JPH01136161A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPH01136161A
JPH01136161A JP29644787A JP29644787A JPH01136161A JP H01136161 A JPH01136161 A JP H01136161A JP 29644787 A JP29644787 A JP 29644787A JP 29644787 A JP29644787 A JP 29644787A JP H01136161 A JPH01136161 A JP H01136161A
Authority
JP
Japan
Prior art keywords
group
charge
formula
charge transport
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.)
Granted
Application number
JP29644787A
Other languages
Japanese (ja)
Other versions
JPH0549227B2 (en
Inventor
Masakazu Matsumoto
正和 松本
Shozo Ishikawa
石川　昌三
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.)
Canon Inc
Original Assignee
Canon Inc
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 Canon Inc filed Critical Canon Inc
Priority to JP29644787A priority Critical patent/JPH01136161A/en
Priority to US07/274,503 priority patent/US4931371A/en
Priority to FR8815260A priority patent/FR2623638B1/en
Publication of JPH01136161A publication Critical patent/JPH01136161A/en
Publication of JPH0549227B2 publication Critical patent/JPH0549227B2/ja
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/062—Acyclic or carbocyclic compounds containing non-metal elements other than hydrogen, halogen, oxygen or nitrogen
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0629—Heterocyclic compounds containing one hetero ring being five-membered containing one hetero atom
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0631—Heterocyclic compounds containing one hetero ring being five-membered containing two hetero atoms
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0633—Heterocyclic compounds containing one hetero ring being five-membered containing three hetero atoms
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
    • G03G5/0637—Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
    • G03G5/0638—Heterocyclic compounds containing one hetero ring being six-membered containing two hetero atoms
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
    • G03G5/064—Heterocyclic compounds containing one hetero ring being six-membered containing three hetero atoms
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0624—Heterocyclic compounds containing one hetero ring
    • G03G5/0642—Heterocyclic compounds containing one hetero ring being more than six-membered
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0698—Compounds of unspecified structure characterised by a substituent only

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

PURPOSE:To obtain an electrophotographic sensitive body having high sensitivity and causing less fluctuation of potential even if repetitive electric charge and exposure are applied for a long time by incorporating a specified compd. into a photosensitive layer. CONSTITUTION:A disubstituted aminoaryl group expressed by formula I, a linear sulfide structure expressed by formula II, and a linear sulfide structure expressed by formula III are both contained in the structural formula of the above described compd., which is contained in a photosensitive layer. In formulas, each R1 and R2 is a (substituted)alkyl group or a residue necessary for forming a 5- or 6-membered ring by the combination of R1 and R2; Ar is a (substituted)arylene group; R3 is a (substituted)aryl group; R4 is a (substituted) alkyl or aralkyl group. By this constitution, an electrophotographic sensitive body having high sensitivity and causing slight fluctuation of potentials in a light zone and dark zone due to repetitive electric charge or exposure for a long time during the formation of continuous picture image is obtd.

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、電子写真感光体に関し、詳しくは改善された
電子写真特性を与える低分子の有機光導電体を有する電
子写真感光体に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a low molecular weight organic photoconductor that provides improved electrophotographic properties. be.

〔従来技術〕[Prior art]

従来、電子写真感光体で用いる光導電材料として、ポリ
ビニルカルバゾールをはじめとする各種の有機光導電性
ポリマーが提案されて来たが、これらのポリマーは、無
機系光導電材料に較べ成膜性、軽量性などの点で優れて
いるにもかかわらず今日までその実用化が困難であった
のは、未だ十分な成膜性が得られておらず、また感度、
耐久性および環境変化による安定性の点で無機系光導電
材料に較べ劣っているためであった。また、米国特許第
４１５０９８７号公報などに開示のヒドラゾン化合物、
米国特許第３８３７８５１号公報などに記載のトリアリ
ールピラゾリン化合物、特開昭５１−９４８２８号公報
、特開昭５１−９４８２９号公報などに記載の９−スチ
リルアントラセン化合物などの低分子の有機光導電体が
提案されている。この様な低分子の有機光導電体は、使
用するバインダーを適当に選択することによって、有機
光導電性ポリマーの分野で問題となっていた成膜性の欠
点を解消できる様になったが、感度の点で十分なものと
は言えない。Conventionally, various organic photoconductive polymers including polyvinyl carbazole have been proposed as photoconductive materials for use in electrophotographic photoreceptors, but these polymers have poor film formability and poor film formability compared to inorganic photoconductive materials. Although it is excellent in terms of lightness and other aspects, it has been difficult to put it into practical use until now because sufficient film formation properties have not yet been obtained, and sensitivity and
This is because they are inferior to inorganic photoconductive materials in terms of durability and stability against environmental changes. In addition, hydrazone compounds disclosed in US Pat. No. 4,150,987, etc.
Low-molecular organic photoconductive compounds such as triarylpyrazoline compounds described in U.S. Pat. body is proposed. By appropriately selecting the binder used, such low-molecular-weight organic photoconductors can overcome the drawbacks of film-forming properties that had been a problem in the field of organic photoconductive polymers. It cannot be said that the sensitivity is sufficient.

このようなことから、近年感光層を電荷発生層と電荷輸
送層に機能分離させた積層構造体が提案された。この積
層構造を感光層とした電子写真感光体は、可視光に対す
る感度、電荷保持力、表面強度などの点で改善できるよ
うになった。この様な電子写真感光体は、例えば米国特
許第３，８３７，８５１号、同第３，８７１，８８２号
公報などに開示されている。For these reasons, a laminated structure in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer has been proposed in recent years. Electrophotographic photoreceptors using this laminated structure as a photosensitive layer can now be improved in terms of sensitivity to visible light, charge retention, surface strength, and the like. Such electrophotographic photoreceptors are disclosed, for example, in US Pat. No. 3,837,851 and US Pat. No. 3,871,882.

しかし、従来の低分子の有機光導電体を電荷輸送層に用
いた電子写真感光体では、感度、特性が、実用レベルに
達していても、繰り返し帯電および露光を行なった際に
は明部電位と暗部電位の変動が大きいという欠陥は十分
に解決されていない。However, in electrophotographic photoreceptors that use conventional low-molecular-weight organic photoconductors in the charge transport layer, even if their sensitivity and characteristics have reached a practical level, the light area potential decreases when repeatedly charged and exposed. The drawback of large fluctuations in the dark potential has not been sufficiently resolved.

この繰り返し使用時における電位の変動を抑えるため、
例えば特開昭５７−１２２４４４号、特開昭６２−３９
８６３号には電荷輸送層中に酸化防止剤を混在せしめる
方法が開示されており、他にも特開昭５３−２６１２８
号、特開昭６０−１６４７４５号、特開昭６２−１０５
１５１号等によれば添加剤を加えて安定化させる方法が
知られている。しかし、これらの方法では特に繰り返し
使用が長期にわたる時は効果が十分でないのが現状であ
る。In order to suppress potential fluctuations during repeated use,
For example, JP-A-57-122444, JP-A-62-39
No. 863 discloses a method of mixing an antioxidant in a charge transport layer, and Japanese Patent Application Laid-Open No. 53-26128 discloses a method of mixing an antioxidant into a charge transport layer.
No., JP-A-60-164745, JP-A-62-105
According to No. 151, etc., a method of stabilizing by adding additives is known. However, the current situation is that these methods are not sufficiently effective, especially when repeatedly used over a long period of time.

〔発明が解決しようとする問題点〕[Problem that the invention seeks to solve]

本発明の目的は、前述の欠点又は不利を解消した電子写
真感光体を提供することにある。An object of the present invention is to provide an electrophotographic photoreceptor that eliminates the above-mentioned drawbacks or disadvantages.

本発明の別の目的は、繰り返し使用にあたって安定な有
機光導電体を提供することにある。Another object of the present invention is to provide an organic photoconductor that is stable upon repeated use.

〔問題点を解決するための手段〕[Means for solving problems]

すなわち、本発明は、導電性支持体上に感光層を有する
電子写真感光体において、構造式中に、一般式（Ｉ） で示されるジ置換アミノアリール基と、一般式（ｎ） −３−Ｒ３・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・　（ＩＩ）で示され
る鎖状スルフィド構造と、 一般式（ｍ） −５−Ｒ４・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・　（ｍ）で示される
鎖状スルフィド構造とを併せ持った化合物を感光層中に
含有することを特徴とする電子写真感光体である。That is, the present invention provides an electrophotographic photoreceptor having a photosensitive layer on a conductive support, in which the structural formula includes a disubstituted aminoaryl group represented by the general formula (I) and a general formula (n) -3- R3・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・ Chain sulfide structure represented by (II) and general formula (m) -5-R4・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・ An electrophotographic photoreceptor characterized by containing a compound having a chain sulfide structure represented by (m) in a photosensitive layer.

式中、Ｒ１およびＲ２は、メチル、エチル、プロピル、
ブチル等のアルキル基、フェニル、ナフチル、アンスリ
ル、ビフェニル等のアリール基、ベンジル、フェネチル
、ナフチルメチル等のアラルキル基、または、Ｒ１とＲ
２で結合してピロリジノ。In the formula, R1 and R2 are methyl, ethyl, propyl,
Alkyl groups such as butyl, aryl groups such as phenyl, naphthyl, anthryl, biphenyl, aralkyl groups such as benzyl, phenethyl, naphthylmethyl, or R1 and R
Combined with 2 to form pyrrolidino.

ピペリジノ、モルホリノ等の５ないし６員環の環状アミ
ノ基を形成するのに必要な残基を示す。Residues necessary to form a 5- to 6-membered cyclic amino group such as piperidino and morpholino are shown.

Ａｒは、フェニレン、ナフチレン、ビフェニレン。Ar is phenylene, naphthylene, or biphenylene.

アンスリレン等のアリーレン基を示す。Indicates an arylene group such as anthrylene.

Ｒ３はフェニル、ナフチル、ビフェニル等のアリール基
を示す。R3 represents an aryl group such as phenyl, naphthyl, or biphenyl.

Ｒ４は、メチル、エチル、プロピル、ブチル等のアルキ
ル基、フェニル、ナフチル、アンスリル。R4 is an alkyl group such as methyl, ethyl, propyl, butyl, phenyl, naphthyl, anthryl.

ビフェニル等のアリール基、またはベンジル、フェネチ
ル、ナフチルメチル等のアラルキル基を示す。It represents an aryl group such as biphenyl, or an aralkyl group such as benzyl, phenethyl, naphthylmethyl.

また、Ｒ１＋　Ｒ２＋　”＋　Ｒ３およびＲ４で示した
基は、置換基を有してもよ（、これらの置換基としては
、メチル、エチル、ブチル等のアルキル基、メトキシ、
エトキシ、プロポキシ等のアルコキシ基、ベンジル、フ
ェネチル、ナフチルメチル等のアラルキル基、フッ素、
塩素、臭素、沃素等のハロゲン原子、水酸基、またはメ
ルカプト基が挙げられる。Furthermore, the groups represented by R1+ R2+ ''+ R3 and R4 may have substituents (these substituents include alkyl groups such as methyl, ethyl, butyl, methoxy,
Alkoxy groups such as ethoxy and propoxy, aralkyl groups such as benzyl, phenethyl and naphthylmethyl, fluorine,
Examples include halogen atoms such as chlorine, bromine, and iodine, hydroxyl groups, and mercapto groups.

本発明になる化合物は上記ジ置換アミノアリール基とア
リール置換鎖状スルフィド構造と鎖状スルフィド構造部
分とを結合せしめて構成されるが、その結合の手段は特
定されない。即ち、２つの構造部分を直接結合しても、
共役又は非共役の有機基によって結合しても、更にはア
リール部分等を共有した形で結合していてもすぐれた効
果を発現するものである。要はジ置換アミノアリール基
とアリール置換鎖状スルフィド構造と鎖状スルフィド構
造部分が同一分子中に共存していれば良い。The compound of the present invention is constructed by bonding the disubstituted aminoaryl group, the aryl-substituted chain sulfide structure, and the chain sulfide structure moiety, but the means of bonding is not specified. That is, even if two structural parts are directly connected,
Even if they are bonded through a conjugated or non-conjugated organic group, or even if they are bonded through a covalent aryl moiety, excellent effects can be obtained. In short, it is sufficient that the disubstituted aminoaryl group, the aryl-substituted chain sulfide structure, and the chain sulfide structure moiety coexist in the same molecule.

この構造が繰り返しによる特性劣化に対し特異的に良好
な効果を示す理由は定かではないが、オゾン、ＮＯｘ、
硝酸等複写機の機内で発生する環境劣化因子に対してジ
置換アミノアリール基のＮの塩基性とスルフィドの硫黄
原子のｄ軌道効果とが相乗的に働き、環境劣化因子の浸
透を妨げているものと考えられる。It is not clear why this structure has a uniquely good effect on characteristic deterioration due to repeated use, but it
The basicity of N in the di-substituted aminoaryl group and the d-orbital effect of the sulfur atom of the sulfide act synergistically against environmental deterioration factors generated inside copying machines, such as nitric acid, and prevent the penetration of environmental deterioration factors. considered to be a thing.

アリール置換鎖状スルフィド構造１ケ所のみでは十分な
効果が得られない。これは、アルキルチオ基。A sufficient effect cannot be obtained with only one aryl-substituted chain sulfide structure. This is an alkylthio group.

アラルキルチオ基が電子供与性基の影響で硫黄原子がか
なり活性化されているのに対して、アリールチオ基では
アリール基の影響で硫黄原子の活性度が前２者に比べ低
下している為と思われる。従って、スルフィド構造は更
に１ケ所以上必要である。This is because the sulfur atom of the aralkylthio group is considerably activated due to the influence of the electron-donating group, whereas the activity of the sulfur atom of the arylthio group is lower than that of the former two due to the influence of the aryl group. Seem. Therefore, one or more additional sulfide structures are required.

以下に本発明になる化合物についてその代表例を挙げる
。Representative examples of the compounds of the present invention are listed below.

く化合物例〉 １９゜ し１′ｉ３ ３４゜ ３５゜ 本発明になる化合物は構造式によって合成ルートは異な
るものの一般的なスルフィド、３級アミンの合成法また
はその類似法によって合成される。Examples of Compounds> 19° and 1'i3 34° 35° The compounds of the present invention can be synthesized by a general method for synthesizing sulfides or tertiary amines or similar methods, although the synthetic route varies depending on the structural formula.

本発明になる化合物は電荷発生層と電荷輸送層を積層し
た層分離型感光層の電荷発生層または電荷輸送層に含有
させることにより、効果を示すものであり、特に感光層
中の電荷輸送物質に対して著しい効果を表わす。The compound of the present invention exhibits effects when incorporated into the charge generation layer or the charge transport layer of a layer-separated photosensitive layer in which a charge generation layer and a charge transport layer are laminated. shows a remarkable effect on

また、本発明になる化合物はそれ自体で電荷輸送物質と
してのキャリア搬送性を有しているものも多（。後述の
ような他の電荷輸送物質と混合せず単独に用いても構わ
ない。本発明になる電子写真感光体の構成について、以
下に詳述する。In addition, many of the compounds of the present invention have carrier transport properties as charge transport substances by themselves (although they may be used alone without being mixed with other charge transport substances as described below). The structure of the electrophotographic photoreceptor according to the present invention will be described in detail below.

本発明になる化合物と共に用いられる電荷輸送物質とし
ては、有機の電子輸送性物質と正孔輸送性物質があり、
電子輸送性物質としては、クロルアニル、ブロモアニル
、テトラシアノエチレン、テトラシアノキノジメタン、
２，４．７−）ジニトロ−９−フルオレノン、２．　４
．　５．　７−テトラニトロ−９−フルオレノン、２，
４．７−）リニトロー９−ジシアノメチレンフルオレノ
ン、２．　４．　５．　７−チトラニトロキサントン、
２，４．８−トリニドロチオキサントン等の電子吸引性
物質やこれら電子吸引性物質を高分子化したもの等があ
る。Charge transporting substances used with the compound of the present invention include organic electron transporting substances and hole transporting substances.
Examples of electron transporting substances include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane,
2,4.7-) dinitro-9-fluorenone, 2. 4
．． 5. 7-tetranitro-9-fluorenone, 2,
4.7-) Rinitro 9-dicyanomethylenefluorenone, 2. 4. 5. 7-titranitroxanthone,
Examples include electron-withdrawing substances such as 2,4,8-trinidrothioxanthone, and polymerization of these electron-withdrawing substances.

正孔輸送性物質としては、ピレン、Ｎ−エチルカルバゾ
ール、Ｎ−イソプロピルカルバゾール、Ｎ−メチル−Ｎ
−フェニルヒドラジノ−３−メチリデン−９−エチルカ
ルバゾール、Ｎ、Ｎ−ジフェニルヒドラジノ−３−メチ
リデン−９−エチルカルバゾール、Ｎ、Ｎ−ジフェニル
ヒドラジノ−３−メチリデン−１０−エチルフェノチア
ジン、Ｎ、Ｎ−ジフェニルヒドラジノ−３−メチリデン
−１０−二チルフエノキサジン、ｐ−ジエチルアミノベ
ンズアルデヒド−Ｎ、Ｎ−ジフェニルヒドラゾン、ｐ−
ジエチルアミノベンズアルデヒド−Ｎ−α−ナフチル−
Ｎ−フェニルヒドラゾン、ｐ−ピロリジノベンズアルデ
ヒド−Ｎ、Ｎ−ジフェニルヒドラゾン、１，３゜３−ト
リメチルインドレニン−ω−アルデヒド−Ｎ。Examples of hole transporting substances include pyrene, N-ethylcarbazole, N-isopropylcarbazole, N-methyl-N
-Phenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-10-ethylphenothiazine, N, N-diphenylhydrazino-3-methylidene-10-ditylphenoxazine, p-diethylaminobenzaldehyde-N,N-diphenylhydrazone, p-
Diethylaminobenzaldehyde-N-α-naphthyl-
N-phenylhydrazone, p-pyrrolidinobenzaldehyde-N, N-diphenylhydrazone, 1,3°3-trimethylindolenine-ω-aldehyde-N.

Ｎ−ジフェニルヒドラゾン、ｐ−ジエチルベンズアルデ
ヒド−３−メチルベンズチアゾリン−２−ヒドラゾン等
のヒドラゾン類、２．５−ビス（ｐ−ジエチルアミノフ
ェニル）　−１，３，４−オキサジアゾール、１−フェ
ニル−３−（ｐ−ジエチルアミノスチリル）−５−（ｐ
−ジエチルアミノフェニル）ピラゾリン、１−（キノリ
ル（２））−３−（ｐ−ジエチルアミノスチリル）−５
−（ｐ−ジエチルアミノフェニル）ピラゾリン、１−〔
ピリジル（２））−３−（ｐ−ジエチルアミノスチリル
）−５−（ｐ−ジエチルアミノフェニル）ピラゾリン、
１−　（６−メドキシーピリジル（２））−３−（ｐ−
ジエチルアミノスチリル）−５−（ｐ−ジエチルアミノ
フェニル）ピラゾリン、１−〔ピリジル（３））−３−
（ｐ−ジエチルアミノスチリル）−５−（ｐ−ジエチル
アミノフェニル）ピラゾリン、１−〔レピジル（２））
　−３−（ｐ−ジエチルアミノスチリル）−５−（ｐ−
ジエチルアミノフェニル）ピラゾリン、ｌ−〔ピリジル
（２））−３−（ｐ−ジエチルアミノスチリル）−４−
メチル−５−（ｐ−ジエチルアミノフェニル）ピラゾリ
ン、１−〔ピリジル（２））−３−（α−メチル−ｐ−
ジエチルアミノスチリル）−５−（ｐ−ジエチルアミノ
フェニル）ピラゾリン、ｌ−フェニル−３−（ｐ−ジエ
チルアミノステリル）−４−メチル−５−（ｐ−ジエチ
ルアミノフェニル）ピラゾリン、ｌ−フェニル−３−（
α−ベンジル−ｐ−ジエチルアミノスチリル）−５−（
ｐ−ジエチルアミノフェニル）ピラゾリン、スピロピラ
ゾリンなどのピラゾリン類、α−フェニル−４−Ｎ、Ｎ
−ジフェニルアミノスチルベン、Ｎ−エチル−３（α−
フェニルスチリル）カルバゾール、９−ｐ−ジベンジル
アミノベンジリデン−９Ｈ−フルオレノン、５−ｐ−ジ
トリルアミノベンジリデン−５Ｈ−ジベンゾ（ａｔｄ〕
シクロヘプテン等のスチリル系化合物類、２−（ｐ−ジ
エチルアミノスチリル）−６−ジニチルアミノベンズオ
キサゾール、２−（ｐ−ジエチルアミノフェニル）−４
−（ｐ−ジメチルアミノフェニル）−５−（２−クロロ
フェニル）オキサゾール等のオキサゾール系化合物、２
−（ｐ−ジエチルアミノスチリル）−６−ジニチルアミ
ノベンゾチアゾール等のチアゾール系化合物、ビス（４
−ジエチルアミノ−２−メチルフェニル）−フェニルメ
タン等のトリアリールメタン系化合物、１．　１−ビス
（４−Ｎ。Hydrazones such as N-diphenylhydrazone, p-diethylbenzaldehyde-3-methylbenzthiazoline-2-hydrazone, 2,5-bis(p-diethylaminophenyl)-1,3,4-oxadiazole, 1-phenyl- 3-(p-diethylaminostyryl)-5-(p
-diethylaminophenyl)pyrazoline, 1-(quinolyl(2))-3-(p-diethylaminostyryl)-5
-(p-diethylaminophenyl)pyrazoline, 1-[
pyridyl (2))-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline,
1-(6-medoxypyridyl(2))-3-(p-
diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[pyridyl(3))-3-
(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[Lepidil (2))
-3-(p-diethylaminostyryl)-5-(p-
diethylaminophenyl)pyrazoline, l-[pyridyl(2))-3-(p-diethylaminostyryl)-4-
Methyl-5-(p-diethylaminophenyl)pyrazoline, 1-[pyridyl(2))-3-(α-methyl-p-
diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, l-phenyl-3-(p-diethylaminosteryl)-4-methyl-5-(p-diethylaminophenyl)pyrazoline, l-phenyl-3-(
α-benzyl-p-diethylaminostyryl)-5-(
Pyrazolines such as p-diethylaminophenyl) pyrazoline and spiropyrazoline, α-phenyl-4-N, N
-diphenylaminostilbene, N-ethyl-3(α-
phenylstyryl) carbazole, 9-p-dibenzylaminobenzylidene-9H-fluorenone, 5-p-ditolylaminobenzylidene-5H-dibenzo(atd)
Styryl compounds such as cycloheptene, 2-(p-diethylaminostyryl)-6-dinithylaminobenzoxazole, 2-(p-diethylaminophenyl)-4
-(p-dimethylaminophenyl)-5-(2-chlorophenyl)oxazole and other oxazole compounds, 2
-(p-diethylaminostyryl)-6-dinithylaminobenzothiazole and other thiazole compounds, bis(4
Triarylmethane compounds such as -diethylamino-2-methylphenyl)-phenylmethane, 1. 1-bis(4-N.

Ｎ−ジエチルアミノ−２−メチルフェニル）へブタン、
ｌ、　　１．２．２−テトラキス（４−Ｎ、Ｎ−ジメチ
ルアミノ−２−メチルフェニル）エタン等のポリアリー
ルアルカン類、トリフェニルアミン、ポリ−Ｎ−ビニル
カルバゾール、ポリビニルピレン、ポリビニルアントラ
セン、ポリビニルアクリジン、ポリ−９−ビニルフェニ
ルアントラセン、ピレン−ホルムアルデヒド樹脂、エチ
ルカルバゾールホルムアルデヒド樹脂等がある。N-diethylamino-2-methylphenyl)hebutane,
1.2. Polyarylalkanes such as 2-tetrakis(4-N,N-dimethylamino-2-methylphenyl)ethane, triphenylamine, poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinyl Examples include acridine, poly-9-vinylphenylanthracene, pyrene-formaldehyde resin, and ethylcarbazole formaldehyde resin.

これらの電荷輸送物質は、１種または２種以上組合わせ
て用いることができる。These charge transport substances can be used alone or in combination of two or more.

本発明による層分離型電子写真感光体における電荷輸送
層は、前記の構造式中にジ置換アミノアリール基とスル
フィド構造とを併せ持つ化合物を前記の電荷輸送物質と
結着剤と共に適当な溶剤に溶解せしめた溶液を塗布し、
乾燥せしめることにより形成させることが好ましい。前
述の如く、本発明になる化合物が電荷輸送物質としての
機能を有する場合は単に結着剤と共に用いてもよい。こ
こに用いる結着剤としては、例えばボリアリレート樹脂
、ポリスルホン樹脂、ポリアミド樹脂、アクリル樹脂、
アクリロニトリル樹脂、メタクリル樹脂、塩化ビニル樹
脂、酢酸ビニル樹脂、フェノール樹脂、エポキシ樹脂、
ポリエステル樹脂、アルキド樹脂、ポリカーボネート、
ポリウレタンあるいは共重合体樹脂例えばスチレン−ブ
タジェンコポリマー、スチレン−アクリロニトリルコポ
リマー、スチレン−マレイン酸コポリマーなどを挙げる
ことができる。また、このような絶縁性ポリマーの他に
、ポリビニルカルバゾール、ポリビニルアントラセンや
ポリビニルピレンなどの有機光導電性ポリマーも使用で
きる。The charge transport layer in the layer-separated electrophotographic photoreceptor according to the present invention includes a compound having both a disubstituted aminoaryl group and a sulfide structure in the above structural formula, which is dissolved in an appropriate solvent together with the above charge transport substance and binder. Apply a damp solution,
Preferably, it is formed by drying. As mentioned above, when the compound of the present invention has a function as a charge transport substance, it may be used simply together with a binder. Examples of the binder used here include polyarylate resin, polysulfone resin, polyamide resin, acrylic resin,
Acrylonitrile resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, phenolic resin, epoxy resin,
polyester resin, alkyd resin, polycarbonate,
Examples of polyurethane or copolymer resins include styrene-butadiene copolymers, styrene-acrylonitrile copolymers, styrene-maleic acid copolymers, and the like. In addition to such insulating polymers, organic photoconductive polymers such as polyvinylcarbazole, polyvinylanthracene, and polyvinylpyrene can also be used.

この結着剤と電荷輸送物質との配合割合は、結着剤１０
０重量部当り電荷輸送物質を１０〜５００重量とするこ
とが好ましい。The blending ratio of the binder and the charge transport material is 10 parts of the binder.
Preferably, the amount of charge transport material is 10 to 500 parts by weight per 0 parts by weight.

電荷輸送層は、上述の電荷発生層と電気的に接続されて
おり、電界の存在下で電荷発生層から注入された電荷キ
ャリアを受けとるとともに、これらの電荷キャリアを表
面まで輸送できる機能を有している。この際、この電荷
輸送層は、電荷発生層の上に積層されていてもよく、ま
たその下に積層されていてもよい。しかし、電荷輸送層
は、電荷発生層の上に積層されていることが望ましい。The charge transport layer is electrically connected to the charge generation layer described above, and has the function of receiving charge carriers injected from the charge generation layer in the presence of an electric field and transporting these charge carriers to the surface. ing. At this time, this charge transport layer may be laminated on or under the charge generation layer. However, it is desirable that the charge transport layer is laminated on the charge generation layer.

この電荷輸送層は、電荷キャリアを輸送できる限界があ
るので、必要以上に膜厚を厚（することができない。一
般的には、５μｍ〜４０μｍであるが、好ましい範囲は
１０μｍ〜３０μｍである。This charge transport layer cannot be made thicker than necessary because there is a limit to its ability to transport charge carriers. Generally, the thickness is 5 μm to 40 μm, but the preferred range is 10 μm to 30 μm.

この様な電荷輸送層を形成する際に用いる有機溶剤は、
使用する結着剤の種類によって異なり、又は電荷発生層
や上述の下引層を溶解しないものから選択することが好
ましい。具体的な有機溶剤としては、メタノール、エタ
ノール、インプロパツールなどのアルコール類、アセト
ン、メチルエチルケトン、シクロヘキサノンなどのケト
ン類、Ｎ、Ｎ＝ニジメチルホルムアミドＮ、Ｎ−ジメチ
ルアセトアミドなどのアミド類、ジメチルスルホキシド
などのスルホキシド類、テトラヒドロフラン、ジオキサ
ン、エチレングリコールモノメチルエーテルなどのエー
テル類、酢酸メチル、酢酸エチルなどのエステル類、ク
ロロホルム、塩化メチレン、ジクロルエチレン、四塩化
炭素、トリクロルエチレンなどの脂肪族ハロゲン化炭化
水素類あるいはベンゼン、トルエン、キシレン、モノク
ロルベンゼン、ジクロルベンゼンなどの芳香族類などを
用いることができる。The organic solvent used when forming such a charge transport layer is
The binder varies depending on the type of binder used, and it is preferable to select one that does not dissolve the charge generation layer or the above-mentioned subbing layer. Specific organic solvents include alcohols such as methanol, ethanol, and impropatol, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, amides such as N, N=nidimethylformamide, N-dimethylacetamide, and dimethyl sulfoxide. Sulfoxides such as tetrahydrofuran, dioxane, ethers such as ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate, aliphatic halogenated carbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, trichlorethylene, etc. Hydrogens or aromatics such as benzene, toluene, xylene, monochlorobenzene, dichlorobenzene, etc. can be used.

塗工は、浸漬コーティング法、スプレーコーティング法
、マイヤーバーコーティング法、ブレードコーティング
法などのコーティング法を用いて行なうことができる。Coating can be carried out using a coating method such as a dip coating method, a spray coating method, a Meyer bar coating method, or a blade coating method.

乾燥は、室温における指触乾燥後、加熱乾燥する方法が
好ましい。加熱乾燥は、一般的には３０°Ｃ〜２００°
Ｃの温度で５分〜２時間の範囲の時間で、静止または送
風下で行なうことが好ましい。For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying is generally done at 30°C to 200°C.
It is preferable to carry out the reaction at a temperature of 5 minutes to 2 hours at a temperature of 100°C, either stationary or under ventilation.

電荷輸送層には、種々の添加剤を含有させて用いること
もできる。例えば、ジフェニル、ｍ−ターフェニル、ジ
ブチルフタレートなどの可塑剤、シリコンオイル、グラ
フト型シリコンポリマー、各種フルオロカーボン類など
の表面潤滑剤などを挙げることができる。The charge transport layer can also contain various additives. Examples include plasticizers such as diphenyl, m-terphenyl, and dibutyl phthalate, surface lubricants such as silicone oil, grafted silicone polymers, and various fluorocarbons.

本発明で用いる電荷発生層は、セレン、セレン−テルル
、アモルファスシリコン等の無機の電荷発生物質、ピリ
リウム系染料、チアピリリウム系染料、アズレニウム系
染料、チアシアニン系染料、キノシアニン系染料、アズ
レニウム系染料等のカチオン染料、スクバリリウム塩系
染料、フタロシアニン系顔料、アントアントロン系顔料
、ジベンズピレンキノン系顔料、ビラントロン系顔料等
の多環キノン顔料、インジゴ系顔料、キナクリドン系顔
料、アゾ顔料等の有機の電荷発生物質から選ばれた材料
を単独ないしは組み合わせて用い蒸着層あるいは塗布層
として用いることができる。The charge generation layer used in the present invention is made of inorganic charge generation substances such as selenium, selenium-tellurium, amorphous silicon, pyrylium dyes, thiapyrylium dyes, azulenium dyes, thiacyanine dyes, quinocyanine dyes, azulenium dyes, etc. Organic charge generation such as cationic dyes, squbarium salt dyes, phthalocyanine pigments, anthorone pigments, dibenzpyrenequinone pigments, polycyclic quinone pigments such as vilanthrone pigments, indigo pigments, quinacridone pigments, azo pigments, etc. Materials selected from among the substances can be used alone or in combination as a vapor deposited layer or a coating layer.

本発明に使用される上記電荷発生物質のうち、特にアゾ
顔料は多岐にわたっているが、特に効果の高いアゾ顔料
の代表的構造例を以下に示す。Among the charge-generating substances used in the present invention, there are a wide variety of azo pigments in particular, and typical structural examples of particularly effective azo pigments are shown below.

アゾ顔料の一般式として、下記のように中心骨格をＡ。The general formula of an azo pigment is as shown below, with the central skeleton being A.

Ａ千Ｎ＝Ｎ−Ｃｐ）　ｎ カプラ一部分をＣｐとして表わせば（ここでｎ＝２゜ｏ
ｒ３）、まずＡの具体例としては次のようなものが挙げ
られる。A1000N=N-Cp) n If we express part of the coupler as Cp (here n=2゜o
r3), first, specific examples of A include the following.

２Ｈ５ また、Ｃｐの具体例としては （Ｒ：アルキル、アリール等） 等が挙げられる。これら中心骨格Ａ及びカプラーＣｐは
適宜組合せにより電荷発生物質となる顔料を形成する。2H5 Further, specific examples of Cp include (R: alkyl, aryl, etc.). The central skeleton A and the coupler Cp form a pigment serving as a charge-generating substance by appropriate combination.

電荷発生層は、前述の電荷発生物質を適当な結着剤に分
散させ、これを支持体の上に塗工することによって形成
でき、また、真空蒸着装置により蒸着膜を形成すること
によって得ることができる。The charge-generating layer can be formed by dispersing the above-mentioned charge-generating substance in a suitable binder and coating it on a support, or can be obtained by forming a vapor-deposited film using a vacuum evaporation device. Can be done.

上記結着剤としては広範な絶縁性樹脂から選択でき、ま
た、ポリ−Ｎ−ビニルカルバゾール、ポリビニルアント
ラセンやポリビニルピレンなどの有機光導電性ポリマー
から選択できる。好ましくは、ポリビニルブチラール、
ボリアリレート（ビスフェノールＡとフタル酸の縮重合
体など）、ポリカーボネート、ポリエステル、フェノキ
シ樹脂、ポリ酢酸ビニル、アクリル樹脂、ポリアクリル
アミド樹脂、ポリアミド、ポリビニルピリジン、セルロ
ース系樹脂、ウレタン樹脂、エポキシ樹脂、カゼイン、
ポリビニルアルコール、ポリビニルピロリドンなどの絶
縁性樹脂を挙げることができる。The binder can be selected from a wide range of insulating resins and organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene and polyvinylpyrene. Preferably polyvinyl butyral,
Polyarylates (condensation polymers of bisphenol A and phthalic acid, etc.), polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyridine, cellulose resin, urethane resin, epoxy resin, casein,
Examples include insulating resins such as polyvinyl alcohol and polyvinylpyrrolidone.

電荷発生層中に含有する樹脂は、８０重量％以下、好ま
しくは４０重１％以下が適している。塗工の際に用いる
有機溶剤としては、メタノール、エタノール、イソプロ
パツールなどのアルコール類、アセトン、メチルエチル
ケトン、シクロヘキサノンなどのケトン類、Ｎ、Ｎ−ジ
メチルホルムアミド。The resin contained in the charge generation layer is suitably 80% by weight or less, preferably 40% by weight or less and 1% by weight or less. Examples of organic solvents used during coating include alcohols such as methanol, ethanol and isopropanol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, and N,N-dimethylformamide.

Ｎ、Ｎ−ジメチルアセトアミドなどのアミド類、ジメチ
ルスルホキシドなどのスルホキシド類、テトラヒドロフ
ラン、ジオキサン、エチレングリコールモノメチルエー
テルなどのエーテル類、酢酸メチル、酢酸エチルなどの
エステル類、クロロホルム、塩化メチレン、ジクロルエ
チレン、四塩化炭素、トリクロルエチレンなどの脂肪族
ハロゲン化炭化水素類あるいはベンゼン、トルエン、キ
シレン、モノクロルベンゼン、ジクロルベンゼンなどの
芳香族類などを用いることができる。Amides such as N,N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide, ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate, chloroform, methylene chloride, dichloroethylene, Aliphatic halogenated hydrocarbons such as carbon tetrachloride and trichloroethylene, or aromatics such as benzene, toluene, xylene, monochlorobenzene and dichlorobenzene can be used.

塗工は、前述のコーティング法を用いて行なうことがで
きる。Coating can be performed using the coating method described above.

電荷発生層は、十分な吸光度を得るために、できる限り
多くの前記有機光導電体を含有し、且つ発生した電荷キ
ャリアの寿命内にキャリアを電荷輸送層へ注入するため
に、薄膜層、例えば５μｍ以下、好ましくは０．０１μ
ｍ〜１μｍの膜厚をもつ薄膜層とすることが好ましい。The charge generation layer contains as much of the organic photoconductor as possible in order to obtain sufficient absorbance and in order to inject carriers into the charge transport layer within the lifetime of the generated charge carriers, a thin film layer, e.g. 5 μm or less, preferably 0.01 μm
It is preferable to form a thin film layer having a thickness of m to 1 μm.

このことは、入射光量の大部分が電荷発生層で吸収され
て、多くの電荷キャリアを生成すること、さらに発生し
た電荷キャリアを再結合や捕獲（トラップ）により失活
することなく電荷輸送層に注入する必要があることに帰
因している。This means that most of the incident light is absorbed by the charge generation layer, generating many charge carriers, and that the generated charge carriers are not deactivated by recombination or trapping, but are transferred to the charge transport layer. This is due to the need for injection.

この様な電荷発生層と電荷輸送層の積層構造からなる感
光層は、導電性支持体の上に設けられる。A photosensitive layer having such a laminated structure of a charge generation layer and a charge transport layer is provided on a conductive support.

導電性支持体としては、支持体自体が導電性をもつもの
、例えばアルミニウム、アルミニウム合金、ステンレス
、ニッケル、インジウムなどを用いることができ、その
他にアルミニウム、アルミニウム合金、酸化インジウム
、酸化錫などを真空蒸着法によって被膜形成された層を
有するプラスチック（例えば、ポリエチレン、ポリプロ
ピレン、ポリ塩化ビニル、ポリエチレンテレフタレート
、アクリル樹脂、ポリフッ化エチレンなど）、導電性粒
子（例えば、アルミニウム粉末、酸化チタン、酸化錫、
酸化亜鉛、カーボンブラック、銀粒子など）を適当なバ
インダーとともにプラスチック又は前記導電性支持体の
上に被覆した支持体、導電性粒子をプラスチックや紙に
含浸した支持体や導電性ポリマーを有するプラスチック
などを用いることができる。As the conductive support, materials that have conductivity themselves, such as aluminum, aluminum alloy, stainless steel, nickel, and indium, can be used.In addition, aluminum, aluminum alloy, indium oxide, tin oxide, etc. can be used in vacuum. Plastics having a layer formed by vapor deposition (e.g., polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, polyethylene fluoride, etc.), conductive particles (e.g., aluminum powder, titanium oxide, tin oxide,
Supports such as zinc oxide, carbon black, silver particles, etc.) coated on plastic or the above-mentioned conductive support with a suitable binder, supports made of plastic or paper impregnated with conductive particles, plastics containing conductive polymers, etc. can be used.

導電性支持体と感光層の中間に、バリヤー機能と接着機
能をもつ下引層を設けることもできる。A subbing layer having barrier and adhesive functions can also be provided between the conductive support and the photosensitive layer.

下引層は、カゼイン、ポリビニルアルコール、ニトロセ
ルロース、エチレン−アクリル酸コポリマー、ポリアミ
ド、ポリウレタン、ゼラチン、酸化アルミニウムなどに
よって形成できる。The subbing layer can be formed from casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer, polyamide, polyurethane, gelatin, aluminum oxide, or the like.

下引層の膜厚は、０．１μｍ〜５μｍ、好ましくは０．
５μｍ〜３μｍが適当である。The thickness of the undercoat layer is 0.1 μm to 5 μm, preferably 0.1 μm to 5 μm.
A suitable thickness is 5 μm to 3 μm.

導電性支持体、電荷発生層、電荷輸送層の順に積層した
感光体を使用する場合において、電荷輸送物質が正孔輸
送性である場合は、電荷輸送層表面を負に帯電する必要
があり、帯電後露光すると露光部では電荷発生層におい
て生成した正孔が電荷輸送層に注入され、その後表面に
達して負電荷を中和し、表面電位の減衰が生じ未露光部
との間に静電コントラストが生じる。現像時には正電荷
性トナーを用いる必要がある。When using a photoreceptor in which a conductive support, a charge generation layer, and a charge transport layer are laminated in this order, if the charge transport material has hole transport properties, the surface of the charge transport layer must be negatively charged; When exposed to light after being charged, holes generated in the charge generation layer in the exposed area are injected into the charge transport layer, and then reach the surface and neutralize the negative charge, resulting in attenuation of the surface potential and the generation of static electricity between the exposed area and the unexposed area. Contrast occurs. During development, it is necessary to use positively charged toner.

逆に、電荷輸送物質が電子輸送性である場合は、帯電が
正、現像用トナーが負と逆に帯電させる必要がある。電
荷輸送物質が正孔輸送性であり、導電性支持体、電荷輸
送層、電荷発生層の順に積層した感光体を使用する場合
は、帯電は負、現像用トナーは正となる。On the other hand, when the charge transport material has electron transport properties, it is necessary to charge it positively and the developing toner to charge it negatively. When a photoreceptor in which the charge transport material has a hole transport property and a conductive support, a charge transport layer, and a charge generation layer are laminated in this order is used, the charge will be negative, and the developing toner will be positive.

なお、この場合、最上層の電荷発生層は主に耐刷性の問
題から、通常の電荷発生層の厚さよりかなり厚目に設定
し、かつ、キャリアの搬送性を上げるため電荷輸送物質
を加えることが多い。この場合にも本発明になる化合物
は電荷輸送物質として、または電荷輸送物質の電位特性
を安定化させる添加物として使用し得る。In this case, the topmost charge generation layer is set to be much thicker than the normal charge generation layer, mainly due to printing durability issues, and a charge transport substance is added to improve carrier transportability. There are many things. In this case as well, the compounds according to the invention can be used as charge transport substances or as additives for stabilizing the potential properties of charge transport substances.

本発明の電子写真感光体は、電子写真複写機に利用する
のみならず、レーザープリンター、ＣＲＴプリンター、
電子写真式製版システムなどの電子写真応用分野にも広
く用いることができる。The electrophotographic photoreceptor of the present invention can be used not only for electrophotographic copying machines, but also for laser printers, CRT printers,
It can also be widely used in electrophotographic application fields such as electrophotographic plate making systems.

本発明によれば、高感度で、長期にわたる繰返し帯電お
よび露光を行っても電位変動の少ない電子写真感光体を
与えることができる。According to the present invention, it is possible to provide an electrophotographic photoreceptor that is highly sensitive and exhibits little potential fluctuation even after repeated charging and exposure over a long period of time.

以下、本発明を実施例に従って説明する。Hereinafter, the present invention will be explained according to examples.

実施例１および比較例１ 下記構造式で示されるジスアゾ顔料５ｇをブチラール樹
脂（ブチラール化度７０モル％）２ｇをシクロヘキサノ
ン１００ｍ１に溶解した液とともにサンドミルで２４時
間分散し塗工液を調製した。Example 1 and Comparative Example 1 A coating solution was prepared by dispersing 5 g of a disazo pigment represented by the following structural formula together with a solution in which 2 g of butyral resin (degree of butyralization: 70 mol %) dissolved in 100 ml of cyclohexanone in a sand mill for 24 hours.

この塗工液をアルミシート上に乾燥膜厚が０．２μｍと
なる様にマイヤーバーで塗布し電荷発生層を形成した。This coating solution was applied onto an aluminum sheet using a Mayer bar to a dry film thickness of 0.2 μm to form a charge generation layer.

次に電荷輸送物質として下記構造のヒドラゾンＬｏｇと
前記例示化合物Ｎα１　１．Ｏｇとポリカーボネート樹
脂（平均分子量２００００）　１０ｇをモノクロルベン
ゼン７０ｇに溶解し、この液を先の電荷発生層の上にマ
イヤーバーで塗布し乾燥膜厚が２０μｍの電荷輸送層を
設は積層型の感光層を有する電子写真感光体を製造した
。Next, as a charge transport substance, hydrazone Log having the following structure and the above-mentioned exemplary compound Nα1 1. Dissolve Og and 10 g of polycarbonate resin (average molecular weight 20,000) in 70 g of monochlorobenzene, and apply this solution onto the charge generation layer using a Mayer bar to form a charge transport layer with a dry film thickness of 20 μm. An electrophotographic photoreceptor having layers was manufactured.

この様にして製造した電子写真感光体を川口電機（株）
製静電複写紙試験装置Ｍｏｄｅｌ−３Ｐ−４２８を用い
てスタチック方式で一５ＫＶでコロナ帯電し、暗所で１
秒間保持した後、照度２０　ｊ！　ｕｘで露光し帯電特
性を調べた。The electrophotographic photoreceptor manufactured in this way was sold to Kawaguchi Electric Co., Ltd.
Electrostatic copying paper tester Model-3P-428 was used to statically charge the corona at 15 KV, and the test was carried out in the dark at 1
After holding for a second, the illuminance is 20 j! It was exposed to UV light and its charging characteristics were examined.

帯電特性としては、表面電位（ｖｏ）と１秒間暗減衰さ
せた時の電位（ｖｌ）を％に減衰するに必要な露光量（
Ｅ　’Ａ　）を測定した。The charging characteristics include the surface potential (vo) and the amount of light exposure required to attenuate the potential (vl) when dark decaying for 1 second to % (
E'A) was measured.

さらに、繰り返し使用した時の明部電位と暗部電位の変
動を測定するために、本実施例で作成した感光体のキャ
ノン（株）製ＰＰＣ複写機ＮＰ−３５２５の感光ドラム
用シリンダーに貼り付けて、同機で５００００枚複写を
行い、初期と５００００枚複写後の明部電位（Ｖｔ、）
及び暗部電位（ＶＤ）の変動を測定した。Furthermore, in order to measure the fluctuations in bright area potential and dark area potential during repeated use, the photoreceptor prepared in this example was attached to the photosensitive drum cylinder of a PPC copier NP-3525 manufactured by Canon Inc. , 50,000 copies were made with the same machine, and the bright area potential (Vt, ) at the initial stage and after 50,000 copies was made.
and changes in dark potential (VD) were measured.

尚、初期のＶＤとｖＬは各＃−７００Ｖ、−２００Ｖと
なる様に設定した。また比較の為に例示化合物Ｎαｌを
含まない電荷輸送物質のみの感光体を製造し、同様に測
定を行った。Incidentally, the initial VD and vL were set to be -700V and -200V, respectively. In addition, for comparison, a photoreceptor containing only a charge transport material without containing the exemplified compound Nαl was manufactured, and measurements were conducted in the same manner.

この結果を第１表に示す。The results are shown in Table 1.

第　　　１　　　表 第１表より、明らかに本発明の化合物を用いた場合は良
好な感度を維持し耐久時の電位変動も少ないことが判る
。また、初期と同じ条件で５００００枚後の画出しを行
ったところ、実施例にほとんど変化なかったが、比較例
は地力ブリの多い画像となった。Table 1 From Table 1, it is clear that when the compounds of the present invention are used, good sensitivity is maintained and potential fluctuations during durability are small. Further, when images were printed after 50,000 sheets under the same conditions as the initial condition, there was almost no change in the images in the examples, but the images in the comparative examples had a lot of blurring.

実施例２〜１３および比較例２〜７ この各実施例においては、前記実施例１で用いた電荷輸
送物質の代りに下記構造の７員環を有する化合物を用い
、 更に例示化合物（１）の代りに例示化合物Ｎα（３）（
２３）　（２６）を各々添加し、かつ電荷発生物質とし
て下記構造の顔料を用いたほかは、実施例１と同様の方
法によって電子写真感光体を製造した。Examples 2 to 13 and Comparative Examples 2 to 7 In each of these Examples, a compound having a 7-membered ring having the following structure was used in place of the charge transport substance used in Example 1, and further, exemplified compound (1) was used. Instead, exemplified compound Nα(3)(
23) An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that each of (26) was added and a pigment having the structure shown below was used as a charge generating substance.

各感光体の電子写真特性を耐久特性を１００００枚とし
た他は実施例１と同様の方法によって測定した。The electrophotographic characteristics of each photoreceptor were measured in the same manner as in Example 1, except that the durability characteristics were changed to 10,000 sheets.

その結果を次の第２表に示す。また比較例として本発明
の化合物を添加しない場合、更には本発明以外の各種の
化合物を添加した場合の感光体についても同様な測定を
行い第３表に記した。The results are shown in Table 2 below. Further, as a comparative example, similar measurements were performed on photoreceptors in which the compound of the present invention was not added, and furthermore, various compounds other than the present invention were added, and the results are shown in Table 3.

第２表および第３表から明らかなように本発明になる化
合物を用いた場合は従来のものに比べて良好な感度を維
持し、耐久時の電位変動も少ない。As is clear from Tables 2 and 3, when the compounds of the present invention are used, better sensitivity is maintained compared to conventional ones, and potential fluctuations during durability are also small.

また、前記の複写機ＮＰ−３５２５を用いて画出し試験
を行った後、翌朝までそのまま放置して、黒紙を複写し
たところ、本発明になる化合物を感光層中に含有させた
実施例は全て良好な黒色画像を得たのに対し、比較例は
強度の差はあるものの例外なく帯電器に面した部分が白
く抜けるといういわゆる白抜は現象を生じた。これから
、本発明になる化合物は、複写機内、特に帯電器で形成
されるオゾン、ＮＯｘ、硝酸等に対してきわめて有効で
あることが判る。Further, after conducting an image reproduction test using the above-mentioned copying machine NP-3525, the black paper was copied by leaving it as it was until the next morning. In all cases, good black images were obtained, whereas in the comparative examples, although there were differences in intensity, the so-called white spot phenomenon occurred in which the portion facing the charger appeared white without exception. From this, it can be seen that the compound of the present invention is extremely effective against ozone, NOx, nitric acid, etc. formed in a copying machine, particularly in a charger.

実施例１４〜２４及び比較例８ 電荷発生物質として下記の構造の顔料を用い、電荷輸送
物質としては、例示化合物Ｎα（２５）　（２６）（４
１）を用いて、添加剤を加えることな（、実施例１と同
様にして電子写真感光体を製造した。Examples 14 to 24 and Comparative Example 8 Pigments with the following structures were used as charge-generating substances, and exemplary compounds Nα(25) (26)(4) were used as charge-transporting substances.
1), an electrophotographic photoreceptor was produced in the same manner as in Example 1 without adding any additives.

また比較例として、下記構造の化合物を電荷輸送化合物
として用い同様にして電子写真感光体を製造した。As a comparative example, an electrophotographic photoreceptor was produced in the same manner using a compound having the structure shown below as a charge transporting compound.

各感光体の電子写真特性を実施例１と同様の方法によっ
て測定した。その結果を第４表に示す。The electrophotographic properties of each photoreceptor were measured in the same manner as in Example 1. The results are shown in Table 4.

本発明になる化合物は電位の安定性に寄与することはむ
ろん、感度においても優れた特性を示している。一方比
較例はアリールチオ基が一つの為か電位の安定性に対す
る寄与は十分でない。The compound of the present invention not only contributes to potential stability but also exhibits excellent characteristics in terms of sensitivity. On the other hand, in the comparative example, the contribution to potential stability is not sufficient, probably because there is only one arylthio group.

実施例２５ アルミニウムシリンダー上にカゼインのアンモニア水溶
液（カゼイン１１．２ｇ、　２８％アンモニア水１ｇ１
水２２２ｍＡ）をブレードコーティング法で塗布し乾燥
膜厚１μｍの下引層を形成した。Example 25 Aqueous ammonia solution of casein (11.2 g of casein, 1 g of 28% aqueous ammonia)
Water (222 mA) was applied using a blade coating method to form a subbing layer with a dry film thickness of 1 μm.

次に下記構造式で示される電荷発生物質１０ｇ。Next, 10 g of a charge generating substance represented by the following structural formula.

ブチラール樹脂（ブチラール化度６３モル％）５ｇとシ
クロへキサノン２００ｇを、ボールミル分散機で４８時
間分散を行った。この分散液を先に製造した下引層の上
にブレードコーティング法により塗布し、乾燥膜厚０．
１５μｍの電荷発生層を形成した。5 g of butyral resin (butyralization degree: 63 mol%) and 200 g of cyclohexanone were dispersed for 48 hours using a ball mill disperser. This dispersion was applied onto the previously prepared undercoat layer using a blade coating method, and the dry film thickness was 0.
A charge generation layer of 15 μm was formed.

次に前記例示化合物Ｎｏ、（３６）　１０ｇ、ポリメチ
ルメタクリレート樹脂（平均分子量５０，０００）１０
ｇをモノクロルベンゼン７０ｇに溶解し、先に形成した
電荷発生層の上にブレードコーティング法により塗布し
、乾燥膜厚１９μｍの電荷輸送層を形成した。Next, 10 g of the exemplified compound No. (36), 10 g of polymethyl methacrylate resin (average molecular weight 50,000)
g was dissolved in 70 g of monochlorobenzene and coated on the previously formed charge generation layer by a blade coating method to form a charge transport layer with a dry film thickness of 19 μm.

こうして製造した感光体に一５ＫＶのコロナ放電を行な
った。この時の表面電位を測定した（初期電位Ｖ。）。A corona discharge of 15 KV was applied to the photoreceptor thus produced. The surface potential at this time was measured (initial potential V).

さらに、この感光体を１秒間暗所で放置した後の表面電
位を測定した。感度は、暗減衰した後の電位ｖ１を％に
減衰するに必要な露光量（８％、マイクロジュール／　
ｃ　ｒｄ　）を測定することによって評価した。この際
、光源としてガリウム／アルミニウム／上素の三元系半
導体レーサー（出カニ５ｍｗ；発振波長７８０　ｎ　ｍ
　）を用いた。これらの結果は、次のとおりであった。Furthermore, the surface potential of this photoreceptor was measured after it was left in a dark place for 1 second. The sensitivity is the exposure amount (8%, microjoules/
The evaluation was made by measuring the c rd ). At this time, as a light source, a ternary semiconductor laser of gallium/aluminum/superoxide (output 5 mw; oscillation wavelength 780 nm) was used.
) was used. These results were as follows.

Ｖｏ　：　　−６８０Ｖ Ｖ、　　：　　−６６５Ｖ ＥＨ：　　　１．１？イクロジユ一ル／ｃｍ”次に同上
の半導体レーザーを備えた反転現像方式の電子写真方式
プリンターであるレーザービームプリンター（キャノン
製ＬＢＰ−ＣＸ）に上記感光体をＬＢＰ−ＣＸの感光体
に置き換えてセットし、実際の画像形成テストを用いた
。条件は以下の通りである。−次帯電後の表面電位ニー
７００Ｖ、像露光後の表面電位；　−１５０Ｖ　（露光
量２．０μＪ　／　ｃｄ）転写電位＋７００Ｖ、現像剤
極性；負極性、プロセススピード；５０ｍｍ／ｓｅｃ、
現像条件（現像バイアス）；−４５０Ｖ、像露光スキャ
ン方式；イメージスキャン、−次帯電前露光；　５０　
ｊ！　ｕｘ　拳ｓｅｃの赤色全面露光、画像形成はレー
ザービームを文字信号及び画像信号に従ってラインスキ
ャンして行　なつたが、文字、画像共に良好なプリント
が得られた。更に、連続３０，０００枚の画出しを行っ
たところ初期から３０，０００枚まで安定した良好なプ
リントが得られた。Vo: -680V V,: -665V EH: 1.1? Next, replace the above photoconductor with an LBP-CX photoconductor and set it in a laser beam printer (Canon LBP-CX), which is a reversal development type electrophotographic printer equipped with the same semiconductor laser. An actual image forming test was used.The conditions were as follows: - Surface potential after secondary charging: knee 700V, surface potential after image exposure: -150V (exposure amount: 2.0 μJ/cd) Transfer potential: +700V , developer polarity: negative polarity, process speed: 50 mm/sec,
Development conditions (development bias): -450V, image exposure scan method: image scan, -exposure before next charging; 50
j! The whole surface was exposed to red light for 10 seconds, and the image was formed by line scanning a laser beam in accordance with the character and image signals, and good prints were obtained for both the characters and the image. Furthermore, when 30,000 images were printed continuously, stable and good prints were obtained from the initial stage up to 30,000 sheets.

実施例２６ ４−（４−ジメチルアミノフェニル）−２，６−シフエ
ニルチアピリリウムパークロレート３ｇとポリ（４，４
’−イソプロピリデンジフェニレンカーボネート）３ｇ
をジクロルメタン２００　ｍ　ｌに十分に溶解した後、
トルエン１００ｍｊ！を加え、共晶錯体を沈澱させた。Example 26 3 g of 4-(4-dimethylaminophenyl)-2,6-cyphenylthiapyrylium perchlorate and poly(4,4
'-isopropylidene diphenylene carbonate) 3g
After sufficiently dissolving in 200 ml of dichloromethane,
Toluene 100mj! was added to precipitate the eutectic complex.

この沈澱物をろ別した後、ジクロルメタンを加えて再溶
解し、次いでこの溶液にｎ−ヘキサン１００　ｔｎ　１
を加えて共晶錯体の沈澱物を得た。After filtering this precipitate, dichloromethane was added to dissolve it again, and then 100 tn 1 of n-hexane was added to this solution.
was added to obtain a precipitate of a eutectic complex.

この共晶錯体５ｇをポリビニルブチラール２ｇを含有す
るメタノール溶液９５ｍＪに加え、６時間ボールミルで
分散した。この分散液をカゼイン層を有するアルミ板の
上に乾燥後の膜厚が０．４μｍとなる様にマイヤーバー
で塗布して電荷発生層を形成した。5 g of this eutectic complex was added to 95 mJ of a methanol solution containing 2 g of polyvinyl butyral, and dispersed in a ball mill for 6 hours. This dispersion was applied onto an aluminum plate having a casein layer using a Mayer bar so that the film thickness after drying was 0.4 μm to form a charge generation layer.

次いで、この電荷発生層の上に例示化合物（２９）を用
いる以外は実施例１と全く同様にして電荷輸送層の被覆
層を形成した。Next, a cover layer of a charge transport layer was formed on this charge generation layer in exactly the same manner as in Example 1 except that exemplified compound (29) was used.

こうして製造した感光体の電子写真特性を実施例１と同
様の方法によって測定した。この結果を次に示す。The electrophotographic properties of the photoreceptor thus produced were measured in the same manner as in Example 1. The results are shown below.

Ｖｏ：６９０Ｖ Ｖ、　　：　　−６７５Ｖ Ｅ　％　　：　　１．３　ｊ！ｕｘ＠ｓｅｃ初−御所 ＶＤ　　　：　　　−７００Ｖ ＶＬ　　　：　　　−２００Ｖ １００００ｏ　　　　　’。Vo:690V V: -675V E%: 1.3j! ux@sec first-gosho VD: -700V VL: -200V 10000o.'

ＶＤ　　　：　　　−６７５Ｖ ＶＬ　　　：　　　−２３０Ｖ 〔発明の効果〕 以上説明したように本発明になる化合物を含有する電子
写真感光体は高感度であり、また特に長期にわたる繰返
し帯電、露光による連続画像形成に際して明部電位と暗
部電位の変動が小さいため、耐久性に優れた特性の感光
体を与えるものである。VD: -675V VL: -230V [Effects of the Invention] As explained above, the electrophotographic photoreceptor containing the compound of the present invention has high sensitivity and is particularly stable during continuous image formation by repeated charging and exposure over a long period of time. Since fluctuations in the partial potential and dark potential are small, a photoreceptor with excellent durability can be obtained.

また本発明になる化合物は、オゾン、ＮＯｘ、硝酸等に
よる白抜は現象に対しても極めて有効なものである。Furthermore, the compound of the present invention is extremely effective against white removal phenomena caused by ozone, NOx, nitric acid, and the like.

Claims (3)

【特許請求の範囲】[Claims] （１）導電性支持体上に感光層を有する電子写真感光体
において、構造式中に、 一般式（ I ） ▲数式、化学式、表等があります▼………（ I ） で示されるジ置換アミノアリール基と、 一般式（II） −Ｓ−Ｒ＿３………（II） で示される鎖状スルフィド構造と、 一般式（III） −Ｓ−Ｒ＿４………（III） で示される鎖状スルフィド構造とを併せ持った化合物を
感光層中に含有することを特徴とする電子写真感光体。 ［式中、Ｒ＿１およびＲ＿２は、置換基を有してもよい
アルキル基、アリール基、アラルキル基またはＲ＿１と
Ｒ＿２で結合して５ないし６員環を形成するのに必要な
残基を示し、Ａｒは置換基を有してもよいアリーレン基
を示し、Ｒ＿３は置換基を有してもよいアリール基を示
し、Ｒ＿４は置換基を有してもよいアルキル基、アリー
ル基、またはアラルキル基を示す。］(1) In an electrophotographic photoreceptor having a photosensitive layer on a conductive support, the structural formula includes general formula (I) ▲Mathematical formula, chemical formula, table, etc.▼……(I) Disubstitution An aminoaryl group, a chain sulfide structure represented by the general formula (II) -S-R_3 (II), and a chain sulfide structure represented by the general formula (III) -S-R_4 (III) 1. An electrophotographic photoreceptor characterized by containing a compound having a structure in a photosensitive layer. [In the formula, R_1 and R_2 represent an alkyl group, an aryl group, an aralkyl group, which may have a substituent, or a residue necessary to combine R_1 and R_2 to form a 5- to 6-membered ring, Ar represents an arylene group that may have a substituent, R_3 represents an aryl group that may have a substituent, and R_4 represents an alkyl group, an aryl group, or an aralkyl group that may have a substituent. show. ] （２）前記化合物が感光層に含有される電荷輸送物質と
して用いられる特許請求の範囲第１項記載の電子写真感
光体。(2) The electrophotographic photoreceptor according to claim 1, wherein the compound is used as a charge transport material contained in the photosensitive layer. （３）前記化合物が、感光層に含有される電荷輸送物質
に対する添加物として用いられる特許請求の範囲第１項
記載の電子写真感光体。(3) The electrophotographic photoreceptor according to claim 1, wherein the compound is used as an additive to a charge transport substance contained in the photosensitive layer.
JP29644787A 1987-11-24 1987-11-24 Electrophotographic sensitive body Granted JPH01136161A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP29644787A JPH01136161A (en) 1987-11-24 1987-11-24 Electrophotographic sensitive body
US07/274,503 US4931371A (en) 1987-11-24 1988-11-21 Electrophotographic photosensitive member
FR8815260A FR2623638B1 (en) 1987-11-24 1988-11-23 IMPROVED PHOTOSENSITIVE ELECTROPHOTOGRAPHIC SUPPORT

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP29644787A JPH01136161A (en) 1987-11-24 1987-11-24 Electrophotographic sensitive body

Publications (2)

Publication Number Publication Date
JPH01136161A true JPH01136161A (en) 1989-05-29
JPH0549227B2 JPH0549227B2 (en) 1993-07-23

Family

ID=17833661

Family Applications (1)

Application Number Title Priority Date Filing Date
JP29644787A Granted JPH01136161A (en) 1987-11-24 1987-11-24 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPH01136161A (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5117442A (en) * 1974-08-03 1976-02-12 Mitsubishi Paper Mills Ltd JUKIKO HANDOTAIDENS HISHASHINZAIRYO
JPS524242A (en) * 1975-06-28 1977-01-13 Ricoh Co Ltd Electronic photo sensitive agent
JPS6198353A (en) * 1984-10-19 1986-05-16 ゼロツクス　コーポレーシヨン Photosensor containing aromatic eter hole transfer layer
JPS61228450A (en) * 1985-04-03 1986-10-11 Ricoh Co Ltd Electrophotographic sensitive body
JPS61229849A (en) * 1985-04-03 1986-10-14 Ricoh Co Ltd Aromatic amino derivative and production thereof
JPS62134652A (en) * 1985-12-06 1987-06-17 Ricoh Co Ltd Electrophotographic sensitive body

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5117442A (en) * 1974-08-03 1976-02-12 Mitsubishi Paper Mills Ltd JUKIKO HANDOTAIDENS HISHASHINZAIRYO
JPS524242A (en) * 1975-06-28 1977-01-13 Ricoh Co Ltd Electronic photo sensitive agent
JPS6198353A (en) * 1984-10-19 1986-05-16 ゼロツクス　コーポレーシヨン Photosensor containing aromatic eter hole transfer layer
JPS61228450A (en) * 1985-04-03 1986-10-11 Ricoh Co Ltd Electrophotographic sensitive body
JPS61229849A (en) * 1985-04-03 1986-10-14 Ricoh Co Ltd Aromatic amino derivative and production thereof
JPS62134652A (en) * 1985-12-06 1987-06-17 Ricoh Co Ltd Electrophotographic sensitive body

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