JPH01293349A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPH01293349A
JPH01293349A JP12309588A JP12309588A JPH01293349A JP H01293349 A JPH01293349 A JP H01293349A JP 12309588 A JP12309588 A JP 12309588A JP 12309588 A JP12309588 A JP 12309588A JP H01293349 A JPH01293349 A JP H01293349A
Authority
JP
Japan
Prior art keywords
sensitivity
electrophotographic
transfer layer
charge transfer
organic
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
JP12309588A
Other languages
Japanese (ja)
Other versions
JP2657300B2 (en
Inventor
Masaya Fujino
藤野 正家
Nobuo Matsumoto
信雄 松本
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.)
Nippon Telegraph and Telephone Corp
Original Assignee
Nippon Telegraph and Telephone Corp
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 Telegraph and Telephone Corp filed Critical Nippon Telegraph and Telephone Corp
Priority to JP12309588A priority Critical patent/JP2657300B2/en
Publication of JPH01293349A publication Critical patent/JPH01293349A/en
Application granted granted Critical
Publication of JP2657300B2 publication Critical patent/JP2657300B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related 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
    • G03G5/043Photoconductive layers characterised by having two or more layers or characterised by their composite structure
    • G03G5/047Photoconductive layers characterised by having two or more layers or characterised by their composite structure characterised by the charge-generation layers or charge transport layers
    • 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
    • G03G5/05Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528Macromolecular bonding materials
    • G03G5/0557Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
    • G03G5/0578Polycondensates comprising silicon atoms in the main chain
    • 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
    • G03G5/07Polymeric photoconductive materials
    • G03G5/078Polymeric photoconductive materials comprising silicon atoms

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

PURPOSE:To enhance sensitivity and to prevent environmental pollution by forming an electric charge transfer layer made of a polymer composed of a main silicon chain and alkylated aryl side chains. CONSTITUTION:A charge generating layer is made of an inorganic photoconductor, such as amorphous selenium, or an organic photoconductive film obtained by dispersing an organic pigment into a binder resin or vapor depositing the pigment, and the charge transfer layer made of the polymer composed of the main silicon chain and the alkylated aryl side chains, thus permitting charge carrier mobility and carrier injection efficiency both being sensitivity governing factors to be enhanced and environmental pollution to be prevented.

Description

【発明の詳細な説明】 〔発明の産業上利用分野〕 本発明は電子写真感光体、さらに詳細には電荷発生層と
電荷移動層からなる二層式電子写真感光体に関するもの
である。
DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field of the Invention] The present invention relates to an electrophotographic photoreceptor, and more particularly to a two-layer electrophotographic photoreceptor comprising a charge generation layer and a charge transfer layer.

〔従来技術] 電子写真感光体としては、これまでアモルファスセレン
等のセレン系が主として用いられてきたが、有毒である
ことや焼却処分が困難である等の問題があるため、有機
化合物を代替材料として用いることが検討されている。
[Prior Art] Until now, selenium-based materials such as amorphous selenium have been mainly used for electrophotographic photoreceptors, but because of problems such as being toxic and difficult to dispose of by incineration, organic compounds have been used as alternative materials. It is being considered for use as a

特に、高感度化の観点から、光照射により電荷を発生す
る電荷発生層(CGL)と、発生した電荷を輸送する電
荷移動層(CTL)からなる積層式が主流となっている
In particular, from the viewpoint of increasing sensitivity, a laminated type consisting of a charge generation layer (CGL) that generates charges by light irradiation and a charge transfer layer (CTL) that transports the generated charges has become mainstream.

このような積層式電子写真感光体においては、CTLに
おけるドリフト移動度の大きさが感度を支配する因子の
一つであり、ドリフト移動度が大きいほど感度が高い。
In such a laminated electrophotographic photoreceptor, the magnitude of the drift mobility in the CTL is one of the factors governing the sensitivity, and the greater the drift mobility, the higher the sensitivity.

最近、主鎖がケイ素からなり、側鎖の一部がフェニル基
からなる有機ポリシランがこれまでの有機光電導体より
も大きなドリフト移動度を持つことが報告され(例えば
、M、ストルカ他(M、 5tolka et al、
 )、ジャーナル オンボリマー サイエンス:ポリマ
ー ケミストリー、25@、823頁(1987年) 
 (J、 Polym。
Recently, it has been reported that organic polysilanes whose main chain is composed of silicon and whose side chains are partially composed of phenyl groups have higher drift mobility than conventional organic photoconductors (for example, M., Storka et al. 5tolka et al.
), Journal Onbolymer Science: Polymer Chemistry, 25@, p. 823 (1987)
(J, Polym.

Sci、:Polym、Chew、、 25 、823
 (1987)) 、この有機ポリシランをCTLとし
、アモルファスセレンをCGLとした電子写真感光体が
作製されている。
Sci,:Polym,Chew,, 25, 823
(1987)), an electrophotographic photoreceptor has been produced using this organic polysilane as CTL and amorphous selenium as CGL.

〔発明が解決する問題点] しかし、他の感度支配因子であるCGLからCTLへの
キャリア注入効率があまりよくない。この原因の一つは
、前述の有機ポリシランのバンドギャップが3.6eV
程度と大きいことである。
[Problems to be Solved by the Invention] However, the carrier injection efficiency from the CGL to the CTL, which is another factor governing sensitivity, is not very good. One of the reasons for this is that the band gap of the organic polysilane mentioned above is 3.6 eV.
It is a big thing.

しかし、最近、ジ(アルキル置換アリール)ポリシラン
のバンドギャップがこれまでの有機ポリシランに比べ、
小さいことが見出され、3.1eν程度の値が報告され
ている(R,D、  ミラー他(R,D、 Mille
r et al、) 、ジャーナル オン ポリマー 
サイエンス:ポリマー レターズ、25巻、321頁 
(1987年)  (J、 Polym、 Sci、:
Polym、 Lett、、 25.321 (198
7) ) 、そこで、このような狭バンドギャップの有
機ポリシランを用いれば、ドリフト移動度と注入効率の
両者を改善することができると考え、本発明に至った。
However, recently, the band gap of di(alkyl-substituted aryl)polysilanes has increased compared to conventional organic polysilanes.
It has been found that the value is small, and a value of about 3.1eν has been reported (R, D, Mille et al.
r et al.), Journal on Polymers
Science: Polymer Letters, Volume 25, Page 321
(1987) (J, Polym, Sci.:
Polym, Lett, 25.321 (198
7) ) Therefore, the present invention was developed based on the idea that both drift mobility and injection efficiency could be improved by using such a narrow bandgap organic polysilane.

本発明は上述の問題点に鑑みなされたものであり、高感
度で無公害な電子写真感光体を提供することにある。
The present invention has been made in view of the above-mentioned problems, and it is an object of the present invention to provide a highly sensitive and non-polluting electrophotographic photoreceptor.

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

上述の問題点を解決するため、本発明による電子写真感
光体は、電荷発生層と電荷移動層からなる二層式電子写
真感光体において、主鎖がケイ素の連鎖よりなり、側鎖
がアルキル置換アリール基よりなる高分子化合物で電荷
移動層を構成したことを特徴とするものである。
In order to solve the above-mentioned problems, an electrophotographic photoreceptor according to the present invention is a two-layer electrophotographic photoreceptor consisting of a charge generation layer and a charge transfer layer, in which the main chain is composed of a silicon chain and the side chain is alkyl-substituted. It is characterized in that the charge transfer layer is made of a polymer compound consisting of an aryl group.

本発明は、上述のようにCGLとCTLからなる二層式
電子写真感光体において、アモルファスセレン等の無機
光電導体や、有機顔料の樹脂分散膜あるいは蒸着膜等の
有機光電導体でCGLを構成し、主鎖がケイ素の連鎖よ
りなり、側鎖がアルキル置換アリール基よりなる高分子
化合物でCTLを構成することを最も主要な特徴とする
。感度支配因子であるキャリア移動度とキャリア注入効
率が改善されたことにより電子写真感光体の感度が向上
し、かつ、無公害化された点が従来の技術と異なる。
The present invention provides a two-layer electrophotographic photoreceptor consisting of a CGL and a CTL as described above, in which the CGL is composed of an inorganic photoconductor such as amorphous selenium, or an organic photoconductor such as a resin-dispersed film or a vapor-deposited film of an organic pigment. The most important feature is that CTL is composed of a polymer compound whose main chain consists of a silicon chain and whose side chain consists of an alkyl-substituted aryl group. This method differs from conventional technology in that the sensitivity of the electrophotographic photoreceptor is improved by improving carrier mobility and carrier injection efficiency, which are factors governing sensitivity, and that it is pollution-free.

前述の主鎖がケイ素の連鎖よりなり、側鎖がアルキル置
換アリール基よりなる高分子化合物としては、たとえば
下記の一般式で示される化合物を使用することができる
As the aforementioned polymer compound whose main chain consists of a silicon chain and whose side chain consists of an alkyl-substituted aryl group, for example, a compound represented by the following general formula can be used.

前記一般式中、Rは同じまたは異なるアルキル基であり
、ノーマルアルキル基のほか、イソプロピル、イソブチ
ルのように分岐したアルキル基であることもできる。R
の炭素数は、2〜20であるのが好ましい。炭素数が2
未満であると、有機溶媒に溶解しにくく、塗布などによ
って膜を形成しにくい恐れがあり、一方20を越えると
粘度が増して、作業性が劣り、また電子写真性を損なう
恐れを生じるからである。特に好ましくは、炭素数は4
〜12であるのがよい。
In the above general formula, R is the same or different alkyl group, and in addition to a normal alkyl group, it can also be a branched alkyl group such as isopropyl and isobutyl. R
The number of carbon atoms is preferably 2 to 20. Number of carbons is 2
If it is less than 20, it may be difficult to dissolve in organic solvents and it may be difficult to form a film by coating, etc. On the other hand, if it exceeds 20, the viscosity will increase, resulting in poor workability and the risk of impairing electrophotographic properties. be. Particularly preferably, the number of carbon atoms is 4.
~12 is preferable.

下記の実施例においては、−例として、CGLがアモル
ファスセレン、フタロシアニン系顔料、ビスアゾ顔料、
または、ペリレン顔料で構成され、CTLが下記の一般
式(1)および(2)で示されるジ(アルキルフェニル
)ポリシランで構成された電子写真感光体について説明
するが、本発明はこれらの実施例に限定されない。
In the following examples, CGL may be amorphous selenium, a phthalocyanine pigment, a bisazo pigment,
Alternatively, an electrophotographic photoreceptor composed of a perylene pigment and whose CTL is composed of a di(alkylphenyl)polysilane represented by the following general formulas (1) and (2) will be described. but not limited to.

(以下余白) C4H9C6H13 〔実施例1] セレンをlXl0−’torrの真空下でアルミ基盤上
に蒸着してCGL、(膜厚:0.3μm)とし、その上
にジ(ブチルフェニル)ポリシラン(1)をスピンコー
ティング法で塗布してCTL (膜厚:10μm)とし
た。ハロゲンランプ光を2Q luxの照度で照射し半
減露光量を測定して電子写真感度を評価した。一般式(
2)に示す他の高分子化合物でCTLを構成した試料も
同様にして作製し、電子写真感度を評価した。
(Left below) C4H9C6H13 [Example 1] Selenium is deposited on an aluminum substrate under a vacuum of 1X10-'torr to form CGL (film thickness: 0.3 μm), and di(butylphenyl)polysilane (1 ) was applied by spin coating to form CTL (film thickness: 10 μm). The electrophotographic sensitivity was evaluated by irradiating the film with halogen lamp light at an illuminance of 2Q lux and measuring the half-life exposure. General formula (
Samples in which CTLs were composed of other polymeric compounds shown in 2) were prepared in the same manner, and the electrophotographic sensitivity was evaluated.

〔実施例2〕 チタニルフタロシアニンをlXl0−’torrの真空
下でアルミ基盤上に蒸着してCGL (膜厚:0.3μ
m)とし、その上にジ(ブチルフェニル)ポリシラン(
1)をスピンコーティング法で塗布してCTL (膜厚
:10μm)とした。実施例1と同様にして電子写真感
度を評価した。一般式(2)に示す他の高分子化合物で
CTLを構成した試料も同様にして作製し、電子写真感
度を評価した。
[Example 2] CGL (film thickness: 0.3μ) was obtained by depositing titanyl phthalocyanine on an aluminum substrate under a vacuum of 1X10-'torr.
m) and di(butylphenyl)polysilane (
1) was applied by spin coating to form a CTL (film thickness: 10 μm). Electrophotographic sensitivity was evaluated in the same manner as in Example 1. Samples in which CTLs were composed of other polymer compounds represented by general formula (2) were prepared in the same manner, and the electrophotographic sensitivity was evaluated.

〔実施例3〕 ポリビニルブチラールにチタニルフタロシアニンを50
−t%分散した層をアルミ基盤上にワイヤバーコーティ
ング法で塗布してCGL (膜厚:0゜5μm)とし、
その上にジ(ブチルフェニル)ポリシラン(1)を塗布
してCTL(膜r!1.:10μm)とした。実施例1
と同様にして電子写真感度を評価した。一般式(2)に
示す他の高分子化合物でCTLを構成した試料も同様に
して作製し、電子写真感度を評価した。
[Example 3] 50% titanyl phthalocyanine in polyvinyl butyral
-t% dispersed layer is coated on an aluminum substrate by wire bar coating method to form CGL (film thickness: 0°5 μm),
Di(butylphenyl)polysilane (1) was applied thereon to form a CTL (film r!1.: 10 μm). Example 1
Electrophotographic sensitivity was evaluated in the same manner as above. Samples in which CTLs were composed of other polymer compounds represented by general formula (2) were prepared in the same manner, and the electrophotographic sensitivity was evaluated.

第1表に、今回作製した電子写真感光体の感度の評価結
果を示す。樹脂分散型のCGLにおいては、バインダー
樹脂をポリエステル等の他の高分子化合物を用いた場合
や、種々の打機ポリシランを用いた場合にもほぼ同様の
効果がTlTl LEされた。
Table 1 shows the evaluation results of the sensitivity of the electrophotographic photoreceptor produced this time. In resin-dispersed CGL, almost the same effects were obtained when other polymeric compounds such as polyester were used as the binder resin, and when various types of perforated polysilane were used.

以上の実施例における半減露光量は、これまで高感度と
されていたセレン系電子写真感光体と同等程度であり、
従来のを機系電子写真感光体よりも1桁程度高感度であ
る。
The half-decreased exposure amount in the above examples is comparable to that of selenium-based electrophotographic photoreceptors, which have been considered to have high sensitivity,
The sensitivity is about one order of magnitude higher than that of conventional electrophotographic photoreceptors.

なお、ビスアゾ顔料、ペリレン顔料としては、下記の一
般式(3)および(4)に示した顔料を使用した。
Incidentally, as the bisazo pigment and perylene pigment, pigments shown in the following general formulas (3) and (4) were used.

ビスアゾ原料 ペリレン顔料 (発明の効果) 以上説明したように、半減露光量で評価される電子写真
感度がこれまでのセレン系電子写真感光体と同等程度で
あり、かつ、従来の有機系電子写真感光体よりも優れて
おり、さらに毒性がほとんどないためセレン系に替わる
電子写真感光体として利用できる。
Perylene pigment as a bisazo raw material (effects of the invention) As explained above, the electrophotographic sensitivity evaluated by half-reduction exposure is comparable to that of conventional selenium-based electrophotographic photoreceptors, and is superior to conventional organic electrophotographic photoreceptors. It is superior to the human body and has almost no toxicity, so it can be used as an electrophotographic photoreceptor in place of selenium-based materials.

Claims (1)

【特許請求の範囲】[Claims] (1)電荷発生層と電荷移動層からなる二層式電子写真
感光体において、主鎖がケイ素の連鎖よりなり、側鎖が
アルキル置換アリール基よりなる高分子化合物で電荷移
動層を構成した電子写真感光体。
(1) In a two-layer electrophotographic photoreceptor consisting of a charge generation layer and a charge transfer layer, the charge transfer layer is made of a polymer compound whose main chain is a silicon chain and whose side chain is an alkyl-substituted aryl group. Photographic photoreceptor.
JP12309588A 1988-05-20 1988-05-20 Electrophotographic photoreceptor Expired - Fee Related JP2657300B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP12309588A JP2657300B2 (en) 1988-05-20 1988-05-20 Electrophotographic photoreceptor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP12309588A JP2657300B2 (en) 1988-05-20 1988-05-20 Electrophotographic photoreceptor

Publications (2)

Publication Number Publication Date
JPH01293349A true JPH01293349A (en) 1989-11-27
JP2657300B2 JP2657300B2 (en) 1997-09-24

Family

ID=14852078

Family Applications (1)

Application Number Title Priority Date Filing Date
JP12309588A Expired - Fee Related JP2657300B2 (en) 1988-05-20 1988-05-20 Electrophotographic photoreceptor

Country Status (1)

Country Link
JP (1) JP2657300B2 (en)

Also Published As

Publication number Publication date
JP2657300B2 (en) 1997-09-24

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