JPH0342669A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0342669A JPH0342669A JP17744589A JP17744589A JPH0342669A JP H0342669 A JPH0342669 A JP H0342669A JP 17744589 A JP17744589 A JP 17744589A JP 17744589 A JP17744589 A JP 17744589A JP H0342669 A JPH0342669 A JP H0342669A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- carbon atoms
- groups
- electrophotographic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000000732 arylene group Chemical group 0.000 claims abstract description 4
- -1 disazo compound Chemical class 0.000 claims description 79
- 108091008695 photoreceptors Proteins 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 230000035945 sensitivity Effects 0.000 abstract description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 5
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 3
- 230000006866 deterioration Effects 0.000 abstract description 3
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- 230000036211 photosensitivity Effects 0.000 abstract description 3
- 125000003367 polycyclic group Chemical group 0.000 abstract description 3
- 230000003252 repetitive effect Effects 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 49
- 125000004432 carbon atom Chemical group C* 0.000 description 38
- 239000002800 charge carrier Substances 0.000 description 33
- 125000001424 substituent group Chemical group 0.000 description 21
- 230000032258 transport Effects 0.000 description 21
- 239000011230 binding agent Substances 0.000 description 18
- 239000000975 dye Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000049 pigment Substances 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000004663 dialkyl amino group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000001427 coherent effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- IQZZFVDIZRWADY-UHFFFAOYSA-N isocoumarin Chemical compound C1=CC=C2C(=O)OC=CC2=C1 IQZZFVDIZRWADY-UHFFFAOYSA-N 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- PXGXZGVGEDLSMW-UHFFFAOYSA-M (2e)-3-methyl-2-[(e)-3-(3-methyl-1,3-benzoxazol-3-ium-2-yl)prop-2-enylidene]-1,3-benzoxazole;iodide Chemical compound [I-].O1C2=CC=CC=C2[N+](C)=C1/C=C/C=C1/N(C)C2=CC=CC=C2O1 PXGXZGVGEDLSMW-UHFFFAOYSA-M 0.000 description 1
- DGVZQSMXUHGJHU-UHFFFAOYSA-N 1,2-dinitrofluoren-9-one Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C2=C1 DGVZQSMXUHGJHU-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- FQGZKQSSKVAZPH-UHFFFAOYSA-N 1-[2-[ethyl-(2-hydroxy-2-methylpropyl)amino]ethylamino]-4-methylthioxanthen-9-one;hydrochloride Chemical compound Cl.S1C2=CC=CC=C2C(=O)C2=C1C(C)=CC=C2NCCN(CC)CC(C)(C)O FQGZKQSSKVAZPH-UHFFFAOYSA-N 0.000 description 1
- LFKNYYQRWMMFSM-UHFFFAOYSA-N 1-ethyl-9h-carbazole;formaldehyde Chemical compound O=C.N1C2=CC=CC=C2C2=C1C(CC)=CC=C2 LFKNYYQRWMMFSM-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
- WCQLACGUXBFKGM-UHFFFAOYSA-N 2-(2,4,7-trinitro-1-oxo-2h-fluoren-9-ylidene)propanedinitrile Chemical compound [O-][N+](=O)C1=CC=C2C(C(=CC(C3=O)[N+](=O)[O-])[N+]([O-])=O)=C3C(=C(C#N)C#N)C2=C1 WCQLACGUXBFKGM-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 240000002834 Paulownia tomentosa Species 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
- 241000220317 Rosa Species 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- KCOHNVZBEQFNJX-UHFFFAOYSA-M [6-(2,6-diphenylthiopyran-4-ylidene)cyclohexa-2,4-dien-1-ylidene]-dimethylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CN(C)C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=[S+]C(C=2C=CC=CC=2)=C1 KCOHNVZBEQFNJX-UHFFFAOYSA-M 0.000 description 1
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- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
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Landscapes
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規なヒ矛宜アゾ化合物を含有する電子写真
感光層を有することを特(マとした電子写真感光体に関
するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor having an electrophotographic photosensitive layer containing a novel azo compound.
従来、電子写真感光体に用いられる光KN組成物として
は、セレン、硫化カドミウム、酸化亜鉛、アモルファス
シリコンなどの無機物質がよく知られている。これらの
無機物質は、良好なる電子写真特性即ち、極めて良好な
光導電性と暗所での電荷受容性及び絶縁性を備えている
という長所を持つ。しかしその反面、様々な欠点がある
。例えば、セレン感光体は製造コストが高く、可撓性が
なく、熱や機械的衝撃に弱いなどの欠点を持つ。硫化カ
ドミウム感光体は、材料にカド完つムという有毒物質を
用いているため公害性に問題がある。酸化亜鉛は、長期
間繰り返し使用した場合、画像の安定性に難点がある。Conventionally, inorganic substances such as selenium, cadmium sulfide, zinc oxide, and amorphous silicon are well known as photo-KN compositions used in electrophotographic photoreceptors. These inorganic materials have the advantage of having good electrophotographic properties, ie very good photoconductivity, charge acceptance in the dark, and insulation properties. However, on the other hand, there are various drawbacks. For example, selenium photoreceptors have drawbacks such as high production cost, lack of flexibility, and weakness against heat and mechanical shock. Cadmium sulfide photoreceptors have pollution problems because they use a toxic substance called cadmium as a material. Zinc oxide has a drawback in image stability when used repeatedly over a long period of time.
さらにアモルファスシリコン感光体は、製造コストが極
めて高く、感光体表面の劣化を防止するために特殊な表
面処理を要する等の欠点を持つ。Furthermore, amorphous silicon photoreceptors have drawbacks such as extremely high manufacturing costs and the need for special surface treatment to prevent deterioration of the photoreceptor surface.
近年、これら無機物質の欠点を排除するためにいろいろ
の有機物質を用いた電子写真感光体が提案され、実用に
供されているものもある。たとえば、ポリ−N−ビニル
カルバシールド2. 4. 7トリニトロフルオレノン
ー9−オンとからなる電子写真感光体(米国特許3,4
84,237)、ポリ−N−ビニルカルバゾールをビリ
リウム塩系色素で増感したもの(特公昭48−2565
8)、染料と樹脂とからなる共晶錯体を主成分とする電
子写真感光体(特開昭47−10,735)などである
。In recent years, electrophotographic photoreceptors using various organic materials have been proposed in order to eliminate the drawbacks of these inorganic materials, and some of them have been put into practical use. For example, poly-N-vinylcarbashield 2. 4. 7 trinitrofluorenone-9-one (U.S. Pat. No. 3,4
84,237), poly-N-vinylcarbazole sensitized with biryllium salt dye (Japanese Patent Publication No. 48-2565
8), an electrophotographic photoreceptor whose main component is a eutectic complex consisting of a dye and a resin (Japanese Unexamined Patent Publication No. 1983-10735).
また、ペリレン顔料(米国特許第3,371゜884号
等)、フタロシアニン顔料(米国特許第3、−397.
086号、第4,666.802号等)、アズレニウム
塩系顔料(特開昭59−53850.6m−212,5
42等)スクアリウム塩系顔料(米国特許第4.396
,610号、第4 644 082号等)、多環率ノン
系顔料(特開昭51−184.348.62−28.7
38等)等の有機顔料や、次↓こ示ずようなアゾ顔料を
主成分とする電子写真感光体も景近活発に研究が行われ
、数多くの提案がなされている。Also, perylene pigments (U.S. Pat. No. 3,371.884, etc.), phthalocyanine pigments (U.S. Pat. No. 3,-397.
086, No. 4,666.802, etc.), azulenium salt pigments (JP-A-59-53850.6m-212,5)
42 etc.) Squarium salt pigments (U.S. Patent No. 4.396)
, No. 610, No. 4 644 082, etc.), non-polycyclic pigments (JP-A-51-184.348.62-28.7)
Electrophotographic photoreceptors based on organic pigments such as 38) and azo pigments such as those shown below have been actively researched by Kageuchika, and numerous proposals have been made.
(ビスアゾ系顔料)
特開昭47−37,543、特公昭60−594]、特
公昭60−45.664、特開昭56116.039、
特開昭58 123.541、特開昭61−260,2
50、特開昭61228.453、特開昭61−275
.849、特開昭61275.850
(トリスアゾ系顔料)
米国特許第4,436.800号、同第4.439 5
06号、特開昭51−132,347、特開昭55−6
9,148、特開昭57−195767、特開昭57−
200.045、特開昭57−204,556、特開昭
58−31,340、特開昭5.8−31. 34 l
、特開昭58−154560、特開昭58−160,3
58、特開昭511160.359、特開昭59−12
7.044、特開昭59−196,366、特開昭59
204.046、特開昭59−204,841特開昭5
!ll−218,454、特開昭60−111.249
、特開昭60−111.250、特開昭61−11.7
54、特開昭6に22,346、特開昭61−35,4
51、特開昭61−67.865、特開昭61−121
.−059、特開昭61−163,969、特開昭61
−179746、特開昭61−230,157、特開昭
61−251,862、特開昭61−251,865、
特開昭61−269,164、特開昭6221.157
、特開昭62−78,563、特開昭62−115,4
52
(テトラキスアゾ系顔料)
米国特許第4,447,513号、特開昭60108.
857、特開昭60−108,858、特開昭60−1
11.247、特開昭60−111’、24B、特開昭
60−118,843、特開昭60−176.046、
特開昭61−103157、特開昭61−117.55
9、特開昭61−182.051、特開昭61−194
.447、特開昭61−196,253、特開昭612
12.848、特開昭61−240,246、特開昭6
1−273,548、特開昭61−284.769、特
開昭62.18,56.5、特開昭62−18,566
、特開昭62−19,875/
〔発明が解決しようとする課題〕
これらの電子写真感光体は、前記無機電子写真感光体の
機械的特性及び可撓性もある程度まで改善したものの、
感度がまた不十分であり、また多数回の繰り返し使用時
に電気的特性が変化する場合があり、電子写真感光体と
して要求を必ずしも十分満足するものではなかった。(Bisazo pigment) JP 47-37543, JP 60-594], JP 60-45.664, JP 56116.039,
Unexamined Japanese Patent Publication No. 58 123.541, Unexamined Japanese Patent Publication No. 61-260.2
50, JP 61228.453, JP 61-275
.. 849, JP 61275.850 (Trisazo pigment) U.S. Patent No. 4,436.800, U.S. Patent No. 4.439 5
No. 06, JP-A-51-132,347, JP-A-55-6
9,148, JP-A-57-195767, JP-A-57-
200.045, JP-A-57-204,556, JP-A-58-31,340, JP-A-5.8-31. 34 l
, JP-A-58-154560, JP-A-58-160,3
58, JP 511160.359, JP 59-12
7.044, JP-A-59-196,366, JP-A-59-1966
204.046, JP-A-59-204,841 JP-A-5
! ll-218,454, JP-A-60-111.249
, JP-A-60-111.250, JP-A-61-11.7
54, 22,346 in Unexamined Japanese Patent Publication No. 1983, No. 61-35, 4
51, JP-A-61-67.865, JP-A-61-121
.. -059, JP-A-61-163,969, JP-A-61-163,969
-179746, JP 61-230,157, JP 61-251,862, JP 61-251,865,
JP-A No. 61-269,164, JP-A No. 6221.157
, JP-A-62-78,563, JP-A-62-115,4
52 (Tetrakisazo pigment) U.S. Patent No. 4,447,513, JP-A-60108.
857, JP-A-60-108, 858, JP-A-60-1
11.247, JP-A-60-111', 24B, JP-A-60-118,843, JP-A-60-176.046,
JP-A-61-103157, JP-A-61-117.55
9, JP-A-61-182.051, JP-A-61-194
.. 447, JP 61-196, 253, JP 612
12.848, JP-A-61-240,246, JP-A-6
1-273,548, JP-A No. 61-284.769, JP-A No. 62-18, 56.5, JP-A No. 62-18,566
, JP-A-62-19,875/ [Problems to be Solved by the Invention] Although these electrophotographic photoreceptors have improved the mechanical properties and flexibility of the inorganic electrophotographic photoreceptors to a certain extent,
The sensitivity was also insufficient, and the electrical characteristics sometimes changed after repeated use many times, so they did not necessarily fully satisfy the requirements for electrophotographic photoreceptors.
本発明の目的は、高感度で高耐久性を有する新規な電子
写真感光体を提供することである。また、発明の他の目
的は、繰り返し使用しても光感度の低下の少ない新規な
電子写真感光体を提供することである。An object of the present invention is to provide a novel electrophotographic photoreceptor having high sensitivity and high durability. Another object of the invention is to provide a new electrophotographic photoreceptor that exhibits little reduction in photosensitivity even after repeated use.
本発明は、導電性支持体上に、電荷担体輸送化合物及び
電荷担体発生化合物を含有した層より成るか、または電
荷担体輸送化合物含有層及び、電荷発生化合物含有層よ
り成る電子写真感光体において、電荷担体発生化合物と
して下記の一般式〔1〕で表される新規なジスアゾ化合
物を含有することを特徴とする電子写真感光体に関する
ものである。The present invention provides an electrophotographic photoreceptor comprising a layer containing a charge carrier transporting compound and a charge carrier generating compound, or a layer containing a charge carrier transporting compound and a layer containing a charge carrier generating compound, on a conductive support. The present invention relates to an electrophotographic photoreceptor characterized by containing a novel disazo compound represented by the following general formula [1] as a charge carrier generating compound.
Cp−N=N−Ar”−C=C−Ar’−C= C−A
r5=N=N−Cp (1:]5 R6
一般式〔1〕において、Ar’ 、Ar2及びAr3は
アリーレン基、2価の縮合多環式芳香族基または2価の
複素芳香環基を表す。Cpはカプラー残基を表す。Cp-N=N-Ar''-C=C-Ar'-C= C-A
r5=N=N-Cp (1:]5 R6 In the general formula [1], Ar', Ar2 and Ar3 represent an arylene group, a divalent fused polycyclic aromatic group or a divalent heteroaromatic group .Cp represents a coupler residue.
R5及びR6は水素原子、アルキル基、アルコキシ基、
シアノ基、ニトロ基またはハロゲン原子を表す。R5 and R6 are hydrogen atoms, alkyl groups, alkoxy groups,
Represents a cyano group, nitro group or halogen atom.
一般式〔1〕で表されるジスアゾ化合物についてさらに
詳しく説明する。The disazo compound represented by the general formula [1] will be explained in more detail.
Ar’ 、Ar’及びAr”としては、例えばフェニレ
ン、ナフタレン、アントリレン、ビフェニレン、ターフ
ェニレン等のようなアリーレン基、インデン、フルオレ
ン、アセナフテン、ペリレン、フルオレノン、アントロ
ン、アントラキノン、ベンゾアントロン、イソクマリン
等の縮合多環式芳香環より導いた2価の基、ピリジン、
キノリン、オキサゾール、チアゾール、オキサジアゾー
ル、ベンゾオキサゾール、ベンゾイミダゾール、ベンゾ
チアゾール、ベンゾドアリシール、ジベンゾフラン、カ
ルバゾール、キサンチン等の複素芳香環より導いた2価
の基が挙げられる。Examples of Ar', Ar' and Ar'' include arylene groups such as phenylene, naphthalene, anthrylene, biphenylene, and terphenylene; condensation groups such as indene, fluorene, acenaphthene, perylene, fluorenone, anthrone, anthraquinone, benzanthrone, and isocoumarin; Divalent group derived from polycyclic aromatic ring, pyridine,
Examples include divalent groups derived from heteroaromatic rings such as quinoline, oxazole, thiazole, oxadiazole, benzoxazole, benzimidazole, benzothiazole, benzodoarysyl, dibenzofuran, carbazole, and xanthine.
Ar1、Ar2及びAr3が置換基を有する場合、その
置換基としては、炭素数1〜18のアルキル基、炭素数
1〜18のアルコキシ基、炭素数1〜18のアルキル基
を2個有するジアルキルアミノ基、炭素数1〜18のア
シル基、炭素数1〜18のアシルオキシ基、炭素数1〜
18のアミド基、炭素数6〜15のアリール基、炭素数
6〜15のアリールオキシ基、ハロゲン原子、ヒドロキ
シ基、カルボキシル基、ニトロ基、シアノ基、トリフル
オロメチル基等を挙げることができる。When Ar1, Ar2 and Ar3 have a substituent, the substituent is an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, or a dialkylamino having two alkyl groups having 1 to 18 carbon atoms. group, acyl group having 1 to 18 carbon atoms, acyloxy group having 1 to 18 carbon atoms, 1 to 18 carbon atoms
Examples include an amide group having 18 carbon atoms, an aryl group having 6 to 15 carbon atoms, an aryloxy group having 6 to 15 carbon atoms, a halogen atom, a hydroxy group, a carboxyl group, a nitro group, a cyano group, and a trifluoromethyl group.
R5またはR6がアルキル基の場合、具体例としては炭
素数1〜6のアルキル基(例えばメチル基、エチル基、
n−プロピル基、n−ブチル基等)をあげることができ
る。When R5 or R6 is an alkyl group, specific examples include alkyl groups having 1 to 6 carbon atoms (e.g. methyl group, ethyl group,
n-propyl group, n-butyl group, etc.).
R5またはR6がアルコキシ基の場合、具体例としては
炭素数1〜6のアルコキシ基(例えばメトキシ基、エト
キシ基、n−プロポキシ基、nブトロキシ基等)を挙げ
ることができる。When R5 or R6 is an alkoxy group, specific examples include alkoxy groups having 1 to 6 carbon atoms (eg, methoxy group, ethoxy group, n-propoxy group, n-butroxy group, etc.).
R5またはR6がハロゲン基の場合、具体例としてフッ
素原子、塩素原子、臭素原子及びヨウ素原子を挙げるこ
とができる。When R5 or R6 is a halogen group, specific examples include fluorine atom, chlorine atom, bromine atom and iodine atom.
cpは、ジアゾニウム塩と反対する公知のカプラーの残
基を表し、電子写真感光体の電荷発生化合物として用い
られるアゾ化合物の公知のカプラー残基が好ましい。こ
のうち特に、Cpとしては、以下の構造に示されるカプ
ラー残基が好ましい。cp represents a known coupler residue opposite to a diazonium salt, and is preferably a known coupler residue of an azo compound used as a charge generating compound in an electrophotographic photoreceptor. Among these, particularly preferred as Cp are coupler residues shown in the structure below.
0
3
11
40
COCH3
上記Cpの一般式中のXは、ヒドロキシ基とYとが結合
しているヘンゼン環と縮合して、ナフクレン環、アント
ラセン環などの芳香族環よたは、1′ントール環、カル
バゾール環、ヘンヅカルハゾル環、ジヘンゾフラン環、
などの複素環を形成するのに必要な原子団を衷ず。0 3 11 40 COCH3 In the above general formula of Cp, X is condensed with the Hensen ring to which the hydroxy group and Y are bonded to form an aromatic ring such as a naphculene ring or anthracene ring, or a 1'enthol ring. , carbazole ring, henzukalhazol ring, dihenzofuran ring,
The atomic groups necessary to form a heterocycle such as are not included.
Xが置換基を有する芳香族環または複素環系の場合、置
換基としてはハロゲン原子(例えば、フッ素原子、塩素
原子、臭素原子′4)、炭素数l〜18のアルキル基(
例えば、メチル基、エチル基、プロピル基、ブチル基、
ドデシル基、オクタデシル基、イソプロピル基、イソブ
チル基等)、I・リフルオロメチル基、ニトロ基、アミ
ン基、シアノ基、炭素数1〜8のアルコキシ基(例えば
メトキシ基、エトキシ基、ブトキシ基等)等があげられ
、置換基の個数及び置換位置は任意である。When X is an aromatic ring or a heterocyclic ring having a substituent, examples of the substituent include a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom), an alkyl group having 1 to 18 carbon atoms (
For example, methyl group, ethyl group, propyl group, butyl group,
dodecyl group, octadecyl group, isopropyl group, isobutyl group, etc.), I-lifluoromethyl group, nitro group, amine group, cyano group, alkoxy group having 1 to 8 carbon atoms (e.g. methoxy group, ethoxy group, butoxy group, etc.) etc., and the number and substitution positions of substituents are arbitrary.
Yは−CONR3R’ −CONHN=CR11R’
C0OR”または置換基を有していてもよい複素5員環
または複素6員環を表す。Y is -CONR3R'-CONHN=CR11R'
C0OR'' or a 5-membered heterocyclic ring or a 6-membered heterocyclic ring which may have a substituent.
R1は炭素数1〜12のアルキル基またはアリル基を表
す。R1 represents an alkyl group or an allyl group having 1 to 12 carbon atoms.
R1が無置換のアルキル基の場合、その具体例としてメ
チル基、エチル基、プロピル基、ブチル基、ペンチル基
、ヘキシル基、イソプロピル基、イソブチル基、イソア
ミル基、イソヘキシル基、ネオペンチル基、ter t
−ブチル基等をあげることができる。When R1 is an unsubstituted alkyl group, specific examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group, isobutyl group, isoamyl group, isohexyl group, neopentyl group, tert
-Butyl group, etc. can be mentioned.
R1が置換アルキル基の場合、置換基としてはヒドロキ
シ基、炭素数1〜12のアルコキシ基、シアノ基、アミ
ノ基、炭素数1〜12のアルキルアミノ基、炭素数1〜
12のアルキル基を2個有するジアルキルアミノ基、ハ
ロゲン原子、炭素数6〜15の了り−ル基等がある。そ
の例として、ヒドロキシアルキル基(例えば、ヒドロキ
シメチル基、2−ヒドロキシエチル基、3−ヒドロキシ
プロピル基、2−ヒドロキシプロピル基等)、アルコキ
シアルキル基(例えぽ、メトキシメチル基、2−メトキ
シエチル基、3−メトキシプロピル基、エトキシメチル
基、2−エトキシエチル基等)、シアノアルキル基(例
えば、シアノメチル基、2シアノエチル基等)、アミノ
アルギル基(例えば、アミノメチル基、2−アミノエチ
ル基、3アミノプロピル基等)、(アルキルアミノ)ア
ルキル基(例えば、(メチルアミノ)メチル基、2(メ
チルアく))エチル基、(エチルアミノ)メチル基等)
、(ジアルキルアミノ)アルキル基(例えば、(ジメチ
ルアミノ)メチル基、2(ジメチルアミノ)エチル基笠
)、ハロゲノアルキル基(例えば、フルオロメチル基、
トリフルオロメチル基、クロロメチル基等)、アラルキ
ル基(例えば、ヘンシル基、フェネチル基等)をあげる
ことができる。When R1 is a substituted alkyl group, the substituent includes a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, a cyano group, an amino group, an alkylamino group having 1 to 12 carbon atoms, and an alkylamino group having 1 to 12 carbon atoms.
Examples thereof include a dialkylamino group having two alkyl groups of 12, a halogen atom, and an oryl group having 6 to 15 carbon atoms. Examples thereof include hydroxyalkyl groups (e.g., hydroxymethyl group, 2-hydroxyethyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, etc.), alkoxyalkyl groups (e.g., methoxymethyl group, 2-methoxyethyl group, etc.). , 3-methoxypropyl group, ethoxymethyl group, 2-ethoxyethyl group, etc.), cyanoalkyl group (e.g., cyanomethyl group, 2-cyanoethyl group, etc.), aminoargyl group (e.g., aminomethyl group, 2-aminoethyl group, 3-methoxypropyl group, 2-ethoxyethyl group, etc.), (aminopropyl group, etc.), (alkylamino)alkyl group (e.g., (methylamino)methyl group, 2(methylalk))ethyl group, (ethylamino)methyl group, etc.)
, (dialkylamino)alkyl group (e.g., (dimethylamino)methyl group, 2(dimethylamino)ethyl group), halogenoalkyl group (e.g., fluoromethyl group,
trifluoromethyl group, chloromethyl group, etc.), and aralkyl groups (eg, Hensyl group, phenethyl group, etc.).
R1が無置換アリール基の場合、その具体例としてツユ
ニル基、ナフチル基、アントリル基等をあげることがで
きる。When R1 is an unsubstituted aryl group, specific examples thereof include a thuunyl group, a naphthyl group, an anthryl group, and the like.
R1が置換了り−ル基の場合、置換基としてはヒドロキ
シ基、炭素数1〜12のアルコキン基、シアノ基、アミ
ノ基、炭素数1〜12のアルキルアミノ基、炭素数1〜
12のアルキル基を2個有するジアルキルアミノ基、炭
素数6〜12の了り−ルアゾ基、ハロゲン原子、炭素数
1〜12のアルキル基、ニトロ基、トリフルオロメチル
基等がある。その例として、ヒドロキシフェニル基、ア
ルコキシフェニル基(例えば、メトキシフェニル基、エ
トキシフェニル基等)、シアノフェニル基、アミノフェ
ニル基、(アルキルアご))フェニル基(例えば、(メ
チルアご〕)フェニル基、(エチルアξ))フェニル基
等)、(ジアルキルアミノ)フェニル基(例えば、(ジ
メチルアミノ)フェニル基、(ジエチルアミン)フェニ
ル基等)、ハロケノフェニル基(例えば、フルオロフェ
ニル基、クロロフェニル基、ブロモフェニル基等)、ア
ルキルフェニル基、(例えば、トリル基、エチルフェニ
ル基、クメニル基、キシリル基、メシチル基等)、ニト
ロフェニル基、トリフルオロメチルフェニル基、及びこ
れらの置換基(互いに同しでも異なっても良い。)を2
個または3個を有するフェニル基をあげることができる
。ただし置換基の位置は任意である。When R1 is a substituted group, examples of the substituent include a hydroxy group, an alkokene group having 1 to 12 carbon atoms, a cyano group, an amino group, an alkylamino group having 1 to 12 carbon atoms, and an alkylamino group having 1 to 12 carbon atoms.
Examples thereof include a dialkylamino group having two alkyl groups having 12 carbon atoms, an aro-ruazo group having 6 to 12 carbon atoms, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a nitro group, and a trifluoromethyl group. Examples thereof include hydroxyphenyl group, alkoxyphenyl group (e.g., methoxyphenyl group, ethoxyphenyl group, etc.), cyanophenyl group, aminophenyl group, phenyl group (e.g., (methylago)), (ethyl aξ)) phenyl group, etc.), (dialkylamino) phenyl group (e.g., (dimethylamino) phenyl group, (diethylamine) phenyl group, etc.), halochenophenyl group (e.g., fluorophenyl group, chlorophenyl group, bromophenyl group), groups), alkylphenyl groups (e.g., tolyl, ethylphenyl, cumenyl, xylyl, mesityl, etc.), nitrophenyl, trifluoromethylphenyl, and their substituents (same or different) 2)
Examples include phenyl groups having 1 or 3 phenyl groups. However, the position of the substituent is arbitrary.
R2としては水素原子、炭素数1〜6の低級アルキル基
、カルバモイル基、カルボキシル基、炭素数1〜12の
アルコキシ基を有するアルコキシカルボニル基、炭素数
6〜20のアリールオキシ基を有するアリールオキシカ
ルボニル基及び置換または無置換のアミン基が好ましい
。R2 is a hydrogen atom, a lower alkyl group having 1 to 6 carbon atoms, a carbamoyl group, a carboxyl group, an alkoxycarbonyl group having an alkoxy group having 1 to 12 carbon atoms, or an aryloxycarbonyl group having an aryloxy group having 6 to 20 carbon atoms. and substituted or unsubstituted amine groups are preferred.
R2が置換アごノ基の場合、その具体例としてメチルア
くノ基、エチルアミノ基、プロピルアごノ基、フェニル
アミノ基、トリルアミノ基、ヘンシルアくノ基、ジエチ
ルアミン基、ジフェニルアミノ基等をあげることができ
る。When R2 is a substituted agono group, specific examples thereof include a methylagono group, an ethylamino group, a propylagono group, a phenylamino group, a tolylamino group, a hensylagono group, a diethylamine group, a diphenylamino group, etc. I can do it.
R2が低級アルキル基の場合、その具体例としてメチル
基、エチル基、プロピル基、7゛チル基、イソプロピル
基、イソブチル基、等があげられる。When R2 is a lower alkyl group, specific examples include a methyl group, an ethyl group, a propyl group, a 7-ethyl group, an isopropyl group, an isobutyl group, and the like.
R2がアルコキシカルボニル基の場合、その具体例とし
てメトキシカルボニル基、エトキシカルボニル基、プロ
ポキシカルボニル基、ブトキンカルボニル基、イソプロ
ポキシカルボニル基、ヘンシルオキシカルボニル基など
があげられる。When R2 is an alkoxycarbonyl group, specific examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butquincarbonyl group, an isopropoxycarbonyl group, a hensyloxycarbonyl group, and the like.
R2がアリールオキシカルボニル基の場合、その具体例
として、フェノキシカルボニル基、ドルオキソカルボニ
ル基等があげられる。When R2 is an aryloxycarbonyl group, specific examples thereof include a phenoxycarbonyl group, a doloxocarbonyl group, and the like.
R3としては、炭素数l〜20のアルキル基、フェニル
基、ナフチル基等の芳香族炭素環基、ジヘンゾフラニル
基、カルバゾリル基、ジヘンゾ力ルハゾリル基等の芳香
族複素環基またはこれらの置換体が好ましい。R3 is preferably an alkyl group having 1 to 20 carbon atoms, an aromatic carbocyclic group such as a phenyl group or a naphthyl group, an aromatic heterocyclic group such as a dihenzofuranyl group, a carbazolyl group, a dihenzol hazolyl group, or a substituent thereof. .
R3が置換または無置換のアルキル基の場合、その具体
例としてはそれぞれ前述のR’における置換または無置
換のアルキル基の具体例と同し基をあげることができる
。When R3 is a substituted or unsubstituted alkyl group, specific examples include the same groups as the above-mentioned specific examples of the substituted or unsubstituted alkyl group for R'.
R3が置換基を有する芳香族炭素環基または置換基を有
する芳香族複素環基の場合、置換基の具体例としてはヒ
ドロキシ基、シアノ基、ニトロ基、ハロゲン原子(例え
ば、弗素原子、塩素原子、臭素原子等)、炭素数1〜1
2のアルキル基(例えば、メチル基、エチル基、プロピ
ル基、イソプロピル基等)、炭素数1〜12のアルコキ
シ基(例えば、メトキシ基、エトキシ基、プロポキン基
、ブトキシ基、ペンチルオキシ基、イソプロポキシ基、
イソブトキシ基、イソプロポキシ基、ter tブトキ
シ基、ネオペンチルオキシ基等)、トリフルオロメチル
基、トリメチルシリル基、メタンスルホニル基、アミノ
基、炭素数1〜12のアルキルアくノ基(例えば、メチ
ルア旦)基、エチルアくノ基、プロピルアミノ基等)、
炭素数1〜12のジアルキルアミノ基(例えば、ジメチ
ルアミノ基、ジエチルアミノ基、N−メチル−N−エチ
ルア旦)基等)、炭素数6〜12のアリールアミノ基(
例えば、フェニルア旦)基、トリルアミノ基等〉、炭素
数6〜15のアリール基を2個有するジアリールアミノ
基(例えば、ジフェニルアミノ基等)、炭素数6〜12
のアリールアゾ基(例えば、フェニルアゾ基、クロロフ
ェニルアゾ基・フルオロフェニルアゾ基、プロモフェニ
ルアソ基、シアノフェニルアゾ基、エトキシカルボニル
フェニルアゾ基、ニトロフェニルアゾ基、アセトアミド
フェニルアゾ基、メトキシフェニルアゾ基、メカルボキ
シル基、炭素数1−18のアルコキン基を有するアルコ
キシカルボニル基(例えぽメトキシカルボニル基、エト
キシカルボニル基等)、炭素数6〜16のアリールオキ
シ基を有するアリールオキシカルボニル基(例えばフユ
ノキシカルボニル基、ナフトキシカルボニル基等)、ア
ルカリ金属カルボキシラド基(アルカリ金属陽イオンの
例、Na@、KΦ、L i @等〉、アルカリ金属スル
ホナト基(アルカリ金属陽イオンの例、Na0に@、L
i’等)、アルキルカルボニル基(例えば、アセチル基
、プロピオニル基、ヘンシルカルボニル基等)、炭素数
6〜12のアリール基を有する了り−ルカルポニル基(
例えば、ベンゾイル基、トルオイル基等)、炭素数1〜
12のアルキルチオ基(例えば、メチルチオ基、エチル
チオ基等)、または炭素数1〜12のアリールチオ基(
例えば、フェニルチオ基、トリルチオ基等)をあげるこ
とができ、置換基の個数は工ないし5個であり、複数の
置換基が結合している場合にはそれらは互いに同しでも
異なってもよく、また置換基の結合位置は任意である。When R3 is an aromatic carbocyclic group having a substituent or an aromatic heterocyclic group having a substituent, specific examples of the substituent include a hydroxy group, a cyano group, a nitro group, a halogen atom (e.g., a fluorine atom, a chlorine atom, , bromine atom, etc.), carbon number 1-1
2 alkyl groups (e.g., methyl group, ethyl group, propyl group, isopropyl group, etc.), alkoxy groups having 1 to 12 carbon atoms (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, isopropoxy group) basis,
isobutoxy group, isopropoxy group, tert-butoxy group, neopentyloxy group, etc.), trifluoromethyl group, trimethylsilyl group, methanesulfonyl group, amino group, alkyl akuno group having 1 to 12 carbon atoms (e.g., methyl adan) group, ethylamino group, propylamino group, etc.),
dialkylamino group having 1 to 12 carbon atoms (e.g., dimethylamino group, diethylamino group, N-methyl-N-ethylamino group, etc.), arylamino group having 6 to 12 carbon atoms (
For example, phenylamino group, tolylamino group, etc.), diarylamino group having two aryl groups having 6 to 15 carbon atoms (e.g. diphenylamino group, etc.), 6 to 12 carbon atoms
arylazo groups (e.g., phenylazo group, chlorophenylazo group/fluorophenylazo group, promophenylazo group, cyanophenylazo group, ethoxycarbonylphenylazo group, nitrophenylazo group, acetamidophenylazo group, methoxyphenylazo group, A carboxyl group, an alkoxycarbonyl group having an alkoxy group having 1 to 18 carbon atoms (e.g. methoxycarbonyl group, ethoxycarbonyl group, etc.), an aryloxycarbonyl group having an aryloxy group having 6 to 16 carbon atoms (e.g. fuunoxycarbonyl) groups, naphthoxycarbonyl groups, etc.), alkali metal carboxylad groups (examples of alkali metal cations, Na@, KΦ, Li@, etc.), alkali metal sulfonato groups (examples of alkali metal cations, Na0@, L
i', etc.), an alkylcarbonyl group (e.g., acetyl group, propionyl group, hensylcarbonyl group, etc.), an arylcarbonyl group having an aryl group having 6 to 12 carbon atoms (
For example, benzoyl group, toluoyl group, etc.), carbon number 1-
12 alkylthio groups (e.g., methylthio group, ethylthio group, etc.), or arylthio groups having 1 to 12 carbon atoms (
For example, phenylthio group, tolylthio group, etc.), the number of substituents is from 1 to 5, and when multiple substituents are bonded, they may be the same or different from each other, Further, the bonding position of the substituent is arbitrary.
R4としては、水素原子もしくはmfkのR3の具体例
と同し基をあげることができる。Examples of R4 include a hydrogen atom or the same group as the specific example of R3 in mfk.
Yが無置換の複素5員環または複素6員環を表す場合、
具体例として、インダゾール環、オキサゾール環、チア
ゾール環、ヘンゾイミダヅール環、ヘンジチアゾール環
、ヘンゾオキサヅール環、ピリミジン環、ペリミジン環
等をあげることができる。When Y represents an unsubstituted 5-membered heterocyclic ring or a 6-membered heterocyclic ring,
Specific examples include an indazole ring, an oxazole ring, a thiazole ring, a henzimidazur ring, a hendithiazole ring, a henzoxadur ring, a pyrimidine ring, and a perimidine ring.
Yが置換基を有する複素5員環または複素6員環を表す
場合、置換基の具体例としては、前述のR3が置換基を
有する芳香族炭素環基の場合の置換基の具体例と同し基
をあげることができる。When Y represents a 5-membered heterocyclic ring or a 6-membered heterocyclic ring having a substituent, specific examples of the substituent are the same as the above-mentioned specific examples of the substituent when R3 is an aromatic carbocyclic group having a substituent. I can give you a foundation.
)I
40
ナフタレン環の3位〜8位の任意の位置に置換すること
が可能であるが、8位に置換することが好ましい。) I 40 Although it is possible to substitute at any position from the 3rd to the 8th position of the naphthalene ring, the substitution at the 8th position is preferable.
Bは芳香族炭化水素の2価基、または窒素原子を環内に
含む複素環の2価基を表し、これらはいずれもアルキル
基、ハロゲン原子、ニトロ基、トリフルオロメチル基、
シアノ基またはヒドロキシ基等で置換されても良い。芳
香族炭化水素の2価基としては、0−フェニレン基、0
−ナフチレン基、peri−ナフチレン基、1,2−ア
ントラキノニレン基、9.10−フエナントリレン基等
を挙げることができる。また窒素原子を環内に含む複素
環の2価基としては例えば、3,4−ピラゾールシリル
基、2,3−ピリジイル基、4,5−ピリミジンジイル
基、6,7−インダゾールジイル基、5,6−ベンズイ
ミダゾールジイル基、6゜7−キラリンジイル基等を挙
げることができる。B represents an aromatic hydrocarbon divalent group or a heterocyclic divalent group containing a nitrogen atom in the ring, and these are all alkyl groups, halogen atoms, nitro groups, trifluoromethyl groups,
It may be substituted with a cyano group, a hydroxy group, or the like. Divalent groups of aromatic hydrocarbons include 0-phenylene group, 0
Examples include -naphthylene group, peri-naphthylene group, 1,2-anthraquinonylene group, and 9,10-phenanthrylene group. Examples of heterocyclic divalent groups containing a nitrogen atom in the ring include 3,4-pyrazolesilyl group, 2,3-pyridiyl group, 4,5-pyrimidinediyl group, 6,7-indazolediyl group, , 6-benzimidazolediyl group, and 6°7-chiralindiyl group.
つぎに本発明のジスアゾ化合物を具体例を第1表に挙げ
るが、本発明はこれによって限定されるものではない。Next, specific examples of the disazo compounds of the present invention are listed in Table 1, but the present invention is not limited thereto.
下記一般式〔1゛〕で示されるジスアゾ化合物の具体例
中のCp’ は第2表、第3表もしくは第4表で示され
るカプラー残基を表す。Cp' in specific examples of the disazo compound represented by the following general formula [1] represents a coupler residue shown in Table 2, Table 3 or Table 4.
1
一般式〔1゛
〕
Cp゛
N=N−Ar2−C=C−八rl
C−C−Ar3−N=N−Cp
5 R6
2
第2表
27
第2表
(続き)
第2表
(続き)
第2表
(続き)
第2表(続き)
第2表
(続き)
第2表
(続き)
3
第2表
(続き)
第2表
(vLき)
第2表
(@き)
第4表
第4表(続き)
第4表
(続き)
5
第4表
(続き)
第4表
(続き)
7
第4表
(続き)
第4表(続き)
第4表(絖き)
第4表
(続き)
本発明の新規なジスアゾ化合物は下記の方法により容易
に合成することができる。即ち一般式〔2〕で示される
ジアミノ化合物を常法によりテトラアゾ化し、アルカリ
の存在下対応するカプラーとカップリングさせるか、あ
るいはテトラゾニウム塩をホウフッ化塩や塩化亜鉛複塩
などの形で単離した後、N、 N−ジメチルホルムア
ミド、ジメチルスルホキシド等の溶媒中でアルカリの存
在下にカプラーとカップリングさせることにより容易に
合成することができる。1 General formula [1゛] Cp゛N=N-Ar2-C=C-8rl C-C-Ar3-N=N-Cp 5 R6 2 Table 2 27 Table 2 (continued) Table 2 (continued) ) Table 2 (continued) Table 2 (continued) Table 2 (continued) Table 2 (continued) 3 Table 2 (continued) Table 2 (vL) Table 2 (@ki) Table 4 Table 4 (continued) Table 4 (continued) 5 Table 4 (continued) Table 4 (continued) 7 Table 4 (continued) Table 4 (continued) Table 4 (continued) Table 4 (continued) The novel disazo compound of the present invention can be easily synthesized by the following method. That is, the diamino compound represented by the general formula [2] was tetraazotized by a conventional method and coupled with the corresponding coupler in the presence of an alkali, or the tetrazonium salt was isolated in the form of a borofluoride salt, zinc chloride double salt, etc. After that, it can be easily synthesized by coupling with a coupler in a solvent such as N,N-dimethylformamide or dimethylsulfoxide in the presence of an alkali.
H2N−Ar2−C=C−Ar’−C=C−Ar3−N
H2C2〕R5R1!
但しAr1、Ar2、Ar3、R5及びR11は前記一
般式〔1〕のArl、Ar2、Ar3R5及びR6と同
じ意味を表す。H2N-Ar2-C=C-Ar'-C=C-Ar3-N
H2C2]R5R1! However, Ar1, Ar2, Ar3, R5 and R11 have the same meanings as Arl, Ar2, Ar3R5 and R6 in the general formula [1].
合成例
(第1表の化合物群(1)でカプラーが(Cp21)で
あるジスアゾ化合物の合成)
下記構造式〔3〕で表されるジアミノ化合物3゜2
12g (0,01mol )を濃塩酸25−及び水3
0dから調製した希塩酸に加えて60℃の水溶上で約3
0分間攪拌した。次にこの混合物をOoCに冷却し、そ
れに亜硝酸ナトリウム1.52gを水57nlに溶解し
た溶液をOoCで約20分間かけて滴下した。その後同
温度で1時間攪拌し、少量の未反応物を濾別した後、濾
液を別の容器に調製したカプラー(Cp’−21)7.
65g (0,02mol ) 、酢酸ナトリウム3.
28g、水20−とDMF 300−からなる溶液に、
水冷下、攪拌しながら滴下した。その後室温で2時間攪
拌した後、生成した結晶を濾取し、水洗い、アセトン洗
いを繰り返し行い精製した。9.1gのジスアゾ化合物
の黒粉末が得られた。収率83%。分解温度270℃以
上。Synthesis Example (Synthesis of a disazo compound whose coupler is (Cp21) in Compound Group (1) in Table 1) 12 g (0.01 mol) of a diamino compound represented by the following structural formula [3] was dissolved in concentrated hydrochloric acid 25 - and water 3
In addition to dilute hydrochloric acid prepared from 0d, about 3
Stirred for 0 minutes. Next, this mixture was cooled to OoC, and a solution of 1.52 g of sodium nitrite dissolved in 57 nl of water was added dropwise thereto over about 20 minutes at OoC. Thereafter, the coupler (Cp'-21) was stirred at the same temperature for 1 hour, a small amount of unreacted material was filtered off, and the filtrate was prepared in a separate container.7.
65g (0.02mol), sodium acetate3.
28 g, in a solution consisting of 20 - of water and 300 - of DMF,
It was added dropwise while stirring under water cooling. After stirring at room temperature for 2 hours, the formed crystals were collected by filtration and purified by repeated washing with water and acetone. 9.1 g of black powder of disazo compound was obtained. Yield 83%. Decomposition temperature 270℃ or higher.
元素分析値 C7oH48N806として計算値 C7
6,63X H4,41X N10.21%実測
値 C76、36% H4,48X N10.03
%本発明の電子写真感光体は前記一般式〔1〕で表され
るジスアゾ化合物を1種または2種含有する電子写真感
光層を有する。各種の形態の電子写真感光体が知られて
いるが、本発明の電子写真感光体はその何れのタイプの
感光体であっても良いが通常次に示す(I)、(n)ま
たは(III)のタイプの電子写真感光体構造を持つ。Elemental analysis value Calculated value as C7oH48N806 C7
6,63X H4,41X N10.21% Actual value C76, 36% H4,48X N10.03
% The electrophotographic photoreceptor of the present invention has an electrophotographic photosensitive layer containing one or two types of disazo compounds represented by the above general formula [1]. Various forms of electrophotographic photoreceptors are known, and the electrophotographic photoreceptor of the present invention may be any type of photoreceptor, but it is usually one of the following types (I), (n), or (III). ) type of electrophotographic photoreceptor structure.
(I)導電性支持体上にジスアゾ化合物をバインダーあ
るいは電荷担体輸送媒体中に分散させてなる電子写真感
光層を設けたもの。(I) An electrophotographic photosensitive layer comprising a disazo compound dispersed in a binder or a charge carrier transport medium is provided on a conductive support.
(II)導電性支持体上にジスアゾ化合物を主成分とす
る電荷担体発生層を設け、その上に電荷担体輸送層を設
けたもの。(II) A charge carrier generation layer containing a disazo compound as a main component is provided on a conductive support, and a charge carrier transport layer is provided thereon.
(III)導電性支持体上に電荷担体輸送層を設け、そ
の上にジスアゾ化合物を主成分とする電荷担体発生層を
設けたもの。(III) A charge carrier transport layer is provided on a conductive support, and a charge carrier generation layer containing a disazo compound as a main component is provided thereon.
本発明のジスアゾ化合物は光を吸収すると極めて高い効
率で電荷担体を発生する作用を持つ。発生した電荷担体
は、電荷担体輸送化合物によって輸送される。The disazo compound of the present invention has the ability to generate charge carriers with extremely high efficiency when it absorbs light. The generated charge carriers are transported by a charge carrier transport compound.
タイプ(I)の電子写真感光体を作製するにはジスアゾ
化合物の微粒子をバインダー溶液もしくは電荷担体輸送
化合物とバインダー溶液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した後、乾燥すれば良い
。このときの電子写真感光層の厚さは3〜30μ、好ま
しくは5〜20μが良い。To prepare a type (I) electrophotographic photoreceptor, fine particles of a disazo compound are dispersed in a binder solution or a solution containing a charge carrier transport compound and a binder solution, and this is coated on a conductive support. Just dry it. The thickness of the electrophotographic photosensitive layer at this time is preferably 3 to 30 microns, preferably 5 to 20 microns.
タイプ(II)の感光体を作製するには、導電性支持体
上にジスアゾ化合物を真空蒸着して電荷担体発生層を形
成するか、ジスアゾ化合物の微粒子を、バインダー樹脂
を溶解した適当な溶媒中に分散して得られた分散液を塗
布、乾燥して電荷担体発生層を形成し、更に必要があれ
ば、例えばパフ研磨などの方法によって表面仕上げをす
るか、膜厚を調整した後、その上に電荷担体輸送物質及
びバインダー樹脂を含む溶液を塗布、乾燥して得られる
。この時の電荷担体発生層の厚みは0.01μ〜4μ、
好ましくは0.1μ〜2μが良く、電荷担体輸送層の厚
みは3μ〜30μ、好ましくは5μ〜20μがよい。To prepare a type (II) photoreceptor, a disazo compound is vacuum-deposited on a conductive support to form a charge carrier generation layer, or fine particles of a disazo compound are deposited in a suitable solvent in which a binder resin is dissolved. The resulting dispersion is coated and dried to form a charge carrier generation layer, and if necessary, the surface is finished by a method such as puff polishing or the film thickness is adjusted, and then It is obtained by coating a solution containing a charge carrier transporting substance and a binder resin thereon and drying it. The thickness of the charge carrier generation layer at this time is 0.01μ to 4μ,
The thickness of the charge carrier transport layer is preferably 3 to 30 microns, preferably 5 to 20 microns.
タイプ(I[)の電子写真感光体はタイプ(II)の電
子写真感光体の積層順序を逆にすることにより作製でき
る。The type (I[) electrophotographic photoreceptor can be produced by reversing the stacking order of the type (II) electrophotographic photoreceptor.
(I)、(II)及び(III)のタイプの感光体で用
いられるジスアゾ化合物はボールミル、サンドミル、振
動ミル等の分散機により粒径0,1μ〜2μ、好ましく
は0.3μ〜2μに分散して用いられる。The disazo compound used in photoreceptors of types (I), (II) and (III) is dispersed to a particle size of 0.1μ to 2μ, preferably 0.3μ to 2μ, using a dispersing machine such as a ball mill, sand mill, or vibration mill. It is used as
タイプ(I)の電子写真感光体において使用されるジス
アゾ化合物の量は少なすぎると感度が悪く、多すぎると
帯電性が悪くなったり、電子写真感光層の膜強度が悪く
なったりし、電子写真感光層中のジスアゾ化合物の占め
る割合は、バインダーを用いる場合、バインターに対し
0..01〜2重量倍、好ましくは0.05〜1重量倍
がよく、電荷担体輸送化合物の割合はバインダーに対し
0゜1〜2重量倍、好ましくは0.3〜1. 5重量倍
の範囲がよい。またそれ自身バインダーとして使用でき
る電荷担体輸送化合物の場合には、ジスアゾ化合物の添
加量は電荷担体輸送化合物に対し0゜6
01〜0.5重量倍使用するのが好ましい。If the amount of the disazo compound used in the type (I) electrophotographic photoreceptor is too small, the sensitivity will be poor, and if it is too large, the charging property will be poor, the film strength of the electrophotographic photosensitive layer will be poor, and the electrophotographic When a binder is used, the proportion of the disazo compound in the photosensitive layer is 0.0% to the binder. .. The ratio of the charge carrier transport compound to the binder is 0.1 to 2 times by weight, preferably 0.05 to 1 times by weight, preferably 0.3 to 1 times by weight. A range of 5 times the weight is preferable. In the case of a charge carrier transporting compound which itself can be used as a binder, the amount of the disazo compound added is preferably 0.6 to 0.5 times the weight of the charge carrier transporting compound.
またタイプ(II)及び(I)の電子写真感光体におい
て電荷担体発生化合物含有層となるジスアゾ化合物含有
層を塗布形成する場合、バインダーに対するジスアゾ化
合物の使用量は0.1重量倍以上が好ましく、それ以下
だと十分な感度が得られない。またバインダーは無くと
も使用できる。In addition, when forming a disazo compound-containing layer which becomes a charge carrier generating compound-containing layer in type (II) and (I) electrophotographic photoreceptors, the amount of disazo compound used is preferably at least 0.1 times the weight of the binder; If it is less than that, sufficient sensitivity cannot be obtained. It can also be used without a binder.
電荷担体輸送化合物含有層中の電荷担体輸送化合物の割
合は、バインダーに対し0. 2〜2重量倍、好ましく
は0. 3〜1.5重量倍が好ましい。それ自身バイン
ダーとして使用できる高分子電荷担体輸送化合物を使用
する場合は、他のバインダーは無くとも使用できる。The ratio of the charge carrier transport compound in the charge carrier transport compound-containing layer to the binder is 0. 2 to 2 times by weight, preferably 0. 3 to 1.5 times by weight is preferred. If a polymeric charge carrier transport compound is used which itself can be used as a binder, no other binder can be used.
本発明の電子写真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、亜鉛などの金属板、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、酸化インジウム、酸化スズ、
ヨウ化銅等の導電材料を蒸着、もしくは分散塗布したも
の、あるいは7
塩化ナトリウム、塩化カルシウム等の無機塩や有機四級
アンモニウム塩により導電処理した祇などが使用される
。The conductive support used in the electrophotographic photoreceptor of the present invention includes a metal plate made of aluminum, copper, zinc, etc., a plastic sheet or plastic film made of polyester, aluminum, indium oxide, tin oxide, etc.
Used are those coated with a conductive material such as copper iodide by vapor deposition or dispersion, or conductive treated with an inorganic salt such as sodium chloride or calcium chloride, or an organic quaternary ammonium salt.
バインダーが用いられる場合のバインダーとしては疎水
性で、かつ誘電率が高く、電気絶縁性のフィルム形成性
高分子重合体を用いるのが好ましい。この様な高分子重
合体としては例えば次のものをあげることができるが勿
論これらに限定されるものではない。When a binder is used, 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.
ポリカーボネート、ポリエステル、ポリエステルカーボ
ネート、ポリスルポン、メタクリル樹脂、アクリル樹脂
、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリスチレン
、ポリビニルアセテート、スチレン−ブタジェン共重合
体、塩化ビニリデンアクリロニトリル共重合体、塩化ビ
ニル−#酸ヒニル共重合体、塩化ビニル−酢酸ビニル−
無水マレイン酸共重合体、シリコンオイル、シリコン−
アルキッド樹脂、フェノール−ホルムアルデヒド樹脂、
スチレン−アルキッド樹脂、スチレン−無水マレイン酸
共重合体、フェノキシ樹脂、ポリビニルブチラール樹脂
、ポリ−N−ビニルカルバゾール。Polycarbonate, polyester, polyester carbonate, polysulfone, methacrylic resin, acrylic resin, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, styrene-butadiene copolymer, vinylidene chloride acrylonitrile copolymer, vinyl chloride-hinyl chloride copolymer Combination, vinyl chloride-vinyl acetate-
Maleic anhydride copolymer, silicone oil, silicone
Alkyd resin, phenol-formaldehyde resin,
Styrene-alkyd resin, styrene-maleic anhydride copolymer, phenoxy resin, polyvinyl butyral resin, poly-N-vinylcarbazole.
これらの樹脂バインダーは、単独であるいは2種以上の
混合物として用いることができる。These resin binders can be used alone or as a mixture of two or more.
本発明の感光体において可塑剤を樹脂バインダーと混合
して用いることができる。In the photoreceptor of the present invention, a plasticizer can be used in combination with a resin binder.
可塑剤としてはビフェニル、塩化ビフェニル、0−テル
フェニル、p−テルフェニル、チブチルフタレート、ジ
メチルグリコールツクレート、ジオクチルフタレート、
トリフェニル燐酸、塩素化パラフィン、ジウラリルチオ
ジプロビオネート等があげられる。Plasticizers include biphenyl, chlorinated biphenyl, 0-terphenyl, p-terphenyl, thibutyl phthalate, dimethyl glycol tuclate, dioctyl phthalate,
Examples include triphenyl phosphoric acid, chlorinated paraffin, diuralyl thiodiprobionate, and the like.
本発明の電子写真感光体を作製する場合、感光層中に増
感剤などの添加剤を使用しても良い。When producing the electrophotographic photoreceptor of the present invention, additives such as a sensitizer may be used in the photosensitive layer.
増感剤としては、ブリリアントグリーン、ビクメタン染
料、ローダミンB10−ダミン6G、ロータミンGエキ
ストラ、エオシンs1エリトロシン、ローズヘンガル、
フルオレセイン等のキシンテン染料、メチレンブルー等
のチアジン染料、C11、Ba5ic、Violet7
(C,I、48020)等のアストラゾン染料、シア
ニン染料、2.6−ジフェニル−4−(N、N−ジメチ
ルアミノフェニル)チアピリリウムペルクロレート、ベ
ンゾビリリウム塩(特公昭48−2s、658号公報記
載)等のピリリウム染料をあげることができる。Sensitizers include brilliant green, bicumethane dye, rhodamine B10-damine 6G, rotamine G extra, eosin s1 erythrosine, rose hengal,
Xinten dyes such as fluorescein, thiazine dyes such as methylene blue, C11, Ba5ic, Violet7
Astrazone dyes such as (C, I, 48020), cyanine dyes, 2,6-diphenyl-4-(N,N-dimethylaminophenyl)thiapyrylium perchlorate, benzobyrylium salts (Japanese Patent Publication No. 48-2s, 658 Examples of pyrylium dyes include pyrylium dyes such as Pyrylium dyes (described in Japanese Patent Publication No.
また、電子写真感光体の表面性をよくするために、シリ
コンオイル、フッ素系界面活性剤等を使用することがで
きる。Further, in order to improve the surface properties of the electrophotographic photoreceptor, silicone oil, fluorine-based surfactant, etc. can be used.
本発明において電荷担体輸送層に用いられる電荷担体輸
送物質としては、電子を輸送する化合物と正孔を輸送す
る化合物の2種類に分類される。In the present invention, charge carrier transport materials used in the charge carrier transport layer are classified into two types: compounds that transport electrons and compounds that transport holes.
本発明の電子写真感光体には両者とも使用子ることがで
きる。Both can be used in the electrophotographic photoreceptor of the present invention.
電子を輸送する化合物としては電子吸引性基を有する化
合物、例えば2,4,7.−)ジニトロ9−フルオレノ
ン、2,4,5.7−テトラニトロ−9−フルオレノン
、9−ジシアノメチレン2.4.7−トリニトロフルオ
レノン、9−ジシアノメチレン−2,4,5,7−チト
ラニトロフルオレノン、テトラニトロ力ルハヅール、ク
ロラニル、2,3−ジクロlニア−5,6−ジンアツヘ
ンゾキノン、2.4.7−1−リニトロ−9,1゜フェ
ナントレンキノン、テトラクロロ無水フタル酸、テラシ
アノエチレン、テトラシアノキノジメタン等をあげるこ
とができる。Compounds that transport electrons include compounds having an electron-withdrawing group, such as 2, 4, 7. -) dinitro 9-fluorenone, 2,4,5.7-tetranitro-9-fluorenone, 9-dicyanomethylene 2.4.7-trinitrofluorenone, 9-dicyanomethylene-2,4,5,7-titranitro Fluorenone, tetranitrohydrazur, chloranil, 2,3-dichloro-5,6-diaminezoquinone, 2.4.7-1-linitro-9,1゜phenanthrenequinone, tetrachlorophthalic anhydride, terracyano Ethylene, tetracyanoquinodimethane, etc. can be mentioned.
正孔を輸送する化合物としては、電子供与性基を有する
化合物、例えば高分子の物では、(al 特公昭34
−10,966号公報記載のポリビニルカルバゾール及
びその誘導体、
Cb)特公昭4118.674号、同43−19192
号公報記載のポリビニルピレン、ポリビニルアントラセ
ン、ポリ−2−ビニル−4−(4’ジメチルア旦ノフエ
ニル)−5−フェニルオキサゾール、ポリ−3−ビニル
−N−エチルカルバソール等のビニル重合体、
(Cl 特公昭43−1’9,193号公報記載のポ
リアセナフチレン、ポリインデン、アセナフチレンとス
チレンの共重合体等の重合体、
(di 特公昭56−13.940号公報などに記載
のピレン−ホルムアルデヒド樹脂、ブロムピレンホルム
アルデヒド樹脂、エチルカルバゾールホルムアルデヒド
樹脂等の縮合樹脂、
(el 特開昭56−90.883号、同56−16
1.550号公報に記載された各種のトリフェニルメタ
ンポリマー
また低分子のものでは、
(fl 米国特許第3..112,197号明細書な
どに記載されているトリアゾール誘導体、(gl 米
国特許第3,189,4.47号明細書などに記載され
ているオキサジアゾール誘導体、(hl 特公昭37
−16.096号公報などに記載されているイミダゾー
ル誘導体、
(1)米国特許第3.615,402号、同3,820
.989号、同3,542.544号、特公昭45−5
55号、同51−10,983号、特開昭51−93,
224号、同55−1(18,667号、同55−15
6953号、同56−3665.6号明細書、公報など
に記載のポリアリールアルカン誘導体、
(jl 米国特許第3,180,729号、同4.2
78.746号、特開昭55−88,064号、同55
−88,065号、同49−105,537号、同55
−51.086号、同56−80゜051号、同56−
88,141号、同57−45.545号、同54−1
12,637号、同55−74.546号明細書、公報
などに記載されているピラゾロン誘導体及びピラゾロン
誘導体、cK)米国特許第3,615.404号、特公
昭51−10,105号、同46−3.712号、同4
7−28,336号、特開昭54−83.435号、同
54−110,836号、同54−119.925号明
細書、公報などに記載されているフェニレンシア旦ン誘
導体、
(1)米国特許第3.56L 450号、同3,18
0.703号、同3,240,597号、同3゜658
.520号、同4,232,103号、同4.175,
961号、同4,012,376号、***国特許(DA
S)1.110,518号、特公昭49−35,702
号、同39−27.577号、特開昭55−144,2
50号、同56119.132号、同56−22.43
7号明細書、公報などに記載されているアリールア旦ン
誘導体、
(m) 米国特許第3,526,501号明細書記載
のア旦ノ置換カルコン誘導体、
fnl 米国特許第3,542,546号明細書など
に記載のN、N−ジカルバジル誘導体、(0)米国特許
第3,257,203号明細書などに記載のオキサゾー
ル誘導体、
(pl 特開昭56−46,234号公報などに記載
のスチリルアントラセン誘導体、
(ql 特開昭54−110,837号公報等に記載
されているフルオレノン誘導体、
(rl 米国特許第3.717.462号、特開昭5
4−59,143号(米国特許第4.150,987号
に対応)、同55−52,063号、同55−52.0
64号、同55−46.760号、同55−85.49
5号、同57−11.350号、同57−148.74
9号、同57−104144号明細書、公報などに記載
されているヒドラゾン講導体、
(S) 米国特許第4.04.7.948号、同4,
047.949号、同4,265,990号、同427
3.84.6号、同4.299,897号、同4.30
6,008号明細書などに記載のヘンジジン講導体、
(tl 特開昭58−190,953号、同59−9
5.540号、同59−97,148号、同59195
.658号、同62−36.674号公報などに記載さ
れているスチルヘン講導体等がある。Compounds that transport holes include compounds having an electron-donating group, such as polymer compounds (al.
Polyvinylcarbazole and its derivatives described in Japanese Patent Publication No. 10,966, Cb) Japanese Patent Publication No. 4118.674, No. 43-19192
Vinyl polymers such as polyvinylpyrene, polyvinylanthracene, poly-2-vinyl-4-(4'dimethylanandanophenyl)-5-phenyloxazole, and poly-3-vinyl-N-ethylcarbasol, (Cl Polymers such as polyacenaphthylene, polyindene, copolymers of acenaphthylene and styrene, etc., described in Japanese Patent Publication No. 43-1'9,193, pyrene-formaldehyde described in Japanese Patent Publication No. 56-13.940, etc. resin, condensation resin such as brompyrene formaldehyde resin, ethylcarbazole formaldehyde resin, (el JP-A-56-90.883, JP-A-56-16)
Among the various triphenylmethane polymers and low molecular weight ones described in JP 1.550, (fl triazole derivatives described in U.S. Pat. No. 3.112,197, etc.; Oxadiazole derivatives described in the specification of No. 3,189, 4.47 etc.
Imidazole derivatives described in -16.096, etc. (1) U.S. Patent Nos. 3,615,402 and 3,820;
.. No. 989, No. 3,542.544, Special Publication No. 1977-5
No. 55, No. 51-10,983, JP-A-51-93,
No. 224, No. 55-1 (No. 18,667, No. 55-15
Polyarylalkane derivatives described in U.S. Pat. No. 6953, U.S. Pat. No. 56-3665.6, publications, etc.
No. 78.746, JP-A-55-88,064, JP-A No. 55
-88,065, 49-105,537, 55
-51.086, 56-80゜051, 56-
No. 88,141, No. 57-45.545, No. 54-1
Pyrazolone derivatives and pyrazolone derivatives described in US Pat. No. 12,637, US Pat. 46-3.712, same 4
7-28,336, JP-A No. 54-83.435, JP-A No. 54-110,836, JP-A No. 54-119.925, publications, etc. ) U.S. Patent No. 3.56L 450, U.S. Patent No. 3,18
No. 0.703, No. 3,240,597, No. 3゜658
.. No. 520, No. 4,232,103, No. 4.175,
No. 961, No. 4,012,376, West German Patent (DA
S) No. 1.110,518, Special Publication No. 1973-35,702
No. 39-27.577, JP-A-55-144, 2
No. 50, No. 56119.132, No. 56-22.43
(m) Arylatanone derivatives described in US Pat. No. 7, publications, etc., (m) Amano-substituted chalcone derivatives described in US Pat. No. 3,526,501, fnl US Pat. No. 3,542,546. N,N-dicarbasyl derivatives described in the specifications, (0) oxazole derivatives described in U.S. Patent No. 3,257,203, etc., (pl) Styryl anthracene derivatives, (ql Fluorenone derivatives described in JP-A No. 54-110,837, etc., (rl U.S. Pat. No. 3,717,462, JP-A-Sho 5)
No. 4-59,143 (corresponding to U.S. Pat. No. 4,150,987), U.S. Pat. No. 55-52,063, U.S. Pat. No. 55-52.0
No. 64, No. 55-46.760, No. 55-85.49
No. 5, No. 57-11.350, No. 57-148.74
No. 9, US Pat. No. 57-104144, the hydrazone conductor described in the publication, (S) U.S. Pat. No. 4.04.7.948, No. 4,
No. 047.949, No. 4,265,990, No. 427
3.84.6, 4.299,897, 4.30
6,008 specification etc., (tl JP-A-58-190,953, JP-A-59-9)
No. 5.540, No. 59-97,148, No. 59195
.. There are the Stilchen conductors described in No. 658 and No. 62-36.674.
なお本発明において、電荷担体を輸送する化合物は(a
)〜(tlにあげられた化合物に限定されず、これまで
公知の全ての電荷担体輸送化合物を用いることができる
。In the present invention, the compound that transports charge carriers is (a
) to (tl), but all charge carrier transport compounds known to date can be used.
本発明の電子写真感光体を作製する場合、電荷発生層及
び電荷輸送層中に増感剤などの添加剤を添加して使用し
てもよい。また電荷発生層中に電荷輸送化合物を添加1
て使用してもよい。When producing the electrophotographic photoreceptor of the present invention, additives such as a sensitizer may be added to the charge generation layer and the charge transport layer. Additionally, a charge transport compound is added to the charge generation layer.
You may also use it.
増感剤としては、 ロラニル、テトラシアノエチレン、
メチルバイオレット、ローダミンB1シアニン染料1.
メロシアニン染料、ピリリウム染料、チアピリリウム染
料などがあげられる。Sensitizers include loranil, tetracyanoethylene,
Methyl violet, rhodamine B1 cyanine dye 1.
Examples include merocyanine dyes, pyrylium dyes, and thiapyrylium dyes.
なお、本発明の電子写真感光体には、導電性支持体と感
光層の間に、必要に応して接着層又はバリヤ層を設ける
ことができる。これらの層に用いられる材料としては、
前記樹脂バインダーに用いられるポリマーの他に、ゼラ
チン、カゼイン、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、特開昭51−84
..247号公報に記載の塩化ビニリデン系ポリマーラ
テックス、特開昭59−114.544号公報に記載の
スチレンーブクジエン系ポリマーラテックスまたは酸化
アルミニウム等がありこれらの層の厚さは1μm以下が
好ましい。In addition, in the electrophotographic photoreceptor of the present invention, an adhesive layer or a barrier layer can be provided between the conductive support and the photosensitive layer, if necessary. The materials used for these layers include:
In addition to the polymers used in the resin binder, gelatin, casein, polyvinyl alcohol, ethyl cellulose, carboxymethyl cellulose, and JP-A-51-84
.. .. Examples include vinylidene chloride polymer latex described in Japanese Patent Publication No. 247, styrene-bucdiene polymer latex or aluminum oxide described in JP-A-59-114.544, and the thickness of these layers is preferably 1 μm or less.
以上のようにして得られた感光体には更にレーザーのよ
うな干渉性光を露光に使用した場合に発生する干渉縞防
止策を必要に応して施すことができる。そのような技術
としては、特開昭60−186.850号記載の光散乱
反射面を有する下引き層の設置、特開昭60−184.
258号記載のチタンブラック含有下引き層の設置、特
開昭58−82,249号記載の電荷担体発生層で使用
光源の光の大部分を吸収させる方法、特開昭6118.
963号記載の電荷担体輸送層にミクロ相分離構造をと
らせる方法、特開昭60−86゜550号記載の光導電
層中に干渉性光を吸収または散乱する物質を混入する方
法、特開昭63−106.757号記載の感光体表面に
干渉性光の波長の1/4以上の深さを持つ凹部を設ける
方法、特開昭62−172.371号、特開昭62−1
74.771号記載の透明支持体の裏面に光散乱層ある
いは光吸収層を設ける方法等をあげることができる。The photoreceptor obtained as described above may be further provided with measures to prevent interference fringes that occur when coherent light such as a laser is used for exposure, if necessary. Such techniques include the installation of an undercoat layer having a light scattering and reflective surface as described in JP-A No. 60-186.850, and the method described in JP-A-60-184.
Installation of a titanium black-containing subbing layer as described in JP-A-58-82,249, a method of absorbing most of the light from a used light source with a charge carrier generation layer as described in JP-A-58-82,249, and JP-A-6118.
A method of causing a charge carrier transport layer to have a microphase separation structure as described in No. 963, a method of incorporating a substance that absorbs or scatters coherent light into a photoconductive layer as described in JP-A-60-86゜550; Method of providing a recessed portion having a depth of 1/4 or more of the wavelength of coherent light on the surface of a photoreceptor described in No. 1983-106.757, JP-A No. 62-172.371, JP-A No. 62-1
Examples include the method described in No. 74.771, in which a light scattering layer or a light absorption layer is provided on the back side of a transparent support.
以上本発明の電子写真感光体について詳細に説明したが
、本発明の電子写真感光体は一般に感度が高く、繰り返
し使用時の電子写真特性の変化が小さい特徴を有してい
る。The electrophotographic photoreceptor of the present invention has been described in detail above, and the electrophotographic photoreceptor of the present invention is generally characterized by high sensitivity and little change in electrophotographic characteristics upon repeated use.
本発明の電子写真感光体は電子写真複写機の他レーザー
、ブラウン管、LED等を光源とするプリンターの感光
体などの分野に広く応用することができる。The electrophotographic photoreceptor of the present invention can be widely applied to photoreceptors for printers using lasers, cathode ray tubes, LEDs, etc. as light sources in addition to electrophotographic copying machines.
本発明のジスアゾ化合物を含む光導電性組成物はビデオ
カメラの撮像管の光導電層として、また信号転送や走査
を行う一次元または二次元配列された半導体回路上の全
面に設けた受光層(光導電層)を有する固体撮像素子の
光導電層として用いることかできる。また、八、に、G
hosh、 Tom Feng。The photoconductive composition containing the disazo compound of the present invention can be used as a photoconductive layer in the image pickup tube of a video camera, or as a light-receiving layer ( It can be used as a photoconductive layer of a solid-state image sensor having a photoconductive layer). Also, 8, ni, G
hosh, Tom Feng.
J、Appl、 Ph5y、、 49(12)、 59
B2(1978)に記載されているように太陽電池の光
導電層としても用いることができる。J, Appl, Ph5y, 49(12), 59
B2 (1978), it can also be used as a photoconductive layer in solar cells.
また、本発明のジスアゾ化合物は光電気泳動システムに
おける光導電性着色粒子及び乾式または湿式の電子写真
現像剤の着色粒子としても用いることができる。Further, the disazo compound of the present invention can be used as photoconductive colored particles in a photoelectrophoresis system and colored particles in a dry or wet electrophotographic developer.
また、本発明のジスアゾ化合物を、特公昭3717.1
62号、特開昭55−19,063号、8
特開昭55−161,250号、特開昭57−147,
656号公報に開示されているように、オキサジアゾー
ル誘導体、ヒドラジン誘導体等の前述の電荷担体輸送性
化合物と共にフェノール樹脂などのアルカリ可溶性樹脂
中に分散し、アルミニウムなどの導電性支持体上に塗布
、乾燥後、画像露光、トナー現像、アルカリ水溶液によ
るエツチングにより、高解像力、高耐久性、高感度の印
刷版が得られるほか、プリント回路を作成することがで
きる。Further, the disazo compound of the present invention can be used in Japanese Patent Publication No. 3717.1
62, JP 55-19,063, 8 JP 55-161,250, JP 57-147,
As disclosed in Japanese Patent No. 656, the above-mentioned charge carrier transporting compounds such as oxadiazole derivatives and hydrazine derivatives are dispersed in an alkali-soluble resin such as a phenol resin, and the mixture is coated on a conductive support such as aluminum. After drying, image exposure, toner development, and etching with an alkaline aqueous solution yield a printing plate with high resolution, high durability, and high sensitivity, and it is also possible to create printed circuits.
実施例1
化合物群No、 (1)でCp’が(Cp’ −21)
であるジスアゾ化合物5部とポリエステル樹脂(商品名
バイロン200、東洋紡■製)5部をテトラヒドロフラ
ン50部に添加し、ボールミルで12時間分散した後、
この分散波をワイヤーラウンドロッドを用いて導電性支
持体(75μmのポリエチレンテレフタレート支持体上
にアルミニウムの蒸着膜を有する。商品名メタルミー7
5TS、東し■製)上に塗布、乾燥して厚さ約0.5μ
mの電荷発生層を得た。Example 1 Compound group No. (1) has Cp'(Cp' -21)
After adding 5 parts of a disazo compound and 5 parts of a polyester resin (trade name: Vylon 200, manufactured by Toyobo ■) to 50 parts of tetrahydrofuran and dispersing in a ball mill for 12 hours,
This dispersion wave is transmitted using a wire round rod to a conductive support (a 75 μm polyethylene terephthalate support with an aluminum vapor-deposited film.Product name: Metal Me 7).
5TS, manufactured by Toshi ■) and dried to a thickness of approximately 0.5μ.
A charge generation layer of m was obtained.
次にこの電荷発生層上にp ノ)ベンズアルデヒド−N。Next, p B) Benzaldehyde-N.
エニルヒドラゾン
(ジフェニルアミ
メチル−N′ −)
3.6部、ポリカーボネート樹脂(パンライトに130
0、蛮人■製)4部、ジクロロメタン13.3部と1,
2−ジクロロエタン26.6部を混合溶解した溶液をア
プリケーターを用いて塗布し、厚さ17μmの電荷輸送
層を形成させて2層からなる感光層を有する電子写真感
光体を作成した。Enylhydrazone (diphenylamimethyl-N'-) 3.6 parts, polycarbonate resin (130 parts for Panlite)
0, made by Barbarian ■) 4 parts, dichloromethane 13.3 parts and 1,
A solution prepared by mixing and dissolving 26.6 parts of 2-dichloroethane was applied using an applicator to form a charge transport layer having a thickness of 17 μm, thereby producing an electrophotographic photoreceptor having a two-layer photosensitive layer.
これらの感光体を静電複写紙試験装置(@川口電機製作
新製、5P−428型)を用いて次のようにして電子写
真特性を評価した(スタチック方式で測定)。まず感光
体を一6KVのコロナ放電により帯電せしめた時の初期
表面電位V、、30秒間暗所に放置した時の表面電位V
。を測定した。The electrophotographic properties of these photoreceptors were evaluated using an electrostatic copying paper tester (@Kawaguchi Denki Seisaku Shin, Model 5P-428) as follows (measured using a static method). First, the initial surface potential V when the photoreceptor is charged with a corona discharge of 16 KV, and the surface potential V when it is left in a dark place for 30 seconds.
. was measured.
次いでタングステンランプの光を感光体表面における照
度を31uxになるようにして露光し、表面電位が初期
表面電位■。の半分に減衰するのに要する露光量E50
及び露光30秒後の表面電位(残留電位VR)をそれぞ
れ測定した。また同様の測定を3000回繰り返して行
った。結果を第5表に示す。Next, the photoreceptor surface was exposed to light from a tungsten lamp at an illuminance of 31 ux, and the surface potential was the initial surface potential ■. The exposure amount E50 required to attenuate by half of
And the surface potential (residual potential VR) after 30 seconds of exposure was measured. Further, similar measurements were repeated 3000 times. The results are shown in Table 5.
実施例2〜15
実施例1において化合物群No、(1)でCp’ が(
Cp’ −21)であるジスアゾ化合物5部の代わり
に第6表に示すジスアゾ化合物を用いた他は実施例1と
同様にして2層構成の電子写真感光体を作成し実施例1
と同様にE50、■8、Vo、VRを測定した。結果を
第6表に示す。Examples 2 to 15 In Example 1, compound group No. (1) has Cp' (
Example 1 An electrophotographic photoreceptor having a two-layer structure was prepared in the same manner as in Example 1 except that the disazo compound shown in Table 6 was used instead of 5 parts of the disazo compound which is Cp'-21).
E50, ■8, Vo, and VR were measured in the same manner as above. The results are shown in Table 6.
実施例16
化合物群No(1)でCp’が(Cp’ −21)であ
るジスアゾ化合物5部と実施例1で用いたヒドラゾン化
合物40部とベンジルメタアクリレ−1・とメタアクリ
ル酸のコポリマー(〔η〕 30°Cメチルエチルケト
ン−0,12、メタアクリル酸含有ft32. 9%)
100部とをジクロロメタン660部に添加し、ボー
ルミルで12時間分散した。Example 16 5 parts of a disazo compound whose Cp' is (Cp' -21) in compound group No. (1), 40 parts of the hydrazone compound used in Example 1, a copolymer of benzyl methacrylate-1 and methacrylic acid ([η] 30°C methyl ethyl ketone-0.12, methacrylic acid content ft32.9%)
100 parts of the mixture were added to 660 parts of dichloromethane and dispersed in a ball mill for 12 hours.
この分散液を砂目立てした厚さ0.25mmのアルミ板
上に塗布、乾燥し膜厚6μmの電子写真感光層を有する
電子写真印刷版材料を作製した。This dispersion was coated on a grained aluminum plate with a thickness of 0.25 mm and dried to produce an electrophotographic printing plate material having an electrophotographic photosensitive layer with a thickness of 6 μm.
この試料を暗所でコロナ放電(+6KV)することによ
り、感光層の表面電位を+500Vに帯電させた後、色
温度2854にのタングステン光を試料面での照度2.
0ルツクスで露光したところ、半減露光量(E50)は
2. 2 ] ux−secであった。After charging the surface potential of the photosensitive layer to +500V by corona discharge (+6KV) on this sample in a dark place, tungsten light with a color temperature of 2854 was applied to the sample surface at an illuminance of 2.
When exposed at 0 lux, the half-life exposure (E50) was 2. 2 ] ux-sec.
つぎに、この試料を暗所で表面電位を+500Vに帯電
′させた後、ポジ画像の透明原稿と密着させて画像露光
した。これをl5operH(エッソスタンダート社製
、石油系溶剤)Iff、微粒子状に分散されたポリメチ
ルメタアクリレ−1−(+−ナー)5g及び大豆油レシ
チン0.01gからなる液体現像剤中に浸漬し、鮮明な
ポジのトナー画像を得ることができた。Next, this sample was charged to a surface potential of +500 V in a dark place, and then imagewise exposed by bringing it into close contact with a transparent original with a positive image. This was immersed in a liquid developer consisting of l5operH (manufactured by Esso Standard, petroleum solvent) Iff, 5 g of polymethyl methacrylate-1-(+-ner) dispersed in fine particles, and 0.01 g of soybean oil lecithin. However, a clear positive toner image could be obtained.
更に100℃で30秒間加熱してトナー画像を定着した
。この印刷版桐材をメタ珪酸すトリウム水和物70gを
クリセリン140部、エチレングリコール550部、お
よびエタノール150部に溶解したエツチング液に1分
間浸漬し、水流で軽くブラッシングしながら洗うことに
より、トナーの付着していない部分の感光層を除去し印
刷版を得た。The toner image was further fixed by heating at 100° C. for 30 seconds. This printing plate paulownia material was immersed for 1 minute in an etching solution in which 70 g of thorium metasilicate hydrate was dissolved in 140 parts of chrycerin, 550 parts of ethylene glycol, and 150 parts of ethanol, and washed with a stream of water while lightly brushing. A printing plate was obtained by removing the photosensitive layer in the areas to which it was not attached.
このようにして作製した印刷版をハフダスター600C
Dオフセツト印刷機を用いて印刷したところ、地片れの
ない非常に鮮明な印刷物を5万枚印刷することができた
。The printing plate produced in this way was
When printing was performed using a D-offset printing machine, 50,000 sheets of very clear prints with no peeling could be printed.
Claims (1)
を含有した層を設けて成るか、または電荷輸送化合物含
有層及び電荷発生化合物含有層を設けて成る電子写真感
光体において、電荷発生化合物として下記一般式〔1〕
で表わされるジスアゾ化合物を含有することを特徴とす
る電子写真感光体。 ▲数式、化学式、表等があります▼〔1〕 一般式〔1〕において、Ar^1、Ar^2及びAr^
3はアリーレン基、2価の縮合多環式芳香族基または2
価の複素芳香環基を表す。Cpはカプラー残基を表す。 R^5及びR^6は水素原子、アルキル基、アルコキシ
基、シアノ基、ニトロ基またはハロゲン原子を表す。[Scope of Claims] An electrophotographic photoreceptor comprising a layer containing a charge transporting compound and a charge generating compound, or a layer containing a charge transporting compound and a layer containing a charge generating compound on a conductive support. In the following general formula [1] as a charge generating compound:
An electrophotographic photoreceptor comprising a disazo compound represented by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [1] In general formula [1], Ar^1, Ar^2, and Ar^
3 is an arylene group, a divalent fused polycyclic aromatic group, or 2
represents a valent heteroaromatic ring group. Cp represents a coupler residue. R^5 and R^6 represent a hydrogen atom, an alkyl group, an alkoxy group, a cyano group, a nitro group, or a halogen atom.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP17744589A JPH0342669A (en) | 1989-07-10 | 1989-07-10 | Electrophotographic sensitive body |
US07/549,030 US5106712A (en) | 1989-07-07 | 1990-07-06 | Electrophotographic photoreceptor containing bisazo compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP17744589A JPH0342669A (en) | 1989-07-10 | 1989-07-10 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0342669A true JPH0342669A (en) | 1991-02-22 |
Family
ID=16031075
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP17744589A Pending JPH0342669A (en) | 1989-07-07 | 1989-07-10 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0342669A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7247057B2 (en) | 2003-03-27 | 2007-07-24 | Hirose Electric Co., Ltd. | Connector assembly of connector and transmission board |
-
1989
- 1989-07-10 JP JP17744589A patent/JPH0342669A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7247057B2 (en) | 2003-03-27 | 2007-07-24 | Hirose Electric Co., Ltd. | Connector assembly of connector and transmission board |
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