CN1156850A - 硅类型电荷传送物质的生产方法 - Google Patents
硅类型电荷传送物质的生产方法 Download PDFInfo
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- CN1156850A CN1156850A CN96121687A CN96121687A CN1156850A CN 1156850 A CN1156850 A CN 1156850A CN 96121687 A CN96121687 A CN 96121687A CN 96121687 A CN96121687 A CN 96121687A CN 1156850 A CN1156850 A CN 1156850A
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- Prior art keywords
- silicon
- charge transporting
- ionization potential
- transporting material
- compound
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 36
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- -1 polysiloxane Polymers 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 10
- 125000000962 organic group Chemical group 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 28
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052710 silicon Inorganic materials 0.000 claims description 16
- 229920002554 vinyl polymer Polymers 0.000 claims description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- 230000005012 migration Effects 0.000 claims description 12
- 238000013508 migration Methods 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000010703 silicon Substances 0.000 claims description 6
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 4
- 229910000077 silane Inorganic materials 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- WYROLENTHWJFLR-ACLDMZEESA-N queuine Chemical compound C1=2C(=O)NC(N)=NC=2NC=C1CN[C@H]1C=C[C@H](O)[C@@H]1O WYROLENTHWJFLR-ACLDMZEESA-N 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 34
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- 125000004432 carbon atom Chemical group C* 0.000 abstract description 7
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- 125000005370 alkoxysilyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- 238000007254 oxidation reaction Methods 0.000 description 31
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
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- 238000003756 stirring Methods 0.000 description 20
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- 238000006243 chemical reaction Methods 0.000 description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 239000010410 layer Substances 0.000 description 12
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- 239000011541 reaction mixture Substances 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 10
- 235000005979 Citrus limon Nutrition 0.000 description 9
- 244000248349 Citrus limon Species 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 230000002194 synthesizing effect Effects 0.000 description 9
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- 150000001412 amines Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 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 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 108091029845 Aminoallyl nucleotide Proteins 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229930015698 phenylpropene Natural products 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 3
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 3
- BGGDZDRRHQTSPV-UHFFFAOYSA-N 4-ethenyl-n,n-diphenylaniline Chemical compound C1=CC(C=C)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 BGGDZDRRHQTSPV-UHFFFAOYSA-N 0.000 description 3
- IULUNTXBHHKFFR-UHFFFAOYSA-N 4-methyl-n,n-diphenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 IULUNTXBHHKFFR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000011941 Tilia x europaea Nutrition 0.000 description 3
- 239000007767 bonding agent Substances 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
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- 239000011259 mixed solution Substances 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- BZCGWAXQDLXLQM-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O.ClP(Cl)(Cl)=O BZCGWAXQDLXLQM-UHFFFAOYSA-N 0.000 description 3
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- 229960001866 silicon dioxide Drugs 0.000 description 3
- VBSUMMHIJNZMRM-UHFFFAOYSA-N triethoxy(2-phenylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=CC=C1 VBSUMMHIJNZMRM-UHFFFAOYSA-N 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical class BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000007239 Wittig reaction Methods 0.000 description 2
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- 239000007864 aqueous solution Substances 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000000586 desensitisation Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
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- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000022244 formylation Effects 0.000 description 2
- 238000006170 formylation reaction Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 2
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- 230000009467 reduction Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- BKTWCYHMBXXJBX-UHFFFAOYSA-N 2-ethenyl-n,n-diphenylaniline Chemical compound C=CC1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 BKTWCYHMBXXJBX-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 description 1
- CSFRCLYFVINMBZ-UHFFFAOYSA-N 4-iodo-1,2-dimethylbenzene Chemical class CC1=CC=C(I)C=C1C CSFRCLYFVINMBZ-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
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- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
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- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
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- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
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- 229920001971 elastomer Polymers 0.000 description 1
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- 239000012259 ether extract Substances 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- VVGCMMUYQZSGIX-UHFFFAOYSA-N n,n-diphenyl-2-(2-triethoxysilylethyl)aniline Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 VVGCMMUYQZSGIX-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PKELYQZIUROQSI-UHFFFAOYSA-N phosphane;platinum Chemical compound P.[Pt] PKELYQZIUROQSI-UHFFFAOYSA-N 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 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
- G03G5/08—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being inorganic
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/062—Acyclic or carbocyclic compounds containing non-metal elements other than hydrogen, halogen, oxygen or nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
-
- 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
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Abstract
本发明揭示了一种生产能够将电荷迁移性质传给聚硅氧烷树脂的溶剂可溶的电荷迁移物质的方法。这些物质具有式A-[R1SiR2 3-nQn]p,其中A是叔胺和由具有电荷迁移性质和电离势在4.5-6.2eV范围的化合物衍生得到的有机基团;R1是具有1-18个碳原子的亚烷基;R2是具有1-15个碳原子的单价烃基或卤素-取代的单价烃基;Q是可水解基团如-OR3,其中R3是1-6个碳原子的烷基;和n或p分别是1-3;该硅型电荷迁移物质是具有多个芳基和通过烃基引入到芳环上的烷氧基甲硅烷基的芳族取代的叔胺。
Description
本发明涉及用于电照相有机光电导体的新的电荷迁移物质。
利用有机光导电性物质的电照相有机光电导体由于其生产率,方便的材料设计,和安全性方面的原因正在吸引着人们的注意。它们经历了各种改进并被广泛使用。近几年来,称为功能分离型的结构已经被提出和应用,在该结构中产生电荷层与迁移电荷层分离。具有该结构的电照相有机光电导体有两层。一层由产生电荷的物质和适当的树脂作粘合剂组成。上面的另一层是分散或溶于粘合剂中的电荷迁移物质。含电荷迁移物质的层经常含有电荷迁移材料,和热塑性树脂粘合剂如聚碳酸酯,聚酯,聚丙烯酸酯,和聚苯乙烯;或热固性树脂粘合剂如聚氨酯或环氧树脂。在后面这种情况中,需要通过电晕放电装置将负电荷施加到电荷产生层的表面。但是,该过程产生臭氧,其引起树脂降解,降低灵敏度,和降低树脂的静电充电能力。这导致在后续显影过程中的机械损坏,在纸上的图象转印,和清洗过程中产生的摩擦。由这些因素造成的有机光电导体特性的降低是长期存在的问题。
人们进行过各种研究以解决这些问题。例如,人们进行过各种尝试以便将聚硅氧烷树脂与共聚物成分或另一树脂掺合,如使用热固性聚硅氧烷树脂作为电荷迁移层,JP-A61-238060;使用含有聚硅氧烷树脂的保护层,JP-A62-108260;使用其中已经分散有硅胶,聚氨酯树脂,和/或氟树脂的热固性聚硅氧烷树脂保护层,JP-A4-346356;和使用其中已分散热固性聚硅氧烷树脂的树脂作为保护层或作为电荷迁移材料粘合剂树脂,JP-A4-273252。人们还进行研究以便通过利用聚硅氧烷的性质改善有机光电导体的性能,延长其寿命,和改善其清洗性质。
聚硅氧烷树脂具有特性如透明性,能够经得住介电击穿,光稳定性,和低表面张力,而其他树脂没有这些性质。但由于它们不能与有机化合物配伍,它们不能单独用作构成电荷迁移材料的树脂。相反地,聚硅氧烷树脂被用于通过共聚或掺合改善制造电荷迁移材料的树脂的质量。聚硅氧烷树脂被单独用作制造电荷迁移层的粘合剂时,则必需将电荷迁移物质也溶于聚硅氧烷树脂中。
因此,本发明的目的是提供一种生产这样一种电荷迁移物质的方法,该物质均匀地溶于聚硅氧烷树脂中,它将电荷迁移性质给予用于电照相有机光电导体的树脂。
本发明提供了一种生产硅型电荷迁移物质的方法,其用式(I)A-[R1SiR2 3-nQn]p表示,其中A是芳族取代的叔胺,其具有多个芳基,A是由具有电荷迁移性质和电离势在4.5-6.2eV范围的化合物衍生得到的有机基团;R1是具有1-18个碳原子的亚烷基;R2是具有1-15个碳原子的单价烃基或卤素-取代的单价烃基;Q是可水解基团;n和p分别是1-3的整数。本发明硅型电荷迁移物质的特征在于它表示芳族取代的叔胺,其具有多个芳基,可水解的甲硅烷基,和其中甲硅烷基通过烃基被引入到具有电荷迁移性质和电离势为4.5-6.2eV的化合物的至少一个芳基的芳环上。
可水解基团Q的实例包括羟基,甲氧基,乙氧基,丁氧基,甲基乙基酮肟基,二乙氨基,乙酰氧基,丙烯氧基,和Cl。其中,羟基和烷氧基,尤其是具有1-6个碳原子的烷氧基是优选的。
本发明硅型电荷迁移化合物具有4.5-6.2eV的电离势。当电离势低于4.5eV时,硅型电荷迁移物质容易被氧化和受损使其不符合要求。当电离势超过6.2eV时,从电荷产生层的电荷发射受阻,导致降低灵敏度,也使其不符合要求。本发明的电离势通过室外光电光谱测定法使用由RikenkeikiTM公司生产的表面分析仪AC-1测量。
在本发明提供的硅型电荷迁移物质中,有机硅基团通过烃基与给电子体基团键合。如果它不用烃基直接键合,在电荷迁移物质中的芳基的p电子通过与硅的d电子的p-d相互作用受影响;这样改变了基材的电离势。通过烃基的键合避免了该现象并且便于设计我们的有机光电导体。
在芳环和硅原子之间引入烃基的一种方法 是将不饱和脂族基团与至少在电荷迁移化合物中的多个芳环之一使用硅原子的实质上的取代基是氢原子或烷氧基的烷氧基硅烷通过氢化硅烷化反应键合。例如,通过在与电离势为4.5-6.2eV的芳族取代的叔胺的氮原子键合的芳环上取代的乙烯基与具有与硅键合的氢原子的有机硅化合物之间的氢化硅烷化反应生产硅型电荷迁移物质。将乙烯基引入芳基的一种方法是首先将芳环上的氢原子或甲基甲酰化,最后通过Wittig反应将得到的醛基转化成乙烯基。在该过程之后可以采用氢化硅烷化反应。另一方法是将在芳环上取代的饱和烃基如甲基溴甲基化,然后生产锂-配合物,然后将其与卤代烷氧基硅烷反应。
本发明的电离势为4.5-6.2eV的芳族取代的叔胺A可以选定任何下列化合物(1-18组)。18组化合物中的每一组包括在一页上,总共72个化合物。在这些结构式和下文中,Me是甲基,Et是乙基,Ph是苯基,Bu是丁基,和Pr是丙基。
下面是前面所列的总共72个化合物中的某些(51)芳族取代的叔胺(A)的代表性的氧化和电离势。这些氧化和电离势仅仅对应指的是那些在上面用参考数字,如1A定义的具体化合物。1A-电离势: 5.7eV1B-氧化势: 0.78V电离势: 5.42eV1C-氧化势: 0.81V电离势: 5.45eV3A-氧化势: 0.84V电离势: 5.47eV5A-氧化势: 0.57V电离势: 5.22eV5B-氧化势: 0.75V电离势: 5.40eV5C-氧化势: 0.76V电离势: 5.40eV5D-氧化势: 0.86V电离势: 5.49eV6A-氧化势: 0.76V电离势: 5.40eV6B-氧化势: 0.79V电离势: 5.43eV6C-氧化势: 0.75V电离势: 5.40eV6D-氧化势: 0.77V电离势: 5.41eV7A-氧化势: 0.80V电离势: 5.44eV7B-氧化势: 0.79V 电离势: 5.43eV7C-氧化势: 0.88V电离势: 5.51eV8A-氧化势: 0.76V电离势: 5.40eV8B-氧化势: 0.74V电离势: 5.38eV8C-氧化势: 0.77V电离势: 5.41eV9A-氧化势: 0.63V电离势: 5.28eV9B-氧化势: 0.62V电离势: 5.27eV9C-氧化势: 0.58V电离势: 5.22eV9D-氧化势: 0.59V电离势: 5.23eV10A-氧化势: 0.80V
电离势: 5.44eV10B-氧化势: 0.78V
电离势: 5.43eV10C-氧化势: 0.78V
电离势: 5.43eV10D-氧化势: 0.76V
电离势: 5.41eV11A-氧化势: 0.58V
电离势: 5.23eV11B-氧化势: 0.58V
电离势: 5.23eV11C-氧化势: 0.63V
电离势: 5.28eV11D-氧化势: 0.77V
电离势: 5.41eV12A-氧化势: 0.83V
电离势: 5.47eV12B-氧化势: 0.83V
电离势: 5.47eV12C-氧化势: 0.84V
电离势: 5.47eV12D-氧化势: 0.83V
电离势: 5.47eV13A-氧化势: 0.83V
电离势: 5.47eV13B-氧化势: 0.85V
电离势: 5.48eV13C-氧化势: 0.74V
电离势: 5.38eV13D-氧化势: 0.80V
电离势: 5.44eV14A-氧化势: 0.83V
电离势: 5.47eV14B-氧化势: 0.84V
电离势: 5.47eV14C-氧化势: 0.72V
电离势: 5.36eV14D-氧化势: 0.73V
电离势: 5.38eV14E-氧化势: 0.81V
电离势: 5.45eV17A-氧化势: 0.78V
电离势: 5.43eV17B-氧化势: 0.76V
电离势: 5.40eV17C-氧化势: 0.82V
电离势: 5.46eV17D-氧化势: 0.82V
电离势: 5.45eV18A-氧化势: 0.89V
电离势: 5.52eV18B-氧化势: 0.81V
电离势: 5.45eV18C-氧化势: 0.84V
电离势: 5.47eV18D-氧化势: 0.79V
电离势: 5.43eV
烷氧基硅烷在叔胺的芳环上被引入的位置没有限制,烷氧基硅烷基也不需要与所有芳环键合。确定这些情况通过考虑某些因素如在聚硅氧烷树脂中的溶解性进行。在这种情况下,将乙烯基引入与氮原子键合的芳环的方法是将芳环上取代的氢原子或甲基甲酰化,最后通过Wittig反应将醛基转化成乙烯基。它也可通过在仲胺上的氢与被乙烯基取代的卤代芳基化合物之间的脱去卤化氢的方法来制备。
能够与具有电离势为4.5-6.2eV的叔胺A的芳环键合的乙烯基反应的氢化有机硅化合物是在分子中硅原子上的取代基或者是氢原子或者是烷氧基的氢化有机硅化合物。该化合物通过氢化硅烷化反应加到乙烯基上。直接与硅原子键连的氢原子是加到乙烯基上的氢化硅烷化反应的必要成分。另一必要成分是可水解基团,如烷氧基-OR3。烷氧基的R3是较短的链的基团,即,具有1-6个碳原子的基团,如甲基,乙基,丙基,丁基,戊基和己基或,R3是支链烷基。R3的选择取决于产物的预期用途,氢化硅烷化过程中的稳定性,和所需的可水解性质。
式(I)中的整数n表示在硅上取代的烷氧基的数目。当n大于1时,化合物的亲水性得到改善。当有数个缩合的基团时,该化合物也用作交联剂;所以做出这种选择必须要考虑交联所产生的树脂的硬度,以及其亲水性。
有机基团R2不是氢原子或烷氧基,其直接与硅原子键连,其根据在聚硅氧烷树脂中的硅原子上的取代基的类型,和根据各种性质如在树脂中的溶解性,氢化硅烷化反应的反应活性,和聚硅氧烷树脂的其他性质调整来选择。R2是烷基如甲基,乙基,丙基,丁基,戊基和己基;链烯基如乙烯基或烯丙基;卤代烃基;芳基如苯基或甲苯基;卤代烃基如氯甲基,氯乙基和氯丙基;和用三氟丙基,七氟戊基,和九氟己基代表的氟化烃。如果在聚硅氧烷树脂中的硅原子上的取代基是甲基,则如果R2也是甲基时其溶解性更好。
本发明可固化的聚硅氧烷树脂是可溶于有机溶剂的树脂,和主要选定已知为MT树脂,MQ树脂,T树脂,和聚倍半硅氧烷(polysilsesquioxane)的硅型大分子。生产这些树脂的方法是已知的,如在“Silicon-Based Polymer Science”,由John M.Ziegler和F.W.GordonFearon编写,ACS系列224,美国化学会(1990)的第77页描述的方法。
氢化硅烷化反应使用铂催化剂或有机过氧化物催化剂进行。铂催化剂是用于标准氢化硅烷化反应和加成型聚硅氧烷橡胶的铂化合物;氯化铂;氯铂酸;铂-烯烃配合物;铂-膦配合物;铂被载体支持的物质,如铂/碳,铂/硅胶,和铂/大分子。铂催化剂的量是常规使用量。以摩尔比计,铂金属与给电子体基团的链烯基的数量比范围是1/10至1/100000。
氢化硅烷化反应的温度根据使用的铂催化剂的类型,其数量,反应物质组,和反应条件变化。但是,从效率观点上看,温度应该低于铂催化剂的分解温度,即,低于200℃。在使用有机过氧化物催化剂的情况下,唯一的限制是其半衰期在室温之上。有用的有机过氧化物是自由基聚合引发剂如月桂基过氧化物,丁基过氧化物,和苯甲酰基过氧化物。
氢化硅烷化反应的产物被分成两组。在其中一组中,硅原子被加到乙烯基的α位,在另一组中,硅原子被加到乙烯基的β位。该位置取决于反应条件,如乙烯基化合物取代基的类型和使用的催化剂的类型。在本发明中,混合物对在氢化硅烷化过程中的α-加成和β-加成没有不利影响。事实上,有混合物是优选的,因为它避免了往往容易形成聚集体的电子空穴迁移材料的聚集。
实施例14-[2-(三乙氧基甲硅烷基)乙基]三苯基胺的合成和4-(N,N-二苯基氨基)苯甲醛的合成
将101.4克三苯基胺和35.5毫升二甲基甲酰胺(DMF)放入三颈烧瓶中,同时搅拌并在冰水中冷却,将84.4毫升磷酰氯滴入烧瓶。将温度升至95℃,混合物反应5小时。将反应溶液倒入4升温水中并搅拌1小时。然后收集沉淀并在1∶1的乙醇/水混合溶液中洗涤,得到4-(N,N-二苯基氨基)苯甲醛。产量为91.5克(产率是81.0%)。4-乙烯基三苯基胺的合成
将14.6克氢化钠和700毫升1,2-二甲氧基乙烷放入三颈烧瓶中,同时在室温下搅拌,加入130.8克溴化四甲基鏻。加入一滴无水乙醇之后,混合物在70℃反应4小时。然后将100克4-(N,N-二苯基氨基)苯甲醛加入该混合物中。将反应温度升至70℃,混合物反应5小时。过滤反应溶液,将沉淀的乙醚提取液和滤液在水中洗涤。然后,用氯化钙将乙醚溶液脱水,除去乙醚,得到反应混合物。从乙醇将其重结晶,得到针状柠檬黄的乙烯基三苯基胺。产量是83.4克(产率是84.0%)。4-乙烯基三苯基胺的氢化硅烷化
将40毫升甲苯,9.9克(60毫摩尔)三乙氧基硅烷,和0.018毫摩尔三-(四甲基二乙烯基二硅氧烷)二铂(0,即,在分子中铂的氧化数是0)的甲苯溶液加入三颈烧瓶中,同时在室温下搅拌,将8.2克4-乙烯基三苯基胺的20毫升甲苯溶液滴入烧瓶中。滴加完全后,将混合物在70℃搅拌3小时,然后减压除去溶剂。结果得到4-[2-(三乙氧基甲硅烷基)乙基]三苯基胺的柠檬黄油状物。得到的数量是12.1克(产率91.7%)。实施例24-[2-(甲基二乙氧基甲硅烷基)乙基]三苯基胺的合成和4-乙烯基三苯基胺的氢化硅烷化
将40毫升甲苯,8.1克甲基二乙氧基硅烷,和0.018毫摩尔三-(四甲基二乙烯基二硅氧烷)二铂(0)的甲苯溶液加入三颈烧瓶中,同时在室温下搅拌,将8.2克4-乙烯基三苯基胺的20毫升甲苯溶液滴入烧瓶中。滴加完全后,将混合物在70℃搅拌3小时,然后减压除去溶剂。结果得到4-[2-(甲基二乙氧基甲硅烷基)乙基]三苯基胺的柠檬黄油状物。得到的数量是11.2克(产率91.4%)。实施例34,4’,4”-三-[2-(三乙氧基甲硅烷基)乙基]三苯基胺的合成和三-(4-甲酰基苯基)胺的合成
将50.7克三苯基胺和53.3毫升DMF放入三颈烧瓶中,同时搅拌并在冰水中冷却,将126.6毫升磷酰氯滴入烧瓶。滴加完全之后,将混合物溶液在95℃反应5小时,然后倒入5升温水中并搅拌1小时。然后过滤收集沉淀并在1∶1的乙醇/水混合溶液中洗涤,结果得到65.3克三-(4-甲酰基苯基)胺(产率为95.9%)。三-(4-乙烯基苯基)胺的合成
将14.6克氢化钠和700毫升1,2-二甲氧基乙烷放入三颈烧瓶中,同时在室温下搅拌,加入130.8克溴化四甲基鏻。然后将无水乙醇滴入,滴完之后,在70℃进行反应4小时。然后将反应混合物与40.2克三-(4-(甲酰基苯基)胺合并,在70℃继续反应5小时。将反应产物过滤。将滤饼用乙醇提取,在提取液与滤液合并之后,将混合液用水洗涤。用氯化钙将乙醚溶液脱水之后,除去乙醚,得到反应混合物。将该混合物用乙醇重结晶两次。结果得到针状柠檬黄的三-(4-乙烯基苯基)胺。得到的数量是38.4克(产率是97.3%)。三(4-乙烯基苯基)胺的氢化硅烷化
将40毫升甲苯,9.9克(60毫摩尔)三乙氧基硅烷,和0.018毫摩尔三-(四甲基二乙烯基二硅氧烷)二铂(0)的甲苯溶液加入三颈烧瓶中,同时在室温下搅拌,将3.3克(13毫摩尔)三-(4-乙烯基苯基)胺的20毫升甲苯溶液滴入烧瓶中。滴加完全后,将混合物在70℃搅拌3小时,然后减压除去溶剂。结果得到4,4’,4”-[2-(三乙氧基甲硅烷基)乙基]三苯基胺的柠檬黄油状物,得到的数量是7.8克(产率80.6%)。实施例44-[N,N-二-(3,4-二甲基苯基)氨基]-[2-(三乙氧基甲硅烷基)乙基]苯的合成和N,N-二-(3,4-二甲基苯基)氨基苯的合成
将38.5克(166毫摩尔)4-碘代-邻-二甲苯,22.9克(166毫摩尔)无水碳酸钾,和7.0克铜粉加入20毫升硝基苯中,加热回流8小时并搅拌。将混合物冷却,过滤,和除去滤液。将得到的反应混合物通过硅胶柱,得到N,N-二-(3,4-二甲基苯基)氨基苯。得到的数量是15.7克(产率69%)。4-[N,N-二-(3,4-二甲基苯基)氨基]苯甲醛的合成
将124.6克4-[N,N-二-(3,4-二甲基苯基)氨基]苯和35.5毫升DMF放入三颈烧瓶中,同时搅拌并在冰水中冷却,将84.4毫升磷酰氯滴入烧瓶。滴加完全之后,将混合物溶液在95℃反应5小时,然后倒入4升温水中并搅拌1小时。收集沉淀并在1∶1的乙醇/水混合溶液中洗涤,得到107.6克4-[N,N-二-(3,4-二甲基苯基)氨基]苯甲醛(产率为79.0%)。4-[N,N-二-(3,4-二甲基苯基)氨基]苯乙烯的合成
将12.1克氢化钠和580毫升1,2-二甲氧基乙烷放入三颈烧瓶中,同时在室温下搅拌,加入108.5克溴化四甲基鏻。在滴入一滴无水乙醇之后,将混合物在70℃反应4小时。向反应混合物中加入100克4-[N,N-二-(3,4-二甲基苯基)氨基]苯甲醛,混合物在70℃反应5小时。将反应溶液过滤,将滤饼的乙醚提取物和滤液在水中洗涤。乙醚溶液用氯化钙脱水。除去乙醚,得到反应混合物。将该混合物用乙醇重结晶两次,得到针状的4-[N,N-二-(3,4-二甲基苯基)氨基]苯乙烯。得到的数量是84.5克(产率是85.0%)。4-[N,N-二-(3,4-二甲基苯基)氨基]苯乙烯的氢化硅烷化
将40毫升甲苯,6.0克三乙氧基硅烷,和0.54毫摩尔三-(四甲基二乙烯基二硅氧烷)二铂(0)的甲苯溶液加入三颈烧瓶中,同时在室温下搅拌,将9.9克4-[N,N-二-(3,4-二甲基苯基)氨基]苯乙烯的20毫升甲苯溶液滴入烧瓶中。滴加完全后,将混合物在70℃搅拌3小时,然后减压除去溶剂,得到4-[N,N-二-(3,4-二甲基苯基)氨基]-[2-(三乙氧基甲硅烷基)乙基]苯的柠檬黄油状物。得到的数量是13.4克(产率90.1%)。实施例54-[N,N-二-(3,4-二甲基苯基)氨基]-[2-(三乙氧基甲硅烷基)乙基]苯的合成和4-[N,N-二-(3,4-二甲基苯基)氨基]苯乙烯的氢化硅烷化
将40毫升甲苯,6.0克(37毫摩尔)三乙氧基硅烷,和0.34毫摩尔二氯-(n-环辛-1,5-二烯)铂放入三颈烧瓶中,同时在室温下搅拌,将9.9克4-[N,N-二-(3,4-二甲基苯基)氨基]苯乙烯的20毫升甲苯溶液滴入烧瓶中。滴加完全后,将混合物在70℃搅拌3小时,然后减压除去溶剂,得到4-[N,N-二-(3,4-二甲基苯基)氨基]-[2-(三乙氧基甲硅烷基)乙基]苯的柠檬黄油状物。得到的数量是14.0克(产率94.2%)。实施例64-[3-(三乙氧基甲硅烷基)丙基]三苯基胺)-(4-溴代三苯基胺)的合成
将8.0克(45毫摩尔)N-溴代琥珀酰亚胺(NBS)和10.0克(41毫摩尔)三苯基胺放入200毫升三颈烧瓶中,然后加入150毫升N,N-二甲基甲酰胺。将混合物在室温下搅拌过夜。除去N,N-二甲基甲酰胺,得到的固体物质用四氯化碳提取。除去四氯化碳,反应混合物用乙醇重结晶两次。结果得到8.2克4-溴代三苯基胺白色固体物质(产率61.7%)。4-N,N-二苯基氨基烯丙基苯的合成
向300毫升四颈烧瓶中加入1.0克(40毫摩尔)金属镁并充入氮气。加入100毫升乙醚,开始搅拌。向搅拌着的混合物中慢慢滴加8.6克(27毫摩尔)4-溴代三苯基胺的30毫升乙醚溶液,滴加数量达到3毫升之后,开始慢慢回流。在回流过程中,继续滴加乙醚溶液。滴完后,再回流1小时。将按照上面描述的方法得到的格氏试剂冷却至室温,并与慢慢滴入的2.1克(27毫摩尔)烯丙基氯的40毫升乙醚溶液合并。加完后,将反应混合物回流2小时,然后冷却。加入50毫升冰水,进行水解。萃取乙醚层,用饱和碳酸氢钠水溶液洗涤一次,用水洗涤二次。产物用无水硫酸钠干燥。干燥后,除去乙醚,得到4.9克4-N,N-二苯基氨基烯丙基苯白色固体物质(产率63.2%)。4-N,N-二苯基氨基烯丙基苯的氢化硅烷化
将40毫升甲苯,6.0克(37毫摩尔)三乙氧基硅烷,和0.54毫摩尔三-(四甲基二乙烯基二硅氧烷)二铂(0)的甲苯溶液放入三颈烧瓶中,同时在室温下搅拌,将9.7克(34毫摩尔)4-[N,N-二苯基氨基烯丙基苯的20毫升甲苯溶液滴入烧瓶中。滴加完全后,将混合物在70℃搅拌3小时,然后减压除去溶剂,得到4-[3-(三乙氧基甲硅烷基)丙基]三苯基胺的柠檬黄油状物。得到的数量是10.7克(产率70.1%)。实施例74-[4-(三乙氧基甲硅烷基)丁基]三苯基胺的合成和4-甲基三苯基胺的合成
将4.5克(27毫摩尔)二苯基胺,11.0克(51毫摩尔)对-碘代甲苯,5.5克(40毫摩尔)无水碳酸钾,和1.1克铜碎片加入30毫升邻-二氯苯中。将混合物加热回流7小时并搅拌。反应完全后,将反应溶液过滤,滤液用3-5%硫代硫酸钠水溶液洗涤,然后用饱和盐水洗涤。用无水硫酸钠干燥有机层之后,除去溶剂。将得到的反应混合物用乙醇重结晶,得到5.7克4-甲基三苯基胺(产率81.4%)。4-溴甲基三苯基胺的合成
将6.9克(39毫摩尔)N-溴代琥珀酰亚胺和9.1克(35毫摩尔)4-甲基三苯基胺放入300毫升三颈烧瓶中,加入100毫升四氯化碳。将混合物搅拌过夜。反应完全后,将反应溶液冷却并过滤。除去溶剂,反应混合物用乙醇重结晶。结果得到10.8克4-溴甲基三苯基胺(产率91.2%)。4-N,N-二苯基氨基苯基-1-丁烯的合成
向200毫升四颈烧瓶中加入1.0克(40毫摩尔)金属镁并充入氮气。加入100毫升乙醚,开始搅拌。向搅拌着的混合物中慢慢滴加9.1克(27毫摩尔)4-溴代甲基三苯基胺的20毫升乙醚溶液,滴加数量达到5毫升之后,开始慢慢回流。在回流过程中,继续滴加乙醚溶液。滴完后,再回流1小时。将按照上面描述的方法得到的格氏试剂冷却至室温,并与慢慢滴入的2.1克(27毫摩尔)烯丙基氯的20毫升乙醚溶液合并。滴完后,将反应混合物回流2小时,然后冷却。加入50毫升冰水,进行水解。萃取乙醚层,用饱和碳酸氢钠水溶液洗涤一次,用水洗涤二次。产物用无水硫酸钠干燥。干燥后,除去乙醚,得到5.5克4-N,N-二苯基氨基苯基-1-丁烯白色固体物质(产率66.7%)。4-N,N-二苯基氨基苯基-1-丁烯的氢化硅烷化
将40毫升甲苯,9.9克(60毫摩尔)三乙氧基硅烷,和0.018毫摩尔三-(四甲基二乙烯基二硅氧烷)二铂(0)的甲苯溶液放入三颈烧瓶中,同时在室温下搅拌,将16.7克(54.7毫摩尔)4-[N,N-二苯基氨基苯基-1-丁烯的20毫升甲苯溶液滴入烧瓶中。滴加完全后,将混合物在70℃搅拌3小时,然后减压除去溶剂,结果得到4-[4-(三乙氧基甲硅烷基)丁基]三苯基胺的柠檬黄油状物。得到的数量是13.9克(产率83.2%)。
由上所述可以看到,本发明提供了一种电子空穴迁移物质,该物质可以使具有良好硬度和耐气候特性的低表面能聚硅氧烷有机光电导性树脂得到实际应用,这一点是无法用常规技术实行的。本发明提供的硅型电子空穴迁移物质不仅可以在电照相方法,如照相复制和激光打印中使用,还可以作为在有机电发光元件的结构中必需的电荷迁移层。
Claims (6)
1.一种生产式A-[R1SiR2 3-nQn]p的硅型电荷迁移物质的方法,其中A是具有多个芳基的芳族取代的叔胺,A是由具有电荷迁移性质和电离势在4.5-6.2eV范围的化合物衍生得到的有机基团;R1是具有1-18个碳原子的亚烷基;R2是具有1-15个碳原子的单价烃基或卤素取代的单价烃基;Q是可水解基团;n和p分别是1-3;
该硅型电荷迁移物质的特征在于其由具有多个芳基,和含有可水解基团Q的甲硅烷基的芳族取代的叔胺表示;
所述方法包括将甲硅烷基通过烃基引入到具有电荷迁移性质和电离势在4.5-6.2eV范围的化合物的至少一个芳基的芳环上。
2.根据权利要求1的方法,其中可水解基Q是烷氧基。
3.根据权利要求2的方法,其中具有电荷迁移性质的化合物的一些或所有芳基具有不饱和烃基形式的取代基,该取代基经过与烷氧基硅烷氢化硅烷化得到式A-[R1SiR2 3-nQn]p的硅型电荷迁移物质。
4.根据权利要求1的方法得到的硅型电荷迁移物质。
5.一种生产式A-[R1SiR2 3-nQn]p的硅型电荷迁移物质的方法,其中A是具有多个芳基的芳族取代的叔胺,A是由具有电荷迁移性质和电离势在4.5-6.2eV范围的化合物衍生得到的有机基团;R1是具有1-18个碳原子的亚烷基;R2是具有1-15个碳原子的单价烃基或卤素-取代的单价烃基;Q是可水解基团;和n和p分别是1-3;
所述方法包括将烃基通过氢化硅烷化引入到在芳环上含有乙烯基取代基的具有电荷迁移性质的化合物的该芳环和具有与硅键连的氢原子的有机硅化合物的硅原子之间。
6.可根据权利要求5的方法得到的硅型电荷迁移物质。
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JP3267519B2 (ja) * | 1995-11-06 | 2002-03-18 | キヤノン株式会社 | 電子写真感光体、該電子写真感光体を有するプロセスカートリッジ及び画像形成装置 |
JP3614222B2 (ja) * | 1995-11-06 | 2005-01-26 | ダウ コーニング アジア株式会社 | ケイ素系正孔輸送材の製造方法 |
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-
1995
- 1995-11-06 JP JP7287634A patent/JPH09127710A/ja active Pending
-
1996
- 1996-11-04 US US08/743,265 patent/US5824443A/en not_active Expired - Lifetime
- 1996-11-04 AU AU70593/96A patent/AU708183B2/en not_active Ceased
- 1996-11-06 CN CN96121687A patent/CN1156850A/zh active Pending
- 1996-11-06 KR KR1019960052205A patent/KR100494208B1/ko not_active IP Right Cessation
- 1996-11-06 EP EP96117733A patent/EP0771806B1/en not_active Expired - Lifetime
- 1996-11-06 DE DE69619464T patent/DE69619464T2/de not_active Expired - Fee Related
- 1996-11-13 TW TW085113885A patent/TW348230B/zh not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102219700A (zh) * | 2011-04-22 | 2011-10-19 | 南京邮电大学 | 一种基于芴苯胺结构的有机光电材料 |
Also Published As
Publication number | Publication date |
---|---|
AU708183B2 (en) | 1999-07-29 |
KR970028879A (ko) | 1997-06-24 |
EP0771806B1 (en) | 2002-02-27 |
EP0771806A1 (en) | 1997-05-07 |
US5824443A (en) | 1998-10-20 |
AU7059396A (en) | 1997-05-15 |
KR100494208B1 (ko) | 2005-11-11 |
DE69619464T2 (de) | 2002-10-17 |
JPH09127710A (ja) | 1997-05-16 |
DE69619464D1 (de) | 2002-04-04 |
TW348230B (en) | 1998-12-21 |
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