JPH0210947B2 - - Google Patents
Info
- Publication number
- JPH0210947B2 JPH0210947B2 JP20608981A JP20608981A JPH0210947B2 JP H0210947 B2 JPH0210947 B2 JP H0210947B2 JP 20608981 A JP20608981 A JP 20608981A JP 20608981 A JP20608981 A JP 20608981A JP H0210947 B2 JPH0210947 B2 JP H0210947B2
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- group
- phenyl
- unsubstituted
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 sulfoamide compound Chemical class 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 230000001235 sensitizing effect Effects 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 206010034972 Photosensitivity reaction Diseases 0.000 claims description 8
- 230000036211 photosensitivity Effects 0.000 claims description 8
- 229940124530 sulfonamide Drugs 0.000 claims description 8
- 239000000975 dye Substances 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 18
- 230000035945 sensitivity Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 7
- 206010070834 Sensitisation Diseases 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 230000008313 sensitization Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920002799 BoPET Polymers 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-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
- 229910006404 SnO 2 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- IPRJXAGUEGOFGG-UHFFFAOYSA-N N-butylbenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC=C1 IPRJXAGUEGOFGG-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- WTOSNONTQZJEBC-UHFFFAOYSA-N erythrosin Chemical compound OC(=O)C1=CC=CC=C1C(C1C(C(=C(O)C(I)=C1)I)O1)=C2C1=C(I)C(=O)C(I)=C2 WTOSNONTQZJEBC-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229940043267 rhodamine b Drugs 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000008096 xylene 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
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- AVKICCCNTFCREG-UHFFFAOYSA-N 1,1-dichlorohexan-2-one Chemical compound CCCCC(=O)C(Cl)Cl AVKICCCNTFCREG-UHFFFAOYSA-N 0.000 description 1
- 150000003920 1,2,4-triazines Chemical class 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OURODNXVJUWPMZ-UHFFFAOYSA-N 1,2-diphenylanthracene Chemical compound C1=CC=CC=C1C1=CC=C(C=C2C(C=CC=C2)=C2)C2=C1C1=CC=CC=C1 OURODNXVJUWPMZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KXJGSNRAQWDDJT-UHFFFAOYSA-N 1-acetyl-5-bromo-2h-indol-3-one Chemical compound BrC1=CC=C2N(C(=O)C)CC(=O)C2=C1 KXJGSNRAQWDDJT-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- HCFYTOYUYYYOPD-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetrabenzylbenzene-1,3-diamine Chemical compound C=1C=CC=CC=1CN(C=1C=C(C=CC=1)N(CC=1C=CC=CC=1)CC=1C=CC=CC=1)CC1=CC=CC=C1 HCFYTOYUYYYOPD-UHFFFAOYSA-N 0.000 description 1
- IOXVRZSNGAOKFG-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetraphenylbenzene-1,3-diamine Chemical compound C1=CC=CC=C1N(C=1C=C(C=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IOXVRZSNGAOKFG-UHFFFAOYSA-N 0.000 description 1
- VPTNBOIEKNYSFL-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetrabenzylbenzene-1,4-diamine Chemical compound C=1C=CC=CC=1CN(C=1C=CC(=CC=1)N(CC=1C=CC=CC=1)CC=1C=CC=CC=1)CC1=CC=CC=C1 VPTNBOIEKNYSFL-UHFFFAOYSA-N 0.000 description 1
- UUNVBJVJCPUYAG-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetrakis[(4-chlorophenyl)methyl]benzene-1,4-diamine Chemical compound C1=CC(Cl)=CC=C1CN(C=1C=CC(=CC=1)N(CC=1C=CC(Cl)=CC=1)CC=1C=CC(Cl)=CC=1)CC1=CC=C(Cl)C=C1 UUNVBJVJCPUYAG-UHFFFAOYSA-N 0.000 description 1
- CJAOGUFAAWZWNI-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetramethylbenzene-1,4-diamine Chemical compound CN(C)C1=CC=C(N(C)C)C=C1 CJAOGUFAAWZWNI-UHFFFAOYSA-N 0.000 description 1
- JPDUPGAVXNALOL-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetraphenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 JPDUPGAVXNALOL-UHFFFAOYSA-N 0.000 description 1
- BRSRUYVJULRMRQ-UHFFFAOYSA-N 1-phenylanthracene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 BRSRUYVJULRMRQ-UHFFFAOYSA-N 0.000 description 1
- FBNAYEYTRHHEOB-UHFFFAOYSA-N 2,3,5-triphenyl-1,3-dihydropyrazole Chemical compound N1N(C=2C=CC=CC=2)C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 FBNAYEYTRHHEOB-UHFFFAOYSA-N 0.000 description 1
- AXSVCKIFQVONHI-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-1-benzofuran-6-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)C2=CC=C(O)C=C2O1 AXSVCKIFQVONHI-UHFFFAOYSA-N 0.000 description 1
- BIECIOFZIILAAK-UHFFFAOYSA-N 2,3-diphenyl-5-(2-phenylethenyl)-1,3-dihydropyrazole Chemical compound N1N(C=2C=CC=CC=2)C(C=2C=CC=CC=2)C=C1C=CC1=CC=CC=C1 BIECIOFZIILAAK-UHFFFAOYSA-N 0.000 description 1
- GEZASDFBKHUKNE-UHFFFAOYSA-N 2,4-diphenylbenzo[h]quinazoline Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=CC=2C3=CC=CC=2)C3=N1 GEZASDFBKHUKNE-UHFFFAOYSA-N 0.000 description 1
- FPQJIXBKABHGGB-UHFFFAOYSA-N 2,5-diphenyl-3-(2-phenylethenyl)-1,3-dihydropyrazole Chemical compound C1=C(C=2C=CC=CC=2)NN(C=2C=CC=CC=2)C1C=CC1=CC=CC=C1 FPQJIXBKABHGGB-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 1
- OMXSHNIXAVHELO-UHFFFAOYSA-N 2-phenyl-4-(2-phenylethenyl)quinazoline Chemical compound C=1C=CC=CC=1C=CC(C1=CC=CC=C1N=1)=NC=1C1=CC=CC=C1 OMXSHNIXAVHELO-UHFFFAOYSA-N 0.000 description 1
- KKAJSJJFBSOMGS-UHFFFAOYSA-N 3,6-diamino-10-methylacridinium chloride Chemical compound [Cl-].C1=C(N)C=C2[N+](C)=C(C=C(N)C=C3)C3=CC2=C1 KKAJSJJFBSOMGS-UHFFFAOYSA-N 0.000 description 1
- MRXCTUHFMJGHPM-UHFFFAOYSA-N 3-(furan-2-yl)-2,5-diphenyl-1,3-dihydropyrazole Chemical compound N1N(C=2C=CC=CC=2)C(C=2OC=CC=2)C=C1C1=CC=CC=C1 MRXCTUHFMJGHPM-UHFFFAOYSA-N 0.000 description 1
- ZTXMSSUWNYFDCH-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-2-phenyl-1-benzofuran-6-ol Chemical compound C1=CC(N(C)C)=CC=C1C1=C(C=2C=CC=CC=2)OC2=CC(O)=CC=C12 ZTXMSSUWNYFDCH-UHFFFAOYSA-N 0.000 description 1
- CXROFFBCQOOZMD-UHFFFAOYSA-N 3-nitro-n-(3-nitrophenyl)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(NS(=O)(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 CXROFFBCQOOZMD-UHFFFAOYSA-N 0.000 description 1
- HXFZHDVPBWJOPB-UHFFFAOYSA-N 3h-1,3-benzothiazole-2-thione;copper Chemical compound [Cu].C1=CC=C2SC(=S)NC2=C1 HXFZHDVPBWJOPB-UHFFFAOYSA-N 0.000 description 1
- JHKQSICMMKJIAA-UHFFFAOYSA-N 3h-1,3-benzothiazole-2-thione;lead Chemical compound [Pb].C1=CC=C2SC(=S)NC2=C1 JHKQSICMMKJIAA-UHFFFAOYSA-N 0.000 description 1
- OFQGIIIVIXXLRO-UHFFFAOYSA-N 3h-1,3-benzoxazole-2-thione;lead Chemical compound [Pb].C1=CC=C2OC(=S)NC2=C1 OFQGIIIVIXXLRO-UHFFFAOYSA-N 0.000 description 1
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 1
- UECMVEOOXQNVNB-UHFFFAOYSA-N 4-(2,5-diphenyl-1,3-dihydropyrazol-3-yl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1N(C=2C=CC=CC=2)NC(C=2C=CC=CC=2)=C1 UECMVEOOXQNVNB-UHFFFAOYSA-N 0.000 description 1
- VHJNANHFHQRECS-UHFFFAOYSA-N 4-(4-methylphenyl)-2-phenylquinazoline Chemical compound C1=CC(C)=CC=C1C1=NC(C=2C=CC=CC=2)=NC2=CC=CC=C12 VHJNANHFHQRECS-UHFFFAOYSA-N 0.000 description 1
- JMMDGDGHMXNNFA-UHFFFAOYSA-N 4-(5,6-dipyridin-2-yl-1,2,4-triazin-3-yl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(N=C1C=2N=CC=CC=2)=NN=C1C1=CC=CC=N1 JMMDGDGHMXNNFA-UHFFFAOYSA-N 0.000 description 1
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 1
- NIGKTGXZVMXWCF-UHFFFAOYSA-N 4-[1-[4-(dimethylamino)phenyl]-1-phenylethyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C)(C=1C=CC(=CC=1)N(C)C)C1=CC=CC=C1 NIGKTGXZVMXWCF-UHFFFAOYSA-N 0.000 description 1
- QZDUCNZBMZXTCW-UHFFFAOYSA-N 4-[1-[4-[bis[(3-methylphenyl)methyl]amino]phenyl]propyl]-n,n-bis[(3-methylphenyl)methyl]aniline Chemical compound C=1C=C(N(CC=2C=C(C)C=CC=2)CC=2C=C(C)C=CC=2)C=CC=1C(CC)C(C=C1)=CC=C1N(CC=1C=C(C)C=CC=1)CC1=CC=CC(C)=C1 QZDUCNZBMZXTCW-UHFFFAOYSA-N 0.000 description 1
- NEZCBMZHMQVZOD-UHFFFAOYSA-N 4-[2-[3-[4-(dimethylamino)phenyl]-2-phenyl-1,3-dihydropyrazol-5-yl]ethenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)N(C)C)N(C=2C=CC=CC=2)N1 NEZCBMZHMQVZOD-UHFFFAOYSA-N 0.000 description 1
- CRDNXTRZWPMCAK-UHFFFAOYSA-N 4-[4-(diethylamino)phenoxy]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1OC1=CC=C(N(CC)CC)C=C1 CRDNXTRZWPMCAK-UHFFFAOYSA-N 0.000 description 1
- YRNWIFYIFSBPAU-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(N(C)C)C=C1 YRNWIFYIFSBPAU-UHFFFAOYSA-N 0.000 description 1
- JQOIQWPSIWKTNQ-UHFFFAOYSA-N 4-[5,6-bis(1,4-dimethoxycyclohexa-2,4-dien-1-yl)-1,2,4-triazin-3-yl]-n,n-dimethylaniline Chemical compound C1=CC(OC)=CCC1(OC)C1=NN=C(C=2C=CC(=CC=2)N(C)C)N=C1C1(OC)C=CC(OC)=CC1 JQOIQWPSIWKTNQ-UHFFFAOYSA-N 0.000 description 1
- VFUHOGIUERDLPZ-UHFFFAOYSA-N 4-[5,6-bis(4-ethoxyphenyl)-1,2,4-triazin-3-yl]-n,n-diethylaniline Chemical compound C1=CC(OCC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(CC)CC)N=C1C1=CC=C(OCC)C=C1 VFUHOGIUERDLPZ-UHFFFAOYSA-N 0.000 description 1
- XWUXTAPFYONTHE-UHFFFAOYSA-N 4-[5,6-bis(4-ethoxyphenyl)-1,2,4-triazin-3-yl]-n,n-dimethylaniline Chemical compound C1=CC(OCC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(C)C)N=C1C1=CC=C(OCC)C=C1 XWUXTAPFYONTHE-UHFFFAOYSA-N 0.000 description 1
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- FAPXNOXKLZJBMT-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazol-2-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(C)C)O1 FAPXNOXKLZJBMT-UHFFFAOYSA-N 0.000 description 1
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- KXHTVRFSFOPBFV-UHFFFAOYSA-N n,n-dibenzyl-4-[[4-(dibenzylamino)phenyl]methyl]aniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC=1)CC1=CC=CC=C1 KXHTVRFSFOPBFV-UHFFFAOYSA-N 0.000 description 1
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- VQVQWNNWJNMZFS-UHFFFAOYSA-N n,n-dimethyl-4-(2-phenylquinazolin-4-yl)aniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(C=2C=CC=CC=2)=NC2=CC=CC=C12 VQVQWNNWJNMZFS-UHFFFAOYSA-N 0.000 description 1
- UKXSFBOLCCYJRD-UHFFFAOYSA-N n-(3-methylbutyl)-4-[5-[4-(3-methylbutylamino)phenyl]-1,3,4-oxadiazol-2-yl]aniline Chemical compound C1=CC(NCCC(C)C)=CC=C1C1=NN=C(C=2C=CC(NCCC(C)C)=CC=2)O1 UKXSFBOLCCYJRD-UHFFFAOYSA-N 0.000 description 1
- YCVLNLXLOPCQCX-UHFFFAOYSA-N n-(4-chlorophenyl)ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=C(Cl)C=C1 YCVLNLXLOPCQCX-UHFFFAOYSA-N 0.000 description 1
- MFGPRXPCLKNJJM-UHFFFAOYSA-N n-(4-cyanophenyl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=CC=C(C#N)C=C1 MFGPRXPCLKNJJM-UHFFFAOYSA-N 0.000 description 1
- ZENKIQMTPMONLY-UHFFFAOYSA-N n-(4-nitrophenyl)ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1 ZENKIQMTPMONLY-UHFFFAOYSA-N 0.000 description 1
- BDMYVUTVARPUCD-UHFFFAOYSA-N n-benzyl-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C=1C=C2C=CC=CC2=CC=1N(C=1C=C2C=CC=CC2=CC=1)CC1=CC=CC=C1 BDMYVUTVARPUCD-UHFFFAOYSA-N 0.000 description 1
- FKJARBPQBIATJT-UHFFFAOYSA-N n-benzyl-n-phenylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)C1=CC=CC=C1 FKJARBPQBIATJT-UHFFFAOYSA-N 0.000 description 1
- VRUKENOGLFMZNY-UHFFFAOYSA-N n-cyclohexyl-n-phenylaniline Chemical compound C1CCCCC1N(C=1C=CC=CC=1)C1=CC=CC=C1 VRUKENOGLFMZNY-UHFFFAOYSA-N 0.000 description 1
- NYHDAJNHQXVAGT-UHFFFAOYSA-N n-cyclopentyl-4-[5-[4-(cyclopentylamino)phenyl]-1,3,4-oxadiazol-2-yl]aniline Chemical compound C1CCCC1NC1=CC=C(C=2OC(=NN=2)C=2C=CC(NC3CCCC3)=CC=2)C=C1 NYHDAJNHQXVAGT-UHFFFAOYSA-N 0.000 description 1
- IVFJZIZQJTWRCT-UHFFFAOYSA-N n-ethyl-4-[5-[4-(ethylamino)phenyl]-1,3,4-oxadiazol-2-yl]aniline Chemical compound C1=CC(NCC)=CC=C1C1=NN=C(C=2C=CC(NCC)=CC=2)O1 IVFJZIZQJTWRCT-UHFFFAOYSA-N 0.000 description 1
- WNSXUAGCWVZDQC-UHFFFAOYSA-N n-ethylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=CC=C1 WNSXUAGCWVZDQC-UHFFFAOYSA-N 0.000 description 1
- XAUGWFWQVYXATQ-UHFFFAOYSA-N n-phenylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=CC=CC=C1 XAUGWFWQVYXATQ-UHFFFAOYSA-N 0.000 description 1
- IQVSWLPEOQMCQD-UHFFFAOYSA-N n-phenylethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC=C1 IQVSWLPEOQMCQD-UHFFFAOYSA-N 0.000 description 1
- OKPTYPHVKNNPSG-UHFFFAOYSA-N n-propylbenzenesulfonamide Chemical compound CCCNS(=O)(=O)C1=CC=CC=C1 OKPTYPHVKNNPSG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical compound [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- PGNWIWKMXVDXHP-UHFFFAOYSA-L zinc;1,3-benzothiazole-2-thiolate Chemical compound [Zn+2].C1=CC=C2SC([S-])=NC2=C1.C1=CC=C2SC([S-])=NC2=C1 PGNWIWKMXVDXHP-UHFFFAOYSA-L 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
- G03G5/0698—Compounds of unspecified structure characterised by a substituent only
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
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The present invention relates to a photoconductive composition mainly composed of an organic photoconductor and an electrophotographic photosensitive material using the same in an electrophotographic photosensitive layer, and more specifically to a photoconductive composition mainly composed of an organic photoconductor and a sulfonamide compound. The present invention relates to a sensitive photoconductive composition and a highly sensitive electrophotographic material using the same in an electrophotographic photosensitive layer. Conventionally, many organic compounds have been known as photoconductors for photosensitive compositions for electrophotography, and it has been confirmed that some of these compounds have considerably high photosensitivity. However, at present, there are very few examples of actually using organic photoconductors as electrophotographic materials. Organic photoconductors have many superior properties compared to inorganic photoconductors and offer a wide range of applications in the field of electrophotography. For example, it is only possible to produce transparent electrophotographic films, flexible electrophotographic films, lightweight and easy-to-handle electrophotographic films, etc. using organic photoconductors. In addition, organic photoconductors have properties that cannot be expected from inorganic photoconductors, such as film-forming ability during the production of electrophotographic photosensitive materials, surface smoothness, and selectivity of charging polarity in the electrophotographic process. has. Although organic photoconductors have excellent properties in many respects, the main reasons why they have not been able to fully contribute to the field of electrophotography to date are mainly their low photosensitivity and coatings. This is due to the fragility of Research on organic photoconductors initially focused on compounds such as low molecular weight heterocyclic compounds, nitrogen-containing aromatic compounds, and various polymeric aromatic compounds. As a result, some compounds with considerably high sensitivity have been found, but recently there has been a tendency to focus on research on sensitization methods in order to achieve even higher sensitivity. This is because, even though it is the most highly sensitive organic photosemiconductor compound known to date, it does not have enough sensitivity to be put to practical use as it is without sensitization treatment. Therefore, in the actual use of organic photoconductors, it is essential to select the most effective sensitization method, and the industrial value of organic photoconductors depends on the applied sensitization method. It is no exaggeration to say that it depends on how highly sensitive an electrophotographic light-sensitive material can be ultimately provided. The most commonly known methods of sensitization are the addition of sensitizing dyes and the addition of Lewis acids, which are applicable to most organic photoconductors. The former is achieved by adding the spectral absorption properties of a dye to an organic photoconductor, and the latter is achieved by the appearance of new spectral sensitivity due to the formation of a donor-acceptor complex with the organic photoconductor. It brings about sensitization. The present inventors have been searching for a method to sensitize organic photoconductors, and have discovered that adding a sulfonamide compound to a photoconductive composition significantly increases photosensitivity, leading to the present invention. did. A first object of the present invention is to provide a highly sensitized photoconductive composition. A second object of the present invention is to provide an electrophotographic material having high sensitivity. The present invention relates to a photoconductive composition containing an organic photoconductor and a sulfonamide compound represented by the following general formula (). R 1 : A monovalent group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocycle. R 2 , R 3 : H, substituted or unsubstituted alkyl group,
A monovalent group consisting of a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle. The present invention also provides an electrophotographic photosensitive material comprising a photoconductive composition containing an organic photoconductor and a sulfonamide compound represented by the above general formula () on a support having at least an electrically conductive surface. The present invention relates to an electrophotographic material having layers. Although various organic photoconductors can be used in the present invention, organic photoconductors that can be dye-sensitized are preferred. The following can be mentioned as an example of an organic photoconductor. (i) Polymeric organic photoconductor: Polycyclic aromatic or heteroaromatic vinyl polymerized polymeric organic photoconductor containing Ï electrons. Naphthalene, anthracene, anthracene,
Cores of polycyclic aromatic hydrocarbons such as pyrene, perylene, acenaphthene, phenylanthracene, and diphenylanthracene; Cores of heteroaromatic compounds such as carbazole, indole, acridine, 2-phenylindole, and N-phenylcarbazole; and halogen- and lower alkyl-substituted derivatives thereof. In the present invention, vinyl polymer homopolymers and copolymers containing these nuclei are used as photoconductors. For example, vinyl polymers such as polyvinylnaphthalene, polyvinylanthracene, polyvinylpyrene, polyvinylperylene, polyacenaphthylene, polystyrylanthracene, polyvinylcarbazole, polyvinylindole, polyvinylacridine, polyanthrylmethylvinyl ether, polypyrenylmethylvinyl ether, polycarbazoly vinyl ether polymers such as ethyl vinyl ether and polyindolyl ethyl vinyl ether; epoxy resins such as polyglycidyl carbazole, polyglycidyl indole, and poly-p-glycidyl anthrylbenzene;
Polymers such as acrylic esters and methacrylic esters containing the above-mentioned nucleus having Ï electrons as a substituent, and copolymers thereof; and condensation polymers of the above-mentioned Ï-electron based compounds and formaldehyde. Among these, poly-N-vinylcarbazole has an aryl group, alkylaryl group, amino group, alkylamino group, dialkylamino group, arylamino group, diarylamino group, N-alkyl-N-arylamino group in the carbazole ring. ,
Poly-N-vinylcarbazole (hereinafter referred to as poly-N-vinylcarbazole) having substituents such as nitro groups and halogen atoms
It is called a vinyl-substituted carbazole. ) and N-vinylcarbazole copolymers are preferred. As the N-vinylcarbazole copolymer, N
-Ethylene carbazole constituent repeating unit
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ãã[Formula] [Q represents the same substituent as the substituent of the aforementioned poly-N-vinyl-substituted carbazole. ] A copolymer containing 50 mol% or more can be used. The remaining constituent repeating units of the N-vinylcarbazole copolymer include 1-phenylethylene, 1-cyanoethylene, 1-cyano-1-methylethylene, 1-chloroethylene, 1-(alkoxycarbonyl)ethylene, 1-Alkoxycarbonyl-1-methylethylene (styrene, acrylonitrile, methacrylonitrile, respectively)
Constituent repeating unit derived from vinyl chloride, alkyl acrylate, and alkyl methacrylate. As the alkyl group of the alkoxycarbonyl group, an alkyl having 1 to 18 carbon atoms can be used,
Specific examples thereof include methyl group, ethyl group, hexyl group, dodecyl group, octadecyl group, and 4-methylcyclohexyl group. ). Here, the constitutional repeating unit is referred to as "Kobunshi", Vol. 27, pp. 345-359 (1978).
(Pure and Applied Chemistry, Vol. 48, No.
373-385 (Japanese translation, 1976). (ii) Aromatic tertiary amino compounds: triphenylamine, N,N-dibenzylaniline, diphenylbenzylamine, N,N-di(p-chlorobenzyl)aniline, di(β-naphthyl)benzylamine, Tri(p-tolyl)amine, diphenylcyclohexylamine. (iii) Aromatic tertiary diamino compounds: N,N,N',N'-tetrabenzyl-p-phenylenediamine, N,N,N',N'-tetra(p
-chlorobenzyl)-p-phenylenediamine,
N,N,N',N'-tetramethyl-p-phenylenediamine, N,N,N',N'-tetrabenzyl-m-phenylenediamine, N,N,N',N'-
Tetramethylbenzidine, N,N,N',N'-tetrabenzylbenzidine, N,N,N',N'-tetraphenyl-p-phenylenediamine, N,
N,N',N'-tetraphenyl-m-phenylenediamine, 1,1-bis[4-(dibenzylamino)phenyl]ethane, 1,1-bis[4-(dibenzylamino)phenyl]propane, 1,1-
Bis[4-(dibenzylamino)phenyl]butane, 1,1-bis[4-(dibenzylamino)phenyl]-2-methylpropane, 2,2-bis[4-(dibenzylamino)phenyl]propane ,
2,2-bis[4-(dibenzylamino)phenyl]butane, 1,1-bis[4-[di(m-methylbenzyl)amino]phenyl]propane, bis[p-(dimethylamino)phenyl]phenylmethane , bis[p-(diethylamino)phenyl]
Phenylmethane, bis[4-(dibenzylamino)phenyl]methane, bis[4-[di(p-chlorobenzyl)amino]phenyl]methane, 1,
1-bis[p-(dimethylamino)phenyl]-
1-phenylethane, 4,4â²-benzylidenebis(N,N-dimethyl-m-toluidine), 4â²,4â³-
Bis(diethylamino)-2,6-dichloro-
2â²,2â³-dimethyltriphenylmethane, bis[4
-(diethylamino)-2-methylphenyl]α
-Naphthylmethane, 4',4''-bis(dimethylamino)-2-chloro-2',2''-dimethyltriphenylmethane, 1,1-bis[p-(diethylamino)phenyl]-1-phenylethane, 1 ,1-
Diphenyl-5,5-bis[4-(diethylamino)-2-methylphenyl]-1,3-pentadiene, 1,1-diphenyl-3,3-bis[4-
(diethylamino)-2-methylphenyl]-1
-Propene, bis[4-dibenzylamino)phenyl]ether, bis[4-(diethylamino)
phenyl]ether, bis[4-(dibenzylamino)phenyl]sulfide, 2,2-bis[4
-(di-p-tolylamino)phenyl]propane, 1,1-bis[4-(di-p-tolylamino)phenyl]-1-phenylethane, bis[4
-(dibenzylamino)phenyl]diphenylmethane. (iv) Aromatic tertiary triamino compound: tris[4-(diethylamino)phenyl]methane, 1,1-bis[4-diethylamino)-2
-Methylphenyl]-1-[4-(dimethylamino)phenyl]methane. (v) Condensation products: condensation products of aldehydes and aromatic amines, condensation products of tertiary aromatic amines and aromatic halides, poly-p-phenylene-1,3,4-oxadiazole , a condensation product of formaldehyde and a condensed polycyclic aromatic compound. (vi) Metal-containing compounds: 2-mercaptobenzothiazole lead salt, 2-mercaptobenzothiazole zinc salt, 2-mercaptobenzothiazole copper salt, 2-mercaptobenzoxazole lead salt, 2-mercapto-5-phenylbenzoxazole lead salt, 2-mercapto-6
-Methoxybenzimidazole lead salt, 8-hydroxyquinoline magnesium salt, 8-hydroxyquinoline aluminum salt, 8-hydroxyquinoline lead salt, 7-benzyl-8-hydroxyquinoline copper salt, 2-hydroxy-4-methylazobenzene copper salt, 2-Hydroxybenzoldemine zinc salt (vii) Heterocyclic compounds: (a) Pyrazoline derivatives: 1,3,5-triphenylpyrazoline, 1-
Phenyl-3-[p-(dimethylamino)styryl]-5-[p-(dimethylamino)phenyl]pyrazoline, 1,5-diphenyl-3-styrylpyrazoline, 1,3-diphenyl-5-
Styrylpyrazoline, 1,3-diphenyl-5
-[p-(dimethylamino)phenyl]pyrazoline, 1,3-diphenyl-5-(2-furyl)pyrazoline. (b) 1,2,4-triazine derivative: 3-[p-(dimethylamino)phenyl]-
5,6-di(p-dimethoxyphenyl)-1,
2,4-triazine, 3-[p-(dimethylamino)phenyl]-5,6-di(2-pyridyl)-1,2,4-triazine, 3-[p-
(dimethylamino)phenyl]-5,6-di(p-ethoxyphenyl)-1,2,4-triazine, 3-[p-(diethylamino)phenyl]-5,6-bis(p-methoxyphenyl) )
-1,2,4-triazine, 3-[p-(diethylamino)phenyl]-5,6-bis(p-
ethoxyphenyl)-1,2,4-triazine. (c) Quinazoline derivatives: 2,4-diphenylquinazolyl, 2-phenyl-4-p-tolylquinazoline, 2-phenyl-4-[4-(dimethylamino)phenyl]quinazoline, 2-phenyl-4- Styrylquinazoline, 2,4-diphenylbenzo[h]quinazoline. (d) Benzofuran derivative: 6-hydroxy-2-phenyl-3-[4-
(dimethylamino)phenyl]benzofuran,
6-hydroxy-2,3-di(4-methoxyphenyl)benzofuran, 2,3,5,6-tetra(4-methoxyphenyl)benzo[1,2-
b: 5,4-b'] difuran. (e) Oxadiazole derivative: 2,5-bis[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, 2,
5-bis[4-(diethylamino)phenyl]
-1,3,4-oxadiazole, 2,5-bis[4-(isoamylamino)phenyl]-
1,3,4-oxadiazole, 2,5-bis[4-(cyclopentylamino)phenyl]-
1,3,4-oxadiazole, 2,5-bis[4-(ethylamino)phenyl]-1,3,
4-Oxadiazole. The sulfonamide compound used in the present invention is represented by the following general formula (). [R 1 : Monovalent group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocycle. R 2 , R 3 : H, substituted or unsubstituted alkyl group,
A monovalent group consisting of a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle. ] In the above general formula, the alkyl group usually has 1 carbon number.
~15, and may be either saturated or unsaturated, linear or branched. In addition, the aryl group is usually a phenyl group, a naphthyl group, or a heterocyclic ring.
The valent groups are furanyl, pyridyl, oxazolyl, thiazolyl, and imidazolyl. Any of the sulfonamide compounds represented by the general formula () used in the present invention can be synthesized by reacting sulfonyl chloride with an amine. Among the sulfonamide compounds used in the present invention, compounds with particularly remarkable effects have the general formula () ~
It is shown in parentheses. In the formula,
~11), halogen, nitro group, cyano group, n, m
is an integer of 0 to 3 representing the number of substituents, R 4 and R 5 are substituted or unsubstituted alkyl groups, substituted or unsubstituted pyridyl groups. Further, examples of the above-mentioned substituents include halogen, hydroxyl group, and nitro group. The above alkyl group may be saturated or unsaturated, linear or branched. X and Y are o-, m of phenyl group
--, p-- may be placed in either position. It has been found that the compound represented by the general formula () not only works as a sensitizer, but also works as an agent for improving the film strength when polyvinylcarbazole is used as an organic photoconductor. Specific examples of the compound represented by the general formula () include benzenesulfonanilide, 4-chlorobenzenesulfonanilide, 4,4'-dichlorobenzenesulfonanilide, 4-nitrobenzenesulfonanilide, 4-methyl-4'-nitrobenzenesulfonanilide. , 4'-cyanobenzenesulfonanilide, 3,3'-dinitrobenzenesulfonanilide, and the like. Specific examples of the compound represented by the general formula () include N-ethylbenzenesulfonamide, N-butylbenzenesulfonamide, and N-propylbenzenesulfonamide. Specific examples of the compound represented by the general formula () include ethanesulfonanilide, 4'-chloroethanesulfonanilide, 4'-nitroethanesulfonanilide, and 4'-nitrobutanesulfonanilide. In the present invention, the content ratio of the compound represented by the general formula () in the photoconductive composition is determined in relation to the amount of the organic photoconductor that contributes to photoconductivity, and is determined based on the amount of the organic photoconductor that contributes to photoconductivity. The quantitative ratio of the compound represented by the general formula () is from 1 part by weight.
100 parts by weight, preferably in the range from 3 parts to 30 parts by weight. If the content exceeds the above ratio, the photosensitivity of the photoconductive composition tends to decrease or the residual potential increases. In the present invention, a sensitizing dye capable of increasing the photosensitivity of the organic photoconductor is added to a photoconductive composition containing an organic photoconductor and a compound represented by the general formula (). Thus, the sensitivity of the photoconductive composition can be further increased. The sensitizing dye used in the present invention is a well-known sensitizing dye used in the technique of dye sensitization of organic photoconductors. These sensitizing dyes are
Photographic Scientists and Engineersâ 19 ,
60-64 (1975), âApplied Opticsâ Suppl. 3 , 50
(1969), United States Patent (hereinafter abbreviated as USP)
3037861, USP3250615, USP3712811, British patent
1353264, âResearch Disclosureâ #10938 ( 109 ,
May 1973 issue, p. 62 onwards), USP3141700,
USP3938994, 14560, 14560, 14560
14561, JP 1984-29586, JP 56-29587, JP 56-65885, JP 1984-114259, JP 1982-
Various sensitizing dyes disclosed in Japanese Patent No. 35141 and others are representative, and these known sensitizing dyes and other dyes that can increase the photosensitivity of the polymeric organic photoconductor may be selected as appropriate. It can be used as Specific examples of the above-mentioned sensitizing dyes include the following. Triphenylmethane dyes such as Brilliant Green, Victoria Brieux B, Methyl Violet, Crystal Violet, Acid Violet 6B; Rhodamine B, Rhodamine 6G, Rhodamine G Extra, Sulfurhodamine B, Fast Acid Eosin G Rhodamines such as eosin S, eosin A, erythrosin, phloxine, rose bengal, fluorescein;
Thiazine dyes such as blue; acridine dyes such as acridine yellow, acridine orange, and trypaflavin; quinoline dyes such as pinacyanol, cryptocyanine; quinone and ketone dyes such as alizarin, alizarin red S, and quinizarin; cyanine Dye; chlorophyll; violet fuchsin, erythrosin
Allylmethane dyes such as 2Na, Rhodamine B500, Fuanal Pink B, Rhodamine 6GDN, Auramine; Polymethine dyes such as 3,3'-diethyl thiacarbocyanine iodide; Azo dyes such as Eriochrome Blue Black R; Bis( p
-Azomethine dyes such as dimethylaminobenzal) azine; Carbonyl dyes such as Solway Ultra Blue B and Alizarin Cyanine Green GWA; Heterocyclic compounds such as N,N-pentamethylenebis(benzthiazole) perchlorate; Segnar, Night Phthalocyanine dyes such as , Turquoise NB; 2,6-di-t-butyl-4-
(2,6-di-t-butyl-4H-thiopyran-4
-Indenemethyl)thiapyrylium salt, 2,6-
Di-t-butyl-4-[3-2,6-di-t-butyl-4H-thiapyran-4-indene)propen-1-yl)thiapyrylium salt, 2,6-diphenyl-4-(4-diethylamino phenyl) thiapyrylium salt, 2,6-di-t-butyl-4-
Pyrylium dyes such as (4-diethylaminostyryl) thiapyrylium salt. These sensitizing dyes are used in an amount that will sensitize the organic photoconductor as a component, and the amount varies depending on the type of organic photoconductor and sensitizing dye, but in general, 100% of the organic photoconductor is used. The weight ratio ranges from about 0.01 parts to about 100 parts by weight, preferably from about 0.1 parts to about 30 parts by weight. In addition, known structure agents, plasticizers, dyes, pigments, etc. may be added to the photoconductive composition of the present invention, as necessary. It can be contained within a certain range. Cyanoethylcellulose, nitrile rubber, bisphenol A polycarbonate as reinforcing agents,
Linear polyester styrene-butadiene copolymer, vinylidene chloride-acrylonitrile copolymer, etc. can be used. As the plasticizer, chlorinated biphenyl, epoxy resin, triphenylmethane compound, coumaron resin, low molecular weight xylene resin, etc. can be used. To prepare the photoconductive composition of the present invention, in addition to the above-mentioned two components, optionally added components are dispersed or dissolved in a dispersion medium or solvent in a desired ratio to form a dispersion or a uniform solution. prepared, then coated on a suitable support, and the dispersion medium or solvent removed (e.g.
It can be prepared by evaporation). Depending on the purpose, the photoconductive composition may be used as a dispersion or solution without completely removing the solvent. The electrophotographic photosensitive layer of the present invention is generally used by coating the photoconductive composition solution thus obtained on a support having a suitable conductive surface and drying it to form a photoconductive layer. Depending on the application, lamination with adhesive or the like is also possible. As the solvent or dispersion medium used for preparing the coating solution, benzene, toluene, xylene, chlorobenzene, dichloromethane, dichloroethane, trichloroethane, dichlorohexanone, tetrahydrofuran, dioxane, etc., and mixtures thereof, organic photoconductors, sensitized A medium can be used that dissolves or disperses the dye, the compound represented by the general formula (), and optionally added components. Supports with conductive surfaces include drums and sheets of metals such as aluminum, copper, iron, and zinc, vapor-deposited films of metals such as aluminum, copper, zinc, and indium, and conductive metal compounds (e.g., In 2 O 3 ,
Vapor-deposited film of SnO 2 ), metal foil laminate or carbon black, conductive metal compound (e.g. In 2 O 3 ,
Paper, plastic, glass, etc. whose surfaces have been treated to conductivity by dispersing SnO 2 ) powder or metal powder in a binder polymer and applying the coating are used. According to the present invention, by incorporating a compound represented by the general formula () into a photoconductive composition containing an organic photoconductor, a high degree of transparency can be achieved without impairing transparency, lightness, and mechanical strength. A sensitized electrophotographic film can be obtained. The photoconductive composition of the present invention can be prepared by finely dispersing the photoconductive composition in an insulating solvent, and
No. 3384565 (Special Publication No. 43-21781), U.S. Patent No.
No. 3384488 (Special Publication No. 47-37125), U.S. Patent No.
Images can also be formed by the electrophoretic imaging method described in specifications such as No. 3510419 (Japanese Patent Publication No. 46-36079). The present invention will be specifically illustrated in detail below based on Examples. Example 1 1 g of poly-N-vinylcarbazole (PVCz)
A solution was prepared by dissolving 1,2-dichloroethane in 20 ml, and 25 mg of 2,6-di-t-butyl-4 was added to this solution.
-[4-(N-methyl-N-2-cyanoethylamino)styryl]thiapyrylium tetrafluoroborate was added. A 100 ÎŒm thick polyethylene terephthalate (PET) film (In 2 O 3 conductive PET film) with a 60 nm thick In 2 O 3 vapor-deposited layer was coated with the above solution, and the solvent was removed by drying.
A 5 ÎŒm photoconductive layer (electrophotographic photosensitive layer) was formed to produce electrophotographic film No. 1. Prepare the same PVCz solution as above, add the indicated amount of the amide compound listed in Table 1 to 100 parts by weight of PVCz, and add this solution as above.
Electrophotographic films No. 2 to No. 17 were prepared by coating an In 2 O 3 conductive PET film, drying it, removing the solvent, and providing a photoconductive layer with a thickness of 5 ÎŒm. The sensitivity of the photoconductive layer of the electrophotographic films No. 1 to No. 17 was measured. Sensitivity measurement is at initial potential (500V)
The exposure amount (E 50 ) is reduced by 1/2 due to optical attenuation, and 1/1
The results are shown in Table 1 . The light source used was 630 nm monochromatic light. Example 2 2,6-di-t-butyl-4-[4
-(N-Methyl-N-cyanoethylaminostyryl)thiapyrylium tetrafluoroborate 25mg
2,6-di-t-butyl-4-[4
-(N,N-dichloroethyl)aminostyryl]
Electrophotographic films No. 18 and No. 3 were prepared in the same manner as in Example 1, No. 1, No. 2, and No. 3, except that 25 mg of thiapyrylium tetrafluoroborate and 25 mg of rhodamine B (CI#45170) were used. 19, No.20, No.21, No.22, No.
23, No.24, No.25, No.26, No.29, No.22, No.29, No.
30, No. 31 was obtained, and the sensitivity was measured in the same manner as in Example 1. The results are shown in Table 2. Example 3 Instead of the In 2 O 3 conductive PET film of Example 1, a SnO 2 fine powder/gelatin layer prepared by the method described in Examples 1 and 2 of Japanese Patent Application No. 55-47665 was used.
No. 1 of Example 1, except that PET film was used.
Electrophotographic film No. 2 and No. 3 were prepared in the same manner as No. 2 and No. 3.
32, No. 33, and No. 34 were obtained. Sensitivity was measured according to the method described in Example 1. The results are shown in Table 2.
ãè¡šããtableã
ãè¡šããtableã
Claims (1)
瀺ãããã¹ã«ããªã¢ããååç©ãå«æããããšã
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å æ床ãå¢å€§ããããå¢æè²çŽ ãå«æãããã®ã§
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åçæå ææã R1ïŒçœ®æåã¯ç¡çœ®æã®ã¢ã«ãã«åºã眮æåã¯
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ãç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®é»ååçæå æ
æã[Scope of Claims] 1. A photoconductive composition comprising an organic photoconductor and a sulfoamide compound represented by the following general formula (). R 1 : A monovalent group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocycle. R 2 , R 3 : H, substituted or unsubstituted alkyl group,
A monovalent group consisting of a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle. 2. The photoconductive composition according to claim 1, wherein the photoconductive composition further contains a sensitizing dye capable of increasing the photosensitivity of the organic photoconductor. 3 An electrophotographic photosensitive layer comprising an electrophotographic photosensitive layer comprising a photoconductive composition containing an organic photoconductor and a sulfonamide compound represented by the following general formula () on a support having at least an electrically conductive surface. material. R 1 : A monovalent group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocycle. R 2 , R 3 : H, substituted or unsubstituted alkyl group,
A monovalent group consisting of a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle. 4. The electrophotographic light-sensitive material according to claim 3, wherein the photoconductive composition further contains a sensitizing dye capable of increasing the photosensitivity of the organic photoconductor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20608981A JPS58107544A (en) | 1981-12-22 | 1981-12-22 | Photoconductive composition and electrophotographic sensitive material using it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20608981A JPS58107544A (en) | 1981-12-22 | 1981-12-22 | Photoconductive composition and electrophotographic sensitive material using it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58107544A JPS58107544A (en) | 1983-06-27 |
| JPH0210947B2 true JPH0210947B2 (en) | 1990-03-12 |
Family
ID=16517627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20608981A Granted JPS58107544A (en) | 1981-12-22 | 1981-12-22 | Photoconductive composition and electrophotographic sensitive material using it |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58107544A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8318394B2 (en) * | 2009-12-22 | 2012-11-27 | Xerox Corporation | Sulfonamide containing photoconductors |
-
1981
- 1981-12-22 JP JP20608981A patent/JPS58107544A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58107544A (en) | 1983-06-27 |
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