JPH02113258A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH02113258A JPH02113258A JP26672088A JP26672088A JPH02113258A JP H02113258 A JPH02113258 A JP H02113258A JP 26672088 A JP26672088 A JP 26672088A JP 26672088 A JP26672088 A JP 26672088A JP H02113258 A JPH02113258 A JP H02113258A
- Authority
- JP
- Japan
- Prior art keywords
- group
- charge
- formula
- aromatic ring
- general 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.)
- Granted
Links
- 239000000049 pigment Substances 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 45
- 239000000126 substance Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 22
- -1 styryl compound Chemical class 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 230000035945 sensitivity Effects 0.000 abstract description 17
- 239000000463 material Substances 0.000 abstract description 10
- 125000005504 styryl group Chemical group 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 230000003252 repetitive effect Effects 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 238000000576 coating method Methods 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000000460 chlorine Chemical group 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 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 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Chemical group 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-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
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920002382 photo conductive polymer Polymers 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000005427 anthranyl group Chemical group 0.000 description 2
- 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 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 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
- 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
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001230 polyarylate Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 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
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- QJNYIFMVIUOUSU-UHFFFAOYSA-N chloroethene;ethenyl acetate;furan-2,5-dione Chemical compound ClC=C.CC(=O)OC=C.O=C1OC(=O)C=C1 QJNYIFMVIUOUSU-UHFFFAOYSA-N 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 238000011156 evaluation Methods 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000007760 metering rod coating Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 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
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- VBJVZMAIULYQQB-UHFFFAOYSA-N propyl hypofluorite Chemical group CCCOF VBJVZMAIULYQQB-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
-
- 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
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
- G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
-
- 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
- G03G5/0683—Disazo dyes containing polymethine or anthraquinone groups
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電子写真感光体に関し、詳しくは電荷発生物質
を含有する電荷発生層と、電荷発生物質が発生したキャ
リアを受けとり、これを搬送する電荷輸送物質を含有す
る電荷輸送層を有する積層型電子写真感光体に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to an electrophotographic photoreceptor, and more specifically, a charge generation layer containing a charge generation substance and a carrier on which the charge generation substance has been generated are received and transported. The present invention relates to a laminated electrophotographic photoreceptor having a charge transport layer containing a charge transport material.
このような有機感光体としては、ポリ−N−ビニルカル
バゾールに代表される光導電性ポリマー及びこれと2.
4.7−ドリニトロー9−フルオレノン等のルイス酸と
から形成される電荷移動錯体を主成分とする感光層を有
する電子写真感光体はすでに実用化されている。しかし
、この感光体は、感度および耐久性において必ずしも満
足できるものではない。Such organic photoreceptors include photoconductive polymers typified by poly-N-vinylcarbazole and 2.
Electrophotographic photoreceptors having a photosensitive layer mainly composed of a charge transfer complex formed from a Lewis acid such as 4,7-dolinitro-9-fluorenone have already been put to practical use. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability.
一方、電荷発生機能と電荷輸送機能とをそれぞれ別個の
物質に分担させた機能分離型電子写真感光体が、従来の
有機感光体の欠点とされていた感度や耐久性に著しい改
善をもたらした。このような機能分離型感光体は、電荷
発生物質、電荷輸送物質の各々の材料選択範囲が広く、
任意の特性を有する電子写真感光体を比較的容易に作製
し得るという利点を有している。特に電子写真感光体が
複写機のみならず、近年ではレーザービームプリンター
LEDプリンター等に用いられるようになるにつれ、
使用する光源の発光波長に合った分光感度域を設定する
ためには機能分離型が適している。On the other hand, functionally separated electrophotographic photoreceptors, in which charge generation and charge transport functions are performed by separate materials, have brought about significant improvements in sensitivity and durability, which were considered to be shortcomings of conventional organic photoreceptors. Such a functionally separated photoreceptor has a wide range of materials to choose from for charge-generating substances and charge-transporting substances.
This method has the advantage that an electrophotographic photoreceptor having arbitrary characteristics can be produced relatively easily. In particular, as electrophotographic photoreceptors have come to be used not only in copiers but also in laser beam printers, LED printers, etc. in recent years,
A functionally separated type is suitable for setting a spectral sensitivity range that matches the emission wavelength of the light source used.
電荷発生物質としては、種々のアゾ顔料、フタロシアニ
ン顔料、多環キノン顔料、シアニン色素スクエアリック
酸染料、ピリリウム塩系色素等が知られている。中でも
アゾ顔料は耐光性が強い、電荷発生能力が大きい、材料
合成が容易等の点から多くの構造が提唱されてきた。例
えば本発明に類似のジスアゾ顔料として特開昭56−1
16040号公報、特開昭57−182747号公報、
特開昭58−49952号公報、特開昭58−1154
47号公報、特開昭59−72448号公報、特開昭5
9−155848号公報。As charge generating substances, various azo pigments, phthalocyanine pigments, polycyclic quinone pigments, cyanine dyes, squaric acid dyes, pyrylium salt dyes, and the like are known. Among them, many structures have been proposed for azo pigments because of their strong light resistance, large charge generation ability, and ease of material synthesis. For example, as a disazo pigment similar to the present invention, JP-A-56-1
No. 16040, JP-A-57-182747,
JP-A-58-49952, JP-A-58-1154
No. 47, JP-A-59-72448, JP-A-Sho 5
Publication No. 9-155848.
特開昭58−115445号公報、特開昭58−115
446号公報、特開昭59−7365号公報等がすでに
公知である。ここで電荷発生物質として用いられるアゾ
顔料に要求されることは(i)熱・光に対して安定であ
ること、(it )分離状態で電荷発生能を示すもので
は、分散が容易であること及び分散液の経時変化の少な
いこと、(iii )電荷発生能が温度により変化しな
いこと、(iv )繰り返し使用時において特性の変化
のないこと、(V)用いる光源に対して有効な分光感度
域をもっていること、(vi )電荷輸送物質が限定さ
れないこと等があげられる。これらの要求を高いレベル
で平均的に満足することが実用上量も重要なことである
。前述の公知顔料の中には上記要求の一部は満足するも
ののすべてを高いレベルで満足するものはなかった。JP-A-58-115445, JP-A-58-115
446, Japanese Unexamined Patent Publication No. 59-7365, etc. are already known. The azo pigment used here as a charge-generating substance is required to (i) be stable against heat and light, and (it) be easy to disperse if it exhibits charge-generating ability in a separated state. and (iii) the charge generation ability does not change with temperature, (iv) the characteristics do not change during repeated use, (V) the spectral sensitivity range is effective for the light source used. and (vi) the charge transport substance is not limited. In practical terms, it is important to satisfy these requirements at a high level on average. Although some of the above-mentioned known pigments satisfy some of the above requirements, none satisfy all of them to a high level.
一方、電荷輸送物質としては、ヒドラゾン化合物、ピラ
ゾリン化合物、スチルベン化合物、トリアリールメタン
化合物、アリールアミン化合物等が知られている。これ
らの化合物に要求されることは(i)光・熱に対して安
定であること、(it)コロナ放電により発生するオゾ
ン、NO,、硝酸等に対して安定であること、(iff
)高い輸送能を示すこと、(iv )有機溶剤結着剤と
の相溶性が高いこと等があげられる。On the other hand, hydrazone compounds, pyrazoline compounds, stilbene compounds, triarylmethane compounds, arylamine compounds, and the like are known as charge transport substances. These compounds are required to (i) be stable against light and heat, (it) be stable against ozone, NO, nitric acid, etc. generated by corona discharge, and (if
) exhibiting high transport ability; and (iv) exhibiting high compatibility with organic solvent binders.
前述の公知アゾ顔料と電荷輸送物質との組合わせとして
は例えば、特開昭58−18636号公報。An example of the combination of the above-mentioned known azo pigment and a charge transport substance is disclosed in JP-A-58-18636.
特開昭57−204551号公報、特開昭59−440
50号公報、特開昭59−44051号公報、特開昭5
9−157644号公報、特開昭60−24549号公
報、特開昭60−24550号公報、特開昭60−24
551号公報、特開昭60−24552号公報等があげ
られる。JP-A-57-204551, JP-A-59-440
No. 50, JP-A-59-44051, JP-A-5
9-157644, JP 60-24549, JP 60-24550, JP 60-24
551, JP-A-60-24552, and the like.
これらの組合わせによる感光体は、繰返し使用時におけ
る電位変動は少ないものの、使用環境の変化による画像
の劣化がみられる等、画像特性上大きな欠点を有するも
のが多(、実際の使用上問題となっている。Although photoreceptors made with these combinations have little potential fluctuation during repeated use, they often have major drawbacks in image characteristics, such as image deterioration due to changes in the usage environment (this is a problem in actual use). It has become.
本発明の目的は、電荷発生層と電荷輸送層とを有する機
能分離型感光体において、大きな感度を有し、しかも繰
返し使用時の電位が安定に維持され、かつ使用環境(温
度、湿度)によらず安定した感度と画像特性を示すこと
のできる電子写真感光体を提供することである。An object of the present invention is to provide a functionally separated photoreceptor having a charge generation layer and a charge transport layer, which has high sensitivity, maintains a stable potential during repeated use, and is compatible with the usage environment (temperature, humidity). An object of the present invention is to provide an electrophotographic photoreceptor that can exhibit stable sensitivity and image characteristics regardless of fluctuation.
また、本発明の目的は、アゾ顔料の分散が容易でしかも
分散液の経時変化の少ないアゾ顔料を提供することであ
る。Another object of the present invention is to provide an azo pigment which can be easily dispersed and whose dispersion liquid changes little over time.
また、本発明の目的は、600から700nmの領域の
光源に対して、十分大きな感度を示す電子写真感光体を
提供することである。Another object of the present invention is to provide an electrophotographic photoreceptor that exhibits sufficiently high sensitivity to light sources in the range of 600 to 700 nm.
また、本発明の目的は、コロナ放電により発生するオゾ
ン、No、、硝酸等に対して安定な感光体を提供するこ
とにある。Another object of the present invention is to provide a photoreceptor that is stable against ozone, NO, nitric acid, etc. generated by corona discharge.
本発明者らの検討の結果、特定構造のジスアゾ顔料を含
有する電荷発生層と特定構造のスチリル化合物を含有す
る電荷輸送層とを有する積層型電子写真感光体が、前記
問題点を解決し優れた電子写真特性を示すことを見い出
した。As a result of studies by the present inventors, a laminated electrophotographic photoreceptor having a charge generation layer containing a disazo pigment with a specific structure and a charge transport layer containing a styryl compound with a specific structure solves the above problems and is superior. It was discovered that the electrophotographic properties of
すなわち本発明は、導電性支持体上に電荷発生層と電荷
輸送層を有する積層型電子写真感光体において、電荷発
生層は電荷発生物質として、一般式(1)
一般式(3)
で示されるジスアゾ顔料を含有し、電荷輸送層は電荷輸
送物質として、
一般式(2)
で示されるスチリ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。That is, the present invention provides a laminated electrophotographic photoreceptor having a charge generation layer and a charge transport layer on a conductive support, in which the charge generation layer is a charge generation substance represented by the general formula (1) or the general formula (3). The electrophotographic photoreceptor is characterized in that it contains a disazo pigment, and the charge transport layer contains a styryl compound represented by the general formula (2) as a charge transport substance.
一般式(1)中、R1およびR2は、アルキル基。In general formula (1), R1 and R2 are alkyl groups.
アラルキル基、芳香環基または複素環基を示し、具体的
にはメチル、エチル、プロピル、ブチル等のアルキル基
、ベンジル、フェネチル、ナフチルメチル等のアラルキ
ル基、フェニル、ジフェニル。It represents an aralkyl group, an aromatic ring group, or a heterocyclic group, specifically an alkyl group such as methyl, ethyl, propyl, butyl, an aralkyl group such as benzyl, phenethyl, or naphthylmethyl, phenyl, or diphenyl.
ナフチル、アンスリル等の芳香環基および、カルバゾー
ル、ジベンゾフラン、ベンズイミダシロン。Aromatic ring groups such as naphthyl and anthryl, and carbazole, dibenzofuran, and benzimidacylon.
ベンズチアゾール、チアゾール、ピリジン等の複素環基
が挙げられる。Examples include heterocyclic groups such as benzthiazole, thiazole, and pyridine.
また、これらのアルキル基、アラルキル基、アリール基
、芳香環基および複素環基は例えばメチル、エチル、プ
ロピル等のアルキル基、またはメトキシ、エトキシ、プ
ロポキシ等のアルコキシ基、フッ素、塩素、臭素等のハ
ロゲン原子またはニトロ基、シアノ基、トリフルオロメ
チル基等の置換基を有してもよい。ArIおよびAr2
は芳香環基または複素環基を示し、これらの芳香環基お
よび複素環基の具体例は前記と同じである。また、これ
らの芳香環基、複素環基は置換基を有してもよく、例え
ば前途のような、アルキル基、アルコキシ基。In addition, these alkyl groups, aralkyl groups, aryl groups, aromatic ring groups and heterocyclic groups include, for example, alkyl groups such as methyl, ethyl, and propyl, or alkoxy groups such as methoxy, ethoxy, and propoxy, and fluorine, chlorine, and bromine groups. It may have a halogen atom or a substituent such as a nitro group, a cyano group, or a trifluoromethyl group. ArI and Ar2
represents an aromatic ring group or a heterocyclic group, and specific examples of these aromatic ring groups and heterocyclic groups are the same as above. Further, these aromatic ring groups and heterocyclic groups may have a substituent, such as an alkyl group or an alkoxy group as mentioned above.
ハロゲン原子またはシアノ基等が挙げられる。Examples include a halogen atom and a cyano group.
X、、X2.X3およびX4は水素原子、メチル、エチ
ル、プロピル等のアルキル基、メトキシ。X,,X2. X3 and X4 are hydrogen atoms, alkyl groups such as methyl, ethyl, propyl, and methoxy.
エトキシ、プロポキシ等のアルコキシ基、ハロゲン原子
、ニトロ基、シアノ基、又はトリフルオロメチル基を示
し、全てが水素原子であることはない。It represents an alkoxy group such as ethoxy or propoxy, a halogen atom, a nitro group, a cyano group, or a trifluoromethyl group, and not all of them are hydrogen atoms.
Zは酸素原子又は硫黄原子を示す。Z represents an oxygen atom or a sulfur atom.
一般式(2)および一般式(3)中、R3およびR4は
、アルキル基、アラルキル基、芳香環基または複素環基
を示し、具体的には、メチル、エチル。In the general formulas (2) and (3), R3 and R4 represent an alkyl group, an aralkyl group, an aromatic ring group, or a heterocyclic group, and specifically, methyl and ethyl.
プロピル、ブチル等のアルキル基、ベンジル、フェネチ
ル、ナフチルメチル等のアラルキル基、フェニル、ジフ
ェニル、ナフチル、アンスリル等の芳香環基またはピリ
ジル、キノリル、チエニル、フリル等の複素環基を示す
。またこれらのアルキル基、アラルキル基、芳香環基お
よび複素環基は置換基を有していてもよ(、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、
フッ素、塩素、臭素等のハロゲン原子またはニトロ基等
が挙げられる。It represents alkyl groups such as propyl and butyl, aralkyl groups such as benzyl, phenethyl and naphthylmethyl, aromatic ring groups such as phenyl, diphenyl, naphthyl and anthryl, and heterocyclic groups such as pyridyl, quinolyl, thienyl and furyl. Furthermore, these alkyl groups, aralkyl groups, aromatic ring groups and heterocyclic groups may have substituents (for example, alkyl groups such as methyl, ethyl, propyl, methoxy, ethoxy, propoxy, etc.). alkoxy group,
Examples include halogen atoms such as fluorine, chlorine, and bromine, and nitro groups.
R6およびR8は水素原子、アルキル基、アルコキシ基
またはハロゲン原子を示す。アルキル基およびアルコキ
シ基の具体例は前記と同じである。R6 and R8 represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom. Specific examples of the alkyl group and alkoxy group are the same as above.
またアルキル基およびアルコキシ基は前記のような置換
基を有していてもよい。Further, the alkyl group and alkoxy group may have the above-mentioned substituents.
Ar3は芳香環基または複素環基を示し、具体的には、
フェニル、ナフチル等の芳香環基またはピリジル、キノ
リル、チエニル、フリル等の複素環基を示す。芳香環基
および複素環基は置換基を有していてもよい。このAr
3が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、フッ素、塩素、臭素等のハ
ロゲン原子またはニトロ基などが挙げられる。Ar3 represents an aromatic ring group or a heterocyclic group, specifically,
Indicates aromatic ring groups such as phenyl and naphthyl, or heterocyclic groups such as pyridyl, quinolyl, thienyl, and furyl. The aromatic ring group and the heterocyclic group may have a substituent. This Ar
Examples of substituents that 3 may have include alkyl groups such as methyl, ethyl, and propyl, alkoxy groups such as methoxy, ethoxy, and propoxy, halogen atoms such as fluorine, chlorine, and bromine, and nitro groups.
一般式(3)中、Yは単結合、−CH2CH2−または
−CH=CH−を示す。In general formula (3), Y represents a single bond, -CH2CH2- or -CH=CH-.
さらに前記電荷発生物質の中でも一般式(4)で示され
る構造のジスアゾ顔料は電子写真特性上特に優れるもの
である。Further, among the charge-generating substances, the disazo pigment having the structure represented by the general formula (4) is particularly excellent in terms of electrophotographic properties.
一般式(4)
一般式(4)中、R7およびR8は水素原子、メチル、
エチル、プロピル等のアルキル基、ベンジル。General formula (4) In general formula (4), R7 and R8 are hydrogen atoms, methyl,
Alkyl groups such as ethyl and propyl, benzyl.
フェネチル、ナフチルメチル等のアラルキル基、フェニ
ル、ナフチル、アンスラニル等の芳香環基、メトキシ、
エトキシ、プロポキシ等のアルコキシ基、フッ素、塩素
、臭素等のハロゲン原子、ニトロ基、シアノ基、トリフ
ルオロメチル基を示す。Aralkyl groups such as phenethyl and naphthylmethyl, aromatic ring groups such as phenyl, naphthyl and anthranyl, methoxy,
Indicates an alkoxy group such as ethoxy or propoxy, a halogen atom such as fluorine, chlorine, or bromine, a nitro group, a cyano group, or a trifluoromethyl group.
R8およびR8゜は水素原子、メチル、エチル。R8 and R8° are hydrogen atoms, methyl, and ethyl.
プロピル等のアルキル基、ベンジル、フェネチル。Alkyl groups such as propyl, benzyl, phenethyl.
ナフチルメチル等のアラルキル基、フェニル、ナフチル
、アンスラニル等の芳香環基、メトキシ。Aralkyl groups such as naphthylmethyl, aromatic ring groups such as phenyl, naphthyl, anthranyl, and methoxy.
エトキシ、プロポキシ等のアルコキシ基、フッ素。Alkoxy groups such as ethoxy and propoxy, fluorine.
塩素、臭素等のハロゲン原子、シアノ基またはトリフル
オロメチル基を示し、R7,R8,RoおよびRtoの
アルキル基、芳香環基、アラルキル基。A halogen atom such as chlorine or bromine, a cyano group or a trifluoromethyl group, and an alkyl group, aromatic ring group, or aralkyl group for R7, R8, Ro and Rto.
およびアルコキシ基は置換基を有していてもよ(、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、フッ素、塩
素、臭素等のハロゲン原子、ニトロ基、シアノ基または
トリフルオロメチル基等がある。and alkoxy groups may have substituents (for example, alkyl groups such as methyl, ethyl, propyl, alkoxy groups such as methoxy, ethoxy, propoxy, halogen atoms such as fluorine, chlorine, bromine, nitro groups, cyano group or trifluoromethyl group.
z、Xl、X2.X3およびX4は一般式(1)と同じ
意味を示す。z, Xl, X2. X3 and X4 have the same meaning as in general formula (1).
以下に本発明に用いられる電荷発生物質と電荷輸送物質
の代表例を挙げる。Representative examples of charge generating substances and charge transporting substances used in the present invention are listed below.
電荷発生物質
G−2
G−13
G−14
I
r
G−詔
G−あ
G−37
G−羽
ト
G−49
G−50
G−聞
しE
I
G−絽
α
しI
C!
G−61
G−62
CF3
G−邸
α
G−73
G−74
へり2
Nυ2
G−86
G−91
G−97
G−98
+04
+05
し215
し2H5
f
(I
l
UILII s
G−121
G−122
G−I S旧
It
CI!
電荷輸送物質
しl−13
T−62
T−63
以下に本発明の電子写真感光体を図面を用いて説明する
。Charge-generating substance G-2 G-13 G-14 I r G-Emperor G-A G-37 G-Hato G-49 G-50 G-Toshi E I G-絽α しIC! G-61 G-62 CF3 G-tei α G-73 G-74 Edge 2 Nυ2 G-86 G-91 G-97 G-98 +04 +05 Shi215 Shi2H5 f (I l UILII s G-121 G-122 GI S Former It CI! Charge Transport Material 1-13 T-62 T-63 The electrophotographic photoreceptor of the present invention will be described below with reference to the drawings.
第1図は本発明の電子写真感光体の層構成を模式的に表
わした図である。FIG. 1 is a diagram schematically showing the layer structure of the electrophotographic photoreceptor of the present invention.
一般式(1)で示されるジスアゾ顔料を含有する電荷発
生層2は、十分な吸光度を得るために、できる限り多(
の前述の光導電性を示す化合物を含有し、且つ発生した
電荷キャリアの飛程を短くするために薄膜層、例えば5
μm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。The charge generation layer 2 containing the disazo pigment represented by the general formula (1) should contain as much (
containing the above-mentioned photoconductive compound and a thin film layer, e.g.
It is preferable to form a thin film layer having a thickness of 1 μm or less, preferably 0.01 μm to 1 μm.
電荷発生層2は、前述のジスアゾ顔料を適当なバインダ
ーに分散させ、これを支持体の上に塗工することによっ
て形成でき、また真空蒸着装置により蒸着膜を形成する
ことによって得ることができる。電荷発生層を塗工によ
って形成する際に用いつるバインダーとしては広範な絶
縁性樹脂から選択でき、またポリ−N−ビニルカルバゾ
ール、ポリビニルアントラセンやポリビニルピレンなど
の有機光導電性ポリマーから選択できる。好ましくは、
ポリビニルブチラール、ボリアリレート(ビスフェノー
ルAとフタル酸の縮重合体など)、ポリカーボネート、
ポリエステル、フェノキシ樹脂、ポリ酢酸ビニル、アク
リル樹脂、ポリアクリルアミド樹脂、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。The charge generating layer 2 can be formed by dispersing the above-mentioned disazo pigment in a suitable binder and coating it on a support, or can be obtained by forming a vapor deposited film using a vacuum vapor deposition apparatus. The binder used in forming the charge generating layer by coating can be selected from a wide variety of insulating resins and organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene and polyvinylpyrene. Preferably,
Polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.), polycarbonate,
Examples include insulating resins such as 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 80% by weight or less,
A suitable amount is preferably 40% by weight or less.
これらの樹脂を溶解する溶剤は、樹脂の種類によって異
なり、また下達の電荷輸送層や下引層を溶解しないもの
から選択することが好ましい。The solvent that dissolves these resins varies depending on the type of resin, and is preferably selected from those that do not dissolve the underlying charge transport layer or subbing layer.
具体的な有機溶剤としては、メタノール、エタノール、
イソプロパツールなどのアルコール類、アセトン、メチ
ルエチルケトン、シクロヘキサノンなどのケトン類、N
、N−ジメチルホルムアミドlNlN−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
レングリコールモツメチルエーテルなどのエーテル類、
酢酸メチル。Specific organic solvents include methanol, ethanol,
Alcohols such as isopropanol, ketones such as acetone, methyl ethyl ketone, cyclohexanone, N
, amides such as N-dimethylformamide 1N1N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide, ethers such as tetrahydrofuran, dioxane, ethylene glycol motumethyl ether,
Methyl acetate.
酢酸エチルなどのエステル類、クロロホルム、塩化メチ
レン、ジクロルエチレン、四塩化炭素、トリクロルエチ
レンなどの脂肪族ハロゲン化炭化水素類あるいはベンゼ
ン、トルエン、キシレン、リグロイン、モノクロルベン
ゼン、ジクロルベンゼンなどの芳香族類などを用いるこ
とができる。Esters such as ethyl acetate, aliphatic halogenated hydrocarbons such as chloroform, methylene chloride, dichloroethylene, carbon tetrachloride, trichloroethylene, or aromatic compounds such as benzene, toluene, xylene, ligroin, monochlorobenzene, dichlorobenzene etc. can be used.
塗工は、浸漬コーティング法、スプレーコーティング法
、マイヤーバーコーティング法、ブレードコーティング
法などのコーティング法を用いて行うことができる。乾
燥は室温における指触乾燥後、加熱乾燥する方法が好ま
しい。加熱乾燥は、30℃〜200℃の温度で5分〜2
時間の範囲の時間で、静止または送風下で行うことがで
きる。Coating can be performed using a coating method such as a dip coating method, a spray coating method, a Meyer bar coating method, or a blade coating method. For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying at a temperature of 30°C to 200°C for 5 minutes to 2
It can be done stationary or under a draft for a range of hours.
電荷輸送層3は、前述の電荷発生層2と電気的に接続さ
れており、電界の存在下で電荷発生層から注入された電
荷キャリアを受は取るとともに、これらの電荷キャリア
を表面まで輸送できる機能を有している。この際、この
電荷輸送層3は、電荷発生層2の上に積層されているの
が好ましいが、電荷輸送層3は電荷発生層2の下に積層
されていてもよい。The charge transport layer 3 is electrically connected to the charge generation layer 2 described above, and is capable of receiving and receiving charge carriers injected from the charge generation layer in the presence of an electric field and transporting these charge carriers to the surface. It has a function. At this time, the charge transport layer 3 is preferably laminated on the charge generation layer 2, but the charge transport layer 3 may be laminated below the charge generation layer 2.
電荷輸送層3は前述の電荷輸送物質を適当なバインダー
と共に溶解塗布し形成することができる。The charge transport layer 3 can be formed by dissolving and coating the charge transport material described above together with a suitable binder.
バインダーとして使用できる樹脂は、例えばアクリル樹
脂、ボリアリレート、ポリエステル、ポリカーボネート
、ポリスチレン、アクリロニトリル−スチレンコポリマ
ー、アクリロニトリル−ブタジェンコポリマー、ポリビ
ニルブチラール、ポリビニルホルマール、ポリスルホン
、ポリアクリルアミド、ポリアミド、塩素化ゴムなどの
絶縁性樹脂、あるいはポリ−N−ビニルカルバゾール、
ポリビニルアントラセン、ポリビニルピレンなどの有機
光導電性ポリマーを挙げることができる。Resins that can be used as binders include, for example, acrylic resins, polyarylates, polyesters, polycarbonates, polystyrene, acrylonitrile-styrene copolymers, acrylonitrile-butadiene copolymers, polyvinyl butyral, polyvinyl formal, polysulfones, polyacrylamides, polyamides, chlorinated rubbers, etc. resin, or poly-N-vinylcarbazole,
Mention may be made of organic photoconductive polymers such as polyvinylanthracene and polyvinylpyrene.
電荷輸送層3は、電荷キャリアを輸送できる限界がある
ので、必要以上に膜厚を厚くすることができない。−船
釣には、5μm〜35μmであるが、好ましい範囲は8
μm〜30μmである。塗工によって電荷輸送層を形成
する際には、前述した様な適当なコーティング法を用い
ることができる。Since the charge transport layer 3 has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary. - For boat fishing, the range is 5 μm to 35 μm, but the preferred range is 8 μm.
It is μm to 30 μm. When forming the charge transport layer by coating, an appropriate coating method as described above can be used.
この様な電荷発生層2と電荷輸送層3の積層構造からな
る感光層4は、導電性支持体1の上に設けられる。導電
性支持体1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って被膜形成された
層を有するプラスチック、導電性粒子(例えば、カーボ
ンブラック、銀粒子など)を適当なバインダーとともに
プラスチックや前記金属支持体の上に被覆した支持体、
導電性粒子をプラスチッ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ックなどを用いることがで
きる。A photosensitive layer 4 having such a laminated structure of the charge generation layer 2 and the charge transport layer 3 is provided on the conductive support 1 . As the conductive support 1, the support itself is conductive;
For example, aluminum, aluminum alloy, stainless steel, etc. can be used, and in addition, plastics having a layer formed by vacuum evaporation of aluminum, aluminum alloy, indium oxide, tin oxide, indium oxide-tin oxide alloy, etc., conductive A support in which particles (e.g., carbon black, silver particles, etc.) are coated on a plastic or metal support with a suitable binder;
A support made of plastic or paper impregnated with conductive particles, a plastic containing a conductive polymer, etc. can be used.
導電性支持体1と感光層4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。A subbing layer having a barrier function and an adhesive function can also be provided between the conductive support 1 and the photosensitive layer 4.
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って形成
できる。The subbing layer can be formed from 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. .
下引層の膜厚は、0.1μm〜5μm、好ましくは0.
5μm〜3μmが適当である。The thickness of the undercoat layer is 0.1 μm to 5 μm, preferably 0.1 μm to 5 μm.
A suitable thickness is 5 μm to 3 μm.
本発明の電子写真感光体は電子写真複写機に利用するの
みならずレーザープリンターやLEDプリンター、液晶
プリンター、レーザー製版等の電子写真応用分野にも広
(利用できるが特にLEDプリンターに用いることで性
能を十分に発現させることができる。The electrophotographic photoreceptor of the present invention can be used not only in electrophotographic copying machines, but also in electrophotographic application fields such as laser printers, LED printers, liquid crystal printers, and laser plate making. can be fully expressed.
以下本発明を実施例によって説明する。 The present invention will be explained below with reference to Examples.
実施例1
アルミ板上に0.1μmの塩化ビニル−無水マレイン酸
−酢酸ビニル共重合体樹脂よりなる下引層を設けた。Example 1 A 0.1 μm undercoat layer made of vinyl chloride-maleic anhydride-vinyl acetate copolymer resin was provided on an aluminum plate.
次に前記例示のジスアゾ顔料(G−13)5gをシクロ
へキサノン95m1にブチラール樹脂(ブチラール化度
63モル%、数平均分子量20000) 2gを溶かし
た液に加えサンドミルで20時間分散した。Next, 5 g of the above-exemplified disazo pigment (G-13) was added to a solution in which 2 g of butyral resin (degree of butyralization 63 mol%, number average molecular weight 20,000) was dissolved in 95 ml of cyclohexanone, and dispersed in a sand mill for 20 hours.
この分散液を先に形成した下引層の上に乾燥後の膜厚が
0.5μmとなるようにマイヤーバーで塗布し乾燥して
電荷発生層を形成した。This dispersion was applied onto the previously formed undercoat layer using a Mayer bar so that the film thickness after drying was 0.5 μm, and dried to form a charge generation layer.
次いで、前記例示のスチリル化合物(T−39)5gと
ビスフェノール2型ポリカーボネート樹脂(粘度平均分
子量30000) 5gをクロルベンゼン70m1に溶
解し、これを電荷発生層の上に乾燥後の膜厚が22μm
となるようにマイヤーバー塗布し乾燥して電荷輸送層を
形成し感光体No、1を作製した。Next, 5 g of the above-exemplified styryl compound (T-39) and 5 g of bisphenol 2 type polycarbonate resin (viscosity average molecular weight 30,000) were dissolved in 70 ml of chlorobenzene, and this was applied onto the charge generation layer so that the film thickness after drying was 22 μm.
A charge transport layer was formed by applying a Mayer bar and drying to prepare photoreceptor No. 1.
この様にして作製した電子写真感光体を川口電機■製静
電複写紙試験装置Model 5P−428を用いて
スタティック方式で−5,5KVのコロナ帯電し、暗所
で1時間保持した後、照度2j’uxのハロゲンランプ
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(VD)をAに
減衰するに必要な露光量(6%)を測定した。The electrophotographic photoreceptor thus prepared was statically charged with a corona charge of -5.5 KV using an electrostatic copying paper tester Model 5P-428 manufactured by Kawaguchi Denki, and after being kept in a dark place for 1 hour, the illuminance was It was exposed to light using a 2j'ux halogen lamp and its charging characteristics were examined. As for the charging characteristics, the surface potential (vo) and the exposure amount (6%) required to attenuate the potential (VD) to A when dark decayed for 1 second were measured.
結果を以下に示す。The results are shown below.
V o : 720V
V D : −700V
E’4 : 0.99 lux e sec次に、先
の静電複写紙試験装置の光源に光強度lμW / c
rdの単色光を用い分光感度を測定した。Vo: 720V VD: -700V E'4: 0.99 lux e sec Next, the light intensity of lμW/c was applied to the light source of the electrostatic copy paper tester.
Spectral sensitivity was measured using rd monochromatic light.
感度は表面電位(VO)を−700vとし表面電位が−
200Vになるのに要する露光量EΔ6oov(μJ/
Crrr)を測定し、
を計算し、波長に対しプロットした結果を第2図に示す
。Sensitivity is when the surface potential (VO) is -700v and the surface potential is -
Exposure amount required to reach 200V EΔ6oov (μJ/
Crrr) was measured, Crrr was calculated, and plotted against wavelength, the results are shown in FIG.
さらに本感光体を−5,6KVのコロナ帯電器、露光光
学系、現像機、転写帯電器、除電露光光学系およびクリ
ーナーを備えた電子写真複写機のシリンダーに貼り付は
画像特性を調べた。この複写機はシリンダーの駆動に伴
い転写紙上に画像が得られる構成になっている。この複
写機を用いた画像特性の評価は湿度10%気温5℃、湿
度50%気温18℃、湿度80%気温35℃の三環境に
て行った。Furthermore, this photoreceptor was attached to the cylinder of an electrophotographic copying machine equipped with a -5.6 KV corona charger, an exposure optical system, a developing device, a transfer charger, a static elimination exposure optical system, and a cleaner, and its image characteristics were examined. This copying machine is configured to produce an image on transfer paper as a cylinder is driven. Image characteristics using this copying machine were evaluated in three environments: humidity 10% temperature 5°C, humidity 50% temperature 18°C, and humidity 80% temperature 35°C.
いずれの環境においてもオリジナルに忠実な良好な画像
が得られた。この画像は1万枚目においても画像のにじ
み、ボケ等はみられず本感光体が良好な画像特性を示す
ことがわかった。Good images faithful to the original were obtained in both environments. Even after the 10,000th print, no blurring or blurring of the image was observed, indicating that the present photoreceptor exhibited good image characteristics.
実施例2
実施例1のジスアゾ顔料(G−13)にかえて、ジスア
ゾ顔料G−10,G−11,G−19およびG−14を
それぞれ用いる以外は実施例1と全く同様にして感光体
を作製し帯電特性と分光感度を測定した。帯電特性を第
1表に、分光感度を第3図に示す。Example 2 A photoreceptor was prepared in the same manner as in Example 1 except that disazo pigments G-10, G-11, G-19 and G-14 were used in place of the disazo pigment (G-13) in Example 1. We fabricated and measured the charging characteristics and spectral sensitivity. Charging characteristics are shown in Table 1, and spectral sensitivity is shown in Figure 3.
第1表
実施例感光体No、 ジスアゾ顔料 Vo (V)
Vo (V) E!4 (j! ux−sec)2
2 G−10−720−6901,3
433G−11−740−7042,1144G−14
−700−6501,5555G−19−700−68
00,90比較例1および2
特開昭59−157644号公報記載の下記比較ジスア
ゾ顔料(1)
比較顔料(1)
を用いる以外は実施例1と全く同様にして感光体を作製
し比較試料lとし実施例1と同様にして帯電特性を調べ
た。さらに下記構造の比較顔料(2)についても同様の
評価を行った。Table 1 Example photoreceptor No. Disazo pigment Vo (V)
Vo (V) E! 4 (j!ux-sec)2
2 G-10-720-6901,3
433G-11-740-7042, 1144G-14
-700-6501, 5555G-19-700-68
00,90 Comparative Examples 1 and 2 A photoreceptor was prepared in exactly the same manner as in Example 1 except that the following comparative disazo pigment (1) described in JP-A-59-157644 was used. Then, the charging characteristics were investigated in the same manner as in Example 1. Furthermore, a similar evaluation was performed on a comparative pigment (2) having the following structure.
比較顔料(2) 結果を第2表に示す。Comparative pigment (2) The results are shown in Table 2.
第 2 表 は電位の低下を表わし、正記号は電位の上昇を表わす。Table 2 represents a decrease in potential, and a positive sign represents an increase in potential.
第
表
第1表および第2表より、本発明による電子写真感光体
は大きな感度を有するものであることがわかる。From Tables 1 and 2, it can be seen that the electrophotographic photoreceptor according to the present invention has high sensitivity.
実施例6〜10
実施例1〜5および比較例1.2で用いた感光体をコロ
ナ帯電器、露光光学系、現像器、転写帯電器、除電露光
光学系およびクリーナーを備えた電子写真機のシリンダ
ーに感光体を貼りつけた。この複写機はシリンダーの駆
動に伴い、転写紙上に画像が得られる構成になっている
。この複写機を用いて初期の明部電位(VL)と暗部電
位(VD)をそれぞれ−200V、−700Vに設定し
1万回使用した後の明部電位(VL100″)と暗部電
位(y 。+0000 )の変動量ΔvL1Δvoを測
定した。この結果を第3表に示す。尚ΔvD + Δv
Lにおける負記号第3表より、本発明のジスアゾ顔料を
用いた感光体は繰返し使用時の電位変動が少ないことが
わかる。Examples 6 to 10 The photoreceptors used in Examples 1 to 5 and Comparative Example 1.2 were used in an electrophotographic machine equipped with a corona charger, an exposure optical system, a developer, a transfer charger, a static elimination exposure optical system, and a cleaner. A photoreceptor was attached to the cylinder. This copying machine is configured to produce an image on transfer paper as a cylinder is driven. Using this copying machine, the initial bright area potential (VL) and dark area potential (VD) were set to -200V and -700V, respectively, and the bright area potential (VL100'') and dark area potential (y) after being used 10,000 times. +0000) was measured. The results are shown in Table 3. Note that ΔvD + Δv
From the negative sign in Table 3 for L, it can be seen that the photoreceptor using the disazo pigment of the present invention has less potential fluctuation during repeated use.
比較例5〜11
実施例1〜5、比較例1. 2で用いたスチリル化合物
(T−39)にかえて下記構造のヒドラゾン化合物を用
いる以外は実施例1〜5と全く同様にして感光体を作製
し帯電特性を測定した。また実施例6〜10と全く同様
にして電位変動量を測定した。結果を第4表に示す。Comparative Examples 5-11 Examples 1-5, Comparative Example 1. Photoreceptors were prepared in exactly the same manner as in Examples 1 to 5, except that a hydrazone compound having the following structure was used in place of the styryl compound (T-39) used in Example 2, and the charging characteristics were measured. Further, the amount of potential fluctuation was measured in exactly the same manner as in Examples 6 to 10. The results are shown in Table 4.
第4表
第4表より本発明のジスアゾ顔料とスチリル化合物とを
組合わせることで優れた特性を有する感光体を得ること
ができる。さらに本発明のジスアゾ顔料では、電荷輸送
物質が変わっても特性の劣化が小さく電荷輸送物質の選
択の幅が広いことがわかる。Table 4 From Table 4, a photoreceptor having excellent properties can be obtained by combining the disazo pigment of the present invention and a styryl compound. Furthermore, it can be seen that in the disazo pigment of the present invention, even if the charge transporting substance is changed, the characteristics deteriorate little and the range of selection of the charge transporting substance is wide.
実施例11
前記例示のジスアゾ顔料(G−45) 5gをシクロヘ
キサノン100mj!に混合しボールミルで10分間分
散した。この分散液を乾燥後の膜厚が0,5μmになる
ようにアルミ板上に塗布しキャリア発生層を形成した。Example 11 5 g of the above-exemplified disazo pigment (G-45) was mixed with 100 mj of cyclohexanone! and dispersed in a ball mill for 10 minutes. This dispersion was applied onto an aluminum plate to form a carrier generation layer so that the film thickness after drying was 0.5 μm.
次いで前記例示電荷輸送物質T−6010gとビスフェ
ノールA型ポリカーボネート樹脂(粘度平均分子量28
000) Logを1.2−ジクロロエタン70m1に
溶解し、この溶液を前記キャリア発生層の上に乾燥後の
膜厚が18μmとなるように塗布してキャリア輸送層を
形成させ本発明の電子写真感光体を作製した。Next, 10 g of the exemplary charge transport material T-60 and bisphenol A type polycarbonate resin (viscosity average molecular weight 28
000) Log is dissolved in 70 ml of 1,2-dichloroethane, and this solution is applied onto the carrier generation layer so that the film thickness after drying is 18 μm to form a carrier transport layer. The body was created.
以上のようにして得られた感光体を実施例1と同様にし
て電子写真特性を測定した。さらに同様の測定を100
0回繰り返して行った。さらに本実施例で用いた分散液
を1力月放置したのち、上記と同様の方法で感光体を作
製し電子写真特性を測定した。結果は第5表に示すとお
りである。The electrophotographic properties of the photoreceptor obtained as described above were measured in the same manner as in Example 1. 100 more similar measurements
This was repeated 0 times. Furthermore, after the dispersion used in this example was left to stand for one month, a photoreceptor was prepared in the same manner as above, and its electrophotographic properties were measured. The results are shown in Table 5.
第 5 表
第 6 表
比較例12
キャリア発生物質として特開昭59−7365号公報記
載の下記ビスアゾ顔料を用い実施例11と同様にして比
較感光体を作製した。Table 5 Table 6 Comparative Example 12 A comparative photoreceptor was prepared in the same manner as in Example 11 using the following bisazo pigment described in JP-A-59-7365 as a carrier generating material.
この比較感光体について実施例11と同様にして測定を
行ったところ第6表に示す結果を得た。When this comparative photoreceptor was measured in the same manner as in Example 11, the results shown in Table 6 were obtained.
以上の結果から明らかなように比較例のキャリア発生物
質は分散時間が短かくても特性を出すことはできるが分
散液の経時変化が大きく実用上大きな障害となる。本発
明の電子写真感光体は分散時間が短かくても十分な特性
を出すことができ、しかも分散液の経時変化がほとんど
無く実用上優れたものである。As is clear from the above results, the carrier-generating substance of the comparative example can exhibit characteristics even if the dispersion time is short, but the dispersion liquid changes over time and becomes a major obstacle in practical use. The electrophotographic photoreceptor of the present invention can exhibit sufficient characteristics even if the dispersion time is short, and there is almost no change in the dispersion liquid over time, making it excellent in practical use.
本発明によるジスアゾ顔料とスチリル化合物の組合せに
よれば感光層内部に於けるキャリア発生効率の向上、キ
ャリア輸送効率の向上がはかられ、結果的に高感度で耐
久性とりわけ電位安定性のすぐれた電子写真感光体を得
ることができる。また本発明のジスアゾ顔料はその分散
状態での安定性が良く実用上すぐれた特性を示す。さら
に本発明の感光体はアゾ顔料の置換基を選択することで
LEDの発光波長域で高感度な電子写真感度を示す。The combination of a disazo pigment and a styryl compound according to the present invention improves carrier generation efficiency and carrier transport efficiency within the photosensitive layer, resulting in high sensitivity, durability, and particularly excellent potential stability. An electrophotographic photoreceptor can be obtained. Further, the disazo pigment of the present invention has good stability in its dispersed state and exhibits excellent properties in practical use. Further, the photoreceptor of the present invention exhibits high electrophotographic sensitivity in the LED emission wavelength range by selecting substituents of the azo pigment.
第1図は電子写真感光体の層構成を示す模式図、第2図
および第3図は実施例の分光感度を示す図である。FIG. 1 is a schematic diagram showing the layer structure of an electrophotographic photoreceptor, and FIGS. 2 and 3 are diagrams showing the spectral sensitivity of Examples.
Claims (2)
る積層型電子写真感光体において、電荷発生層は電荷発
生物質として、 一般式(1) ▲数式、化学式、表等があります▼ (式中、R_1およびR_2はアルキル基、アラルキル
基、芳香環基、または複素環基を示し、Ar_1および
Ar_2は芳香環基または複素環基を示し、X_1、X
_2、X_3およびX_4は水素原子、アルキル基、ア
ルコキシ基、ハロゲン原子、ニトロ基、シアノ基または
トリフルオロメチル基を示し全てが水素原子であること
はない。Zは酸素原子又は硫黄原子を示す。) で示されるジスアゾ顔料を含有し、電荷輸送層は電荷輸
送物質として、 一般式(2) ▲数式、化学式、表等があります▼ あるいは 一般式(3) ▲数式、化学式、表等があります▼ (式中、R_3およびR_4はアルキル基、アラルキル
基、芳香環基または複素環基を示し、R_5およびR_
6は水素原子、アルキル基、アルコキシ基またはハロゲ
ン原子を示し、Ar_3は芳香環基または複素環基を示
す。Yは単結合、−CH_2−CH_2−または−CH
=CH−を示す。)で示されるスチリル化合物を含有す
ることを特徴とする電子写真感光体。(1) In a laminated electrophotographic photoreceptor that has a charge generation layer and a charge transport layer on a conductive support, the charge generation layer is a charge generation substance and has the general formula (1) ▲Mathematical formula, chemical formula, table, etc.▼ (In the formula, R_1 and R_2 represent an alkyl group, an aralkyl group, an aromatic ring group, or a heterocyclic group, Ar_1 and Ar_2 represent an aromatic ring group or a heterocyclic group, X_1,
_2, X_3 and X_4 represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, a cyano group or a trifluoromethyl group, and are not all hydrogen atoms. Z represents an oxygen atom or a sulfur atom. ) The charge transport layer contains a disazo pigment as a charge transport substance, and the general formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Or the general formula (3) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_3 and R_4 represent an alkyl group, an aralkyl group, an aromatic ring group or a heterocyclic group, and R_5 and R_
6 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, and Ar_3 represents an aromatic ring group or a heterocyclic group. Y is a single bond, -CH_2-CH_2- or -CH
=CH-. ) An electrophotographic photoreceptor comprising a styryl compound represented by:
アラルキル基、芳香環基、アルコキシ基、ハロゲン原子
、ニトロ基、シアノ基またはトリフルオロメチル基を示
し、R_9およびR_1_0は水素原子、アルキル基、
アラルキル基、芳香環基、アルコキシ基、ハロゲン原子
、シアノ基またはトリフルオロメチル基を示す。Z_1
、X_1、X_2、X_3およびX_4は一般式(1)
と同じ意味を示す。) で示されるジスアゾ顔料である特許請求の範囲第1項記
載の電子写真感光体。(2) The charge generating substance has the general formula (4) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_7 and R_8 are hydrogen atoms, alkyl groups,
It represents an aralkyl group, an aromatic ring group, an alkoxy group, a halogen atom, a nitro group, a cyano group, or a trifluoromethyl group, and R_9 and R_1_0 are a hydrogen atom, an alkyl group,
It represents an aralkyl group, an aromatic ring group, an alkoxy group, a halogen atom, a cyano group, or a trifluoromethyl group. Z_1
, X_1, X_2, X_3 and X_4 are general formula (1)
has the same meaning as ) The electrophotographic photoreceptor according to claim 1, which is a disazo pigment represented by:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26672088A JPH02113258A (en) | 1988-10-21 | 1988-10-21 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26672088A JPH02113258A (en) | 1988-10-21 | 1988-10-21 | Electrophotographic sensitive body |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH02113258A true JPH02113258A (en) | 1990-04-25 |
JPH0514271B2 JPH0514271B2 (en) | 1993-02-24 |
Family
ID=17434747
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP26672088A Granted JPH02113258A (en) | 1988-10-21 | 1988-10-21 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH02113258A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0575835A2 (en) * | 1992-06-17 | 1993-12-29 | Mitsubishi Paper Mills, Ltd. | Electrophotographic photoreceptor |
US7411072B2 (en) | 2002-06-26 | 2008-08-12 | Eli Lilly And Company | Tricyclic steroid hormone nuclear receptor modulators |
-
1988
- 1988-10-21 JP JP26672088A patent/JPH02113258A/en active Granted
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0575835A2 (en) * | 1992-06-17 | 1993-12-29 | Mitsubishi Paper Mills, Ltd. | Electrophotographic photoreceptor |
EP0575835A3 (en) * | 1992-06-17 | 1994-11-17 | Mitsubishi Paper Mills Ltd | Electrophotographic photoreceptor. |
US7411072B2 (en) | 2002-06-26 | 2008-08-12 | Eli Lilly And Company | Tricyclic steroid hormone nuclear receptor modulators |
Also Published As
Publication number | Publication date |
---|---|
JPH0514271B2 (en) | 1993-02-24 |
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