JPH03174540A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH03174540A JPH03174540A JP31327189A JP31327189A JPH03174540A JP H03174540 A JPH03174540 A JP H03174540A JP 31327189 A JP31327189 A JP 31327189A JP 31327189 A JP31327189 A JP 31327189A JP H03174540 A JPH03174540 A JP H03174540A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- group
- general formula
- photosensitive layer
- charge
- 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 61
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000005647 linker group Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 39
- 239000000126 substance Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 230000035945 sensitivity Effects 0.000 abstract description 9
- 239000000758 substrate Substances 0.000 abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- -1 thiophenepyridine Chemical group 0.000 description 24
- 230000032258 transport Effects 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 210000003127 knee Anatomy 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000007788 liquid Substances 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
- 229910052711 selenium Inorganic materials 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 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
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000005018 casein Substances 0.000 description 3
- 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 3
- 235000021240 caseins Nutrition 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920001230 polyarylate Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 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 group 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
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 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
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 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 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound 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
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004970 halomethyl group Chemical group 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
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920002382 photo conductive polymer Polymers 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer 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
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-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 compound 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
- JPDUPGAVXNALOL-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetraphenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 JPDUPGAVXNALOL-UHFFFAOYSA-N 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-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
- 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
- YOPJQOLALJLPBS-UHFFFAOYSA-N 4,5-diphenyloxadiazole Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)ON=N1 YOPJQOLALJLPBS-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
- JZVZITXBBDBMAL-UHFFFAOYSA-N 9-ethyl-3-methylidene-2h-carbazole Chemical compound C=C1CC=C2N(CC)C3=CC=CC=C3C2=C1 JZVZITXBBDBMAL-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Chemical group C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RFLVJBXRTJRONX-UHFFFAOYSA-N N1C(CCC1)=O.N1C=CC2=CC=CC=C12 Chemical compound N1C(CCC1)=O.N1C=CC2=CC=CC=C12 RFLVJBXRTJRONX-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- VGMSBIBTURRWMF-UHFFFAOYSA-N anthracene-9,10-dione;phenanthrene-1,2-dione Chemical compound C1=CC=C2C(C=CC(C3=O)=O)=C3C=CC2=C1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 VGMSBIBTURRWMF-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SHTHWCQBJTUESB-UHFFFAOYSA-N ethyl hypofluorite Chemical group CCOF SHTHWCQBJTUESB-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は電子写真感光体に関し、詳しくは特定の構造を
膚するジスアゾ顔料を感光層中に含有する電子写真感光
体に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor containing a photosensitive layer containing a disazo pigment that exhibits a specific structure.
［従来の技術］
電子写真法は米国特許第２２９７６９１号明細書に開示
されるように画像露光の間に受けた照射量に応じてその
電気抵抗が変化する暗所で絶縁性の物質をコーティング
した支持体よりなる光導電性材料を用いる。[Prior Art] Electrophotography, as disclosed in U.S. Pat. No. 2,297,691, involves coating an insulating material in the dark, the electrical resistance of which changes depending on the amount of radiation received during image exposure. A photoconductive material consisting of a support is used.
この光導電性材料を用いた電子写真感光体に要求される
基本的な特性としては、■暗所で適当な電位に帯電でき
ること、■暗所において電荷の逸散が少ないこと、■光
照射によって速やかに電荷を逸散せしめ得ることなどが
挙げられる。The basic characteristics required of an electrophotographic photoreceptor using this photoconductive material are: ■ The ability to be charged to an appropriate potential in the dark, ■ Less dissipation of charge in the dark, and ■ The ability to be charged to an appropriate potential in the dark. For example, the charge can be quickly dissipated.
従来より、電子写真感光体としてはセレン、酸化亜鉛、
硫化カドミウムなどの無機光導電性化合物を主成分とす
る無機感光体が広く用いられてきた。しかし、これらは
■〜■の条件は満足するが、熱安定性、耐湿性、耐久性
などにおいて必ずしも満足し得るものではない０例えば
セレンは結晶化すると感光体としての特性が劣化してし
まうため、製造上も難しく、また熱や指紋などが原因と
なり結晶化し、感光体としての性能が劣化してしまう、
また硫化カドミウムでは耐湿性、酸化亜鉛では平滑性、
硬度、耐摩耗性に問題がある。さらに無機感光体の多く
は感光波長域が限定されている０例えばセレンでは感光
波長域は青色域であり、赤色域にはほとんど感度を示さ
ない、そのため感光性を長波長域に広げるために種々の
方法が提案されているが、感光波長域の選択には制約が
多い、酸化亜鉛あるいは硫化カドミウムを感光体として
用いる場合も、それ自体の感光波長域は狭く、種々の増
感剤の添加が必要である。Conventionally, electrophotographic photoreceptors have been made of selenium, zinc oxide,
Inorganic photoreceptors based on inorganic photoconductive compounds such as cadmium sulfide have been widely used. However, although these satisfy the conditions ■ to ■, they are not necessarily satisfactory in terms of thermal stability, moisture resistance, durability, etc. For example, when selenium crystallizes, its properties as a photoreceptor deteriorate. It is difficult to manufacture, and it also crystallizes due to heat and fingerprints, deteriorating its performance as a photoreceptor.
In addition, cadmium sulfide has moisture resistance, zinc oxide has smoothness,
There are problems with hardness and wear resistance. Furthermore, many inorganic photoreceptors have a limited photosensitive wavelength range. For example, selenium is sensitive to blue wavelengths and has almost no sensitivity to red. Therefore, various methods are used to extend photosensitivity to longer wavelength ranges. However, there are many restrictions on the selection of the sensitive wavelength range. Even when zinc oxide or cadmium sulfide is used as a photoreceptor, the sensitive wavelength range itself is narrow, and the addition of various sensitizers is difficult. is necessary.
これら無機感光体の宥する欠点を克服する目的で様々な
有機光導電性化合物を主成分とする電子写真感光体の開
発が盛んに行なわれている。In order to overcome the drawbacks of these inorganic photoreceptors, electrophotographic photoreceptors containing various organic photoconductive compounds as main components are being actively developed.
例えば特公昭５０−１０４９６号公報、米国特許第３４
８４２３７号明細書にはポリ−Ｎ−ビニルカルバゾール
と２．４．７−１リニトロフルオレノン−９−オンを含
宥する感光層を右する感光体、特公昭４８−２５６５８
号公報にはポリ−Ｎ−ビニルカルバゾールをピリリウム
塩系色素で増感したものなどがある。For example, Japanese Patent Publication No. 50-10496, U.S. Patent No. 34
No. 84237 describes a photoreceptor having a photosensitive layer containing poly-N-vinylcarbazole and 2.4.7-1 linitrofluorenone-9-one, Japanese Patent Publication No. 48-25658.
The publication discloses a product in which poly-N-vinylcarbazole is sensitized with a pyrylium salt dye.
これらの有機電子写真感光体は前記無機電子写真感光体
の欠点をある程度改善しているものの。Although these organic electrophotographic photoreceptors have improved the drawbacks of the inorganic electrophotographic photoreceptors to some extent.
概して光感度が低くなり、また繰り返し使用に適するも
のではなかった。In general, the photosensitivity was low and it was not suitable for repeated use.
これらの欠点を克服するために、近年、有機電子写真感
光体として様々な感光体が提案されているが、中でも光
を照射したとき電荷担体を発生する物質（以下、電荷発
生物質という）を含む層（以下、電荷発生層という）と
、電荷発生層が発生した電荷担体を受けいれてこれを搬
送する物質（以下、電荷輸送物質という）を主体とする
層（以下、電荷輸送層という）とからなる積層型の感光
体が従来の有機電子写真感光体に比べ、一般に感度が高
く、繰り返し使用に耐えるなどの点から一部実用に供さ
れている。In order to overcome these drawbacks, various photoreceptors have been proposed as organic electrophotographic photoreceptors in recent years. layer (hereinafter referred to as a charge generation layer) and a layer (hereinafter referred to as a charge transport layer) mainly consisting of a substance (hereinafter referred to as a charge transport substance) that accepts and transports charge carriers generated by the charge generation layer. Laminated type photoreceptors have been put into some practical use because they generally have higher sensitivity than conventional organic electrophotographic photoreceptors and can withstand repeated use.
このような有機光導電性化合物は、無機光導電性化合物
に比べて合成が容易で、しかも分子設計により可視光感
度に関しては感光波長域を比較的容易に変えることがで
きるため、感色性のコントロールができ、かつ、無公害
性で生産性、経済性も無機光導電性化合物に比べ格段に
優れていることから、近年、開発が競われ、感度、耐久
性など実用化のレベルに達しているものも少なくない。Such organic photoconductive compounds are easier to synthesize than inorganic photoconductive compounds, and the visible light sensitivity can be changed relatively easily in the wavelength range through molecular design. Since they are controllable, non-polluting, and far superior in terms of productivity and economy compared to inorganic photoconductive compounds, there has been a lot of competition in recent years to develop them, and they have reached the level of practical use in terms of sensitivity and durability. There are quite a few.
しかし、現在、耐久性、特に繰り返し使用した際の電位
の安定性、環境変動における電位変化の右無などにおい
てアモルファスシリコーンに代表される無機光導電性化
合物に比べると未だ劣るとことが少なくない。However, at present, they are still often inferior to inorganic photoconductive compounds such as amorphous silicone in terms of durability, especially potential stability during repeated use, and resistance to potential changes due to environmental changes.
［発明が解決しようとする課題］
本発明の目的は、新規な光導電性材料を提供すること、
可視域における実用的な高感度特性と繰り返し使用時の
安定した電位特性を有する電子写真感光体を提供するこ
とである。[Problems to be Solved by the Invention] An object of the present invention is to provide a novel photoconductive material;
An object of the present invention is to provide an electrophotographic photoreceptor having practical high sensitivity characteristics in the visible region and stable potential characteristics during repeated use.
［課題を解決する手段、作用］
本発明は、導電性支持体上に下記一般式（１）で示すジ
スアゾ顔料を含墳する感光層を有することを特徴とする
電子写真感光体から構成される。[Means for Solving the Problems, Effects] The present invention comprises an electrophotographic photoreceptor characterized by having a photosensitive layer containing a disazo pigment represented by the following general formula (1) on a conductive support. .
式中、Ａｒｃ、Ａｒ２およびＡｒ３は同一または異なっ
て、結合基を介して結合してもよい置換基を有してもよ
い芳香族炭化水素基または複素環基を示し、Ｚは酸素原
子または硫黄原子を示し、ＣＰｌおよびＣＲ２は同一ま
たは異なるフェノール性水酸基を有するカプラーＴｉｊ
ｃ基を示す。In the formula, Arc, Ar2 and Ar3 are the same or different and represent an aromatic hydrocarbon group or a heterocyclic group which may have a substituent which may be bonded via a bonding group, and Z is an oxygen atom or a sulfur atom. CPl and CR2 are couplers Tij having the same or different phenolic hydroxyl groups;
Indicates c group.
一般式（１）中、Ａｒ１ 、Ａｒ２およびＡｒ３の具体
例としては、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、ピレンなどの芳香族炭化水
素基、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、チアゾールなどの芳香族複素環基、
さらに上記芳香環を直接あるいは芳香族性基または非芳
香族性基で結合したもの、例えばトリフェニルメタン、
ジフェニルメタン、Ｎ−メチルジフェニルメタン、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スラキノン、ベンズアンスロン
、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。In general formula (1), specific examples of Ar1, Ar2, and Ar3 include aromatic hydrocarbon groups such as benzene, naphthalene, fluorene, phenanthrene, anthracene, and pyrene, furan, thiophenepyridine, indole, benzothiazole, carbazole, and acridone. , dibenzothiophene, benzoxazole, benzotriazole,
Aromatic heterocyclic groups such as oxadiazole and thiazole,
Furthermore, those in which the above-mentioned aromatic rings are bonded directly or with an aromatic group or a non-aromatic group, such as triphenylmethane,
Diphenylmethane, N-methyldiphenylmethane, biphenyl, terphenyl, binaphthyl, fluorenone, phenanthrenequinone anthraquinone, benzanthrone, diphenyloxadiazole, phenylbenzoxazole diphenylmethane, diphenylsulfone, diphenyl ether, benzophenone, stilbene.
ジスチリルベンゼン、テトラフェニル−ｐ−フェニレン
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 include distyrylbenzene, tetraphenyl-p-phenylenediamine, and tetraphenylbenzidine.
上記結合基を介して結合していてもよい芳香族炭化水素
基または複素環基が有してもよい置換基としては、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、プロポキシ、ブ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、水酸基シアノ基、トリフルオロメチルなどのハロ
メチル基などが挙げられる。Examples of substituents that the aromatic hydrocarbon group or heterocyclic group that may be bonded via the above-mentioned bonding group include alkyl groups such as methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, Examples include alkoxy groups such as butoxy, halogen atoms such as fluorine atoms, chlorine atoms, and bromine atoms, hydroxyl groups, cyano groups, and halomethyl groups such as trifluoromethyl.
ＣＰｌおよびＣＲ２の好ましい例としては、下記一般式
（２）〜（６）で示すカプラー残基が挙げられる。Preferred examples of CPl and CR2 include coupler residues represented by the following general formulas (2) to (6).
一般式
一般式（２）、（３）および（４）中、Ｘはベンゼン環
と縮合して置換基を右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、ベンズカルバゾール環、ジ
ベンゾフラン環などの多環芳香環または複素環を形成す
るのに必要な残基を示す。General Formulas In the general formulas (2), (3) and (4), Indicates the residues necessary to form a polycyclic aromatic ring or a heterocycle.
一般式（２）中のＺは酸素原子または硫黄原子を示し、
文は０または１の整数である。Z in general formula (2) represents an oxygen atom or a sulfur atom,
A statement is an integer of 0 or 1.
一般式（２）および（３）中の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。R1 and R2 in general formulas (2) and (3) are a hydrogen atom and an alkyl group which may have a substituent.
アリール基、アラルキル基、複素環基またはＲ１とＲ２
の結合する窒素原子を含む環状アミノ基を示す。Aryl group, aralkyl group, heterocyclic group or R1 and R2
represents a cyclic amino group containing a bonded nitrogen atom.
一般式（４）中のＲ３は水素原子、置換基を有してもよ
いアルキル基、アリール基、アラルキル基または複素環
基を示す。R3 in the general formula (4) represents a hydrogen atom, an alkyl group that may have a substituent, an aryl group, an aralkyl group, or a heterocyclic group.
一般式（５）中のＲ４は置換基を有してもよいアルキル
基、アリール基、アラルキル基または複素環基を示す。R4 in general formula (5) represents an alkyl group, an aryl group, an aralkyl group, or a heterocyclic group which may have a 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、ア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、アラルキ
ル基としてはベンジル、フェネチル、ナフチルメチルな
どの基、複素環基としては、ピリジル、チエニル、チア
ゾリル、カルバゾリル、ベンゾイミダゾリル、ベンゾチ
アゾリルなどの基、窒素原子を含む環状アミ７基とじて
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、カルバゾール、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などか
ら誘導される環状アミン基が挙げられる。The alkyl groups in the above expression include methyl, ethyl, propyl, butyl, etc., and the aryl groups include phenyl,
Groups such as diphenyl, naphthyl, and anthryl; aralkyl groups such as benzyl, phenethyl, and naphthylmethyl; heterocyclic groups such as pyridyl, thienyl, thiazolyl, carbazolyl, benzimidazolyl, and benzothiazolyl; and cyclic amino acids containing nitrogen atoms. Examples of the 7 groups include cyclic amine groups derived from pyrrole, pyrroline, pyrrolidine, pyrrolidone indole, indoline, carbazole, imidazole, pyrazole, pyrazoline, oxazinephenoxazine, and the like.
一般式（６）中のＹは、置換基を有してもよい２価の芳
香族炭化水素基ないしは窒素原子を環内に含む２価の複
素環基を示し、具体的には、ｏ −フェニレン、Ｏ−ナ
フチレン、ベリナフチレン、１．２−アンスリレン、３
，４−ピラゾールジイル、２，３−ピリジンジイル、４
，５−ピリジンジイル、６，７−インダゾールジイル、
６，７−キラリンジイルなどの基が挙げられる。Y in general formula (6) represents a divalent aromatic hydrocarbon group which may have a substituent or a divalent heterocyclic group containing a nitrogen atom in the ring, specifically, o- Phenylene, O-naphthylene, berinaphthylene, 1,2-antrylene, 3
, 4-pyrazolediyl, 2,3-pyridinediyl, 4
, 5-pyridinediyl, 6,7-indazolediyl,
Examples include groups such as 6,7-chiralindiyl.
さらにＲ１−Ｒ４，ＸおよぶＹの有してもよい置換基と
しては、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、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７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が挙げられる。Furthermore, as substituents that R1-R4,X and Y may have, alkyl groups such as methyl, ethyl, and propyl;
Alkoxy groups such as methoxy and ethoxy, fluorine atoms,
Examples include halogen atoms such as chlorine atom, bromine atom, and iodine atom, fulkylamino groups such as dimethylamino and diethylamino, phenylcarbamoyl groups, nitro groups, cyano groups, and halomethyl groups such as trifluoromethyl.
なお、一般式（１）中、ＣＰＩおよびＣＦ２が一般式（
２）、（３）または（４）であり、式中のＸがベンゼン
環と縮合してベンズカルバゾール環を形成しているカプ
ラー残基であるジスアゾ顔料は、その吸収域が近赤外領
域付近まで広がるため、半導体レーザー用の電荷発生材
料としても好適である。In addition, in the general formula (1), CPI and CF2 are represented by the general formula (
2), (3) or (4), in which X is a coupler residue condensed with a benzene ring to form a benzcarbazole ring, the disazo pigment has an absorption range near the near-infrared region. Therefore, it is suitable as a charge generating material for semiconductor lasers.
以下に一般式（１）で示すジスアゾ顔料の代表例を列挙
するが、本発明に用いる一般式（１）で示すジスアゾ顔
料はこれらに限定されるものではない。Representative examples of the disazo pigment represented by the general formula (1) are listed below, but the disazo pigment represented by the general formula (1) used in the present invention is not limited to these.
例示顔料（１）
Ｃｐｘ −Ｎ−Ｎ−＠−ＮＨＣＯ−＠−ＣＯＮＨ−＠−
Ｎ−Ｎ−ＣｐユＣＰ１．、ＣＦ２：
例示顔料
（２）
Ｃｐ□−Ｎ４ｓＨｃｏ−４かｃｏ＋ｕ＋−＠−Ｎ−Ｎ−
ｃ ｐ。Exemplary pigment (1) Cpx -N-N-@-NHCO-@-CONH-@-
N-N-CpyuCP1. , CF2: Exemplary pigment (2) Cp□-N4sHco-4 or co+u+-@-N-N-
c p.
ＣＰｌ 、 ０Ｐ２ ：
例示顔料
（３）
ｃｐ□−Ｎ−Ｎ七シ５Ｈｃｏ−＠−ｃｏｏ−＠−Ｎ−Ｎ
−ｃ ｐユＣＰＩ 、 ＣＦ２ ：
Ｃ又
例示顔料
（４）
Ｏｐｌ−Ｎ−Ｎ−＠＋ＮＨＣＳ−４テｃｓＮＨ４Ｎ−ｓ
−ｃ ｐユＣＰ１ 、 ＣＦ２ ：
例示顔料
（５）
Ｃｐｌ−Ｎ同（ツＮ ）ｌ Ｃ９−＠−ｃＳ Ｎ Ｈ（
ｃ矢Ｎ−Ｎ−Ｃｐ。CPl, 0P2: Exemplary pigment (3) cp□-N-N7 5Hco-@-coo-@-N-N
-c pyuCPI, CF2: C also exemplary pigment (4) Opl-N-N-@+NHCS-4tecsNH4N-s
-c pyu CP1, CF2: Exemplary pigment (5) Cpl-N (tsuN)l C9-@-cSN H(
c arrow N-N-Cp.
ＣＰｉ 、 ＣＦ２ ：
例示顔料（６）
ＣＰｌ−Ｎ−Ｎ−＠−Ｎ）ＩｃＯ登ｃＯＮ Ｈ−＠＞
Ｎ −Ｎ −ＣＰよＣＰＩ 、 ＣＦ２ ：
例示顔料（７）
ＣＰｌ 、 ＣＦ２ ：
例示顔料
（８）
Ｃｐ□−Ｎ−ＮへンＮＨＣＯ各Ｃ０ＮＨ各Ｎ冨Ｎ−ｃｐ
よａｐｔ 、 ＣＦ２ ：
例示顔料
（９）
ＣＰｌ 、 ＣＦ２ ：
例示顔料（１０）
ＣＰＩ 、 ＣＦ２ ：
例示顔料（１１）
ＣＰＩ 、 ＣＦ２ ：
例示顔料（１２）
ＣＰＩ 、 ＣＦ２ ：
例示顔料（１３）
ＣＰｌ 、 ＣＦ２ ：
Ｃえ
例示顔料（１
４）
例示顔料（１５）
ＣＰｌ 、 ＣＦ２ ：
例示顔料（１６）
ＣＰＩ 、 ＣＦ２ ：
例示顔料（１
７）
例示顔料（１８）
ＣＰｌ 、 ＣＦ２ ：
例示顔料（１９）
ＣＰｌ 、 ＣＦ２ ：
例示顔料（２０）
ＣＰＩ 、 ＣＦ２ ：
し入
例示顔料（２１）
ｃｐｔ 、 ＣＦ２ ：
例示顔料（２２）
ＣＰＩ 、 ＣＦ２ ：
例示顔料（２３）
ＣＰＩ 、 ＣＦ２ ：
例示顔料（２４）
ＣＰＩ 、 ＣＦ２ ：
例示顔料（２５）
ＣＰＩ
ＣＦ２
例示顔料（２６）
Ｃｐｌ 、 ＣＦ２ ：
例示顔料（２７）
Ｃｐｌ 、 ＣＦ２ ：
例示顔料（２８）
ＣＰＩ 、 ＣＦ２ ：
例示顔料（２９）
ＣＰＩ
ＣＦ２
例示顔料（３０）
Ｈ
ｃｐｔ 、 ＣＦ２ ニ
一般式（１）で示すジスアゾ顔料の一般的な製法につい
て説明する。CPi, CF2: Exemplary pigment (6) CPl-N-N-@-N) IcO CON H-@>
N-N-CP to CPI, CF2: Exemplary pigment (7) CPl, CF2: Exemplary pigment (8) Cp□-N-N NHCO each C0NH each N to N-cp
Yoapt, CF2: Exemplary pigment (9) CPl, CF2: Exemplary pigment (10) CPI, CF2: Exemplary pigment (11) CPI, CF2: Exemplary pigment (12) CPI, CF2: Exemplary pigment (13) CPl, CF2: Exemplary pigment (1 4) Exemplary pigment (15) CPl, CF2: Exemplary pigment (16) CPI, CF2: Exemplary pigment (1 7) Exemplary pigment (18) CPl, CF2: Exemplary pigment (19) CPl, CF2: Exemplary pigment (20) CPI, CF2: Injected exemplary pigment (21) cpt, CF2: Exemplary pigment (22) CPI, CF2: Exemplary pigment (23) CPI, CF2: Exemplary pigment (24) CPI, CF2: Exemplary pigment ( 25) CPI CF2 Exemplary Pigment (26) Cpl, CF2: Exemplary Pigment (27) Cpl, CF2: Exemplary Pigment (28) CPI, CF2: Exemplary Pigment (29) CPI CF2 Exemplary Pigment (30) H cpt, CF2 General formula A general method for producing the disazo pigment shown in (1) will be explained.
下記一般式（７）で示すジアミンを亜硝酸ソーダまたは
ニトロシル硫酸などの常法によりテトラゾニウム塩とし
、カプラー成分であるＣＰＩＣＰ２ と水系カップリン
グを行なうか、あるいは得られたテトラゾニウム塩をホ
ウフッ化塩などの安定な塩として取り出したのち、ジメ
チルホルムアミドなどの溶剤中で、前記カプラーとカッ
プリングすることにより容易に合成できる。The diamine represented by the following general formula (7) is made into a tetrazonium salt using a conventional method such as sodium nitrite or nitrosyl sulfate, and the resulting tetrazonium salt is subjected to aqueous coupling with the coupler component CPICP2, or the obtained tetrazonium salt is converted into a tetrazonium salt using a conventional method such as sodium nitrite or nitrosyl sulfate. It can be easily synthesized by extracting it as a stable salt and then coupling it with the above coupler in a solvent such as dimethylformamide.
合戊例（例示顔料（１）の合成）
３００ｍＡビーカーに水１５０ｍＪ１、濃塩酸２４ｍ１
（０，２７モル）を入れ、氷水浴で冷却しながら、構
造式
％式％
１３．１ｇ（０，０４１モル）を加え攪拌しつり液温を
３℃とした０次に亜硝酸ンーダ６．０ｇ（０，０８７モ
ル）を水１０ｍＭに溶かした液を液温を５°Ｃ以下に保
ちながら１０分間で滴下し、滴下終了後、同温度でさら
に３０分間攪拌した。Synthesis Example (Synthesis of Exemplary Pigment (1)) In a 300mA beaker, 150mJ1 of water and 24ml of concentrated hydrochloric acid
(0.27 mol) and while cooling in an ice water bath, 13.1 g (0.041 mol) of structural formula % was added and stirred, and the liquid temperature was adjusted to 3°C. A solution prepared by dissolving 0g (0,087 mol) in 10mM water was added dropwise over 10 minutes while keeping the liquid temperature below 5°C, and after the dropwise addition was completed, the mixture was stirred at the same temperature for an additional 30 minutes.
反応液にカーボンを加え、濾過した後に、ホウフッ化ン
ーダ１３．５ｇ（０，１２３モル）を水２０ｍ文に溶か
した液を傍下し、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 prepared by dissolving 13.5 g (0,123 mol) of borofluoride in 20 m of water was added to the mixture, and the precipitated borofluoride salt was collected by filtration, washed with water, and then vacuum-treated. Dry.
収量１５．０ｇ、収率７５％
次に、ＩＪＩビーカーにＮ、Ｎ−ジメチルホルムアミド
２００ｍＭを入れ、これに２−ヒドロキシ−３−ナフト
エ酸−２゛−フルオロアニリド５゜９１ｇ（０，０２モ
ル）を溶解し、液温を５°Ｃに冷却した後、先に得たホ
ウフッ化塩４．８８ｇ（０、０１モル）を溶解し、次い
でトリエチルアミン２．１４ｇ （０，０２１モル）を
１０分間で滴下し、２時間攪拌した後析出した顔料を慮
取しＮ、Ｎ−ジメチルホルムアミドで４回、水で３回洗
浄した後凍結乾燥した。Yield: 15.0 g, Yield: 75% Next, 200 mM of N,N-dimethylformamide was placed in an IJI beaker, and 5.91 g (0.02 mol) of 2-hydroxy-3-naphthoic acid-2'-fluoroanilide was added thereto. After cooling the liquid temperature to 5°C, 4.88 g (0.01 mol) of the borofluoride salt obtained earlier was dissolved, and then 2.14 g (0.021 mol) of triethylamine was added over 10 minutes. After the mixture was added dropwise and stirred for 2 hours, the precipitated pigment was collected, washed four times with N,N-dimethylformamide and three times with water, and then freeze-dried.
収量７．０９ｇ、収率８１．０％
元素分析 計算値（％）実測値（％）Ｃ７４，
１１７５，１２
Ｈ４，３６４，３Ｏ
Ｎ ９．６１ ９．６５一般式（１
）で示すジスアゾ顔料を含有する被膜は光導電性を示し
、電子写真感光体の感光層に用いることができる。Yield 7.09g, yield 81.0% Elemental analysis Calculated value (%) Actual value (%) C74,
1175,12 H4,364,3O N 9.61 9.65 General formula (1
A coating containing a disazo pigment shown in ) exhibits photoconductivity and can be used in a photosensitive layer of an electrophotographic photoreceptor.
本発明の電子写真感光体は、導電性支持体上に一般式（
１）で示すジスアゾ顔料を含有する感光層を有する。The electrophotographic photoreceptor of the present invention has the general formula (
It has a photosensitive layer containing the disazo pigment shown in 1).
感光層の形態は公知のいかなる形態を取っていてもかま
わないが、一般式（１）で示すジスアゾ顔料を含有する
感光層を電荷発生層とし、これに電荷輸送物質を含有す
る電荷輸送層を積層した機能分離型の感光層が特に好ま
しい。The form of the photosensitive layer may be any known form; however, a photosensitive layer containing a disazo pigment represented by general formula (1) is used as a charge generation layer, and a charge transport layer containing a charge transporting substance is added thereto. Laminated functionally separated photosensitive layers are particularly preferred.
電荷発生層は、一般式（１）で示すジスアゾ顔料を適当
な溶剤中でバインダー樹脂と共に分散した塗布液を、導
電性支持体上に公知の方法によって塗布することによっ
て形成することができ、その膜厚は例えば５７ｚｍ以下
、好ましくは０．１〜１．３ｇｍの薄膜層とすることが
望ましい。The charge generation layer can be formed by coating a coating solution in which a disazo pigment represented by the general formula (1) is dispersed together with a binder resin in a suitable solvent on a conductive support by a known method. It is desirable that the film thickness is, for example, 57 zm or less, preferably 0.1 to 1.3 gm.
この際用いられるバインダー樹脂は、広範な絶縁性樹脂
あるいは有機光導電性ポリマーから選択されるが、ポリ
ビニルブチラール、ポリビニルベンザール、ボリアリレ
ート、ポリカーボネート。The binder resin used in this case is selected from a wide variety of insulating resins or organic photoconductive polymers, including polyvinyl butyral, polyvinyl benzal, polyarylate, and polycarbonate.
ポリエステル、フェノキシ樹脂、セルロース系樹脂、ア
クリル樹脂、ポリウレタンなどが好ましくその使用量は
電荷発生層中の含有；（シで８０虫量％以下、好ましく
は４０重量％以下である。Polyester, phenoxy resin, cellulose resin, acrylic resin, polyurethane and the like are preferably used, and the amount used in the charge generation layer is 80% by weight or less, preferably 40% by weight or less.
また使用する溶剤は前記の樹脂を溶解し、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 used is preferably selected from those that dissolve the resin described above but do not dissolve the charge transport layer or undercoat layer described later.
具体的には、テトラヒドロフラン、１．４−ジオキサン
などのエーテル類、シクロヘキサノン、メチルエチルケ
トンなどのケトン類、Ｎ、Ｎ−ジメチルホルムアミドな
どのアミド類、酢酸メチル酢酸エチルなどのエステル類
、トルエン、キシレン、クロロベンゼンなどの芳香族類
、メタノール、エタノール、２−プロパツールなどのア
ルコール類、クロロホルム、塩化メチレン、ジクロルエ
チレン、四塩化炭素、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など挙げられる。Specifically, ethers such as tetrahydrofuran and 1,4-dioxane, ketones such as cyclohexanone and methyl ethyl ketone, amides such as N,N-dimethylformamide, esters such as methyl acetate and ethyl acetate, toluene, xylene, and chlorobenzene. Examples include aromatics such as methanol, ethanol, alcohols such as 2-propanol, and aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, and trichlorethylene.
電荷輸送層は電荷発生層の上または下に積層され、電界
の存在下電荷発生層から電荷キャリアを受取り、これを
輸送する機能を有している。The charge transport layer is laminated above or below the charge generation layer, and has the function of receiving charge carriers from the charge generation layer in the presence of an electric field and transporting them.
電荷輸送層は電荷輸送物質を必要に応じて適当なバイン
ダー樹脂と共に溶剤中に溶解し塗布することによって形
成され、その膜厚は一般的には５〜４０ｐｍであるが８
〜３０ＩＬｍが好ましい。The charge transport layer is formed by dissolving a charge transport material in a solvent together with a suitable binder resin as necessary and applying the film, and the film thickness is generally 5 to 40 pm, but 8.
~30 ILm is preferred.
電荷輸送物質は電子輸送性物質と正孔輸送性物質があり
、電子輸送性物質としては、例えば２゜４．７−ドリニ
トロフルオレノン、２，４，５゜７−チトラニトロフル
オレノン、クロラニル、テトラシアノキノジメタンなど
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
たものなどが挙げられる。Charge transporting substances include electron transporting substances and hole transporting substances. Examples of electron transporting substances include 2゜4,7-dolinitrofluorenone, 2,4,5゜7-titranitrofluorenone, chloranil, and tetranitrofluorenone. Examples include electron-withdrawing substances such as cyanoquinodimethane, and polymerization of these electron-withdrawing substances.
正孔輸送性物質としてはピレン、アントラセンなどの多
環芳香族化合物、カルバゾール系、インドール系、イミ
ダゾール系、オキサゾール系、チアゾール系、オキサジ
アゾール系、ピラゾール系ピラゾリン系、チアジアゾー
ル系、トリアゾール系化合物などの複素環化合物、ｐ−
ジェチルアミノベンズアルデヒド−Ｎ、Ｎ−ジフェニル
ヒドラゾン、Ｎ、Ｎ−ジフェこルヒドラジノー３−メチ
リデン−９−エチルカルバゾールなどのヒドラゾン系化
合物、α−フェニル−４’−Ｎ、Ｎ−ジフェニルアミノ
スチルベン、５− （４−（ジ−ｐ−トリルアミノ）ベ
ンジリデン］ −５Ｈ−ジベンゾ［ａ 、 ｄ］ シク
ロヘプテンなどのスチリル系化合物、ベンジジン系化合
物、トリアリールメタン系化合物、トリフェニルアミン
あるいは、これらの化合物から成る基を主鎖または側鎖
に有するポリマー（例えばポリ−Ｎ−ビニルカルバゾー
ル、ポリビニルアントラセンなど）が挙げられる。Hole-transporting substances include polycyclic aromatic compounds such as pyrene and anthracene, carbazole-based, indole-based, imidazole-based, oxazole-based, thiazole-based, oxadiazole-based, pyrazole-based pyrazoline-based, thiadiazole-based, triazole-based compounds, etc. heterocyclic compound, p-
Hydrazone-based compounds such as dietylaminobenzaldehyde-N,N-diphenylhydrazone, N,N-diphecolhydrazino 3-methylidene-9-ethylcarbazole, α-phenyl-4'-N,N-diphenylaminostilbene, 5- (4-(di-p-tolylamino)benzylidene] -5H-dibenzo[a, d] A styryl compound such as cycloheptene, a benzidine compound, a triarylmethane compound, triphenylamine, or a group consisting of these compounds) Examples include polymers having it in the main chain or side chain (eg, poly-N-vinylcarbazole, polyvinylanthracene, etc.).
これらの有ｖ１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 v1 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
インダーを用いることができ、具体的には、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、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、
ポリビこルアントラセンなどの有機光導電性ポリマーな
どが挙げられる。When the charge transport material does not have film-forming properties, an appropriate binder can be used, specifically, acrylic resin, polyarylate, polyester, polycarbonate, polystyrene, acrylonitrile-styrene copolymer, polyacrylamide, polyamide, chlorine. Insulating resin such as rubber or poly-N-vinylcarbazole,
Examples include organic photoconductive polymers such as polyvinyl anthracene.
感光層が形成される導電性支持体としては、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、チ
タン、ニッケル、インジウム、金や白金などが用いられ
る。またこうした金属あるいは合金を、真空蒸着法によ
って被膜形成したプラスチック（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、アクリル樹脂など）や、導電性粒子（例えば
カーボンブラック、銀粒子など）を適当なバインダー樹
脂と共にプラスチックまたは金属基板上に被覆した支持
体あるいは導電性粒子をプラスチックや紙に含浸した支
持体などを用いることができる。Examples of the conductive support on which the photosensitive layer is formed include aluminum, aluminum alloy, copper, zinc stainless steel, titanium, nickel, indium, gold, and platinum. In addition, plastics (e.g. polyethylene,
Polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, etc.) or conductive particles (e.g. carbon black, silver particles, etc.) are coated on a plastic or metal substrate together with a suitable binder resin, or conductive particles are coated on a plastic or metal substrate. A support such as paper impregnated can be used.
導電性支持体と感光層の中間にバリヤー機能と接着機能
をもつ下引き層を設けることもできる。An undercoat layer having barrier and adhesive functions can also be provided between the conductive support and the photosensitive layer.
下引き層はカゼイン、ポリビニルアルコール、ニトロセ
ルロース、ポリアミド（ナイロン６、ナイロン６６、ナ
イロン６１Ｏ１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、酸化アルミニウムなどに
よって形成できる。The undercoat layer can be formed of casein, polyvinyl alcohol, nitrocellulose, polyamide (nylon 6, nylon 66, nylon 61O1 copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, aluminum oxide, or the like.
下引き層の膜厚は５７ｇｍ以下、好ましくは０゜１〜３
ルｍが適当である。The thickness of the undercoat layer is 57 gm or less, preferably 0°1-3
Le m is appropriate.
本発明の別の具体例として、一般式（１）で示すジスア
ゾ顔料と電荷輸送物質を同一層に含有させた電子写真感
光体を挙げることができる。Another specific example of the present invention is an electrophotographic photoreceptor containing a disazo pigment represented by general formula (1) and a charge transporting substance in the same layer.
この際、電荷輸送物質としてポリ−Ｎ−ビニルカルバゾ
ールとトリニトロフルオレノンからなる電荷移動錯体を
用いることもできる。At this time, a charge transfer complex consisting of poly-N-vinylcarbazole and trinitrofluorenone can also be used as the charge transport substance.
この例の電子写真感光体は、一般式（１）で示すジスア
ゾ顔料と電荷移動錯体を適当な樹脂溶液中に分散させた
液を塗布乾燥して形成することができる。The electrophotographic photoreceptor of this example can be formed by coating and drying a solution in which a disazo pigment represented by general formula (1) and a charge transfer complex are dispersed in a suitable resin solution.
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）で示すジスアゾ顔料の結晶形は結晶質であっても
非晶質であってもよい。The pigment used in any electrophotographic photoreceptor may be a disazo pigment represented by the general formula (1), and the crystal form thereof may be crystalline or amorphous.
また一般式（１）で示すジスアゾ顔料を２種類以上組み
合せたり、公知の電荷発生物質と組み合せて使用するこ
とも可能である。It is also possible to use a combination of two or more kinds of disazo pigments represented by the general formula (1), or to use them in combination with a known charge-generating substance.
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、レーザービームプリンターＣＲＴプリンター
、ＬＥＤプリンター、液晶プリンター、レーザー製版な
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 beam printers, CRT printers, LED printers, liquid crystal printers, and laser plate making.
［実施例］
実施例１〜１５
アルミニウム支持体上にメトキシメチル化ナイロン（平
均分子量３万２千）５ｇとアルコール可溶性共重合ナイ
ロン（平均分子量２万９千）１０ｇをメタノール９５［
に溶解した液をマイヤーバーで塗布し、乾燥後の膜厚が
Ｉｇｍの下引き層を設けた。[Example] Examples 1 to 15 5 g of methoxymethylated nylon (average molecular weight: 32,000) and 10 g of alcohol-soluble copolymerized nylon (average molecular weight: 29,000) were placed on an aluminum support in 95 g of methanol.
A solution dissolved in was applied with a Mayer bar to provide an undercoat layer having a thickness of Igm after drying.
次に、例示顔料（１）の５ｇをシクロヘキサノン９５ｍ
Ｊｌにブチラール樹脂（ブチラール化度６３モル％）２
ｇを溶かした液に加え、サンドミルで２０時間分散した
。この分散液を先に形成した下引き層の上に乾燥後の膜
厚が０．２ｐｍ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, 5 g of exemplified pigment (1) was added to 95 m of cyclohexanone.
Butyral resin (butyralization degree 63 mol%) 2 to Jl
g was added to the dissolved liquid and dispersed in a sand mill for 20 hours. This dispersion was applied onto the previously formed undercoat layer using a Mayer bar so that the film thickness after drying was 0.2 pm, and dried to form a charge generation layer.
次に、下記構造式のヒドラゾン化合物５ｇとポリメチル
メタクリレート（数平均分子量１０万）５ｇをトルエン
４０ｍＭに溶解し、これを電荷発生層の上にマイヤーバ
ーで塗布乾燥し、膜厚が２０．ｗｍの電荷輸送層を形威
し、実施例１の電子写真感光体を作成した。Next, 5 g of a hydrazone compound having the following structural formula and 5 g of polymethyl methacrylate (number average molecular weight: 100,000) were dissolved in 40 mM of toluene, and this was applied onto the charge generation layer using a Mayer bar and dried to give a film thickness of 20. An electrophotographic photoreceptor of Example 1 was prepared by forming a charge transport layer of Wm.
例示顔料（１）に代えて下記の例示顔料を用い他の条件
は実施例１と同様にして、実施例２〜１５に対応する電
子写真感光体を作成した。Electrophotographic photoreceptors corresponding to Examples 2 to 15 were prepared using the following exemplified pigments in place of exemplified pigment (1) and in the same manner as in Example 1 except for the other conditions.
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（川口電機■製Ｍｏｄｅｌ ５ｒ−４２８）を
用いて一５ＫＶでコロナ帯電し、暗所で１秒間保持した
後、照度１０ルツクスで露光し、帯電特性を評価した。The electrophotographic photoreceptor thus prepared was corona charged at 15 KV using an electrostatic copying paper tester (Model 5r-428 manufactured by Kawaguchi Electric), held in a dark place for 1 second, and then charged at an illumination intensity of 10 lux. It was exposed to light and the charging characteristics were evaluated.
帯電特性としては表面電位（ＶＱ ）と１秒間暗減衰さ
せた時の電位をｌ／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 (VQ) and the exposure amount (El
/2) was measured.
結果を示す。Show the results.
Ｖ −Ｖ Ｅｌ／２ １ｕｘ＊５ｅｃ１
（１） ６１０ ２．
６２ （３） ５９０ ２
．５３ （４） ６００
２．８４ （，７） ６００
３．５５ （９） ５９
５ ３．ｔ６ （１２） ６
００ ３．２７ （１６）
６０５ ２．４８ （１７）
６１０ ２．８９ （１８）
５９５ ２．７１０ （１９）
５９５ ３．２１ ｔ （２
２） ５９０ ３．３１２
（２４） ６００ ３．３１３
（２６） ６００ ３．２１４
（２７） ５９５ ３．４１
５ （２８） ６０５ ３．
５比較例１〜４
下記構造式のジスアゾ顔料を用いた他は、例１と同様に
して電子写真感光体を作成し、例１と同様に帯電特性を
評価した。V −V El/2 1ux*5ec1
(1) 610 2.
62 (3) 590 2
．． 53 (4) 600
2.84 (,7) 600
3.55 (9) 59
5 3. t6 (12) 6
00 3.27 (16)
605 2.48 (17)
610 2.89 (18)
595 2.710 (19)
595 3.21 t (2
2) 590 3.312
(24) 600 3.313
(26) 600 3.214
(27) 595 3.41
5 (28) 605 3.
5 Comparative Examples 1 to 4 Electrophotographic photoreceptors were prepared in the same manner as in Example 1, except that a disazo pigment having the following structural formula was used, and the charging characteristics were evaluated in the same manner as in Example 1.
結果を示す。Show the results.
（比較例１）
比較顔料（１）
実施
実施
ｃ ｐ −Ｎ ＝ Ｎ−＠−ＣＯＮ Ｈ−＠−Ｎ −Ｎ
−ＣＰ（比較例２）
比較顔料（２）
？
Ｃｐ −Ｎ −Ｎ−＠／−Ｃ舎Ｎ雪Ｎ−ｃｐ（比較例３
）
比較顔料（３）
（比較例４）
比較顔料（４）
Ｏｐ−Ｎ−Ｎ−ｏ−ＣｗＣ−＠−Ｎ−Ｎ−Ｏｐ１
（１） ５８０ ５．６２
（２） ５７０ ５．２３
（３） ５７５ ６．１４
（４） ５８５ ６．
３この結果から、本発明の電子写真感光体は、いずれも
十分な帯電能と十分な感度を有していることが分る。(Comparative Example 1) Comparative Pigment (1) Implementation c p -N = N-@-CON H-@-N -N
-CP (Comparative Example 2) Comparative pigment (2)? Cp -N -N-@/-C building N snow N-cp (Comparative example 3
) Comparative pigment (3) (Comparative example 4) Comparative pigment (4) Op-N-N-o-CwC-@-N-N-Op1
(1) 580 5.62
(2) 570 5.23
(3) 575 6.14
(4) 585 6.
3 From these results, it can be seen that all the electrophotographic photoreceptors of the present invention have sufficient charging ability and sufficient sensitivity.
実、施例１，２．７および１０で作成した電子写真感光
体を用い、繰り返し使用時の明部電位と暗部電位の変動
を利足した。Actually, the electrophotographic photoreceptors prepared in Examples 1, 2.7, and 10 were used to take advantage of fluctuations in bright area potential and dark area potential during repeated use.
方法としては、−５，６ｋＶのコロナ帯電器、露光光学
系、現像器、転写帯電器、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貼り付けた
。この複写機はシリンダーの駆動に伴ない転写紙上に画
像が得られる構成になっている。As for the method, it was attached to the cylinder of an electrophotographic copying machine equipped with a -5.6 kV corona charger, an exposure optical system, a developer, a transfer charger, a static elimination exposure optical system, and a cleaner. This copying machine is configured to produce an image on transfer paper as a cylinder is driven.
この複写機を用いて、初期の暗部電位Ｖｏと明部電位Ｖ
Ｌをツレぞれ一６００Ｖ、−１００Ｖ付近に設定し、５
千回繰り返し使用した際の暗部電位と明部電位を測定し
た。Using this copying machine, the initial dark potential Vo and bright potential V
Set L to around 600V and -100V respectively, and
The dark potential and bright potential were measured after repeated use 1,000 times.
結果を示す。Show the results.
１６ １ Ｂｏｏ １１０
５９０ １８０１７ ２
１３１０ １２０ ５９０ １７０１８
７ ＋３１０ ＋２０
．８００ １８０１９ １０
５９０ １００ ５８０ １５０実施例
２０
実施例１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７０ｍ文に溶解
して調製した塗布液を乾燥後の膜厚が１０ｇ／ｍ２とな
るように塗布し、乾燥した。16 1 Boo 110
590 18017 2
1310 120 590 17018
7 +310 +20
．． 800 18019 10
590 100 580 150 Example 20 On the charge generation layer prepared in Example 1, 5 g of 2,4.7-dolinitro-9-fluorenone and poly-4,4°-dioxydiphenyl-2,2-propane carbonate ( A coating solution prepared by dissolving 5 g (molecular weight: 300,000) in 70 ml of tetrahydrofuran was applied to give a film thickness of 10 g/m 2 after drying, and dried.
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Ｃ帯電特性を測定した。The charging characteristics of the electrophotographic photoreceptor thus prepared were measured in the same manner as in Example 1 using Method C.
ただし、帯電は正帯電とした。結果を示す。However, the charging was positive. Show the results.
ｖｏ ：＋６００Ｖ
Ｅｌ／２：３．７Ｊ１ｕｘ ・ ｓｅｃ実施例２１
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０．５ｇｍのポリビニルアルコールの下引
き層を形成した。vo:+600V El/2:3.7J1ux・sec Example 21 A polyvinyl alcohol undercoat layer having a thickness of 0.5 gm was formed on the aluminum surface of an aluminum vapor-deposited polyethylene terephthalate film.
この上に実施例１で用いたジスアゾ顔料の分散液をマイ
ヤーバーで塗布乾燥し、膜厚０．５ｇｍの電荷発生層を
形成した。On top of this, the dispersion of the disazo pigment used in Example 1 was applied using a Mayer bar and dried to form a charge generation layer with a thickness of 0.5 gm.
次いで、
下記構造式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をテトラヒドロフラン７
０ｍ文に溶かした液を電荷発生層の上に塗布乾燥して、
膜厚が１０ｇｍの電荷輸送層を形成した。Next, 5 g of a pyrazoline compound with the following structural formula and polyarylate (bisphenol A and terephthalic acid)
5 g of inphthalic acid condensation polymer) and 7 g of tetrahydrofuran
Apply the solution dissolved in 0m on the charge generation layer and dry it.
A charge transport layer having a thickness of 10 gm was formed.
こうして作成した電子写真感光体の帯電特性と耐久特性
を実施例１と実施例１６と同様の方法によって評価した
。結果を示す。The charging characteristics and durability characteristics of the electrophotographic photoreceptor thus prepared were evaluated in the same manner as in Examples 1 and 16. Show the results.
Ｖｏ ニー７００Ｖ
Ｅｌ／２ ： １．０ｕｕｘ＊ ｓｅｃ耐久特性
初 期
ＶＤ ニー６００Ｖ ＶＬ ニー１０５Ｖ５千枚酎久
後
Ｖｏ ニー５８０Ｖ ＶＬ ニー１６
０Ｖこの結果から、感度もよく、耐久使用時の電位安定
性も良好であることが分る。Vo knee 700V El/2: 1.0uux* sec Durability characteristics Initial VD knee 600V VL knee 105V5 after 1,000 pieces of sake Vo knee 580V VL knee 16
0V This result shows that the sensitivity is good and the potential stability during long-term use is also good.
実施例２２
厚さ１００ｇｍ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０．５μｍの下引き層を形
成した。Example 22 An ammonia aqueous solution of casein was applied onto an aluminum plate with a thickness of 100 gm and dried to form a subbing layer with a thickness of 0.5 μm.
次に、２，４．７−１リニトロ−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［３０万
）５ｇをテトラヒドロフラン７０ｍ文に溶解して電荷移
動錯体化合物を調製した。Next, 5 g of 2,4.7-1linitro-9-fluorenone
A charge transfer complex compound was prepared by dissolving 5 g of poly-N-vinylcarbazole (number average molecule [300,000]) in 70 m of tetrahydrofuran.
この電荷移動錯体化合物と例示顔料（９）を１ｇ、ポリ
エステル（商品名バイロン、東洋紡績■製）５ｇをテト
ラヒドロフラン７０ｍ１に溶解した液に加え、分散した
。この分散液を下引き層の上に塗布し、乾燥して１２７
ｚｍの感光層を形成した。This charge transfer complex compound, 1 g of Exemplary Pigment (9), and 5 g of polyester (trade name: Vylon, manufactured by Toyobo Co., Ltd.) were dissolved in 70 ml of tetrahydrofuran and dispersed. This dispersion was applied onto the undercoat layer and dried to 127
A photosensitive layer of zm was formed.
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。Example 1 Charging characteristics of the electrophotographic photoreceptor thus prepared
Measured using the same method.
ただし、帯電は正帯電とした− ＃Ａ央を示十−ｖｏ
：＋６００Ｖ
Ｅｌ／２：３．５Ｍｕｘ ＠ ｓｅｃ実施例２３
実施例２２で用いたカゼイン層を施したアルミニウム支
持体上に実施例１と同様の電荷輸送層と電荷発生層を順
次積層し、層構成を相違する他は実施例１と全く同様に
して電子写真感光体を作成し、同様に帯電特性を測定し
た。However, the charging was made positive - #A center is indicated as 10-vo
: +600V El/2:3.5Mux @ sec Example 23 The same charge transport layer and charge generation layer as in Example 1 were sequentially laminated on the casein layer-coated aluminum support used in Example 22 to form a layer structure. An electrophotographic photoreceptor was prepared in exactly the same manner as in Example 1 except for the following differences, and the charging characteristics were measured in the same manner.
ただし、帯電は正帯電とした。結果を示す。However, the charging was positive. Show the results.
ｖｏ ：＋６００Ｖ
Ｅｌ／２ ： ４．０１ｕＸ−ｓｅｃ
［発明の効果］
本発明の電子写真感光体は、感光層に特定構造のジスア
ゾ顔料を用いることにより、感光層内部におけるキャリ
アの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ることが推定され、高感度で繰り
返し使用時における電位安定性に優れた電子写真感光体
である。vo: +600V El/2: 4.01uX-sec [Effects of the Invention] The electrophotographic photoreceptor of the present invention uses a disazo pigment with a specific structure in the photosensitive layer, thereby improving carrier generation efficiency or carrier transport inside the photosensitive layer. It is estimated that one or both of the efficiency is improved, and the electrophotographic photoreceptor has high sensitivity and excellent potential stability during repeated use.
Claims (1)
顔料を含有する感光層を有することを特徴とする電子写
真感光体。 一般式 ▲数式、化学式、表等があります▼（１） 式中、Ａｒ＿１、Ａｒ＿２およびＡｒ＿３は同一または
異なって、結合基を介して結合してもよい置換基を有し
てもよい芳香族炭化水素基または複素環基を示し、Ｚは
酸素原子またほ硫黄原子を示し、Ｃｐ＿１およびＣｐ＿
２は同一または異なるフェノール性水酸基を有するカプ
ラー残基を示す。[Scope of Claims] 1. An electrophotographic photoreceptor comprising a photosensitive layer containing a disazo pigment represented by the following general formula (1) on a conductive support. General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (1) In the formula, Ar_1, Ar_2 and Ar_3 are the same or different and are aromatic carbonized compounds that may have a substituent that may be bonded via a bonding group. represents a hydrogen group or a heterocyclic group, Z represents an oxygen atom or a sulfur atom, Cp_1 and Cp_
2 represents a coupler residue having the same or different phenolic hydroxyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1313271A JP2652450B2 (en) | 1989-12-04 | 1989-12-04 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1313271A JP2652450B2 (en) | 1989-12-04 | 1989-12-04 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03174540A true JPH03174540A (en) | 1991-07-29 |
| JP2652450B2 JP2652450B2 (en) | 1997-09-10 |
Family
ID=18039200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1313271A Expired - Fee Related JP2652450B2 (en) | 1989-12-04 | 1989-12-04 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2652450B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5344736A (en) * | 1990-10-12 | 1994-09-06 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Disazo electrophotographic photoreceptor |
| WO2002057211A1 (en) * | 2001-01-16 | 2002-07-25 | Guilford Pharmaceuticals, Inc. | Symmetrically disubstituted aromatic compounds and pharmaceutical compositions for inhibiting poly (adp-ribose) glycohydrolase, and methods for their use |
| WO2013129015A1 (en) * | 2012-02-29 | 2013-09-06 | 保土谷化学工業株式会社 | Charge control agent and toner using same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03120553A (en) * | 1989-10-04 | 1991-05-22 | Konica Corp | Electrophotographic sensitive body |
-
1989
- 1989-12-04 JP JP1313271A patent/JP2652450B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03120553A (en) * | 1989-10-04 | 1991-05-22 | Konica Corp | Electrophotographic sensitive body |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5344736A (en) * | 1990-10-12 | 1994-09-06 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Disazo electrophotographic photoreceptor |
| WO2002057211A1 (en) * | 2001-01-16 | 2002-07-25 | Guilford Pharmaceuticals, Inc. | Symmetrically disubstituted aromatic compounds and pharmaceutical compositions for inhibiting poly (adp-ribose) glycohydrolase, and methods for their use |
| WO2013129015A1 (en) * | 2012-02-29 | 2013-09-06 | 保土谷化学工業株式会社 | Charge control agent and toner using same |
| JP5329010B1 (en) * | 2012-02-29 | 2013-10-30 | 保土谷化学工業株式会社 | Charge control agent and toner using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2652450B2 (en) | 1997-09-10 |
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