JPS63180957A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS63180957A JPS63180957A JP1133187A JP1133187A JPS63180957A JP S63180957 A JPS63180957 A JP S63180957A JP 1133187 A JP1133187 A JP 1133187A JP 1133187 A JP1133187 A JP 1133187A JP S63180957 A JPS63180957 A JP S63180957A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formulas
- tables
- formula
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000049 pigment Substances 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 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 30
- 239000000126 substance Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000758 substrate Substances 0.000 abstract description 8
- 230000035945 sensitivity Effects 0.000 abstract description 6
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- 239000010408 film Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000005018 casein Substances 0.000 description 6
- 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 6
- 235000021240 caseins Nutrition 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000002800 charge carrier Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 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
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000002245 particle Substances 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
- 229920000728 polyester Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 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
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000003127 knee Anatomy 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 230000003287 optical effect Effects 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
- 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
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 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
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QSKGBYWLRDVOLD-UHFFFAOYSA-N 2-methylidene-9h-fluoren-1-one Chemical compound C1=CC=C2C(C=CC(C3=O)=C)=C3CC2=C1 QSKGBYWLRDVOLD-UHFFFAOYSA-N 0.000 description 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
- JJQYAPNPXXKRDF-UHFFFAOYSA-N 4-(2,3-dihydro-1h-pyrazol-3-yl)-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1C=CNN1 JJQYAPNPXXKRDF-UHFFFAOYSA-N 0.000 description 1
- UZGVMZRBRRYLIP-UHFFFAOYSA-N 4-[5-[4-(diethylamino)phenyl]-1,3,4-oxadiazol-2-yl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(CC)CC)O1 UZGVMZRBRRYLIP-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- LSZJZNNASZFXKN-UHFFFAOYSA-N 9-propan-2-ylcarbazole Chemical compound C1=CC=C2N(C(C)C)C3=CC=CC=C3C2=C1 LSZJZNNASZFXKN-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- QTADRORPFKINAU-UHFFFAOYSA-N CCN(CC)C1=CC=C(C=C(CC2=CC=CC=C2)C2=CCN(C3=CC=CC=C3)N2)C=C1 Chemical class CCN(CC)C1=CC=C(C=C(CC2=CC=CC=C2)C2=CCN(C3=CC=CC=C3)N2)C=C1 QTADRORPFKINAU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GIYXAJPCNFJEHY-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine hydrochloride (1:1) Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 GIYXAJPCNFJEHY-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
- 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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-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
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 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
- 230000004888 barrier function Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- MGIAHHJRDZCTHG-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 MGIAHHJRDZCTHG-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229940117389 dichlorobenzene Drugs 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
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 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
- 230000005525 hole transport Effects 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- COHYTHOBJLSHDF-BUHFOSPRSA-N indigo dye Chemical compound N\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-BUHFOSPRSA-N 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 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
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- SUJMFQYAKKPLSH-UHFFFAOYSA-N n-[[4-(diethylamino)phenyl]methylideneamino]-n-phenylnaphthalen-1-amine Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 SUJMFQYAKKPLSH-UHFFFAOYSA-N 0.000 description 1
- XRWSIBVXSYPWLH-UHFFFAOYSA-N n-phenyl-n-[(4-pyrrolidin-1-ylphenyl)methylideneamino]aniline Chemical compound C1CCCN1C(C=C1)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 XRWSIBVXSYPWLH-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene 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
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 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
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 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
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0687—Trisazo dyes
- G03G5/0688—Trisazo dyes containing hetero rings
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、詳しくは特定の構造のトリス
アゾ顔料よりなる宥機光導電性物質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 [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more particularly, to an electrophotographic photoreceptor having a photosensitive layer containing a photoconductive material made of a trisazo pigment having a specific structure. .
［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
機光導電体を感光層に含有する電子写真感光体はよく知
られている。一方、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、ヒドラゾ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、インジゴ染料、
チオインジゴ染料、スクエアリック酸メチン染料などの
有機光導電体が開発されてきた。さらに、例えば米国特
許第４１２３２７０号明細書、米国特許第４２４７６１
４号明細書、米国特許第４２５１６１３号明細書、米国
特許第４２５６８２１号明細書などに開示されていると
おり、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のジスアゾ顔料を用
いた電子写真感光体が知られている。[Prior Art] Electrophotographic photoreceptors containing inorganic photoconductors such as selenium, cadmium sulfide, and zinc oxide in the photosensitive layer are well known. On the other hand, organic photoconductive polymers such as poly-N-vinylcarbazole and polyvinylanthracene, low-molecular organic photoconductors such as carbazole, anthracene, pyrazolines, oxadiazoles, and hydrazones, phthalocyanine pigments, azo pigments, indigo dye,
Organic photoconductors such as thioindigo dyes and methine squaric acid dyes have been developed. Further, for example, US Pat. No. 4,123,270, US Pat. No. 4,24761
As disclosed in U.S. Pat. No. 4, U.S. Pat. No. 4,251,613, U.S. Pat. Electrophotographic photoreceptors using disazo pigments are known.
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り浸漬コーティングに
よる塗工法を用いて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、しかも適当な波長域に光導電
性を呈する宥機顔料を選択できるという利点がある反面
、感度と繰返し使用に対する耐久性に難点があるため、
これまで実用化されているものはごく僅かである。An electrophotographic photoreceptor using such an organic photoconductor can be produced using a coating method using dip coating by appropriately selecting a binder, making it possible to provide an extremely highly productive and inexpensive photoreceptor. Although it has the advantage of being able to select a clearing pigment that exhibits photoconductivity in the wavelength range, it has drawbacks in terms of sensitivity and durability against repeated use.
Only a few have been put into practical use so far.
［発明が解決しようとする問題点］
本発明の目的は新規な有機光導電体を感光層に含有する
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 an electrophotographic photoreceptor containing a novel organic photoconductor in its photosensitive layer.
さらに別の目的は実用的な高感度を有し、かつ繰返し使
用後も安定な帯電特性を示す電子写真感光体を提供する
ことにある。Still another object is to provide an electrophotographic photoreceptor that has high sensitivity for practical use and exhibits stable charging characteristics even after repeated use.
［問題点を解決する手段、作用］
本発明は、導電性基体上に設けられた感光層に下記一般
式（１）で示されるトリスアゾ顔料の少なくとも一種を
光導電体として含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 and effects for solving the problems] The present invention is characterized in that a photosensitive layer provided on a conductive substrate contains at least one trisazo pigment represented by the following general formula (1) as a photoconductor. It consists of an electrophotographic photoreceptor.
式中、Ａはフェノール性ＯＨ基を有するカップラー残基
または２−メチルインドレニンＵ導体のカップラー残基
を示す。In the formula, A represents a coupler residue having a phenolic OH group or a coupler residue of the 2-methylindolenine U conductor.
さらに詳しくは、上記一般式（１）におけるカップラー
残基Ａは、例えば下記一般式（２）〜（８）のいずれか
で示される基である。More specifically, the coupler residue A in the above general formula (1) is, for example, a group represented by any of the following general formulas (2) to (8).
一般式
ＮＵ
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、ヘテロ環基
、イミノ基あるいはＲ，、Ｒ２の結合する窒素原子と一
緒に環状アミ７基を示し。General formula NU In the formula, R1 and R2 are a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group, an aryl group, a heterocyclic group, an imino group, or a cyclic group together with the nitrogen atom to which R, R2 is bonded. Shows 7 amino groups.
又はベンゼン環と縮合して多環芳香環あるいはへテロ環
を形成する残基を示し、Ｒ３およびＲ４は置換基を有し
てもよいアルキル基、アラルキル基あるいはアリール基
を示し、Ｙは芳香族炭化水素の２価の基あるいは窒素原
子と共にヘテロ環を形成する２価の基を示し、Ｒ５およ
びＲ６は水素原子、アルキル基、アルコキシ基、ハロゲ
ン原子、シアノ基あるいはニトロ基を示す。or a residue that forms a polycyclic aromatic ring or a heterocycle by condensing with a benzene ring, R3 and R4 represent an alkyl group, an aralkyl group, or an aryl group that may have a substituent, and Y is an aromatic group. It represents a divalent hydrocarbon group or a divalent group forming a heterocycle with a nitrogen atom, and R5 and R6 represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a cyano group, or a nitro group.
上記定義において、アルキル基、アラルキル基、アリー
ル基、アルコキシ基およびヘテロ環基の例としては、ア
ルキル基は例えばメチル、エチル、プロピルなど、アラ
ルキル基は例えばベンジル、ナフチルメチルなど、アリ
ール基は例えばフェニル、ジフェニル、ナフチル、アン
スリルなど、アルコキシ基は例えばメトキシ、エトキシ
、プロポキシなど、ヘテロ環基は例えばジベンゾフラン
、ベンズイミダシロン、ベンズチアゾール、チアゾール
、ピリジンなどが挙げられる。In the above definitions, examples of alkyl groups, aralkyl groups, aryl groups, alkoxy groups and heterocyclic groups include alkyl groups such as methyl, ethyl and propyl; aralkyl groups such as benzyl and naphthylmethyl; and aryl groups such as phenyl. , diphenyl, naphthyl, anthryl, etc.; examples of alkoxy groups include methoxy, ethoxy, propoxy, etc.; examples of heterocyclic groups include dibenzofuran, benzimidacylon, benzthiazole, thiazole, pyridine, etc.
上記アルキル基、アラルキル基、アリール基、アルコキ
シ基、ヘテロ環基およびイミノ基における置換基として
は例えばハロゲン原子、ニトロ基、シアノ基、置換アミ
ノ基（例えばジメチルアミノ、ジフェニルアミノ、ジベ
ンジルアミノなど）、アルキル基、アルコキシ基などが
挙げられる。Substituents for the above alkyl groups, aralkyl groups, aryl groups, alkoxy groups, heterocyclic groups and imino groups include, for example, halogen atoms, nitro groups, cyano groups, substituted amino groups (e.g. dimethylamino, diphenylamino, dibenzylamino, etc.) , an alkyl group, an alkoxy group, and the like.
またＸのベンゼン環と共に多環芳香族環あるいはへテロ
環を形成する残基としては例えばナフタレン環、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、ベンゾナフトフラン環、ジフェニレン
サルファイド環などが挙げられる。Examples of residues that form a polycyclic aromatic ring or heterocycle with the benzene ring of Can be mentioned.
またＹの２価の基としては例えばフェニレン基ナフチレ
ン基などが挙げられる。Further, examples of the divalent group of Y include phenylene group and naphthylene group.
以下、前記一般式（１）で示されるトリスアゾ顔料の代
表例を列挙する。Representative examples of the trisazo pigment represented by the general formula (1) are listed below.
なお、下記基本型においてＡのみが相違するので例示は
Ａのみを示すこととする。Note that in the following basic types, only A is different, so only A is shown as an example.
ＮＵ
これらのトリスアゾ顔料は、１種または２種以上を組合
せて用いることができる。NU These trisazo pigments can be used alone or in combination of two or more.
これらのトリスアゾ顔料は、
例えば
で示されるトリアミンを常法によりヘキサジ化して、こ
れに、対応する前記一般式（２）〜（８）で示される基
を有するカップラーをアルカリの存在下にカップリング
するか、または上記のトリアミンのへキサゾニウム塩を
ホウフッ化塩あるいは塩化亜鉛複塩などの形で一旦単離
した後、適当な溶媒例えば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溶媒中でアルカリの存
在下に対応する前記一般式（２）〜（８）で示される基
を有するカップラーとカップリングすることにより容易
に製造することができる。These trisazo pigments can be obtained by, for example, hexaziding the triamine represented by the above in a conventional manner, and coupling thereto a coupler having a group represented by the corresponding general formulas (2) to (8) above in the presence of an alkali. Alternatively, once the hexazonium salt of the above triamine is isolated in the form of a borofluoride salt or a zinc chloride double salt, it is isolated in the presence of an alkali in a suitable solvent such as N,N-dimethylformamide or dimethyl sulfoxide. It can be easily produced by coupling with a coupler having a group represented by the corresponding general formulas (2) to (8) below.
例示顔料（１）の合成例
５００ ｍ文ビーカーに水８ｏｆｆ１文、濃塩酸１６
．６ ｍ文（０，１９モル）および前記トリアミン７
．５ｇ（０，０１９モル）を入れ、氷水浴で冷却しなが
ら攪拌して液温を３°Ｃとした。Synthesis example of exemplified pigment (1) 500 m beaker, 8 off 1 m water, concentrated hydrochloric acid 16 m
．． 6 m (0,19 mol) and the triamine 7
．． 5 g (0,019 mol) was added thereto and stirred while cooling in an ice water bath to bring the liquid temperature to 3°C.
次に至硝酸ソーダ４．２ｇ（０，０６１モル）を水７ｆ
ｆ１文に溶した液を、液温を３〜ｌＯ°Ｃの範囲にコン
トロールしながら１０分間で滴下し、滴下終了後同温度
で更に３０分間攪拌した０反応液にカーボンを加え濾過
してヘキサジ化液を得た。Next, add 4.2g (0,061 mol) of sodium nitrate to 7f of water.
The solution dissolved in f1 was added dropwise over 10 minutes while controlling the temperature within the range of 3 to 10°C. After the dropwise addition was complete, the solution was stirred at the same temperature for an additional 30 minutes. Carbon was added to the reaction solution, filtered, and hexadiazole was added. A liquid solution was obtained.
次に２文ビーカーに水７００Ｉｌｉを入れ、苛性ソーダ
２１ｇ（０，５３モル）を溶解した後、ナフトールＡｓ
（３−ヒドロキシ−２−ナフトエ酸アニリド）１６．
２ｇ （０，０６１モル）を添加して溶解した。このカ
ップラー溶液を６°Ｃに冷却し、液温を６〜１０℃にコ
ントロールしながら上記のヘキサジ化液を３０分かけて
攪拌下、滴下してその後室温で２時間攪拌し、更に１晩
放置した。Next, put 700 Ili of water into a 2-liter beaker, dissolve 21 g (0.53 mol) of caustic soda, and then add naphthol As
(3-Hydroxy-2-naphthoic acid anilide) 16.
2g (0,061 mol) was added and dissolved. This coupler solution was cooled to 6°C, and while controlling the liquid temperature at 6 to 10°C, the above hexazidation solution was added dropwise with stirring over 30 minutes, then stirred at room temperature for 2 hours, and then left overnight. did.
反応液を濾過後水洗し、粗製顔料１９．８ｇを得た。The reaction solution was filtered and washed with water to obtain 19.8 g of a crude pigment.
次に４００ＩＩ１文のＮ、Ｎ−ジメチルホルムアミドで
熱癌過を５回繰り返した。その後、減圧熱乾燥により精
製顔料１８．６ｇを得た。Next, heat treatment was repeated five times with N,N-dimethylformamide of 400II. Thereafter, 18.6 g of purified pigment was obtained by heat drying under reduced pressure.
収率は８０．６％であった。The yield was 80.6%.
元素分析：
計算値（％） 実験値（％）
Ｃ７５，１１７５，００
Ｈ４，１５４，１１
Ｎ １１．５３ １１．５１
前記一般式（１）で示されるトリスアゾ顔料を含有する
被膜は、光導電性を示し、従って電子写真感光体の感光
層に用いることができる。Elemental analysis: Calculated value (%) Experimental value (%) C75,1175,00 H4,154,11 N 11.53 11.51 The film containing the trisazo pigment represented by the general formula (1) has photoconductivity. Therefore, it can be used in the photosensitive layer of an electrophotographic photoreceptor.
電子写真感光体は、導電性基体上に前記トリスアゾ顔料
を真空蒸着法により被膜形成するか、あるいは適当なバ
インダーに分散含有させて被膜形成することによって作
成される。The electrophotographic photoreceptor is prepared by forming a film of the trisazo pigment on a conductive substrate by vacuum evaporation, or by dispersing and containing the trisazo pigment in a suitable binder.
本発明の好ましい実施態様では感光層を電荷発生層と電
荷輸送層に機能分離した電子写真感光体における電荷発
生層として上記の光導電性被１１ ヲ使用することがで
きる。In a preferred embodiment of the present invention, the photoconductive coating 11 described above can be used as a charge generation layer in an electrophotographic photoreceptor in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer.
電荷発生層は十分な吸光分を得るためできる限り多くの
量の光導電物質を含有し、かつ発生した電荷キャリアの
飛程を短くするため被膜、例えば５ｐＬｍ以下、好まし
くは０．０１〜ｌルｍの膜厚の薄膜とすることが望まし
い。The charge generation layer contains as much photoconductive material as possible in order to obtain sufficient light absorption, and is coated with a coating, for example, 5 pLm or less, preferably 0.01 to 1 Lm, to shorten the range of the generated charge carriers. It is desirable to form a thin film with a thickness of m.
このことは入射光線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. It is caused by something.
電荷発生層は、例えば前記トリス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、また真空蒸着装置により蒸着膜を形成する
ことによって得ることができる。電荷発生層は２種類以
上の電荷発生層を積層して用いることもできる。The charge generation layer can be formed, for example, by dispersing the trisazo pigment in a suitable binder and coating it on a substrate, or by forming a vapor deposited film using a vacuum vapor deposition apparatus. The charge generation layer can also be used by laminating two or more types of charge generation layers.
電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。好ましく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、ポリエステノに、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。電荷発生層中に含有する樹脂は、８
０重量％以下、好ましくは４０重量％以下が適している
。The binder that can be used to form the charge generating layer by coating can be selected from a wide variety of insulating resins, and can also be selected from organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene, and polyvinylpyrene. Preferably polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.),
Polycarbonate, polyester, phenoxy resin,
polyvinyl acetate, acrylic resin, polyacrylamide,
polyamide, polyvinylpyridine, cellulose resin,
Examples include insulating resins such as polyurethane, epoxy resin, casein, polyvinyl alcohol, and polyvinylpyrrolidone. The resin contained in the charge generation layer is 8
A content of 0% by weight or less, preferably 40% by weight or less is suitable.
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、
イソ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 isopropanol, 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, aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, and trichloroethylene, or benzene, toluene, xylene, ligroin, monochlorobenzene, dichlorobenzene, etc. aromatic hydrocarbons and the like 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、
マイヤーパーコーティング法、ブレードコーチインク法
、ローラーコーチインク法、カーテンコーティング法な
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,
This can be carried out using a coating method such as a Mayer-Par coating method, a blade coach ink method, a roller coach ink method, or a curtain coating method.
乾燥は、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℃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。Drying is preferably carried out by drying to the touch at room temperature and then heating. Drying by heating is performed at a temperature of 30 to 200°C for 5 minutes to
It can be carried out stationary or under blown air for a time in the range of 2 hours.
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。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. At this time, this charge transport layer may be laminated on or under the charge generation layer.
電荷輸送物質として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クロルアニル、ブロモ
アニル、テトラシアノエチレン。Charge transporting substances include electron transporting substances and hole transporting substances, and electron transporting substances include chloranil, bromoanil, and tetracyanoethylene.
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−テトラニトロ−
９−フルオレノン、２．．４．７−ドリニトロー９−ジ
シアノ、メチレンフルオレノン、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。Tetracyanoquinodimethane, 2°, 4,7-dolinitro-9-fluorenone, 2,4,5,7-tetranitro-
9-fluorenone, 2. ．． Electron-withdrawing substances such as 4,7-dolinitro-9-dicyano, methylenefluorenone, 2,4,5,7-titranitroxanthone, and 2,4,8-trinidrothioxanthone, and polymerization of these electron-withdrawing substances There are things.
正孔輸送性物質としてはピレン、Ｎ−エチルカルバゾー
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、Ｎ、Ｎ−−ジ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、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、Ｎ、Ｎ−ジフェニルヒドラジノ−３−メチリデン
−１０−二チルフェノキサジン、Ｐ−ジエチルアミノベ
ンズアルデヒド−Ｎ、Ｎ−ジフェニルヒドラゾン、ｐ−
ジエチルアミノベンズアルデヒド−Ｎ−α−ナフチル−
Ｎ−フェニルヒドラゾン、ｐ−ピロリジノベンズアルデ
ヒド−Ｎ、Ｎ−ジフェニルヒドラゾン、１，３．３−ト
リメチルインドレニン−ω−アルデヒド−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
−メチルベンズチアゾリノン−２−ヒドラゾンなどのヒ
ドラゾン類、２．５−ビス（ｐ−ジエチルアミノフェニ
ル）−１，３，４−オキサジアゾール、１−［キノリル
（２）−２−（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−［６−
メドキシーピリジル（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−［レビジル（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、１−フェニル−
３−（α−ベンジル−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、スピ
ロピラゾリンなどのピラゾリン類、２−（ｐ−ジエチル
アミノスチリル）−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−エチレン、アニル）−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、エチル力ルバゾールーホルムアルデヒト樹脂など
がある。Examples of hole-transporting substances include pyrene, N-ethylcarbazole, N-isopropylcarbazole, and N-methyl-N-
Phenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-10-ditylphenothiazine, N , N-diphenylhydrazino-3-methylidene-10-ditylphenoxazine, P-diethylaminobenzaldehyde-N,N-diphenylhydrazone, p-
Diethylaminobenzaldehyde-N-α-naphthyl-
N-phenylhydrazone, p-pyrrolidinobenzaldehyde-N, N-diphenylhydrazone, 1,3.3-trimethylindolenine-ω-aldehyde-N, N-diphenylhydrazone, P-diethylbenzaldehyde-3
-Hydrazones such as methylbenzthiazolinone-2-hydrazone, 2,5-bis(p-diethylaminophenyl)-1,3,4-oxadiazole, 1-[quinolyl(2)-2-(p- diethylaminostyryl)-5-(
p-diethylaminophenyl)pyrazoline, 1-[6-
Medoxypyridyl(2)]-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[Levidyl(2)]-3-(p-diethylaminostyryl)-5-(p- diethylaminophenyl)pyrazoline, 1-[pyridyl(2)]-3-(α
-methyl-p-diethylaminostyryl)-5-(p-
diethylaminophenyl)pyrazoline, 1-phenyl-
3-(α-benzyl-p-diethylaminostyryl)-
Pyrazolines such as 5-(p-diethylaminophenyl)pyrazoline and spiropyrazoline, 2-(p-diethylaminostyryl)-6-dinithylaminobenzoxazole, 2-(p-diethylaminophenyl)-4-(p
Oxazole compounds such as -dimethylaminophenyl)-5-(2-chlorophenyl)oxazole, 2-(
Thiazole compounds such as p-diethylaminostyryl)-6-dinithylaminobenzothiazole, bis(4-
Triarylmethane compounds such as diethylamino-2-ethylene, anyl)-phenylmethane, 1,1-bis(4-N,N-diethylamino-2-methylphenyl)
Hebutane, 1,1,2,2-tetrakis (4-N, N
-Polyarylalkanes such as dimethylamino-2-methylphenyl)ethane, triphenylamine, poly-
Examples include N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, poly-9-vinylphenylanthracene, pyrene-formaldehyde resin, and ethyl rubazole-formaldehyde resin.
これらの有機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 organic 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.
電荷輸送物質に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、ポ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、必要以上に膜厚を厚くすることができない、一般的
には５〜３０ＩＬｍであるが、好ましい範囲は８〜２０
７ｚｍである。塗工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。The charge transport layer has a limit in its ability to transport charge carriers, so it cannot be made thicker than necessary. Generally, the thickness is 5 to 30 ILm, but the preferred range is 8 to 20 ILm.
It is 7zm. When forming the charge transport layer by coating, an appropriate 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）、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とともにプラ
スチックの上に被覆した基体、導電性粒子をプラスチッ
クや紙に含浸した基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, ethylene chloride, etc.), conductive particles (e.g. carbon black, silver particles, etc.) coated on plastic with a suitable binder, conductive particles impregnated into plastic or paper, and plastics containing conductive polymers. Can be used.
導電層と感光層の中間に、バリヤー機能と接着機能をも
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、ゼラチン、酸
化アルミニウムなどによって形成できる。下引層の膜厚
は０．１〜５川ｍ、好ましくは０．５′〜３弘ｍが適当
である。A subbing layer having barrier and adhesive functions can also be provided between the conductive layer and the photosensitive layer. The subbing layer can be formed of casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer, polyamide (nylon 6, nylon 66, nylon 61O1 copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin, aluminum oxide, and the like. The appropriate thickness of the undercoat layer is 0.1 to 5 m, preferably 0.5' to 3 m.
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、帯電後露光すると帯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、その後表面に到
達して正電荷を中和し、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。このようにしてで
きた静電潜像を負荷電性のトナーで現像すれば可視像が
得られる。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。また感光体上の静電潜像を転写紙の絶
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。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 light band area, electrons generated in the charge generation layer are injected into the charge transport layer, and then reach the surface and neutralize the positive charge, causing a decrease in surface potential and creating an electrostatic contrast between it and the unexposed area. arise. A visible image is obtained by developing the electrostatic latent image thus formed with a negatively charged toner. This can be directly fixed, or the toner image can be transferred to paper or plastic film and then developed and fixed. Alternatively, a method may be used in which the electrostatic latent image on the photoreceptor is transferred onto an insulating layer of transfer paper, and then visualized and 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正孔が電荷
輸送層に注入され、その後表面に到達して負電荷を中和
し１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 made of a hole transport material, the surface of the charge transport layer must be negatively charged, and when exposed to light after charging, holes generated in the charge generation layer are injected into the charge transport layer in the exposed area. , then reaches the surface and neutralizes the negative charges, causing attenuation of the surface potential and creating an electrostatic contrast between the surface potential and the unexposed area. 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、前述の一般式（１）
で示されるトリスアゾ顔料である有機光導電体を前述の
電荷輸送物質とともに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。Furthermore, as another specific example of the present invention, the above general formula (1)
Examples include an electrophotographic photoreceptor in which an organic photoconductor which is a trisazo pigment represented by the above formula is contained in the same layer together with the charge transporting substance described above.
この際、電荷輸送物質としてポリ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化合物を用
いることができる。At this time, a charge transfer complex compound consisting of polyvinylcarbazole and trinitrofluorenone can be used as the charge transport substance.
この例の電子写真感光体は、前述の有機光導電体と電荷
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 above-described organic photoconductor and 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）で示されるトリスアゾ顔料から選ばれる少なく
とも１種類の顔料を含有し、必要に応じて光吸収の異な
る顔料を組合せて使用して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
）で示されるトリスアゾ顔料を２種類以上組合せたり、
または公知の染料顔料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。In any of the electrophotographic photoreceptors, the pigment used contains at least one type of pigment selected from trisazo pigments represented by the general formula (1), and if necessary, pigments with different light absorptions are used in combination. For the purpose of increasing the sensitivity of the body or obtaining a panchromatic photoreceptor, the general formula (1
) A combination of two or more types of trisazo pigments,
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や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２２２ｍＪｌ）
をマイヤーバーで乾燥後の膜厚が１ 、０４ｍ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 222mJl)
was applied with a Mayer bar to a film thickness of 1.04 m after drying, and dried.
次に、前記例示顔料（７）の有機光導電体５ｇを、エタ
ノール９５＋ＪＬにブチラール樹脂（ブチラール化度６
３モル％）２ｇを溶解した液に加え、アトライターで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０．５ｇｍ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 the organic photoconductor of the exemplified pigment (7) was added to ethanol 95+JL with butyral resin (butyralization degree 6).
Add 2 g of 3 mol%) to the solution and add 2 g with an attritor
Spread out time. This dispersion was applied onto the previously formed casein layer using a Mayer bar so that the film thickness after drying was 0.5 gm, 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（
数平均分子量１０万）５ｇをベンゼン７０ＩＩ１文に溶
解し、これを電荷発生層の上に乾燥後の膜厚が１２７ｂ
ｍとなるようにマイヤーバーで塗布し、乾燥して電荷輸
送層を形成した。5g of hydrazone compound and polymethyl methacrylate (
Dissolve 5g of (number average molecular weight: 100,000) in 1 volume of benzene 70II, and apply this on the charge generation layer to a film thickness of 127b after drying.
The charge transport layer was coated with a Mayer bar and dried to form a charge transport layer.
こうして作成した電子写真感光体を静電複写紙試験装置
［５Ｐ−４２８（ターンテーブル）］を用いてスタチッ
ク方式で一５ＫＶでコロナ帯電し、暗所で１秒間保持し
た後、照度２文ＵＸで露光し、帯電特性を調べた。The electrophotographic photoreceptor thus prepared was statically charged with corona at 15 KV using an electrostatic copying paper tester [5P-428 (turntable)], held in a dark place for 1 second, and then set at an illuminance of 2 cm UX. It was exposed to light and its charging characteristics were examined.
帯電特性としては、表面電位（Ｖｏ ）と１秒間暗減衰
させた時の電位を１／２に減衰するに必要な露光量（Ｅ
１／２）を測定した。The charging characteristics include the surface potential (Vo) and the amount of light exposure (E) required to attenuate the potential by 1/2 when dark decaying for 1 second
1/2) was measured.
さらに、繰り返し使用した時の明部電位と暗部電位の変
動を測定するために、上記作成した電子写真感光体を−
５，８ＫＶのコロナ帯電器、露光量５ｆＬｕｘ、ｓｅｅ
を宥する露光光学系、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
い転写紙上に画像が得られる構成になっている。Furthermore, in order to measure the fluctuations in bright area potential and dark area potential when repeatedly used, the electrophotographic photoreceptor prepared above was used.
5.8KV corona charger, exposure amount 5fLux, see
It was attached to the cylinder of an electrophotographic copying machine equipped with an exposure optical system, a developing device, 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、初期の明部電位（ＶＬ ）と暗部
電位（ＶＤ ）および５．０００回使用した後の明部電
位（ＶＬ ）と暗部電位（Ｖｏ）を測定した。この結果
を示す。Using this copying machine, the initial bright area potential (VL) and dark area potential (VD) and the bright area potential (VL) and dark area potential (Vo) after 5,000 uses were measured. The results are shown below.
ｖｏｗ−５９５Ｖ。vow-595V.
Ｅｌ／２ ： ２．４Ｊｌｕｘ、ｓｅ、ｃ初 期
５千枚耐久後
実施例２〜１５
実施例１で用いた例示顔料に代えて、下記の例示顔料を
用いた他は、全〈実施例１と同様の方法で電子写真感光
体を作成した。El/2: 2.4Jlux, se, c early
Examples 2 to 15 after 5,000-sheet durability Electrophotographic photoreceptors were prepared in the same manner as in Example 1, except that the following exemplified pigments were used in place of the exemplified pigments used in Example 1.
各感光体の帯電特性と耐久特性を実施例１と同様の方法
によって測定した。The charging characteristics and durability characteristics of each photoreceptor were measured in the same manner as in Example 1.
結果を示す。Show the results.
六 ７
４ （４） ｓ （６）
８ （１３，） ９ （１５
）２ ８０５ ２ 、４
３ ６１０ ２．６
４ ６００ ２ 、５
５ ６２０ ２ 、８
６ ６２０ ２ 、７
７ ６１０ ２．６８
６１５ ２．８９ ６１０
２．６１ ０ ６００
２ 、 ３１１ ６０５
２．４１２ ８２０ ２．９１
３ ６０５ ２．８１４
６１０ ２．９１５ ６
００ ２．５４ ｆ５０５ ３０
．８２０ ５５１０ ６．２０ ４
０ ８４５ ７５実施例１６
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−２，２−７’ロバンカーボネート（分
子量３０万）５ｇをテトラヒドロフラン７０ ｌｉに溶
解して調製した塗布液を乾燥後の塗工量が１０ｇ／ｍ２
となるように塗布し、乾燥した。6 7 4 (4) s (6)
8 (13,) 9 (15
)2 805 2 , 4 3 610 2.6 4 600 2 , 5 5 620 2 , 8 6 620 2 , 7 7 610 2.68
615 2.89 610
2.61 0 600
2, 311 605
2.412 820 2.91
3 605 2.814
610 2.915 6
00 2.54 f505 30
．． 820 5510 6.20 4
0 845 75 Example 16 On the charge generation layer prepared in Example 1, 5 g of 2,4,7-dolinitro-9-fluorenone and poly-4,4-dioxydiphenyl-2,2-7'lovan carbonate ( The coating amount after drying a coating solution prepared by dissolving 5 g of molecular weight 300,000 in 70 li of tetrahydrofuran was 10 g/m2.
It was applied 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
法で帯電特性を測定した。このとき帯電は十とした。結
果を示す。The charging characteristics of the electrophotographic photoreceptor thus prepared were measured in the same manner as in Example 1. At this time, the charge was set to 10. Show the results.
ＶＱ ：＋５８０Ｖ、
Ｅｌ／２：４．８Ｊｌｕｘ、ｓｅｃ、
初 期
ＶＤ：＋５７５Ｖ、ＶＬ：＋６０Ｖ
５千枚耐久後
ＶＤ ：＋６００Ｖ、ＶＬ ：＋９０Ｖ実施例１７
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１．ＯＩＬｍのポリビニルアルコールの被
膜を形成した。VQ: +580V, El/2: 4.8Jlux, sec, initial VD: +575V, VL: +60V VD after 5,000 sheets durability: +600V, VL: +90V Example 17 Film thickness on the aluminum surface of aluminum vapor-deposited polyethylene terephthalate film 1. A polyvinyl alcohol film of OILm was formed.
次に、実施例１で用いた例示顔料（７）の分散液を先に
形成したポリビニルアルコール層上に、乾燥後の膜厚が
０．５１Ｌｍ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 exemplary pigment (7) used in Example 1 was applied onto the previously formed polyvinyl alcohol layer using a Mayer bar so that the film thickness after drying was 0.51 Lm, and dried. A charge generation layer was formed.
次いで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）
ピラゾリンを５ｇとボリアリレート樹脂（ビスフェノー
ルＡとテレフタル酸−イソフタル酸の縮重合体）５ｇを
テトラヒドロフラン７０ｍ１に溶解した液を電荷発生層
の上に乾燥後の膜厚が１０ｐｍとなるように塗布し、乾
燥して電荷輸送層を形成した。Then 1-[pyridyl(2)]-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)
A solution prepared by dissolving 5 g of pyrazoline and 5 g of polyarylate resin (condensation polymer of bisphenol A and terephthalic acid-isophthalic acid) in 70 ml of tetrahydrofuran was applied onto the charge generation layer so that the film thickness after drying was 10 pm. It was dried to form a charge transport layer.
こうして作成した電子写真感光体について帯電特性およ
び耐久特性を実施例１と同様の方法で測定した。結果を
示す。The charging characteristics and durability characteristics of the electrophotographic photoreceptor thus prepared were measured in the same manner as in Example 1. Show the results.
ｖｏニー６１０Ｖ、
Ｅｌ／２ ： ２．６ｕｕｘ、ｓｅｃ、初 期
Ｖｏ ニー６１５Ｖ、 ｖＬ ニー４０Ｖ５千枚耐久後
Ｖ ｏ ： −６２０Ｖ 、 Ｖ Ｌ ： −６
０Ｖ実施例１８
厚さ１１００ｐＬ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１．ｏｐｍの下引層を形
成した。Vony 610V, El/2: 2.6uux, sec, initial Vo knee 615V, vL knee 40V after 5,000 sheets durability Vo: -620V, VL: -6
0V Example 18 An ammonia aqueous solution of casein was coated on an aluminum plate with a thickness of 1100 pL and dried to a film thickness of 1. A subbing layer of opm was formed.
次に、２，４．７−）リニトロー９−フルオレノン５ｇ
とポリ−Ｎ−ビニルカルバゾール（数平均分子量３０万
）５ｇをテトラヒドロフラン７０ｍ文に溶解して電荷移
動錯化合物を調製した。Next, 5 g of 2,4.7-)linitro-9-fluorenone
A charge transfer complex compound was prepared by dissolving 5 g of poly-N-vinylcarbazole (number average molecular weight: 300,000) in 70 mL of tetrahydrofuran.
この電荷移動錯化合物と例示顔料（１９）の光導電体１
ｇを、ポリエステル樹脂５ｇをテトラヒドロフラン７０
ｍＪｌに溶解した液に加え１分散した。この分散液を下
引層の上に乾燥後の膜厚が１２ｐｍとなるように塗布し
、乾燥した。Photoconductor 1 of this charge transfer complex compound and exemplary pigment (19)
g, 5 g of polyester resin and 70 g of tetrahydrofuran.
It was added to the solution dissolved in mJl and dispersed. This dispersion liquid was applied onto the undercoat layer so that the film thickness after drying was 12 pm, 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
と同様の方法で測定した。Example 1 Charging characteristics of the electrophotographic photoreceptor thus prepared
It was measured in the same manner as.
但し、帯電極性は十とした。結果を示す。However, the charging polarity was set to 10. Show the results.
ｖｏ ：＋５８０Ｖ、
Ｅ １／２ ： ５ 、目、ｕｘ、ｓｅｃ、［発明の効
果］
本発明の電子写真感光体は特定構造のトリスアゾ顔料を
感光層に用いることにより、当該トリスアゾ顔料を含む
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ないし双方が良くなることが推
定され、高感度で耐久使用時における電位安定性に優れ
た顕著な効果を奏する。vo: +580V, E 1/2: 5, eyes, ux, sec, [Effects of the invention] The electrophotographic photoreceptor of the present invention uses a trisazo pigment with a specific structure in the photosensitive layer, so that the photosensitive layer containing the trisazo pigment It is estimated that either one or both of the internal carrier generation efficiency and the carrier transport efficiency are improved, and the remarkable effect of high sensitivity and excellent potential stability during long-term use is achieved.
Claims (3)
１）で示されるトリスアゾ顔料の少なくとも一種を光導
電体として含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、Ａはフェノール性ＯＨ基を有するカップラー残基
または２−メチルインドレニン誘導体のカップラー残基
を示す。(1) The following general formula (
An electrophotographic photoreceptor comprising at least one of the trisazo pigments shown in 1) as a photoconductor. General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (1) In the formula, A represents a coupler residue having a phenolic OH group or a coupler residue of a 2-methylindolenine derivative.
般式（２）〜（８）で示される基から選ばれるカップラ
ー残基である特許請求の範囲第１項記載の電子写真感光
体。 一般式 ▲数式、化学式、表等があります▼（２） ▲数式、化学式、表等があります▼（３）▲数式、化学
式、表等があります▼（４） ▲数式、化学式、表等があります▼（５）▲数式、化学
式、表等があります▼（６） ▲数式、化学式、表等があります▼（７） ▲数式、化学式、表等があります▼（８） 式中、Ｒ＿１およびＲ＿２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、ヘテロ
環基、イミノ基あるいはＲ＿１、Ｒ＿２の結合する窒素
原子と一緒に環状アミノ基を示し、Ｘはベンゼン環と縮
合して多環芳香環あるいはヘテロ環を形成する残基を示
し、Ｒ＿３およびＲ＿４は置換基を有してもよいアルキ
ル基、アラルキル基あるいはアリール基を示し、Ｙは芳
香族炭化水素の２価の基あるいは窒素原子と共にヘテロ
環を形成する２価の基を示し、Ｒ＿５およびＲ＿６は水
素原子、アルキル基、アルコキシ基、ハロゲン原子、シ
アノ基あるいはニトロ基を示す。(2) The electrophotographic photoreceptor according to claim 1, wherein the coupler residue A in the general formula (1) is a coupler residue selected from the groups represented by the following general formulas (2) to (8). General formulas ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (2) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (3) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (4) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼(5) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (6) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (7) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (8) In the formula, R_1 and R_2 are A hydrogen atom, an alkyl group that may have a substituent, an aralkyl group, an aryl group, a heterocyclic group, an imino group, or a cyclic amino group together with the nitrogen atom to which R_1 and R_2 are bonded, and X is fused with a benzene ring. represents a residue forming a polycyclic aromatic ring or a heterocycle, R_3 and R_4 represent an alkyl group, an aralkyl group, or an aryl group that may have a substituent, and Y represents a divalent aromatic hydrocarbon. It represents a divalent group that forms a heterocycle with a group or a nitrogen atom, and R_5 and R_6 represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a cyano group, or a nitro group.
積層型感光層であり、該電荷発生層に前記一般式（１）
で示されるトリスアゾ顔料を含有する特許請求の範囲第
１項記載の電子写真感光体。(3) The photosensitive layer is a laminated photosensitive layer consisting of a charge generation layer and a charge transport layer, and the charge generation layer has the general formula (1).
The electrophotographic photoreceptor according to claim 1, which contains a trisazo pigment represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1133187A JPS63180957A (en) | 1987-01-22 | 1987-01-22 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1133187A JPS63180957A (en) | 1987-01-22 | 1987-01-22 | Electrophotographic sensitive body |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63180957A true JPS63180957A (en) | 1988-07-26 |
Family
ID=11775048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1133187A Pending JPS63180957A (en) | 1987-01-22 | 1987-01-22 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63180957A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03128958U (en) * | 1990-04-06 | 1991-12-25 | ||
| US8399899B2 (en) | 2009-07-01 | 2013-03-19 | Sharp Kabushiki Kaisha | Light emitting device |
| US8421094B2 (en) | 2010-01-22 | 2013-04-16 | Sharp Kabushiki Kaisha | Light emitting device |
| US8575630B2 (en) | 2009-03-03 | 2013-11-05 | Sharp Kabushiki Kaisha | Light emitting device, light emitting device unit, and method for fabricating light emitting device |
| US9607970B2 (en) | 2009-11-13 | 2017-03-28 | Sharp Kabushiki Kaisha | Light-emitting device having a plurality of concentric light transmitting areas |
-
1987
- 1987-01-22 JP JP1133187A patent/JPS63180957A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03128958U (en) * | 1990-04-06 | 1991-12-25 | ||
| US8575630B2 (en) | 2009-03-03 | 2013-11-05 | Sharp Kabushiki Kaisha | Light emitting device, light emitting device unit, and method for fabricating light emitting device |
| US8399899B2 (en) | 2009-07-01 | 2013-03-19 | Sharp Kabushiki Kaisha | Light emitting device |
| US9607970B2 (en) | 2009-11-13 | 2017-03-28 | Sharp Kabushiki Kaisha | Light-emitting device having a plurality of concentric light transmitting areas |
| US8421094B2 (en) | 2010-01-22 | 2013-04-16 | Sharp Kabushiki Kaisha | Light emitting device |
| US8723195B2 (en) | 2010-01-22 | 2014-05-13 | Sharp Kabushiki Kaisha | Light emitting device with plurality of LED chips and/or electrode wiring pattern |
| US9093357B2 (en) | 2010-01-22 | 2015-07-28 | Sharp Kabushiki Kaisha | Light emitting device |
| US9312304B2 (en) | 2010-01-22 | 2016-04-12 | Sharp Kabushiki Kaisha | LED illuminating device comprising light emitting device including LED chips on single substrate |
| US9425236B2 (en) | 2010-01-22 | 2016-08-23 | Sharp Kabushiki Kaisha | Light emitting device |
| US9679942B2 (en) | 2010-01-22 | 2017-06-13 | Sharp Kabushiki Kaisha | Light emitting device |
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| JPS63180961A (en) | Electrophotographic sensitive body | |
| JPS63174048A (en) | Electrophotographic sensitive body | |
| JPS63180958A (en) | Electrophotographic sensitive body | |
| JPS63174049A (en) | Electrophotographic sensitive body | |
| JPS6364050A (en) | Electrophotographic sensitive body | |
| JPS63175863A (en) | Electrophotographic sensitive body | |
| JPS63174051A (en) | Electrophotographic sensitive body | |
| JPS63180959A (en) | Electrophotographic sensitive body | |
| JPS63175865A (en) | Electrophotographic sensitive body | |
| JPS63174052A (en) | Electrophotographic sensitive body | |
| JPS6364051A (en) | Electrophotographic sensitive body | |
| JPS63175861A (en) | Electrophotographic sensitive body | |
| JPS61260251A (en) | Electrophotographic sensitive body | |
| JPS63174050A (en) | Electrophotographic sensitive body | |
| JPH0232359A (en) | Electrophotographic sensitive body |