JPH01105955A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPH01105955A
JPH01105955A JP26320987A JP26320987A JPH01105955A JP H01105955 A JPH01105955 A JP H01105955A JP 26320987 A JP26320987 A JP 26320987A JP 26320987 A JP26320987 A JP 26320987A JP H01105955 A JPH01105955 A JP H01105955A
Authority
JP
Japan
Prior art keywords
substituted
carrier
layer
unsubstituted
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP26320987A
Other languages
Japanese (ja)
Inventor
Eiichi Sakai
坂井　栄一
Yoshiaki Takei
武居　良明
Naoto Abe
直人 安部
Osamu Sasaki
佐々木　収
Satoshi Goto
聰 後藤
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.)
Konica Minolta Inc
Original Assignee
Konica Minolta 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 Konica Minolta Inc filed Critical Konica Minolta Inc
Priority to JP26320987A priority Critical patent/JPH01105955A/en
Publication of JPH01105955A publication Critical patent/JPH01105955A/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • 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
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
    • 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
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups
    • 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
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups
    • G03G5/0674—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups containing hetero rings

Abstract

PURPOSE:To form an electrophotographic sensitive body having high durability to light, ozone, etc. by providing a photosensitive layer contg. a compd. expressed by a specified compositional formula contg. a substituted or unsubstituted arylene group, aryl group, or aromatic substituted alkyl group, etc., on an electroconductive base. CONSTITUTION:A photosensitive layer contg. at least one compd. expressed by the formula I and at least one compd. expressed by the formula II is formed on an electroconductive base. In the formulas, each Ar1, Ar2, Ar3 and Ar9 is substituted or unsubstituted arylene group; each Ar4, Ar5, Ar6, Ar7, Ar8 and Ar10 is an substituted or unsubstituted aryl group, aromatic substituted or unsubstituted alkyl group, or substituted or unsubstituted heterocyclic group; each R1, R2, R3 and R5 is H, substituted or unsubstituted alkyl group, or substituted or unsubstituted aryl group. This electrophotographic sensitive body utilizing a carrier transfer material has high durability to light, ozone and electric charge, having also superior stability of charged potential, residual potential and sensitivity even if it is used for a long time.

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、より詳しくは、有機光
導電性化合物を主成分とする感光層を有する新規な電子
写真感光体に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to a novel electrophotographic photoreceptor having a photosensitive layer containing an organic photoconductive compound as a main component.

〔従来技術〕[Prior art]

従来電子写真感光体としては、セレン、酸化亜鉛、硫化
カドミウム、シリコン等の無機光導電性化合物を主成分
とする感光層を有する無機感光体が広く用いられてきた
。しかしこれらは、感度、熱安定性、耐湿性、耐久性等
において必ずしも満足し得るものではなかった。たとえ
ばセレンは、結晶化すると電子写真感光体としての特性
が劣化してしまうため製造上も難しく、また熱や指紋等
が原因となり結晶化し、電子写真感光体としての性能が
劣化してしまう。また硫化カドミウムや酸化亜鉛では、
耐湿性や耐久性に問題があった。Conventionally, inorganic photoreceptors having a photosensitive layer containing an inorganic photoconductive compound such as selenium, zinc oxide, cadmium sulfide, or silicon as a main component have been widely used as electrophotographic photoreceptors. However, these were not necessarily satisfactory in terms of sensitivity, thermal stability, moisture resistance, durability, etc. For example, when selenium crystallizes, its properties as an electrophotographic photoreceptor deteriorate, making it difficult to manufacture.Also, selenium crystallizes due to heat, fingerprints, etc., and its performance as an electrophotographic photoreceptor deteriorates. In addition, cadmium sulfide and zinc oxide
There were problems with moisture resistance and durability.

これら無機感光体の持つ欠点を克服する目的で、様々な
有機光導電性化合物を主成分とする感光層を有する有機
感光体の研究開発が近年盛んに行なわれている。In order to overcome these drawbacks of inorganic photoreceptors, research and development have been actively conducted in recent years on organic photoreceptors having photosensitive layers containing various organic photoconductive compounds as main components.

たとえば、特公昭５０−１０４９６号にはポリ−Ｎ−ビ
ニルカルバゾールと２．４．７−ドリニトロー９−フル
オレノンを含有する感光層で構成した有機感光体の記載
がある。しかしこの感光体は、感度および耐久性におい
て、必ずしも満足できるものではない。For example, Japanese Patent Publication No. 50-10496 describes an organic photoreceptor comprising a photosensitive layer containing poly-N-vinylcarbazole and 2,4,7-dolinitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in terms of sensitivity and durability.

この様な欠点を改良するために、キャリア発生機能とキ
ャリア輸送機能とを異なる物質に分担させ高性能の有機
感光体を開発する試みがなされている。この様ないわゆ
る機能分離型の感光体は、各々の材料を広い範囲から選
択することができ、任意の性能を有する感光体を比較的
容易に作成し得ることから多くの研究がなされてきた。In order to improve these drawbacks, attempts have been made to develop a high-performance organic photoreceptor in which the carrier generation function and the carrier transport function are shared by different substances. Many studies have been conducted on such so-called functionally separated photoreceptors because each material can be selected from a wide range and a photoreceptor having arbitrary performance can be produced relatively easily.

その結果キャリア発生物質としては、各種のアゾ化合物
が開発され実用に供されている。As a result, various azo compounds have been developed and put into practical use as carrier-generating substances.

一方、キャリア輸送物質についても、たとえば特開昭５
１−９４８２９号、同５２−７２２３１号、同５３−２
７０３３号、同５５−５２０６３号、同５８−６５４４
０号、同５８−１９８４２５号等に開示されている如く
、ヒドラゾン系化合物、スチリルフェニルアミン化合物
等多岐にわたる物質が提案されている。しかしながら、
これらの物質をキャリア輸送物質とした場合に繰返し使
用に際して感度の低下があり、かつ帯電電位の変動、残
留電位の上昇などの問題点があった。On the other hand, regarding carrier transport substances, for example,
No. 1-94829, No. 52-72231, No. 53-2
No. 7033, No. 55-52063, No. 58-6544
As disclosed in No. 0, No. 58-198425, etc., a wide variety of substances have been proposed, such as hydrazone compounds and styryl phenylamine compounds. however,
When these materials are used as carrier transport materials, there are problems such as a decrease in sensitivity upon repeated use, fluctuations in charging potential, and increases in residual potential.

このような欠点を改良するため、特開昭６０−１７５０
５２号、同６２−１２０３４６号ではジスチリルトリフ
ェニルアミン系化合物をキャリア輸送物質として使用す
ることが提案されている。しかしながらこのような化合
物を単独で用いた場合には繰返し使用時の感度低下、帯
電電位の変動、残留電位の上昇などの問題点が充分解決
されずに残されており、しかもこの場合キャリア輸送物
質の溶媒への溶解性が不十分になることがあり、製造上
問題を有することがあった。In order to improve these drawbacks, Japanese Patent Application Laid-Open No. 60-1750
No. 52 and No. 62-120346 propose the use of distyryltriphenylamine compounds as carrier transport materials. However, when such compounds are used alone, problems such as decreased sensitivity during repeated use, fluctuations in charging potential, and increased residual potential remain unsolved. The solubility in the solvent may be insufficient, which may cause manufacturing problems.

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

前記のごときキャリア輸送物質を使用した電子写真感光
体には、比較的優れた電子写真性能を示すものもあるが
、光、オゾンあるいは電気的負荷に対する耐久性が弱く
、繰返し使用時において性能が不安定で劣化等を生じる
ため実用上の要求を十分満足させるものではなく、更に
すぐれたキャリア輸送機能を有し、かつ長期間の使用に
対して帯電電位、残置電位及び感度の安定性のよい、ま
た溶解性の充分なキャリア輸送物質の開発が望まれる。Some electrophotographic photoreceptors using carrier transport materials such as those described above exhibit relatively excellent electrophotographic performance, but their durability against light, ozone, or electrical loads is weak, and performance may deteriorate after repeated use. It does not fully satisfy practical requirements because it is stable and causes deterioration, but it also has an excellent carrier transport function and has good stability in charging potential, residual potential, and sensitivity for long-term use. It is also desired to develop a carrier transporting substance with sufficient solubility.

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

前記の問題は、導電性支持体上に下記一般式（Ｉ）及び
［１１）で示されるキャリア輸送物質を含有する層を含
んで構成される感光層を有する電子写真感光体によって
解決された。The above problem has been solved by an electrophotographic photoreceptor having a photosensitive layer comprising a conductive support and a layer containing a carrier transporting substance represented by the following general formulas (I) and [11].

一般式〔工〕 一般式〔■） 式中、Ａ　ｒｌ、Ａ　ｒ２．Ａ　ｒｌ及びＡｒ、は置換
、未置換のアリーレン基、好ましくは置換、未置換のフ
ェニレン基、置換、未置換のす７チレン基を表し、Ａ　
ｒ　４　＋　Ａ　ｒ　ｓ　＋　Ａ　ｒ　ａ　、　Ａ　ｒ
　７　、　Ａ　ｒ　ｓ及びＡ　ｒ　Ｉ　Ｏは置換、未置
換のアリール基、芳香族置換アルキル基及び置換、未置
換の複素環基を表し、好ましくは置換。General formula [English] General formula [■] In the formula, A rl, A r2. A rl and Ar represent a substituted or unsubstituted arylene group, preferably a substituted or unsubstituted phenylene group, or a substituted or unsubstituted styrene group;
r 4 + A r s + A r a , A r
7, A r s and A r I O represent a substituted or unsubstituted aryl group, an aromatic substituted alkyl group, and a substituted or unsubstituted heterocyclic group, preferably substituted.

未置換のナフチル基を表し、Ｒｌ＋Ｒ２，Ｒ３，Ｒ４及
びＲ５は、水素原子、置換、未置換のアルキル基、置換
、未置換のアリール基を表し、好ましくは水素原子、炭
素原子数１個から８個のアルキル基、置換、未置換のフ
ェニル基、置換、未置換のす７チル基を表す。Represents an unsubstituted naphthyl group, and Rl+R2, R3, R4 and R5 represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, preferably a hydrogen atom or a carbon atom having 1 to 8 carbon atoms. represents an alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted s7tyl group.

すなわち本発明においては、前記一般式〔Ｔ〕。That is, in the present invention, the general formula [T].

（ｎ）で示される化合物の阜ヤリア輸送能を活用し、こ
れをキャリアの発生と輸送とをそれぞれ別個の物質で行
ういわゆる機能分離型電子写真感光体のキャリア輸送物
質として用いることにより、被膜物性に優れ、電荷保持
力、感度、残留電位等の電子写真特性に優れ、かつ繰返
し使用に供したときにも疲労劣化が少ない上、熱、オゾ
ンあるいは光に対しても安定した特性を発揮し得る電子
写真感光体を作成することができる。By utilizing the carrier transport ability of the compound shown in (n) and using it as a carrier transport material for a so-called functionally separated electrophotographic photoreceptor in which carrier generation and transport are performed using separate substances, the physical properties of the film can be improved. It has excellent electrophotographic properties such as charge retention, sensitivity, and residual potential, and exhibits little fatigue deterioration even after repeated use, and exhibits stable properties against heat, ozone, and light. An electrophotographic photoreceptor can be created.

また本発明で用いられるキャリア輸送物質は、前記一般
式（Ｉ）、（ｎ）で示される夫々の化合物の中から夫々
少くとも１種の組合せで併用される。Further, the carrier transport substance used in the present invention is used in combination with at least one type of the compounds represented by the above general formulas (I) and (n).

また他のキャリア輸送物質を加え組合せて使用しても良
い。Further, other carrier transport substances may be added and used in combination.

前記併用する量比［：Ｉ）／ＩＩ［）は３／９７〜９７
／３、好ましくは５／９５〜５０／　５０である。The above-mentioned combined use ratio [:I)/II[) is 3/97 to 97
/3, preferably 5/95 to 50/50.

前記一般式〔Ｉ〕で示される本発明に有効なキャリア輸
送物質の具体例としては、例えば、次の構造式を有する
ものが挙げられるが、これによって本発明に係るキャリ
ア輸送物質が限定されるものではない。Specific examples of the carrier transport substance represented by the general formula [I] that are effective in the present invention include those having the following structural formula, but the carrier transport substance according to the present invention is limited by this. It's not a thing.

例示化合物 （５ン （Ｉ３） ＱＣ）ｌ、　　ＯＣＲ３ 前記キャリア輸送物質は、公知の方法によって容易に合
成される。たとえば特開昭５８−６５４４０号および特
開昭５８−１９８４２５号記載の方法が参照される。Exemplary Compound (I3) QC, OCR3 The carrier transport substance is easily synthesized by a known method. For example, reference may be made to the methods described in JP-A-58-65440 and JP-A-58-198425.

次に一般式（Ｉ［）で示されるキャリア輸送物質の具体
例としては、下記の構造式を有するスチル化合物が挙げ
られるが、これらに限定されるものではない。Next, specific examples of the carrier transport substance represented by the general formula (I[) include still compounds having the following structural formula, but are not limited thereto.

以下余白 前記一般式〔ＩＩ〕で示されるスチル化合物は特開昭５
８−５８５５０号、同５８−６５４４０号、同５８−１
９８０４３号等の公知の合成法により調製することがで
きる。The still compound represented by the above general formula [II] in the margin below is JP-A No. 5
No. 8-58550, No. 58-65440, No. 58-1
It can be prepared by a known synthesis method such as No. 98043.

次に本発明に適するキャリア発生物質としては、アゾ顔
料が好ましいが、一般には可視光から赤外光を吸収して
、フリーキャリアを発生するものであれば無機顔料およ
び有機顔料のいずれをも用いることができる。Next, as a carrier generating substance suitable for the present invention, an azo pigment is preferable, but in general, any inorganic pigment or organic pigment can be used as long as it absorbs visible light to infrared light and generates free carriers. be able to.

例えば無定形セレン、三方晶形セレン、セレン砒素合金
、セレン−テルル合金、硫化カドミウム等の無機顔料の
ほか、次の代表例で示されるような有機顔料を用いても
良い。For example, in addition to inorganic pigments such as amorphous selenium, trigonal selenium, selenium arsenic alloy, selenium-tellurium alloy, and cadmium sulfide, organic pigments such as those shown in the following representative examples may be used.

（１）　　モノアゾ顔料、ビスアゾ顔料、トリスアゾ顔
料、金属錯塩アゾ顔料等のアゾ顔料 （２）ペリレン酸無水物、ペリレン酸イミド等のペリレ
ン系顔料 （３）　　アントラキノン誘導体、アンスアンスロン誘
導体、ジベンズピレンキノン誘導体、ピラントロン誘導
体、ビオラントロン誘導体およびイソビオラントロン誘
導体等多環キノン系顔料 （４）インジゴ誘導体およびチオインジゴ誘導体等のイ
ンジゴイド系顔料 （５）金属フタロシアニン及び無金属フタロシアニン等
のフタロシアニン系顔料 （６）　　ジフェニルメタン顔料、トリフェニルメタン
顔料、キサンチン顔料およびアクリジン顔料等のカルボ
ニウム系顔料 （７）アジン顔料、オキサジン顔料およびチアジン顔料
等のキノンイミン系顔料 （８）　シアニン顔料およびアゾメチン顔料等のメチン
系顔料 （９）　キノリン系顔料 （１０）ベンゾキノンおよびナフトキノン系顔料（１１
）　　ナフタルイミド系顔料 （１２）　　ビスベンゾイミダゾール誘導体等のペリノ
ン系顔料 本発明において用いられるキャリア輸送物質は、それ自
体では被膜形成能がないため種々の結着剤と組合せて感
光層が形成される。(1) Azo pigments such as monoazo pigments, bisazo pigments, trisazo pigments, metal complex azo pigments, etc. (2) Perylene pigments such as perylene acid anhydride, perylene acid imide, etc. (3) Anthraquinone derivatives, anthanthrone derivatives, dibenzpyrenequinone Polycyclic quinone pigments such as derivatives, pyranthrone derivatives, violanthrone derivatives and isoviolanthrone derivatives (4) Indigoid pigments such as indigo derivatives and thioindigo derivatives (5) Phthalocyanine pigments such as metal phthalocyanine and metal-free phthalocyanine (6) Diphenylmethane pigments, carbonium pigments such as triphenylmethane pigments, xanthine pigments and acridine pigments (7) quinone imine pigments such as azine pigments, oxazine pigments and thiazine pigments (8) methine pigments such as cyanine pigments and azomethine pigments (9) quinoline Benzoquinone-based pigments (10) and naphthoquinone-based pigments (11)
) Naphthalimide pigment (12) Perinone pigment such as bisbenzimidazole derivative The carrier transport substance used in the present invention does not have the ability to form a film by itself, so a photosensitive layer is formed by combining it with various binders. .

キャリア発生層およびキャリア輸送層に用いられる結着
剤としては、任意のものを用いることができるが、疎水
性の電気絶縁性フィルム形成性高分子重合体を用いるこ
とが好ましい。このような高分子重合体としては、例え
ば次のものを挙げることができるが、これらに限定され
るものではない。Although any binder can be used for the carrier generation layer and the carrier transport layer, it is preferable to use a hydrophobic electrically insulating film-forming polymer. Examples of such high molecular weight polymers include, but are not limited to, the following.

（１）ポリカーボネートが特に好ましく、例えばポリカ
ーボネートＡ及び特開昭６０−１７２０４５号に記載さ
れたカーボネートが挙げられる。(1) Polycarbonates are particularly preferred, such as polycarbonate A and the carbonates described in JP-A-60-172045.

また更に次のものを続いて挙げることができる。しかし
これらに限定されるねのではない。Furthermore, the following may be mentioned in succession: However, it is not limited to these.

（２）ポリエステル （３）メタクリル樹脂 （４）アクリル樹脂 （５）ポリ塩化ビニル （６）　ポリ塩化ビニリデン （７）ポリスチレン （８）ポリビニルアセテート （９）スチレン共重合樹脂（たとえば、スチレン−ブタ
ヂエン共重合体、スチレン−メタクリル酸メチル共重合
体、等） （１０）アクリロニトリル系共重合体樹脂（たとえば、
塩化ビニリデン−アクリトロニトリル共重合体、等） （１１）　　塩化ビニル−酢酸ビニル共重合体（１２）
塩化ビニル−酢酸ビニル−無水マレイン酸共重合体 （１３）シリコン樹脂 （１４）　　シリコン−アルキッド樹脂（１５）　　フ
ェノール樹脂（たとえば、フェノール−ホルムアルデヒ
ド樹脂、クレゾールホルムアルデヒド樹脂、等） （１６）　　スチレン−アルキッド樹脂（１７）ポリ−
Ｎ−ビニルカルバゾール（１８）ポリビニルブチラール （１９）ポリビニルホルマール （２０）　　ポリヒドロキシスチレン これらの結着剤は、単独であるいは２種以上の混合物と
して用いることができる。(2) Polyester (3) Methacrylic resin (4) Acrylic resin (5) Polyvinyl chloride (6) Polyvinylidene chloride (7) Polystyrene (8) Polyvinyl acetate (9) Styrene copolymer resin (for example, styrene-butadiene copolymer (10) Acrylonitrile copolymer resin (for example,
Vinylidene chloride-acrytronitrile copolymer, etc.) (11) Vinyl chloride-vinyl acetate copolymer (12)
Vinyl chloride-vinyl acetate-maleic anhydride copolymer (13) Silicone resin (14) Silicone-alkyd resin (15) Phenolic resin (e.g., phenol-formaldehyde resin, cresol formaldehyde resin, etc.) (16) Styrene-alkyd resin (17) Poly-
N-vinylcarbazole (18) polyvinyl butyral (19) polyvinyl formal (20) polyhydroxystyrene These binders can be used alone or in a mixture of two or more.

本発明の感光体は、第１図および第２図に示すように導
電性支持体ｌ上にキャリア発生物質を主成分とするキャ
リア発生層２と本発明の化合物をキャリア輸送物質の主
成分として含有するキャリア輸送層３との積層体より成
る感光層４を設ける。As shown in FIGS. 1 and 2, the photoreceptor of the present invention comprises a carrier generating layer 2 containing a carrier-generating substance as a main component on a conductive support l, and a carrier-generating layer 2 containing a carrier-generating substance as a main component and a compound of the present invention as a main component of a carrier-transporting substance. A photosensitive layer 4 made of a laminate with a carrier transport layer 3 containing the photosensitive layer 4 is provided.

第３図および第４図に示すようにこの感光層４は、導電
性支持体ｌ上に設けた中間層５を介して設けてもよい。As shown in FIGS. 3 and 4, this photosensitive layer 4 may be provided via an intermediate layer 5 provided on a conductive support l.

このように感光層４を二層構成とじたときに最もすぐれ
た電子写真特性を有する電子写真感光体が得られる。ま
た本発明においては、第５図および第６図に示すように
前記キャリア輸送物質を主成分とする層６中に微粒子状
のキャリア発生物質７を分散してなる感光層４を導電性
支持体ｌ上に直接あるいは、中間層５を介して設けても
よい。When the photosensitive layer 4 has a two-layer structure in this manner, an electrophotographic photoreceptor having the best electrophotographic properties can be obtained. Further, in the present invention, as shown in FIGS. 5 and 6, a photosensitive layer 4 formed by dispersing a carrier generating substance 7 in the form of fine particles in a layer 6 mainly composed of the carrier transporting substance is used as a conductive support. It may be provided directly on the layer 1 or via the intermediate layer 5.

更に前記感光層４の上には必要に応じ保護層８を設けて
もよい。Furthermore, a protective layer 8 may be provided on the photosensitive layer 4 if necessary.

ここで感光層４を二層構成としたときにキャリア発生層
２とキャリア輸送層３のいずれを上層とするかは、帯電
極性を正、負のいずれに選ぶかによって決定される。す
なわち負帯電型感光層とする場合は、キャリア輸送層３
を上層とするのが有利であり、これは該キャリア輸送層
３中のキャリア輸送物質が、正孔に対して高い輸送能を
有する物質であるからである。When the photosensitive layer 4 has a two-layer structure, which of the carrier generation layer 2 and the carrier transport layer 3 is to be the upper layer is determined by whether the charging polarity is positive or negative. That is, in the case of a negatively charged photosensitive layer, the carrier transport layer 3
It is advantageous to use the carrier transport layer 3 as the upper layer because the carrier transport material in the carrier transport layer 3 is a material that has a high transport ability for holes.

また、二層構成の感光層４を構成するキャリア発生層２
は、導電性支持体ｌもしくはキャリア輸送層３上に直接
あるいは必要に応じて接着層もしくはバリヤ層などの中
間層を設けた上に、次の方法によって形成することがで
きる。Further, a carrier generation layer 2 constituting a photosensitive layer 4 having a two-layer structure
can be formed directly on the conductive support l or the carrier transport layer 3 or after providing an intermediate layer such as an adhesive layer or a barrier layer if necessary, by the following method.

（１）真空蒸着法 （２）キャリア発生物質を適当な溶剤に溶解した溶液を
塗布する方法 （３）キャリア発生物質をボールミル、サンドグライン
ダー等によって分散媒中で微細粒子状とし必要に応じて
、バインダと混合分散して得られる分散液を塗布する方
法。(1) Vacuum deposition method (2) Method of applying a solution of a carrier-generating substance dissolved in a suitable solvent (3) Forming the carrier-generating substance into fine particles in a dispersion medium using a ball mill, sand grinder, etc. A method of applying a dispersion obtained by mixing and dispersing a binder.

本発明は塗布法による。The present invention is based on a coating method.

このようにして形成されるキャリア発生層２の厚さは、
０．０１μｍ〜５μｍであることが好しく、更に好しく
は０．０５μｍ〜３μｍである。The thickness of the carrier generation layer 2 formed in this way is
It is preferably 0.01 μm to 5 μm, more preferably 0.05 μm to 3 μm.

またキャリア輸送層３の厚さは、必要に応じて変更し得
るが通常５μｍ〜３０μｍであることが好しい。このキ
ャリア輸送層３における組成割合は、本発明のキャリア
輸送物質１重量部に対して結着剤０．８〜１０重量部と
するのが好しいが、微粒子状のキャリア発生物質を分散
せしめた感光層４を形成する場合は、キャリア発生物質
１重量部に対して結着剤を５重量部以下の範囲で用いる
ことが好しい。Further, the thickness of the carrier transport layer 3 can be changed as necessary, but it is usually preferably 5 μm to 30 μm. The composition ratio in this carrier transport layer 3 is preferably 0.8 to 10 parts by weight of the binder to 1 part by weight of the carrier transport material of the present invention, but it is preferable that the carrier-generating material in the form of fine particles is dispersed therein. When forming the photosensitive layer 4, it is preferable to use the binder in an amount of 5 parts by weight or less per 1 part by weight of the carrier-generating substance.

またキャリア発生層を結着剤による分散型のものとして
構成する場合には、キャリア発生物質１重量部に対して
結着剤を５重量部以下の範囲で用いることが好しい。Further, when the carrier generation layer is configured as a dispersed layer using a binder, it is preferable to use the binder in an amount of 5 parts by weight or less per 1 part by weight of the carrier generating substance.

本発明の感光体の層構成は、前記のように積層構成と単
層構成とがあるが、表面層となるキャリア輸送層、キャ
リア発生層、単層感光層または保護層のいずれか、もし
くはそれら複数層には感度の向上、残留電位ないし、反
復使用時の疲労低減等を目的として１種または２種以上
の電子受容物質を含有せしめることができる。The layer structure of the photoreceptor of the present invention includes a laminated structure and a single layer structure as described above, and the surface layer includes a carrier transport layer, a carrier generation layer, a single layer photosensitive layer, a protective layer, or both. The plurality of layers may contain one or more electron-accepting substances for the purpose of improving sensitivity, reducing residual potential, and reducing fatigue during repeated use.

また前記中間層は接着層またはバリヤ層として機能する
もので、前記結着剤樹脂のほかに、例えハホリビニルア
ルコール、エチルセルロース、カルボキシメチルセルロ
ース、カゼインなどが用いられる。Further, the intermediate layer functions as an adhesive layer or a barrier layer, and in addition to the binder resin, for example, haorivinyl alcohol, ethyl cellulose, carboxymethyl cellulose, casein, etc. are used.

本発明に於て感光層構成層の形成に用いられる溶媒とし
ては、例えばＮ、Ｎ−ジメチルホルムアミド、ベンゼン
、トルエン、キシレン、モノクロルベンゼン、ｌ、２−
ジクロロエタン、ジクロロメタン、１．１．２４リクロ
ロエタン、テトラヒドロ７ラン、メチルエチルケトン、
酢酸エチル、酢酸ブチル等を挙げることができる。In the present invention, examples of the solvent used for forming the photosensitive layer constituting layer include N,N-dimethylformamide, benzene, toluene, xylene, monochlorobenzene, l,2-
Dichloroethane, dichloromethane, 1.1.24lichloroethane, tetrahydro7ran, methyl ethyl ketone,
Examples include ethyl acetate and butyl acetate.

本発明の電子写真感光体の構成に用いられる導電性支持
体ｌとしては、主として下記のものが用いられるが、こ
れらにより限定されるものではない。As the conductive support l used in the construction of the electrophotographic photoreceptor of the present invention, the following are mainly used, but the invention is not limited thereto.

（１）　　アルミニウム板、ステンレス板などの金属板
、およびドラム形状のもの。(1) Metal plates such as aluminum plates and stainless steel plates, and drum-shaped items.

（２）祇あるいはプラスチックフィルムなどの支持体上
にアルミニウム、パラジウム、金などの金属薄層をラミ
ネートもしくは蒸着によって設けたもの。(2) A thin layer of metal such as aluminum, palladium, or gold is provided on a support such as aluminum or plastic film by lamination or vapor deposition.

（３）紙、あるいはプラスチックフィルムなどの支持体
上に導電性ポリマ、酸化インジウム、酸化スズなどの導
電性化合物の層を塗布もしくは蒸着によって設けたもの
。(3) A layer of a conductive compound such as a conductive polymer, indium oxide, or tin oxide is provided on a support such as paper or a plastic film by coating or vapor deposition.

本発明に係わるキャリア輸送層およびキャリア発生層等
の構成層の形成には、真空蒸着、スパッタリング、ＣＶ
Ｄ等の気相堆債法あるいはディッピング、スプレィ、ブ
レード、ロール法等の塗布方法が任意に用いられる。Formation of constituent layers such as a carrier transport layer and a carrier generation layer according to the present invention includes vacuum evaporation, sputtering, CV
A vapor deposition method such as D, or a coating method such as dipping, spraying, blade, or roll method may be used as desired.

本発明の感光体は以上のような構成であって、後述する
ような実施例からも明らかなように帯電特性、感度特性
、画像形成特性に優れたものである。特に反復転写式電
子写真方式に供したときにも疲労劣化が少なく耐久性が
優れたものである。The photoreceptor of the present invention has the above-mentioned structure, and has excellent charging characteristics, sensitivity characteristics, and image forming characteristics, as is clear from the examples described below. In particular, it exhibits excellent durability with little fatigue deterioration even when subjected to repeated transfer electrophotography.

〔実施例〕〔Example〕

以下本発明の実施例を具体的に説明するが、これにより
本発明の実施態様が限定されるものではない。Examples of the present invention will be specifically described below, but the embodiments of the present invention are not limited thereby.

実施例　１〜７ ポリエステルフィルム上にアルミニウム箔をラミネート
して成る導電性支持体上に、キャリア発生物質としてジ
ブロモアンスアンスロン　「モノライトレッド２Ｙ」（
化合物Ｇ　ｌ　）　（Ｃ，１，Ｎｏ５９３００．ＩＣＩ
社製）１．８重量部とポリカーボネイト樹脂「ニーピロ
ンＺ−２００Ｊ（三菱瓦斯化学（株）製）０．９重量部
とを１．２−ジクロロエタン（Ｅ　Ｄ　Ｃ）１００重量
部に加え、ボールミルで２４時間分散した液を乾燥後の
膜厚が１．０μｍになるように塗布してキャリア発生層
を形成した。Examples 1 to 7 Dibromoanthrone “Monolite Red 2Y” (
Compound G l ) (C,1, No59300.ICI
1.8 parts by weight of polycarbonate resin "Nipilon Z-200J (manufactured by Mitsubishi Gas Chemical Co., Ltd.)" were added to 100 parts by weight of 1,2-dichloroethane (EDC), and the mixture was mixed in a ball mill. A carrier generation layer was formed by applying the liquid dispersed for 24 hours so that the film thickness after drying was 1.0 μm.

化合物Ｇ−１ 次に、キャリア輸送物質として例示化合物Ｉ−１を０．
３重量部と例示化合物■−５５を９．７重量部及びポリ
カーボネイト樹脂　［ニーピロンＺ　−２００Ｊ（三菱
瓦斯化学（株）製）１５重量部とを１．２−ジクロロエ
タン１００重量部に溶解した液を乾燥後の膜厚が１５μ
ｍになるように塗布してキャリア輸送層を形成し、実施
例の電子写真感光体を作成した。Compound G-1 Next, Exemplified Compound I-1 was used as a carrier transport substance at 0.
A solution obtained by dissolving 3 parts by weight of exemplified compound ■-55, 9.7 parts by weight, and 15 parts by weight of polycarbonate resin [Niepilon Z-200J (manufactured by Mitsubishi Gas Chemical Co., Ltd.) in 100 parts by weight of 1,2-dichloroethane was prepared. Film thickness after drying is 15μ
A carrier transport layer was formed by coating the carrier in an amount of 100 m, and an electrophotographic photoreceptor of the example was prepared.

また、キャリア輸送物質として例示化合物Ｉ　−１と例
示化合物■−５５の配合比を第１表のようにした他は実
施例１と同様にして、実施例２〜７の電子写真感光体を
作成した。Further, electrophotographic photoreceptors of Examples 2 to 7 were prepared in the same manner as in Example 1, except that the compounding ratio of Exemplified Compound I-1 and Exemplified Compound ■-55 as carrier transport materials was changed as shown in Table 1. did.

比較例（１）及び（２） キャリア輸送物質として化合物Ｉ−１を単独で用いた他
は、実施例１と同様にして比較例（１）の電子写真感光
体を形成した。Comparative Examples (1) and (2) An electrophotographic photoreceptor of Comparative Example (1) was formed in the same manner as in Example 1, except that Compound I-1 was used alone as a carrier transporting substance.

またキャリア輸送物質として化合物ｌｌ−５５を単独で
用いた他は実施例１と同様にして比較例（２）の電子写
真感光体を形成した。Further, an electrophotographic photoreceptor of Comparative Example (2) was formed in the same manner as in Example 1 except that Compound 11-55 was used alone as a carrier transport material.

実施例　８〜１０ アルミニウムを蒸着したポリエステルフィルム上に塩化
ビニル−酢酸ビニル−無水マレイン酸共重合体「エスレ
ック　ＭＦ−１０Ｊ（漬水化学社製）から成る膜厚０．
１μｍの中間層を設置した。Examples 8 to 10 A film of vinyl chloride-vinyl acetate-maleic anhydride copolymer "S-LEC MF-10J (manufactured by Tsukisui Kagaku Co., Ltd.)" having a thickness of 0.5 mm was deposited on a polyester film on which aluminum was vapor-deposited.
A 1 μm intermediate layer was installed.

その上にキャリア発生物質として下記構造式で示される
ビスアゾ化合物Ｇ−２１，０重量部とポリカーボネイト
樹脂「パンライトＬ−１２５０Ｊ（奇人化成社製）０．
５重量部とを、ｌ、２−ジクロロプロパン（Ｐ　Ｄ　Ｃ
）１００重量部に加え、サンドグラインダで２時間分散
した液を乾燥後の膜厚が０．３μｍになるように塗布し
てキャリア発生層を形成した。On top of that, 1.0 parts by weight of bisazo compound G-2 shown by the following structural formula as a carrier generating substance and 0.0 parts by weight of polycarbonate resin "Panlite L-1250J (manufactured by Kijin Kasei Co., Ltd.)".
5 parts by weight of l,2-dichloropropane (PDC
), and a solution that was dispersed for 2 hours using a sand grinder was applied so that the film thickness after drying was 0.3 μm to form a carrier generation layer.

化合物Ｇ−２ その上にキャリア輸送物質として例示化合物Ｉ−３を１
．６重量部と例示化合物■−６９を８．４を置部及びポ
リカーボネイト樹脂「パンライトＫ　−１３００Ｊ（奇
人化成社製）１８重量部とを、１，２−ジクロロプロパ
ン　１００重量部に溶解した液を乾燥後の膜厚が１８μ
ｍになるように塗布してキャリア輸送層を形成し、実施
例８の電子写真感光体を形成した。Compound G-2 and Exemplified Compound I-3 as a carrier transport substance thereon.
．． A solution prepared by dissolving 6 parts by weight of exemplified compound ■-69 in 100 parts by weight of 1,2-dichloropropane and 18 parts by weight of polycarbonate resin "Panlite K-1300J (manufactured by Kijin Kasei Co., Ltd.)" The film thickness after drying is 18μ
A carrier transport layer was formed by coating the film in an amount of 100 m, and an electrophotographic photoreceptor of Example 8 was formed.

またキャリア輸送物質として第１表に示すような化合物
の組合せを用いた他は、実施例８と同様にして実施例９
及びＩＯの電子写真感光体を形成しｔこ。In addition, Example 9 was carried out in the same manner as in Example 8, except that the combination of compounds shown in Table 1 was used as the carrier transport substance.
and forming an IO electrophotographic photoreceptor.

比較例（３）及び（４） キャリア輸送物質として化合物Ｉ−３を単独で用いた他
は、実施例８と同様にして比較例（３）の電子写真感光
体を形成した。Comparative Examples (3) and (4) An electrophotographic photoreceptor of Comparative Example (3) was formed in the same manner as in Example 8, except that Compound I-3 was used alone as a carrier transporting substance.

またキャリア輸送物質として化合物ｎ−６９を単独で用
いた他は実施例８と同様にして比較例（４）の電子写真
感光体を形成した。Further, an electrophotographic photoreceptor of Comparative Example (4) was formed in the same manner as in Example 8 except that compound n-69 was used alone as a carrier transporting substance.

実施例　１１−１３ アルミニウムを蒸着したポリエステルフィルム上に、キ
ャリア発生物質として下記構造式で示されるビスアゾ化
合物Ｇ−３１，２重量部とポリカーボネイト樹脂「パン
ライトＬ−１２５０Ｊ　（奇人化成社製）０．６重量部
とをテトラヒドロ７ラン（ＴＨＦ）１００重量部に加え
、サンドグラインダにて８時間分散した液を乾燥後の膜
厚が０．２μｍになるように塗布してキャリア発生層を
形成した。Example 11-13 On a polyester film on which aluminum was vapor-deposited, 2 parts by weight of bisazo compound G-31 shown by the following structural formula as a carrier generating substance and 0.2 parts by weight of polycarbonate resin "Panlite L-1250J (manufactured by Kijin Kasei Co., Ltd.)" were added. 6 parts by weight were added to 100 parts by weight of tetrahydro-7 run (THF), and the solution was dispersed for 8 hours using a sand grinder, and then applied so that the film thickness after drying was 0.2 μm to form a carrier generation layer.

化合物Ｇ−３ 次に、キャリア輸送物質として、例示化合物ニー２８を
１．９重量部と例示化合物Ｉ［−３０を８．１重量部及
びポリカーボネイト樹脂「パンラニイトＫ　−１３００
Ｊ（音大化成社製）１５重量部とをテトラヒドロフラン
１００重量部に溶解した液を乾燥後の膜厚が１５μｍに
なるように塗布してキャリア輸送層を形成し、実施例１
１の電子写真感光体を作成した。Compound G-3 Next, as a carrier transport substance, 1.9 parts by weight of Exemplified Compound Ni 28, 8.1 parts by weight of Exemplified Compound I[-30, and polycarbonate resin "Panranite K-1300" were added.
A carrier transport layer was formed by applying a solution prepared by dissolving 15 parts by weight of J (manufactured by Ondai Kasei Co., Ltd.) in 100 parts by weight of tetrahydrofuran so that the film thickness after drying was 15 μm.
An electrophotographic photoreceptor of No. 1 was prepared.

また、キャリア輸送物質として第１表に示すような化合
物の組合せを用いた他は、実施例１１と同様にして実施
例１２及び１３の電子写真感光体を形成し　ｔこ　。Further, electrophotographic photoreceptors of Examples 12 and 13 were formed in the same manner as in Example 11, except that the combinations of compounds shown in Table 1 were used as carrier transport materials.

比較例（５）及び（６） キャリア輸送物質として化合物ｌ−２８を単独で用いた
他は、実施例１１と同様にして比較例（５）の電子写真
感光体を形成した。Comparative Examples (5) and (6) An electrophotographic photoreceptor of Comparative Example (5) was formed in the same manner as in Example 11, except that Compound 1-28 was used alone as a carrier transporting substance.

まＩ；、キャリア輸送物質として化合物ｎ　−３０を単
独で用いた他は実施例１１と同様にして比較例（６）の
電子写真感光体を形成した。An electrophotographic photoreceptor of Comparative Example (6) was formed in the same manner as in Example 11 except that Compound n-30 was used alone as a carrier transport material.

実施例　１４〜１６ アルミニウムを蒸着したポリエステルフィルム上に、キ
ャリア輸送物質として下記構造式で示されるＸ型無金属
７タロシアニン　（化合物Ｇ−４）（大日本インキ化学
（株）製）２．０重量部とポリメチルメタクリレート樹
脂［エルバサイト２００８Ｊ　（デュポン社製）２．０
重量部とを１．２−ジクロロエタン１００重量部に溶解
した液を乾燥後の膜厚が０．２μｍになるように塗布し
てキャリア発生層を形成した。Examples 14 to 16 On a polyester film on which aluminum was vapor-deposited, X-type metal-free 7-thalocyanine (compound G-4) (manufactured by Dainippon Ink Chemical Co., Ltd.) 2.0 weight shown by the following structural formula was applied as a carrier transport substance. and polymethyl methacrylate resin [Elvacite 2008J (manufactured by DuPont) 2.0
A carrier-generating layer was formed by dissolving 100 parts by weight of 1,2-dichloroethane and applying a solution having a dry film thickness of 0.2 μm.

化合物Ｇ−４ 次にキャリア輸送物質として、例示化合物Ｉ　−４０を
０．６重量部と例示化合物ｎ−４８を９．４重量部及び
ポリメチルメタクリレート樹脂［エルバサイト２０１０
Ｊ　（デュポン社製）１５重量部とを１．２−ジクロロ
エタン１００重量部に溶解した液を乾燥後の膜厚が１８
μｍになるように塗布して実施例１４の電子写真感光体
を形成しｔ；。Compound G-4 Next, as carrier transport substances, 0.6 parts by weight of Exemplified Compound I-40, 9.4 parts by weight of Exemplified Compound n-48, and polymethyl methacrylate resin [Elvasite 2010
J (manufactured by DuPont) in 100 parts by weight of 1,2-dichloroethane, the film thickness after drying was 18.
The electrophotographic photoreceptor of Example 14 was formed by coating to a thickness of μm.

また、キャリア輸送物質として第１表に示すような化合
物の組合せを用いた他は、実施例１４と同様にして実施
例１５及び１６の電子写真感光体を形成し　ｌこ　。Further, electrophotographic photoreceptors of Examples 15 and 16 were formed in the same manner as in Example 14, except that the combinations of compounds shown in Table 1 were used as carrier transport materials.

比較例（７）及び（８） キャリア輸送物質として化合物ｌ−４０を単独で用いた
他は、実施例１４と同様にして比較例（７）の電子写真
感光体を形成した。Comparative Examples (7) and (8) An electrophotographic photoreceptor of Comparative Example (7) was formed in the same manner as in Example 14, except that Compound 1-40 was used alone as the carrier transport material.

また、キャリア輸送物質として化合物■−４８を単独で
用いた他は実施例１４と同様にして比較例（８）の電子
写真感光体を形成した。Further, an electrophotographic photoreceptor of Comparative Example (8) was formed in the same manner as in Example 14 except that Compound 1-48 was used alone as a carrier transporting substance.

次に、本発明の実施例１−１６の電子写真感光体と比較
例（１）〜（８）の電子写真感光体について静電複写紙
試験装置ｒＥ　Ｐ　Ａ　−８１００Ｊ　（川口電機製作
新製）を用いてスタティック方式で電子写真特性を測定
した。Next, the electrophotographic photoreceptors of Examples 1 to 16 of the present invention and the electrophotographic photoreceptors of Comparative Examples (1) to (8) were tested using an electrostatic copying paper tester rE P A -8100J (newly manufactured by Kawaguchi Denki). The electrophotographic properties were measured using a static method.

即ち、ラインスピードを２５０ｍｍ／　ｓｅｅに設定し
、５０ｆｆａｘの前露光を２秒間照射したあと、−６Ｋ
Ｖにて帯電を行い帯電後５秒間暗減衰させたあとの表面
電位を帯電電位Ｖａとし、その後、２Ｑｕｘの白色光を
１０秒間照射したあとの表面電位を残留電位Ｖｒとし、
Ｖａ及びＶｒを測定した。That is, after setting the line speed to 250 mm/see and pre-exposure at 50 ffax for 2 seconds, -6K
The surface potential after charging at V and dark decay for 5 seconds after charging is taken as the charging potential Va, and the surface potential after being irradiated with 2 Qux white light for 10 seconds is taken as the residual potential Vr.
Va and Vr were measured.

また、この測定を１０，０００回繰返して行った。Moreover, this measurement was repeated 10,000 times.

結果は第１表に示す通りである。The results are shown in Table 1.

また溶解性については、目視により室温分散溶媒に良好
に溶解するものをＯ１然らざるものを×として評価した
。Regarding solubility, those that were visually observed to dissolve well in the room temperature dispersion solvent were evaluated as O1 and those that were not good were evaluated as ×.

実施例と比較例の電子写真特性の比較 第１表に示すように本発明の実施例１〜７の電子写真感
光体は比較例（１）、（２）の電子写真感光体と比較し
て、繰返し使用時の帯電電位の変化が少なく、かつ残留
電位の上昇も少ないことから繰返し使用時の耐久性に優
れていることがわかる。Comparison of electrophotographic properties of Examples and Comparative Examples As shown in Table 1, the electrophotographic photoreceptors of Examples 1 to 7 of the present invention had better performance compared to the electrophotographic photoreceptors of Comparative Examples (1) and (2). It can be seen that the durability during repeated use is excellent because there is little change in charging potential during repeated use and little increase in residual potential.

また、一般式〔Ｉ〕で示されるキャリア輸送物質と一般
式〔ＩＩ〕で示されるキャリア輸送物質の混合比が３：
９７から９７：３の範囲で繰返し使用時の耐久性の向上
効果が認められることと、前記キャリア輸送物質の混合
比が７：９３から５０＋５０の範囲では耐久性の向上効
果が特に大きく、より好ましい範囲であることがわかる
。Further, the mixing ratio of the carrier transport substance represented by general formula [I] and the carrier transport substance represented by general formula [II] is 3:
It is more preferable that the effect of improving durability during repeated use is observed in the range of 97 to 97:3, and that the effect of improving durability during repeated use is particularly large when the mixing ratio of the carrier transport substance is in the range of 7:93 to 50 + 50. It can be seen that the range is within the range.

さらに、同様にして実施例８〜ｌＯと比較例（３）。Furthermore, Examples 8 to 1O and Comparative Example (3) were similarly prepared.

（４）を比較した場合、及び実施例１１〜１３と比較例
（５）、（６）を比較した場合、及び実施例１４〜１６
と比較例（７）、（８）を比較した場合にも、各々の比
較に対して、実施例の電子写真感光体の方が比較例の電
子写真感光体より繰返し使用時の帯電電位の変化が少な
く、しかも残留電位の上昇も少なく、特性が安定してい
ることがわかる。(4), and Examples 11 to 13 and Comparative Examples (5) and (6), and Examples 14 to 16.
When Comparative Examples (7) and (8) are compared, the electrophotographic photoreceptor of the example has a higher change in charging potential during repeated use than the electrophotographic photoreceptor of the comparative example for each comparison. It can be seen that the characteristics are stable, with little increase in residual potential.

以上の結果より、一般式〔Ｉ〕で示されるキャリア輸送
物質と一般式（ｎ）で示されるキャリア輸送物質を混合
して用いることによる本発明の電子写真感光体の耐久性
向上効果が明らかである。From the above results, it is clear that the durability improvement effect of the electrophotographic photoreceptor of the present invention is achieved by using a mixture of the carrier transporting substance represented by the general formula [I] and the carrier transporting substance represented by the general formula (n). be.

また一般式（Ｉｆ）で示されるスチル化合物の一般式〔
■〕で示される化合物に対する溶解促進効果が明かに認
められる。Further, the general formula of the still compound represented by the general formula (If) [
(2) The dissolution promoting effect on the compound shown in [2] is clearly observed.

・二二 以下余白・22 Margin below

【図面の簡単な説明】 第１図〜第６図はそれぞれ本発明の感光体の機械的構成
例について示す断面図である。 ■・・・導電性支持体 ２・・・キャリア発生層 ３・・・キャリア輸送層 ４・・・感光層 ５・・・中間層 ６・・・キャリア輸送物質を含有する層７・・・キャリ
ア発生物質 ８・・・保護層 出願人　小西六写真工業株式会社BRIEF DESCRIPTION OF THE DRAWINGS FIGS. 1 to 6 are cross-sectional views showing examples of the mechanical structure of the photoreceptor of the present invention. ■... Conductive support 2... Carrier generation layer 3... Carrier transport layer 4... Photosensitive layer 5... Intermediate layer 6... Layer containing carrier transport substance 7... Carrier Generated substance 8...Protective layer applicant Konishiroku Photo Industry Co., Ltd.

Claims (1)

【特許請求の範囲】 導電性支持体上に下記一般式〔 I 〕で示される化合物
の少なくともひとつと、下記一般式〔II〕で示される化
合物の少くとも１つとを含有する感光層を有することを
特徴とする電子写真感光体。 一般式〔 I 〕 ▲数式、化学式、表等があります▼ 一般式〔II〕 ▲数式、化学式、表等があります▼ 〔但し式中、Ａｒ＿１、Ａｒ＿２、Ａｒ＿３及びＡｒ＿
９は置換、未置換のアリーレン基を表し、Ａｒ＿４、Ａ
ｒ＿５、Ａｒ＿６、Ａｒ＿７、Ａｒ＿８及びＡｒ＿１＿
０は置換、未置換のアリール基、芳香族置換アルキル基
及び置換、未置換の複素環基を表し、Ｒ＿１、Ｒ＿２、
Ｒ＿３、Ｒ＿４及びＲ＿５は、水素原子、置換、未置換
のアルキル基、置換、未置換のアリール基を表す。〕[Scope of Claims] A photosensitive layer containing at least one compound represented by the following general formula [I] and at least one compound represented by the following general formula [II] on a conductive support. An electrophotographic photoreceptor featuring: General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ General formula [II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, in the formula, Ar_1, Ar_2, Ar_3, and Ar_
9 represents a substituted or unsubstituted arylene group, Ar_4, A
r_5, Ar_6, Ar_7, Ar_8 and Ar_1_
0 represents a substituted or unsubstituted aryl group, an aromatic substituted alkyl group, or a substituted or unsubstituted heterocyclic group, R_1, R_2,
R_3, R_4 and R_5 represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. ]
JP26320987A 1987-10-19 1987-10-19 Electrophotographic sensitive body Pending JPH01105955A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP26320987A JPH01105955A (en) 1987-10-19 1987-10-19 Electrophotographic sensitive body

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP26320987A JPH01105955A (en) 1987-10-19 1987-10-19 Electrophotographic sensitive body

Publications (1)

Publication Number Publication Date
JPH01105955A true JPH01105955A (en) 1989-04-24

Family

ID=17386297

Family Applications (1)

Application Number Title Priority Date Filing Date
JP26320987A Pending JPH01105955A (en) 1987-10-19 1987-10-19 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPH01105955A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08295655A (en) * 1995-03-01 1996-11-12 Takasago Internatl Corp Triphenylamine derivative, charge transport material and photosensitizer for electrophotograph using the same
JPH10255979A (en) * 1997-03-06 1998-09-25 Minolta Co Ltd Organic electroluminescent element
WO2001059030A1 (en) * 2000-02-09 2001-08-16 Isis Innovation Limited Dendrimers
WO2002066575A1 (en) * 2001-02-20 2002-08-29 Isis Innovation Limited Asymmetric dendrimers
WO2006000388A1 (en) * 2004-06-26 2006-01-05 Merck Patent Gmbh Organic electroluminescent device
JP2008120770A (en) * 2005-12-27 2008-05-29 Kyocera Mita Corp Triarylamine derivative and electrophotographic photoreceptor
US7592074B2 (en) 2001-02-20 2009-09-22 Isis Innovation Limited Metal-containing dendrimers
US7632576B2 (en) 2001-02-20 2009-12-15 Isis Innovation Limited Aryl-aryl dendrimers
US7817927B2 (en) 2006-08-29 2010-10-19 Brother Kogyo Kabushiki Kaisha Image forming apparatus with developer collection
JP2011033792A (en) * 2009-07-31 2011-02-17 Ricoh Co Ltd Electrophotographic photoreceptor

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08295655A (en) * 1995-03-01 1996-11-12 Takasago Internatl Corp Triphenylamine derivative, charge transport material and photosensitizer for electrophotograph using the same
JPH10255979A (en) * 1997-03-06 1998-09-25 Minolta Co Ltd Organic electroluminescent element
WO2001059030A1 (en) * 2000-02-09 2001-08-16 Isis Innovation Limited Dendrimers
US7960725B2 (en) 2001-02-20 2011-06-14 Isis Innovation Limited Aryl-aryl dendrimers
US7537842B2 (en) 2001-02-20 2009-05-26 Isis Innovation Limited Asymmetric dendrimers
US7592074B2 (en) 2001-02-20 2009-09-22 Isis Innovation Limited Metal-containing dendrimers
US7632576B2 (en) 2001-02-20 2009-12-15 Isis Innovation Limited Aryl-aryl dendrimers
US7906902B2 (en) 2001-02-20 2011-03-15 Isis Innovation Limited Metal-containing dendrimers
WO2002066575A1 (en) * 2001-02-20 2002-08-29 Isis Innovation Limited Asymmetric dendrimers
US7960557B2 (en) 2001-02-20 2011-06-14 Isis Innovation Limited Asymmetric dendrimers
US8314549B2 (en) 2001-02-20 2012-11-20 Isis Innovation Limited Metal-containing dendrimers
US8319213B2 (en) 2001-02-20 2012-11-27 Isis Innovation Limited Aryl-aryl dendrimers
WO2006000388A1 (en) * 2004-06-26 2006-01-05 Merck Patent Gmbh Organic electroluminescent device
JP2008120770A (en) * 2005-12-27 2008-05-29 Kyocera Mita Corp Triarylamine derivative and electrophotographic photoreceptor
US7817927B2 (en) 2006-08-29 2010-10-19 Brother Kogyo Kabushiki Kaisha Image forming apparatus with developer collection
JP2011033792A (en) * 2009-07-31 2011-02-17 Ricoh Co Ltd Electrophotographic photoreceptor

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