JPH0220976B2 - - Google Patents
Info
- Publication number
- JPH0220976B2 JPH0220976B2 JP7237584A JP7237584A JPH0220976B2 JP H0220976 B2 JPH0220976 B2 JP H0220976B2 JP 7237584 A JP7237584 A JP 7237584A JP 7237584 A JP7237584 A JP 7237584A JP H0220976 B2 JPH0220976 B2 JP H0220976B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- photoreceptor
- carrier
- 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
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 88
- -1 azo compound Chemical class 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 72
- 150000001875 compounds Chemical class 0.000 description 42
- 239000010408 film Substances 0.000 description 19
- 230000035945 sensitivity Effects 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 17
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 239000004419 Panlite Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000004431 polycarbonate resin Substances 0.000 description 6
- 229920005668 polycarbonate resin Polymers 0.000 description 6
- 229920006267 polyester film Polymers 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052711 selenium Inorganic materials 0.000 description 5
- 239000011669 selenium Substances 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ZXBSSAFKXWFUMF-UHFFFAOYSA-N 1,2,3-trinitrofluoren-9-one Chemical compound C12=CC=CC=C2C(=O)C2=C1C=C([N+](=O)[O-])C([N+]([O-])=O)=C2[N+]([O-])=O ZXBSSAFKXWFUMF-UHFFFAOYSA-N 0.000 description 2
- 125000006012 2-chloroethoxy group Chemical group 0.000 description 2
- GMGDWNYWMLZUEF-UHFFFAOYSA-N 2-hydroxy-n-(4-methoxy-2-methylphenyl)-11h-benzo[a]carbazole-3-carboxamide Chemical compound CC1=CC(OC)=CC=C1NC(=O)C1=CC2=CC=C(C=3C(=CC=CC=3)N3)C3=C2C=C1O GMGDWNYWMLZUEF-UHFFFAOYSA-N 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 150000001716 carbazoles Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000113 methacrylic resin Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 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 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- JOERSAVCLPYNIZ-UHFFFAOYSA-N 2,4,5,7-tetranitrofluoren-9-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O JOERSAVCLPYNIZ-UHFFFAOYSA-N 0.000 description 1
- HDVGAFBXTXDYIB-UHFFFAOYSA-N 2,7-dinitrofluoren-9-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C2=C1 HDVGAFBXTXDYIB-UHFFFAOYSA-N 0.000 description 1
- RXGKQQXAEWMOGW-UHFFFAOYSA-N 2-[2-(4-octan-4-ylphenyl)ethenyl]-n,n-diphenylaniline Chemical compound C1=CC(C(CCC)CCCC)=CC=C1C=CC1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 RXGKQQXAEWMOGW-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- FUCBZYNPEREUJH-UHFFFAOYSA-N 2-methoxy-n,n-diphenylaniline Chemical compound COC1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 FUCBZYNPEREUJH-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- VOPISUYJMWWTCD-UHFFFAOYSA-N 9-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethenyl]carbazole Chemical compound C1=CC(OC)=CC=C1C=CC1=CC=C(N(C=2C=CC(OC)=CC=2)C=2C3=CC=CC=2)C3=C1 VOPISUYJMWWTCD-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229920005497 Acrypet® Polymers 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- JRFKUVDHIAAEOU-UHFFFAOYSA-N [F-].[F-].[F-].[F-].[F-].[F-].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+] Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+] JRFKUVDHIAAEOU-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 125000003705 anilinocarbonyl group Chemical group O=C([*])N([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 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 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical group CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- XIEZAENNAGFLLZ-UHFFFAOYSA-N n-(2,3-dihydroindol-1-yl)-1-(1-ethyl-9h-carbazol-4-yl)methanimine Chemical compound C12=CC=CC=C2NC2=C1C(C=NN1C3=CC=CC=C3CC1)=CC=C2CC XIEZAENNAGFLLZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 150000004866 oxadiazoles 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical group CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
（産業上の利用分野）
本発明は感光体に関し、詳しくは特定のアゾ化
合物を含有する感光層を有する新規な感光体に関
する。
（従来技術）
従来、電子写真感光体としては、セレン、酸化
亜鉛、硫化カドミウム、シリコン等の無機光導電
性化合物を主成分とする感光層を有する無機感光
体が広く用いられて来た。しかし、これらは感
度、熱安定性、耐湿性、耐久性等において必ずし
も満足し得るものではない。例えば、セレンは結
晶化すると感光体としての特性が劣化してしまう
ため、製造上も難しく、また熱や指紋等が原因と
なり結晶化し、感光体としての性能が劣化してし
まう。また硫化カドミウムでは耐湿性や耐久性、
酸化亜鉛でも耐久性等に問題がある。
これら無機感光体の持つ欠点を克服する目的で
様々な有機光導電性化合物を主成分とする感光層
を有する有機感光体の開発・研究が近年盛んに行
なわれている。例えば特公昭50−10496号公報に
はポリ−Ｎ−ビニルカルバゾールと２，４，７−
トリニトロ−９−フルオレノンを含有する感光層
を有する有機感光体の記載がある。しかしこの感
光体は、感度および耐久性において必ずしも満足
できるものではない。このような欠点を改良する
ためにキヤリア発生機能とキヤリア輸送機能とを
異なる物質に分担させ、より高性能の有機感光体
を開発する試みがなされている。このようないわ
ゆる機能分離型の感光体は、それぞれの材料を広
い範囲から選択することができ、任意の性能を有
する感光体を比較的容易に作成し得ることから多
くの研究がなされてきた。
このような機能分離型の感光体において、その
キヤリア発生物質として、数多くの化合物が提案
されている。無機化合物をキヤリア発生物質とし
て用いる例としては、例えば、特公昭43−16198
号公報に記載された無定形セレンがあり、これは
有機光導電性化合物と組み合わせて使用される
が、無定形セレンからなるキヤリア発生層は熱に
より結晶化して感光体としての特性が劣化してし
まうという欠点は改良されてはいない。
また有機染料や有機顔料をキヤリア発生物質と
して用いる感光体も数多く提案されている。例え
ば、アゾ化合物を感光層中に含有する感光体とし
て、特開昭54−22834号公報、特開昭55−73057号
公報、特開昭55−117151号公報、特開昭56−
46237号公報等がすでに公知である。しかし、こ
れらのアゾ化合物は感度、残留電位あるいは、繰
り返し使用時の安定性の特性において、必ずしも
満足し得るものではなく、またキヤリア輸送物質
の選択範囲も限定されるなど、電子写真プロセス
の幅広い要求を十分満足させるものではない。
さらに近年感光体の光源としてはArレーザー、
He−Neレーザー等の気体レーザーや半導体レー
ザーが使用され始めている。これらのレーザーは
その特徴として時系列でON／OFFが可能であ
り、インテリジエント複写機をはじめとする画像
処理機能を有する複写機やコンピユーターのアウ
トプツト用のプリンターの光源として特に有望視
されている。中でも半導体レーザーはその性質上
音響光学素子等の電気信号／光信号の変換素子が
不要であることや小型・軽量化が可能であること
などから注目を集めている。しかしこの半導体レ
ーザーは気体レーザーに比較して低出力であり、
また発振波長も長波長（約780nm以上）であるこ
とから従来の感光体では分光感度が短波長側によ
り過ぎており、このままでは半導体レーザーを光
源とする感光体としての使用は不可能である。
（発明の目的）
本発明の目的は熱および光に対して安定で、か
つキヤリア発生能に優れた特定のアゾ化合物を含
有する感光体を提供することにある。
本発明の他の目的は、高感度にしてかつ残留電
位が小さく、また繰り返し使用してもそれらの特
性が変化しない耐久性の優れた感光体を提供する
ことにある。
本発明の更に他の目的は、広範なキヤリア輸送
物質との組み合わせにおいても、有効にキヤリア
発生物質として作用し得るアゾ化合物を含有する
感光体を提供することにある。
本発明の更に他の目的は、半導体レーザー等の
長波長光源に対しても十分の実用感度を有する感
光体を提供することにある。
本願発明の更に他の目的は、明細書中の記載か
らあきらかになるであろう。
（発明の構成）
本発明者らは、以上の目的を達成すべく鋭意研
究を重ねた結果、下記一般式〔〕で示されるア
ゾ化合物が感光体の有効成分として働き得ること
を見出し、本発明を完成したものである。
一般式〔〕
上記式中、Y1及びY2は水素原子、ハロゲン原
子、シアノ基、ハイドロキシ基、アルキル基また
はアルコキシ基、ｍ及びｎは０乃至２の整数をそ
れぞれ表わし、ただしｍ及びｎが共に０あること
はない。
Ａは、
(Industrial Application Field) The present invention relates to a photoreceptor, and more particularly to a novel photoreceptor having a photosensitive layer containing a specific azo compound. (Prior Art) Conventionally, inorganic photoreceptors having a photosensitive layer containing an inorganic photoconductive compound such as selenium, zinc oxide, cadmium sulfide, or silicon as a main component have been widely used as electrophotographic photoreceptors. However, these are not necessarily satisfactory in terms of sensitivity, thermal stability, moisture resistance, durability, etc. For example, when selenium crystallizes, its properties as a photoreceptor deteriorate, making it difficult to manufacture.Also, selenium crystallizes due to heat, fingerprints, etc., and its performance as a photoreceptor deteriorates. Cadmium sulfide also has moisture resistance, durability,
Even zinc oxide has problems with durability, etc. In order to overcome these drawbacks of inorganic photoreceptors, research and development have been actively conducted in recent years on organic photoreceptors having photosensitive layers containing various organic photoconductive compounds as main components. For example, in Japanese Patent Publication No. 50-10496, poly-N-vinylcarbazole and 2,4,7-
There is a description of an organic photoreceptor having a photosensitive layer containing trinitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability. In order to improve these drawbacks, attempts have been made to develop organic photoreceptors with higher performance by assigning the carrier generation function and the carrier transport function to different substances. Many studies have been conducted on such so-called function-separated type photoreceptors because each material can be selected from a wide range and a photoreceptor having arbitrary performance can be produced relatively easily. Many compounds have been proposed as carrier generating substances for such functionally separated photoreceptors. Examples of using inorganic compounds as carrier generating substances include, for example, Japanese Patent Publication No. 43-16198.
There is an amorphous selenium described in the publication, which is used in combination with an organic photoconductive compound, but the carrier generation layer made of amorphous selenium crystallizes due to heat and its properties as a photoreceptor deteriorate. The shortcoming of storing it away has not been improved. Many photoreceptors have also been proposed that use organic dyes or organic pigments as carrier generating substances. For example, as a photoreceptor containing an azo compound in the photosensitive layer, JP-A-54-22834, JP-A-55-73057, JP-A-55-117151, JP-A-56-
Publication No. 46237 and the like are already known. However, these azo compounds do not necessarily satisfy the characteristics of sensitivity, residual potential, or stability during repeated use, and the range of carrier transport materials that can be selected is also limited. It does not fully satisfy. Furthermore, in recent years, Ar laser has been used as a light source for photoreceptors.
Gas lasers such as He-Ne lasers and semiconductor lasers are beginning to be used. A characteristic of these lasers is that they can be turned on and off in chronological order, making them particularly promising light sources for copying machines with image processing functions, including intelligent copying machines, and printers for computer output. Among these, semiconductor lasers are attracting attention because their nature does not require an electrical signal/optical signal conversion element such as an acousto-optic element, and because they can be made smaller and lighter. However, this semiconductor laser has a low output compared to a gas laser,
Furthermore, since the oscillation wavelength is long (approximately 780 nm or more), the spectral sensitivity of conventional photoreceptors is higher on the short wavelength side, and as it is, it is impossible to use them as photoreceptors using semiconductor lasers as light sources. (Object of the Invention) An object of the present invention is to provide a photoreceptor containing a specific azo compound that is stable to heat and light and has excellent carrier generation ability. Another object of the present invention is to provide a photoreceptor with high sensitivity, low residual potential, and excellent durability whose characteristics do not change even after repeated use. Still another object of the present invention is to provide a photoreceptor containing an azo compound that can effectively act as a carrier generating material even in combination with a wide variety of carrier transport materials. Still another object of the present invention is to provide a photoreceptor having sufficient practical sensitivity even to long wavelength light sources such as semiconductor lasers. Still other objects of the present invention will become apparent from the description in the specification. (Structure of the Invention) As a result of intensive research to achieve the above object, the present inventors discovered that an azo compound represented by the following general formula [] can act as an active ingredient of a photoreceptor, and the present invention This is the completed version. General formula [] In the above formula, Y 1 and Y 2 represent a hydrogen atom, a halogen atom, a cyano group, a hydroxy group, an alkyl group, or an alkoxy group, m and n each represent an integer from 0 to 2, provided that m and n are both 0. There isn't. A is
【式】【formula】
【式】 または【formula】 or
【式】であつて、
Ｑは、置換・未置換のカルバモイル基
（[Formula], Q is a substituted/unsubstituted carbamoyl group (
【式】）、置換・未置換のスルフアモイ ル基（[Formula]), substituted and unsubstituted sulfamoy group (
【式】）であつて、R4は水素原
子、炭素数１〜４の置換・未置換のアルキル基、
および置換・未置換のアラルキル基、置換・未置
換のフエニル基、R5は水素原子、炭素数１〜４
の置換・未置換のアルキル基、置換・未置換の芳
香族炭素環基（例えば、置換・未置換のフエニル
基、置換・未置換のナフチル基、置換・未置換の
アンスリル基等）、または置換・未置換の芳香族
複素環基（例えば置換・未置換のカルバゾリル
基、置換・未置換のジベンゾフリル基等）を表
す。
これらの基の置換基としては、例えば炭素数１
〜４の置換・未置換のアルキル基（例えばメチル
基、エチル基、イソプロピル基、３級ブチル基、
トリフルオロメチル基等）、置換・未置換のアラ
ルキル基（例えば、ベンジル基、フエネチル基
等）、ハロゲン原子（塩素原子、臭素原子、弗素
原子、沃素原子）、炭素数１〜４の置換・未置換
のアルコキシ基（例えばメトキシ基、エトキシ
基、イソプロポキシ基、３級ブトキシ基、２−ク
ロルエトキシ基等）、ヒドロキシ基、置換・未置
換のアリールオキシ基（例えば、ｐ−クロルフエ
ノキシ基、１−ナフトキシ基等）、アシルオキシ
基（例えば、アセチルオキシ基、ｐ−シアノベン
ゾイルオキシ基等）、カルボキシル基、そのエス
テル基（例えば、エトキシカルボニル基、ｍ−ブ
ロモフエノキシカルボニル基等）、カルバモイル
基（例えばアミノカルボニル基、３級ブチルアミ
ノカルボニル基、アニリノカルボニル基等）、ア
シル基（例えば、アセチル基、ｏ−ニトロベンゾ
イル基等）、スルホ基、スルフアモイル基（例え
ば、アミノスルホニル基、３級ブチルアミノスル
ホニル基、ｐ−トリルアミノスルホニル基等）、
アミノ基、アシルアミノ基（例えば、アセチルア
ミノ基、ベンゾイルアミノ基等）、スルホンアミ
ド基（例えば、メタンスルホンアミド基、ｐ−ト
ルエンスルホンアミド基等）、シアノ基、ニトロ
基等が挙げられるが、好ましくは炭素数１〜４の
置換・未置換のアルキル基（例えば、メチル基、
エチル基、イソプロピル基、ｎ−ブチル基、トリ
フルオロメチル基等）、ハロゲン原子（塩素原子、
臭素原子、弗素原子、沃素原子）、炭素数１〜４
の置換・未置換のアルコキシ基（例えば、メトキ
シ基、エトキシ基、３級ブトキシ基、２−クロル
エトキシ基等）シアノ基、ニトロ基である。
Ｚは、置換・未置換の芳香族炭素環、または置
換・未置換の芳香族複素環を形成するに必要な原
子群であつて、具体的には例えば置換・未置換の
ベンゼン環、置換・未置換のナフタレン環、置
換・未置換のインドール環、置換・未置換のカル
バゾール環等を形成する原子群を表す。
これらの環を形成する原子群の置換基として
は、例えばR4，R5の置換基として挙げたような
一連の置換基が列挙されるが、好ましくはハロゲ
ン原子（塩素原子、臭素原子、弗素原子、沃素原
子）、スルホ基、スルフアモイル基（（例えばアミ
ノスルホニル基、ｐ−トリルアミノスルホニル基
等）である。
R1は、水素原子、置換・未置換のアルキル基、
置換・未置換のアミノ基、カルボキシル基、その
エステル基、置換・未置換のカルバモイル基、シ
アノ基であり好ましくは水素原子、炭素数１〜４
の置換・未置換のアルキル基（例えば、メチル
基、エチル基、イソプロピル基、３級ブチル基、
トリフルオロメチル基等）、シアノ基である。
A′は置換・未置換のアリール基であり、好ま
しくは置換・未置換のフエニル基で、これらの基
の置換基としては、例えばR4，R5の置換基とし
て挙げたような一連の置換基が列挙されるが、好
ましくはハロゲン原子（塩素原子、臭素原子、弗
素原子、沃素原子）、炭素数１〜４の置換・未置
換のアルキル基（例えば、メチル基、エチル基、
イソプロピル基、３級ブチル基、トリフルオロメ
チル基等）、炭素数１〜４の置換・未置換のアル
コキシ基（例えば、メトキシ基、エトキシ基、イ
ソプロポキシ基、３級ブトキシ基、２−クロルエ
トキシ基）である。
R2およびR3は置換・未置換のアルキル基、置
換・未置換のアラルキル基、および置換・未置換
のアリール基を表すが、好ましくは炭素数１〜４
の置換・未置換のアルキル基（例えば、メチル
基、エチル基、イソプロピル基、３級ブチル基、
トリフルオロメチル基等）、置換・未置換のフエ
ニル基（例えば、フエニル基、ｐ−メトキシフエ
ニル基、ｎ−クロルフエニル基等）を表す。
本発明において使用される前記一般式〔〕で
表されるアゾ化合物中、感度および熱および光に
対する安定性において、特に好ましい化合物は以
下の一般式〔〕で示される構造を有するもので
ある。
一般式〔〕
（式中、Y1′，Y2′及びＡは一般式〔〕と同一
である。）
前記一般式［］で示される本発明に有用など
ビスアゾ化合物の具体例としては、例えば次の構
造を有するものが挙げられるが、これによつて本
発明のビスアゾ化合物が限定されるものではな
い。
一般式〔〕の構造を有するもの。
一般式〔〕
前記一般式［］で示される本発明に有用なビ
スアゾ化合物の具体例としては、例えば次の構造
を有するものが挙げられるが、これによつて本発
明のビスアゾ化合物が限定されるものではない。
一般式［］の構造を有するもの。
一般式［］
[Formula]), where R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms,
and a substituted/unsubstituted aralkyl group, a substituted/unsubstituted phenyl group, R 5 is a hydrogen atom, and has 1 to 4 carbon atoms.
Substituted/unsubstituted alkyl group, substituted/unsubstituted aromatic carbocyclic group (e.g., substituted/unsubstituted phenyl group, substituted/unsubstituted naphthyl group, substituted/unsubstituted anthryl group, etc.), or substituted - Represents an unsubstituted aromatic heterocyclic group (for example, a substituted/unsubstituted carbazolyl group, a substituted/unsubstituted dibenzofuryl group, etc.). Substituents for these groups include, for example, carbon atoms with 1
~4 substituted/unsubstituted alkyl groups (e.g. methyl group, ethyl group, isopropyl group, tertiary butyl group,
trifluoromethyl group, etc.), substituted/unsubstituted aralkyl groups (e.g., benzyl group, phenethyl group, etc.), halogen atoms (chlorine atom, bromine atom, fluorine atom, iodine atom), substituted/unsubstituted aralkyl groups with 1 to 4 carbon atoms. Substituted alkoxy groups (e.g., methoxy, ethoxy, isopropoxy, tertiary butoxy, 2-chloroethoxy, etc.), hydroxy groups, substituted/unsubstituted aryloxy groups (e.g., p-chlorophenoxy, 1- naphthoxy group, etc.), acyloxy group (e.g., acetyloxy group, p-cyanobenzoyloxy group, etc.), carboxyl group, its ester group (e.g., ethoxycarbonyl group, m-bromophenoxycarbonyl group, etc.), carbamoyl group ( For example, aminocarbonyl group, tertiary butylaminocarbonyl group, anilinocarbonyl group, etc.), acyl group (e.g. acetyl group, o-nitrobenzoyl group, etc.), sulfo group, sulfamoyl group (e.g. aminosulfonyl group, tertiary butyl group, etc.) aminosulfonyl group, p-tolylaminosulfonyl group, etc.),
Preferred examples include amino group, acylamino group (e.g., acetylamino group, benzoylamino group, etc.), sulfonamide group (e.g., methanesulfonamide group, p-toluenesulfonamide group, etc.), cyano group, nitro group, etc. is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms (e.g., methyl group,
ethyl group, isopropyl group, n-butyl group, trifluoromethyl group, etc.), halogen atom (chlorine atom,
Bromine atom, fluorine atom, iodine atom), carbon number 1-4
Substituted/unsubstituted alkoxy groups (eg, methoxy group, ethoxy group, tertiary butoxy group, 2-chloroethoxy group, etc.), cyano group, and nitro group. Z is an atomic group necessary to form a substituted/unsubstituted aromatic carbocycle or a substituted/unsubstituted aromatic heterocycle, and specifically, for example, a substituted/unsubstituted benzene ring, a substituted/unsubstituted aromatic heterocycle, etc. Represents a group of atoms forming an unsubstituted naphthalene ring, a substituted/unsubstituted indole ring, a substituted/unsubstituted carbazole ring, etc. Examples of substituents for the atomic group forming these rings include a series of substituents such as those listed as substituents for R 4 and R 5 , but halogen atoms (chlorine, bromine, fluorine, etc.) are preferred. R 1 is a hydrogen atom, a substituted or unsubstituted alkyl group,
Substituted/unsubstituted amino group, carboxyl group, ester group thereof, substituted/unsubstituted carbamoyl group, cyano group, preferably hydrogen atom, carbon number 1-4
Substituted/unsubstituted alkyl groups (e.g., methyl group, ethyl group, isopropyl group, tertiary butyl group,
trifluoromethyl group, etc.) and cyano group. A′ is a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted phenyl group, and examples of substituents for these groups include a series of substituents such as those listed as substituents for R 4 and R 5 . Although the groups are listed, preferably halogen atoms (chlorine atom, bromine atom, fluorine atom, iodine atom), substituted/unsubstituted alkyl groups having 1 to 4 carbon atoms (for example, methyl group, ethyl group,
isopropyl group, tertiary butyl group, trifluoromethyl group, etc.), substituted/unsubstituted alkoxy groups having 1 to 4 carbon atoms (e.g., methoxy group, ethoxy group, isopropoxy group, tertiary butoxy group, 2-chloroethoxy basis). R 2 and R 3 represent a substituted/unsubstituted alkyl group, a substituted/unsubstituted aralkyl group, and a substituted/unsubstituted aryl group, but preferably have 1 to 4 carbon atoms.
Substituted/unsubstituted alkyl groups (e.g., methyl group, ethyl group, isopropyl group, tertiary butyl group,
trifluoromethyl group, etc.), substituted/unsubstituted phenyl group (e.g., phenyl group, p-methoxyphenyl group, n-chlorophenyl group, etc.). Among the azo compounds represented by the general formula [] used in the present invention, particularly preferable compounds in terms of sensitivity and stability against heat and light are those having the structure shown by the following general formula []. General formula [] (In the formula, Y 1 ′, Y 2 ′ and A are the same as the general formula [].) Specific examples of the bisazo compound useful in the present invention represented by the above general formula [] include the following structure. However, the bisazo compound of the present invention is not limited thereto. Those having the structure of the general formula []. General formula [] Specific examples of the bisazo compound useful in the present invention represented by the general formula [ ] include those having the following structure, but the bisazo compound of the present invention is not limited thereto. Those having the structure of the general formula [ ]. General formula []
【表】【table】
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【表】 一般式［］の構造を有するもの 一般式［］ [Table] Items having the structure of general formula [] General formula []
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【表】 一般式［］の構造を有するもの 一般式［］ [Table] Items having the structure of general formula [] General formula []
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【表】【table】
【表】【table】
【表】 一般式［］の構造を有するもの 一般式［］ [Table] Items having the structure of general formula [] General formula []
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【表】 一般式［］の構造を有するもの 一般式［］ [Table] Items having the structure of general formula [] General formula []
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【表】【table】
【表】【table】
【表】 一般式［］の構造を有するもの 一般式［］ [Table] Items having the structure of general formula [] General formula []
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以上如きアゾ化合物は公知の方法により容易に
合成することができる。以下その具体例を示す。
合成例 １
すなわち、２，７−ジニトロフルオレノン１
（東京化成社製）に、ホスホネート体２（Journal
of American Chemical Society83，1733
（1961））を反応させ、ジニトロ体３とし、これを
塩化第一スズで還元して、ジアミノ体４とした。
（Journal of Chemical Society，870（1954）
このジアミノ体４ 23.3ｇ（0.1モル）を１
の濃塩酸と１の水との混合液に加え分散させ
13.8ｇ（0.2モル）の亜硝酸ナトリウムを水0.1
に溶かした溶液を氷冷下５℃で滴下し、滴下終了
後、反応液を濾過し、濾液に50％六フツ化リンア
ンモニウム水溶液１を加え、生ずる沈澱を濾取
し、水洗した後、充分乾燥した。得られた塩を
Ｎ，Ｎ−ジメチルホルムアミド（DMF）1.5に
溶解し、次ぎの反応に使用するテトラゾニウム塩
溶液とした。
次に、２−ヒドロキシ−３−（４−メトキシ−
２−メチルフエニルカルバモイル）−ベンゾ〔ａ〕
カルバゾール（ナフトールAS−SR，ヘキスト社
製）79.3ｇ（0.2モル）、トリエタノールアミン60
ｇを４のＮ，Ｎ−ジメチルホルムアミドに溶解
し、氷冷しながら上記により調製したテトラゾニ
ウム塩溶液を滴下し、更に２時間撹拌し反応させ
た。生じた結晶を濾取し、この結晶を５のＮ，
Ｎ−ジメチルホルムアミドで２回、５のアセト
ンで２回洗浄した後、乾燥して目的のビスアゾ化
合物Ｂ−(1)70.3ｇ（67％）を得た。融点300゜以
上、FD−MSスペクトルにてｍ／Ｚ＝1047にM+
のピークを示すこと、また元素分析でＣ＝74.27
％、Ｎ＝11.95％、Ｈ＝4.52％（計算値は、Ｃ＝
74.8％、Ｎ＝12.03％、Ｈ＝4.33％）を示すことか
ら目的の物質が合成されたことが理解される。
本発明の前記アゾ化合物は優れた光導電性を有
し、これを用いて感光体を製造する場合、導電性
支持体上に本発明のアゾ化合物を結着剤中に分散
した感光層を設けることにより製造することがで
きるが、本発明のアゾ化合物の持つ光導電性のう
ち、特に優れたキヤリア発生能を利用してキヤリ
ア発生物質として用い、これと組み合わせて有効
に作用し得るキヤリア輸送物質と共に用いること
により、いわゆる機能分離型の感光体を構成した
場合、特にすぐれた結果が得られる。前記機能分
離型感光体は分散性のものであつてもよいが、キ
ヤリア発生物質を含むキヤリア発生層とキヤリア
輸送物質を含むキヤリア輸送層を積層した積層型
感光体とすることがより好ましい。
また本発明で用いられるアゾ化合物は前記一般
式〔〕で表されるアゾ化合物の中から単独、あ
るいは２種以上の組み合わせで用いることがで
き、また他のアゾ化合物との組み合わせで使用し
てもよい。
感光体の機械的構成は種々の形態が知られてい
るが、本発明の感光体はそれらのいずれの形態を
もとり得る。
通常は、第１図〜第６図の形態である。第１図
および第３図では、導電性支持体１上に前述のア
ゾ化合物を主成分とするキヤリア発生層２と、キ
ヤリア輸送物質を主成分として含有するキヤリア
輸送層３との積層体より成る感光層４を設ける。
第２図および第４図に示すように、この感光層４
は導電性支持体上に設けた中間層５を介してもう
けてもよい。このように感光層４を二層構成とし
たときに最も優れた電子写真特性を有する感光体
が得られる。また本発明においては、第５図およ
び第６図に示すように、前記キヤリア発生物質７
をキヤリア輸送物質を主成分とする層６中に分散
せしめて成る感光層４を導電性支持体１上に直
接、あるいは中間層５を介して設けてもよい。
本発明のアゾ化合物をキヤリア発生物質として
用いた場合、これと組み合わせて用いられるキヤ
リア輸送物質としてはトリニトロフルオレノンあ
るいはテトラニトロフルオレノンなどの電子を輸
送しやすい電子受容性物質のほかポリーＮ−ビニ
ルカルバゾールに代表されるような複素環化合物
を側鎖に有する重合体、トリアゾール誘導体、オ
キサジアゾール誘導体、イミダゾール誘導体、ピ
ラゾリン誘導体、ポリアリールアルカン誘導体、
フエニレンジアミン誘導体、ヒドラゾン誘導体、
アミノ置換カルコン誘導体、トリアリールアミン
誘導体、カルバゾール誘導体、スチルベン誘導
体、フエノチアジン誘導体等の正孔を輸送しやす
い電子供与性物質が挙げられるが、本発明に用い
られるキヤリア輸送物質はこれらに限定されるも
のではない。
二層構成の感光層４を構成するキヤリア発生層
２は導電性支持体１、もしくはキヤリア輸送層３
上に直接、あるいは必要に応じて接着層もしくは
バリヤー層などの中間層を設けた上に例えば次の
方法によつて形成することができる。
Ｍ−１ アゾ化合物を適当な溶媒に溶解した溶液
を、あるいは必要に応じて結着剤を加え混合溶
解した溶液を塗布する方法。
Ｍ−２ アゾ化合物をボールミル、ホモミキサー
等によつて分散媒中で微細粒子とし、必要に応
じて結着剤を加え混合分散した分散液を塗布す
る方法。
キヤリア発生層の形成に使用される溶媒あるい
は分散媒としては、ｎ−ブチルアミン、ジエチル
アミン、エチレンジアミン、イソプロパノールア
ミン、トリエタノールアミン、トリエチレンジア
ミン、Ｎ，Ｎ−ジメチルホルムアミド、アセト
ン、メチルエチルケトン、シクロヘキサン、ベン
ゼン、トルエン、キシレン、クロロホルム、１，
２−ジクロロエタン、ジクロロメタン、テトラヒ
ドロフラン、ジオキサン、メタノール、エタノー
ル、イソプロパノール、酢酸エチル、酢酸ブチ
ル、ジメチルスルホキシド等が挙げられる。
キヤリア発生層あるいはキヤリア輸送層に結着
剤を用いる場合は任意のものを用いることができ
るが、疎水性でかつ誘電率が高く、電気絶縁性の
フイルム形成性高分子重合体を用いるのが好まし
い。このような高分子重合体としては、たとえば
次のものを挙げることができるが、これらに限定
されるものではない。
Ｐ−１ ポリカーボネート
Ｐ−２ ポリエステル
Ｐ−３ メタクリル樹脂
Ｐ−４ アクリル樹脂
Ｐ−５ ポリ塩化ビニル
Ｐ−６ ポリ塩化ビニリデン
Ｐ−７ ポリスチレン
Ｐ−８ ポリビニルアセテート
Ｐ−９ スチレン−ブタジエン共重合体
Ｐ−10 塩化ビニリデン−アクリロニトリル共重
合体
Ｐ−11 塩化ビニル−酢酸ビニル共重合体
Ｐ−12 塩化ビニル−酢酸ビニル−無水マレイン
酸共重合体
Ｐ−13 シリコン樹脂
Ｐ−14 シリコン−アルキツド樹脂
Ｐ−15 フエノール−ホルムアルデヒド樹脂
Ｐ−16 スチレン−アルキツド樹脂
Ｐ−17 ポリ−Ｎ−ビニルカルバゾール
Ｐ−18 ポリビニルブチラール
Ｐ−19 ポリビニルフオルマール
これらの結着剤は、単独であるいは２種以上の
混合物として用いることができる。
このようにして形成されるキヤリア発生層２の
厚さは、0.01μm〜20μmである。またキヤリア発
生層あるいは感光層が分散系の場合アゾ化合物の
粒径は5μm以下であることが好ましく、更に好ま
しくは1μm以下である。
本発明の感光体に用いられる導電性支持体とし
ては、合金を含めた金属板、金属ドラムまたは導
電性ポリマー、酸化インジウム等の導電性化合物
や合金を含めたアルミニウム、パラジウム、金等
の金属薄膜を塗布、蒸着あるいはラミネートして
導電性化を達成した紙、プラスチツクフイルム等
が挙げられる。接着剤あるいはバリヤー層などの
中間層としては、前記結着剤として用いられる高
分子重合体のほか、ポリビニルアルコール、エチ
ルセルロース、カルボキシメチルセルロースなど
の有機高分子物質または酸化アルミニウムなどが
用いられる。
本発明の感光体は以上のような構成であつて、
後述する実施例からも明らかなように、帯電特
性、感度特性、画像形成特性に優れており、特に
繰り返し使用したときにも疲労劣化が少なく、耐
久性が優れたものである。
以下、本発明の実施例で具体的に説明するが、
これにより本発明の実施態様が限定されるもので
はない。
（実施例）
実施例 １
例示化合物Ｂ−(7)２ｇとポリカーボネート樹脂
「パンライトＬ−1250」（帝人化成社製）２ｇとを
１，２−ジクロロエタン110mlに加え、ボールミ
ルで12時間分散した。この分散液をアルミニウム
を蒸着したポリエステルフイルム上に、乾燥後の
膜厚が1μmになるように塗布し、キヤリア発生層
とし、更にその上に、キヤリア輸送層として、１
−（１−フエニル−４−カルバゾリル）メチリデ
ンアミノ−１，２，３，４−テトラヒドロキノリ
ン（下記構造式Ｋ−(1)）６ｇポリカーボネート樹
脂「パンライトＬ−1250」10ｇとを１，２−ジク
ロロエタン110mlに溶解した液を乾燥後の膜厚が
15μmになるように塗布して、キヤリア輸送層を
形成し、本発明の感光体を作成した。
以上のようにして得られた感光体を(株)川口電機
製作所SP−428型静電紙試験機を用いて、以下の
特性評価を行つた。帯電圧−6KVで５秒間帯電
した後、５秒間暗放置し、次いで感光体表面での
照度が35luxになるようにハロゲンランプ光を照
射して、表面電位を半分に減衰させるのに要する
露光量（半減露光量）Ｅ1/2を求めた。また
30lux・secの露光量で露光した後の表面電位（残
留電位）VRを求めた。さらに同様の測定を100回
繰に返して行つた。結果は第１表に示す通りであ
つた。 The above azo compounds can be easily synthesized by known methods. A specific example will be shown below. Synthesis example 1 That is, 2,7-dinitrofluorenone 1
(manufactured by Tokyo Kasei Co., Ltd.), phosphonate 2 (Journal
of American Chemical Society 83 , 1733
(1961)) to give the dinitro compound 3 , which was reduced with stannous chloride to give the diamino compound 4 .
(Journal of Chemical Society, 870 (1954) 23.3 g (0.1 mol) of this diamino compound 4 was
Add to a mixture of concentrated hydrochloric acid (1) and water (1) and disperse.
13.8g (0.2mol) of sodium nitrite in 0.1g of water
After dropping the solution dissolved in water at 5°C under ice-cooling, filter the reaction solution, add 1 part of a 50% phosphorous ammonium hexafluoride aqueous solution to the filtrate, collect the resulting precipitate by filtration, wash with water, and thoroughly dissolve. Dry. The obtained salt was dissolved in 1.5 ml of N,N-dimethylformamide (DMF) to prepare a tetrazonium salt solution to be used in the next reaction. Next, 2-hydroxy-3-(4-methoxy-
2-methylphenylcarbamoyl)-benzo[a]
Carbazole (naphthol AS-SR, manufactured by Hoechst) 79.3g (0.2mol), triethanolamine 60
g was dissolved in 4 N,N-dimethylformamide, and the tetrazonium salt solution prepared above was added dropwise while cooling with ice, and the mixture was further stirred for 2 hours to react. The resulting crystals were collected by filtration and treated with 5N,
After washing twice with N-dimethylformamide and twice with acetone (5), it was dried to obtain 70.3 g (67%) of the target bisazo compound B-(1). Melting point over 300°, M + at m/Z = 1047 in FD-MS spectrum
C=74.27 in elemental analysis.
%, N=11.95%, H=4.52% (calculated values are C=
74.8%, N=12.03%, H=4.33%), it is understood that the target substance was synthesized. The azo compound of the present invention has excellent photoconductivity, and when a photoreceptor is manufactured using the azo compound, a photosensitive layer in which the azo compound of the present invention is dispersed in a binder is provided on a conductive support. Among the photoconductivity possessed by the azo compound of the present invention, it can be used as a carrier-generating substance by taking advantage of its particularly excellent carrier-generating ability, and a carrier-transporting substance that can effectively act in combination with this. Particularly excellent results can be obtained when used together to form a so-called functionally separated photoreceptor. The functionally separated photoreceptor may be a dispersion type photoreceptor, but it is more preferably a laminated type photoreceptor in which a carrier generation layer containing a carrier generation substance and a carrier transport layer containing a carrier transport substance are laminated. Further, the azo compound used in the present invention can be used alone or in combination of two or more of the azo compounds represented by the above general formula [], and can also be used in combination with other azo compounds. good. Various types of mechanical configurations of photoreceptors are known, and the photoreceptor of the present invention can take any of these forms. Usually, the configuration is as shown in FIGS. 1 to 6. In FIG. 1 and FIG. 3, a laminate is formed of a carrier generation layer 2 containing the above-mentioned azo compound as a main component and a carrier transport layer 3 containing a carrier transport substance as a main component on a conductive support 1. A photosensitive layer 4 is provided.
As shown in FIGS. 2 and 4, this photosensitive layer 4
may be provided via an intermediate layer 5 provided on the conductive support. When the photosensitive layer 4 has a two-layer structure in this manner, a photoreceptor having the most excellent electrophotographic properties can be obtained. Further, in the present invention, as shown in FIGS. 5 and 6, the carrier generating substance 7
A photosensitive layer 4 comprising a carrier transport material dispersed in a layer 6 containing a carrier transport substance as a main component may be provided directly on the conductive support 1 or via an intermediate layer 5. When the azo compound of the present invention is used as a carrier generating substance, carrier transporting substances used in combination with the azo compound include electron-accepting substances that easily transport electrons such as trinitrofluorenone or tetranitrofluorenone, as well as polyN-vinylcarbazole. Polymers having a heterocyclic compound in the side chain as represented by, triazole derivatives, oxadiazole derivatives, imidazole derivatives, pyrazoline derivatives, polyarylalkane derivatives,
Phenylene diamine derivatives, hydrazone derivatives,
Examples include electron-donating substances that easily transport holes, such as amino-substituted chalcone derivatives, triarylamine derivatives, carbazole derivatives, stilbene derivatives, and phenothiazine derivatives, but the carrier transport substance used in the present invention is limited to these. isn't it. The carrier generation layer 2 constituting the photosensitive layer 4 having a two-layer structure is the conductive support 1 or the carrier transport layer 3.
It can be formed directly thereon or, if necessary, with an intermediate layer such as an adhesive layer or a barrier layer provided thereon, for example, by the following method. M-1 A method of applying a solution in which an azo compound is dissolved in a suitable solvent, or a solution in which a binder is added and mixed as necessary. M-2 A method in which an azo compound is made into fine particles in a dispersion medium using a ball mill, a homomixer, etc., and a binder is added if necessary to mix and disperse the resulting dispersion. Solvents or dispersion media used to form the carrier generation layer include n-butylamine, diethylamine, ethylenediamine, isopropanolamine, triethanolamine, triethylenediamine, N,N-dimethylformamide, acetone, methyl ethyl ketone, cyclohexane, benzene, and toluene. , xylene, chloroform, 1,
Examples include 2-dichloroethane, dichloromethane, tetrahydrofuran, dioxane, methanol, ethanol, isopropanol, ethyl acetate, butyl acetate, dimethyl sulfoxide, and the like. When using a binder in the carrier generation layer or carrier transport layer, any binder can be used, but it is preferable to use a film-forming polymer that is hydrophobic, has a high dielectric constant, and is electrically insulating. . Examples of such high molecular weight polymers include, but are not limited to, the following. P-1 Polycarbonate P-2 Polyester P-3 Methacrylic resin P-4 Acrylic resin P-5 Polyvinyl chloride P-6 Polyvinylidene chloride P-7 Polystyrene P-8 Polyvinyl acetate P-9 Styrene-butadiene copolymer P- 10 Vinylidene chloride-acrylonitrile copolymer P-11 Vinyl chloride-vinyl acetate copolymer P-12 Vinyl chloride-vinyl acetate-maleic anhydride copolymer P-13 Silicone resin P-14 Silicone-alkyd resin P-15 Phenol -Formaldehyde resin P-16 Styrene-alkyd resin P-17 Poly-N-vinylcarbazole P-18 Polyvinyl butyral P-19 Polyvinyl formal These binders can be used alone or as a mixture of two or more. can. The thickness of the carrier generation layer 2 thus formed is 0.01 μm to 20 μm. Further, when the carrier generation layer or the photosensitive layer is a dispersed type, the particle size of the azo compound is preferably 5 μm or less, more preferably 1 μm or less. The conductive support used in the photoreceptor of the present invention includes a metal plate including an alloy, a metal drum, a conductive polymer, a conductive compound such as indium oxide, and a metal thin film of aluminum, palladium, gold, etc. including an alloy. Examples include paper, plastic film, etc. that have been made conductive by coating, vapor depositing, or laminating. As an intermediate layer such as an adhesive or a barrier layer, in addition to the polymer used as the binder, an organic polymer material such as polyvinyl alcohol, ethyl cellulose, carboxymethyl cellulose, or aluminum oxide is used. The photoreceptor of the present invention has the above structure,
As is clear from the Examples described below, it has excellent charging characteristics, sensitivity characteristics, and image forming characteristics, and especially shows little fatigue deterioration even after repeated use, and is excellent in durability. Hereinafter, the present invention will be specifically explained in Examples,
This does not limit the embodiments of the present invention. (Examples) Example 1 2 g of Exemplified Compound B-(7) and 2 g of polycarbonate resin "Panlite L-1250" (manufactured by Teijin Chemicals) were added to 110 ml of 1,2-dichloroethane, and dispersed in a ball mill for 12 hours. This dispersion was applied onto a polyester film on which aluminum had been vapor-deposited so that the film thickness after drying would be 1 μm to form a carrier generation layer.
-(1-phenyl-4-carbazolyl)methylideneamino-1,2,3,4-tetrahydroquinoline (Structural formula K-(1) below) 6g polycarbonate resin "Panlite L-1250" 10g and 1,2-dichloroethane The film thickness after drying the solution dissolved in 110ml is
A carrier transport layer was formed by coating to a thickness of 15 μm, and a photoreceptor of the present invention was prepared. The photoreceptor obtained as described above was subjected to the following characteristic evaluation using an electrostatic paper tester SP-428 manufactured by Kawaguchi Electric Seisakusho Co., Ltd. After charging with a charging voltage of -6KV for 5 seconds, leave in the dark for 5 seconds, then irradiate with halogen lamp light so that the illuminance on the photoreceptor surface is 35 lux, and calculate the amount of exposure required to attenuate the surface potential by half. (Half-reduced exposure amount) E1/2 was determined. Also
The surface potential (residual potential) V R after exposure with an exposure amount of 30 lux·sec was determined. Furthermore, similar measurements were repeated 100 times. The results were as shown in Table 1.
【表】
比較例 １
キヤリア発生物質として下記ビスアゾ化合物Ｇ
−(1)を用いた他は、実施例１と同様にして比較用
感光体を作成した。
この比較用感光体について、実施例１と同様に
して測定を行つたところ、第２表に示す結果を得
た。[Table] Comparative Example 1 The following bisazo compound G was used as a carrier generating substance.
A comparative photoreceptor was prepared in the same manner as in Example 1 except that -(1) was used. When this comparative photoreceptor was measured in the same manner as in Example 1, the results shown in Table 2 were obtained.
【表】
以上の結果から明らかなように、本発明の感光
体は、比較用感光体に比べ、感度、残留電位およ
び繰り返しの安定性において極めて優れたもので
ある。
実施例 ２−４
キヤリア発生物質として例示化合物Ｂ−（15）、
Ｂ−（17）、およびＢ−（18）を用い、キヤリア輸
送物質として、それぞれ、４−メトキシ−4′−
（４−メトキシ）スチリル−トリフエニルアミン
（下記化合物Ｋ−(2)）、４−メトキシ−4′−（４−
メチル）スチリル−トリフエニルアミン（下記化
合物Ｋ−(3)）、および４−メトキシ−4′−スチリ
ル−トリフエニルアミン（下記化合物Ｋ−(4)）を
用い、他は実施例１と同様にして、本発明の感光
体を作成し、同様の測定を行なつたところ第３表
に示す結果を得た。
[Table] As is clear from the above results, the photoreceptor of the present invention is extremely superior in sensitivity, residual potential, and repetition stability compared to the comparative photoreceptor. Example 2-4 Exemplified compound B-(15) as a carrier generating substance,
B-(17) and B-(18) were used as carrier transport substances, respectively, and 4-methoxy-4'-
(4-methoxy)styryl-triphenylamine (compound K-(2) below), 4-methoxy-4'-(4-
methyl)styryl-triphenylamine (compound K-(3) below) and 4-methoxy-4'-styryl-triphenylamine (compound K-(4) below), and otherwise in the same manner as in Example 1. Then, a photoreceptor of the present invention was prepared and the same measurements were carried out, and the results shown in Table 3 were obtained.
【表】
実施例 ５
ポリエステルフイルム上にアルミニウム箔をラ
ミネートして成る導電性支持体上に、塩化ビニル
−酢酸ビニル−無水マレイン酸共重合体「エスレ
ツクMP−10」（積水化学社製）より成る厚さ
0.05μmの中間層を設け、その上に例示化合物Ｂ
−（32）２ｇを１，２−ジクロロエタン110mlに混
合し、ボールミルで24時間分散した分散液を乾燥
後の膜
厚が0.5μmになるようにして塗布、キヤリア発生
層を形成した。このキヤリア発生層の上に、４−
メチル−4′−スチリル−トリフエニルアミン（Ｋ
−(5)）６ｇとメタクリル樹脂「アクリペツト」
（三菱レイヨン社製）10ｇとを１，２−ジクロロ
エタン70mlに溶解した液を、乾燥後の膜厚が
10μmになるように塗布してキヤリア輸送層を形
成し、本発明の感光体を作成した。
この感光体について実施例１と同様の測定を行
なつたところ第１回目についてＥ1/2＝1.0lux・
sec、VR＝0Vの結果を得た。
実施例 ６
実施例５で用いた中間層を設けた導電性支持体
上に、例示化合物Ｂ−（65）の１％エチレンジア
ミン溶液を乾燥後の膜厚が0.3μmになるように塗
布し、キヤリア発生層を形成した。
次いでその上に、１−〔４−（Ｎ，Ｎ−ジエチル
アミノ）ベンジリデン〕−アミノ−１，２，３，
４−テトラヒドロキノリン（下記化合物Ｋ−(6)
６ｇとポリエステル樹脂「バイロン200」（東洋紡
績社製）10ｇとを１，２−ジクロロエタン70mlに
溶解し、この溶液を乾燥後の膜厚が12μmになる
ように塗布してキヤリア輸送層を形成し、本発明
の感光体を作成した。
この感光体について実施例１と同様の測定を行
つたところ第４表に示す結果を得た。
比較例 ２
実施例６において例示化合物Ｂ−（65）を下記
の構造式で表されるビスアゾ化合物Ｇ−(2)に代え
た他は同様にして比較用の電子写真感光体を作成
した。
この感光体について実施例１と同様の測定を行
つたその結果を第４表に示す。
[Table] Example 5 A vinyl chloride-vinyl acetate-maleic anhydride copolymer "Eslec MP-10" (manufactured by Sekisui Chemical Co., Ltd.) was placed on a conductive support consisting of a polyester film laminated with aluminum foil. thickness
A 0.05 μm intermediate layer is provided, and exemplified compound B is placed on top of the intermediate layer.
- (32) 2g was mixed with 110ml of 1,2-dichloroethane, and the dispersion was dispersed in a ball mill for 24 hours. After drying, the film was The coating was applied to a thickness of 0.5 μm to form a carrier generation layer. On top of this carrier generation layer, 4-
Methyl-4'-styryl-triphenylamine (K
-(5)) 6g and methacrylic resin "Acrypet"
(manufactured by Mitsubishi Rayon Co., Ltd.) and dissolved in 70 ml of 1,2-dichloroethane, the film thickness after drying was
A carrier transport layer was formed by coating to a thickness of 10 μm, and a photoreceptor of the present invention was prepared. The same measurements as in Example 1 were performed on this photoreceptor, and the first measurement was E1/2 = 1.0 lux.
sec, the result of V R =0V was obtained. Example 6 On the conductive support provided with the intermediate layer used in Example 5, a 1% ethylenediamine solution of Exemplary Compound B-(65) was applied to a dry film thickness of 0.3 μm, and a carrier was applied. A generation layer was formed. Then 1-[4-(N,N-diethylamino)benzylidene]-amino-1,2,3,
4-tetrahydroquinoline (compound K-(6) below) 6 g and 10 g of polyester resin "Vylon 200" (manufactured by Toyobo Co., Ltd.) were dissolved in 70 ml of 1,2-dichloroethane, and this solution was applied to a dry film thickness of 12 μm to form a carrier transport layer. , a photoreceptor of the present invention was prepared. The same measurements as in Example 1 were performed on this photoreceptor, and the results shown in Table 4 were obtained. Comparative Example 2 A comparative electrophotographic photoreceptor was prepared in the same manner as in Example 6 except that exemplified compound B-(65) was replaced with bisazo compound G-(2) represented by the following structural formula. The same measurements as in Example 1 were performed on this photoreceptor, and the results are shown in Table 4.
【表】
実施例 ７
実施例５において例示化合物Ｂ−（32）を例示
化合物Ｂ−（36）に代えた他は同様にしてキヤリ
ア発生層を形成した。この上に１−（１−エチル
−４−カルバゾリル）メチリデンアミノ−インド
リン（化合物Ｋ−(7)）６ｇとポリカーボネート
「パンライトＬ−1250」（帝人化成社製）10ｇと
を、１，２−ジクロロエタン70mlに溶解した液を
乾燥後の膜厚が10μmになるように塗布してキヤ
リア輸
送層を形成し、本発明の感光体を作成した。
この感光体について、実施例１と同様にして測
定を行つたところＥ1/2＝1.3lux・secおよびVR＝
0Vであつた。
実施例 ８
直径100mmのアルミニウム製ドラムの表面に塩
化ビニル−酢酸ビニル−無水マレイン酸共重合体
「エスレツクMP−10」（積水化学社製）より成る
厚さ0.05μmの中間層を設け、その上に例示化合
物Ｂ−（26）４ｇを１，２−ジクロロエタン400ml
に混合し、ボールミル分散機で24時間分散した分
散液を乾燥後の膜厚が0.6μmになるようにして塗
布し、キヤリア発生層を形成した。
さらにこの上に、４，4′−ジメチル−4″−（４
−メトキシ）スチリル−トリフエニルアミン（下
記化合物Ｋ−(8)）30ｇとポリカーボネート樹脂
「コーピロンＳ−1000」（三菱ガス化学社製）50ｇ
とを１，２−ジクロロエタン
400mlに溶解し、乾燥後の膜厚が13μmになるよう
に塗布してキヤリア輸送層を形成し、ドラム状の
感光体を作成した。
このようにして作成した感光体を電子写真複写
機「Ｕ−Bix1600MR」（小西六写真工業社製）の
改造機に装着し、画像を複写したところコントラ
ストが高く、原画に忠実でかつ鮮明な複写画像を
得た。また、これは10，000回繰り返しても変わ
ることはなかつた。
比較例 ３
実施例８において例示化合物Ｂ−（26）を下記
の構造式で表されるビスアゾ化合物（Ｇ−(3)）に
代えた他は、実施例８と同様にしてドラム状の比
較用感光体を作成し、実施例８と同様にして複写
画像を評価したところ、カブリが多い画像しか得
られなつた。また、複写を繰り返していくに従
い、複写画像のコントラストが低下し、2000回繰
り返すと、ほとんど複写画像は得られなかつた。
実施例 ９
ポリエステルフイルム上にアルミニウム箔をラ
ミネートして成る導電性支持体上に、塩化ビニル
−酢酸ビニル−無水マレイン酸共重合体「エスレ
ツクMF−10」（積水化学社製）より成る厚さ
0.05μmの中間層を設け、その上に例示化合物Ｂ
−（74）５ｇとポリカーボネート樹脂「パンライ
トＬ−1250」（帝人化成社製）3.3ｇとをジクロロ
メタン100mlに加え、ボールミルで24時間分散と
た分散液を乾燥時の膜厚が10μmになるように塗
布し、感光体を作成した。
以上のようにして得られた感光体を帯電圧を＋
6KVに代えた他は実施例１と同様にしてＥ1/2と
VRを測定した。１回目の結果はＥ1/2＝2.0lux・
secおよびVR＝0Vであつた。
実施例 10
アルミニウムを蒸着したポリエステルフイルム
上にキヤリア輸送層として、１−フエニル−３−
（ｐ−ジエチルアミノスチリル）−５−（ｐ−ジエ
チルアミノフエニル）ピラゾリン）下記化合物Ｋ
−(9)６ｇとポリエステル樹脂「バイロン200」
（東洋紡績社製）10ｇとを１，２−ジクロロエタ
ン70mlに溶解し、この溶液を乾燥後の膜厚が
10μmになるように塗布した。
次に、この上に例示化合物Ｂ−(9)１ｇとＢ−(10)
１ｇとを１，２−ジクロロエタン110mlに混合し、
ボールミルで24時間分散した分散液を乾燥後の膜
厚が0.5μmになるように塗布しキヤリア発生層と
し、本発明の感光体を形成した。
このようにして得られた感光体を実施例９と同
様にして評価したところＥ1/2＝1.7lux・secおよ
びVR＝＋5Vであつた。
実施例 11
ポリエステルフイルム上にアルミニウム箔をラ
ミネートして成る導電性支持体上に、塩化ビニル
−酢酸ビニル−無水マレイン酸共重合体「エスレ
ツクMF−10」（積水化学社製）より成る厚さ
0.05μmの中間層を設け、その上に例示化合物Ｂ
−（54）４ｇと４−メトキシ−4′−メチル−4″−
（４−メチル）スチリル−トリフエニルアミン
（下記化合物Ｋ−(10)８ｇとポリカーボネート樹脂
「パンライトＬ−1250」（帝人化成社製）３ｇと
をジクロロエタン100mlに加え、サンドグライン
ダーで24時間分散した分散液を乾燥時の膜厚が
10μmになるように塗布し、感光体を作成した。
以上のようにして得られた感光体を帯電圧を＋
6KVに代えた他は実施例１と同様にしてＥ1/2と
VRを測定した。１回目の結果はＥ1/2＝1.0lux・
secおよびVR＝0Vであつた。
実施例 12
例示化合物Ｂ−（66）の２％エチレンジアミン
溶液を、アルミニウムをラミネートしたポリエス
テルフイルム上に乾燥後の膜厚が0.5μmになるよ
うに塗布し、キヤリア発生層を形成した。さらに
その上にキヤリア輸送層として、４−メトキシ−
4′−（４−クロル）−スチリル−トリフエニルアミ
ン（下記化合物Ｋ−(11)）、４，4′−ジメチル−
4″−（４−ブロム）−スチリル−トリフエニルアミ
ン（下記化合物Ｋ−(12)）、または、４−（４−オク
チル）−スチリル−トリフエニルアミン（下記化
合物Ｋ−（13））を別々にそれぞれ約10ｇとポリカ
ーボネート
樹脂（帝人化成社製、パンライトＬ−1250）14ｇ
を１，２−ジクロロエタン140mlに溶解した溶液
を、乾燥時の膜厚が12μmとなるように塗布し乾
燥し、それぞれ３種のキヤリア輸送物質の異なる
感光体を得た。
この３種の感光体を、それぞれ川口電機製作所
(株)製SP−428型静電紙試験機を用いて、以下の特
性評価を行なつた。帯電圧−6KVで５秒間帯電
し、これを５秒間暗放置した後、ハロゲン光を資
料面照度が35luxになるように照射し、表面電位
を半分に減衰させるのに必要な露光量（半減露光
量、Ｅ1/2）を測定した。また、30lux・secの露
光量で露光した後の表面電位（残留電位）VRを
測定した。結果は第５表に示す通りいずれのキヤ
リア輸送物質との組み合わせにおいても良好であ
つた。[Table] Example 7 A carrier generation layer was formed in the same manner as in Example 5 except that Exemplified Compound B-(32) was replaced with Exemplified Compound B-(36). On top of this, 6 g of 1-(1-ethyl-4-carbazolyl)methylideneamino-indoline (compound K-(7)) and 10 g of polycarbonate "Panlite L-1250" (manufactured by Teijin Kasei) were added to 1,2-dichloroethane. Apply the solution dissolved in 70ml so that the film thickness after drying is 10μm and carry out carrier transfer. A feeding layer was formed to produce a photoreceptor of the present invention. Measurements were performed on this photoreceptor in the same manner as in Example 1, and E1/2 = 1.3 lux·sec and V R =
It was 0V. Example 8 An intermediate layer with a thickness of 0.05 μm made of vinyl chloride-vinyl acetate-maleic anhydride copolymer “Eslec MP-10” (manufactured by Sekisui Chemical Co., Ltd.) was provided on the surface of an aluminum drum with a diameter of 100 mm, and then Add 4 g of Exemplified Compound B-(26) to 400 ml of 1,2-dichloroethane.
The dispersion liquid was mixed with the following and dispersed for 24 hours using a ball mill dispersion machine, and the dispersion liquid was applied so that the film thickness after drying was 0.6 μm to form a carrier generation layer. Furthermore, on top of this, 4,4′-dimethyl-4″-(4
-methoxy)styryl-triphenylamine (compound K-(8) below) 30g and polycarbonate resin "Corpilon S-1000" (manufactured by Mitsubishi Gas Chemical Co., Ltd.) 50g
and 1,2-dichloroethane A carrier transport layer was formed by dissolving the solution in 400 ml and applying it to a film thickness of 13 μm after drying, thereby producing a drum-shaped photoreceptor. The photoreceptor created in this way was attached to a modified electrophotographic copying machine "U-Bix1600MR" (manufactured by Konishiroku Photo Industry Co., Ltd.), and the image was copied with high contrast, faithful to the original image, and clear copy. Got the image. Moreover, this did not change even after repeating it 10,000 times. Comparative Example 3 A drum-shaped comparative sample was prepared in the same manner as in Example 8, except that the exemplified compound B-(26) in Example 8 was replaced with a bisazo compound (G-(3)) represented by the following structural formula. When a photoreceptor was prepared and the copied images were evaluated in the same manner as in Example 8, only images with a lot of fog were obtained. Furthermore, as copying was repeated, the contrast of the copied image decreased, and after 2000 repetitions, almost no copied image could be obtained. Example 9 A layer of vinyl chloride-vinyl acetate-maleic anhydride copolymer "Eslec MF-10" (manufactured by Sekisui Chemical Co., Ltd.) was placed on a conductive support made of aluminum foil laminated on a polyester film.
A 0.05 μm intermediate layer is provided, and exemplified compound B is placed on top of the intermediate layer.
- Add 5 g of (74) and 3.3 g of polycarbonate resin "Panlite L-1250" (manufactured by Teijin Chemicals) to 100 ml of dichloromethane, and disperse in a ball mill for 24 hours. The dispersion was dried to a film thickness of 10 μm. A photoreceptor was prepared. The photoconductor obtained in the above manner is charged with a +
E1/2 and E1/2 in the same manner as in Example 1 except that 6KV was used.
VR was measured. The first result is E1/2=2.0lux・
sec and V R =0V. Example 10 1-Phenyl-3- as a carrier transport layer on a polyester film deposited with aluminum
(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline) Compound K below
-(9)6g and polyester resin "Byron 200" (manufactured by Toyobo Co., Ltd.) in 70 ml of 1,2-dichloroethane, and the film thickness after drying this solution.
It was applied to a thickness of 10 μm. Next, on top of this, 1 g of exemplified compound B-(9) and B-(10)
1g and 110ml of 1,2-dichloroethane,
A dispersion liquid dispersed for 24 hours using a ball mill was coated to a dry film thickness of 0.5 μm to form a carrier generation layer, thereby forming a photoreceptor of the present invention. The thus obtained photoreceptor was evaluated in the same manner as in Example 9, and found that E1/2 = 1.7 lux·sec and V R = +5V. Example 11 A layer of vinyl chloride-vinyl acetate-maleic anhydride copolymer "Eslec MF-10" (manufactured by Sekisui Chemical Co., Ltd.) was placed on a conductive support consisting of a polyester film laminated with aluminum foil.
A 0.05 μm intermediate layer is provided, and exemplified compound B is placed on top of the intermediate layer.
-(54) 4g and 4-methoxy-4'-methyl-4''-
(4-Methyl)styryl-triphenylamine (8 g of the following compound K-(10) and polycarbonate resin Add 3g of "Panlite L-1250" (manufactured by Teijin Chemicals) to 100ml of dichloroethane and disperse the dispersion with a sand grinder for 24 hours until the film thickness when dried.
A photoreceptor was prepared by coating the film to a thickness of 10 μm. The photoreceptor obtained in the above manner is charged with a +
E1/2 and E1/2 in the same manner as in Example 1 except that 6KV was used.
VR was measured. The first result is E1/2=1.0lux・
sec and V R =0V. Example 12 A 2% ethylenediamine solution of Exemplified Compound B-(66) was applied onto a polyester film laminated with aluminum to a dry film thickness of 0.5 μm to form a carrier generation layer. Furthermore, 4-methoxy-
4'-(4-chloro)-styryl-triphenylamine (compound K-(11) below), 4,4'-dimethyl-
4″-(4-bromo)-styryl-triphenylamine (compound K-(12) below) or 4-(4-octyl)-styryl-triphenylamine (compound K-(13) below) about 10g each and polycarbonate Resin (manufactured by Teijin Chemicals, Panlite L-1250) 14g
A solution prepared by dissolving the above in 140 ml of 1,2-dichloroethane was coated so as to have a dry film thickness of 12 μm, and dried to obtain photoreceptors containing three different carrier transport substances. These three types of photoreceptors are manufactured by Kawaguchi Electric Manufacturing Co., Ltd.
The following characteristics were evaluated using an electrostatic paper tester model SP-428 manufactured by Co., Ltd. Charge the material with a charging voltage of -6KV for 5 seconds, leave it in the dark for 5 seconds, and then irradiate it with halogen light so that the material surface illuminance is 35 lux. amount, E1/2) was measured. In addition, the surface potential (residual potential) V R after exposure with an exposure amount of 30 lux·sec was measured. As shown in Table 5, the results were good in combination with any carrier transport substance.
【表】
比較例 ４
例示化合物Ｂ−（66）を下記のビスアゾ化合物
（Ｇ−(4)）に代えた他は実施例12と同様にして比
較用感光体を作成し、特性評価を行なつた結果、
第６表に示す通り、キヤリア輸送物質によつて結
果にばらつきが出た。[Table] Comparative Example 4 A comparative photoreceptor was prepared in the same manner as in Example 12, except that the exemplified compound B-(66) was replaced with the following bisazo compound (G-(4)), and the characteristics were evaluated. As a result, As shown in Table 6, the results varied depending on the carrier transport substance.
【表】
実施例 13
実施例５で用いた中間層を設けた導電性支持体
上に、例示化合物Ｂ−（59）２ｇと１，２−ジク
ロロエタン100mlとをよく分散混合し、乾燥後の
膜厚が0.3μmになるように塗布しキヤリア発生層
を作成した。
次いでその上にキヤリア輸送物質として、４−
メトキシ−トリフエニルアミン（下記化合物Ｋ−
（14）６ｇとポリカーボネート「パンライトＬ−
1250」（帝人化成社製）
10ｇとを、１，２−ジクロロエタン90ｇに溶解し
た液を乾燥後の膜厚が10μmになるように塗布し
てキヤリア輸送層を形成し、本発明の感光体を作
成した。
この感光体について、25℃及び60℃の室内温度
における電子写真特性を、実施例７と同様にして
測定した。
結果を第７表に示す。[Table] Example 13 On the conductive support provided with the intermediate layer used in Example 5, 2 g of Exemplified Compound B-(59) and 100 ml of 1,2-dichloroethane were well dispersed and mixed, and the membrane after drying was prepared. A carrier generation layer was created by coating to a thickness of 0.3 μm. 4- is then added thereon as a carrier transport material.
Methoxy-triphenylamine (compound K- below)
(14) 6g and polycarbonate “Panlite L-
1250” (manufactured by Teijin Chemicals) A carrier transport layer was formed by dissolving 10 g of 1,2-dichloroethane in 90 g of 1,2-dichloroethane and applying the solution to a dry film thickness of 10 μm, thereby producing a photoreceptor of the present invention. The electrophotographic properties of this photoreceptor at room temperatures of 25° C. and 60° C. were measured in the same manner as in Example 7. The results are shown in Table 7.
【表】
以上の結果から明らかなように、本発明の電子
写真感光体は高温においても感度、残留電位特性
が良好であり、熱に対して安定であることがわか
る。
実施例 14
実施例５で用いた中間層を設けた導電性支持体
上に例示化合物Ｂ−(3)２ｇと１，２−ジクロロエ
タン110mlとをよく分散混合し乾燥後の膜厚が
0.3μmになるように塗布してキヤリア発生層を作
成した。
このキヤリア発生層のUV光に対する耐久性を
試験するため、30cm離れた位置に超高圧水銀ラン
プ（東京芝浦電機社製）を置き、10分間
1500cd／cm2のUV光を照射した。
次に、このUV光照射済みのキヤリア発生層の
上にキヤリア輸送物質として、３−（ｐメトキシ
スチリル）−９−（ｐ−メトキシフエニル）カルバ
ゾール（下記化合物Ｋ−（15））７ｇとポリカーボ
ネート〔パンライトＬ−1250〕（帝人化成社製）
10ｇとを、１，２−ジクロロエタン
90ｇに溶解した液を乾燥後の膜厚が12μmになる
ように塗布してキヤリア輸送層を形成し、本発明
の感光体を作成した。
この感光体について、実施例５と同様の測定を
行なつた。結果を第８表に示す。
実施例 15
キヤリア発生層形成後にUV光を照射しないほ
かは、実施例14と同様にして本発明の感光体を作
成し、実施例５と同様の測定を行なつた。
結果を第８表に示す。[Table] As is clear from the above results, the electrophotographic photoreceptor of the present invention has good sensitivity and residual potential characteristics even at high temperatures, and is stable against heat. Example 14 2 g of Exemplified Compound B-(3) and 110 ml of 1,2-dichloroethane were well dispersed and mixed on the conductive support provided with the intermediate layer used in Example 5, and the film thickness after drying was
A carrier generation layer was created by coating to a thickness of 0.3 μm. In order to test the durability of this carrier generation layer against UV light, an ultra-high pressure mercury lamp (manufactured by Tokyo Shibaura Electric Co., Ltd.) was placed 30 cm away from the carrier for 10 minutes.
UV light of 1500 cd/cm 2 was irradiated. Next, 7 g of 3-(p-methoxystyryl)-9-(p-methoxyphenyl)carbazole (compound K-(15) below) and polycarbonate were added as a carrier transport material onto this carrier generation layer that had been irradiated with UV light. [Panlite L-1250] (manufactured by Teijin Chemicals)
10g and 1,2-dichloroethane A carrier transport layer was formed by applying a solution dissolved in 90 g of the solution to a dry film thickness of 12 μm, thereby producing a photoreceptor of the present invention. The same measurements as in Example 5 were performed on this photoreceptor. The results are shown in Table 8. Example 15 A photoreceptor of the present invention was prepared in the same manner as in Example 14, except that UV light was not irradiated after the carrier generation layer was formed, and the same measurements as in Example 5 were carried out. The results are shown in Table 8.
【表】
以上の結果から明らかなように、本発明の電子
写真感光体はUV光照射に対して感度・残留電位
特性に優れ、受容電位の変動量も小さく、光に対
して安定であることが理解できる。
比較例 ５
化合物Ｂ−(3)を下記のビスアゾ化合物（Ｇ−
(5)）に変えた他は実施例14及び実施例15と
同様にして感光体を作成し実施例５と同様の測定
を行なつた。結果を第９表に示す。[Table] As is clear from the above results, the electrophotographic photoreceptor of the present invention has excellent sensitivity and residual potential characteristics against UV light irradiation, has small fluctuations in acceptance potential, and is stable against light. I can understand. Comparative Example 5 Compound B-(3) was converted into the following bisazo compound (G-
Same as Example 14 and Example 15 except that (5)) was changed. A photoreceptor was prepared in the same manner and the same measurements as in Example 5 were performed. The results are shown in Table 9.
【表】
以上の結果から明らかなように、上記化合物を
用いて作成した感光体は、UV光照射によつて感
度・残留電位特性は劣化し、受容電位の変動量も
大きい。
実施例 16
実施例５において例示化合物Ｂ−（32）をＢ−
(1)に代えた他は同様にしてドラム状の感光体を作
成した。この感光体の9nmにおいける分光感度は
950voH・cm2μW-1・sec-1（半減衰速度）であつ
た。この本発明の感光体を感光体表面でのレーザ
ー光強度が、0.85mWとなる半導体レーザー
（9nm）を装着した実験機により実写テストを行
なつた。
感光体の表面を−6KVに帯電した後、レーザ
ー露光し−250Vのバイアス電圧で反転現像した
ところ、カブリのない良好な画像が得られた。
比較例 ６
実施例16において例示化合物Ｂ−(1)に代えて下
記の比較用ビスアゾ化合物Ｇ−(6)を用いた他は同
様にして比較用感光体を得た。
この感光体の9μmにおける分光感度は50voH・
cm2・μmW-1・sec-1（半減衰速度）であつた。こ
の比較用感光体を用いて実施例14と同様に半導体
レーザーによる実写テストを行なつたがカブリが
多く良好な画像は得られなかつた。
実施例 17−30
実施例５において、例示化合物Ｂ−（32）（電荷
発生物質）及び化合物Ｋ−(5)（電荷輸送物質）を
表10のように代えた他は同様にしてトラム状の感
光体を作成した。この感光体の790nmにおける分
光感度は表10のようであり、本感光体（実施例17
−30）を用いた、実施例16と同様の写実テストで
は、いずれもカブリのない良好な画像が得られ
た。[Table] As is clear from the above results, the sensitivity and residual potential characteristics of the photoreceptor prepared using the above compound deteriorate due to UV light irradiation, and the amount of variation in acceptance potential is large. Example 16 In Example 5, Exemplified Compound B-(32) was replaced with B-
A drum-shaped photoreceptor was produced in the same manner except that (1) was replaced. The spectral sensitivity of this photoreceptor at 9 nm is
It was 950voH・cm 2 μW -1・sec -1 (half decay rate). The photoreceptor of the present invention was subjected to an actual photographic test using an experimental machine equipped with a semiconductor laser (9 nm) that produced a laser light intensity of 0.85 mW on the surface of the photoreceptor. After the surface of the photoreceptor was charged to -6 KV, it was exposed to laser light and reverse development was performed at a bias voltage of -250 V. A good image without fogging was obtained. Comparative Example 6 A comparative photoreceptor was obtained in the same manner as in Example 16, except that the following comparative bisazo compound G-(6) was used in place of Exemplified Compound B-(1). The spectral sensitivity of this photoreceptor at 9μm is 50voH・
cm 2・μmW -1・sec -1 (half decay rate). Using this comparative photoreceptor, an actual photographic test using a semiconductor laser was conducted in the same manner as in Example 14, but there was a lot of fog and no good images could be obtained. Example 17-30 A tram-shaped sample was prepared in the same manner as in Example 5, except that the exemplary compound B-(32) (charge-generating substance) and compound K-(5) (charge-transporting substance) were changed as shown in Table 10. A photoreceptor was created. The spectral sensitivity of this photoconductor at 790 nm is as shown in Table 10, and the spectral sensitivity of this photoconductor (Example 17) is as shown in Table 10.
-30) in the same manner as in Example 16, good images with no fog were obtained in all cases.
【表】【table】
【表】
以上の実施例、比較例の結果から明らかなよう
に本発明の感光体は比較用電子写真感光体に比
べ、安定性、感度、耐久性広範なキヤリア輸送物
質との組み合わせ等の特性において著しく優れた
ものである。
（発明の効果）
本発明によつて、感光体の感光層を構成する光
導電性物質として前記一般式〔〕で表されるア
ゾ化合物を使用することにより、本発明の目的で
ある熱および光に対して安定であり、また電荷保
持力、感度、残留電位等の電子写真特性において
優れており、かつ繰り返し使用した時にも疲労変
化が少なく、さらに780nm以上の長波長領域にお
いても十分な感度を有する優れた感光体を作成す
ることができる。【table】 As is clear from the results of the above Examples and Comparative Examples, the photoreceptor of the present invention is significantly superior to comparative electrophotographic photoreceptors in properties such as stability, sensitivity, durability, and combination with a wide range of carrier transport materials. It is something that (Effects of the Invention) According to the present invention, by using an azo compound represented by the general formula [] as a photoconductive substance constituting the photosensitive layer of a photoreceptor, heat and light, which is the object of the present invention, can be It also has excellent electrophotographic properties such as charge retention, sensitivity, and residual potential, and shows little fatigue change even after repeated use, and has sufficient sensitivity even in the long wavelength region of 780 nm or more. It is possible to create an excellent photoreceptor with
第１図〜第６図はそれぞれ本発明の感光体の機
械的構成例について示す断面図であつて図中の１
〜７はそれぞれ以下の事を表わす。
１……導電性支持体、２……キヤリア発生層、
３……キヤリア輸送層、４……感光層、５……中
間層、６……キヤリア輸送物質を有する層、７…
…キヤリア発生物質。
FIGS. 1 to 6 are cross-sectional views showing examples of the mechanical structure of the photoreceptor of the present invention.
~7 represent the following, respectively. 1... Conductive support, 2... Carrier generation layer,
3... Carrier transport layer, 4... Photosensitive layer, 5... Intermediate layer, 6... Layer having a carrier transport substance, 7...
...Carrier generating substance.
Claims (1)
るアゾ化合物を含有する感光層を有することを特
徴とする感光体。 一般式〔〕 〔式中、Y1及びY2は水素原子、ハロゲン原子、
シアノ基、ハイドロキシ基、アルキル基またはア
ルコキシ基、ｍ及びｎは０乃至２の整数をそれぞ
れ表わし、ｍとｎが共に０であることはない。 Ａは【式】 【式】【式】 または【式】であつて、ここに Ｚは置換若しくは未置換の芳香族炭素環、または
は置換若しくは未置換の芳香族複素環を構成する
に必要な原子群、Ｑは置換若しくは未置換のカル
バモイル基、または置換若しくは未置換のスルフ
アモイル基、R1は水素原子、置換若しくは未置
換のアルキル基、置換若しくは未置換のアミノ
基、置換若しくは未置換のカルバモイル基、カル
ボキシル基及びそのエステル基、またはシアノ
基、A′は置換若しくは未置換のアリール基、R2
及びR3は置換若しくは未置換のアルキル基、置
換若しくは未置換のアラルキル基、または置換若
しくは未置換のアリール基を表す。〕 ２ 前記感光層がキヤリア輸送物質とキヤリア発
生物質とを含有し、当該キヤリア発生物質が前記
一般式〔〕で表わされるアゾ化合物である特許
請求の範囲第１項記載の感光体。 ３ 前記感光層が、キヤリア発生物質を含有する
キヤリア発生層と、キヤリア輸送物質を含有する
キヤリア輸送層との積層体で構成されている特許
請求の範囲第１項または第２項記載の感光体。[Scope of Claims] 1. A photoreceptor comprising a photosensitive layer containing an azo compound represented by the following general formula [] on a conductive support. General formula [] [In the formula, Y 1 and Y 2 are hydrogen atoms, halogen atoms,
A cyano group, a hydroxy group, an alkyl group, or an alkoxy group, m and n each represent an integer of 0 to 2, and m and n cannot both be 0. A is [Formula] [Formula] [Formula] or [Formula], where Z is a substituted or unsubstituted aromatic carbocycle, or a substituted or unsubstituted aromatic heterocycle. Atom group, Q is a substituted or unsubstituted carbamoyl group, or a substituted or unsubstituted sulfamoyl group, R 1 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbamoyl group group, carboxyl group and its ester group, or cyano group, A′ is a substituted or unsubstituted aryl group, R 2
and R 3 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. 2. The photoreceptor according to claim 1, wherein the photosensitive layer contains a carrier transporting substance and a carrier generating substance, and the carrier generating substance is an azo compound represented by the general formula []. 3. The photoreceptor according to claim 1 or 2, wherein the photosensitive layer is constituted by a laminate of a carrier generation layer containing a carrier generation substance and a carrier transport layer containing a carrier transport substance. .
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7237584A JPS60214366A (en) | 1984-04-10 | 1984-04-10 | Photosensitive body |
| US06/700,534 US4579800A (en) | 1984-03-27 | 1985-02-11 | Azo photoreceptor |
| DE8585300955T DE3563276D1 (en) | 1984-03-27 | 1985-02-13 | Photoreceptor |
| EP85300955A EP0156481B1 (en) | 1984-03-27 | 1985-02-13 | Photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7237584A JPS60214366A (en) | 1984-04-10 | 1984-04-10 | Photosensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60214366A JPS60214366A (en) | 1985-10-26 |
| JPH0220976B2 true JPH0220976B2 (en) | 1990-05-11 |
Family
ID=13487486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7237584A Granted JPS60214366A (en) | 1984-03-27 | 1984-04-10 | Photosensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60214366A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62227156A (en) * | 1986-03-28 | 1987-10-06 | Konika Corp | Electrophotographic sensitive body having specified undercoat layer |
-
1984
- 1984-04-10 JP JP7237584A patent/JPS60214366A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60214366A (en) | 1985-10-26 |
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