JPH0210945B2 - - Google Patents
Info
- Publication number
- JPH0210945B2 JPH0210945B2 JP56165260A JP16526081A JPH0210945B2 JP H0210945 B2 JPH0210945 B2 JP H0210945B2 JP 56165260 A JP56165260 A JP 56165260A JP 16526081 A JP16526081 A JP 16526081A JP H0210945 B2 JPH0210945 B2 JP H0210945B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- phenyl
- bis
- electrophotographic
- 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.)
- Expired
Links
- -1 urea compound Chemical class 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 230000001235 sensitizing effect Effects 0.000 claims description 16
- 206010034972 Photosensitivity reaction Diseases 0.000 claims description 13
- 230000036211 photosensitivity Effects 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000004202 carbamide Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000010410 layer Substances 0.000 description 21
- 239000000975 dye Substances 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 7
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 7
- 206010070834 Sensitisation Diseases 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000008313 sensitization Effects 0.000 description 6
- 150000003672 ureas Chemical class 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 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
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- RECCURWJDVZHIH-UHFFFAOYSA-N (4-chlorophenyl)urea Chemical compound NC(=O)NC1=CC=C(Cl)C=C1 RECCURWJDVZHIH-UHFFFAOYSA-N 0.000 description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- 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
- 229910006404 SnO 2 Inorganic materials 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 150000002391 heterocyclic compounds 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
- 230000014759 maintenance of location Effects 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 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
- 239000000843 powder Substances 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 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
- 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
- 125000004815 1,2-dimethylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([*:2])C([H])([H])[H] 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
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- JLFJUBXZKUXFTP-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[2-[(4-bromophenyl)carbamoylamino]ethyl]urea Chemical compound C1=CC(Br)=CC=C1NC(=O)NCCNC(=O)NC1=CC=C(Br)C=C1 JLFJUBXZKUXFTP-UHFFFAOYSA-N 0.000 description 1
- WLEKAZKMFWSJIK-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-[(4-chlorophenyl)carbamoylamino]phenyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC(C=C1)=CC=C1NC(=O)NC1=CC=C(Br)C=C1 WLEKAZKMFWSJIK-UHFFFAOYSA-N 0.000 description 1
- GUNDEIBZUWFUQA-UHFFFAOYSA-N 1-(4-bromophenyl)-3-ethylurea Chemical compound CCNC(=O)NC1=CC=C(Br)C=C1 GUNDEIBZUWFUQA-UHFFFAOYSA-N 0.000 description 1
- UVTMXZWZBDRRMD-UHFFFAOYSA-N 1-(4-bromophenyl)-3-naphthalen-1-ylurea Chemical compound C1=CC(Br)=CC=C1NC(=O)NC1=CC=CC2=CC=CC=C12 UVTMXZWZBDRRMD-UHFFFAOYSA-N 0.000 description 1
- YMLFJCGIYSWYJU-UHFFFAOYSA-N 1-(4-chloro-2-methylphenyl)-3-naphthalen-1-ylurea Chemical compound CC1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC2=CC=CC=C12 YMLFJCGIYSWYJU-UHFFFAOYSA-N 0.000 description 1
- KLDDYMGIGKKUFB-UHFFFAOYSA-N 1-(4-chlorophenyl)-1,3-diethylurea Chemical compound CCNC(=O)N(CC)C1=CC=C(Cl)C=C1 KLDDYMGIGKKUFB-UHFFFAOYSA-N 0.000 description 1
- XLUJTXUIQHBVGV-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[2-[(4-chlorophenyl)carbamoylamino]ethyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCCNC(=O)NC1=CC=C(Cl)C=C1 XLUJTXUIQHBVGV-UHFFFAOYSA-N 0.000 description 1
- RQQKDTUHWQBXQK-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-(phenylcarbamoylamino)phenyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 RQQKDTUHWQBXQK-UHFFFAOYSA-N 0.000 description 1
- DJSDFROQFMULFQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-[(4-chlorophenyl)carbamoylamino]phenyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC(C=C1)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 DJSDFROQFMULFQ-UHFFFAOYSA-N 0.000 description 1
- SHWMALCAIDXDLC-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[6-[(4-chlorophenyl)carbamoylamino]hexyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCCCCCCNC(=O)NC1=CC=C(Cl)C=C1 SHWMALCAIDXDLC-UHFFFAOYSA-N 0.000 description 1
- BUQNPNBBHVNTJO-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-ethylurea Chemical compound CCNC(=O)NC1=CC=C(Cl)C=C1 BUQNPNBBHVNTJO-UHFFFAOYSA-N 0.000 description 1
- OUYIIIGCEKDAEQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-naphthalen-1-ylurea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC2=CC=CC=C12 OUYIIIGCEKDAEQ-UHFFFAOYSA-N 0.000 description 1
- YUGWOJFOEIUCNJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-naphthalen-2-ylurea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(C=CC=C2)C2=C1 YUGWOJFOEIUCNJ-UHFFFAOYSA-N 0.000 description 1
- OXSPWPMUIDSJAA-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[4-[(4-methylphenyl)carbamoylamino]phenyl]urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C=C1)=CC=C1NC(=O)NC1=CC=C(C#N)C=C1 OXSPWPMUIDSJAA-UHFFFAOYSA-N 0.000 description 1
- SYIWRGKXYDMVNO-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[6-[(4-cyanophenyl)carbamoylamino]hexyl]urea Chemical compound C=1C=C(C#N)C=CC=1NC(=O)NCCCCCCNC(=O)NC1=CC=C(C#N)C=C1 SYIWRGKXYDMVNO-UHFFFAOYSA-N 0.000 description 1
- NQGCXTGGKQINBX-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-ethylurea Chemical compound CCNC(=O)NC1=CC=C(C#N)C=C1 NQGCXTGGKQINBX-UHFFFAOYSA-N 0.000 description 1
- KUHTZMQGCCPEST-UHFFFAOYSA-N 1-(4-ethylphenyl)-3-[4-[(4-nitrophenyl)carbamoylamino]phenyl]urea Chemical compound C1=CC(CC)=CC=C1NC(=O)NC(C=C1)=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 KUHTZMQGCCPEST-UHFFFAOYSA-N 0.000 description 1
- IPWHVEFFZGMDFD-UHFFFAOYSA-N 1-(4-methylphenyl)-3-naphthalen-1-ylurea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=CC2=CC=CC=C12 IPWHVEFFZGMDFD-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
- DOUCJWNVCGEZRR-UHFFFAOYSA-N 1-butyl-3-phenylurea Chemical compound CCCCNC(=O)NC1=CC=CC=C1 DOUCJWNVCGEZRR-UHFFFAOYSA-N 0.000 description 1
- XUFXDODGXLVPNJ-UHFFFAOYSA-N 1-ethyl-3-phenylurea Chemical compound CCNC(=O)NC1=CC=CC=C1 XUFXDODGXLVPNJ-UHFFFAOYSA-N 0.000 description 1
- 125000004812 1-ethylethylene group Chemical group [H]C([H])([H])C([H])([H])C([H])([*:1])C([H])([H])[*:2] 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
- HXIKAEAULDUNBD-UHFFFAOYSA-N 1-naphthalen-1-yl-3-phenylurea Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=O)NC1=CC=CC=C1 HXIKAEAULDUNBD-UHFFFAOYSA-N 0.000 description 1
- MLWGGCOCOBXOFA-UHFFFAOYSA-N 1-naphthalen-2-yl-3-phenylurea Chemical compound C=1C=C2C=CC=CC2=CC=1NC(=O)NC1=CC=CC=C1 MLWGGCOCOBXOFA-UHFFFAOYSA-N 0.000 description 1
- DQOGBYHDAMONNQ-UHFFFAOYSA-N 1-octyl-3-phenylurea Chemical compound CCCCCCCCNC(=O)NC1=CC=CC=C1 DQOGBYHDAMONNQ-UHFFFAOYSA-N 0.000 description 1
- CDTIOGUIESQOJT-UHFFFAOYSA-N 1-phenyl-3-[2-(phenylcarbamoylamino)ethyl]urea Chemical compound C=1C=CC=CC=1NC(=O)NCCNC(=O)NC1=CC=CC=C1 CDTIOGUIESQOJT-UHFFFAOYSA-N 0.000 description 1
- JTBDQDFUQGNSBW-UHFFFAOYSA-N 1-phenyl-3-[4-(phenylcarbamoylamino)phenyl]urea Chemical compound C=1C=C(NC(=O)NC=2C=CC=CC=2)C=CC=1NC(=O)NC1=CC=CC=C1 JTBDQDFUQGNSBW-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
- QAHMKHHCOXNIHO-UHFFFAOYSA-N 2,4-diphenylquinazoline Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 QAHMKHHCOXNIHO-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
- 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
- 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
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- 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
- 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- UBBIDOUCHSVOFY-UHFFFAOYSA-N octylurea Chemical compound CCCCCCCCNC(N)=O UBBIDOUCHSVOFY-UHFFFAOYSA-N 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
- 239000000123 paper Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 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
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 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
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000004065 semiconductor Substances 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
- 238000006467 substitution reaction Methods 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- G03G5/0622—Heterocyclic compounds
- G03G5/0644—Heterocyclic compounds containing two or more hetero rings
- G03G5/0661—Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring
-
- 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
- G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
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Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ ææ©å å°é»äœããã³äžèšäžè¬åŒïŒïŒãŸ
ãã¯ïŒïŒã§è¡šããããå°¿çŽ ååç©ãå«æããã
ãšãç¹åŸŽãšããå å°é»æ§çµæç©ã äžè¬åŒïŒïŒããã³ïŒïŒã«ãããŠãR1ä¹è³
R6ã¯ããããæ°ŽçŽ ååïŒã¢ã«ãã«åºïŒåç°åŒãŸ
ãã¯ïŒç°çž®ååŒã®ã¢ãªãŒã«åºãŸãã¯è€çŽ ç°ããèª
å°ãããïŒäŸ¡åºãè¡šãããäºãã«åãã§ãç°ãªã€
ãŠããããR1ãšR2ããŸãã¯R3ãšR4ã¯ããããã
é£çµããŠããŠããããäžè¬åŒïŒïŒã«ãããŠã¯
R1ä¹è³R4ãé£çµããŠå šäœãšããŠæ¶æ©ç°ã圢æã
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èŒã®å å°é»æ§çµæç©ã ïŒ å°ãªããšãè¡šé¢ãé»æ°äŒå°æ§ãæããæ¯æäœ
ã®äžã«ææ©å å°é»äœããã³äžèšäžè¬åŒïŒïŒ
ãŸãã¯ïŒïŒã§è¡šããããå°¿çŽ ååç©ãå«æãã
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ãã¯ïŒç°çž®ååŒã®ã¢ãªãŒã«åºãŸãã¯è€çŽ ç°ããèª
å°ãããïŒäŸ¡åºãè¡šãããäºãã«åãã§ãç°ãªã€
ãŠããããR1ãšR2ããŸãã¯R3ãšR4ã¯ããããã
é£çµããŠããŠããããäžè¬åŒïŒïŒã«ãããŠã¯
R1ä¹è³R4ãé£çµããŠå šäœãšããŠæ¶æ©ç°ã圢æã
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ã¬ã³åºãŸãã¯ã¢ã«ãã¬ã³åºãè¡šããã ïŒ åèšå å°é»æ§çµæç©ã®å±€ãããã«åèšææ©
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æã
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56165260A JPS5865438A (ja) | 1981-10-15 | 1981-10-15 | å å°é»æ§çµæç©ããã³ãããçšããé»ååçæå ææ |
| DE19823238126 DE3238126A1 (de) | 1981-10-15 | 1982-10-14 | Photoleitfaehige masse und diese enthaltendes elektrophotographisches lichtempfindliches material |
| US06/434,695 US4444863A (en) | 1981-10-15 | 1982-10-15 | Photoconductive composition and electrophotographic light-sensitive material using said composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56165260A JPS5865438A (ja) | 1981-10-15 | 1981-10-15 | å å°é»æ§çµæç©ããã³ãããçšããé»ååçæå ææ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5865438A JPS5865438A (ja) | 1983-04-19 |
| JPH0210945B2 true JPH0210945B2 (ja) | 1990-03-12 |
Family
ID=15808939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56165260A Granted JPS5865438A (ja) | 1981-10-15 | 1981-10-15 | å å°é»æ§çµæç©ããã³ãããçšããé»ååçæå ææ |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4444863A (ja) |
| JP (1) | JPS5865438A (ja) |
| DE (1) | DE3238126A1 (ja) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4782071A (en) * | 1986-11-03 | 1988-11-01 | Warner-Lambert Company | Tetrasubstituted urea cholinergic agents |
| DE3832903A1 (de) * | 1987-09-29 | 1989-04-06 | Fuji Photo Film Co Ltd | Elektrophotographische druckplatte |
| US5698262A (en) * | 1996-05-06 | 1997-12-16 | Libbey-Owens-Ford Co. | Method for forming tin oxide coating on glass |
| KR100520180B1 (ko) * | 1999-08-31 | 2005-10-10 | 죌ìíì¬ íìŽëì€ë°ë첎 | í¬í ë ì§ì€ížì ë žêŽí ì§ì° ìì ì±ì í볎íêž° ìí 첚ê°ì |
| EP2328032A3 (en) | 2009-11-27 | 2012-08-15 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, method for producing the same, process cartridge, and electrophotographic apparatus |
| JP5641864B2 (ja) * | 2009-11-27 | 2014-12-17 | ãã€ãã³æ ªåŒäŒç€Ÿ | é»ååçæå äœãé»ååçæå äœã®è£œé æ¹æ³ãããã»ã¹ã«ãŒããªããžããã³é»ååçè£ çœ® |
| JP5725890B2 (ja) * | 2011-02-07 | 2015-05-27 | ãã€ãã³æ ªåŒäŒç€Ÿ | é»ååçè£ çœ® |
| JP5875455B2 (ja) * | 2011-05-24 | 2016-03-02 | ãã€ãã³æ ªåŒäŒç€Ÿ | é»ååçæå äœãããã»ã¹ã«ãŒããªããžãé»ååçè£ çœ®ãé»ååçæå äœã®è£œé æ¹æ³ãåã³ãŠã¬ã¢ååç© |
| JP5680015B2 (ja) | 2011-05-24 | 2015-03-04 | ãã€ãã³æ ªåŒäŒç€Ÿ | é»ååçæå äœãããã»ã¹ã«ãŒããªããžãããã³é»ååçè£ çœ® |
| JP5697629B2 (ja) | 2011-05-24 | 2015-04-08 | ãã€ãã³æ ªåŒäŒç€Ÿ | é»ååçæå äœãé»ååçæå äœã®è£œé æ¹æ³ãããã»ã¹ã«ãŒããªããžããã³é»ååçè£ çœ® |
| JP5546574B2 (ja) | 2011-11-30 | 2014-07-09 | ãã€ãã³æ ªåŒäŒç€Ÿ | é»ååçæå äœãé»ååçæå äœã®è£œé æ¹æ³ãããã»ã¹ã«ãŒããªããžããã³é»ååçè£ çœ® |
| JP5535268B2 (ja) * | 2011-11-30 | 2014-07-02 | ãã€ãã³æ ªåŒäŒç€Ÿ | é»ååçæå äœãé»ååçæå äœã®è£œé æ¹æ³ãããã»ã¹ã«ãŒããªããžããã³é»ååçè£ çœ® |
| JP6218519B2 (ja) * | 2012-10-12 | 2017-10-25 | ãã€ãã³æ ªåŒäŒç€Ÿ | é»ååçæå äœãé»ååçæå äœã®è£œé æ¹æ³ãããã»ã¹ã«ãŒããªããžåã³é»ååçè£ çœ®ã䞊ã³ã«ååç©ãåžçããç²å |
| JP6327981B2 (ja) * | 2014-07-04 | 2018-05-23 | ãã€ãã³æ ªåŒäŒç€Ÿ | é»ååçæå äœãããã»ã¹ã«ãŒããªããžãããã³é»ååçè£ çœ® |
| JP6391400B2 (ja) * | 2014-09-30 | 2018-09-19 | ãã€ãã³æ ªåŒäŒç€Ÿ | é»ååçæå äœãé»ååçæå äœã®è£œé æ¹æ³ãããã»ã¹ã«ãŒããªããžããã³é»ååçè£ çœ® |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3236749A (en) * | 1962-02-13 | 1966-02-22 | Eastman Kodak Co | Single-step direct image-forming electrolytic developer and process for photoconductographic processing |
| US3469979A (en) * | 1965-11-26 | 1969-09-30 | Dennison Mfg Co | Electrophotographic recording element with increased speed |
| US3615404A (en) * | 1968-04-25 | 1971-10-26 | Scott Paper Co | 1 3-phenylenediamine containing photoconductive materials |
| JPS494339B1 (ja) * | 1970-06-10 | 1974-01-31 | ||
| JPS5411737A (en) * | 1977-06-28 | 1979-01-29 | Ricoh Co Ltd | Photoreceptor for electrophotography |
-
1981
- 1981-10-15 JP JP56165260A patent/JPS5865438A/ja active Granted
-
1982
- 1982-10-14 DE DE19823238126 patent/DE3238126A1/de active Granted
- 1982-10-15 US US06/434,695 patent/US4444863A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3238126C2 (ja) | 1989-07-27 |
| JPS5865438A (ja) | 1983-04-19 |
| US4444863A (en) | 1984-04-24 |
| DE3238126A1 (de) | 1983-04-28 |
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