JPH0417426B2 - - Google Patents
Info
- Publication number
- JPH0417426B2 JPH0417426B2 JP11911685A JP11911685A JPH0417426B2 JP H0417426 B2 JPH0417426 B2 JP H0417426B2 JP 11911685 A JP11911685 A JP 11911685A JP 11911685 A JP11911685 A JP 11911685A JP H0417426 B2 JPH0417426 B2 JP H0417426B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- formula
- represented
- substituent
- 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.)
- Expired
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 49
- 239000000049 pigment Substances 0.000 claims description 49
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000032258 transport Effects 0.000 description 37
- -1 diphenylene sulfite Chemical group 0.000 description 27
- 239000000126 substance Substances 0.000 description 18
- 238000000576 coating method Methods 0.000 description 17
- 239000010408 film Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 13
- 230000035945 sensitivity Effects 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000005018 casein Substances 0.000 description 10
- 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 10
- 235000021240 caseins Nutrition 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 238000012546 transfer Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 239000002800 charge carrier Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 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 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 238000003618 dip coating Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000005577 anthracene group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 229920001230 polyarylate Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- 230000002238 attenuated effect Effects 0.000 description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000004985 diamines Chemical class 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
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920002382 photo conductive polymer Polymers 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
- 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 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002492 poly(sulfone) Polymers 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
- 150000003219 pyrazolines Chemical class 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 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
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- WQGWMEKAPOBYFV-UHFFFAOYSA-N 1,5,7-trinitrothioxanthen-9-one Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)C3=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C3SC2=C1 WQGWMEKAPOBYFV-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
- FLQOKJWUYDGZIT-UHFFFAOYSA-N 1-methoxy-2-(2-phenylethenyl)benzene Chemical compound COC1=CC=CC=C1C=CC1=CC=CC=C1 FLQOKJWUYDGZIT-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
- FVNMKGQIOLSWHJ-UHFFFAOYSA-N 2,4,5,7-tetranitroxanthen-9-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C3OC2=C1[N+]([O-])=O FVNMKGQIOLSWHJ-UHFFFAOYSA-N 0.000 description 1
- WCQLACGUXBFKGM-UHFFFAOYSA-N 2-(2,4,7-trinitro-1-oxo-2h-fluoren-9-ylidene)propanedinitrile Chemical compound [O-][N+](=O)C1=CC=C2C(C(=CC(C3=O)[N+](=O)[O-])[N+]([O-])=O)=C3C(=C(C#N)C#N)C2=C1 WCQLACGUXBFKGM-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- CFOCDGUVLGBOTL-UHFFFAOYSA-N 2-[2-[4-(diethylamino)phenyl]ethenyl]-n,n-diethyl-1,3-benzoxazol-6-amine Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=NC2=CC=C(N(CC)CC)C=C2O1 CFOCDGUVLGBOTL-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
- 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/36—Trisazo dyes of the type
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
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- 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
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- G03G5/0679—Disazo dyes
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- G—PHYSICS
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- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
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- G03G5/02—Charge-receiving layers
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- G03G5/0664—Dyes
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- G03G5/0679—Disazo dyes
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- G—PHYSICS
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- 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
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- G—PHYSICS
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-
- 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
-
- 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
Description
〔発明の利用分野〕
本発明は電子写真感光体に関する。
〔従来の技術〕
従来より、光導電性を示す顔料や染料について
は、数多くの文献等で発表されている。
例えば“RCA Review”Vol.23，P.413〜
P.419（1962年９月）ではフタロシアニン顔料の光
導電性についての発表がなされており、又このフ
タロシアニン顔料を用いた電子写真感光体が米国
特許第3397086号公報や米国特許第3816118号公報
等に示されている。その他に、電子写真感光体に
用いる有機半導体としては、例えば米国特許第
4315983号公報、米国特許第4327169号公報や
“Reseach Disclosure”20517（1981年５月）に示
されているピリジウム系染料、米国特許第
3824099号公報に示されているスクエアリツク酸
メチン染料、米国特許第3898084号公報、米国特
許第4251613号公報等に示されたジスアゾ顔料な
どが挙げられる。
この様な有機半導体は、無機半導体に較べて合
成が容易で、しかも要求する波長域の光に対して
光導電性をもつ様な化合物として合成することが
でき、この様な有機半導体の被膜を導電性支持体
に形成した電子写真感光体は、感色性が良くなる
という利点を有しているが、感度および耐久性に
おいて実用できるものは、ごく僅かである。
〔発明の解決すべき問題点〕
本発明は、新規な有機光導電性材料を使用する
ことにより、従来にもまして優れた実用上の感度
特性及び耐久性、特に繰返し使用時における電位
特性の安定性を備えた電子写真感光体を提供すべ
くなされたものである。
〔問題点を解決するための手段及び効果〕
即ち、本発明は、導電性基体上に、下記一般式
〔〕で示されるジスアゾ顔料を含有する感光層
を有することを特徴とする電子写真感光体。
一般式〔〕
Ａ−Ｎ＝Ｎ−Ar1−NH−Ar2−Ｎ＝Ｎ−Ａ
〔〕
（式中、Ａはフエノール性OH基を有するカプラ
ー残基を表す。Ar1及びAr2は、それぞれ、置換
基を有してもよいフエニレン基、置換基を有して
もよいビフエニレン基もしくは縮合多環芳香族基
又は２価の複素環基を表す。但し、Ar1及びAr2
が、共に置換基を有していてもよいフエニレン基
であることはない。）
上記式中、縮合多環芳香族基としてはナフチレ
ン基、アンスリレン基、及びフルオレン、フルオ
レノンなどから水素２原子を除いて生ずる２価の
基などが挙げられ、２価の複素環基としては、キ
ノリン、カルバゾール、ベルゾオキサゾールなど
から水素２原子を除いて生ずる２価の基などが挙
げられる。これらAr1及びAr2で表される２価の
基を置換する原子又は基としては、例えばフツ素
原子、塩素原子、臭素原子、ヨウ素原子等のハロ
ゲン原子、メチル基、エチル基、プロピル基等の
アルキル基、ベンジル基、フエネチル基、ナフチ
ルメチル基等のアラルキル基、フエニル基、ジフ
エニル基、ナフチル基等のアリール基、メトキシ
基、エトキシ基、ブトキシ基等のアルコキシ基、
シアノ基、アセチル基、ベンゾイル基等のアシル
基、ニトロ基等が挙げられる。
但し、Ar1及びAr2が共に、置換基を有してい
てもよいフエニレン基であることはない。
また、一般式〔〕中、Ａはフエノール性OH
基を有するカプラー残基を表すが、好ましい具体
例としては下記一般式〔〕、〔〕〜〔〕で示
される基を挙げることができる。
一般式〔〕
式中、Ｘはベンゼン環と縮合して、置換基を有
していてもよい多環芳香族環（例えばナフタレン
環、アントラセン環）又はヘテロ環（例えばカル
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、ジフエニレンサ
ルフアイト環）を形成するのに必要な残基を表
す。これら環より好ましくは、ナフタレン環、ア
ントラセン環、カルバゾール環及びベンズカルバ
ゾール環である。R1及びR2は、それぞれ、水素
原子、置換基を有していてもよいアルキル基、ア
ラルキル基、アリール基又はヘテロ環基を表す
か、あるいはR1とR2とで、結合する窒素原子と
共に環状アミノ基を形成するのに必要な残基を表
す。アルキル基の具体例としてはメチル基、エチ
ル基、プロピル基、ブチル基等が挙げられる。ア
ラルキル基の具体例としては、ベンジル基、フエ
ネチル基、ナフチルメチル基等が挙げられる。ア
リール基としては、フエニル基、ジフエニル基、
ナフチル基、アンスリル基等が挙げられる。とり
わけR1を水素原子、R2をオルト位にハロゲン原
子、ニトロ基、シアノ基、トリフルオロメチル基
等の電子吸引性基及びエチル基、メチル基、ブチ
ル基等のアルキル基を有するフエニル基とした場
合に電子写真特性が特に良好である。ヘテロ環基
としてはカルバゾール、ジベンゾフラン、ベンゾ
イミダゾロン、ベンゾチアゾール、チアゾール、
ピリジン等のヘテロ環から水素１原子を除いた基
が挙げられる。
R1とR2とで形成される環状アミノ基としては、
ピロリジノ基、ピペリジノ基、モルホリノ基など
が挙げられる。
特に、一般式〔〕中、R1が水素原子であり、
R2が下記一般式［］で示されるフエニル基で
あるものが好適な例として挙げられる。
一般式［］
式中、R3は、ハロゲン原子（フツ素原子、塩
素原子、臭素原子又はヨウ素原子）、ニトロ基、
シアノ基、又はトリフルオロメチル基を表す。
また、一般式〔〕のもう１つの好適な例とし
て、下記一般式〔〕で示されるものが挙げられ
る。
一般式〔〕
式中、R4は置換基を有していてもよいフエニ
ル基を表す。
一般式〔〕
式中、R5は置換基を有していてもよいアルキ
ル基、アラルキル基又はアリール基を表す。
一般式〔〕
式中、R6は置換基を有していてもよいアルキ
ル基、アラルキル基又はアリール基を表す。
R5及びR6で表されるアルキル基の具体例とし
てはメチル基、エチル基、プロピル基、ブチル基
等が挙げられる。アラルキル基の具体例としては
ベンジル基、フエネチル基、ナフチルメチル基等
が挙げられる。アリール基としては、フエニル
基、ジフエニル基、ナフチル基、アンスリル基等
が挙げられる。
一般式〔〕、〔〕、〔〕及び〔〕中の置換
基を有していてもよい基を置換する原子又は基と
しては、例えばメチル基、エチル基、プロピル基
等のアルキル基、メトキシ基、エトキシ基、プロ
ポキシ基等のアルコキシ基、フツ素原子、塩素原
子、臭素原子、ヨウ素原子等ハロゲン原子、ニト
ロ基、シアノ基、ジメチルアミノ基、ジエチルア
ミノ基、ジベンジルアミノ基、ジフエニルアミノ
基等の置換アミノ基などが挙げられる。
一般式［］
式中、Y1は２つの窒素原子と結合した２価の
芳香族炭化水素を表すか、あるいは、
[Field of Application of the Invention] The present invention relates to an electrophotographic photoreceptor. [Prior Art] Pigments and dyes exhibiting photoconductivity have been published in numerous publications. For example, “RCA Review” Vol.23, P.413～
P.419 (September 1962), there was a presentation on the photoconductivity of phthalocyanine pigments, and electrophotographic photoreceptors using these phthalocyanine pigments were published in US Pat. No. 3,397,086, US Pat. No. 3,816,118, etc. is shown. In addition, as organic semiconductors used in electrophotographic photoreceptors, for example, US Pat.
Pyridium dyes disclosed in Publication No. 4315983, U.S. Patent No. 4327169 and “Reseach Disclosure” 20517 (May 1981), U.S. Patent No.
Examples include methine squaritate dyes shown in US Pat. No. 3,824,099, and disazo pigments shown in US Pat. No. 3,898,084 and US Pat. No. 4,251,613. Such organic semiconductors are easier to synthesize than inorganic semiconductors, and can be synthesized as compounds that have photoconductivity for light in the required wavelength range. An electrophotographic photoreceptor formed on a conductive support has the advantage of improved color sensitivity, but only a few of them are practical in terms of sensitivity and durability. [Problems to be Solved by the Invention] By using a new organic photoconductive material, the present invention achieves better practical sensitivity characteristics and durability than ever before, and in particular stability of potential characteristics during repeated use. This invention was made in order to provide an electrophotographic photoreceptor with high properties. [Means and Effects for Solving the Problems] That is, the present invention provides an electrophotographic photoreceptor comprising a photosensitive layer containing a disazo pigment represented by the following general formula [] on a conductive substrate. . General formula [] A-N=N-Ar 1 -NH-Ar 2 -N=N-A
[] (In the formula, A represents a coupler residue having a phenolic OH group. Ar 1 and Ar 2 are a phenylene group which may have a substituent, and a biphenylene group which may have a substituent, respectively) or represents a fused polycyclic aromatic group or a divalent heterocyclic group.However, Ar 1 and Ar 2
However, neither of them is a phenylene group which may have a substituent. ) In the above formula, examples of the fused polycyclic aromatic group include a naphthylene group, anthrylene group, and a divalent group formed by removing two hydrogen atoms from fluorene, fluorenone, etc., and examples of the divalent heterocyclic group include: Examples include divalent groups produced by removing two hydrogen atoms from quinoline, carbazole, benzoxazole, and the like. Examples of atoms or groups that substitute the divalent groups represented by Ar 1 and Ar 2 include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom, methyl group, ethyl group, propyl group, etc. Alkyl groups such as benzyl groups, phenethyl groups, naphthylmethyl groups, aryl groups such as phenyl groups, diphenyl groups, naphthyl groups, alkoxy groups such as methoxy groups, ethoxy groups, butoxy groups,
Examples include acyl groups such as a cyano group, an acetyl group, and a benzoyl group, and a nitro group. However, Ar 1 and Ar 2 are not both phenylene groups which may have substituents. In addition, in the general formula [], A is phenolic OH
It represents a coupler residue having a group, and preferable specific examples include groups represented by the following general formulas [] and [] to []. General formula [] In the formula, X is fused with a benzene ring to form a polycyclic aromatic ring which may have a substituent (e.g. naphthalene ring, anthracene ring) or a hetero ring (e.g. carbazole ring, benzcarbazole ring, dibenzofuran ring, benzene ring). Represents the residues necessary to form a naphthofuran ring, diphenylene sulfite ring). More preferred among these rings are a naphthalene ring, anthracene ring, a carbazole ring, and a benzcarbazole ring. R 1 and R 2 each represent a hydrogen atom, an alkyl group that may have a substituent, an aralkyl group, an aryl group, or a heterocyclic group, or the nitrogen atom bonded with R 1 and R 2 Represents a residue necessary to form a cyclic amino group together with Specific examples of the alkyl group include methyl group, ethyl group, propyl group, butyl group, and the like. Specific examples of the aralkyl group include benzyl group, phenethyl group, naphthylmethyl group, and the like. As the aryl group, phenyl group, diphenyl group,
Examples include naphthyl group and anthryl group. In particular, R 1 is a hydrogen atom, R 2 is a phenyl group having a halogen atom, an electron-withdrawing group such as a nitro group, a cyano group, a trifluoromethyl group, and an alkyl group such as an ethyl group, a methyl group, a butyl group, etc. In this case, the electrophotographic properties are particularly good. Examples of heterocyclic groups include carbazole, dibenzofuran, benzimidazolone, benzothiazole, thiazole,
Examples include groups obtained by removing one hydrogen atom from a heterocycle such as pyridine. As a cyclic amino group formed by R 1 and R 2 ,
Examples include pyrrolidino group, piperidino group, and morpholino group. In particular, in the general formula [], R 1 is a hydrogen atom,
Preferred examples include those in which R 2 is a phenyl group represented by the following general formula [ ]. General formula [] In the formula, R 3 is a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), a nitro group,
Represents a cyano group or a trifluoromethyl group. Further, another suitable example of the general formula [] is represented by the following general formula []. General formula [] In the formula, R 4 represents a phenyl group which may have a substituent. General formula [] In the formula, R 5 represents an alkyl group, an aralkyl group, or an aryl group that may have a substituent. General formula [] In the formula, R 6 represents an alkyl group, an aralkyl group, or an aryl group that may have a substituent. Specific examples of the alkyl group represented by R 5 and R 6 include a methyl group, an ethyl group, a propyl group, a butyl group, and the like. Specific examples of the aralkyl group include benzyl group, phenethyl group, naphthylmethyl group, and the like. Examples of the aryl group include phenyl group, diphenyl group, naphthyl group, and anthryl group. Examples of atoms or groups substituting optionally substituent-containing groups in general formulas [], [], [], and [] include alkyl groups such as methyl, ethyl, and propyl groups, and methoxy groups. , alkoxy groups such as ethoxy groups and propoxy groups, halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, nitro groups, cyano groups, dimethylamino groups, diethylamino groups, dibenzylamino groups, diphenylamino groups, etc. Examples include amino groups. General formula [] In the formula, Y 1 represents a divalent aromatic hydrocarbon bonded to two nitrogen atoms, or
【式】により２価のヘテロ環基を形成す
るのに必要な残基を表す。
一般式［］
式中、Y1は２つの窒素原子と結合した２価の
芳香族炭化水素を表すか、あるいは、
[Formula] represents a residue necessary to form a divalent heterocyclic group. General formula [] In the formula, Y 1 represents a divalent aromatic hydrocarbon bonded to two nitrogen atoms, or
【式】により２価のヘテロ環基を形成す
るのに必要な残基を表す。
Y1又はY2により形成される２価の芳香族炭化
水素基としては、ｏ−フエニレン基等の単環式芳
香族炭化水素の２価の基、ｏ−ナフチレン基、ペ
リナフチレン基、１，２−アンスリレン基、９，
10−フエナンスリレン基等の縮合多環式芳香族炭
化水素の２価の基が挙げられる。
またY1又はY2を含んで形成される２価のヘテ
ロ環基としては、例えば、３，４−ピラゾールジ
イル基、２，３−ピリジンジイル基、４，５−ピ
リミジンジイル基、６，７−インダゾールジイル
基、５，６−ベンズイミダゾールジイル基、６，
７−キノリンジイル基等の５〜６員環の２価の基
などが挙げられる。
一般式〔〕
一般式〔〕の中のR7及びR8は、それぞれ、
水素原子、置換基を有していてもよいフエニル
基、ナフチル基、アンスリル基、ピレニル基等の
アリール基、又は、ピリジル基、チエニル基、フ
リル基、カルバゾリル基等のヘテロ環基を表す。
R7及びR8の表すアリール基又はヘテロ環基を
置換する基としては、フツ素原子、塩素原子、臭
素原子、ヨウ素原子等ハロゲン原子、メチル基、
エチル基、プロピル基、ブチル基等のアルキル
基、メトキシ基、エトキシ基、プロポキシ基、ブ
トキシ基等のアルコキシ基、ニトロ基、シアノ
基、ジメチルアミノ基、ジエチルアミノ基、ジプ
ロピルアミノ基、ジベンジルアミノ基、ジフエニ
ルアミノ基、モルホリノ基、ピペリジノ基、ピロ
リジノ基等の置換アミノ基などが挙げられる。ま
た、R7及びR8は、結合する中心炭素と共に５〜
６員環を形成する残基を表す。この５〜６員環
は、縮合芳香族環を有していてもよい。この様な
例としては、シクロペンチリデン、シクロヘキシ
リデン、９−フルオレニリデン、９−キサンテニ
リデン等の基が挙げられる。
一般式〔〕
式〔〕中、R9及びR10は、水素原子、置換基
を有していてもよい、メチル基、エチル基、プロ
ピル基、ブチル基等のアルキル基、ベンジル基、
フエネチル基、ナフチルメチル基等のアラルキル
基、フエニル基、ナフチル基、アンスリル基、ジ
フエニル基等のアリール基、又は、カルバゾー
ル、ジベンゾフラン、ベンゾイミダゾロン、ベン
ゾチアゾール、チアゾール、ピリジン等のヘテロ
環から水素１原子を除いた基を表す。
R9及びR10を表すアルキル基、アラルキル基、
アリール基又はヘテロ環基を置換する基として
は、フツ素原子、塩素原子、臭素原子、ヨウ素原
子等ハロゲン原子、メチル基、エチル基、プロピ
ル基、ブチル基等のアルキル基、メトキシ基、エ
トキシ基、プロポキシ基、ブトキシ基等のアルコ
キシ基、ニトロ基、シアノ基、ジメチルアミノ
基、ジプロピルアミノ基、ジベンジルアミノ基、
ジフエニルアミノ基、モルホリノ基、ピペリジノ
基、ピロリジノ基等の置換アミノ基等が挙げられ
る。式(7)、(8)中のZ1及びZ2はベンゼン環と縮合し
て、ナフタレン環、アントラセン環等の多環芳香
族環、又はカルバゾール環、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、
ジフエニレンサルフアイト環等のヘテロ環を形成
するに必要な残基を示す。このうち、アントラセ
ン環、ベンズカルバゾール環、カルバゾール環と
する事がより望ましい。特にベンズカルバゾール
環は、分光感度域を長波長域にまで伸す効果が著
しく、半導体レーザー領域に高感度を有する感光
体の作成には好適である。
本発明で使用する、分子中に−NH−基を有す
る一般式〔〕のジスアゾ顔料は、この−NH−
のＨがアルキル基、アシル基、フエニル基等で置
換されたジスアゾ顔料に比べて、感度や分校感度
域、耐久安定性等電子写真特性上極めて良好な特
性を発揮させることが実験的に確かめられてい
る。
染料学的にも−NH−基の特異な深色移動効果
は良く知られているところであり、本発明の場合
もNH基が電子写真的に特殊な効果を有している
ものと推定される。また中心骨格に多環芳香環又
はヘテロ環１つ以上有することにより、キヤリア
発生効率も向上していることも寄与しているもの
と思われる。いずれにせよ、本発明によるジスア
ゾ顔料を用いた電子写真感光体を用いることによ
り、高感度化が達成され、高速の複写機やレーザ
ービームプリンター、LEDプリンター、液晶プ
リンター等への適用が可能となり、更に感光体の
前歴によらず安定した電位が確保される為、画像
的にも安定した美しい画像が得られるようになつ
た。
〔発明の具体的説明及び実施例〕
本発明で使用する、前記一般式〔〕のジスア
ゾ顔料としては、以下の顔料No.及び構造式のジス
アゾ顔料を挙げることができる。
これらのジスアゾ顔料は、１種を用いても、あ
るいは２種以上を併用してもよい。
前記一般式〔〕のジスアゾ顔料は次の様にし
て合成することができる。
即ち、一般式：
H2N−Ar1−NH−Ar2−NH2
（式中、Ar1及びAr2は前述の意味を有する。）で
示される２級アミンを有するジアミンを常法によ
りテトラゾ化し、次いで対応するカプラーをアル
カリの存在下に水素カツプリングするか、または
前記のジアミンのテトラゾリウム塩をホウフツ化
塩あるいは塩化亜鉛複塩等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等の溶媒中でアルカ
リの存在下にカツプラーとカツプリングすること
により容易に製造することができる。
次に、本発明で用いるジアゾ顔料の代表的な合
成例を下記に示す。
合成例 １
（前記例示のジスアゾ顔料No.１の合成）
500mlビーカーに水80ml濃塩酸16.6ml（0.19モ
ル）を入れ氷水浴で冷却しながらアミン
[Formula] represents a residue necessary to form a divalent heterocyclic group. The divalent aromatic hydrocarbon group formed by Y 1 or Y 2 includes divalent groups of monocyclic aromatic hydrocarbons such as o-phenylene group, o-naphthylene group, perinaphthylene group, 1,2 -Anthrylene group, 9,
Examples include divalent groups of condensed polycyclic aromatic hydrocarbons such as 10-phenanthrylene group. In addition, examples of the divalent heterocyclic group formed by containing Y 1 or Y 2 include 3,4-pyrazolediyl group, 2,3-pyridinediyl group, 4,5-pyrimidinediyl group, 6,7 -Indazolediyl group, 5,6-benzimidazolediyl group, 6,
Examples include 5- to 6-membered divalent groups such as 7-quinolinediyl group. General formula [] R 7 and R 8 in the general formula [] are each
It represents a hydrogen atom, an aryl group such as a phenyl group, a naphthyl group, an anthryl group, or a pyrenyl group, which may have a substituent, or a heterocyclic group such as a pyridyl group, a thienyl group, a furyl group, or a carbazolyl group. Examples of the group substituting the aryl group or heterocyclic group represented by R 7 and R 8 include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom, methyl group,
Alkyl groups such as ethyl group, propyl group, butyl group, alkoxy groups such as methoxy group, ethoxy group, propoxy group, butoxy group, nitro group, cyano group, dimethylamino group, diethylamino group, dipropylamino group, dibenzylamino group and substituted amino groups such as a diphenylamino group, a morpholino group, a piperidino group, and a pyrrolidino group. In addition, R 7 and R 8 are 5 to 5 along with the central carbon to which they are bonded.
Represents residues forming a 6-membered ring. This 5- to 6-membered ring may have a fused aromatic ring. Examples of such groups include groups such as cyclopentylidene, cyclohexylidene, 9-fluorenylidene, and 9-xanthenylidene. General formula [] In the formula [], R 9 and R 10 are a hydrogen atom, an alkyl group that may have a substituent such as a methyl group, an ethyl group, a propyl group, a butyl group, a benzyl group,
Hydrogen 1 from an aralkyl group such as a phenethyl group or a naphthylmethyl group, an aryl group such as a phenyl group, a naphthyl group, anthryl group, or a diphenyl group, or a heterocycle such as carbazole, dibenzofuran, benzimidazolone, benzothiazole, thiazole, or pyridine. Represents a group excluding atoms. Alkyl group, aralkyl group representing R 9 and R 10 ,
Examples of groups substituting aryl groups or heterocyclic groups include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom, alkyl groups such as methyl group, ethyl group, propyl group, butyl group, methoxy group, and ethoxy group. , alkoxy groups such as propoxy groups and butoxy groups, nitro groups, cyano groups, dimethylamino groups, dipropylamino groups, dibenzylamino groups,
Substituted amino groups such as diphenylamino group, morpholino group, piperidino group, and pyrrolidino group are mentioned. Z 1 and Z 2 in formulas (7) and (8) are fused with a benzene ring to form a polycyclic aromatic ring such as a naphthalene ring or anthracene ring, or a carbazole ring, benzcarbazole ring, dibenzofuran ring, or benzonaphthofuran ring. ring,
Residues necessary to form a heterocycle such as a diphenylene sulfite ring are shown. Among these, an anthracene ring, a benzcarbazole ring, and a carbazole ring are more preferable. In particular, the benzcarbazole ring has a remarkable effect of extending the spectral sensitivity range to a long wavelength range, and is suitable for producing a photoreceptor having high sensitivity in the semiconductor laser range. The disazo pigment of the general formula [] having an -NH- group in the molecule used in the present invention is the -NH-
It has been experimentally confirmed that compared to disazo pigments in which H is substituted with an alkyl group, acyl group, phenyl group, etc., it exhibits extremely good electrophotographic properties such as sensitivity, separation sensitivity range, and durability stability. ing. The unique bathochromic transfer effect of the -NH- group is well known from the perspective of dyes, and it is presumed that the NH group has a special electrophotographic effect in the present invention as well. . It is also believed that having one or more polycyclic aromatic rings or heterocycles in the central skeleton also contributes to improved carrier generation efficiency. In any case, by using the electrophotographic photoreceptor using the disazo pigment according to the present invention, high sensitivity can be achieved and it can be applied to high-speed copying machines, laser beam printers, LED printers, liquid crystal printers, etc. Furthermore, since a stable potential is ensured regardless of the prior history of the photoreceptor, stable and beautiful images can now be obtained. [Specific Description and Examples of the Invention] Examples of the disazo pigment of the general formula [] used in the present invention include disazo pigments of the following pigment numbers and structural formulas. These disazo pigments may be used alone or in combination of two or more. The disazo pigment of the general formula [] can be synthesized as follows. That is, a diamine having a secondary amine represented by the general formula: H 2 N-Ar 1 -NH-Ar 2 -NH 2 (wherein Ar 1 and Ar 2 have the above-mentioned meanings) is tetrazotized by a conventional method. and then the corresponding coupler is hydrogen-coupled in the presence of an alkali, or once the tetrazolium salt of the diamine is isolated in the form of a borofluoride salt or zinc chloride double salt, etc., a suitable solvent such as N,N - It can be easily produced by coupling with a coupler in the presence of an alkali in a solvent such as dimethylformamide or dimethyl sulfoxide. Next, a typical synthesis example of the diazo pigment used in the present invention is shown below. Synthesis Example 1 (Synthesis of Disazo Pigment No. 1 exemplified above) Add 80 ml of water and 16.6 ml (0.19 mol) of concentrated hydrochloric acid to a 500 ml beaker and add amine while cooling in an ice water bath.
【式】7.23ｇ
（0.029モル）撹拌し液温を３℃とした。次に亜硝
酸ソーダ4.1ｇ（0.060モル）を水７mlに溶かした
液を液温を３〜10℃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
攪拌した。反応液にカーボンを加え濾過してテト
ラゾ化液を得た。
次に、２ビーカーにジメチルホルムアミド
700mlを入れトリエチルアミン53.6（0.53モル）を
加え
３−ヒドロキシ−２−ナフトエ酸アニリド
16.06ｇ（0.061モル）を添加して溶解した。
このカプラー溶液を６℃に冷却し液温を６〜10
℃にコントロールしながら前述のテトラゾ化液を
30分かけて撹拌下滴下して、その後室温で２時間
撹拌し更に１晩放置した。反応液を濾過後水洗濾
過し固型分換算で粗製顔料21.5ｇの水ペーストを
得た。
次に400mlのＮ，Ｎ−ジメチルホルムアミドを
用い室温で撹拌濾過を４回繰り返した。その後
400mlのメチルエチルケトンでそれぞれ２回撹拌
濾過を繰り返した後室温で減圧乾燥し精製顔料
19.9ｇを得た。収率は86.0％であつた。融点＞
250゜
元素分析 計算値(%) 実験値(%)
Ｃ 75.27 75.30
Ｈ 4.42 4.37
Ｎ 12.29 12.25
以上代表的な顔料の合成法について述べたが一
般式(1)で示される他のジスアゾ顔料も同様にして
合成される。
前述のジスアゾ顔料を含有する被覆は光導電性
を示し、電子写真感光体の感光層に用いるのに適
している。
すなわち、本発明の具体例では導電性支持体の
上に前述のジ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中に分散
含有させて被膜形成することにより電子写真感光
体を調製することができる。
本発明の好ましい具体例では、電子写真感光体
の感光層を電荷発生層と電荷輸送層とに機能分離
した電子写真感光体における電荷発生層として、
前述の光導電性被膜を適用することができる。
電荷発生層は、十分な吸光度を得るために、で
きる限り多くの前述のジスアゾ顔料を含有し、且
つ発生した電荷キヤリアの飛程を短かくするため
に薄膜層、例えば5μ以下、好ましくは0.01〜1μの
厚みをもつ薄膜層とすることが好ましい。このこ
とは、入射光量の大部分が電荷発生層で吸収され
て、多くの電荷キヤリアを生成すること、さらに
発生した電荷キヤリアを再結合や捕獲（トラツ
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。
電荷発生層は、前述のジ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
ことによつて形成でき、また真空蒸着装置により
蒸着膜を形成することによつても得ることができ
る。電荷発生層を塗工によつて形成する際に用い
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、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、ポリアリレート（ビスフ
エノールＡとフタル酸の縮重合体など。）、ポリカ
ーボネート、ポリエステル、フエノキシ樹脂、ポ
リ酢酸ビニル、アクリル樹脂、ポリアクリルアミ
ド樹脂、ポリアミド、ポリビニルピリジン、セル
ロース系樹脂、ウレタン樹脂、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、80重量％以下、
好ましくは40重量％以下が適している。
これらの樹脂を溶解する溶剤は、樹脂の種類に
よつて異なり、また下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。具
体的な有機溶剤としては、メタノール、エタノー
ル、イソプロパノ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樹脂族ハロゲン
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類などを用いることがで
きる。
塗工は、浸漬コーテイング法、スプレーコーテ
イング法、スピンナーコーテイング法、ビードコ
ーテイング法、マイナーバーコーテイング法、ブ
レードコーテイング法、ローラーコーテイング
法、カーテンコーテイング法などのコーテイング
法を用いて行なうことができる。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。
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
入された電荷キヤリアを受け取るとともに、これ
らの電荷キヤ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。
電荷輸送層が電荷発生層の上に形成される場合
電荷輸送層における電荷キヤリアを輸送する物質
（以下、単に電荷輸送物質という）は、前述の電
荷発生層が感応する電磁波の波長域に実質的に非
感応性であることが好ましい。ここで言う「電磁
波」とは、ｒ線、Ｘ線、紫外線、可視光線、近赤
外線、赤外線、遠赤外線などを包含する広義の
「光線」の定義を包含する。電荷輸送層の光感応
性波長域が電荷発生層のそれと一致またはオーバ
ーラツプする時には、両者で発生した電荷キヤリ
アが相互に捕獲し合い、結果的には感度の低下の
原因となる。
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、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−９−フルオレノン、２，４，７−
トリニトロ−９−ジシアノメチレンフルオレノ
ン、２，４，５，７−テトラニトロキサントン、
２，４，８−トリニトロチオキサントン等の電子
吸引性物質やこれら電子吸引性物質を高分子化し
たもの等がある。
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−Ｎ−クエニルヒドラジノ−３−メチ
リデン−９−エチルカルバゾール、Ｎ，Ｎ−ジフ
エニルヒドラジノ−３−メチリデン−９−エチル
カルバゾール、Ｎ，Ｎ−ジフエニルヒドラジノ−
３−メチリデン−10−エチルフエノチアジン、
Ｎ，Ｎ−ジフエニルヒドラジノ−３−メチリデン
−10−エチルフエノキサジン、ｐ−ジエチルアミ
ノベンズアルデヒド−Ｎ，Ｎ−ジフエニルヒドラ
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−フエニルヒドラゾン、ｐ−
ピロリジノベンズアルデヒド−Ｎ，Ｎ−ジフエニ
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−ジフエニルヒド
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−ヒドラゾン等のヒ
ドラゾン類、２，５−ビス（ｐ−ジエチルアミノ
フエニル）−１，３，４−オキサジアゾール、１
−フエニル−３−（ｐ−ジエチルアミノスチリル）
−５−（ｐ−ジエチルアミノフエニル）ピラゾリ
ン、１−〔キノリル(2)〕−３−（ｐ−ジエチルアミ
ノスチリル）−５−（ｐ−ジエチルアミノフエニ
ル）ピラゾリン、１−〔ピリジル(2)〕−３−（ｐ−
ジエチルアミノスチリル）−５−（ｐ−ジエチルア
ミノフエニル）ピラゾリン、１−〔６−メトキシ
−ピリジル(2)〕−３−（ｐ−ジエチルアミノスチリ
ル）−５−（ｐ−ジエチルアミノフエニル）ピラゾ
リン、１−〔ピリジル(3)〕−３−（ｐ−ジエチルア
ミノスチリル）−５−（ｐ−ジエチルアミノフエニ
ル）ピラゾリン、１−〔レピジル(2)〕−３−（ｐ−
ジエチルアミノスチリル）−５−（ｐ−ジエチルア
ミノフエニル）ピラゾリン、１−〔ピリジル(2)〕−
３−（ｐ−ジエチルアミノスチリル）−４−メチル
−５−（ｐ−ジエチルアミノフエニル）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
ミノフエニル）ピラゾリン、１−フエニル−３−
（ｐ−ジエチルアミノスチリル）−４−メチル−５
−（ｐ−ジエチルアミノフエニル）ピラゾリン、
１−フエニル−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
エニル）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−ジエチルアミノベンズオキサゾール、２−
（ｐ−ジエチルアミノフエニル）−４−（ｐ−ジメ
チルアミノフエニル）−５−（２−クロロフエニ
ル）オキサゾール等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−ジエチル
アミノベンゾチアゾール等のチアゾール系化合
物、ビス（４−ジエチルアミノ−２−メチルフエ
ニル）−フエニルメタン等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−メチルフエニル）ヘプタン、１，
１，２，２−テトラキス（４−Ｎ，Ｎ−ジメチル
アミノ−２−メチルフエニル）エタン等のポリア
リールアルカン類、４−ジフエニルアミノ−4′−
メトキシスチルベン、4′−ジエチルアミノスチリ
ル−３−（９−エチル）カルバゾール等のスチル
ベン系化合物、トリフエニルアミン、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−ビニルフエニルアントラセン、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
アルデヒド樹脂等がある。
これらの有機電荷輸送物質の他に、セレン、セ
レン−テルル、アモルフアスシリコン、硫化カド
ミウムなどの無機材料も用いることができる。
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。
電荷輸送物質に成膜性を有していない時には、
適当なバインダーを選択することによつて被膜形
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、ポリアリレート、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−ブタジエンコポリマー、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を挙げることが
できる。
電荷輸送層は、電荷キヤ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、５〜30μであるが、好まし
い範囲は８〜20μである。塗工によつて電荷輸送
層を形成する際には、前述した様な適当なコーテ
イング法を用いることができる。
この様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、パナジウ
ム、モリブデン、クロム、チタン、ニツケル、イ
ンジウム、金や白金などを用いることができ、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つて被覆形成された層を有
するプラスチツク（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、ポリフツ化エチレンな
ど）、導電性粒子（例えば、アルミナ粉末、酸化
スズ、酸化亜鉛、酸化チタン、カーボンブラツ
ク、銀粒子など）を適当なバインダーとともにプ
ラスチツク又は前記導電性基体の上に被覆した基
体、導電性粒子をプラスチツ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ツクなどを
用いることができる。
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
610、共重合ナイロン、アルコキシメチル化ナイ
ロンなど）、ポリウレタン、ゼラチン、酸化アル
ミニウムなどによつて形成できる。
下引層の膜厚は、0.1〜5μ、好ましくは0.5〜3μ
が適当である。
導電層、電荷発生層、電荷輸送層の順に積層し
た感光体を使用する場合において電荷輸送物質が
電子輸送性物質からなるときは、電荷輸送層表面
を正に帯電する必要があり、帯電後露光すると露
光部では電荷発生層において生成した電子が電荷
輸送層に注入され、そのあと表面に達して正電荷
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。この様にしてでき
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ツクフイルム等に転写
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
に転写後現像し、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良く、特定のものに
限定されるものではない。
一方、電荷輸送物質が正孔輸送物質から成る場
合、電荷輸送層表面を負に帯電する必要があり、
帯電後、露光すると露送部では電荷発生層におい
て生成した正孔が電荷輸送層に注入され、その後
表面に達して負電荷を中和し、表面電位の減衰が
生じ未露光部との間に静電コントラストが生じ
る。現像時には電子輸送性物質を用いた場合とは
逆に正電荷性トナーを用いる必要がある。
導電層・電荷輸送層・電荷発生層の順に積層し
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、電荷発生層表
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電
子は電荷輸送層に注入されそのあと基盤に達す
る。一方電荷発生層において生成した正孔は表面
に達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。この様にしてできた静
電潜像を正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ツクフイルム等に転写後現像
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現像し、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。
一方電荷発生層が正孔輸送性物質からなるとき
は、電荷発生層表面を正に帯電する必要があり、
帯電後露光すると露光部では電荷発生層において
生成した正孔は電荷輸送層に注入されその後基盤
に達する。一方電荷発生層において生成した電子
は表面に達した表面電位の減衰が生じ未露光部と
の間にコントラストが生じる。現像時には電子輸
送性物質を用いた場合とは逆に負電荷性トナーを
用いる必要がある。
また、本発明の別の具体例では、前述のヒドラ
ゾン類、ピラゾリン類、オキサゾール類、チアゾ
ール類、トリアリールメタン類、ポリアリールア
ルカン類、トリフエニルアミン、ポリ−Ｎ−ビニ
ルカルバゾール類など有機光導電性物質や酸化亜
鉛、硫化カドミウム、セレンなどの無機光導電性
物質の増感剤として前述のジスアゾ顔料を含有さ
せた感光被膜とすることができる。この感光被膜
は、これらの光導電性物質と前述のジスアゾ顔料
をバインダーとともに塗工によつて被膜形成され
る。
本発明の別の具体例としては前述の電荷輸送物
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。この際、前述の電荷輸送物
質の他にポリ−Ｎ−ビニルカルバゾールとトリニ
トロフルオレノンからなる電荷移動錯体化合物を
用いることができる。この例の電子写真感光体は
前述のジスアゾ顔料と電荷移動錯体化合物をテト
ラヒドロフランに溶解させたポリエステル溶液中
に分散させた後、被膜形成させて調製できる。
いずれの感光体においても用いる顔料は一般式
(1)で示されるジスアゾ顔料から選ばれる少なくと
も一種類の顔料を含有しその結晶形は非晶質であ
つても結晶質であつてもよい。
又必要に応じて光吸収の異なる顔料を組合せて
使用し感光体の感度を高めたり、パンクロマチツ
クな感光体を得るなどの目的で一般式(1)で示され
るジスアゾ顔料を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。
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、LEDプリンター、液晶プリンター、
レーザー製版等の電子写真応用分野にも広く用い
る事ができる。
以下本発明を実施例によつて説明する。
実施例 １〜40
アルミ板上にカゼインのアンモニア水溶液（カ
ゼイン11.2％、アンモニア水１ｇ、水222ml）を
マイヤーバーで乾燥後の膜厚が1.0μとなる様に塗
布し乾燥した。
次に前記例示のジスアゾ顔料No.１ ５ｇをエタ
ノール9.5mlにブチラール樹脂（ブチラール化度
63モル％）２ｇを溶かした液に加えサンドミルで
２時間分散した。この分散液を先に形成したカゼ
イン層の上に乾燥後の膜厚が0.5μとなる様にマイ
ヤーバーで塗布し乾燥して電荷発生層を形成し
た。次いで構造式
のヒドラゾン化合物５ｇとポリメチルメタクリレ
ート樹脂（数平均分子量100000）５ｇをベンゼン
70mlに溶解しこれを電荷発生層の上に乾燥後の膜
厚が12μとなる様にマイヤーバーで塗布し乾燥し
て電荷輸送層を形成し実施例１の感光体を作成し
た。ジスアゾ顔料No.１に代えて第一表に示す他の
例示顔料を用いた実施例２〜40に対応する感光体
を全く同様にして作成した。
この様にして作成した電子写真感光体を川口電
機(株)製静電複写紙試験装置Model SP−428を用
いてスタテイツク方式で−5kVでコロナ帯電し暗
所で１秒間保持した後照度2luxで露光し帯電特性
を調べた。
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（E1/2）を測定した。この結果を第一表に示
す。[Formula] 7.23g (0.029mol) was stirred and the liquid temperature was brought to 3°C. Next, a solution prepared by dissolving 4.1 g (0.060 mol) of sodium nitrite in 7 ml of water was added dropwise over 10 minutes while controlling the temperature within the range of 3 to 10°C, and after the addition was completed, the mixture was stirred for an additional 30 minutes at the same temperature. Carbon was added to the reaction solution and filtered to obtain a tetrazotized solution. Next, add dimethylformamide to 2 beakers.
Pour 700ml and add 53.6 (0.53 mol) of triethylamine. 3-Hydroxy-2-naphthoic acid anilide.
16.06 g (0.061 mol) was added and dissolved. Cool this coupler solution to 6℃ and reduce the liquid temperature to 6-10℃.
Add the above-mentioned tetrazotization solution while controlling the temperature at
The mixture was added dropwise over 30 minutes with stirring, and then stirred at room temperature for 2 hours and further left overnight. The reaction solution was filtered, washed with water, and filtered to obtain a water paste containing 21.5 g of crude pigment in terms of solid content. Next, stirring filtration was repeated four times at room temperature using 400 ml of N,N-dimethylformamide. after that
After repeating stirring and filtration twice with 400ml of methyl ethyl ketone, dry under reduced pressure at room temperature to obtain purified pigment.
19.9g was obtained. The yield was 86.0%. Melting point>
250゜ Elemental analysis Calculated value (%) Experimental value (%) C 75.27 75.30 H 4.42 4.37 N 12.29 12.25 The synthesis method of typical pigments has been described above, but other disazo pigments represented by general formula (1) can also be synthesized in the same way. are synthesized. Coatings containing the aforementioned disazo pigments exhibit photoconductivity and are suitable for use in photosensitive layers of electrophotographic photoreceptors. That is, in a specific example of the present invention, an electrophotographic photoreceptor is prepared by forming a film of the above-mentioned disazo pigment on a conductive support by vacuum evaporation, or by dispersing it in a suitable binder and forming a film. can do. In a preferred embodiment of the present invention, as a charge generation layer in an electrophotographic photoreceptor in which the photosensitive layer of the electrophotographic photoreceptor is functionally separated into a charge generation layer and a charge transport layer,
Photoconductive coatings as described above can be applied. The charge generation layer contains as much of the above-mentioned disazo pigment as possible in order to obtain sufficient absorbance, and is a thin film layer, for example, 5μ or less, preferably 0.01~ to shorten the range of the generated charge carriers. Preferably, it is a thin film layer with a thickness of 1μ. This means that most of the incident light is absorbed by the charge generation layer, generating many charge carriers, and that the generated charge carriers are not deactivated by recombination or trapping, but are transferred to the charge transport layer. This is due to the need for injection. The charge generation layer can be formed by dispersing the above-mentioned disazo pigment in a suitable binder and coating it on the substrate, or it can also be obtained by forming a vapor deposited film using a vacuum vapor deposition device. I can do it. The binder used when forming 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, ribinyanthracene, and polyvinylpyrene. . Preferably,
Polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.), polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyridine, cellulose resin, urethane resin, Examples include insulating resins such as epoxy resin, casein, polyvinyl alcohol, and polyvinylpyrrolidone.
The resin contained in the charge generation layer is 80% by weight or less,
Preferably, 40% by weight or less is suitable. 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 or undercoat layer described below. Specific organic solvents include alcohols such as methanol, ethanol, and isopropanol, ketones such as acetone, methyl ethyl ketone, and cyclohexane, N,N-dimethylformamide,
Amides such as 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, and resin group halogens such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, and trichloroethylene. Hydrocarbons or aromatics such as benzene, toluene, xylene, ligroin, monochlorobenzene, dichlorobenzene, etc. can be used. Coating can be carried out using coating methods such as dip coating, spray coating, spinner coating, bead coating, minor bar coating, blade coating, roller coating, and curtain coating. For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying at a temperature of 30℃ to 200℃ for 5 minutes to 2
It can be carried out stationary or under blown air for a period of time within a range of hours. The charge transport layer is electrically connected to the charge generation layer described above, and has the function of receiving charge carriers injected from the charge generation layer in the presence of an electric field and transporting these charge carriers to the surface. ing. At this time, this charge transport layer may be laminated on or under the charge generation layer. When a charge transport layer is formed on a charge generation layer, the substance that transports charge carriers in the charge transport layer (hereinafter simply referred to as a charge transport substance) is substantially in the wavelength range of electromagnetic waves to which the charge generation layer is sensitive. Preferably, it is insensitive to. The term "electromagnetic waves" used herein includes a broad definition of "light rays" including r-rays, X-rays, ultraviolet rays, visible light, near-infrared rays, infrared rays, far-infrared rays, and the like. When the photosensitive wavelength range of the charge transport layer coincides with or overlaps that of the charge generation layer, charge carriers generated in both trap each other, resulting in a decrease in sensitivity. Charge transport substances include electron transport substances and hole transport substances, and electron transport substances include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane, and 2,4,7-trinitro-9-fluorenone. , 2, 4, 5, 7-
Tetranitro-9-fluorenone, 2,4,7-
trinitro-9-dicyanomethylenefluorenone, 2,4,5,7-tetranitroxanthone,
Examples include electron-withdrawing substances such as 2,4,8-trinitrothioxanthone, and polymerization of these electron-withdrawing substances. Examples of hole-transporting substances include pyrene, N-ethylcarbazole, N-isopropylcarbazole,
N-Methyl-N-quenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-
3-methylidene-10-ethylphenothiazine,
N,N-diphenylhydrazino-3-methylidene-10-ethylphenoxazine, 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-methylbenzthiazolinone-2-hydrazone hydrazones such as 2,5-bis(p-diethylaminophenyl)-1,3,4-oxadiazole, 1
-Phenyl-3-(p-diethylaminostyryl)
-5-(p-diethylaminophenyl)pyrazoline, 1-[quinolyl(2)]-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[pyridyl(2)]- 3-(p-
diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[6-methoxy-pyridyl(2)]-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1- [Pyridyl(3)]-3-(p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[Lepidyl(2)]-3-(p-
diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-[pyridyl(2)]-
3-(p-diethylaminostyryl)-4-methyl-5-(p-diethylaminophenyl)pyrazoline, 1-[pyridyl(2)]-3-(α-methyl-p-
diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-phenyl-3-
(p-diethylaminostyryl)-4-methyl-5
-(p-diethylaminophenyl)pyrazoline,
1-phenyl-3-(α-benzyl-p-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, spiropyrazoline and other pyrazolines, 2-(p-diethylaminostyryl)
-6-diethylaminobenzoxazole, 2-
Oxazole compounds such as (p-diethylaminophenyl)-4-(p-dimethylaminophenyl)-5-(2-chlorophenyl)oxazole, 2
Thiazole compounds such as -(p-diethylaminostyryl)-6-diethylaminobenzothiazole, triarylmethane compounds such as bis(4-diethylamino-2-methylphenyl)-phenylmethane, 1,1-bis(4-N,N -diethylamino-2-methylphenyl)heptane, 1,
Polyarylalkanes such as 1,2,2-tetrakis(4-N,N-dimethylamino-2-methylphenyl)ethane, 4-diphenylamino-4'-
Stilbene compounds such as methoxystilbene, 4'-diethylaminostyryl-3-(9-ethyl)carbazole, triphenylamine, poly-N-
Examples include vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, poly-9-vinylphenylanthracene, pyrene-formaldehyde resin, and ethylcarbazole formaldehyde resin. In addition to these organic charge transport materials, inorganic materials such as selenium, selenium-tellurium, amorphous silicon, and cadmium sulfide can also be used. Moreover, these charge transport substances may be one or two types.
More than one species can be used in combination. When the charge transport material does not have film-forming properties,
A film can be formed by selecting an appropriate binder. Resins that can be used as binders are:
For example, insulating resins such as acrylic resin, polyarylate, polyester, polycarbonate, polystyrene, acrylonitrile-styrene copolymer, acrylonitrile-butadiene copolymer, polyvinyl butyral, polyvinyl formal, polysulfone, polyacrylamide, polyamide, chlorinated rubber, or poly-N- Mention may be made of organic photoconductive polymers such as vinylcarbazole, polyvinylanthracene, polyvinylpyrene. Since the charge transport layer has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary. Generally, it is 5-30μ, but the preferred range is 8-20μ. When forming the charge transport layer by coating, an appropriate coating method as described above can be used. 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. As the substrate having the conductive layer, materials that are conductive themselves such as aluminum, aluminum alloy, copper, zinc, stainless steel, panadium, molybdenum, chromium, titanium, nickel, indium, gold, and platinum can be used. In addition, plastics (e.g., polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic) have a layer coated with aluminum, aluminum alloy, indium oxide, tin oxide, indium oxide-tin oxide alloy, etc. by vacuum deposition method. resin, polyethylene fluoride, etc.), conductive particles (e.g., alumina powder, tin oxide, zinc oxide, titanium oxide, carbon black, silver particles, etc.) together with a suitable binder on plastic or the aforementioned conductive substrate. A substrate made of plastic or paper impregnated with conductive particles, a plastic containing a conductive polymer, etc. can be used. A subbing layer having barrier and adhesive functions can also be provided between the conductive layer and the photosensitive layer. The subbing layer is made of casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer, polyamide (nylon 6, nylon 66, nylon
610, copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin, aluminum oxide, etc. The thickness of the undercoat layer is 0.1 to 5μ, preferably 0.5 to 3μ.
is appropriate. When using a photoreceptor in which a conductive layer, a charge generation layer, and a charge transport layer are laminated in this order, and the charge transport material is an electron transport material, the surface of the charge transport layer must be positively charged, and exposure after charging is required. Then, in the exposed area, 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 with the unexposed area. . A visible image can be 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, plastic film, etc. 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, then developed and fixed. The type of developer, the developing method, and the fixing method may be any known ones or known methods, and are not limited to specific ones. On the other hand, when the charge transport material consists of a hole transport material, the surface of the charge transport layer must be negatively charged.
After charging, when exposed to light, holes generated in the charge generation layer in the exposed area are injected into the charge transport layer, and then reach the surface and neutralize the negative charge, resulting in attenuation of the surface potential and a gap between the exposed area and the unexposed area. Electrostatic contrast occurs. During development, it is necessary to use a positively charged toner, contrary to the case where an electron transporting substance is used. When using a photoreceptor in which a conductive layer, a charge transport layer, and a charge generation layer are laminated in this order, if the charge transport material is an electron transport material, the surface of the charge generation layer must be negatively charged, and after charging Upon exposure, in the exposed portion, electrons generated in the charge generation layer are injected into the charge transport layer and then reach the substrate. On the other hand, holes generated in the charge generation layer reach the surface and the surface potential is attenuated, creating an electrostatic contrast with the unexposed area. A visible image can be obtained by developing the electrostatic latent image thus formed with a positively charged toner. This can be directly fixed, or the toner image can be transferred to paper, plastic film, etc. 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, then developed 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. On the other hand, when the charge generation layer is made of a hole transporting substance, the surface of the charge generation layer must be positively charged.
When exposed to light after charging, holes generated in the charge generation layer in the exposed area are injected into the charge transport layer and then reach the substrate. On the other hand, when the electrons generated in the charge generation layer reach the surface, the surface potential is attenuated, creating a contrast with the unexposed area. During development, it is necessary to use a negatively charged toner, contrary to the case where an electron transporting substance is used. In another specific example of the present invention, organic photoconductive materials such as the aforementioned hydrazones, pyrazolines, oxazoles, thiazoles, triarylmethanes, polyarylalkanes, triphenylamines, poly-N-vinylcarbazoles, etc. The photosensitive film may contain the above-mentioned disazo pigment as a sensitizer for photoconductive substances and inorganic photoconductive substances such as zinc oxide, cadmium sulfide, and selenium. This photosensitive film is formed by coating these photoconductive substances and the above-mentioned disazo pigment together with a binder. Another specific example of the present invention is an electrophotographic photoreceptor in which the above-mentioned charge transporting material is contained in the same layer. At this time, a charge transfer complex compound consisting of poly-N-vinylcarbazole and trinitrofluorenone can be used in addition to the above-mentioned charge transport substance. The electrophotographic photoreceptor of this example can be prepared by dispersing the aforementioned disazo pigment and charge transfer complex compound in a polyester solution in tetrahydrofuran, and then forming a film thereon. The pigment used in both photoreceptors has the general formula
It contains at least one type of pigment selected from the disazo pigments shown in (1), and its crystal form may be amorphous or crystalline. Furthermore, if necessary, two or more types of disazo pigments represented by the general formula (1) may be used in combination for the purpose of increasing the sensitivity of the photoreceptor or obtaining a panchromatic photoreceptor by using a combination of pigments with different light absorptions. Alternatively, it can be used in combination with a charge generating substance selected from known dyes and pigments. The electrophotographic photoreceptor of the present invention can be used not only for electrophotographic copying machines, but also for laser printers and CRTs.
Printers, LED printers, LCD printers,
It can also be widely used in electrophotographic applications such as laser engraving. The present invention will be explained below with reference to Examples. Examples 1 to 40 An ammonia aqueous solution of casein (11.2% casein, 1 g of aqueous ammonia, 222 ml of water) was coated on an aluminum plate using a Mayer bar so that the film thickness after drying was 1.0 μm and dried. Next, 5 g of the above-mentioned disazo pigment No. 1 was added to 9.5 ml of ethanol with butyral resin (butyralization degree).
63 mol%) was added to the solution and dispersed for 2 hours using a sand mill. This dispersion was applied onto the previously formed casein layer using a Mayer bar so that the film thickness after drying was 0.5 μm, and dried to form a charge generation layer. Then the structural formula 5 g of hydrazone compound and 5 g of polymethyl methacrylate resin (number average molecular weight 100,000) were added to benzene.
The photoreceptor of Example 1 was prepared by dissolving the solution in 70 ml and coating it on the charge generation layer using a Mayer bar so that the thickness after drying would be 12μ, and drying to form a charge transport layer. Photoreceptors corresponding to Examples 2 to 40 were prepared in exactly the same manner using other exemplary pigments shown in Table 1 in place of disazo pigment No. 1. The electrophotographic photoreceptor thus prepared was statically charged with corona at -5 kV using an electrostatic copying paper tester Model SP-428 manufactured by Kawaguchi Electric Co., Ltd., and held in a dark place for 1 second, then at an illuminance of 2 lux. It was exposed to light and its charging characteristics were investigated. As for the charging characteristics, the surface potential (Vo) and the exposure amount (E 1/2 ) required to attenuate the potential by 1/2 when dark decaying for 1 second were measured. The results are shown in Table 1.
【表】【table】
【表】
比較例 １〜７
例示ジスアゾ顔料(1)(3)(4)に代えて顔料の中心骨
格を[Table] Comparative Examples 1 to 7 In place of the exemplified disazo pigments (1), (3), and (4), the central skeleton of the pigment was
【式】型とした、公開
特許公報昭58−80643記載のアゾ顔料No.１、No.２、
No.３の顔料を用いて比較資料１、２、３を作成し
た。次に例示ジスアゾ顔料(1)、（14）、（19）、（34
）
に代えて、顔料の中心骨格を順に[Formula] Azo pigments No. 1 and No. 2 described in published patent publication No. 58-80643,
Comparative materials 1, 2, and 3 were created using pigment No. 3. Next, exemplified disazo pigments (1), (14), (19), (34
)
Instead of , the central skeleton of the pigment is
【式】【formula】
【式】【formula】
【式】【formula】
【式】
とした比較顔料を用い、比較例４、５、６、７を
作成した。
比較顔料１〜７を用いた比較資料１〜７につい
て、実施例１と同様にして帯電測定を行つた。
第２表に本発明に対比させた比較例の特性を示
す。Comparative Examples 4, 5, 6, and 7 were prepared using the comparative pigments shown in the following formula. Charge measurement was carried out in the same manner as in Example 1 for Comparative Materials 1 to 7 using Comparative Pigments 1 to 7. Table 2 shows the characteristics of comparative examples compared to the present invention.
【表】【table】
【表】
※ 第１表のデータより抜粋
第２表の結果より明らかなように本発明の感光
体は顔料の中心骨格に−NH−基を有しているこ
とと、一つ以上の多環芳香環又はヘテロ環を含ん
でいることにより、電子写真的な感度が著しく良
好になることが確認された。
実施例 41〜46
実施例１、３、４、12、14、25に用いた感光体
を用い繰返し使用時の明部電位と暗部電位の変動
を測定した。方法としては−5.6kVのコロナ帯電
器、露光光学系、現像器、転写帯電器、除電露光
光学系およびクリーナーを備えた電子写真複写機
は、シリンダーに感光体を貼り付けた。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つている。この複写機を用い
て、初期の明部電位（VL）と暗部電位（VD）を
それぞれ100V、−600V付近に設定し、5000回使
用した後の明部電位（VL）暗部電位（VD）を測
定した。この結果を第３表に示す。[Table] * Extracted from the data in Table 1 As is clear from the results in Table 2, the photoreceptor of the present invention has an -NH- group in the central skeleton of the pigment, and one or more polycyclic It was confirmed that electrophotographic sensitivity is significantly improved by containing an aromatic ring or a heterocycle. Examples 41 to 46 Using the photoreceptors used in Examples 1, 3, 4, 12, 14, and 25, fluctuations in bright area potential and dark area potential during repeated use were measured. As for the method, an electrophotographic copying machine equipped with a -5.6 kV corona charger, an exposure optical system, a developer, a transfer charger, a static elimination exposure optical system, and a cleaner was used, and a photoreceptor was attached to a cylinder. This copying machine is configured to produce an image on transfer paper as a cylinder is driven. Using this copying machine, the initial bright area potential (V L ) and dark area potential (V D ) were set to around 100 V and -600 V, respectively, and the bright area potential (V L ) and dark area potential ( V D ) was measured. The results are shown in Table 3.
【表】
実施例 47
実施例１で作成した電荷発生層の上に、２，
４，７−トリニトロ−９−フルオレノン５ｇとポ
リ−４，4′−ジオキシジフエニル−２，2′−プロ
パンカーボネート（分子量（300000）５ｇをテト
ラヒドロフラン70mlに溶解して作成した塗布液を
乾燥後の塗工量が10ｇ／m2となる様に塗布し、乾
燥した。
こうして作成した電子写真感光体を実施例１と
同様の方法で帯電測定を行なつた。この時、帯電
極性はとした。この結果を第４表に示す。
第４表
VD 580ボルト
E1/2：4.0lux.sec
実施例 48
アルミ蒸着ポリエチレンテレフタレートフエル
ムのアルミ面上に膜厚0.5μのポリビニルアルコー
ルの被膜を形成した。
次に、実施例１で用いたジスアゾ顔料の分散液
を先に形成したポリビニルアルコール層の上に、
乾燥後の膜厚が0.5μとなる様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。
次いで、構造式
のピラゾリン化合物５ｇとポリアリレート樹脂
（ビスフエノール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70mlに
溶かした液を電荷発生層の上に乾燥後の膜厚が
10μとなる様に塗布し乾燥して電荷輸送層を形成
した。
こうして調製した感光体の帯電特性および耐久
特性を実施例１及び実施例41と同様の方法によつ
て測定した。この結果を第５表に示す。
第５表
VD：−600V
E1/2：4.3lux.sec
耐久特性
初 期 5000枚耐久性
VD VL VD VL
−600V −100V −620V −125V
第５表の結果より感度もよく、耐久使用時の電
位安定性も良好である。
実施例 49
厚さ100ミクロン厚のアルミ板上にガゼインの
アンモニア水溶液を塗布し、乾燥して膜厚0.5ミ
クロンの下引層を形成した。
次に、２，４，７−トリニトロ−９−フルオレ
ノン５ｇとポリ−Ｎ−ビニルカルバゾール（数平
均分子量300000）５ｇをテトラヒドロフラン70ml
に溶かして電荷移動錯化合物を形成した。この電
荷移動錯化合物と前記例示のジスアゾ顔料No.
（26）１ｇを、ポリエステル樹脂（バイロン：東
洋紡製）５ｇをテトラヒドロフラン70mlに溶かし
た液に加え、分散した。この分散液を下引層の上
に乾燥後の膜厚が12ミクロンとなる様に塗布し、
乾燥した。
こうして調製した感光体の帯電特性と耐久特性
を実施例１と同様の方法によつて測定した。この
結果を第６表に示す。但し、帯電極性はとし
た。
第６表
VD：570V
E1/2：4.7lux.sec
実施例 50
実施例１で用いたガゼイン層を施したアルミ基
板のカゼイン層上に実施例１の電荷構造層、電荷
発生層を順次積層し、層構成を異にする以外は実
施例１と全く同様にして感光体を形成し、実施例
１と同様に帯電測定した。但し帯電極性をとし
た。帯電特性を第７表に示す。
第７表
VD：＋600V
E1/2：4.9lux.sec
実施例 51
アルミニウムシリンダー上にカゼインのアンモ
ニア水溶液（ガゼイン11.2ｇ、28％アンモニア水
１ｇ、水22.2ml）を浸漬コーテイング法で塗工
し、乾燥して塗工量1.0ｇ／m2の下引層を形成し
た。
次に、前述のジスアゾ顔料No.（58）の１重量
部、ブチラール樹脂（エスレツクBM−２：積水
化学(株)製）１重量部とイソプロピルアルコール30
重量部をボールミル分散機で４時間分散した。こ
の分散液を先に形成した下引層の上に浸漬コーテ
イング法で塗工し、乾燥して電荷発生層を形成し
た。この時の膜厚は0.3ミクロンであつた。
次に、実施例１に用いたヒドラゾン化合物１重
量部、ポリスルホン樹脂（P1700：ユニオンカー
バイト社製）、１重量部とモノクロルベンゼン６
重量部を混合し、撹拌機で撹拌溶解した。この液
を電荷発生層の上に浸漬コーテイング法で塗工
し、乾燥して電荷輸送層を形成した。この時の膜
厚は、12ミクロンであつた。
こうして調製した感光体に−5kVのコロナ放電
を行なつた。この時の表面電位を測定した（初期
電位VO）。さらに、この感光体を５秒間暗所で放
置した後の表面電位を測定した（暗減衰VK）。感
度は、暗減衰した後の電位VKを1/2に減衰するに
必要な露光量（E1/2マイクロジユール／cm2）を測
定することによつて評価した。この際、光源とし
てガリウム／アルミニウム／ヒ素の三元系半導体
レーザー（出力：５ｍＷ：発振波長778nｍ）を
用いた。これらの結果は、次のとおりであつた。
VO：−520ボルト
VK：91％
E1/2：1.3マイクロジユール／cm2
次に同上の半導体レーザーを備えた反転現像方
式の電子写真方式プリンターであるレーザービー
ムプリンター（キヤノン製LBP−CX）に上記感
光体をLBP−CXの感光体に置き換えてセツトし
実際の画像形成テストを行つた。条件は以下の通
りである。
一次帯電後の表面電位；−700V、像露光後の
表面電位；−150V（露光量2μJ／cm2）、転写電位；
−700V、現像剤極性；負極性、プロセススピー
ト；50mm／sec、現像条件（現像バイアス）；−
450V、像露光スキヤン方式；イメージスキヤン、
一次帯電前露光；50lux.secの赤色全面露光画像
形成はレーザービームを文字信号及び画像信号に
従つてラインスキヤンして行つたが、文字、画像
共に良好なプリントが得られた。[Table] Example 47 On the charge generation layer prepared in Example 1, 2,
After drying a coating solution prepared by dissolving 5 g of 4,7-trinitro-9-fluorenone and 5 g of poly-4,4'-dioxydiphenyl-2,2'-propane carbonate (molecular weight (300000) in 70 ml of tetrahydrofuran). The coating amount was 10 g/m 2 and dried. The electrophotographic photoreceptor thus prepared was subjected to charge measurement in the same manner as in Example 1. At this time, the charge polarity was The results are shown in Table 4. Table 4 V D 580 Volts E 1/2 : 4.0 lux.sec Example 48 A polyvinyl alcohol film with a thickness of 0.5μ was applied to the aluminum surface of aluminum vapor-deposited polyethylene terephthalate film. Next, the disazo pigment dispersion used in Example 1 was placed on the polyvinyl alcohol layer formed earlier.
It was coated with a Mayer bar so that the film thickness after drying was 0.5μ, and dried to form a charge generation layer. Then, the structural formula A solution prepared by dissolving 5 g of pyrazoline compound and 5 g of polyarylate resin (condensation polymer of bisphenol A and terephthalic acid-isophthalic acid) in 70 ml of tetrahydrofuran was placed on the charge generation layer to determine the film thickness after drying.
It was applied to a thickness of 10μ and dried to form a charge transport layer. The charging characteristics and durability characteristics of the photoreceptor thus prepared were measured in the same manner as in Examples 1 and 41. The results are shown in Table 5. Table 5 V D : -600V E 1/2 : 4.3lux.sec Durability characteristics Initial 5000 sheets durability V D V L V D V L -600V -100V -620V -125V Sensitivity is better than the results in Table 5 The potential stability during long-term use is also good. Example 49 An ammonia aqueous solution of casein was applied onto an aluminum plate with a thickness of 100 microns and dried to form a subbing layer with a thickness of 0.5 microns. Next, 5 g of 2,4,7-trinitro-9-fluorenone and 5 g of poly-N-vinylcarbazole (number average molecular weight 300,000) were added to 70 ml of tetrahydrofuran.
to form a charge transfer complex. This charge transfer complex compound and the above-mentioned disazo pigment No.
(26) 1 g was added to a solution in which 5 g of polyester resin (Vylon, manufactured by Toyobo) was dissolved in 70 ml of tetrahydrofuran, and dispersed. This dispersion was applied onto the undercoat layer so that the film thickness after drying was 12 microns.
Dry. The charging characteristics and durability characteristics of the photoreceptor thus prepared were measured in the same manner as in Example 1. The results are shown in Table 6. However, the charging polarity was determined. Table 6 V D : 570V E 1/2 : 4.7lux.sec Example 50 The charge structure layer and charge generation layer of Example 1 were sequentially applied on the casein layer of the casein layer-coated aluminum substrate used in Example 1. A photoreceptor was formed in the same manner as in Example 1, except that the photoreceptor was laminated and the layer structure was different, and charging was measured in the same manner as in Example 1. However, the charging polarity was determined. Charging characteristics are shown in Table 7. Table 7 V D : +600V E 1/2 : 4.9lux.sec Example 51 An ammonia aqueous solution of casein (11.2 g of casein, 1 g of 28% ammonia water, 22.2 ml of water) was coated on an aluminum cylinder by dip coating. , and dried to form a subbing layer with a coating weight of 1.0 g/m 2 . Next, 1 part by weight of the above-mentioned disazo pigment No. (58), 1 part by weight of butyral resin (Eslec BM-2: manufactured by Sekisui Chemical Co., Ltd.) and 30 parts by weight of isopropyl alcohol.
Parts by weight were dispersed for 4 hours using a ball mill disperser. This dispersion was applied onto the previously formed subbing layer by a dip coating method and dried to form a charge generation layer. The film thickness at this time was 0.3 microns. Next, 1 part by weight of the hydrazone compound used in Example 1, 1 part by weight of polysulfone resin (P1700: manufactured by Union Carbide) and 6 parts by weight of monochlorobenzene were added.
Parts by weight were mixed and dissolved by stirring with a stirrer. This liquid was applied onto the charge generation layer by dip coating and dried to form a charge transport layer. The film thickness at this time was 12 microns. A -5 kV corona discharge was applied to the photoreceptor thus prepared. The surface potential at this time was measured (initial potential VO ). Furthermore, the surface potential of this photoreceptor was measured after it was left in a dark place for 5 seconds (dark decay V K ). Sensitivity was evaluated by measuring the exposure amount (E 1/2 microjoule/cm 2 ) required to attenuate the potential V K by 1/2 after dark decay. At this time, a gallium/aluminum/arsenic ternary semiconductor laser (output: 5 mW, oscillation wavelength 778 nm) was used as a light source. These results were as follows. V O : -520 volts V K : 91% E 1/2 : 1.3 microjoules/cm Second , a laser beam printer (Canon's LBP- An actual image forming test was conducted by replacing the above photoreceptor with an LBP-CX photoreceptor. The conditions are as follows. Surface potential after primary charging: -700V, surface potential after image exposure: -150V (exposure amount: 2 μJ/cm 2 ), transfer potential:
-700V, developer polarity: negative polarity, process speed: 50mm/sec, development conditions (development bias): -
450V, image exposure scan method; image scan,
Primary pre-charging exposure: 50 lux.sec full red exposure Image formation was performed by line scanning a laser beam in accordance with character and image signals, and good prints were obtained for both characters and images.
Claims (1)
るジスアゾ顔料を含有する感光層を有することを
特徴とする電子写真感光体。 一般式〔〕 Ａ−Ｎ＝Ｎ−Ar1−NH−Ar2−Ｎ＝Ｎ−Ａ
〔〕 （式中、Ａはフエノール性OH基を有するカプラ
ー残基を表す。Ar1及びAr2は、それぞれ、置換
基を有してもよいフエニレン基、置換基を有して
もよいビフエニレン基もしくは縮合多環芳香族基
又は２価の複素環基を表す。但し、Ar1及びAr2
が、共に置換基を有していてもよいフエニレン基
であることはない。） ２ 一般式〔〕のＡが、下記一般式〔〕で示
されるもの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〔〕 （式中、Ｘはベンゼン環と縮合して、置換基を有
していてもよい多環芳香族環又はヘテロ環を形成
するのに必要な残基を表す。R1及びR2は、それ
ぞれ水素原子、置換基を有していてもよいアルキ
ル基、アラルキル基、アリール基、又はヘテロ環
基を表すか、あるいはR1とR2とで、結合する窒
素原子と共に環状アミノ基を形成するのに必要な
残基を表す。） ３ R1が水素であり、R2が下記一般式［］で
示されるフエニル基である特許請求の範囲第２項
記載の電子写真感光体。 一般式［］ （式中、R3は、ハロゲン原子、ニトロ基、シア
ノ基、又はトリフルオロメチル基を表す。） ４ Ａが下記一般式〔〕で示されるものである
特許請求の範囲第２項記載の電子写真感光体。 一般式〔〕 （式中、R4は置換基を有していてもよいフエニ
ル基を表す。） ５ 一般式〔〕のＡが、下記一般式〔〕で示
されるもの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〔〕 （式中、R5は置換基を有していてもよいアルキ
ル基、アラルキル基又はアリール基を表す。） ６ 一般式〔〕のＡが、下記一般式〔〕で示
されるもの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〔〕 （式中、R6は置換基を有してもよいアルキル基、
アラルキル基又はアリール基を表す。） ７ 一般式〔〕のＡが、下記一般式［］で示
されるもの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［］ （式中、Y1は２つの窒素原子と結合した２価の
芳香族炭化水素を表すか、あるいは、
【式】により２価のヘテロ環基を形成す るのに必要な残基を表す。） ８ 一般式〔〕のＡが、下記一般式［］で示
されるもの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［］ （式中、Y2は２つの窒素原子と結合した２価の
芳香族炭化水素を表すか、あるいは、
【式】により２価のヘテロ環基を形成す るのに必要な残基を表す。） ９ 一般式〔〕のＡが、下記一般式〔〕で示
されるもの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〔〕 （式中、Z1はベンゼン環と縮合して、置換基を有
していてもよい多環芳香族環又はヘテロ環を形成
するのに必要な残基を表す。R7及びR8は、それ
ぞれ、水素原子、置換基されていてもよいアリー
ル基又はヘテロ環基を表すか、あるいは、R7と
R8とが結合する炭素原子と共に５員環又は員環
を形成するのに必要な残基を表し、これら５員環
又は６員環は縮合芳香族環を有していてもよい。） １０ 一般式〔〕のＡが、下記一般式〔〕で
示されるもの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〔〕 （式中、Z2はベンゼン環と縮合して、置換基を有
していてもよい多環芳香族環又はヘテロ環を形成
するのに必要な残基を表す。R9及びR10は、それ
ぞれ、水素原子、置換されていてもよいアリール
基又はヘテロ環基を表す。） １１ 感光層が、一般式〔〕で示されるジスア
ゾ顔料の少なくとも１種を含有する電荷発生層
と、電荷輸送層とを構成成分とする積層構造のも
のである特許請求の範囲第１項記載の電子写真感
光体。[Scope of Claims] 1. An electrophotographic photoreceptor comprising a photosensitive layer containing a disazo pigment represented by the following general formula [] on a conductive substrate. General formula [] A-N=N-Ar 1 -NH-Ar 2 -N=N-A
[] (In the formula, A represents a coupler residue having a phenolic OH group. Ar 1 and Ar 2 are a phenylene group which may have a substituent, and a biphenylene group which may have a substituent, respectively) or represents a fused polycyclic aromatic group or a divalent heterocyclic group.However, Ar 1 and Ar 2
However, neither of them is a phenylene group which may have a substituent. ) 2. The electrophotographic photoreceptor according to claim 1, wherein A in the general formula [] is represented by the following general formula []. General formula [] ( wherein , It represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, or a heterocyclic group which may have a substituent, or R 1 and R 2 together with the nitrogen atom bonded form a cyclic amino group. 3. The electrophotographic photoreceptor according to claim 2, wherein R 1 is hydrogen and R 2 is a phenyl group represented by the following general formula []. General formula [] (In the formula, R 3 represents a halogen atom, a nitro group, a cyano group, or a trifluoromethyl group.) 4 The electron according to claim 2, wherein A is represented by the following general formula [] Photographic photoreceptor. General formula [] (In the formula, R 4 represents a phenyl group which may have a substituent.) 5. Claim 1, wherein A in the general formula [] is represented by the following general formula [] electrophotographic photoreceptor. General formula [] (In the formula, R 5 represents an alkyl group, an aralkyl group, or an aryl group that may have a substituent.) 6. A patent claim in which A in the general formula [] is represented by the following general formula [] The electrophotographic photoreceptor according to item 1. General formula [] (In the formula, R 6 is an alkyl group that may have a substituent,
Represents an aralkyl group or an aryl group. ) 7 The electrophotographic photoreceptor according to claim 1, wherein A in the general formula [] is represented by the following general formula []. General formula [] (In the formula, Y 1 represents a divalent aromatic hydrocarbon bonded to two nitrogen atoms, or
[Formula] represents a residue necessary to form a divalent heterocyclic group. ) 8 The electrophotographic photoreceptor according to claim 1, wherein A in the general formula [] is represented by the following general formula []. General formula [] (In the formula, Y 2 represents a divalent aromatic hydrocarbon bonded to two nitrogen atoms, or
[Formula] represents a residue necessary to form a divalent heterocyclic group. ) 9 The electrophotographic photoreceptor according to claim 1, wherein A in the general formula [] is represented by the following general formula []. General formula [] (In the formula, Z 1 represents a residue necessary to form a polycyclic aromatic ring or a heterocycle which may have a substituent by condensing with a benzene ring. R 7 and R 8 are Each represents a hydrogen atom, an optionally substituted aryl group, or a heterocyclic group, or R 7 and
It represents a residue necessary to form a 5-membered ring or a membered ring together with the carbon atom to which R 8 is bonded, and these 5-membered or 6-membered rings may have a fused aromatic ring. ) 10 The electrophotographic photoreceptor according to claim 1, wherein A in the general formula [] is represented by the following general formula []. General formula [] (In the formula, Z 2 represents a residue necessary to form a polycyclic aromatic ring or a heterocycle which may have a substituent by condensing with a benzene ring. R 9 and R 10 are Each represents a hydrogen atom, an optionally substituted aryl group, or a heterocyclic group.) 11. A charge generation layer in which the photosensitive layer contains at least one disazo pigment represented by the general formula [], and a charge transport layer. The electrophotographic photoreceptor according to claim 1, which has a laminated structure comprising:
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11911685A JPS61275850A (en) | 1985-05-31 | 1985-05-31 | Electrophotographic sensitive body |
| US06/865,849 US4702982A (en) | 1985-05-31 | 1986-05-22 | Electrophotographic photosensitive member comprising disazo pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11911685A JPS61275850A (en) | 1985-05-31 | 1985-05-31 | Electrophotographic sensitive body |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61275850A JPS61275850A (en) | 1986-12-05 |
| JPH0417426B2 true JPH0417426B2 (en) | 1992-03-25 |
Family
ID=14753324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11911685A Granted JPS61275850A (en) | 1985-05-31 | 1985-05-31 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61275850A (en) |
-
1985
- 1985-05-31 JP JP11911685A patent/JPS61275850A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61275850A (en) | 1986-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |