JPS62296147A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS62296147A JPS62296147A JP13932586A JP13932586A JPS62296147A JP S62296147 A JPS62296147 A JP S62296147A JP 13932586 A JP13932586 A JP 13932586A JP 13932586 A JP13932586 A JP 13932586A JP S62296147 A JPS62296147 A JP S62296147A
- Authority
- JP
- Japan
- Prior art keywords
- group
- layer
- substituted
- formula
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 32
- 239000000049 pigment Substances 0.000 claims abstract description 31
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 48
- 239000000126 substance Substances 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 239000010410 layer Substances 0.000 abstract description 48
- 239000000463 material Substances 0.000 abstract description 10
- 230000035945 sensitivity Effects 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract description 5
- 150000002367 halogens Chemical class 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000002356 single layer Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 230000032258 transport Effects 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 17
- -1 hydrazone compound Chemical class 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 150000002430 hydrocarbons Chemical group 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 125000004663 dialkyl amino group Chemical group 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 2
- BZKRKPGZABEOSM-XMHGGMMESA-N 4-[(e)-2-[3-[4-(diethylamino)phenyl]-2-phenyl-3,4-dihydropyrazol-5-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1\C=C\C1=NN(C=2C=CC=CC=2)C(C=2C=CC(=CC=2)N(CC)CC)C1 BZKRKPGZABEOSM-XMHGGMMESA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 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
- 150000001412 amines Chemical class 0.000 description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- OHUWRYQKKWKGKG-UHFFFAOYSA-N formaldehyde;pyrene Chemical compound O=C.C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 OHUWRYQKKWKGKG-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UBCHPRBFMUDMNC-AAWJQDODSA-N (1r)-1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1([C@H](N)C)C3 UBCHPRBFMUDMNC-AAWJQDODSA-N 0.000 description 1
- AOLUMCPVEUKWBX-UHFFFAOYSA-N 1-[2-[2-[2-(2,4-dimethoxyphenyl)ethenyl]phenyl]ethenyl]-2,4-dimethoxybenzene Chemical compound COC1=CC(OC)=CC=C1C=CC1=CC=CC=C1C=CC1=CC=C(OC)C=C1OC AOLUMCPVEUKWBX-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- LOEGDFNFPCKHQQ-UHFFFAOYSA-N 1-ethyl-9h-carbazole-3-carbaldehyde Chemical compound N1C2=CC=CC=C2C2=C1C(CC)=CC(C=O)=C2 LOEGDFNFPCKHQQ-UHFFFAOYSA-N 0.000 description 1
- VDFKURANQKCOAI-UHFFFAOYSA-N 1-nitrofluoren-9-one Chemical compound C12=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] VDFKURANQKCOAI-UHFFFAOYSA-N 0.000 description 1
- LSTQIAKIICNSMB-UHFFFAOYSA-N 2-[4-(diethylamino)phenyl]ethenone Chemical compound CCN(CC)C1=CC=C(C=C=O)C=C1 LSTQIAKIICNSMB-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- JNGDCMHTNXRQQD-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarbonitrile Chemical compound O=C1C(C#N)=C(C#N)C(=O)C(C#N)=C1C#N JNGDCMHTNXRQQD-UHFFFAOYSA-N 0.000 description 1
- NIZIGUQDQIALBQ-UHFFFAOYSA-N 4-(2,2-diphenylethenyl)-n,n-diphenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 NIZIGUQDQIALBQ-UHFFFAOYSA-N 0.000 description 1
- PLVXCTLGYWKUAY-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethenyl)-n,n-diphenylaniline Chemical compound C=1C=CC2=CC=CC=C2C=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 PLVXCTLGYWKUAY-UHFFFAOYSA-N 0.000 description 1
- GAYAMEKFIBYRJW-UHFFFAOYSA-N 4-(fluoren-9-ylidenemethyl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=C1C2=CC=CC=C2C2=CC=CC=C21 GAYAMEKFIBYRJW-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
- AEEHOVNCLFTKTO-UHFFFAOYSA-N 4-[[benzyl(phenyl)hydrazinylidene]methyl]-n,n-diphenylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)N=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 AEEHOVNCLFTKTO-UHFFFAOYSA-N 0.000 description 1
- SBMCZDLOXDWNIN-UHFFFAOYSA-N 4-[bis[4-(diethylamino)phenyl]methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)C1=CC=C(N(CC)CC)C=C1 SBMCZDLOXDWNIN-UHFFFAOYSA-N 0.000 description 1
- QGJXVBICNCIWEL-UHFFFAOYSA-N 9-ethylcarbazole-3-carbaldehyde Chemical compound O=CC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 QGJXVBICNCIWEL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LWRSYTXEQUUTKW-UHFFFAOYSA-N DMB Natural products COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- ZNJZXPAUSAGPSA-UHFFFAOYSA-N N,N-diethyl-2-(1,3,4-oxadiazol-2-yl)aniline Chemical compound CCN(CC)C1=CC=CC=C1C1=NN=CO1 ZNJZXPAUSAGPSA-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- MUBKMWFYVHYZAI-UHFFFAOYSA-N [Al].[Cu].[Zn] Chemical compound [Al].[Cu].[Zn] MUBKMWFYVHYZAI-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- WSOJIQBCVMSHLB-UHFFFAOYSA-N indeno[1,2-b]thiophen-4-one Chemical compound C12=CC=CC=C2C(=O)C2=C1SC=C2 WSOJIQBCVMSHLB-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GACNTLAEHODJKY-UHFFFAOYSA-N n,n-dibenzyl-4-[1-[4-(dibenzylamino)phenyl]propyl]aniline Chemical compound C=1C=C(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(CC)C(C=C1)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 GACNTLAEHODJKY-UHFFFAOYSA-N 0.000 description 1
- DXYYLUGHPCHMRQ-UHFFFAOYSA-N n,n-diphenyl-4-(2-phenylethenyl)aniline Chemical compound C=1C=CC=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 DXYYLUGHPCHMRQ-UHFFFAOYSA-N 0.000 description 1
- UAVOVDWXWRXKPS-UHFFFAOYSA-N n-[(4-methoxyphenyl)methylideneamino]-n-methylaniline Chemical compound C1=CC(OC)=CC=C1C=NN(C)C1=CC=CC=C1 UAVOVDWXWRXKPS-UHFFFAOYSA-N 0.000 description 1
- QYXUHIZLHNDFJT-UHFFFAOYSA-N n-[(9-ethylcarbazol-3-yl)methylideneamino]-n-methylaniline Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=NN(C)C1=CC=CC=C1 QYXUHIZLHNDFJT-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002401 polyacrylamide Polymers 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
- 150000003071 polychlorinated biphenyls Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920006215 polyvinyl ketone Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
技術分野
本発明は電子写真用の感光体に関し、さらに詳しくは、
元を照射したとき電荷担体を発生する物質（以下「電荷
発生物質」という）としてビスアゾ顔料を含有する感光
層を設けた電子写真用感光体に関する。DETAILED DESCRIPTION OF THE INVENTION Technical Field The present invention relates to a photoreceptor for electrophotography, and more particularly, to a photoreceptor for electrophotography.
The present invention relates to an electrophotographic photoreceptor provided with a photosensitive layer containing a bisazo pigment as a substance that generates charge carriers when irradiated with a material (hereinafter referred to as "charge-generating material").
従来技術
電子写真用の感光体として、無機物系のものではセレン
及びその合金を用いたもの、あるいは色素増感した酸化
亜鉛を結着樹脂中に分散した感光体などが、また有機物
系のものでは２゜４ 、 ’ｒ −） ＋）ニトロ−９
−フルオレノン（以下「Ｔ Ｎ ＰＪという）とポリ−
Ｎ−ビニルカルバゾール（以下「ＰＶＫＪという）との
電荷移動錯体を用いたものなどが代表的なものとして知
られている。PRIOR ART Photoconductors for electrophotography include inorganic photoconductors that use selenium and its alloys, or photoconductors that have dye-sensitized zinc oxide dispersed in a binder resin, and organic photoconductors that use selenium and its alloys. 2゜4, 'r-) +) Nitro-9
-Fluorenone (hereinafter referred to as "TNPJ") and poly-
A typical example is one using a charge transfer complex with N-vinylcarbazole (hereinafter referred to as "PVKJ").
しかし、これらの感光体は多くの長所を持っていると同
時に、さまざまな欠点を持っている。However, while these photoreceptors have many advantages, they also have various disadvantages.
例えば１現在広く用いられているセレン感光体は製造す
る条件がむずかしく、製造コストが高かったり・可撓性
がないためにベルト状に加工することがむずかしく、ま
た熱や機械的な衝撃に鋭敏なため取扱いく注意を要する
。酸化亜鉛感光体は安価な酸化亜鉛を用いて支持体への
塗布で製造することが出来るためコストは低いが、一般
に感度が低かった）、表面の平滑性・硬度−引つ張夛強
度、耐摩擦性などの機械的な欠点があフ、通常反復して
使用する普通紙複写機用の感光体としては耐久性などに
問題が多い。また、ＴＮＦとＰＶＫとの電荷移動錯体を
用いた感光体は感度が低く、高速複写機用の感光体とし
ては不適当である。For example, the currently widely used selenium photoreceptor has difficult manufacturing conditions, is expensive, has no flexibility, and is difficult to process into a belt shape, and is sensitive to heat and mechanical shock. Therefore, care must be taken when handling it. Zinc oxide photoreceptors are low in cost because they can be manufactured by applying inexpensive zinc oxide to a support, but they generally have low sensitivity), surface smoothness/hardness, tensile strength, and durability. It has mechanical drawbacks such as friction, and there are many problems with durability as a photoreceptor for plain paper copying machines, which are usually used repeatedly. Furthermore, a photoreceptor using a charge transfer complex of TNF and PVK has low sensitivity and is unsuitable as a photoreceptor for high-speed copying machines.
近年、これらの感光体の欠点を排除するために広範な研
究が進められ、特に有機物系のさまざまな感光体が提案
されている。中でも、有機顔料の薄膜を導電性支持体上
に形成しく電荷発生層）、この上に電荷搬送物質を主体
とする層（電荷搬送層）を形成した積層型の感光体が従
来の有機物系の感光体に比べ、一般に感度が高く帯電性
が安定していることなどの点から普通紙複写機用の感光
体として注目されておシ、一部実用に供されているもの
がある。In recent years, extensive research has been carried out to eliminate the drawbacks of these photoreceptors, and in particular, various organic photoreceptors have been proposed. Among them, a laminated photoreceptor in which a thin film of an organic pigment is formed on a conductive support (charge generation layer), and a layer mainly composed of a charge transport substance (charge transport layer) is formed on this layer, which is different from conventional organic-based photoreceptors. Compared to photoconductors, they generally have higher sensitivity and stable chargeability, so they have attracted attention as photoconductors for plain paper copying machines, and some of them are in practical use.
この種の従来の積層型の感光体として、（Ｉ）電荷発生
層としてペリレン誘導体を真空蒸着した薄層を用い、電
荷搬送層にオキサジアゾール誘導体を用いたもの（ｎａ
ｐ ３８７１８８２参照）
（２）電荷発生層としてクロルダイアンブルーの有機ア
ミン溶液を塗布して形成した薄層な用い、電荷搬送層に
ヒドラゾン化合物を用いたもの（特公昭５５−４２３８
０号公報参照）などが知られている。This type of conventional laminated photoreceptor uses (I) a thin layer of a perylene derivative vacuum-deposited as a charge generation layer and an oxadiazole derivative as a charge transport layer (na
(See p. 3871882) (2) A thin layer formed by coating an organic amine solution of chlordian blue as the charge generation layer, and a hydrazone compound used as the charge transport layer (Japanese Patent Publication No. 55-4238
(see Publication No. 0) are known.
しかしながら、この種の積層型の感光体においても従来
のものは多くの長所を持っていると同時にさまざまな欠
点を持っていることも事実である。即ち、次のごとき欠
点である。However, it is true that conventional laminated photoreceptors of this type have many advantages, but also have various disadvantages. That is, it has the following drawbacks.
（Ｉ）で示したペリレン誘導体とオキサジアゾール誘導
体とを用いた感光体は、その電荷発生層を真空蒸着によ
〕形成するため製造コストが高くなる。The photoreceptor using the perylene derivative and oxadiazole derivative shown in (I) has a charge generation layer formed by vacuum evaporation, which increases the manufacturing cost.
（２）で示したクロルダイアンブルーとヒドラゾン化合
物とを用いた感光体は、電荷発生層を形成するための塗
布溶剤として１一般に取シ扱いにくい有機アミン（例え
ばエチレンジアミン）を用いる必要があシ、感光体作成
上の欠点が多いＯ
目 的
本発明の目的は加工及び製造が容易で、熱的及び機械的
強度に優れ、しかも高感度で安価な電子写真用感光体を
提供することである。The photoreceptor using chlordiane blue and a hydrazone compound shown in (2) requires the use of an organic amine (e.g. ethylenediamine) which is generally difficult to handle as a coating solvent for forming the charge generation layer. There are many drawbacks in producing a photoreceptor.Objective The object of the present invention is to provide an electrophotographic photoreceptor that is easy to process and manufacture, has excellent thermal and mechanical strength, has high sensitivity, and is inexpensive.
構 成
本発明の電子写真用感光体は、導電性支持体上に、電荷
発生物質として下記一般式（Ｉ）で示されるビスアゾ顔
料を含有する感光層を設けたことを特徴とするものであ
る。Structure The electrophotographic photoreceptor of the present invention is characterized in that a photosensitive layer containing a bisazo pigment represented by the following general formula (I) as a charge generating substance is provided on a conductive support.
（但し人はカップラー残基な表わし、Ｒは同一でも異な
ってもよく、水素原子、ハロゲン原子、置換又は無置換
のアルキル基、置換又は無置換のフルコキシ基、置換又
は無置換のアリール基、ベンゾイル基、シアノ基、置換
アミノ基、ニトロ基、アセチル基、又はカルボキシル基
又はそのエステルを表わし、ｎは１〜４の整数を表わす
。）
一般式（Ｉ）におけるカップラー残基人としては、フェ
ノール類、ナフトール類、アミノナフトール類等の水酸
基及び／又はアミノ基を有する芳香族炭化水素化合物；
水酸基及び／又はアミノ基を有する複素環式化合物；脂
肪族又は芳香族のエノール性ケトン基を有する化合物、
即ち活性メチレン基を有する化合物等の残基が挙げられ
るが、具体的には下記一般式（Ｉ）〜（６）で示される
ものが挙げられる。(However, R represents a coupler residue, R may be the same or different, hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted flukoxy group, substituted or unsubstituted aryl group, benzoyl group, a cyano group, a substituted amino group, a nitro group, an acetyl group, a carboxyl group, or an ester thereof, and n represents an integer of 1 to 4.) The coupler residue in general formula (I) includes phenols; , an aromatic hydrocarbon compound having a hydroxyl group and/or an amino group such as naphthols, aminonaphthols;
Heterocyclic compounds having a hydroxyl group and/or amino group; compounds having an aliphatic or aromatic enolic ketone group;
That is, examples include residues of compounds having active methylene groups, and specific examples include those represented by the following general formulas (I) to (6).
（上記式（Ｉ）、１）、（ト）および（ト）中、ＸＩＹ
ＩＩＺＩｍおよびｎはそれぞれ以下のものを表わす。(In the above formulas (I), 1), (g) and (g), XIY
IIZIm and n each represent the following.
（Ｒ１およびＲ，は水素または置換もしくは無置換のア
ルキルを表わし、拘
は置換もしくは無置換のアルキル基
または置換もしくは無置換のアリー
ル基を表わす。）
Ｙｌ：水素、ハロゲン、置換もしくは無置換のアルキル
基、置換もしくは無置換の
アルコキシ基、カルボキシ基、スルホ
基、置換もしくは無置換のスルファモ
〔几４は水素、アルキル基またはその置換体、フェニル
基またはその置換体
を表わし、Ｙｌは炭化水素環基または
その置換体、複素環基またはその置
Ｒ８は炭化水素環基またはその置換体、複素環基または
その置換体あるいは
スチリル基またはその置換体、−は
水素、アルキル基、フェニル基また
はその置換体を表わすか、あるいは
翫および−はそれらに結合する炭素
原子と共に環を形成してもよいＯ）を
示す◎〕
２：炭化水素環またはその置換体あるいは複素環または
その置換体
ｎ：１または２の整数
ｍ：１または２の整数）
（式（６）および（至）中、階は置換もしくは無置換の
炭化水素基を表わし、Ｘは前記に同じである。）
Ａｒｌ
（式中、馬はアルー＋ル基、カルバモイル基、カルボキ
シル基またはそのエステルな表わし、Ａｒｌは炭化水素
環基またはその置換体を表わし、Ｘは前記と同じである
。）
（上記式（至）および（Ｉ）中、−は水素または置換も
しくは無置換の炭化水素基を表わし、人ｒ！は炭化水素
環基またはその置換体を表わす。）前記一般式（Ｉｆ）
、（Ｉ）、（イ）またＦｉ（７）の２の炭化水素環とし
てはベンゼン環、ナフタレン環などが例示でき、また複
素環としてはインドール環、カルバゾール環、ベンゾフ
ラン環などが例示できる０２の環における置換基として
は塩素原子、臭素原子などのハロゲン原子及びアルコキ
シ基が例示できる。(R1 and R represent hydrogen or substituted or unsubstituted alkyl, and K represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.) Yl: hydrogen, halogen, substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a carboxy group, a sulfo group, a substituted or unsubstituted sulfamo group [几4 represents hydrogen, an alkyl group or a substituent thereof, a phenyl group or a substituent thereof, Yl is a hydrocarbon ring group or a substituent thereof, a heterocyclic group or a substituent thereof R8 is a hydrocarbon ring group or a substituent thereof, a heterocyclic group or a substituent thereof, a styryl group or a substituent thereof, - is hydrogen, an alkyl group, a phenyl group or a substituent thereof ◎] 2: Hydrocarbon ring or its substituted product or heterocycle or its substituted product n: 1 or 2 Integer m: an integer of 1 or 2) (In formulas (6) and (to), the floor represents a substituted or unsubstituted hydrocarbon group, and X is the same as above.) Arl (In the formula, horse is An Ar group, a carbamoyl group, a carboxyl group or an ester thereof, Arl represents a hydrocarbon ring group or a substituted product thereof, and X is the same as above. (In the above formulas (to) and (I), - represents hydrogen or a substituted or unsubstituted hydrocarbon group, and r! represents a hydrocarbon ring group or a substituted product thereof.) General formula (If)
, (I), (A) In addition, examples of the hydrocarbon ring in 2 of Fi(7) include a benzene ring and a naphthalene ring, and examples of the heterocycle include an indole ring, a carbazole ring, and a benzofuran ring. Examples of substituents on the ring include halogen atoms such as chlorine atoms and bromine atoms, and alkoxy groups.
Ｙ！またはＲｓにおける炭化水素環基としては、フェニ
ル基、ナフチル基、アントリル基、ピレニル基などが、
また、複素環基としてはピリジル基、チェニル基、フリ
ル基、インドリル基、ベンゾフラニル基、カルバゾリル
基、ジベンゾ７２ニル基などが例示でき、さらに、−お
よびＲ６が結合して形成する環としては、フルオレン環
などが例示できる。Y! Alternatively, examples of the hydrocarbon ring group in Rs include phenyl group, naphthyl group, anthryl group, pyrenyl group, etc.
Further, examples of the heterocyclic group include a pyridyl group, a chenyl group, a furyl group, an indolyl group, a benzofuranyl group, a carbazolyl group, a dibenzo72yl group, and the ring formed by combining - and R6 with fluorene. An example is a ring.
Ｙ！またはＲ，の炭化水素環基または複素環基あるいは
几５および−によって形成される環における置換基とし
ては、メチル基、エチル基、プロピル基、ブチル基など
のアルキル基、メトキシ基、エトキシ基、プロポキシ基
、ブトキシ基などのアルコキシ基、塩素原子、臭素原子
などのハロゲン原子、ジメチルアミノ基、ジエチルアミ
ノ基などのジアルキルアミノ基、ジベンジルアミノ基な
どのジアラルキルアミノ基、トリフルオロメチル基など
のハロメチル基、ニトロ基、シアノ基、カルボキシル基
またはそのエステル、水酸基、Ｓ ｏ、Ｎａなどのスル
ホン酸塩基などが挙げられる。Y! The substituents on the hydrocarbon cyclic group or heterocyclic group of R, or the ring formed by 5 and - include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, methoxy group, ethoxy group, Alkoxy groups such as propoxy groups and butoxy groups, halogen atoms such as chlorine atoms and bromine atoms, dialkylamino groups such as dimethylamino groups and diethylamino groups, dialkylamino groups such as dibenzylamino groups, and halomethyl groups such as trifluoromethyl groups. group, nitro group, cyano group, carboxyl group or its ester, hydroxyl group, and sulfonic acid groups such as So and Na.
几４のフェニル基の置換体としては塩素原子または臭素
原子などのハロゲン原子が例示できる。Examples of substituents for the phenyl group of 几4 include halogen atoms such as chlorine atoms and bromine atoms.
％または為における炭化水素基の代表例としては、メチ
ル基、エチル基、プロピル基、ブチル基などのアルキル
基、ベンジル基などのアラルキル基、フェニル基などの
アリール基またはこれらの置換体が例示できる。Typical examples of hydrocarbon groups in % or so include alkyl groups such as methyl, ethyl, propyl, butyl, aralkyl groups such as benzyl, aryl groups such as phenyl, or substituted products thereof. .
Ｒ？またはへの炭化水素基における置換基としては、メ
チル基、エチル基、プロピル基、ブチル基などのアルキ
ル基、メトキシ基、エトキシ基、プロポキシ基、ブトキ
シ基などのアルコキシ基、塩素原子、臭素原子などのハ
ロゲン原子、水酸基、ニトロ基などが例示できる。R? Examples of substituents on hydrocarbon groups include methyl, ethyl, propyl, butyl, and other alkyl groups, methoxy, ethoxy, propoxy, and butoxy, and other alkoxy groups, chlorine, bromine, etc. Examples include halogen atoms, hydroxyl groups, and nitro groups.
人ｒ１″ｉ！たは人ｒｌにおける炭化水素環基としては
、フェニル基、ナフチル基などがその代表例であり、ま
た、これらの基における置換基としては、メチル基、エ
チル基、プロピル基、ブチル基などのアルキル基、メト
キシ基、エトキシ基、プロポキシ基、ブトキシ基などの
アルコキシ基、ニトロ基、塩素原子、臭素原子などのハ
ロゲン原子、シアン基、ジメチルアミノ基、ジエチルア
ミン基などのジアルキルアミノ基などが例示できる。Typical examples of the hydrocarbon ring group in human r1''i! or human rl are phenyl group, naphthyl group, etc., and substituents on these groups include methyl group, ethyl group, propyl group, Alkyl groups such as butyl groups, alkoxy groups such as methoxy groups, ethoxy groups, propoxy groups, butoxy groups, halogen atoms such as nitro groups, chlorine atoms, bromine atoms, dialkylamino groups such as cyan groups, dimethylamino groups, diethylamine groups, etc. For example,
また、Ｘの中では特に水酸基が適当である。Furthermore, among X, a hydroxyl group is particularly suitable.
上記カップラー残基の中でも好ましいのは上記一般式（
Ｉ）、（６）、（ト）、６１Ｅｌ 、（Ｉ）および（Ｉ
）で示されるものであシ、この中でも一般式におけるＸ
が水酸基のものが好ましい。また、この中でも一般式（
至）
（ＹＸおよびＺは前記に同じ。）
で表わされるカップラー残基が好ましく、さらに好まし
くは一般式（至）
（Ｚ 、 Ｙ、およびＲ，は前記に同じ。）で示される
カップ２−残基である。Among the above coupler residues, preferred is the general formula (
I), (6), (g), 61El, (I) and (I
), and among these, X in the general formula
is preferably a hydroxyl group. Also, among these, the general formula (
to) (YX and Z are the same as above) A coupler residue represented by the following is preferable, more preferably a cup 2-residue represented by the general formula (to) (Z, Y, and R are the same as above) It is the basis.
さらにまた、上記好ましいカップラー残基の中でも一般
式（３）または（至）
”−ｚ’”
（ｚ＋ｋ ＊ Ｒ＠および−は前記に同じであムまだＲ
ｌｏとしては上記のＹ８の置換基が例示できる。）
で表わされるものが適当でちる。Furthermore, among the above preferred coupler residues, general formula (3) or (to) "-z'" (z+k * R@ and - are the same as above, but still R
As lo, the above-mentioned substituent Y8 can be exemplified. ) is appropriate.
以上のような本発明に用いるビスアゾ囚料の具体例を構
造式で示すと次の通りである。Specific examples of the bisazo prisoner used in the present invention as described above are shown in the following structural formula.
（以下余白）
（以下余白）
Ｒ１００
ａｐ −Ｎ＝Ｎ−Ｄ−Ｎ−Ｎ−ｃｐ
本発明で用いられる前記一般式（Ｉ）のビスアゾ顔料は
下記反応式に示すように、まず式（ＸＶ）の２，７−シ
ニトロー９．１ｏ−７エナントレンキノンと式（ＸＶＩ
）のオルトフェニレンジアミン誘導体（式中Ｂは一般式
（Ｉ）のＲＫ同じ）とを脱水縮合して一般式（Ｘ■）で
示されるフェナジ／のジニトロ誘導体とし、とのジニト
ロ体を還元して一般式（Ｘｔｌ）で示されるジアミノ体
とし１ついでこれをジアゾ化して一般式（ＸＩ）で示さ
れるジアゾニウム塩化合物（式中Ｙはアニオン官能基）
とし、更にこれをＮ、Ｎ−ジメチルホルムアミド（ｐＭ
Ｆ）のような有機溶媒中、武人Ｈ（人は一般式（Ｉ）の
人に同じ）で示されるカップラーとカップリング反応さ
せることにより容易に製造することができる。その例と
して以下に前記Ａ１のビスアゾ顔料の製造例を示すが、
他のビスアゾ顔料もカップラーを変える他はこの製造例
に従って容易に製造することができる。(Hereinafter in the margin) (Hereinafter in the margin) R100 ap -N=N-D-N-N-cp As shown in the reaction formula below, the bisazo pigment of the general formula (I) used in the present invention is first converted to the formula (XV). 2,7-sinitro9.1o-7 enanthrenequinone and the formula (XVI
) with an orthophenylenediamine derivative (in the formula, B is the same as RK in general formula (I)) to obtain a dinitro derivative of phenazi/ represented by general formula (X), and reduce the dinitro derivative of A diazonium salt compound represented by the general formula (XI) obtained by forming a diamino compound represented by the general formula (Xtl) and then diazotizing it (wherein Y is an anionic functional group)
and further diluted with N,N-dimethylformamide (pM
It can be easily produced by a coupling reaction with a coupler represented by Takehito H (whose name is the same as the person of general formula (I)) in an organic solvent such as F). As an example, the production example of the bisazo pigment of A1 is shown below.
Other bisazo pigments can also be easily produced according to this production example, except for changing the coupler.
（罵） （ｆｆ）
製造例
２．７−シニトロー９．１０−７エナントレンキノン３
．６０１！（０，０１２１モル）及びオルトフェニレン
ジアミンＬ９６ Ｆ （０，０１８１モル）にビヘリシ
ン１滴及びオルトジクロルベンゼン２００ｄを加え、１
０分間加熱還流した。放冷後、析出した結晶なｒ取し、
メタノール１００ｄで洗浄乾燥して４．３６．９の黄色
結晶を得た。これを約４００−のオルトジクロルベンゼ
ンで再Ｍ晶して３．４４ｊｌ（収率７６．８％）の精製
品（黄色針状結晶）を得た。このものの融点は３００Ｃ
以上で、また元素分析値は下記の通フであった。これら
のデータからこの結晶が一般式（Ｘ［）においてＲ１＝
Ｈ１ｎ＝１のジニトロ化合物であることが確認された。(Expletive) (ff) Production Example 2.7-Sinitro 9.10-7 Enanthrenequinone 3
．． 601! (0,0121 mol) and orthophenylenediamine L96 F (0,0181 mol) were added with 1 drop of bihelysin and 200 d of orthodichlorobenzene, and 1
The mixture was heated to reflux for 0 minutes. After cooling, remove the precipitated crystals,
After washing with 100 d of methanol and drying, yellow crystals of 4.36.9 were obtained. This was recrystallized with about 400-orthodichlorobenzene to obtain 3.44 jl (yield 76.8%) of a purified product (yellow needle-like crystals). The melting point of this thing is 300C
In addition, the elemental analysis values were as follows. From these data, this crystal has the general formula (X[) with R1=
It was confirmed that it was a dinitro compound with H1n=1.
元素分析値：
計算値 実測値
０％ ６４．８６ ６５．００Ｈ％
２．７２ ２．７４Ｎ％
１５．１３ １５．０４次にこのジニトロ化
合物２．６５７（７，１６Ｘ１０−”モル）を３５％塩
酸水溶液７０ｘｌに分散し、８ｎＯｊｌ。Elemental analysis value: Calculated value Actual value 0% 64.86 65.00H%
2.72 2.74N%
15.13 15.04 Next, 2.657 (7,16 x 10-'' moles) of this dinitro compound was dispersed in 70 x l of a 35% aqueous hydrochloric acid solution, and 8 nOjl.
２Ｈ禽０１２．２．！１ｌ（０，５０２９モル）を添加
した後、約８０Ｇで１時間攪拌し、反応させた。放冷後
、得られた沈澱をＦ取し、この沈澱物に本釣２５０１を
加え、更に水酸化ナトリウムを強アルカリ性になるまで
加え、充分攪拌した後、沈澱物を再びｒ取し、水洗した
後、乾燥してＬ２２ＪＩの黒紫色結晶を得た。これを更
にオルトジクロルベンゼン約ｔ ＯＯａｕ及びニトロベ
ンゼン約１００−からなる混合溶媒で再結晶し、１．９
０！ｉの精製品（黒紫色針状結晶）を得た。このものは
融点３ｏｏｃ以上で、また元素分析値は下記の通りであ
った。これらのデータからこの結晶が一般式（ｘ′ＶＩ
）にオイテＲ１＝Ｈ、！ｌ ＝ １ （７）シフｔ／化
合物であることがｒ４詔された。2H bird012.2. ! After adding 1 liter (0,5029 mol), the mixture was stirred at about 80 G for 1 hour to react. After cooling, the obtained precipitate was collected in F, and Honsuri 2501 was added to this precipitate, and sodium hydroxide was further added until it became strongly alkaline. After stirring thoroughly, the precipitate was collected in R again and washed with water. After that, it was dried to obtain black-purple crystals of L22JI. This was further recrystallized with a mixed solvent consisting of about t OOau of orthodichlorobenzene and about 100 t of nitrobenzene.
0! A purified product of i (black-purple needle-like crystals) was obtained. This product had a melting point of 3 ooc or more, and the elemental analysis values were as follows. From these data, this crystal has the general formula (x'VI
) to OiteR1=H,! l = 1 (7) It was ruled that r4 is a shift t/compound.
元素分析値工
計算値 実測値
０％ ７７．４０ ７６．９５Ｈ≦
４５５ ４４８Ｎ％
１ｇ、０５ １
フ、７４次にコノジアミノ化合物１．５８ＪＦ（５，０
９ＸＩＱ−”そル）Ｋ水１００ｇｊ及び２Ｇ襲塩酸水溶
液ｉｏ。Elemental analysis value Engineering calculation value Actual value 0% 77.40 76.95H≦
455 448N%
1g, 05 1
F, 74 then conodiamino compound 1.58JF (5,0
9XIQ-"Solu) K water 100gj and 2G hydrochloric acid aqueous solution io.
ｄを加え、室温で３０分間攪拌溶解した後、この溶液を
２〜３Ｃに冷却しながら、この中に、亜硝酸す） ＩＪ
ウム（純度９７％） ０．７４ Ｆを水Ｓ−に溶解した
溶液を２分間に亘って滴下、反応させた。その後、前記
温度で３０分間攪拌した後、反応液を濾過し、Ｐ液に４
２％硼弗化水素酸水溶液１２ゴを加え、析出した結晶を
ｒ取し、メタノールで洗浄した後、乾燥して２．３８１
の黄色結晶を得た。このものは赤外線吸収スペクトル（
Ｋｍｒ錠剤法）において２３ｏｏｃｒ１Ｍ−１にジアゾ
ニウム基に基づく吸収が認められたので、一般式（Ｘｉ
［）においてＲ４＝ Ｈｌｎ ＝ １ 、 Ｙ＝Ｂ Ｐ
４のジアゾニウム塩化合物であることが確認された。After adding d and stirring and dissolving at room temperature for 30 minutes, add nitrous acid into the solution while cooling it to 2-3C) IJ
A solution of 0.74 F (purity 97%) in water S- was added dropwise over 2 minutes to cause a reaction. Thereafter, after stirring at the above temperature for 30 minutes, the reaction solution was filtered, and 4
Add 12% 2% aqueous borohydrofluoric acid solution, collect the precipitated crystals, wash with methanol, and dry to give 2.381
Yellow crystals were obtained. This one has an infrared absorption spectrum (
In the general formula (Xi
In [), R4= Hln = 1, Y=B P
It was confirmed that it was a diazonium salt compound of No. 4.
次にこのジアゾニウム塩化合物１．２７１９ （０，０
０２５モル）及びカップラーとして２−ヒドロキシ−３
−す７トエ酸アニリド１．３２Ｎ（０，００５モル）を
、冷却したＤＭＦ２５０ｓｌＫ溶解し、これに１０．５
％酢酸ナトリウム水溶液８ｄを５〜ＩＯＣの温度で５分
間に亘って滴下し、ついで室温で２時間攪拌しカップリ
ング反応を行なった。Next, this diazonium salt compound 1.2719 (0,0
025 mol) and 2-hydroxy-3 as coupler
-1.32N (0,005 mol) of 7toic acid anilide was dissolved in 250 slK of cooled DMF, and 10.5
% aqueous sodium acetate solution was added dropwise over 5 minutes at a temperature of 5 to IOC, and then stirred at room temperature for 2 hours to carry out a coupling reaction.
生成した沈澱をｆ取し、８０ＣＫ加熱したＤＭＦ２００
ｄで３回洗浄し、更に水２００−で２回洗浄した後、１
２０１Ｚ’の温度で減圧乾燥して緑葉色粉１．２８１
（収率５９．６≦）を得た。このものの融点は３００Ｃ
以上で、元素分析値は下記の通りであった。The generated precipitate was collected and heated to 80CK in DMF200.
After washing 3 times with d and 2 times with water 200-
Dry under reduced pressure at a temperature of 201Z' to obtain green leaf colored powder 1.281
(Yield 59.6≦) was obtained. The melting point of this thing is 300C
The elemental analysis values were as follows.
元素分析値：
計算値 実測値
０％ ７５．５１ ７５．２２Ｈ％
３．９９ ３．７６Ｈ％
１３．０Ｂ １２．７３これらのデータ及
び別途に測定した赤外線吸収スペクトル（ＫＢｒ法）か
らこの粉末は化合物Ａ１のビスアゾ化合物であることが
確認された。Elemental analysis value: Calculated value Actual value 0% 75.51 75.22H%
3.99 3.76H%
13.0B 12.73 From these data and a separately measured infrared absorption spectrum (KBr method), it was confirmed that this powder was a bisazo compound of Compound A1.
本発明の電子写真用感光体ではビスアゾ顔料は感光層に
おける電荷発生物質として用いられ、この感光体の代表
的な構成を第１図およびＲ２図に示した。In the electrophotographic photoreceptor of the present invention, a bisazo pigment is used as a charge generating substance in the photosensitive layer, and a typical structure of this photoreceptor is shown in FIGS. 1 and R2.
第１図の感光体は、導電性支持体１１上に、ビスアゾ顔
料１３を主体とする電荷発生Ｎｘｓと電荷搬送物質を主
体とする電荷搬送層１７とからなる積層型の感光層１９
１を設けたものであるＯ
第１図の感光体では、像露光された光は電荷搬送層を透
過し、電荷発生層１５に到達し、その部分のビスアゾ顔
料１３で電荷の生成が起こ）、一方、電荷搬送層１７は
電荷の注入を受けその搬送を行なうもので、光減衰に必
要な電荷の生成はビスアゾ顔料１３で行なわれ、また電
荷の搬送は電荷搬送層１７でというメカニズムである。The photoreceptor shown in FIG. 1 has a laminated photosensitive layer 19 on a conductive support 11, which is composed of a charge generating Nxs mainly composed of a bisazo pigment 13 and a charge transporting layer 17 mainly composed of a charge transporting substance.
In the photoreceptor shown in FIG. 1, imagewise exposed light passes through the charge transport layer and reaches the charge generation layer 15, where generation of charges occurs in the bisazo pigment 13). On the other hand, the charge transport layer 17 receives charge injection and transports it, and the mechanism is such that the charge necessary for light attenuation is generated by the bisazo pigment 13, and the charge is transported by the charge transport layer 17. .
第２図の感光体は導電性支持体１１上に主としてビスア
ゾ顔料１３、電荷搬送物質および絶縁性結合剤からなる
感光層１９２を設けたものである。ここでもビスアゾ顔
料１３は電荷発生物質である〇
その他の感光体として第１図の電荷発生層と電荷搬送層
を逆にすることも可能である。The photoreceptor shown in FIG. 2 has a photosensitive layer 192 mainly composed of a bisazo pigment 13, a charge transport substance, and an insulating binder provided on a conductive support 11. The photoreceptor shown in FIG. Here again, the bisazo pigment 13 is a charge-generating substance.Other photoreceptors may be used in which the charge-generating layer and the charge-transporting layer shown in FIG. 1 are reversed.
感光層の厚さは、第１図のもので電荷発生層１５の厚み
は好ましくは０．０１〜５μさらに好ましくは０．０５
〜２μである。この厚さが０．０１μ以下であると電荷
の発生は十分ではなく、また５μ以上であると残留電位
が高く実用に耐えない。電荷搬送ＮＪ１７の厚さは好ま
しくは３〜５０μ、さらに好ましくは５〜２０μである
。The thickness of the photosensitive layer is as shown in FIG. 1, and the thickness of the charge generation layer 15 is preferably 0.01 to 5μ, more preferably 0.05μ.
~2μ. If the thickness is less than 0.01 μm, charge generation will not be sufficient, and if it is more than 5 μm, the residual potential will be too high for practical use. The thickness of the charge transport NJ17 is preferably 3-50μ, more preferably 5-20μ.
この厚さが３μ以下であると帯電量が不十分であＪ、５
０μ以上であると残留電位が高く実用的ではない。If this thickness is less than 3μ, the amount of charge will be insufficient.J,5
If it is 0μ or more, the residual potential is high and it is not practical.
電荷発生層１５は前記の一般式で示されるビスアゾ顔料
を主体とし、さらに結合剤、可Ｉ剤などを含有すること
ができる。また、電荷発生層中のビスアゾ顔料の割合は
好ましくは３０重量％以上、さらに好ましくは５０重量
％以上である０
電荷搬送層１７は電荷搬送物質と結合剤を主体とし、さ
らに可塑剤などを含有することができる。電荷搬送層中
の電荷搬送物質の割合は１０〜９５重量％、好ましくは
３０〜９０ｆｉ量−である。電荷搬送物質の占める割合
がＩＱ重量％未満であると、電荷の搬送はほとんど行な
われず、また９５重量％以上であると感光体皮膜の機械
的強度が極めて悪く実用に供しえない〇第２図に示した
感光体の場合は、感光層１９２の厚さは好ましくは３〜
５０μ、さらに好ましくは５〜２０μであ乞。ずた、感
光Ｎ１９２中のビスアゾ顔料の割合は好ましくは５０重
量％以下、さらに好ましくＦｉ２０重量％以下であｐｌ
また電荷搬送物質の割合は好ましくＩＩ′ｉ１０〜９５
重量％、さらに好ましくは３０〜９０重量％である。The charge generation layer 15 is mainly composed of a bisazo pigment represented by the above general formula, and may further contain a binder, a lubricating agent, and the like. The proportion of the bisazo pigment in the charge generation layer is preferably 30% by weight or more, more preferably 50% by weight or more. The charge transporting layer 17 is mainly composed of a charge transporting substance and a binder, and further contains a plasticizer. can do. The proportion of charge transport material in the charge transport layer is from 10 to 95% by weight, preferably from 30 to 90 fi amount. If the proportion of the charge transport substance is less than IQ weight %, almost no charge is transported, and if it is more than 95 weight %, the mechanical strength of the photoreceptor film is extremely poor and cannot be put to practical use. In the case of the photoreceptor shown in , the thickness of the photosensitive layer 192 is preferably 3 to 3.
50μ, more preferably 5 to 20μ. The proportion of bisazo pigment in photosensitive N192 is preferably 50% by weight or less, more preferably Fi 20% by weight or less.
The proportion of the charge transport substance is preferably II'i10 to 95.
% by weight, more preferably 30 to 90% by weight.
本発明は、電子写真用感光体における電荷発生物質とし
て、前記一般式（Ｉ）で表わされる特定のビスアゾ顔料
を用いることを特徴とするものでちゃ、導電性支持体、
電荷搬送物質など他の構成要素としては従来知られてい
たもののいずれもが使用できるが、それらについて以下
に具体的に説明する。The present invention is characterized in that a specific bisazo pigment represented by the general formula (I) is used as a charge generating substance in an electrophotographic photoreceptor, a conductive support,
Any conventionally known components such as charge transport materials can be used, and these will be specifically explained below.
本発明の感光体において使用される導電性支持体として
は、アルミニウム、銅、亜鉛等の金属板、ポリエステル
等のプラスチックシートまたはプラスチックフィルムに
アルミニウム、Ｓａｕｇ等の導電材料を蒸着したもの、
あるいは導電処理した紙等が使用される。Examples of the conductive support used in the photoreceptor of the present invention include a metal plate made of aluminum, copper, zinc, etc., a plastic sheet or plastic film made of polyester, etc., on which a conductive material such as aluminum, Saug, etc. is vapor-deposited;
Alternatively, conductive treated paper or the like may be used.
結合剤としては、ポリアミド、ポリウレタン、ポリエス
テル、エポキシ樹脂、ポリケトン、ポリカーボネートな
どの縮合系樹脂やポリビニルケトン、ボリスチレ／、ポ
リ−Ｎ−ビニルカルバゾール、ポリアクリルアミドなど
のビニル重合体などが挙げられるが、絶縁性で且つ接着
性のある樹脂は全て使用できる。Examples of binders include condensation resins such as polyamide, polyurethane, polyester, epoxy resin, polyketone, and polycarbonate, and vinyl polymers such as polyvinyl ketone, polystyrene, poly-N-vinyl carbazole, and polyacrylamide. Any resin that is flexible and has adhesive properties can be used.
可塑剤としては、ハロゲン化パラフィン、ポリ塩化ビフ
ェニル、ジメチルナフタレン、ジブチルフタレートなど
が挙げられる。その他感光体の表面性をよくするために
シリコンオイル等を加えてもよい。Examples of plasticizers include halogenated paraffins, polychlorinated biphenyls, dimethylnaphthalene, and dibutyl phthalate. In addition, silicone oil or the like may be added to improve the surface properties of the photoreceptor.
電荷搬送物質には正孔搬送物質と電子搬送物質がある。Charge transport materials include hole transport materials and electron transport materials.
正孔搬送物質としては、たとえば以下の一般式（Ｉ）〜
（社）Ｋ示されるような化合物が例示できる。As the hole transport substance, for example, the following general formulas (I) to
Examples include compounds such as those shown by K.
〔式中、Ｒ１１ｌはメチル基、エチル基、２−ヒドロキ
クエチル基３１２−クロルエチル基を表わし％ Ｉ’Ｌ
ｔｔｓはメチル基、エチル基、ベンジル基又はフェニル
基を表わし、ＲＩＭは水素、塩素、臭素、炭素数１〜４
のアルキル基、炭素数１〜４のアルコキシル基、ジアル
キルアミノ基又はニトロ基を表わ丁。〕
〔式中、Ａｒｓはナフタレン環、アントラセン環、スチ
リル基及びそれらの型換体あるいはピリジン環、７ラン
環、チオフェン環を表わし、職種はアルキル基又はベン
ジル基を表わす。〕
Ｒ１関
〔式中Ｓ Ｒｌａｌはアルキル基、ベンジル基、７エ二
ル基、ナフチル基を表わし、馬、。[In the formula, R11l represents a methyl group, an ethyl group, a 2-hydroxyethyl group, a 312-chloroethyl group, and % I'L
tts represents a methyl group, ethyl group, benzyl group, or phenyl group, and RIM represents hydrogen, chlorine, bromine, or a carbon number of 1 to 4.
represents an alkyl group, an alkoxyl group having 1 to 4 carbon atoms, a dialkylamino group or a nitro group. ] [In the formula, Ars represents a naphthalene ring, an anthracene ring, a styryl group, or a modified form thereof, a pyridine ring, a heptadane ring, or a thiophene ring, and the occupation type represents an alkyl group or a benzyl group. ] R1 [In the formula, S Rlal represents an alkyl group, a benzyl group, a 7-enyl group, or a naphthyl group;
は水素、炭素数１〜３のアルキル基、
炭素数１〜３のアルコキシ基、ジアルキルアミノ基、ジ
アラルキルアミノ基またはジアリールアミノ基を表わし
、ｎは１〜４の整数を表わし、認が２以上のときは）Ｌ
ｔｓｓは同じでも異なっていてもよい。represents hydrogen, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a dialkylamino group, a dialkylamino group, or a diarylamino group; n represents an integer of 1 to 4; ) L
tss may be the same or different.
Ｒ１？Ｉは水素またはメトキシ基を表わす。〕１’Ｌｔ
ｓｓ
〔式中、１４ｍ５は炭素数１〜１１のアルキル基１置換
もしくは無置換のフェニル基又は複素環基を表わし、ｌ
’Ｌｔ＊ｓ ｌ几廁はそれぞれ同一でも異なっていても
よく、水素、炭素数１〜４のアルキル基、ヒドロキシア
ルキル基、クロルアルキル基、置換又は無置換のアラル
キル基を表わすか、またはＲ１１ｌとｇａｓは互いに結
合し窒素を含む複素環を形成していてもよい。−！Ｓは
同一でも興なっていてもよく、水素、炭素数１〜４のア
ルキル基、アルコキシ基又はハロゲンを表わす。〕
１％ｍ
〔式中、ｌ’Ｌａｓは水素またはハロゲン原子を表わし
、人ｒ４は置換または無置換の７エ二ル基、ナフチル基
、アントリル基あるいはカルバゾリル基を表わす。〕
〔式中、−は水素、ハロゲン、シアノ基、炭素数１〜４
のアルコキシ基または炭素数１〜４のアルキル基を表わ
し％ ＡｒＢはを表わし％ Ｒ１４１は炭素数１〜４の
アルキル基を表わし、−は水素、ハロゲン、
炭素数１〜４のアルキル基、炭素数１〜４のアルコキシ
基またはジアルキルアミノ基を表わし、ｎは１または２
であって、ｎが２のときは−は同一でも異なって
もよく、−６および−６は水素、炭素数１〜４の置換ま
たは無置換のアルキル基あるいは置換または無置換のベ
ンジル基を表わす。〕
〔式中、−及びｎｍはカルバゾリル基、ピリジル基、チ
ェニル基、インドリル基、フリル基或いはそれぞれ置換
もしくは非置換のフェニル基、スチリル基、ナフチル基
またはアントリル基であって、これらの置換基がジアル
キルアミノ基、アルキル基、アルコキシ基、カルボキシ
基またけそのエステル、ハロゲン原子、シアノ基、アラ
ルキルアミノ基、Ｎ−アルキル−Ｎアラルキルアミノ基
、アミノ基、ニトロ基およびアセチルアミノ基からなる
群から選ばれた基を表わす。〕
〔式中、−は低級アルキル基またはベンジル基を表わし
、Ｒ□Ｓは水素原子１低級アルキル基、低級アルコキシ
基、ハロゲン原子、ニトロ基、アミノ基あるいは低級ア
ルキル基またはベンジル基で置換されたアミノ基を表わ
し、ｎは１または２の整数な表わ丁。〕
〔式中、Ｒｕｓは水素原子、アルキル基、アルコキシ基
またはハロゲン原子を表わし、Ｒ濡およびＲ３４ｓはア
ルキル基、置換または無置換のアラルキル基あるいは置
換または無置換のアリール基を表わし、ｎｕｓは水素原
子または置換もしくは無置換のフェニル基を表わし、ま
た、人ｒ−はフェニル基またはす７チル基を表わす０〕
〔式中、ｈはＯｌたは１の整数、ＲＭｓは水素原子、ア
ルキル基または置換もしくは無置換の７エール基を示し
、ＡＩは
９−アントリル基または置換もしくは無置換のＮ−アル
キルカルバゾリル基を表わし、ここで−鉱水素原子、ア
ルキル
基、アルコキク基、ハロゲン原子またはルキル基、置換
または無置換のアラルキル基、置換または無置換のアリ
ール基を示し、ＲｓｕおよびＲ１１１は環を形成しても
よい）を表わし、ｍは０，１．２または３の整数であっ
て、ｍが２以上のときはａｍは同一でも異なってもよい
。〕
〔式中、Ｒ４０１＋ Ｒ４１１およびＲ４２ｓは水素、
低級アルキル基、低級アルコキシ基、ジアルキルアミノ
基またはハロゲン原子を表わし、ｎは０またはｌを表わ
す。〕
一般式（Ｉ）で表わされる化合物には、たとえば９−エ
チルカルバゾール−３−アルデヒド、１−メチル−１−
フェニルヒドラゾン、９−エチルカルバソール−３−ア
ルデヒド１−ぺ／ジルー１−フェニルヒドラゾン、９−
エチルカルバゾール−３−アルデヒド１．１−ジフェニ
ルヒドラゾｙなどがある。R1? I represents hydrogen or a methoxy group. ]1'Lt
ss [In the formula, 14m5 represents a monosubstituted or unsubstituted alkyl group having 1 to 11 carbon atoms or a phenyl group or a heterocyclic group,
'Lt*sl几廁 may be the same or different, and each represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group, a chloroalkyl group, a substituted or unsubstituted aralkyl group, or R11l and The gases may be bonded to each other to form a nitrogen-containing heterocycle. -! S may be the same or different, and represents hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group, or a halogen. ] 1%m [In the formula, l'Las represents a hydrogen or halogen atom, and r4 represents a substituted or unsubstituted 7-enyl group, naphthyl group, anthryl group, or carbazolyl group. ] [In the formula, - is hydrogen, halogen, cyano group, carbon number 1-4
represents an alkoxy group or an alkyl group having 1 to 4 carbon atoms, % ArB represents an alkyl group having 1 to 4 carbon atoms, - represents hydrogen, halogen, an alkyl group having 1 to 4 carbon atoms, represents 1 to 4 alkoxy groups or dialkylamino groups, n is 1 or 2
When n is 2, - may be the same or different, and -6 and -6 represent hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted benzyl group. . [In the formula, - and nm are a carbazolyl group, pyridyl group, chenyl group, indolyl group, furyl group, or substituted or unsubstituted phenyl group, styryl group, naphthyl group or anthryl group, and these substituents are selected from the group consisting of dialkylamino group, alkyl group, alkoxy group, carboxy group or ester thereof, halogen atom, cyano group, aralkylamino group, N-alkyl-N aralkylamino group, amino group, nitro group and acetylamino group represents a group. [In the formula, - represents a lower alkyl group or a benzyl group, and R□S is a hydrogen atom substituted with a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group, or a lower alkyl group or a benzyl group. Represents an amino group, where n is an integer of 1 or 2. [In the formula, Rus represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, R and R34s represent an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, and nus represents hydrogen represents an atom or a substituted or unsubstituted phenyl group, and r- represents a phenyl group or a phenyl group. [In the formula, h is Ol or an integer of 1, RMs is a hydrogen atom, an alkyl group, or represents a substituted or unsubstituted 7-ale group, and AI represents a 9-anthryl group or a substituted or unsubstituted N-alkylcarbazolyl group, where - mineral hydrogen atom, alkyl group, alkoxylic group, halogen atom or alkyl represents a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, Rsu and R111 may form a ring), m is an integer of 0, 1.2 or 3, When m is 2 or more, am may be the same or different. ] [In the formula, R401+ R411 and R42s are hydrogen,
It represents a lower alkyl group, a lower alkoxy group, a dialkylamino group or a halogen atom, and n represents 0 or l. ] Compounds represented by general formula (I) include, for example, 9-ethylcarbazol-3-aldehyde, 1-methyl-1-
Phenylhydrazone, 9-ethylcarbasol-3-aldehyde 1-pe/ziru-1-phenylhydrazone, 9-
Examples include ethylcarbazole-3-aldehyde 1,1-diphenylhydrazoy.
一般式（２）で表わされる化合物には、たとえば４−ジ
エチルアミノスチレン−β−アルデヒド１−メＦ−ルー
１−フェニルヒドラゾン、４−／トキシナ７タレンー１
−アルデヒドｌ−ベンジル−１−フェニルヒドラゾンな
どがある。Examples of the compound represented by the general formula (2) include 4-diethylaminostyrene-β-aldehyde 1-meF-1-phenylhydrazone, 4-/toxina7talene-1
-Aldehyde l-benzyl-1-phenylhydrazone and the like.
一般式（３）で表わされる化合物にはたとえば、４−メ
トキシベンズアルデヒド１−メチル−１−フェニルヒド
ラゾン、２，４−ジメトキシベンズアルデヒド１−ベン
ジル−１−フェニルヒドラゾ／、４−ジエチルアミノベ
ンズアルデヒド１．１−ジフェニルヒドラゾン、４−メ
トキシベンズアルデヒド１−ベンジル−１−（４−メト
キシ）フェニルヒドラゾン、４−ジフェニルアミノベン
ズアルデヒド１−ベンジル−ｌ−フェニルヒドラゾン、
４−ジベンジルアミノベンズアルデヒド−１，１−ジフ
ェニルヒドラゾ／などがある。Examples of the compound represented by the general formula (3) include 4-methoxybenzaldehyde 1-methyl-1-phenylhydrazone, 2,4-dimethoxybenzaldehyde 1-benzyl-1-phenylhydrazo/, and 4-diethylaminobenzaldehyde 1.1 -diphenylhydrazone, 4-methoxybenzaldehyde 1-benzyl-1-(4-methoxy)phenylhydrazone, 4-diphenylaminobenzaldehyde 1-benzyl-l-phenylhydrazone,
Examples include 4-dibenzylaminobenzaldehyde-1,1-diphenylhydrazo/and the like.
一般式（４）で表わされる化合物には、たとえば１．１
−ビス（４−ジベンジルアミノフェニル）プロパン、ト
リス（４−ジエチルアミノフェニル）メタン、１．ｌ−
ビス（４−ジベンジルアミノフェニル）プロパン％ ２
１２’ −ジメチル−４，４′−ビス（ジエチルアミノ
）−トリフェニルメタンなどがある。The compound represented by general formula (4) includes, for example, 1.1
-bis(4-dibenzylaminophenyl)propane, tris(4-diethylaminophenyl)methane, 1. l-
Bis(4-dibenzylaminophenyl)propane% 2
Examples include 12'-dimethyl-4,4'-bis(diethylamino)-triphenylmethane.
一般式（５〕で表わされる化合物には、たとえば９−（
４−ジエチルアミノスチリル）アント２セン、９−ブロ
ム−ｔｏ−、（４−ジエチルアミノスチリル）アント２
センなどがある。The compound represented by the general formula (5) includes, for example, 9-(
4-diethylaminostyryl) anto 2cene, 9-bromo-to-, (4-diethylaminostyryl) anto 2
There are Sen, etc.
一般式（６）で表わされる化合物には、たとえば９−（
４−ジメチルアミノベンジリデン）フルオレン、３−（
９−フルオレノンデン）−９−エチルカルバゾールなど
がおる。The compound represented by general formula (6) includes, for example, 9-(
4-dimethylaminobenzylidene) fluorene, 3-(
Examples include 9-fluorenonedene)-9-ethylcarbazole.
一般式（７）で表わされる化合物には、たとえばｌ、２
−ビス（４−ジエチルアミノスチリル）ベンゼン、１，
２−ビス（２，４−ジメトキシスチリル）ベンゼンがあ
る。The compound represented by general formula (7) includes, for example, l, 2
-bis(4-diethylaminostyryl)benzene, 1,
2-bis(2,4-dimethoxystyryl)benzene.
一般式（８）で表わ嘔れろ化合物には、たとえば３−ス
チリル−９−エチルカルノ（ソール、３−（４−メトキ
シスチリル）−９−エチルカルノ（ゾールなどがある。Examples of the compound represented by the general formula (8) include 3-styryl-9-ethylcarno(sol) and 3-(4-methoxystyryl)-9-ethylcarno(sol).
一般式（９）で表わされる化合物には、たとえば４−ジ
フェニルアミノスチルベン、４−ジベンジルアミノステ
ルベン、４−ジＦリルアミノスチルペン、１−（４−ジ
フェニルアミノスチリル）ナフタレン、１−（４−ジエ
チルアミノスチリル）す７タレ／などがある。Examples of the compound represented by the general formula (9) include 4-diphenylaminostilbene, 4-dibenzylaminosterbene, 4-diFlylaminostilpene, 1-(4-diphenylaminostyryl)naphthalene, 1-(4-diphenylaminostilbene), -diethylaminostyryl)su7 sauce/etc.
一般式（イ）で表わされる化合物には、たとえば４’
−ジフェニルアミノ−α−フェニルスチルベン ４／
−、ｌチルフェニルアミノ−α−７二二ルスチルペンな
どがある。The compound represented by the general formula (a) includes, for example, 4'
-diphenylamino-α-phenylstilbene 4/
-, l-tylphenylamino-α-7-22-stilpene, and the like.
一般式圓で表わされる化合物には、たとえば１−フェニ
ル−３−（４−ジエチルアミノスチリル）−５−（４−
ジエチルアミノフェニル）ビ’） ソＩＪン、１−フェ
ニル−３−（４−ジエチルアミノスチリル）−５−（４
−ジエチルアミノフェニル）ピラゾリンなどがある。Examples of compounds represented by the general formula are 1-phenyl-3-(4-diethylaminostyryl)-5-(4-
diethylaminophenyl) bi') SOIJn, 1-phenyl-3-(4-diethylaminostyryl)-5-(4
-diethylaminophenyl)pyrazoline, etc.
この他の正孔搬送物質としては、たとえば２゜５−ビス
（４−ジエチルアミノフェニル）−１゜３．４−オキサ
ジアゾール、２，５−ビス〔４−（４−ジエチルアミノ
スチリル）フェニルツー１．３．４−オキサジアゾール
、２−（９−エチルカルバソリルー３−）−５−（４−
ジエチルアミノフェニル）−１，３，４−オキサジアゾ
ールなどのオキサジアゾール化合物、２−ビニル−４−
（２−クロルフェニル）−５−（４−ジエチルアミノフ
ェニル）オキサゾール、２−（４−ジエチルアミノフェ
ニル）−４−７二二ルオキサゾールなどのオキサゾール
化合物などの低分子化合物がある。また、ポリ−Ｎ−ビ
ニルカルバゾール、ノ１０ゲ／化ポリーＮ−ビニルカル
バゾール、ポリビニルピレン１ポリビニルアントラセン
、ピレンホルムアルデヒド樹脂、工ｆ Ａ／ 力＃バゾ
ールホルムアルデヒド樹脂ナトの高分子化合物も使用で
きる。Other hole transport substances include, for example, 2゜5-bis(4-diethylaminophenyl)-1゜3.4-oxadiazole, 2,5-bis[4-(4-diethylaminostyryl)phenyl-1 .3.4-Oxadiazole, 2-(9-ethylcarbasolyl-3-)-5-(4-
oxadiazole compounds such as (diethylaminophenyl)-1,3,4-oxadiazole, 2-vinyl-4-
There are low molecular weight compounds such as oxazole compounds such as (2-chlorophenyl)-5-(4-diethylaminophenyl)oxazole and 2-(4-diethylaminophenyl)-4-7dynyloxazole. Further, polymeric compounds such as poly-N-vinylcarbazole, polyvinylcarbazole, polyvinylpyrene-1-polyvinylanthracene, pyrene formaldehyde resin, and pyrene formaldehyde resin can also be used.
電荷搬送物質としては、たとえば、クロルアニル、ブロ
ムアニル、テトラシアノエチレン、テトラシアノキノン
ジメタン、２，４．７−）ジニトロ−９−フルオレノン
、２，４，５．７−ｆトラニトロ−９−フルオレノン、
２，４゜５．７−テトラニトロキサントン、２，４．８
−トリニドロチオキサントン、２，６．８−）リートロ
ー４Ｈ−インデノ（Ｉ，２−ｂ）チオフェン−４−オン
、１１３ ｙ ７− ）リニトロジベンゾチオ７エン−
５，５−ジオキサイドなどがある。Examples of the charge transport substance include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinone dimethane, 2,4,7-)dinitro-9-fluorenone, 2,4,5.7-ftranitro-9-fluorenone,
2,4゜5.7-tetranitroxanthone, 2,4.8
-Trinidrothioxanthone, 2,6.8-) Lietro 4H-indeno(I,2-b)thiophen-4-one, 113y7-)linitrodibenzothio7ene-
Examples include 5,5-dioxide.
これらの電荷搬送物質は単独又は２８１！以上混合して
用いられる。These charge transport substances can be used alone or 281! A mixture of the above is used.
なお、以上のようにして得られる感光体には、いずれも
導電性支持体と感光層の間に必要に応じて接着層又はバ
リヤ層を設けることができる。In any of the photoreceptors obtained as described above, an adhesive layer or a barrier layer may be provided between the conductive support and the photosensitive layer, if necessary.
これらの層に用いられる材料としてはポリアミド、ニト
ロセルロース、酸化アルミニウムなどが適当で、また膜
厚は１μ以下が好ましい。Suitable materials for these layers include polyamide, nitrocellulose, aluminum oxide, and the like, and the film thickness is preferably 1 μm or less.
第１図の感光体を作成するには、導電性支持体上にビス
アゾ顔料なＵ８Ｆ ３，９７３，９５９、ＵＳｐ３．９
９６，０４９等に記載されている真空蒸着方法で真空蒸
着するか、あるいは、ビスアゾ顔料の微粒子を必要とあ
れば結合剤を溶解した適当な溶剤中に分散し、これを導
電性支持体上に塗布乾燥し、更に必要とあれば、例えば
特開昭５１−９０８２７号公報に示されているようなパ
フ研摩等の方法により表面仕上をするか、膜厚を調整し
た後、電荷搬送物質及び結合剤を含む溶液を塗布乾燥し
て得られる。To make the photoreceptor of FIG. 1, the bisazo pigment U8F 3,973,959, USp 3.9
96,049, etc., or by dispersing bisazo pigment fine particles in a suitable solvent in which a binder is dissolved, if necessary, and depositing this on a conductive support. After coating and drying, if necessary, the surface is finished by a method such as puff polishing as shown in JP-A No. 51-90827, or after adjusting the film thickness, the charge transporting substance and the bond are applied. It is obtained by coating and drying a solution containing the agent.
第２図の感光体を作成するにはビスアゾ顔料の微粉末を
電荷搬送物質及び結合剤を溶解した溶液中に分散せしめ
、これを導電性支持体上に塗布乾燥すればよい。The photoreceptor shown in FIG. 2 can be prepared by dispersing a fine powder of bisazo pigment in a solution containing a charge transporting substance and a binder, and applying and drying this onto a conductive support.
いずれの場合も本発明に使用されるビスアゾ顔料はボー
ルミル等によ）粒径５μ以下、好ましくは２μ以下に粉
砕して用いられる。塗布方法は通常の手段、例えばドク
ターブレード、ディッピング、ワイヤーバーなどで行な
う。In either case, the bisazo pigment used in the present invention is ground (by ball mill or the like) to a particle size of 5 μm or less, preferably 2 μm or less. The coating method is carried out by conventional means such as doctor blade, dipping, wire bar, etc.
本発明の感光体を用いて複写を行なうには、感光層面に
帯電、露光を施した後、現像を行ない、必要によって、
紙などへ転写を行うことによル達成される。To perform copying using the photoreceptor of the present invention, the surface of the photoreceptor layer is charged and exposed, and then developed, and if necessary,
This is accomplished by transferring to paper, etc.
次に本発明を実施例によ）具体的に説明するが、これＫ
より本発明の実施の卵様が限定されるものではない。Next, the present invention will be specifically explained using examples.
The implementation of the present invention is not limited to egg-like forms.
実施例１
ビスアゾ顔料屋１２１を７６重量部、ポリエステル樹脂
（東洋紡績社製バイロン２００）のテトララヒドロフラ
ン溶液（固形分濃度２％）１２６０重量部、およびテト
ラヒドロ７ラン３７００重量部をボールミル中で粉砕混
合し、得られた分散液をアルミニウム蒸着したポリエス
テルベース（導電性支持体）のアルミ面上にドクターブ
レードを用いて塗布し、自然乾燥して、厚さ約１μｍの
電荷発生層を形成した。Example 1 76 parts by weight of Bisazo Pigment Ya 121, 1260 parts by weight of a tetrahydrofuran solution (solid content concentration 2%) of polyester resin (Vylon 200 manufactured by Toyobo Co., Ltd.), and 3700 parts by weight of Tetrahydro 7ran were mixed in a ball mill. After pulverization and mixing, the resulting dispersion was applied onto the aluminum surface of an aluminum-deposited polyester base (conductive support) using a doctor blade, and air-dried to form a charge generation layer with a thickness of approximately 1 μm. .
この電荷発生層上に、電荷搬送物質として９−エチルカ
ルバゾール−３−アルデヒドｌ−メチル−１−フェニル
ヒドラゾン２重量部、ポリカーボネート樹脂（今人社製
パンライ）Ｋ−１３００）２重量部およびテトラヒドロ
フラン１６重量部を混合溶解した溶液をドクターブレー
ドを用いて塗布し、８０Ｃで２分間、ついで１０５Ｃで
５分間乾燥して厚さ約２０μｍの電荷搬送層を形成して
、第１図に示した積層型の感光体Ａ１を作成した。On this charge generation layer, 2 parts by weight of 9-ethylcarbazole-3-aldehyde 1-methyl-1-phenylhydrazone, 2 parts by weight of polycarbonate resin (Panrye K-1300 manufactured by Konjinsha Co., Ltd.) and 16 parts by weight of tetrahydrofuran were applied as a charge transport substance. A solution in which parts by weight were mixed and dissolved was coated using a doctor blade, and dried at 80C for 2 minutes and then at 105C for 5 minutes to form a charge transport layer with a thickness of about 20 μm. A photoreceptor A1 was prepared.
実施例２〜Ｂ
実施例１で用いたビスアゾ顔料Ａ１２１の代りに後記表
−１に示すビスアゾ顔料を用いた以外は実施例１と同様
にして感光体屋２〜８を作成した。Examples 2 to B Photoreceptors 2 to 8 were prepared in the same manner as in Example 1, except that the bisazo pigment shown in Table 1 below was used instead of the bisazo pigment A121 used in Example 1.
実施例９〜２４
電荷搬送物質として１−フェニル−３−（４−ジエチル
アミノスチリル）−５−（４−ジエチルアミノフェニル
）ピラゾリンを用い、後記表−２に示すビスアゾ顔料を
用いた以外は実施例１と同様にして感光体Ａ９〜２４を
作成した０実施例２５〜３４
電荷搬送物質としてα−フェニル−４’−Ｎ。Examples 9 to 24 Example 1 except that 1-phenyl-3-(4-diethylaminostyryl)-5-(4-diethylaminophenyl)pyrazoline was used as the charge transport substance and the bisazo pigment shown in Table 2 below was used. Example 25-34 Photoreceptors A9-24 were prepared in the same manner as in Example 25-34 α-phenyl-4′-N was used as the charge transport substance.
Ｎ−ジフェニルアミノスチルベンを用い、後記表−３に
示すビスアゾ顔料を用いた以外は実施例１と同様にして
感光体屋２５〜３４ を作成した。Photoreceptors 25 to 34 were prepared in the same manner as in Example 1, except that N-diphenylaminostilbene was used and the bisazo pigment shown in Table 3 below was used.
実施例３５〜４０
電荷搬送物質として１，１−ビス（４−ジベンジルアミ
ノフェニル）プロパンを用い、後記表−４に示すビスア
ゾ顔料を用いた以外は、実施例１と同様にして感光体４
３５〜４０を作成したＯ
これらの感光体Ａ１〜４０について、静電複写紙試験装
置（（株）川口電機製作新製、８Ｐ４２８型）を用いて
、−６ＫＶのコロナ放電を２０秒間行なって負に帯電せ
しめた後、２０秒間暗所に放置し、その時の表面電位Ｖ
ｐｏ（Ｖ）を測定し、次いで、タングステンランプによ
ってその表面が照度４．５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Ｈになるまでの時間
（秒）を求め、露光量Ｅ’Ａ （ルックス・秒）を算出
した。その結果を表−１〜表−４に示した。Examples 35 to 40 Photoreceptor 4 was prepared in the same manner as in Example 1, except that 1,1-bis(4-dibenzylaminophenyl)propane was used as the charge transport substance and the bisazo pigment shown in Table 4 below was used.
For these photoreceptors A1 to A1 to A40, a negative After charging it to
po (V) is measured, then the surface is irradiated with light using a tungsten lamp at an illuminance of 4.5 lux, the time (seconds) until the surface potential reaches Vpo of H is determined, and the exposure The quantity E'A (lux seconds) was calculated. The results are shown in Tables 1 to 4.
表−１
表−２
表−３
表−４
効 果
前記衣−１〜４の結果からも明らかなように本発明の感
光体は前記一般式（Ｉ）のビスアゾ顔料を電荷発生物質
として用いたので、高感度となった。Table-1 Table-2 Table-3 Table-4 Effect As is clear from the results of Examples 1 to 4 above, the photoreceptor of the present invention uses the bisazo pigment of the general formula (I) as a charge generating substance. Therefore, the sensitivity was high.
さらに、本発明の感光体黒５および蔦２６をリニー社製
複写機すコビーＰ−５００型に装着して画像出しを１０
．０００回繰少返しだが、その結果、いずれの感光体も
複写プロセスの繰返しにより変化することなく、鮮明な
画像が得られた。これにより、本発明の感光体が耐久性
においても優れたものであることが理解できるであろう
。Furthermore, the photoconductor black 5 and the vine 26 of the present invention were installed in a copier Coby P-500 manufactured by Linney Co., Ltd., and images were produced for 10 minutes.
．． Although the copying process was repeated 000 times, as a result, neither photoreceptor was changed by the repetition of the copying process, and a clear image was obtained. From this, it can be understood that the photoreceptor of the present invention is also excellent in durability.
第１図および第２図は本発明の感光体の構成例を示す拡
大断面図である。
１１・・・導電性支持体 １３・・・ビスアゾ顔料１
５・・・電荷発生層 １７・・・電荷搬送層１９１
、１９２・・・感光層FIGS. 1 and 2 are enlarged sectional views showing an example of the structure of the photoreceptor of the present invention. 11... Conductive support 13... Bisazo pigment 1
5... Charge generation layer 17... Charge transport layer 191
, 192...photosensitive layer
Claims (1)
ってもよく、水素原子、ハロゲン原子、置換又は無置換
のアルキル基、置換又は無置換のアルコキシ基、置換又
は無置換のアリール基、ベンゾイル基、シアノ基、置換
アミノ基、ニトロ基、アセチル基、又はカルボキシル基
又はそのエステルを表わし、ｎは１〜４の整数を表わす
。） で示されるビスアゾ顔料を含有する層を形成せしめたこ
とを特徴とする電子写真用感光体。[Claims] 1. General formula (I) ▲ Numerical formula, chemical formula, table, etc. on the conductive support ▼ (However, A represents a coupler residue, R may be the same or different, and a hydrogen atom , halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, benzoyl group, cyano group, substituted amino group, nitro group, acetyl group, or carboxyl group or ester thereof (wherein n represents an integer of 1 to 4.) An electrophotographic photoreceptor comprising a layer containing a bisazo pigment represented by the following formula.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13932586A JPH0731406B2 (en) | 1986-06-17 | 1986-06-17 | Electrophotographic photoconductor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13932586A JPH0731406B2 (en) | 1986-06-17 | 1986-06-17 | Electrophotographic photoconductor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62296147A true JPS62296147A (en) | 1987-12-23 |
| JPH0731406B2 JPH0731406B2 (en) | 1995-04-10 |
Family
ID=15242681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13932586A Expired - Fee Related JPH0731406B2 (en) | 1986-06-17 | 1986-06-17 | Electrophotographic photoconductor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0731406B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004300422A (en) * | 2003-03-19 | 2004-10-28 | Ricoh Co Ltd | Azo compound, method for producing the same and material for photosensitive layer |
-
1986
- 1986-06-17 JP JP13932586A patent/JPH0731406B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004300422A (en) * | 2003-03-19 | 2004-10-28 | Ricoh Co Ltd | Azo compound, method for producing the same and material for photosensitive layer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0731406B2 (en) | 1995-04-10 |
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