JPS62269964A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPS62269964A
JPS62269964A JP11259486A JP11259486A JPS62269964A JP S62269964 A JPS62269964 A JP S62269964A JP 11259486 A JP11259486 A JP 11259486A JP 11259486 A JP11259486 A JP 11259486A JP S62269964 A JPS62269964 A JP S62269964A
Authority
JP
Japan
Prior art keywords
polysilane
electrostatic charge
transfer layer
charge transfer
layer
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
JP11259486A
Other languages
Japanese (ja)
Inventor
Tadashi Asanuma
正 浅沼
Yoshiko Tokura
十倉 由子
Ryuichi Sugimoto
隆一 杉本
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.)
Mitsui Toatsu Chemicals Inc
Original Assignee
Mitsui Toatsu Chemicals 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 Mitsui Toatsu Chemicals Inc filed Critical Mitsui Toatsu Chemicals Inc
Priority to JP11259486A priority Critical patent/JPS62269964A/en
Publication of JPS62269964A publication Critical patent/JPS62269964A/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
    • G03G5/07Polymeric photoconductive materials
    • G03G5/078Polymeric photoconductive materials comprising silicon atoms

Landscapes

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

Abstract

PURPOSE:To obtain the titled body capable of preventing changes of sensitivity and durability, etc., by using polysilane for the electrostatic charge transfer layer in the titled body composed of the two layers of the electrostatic charge generating layer and the electrostatic charge transfer layer. CONSTITUTION:The polysilane is used for the electrostatic charge transfer layer. The electrostatic charge transfer layer is formed by coating a coating solution obtd. by mixing a dispersion for forming the electrostatic charge generating layer on an aluminum plate by means of a film applicator, followed by drying the film, and subsequently by coating a solution dissolved a polysilane obtd. by effecting dehalogenation of dihalogenosilane and/or dihalogenodisilane having one of the hydrocarbon residue followed by polycondensating in toluene on the electrostatic generating layer, followed by drying it.

Description

【発明の詳細な説明】 3、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する。更に詳しくは、特定
の化合物からなる電両移動層を有する積層型電子写真を
光体に関する。
Detailed Description of the Invention 3. Detailed Description of the Invention [Field of Industrial Application] The present invention relates to an electrophotographic photoreceptor. More specifically, the present invention relates to a laminated electrophotographic light body having a charge transfer layer made of a specific compound.

(従来の技術〕 フタロシアニン系色素、ジアゾ系色素、ペリレン系色素
など種々の色素とポリビニル力ルバヅール、オキサジア
ゾール、ヒドラゾン、ピラゾリンなどを組み合わせたよ
うなlr機機台合物らなる電子写真感光体は、セレン、
硫化カドミウムなどの無機光導電性化合物からなる電子
写真感光体に比較して、無公害性、高生産性などの利点
があり、高感度でしかも耐久性に優れた組み合わせが種
々提案されている。
(Prior art) An electrophotographic photoreceptor made of an LR machine compound such as a combination of various dyes such as phthalocyanine dyes, diazo dyes, and perylene dyes with polyvinyl rubber, oxadiazole, hydrazone, pyrazoline, etc. is selenium,
Compared to electrophotographic photoreceptors made of inorganic photoconductive compounds such as cadmium sulfide, they have advantages such as non-pollution and high productivity, and various combinations of high sensitivity and excellent durability have been proposed.

〔発明が解決しようとする問題点〕[Problem that the invention seeks to solve]

上記育機化合物系の電子写真感光体は優れたものではあ
るが、電荷移動層として好適なオキサジアゾール、ヒド
ラゾン、ピラゾリンなどは単独では良好な膜とはならず
、種々のバインダーを使用する必要があり、バインダー
の特性によって感光体としての感度、耐久性等が変化す
るという問題がある。したがって、バインダーを実質的
に使用しない電荷移動層の開発が望まれている。
Although the electrophotographic photoreceptor based on the above-mentioned nurturing compound is excellent, oxadiazole, hydrazone, pyrazoline, etc., which are suitable for the charge transfer layer, do not form a good film by themselves, and various binders must be used. However, there is a problem in that the sensitivity, durability, etc. of a photoreceptor vary depending on the characteristics of the binder. Therefore, it is desired to develop a charge transport layer that does not substantially use a binder.

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

本発明者らは、上記問題点を解決する方法について鋭意
険討し、本発明を完成した。
The inventors of the present invention have conducted extensive research into ways to solve the above-mentioned problems, and have completed the present invention.

すなわち、本発明は、少なくともtr:1発生層と電荷
移動層の2F!から形成される電子写真感光体において
、咳電倚移動層としてポリシランを用いることを特徴と
する電子写真感光体であるゆ本発明において、重要なの
はt荷移動層としてボIJシランを用いることであり、
ここに用いるポリシランとしては少なくともケイ素1原
子当たり一つの炭化水素残基を有するポリシランが好ま
しい。
That is, the present invention provides at least 2F! of the tr:1 generation layer and the charge transfer layer. In the present invention, it is important to use polysilane as the charge transfer layer. ,
The polysilane used here is preferably a polysilane having at least one hydrocarbon residue per silicon atom.

このポリシランは、好ましくは少なくとも一つの炭化水
素残基を有するジハロゲノシランおよび/またはジハロ
ゲノジシランを脱ハロゲン重縮合して得られる。ここで
用いるジハロゲノシランおよびジハロゲノジシランとし
ては、ジメチルジクロルシラン、メチルフェニルジクロ
ルシラン、ジフェニルジクロルシラン、ジエチルジクロ
ルシラン、エチルフェニルジクロルシラン、ジプロピル
ジクロルシラン、プロピルフェニルジクロルシランなど
のジクロロシラン、テトラメチルジクロルシフラン、ト
リメチルフェニルジクロルジシラン、ジメチルジフェニ
ルジクロルジシラン、ジメチルジエチルジクロルジシラ
ン、トリメチルエチルジクロルジシランなどのジクロロ
ジシラン或いは上記塩化物の他にこれらの弗化物が具体
例として挙ゲられる。
This polysilane is preferably obtained by dehalogenation polycondensation of dihalogenosilane and/or dihalogenodisilane having at least one hydrocarbon residue. The dihalogenosilane and dihalogenodisilane used here include dimethyldichlorosilane, methylphenyldichlorosilane, diphenyldichlorosilane, diethyldichlorosilane, ethylphenyldichlorosilane, dipropyldichlorosilane, and propylphenyldichlorosilane. Dichlorosilane such as silane, dichlorodisilane such as tetramethyldichlorosifuran, trimethylphenyldichlorodisilane, dimethyldiphenyldichlorodisilane, dimethyldiethyldichlorodisilane, trimethylethyldichlorodisilane, or their fluorides in addition to the above chlorides is cited as a specific example.

ジハロゲノシランおよび/またはジハロゲノジシランか
ら脱ハロゲン重縮合でポリシランを製造する方法として
は特に制限はないが、上記ジハロゲノシランおよび/ま
たはジハロゲノジシランとアルカリ金属とを加熱接触処
理する方法が好ましく例示できる〔例えば、R,C,W
est、ComprehensiveOrganic 
Cbnistry、Vol、2.Chaptor9.4
.P365〜387(1982>、edlted by
 にJNk:n5on at al、、Pergamo
nPress、New、York) +1本発明におい
ては、ポリシランが電荷移動層として用いられるが、上
記ポリシランのほかに2,4゜7−ドリニトロー9−フ
リオレノン、m−ジシアノベンゼン、テトラシアノエチ
レン、フタル酸ジエステル、トリフェニルアミンなどを
併用することもできる。また、上記ポリシランを溶液な
どにして塗布乾燥して1荷移動層とした後見に紫外線等
を照射して架橋せしめておくこともできる。
There is no particular restriction on the method for producing polysilane from dihalogenosilane and/or dihalogenodisilane by dehalogenation polycondensation, but a method of heating and contacting the above dihalogenosilane and/or dihalogenodisilane with an alkali metal is preferred. For example, R, C, W
est, Comprehensive Organic
Cbnistry, Vol. 2. Chapter 9.4
.. P365-387 (1982>, edlted by
JNk:n5on at al,, Pergamo
nPress, New York) +1 In the present invention, polysilane is used as the charge transport layer, but in addition to the above polysilane, 2,4°7-dolinitro-9-furiolenone, m-dicyanobenzene, tetracyanoethylene, phthalic acid diester , triphenylamine, etc. can also be used in combination. Alternatively, the polysilane may be applied as a solution and dried to form one cargo transfer layer, which is then crosslinked by irradiation with ultraviolet rays or the like.

本発明では、上述のようにポリシランを電r@移動層と
して用いるが、電荷発生層としては、種々のものが使用
可能であり、特に制限はなく、種々の色素が好ましく使
用できる。
In the present invention, polysilane is used as the charge r@ transfer layer as described above, but various materials can be used as the charge generation layer, and there is no particular restriction, and various dyes can be preferably used.

ここに使用可能な色素としては、例えば、スーダンレッ
ド、グイアンプル−、ジェナスグリーンBなどのアゾ系
色素、アルゴール イエロー、ピレンキノン、インダン
スレンブリリアント、バイオレットRRPなどのキノン
系色素、キノシアニン系色素、インジゴ、チオインジゴ
などのインジゴ系色素、インドファストオレンジなどの
ビスベンゾイミダゾール系色素、洞フタロシアニンなど
のフタロシアニン系色素、キナクリドンなどのキナクリ
ドン系色素などが挙げられ、これらは、必要に応じ、ポ
リエステチル、ポリビニルブチラール、ポリカーボネー
トなどの有機バインダーと共に、を荷発生層に形成され
る。
Examples of pigments that can be used here include azo pigments such as Sudan Red, Guianpuru, and Jenas Green B, quinone pigments such as Algol Yellow, pyrenequinone, indanthrene brilliant, and violet RRP, quinocyanine pigments, indigo, Examples include indigo dyes such as thioindigo, bisbenzimidazole dyes such as Indofast Orange, phthalocyanine dyes such as sinus phthalocyanine, and quinacridone dyes such as quinacridone. It is formed into a load-generating layer along with an organic binder such as polycarbonate.

本発明においては、また、電荷発生層とその下に設けら
れた導電支持層の間に導電支持層から電荷発生層への自
由電荷の注入を阻止し、かつ、電荷発生層と導電支持層
の接着性を向上させるために、酸化アルミニウム、酸化
インジウム、酸化錫、ポリプロピレン樹脂、アクリル樹
脂、メタクリル樹脂、ポリ塩化ビニル樹脂、エポキソ樹
脂、ポリエステル樹脂、アルキッド樹脂、ポリウレタン
樹脂、ポリイミド樹脂などからなる層を設けることもで
きる。
In the present invention, it is also possible to prevent the injection of free charges from the conductive support layer to the charge generation layer between the charge generation layer and the conductive support layer provided thereunder, and to prevent the injection of free charges from the conductive support layer to the charge generation layer. To improve adhesion, a layer consisting of aluminum oxide, indium oxide, tin oxide, polypropylene resin, acrylic resin, methacrylic resin, polyvinyl chloride resin, epoxo resin, polyester resin, alkyd resin, polyurethane resin, polyimide resin, etc. It is also possible to provide one.

〔実施例〕〔Example〕

以下、実施例により本発明を説明する。 The present invention will be explained below with reference to Examples.

実施例1 β型銅フタロシアニン(東洋インキ製造■製、Lion
ol Blue NCB Tonor) 1重量部にト
ルエン99重量部を加え、24時間超音波分散を行った
。次ぎに飽和ポリエステル樹脂(東洋紡績■製、バイロ
ン200)の10%テトラヒドロフラン溶液50重量部
と上記分散l夜を混合した塗布液を厚さ100μのアル
ミ板上にフィルムアプリケーターを用いて塗布乾燥して
、厚さ0.5μの電荷発生層を形成した。
Example 1 β-type copper phthalocyanine (manufactured by Toyo Ink Mfg., Lion
ol Blue NCB Tonor) 99 parts by weight of toluene was added to 1 part by weight, and ultrasonic dispersion was performed for 24 hours. Next, a coating solution prepared by mixing 50 parts by weight of a 10% tetrahydrofuran solution of a saturated polyester resin (manufactured by Toyobo ■, Byron 200) and the above dispersion was applied onto a 100μ thick aluminum plate using a film applicator and dried. , a charge generation layer having a thickness of 0.5 μm was formed.

この電荷発生層の上に、ジメチルジクロロシランとメチ
ルフェニルジクロロシランを1=1の割合でトルエン中
金属ナトリウムで重縮合して得られた平均分子量20万
のポリシラン1重量部をトルエン10重量部に溶かした
液を塗布乾燥して、厚さ7μの電荷移動層を形成した。
On this charge generation layer, 1 part by weight of polysilane having an average molecular weight of 200,000 obtained by polycondensing dimethyldichlorosilane and methylphenyldichlorosilane in a ratio of 1=1 with sodium metal in toluene was added to 10 parts by weight of toluene. The dissolved solution was applied and dried to form a charge transfer layer with a thickness of 7 μm.

このようにして作成した積層型電子写真窓光体の特性を
、エレクトロスタチフクベーバーアナライダーEPA〜
8100 (川口電気■製)を用いて測定した。まず、
−6kVのコロナ放電を2秒間行い、初期表面電位を測
定した後、暗所に2秒間放置し、次いでカラーガラスフ
ィルターIR−80(保谷硝子■製)を通し、照度20
 luxの光をあてて半減期露光量を測定した。結果を
表−1に示す。
The characteristics of the laminated electrophotographic window light material created in this way were evaluated using the Electrostatifuku Weber Analyzer EPA ~
8100 (manufactured by Kawaguchi Denki ■). first,
After performing corona discharge at -6 kV for 2 seconds and measuring the initial surface potential, it was left in a dark place for 2 seconds, and then passed through a color glass filter IR-80 (manufactured by Hoya Glass) and
The half-life exposure amount was measured by applying lux light. The results are shown in Table-1.

実施例2〜5 ポリシランに対し表−1に示す増悪剤を表−1に示す量
添加した以外は、実施例1と同様にして積層型電子写真
窓光体を製造し、得られた怒光体の特性を実施例1と同
様に測定した。結果を表−1に示す。
Examples 2 to 5 A laminated electrophotographic window illuminator was produced in the same manner as in Example 1, except that the exacerbating agent shown in Table 1 was added to the polysilane in the amount shown in Table 1, and the obtained bright light Body characteristics were measured in the same manner as in Example 1. The results are shown in Table-1.

実施例6 β型銅フタロシアニンに代えて、下記構造式で示される
アゾ系色素(特開昭53−133299号公報の実施例
に従って合成した。)を用いた以外は、実施例1と同様
にして電荷発生層を形成した。
Example 6 In the same manner as in Example 1, except that an azo dye represented by the following structural formula (synthesized according to the example of JP-A-53-133299) was used instead of β-type copper phthalocyanine. A charge generation layer was formed.

次ぎに、実施例1で用いたと同じポリシラン5重量部と
トリフェニルアミン1重量部をクロロホルム50重量部
に溶解した液を上記電荷発生層の上に塗布乾燥して、電
荷移動層を形成した。
Next, a solution prepared by dissolving 5 parts by weight of the same polysilane used in Example 1 and 1 part by weight of triphenylamine in 50 parts by weight of chloroform was applied onto the charge generation layer and dried to form a charge transfer layer.

得られた積層型電子写真窓光体の初期表面電位および半
減期露光量は、それぞれ−447v、761uχ・se
cであった。
The initial surface potential and half-life exposure of the obtained laminated electrophotographic window illuminator were -447v and 761uχ·se, respectively.
It was c.

〔発明の効果〕〔Effect of the invention〕

本発明の電子写真複写機は電子写真複写機に利用できる
のみならず、レーザー・プリンター、CRTプリンター
、電子写真式製版システムなどの電子写真応用分野に広
く用いることができ、工業的に価値がある。
The electrophotographic copying machine of the present invention can be used not only as an electrophotographic copying machine but also in a wide range of electrophotographic application fields such as laser printers, CRT printers, and electrophotographic plate making systems, and has industrial value. .

Claims (1)

【特許請求の範囲】 1、少なくとも電荷発生層と電荷移動層の2層から形成
される電子写真感光体において、該電荷移動層としてポ
リシランを用いることを特徴とする電子写真感光体。 2、ポリシランが少なくとも一つの炭化水素基を有する
ジハロゲノシランおよび/またはジハロゲノジシランを
脱ハロゲン重縮合して得たものである特許請求の範囲第
1項記載の電子写真感光体。
Claims: 1. An electrophotographic photoreceptor formed of at least two layers, a charge generation layer and a charge transfer layer, characterized in that polysilane is used as the charge transfer layer. 2. The electrophotographic photoreceptor according to claim 1, wherein the polysilane is obtained by dehalogenation polycondensation of a dihalogenosilane and/or a dihalogenodisilane having at least one hydrocarbon group.
JP11259486A 1986-05-19 1986-05-19 Electrophotographic sensitive body Pending JPS62269964A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP11259486A JPS62269964A (en) 1986-05-19 1986-05-19 Electrophotographic sensitive body

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP11259486A JPS62269964A (en) 1986-05-19 1986-05-19 Electrophotographic sensitive body

Publications (1)

Publication Number Publication Date
JPS62269964A true JPS62269964A (en) 1987-11-24

Family

ID=14590645

Family Applications (1)

Application Number Title Priority Date Filing Date
JP11259486A Pending JPS62269964A (en) 1986-05-19 1986-05-19 Electrophotographic sensitive body

Country Status (1)

Country Link
JP (1) JPS62269964A (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6488461A (en) * 1987-09-29 1989-04-03 Nippon Shizai Kk Photosensitive body
JPH01231059A (en) * 1988-03-11 1989-09-14 Nippon Telegr & Teleph Corp <Ntt> Electrophotographic sensitive body
JPH02140753A (en) * 1988-11-21 1990-05-30 Toyo Ink Mfg Co Ltd Electrophotographic sensitive body
EP0403662A1 (en) * 1988-12-29 1990-12-27 Canon Kabushiki Kaisha Polysilane compound and electrophotographic photoreceptor produced therefrom
WO1991005018A1 (en) * 1989-09-27 1991-04-18 Canon Kabushiki Kaisha Novel polysilane composition
DE4039519A1 (en) * 1989-12-11 1991-06-13 Canon Kk Barrier layer organic photo-element - has poly:silane organic semiconductor layer used e.g. metal- or semiconductor-insulator-semiconductor Schottky transition
JPH03144576A (en) * 1989-10-31 1991-06-19 Mita Ind Co Ltd Photosensitive body
JPH03263050A (en) * 1990-03-13 1991-11-22 Canon Inc Electrophotographic sensitive body
JPH04310962A (en) * 1991-01-14 1992-11-02 Xerox Corp Organic composition and photoconductive picture forming member
US5220181A (en) * 1989-12-11 1993-06-15 Canon Kabushiki Kaisha Photovoltaic element of junction type with an organic semiconductor layer formed of a polysilane compound
US5278014A (en) * 1991-06-21 1994-01-11 Konica Corporation Electrophotographic photoreceptor
US5935747A (en) * 1996-06-07 1999-08-10 Canon Kabushiki Kaisha Electrophotographic photosensitive member, and process cartridge and electrophotographic apparatus having the electrophotographic photosensitive member
EP0905172A4 (en) * 1996-06-07 1999-10-20 Osaka Gas Co Ltd Polysilanes and positive hole transporting materials

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6488461A (en) * 1987-09-29 1989-04-03 Nippon Shizai Kk Photosensitive body
JPH01231059A (en) * 1988-03-11 1989-09-14 Nippon Telegr & Teleph Corp <Ntt> Electrophotographic sensitive body
JPH02140753A (en) * 1988-11-21 1990-05-30 Toyo Ink Mfg Co Ltd Electrophotographic sensitive body
US5159042A (en) * 1988-12-29 1992-10-27 Canon Kabushiki Kaisha Polysilane compounds and electrophotographic photosensitive members with the use of said compounds
EP0403662A1 (en) * 1988-12-29 1990-12-27 Canon Kabushiki Kaisha Polysilane compound and electrophotographic photoreceptor produced therefrom
EP0403662B1 (en) * 1988-12-29 1995-03-22 Canon Kabushiki Kaisha Polysilane compound and electrophotographic photoreceptor produced therefrom
WO1991005018A1 (en) * 1989-09-27 1991-04-18 Canon Kabushiki Kaisha Novel polysilane composition
US5358987A (en) * 1989-09-27 1994-10-25 Canon Kabushiki Kaisha Polysilane compositions
JPH03144576A (en) * 1989-10-31 1991-06-19 Mita Ind Co Ltd Photosensitive body
US5220181A (en) * 1989-12-11 1993-06-15 Canon Kabushiki Kaisha Photovoltaic element of junction type with an organic semiconductor layer formed of a polysilane compound
DE4039519A1 (en) * 1989-12-11 1991-06-13 Canon Kk Barrier layer organic photo-element - has poly:silane organic semiconductor layer used e.g. metal- or semiconductor-insulator-semiconductor Schottky transition
JPH03263050A (en) * 1990-03-13 1991-11-22 Canon Inc Electrophotographic sensitive body
JPH04310962A (en) * 1991-01-14 1992-11-02 Xerox Corp Organic composition and photoconductive picture forming member
US5278014A (en) * 1991-06-21 1994-01-11 Konica Corporation Electrophotographic photoreceptor
US5935747A (en) * 1996-06-07 1999-08-10 Canon Kabushiki Kaisha Electrophotographic photosensitive member, and process cartridge and electrophotographic apparatus having the electrophotographic photosensitive member
EP0905172A4 (en) * 1996-06-07 1999-10-20 Osaka Gas Co Ltd Polysilanes and positive hole transporting materials

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