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JPS6059589B2 - electrophotographic photoreceptor - Google Patents
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JPS6059589B2 - electrophotographic photoreceptor - Google Patents

electrophotographic photoreceptor

Info

Publication number
JPS6059589B2
JPS6059589B2 JP55146240A JP14624080A JPS6059589B2 JP S6059589 B2 JPS6059589 B2 JP S6059589B2 JP 55146240 A JP55146240 A JP 55146240A JP 14624080 A JP14624080 A JP 14624080A JP S6059589 B2 JPS6059589 B2 JP S6059589B2
Authority
JP
Japan
Prior art keywords
carrier
group
layer
carrier transport
general 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.)
Expired
Application number
JP55146240A
Other languages
Japanese (ja)
Other versions
JPS5770535A (en
Inventor
良明 武居
直子 明石
弘之 野守
聰 後藤
昭 木下
恒夫 和田
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 JP55146240A priority Critical patent/JPS6059589B2/en
Publication of JPS5770535A publication Critical patent/JPS5770535A/en
Publication of JPS6059589B2 publication Critical patent/JPS6059589B2/en
Expired 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 or to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664Dyes
    • G03G5/0666Dyes containing a methine or polymethine group
    • G03G5/0668Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • 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 or to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0609Acyclic or carbocyclic compounds containing oxygen
    • 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 or to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0612Acyclic or carbocyclic compounds containing nitrogen
    • 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 or to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0612Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0616Hydrazines; Hydrazones
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/04Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601Acyclic or carbocyclic compounds
    • G03G5/0618Acyclic or carbocyclic compounds containing oxygen and nitrogen

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Light Receiving Elements (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Description

【発明の詳細な説明】 本発明は導電性支持体上に、キャリア発生相とキャリア
輸送相とを組合わせてなる感光層を設けた電子写真感光
体に関するものてある。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor in which a photosensitive layer comprising a combination of a carrier generation phase and a carrier transport phase is provided on a conductive support.

一般に可視光を吸収してキャリアを発生する物質は、無
定形セレン等のごく部のものを除いては、それ自体でフ
ィルムを形成せしめることが困難であり、しかもその表
面に与えられた電荷に対する保持力に乏しい欠へを有し
ている。
In general, it is difficult for substances that absorb visible light to generate carriers to form a film on their own, with the exception of a small number of substances such as amorphous selenium. It has a lack of holding power.

これと逆に、フィルム形成能に優れ、かつ10ミクロン
程度の厚さで500V以上の電荷を長時間に亘つて保持
し得る物質は、概して可視光の吸収による十分な光導電
性を有しない欠点を有している。このような理由から、
最近、可視光を吸収して荷電キャリアを発生する物質に
よるキャリア発生相と、このキャリア発生相で発生した
荷電キャリアの正負いずれか一方又は両方の輸送を行う
キャリア輸送相とを組合わせて感光層を構成せしめるこ
とが提案された。
On the contrary, materials that have excellent film-forming ability and can retain a charge of 500 V or more for a long time with a thickness of about 10 microns generally have the disadvantage of not having sufficient photoconductivity due to absorption of visible light. have. For this reason,
Recently, photosensitive layers have been developed by combining a carrier generation phase made of a substance that absorbs visible light and generates charge carriers, and a carrier transport phase that transports either positive or negative charge carriers or both of the charge carriers generated in this carrier generation phase. It was proposed to configure the

このように、荷電キャリアの発生と輸送とをを別個の相
に分坦さることによつて、材料の選択範囲が広くなり、
電子写真プロセJスズにおいて要求される諸特性、例え
ば電荷保持力、表面強度、可視光に対する感度及び反復
使用時における安定性等を向上又は改善せしめることが
できるようになつた。従来このような感光体としては、
次のようなも・のが知られている。
In this way, by separating the generation and transport of charge carriers into separate phases, the range of material selection is widened.
It has become possible to enhance or improve various properties required for electrophotographic process J tin, such as charge retention, surface strength, sensitivity to visible light, and stability during repeated use. Conventionally, such photoreceptors include:
The following are known:

(1)キャリア発生相の層(以下単に1キャリア発生層
ョという。
(1) Carrier generation phase layer (hereinafter simply referred to as 1 carrier generation layer).

)を無定形セレンにより構成し、キャリア輸送相の層(
以下単に1キャリア輸送層ョという。)をポリーN−ビ
ニルカルバゾール(以下 RpvKJと言う。
) is composed of amorphous selenium, and the carrier transport phase layer (
Hereinafter, it will simply be referred to as the 1 carrier transport layer. ) is poly N-vinylcarbazole (hereinafter referred to as RpvKJ).

)により構成して積層せしめた感光層を有するもの(2
)キャリア発生層を無定形セレンにより構成し、キャリ
ア輸送層を2,4,7−トリニロー9−フルオレノン(
以下RTNFJと言う。
) having a photosensitive layer formed and laminated (2)
) The carrier generation layer is composed of amorphous selenium, and the carrier transport layer is composed of 2,4,7-trinylo-9-fluorenone (
Hereafter referred to as RTNFJ.

)により構成して積層せさめた感光層を有するもの(3
)キャリア発生層をペリレン誘導体により構成し、キャ
リア輸送層をオキサジアゾール誘導体により構成して積
層せしめた感光層を有するもの(米国特許第38718
8汚明細書参照)(4)キャリア発生層をクロルダイア
ンブルー又はメチルスカリリウムにより構成し、キャリ
ア輸送層をピラゾリン誘導体により構成して積層せしめ
た感光層を有するもの(特開昭51−90827号公報
参照)(5)PVKを含有するキャリア輸送相中にキャ
リア発生相を構成するフタロシアニンを分散せしめた感
光層を有するもの(6)゛へNFを含有するキャリア輸
送相中にキャリア発生相を構成するフタロシアニンを分
散せしめた感光層を有するもの以上のように多くの二相
構成を有する感光層を具えた電子写真感光体が知られて
いるが、製造が容易であり、十分な電子写真感光体を有
し、しかも環境の変化に対して安定性を有する優れた電
子写真感光体は現在迄知らていない。
) having a laminated photosensitive layer (3)
) A photosensitive layer in which the carrier generation layer is composed of a perylene derivative and the carrier transport layer is composed of an oxadiazole derivative (US Pat. No. 38718)
(4) A photosensitive layer in which the carrier generation layer is composed of chlordian blue or methylscarillium and the carrier transport layer is composed of a pyrazoline derivative (Japanese Patent Laid-Open No. 51-90827) (Refer to the publication) (5) A photosensitive layer having a photosensitive layer in which phthalocyanine constituting a carrier generation phase is dispersed in a carrier transport phase containing PVK (6) A structure in which a carrier generation phase is constituted in a carrier transport phase containing NF Electrophotographic photoreceptors having a photosensitive layer having a two-phase structure are known, such as those having a photosensitive layer having a phthalocyanine dispersed therein. To date, no excellent electrophotographic photoreceptor has been known that has the following characteristics and is stable against environmental changes.

例えば、PVKを用いてキャリア輸送層を構成せしめる
場合には、その塗膜が乾燥工程において著しく収縮し、
このため形成される感光層が導電性支持体から剥離する
ようになる欠点がある。又、TNF又はオキサジアゾー
ル誘導体を樹脂結合剤と共に溶剤に溶解してキャリア輸
送相又はキャリア輸送層を形成せしめる場合には、しば
しば上記化合物の結晶析出が起る欠点がある。又、クロ
ルダイアンブルー、スカリリウム等の有機顔料を用いて
キャリア発生層を構成せしめ、種々の置換基を有するピ
ラゾリン誘導体又はPVKを含有せしめてキャリア輸送
層を構成せしめた二層構造の感光体における。
For example, when PVK is used to construct a carrier transport layer, the coating film shrinks significantly during the drying process.
For this reason, there is a drawback that the formed photosensitive layer peels off from the conductive support. Furthermore, when TNF or an oxadiazole derivative is dissolved in a solvent together with a resin binder to form a carrier transport phase or carrier transport layer, there is a drawback that crystal precipitation of the above-mentioned compound often occurs. Further, in a photoreceptor having a two-layer structure, a carrier generation layer is formed using an organic pigment such as chlordian blue or scarillium, and a carrier transport layer is formed using a pyrazoline derivative having various substituents or PVK.

キャリア発生層からキャリア輸送層への正符号キャリア
(ホール)の注入効率に関するメルツ氏の研究によれば
、PVKをキャリア輸送層の材質として用いた場合の注
入効率が最も低く、ピラゾリソ誘導体を用いた場合には
置換基の種類によつて注入効率が大きく変り、又キャリ
ア発生層に対しキャリア輸送物質のイオン化ポテンシャ
ルが低い程注入効率が大きくなるとされている。然るに
無定形セレンより成るキャリア発生層に対してはPVK
は良好なキャリア輸送層を構成し得る。
According to Merz's research on the injection efficiency of positive-sign carriers (holes) from the carrier generation layer to the carrier transport layer, the injection efficiency was the lowest when PVK was used as the material for the carrier transport layer, and the injection efficiency was the lowest when PVK was used as the material for the carrier transport layer. In some cases, the injection efficiency varies greatly depending on the type of substituent, and it is said that the lower the ionization potential of the carrier transport substance relative to the carrier generation layer, the higher the injection efficiency. However, for the carrier generation layer made of amorphous selenium, PVK
can constitute a good carrier transport layer.

このようにある特定のキャリア発生物質に対して有効な
キャリア輸送物質が、他のキャリア発生物質に対して常
に有効な訳ではなく、、又特定のキャリア輸送物質に対
して有効なキャリア発生物質が、他のキャリア輸送物質
に対して常に有効であるとも言うことはできない。両物
質の組合せが不適当な場合には電子写真感度が低くなる
ばかりでなく、特に低電解時の放電効率が悪いため、所
謂残留電位が大きくなり、最悪の場合には反復して使用
する度に電位が蓄積し、実用上電子写真の用途に供し得
なくなる。このようにキャリア発生相の構成物質とキャ
リア輸送相の構成物質との好適な組合せについては法則
的な選択手段はなく、多くの物質群の中から有利な組合
せを実践的に決定する必要がある。
In this way, a carrier transporting substance that is effective against a specific carrier-generating substance is not always effective against other carrier-generating substances, and a carrier-generating substance that is effective against a specific carrier-generating substance is not always effective against other carrier-generating substances. However, it cannot be said that it is always effective for other carrier transport substances. If the combination of these two substances is inappropriate, not only will the electrophotographic sensitivity become low, but also the discharge efficiency will be poor especially at low electrolytes, so the so-called residual potential will increase, and in the worst case, repeated use will cause damage. Potential accumulates in the area, making it practically unusable for electrophotographic purposes. In this way, there is no legal way to select a suitable combination of the constituent substances of the carrier generation phase and the constituent substances of the carrier transport phase, and it is necessary to practically determine an advantageous combination from among many substance groups. .

本発明は以上の如き従来の電子写真感光体の欠点を有さ
ず、可視光に対する感度が非常に高く、従つて鮮明な画
像を常に形成することのできる電子写真感光体を提供す
ることを目的とする。又本発明の他の目的は、高い感度
を有し、しかも機械的強度が大きいと共に残留電位が極
めて低く、従つて反復使用に十分に供することのできる
電子写真感光体を提供するにある。以下図面によつて本
発明にいて説明する。
An object of the present invention is to provide an electrophotographic photoreceptor that does not have the drawbacks of conventional electrophotographic photoreceptors as described above, has very high sensitivity to visible light, and can therefore always form clear images. shall be. Another object of the present invention is to provide an electrophotographic photoreceptor that has high sensitivity, high mechanical strength, and extremely low residual potential, and can therefore be used repeatedly. The present invention will be explained below with reference to the drawings.

本発明においては、第1図に示すように、導電性支持体
1上に後述するキャリア発生物質を主成分として含有し
て成るキャリア発生層2を形成せしめ、このキャリア発
生層2上に後述するキャリア輸送物質を主成分として含
有して成るキャリア輸送層3を積層して形成せしめ、前
記キャリア発生層2とキャリア輸送層3とにより感光層
4を構成せしめる。
In the present invention, as shown in FIG. 1, a carrier generation layer 2 containing a carrier generation substance described later as a main component is formed on a conductive support 1, and a carrier generation layer 2 containing a carrier generation substance described below as a main component is formed on this carrier generation layer 2. A carrier transport layer 3 containing a carrier transport substance as a main component is laminated to form a photosensitive layer 4. The carrier generation layer 2 and the carrier transport layer 3 constitute a photosensitive layer 4.

ここで前記導電性支持体1の材質としては、例えばアル
ミニウム、ニッケル、銅、亜鉛、パラジウム、銀、イン
ジウム、錫、白金、金、ステンレス鋼、真鍮等の金属の
シートを用いることができるが、これらに限定されるも
のではなく、例えば第2図に示すように絶縁性基体1A
上に、導電層1Bを設けて導電性支持体1を構成せしめ
ることもできる。
Here, as the material of the conductive support 1, for example, a sheet of metal such as aluminum, nickel, copper, zinc, palladium, silver, indium, tin, platinum, gold, stainless steel, brass, etc. can be used. For example, as shown in FIG. 2, the insulating substrate 1A
The conductive support 1 can also be configured by providing a conductive layer 1B thereon.

この場合において、基体1Aとしては紙、プラスチック
シート等の可撓性を有し、しかも曲げ、引張り等の応力
に対しても十分な強度を有するものが適当である。又導
電層1Bは、金属シートをラミネートし或いは金属を真
空蒸着せしめることにより、又はその他の方法によつて
設けることができる。前記キャリア発生層2は、後述す
るキャリア発生物質単独により、又はこれに適当なバイ
ンダー”樹脂を加えたものにより、或いは更に特定乃至
非特定の極性のキャリアに対する移動度の大きいい物質
即ちキャリア輸送物質を添加したものにより形成するこ
とができる。
In this case, the substrate 1A is suitably flexible, such as paper or a plastic sheet, and has sufficient strength against stress such as bending and tension. The conductive layer 1B can also be provided by laminating metal sheets, vacuum depositing metal, or by other methods. The carrier generation layer 2 may be made of a carrier generation substance alone, which will be described later, or a suitable binder resin added thereto, or a substance with high mobility for carriers of specific or non-specific polarity, that is, a carrier transport substance. It can be formed by adding .

具体的な形成法としては、前記支持体上にキャリア発生
物質を真空蒸着せしめる方法、キャリア発生物質を適当
な溶剤に溶解若しくは分散せしめたものを塗布して乾燥
せしめる方法を挙げることができる。
Specific forming methods include a method in which a carrier-generating substance is vacuum-deposited on the support, and a method in which a carrier-generating substance dissolved or dispersed in a suitable solvent is coated and dried.

この後者の方法においては、バインダー樹脂若jしくは
キャリア輸送物質を添加してもよく、その場合における
、キャリア発生物質:バインダー樹脂:キヤリア輸送物
質の割合は、重量比で1:0〜100:0〜50代特に
1:0〜10:0〜50であることが好ましい。
In this latter method, a binder resin or a carrier transport substance may be added, and in this case, the ratio of carrier generating substance: binder resin: carrier transport substance is 1:0 to 100: by weight. The ratio is preferably 0 to 50, particularly 1:0 to 10:0 to 50.

ここに用いられるバインダー樹脂としては、例えばポリ
エチレワン、ポリプロピレン、アクリル樹脂、メタクリ
ル樹脂、塩化ビニル樹脂、酢酸ビニル樹脂、エポキシ樹
脂、ポリウレタン樹脂、フェノール樹脂、ポリエステル
樹脂、アルキッド樹脂、ポリカーボネート樹脂、シリコ
ン樹脂、メラミン樹脂等の付加重合型樹脂、重付加型樹
脂、重縮合型樹脂並びにこれらの樹脂の繰返し単位のう
ちの2つ以上を含む共重合体樹脂、例えば塩化ビニルー
酢酸ビニル共重合体樹脂、塩化ビニルー酢酸ビニルー無
水マレイン酸共重合体樹脂等を挙げることができる。
Examples of the binder resin used here include polyethylene one, polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, epoxy resin, polyurethane resin, phenol resin, polyester resin, alkyd resin, polycarbonate resin, silicone resin, Addition polymer resins such as melamine resins, polyaddition resins, polycondensation resins, and copolymer resins containing two or more repeating units of these resins, such as vinyl chloride-vinyl acetate copolymer resins, vinyl chloride-vinyl acetate copolymer resins, Examples include vinyl acetate-maleic anhydride copolymer resin.

かしバインダー樹脂はこれらに限定されるものではなく
、斯かる用途に一般に用いられるすべての樹脂を使用す
ることができる。前記キャリア発生層に加えることので
きる特定乃至非特定の極性のキャリアに対する移動度の
大きいキャリア輸送物質としては、本発明においてキャ
リア輸送層3等の構成に用いる、後述する特定のキャリ
ア輸送物質をその一部又は全部として用いることもでき
る゛が、電子写真感光体としての性能を考慮して他のキ
ャリア輸送物質を用いてもよい。更にこのキャリア発生
層には、残留電位低下剤、疲労低減剤その他を必要に応
じて含有せしめることができる。
The binder resin is not limited to these, and all resins commonly used for such purposes can be used. As the carrier transporting substance having high mobility for carriers of specific or non-specific polarity that can be added to the carrier generation layer, specific carrier transporting substances described below, which are used in the structure of the carrier transporting layer 3 etc. in the present invention, may be used. Although it may be used in part or in whole, other carrier transport materials may be used in consideration of the performance as an electrophotographic photoreceptor. Furthermore, this carrier generation layer may contain a residual potential lowering agent, a fatigue reducing agent, and the like, if necessary.

以上のようにして形成される前記キャリア発生層2の厚
さは、好ましくは0.005〜20ミクロン、特に好ま
しくは0.1〜5ミクロンである。又前記キャリア輸送
層3は、後述するヒドラゾン誘導体をキャリア輸送物質
として用い、必要に一応じて適当なバインダー樹脂、或
いは他の添加剤と共に適当な溶剤に溶解若しくは分散せ
しめて得られる塗布液を塗布し乾燥する方法、その他の
方法によつて形成することができる。ここに用いられる
バインダー樹脂としては、例.えばポリエチレン、ポリ
プロピレン、アクリル樹脂、メタクリル樹脂、塩化ビニ
ル樹脂、酢酸ビニル樹脂、エポキシ樹脂、ポリウレタン
樹脂、フェノール樹脂、ポリエステル樹脂、アルキッド
樹脂、ポリカーボネート樹脂、シリコン樹脂、メラーミ
ン樹脂等の付加重合型樹脂、重付加型樹脂、重縮合型樹
脂並びにこれらの樹脂の繰返し単位のうちの2つ以上を
含む共重合体樹脂、例えば塩化ビニルー酢酸ビニル共重
合体樹脂、塩化ビニルー酢酸ビニルー無水マレイン酸共
重合体樹脂等を挙げることができる。
The thickness of the carrier generation layer 2 formed as described above is preferably 0.005 to 20 microns, particularly preferably 0.1 to 5 microns. The carrier transport layer 3 is formed by applying a coating solution obtained by dissolving or dispersing a hydrazone derivative described below as a carrier transport substance in an appropriate solvent together with an appropriate binder resin or other additives as necessary. It can be formed by a drying method or other methods. Examples of the binder resin used here include: For example, addition polymer resins such as polyethylene, polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, epoxy resin, polyurethane resin, phenol resin, polyester resin, alkyd resin, polycarbonate resin, silicone resin, melamine resin, polymer Addition type resins, polycondensation type resins, and copolymer resins containing two or more of the repeating units of these resins, such as vinyl chloride-vinyl acetate copolymer resins, vinyl chloride-vinyl acetate-maleic anhydride copolymer resins, etc. can be mentioned.

しかしバインダー樹脂はこれらに限定されるものではな
く、斯かる用途に一般に用いられるすべての樹脂を使用
することができる。こののバインダー樹脂とキャリア輸
送物質との配合割合は、バインダー樹脂10鍾量部当り
キャリア輸送物質を10〜50濾量部とするのが好まし
く、バインダー樹脂としてポリカーボネートを用いる場
合はその10鍾量部当り20〜10轍量部のキャリア輸
送物質を用いると、優れた電子写真特性が得られるので
好ましい。
However, the binder resin is not limited to these, and all resins commonly used for such purposes can be used. The blending ratio of the binder resin and the carrier transport substance is preferably 10 to 50 parts by weight of the carrier transport substance per 10 parts by weight of the binder resin, and when polycarbonate is used as the binder resin, 10 parts by weight of the carrier transport substance. It is preferable to use 20 to 10 parts per rut of carrier transport material since excellent electrophotographic properties can be obtained.

このキャリア輸送層3の厚さは2〜100ミクロン、好
ましくは5〜30ミクロンである。而して本発明におい
て、前記キャリア発生層2にその主成分として含有せし
めるキャリア発生物質は、次の一般式〔A〕,〔B〕及
び〔C〕に示される化合物から選んだものである。
The thickness of this carrier transport layer 3 is between 2 and 100 microns, preferably between 5 and 30 microns. In the present invention, the carrier generating substance contained in the carrier generating layer 2 as its main component is selected from compounds represented by the following general formulas [A], [B] and [C].

一般式〔A〕 一般式〔B〕 一般式〔C〕 上式中、Xはノ田ゲン原子、ニトロ基、シアノ基、アシ
ル基又はカルボキシル基を表わし、nは0〜4の整数を
、mはO〜6の整数を表わす。
General formula [A] General formula [B] General formula [C] In the above formula, represents an integer from 0 to 6.

一般式〔A〕で示されるアントアントロン系顔料の具体
的化合物例を挙げると次の通りである。一般式〔B〕で
示されるジベンズピレンキノン系顔料の具体的化合物例
を挙げると次の通りであ一般式〔C〕で示されるピラン
トロン系顔料の具体的化合物例を挙げると次の通りであ
る。又本発明において、前記キャリア輸送層3にその主
成分として含有せしめるキャリア輸送物質は、次の一般
式〔P〕で示されるヒドラゾン誘導体から選んだもので
ある。(式中、R1はアルキル基、フェニル基又はベン
ジル基を、R2はアルキル基、フェニル基又はベンジル
基を、R,は水素原子又はアルキル基を、 R4は水素原子又アルキル基を、 R5は水素原子又はアルコキシ基を、 lは水素原子、アルキル基又はアルコキシ基を、R7は
水素原子又はアルキル基を、 R8は水素原子、アルキル基、アルコキシ基、ジアルキ
ルアミノ基又は複素環基を、表わし、 nはR3が水素原子である場合には1を、R3がアルキ
ル基である場合には1又はOを、表わす。
Specific examples of compounds of the anthoanthrone pigment represented by the general formula [A] are as follows. Specific compound examples of the dibenzpyrenequinone pigment represented by the general formula [B] are as follows; Specific compound examples of the pyranthrone pigment represented by the general formula [C] are as follows. be. In the present invention, the carrier transport material contained in the carrier transport layer 3 as a main component is selected from hydrazone derivatives represented by the following general formula [P]. (In the formula, R1 is an alkyl group, phenyl group or benzyl group, R2 is an alkyl group, phenyl group or benzyl group, R is a hydrogen atom or an alkyl group, R4 is a hydrogen atom or an alkyl group, R5 is hydrogen an atom or an alkoxy group, l represents a hydrogen atom, an alkyl group, or an alkoxy group, R7 represents a hydrogen atom or an alkyl group, R8 represents a hydrogen atom, an alkyl group, an alkoxy group, a dialkylamino group, or a heterocyclic group, n represents 1 when R3 is a hydrogen atom, and represents 1 or O when R3 is an alkyl group.

)この一般式〔P〕で示されるヒドラゾン誘導体の代表
的具体例を挙げると次の通りである。
) Representative specific examples of the hydrazone derivative represented by the general formula [P] are as follows.

上述のヒドラゾン誘導体は1種のみでなく、2種以上の
ものの混合体、更にはその1種又は2種以上のものと他
のキャリア輸送物質の1種又は2種以上との混合体を用
いることもできる。そして最後の場合においては、前記
ヒドラゾン誘導体と当該他のキャリア輸送物質とにより
電荷移動錯伸を形成せしめ得る可能性があり、そうする
ことによつて、当該キャリア輸送層における特定符号の
キャリアの移動度を任意に制御することが可能となり、
また内部トラップを有効に消失せしめることも可能とな
る。更にこのキャリア輸送層には、適当な可塑剤、残留
電位低下剤、疲労低減剤、その他を必要に応じて含有せ
しめることができる。本発明電子写真感光体は以上のよ
うな構成であるから、、後述する実施例及び比較例から
も明らかなように、従来の二層感光層を有するものに辻
して極めて感度が高く、しかもその最大分光感度を可視
光領域の中央部分に有するため感色性が佛れ、このの結
果解像力及び階調再現性の極めて捜・好な複写画像を形
成せしめることができる。又本発明電子写真感光体は、
電荷の保持力及び表面強度が大きく、しかも残留電位が
極めて倶く、従つて反復使用においても安定に性能が発
揮され又電荷の蓄積も生じない。尚キャリア発生層2お
よびキャリア輸送層3の形成において膜体の収縮或いは
含有物質の結晶析出が起こらず、従つて剥離、白濁の問
題は生じない。
The above-mentioned hydrazone derivatives may be used not only one type, but also a mixture of two or more types, and further a mixture of one or more of the hydrazone derivatives and one or more other carrier transport substances. You can also do it. In the last case, there is a possibility that the hydrazone derivative and the other carrier transport substance can form a charge transfer complex, thereby causing a specific sign of carrier movement in the carrier transport layer. It becomes possible to control the degree arbitrarily,
It also becomes possible to effectively eliminate internal traps. Furthermore, this carrier transport layer may contain a suitable plasticizer, residual potential lowering agent, fatigue reducing agent, and others as required. Since the electrophotographic photoreceptor of the present invention has the above-mentioned structure, as is clear from the Examples and Comparative Examples described later, it has extremely high sensitivity compared to conventional photoreceptors having two photosensitive layers. Since its maximum spectral sensitivity is in the central part of the visible light region, the color sensitivity is poor, and as a result, it is possible to form a copied image with extremely good resolution and gradation reproducibility. Further, the electrophotographic photoreceptor of the present invention includes:
It has high charge retention and surface strength, and has an extremely low residual potential, so it exhibits stable performance even after repeated use and does not accumulate charge. Note that during the formation of the carrier generation layer 2 and the carrier transport layer 3, shrinkage of the film body or crystallization of the contained substance does not occur, and therefore problems of peeling and clouding do not occur.

本発明においては、第3図に示すように、導笥)性支持
体1上に中間層5を設け、これを介してキャリア発生層
2を形成し、その上にキャリア輸送層3を形成してもよ
い。
In the present invention, as shown in FIG. 3, an intermediate layer 5 is provided on a conductive support 1, a carrier generation layer 2 is formed thereon, and a carrier transport layer 3 is formed thereon. It's okay.

この中間層5は、感光層4の帯電時において導電性支持
体1から感光層4へのフリーキャリアの注入を阻止する
と共に、感光層4を導電性支持体1に対して一体的に接
着保持せしめる接着層としての作用を果す。この中間層
5の材質としては、酸化アルミニウム、酸化インジウム
等の金属酸化物、アクリル樹脂、メタクリル樹脂、塩化
ビニル樹脂、酢酸ビニル樹脂、エポキシ樹脂、ポリウレ
タン樹脂、フェノール樹脂、ポリエステル樹脂、アルキ
ド樹脂、ポリカーボネート樹脂、シリコン樹脂、メラミ
ン樹脂、塩化ビニルー酢酸ビニル共重合体樹脂、塩化ビ
ニルー酢酸ビニルー無水マレイン酸共重合体樹脂等の高
分子物質を用いることができる。又第4図に示すように
、導電性支持体1上に、前記中間層5を介して、又は介
さずに、キャリア輸送層3を形成してその上にキャリア
発生層2を形成して感光層4を構成せしめてもよい。
This intermediate layer 5 prevents the injection of free carriers from the conductive support 1 to the photosensitive layer 4 when the photosensitive layer 4 is charged, and also holds the photosensitive layer 4 integrally bonded to the conductive support 1. Acts as an adhesive layer that binds. Materials for this intermediate layer 5 include metal oxides such as aluminum oxide and indium oxide, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, epoxy resin, polyurethane resin, phenol resin, polyester resin, alkyd resin, and polycarbonate. Polymer materials such as resins, silicone resins, melamine resins, vinyl chloride-vinyl acetate copolymer resins, vinyl chloride-vinyl acetate-maleic anhydride copolymer resins can be used. Further, as shown in FIG. 4, a carrier transport layer 3 is formed on the conductive support 1 with or without the intermediate layer 5, and a carrier generation layer 2 is formed thereon. Layer 4 may also be configured.

更に第5図に示すように、既述のヒドラゾン誘導体を含
有するキャリア輸送相31中に、既述のキャリア発生物
質21を分散せしめてキャリア発生相を形成せしめるこ
とにより、感光層4を構成せしめることもできる。
Further, as shown in FIG. 5, the photosensitive layer 4 is formed by dispersing the above-mentioned carrier-generating substance 21 in the carrier-transporting phase 31 containing the above-mentioned hydrazone derivative to form a carrier-generating phase. You can also do that.

この場合においては、キャリア輸送相31を形成する材
質10踵量部に対し、キャリア発生物質を0.1〜10
0重量部、好ましくは1〜50重量部の割合で分散せし
めればよい。キャリア発生物質の割合が過小であると感
光体としての感度が小さくなり、又当該割合が過大であ
ると一般に感光層4の強度が小さくなる。以上のように
本発明においては種々の機械的構成を採用し得るが、斯
かる機械的鹸構成と共に、電子写真プロセスにおいて感
光層4を何れのの極性に帯電せしめるか等については当
業者において.好ましいものを選定することができよう
In this case, 0.1 to 10 parts of the carrier generating substance is added to 10 parts of the material forming the carrier transport phase 31.
It may be dispersed in a proportion of 0 parts by weight, preferably 1 to 50 parts by weight. If the proportion of the carrier-generating substance is too small, the sensitivity of the photoreceptor will be reduced, and if the proportion is too large, the strength of the photosensitive layer 4 will generally be reduced. As described above, various mechanical configurations can be employed in the present invention, but those skilled in the art will not be able to determine which polarity to charge the photosensitive layer 4 in the electrophotographic process in addition to such mechanical configurations. You can choose the one you like.

以下本発明の実施例について説明するが、これらによつ
て本発明が限定されるものではない。
Examples of the present invention will be described below, but the present invention is not limited thereto.

実施例1厚さ100ミクロンのポリエチレンテレフタレ
ー.トより成る基体上にアルミニウムを蒸着して成る導
電性支持体に、例示キャリア発生物質〔A3〕(アント
アントロン系顔料1モノライトレッド2YョC.I−N
O.593OO)を、2〜3×10−4T0rr′の真
空雰囲気中において蒸発源温度350℃て3分間蒸,着
せしめ、厚さ約0.5ミクロンのキャリア発生層を形成
した。
Example 1 Polyethylene terephthalate with a thickness of 100 microns. An exemplary carrier-generating substance [A3] (anthorone pigment 1 monolite red 2Y C.I-N
O. 593OO) was evaporated and deposited for 3 minutes at an evaporation source temperature of 350 DEG C. in a vacuum atmosphere of 2 to 3.times.10@-4 TOrr' to form a carrier generation layer with a thickness of about 0.5 micron.

次に例示ヒドラゾン誘導体〔P1)7.5gと、ポリカ
ーボネート樹脂1パンライトL−1250J(帝人化成
社製)10gとをテトラヒドロフラン100m1中に溶
解し、この溶液をドクターブレードを用いて前記キャリ
ア発生層上に塗布し、温度70℃で1時間乾燥せしめて
厚さ約10ミクロンのキャリア輸送層を形成し、以つて
本発明電子写真感光体を作製した。
Next, 7.5 g of the exemplified hydrazone derivative [P1] and 10 g of polycarbonate resin 1 Panlite L-1250J (manufactured by Teijin Chemicals) were dissolved in 100 ml of tetrahydrofuran, and this solution was poured onto the carrier generation layer using a doctor blade. A carrier transport layer having a thickness of about 10 microns was formed by coating the carrier and drying it at a temperature of 70° C. for 1 hour, thereby producing an electrophotographic photoreceptor of the present invention.

これを1試料Lとする。この試料1を1静電複写紙試験
装置SP−428型ョ(川口電機製作所製)に装着し、
帯電器放電極に対する印加電圧を一ひ■として5秒間帯
電操・作を行ない、この帯電操作直後における感光層表
面の帯電電位VO(V)及びこの帯電電位VOを112
に減衰せしめるために必要な半減露光量Ell2(Ix
.sec)とを測定した。
This is referred to as one sample L. This sample 1 was attached to an electrostatic copying paper tester SP-428 model (manufactured by Kawaguchi Electric Seisakusho),
A charging operation was performed for 5 seconds with the voltage applied to the discharge electrode of the charger set to 1, and the charging potential VO (V) on the surface of the photosensitive layer immediately after this charging operation and this charging potential VO were 112
The half-reduced exposure amount Ell2(Ix
.. sec) was measured.

結果は第1表に示す通りである。実施例2〜4 この各実施例においては、キャリア輸送物質として、例
示ヒドラゾン誘導体〔Pl)に代えて同〔P2〕,〔P
4〕及び同〔P9〕を用いたほかは、実施例1と同様に
して合計3種の本発明電子写真感光体を作製した。
The results are shown in Table 1. Examples 2 to 4 In each of these Examples, hydrazone derivatives [P2] and [Pl] were used instead of the exemplified hydrazone derivative [Pl] as carrier transport substances.
A total of three types of electrophotographic photoreceptors of the present invention were produced in the same manner as in Example 1, except that Samples No. 4] and P9 were used.

これらを1試料2J−1試料4Jとし、試料1と同様に
して各々の帯電電位VO及び半減露光量ElI2を測定
した。結果は第1表に示す通りである。RCTMョはキ
ャリア輸送物質、RCTLョはキャリア輸送層を示す。
These were designated as 1 sample 2J-1 sample 4J, and the charging potential VO and half-decreased exposure amount ElI2 of each were measured in the same manner as sample 1. The results are shown in Table 1. RCTM represents a carrier transport material, and RCTL represents a carrier transport layer.

実施例5〜7 この各実施例においては、キャリア発生物質として、例
示物質〔A2〕(アントアントロン系顔料1インダンス
レンプリリアントオレンジGKョC●■・NO.593
O5)、〔B3〕(ジベンズピレンキノン系顔料1イン
ダンスレンゴールデンイエローRKJC.I.NO59
lO5)及び〔C4〕(ピラントロン系顔料「パリオゲ
ンレツド33340J)を、それぞれ例示物質〔A3〕
の代りに用いたほかは、実施例1と同様にして厚さ0.
5ミクロンのキャリア発生層を形成し、キャリア輸送物
質として例示ヒドラゾン誘導体〔P1)を用いて実施例
1と同様にしてキャリア輸送層を形成し、以つて合計3
種の本発明電子写真感光体を作製し、これらを7試料5
ョ〜1試料7.Jとし、試料1と同様にして各々の帯電
電位VO及び半減露光量Ell2を測定した。
Examples 5 to 7 In each of these Examples, the carrier-generating substance was exemplified substance [A2] (Anthrone pigment 1 Indanthrene Priliant Orange GKyo C●■・NO.593
O5), [B3] (Dibenzpyrenequinone pigment 1 Indanthrene Golden Yellow RKJC.I.NO59
lO5) and [C4] (pyranthrone pigment "Paliogen Red 33340J), respectively, as exemplified substances [A3]
A thickness of 0.
A carrier generation layer of 5 microns was formed, and a carrier transport layer was formed in the same manner as in Example 1 using the exemplified hydrazone derivative [P1] as a carrier transport material, so that a total of 3 microns was formed.
Separate electrophotographic photoreceptors of the present invention were prepared, and these were divided into 7 samples and 5
1 sample 7. J, and in the same manner as Sample 1, each charging potential VO and half-decreased exposure amount Ell2 were measured.

結果は第2表に示す通りである。RCGMJはキャリア
発生物質を示す。
The results are shown in Table 2. RCGMJ indicates a carrier generating substance.

実施例8 厚さ100ミクロンのポリエチレンテレフタレートより
成る基体上にアルミニウムを蒸着して成る導電性支持体
に、塩化ビニルー酢酸ビニルー無水マレイン酸共重合体
1エスレツハE−10ョ(積水化学工業社製)より成る
厚さ約0.1ミクロンの中間層を設け、ポリカーボネー
ト樹脂3gを1,2−ジク山レエタン100m1中に溶
解した溶液にキャリア発生物質として例示物質〔A3〕
を3g加えて超音波分散を行なつて得られた分散液を、
前記中間層上にワイアーパー塗布法により塗布し乾燥し
て、厚さ2ミクロンのキャリア発生層を形成した。
Example 8 Vinyl chloride-vinyl acetate-maleic anhydride copolymer 1 Esletsuha E-10 (manufactured by Sekisui Chemical Co., Ltd.) was applied to a conductive support made by vapor-depositing aluminum on a substrate made of polyethylene terephthalate with a thickness of 100 microns. Example material [A3] is prepared as a carrier-generating substance in a solution of 3 g of polycarbonate resin dissolved in 100 ml of 1,2-dikuyama rhethane.
The dispersion obtained by adding 3g of and carrying out ultrasonic dispersion,
A carrier generation layer having a thickness of 2 microns was formed by coating on the intermediate layer by a wire spray coating method and drying.

このキャリア発生層上に、キャリア輸送物質として例示
ヒドラゾン誘導体〔Pll)を用いて実施例1と同様に
して厚さ10ミクロンのキャリア輸送層を形成し、以つ
て本発明電子写真感光体を作製した。
On this carrier generation layer, a carrier transport layer having a thickness of 10 microns was formed in the same manner as in Example 1 using an exemplary hydrazone derivative [Pll] as a carrier transport substance, thereby producing an electrophotographic photoreceptor of the present invention. .

これを1試料8Jとし、試料1と同様にして測定を行な
つたところ、VO=ー945(V)、Ell2=2.8
(Ix.sec)であつた。実施例9キャリア輸送物質
として例示ヒドラゾン誘導体〔P9〕を用い、その7.
5gとポリカーボネート樹脂10gとを1,2ージクロ
ルエタン100m1中に溶解し、ここに得られた溶液中
にキャリア発生物質として例示物質〔A3〕1.5gを
加えて超音波分散を行ない、この分散液を実施例8にお
けると同様の導電性支持体上に同様の中間層を設けたも
のに同様の方法て塗布した後、温度70℃で1時間乾燥
して厚さ13ミクロンの感光層を有する本発明電子写真
感光体を作製した。
When one sample was 8J and measurements were carried out in the same manner as sample 1, VO=-945 (V), Ell2=2.8
(Ix.sec). Example 9 Using an exemplary hydrazone derivative [P9] as a carrier transport substance, 7.
5g of polycarbonate resin and 10g of polycarbonate resin were dissolved in 100ml of 1,2-dichloroethane, 1.5g of exemplified substance [A3] was added as a carrier generating substance to the resulting solution, and ultrasonic dispersion was performed to obtain this dispersion. The same intermediate layer was provided on the same conductive support as in Example 8 and was coated by the same method and dried at a temperature of 70° C. for 1 hour to form a photosensitive layer of the present invention having a thickness of 13 microns. An electrophotographic photoreceptor was produced.

これを1試料9Jとする。試料9の感光層は、第5図に
示したようにキャリア輸送相31中にキャリア発生物質
21が分散された構造を有するものである。この試料9
について試料1と同様にして測定を行なつたところ、V
O=ー927(V)、Ell2=5.1(Ix●Sec
)であつた。
This is assumed to be 9J for one sample. The photosensitive layer of Sample 9 has a structure in which a carrier generating substance 21 is dispersed in a carrier transporting phase 31, as shown in FIG. This sample 9
When measurements were carried out in the same manner as for sample 1, V
O=-927(V), Ell2=5.1(Ix●Sec
).

以上の各実施例において得られた試料1〜試料9の各々
を電子複写機RU−BiX2OOORJ(小西六写真工
業社製)に装着して実写テストを行なつたところ、充分
な画像濃度を有し、且つカブリの無い良好な複写画像を
得ることができた。
When each of Samples 1 to 9 obtained in each of the above Examples was attached to an electronic copying machine RU-BiX2OOORJ (manufactured by Konishiroku Photo Industry Co., Ltd.) and a photocopying test was conducted, it was found that the image density was sufficient. , and a good copy image without fog could be obtained.

比較例1 キャリア発生物質としてクロルダイアンブルーを用い、
その0.5gを、エチレンジアミンとn−ブチルアミン
とテトラヒドロフランとより成りその重量比が1.2:
1.0:2.2の混合溶剤75g中に溶解し、この溶液
を実施例8におけると同様の導電性支持体上に乾燥後の
付着量が0.2g/dとなるよう塗布してキャリア発生
層を形成した。
Comparative Example 1 Chlordiane blue was used as a carrier generating substance,
0.5g of it was made of ethylenediamine, n-butylamine, and tetrahydrofuran, the weight ratio of which was 1.2:
A carrier was prepared by dissolving the solution in 75 g of a mixed solvent of 1.0:2.2 and coating it on the same conductive support as in Example 8 so that the amount of adhesion after drying was 0.2 g/d. A generation layer was formed.

このキャリア発生層上に、キャリア輸送物質として例示
ヒドラゾン誘導体〔P1)を用い実施例1と同様にして
厚さ10ミクロンのキャリア輸送層を形成し、以つて比
較用電子写真感光体を作製した。これを1比較試料しと
し、試料1と同様にして測定を行なつてところ、VO=
ー783(V)、Ell2=4.9(Ix.sec)と
本発明電子写真感光体に比して感度は小さいものであつ
た。比較例2 キャリア発生物質として、クロルダイアンブルーの代り
にメチルスカリリウムを用いたほかは比較例1と同様に
して電子写真感光体を作製した。
On this carrier generation layer, a carrier transport layer having a thickness of 10 microns was formed in the same manner as in Example 1 using the illustrated hydrazone derivative [P1] as a carrier transport substance, thereby producing a comparative electrophotographic photoreceptor. This was used as a comparison sample, and measurements were carried out in the same manner as sample 1, and VO=
-783 (V), Ell2 = 4.9 (Ix.sec), which was lower than the electrophotographic photoreceptor of the present invention. Comparative Example 2 An electrophotographic photoreceptor was produced in the same manner as Comparative Example 1, except that methylscalyllium was used instead of chlordian blue as a carrier generating substance.

これを1比較試料2Jとし、試料1と同様にして測定を
行なつたところ、■O=ー735(V)、Ell2−ニ
4.4(IX●Sec)であつた。以上から明らかなよ
うに、キャリア発生物質として本発明の化合物以外のも
のを用いた場合には、キャリア輸送物質として本発明で
用いられるヒドラゾン誘導体を用いたときにも、優れた
感度l特性を得ることができない。
This was used as 1 Comparative Sample 2J, and measurements were carried out in the same manner as Sample 1. As a result, ■O=-735 (V) and Ell2-ni 4.4 (IX●Sec). As is clear from the above, when a substance other than the compound of the present invention is used as a carrier-generating substance, excellent sensitivity characteristics can be obtained even when the hydrazone derivative used in the present invention is used as a carrier-transporting substance. I can't.

比較例3キャリア輸送物質として、例示ヒドラゾン誘導
体〔Pl)の代りに1,1−ビス(4−N,N−ジエチ
ルアミノー2−メチルフェニル)−1−フエニルメタン
を用いて厚さ11ミクロンのキャリア輸送層を形成した
ほかは実施例1と同様にして電子写真感光体を作製した
Comparative Example 3 Carrier transport with a thickness of 11 microns using 1,1-bis(4-N,N-diethylamino-2-methylphenyl)-1-phenylmethane instead of the exemplified hydrazone derivative [Pl] as a carrier transport material An electrophotographic photoreceptor was produced in the same manner as in Example 1 except that the layers were formed.

これを1比較試料2Jとし、試料1と同様にして測定を
行なつたところ、VO=ー638(V)、E1′2=2
.5(Ix−Sec)であつた。次に試料1及び比較試
料3の各々を電子複写機RU−BlX2OOORJに装
着して連続複写テストを行ない、露光絞り値2.5にお
ける感光層の画像地肌部の電位を1エレクトロスタティ
ックボルトメーター144D−1D型J(モンローエレ
クトロニクスインコーポレーテツド社製)を用いて測定
した。
When this was used as 1 comparative sample 2J and measurements were performed in the same manner as sample 1, VO = -638 (V), E1'2 = 2
.. 5 (Ix-Sec). Next, each of Sample 1 and Comparative Sample 3 was installed in an electronic copying machine RU-BlX2OOORJ, and a continuous copying test was carried out. The measurement was performed using 1D Model J (manufactured by Monroe Electronics Inc.).

結果は第3表に示す通りである。この第3表の結果から
判断されるように、比較試料3のように、キャリア輸送
物質として本発明のヒドラゾン誘導体でないアリールア
ルカン化合物を用いた場合には、キャリア発生物質が本
発明のものてあつても、繰り返し特性が劣つていること
が明らかである。
The results are shown in Table 3. As judged from the results in Table 3, when an arylalkane compound other than the hydrazone derivative of the present invention is used as a carrier transporting substance as in Comparative Sample 3, the carrier generating substance is similar to that of the present invention. However, it is clear that the repeatability is inferior.

即ち、多数回に亘る連続コピーによる画像地肌部の電位
の増加が著しく、得られた複写画像はカブリが大きくて
実用には供することのできないものであつた。比較例4
〜8 キャリア輸送物質として、例示ヒドラゾン誘導体〔P1
)の代りに下記のものを用いたほかは実施例1と同様に
して電子写真感光体1比較試料4ョ〜0比較試料9ョを
作製し、その各々について試料1と同様にして測定を行
なつた。
That is, the potential of the background portion of the image increases significantly due to continuous copying a large number of times, and the resulting copied image has a large amount of fog and cannot be put to practical use. Comparative example 4
~8 Exemplary hydrazone derivative [P1
) Electrophotographic photoreceptors 1 comparative sample 4 to 0 comparative sample 9 were prepared in the same manner as in Example 1, except that the following materials were used in place of Summer.

結果は第4表に示す通りである。比較試料4:N−エチ
ルカルバゾール 比較試料5:アントラセン 比較試料6:フルオレノン 比較試料7:2,4,7−トリニトロー9−フ
ルオレノン比較試料8:2,4,5,7−テトラニト
ロフ ルオレノン比較試料9:ポリビニルカル
バゾール 以上の結果、本発明において用いるキャリア発生物質を
用いたときにも、キャリア輸送物質が特定のものでない
ときには、大きな感度を有する電子写真感光体を得るこ
とができないことが明らかである。
The results are shown in Table 4. Comparative sample 4: N-ethylcarbazole Comparative sample 5: Anthracene Comparative sample 6: Fluorenone Comparative sample 7: 2,4,7-trinitro 9-fluorene
Fluorenone Comparative Sample 8: 2,4,5,7-Tetranitroph Fluorenone Comparative Sample 9: Polyvinylcarbazole As a result, even when the carrier-generating substance used in the present invention is used, when the carrier-transporting substance is not a specific one, a large It is clear that an electrophotographic photoreceptor with sensitivity cannot be obtained.

以上の説明から明らかなように、本発明において用いる
キャリア輸送物質を用いた場合であつてもキャリア発生
物質として本発明において用いるもの以外のキャリア発
生物質を用いたとき、並びに、本発明において用いるキ
ャリア発生物質を用いた場合であつてもキャリア輸送物
質として本発明において用いるもの以外のキャリア輸送
物質を用いたときには、得られる電子写真感光体はきわ
めて感度の低いものとなり、また十分な特性を得ること
ができない。
As is clear from the above explanation, even when the carrier transporting substance used in the present invention is used, when a carrier generating substance other than that used in the present invention is used as a carrier generating substance, and the carrier used in the present invention Even when a generating substance is used, if a carrier transporting substance other than that used in the present invention is used as a carrier transporting substance, the resulting electrophotographic photoreceptor will have extremely low sensitivity, and sufficient characteristics may not be obtained. I can't.

しかし本発明におけるように、特定のキャリア発生物質
と、特定のキャリア輸送物質とを組合せることにより、
従来においては予期し得ない高い感度を有する優れた電
子写真感光体を得ることができる。
However, as in the present invention, by combining a specific carrier-generating substance and a specific carrier-transporting substance,
It is possible to obtain an excellent electrophotographic photoreceptor having a high sensitivity that was previously unexpected.

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

第1図は本発明電子写真感光体の構成の一例を示す説明
用拡大断面図、第2図は導電性支持体の変形例を示す説
明用拡大断面図、第3図及び第4図はそれぞれ本発明の
他の構成例を示す説明用拡大断面図、第5図は本発明の
更に他の構成例を示す説明用拡大断面図である。 1・・・・・・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、21・・・・・・
キャリア発生物質、31・・・・・・キャリア輸送相。
FIG. 1 is an explanatory enlarged sectional view showing an example of the structure of the electrophotographic photoreceptor of the present invention, FIG. 2 is an explanatory enlarged sectional view showing a modified example of the conductive support, and FIGS. 3 and 4 are respectively FIG. 5 is an explanatory enlarged cross-sectional view showing still another example of the structure of the present invention. FIG. 1... Conductive support, 2... Carrier generation layer, 3... Carrier transport layer, 4...
・Photosensitive layer, 5...Intermediate layer, 21...
Carrier generating substance, 31...Carrier transport phase.

Claims (1)

【特許請求の範囲】 1 キャリア発生相とキャリア輸送相とを組合わせて成
る感光層を導電性支持体上に設けて成る電子写真感光体
において、前記キャリア発生相が、下記一般式〔A〕で
示されるアンドアントロン顔料、下記一般式〔B〕で示
されるジベンズピレンキノン顔料及び下記一般式〔C〕
で示されるピラントロン顔料から成る群から選んだ少な
くとも1種を主成分として含有し、且前記キャリア輸送
相が、下記一般式〔P〕で示されるヒドラゾン誘導体を
主成分として含有することを特徴とする電子写真感光体
。 一般式〔A〕 ▲数式、化学式、表等があります▼ 一般式〔B〕 ▲数式、化学式、表等があります▼ 一般式〔C〕 ▲数式、化学式、表等があります▼ (式中、Xはハロゲン原子、ニトロ基、シアノ基、アシ
ル基、又はカルボキシル基を表わし、nは0〜4の整数
を表わし、mは0〜6の整数を表わす。 )一般式〔P〕 ▲数式、化学式、表等があります▼ (式中、R_1はアルキル基フェニル基又はベンジル基
を、R_2はアルキル基、フェニル基又はベンジル基を
、R_3は水素原子又はアルキル基を、 R_4は水素原子又はアルキル基を、 R_5は水素原子又はアルコキシ基を、 R_6は水素原子、アルキル基又はアルコキシ基を、R
_7は水素原子又はアルキル基を、 R_8は水素原子、アルキル基、アルコキシ基、ジアル
キルアミノ基又は複素環基を、表わし、nはR_3が水
素原子である場合には1を、R_3がアルキル基である
場合には1又は0を、表わす。 )2 前記感光層は、前記キャリア発生相の層とキャリ
ア輸送相の層との積層体によつて構成されている特許請
求の範囲第1項記載の電子写真感光体。 3 前記感光層は、前記キャリア発生相がキャリア輸送
相中に分散された状態に構成されている特許請求の範囲
第1項記載の電子写真感光体。
[Scope of Claims] 1. An electrophotographic photoreceptor comprising a photosensitive layer comprising a combination of a carrier generation phase and a carrier transport phase provided on a conductive support, wherein the carrier generation phase has the following general formula [A] andanthrone pigment represented by the following general formula [B], and a dibenzpyrenequinone pigment represented by the following general formula [C]
The carrier transport phase contains as a main component at least one selected from the group consisting of pyranthrone pigments represented by the following, and the carrier transport phase contains a hydrazone derivative represented by the following general formula [P] as a main component. Electrophotographic photoreceptor. General formula [A] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ General formula [B] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ General formula [C] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, represents a halogen atom, a nitro group, a cyano group, an acyl group, or a carboxyl group, n represents an integer of 0 to 4, and m represents an integer of 0 to 6.) General formula [P] ▲ Numerical formula, chemical formula, There are tables etc.▼ (In the formula, R_1 is an alkyl group, phenyl group or benzyl group, R_2 is an alkyl group, phenyl group or benzyl group, R_3 is a hydrogen atom or an alkyl group, R_4 is a hydrogen atom or an alkyl group, R_5 is a hydrogen atom or an alkoxy group, R_6 is a hydrogen atom, an alkyl group, or an alkoxy group, R
_7 represents a hydrogen atom or an alkyl group, R_8 represents a hydrogen atom, an alkyl group, an alkoxy group, a dialkylamino group, or a heterocyclic group, n is 1 when R_3 is a hydrogen atom, and when R_3 is an alkyl group, In some cases, it represents 1 or 0. )2 The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer is constituted by a laminate of a layer of the carrier generation phase and a layer of the carrier transport phase. 3. The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer is configured such that the carrier generation phase is dispersed in a carrier transport phase.
JP55146240A 1980-10-21 1980-10-21 electrophotographic photoreceptor Expired JPS6059589B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP55146240A JPS6059589B2 (en) 1980-10-21 1980-10-21 electrophotographic photoreceptor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP55146240A JPS6059589B2 (en) 1980-10-21 1980-10-21 electrophotographic photoreceptor

Publications (2)

Publication Number Publication Date
JPS5770535A JPS5770535A (en) 1982-05-01
JPS6059589B2 true JPS6059589B2 (en) 1985-12-25

Family

ID=15403263

Family Applications (1)

Application Number Title Priority Date Filing Date
JP55146240A Expired JPS6059589B2 (en) 1980-10-21 1980-10-21 electrophotographic photoreceptor

Country Status (1)

Country Link
JP (1) JPS6059589B2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6295535A (en) * 1985-10-22 1987-05-02 Konishiroku Photo Ind Co Ltd Photosensitive body
JPH0754414B2 (en) * 1986-06-16 1995-06-07 富士ゼロックス株式会社 Electrophotography method

Also Published As

Publication number Publication date
JPS5770535A (en) 1982-05-01

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