JPH052983B2 - - Google Patents
Info
- Publication number
- JPH052983B2 JPH052983B2 JP62299045A JP29904587A JPH052983B2 JP H052983 B2 JPH052983 B2 JP H052983B2 JP 62299045 A JP62299045 A JP 62299045A JP 29904587 A JP29904587 A JP 29904587A JP H052983 B2 JPH052983 B2 JP H052983B2
- Authority
- JP
- Japan
- Prior art keywords
- thioether
- group
- layer
- electrophotographic photoreceptor
- charge
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 28
- 150000003568 thioethers Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 51
- 150000001875 compounds Chemical class 0.000 description 18
- 239000000975 dye Substances 0.000 description 17
- 239000000049 pigment Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000011230 binding agent Substances 0.000 description 10
- -1 hydrazone compounds Chemical class 0.000 description 10
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002800 charge carrier Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920002382 photo conductive polymer Polymers 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 230000005496 eutectics Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- 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 2
- 235000021240 caseins Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 2
- 229920001778 nylon 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
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 2
- 239000012989 trithiocarbonate Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- HIPJINRMIDCBDO-UHFFFAOYSA-N 2,6,6-trimethylcyclohexa-1,3-diene Chemical compound CC1=CC(C)(C)CC=C1 HIPJINRMIDCBDO-UHFFFAOYSA-N 0.000 description 1
- ZAKUXPKAPWYKQK-UHFFFAOYSA-N 3h-oxathiadiazole Chemical compound N1SOC=N1 ZAKUXPKAPWYKQK-UHFFFAOYSA-N 0.000 description 1
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-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
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- ZTWQZJLUUZHJGS-UHFFFAOYSA-N Vat Yellow 4 Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C4=CC=CC=C4C(=O)C4=C3C2=C1C=C4 ZTWQZJLUUZHJGS-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- JWGLGQHIGMBQRK-UHFFFAOYSA-N [3-(4-chlorophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-phenylmethanone Chemical class C1=CC(Cl)=CC=C1C1N(C(=O)C=2C=CC=CC=2)N=C(C=2SC=CC=2)C1 JWGLGQHIGMBQRK-UHFFFAOYSA-N 0.000 description 1
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical group [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000011648 beta-carotene Substances 0.000 description 1
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 1
- 235000013734 beta-carotene Nutrition 0.000 description 1
- 229960002747 betacarotene Drugs 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- UUWRXRHMQFTLIQ-UHFFFAOYSA-M bis(2-chloroethyl)-[4-(2,6-diphenylthiopyran-4-ylidene)cyclohexa-2,5-dien-1-ylidene]azanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC(=[N+](CCCl)CCCl)C=CC1=C1C=C(C=2C=CC=CC=2)SC(C=2C=CC=CC=2)=C1 UUWRXRHMQFTLIQ-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical compound [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 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
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000007760 metering rod coating Methods 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- 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
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/062—Acyclic or carbocyclic compounds containing non-metal elements other than hydrogen, halogen, oxygen or nitrogen
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
- G03G5/0629—Heterocyclic compounds containing one hetero ring being five-membered containing one hetero atom
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
- G03G5/0631—Heterocyclic compounds containing one hetero ring being five-membered containing two hetero atoms
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
- G03G5/0633—Heterocyclic compounds containing one hetero ring being five-membered containing three hetero atoms
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
- G03G5/0637—Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
- G03G5/0638—Heterocyclic compounds containing one hetero ring being six-membered containing two hetero atoms
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
- G03G5/064—Heterocyclic compounds containing one hetero ring being six-membered containing three hetero atoms
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0642—Heterocyclic compounds containing one hetero ring being more than six-membered
-
- 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0644—Heterocyclic compounds containing two or more hetero rings
- G03G5/0646—Heterocyclic compounds containing two or more hetero rings in the same ring system
-
- 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
- G03G5/0698—Compounds of unspecified structure characterised by a substituent only
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
〔産業上の利用分野〕
本発明は、電子写真感光体に関し、詳しくは改
善された電子写真特性を与える低分子の有機光導
電体を有する電子写真感光体に関するものであ
る。
〔従来技術〕
従来、電子写真感光体で用いる光導電材料とし
て、ポリビニルカルバゾールをはじめとする各種
の有機光導電性ポリマーが提案されて来たが、こ
れらのポリマーは、無機系光導電材料に較べ成膜
性、軽量性などの点で優れているにもかかわらず
今日までその実用化が困難であつたのは、未だ十
分な成膜性が得られておらず、また感度、耐久性
および環境変化による安定性の点で無機系光導電
材料に較べ劣つているためであつた。また、米国
特許第4150987号公報などに開示のヒドラゾン化
合物、米国特許第3837851号公報などに記載のト
リアリールピラゾリン化合物、特開昭51−94828
号公報、特開昭51−94829号公報などに記載の9
−スチリルアントラセン化合物などの低分子の有
機光導電体が提案されている。この様な低分子の
有機光導電体は、使用するバインダーを適当に選
択することによつて、有機光導電性ポリマーの分
野で問題となつていた成膜性の欠点を解消できる
様になつたが、感度の点で十分なものとは言えな
い。
このようなことから、近年感光層を電荷発生層
と電荷輸送層に機能分離させた積層構造体が提案
された。この積層構造を感光層とした電子写真感
光体は、可視光に対する感度、電荷保持力、表面
強度などの点で改善できるようになつた。この様
な電子写真感光体は、例えば米国特許第3837851
号、同第3871882号公報などに開示されている。
しかし、従来の低分子の有機光導電体を電荷輸
送層に用いた電子写真感光体では、感度、特性
が、実用レベルに達していても、繰り返し帯電お
よび露光を行なつた際には明部電位と暗部電位の
変動が大きいという欠陥は十分に解決されていな
い。この繰り返し使用時における電位の変動を抑
えるため、例えば特開昭57−122444号、特開昭62
−39863号には電荷輸送層中に酸化防止剤を混在
せしめる方法が開示されており、他にも特開昭53
−26128号、特開昭60−164745号、特開昭62−
105151号等に添加剤を加えて安定化させる方法が
記載されている。しかし、これらの方法では特に
繰り返し使用が長期にわたる時は効果が十分でな
いのが現状である。
〔発明が解決しようとする問題点〕
本発明の目的は、前述の欠点又は不利を解消し
た電子写真感光体を提供することにある。
本発明の別の目的は新規な有機光導電体を提供
することにある。
本発明の他の目的は電荷輸送層と電荷輸送層に
機能分離した積層感光層における新規な電荷輸送
物質を提供することにある。
〔問題点を解決するための手段〕
本発明は、導電性支持体上に感光層を有する電
子写真感光体において、該感光層が一般式()
で示されるチオエーテル化合物を含有することを
特徴とする電子写真感光体である。
一般式
式中R1およびR2はメチル,エチル,プロピル,
ブチル等のアルキル基、ベンジル,フエネチル,
ナフチルメチル等のアラルキル基またはフエニ
ル,ナフチル,アンスリル,ビフエニル等のアリ
ール基を表わす。またR1およびR2は結合して5
ないし6員環を形成するのに必要な残基を示す。
また、前記のアルキル基,アラルキル基、および
アリール基は置換基を有しても構わない。これら
の置換基としては、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、ベンジ
ル,フエネチル,ナフチルメチル等のアキル基、
フツ素,塩素,臭素,沃素等のハロゲン原子、メ
チルチオ,エチルチオ,ブチルチオ等のアルキル
チオ基,ベンジレチオ,フエネチルチオ等のアラ
ルキルチオ基又はフエニルチオ,ナフチルチオ,
ビフエニルチオ等のアリールチオ基等が挙げられ
る。
Arは置換基を有してもよいフエニレン,ナフ
チレン,アンスリレン,ビフエニレン,フエナン
トリレン等のアリーレン基又はピリジン,キノリ
ン,インドール,カルバソール,チオフエン,ベ
ンゾチオフエン,アクリジン,フエノチアジン,
フエノキサジン,フエナジン,ベンゾフランン,
ジベンゾフラン,ベンゾオキサゾール,ベンゾチ
アゾール,ベンゾトリアゾール,オキジアゾー
ル,オキサチアジアゾール等から誘導される2価
のヘテロ環基を示す。これらの置換基としては
R1およびR2に用いられるものと同様な基が挙げ
られる。また、nは0又は1の整数を表わす。X
はS−R3または
[Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a low molecular weight organic photoconductor that provides improved electrophotographic properties. [Prior Art] Various organic photoconductive polymers, including polyvinylcarbazole, have been proposed as photoconductive materials for use in electrophotographic photoreceptors, but these polymers have poor performance compared to inorganic photoconductive materials. Although it has excellent film formability and light weight, it has been difficult to put it into practical use until now because sufficient film formability has not yet been obtained, and sensitivity, durability, and environmental This is because they are inferior to inorganic photoconductive materials in terms of stability due to changes. In addition, hydrazone compounds disclosed in U.S. Patent No. 4150987, triarylpyrazoline compounds disclosed in U.S. Patent No. 3837851, and JP-A-51-94828
No. 9 described in Japanese Patent Application Laid-open No. 51-94829, etc.
- Low molecular weight organic photoconductors such as styryl anthracene compounds have been proposed. By appropriately selecting the binder used, such low-molecular-weight organic photoconductors can overcome the film-forming problems that had been a problem in the field of organic photoconductive polymers. However, it cannot be said to be sufficient in terms of sensitivity. For these reasons, a laminated structure in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer has been proposed in recent years. Electrophotographic photoreceptors using this laminated structure as a photosensitive layer can now be improved in terms of sensitivity to visible light, charge retention, surface strength, and the like. Such an electrophotographic photoreceptor is disclosed in, for example, US Pat. No. 3,837,851.
No. 3871882, etc. However, in electrophotographic photoreceptors that use conventional low-molecular organic photoconductors in the charge transport layer, even if the sensitivity and characteristics have reached a practical level, bright areas deteriorate when repeatedly charged and exposed. The drawback of large fluctuations in potential and dark potential has not been fully resolved. In order to suppress the potential fluctuation during repeated use, for example, JP-A-57-122444, JP-A-62
-39863 discloses a method of mixing an antioxidant in a charge transport layer, and there is also a method published in JP-A-53
−26128, JP-A-60-164745, JP-A-62-
No. 105151 etc. describes a method of stabilizing by adding additives. However, the current situation is that these methods are not sufficiently effective, especially when repeatedly used over a long period of time. [Problems to be Solved by the Invention] An object of the present invention is to provide an electrophotographic photoreceptor that eliminates the above-mentioned drawbacks or disadvantages. Another object of the invention is to provide a new organic photoconductor. Another object of the present invention is to provide a novel charge transport material in a laminated photosensitive layer in which a charge transport layer and a charge transport layer are functionally separated. [Means for Solving the Problems] The present invention provides an electrophotographic photoreceptor having a photosensitive layer on a conductive support, wherein the photosensitive layer has the general formula ()
This is an electrophotographic photoreceptor characterized by containing a thioether compound represented by: general formula In the formula, R 1 and R 2 are methyl, ethyl, propyl,
Alkyl groups such as butyl, benzyl, phenethyl,
It represents an aralkyl group such as naphthylmethyl or an aryl group such as phenyl, naphthyl, anthryl, biphenyl. Also, R 1 and R 2 are combined to 5
Residues necessary to form a 6-membered ring are shown.
Further, the alkyl group, aralkyl group, and aryl group described above may have a substituent. These substituents include methyl, ethyl, propyl,
Alkyl groups such as butyl, alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, alkyl groups such as benzyl, phenethyl, naphthylmethyl,
Halogen atoms such as fluorine, chlorine, bromine, and iodine, alkylthio groups such as methylthio, ethylthio, and butylthio, aralkylthio groups such as benzylethio, phenethylthio, or phenylthio, naphthylthio,
Examples include arylthio groups such as biphenylthio. Ar is an arylene group such as phenylene, naphthylene, anthrylene, biphenylene, and phenanthrylene, which may have a substituent, or pyridine, quinoline, indole, carbazole, thiophene, benzothiophene, acridine, phenothiazine,
Phenoxazine, phenazine, benzofuran,
Indicates a divalent heterocyclic group derived from dibenzofuran, benzoxazole, benzothiazole, benzotriazole, oxadiazole, oxathiadiazole, etc. These substituents include
Groups similar to those used for R 1 and R 2 can be mentioned. Further, n represents an integer of 0 or 1. X
is S-R 3 or
【式】を示し、YはS−R3、
置換基を有してもよいアルキル基,アラルキル基
またはアリール基を示し、XおよびYのいずれ
か、あるいは両方にチオエーテル構造を有してい
る。R3およびR4は前述したR1およびR2と同義で
ある。また置換基を有してもよいアルキル基,ア
ラルキル基およびアリール基の具体例は前述した
R1およびR2と同義である。さらに、XとYは結
合して[Formula], Y represents S-R 3 , an alkyl group, an aralkyl group, or an aryl group which may have a substituent, and either or both of X and Y has a thioether structure. R 3 and R 4 have the same meanings as R 1 and R 2 described above. Specific examples of alkyl groups, aralkyl groups, and aryl groups that may have substituents are listed above.
Synonymous with R 1 and R 2 . Furthermore, X and Y are combined
【式】【formula】
【式】
のようなチオエーテル環を形成するのに必要な残
基を示す(mは2,3または4の整数、Zは縮合
芳香環を示す)。
一般式[]に示される新規の化合物を感光層
に含有せしめた電子写真感光体は、高感度であ
り、かつ、特に長期的な繰り返し帯電、露光によ
る電位変動も著しく小さくなる。
この理由は定かではないが、オゾン,NOx,
硝酸等複写機の機内で発生する環境劣化因子に対
して、The residues necessary to form a thioether ring as shown in the formula are shown (m is an integer of 2, 3 or 4, and Z is a fused aromatic ring). An electrophotographic photoreceptor containing the novel compound represented by the general formula [] in its photosensitive layer has high sensitivity, and particularly, potential fluctuations caused by repeated charging and exposure over a long period of time are significantly reduced. The reason for this is not clear, but ozone, NOx,
Against environmental deterioration factors such as nitric acid that occur inside copying machines,
【式】のNの塩基性とチオエーテル構
造の硫黄原子のd軌道効果とが相乗的に働き、環
境劣化因子の内部浸透を防げているものと考えら
れる。ただしX,Yのうち一方が水素原子である
場合、その効果は小さい。
本発明の化合物は特に一般式[]において
Arがフエニレンで、且つXおよびYが共にS−
R3で示されるチオエーテル構造であるか、又は
結合してチオエーテル構造を2ケ所有するチオエ
ーテル環を形成するのに必要な残基であるような
チオエーテル構造が2つ以上の場合にその効果は
特に著しい。
以下に一般式〔〕で示される化合物について
その代表例を挙げる。
<化合物例>
次に前記化合物の合成例を示す。
(化合物No.17の合成法)
亜燐酸トリメチル23g(187mmol)と下記構
造のトリチオカルボネートIt is thought that the basicity of N in [Formula] and the d-orbital effect of the sulfur atom in the thioether structure work synergistically to prevent internal penetration of environmental deterioration factors. However, when one of X and Y is a hydrogen atom, the effect is small. The compounds of the invention are particularly represented by the general formula []
Ar is phenylene, and both X and Y are S-
This effect is particularly effective when there are two or more thioether structures, such as the thioether structure represented by R 3 , or the residues necessary to combine to form a thioether ring having two thioether structures. Significant. Representative examples of compounds represented by the general formula [] are listed below. <Compound example> Next, a synthesis example of the above compound will be shown. (Synthesis method of compound No. 17) Trimethyl phosphite 23g (187mmol) and trithiocarbonate with the following structure
【式】トリチオカルボネート
3.4g(22mmol)を窒素気流下、55℃に加熱3
時間攪拌、反応する。次に塩化メチレン35gに溶
解したP−ジフエニルアミノベンズアルデヒド
5.4g(20mmol)を加え55℃にて15時間反応を続
ける。次に反応液を一度減圧乾固してから塩化メ
チレン−石油エーテルの場合溶媒で再結を2回行
い、目的物5.3gを帯電白色結晶として得た。収
率71%、融点132〜133℃
元素分析値
理論値 測定値
C 73.56 73.59
H 5.64 5.60
N 3.73 3.76
尚、合成例以外の化合物についても、一般に類
似の方法か又は該当するアルデヒドと
[Formula] Trithiocarbonate 3.4g (22mmol) is heated to 55℃ under a nitrogen stream 3
Stir for an hour to react. Next, P-diphenylaminobenzaldehyde dissolved in 35 g of methylene chloride
Add 5.4 g (20 mmol) and continue the reaction at 55°C for 15 hours. Next, the reaction solution was once dried to dryness under reduced pressure, and in the case of methylene chloride-petroleum ether, recrystallization was performed twice with a solvent to obtain 5.3 g of the target product as charged white crystals. Yield 71%, melting point 132-133℃ Elemental analysis value Theoretical value Measured value C 73.56 73.59 H 5.64 5.60 N 3.73 3.76 Compounds other than the synthesis examples are generally prepared using similar methods or with the corresponding aldehyde.
【式】の如き活性メチレン基を有するジ
チオエーテルとを脱水縮合させる等の手法により
合成される。
本発明の好ましい具体例では、感光層を電荷発
生層と電荷輸送層に機能分離した電子写真感光体
の電荷輸送物質に前記一般式で示される化合物を
用いることができる。
本発明による電荷輸送層は、前記の一般式で示
される化合物と結着剤とを適当な溶剤に溶解せし
めた溶液を塗布し、乾燥せしめることにより形成
させることが好ましい。ここに用いる結着剤とし
ては、例えばポリアクリレート樹脂、ポリスルホ
ン樹脂、ポリアミド樹脂、アクリル樹脂、アクリ
ロニトリル樹脂、メタクリル樹脂、塩化ビニル樹
脂、酢酸ビニル樹脂、フエノール樹脂、エポキシ
樹脂、ポリエステル樹脂、アルキド樹脂、ポリカ
ーボネート、ポリウレタンあるいは共重合体樹脂
例えばスチレン−ブタジエンコポリマー、スチレ
ン−アクリロニトリルコポリマー、スチレン−マ
レイン酸コポリマーなどを挙げることができる。
また、このような絶縁性ポリマーの他に、ポリビ
ニルカルバゾール、ポリビニルアントラセンやポ
リビニルピレンなどの有機光導電性ポリマーも使
用できる。
この結着剤と本発明の電荷輸送物質との配合割
合は、結着剤100重量部当り電荷輸送物質を10〜
500重量とすることが好ましい。
電荷輸送層は、下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とるとともに、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。しかし、電荷輸送層は、電
荷発生層の上に積層されていることが望ましい。
この電荷輸送層は、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、5μm〜40μmであるが、
好ましい範囲は10μm〜30μmである。
この様な電荷輸送層を形成する際に用いる有機
溶剤は、使用する結着剤の種類によつて異なり、
又は電荷発生層や下述の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、シクロヘキサノンなどのケトン類、
N,N−ジメチルホルムアミド、N,N−ジメチ
ルアセトアミドなどのアミド類、ジメチルスルホ
キシドなどのスルホキシド類、テトラヒドロフラ
ン、ジオキサン、エチレングリコールモノメチル
エーテルなどのエーテル類、酢酸メチル、酢酸エ
チルなどのエステル類、クロロホルム、塩化メチ
レン、ジクロルエチレン、四塩化炭素、トリクロ
ルエチレンなどの脂肪族ハロゲン化炭化水素類あ
るいはベンゼン、トルエン、キシレン、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、マイヤーバーコーテイング法、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、一般的には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
とが好ましい。
本発明の電荷輸送層には、種々の添加剤を含有
させて用いることもできる。例えば、ジフエニ
ル、m−ターフエニル、ジブチルフタレートなど
の可塑剤、シリコンオイル、グラフト型シリコン
ポリマー、各種フルオロカーボン類などの表面潤
滑剤、ジシアノビニル化合物、カルバゾール誘導
体などの電位安定剤,β−カロチン,Ni錯体,
1,4−ジアザビシクロ〔2,2,2〕オクタン
などの酸化防止剤などを挙げることができる。
本発明で用いる電荷発生層は、セレン、セレン
−テルル、アモルフアスシリコン等の無機の電荷
発生物質、ピリリウム系染料、チアピリリウム系
染料、アズレニウム系染料、チアシアニン系染
料、キノシアニン系染料、アズレニウム系染料等
のカチオン染料、スクバリリウム塩系染料、フタ
ロシアニン系顔料、アントアントロン系顔料、ジ
ベンズピレンキノン系顔料、ピラントロン系顔料
等の多環キノン顔料、インジゴ系顔料、キナクリ
ドン系顔料、アゾ顔料等の有機の電荷発生物質か
ら選ばれた材料を単独ないしは組み合わせて用い
蒸着層あるいは塗布層として用いることができ
る。
本発明に使用される上記電荷発生物質のうち、
特にアゾ顔料は多岐にわたつているが、特に効果
の高いアゾ顔料の代表的構造例を以下に示す。
アゾ顔料の一般式として、下記のように中心骨
格をA,
A(−N=N−Cp)n
カプラー部分をCpとして表わせば(ここでn
=2,or3)、まずAの具体例としては次のような
ものが挙げられる。It is synthesized by a method such as dehydration condensation with a dithioether having an active methylene group as shown in the formula. In a preferred embodiment of the present invention, a compound represented by the above general formula can be used as a charge transport material in an electrophotographic photoreceptor in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer. The charge transport layer according to the present invention is preferably formed by applying a solution prepared by dissolving the compound represented by the above general formula and a binder in an appropriate solvent and drying the solution. Examples of the binder used here include polyacrylate resin, polysulfone resin, polyamide resin, acrylic resin, acrylonitrile resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, phenol resin, epoxy resin, polyester resin, alkyd resin, and polycarbonate. , polyurethane or copolymer resins such as styrene-butadiene copolymer, styrene-acrylonitrile copolymer, styrene-maleic acid copolymer, and the like.
In addition to such insulating polymers, organic photoconductive polymers such as polyvinylcarbazole, polyvinylanthracene, and polyvinylpyrene can also be used. The blending ratio of this binder and the charge transport substance of the present invention is 10 to 10 parts by weight of the charge transport substance per 100 parts by weight of the binder.
It is preferable to set it as 500 weight. The charge transport layer is electrically connected to the charge generation layer described below, 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. are doing. At this time, this charge transport layer may be laminated on or under the charge generation layer. However, it is desirable that the charge transport layer is laminated on the charge generation layer.
Since this charge transport layer has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary. Generally, it is 5 μm to 40 μm, but
The preferred range is 10 μm to 30 μm. The organic solvent used when forming such a charge transport layer varies depending on the type of binder used.
Alternatively, it is preferable to select a material that does not dissolve the charge generation layer or the subbing layer described below. Specific organic solvents include alcohols such as methanol, ethanol, and isopropanol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone;
Amides such as N,N-dimethylformamide and N,N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide, ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate, chloroform, Aliphatic halogenated hydrocarbons such as methylene chloride, dichloroethylene, carbon tetrachloride, trichlorethylene, etc., or aromatics such as benzene, toluene, xylene, monochlorobenzene, dichlorobenzene, etc. can be used. Coating can be carried out using a coating method such as a dip coating method, a spray coating method, a Meyer bar coating method, or a curtain coating method. For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying is generally preferably carried out at a temperature of 30° C. to 200° C. for a period of 5 minutes to 2 hours, either stationary or under ventilation. The charge transport layer of the present invention may contain various additives. For example, plasticizers such as diphenyl, m-terphenyl, and dibutyl phthalate, silicone oil, grafted silicone polymers, surface lubricants such as various fluorocarbons, dicyanovinyl compounds, potential stabilizers such as carbazole derivatives, β-carotene, and Ni complexes. ,
Examples include antioxidants such as 1,4-diazabicyclo[2,2,2]octane. The charge generating layer used in the present invention includes inorganic charge generating substances such as selenium, selenium-tellurium, amorphous silicon, pyrylium dyes, thiapyrylium dyes, azulenium dyes, thiacyanine dyes, quinocyanine dyes, azulenium dyes, etc. cationic dyes, squbarium salt dyes, phthalocyanine pigments, anthorone pigments, dibenzpyrenequinone pigments, polycyclic quinone pigments such as pyranthrone pigments, indigo pigments, quinacridone pigments, azo pigments, etc. Materials selected from the generated substances can be used alone or in combination as a vapor deposited layer or a coating layer. Among the charge generating substances used in the present invention,
There are a wide variety of azo pigments in particular, but typical structural examples of particularly effective azo pigments are shown below. As a general formula of an azo pigment, if we express the central skeleton as A and A(-N=N-Cp)n as the coupler part as Cp as shown below (where n
=2, or3), first, the following are specific examples of A:
【表】【table】
【表】【table】
【表】【table】
【表】
等が挙げられる。これら中心骨格A及びカプラー
Cpは適宜組合せにより電荷発生物質となる顔料
を形成する。
電荷発生層は、前述の電荷発生物質を適当な結
着剤に分散させ、これを支持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得ることができ
る。上記結着剤としては広範な絶縁性樹脂から選
択でき、また、ポリ−N−ビニルカルバゾール、
ポリビニルアントラセンやポリビニルピレンなど
の有機光導電性ポリマーから選択できる。好まし
くは、ポリビニルブチラール、ポリアクリレート
(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。塗工
の際に用いる有機溶剤としては、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
サノンなどのケトン類、N,N−ジメチルホルム
アミド,N,N−ジメチルアセトアミドなどのア
ミド類、ジメチルスルホキシドなどのスルホキシ
ド類、テトラヒドロフラン、ジオキサン、エチレ
ングリコールモノメチルエーテルなどのエーテル
類、酢酸メチル、酢酸エチルなどのエステル類、
クロロホルム、塩化メチレン、ジクロルエチレ
ン、四塩化炭素、トリクロルエチレンなどの脂肪
族ハロゲン化炭化水素類あるいはベンゼン、トル
エン、キシレン、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。
電荷発生層は、本発明になるチオエーテル化合
物を含有していてもかまわない。
電荷発生層は、十分な吸光度を得るために、で
きる限り多くの前記有機光導電体を含有し、且つ
発生した電荷キヤリアの寿命内にキヤリアを電荷
輸送層へ注入するために、薄膜層、例えば5μm以
下、好ましくは0.01μm〜1μmの膜厚をもつ薄膜
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
に帰因している。
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、導電性支持体の上に設けられ
る。導電性支持体としては、支持体自体が導電性
をもつもの、例えばアルミニウム、アルミニウム
合金、ステンレス、チタン、ニツケル、インジウ
ム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
法によつて被膜形成された層を有するプラスチツ
ク導電性粒子(例えば、アルミニウム粉末、酸化
チタン、酸化錫、酸化亜鉛、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支持体の上に被覆した支持
体、導電性粒子をプラスチツクや紙に含浸した支
持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。
導電性支持体と感光層の中間に、バリヤー機能
と接着機能をもつ下引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、0.1μm〜5μm、好ましくは
0.5μm〜3μmが適当である。
本発明の別の具体例では、前述のジスアゾ顔
料、あるいは米国特許第3554745号、同第3567438
号、同第3586500号公報などに開示のピリリウム
染料、チアピリリウム染料、セレナピリリウム染
料、ベンゾピリリウム染料、ベンゾチアピリリウ
ム染料、ナフトピリリウム染料、ナフトチアピリ
リウム染料などの光導電性を有する顔料や染料を
増感剤としても用いることができる。
また、別の具体例では、米国特許第3684502号
公報などに開示のピリリウム染料とアルキリデン
ジアリーレン部分を有する電気絶縁重合体との共
晶錯体を増感剤として用いることもできる。この
共晶錯体は、例えば4−〔4−ビス−(2−クロロ
エチル)アミノフエニル〕−2,6−ジフエニル
チアピリリウムパークロレートとポリ(4,4′−
イソプロピリデンジフエニレンカーボネート)を
ハロゲン化炭化水素系溶剤(例えば、ジクロルメ
タン、クロロホルム、四塩化炭素、1,1−ジク
ロルエタン、1,2−ジクロルルエタン、1,
1,2−トリクロエタン、クロルベンゼン、ブロ
モベンゼン、1,2−ジクロルベンゼン)に溶解
した後、これに非極性溶剤(例えば、ヘキサン、
オクタン、デカン、2,2,4−トリメチルベン
ゼン、リグロイン)を加えることによつて粒子状
共晶錯体として得られる。この具体例における電
子写真感光体には、スチレン−ブタジエンコポリ
マー、シリコン樹脂、ビニル樹脂、塩化ビニリデ
ン−アクリロニトリルコポリマー、スチレン−ア
クリロニトリルコポリマー、ビニルアセテート−
塩化ビニルコポリマー、ポリビニルブチラール、
ポリメチルメタクリレート、ポリ−N−ブチルメ
タクリレート、ポリエステル類、セルロースエス
テル類などを結着剤として含有することができ
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、
CRTプリンター、電子写真式製版システムなど
の電子写真応用分野にも広く用いることができ
る。
本発明によれば、高感度で、長期にわたる繰返
し帯電および露光を行つても電位変動の少ない電
子写真感光体を与えることができる。
以下、本発明を実施例に従つて説明する。
実施例1および比較例1〜2
下記構造式で示されるジスアゾ顔料5gをブチ
ラール樹脂(ブチラール化度70モル%)2gをシ
クロヘキサノン100mlに溶解した液とともにサン
ドミルで24時間分散し塗工液を調製した。
この塗工液をアルミシート上に乾燥膜厚が
0.2μmとなる様にマイヤーバーで塗布し電荷発生
層を形成した。
次に電荷輸送物質として前記例示化合物No.(13)10
gとポリカーボネート樹脂(平均分子量20000)
10gをモノクロルベンゼン70gに溶解し、この液
を先の電荷発生層の上にマイヤーバーで塗布し乾
燥膜厚が20μmの電荷輸送層を設け2層の電子写
真感光体を製造した。
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
いてスタチツク方式で−5KVでコロナ帯電し、
暗所で1秒間保持した後、照度20lux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(V1)を1/2に減衰するに
必要な露光量(E1/2)を測定した。
さらに、繰り返し使用した時の明部電位と暗部
電位の変動を測定するために、本実施例で作成し
た感光体をキヤノン(株)製PPC複写機NP−3525の
感光ドラム用シリンダーに貼り付けて、同機で
50000枚複写を行い、初期と5000枚および50000枚
複写後の明部電位(VL)及び暗部電位(VD)の
変動を測定した。
尚、初期のVDとVLは各々−700V、−200Vとな
る様に設定した。また比較の為に電荷輸送物質と
して前記例示化合物の代わりに下記構造式で示さ
れる化合物(A)および(B)を用いて、同様の感光体を
製造し、同様に測定を行つた。
(特開昭62−134652号公報記載の化合物)
この結果を第1表に示す。[Table] etc. These central skeletons A and couplers
Cp forms a pigment that becomes a charge-generating substance by appropriate combination. The charge-generating layer can be formed by dispersing the charge-generating substance described above in a suitable binder and coating it on a support, or by forming a vapor-deposited film using a vacuum evaporation device. You can get it by twisting it. The binder can be selected from a wide range of insulating resins, including poly-N-vinylcarbazole,
It can be selected from organic photoconductive polymers such as polyvinylanthracene and polyvinylpyrene. Preferably, polyvinyl butyral, polyacrylate (condensation polymer of bisphenol A and phthalic acid, etc.),
Examples include insulating resins such as polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyridine, cellulose resin, urethane resin, epoxy resin, casein, polyvinyl alcohol, and polyvinylpyrrolidone. . The resin contained in the charge generation layer is suitably 80% by weight or less, preferably 40% by weight or less. Organic solvents used during coating include alcohols such as methanol, ethanol and isopropanol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, dimethyl Sulfoxides such as sulfoxide, ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate,
Aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, trichloroethylene, etc., or aromatics such as benzene, toluene, xylene, monochlorobenzene, dichlorobenzene, etc. can be used. The charge generation layer may contain the thioether compound of the present invention. The charge generation layer contains as much of said organic photoconductor as possible in order to obtain sufficient absorbance and in order to inject carriers into the charge transport layer during the lifetime of the generated charge carriers, a thin film layer, e.g. It is preferable to form a thin film layer having a thickness of 5 μm or less, preferably 0.01 μm to 1 μm. 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. A photosensitive layer having such a laminated structure of a charge generation layer and a charge transport layer is provided on a conductive support. As the conductive support, materials that have conductivity themselves, such as aluminum, aluminum alloy, stainless steel, titanium, nickel, and indium, can be used. In addition, aluminum, aluminum alloy, indium oxide, tin oxide, Plastic conductive particles having a layer formed by vacuum deposition of indium oxide-tin oxide alloy, etc. (e.g., aluminum powder, titanium oxide, tin oxide, zinc oxide, carbon black, etc.)
A support obtained by coating plastic or the above-mentioned conductive support with silver particles (silver particles, etc.) together with a suitable binder, a support obtained by impregnating plastic or paper 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 support and the photosensitive layer.
The undercoat layer can be 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. It can be formed by twisting it. The thickness of the undercoat layer is 0.1 μm to 5 μm, preferably
0.5 μm to 3 μm is suitable. In another embodiment of the present invention, the disazo pigments described above, or U.S. Pat.
Pigments having photoconductivity such as pyrylium dyes, thiapyrylium dyes, selenapyrylium dyes, benzopyrylium dyes, benzothiapyryllium dyes, naphthopyryllium dyes, and naphthothiapyrylium dyes disclosed in the same publication No. 3586500, etc. Dyes can also be used as sensitizers. In another specific example, a eutectic complex of a pyrylium dye and an electrically insulating polymer having an alkylidene diarylene moiety, as disclosed in US Pat. No. 3,684,502, can also be used as a sensitizer. This eutectic complex is composed of, for example, 4-[4-bis-(2-chloroethyl)aminophenyl]-2,6-diphenylthiapyrylium perchlorate and poly(4,4'-
isopropylidene diphenylene carbonate) in a halogenated hydrocarbon solvent (e.g. dichloromethane, chloroform, carbon tetrachloride, 1,1-dichloroethane, 1,2-dichlorolethane, 1,
1,2-trichloroethane, chlorobenzene, bromobenzene, 1,2-dichlorobenzene) and then dissolved in a non-polar solvent (e.g. hexane,
It is obtained as a particulate eutectic complex by adding octane, decane, 2,2,4-trimethylbenzene, ligroin). The electrophotographic photoreceptor in this specific example includes styrene-butadiene copolymer, silicone resin, vinyl resin, vinylidene chloride-acrylonitrile copolymer, styrene-acrylonitrile copolymer, and vinyl acetate-copolymer.
vinyl chloride copolymer, polyvinyl butyral,
Polymethyl methacrylate, poly-N-butyl methacrylate, polyesters, cellulose esters, etc. can be contained as a binder. The electrophotographic photoreceptor of the present invention can be used not only for electrophotographic copying machines, but also for laser printers,
It can also be widely used in electrophotographic applications such as CRT printers and electrophotographic plate making systems. According to the present invention, it is possible to provide an electrophotographic photoreceptor that is highly sensitive and exhibits little potential fluctuation even after repeated charging and exposure over a long period of time. Hereinafter, the present invention will be explained according to examples. Example 1 and Comparative Examples 1 to 2 A coating solution was prepared by dispersing 5 g of a disazo pigment represented by the following structural formula in a sand mill for 24 hours with a solution of 2 g of butyral resin (degree of butyralization 70 mol%) dissolved in 100 ml of cyclohexanone. . Apply this coating solution on an aluminum sheet until the dry film thickness is
A charge generation layer was formed by coating with a Mayer bar to a thickness of 0.2 μm. Next, as a charge transport material, the above-mentioned exemplified compound No. (13) 10
g and polycarbonate resin (average molecular weight 20000)
10 g of the monochlorobenzene was dissolved in 70 g of monochlorobenzene, and this solution was applied onto the charge generation layer using a Mayer bar to form a charge transport layer having a dry thickness of 20 μm, thereby producing a two-layer electrophotographic photoreceptor. 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.
After holding it in a dark place for 1 second, it was exposed to light at an illuminance of 20 lux to examine the charging characteristics. As for the charging characteristics, the surface potential (Vo) and the exposure amount (E1/2) required to attenuate the potential ( V1 ) by 1/2 when dark decayed for 1 second were measured. Furthermore, in order to measure the fluctuations in bright area potential and dark area potential during repeated use, the photoreceptor prepared in this example was attached to the photosensitive drum cylinder of a PPC copier NP-3525 manufactured by Canon Inc. , on the same plane
50,000 sheets were copied, and the fluctuations in the bright area potential (V L ) and the dark area potential (V D ) at the initial stage, after 5,000 copies, and after 50,000 copies were measured. Note that the initial V D and V L were set to -700V and -200V, respectively. For comparison, similar photoreceptors were manufactured using compounds (A) and (B) represented by the following structural formulas in place of the above-mentioned exemplified compounds as charge transport materials, and measurements were performed in the same manner. (Compound described in JP-A-62-134652) The results are shown in Table 1.
【表】
第1表より明らかなように、本発明の化合物を
用いた感光体は、高感度で、かつ50000枚の耐久
テスト後も電位変動の少ない安定な感光体である
ことが判る。因みに、実施例1と比較例1および
2の感光体を50000枚耐久後、前述の複写機NP
−3525で初期と同一条件で画出し検討をしたとこ
ろ、実施例にはほとんど認められなかつたが、比
較例においては、かなりひどい地カブリが認めら
れた。
実施例2〜15および比較例3〜12
この各実施例においては、前記実施例1で用い
た電荷輸送物質として例示化合物(13)の代りに例示
化合物No.(1)(4)(5)(8)(11)(16)(18)(21)(25)(28
)(29)
(34)(35)(38)を用い、かつ電荷発生物質とし
て下記構造の顔料を用いたほかは、実施例1と同
様の方法によつて電子写真感光体を製造した。
各感光体の電子写真特性を実施例1と同様の方
法によつて測定した。その結果を次の第2表に示
す。また比較例として、電荷輸送物質として既知
のいくつかの化合物を用いて同様に製造した感光
体、および比較例2の化合物に10重量%で既知の
安定剤を加えて製造した感光体についても同様な
測定を行つた。その結果を第3表に示す。[Table] As is clear from Table 1, the photoreceptor using the compound of the present invention is highly sensitive and stable with little potential fluctuation even after a durability test of 50,000 sheets. Incidentally, after the photoconductors of Example 1 and Comparative Examples 1 and 2 were used for 50,000 sheets, the above-mentioned copying machine NP
-3525 under the same conditions as the initial stage, almost no fogging was observed in the examples, but quite severe background fogging was observed in the comparative examples. Examples 2 to 15 and Comparative Examples 3 to 12 In each of these Examples, Exemplified Compound No. (1) (4) (5) was used instead of Exemplified Compound (13) as the charge transport material used in Example 1. (8)(11)(16)(18)(21)(25)(28
) (29)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that (34), (35), and (38) were used, and a pigment having the structure shown below was used as the charge generating substance. The electrophotographic properties of each photoreceptor were measured in the same manner as in Example 1. The results are shown in Table 2 below. In addition, as comparative examples, photoreceptors manufactured in the same manner using several compounds known as charge transport materials, and photoreceptors manufactured by adding 10% by weight of a known stabilizer to the compound of Comparative Example 2 were also similarly prepared. We carried out measurements. The results are shown in Table 3.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
以上説明したように本発明になるチオエーテル
化合物を含有する電子写真感光体は高感度であ
り、また繰返し帯電、露光による連続画像形成に
際して明部電位と暗部電位の変動が小さい、耐久
性に優れた電子写真感光体を提供できるものであ
る。
As explained above, the electrophotographic photoreceptor containing a thioether compound according to the present invention has high sensitivity, and has excellent durability with small fluctuations in bright area potential and dark area potential during continuous image formation by repeated charging and exposure. It is possible to provide an electrophotographic photoreceptor.
Claims (1)
光体において、 該感光層が 一般式() 〔式中、R1およびR2は置換基を有してもよい
アルキル基、アラルキル基、アリール基または
R1とR2で結合して5ないし6員環を形成するの
に必要な残基を示す。Arは置換基を有してもよ
いアリーレン基または2価のヘテロ環基を示し、
nは0または1の整数を示す。Xは、S−R3ま
たは【式】を示し、YはS−R3、置換基を有 してもよいアルキル基、アラルキル基またはアリ
ール基を示し、あるいはXとYで結合してチオエ
ーテル環を形成するのに必要な残基を示す。R3
およびR4はR1およびR2と同義である。〕 で示されるチオエーテル化合物を含有することを
特徴とする電子写真感光体。 2 前記一般式()において、Arがフエニレ
ン基を示し、XおよびYが共にS−R3で示され
るチオエーテル構造であるか、または結合してチ
オエーテル構造を2ケ所有するチオエーテル環を
形成するのに必要な残基である特許請求の範囲第
1項記載の電子写真感光体。[Scope of Claims] 1. An electrophotographic photoreceptor having a photosensitive layer on a conductive support, wherein the photosensitive layer has the general formula () [In the formula, R 1 and R 2 are an alkyl group, an aralkyl group, an aryl group, which may have a substituent, or
Residues necessary for bonding R 1 and R 2 to form a 5- to 6-membered ring are shown. Ar represents an arylene group or a divalent heterocyclic group which may have a substituent,
n represents an integer of 0 or 1. X represents S-R 3 or [Formula], Y represents S-R 3 , an alkyl group, an aralkyl group, or an aryl group that may have a substituent, or X and Y combine to form a thioether ring. The residues necessary to form are shown. R3
and R 4 is synonymous with R 1 and R 2 . ] An electrophotographic photoreceptor comprising a thioether compound represented by the following. 2 In the general formula (), Ar represents a phenylene group, and X and Y both have a thioether structure represented by S-R 3 or combine to form a thioether ring having two thioether structures. The electrophotographic photoreceptor according to claim 1, which is a residue necessary for.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP29904587A JPH01140162A (en) | 1987-11-26 | 1987-11-26 | Electrophotographic sensitive body |
US07/274,503 US4931371A (en) | 1987-11-24 | 1988-11-21 | Electrophotographic photosensitive member |
FR8815260A FR2623638B1 (en) | 1987-11-24 | 1988-11-23 | IMPROVED PHOTOSENSITIVE ELECTROPHOTOGRAPHIC SUPPORT |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP29904587A JPH01140162A (en) | 1987-11-26 | 1987-11-26 | Electrophotographic sensitive body |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01140162A JPH01140162A (en) | 1989-06-01 |
JPH052983B2 true JPH052983B2 (en) | 1993-01-13 |
Family
ID=17867498
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP29904587A Granted JPH01140162A (en) | 1987-11-24 | 1987-11-26 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH01140162A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7452641B2 (en) | 2001-09-24 | 2008-11-18 | Samsung Electronics Co., Ltd. | Electrophotographic organophotoreceptors with novel charge transport compounds |
US6887634B2 (en) | 2001-09-24 | 2005-05-03 | Samsung Electronics Co., Ltd. | Electrophotographic organophotoreceptors with novel charge transport compounds |
JP3743718B2 (en) | 2002-11-14 | 2006-02-08 | 愛三工業株式会社 | Gas detector |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62134652A (en) * | 1985-12-06 | 1987-06-17 | Ricoh Co Ltd | Electrophotographic sensitive body |
-
1987
- 1987-11-26 JP JP29904587A patent/JPH01140162A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62134652A (en) * | 1985-12-06 | 1987-06-17 | Ricoh Co Ltd | Electrophotographic sensitive body |
Also Published As
Publication number | Publication date |
---|---|
JPH01140162A (en) | 1989-06-01 |
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