JPH01280763A - Electrophotographic sensitive body - Google Patents

Electrophotographic sensitive body

Info

Publication number
JPH01280763A
JPH01280763A JP63247033A JP24703388A JPH01280763A JP H01280763 A JPH01280763 A JP H01280763A JP 63247033 A JP63247033 A JP 63247033A JP 24703388 A JP24703388 A JP 24703388A JP H01280763 A JPH01280763 A JP H01280763A
Authority
JP
Japan
Prior art keywords
photoreceptor
charge
group
layer
aminobiphenyl
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
JP63247033A
Other languages
Japanese (ja)
Other versions
JP2753582B2 (en
Inventor
Tomoyuki Shimada
知幸 島田
Masaomi Sasaki
正臣 佐々木
Mitsuru Hashimoto
充 橋本
Tamotsu Ariga
保 有賀
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
Publication of JPH01280763A publication Critical patent/JPH01280763A/en
Application granted granted Critical
Publication of JP2753582B2 publication Critical patent/JP2753582B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0601—Acyclic or carbocyclic compounds
    • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
    • G03G5/0614—Amines
    • G03G5/06142—Amines arylamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

PURPOSE:To improve photosensitive characteristics and to enhance the strength to heat and impact by providing a photosensitive layer contg. an aminobiphenyl compd. expressed by prescribed formula as an effective component on a conductive base. CONSTITUTION:The photosensitive body 2 contg. at least one kind of the compd. expressed by formula I [R<1>, R<2>, R<3> denote a hydrogen atom, amino group, alkoxy group, thioalkoxy group, aryloxy group, methylenedioxy group, substd. or unsubstd. alkyl group, halogen atom or substd. or unsubstd. aryl group; R<2> denotes a hydrogen atom, alkoxy group, substd. or unsubstd. alkyl group or halogen group, exclusive of the case in which all of R<1>-R<4> are the hydrogen atom; (k), l, m, n denote 1, 2, 3 or 4 integer and R<1>-R<4> may be the same as or different from each other when if each thereof is 2, 3, 4 integer] as the effective component is provided on the conductive base 1. This photosensitive body 2 has the excellent photosensitive characteristics and the improved durabil ity.

Description

【発明の詳細な説明】 〔技術分野〕 本発明は電子写真用感光体に関し、詳しくは感光層中に
特定の化合物を含有させた電子写真用感光体に関する。DETAILED DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor containing a specific compound in a photosensitive layer.

〔従来技術〕[Prior art]

従来、電子写真方式において使用きれる感光体の光導電
性素材として用いられているものにセレン、硫化力１く
ミウム、醸化」１１鉛などの無機物質がある。ここにい
う「電子写真方式」とは、一般に、光導電性の感光体を
まず暗所で、例えはコロナ放電によって帯電せしめ、次
いで像露光し、露光部のみの電荷を選択的に逸散せしめ
て静電潜像を得、この潜像部を染料、顔料などの着色材
と高分子物質などの結合剤とから構成される検電微粒子
（トナー）で現像し可視化して画像を形成するようにし
た画像形成法の一つである。Conventionally, inorganic materials such as selenium, sulfurized lead, and sulfurized lead have been used as photoconductive materials for photoreceptors that can be used in electrophotography. The "electrophotographic method" referred to here generally means that a photoconductive photoreceptor is first charged in a dark place, for example by corona discharge, and then imagewise exposed to selectively dissipate the charge only in the exposed areas. to obtain an electrostatic latent image, and this latent image area is developed and visualized with electrostatic fine particles (toner) consisting of a coloring material such as a dye or pigment and a binder such as a polymer substance to form an image. This is one of the most widely used image forming methods.

このような電子写真法において感光体に要求される基本
的な特性としては、（１）暗所で適当な電位に４（Ｆ電
できること、（２）暗所において電荷の逸散が少ないこ
と、（３）光照射によって速やかに電荷を逸散せしめう
ろことなどがあげられる。The basic characteristics required of a photoreceptor in such electrophotography are (1) ability to conduct 4F to an appropriate potential in a dark place, (2) low charge dissipation in a dark place, (3) Examples include scales that quickly dissipate charge when irradiated with light.

ところで、前記の無機物質はそれぞれが多くの長所をも
っていると同時に、さまさまな欠点をも有しているのが
実状である。例えば、現在広く用いられているセレンは
１）η記（１）〜（：３）の条件は十分に満足するが、
製造する条件がむすかしく、製造コス１〜が高くなり、
可撓性がなく、ベルト状に加工することがむずかしく、
熱や機械的の衝撃に縞敏なだめ取扱いに注意を要するな
どの欠点もある。Incidentally, the reality is that each of the above-mentioned inorganic substances has many advantages, but also has various disadvantages. For example, selenium, which is currently widely used, fully satisfies the conditions (1) to (3) in 1) η, but
The manufacturing conditions are difficult and the manufacturing cost is high,
It has no flexibility and is difficult to process into a belt shape.
It also has drawbacks such as being sensitive to heat and mechanical shock and requiring careful handling.

硫化力１−ミウムや酸化亜鉛は、結合剤としての樹脂に
分散させて感光体として用いられているが、平滑性、硬
度、引張り強度、耐摩擦性などの機械的な欠点があるた
めにそのままでは反復して使用することができない。Sulfidation power 1-mium and zinc oxide are used as photoreceptors by being dispersed in a resin as a binder, but they have mechanical drawbacks such as smoothness, hardness, tensile strength, and abrasion resistance, so they cannot be used as they are. cannot be used repeatedly.

近年、これら無機物質の欠点を排除するためにいろいろ
な有機物質を用いた電子写真用感光体が提案され、実用
に供されているものもある。例えば、ポリ−Ｎ−ビニル
カルバゾールと２．４．７−１−り二１−ロフルオレン
ー９−オンとからなる感光体（米国特許第３４８４２３
７号明細書に記載）、ポリ−Ｎ−ビニルカルバゾールを
ビリリウム塩系色索で増感してなる感光体（特公昭４８
−２５６５８号公報に記載）、有機顔料を主成分とする
感光体（特開昭４７−３７５４３号公報に記載）、染料
と樹脂とからなる共晶錯体を主成分とする感光体（特開
昭４７−１０７３５号公報に記載）、１〜リフ工ニルア
ミン化合物を色素増感してなる感光体（米国特許第３，
１８０，７３０号）、ポリ−Ｎ−ビニルカルバゾールと
アミン誘導体を電荷輸送材料として用いる感光体（特開
昭５８−１１５５号公報）などである。In recent years, electrophotographic photoreceptors using various organic materials have been proposed in order to eliminate the drawbacks of these inorganic materials, and some of them have been put into practical use. For example, a photoreceptor made of poly-N-vinylcarbazole and 2,4,7-1-di-21-rofluorene-9-one (U.S. Pat.
7), a photoreceptor made by sensitizing poly-N-vinylcarbazole with a biryllium salt-based color cord (Japanese Patent Publication No. 48
-25658), a photoreceptor whose main component is an organic pigment (described in JP-A-47-37543), a photoreceptor whose main component is a eutectic complex consisting of a dye and a resin (described in JP-A-47-37543), a photoreceptor whose main component is a eutectic complex consisting of a dye and a resin No. 47-10735), photoreceptors formed by dye-sensitizing 1-refined nylamine compounds (U.S. Pat. No. 3,
180,730), and a photoreceptor using poly-N-vinylcarbazole and an amine derivative as a charge transport material (Japanese Patent Laid-Open No. 1155/1983).

これらの感光体は優れた特性を有しており実用的にも価
値が高いと思オ）れるものであるが、電子写真法におい
て、感光体に対するいろいろな要求を考慮すると、まだ
、これらの要求を十分に満足するものが得られていない
のが実状である。また米国特許第３，２６５，４９６号
、特公昭３９−１１５４６号公報、特開昭５３−２７０
３３号公報に記載されている多官能第一３＝ ３アミン化合物、なかでもベンジジン系化合物が電子写
真感光体用の光導電月料として優れていることが知られ
ているが、これらの化合物は接着樹脂への溶解度が低く
感光層中で結晶化する問題がある。これを改良する為に
例えは特開昭６２−１１２１６４号公報では他の低分子
化合物と併用することにより結晶化をおさえる試みがな
されている。Although these photoreceptors have excellent properties and are considered to be of high practical value, considering the various requirements for photoreceptors in electrophotography, these requirements are still not met. The reality is that we have not yet obtained anything that fully satisfies these requirements. Also, U.S. Pat.
It is known that polyfunctional primary 3=3 amine compounds described in Publication No. 33, especially benzidine compounds, are excellent as photoconductive materials for electrophotographic photoreceptors. There is a problem that the solubility in the adhesive resin is low and crystallization occurs in the photosensitive layer. In order to improve this problem, for example, JP-A-62-112164 attempts to suppress crystallization by using it in combination with other low-molecular-weight compounds.

〔目　　的〕〔the purpose〕

本発明の１」的は、先に述べた従来の感光体のもつ種々
の欠点を解消し、電子写真法において要求される条件を
十分満足しうる感光体を提供することにある９、更に、
本発明の他の目的は、製造が容易でかつ比較的安価に行
なえ、耐久性にもすぐれた電子写真用感光体を提供する
ことに−ある。One object of the present invention is to provide a photoreceptor that can eliminate the various drawbacks of the conventional photoreceptor described above and fully satisfy the conditions required in electrophotography.
Another object of the present invention is to provide an electrophotographic photoreceptor that is easy to manufacture, relatively inexpensive, and has excellent durability.

〔構　　成〕〔composition〕

本発明によれば、導電性支持体上に下記一般式（Ｔ）で
表わされるアミノビフェニル化合物の少くとも１種を有
効成分として含有する感光Ｉ〜を有することを特徴とす
る電子写真用感光体が提供される。According to the present invention, an electrophotographic photoreceptor is provided with a photoreceptor I containing as an active ingredient at least one aminobiphenyl compound represented by the following general formula (T) on a conductive support. is provided.

＝４− （式中、Ｒ１、Ｒ３及びＲ４は水素原子、アミノ基、ア
ルコキシ基、チオアルコキシ基、アリールオキシ基、メ
チレンジオキシ基、置換もしくは無置換のアルキル基、
ハロゲン原子又は置換もしくは無置換のアリール基を、
Ｒ２は水素原子、アルコキシ基、置換もしくは無置換の
アルキル基又はハロゲンを表わす。但し、［（１、Ｒ２
、Ｒ１及びＲ４がすべて水素原子である場合は除く。ま
たｋ、Ｑ、ｍ及びｎは１．２．３又は４の整数であり、
各々が２．３又は４の整数の時は前記Ｒ１、］（２、Ｉ
＋３及び１く４は同一でも異なっていてもよい。） 本発明において感光層に含有させる前記一般式（１）で
表わされるアミノビフェニル化合物は、例えば一般式（
Ｈ） （式中、Ｒ１、Ｒ２、ｋ及びＱは荊と同じ。Ｘはハロゲ
ンを表わす。） で表わされるビフェニル化合物と一般式（ｌＩ［）（式
中、Ｒ３、［（４、ｍ及びｎは前記と同じ。）で表わさ
れるアミノ化合物を反応させることによって製造される
。=4- (wherein R1, R3 and R4 are hydrogen atoms, amino groups, alkoxy groups, thioalkoxy groups, aryloxy groups, methylenedioxy groups, substituted or unsubstituted alkyl groups,
A halogen atom or a substituted or unsubstituted aryl group,
R2 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group, or a halogen. However, [(1, R2
, except when R1 and R4 are all hydrogen atoms. Further, k, Q, m and n are integers of 1.2.3 or 4,
When each is an integer of 2.3 or 4, the above R1, ](2, I
+3 and 1-4 may be the same or different. ) In the present invention, the aminobiphenyl compound represented by the general formula (1) contained in the photosensitive layer is, for example, a compound represented by the general formula (
H) (In the formula, R1, R2, k and Q are the same as 荊. is the same as above.) is produced by reacting an amino compound represented by:

前記合成法で得られる一般式（１）で示されるアミノビ
フェニル化合物を以下に例示する。The aminobiphenyl compound represented by the general formula (1) obtained by the above synthesis method is illustrated below.

＝７− 本発明の感光体は、上記のようなアミノビフェニル化合
物の１種又は２種以」二を感光層２（２’　、２″、２
”’又は２ｒｔ／Ｌ）に含有させたものであるが、これ
らアミノビフェニル化合物の応用の仕方によって第１図
、第２図、第３図、第４図あるいは第５図に示したごと
くに用いることができる。=7- The photoreceptor of the present invention contains one or more of the above aminobiphenyl compounds in the photosensitive layer 2 (2', 2'', 2'').
Depending on the application of these aminobiphenyl compounds, they can be used as shown in Figure 1, Figure 2, Figure 3, Figure 4, or Figure 5. be able to.

第」図における感光体は導電性支持体１」二にアミノビ
フェニル化合物、増感染料および結合剤（結着樹脂）よ
りなる感光層２が設けられたものである。The photoreceptor shown in FIG. 1 has a conductive support 1 and a photosensitive layer 2 comprising an aminobiphenyl compound, a sensitizing dye, and a binder (binder resin).

ここでのアミノビフェニル化合物は光導電性物質として
作用し、光減衰に必要な電荷担体の生成および移動はア
ミノビフェニル化合物を介して行なわれる。しかしなが
ら、アミノビフェニル化合物は光の可視領域においてほ
とんど吸収を有していないので、可視光で画像を形成す
る目的のためには可視領域に吸収を有する増感染料を添
加して増感する必要がある。The aminobiphenyl compound here acts as a photoconductive substance, and the generation and transfer of charge carriers necessary for light attenuation take place via the aminobiphenyl compound. However, aminobiphenyl compounds have almost no absorption in the visible region of light, so in order to form images with visible light, it is necessary to sensitize them by adding a sensitizing dye that absorbs in the visible region. be.

第２図における感光体は、導電性支持体１」ユに電荷発
生物質３をアミノビフェニル化合物と結合剤とからなる
電荷搬送媒体４の中に分散せしめた感光層２′が設けら
れたものである。ここでのアミノビフェニル化合物は結
合剤（又は、結合剤及び可塑剤）とともに電荷搬送媒体
を形成し、一方、電荷発生物質３（無機又は有機顔料の
ような電荷発生物質）が電荷担体を発生する。この場合
、電荷搬送媒体４は主として電荷発生物質３が発生する
電荷担体を受入れ、これを搬送する作用を一担当してい
る。そして、この感光体にあっては電荷発生物質とアミ
ノビフェニル化合物とが、たがいに、主として可視領域
において吸収波長領域が重ならないというのが基本的条
件である。これは、電荷発生物質３に電荷担体を効率よ
く発生させるためには電荷発生物質表面まで、光を透過
させる必要があるからである。−数式（Ｉ）で表わされ
るアミノビフェニル化合物は可視領域にほとんど吸収が
なく、一般に可視領域の光線を吸収し、電荷担体を発生
する電荷発生物質３と組合わせた場合、特に有効に電荷
搬送物質として働くのがその特長である。The photoreceptor shown in FIG. 2 has a photosensitive layer 2' in which a charge generating substance 3 is dispersed in a charge transporting medium 4 made of an aminobiphenyl compound and a binder on a conductive support 1''. be. The aminobiphenyl compound here forms the charge transport medium together with the binder (or binder and plasticizer), while the charge generating substance 3 (charge generating substance such as an inorganic or organic pigment) generates the charge carriers. . In this case, the charge transport medium 4 is mainly responsible for receiving charge carriers generated by the charge generating substance 3 and transporting them. In this photoreceptor, the basic condition is that the absorption wavelength regions of the charge generating substance and the aminobiphenyl compound do not overlap each other, mainly in the visible region. This is because in order to efficiently generate charge carriers in the charge generation material 3, it is necessary to transmit light to the surface of the charge generation material. - The aminobiphenyl compound represented by the formula (I) has almost no absorption in the visible region, generally absorbs light in the visible region, and is particularly effective as a charge transport material when combined with the charge generating material 3 that generates charge carriers. Its feature is that it works as a.

第３図における感光体は、導電性支持体１上に電荷発生
物質３を主体とする電荷発生Ｊｆ４５と、アミノビフェ
ニル化合物を含有する電荷搬送層４との積層からなる感
光層２”が設けられたものである。The photoreceptor shown in FIG. 3 has a photosensitive layer 2'' formed of a laminated layer of a charge-generating Jf45 mainly composed of a charge-generating substance 3 and a charge-transporting layer 4 containing an aminobiphenyl compound on a conductive support 1. It is something that

この感光体では、電荷搬送ＷＪ４を透過した光が電荷発
生Ｍ５に到達し、その領域で電荷担体の発生が起こり、
一方、電荷搬送層４は電荷担体の注入を受け、その搬送
を行なうもので、光減衰に必要な電荷担体の発生は、電
荷発生物質３で行なわれ、また電荷担体の搬送は、電荷
搬送層４（主としてアミノビフェニル化合物が働く）で
行なわれる。こうした機構は第２図に示した感光体にお
いてした説明と同様である。In this photoreceptor, the light transmitted through the charge transport WJ4 reaches the charge generation M5, and charge carriers are generated in that region.
On the other hand, the charge carrier layer 4 receives charge carriers and transports them. The charge carriers necessary for light attenuation are generated by the charge generation substance 3, and the charge carriers are transported by the charge carrier layer 4. 4 (mainly an aminobiphenyl compound acts). This mechanism is similar to the explanation given for the photoreceptor shown in FIG.

第４図における感光体は第３図の電荷発生Ｍ５とアミノ
ビフェニル化合物を含有する電荷搬送層４の積層順を逆
にしたものであり、その電荷担体の発生及び搬送の機構
は上記の説明と同様にできる。The photoreceptor in FIG. 4 is obtained by reversing the stacking order of the charge generation M5 in FIG. 3 and the charge transport layer 4 containing an aminobiphenyl compound, and the mechanism of charge carrier generation and transport is the same as the above explanation. You can do the same.

この場合機械的強度を考慮し第５図の様に電荷発生層５
の」二に保護層６を設けることもできる。In this case, considering mechanical strength, the charge generation layer 5 is
A protective layer 6 can also be provided on the second side.

実際に本発明感光体を作製するには、第１図に示した感
光体であれば、結合剤を溶かした溶液にアミノビフェニ
ル化合物の］種又は２種以」二を溶解し、更にこれに増
感染料を加えた液をつくり、これを導電性支持体Ｌ１−
に塗布し乾燥して感光層２を形成すればよい。In order to actually produce the photoreceptor of the present invention, in the case of the photoreceptor shown in FIG. 1, one or more aminobiphenyl compounds are dissolved in a solution containing a binder, and then A liquid containing a sensitizing dye is prepared, and this is applied to the conductive support L1-.
The photosensitive layer 2 may be formed by coating and drying the photosensitive layer 2.

感光１〜の厚さは３〜５０μｍ、好ましくは５〜２０μ
ｍが適当である。感光層２に占めるアミノビフェニル化
合物の量は；３０〜７０重量％、好ましくは約５０重量
２であり、また、感光Ｎ２に占める増感染料の量は０．
１〜５重量２、好ましくは０．５〜３重ｆＡｚである。The thickness of photosensitive layer 1 is 3 to 50 μm, preferably 5 to 20 μm.
m is appropriate. The amount of the aminobiphenyl compound in the photosensitive layer 2 is 30 to 70% by weight, preferably about 50% by weight2, and the amount of the sensitizing dye in the photosensitive layer 2 is 0.
1 to 5 weight 2, preferably 0.5 to 3 weight fAz.

増感染料としては、ブリリアン１〜クリーン、ビクトリ
アブルー１）、メチルバイオレット、クリスタルバイオ
レット、アシッドバイオレット６Ｂのような１〜リアリ
ールメタン染料、ローダミンＩ３、ローダミン６Ｇ、ロ
ーダミンＧエキストラ、エオシンＳ、エリ１−ロシン、
ローズベンガル、フルオレセインのようなキサンチン染
料、メチレンブルーのようなチアジン染料、シアニンの
ようなシアニン染料、２．６−ジフェニル−４−（Ｎ　
、　Ｎ−ジメチルアミノフェニル）チアピリリウムバー
クロレート、ベンゾピリリウム塩（特公昭４８−２５６
５８号公報に記載）などのピリリウム染料などが挙げら
れる。なお、これらの増感染料はｊ４１独で用いられて
も２種以上が併用されてもよい。The sensitizers include Brillian 1~Clean, Victoria Blue 1), 1~Rearylmethane dyes such as methyl violet, crystal violet, acid violet 6B, Rhodamine I3, Rhodamine 6G, Rhodamine G Extra, Eosin S, Eri 1). -Rosin,
Rose Bengal, xanthine dyes such as fluorescein, thiazine dyes such as methylene blue, cyanine dyes such as cyanine, 2,6-diphenyl-4-(N
, N-dimethylaminophenyl) thiapyrylium verchlorate, benzopyrylium salt (Japanese Patent Publication No. 48-256
Examples include pyrylium dyes such as those described in Japanese Patent No. 58). Note that these sensitizing agents may be used alone or in combination of two or more.

また、第２図に示した感光体を作製するには、１種又は
２種以−にのアミノビフェニル化合物と結合剤とを溶解
した溶液に電荷発生物質３の微粒子を分散せしめ、これ
を導電性支持体１上に塗布し乾燥して感光Ｍ２’を形成
すればよい。In addition, in order to produce the photoreceptor shown in FIG. 2, fine particles of the charge generating substance 3 are dispersed in a solution containing one or more aminobiphenyl compounds and a binder, and the particles are made conductive. The photosensitive material M2' may be formed by coating the photosensitive material onto the photosensitive support 1 and drying it.

感光層２′の厚さは３〜５０μｍ、好ましくは５〜２０
μｍが適当である。感光層２′に占めるアミノビフェニ
ル化合物の量は１０〜９５重量％、好ましくは３０〜９
０重量％であり、また、感光層２′に占める電荷発生物
質３の量は０，１〜５０重量２、好ましくは１〜２０重
＃、％である。電荷発生物質３としては、例えばセレン
、−】５− セレン−テルル、硫化カドミウム、硫化カドミウム−セ
レン、α−シリコンなどの無機顔料、有機顔料としては
例えばシーアイピグメン１〜ブルー２５（カラーインデ
ックスＣＩ　２１１８０）、シーアイピグメントレッＦ
４１（ＣＩ２１２００）、シーアイアシッドレッド５２
　（Ｃ１，’　４５１００）、シーアイベーシックレッ
ド３（ＣＩ４５２１０）、カルバゾール骨格を有するア
ゾ顔料（特開昭５３−９５０３３号公報に記載）、ジス
チリルベンゼン骨格を有するアゾ顔料（特開昭５３−１
３３４４５号公報）、１〜リフエニルアミン骨格を有す
るアゾ顔料（特開昭５３−１３２３４７号公報に記載）
、ジベンゾチオフェン骨格を有するアゾ顔料（特開昭５
４−２１７２８号公報に記載）、オキサジアゾール骨格
を有するアゾ顔料（特開昭５４−１２７４２号公報に記
載）、フルオレノン骨格を有するアゾ顔料（特開昭５４
−２２８３４号公報に記載）、ビススチルベン骨格を有
するアゾ顔料（特開昭５４−１７７３３号公報に記載）
、ジスチリルオキサジアゾール骨格を有するアゾ顔料（
特開昭５４−２１２９号公報に記載）、ジスチリルカル
バゾール骨格を有するアゾ顔料（特開昭５４−１４９６
７号公報に記載）などのアゾ顔料、例えばシーアイピグ
メン１〜ブルー１６（ＣＩ　７４１００）などのフタロ
シアニン系度ｆ料、例えばシーアイバラ１−ブラウン５
（ＣＩ　７３４］、０）、シーアイバットダイ（ＣＩ　
７３０３０）などのインジゴ系顔料、アルゴスカーレッ
１〜Ｂ（バイエル社製）、インダンスレンスカーレット
Ｒ（バイエル社製）などのペリレン系顔料などが挙げら
れる。なお、これらの電荷発生物質は単独で用いられて
も２種以上が併用されてもよい。The thickness of the photosensitive layer 2' is 3 to 50 μm, preferably 5 to 20 μm.
μm is appropriate. The amount of the aminobiphenyl compound in the photosensitive layer 2' is 10 to 95% by weight, preferably 30 to 9% by weight.
The amount of the charge generating substance 3 in the photosensitive layer 2' is 0.1 to 50% by weight, preferably 1 to 20% by weight. Examples of the charge generating substance 3 include inorganic pigments such as selenium, -]5-selenium-tellurium, cadmium sulfide, cadmium-selenium sulfide, and α-silicon; examples of organic pigments include C.I. Pigmen 1 to Blue 25 (color index CI 21180), CI Pigmentore F
41 (CI21200), Sea Eye Acid Red 52
(C1, '45100), CI Basic Red 3 (CI45210), an azo pigment having a carbazole skeleton (described in JP-A-53-95033), an azo pigment having a distyrylbenzene skeleton (JP-A-53-1
33445), 1 to azo pigments having a rifenylamine skeleton (described in JP-A-53-132347)
, an azo pigment having a dibenzothiophene skeleton (Japanese Unexamined Patent Publication No. 5
4-21728), azo pigments having an oxadiazole skeleton (described in JP-A-54-12742), azo pigments having a fluorenone skeleton (described in JP-A-54-12742),
-22834), an azo pigment having a bisstilbene skeleton (described in JP-A-54-17733)
, an azo pigment with a distyryloxadiazole skeleton (
(described in JP-A No. 54-2129), azo pigments having a distyrylcarbazole skeleton (described in JP-A-54-1496)
Azo pigments such as C.I. Pigmen 1 to Blue 16 (CI 74100), such as C.I. Pigmen 1 to Blue 16 (CI 74100), e.g.
(CI 734], 0), Sea Eye Bat Die (CI
73030), and perylene pigments such as Argo Scarlet 1 to B (manufactured by Bayer) and Indanthrene Scarlet R (manufactured by Bayer). Note that these charge generating substances may be used alone or in combination of two or more types.

更しこ、第３図に示した感光体は作製するには、導電性
支持体１以上に電荷発生物質を真空蒸着するか或いは、
電荷発生物質の微粒子３を必要によって結合剤を溶解し
た適当な溶媒中に分散した分散液を塗布し乾燥するかし
て、更に必要であればパフ研磨などの方法によって表面
仕上げ、膜厚調整などを行って電荷発生層５を形成し、
この上に１種又は２種以上のアミノビフェニル化合物と
結合剤とを溶解した溶液を塗布し乾燥して電荷搬送層４
を形成すればよい。なお、ここで電荷発生層５の形成に
用いられる電荷発生物質は前記の感光層２′の説明にお
いてしたのと同しものである。Furthermore, in order to produce the photoreceptor shown in FIG. 3, a charge-generating substance is vacuum-deposited on one or more conductive supports, or
A dispersion of the fine particles 3 of the charge-generating substance in a suitable solvent with a binder dissolved therein is coated and dried, and if necessary, the surface is finished by a method such as puff polishing, and the film thickness is adjusted. to form a charge generation layer 5,
A solution containing one or more aminobiphenyl compounds and a binder is applied thereon and dried to form a charge transport layer 4.
All you have to do is form. The charge generating material used to form the charge generating layer 5 is the same as that used in the description of the photosensitive layer 2'.

電荷発生層５の厚さは５μｍ以下、好ましくは２μｍ以
下であり、電荷搬送層４の厚さは３〜５０μｍ、好まし
くは５〜２０μｍが適当である。電荷発生Ｍ５が電荷発
生層物質の微粒子３を結合剤中に分散させたタイプのも
のにあっては、電荷発生物質の微粒子３の電荷発生層５
に占める割合は１０〜９５重量％、好ましくは５０〜９
０重量２程度である。また、電荷搬送層４に占める化合
物の量は１０〜９５重量ぶ、好ましくは３０〜９０重量
％である。第４図に示した感光体を作成するには、導電
性支持体１上にアミノビフェニル化合物と結合剤とを溶
解した溶液を塗布し、乾燥して電荷搬送層４を形成した
のち、この電荷搬送Ｊ−の上に電荷発生層物質の微粒子
を、必要によって結合剤を溶解した溶媒中に分散した分
散液をスプレー塗工等の方法で塗布乾燥して電荷発生層
５を形成すればよい。電荷発生Ｊ〜あるいは電荷搬送層
の量比は第３図で説明した内容と同様である。The thickness of the charge generation layer 5 is 5 μm or less, preferably 2 μm or less, and the thickness of the charge transport layer 4 is suitably 3 to 50 μm, preferably 5 to 20 μm. If the charge generation M5 is of a type in which fine particles 3 of a charge generation layer material are dispersed in a binder, the charge generation layer 5 of fine particles 3 of a charge generation material is
The proportion is 10 to 95% by weight, preferably 50 to 9% by weight.
0 weight is about 2. The amount of the compound in the charge transport layer 4 is 10 to 95% by weight, preferably 30 to 90% by weight. To produce the photoreceptor shown in FIG. 4, a solution containing an aminobiphenyl compound and a binder is applied onto the conductive support 1 and dried to form the charge transport layer 4. The charge generation layer 5 may be formed by applying a dispersion of fine particles of the charge generation layer material in a solvent in which a binder is dissolved, if necessary, on the carrier J- by a method such as spray coating and drying. The amount ratio of the charge generation J~ or the charge transport layer is the same as that explained with reference to FIG.

このようにして得られた感光体の電荷発生層５の」二に
更に適当な樹脂溶液をスプレー塗工等の方法により保護
Ｍ６を形成することにより第５図に示す感光体を作成で
きる。ここで用いる樹脂としては、後記する結合剤が使
用できる。The photoreceptor shown in FIG. 5 can be prepared by forming a protective layer M6 on the charge generating layer 5 of the photoreceptor thus obtained by spray coating or the like with a suitable resin solution. As the resin used here, the binder described later can be used.

なお、これらのいずれの感光体製造においては導電性支
持体１に、アルミニウムなどの金属板又は金属箔、アル
ミニウムなどの金属を蒸着したプラスチックフィル１１
、あるいは導電処理を施した紙などが用いられる。また
、結合剤としては、ポリアミ１く、ポリウレタン、ポリ
エステル、エポキシ樹脂、ポリケ１−ン、ポリカーボネ
ートなどの縮合樹脂や、ポリビニルケトン、ポリスチレ
ン、ポリ−Ｎ−ビニルカルバゾール、ポリアクリルアミ
ドのようなビニル重合体などが用いられるが、絶縁性で
かつ接着性のある樹脂はすべて使用できる。In the production of any of these photoreceptors, a metal plate or metal foil such as aluminum or a plastic film 11 on which metal such as aluminum is vapor-deposited is used on the conductive support 1.
Alternatively, paper that has been subjected to conductive treatment may be used. In addition, as a binder, condensation resins such as polyamide, polyurethane, polyester, epoxy resin, polycarbonate, and vinyl polymers such as polyvinyl ketone, polystyrene, poly-N-vinylcarbazole, and polyacrylamide can be used. However, any insulating and adhesive resin can be used.

必要により可塑剤が結合剤に加えられてるが、そうした
可塑剤としてはハロゲン化パラフィン、ポリ塩化ビフェ
ニル、ジメチルナフタリン、ジブチルフタレ−１〜など
が例示できる。A plasticizer is added to the binder if necessary, and examples of such plasticizers include halogenated paraffins, polychlorinated biphenyls, dimethylnaphthalene, and dibutyl phthalate.

更に、以」二のようにして得られる感光体には、導電性
支持体と感光層の間に、必要に応じて接着ＪＦＩ又はバ
リヤ層を設けることができる。これらの層に用いられる
材料としては、ポリアミド、ニトロセルロース、酸化ア
ルミニウムなどであり、また膜厚は１μｍ以下が好まし
い。Furthermore, in the photoreceptor obtained as described below, an adhesive JFI or barrier layer can be provided between the conductive support and the photosensitive layer, if necessary. Materials used for these layers include polyamide, nitrocellulose, aluminum oxide, etc., and the film thickness is preferably 1 μm or less.

本発明の感光体を用いて複写を行なうには、感光面に帯
電、露光を施した後、現像を行ない、必要によって、紙
などへ転写を行なう。本発明の感光体は感度が高く、ま
た可撓性に富むなどの優れた利点を有している。To make a copy using the photoreceptor of the present invention, the photoreceptor surface is charged and exposed, then developed and, if necessary, transferred to paper or the like. The photoreceptor of the present invention has excellent advantages such as high sensitivity and flexibility.

〔実施例〕〔Example〕

以下、実施例により本発明を説明する。なお、下記実施
例において部はすべて重量部である。。The present invention will be explained below with reference to Examples. In addition, in the following examples, all parts are parts by weight. .

〔−・数式（Ｔ）の化合物の合成〕[--Synthesis of compound of formula (T)]

（化合物Ｎｏ、２１の合成例） ４−メチル−４′−ヨードビフェニル３．３８ｇ、４、
．４　’　−ジ！〜リルアミン２．２１ｇ、炭酸カリウ
ム１．６７　ｇ及び銅粉５０ｍｇを二Ｉ−口ベンゼン５
０ｍ　Ｑに採り窒素気流下、エステル管で共線脱水しな
がら２０５〜２０８℃で１１時間かきまぜた。室温迄放
冷した後セライ１−を用いて濾過し、濾液に多景の水を
加え減圧下でニ＝２０− トロベンゼンを留去した後、残渣を１〜ルエンで抽出、
水洗、乾燥、濃縮して暗褐色の油状物を得た。(Synthesis example of compound No. 21) 4-methyl-4'-iodobiphenyl 3.38 g, 4,
．． 4'-ji! ~2.21 g of lylamine, 1.67 g of potassium carbonate, and 50 mg of copper powder were mixed with 2.5 g of benzene.
The mixture was taken in a 0mQ chamber and stirred at 205 to 208°C for 11 hours under a nitrogen stream while collinear dehydration was performed using an ester tube. After cooling to room temperature, it was filtered using CELAI 1-CELAI, and after adding Tasho water to the filtrate and distilling off the 20-trobenzene under reduced pressure, the residue was extracted with 1- toluene.
Washing with water, drying, and concentration gave a dark brown oil.

これを、クロマ１〜処理を２回行なった（シリカゲル、
溶離液；１回目トルエン、２回目トルエンー〇−ヘキサ
ン混合溶媒）後エタノールから再結晶して化合物Ｎ住２
１で表わされる４−メチル−４’−Ｎ、Ｎ−ビス（４−
メチルフェニル）アミノビフェニルの無色針状結晶２．
０８ｇ（収率５２％）を得た。This was subjected to Chroma 1 to 2 treatments (silica gel,
Eluent: first toluene, second toluene-hexane mixed solvent) and then recrystallized from ethanol to obtain compound N2.
4-methyl-4'-N,N-bis(4-
Colorless needle-shaped crystals of aminobiphenyl (methylphenyl)2.
08g (yield 52%) was obtained.

融点１１８．０〜１１９．０℃ 元素分析値（％）はＣ２７Ｈ２５Ｎとして下記の通りで
あった。Melting point: 118.0-119.0°C Elemental analysis values (%) as C27H25N were as follows.

ＣＨＮ 実測値　８８．９７　　６．８４　　３．６５削算値　
８９．２１　　６．９３　　３．８６実施例１ 電荷発生物質としてダイアンブルー（シーアイピグメン
１〜ブルー２５、ＣＩ　２］、１８０）７６部、ポリエ
ステル樹脂（バイロン２００、■東洋紡績製）の２％テ
Ｉ・ラヒドロフラン溶液１２６０部およびテ１−ラヒド
ロフラン３７００部をボールミル中で粉砕混合し、得ら
れた分散液をアルミニウム蒸着したポリエステルベ−ス
よりなる導電性支持体のアルミニラ１１面上にドクター
ブレー１くを用いて塗布し、自然乾燥してＪすさ約１μ
ｍの電荷発生層を形成した。CHN Actual value 88.97 6.84 3.65 reduced value
89.21 6.93 3.86 Example 1 76 parts of Diane Blue (CI Pigmen 1 to Blue 25, CI 2], 180) as a charge generating substance, 2% of polyester resin (Vylon 200, manufactured by Toyobo Co., Ltd.) 1,260 parts of the TeI-rahydrofuran solution and 3,700 parts of the Tei-rahydrofuran solution were pulverized and mixed in a ball mill, and the resulting dispersion was placed on the 11th aluminium surface of a conductive support made of aluminum-deposited polyester base with a doctor blade. Apply with a cloth and dry naturally to a thickness of approximately 1 μm.
A charge generation layer of m was formed.

一方、電荷搬送物質としてはＮｏ、２］のアミノビフェ
ニル化合物２部、ポリカーボネート樹脂（パンライ１へ
Ｋ１．３００．■帯広製）２部およびテ１〜ラヒドロフ
ラン１６部を混合溶解して溶液とした後、これを前記電
荷発生ＪＧ上にドクターブレードを用いて塗布し、８０
℃で２分間、ついて１２０°Ｃで５分間乾燥して厚さ約
２０μｍの電荷搬送層を形成せしめて感光体Ｎｏ、］を
作成した。On the other hand, as a charge transport substance, 2 parts of the aminobiphenyl compound No. 2], 2 parts of polycarbonate resin (K1.300 to Panrai 1, manufactured by Obihiro), and 16 parts of Te 1 to Lahydrofuran were mixed and dissolved to form a solution. , apply this onto the charge generation JG using a doctor blade, and
It was dried at 120° C. for 2 minutes and then for 5 minutes at 120° C. to form a charge transport layer with a thickness of about 20 μm, thereby producing photoreceptor No.

実施例２〜２７ 電荷発生物質および電荷搬送物質ポリオレフィン化合物
）を表−１に示したものに代えた以外は実施例１とまっ
たく同様にして感光体Ｎｏ、２〜２７を作成した。Examples 2 to 27 Photoreceptors Nos. 2 to 27 were prepared in exactly the same manner as in Example 1, except that the charge generating substance and the charge transporting substance (polyolefin compound) were replaced with those shown in Table 1.

実施例５２ 厚さ約３００μｍのアルミニウム板上にセレンを厚さ約
１μｍに真空蒸着して電荷発生層を形成せしめた。次い
でＮｏ、２１のアミノビフェニル化合物２部、ポリエス
テル樹脂（テユポン社製ポリエステルア１〜ヒーシブ４
９０００）３部およびテ１−ラヒ１くロワラン４５部を
混合、溶解して電荷搬送層形成液をつくり、これを上記
の電荷発生層（セレン蒸着層）上にドクタープレー１く
を用いて塗布し、自然乾燥した後、減圧下で乾燥して厚
さ約１０μｍの電荷搬送層を形成せしめて、本発明の感
光体Ｎｏ、５２を得た。Example 52 A charge generation layer was formed by vacuum-depositing selenium to a thickness of about 1 μm on an aluminum plate having a thickness of about 300 μm. Next, 2 parts of aminobiphenyl compound No. 21, polyester resin (Polyester A 1 to Hesive 4 manufactured by Teyupon)
Mix and dissolve 3 parts of 9000) and 45 parts of Te1-Rahi1-Rowaran to prepare a charge transport layer forming liquid, and apply this onto the above charge generation layer (selenium vapor deposited layer) using a doctor sprayer. After air drying, a charge transport layer having a thickness of about 10 μm was formed by drying under reduced pressure to obtain photoreceptor No. 52 of the present invention.

実施例５３ セレンの代りにペリレン系顔料 を用いて電荷発生ＭＣ但し、厚さは約０．６μｌ１ｌ）
を形成した、かつ電荷搬送物質としてアミノビフェニル
化合物Ｎα２１を用いた以外は実施例５２とまったく同
様にして感光体Ｎｏ、５３を作成した。Example 53 Charge generation MC using perylene pigment instead of selenium (However, the thickness is approximately 0.6 μl 1 liter)
Photoreceptor No. 53 was prepared in exactly the same manner as in Example 52, except that the aminobiphenyl compound Nα21 was used as the charge transport material.

実施例５４ ダイアンブルー（実施例１で用いたものと同じ）１部に
テＩ−ラヒドロフラン１５８部を加えた混合物をボール
ミル中で粉砕、混合した後、これにＮｏ、２１のアミノ
ビフェニル化合物１２部、ポリエステル樹脂（デュポン
社製ポリエステルア］くヒーシブ４９０００）１８部を
加えて、さらに混合して得た感光層形成液を、アルミニ
ウム蒸着ポリエステルフィルム−ににドクターブレード
を用いて塗布し、１００℃で３０分間乾燥して厚さ約１
６μｍの感光層を形成せしめて、本発明の感光体Ｎｏ　
、　５４を作成した。Example 54 A mixture of 1 part of Diane Blue (same as that used in Example 1) and 158 parts of TeI-Rahydrofuran was ground and mixed in a ball mill, and then 12 parts of aminobiphenyl compound No. 21 was added thereto. , 18 parts of polyester resin (Polyester Aheathysive 49000 manufactured by DuPont) was added, and the photosensitive layer forming solution obtained by further mixing was applied onto an aluminum-deposited polyester film using a doctor blade and heated at 100°C. Dry for 30 minutes to a thickness of approx.
A photosensitive layer of the present invention was formed by forming a photosensitive layer of 6 μm.
, 54 were created.

実施例５５ アルミニウム蒸着したポリエステルフィル１１基板上に
、実施例１で用いた電荷搬送層塗工液を実施例Ｉと同様
にしてブレード塗工し、ついで乾燥して厚さ約２０μｍ
の電荷搬送層を形成した。ビスアゾ顔料（Ｐ−２）１３
．５部、ポリビニルブチラール（商品名：ＸＹＩ比ユニ
オンカーバイ１−プラスチック社製）５．４部、ＴＩＩ
Ｆ　６８０部及びエチルセロソルブ１０２０部をボール
ミル中で粉砕混合した後、エチルセロソルブ１７００部
を加え攪拌混合して電荷発生層用塗工液を得た。この塗
工液を上記の電荷搬送層の上にスプレー塗工し、１００
℃で１０分間乾燥して厚さ約０．２μｍの電荷発生層を
形成した。さらにこの電荷発生層の上にポリアミド樹脂
（商品名：ＣＭ−８０００、東し製）のメタノール／ｎ
−ブタノール溶液をスプレー塗工し１．２０°Ｃで３０
分間乾燥して厚さ約０．５μｍの保護層を形成せしめて
感光体Ｎｏ、５５を作成した。Example 55 The charge transport layer coating solution used in Example 1 was applied with a blade onto an aluminum vapor-deposited polyester film 11 substrate in the same manner as in Example I, and then dried to a thickness of about 20 μm.
A charge transport layer was formed. Bisazo pigment (P-2) 13
．． 5 parts, polyvinyl butyral (trade name: XYI ratio Union Carby 1-manufactured by Plastics Co., Ltd.) 5.4 parts, TII
After pulverizing and mixing 680 parts of F and 1020 parts of ethyl cellosolve in a ball mill, 1700 parts of ethyl cellosolve was added and mixed with stirring to obtain a charge generation layer coating liquid. This coating solution was spray coated on the above charge transport layer, and
It was dried at .degree. C. for 10 minutes to form a charge generation layer with a thickness of about 0.2 .mu.m. Furthermore, on this charge generation layer, methanol/n of polyamide resin (product name: CM-8000, manufactured by Toshi) was applied.
- spray coating with butanol solution at 1.20 °C for 30
A protective layer having a thickness of about 0.5 μm was formed by drying for a minute to prepare photoreceptor No. 55.

かくしてつくられた感光体Ｎ０１１〜５５について、市
販の静４工複写紙試験装置（にに用１１電機製作所製Ｓ
Ｐ４２８型）を用いて一６ＫＶ又は＋６ＫＶのコロナ放
電を２０秒間行って帯電せしめた後、２０秒間暗所に放
置し、その時の表面電位Ｖｐｏ（ポル１−）を測定し、
ついでタングステンランプ光を、感光体表面の照度が４
．５ルツクスになるよう照射してその表面電位がｖｐｏ
の１７２になる迄の時間（秒）を求め、露光量Ｅ１／２
（ルックス・秒）を算出した。その結果を表−２に４示
す。Photoreceptors N011-55 thus produced were tested using a commercially available static copying paper tester (Niniyo 11 Denki Seisakusho S).
P428 type) was used to perform a corona discharge of 16 KV or +6 KV for 20 seconds to charge it, then leave it in a dark place for 20 seconds, and measure the surface potential Vpo (Pol 1-) at that time.
Next, the tungsten lamp light was applied to the surface of the photoreceptor at an illuminance of 4.
．． 5 lux, and the surface potential is vpo
Find the time (seconds) until it reaches 172, and calculate the exposure amount E1/2.
(looks/seconds) was calculated. The results are shown in Table 2.

また、以上の各感光体を市販の電子写真複写機を用して
帯電せしめた後、原図を介して光照射を行って静電潜像
製形成せしめ、乾式現像剤を用いて現像し、得られた画
像（１−ナー画像）を普通紙上に静電転写し、定着した
ところ、鮮明な転写画像が得られた。現像剤として湿式
現像剤を用いた場合も同様に鮮明な転写画像がネ；１・
られた。Further, each of the photoreceptors described above is charged using a commercially available electrophotographic copying machine, and then light is irradiated through the original image to form an electrostatic latent image, which is developed using a dry developer. When the resulting image (1-toner image) was electrostatically transferred onto plain paper and fixed, a clear transferred image was obtained. Even when a wet developer is used as the developer, a similarly clear transferred image can be obtained; 1.
It was done.

比較例１ 電荷発生物質としてＰ−２を、電荷搬送物質としてＮ、
Ｎ−ジフェニル−（１，１，’ビフェニルツー４−アミ
ン（比較感光体Ａ）及び４．４’　、４″−１〜リメチ
ル１〜リフエニルアミン（比較感光体Ｂ）を用いる以外
は実施例１と同様にして感光体を作成し、その感光体特
性を測定しＶｐｏ及びＥ１／２を算出した。また他の特
性として、露光開始後３０秒後の表面電位（Ｖｒとする
）も測定した。結果を本件の感光体Ｎα５とともに表−
３に示す。Comparative Example 1 P-2 was used as a charge generating substance, N was used as a charge transporting substance,
Examples except that N-diphenyl-(1,1,'biphenyl2-4-amine (comparative photoreceptor A) and 4,4',4''-1~limethyl 1~rifenylamine (comparative photoreceptor B) are used. A photoreceptor was prepared in the same manner as in 1, and its photoreceptor characteristics were measured to calculate Vpo and E1/2.As other characteristics, the surface potential (referred to as Vr) 30 seconds after the start of exposure was also measured. .The results are shown together with the photoconductor Nα5 of this case.
Shown in 3.

表−３ また、感光体Ｎα５と比較感光体へのくり返し疲労特性
を知るために−７，５ＫＶでの帯電と３０ルツクスでの
露光をくり返して、残留表面電位Ｖｒ’の変化を測定し
た。結果を第６図に示した。Table 3 In addition, in order to determine the repeated fatigue characteristics of the photoconductor Nα5 and the comparative photoconductor, charging at -7.5 KV and exposure at 30 lux were repeated, and changes in the residual surface potential Vr' were measured. The results are shown in Figure 6.

以上衣−３及び第６図より本発明の感光体Ｎα５に比べ
比較感光体Ａは電子写真感度（Ｅｌ／２）が低く疲労に
よる残留電位（Ｖｒ’）の上昇が認められた。また比較
感光体Ｂは同様に感度（Ｅｌ／２）が低く、初期特性に
おいて高い残留電位（Ｖｒ）を示すことがわかる。As shown in Figure 3 and Figure 6 above, comparative photoreceptor A had lower electrophotographic sensitivity (El/2) than photoreceptor Nα5 of the present invention, and an increase in residual potential (Vr') due to fatigue was observed. It can also be seen that comparative photoreceptor B has similarly low sensitivity (El/2) and exhibits a high residual potential (Vr) in its initial characteristics.

比較例２ 電子発生物質としてＰ−２を、電荷輸送物質としてＮ、
Ｎ−ジエチル−Ｎ’、Ｎ’−ビス（４−メチルフェニル
）−（ｔ、ｉ’−ビフェニル）−４，４’−ジアミンを
用いる以外は実施例１と同様にして感光体を作成した（
比較感光体Ｃ）。−７，５ＫＶでの帯電と３０Ｑｕｘで
の露光をくり返してＶｐｏ（ｖ）の変化を測定した。結
果を第７図に示した。第７図より本発明の感光体Ｎα５
に比べ疲労によるＶｐｏの著しい低下が認められる。Comparative Example 2 P-2 was used as the electron-generating substance, N was used as the charge-transporting substance,
A photoreceptor was prepared in the same manner as in Example 1 except for using N-diethyl-N',N'-bis(4-methylphenyl)-(t,i'-biphenyl)-4,4'-diamine (
Comparative photoreceptor C). Charging at -7.5 KV and exposure at 30 Qux were repeated to measure changes in Vpo (v). The results are shown in Figure 7. From FIG. 7, the photoreceptor Nα5 of the present invention
Compared to this, a significant decrease in Vpo due to fatigue was observed.

〔効　　果〕〔effect〕

本発明の感光体は感光特性に優れていることは勿論のこ
と、熱や機械的の衝撃に対する強度が大で、しかも安価
に製造することができる。The photoreceptor of the present invention not only has excellent photosensitivity, but also has high strength against thermal and mechanical shocks, and can be manufactured at low cost.

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

第１図〜第５図は本発明にかかわる電子写真感光体の厚
さ方向に拡大した断面図である。第６図は本発明の感光
体と比較用の感光体の残留表面電位と疲労時間の関係を
示すグラフであり、第７図は本発明の感光体と比較用の
感光体の表面電位と疲労時間の関係を示すグラフである
。 ■・・・導電性支持体　　２．２／　、　ｒ２１′、２
１１１．２１１１４・・・感光層３・・電荷発生物質　
　４・・・電荷搬送媒体又は電荷搬送層５・・電荷発生
層　　　６・・・保護層特許出願人　株式会社　リ　　
コ　　−手続補正帯（自発） １．事件の表示 昭和６３年特許願第２４７０３３号 ２、発明の名称 電子写真用感光体 ３、補正をする者 事件との関係　　特許出願人 住　所　　東京都大田区中馬込１丁１＝１３番６号名　
称　　（６７４）　　株式会社　リ　コ　−代表者　浜
　１）　　広 ４、代理人〒１５１ ５、補正命令の日付　　　自　発 ８、補正の内容 本願明細書中において以下のとおり補正を行います。 （１）第８頁第１行の 「 に訂正します。 （２）第１２頁第９行の 」を、 」 に訂正します。 （３）第３４頁の表−３を以下のように訂正します。 「　　　　　　　表−３ 」 （４）第３５頁第５行の「電子発生物質」を、「電荷発
生物質」に訂正します。 （５）第６図及び第７図を別紙のとおり訂正します。1 to 5 are cross-sectional views enlarged in the thickness direction of an electrophotographic photoreceptor according to the present invention. FIG. 6 is a graph showing the relationship between the residual surface potential and fatigue time of the photoreceptor of the present invention and a comparison photoreceptor, and FIG. 7 is a graph showing the relationship between the surface potential and fatigue time of the photoreceptor of the invention and the comparison photoreceptor. It is a graph showing a time relationship. ■...Conductive support 2.2/, r21', 2
111.21114...Photosensitive layer 3...Charge generating substance
4...Charge transport medium or charge transport layer 5...Charge generation layer 6...Protective layer Patent applicant Ri Co., Ltd.
Co-procedural amendment band (voluntary) 1. Description of the case Patent Application No. 247033 of 1988 2, Title of the invention Electrophotographic photoreceptor 3, Person making the amendment Relationship to the case Patent applicant address 1-1-13-6 Nakamagome, Ota-ku, Tokyo given name
Name (674) Rico Co., Ltd. - Representative Hama 1) Hiro 4, Agent 〒151 5, Date of amendment order Voluntary 8, Contents of amendment The following amendments will be made in the specification of this application. (1) The first line of page 8 is corrected to ``.'' (2) The 9th line of page 12 is corrected to ``. (3) Table 3 on page 34 is corrected as follows. “Table 3” (4) “Electron generating substance” in line 5 of page 35 will be corrected to “charge generating substance”. (5) Figures 6 and 7 will be corrected as shown in the attached sheet.

Claims (1)

【特許請求の範囲】[Claims] （１）導電性支持体上に下記一般式（ I ）で表わされ
るアミノビフェニル化合物の少くとも１種を有効成分と
して含有する感光層を有することを特徴とする電子写真
用感光体。▲数式、化学式、表等があります▼（ I ） （式中、Ｒ＾１、Ｒ＾３及びＲ＾４は水素原子、アミノ
基、アルコキシ基、チオアルコキシ基、アリールオキシ
基、メチレンジオキシ基、置換もしくは無置換のアルキ
ル基、ハロゲン原子又は置換もしくは無置換のアリール
基を、Ｒ＾２は水素原子、アルコキシ基、置換もしくは
無置換のアルキル基又はハロゲンを表わす。但し、Ｒ＾
１、Ｒ＾２、Ｒ＾３およびＲ＾４がすべて水素原子であ
る場合は除く。またｋ、ｌ、ｍ及びｎは１、２、３又は
４の整数であり、各々が２、３又は４の整数の時は前記
Ｒ＾１、Ｒ＾２、Ｒ＾３及びＲ＾４は同一でも異なって
いてもよい。）(1) An electrophotographic photoreceptor comprising, on a conductive support, a photosensitive layer containing as an active ingredient at least one aminobiphenyl compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R^1, R^3 and R^4 are hydrogen atoms, amino groups, alkoxy groups, thioalkoxy groups, aryloxy groups, methylenedioxy groups , a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted aryl group, and R^2 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group, or a halogen.However, R^
1. Except when R^2, R^3 and R^4 are all hydrogen atoms. In addition, k, l, m, and n are integers of 1, 2, 3, or 4, and when each is an integer of 2, 3, or 4, the above R^1, R^2, R^3, and R^4 are They may be the same or different. )
JP63247033A 1987-10-20 1988-09-30 Electrophotographic photoreceptor Expired - Lifetime JP2753582B2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP26566287 1987-10-20
JP63-10330 1988-01-19
JP62-265662 1988-01-19
JP1033088 1988-01-19

Publications (2)

Publication Number Publication Date
JPH01280763A true JPH01280763A (en) 1989-11-10
JP2753582B2 JP2753582B2 (en) 1998-05-20

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ID=26345591

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02134642A (en) * 1988-11-15 1990-05-23 Canon Inc Electrophotographic sensitive body
JPH02134643A (en) * 1988-11-15 1990-05-23 Canon Inc Electrophotographic sensitive body
JPH02178668A (en) * 1988-12-29 1990-07-11 Canon Inc Electrophotographic sensitive body
JPH02190862A (en) * 1989-01-20 1990-07-26 Canon Inc Electrophotographic sensitive body
JPH03211559A (en) * 1990-01-17 1991-09-17 Canon Inc Electrophotographic sensitive body
US5495049A (en) * 1993-03-22 1996-02-27 Fuji Xerox Co., Ltd. Triarylamine compounds useful in electrophotographic photoreceptors
US5856596A (en) * 1994-02-23 1999-01-05 Fuji Xerox Co., Ltd. Process for preparing mono-iodinated aromatic compound
JPH11184108A (en) * 1997-12-25 1999-07-09 Canon Inc Electrophotographic photoreceptor, process cartridge and electrophotographic apparatus
US7138555B2 (en) 2004-04-20 2006-11-21 Xerox Corporation Process for preparing iodoaromatic compounds and using the same
JP2013254135A (en) * 2012-06-08 2013-12-19 Konica Minolta Inc Electrophotographic photoreceptor, electrophotographic image forming method, and electrophotographic image forming apparatus
JP2013257504A (en) * 2012-06-14 2013-12-26 Konica Minolta Inc Organic photoreceptor, manufacturing method thereof, and image forming apparatus

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6323162A (en) * 1986-02-28 1988-01-30 Mita Ind Co Ltd Electrophotographic sensitive body

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6323162A (en) * 1986-02-28 1988-01-30 Mita Ind Co Ltd Electrophotographic sensitive body

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02134642A (en) * 1988-11-15 1990-05-23 Canon Inc Electrophotographic sensitive body
JPH02134643A (en) * 1988-11-15 1990-05-23 Canon Inc Electrophotographic sensitive body
JPH02178668A (en) * 1988-12-29 1990-07-11 Canon Inc Electrophotographic sensitive body
JPH0516019B2 (en) * 1988-12-29 1993-03-03 Canon Kk
JPH02190862A (en) * 1989-01-20 1990-07-26 Canon Inc Electrophotographic sensitive body
JPH03211559A (en) * 1990-01-17 1991-09-17 Canon Inc Electrophotographic sensitive body
US5495049A (en) * 1993-03-22 1996-02-27 Fuji Xerox Co., Ltd. Triarylamine compounds useful in electrophotographic photoreceptors
US5587263A (en) * 1993-03-22 1996-12-24 Fuji Xerox Co., Ltd. Electrophotographic photoreceptor using triarylamine compounds
US5856596A (en) * 1994-02-23 1999-01-05 Fuji Xerox Co., Ltd. Process for preparing mono-iodinated aromatic compound
JPH11184108A (en) * 1997-12-25 1999-07-09 Canon Inc Electrophotographic photoreceptor, process cartridge and electrophotographic apparatus
US7138555B2 (en) 2004-04-20 2006-11-21 Xerox Corporation Process for preparing iodoaromatic compounds and using the same
JP2013254135A (en) * 2012-06-08 2013-12-19 Konica Minolta Inc Electrophotographic photoreceptor, electrophotographic image forming method, and electrophotographic image forming apparatus
JP2013257504A (en) * 2012-06-14 2013-12-26 Konica Minolta Inc Organic photoreceptor, manufacturing method thereof, and image forming apparatus

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