JPS59104653A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPS59104653A
JPS59104653A JP57214034A JP21403482A JPS59104653A JP S59104653 A JPS59104653 A JP S59104653A JP 57214034 A JP57214034 A JP 57214034A JP 21403482 A JP21403482 A JP 21403482A JP S59104653 A JPS59104653 A JP S59104653A
Authority
JP
Japan
Prior art keywords
group
substituted
unsubstituted
general formula
formula
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
JP57214034A
Other languages
Japanese (ja)
Other versions
JPH0120421B2 (en
Inventor
Yoshihide Fujimaki
藤巻 義英
Yoshiaki Takei
武居 良明
Hiroyuki Nomori
野守 弘之
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 JP57214034A priority Critical patent/JPS59104653A/en
Priority to US06/549,601 priority patent/US4540651A/en
Publication of JPS59104653A publication Critical patent/JPS59104653A/en
Publication of JPH0120421B2 publication Critical patent/JPH0120421B2/ja
Granted legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622Heterocyclic compounds
    • G03G5/0624Heterocyclic compounds containing one hetero ring
    • G03G5/0627Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0629Heterocyclic compounds containing one hetero ring being five-membered containing one hetero atom
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0612Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614Amines
    • G03G5/06142Amines arylamine
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0612Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614Amines
    • G03G5/06142Amines arylamine
    • G03G5/06144Amines arylamine diamine
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0612Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614Amines
    • G03G5/06142Amines arylamine
    • G03G5/06147Amines arylamine alkenylarylamine
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0612Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614Amines
    • G03G5/06142Amines arylamine
    • G03G5/06147Amines arylamine alkenylarylamine
    • G03G5/061473Amines arylamine alkenylarylamine plural alkenyl groups linked directly to the same aryl group
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0612Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0616Hydrazines; Hydrazones
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622Heterocyclic compounds
    • G03G5/0624Heterocyclic compounds containing one hetero ring
    • G03G5/0635Heterocyclic compounds containing one hetero ring being six-membered
    • G03G5/0637Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664Dyes
    • G03G5/0666Dyes containing a methine or polymethine group
    • G03G5/0668Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664Dyes
    • G03G5/0666Dyes containing a methine or polymethine group
    • G03G5/0668Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664Dyes
    • G03G5/0675Azo dyes
    • G03G5/0679Disazo dyes
    • G03G5/0683Disazo dyes containing polymethine or anthraquinone groups
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664Dyes
    • G03G5/0675Azo dyes
    • G03G5/0679Disazo dyes
    • G03G5/0683Disazo dyes containing polymethine or anthraquinone groups
    • G03G5/0685Disazo dyes containing polymethine or anthraquinone groups containing hetero rings in the part of the molecule between the azo-groups

Abstract

PURPOSE:To obtain always a good copied image with high sensitivity without any accumulation of potential even during repeated uses by incorporating a specified bisazo compd. in a carrier generating layer and a specified styryl compd. and an amino deriv. in a carrier transfer layer. CONSTITUTION:A carrier generating layer incorporates a compd. represented by formula I or II in which Ar1, Ar2, Ar3 are optionally substd. aromatic carbon rings; R1, R2 are electron acceptor groups, such as CN; A is one of groups represented by formulae III-V, or the like; X is OH, optionally substd. amino, or the like; A' is optionally substd. aryl; Y is H, halogen, optionally substd. alkyl, or the like; Z is an atomic group constituting an optionally substd. aromatic carbon or hetero ring; R3 is H, optionally substd. amino, COOH, or the like; n is 1 or 2; and m is 0-4. A carrier transfer layer incorporates a compd. represented by formula VI or VII in which R7, R8 are each optionally substd. alkyl or phenyl; R9 is optionally substd. phenyl, naphthyl, heterocyclic, or the like; R10-R13 are each H, halogen, or the like. Thus, a photosensitive body of long life is obtained.

Description

【発明の詳細な説明】 本発明は、導電性支持体上に、キャリア発生相とキャリ
ア輸送相とを組合せて成る感光層を設けた電子写真感光
体に関するものである。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor in which a photosensitive layer comprising a combination of a carrier generation phase and a carrier transport phase is provided on a conductive support.

現在までに、可視光を吸収して荷電キャリア(以下単に
「キャリア」という。)を発生1−るキャリア発生物質
(以下I CGMJという。)を含有して成るキャリア
発生層(以下[CGLJという。)と、このCGLにお
いて発生した正又は負のキャリアの何れか一方又は両方
を輸送するキャリア輸送物質(以下I C’l’MJと
いう。)を含有して成るキャリア帖1送層(以下l C
TLJという、、)とを組合せることにより、電子写真
感光体の感光層を構成せしめることが提案されている。
Until now, a carrier generation layer (hereinafter referred to as [CGLJ]) is formed by containing a carrier generation substance (hereinafter referred to as ICGMJ) that absorbs visible light and generates charge carriers (hereinafter simply referred to as "carriers"). ) and a carrier transporting material (hereinafter referred to as IC'l'MJ) that transports either or both of the positive and negative carriers generated in this CGL (hereinafter referred to as IC'l'MJ).
It has been proposed that the photosensitive layer of an electrophotographic photoreceptor is formed by combining TLJ and TLJ.

このように、キャリアの発生と、その輸送という感光層
におい工必要な2つの基礎的機能を、別個の層に分担せ
しめることにより、感光層の構成に用い得る物質の選択
範囲が広範となる上、各機能を最適に果す物質又は物質
系を独立に選定することが可能となり、又そうすること
により、電子写真プロ七スにおいて要求される緒特性、
倒置−ば帯電せしめたときの表面電位が凝1く、電荀保
持能が大きく、光感度が茜く、又反復使用における安定
性が大きい等の優れた特性を有する電子写真感光体を構
成せしめることが可能となる。
In this way, by assigning the two basic functions of carrier generation and carrier transport, which are necessary for photosensitive layer fabrication, to separate layers, the range of materials that can be used in the composition of the photosensitive layer can be widened. , it becomes possible to independently select materials or material systems that optimally perform each function, and by doing so, it is possible to independently select materials or material systems that optimally perform each function.
It constitutes an electrophotographic photoreceptor having excellent properties such as a low surface potential when charged upside down, high charge retention capacity, high photosensitivity, and high stability during repeated use. becomes possible.

従来このような感光層としては、例えば次のようなもの
が知られている。
Conventionally, as such a photosensitive layer, the following ones are known, for example.

(1)無定形セレン又は側止カドミウムより成るCGL
ど、ポリ−N−ビニルカルバゾールより成るCTLとを
積層せしめた構成。
(1) CGL made of amorphous selenium or side-stop cadmium
A structure in which CTLs made of poly-N-vinylcarbazole are laminated.

(2)  無定形セレン又は硫化カドミウムより成るC
61.と、2,4.7−ドリニトロー9−フルオレノン
を含有するC’i”Lとな積重ねせしめた構成。
(2) C consisting of amorphous selenium or cadmium sulfide
61. and C'i''L containing 2,4,7-dolinitro-9-fluorenone.

(3)  ペリレン誘導体より成るCGLと、オキサジ
アゾール誘導体を含有するCTLとを積層せしめた構成
(米国特許第3871882号明細書径照)。
(3) A structure in which a CGL made of a perylene derivative and a CTL containing an oxadiazole derivative are laminated (see US Pat. No. 3,871,882).

(4;  クロルダイヤンブルー又はメチルスカリリウ
ムより成るCGLと、ピラゾリン訪導体を含有するCT
Lとな積層せしめた構成(特開昭51−90827号公
報参照)。
(4; CT containing CGL consisting of chlordiane blue or methylscalyllium and pyrazoline visiting conductor
A structure in which the layers are stacked in an L shape (see Japanese Patent Laid-Open No. 51-90827).

(5)無定形セレン又はその合金より成るCGLと、ボ
リアリールアルカン系芳香族アミノ化合物を含有するC
TLとを積層せしめた構成(特願昭52−147251
号明細書)。
(5) CGL made of amorphous selenium or its alloy and C containing a polyarylalkane aromatic amino compound
Laminated structure with TL (Patent application 147251/1989)
No. Specification).

(6)ペリレン誘導体を含有するCGLと1.l−’ 
リアリールアルカン系芳香族アミン化合物を含有するC
 T Lとを積層せしめた構成(特願昭53−1990
7号明細咽、)。
(6) CGL containing a perylene derivative and 1. l-'
C containing a realylalkane aromatic amine compound
A structure in which T and L are laminated (Patent application 1987-1990)
No. 7 specification,).

このようにこの種の感光層としては多くのものが知られ
てはいるが、斯かる感光層を有する従来の電子写真感光
体においては反復して電子写真プロセスに供したときの
感光層の電気的疲労が激しくて使用寿命が非富に短い欠
点を有する。
As described above, many types of photosensitive layers are known, but in conventional electrophotographic photoreceptors having such photosensitive layers, the electricity of the photosensitive layer when repeatedly subjected to electrophotographic processes is limited. It has the disadvantage of severe mechanical fatigue and extremely short service life.

例えば、繰り返し′CC電子写真プロススC供したとき
に、当該電子写真感光体の電位のIs歴状態が安定に維
持されず、安定した画像形成特性を得ることができない
For example, when the electrophotographic process C is repeatedly applied, the Is history state of the potential of the electrophotographic photoreceptor is not stably maintained, making it impossible to obtain stable image forming characteristics.

また、特定のビスアゾ化合物なCGMとして用いること
が例えば特開昭55−117151号公報、特開昭54
−145142号公報等に開示されているが、このCG
1〜1と組合せ得るとされているCTMとの組合せにお
いても、なお上述の欠点か相当に大きい。
In addition, specific bisazo compounds can be used as CGMs, for example, in JP-A-55-117151 and JP-A-54.
Although it is disclosed in Publication No.-145142, etc.
Even in combination with CTM, which is said to be able to be combined with 1 to 1, the above-mentioned drawbacks are still considerable.

このことからも理解されるように、ある特定のキャリア
発生物質に対して有効なキャリア輸送物質が、他のキャ
リア発生物質に対して常に有効な訳ではなく、又特定の
キャリア輸送物質に対して有効なキャリア発生物質が、
他のキャリア軸道物質に対して常に有効であるとも言う
ことはできない。
As can be understood from this, a carrier transporting substance that is effective against a specific carrier-generating substance is not always effective against other carrier-generating substances, and An effective carrier generating substance is
It cannot be said that it is always effective for other carrier axis substances.

両物質の場合ぜが不適当な場合には電子写真感度が低く
なるはかりでなく、特に低電界時の放11、効率が悪(
・ため、所謂残留゛電位が大きくなり、最悪の場合(・
コは反稜して使用する度に電位が溜積し、実用上電子写
泗の用途に供し得なくなる。
In the case of both materials, if the mixture is inappropriate, the electrophotographic sensitivity will not only be low, but also the emission efficiency will be poor (11) especially at low electric fields.
・As a result, the so-called residual potential increases, and in the worst case (・
Each time it is used in a crooked manner, a potential accumulates, making it practically unusable for electronic photographic purposes.

このようにキャリア発生相の構成物質とキャリア輸送用
の朽成物彌との好適な組合せについては法則的な選択手
段はなく、多くの物質詳の中からイj利なわ」台ぜを実
践的に決′Jピする必要がある。
In this way, there is no lawful way to select a suitable combination of the constituent materials of the carrier generation phase and the decomposed material for carrier transport, and there are many material details to choose from in a practical manner. It is necessary to make a decision.

本発明は、キャリア発生相どキャリア4・fit送相と
を組合せて成る感光層を具え、大きな感度を有し、しか
も繰り返して電子写真プロセスに供したときにも電位の
履歴状態が安定に維持され、常に良好な可視画像を形成
することのできる電子写真感光体を提供することを目的
とする。
The present invention has a photosensitive layer that combines a carrier generation phase and a carrier 4 fit phase, has high sensitivity, and maintains a stable potential history state even when repeatedly subjected to an electrophotographic process. An object of the present invention is to provide an electrophotographic photoreceptor that can always form good visible images.

以上の目的は、キャリア発生相とキャリア輸送用とを組
合せて成る感光層を導電性支持体上に設けて成る電子写
真感光体において、前記キャリア発生相が下記一般式C
I)または一般式〔I′〕で示されるビスアゾ化合物を
含有し、前記キャリア輸送用が下記一般式[l11)で
示されるスチリル化合物及び下記一般式[1[I)で示
されるアミン誘導体の少なくとも一方を含有することを
特徴とする電子写真感光体によって達成される。
The above object is to provide an electrophotographic photoreceptor in which a photosensitive layer consisting of a combination of a carrier generation phase and a carrier transport layer is provided on a conductive support, wherein the carrier generation phase has the following general formula C.
I) or a bisazo compound represented by the general formula [I'], and the carrier transporting material is at least a styryl compound represented by the following general formula [111] and an amine derivative represented by the following general formula [1[I]. This is achieved by an electrophotographic photoreceptor characterized by containing one of the two.

一般式〔I〕 R・1 A−N=N−Ar 1−CH−c−Ar 2−CI−i
=cH−Ar 5−N=N−A一般式〔I′〕 〔式中。
General formula [I] R・1 A-N=N-Ar 1-CH-c-Ar 2-CI-i
=cH-Ar 5-N=NA General formula [I'] [In the formula.

Ar1.Ar2およ(7Ar3’それぞれ置換、未置換
の炭素環式芳香族環基。
Ar1. Ar2 and (7Ar3' are respectively substituted and unsubstituted carbocyclic aromatic ring groups.

川またはR2:それぞれ電子吸引性基、Y:水素原子、
ハロゲン原子、置換、 未置換のアルキル基、アルコキシ 基、カルボキシル基、スルホ基、 置換、未置換のカルバモイル基ま たは置換、未置換のスルファモイ ル基、(但し、mが2以上のとき は、互に異なる基であってもよい。) Z:置換、未置換の炭素環式芳香族環または置換、未置
換の複素環式芳香 族環を構成するに必要な原子群、 R3:水素原子、置換、未置換のアミノ基、置換、未置
換のカルバモイル基、 カルホキシル基またはそのエステ ル基。
River or R2: each electron-withdrawing group, Y: hydrogen atom,
Halogen atoms, substituted or unsubstituted alkyl groups, alkoxy groups, carboxyl groups, sulfo groups, substituted or unsubstituted carbamoyl groups, or substituted or unsubstituted sulfamoyl groups, (however, when m is 2 or more, mutually different ) Z: atomic group necessary to constitute a substituted or unsubstituted carbocyclic aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring, R3: hydrogen atom, substituted or unsubstituted Substituted amino group, substituted or unsubstituted carbamoyl group, carboxyl group or ester group thereof.

A′:置換、未置換のアリール基、 n :lまたは2の整数、 m :0〜4の整数を表わす。〕 一般式〔■〕 〔式中、R7、■(8:置換、未置換のアルキル基、フ
ェニル基を表わし、置換基としてはア ルキル基、アルコキシ基、フェニ ル基を用いる8 R9:置換、未置換のフェニル基、ナフチル基、アント
リル基、フルオレ ニル基または複素環基を表わし、 置換基としてはアルキル基、アル コキシ基、ハロゲン原子、水酸基、 フェニル基を用いる。
A': substituted or unsubstituted aryl group, n: an integer of 1 or 2, m: an integer of 0 to 4. ] General formula [■] [In the formula, R7, ■ (8: represents a substituted or unsubstituted alkyl group or phenyl group, and the substituent is an alkyl group, an alkoxy group, or a phenyl group 8 R9: substituted or unsubstituted represents a phenyl group, naphthyl group, anthryl group, fluorenyl group, or a heterocyclic group, and as a substituent, an alkyl group, an alkoxy group, a halogen atom, a hydroxyl group, or a phenyl group is used.

R1o=R1s :水素原子、ハロゲン原子、アルキル
基、アルコキシ基またはアルキ ルアミノ基を表わす。) 一般式[I[[) 式中、 A r 4、Ar5:置換、未置換のフェニル基を表わ
し、置換基としてはハロゲン原子、 アルキル基、ニトロ基、アルコキ シ基を用いる。
R1o=R1s: represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkylamino group. ) General formula [I[[) In the formula, A r 4, Ar 5 represents a substituted or unsubstituted phenyl group, and a halogen atom, an alkyl group, a nitro group, or an alkoxy group is used as a substituent.

Ar6:置換、未置換のフェニル基、ナフチル基、アン
トリル基、フルオレ ニル基、複素環基を表わし、置換 基としてはアルキル基、アルコキ シ基、ハロゲン原子、水酸基、ア リールオキシ基、アリール基、ア ミノ基、ニトロ基、ピペリジノ基、 モルホリノ基、ナフチル基、アン スリル基及び置換アミン基を用い る。但し、置換アミン・基の置換基 としてアシル基、アルキル基、ア リール基、アラルキル基を用いる。〕 前記一般式CI’)または一般式〔1′〕で示されるビ
スアゾ化合物のうち、好ましいのは次の一般式[Ta)
または一般式CI’a:lで示されるものである。
Ar6: represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group, fluorenyl group, or heterocyclic group, and substituents include an alkyl group, an alkoxy group, a halogen atom, a hydroxyl group, an aryloxy group, an aryl group, an amino group, Nitro groups, piperidino groups, morpholino groups, naphthyl groups, anthryl groups and substituted amine groups are used. However, an acyl group, an alkyl group, an aryl group, or an aralkyl group is used as a substituent for the substituted amine/group. ] Among the bisazo compounds represented by the general formula CI') or the general formula [1'], the following general formula [Ta) is preferred.
Or it is represented by the general formula CI'a:l.

一般式(Ia’ll N 薯 A−N=N−Ar1−CIt−CAr2 cH=ct(
Ar5 N=N−AA−N=N−Ar1−CIl=C−
Ar 2−C=(ll−Ar 3−N=IN −A〔式
中、 Ar1、Ar2、Ar5+6よびAニ一般式CI)また
は一般式〔I′〕において定義さ第1たも のと同じである。〕 更に☆イましいものは、特に次の一般式Clb)または
しI’b)で示されるものである。
General formula (Ia'll N 薯AN=N-Ar1-CIt-CAr2 cH=ct(
Ar5 N=N-AA-N=N-Ar1-CIl=C-
Ar2-C=(ll-Ar3-N=IN-A [wherein Ar1, Ar2, Ar5+6 and A general formula CI) or the same as the first one defined in general formula [I'] . ] Even more preferred are those represented by the following general formula Clb) or I'b).

一般式〔1b〕 N A−N=N−Ar 7−C11=C−Ar8−CI−1
=Ckl−A r 9−N=N −A〔式中、 Aニ一般式しI〕または一般式〔I/〕においてス酸芒
れたものと同じ、 Ar7 、ArBおよびM、:置換、未駈挾のフェニル
基を表わし、獣扱基としては、メチル基、 エチル基、などのアルキル糸、メ トキシ基、エトキシ基などのアル コキシ基、塩素原子、臭素原子な どのハロゲン原子、水酸基および シアン基から選択されたものが好 ましい。〕 即ち本発明においては、前記一般式(13または一般式
〔■′〕で示されるビスアゾ化合物をCGMとして用い
ると共に、一般式〔■〕で示されるスチリル化合物およ
び/または一般式[111)で示されるアミン訪導体な
C’l”Mとして用いてこれらを組合せることにより、
キャリアの発生と輸送とをそれぞれ別個の物質で行なう
いわゆる機能分離型感光体の感光層を構成する。そして
このことにより、感度が犬ぎく、しかも繰り返し電子写
真プロセスに供しく17) たときにも電位の履歴状態が安定に維持され従って常に
良知な可視画イ8jを形成し得る電子写真感光体を提供
することができる。
General formula [1b] N A-N=N-Ar 7-C11=C-Ar8-CI-1
= Ckl-A r 9-N=N -A [wherein, A is the same as the general formula I] or the general formula [I/], Ar7, ArB and M: substituted, unsubstituted It represents the phenyl group of the canter, and the animal-handling groups include alkyl threads such as methyl group and ethyl group, alkoxy groups such as methoxy group and ethoxy group, halogen atoms such as chlorine atom and bromine atom, hydroxyl group and cyan group. The selected one is preferred. ] That is, in the present invention, the bisazo compound represented by the general formula (13 or general formula [■']) is used as a CGM, and the styryl compound represented by the general formula [■] and/or the bisazo compound represented by the general formula [111] is used as a CGM. By combining these using C'l''M as an amine-conducting conductor,
It constitutes a photosensitive layer of a so-called functionally separated photoreceptor in which carrier generation and transport are performed using separate substances. This makes it possible to create an electrophotographic photoreceptor that maintains a stable potential history state even when subjected to repeated electrophotographic processes (17) and is therefore capable of always forming a well-defined visible image. can be provided.

また本元明?11子写真感光体においては、特に波長6
00〜700nmの長波Jく枕にも大きな分光感就が得
られ、仕って++:iえば波長6328Aのヘリウムー
ネオンレーツン沿f’l形成用光祿として用いることか
でき、史に低、に昼時におけるいわゆる電イ\シの裾切
れか良好でJ、i;l I)’47時(C非両終rol
lの電位が零またはこれ(τ近し・状態となるので、大
きな実効バイアスを得ることのできないトナーのみより
成る一成分釈(1:、:剤によっても良好7エ慴併を行
t−5ことができる。
Akira Motomoto again? In the 11-child photographic photoreceptor, especially wavelength 6
A large spectral sensitivity can be obtained even in the long wave wavelength range of 00 to 700 nm, and therefore it can be used as a light beam for forming helium-neon lasers with a wavelength of 6328 A, which is the lowest in history. , J,i;l I) '47 o'clock (C non-end rol
Since the potential of l is zero or close to this (τ), it is not possible to obtain a large effective bias.One-component solution consisting only of toner (1:,: also works well with agent) t-5 be able to.

前記一般式〔I〕で示されるビスアゾ化合物の具体例と
しては、1クリえば次の構造式を有するものを挙げるこ
とがCきるが、これらに限定されるものではない、1 例示化合物 V                  −ノ    
              〜ノ前記一般式〔1′〕
で示されるビスアゾ化合物の具体例としては、1タリえ
は次の構造式を有するものを茅げろことができるか、こ
れらに駆足されるものではない。
Specific examples of the bisazo compound represented by the general formula [I] include those having the following structural formula, but are not limited to these.1 Exemplary Compound V-No.
-The above general formula [1']
As a specific example of the bisazo compound represented by the formula, those having the following structural formulas may be used, but these compounds are not sufficient.

例示化合物 前記一般式〔11〕で示されるスチリル化合物の具1;
ト例としては、例えば次の構造式を有するものを挙げる
ことができるが、これらに限定されるものではない。
Exemplary compound Styryl compound represented by the general formula [11] 1;
Examples include, for example, those having the following structural formula, but are not limited thereto.

例示化置物 (n−]) (n−2) (11,−3) (II−4) (n−5) (It−6) (II−7) (II−8) (11−9) (IJ −10) (11−11) (II−12) (n−13) (u−14) (n−15) (II −16’) 3G (11−22) (1,1−23) (II−24) (11−25) (n−26) (1,t−27) (II−28) (L[−32) (II−33) (IF−34) 前記一般式(Ill)で示されるアミン誘導体の具体例
としては、例えば次の構造式を有するものを挙げること
ができるが、これらに限定されるものではない。
Illustrated figurine (n-]) (n-2) (11,-3) (II-4) (n-5) (It-6) (II-7) (II-8) (11-9) ( IJ -10) (11-11) (II-12) (n-13) (u-14) (n-15) (II -16') 3G (11-22) (1,1-23) (II -24) (11-25) (n-26) (1,t-27) (II-28) (L[-32) (II-33) (IF-34) Represented by the above general formula (Ill) Specific examples of amine derivatives include, but are not limited to, those having the following structural formula.

例示化合物 (In−1) (Ill−2) (III−3) (Ill−4) (111−り) (tu−6) (Ill−7) (nt−s) (■t−9) (nu−10) (III −11) (111−12) (III −13) (III−14) (Ill−15) (III−16) (III−17) (III−18) (III−19) (Hl−20) (Ill−21) (lll−22) (Ill−23) (ill−24) (III −25) (Ill−26) (III−27) (III−28) (■−29) (III−30) (III−31) (III−32) (III−33) 次に本発明電子写真感光体の機械的構成について説明す
る。
Exemplary compounds (In-1) (Ill-2) (III-3) (Ill-4) (111-ri) (tu-6) (Ill-7) (nt-s) (■t-9) (nu -10) (III-11) (111-12) (III-13) (III-14) (Ill-15) (III-16) (III-17) (III-18) (III-19) (Hl -20) (Ill-21) (llll-22) (Ill-23) (ill-24) (III -25) (Ill-26) (III-27) (III-28) (■-29) (III -30) (III-31) (III-32) (III-33) Next, the mechanical structure of the electrophotographic photoreceptor of the present invention will be explained.

本発明の一例においては、第1図に示すように、$1&
性支持体1上に既述のビスアゾ化合物を主成分として含
有して成るCGL2を形成し、このCGLZ上に既述の
スチリル化合物及び/又はアミン誘導体を主成分として
含有して成るC T L 3を積層して形成し、これら
のCGL2とCTL3とにより感光層4を構成する。
In one example of the present invention, as shown in FIG.
A CGL 2 containing the above-mentioned bisazo compound as a main component is formed on the sexual support 1, and a CTL 3 containing the above-mentioned styryl compound and/or amine derivative as a main component is formed on this CGLZ. These CGL2 and CTL3 constitute the photosensitive layer 4.

ここに前記導電性支持体1の材質としては、例えばアル
ミニウム、ニッケル、銅、亜鉛、パラジウム、銀、イン
ジウム、錫、白金、金、ステンレス鋼、真鍮等の金属の
シートを用℃・ることかできる、。
Here, as the material of the conductive support 1, for example, a sheet of metal such as aluminum, nickel, copper, zinc, palladium, silver, indium, tin, platinum, gold, stainless steel, or brass may be used. can,.

しかしこれらに限定されるものではなく、例えば第2図
に示すように、絶縁性基体IA上に導電層IBを設けて
導電性支持体1を構成せしめることもでき、この場合に
おいて基体IAとしては紙、プラスチックシー) %の
可捺性を有し、しかも曲げ、引張り等の応力に対して十
分な強度を有するものが適当である。又導電層IBは金
属シートをラミネートし或いは金属を真空蒸着せしめる
ことにより、又はその他の方法によって設けることがで
きる。
However, the invention is not limited thereto, and for example, as shown in FIG. 2, a conductive layer IB may be provided on an insulating base IA to constitute the conductive support 1. In this case, the base IA may be % of paper, plastic sheets) and has sufficient strength against stress such as bending and tension. The conductive layer IB can also be provided by laminating metal sheets, vacuum depositing metals, or by other methods.

前記CG L 2は、既述のビスアゾ化合物単独により
、又はこれに適当なバインダー樹脂を加えたものにより
、或いは更に特定又は非特定の極性のキャリアに対する
移動度の大きい物質即ちCTMを添加したものにより形
成することができる。
The above-mentioned CG L 2 is made of the above-mentioned bisazo compound alone, or added with a suitable binder resin, or further added with a substance having a high mobility for specific or non-specific polar carriers, that is, CTM. can be formed.

具体的な方法としては、前記支持体上に、既述のビスア
ゾ化合物を適当な溶剤に単独で或いは過当なバインダー
樹脂と共に溶解若しくは分散せしめたものを塗布して乾
燥せしめる方法が好便に利用される。
As a specific method, a method is conveniently used in which the above-described bisazo compound is dissolved or dispersed in an appropriate solvent or dissolved or dispersed together with an appropriate binder resin and then dried. Ru.

この方法にお(・て、溶媒或いは分散媒としては、例え
ばrl−ブチルアミン、ジエチルアミン、エチレンジア
ミン、インプロパツールアミン、モノエタノールアミン
、トリエタノールアミン、トリエチレンジアミン、N、
N−ジメチルホルムアミド、アセトン、メチルエチルケ
トン、シクロヘキサノン、ベンゼン、トルエン、キシレ
ン、クロロホルム、1.2−ジクロロエタン、ジクロロ
メタン、テトラヒドロフラン、ジオキサン、メタノール
、エタノール、インプロパノール、酢酸エチル、酢酸ブ
チル、ジメチルスルホキシド、その他を用いることがで
きる。
In this method, examples of the solvent or dispersion medium include RL-butylamine, diethylamine, ethylenediamine, improperamine, monoethanolamine, triethanolamine, triethylenediamine, N,
Using N-dimethylformamide, acetone, methyl ethyl ketone, cyclohexanone, benzene, toluene, xylene, chloroform, 1,2-dichloroethane, dichloromethane, tetrahydrofuran, dioxane, methanol, ethanol, impropanol, ethyl acetate, butyl acetate, dimethyl sulfoxide, etc. be able to.

また、バインダー樹脂としては、例えばポリエチレン、
ボリア0ロピレン、アクリル樹脂iT、 メタクリル樹
脂、塩化ビニル樹脂、酢酸ビニル樹脂、エポキシi鉦L
)l旨、ポリウレタン樹)Ih、フェノール廿1JI旨
、ポリエステル樹脂ぼ、アルキッド4III脂、ポリカ
ーボネート樹力汀、シリコン樹脂、メラミン樹脂I等の
付加重合型樹脂、重付加型a+脂、重縮合型(・71脂
、並びにこれらの樹脂の繰り返し単位のうちの2つ以上
を含む共重合体樹脂、例えば塩化ビニル−酢酸ビニル共
重合体樹脂、塩化ビニル−酢酸ビニル−無水マレイン酵
共重合体樹脂等の絶縁性桐朋の他、ポリ−N−ビニルカ
ルバゾール等の高分子有機半導体を芋げることかできる
。そして、このバインダー樹脂のビスアゾ化合物に対す
る割合は、0〜100重量係、特に0〜10重量%の範
囲である。
Further, as the binder resin, for example, polyethylene,
Boria 0 lopyrene, acrylic resin iT, methacrylic resin, vinyl chloride resin, vinyl acetate resin, epoxy i-ton L
) l, polyurethane resin) Ih, phenol 1JI, polyester resin, alkyd 4III resin, polycarbonate resin, silicone resin, melamine resin I, etc., addition polymerization type resin, polyaddition type a + resin, polycondensation type (・71 resin and copolymer resins containing two or more of the repeating units of these resins, such as vinyl chloride-vinyl acetate copolymer resin, vinyl chloride-vinyl acetate-maleic anhydride copolymer resin, etc. In addition to insulating paulownia, polymeric organic semiconductors such as poly-N-vinylcarbazole can also be used.The ratio of this binder resin to the bisazo compound is 0 to 100% by weight, particularly 0 to 10% by weight. is within the range of

前記CGL2には、必要に応じて適宜のCTMを添加し
てもよい。
An appropriate CTM may be added to the CGL2 as necessary.

以上のようにして形成される前記CGL2の厚さは、好
ましくは0.005〜20ミクロン、特に好ましくは0
.05〜5ミクロンである。0.005ミクロン未満で
は充分な光感度が得られず、また20ミクロンを越える
と充分な電荷保持性が得られない。
The thickness of the CGL 2 formed as described above is preferably 0.005 to 20 microns, particularly preferably 0.005 to 20 microns, particularly preferably 0.
.. 05-5 microns. If it is less than 0.005 microns, sufficient photosensitivity cannot be obtained, and if it exceeds 20 microns, sufficient charge retention cannot be obtained.

また前記CTL3は、既述のスチリル化合物及び/又は
アミン酵導体により、上述のCGL2と同様にして、即
ち単独で或いはバインダー樹脂と共に形成することがで
きる。そして、他のCTMを含有せしめてもよい。この
CTL3の崩さば2〜100ミクロン、好ましくは5〜
30ミクロンである。
Further, the CTL3 can be formed using the styryl compound and/or the amine enzyme conductor described above in the same manner as the CGL2 described above, that is, alone or together with a binder resin. Further, other CTMs may be included. The size of this CTL3 is 2 to 100 microns, preferably 5 to 100 microns.
It is 30 microns.

本発明電子写真感光体は、他の機械的構成とすることが
できる。例えば第3図に示すように、導電性支持体1上
に適当な中間層5を設け、これを介してCGL2を形成
し、このCGL2上にCTL3を形成するようにしても
よい。この中間層5には、感光層4の帯電時において導
電性支持体lから感光層4にフリーキャリアが注入され
ることを阻止する機能、或いは感光層4を導電性支持体
に対して−・体重に接着せしめる接着層としての機能を
有せしめることができる。斯かる中間層5の材質として
は、酸化アルミニウム、酸化インジウム等の金属酸化物
、アクリル樹脂、メタクリル初脂、塩化ビニル(υj&
、酢酸ビニル樹脂、エポキシ初詣、ポリウレタン樹月a
、フェノール4匍月ば、ポリエステル樹Jfti、アル
キッド樹脂、ポリカーボネート樹脂、シリコン樹脂、メ
ラミン初脂、塩化ビニル−酢酸ビニル共重合体樹脂、塩
化ビニル−酢酸ビニル−無水マレイン醒共垂合体(ii
l 脂等の筒分イ物質を用いることができる。
The electrophotographic photoreceptor of the present invention may have other mechanical configurations. For example, as shown in FIG. 3, a suitable intermediate layer 5 may be provided on the conductive support 1, a CGL 2 may be formed through this, and a CTL 3 may be formed on this CGL 2. This intermediate layer 5 has a function of preventing free carriers from being injected into the photosensitive layer 4 from the conductive support l when the photosensitive layer 4 is charged, or a function of preventing the photosensitive layer 4 from being injected into the photosensitive layer 4 from the conductive support. It can function as an adhesive layer that adheres to body weight. Materials for the intermediate layer 5 include metal oxides such as aluminum oxide and indium oxide, acrylic resin, methacrylic resin, and vinyl chloride (υj&
, vinyl acetate resin, epoxy hatsumode, polyurethane juzuki a
, phenol 4-ring moon, polyester resin Jfti, alkyd resin, polycarbonate resin, silicone resin, melamine fat, vinyl chloride-vinyl acetate copolymer resin, vinyl chloride-vinyl acetate-maleic anhydride copolymer (II)
A material such as fat can be used.

又第4図に示すように、尋電性支持坏1上に、前記中間
層5を介して又は介さずに、C’i” L 3を形成し
、このCT L 3上にCGL2を形成して感光層4を
構成せしめてもよい。
Further, as shown in FIG. 4, C'i'' L 3 is formed on the conductive support 1 with or without the intermediate layer 5, and CGL 2 is formed on this CT L 3. The photosensitive layer 4 may also be constructed using the following methods.

史に、ル”L述のビスアゾ化合物を、既述のスチリル化
合物及び/又はアミン誘導体が自櫓されたキャリア輸送
相中に分散含有せしめ・てキャリア発生相な形成し、単
一層状の感光j−を形成することも可能である。
In history, the bisazo compound described above was dispersed in a carrier transport phase in which the styryl compound and/or amine derivative described above were self-contained to form a carrier generation phase, and a single layer of photosensitive material was obtained. It is also possible to form -.

なお、本発明における感光層を構成する層には、必要に
応じて柚々の添刀口剤を加えることができる。
Incidentally, a citron additive may be added to the layer constituting the photosensitive layer in the present invention, if necessary.

以下本発明の実施例について説明するが、これらによっ
て本発明が限定されるものではない。
Examples of the present invention will be described below, but the present invention is not limited thereto.

実施例1 アルミニウムを蒸着した厚さ100ミクロンのポリエチ
レンテレフタレートより成る導電性支持体上に、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(種水化学工業社製)より成る厚さ約
0.05ミクロンの中間層を設け、例示化合物(1−9
)で示したビスアゾ化合物1.5Iを1,2−ジクロル
エタン100+nJと共に8時間ボールミルにより分散
し、ここに得られた分散液を前記中間層上にドクターブ
レードを用いて塗布し、十分乾燥して片さio、5ミク
ロンのCGI、を形成し を二。
Example 1 A vinyl chloride-vinyl acetate-maleic anhydride copolymer [from S-LEC MF' = 10J (manufactured by Tanezu Chemical Industry Co., Ltd.) An intermediate layer having a thickness of about 0.05 microns is provided, and the exemplified compound (1-9
) was dispersed with 100+ nJ of 1,2-dichloroethane in a ball mill for 8 hours, and the resulting dispersion was applied onto the intermediate layer using a doctor blade, dried thoroughly, and peeled. io, 5 micron CGI, form the second.

一方、例示化合物(II−22)で示したスチリル化合
物11.25.9とポリカーボネート樹脂1パンライト
L−1250J(怜大化成社製)15gとを1,2一ジ
クロノtエタン100m1に溶解し、得られた溶液を前
記CG I−上にドクターブレードを用いて塗布し、十
分乾燥12て1ワ、さ12ミクロンのCT Lを形成し
、以って本発明電子写真感光体を製造した。これを1試
料1」とする。
On the other hand, styryl compound 11.25.9 shown as exemplified compound (II-22) and 15 g of polycarbonate resin 1 Panlite L-1250J (manufactured by Reidai Kasei Co., Ltd.) were dissolved in 100 ml of 1,2-dichlorot-ethane, The obtained solution was applied onto the CG I- using a doctor blade and thoroughly dried to form a CTL of 12 mm and 12 microns, thereby producing an electrophotographic photoreceptor of the present invention. This is referred to as 1 sample 1.

実7111例2〜8 CGLの形成及びCT Lの形成において、例示化合物
として下記第1表に示す組合せのものを用いた他は実施
例1と同様にして7種の本発明電子写真感光体を製造し
た。これらをそれぞれ1試料2」〜「試料8」とする。
Example 7111 Examples 2 to 8 Seven types of electrophotographic photoreceptors of the present invention were prepared in the same manner as in Example 1, except that in the formation of CGL and CTL, the combinations shown in Table 1 below were used as exemplary compounds. Manufactured. These will be referred to as 1 sample 2'' to 1 sample 8, respectively.

第1表 実施例9 実施例1におけると同様にして導電性支持体上に中間層
を設け、例示化合物(1−9)で示したビスアゾ化合物
の1.5gとポリカーボネート樹脂[パソライトl、−
1250Jの159とを1,2−ジクロルエタン100
mJに加えて12時間ボールミルによりドクターブレー
ドにより塗布し、十分乾燥させて厚さ約1ミクロンのC
GLを形成した。
Table 1 Example 9 An intermediate layer was provided on a conductive support in the same manner as in Example 1, and 1.5 g of the bisazo compound shown as exemplified compound (1-9) and a polycarbonate resin [Pasolite l, -
159 of 1250J and 100 of 1,2-dichloroethane
In addition to mJ, apply with a doctor blade using a ball mill for 12 hours, and dry thoroughly to form a C of approximately 1 micron in thickness.
GL was formed.

このCGL上に、実施例1におけると同様にしてCTL
を形成し、以って本発明電子写真感光体を製造した。こ
れを「試料9」とする。
On this CGL, CTL was added in the same manner as in Example 1.
was formed, thereby producing an electrophotographic photoreceptor of the present invention. This will be referred to as "Sample 9."

実施例10 CGLの形成において、ビスアゾ化合物として例示化合
物(+’−43)で示したものを用い、CTLの形成に
おいて、スチリル化合物として例示化合物(n−33)
で示したものを用いたほかは実施例9と全く同様にして
本発明電子写真感光体を製造した。これを1試料10」
とする。
Example 10 In the formation of CGL, the exemplified compound (+'-43) was used as the bisazo compound, and in the formation of CTL, the exemplified compound (n-33) was used as the styryl compound.
An electrophotographic photoreceptor of the present invention was produced in exactly the same manner as in Example 9 except that the material shown in . 1 sample of this 10"
shall be.

比較例1 実施例1のCTLの形成において、スチリル化合物の代
りに次の構造式を有するピラゾリン811体を用いたほ
かは、実施例1と同様にして比較用電子写真感光体を製
造した。これを「比較試料l」とする。
Comparative Example 1 A comparative electrophotographic photoreceptor was produced in the same manner as in Example 1, except that pyrazoline 811 having the following structural formula was used instead of the styryl compound in the formation of CTL in Example 1. This will be referred to as "comparative sample 1."

比較例2 実施例1のCTLの形成において、スチリル化合物の代
りに次の構造式を有するオキサジアゾール誘導体を用い
たほかは、実施例1と同様にして比較用電子写真感光体
を製造した。これを1比較試料2」とする。
Comparative Example 2 A comparative electrophotographic photoreceptor was produced in the same manner as in Example 1, except that an oxadiazole derivative having the following structural formula was used in place of the styryl compound in forming the CTL in Example 1. This will be referred to as 1 Comparative Sample 2.

以上のようにして得られた電子写真感光体、試料1〜試
料10並びに比較試料1及び比較試料2の各々について
、「エレクトロメーター5P−428型」(川口電機製
作精製)を用いて、その電子写真特性を調べた。即ち感
光体表面を帯電電圧−6KVで5秒間帯電させた時の受
容電位■A(V)と、5秒間暗減衰させた後の電位VI
(初期電位)をIAに減哀させるために必要な露光量E
 1/2 (1uxa秒)、更に8)f減衰率(VA−
Vl)/VAX100(%)とを調べた。
The electrophotographic photoreceptors obtained as described above, Samples 1 to 10, Comparative Sample 1, and Comparative Sample 2 were each tested using an "Electrometer Model 5P-428" (manufactured by Kawaguchi Denki). The photographic characteristics were investigated. That is, the acceptance potential ■A (V) when the photoreceptor surface is charged for 5 seconds at a charging voltage of -6 KV, and the potential VI after dark decay for 5 seconds.
Exposure amount E required to reduce (initial potential) to IA
1/2 (1uxa seconds), further 8) f decay rate (VA-
Vl)/VAX100 (%).

結果は第2表に示す通りでJSる。The results are shown in Table 2.

第  2  表 この第2表の結果より、本発明電子写真感光体は大きな
感度を肩するものであることが明かである。
Table 2 From the results in Table 2, it is clear that the electrophotographic photoreceptor of the present invention has a high sensitivity.

また試料1〜試料1o並びに比較試料1と比較試料2の
各々を乾式′電子複写11.4 I−U −B i x
 2000Rj(小西六写真工業社製)に装着して連続
複写を行ない、露光絞り値1.0における黒紙電位vb
(v)及び白紙電位Vw(V)を「エレクトロスタチッ
クボルトメーター1441)−1D型」 (モンローエ
レクトロニクスインコーポレーテッド製)を用い、現像
する直前において画定した。結果は第3表に示す通りで
ある。
In addition, each of Samples 1 to 1o and Comparative Sample 1 and Comparative Sample 2 was dry-electronically copied 11.4 I-U-B i x
2000Rj (manufactured by Konishiroku Photo Industry Co., Ltd.) for continuous copying, and the black paper potential vb at an exposure aperture value of 1.0.
(v) and white paper potential Vw (V) were determined using an "Electrostatic Voltmeter 1441)-1D Model" (manufactured by Monroe Electronics, Inc.) immediately before development. The results are shown in Table 3.

向ここでいう黒紙電位とは反射濃度1.3の黒紙を原稿
とし、上述の複写サイクルを実施したときの感光体の表
面電位を表わし、白紙電位とは白紙を原稿としたときの
感光体の表面電位を表わす。
The black paper potential here refers to the surface potential of the photoreceptor when the above-mentioned copying cycle is performed using a black paper with a reflection density of 1.3 as the original, and the white paper potential refers to the surface potential of the photoreceptor when the original is a black paper with a reflection density of 1.3. Represents the surface potential of the body.

第3表 (但し、表中△vb(v)及び△Vw(V)はそれぞれ
黒紙電位vb(v)及び白紙電位VW(V)の変動量を
示し、変動量の+は増加を−は減少を懺わす。) この第3表の結果から明かなように、本発明電子写真感
光体は、繰り返し電子写真プロセスに供したときにも電
位の履歴状態が安定に維持され、良好な画質の可視画像
を多数安定に形成することができる。
Table 3 (However, △vb (v) and △Vw (V) in the table indicate the amount of variation in the black paper potential vb (v) and white paper potential VW (V), respectively, and + in the variation amount indicates an increase As is clear from the results in Table 3, the electrophotographic photoreceptor of the present invention maintains the potential history state stably even when subjected to repeated electrophotographic processes, resulting in good image quality. A large number of visible images can be stably formed.

【図面の簡単な説明】[Brief explanation of the drawing]

第1図は本発明電子写真感光体の構成の一例を示す説、
明月断面図、第2図は本発明電子写真感光体の他の構成
例を示す説明用断面図、第3図及び第4図はそれぞれ本
発明電子写真感光体の更に他の構成例を示す説明用断面
図である。 ■ ・・・ 導゛亀性支持体 2 ・・・ キャリア発生層(CGL)3 ・・・ キ
ャリア輸送II(CTL)4 ・・・ 感光層  5 
・・・ 中間層IA・・・ 絶縁性基体 lB・・・ 
専電層図面のr」°[店(内′;イに変更なし)差 l
囮 第2図 学3図 乍4図 手続補正書、ヵ、、:) 昭和58年4月2G日 特許庁長官 若杉和夫 殿 l 事件の表示 昭和 57年    特許願第214034号2 発明
の名称   電子写真感光体 3、補正をする者 事件との関係  特許出願人 6−リガ、;、   東京都新宿区西新宿1丁目26@
2号罠v11銘称) (127)小西六写真工業株式会
社4、代理人 5 補正命令の日付  昭和58年3月29日6 補正
により増加する発明の数 2)図面の浄書(内容に変更なし)
FIG. 1 shows an example of the structure of the electrophotographic photoreceptor of the present invention.
2 is an explanatory sectional view showing another example of the electrophotographic photoreceptor of the present invention, and FIGS. 3 and 4 are explanatory sectional views showing still other examples of the electrophotographic photoreceptor of the invention, respectively. FIG. ■ ... Transmissive support 2 ... Carrier generation layer (CGL) 3 ... Carrier transport II (CTL) 4 ... Photosensitive layer 5
... Intermediate layer IA... Insulating base IB...
R'' ° [store (inside'; no change in A) difference l of exclusive electric layer drawing
Decoy Figure 2, Figures 3 and 4, Procedural Amendments, Ka,,:) April 2, 1982 Commissioner of the Patent Office Kazuo Wakasugi Representation of the case 1982 Patent Application No. 214034 2 Title of the invention Electronic photography Photoconductor 3, relationship with the amended person case Patent applicant 6 - Riga; 1-26 Nishi-Shinjuku, Shinjuku-ku, Tokyo @
No. 2 Trap v11 name) (127) Roku Konishi Photo Industry Co., Ltd. 4, Agent 5 Date of amendment order March 29, 1981 6 Number of inventions increased by amendment 2) Engraving of drawings (no change in content) )

Claims (1)

【特許請求の範囲】 1)キャリア発生相とキャリア輸送相とを組合せて成る
感光層を導電性支持体上に設けて成る電子写真感光体に
おいて、前記キャリア発生相が下記一般式CI)または
一般式〔lI〕で示されるビスアゾ化合物を含有し、前
記キャリア輸送和か下記一般式〔■〕で示されるスチリ
ル化合物及び下記一般式[III 〕で示されるアミン
誘導体の少なくとも一方を含有することを特徴とする電
子写真感光体。 一般式〔I〕 1(1 A−N=N−Ar1−C1−1=c−Ar2−CH,=
Cl−1−Ar3−N=N−A一般式〔I“〕 A N=IN−ArI C11=CAr2 C=CH−
Ar3 N=N −A〔式中、 A r 1・Ar2オヨヒAr3 :それぞれ置換、未
置換の炭素環式芳香族環基、 Hlまたはl(2:それぞれ電子吸引性基、A ニ ーNH302((6、 Y:水素原子、ノ・ロゲン原子、置 換、未置換のアルキル基、ア ルコキシ基、カルボキシル基、 スルホ基、置換、未置換のカ ルバモイル基または置換、未 置換のスルファモイル基、 (但し、Il+が2以上のときは、 互に異なる基であってもよい。) Z:置換、未16換の炭素環式芳香 族環または置換、未置換の複 素環式芳香族環を構成するに 必要な原子群、 R96:水素原子、置換、未置換のア ミン基、置換、未置換のカル バモイル基、カルボキシル基 またはそのエステル基、 A1:置換、未1d換のアリール基、 n:1または2の整数、 m:0〜4の整数を表わす。〕 一般式[111) %式% 〔式中l(,7J(8:置換、未置換のアルキル基、フ
ェニル基を表わし、置換基としては アルキル基、アルコキシ基、フェ ニル基を用いる。 R9: 置換、未置換のフェニル基、ナフチル基、アン
トリル基、フルオレ ニル基または複素環基を表わし、 置抄基としてはアルキル基、アル コキシ基、ハロゲン原子、水酸基、 フェニル基を用いる。 R10”””’1+:水素原子、ハロゲン原子、アルキ
ル基、7/l/コキシ基またはアルキ ルアミノ基を表わす。〕 一般式Cm) Ar4 \ N −−Ar 6 / Ar5 〔式中Ar4、Ar5:置換、未置換のフェニル基を表
わし、置換基としてはハロゲン原子X子、アルキル基、
ニトロ基、アルコキ シ基を用(・る。 Ar6:置換、未置換のフェニル基、ナフチル基、アン
トリル基、フルオレ ニル基、複素環基を表わし、置換 基としてはアルキル基、アルコキ シ基、ハロゲン原子、水酸基、ア リールメキシ基、アリール基、ア ミン基、ニトロ基、ヒペリジノ基、 モルホリノ基、ナフチル基、アン スリル基及び置換アミン基を用い る。但し、置換アミノ基の置換基 としとアシル基、アルキル基、ア リール基、アラルキル基を用いる0〕
[Scope of Claims] 1) An electrophotographic photoreceptor comprising a photosensitive layer comprising a combination of a carrier generation phase and a carrier transport phase provided on a conductive support, wherein the carrier generation phase is formed by the following general formula CI) or the general formula It is characterized by containing a bisazo compound represented by the formula [lI], and at least one of the carrier transport compound, a styryl compound represented by the following general formula [■], and an amine derivative represented by the following general formula [III]. An electrophotographic photoreceptor. General formula [I] 1(1 A-N=N-Ar1-C1-1=c-Ar2-CH,=
Cl-1-Ar3-N=NA general formula [I"] A N=IN-ArI C11=CAR2 C=CH-
Ar3 N=N-A [wherein, Ar3: each substituted or unsubstituted carbocyclic aromatic ring group, Hl or l (2: each electron-withdrawing group, A niNH302 ((6 , Y: hydrogen atom, hydrogen atom, substituted or unsubstituted alkyl group, alkoxy group, carboxyl group, sulfo group, substituted or unsubstituted carbamoyl group, or substituted or unsubstituted sulfamoyl group, (provided that Il+ is 2 In the above cases, groups may be different from each other.) Z: Atom group necessary to constitute a substituted or un16-substituted carbocyclic aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring. , R96: hydrogen atom, substituted or unsubstituted amine group, substituted or unsubstituted carbamoyl group, carboxyl group or ester group thereof, A1: substituted or unsubstituted aryl group, n: integer of 1 or 2, m: Represents an integer from 0 to 4.] General formula [111) %Formula% [In the formula, l(, 7J (8: represents a substituted or unsubstituted alkyl group, phenyl group, and substituents include an alkyl group, an alkoxy group, A phenyl group is used. R9: Represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group, fluorenyl group, or heterocyclic group, and as a substituted group, an alkyl group, an alkoxy group, a halogen atom, a hydroxyl group, or a phenyl group is used. R10"""'1+: represents a hydrogen atom, a halogen atom, an alkyl group, a 7/l/koxy group, or an alkylamino group.] General formula Cm) Ar4\N --Ar6/Ar5 [In the formula, Ar4, Ar5 : Represents a substituted or unsubstituted phenyl group, and substituents include a halogen atom, an alkyl group,
A nitro group or an alkoxy group is used (・Ar6: represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group, fluorenyl group, or heterocyclic group; substituents include an alkyl group, an alkoxy group, a halogen atom, or a hydroxyl group) , arylmexy group, aryl group, amine group, nitro group, hyperidino group, morpholino group, naphthyl group, anthryl group, and substituted amine group.However, as a substituent for the substituted amino group, acyl group, alkyl group, and aryl group are used. ,0 using an aralkyl group]
JP57214034A 1982-11-10 1982-12-08 Electrophotographic sensitive body Granted JPS59104653A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP57214034A JPS59104653A (en) 1982-12-08 1982-12-08 Electrophotographic sensitive body
US06/549,601 US4540651A (en) 1982-11-10 1983-11-07 Electrophotographic photosensitive member

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP57214034A JPS59104653A (en) 1982-12-08 1982-12-08 Electrophotographic sensitive body

Publications (2)

Publication Number Publication Date
JPS59104653A true JPS59104653A (en) 1984-06-16
JPH0120421B2 JPH0120421B2 (en) 1989-04-17

Family

ID=16649177

Family Applications (1)

Application Number Title Priority Date Filing Date
JP57214034A Granted JPS59104653A (en) 1982-11-10 1982-12-08 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPS59104653A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0437310A2 (en) * 1990-01-08 1991-07-17 Hitachi, Ltd. Photosensitive element for electrophotography

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0437310A2 (en) * 1990-01-08 1991-07-17 Hitachi, Ltd. Photosensitive element for electrophotography

Also Published As

Publication number Publication date
JPH0120421B2 (en) 1989-04-17

Similar Documents

Publication Publication Date Title
JP2917426B2 (en) Photoconductor
JPS59104653A (en) Electrophotographic sensitive body
JPH037945A (en) Electrophotographic sensitive body
JPH08320581A (en) Electrophotographic photoreceptor
JPH0146066B2 (en)
JPH0118415B2 (en)
JPH0120419B2 (en)
JPH0118419B2 (en)
JPH0118421B2 (en)
JPH0118417B2 (en)
JPH0325773B2 (en)
JPH0118418B2 (en)
JPH0325776B2 (en)
JPH0120422B2 (en)
JPS59104657A (en) Electrophotographic sensitive body
JPH0118416B2 (en)
JPS59104655A (en) Electrophotographic sensitive body
JPH0146065B2 (en)
JPS61284769A (en) Electrophotographic sensitive body
JPH0146064B2 (en)
JPH0120420B2 (en)
JPH0118420B2 (en)
JPH0146062B2 (en)
JPS5999444A (en) Electrophotographic sensitive body
JPH0314173B2 (en)