JPH0515263B2 - - Google Patents
Info
- Publication number
- JPH0515263B2 JPH0515263B2 JP13817386A JP13817386A JPH0515263B2 JP H0515263 B2 JPH0515263 B2 JP H0515263B2 JP 13817386 A JP13817386 A JP 13817386A JP 13817386 A JP13817386 A JP 13817386A JP H0515263 B2 JPH0515263 B2 JP H0515263B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- formula
- heterocyclic
- 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 - Lifetime
Links
- -1 bisazo compound Chemical class 0.000 claims description 23
- 108091008695 photoreceptors Proteins 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 25
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 3
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- 239000012790 adhesive layer Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical compound NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- CFOCDGUVLGBOTL-UHFFFAOYSA-N 2-[2-[4-(diethylamino)phenyl]ethenyl]-n,n-diethyl-1,3-benzoxazol-6-amine Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=NC2=CC=C(N(CC)CC)C=C2O1 CFOCDGUVLGBOTL-UHFFFAOYSA-N 0.000 description 1
- WGRSVHBSCVGKDP-UHFFFAOYSA-N 2-ethyl-9h-carbazole-1-carbaldehyde Chemical compound C1=CC=C2C3=CC=C(CC)C(C=O)=C3NC2=C1 WGRSVHBSCVGKDP-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
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- BLPSRWHAQDYHTQ-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3,5,6-tetrakis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1C(C(=C1C=2C=CC(N)=CC=2)C=2C=CC(C)=CC=2)=C(N)C(C=2C=CC(C)=CC=2)=C1C1=CC=C(C)C=C1 BLPSRWHAQDYHTQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BLZBFDSZGUSPEJ-UHFFFAOYSA-N 4-[2-[3-[4-(diethylamino)phenyl]-3-[2-[4-(diethylamino)phenyl]ethenyl]-2-phenyl-1h-pyrazol-5-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC(NN1C=2C=CC=CC=2)=CC1(C=1C=CC(=CC=1)N(CC)CC)C=CC1=CC=C(N(CC)CC)C=C1 BLZBFDSZGUSPEJ-UHFFFAOYSA-N 0.000 description 1
- MWCJVXVYZMXSEE-UHFFFAOYSA-N 4-[5-[4-(diethylamino)-2-methylphenyl]-1,3,4-oxadiazol-2-yl]-n,n-diethyl-3-methylaniline Chemical class CC1=CC(N(CC)CC)=CC=C1C1=NN=C(C=2C(=CC(=CC=2)N(CC)CC)C)O1 MWCJVXVYZMXSEE-UHFFFAOYSA-N 0.000 description 1
- UZGVMZRBRRYLIP-UHFFFAOYSA-N 4-[5-[4-(diethylamino)phenyl]-1,3,4-oxadiazol-2-yl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(CC)CC)O1 UZGVMZRBRRYLIP-UHFFFAOYSA-N 0.000 description 1
- XXWVEJFXXLLAIB-UHFFFAOYSA-N 4-[[4-(diethylamino)-2-methylphenyl]-phenylmethyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=CC=C1 XXWVEJFXXLLAIB-UHFFFAOYSA-N 0.000 description 1
- QAVGSORLCPBANE-UHFFFAOYSA-N 4-[[bis(4-methoxyphenyl)hydrazinylidene]methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 QAVGSORLCPBANE-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920004142 LEXAN™ Polymers 0.000 description 1
- 239000004418 Lexan Substances 0.000 description 1
- 239000004793 Polystyrene Substances 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
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- CVKIMZDUDFGOLC-UHFFFAOYSA-N n,n-diphenyl-2-(2-phenylethenyl)aniline Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 CVKIMZDUDFGOLC-UHFFFAOYSA-N 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
Description
産業上の利用分野
本発明は、電子写真感光体に関し、詳しくは、
特定のアゾ顔料を含む感光層を有する電子写真感
光体に関する。
従来の技術
従来、電子写真感光材料として、無定形セレ
ン、セレン合金、硫化カドミウム、酸化亜鉛など
の無機系の光導電性物質やポリビニルカルバゾー
ル及びポリビニルカルバゾール誘導体に代表され
る有機系の光導電性物質が広く知られている。
有機系光導電性物質は、無機系のものに比し、
透明性、皮膜形成性、可撓性、製造性などの点で
優れているという利点がある。
発明が解決しようとする問題点
この様な多くの利点を有しながら有機系の光導
電性物質が電子写真感光体に用いられなかつたの
は、感度及び耐久性の点で無機系のものに劣るた
めであつた。
したがつて、本発明は、有機系の光導電性物質
を用いた場合における上記の欠点に鑑みなされた
ものであつて、その目的は、高感度で高耐久性の
電子写真感光体を提供するにある。
問題点を解決するための手段
本発明の電子写真感光体は、導電性支持体上の
感光層に下記一般式（）で表わされるビスアゾ
化合物を含有することを特徴とする。
［式中、Ａは二価の芳香族炭化水素基又は窒素原
子を環内に含む二価の複素環基を示し、Ｘは水素
原子又は塩素原子を示し、Cpは
INDUSTRIAL APPLICATION FIELD The present invention relates to an electrophotographic photoreceptor, and more specifically,
The present invention relates to an electrophotographic photoreceptor having a photosensitive layer containing a specific azo pigment. Conventional technology Conventionally, inorganic photoconductive substances such as amorphous selenium, selenium alloys, cadmium sulfide, and zinc oxide, and organic photoconductive substances such as polyvinyl carbazole and polyvinyl carbazole derivatives have been used as electrophotographic photosensitive materials. is widely known. Compared to inorganic photoconductive materials, organic photoconductive materials are
It has the advantage of being excellent in terms of transparency, film-forming properties, flexibility, manufacturability, etc. Problems to be Solved by the Invention Despite having such many advantages, organic photoconductive materials have not been used in electrophotographic photoreceptors because inorganic photoconductors have poor sensitivity and durability. It was to be inferior. Therefore, the present invention was made in view of the above-mentioned drawbacks when using an organic photoconductive substance, and its purpose is to provide an electrophotographic photoreceptor with high sensitivity and high durability. It is in. Means for Solving the Problems The electrophotographic photoreceptor of the present invention is characterized in that the photosensitive layer on the conductive support contains a bisazo compound represented by the following general formula (). [In the formula, A represents a divalent aromatic hydrocarbon group or a divalent heterocyclic group containing a nitrogen atom in the ring, X represents a hydrogen atom or a chlorine atom, and Cp represents
【式】【formula】
【式】 及び【formula】 as well as
【式】
の中から選ばれる基を示す。（ここで、Ｙは置換
又は未置換の炭素環式芳香族環、又は置換又は未
置換の複素環式芳香族環を構成するに必要な原子
段を示し、Ｚは置換又は未置換のカルバモイル
基、置換又は未置換のスルフアモイル基、又は置
換又は未置換の複素５員環基を示し、R1は水素
原子、置換又は未置換のアルキル基、置換又は未
置換のアミノ、置換又は未置換のカルバモイル
基、置換又は未置換のスルフアモイル基カルボキ
シル基又はそのエステル基を示し、R2は置換又
は未置換のアリール基、又は置換又は未置換のア
ルキル基を示し、R3は置換又は未置換のアリー
ル基、置換又は未置換のアルキル基、又は置換又
は未置換の複素環基を示す。）］
以下、本発明を詳細に説明する。
本発明の電子写真感光体において使用する前記
一般式（）で表わされるビスアゾ化合物につい
てさらに説明すると、一般式（）において、Ａ
は二価の芳香族炭化水素基又は窒素原子を環内に
含む二価の複素環基を示すが、二価の芳香族炭化
水素基としては、例えば、ｏ−フエニレン基等の
二価の単環式芳香族炭化水素基、ｏ−ナフチレン
基、ペリナフチレン基、１，２−アントラキノニ
ル基、９，10−フエナントリレン基等の二価の縮
合多環式芳香族炭化水素基があげられる。また、
窒素原子を環内に有する二価の複素環基として
は、３，４−ピラゾールジイル基、２，３−ピリ
ジンジイル基、３，４−ピリジジイル基、４，５
−ピリミジンジイル基、５，６−ベンズイミダゾ
ールジイル基、６，７−キノリンジイル基等の複
素環基が挙げられる。
感度及び耐久性を考慮した場合、Ａはｏ−フエ
ニレン基、ｏ−ナフチレン基、ペリナフチレン
基、２，３−ピリジンジイル基、３，４−ピリジ
ンジイル基、４，５−ピリジンジイル基、９，10
−フエナントリレン基を表わすのが好ましく、特
にｏ−フエニレン基又はｏ−ナフチレン基を表わ
すのが好ましい。
上記の二価の芳香族炭化水素基及び窒素原子を
環内に含む二価の複素環基は置換基を有してもよ
い。置換基としては、C1〜C18のアルキル基、C1
〜C4のアルコキシ基、C1〜C4のアルコキシルカ
ルボニル基、カルボキシル基、ヒドロキシ基、ニ
トロ基、シアノ基、ハロゲン原子、トリフロロメ
チル基、カルバモイル基、スルフアモイル基、フ
エノキシ基等挙がげられる。中でも、アルキル
基、アルコキシ基、カルボキシル基、ヒドロキシ
基、ニトロ基、ハロゲン原子、特に、メチル基、
メトキシ基、ニトロ基、塩素原子、カルボキシル
基が好ましい。
一般式（）において、Ｘは水素原子又は塩素
原子を示す。
また、一般式（）において、Cpは、[Formula] Indicates a group selected from the following. (Here, Y represents the atomic stage necessary to constitute a substituted or unsubstituted carbocyclic aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring, and Z represents a substituted or unsubstituted carbamoyl group. , a substituted or unsubstituted sulfamoyl group, or a substituted or unsubstituted 5-membered heterocyclic group, R 1 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino, a substituted or unsubstituted carbamoyl R2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group, and R3 represents a substituted or unsubstituted aryl group. , a substituted or unsubstituted alkyl group, or a substituted or unsubstituted heterocyclic group)] The present invention will be described in detail below. To further explain the bisazo compound represented by the general formula () used in the electrophotographic photoreceptor of the present invention, in the general formula (), A
indicates a divalent aromatic hydrocarbon group or a divalent heterocyclic group containing a nitrogen atom in the ring, but as a divalent aromatic hydrocarbon group, for example, a divalent monomer such as an o-phenylene group Examples include divalent condensed polycyclic aromatic hydrocarbon groups such as a cyclic aromatic hydrocarbon group, an o-naphthylene group, a perinaphthylene group, a 1,2-anthraquinonyl group, and a 9,10-phenanthrylene group. Also,
Examples of the divalent heterocyclic group having a nitrogen atom in the ring include 3,4-pyrazolediyl group, 2,3-pyridinediyl group, 3,4-pyrididiyl group, 4,5
Examples include heterocyclic groups such as -pyrimidinediyl group, 5,6-benzimidazolediyl group, and 6,7-quinolinediyl group. When considering sensitivity and durability, A is o-phenylene group, o-naphthylene group, perinaphthylene group, 2,3-pyridinediyl group, 3,4-pyridinediyl group, 4,5-pyridinediyl group, 9, Ten
-phenanthrylene group is preferred, and o-phenylene group or o-naphthylene group is particularly preferred. The divalent aromatic hydrocarbon group and the divalent heterocyclic group containing a nitrogen atom in the ring may have a substituent. As a substituent, a C 1 to C 18 alkyl group, a C 1
~ C4 alkoxy group, C1 to C4 alkoxylcarbonyl group, carboxyl group, hydroxy group, nitro group, cyano group, halogen atom, trifluoromethyl group, carbamoyl group, sulfamoyl group, phenoxy group, etc. . Among them, alkyl groups, alkoxy groups, carboxyl groups, hydroxy groups, nitro groups, halogen atoms, especially methyl groups,
Preferred are methoxy group, nitro group, chlorine atom, and carboxyl group. In the general formula (), X represents a hydrogen atom or a chlorine atom. Also, in the general formula (), Cp is
【式】【formula】
【式】 及び【formula】 as well as
【式】 から選ばれる基を表わすが、特に好ましいものは【formula】 represents a group selected from, but particularly preferred ones are
【式】又は[Formula] or
【式】
である。
上記基において、Ｙは、置換又は未置換の炭素
環式芳香族環又は置換又は未置換の複素環式芳香
族環を構成するに必要な原子団を表わすが、特に
好ましいのは、ベンゼン環、ナフタレ環、カルバ
ゾール環、ベンゾフラン環、インドール環等の芳
香族環を形成するものである。
また、Ｚは、置換又は未置換のカルバモイル
基、置換又は未置換のスルフアモイル基、又は置
換又は未置換の複素五員環を形成するに必要な原
子団を示すが、中でもアリール置換カルバモイル
基、ベンズイミダゾリル基が好ましい。
また、R1は水素原子、置換又は未置換のアル
キル基、置換又は未置換のアミノ基、置換又は未
置換のカルバモイル基、置換又は未置換のスルフ
アモイル基、カルボキシル基又はそのエステル基
を示すが、中でもC1〜C4のアルキル基、カルボ
キシル基、C1〜C4のアルコキシカルボニル基が
好ましい。
R2は置換又は未置換のアリール基、又は置換
又は未置換のアルキル基を示すが置換又は未置換
のフエニル基を示すのが特に好ましい。
R3は置換又は未置換のアリール基、置換又は
未置換のアルキル基、又は置換又は未置換の複素
環基を示すが、置換又は未置換のフエニル基、
C1〜C4のアルキル基、又は置換又は未置換のベ
ンズイミダゾリル基を示すのが特い好ましい。
本発明において使用する上記ビスアゾ化合物の
具体的なものとしては次のものがあげられる。し
かしながら、本発明におけるビスアゾ化合物がこ
れ等のものに限定されるものではない。
[Formula] is. In the above group, Y represents an atomic group necessary to constitute a substituted or unsubstituted carbocyclic aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring, and particularly preferred are a benzene ring, It forms aromatic rings such as naphthalene rings, carbazole rings, benzofuran rings, and indole rings. In addition, Z represents a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted sulfamoyl group, or an atomic group necessary to form a substituted or unsubstituted five-membered heterocyclic ring, and among them, an aryl-substituted carbamoyl group, a benzene An imidazolyl group is preferred. In addition, R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted sulfamoyl group, a carboxyl group or an ester group thereof, Among these, C1 - C4 alkyl groups, carboxyl groups, and C1 - C4 alkoxycarbonyl groups are preferred. R 2 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted alkyl group, and preferably represents a substituted or unsubstituted phenyl group. R 3 represents a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted heterocyclic group, and a substituted or unsubstituted phenyl group,
Particular preference is given to a C1 - C4 alkyl group or a substituted or unsubstituted benzimidazolyl group. Specific examples of the above-mentioned bisazo compounds used in the present invention include the following. However, the bisazo compound in the present invention is not limited to these compounds.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
本発明において用いる上記ジスアゾ化合物は、
例えば、相当するジアミンを常法によりテトラゾ
化し、一般式Ｈ−Cpで示されるカツプラーとア
ルカリの存在下でカツプリングするか、あるい
は、相当するジアミンのテトラゾニウム塩を硼弗
化塩又は塩化亜鉛複塩の形で単離した後、適当な
溶媒（例えば、Ｎ，Ｎ−ジメチルフオルムアミ
ド、ヂメチルスルホキシド等）中でアルカリの存
在下、上記カツプラーとカツプリングすることに
よつて合成することができる。
本発明において、上記ビスアゾ化合物は、導電
性支持体に設けられた感光層中に含有させるが、
感光層は単層構造のものでも、また電荷発生層と
電荷輸送層とに機能分離された積層構造のもので
もよい。
本発明の電子写真感光体は、例えば(1)導電性支
持体上に、ビスアゾ化合物を、電荷輸送物質を含
む結着樹脂中に分散させてなる感光層を設けたも
の、(2)導電性支持体上に、ビスアゾ化合物及び電
荷移動錯体を結着樹脂中に分散させてなる感光層
を設けたもの、及び(3)導電性支持体上に、ビスア
ゾ化合物を含む電荷発生層及び電荷輸送物質を含
む電荷輸送層を設けたものに大別することができ
る。
本発明の電子写真感光平における導電性支持体
としては、アルミニウム、ニツケル、クロム、ス
テンレススチール等からなる金属板、金属ドラ
ム、又は金属箔及び金属その他の導電性物質の薄
膜を設けたプラスチツクフイルム、導電性付与剤
を塗布又は含浸させた紙又はプラスチツクフイル
ム等が用いられる。
本発明において、導電性支持体上に形成する感
光層において、上記ビスアゾ化合物を結着樹脂中
に分散させる場合には、ビスアゾ化合物は、3μ
以下、好ましくは0.3μ以下の粒径の微粒子として
分散させ、そしてその配合量は、感光層に対して
20重量％ないし90重量％とするが望ましい。
結着樹脂としては、ポリスチレン、シリコーン
樹脂、ポリカーボネート、アクリル樹脂、メタク
リル樹脂、ポリエステル、ビニル系重合体、例え
ば、ポリビニルブチラール等、セルロース類、例
えば、セルロースエステル、セルロースエーテル
等、アルキツド樹脂等が使用できる。
本発明の電子写真感光体において使用される電
荷輸送物質としては、例えば、Ｎ−メチル−Ｎ−
フエニルヒドラジノ−３−メチリデン−９−エチ
ルカルバゾール、Ｎ，Ｎ−ジフエニルヒドラジノ
−３−メチリデン−９−エチルカルバゾール、
Ｎ，Ｎ−ジフエニルヒドラジノ−３−メチリデン
−９−メチルカルバゾール、ｐ−ジエチルアミノ
ベンズアルデヒド−Ｎ，Ｎ−ジフエニルヒドラゾ
ン、ｐ−ジエチルアミノベンズアルデヒド−Ｎ，
Ｎ−ジ（ｐ−メトキシフエニル）ヒドラゾン、ｐ
−ジエチルアミノベンズアルデヒド−Ｎ（α−ナ
フチル）−Ｎ−フエニルヒドラゾン、β，β−ジ
（４−メトキシフエニル）アクロレインジフエニ
ルヒドラゾン等のヒドラゾン類、１−フエニル−
３（ｐ−ジエチルアミノスチリル）−５−（ｐ−ジ
エチルアミノスチリル）−５−（ｐ−ジエチルアミ
ノフエニル）ピラゾリン、１−［キノリル(2)］−３
−（ｐ−ジエチルアミノスチリル）−５−（ｐ−ジ
エチルアミノフエニル）ピラゾリン等のピラゾリ
ン類、２−（ｐ−ジプロピルアミノフエニル）−４
−（ｐ−ジメチルアミノフエニル）−５−（２−ク
ロロフエニル）オキサゾール、２−（ｐ−ジエチ
ルアミノスチリル）−６−ジエチルアミノベンズ
オキサゾール等のオキサゾール系化合物、２，５
−ビス（ｐ−ジエチルアミノフエニル）−１，３，
４−オキサジアゾール、２，５−ビス（4′−ジエ
チルアミノ−2′−メチルフエニル）−１，３，４
−オキサジアゾール等のオキサジアゾール系化合
物、ビス（４−ジエチルアミノ−２−メチルフエ
ニル）−フエニルメタン等のトリアリ−ルメタン
系化合物、トリフエニルアミン、２，4′，4″−ト
リメチルトリフエニルアミン、１，１−ビス
［4′−Ｎ，Ｎ−ジ（ｐ−メチルフエニル）アミノ
フエニル］シクロヘキサン等のトリアリ−ルアミ
ン系化合物、５−（ｐ−ジエチルアミノスチリル
アントラセン等のアントラセン系化合物、α−フ
エニル−4′−Ｎ，Ｎ−ジフエニルアミノスチルベ
ン、4′−Ｎ，Ｎ−ジ（ｐ−メトキシフエニル）ア
ミノスチルベン等のスチルベン系化合物、Ｎ，
N′−ジフエニル−Ｎ，N′−ビス（３−メチルフ
エニル）−［１，1′−ビフエニル］−４，4′−ジア
ミン、３，3′−ジメチル−Ｎ，Ｎ，N′，N′−テ
トラキス（４−メチルフエニル）−［１，1′−ビフ
エニル］−４，4′−ジアミン等のベンジジン系化
合物等があげられ、これ等は結着樹脂中に含有さ
せる。さらにまた、ポリ−Ｎ−ビニルカルバゾー
ル、ハロゲン化ポリ−Ｎ−ビニルカルバゾール、
ポリビニルアントラセン、ポリ−９−ビニルフエ
ニルアントラセン、ポリビニルピレン、ポリビニ
ルアクリジン、ポリビニルアセナフチレン、ポリ
グリシジルカルバゾール、ピレン−ホルムアルデ
ヒド樹脂、エチルカルバゾール−ホルムアルデヒ
ド樹脂等の光導電性ポリマーがあげられ、これ等
はそれ自体で層を形成してもよい。
本発明において、感光層が積層構造の場合に
は、電子写真感光体の感度が高く、残留電位が低
いので好ましい。この場合、電荷発生層は、上記
のようにビスアゾ化合物を、結着樹脂中に分散さ
せて形成してもよいが、ビスアゾ化合物の昇華又
は蒸着によつて形成してもよい。また、電荷発生
層あるいは電荷輸送層のどちらを上層に設けても
よく、電荷発生層を上層に設けた場合には電子写
真感光体は、正帯電型として、電荷輸送層を上層
に設けた場合には、負帯電型として用いることが
できる。
本発明の電子写真感光体において上記の感光層
と導電性支持体の間には接着層を設けてもよい。
接着層は、通常用いられている、例えば、ポリエ
ステル等の合成樹脂によつて構成され、通常、膜
厚0.5〜5μ程度に形成される。
実施例
以下、本発明を実施例によつて説明する。
実施例 １
ポリビニルブチラール樹脂（商品名：BLX積
水化学(株)）１重量部をシクロヘキサノン40重量部
に溶解し、その中に例示化合物NO.1を３重量部
混合し、次いでペイントシエーカーにてよく分散
し、これをアプリケーターにてアルミニウムシー
ト上に塗布し、乾燥して、電荷発生層を形成し
た。乾燥後の膜厚は0.2μｍであつた。
形成された電荷発生層上にＮ，N′−ジフエニ
ル−Ｎ，N′−ビス（３−メチルフエニル）−［１，
1′−ビフエニル］−４，4′−ジアミン１重量部、
ポリカーボネート樹脂（商品名：レキサン145、
GE社製、分子量35.000〜40.000）１重量部、ジク
ロルメタン15重量部からなる均一溶液をアプリケ
ーターで塗布し、乾燥して電荷輸送層を形成し
た。膜厚は20μｍであつた。
このようにして得られた電子写真感光体を、静
電複写紙試験装置（川口電機製作所製SP−428）
を用いて、以下の特性評価を行つた。まず、−
6KVのコロナ帯電を施して、負帯電させた後、
２秒間暗所に放置し、その時の表面電位Vpo
（volt）を測定し、次いで、タングステンランプ
を用いて表面の照度が５ルツクスになるようにし
て光を照射し、その表面電位がVpoの1/2になる
までの時間を求め、露光量Ｅ1/2（lux・sec）を
算出した。
さらに同様の測定を20回繰り返して行つた。
結果は、第１表に示す通りである。[Table] The above disazo compounds used in the present invention are:
For example, the corresponding diamine is tetrazotized by a conventional method and coupled with a coupler represented by the general formula H-Cp in the presence of an alkali, or the tetrazonium salt of the corresponding diamine is converted into a borofluoride salt or a zinc chloride double salt. It can be synthesized by isolating the compound as a form and then coupling it with the above coupler in a suitable solvent (eg, N,N-dimethylformamide, dimethyl sulfoxide, etc.) in the presence of an alkali. In the present invention, the bisazo compound is contained in the photosensitive layer provided on the conductive support,
The photosensitive layer may have a single layer structure or a laminated structure in which a charge generation layer and a charge transport layer are functionally separated. The electrophotographic photoreceptor of the present invention includes, for example, (1) a photosensitive layer formed by dispersing a bisazo compound in a binder resin containing a charge transport substance on a conductive support; (2) a conductive support; A photosensitive layer comprising a bisazo compound and a charge transfer complex dispersed in a binder resin is provided on a support, and (3) a charge generation layer containing a bisazo compound and a charge transport substance are provided on a conductive support. It can be roughly divided into those provided with a charge transport layer containing. The conductive support in the electrophotographic photosensitive plate of the present invention may be a metal plate made of aluminum, nickel, chromium, stainless steel, etc., a metal drum, or a plastic film provided with a metal foil and a thin film of metal or other conductive substance. Paper or plastic film coated with or impregnated with a conductivity imparting agent is used. In the present invention, when the bisazo compound is dispersed in the binder resin in the photosensitive layer formed on the conductive support, the bisazo compound is
Hereinafter, it is preferably dispersed as fine particles with a particle size of 0.3 μ or less, and the amount of blending is determined relative to the photosensitive layer.
It is desirable that the content be 20% to 90% by weight. As the binder resin, polystyrene, silicone resin, polycarbonate, acrylic resin, methacrylic resin, polyester, vinyl polymer such as polyvinyl butyral, cellulose such as cellulose ester, cellulose ether, alkyd resin, etc. can be used. . As the charge transport material used in the electrophotographic photoreceptor of the present invention, for example, N-methyl-N-
Phenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole,
N,N-diphenylhydrazino-3-methylidene-9-methylcarbazole, p-diethylaminobenzaldehyde-N,N-diphenylhydrazone, p-diethylaminobenzaldehyde-N,
N-di(p-methoxyphenyl)hydrazone, p
-Diethylaminobenzaldehyde-N(α-naphthyl)-N-phenylhydrazone, hydrazones such as β,β-di(4-methoxyphenyl)acrolein diphenylhydrazone, 1-phenyl-
3(p-diethylaminostyryl)-5-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[quinolyl(2)]-3
Pyrazolines such as -(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 2-(p-dipropylaminophenyl)-4
-Oxazole compounds such as -(p-dimethylaminophenyl)-5-(2-chlorophenyl)oxazole, 2-(p-diethylaminostyryl)-6-diethylaminobenzoxazole, 2,5
-bis(p-diethylaminophenyl)-1,3,
4-Oxadiazole, 2,5-bis(4'-diethylamino-2'-methylphenyl)-1,3,4
-Oxadiazole compounds such as oxadiazole, triarylmethane compounds such as bis(4-diethylamino-2-methylphenyl)-phenylmethane, triphenylamine, 2,4′,4″-trimethyltriphenylamine, 1 , 1-bis[4'-N,N-di(p-methylphenyl)aminophenyl]cyclohexane and other triarylamine compounds, 5-(p-diethylaminostyryl anthracene and other anthracene compounds, α-phenyl-4'- Stilbene compounds such as N,N-diphenylaminostilbene, 4'-N,N-di(p-methoxyphenyl)aminostilbene, N,
N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine, 3,3'-dimethyl-N,N,N',N'- Examples include benzidine compounds such as tetrakis(4-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine, which are incorporated into the binder resin. Furthermore, poly-N-vinylcarbazole, halogenated poly-N-vinylcarbazole,
Photoconductive polymers include polyvinylanthracene, poly-9-vinylphenylanthracene, polyvinylpyrene, polyvinylacridine, polyvinylacenaphthylene, polyglycidylcarbazole, pyrene-formaldehyde resin, ethylcarbazole-formaldehyde resin, etc. It may also form a layer by itself. In the present invention, it is preferable that the photosensitive layer has a laminated structure because the sensitivity of the electrophotographic photoreceptor is high and the residual potential is low. In this case, the charge generation layer may be formed by dispersing the bisazo compound in the binder resin as described above, but it may also be formed by sublimation or vapor deposition of the bisazo compound. Further, either a charge generation layer or a charge transport layer may be provided as an upper layer; when a charge generation layer is provided as an upper layer, the electrophotographic photoreceptor is of a positively charged type, and when a charge transport layer is provided as an upper layer It can be used as a negatively charged type. In the electrophotographic photoreceptor of the present invention, an adhesive layer may be provided between the photosensitive layer and the conductive support.
The adhesive layer is made of commonly used synthetic resin such as polyester, and is usually formed to have a thickness of about 0.5 to 5 μm. Examples Hereinafter, the present invention will be explained using examples. Example 1 1 part by weight of polyvinyl butyral resin (trade name: BLX Sekisui Chemical Co., Ltd.) was dissolved in 40 parts by weight of cyclohexanone, 3 parts by weight of Exemplary Compound No. 1 was mixed therein, and then mixed in a paint shaker. After being well dispersed, this was applied onto an aluminum sheet using an applicator and dried to form a charge generation layer. The film thickness after drying was 0.2 μm. N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,
1 part by weight of 1'-biphenyl]-4,4'-diamine,
Polycarbonate resin (product name: Lexan 145,
A homogeneous solution consisting of 1 part by weight (manufactured by GE, molecular weight 35.000-40.000) and 15 parts by weight of dichloromethane was applied with an applicator and dried to form a charge transport layer. The film thickness was 20 μm. The electrophotographic photoreceptor thus obtained was tested using an electrostatic copying paper tester (SP-428 manufactured by Kawaguchi Denki Seisakusho).
The following characteristics were evaluated using First, -
After applying 6KV corona charging and negatively charging,
Leave it in the dark for 2 seconds, then the surface potential Vpo
(volt), then irradiate the surface with light using a tungsten lamp so that the illumination intensity is 5 lux, find the time until the surface potential becomes 1/2 of Vpo, and calculate the exposure amount E1 /2 (lux・sec) was calculated. Furthermore, similar measurements were repeated 20 times. The results are shown in Table 1.
【表】
実施例 ２〜10
実施例１において、例示化合物No.1の代わり
に例示化合物No.2，５，16，19，27，28，33，
38，41（それぞれ実施例２〜10）を用いた以外は、
実施例１と同様にして電子写真感光体を作製し、
その特性評価を行つた。
結果は第２表に示す通りである。[Table] Examples 2 to 10 In Example 1, Exemplary Compound No. 2, 5, 16, 19, 27, 28, 33,
38 and 41 (Examples 2 to 10, respectively) were used.
An electrophotographic photoreceptor was produced in the same manner as in Example 1,
We evaluated its characteristics. The results are shown in Table 2.
【表】
発明の効果
本発明の電子写真感光体は、前記ビスアゾ化合
物を用いて構成されているから、従来の有機系光
導電性物質を用いた電子写真感光体に比して、感
度及び耐久性の点で優れたものとなつている。[Table] Effects of the Invention Since the electrophotographic photoreceptor of the present invention is constructed using the bisazo compound, it has higher sensitivity and durability than electrophotographic photoreceptors using conventional organic photoconductive substances. It is superior in terms of sex.
Claims (1)
子を環内に含む二価の複素環基を示し、Ｘは水素
原子又は塩素原子を示し、Cpは 【式】【式】 【式】 及び【式】 の中から選ばれる基を示す。（ここで、Ｙは置換
又は未置換の炭素環式芳香族環、又は置換又は未
置換の複素環式芳香族環を構成するに必要な原子
団を示し、Ｚは置換又は未置換のカルバモイル
基、置換又は未置換のスルフアモイル基、又は置
換又は未置換の複素５員環基を示し、R1は水素
原子、置換又は未置換のアルキル基、置換又は未
置換のアミノ基、置換又は未置換のカルバモイル
基、置換又は未置換のスルフアモイル基、カルボ
キシル基又はそのエステル基を示し、R2は置換
又は未置換のアリール基、又は置換または未置換
のアルキル基を示し、R3は置換又は未置換のア
リール基、置換又は未置換のアルキル基、又は置
換又は未置換の複素環基を示す。）］ で表わされるビスアゾ化合物を含有する感光層を
有することを特徴とする電子写真感光体。[Claims] 1. On a conductive support, the following general formula [Wherein, A represents a divalent aromatic hydrocarbon group or a divalent heterocyclic group containing a nitrogen atom in the ring, X represents a hydrogen atom or a chlorine atom, and Cp represents [Formula] [Formula] [ Indicates a group selected from formula] and [formula]. (Here, Y represents an atomic group necessary to constitute a substituted or unsubstituted carbocyclic aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring, and Z represents a substituted or unsubstituted carbamoyl group. , a substituted or unsubstituted sulfamoyl group, or a substituted or unsubstituted 5-membered heterocyclic group, R 1 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted It represents a carbamoyl group, a substituted or unsubstituted sulfamoyl group, a carboxyl group, or an ester group thereof, R 2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group, and R 3 represents a substituted or unsubstituted alkyl group. aryl group, substituted or unsubstituted alkyl group, or substituted or unsubstituted heterocyclic group)] An electrophotographic photoreceptor comprising a photosensitive layer containing a bisazo compound represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13817386A JPS62295060A (en) | 1986-06-16 | 1986-06-16 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13817386A JPS62295060A (en) | 1986-06-16 | 1986-06-16 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62295060A JPS62295060A (en) | 1987-12-22 |
| JPH0515263B2 true JPH0515263B2 (en) | 1993-03-01 |
Family
ID=15215745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13817386A Granted JPS62295060A (en) | 1986-06-16 | 1986-06-16 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62295060A (en) |
-
1986
- 1986-06-16 JP JP13817386A patent/JPS62295060A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62295060A (en) | 1987-12-22 |
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