JPH0547102B2 - - Google Patents
Info
- Publication number
- JPH0547102B2 JPH0547102B2 JP60218054A JP21805485A JPH0547102B2 JP H0547102 B2 JPH0547102 B2 JP H0547102B2 JP 60218054 A JP60218054 A JP 60218054A JP 21805485 A JP21805485 A JP 21805485A JP H0547102 B2 JPH0547102 B2 JP H0547102B2
- Authority
- JP
- Japan
- Prior art keywords
- ring
- group
- general formula
- resin
- formula
- 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 - Lifetime
Links
- 239000000049 pigment Substances 0.000 claims description 51
- 229920005989 resin Polymers 0.000 claims description 39
- 239000011347 resin Substances 0.000 claims description 39
- 108091008695 photoreceptors Proteins 0.000 claims description 31
- 229920000515 polycarbonate Polymers 0.000 claims description 28
- 239000004417 polycarbonate Substances 0.000 claims description 28
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000005577 anthracene group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims 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 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000003367 polycyclic group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical group C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- NYESPUIMUJRIAP-UHFFFAOYSA-N naphtho[1,2-e][1]benzofuran Chemical group C1=CC=CC2=C3C(C=CO4)=C4C=CC3=CC=C21 NYESPUIMUJRIAP-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- -1 methoxy, ethoxy, propoxy, butoxy Chemical group 0.000 description 29
- 230000032258 transport Effects 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 12
- 230000035945 sensitivity Effects 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 10
- 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 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
- 238000000034 method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 239000012860 organic pigment 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-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
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000006185 dispersion Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 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
- 230000004888 barrier function Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical group C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 229940097275 indigo Drugs 0.000 description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Chemical class 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- JBDYKGMNMDIHFL-UHFFFAOYSA-N 1-nitroanthracene Chemical compound C1=CC=C2C=C3C([N+](=O)[O-])=CC=CC3=CC2=C1 JBDYKGMNMDIHFL-UHFFFAOYSA-N 0.000 description 1
- JFSIHROQZLYJMY-UHFFFAOYSA-N 2,2-dinitro-1-phenylethanone Chemical compound [O-][N+](=O)C([N+]([O-])=O)C(=O)C1=CC=CC=C1 JFSIHROQZLYJMY-UHFFFAOYSA-N 0.000 description 1
- FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-UHFFFAOYSA-N 0.000 description 1
- JWWQNDLIYXEFQL-UHFFFAOYSA-N 2,3-dinitrofluoren-1-one Chemical compound C1=CC=C2C3=CC([N+](=O)[O-])=C([N+]([O-])=O)C(=O)C3=CC2=C1 JWWQNDLIYXEFQL-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
- FLCWJWNCSHIREG-UHFFFAOYSA-N 2-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=CC=C1C=O FLCWJWNCSHIREG-UHFFFAOYSA-N 0.000 description 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
- FMXDVBRYDYFVGS-UHFFFAOYSA-N 2-methoxy-1,3,5-trinitrobenzene Chemical compound COC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O FMXDVBRYDYFVGS-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
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- YFPSDOXLHBDCOR-UHFFFAOYSA-N Pyrene-1,6-dione Chemical compound C1=CC(C(=O)C=C2)=C3C2=CC=C2C(=O)C=CC1=C32 YFPSDOXLHBDCOR-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- MZZSDCJQCLYLLL-UHFFFAOYSA-N Secalonsaeure A Natural products COC(=O)C12OC3C(CC1=C(O)CC(C)C2O)C(=CC=C3c4ccc(O)c5C(=O)C6=C(O)CC(C)C(O)C6(Oc45)C(=O)OC)O MZZSDCJQCLYLLL-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Chemical class 0.000 description 1
- UATJOMSPNYCXIX-UHFFFAOYSA-N Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920000609 methyl cellulose Chemical class 0.000 description 1
- 239000001923 methylcellulose Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C=C4NC(=NC4=CC=3)C=3C=CC(O)=CC=3)C2=C1 INAAIJLSXJJHOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Chemical class 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- QNFCBQVDIQELAS-UHFFFAOYSA-N quinoline;cyanide Chemical compound N#[C-].N1=CC=CC2=CC=CC=C21 QNFCBQVDIQELAS-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 238000012360 testing method Methods 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
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0564—Polycarbonates
-
- 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
- G03G5/0679—Disazo dyes
Description
[産業上の利用分野]
本発明は電子写真感光体に関し、特に特定のジ
スアゾ顔料とポリカーボネートZ樹脂を含有する
ことにより、特性の改良された感光層を有する電
子写真感光体に関する。
[従来の技術]
従来の電子写真感光体としては、無機光導電物
質のセレン、硫化カドミユウム、酸化亜鉛や非晶
質硅素を用いたものや、ポリ−N−ビニルカルバ
ゾール、ポリビニルアントラセン等の光導電性ポ
リマー、又は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の如き低分子の各
種有機光導電物質を用いたものや有機顔料を分散
したものが知られている。このうち、電子写真感
光体に使用される有機顔料としては、スーダンレ
ツド、ダイアンブルー等のアゾ顔料、ジスアゾ顔
料、アルゴールイエロー、ピレンキノン等のキノ
ン顔料、キノシアニン顔料、ペリレン顔料、イン
ジゴ、チオインジゴ等のインジゴ顔料、インドフ
アーストオレンジトナー等のビスベンゾイミミダ
ゾール顔料、銅フタロシアニン等のフタロシアニ
ン顔料、キナクリドン顔料等が挙げられる。
これらの顔料を分散して有する感光体は一部実
用化されているものもあるが感度的に充分満足さ
れているものではない。
これは顔料の場合は成膜されるための結着剤と
いうものが必要であり、この結着剤によつて電荷
の移動が阻害されるためである。
そのため顔料を使用する場合には、その顔料に
とつて最適な結着剤が不可欠である。
一方、感光層を光によつて電荷を発生する電荷
発生層とその電荷を輸送する電荷輸送層に分けた
機能分離型感光層の場合においては顔料は電荷発
生層に使用される。この場合には、電荷発生層の
結着剤は勿論、電荷輸送層の結着剤も感度を決定
する要因となる。
即ち、電荷発生層で発生した電荷を効率よく電
荷輸送層に注入させることが高感度化の決め手で
あるが電荷発生層の顔料と電荷輸送層の結着剤の
組み合わせが悪いと両層の界面に注入の障壁がで
き注入効率が低下する。そのため機能分離型感光
層においても顔料にとつて最適な電荷輸送層の結
着剤の選定が不可欠である。
[発明が解決しようとする問題点]
本発明は、上記のような従来の技術に鑑み、感
光層中に含まれる顔料と結着剤樹脂を組み合わせ
ることにより、より高感度な電子写真感光体を提
供することを目的とする。
さらに他の目的は生産安定性に優れた電子写真
感光体を提供することである。
[問題点を解決するための手段、作用]
本発明は顔料として後記一般式(1)で示されるジ
スアゾ顔料の少なくとも1種を用い、結着剤とし
て後記一般式(2)で示されるポリカーボネートZ樹
脂とを組み合わせることにより前記目的を達成し
たものである。
即ち、本発明は下記一般式(1)で示されるジスア
ゾ顔料の少なくとも1種と下記一般式(2)で示され
るポリカーボネートZ樹脂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から構成さ
れる。
一般式
式中、Aはフエノール性OH基を有するカツプ
ラー残基を示し、R1、R1′、R2及びR2′は水素原
子、ハロゲン原子又は置換基を有してもよいアル
キル基、アルコキシ基及びアラルキル基から選ば
れる基を示す。
一般式
式中、nは平均重合度を示し、50〜5000の範囲
である。
本発明によれば、一般式(1)で示されるジスアゾ
顔料は、他の有機顔料に比べて高感度で光照射に
よる劣化も小さく高耐久である。
さらに一般式(2)で示されるポリカーボネートZ
樹脂と組み合わせることにより、高感度で機械的
な表面劣化の少ない高耐久の感光層が形成され
る。
上記一般式(1)におけるR1、R1′、R2及びR2′の
示す基において、ハロゲン原子の具体例としては
フツ素原子、塩素原子、臭素原子、ヨウ素原子等
が挙げられ、アルキル基の具体例としてはメチ
ル、エチル、プロピル、ブチル等の基、アルコキ
シ基の具体例としてはメトキシ、エトキシ、プロ
ポキシ、ブトキシ等の基、アラルキル基の具体例
としてはベンジル、フエネチル、ナフチルメチル
等の基が挙げられる。
さらに上記アルキル基、アルコキシ基及びアラ
ルキル基の有してもよい置換基としては、例えば
メチル、エチル、プロピル等のアルキル基、メト
キシ、エトキシ、プロポキシ等のアルコキシ基、
フツ素原子、塩素原子、臭素原子、ヨウ素原子等
のハロゲン原子、ニトロ基、シアノ基、ジメチル
アミノ、ジベンジルアミノ、ジフエニルアミノ等
の置換アミノ基等が挙げられる。
又、上記一般式(1)におけるAで示されるフエノ
ール性OH基を有するカツプラー残基としては、
下記一般式(3)乃至(9)で示される基から選ばれる。
一般式
式中、Xはベンゼン環と縮合してなるナフタレ
ン環、アントラセン環、カルバゾール環、ベンズ
カルバゾール環、ジベンゾフラン環、ベンゾナフ
トフラン環及びジフエニレンサルフアイド環から
選ばれる多環芳香環又はヘテロ環を形成するに必
要な残基を示し、なかでもナフタレン環、アント
ラセン環、ベンズカルバゾール環、カルバゾール
環がより望ましい。R3及びR4は水素原子、置換
基を有してもよいアルキル基、アラルキル基、ア
リール基及びヘテロ環基から選ばれる基、又は
R3、R4の結合する窒素原子とともに形成する環
状アミノ基を示し、アルキル基の具体例としては
メチル、エチル、プロピル、ブチル等の基が挙げ
られ、アラルキル基の具体例としてはベンジル、
フエネチル、ナフチルメチル等の基が挙げられ、
アリール基の具体例としてはフエニル、ジフエニ
ル、ナフチル、アンスリル等の基が挙げられ、ヘ
テロ環基としてはカルバゾール、ジベンゾフラ
ン、ベンズイミダゾロン、ベンズチアゾール、チ
アゾール、ピリジン等の基が挙げられる。
上記アルキル基、アラルキル基、アリール基及
びヘテロ環基の有してもよい置換基としては、例
えばメチル、エチル、プロピル等のアルキル基、
メトキシ、エトキシ、プロポキシ等のアルコキシ
基、フツ素原子、塩素原子、臭素原子、ヨウ素原
子等のハロゲン原子、ニトロ基、シアノ基、ジメ
チルアミノ、ジベンジルアミノ、ジフエニルアミ
ノ等の置換アミノ基等が挙げられる。
一般式
一般式
一般式(4)、(5)中のR5及びR6は置換基を有して
もよいアルキル基、アラルキル基及びアリール基
から選ばれる基を示す。
上記R5及びR6の具体例としては、前記一般式
(3)におけるR3及びR4と同じ例が挙げられる。
一般式
一般式
一般式(6)及び(7)中のYは芳香族炭化水素の2価
の基又は窒素原子を環内に含むヘテロ環の2価の
基を示す。
上記芳香族炭化水素の2価の基としては、0−
フエニレン等の単環式芳香族炭化水素の2価の
基、0−ナフチレン、ペリナフチレン、1,2−
アンスリレン、9,10−フエナンスリレン等の多
環式芳香族炭化水素の2価の基が挙げられ、窒素
原子を環内に含むヘテロ環の2価の基としては、
例えば3,4−ピラゾールジイル、2,3−ピリ
ジンジイル、4,5−ピリミジンジイル、6,7
−イミダゾールジイル、5,6−ベンズイミダゾ
ールジイル、6,7−キノリンジイル等の5員あ
るいは6員環のヘテロ環で2価の基等が挙げられ
る。
一般式
式中、R7及びR8は水素原子、置換基を有して
もよいアルキル基、アラルキル基、アリール基及
びヘテロ環基から選ばれる基、又はR7、R8の結
合する炭素原子とともに5員あるいは6員環を形
成する残基を示し、この5員あるいは6員環は縮
合芳香族環を有してもよく、Zはベンゼン環と縮
合してなるナフタレン環、アントラセン環、カル
バゾール環、ベンズカルバゾール環、ジベンゾフ
ラン環、ベンゾナフトフラン環及びジフエニレン
サルフアイド環から選ばれる多環芳香環、又はヘ
テロ環を形成するに必要な残基を示す。
上記アルキル基の具体例としてはメチル、エチ
ル、プロピル、ブチル等の基、アラルキル基の具
体例としてはベンジル、フエネチル、ナフチルメ
チル等の基、アリール基の具体例としてはフエニ
ル、ナフチル、アンスリル、ピレニル等の基が挙
げられ、ヘテロ環基の具体例としてはピリジル、
チエニル、フリル、カルバゾイル等の基が挙げら
れ、さらに、上記基の有してもよい置換基として
は、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、エチル、プロピ
ル、ブチル等のアルキル基、メトキシ、エトキ
シ、プロボキシ、ブトキシ等のアルコキシ基、ニ
トロ基、シアノ基、ジメチルアミノ、ジエチルア
ミノ、ジプロピルアミノ、ジベンジルアミノ、ジ
フエニルアミノ、モルホリノ、ピペリジノ、ピロ
リジノ等の置換アミノ基等が挙げられる。上記
R7、R8の結合炭素原子とともに5員あるいは6
員環を形成する残基であつて、この5員あるいは
6員環は縮合芳香族環を有してもよい基の具体例
としてはシクロペンチリデン、シクロヘキシリデ
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
もよいアルキル基、アラルキル基、アリール基及
びヘテロ環基から選ばれる基、又はR9、R10の結
合する炭素原子とともに5員あるいは6員環を形
成する残基を示し、この5員あるいは6員環は縮
合芳香族環を有してもよく、Zはベンゼン環と縮
合してなるナフタレン環、アントラセン環、カル
バゾール環、ベンズカルバゾール環、ジベンゾフ
ラン環、ベンゾナフトフラン環及びジフエニレン
サルフアイド環から選ばれる多環芳香環、又はヘ
テロ環を形成するに必要な残基を示す。
上記基のアルキル基の具体例としてはメチル、
エチル、プロピル、ブチル等の基、アラルキル基
の具体例としてはベンジル、フエネチル、ナフチ
ルメチル等の基、アリール基の具体例としてはフ
エニル、ジフエニル、ナフチル、アンスリル、ピ
レニル等の基、ヘテロ環基の具体例としてはピリ
ジル、チエニル、フリル、カルバゾイル等の基が
挙げられ、さらに上記基が有してもよい置換基と
しては、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、エチル、プロ
ピル、ブチル等のアルキル基、メトキシ、エトキ
シ、プロポキシ、ブトキシ等のアルコキシ基、ニ
トロ基、シアノ基、ジメチルアミノ、ジエチルア
ミノ、ジプロピルアミノ、ジベンジルアミノ、ジ
フエニルアミノ、モルホリノ、ピペリジノ、ピロ
リジノ等の置換アミノ基等が挙げられる。
上記R9、R10の結合炭素原子とともに5員ある
いは6員環を形成する残基であつて、この5員あ
るいは6員環は縮合芳香族環を有してもよい基の
具体例としてはシクロペンチンチリデン、シクロ
ヘキシリデン、9−キサンテニリデン等の基が挙
げられる。
前記一般式(1)で示されるジスアゾ顔料の具体例
を以下に示す。
これらの例示顔料以外にも一般式(1)に含まれる
ジスアゾ顔料は数多く存在する。
前記一般式(2)で示されるポリカーボネートZ樹
脂は、(a)透明性が良好、(b)電気絶縁性、耐電圧が
ともに高い、(c)表面が硬く適度の滑性を有してお
り、機械的に摩耗しにくい等の特徴があり、さら
に(d)溶剤に溶解させた場合の安定性に優れてい
る。
通常のポリカーボネート樹脂、即ち、
なる構造式で示されるビスフエノールA型ポリカ
ーボネート樹脂は高分子の結晶性が高いため溶解
をした場合にゲル化しやすく、2日程度で使用不
可能となる欠点を有しており、この点で大きく異
なる。
本発明の特定のジスアゾ顔料とポリカーボネー
トZ樹脂を組み合わせることにより、顔料粒子と
樹脂の界面に光照射時の電荷の移動を阻止する障
壁層が形成される程度はポリカーボネートZ樹脂
以外との組み合わせより格段に小さく、かつ、ポ
リカーボネートZ樹脂構造式のベンゼン環及びシ
クロヘキシル団が電荷の移動を容易にし、感度を
向上するようである。
本発明による電子写真感光体の形態としては、
(a) 一般式(1)で示されるジスアゾ顔料(以下「ジ
スアゾ顔料」と記載する)をポリカーボネート
Z樹脂に分散した感光層、
(b) ジスアゾ顔料をポリカーボネートZ樹脂と電
荷輸送物質(電子供与性化合物及び/又は電子
受容性化合物)に分散した感光層、
(c) ジスアゾ顔料を結着剤樹脂(ポリカーボネー
トZ樹脂でもよいし、他の樹脂でもよい)に分
散した層を電荷発生層とし、この上にポリカー
ボネートZ樹脂と電荷輸送物質を含む電荷輸送
層を積層した機能分離型感光層、
(d) 電荷輸送層の上にジスアゾ顔料とポリカーボ
ネートZ樹脂を含む電荷発生層を積層した機能
分離型感光層等が挙げられる。
電子供与性化合物としては、主鎖又は側鎖にア
ントラセン、ピレン、フエナンスレン、コロネン
等の多環芳香環又はインドール、カルバゾール、
オキサゾール、イソオキサゾール、チアゾール、
イミダゾール、ピラゾール、オキサジアゾール、
ピラゾリン、チアジアゾール、トリアゾール等の
含窒素ヘテロ環を有する化合物、ヒドラゾン化合
物、芳香族アミノ化合物等が挙げられる。
電子受容性化合物としては、ニトロ基、ニトロ
ソ基、シアノ基等の電子受容性置換基を有する脂
肪族環式化合物、芳香族化合物、ヘテロ環式化合
物等があり、例えばテトラシアノエチレン、トリ
ニトロベンゼン、ジニトロアセトフエノン、トリ
ニトロアニソール、テトラニトロナフタレン、テ
レフタロニトリル、イソフタロニトリル、シアン
化ベンゾイル、シアン化キノリン、シアノピリジ
ン、ニトロアンスラセン、ジニトロフルオレノ
ン、トリニトロフルオレノン、テトラニトロフル
オレノン、テトラシアノピレン等が挙げられる。
電子受容性化合物は一般的に発癌性等の有害性
のため好ましくない。
電子供与性化合物を用いる場合、前述の(c)形態
では負帯電、(d)の形態では正帯電に使用される。
電荷輸送層は、電荷輸送物質と樹脂を5:1〜
1:2(重量比)程度に混合されて形成され、膜
厚は5〜20μ程度である。
前述(c)の形態でジスアゾ顔料の結着剤樹脂とし
ては、ポリカーボネートZのほかポリエステル、
ポリビニルベンザール、ポリビニルブチラール、
ポリビニルピロリドン、メチルセルロース、ポリ
アクリル酸エステル類、セルロースエステル類等
が適宜使用される。
分散は樹脂溶液に顔料を混合した後ボールミ
ル、ロールミル、サンドミル、コロイドミル等の
常法によることができる。
電荷発生層の厚さは0.01〜1μ、好ましくは0.05
〜0.5μである。
電荷輸送層の上に形成される場合には、より厚
く、0.5〜5μ程度である、
顔料と樹脂の比は5:1〜1:2程度である。
[発明の効果]
本発明の電子写真感光体において、特定のジス
アゾ顔料とポリカーボネートZ樹脂を含有する感
光層は高感度で残留電位が少なく、さらに帯電、
露光を繰り返した際の明部電位が上昇することな
く安定しており、又、表面にポリカーボネートZ
樹脂が存在するので表面の高度が高く、潤滑性に
も優れているので摺擦傷が付きにくく、機械的耐
久性を向上させることができる。
さらにポリカーボネートZ樹脂の溶液は保存安
定性が良いので、生産性が向上し、品質安定化に
も貢献することができる。
[実施例]
実施例 1〜6
基体として肉厚0.5mmで60φ×260mmのアルミニ
ウムシリンダーを用意した。
次に共重合ナイロン(商品名CM8000、東レ(株)
製)4部及びタイプ8ナイロン(商品名ラツカマ
イド5003、大日本インキ化学(株)製)4部をメタノ
ール50部、n−ブタノール50部に溶解し、上記基
体上に浸漬塗布して0.6μ厚のポリアミド下引層を
形成した。
次に前記一般式(1)のジスアゾ顔料の例示顔料か
ら選らばれたジスアゾ顔料を10部及びポリビニル
ブチラール(商品名エスレツクBM−2、積水化
学(株)製)10部をシクロヘキサノン120部と共にサ
ンドミル装置で10時間分散した。分散液にメチル
エチルケトン30部を加えて上記下引層上に塗布
し、0.15μ厚の電荷発生層を形成した。
次にポリカーボネートZ樹脂(三菱ガス化学(株)
製)の重量平均分子量12万のもの10部を用意し、
下記構造式のヒドラゾン化合物10部と共に、
モノクロルベンゼン80部に溶解した。これを上記
電荷発生層上に塗布して16μ厚の電荷輸送層を形
成した。
上記選択の例示ジスアゾ顔料(1)、(9)、(14)、(16)、
(22)、(30)に対応して実施例1〜6の電子写真
感光体とする。
このようにして作成した電子写真感光体を、−
5.6KVコロナ帯電、画像露光、乾式トナー現像、
普通紙へのトナー転写、ウレタンゴムブレード
(高度70゜、圧力5Kgw/cm2、感光体に対する角度
20゜)によるクリーニング工程等を有する電子写
真複写機に取り付けて電子写真特性を評価した。
電位を測定すると暗部電位(VD)が−700Vで
10ルツクス・秒の露光を与えた時の電位(VL)
は第1表に示す結果となつた。
比較例 1〜4
実施例1のジスアゾ顔料に代えて下記A〜Dの
有機顔料を用いた他は実施例1と同様な方法で電
子写真感光体を作成した(A〜Dに対応して比較
例1〜4とする)。
電子写真特性の測定結果は第1表に示した。
有機顔料
A β型銅フタロシアニン(大日本インキ化学(株)
製、但し、水、エタノール、メチルエチルケト
ンで順次熱濾過して生成した顔料である)
[Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor, and particularly to an electrophotographic photoreceptor having a photosensitive layer with improved characteristics by containing a specific disazo pigment and a polycarbonate Z resin. [Prior Art] Conventional electrophotographic photoreceptors include those using inorganic photoconductive materials such as selenium, cadmium sulfide, zinc oxide, and amorphous silicon, and those using photoconductive materials such as poly-N-vinylcarbazole and polyvinylanthracene. polymer, or diethylaminobenzaldehyde
Those using various low-molecular organic photoconductive substances such as N,N-diphenylhydrazone and those in which organic pigments are dispersed are known. Among these, organic pigments used in electrophotographic photoreceptors include azo pigments such as Sudan Red and Diane Blue, disazo pigments, quinone pigments such as Algol Yellow and pyrene quinone, quinocyanine pigments, perylene pigments, and indigo pigments such as indigo and thioindigo. , bisbenzimidazole pigments such as India First Orange Toner, phthalocyanine pigments such as copper phthalocyanine, and quinacridone pigments. Although some photoreceptors having these pigments dispersed therein have been put to practical use, they are not fully satisfactory in terms of sensitivity. This is because pigments require a binder to form a film, and this binder inhibits the movement of charges. Therefore, when using pigments, it is essential to use a binder that is optimal for the pigments. On the other hand, in the case of a functionally separated photosensitive layer in which the photosensitive layer is divided into a charge generation layer that generates charges by light and a charge transport layer that transports the charges, a pigment is used in the charge generation layer. In this case, not only the binder of the charge generation layer but also the binder of the charge transport layer becomes a factor in determining the sensitivity. In other words, the key to high sensitivity is to efficiently inject the charges generated in the charge generation layer into the charge transport layer, but if the combination of the pigment in the charge generation layer and the binder in the charge transport layer is poor, the interface between the two layers This creates an injection barrier and reduces injection efficiency. Therefore, even in the functionally separated photosensitive layer, it is essential to select a binder for the charge transport layer that is optimal for the pigment. [Problems to be Solved by the Invention] In view of the above-mentioned conventional techniques, the present invention aims to create an electrophotographic photoreceptor with higher sensitivity by combining a pigment contained in a photosensitive layer and a binder resin. The purpose is to provide. Still another object is to provide an electrophotographic photoreceptor with excellent production stability. [Means and effects for solving the problems] The present invention uses at least one disazo pigment represented by the general formula (1) below as a pigment, and polycarbonate Z represented by the general formula (2) below as a binder. The above object is achieved by combining the resin with the resin. That is, the present invention relates to an electrophotographic photoreceptor having a photosensitive layer containing at least one disazo pigment represented by the following general formula (1) and a polycarbonate Z resin represented by the following general formula (2). configured. general formula In the formula, A represents a coupler residue having a phenolic OH group, and R 1 , R 1 ′, R 2 and R 2 ′ are a hydrogen atom, a halogen atom, or an alkyl group or alkoxy group which may have a substituent. and an aralkyl group. general formula In the formula, n represents the average degree of polymerization and is in the range of 50 to 5000. According to the present invention, the disazo pigment represented by the general formula (1) has higher sensitivity and less deterioration due to light irradiation than other organic pigments, and is highly durable. Furthermore, polycarbonate Z represented by general formula (2)
By combining it with a resin, a highly durable photosensitive layer with high sensitivity and little mechanical surface deterioration is formed. In the groups represented by R 1 , R 1 ', R 2 and R 2 ' in the above general formula (1), specific examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. Specific examples of groups include methyl, ethyl, propyl, butyl, etc. Specific examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, etc. Specific examples of aralkyl groups include benzyl, phenethyl, naphthylmethyl, etc. Examples include groups. Furthermore, the substituents that the alkyl, alkoxy, and aralkyl groups may have include, for example, alkyl groups such as methyl, ethyl, and propyl; alkoxy groups such as methoxy, ethoxy, and propoxy;
Examples include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom, and substituted amino groups such as nitro group, cyano group, dimethylamino, dibenzylamino, and diphenylamino. In addition, the coupler residue having a phenolic OH group represented by A in the above general formula (1) is:
It is selected from the groups represented by the following general formulas (3) to (9). general formula In the formula, Residues necessary for formation are shown, and among them, naphthalene ring, anthracene ring, benzcarbazole ring, and carbazole ring are more preferable. R 3 and R 4 are a hydrogen atom, a group selected from an alkyl group that may have a substituent, an aralkyl group, an aryl group, and a heterocyclic group, or
Indicates a cyclic amino group formed with the nitrogen atom to which R 3 and R 4 are bonded. Specific examples of the alkyl group include methyl, ethyl, propyl, butyl, etc. Specific examples of the aralkyl group include benzyl,
Examples include groups such as phenethyl and naphthylmethyl;
Specific examples of the aryl group include phenyl, diphenyl, naphthyl, and anthryl, and examples of the heterocyclic group include carbazole, dibenzofuran, benzimidazolone, benzthiazole, thiazole, and pyridine. Examples of the substituents that the alkyl group, aralkyl group, aryl group, and heterocyclic group may have include alkyl groups such as methyl, ethyl, and propyl;
Examples include alkoxy groups such as methoxy, ethoxy, and propoxy; halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; and substituted amino groups such as nitro group, cyano group, dimethylamino, dibenzylamino, and diphenylamino. . general formula general formula R 5 and R 6 in the general formulas (4) and (5) represent a group selected from an alkyl group, an aralkyl group, and an aryl group that may have a substituent. As a specific example of R 5 and R 6 above, the general formula
The same examples as R 3 and R 4 in (3) can be given. general formula general formula Y in the general formulas (6) and (7) represents a divalent aromatic hydrocarbon group or a divalent heterocyclic group containing a nitrogen atom in the ring. The divalent group of the aromatic hydrocarbon mentioned above is 0-
Divalent groups of monocyclic aromatic hydrocarbons such as phenylene, 0-naphthylene, perinaphthylene, 1,2-
Examples of divalent groups of polycyclic aromatic hydrocarbons such as anthrylene and 9,10-phenanthrylene include heterocyclic divalent groups containing a nitrogen atom in the ring.
For example, 3,4-pyrazolediyl, 2,3-pyridinediyl, 4,5-pyrimidinediyl, 6,7
-imidazolediyl, 5,6-benzimidazolediyl, 6,7-quinolinediyl, and other 5- or 6-membered heterocyclic groups that are divalent. general formula In the formula, R 7 and R 8 are a hydrogen atom, a group selected from an alkyl group, an aralkyl group, an aryl group, and a heterocyclic group which may have a substituent, or 5 together with the carbon atom to which R 7 and R 8 are bonded. This 5- or 6-membered ring may have a fused aromatic ring, and Z is a naphthalene ring, an anthracene ring, a carbazole ring fused with a benzene ring, Indicates a residue necessary to form a polycyclic aromatic ring or a heterocycle selected from a benzcarbazole ring, a dibenzofuran ring, a benzonaphthofuran ring, and a diphenylene sulfide ring. Specific examples of the alkyl group mentioned above include methyl, ethyl, propyl, butyl, etc. Specific examples of the aralkyl group include benzyl, phenethyl, naphthylmethyl, etc. Specific examples of the aryl group include phenyl, naphthyl, anthryl, and pyrenyl. Specific examples of heterocyclic groups include pyridyl,
Examples include groups such as thienyl, furyl, and carbazoyl, and further examples of substituents that the above groups may have include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom, methyl, ethyl, propyl, Alkyl groups such as butyl, alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, substituted amino groups such as nitro group, cyano group, dimethylamino, diethylamino, dipropylamino, dibenzylamino, diphenylamino, morpholino, piperidino, pyrrolidino, etc. can be mentioned. the above
5-membered or 6-membered with bonded carbon atoms of R 7 and R 8
Specific examples of groups which are residues forming a membered ring, and this 5- or 6-membered ring may have a condensed aromatic ring include groups such as cyclopentylidene, cyclohexylidene, and 9-xanthenylidene. Can be mentioned. general formula In the formula, R 9 and R 10 are a hydrogen atom, a group selected from an alkyl group, an aralkyl group, an aryl group, and a heterocyclic group which may have a substituent, or 5 together with the carbon atom to which R 9 and R 10 are bonded. This 5- or 6-membered ring may have a fused aromatic ring, and Z is a naphthalene ring, an anthracene ring, a carbazole ring fused with a benzene ring, Indicates a residue necessary to form a polycyclic aromatic ring or a heterocycle selected from a benzcarbazole ring, a dibenzofuran ring, a benzonaphthofuran ring, and a diphenylene sulfide ring. Specific examples of the alkyl group in the above group include methyl,
Examples of groups such as ethyl, propyl, and butyl; specific examples of aralkyl groups include groups such as benzyl, phenethyl, and naphthylmethyl; specific examples of aryl groups include groups such as phenyl, diphenyl, naphthyl, anthryl, and pyrenyl; and heterocyclic groups. Specific examples include groups such as pyridyl, thienyl, furyl, and carbazoyl, and further substituents that the above groups may have include halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom, methyl , alkyl groups such as ethyl, propyl, butyl, alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, nitro group, cyano group, dimethylamino, diethylamino, dipropylamino, dibenzylamino, diphenylamino, morpholino, piperidino, pyrrolidino, etc. Examples include substituted amino groups. Specific examples of residues that form a 5- or 6-membered ring together with the bonded carbon atoms of R 9 and R 10 above, and this 5- or 6-membered ring may have a fused aromatic ring include: Examples include groups such as cyclopentylidene, cyclohexylidene, and 9-xanthenylidene. Specific examples of the disazo pigment represented by the general formula (1) are shown below. In addition to these exemplary pigments, there are many disazo pigments included in general formula (1). The polycarbonate Z resin represented by the general formula (2) has (a) good transparency, (b) high electrical insulation and withstand voltage, and (c) a hard surface with appropriate lubricity. (d) It has excellent stability when dissolved in a solvent. Ordinary polycarbonate resin, i.e. Bisphenol A type polycarbonate resin, which has the structural formula different. By combining the specific disazo pigment of the present invention with polycarbonate Z resin, the extent to which a barrier layer is formed at the interface between the pigment particles and the resin to prevent charge movement during light irradiation is much greater than when combining with other than polycarbonate Z resin. The benzene ring and cyclohexyl group of the polycarbonate Z resin structure facilitate charge transfer and seem to improve sensitivity. The form of the electrophotographic photoreceptor according to the present invention includes (a) a photosensitive layer in which a disazo pigment represented by general formula (1) (hereinafter referred to as "disazo pigment") is dispersed in polycarbonate Z resin; (b) disazo pigment (c) Disazo pigment dispersed in a binder resin (polycarbonate Z resin or other resin may be used) ) is used as a charge generation layer, and a functionally separated photosensitive layer is formed by laminating a charge transport layer containing a polycarbonate Z resin and a charge transport substance thereon; (d) a disazo pigment and a polycarbonate Z resin are placed on the charge transport layer; Examples include a functionally separated photosensitive layer in which a charge generation layer containing the following is laminated. Examples of electron-donating compounds include polycyclic aromatic rings such as anthracene, pyrene, phenanthrene, and coronene in the main chain or side chain, or indole, carbazole,
Oxazole, isoxazole, thiazole,
imidazole, pyrazole, oxadiazole,
Examples include compounds having nitrogen-containing heterocycles such as pyrazoline, thiadiazole, and triazole, hydrazone compounds, and aromatic amino compounds. Examples of electron-accepting compounds include aliphatic cyclic compounds, aromatic compounds, and heterocyclic compounds having electron-accepting substituents such as nitro, nitroso, and cyano groups, such as tetracyanoethylene, trinitrobenzene, Dinitroacetophenone, trinitroanisole, tetranitronaphthalene, terephthalonitrile, isophthalonitrile, benzoyl cyanide, quinoline cyanide, cyanopyridine, nitroanthracene, dinitrofluorenone, trinitrofluorenone, tetranitrofluorenone, tetracyanopyrene etc. Electron-accepting compounds are generally not preferred due to their carcinogenicity and other harmful properties. When an electron donating compound is used, the above-mentioned form (c) is used for negative charging, and the form (d) is used for positive charging. The charge transport layer contains a charge transport material and a resin in a ratio of 5:1 to 5:1.
It is formed by mixing at a ratio of about 1:2 (weight ratio), and the film thickness is about 5 to 20 μm. In addition to polycarbonate Z, polyester,
polyvinyl benzal, polyvinyl butyral,
Polyvinylpyrrolidone, methylcellulose, polyacrylic acid esters, cellulose esters, etc. are used as appropriate. Dispersion can be carried out by a conventional method such as a ball mill, roll mill, sand mill, or colloid mill after the pigment is mixed into the resin solution. The thickness of the charge generation layer is 0.01~1μ, preferably 0.05
~0.5μ. When formed on top of the charge transport layer, it is thicker, on the order of 0.5 to 5 microns, and the pigment to resin ratio is on the order of 5:1 to 1:2. [Effects of the Invention] In the electrophotographic photoreceptor of the present invention, the photosensitive layer containing a specific disazo pigment and polycarbonate Z resin has high sensitivity and low residual potential, and also has low charging and
The bright area potential is stable without increasing after repeated exposure, and the surface is coated with polycarbonate Z.
Due to the presence of resin, the surface has a high surface roughness and has excellent lubricity, making it difficult to get scratches and improving mechanical durability. Furthermore, since the polycarbonate Z resin solution has good storage stability, it can improve productivity and contribute to quality stabilization. [Examples] Examples 1 to 6 An aluminum cylinder with a wall thickness of 0.5 mm and a size of 60φ×260 mm was prepared as a base. Next, copolymerized nylon (product name CM8000, Toray Industries, Inc.)
(manufactured by Dainippon Ink Chemical Co., Ltd.) and 4 parts of Type 8 nylon (trade name Lacucamide 5003, manufactured by Dainippon Ink Chemical Co., Ltd.) were dissolved in 50 parts of methanol and 50 parts of n-butanol, and the solution was dip coated onto the above substrate to a thickness of 0.6μ. A polyamide undercoat layer was formed. Next, 10 parts of a disazo pigment selected from the exemplary disazo pigments of the general formula (1) and 10 parts of polyvinyl butyral (trade name Eslec BM-2, manufactured by Sekisui Chemical Co., Ltd.) were mixed with 120 parts of cyclohexanone in a sand mill. It was dispersed for 10 hours. 30 parts of methyl ethyl ketone was added to the dispersion and coated on the undercoat layer to form a charge generation layer with a thickness of 0.15 μm. Next, polycarbonate Z resin (Mitsubishi Gas Chemical Co., Ltd.)
Prepare 10 parts of a product (manufactured by) with a weight average molecular weight of 120,000,
Along with 10 parts of a hydrazone compound of the following structural formula, It was dissolved in 80 parts of monochlorobenzene. This was applied onto the charge generation layer to form a charge transport layer with a thickness of 16μ. Exemplary disazo pigments of the above selection (1), (9), (14), (16),
Electrophotographic photoreceptors of Examples 1 to 6 were prepared corresponding to (22) and (30). The electrophotographic photoreceptor thus produced was -
5.6KV corona charging, image exposure, dry toner development,
Toner transfer to plain paper, urethane rubber blade (altitude 70°, pressure 5Kgw/cm 2 , angle to photoconductor)
The electrophotographic properties were evaluated by attaching it to an electrophotographic copying machine that has a cleaning process at 20°). When the potential was measured, the dark potential (V D ) was -700V.
Potential when exposed to light of 10 lux/second (V L )
The results are shown in Table 1. Comparative Examples 1 to 4 Electrophotographic photoreceptors were prepared in the same manner as in Example 1, except that the following organic pigments A to D were used in place of the disazo pigment of Example 1 (Comparative examples corresponding to A to D Examples 1 to 4). The measurement results of electrophotographic properties are shown in Table 1. Organic pigment A β-type copper phthalocyanine (Dainippon Ink Chemical Co., Ltd.)
(However, it is a pigment produced by sequential hot filtration with water, ethanol, and methyl ethyl ketone)
【表】
以上のように、比較例に比べて実施例の電子写
真感光体は感度が高く、しかも、かぶりのない鮮
明な画像が得られた。
実施例 7
実施例1のジスアゾ顔料に代え前記例示顔料(4)
を用いた他は実施例1と同様な方法で電子写真感
光体を作成した。
比較例 5〜8
実施例7における電荷輸送層の形成の際に用い
たポリカーボネートZ樹脂に代え下記の樹脂を用
い、他は実施例7と同様の方法で電子写真感光体
を作成した。
比較例 5
アクリル樹脂(商品名BR−80、三菱レーヨン
(株)製)
比較例 6
ポリスチレン(商品名スタイロン−470、旭化
成(株)製)
比較例 7
フエノキシ樹脂(商品名YP40、東都化成(株)製)
比較例 8
ポリエステル(商品名バイロン−300、東洋紡
績(株)製)
これ等の電子写真感光体を用いて、実施例1と
同様なプロセスを有する電子写真複写機(但し、
露光量は7.2ルツクス・秒)により評価を行つた。
評価は、初期のVD、VL及び1万枚耐久後のVD、
VLさらに1万枚目の画像を見ることにより比較
した。結果を第2表に示した。[Table] As described above, the electrophotographic photoreceptor of the example had higher sensitivity than the comparative example, and moreover, clear images without fogging were obtained. Example 7 The above exemplary pigment (4) was used instead of the disazo pigment of Example 1.
An electrophotographic photoreceptor was produced in the same manner as in Example 1 except that the following was used. Comparative Examples 5 to 8 Electrophotographic photoreceptors were prepared in the same manner as in Example 7 except that the following resins were used in place of the polycarbonate Z resin used in forming the charge transport layer in Example 7. Comparative example 5 Acrylic resin (product name BR-80, Mitsubishi Rayon
Comparative Example 6 Polystyrene (product name Styron-470, manufactured by Asahi Kasei Co., Ltd.) Comparative Example 7 Phenoxy resin (product name YP40, manufactured by Toto Kasei Co., Ltd.) Comparative Example 8 Polyester (product name Vylon-300, manufactured by Toto Kasei Co., Ltd.) (manufactured by Toyobo Co., Ltd.) An electrophotographic copying machine having the same process as in Example 1 using these electrophotographic photoreceptors (however,
The evaluation was performed using the exposure amount (7.2 lux·sec).
The evaluation is initial V D , V L and V D after 10,000 sheets durability,
V L A further comparison was made by looking at the 10,000th image. The results are shown in Table 2.
【表】
発生
[Table] Occurrence
【表】
るかぶり発
生
以上のように1万回の耐久性において、特にポ
リカーボネートZ樹脂を使用した本発明の実施例
は、感度、電位安定性及び画質の面で優れている
ことを証明した。
比較例 9
実施例7における電荷輸送層の形成の際に用い
たポリカーボネートZ樹脂に代えポリカーボネー
トA樹脂(商品名バンライトL−1250、帝人化成
(株)製)を用い、他は実施例7と同様の方法で電子
写真感光体を作成した場合、電子写真感光体とし
ての特性は、VLで実験誤差程度の0〜10Vの変
化であり、大差はなかつた。
しかし、ポリカーボネートA樹脂とヒドラゾン
化合物の樹脂溶液は、24時間後において粘度が3
〜4倍に上昇し、48時間後にはゲル化して流動性
が失われたのに対し、ポリカーボネートZ樹脂の
場合は48時間後においても年度変化が全くなく、
溶液安定性の面で著しく優れていた。
実施例 8
ポリビニルカルバゾール(重量平均分子量6万
のもの)10部とm−ターフエニル2部をモノクロ
ルベンゼン80部及び塩化メチレン20部に溶解し
た。
これを実施例1と同様に形成した下引層上に浸
漬塗布し、18μ厚の電荷輸送層を設けた。
次に前記例示顔料(6)のジスアゾ顔料10部をポリ
カーボネートZ樹脂(帝人化成(株)製、重量平均分
子量15万のもの)の8%シクロヘキサノン溶液
250部に加えサンドミル装置で10時間分散した。
この分散液を上記電荷輸送層上にドラムを回転さ
せながらスプレー塗布した。このようにして3μ
厚の電荷発生層を形成した。
この電子写真感光体を実施例1と同様の電子写
真複写機に取り付けて評価した。但し、コロナ帯
電は+5.2KVとした。
結果はVDが700V、7.5ルツクス・秒露光させた
場合のVLは140Vであり、良好な画像を得ること
ができ、実施例7と同等の結果を得ることができ
た。
一方、比較例5〜8と同様に樹脂を代えて電子
写真感光体を作成しても、やはり比較例5〜8と
同様の結果であつた。
実施例 9
実施例1のジスアゾ顔料に代えて前記例示顔料
(2)のジスアゾ顔料を用いた他は実施例と同様な方
法で電子写真感光体を作成した。
こうして作成した電子写真感光体に−5KVの
コロナ放電を行つた。この時の表面電位を測定し
た(初期電位Vp)。
さらに、この電子写真感光体を5秒間暗所で放
置した後の表面電位(暗減衰VK)を測定した。
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E1/2μJ/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/
ヒ素の三元素半導体レーザー(出力5mW、発振
波長778nm)を用いた。
この結果は次のとおりであつた。
Vp:−680V、VK:98%、
E1/2:0.9μJ/cm2
次に同上の半導体レーザーを備えた反転現像方
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(商品名LBP−CX、キヤノン(株)
製)に上記電子写真感光体を該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
を行なつた。条件は以下のとおりである。
一次帯電後の表面電位:−700V、
像露光後の表面電位:−150V
(露光2μJ/cm2)、
転写電位:+700V、現像剤極性:負極性、
プロセススピード: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:50ルツクス・秒の赤色全面露
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なつた。
1万枚コピーの結果かぶりのない鮮明な画像が
得られた。
一方、比較例5〜8と同様に樹脂を代えて作成
した電子写真感光体の画像は画像濃度が低かつた
り、かぶりが発生していたりしており良好な画像
が得られなかつた。[Table] From Kaburi
As described above, in terms of durability after 10,000 cycles, the examples of the present invention using polycarbonate Z resin in particular proved to be excellent in terms of sensitivity, potential stability, and image quality. Comparative Example 9 Polycarbonate A resin (trade name Vanlite L-1250, Teijin Kasei Co., Ltd.) was used instead of polycarbonate Z resin used in forming the charge transport layer in Example 7.
When an electrophotographic photoreceptor was produced using the same method as in Example 7, the characteristics as an electrophotographic photoreceptor were as follows. , there was no significant difference. However, the resin solution of polycarbonate A resin and hydrazone compound had a viscosity of 3 after 24 hours.
In contrast, polycarbonate Z resin showed no change at all even after 48 hours, and the fluidity was lost after 48 hours.
It was significantly superior in terms of solution stability. Example 8 10 parts of polyvinyl carbazole (weight average molecular weight 60,000) and 2 parts of m-terphenyl were dissolved in 80 parts of monochlorobenzene and 20 parts of methylene chloride. This was applied by dip coating onto the undercoat layer formed in the same manner as in Example 1 to provide a charge transport layer with a thickness of 18 μm. Next, 10 parts of the disazo pigment of the exemplary pigment (6) was added to an 8% cyclohexanone solution of polycarbonate Z resin (manufactured by Teijin Kasei Ltd., weight average molecular weight 150,000).
In addition to 250 parts, the mixture was dispersed in a sand mill for 10 hours.
This dispersion was spray coated onto the charge transport layer while rotating the drum. In this way 3μ
A thick charge generation layer was formed. This electrophotographic photoreceptor was attached to the same electrophotographic copying machine as in Example 1 and evaluated. However, the corona charge was set to +5.2KV. As a result, V D was 700 V, and V L was 140 V when exposed at 7.5 lux/second, and a good image could be obtained, and the same results as in Example 7 could be obtained. On the other hand, even when electrophotographic photoreceptors were produced using different resins in the same manner as in Comparative Examples 5 to 8, the results were still similar to those in Comparative Examples 5 to 8. Example 9 The above exemplified pigment was used in place of the disazo pigment of Example 1.
An electrophotographic photoreceptor was prepared in the same manner as in Example except that the disazo pigment (2) was used. A corona discharge of -5 KV was applied to the electrophotographic photoreceptor thus prepared. The surface potential at this time was measured (initial potential V p ). Furthermore, the surface potential (dark decay V K ) of this electrophotographic photoreceptor was measured after it was left in a dark place for 5 seconds. Sensitivity was evaluated by measuring the exposure amount E1/2 μJ/cm 2 required to attenuate the potential V K to 1/2 after dark decay. At this time, gallium/aluminum/
An arsenic three-element semiconductor laser (output 5 mW, oscillation wavelength 778 nm) was used. The results were as follows. Vp : -680V, VK : 98%, E1/2: 0.9μJ/cm Second , a laser beam printer (product name: LBP-CX), which is an electrophotographic printer using a reversal development method, is equipped with the same semiconductor laser as above. , Canon Inc.
The above electrophotographic photoreceptor was replaced with the LBP-CX photoreceptor and set in an actual image forming test. The conditions are as follows. Surface potential after primary charging: -700V, surface potential after image exposure: -150V (exposure 2μJ/ cm2 ), 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 red full-surface exposure Image formation was performed by line scanning a laser beam in accordance with character and image signals. As a result of copying 10,000 copies, clear images with no fogging were obtained. On the other hand, images of electrophotographic photoreceptors prepared using different resins in the same manner as in Comparative Examples 5 to 8 had low image density and fog, and good images could not be obtained.
Claims (1)
くとも1種と下記一般式(2)で示されるポリカーボ
ネートZ樹脂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 式中、Aはフエノール性OH基を有するカツプ
ラー残基を示し、R1、R1′、R2及びR2′は水素原
子、ハロゲン原子又は置換基を有してもよいアル
キル基、アルコキシ基及びアラルキル基から選ば
れる基を示す。 一般式 式中、nは平均重合度を示し、50〜5000の範囲
である。 2 一般式(1)中のAが、下記一般式(3)乃至(9)で示
されるフエノール性OH基を有するカツプラー残
基から選ばれ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なるナフタレ
ン環、アントラセン環、カルバゾール環、ベンズ
カルバゾール環、ジベンゾフラン環、ベンゾナフ
トフラン環及びジフエニレンサルフアイド環から
選ばれる多環芳香環又はヘテロ環を形成するに必
要な残基を示し、R3及びR4は水素原子、置換基
を有してもよいアルキル基、アラルキル基、アリ
ール基及びヘテロ環基から選ばれる基、又はR3、
R4の結合する窒素原子とともに形成する環状ア
ミノ基を示す。 一般式 一般式 一般式(4)、(5)中のR5及びR6は置換基を有して
もよいアルキル基、アラルキル基及びアリール基
から選ばれる基を示す。 一般式 一般式 一般式(6)及び(7)中のYは芳香族炭化水素の2価
の基又は窒素原子を環内に含むヘテロ環の2価の
基を示す。 一般式 式中、R7及びR8は水素原子、置換基を有して
もよいアルキル基、アラルキル基、アリール基及
びヘテロ環基から選ばれる基、又はR7、R8の結
合する炭素原子とともに5員あるいは6員環を形
成する残基を示し、この5員あるいは6員環は縮
合芳香族環を有してもよく、Zはベンゼン環と縮
合してなるナフタレン環、アントラセン環、カル
バゾール環、ベンズカルバゾール環、ジベンゾフ
ラン環、ベンゾナフトフラン環及びジフエニレン
サルフアイド環から選ばれる多環芳香環、又はヘ
テロ環を形成するに必要な残基を示す。 一般式 式中、R9及びR10は水素原子、置換基を有して
もよいアルキル基、アラルキル基、アリール基及
びヘテロ環基から選ばれる基、又はR9、R10の結
合する炭素原子とともに5員あるいは6員環を形
成する残基を示し、この5員あるいは6員環は縮
合芳香族環を有してもよく、Zはベンゼン環と縮
合してなるナフタレン環、アントラセン環、カル
バゾール環、ベンズカルバゾール環、ジベンゾフ
ラン環、ベンゾナフトフラン環及びジフエニレン
サルフアイド環から選ばれる多環芳香環、又はヘ
テロ環を形成するに必要な残基を示す。 3 感光層が一般式(1)のジスアゾ顔料を電荷発生
材とし、電荷輸送材と一般式(2)のポリカーボネー
トZ樹脂の中に分散したものである特許請求の範
囲第1項又は第2項記載の電子写真感光体。 4 感光層が一般式(1)のジスアゾ顔料を含む電荷
発生層と電荷輸送材と一般式(2)のポリカーボネー
トZ樹脂を含む電荷輸送層を積層したものである
特許請求の範囲第1項又は第2項記載の電子写真
感光体。 5 感光層が電荷輸送層の上に一般式(1)のジスア
ゾ顔料と一般式(2)のポリカーボネートZ樹脂を含
む電荷発生層を積層したものである特許請求の範
囲第1項又は第2項記載の電子写真感光体。[Scope of Claims] 1. An electrophotographic photosensitive layer comprising a photosensitive layer containing at least one disazo pigment represented by the following general formula (1) and a polycarbonate Z resin represented by the following general formula (2). body. general formula In the formula, A represents a coupler residue having a phenolic OH group, and R 1 , R 1 ′, R 2 and R 2 ′ are a hydrogen atom, a halogen atom, or an alkyl group or alkoxy group which may have a substituent. and an aralkyl group. general formula In the formula, n represents the average degree of polymerization and is in the range of 50 to 5000. 2. The electrophotographic photoreceptor according to claim 1, wherein A in the general formula (1) is selected from coupler residues having a phenolic OH group represented by the following general formulas (3) to (9). general formula In the formula, Indicates the residue necessary to form a hydrogen atom, R 3 and R 4 are a group selected from a hydrogen atom, an alkyl group that may have a substituent, an aralkyl group, an aryl group, and a heterocyclic group, or R 3 ,
Indicates a cyclic amino group formed with the nitrogen atom to which R 4 is bonded. general formula general formula R 5 and R 6 in the general formulas (4) and (5) represent a group selected from an alkyl group, an aralkyl group, and an aryl group that may have a substituent. general formula general formula Y in the general formulas (6) and (7) represents a divalent aromatic hydrocarbon group or a divalent heterocyclic group containing a nitrogen atom in the ring. general formula In the formula, R 7 and R 8 are a hydrogen atom, a group selected from an alkyl group, an aralkyl group, an aryl group, and a heterocyclic group which may have a substituent, or 5 together with the carbon atom to which R 7 and R 8 are bonded. This 5- or 6-membered ring may have a fused aromatic ring, and Z is a naphthalene ring, an anthracene ring, a carbazole ring fused with a benzene ring, Indicates a residue necessary to form a polycyclic aromatic ring or a heterocycle selected from a benzcarbazole ring, a dibenzofuran ring, a benzonaphthofuran ring, and a diphenylene sulfide ring. general formula In the formula, R 9 and R 10 are a hydrogen atom, a group selected from an alkyl group, an aralkyl group, an aryl group, and a heterocyclic group which may have a substituent, or 5 together with the carbon atom to which R 9 and R 10 are bonded. This 5- or 6-membered ring may have a fused aromatic ring, and Z is a naphthalene ring, an anthracene ring, a carbazole ring fused with a benzene ring, Indicates a residue necessary to form a polycyclic aromatic ring or a heterocycle selected from a benzcarbazole ring, a dibenzofuran ring, a benzonaphthofuran ring, and a diphenylene sulfide ring. 3. Claims 1 or 2, wherein the photosensitive layer comprises a disazo pigment of general formula (1) as a charge generating material, dispersed in a charge transporting material and a polycarbonate Z resin of general formula (2). The electrophotographic photoreceptor described above. 4. Claim 1, wherein the photosensitive layer is a laminate of a charge generation layer containing a disazo pigment of general formula (1), a charge transport material, and a charge transport layer containing a polycarbonate Z resin of general formula (2), or The electrophotographic photoreceptor according to item 2. 5. Claims 1 or 2, wherein the photosensitive layer is a charge-generating layer containing a disazo pigment of general formula (1) and a polycarbonate Z resin of general formula (2) laminated on a charge transport layer. The electrophotographic photoreceptor described above.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21805485A JPS6278559A (en) | 1985-10-02 | 1985-10-02 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21805485A JPS6278559A (en) | 1985-10-02 | 1985-10-02 | Electrophotographic sensitive body |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6278559A JPS6278559A (en) | 1987-04-10 |
JPH0547102B2 true JPH0547102B2 (en) | 1993-07-15 |
Family
ID=16713928
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP21805485A Granted JPS6278559A (en) | 1985-10-02 | 1985-10-02 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6278559A (en) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57146257A (en) * | 1981-03-04 | 1982-09-09 | Ricoh Co Ltd | Composite electrophotographic receptor |
JPS58132242A (en) * | 1982-01-30 | 1983-08-06 | Mita Ind Co Ltd | Electrophotographic receptor |
JPS5971057A (en) * | 1982-10-18 | 1984-04-21 | Nippon Telegr & Teleph Corp <Ntt> | Electrophotogaphic receptor |
JPS60172044A (en) * | 1984-02-16 | 1985-09-05 | Konishiroku Photo Ind Co Ltd | Preparation of photosensitive body |
-
1985
- 1985-10-02 JP JP21805485A patent/JPS6278559A/en active Granted
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57146257A (en) * | 1981-03-04 | 1982-09-09 | Ricoh Co Ltd | Composite electrophotographic receptor |
JPS58132242A (en) * | 1982-01-30 | 1983-08-06 | Mita Ind Co Ltd | Electrophotographic receptor |
JPS5971057A (en) * | 1982-10-18 | 1984-04-21 | Nippon Telegr & Teleph Corp <Ntt> | Electrophotogaphic receptor |
JPS60172044A (en) * | 1984-02-16 | 1985-09-05 | Konishiroku Photo Ind Co Ltd | Preparation of photosensitive body |
Also Published As
Publication number | Publication date |
---|---|
JPS6278559A (en) | 1987-04-10 |
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