JPH03101738A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

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Publication number
JPH03101738A
JPH03101738A JP23955789A JP23955789A JPH03101738A JP H03101738 A JPH03101738 A JP H03101738A JP 23955789 A JP23955789 A JP 23955789A JP 23955789 A JP23955789 A JP 23955789A JP H03101738 A JPH03101738 A JP H03101738A
Authority
JP
Japan
Prior art keywords
group
weight
charge
layer
photosensitive layer
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
JP23955789A
Other languages
Japanese (ja)
Inventor
Takaaki Ikegami
孝彰 池上
Yasuo Suzuki
康夫 鈴木
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.)
Ricoh Co Ltd
Original Assignee
Ricoh Co 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 Ricoh Co Ltd filed Critical Ricoh Co Ltd
Priority to JP23955789A priority Critical patent/JPH03101738A/en
Publication of JPH03101738A publication Critical patent/JPH03101738A/en
Pending legal-status Critical Current

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  • Photoreceptors In Electrophotography (AREA)

Abstract

PURPOSE:To obtain the electrophotographic sensitive body which is free from an increase in residual potential and has excellent electrostatic charge stability even after repetitive use for a long period of time by incorporating a specific polyhydroxyflavn compd. into a photosensitive layer. CONSTITUTION:The polyhydroxyflavan compd. expressed by formula I is incorporated into the photosensitive layer contg. a charge generating material and charge transfer material on a conductive substrate. In the formula I, R1 to R7 respectively denote a hydrogen atom, hydroxy group, halogen atom, alkyl group, alkenyl group, aryl group, cycloalkl group, alkoxy group, substed. amino group, imino group, heterocyclic group, alkylthio group or acyl group. At least one of R3 to R7 are a hydroxy group. Thus, the electrophotographic sensitive body which has the excellent electrostatic charge stability and is free from the increase in the residual potential even after the repetitive use, i.e. free from the degradation in image density and scumming, and has a long life and high reliability is obtd..

Description

【発明の詳細な説明】 〔産業上の分野〕 本発1jJJは電子写真感光体に係わるものであり、特
に長期間の繰り返し使用時においても、残留電位の上昇
がなく,帯電安定性に優れた電子写真感光体に関する6 〔従来の技術〕 従来から電子写真感光体の光導電素材として知られてい
るものにセレン、硫化カドミウム、酸化亜釦などの無機
物質がある。しかしながら、これら無機物質は電子写真
感光体として要求される光感度,熱安定性,耐久性等の
特性及び製造条件において必ずしも満足できるものでは
ない。例えば、セレンは熱、汚れ等により結晶化しやす
く特性が劣化しやすい。又、製造コスト、耐衝撃性、毒
性等取り扱い上の注意を要するなどの欠点がある。
[Detailed Description of the Invention] [Industrial Field] The present invention 1jJJ relates to electrophotographic photoreceptors, and has excellent charging stability, with no increase in residual potential, especially during repeated use over a long period of time. 6 Regarding Electrophotographic Photoreceptors [Prior Art] Inorganic materials such as selenium, cadmium sulfide, and sulfur oxide have been conventionally known as photoconductive materials for electrophotographic photoreceptors. However, these inorganic materials do not necessarily satisfy the characteristics such as photosensitivity, thermal stability, and durability required for electrophotographic photoreceptors and the manufacturing conditions. For example, selenium tends to crystallize due to heat, dirt, etc., and its properties tend to deteriorate. In addition, it has drawbacks such as manufacturing cost, impact resistance, toxicity, and other issues that require careful handling.

硫化カドミウムを用いた感光体は耐湿性、耐久性に劣り
、又、毒性等の問題がある。酸化亜鉛も、耐湿性,II
Iit久性に劣るという欠点をもつ.これら無機光導電
素材を用いた電子写真感光体に対し、有機光導電性物質
を用いた感光体は軽量性,成膜容易性、製造コストある
いは有機化合物としてのバリエーションの広さから、活
発に研究開発が行なわれるようになっている.例えば、
初期には特公昭50−10496号公報記載のポリビニ
ル力ノレバゾールと2.4.7−トリニトロー9−フル
オレノンを含有した感光体、特公昭48−25658号
公報記載のポリビニル力ルバゾールをピリリウム塩系色
素で増感した感光体、又は、共品錯体を主或分とする感
光体が提案された.しかしながら,これらの感光体は感
度、耐久性の面で−ト分なものではない。
Photoreceptors using cadmium sulfide have poor moisture resistance and durability, and also have problems such as toxicity. Zinc oxide is also moisture resistant, II
It has the disadvantage of poor durability. In contrast to electrophotographic photoreceptors using these inorganic photoconductive materials, photoreceptors using organic photoconductive materials are being actively researched due to their light weight, ease of film formation, manufacturing cost, and wide variation as organic compounds. Development is underway. for example,
Initially, photoreceptors containing polyvinyl rubazole and 2,4,7-trinitro-9-fluorenone as described in Japanese Patent Publication No. 50-10496, and polyvinyl rubazole as described in Japanese Patent Publication No. 48-25658 with a pyrylium salt dye. A sensitized photoreceptor or a photoreceptor based mainly on a conjugate complex has been proposed. However, these photoreceptors are not up to par in terms of sensitivity and durability.

そこで近年では、電荷発生層と電荷輸送層を分離した機
能分離型の感光体が提案され、特公昭55−42380
号記載のクロルダイアンプルーとヒドラゾン化合物を組
み合わせた感光体、電荷発生物質としてはビスアゾ化合
物として特開昭53−133445号公報記載、特開昭
54−21728号公報記載、特開昭54−22834
号公報記載、電荷輸送物質としては特開昭58−198
043号公報、特開昭58− 199352号公報等記
載のものが知られている,しかしながら、これら機能分
離型感光体においても特に耐久性においては満足できる
ものではなく、近年、増々耐久性に対する要求が高まっ
てくる中で、帯電安定性を確保することが無視できない
問題となっている.すなわち,帯電性が低下した場合、
複写機ではコピーの画像濃度低ドをひきおこし、反転現
像方式を用いているレーザープリンターの場合は地肌汚
れを発生する等のplj像品質の低下をひきおこす.こ
れらの問題を解決するために、導電性基板と感光層との
間に中間層を設ける事が提案されている。しかしながら
中間層は、帯電性を安定させるために、バリアー性の高
い高抵抗材料を用いた場合、帯電性は向上するものの、
光感度が低下し、残留電位が上昇するという欠点がある
。また残留電位が上昇しないような比較的抵抗の低い材
料を用いた場合は,帯電安定性が不十分となる。
Therefore, in recent years, a functionally separated type photoreceptor in which a charge generation layer and a charge transport layer are separated has been proposed, and
A photoreceptor comprising a combination of chlordiane blue and a hydrazone compound as described in JP-A-53-133445, JP-A-54-21728, and JP-A-54-22834 as a charge-generating substance.
As described in the publication, the charge transport material is JP-A-58-198.
043, Japanese Patent Application Laid-Open No. 199352, etc. are known. However, even these function-separated type photoreceptors are not particularly satisfactory in terms of durability, and in recent years, there has been an increasing demand for durability. With the increase in charging stability, ensuring charging stability has become an issue that cannot be ignored. In other words, when the chargeability decreases,
In copying machines, this causes low image density when copying, and in laser printers that use a reversal development method, it causes deterioration in PLJ image quality, such as background stains. In order to solve these problems, it has been proposed to provide an intermediate layer between the conductive substrate and the photosensitive layer. However, if a high-resistance material with high barrier properties is used for the intermediate layer in order to stabilize the charging property, although the charging property will improve,
It has the drawbacks of decreased photosensitivity and increased residual potential. Furthermore, if a material with relatively low resistance that does not increase the residual potential is used, charging stability will be insufficient.

一方、感光体を実際に複写機中で使用した場合、コロナ
帯電器より発生するオゾンに感光体がさらされることに
なる.そしてこのオゾンが感光層中の電荷輸送物質等を
酸化し感度低下、残留電位の上昇、又は帯電電位低下を
ひきおこすとの観点から特開昭57−122444号公
報、特開昭61−156052号公報にみられるような
感光層中への酸化防止剤の添加、又、特開昭63−13
5955号公報にみられるような電荷輸送層上にガスバ
リャー性樹脂層を設ける算の堤案がなされている。しか
しながら以上のような対策によっても残留電位の上昇が
生じる、感度低下等の併害をもつ、耐久性の向上がなお
不充分である等の欠点があり、未だ満足できる感光体は
得られていない。
On the other hand, when a photoreceptor is actually used in a copying machine, it is exposed to ozone generated by a corona charger. From the viewpoint that this ozone oxidizes the charge transporting substance etc. in the photosensitive layer, causing a decrease in sensitivity, an increase in residual potential, or a decrease in charging potential, Japanese Patent Application Laid-Open No. 122444/1982 and No. 156052/1989 are published. The addition of an antioxidant to the photosensitive layer as seen in JP-A-63-13
A proposal has been made in which a gas barrier resin layer is provided on the charge transport layer as seen in Japanese Patent No. 5955. However, even with the above measures, there are drawbacks such as an increase in residual potential, a decrease in sensitivity, and insufficient improvement in durability, and a satisfactory photoreceptor has not yet been obtained. .

〔発明が解決しようとする課題〕[Problem to be solved by the invention]

本発明は上記従来の問題点を解決するものであって,具
体的には耐オゾン性に優れ、繰り返し使用しても帯電安
定性に優れ、残留電位が上昇しないすなわち画像濃度低
下や地汚れを生じない良好な画像を与える電子写真感光
体を提供することをその課題とする。
The present invention solves the above-mentioned conventional problems. Specifically, the present invention has excellent ozone resistance, excellent charging stability even after repeated use, and no increase in residual potential, which means that it does not reduce image density or cause background stains. The object of the present invention is to provide an electrophotographic photoreceptor that can give good images without causing image formation.

〔課題を解決するための手段〕[Means to solve the problem]

本発明によれば、導電性支持体上に電荷発生物質と電荷
輸送物質とを含有する感光層を有する電子写真感光体に
おいて、前記感光層中に下記一般式(Nに示すポリヒド
ロキシフラバン化合物を含有することを特徴とする電子
写真感光体.(式中、1{1〜R,はそれぞれ,水素原
子、ヒドロキシ基,ハロゲン原子,アルキル基、アルケ
ニル基、アリール基、シクロアルキル基、アルコキシ基
、置換アミノ基,イミノ基、複素環基、アルキルキオ基
又はアシル基を表わす。但し、R1〜R7のうち少なく
とも一つは,ヒドロキシ基である。) が提供される. 本発明の電子写真感光体は感光層中にポリヒドロキシフ
ラバン化合物を含有させたことから繰り返し使用によっ
ても帯電安定性に優れ、かつ残留電位の上昇しない、し
たがって画像濃度低下や地汚れのない高寿命,高信頼性
のものとなる。
According to the present invention, in an electrophotographic photoreceptor having a photosensitive layer containing a charge generating substance and a charge transporting substance on a conductive support, a polyhydroxyflavan compound represented by the following general formula (N) is incorporated in the photosensitive layer. An electrophotographic photoreceptor characterized by containing (in the formula, 1 {1 to R, respectively, a hydrogen atom, a hydroxy group, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a cycloalkyl group, an alkoxy group, represents a substituted amino group, imino group, heterocyclic group, alkylkio group, or acyl group (provided that at least one of R1 to R7 is a hydroxy group).The electrophotographic photoreceptor of the present invention Since the photosensitive layer contains a polyhydroxyflavan compound, it has excellent charging stability even after repeated use, and the residual potential does not increase. Therefore, it has a long life and high reliability with no decrease in image density or background smearing. .

本発明に用いることができるポリヒドロキシフラバン化
合物の具体例としては、たとえif以下のような化合物
を例示することができる。
Specific examples of polyhydroxyflavan compounds that can be used in the present invention include compounds as shown below.

本発明電子写真感光体は.前記一般式〔!〕で示される
ポリヒドロシフラパン化合物を感光屑中に含有させるこ
とにより耐久性の優れたものとなるが、その理由につい
ては現時点では明らかではないが,感光J&構或物質一
特に結着剤樹脂一との相溶性が優れること,他の感光層
構成物質と反応する等の悪影響がないこと,電荷担体の
トラップとして働かないこと、ラジカル物質と速やかに
反応し、トラップの生成を防止する能力が優れること等
が挙げられる. 本発明においては、・前記ポリオキシフラバン化合物に
対しては、さらに保存性、耐熱性向上の観点から2次劣
化防止剤を添加することが好ましい。
The electrophotographic photoreceptor of the present invention is. The above general formula [! ] By incorporating the polyhydrosyfurapane compound shown in the photosensitive scrap into the photosensitive scrap, it becomes highly durable.The reason for this is not clear at present, but the photosensitive material, especially the binder resin, It has excellent compatibility with other photosensitive layer constituents, it does not react with other materials constituting the photosensitive layer, it does not act as a trap for charge carriers, and it has the ability to quickly react with radical substances and prevent the formation of traps. Examples include being excellent. In the present invention, it is preferable to further add a secondary deterioration inhibitor to the polyoxyflavan compound from the viewpoint of improving storage stability and heat resistance.

2次劣化防止剤としては燐系化合物,硫黄系化合物がよ
く知られているが、特に燐系化合物をもちいることが好
ましい。燐系化合物の具体例としては、′たとえばトリ
ス(ノニルフェニル)ホスファイト、トリス(p−te
rt−オクチルフェニル)ホスファイト,Lリス(2,
4.6−トリス(α−フェニルエチル)〕ホスファイト
、トリス(p−2−ブテニルフェニル)ホスファイト,
ビス(p−ノニルフエニル)シクロヘキシルホスファイ
ト、トリス(2.4−ジーtart−ジブチルフェニル
)ホスファイト、ジ(2,4−ジーtert−ジブチル
フェニル)ペンタエリスリトールジホスファイト、ジス
テアリルペンタエリスリトールジホスファイト、4,4
′−イソプロピリデンージフェノールアルキルホスファ
イト、テ1・ラトリデシル−4.4’−プチリデンービ
ス(3−メチル−6−tert−プチルフェノール)ジ
ホスファイト、テトラキス(2,4−ジーtert−プ
チルフェニル)−4.4’−ビフエニレンジホスファイ
ト、2,6−ジーtert−ブチルー4−メチルフェニ
ル・フェニル・ペンタエリスリトールジホスファイト、
2,6−ジーtert−ブチルー4−メチルフェニル・
メチル・ペンタエリスリトール・ジホスファイト、2,
6−ジーtert−ブチルー4−エチルフェニル・ステ
アリル・ペンタエリスリトールジホスファイト、ジ(2
,6−ジーtert−ブチルー4−メチルフェニル)ペ
ンタエリスリトールジホスファイト、2,6−ジーte
rt−アミルー4−メチルフェニル・フェニル・ペンタ
エリスリトールジホスファイト等が挙げられるが、これ
らの化合物は2種以上併用してもよい。
Although phosphorus compounds and sulfur compounds are well known as secondary deterioration inhibitors, it is particularly preferable to use phosphorus compounds. Specific examples of phosphorus compounds include tris(nonylphenyl)phosphite, tris(p-te
rt-octylphenyl) phosphite, L-lis(2,
4.6-tris(α-phenylethyl)]phosphite, tris(p-2-butenylphenyl)phosphite,
Bis(p-nonylphenyl)cyclohexyl phosphite, tris(2,4-di-tert-dibutylphenyl) phosphite, di(2,4-di-tert-dibutylphenyl) pentaerythritol diphosphite, distearyl pentaerythritol diphosphite ,4,4
'-Isopropylidene-diphenol alkyl phosphite, Te1-latridecyl-4,4'-butylidene-bis(3-methyl-6-tert-butylphenol) diphosphite, Tetrakis(2,4-di-tert-butylphenyl)-4 .4'-biphenylene diphosphite, 2,6-di-tert-butyl-4-methylphenyl phenyl pentaerythritol diphosphite,
2,6-di-tert-butyl-4-methylphenyl
Methyl pentaerythritol diphosphite, 2,
6-di-tert-butyl-4-ethylphenyl stearyl pentaerythritol diphosphite, di(2
,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, 2,6-di-tert-butyl-4-methylphenyl)
Examples include rt-amyl-4-methylphenyl, phenyl, pentaerythritol diphosphite, and two or more of these compounds may be used in combination.

本発明の電子写真感光体に用いることができる電荷発生
物質としては光を吸収して電荷担体を発生するものであ
れば無機物質,有機物質いずれも用いることができる。
As the charge generating substance that can be used in the electrophotographic photoreceptor of the present invention, both inorganic and organic substances can be used as long as they absorb light and generate charge carriers.

焦機物質としては例えば、無定形セレン、三方晶系セレ
ン、セレンーヒ素合金、セレンーテルル合金,硫化カド
ミウム、酸化亜鉛、無定形シリコン等が挙げられる。
Examples of the pyrophoric material include amorphous selenium, trigonal selenium, selenium-arsenic alloy, selenium-tellurium alloy, cadmium sulfide, zinc oxide, and amorphous silicon.

有機物質としては例えば、金属フタ口シアニン及び、無
金属フタ口シアニン等のフタロシアニン系顔料、アズレ
ニウム塩顔料、スクエアリンク酸メチン顔料、カルバゾ
ール骨格を有するアゾ顔料,トリフェンルアミン骨格を
有するアゾ顔料、ジフェニルアミン骨格を有するアゾ顔
料、ジベンゾチオフェン骨格を有するアゾ顔料、オキサ
ジアゾール骨格を有するアゾ顔料、フルオレノン骨格を
有するアゾ顔料、ビススチルベン骨格を有するアゾ顔料
、ジスチリルオキサジアゾール骨格を有するアゾ顔料、
ジスチリル力ルバゾール骨格を有するアゾ顔料,ペリレ
ン系顔料、アントラキノン系又は多環キノン系顔料,キ
ノンイミン系顔料、ジフエニルメタン及びトリフェニル
メタン系顔料、ペンゾキノン及びナフトキノン系顔料,
シアニン及びアゾメチン系顔料、インジゴイド系顔料、
ビスベンズイミダゾール系材料等が挙げられる。
Examples of organic substances include phthalocyanine pigments such as metal-capturing cyanine and non-metallic capping-cyanine, azulenium salt pigments, methine squarate pigments, azo pigments having a carbazole skeleton, azo pigments having a triphenylamine skeleton, and diphenylamine. Azo pigments having a skeleton, azo pigments having a dibenzothiophene skeleton, azo pigments having an oxadiazole skeleton, azo pigments having a fluorenone skeleton, azo pigments having a bisstilbene skeleton, azo pigments having a distyryl oxadiazole skeleton,
Azo pigments having a distyrylic rubazole skeleton, perylene pigments, anthraquinone or polycyclic quinone pigments, quinone imine pigments, diphenylmethane and triphenylmethane pigments, penzoquinone and naphthoquinone pigments,
Cyanine and azomethine pigments, indigoid pigments,
Examples include bisbenzimidazole materials.

本発明の電子写真感光体に用いることができる電荷輸送
物質としては例えば,ポリーN−ビニル力ルバゾールお
よびその誘導体、ポリーγ一カルバゾリルエチルグルタ
メートおよびその誘導体、ピレンーホルムアルデヒド縮
合物およびその誘導体、ポリビニルピレン、ポリビニル
フエナントレン,オキサゾール誘導体,オキサジアゾー
ル誘導体,イミゾール誘導体、トリフエニルアミン誘導
体.9−(p−ジエチルアミノスチリル)アントラセン
、1,l−ビス−(4−ジベンジルアミノフェニル)プ
ロパン、スチリルアントラセン、スチリルピラゾリンζ
フエニルヒドラゾン類,α−フェニルスチルベン誘導体
、チアゾール誘導体、トリアゾール誘導体、フェナジン
誘導体、アクリジン誘導体、ペンゾフラン誘導体、ペン
ズイミダゾール誘導体、チオフェン誘導体等が挙げられ
る。
Examples of charge transport materials that can be used in the electrophotographic photoreceptor of the present invention include poly-N-vinyl Rubazole and its derivatives, poly-γ-carbazolylethyl glutamate and its derivatives, pyrene-formaldehyde condensate and its derivatives, Polyvinylpyrene, polyvinylphenanthrene, oxazole derivatives, oxadiazole derivatives, imizole derivatives, triphenylamine derivatives. 9-(p-diethylaminostyryl)anthracene, 1,l-bis-(4-dibenzylaminophenyl)propane, styryl anthracene, styryl pyrazoline ζ
Examples include phenylhydrazones, α-phenylstilbene derivatives, thiazole derivatives, triazole derivatives, phenazine derivatives, acridine derivatives, penzofuran derivatives, penzimidazole derivatives, and thiophene derivatives.

特にこのうちド記一般式(■)で示される芳香族アミン
化合物が好ましい。
Among these, aromatic amine compounds represented by the general formula (■) are particularly preferred.

?式中,R■と83は置換又は末置換のフェニル基、ナ
フチル基およびポリフェニル基から選ばれる芳香族環基
を示し、R3は置換又は末置換のアリール基,アルキル
基、アルコキシ基又は複素環式芳香族基を示す。) 本発明の電子写真感光体の感光層は、電待発生層、電荷
輸送層を組み合わせて,単層型もしくは、機能分離型を
とることができる。
? In the formula, R■ and 83 represent a substituted or terminally substituted aromatic ring group selected from a phenyl group, a naphthyl group, and a polyphenyl group, and R3 represents a substituted or terminally substituted aryl group, alkyl group, alkoxy group, or heterocyclic group. The formula represents an aromatic group. ) The photosensitive layer of the electrophotographic photoreceptor of the present invention can be of a single layer type or a functionally separated type by combining an electric current generation layer and a charge transport layer.

層構成としては単層型の場合、導電性基体の上に、結着
剤中に電荷発生物質、電荷輸送物質を分散させた感光層
を設ける。
In the case of a single layer structure, a photosensitive layer in which a charge generating substance and a charge transporting substance are dispersed in a binder is provided on a conductive substrate.

機能分離型の場合は、基体上に電荷発生物質及び結着剤
を含む電荷発生層,その上に電荷輸送物質及び結着剤を
含む電荷輸送層を形或するものであるが,正帯電型とす
る場合には、電荷発生層、電荷輸送層を逆に積層しても
よい.なお、機能分離型の場合、電荷発生層中に電荷輸
送物質を含有させてもよい、特に正帯電構成の場合感度
が良好となる。
In the case of a functionally separated type, a charge generation layer containing a charge generation substance and a binder is formed on the substrate, and a charge transport layer containing a charge transport substance and a binder is formed on top of the charge generation layer, but a positively charged type In this case, the charge generation layer and the charge transport layer may be stacked in reverse order. In the case of a functionally separated type, a charge transport substance may be contained in the charge generation layer. In particular, in the case of a positively charged structure, the sensitivity is improved.

又、接着性、電荷プロソキング性を向」ニさせるために
感光層と基体との間に中間層を設けてもよい。さらに耐
摩耗性等、機械的耐久性を向上させるために感光層上に
保護屑を設けてもよい。電荷発生層、電荷輸送層及び分
散型感光層形成時に用いる結着剤としては、ポリカーボ
ネート(ビスフェノールAタイプ、ビスフェノールZタ
イプ),ポリエステル、メタクリル樹脂、アクリル樹脂
,ポリエチレン、塩化ビニル、酢酸ビニル、ポリスチレ
ン、フェノール樹脂、エポキシ樹脂、ポリウレタン、ポ
リ塩化ビニリデン,アルキッド樹脂、シリコン樹脂、ポ
リビニル力ルバゾール、ポリビニルブチラール、ポリビ
ニルホルマール、ポリアリレート、ポリアクリルアミド
、ボリアミド、フエノキシ樹脂などが用いられる.これ
らのパインダ一はtit独又は2種以上の混合物として
用いることができる。
Further, an intermediate layer may be provided between the photosensitive layer and the substrate in order to improve adhesion and charge processing properties. Furthermore, protective dust may be provided on the photosensitive layer in order to improve mechanical durability such as abrasion resistance. Binders used in forming the charge generation layer, charge transport layer and dispersed photosensitive layer include polycarbonate (bisphenol A type, bisphenol Z type), polyester, methacrylic resin, acrylic resin, polyethylene, vinyl chloride, vinyl acetate, polystyrene, Phenol resin, epoxy resin, polyurethane, polyvinylidene chloride, alkyd resin, silicone resin, polyvinyl rubber, polyvinyl butyral, polyvinyl formal, polyarylate, polyacrylamide, polyamide, phenoxy resin, etc. are used. These binders can be used alone or as a mixture of two or more kinds.

以上のような層構成,物質を用いて感光体k作或する場
合には、膜厚、物質の割合に好ましい範囲がある。
When producing a photoreceptor using the layer structure and material described above, there is a preferable range for the film thickness and the proportion of the material.

負征電型(基体/電ク■発生層/電荀輸送層の積層)の
場合、電荷発生89において、電荷発生物質に対する結
着剤の割合は0〜400重量2、膜Iヴは0.1〜5μ
和が好ましい。電荷輸送Jケにおいては結着剤に対する
電荷輸送物質の割合は、20〜200重量2.膜J1メ
は5〜50μ陽とするのが好ましい。
In the case of a negative charge type (laminated substrate/electric charge generating layer/electron transport layer), in the charge generation 89, the ratio of the binder to the charge generating substance is 0 to 400 by weight2, and the membrane Iv is 0. 1~5μ
Japanese is preferred. In charge transport J-ke, the ratio of charge transport substance to binder is 20 to 200% by weight. The thickness of the film J1 is preferably 5 to 50 μm.

正帯電型(基体/電荷輸送M/電荷発生層の積層)の場
合、電荷輸送層においては、結着剤に対する電荀輸送物
質の割合は,20〜200重量算、膜厚は5〜50μm
とするのが好ましい9電荷発生層においては電荷発生物
質を結着剤に対し10〜500重1じ含有することが好
ましい。さらに電荷発生層中には電荷輸送物質を含イf
させることが好ましく、含有させることにより残留電位
の抑制,感度の向上に対し効果をもつ。この場合の電荷
輸送物質は結着剤に対し20〜200重ffi%含有さ
せることが好ましい。
In the case of a positively charged type (laminated substrate/charge transport M/charge generation layer), in the charge transport layer, the ratio of the charge transport substance to the binder is 20 to 200% by weight, and the film thickness is 5 to 50 μm.
The charge generating layer preferably contains 10 to 500 parts by weight of the charge generating substance based on the binder. Furthermore, the charge generation layer contains a charge transport substance.
It is preferable to include it, and its inclusion has the effect of suppressing residual potential and improving sensitivity. In this case, it is preferable that the charge transport material is contained in an amount of 20 to 200% by weight of the binder.

なお膜/’Xは0.1〜10pmが好ましい。単層型の
場合は結着剤に対する電荷輸送物質及び電荷発生物質の
割合はそれぞれ50〜150ffi4a%、10〜50
重i%とするのが好まし<1漠厚は5〜50μmとする
のが好ましい。
Note that the film/'X is preferably 0.1 to 10 pm. In the case of a single layer type, the ratio of the charge transport substance and the charge generation substance to the binder is 50 to 150ffi4a% and 10 to 50%, respectively.
It is preferable that the weight is i%<1, and the thickness is preferably 5 to 50 μm.

又,本発明のポリヒドロキシフラバン化合物の感光層へ
の添加量としては、機能分離型の場合、電前輸送層に添
加する場合は電倚輸送物質に対し0.Ol〜10.0重
ffl%であることが好ましい.電荷発生層中に添加す
る場合は電荀発生物質に対し0.1〜20.0重址zで
あることが好ましい。分散型の場合は、<t r:i輸
送物質に対し0.01−5.0重量2添加することが好
ましい。
In addition, the amount of the polyhydroxyflavan compound of the present invention to be added to the photosensitive layer is 0.00% relative to the charge transport material when it is added to the charge transport layer in the case of a functionally separated type. It is preferable that it is 10.0% by weight. When added to the charge generation layer, it is preferably added in an amount of 0.1 to 20.0% by weight based on the charge generation material. In the case of a dispersed type, it is preferable to add 0.01 to 5.0 weight 2 to <t r:i transport substance.

前記一般式CI)で示されるポリヒドロキシフラバン化
合物の添加量が前記下限値より少ない場合は添加による
高耐久化の効果は得られず、前記上限値より多い場合は
,感度低下等悪影響をひきおこす。
If the amount of the polyhydroxyflavan compound represented by the general formula CI) is less than the lower limit, the effect of increasing durability cannot be obtained, and if it is more than the upper limit, it will cause adverse effects such as decreased sensitivity.

本発明で用いる前記ポリヒドロキシフラバン化合物は機
能分離型感光体の場合、電荷発生JH.電荷輸送層、い
ずれの層に添加してもよい。これは感光層塗布時におい
て塗布液分散媒、又は溶媒により本発明で用いるポリヒ
ドロキフラバン化合物の他の層への拡散が盛んに行なわ
れているためと考える。
In the case of a functionally separated type photoreceptor, the polyhydroxyflavan compound used in the present invention is used in charge generation JH. It may be added to any charge transport layer. This is considered to be because the polyhydroxyflavan compound used in the present invention is actively diffused into other layers by the coating liquid dispersion medium or solvent during coating of the photosensitive layer.

必要に応じて設けられる申間層としては、一般には樹脂
を主成分とするが、これらの樹脂はその上に感光Rlを
溶剤で塗布することを考えると、一般の有機溶剤に対し
て耐溶剤性の高い樹脂であることが望ましい。このよう
な樹脂としては、ポリビニルアルコール、カゼイン、ポ
リアクリル酸ナトリウム等の水溶性樹脂、共重合ナイロ
ン、メトキシメチル化ナイロン等のアルコール可溶性樹
脂,ポリウレタン、メラミン樹脂、フェノール樹脂、ア
ルキッドーメラミン樹脂、エボキシ樹脂等,三次元網目
構造を形成する硬化型樹脂などが挙げられる。
The interlayer provided as necessary is generally made of resin as its main component, but considering that the photosensitive Rl is applied thereon with a solvent, these resins are solvent resistant to general organic solvents. It is desirable that the resin has high properties. Examples of such resins include water-soluble resins such as polyvinyl alcohol, casein, and sodium polyacrylate; alcohol-soluble resins such as copolymerized nylon and methoxymethylated nylon; polyurethane; melamine resins; phenolic resins; alkyd-melamine resins; Examples include curable resins that form a three-dimensional network structure, such as epoxy resins.

また中間層にはモアレ防止、残留電位の低減等のために
酸化チタン、シリカ、アルミナ、酸化ジルコニウム、酸
化スズ、酸化インジウム等で例示できる金属酸化物の微
粉末顔料を加えてもよい.また電荷発生層、電荷輸送層
を形或するに際し使用される溶剤あるいは分散媒として
は. N,N’一ジメチルホルムアミド、アセ1ヘン、
メチルエチルケトン,シクロヘキサノン、ベンゼン、ト
ルエン、キシレン、クロロホルム、1,2−ジクロ口エ
タン、ジクロ口メタン、モノクロルベンゼン、テトラヒ
ト口フラン、ジオキサン、メタノール、エタノール,イ
ソプロパノール、酢酸エチル、酢酸ブチル、ジメチルス
ルホキシド等をt;Sけることができる。
Further, fine powder pigments of metal oxides such as titanium oxide, silica, alumina, zirconium oxide, tin oxide, and indium oxide may be added to the intermediate layer to prevent moire and reduce residual potential. Also, as a solvent or dispersion medium used in forming the charge generation layer and charge transport layer. N,N'-dimethylformamide, ace-1hen,
Methyl ethyl ketone, cyclohexanone, benzene, toluene, xylene, chloroform, 1,2-dichloroethane, dichloromethane, monochlorobenzene, tetrahydrofuran, dioxane, methanol, ethanol, isopropanol, ethyl acetate, butyl acetate, dimethyl sulfoxide, etc. ;S can be thrown.

感光層を形或する方法としては電荷発生層、電荷輸送層
の塗工液に基体を浸漬する方法、塗工液を基体にスプレ
ーする方法などが用いられる。
The photosensitive layer may be formed by immersing the substrate in a coating solution for the charge generation layer or charge transport layer, or by spraying the coating solution onto the substrate.

本発明の電子写真感光体に用いられる基体としては,ア
ルミニウム、黄銅,ステンレス,ニッケルなどの金属ド
ラム及びシー1へ、ポリエチレンテレフタレート、ポリ
プロピレン、ナイロン、紙などの材料にアルミニウム、
ニッケルなどの金属を蒸着するか,あるいは酸化チタン
、酸化スズ、カ−ボンブラックなどの導電性物質を適当
なバインダーとともに塗布して導電処理したプラスチッ
ク、紙等のシート状または円筒状基体があげられる.〔
発明の効果〕 本発明の電子写真感光体は、前記構成からなるので長期
の繰り返し使用によっても帯電性等の感光体特性が劣化
しないため,その実用的価値が極めて高いものである. 〔実施例〕 以下、実施例により本発明を更に詳細に説明する。
Substrates used in the electrophotographic photoreceptor of the present invention include metal drums and sheets made of aluminum, brass, stainless steel, nickel, etc., materials such as polyethylene terephthalate, polypropylene, nylon, paper, aluminum,
Examples include sheet-like or cylindrical substrates made of plastic, paper, etc., which have been treated to be conductive by vapor-depositing metals such as nickel, or by coating conductive substances such as titanium oxide, tin oxide, carbon black, etc. together with a suitable binder. .. [
[Effects of the Invention] Since the electrophotographic photoreceptor of the present invention has the above-mentioned structure, the photoreceptor characteristics such as chargeability do not deteriorate even after repeated use over a long period of time, and therefore its practical value is extremely high. [Example] Hereinafter, the present invention will be explained in more detail with reference to Examples.

実施例l アルキッド樹脂〔ベッコゾール1307−60−EL(
大日本井ンキ化学工業社!))15重量部、メラミン樹
脂〔スーパーベッカミンG−821−60(大日本イン
キ化学工業社製))10重量部をメチルエチルケトン1
50重量部に溶解し、これに酸化チタン粉末〔タイペー
クCR−EL(石原産業社製)〕90重量部を加え,ボ
ールミルでl2時間分散し,中間層用塗布液を作威した
Example l Alkyd resin [Beccosol 1307-60-EL (
Dainippon Ink Chemical Industry Co., Ltd.! )) 15 parts by weight, 10 parts by weight of melamine resin [Super Beckamine G-821-60 (manufactured by Dainippon Ink & Chemicals)], 1 part by weight of methyl ethyl ketone
To this was added 90 parts by weight of titanium oxide powder [Tiepeke CR-EL (manufactured by Ishihara Sangyo Co., Ltd.)] and dispersed in a ball mill for 12 hours to prepare a coating solution for an intermediate layer.

これを厚さ0.20のアルミニウム板(A1080(住
友軽金属社製))に塗布、140℃、20分間乾燥し厚
さ2μmの中間層を形成した。
This was applied to an aluminum plate (A1080 (manufactured by Sumitomo Light Metals)) with a thickness of 0.20, and dried at 140° C. for 20 minutes to form an intermediate layer with a thickness of 2 μm.

次にポリビニルブチラール樹脂〔エスレックBL−S(
積水化学工業社製)〕4重量部をシクロヘキサンン15
0重量部に溶解し、これに下記構造式(a)に示す 次に、ポリカーボネート樹脂〔パンライトK−1300
(帝人化或社i!!2)310重量部、シリコンオイル
(KF−50(信越化学工業社′!M))0.002重
量部をテトラヒト口フラン83重量部に溶解し、これに
下記構造式(b)に示す電荷輸送物質7重量部と トリアスアゾ顔料10重量部を加え,ボールミルで48
時間分散し、さらにシクロヘキサノン210重量部を加
えて3時間分散を行った。これを容器に取り出し固形分
が1.5重f%となるようにシクロヘキサノンを希釈し
た。こうして得られた電荷発生層用塗布液を前記中間層
上に塗布、130℃20分間乾燥し厚さ0.2μmの電
荷発生層を形成した。
Next, polyvinyl butyral resin [S-LEC BL-S (
(manufactured by Sekisui Chemical Co., Ltd.)] 4 parts by weight of cyclohexane 15
0 parts by weight, and then polycarbonate resin shown in the following structural formula (a) [Panlite K-1300
(Teijin Kaorisha i!!2) and 0.002 parts by weight of silicone oil (KF-50 (Shin-Etsu Chemical Co., Ltd.'!M)) were dissolved in 83 parts by weight of tetrahydrofuran, and the following structure was added to this. Add 7 parts by weight of the charge transport substance shown in formula (b) and 10 parts by weight of the triazo pigment, and mix 48 parts by weight with a ball mill.
After time dispersion, 210 parts by weight of cyclohexanone was further added and dispersion was carried out for 3 hours. This was taken out into a container and cyclohexanone was diluted so that the solid content was 1.5% by weight. The charge generation layer coating liquid thus obtained was applied onto the intermediate layer and dried at 130° C. for 20 minutes to form a charge generation layer having a thickness of 0.2 μm.

例示化合物Ncilのポリヒドロキシフラバン化合物を
0.07重量部加え溶解して電荷輸送塗布液を作或した
。これを前記電荷発生層上に塗布、130℃20分間乾
燥し厚さ20μmの電荷輸送層を形戊した。
A charge transport coating liquid was prepared by adding and dissolving 0.07 parts by weight of a polyhydroxyflavan compound of the exemplified compound Ncil. This was applied onto the charge generation layer and dried at 130° C. for 20 minutes to form a charge transport layer with a thickness of 20 μm.

以上のようにして実施例1の電子写真感光体を作成した
The electrophotographic photoreceptor of Example 1 was produced in the manner described above.

実施例2,3 実施例1において、例示化合物Nα1のかわりにそれぞ
れ例示化合物N(128,66のポリヒドロキシフラバ
ン化合物を用いたほかは実施例1と同様にして実施例2
,3の電子写真感光体を作威した。
Examples 2 and 3 Example 2 was carried out in the same manner as in Example 1 except that exemplified compound N (128 and 66 polyhydroxyflavan compounds were used in place of exemplified compound Nα1).
, 3 electrophotographic photoreceptors were created.

比較例1 実施例1において、例示化合物Nnlのポリヒドロキシ
フラバン化合物を添加しないほかは実施例1と同様にし
て比較例1の電子写真感光体を作或した。
Comparative Example 1 An electrophotographic photoreceptor of Comparative Example 1 was prepared in the same manner as in Example 1 except that the polyhydroxyflavan compound of the exemplified compound Nnl was not added.

比較例2〜4 実施例1において、例示化合物Nα1のポリヒドロキシ
フラバン化合物の代わりに下記に示す比較化合物1.2
および3を各0.07重量部添加したほかは実施例1と
同様にして比較例2,3.4の電子写真感光体を作成し
た, 比較化合物1(スミライザ−MOP−S :住友化学社
製)比較化合物2(スミライザーTPM:住友化学社製
)CH20H,COOC..H,, ぽ S t CHよCH2C00C14H29 比較化合物3(MARK PEP−24 :アデカアー
ガス社製)実施例4 アルコール可溶性ポリアミド(CM−8000(東レ社
製)〕3重量部をMeOH/n−BuOH:8/ 2の
混合溶媒100重量部に加熱溶解し中間層用塗工液を作
成した,これを厚さ0.21Ilmのアルミニウム板(
AI(180(住友軽金属社製)〕に京布、120℃1
0分間乾燥して厚さ0.2μmの中間層を形成した。
Comparative Examples 2 to 4 In Example 1, Comparative Compound 1.2 shown below was used instead of the polyhydroxyflavan compound of Exemplary Compound Nα1.
Electrophotographic photoreceptors of Comparative Examples 2 and 3.4 were prepared in the same manner as in Example 1 except that 0.07 parts by weight of each of Comparative Compound 1 (Sumilyzer-MOP-S: manufactured by Sumitomo Chemical Co., Ltd.) was added. ) Comparative Compound 2 (Sumilyzer TPM: manufactured by Sumitomo Chemical Co., Ltd.) CH20H, COOC. .. H,, PoS t CH yo CH2C00C14H29 Comparative compound 3 (MARK PEP-24: manufactured by Adeka Argus) Example 4 3 parts by weight of alcohol-soluble polyamide (CM-8000 (manufactured by Toray Industries)) was mixed with MeOH/n-BuOH: 8 / 2 was heated and dissolved in 100 parts by weight of a mixed solvent to create an intermediate layer coating solution, which was coated on an aluminum plate with a thickness of 0.21 lm (
AI (180 (manufactured by Sumitomo Light Metal)), Kyoto cloth, 120℃1
After drying for 0 minutes, an intermediate layer having a thickness of 0.2 μm was formed.

次にポリビニルブチラール樹脂(XYIIL;ユニオン
カーバイド社製)4重量部をシクロへキサノン150重
量部に溶解し、これに下記構造式(c)に示すジスアゾ
顔料10重量部を力aえボールミルにて48時間分散、
さらにシクロへキサノン210重11.部を加え、3時
間ボールミル分敗を行った。これを容器に取り出し固型
分が1.0重量%になるように撹拌しながらシクロヘキ
サノンで希釈した。こうして得られた電荷発生JVi用
塗布液を前記中間層上に浸漬塗布を行い、120℃で1
0分間乾燥し厚さ0.2μmの電荷発生/Mを設けた。
Next, 4 parts by weight of polyvinyl butyral resin (XYIIL; manufactured by Union Carbide) was dissolved in 150 parts by weight of cyclohexanone, and 10 parts by weight of a disazo pigment represented by the following structural formula (c) was added to the solution by a ball mill for 48 parts by weight. time dispersion,
Furthermore, cyclohexanone 210 weight 11. A ball mill test was performed for 3 hours. This was taken out into a container and diluted with cyclohexanone while stirring so that the solid content was 1.0% by weight. The charge generating JVi coating solution thus obtained was dip coated onto the intermediate layer, and
After drying for 0 minutes, a charge generation/M layer with a thickness of 0.2 μm was provided.

次に,ポリカーボネー1〜樹脂〔パンライトK−130
0(帝人化或社′I3)〕10重量部、シリコンオイル
(KF−50(信越化学工業社製))0.002重量部
をテトラヒド口フラン85重7Iε部に溶解し、これに
下V2構造式(d)に示す電荷輸送物質9重量部と 例示化合物Nalのポリヒドロキシフラバン化合物を0
.09重量部加え溶解して電荷輸送層塗布液を作威した
。これを前記電荷発生層」二に塗布、130℃20分間
乾燥し厚さ20μmの電荷輸送層を形成し,実施例4の
電子写真感光体を作成した。
Next, polycarbonate 1 to resin [Panlite K-130
0 (Teijin Kaisha 'I3)] and 0.002 parts by weight of silicone oil (KF-50 (manufactured by Shin-Etsu Chemical Co., Ltd.)) were dissolved in 85 parts by weight of tetrahydrofuran and 7 parts by weight, and the lower V2 structure was dissolved in this. 9 parts by weight of the charge transport substance shown in formula (d) and the polyhydroxyflavan compound of the exemplary compound Nal were added to 0
.. 09 parts by weight were added and dissolved to prepare a charge transport layer coating solution. This was applied to the charge generation layer 2 and dried at 130° C. for 20 minutes to form a charge transport layer having a thickness of 20 μm, thereby producing an electrophotographic photoreceptor of Example 4.

実施例5,6 実施例4において、例示化合物Nαlの代わりにそれぞ
れ例示化合物Na28,Nα66のポリヒドロキシフラ
バン化合物を用いたほかは実施例4と同様にして実施例
5,6の電子写真感光体を作成した.比較例5 実施例4において、例示化合物Nnlのポリヒドロキシ
フラバン化合物を添加しないほかは実施例4と同様にし
て比較例5の電子写真感光体を作或した。
Examples 5 and 6 Electrophotographic photoreceptors of Examples 5 and 6 were produced in the same manner as in Example 4, except that polyhydroxyflavan compounds of exemplified compounds Na28 and Nα66 were used in place of exemplified compound Nαl, respectively. Created. Comparative Example 5 An electrophotographic photoreceptor of Comparative Example 5 was prepared in the same manner as in Example 4, except that the polyhydroxyflavan compound of exemplified compound Nnl was not added.

比較例6〜8 実施例4において、例示化合物&1のポリヒドロキシフ
ラバン化合物のかわりに前に示した比較化合物1,2.
3を各々0.09重量部添加したほかは実施例4と同様
にして比較例6,7.8の電子写真感光体を作威した。
Comparative Examples 6 to 8 In Example 4, Comparative Compounds 1, 2, .
Electrophotographic photoreceptors of Comparative Examples 6 and 7.8 were produced in the same manner as in Example 4, except that 0.09 parts by weight of each of Comparative Examples 3 and 3 were added.

以上のようにして得られた電子写真感光体の静電特性を
SP−428(川口電機製作所製〉を用い、ダイナミッ
グ方式にて測定した。まず印加電圧−6KVで20秒間
帯電した後20秒間暗減衰、さらに表面照?61uxに
なるようにして30秒間露光を行った.帯電電位は帯電
2秒後の表面電位V2(−V)を、感度は露光後、表面
電位が−800Vから−80Vになるのに要する露光量
E■/■。(1ux−SeC)を、残留電位は露光30
秒後の表面電位を測定した。
The electrostatic properties of the electrophotographic photoreceptor obtained as described above were measured using a dynamic method using SP-428 (manufactured by Kawaguchi Electric Seisakusho).First, it was charged with an applied voltage of -6 KV for 20 seconds, and then darkened for 20 seconds. Exposure was performed for 30 seconds to attenuate and further increase the surface illumination to 61ux.The charging potential was the surface potential V2 (-V) after 2 seconds of charging, and the sensitivity was as the surface potential changed from -800V to -80V after exposure. The exposure amount E■/■.(1ux-SeC) required to
The surface potential was measured after seconds.

その後、色温度2856Kのタングステン光51uスの
光照射、−6KVでの帯電のくり返し疲労を3時間行っ
た後,再び前と同様にしてv, (−v)、E■/1.
(1ux・see)、■,。(一V)を測定した。
Thereafter, after irradiation with 51 μs of tungsten light with a color temperature of 2856K and repeated fatigue of charging at -6KV for 3 hours, the same procedure as before was performed to obtain v, (-v), E■/1.
(1ux・see),■,. (1 V) was measured.

実施例7 実施例1と同様にしてアルミニウム板上に中間層を形或
し、さらに実施例1に示される電荷輸送層塗布液を前記
中間層上に浸漬塗工法により塗布,乾燥し膜Jヴ20μ
mの電荷輸送層を作成した.次にポリカーボネート樹脂
(パンライトL− 1 250、帝人化成社H)to重
量部をテトラヒドロフラン150重量部の混合溶媒に溶
解し、これに前記構造式(a)のトリスアゾ顔料3重量
部を加えボールミルにて48時間分敗を行った。さらに
この分散液に前記構造式(b)に示す電荷輸送物質7重
量部、シクロへキサノン300重量部ボールミルにて2
4時間分敗、溶解し電荷発生層用塗布液を作成した.こ
れを前記電荷輸送層上にスプレー塗布、乾燥して膜J1
3PI1の電荷発生層を設け,電子写真感光体を作成し
た。
Example 7 An intermediate layer was formed on an aluminum plate in the same manner as in Example 1, and the charge transport layer coating solution shown in Example 1 was applied onto the intermediate layer by dip coating and dried to form a film JV. 20μ
A charge transport layer of m was created. Next, two parts by weight of a polycarbonate resin (Panlite L-1 250, Teijin Kasei H) was dissolved in a mixed solvent of 150 parts by weight of tetrahydrofuran, and 3 parts by weight of the trisazo pigment having the structural formula (a) above was added thereto and the mixture was placed in a ball mill. He lost 48 hours. Further, this dispersion was added with 7 parts by weight of the charge transporting substance shown in the structural formula (b) and 300 parts by weight of cyclohexanone in a ball mill.
It was allowed to stand for 4 hours and dissolved to create a coating solution for the charge generation layer. This was spray coated on the charge transport layer and dried to form a film J1.
A charge generation layer of 3PI1 was provided to prepare an electrophotographic photoreceptor.

実施例8 実施例7において、電荷輸送中に含まれる例示化合物I
JQIのポリヒドロキシフラバン化合物のかわりに例示
化合物No2gのポリヒドロキシフラバン化合物を用い
た他は実施例7と同様にして実施例8の電子写真感光体
を作成した。
Example 8 In Example 7, exemplary compound I included in charge transport
An electrophotographic photoreceptor of Example 8 was prepared in the same manner as in Example 7 except that the polyhydroxyflavan compound of Exemplary Compound No. 2g was used instead of the polyhydroxyflavan compound of JQI.

比較例9 実施例7において、電荷輸送層中に含まれる例示化合物
&lのポリヒドロキシフラバン化合物を除いたほかは実
施例7と同様にして比較例9の電子写真感光体を作或し
た。
Comparative Example 9 An electrophotographic photoreceptor of Comparative Example 9 was prepared in the same manner as in Example 7 except that the polyhydroxyflavan compound of the exemplified compound &l contained in the charge transport layer was removed.

比較例10.11 実施例7において、電荷輸送層中に含まれる例示化合物
Nαlのポリヒドロキシフラバン化合物の代わりにそれ
ぞれ前記比較化合物1.3を各々0.07重量部添加し
たほかは実施例7と同様にして比較例10.11の電子
写真感光体を作威した.以上のようにして得られた実施
例7,8,比較例9,10. 11の静電特性は帯電の
印加電圧を+6KVに電位の評価をプラスで行った以外
は実施例lの電子写真感光体の評価方法と同様の方法に
て評価を行った。
Comparative Example 10.11 Example 7 except that 0.07 parts by weight of Comparative Compound 1.3 was added in place of the polyhydroxyflavan compound of the exemplified compound Nαl contained in the charge transport layer. Electrophotographic photoreceptors of Comparative Example 10.11 were produced in the same manner. Examples 7 and 8 and Comparative Examples 9 and 10 obtained as above. The electrostatic properties of Sample No. 11 were evaluated in the same manner as the evaluation method of the electrophotographic photoreceptor of Example 1, except that the applied voltage for charging was +6 KV and the potential was evaluated as positive.

評価結果を表−2に示す.The evaluation results are shown in Table 2.

Claims (1)

【特許請求の範囲】[Claims] (1)導電性支持体上に電荷発生物質と電荷輸送物質と
を含有する感光層を有する電子写真感光体において、前
記感光層中に下記一般式〔 I 〕に示すポリヒドロキシ
フラバン化合物を含有することを特徴とする電子写真感
光体。 ▲数式、化学式、表等があります▼( I ) (式中、R_1〜R_7はそれぞれ、水素原子、ヒドロ
キシ基、ハロゲン原子、アルキル基、アルケニル基、ア
リール基、シクロアルキル基、アルコキシ基、置換アミ
ノ基、イミノ基、複素環基、アルキルキオ基又はアシル
基を表わす、但し、R_3〜R_7のうち少なくとも一
つは、ヒドロキシ基である。)
(1) In an electrophotographic photoreceptor having a photosensitive layer containing a charge generating substance and a charge transporting substance on a conductive support, the photosensitive layer contains a polyhydroxyflavan compound represented by the following general formula [I]. An electrophotographic photoreceptor characterized by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R_1 to R_7 are each a hydrogen atom, hydroxy group, halogen atom, alkyl group, alkenyl group, aryl group, cycloalkyl group, alkoxy group, substituted amino group, imino group, heterocyclic group, alkylkio group, or acyl group, provided that at least one of R_3 to R_7 is a hydroxy group.)
JP23955789A 1989-09-14 1989-09-14 Electrophotographic sensitive body Pending JPH03101738A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP23955789A JPH03101738A (en) 1989-09-14 1989-09-14 Electrophotographic sensitive body

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP23955789A JPH03101738A (en) 1989-09-14 1989-09-14 Electrophotographic sensitive body

Publications (1)

Publication Number Publication Date
JPH03101738A true JPH03101738A (en) 1991-04-26

Family

ID=17046572

Family Applications (1)

Application Number Title Priority Date Filing Date
JP23955789A Pending JPH03101738A (en) 1989-09-14 1989-09-14 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPH03101738A (en)

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Publication number Priority date Publication date Assignee Title
JP2014126797A (en) * 2012-12-27 2014-07-07 Canon Inc Charging member, process cartridge, and electrophotographic image forming apparatus
US20140221183A1 (en) * 2012-12-27 2014-08-07 Canon Kabushiki Kaisha Charging member, process cartridge, and electrophotographic image forming apparatus
CN104885018A (en) * 2012-12-27 2015-09-02 佳能株式会社 Charging member, processing cartridge, and electrophotographic image forming apparatus
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