CA1104866A - Imaging member containing a substituted n,n,n',n',- tetraphenyl-[1,1'-biphenyl]-4,4'-diamine in the chargge transport layer - Google Patents
Imaging member containing a substituted n,n,n',n',- tetraphenyl-[1,1'-biphenyl]-4,4'-diamine in the chargge transport layerInfo
- Publication number
- CA1104866A CA1104866A CA281,674A CA281674A CA1104866A CA 1104866 A CA1104866 A CA 1104866A CA 281674 A CA281674 A CA 281674A CA 1104866 A CA1104866 A CA 1104866A
- Authority
- CA
- Canada
- Prior art keywords
- layer
- selenium
- photoconductive
- holes
- charge
- 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
- 238000003384 imaging method Methods 0.000 title claims description 18
- 238000002347 injection Methods 0.000 claims abstract description 17
- 239000007924 injection Substances 0.000 claims abstract description 17
- 239000004431 polycarbonate resin Substances 0.000 claims abstract description 15
- 229920005668 polycarbonate resin Polymers 0.000 claims abstract description 13
- 230000003595 spectral effect Effects 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims description 69
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 54
- 229910052711 selenium Inorganic materials 0.000 claims description 54
- 239000011669 selenium Substances 0.000 claims description 54
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 26
- 229920000515 polycarbonate Polymers 0.000 claims description 24
- 239000004417 polycarbonate Substances 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 21
- 229910052785 arsenic Inorganic materials 0.000 claims description 15
- 229910001370 Se alloy Inorganic materials 0.000 claims description 7
- QLNFINLXAKOTJB-UHFFFAOYSA-N [As].[Se] Chemical compound [As].[Se] QLNFINLXAKOTJB-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052714 tellurium Inorganic materials 0.000 claims description 5
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- HILYGPZEXFJYJQ-UHFFFAOYSA-N 3-chloro-n-[4-[4-(n-(3-chlorophenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound ClC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(Cl)C=CC=2)=C1 HILYGPZEXFJYJQ-UHFFFAOYSA-N 0.000 claims 1
- FZNNXLWLZUHEHG-UHFFFAOYSA-N n-(4-chlorophenyl)-4-[4-(n-(4-chlorophenyl)anilino)phenyl]-n-phenylaniline Chemical compound C1=CC(Cl)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 FZNNXLWLZUHEHG-UHFFFAOYSA-N 0.000 claims 1
- 230000032258 transport Effects 0.000 abstract description 69
- 238000011161 development Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 252
- 239000011230 binding agent Substances 0.000 description 34
- 239000000758 substrate Substances 0.000 description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000002245 particle Substances 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 24
- -1 poly(N-vinylcarbazole) Polymers 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 150000004985 diamines Chemical class 0.000 description 15
- 239000004305 biphenyl Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 229910052736 halogen Inorganic materials 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 12
- 239000002800 charge carrier Substances 0.000 description 12
- 229940090044 injection Drugs 0.000 description 12
- 230000005855 radiation Effects 0.000 description 12
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 108091008695 photoreceptors Proteins 0.000 description 8
- 229940093956 potassium carbonate Drugs 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 239000012260 resinous material Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 101150041968 CDC13 gene Proteins 0.000 description 7
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- 239000004418 Lexan Substances 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 239000011149 active material Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 238000011068 loading method Methods 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000003213 activating effect Effects 0.000 description 5
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 229910003480 inorganic solid Inorganic materials 0.000 description 4
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- 239000000049 pigment Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-UHFFFAOYSA-N 0.000 description 3
- 239000004425 Makrolon Substances 0.000 description 3
- 229910052770 Uranium Inorganic materials 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000001351 cycling effect Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000007812 deficiency Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 230000011514 reflex Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- JMLWXCJXOYDXRN-UHFFFAOYSA-N 1-chloro-3-iodobenzene Chemical compound ClC1=CC=CC(I)=C1 JMLWXCJXOYDXRN-UHFFFAOYSA-N 0.000 description 2
- GWQSENYKCGJTRI-UHFFFAOYSA-N 1-chloro-4-iodobenzene Chemical compound ClC1=CC=C(I)C=C1 GWQSENYKCGJTRI-UHFFFAOYSA-N 0.000 description 2
- OOLSRHZMXAYDFB-UHFFFAOYSA-N 1-ethyl-4-iodobenzene Chemical compound CCC1=CC=C(I)C=C1 OOLSRHZMXAYDFB-UHFFFAOYSA-N 0.000 description 2
- RINOYHWVBUKAQE-UHFFFAOYSA-N 1-iodo-2-methylbenzene Chemical compound CC1=CC=CC=C1I RINOYHWVBUKAQE-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910000967 As alloy Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 101100459301 Mus musculus Myl4 gene Proteins 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000009056 active transport Effects 0.000 description 2
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- PGWFQHBXMJMAPN-UHFFFAOYSA-N ctk4b5078 Chemical compound [Cd].OS(=O)(=O)[Se]S(O)(=O)=O PGWFQHBXMJMAPN-UHFFFAOYSA-N 0.000 description 2
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- BXIHNKAABXMVNA-UHFFFAOYSA-N 1-benzhydryl-2,3-dimethylbenzene Chemical compound CC1=CC=CC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C BXIHNKAABXMVNA-UHFFFAOYSA-N 0.000 description 1
- XILRUONFYBUYIE-UHFFFAOYSA-N 1-butyl-4-iodobenzene Chemical compound CCCCC1=CC=C(I)C=C1 XILRUONFYBUYIE-UHFFFAOYSA-N 0.000 description 1
- XSMZGZMBNXKCBW-UHFFFAOYSA-N 1-ethyl-3-iodobenzene Chemical compound CCC1=CC=CC(I)=C1 XSMZGZMBNXKCBW-UHFFFAOYSA-N 0.000 description 1
- VLCPISYURGTGLP-UHFFFAOYSA-N 1-iodo-3-methylbenzene Chemical compound CC1=CC=CC(I)=C1 VLCPISYURGTGLP-UHFFFAOYSA-N 0.000 description 1
- OFAPSLLQSSHRSQ-UHFFFAOYSA-N 1H-triazine-2,4-diamine Chemical class NN1NC=CC(N)=N1 OFAPSLLQSSHRSQ-UHFFFAOYSA-N 0.000 description 1
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- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 1
- FBARBMWUOUNTMI-UHFFFAOYSA-N 4-[4-(3-methylanilino)phenyl]-n-(3-methylphenyl)-2,3-diphenylaniline Chemical compound CC1=CC=CC(NC=2C=CC(=CC=2)C=2C(=C(C=3C=CC=CC=3)C(NC=3C=C(C)C=CC=3)=CC=2)C=2C=CC=CC=2)=C1 FBARBMWUOUNTMI-UHFFFAOYSA-N 0.000 description 1
- WXAIEIRYBSKHDP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)-n-[4-[4-(4-phenyl-n-(4-phenylphenyl)anilino)phenyl]phenyl]aniline Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 WXAIEIRYBSKHDP-UHFFFAOYSA-N 0.000 description 1
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- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 239000011140 metalized polyester Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 230000037230 mobility Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000003748 selenium group Chemical group *[Se]* 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000005109 triphenodioxazines Chemical class 0.000 description 1
- KOTVVDDZWMCZBT-UHFFFAOYSA-N vat violet 1 Chemical compound C1=CC=C[C]2C(=O)C(C=CC3=C4C=C(C=5C=6C(C([C]7C=CC=CC7=5)=O)=CC=C5C4=6)Cl)=C4C3=C5C=C(Cl)C4=C21 KOTVVDDZWMCZBT-UHFFFAOYSA-N 0.000 description 1
- 238000001429 visible spectrum Methods 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
- G03G5/043—Photoconductive layers characterised by having two or more layers or characterised by their composite structure
- G03G5/047—Photoconductive layers characterised by having two or more layers or characterised by their composite structure characterised by the charge-generation layers or charge transport layers
-
- 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
- G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
- G03G5/0614—Amines
- G03G5/06142—Amines arylamine
- G03G5/06144—Amines arylamine diamine
- G03G5/061443—Amines arylamine diamine benzidine
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Light Receiving Elements (AREA)
- Solid State Image Pick-Up Elements (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71640376A | 1976-08-23 | 1976-08-23 | |
| US716,403 | 1976-08-23 | ||
| US79381977A | 1977-05-04 | 1977-05-04 | |
| US793,819 | 1977-05-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1104866A true CA1104866A (en) | 1981-07-14 |
Family
ID=27109525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA281,674A Expired CA1104866A (en) | 1976-08-23 | 1977-06-29 | Imaging member containing a substituted n,n,n',n',- tetraphenyl-[1,1'-biphenyl]-4,4'-diamine in the chargge transport layer |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS599049B2 (enExample) |
| BR (1) | BR7705593A (enExample) |
| CA (1) | CA1104866A (enExample) |
| DE (1) | DE2734990C2 (enExample) |
| FR (1) | FR2363134A1 (enExample) |
| GB (1) | GB1577237A (enExample) |
| MX (2) | MX148708A (enExample) |
| NL (1) | NL186474C (enExample) |
| SU (1) | SU1378794A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8268457B2 (en) | 2006-06-05 | 2012-09-18 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device and material for organic electroluminescent device |
Families Citing this family (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4233383A (en) * | 1979-05-29 | 1980-11-11 | Xerox Corporation | Trigonal selenium photoconductive element |
| US4232103A (en) * | 1979-08-27 | 1980-11-04 | Xerox Corporation | Phenyl benzotriazole stabilized photosensitive device |
| US4410616A (en) * | 1982-05-10 | 1983-10-18 | Xerox Corporation | Multi-layered ambipolar photoresponsive devices for electrophotography |
| US4415639A (en) * | 1982-09-07 | 1983-11-15 | Xerox Corporation | Multilayered photoresponsive device for electrophotography |
| US4582772A (en) * | 1983-02-15 | 1986-04-15 | Xerox Corporation | Layered photoconductive imaging devices |
| CA1231971A (en) * | 1983-10-14 | 1988-01-26 | Trevor I. Martin | Process for preparing aryl amines |
| JPS6097360A (ja) * | 1983-11-01 | 1985-05-31 | Canon Inc | 電子写真感光体 |
| US4725518A (en) * | 1984-05-15 | 1988-02-16 | Xerox Corporation | Electrophotographic imaging system comprising charge transporting aromatic amine compound and protonic acid or Lewis acid |
| US4618551A (en) * | 1985-01-25 | 1986-10-21 | Xerox Corporation | Photoresponsive imaging members with polysilylenes hole transporting compositions |
| JPH0721644B2 (ja) * | 1985-05-31 | 1995-03-08 | 富士ゼロックス株式会社 | 光導電部材 |
| JPS63170647A (ja) * | 1987-01-09 | 1988-07-14 | Fuji Xerox Co Ltd | 電子写真感光体 |
| JP2526969B2 (ja) * | 1988-02-10 | 1996-08-21 | 富士ゼロックス株式会社 | 電子写真用感光体 |
| JPH01153341U (enExample) * | 1988-04-14 | 1989-10-23 | ||
| US5130603A (en) | 1989-03-20 | 1992-07-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
| US5275898A (en) * | 1989-06-06 | 1994-01-04 | Fuji Electric Co., Ltd. | Bisazo photoconductor for electrophotography |
| US4988595A (en) * | 1989-12-18 | 1991-01-29 | Xerox Corporation | Charge transport layer containing different aromatic diamine active charge transport compounds |
| US5187310A (en) * | 1990-03-14 | 1993-02-16 | Kao Corporation | Organic silicon compound, method of its production, and photoreceptor for electrophotography incorporating it |
| US5278014A (en) * | 1991-06-21 | 1994-01-11 | Konica Corporation | Electrophotographic photoreceptor |
| JPH05224439A (ja) * | 1992-02-12 | 1993-09-03 | Fuji Electric Co Ltd | 電子写真用感光体 |
| US5242774A (en) * | 1992-03-27 | 1993-09-07 | Xerox Corporation | Photoconductive imaging members with fluorinated polycarbonates |
| US5306586A (en) * | 1992-08-06 | 1994-04-26 | Xerox Corporation | Dual layer switch photoreceptor structures for digital imaging |
| CA2122328C (en) * | 1993-04-28 | 1999-01-19 | Hideyuki Murata | Thin-film electroluminescent device |
| US6143433A (en) * | 1994-09-14 | 2000-11-07 | Mitsui Chemicals, Inc. | Organic electroluminescent device and process for producing the same |
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Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1314030A (fr) * | 1960-12-08 | 1963-01-04 | Warren S D Co | Feuille de copie électro-photographique et ses applications |
| BE626527A (enExample) * | 1961-12-29 | |||
| US3443937A (en) * | 1965-04-20 | 1969-05-13 | Xerox Corp | Image resolution |
| JPS494339B1 (enExample) * | 1970-06-10 | 1974-01-31 | ||
| DE2108938C2 (de) * | 1971-02-25 | 1984-10-25 | Xerox Corp., Rochester, N.Y. | Elektrofotografisches Aufzeichnungsmaterial und elektrofotografisches Verfahren zur Herstellung eines Ladungsbildes |
| FR2127346A5 (en) * | 1971-02-25 | 1972-10-13 | Xerox Corp | Xerographic plates |
| BE790689A (fr) * | 1971-10-27 | 1973-04-27 | Xerox Corp | Element photosensible comprenant des polymeres photoactifs a quartet exocyclique induit |
| DE2356370C2 (de) * | 1973-11-12 | 1983-05-11 | Hoechst Ag, 6230 Frankfurt | Elektrophotographisches Aufzeichnungsmaterial |
| CA1098755A (en) * | 1976-04-02 | 1981-04-07 | Milan Stolka | Imaging member with n,n'-diphenyl-n,n'-bis (phenylmethyl)-¬1,1'-biphenyl|-4,4'-diamine in the charge transport layer |
-
1977
- 1977-06-29 CA CA281,674A patent/CA1104866A/en not_active Expired
- 1977-07-21 MX MX169936A patent/MX148708A/es unknown
- 1977-07-21 MX MX194207A patent/MX171443B/es unknown
- 1977-08-03 DE DE2734990A patent/DE2734990C2/de not_active Expired
- 1977-08-16 JP JP52098181A patent/JPS599049B2/ja not_active Expired
- 1977-08-18 GB GB34705/77A patent/GB1577237A/en not_active Expired
- 1977-08-22 FR FR7725593A patent/FR2363134A1/fr active Granted
- 1977-08-22 SU SU772517594A patent/SU1378794A3/ru active
- 1977-08-22 BR BR7705593A patent/BR7705593A/pt unknown
- 1977-08-23 NL NLAANVRAGE7709279,A patent/NL186474C/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8268457B2 (en) | 2006-06-05 | 2012-09-18 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device and material for organic electroluminescent device |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2734990C2 (de) | 1986-12-11 |
| MX148708A (es) | 1983-06-06 |
| NL7709279A (nl) | 1978-02-27 |
| JPS5327033A (en) | 1978-03-13 |
| NL186474C (nl) | 1990-12-03 |
| DE2734990A1 (de) | 1978-03-09 |
| FR2363134B1 (enExample) | 1982-06-04 |
| MX171443B (es) | 1993-10-26 |
| FR2363134A1 (fr) | 1978-03-24 |
| GB1577237A (en) | 1980-10-22 |
| BR7705593A (pt) | 1978-06-06 |
| JPS599049B2 (ja) | 1984-02-29 |
| SU1378794A3 (ru) | 1988-02-28 |
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