JPS59127046A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPS59127046A
JPS59127046A JP230783A JP230783A JPS59127046A JP S59127046 A JPS59127046 A JP S59127046A JP 230783 A JP230783 A JP 230783A JP 230783 A JP230783 A JP 230783A JP S59127046 A JPS59127046 A JP S59127046A
Authority
JP
Japan
Prior art keywords
intermediate layer
ring
pigment
insulating resin
org
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
JP230783A
Other languages
Japanese (ja)
Inventor
Masaomi Sasaki
正臣 佐々木
Mitsuru Seto
瀬戸 満
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.)
Ricoh Co Ltd
Original Assignee
Ricoh 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 Ricoh Co Ltd filed Critical Ricoh Co Ltd
Priority to JP230783A priority Critical patent/JPS59127046A/en
Publication of JPS59127046A publication Critical patent/JPS59127046A/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
    • G03G5/0664Dyes
    • G03G5/0675Azo dyes
    • G03G5/0679Disazo dyes
    • G03G5/0683Disazo dyes containing polymethine or anthraquinone groups

Landscapes

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

Abstract

PURPOSE:To improve the electrical characteristics of an electrophotographic sensitive body obtd. by successively forming an intermediate layer contg. fine particles of an org. pigment dispersed in an insulating resin and a photoconductive layer of an Se compound on an electrically conductive support by using a specified disazo pigment as the org. pigment. CONSTITUTION:An intermediate layer contg. fine particles of an org. pigment dispersed in an insulating resin and a photoconductive layer of an Se compound are successively formed on an electrically conductive support. At this time, a disazo pigment represented by formula I [where A is a group represented by formula II or III (where each of X, Ar1 and Ar2 is a benzene ring or the like, R1 is H, lower alkyl or the like, and R2 is lower alkyl or the like)] is used as the org. pigment. The electrically conductive support is made of a metal such as Al or Ni, the oxide thereof, synthetic paper coated with the metal or metallic oxide, or the like. Since the intermediate layer consists essentially of the insulating resin and the disazo pigment represented by the formula I , the adhesive property of the photoconductive layer to the support and the electrical characteristics are improved.

Description

【発明の詳細な説明】 本発明は支持体とセレン系光導電層との間に光導電性中
間層を有する電子写真感光体に関する。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor having a photoconductive intermediate layer between a support and a selenium-based photoconductive layer.

導電性支持体上に、絶縁性樹脂結着剤中に分散質として
無機又は有機微粒子を分散した中間真感光体が知られて
いる。このような層構造からなる電子写真感光体におい
て中間層の目的は支持体と光導電層間の接着性向上及び
電気特性の向上である。中間層は結着剤中に分散する粒
子の種類によって一般に低抵抗中間層及び光導電性中間
層の2種に大別される。前者の例としては分散質として
カーメンを用いたもの(%開昭49−126339号公
報)や金属又はカルコゲン化合物を用いたもの(%公昭
54−36859号公報)があり、−また後者の例とし
てはフタロシアニンを用いたもの(特公昭44−x26
71号公報ンがある。しかし前者の中間層では分散条件
によっては感光体の帯電特性、残留電位等の電気特性が
大きく変動する。従って分散条件の制御が課題である。
Intermediate photoreceptors are known in which fine inorganic or organic particles are dispersed as dispersoids in an insulating resin binder on a conductive support. In an electrophotographic photoreceptor having such a layered structure, the purpose of the intermediate layer is to improve the adhesiveness between the support and the photoconductive layer and to improve the electrical properties. Interlayers are generally classified into two types, low resistance interlayers and photoconductive interlayers, depending on the type of particles dispersed in the binder. Examples of the former include those using carmen as a dispersoid (% Publication No. 49-126339) and those using metals or chalcogen compounds (Japanese Publication No. 54-36859); is one using phthalocyanine (Special Publication No. 44-x26
There is a publication No. 71. However, in the former intermediate layer, electrical properties such as charging properties and residual potential of the photoreceptor vary greatly depending on dispersion conditions. Therefore, controlling the dispersion conditions is a challenge.

一方、後者の中間層でも分散質が7タロシアニン顔料で
ある場合、電気特性、特に残留電位が繰返し使用時に変
動するという欠点がある。なお上記区分には属さないそ
の他の中間層として分散質を用いずに非結晶性樹脂単独
よりなるもの(特開昭!53−103742号公報)が
知られているが、この中間層の目的はその上に設けられ
た光導電層における結晶化抑制効果を意図したもので、
上記2種の中間層とは異なっている。
On the other hand, when the dispersoid in the latter intermediate layer is a 7-talocyanine pigment, there is a drawback that the electrical properties, particularly the residual potential, fluctuate during repeated use. Note that another intermediate layer that does not fall into the above category is known to be made of an amorphous resin alone without using a dispersoid (Japanese Patent Application Laid-Open No. 53-103742), but the purpose of this intermediate layer is to This is intended to suppress crystallization in the photoconductive layer provided on top of the photoconductive layer.
This is different from the above two types of intermediate layers.

本発明の目的は中間層に用いられる分散粒子の分散条件
や繰返し使用においても電気特性が安定で、しかも中間
層による増感効果、結晶化抑制効果及び接着性向上によ
る可撓性向上効果を併せ持つ上、優れた電子写真特性を
肴1、る電子写真感光体を提供することである。
The object of the present invention is to ensure that the electrical properties of the dispersed particles used in the intermediate layer are stable even under the dispersion conditions and repeated use, and that the intermediate layer also has a sensitizing effect, a crystallization suppressing effect, and an effect of improving flexibility by improving adhesiveness. Another object of the present invention is to provide an electrophotographic photoreceptor having excellent electrophotographic properties.

即ち、本発明は導電性支持体上に、有機顔料の微細粒子
を絶縁性樹脂中に分散せしめ【なる中間層と更にその上
にセレン、セレン合金又はセレン化合物よりなる光導電
層とを設げた電子写真感光体において、前記有機顔料が
一般式(ここでXはベンゼン環、ナフタレン環などの芳
香環、インドール環、カルノ々ゾール環。
That is, the present invention provides an intermediate layer in which fine particles of an organic pigment are dispersed in an insulating resin on a conductive support, and a photoconductive layer made of selenium, a selenium alloy, or a selenium compound thereon. In the electrophotographic photoreceptor, the organic pigment has a general formula (where X is an aromatic ring such as a benzene ring or a naphthalene ring, an indole ring, or a carnozole ring.

ベンゾフラン環なとのへテロ環又はそれらの置換体、 
Arlは4ンゼン環、ナフタレン環などの芳香環、ジベ
ンゾフランなどのへテロ環又はそれらの置換体、Arl
はベンゼン環、ナフタレン環などの芳香環又はそれらの
置換体、R1は水素、低級アルキル基、フェニル基又は
その置換体、−は低級アルキル基、カルIキシル基又は
そのエステル)を表わす。〕 で示されるジスアゾ顔料であることを特徴とするもので
ある。
Heterocycles such as benzofuran rings or substituted products thereof,
Arl is an aromatic ring such as a tetrabenzene ring or a naphthalene ring, a heterocyclic ring such as dibenzofuran, or a substituted product thereof;
represents an aromatic ring such as a benzene ring or a naphthalene ring, or a substituted product thereof; R1 represents hydrogen, a lower alkyl group, a phenyl group, or a substituted product thereof; - represents a lower alkyl group, a carbyl group, or an ester thereof; ] It is characterized by being a disazo pigment shown in the following.

Xの芳香環またはへテロ環における置換基としてはハロ
ゲンが、Arlにおける芳香環またはへテロ環における
置換基としてはノ・ロゲン、低級アルキル基、低級アル
コキシ基、低級ジアルキルアミノ基、ニトロ基、シアノ
基、カルIキシル基、スルホン酸基又はその塩などが挙
げられる。Arcの芳香環における置換基とし【はAy
lにおける置換基のほか、アシルアミノ基などが挙げら
れる。またR8のフェニル基における置換基としてはノ
10ゲンが挙げられる。
The substituent on the aromatic ring or heterocycle of group, Cal I xyl group, sulfonic acid group, or a salt thereof. As a substituent in the aromatic ring of Arc, [is Ay
In addition to the substituents in l, examples include an acylamino group. Further, examples of the substituent on the phenyl group of R8 include 10gen.

本発明はこのように導電性支持体、中間層及び光導電層
を有する電子写真感光体の中間層における分散質として
前記一般式で示されるジスアゾ顔料を用いたものである
The present invention uses the disazo pigment represented by the above general formula as a dispersoid in the intermediate layer of an electrophotographic photoreceptor having a conductive support, an intermediate layer, and a photoconductive layer.

導電性支持体としては例えばAn、Ni、ステンレスス
チール等の金属又は金属酸化物よりな゛る板;An、P
d、Au等の金属をコートした合成紙、ゾツスチックフ
イルム等の絶縁性シート;高分子4級アンモニウム塩、
ポリスチレンスルホン酸塩等の導電性物質を含浸した紙
又は布等が使用される。
Examples of conductive supports include plates made of metals or metal oxides such as An, Ni, and stainless steel; An, P;
d, insulating sheets such as synthetic paper coated with metals such as Au, and zotstic films; polymeric quaternary ammonium salts;
Paper or cloth impregnated with a conductive substance such as polystyrene sulfonate is used.

中間層は絶縁性樹脂及び前記一般式のジスアゾ顔料を主
成分として構成される。絶縁性樹脂としては例えばエポ
キシ樹脂、アクリル樹脂、ポリイミド、ポリアミド、ブ
チ2−ル樹脂、ポリエステル等が挙げられるが、中でも
ポリエステル及びゾチラール樹脂は特に良好な結果を与
える。またこれら樹脂の固有の特性を補なう目的で2種
以上の絶縁性樹脂を用いることも可能である。一方、ジ
スアゾ顔料の具体例としては下記のものが挙げられる。
The intermediate layer is mainly composed of an insulating resin and a disazo pigment of the above general formula. Examples of the insulating resin include epoxy resin, acrylic resin, polyimide, polyamide, butyl resin, polyester, etc. Among them, polyester and zotyral resin give particularly good results. It is also possible to use two or more types of insulating resins for the purpose of supplementing the unique characteristics of these resins. On the other hand, specific examples of disazo pigments include the following.

以上の様なジスアゾ顔料は公知の方法に従って、例えば
特開昭56−9753号公報記載の方法に準じて容易に
得ることができる。
The above-mentioned disazo pigments can be easily obtained according to known methods, for example, according to the method described in JP-A-56-9753.

こうして得られるジスアゾ顔料の絶縁性樹脂への分散量
は1〜50重量%が適当である。分散量が前記範囲より
多過ぎると、接着性が低下し、その結果、可撓性向上効
果が損なわれ、また少な過ぎると、残留電位の増加を招
く。中間層の厚さは5μ以下が適当で、好ましくは1〜
3μである。なお本発明1中間層には以上の2成分の他
、各種特性の向上及び安定化を計るために、他の分散質
を添加してもよい。
The amount of the thus obtained disazo pigment dispersed in the insulating resin is suitably 1 to 50% by weight. If the amount of dispersion is too large than the above range, the adhesion will decrease, resulting in a loss of flexibility improvement effect, and if it is too small, the residual potential will increase. The thickness of the intermediate layer is suitably 5 μ or less, preferably 1 to 5 μm.
It is 3μ. In addition to the above two components, other dispersoids may be added to the intermediate layer of the present invention 1 in order to improve and stabilize various properties.

光導電層はセレン、セレン合金又はセレン化合物から構
成される。セレン合金又はセレン化合物としては5eT
e yAsl Se318 e  B 1合金、86−
sb合金等が挙げられる。光導電層の厚さは100μ以
下が適当で、好ましくは10〜70μである。
The photoconductive layer is composed of selenium, a selenium alloy, or a selenium compound. 5eT as a selenium alloy or selenium compound
e yAsl Se318 e B 1 alloy, 86-
Examples include sb alloy. The thickness of the photoconductive layer is suitably 100 microns or less, preferably 10 to 70 microns.

本発明の感光体を作るには導電性支持体上に前記ジスア
ゾ顔料を分散した絶縁性樹脂溶液を塗布乾燥して中間層
を形成し、その上にセレン、セレン合金又はセレン化合
物を蒸着して光導電層を形成すればよい。
To make the photoreceptor of the present invention, an insulating resin solution in which the disazo pigment is dispersed is coated on a conductive support and dried to form an intermediate layer, and selenium, a selenium alloy, or a selenium compound is deposited on the intermediate layer. A photoconductive layer may be formed.

以下に本発明を実施例によって説明する。The present invention will be explained below by way of examples.

実施例1 ブチ2−ル樹脂(ユニオンカーバイト社製XYHL)4
重量部をガラスポット中でナト2ヒドロフ2フ11重量
部に溶解し、ついでこの中に化合物ムlのジスアゾ顔料
1重量部及びステンレススチールゼールを加え、72時
間ミリングした。得られた分散液にナト2ヒドロフ2フ
34重量部を加え、中間層形成液を調製、した。
Example 1 Butylene resin (XYHL manufactured by Union Carbide) 4
Part by weight was dissolved in 11 parts by weight of sodium hydroxide in a glass pot, and then 1 part by weight of the disazo pigment of Compound Mul and stainless steel Zeel were added thereto and milled for 72 hours. 34 parts by weight of Nato2HydroF2F was added to the obtained dispersion to prepare an intermediate layer forming liquid.

次にこの液をステンレススチール(5US304)製支
持体上に乾燥後の厚さがlμになるよう塗布し、100
℃で1時間乾燥して中間層を形成し、更にその上にセレ
ンを真空蒸着して厚さ60μの無定形セレンよりなる光
導電層を形成することにより、電子写真感光体を作製 
゛した。
Next, this solution was applied onto a support made of stainless steel (5US304) so that the thickness after drying was lμ.
An electrophotographic photoreceptor was prepared by drying at ℃ for 1 hour to form an intermediate layer, and then vacuum-depositing selenium thereon to form a photoconductive layer made of amorphous selenium with a thickness of 60 μm.
I did.

比較のため、中間層形成液とし【前記ブチラール樹脂1
重量部をテトラヒドロフラン9重量部に溶解した溶液を
用いた他は同様にして電子写真感光体を、作製した。
For comparison, the intermediate layer forming liquid [butyral resin 1]
An electrophotographic photoreceptor was produced in the same manner except that a solution in which parts by weight were dissolved in 9 parts by weight of tetrahydrofuran was used.

次に以上の2種の感光体について電子写真特性をテスト
し、下表の結果を得た。
Next, the above two types of photoreceptors were tested for electrophotographic characteristics, and the results shown in the table below were obtained.

注)vM=サンプル表面に5KVのコロナ放電を20秒
間行なった時の表面電位。
Note: vM = surface potential when a 5KV corona discharge is applied to the sample surface for 20 seconds.

D−D : VO/VMの値(Voは20秒間暗減衰さ
せた時の表面電位)。
DD: VO/VM value (Vo is the surface potential when dark decayed for 20 seconds).

E凭:暗減衰の後、タングステンランプにより表面照度
が20.8uxになるよう光照射し、表面電位がVOの
強にな るに要する露光量。
E: After dark decay, light is irradiated with a tungsten lamp so that the surface illuminance becomes 20.8 ux, and the amount of exposure required for the surface potential to become strong VO.

■R:光照射を20秒間行なった後の表面電位。■R: Surface potential after 20 seconds of light irradiation.

この表から判るように本発明の感光体におけるジスアゾ
顔料を分散した中間層の効果は明らかで、特に残留電位
の低下に著しい効果が認められる。
As can be seen from this table, the effect of the intermediate layer in which the disazo pigment is dispersed in the photoreceptor of the present invention is clear, and in particular, a remarkable effect is observed in reducing the residual potential.

実施例2 ポリエステル(デュポン社製ポリエステルアドヘシブ)
9重量部をガラスポット中でテトラヒドロフラン23重
量部に溶解し、この中に化合物7i1のジスアゾ顔料1
重量部及び実施例1と同じステンレススチールI−ルを
加えて72時間ミリングした。得られた分散液に更にテ
トラヒドロフラン63重量部を加えて中間層形成液を調
製した。次にこの液を実施例1と同じ支持体上に乾燥後
の厚さが3μとなるよう塗布し、100℃で1時間乾燥
して中間層を形成し、更にその上にTe含有i8重量%
のS・−Te合金を真空蒸着し【厚さ60μの非晶質S
s −Toよりなる光導電層を形成することにより電子
写真感光体を作製した。
Example 2 Polyester (Polyester Adhesive manufactured by DuPont)
Disazo pigment 1 of compound 7i1 was dissolved in 23 parts by weight of tetrahydrofuran in a glass pot.
Parts by weight and the same stainless steel I-ru as in Example 1 were added and milled for 72 hours. Further, 63 parts by weight of tetrahydrofuran was added to the obtained dispersion to prepare an intermediate layer forming liquid. Next, this solution was coated on the same support as in Example 1 so that the thickness after drying was 3μ, and dried at 100°C for 1 hour to form an intermediate layer.
vacuum evaporated S/-Te alloy [60μ thick amorphous S]
An electrophotographic photoreceptor was produced by forming a photoconductive layer made of s-To.

比較のため中間層形成液中の前記ジスアゾ顔料の代りに
β−銅7タロシアニンを用いた他は同様にして電子写真
感光体を作製した。
For comparison, an electrophotographic photoreceptor was prepared in the same manner except that β-copper 7-talocyanine was used instead of the disazo pigment in the intermediate layer forming solution.

次にこれら感光体を市販の電子写真複写機にセットし、
繰返し使用テストを行なったところ、比較品では初期の
残留電位20Vが110Vと約90V増加したのに対し
、本発明品では残留電位の変動は見られなかった。
Next, these photoreceptors are set in a commercially available electrophotographic copying machine,
When a repeated use test was conducted, the initial residual potential of 20V increased by approximately 90V to 110V in the comparison product, whereas no fluctuation in the residual potential was observed in the product of the present invention.

Claims (1)

【特許請求の範囲】 1、 導電性支持体上に、有機顔料の微細粒子を絶縁性
樹脂中に分散せしめてなる中間層と更にその上にセレン
、セレン合金又はセレン化金物よりなる光導電層とを設
けた電子写真感光体において、前記有機顔料が一般式 (ここでXはベンゼン環、ナフタレン環などの芳香環、
インドール環、カル、1ゾール環、ベンゾフラン環なと
のへテロ環又はそれらの置換体、Ar1はベンゼン環、
ナフタレン環などの芳香環、ジベンゾフランなどのへテ
ロ環又はそれらの置換体、Arck!ベンゼン環、ナフ
タレン環などの芳香環X41それらの置換体、R1は水
素、低級アルキル基、フェニル基又はその置換体、Rm
&ま低級アルキル基、カルメキシル基又はそのエステル
)を表わす。〕 で示されるジスアゾ顔料であることを特徴とする電子写
真感光体。
[Scope of Claims] 1. An intermediate layer formed by dispersing fine particles of an organic pigment in an insulating resin on a conductive support, and further thereon a photoconductive layer formed of selenium, a selenium alloy, or a metal selenide. In the electrophotographic photoreceptor provided with
A hetero ring with an indole ring, car, 1 zole ring, benzofuran ring, or a substituted product thereof, Ar1 is a benzene ring,
Aromatic rings such as naphthalene rings, hetero rings such as dibenzofuran, or substituted products thereof, Arck! Aromatic rings such as benzene ring and naphthalene ring
& represents a lower alkyl group, carmexyl group, or an ester thereof). ] An electrophotographic photoreceptor characterized by being a disazo pigment represented by the following.
JP230783A 1983-01-12 1983-01-12 Electrophotographic sensitive body Pending JPS59127046A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP230783A JPS59127046A (en) 1983-01-12 1983-01-12 Electrophotographic sensitive body

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP230783A JPS59127046A (en) 1983-01-12 1983-01-12 Electrophotographic sensitive body

Publications (1)

Publication Number Publication Date
JPS59127046A true JPS59127046A (en) 1984-07-21

Family

ID=11525696

Family Applications (1)

Application Number Title Priority Date Filing Date
JP230783A Pending JPS59127046A (en) 1983-01-12 1983-01-12 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPS59127046A (en)

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