JP2569519B2 - Electrophotographic photoreceptor - Google Patents
Electrophotographic photoreceptorInfo
- Publication number
- JP2569519B2 JP2569519B2 JP62001590A JP159087A JP2569519B2 JP 2569519 B2 JP2569519 B2 JP 2569519B2 JP 62001590 A JP62001590 A JP 62001590A JP 159087 A JP159087 A JP 159087A JP 2569519 B2 JP2569519 B2 JP 2569519B2
- Authority
- JP
- Japan
- Prior art keywords
- charge
- charge transport
- layer
- agent
- charge generation
- 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 - Fee Related
Links
- 108091008695 photoreceptors Proteins 0.000 title claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000011669 selenium Substances 0.000 claims description 8
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 7
- 229910052711 selenium Inorganic materials 0.000 claims description 7
- 229920005668 polycarbonate resin Polymers 0.000 claims description 5
- 239000004431 polycarbonate resin Substances 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 4
- 230000000052 comparative effect Effects 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 6
- -1 hydrazone compounds Chemical class 0.000 description 5
- 239000002245 particle Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical class OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000007847 structural defect Effects 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- G03G5/06144—Amines arylamine diamine
- G03G5/061443—Amines arylamine diamine benzidine
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は電荷発生層、電荷輸送層とから成る機能分離
型電子写真感光体に係り、光感度や耐久性上に優れた特
性を有する電子写真感光体に関する。Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a function-separated electrophotographic photosensitive member comprising a charge generation layer and a charge transport layer, and has excellent characteristics in terms of photosensitivity and durability. About the body.
従来の技術 最近、有機光導電体を中心とした電子写真感光体につ
いて、それが低コストであるという長所を有することか
ら種々のものが提案されてきている。代表的な電荷発生
剤としてはジスアゾ顔料やフタロシアニン顔料などがあ
げられ、また、電荷輸送剤としては、ヒドラゾン化合
物、ピラゾリン化合物などがあげられ、それらは積層タ
イプの機能分離型電子写真感光体の構成成分として良く
用いられている。2. Description of the Related Art Recently, various types of electrophotographic photosensitive members, mainly organic photoconductors, have been proposed because of their low cost. Representative charge generating agents include disazo pigments and phthalocyanine pigments, and charge transporting agents include hydrazone compounds and pyrazoline compounds. Often used as a component.
特に電荷輸送剤として一般式（Ｉ）で示されるような
化合物は、特開昭53-27033号公報で記載されていること
からも明らかなように、非常に優れた電荷輸送特性を示
し、感度が高い電子写真感光体を形成する。In particular, the compound represented by the general formula (I) as a charge transporting agent exhibits extremely excellent charge transporting properties, as apparent from JP-A-53-27033, and To form an electrophotographic photoreceptor having a high
（R1及びR2はそれぞれＨまたはCH3を表わし、R3はCH3又
はClを表わす） 発明が解決しようとする問題点 しかしながら、前記の公報に記載の説明においても、
その感度は無機感光体（As2Se3やアモルファスシリコン
等）に比較した場合、未だ充分とはいえず、また、繰り
返し安定性に劣ることが明らかとなった。 (R 1 and R 2 each represent H or CH 3 , and R 3 represents CH 3 or Cl) Problems to be Solved by the Invention However, even in the description in the above-mentioned publication,
When compared with inorganic photoreceptors (such as As 2 Se 3 and amorphous silicon), the sensitivity was still not sufficient, and it was clarified that the repetition stability was poor.
したがって本発明の目的は、電荷発生剤として三方晶
系レセンを用い、電荷輸送剤として一般式（Ｉ）で示さ
れる化合物を用いた積層型電子写真感光体について、そ
の感度及び繰り返し安定性を、従来のものに比較し大幅
に改善することにある。すなわち、本発明の目的は、積
層型電子写真感光体の問題点のうち、特に感度及び繰り
返し安定性を大幅に改善した電子写真感光体を提供する
ことにある。Therefore, an object of the present invention is to provide a layered electrophotographic photoreceptor using a trigonal recene as a charge generating agent and a compound represented by the general formula (I) as a charge transporting agent. The point is to greatly improve compared with the conventional one. That is, an object of the present invention is to provide an electrophotographic photoreceptor having significantly improved sensitivity and repetition stability among the problems of the laminated electrophotographic photoreceptor.
問題点を解決するための手段 本発明者等は、従来法のもつ感度や繰り返し安定性を
さらに改善することを目的として一般式（Ｉ）で示され
る化合物について、従来の使用法とは異なる使用の仕方
を種々検討した結果、積層型の電子写真感光体において
三方晶系セレンを含む電荷発生層中にあらかじめ、一般
式（Ｉ）で示される極めて輸送性の高い電荷輸送剤を混
在させておくことにより、電子写真感光体の感度及び繰
り返し安定性が大きく改善されることを見出し、本発明
を完成するに至った。Means for Solving the Problems The inventors of the present invention have proposed a method of using a compound represented by the general formula (I) which is different from the conventional method for the purpose of further improving the sensitivity and the repetition stability of the conventional method. As a result of various investigations, a charge transporting agent having an extremely high transportability represented by the general formula (I) is mixed in advance in the charge generating layer containing trigonal selenium in the laminated electrophotographic photosensitive member. As a result, it has been found that the sensitivity and the repetition stability of the electrophotographic photosensitive member are greatly improved, and the present invention has been completed.
したがって、本発明は、導電性支持体上に、電荷発生
層および電荷輸送層を積層してなる電子写真感光体にお
いて、電荷輸送層は、下記一般式 （Ｉ） （式中、R1〜R3は前記と同意味を示す）で示される化合
物の１種又はそれ以上を下記一般式（II）及び（III） で表わされる単量体単位の１つ又は両者で構成されたポ
リカーボネート樹脂中に分散してなり、電荷発生層が、
電荷発生剤として三方晶系セレンを含有し、かつ、一般
式（Ｉ）で示される化合物の１種又はそれ以上を１〜30
重量％含有してなることを特徴とする。Accordingly, the present invention provides an electrophotographic photoreceptor comprising a charge generation layer and a charge transport layer laminated on a conductive support, wherein the charge transport layer has the following general formula (I) (Wherein R 1 to R 3 have the same meanings as described above), and one or more of the compounds represented by the following general formulas (II) and (III) Is dispersed in a polycarbonate resin composed of one or both of the monomer units represented by
It contains trigonal selenium as a charge generating agent, and one or more of the compounds represented by the general formula (I) is 1 to 30.
% By weight.
本発明の電子写真感光体を図面によって説明すると、
第１図及び第２図はそれぞれ本発明の電子写真感光体の
基本的構成を示す模式図である。The electrophotographic photosensitive member of the present invention will be described with reference to the drawings.
FIG. 1 and FIG. 2 are schematic diagrams each showing a basic configuration of the electrophotographic photosensitive member of the present invention.
第１図においては、導電性支持体１上に、電荷発生層
２及び電荷輸送層３が順次積層されており、第２図にお
いては、導電性支持体１上に電荷輸送層３及び電荷発生
層２が順次積層されている。In FIG. 1, a charge generation layer 2 and a charge transport layer 3 are sequentially laminated on a conductive support 1. In FIG. 2, the charge transport layer 3 and the charge generation layer 3 are formed on the conductive support 1. The layers 2 are sequentially stacked.
本発明の電子写真感光体を構成する各層について説明
する。Each layer constituting the electrophotographic photosensitive member of the present invention will be described.
本発明の電子写真感光体において、電荷輸送層は、電
荷輸送剤として、前記一般式（Ｉ）で示される化合物を
１種又はそれ以上組み合わせて使用する。In the electrophotographic photoreceptor of the invention, the charge transport layer uses, as a charge transport agent, one or more compounds represented by the above general formula (I) in combination.
本発明においては、結着樹脂として前記一般式（II）
及び（III）のいずれか又は両者を単量体単位といて構
成されるポリカーボネート樹脂が用いられる。これらポ
リカーボネートについては「プラスチック材料講座５ポ
リカーボネート樹脂」（日刊工業新聞社 昭和44年発
行）に詳しく記載されており、例えば、ポリ（4,4′−
イソプロピリデン−ジフェニレンカーボネート）、ポリ
（4,4′−シクロヘキシリデン−ジフェニレンカーボネ
ート）などがあげられる。In the present invention, the binder resin represented by the general formula (II)
A polycarbonate resin composed of one or both of (III) and (III) as a monomer unit is used. These polycarbonates are described in detail in "Plastic Materials Course 5 Polycarbonate Resin" (published by Nikkan Kogyo Shimbun, 1969). For example, poly (4,4'-
Isopropylidene-diphenylene carbonate) and poly (4,4'-cyclohexylidene-diphenylene carbonate).
本発明において、結着樹脂としては、上記ポリカーボ
ネート樹脂と共に、他の皮膜形成性樹脂を併用してもよ
い。In the present invention, as the binder resin, another film-forming resin may be used in combination with the polycarbonate resin.
そのような樹脂としては、ポリアリレート、ポリエス
テル、ポリスチレン、スチレン−アクリロニトリル共重
合体、ポリサルホン、ポリメタクリレート、スチレン−
メタクリレート共重合体、その他のビニル重合体などが
あげられる。Such resins include polyarylate, polyester, polystyrene, styrene-acrylonitrile copolymer, polysulfone, polymethacrylate, styrene-
Examples include methacrylate copolymers and other vinyl polymers.
前記電荷輸送剤が電荷輸送層中に占める割合は10〜75
重量％が好ましく、より好ましくは35〜60重量％であ
る。上記範囲よりも多く含有する場合には、電荷輸送層
の機械的強度が低下し、少なすぎる場合には感度が低下
する。The ratio of the charge transport agent in the charge transport layer is 10 to 75.
% By weight, more preferably 35 to 60% by weight. When the content is more than the above range, the mechanical strength of the charge transport layer is reduced, and when it is too small, the sensitivity is reduced.
また、電荷輸送層の膜厚は２〜100μｍ好ましくは10
〜30μｍである。The charge transport layer has a thickness of 2 to 100 μm, preferably 10 to 100 μm.
3030 μm.
電荷輸送層は、前述の電荷輸送剤と結着樹脂とを適当
な溶媒に溶解せしめた溶液を塗布し、乾燥せしめること
により形成させることが好ましい。The charge transport layer is preferably formed by applying a solution obtained by dissolving the above-described charge transport agent and the binder resin in an appropriate solvent, followed by drying.
また、電荷輸送層を形成させる際に用いる溶媒として
は、多数の有用な有機溶媒があげられる。その代表的な
ものとして、例えばベンゼン、トルエン、キシレン、メ
シチレン、クロロベンゼンなどの芳香族系炭化水素類、
アセトン、２−ブタノンなどのケトン類、塩化メチレ
ン、クロロホルム、塩化エチレンなどのハロゲン化脂肪
族系炭化水素類、テトラヒドロフラン、ジオキサン、エ
チレングリコール、ジエチルエーテルなどの環状若しく
は、直鎖状のエーテル類など、あるいは、これらの混合
溶媒をあげることができる。Examples of the solvent used for forming the charge transport layer include many useful organic solvents. As typical ones, for example, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, chlorobenzene,
Acetone, ketones such as 2-butanone, methylene chloride, chloroform, halogenated aliphatic hydrocarbons such as ethylene chloride, tetrahydrofuran, dioxane, ethylene glycol, and cyclic or linear ethers such as diethyl ether; Alternatively, a mixed solvent thereof can be used.
本発明の電子写真感光体において、電荷発生層は、電
荷発生剤である三方晶系セレンと共にさらに電荷輸送剤
である前記一般式（Ｉ）で示される化合物の１種又はそ
れ以上を含有する点に特徴を有する。In the electrophotographic photoreceptor of the present invention, the charge generation layer further contains one or more of the compound represented by the general formula (I) as a charge transport agent, together with trigonal selenium as a charge generator. It has features.
本発明において、電荷輸送剤、即ち前記一般式（Ｉ）
で表される化合物の電荷発生層中に占める割合は、１〜
30重量％であり、好ましく１〜10重量％である。電荷輸
送剤の量が少なすぎる場合には、所望の特性を得ること
ができない。逆に多すぎる場合には、三方晶セレンの電
荷発生機能に悪影響を及ぼし、感度低下を招いたり、ま
た、電荷発生層の機械的強度が著しく低下し、ハガレ等
が生じるといったような２次障害が発生する。In the present invention, the charge transport agent, that is, the above-mentioned general formula (I)
The proportion of the compound represented by in the charge generation layer is from 1 to
It is 30% by weight, preferably 1 to 10% by weight. If the amount of the charge transporting agent is too small, desired characteristics cannot be obtained. On the other hand, when the amount is too large, it adversely affects the charge generation function of the trigonal selenium, causing a reduction in sensitivity, and also causes a mechanical failure of the charge generation layer to be remarkably reduced, resulting in secondary damage such as peeling. Occurs.
電荷発生層中に混在させる電荷輸送剤の種類は電荷輸
送層中に用いているものと一致させることが好ましい。
しかしながら、電荷輸送剤が一般式（Ｉ）で表わされる
範囲のものであれば、電荷発生層及び電荷輸送層のそれ
ぞれに互いに異なる種類の電荷輸送剤を含ませても、特
性的に大きな差は見られないので差し支えない。It is preferable that the kind of the charge transport agent mixed in the charge generation layer is the same as that used in the charge transport layer.
However, as long as the charge transporting agent is in the range represented by the general formula (I), even if the charge generating layer and the charge transporting layer each include a different type of charge transporting agent, there is a large difference in characteristics. You can't see it.
本発明において、電荷発生層における結着樹脂として
は、疎水性でかつ誘電率が高く、電気絶縁性のフイルム
形成性高分子重合体を用いるのが好ましい。In the present invention, as the binder resin in the charge generation layer, it is preferable to use a film-forming polymer polymer which is hydrophobic, has a high dielectric constant, and is electrically insulating.
このような高分子重合体としては、例えば次のものを
あげることができるが、これらに限定されるものではな
い。Examples of such a high-molecular polymer include, but are not limited to, the following.
ポリカーボネート、ポリエステル、メタクリル樹脂、
アクリル樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、
ポリスチレン、ポリビニルアセテート、スチレン−ブタ
ジエン共重合体、塩化ビニリデン−アクリロニトリル共
重合体、塩化ビニル−酢酸ビニル共重合体、塩化ビニル
−酢酸ビニル−無水マレイン酸共重合体、シリコン樹
脂、シリコン−アルキッド樹脂、フエノール−ホルムア
ルデヒド樹脂、スチレン−アルキッド樹脂、ポリ−Ｎ−
ビニルカルバゾール。Polycarbonate, polyester, methacrylic resin,
Acrylic resin, polyvinyl chloride, polyvinylidene chloride,
Polystyrene, polyvinyl acetate, styrene-butadiene copolymer, vinylidene chloride-acrylonitrile copolymer, vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, silicone resin, silicon-alkyd resin, Phenol-formaldehyde resin, styrene-alkyd resin, poly-N-
Vinyl carbazole.
これらの結着樹脂は、単独であるいは２種以上の混合
物として用いることができる。These binder resins can be used alone or as a mixture of two or more.
電荷発生層の膜厚は、２μｍ以下が望ましく、より好
ましくは0.01〜１μｍである。The thickness of the charge generation layer is preferably 2 μm or less, more preferably 0.01 to 1 μm.
作用 本発明の電子写真感光体の感度及び繰り返し安定性が
改善される理由は、次のような作用によると考えられ
る。The reason why the sensitivity and the repetition stability of the electrophotographic photoreceptor of the present invention are improved is considered to be as follows.
電荷発生層中の電荷発生剤である三方晶セレンに光が
あたり、キャリアが発生すると、キャリアは電荷発生剤
の粒子内及び粒子間を移動し、最終的に電荷輸送剤にキ
ャリアを受け渡すことになる。しかしながら、一般に電
荷発生剤粒子間には、構造欠陥や結着材や不純物などの
バリヤ（障壁）が生じやすく、キャリアの移動は必ずし
も速くない。これに対し、本発明のように、電荷発生層
中に電荷輸送剤を前もって意図的に混在させてやると、
個々の電荷発生剤の周囲に多数の電荷輸送剤が存在する
状態になり、電荷発生剤により発生したキャリアは、す
ばやく粒子界面に存在する電荷輸送剤に注入され、電荷
発生層中を電荷輸送剤を通して移動でき、最終的に電荷
輸送層へのキャリア移動がスムースに行なわれることに
なる。したがって、電荷輸送性が向上した分、見かけ上
感度は増加することになる。When light strikes the trigonal selenium, which is the charge generating agent in the charge generating layer, and the carrier is generated, the carrier moves inside and between the particles of the charge generating agent, and finally passes the carrier to the charge transporting agent. become. However, generally, a barrier such as a structural defect, a binder, or an impurity is easily generated between the charge generating particles, and the movement of the carrier is not always fast. On the other hand, as in the present invention, when the charge transport agent is intentionally mixed in advance in the charge generation layer,
A large number of charge transporting agents exist around each charge generating agent, and the carriers generated by the charge generating agent are quickly injected into the charge transporting agent present at the particle interface, and travel through the charge generating layer. , And finally the carrier moves smoothly to the charge transport layer. Therefore, the sensitivity is apparently increased due to the improvement of the charge transporting property.
また、従来の電子写真感光体においては、それを繰り
返し使用することにより、電荷発生剤の粒子界面におい
て、前記のようなバリヤが、キャリアのトラップ・サイ
ト（捕獲中心）となりやすく、その分、電荷発生層中に
空間電荷が溜りやすくなり、電子写真感光体の繰り返し
安定性が極めて悪くなる。ところが、本発明の如く、電
荷発生層中に電荷輸送剤を混在させるとキャリア移動が
スムースに行われるためトラップ・サイトは形成されに
くくなる。また、トラップ・サイトが存在してもキャリ
ア移動は電荷輸送剤を経ることによって影響を受けにく
くなる。Further, in the conventional electrophotographic photoreceptor, by repeatedly using the photoreceptor, the above-described barrier easily becomes a trap site (capture center) of the carrier at the particle interface of the charge generating agent. Space charges easily accumulate in the generation layer, and the repetition stability of the electrophotographic photosensitive member becomes extremely poor. However, when a charge transport agent is mixed in the charge generation layer as in the present invention, carrier transfer is performed smoothly, so that trap sites are hardly formed. In addition, even if trap sites are present, carrier movement is less affected by passing through the charge transport agent.
実施例 以下、本発明を実施例に従って具体的に説明するが、
これにより本発明が限定されるものではない。Examples Hereinafter, the present invention will be described specifically with reference to Examples.
This does not limit the present invention.
三方晶系セレン24重量部と、フェノキシ樹脂（ユニオ
ン・カーバイド社製、グレードPKHH）６重量部をテトラ
ヒドロフラン300重量部に溶かした溶液とを混合し、ボ
ールミルで20時間分散した後、この分散液に２重量部の
下記電荷輸送剤 を加え、約１時間攪拌した。ワイヤバーを用いて導電性
支持体（100μｍ厚さのAlシート）上に塗布、乾燥して
厚さ約0.3μｍの電荷発生層を形成させた。次に電荷発
生層の上に上記の電荷輸送剤10重量部と、下記の単量体
単位よりなるポリ（4,4′−シクロヘキシリデン−ジフ
ェニレンカーボネート）であるポリカーボネートＺ 10重量部とをモノクロルベンゼン90重量部に溶解した溶
液をワイヤバーを用いて塗布、乾燥して厚さ約20μｍの
電荷輸送層を形成させ、２層からなる電子写真感光層を
有する電子写真感光体を作製した。A mixture of 24 parts by weight of trigonal selenium and 6 parts by weight of a phenoxy resin (manufactured by Union Carbide Co., Ltd., grade PKHH) dissolved in 300 parts by weight of tetrahydrofuran was mixed and dispersed in a ball mill for 20 hours. 2 parts by weight of the following charge transport agent Was added and stirred for about 1 hour. It was applied on a conductive support (100 μm thick Al sheet) using a wire bar and dried to form a charge generation layer having a thickness of about 0.3 μm. Next, on the charge generation layer, 10 parts by weight of the above-mentioned charge transporting agent and polycarbonate Z which is poly (4,4'-cyclohexylidene-diphenylene carbonate) comprising the following monomer units An electrophotographic photosensitive member having a two-layer electrophotographic photosensitive layer by applying a solution obtained by dissolving 10 parts by weight in 90 parts by weight of monochlorobenzene using a wire bar and drying to form a charge transport layer having a thickness of about 20 μm Was prepared.
この電子写真感光体を円筒状シリンダーに貼りつけて
これを複写機（富士ゼロックス（株）製3500を改造した
もの）に装着した。この複写機は、シリンダーの周囲に
負極性帯電器、露光光学系、除電光学系等を配置してお
り、シリンダーの回転に伴ない、順次各工程の操作が繰
り返し行われ、そして電子写真感光体の表面電位をシリ
ンダー周りの数ケ所で測定することができるようになっ
ている。This electrophotographic photoreceptor was attached to a cylindrical cylinder and mounted on a copying machine (a modified version of Fuji Xerox Co., Ltd. 3500). In this copier, a negative charger, an exposure optical system, a static elimination optical system, and the like are arranged around a cylinder, and the operations of the respective steps are repeatedly performed sequentially with the rotation of the cylinder. Can be measured at several points around the cylinder.
この実施例の電子写真感光体の帯電特性を第１表に示
す。Table 1 shows the charging characteristics of the electrophotographic photosensitive member of this example.
比較例１ 実施例において電荷発生層中に電荷輸送剤を添加させ
ないこと以外は、実施例と同様にして、電子写真感光体
を作製した。Comparative Example 1 An electrophotographic photoreceptor was produced in the same manner as in the example, except that the charge transporting agent was not added to the charge generation layer.
比較例２ 実施例において電荷発生層及び電荷輸送層に添加すべ
き電荷輸送剤を、実施例の化合物の替わりに下記ヒドラ
ゾン化合物 を添加したこと以外は、実施例と同様にして、電子写真
感光体を作製した。Comparative Example 2 The following hydrazone compound was used in place of the compound of the example, except that the charge transporting agent to be added to the charge generation layer and the charge transporting layer in the example was changed. An electrophotographic photoreceptor was produced in the same manner as in Example except that was added.
比較例３ 比較例２において、電荷発生層中には前記ヒドラゾン
化合物を添加せず、電荷輸送層中にのみ、比較例２と同
一のヒドラゾン化合物を電荷輸送剤として用い、同様に
して電子写真感光体を作製した。Comparative Example 3 In Comparative Example 2, the same hydrazone compound as Comparative Example 2 was used as a charge transport agent only in the charge transport layer without adding the hydrazone compound to the charge generation layer. The body was made.
比較例４ 下記構造式 で示されるスクエアリン酸誘導体:2,4−ビス−（２−メ
チル−４−ジエチルアミノフェニル）−1,3−シクロブ
タジエン−ジイリウム−1,3−ジオレート24重量部に、
ポリエステル樹脂（デュポン社製、アドヘッシブ4900
0）６重量部、テトラヒドロフラン100重量部を加え、ボ
ールミルで20時間分散し、得られた分散液中に、下記構
造式で示される電荷輸送剤 ２重量部を加え、約１時間撹拌した。Comparative Example 4 The following structural formula Squaric acid derivative represented by: 2,4-bis- (2-methyl-4-diethylaminophenyl) -1,3-cyclobutadiene-diylium-1,3-diolate 24 parts by weight,
Polyester resin (Adhesive 4900 manufactured by DuPont)
0) 6 parts by weight of tetrahydrofuran and 100 parts by weight of tetrahydrofuran were added, and the mixture was dispersed in a ball mill for 20 hours. 2 parts by weight were added and stirred for about 1 hour.
得られた電荷発生層形成用塗布液を用いた以外は、前
記実施例１と同様にして、導電性支持体上に電荷発生
層、電荷輸送層を順次形成し、電子写真感光体を作製し
た。この電子写真感光体について、前記実施例と同様に
して評価を行った。その結果を第１表に示す。Except for using the obtained coating solution for forming a charge generation layer, a charge generation layer and a charge transport layer were sequentially formed on a conductive support in the same manner as in Example 1 to prepare an electrophotographic photosensitive member. . This electrophotographic photosensitive member was evaluated in the same manner as in the above example. Table 1 shows the results.
比較例５ 比較例４において、電荷発生層形成用塗布液に電荷輸
送剤を含有させなかった以外は比較例４と同様にして電
子写真感光体を作製した。この電子写真感光体につい
て、前記実施例と同様にして評価を行った。その結果を
第１表に示す。Comparative Example 5 An electrophotographic photosensitive member was prepared in the same manner as in Comparative Example 4, except that the charge transport layer was not contained in the coating solution for forming a charge generating layer. This electrophotographic photosensitive member was evaluated in the same manner as in the above example. Table 1 shows the results.
発明の効果 本発明の電子写真感光体は、前記の構成を有するか
ら、上記実施例及び比較例から明らかなように優れた感
度を有し、また、繰り返し使用した場合の安定性におい
ても優れている。 Effects of the Invention Since the electrophotographic photoreceptor of the present invention has the above-described configuration, it has excellent sensitivity as is clear from the above Examples and Comparative Examples, and also has excellent stability when used repeatedly. I have.
本発明の電子写真感光体は電子写真複写機のほか、ゼ
ログラフィー技術を応用した各種のプリンター、マイク
ロフイルムリーダー、電子写真製版システムなどにも広
く用いることができる。The electrophotographic photoreceptor of the present invention can be widely used for various printers, microfilm readers, electrophotographic plate making systems and the like to which xerography technology is applied, in addition to electrophotographic copying machines.
第１図及び第２図は、それぞれ本発明の電子写真感光体
の基本的な構成を示す模式図である。 １……導電性支持体、２……電荷発生層、３……電荷輸
送層。FIG. 1 and FIG. 2 are schematic diagrams each showing a basic configuration of the electrophotographic photosensitive member of the present invention. 1 ... conductive support, 2 ... charge generation layer, 3 ... charge transport layer.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭61−62038（ＪＰ，Ａ) 特開 昭61−62039（ＪＰ，Ａ) 特開 昭55−79450（ＪＰ，Ａ) 特開 昭61−105550（ＪＰ，Ａ) 特開 昭61−124949（ＪＰ，Ａ) 特開 昭56−35140（ＪＰ，Ａ) ──────────────────────────────────────────────────続 き Continuation of front page (56) References JP-A-61-62038 (JP, A) JP-A-61-62039 (JP, A) JP-A-55-79450 (JP, A) JP-A-61-62038 105550 (JP, A) JP-A-61-124949 (JP, A) JP-A-56-35140 (JP, A)
Claims (1)
輸送層を積層してなる電子写真感光体において、電荷輸
送層は、下記一般式（Ｉ） （R1及びR2はそれぞれＨまたはCH3を表わし、R3はCH3又
はClを表わす） で示される化合物の１種又はそれ以上を下記一般式（I
I）及び（III） で示される単量体単位の１つ又は両者で構成されたポリ
カーボネート樹脂中に分散してなり、電荷発生層は、電
荷発生剤として三方晶系セレンを含有し、かつ、一般式
（Ｉ）で表される化合物の１種又はそれ以上を１〜30重
量％含有してなることを特徴とする電子写真感光体。1. An electrophotographic photoreceptor comprising a charge generation layer and a charge transport layer laminated on a conductive support, wherein the charge transport layer has the following general formula (I) (R 1 and R 2 each represent H or CH 3 , and R 3 represents CH 3 or Cl) One or more compounds represented by the following general formula (I)
I) and (III) Wherein the charge generation layer contains trigonal selenium as a charge generation agent, and is dispersed in a polycarbonate resin composed of one or both of the monomer units represented by the general formula (I). An electrophotographic photosensitive member comprising 1 to 30% by weight of one or more compounds represented by the formula.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62001590A JP2569519B2 (en) | 1987-01-09 | 1987-01-09 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62001590A JP2569519B2 (en) | 1987-01-09 | 1987-01-09 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63278065A JPS63278065A (en) | 1988-11-15 |
| JP2569519B2 true JP2569519B2 (en) | 1997-01-08 |
Family
ID=11505725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62001590A Expired - Fee Related JP2569519B2 (en) | 1987-01-09 | 1987-01-09 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2569519B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4988595A (en) * | 1989-12-18 | 1991-01-29 | Xerox Corporation | Charge transport layer containing different aromatic diamine active charge transport compounds |
| JP5540687B2 (en) | 2009-12-18 | 2014-07-02 | コニカミノルタ株式会社 | Electrophotographic photoreceptor, image forming method and image forming apparatus |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4306008A (en) * | 1978-12-04 | 1981-12-15 | Xerox Corporation | Imaging system with a diamine charge transport material in a polycarbonate resin |
| JPS6162039A (en) * | 1984-09-04 | 1986-03-29 | Fuji Xerox Co Ltd | Electrophotografic sensitive body |
| JPS6162038A (en) * | 1984-09-04 | 1986-03-29 | Fuji Xerox Co Ltd | Electrophotografic sensitive body |
| JPS61105550A (en) * | 1984-10-29 | 1986-05-23 | Fuji Xerox Co Ltd | Electrophotographic sensitive body |
-
1987
- 1987-01-09 JP JP62001590A patent/JP2569519B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63278065A (en) | 1988-11-15 |
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