JPH0212257A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0212257A JPH0212257A JP16301988A JP16301988A JPH0212257A JP H0212257 A JPH0212257 A JP H0212257A JP 16301988 A JP16301988 A JP 16301988A JP 16301988 A JP16301988 A JP 16301988A JP H0212257 A JPH0212257 A JP H0212257A
- Authority
- JP
- Japan
- Prior art keywords
- group
- groups
- photoreceptor
- formulas
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- -1 azo compound Chemical class 0.000 abstract description 25
- 239000000463 material Substances 0.000 abstract description 25
- 229920005989 resin Polymers 0.000 abstract description 14
- 239000011347 resin Substances 0.000 abstract description 14
- 239000011230 binding agent Substances 0.000 abstract description 12
- 239000000758 substrate Substances 0.000 abstract description 12
- 238000007600 charging Methods 0.000 abstract description 10
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 9
- 239000011247 coating layer Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- YGBCLRRWZQSURU-UHFFFAOYSA-N 4-[(diphenylhydrazinylidene)methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 YGBCLRRWZQSURU-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- DGVZQSMXUHGJHU-UHFFFAOYSA-N 1,2-dinitrofluoren-9-one Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C2=C1 DGVZQSMXUHGJHU-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 1
- 101100295091 Arabidopsis thaliana NUDT14 gene Proteins 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229910001370 Se alloy Inorganic materials 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000011787 zinc oxide 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
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0679—Disazo dyes
- G03G5/0681—Disazo dyes containing hetero rings in the part of the molecule between the azo-groups
-
- 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
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0679—Disazo dyes
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
この発明は電子写真用感光体に関し、詳しくは導電性基
体上に形成した感光層の中に、前記一般式(I)で示さ
れるアゾ化合物を含有することを特徴とする電子写真用
感光体に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more specifically, an azo compound represented by the general formula (I) is contained in a photosensitive layer formed on a conductive substrate. The present invention relates to an electrophotographic photoreceptor characterized by containing the following.
従来より電子写真用感光体(以下感光体とも称する]の
感光材料としてはセレンまたはセレン合金などの無機光
導電性物質、酸化亜鉛あるいは硫化カドミウムなどの無
機光導電性物質を樹脂結着剤中に分散させたもの、ポリ
−N−ビニルカルバゾールまたはポリビニルアントラセ
ンなどの有機光導電性物質、フタロシアニン化合物ある
いはビスアゾ化合物などの有機光導電性物質、あるいは
これら有機光導電性物質を樹脂結着剤中に分散させたも
のなどが利用されている。Conventionally, photosensitive materials for electrophotographic photoreceptors (hereinafter also referred to as photoreceptors) include inorganic photoconductive substances such as selenium or selenium alloys, or inorganic photoconductive substances such as zinc oxide or cadmium sulfide in a resin binder. dispersion, organic photoconductive materials such as poly-N-vinylcarbazole or polyvinylanthracene, organic photoconductive materials such as phthalocyanine compounds or bisazo compounds, or dispersion of these organic photoconductive materials in a resin binder. Those that have been made are used.
また、感光体には暗所で表面電荷を保持する機能、光を
受容して電荷を発生する機能、同じく光を受容して電荷
を輸送する機能とが必要であるが、一つの層でこれらの
機能をあわせもったいわゆる単層型感光体と、主として
電荷発生に寄与する層と暗所での表面電荷の保持と光受
容時の電荷輸送に寄与する層とに機能分離した層を積層
したいわゆる積層型感光体がある。これらの感光体を用
いた電子写真法による画像形成には、例えばカールソン
方式が適用される。この方式での画像形成は暗所での感
光体へのコロナ放電による帯電、帯電された感光体表面
上への露光による原稿の文字や絵などの静電潜像の形成
、形成された静電潜像のトナーによる現像、現像された
トナー像の紙などの支持体への転写、定着により行われ
、トナー像転写後の感光体は除電、残留トナーの除去、
光除電などを行った後、再使用に供される。In addition, a photoreceptor must have the function of retaining surface charge in the dark, the function of receiving light and generating charge, and the function of receiving light and transporting charge, all of which can be achieved in one layer. A so-called single-layer photoreceptor with the following functions is laminated with functionally separated layers: a layer that mainly contributes to charge generation, and a layer that contributes to surface charge retention in the dark and charge transport during light reception. There is a so-called laminated photoreceptor. For example, the Carlson method is applied to image formation by electrophotography using these photoreceptors. Image formation in this method involves charging the photoconductor in a dark place by corona discharge, forming electrostatic latent images such as letters and pictures on the document by exposing the surface of the charged photoconductor, and This is done by developing the latent image with toner, transferring the developed toner image to a support such as paper, and fixing it. After the toner image is transferred, the photoreceptor is charged, the residual toner is removed,
After photostatic charge removal, etc., it is reused.
近年、可とう性、熱安定性、膜形成性などの利点により
、有機材料を用いた電子写真用感光体が実用化されてき
ている。例えば、ポU −N−ビニルカルバゾールと2
.4.7−)ジニトロフルオレン−9−オンとからなる
感光体く米国特許第3484237号明細書に記載)、
有機顔料を主成分とする感光体(特開昭47−3754
3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)などである。さらに、新規アゾ化合物、ペリレン化
合物も多く実用化されている。In recent years, electrophotographic photoreceptors using organic materials have been put into practical use due to their advantages such as flexibility, thermal stability, and film-forming properties. For example, poly-N-vinylcarbazole and 2
.. 4.7-) dinitrofluoren-9-one (described in US Pat. No. 3,484,237),
Photoreceptor containing organic pigment as main component (Japanese Patent Application Laid-Open No. 47-3754
3), and a photoreceptor whose main component is a eutectic complex consisting of a dye and a resin (described in JP-A-47-10735). Furthermore, many new azo compounds and perylene compounds have been put into practical use.
上述のように、有機材料は無機材料にない多くの長所を
持つが、しかしながら、電子写真用感光体に要求される
すべての特性を充分に満足するものがまだ得られていな
いのが現状であり、特に光感度および繰り返し連続使用
時の特性に問題があった。As mentioned above, organic materials have many advantages that inorganic materials do not have, but at present, no material has yet been obtained that fully satisfies all the characteristics required of electrophotographic photoreceptors. In particular, there were problems with photosensitivity and characteristics during repeated and continuous use.
この発明は、上述の点に鑑みてなされたものであって、
感光層に電荷発生物質として今まで用いられたことのな
い新しい有機材料を用いることにより、高感度で繰り返
し特性の優れた電子写真用感光体を提供することを目的
とする。This invention was made in view of the above points, and
An object of the present invention is to provide an electrophotographic photoreceptor with high sensitivity and excellent repeatability by using a new organic material that has never been used as a charge generating substance in the photosensitive layer.
上記目的を達成するために、この発明によれば、下記一
般式(Hに示した化合物のうちの少なくとも一種類を含
む感光層を備えた電子写真用感光体とする。In order to achieve the above object, the present invention provides an electrophotographic photoreceptor including a photosensitive layer containing at least one compound represented by the following general formula (H).
〔式(I)中、Ar、およびAr2は以下のそれぞれ置
換されていてもよい芳香族炭化水素基、芳香族複素環基
のうちのいずれかを表しくただし、同時に置換もしくは
未置換のフェニレン基になることはない)、Cρはカッ
プラー残基を表す。〕上記一般式(I)におけるCρ(
カップラー残基)としては、下記一般式(II)ないし
(V)で示される構造のものが好適である。[In formula (I), Ar and Ar2 each represent any of the following optionally substituted aromatic hydrocarbon groups and aromatic heterocyclic groups, provided that at the same time, a substituted or unsubstituted phenylene group ), Cρ represents a coupler residue. ] Cρ( in the above general formula (I)
As the coupler residue, those having structures represented by the following general formulas (II) to (V) are suitable.
〔式(n)ないし(V)において、Zはベンゼン環と縮
合して多環芳香環あるいは複素瓜を形成する残基を表し
、xlはOR,もしく ハN R2R−(R3゜R3お
よびR3は水素原子、または以下のそれぞれ置換されて
いてもよいアルキル基、アリール基。[In formulas (n) to (V), Z represents a residue that is condensed with a benzene ring to form a polycyclic aromatic ring or a heterozygote, xl is OR, or HN R2R-(R3゜R3 and R3 is a hydrogen atom, or each of the following optionally substituted alkyl or aryl groups.
芳香族複素環基のうちのいずれかを表す)を表し、X2
およびX、は以下のそれぞれ置換されていてもよいアル
キル基、アリール基、芳香族複素環基のうちのいずれか
を表し、X3′J6よびX、は水素原子。represents any aromatic heterocyclic group), and X2
and X represent any of the following optionally substituted alkyl groups, aryl groups, and aromatic heterocyclic groups, and X3'J6 and X are hydrogen atoms.
シアノ基、カルバモイル基、カルボキシル基、エステル
基、アシル2.(のうちのいずれかを表し、X、は水素
原子、または以下のそれぞれ置換されていてもよいアル
キル基、シクロアルキル基、アルケニル基、アリール基
、芳香族複素環基のうちのいずれかを表し、X、および
χBは水素原子、ハロゲン原子、ニトロ基、または以下
のそれぞれ置換されていてもよいアルキル基、アルコキ
シ基のうちのいずれかを表し、X9 はアルキル基、ア
リール基、カルボキシル基、エステル基のうちのいずれ
かを表し、xl。はそれぞれ置換されていてもよいアリ
ール基、芳香族複素環基のうちのいずれかを表す。〕
この発明に用いられる前記一般式(I)のアゾ化合物は
、それぞれ対応するジアゾニウム塩とカップラーを、適
当な有機溶媒9例えばN、N−ジメチルホルムアミド(
DMF)中で塩基を作用させて、カップリング反応させ
ることにより合成することができる。Cyano group, carbamoyl group, carboxyl group, ester group, acyl2. (X represents a hydrogen atom, or any of the following optionally substituted alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, and aromatic heterocyclic groups) , X, and χB represent a hydrogen atom, a halogen atom, a nitro group, or each of the following optionally substituted alkyl groups and alkoxy groups; represents any one of the groups, and xl. represents either an optionally substituted aryl group or an aromatic heterocyclic group.] Azo compound of the general formula (I) used in this invention are the respective corresponding diazonium salts and couplers in a suitable organic solvent 9 such as N,N-dimethylformamide (
It can be synthesized by reacting with a base in DMF) to cause a coupling reaction.
こうして得られる前記一般式(I)のアゾ化合物の具体
例を示すと、次の通りである。Specific examples of the azo compound of the general formula (I) thus obtained are as follows.
1j
〔作用〕
前記一般式(+)で示されるアゾ化合物を感光層に用い
た例は知られていない。本発明者らは前記目的を達成す
るために各種有機材料について鋭意検討を進めるなかで
、これらアゾ化合物について数多くの実験を行った結果
、その技術的解明はまだ充分なされてはいないが、この
ような前記一般式(+)で示される特定のアゾ化合物を
電荷発生物質として使用することが、電子写真特性の向
上に場めて有効であることを見出し、高感度で繰り返し
特性の優れた感光体を得るに至ったのである。1j [Function] There is no known example of using an azo compound represented by the above general formula (+) in a photosensitive layer. In order to achieve the above object, the present inventors conducted a number of experiments on these azo compounds while conducting intensive studies on various organic materials. It has been discovered that the use of a specific azo compound represented by the above general formula (+) as a charge-generating substance is effective in improving electrophotographic properties, and a photoreceptor with high sensitivity and excellent repeatability has been developed. I was able to obtain this.
この発明の感光体は、前記一般式(I)で示されるアブ
化合物を感光層中に含有させたものであるが、これらア
ゾ化合物の応用の仕方によって、第1図、第2図、ある
いは第3図に示したごとくに用いることができる。The photoreceptor of the present invention contains an azo compound represented by the general formula (I) in the photosensitive layer, and depending on how these azo compounds are applied, the photoreceptor may have a photoreceptor shown in FIG. 1, FIG. 2, or FIG. It can be used as shown in Figure 3.
第1図〜第3図はこの発明の感光体のそれぞれ異なる実
施例の概念的断面図で、lは導電性基体、2a、2b、
2cは感光層、3は電荷発生物質、4は電荷発生層、5
は電荷輸送物質、6は電荷輸送層、7は被覆層である。FIGS. 1 to 3 are conceptual cross-sectional views of different embodiments of the photoreceptor of the present invention, where l is a conductive substrate, 2a, 2b,
2c is a photosensitive layer, 3 is a charge generating material, 4 is a charge generating layer, 5
6 is a charge transporting material, 6 is a charge transporting layer, and 7 is a coating layer.
第1図は、導電性基体1上に電荷発生物質3である前記
一般式(I)で示されるアゾ化合物と電荷輸送物質5を
樹脂バインダー(結着剤)中に分散した感光層2a(通
常単層型感光体と称せられる構成)が設けられたもので
ある。FIG. 1 shows a photosensitive layer 2a (usually The structure is called a single-layer photoreceptor).
第2図は、導電性基体l上に電荷発生物質3である前記
一般式N)で示されるアゾ化合物を含有する電荷発生層
4と、電荷輸送物質5を主体とする電荷輸送層6との積
層からなる感光層2b(通常積層型感光体と称せられる
構成)が設けられたものである。この構成の感光体は通
常負帯電方式%式%
第3図は、第2図の逆の層構成の感光層2cが設けられ
たものであり、通常正帯電方式で用いられる。この場合
には、電荷発生層4を保護するために、さらに被覆層7
を設けるのが一般的である。FIG. 2 shows a charge-generating layer 4 containing an azo compound represented by the general formula N) as a charge-generating substance 3 and a charge-transporting layer 6 mainly composed of a charge-transporting substance 5 on a conductive substrate 1. A photosensitive layer 2b (commonly referred to as a laminated type photoreceptor) consisting of a laminated layer is provided. A photoreceptor having this structure is normally used in a negative charging method. FIG. 3 shows a photosensitive layer 2c having a layer structure opposite to that in FIG. 2, and is normally used in a positive charging method. In this case, in order to protect the charge generation layer 4, a covering layer 7 is added.
It is common to provide
このように、積層型感光体として二種類の層構成をとる
理由としては、第2図の層構成の感光体を正帯電で用い
ようとしても、これに適合する電荷輸送物質は現在まだ
見つかっていないためである。現段階では、積層型感光
体で正帯電方式を適用する場合には、第3図に示した層
構成の感光体とすることが必要なのである。The reason why the laminated photoreceptor has two types of layer configurations is that even if a photoreceptor with the layer configuration shown in Figure 2 is used for positive charging, a compatible charge transport material has not yet been found. This is because there is no At present, when applying a positive charging method to a laminated type photoreceptor, it is necessary to use a photoreceptor having the layer structure shown in FIG.
第1図の感光体は、電荷発生物質を電荷輸送物質および
樹脂バインダーを溶解した溶液中に分散させ、この分散
液を導電性基体上に塗布することによって作製できる。The photoreceptor shown in FIG. 1 can be produced by dispersing a charge generating material in a solution containing a charge transporting material and a resin binder, and applying this dispersion onto a conductive substrate.
第2図の感光体は、導電性基体上に電荷発生物πの粒子
を溶剤または樹脂バインダー中に分散してソた分散液を
塗布、乾燥し、その上に電荷輸送物質および樹脂バイン
ダーを溶解した溶液を塗布、乾燥することにより作製で
きる。The photoreceptor shown in Figure 2 is produced by dispersing particles of the charge generating material π in a solvent or resin binder, applying a dispersion liquid on the conductive substrate, drying it, and then dissolving the charge transport material and the resin binder on top of the dispersion. It can be produced by applying a solution and drying it.
第3図の感光体は、電荷輸送物質および樹脂バインダー
を溶解した溶液を導電性基体上に塗布、乾燥し、その上
に電荷発生物質の粒子を溶剤または樹脂バインダー中に
分散して得た分散液を塗布、乾燥し、さらに被覆層7を
形成することにより作製できる。The photoreceptor shown in Figure 3 is a dispersion obtained by coating a solution containing a charge transporting substance and a resin binder on a conductive substrate and drying it, and then dispersing particles of a charge generating substance thereon in a solvent or a resin binder. It can be produced by applying a liquid, drying it, and further forming a covering layer 7.
導電性基体lは感光体の電極としての役目と同時に他の
各層の支持体となっており、円筒状、板状、フィルム状
のいずれでも良く、材質的にはアルミニウム、ステンレ
ス鋼、ニッケルナトの金属、あるいはガラス、樹脂など
の上に導電処理をほどこしたものでも良い。The conductive substrate l functions as an electrode for the photoreceptor and at the same time serves as a support for the other layers, and may be cylindrical, plate-shaped, or film-shaped, and may be made of metal such as aluminum, stainless steel, or nickel. Alternatively, it may be made of glass, resin, or the like and subjected to conductive treatment.
電荷発生層4は、前記一般式(I)で示されるアゾ化合
物であられされる電荷発生物質3の粒子を樹脂バインダ
ー中に分散させた材料を塗布して形成され、光を受容し
て電荷を発生する。また、その電荷発生効率が高いこと
と同時に発生した電荷の電荷輸送層6および被覆層7へ
の注入性が重要で、電場依存性が少なく低電場でも注入
の良いことが望ましい。電荷発生層は電荷発生物質を主
体としてこれに電荷輸送物質などを添加して使用するこ
とも可能である。樹脂バインダーとしては、ポリカーボ
ネート、ポリエステル、ポリアミド。The charge generation layer 4 is formed by applying a material in which particles of the charge generation substance 3 made of the azo compound represented by the general formula (I) are dispersed in a resin binder, and receives light to generate charges. Occur. In addition to the high charge generation efficiency, the ability to inject the generated charges into the charge transport layer 6 and the coating layer 7 is also important, and it is desirable that the charge is less dependent on the electric field and can be easily injected even in a low electric field. The charge generation layer is mainly composed of a charge generation substance, and a charge transport substance or the like may be added thereto. Resin binders include polycarbonate, polyester, and polyamide.
ポリウレタン、エポキシ、シリコン樹脂、メタクリル酸
エステルの重合体および共重合体などを適宜組み合わせ
て使用することが可能である。Polyurethane, epoxy, silicone resin, polymers and copolymers of methacrylic acid esters, etc. can be used in appropriate combinations.
電荷輸送層6は樹脂バインダー中に有機電荷輸送物質と
して、ヒドラゾン化合物、ピラゾリン化合物、スチリル
化合物、トリフェニルアミン化合物、オキサゾール化合
物、オキサジアゾール化合物などを溶解・分散させた材
料を塗布して形成され、暗所では絶縁体層として感光体
の電荷を保持し、光受容時には電荷発生層から注入され
る電荷を輸送する機能を発揮する。樹脂バインダーとし
ては、ポリカーボネート、ポリエステル、ポリアミド、
ポリウレタン、エポキシ、シリコン樹脂。The charge transport layer 6 is formed by coating a resin binder with a material in which a hydrazone compound, a pyrazoline compound, a styryl compound, a triphenylamine compound, an oxazole compound, an oxadiazole compound, etc. are dissolved and dispersed as an organic charge transport substance. In the dark, it functions as an insulating layer to hold the charge on the photoreceptor, and when receiving light, it functions to transport the charge injected from the charge generation layer. As a resin binder, polycarbonate, polyester, polyamide,
Polyurethane, epoxy, silicone resin.
メタクリル酸エステルの重合体および共重合体などを用
いることができる。Polymers and copolymers of methacrylic acid esters can be used.
被覆層7は暗所ではコロナ放電の電荷を受容して保持す
る機能を打しており、かつ電荷発生層が感応する光を透
過する性能を有し、露光時に光を透過し、電荷発生層に
到達させ、発生した電荷の注入を受けて表面電荷を中和
消滅させることが必要である。被覆材料としては、ポリ
エステル、ポリアミドなどの有機絶縁性皮膜形成材料が
適用できる。また、これら有機材料とガラス樹脂、 S
in□などの無機材料さらには金属、金属酸化物などの
電気抵抗を低減せしめる材料とを混合して用いることも
できる。被覆材料としては有機絶縁性皮膜形成材料に限
定されることはなく5102などの無機材料さらには金
属、金属酸化物などを蒸着、スパッタリングなどの方法
により形成することも可能である。被覆材料は前述の通
り電荷発生物質の光の吸収極大の波長領域においてでき
るだけ透明であることが望ましい。The coating layer 7 has the function of receiving and retaining the charges of corona discharge in a dark place, and has the ability to transmit the light to which the charge generation layer is sensitive, and transmits the light upon exposure, and the charge generation layer It is necessary to neutralize and eliminate the surface charges by injecting the generated charges. As the coating material, organic insulating film-forming materials such as polyester and polyamide can be used. In addition, these organic materials and glass resin, S
It is also possible to use a mixture of inorganic materials such as in□ and materials that reduce electrical resistance such as metals and metal oxides. The coating material is not limited to organic insulating film-forming materials, and may also be formed using inorganic materials such as 5102, metals, metal oxides, etc. by methods such as vapor deposition and sputtering. As mentioned above, it is desirable that the coating material be as transparent as possible in the wavelength region where the charge generating substance absorbs maximum light.
被覆層自体の膜厚は被覆層の配合組成にも依存するが、
繰り返し連続使用したとき残留電位が増大するなどの悪
影響が出ない範囲で任意に設定できる。The thickness of the coating layer itself depends on the composition of the coating layer, but
It can be set arbitrarily within a range that does not cause adverse effects such as an increase in residual potential when used repeatedly and continuously.
以下、この発明の具体的な実施例について説明する。Hereinafter, specific examples of the present invention will be described.
実施例1
前記化合物Nα1で示されるアゾ化合物50重量部を、
ポリエステル樹脂(商品名バイロン200:東洋結髪)
100重量部と1−フェニル−3−(p−ジエチルアミ
ノスチリル)−5−(p−ジエチルアミノフェニル)−
2−ピラゾリン(A S P P) 100重量部とテ
トラヒドロフラン(THF)溶剤とともに3時間混合機
により混練して塗布液を調製し、導電性基体であるアル
ミ蒸着ポリエステルフィルム(A J! −P E T
)上に、ワイヤーバー法にて塗布して、乾燥後の膜厚
が15μmになるように感光層を形成し、第1図に示し
た構成の感光体を作製した。Example 1 50 parts by weight of the azo compound represented by the compound Nα1,
Polyester resin (product name Byron 200: Toyo Hair)
100 parts by weight and 1-phenyl-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)-
A coating solution was prepared by kneading 100 parts by weight of 2-pyrazoline (A S P P) and a tetrahydrofuran (THF) solvent in a mixer for 3 hours, and a coating solution was prepared using an aluminum vapor-deposited polyester film (A J!-P E T
), a photosensitive layer was formed by coating using a wire bar method so that the film thickness after drying would be 15 μm, thereby producing a photoreceptor having the structure shown in FIG. 1.
実施例2
まず、p−ジエチルアミノベンズアルデヒド−ジフェニ
ルヒドラゾン(ABPH)100重量部をテトラヒドロ
フラン(THF)700重量部に溶かした液と、ポリカ
ーボネート樹脂(パンライト上−1250:帝人製)1
00重量部をTHFとジクロロメタンとの1対1混合溶
剤700重量部で溶解した液とを混合してできた塗布液
をアルミ蒸着ポリエステルフィルム基体上にワイヤーバ
ー法にて塗布し、乾燥後の膜厚が15μmになるように
電荷輸送層を形成した。このようにして得られた電荷輸
送層上に、前記化合物No、 lで示されるアゾ化合物
50重量部、ポリエステル樹脂(商品名バイロン200
.東洋結髪)50重量部、PMMA50重量部をTHF
溶剤とともに3時間混合機により混練して塗布液を調製
しワイヤーバー法にて塗布し、乾燥後の膜厚が0.5μ
mこなるように電荷発生層を形成し、第3図に示した構
成に対応する感光体を作製した。ただし、この発明に直
接関与しない被覆層は設けなかった。Example 2 First, a solution prepared by dissolving 100 parts by weight of p-diethylaminobenzaldehyde-diphenylhydrazone (ABPH) in 700 parts by weight of tetrahydrofuran (THF) and polycarbonate resin (Panlite-1250: manufactured by Teijin) 1
A coating solution prepared by dissolving 00 parts by weight in 700 parts by weight of a 1:1 mixed solvent of THF and dichloromethane was applied onto an aluminum vapor-deposited polyester film substrate using a wire bar method, and the film was dried. A charge transport layer was formed to have a thickness of 15 μm. On the charge transport layer thus obtained, 50 parts by weight of the azo compound represented by Compound No. 1 and a polyester resin (trade name: Vylon 200
.. Toyo Keiko) 50 parts by weight, PMMA 50 parts by weight in THF
A coating solution was prepared by kneading with a solvent in a mixer for 3 hours and applied using a wire bar method, resulting in a film thickness of 0.5 μm after drying.
A charge generation layer was formed in a thickness of m, and a photoreceptor corresponding to the structure shown in FIG. 3 was produced. However, a coating layer not directly related to this invention was not provided.
実施例3
実施例2における電荷輸送物質を、ABPHからスチリ
ル化合物であるα−フェニル−4’−N。Example 3 The charge transport substance in Example 2 was changed from ABPH to α-phenyl-4′-N, which is a styryl compound.
N−ジメチルアミノスチルベンに変え、その他は実施例
2と同様にして電荷輸送層を形成し、さらに電荷発生層
を形成し感光体を作製した。A charge transport layer was formed in the same manner as in Example 2 except that N-dimethylaminostilbene was used, and a charge generation layer was further formed to produce a photoreceptor.
実施例4
実施例2における電荷輸送物質を、ABPHからトリフ
ェニルアミン化合物であるトリ (p−)リル)アミン
に変え、その他は実施例2と同様にして電荷輸送層を形
成し、さらに電荷発生層を形成し感光体を作製した。Example 4 A charge transport layer was formed in the same manner as in Example 2 except that the charge transport material in Example 2 was changed from ABPH to tri(p-)lylamine, which is a triphenylamine compound. A layer was formed to produce a photoreceptor.
実施例5
実施例2における電荷輸送物質を、ABPHからオキサ
ジアゾール化合物である〕2)5−ビス(p−ジエチル
アミノフェニル)−1,3,4−オキサジアゾールに変
え、その他は実施例2と同様にして電荷輸送層を形成し
、さらに電荷発生層を形成し感光体を作製した。Example 5 The charge transport substance in Example 2 was changed from ABPH to an oxadiazole compound] 2) 5-bis(p-diethylaminophenyl)-1,3,4-oxadiazole, and the rest was the same as in Example 2. A charge transport layer was formed in the same manner as above, and a charge generation layer was further formed to produce a photoreceptor.
このようにして得られた感光体の電子写真特性を川口電
機製静電記録紙試験装置r S P−428Jを用いて
測定した。その結果を第1表に示す。The electrophotographic properties of the photoreceptor thus obtained were measured using an electrostatic recording paper tester RSP-428J manufactured by Kawaguchi Electric. The results are shown in Table 1.
感光体の表面電位V、(ボルト)は暗所で+6□0kV
のコロナ放電を10秒間行って感光体表面を正帯電させ
たときの初期の表面電位であり、続いてコロナ放電を中
止した状態で2秒間暗所保持したときの表面電位V d
(ボルト)を測定し、さらに続いて感光体表面に照度2
ルツクスの白色光を照射してV、が半分になるまでの時
間(秒)を求め半減衰露光量E17z(ルックス・秒)
とした。また、照度2ルツクスの白色光を10秒間照射
したときの表面電位を残留電位V、(ボルト、)とした
。The surface potential V, (volt) of the photoreceptor is +6□0kV in the dark
This is the initial surface potential when corona discharge is performed for 10 seconds to positively charge the surface of the photoreceptor, and then the surface potential is V d when the corona discharge is stopped and the surface is held in the dark for 2 seconds.
(volts), and then the illuminance 2 on the photoreceptor surface.
Calculate the time (seconds) it takes for V to be halved after irradiating lux white light, and calculate the half-attenuation exposure amount E17z (lux seconds)
And so. Further, the surface potential when white light with an illuminance of 2 lux was irradiated for 10 seconds was defined as the residual potential V, (volts).
、1ず
第 1
表
第1表に見られるように、実施例1ないし5の感光体は
、表面電位vs、半減衰露光BEl/2.残留電位V、
ともに良好であった。, 1 Table 1 As seen in Table 1, the photoreceptors of Examples 1 to 5 had surface potential vs. half-attenuation exposure BEI/2. residual potential V,
Both were good.
実施例6
前記化合物Nα2からNα35で示されるアゾ化合物1
00重量部をそれぞれポリエステル樹脂(商品名バイロ
ン200;東洋結髪)100重量部とTHF溶剤ととも
に3時間混合機により混練して塗布液を調製し、アルミ
ニウム支持体上に約0.5μmになるように塗布し電荷
発生層をそれぞれ形成した。この上に1.実施例2にお
ける電荷輸送物質をABPHからASPPに変え、その
他は実施例2と同様にして得られた電荷輸送層用の塗布
液を約15μmになるように塗布し電荷輸送層を形成し
て、第2図に示した構成の感光体を作製した。Example 6 Azo compound 1 represented by the above compounds Nα2 to Nα35
A coating solution was prepared by kneading 100 parts by weight of each of 00 parts by weight of a polyester resin (trade name: Byron 200; Toyo Keiko) and a THF solvent for 3 hours in a mixer, and coated on an aluminum support to a thickness of about 0.5 μm. A charge generation layer was formed by applying the coating. On top of this 1. The charge transport material in Example 2 was changed from ABPH to ASPP, and the coating liquid for a charge transport layer obtained in the same manner as in Example 2 was applied to a thickness of about 15 μm to form a charge transport layer. A photoreceptor having the configuration shown in FIG. 2 was produced.
このようにして得られた感光体の電子写真特性を、川口
電機製静電記録紙試験装置r S P−428Jを用い
、帯電極性を正帯電から負帯電に変更した以外は実施例
1と同様にして測定した。この結果を第2表に示す。The electrophotographic properties of the photoreceptor thus obtained were evaluated in the same manner as in Example 1, except that the electrostatic recording paper tester RSP-428J manufactured by Kawaguchi Electric was used, and the charging polarity was changed from positive charging to negative charging. It was measured as follows. The results are shown in Table 2.
第 2
表(その2)
第
表
(その3)
さらに、必要に応じて表面に被覆層を設置して、耐久性
を向上させることが可能である。Table 2 (Part 2) Table (Part 3) Furthermore, if necessary, a coating layer can be provided on the surface to improve durability.
第1図、第2図および第3図はこの発明の感光体のそれ
ぞれ異なる実施例を示す概念的断面図である。
1 導電性基体、2 a、 2 b、 2 C感光
層、3 電荷発生物質、4 電荷発生層、5 電荷輸送
物質、6〜電荷輸送層、7 被覆層。
第2表に見られるように、前記アゾ化合物隠2〜N(L
35を用いた感光体についても、半減衰露光量E +/
21 残留電位vrともに良好であった。
〔発明の効果〕
この発明によれば、導電性基体上に形成する感光層に電
荷発生物質として前記一般式(I)で示されるアゾ化合
物を用いることとしたため、正帯電および負帯電におい
ても高感度でしかも繰り返し特性の優れた感光体を得る
ことができる。FIGS. 1, 2, and 3 are conceptual cross-sectional views showing different embodiments of the photoreceptor of the present invention. Reference Signs List 1 conductive substrate, 2 a, 2 b, 2 C photosensitive layer, 3 charge generating material, 4 charge generating layer, 5 charge transporting material, 6 - charge transporting layer, 7 coating layer. As seen in Table 2, the azo compound hidden 2~N(L
Also for the photoreceptor using 35, the half-attenuation exposure amount E +/
21 Both residual potential vr were good. [Effects of the Invention] According to the present invention, since the azo compound represented by the general formula (I) is used as a charge generating substance in the photosensitive layer formed on the conductive substrate, the azo compound represented by the general formula (I) is highly charged even in positive and negative charging. A photoreceptor with excellent sensitivity and repeatability can be obtained.
Claims (1)
とも一種類を含む感光層を備えた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▼ 〔式( I )中、Ar_1およびAr_2は以下のそれ
ぞれ置換されていてもよい芳香族炭化水素基、芳香族複
素環基のうちのいずれかを表し(ただし、同時に置換も
しくは未置換のフェニレン基になることはない)、Cp
はカップラー残基を表す。〕 2)特許請求の範囲第1項記載の感光体において、前記
一般式( I )のCp(カップラー残基)が下記の一般
式(II)ないし(V)で示されるもののうちのいずれか
であ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▼−−−−−−−−−
(II)▲数式、化学式、表等があります▼−−−−−(
III)▲数式、化学式、表等があります▼−−−−−(
IV)▲数式、化学式、表等があります▼−−−−−(V
)〔式(II)ないし(V)において、Zはベンゼン環と
縮合して多環芳香環あるいは複素環を形成する残基を表
し、X_1はOR_1もしくはNR_2R_3(R_1
、R_2およびR_3は水素原子、または以下のそれぞ
れ置換されていてもよいアルキル基、アリール基、芳香
族複素環基のうちのいずれかを表す)を表し、X_2お
よびX_5は以下のそれぞれ置換されていてもよいアル
キル基、アリール基、芳香族複素環基のうちのいずれか
を表し、X_3およびX_6は水素原子、シアノ基、カ
ルバモイル基、カルボキシル基、エステル基、アシル基
のうちのいずれかを表し、X_4は水素原子、または以
下のそれぞれ置換されていてもよいアルキル基、シクロ
アルキル基、アルケニル基、アリール基、芳香族複素環
基のうちのいずれかを表し、X_7およびX_8は水素
原子、ハロゲン原子、ニトロ基、または以下のそれぞれ
置換されていてもよいアルキル基、アルコキシ基のうち
のいずれかを表し、X_9はアルキル基、アリール基、
カルボキシル基、エステル基のうちのいずれかを表し、
X_1_0はそれぞれ置換されていてもよいアリール基
、芳香族複素環基のうちのいずれかを表す。〕[Scope of Claims] 1) An electrophotographic photoreceptor comprising a photosensitive layer containing at least one compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In formula (I), Ar_1 and Ar_2 each represent one of the following optionally substituted aromatic hydrocarbon groups and aromatic heterocyclic groups (however, , cannot be a substituted or unsubstituted phenylene group at the same time), Cp
represents a coupler residue. 2) In the photoreceptor according to claim 1, Cp (coupler residue) in the general formula (I) is one of the following general formulas (II) to (V). A photoreceptor for electrophotography characterized by the following. ▲There are mathematical formulas, chemical formulas, tables, etc.▼−−−−−−−−−
(II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼−−−−−(
III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼−−−−−(
IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼------(V
) [In formulas (II) to (V), Z represents a residue condensed with a benzene ring to form a polycyclic aromatic ring or a heterocycle, and X_1 is OR_1 or NR_2R_3(R_1
, R_2 and R_3 represent a hydrogen atom, or each of the following optionally substituted alkyl groups, aryl groups, and aromatic heterocyclic groups), and X_2 and X_5 each represent the following substituted X_3 and X_6 represent any one of a hydrogen atom, a cyano group, a carbamoyl group, a carboxyl group, an ester group, and an acyl group. , X_4 represents a hydrogen atom, or any of the following optionally substituted alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, and aromatic heterocyclic groups, and X_7 and X_8 represent hydrogen atoms, halogen represents an atom, a nitro group, or any of the following optionally substituted alkyl groups and alkoxy groups, and X_9 is an alkyl group, an aryl group,
Represents either a carboxyl group or an ester group,
X_1_0 each represents either an optionally substituted aryl group or an aromatic heterocyclic group. ]
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16301988A JPH0212257A (en) | 1988-06-30 | 1988-06-30 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16301988A JPH0212257A (en) | 1988-06-30 | 1988-06-30 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0212257A true JPH0212257A (en) | 1990-01-17 |
Family
ID=15765648
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16301988A Pending JPH0212257A (en) | 1988-06-30 | 1988-06-30 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0212257A (en) |
-
1988
- 1988-06-30 JP JP16301988A patent/JPH0212257A/en active Pending
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