JPS63282745A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS63282745A JPS63282745A JP11677087A JP11677087A JPS63282745A JP S63282745 A JPS63282745 A JP S63282745A JP 11677087 A JP11677087 A JP 11677087A JP 11677087 A JP11677087 A JP 11677087A JP S63282745 A JPS63282745 A JP S63282745A
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- azo pigment
- formula
- bonded
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000049 pigment Substances 0.000 claims abstract description 48
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
- 125000004970 halomethyl group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract 4
- 108091008695 photoreceptors Proteins 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000005647 linker group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 230000035945 sensitivity Effects 0.000 abstract description 12
- 239000000758 substrate Substances 0.000 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000003595 spectral effect Effects 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- -1 benzothiazoyl Chemical group 0.000 description 33
- 230000032258 transport Effects 0.000 description 32
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 18
- 238000000576 coating method Methods 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 7
- 239000005018 casein Substances 0.000 description 7
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 7
- 235000021240 caseins Nutrition 0.000 description 7
- 239000002800 charge carrier Substances 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229920002382 photo conductive polymer Polymers 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 229920001230 polyarylate Polymers 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-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
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical group C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 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 compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium 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
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- 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 1
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 description 1
- JJTQXUIZDMWYKQ-UHFFFAOYSA-N 2-(1,2,2-triphenylethenyl)aniline Chemical compound C1(=CC=CC=C1)C(=C(C1=C(C=CC=C1)N)C1=CC=CC=C1)C1=CC=CC=C1 JJTQXUIZDMWYKQ-UHFFFAOYSA-N 0.000 description 1
- IWUACMRENZNWBB-UHFFFAOYSA-N 2-(2-chlorophenyl)-1,3-oxazole Chemical compound ClC1=CC=CC=C1C1=NC=CO1 IWUACMRENZNWBB-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-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
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0687—Trisazo dyes
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
[#!1.業上の東上分野]
本発明は電子写真感光体に関し、詳しくは特定の7ゾ顔
ネ4を含有する感光層を有する電子写真感光体に関する
。[Detailed description of the invention] [#! 1. TECHNICAL FIELD The present invention relates to an electrophotographic photoreceptor, and more particularly, to an electrophotographic photoreceptor having a photosensitive layer containing a specific 7-zoomone-4.
[従来の技術]
これまでセレン、硫化カドミウム、酸化亜鉛などの無機
光導電体を感光成分として利用した電子写真感光体は公
知である。[Prior Art] Electrophotographic photoreceptors using inorganic photoconductors such as selenium, cadmium sulfide, and zinc oxide as photosensitive components have been known.
一方、特定の有機化合物が光導電性を示すこと・が発見
されてから、数多くの有機光導電体が開発されてきた0
例えばポリ−N−ビニルカル/へツール、ポリビニルア
ントラセンなどの有機光導電性ポリマー、カルバゾール
、アントラセン、ピラゾリン類、オキサジアゾール類、
とドラシン類、アリールアルカン類などの低分子の有機
光導電体やフタロシアニン顔料、アゾ顔料、シアニン顔
料、多環キノン顔料、ペリレン系顔料、インジゴ染料、
・チオインジゴ染料あるいはスクエアリック酸メチン染
料などの有機顔料や染料が知られている。On the other hand, since the discovery that certain organic compounds exhibit photoconductivity, many organic photoconductors have been developed.
For example, organic photoconductive polymers such as poly-N-vinyl cal/hetool, polyvinylanthracene, carbazole, anthracene, pyrazolines, oxadiazoles,
and low-molecular organic photoconductors such as dracins, arylalkanes, phthalocyanine pigments, azo pigments, cyanine pigments, polycyclic quinone pigments, perylene pigments, indigo dyes,
- Organic pigments and dyes such as thioindigo dyes and squaric acid methine dyes are known.
特に、光導電性を有する有機顔料や染料は、無機材料に
比べて合成が容易で、しかも適当な波長域に光導電性を
示す化合物を選択できるバリエーションが拡大されたこ
となどから、数多くの光導電性有機顔料や染料が提案さ
れている0例えば、米国特許第4123270号明細書
、同第4247614号明細書、同第4251613号
明細書、同第4251614号明細書、同第42568
21号明細書、同第4260672号明細書、同第42
68596号す1細書、同第4278747号明細書、
同第4293628号明細書などに開示されたように電
荷発生層と電荷輸送層に機能分離した感光層における電
荷発生物質として光導電性を示すアゾ顔料を用いた電子
写真感光体などが知られている。In particular, photoconductive organic pigments and dyes are easier to synthesize than inorganic materials, and the variety of compounds that exhibit photoconductivity in an appropriate wavelength range has expanded, making it possible to use a large number of photoconductive compounds. Conductive organic pigments and dyes have been proposed. For example, US Pat. No. 4,123,270, US Pat. No. 4,247,614, US Pat. No. 4,251,613, US Pat.
Specification No. 21, Specification No. 4260672, Specification No. 42
Specification No. 68596, Specification No. 4278747,
As disclosed in the specification of the same No. 4293628, an electrophotographic photoreceptor using an azo pigment exhibiting photoconductivity as a charge generation substance in a photosensitive layer functionally separated into a charge generation layer and a charge transport layer is known. There is.
このような有機光導電体を用いた電子写真感光体はバイ
ンダーを適当に選択することによって塗工で生産できる
ため、極めて生産性が高く、安価な感光体を提供でき、
しかも有機顔料の選択によって感光波長域を自在にコン
トロールできる利点を有している反面、この感光体は感
度と耐久性の点で無機系の感光体に劣るのが実状である
。An electrophotographic photoreceptor using such an organic photoconductor can be produced by coating by appropriately selecting a binder, so it is possible to provide an extremely highly productive and inexpensive photoreceptor.
Moreover, while this photoreceptor has the advantage of being able to freely control the sensitive wavelength range by selecting the organic pigment, it is actually inferior to inorganic photoreceptors in terms of sensitivity and durability.
[発明が解決しようとする問題点]
本発明の目的は、実用的な高感度と繰り返し使用におけ
る安定な電位特性を有する新規な電子写真感光体を提供
することにある。[Problems to be Solved by the Invention] An object of the present invention is to provide a novel electrophotographic photoreceptor that has practical high sensitivity and stable potential characteristics during repeated use.
[問題点を解決する手段、作用]
本発明は、導電性支持体上に
一般式
(式中、R1およびR2は水素原子、置換基を有しても
よいアルキル基、アラルキル基、アリール基、複素環基
、ニトロ基、シアノ基、ハロゲン原子、ハロメチル基ま
たは置換アミノ基を示し、同じであっても異なっていて
もよく、また、R1、R2は共同で置換基を有してもよ
い環を形成してもよい、)で示す有機残基が、結合基を
介して結合してもよい置換もしくは無置換の芳香族炭化
水素環または芳香族複素環と結合した構造を有するアソ
顔ネ゛1を含む感光層を有することを特徴とする′重子
写真感光体から構成される。[Means for Solving the Problems, Effects] The present invention provides a conductive support with a general formula (wherein R1 and R2 are hydrogen atoms, an alkyl group which may have a substituent, an aralkyl group, an aryl group, A heterocyclic group, a nitro group, a cyano group, a halogen atom, a halomethyl group, or a substituted amino group, which may be the same or different, and R1 and R2 may jointly have a substituent. An isophane group having a structure in which an organic residue represented by ) is bonded to a substituted or unsubstituted aromatic hydrocarbon ring or aromatic heterocycle which may be bonded via a bonding group. The photoreceptor is composed of a photoreceptor characterized in that it has a photosensitive layer containing 1.
上記一般式(I)で示される有機残基について旦体的に
説明すると、
R1およびR2の示す、アルキル基としてはメチル、エ
チル、プロピル、ブチルなどの基が挙げられ、アラルキ
ル基としてはベンジル、フェネチル、ナフチルエチルな
どの基が挙げられ、アリール2qとしてはフェニル、ナ
フチル、アントラニル、フェナンスリルなどの基が挙げ
られ、複素環基としてはピリジル、キノリル、ベンゾオ
キサゾールイル、ベンゾチアゾールイル、ベンズイミダ
ゾールイル、ベンゾトリアゾールイルなどの基が挙げら
れ、ハロゲン原子としてはフッ素原子、塩素原子、臭素
原子などが挙げられ、ハロメチル基としてはトリフルオ
ロメチル、クロロメチルなどの基が挙げられる。To explain the organic residue represented by the above general formula (I) in detail, examples of the alkyl group represented by R1 and R2 include methyl, ethyl, propyl, butyl, etc., and examples of the aralkyl group include benzyl, Examples of the aryl 2q include phenyl, naphthyl, anthranyl, phenanthryl, etc., and examples of the heterocyclic group include pyridyl, quinolyl, benzoxazolyl, benzothiazoyl, benzimidazoyl, Examples include groups such as benzotriazoleyl, halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, etc., and halomethyl groups include trifluoromethyl, chloromethyl, and the like.
上記表現の置換基とは、メチル、エチル、プロピルなど
のアルキル基、メトキシ、エトキシなどのアルコキシ基
、フッ素原子、塩素原子、臭素原子などのハロゲン原子
、ジメチルアミノ、ジエチルアミノなどのフルキルアミ
ノ基、フェニルカルバモイル基、ニトロ基、シアノ基、
トリフルオロメチルなどのハロメチル基などを意味する
。The substituents in the above expressions include alkyl groups such as methyl, ethyl, and propyl, alkoxy groups such as methoxy and ethoxy, halogen atoms such as fluorine, chlorine, and bromine, fulkylamino groups such as dimethylamino and diethylamino, and phenylcarbamoyl. group, nitro group, cyano group,
It means a halomethyl group such as trifluoromethyl.
さらにR1およびR2の示す、置換アミン基としてはジ
メチルアミノ、ジエチルアミノ、ジフェニルアミノ、ジ
ベンジルアミノおよびピロリル、ピロリジニル、ピペリ
ジノ、モルホリノなどの環状アミ7基が挙げられる。Furthermore, the substituted amine groups represented by R1 and R2 include dimethylamino, diethylamino, diphenylamino, dibenzylamino, and cyclic amine groups such as pyrrolyl, pyrrolidinyl, piperidino, and morpholino.
R,とR2が共同で形成する置換基を有してもよい環の
母核としては、例えば下記の母核が挙げ上記表現の置換
基とは、メチル、エチル、プロピルなどのアルキル基、
メトキシ、エトキシなどのアルコキシ基、フッ素原子、
塩素原子、臭素原子などのハロゲン原子、ニトロ基、シ
アノ基、トリフルオロメチルなどのハロメチル基を意味
する。Examples of the ring core which may have a substituent jointly formed by R and R2 include the following cores, and the substituents in the above expression include alkyl groups such as methyl, ethyl, and propyl;
Alkoxy groups such as methoxy and ethoxy, fluorine atoms,
It means a halogen atom such as a chlorine atom or a bromine atom, a nitro group, a cyano group, or a halomethyl group such as trifluoromethyl.
一般式(I)で示す有機残基が結合する、結合基を介し
て結合してもよい置換もしくは無置換の芳香族炭化水素
環、芳香族複素環としては、ベンゼン、ナフタレン、フ
ルオレン、フェナンスレン、アントラセン、ピレンなど
の炭化水素系芳香環、フラン、チオフェン、ピリジン、
インドール、ベンゾチアゾール、カルバゾール、アクリ
ドン、ジベンゾチオフェン、ベンゾオキサゾール、ベン
ゾトリアゾール、オキサジアゾール、チアジアゾールな
どの複素系芳香環、さらに上記芳香環を直接あるいは芳
香族性または非芳香族性基で結合したもの、例えばトリ
フェニルアミン、ジフェニルアミン、N−メチルジフェ
ニルアミン、ビフェニル、ターフェニル、ビナフチル、
フルオレノン、フェナンスレンキノン、アントラキノン
、ペンザントロン、ジフェニルオキサジアゾール、フェ
ニルベンゾオキサゾール、ジフェニルメタン、ジフェニ
ルスルホン、ジフェニルエーテル、ベンゾフェノン、ス
チルベン、ジスチリルベンゼン、テトラフェニル−p−
フ二二レンジアミン、テトラフェニルベンジジンなどが
挙げられる。Examples of substituted or unsubstituted aromatic hydrocarbon rings and aromatic heterocycles to which the organic residue represented by general formula (I) may be bonded via a bonding group include benzene, naphthalene, fluorene, phenanthrene, Hydrocarbon aromatic rings such as anthracene and pyrene, furan, thiophene, pyridine,
Heteroaromatic rings such as indole, benzothiazole, carbazole, acridone, dibenzothiophene, benzoxazole, benzotriazole, oxadiazole, thiadiazole, etc., and those in which the above aromatic rings are bonded directly or with an aromatic or non-aromatic group. , such as triphenylamine, diphenylamine, N-methyldiphenylamine, biphenyl, terphenyl, binaphthyl,
Fluorenone, phenanthrenequinone, anthraquinone, penzanthrone, diphenyloxadiazole, phenylbenzoxazole, diphenylmethane, diphenylsulfone, diphenyl ether, benzophenone, stilbene, distyrylbenzene, tetraphenyl-p-
Examples include fluorinated diamine and tetraphenylbenzidine.
上記環の有する置換基としては、メチル、エチル、プロ
ピル、ブチルなどのアルキル基、メトキシ、エトキシな
どのアルコキシ基、フッ素原子、塩素原子、臭素原子な
どのハロゲン原子、ジメチルアミノ、ジエチルアミノな
どのジアルキルアミノ基、ヒドロキシ基、ニトロ基、シ
アノ基、ハロメチル基あるいは一般式−N=N−Op
(m)で示される置換アゾ基が挙げられる。Examples of substituents on the above rings include alkyl groups such as methyl, ethyl, propyl, and butyl; alkoxy groups such as methoxy and ethoxy; halogen atoms such as fluorine, chlorine, and bromine; and dialkylamino such as dimethylamino and diethylamino. group, hydroxy group, nitro group, cyano group, halomethyl group or general formula -N=N-Op
Examples include substituted azo groups represented by (m).
Cpはフェノール性水酸基を有するカプラー残基を示し
、さらに詳細には以下の一般式で示す構造を有するもの
が挙げられる。Cp represents a coupler residue having a phenolic hydroxyl group, and more specifically includes those having a structure represented by the following general formula.
一般式 ’X p。general formula 'X p.
OHO)1
上記一般式中、Xはベンゼン環と縮合して、置換基を有
してもよいナフタレン環、アントラセン環、カルバゾー
ル環、ベンゾカルバゾール環、ジベンゾフラン環、ペン
シナ7トフラン環、フル号レノン環などの芳香族炭化水
素環または芳香族複素環を形成するのに必要な*機残基
を示す。OHO) 1 In the above general formula, X is fused with a benzene ring to form a naphthalene ring which may have a substituent, an anthracene ring, a carbazole ring, a benzocarbazole ring, a dibenzofuran ring, a pencinnatofuran ring, a fluorenone ring * Indicates a residue necessary to form an aromatic hydrocarbon ring or an aromatic heterocycle, such as.
R1およびR2は前記一般式(I)におけると同義、R
3およびR4は水素原子、置換基を有してもよいアルキ
ル基、アラルキル基、アリール基、複素環基あるいはR
3、R4の結合する窒素原子を環内に含む環状アミノ基
を示す。R1 and R2 have the same meaning as in the above general formula (I), R
3 and R4 are hydrogen atoms, alkyl groups that may have substituents, aralkyl groups, aryl groups, heterocyclic groups, or R
3. Indicates a cyclic amino group containing the nitrogen atom to which R4 is bonded in the ring.
R5およびR6は水素原子、置換基を有してもよいアル
キル基、アラルキル基、アリール基、複素環基を示す。R5 and R6 represent a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group, an aryl group, or a heterocyclic group.
R7は置換基を有してもよいアルキル基、アラルキル基
、アリール基あるいは複素環基を示す。R7 represents an alkyl group, an aralkyl group, an aryl group, or a heterocyclic group which may have a substituent.
Ylは置換基を有してもよい2価の炭化水素環基あるい
は複素環基を示す。Yl represents a divalent hydrocarbon ring group or a heterocyclic group which may have a substituent.
OH。Oh.
などが挙げられる。Examples include.
Y2は置換基を有してもよい2価の芳香族炭化水素環基
を示し、O−フェニレン、0−ナフチレン、ペリナフチ
レン、1,2−アンスリレン、9.10−フェナンスリ
レン基などが挙げられる。Y2 represents a divalent aromatic hydrocarbon ring group which may have a substituent, and examples thereof include O-phenylene, 0-naphthylene, perinaphthylene, 1,2-antrylene, and 9,10-phenanthrylene groups.
Y3は置換基を有してもよい2価の芳香族炭化水素環基
あるいは窒素原子を環内に冶む2価の複素環基を示し、
2価の芳香族炭化水素環基としてはO−7エニレン、O
−ナフチレン、ペリナフチレン、1.2−アンスリレン
、9.10−フェナンスリレン基などが挙げられ、窒素
原子を環内に含む2価の複素環基としては3.4−ピラ
ゾールジイル、2,3−ピリジンジイル、4.5−ピリ
ミジンジイル、6.7−インダゾールジイル、5.6−
ベンズイミダゾールジイル、6.7−キラリンジイル基
などが挙げられる。Y3 represents a divalent aromatic hydrocarbon ring group which may have a substituent or a divalent heterocyclic group containing a nitrogen atom in the ring,
As the divalent aromatic hydrocarbon ring group, O-7 enylene, O
-Naphthylene, perinaphthylene, 1,2-antrylene, 9,10-phenanthrylene groups, etc., and divalent heterocyclic groups containing a nitrogen atom in the ring include 3,4-pyrazolediyl, 2,3-pyridinediyl , 4.5-pyrimidinediyl, 6.7-indazolediyl, 5.6-
Examples include benzimidazolediyl and 6,7-chiralindiyl groups.
Bは酸素原子、硫黄原子、N−置換または無置換のイミ
ノ基を示し、Nの置換基としてはW1換基を有してもよ
いアルキル基、アラルキル基、アリール基が挙げられる
。B represents an oxygen atom, a sulfur atom, or an N-substituted or unsubstituted imino group, and examples of the substituent for N include an alkyl group, an aralkyl group, and an aryl group that may have a W1 substituent.
上記表現のアルキル基としてはメチル、エチルプロピル
、ブチルなどの基が挙げられ、アラルキル基トしてはベ
ンジル、フェネチル、ナフチルメチルなどの基が挙げら
れ、7リール基としてはフェニル、ジフェニル、ナフチ
ル、アンスリルなどの基が挙げられ、複素環基としては
ピリジル、チェニル、フリル、チアグリル、カルバゾリ
ル、ジベンゾフリル、ベンゾイミダゾリル、ベンゾチア
ゾリルなどの基が挙げられ、窒素原子を環内に含む環状
アミ7基としてはピロール、ピロリン、ピロリジン、ピ
ロリドン、インドール、インドリン、イソインドール、
カルバゾール、ベンゾインドール、イミダゾール、ピラ
ゾール、ピラゾリン、オキサジン、フェノキサジン、ベ
ンゾカルバゾールなどから誘導される環状アミノ基が挙
げられる。Examples of the alkyl group in the above expression include groups such as methyl, ethylpropyl, and butyl; examples of the aralkyl group include groups such as benzyl, phenethyl, and naphthylmethyl; and examples of the 7-aryl group include phenyl, diphenyl, naphthyl, Examples include groups such as anthryl, heterocyclic groups include pyridyl, chenyl, furyl, thiagrily, carbazolyl, dibenzofuryl, benzimidazolyl, and benzothiazolyl, and examples of cyclic amide groups containing a nitrogen atom in the ring include pyrrole. , pyrroline, pyrrolidine, pyrrolidone, indole, indoline, isoindole,
Examples include cyclic amino groups derived from carbazole, benzoindole, imidazole, pyrazole, pyrazoline, oxazine, phenoxazine, benzocarbazole, and the like.
また上記表現の置換基とはメチル、エチル、プロピルな
どのアルキル基、メトキシ、エトキシなどのフルコキシ
基、フッ素原子、塩素原子、臭素原子、ヨウ素原子など
のハロゲン原子、ジメチルアミノ、ジエチルアミノなど
のフルキルアミノ基、フェニルカルバモイル基、ニトロ
基、シアノ基、トリフルオロメチルなどのハロメチル基
などを意味する。The substituents in the above expressions are alkyl groups such as methyl, ethyl, and propyl; flukoxy groups such as methoxy and ethoxy; halogen atoms such as fluorine, chlorine, bromine, and iodine; and flukylamino groups such as dimethylamino and diethylamino. , phenylcarbamoyl group, nitro group, cyano group, halomethyl group such as trifluoromethyl, etc.
以下、本発明で用いるアゾ顔料の代表的な具体例を列挙
する。Typical specific examples of the azo pigment used in the present invention are listed below.
[七ノアゾ顔料]
八−A
[ジスアゾ顔料]
(l 1)
A−N−N−@−C)I−fll:H−@−0H−CH
−rffl 上H3
CユHs
(28) HD「一
方が一般式(m)で示す有機残基の場合」−例d上−
n
A−N−N−o−N(トN−N−B
H3
[トリスアゾ顔料]
六 A
本発明に用いられる下記一般式(x■)で示すカプラー
成分は、下記(X■)のアルコキシアセナフテンとブタ
ジェン誘導体をDials−Alder反応により環化
させて得られる(X■)の化合物を脱水素反応を行なっ
た後、三臭化ホウ素、塩化アルミニウムーエタンチオー
ル系などのルイス酸により脱アルキル化して合成できる
。[Sevenanoazo pigment] 8-A [Disazo pigment] (l 1) A-N-N-@-C) I-fll:H-@-0H-CH
-rffl Upper H3 CyuHs (28) HD "When one is an organic residue represented by general formula (m)" - Example d Upper - n A-N-N-o-N (tN-N-B H3 [Trisazo Pigment] 6 A The coupler component represented by the following general formula (x■) used in the present invention is obtained by cyclizing the alkoxyacenaphthene and butadiene derivative shown below (X■) by Dials-Alder reaction (X It can be synthesized by dehydrogenating the compound (2) and then dealkylating it with a Lewis acid such as boron tribromide or aluminum chloride-ethanethiol.
(xm)
上記合成方法により得られるカプラー成分は、置換基に
より異性体の混合物として得られるが、本発明において
は、いずれの異性体をも使用できる。(xm) The coupler component obtained by the above synthesis method can be obtained as a mixture of isomers depending on the substituents, but any isomer can be used in the present invention.
本発明に用いるアゾ顔料は、対応するアミン化合物を常
法によりジアゾ化し、アルカリ存在下で上記合成される
カプラー成分とカップリングさせるか、または、対応す
るアミノ化合物のジアゾニウム塩をホウフッ化塩または
塩化亜鉛複塩などの塩の形で一旦単離した後、適当な溶
剤、例えばN、N−ジメチルホルムアミド、ジメチルス
ルホキシドなどの有機溶剤中、酢酸ナトリウム、ピリジ
ン、トリエチルアミンなどの塩基の存在下でカップリン
グすることにより合成できる。The azo pigment used in the present invention can be prepared by diazotizing the corresponding amine compound by a conventional method and coupling it with the coupler component synthesized above in the presence of an alkali, or by converting the diazonium salt of the corresponding amino compound into a borofluoride salt or a chloride. Once isolated in the form of a salt such as a zinc double salt, it is coupled in a suitable solvent such as an organic solvent such as N,N-dimethylformamide or dimethyl sulfoxide in the presence of a base such as sodium acetate, pyridine or triethylamine. It can be synthesized by
また、本発明に用いるアゾ顔料のうち、ジスアゾ、トリ
スアゾ、テトラキスアゾ顔料の場合は、同一分子内に一
般式(x■)で示すカプラー成分が1個以上含まれてい
れば、他のカプラー成分を含んでいてもよい。Among the azo pigments used in the present invention, in the case of disazo, trisazo, and tetrakisazo pigments, if one or more coupler components represented by the general formula (x■) are contained in the same molecule, other coupler components May contain.
この場合の合成法としては、一般式(X X)で示すア
ミノ化合物をジアゾ化し、
(CHsCON)I)yvL−Ar −(NHJiL(
X X )(式中、Arは一般式(■)におけると同義
、文、mは1.2.3の整数であり、又+mは、2.3
または4である)
一般式(XI)で示すカプラー成分とカップリングさせ
た後、塩酸などの鉱酸類により加水分解しを得、再度ジ
アゾ化し、別のフェノール性水酸基を有するカプラー成
分とカップリングして合成してもよく、あるいは一般式
(XX[)で示すアミノ化合物 Ar−+MHz)y+
、 (X XI ) (式中、Arは一般式(n)に
おけると同義、nは2.3または4の整数である)を常
法によりジアゾニウム塩とし、これを一般式(XIX)
で示すカプラー成分と、これとは別のカプラー成分を混
合溶解した溶液中でカップリングして合成することもで
きる。In this case, the synthesis method is to diazotize the amino compound represented by the general formula (X
X
or 4) After coupling with the coupler component represented by general formula (XI), hydrolysis with mineral acids such as hydrochloric acid, diazotization again, and coupling with another coupler component having a phenolic hydroxyl group. Alternatively, an amino compound represented by the general formula (XX[) Ar-+MHz)y+
, (X
It can also be synthesized by coupling the coupler component represented by and another coupler component in a mixed solution.
次に本発明に用いるアゾ顔料の代表的な合成例を説明す
る。Next, a typical synthesis example of the azo pigment used in the present invention will be explained.
例示顔料(26)の合成
300 m lビーカーに水100m文、Sti!酸2
5mM (0,27モル)を入れ、氷水浴で冷却しなか
らN−エチル−3,6−ジアミツカルバゾール9.2g
(0,041モル)を加え、攪拌しつつ液温を3℃とし
た。Synthesis of Exemplary Pigment (26) 100 ml of water in a 300 ml beaker, Sti! acid 2
Add 5mM (0.27 mol), cool in an ice water bath, and add 9.2 g of N-ethyl-3,6-diamicrubazole.
(0,041 mol) was added thereto, and the liquid temperature was brought to 3°C while stirring.
次に亜硝酸ソーダ6.0g(0,087モル)を水10
m見に溶かした液を液温度を5℃以下にコントロールし
ながら10分間で滴下し、滴下終了後動温度でさらに3
0分攪拌した。Next, add 6.0 g (0,087 mol) of sodium nitrite to 10 ml of water.
Add the dissolved liquid dropwise over 10 minutes while controlling the liquid temperature to below 5°C, and then add another 3 minutes at a dynamic temperature after dropping.
Stirred for 0 minutes.
反応液にカーボンを加え癌過した後にホウフッ化ソーダ
13.5g (0,123モル)を水20mjlに溶か
した液を滴下し、析出したホウフッ化塩を濾取し、水洗
後、真空乾燥した。After adding carbon to the reaction solution and filtering it, a solution of 13.5 g (0.123 mol) of sodium borofluoride dissolved in 20 mjl of water was added dropwise, and the precipitated borofluoride salt was collected by filtration, washed with water, and then vacuum-dried.
収量11.2g、収率64% 次に1文ビーカーにD M F 350 m父を入れ。Yield 11.2g, yield 64% Next, put D M F 350 m father into the beaker.
これに2−ヒドロキシ−9,8−ジメチルフルオランセ
ン1f、8g(0,048モル)を溶解し、液温を5℃
に冷却し、先に得たホウフッ化1!!IO,Og (0
,023モル)を溶解させた後、トリエチルアミン5.
8g(0,058モル)を10分間で滴下し、その後2
時間纜 した。8 g (0,048 mol) of 2-hydroxy-9,8-dimethylfluoranthene 1f was dissolved in this, and the liquid temperature was adjusted to 5°C.
Cool the borofluoride obtained earlier! ! IO, Og (0
, 023 mol), then triethylamine 5.
8 g (0,058 mol) was added dropwise over 10 minutes, then 2
The time was right.
反応液を 過した後、N、N−ジメチルホルムアミド3
00m文で5回洗浄し、アセトンで置換し、真空乾燥に
より、[1的のアゾ顔料である例示顔料(26)を得た
。収量13.4g 収率78.3%(ホウフッ化塩ベ
ース)
元素分析
計算値(%) 実測値(%)
C80,5180,40
H5,815,88
N 9.39 9.36
前述のアゾ顔料を有する被膜は光導電性を示しド述する
電子写真感光体の感光層に用いることができる。After filtering the reaction solution, N,N-dimethylformamide 3
The mixture was washed 5 times with 00m water, replaced with acetone, and dried under vacuum to obtain Exemplary Pigment (26), which is an azo pigment of [1]. Yield 13.4g Yield 78.3% (borofluoride salt base) Elemental analysis calculated value (%) Actual value (%) C80,5180,40 H5,815,88 N 9.39 9.36 The above azo pigment A coating having the above-mentioned composition exhibits photoconductivity and can be used as a photosensitive layer of an electrophotographic photoreceptor as described above.
本発明の好ましい具体例では、゛重子写真感光体の感光
層を゛電荷発生層と電荷輸送層に機能分離した電f写真
感光体における電荷発生物質に、前述のアゾ顔ネ1を適
用することができる。In a preferred embodiment of the present invention, the above-mentioned Azoface 1 is applied to a charge generating substance in an electrophotographic photoreceptor in which the photosensitive layer of the photoreceptor is functionally separated into a charge generation layer and a charge transport layer. Can be done.
電荷発生層は、十分な吸光度を得るために、できる限り
多くの電荷発生物質を含有し、かつ発生した゛重荷キャ
リアの飛程を短くするために薄膜層、例えば5終以下、
好ましくは0.01−1gの膜厚をもつ薄112層とす
ることが好ましい。The charge generation layer contains as much charge generation substance as possible in order to obtain sufficient absorbance, and is a thin film layer, for example, 5 or less, in order to shorten the range of the generated heavy carriers.
Preferably, it is a thin 112 layer with a thickness of 0.01-1 g.
このことは入射光稙の大部分が電荷発生層で吸収されて
多く電荷キャリアを生成すること、さらに発生したキャ
リアを再結合や捕獲(トラップ)により失活することな
く電荷輸送層に注入する必要があることに起因している
。This means that most of the incident light is absorbed by the charge generation layer and generates a large number of charge carriers, and that the generated carriers must be injected into the charge transport layer without being deactivated by recombination or trapping. This is due to the fact that
電荷発生層は、前記アゾ顔料を適当なバインダーに分散
させ、これを基体の上に塗工することによって形成でき
る。?l!荷発生層を塗工によって形成する際に用い得
るバインダーとしては広範な絶縁性樹脂から選択でき、
またポリ−N−ビニルカルバゾール、ポリビニルアント
ラセンやポリビニルピレンなどの有機光導電性ポリマー
から選択できる。The charge generation layer can be formed by dispersing the azo pigment in a suitable binder and coating it on the substrate. ? l! The binder that can be used when forming the load generation layer by coating can be selected from a wide range of insulating resins.
It can also be selected from organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene and polyvinylpyrene.
&’r t L、 <はポリビニルブチラール、ボリア
リレート(ビスフェノールAとフタル酸の縮重合体など
)、ポリカーボネート、ポリエステル、フェノキシ樹脂
、ポリ酢酸ビニル、アクリル樹脂、ポリアクリルアミド
、ポリアミド、ポリビニルピリジン、セルロース系樹脂
、ポリウレタン、エポキシ樹脂、カゼイン、ポリビニル
アルコール、ポリビニルピロリドンなどの絶縁性樹脂を
挙げることができる。&'r t L, < is polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.), polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide, polyamide, polyvinylpyridine, cellulose type Examples include insulating resins such as resin, polyurethane, epoxy resin, casein, polyvinyl alcohol, and polyvinylpyrrolidone.
電荷発生層中に含有する樹脂は、80重量%以下、好ま
しくは40重量%以下が適している。The resin contained in the charge generation layer is suitably 80% by weight or less, preferably 40% by weight or less.
これらの樹脂を溶解する溶剤は、樹脂の種類によって異
なり、また後述の電荷輸送層や下引層を溶解しないもの
から選択することが好ましい。The solvent that dissolves these resins varies depending on the type of resin, and is preferably selected from those that do not dissolve the charge transport layer and undercoat layer described below.
具体的な有機溶剤としては、メタノール、エタノール、
インプロパツールなどのアルコール類、アセトン、メチ
ルエチルケトン、シクロヘキサノンなどのケトン類、N
、N−ジメチルホルムアミド、N、N−ジメチルアセト
アミドなどのアミド類、ジメチルスルホキシドなどのス
ルホキシド類、テトラヒドロフラン、ジオキサン、エチ
レングリコールモノメチルエーテルなどのエーテル類、
酢酸メチル、酢酸エチルなどのエステル類、クロロホル
ム、塩化メチレン、ジクロルエチレン、四j!1化炭素
、トリクロルエチレンなどの脂肪族ハロゲン化炭化水素
類あるいはベンゼン、トルエン、キシレン、リグロイン
、モノクロルベンゼン、ジクロルベンゼンなどの芳香族
炭化水素類などを用いることができる。Specific organic solvents include methanol, ethanol,
Alcohols such as Impropatool, ketones such as acetone, methyl ethyl ketone, cyclohexanone, N
, amides such as N-dimethylformamide and N,N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide, ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether;
Esters such as methyl acetate and ethyl acetate, chloroform, methylene chloride, dichloroethylene, 4j! Aliphatic halogenated hydrocarbons such as carbon monocide and trichloroethylene, or aromatic hydrocarbons such as benzene, toluene, xylene, ligroin, monochlorobenzene and dichlorobenzene, etc. can be used.
塗工は、浸漬コーティング法、スプレーコーティング法
スピンナーコーティング法、ビードコーティング法、マ
イヤーバーコーティング法、ブレードコーティング法、
ローラーコーティング法、カーテンコールコーティング
法などのコーティング法を用いて行なうことができる。Coating methods include dip coating, spray coating, spinner coating, bead coating, Meyer bar coating, blade coating,
This can be carried out using a coating method such as a roller coating method or a curtain call coating method.
乾顛は、室温における指触乾燥後、加熱乾燥する方法が
好ましい、加熱乾燥は、30〜200°Cの温度で5分
〜2時間の範囲の時間で、静止または送風下で行なうこ
とができる。For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying can be carried out at a temperature of 30 to 200°C for a time in the range of 5 minutes to 2 hours, either stationary or under ventilation. .
電荷輸送層は、前述の電荷発生層と電気的に接続されて
おり、電界の存在下で電荷発生層から注入された電荷キ
ャリアを受は取るとともに、これらの電荷キャリアを表
面まで輸送できる機能を有している。この際、この電荷
輸送層は電荷発生層の上に積層されていてもよく、また
その下に積層されていてもよい、しかし、電荷輸送層は
電荷発生層の上に積層されていることが好ましい。The charge transport layer is electrically connected to the charge generation layer described above, and has the function of receiving and taking charge carriers injected from the charge generation layer in the presence of an electric field, and transporting these charge carriers to the surface. have. In this case, this charge transport layer may be laminated on top of the charge generation layer, or may be laminated below it. However, it is not recommended that the charge transport layer be laminated on the charge generation layer. preferable.
光導電体は、一般に?It荷キャリアを輸送する機能を
有しているので、電荷輸送層はこの光導電体によって形
成できる。What are photoconductors in general? Since it has the function of transporting It charge carriers, a charge transport layer can be formed by this photoconductor.
電荷輸送層における電荷キャリアを輸送する物質(以下
、電荷輸送物質という)は、前述の電荷発生層が感応す
る電磁波の波長域に実質的に非感応性であることが好ま
しい、ここでいうi!電磁波は、γ線、X線、紫外線、
可視光線、近赤外線、赤外線、遠赤外線などを包含する
広義の光線の定義を包含する。The substance that transports charge carriers in the charge transport layer (hereinafter referred to as charge transport material) is preferably substantially insensitive to the wavelength range of electromagnetic waves to which the charge generation layer is sensitive, i! Electromagnetic waves include gamma rays, X-rays, ultraviolet rays,
Includes a broad definition of light that includes visible light, near-infrared light, infrared light, far-infrared light, etc.
電荷輸送層の光感応性波長域が電荷発生層のそれと一致
またはオーバーラツプする時には、両者テ発生した電荷
キャリアが相配に捕獲し合い、結果的には感度の低ドの
原因となる。When the photosensitive wavelength range of the charge transport layer coincides with or overlaps that of the charge generation layer, the charge carriers generated by both layers mutually capture each other, resulting in a low sensitivity.
電荷輸送物質としては’ltE子輸送性物質と正札輸送
性物質があり、電子輸送性物質としてはクロルアニル、
ブロモアニル、テトラシアノエチレン、テトラシアノキ
ノジメタン、2,4.7−ドリニトロー9−フルオレノ
ン、2,4,5.7−チトラニトロキサントン、2,4
.8−トリニドロチオキサントンなどの電子吸引性物質
やこれら電子吸引性物質を高分子化したものなどがある
。Charge transporting substances include 'ltE electron transporting substances and regular transporting substances, and electron transporting substances include chloranyl,
Bromoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-dolinitro-9-fluorenone, 2,4,5,7-titranitroxanthone, 2,4
.. Examples include electron-withdrawing substances such as 8-trinidrothioxanthone, and polymerization of these electron-withdrawing substances.
正孔輸送性物質としてはピレン、N−エチルカルバソー
ル、N−イソプロピルカルバゾール、N−メチルーN−
フェニルヒドラジノ−3−メチリデン−9−エチルカル
バゾール、N1.、N−ジフェニルヒドラジ/−3−メ
チリデン−9−エチルカルバソール、N、N−ジフェニ
ルヒドラジノ−3−メチリデン−10−二チルフェノチ
アジン。Examples of hole-transporting substances include pyrene, N-ethylcarbazole, N-isopropylcarbazole, N-methyl-N-
Phenylhydrazino-3-methylidene-9-ethylcarbazole, N1. , N-diphenylhydrazino-3-methylidene-9-ethylcarbasol, N,N-diphenylhydrazino-3-methylidene-10-ditylphenothiazine.
N、N−ジフェニルヒドラジノ−3−メチリデン−10
−エナルフェノキサジン、p−ジエチルアミ/ベンズア
ルデヒド−N、N−ジフェニルヒドラジノ、p−ビロリ
ジノペンズアルデヒトーN。N,N-diphenylhydrazino-3-methylidene-10
-enalphenoxazine, p-diethylamide/benzaldehyde-N, N-diphenylhydrazino, p-virolidinopenzaldehyde-N.
N−ジフェニルヒドラゾン、P−ジエチルベンズアルデ
ヒド−3−メチルベンズチアノリノン−2−ヒドランン
などのヒドラゾン類、2.5−ヒス(P−ジエチルアミ
ノフェニル)−1,3,4−オキサジアゾール、l−フ
ェニル−3−(p−ジエチルアミノスチリル)−5−(
p−ジエチルアミノフェニル)ピラゾリン、1−[キノ
リル(2))−3−(p−ジエチルアミノスチリル)−
5−(p−ジエチルアミノフェニル)ピラゾリン、1−
[ピリジル(2)]−3−(p−ジエチルアミノスチリ
ル)−5−(p−ジエチルアミノフェニル)ピラゾリン
、1−[レピジル(2) ] −3−(p−ジエチルア
ミノスチリル)−5−(p−ジエチルアミノフェニル)
ピラゾリン、1−[ピリジル(2)] −3−(α−メ
チル−p−ジエチルアミノスチリル)−5−(p−ジエ
チルアミノフェニル)ピラゾリン、スビロビラソリンな
どのピラゾリン類、α−フェニル−4−N、N−ジフェ
ニルアミノスチルベン、N−エチル−3−(α−フェニ
ルスチリル)カルバゾール、4−N、N−ジベンジルア
ミノ−9−フルオレノンデンなどのスチリル系化合物、
2−(p−ジエチル7ミノスチリル)−6−ジニチルア
ミノベンズオキサゾール、2−(p−ジエチルアミノフ
ェニル)−4−(p−ジメチルアミノフェニル)−5−
(2−クロロフェニル)オキサゾールなどのオキサゾー
ル系化合物、2−(p−ジエチルアミノスチリル)−6
−ジニチルアミノベンゾチアゾールなどのチアゾール系
化合物、ビス(4−ジエチルアミノ−2−メチルフェニ
ル)−フェニルメタンなどのトリアリールメタン系化合
物、1.1ビス(4−N、N−ジエチルアミノ−2−メ
チルフェニル)へブタン、1,1,2.2−テトラキス
(4−N、N−ジメチルアミノ−2−メチルフェニル)
エタンなどのポリアリールアルカン類、トリフェニルア
ミン、ポリ−N−ビニルカルバゾール、ポリビニルピレ
ン、ポリビニルアントラセン、ポリビニルアクリジン、
ポリ−9−ビニルフェニルアントラセン、ピレン−ホル
ムアルデヒド樹脂、エチルカル八ゾールーホルムアルデ
ヒド樹脂などが挙げられる。Hydrazones such as N-diphenylhydrazone, P-diethylbenzaldehyde-3-methylbenzthianolinone-2-hydran, 2,5-his(P-diethylaminophenyl)-1,3,4-oxadiazole, l-phenyl -3-(p-diethylaminostyryl)-5-(
p-diethylaminophenyl)pyrazoline, 1-[quinolyl(2))-3-(p-diethylaminostyryl)-
5-(p-diethylaminophenyl)pyrazoline, 1-
[pyridyl (2)]-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[lepidyl (2)]-3-(p-diethylaminostyryl)-5-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, phenyl)
Pyrazolines such as pyrazoline, 1-[pyridyl(2)]-3-(α-methyl-p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, subirovirazoline, α-phenyl-4-N, N- styryl compounds such as diphenylaminostilbene, N-ethyl-3-(α-phenylstyryl)carbazole, 4-N,N-dibenzylamino-9-fluorenondene,
2-(p-diethyl7minostyryl)-6-dinithylaminobenzoxazole, 2-(p-diethylaminophenyl)-4-(p-dimethylaminophenyl)-5-
Oxazole compounds such as (2-chlorophenyl)oxazole, 2-(p-diethylaminostyryl)-6
-thiazole compounds such as dinithylaminobenzothiazole, triarylmethane compounds such as bis(4-diethylamino-2-methylphenyl)-phenylmethane, 1.1bis(4-N,N-diethylamino-2-methyl phenyl)hebutane, 1,1,2,2-tetrakis(4-N,N-dimethylamino-2-methylphenyl)
Polyarylalkane such as ethane, triphenylamine, poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine,
Examples include poly-9-vinylphenylanthracene, pyrene-formaldehyde resin, and ethyl cartazoole-formaldehyde resin.
これらの44a電荷輸送物質の他にセレン、セレン−テ
ルル、アモルファスシリコン、硫化カドミウムなどの無
機材料も用いることができる。In addition to these 44a charge transport materials, inorganic materials such as selenium, selenium-tellurium, amorphous silicon, and cadmium sulfide can also be used.
また、これらの電荷輸送物質は1種または2種以上−組
合せて用いることができる。Further, these charge transport materials can be used alone or in combination of two or more.
電荷輸送物質が成膜性を有していないときには適当なバ
インダーを選択することによって被膜形成できる。バイ
ンダーとして使用できる樹脂は、例えばアクリル樹脂、
ボリアリレート、ポリエステル、ポリカーボネート、ポ
リスチレン、アクリロニトリル−スチレンコポリマー、
アクリロニトリル−ブタジェンコポリマー、ポリビニル
ブチラール、ポリビニルホルマール、ポリスルホン、ポ
リアクリルアミド、ポリアミド、塩素化ゴムなどの絶縁
性樹脂あるいはポリ−N−ビニルカルバゾールポリビニ
ルアントラセン、ボリビニルピレンなどの有機光導電性
ポリマーが挙げられる。When the charge transport material does not have film-forming properties, a film can be formed by selecting an appropriate binder. Examples of resins that can be used as binders include acrylic resin,
polyarylate, polyester, polycarbonate, polystyrene, acrylonitrile-styrene copolymer,
Examples include insulating resins such as acrylonitrile-butadiene copolymer, polyvinyl butyral, polyvinyl formal, polysulfone, polyacrylamide, polyamide, chlorinated rubber, and organic photoconductive polymers such as poly-N-vinylcarbazole polyvinylanthracene and polyvinylpyrene. .
電荷輸送層は、電荷キャリアを輸送できる限界があるの
で、必要以1−に膜厚を厚くすることができない、一般
的には5〜30.であるが、好ましい範囲は8〜20終
である。塗Iによって電荷輸送層を形成する際には、前
述したような適当なコーティング法を用いることができ
る。Since the charge transport layer has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary, generally from 5 to 30. However, the preferred range is 8-20. When forming the charge transport layer using Coating I, any suitable coating method as described above can be used.
このような電荷発生層と電荷輸送層の積層構造からなる
感光層は、導電層を有する基体の上に設けられる。導電
層を有する基体としては、基体自体が導電性をもつもの
、例えばアルミニウム、アルミニウム合金、銅、亜鉛、
ステンレス、バナジウム、モリブデン、クロム、チタン
、ニッケル、インジウム、金や白金などが用いられる。A photosensitive layer having such a laminated structure of a charge generation layer and a charge transport layer is provided on a substrate having a conductive layer. Examples of the substrate having a conductive layer include those whose substrate itself is conductive, such as aluminum, aluminum alloy, copper, zinc,
Stainless steel, vanadium, molybdenum, chromium, titanium, nickel, indium, gold, and platinum are used.
その他にアルミニウム、アルミニウム合金、酸化インジ
ウム、酸化錫、酸化インジウム−酸化錫合金などを真空
蒸着法によって被膜形成された層を有するプラスチック
(例えばポリエチレン、ポリプロピレン、ポリ塩化ビニ
ル、ポリエチレンテレフタレート、アクリル樹脂、ポリ
フッ化エチレンなど)、4電性粒子(例えばカーボンブ
ラック、銀粒子など)を適当な、<イングー樹脂に分散
した導電層をイ1するノ、(体、導′心性粒子をプラス
チックや紙に含浸した7、Ii体や導電性ポリマーを有
するプラスチックなどを用いることができる。In addition, plastics (e.g., polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, polyfluoride, (e.g., ethylene chloride), tetraelectric particles (e.g., carbon black, silver particles, etc.) are dispersed in a suitable <ingu resin>. 7. Plastics having an Ii body or a conductive polymer can be used.
導電層と感光層の中間に、バリヤーa俺と接着機能をも
つ下引層を設けることもできる。下引層はカゼイン、ポ
リビニルアルコール、ニトロセルロース、エチレン−ア
クリル酸コポリマー、ポリアミド(ナイロン6、ナイロ
ン66、ナイロン610、共重合ナイロン、アルコキシ
メチル化ナイロンなど)、ポリウレタン、ゼラチン、酸
化アルミニウムなどによって形成できる。下引層のl々
厚は0.1〜5μ、好ましくは0.5〜3弘が適当であ
る。A subbing layer having a barrier and adhesive function can also be provided between the conductive layer and the photosensitive layer. The subbing layer can be formed from casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer, polyamide (nylon 6, nylon 66, nylon 610, copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin, aluminum oxide, etc. . The appropriate thickness of the undercoat layer is 0.1 to 5 microns, preferably 0.5 to 3 microns.
導電層、電荷発生層、電荷輸送層の順に積層した感光体
を使用する場合において電荷輸送物質が電子輸送性物質
からなるときは、電荷輸送層表面を正に帯電する必要が
あり、帯電後露光すると露光部では電荷発生層において
生成した電子が電荷輸送層に注入され、その後1表面に
到達して正電旬を中和し、表面電位の減衰が生じ、未露
光部との間に静電コントラストが生じる。When using a photoreceptor in which a conductive layer, a charge generation layer, and a charge transport layer are laminated in this order, and the charge transport material is an electron transport material, the surface of the charge transport layer must be positively charged, and exposure after charging is required. Then, in the exposed area, the electrons generated in the charge generation layer are injected into the charge transport layer, and then reach the surface and neutralize the positive electrons, resulting in attenuation of the surface potential and an electrostatic charge between it and the unexposed area. Contrast occurs.
このようにしてできた静′宅潜像を負荷・l電性のトナ
ーで現像すれば、可視像が得られる。A visible image is obtained by developing the electrostatic latent image thus formed with a charged toner.
これを直接定着するか、あるいはトナー像を紙やプラス
チックフィルムなどに転写後、現像し定着することがで
きる。This can be directly fixed, or the toner image can be transferred to paper or plastic film and then developed and fixed.
また感光体−Eの静711潜像を転写紙の絶縁層上に転
写後視像し、定着する方法もとれる。現像剤の種類や現
像方法、定着方法は公知のものや公知の方法のいずれを
採用してもよく、特定のものに限定されるものではない
。Alternatively, a method may be used in which the static 711 latent image on the photoconductor-E is visually imaged after being transferred onto an insulating layer of a transfer paper and then fixed. The type of developer, the developing method, and the fixing method may be any known ones or methods, and are not limited to specific ones.
一方、電荷輸送物質が正孔輸送性物質からなる場合、電
荷輸送層表面を負に帯電する必要があり、帯′i!後、
露光すると露光部では電荷発生層において生成した正孔
が電荷輸送層に注入され、その後表面に達して負電荷を
中和し、表面電位の減衰が生じ未露光部との間に静電コ
ントラストが生じる。現像時には電子輸送性物質を用い
たときとは逆に正荷電性トナーを用いる必要がある。On the other hand, when the charge transport material is a hole transport material, the surface of the charge transport layer must be negatively charged, and the charge 'i! rear,
When exposed to light, holes generated in the charge generation layer are injected into the charge transport layer in the exposed area, and then reach the surface and neutralize the negative charge, causing a decrease in surface potential and creating an electrostatic contrast between it and the unexposed area. arise. During development, it is necessary to use a positively charged toner, contrary to when an electron transporting substance is used.
さらに本発明の別の具体例として、1ij述のアゾ顔ネ
1を電荷輸送物質とともに同一層に含有させた電7写真
感光体を挙げることができる。Further, as another specific example of the present invention, there may be mentioned an electrophotographic photoreceptor in which Azoface 1 described above is contained in the same layer together with a charge transporting substance.
この際、前述の°電荷輸送物質の他にポリ−N−ビニル
カルへソールとトリニトロフルオレノンからなる゛電荷
移動錯化合物を用いることができる。In this case, in addition to the above-mentioned charge transport materials, a charge transfer complex compound consisting of poly-N-vinylcalhesol and trinitrofluorenone can be used.
この例の電子写真感光体は、前記アゾ顔料と電荷移動錯
化合物をテトラヒドロフランに溶解されたポリエステル
溶液中に分散させた後、被膜形成させて作成できる。The electrophotographic photoreceptor of this example can be prepared by dispersing the azo pigment and the charge transfer complex compound in a polyester solution dissolved in tetrahydrofuran, and then forming a film thereon.
いずれの電子写真感光体においても用いる顔料は一般式
(1)で示される有機残基を有する特定のアゾ顔ネ4か
ら選ばれる少なくとも1種類の顔料を含有し、また必要
に応じて光吸収の異なる顔料を組合せて使用し感光体の
感度を高めたり、パンクロマチックな感光体を得るなど
の目的で一般式(1)で示される有機残基を有する特定
のアゾ顔料を2種類以上組合せたり、または公知の染料
、顔ネ4から選ばれた電荷発生物質と組合せて使用する
ことも可能である。The pigment used in any of the electrophotographic photoreceptors contains at least one type of pigment selected from specific azo pigments 4 having an organic residue represented by the general formula (1), and if necessary, has a light absorption property. For the purpose of increasing the sensitivity of a photoreceptor by using a combination of different pigments or obtaining a panchromatic photoreceptor, two or more types of specific azo pigments having an organic residue represented by the general formula (1) are combined, Alternatively, it can also be used in combination with a charge generating substance selected from known dyes and pigments.
本発明の電子写真感光体は電子写真複写機に利用するの
みならず、レーザープリンター、CRTプリンターなど
の電子写真応用分野にも広く用いることができる。The electrophotographic photoreceptor of the present invention can be used not only in electrophotographic copying machines, but also in a wide range of electrophotographic applications such as laser printers and CRT printers.
[実施例]
実施例1
アルミ板上にカゼインのアンモニア水溶液(カゼイン1
1.2g、28%アンモニア水1g、水222 m5L
)をマイヤーパーで乾燥後の膜厚が1.0JLとなるよ
うに塗布し乾燥した。[Example] Example 1 Ammonia aqueous solution of casein (casein 1
1.2g, 28% ammonia water 1g, water 222m5L
) was applied using Mayer Parr so that the film thickness after drying was 1.0 JL and dried.
次に、前記例示顔料(2)の5gをチトラヒドロフラン
95 冒又にブチラール樹脂(ブチラール化度63モル
%)2gを溶解した液に加え、サンドミルで2時間分散
した。この分散液を先に形成したカゼイン層の上に乾燥
後の膜厚が0.4%となるようにマイヤーパーで塗布し
乾燥して電荷発生層を形成した。Next, 5 g of the exemplary pigment (2) was added to a solution in which 2 g of butyral resin (butyralization degree: 63 mol %) was dissolved in 95% of titrahydrofuran, and dispersed in a sand mill for 2 hours. This dispersion was applied onto the previously formed casein layer using a Mayer Par so that the film thickness after drying was 0.4%, and dried to form a charge generation layer.
のヒドラゾン化合物5gとポリメチルメタクリレート(
数平均分子110万)5gをベンゼン70rslに溶解
し、これを電荷発生層の上に乾燥後の膜厚が19ルとな
るようにマイヤーパーで塗布し乾燥して電荷輸送層を形
成し、実施例1の電子写真感光体を作成した。5g of hydrazone compound and polymethyl methacrylate (
Dissolve 5 g of number average molecular weight (1.1 million) in 70 rsl of benzene, apply this onto the charge generation layer using a Mayer par so that the film thickness after drying is 19 ml, and dry to form a charge transport layer. An electrophotographic photoreceptor of Example 1 was prepared.
また前記例示顔N (2)に代えて他の例示顔料を用い
実施例2〜12に対応する電子写真感光体を作成した。Further, electrophotographic photoreceptors corresponding to Examples 2 to 12 were prepared using other exemplary pigments in place of the exemplary face N (2).
このようにして作成した電子写真感光体を静電複写紙試
験装置(Model 5P−428、川口電機■製)
を用い、スタチック方式で−5,5KVにコロナ帯電し
、暗所で1秒間保持した後、照度5ルツクスで露光し、
帯電特性を調べた。The electrophotographic photoreceptor thus prepared was tested using an electrostatic copying paper tester (Model 5P-428, manufactured by Kawaguchi Denki ■).
Using static method, corona charge to -5.5KV, hold for 1 second in a dark place, and then expose to light at an illuminance of 5 lux.
The charging characteristics were investigated.
帯電特性としては、表面電位(Vo )と1秒間暗減衰
させたときの電位を172に減衰するに必要な露光量(
El/2)を測定した。The charging characteristics include the surface potential (Vo) and the exposure amount (Vo) required to attenuate the potential to 172 when dark decayed for 1 second.
El/2) was measured.
結果を示す。Show the results.
1 (2) 710 4.12 (
26) 730 2.33
(6) 710 2.04
(10) 700 2.95
(13) 730 3.86
(14) 700 2.67
(18) 690 2.08
(20) 670 2.9
9 (27) 710 3.
511 (32) 690 2
.812 (33) 700
3.5比較例1〜3
実施例1で用いた7ゾ顔料に代えて、下記構造式の7ゾ
顔料を用いた他は実施例1と全く同等の方法により電子
写真感光体を作成し、同様に評価した。結果を示す。1 (2) 710 4.12 (
26) 730 2.33
(6) 710 2.04
(10) 700 2.95
(13) 730 3.86
(14) 700 2.67
(18) 690 2.08
(20) 670 2.9
9 (27) 710 3.
511 (32) 690 2
.. 812 (33) 700
3.5 Comparative Examples 1 to 3 Electrophotographic photoreceptors were prepared in the same manner as in Example 1, except that a 7zo pigment having the following structural formula was used in place of the 7zo pigment used in Example 1. They were evaluated in the same way. Show the results.
比較例1のアゾ顔料
比較例2のアゾ顔料
比較例3のアゾ顔料
1 600 8.2
2 550 10.8
3 610 7.5上記の結果か
らみて、本発明電子写真感光体は、比較例の電子写真感
光体に比し、いずれも充分な帯電詣と感度を宥している
ことが認められる。Azo pigment of Comparative Example 1 Azo pigment of Comparative Example 2 Azo pigment of Comparative Example 3 1 600 8.2 2 550 10.8 3 610 7.5 In view of the above results, the electrophotographic photoreceptor of the present invention has the following characteristics: It is recognized that all of them have sufficient chargeability and sensitivity compared to electrophotographic photoreceptors.
実施例13−18
実施例2で作成した電子写真感光体を、780nmの半
導体レーザーおよびそのスキャンニングユニットをタン
グステン光源に置き代えて静電複写紙試験装置(Mod
el 5F−428(7)改造機、川口電機■製)を
用い、スタチック方式で−5,5KVでコロナ帯電し、
暗所で1秒間保持した後、レーザー光で露光し、帯電特
性を調べた。Example 13-18 The electrophotographic photoreceptor prepared in Example 2 was used in an electrostatic copying paper tester (Mod) by replacing the 780 nm semiconductor laser and its scanning unit with a tungsten light source.
el 5F-428 (7) modified machine, manufactured by Kawaguchi Denki ■), statically charged with corona at -5.5 KV,
After being held in a dark place for 1 second, it was exposed to laser light and the charging characteristics were examined.
帯電特性としては、表面電位(Vo )と1秒間暗減衰
させたときの電位を1/2に減衰するに必要な露光量(
El/2)を測定した。The charging characteristics include the surface potential (Vo) and the amount of light exposure required to attenuate the potential by 1/2 when dark decaying for 1 second (Vo).
El/2) was measured.
また例示顔料を代えて実施例14〜18に対応する電子
写真感光体を作成し、同様に帯電特性を測定した。結果
を示す。Further, electrophotographic photoreceptors corresponding to Examples 14 to 18 were prepared by changing the exemplified pigments, and the charging characteristics were similarly measured. Show the results.
13 (26) 680 5.514 (
11,) 700 4.815 (15)
710 5.816 (16) 710
4.517 (34) 680 5.
918 (37) 690 4.9上記の結
果からみて、本発明の電子写真感光体はいずれもレーザ
ー光に対しても優れた感度を有することが認められる。13 (26) 680 5.514 (
11,) 700 4.815 (15)
710 5.816 (16) 710
4.517 (34) 680 5.
918 (37) 690 4.9 From the above results, it is recognized that all the electrophotographic photoreceptors of the present invention have excellent sensitivity to laser light.
実施例19〜21
実施例2,4.5で作成した電子写真感光体を用いて繰
り返し使用時の明部電位と暗部電位の変動を測定した。Examples 19 to 21 Using the electrophotographic photoreceptors prepared in Examples 2 and 4.5, fluctuations in bright area potential and dark area potential during repeated use were measured.
方法としては、−5,6KVのコロナ帯電器、露光光学
系、現像器、転写?F’を電器、除電露光光学系および
クリーナーを備えた電子写真複写機のシリンダーに感光
体を貼り付けた。The method includes a -5.6KV corona charger, an exposure optical system, a developer, and a transfer device. The photoreceptor was attached to the cylinder of an electrophotographic copying machine equipped with F', an electric device, a static elimination exposure optical system, and a cleaner.
この複写機を用いて、初期の明部電位(VL )と暗部
電位(VD )をそれぞれ−200V、−700vに設
定し、5.000回繰り返し使用した後のVLとvDを
測定した。結果を示す。Using this copying machine, the initial bright area potential (VL) and dark area potential (VD) were set to -200V and -700V, respectively, and VL and vD were measured after repeated use 5,000 times. Show the results.
比較例4〜6
比較例1〜3で作成した電子写真感光体を、実施例19
と同様の方法で縁り返し使用時の電位変動を測定した。Comparative Examples 4 to 6 The electrophotographic photoreceptors prepared in Comparative Examples 1 to 3 were
Potential fluctuations during use of edge-reversing were measured in the same manner as above.
結果を示す。Show the results.
上記の結果からにて、本発明の電子写真感光体は、繰り
返し使用時における電位変動の少ない優れた特性を有し
ていることが認められる。From the above results, it is recognized that the electrophotographic photoreceptor of the present invention has excellent characteristics with little potential fluctuation during repeated use.
実施例22
実施例2で作成した電荷発生層の上に、2,4.7−ド
リニトロー9−フルオレノン5gとポリ−4,4°−ジ
オキシジフェニル−2,2−プロパンカーボネート(分
子量30万)5gをテトラヒドロフラン70mJLに溶
解して調製した塗布液を乾燥後の塗工量が10g/m2
どなるように塗布し、乾燥した。Example 22 5 g of 2,4.7-dolinitro-9-fluorenone and poly-4,4°-dioxydiphenyl-2,2-propane carbonate (molecular weight: 300,000) were placed on the charge generation layer prepared in Example 2. The coating amount after drying the coating solution prepared by dissolving 5g in 70mJL of tetrahydrofuran is 10g/m2
I applied it and let it dry.
こうして作成した電子写真感光体を実施例1と同様の方
法で帯電特性の測定を行なった。但し、このときの帯電
極性を十とした。The charging characteristics of the electrophotographic photoreceptor thus prepared were measured in the same manner as in Example 1. However, the charging polarity at this time was set to 10.
vo :+700V
E 1 / 2 : 3 、941 u X 、 3
e C実施例23
アルミ蒸着ポリエチレンテレフタレートフィルムのアル
ミ面上に、膜厚0.5%のポリビニルアルコールの被膜
を形成した。vo:+700V E1/2:3,941uX,3
eC Example 23 A polyvinyl alcohol film having a film thickness of 0.5% was formed on the aluminum surface of an aluminum vapor-deposited polyethylene terephthalate film.
次に、実施例2で用いたジスアゾ顔料の分散液を先の形
成したポリビニルアルコール層の上に乾燥後の膜厚が0
.5牌となるようにマイヤーバーで塗布し、乾燥して電
荷発生層を形成した。Next, the dispersion of the disazo pigment used in Example 2 was applied onto the polyvinyl alcohol layer formed above so that the film thickness after drying was 0.
.. It was coated with a Mayer bar so as to form five tiles, and dried to form a charge generation layer.
のピラゾリン化合物5gとボリアリレート(ビスフェノ
ールAとテレフタル酸−インフタル酸の縮重合体)5g
をテトラヒト回フラン70rnlに溶かした液をi?!
荷発生層の上に乾燥後の膜厚が18μとなるように塗布
し、乾燥して電荷輸送層を形成した0作成した電子写真
感光体の帯電特性および耐久特性を実施例1および実施
例18と同様の方法によって測定した。結果を示す。5 g of pyrazoline compound and 5 g of polyarylate (condensation polymer of bisphenol A and terephthalic acid-inphthalic acid)
Dissolved in 70rnl of tetrahydrofuran, !
Example 1 and Example 18 The charging characteristics and durability characteristics of the electrophotographic photoreceptor prepared by coating the charge generation layer to a film thickness of 18 μm after drying and drying to form a charge transport layer were as follows. Measured using the same method. Show the results.
帯電特性 Vo ニー675
El/2 : 3.91ux、see
耐久特性
実施例24
厚さ100JLのアルミ板上にカゼインのアンモニア水
溶液を塗布し、乾燥して膜厚0.s#Lの下引層を形成
した。Charging characteristics Vo knee 675 El/2: 3.91ux, see Durability characteristics example 24 An ammonia aqueous solution of casein was applied onto a 100JL thick aluminum plate and dried to a film thickness of 0. A subbing layer of s#L was formed.
次に、2,4.7−)ジニトロ−9−フルオレノン5g
とポリ−N−ビニルカルバゾール(数平均分子930万
)5gをテトラヒドロフラン70m1に溶かして、電荷
移動錆化合物を形成した。Next, 5 g of 2,4.7-)dinitro-9-fluorenone
and 5 g of poly-N-vinylcarbazole (number average molecular weight: 9.3 million) were dissolved in 70 ml of tetrahydrofuran to form a charge transfer rust compound.
この電荷移動錯化合物と例示顔料(33)Igをポリエ
ステル(商品名バイロン、東洋紡@製)5gをテトラヒ
ドロフラン70mJLに溶かした液に加え、分散した。This charge transfer complex compound and exemplified pigment (33) Ig were added to a solution in which 5 g of polyester (trade name: Vylon, manufactured by Toyobo@) was dissolved in 70 mJL of tetrahydrofuran, and dispersed.
この分散液を下引層の上に乾燥後の膜厚が16μとなる
ように塗布し、乾燥した。This dispersion liquid was applied onto the undercoat layer so that the film thickness after drying was 16 μm, and dried.
こうして作成した電子写真感光体の帯電特性を実施例1
と同様の方法によって測定した。但し、帯電極性は十と
した。結果を示す。Example 1 Charging characteristics of the electrophotographic photoreceptor thus prepared
Measured using the same method. However, the charging polarity was set to 10. Show the results.
V6:+710
El/2:5.0文ux、sec
実施例25
アルミ板上にカゼインの下引層を設け、この上に実施例
2で用いた電荷輸送層、電荷発生層をこの順に積層した
層構成を異にする他は全〈実施例2と同様にして電子写
真感光体を作成し、帯電特性を測定した。但し帯電極性
は十とした。V6: +710 El/2: 5.0 sentences ux, sec Example 25 A casein subbing layer was provided on an aluminum plate, and the charge transport layer and charge generation layer used in Example 2 were laminated in this order on top of this. An electrophotographic photoreceptor was prepared in the same manner as in Example 2 except that the layer structure was different, and the charging characteristics were measured. However, the charging polarity was set to 10.
Vo :+685
El/2:4.0Rux、sec
[発明の効果]
本発明電子写真感光体は、特定のアゾ顔料を感光層に含
有させたことにより、当該アーゾ顔料を含む感光層内部
におけるキャリア発生効率ないしはキャリア輸送効率の
いずれか一方または双方が改善され、感度や耐久使用時
における電位安定性に優れ、また長波長城にまで感度を
有する顕著な効果を奏する。Vo: +685 El/2: 4.0Rux, sec [Effects of the Invention] The electrophotographic photoreceptor of the present invention contains a specific azo pigment in the photosensitive layer, thereby reducing carrier generation inside the photosensitive layer containing the azo pigment. Either or both of the efficiency and carrier transport efficiency are improved, the sensitivity and potential stability during long-term use are excellent, and the remarkable effect is that the sensitivity extends to long wavelengths.
Claims (5)
てもよいアルキル基、アラルキル基、アリール基、複素
環基、ニトロ基、シアノ基、ハロゲン原子、ハロメチル
基または置換アミノ基を示し、同じであっても異なって
いてもよく、また、R_1、R_2は共同で置換基を有
してもよい環を形成してもよい、)で示す有機残基が、
結合基を介して結合してもよい置換もしくは無置換の芳
香族炭化水素環または芳香族複素環と結合した構造を有
するアゾ顔料を含む感光層を有することを特徴とする電
子写真感光体。(1) General formula ▲ Numerical formula, chemical formula, table, etc. on the conductive support ▼ (I) (In the formula, R_1 and R_2 are hydrogen atoms, alkyl groups that may have substituents, aralkyl groups, aryl group, heterocyclic group, nitro group, cyano group, halogen atom, halomethyl group, or substituted amino group, which may be the same or different, and R_1 and R_2 may jointly have a substituent. The organic residues indicated by ), which may form a good ring, are
1. An electrophotographic photoreceptor comprising a photosensitive layer containing an azo pigment having a structure bonded to a substituted or unsubstituted aromatic hydrocarbon ring or aromatic heterocycle which may be bonded via a bonding group.
もしくは無置換の芳香族炭化水素環または芳香族複素環
を示し、R_1およびR_2は一般式( I )における
と同義であり、nは1、2、3または4の整数である、
)で示すアゾ顔料である特許請求の範囲第1項記載の電
子写真感光体。(2) The azo pigment has the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (II) (In the formula, Ar is a substituted or unsubstituted aromatic hydrocarbon ring that may be bonded via a bonding group or represents an aromatic heterocycle, R_1 and R_2 have the same meanings as in general formula (I), and n is an integer of 1, 2, 3 or 4;
) The electrophotographic photoreceptor according to claim 1, which is an azo pigment represented by:
選択される有機残基が少なくとも1個と前記選択された
有機残基とは異なる一般式 −N=N−Cp(III)(式中、Cpはフェノール性水
酸基を有するカプラー残基を示す、)で示す有機残基の
少なくとも1個とが同一分子内で結合基を介して結合し
てもよい置換もしくは無置換の芳香族炭化水素環または
芳香族複素環と結合した構造を有するアゾ顔料である特
許請求の範囲第1項記載の電子写真感光体。(3) The azo pigment has at least one organic residue selected from the organic residues represented by the general formula (I) and a general formula -N=N-Cp (III) different from the selected organic residues. (In the formula, Cp represents a coupler residue having a phenolic hydroxyl group.) A substituted or unsubstituted aromatic compound which may be bonded to at least one organic residue in the same molecule via a bonding group. The electrophotographic photoreceptor according to claim 1, which is an azo pigment having a structure bonded to a hydrocarbon ring or an aromatic heterocycle.
なくとも1個と、一般式( I )で示される有機残基か
ら選択される有機残基が少なくとも1個と前記選択され
た有機残基とは異なる一般式−N=H−Cp(III)(
式中、Cpはフェノール性OH基を有するカップラー残
基を示す、)で示される有機残基の少なくとも1個とが
同一分子内で結合基を介して結合してもよい置換もしく
は無置換の芳香族炭化水素環または芳香族複素環と結合
した構造を有するアゾ顔料を少なくとも1個とを含有す
る特許請求の範囲第1項または第2項または第3項記載
の電子写真感光体。(4) The photosensitive layer contains at least one azo pigment represented by the general formula (II) and at least one organic residue selected from the organic residues represented by the general formula (I). General formula -N=H-Cp(III) different from organic residue (
In the formula, Cp represents a coupler residue having a phenolic OH group.) A substituted or unsubstituted aromatic compound which may be bonded to at least one of the organic residues represented by ) through a bonding group within the same molecule. 3. The electrophotographic photoreceptor according to claim 1, which contains at least one azo pigment having a structure bonded to a group hydrocarbon ring or an aromatic heterocycle.
基を介して結合してもよい置換もしくは無置換の芳香族
炭化水素環または芳香族複素環、と結合した構造を有す
るアゾ顔料を含有する電荷発生層と電荷輸送層の少なく
とも3層からなる特許請求の範囲第1項記載の電子写真
感光体。(5) It has a structure in which the conductive layer and the organic residue represented by general formula (I) are bonded to a substituted or unsubstituted aromatic hydrocarbon ring or aromatic heterocycle which may be bonded via a bonding group. The electrophotographic photoreceptor according to claim 1, comprising at least three layers: a charge generation layer containing an azo pigment and a charge transport layer.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11677087A JP2558118B2 (en) | 1987-05-15 | 1987-05-15 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11677087A JP2558118B2 (en) | 1987-05-15 | 1987-05-15 | Electrophotographic photoreceptor |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63282745A true JPS63282745A (en) | 1988-11-18 |
JP2558118B2 JP2558118B2 (en) | 1996-11-27 |
Family
ID=14695297
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11677087A Expired - Fee Related JP2558118B2 (en) | 1987-05-15 | 1987-05-15 | Electrophotographic photoreceptor |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2558118B2 (en) |
-
1987
- 1987-05-15 JP JP11677087A patent/JP2558118B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2558118B2 (en) | 1996-11-27 |
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