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JPH0272370A - Electrophogoraphic sensitive body - Google Patents

Electrophogoraphic sensitive body

Info

Publication number
JPH0272370A
JPH0272370A JP22400788A JP22400788A JPH0272370A JP H0272370 A JPH0272370 A JP H0272370A JP 22400788 A JP22400788 A JP 22400788A JP 22400788 A JP22400788 A JP 22400788A JP H0272370 A JPH0272370 A JP H0272370A
Authority
JP
Japan
Prior art keywords
carrier
photoreceptor
pyrazine
layer
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.)
Pending
Application number
JP22400788A
Other languages
Japanese (ja)
Inventor
Yumi Matsuzawa
松澤 由美
Kazumasa Watanabe
一雅 渡邉
Hisahiro Hirose
尚弘 廣瀬
Akihiko Itami
明彦 伊丹
Kiyoshi Sawada
潔 澤田
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 JP22400788A priority Critical patent/JPH0272370A/en
Publication of JPH0272370A publication Critical patent/JPH0272370A/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
    • G03G5/0622Heterocyclic compounds
    • G03G5/0624Heterocyclic compounds containing one hetero ring
    • G03G5/0635Heterocyclic compounds containing one hetero ring being six-membered
    • G03G5/0638Heterocyclic compounds containing one hetero ring being six-membered containing two hetero atoms

Landscapes

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

Abstract

PURPOSE:To obtain the excellent photosensitive body which has high sensitivity and the stable characteristics at the time of repetitive use and has no toxicity by providing the photosensitive body contg. a specific compd. on a conductive base. CONSTITUTION:The photosensitive layer contg. the pyrazine deriv. expressed by formula I is provided. In formula I, Pz is expressed by formula II or formula III; R to R<4> denote alkyl group, aryl group all of R1 to R4 are preferably the same substituent. Such pyrazine compd. is used as the photoconductive material of the electrophotographic sensitive body and this pyrazine compd. is used a the carrier transfer material of the separated-function type electrophotographic sensitive body which executes carrier generation and transfer with respectively separate materials. The electrophotographic sensitive body which has excellent film properties, has excellent electrophotographic characteristics such as charge holding power, sensitivity and residual potential, has less fatigue deterioration when subjected to repetitive use and exhibits stable characteristics to heat or light as well is obtd. in this way.

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電子写真感
光体に関する。
DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing an organic photoconductive compound as a main component.

〔従来の技術〕[Conventional technology]

従来、電子写真感光体(以下単に感光体と称する場合も
ある)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。
Conventionally, electrophotographic photoreceptors (hereinafter sometimes simply referred to as photoreceptors) include selenium, zinc oxide, cadmium sulfide,
Inorganic photoreceptors having a photosensitive layer mainly composed of an inorganic photoconductive compound such as silicon have been widely used.

しかしこれらは、感度、熱安定性、耐久性等において必
ずしも満足し得るものではない。
However, these are not necessarily satisfactory in terms of sensitivity, thermal stability, durability, etc.

例えば、セレンは結晶化すると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、又熱や指紋等が原
因となり結晶化し、感光体としての性能が劣化してしま
う。又硫化カドミウムでは耐湿性や耐久性、酸化亜鉛で
も耐久性等に問題がある。
For example, when selenium crystallizes, its properties as a photoreceptor deteriorate, making it difficult to manufacture.Also, selenium crystallizes due to heat, fingerprints, etc., and its performance as a photoreceptor deteriorates. In addition, cadmium sulfide has problems in moisture resistance and durability, and zinc oxide has problems in durability, etc.

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をする有機感
光体の開発・研究が近年盛んに行われている。例えば特
公昭50−10496号にはポリ・N−ビニル力ルバゾ
ールと2.4.7− トリニトロ−9−フルオレノンを
含をする感光層を有する有機感光体の記載がある。しか
しこの感光体は、感度及び耐久性において必ずしも満足
できるものではない。このような欠点を改良するために
キャリア発生機能どキャリア輸送機能とを異なる物質に
分担させ、より高性能の有機感光体を開発する試みがな
されている。このようないわゆる機能分離型の感光体は
、それぞれ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 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. For example, Japanese Patent Publication No. 50-10496 describes an organic photoreceptor having a photosensitive layer containing poly-N-vinyl rubazole and 2,4,7-trinitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability. In order to improve these drawbacks, attempts have been made to develop organic photoreceptors with higher performance by assigning carrier generation and carrier transport functions to different substances. For such so-called functionally separated photoreceptors, each material can be selected from a wide range.
Many studies have been conducted since it is possible to relatively easily create a photoreceptor with arbitrary performance.

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。一方キャリア輸送物質に
ついても、例えば特開昭51−94829号、同52−
72231号、同53−27033号、同55−520
63号、同58−65440号等に開示されているごと
く各種にわたる物質が提案されている。
As a result, various azo compounds have been developed and put into practical use as carrier-generating substances. On the other hand, regarding carrier transport substances, for example, JP-A-51-94829, JP-A-52-
No. 72231, No. 53-27033, No. 55-520
A wide variety of substances have been proposed, as disclosed in No. 63, No. 58-65440, and the like.

〔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て作成した電子
写真感光体には比較的優れた電子写真的性能を示すもの
もあるが、その光、或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の不安定、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、
更に優れたキャリア輸送機能を有しかつ長期間の使用に
対して安定した性能を示すキャリア輸送物質の開発が望
まれていた。
Although some electrophotographic photoreceptors made using carrier transport materials such as those described above exhibit relatively excellent electrophotographic performance, their durability against light or electrical loads is weak, and their durability during repeated use is poor. It does not fully satisfy practical requirements because it causes instability and deterioration of performance.
There has been a desire to develop a carrier transport material that has even better carrier transport functionality and exhibits stable performance over long periods of use.

更に近年感光体の光源としてArレーザ、He−Neレ
ーザ等の気体レーザや半導体レーザが使用され始めてい
る。これらのレーザはその特徴として時系列ON/ O
FFが可能であり、インテリジェントコピアをはじめと
する画像処理機能を有する複写機やコンピュータのアウ
トプット用のプリンターの光源として特に有望視されて
いる。中でも半導体レーザはその性質上音響工学素子等
の電気信号/光信号の変換素子が不要であることや小型
・軽量化が可能であることなどから注目を集めている。
Furthermore, in recent years, gas lasers such as Ar lasers and He--Ne lasers and semiconductor lasers have begun to be used as light sources for photoreceptors. These lasers are characterized by time series ON/O
It is capable of FF and is particularly promising as a light source for copying machines and computer output printers that have image processing functions, including intelligent copiers. Among these, semiconductor lasers are attracting attention because their nature does not require electrical signal/optical signal conversion elements such as acoustic engineering elements, and they can be made smaller and lighter.

しかしこの半導体レーザは気体レーザに比較して低出力
であり、又発振波長も長波長(約780nm以上)であ
ることから従来の感光体では分光感度が短波長側により
過ぎており、このままでは半導体レーザを光源とする機
器への適用は困難であり、キャリア輸送物質についても
新たな改良が要求されていた。
However, this semiconductor laser has a low output compared to a gas laser, and the oscillation wavelength is also long (approximately 780 nm or more), so the spectral sensitivity of conventional photoreceptors is too high on the short wavelength side. It is difficult to apply this method to devices that use lasers as light sources, and new improvements have been required for carrier transport materials.

本発明はこうした問題を解決し極めて耐久性の高い電子
写真感光体を提供すべく行われたものである。
The present invention has been made to solve these problems and provide an electrophotographic photoreceptor with extremely high durability.

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

前記の問題は導電性支持体に下記一般式〔I〕で表され
るピラジン誘導体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を用いることにより解決される。
The above problem can be solved by using an electrophotographic photoreceptor characterized in that the conductive support has a photosensitive layer containing a pyrazine derivative represented by the following general formula [I].

一般式〔I〕 R、、R、、R、及びR6はアルキル基、アリール基を
表す。
General formula [I] R, , R, , R and R6 represent an alkyl group or an aryl group.

又上記一般式[1)中のR、、R2,R、及びR4が全
て同一の置換基である。ことが好ましい。
Further, R, , R2, R, and R4 in the above general formula [1] are all the same substituent. It is preferable.

〔発明の効果〕〔Effect of the invention〕

本発明においては一般式(I)で示されるピラジン誘導
体を電子写真感光体の光導電性物質として用いることに
より、又これをキャリア発生と輸送とをそれぞれ別個の
物質で行う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く、かつ熱或いは光
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。
In the present invention, by using a pyrazine derivative represented by the general formula (I) as a photoconductive substance of an electrophotographic photoreceptor, this can be used for functionally separated electrophotography in which carrier generation and transport are performed using separate substances, respectively. By using it as a carrier transport material in the body, it has excellent film physical properties and excellent electrophotographic properties such as charge retention, sensitivity, and residual potential, and has little fatigue deterioration even after repeated use, and is resistant to heat or light. However, it is possible to create an electrophotographic photoreceptor that can exhibit stable characteristics.

又本発明で用いられるピラジン誘導体は前記一般式〔I
〕で示されるピラジン誘導体の中から単独或いは2種類
以上の組合せで用いることができ、又他の光導電性物質
との組合せで使用してもよい。
Furthermore, the pyrazine derivative used in the present invention has the general formula [I
The pyrazine derivatives shown in ] can be used alone or in combination of two or more, and may also be used in combination with other photoconductive substances.

前記−最大〔■〕で示される本発明に有効なピラジン誘
導体の具体例としては、下記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化合物が限定され
るものではない。
Specific examples of the pyrazine derivatives indicated by the maximum [■] above that are effective in the present invention include those having the following structural formula, but the compounds according to the present invention are not limited thereto.

例示化合物(1) 一般式CI)で表される化合物中−最大[11)の構造
を有するもの 一般式(n) 例示化合物(2) 一般式〔I)で表される化合物中−最大の構造を有する
もの 一般式(III) (III) 前記のごとき本発明の化合物はそれ自体としては可視光
に対してほとんど感光性を有しないがある種の増感方法
を適用することにより可視光に対する光導電性を付与し
単独で感光体を形成せしめることができる。その第一の
方法は、有機染料を添加し、分光増感(色素増感)を行
う方法である。
Exemplified Compound (1) Among the compounds represented by general formula CI), those having the maximum structure [11] General formula (n) Exemplary Compound (2) Among the compounds represented by general formula [I], the maximum structure A compound having the general formula (III) (III) Although the compound of the present invention as described above has almost no photosensitivity to visible light as such, it can be sensitive to visible light by applying a certain sensitization method. It imparts electrical conductivity and can be used alone to form a photoreceptor. The first method is to add an organic dye and perform spectral sensitization (dye sensitization).

第二の方法は電荷移動錯体を形成せしめて増感する方法
である。分光増感に用いられる色素としては下記のよう
なものが挙げられる。
The second method is to form a charge transfer complex and sensitize it. Examples of dyes used for spectral sensitization include the following.

(1)メチルバイオレット、クリスタルバイオレット、
マラカイトグリーンなどのトリフェニルメタン系色素 (2)  エリスロシン、ローズベンガルなどのキサン
チン系色素 (3) メチルブルー メチレングリーンなどのチアジ
ン系色素 (4)カブリブルー、メルトラブル−などのオキサジン
系色素 (5)チアシアニン、オキサシアニンなどのシアニン系
色素 (6)p−ジメチルアミノスチリルキノリンなどのスチ
リル系色素 (7) ピリリウム塩、チアピリリウム塩、ベンゾピリ
リウム塩などのピリリウム塩系色素(8)  3.3’
−ジカルバゾリルメタン系色素又本発明の化合物と電荷
移動錯体と形成し得る電子受容性物質としては、2.4
.7− トリニトロフルオレノン、2,4,5.7−チ
トラニトロフルオレノン、クロラニル、テトラシアノキ
ノジメタンなどのルイス酸が用いられる。
(1) Methyl violet, crystal violet,
Triphenylmethane dyes such as malachite green (2) Xanthine dyes such as erythrosine and rose bengal (3) Thiazine dyes such as methyl blue and methylene green (4) Oxazine dyes such as Cabri Blue and Melt Lab (5) Cyanine dyes such as thiacyanine and oxacyanine (6) Styryl dyes such as p-dimethylaminostyrylquinoline (7) Pyrylium salt dyes such as pyrylium salt, thiapyrylium salt, and benzopyrylium salt (8) 3.3'
-Dicarbazolylmethane dyes or electron-accepting substances that can be formed with the compound of the present invention and a charge transfer complex include 2.4
.. Lewis acids such as 7-trinitrofluorenone, 2,4,5.7-titranitrofluorenone, chloranil, and tetracyanoquinodimethane are used.

しかしながら本発明の化合物は、そのキャリア輸送能の
みを利用し、他の有機染料、顔料或いは無機光導電体等
のキャリア発生能を有するキャリア発生物質と組合せ、
機能分離型感光体とした場合最も好ましい効果が得られ
る。
However, the compound of the present invention utilizes only its carrier transport ability and can be combined with other carrier-generating substances such as organic dyes, pigments, or inorganic photoconductors that have a carrier-generating ability.
The most favorable effect can be obtained when a functionally separated photoreceptor is used.

キャリア発生物質としては前記(1)〜(8)に示した
色素も有用であるが、その佐久のような物が上げられる
The dyes shown in (1) to (8) above are also useful as carrier-generating substances, and examples include those such as Saku.

(1)  モノアゾ色素、ジスアゾ色素、トリスアゾ色
素などのアゾ系色素 (2)ペリレン酸無水物、ペリレン酸イミドなどのペリ
レン系色素 (3)インジゴ、チオインジゴなどのインジゴ系色素 (4)  アンスラキノン、ピレンキノン及びフラバン
フロン類などの多環キノン類 (5)キナクリドン系色素 (6) ビスベンゾイミダゾール系色素(7)インダス
ロン系色素 (8) スクェアリリウム系色素 (9)  金属フタロンアニン、無金属フタロンアニン
などの7りロシアニン系色素 (10)セレン、セレン合金 (H)CdS、CdSe、非晶質シリコンなトノ無機光
導電体 (12)ピリリウム塩色素、チアピリリウム塩色素とポ
リカーボネートから形成される共晶錯体本発明において
用いられるトリフェニルアミン誘導体は、それ自体では
被覆形成能がないため、種々の結着剤を組合せて感光層
が形成される。
(1) Azo dyes such as monoazo dyes, disazo dyes, and trisazo dyes (2) Perylene dyes such as perylenic anhydride and perylenic acid imide (3) Indigo dyes such as indigo and thioindigo (4) Anthraquinone and pyrenequinone and polycyclic quinones such as flavanfluorones (5) quinacridone dyes (6) bisbenzimidazole dyes (7) induthrone dyes (8) squarelylium dyes (9) metal phthalonanine, metal-free phthalonanine, etc. Lycyanine dye (10) Selenium, selenium alloy (H) CdS, CdSe, amorphous silicon inorganic photoconductor (12) Pyrylium salt dye, eutectic complex formed from thiapyrylium salt dye and polycarbonate In the present invention Since the triphenylamine derivative used does not have the ability to form a coating by itself, a photosensitive layer is formed by combining various binders.

ここ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、疎水性で誘電率が高く、電気絶縁性フィ
ルム形成性高分子重合体を用いるのが好ましい。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 here, it is preferable to use a hydrophobic, high dielectric constant, 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 (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)スチレン系共重合樹脂(例えばスチレンブタジェ
ン共重合体、スチレンメタクリル酸メチル共重合体) (10)アクリルニトリル系共重合樹脂(例えば塩化ビ
ニリデン−アクリル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)  シリコーン樹脂 (14)  シリコーン樹脂−アルキッド樹脂(15)
  フェノール樹脂(例えばフェノールーホルムアルデ
ビト樹脂、m−クレゾールーホルムアルデビト樹脂等) (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)ポリビニルブチロール (19)  ホリビニルフオルマール これらの結着剤は、単独で或いは2種以上の混合物とし
て用いることができる。
(1) Polycarbonate (2) Polyester (3) Methacrylic resin (4) Acrylic resin (5) Polyvinyl chloride (6) Polyvinylidene chloride (7) Polystyrene (8) Polyvinyl acetate (9) Styrenic copolymer resin (e.g. styrene butadiene copolymer, styrene methyl methacrylate copolymer) (10) Acrylonitrile copolymer resin (e.g. vinylidene chloride-acrylonitrile copolymer, etc.) (11)
Vinyl chloride-vinyl acetate copolymer (12) Vinyl chloride-
Vinyl acetate-maleic anhydride copolymer (13) Silicone resin (14) Silicone resin-alkyd resin (15)
Phenol resin (e.g. phenol-formaldevit resin, m-cresol-formaldevit resin, etc.) (16) Styrene-alkyd resin (17) Poly-
N-Vinylcarbazole (18) Polyvinylbutyrol (19) Polyvinyl formal These binders can be used alone or as a mixture of two or more.

本発明の感光体は、第1図及び第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と本発明のスチリルトリフェニルアミン誘
導体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。第3
図及び第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。このよ
うに感光層4を二層構成したときに最も優れた電子写真
特性を有する電子写真感光体が得られる。
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 and a styryltriphenylamine derivative of the present invention on a conductive support l for carrier transport. A photosensitive layer 4 made of a laminate with a carrier transport layer 3 containing a substance as a main component is provided. Third
As shown in the drawings and FIG. 4, this photosensitive layer 4 may be provided through an intermediate layer 5 provided on a conductive support l. When the photosensitive layer 4 has a two-layer structure in this manner, an electrophotographic photoreceptor having the most excellent electrophotographic properties can be obtained.

又本発明においては、第5図及び第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上に直接或いは中間層5を介して設けてもよい。
Further, in the present invention, as shown in FIGS. 5 and 6, a photosensitive layer 4 formed by dispersing a fine particulate carrier generating substance 7 in a layer 6 containing the carrier transporting substance as a main component is used as a conductive support. It may be provided directly on the layer 1 or via an intermediate layer 5.

又キャリア発生物質を使わずに、キャリア輸送物質に増
感染料或いはルイス酸等を加えて、第5図及び第6図と
同様に単層の感光層4を設けても好ましい結果が得られ
る。
Preferable results can also be obtained by adding a sensitizing dye or a Lewis acid to a carrier transporting material and forming a single photosensitive layer 4 as shown in FIGS. 5 and 6, without using a carrier-generating material.

ここで感光層4を二層構成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、これは当該キャリア輸送
層3中のスチリルトリフェニルアミン誘導体が正孔に対
して高い輸送能を有する物質であるからである。
Here, when the photosensitive layer 4 is composed of two layers, the carrier generation layer 2
Which of the carrier transport layer 3 and the carrier transport layer 3 should 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 styryltriphenylamine derivative in the carrier transport layer 3 is a substance that has a high transport ability for holes.

又二層構成の感光層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上に直接或い
は必要に応じて接着層もしくはバリヤー層などの中間層
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, the carrier generation layer 2 constituting the photosensitive layer 4 having a two-layer structure is
It can be formed directly on the conductive support 1 or the carrier transport layer 3, or after providing an intermediate layer such as an adhesive layer or a barrier layer as 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。
(1) Vacuum evaporation method (2) A method in which a solution of a carrier-generating substance dissolved in a suitable solvent is applied.

(3)キャリア発生物質をボールミル、ホモミキサー等
によって分散媒中で微細粒子状とし、必要に応じて結着
剤と混合分散して得られる分散液を塗布する方法。
(3) A method in which a carrier-generating substance is made into fine particles in a dispersion medium using a ball mill, a homomixer, etc., and a dispersion obtained by mixing and dispersing with a binder as necessary is applied.

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.O1〜5μlであることが好ましく、更に好ましく
は0.05〜3μmである。
The thickness of the carrier generation layer 2 formed in this way is
0. It is preferably 01 to 5 μl, more preferably 0.05 to 3 μm.

又キャリア輸送層3の厚さは必要に応じて変更し得るが
、通常5〜30μmであることが好ましい。
Further, the thickness of the carrier transport layer 3 can be changed as necessary, but it is usually preferably 5 to 30 μm.

このキャリア輸送層3における組成割合は、本発明のス
チリルトリフェニルアミン誘導体を主成分とするキャリ
ア輸送物質1重量部に対して結着剤を0.8〜IO重量
部とするのが好ましいが、微粉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51L量部以下の範囲で
用いることが好ましい。
The composition ratio in this carrier transport layer 3 is preferably 0.8 to IO parts by weight of the binder to 1 part by weight of the carrier transport material whose main component is the styryltriphenylamine derivative of the present invention. When forming the photosensitive layer 4 in which a fine powder carrier-generating substance is dispersed, it is preferable to use the binder in an amount of 51 L parts or less per 1 part by weight of the carrier-generating substance.

又キャリア発生層2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ましい。
Further, when the carrier generation layer 2 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.

l) アルミニウム板、ステンレス板などの金属板。l) Metal plates such as aluminum plates and stainless steel plates.

2) 紙或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 paper or plastic film by lamination or vapor deposition.

3) 紙或いはプラスチックフィルムなどの支持体上に
、導電性ポリマー、酸化インジウム、酸化錫などの導電
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.

接着層或いはバリヤー層などの中間層5としては、前述
結着剤として用いられる高分子重合体の他、ゼラチン、
カゼイン、澱粉、ポリビニルアルコール、酢酸ビニル、
エチルセルロース、カルボキシメチルセルロースなどの
有機高分子物質又は酸化アルミニウムなとが用いられる
For the intermediate layer 5 such as an adhesive layer or a barrier layer, in addition to the high molecular weight polymer used as the binder, gelatin,
casein, starch, polyvinyl alcohol, vinyl acetate,
Organic polymer substances such as ethyl cellulose and carboxymethyl cellulose, or aluminum oxide are used.

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I;ものである。
The photoreceptor of the present invention has the above-mentioned structure, and as is clear from the examples described later, it has excellent charging characteristics, sensitivity characteristics, and image forming characteristics.

〔実施例〕〔Example〕

以下、本発明の実施例で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。
The present invention will be specifically explained below using Examples, but the embodiments of the present invention are not limited thereto.

合成例1 化合物例A−2の合成 本発明の前記一般式〔I〕で表されるビスアゾ化合物は
公知の方法により容易に合成できる。
Synthesis Example 1 Synthesis of Compound Example A-2 The bisazo compound represented by the general formula [I] of the present invention can be easily synthesized by a known method.

J、L、Leiserson、 A、Weisberg
er、 Org、5ynth、。
J., L., Leiserson, A., Weisberg.
er, Org, 5ynth,.

Co11.VolI[I 、 183 (1955)に
記載される方法に従って、4−クロルアセチルアセトア
ニリドを合成し、これから特開昭62−270623号
を参考にして下記のようにピラジン化合物を合成した。
Co11. 4-chloroacetylacetanilide was synthesized according to the method described in VolI[I, 183 (1955), and a pyrazine compound was synthesized from it as described below with reference to JP-A-62-270623.

160gのp−クロルアセチルアセトアニリドを1.5
12のジメチルアセトアシドに溶解し、0°Cに冷却し
た。上記溶液に乾燥アンモニアを飽和させ、室温に昇温
して2時間、次に68〜70’Oで2時間、更に還流条
件に昇温し12時間反応させた。反応溶液が熱いうちに
300aαの水を加え室温まで冷却し、生成した結晶を
濾別した。収量は350gであっt;。
160g of p-chloroacetylacetanilide to 1.5
12 in dimethylacetoacide and cooled to 0°C. The above solution was saturated with dry ammonia, heated to room temperature for 2 hours, then heated to 68-70'O for 2 hours, and then heated to reflux conditions for 12 hours. While the reaction solution was still hot, 300 aα of water was added thereto, cooled to room temperature, and the formed crystals were separated by filtration. Yield was 350g.

この結晶は2,5−ビス(4−アセトアシドフェニル)
ピラジンである。反応溶液の濾液に更に水1.2ffを
加えると更に結晶が析出した。これをDMAC/水−X
の混合溶媒で再結晶し27.6gの結晶を得た。これは
2.6−ビス(4−アセトアシドフェニル)ピラジンで
ある。ここで得られた2、6−ビス(4−アセトアシド
フェニル)ピラジン10.38g (0,03モル)を
濃塩酸120+I2に分散し4時間還流加熱した放冷後
、析出した固体を濾別し、水200m12に分散した。
This crystal is 2,5-bis(4-acetoacidophenyl)
It is pyrazine. When 1.2 ff of water was further added to the filtrate of the reaction solution, further crystals were precipitated. This is DMAC/Water-X
Recrystallization was performed using a mixed solvent of 27.6 g of crystals. This is 2,6-bis(4-acetoacidophenyl)pyrazine. 10.38 g (0.03 mol) of the 2,6-bis(4-acetoacidophenyl)pyrazine obtained here was dispersed in concentrated hydrochloric acid 120+I2 and heated under reflux for 4 hours. After cooling, the precipitated solid was separated by filtration. , dispersed in 200 m12 of water.

固体の苛性ソーダを加えて強アルカリ性とし、生成物を
濾別した。生成物はDMAC/水から再結晶した。収量
は7.65gである。この生成物は2 、5−、ビス(
4−アミノフェニル)ピラジンである。
Solid caustic soda was added to make the mixture strongly alkaline, and the product was filtered off. The product was recrystallized from DMAC/water. Yield is 7.65g. This product is 2,5-,bis(
4-aminophenyl) pyrazine.

以上で得られた2、5−ビス(4−アミノフェニル)ピ
ラジン5.24g(0,02モル)をエタノール20m
12に分散し、沃化エチル6.24gを滴下し、3時間
還流を行っj二。
5.24 g (0.02 mol) of 2,5-bis(4-aminophenyl)pyrazine obtained above was added to 20 ml of ethanol.
12, 6.24 g of ethyl iodide was added dropwise, and the mixture was refluxed for 3 hours.

常温になった後、10%の水酸化ナトリウム溶液を10
0m12加え1時間撹拌しI:後、トルエンで抽出し、
水洗を行い、溶媒を留去した後、シリカゲル・クロマト
グラフィにて精製を行った。
After reaching room temperature, add 10% sodium hydroxide solution to 10%
Add 0ml and stir for 1 hour. After that, extract with toluene,
After washing with water and distilling off the solvent, purification was performed using silica gel chromatography.

得られた目的物の収量は、3.54gであった。The yield of the target product obtained was 3.54 g.

目的物である2、5−ビス(4−ジエチルフェニル)ピ
ラジンはFDマススペクトルにより確認を行った結果、
目的物であることが確認された。
The target product, 2,5-bis(4-diethylphenyl)pyrazine, was confirmed by FD mass spectroscopy.
The target was confirmed.

実施例1 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セレンを蒸着して厚さ0.5
μmのキャリア発生層を形成させた。
Example 1 Selenium was evaporated onto a conductive support consisting of a polyester film laminated with aluminum foil to a thickness of 0.5
A carrier generation layer of μm was formed.

その上に例示化合物A−2,6重量部とポリカーボネー
ト「パンライトL−12504(奇人化成社製)10重
量部とを1.2−ジクロルエタン90重量部中に溶解し
、この溶液を乾燥後の膜厚が11pm+になるように塗
布して、キャリア輸送層を形成し、本発明の電子写真感
光体を作成した。
On top of that, 2.6 parts by weight of Exemplified Compound A and 10 parts by weight of polycarbonate "Panlite L-12504 (manufactured by Kijin Kasei Co., Ltd.) were dissolved in 90 parts by weight of 1,2-dichloroethane, and this solution was dried. A carrier transport layer was formed by coating to a film thickness of 11 pm+, and an electrophotographic photoreceptor of the present invention was prepared.

この電子写真感光体について、静電複写紙試験装置r 
EPA −,5100型J ((株)川口電機製作所製
)を用いてダイナミック方式で電子写真特性を測定した
。即ち前記感光体の感光層表面を帯電圧−6KVで5秒
間帯電せしめた時の表面電位VA1次いでタングステン
ランプの光を感光体表面における照度が35f2uxに
なるようにして照射し、表面電位vAを半分に減衰させ
るのに要する露光量(半減露光量)E ’A (Qux
−sec)並びに30(lux−secの露光量で照射
した後の表面電位(残留電位)Vi+をそれぞれ求めた
。又同じ測定を100回繰返して行った。
Regarding this electrophotographic photoreceptor, electrostatic copying paper tester r
The electrophotographic properties were measured using a dynamic method using EPA-5100 Model J (manufactured by Kawaguchi Electric Seisakusho Co., Ltd.). That is, when the surface of the photosensitive layer of the photoreceptor is charged with a charging voltage of -6 KV for 5 seconds, the surface potential VA1 is then irradiated with light from a tungsten lamp so that the illumination intensity on the photoreceptor surface is 35f2ux, and the surface potential vA is reduced by half. Exposure amount required to attenuate (half-reduced exposure amount) E 'A (Qux
The surface potential (residual potential) Vi+ after irradiation with an exposure dose of -sec) and 30 (lux-sec) was determined.The same measurement was repeated 100 times.

第1表 この表から明らかなように、本発明の電子写真感光体は
十分な電荷保持力を有し、高感度で残留電位が小さくが
っ繰返し使用においても良好な特性が保たれ電子写真感
光体として優れた特性を有している。
Table 1 As is clear from this table, the electrophotographic photoreceptor of the present invention has sufficient charge retention ability, has high sensitivity, has a small residual potential, and maintains good characteristics even after repeated use. It has excellent physical properties.

比較例1 キャリア輸送物質として例示化合物A−2の代りに下記
化合物T−1を用いIこ他は実施例1と同様にして比較
用感光体を作成した。
Comparative Example 1 A comparative photoreceptor was prepared in the same manner as in Example 1 except for using Compound T-1 below instead of Exemplified Compound A-2 as a carrier transport material.

CH。CH.

この感光体について、実施例1と同様にして測定を行っ
たところ、第2表の結果を得た。
When this photoreceptor was measured in the same manner as in Example 1, the results shown in Table 2 were obtained.

第2表 以上の結果より明らかなように、比較用感光体は実施例
1の本発明の感光体に比べ繰返し使用時の安定性におい
て著しく劣ったものである。
As is clear from the results in Table 2 and above, the comparative photoreceptor was significantly inferior in stability during repeated use compared to the photoreceptor of the present invention of Example 1.

実施例2〜4 キャリア発生物質として例示化合物A−2の代りに例示
化合物A−4、A−10,A−12ヲ用u’だ他は実施
例1と同様にして本発明の電子写真感光体を作成した。
Examples 2 to 4 The electrophotographic photosensitive material of the present invention was produced in the same manner as in Example 1 except that exemplified compounds A-4, A-10, and A-12 were used as carrier generating substances in place of exemplified compound A-2. Created a body.

これらの感光体について実施例Iにおけると同様にして
本発明の電子写真感光体を作成した。
Electrophotographic photoreceptors of the present invention were prepared using these photoreceptors in the same manner as in Example I.

これらの感光体について実施例1におけると同様にして
初期特性を測定したところ第3表の結果を得た。
The initial characteristics of these photoreceptors were measured in the same manner as in Example 1, and the results shown in Table 3 were obtained.

実施例5 ポリエステルフィルム上にアルミニウムを蒸着した導電
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M F −104(漬水化学社製
)より成る厚さ0.05μmの中間層を設け、その上に
ジブロムアンスアンスロン「モノライトレッド2 YJ
 (C,1,NO,59300IC1社製)lli量部
を1.2−ジクロルエタン30重量部に加えてボールミ
ルで分散して得られた分散液にポリカーボネート「パン
ライトL−1250J(奇人化成社製)1.5重量部に
溶解し、十分混合した塗布液を乾燥後の膜厚が2μIに
なるように塗布してキャリア発生層を形成した。
Example 5 A 0.05 μm thick film made of vinyl chloride-vinyl acetate-maleic anhydride copolymer [S-LEC MF-104 (manufactured by Tsukisui Kagaku Co., Ltd.)] was deposited on a conductive support having aluminum deposited on a polyester film. An intermediate layer is provided, and on top of that, Dibrom Ansu Anthrone ``Monolite Red 2 YJ
(C, 1, NO, 59300 manufactured by IC1) was added to 30 parts by weight of 1,2-dichloroethane and dispersed in a ball mill. Polycarbonate "Panlite L-1250J (manufactured by Kijin Kasei Co., Ltd.) was added to the resulting dispersion. A carrier-generating layer was formed by dissolving 1.5 parts by weight of a coating solution and thoroughly mixing the coating solution so that the film thickness after drying was 2 μI.

その上に例示化合物A−10.6重量部とポリエステル
「バイロン200J (東洋紡績社製)10重量部とを
1.2−ジクロルエタン90重量部に溶解した溶液を乾
燥後の膜厚が11μmになるように塗布して、ギヤリア
輸送層を形成し、本発明の電子写真感光体を作成した。
On top of that, a solution of 10.6 parts by weight of Exemplary Compound A and 10 parts by weight of polyester "Vylon 200J (manufactured by Toyobo Co., Ltd.) dissolved in 90 parts by weight of 1,2-dichloroethane was dried to give a film thickness of 11 μm. The electrophotographic photoreceptor of the present invention was prepared by applying the following coating to form a gear transport layer.

この感光体について実施例1におけると同様にして測定
を行ったところ第4表の結果を得た。
Measurements were carried out on this photoreceptor in the same manner as in Example 1, and the results shown in Table 4 were obtained.

比較例2 キャリア輸送物質として、例示化合物A−10の代わり
に下記化合物T−2を用いた他は実施例5と同様にして
、比較用感光体を作成した。
Comparative Example 2 A comparative photoreceptor was prepared in the same manner as in Example 5, except that Compound T-2 below was used instead of Exemplary Compound A-10 as a carrier transport material.

この比較用感光体について実施例1におけると同様にし
て測定したところ第5表の結果を得た。
When this comparative photoreceptor was measured in the same manner as in Example 1, the results shown in Table 5 were obtained.

第5表 以上の結果から明らかなように比較用感光体は発明の化
合物に比べ感度並びに繰返しの安定性において著しく劣
ったものである。
As is clear from the results in Table 5 and above, the comparative photoreceptor was significantly inferior in sensitivity and repeated stability compared to the compound of the invention.

実施例6 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
した導電性支持体上にポリエステル「バイロン200J
 (東洋紡蹟社製)より成る厚さ0.1μmの中間層を
設けた。
Example 6 Polyester “Vylon 200J” was placed on a conductive support made by laminating aluminum foil on a polyester film.
(manufactured by Toyo Boseki Co., Ltd.) with a thickness of 0.1 μm was provided.

その上のキャリア発生物質として下記構造式で表される
アゾ顔料1重量部を1.2−ジクロルエタン60重i部
に分散した液を乾燥後の膜厚が0.3μmになるように
して塗布しキャリア発生層を形成した。
As a carrier generating substance, a solution prepared by dispersing 1 part by weight of an azo pigment represented by the following structural formula in 60 parts by weight of 1,2-dichloroethane was applied on top of the carrier-generating substance so that the film thickness after drying was 0.3 μm. A carrier generation layer was formed.

更にその上に例示化合物A−13,6重量部とポリカー
ボネート樹脂rZ−200J(三菱ガス化学社製)10
重量部とを1.2−ジクロルエタン90重量部に溶解し
t;液を乾燥後の膜厚が20μmになるように塗布して
キャリア輸送層を形成し、本発明の電子写真感光体を作
成した。この感光体について、実施例1と同様にして初
期特性を測定を行ったところV A−1280v、  
E ’A −3,3ffux−sea及びV m = 
Ovであった。
Furthermore, 13.6 parts by weight of Exemplified Compound A-1 and 10 parts by weight of polycarbonate resin rZ-200J (manufactured by Mitsubishi Gas Chemical Co., Ltd.)
parts by weight were dissolved in 90 parts by weight of 1,2-dichloroethane, and the solution was applied so that the film thickness after drying was 20 μm to form a carrier transport layer, thereby producing an electrophotographic photoreceptor of the present invention. . The initial characteristics of this photoreceptor were measured in the same manner as in Example 1, and found to be VA-1280v.
E'A -3,3ffux-sea and V m =
It was Ov.

実施例7 キャリア発生物質として下記化合物を用いた他は実施例
6と同様にした本発明の電子写真感光体を作成した。
Example 7 An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 6 except that the following compound was used as a carrier generating substance.

又この感光体を電子写真複写機r U −B ix15
50MRJ (コニカ株式会社製)に装着し実写テスト
を行ったところ原画に忠実でコントラストが高く階調性
に優れかつ鮮明な複写画像を得た。これは5000回繰
返しても初期と変わらない良好な複写画像を得t;。
Also, this photoreceptor is used in an electrophotographic copying machine r U-B ix15
50MRJ (manufactured by Konica Corporation) and a live copy test was carried out, and a clear copy image was obtained that was faithful to the original image, had high contrast, excellent gradation, and quality. Even after repeating this process 5,000 times, a copy image as good as the initial one was obtained.

この感光体の初期特性は■い一−1230v、 EIA
−3(iQux−see、 V *=  10vであっ
た。これを電子写真複写機r U  B ix1550
M RJ (コニカ株式会社製)に装着し実写テストを
行い5000回繰返しても初期と変わらない良好な複写
画像を得た。
The initial characteristics of this photoreceptor are ■I-1230V, EIA
-3 (iQux-see, V * = 10v.
A photocopying test was carried out by attaching the copying machine to an M RJ (manufactured by Konica Corporation), and even after repeating it 5000 times, a copy image as good as the initial copy was obtained.

実施例8 本発明に係るピラジン誘導体は、半導体レーザプリンタ
用の感光体のキャリア輸送物質としても、特に優れた性
能を有する。実際に、以下のごとく半導体レーザ用感光
体を作成し、良好な結果を得lこ 。
Example 8 The pyrazine derivative according to the present invention has particularly excellent performance as a carrier transport material for a photoreceptor for a semiconductor laser printer. In fact, we produced a photoreceptor for a semiconductor laser as shown below and obtained good results.

導電性支持体としての外径10cmのアルミドラム上に
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−IU(I水化学社製)より成る厚さ0.
05μlの中間層を設け、その上に前記化合物(クロル
ダイアンブルー)2gを1.2−ジクロルエタン110
+a(lに混合し、ボールミルで24μl間分散した分
散液を乾燥後の膜厚が0.1.umになるようにして塗
布し、キャリア発生層を形成した。このキャリア発生層
の上に、例示化合物B−4,6gとメタクリル樹脂「ア
クリベット」(三菱レイヨン社製) logとを1.2
−ジクロルエタン70jnQに溶解した溶液を、乾燥後
の膜厚が18μmになるように塗布してキャリア輸送層
を形成し、本発明の電子写真感光体を作成した。
On an aluminum drum with an outer diameter of 10 cm as a conductive support, a 0.0 mm thick film made of vinyl chloride-vinyl acetate-maleic anhydride copolymer "S-LEC MF-IU (manufactured by I-Sui Kagaku Co., Ltd.)" was placed on an aluminum drum with an outer diameter of 10 cm as a conductive support.
05 μl of intermediate layer was provided, and 2 g of the above compound (chlordian blue) was added on top of 110 μl of 1,2-dichloroethane.
A carrier-generating layer was formed by coating a dispersion solution mixed with +a(l) and dispersed in 24 μl using a ball mill so that the film thickness after drying was 0.1 μm.On this carrier-generating layer, Exemplary compound B-4.6g and methacrylic resin "Acrivet" (manufactured by Mitsubishi Rayon Co., Ltd.) log is 1.2
- A solution dissolved in dichloroethane 70jnQ was applied so that the film thickness after drying was 18 μm to form a carrier transport layer, thereby producing an electrophotographic photoreceptor of the present invention.

この本発明の感光体表面でのレーザ光強度が0−85m
Wとなる半導体レーザ(790nm)を装着した実験機
により実写テストを行った。
The laser beam intensity on the surface of the photoreceptor of the present invention is 0-85 m.
A live photo test was conducted using an experimental machine equipped with a W semiconductor laser (790 nm).

感光体の表面を一6KVに帯電した後、レーザ光露光し
一250vのバイアス電圧で反転現像したところ、カブ
リのない良好な画像が得られた。
After the surface of the photoreceptor was charged to -6 KV, it was exposed to laser light and reverse development was performed at a bias voltage of -250 V, and a good image without fog was obtained.

比較例3 実施例8において例示化合物B−4に代えて下記の例示
化合物T−3を用いた他は同様にして比較用感光体を得
た。
Comparative Example 3 A comparative photoreceptor was obtained in the same manner as in Example 8, except that the following Exemplified Compound T-3 was used in place of Exemplified Compound B-4.

この比較用感光体を用いて実施例8と同様に半導体レー
ザによる実写テストを行ったがカブリが多く良好な画像
は得られなかった。
Using this comparative photoreceptor, a photo-taking test using a semiconductor laser was conducted in the same manner as in Example 8, but there was a lot of fog and good images could not be obtained.

〔発明の効果〕〔Effect of the invention〕

本発明により、高感度かつ反復使用の際の特性が極めて
安定であり、毒性の問題もない優れた感光体を得ること
ができる。
According to the present invention, it is possible to obtain an excellent photoreceptor that has high sensitivity, extremely stable characteristics during repeated use, and has no toxicity problem.

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

第1図〜第6図はそれぞれ本発明の電子写真感光体の機
械的構成例について示す断面図を表す。 ■・・・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 第1図 第2図 第5図 第6図
1 to 6 are sectional views showing examples of the mechanical structure of the electrophotographic photoreceptor of the present invention, respectively. ■... 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 substances Figure 1 Figure 2 Figure 5 Figure 6

Claims (4)

【特許請求の範囲】[Claims] (1)導電性支持体上に下記一般式〔 I 〕で表される
化合物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▼ 〔式中、Pzは▲数式、化学式、表等があります▼又は
▲数式、化学式、表等があります▼を表す。 R_1、R_2、R_3及びR_4は置換基を有してい
いてもよいアルキル基、アリール基を表す。〕
(1) An electrophotographic photoreceptor characterized by having a photosensitive layer containing a compound represented by the following general formula [I] on a conductive support. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, Pz represents ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. R_1, R_2, R_3 and R_4 represent an alkyl group or an aryl group which may have a substituent. ]
(2)上記一般式〔 I 〕中のR_1、R_2、R_3
及びR_4が全て同一の置換基であることを特徴とする
請求項1に記載の電子写真感光体。
(2) R_1, R_2, R_3 in the above general formula [I]
The electrophotographic photoreceptor according to claim 1, wherein all of R_4 and R_4 are the same substituent.
(3)前記感光層がキャリア発生物質とキャリア輸送物
質を含有し、該キャリア輸送物質として前記一般式〔
I 〕で表される化合物を用いる請求項1又は2に記載の
電子写真感光体。
(3) The photosensitive layer contains a carrier-generating substance and a carrier-transporting substance, and the carrier-transporting substance has the general formula [
The electrophotographic photoreceptor according to claim 1 or 2, which uses a compound represented by I].
(4)前記感光層がキャリア発生物質を含有するキャリ
ア発生層とキャリア輸送物質を含有するキャリア輸送層
の積層構成である請求項1、2又は3のいづれかに記載
の電子写真感光体。
(4) The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer has a laminated structure of a carrier generation layer containing a carrier generation substance and a carrier transport layer containing a carrier transport substance.
JP22400788A 1988-09-07 1988-09-07 Electrophogoraphic sensitive body Pending JPH0272370A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP22400788A JPH0272370A (en) 1988-09-07 1988-09-07 Electrophogoraphic sensitive body

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP22400788A JPH0272370A (en) 1988-09-07 1988-09-07 Electrophogoraphic sensitive body

Publications (1)

Publication Number Publication Date
JPH0272370A true JPH0272370A (en) 1990-03-12

Family

ID=16807129

Family Applications (1)

Application Number Title Priority Date Filing Date
JP22400788A Pending JPH0272370A (en) 1988-09-07 1988-09-07 Electrophogoraphic sensitive body

Country Status (1)

Country Link
JP (1) JPH0272370A (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04304465A (en) * 1991-04-02 1992-10-27 Fuji Electric Co Ltd Electrophotographic sensitive body
EP0578528A2 (en) * 1992-06-25 1994-01-12 Canon Kabushiki Kaisha Electrophotographic photosensitive member, and electrophotographic apparatus employing the same
US5393860A (en) * 1994-02-04 1995-02-28 Hoechst Celanese Corporation Polymer compositions containing substituted pyrazines
EP0926216A1 (en) * 1997-12-01 1999-06-30 Chisso Corporation Organic electroluminescent device using a triarylamine derivative
JP2007197426A (en) * 2005-12-28 2007-08-09 Semiconductor Energy Lab Co Ltd Pyrazine derivative, and light-emitting element, display and electronic device using the pyrazine derivative
JP2013526540A (en) * 2010-05-12 2013-06-24 バーテックス ファーマシューティカルズ インコーポレイテッド Compounds useful as ATR kinase inhibitors
US8920941B2 (en) 2005-12-28 2014-12-30 Semiconductor Energy Laboratory Co., Ltd. Pyrazine derivative, and light emitting element, display device, electronic device using the pyrazine derivative
US9263681B2 (en) 2012-12-10 2016-02-16 Nitto Denko Corporation Organic light emitting host materials
US9614162B2 (en) 2012-12-17 2017-04-04 Nitto Denko Corporation Light-emitting devices comprising emissive layer
US9630956B2 (en) 2010-05-12 2017-04-25 Vertex Pharmaceuticals Incorporated Compounds useful as inhibitors of ATR kinase
US9701674B2 (en) 2008-12-19 2017-07-11 Vertex Pharmaceuticals Incorporated Substituted pyrazines as ATR kinase inhibitors
US9791456B2 (en) 2012-10-04 2017-10-17 Vertex Pharmaceuticals Incorporated Method for measuring ATR inhibition mediated increases in DNA damage
US9862709B2 (en) 2011-09-30 2018-01-09 Vertex Pharmaceuticals Incorporated Processes for making compounds useful as inhibitors of ATR kinase
US10478430B2 (en) 2012-04-05 2019-11-19 Vertex Pharmaceuticals Incorporated Compounds useful as inhibitors of ATR kinase and combination therapies thereof
US11464774B2 (en) 2015-09-30 2022-10-11 Vertex Pharmaceuticals Incorporated Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62201446A (en) * 1986-02-28 1987-09-05 Canon Inc Electrophotographic sensitive body

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62201446A (en) * 1986-02-28 1987-09-05 Canon Inc Electrophotographic sensitive body

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04304465A (en) * 1991-04-02 1992-10-27 Fuji Electric Co Ltd Electrophotographic sensitive body
EP0578528A2 (en) * 1992-06-25 1994-01-12 Canon Kabushiki Kaisha Electrophotographic photosensitive member, and electrophotographic apparatus employing the same
EP0578528A3 (en) * 1992-06-25 1994-10-12 Canon Kk Electrophotographic photosensitive member, and electrophotographic apparatus employing the same.
US5393860A (en) * 1994-02-04 1995-02-28 Hoechst Celanese Corporation Polymer compositions containing substituted pyrazines
EP0926216A1 (en) * 1997-12-01 1999-06-30 Chisso Corporation Organic electroluminescent device using a triarylamine derivative
US9324951B2 (en) 2005-12-28 2016-04-26 Semiconductor Energy Laboratory Co., Ltd. Pyrazine derivative, and light emitting element, display device, electronic device using the pyrazine derivative
US8920941B2 (en) 2005-12-28 2014-12-30 Semiconductor Energy Laboratory Co., Ltd. Pyrazine derivative, and light emitting element, display device, electronic device using the pyrazine derivative
JP2007197426A (en) * 2005-12-28 2007-08-09 Semiconductor Energy Lab Co Ltd Pyrazine derivative, and light-emitting element, display and electronic device using the pyrazine derivative
US10961232B2 (en) 2008-12-19 2021-03-30 Vertex Pharmaceuticals Incorporated Substituted pyrazines as ATR kinase inhibitors
US10479784B2 (en) 2008-12-19 2019-11-19 Vertex Pharmaceuticals Incorporated Substituted pyrazin-2-amines as inhibitors of ATR kinase
US9701674B2 (en) 2008-12-19 2017-07-11 Vertex Pharmaceuticals Incorporated Substituted pyrazines as ATR kinase inhibitors
JP2013526540A (en) * 2010-05-12 2013-06-24 バーテックス ファーマシューティカルズ インコーポレイテッド Compounds useful as ATR kinase inhibitors
US9630956B2 (en) 2010-05-12 2017-04-25 Vertex Pharmaceuticals Incorporated Compounds useful as inhibitors of ATR kinase
US10208027B2 (en) 2011-09-30 2019-02-19 Vertex Pharmaceuticals Incorporated Processes for preparing ATR inhibitors
US9862709B2 (en) 2011-09-30 2018-01-09 Vertex Pharmaceuticals Incorporated Processes for making compounds useful as inhibitors of ATR kinase
US10822331B2 (en) 2011-09-30 2020-11-03 Vertex Pharmaceuticals Incorporated Processes for preparing ATR inhibitors
US10478430B2 (en) 2012-04-05 2019-11-19 Vertex Pharmaceuticals Incorporated Compounds useful as inhibitors of ATR kinase and combination therapies thereof
US11110086B2 (en) 2012-04-05 2021-09-07 Vertex Pharmaceuticals Incorporated Compounds useful as inhibitors of ATR kinase and combination therapies thereof
US9791456B2 (en) 2012-10-04 2017-10-17 Vertex Pharmaceuticals Incorporated Method for measuring ATR inhibition mediated increases in DNA damage
US9263681B2 (en) 2012-12-10 2016-02-16 Nitto Denko Corporation Organic light emitting host materials
US9614162B2 (en) 2012-12-17 2017-04-04 Nitto Denko Corporation Light-emitting devices comprising emissive layer
US11464774B2 (en) 2015-09-30 2022-10-11 Vertex Pharmaceuticals Incorporated Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors

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