JPS6219743B2 - - Google Patents

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Publication number
JPS6219743B2
JPS6219743B2 JP17045679A JP17045679A JPS6219743B2 JP S6219743 B2 JPS6219743 B2 JP S6219743B2 JP 17045679 A JP17045679 A JP 17045679A JP 17045679 A JP17045679 A JP 17045679A JP S6219743 B2 JPS6219743 B2 JP S6219743B2
Authority
JP
Japan
Prior art keywords
photoreceptor
weight
disazo pigment
charge
group
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
JP17045679A
Other languages
Japanese (ja)
Other versions
JPS5694358A (en
Inventor
Mitsuru Hashimoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ricoh Co Ltd
Original Assignee
Ricoh Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ricoh Co Ltd filed Critical Ricoh Co Ltd
Priority to JP17045679A priority Critical patent/JPS5694358A/en
Publication of JPS5694358A publication Critical patent/JPS5694358A/en
Publication of JPS6219743B2 publication Critical patent/JPS6219743B2/ja
Granted legal-status Critical Current

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  • Photoreceptors In Electrophotography (AREA)

Description

【発明の詳现な説明】[Detailed description of the invention]

本発明は電子写真甚の感光䜓に関し、曎に詳し
くは有効成分ずしおゞスアゟ顔料を含有する感光
局を有する新芏な感光䜓に関する。 埓来、導電性支持䜓䞊にアゟ顔料を有効成分ず
しお含有する感光局を蚭けた電子写真甚感光䜓ず
しおは䟋えばモノアゟ顔料を甚いたもの特公昭
44―16474号公報やベンゞン系のゞスアゟ顔料
を甚いたもの特開昭47―37543号公報等が公
知である。これらのアゟ顔料は前述のように感光
局の有効成分ずしお確かに有甚な材料ではある
が、電子写真プロセスの点から感光䜓に察する
皮々の芁求を考慮するず、末だこれらの芁求を充
分に満足するものが埗られおいないのが実情であ
る。埓぀おアゟ顔料に限らず、有効成分ずしお働
く顔料を広範囲に遞択し埗るように倚皮類にする
こずは曎に重芁なこずであり、それによ぀お初め
おある皮のプロセスに適切な感光䜓を提䟛するこ
ずが可胜ずなる。即ち、電子写真プロセスにおい
おは感光䜓の有効成分ずしお働き埗る顔料の皮類
はできるだけ倚いこずが望たしい。 本発明の第䞀の目的は各皮の電子写真プロセス
に有効成分ずしお働き埗る新芏なゞスアゟ顔料を
含む電子写真甚感光䜓を提䟛するこずである。 本発明の第二の目的は有効成分ずしお働き埗る
ゞスアゟ顔料を広範に遞択し埗る電子写真甚感光
䜓を提䟛するこずである。 本発明の第䞉の目的は前述のようなゞスアゟ顔
料を含む新たな高感床、高可撓性の電子写真感光
䜓を提䟛するこずである。 本発明者らは䞀矀のゞスアゟ顔料を補造し、そ
れらの感光䜓ぞの応甚を怜蚎した結果、䞋蚘䞀般
匏で衚わされるゞスチリルベンれン骚栌を有する
ゞスアゟ顔料が感光䜓のすぐれた有効成分ずしお
働き埗るこずを知芋し、本発明を完成したもので
ある。 即ち本発明は導電性支持䜓䞊に、䞋蚘䞀般匏 䜆し匏䞭Arは眮換又は非眮換のプニル
基、眮換又は非眮換のナフチル基、アントリル
基、ピレニル基、ピリゞル基、チ゚ニル基、フリ
ル基及びカルバゟリル基を衚わす で瀺されるゞスアゟ顔料を有効成分ずしお含有す
る感光局を有するこずを特城ずする電子写真甚感
光䜓を提䟛するものである。 以䞋に本発明で䜿甚される前蚘䞀般匏の化合物
の具䜓䟋を構造匏で瀺す。
The present invention relates to a photoreceptor for electrophotography, and more particularly to a novel photoreceptor having a photosensitive layer containing a disazo pigment as an active ingredient. Conventionally, as an electrophotographic photoreceptor in which a photosensitive layer containing an azo pigment as an active ingredient is provided on a conductive support, for example, a photoreceptor using a monoazo pigment (Tokuko Showa)
44-16474) and one using a benzine-based disazo pigment (Japanese Patent Application Laid-open No. 47-37543) are known. As mentioned above, these azo pigments are certainly useful materials as active ingredients in the photosensitive layer, but considering the various requirements for photoreceptors from the viewpoint of electrophotographic processes, it is difficult to fully satisfy these requirements. The reality is that we are not getting anything. Therefore, it is even more important to have a wide variety of pigments, not just azo pigments, that can serve as active ingredients, and only then can a photoreceptor suitable for a certain process be provided. becomes possible. That is, in the electrophotographic process, it is desirable to have as many types of pigments as possible that can act as active ingredients in the photoreceptor. A first object of the present invention is to provide an electrophotographic photoreceptor containing a novel disazo pigment that can serve as an active ingredient in various electrophotographic processes. A second object of the present invention is to provide an electrophotographic photoreceptor that allows a wide selection of disazo pigments that can serve as active ingredients. A third object of the present invention is to provide a new highly sensitive and highly flexible electrophotographic photoreceptor containing the above-mentioned disazo pigment. The present inventors produced a group of disazo pigments and studied their application to photoreceptors. As a result, the disazo pigments having a distyrylbenzene skeleton represented by the following general formula can serve as an excellent active ingredient for photoreceptors. Based on this knowledge, the present invention was completed. That is, the present invention provides the following general formula on a conductive support: (However, in the formula, Ar represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, anthryl group, pyrenyl group, pyridyl group, thienyl group, furyl group, or carbazolyl group). An object of the present invention is to provide an electrophotographic photoreceptor characterized by having a photosensitive layer containing: Specific examples of the compounds of the above general formula used in the present invention are shown below in terms of structural formulas.

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【衚】【table】

【衚】 これらの、ゞスアゟ顔料は特開昭54―7428号公
報に蚘茉の―ゞスチリルベンれン―4′
4″―ビスゞアゟニりムビステトラフルオロボレヌ
トず、各顔料に察応するカツプラヌずを適圓な有
機溶媒、䟋えば―ゞメチルホルムアミド
DMF䞭で、アルカリの存圚䞋カツプリングす
るこずにより容易に補造するこずが出来る。たた
ここで䜿甚されるカツプラヌはFranzenらの方法
J.Prak.Chem.〔〕78164に埓い―ヒドロ
キシ――ナフト゚酞ヒドラゞドずアルデヒドを
䟋えばアルコヌルなどの有機溶媒䞭で加熱するこ
ずにより容易に補造されるものである。 以䞋にその補造の具䜓䟋を瀺す。 補造䟋 ―ゞスチリルベンれン―4′4″―ビスゞ
アゟニりムビステトラフルオロボレヌト2.55
―シドロキシ――ナフト゚酞ベンザルヒドラゞ
ド2.90をDMF300mlに溶解し、これに酢酞ナト
リりム1.64及び氎14mlよりなる溶液を宀枩にお
滎䞋した。滎䞋終了埌同枩床にお時間撹拌し、
折出した結晶を取した。残枣に300mlのDMFを
加えお80℃で時間撹拌したのち、再び結晶を
取し、この操䜜を曎に回くり返した。氎掗埌也
燥しお化合物No.のゞスアゟ顔料3.77を青黒色
結晶ずしお埗た。 元玠分析倀 蚈算倀 実枬倀  76.13 75.95  4.63 4.53  12.25 12.19 赀倖線吞収スペクトルKBrdiskを第図に瀺
す。 cp第アミド 1670cm-1 本発明の感光䜓は以䞊のようなゞスアゟ顔料を
含むものであるが、これら顔料の応甚の仕方によ
り第〜図の圢態をずるこずができる。第図
の感光䜓は導電性支持䜓䞊にゞスアゟ顔料
ここでは光導電性物質ずしお䜿甚される〜暹
脂結着剀系感光局を蚭けたものである。第
図の感光䜓は導電性支持䜓䞊にゞスアゟ顔料
ここでは電荷担䜓発生物質ずしお䜿甚される
〜電荷移動媒䜓電荷移動性物質及び暹脂結着剀
の混合物系感光局′を蚭けたものである。
たた第〜図の感光䜓は第図の感光䜓の倉圢
で、感光局″はゞスアゟ顔料を䞻䜓ず
する電荷担䜓発生局ず電荷移動媒䜓の局ずか
らな぀おいる。 これらの感光䜓における各組成分は、各々次の
ような珟象により感光䜓に察する効果をもたらし
めおいるものず考えられる。 第図の感光䜓においおゞスアゟ顔料は光導電
性物質ずしお䜜甚し、光枛衰に必芁な電荷担䜓の
生成及び移動は顔料粒子を介しお行なわれる。第
図の感光䜓の堎合は電荷移動性物質は結着剀
及び堎合により可塑剀ず共に電荷移動媒䜓を
圢成し、䞀方ゞスアゟ顔料は電荷担䜓発生物質ず
しお䜜甚する。この電荷移動媒䜓はゞスアゟ顔料
のような電荷担䜓の生成胜力はないが、ゞスアゟ
顔料から発生した電荷担䜓を受け入れ、これを移
動する胜力を持぀おいる。即ち第図の感光䜓で
は光枛衰に必芁な電荷担䜓の生成はゞスアゟ顔料
によ぀お行なわれ、䞀方、電荷担䜓の移動は䞻に
電荷移動媒䜓により行なわれる。ここで電荷移動
媒䜓に曎に芁求される基本的条件は電荷移動媒䜓
の吞収波長領域がゞスアゟ顔料の䞻に可芖郚の吞
収波長領域ず重ならないこずである。これはゞス
アゟ顔料に効率良く電荷担䜓を発生させるために
顔料衚面たで光を透過させる必芁があるからであ
る。しかし䟋えばある特定波長だけに感床を有す
る感光䜓の堎合はこの限りではない。埓぀お電荷
移動媒䜓及びゞスアゟ顔料の䞡者の吞収波長は完
党に重耇しなければよい。次に第図の感光䜓で
は電荷移動媒䜓局を透過しお来た光が電荷担䜓発
生局である感光局″に到達し、その郚分のゞス
アゟ顔料で電荷担䜓の生成が起こり、䞀方、電荷
移動媒䜓局は電荷担䜓の泚入を受け、その移動を
行なうもので、光枛衰に必芁な電荷担䜓の生成は
ゞスアゟ顔料で、たた電荷担䜓の移動は電荷移動
媒䜓でずいうメカニズムは第図に瀺した感光䜓
の堎合ず同様である。ここでもゞスアゟ顔料は電
荷担䜓発生物質である。なお、第図の感光䜓に
おける電荷移動局及び電荷担䜓発生局の䜜甚機構
も第図の感光䜓の堎合ず同じである。 第図の感光䜓を䜜成するにはゞスアゟ顔料の
埮粒子を結着剀溶液䞭に分散した分散液を導電性
支持䜓䞊に塗垃也燥すればよい。第図の感光䜓
を䜜成するにはゞスアゟ顔料の埮粒子を電荷移動
性物質及び結着剀を溶解した溶液䞭にゞスアゟ顔
料の埮粒子を分散せしめ、これを導電性支持䜓䞊
に塗垃也燥すればよい。たた第図の感光䜓は導
電性支持䜓䞊にゞスアゟ顔料を真空蒞着するか、
或いはゞスアゟ顔料の埮粒子を必芁あれば結着剀
を溶解した適圓な溶媒䞭に溶解し、これを導電性
支持䜓䞊に塗垃也燥し、曎に必芁あれば䟋えばバ
フ研摩等の方法により衚面仕䞊げするか膜厚を調
敎した埌、その䞊に電荷移動性物質及び結着剀を
含む溶液を塗垃也燥しお埗られる。なお第図の
感光䜓の堎合は第図の感光䜓の䜜成法においお
膜圢成順序を逆にすればよい。いずれにしおも本
発明で䜿甚されるゞスアゟ顔料はボヌルミル等に
より粒埄Ό以䞋、奜たしくはΌ以䞋に粉砕し
お甚いられる。塗垃法は通垞の手段、䟋えばドク
タヌブレヌド、ワむダヌバヌなどで行なう。感光
局の厚さは第図及び第図のものでは玄〜50
Ό、奜たしくは〜20Όである。たた第〜図
のものでは電荷担䜓発生局の厚みは、Ό以䞋、
奜たしくはΌ以䞋がよく、電荷移動媒䜓局の厚
さは玄〜50Ό、奜たしくは〜20Όである。た
た第図の感光䜓においお感光局䞭のゞスアゟ顔
料の割合は感光局に察し30〜70重量奜たしくは
箄50重量が適圓である。前述のように第図
の感光䜓の堎合は、ゞスアゟ顔料は光導電物質ず
しお䜜甚し、光枛衰に必芁な電荷担䜓の生成及び
移動は顔料粒子を介しお行なわれるので、顔料粒
子間の接觊は感光局衚面から支持䜓たで連続しお
いるこずが望たしい。このため感光局に占める顔
料の割合は比范的倚い方が望たしいが、感光局の
匷床及び感床を考慮するず、玄50重量がよ
い。 第図の感光䜓においお、感光局䞭のゞスアゟ
顔料の占める割合は50重量以䞋、奜たしくは20
重量以䞋であり、たた電荷移動性物質の割合は
10〜95重量、奜たしくは30〜90重量である。
たた第〜図の感光䜓における電荷移動媒䜓局
䞭の電荷移動性物質の割合は第図の感光䜓の感
光局の堎合ず同様、10〜95重量、奜たしくは30
〜90重量である。なお第〜図のいずれの感
光䜓の䜜成においおも結着剀ず共に可塑剀を䜵甚
するこずができる。 本発明の感光䜓においお導電性支持䜓ずしおは
アルミニりム等の金属板又は金属箔、アルミニり
ムなどの金属を蒞着したプラスチツクフむルム、
或いは導電凊理を斜した玙等が䜿甚される。結着
剀ずしおはポリアミド、ポリりレタン、ポリ゚ス
テル、゚ポキシ暹脂、ポリケトン、ポリカヌボネ
ヌトなどの瞮合暹脂やポリビニルケトン、ポリス
チレン、ポリ――ビニルカルバゟヌル、ポリア
クリルアミドなどのビニル重合䜓などが挙げられ
るが、絶瞁性で䞔぀接着性のある暹脂は党お䜿甚
できる。可塑剀ずしおはハロゲン化パラフむン、
ポリ塩化ビプニル、ゞメチルナフタレン、ゞプ
チルフタレヌトなどが挙げられる。たた電荷移動
性物質ずしおは高分子のものではポリ――ビニ
ルカルバゟヌル、ハロゲン化ポリ――ビニルカ
ルバゟヌル、ポリビニルピレン、ポリビニルむン
ドロキノキサリン、ポリビニルゞベンゟチオプ
ン、ポリビニルアントラセン、ポリビニルアクリ
ゞンなどのビニル重合䜓やピレン〜ホルムアルデ
ヒド暹脂、プロムピレン〜ホルムアルデヒド暹
脂、゚チルカルバゟヌル〜ホルムアルデヒド暹
脂、クロロ゚チルアルバゟヌル〜ホルムアルデヒ
ド暹脂などの瞮合暹脂が、たた䜎分子単量䜓
のものではフルオレノン、―ニトロ――フル
オレノン、―ゞニトロ――フルオレノ
ン、―トリニトロ――フルオレノ
ン、―テトラニトロ――フルオ
レノン、4H―むンデノ〔―〕チオフ
゚ン――オン、―ニトロ―4H―むンデノ
〔―〕チオプン――オン、
―トリニトロ―4H―むンデノ〔―〕
チオプン――オン、8H―むンデノ〔
―〕チオプン――オン、―ニトロ―8H
―むンデノ〔―〕チオプン――オ
ン、―ブロム――ゞニトロ―4H―むン
デノ〔―〕チオプン、―ゞニト
ロ―4H―むンデノ〔―〕チオプン、
―ニトロゞベンゟチオプン、―ゞニト
ロベンゟチオプン、―ニトロゞベンゟチオフ
゚ン――オキサむド、―ゞニトロゞベン
ゟチオプン――オキサむド、―ト
リニトロ―ゞベンゟチオプン――ゞオキ
サむド、―ニトロ―ゞベンゟチオプン―
―ゞオキサむド、―ゞニトロ―ゞベンゟ
チオプン――ゞオキサむド、―ゞシア
ノメチレン―4H―むンデノ〔―〕チオ
プン、―ゞニトロ――ゞシアノメチレ
ン―4H―むンデノ〔―〕チオプン、
―テトラニトロベンゟ〔〕シン
ノリン――オキサむド、10―トリニト
ロベンゟ〔〕シンノリン――オキサむド、
―トリニトロベンゟ〔〕シンノリン
――オキサむド、―トリニトロチオ
キサントン、―トリニトロ―10―
プナンスレンキノン、―ナフトキノンベ
ンゟ〔〕アンスラセン―12―ゞオン、
―トリニトロ――ゞシアノメチレンフル
オレン、テトラクロル無氎フタル酞、―ブロム
ピレン、―メチルピレン、―゚チルピレン、
―アセチルピレン、カルバゟヌル、―゚チル
カルバゟヌル、―β―クロロ゚チルカルバゟヌ
ル、―β―ヒドロキシ゚チルカルバゟヌル、
―プニルむンドヌル、―プニルナフタレ
ン、―ビス―ゞ゚チルアミノプニ
ル――オキサゞアゟヌル、―
ビス―ゞ゚チルアミノプニル
―トリアゟヌル、―プニル―――ゞ゚
チルアミノスチリル―――ゞ゚チルアミ
ノプニルピラゟリン、―プニル――
ゞ゚チルアミノプニル――プニルオキ
サゟヌル、トリプニルアミン、トリス―ゞ
゚チルアミノプニルメタン、―ビス
ゞベンゞルアミノ――゚チルカルバゟヌル
――゚チルカルバゟヌル――アルデヒド―
―メチル―トプニルヒドラゟンなどが挙げられ
る。これらの電荷移動性物質は単独又は皮以䞊
混合しお甚いられる。 なお以䞊のようにしお埗られる感光䜓にはいず
れも導電性支持䜓ず感光局の間に必芁に応じお接
着局又はバリダ局を蚭けるこずができる。これら
の局に甚いられる材料ずしおはポリアミド、ニト
ロセルロヌス、酞化アルミニりムなどが適圓で、
たた膜厚はΌ以䞋が奜たしい。 本発明の感光䜓を甚いお耇写を行なうには、感
光局面に垯電、露光を斜した埌、珟像を行ない、
必芁によ぀お玙などぞ転写を行うこずにより達成
される。 本発明の感光䜓は䞀般に感床が高く、たた可撓
性に富むなどのすぐれた利点を有する。 以䞋に実斜䟋を瀺す。 実斜䟋  ポリ゚ステル暹脂デナポン瀟補、ポリ゚ステ
ルアドヒシヌブ49000重量郚、No.のゞスア
ゟ顔料重量郚及びテトラヒドロフラン26重量郹
をボヌルミル䞭で粉砕混合し、埗られた分散液
を、アルミニりム蒞着したポリ゚ステルフむルム
䞊にドクタヌブレヌドを甚いお塗垃し100℃で10
分間也燥しお厚さΌの感光局を持぀た第図の
圢態の感光䜓を埗た。 次にこの感光䜓の感光局面に垂販の静電耇写玙
詊隓装眮により6KVのコロナ攟電を20秒行぀お
正垯電させた埌、20秒間暗所に攟眮し、その時の
衚面電䜍ppボルトを枬定し、぀いでタング
ステンランプから、その衚面が照床20ルツクスに
なるよう感光局に光照射を斜し、その衚面電䜍が
ppの1/2になる迄の時間秒を求めお露光量
1/2ルツクス・秒ずした。その結果はpp
730V、1/2ルツクス・秒であ぀た。 実斜䟋 〜10 実斜䟋においおNo.のゞスアゟ顔料の代りに
䞋蚘衚―に瀺す番号のゞスアゟ顔料を倫々甚い
た他は実斜䟋ず同じ感光䜓䜜成法に埓぀お感光
䜓を䜜成し、以䞋これらの感光䜓に぀いお実斜䟋
ず同じ枬定を行ない衚―の結果を埗た。
[Table] These disazo pigments are 1,4-distyrylbenzene-4',
Easily produced by coupling 4″-bisdiazonium bistetrafluoroborate and a coupler corresponding to each pigment in an appropriate organic solvent, such as N,N-dimethylformamide (DMF), in the presence of an alkali. The coupler used here is prepared by heating 2-hydroxy-3-naphthoic acid hydrazide and aldehyde in an organic solvent such as alcohol according to the method of Franzen et al. (J. Prak. Chem. [2] 78 , 164). A specific example of its production is shown below. Production example 1,4-distyrylbenzene-4',4''-bisdiazonium bistetrafluoroborate 2.55g2
2.90 g of -cidroxy-3-naphthoic acid benzalhydrazide was dissolved in 300 ml of DMF, and a solution consisting of 1.64 g of sodium acetate and 14 ml of water was added dropwise thereto at room temperature. After completing the dropwise addition, stir at the same temperature for 2 hours.
The precipitated crystals were collected. After adding 300 ml of DMF to the residue and stirring at 80°C for 2 hours, crystals were collected again and this operation was repeated two more times. After washing with water and drying, 3.77 g of disazo pigment Compound No. 1 was obtained as blue-black crystals. Elemental analysis value Calculated value Actual value C% 76.13 75.95 H% 4.63 4.53 N% 12.25 12.19 The infrared absorption spectrum (KBrdisk) is shown in Figure 5. V cp (secondary amide) 1670 cm -1 The photoreceptor of the present invention contains the above-mentioned disazo pigments, and can take the forms shown in Figures 1 to 4 depending on how these pigments are applied. The photoreceptor in FIG. 1 has a disazo pigment 4 on a conductive support 1.
(Here, it is used as a photoconductive substance.) A photosensitive layer 2 containing three resin binders is provided. Second
The photoreceptor in the figure has a disazo pigment 4 on a conductive support 1.
(here used as charge carrier generating material)
-A charge transfer medium (a mixture of a charge transfer substance and a resin binder) 5-based photosensitive layer 2' is provided.
The photoreceptor shown in FIGS. 3 and 4 is a modification of the photoreceptor shown in FIG. It is thought that each component in these photoreceptors has an effect on the photoreceptor due to the following phenomenon. In the photoreceptor shown in Figure 1, the disazo pigment acts as a photoconductive substance. , the generation and transfer of the charge carriers necessary for photoattenuation takes place via the pigment particles. In the case of the photoreceptor of FIG. The disazo pigment, on the other hand, acts as a charge carrier generator.This charge transfer medium does not have the ability to generate charge carriers like the disazo pigment, but it has the ability to accept and transfer the charge carriers generated from the disazo pigment. That is, in the photoreceptor shown in Fig. 2, the generation of charge carriers necessary for light attenuation is carried out by the disazo pigment, while the movement of charge carriers is mainly carried out by the charge transfer medium. Another basic condition required for the medium is that the absorption wavelength region of the charge transfer medium does not overlap with the absorption wavelength region of the disazo pigment, which is mainly in the visible region.This is necessary in order to efficiently generate charge carriers in the disazo pigment. This is because it is necessary to transmit light to the pigment surface.However, this is not the case, for example, in the case of a photoreceptor that is sensitive only to a certain wavelength.Therefore, the absorption wavelength of both the charge transfer medium and the disazo pigment is completely Next, in the photoreceptor shown in Figure 3, the light that has passed through the charge transport medium layer reaches the photosensitive layer 2'', which is the charge carrier generation layer, and the disazo pigment in that area generates charge carriers. On the other hand, the charge transfer medium layer receives injection of charge carriers and transfers them. The generation of charge carriers necessary for light attenuation is performed by the disazo pigment, and the transfer of charge carriers is carried out by the charge transfer medium. The mechanism is similar to that of the photoreceptor shown in FIG. Here again, the disazo pigment is a charge carrier generating substance. The mechanism of action of the charge transfer layer and the charge carrier generation layer in the photoreceptor shown in FIG. 4 is also the same as that in the photoreceptor shown in FIG. 3. In order to produce the photoreceptor shown in FIG. 1, a dispersion of disazo pigment particles dispersed in a binder solution may be coated on a conductive support and dried. To create the photoreceptor shown in Figure 2, fine particles of disazo pigment are dispersed in a solution containing a charge transporting substance and a binder, and the particles are coated on a conductive support and dried. good. The photoreceptor shown in Fig. 3 is made by vacuum-depositing a disazo pigment on a conductive support, or
Alternatively, fine particles of a disazo pigment may be dissolved in a suitable solvent in which a binder is dissolved, if necessary, and this may be coated and dried on a conductive support, and if necessary, the surface may be finished by a method such as buffing. After adjusting the film thickness, a solution containing a charge transporting substance and a binder is applied thereon and dried. In the case of the photoreceptor shown in FIG. 4, the order of film formation may be reversed in the method for producing the photoreceptor shown in FIG. In any case, the disazo pigment used in the present invention is used after being ground to a particle size of 5 ÎŒm or less, preferably 2 ÎŒm or less using a ball mill or the like. Application is carried out by conventional means, such as a doctor blade or wire bar. The thickness of the photosensitive layer is approximately 3 to 50 mm for those in Figures 1 and 2.
Ό, preferably 5 to 20 Ό. In addition, in the case of FIGS. 3 and 4, the thickness of the charge carrier generation layer is 5Ό or less,
The thickness of the charge transport medium layer is preferably about 3 to 50 microns, preferably 5 to 20 microns. Further, in the photoreceptor shown in FIG. 1, the appropriate proportion of the disazo pigment in the photosensitive layer is 30 to 70% by weight, preferably about 50% by weight, based on the photosensitive layer. (As mentioned above, in the case of the photoreceptor shown in Figure 1, the disazo pigment acts as a photoconductive substance, and the generation and movement of charge carriers necessary for light attenuation occur through the pigment particles. It is desirable that the contact be continuous from the surface of the photosensitive layer to the support.For this reason, it is desirable that the proportion of the pigment in the photosensitive layer be relatively large, but considering the strength and sensitivity of the photosensitive layer, approximately 50% by weight should be good). In the photoreceptor shown in Figure 2, the proportion of the disazo pigment in the photosensitive layer is 50% by weight or less, preferably 20% by weight or less.
% by weight or less, and the proportion of charge-mobile substances is
10-95% by weight, preferably 30-90% by weight.
The proportion of the charge transporting substance in the charge transport medium layer of the photoreceptor shown in FIGS. 3 and 4 is 10 to 95% by weight, preferably 30
~90% by weight. In addition, a plasticizer can be used together with a binder in producing any of the photoreceptors shown in FIGS. 1 to 4. In the photoreceptor of the present invention, the conductive support may be a metal plate or metal foil such as aluminum, a plastic film on which metal such as aluminum is vapor-deposited,
Alternatively, paper or the like that has been subjected to conductive treatment may be used. Examples of binders include condensation resins such as polyamide, polyurethane, polyester, epoxy resin, polyketone, and polycarbonate, and vinyl polymers such as polyvinyl ketone, polystyrene, poly-N-vinylcarbazole, and polyacrylamide. In addition, any adhesive resin can be used. As a plasticizer, halogenated paraffin,
Examples include polychlorinated biphenyl, dimethylnaphthalene, and diptylphthalate. In addition, examples of charge-transferring substances include polymers such as poly-N-vinylcarbazole, halogenated poly-N-vinylcarbazole, polyvinylpyrene, polyvinylindoquinoxaline, polyvinyldibenzothiophene, polyvinylanthracene, and polyvinylacridine. Coalescence and condensation resins such as pyrene-formaldehyde resin, propylene-formaldehyde resin, ethylcarbazole-formaldehyde resin, chloroethyl albazole-formaldehyde resin, and low molecular weight (monomer)
Fluorenone, 2-nitro-9-fluorenone, 2,7-dinitro-9-fluorenone, 2,4,7-trinitro-9-fluorenone, 2,4,5,7-tetranitro-9-fluorenone, 4H -indeno[1,2,-b]thiophene-4-one, 2-nitro-4H-indeno[1,2-b]thiophene-4-one, 2,6,
8-trinitro-4H-indeno [1,2-b]
Thiophene-4-one, 8H-indeno [2,1
-b] Thiophene-8-one, 2-nitro-8H
-Indeno[2,1-b]thiophene-8-one, 2-bromo-6,8-dinitro-4H-indeno[1,2-b]thiophene, 6,8-dinitro-4H-indeno[1,2 -b] Thiofene,
2-nitrodibenzothiophene, 2,8-dinitrobenzothiophene, 3-nitrodibenzothiophene-5-oxide, 3,7-dinitrodibenzothiophene-5-oxide, 1,3,7-trinitro-dibenzothio Phen-5,5-dioxide, 3-nitro-dibenzothiophene-5,
5-dioxide, 3,7-dinitro-dibenzothiophene-5,5-dioxide, 4-dicyanomethylene-4H-indeno[1,2-b]thiophene, 6,8-dinitro-4-dicyanomethylene- 4H-indeno[1,2-b]thiophene,
1,3,7,9-tetranitrobenzo[c]cinnoline-5-oxide, 2,4,10-trinitrobenzo[c]cinnoline-6-oxide,
2,4,8-trinitrobenzo[c]cinnoline-6-oxide, 2,4,8-trinitrothioxanthone, 2,4,7-trinitro-9,10-
phenanthrenequinone, 1,4-naphthoquinonebenzo[a]anthracene-7,12-dione, 2,
4,7-trinitro-9-dicyanomethylenefluorene, tetrachlorophthalic anhydride, 1-bromopyrene, 1-methylpyrene, 1-ethylpyrene,
1-acetylpyrene, carbazole, N-ethylcarbazole, N-β-chloroethylcarbazole, N-β-hydroxyethylcarbazole, 2
-phenylindole, 2-phenylnaphthalene, 2,5-bis(4-diethylaminophenyl)-1,3,4-oxadiazole, 2,5-
Bis(4-diethylaminophenyl)1,3,4
-triazole, 1-phenyl-3-(4-diethylaminostyryl)-5-(4-diethylaminophenyl)pyrazoline, 2-phenyl-4-
(diethylaminophenyl)-5-phenyloxazole, triphenylamine, tris(4-diethylaminophenyl)methane, 3,6-bis(dibenzylamino)-9-ethylcarbazole-9-ethylcarbazole-3-aldehyde -1
-Methyl-tophenylhydrazone and the like. These charge transfer substances may be used alone or in combination of two or more. In any of the photoreceptors obtained as described above, an adhesive layer or a barrier layer may be provided between the conductive support and the photosensitive layer, if necessary. Suitable materials for these layers include polyamide, nitrocellulose, aluminum oxide, etc.
Further, the film thickness is preferably 1 ÎŒm or less. To perform copying using the photoreceptor of the present invention, the surface of the photosensitive layer is charged and exposed, and then developed.
This can be achieved by transferring the image to paper, etc., if necessary. The photoreceptor of the present invention generally has excellent advantages such as high sensitivity and flexibility. Examples are shown below. Example 1 1 part by weight of polyester resin (manufactured by DuPont, Polyester Adhesive 49000), 1 part by weight of No. 1 disazo pigment, and 26 parts by weight of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was mixed with aluminum. Apply it on the vapor-deposited polyester film using a doctor blade and heat it for 10 minutes at 100℃.
After drying for a minute, a photoreceptor having a photoreceptor layer having a thickness of 7 .mu.m as shown in FIG. 1 was obtained. Next, a +6KV corona discharge was applied to the photosensitive layer surface of the photoreceptor using a commercially available electrostatic copying paper tester for 20 seconds to positively charge it, and then it was left in a dark place for 20 seconds, and the surface potential at that time was V pp (volts). Then, the photosensitive layer is irradiated with light from a tungsten lamp so that the surface has an illuminance of 20 lux, and the time (seconds) until the surface potential becomes 1/2 of V pp is calculated as the exposure amount E. It was set to 1/2 (lux seconds). The result is V pp
= 730V, E 1/2 = 5 lux seconds. Examples 2 to 10 Photoreceptors were prepared according to the same photoreceptor preparation method as in Example 1, except that disazo pigments with the numbers shown in Table 1 below were used instead of disazo pigment No. 1 in Example 1. However, the same measurements as in Example 1 were carried out on these photoreceptors, and the results shown in Table 1 were obtained.

【衚】 実斜䟋 11 ポリ゚ステル暹脂実斜䟋ず同じ10重量
郚、―トリニトロ――フルオレノン
10重量郚、No.のゞスアゟ顔料重量郚及びテト
ラヒドロフラン198重量郚をボヌルミル䞭で粉砕
混合し、埗られた分散液を、アルミニアりムを蒞
着したポリ゚ステルフむルム䞊にドクタヌブレヌ
ドを甚いお塗垃し、100℃で10分間也燥しお厚さ
10Όの感光局を持぀た第図の圢態の感光䜓を䜜
成した。次にこの感光䜓のpp及び1/2を前蚘
実斜䟋で6KVのコロナ攟電を行぀たかわりに−
6KVのコロナ攟電を行぀た以倖は党く同様に枬定
し、pp390ボルト、1/2ルツクス・秒
の結果を埗た。 実斜䟋 12〜20 実斜䟋11においおNo.のゞスアゟ顔料の代りに
䞋蚘衚―に瀺す番号のゞスアゟ顔料を倫々甚い
お第図の圢態の感光䜓を䜜成し、以䞋実斜䟋11
ず同じ方法でpp及び1/2を求め衚―の結果
を埗た。
[Table] Example 11 10 parts by weight of polyester resin (same as Example 1), 2,4,7-trinitro-9-fluorenone
10 parts by weight, 2 parts by weight of No. 1 disazo pigment, and 198 parts by weight of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was applied onto a polyester film coated with aluminum using a doctor blade. Dry for 10 minutes at ℃ to thick
A photoreceptor having a photosensitive layer having a thickness of 10Ό and having the configuration shown in FIG. 2 was prepared. Next, V pp and E 1/2 of this photoreceptor were changed to - instead of +6 KV corona discharge in the previous example.
Measurements were made in exactly the same manner except that a 6 KV corona discharge was performed, and results were obtained of V pp =390 volts and E 1/2 =8 lux·sec. Examples 12 to 20 In Example 11, the disazo pigments shown in the numbers shown in Table 2 below were used in place of the No. 1 disazo pigment to prepare a photoreceptor in the form shown in Figure 2.
V pp and E 1/2 were determined using the same method as above, and the results shown in Table 2 were obtained.

【衚】 実斜䟋 21 ポリ゚ステル暹脂実斜䟋ず同じ10重量
郚、―ビス―ゞ゚チルアミノプニ
ル―オキサゞアゟヌル10重量郚、No.
のゞスアゟ顔料重量郚及びテトラヒドロフラ
ン198重量郚をボヌルミル䞭で粉砕混合し、埗ら
れた分散液を、アルミニりムを蒞着したポリ゚ス
テルフむルム䞊にドクタヌブレヌドを甚いお塗垃
し、120℃で10分間也燥しお厚さ10Όの感光局を
持぀第図の圢態の感光䜓を䜜成した。以䞋この
感光䜓に぀いお実斜䟋ず同じ枬定を行ない、
pp900ボルト、1/2ルツクス・秒の結果
を埗た。 実斜䟋 22〜30 実斜䟋21においおNo.のゞスアゟ顔料の代りに
倫々䞋蚘衚―のゞスアゟ顔料を甚いた他は実斜
䟋21ず同じ方法で第図の圢態の感光䜓を䜜成
し、以䞋実斜䟋ず同じ枬定を行い衚―の結果
を埗た。
[Table] Example 21 10 parts by weight of polyester resin (same as Example 1), 10 parts by weight of 2,5-bis(4-diethylaminophenyl) 1,3,4-oxadiazole, No.
2 parts by weight of the disazo pigment of No. 1 and 198 parts by weight of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was applied onto a polyester film coated with aluminum using a doctor blade, and dried at 120°C for 10 minutes. A photoreceptor having a photosensitive layer having a thickness of 10 Όm as shown in FIG. 2 was prepared. Hereinafter, the same measurements as in Example 1 were performed on this photoreceptor, and the V
We obtained results of pp = 900 volts and E 1/2 = 8 lux·sec. Examples 22 to 30 A photoreceptor having the form shown in FIG. 2 was prepared in the same manner as in Example 21, except that the disazo pigments shown in Table 3 below were used in place of the No. 1 disazo pigment in Example 21. The same measurements as in Example 1 were carried out, and the results shown in Table 3 were obtained.

【衚】 実斜䟋 31 ポリ――ビニルカルバゟヌル200重量郚、
―トリニトロ――フルオレノン33重
量郚、ポリ゚ステル暹脂実斜䟋ず同じ20重
量郚及びNo.のゞスアゟ顔料20重量郚をテトラヒ
ドロフラン1780重量郚に加え、ボヌルミル䞭で粉
砕混合し、埗られた分散液を、アルミニりムを蒞
着したポリ゚ステルフむルム䞊にドクタヌブレヌ
ドで塗垃し、100℃で10分間、぀いで120℃で分
間也燥し、厚さ13Όの感光局を有する第図の圢
態の感光䜓を䜜成し、実斜䟋ず同じ枬定を行な
぀たずころ、pp1200ボルト、1/2ルツ
クス・秒の結果を埗た。 実斜䟋 32〜40 実斜䟋31においおNo.のゞスアゟ顔料の代りに
倫々䞋蚘衚―のゞスアゟ顔料を甚いお第図の
圢態の感光䜓を䜜成し、実斜䟋ず同じ方法で
pp及び1/2を求め衚―の結果を埗た。
[Table] Example 31 200 parts by weight of poly-N-vinylcarbazole,
33 parts by weight of 2,4,7-trinitro-9-fluorenone, 20 parts by weight of polyester resin (same as in Example 1), and 20 parts by weight of No. 1 disazo pigment were added to 1780 parts by weight of tetrahydrofuran, and the mixture was ground and mixed in a ball mill. The resulting dispersion was applied with a doctor blade onto a polyester film on which aluminum had been vapor-deposited, and dried at 100°C for 10 minutes and then at 120°C for 5 minutes to form a photosensitive layer with a thickness of 13Ό as shown in Figure 2. When a photoreceptor of the same type was prepared and the same measurements as in Example 1 were carried out, the results were that V pp =1200 volts and E 1/2 =3 lux·sec. Examples 32 to 40 In Example 31, a photoreceptor having the form shown in FIG.
The pp and E 1/2 were calculated and the results shown in Table 4 were obtained.

【衚】【table】

【衚】 実斜䟋 41 No.のゞスアゟ顔料重量郚及びテトラヒドロ
フラン98重量郚をボヌルミル䞭で粉砕混合し、埗
られた分散液を、アルミニりム蒞着ポリ゚ステル
フむルム䞊にドクタヌブレヌドで塗垃し、自然也
燥しお厚さΌの電荷担䜓発生局を圢成せしめ
た。䞀方、―トリニトロ――フルオ
レノン重量郚、ポリカヌボネヌト〔(æ ª)テむゞン
補、パンラむト〕重量郚及びテトラヒドロフ
ラン46重量郚を混合しお分散液ずし、これを前蚘
電荷担䜓発生局䞊にドクタヌブレヌドで塗垃し、
100℃で10分間也燥しお厚さ10Όの電荷移動媒䜓
局を圢成せしめ、第図の圢態の感光䜓を埗た。
䞊蚘のようにしお埗た感光䜓に぀いお、実斜䟋
ず同時に枬定し、ppは680ボルト、1/2は10
ルツクス・秒の結果を埗た。 実斜䟋 42〜50 実斜䟋41においおNo.のゞスアゟ顔料の代りに
䞋蚘衚―のゞスアゟ顔料を倫々甚いた他は同じ
方法で第図の圢態の感光䜓を䜜成した。これら
感光䜓のpp及び1/2を衚―に瀺す。
[Table] Example 41 2 parts by weight of No. 1 disazo pigment and 98 parts by weight of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was applied onto an aluminum-deposited polyester film with a doctor blade and air-dried. A charge carrier generation layer having a thickness of 1 ÎŒm was formed. On the other hand, 2 parts by weight of 2,4,7-trinitro-9-fluorenone, 2 parts by weight of polycarbonate [Panlite L, manufactured by Teijin Co., Ltd.], and 46 parts by weight of tetrahydrofuran were mixed to prepare a dispersion liquid, and this was used as the charge carrier. Apply it on the generation layer with a doctor blade,
A charge transfer medium layer having a thickness of 10 Όm was formed by drying at 100° C. for 10 minutes, and a photoreceptor having the form shown in FIG. 3 was obtained.
Example 1 Regarding the photoreceptor obtained as described above
Measured at the same time, V pp is 680 volts, E 1/2 is 10
I got the result of lux sec. Examples 42 to 50 Photoreceptors having the form shown in FIG. 3 were prepared in the same manner as in Example 41 except that the disazo pigments shown in Table 5 below were used in place of the disazo pigment No. 1. Table 5 shows the V pp and E 1/2 of these photoreceptors.

【衚】【table】

【衚】 実斜䟋 51 No.のゞスアゟ顔料重量郚及びテトラヒドロ
フラン98重量郚をボヌルミル䞭で粉砕混合し、埗
られた分散液をアルミニりム蒞着ポリ゚ステルフ
むルム䞊にドクタヌブレヌドで塗垃し自然也燥し
お厚さΌの電荷担䜓発生局を圢成した。䞀方、
――ゞ゚チルアミノスチリルアントラセ
ン重量郚、ポリカヌボネヌト実斜䟋41に同
じ重量郚及びテトラヒドロフラン46重量郚を
混合しお溶解し、これを前蚘電荷担䜓発生局䞊に
ドクタヌブレヌドで塗垃し、120℃で10分間也燥
しお厚さ10Όの電荷移動媒䜓局を圢成せしめ、第
図の積局型感光䜓を埗た。䞊蚘のようにしお埗
た感光䜓に぀いお−6KVのコロナ攟電を行な぀た
以倖は実斜䟋ず同様に枬定を行い、このものの
ppは1100ボルト、1/2ルツクス・秒の結果
を埗た。 実斜䟋 52〜60 実斜䟋51においおNo.のゞスアゟ顔料の代りに
䞋蚘衚―のゞアゟ顔料を倫々甚いお同様な感光
䜓を䜜成した。これら感光䜓のpp及び1/2は
衚―の通りである。
[Table] Example 51 2 parts by weight of No. 1 disazo pigment and 98 parts by weight of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was applied onto an aluminum-deposited polyester film with a doctor blade and air-dried to form a thick film. A charge carrier generation layer having a thickness of 1 ÎŒm was formed. on the other hand,
2 parts by weight of 9-(4-diethylaminostyryl)anthracene, 2 parts by weight of polycarbonate (same as in Example 41) and 46 parts by weight of tetrahydrofuran were mixed and dissolved, and this was applied onto the charge carrier generation layer with a doctor blade. The layer was dried at 120° C. for 10 minutes to form a charge transport medium layer with a thickness of 10 Όm, thereby obtaining the laminated photoreceptor shown in FIG. Measurements were carried out in the same manner as in Example 1 except that -6 KV corona discharge was performed on the photoreceptor obtained as described above, and the results were as follows: V pp was 1100 volts and E 1/2 6 lux sec. Obtained. Examples 52 to 60 Photoreceptors similar to Example 51 were prepared using the diazo pigments shown in Table 6 below in place of the No. 1 disazo pigment. The V pp and E 1/2 of these photoreceptors are shown in Table 6.

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

第〜図は倫々䞀䟋の本発明感光䜓の拡倧断
面図、第図はNo.の赀倖線吞収スペクトルであ
る。   導電性支持䜓、′″  
感光局、  結着剀、  ゞスアゟ顔料、
  電荷移動媒䜓、  電荷担䜓発生局、 
 電荷移動媒䜓局。
1 to 4 are enlarged sectional views of one example of the photoreceptor of the present invention, and FIG. 5 is an infrared absorption spectrum of No. 1. 1... Conductive support, 2, 2', 2'', 2...
Photosensitive layer, 3... Binder, 4... Disazo pigment, 5
...Charge transport medium, 6...Charge carrier generation layer, 7...
...Charge transport medium layer.

Claims (1)

【特蚱請求の範囲】  導電性支持䜓䞊に、䞋蚘䞀般匏 䜆し匏䞭Arは眮換又は非眮換のプニル
基、眮換又は非眮換のナフチル基、アントリル
基、ピレニル基、ピリゞル基、チ゚ニル基、フリ
ル基及びカルバゟリル基を衚わす。で瀺される
ゞスアゟ顔料を有効成分ずしお含有する感光局を
有するこずを特城ずする電子写真甚感光䜓。
[Claims] 1. On a conductive support, the following general formula (However, in the formula, Ar represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, an anthryl group, a pyrenyl group, a pyridyl group, a thienyl group, a furyl group, and a carbazolyl group.) 1. A photoreceptor for electrophotography, characterized by having a photosensitive layer containing as a component.
JP17045679A 1979-12-28 1979-12-28 Electrophotographic receptor Granted JPS5694358A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP17045679A JPS5694358A (en) 1979-12-28 1979-12-28 Electrophotographic receptor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP17045679A JPS5694358A (en) 1979-12-28 1979-12-28 Electrophotographic receptor

Publications (2)

Publication Number Publication Date
JPS5694358A JPS5694358A (en) 1981-07-30
JPS6219743B2 true JPS6219743B2 (en) 1987-04-30

Family

ID=15905264

Family Applications (1)

Application Number Title Priority Date Filing Date
JP17045679A Granted JPS5694358A (en) 1979-12-28 1979-12-28 Electrophotographic receptor

Country Status (1)

Country Link
JP (1) JPS5694358A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5988449A (en) * 1982-11-12 1984-05-22 Ricoh Co Ltd Novel naphthol derivative compound and its preparation
JPS59196366A (en) * 1983-04-21 1984-11-07 Ricoh Co Ltd Novel trisazo compound and production thereof
JP3563916B2 (en) * 1996-04-26 2004-09-08 キダノン株匏䌚瀟 Electrophotographic photoreceptor, electrophotographic apparatus and process cartridge using the electrophotographic photoreceptor

Also Published As

Publication number Publication date
JPS5694358A (en) 1981-07-30

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