JPS62121459A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPS62121459A
JPS62121459A JP25978485A JP25978485A JPS62121459A JP S62121459 A JPS62121459 A JP S62121459A JP 25978485 A JP25978485 A JP 25978485A JP 25978485 A JP25978485 A JP 25978485A JP S62121459 A JPS62121459 A JP S62121459A
Authority
JP
Japan
Prior art keywords
alkyl
electric charge
formula
group
aryl
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
JP25978485A
Other languages
Japanese (ja)
Inventor
Masashi Kumagai
正志 熊谷
Toru Imori
徹 伊森
Toshihiro Hirai
平井 利弘
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.)
Eneos Corp
Original Assignee
Nippon Mining Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Mining Co Ltd filed Critical Nippon Mining Co Ltd
Priority to JP25978485A priority Critical patent/JPS62121459A/en
Publication of JPS62121459A publication Critical patent/JPS62121459A/en
Pending 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
    • G03G5/0601Acyclic 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
    • G03G5/0627Heterocyclic compounds containing one hetero ring being five-membered
    • G03G5/0631Heterocyclic compounds containing one hetero ring being five-membered containing two hetero atoms
    • 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

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

PURPOSE:To obtain the titled body capable of holding a high photosensitive characteristics and having improved electric charge fatigue and electrostatic properties by jointly using specific kinds of the electric charge transfer agents in a prescribed ratio. CONSTITUTION:A beta type copper phthalocyanine is used as the electric charge generating agent. The electric charge carrier layer comprises 0.8-5.0pts.wt. a compd. shown by formula (II) on the basis of 100pts.wt. a compd. shown by formula (I) as a main component. In formula I, R1 is 2-4C an alkyl group, R2 is an aryl or an alkyl substd. aryl group. In formula II, R1 is 2-4C an alkyl group, R2 is 2-4C an alkyl or an aryl or an alkyl substd. aryl group, R3 is an aryl or a benzyl group. Said two compds. are mixed with a small amount of a binding agent such as a polycarbonate resin etc., and chloroform to prepare a coating solution. The obtd. coating solution is coated on the surface of the electric charge generating layer, and dried to form the electric charge transfer layer.

Description

【発明の詳細な説明】 技術分野 本発明は電荷発生層と電荷搬送層を導電性支持体に積層
して成る電子写真用感光体に関する。
DETAILED DESCRIPTION OF THE INVENTION Technical Field The present invention relates to an electrophotographic photoreceptor comprising a charge generation layer and a charge transport layer laminated on a conductive support.

従来技術 フタロシアニン系化合物を電荷発生剤(以下CGMとい
う)とした電子写真用感光体は、普通紙複写機(ppc
)の感光体とし実用化が進んでいる。又レーザープリン
タ用としての用途も有望である。CGMは結着性樹脂に
分散し、導電性支持体表面に塗工し、電荷発生層(以下
CGLという)を形成する。光感度等の機能向上のため
、CGLの上に、電荷搬送剤(以下CTMという)を樹
脂で結着して成る電荷搬送層(以下(!TL)を形成し
た機能分担型積序型電子写真用感光体(以下単に感光体
という)が発表されている。
Prior Art Electrophotographic photoreceptors using phthalocyanine compounds as charge generating agents (hereinafter referred to as CGM) are used in plain paper copying machines (PPC).
) is being put into practical use as a photoreceptor. It is also promising for use in laser printers. CGM is dispersed in a binding resin and coated on the surface of a conductive support to form a charge generation layer (hereinafter referred to as CGL). In order to improve functions such as photosensitivity, a charge transport layer (hereinafter referred to as (!TL)) is formed on CGL by binding a charge transport agent (hereinafter referred to as CTM) with resin. A photoconductor (hereinafter simply referred to as a photoconductor) for use in photoconductors has been announced.

銀フタロシアニンをCGMとした感光体におけるCTM
として、多種が公知である。
CTM in photoreceptor using silver phthalocyanine as CGM
Many types are known as.

造が、特開昭60−24553.同58−199353
号公報に開示されており、又。
Built in Japanese Patent Publication No. 60-24553. 58-199353
It is disclosed in the publication No.

が、特開昭57−79981.同57−14844号公
報に開示されている。
However, JP-A-57-79981. It is disclosed in Japanese Patent Publication No. 57-14844.

しかしながら、各々単独で使用すると光感度は優れるも
のの、繰り返し使用による電荷疲労が大きく、あるいは
電荷疲労は良好であるが。
However, when each is used alone, although the photosensitivity is excellent, the charge fatigue due to repeated use is large, or the charge fatigue is good.

帯電性や光疲労が劣るという欠点がある。感光体として
の要求性能として、初期受容電位(Vo)が十分高く、
暗減衰率(D、D、R)が小さく、残留電位(V、)が
小さく、半減露光量(Ill)が小さく、さらには繰り
返し使用時の耐久性として。
It has disadvantages of poor charging properties and light fatigue. The required performance as a photoreceptor is that the initial acceptance potential (Vo) is sufficiently high;
Low dark decay rate (D, D, R), low residual potential (V,), low half-life exposure (Ill), and durability during repeated use.

上記初期特性を持続することが必要である。It is necessary to maintain the above initial characteristics.

これら諸特性を総合具備する感光体は、 CGMとCT
Lの選択・組合せで大きく左右される。
Photoreceptors that have all of these characteristics are CGM and CT.
It is greatly influenced by the selection and combination of L.

本発明が解決しようとする課題 本発明者は、β型鋼フタロシアニンをCGMとした感光
体の諸特性の一層の向上を計る目的で研究を進めたとこ
ろ、特定の異種のCTMを特定範囲で組み合せ使用する
ことにより、相乗的に諸特性が向上できることを見出し
た。
Problems to be Solved by the Present Invention The present inventor conducted research with the aim of further improving the various characteristics of a photoreceptor using β-type steel phthalocyanine as CGM, and found that a combination of specific different types of CTM was used within a specific range. It has been found that by doing so, various properties can be synergistically improved.

発明の構成 本発明の積層型電子写真用感光体は、電荷発生剤として
、β型銅フタロシアニンを使用したものであって、電荷
搬送層を構成する主成分が。
Structure of the Invention The laminated electrophotographic photoreceptor of the present invention uses β-type copper phthalocyanine as a charge generating agent, and the main component constituting the charge transport layer is β-type copper phthalocyanine.

以下の一般式(+)で示される化合物100重量部当り
、一般式([I)で表わされる化合物0.8〜5,0重
量部配合して成ることを特徴とするものである。
It is characterized in that 0.8 to 5.0 parts by weight of the compound represented by the general formula (I) is blended per 100 parts by weight of the compound represented by the following general formula (+).

一般式(1) 一般式(II) 以下より詳しく説明する。以下の説明において、上記一
般式(+)の化合物を総称してAPH2と略記し、又一
般式(II)の化合物を総称してPSPZと略記する。
General formula (1) General formula (II) This will be explained in more detail below. In the following description, the compounds of the general formula (+) are collectively abbreviated as APH2, and the compounds of the general formula (II) are collectively abbreviated as PSPZ.

本発明の感光体は、導電性支持体表面に、β型部フタロ
シアニンの超微粒子を結着性樹脂に分散したものを、薄
く均一に塗付してcGLを形成し、更にこのCGL上に
以下に記すCTLを形成したものである。
In the photoreceptor of the present invention, a cGL is formed by thinly and uniformly applying ultrafine particles of β-type moiety phthalocyanine dispersed in a binder resin to the surface of a conductive support, and then the following is applied on the CGL. The CTL shown in FIG.

導電性支持体として一般に知られているガラス、高分子
フィルムにアルミ蒸着又はアルミ箔接着したもの、ある
いはアルミ板自身を支持体とするもの等が例示される。
Examples of the conductive support include glass, a polymer film on which aluminum is vapor-deposited or aluminum foil is adhered, and an aluminum plate itself as a support.

β型鋼フタロシアニンは純度95%以上で。Beta type steel phthalocyanine has a purity of 95% or more.

平均粒径0.1μm以下、好ましくは0.05μm以下
のものである。β型銅フタロシアニンはX線回折で69
0 、 730 、 780 cm−’に回折パターン
を有する。結晶性樹脂として飽和、ポリエステル樹脂等
を用い、溶剤と共に混練し、前記支持体表面に01〜1
μm厚さで塗膜層をつくりCGLをつくる。
The average particle size is 0.1 μm or less, preferably 0.05 μm or less. β-type copper phthalocyanine is 69 by X-ray diffraction.
It has a diffraction pattern at 0, 730, and 780 cm-'. A saturated polyester resin or the like is used as the crystalline resin, kneaded with a solvent, and coated with 01 to 1 on the surface of the support.
Create a coating layer with a thickness of μm to create CGL.

本発明ではCTMとしそ、2種の異なる構造の化合物即
ちAPH2とpspzを100:0.8〜5.0の割合
で混合した混合体を使用する。
In the present invention, a mixture of CTM, shiso, and two types of compounds with different structures, namely APH2 and pspz, is used in a ratio of 100:0.8 to 5.0.

該割合は、諸特性の総合向上の見地にもとづき決定され
た。E’&特性としてAPH2はPSPZに比べ良好で
あるが1両者混合によシ相乗的に性能低下を来す領域が
あす、■R特性はPSPZがAPHzより優れるものの
2両者混合により同様相乗的に性能低下を来す領域が存
在する。
The ratio was determined based on the viewpoint of comprehensive improvement of various properties. As for E'& characteristics, APH2 is better than PSPZ, but there is a region where the performance deteriorates synergistically when both are mixed.■R characteristics are that PSPZ is better than APHz, but when both are mixed, the performance is synergistically lower. There are areas where performance deteriorates.

vO特性は適切な混合により相乗的に性能向上をもたら
す。とくに好ましいAPHzとPEIPZの割合は10
0 : 1.5〜3゜0(重量部)である。
VO properties synergistically improve performance through proper mixing. A particularly preferable ratio of APHz and PEIPZ is 10
0: 1.5 to 3°0 (parts by weight).

該両側は、ポリカーボネート樹脂等の結着剤とクロロホ
ルムを少量混合し、塗工液とし、前記CGL表面に膜厚
10〜30μm程度塗布し。
For both sides, a small amount of a binder such as a polycarbonate resin and chloroform are mixed to form a coating solution, and the coating solution is applied to the CGL surface to a thickness of about 10 to 30 μm.

乾燥し、OTLとする。Dry and use as OTL.

以下実施例にもとづき、効果等を説明する。Effects and the like will be explained below based on Examples.

実施例 β型銅フタロシアニン30重量部に対し、飽和ポリエス
テル樹脂(東洋紡紡績社製バイロン200)9重量部を
加え、液濃度がZ77重量部なるようにテトラヒドロフ
ランを加えて、樹脂を溶解しペイントコンディショナー
によシ1時間混練して電荷発生物質塗液を得た。この塗
液を膜厚約100μmのアルミニウムを蒸着したポリエ
チレンテレフタレートフィルムの上にワイヤーバーで乾
燥後の膜厚が0.1μmになるように塗布し、乾燥した
Example 9 parts by weight of a saturated polyester resin (Vylon 200 manufactured by Toyobo Co., Ltd.) was added to 30 parts by weight of β-type copper phthalocyanine, and tetrahydrofuran was added so that the liquid concentration was Z77 parts by weight to dissolve the resin and make a paint conditioner. The mixture was kneaded for 1 hour to obtain a charge generating substance coating liquid. This coating liquid was applied with a wire bar onto a polyethylene terephthalate film on which aluminum was deposited to a thickness of about 100 μm so that the film thickness after drying would be 0.1 μm, and then dried.

次いでp−ジエチルアミノベンズアルデヒド−ジフェニ
ルヒドラゾン(APH2)、!: 1−フェニル−5−
(p−ジエチルアミノスチリル)−5−(p−ジエチル
アミノフェニル)−ピラゾリン(pspz )をそれぞ
れ単独で2.02及び両者割合を変化させ1合計量を2
.0?としたCTMをポリカーボネート樹脂2g及びク
ロロホルム12−と混ぜ、CTL塗工液とした。
Then p-diethylaminobenzaldehyde-diphenylhydrazone (APH2),! : 1-phenyl-5-
(p-diethylaminostyryl)-5-(p-diethylaminophenyl)-pyrazoline (pspz) was used alone at 2.02, and by varying the ratio of both, the total amount of 1 was reduced to 2.02.
.. 0? The resulting CTM was mixed with 2 g of polycarbonate resin and 12-chloroform to prepare a CTL coating liquid.

各々の塗工液を先に作成した電荷発生層上にドクターブ
レードにより乾燥後の膜厚が約20μmとなるように塗
布し、乾燥した。
Each coating solution was applied onto the previously prepared charge generation layer using a doctor blade so that the film thickness after drying would be about 20 μm, and then dried.

このようにして作成した8種類の電子写真用感光体を川
口電機■製5P428型静電試験機を用いてスタチック
方式でコロナ放電電圧−5詩で帯電し、暗所で5秒間保
持した後、照度10 luxで露光し静電特性を調べた
The 8 types of electrophotographic photoreceptors created in this way were statically charged at a corona discharge voltage of -5 volts using a 5P428 electrostatic tester manufactured by Kawaguchi Electric, and after being held in a dark place for 5 seconds, It was exposed to light at an illuminance of 10 lux and its electrostatic properties were examined.

静電特性としては、初期電位をVo(ボルト)。As for electrostatic characteristics, the initial potential is Vo (volt).

暗所での5秒間の電位の減衰率をり、D、R、半減露光
量を8%4(lux−sea ) 、光照射10秒後に
残留する電位をVR(ボルト)として評価した。結果を
表に示す。
The attenuation rate of the potential for 5 seconds in the dark was evaluated as D, R, the half-decreased exposure amount as 8%4 (lux-sea), and the potential remaining after 10 seconds of light irradiation as VR (volt). The results are shown in the table.

表 又2表に示した感光体A、D及びEを用いて行った10
00回の繰り返し試験による残留電位vRの推移を図に
示した。
10 conducted using photoreceptors A, D and E shown in Table 2.
The graph shows the change in residual potential vR after 00 repeated tests.

図から明らかなように9本発明の感光体り及びEば10
00回の繰り返し使用においても。
As is clear from the figure, the photoreceptor 9 of the present invention and E10
Even after repeated use 00 times.

残留電位の変化をほとんど起さず、耐久性に優れる。Has excellent durability with almost no change in residual potential.

本発明の効果 本発明は、一般式(1)の化合物のCTMとしての高い
光感度特性を保持もしくは更に向上し。
Effects of the present invention The present invention maintains or further improves the high photosensitivity characteristics of the compound of general formula (1) as a CTM.

更に欠点である電荷疲労特性を改良し、更に静電特性も
向上した電子写真用感光体が得られた。
Furthermore, an electrophotographic photoreceptor was obtained in which the disadvantageous charge fatigue characteristics were improved and the electrostatic characteristics were further improved.

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

り醪 51子写真用感光体の゛繰り返し試験における残留電位
の推移を示したものである。
This figure shows the change in residual potential in repeated tests of a photographic photoreceptor made of 51 ml.

Claims (1)

【特許請求の範囲】 β型銅フタロシアニンを電荷発生剤とした積層型電子写
真用感光体において、電荷搬送層の主成分が、下記一般
式( I )で表わされる化合物100重量部当り、一般
式(II)で表わされる化合物0.8〜5.0重量部配合
して成ることを特徴とする電子写真用感光体。 一般式▲数式、化学式、表等があります▼( I ) (式( I )において、R_1は炭素数2〜4のアルキ
ル基、R_2はアリール基又はアルキル置換アリール基
である。) 一般式▲数式、化学式、表等があります▼(II) (式(II)において、R_1は炭素数2〜4のアルキル
基、R_2は炭素数2〜4のアルキル基又はアリール基
又はアルキル置換アリール基、R_3はアリール基又は
ベンジル基である。)
[Scope of Claims] In a laminated electrophotographic photoreceptor using β-type copper phthalocyanine as a charge generating agent, the main component of the charge transport layer is a compound represented by the following general formula (I) per 100 parts by weight of a compound represented by the general formula (I). An electrophotographic photoreceptor comprising 0.8 to 5.0 parts by weight of the compound represented by (II). General formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) (In formula (I), R_1 is an alkyl group having 2 to 4 carbon atoms, and R_2 is an aryl group or an alkyl-substituted aryl group.) General formula ▲ Numerical formula , chemical formulas, tables, etc.▼(II) (In formula (II), R_1 is an alkyl group with 2 to 4 carbon atoms, R_2 is an alkyl group or aryl group with 2 to 4 carbon atoms, or an alkyl-substituted aryl group, and R_3 is an alkyl-substituted aryl group with 2 to 4 carbon atoms. (aryl group or benzyl group)
JP25978485A 1985-11-21 1985-11-21 Electrophotographic sensitive body Pending JPS62121459A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP25978485A JPS62121459A (en) 1985-11-21 1985-11-21 Electrophotographic sensitive body

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP25978485A JPS62121459A (en) 1985-11-21 1985-11-21 Electrophotographic sensitive body

Publications (1)

Publication Number Publication Date
JPS62121459A true JPS62121459A (en) 1987-06-02

Family

ID=17338930

Family Applications (1)

Application Number Title Priority Date Filing Date
JP25978485A Pending JPS62121459A (en) 1985-11-21 1985-11-21 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPS62121459A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0345005A2 (en) * 1988-05-31 1989-12-06 Somar Corporation Electrophotographic photosensitive element and method of preparing same
EP0437310A2 (en) * 1990-01-08 1991-07-17 Hitachi, Ltd. Photosensitive element for electrophotography
JPH0530269U (en) * 1991-09-25 1993-04-20 株式会社イナツクス Water faucet
JPH0530260U (en) * 1991-09-27 1993-04-20 株式会社イナツクス Water faucet

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0345005A2 (en) * 1988-05-31 1989-12-06 Somar Corporation Electrophotographic photosensitive element and method of preparing same
EP0437310A2 (en) * 1990-01-08 1991-07-17 Hitachi, Ltd. Photosensitive element for electrophotography
JPH0530269U (en) * 1991-09-25 1993-04-20 株式会社イナツクス Water faucet
JPH0530260U (en) * 1991-09-27 1993-04-20 株式会社イナツクス Water faucet

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