JPH0369962A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0369962A JPH0369962A JP20485389A JP20485389A JPH0369962A JP H0369962 A JPH0369962 A JP H0369962A JP 20485389 A JP20485389 A JP 20485389A JP 20485389 A JP20485389 A JP 20485389A JP H0369962 A JPH0369962 A JP H0369962A
- Authority
- JP
- Japan
- Prior art keywords
- photoreceptor
- group
- charge
- formula
- photosensitive 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.)
- Granted
Links
- -1 disazo compound Chemical class 0.000 claims abstract description 22
- 125000005647 linker group Chemical group 0.000 claims abstract description 6
- 108091008695 photoreceptors Proteins 0.000 claims description 57
- 239000000126 substance Substances 0.000 claims description 22
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 27
- 230000035945 sensitivity Effects 0.000 abstract description 10
- 239000011230 binding agent Substances 0.000 abstract description 7
- 150000004945 aromatic hydrocarbons Chemical group 0.000 abstract description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 6
- 229920005989 resin Polymers 0.000 abstract description 6
- 239000011347 resin Substances 0.000 abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 abstract description 4
- 230000006866 deterioration Effects 0.000 abstract description 3
- 125000000962 organic group Chemical group 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 239000000758 substrate Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000049 pigment Substances 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 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
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 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
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 239000001294 propane 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
- 239000011669 selenium Substances 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZXBSSAFKXWFUMF-UHFFFAOYSA-N 1,2,3-trinitrofluoren-9-one Chemical compound C12=CC=CC=C2C(=O)C2=C1C=C([N+](=O)[O-])C([N+]([O-])=O)=C2[N+]([O-])=O ZXBSSAFKXWFUMF-UHFFFAOYSA-N 0.000 description 1
- NGQSLSMAEVWNPU-UHFFFAOYSA-N 1,2-bis(2-phenylethenyl)benzene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1C=CC1=CC=CC=C1 NGQSLSMAEVWNPU-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
- AOLUMCPVEUKWBX-UHFFFAOYSA-N 1-[2-[2-[2-(2,4-dimethoxyphenyl)ethenyl]phenyl]ethenyl]-2,4-dimethoxybenzene Chemical compound COC1=CC(OC)=CC=C1C=CC1=CC=CC=C1C=CC1=CC=C(OC)C=C1OC AOLUMCPVEUKWBX-UHFFFAOYSA-N 0.000 description 1
- LFKNYYQRWMMFSM-UHFFFAOYSA-N 1-ethyl-9h-carbazole;formaldehyde Chemical compound O=C.N1C2=CC=CC=C2C2=C1C(CC)=CC=C2 LFKNYYQRWMMFSM-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 1
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- CLQYLLIGYDFCGY-UHFFFAOYSA-N 4-(2-anthracen-9-ylethenyl)-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=C(C=CC=C2)C2=CC2=CC=CC=C12 CLQYLLIGYDFCGY-UHFFFAOYSA-N 0.000 description 1
- PLVXCTLGYWKUAY-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethenyl)-n,n-diphenylaniline Chemical compound C=1C=CC2=CC=CC=C2C=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 PLVXCTLGYWKUAY-UHFFFAOYSA-N 0.000 description 1
- GAYAMEKFIBYRJW-UHFFFAOYSA-N 4-(fluoren-9-ylidenemethyl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=C1C2=CC=CC=C2C2=CC=CC=C21 GAYAMEKFIBYRJW-UHFFFAOYSA-N 0.000 description 1
- YGBCLRRWZQSURU-UHFFFAOYSA-N 4-[(diphenylhydrazinylidene)methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 YGBCLRRWZQSURU-UHFFFAOYSA-N 0.000 description 1
- VWEQSBRKYZRWPQ-UHFFFAOYSA-N 4-[2-(10-bromoanthracen-9-yl)ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=C(C=CC=C2)C2=C(Br)C2=CC=CC=C12 VWEQSBRKYZRWPQ-UHFFFAOYSA-N 0.000 description 1
- JJQOKUCYWIGCIN-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)-2-ethenyl-1,3-oxazol-5-yl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)N=C(C=C)O1 JJQOKUCYWIGCIN-UHFFFAOYSA-N 0.000 description 1
- AEEHOVNCLFTKTO-UHFFFAOYSA-N 4-[[benzyl(phenyl)hydrazinylidene]methyl]-n,n-diphenylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)N=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 AEEHOVNCLFTKTO-UHFFFAOYSA-N 0.000 description 1
- SBMCZDLOXDWNIN-UHFFFAOYSA-N 4-[bis[4-(diethylamino)phenyl]methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)C1=CC=C(N(CC)CC)C=C1 SBMCZDLOXDWNIN-UHFFFAOYSA-N 0.000 description 1
- MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-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
- FVGPNZKTTWPLOC-UHFFFAOYSA-N 9-ethyl-3-(2-phenylethenyl)carbazole Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=CC1=CC=CC=C1 FVGPNZKTTWPLOC-UHFFFAOYSA-N 0.000 description 1
- BODPVHGDJHVWAW-UHFFFAOYSA-N 9-ethyl-3-[2-(4-methoxyphenyl)ethenyl]carbazole Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=CC1=CC=C(OC)C=C1 BODPVHGDJHVWAW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- MKYQPGPNVYRMHI-UHFFFAOYSA-N Triphenylethylene Chemical compound C=1C=CC=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 MKYQPGPNVYRMHI-UHFFFAOYSA-N 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- MUBKMWFYVHYZAI-UHFFFAOYSA-N [Al].[Cu].[Zn] Chemical compound [Al].[Cu].[Zn] MUBKMWFYVHYZAI-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 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 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- OHUWRYQKKWKGKG-UHFFFAOYSA-N formaldehyde;pyrene Chemical compound O=C.C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 OHUWRYQKKWKGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- BVTXDOPTUCCGGU-UHFFFAOYSA-N n,n-diethyl-4-(2-naphthalen-1-ylethenyl)aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC=CC2=CC=CC=C12 BVTXDOPTUCCGGU-UHFFFAOYSA-N 0.000 description 1
- FBZZYZMCLSMELP-UHFFFAOYSA-N n,n-diethyl-4-(2-phenylethenyl)aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC=CC=C1 FBZZYZMCLSMELP-UHFFFAOYSA-N 0.000 description 1
- GAZKGHIEJKXNCQ-UHFFFAOYSA-N n,n-diethyl-4-(4-phenyl-1,3-oxazol-2-yl)aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NC(C=2C=CC=CC=2)=CO1 GAZKGHIEJKXNCQ-UHFFFAOYSA-N 0.000 description 1
- YRFZPZPDMPVXPZ-UHFFFAOYSA-N n,n-diethyl-4-[5-(9-ethylcarbazol-3-yl)-1,3,4-oxadiazol-2-yl]aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NN=C(C=2C=C3C4=CC=CC=C4N(CC)C3=CC=2)O1 YRFZPZPDMPVXPZ-UHFFFAOYSA-N 0.000 description 1
- UAVOVDWXWRXKPS-UHFFFAOYSA-N n-[(4-methoxyphenyl)methylideneamino]-n-methylaniline Chemical compound C1=CC(OC)=CC=C1C=NN(C)C1=CC=CC=C1 UAVOVDWXWRXKPS-UHFFFAOYSA-N 0.000 description 1
- QYXUHIZLHNDFJT-UHFFFAOYSA-N n-[(9-ethylcarbazol-3-yl)methylideneamino]-n-methylaniline Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=NN(C)C1=CC=CC=C1 QYXUHIZLHNDFJT-UHFFFAOYSA-N 0.000 description 1
- CEAPHJPESODIQL-UHFFFAOYSA-N n-[(9-ethylcarbazol-3-yl)methylideneamino]-n-phenylaniline Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 CEAPHJPESODIQL-UHFFFAOYSA-N 0.000 description 1
- ZQKFNYHHBMBPHU-UHFFFAOYSA-N n-benzyl-n-[(2,4-dimethoxyphenyl)methylideneamino]aniline Chemical compound COC1=CC(OC)=CC=C1C=NN(C=1C=CC=CC=1)CC1=CC=CC=C1 ZQKFNYHHBMBPHU-UHFFFAOYSA-N 0.000 description 1
- RPHJRJPXKZMFFQ-UHFFFAOYSA-N n-benzyl-n-[(9-ethylcarbazol-3-yl)methylideneamino]aniline Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=NN(C=1C=CC=CC=1)CC1=CC=CC=C1 RPHJRJPXKZMFFQ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 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、電子写真用感光体に関するものである。さら
に詳しくは、導電性支持体上の感光層に電荷発生物質と
して特定のジスアゾ化合物を含有させてなる電子写真用
感光体に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a photoreceptor for electrophotography. More specifically, the present invention relates to an electrophotographic photoreceptor in which a photosensitive layer on a conductive support contains a specific disazo compound as a charge generating substance.
従来、電子写真用感光体の感光材料としてセレン、硫化
カドミウム、酸化亜鉛などの無機系感光材料が広く使用
されてきた。しかしながら、これらの感光材料を用いた
感光体は、感度、光安定性、耐湿性、耐久性などの電子
写真用感光体としての要求性能を十分に満足するもので
はなかった。例えば、セレン系材料を用いた感光体は優
れた感度を有するが、熱または汚れの付着などにより結
晶化し、感光体の特性が劣化しやすい、また、真空蒸着
により製造するのでコストが高く、また可撓性がないた
め、ベルト状に加工するのが難しいなどの多くの欠点も
同時に有している。硫化カド≧ウム系材料を用いた感光
体では、耐湿性及び耐久性、また硫化亜鉛を用いた感光
体では耐久性に問題があった。Conventionally, inorganic photosensitive materials such as selenium, cadmium sulfide, and zinc oxide have been widely used as photosensitive materials for electrophotographic photoreceptors. However, photoreceptors using these photosensitive materials do not fully satisfy the performance requirements for electrophotographic photoreceptors, such as sensitivity, photostability, moisture resistance, and durability. For example, photoreceptors using selenium-based materials have excellent sensitivity, but they tend to crystallize due to heat or dirt adhesion, resulting in deterioration of photoreceptor characteristics.Also, they are manufactured by vacuum evaporation, which is expensive, and It also has many drawbacks, such as being difficult to process into a belt because of its lack of flexibility. Photoreceptors using cad≧ium sulfide materials have problems in moisture resistance and durability, and photoreceptors using zinc sulfide have problems in durability.
これら無機系感光材料を用いた感光体の欠点を克服する
ために、有機系感光材料を使用した感光体が種々検討さ
れてきた。In order to overcome the drawbacks of photoreceptors using inorganic photosensitive materials, various photoreceptors using organic photosensitive materials have been studied.
例えば、一部実用化された有機系感光材料として、２，
４．Ｔ−トリニトロ−９−フルオレノンとポリＮ−ビニ
ルカルバゾールを組み合わせて使用したものが知られて
いる。しかし、これを用いた感光体は感度が低く、また
耐久性においても満足できるものではなかった。For example, as an organic photosensitive material that has been partially put into practical use, 2.
4. A combination of T-trinitro-9-fluorenone and polyN-vinylcarbazole is known. However, photoreceptors using this method had low sensitivity and were not satisfactory in terms of durability.
近年、上記のような欠点を改良するために開発された感
光体の中で、電荷発生機能と電荷輸送機能を個別の物質
に分担させた機能分離型感光体が注目されている。この
機能分離型感光体においては、それぞれの機能を有する
物質を広い範囲のものから選択し、組合せることができ
るので、高感度化、高耐久性の感光体を作製することが
可能である。このような機能分離型の感光体に使用する
電荷発生物質として、多くの物質が提案されている。中
でも、有機染料や有機顔料を電荷発生物質として用いた
感光体が近年特に注目されている。In recent years, among photoreceptors developed to improve the above-mentioned drawbacks, a functionally separated photoreceptor in which charge generation function and charge transport function are shared by separate substances has been attracting attention. In this functionally separated type photoreceptor, materials having respective functions can be selected from a wide range of materials and combined, so that it is possible to produce a photoreceptor with high sensitivity and high durability. Many materials have been proposed as charge generating materials for use in such functionally separated photoreceptors. Among these, photoreceptors using organic dyes or organic pigments as charge-generating substances have attracted particular attention in recent years.
例えば、スチリルスチルベン骨格を有するジスアゾ顔料
を用いた感光体（特開昭５３−１３３４４５号公報）、
カルバゾール骨格を有するジスアゾ顔料を用いた感光体
（特開昭５３−９５０３３号公報）、トリフェニルアミ
ン骨格を有するトリスアゾ顔料を用いた感光体（特開昭
５３−１３２３４７号公報）、ジスチリルカルバゾール
骨格を有するジスアゾ顔料を用いた感光体（特開昭５４
−１４９６７号公報）、ビススチルベン骨格を有するジ
スアゾ顔料を用いた感光体（特開昭５４−１７７３３号
公報）などが報告されている。しかし、これらの電子写
真用感光体はかならずしも要求性能を十分に満足するも
のではなく、さらに優れた感光体の開発が望まれていた
。For example, a photoreceptor using a disazo pigment having a styrylstilbene skeleton (Japanese Patent Application Laid-Open No. 133445/1983),
A photoreceptor using a disazo pigment having a carbazole skeleton (JP-A-53-95033), a photoreceptor using a trisazo pigment having a triphenylamine skeleton (JP-A-53-132347), a distyrylcarbazole skeleton A photoreceptor using a disazo pigment having
14967) and a photoreceptor using a disazo pigment having a bisstilbene skeleton (Japanese Unexamined Patent Publication No. 17733/1983). However, these photoreceptors for electrophotography do not necessarily fully satisfy the required performance, and there has been a desire to develop an even better photoreceptor.
本発明の課題は、十分な感度を有し、かつ耐久性良好な
電子写真用感光体を提供することである。An object of the present invention is to provide an electrophotographic photoreceptor having sufficient sensitivity and good durability.
本発明者らは、上記課題を解決するために鋭意検討を行
い、その結果、−形成（Ｉ）
（式中、＾ｒｌ は結合基を介して結合してもよい置換
もしくは非置換の芳香族炭化水素環または芳香族複素環
を示し、Ａｒｔは置換もしくは非置換のアントラキノン
残基を示し、Ｘはベンゼン環と縮合して芳香族炭化水素
環もしくは芳香族複素環を形成するのに必要な有機残基
を示す、）
で表されるジスアゾ化合物が既存のジスアゾ化合物に比
し、高感度および高耐久性等の優れた特性を有する電子
写真用感光体を与えることを見出し、本発明に至った。The present inventors conducted intensive studies to solve the above problems, and as a result, -formation (I) (wherein ^rl is a substituted or unsubstituted aromatic group which may be bonded via a bonding group) represents a hydrocarbon ring or an aromatic heterocycle, Art represents a substituted or unsubstituted anthraquinone residue, and X represents an organic group necessary for condensation with a benzene ring to form an aromatic hydrocarbon ring or aromatic heterocycle. The present inventors have discovered that a disazo compound represented by ) (representing a residue) provides an electrophotographic photoreceptor having superior properties such as high sensitivity and high durability compared to existing disazo compounds, and has led to the present invention. .
一般式（Ｉ）において、Ａｒｔは結合基を介して結合し
てもよい置換もしくは非置換の芳香族炭化水素環または
芳香族複素環を示すが、芳香族炭化水素環としては、ベ
ンゼン、ナフタレン、アントラセン、ピレン、フェナン
トレン、フルオレン、アントラキノン、フルオレノン、
ベンズアンスロンなどが、芳香族複素環としては、チオ
フェン、ジベンゾチオフェン、ピリジン、カルバゾール
、ベンゾオキサゾール、ベンゾチアゾールなどが挙げら
れる。また、置換基を有する場合、置換基としては、メ
チル基、エチル基、プロピル基、ブチル基などのアルキ
ル基、メトキシ基などのアルコキシ基、フェニル基、ナ
フチル基などのアリール基、ジエチルアミノ基、ジフェ
ニルアミノ基などの置換アミノ基、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、二ｌ−ｏ基
、シアノ基などが挙げられる。In the general formula (I), Art represents a substituted or unsubstituted aromatic hydrocarbon ring or aromatic heterocycle which may be bonded via a bonding group, and examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, pyrene, phenanthrene, fluorene, anthraquinone, fluorenone,
Examples of the aromatic heterocycle include benzanthrone, and examples of the aromatic heterocycle include thiophene, dibenzothiophene, pyridine, carbazole, benzoxazole, and benzothiazole. In addition, when it has a substituent, the substituent includes an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, an alkoxy group such as a methoxy group, an aryl group such as a phenyl group or a naphthyl group, a diethylamino group, or a diphenyl group. Examples include substituted amino groups such as amino groups, halogen atoms such as fluorine atoms, chlorine atoms, and bromine atoms, hydroxyl groups, dil-o groups, and cyano groups.
また、前記芳香族炭化水素環および芳香族複素環は結合
基を介して結合してもよいが、その結合基としては、−
ｏ−、−ｓ−、−ｃｏ−１−ＣＢ＝Ｃ１１−などが挙げ
られる。Further, the aromatic hydrocarbon ring and the aromatic heterocycle may be bonded via a bonding group, but the bonding group is -
Examples include o-, -s-, -co-1-CB=C11-, and the like.
本発明において好ましく使用できるＡｒｔを以下に具体
的に例示する。Art that can be preferably used in the present invention is specifically illustrated below.
１
（Ａ−９）
ＣＨｉ
へｒｔは、置換もしくは非置換のアントラキノン残基で
あり、置換基としては、メチル基、エチル基、ブチル基
などのアルキル基、メトキシ基、エトキシ基などのアル
コキシ基、ジメチルアミノ基、ジエチルアミノ基などの
ジアルキルアミノ基、アセチルアミノ基、ベンゾイルア
ミノ基などのアジルアミノ基、カルボン酸基およびその
誘導体であるカルボン酸エステル基、カルバモイル基、
フッ素原子、塩素原子、臭素原子などのハロゲン原子、
ニトロ基、シアノ基、水酸基等が挙げられる。1 (A-9) CHihert is a substituted or unsubstituted anthraquinone residue, and the substituents include an alkyl group such as a methyl group, an ethyl group, and a butyl group, an alkoxy group such as a methoxy group and an ethoxy group, dialkylamino groups such as dimethylamino group and diethylamino group, azilamino groups such as acetylamino group and benzoylamino group, carboxylic acid groups and their derivatives, carboxylic acid ester groups, carbamoyl groups,
Halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms,
Examples include nitro group, cyano group, and hydroxyl group.
Ｘがベンゼン環と縮合して形成する芳香環としては、ナ
フタレン環、アントラセン環などの炭化水素環、インド
ール環、カルバゾール環、ベンゾカルバゾール環、ジベ
ンゾフラン環などの複素環が挙げられる。またＸは置換
基を有していてもよく、置換基として塩素原子、臭素原
子などのハロゲン原子、水酸基などが挙げられる。Examples of the aromatic ring formed by condensation of X with a benzene ring include hydrocarbon rings such as a naphthalene ring and anthracene ring, and heterocycles such as an indole ring, a carbazole ring, a benzocarbazole ring, and a dibenzofuran ring. Further, X may have a substituent, and examples of the substituent include a halogen atom such as a chlorine atom and a bromine atom, and a hydroxyl group.
本発明に用いるジスアゾ化合物を、さらに具体的に第１
表に例示した。尚、表中、Ａｒ＋において（Ａ−１）〜
（Ａ−８）は前記に示した構造式であり、Ａｒ、におい
て（−）は単結合つまりアントラキノン残基の結合位置
を示す。More specifically, the disazo compound used in the present invention is
Examples are shown in the table. In addition, in the table, in Ar+ (A-1) ~
(A-8) is the structural formula shown above, and in Ar, (-) indicates a single bond, that is, a bonding position of an anthraquinone residue.
本発明の化合物は次の方法を用いて製造できる。The compounds of the present invention can be manufactured using the following method.
−形成（ＩＩ）
１１ｚＮ−Ａｒ＋−Ｎｌｌｚ （ＩＩ
）（式中、Ａｒｌ は−形成（Ｉ）に同しである。）
で表されるアミン化合物をジアゾ化し、次いでジアゾ化
された化合物をそのままあるいはホウフッ化塩として単
離した後、−形成（［［１）（式中、Ａｒｚ及びＸは一
般式（Ｉ）に同じである）で表されるカップラー化合物
とカップリングすることにより容易に製造できる。-Formation (II) 11zN-Ar+-Nllz (II
) (wherein, Arl is the same as -formation (I).)
After diazotizing the amine compound represented by and then isolating the diazotized compound as it is or as a borofluoride salt, -formation ([[1) (wherein Arz and X are the same as in general formula (I) It can be easily produced by coupling with a coupler compound represented by
本発明の電子写真用感光体は一般式（＋）で表されるジ
スアゾ化合物の少なくとも１つを電荷発生物質として導
電性支持体上の感光層に含有させてなるものである。こ
のような感光体の代表的構成は第１図や第２図に示され
る。第１図に示したのは導電性支持体１上に電荷発生物
質２と電荷輸送物質３をバインダー中に分散させた分散
タイプの感光層４を設けた感光体であり、第２図に示し
たのは導電性支持体１上に電荷発生物質をバインダー中
に分散した電荷発生層６と、電荷輸送物質をバインダー
中に分散した電荷輸送層５からなる積層タイプの感光Ｎ
４°を設けた感光体である。The electrophotographic photoreceptor of the present invention contains at least one disazo compound represented by the general formula (+) as a charge generating substance in a photosensitive layer on a conductive support. A typical structure of such a photoreceptor is shown in FIGS. 1 and 2. The photoreceptor shown in FIG. 1 is a photoreceptor in which a dispersion type photosensitive layer 4 in which a charge generating substance 2 and a charge transporting substance 3 are dispersed in a binder is provided on a conductive support 1. A laminated type photosensitive N was prepared on a conductive support 1, consisting of a charge generation layer 6 in which a charge generation substance was dispersed in a binder, and a charge transport layer 5 in which a charge transport substance was dispersed in a binder.
This is a photoreceptor with a 4° angle.
その他、電荷発生層と電荷輸送層を逆にしたもの、感光
層と導電性支持体との間に中間層を設けたものなどがあ
る。Other examples include those in which the charge generation layer and charge transport layer are reversed, and those in which an intermediate layer is provided between the photosensitive layer and the conductive support.
第２図の感光体において、像露光された光が電荷輸送層
を透過し、電荷発生層において、電荷発生物質が電荷を
発生する。生成した電荷は電荷輸送層に注入され、電荷
輸送物質が輸送を行う。In the photoreceptor shown in FIG. 2, imagewise exposed light passes through the charge transport layer, and a charge generation substance generates charges in the charge generation layer. The generated charges are injected into the charge transport layer, and the charge transport material performs the transport.
本発明の電子写真用感光体は、−ｉ式（Ｉ）のジスアゾ
化合物の外、導電性支持体、バインダー電荷輸送物質な
どを含有して構成され、感光体の他のｔｌ威要素は、感
光体の構成要素としての機能を奏するものであれば特に
限定されない。The electrophotographic photoreceptor of the present invention contains, in addition to the disazo compound of formula (I), a conductive support, a binder charge transport material, etc. It is not particularly limited as long as it functions as a body component.
すなわち、本発明の感光体において使用される導電性支
持体としては、アルミニウム、銅、亜鉛等の金属板、ポ
リエステル等のプラスチックシートまたはプラスチソク
フィルムにアルミニウム、ＳｎＯ□等の導電材料を蒸着
したもの、あるいは導電処理した紙、樹脂等が使用され
る。That is, the conductive support used in the photoreceptor of the present invention includes a metal plate made of aluminum, copper, zinc, etc., a plastic sheet made of polyester, etc., or a plastic film on which a conductive material such as aluminum, SnO□, etc. is vapor-deposited. Alternatively, conductive treated paper, resin, etc. are used.
バインダーとしては、ポリスチレン、ポリアクリルアミ
ド、ポリ−Ｎ−ビニルカルバゾールのようなビニル重合
体やボリアミド樹脂、ポリエステル樹脂、エポキシ樹脂
、フェノキシ樹脂、ポリカーボネート樹脂などの縮合樹
脂などが用いられるが、絶縁性で支持体に対する密着性
のある樹脂はいずれも使用できる。As binders, vinyl polymers such as polystyrene, polyacrylamide, and poly-N-vinylcarbazole, and condensation resins such as polyamide resins, polyester resins, epoxy resins, phenoxy resins, and polycarbonate resins are used. Any resin that is adhesive to the body can be used.
電荷輸送物質は、一般に正孔輸送物質と電子輸送物質の
二種類に分類されるが本発明の感光体には両者とも使用
することができる。正孔輸送物質としては、トリニトロ
フルオレノンあるいはテトラニトロフルオレノンなどの
電子を輸送しやすい電子受容性物質の外、ポリ−Ｎ−ビ
ニルカルバゾールに代表されるような複素環化合物を含
有する重合体、トリアゾール誘導体、オキサジアゾール
講導体、イミダゾール誘導体、ピラゾリン誘導体、ボリ
アリールアルカン誘導体、フェニレンジアミン誘導体、
ヒドラゾン誘導体、アミノ置換カルコン誘導体、トリア
リ−ルアくン誘導体、カルバゾール誘導体、スチルベン
誘導体等の正孔を輸送し易い電子供与性物質があげられ
る。Charge transport materials are generally classified into two types: hole transport materials and electron transport materials, and both can be used in the photoreceptor of the present invention. In addition to electron-accepting substances that easily transport electrons such as trinitrofluorenone or tetranitrofluorenone, examples of hole-transporting substances include polymers containing heterocyclic compounds such as poly-N-vinylcarbazole, and triazoles. derivatives, oxadiazole derivatives, imidazole derivatives, pyrazoline derivatives, polyarylalkane derivatives, phenylenediamine derivatives,
Examples include electron-donating substances that easily transport holes, such as hydrazone derivatives, amino-substituted chalcone derivatives, triaryluene derivatives, carbazole derivatives, and stilbene derivatives.
たとえば、９−エチルカルバゾール−３−アルデヒド−
１−メチル−１−フェニルヒドラゾン、９−エチルカル
バゾール−３−アルデヒド−１−ベンジル−ｌ−フェニ
ルヒドラゾン、９−エチルカルバゾール−３−アルデヒ
ド−１，１−ジフェニルヒドラゾン、４−ジェチルア５
ノスチレンーβアルデヒド−１−メチル−１−フェニル
ヒドラゾン、４−メトキシナフタレン−１−アルデヒド
ｌ−ベンジル−１−フェニルヒドラゾン、４メトキシベ
ンズアルデヒド−１−メチル−１−フェニルヒドラゾン
、２．４−ジメトキシベンズアルデヒド−１−ベンジル
−１−フェニルヒドラゾン、４−ジエチルアミノベンズ
アルデヒド−１，１−ジフェニルヒドラゾン、４−メト
キシベンズアルデヒド−１−ベンジル−１−（４−メト
キシ）フェニルヒドラゾン、４−ジフェニルアミノベン
ズアルデヒド−１−ベンジル−１−フェニルヒドラゾン
、４−ジベンジルアもノベンズアルデヒドー１．１−ジ
フェニルヒドラゾン、１．１−ビス（４ジベンジルアミ
ノフヱニル）プロパン、トリス（４−ジエチルアミノフ
ェニル）メタン、１．１−ビス（４−ジベンジルアミノ
フェニル）プロパン、２．２゛−ジメチル−４，４゛−
ビス（ジエチルアミノ）トリフェニルメタン、９− （
４−ジエチルアミノスチリル）アントラセン、９−ブロ
ム−１０（４−ジエチルアミノスチリル）アントラセン
、９−（４−ジメチルアミノベンジリデン）フルオレン
、３− （９−フルオレノンデン）−９−エチルカルバ
ゾール、１．２−ビス（４−ジエチルアミノスチリル）
ベンゼン、１，２−ビス（２，４−ジメトキシスチリル
）ベンゼン、３−スチリル−９エチルカルバゾール、３
−（４−メトキシスチリル）−９−エチルカルバゾール
、４−ジフェニルアミノスチリルヘン、４−ジベンジル
アもノスチリルベン、４−シトリルアミノスチリルベン
、１−（４−ジフェニルアミノスチリル）ナフタレン、
１−（４−ジエチルアミノスチリル）ナフタレン ４１
−シフェニルアξノーα−フェニルスチルベン、４°−
メチルフェニルアミノ−α−フェニルスチルベン、１−
フェニル−３−（４−ジエチルアミノスチリル）−５−
（４−ジエチルアミノフェニル）ビラプリン、１−フェ
ニル−３−（４−ジメチルアミノスチリル）−５−（４
−ジメチルアごジフェニル）ピラゾリンなどがある。For example, 9-ethylcarbazole-3-aldehyde-
1-Methyl-1-phenylhydrazone, 9-ethylcarbazole-3-aldehyde-1-benzyl-l-phenylhydrazone, 9-ethylcarbazole-3-aldehyde-1,1-diphenylhydrazone, 4-jethyla 5
Nostyrene-β aldehyde-1-methyl-1-phenylhydrazone, 4-methoxynaphthalene-1-aldehyde l-benzyl-1-phenylhydrazone, 4-methoxybenzaldehyde-1-methyl-1-phenylhydrazone, 2,4-dimethoxybenzaldehyde- 1-Benzyl-1-phenylhydrazone, 4-diethylaminobenzaldehyde-1,1-diphenylhydrazone, 4-methoxybenzaldehyde-1-benzyl-1-(4-methoxy)phenylhydrazone, 4-diphenylaminobenzaldehyde-1-benzyl- 1-phenylhydrazone, 4-dibenzylua and nobenzaldehyde 1.1-diphenylhydrazone, 1.1-bis(4-dibenzylaminophenyl)propane, tris(4-diethylaminophenyl)methane, 1.1-bis( 4-dibenzylaminophenyl)propane, 2,2゛-dimethyl-4,4゛-
Bis(diethylamino)triphenylmethane, 9-(
4-diethylaminostyryl)anthracene, 9-bromo-10(4-diethylaminostyryl)anthracene, 9-(4-dimethylaminobenzylidene)fluorene, 3-(9-fluorenonedene)-9-ethylcarbazole, 1.2-bis (4-diethylaminostyryl)
Benzene, 1,2-bis(2,4-dimethoxystyryl)benzene, 3-styryl-9ethylcarbazole, 3
-(4-methoxystyryl)-9-ethylcarbazole, 4-diphenylaminostyrylben, 4-dibenzyl-nostyrylben, 4-citrylaminostyrylbene, 1-(4-diphenylaminostyryl)naphthalene,
1-(4-diethylaminostyryl)naphthalene 41
-cyphenylaξno α-phenylstilbene, 4°-
Methylphenylamino-α-phenylstilbene, 1-
Phenyl-3-(4-diethylaminostyryl)-5-
(4-diethylaminophenyl) birapurine, 1-phenyl-3-(4-dimethylaminostyryl)-5-(4
-dimethylagodiphenyl)pyrazoline, etc.
この他の正孔輸送物質としては、たとえば、２．５−ビ
ス（４−ジエチルアミノフェニル）−１，３，４−オキ
サジアゾール、２．５−ビス〔４−（４−ジエチルアミ
ノスチリル）フェニル〕−１，３，４−オキサジアゾー
ル、２−（９−エチルカルバゾール−３−イル）−５−
（４−ジエチルアミノフェニル） −１，３，４−オキ
サジアゾール、２−ビニル−４−（２−クロルフェニル
）−５−（４−ジエチルアミノフェニル）オキサゾール
、２−（４−ジエチルアミノフェニル）−４−フェニル
オキサゾール、９− （３−（４−ジエチルアミノフェ
ニル）−２−プロベニリチン）−９Ｈ−キサンチン、ポ
リ−Ｎ−ビニルカルバゾール、ハロゲン化ポリ−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、ピレンホルムアルデヒド樹脂、エチルカルバ
ゾールホルムアルデヒド樹脂などが挙げられる。Other hole transport substances include, for example, 2.5-bis(4-diethylaminophenyl)-1,3,4-oxadiazole, 2.5-bis[4-(4-diethylaminostyryl)phenyl] -1,3,4-oxadiazole, 2-(9-ethylcarbazol-3-yl)-5-
(4-diethylaminophenyl) -1,3,4-oxadiazole, 2-vinyl-4-(2-chlorophenyl)-5-(4-diethylaminophenyl)oxazole, 2-(4-diethylaminophenyl)-4 -Phenyloxazole, 9-(3-(4-diethylaminophenyl)-2-probenyritin)-9H-xanthine, poly-N-vinylcarbazole, halogenated poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, pyrene formaldehyde resin , ethyl carbazole formaldehyde resin and the like.
電子輸送物質としては、たとえば、クロルアニル、ブロ
ムアニル、テトラシアノエチレン、テトラシアノキノジ
メタン、２，４．７−トリニトロ−９フルオレノン、２
．４，５．７−テトラ゛ニトロー９＝フルオレン、２，
４．５．７−チトラニトロキサントン、２．４．８−
）リニトロチオキサントン、２，６．８− ）ジニトロ
−４Ｈ−インデノ（Ｉ，２−ｂ）チオフェン−４−オン
、１，３．７− トリニトロジベンゾチオフェン−５，
５−ジオキサイドなどがある。Examples of electron transport substances include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4.7-trinitro-9fluorenone, 2
．． 4,5.7-tetranitro9=fluorene, 2,
4.5.7-Titranitroxanthone, 2.4.8-
) linitrothioxanthone, 2,6.8-) dinitro-4H-indeno(I,2-b)thiophen-4-one, 1,3.7-trinitrodibenzothiophene-5,
Examples include 5-dioxide.
これらの電荷輸送物質は単独又は２種以上混合して用い
られる。These charge transport materials may be used alone or in a mixture of two or more.
感光層と導電性支持体との間に必要に応じて中間層を設
けることができるが、材料としては、ボリアもド、ニト
ロセルロース、カゼイン、ポリビニルアルコールなどが
適当で、膜厚は１μｍ以下が好ましい。An intermediate layer can be provided between the photosensitive layer and the conductive support if necessary, and suitable materials include boria, nitrocellulose, casein, polyvinyl alcohol, etc., and the film thickness is 1 μm or less. preferable.
感光体の作製には、従来より知られた方法を用いること
ができる。たとえば積層型感光体ではジスアゾ化合物の
微粒子をバインダーを溶解した溶液中に分散し、導電性
支持体上に塗布、乾燥し、電荷発生層が得られ、次いで
、電荷輸送物質とバインダーを溶解した溶液を塗布、乾
燥することで電荷輸送層を作製できる。電荷発生層の作
製には他の方法も使用できる。たとえば、アゾ顔料を真
空蒸着する方法、あるいは、アゾ顔料の溶液を塗布、乾
燥する方法があるが、前者ではコスト高、後者では一般
に取り扱い不便な有機アミンたとえば、エチレンシアミ
ン、ｎ−ブチルアミンなどを使用するなど作製上の欠点
もあるためアゾ化合物の微粒子分散液の塗布法が好適で
ある。塗布方法は通常の手段、たとえば、ドクターブレ
ード、ディンピング、ワイヤーバーなどで行う。感光層
の厚さは、感光体の種類によりそれぞれ最適範囲は異な
る０例えば、第１図に示したような感光体では、好まし
くは３〜５０μｍ、さらに好ましくは５〜３０μｍであ
る。Conventionally known methods can be used to manufacture the photoreceptor. For example, in a laminated photoreceptor, fine particles of a disazo compound are dispersed in a solution containing a binder, coated on a conductive support, and dried to obtain a charge generation layer. A charge transport layer can be created by coating and drying. Other methods can also be used to make the charge generating layer. For example, there is a method of vacuum-depositing azo pigments, or a method of applying and drying a solution of azo pigments, but the former method is expensive, and the latter method uses organic amines such as ethylenecyamine and n-butylamine, which are generally difficult to handle. Since there are some disadvantages in production, such as the use of a fine particle dispersion of an azo compound, the coating method is preferable. Application is carried out by conventional means such as doctor blade, dipping, wire bar, etc. The optimal range of the thickness of the photosensitive layer varies depending on the type of photoreceptor. For example, in the case of a photoreceptor as shown in FIG. 1, the thickness is preferably 3 to 50 .mu.m, more preferably 5 to 30 .mu.m.
また、第２図に示したような感光体では、電荷発生Ｎ６
の厚みは好ましくは０．０１〜５μｍ、さらに好ましく
は０．０５〜２μｍである。この厚さが０．０１ ｔ！
ｍ未満では電荷の発生は十分でなく、また５μｍを越え
ると残留電位が高く実用的には好ましくない、また、電
荷輸送層５の厚みは好ましくは３〜５０μｍ１さらに好
ましくは５〜３０μｍであり、この厚さが３μｍ未満で
は帯電量が不充分であり、５Ｑｕｍを越えると残留電位
が高く実用的に好ましくない。In addition, in the photoreceptor shown in FIG. 2, charge generation N6
The thickness is preferably 0.01 to 5 μm, more preferably 0.05 to 2 μm. This thickness is 0.01t!
If the thickness is less than m, charge generation will not be sufficient, and if it exceeds 5 μm, the residual potential will be high and it is not practical, and the thickness of the charge transport layer 5 is preferably 3 to 50 μm, more preferably 5 to 30 μm, If the thickness is less than 3 .mu.m, the amount of charge is insufficient, and if it exceeds 5 .mu.m, the residual potential is high and is not practical.
一般式（Ｉ）で表されるジスアゾ化合物の感光層中の含
有量は、感光体の１１頻により異なるが、第１図に示す
ような感光体では感光層４中に好ましくは５０重量％以
下、さらに好ましくは２０重量％以下である。また、こ
の層に電荷輸送物質を好ましくは１０〜９５重量％、さ
らに好ましくは３０〜９０重量％の割合で含有させる。The content of the disazo compound represented by the general formula (I) in the photosensitive layer varies depending on the type of photoreceptor, but in the case of a photoreceptor as shown in FIG. 1, it is preferably 50% by weight or less in the photosensitive layer 4. , more preferably 20% by weight or less. Further, this layer preferably contains a charge transport material in a proportion of 10 to 95% by weight, more preferably 30 to 90% by weight.
また、第２図に示すような感光体では電荷発生層６中の
ジスアゾ化合物の割合は好ましくは３０重量％以上、さ
らに好ましくは、５０重量％以上である。また、電荷輸
送層５中には電荷輸送物質を１０〜９５重量％、好まし
くは３０〜９０重量％で含有させる。なお、この層で電
荷輸送物質が１０重量％未満であると、電荷の輸送がほ
とんど行われず、９５重量％を越えると感光体の機械的
強度が悪く実用的に好ましくない。Further, in the photoreceptor shown in FIG. 2, the proportion of the disazo compound in the charge generation layer 6 is preferably 30% by weight or more, more preferably 50% by weight or more. Further, the charge transport layer 5 contains a charge transport substance in an amount of 10 to 95% by weight, preferably 30 to 90% by weight. It should be noted that if the amount of the charge transport material in this layer is less than 10% by weight, hardly any charge will be transported, and if it exceeds 95% by weight, the mechanical strength of the photoreceptor will be poor, which is not preferred in practice.
（作用及び効果〕
本発明の電子写真用感光体は、−形成（Ｉ）で表わされ
るジスアゾ化合物を電荷発生物質として使用することに
より製造容易で、高感度でかつ反復使用に対して、性能
劣化しない優れた性能を有する。(Functions and Effects) The electrophotographic photoreceptor of the present invention is easy to manufacture by using the disazo compound represented by -formation (I) as a charge-generating substance, has high sensitivity, and exhibits performance deterioration with repeated use. It has excellent performance.
以下、実施例により本発明を具体的に説明するが、これ
により本発明の実施の態様が限定されるものではない。EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the embodiments of the present invention are not limited thereby.
製造例１
２．７−ジア藷ノフルオレノン８．０ｇを３５％塩酸２
０−及び水２５０絨に懸濁し、０°Ｃで亜硝酸ナト、リ
ウム７．９ｇを水３０Ｉ＃１に溶解した溶液を滴下した
。Production Example 1 8.0 g of 2.7-diafluorenone was dissolved in 35% hydrochloric acid 2
The suspension was suspended in 250 ml of water and a solution of 7.9 g of sodium nitrite dissolved in 30 I #1 of water was added dropwise at 0°C.
０°Ｃで１時間攪拌した後、不溶物を除去し、４２％ホ
ウフッ化水素酸８０ｍを加えた。析出した結晶を濾過、
乾燥し、ジアゾニウムホウフッ化塩１３．６ｇを得た。After stirring at 0°C for 1 hour, insoluble materials were removed and 80 m of 42% fluoroboric acid was added. Filter the precipitated crystals,
After drying, 13.6 g of diazonium borofluoride salt was obtained.
Ｎ、Ｎ−ジメチルホルムア逅ド５００ｍ１！に下記構造
式
で表されるカップラー化合物９．３ｇを加熱溶解し、酢
酸ナトリウム３．２ｇを水３０ｄに溶解した溶液を加え
た。０〜５°Ｃに冷却し、上記で得たジアゾニウムホウ
フッ化塩４．０ｇをＮ、Ｎ−ジメチルホルム７１１４０
ｍ２に溶解した溶液を滴下した。０〜５°Ｃで３０分攪
拌した後、室温で４時間攪拌した。析出物を濾取し、Ｎ
、Ｎ−ジメチルホルムアミド３００ａ＋ｆｆｉ中で固形
分をかきまぜて解いた（スラッチ）後濾過した。このス
ラッチ、濾過操作を３回繰り返した後、水洗、乾燥し、
青味黒色粉体８．２ｇ（融点２７０″Ｃ以上）を得た。500ml of N,N-dimethylformamide! 9.3 g of a coupler compound represented by the following structural formula was dissolved by heating, and a solution of 3.2 g of sodium acetate dissolved in 30 d of water was added. Cool to 0 to 5°C, and add 4.0 g of the diazonium borofluoride salt obtained above to 71140 N,N-dimethylform.
The solution dissolved in m2 was added dropwise. After stirring at 0 to 5°C for 30 minutes, the mixture was stirred at room temperature for 4 hours. The precipitate was collected by filtration, and N
The solids were stirred in N-dimethylformamide 300a+ffi (slatch) and filtered. After repeating this slatch and filtration operation three times, it was washed with water, dried,
8.2 g of bluish black powder (melting point 270″C or higher) was obtained.
このものは元素分析値及び赤外線吸収スペクトルにより
例示化合物Ｎｏ、 ３ テあることを１ｉ１１認した。This product was found to be Exemplified Compound No. 3 by elemental analysis and infrared absorption spectrum.
元素分析値 ＣＨＮ
計算値（％） ７４．２６ ３．３４ ８．２５
実測値（％） ７４．０４ ３．３３ ８．１１
赤外線吸収スペクトル（ＫＢｒ法）を第３図に示した。Elemental analysis value CHN Calculated value (%) 74.26 3.34 8.25
Actual value (%) 74.04 3.33 8.11
The infrared absorption spectrum (KBr method) is shown in FIG.
製造例２
下記構造式
で表されるカップラー化合物９．３ｇを用いた以外は製
造例１と同様に合威し、茶味黒粉体７．２ｇ（融点２７
０°Ｃ以上）を得た。このものは、元素分析値及び赤外
線吸収スペクトルより例示化合物Ｎｏ、７であることを
確認した。Production Example 2 The same procedure as Production Example 1 was used except that 9.3 g of the coupler compound represented by the following structural formula was used, and 7.2 g of brown-flavored black powder (melting point 27
0°C or higher). This product was confirmed to be Exemplified Compound No. 7 based on elemental analysis and infrared absorption spectrum.
元素分析値 計算値（％） 実測値（％） 赤外線吸収スペク た。Elemental analysis value Calculated value(%) Actual value (%) Infrared absorption spec Ta.
製造例３ 下記構造式 ％式％（ 法）を第４図に示し 赤外線吸収スペクトル（ＫＢｒ法）を第５図に示した。Manufacturing example 3 Structural formula below %formula%( method) is shown in Figure 4. The infrared absorption spectrum (KBr method) is shown in FIG.
実施例１
ポリエステル樹脂（商品名「バイロン２００ Ｊ東洋紡
製）０．５部、例示化合物Ｎｏ、３を０．５部及びテト
ラヒドロフラン５０部をボールミルで粉砕混合し、得ら
れた分散液をアルミニウム板にワイヤーバーを用いて塗
布、８０°Ｃで２０分乾燥して約１μｍの電荷発生層を
形成した。この電荷発生層上に下記構造式
で表されるカップラー化合物１０．１ｇを用いた以外は
製造例１と同様に合威し、茶味黒粉体（融点２７０°Ｃ
以上）を得た。このものは、元素分析値及び赤外線吸収
スペクトルより例示化合物Ｎｏ、 ８であることを確認
した。Example 1 0.5 parts of polyester resin (trade name: "Vylon 200 J" manufactured by Toyobo Co., Ltd.), 0.5 parts of Exemplified Compound No. 3, and 50 parts of tetrahydrofuran were pulverized and mixed in a ball mill, and the resulting dispersion was placed on an aluminum plate. It was coated using a wire bar and dried at 80°C for 20 minutes to form a charge generation layer of about 1 μm.The manufacturing process except that 10.1g of a coupler compound represented by the following structural formula was used on this charge generation layer. A brownish black powder (melting point 270°C) was obtained in the same manner as in Example 1.
above) was obtained. This product was confirmed to be Exemplified Compound No. 8 based on elemental analysis and infrared absorption spectrum.
元素分析（ＩＣＨＮＣＩ
計算値（％） ６９．５５ ２．９４ ７．７２ ６
．５３実測値（％） ６９．４１ ２．９５ ７．６
５ ６．５０で表わされるヒドラゾン化合物１部、ポリ
カーボネート樹脂（商品名「パンライ）Ｋ−１３００Ｊ
帝人化或製）１部をクロロホルム１０部に溶解した溶液
をワイヤーバーを用いて塗布、８０″Ｃで３０分乾燥し
て、厚さ約１８μｍの電荷輸送層を懲戒して、第２図に
示した積層型感光体を作製した。Elemental analysis (ICHNCI calculated value (%) 69.55 2.94 7.72 6
．． 53 Actual value (%) 69.41 2.95 7.6
5 1 part of hydrazone compound represented by 6.50, polycarbonate resin (trade name "Panrai") K-1300J
A solution prepared by dissolving 1 part of Teijin Chemical Co., Ltd.) in 10 parts of chloroform was coated using a wire bar, dried at 80''C for 30 minutes, and the charge transport layer with a thickness of about 18 μm was formed. The shown laminated photoreceptor was manufactured.
静電複写紙試験装置（■川日電機製作所製モデルＥ Ｐ
Ａ−８１００）を用いて感光体を印加電圧−６にＶの
コロナ放電により帯電させ、その時の表面電位ｖｏを測
定し、その後２秒間暗所に放置して、その時の表面電位
ｖ２を測定し、続いて感光体の表面照度が５１０×とな
る状態でハロゲンランプ（色温度２８５６°Ｋ）よりの
光を照射して、表面電位がν２の１／２になる時間を測
定し、半減露光量Ｅ１／２（ＩＬＩＸ−ｓｅｃ）を計算
した。また光照射１０秒後の表面電位ｖ１□、即ち残留
電位を測定した。Electrostatic copying paper testing device (model E P manufactured by Kawanichi Denki Seisakusho)
A-8100) was used to charge the photoreceptor to an applied voltage of -6 by corona discharge of V, the surface potential vo at that time was measured, and then the photoreceptor was left in a dark place for 2 seconds and the surface potential v2 at that time was measured. Then, with the surface illuminance of the photoreceptor at 510x, light from a halogen lamp (color temperature 2856°K) is irradiated, and the time required for the surface potential to reach 1/2 of ν2 is measured, and the half-reduced exposure amount is determined. E1/2 (ILIX-sec) was calculated. Furthermore, the surface potential v1□, ie, the residual potential, was measured after 10 seconds of light irradiation.
実施例２〜２０
電荷発生物質として本発明の化合物を、電荷輸送物質と
して、（ＣＴ−１）及び下記構造式で表わされる化合物
をそれぞれ使用し、実施例１と同様に感光体を作製し、
Ｅ１／２を求めた。使用した電荷発生物質、電荷輸送物
質および８１／２を実施例１と共に第２表に示す。Examples 2 to 20 Photoreceptors were prepared in the same manner as in Example 1, using the compound of the present invention as a charge-generating substance, and (CT-1) and a compound represented by the following structural formula as a charge-transporting substance, respectively.
E1/2 was calculated. The charge generating material, charge transporting material and 81/2 used are shown in Table 2 together with Example 1.
Ｊｓ
比較例１
特公昭５５−４２３８０号公報に記載されている下記構
造式
で表わされるジスアゾ化合物を電荷発生物質として、前
記（ＣＴ−４）を電荷輸送物質として用いた以外は実施
例１と同様に感光体を作製した。Js Comparative Example 1 Same as Example 1 except that the disazo compound represented by the following structural formula described in Japanese Patent Publication No. 55-42380 was used as the charge generating substance and the above (CT-4) was used as the charge transporting substance. A photoreceptor was fabricated.
Ｅ１／２は１２．０（ＩＬＩＸ ・５ｅｃ）であった。E1/2 was 12.0 (ILIX/5ec).
実施例２１
実施例４で作製した感光体を市販の電子写真複写装置に
装着して複写したが１万枚目においても原画に忠実なか
ぶりのない鮮明な画像が得られた。Example 21 The photoreceptor produced in Example 4 was attached to a commercially available electrophotographic copying machine to make copies, and even on the 10,000th copy, clear images without fogging that were faithful to the original images were obtained.
以上のように本発明のジスアゾ化合物を用いた電子写真
感光体は高感度でかつ繰り返し使用に安定した性能が得
られ、耐久性においても優れたものであることがいえる
。As described above, it can be said that the electrophotographic photoreceptor using the disazo compound of the present invention has high sensitivity and stable performance with repeated use, and is also excellent in durability.
本発明の感光体は電子写真複写機に利用できるばかりで
なく電子写真複写原理を応用した各種プリンター、電子
写真製版システムなどに広く利用できる。The photoreceptor of the present invention can be used not only in electrophotographic copying machines, but also in various printers, electrophotographic engraving systems, etc. that apply electrophotographic copying principles.
第１図、第２図は電子写真用感光体の構成例を示した断
面図である。
なお第１図、第２図において各符号は次の通りである。
ｉ −−−−−一導電性支持体 ４ 、４ ’ −−
−−一感光層２−・・−電荷発生物質 ５・・−・
−電荷輸送層３−・・−電荷輸送物質 ６−・−電
荷発生層第３図、第４図及び第５図はそれぞれ例示化合
物Ｎｏ、 ３、Ｎｏ、 ’７ ＆びＮｏ、 Ｂの赤外線
吸収スヘクトル（ＫＢｒ法）を示す。FIGS. 1 and 2 are cross-sectional views showing an example of the structure of an electrophotographic photoreceptor. In addition, in FIG. 1 and FIG. 2, each reference numeral is as follows. i ----- one conductive support 4, 4' --
--One photosensitive layer 2--Charge generating substance 5--
- Charge transport layer 3 - Charge transport material 6 - Charge generation layer Figures 3, 4 and 5 show infrared absorption of exemplified compounds No. 3, No. 7 & No. B, respectively. Showing the shuhector (KBr method).
Claims (1)
化学式、表等があります▼（ I ）（式中、Ａｒ＿１は
結合基を介して結合してもよい置換もしくは非置換の芳
香族炭化水素環または芳香族複素環を示し、Ａｒ＿２は
置換もしくは非置換のアントラキノン残基を示し、Ｘは
ベンゼン環と縮合して芳香族炭化水素環もしくは芳香族
複素環を形成するのに必要な有機残基を示す。） で表される少なくとも一つのジスアゾ化合物を含有する
ことを特徴とする電子写真用感光体。[Claims] 1) The photosensitive layer on the conductive support has the general formula (I)▲mathematical formula,
There are chemical formulas, tables, etc. ▼ (I) (In the formula, Ar_1 represents a substituted or unsubstituted aromatic hydrocarbon ring or aromatic heterocycle that may be bonded via a bonding group, and Ar_2 is a substituted or unsubstituted Contains at least one disazo compound represented by An electrophotographic photoreceptor characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20485389A JP2633961B2 (en) | 1989-08-09 | 1989-08-09 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20485389A JP2633961B2 (en) | 1989-08-09 | 1989-08-09 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0369962A true JPH0369962A (en) | 1991-03-26 |
| JP2633961B2 JP2633961B2 (en) | 1997-07-23 |
Family
ID=16497481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20485389A Expired - Lifetime JP2633961B2 (en) | 1989-08-09 | 1989-08-09 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2633961B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020090632A (en) * | 2018-12-07 | 2020-06-11 | 東洋インキＳｃホールディングス株式会社 | Pigment dispersant and pigment composition, colored composition and color filter using the same |
-
1989
- 1989-08-09 JP JP20485389A patent/JP2633961B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020090632A (en) * | 2018-12-07 | 2020-06-11 | 東洋インキＳｃホールディングス株式会社 | Pigment dispersant and pigment composition, colored composition and color filter using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2633961B2 (en) | 1997-07-23 |
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