1050) using an applicator, and dried at 80 ° C. for 15 minutes to obtain a charge generation layer having a thickness of about 0.2 μm.

【０２０６】次に例示化合物（ＣＴ１−１３）で示され
る電荷移動剤１０重量部と例示化合物（ＣＰ−２）で示
される共重合体化合物（重量平均分子量；３２０００）
１０重量部をジクロロメタン１５０重量部に溶解させ
て、上記電荷発生層の上に、この溶液をアプリケーター
により塗布し、８０℃で６０分乾燥して乾燥膜厚２０μ
ｍの電荷移動層を形成した。Next, 10 parts by weight of a charge transfer agent represented by the exemplified compound (CT1-13) and a copolymer compound represented by the exemplified compound (CP-2) (weight average molecular weight: 32,000)
10 parts by weight were dissolved in 150 parts by weight of dichloromethane, and this solution was applied on the charge generation layer by an applicator and dried at 80 ° C. for 60 minutes to obtain a dry film thickness of 20 μm.
m of charge transfer layers were formed.

【０２０７】この様にして作製した積層型電子写真感光
体を室温暗中に一昼夜保管した後、静電記録試験装置
（川口電機製作所製、ＳＰ−４２８）により電子写真特
性評価を行った。測定条件は、コロナ印加電圧：−５ｋ
Ｖ、スタティックモードＮｏ．３（プロセス速度１６７
ｍｍ／ｓ）、照射光（白色光）照度：２ｌｘであった。
その結果、帯電電位−６８０Ｖ、半減露光量１．２ｌｘ
・ｓと非常に高感度の値を示した。結果を表２３に示
す。After the laminated electrophotographic photoreceptor thus produced was stored in the dark at room temperature for 24 hours, electrophotographic characteristics were evaluated using an electrostatic recording tester (SP-428, manufactured by Kawaguchi Electric Works). The measurement conditions were as follows: Corona applied voltage: -5k
V, static mode No. 3 (process speed 167
mm / s) and irradiation light (white light) illuminance: 2 lx.
As a result, the charging potential was -680 V, the half-exposure amount was 1.2 lx.
・ The value of s was very high. The results are shown in Table 23.

【０２０８】次に、この感光体をアルミニウム製のドラ
ム素管に張り付け、ドラム感光体評価装置（ジェンテッ
ク製、シンシア９０）により帯電及び光除電の繰り返し
特性を評価した。測定は、コロナ印加電圧：−５．２ｋ
Ｖ、プロセス速度１６０ｍｍ／ｓ、ＴＣＣＤ２モードで
の５０００回の帯電及び光除電の繰り返しを行った。光
除電はタングステンランプアレイを用いて行った。帯電
後の表面電位即ち帯電電位、光除電後の表面電位即ち残
留電位の測定結果を表２３に示す。帯電電位及び残留電
位の変化が極めて小さいことがわかる。Next, this photoreceptor was attached to a drum tube made of aluminum, and the repetition characteristics of charging and light elimination were evaluated using a drum photoreceptor evaluation device (Gentech, Cynthia 90). The measurement was performed with a corona applied voltage of -5.2 k.
V, the process speed was 160 mm / s, and the charge and light elimination were repeated 5000 times in TCCD2 mode. Light elimination was performed using a tungsten lamp array. Table 23 shows the measurement results of the surface potential after charging, that is, the charging potential, and the surface potential after light removal, that is, the residual potential. It can be seen that changes in the charging potential and the residual potential are extremely small.

【０２０９】また、同様にして作製した感光体の摩耗量
をスガ摩耗試験機を用いて測定した。測定条件は、粗さ
２０００番のサンドペーパーを使用し、加重４００ｇ、
繰り返し回数３００回で行った。感光体の耐摩耗性につ
いては、摩耗量＜１．９ｍｇを◎、１．９ｍｇ≦摩耗量
＜２．２ｍｇを○、２．２ｍｇ≦摩耗量＜２．５ｍｇを
△、２．５ｍｇ≦摩耗量、という基準で評価した。結果
を表２４に示す。Further, the abrasion loss of the photoreceptor produced in the same manner was measured using a Suga abrasion tester. The measurement conditions were as follows: using a sandpaper with a roughness of 2000, weight 400g,
The test was repeated 300 times. Regarding the abrasion resistance of the photoreceptor, abrasion amount <1.9 mg, ◎ 1.9 mg ≦ abrasion amount <2.2 mg, o, 2.2 mg ≦ abrasion amount <2.5 mg, Δ, 2.5 mg ≦ abrasion amount The evaluation was based on the following criteria. The results are shown in Table 24.

【０２１０】実施例３２ 実施例３１において、例示化合物（ＣＴ１−１３）で表
される電荷移動剤の代わりに、例示化合物（ＣＴ１−２
０）を用い、例示化合物（ＣＰ−２）で表される共重合
体化合物の代わりに、例示化合物（ＣＰ−１８）（重量
平均分子量；３６０００）を用いた以外は実施例３１と
同様にして電子写真感光体を作製し、実施例３１と同様
の試験を行った。Example 32 In Example 31, instead of the charge transfer agent represented by the exemplified compound (CT1-13), the exemplified compound (CT1-2) was used.
0), and in the same manner as in Example 31 except that the exemplary compound (CP-18) (weight average molecular weight; 36000) was used instead of the copolymer compound represented by the exemplary compound (CP-2). An electrophotographic photoreceptor was manufactured and the same test as in Example 31 was performed.

【０２１１】実施例３３ 実施例３１において、例示化合物（ＣＴ１−１３）で表
される電荷移動剤の代わりに、例示化合物（ＣＴ２−
５）を用いた以外は実施例３１と同様にして電子写真感
光体を作製し、実施例３１と同様の試験を行った。Example 33 In Example 31, instead of the charge transfer agent represented by the exemplified compound (CT1-13), the exemplified compound (CT2-
An electrophotographic photosensitive member was prepared in the same manner as in Example 31 except that 5) was used, and the same test as in Example 31 was performed.

【０２１２】実施例３４ 実施例３１において、例示化合物（ＣＴ１−１３）で表
される電荷移動剤の代わりに、例示化合物（ＣＴ２−２
１）を用い、例示化合物（ＣＰ−２）で表される共重合
体化合物の代わりに、例示化合物（ＣＰ−６）（重量平
均分子量；３３０００）を用いた以外は実施例３１と同
様にして電子写真感光体を作製し、実施例３１と同様の
試験を行った。Example 34 In Example 31, instead of the charge transfer agent represented by the exemplified compound (CT1-13), the exemplified compound (CT2-2) was used.
Example 1 was repeated in the same manner as in Example 31 except that Example Compound (CP-6) (weight average molecular weight: 33000) was used in place of the copolymer compound represented by Example Compound (CP-2). An electrophotographic photoreceptor was manufactured and the same test as in Example 31 was performed.

【０２１３】実施例３５ 実施例３１において、例示化合物（ＣＴ１−１３）で表
される電荷移動剤の代わりに、例示化合物（ＣＴ３−
４）を用い、例示化合物（ＣＰ−２）で表される共重合
体化合物の代わりに、例示化合物（ＣＰ−１）（重量平
均分子量；３１０００）を用いた以外は実施例３１と同
様にして電子写真感光体を作製し、実施例３１と同様の
試験を行った。Example 35 In Example 31, instead of the charge transfer agent represented by the exemplified compound (CT1-13), the exemplified compound (CT3-
Example 4 was repeated in the same manner as in Example 31 except that Example Compound (CP-1) (weight average molecular weight; 31000) was used instead of the copolymer compound represented by Example Compound (CP-2). An electrophotographic photoreceptor was manufactured and the same test as in Example 31 was performed.

【０２１４】実施例３６ 実施例３１において、電荷発生剤としてτ型無金属フタ
ロシアニンの代わりに、β型銅フタロシアニン（東京化
成製、一級試薬）を用いた以外は実施例３１と同様にし
て電子写真感光体を作製し、実施例３１と同様の試験を
行った。Example 36 An electrophotography was performed in the same manner as in Example 31 except that β-type copper phthalocyanine (a first-class reagent, manufactured by Tokyo Chemical Industry) was used instead of the τ-type metal-free phthalocyanine as the charge generating agent. A photoconductor was prepared, and the same test as in Example 31 was performed.

【０２１５】実施例３７ 実施例３１において、電荷発生剤としてτ型無金属フタ
ロシアニンの代わりに、オキシチタニウムフタロシアニ
ン（山陽色素製、Ｔ−２２Ｓ）を用い、例示化合物（Ｃ
Ｔ１−１３）で表される電荷移動剤の代わりに、例示化
合物（ＣＴ１−９）を用いた以外は実施例３１と同様に
して電子写真感光体を作製し、実施例３１と同様の試験
を行った。Example 37 In Example 31, oxytitanium phthalocyanine (T-22S, Sanyo Dye) was used as the charge generating agent instead of the τ-type metal-free phthalocyanine, and the compound (C) was used.
An electrophotographic photoreceptor was prepared in the same manner as in Example 31 except that the exemplified compound (CT1-9) was used instead of the charge transfer agent represented by T1-13), and a test similar to that in Example 31 was performed. went.

【０２１６】実施例３８ 実施例３１において、電荷発生剤としてτ型無金属フタ
ロシアニンの代わりに、オキシチタニウムフタロシアニ
ン（山陽色素製、Ｔ−２２Ｓ）を用い、例示化合物（Ｃ
Ｔ１−１３）で表される電荷移動剤の代わりに、例示化
合物（ＣＴ１−６）を用い、例示化合物（ＣＰ−２）で
表される共重合体化合物の代わりに、例示化合物（ＣＰ
−１２）（重量平均分子量；３２５００）を用いた以外
は実施例３１と同様にして電子写真感光体を作製し、実
施例３１と同様の試験を行った。Example 38 In Example 31, oxytitanium phthalocyanine (T-22S, manufactured by Sanyo Dyestuff) was used in place of the τ-type non-metallic phthalocyanine as the charge generating agent, and the compound (C
The compound (CT1-6) is used instead of the charge transfer agent represented by T1-13), and the compound (CP-1) is used instead of the copolymer compound represented by the compound (CP-2).
-12) An electrophotographic photosensitive member was prepared in the same manner as in Example 31 except that (weight average molecular weight: 32500) was used, and the same test as in Example 31 was performed.

【０２１７】実施例３９ 実施例３１において、電荷発生剤としてτ型無金属フタ
ロシアニンの代わりに、オキシチタニウムフタロシアニ
ン（山陽色素製、Ｔ−２２Ｓ）を用い、例示化合物（Ｃ
Ｔ１−１３）で表される電荷移動剤の代わりに、例示化
合物（ＣＴ３−１３）を用い、例示化合物（ＣＰ−２）
で表される共重合体化合物の代わりに、例示化合物（Ｃ
Ｐ−２９）（重量平均分子量；４９０００）を用いた以
外は実施例３１と同様にして電子写真感光体を作製し、
実施例３１と同様の試験を行った。Example 39 In Example 31, oxytitanium phthalocyanine (T-22S, manufactured by Sanyo Dyestuff) was used in place of the τ-type metal-free phthalocyanine as the charge generating agent, and the exemplified compound (C
Exemplified compound (CP-2) using the exemplified compound (CT3-13) instead of the charge transfer agent represented by T1-13)
In place of the copolymer compound represented by
An electrophotographic photoreceptor was prepared in the same manner as in Example 31, except that P-29) (weight average molecular weight; 49000) was used.
The same test as in Example 31 was performed.

【０２１８】実施例４０ 実施例３１において、電荷発生剤としてτ型無金属フタ
ロシアニンの代わりに、オキシチタニウムフタロシアニ
ン（山陽色素製、Ｔ−２２Ｓ）を用い、例示化合物（Ｃ
Ｔ１−１３）で表される電荷移動剤の代わりに、例示化
合物（ＣＴ３−７）を用い、例示化合物（ＣＰ−２）で
表される共重合体化合物の代わりに、例示化合物（ＣＰ
−４５）（重量平均分子量；３４０００）を用いた以外
は実施例３１と同様にして電子写真感光体を作製し、実
施例３１と同様の試験を行った。Example 40 In Example 31, oxytitanium phthalocyanine (T-22S, manufactured by Sanyo Dyestuff) was used in place of the τ-type metal-free phthalocyanine as the charge generating agent, and the compound (C)
The compound (CT3-7) is used instead of the charge transfer agent represented by T1-13), and the compound (CP) is substituted for the copolymer compound represented by the compound (CP-2).
-45) An electrophotographic photosensitive member was prepared in the same manner as in Example 31 except that (weight average molecular weight; 34000) was used, and the same test as in Example 31 was performed.

【０２１９】比較例１６ 実施例３１において、例示化合物（ＣＰ−２）で表され
る共重合体化合物の代わりに、ポリスチレン樹脂（旭化
成製、スタイロン６８５）を用いた以外は実施例３１と
同様にして電子写真感光体を作製し、実施例３１と同様
の試験を行った。Comparative Example 16 The procedure of Example 31 was repeated, except that a polystyrene resin (Styrone 685, manufactured by Asahi Kasei) was used in place of the copolymer compound represented by the exemplified compound (CP-2). Thus, an electrophotographic photosensitive member was manufactured, and the same test as in Example 31 was performed.

【０２２０】比較例１７ 実施例３４において、例示化合物（ＣＰ−６）で表され
る共重合体化合物の代わりに、ポリカーボネート樹脂
（帝人化成製、パンライトＬ−１２５０）を用いた以外
は実施例３４と同様にして電子写真感光体を作製し、実
施例３４と同様の試験を行った。Comparative Example 17 The procedure of Example 34 was repeated, except that a polycarbonate resin (manufactured by Teijin Chemicals Ltd., Panlite L-1250) was used in place of the copolymer compound represented by the exemplified compound (CP-6). An electrophotographic photosensitive member was prepared in the same manner as in Example 34, and the same test as in Example 34 was performed.

【０２２１】比較例１８ 実施例３５において、例示化合物（ＣＰ−１）で表され
る共重合体化合物の代わりに、ポリアリレート樹脂（ユ
ニチカ製、Ｕ−１００Ｄ）を用いた以外は実施例３５と
同様にして電子写真感光体を作製し、実施例３５と同様
の試験を行った。Comparative Example 18 The procedure of Example 35 was repeated except that a polyarylate resin (U-100D, manufactured by Unitika) was used in place of the copolymer compound represented by the exemplary compound (CP-1). In the same manner, an electrophotographic photosensitive member was manufactured, and the same test as in Example 35 was performed.

【０２２２】比較例１９ 実施例３７において、例示化合物（ＣＴ１−９）で表さ
れる電荷移動剤の代わりに、比較化合物（ＥＸ−２）を
用いた以外は実施例３７と同様にして電子写真感光体を
作製し、実施例３７と同様の試験を行った。Comparative Example 19 An electrophotograph was prepared in the same manner as in Example 37 except that the comparative compound (EX-2) was used in place of the charge transfer agent represented by the exemplified compound (CT1-9). A photoreceptor was manufactured and the same test as in Example 37 was performed.

【０２２３】比較例２０ 実施例３８において、例示化合物（ＣＰ−１２）で表さ
れる共重合体化合物の代わりに、ポリエステル樹脂（東
洋紡製、バイロン２２０）を用いた以外は実施例３８と
同様にして電子写真感光体を作製し、実施例３８と同様
の試験を行った。Comparative Example 20 The procedure of Example 38 was repeated except that a polyester resin (manufactured by Toyobo, Byron 220) was used in place of the copolymer compound represented by the exemplified compound (CP-12). Thus, an electrophotographic photosensitive member was manufactured, and the same test as in Example 38 was performed.

【０２２４】比較例２１ 実施例３９において、例示化合物（ＣＰ−２９）で表さ
れる共重合体化合物の代わりに、ポリエステル樹脂（東
洋紡製、バイロン２９０）を用いた以外は実施例３９と
同様にして電子写真感光体を作製し、実施例３９と同様
の試験を行った。Comparative Example 21 The procedure of Example 39 was repeated, except that a polyester resin (manufactured by Toyobo, Byron 290) was used instead of the copolymer compound represented by the exemplified compound (CP-29). Thus, an electrophotographic photosensitive member was manufactured, and the same test as in Example 39 was performed.

【０２２５】比較例２２ 実施例４０において、例示化合物（ＣＴ３−７）で表さ
れる電荷移動剤の代わりに、比較化合物（ＥＸ−３）を
用いた以外は実施例４０と同様にして電子写真感光体を
作製し、実施例４０と同様の試験を行った。Comparative Example 22 An electrophotograph was prepared in the same manner as in Example 40 except that the comparative compound (EX-3) was used in place of the charge transfer agent represented by the exemplified compound (CT3-7). A photoreceptor was manufactured and the same test as in Example 40 was performed.

【０２２６】実施例３１から４０までの電気特性の結果
をを表２３に示し、耐摩耗性試験の結果を表２４に示
す。また、比較例１６から２４までの電気特性の結果を
表２５に示し、耐摩耗性の結果を表２６に示す。Table 23 shows the results of the electrical characteristics of Examples 31 to 40, and Table 24 shows the results of the wear resistance test. Table 25 shows the results of the electrical characteristics of Comparative Examples 16 to 24, and Table 26 shows the results of the abrasion resistance.

【０２２７】[0227]

【表２３】 [Table 23]

【０２２８】[0228]

【表２４】 [Table 24]

【０２２９】[0229]

【表２５】 [Table 25]

【０２３０】[0230]

【表２６】 [Table 26]

【０２３１】上記のように、実施例３１から４０で例示
した感光体は、高感度で繰り返し安定性に優れ、かつ耐
摩耗性に優れているが、実施例３６では感度及び繰り返
し安定性が、他の実施例と比べるとやや劣っている。一
方、比較例１６から２４で例示した感光体は、全体的に
低感度で繰り返し安定性に劣り、耐摩耗性も劣ってい
る。比較例１９、２２は耐摩耗性の面ではそれほど劣っ
ていないが、感度及び繰り返し安定性が劣っている。こ
のように繰り返し安定性が劣っていると、コピー実写評
価では、繰り返しにより実写画像のコントラストが低下
すると共にカブリが発生する。As described above, the photoconductors exemplified in Examples 31 to 40 have high sensitivity, excellent repetition stability, and excellent abrasion resistance. However, in Example 36, the sensitivity and the repetition stability are low. It is slightly inferior to other examples. On the other hand, the photoconductors exemplified in Comparative Examples 16 to 24 are generally low in sensitivity, inferior in repetition stability, and inferior in wear resistance. Comparative Examples 19 and 22 are not so inferior in terms of wear resistance, but are inferior in sensitivity and repetition stability. If the repetition stability is inferior as described above, in the actual copy image evaluation, the repetition lowers the contrast of the actual image and causes fogging.

【０２３２】実施例１から４０で分かるように、導電性
支持体上に少なくとも電荷発生層と電荷移動層からなる
感光層を有する電子写真感光体において、電荷移動層に
バインダー樹脂として、一般式（I）及び（II）で表さ
れる構造単位からなる共重合体化合物を含有させ、かつ
一般式（III）、（IV）、（V）で表される電荷移動剤の
少なくとも１種を含有させることによって、耐摩耗性に
優れ、高感度で繰り返し安定性に優れた電子写真感光体
を提供できる。また、本発明においては、更に無金属フ
タロシアニン、オキシチタニルフタロシアニン、又は一
般式（V）で表されるピラゾール骨格を有するアゾ顔料
を併用することにより、更なる高感度化を図ることがで
き、更に電荷移動剤としては、一般式（III）、（I
V）、（V）で表される化合物を用いることが有効である
が、一般式（III）で表される電荷移動剤は、相対的に
耐摩耗性、感度及び繰り返し安定性が、一般式（IV）、
（V）で表される電荷移動剤よりもやや劣り、一般式（I
V）、（V）で表される電荷移動剤の方がより有効であ
る。As can be seen from Examples 1 to 40, in an electrophotographic photosensitive member having a photosensitive layer comprising at least a charge generating layer and a charge transfer layer on a conductive support, a general formula (B) is used as a binder resin in the charge transfer layer. A copolymer compound comprising the structural units represented by I) and (II) is contained, and at least one of the charge transfer agents represented by the general formulas (III), (IV) and (V) is contained. This makes it possible to provide an electrophotographic photoreceptor having excellent abrasion resistance, high sensitivity and excellent repetition stability. Further, in the present invention, by further using a metal-free phthalocyanine, an oxytitanyl phthalocyanine, or an azo pigment having a pyrazole skeleton represented by the general formula (V), it is possible to further increase sensitivity. As the charge transfer agent, general formulas (III) and (I
Although it is effective to use the compounds represented by V) and (V), the charge transfer agent represented by the general formula (III) has relatively abrasion resistance, sensitivity and repetition stability, (IV),
(V) is slightly inferior to the charge transfer agent represented by the general formula (I
The charge transfer agents represented by (V) and (V) are more effective.

【０２３３】[0233]

【発明の効果】以上から明らかなように、本発明によれ
ば、耐摩耗性に優れ、高感度で、しかも繰り返し安定性
に優れた電子写真感光体を提供することができる。As is apparent from the above, according to the present invention, it is possible to provide an electrophotographic photoreceptor having excellent abrasion resistance, high sensitivity, and excellent repetition stability.

フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｇ０３Ｇ 5/06 ３１５ Ｇ０３Ｇ 5/06 ３１５Ｂ ３２８ ３２８ ３４０ ３４０ ３７２ ３７２ Continued on the front page (51) Int.Cl. 6 Identification symbol FI G03G 5/06 315 G03G 5/06 315B 328 328 340 340 340 372 372

Claims (2)

【特許請求の範囲】[Claims] 【請求項１】 導電性支持体上に少なくとも電荷発生層
と電荷移動層からなる感光層を有する電子写真感光体に
おいて、該電荷移動層がバインダー樹脂として下記一般
式（I）及び（II）で表される構造単位からなる共重合
体化合物を含有し、かつ電荷移動剤として下記一般式
（III）、（IV）、（V）で表される化合物の少なくとも
１種を含有することを特徴とする電子写真感光体。 【化１】 （式（I）中において、Ｒ1、Ｒ2は水素原子、アルキル
基、アリール基、Ｒ1とＲ2で形成する炭素数５〜８の環
状炭化水素残基を表し、Ｒ3、Ｒ4は水素原子、ハロゲン
原子、アルキル基、アリール基を表す。また、ａ、ｂは
１又は２の整数を表す。） 【化２】 （式（II）中において、Ｒ5、Ｒ6は水素原子、ハロゲン
原子、アルキル基、アリール基を表す。また、ｃ、ｄは
１又は２の整数を表す。） 【化３】 （式（III）中において、Ｒ7、Ｒ8、Ｒ9、Ｒ10は水素原
子、アルキル基、アラルキル基、アリール基を示し、Ｒ
9とＲ10は相互に結合して環を形成してもよい。Ｚはイ
ンドリン環の２つの炭素原子と共に飽和の５〜８員環を
形成するのに必要とされる原子群を示す。） 【化４】 （式（IV）中において、Ｒ11及びＲ12はアルキル基、ア
ラルキル基、アリール基又は複素環基を表す。Ｒ13及び
Ｒ14は水素原子、アルキル基、アルコキシ基又はハロゲ
ン原子を表す。） 【化５】 （式（V）中において、Ｒ15、Ｒ16は、水素原子、アル
キル基、アリール基又はスチリル基を表し、少なくとも
１つはアリール基又はスチリル基である。Ｒ17はアルキ
ル基、アラルキル基、又はアリール基を表し、Ｒ18、Ｒ
19は、水素原子、アルキル基、アラルキル基又はアリー
ル基を表し、Ｒ20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す。）1. An electrophotographic photosensitive member having a photosensitive layer comprising at least a charge generating layer and a charge transfer layer on a conductive support, wherein the charge transfer layer is a binder resin represented by the following general formulas (I) and (II): A copolymer compound comprising a structural unit represented by the formula (I), and at least one compound represented by the following general formulas (III), (IV) and (V) as a charge transfer agent. Electrophotographic photoreceptor. Embedded image (In the formula (I), R 1 and R 2 represent a hydrogen atom, an alkyl group, an aryl group, a cyclic hydrocarbon residue having 5 to 8 carbon atoms formed by R 1 and R 2 , and R 3 and R 4 Represents a hydrogen atom, a halogen atom, an alkyl group, or an aryl group, and a and b represent an integer of 1 or 2. (In the formula (II), R 5 and R 6 each represent a hydrogen atom, a halogen atom, an alkyl group, or an aryl group. Further, c and d each represent an integer of 1 or 2.) (In the formula (III), R 7 , R 8 , R 9 , and R 10 represent a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group;
9 and R 10 may combine with each other to form a ring. Z represents an atomic group required to form a saturated 5- to 8-membered ring together with two carbon atoms of the indoline ring. ) (In Formula (IV), R 11 and R 12 represent an alkyl group, an aralkyl group, an aryl group, or a heterocyclic group. R 13 and R 14 represent a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom.) Embedded image (In the formula (V), R 15 and R 16 represent a hydrogen atom, an alkyl group, an aryl group or a styryl group, and at least one is an aryl group or a styryl group. R 17 is an alkyl group, an aralkyl group, Or an aryl group, R 18 , R
19 represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and R 20 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom. ) 【請求項２】 電荷発生層に電荷発生剤として無金属フ
タロシアニン、オキシチタニウムフタロシアニン、アゾ
顔料の少なくとも１種を含有することを特徴とする請求
項１記載の電子写真感光体。2. The electrophotographic photoreceptor according to claim 1, wherein the charge generation layer contains at least one of metal-free phthalocyanine, oxytitanium phthalocyanine, and azo pigment as a charge generation agent.
JP4236097A 1997-02-26 1997-02-26 Electrophotographic photoreceptor Pending JPH10239871A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP4236097A JPH10239871A (en) 1997-02-26 1997-02-26 Electrophotographic photoreceptor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP4236097A JPH10239871A (en) 1997-02-26 1997-02-26 Electrophotographic photoreceptor

Publications (1)

Publication Number Publication Date
JPH10239871A true JPH10239871A (en) 1998-09-11

Family

ID=12633879

Family Applications (1)

Application Number Title Priority Date Filing Date
JP4236097A Pending JPH10239871A (en) 1997-02-26 1997-02-26 Electrophotographic photoreceptor

Country Status (1)

Country Link
JP (1) JPH10239871A (en)

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JP2006072342A (en) * 2004-08-03 2006-03-16 Mitsubishi Chemicals Corp Electrophotographic photoreceptor, cartridge for electrophotography, image forming apparatus and image forming method
US7060404B2 (en) 2001-05-01 2006-06-13 Ricoh Company, Ltd. Electrophotographic photoreceptor, method for manufacturing the electrophotographic photoreceptor and image forming apparatus using the electrophotographic photoreceptor
JP2007108474A (en) * 2005-10-14 2007-04-26 Fuji Electric Device Technology Co Ltd Electrophotographic photoreceptor
JP2007164089A (en) * 2005-12-16 2007-06-28 Kyocera Mita Corp Laminated electrophotographic photoreceptor and image forming apparatus
JP2010111873A (en) * 2006-10-18 2010-05-20 Idemitsu Kosan Co Ltd Polycarbonate copolymer, molded body and optical material including the copolymer
JP2012014157A (en) * 2010-05-31 2012-01-19 Mitsubishi Chemicals Corp Electrophotographic photoreceptor, image forming apparatus, and electrophotographic cartridge
JP2014115620A (en) * 2012-11-19 2014-06-26 Canon Inc Electrophotographic photoreceptor, manufacturing method of electrophotographic photoreceptor, process cartridge, and electrophotographic device

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7060404B2 (en) 2001-05-01 2006-06-13 Ricoh Company, Ltd. Electrophotographic photoreceptor, method for manufacturing the electrophotographic photoreceptor and image forming apparatus using the electrophotographic photoreceptor
US7127196B2 (en) 2001-05-01 2006-10-24 Ricoh Company, Ltd. Electrophotographic photoreceptor, method for manufacturing the electrophotographic photoreceptor and image forming apparatus using the electrophotographic photoreceptor
JP2006072342A (en) * 2004-08-03 2006-03-16 Mitsubishi Chemicals Corp Electrophotographic photoreceptor, cartridge for electrophotography, image forming apparatus and image forming method
JP2007108474A (en) * 2005-10-14 2007-04-26 Fuji Electric Device Technology Co Ltd Electrophotographic photoreceptor
JP2007164089A (en) * 2005-12-16 2007-06-28 Kyocera Mita Corp Laminated electrophotographic photoreceptor and image forming apparatus
JP2010111873A (en) * 2006-10-18 2010-05-20 Idemitsu Kosan Co Ltd Polycarbonate copolymer, molded body and optical material including the copolymer
JP2012014157A (en) * 2010-05-31 2012-01-19 Mitsubishi Chemicals Corp Electrophotographic photoreceptor, image forming apparatus, and electrophotographic cartridge
US8697321B2 (en) 2010-05-31 2014-04-15 Mitsubishi Chemical Corporation Electrophotographic photoreceptor, image-forming apparatus, and electrophotographic cartridge
JP2014115620A (en) * 2012-11-19 2014-06-26 Canon Inc Electrophotographic photoreceptor, manufacturing method of electrophotographic photoreceptor, process cartridge, and electrophotographic device

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