US3617268A - Electrophotographic materials - Google Patents
Electrophotographic materials Download PDFInfo
- Publication number
- US3617268A US3617268A US4200A US3617268DA US3617268A US 3617268 A US3617268 A US 3617268A US 4200 A US4200 A US 4200A US 3617268D A US3617268D A US 3617268DA US 3617268 A US3617268 A US 3617268A
- Authority
- US
- United States
- Prior art keywords
- solution
- sensitizer
- compound
- vinylcarbazole
- methoxystyryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000463 material Substances 0.000 title claims abstract description 30
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 15
- OPMONMBXTLWESE-UHFFFAOYSA-M 2-[2-(4-methoxyphenyl)ethenyl]-3-phenylchromenylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC(OC)=CC=C1C=CC(C(=C1)C=2C=CC=CC=2)=[O+]C2=C1C=CC=C2 OPMONMBXTLWESE-UHFFFAOYSA-M 0.000 claims description 3
- CSMWYVFOQHXFMR-UHFFFAOYSA-M 2-phenylchromenylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=[O+]1 CSMWYVFOQHXFMR-UHFFFAOYSA-M 0.000 claims description 2
- CLWNSPKQLPJJCF-UHFFFAOYSA-M 3-phenyl-2-(2-phenylethenyl)chromenylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C=1C=CC=CC=1C=CC1=[O+]C=2C=CC=CC=2C=C1C1=CC=CC=C1 CLWNSPKQLPJJCF-UHFFFAOYSA-M 0.000 claims description 2
- UMBRQIDTMFCMIH-UHFFFAOYSA-N 4-methoxy-3-phenyl-2-(2-phenylethenyl)-2H-chromene Chemical compound C(=CC1=CC=CC=C1)C1OC2=C(C(=C1C1=CC=CC=C1)OC)C=CC=C2 UMBRQIDTMFCMIH-UHFFFAOYSA-N 0.000 claims description 2
- ZBOGHZVCYDRZMC-UHFFFAOYSA-M 2-(4-methoxyphenyl)chromenylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC(OC)=CC=C1C1=CC=C(C=CC=C2)C2=[O+]1 ZBOGHZVCYDRZMC-UHFFFAOYSA-M 0.000 claims 2
- ZLIVHWCHPQOGBT-UHFFFAOYSA-N 4-methoxy-2-[2-(4-methoxyphenyl)ethenyl]-3-phenyl-2H-pyran Chemical compound COC1=CC=C(C=CC2OC=CC(=C2C2=CC=CC=C2)OC)C=C1 ZLIVHWCHPQOGBT-UHFFFAOYSA-N 0.000 claims 2
- MJOGGIWZLNPBCS-UHFFFAOYSA-N 4-methoxy-2-(4-methoxyphenyl)-2H-chromene Chemical compound COC1=CC=C(C=C1)C1OC2=C(C(=C1)OC)C=CC=C2 MJOGGIWZLNPBCS-UHFFFAOYSA-N 0.000 claims 1
- SXXKUCVHZMMFIY-UHFFFAOYSA-N 4-methoxy-2-phenyl-2h-chromene Chemical compound O1C2=CC=CC=C2C(OC)=CC1C1=CC=CC=C1 SXXKUCVHZMMFIY-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 43
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 abstract description 17
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 abstract description 13
- 239000000243 solution Substances 0.000 description 55
- 238000000034 method Methods 0.000 description 30
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 13
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
- -1 Z-(p-methoxystyryl)-3-phenyl-4-methoxypyrane Chemical compound 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 125000005504 styryl group Chemical group 0.000 description 6
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000011810 insulating material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 150000001562 benzopyrans Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000019241 carbon black Nutrition 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RXHNUHOTGHFNIC-UHFFFAOYSA-N 2-(4-methoxyphenyl)chromenylium Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=CC=C2)C2=[O+]1 RXHNUHOTGHFNIC-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- UFMXDHRCBVAFQR-UHFFFAOYSA-N 4-methoxy-2-[2-(4-methoxyphenyl)ethenyl]-3-phenyl-2h-chromene Chemical compound O1C2=CC=CC=C2C(OC)=C(C=2C=CC=CC=2)C1C=CC1=CC=C(OC)C=C1 UFMXDHRCBVAFQR-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000999 acridine dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- HRYZWHHZPQKTII-ZDOIIHCHSA-N chloroethane Chemical class [13CH3][13CH2]Cl HRYZWHHZPQKTII-ZDOIIHCHSA-N 0.000 description 1
- CHZWRIFDYXSVOD-UHFFFAOYSA-M chromenylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.[O+]1=CC=CC2=CC=CC=C21 CHZWRIFDYXSVOD-UHFFFAOYSA-M 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000615 nonconductor Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012063 pure reaction product Substances 0.000 description 1
- NTQLADLBRQMNQJ-UHFFFAOYSA-M pyrylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC=[O+]C=C1 NTQLADLBRQMNQJ-UHFFFAOYSA-M 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000001003 triarylmethane dye Substances 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
- G03G5/0637—Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
Definitions
- a photosensitive material for electrophotography comprising an organic photoconductive compound and a sensitizer consisting of reaction products of a benzopyrylium salt and a benzopyrane.
- This invention relates to an electrophotographic material and more particularly to a photoconductive insulating material comprising an organic photoconductive compound and a sensitizer.
- photoconductive insulating layers are well known in the electrophotographic art for making copies of documents, drawings, transparencies, etc. These layers contain on organic photoconductive compound, such as poly-N-vinylcarbazole, poly-3,6-dibromo-N-vinylcarbazole, brominated poly- N-vinylcarbazole, nitrated poly-N-vinylcarbazole, polyacenaphthylene, etc. These layers are nonconductors of electricity before exposure and become electrical conductors upon exposure.
- the photoconductive insulating material has a high photoconductivity in the region of the visible spectrum.
- Such a photoconductive insulating material makes it possible for the electrophotographic art to employ inexpensive and convenient light sources such as incandescent lamps in a reduced exposure time and to reproduce colored pictures.
- the photoconductive compounds mentioned above however, have usually a low photoconductivity and spectrum characteristics sensitive to the short wavelength region of the exposure light and do not satisfy entirely the above requirement.
- sensitizer can improve photoconductivity and spectrum response of the above photoconductive compounds.
- Conventional sensitizers are dyestuffs, such as triarylmethane dyes, xanthene dyes, triazine dyes or acridine dyes, but the conventional sensitizers are-not entirely satisfactory for improvement of the photoconductivity and the spectrum response of the available organic photoconductive compounds.
- the electrophotographic art requires a high electric resistance of photoconductive materials in the dark.
- Conventional sensitizers promote the photoconductivity but increase the dark conductivity.
- a high dark conductivity of photoconductive materials is not desirable because it results in a loss of the applied electrostatic charge in the dark.
- Another object of the invention is to provide electrophotographic materials having a high electric resistance in the dark.
- FIG. 1 represents the absorption spectra, in 1,2- dichloroethane, of one example (Sample Number 27) of sensitizers according to the present invention under comparison with those of 2-(p-methoxystyryl)-3-phenylbenzopyrylium perchlorate (Compound Number 2), in 1,2-dichloroethane, and Z-(p-methoxystyryl)-3-phenyl-4-methoxypyrane (Compound Number ll) in methanol.
- FIG. 2 represents the infrared absorption spectra in KBr method ofCompound Number 2, 11 and Sample Number 27.
- FIG. 3 represents the wedge spectrogram for an electrophotographic material coated with a solution containing weight percent of brominated poly-n-vinylcarbazole and 0.02 weight percent of sensitizer (Sample Number 27), the brominated poIy-N-vinylcarbazole being dissolved in a solvent consisting of4 parts by weight of chlorobenzene and 1 part by weight of 1,2-dichloroethane under comparison with those of brominated poly-N-vinylcarbazole.
- FIG. 4 represents the wedge spectrogram of an electrophotographic material coated with a 10 weight percent solution of brominated poly-N-Vinylcarbazole sensitized with 0.02 weight of Sample Number 50, the brominated poly-N- vinylcarbazole being dissolved in a solvent consisting of 4 parts by weight of chlorobenzene and 1 part by weight of 1,2- dichloroethane, under comparison with the wedge spectrogram of an electrophotographic material coated with a 10 weight percent solution of brominated poly-N-vinylcarbazole sensitized with 0.06 weight percent of Compound Number 9, which is the raw material of Sample Number 50, the brominated poly-N-vinylcarbazole being dissolved in a solvent consisting of 4 parts by weight of chlorobenzene and 1 part by weight of 1,2-dichloroethane.
- FIG. 5 represents the wedge spectrogram of an electrophotographic material coated with a 10 weight percent solution of poly-N-vinylcarbazole sensitized with 0.03 weight percent of Sample Number 39, the poly-N-vinylcarbazole being dissolvedin a solvent consisting of 4 parts by weight of toluene and 1 part by weight of l,2-dichloroethane.
- FIG. 6 represents the wedge spectrogram of an electrophotographic material coated with l0 weight percent solution of poly-N-vinylcarbazole sensitized with 0.03 weight percent of Sample Number 28, the poly-N-vinylcarbazole being dissolved in a solvent consisting of 4 parts by weight of toluene and 1 part by weight of l,2-dichloroethane.
- R is an aliphatic group such as styryl, p-methoxystyryl, w-phenylbutadienyl; aromatic group such as phenyl, pmethoxyphenyl;
- R is selected from the group consisting of hydrogen and phenyl radical
- R is selected from the group consisting of hydrogen and methoxy radical
- Anion is fluoborate chloroferrate, perchlorate anion.
- the chemical formula B is chlorozincate or /O -RI l L...
- R is an aliphatic group such as styryl, p-methoxystyryl,
- R is selected from the group consisting of hydrogen and phenyl radical
- R is selected from the group consisting of hydrogen and methoxy radical.
- Said reaction products can be formed by employing the following steps which comprise (1) providing a solution of said benzopyrylium salt in a suitable solvent such as 1,2- dichloroethane, (2) providing a solution of said benzopyrane in a suitable solvent such as l,2-dichloroethane, (3) mixing both solutions and heating the mixed solution (4) pouring the heated solution into a suitable precipitant such as ether to form a precipitate separating the precipitate from the precipitant and (6) purifying the separated precipitate.
- the first method is a modification of a method disclosed in J. Chem. Soc.. i935, page 941 and is based on the reaction of a phenol or phenol derivative with a B-dicarbonyl compound or an a,B-unsaturated ketone in the presence of hydrogen chloride, sulfuric acid, ferric chloride, acetic or formic acid.
- the second method comprises using an intermediate product prepared from a phenol and a coumarin derivative in the presence of phosphorus oxychloride or zinc chloride in a similar way to that disclosed in Helv. chim. acta, 34, page 1761 (1951).
- the third method is based on a method disclosed in J. Chem. Soc., 74, page 3,445 (1952).
- a ring closure process of an o-hydroxybenzaldehyde and a carbonyl compound in the presence of an alkali forms a benzopyrylium ring.
- An ethenyl group of an active a-methylene radical in the 2-position of 2- alkylbenzopyrylium has an important role on the benzopyrylium ring closure process.
- the fourth method is based on a method disclosed in J. Chem. Soc., 1929, page 936 and is effected in one step by both ring closure and ethenylation of an o-hydroxybenzaldehyde with a carbonyl compound in the presence of an alkali.
- BENZOPYRANE The benzopyranes are easily prepared by one of the following two methods.
- a first method is that benzopyrane is prepared by heating, under a reflux, a methanol solution of said benzopyrylium salt with sodium bicarbonate.
- a second method is that benzopyrane is prepared by heating an alcohol solution of said benzopyrylium salt with sodium hydroxide or potassium hydroxide.
- the crude compound filtered off is dissolved in 500 milliliters of methanol under heating in order to obtain a solution, then, the solution is cooled, added 500 milliliters of water and allowed to stand overnight. The resulting precipitate having a melting point of 84 to 86 C. is then collected by filtration.
- the benzopyrane thus obtained is unstable and tends to change to a benzopyrylium salt by adding organic acid or inorganic acid. Furthermore, the benzopyrane is colored by air. Therefore, an improved preparation procedure is developed as follows: in the preparation procedure such as procedure (3) or (4), the crude benzopyrane is not recrystallized from a methanol-water solution, but the crude compound is shaken in SENSITIZER
- the sensitizer according to the present invention is produced by the reaction of a benzopyrylium salt and a benzopyrane. Examples of the reaction products are shown in table 3 with their physical properties.
- sensitizer is accomplished by heating a solution of the benzopyrylium salt and benzopyrane in a suitable solvent such as dichloroethane at 40 to 70 C. for several hours to dozens of hours.
- a suitable solvent such as dichloroethane at 40 to 70 C.
- the amount of benzopyrane to be used is oneto three times by molar weight of benzopyrylium salt to be used.
- the color of the solution changes to dark color with a progress of the reaction. For example, FIG.
- sensitizers Some examples of methods of preparing the sensitizer are set forth below in accordance with table 3. It will be apparent to those skilled in the art that other sensitizers according to the present invention may be prepared by methods similar to those described in general hereinabove and specifically herein below.
- Sample Number 39 3.4 grams of Compound Number 13 and 2 grams of Compound Number 6 are dissolved in 75 milliliters of 1,2- dichloroethane which is purified to eliminate an acidic material. A so-obtained solution is stirred at 50 C. for 8 hours. After the same procedure as stated in (l), 3 grams of crystal is the yield. The crystal has a melting point of l70 to 174 C. and a solution of the crystal in 1,2-dichloroethane is green.
- An improved photoconductive insulating material adapted for aforesaid photoconductive insulating layer can be obtained by a combination of aforesaid sensitizer and aforesaid organic photoconductive compound selected from the group consisting of poly-N-vinylcarbazole, poly-3,6-dibromo-N- vinylcarb'azole, brominated poly-N-vinylcarbazole, nitrated poly-N-vinylcarbazole and polyacenaphthylene.
- the sensitizer according to the present invention is usually added to a solution of the'phot'oconductive compound in the form of a solution in a suitable solvent, such as dichloroethane, methylene chloride, chloroform, or a combination thereof.
- a suitable solvent such as dichloroethane, methylene chloride, chloroform, or a combination thereof.
- An added amount of said sensitizer is from 0.005 gram to 0.02 gram, preferably from 0.00l5 gram to 0.015 gram with respect to 1 gram ofsaid organic photoconductive compound.
- Poly-3,6 dibromo-N-vinylcarbazole and brominated poly- Nvinylcarbazole'are prepared by the methods described in U.S. Pat. No: 3,421 .891.
- Nitrated poly-N-vinylcarbazole is prepared by the method described in U.S. Pat. No. 3,418,116.
- Other polymers are prepared by well-known methods.
- a solution of the photoconductive polymer and the sensitizer in a suitable solvent is applied to the supports in the usual manner, for example, spraying, blade coating, wire-rod" coating or whirler coating, and then dried so as to produce a homogeneous photoconductive insulating layer on the electroconductive support.
- suitable solvents are benzene, toluene, chlorobenzene, dioxane, methylene chloride, dichloroethane and combinations thereof.
- the solution may include suitable plasticizers and/or organic colloids for improving the flexibility and strength of the photoconductive compound layer.
- Suitable plasticizers include chlorinated diphenyl, dimethyl phthalate, diethyl phthalate and octyl phthalate.
- Suitable organic colloids include natural and synthetic resins, e.g. phenol resin, phenol resin modified wit h rosin polyvinyl acetal, polyvinyl butyral, polyvinyl cinnamate and polycarbonate resin.
- Suitable materials for a conductive support layer are those materials which satisfy the requirement of the electrophotographic art and include metal plates, glass plates having NESA coating and plates or foils made of electrically conductive resins or coated with a vacuum-deposited thin metal layer.
- Transparent supports can be used to form transparent .electrophotographic plates, foils or films.
- the reproduction of images by electrophotographic ,methods is carried out as follows: when the photoconductive insulating layer has been charged by means of a corona discharge apparatus, the electrophotographic material with the photoconductive insulating layer is exposed to light under a master and is then dusted over in a known manner with a resin powder colored with carbon black. The image that now becomes visible can easily be wiped off. It can also be fixed by heating at about 120 C. From positive masters, positive images exhibiting good contrast are produced.
- EXAMPLE 1 One gram of poly-N-vinylcarbazole, 0.004 gram of a sensitizer listed in table 3 and 0.5 gram of chlorinated diphenyl (commercially available as Kanechlor") are dissolved in 10 milliliters of l,2-dichloroethane. The solution is applied to an aluminum plate and is dried to form a layer [p in thickness. After the aluminum plate provided with the layer is charged positively by means of corona discharge with a charging device maintained at approximately 6,000 volts in the dark, it is placed under a positive master and is exposed to a l00 W tungsten lamp at an illumination of 50 luxes. Subsequently, the plate is powdered over with a developer in a per se known manner.
- the toner consists of a low melting-point polystyrene, colophony and carbon-black and is mixed with a carrier substance having a nature such that the toner becomes triboelectrically charged with a charge opposite to that produced on the plate.
- a positive image is produced and is fixed by slight heating.
- Table 4 shows the optimum amounts of exposure in lux-second units.
- EXAMPLE 2 One gram of polyacenaphthylene. 0.6 gram of chlorinated diphenyl (commercially available as Kanechlor) and 0.004 gram of a sensitizer listed in table 3 are dissolved in 10 milliliters of l,2-dichloroethane The solution is applied to an aluminum plate and is dried to form a layer 6;; in thickness. An
- electrophotographic image is produced in the same way as that described in example 1.
- Table 5 shows the optimum amounts of exposure in lux-second units to produce exactly the original images.
- Applicants preferred sensitizing compounds are those selected from the reaction products of a benzopyrylium salt having the chemical formula T Anionwherein R is a'radical selected from thejgroup consisting of a- -isopropyl-w-phenylbutadienyl, methoxystyryl, methoxyphenyl, styryl, a-isopropyl methoxystyryl a-isopropylstyryl and .phenyl,
- R is hydrogen or phenyl
- R is hydrogen or methoxy
- R is aradical selected from the group consisting of styryl, methoxystyrl, a-isopropyl-m-phenylbutadienyl. aisopropyl-methoxystyryl, phenyl, a-isopropyl styryl and methoxyphenyl,
- R is hydrogen or phenyl
- R is hydrogen or methoxy.
- An electrophotographic material comprising a conductive support layer and a 'photoconductive in'sulating'layer, the latter comprising a combination of an organic photoconductive compound :and a sensitizer, said organic photoconductive compound consisting essentially of at least one compound selected from the group consisting of poly-N-vinylcarbazole, poly-3,6-dibromo-N-vinylcarbazole, brominated poly-N-vinylcarbazole, nitrated poly-N-vinylcarbazole and polyacenaphthylene, said sensitizer comprising a compound selected from the group consisting of reaction products of a l)enzopyryliunisalt ha ving the chemical formula I I Anionwherein R is a radical selected from the group consisting of aisopropyl-wphenylbutadienyl, methoxystyryl, methoxyphenyl, styryl, a-isopropyl methoxys
- R is a radical selected from the group consisting of styryl. methoxystryl a-isopropyl-w-phenylbutadienyl. aisopropyl-methoxystyryl, phenyl, a-isopropyl styryl and methoxyphenyl,
- R is hydrogen or phenyl
- R is hydrogen or methoxy.
- the electrophotographic material of claim 1 wherein the sensitizer is the reaction product of Z-(a-isopropyl-w-phenylbutadienyl)-benzopyrylium perchlorate and Z-(p-methoxystyryl)-3-phenyl-4-methoxypyranev 3.
- the electrophotographic material of claim 1 wherein the sensitizer is the reaction product of 2- p-methoxystyryl)-3 phenyl-benzopyrylium perchlorate and -(p-methoxystyryl)- 3-phenyl-4-methoxypyrane.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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JP44007501A JPS4825658B1 (US07489958-20090210-P00001.png) | 1969-01-30 | 1969-01-30 |
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US3617268A true US3617268A (en) | 1971-11-02 |
Family
ID=11667513
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US4200A Expired - Lifetime US3617268A (en) | 1969-01-30 | 1970-01-20 | Electrophotographic materials |
Country Status (6)
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3881924A (en) * | 1971-08-25 | 1975-05-06 | Matsushita Electric Ind Co Ltd | Organic photoconductive layer sensitized with trimethine compound |
US3896112A (en) * | 1971-10-21 | 1975-07-22 | Ricoh Kk | Bisbenzopyran and bisbenzopyrylium adducts |
US3912508A (en) * | 1970-10-07 | 1975-10-14 | Matsushita Electric Ind Co Ltd | Electrophotographic element comprising an organic photoconductive layer sensitized locally at its surface |
USRE28698E (en) * | 1970-03-13 | 1976-01-27 | Matsushita Electric Industrial Co., Ltd. | Electrophotographic material containing sensitizers |
US3938994A (en) * | 1972-03-17 | 1976-02-17 | Eastman Kodak Company | Pyrylium dyes for electrophotographic composition and element |
US3953433A (en) * | 1971-06-22 | 1976-04-27 | Ricoh Co., Ltd. | Sensitizer for use in electrophotographic light-sensitive material |
US4283475A (en) * | 1979-08-21 | 1981-08-11 | Fuji Photo Film Co., Ltd. | Pentamethine thiopyrylium salts, process for production thereof, and photoconductive compositions containing said salts |
DE3331592A1 (de) | 1982-09-01 | 1984-03-01 | Fuji Photo Film Co., Ltd., Minamiashigara, Kanagawa | Disazoverbindungen und diese enthaltende photoleitfaehige zusammensetzungen und elektrophotographische lichtempfindliche aufzeichnungsmaterialien |
US4476313A (en) * | 1982-04-02 | 1984-10-09 | Rensselaer Polytechnic Institute | Pyrylium salts |
US5405976A (en) * | 1990-11-21 | 1995-04-11 | Polaroid Corporation | Benzpyrylium squarylium and croconylium dyes, and processes for their preparation and use |
US5753695A (en) * | 1992-09-21 | 1998-05-19 | Biogal Gyogyszergyar Rt | Flavilium compounds and method of using |
US5977351A (en) * | 1990-11-21 | 1999-11-02 | Polaroid Corporation | Benzpyrylium squarylium and croconylium dyes, and processes for their preparation and use |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3250615A (en) * | 1961-10-23 | 1966-05-10 | Eastman Kodak Co | Light-sensitive layers containing pyrylium and thiapyrylium salts |
US3526502A (en) * | 1966-07-18 | 1970-09-01 | Matsushita Electric Ind Co Ltd | Electrophotographic material |
-
1969
- 1969-01-30 JP JP44007501A patent/JPS4825658B1/ja active Pending
-
1970
- 1970-01-20 US US4200A patent/US3617268A/en not_active Expired - Lifetime
- 1970-01-28 FR FR7002995A patent/FR2029686A1/fr active Pending
- 1970-01-28 GB GB4086/70A patent/GB1244582A/en not_active Expired
- 1970-01-29 DE DE2004766A patent/DE2004766B2/de active Granted
- 1970-01-30 NL NL707001389A patent/NL142250B/xx not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3250615A (en) * | 1961-10-23 | 1966-05-10 | Eastman Kodak Co | Light-sensitive layers containing pyrylium and thiapyrylium salts |
US3526502A (en) * | 1966-07-18 | 1970-09-01 | Matsushita Electric Ind Co Ltd | Electrophotographic material |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USRE28698E (en) * | 1970-03-13 | 1976-01-27 | Matsushita Electric Industrial Co., Ltd. | Electrophotographic material containing sensitizers |
US3912508A (en) * | 1970-10-07 | 1975-10-14 | Matsushita Electric Ind Co Ltd | Electrophotographic element comprising an organic photoconductive layer sensitized locally at its surface |
US3953433A (en) * | 1971-06-22 | 1976-04-27 | Ricoh Co., Ltd. | Sensitizer for use in electrophotographic light-sensitive material |
US3881924A (en) * | 1971-08-25 | 1975-05-06 | Matsushita Electric Ind Co Ltd | Organic photoconductive layer sensitized with trimethine compound |
US3896112A (en) * | 1971-10-21 | 1975-07-22 | Ricoh Kk | Bisbenzopyran and bisbenzopyrylium adducts |
US3938994A (en) * | 1972-03-17 | 1976-02-17 | Eastman Kodak Company | Pyrylium dyes for electrophotographic composition and element |
US4283475A (en) * | 1979-08-21 | 1981-08-11 | Fuji Photo Film Co., Ltd. | Pentamethine thiopyrylium salts, process for production thereof, and photoconductive compositions containing said salts |
US4476313A (en) * | 1982-04-02 | 1984-10-09 | Rensselaer Polytechnic Institute | Pyrylium salts |
DE3331592A1 (de) | 1982-09-01 | 1984-03-01 | Fuji Photo Film Co., Ltd., Minamiashigara, Kanagawa | Disazoverbindungen und diese enthaltende photoleitfaehige zusammensetzungen und elektrophotographische lichtempfindliche aufzeichnungsmaterialien |
US5405976A (en) * | 1990-11-21 | 1995-04-11 | Polaroid Corporation | Benzpyrylium squarylium and croconylium dyes, and processes for their preparation and use |
US5627014A (en) * | 1990-11-21 | 1997-05-06 | Polaroid Corporation | Benzpyrylium squarylium and croconylium dyes, and processes for their preparation and use |
US5977351A (en) * | 1990-11-21 | 1999-11-02 | Polaroid Corporation | Benzpyrylium squarylium and croconylium dyes, and processes for their preparation and use |
US5753695A (en) * | 1992-09-21 | 1998-05-19 | Biogal Gyogyszergyar Rt | Flavilium compounds and method of using |
Also Published As
Publication number | Publication date |
---|---|
NL7001389A (US07489958-20090210-P00001.png) | 1970-08-03 |
DE2004766A1 (de) | 1970-07-30 |
NL142250B (nl) | 1974-05-15 |
GB1244582A (en) | 1971-09-02 |
DE2004766B2 (de) | 1974-01-24 |
JPS4825658B1 (US07489958-20090210-P00001.png) | 1973-07-31 |
FR2029686A1 (US07489958-20090210-P00001.png) | 1970-10-23 |
DE2004766C3 (US07489958-20090210-P00001.png) | 1974-08-15 |
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