DE3246250C2 - - Google Patents
Info
- Publication number
- DE3246250C2 DE3246250C2 DE3246250A DE3246250A DE3246250C2 DE 3246250 C2 DE3246250 C2 DE 3246250C2 DE 3246250 A DE3246250 A DE 3246250A DE 3246250 A DE3246250 A DE 3246250A DE 3246250 C2 DE3246250 C2 DE 3246250C2
- Authority
- DE
- Germany
- Prior art keywords
- optionally substituted
- weight
- phenyl
- organic photoconductor
- composition according
- 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 substituted alkyl radicals Chemical class 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 25
- 150000003254 radicals Chemical class 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 230000001235 sensitizing effect Effects 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- 206010034972 Photosensitivity reaction Diseases 0.000 claims description 6
- 230000036211 photosensitivity Effects 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 16
- 230000035945 sensitivity Effects 0.000 description 15
- 239000000975 dye Substances 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 229920002799 BoPET Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 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
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229960003540 oxyquinoline Drugs 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group 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
- 206010070834 Sensitisation Diseases 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
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-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
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 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
- 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
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DMDPKUWXJUYFKO-UHFFFAOYSA-N 1,1'-biphenyl;hydrochloride Chemical compound Cl.C1=CC=CC=C1C1=CC=CC=C1 DMDPKUWXJUYFKO-UHFFFAOYSA-N 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
- 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 group C1=CC=CC=C1C1=CC=C(C=C2C(C=CC=C2)=C2)C2=C1C1=CC=CC=C1 OURODNXVJUWPMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 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
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 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
- SQEZMYFOMUVJSU-UHFFFAOYSA-N 1-ethenylacenaphthylene Chemical group C1=CC(C(C=C)=C2)=C3C2=CC=CC3=C1 SQEZMYFOMUVJSU-UHFFFAOYSA-N 0.000 description 1
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-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
- BOIQMNIPQPPTKS-UHFFFAOYSA-N 1-n,4-n-bis(4-chlorophenyl)benzene-1,4-dicarboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=C(C(=O)NC=2C=CC(Cl)=CC=2)C=C1 BOIQMNIPQPPTKS-UHFFFAOYSA-N 0.000 description 1
- LYTXPHIIIZQKMO-UHFFFAOYSA-N 1-n,4-n-bis(4-nitrophenyl)benzene-1,4-dicarboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)C1=CC=C(C(=O)NC=2C=CC(=CC=2)[N+]([O-])=O)C=C1 LYTXPHIIIZQKMO-UHFFFAOYSA-N 0.000 description 1
- MXHDSBYJGVZESK-UHFFFAOYSA-N 1-n,4-n-diphenylbenzene-1,4-dicarboxamide Chemical compound C=1C=C(C(=O)NC=2C=CC=CC=2)C=CC=1C(=O)NC1=CC=CC=C1 MXHDSBYJGVZESK-UHFFFAOYSA-N 0.000 description 1
- BRSRUYVJULRMRQ-UHFFFAOYSA-N 1-phenylanthracene Chemical group C1=CC=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 BRSRUYVJULRMRQ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-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
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical class C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-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
- 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
- CNQGVYDVSJJQCU-UHFFFAOYSA-N 3-chloro-n-(3-chlorophenyl)benzamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C(Cl)C=CC=2)=C1 CNQGVYDVSJJQCU-UHFFFAOYSA-N 0.000 description 1
- QDIUKUHOHYCIRM-UHFFFAOYSA-N 3-chloro-n-phenylbenzamide Chemical compound ClC1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 QDIUKUHOHYCIRM-UHFFFAOYSA-N 0.000 description 1
- IGYJMXLXTJJVRS-UHFFFAOYSA-N 3-nitro-n-(3-nitrophenyl)benzamide Chemical compound [O-][N+](=O)C1=CC=CC(NC(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 IGYJMXLXTJJVRS-UHFFFAOYSA-N 0.000 description 1
- VWIRWLAPFZXYSL-UHFFFAOYSA-N 3-nitro-n-phenylbenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 VWIRWLAPFZXYSL-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
- MOAINDVBLVGJMT-UHFFFAOYSA-N 4-[1-[4-(diethylamino)-2-methylphenyl]-5,5-diphenylpenta-2,4-dienyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)N(CC)CC)C)C=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 MOAINDVBLVGJMT-UHFFFAOYSA-N 0.000 description 1
- BKZSPCUFQFNUIM-UHFFFAOYSA-N 4-[1-[4-(diethylamino)phenyl]-1-phenylethyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C)(C=1C=CC(=CC=1)N(CC)CC)C1=CC=CC=C1 BKZSPCUFQFNUIM-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
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- ANFCIPMWHXLJPQ-UHFFFAOYSA-N n,n-dibenzyl-4-[1-[4-(dibenzylamino)phenyl]butyl]aniline Chemical compound C=1C=C(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(CCC)C(C=C1)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 ANFCIPMWHXLJPQ-UHFFFAOYSA-N 0.000 description 1
- GACNTLAEHODJKY-UHFFFAOYSA-N n,n-dibenzyl-4-[1-[4-(dibenzylamino)phenyl]propyl]aniline Chemical compound C=1C=C(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(CC)C(C=C1)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 GACNTLAEHODJKY-UHFFFAOYSA-N 0.000 description 1
- HFZJMIDOCZBLFI-UHFFFAOYSA-N n,n-dibenzyl-4-[2-[4-(dibenzylamino)phenyl]butan-2-yl]aniline Chemical compound C=1C=C(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(C)(CC)C(C=C1)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 HFZJMIDOCZBLFI-UHFFFAOYSA-N 0.000 description 1
- CTIFEOJGBZUZKN-UHFFFAOYSA-N n,n-dibenzyl-4-[2-[4-(dibenzylamino)phenyl]propan-2-yl]aniline Chemical compound C=1C=C(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 CTIFEOJGBZUZKN-UHFFFAOYSA-N 0.000 description 1
- SBJLRPUTAJENDD-UHFFFAOYSA-N n,n-dibenzyl-4-[4-(dibenzylamino)phenoxy]aniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC(OC=2C=CC(=CC=2)N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC=1)CC1=CC=CC=C1 SBJLRPUTAJENDD-UHFFFAOYSA-N 0.000 description 1
- YVGDNOJCFLHXSC-UHFFFAOYSA-N n,n-dibenzyl-4-[4-(dibenzylamino)phenyl]aniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(CC=1C=CC=CC=1)CC=1C=CC=CC=1)CC1=CC=CC=C1 YVGDNOJCFLHXSC-UHFFFAOYSA-N 0.000 description 1
- MFDMJBQUJWHNHS-UHFFFAOYSA-N n,n-dibenzyl-4-[4-(dibenzylamino)phenyl]sulfanylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC(SC=2C=CC(=CC=2)N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC=1)CC1=CC=CC=C1 MFDMJBQUJWHNHS-UHFFFAOYSA-N 0.000 description 1
- KHKOCWFMKZPYJM-UHFFFAOYSA-N n,n-dibenzyl-4-[[4-(dibenzylamino)phenyl]-diphenylmethyl]aniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC(=CC=1)C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(CC=1C=CC=CC=1)CC=1C=CC=CC=1)CC1=CC=CC=C1 KHKOCWFMKZPYJM-UHFFFAOYSA-N 0.000 description 1
- 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
- CMCSZICPDJMTCF-UHFFFAOYSA-N n-(3-chlorophenyl)-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NC=2C=C(Cl)C=CC=2)=C1 CMCSZICPDJMTCF-UHFFFAOYSA-N 0.000 description 1
- HCMMPLSOWUBZAH-UHFFFAOYSA-N n-(3-chlorophenyl)benzamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=CC=CC=2)=C1 HCMMPLSOWUBZAH-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
- WLUMOMGZPNOSOG-UHFFFAOYSA-N n-(3-nitrophenyl)benzamide Chemical compound [O-][N+](=O)C1=CC=CC(NC(=O)C=2C=CC=CC=2)=C1 WLUMOMGZPNOSOG-UHFFFAOYSA-N 0.000 description 1
- ZJXQWYZBPKDYLS-UHFFFAOYSA-N n-(4-acetylphenyl)benzamide Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)C1=CC=CC=C1 ZJXQWYZBPKDYLS-UHFFFAOYSA-N 0.000 description 1
- PJFPJLMLHHTWDZ-UHFFFAOYSA-N n-(4-chlorophenyl)benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=CC=C1 PJFPJLMLHHTWDZ-UHFFFAOYSA-N 0.000 description 1
- BXZUKYCXOQHJAM-UHFFFAOYSA-N n-(4-cyanophenyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=C(C#N)C=C1 BXZUKYCXOQHJAM-UHFFFAOYSA-N 0.000 description 1
- KEEBHMMBUBEEOV-UHFFFAOYSA-N n-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=CC=C1 KEEBHMMBUBEEOV-UHFFFAOYSA-N 0.000 description 1
- GMGQGZYFQSCZCW-UHFFFAOYSA-N n-(4-nitrophenyl)benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)C1=CC=CC=C1 GMGQGZYFQSCZCW-UHFFFAOYSA-N 0.000 description 1
- ZEVMOCPVPSKFOO-UHFFFAOYSA-N n-benzyl-4-[1-[4-(benzylamino)phenyl]ethyl]aniline Chemical compound C=1C=C(NCC=2C=CC=CC=2)C=CC=1C(C)C(C=C1)=CC=C1NCC1=CC=CC=C1 ZEVMOCPVPSKFOO-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
- BAULSHLTGVOYKM-UHFFFAOYSA-N n-butylbenzamide Chemical compound CCCCNC(=O)C1=CC=CC=C1 BAULSHLTGVOYKM-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
- SDIDYFBTIZOPLA-UHFFFAOYSA-N n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC=C1 SDIDYFBTIZOPLA-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000002245 particle Substances 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 Chemical group 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
- 239000000049 pigment Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004584 polyacrylic acid 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 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
- 150000003246 quinazolines Chemical class 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 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 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 238000000926 separation method Methods 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
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 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
- KHMOASUYFVRATF-UHFFFAOYSA-J tin(4+);tetrachloride;pentahydrate Chemical compound O.O.O.O.O.Cl[Sn](Cl)(Cl)Cl KHMOASUYFVRATF-UHFFFAOYSA-J 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
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- JLKZUNOWPPEBPX-UHFFFAOYSA-N zinc;3h-1,3-benzothiazole-2-thione Chemical compound [Zn+2].C1=CC=C2SC(=S)NC2=C1 JLKZUNOWPPEBPX-UHFFFAOYSA-N 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
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0503—Inert supplements
- G03G5/051—Organic non-macromolecular compounds
- G03G5/0517—Organic non-macromolecular compounds comprising one or more cyclic groups consisting of carbon-atoms 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
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0503—Inert supplements
- G03G5/051—Organic non-macromolecular compounds
- G03G5/0514—Organic non-macromolecular compounds not comprising cyclic groups
-
- 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
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0503—Inert supplements
- G03G5/051—Organic non-macromolecular compounds
- G03G5/0521—Organic non-macromolecular compounds comprising one or more heterocyclic groups
-
- 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
-
- 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)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56201306A JPS58102239A (ja) | 1981-12-14 | 1981-12-14 | 光導電性組成物およびそれを用いた電子写真感光材料 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3246250A1 DE3246250A1 (de) | 1983-06-16 |
| DE3246250C2 true DE3246250C2 (en, 2012) | 1988-09-08 |
Family
ID=16438810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823246250 Granted DE3246250A1 (de) | 1981-12-14 | 1982-12-14 | Photoleitfaehige zusammensetzungen und elektrophotographische aufzeichnungsmaterialien |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4499167A (en, 2012) |
| JP (1) | JPS58102239A (en, 2012) |
| DE (1) | DE3246250A1 (en, 2012) |
| GB (1) | GB2114761B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3329441A1 (de) * | 1983-08-16 | 1985-03-21 | Hoechst Ag, 6230 Frankfurt | Elektrophotographisches aufzeichnungsmaterial und verfahren zu seiner herstellung |
| DE3329442A1 (de) * | 1983-08-16 | 1985-03-21 | Hoechst Ag, 6230 Frankfurt | Elektrophotographisches aufzeichnungsmaterial und verfahren zu seiner herstellung |
| DE3630389C2 (de) * | 1985-09-05 | 1998-04-16 | Fuji Photo Film Co Ltd | Elektrophotographisches lichtempfindliches Aufzeichnungsmaterial |
| DE3832903A1 (de) * | 1987-09-29 | 1989-04-06 | Fuji Photo Film Co Ltd | Elektrophotographische druckplatte |
| JPH01137260A (ja) * | 1987-11-25 | 1989-05-30 | Fuji Photo Film Co Ltd | 電子写真感光体 |
| TW457403B (en) * | 1998-07-03 | 2001-10-01 | Clariant Int Ltd | Composition for forming a radiation absorbing coating containing blocked isocyanate compound and anti-reflective coating formed therefrom |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL99369C (en, 2012) * | 1956-06-04 | |||
| JPS56138742A (en) * | 1980-03-31 | 1981-10-29 | Konishiroku Photo Ind Co Ltd | Charge retaining material and method for forming copy image using this material |
| US4399206A (en) * | 1980-10-06 | 1983-08-16 | Canon Kabushiki Kaisha | Disazo electrophotographic photosensitive member |
-
1981
- 1981-12-14 JP JP56201306A patent/JPS58102239A/ja active Granted
-
1982
- 1982-12-13 GB GB08235454A patent/GB2114761B/en not_active Expired
- 1982-12-14 DE DE19823246250 patent/DE3246250A1/de active Granted
- 1982-12-14 US US06/449,729 patent/US4499167A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3246250A1 (de) | 1983-06-16 |
| US4499167A (en) | 1985-02-12 |
| JPH0225504B2 (en, 2012) | 1990-06-04 |
| GB2114761B (en) | 1985-08-29 |
| GB2114761A (en) | 1983-08-24 |
| JPS58102239A (ja) | 1983-06-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: BARZ, P., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 80803 MUENCHEN |
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| 8339 | Ceased/non-payment of the annual fee |