JPH0421689A - Novel organosilicon compound, its production and photo-sensitive material for electrophotography produced by using the same - Google Patents
Novel organosilicon compound, its production and photo-sensitive material for electrophotography produced by using the sameInfo
- Publication number
- JPH0421689A JPH0421689A JP2122543A JP12254390A JPH0421689A JP H0421689 A JPH0421689 A JP H0421689A JP 2122543 A JP2122543 A JP 2122543A JP 12254390 A JP12254390 A JP 12254390A JP H0421689 A JPH0421689 A JP H0421689A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- general formula
- novel
- silylmethylated
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000000463 material Substances 0.000 title abstract description 31
- 150000003961 organosilicon compounds Chemical class 0.000 title 1
- -1 silane compound Chemical class 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 8
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 229910000077 silane Inorganic materials 0.000 claims abstract description 4
- 108091008695 photoreceptors Proteins 0.000 claims description 61
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 7
- 229920005668 polycarbonate resin Polymers 0.000 claims description 5
- 239000004431 polycarbonate resin Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005649 substituted arylene group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 30
- 230000035945 sensitivity Effects 0.000 abstract description 16
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 4
- 125000000732 arylene group Chemical group 0.000 abstract description 2
- 238000012546 transfer Methods 0.000 abstract description 2
- 239000007983 Tris buffer Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 abstract 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 20
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- 239000000049 pigment Substances 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 10
- 239000004417 polycarbonate Substances 0.000 description 10
- 229920000515 polycarbonate Polymers 0.000 description 10
- 239000003973 paint Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 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 7
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 125000005259 triarylamine group Chemical group 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910021417 amorphous silicon Inorganic materials 0.000 description 3
- 125000005427 anthranyl group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000004407 iron oxides and hydroxides Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- TXIPVVLKTCCGPA-UHFFFAOYSA-N 2-[3-[2-[[1-(cyclopropanecarbonyl)piperidin-3-yl]amino]pyrimidin-4-yl]-2-quinolin-2-ylimidazol-4-yl]acetonitrile Chemical compound C1(CC1)C(=O)N1CC(CCC1)NC1=NC=CC(=N1)N1C(=NC=C1CC#N)C1=NC2=CC=CC=C2C=C1 TXIPVVLKTCCGPA-UHFFFAOYSA-N 0.000 description 1
- KPRPFTOLWQQUAV-OCVAFRRMSA-N 2-amino-N-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-5-[4-[(1R,5S)-3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-1-yl]phenyl]pyridine-3-carboxamide Chemical compound NC1=C(C(=O)NC23CCC(CC2)(CC3)O)C=C(C=N1)C1=CC=C(C=C1)[C@@]12CN(C[C@H]2C1)C1CCOCC1 KPRPFTOLWQQUAV-OCVAFRRMSA-N 0.000 description 1
- CCFPRBJPROSOHQ-UHFFFAOYSA-N 4-[[methyl-bis[[4-(n-phenylanilino)phenyl]methyl]silyl]methyl]-n,n-diphenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C[Si](CC=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)(C)CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 CCFPRBJPROSOHQ-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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- 239000004418 Lexan Substances 0.000 description 1
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- MRIWRLGWLMRJIW-UHFFFAOYSA-N benzyl(trimethyl)silane Chemical compound C[Si](C)(C)CC1=CC=CC=C1 MRIWRLGWLMRJIW-UHFFFAOYSA-N 0.000 description 1
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- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- VIAPGVLSJAGIPY-UHFFFAOYSA-N n-(trimethylsilylmethyl)aniline Chemical compound C[Si](C)(C)CNC1=CC=CC=C1 VIAPGVLSJAGIPY-UHFFFAOYSA-N 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 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 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- 229920001230 polyarylate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
゛本発明は新規シリルメチル化トリアリールアミン化合
物、その製造方法及び該新規シリルメチル化トリアリー
ルアミン化合物を電荷輸送材として用いた高感度、高耐
久性の電子写真感光体に関するものである。[Detailed Description of the Invention] [Field of Industrial Application] [The present invention relates to a novel silylmethylated triarylamine compound, a method for producing the same, and a highly sensitive and highly durable method using the novel silylmethylated triarylamine compound as a charge transport material. This invention relates to an electrophotographic photoreceptor.
近年、電子写真方式を用いた複写機、プリンターの発展
は目覚ましく、用途に応じて様々な形態、種類、機能の
機種が開発され、それに対応してそれらに用いられる感
光体も多種多様のものが開発されつつある。In recent years, the development of copiers and printers using electrophotography has been remarkable, and models with various shapes, types, and functions have been developed depending on the purpose, and correspondingly, the photoreceptors used in them have also become diverse. It is being developed.
従来、電子写真感光体としては、その感度、耐久性の面
から無機化合物が主として用いられてきた。例えば、酸
化亜鉛、硫化カドミウム、セレン等を挙げることができ
る。しかしながら、これらは有害物質を使用している場
合が多く、その廃棄が問題となり、公害をもたらす原因
となる。又、感度が良好なセレンを用いる場合、蒸着法
等により導電性基体上に薄膜を形成する必要があり、生
産性が劣り、コストアップの原因となる。Conventionally, inorganic compounds have been mainly used as electrophotographic photoreceptors due to their sensitivity and durability. Examples include zinc oxide, cadmium sulfide, and selenium. However, these often use harmful substances, and their disposal becomes a problem and causes pollution. Furthermore, when selenium, which has good sensitivity, is used, it is necessary to form a thin film on a conductive substrate by a vapor deposition method or the like, resulting in poor productivity and increased costs.
近年、無公害性の無機物感光体としてアモルファスシリ
コンが注目され、その研究開発が進められている。しか
しながら、これらも感度については優れているが、薄膜
形成時において、主にプラズマＣＶＤ法を用いるた約、
その生産性は極めて劣っており、感光体コスト、ランニ
ングコストとも大きなものとなっている。In recent years, amorphous silicon has attracted attention as a non-polluting inorganic photoreceptor, and its research and development is progressing. However, although these also have excellent sensitivity, when forming thin films, the plasma CVD method is mainly used.
Its productivity is extremely poor, and both the photoreceptor cost and running cost are large.
一方、有機感光体は、焼却が可能であり、無公害の利点
を有し、更に多くのものは塗工により薄膜形成が可能で
大量生産が容易である。それ故にコストが大幅に低減で
き、又、用途に応じて様々な形状に加工することができ
るという長所を有している。しかしながら、有機感光体
においては、その感度、耐久性に問題が残されており、
高感度、高耐久性の有機感光体の出現が強く望まれてい
る。On the other hand, organic photoreceptors can be incinerated and have the advantage of being non-polluting, and many of them can be coated to form thin films, making mass production easy. Therefore, it has the advantage of being able to significantly reduce costs and being able to be processed into various shapes depending on the application. However, organic photoreceptors still have problems with their sensitivity and durability.
The emergence of organic photoreceptors with high sensitivity and high durability is strongly desired.
有機感光体の感度向上の手段として様々な方法が提案さ
れているが、現在では電荷発生層と電荷輸送層とに機能
が分離した主に二層構造の機能分離型感光体が主流とな
っている。例えば、露光により電荷発生層で発生した電
荷は、電荷輸送層に注入され、電荷輸送層中を通って表
面に輸送され、表面電荷を中和することにより感光体表
面に静電潜像が形成される。機能分離型は単層型に比し
て発生した電荷が捕獲される可能性が小さくなり、各層
がそれぞれの機能を阻害されることなく、効率よく電荷
が感光体表面に輸送され得る（Ｔメリ力特許第２８０３
５４１号）。Various methods have been proposed to improve the sensitivity of organic photoreceptors, but currently the mainstream is a functionally separated photoreceptor with a two-layer structure in which the functions are separated into a charge generation layer and a charge transport layer. There is. For example, charges generated in the charge generation layer due to exposure to light are injected into the charge transport layer, transported through the charge transport layer to the surface, and by neutralizing the surface charges, an electrostatic latent image is formed on the surface of the photoreceptor. be done. Compared to the single-layer type, the function-separated type has a smaller possibility that generated charges will be captured, and the charges can be efficiently transported to the photoreceptor surface without each layer having its own function inhibited (T Merit). Power Patent No. 2803
No. 541).
電荷発生層に用いられる有機電荷発生材としては、照射
される光のエネルギーを吸収し、効率よく電荷を発生す
る化合物が選択使用されており、例えば、アゾ顔料（特
開昭５４−１４９６７号公報）、無金属フタロシアニン
顔料（特開昭６０−１４３３４６号公報）、金属フタロ
シアニン顔料（特開昭５０−１６５３８号公報）、スク
エア １Ｊウム塩（特開昭５３−２７０３３号公報）等
を挙げることができる。As the organic charge generating material used in the charge generating layer, compounds that absorb the energy of irradiated light and efficiently generate charges are selectively used. ), metal-free phthalocyanine pigments (JP-A-60-143346), metal phthalocyanine pigments (JP-A-50-16538), square 1J um salt (JP-A-53-27033), etc. can.
電荷輸送層に用いられる電荷輸送材としては電荷発生層
からの電荷の注入効率が大きく、更に電荷輸送層内での
電荷の移動度が大である化合物を選定する必要がある。As the charge transport material used in the charge transport layer, it is necessary to select a compound that has a high charge injection efficiency from the charge generation layer and also has a high charge mobility within the charge transport layer.
そのためには、イオン化ポテンシャルが小さい化合物、
カチオンラジカルが発生し易い化合物が選ばれ、例えば
、トリアリールアミン誘導体（特開昭５３−４７２６０
号公報）、ヒドラシン誘導体（特開昭５７−１０１８４
４号公報）、オキサジアゾール誘導体（特公昭３４−５
４６６号公報）、ピラゾリン誘導体（特公昭５２−４１
８８号公報）、スチルベン誘導体（特開昭５８−１９８
０４３号公報）、トリフェニルメタン誘導体（特公昭４
５−５５５号公報）、１．３−ブタジェン誘導体（特開
昭６２−２８７２５７号公報）等が提案されている。For this purpose, compounds with small ionization potential,
Compounds that easily generate cation radicals are selected, such as triarylamine derivatives (Japanese Patent Laid-Open No. 53-47260
Publication No.), hydracine derivatives (Japanese Patent Application Laid-Open No. 57-10184
4), oxadiazole derivatives (Japanese Patent Publication No. 34-5)
466), pyrazoline derivatives (Japanese Patent Publication No. 52-41
No. 88), stilbene derivatives (JP-A-58-198)
No. 043), triphenylmethane derivatives (Special Publication No. 4
5-555), 1,3-butadiene derivatives (JP-A-62-287257), etc. have been proposed.
しかしながら、前記の如くこれら有機感光体の電荷移動
度は、無機物感光体に比較すると小さいものであり、感
度の点においてまだまだ満足できるものではない。However, as mentioned above, the charge mobility of these organic photoreceptors is smaller than that of inorganic photoreceptors, and their sensitivity is still unsatisfactory.
また、帯電、露光、現像、転写、除電という一連の電子
写真プロセスにおいて、感光体は極めて過酷な条件下に
おかれ、特にその耐オゾン性、耐摩耗性が大きな問題と
なり、これらの耐久性が要求されているが、満足できる
ものは未だ得られていない。Furthermore, in a series of electrophotographic processes such as charging, exposure, development, transfer, and static elimination, photoreceptors are subjected to extremely harsh conditions, and their ozone resistance and abrasion resistance in particular become major issues, and their durability is a major issue. There are demands for this, but nothing that satisfies them has yet been achieved.
なかでも、トリアリールアミン誘導体については多くの
誘導体の開発が試みられている。例えば、モノトリアリ
ールアミン（特開昭５７−１９５２５４号公報、特開平
１−１１８１４７号公報、特開平１−１１８１４２号公
報）、ビス（ジアリールアミノ）−ベンゼン（特開昭５
５−１４４２５０号公報、特開平１−１１８１４４号公
報、特開平１−１１８１４６号公報）、ビストリアリー
ル−アミン（特開昭５３−２７０３３号公報、特開昭５
６−３５１４０号公報、特開昭５６−５２７５６号公報
、特開平１−１４２６４７号公報）等が挙げられる。Among these, many attempts have been made to develop triarylamine derivatives. For example, monotriarylamine (JP-A-57-195254, JP-A-1-118147, JP-A-1-118142), bis(diarylamino)-benzene (JP-A-57-195254, JP-A-1-118147, JP-A-1-118142),
5-144250, JP-A-1-118144, JP-A-1-118146), bistriaryl-amine (JP-A-53-27033, JP-A-5)
6-35140, JP-A-56-52756, JP-A-1-142647), and the like.
しかしながら、モノトリアリールアミンは一般に合成は
容易であるも、電荷移動度が充分でなく、また、安定性
に欠けるという問題があり、ビス（ジアリールアミノ）
−ベンゼン及びビストリアリールアミンは一般に、電荷
移動度はある程度優れているものの、安定性に欠け、ま
た合成が容易でないという問題がある。また、これらの
トリアリールアミン誘導体はいずれも結着樹脂との相溶
性がないことも問題点として指摘されていた。However, although monotriarylamines are generally easy to synthesize, they have problems such as insufficient charge mobility and lack of stability.
- Benzene and bistriarylamine generally have some degree of excellent charge mobility, but they lack stability and are not easy to synthesize. It has also been pointed out that these triarylamine derivatives are not compatible with the binder resin as a problem.
このように、トリアリールアミン誘導体等の従来の有機
感光体には多くの問題点がみられ、これらを改良するこ
とが当該技術分野で強く要請されているのが実情である
。As described above, conventional organic photoreceptors such as triarylamine derivatives have many problems, and there is a strong demand in the technical field to improve these problems.
本発明の目的は、まさにこの点にあり、かかる課題を解
消するものとして、優れた電荷移動度と安定性を有し、
かつ結着樹脂との相溶性を有する電荷輸送材として有益
な新規化合物を提供することにある。The purpose of the present invention is exactly this point, and as a device that solves this problem, it has excellent charge mobility and stability,
Another object of the present invention is to provide a novel compound useful as a charge transport material that is compatible with a binder resin.
本発明の他の目的は、当該新規化合物の製造方法を提供
することにある。Another object of the present invention is to provide a method for producing the new compound.
本発明のさらに他の目的は、当該新規化合物を電荷輸送
材として用いた高感度、高耐久性の電子写真感光体を提
供することにある。Still another object of the present invention is to provide a highly sensitive and highly durable electrophotographic photoreceptor using the new compound as a charge transport material.
本発明者らは上記課題を解決すべく鋭意研究した結果、
本発明を完成するに至った。As a result of intensive research by the present inventors to solve the above problems,
The present invention has now been completed.
即ち、本発明は、
一般式（Ｉ）で示される新規シリルメチル化トリアリー
ルアミン化合物、
〔以下余白〕
Ａｒ’
い、・／＼。、・
（式中、Ａｒ’は置換されていてもよいアリーレン基を
示し、３つのＡｒ’は同一でも異なっていてもよい。Ａ
ｒ２は置換されていてもよいアリール基を示し、６つの
Ａｒ２は同一でも異なっていてもよい。Ｒ１は置換され
ていてもよいアルキル基、シクロアルキル基、アラルキ
ル基又はアリール基を示す。）に関し、また当該新規シ
リルメチル化トリアリールアミン化合物の製造方法及び
それを用いた電子写真感光体に関する。That is, the present invention provides a novel silylmethylated triarylamine compound represented by the general formula (I), [blank below] Ar' ./\. ,・(In the formula, Ar' represents an optionally substituted arylene group, and the three Ar's may be the same or different.A
r2 represents an optionally substituted aryl group, and six Ar2s may be the same or different. R1 represents an optionally substituted alkyl group, cycloalkyl group, aralkyl group or aryl group. ), and also relates to a method for producing the novel silylmethylated triarylamine compound and an electrophotographic photoreceptor using the same.
前記一般式（Ｉ）において、Ａｒ１で表されるアリーレ
ン基としては、フェニレン、ナフチレン、アンズラニロ
ン等が例示され、好ましくはフェニレン、ナフチレンで
ある。Ａｒ’は置換されていてもよいが、置換基として
は通常、アルキル基が挙げられ、メチル、エチルが例示
される。In the general formula (I), examples of the arylene group represented by Ar1 include phenylene, naphthylene, and anzuranylon, with phenylene and naphthylene being preferred. Ar' may be substituted, and the substituent is usually an alkyl group, exemplified by methyl and ethyl.
Ａ ｒ ２で表されるアリール基としては、フェニル、
ナフチル、アンスラニル等が挙げられ、好ましくはフェ
ニルである。Ａｒ’は置換されていてもよいが、置換基
よしては通常、アルキル基、アルコキシ基等が挙げられ
、アルキル基としては、メチル、エチル、ｎ−プロピル
、イソプロピル、ｎ−ブチル等の炭素数１〜４の直鎮も
しくは分岐のアルキル基が例示され、好ましくはメチル
である。また、アルコキシ基としては、メトキシ、エト
キシ等が例示される。The aryl group represented by A r 2 includes phenyl,
Examples include naphthyl and anthranyl, with phenyl being preferred. Ar' may be substituted, but substituents usually include alkyl groups, alkoxy groups, etc., and examples of alkyl groups include carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, etc. Examples include 1 to 4 straight or branched alkyl groups, preferably methyl. Furthermore, examples of the alkoxy group include methoxy and ethoxy.
Ｒ１はアルキル基、シクロアルキル基、アラルキル基又
はアリール基を表すが、アルキル基としては、炭素数１
〜１０の直鎮もしくは分枝のアルキル基が好ましく、具
体的にはメチル、エチル、ｎ−プロピル、イソプロピル
、ｎ−ブチル、ｎ−ペンチル、ｎ−ヘキシル、ｎ−ヘプ
チル、ｎ−オクチル、ｎ−ノニル、ｎ−デシル等が挙げ
られ、好ましくはメチル、エチル、ｎ−プロピル、イソ
プロピル、ｎ−ブチルである。このアルキル基は置換さ
れていてもよいが、置換基としては通常、アルコキシ基
等が挙げられ、好ましくはメトキシ又はエトキシがよい
。R1 represents an alkyl group, a cycloalkyl group, an aralkyl group, or an aryl group, and the alkyl group has 1 carbon number.
~10 straight or branched alkyl groups are preferred, specifically methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n- Nonyl, n-decyl, etc. are mentioned, and methyl, ethyl, n-propyl, isopropyl, and n-butyl are preferable. This alkyl group may be substituted, and the substituent usually includes an alkoxy group, preferably methoxy or ethoxy.
Ｒ１がシクロアルキル基である場合、無置換もしくはア
ルキル基等で置換された炭素数８以下のシクロアルキル
基が挙げられ、具体的にはシクロプロピル、シクロペン
チル、シクロヘキシル、シクロヘプチル、シクロオクチ
ル等を例示することができ、好ましくはシクロヘキシル
である。When R1 is a cycloalkyl group, examples include unsubstituted or substituted cycloalkyl groups having 8 or less carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc. and preferably cyclohexyl.
Ｒ１がアラルキル基である場合、アリール長部分が無置
換もしくはアルキル基、アルコキシ基等で置換されたフ
ェニル、ナフチル、アンスラニル等が挙げられ、アルキ
レン基部分としては、炭素数１〜４のものが挙げられ、
好ましくはメチレンである。具体的には、ベンジル、ｐ
−メチルベンジル、ｍ−メチルベンジル等が挙げられる
。When R1 is an aralkyl group, examples include phenyl, naphthyl, anthranyl, etc. in which the long aryl portion is unsubstituted or substituted with an alkyl group, an alkoxy group, etc., and examples of the alkylene group include those having 1 to 4 carbon atoms. is,
Preferably it is methylene. Specifically, benzyl, p
-methylbenzyl, m-methylbenzyl and the like.
Ｒ’が了リール基である場合、了リール基が無置換もし
くはアルキル基、アルコキシ基等で置換されたフェニル
、ナフチル、アンスラニル等カ挙げられ、好ましくはフ
ェニルである。When R' is a Ryl group, examples thereof include phenyl, naphthyl, anthranyl, etc., which are unsubstituted or substituted with an alkyl group, an alkoxy group, etc., with phenyl being preferred.
ここで、Ｒ’が炭素数が１０以下のアルキル基の場合に
は常温で固体であり、電子写真感光体用の電荷輸送材と
しては好ましいものである。しかし、炭素数が１１以上
のアルキル基である場合には液体よなり、電子写真感光
体用の電荷輸送材としては好ましくない。Ｒ’がシクロ
アルキル基、アリール基、もしくはアラルキル基の場合
には特に限定されることはなく、いずれも常温で固体に
なるので、問題なく電荷輸送材として使用できる。Here, when R' is an alkyl group having 10 or less carbon atoms, it is solid at room temperature and is preferable as a charge transport material for electrophotographic photoreceptors. However, when it is an alkyl group having 11 or more carbon atoms, it becomes liquid and is not preferred as a charge transport material for electrophotographic photoreceptors. When R' is a cycloalkyl group, an aryl group, or an aralkyl group, there is no particular limitation, and since all of them become solid at room temperature, they can be used as a charge transport material without any problems.
本発明における一般式（Ｉ）で示される新規シリルメチ
ル化トリアリールアミン化合物は、一般式（ｎ）で示さ
れるグリニヤール試薬と３官能性シラン化合物を反応さ
せることによって製造することができる。The novel silylmethylated triarylamine compound represented by general formula (I) in the present invention can be produced by reacting a Grignard reagent represented by general formula (n) with a trifunctional silane compound.
（式中、Ａ ｒ’、 Ａｒ’は式（Ｉ）と同じ意味を
有し、Ｘ４はハロゲン原子を示す。）
一般式（ｎ）において Ｘ ４で表されるノ＼ロゲン原
子としては塩素、臭素、ヨウ素のいずれでもよい。(In the formula, Ar' and Ar' have the same meanings as in formula (I), and X4 represents a halogen atom.) In the general formula (n), the halogen atom represented by X4 is chlorine, Either bromine or iodine may be used.
本発明に用いられる一般式（ｎ）で示されるグリニヤー
ル試薬は、ハロゲノメチル化トリアリールアミン化合物
とマグネシウム金属とを原料にして公知の方法で得るこ
とができる。即ち、エーテル系溶剤中でハロゲノメチル
化トリアリールアミン化合物とマグネシウム金属により
、一般式（■）で示されるグリニヤール試薬を調製する
。ハロゲノメチル化トリアリールアミン化合物は、トリ
アリールアミン化合物を公知の方法でハロゲノメチル化
することにより容易に得ることができる。The Grignard reagent represented by the general formula (n) used in the present invention can be obtained by a known method using a halogenomethylated triarylamine compound and magnesium metal as raw materials. That is, a Grignard reagent represented by the general formula (■) is prepared using a halogenomethylated triarylamine compound and magnesium metal in an ether solvent. A halogenomethylated triarylamine compound can be easily obtained by halogenomethylating a triarylamine compound by a known method.
エーテル系溶剤としては、例えばジエチルエーテル、エ
チレングリコールジメチルエーテル、エチレングリコー
ルジエチルエーテル、ジエチレングリコールジメチルエ
ーテル、ジエチレングリコールジエチルエーテル、テト
ラヒドロフラン、ジオキサン、ジイソプロピルエーテル
、ジ−ｎ−ブチルエーテル等を挙げることができ、好ま
しくはジエチルエーテル、テトラヒドロフランを用いる
のが良い。Examples of ether solvents include diethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, dioxane, diisopropyl ether, di-n-butyl ether, etc., preferably diethyl ether, It is better to use tetrahydrofuran.
このようにして得られたグリニヤール試薬のエーテル系
溶剤溶液に、一般式（Ｉ）
Ｘ’Ｘ”Ｘ３ＳｉＲ’ （ＩＩＩ）
（式中、Ｒ１は式（Ｉ）と同じ意味を有し、ｘｌ。To the thus obtained ethereal solvent solution of the Grignard reagent, the general formula (I) X'X"X3SiR' (III)
(wherein R1 has the same meaning as in formula (I), xl.
ｘ２．ｘ３はハロゲン原子又はアルコキシ基を示す。）
で示される３官能性シラン化合物を、必要に応じて前記
エーテル系溶剤に希釈して滴下する。x2. x3 represents a halogen atom or an alkoxy group. )
A trifunctional silane compound represented by is diluted in the ether solvent as necessary and added dropwise.
ここで、ｘ’ ｘ’、ｘ３がハロゲン原子を表す場合
は、塩素、臭素、ヨウ素のいずれでもよい。Here, when x'x' and x3 represent a halogen atom, they may be any of chlorine, bromine, and iodine.
また、アルコキシ基を表す場合としては、直鎮もしくは
分枝状のいずれでも良く、その炭素数としては１〜４が
好ましく、例えばメトキシ、エトキシ、プロポキシ、イ
ソプロポキシ、ｎ−ブトキシ等が例示される。このよう
にｘ’、ｘ”、ｘ３はハロゲン原子又はアルコキシ基を
示すが反応性の面からハロゲン原子が好ましい。Further, when representing an alkoxy group, it may be straight or branched, and preferably has 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, etc. . In this way, x', x'', and x3 represent a halogen atom or an alkoxy group, and a halogen atom is preferred from the viewpoint of reactivity.
滴下する量としては、通常グリニヤール試薬に対して０
．３倍モル乃至０．５倍モルであり、好ましくは０．３
３倍モルである。滴下時間は通常、３０分間乃至５時間
であるが、好ましくは３０分間乃至２時間である。また
、滴下温度としては、通常５０℃乃至１００℃であるが
、好ましくは一１０℃乃至５０℃であり、必要に応じて
冷却、加温を行なう。The amount to be added is usually 0 to Grignard reagent.
．． 3 times mole to 0.5 times mole, preferably 0.3 times mole
It is 3 times the mole. The dropping time is usually 30 minutes to 5 hours, preferably 30 minutes to 2 hours. Further, the dropping temperature is usually 50°C to 100°C, preferably 110°C to 50°C, and cooling and heating are performed as necessary.
滴下終了後反応を熟成し、その後加水分解を行い常法に
従い処理することにより、一般式（Ｉ）で示される新規
シリルメチル化トリアリールアミン化合物を高収率で得
ることができる。After completion of the dropwise addition, the reaction is aged, followed by hydrolysis and treatment according to a conventional method, whereby a novel silylmethylated triarylamine compound represented by general formula (I) can be obtained in high yield.
以上のようにして得られる一般式（Ｉ）に示されるシリ
ルメチル化トリアリールアミン化合物のうち、特に常温
で固体のものは、シリルメチル基の超共役効果によりカ
チオンラジカルが安定化され、正電荷移動度が大きくな
り、電子写真感光体用の電荷輸送材としては好適である
。シリルメチル化アリール化合物は、従来よりカチオン
ラジカル安定化合物として多く知られているが（例えば
、ジャーナル オブ オルガノメタリック ケミストリ
ー、２９巻、３３頁、１９７１年）、いずれもトリメチ
ルシリルメチルベンゼン、トリメチルシリルメチルアニ
リン等のベンゼン誘導体であり、本発明ではトリアリー
ルアミン誘導体とすることにより、−層カチオンラジカ
ルを安定化させることができ、電荷移動度を更に大きく
することが可能となった。Among the silylmethylated triarylamine compounds represented by the general formula (I) obtained as described above, those that are solid at room temperature in particular stabilize cation radicals due to the hyperconjugation effect of the silylmethyl group, and have a high positive charge mobility. is large, making it suitable as a charge transport material for electrophotographic photoreceptors. Silylmethylated aryl compounds have long been known as cation radical-stabilizing compounds (for example, Journal of Organometallic Chemistry, Vol. 29, p. 33, 1971), but they all contain benzenes such as trimethylsilylmethylbenzene and trimethylsilylmethylaniline. In the present invention, by using a triarylamine derivative, the -layer cation radical can be stabilized, and the charge mobility can be further increased.
又、これらの化合物は電子写真プロセスにおいて発生す
るオゾン酸化に対しても安定であり、高感度、高耐久性
の電子写真感光体を与えるものである。Furthermore, these compounds are stable against ozone oxidation generated in the electrophotographic process, and provide electrophotographic photoreceptors with high sensitivity and high durability.
以下、一般式（Ｉ）で示される新規シリルメチル化トリ
アリールアミン化合物を具体的に例示するが（化合物（
１）〜（３２） ） 、本発明はこれらに限定されるも
のではない。Hereinafter, the novel silylmethylated triarylamine compound represented by the general formula (I) will be specifically exemplified (compound (
1) to (32)), but the present invention is not limited thereto.
１１、Ｃ ＣＨ。 11.C CH.
これらの化合物は、多くの溶剤に可溶であり、例えば、
ベンゼン、トルエン、キシレン、テトラリン、クロロベ
ンゼン等の芳香族系溶剤；ジクロロメタン、クロロホル
ム、トリクロロエチレン、テトラクロロエチレン、四塩
化炭素等のハロゲン系溶剤；酢酸メチル、酢酸エチル、
酢酸プロピル、ギ酸メチル、ギ酸エチル等のエステル系
溶剤；アセトン、メチルエチルケトン等のケトン系溶剤
；ジエチルエーテル、ジプロピルエーテル、ジオキサン
、テトラヒドロフラン等のエーテル系溶剤；メタノール
、エタノール、イソプロピルアルコール等のアルコール
系溶剤；ジメチルホルムアミド、ジメチルアセトアミド
、ジメチルスルホキシド等に可溶である。These compounds are soluble in many solvents, e.g.
Aromatic solvents such as benzene, toluene, xylene, tetralin, chlorobenzene; halogen solvents such as dichloromethane, chloroform, trichloroethylene, tetrachloroethylene, carbon tetrachloride; methyl acetate, ethyl acetate,
Ester solvents such as propyl acetate, methyl formate, and ethyl formate; Ketone solvents such as acetone and methyl ethyl ketone; Ether solvents such as diethyl ether, dipropyl ether, dioxane, and tetrahydrofuran; Alcohol solvents such as methanol, ethanol, and isopropyl alcohol ;Soluble in dimethylformamide, dimethylacetamide, dimethylsulfoxide, etc.
電子写真感光体を作製するにあたっては、例えば、導電
性支持体上に電荷発生層及び電荷輸送層を薄膜上に形成
せしめる。導電性支持体の基材としては、アルミニウム
、ニッケル等の金属、金属蒸着高分子フィルム、金属ラ
ミネート高分子フィルム等を用いることができ、ドラム
状、シート状又はベルト状の形態で導電性支持体を形成
する。In producing an electrophotographic photoreceptor, for example, a charge generation layer and a charge transport layer are formed as thin films on a conductive support. As the base material of the conductive support, metals such as aluminum and nickel, metal-deposited polymer films, metal-laminated polymer films, etc. can be used, and the conductive support is formed in the form of a drum, sheet, or belt. form.
電荷発生層は、電荷発生材及び必要に応じて結合剤、添
加剤よりなり、蒸着法、プラズマＣＶＤ法、塗工法等の
方法で作製することができる。The charge generation layer is made of a charge generation material and, if necessary, a binder and additives, and can be produced by a method such as a vapor deposition method, a plasma CVD method, or a coating method.
電荷発生材としては、特に限定されることはなく照射さ
れる特定の波長の光を吸収し、効率よく電荷を発生し得
るものなら有機材料、無機材料のいずれも好適に使用す
ることができるが、無機材料の場合は前記の如く、公害
の問題や経済性に問題があるため、かかる観点において
有機材料を用いることが好ましい。The charge generating material is not particularly limited, and any organic or inorganic material can be suitably used as long as it absorbs irradiated light of a specific wavelength and can efficiently generate charges. In the case of inorganic materials, as mentioned above, there are problems with pollution and economic efficiency, so from this point of view it is preferable to use organic materials.
有機電荷発生材としては、例えば、ペリレン顔料、多環
キノン系顔料、無金属フタロシアニン顔料、金属フタロ
シアニン顔料、ビスアソ顔料、トリスアゾ顔料、チアピ
リリウム塩、スクェアリウム塩、アズレニウム顔料等が
挙げられ、これらは主として結合剤中に分散せしめ、塗
工により電荷発生層を形成することができる。無機電荷
発生材としては、セレン、セレン合金、硫化カドミウム
、酸化亜鉛、アモルファスシリコン、アモルファスシリ
コンカーバイド等が挙げられる。なかでも半導体レーザ
ー波長域では、特にＸ型無金属フタロシアニン顔料が、
可視光領域ではジブロモアントアントロン顔料がその感
度の点において最も優れている。Examples of organic charge-generating materials include perylene pigments, polycyclic quinone pigments, metal-free phthalocyanine pigments, metal phthalocyanine pigments, bisaso pigments, trisazo pigments, thiapyrylium salts, squareium salts, and azulenium pigments. A charge generation layer can be formed by dispersing it in a binder and coating it. Examples of the inorganic charge generating material include selenium, selenium alloy, cadmium sulfide, zinc oxide, amorphous silicon, amorphous silicon carbide, and the like. Among them, in the semiconductor laser wavelength range, X-type metal-free phthalocyanine pigments are particularly effective.
In the visible light region, dibromoanthanthrone pigments are the most superior in terms of sensitivity.
形成された電荷発生層の膜厚は、０．１乃至２．０μｍ
が好ましく、更に好ましくは０．１乃至１．０μｍであ
る。The thickness of the formed charge generation layer is 0.1 to 2.0 μm.
is preferable, and more preferably 0.1 to 1.0 μm.
次に該電荷発生層の上部に、一般式（Ｉ）で示される新
規シリルメチル化トリアリールアミン化合物を含む電荷
輸送層を薄膜状に形成せしめる。Next, a charge transport layer containing a novel silylmethylated triarylamine compound represented by the general formula (I) is formed in the form of a thin film on top of the charge generation layer.
薄膜形成法としては、おもに塗工法が用いられ、一般式
（Ｉ）で示される新規シリルメチル化トリアリールアミ
ン化合物を、必要に応じて結合剤とともに溶剤に溶解し
、電荷発生層上に塗工せしめ、その後乾燥させればよい
。A coating method is mainly used to form a thin film, in which a novel silylmethylated triarylamine compound represented by general formula (I) is dissolved in a solvent together with a binder if necessary, and coated on the charge generation layer. , then dry it.
用いられる溶剤としては、上記の化合物及び必要に応じ
て用いられる結合剤が溶解し、かつ電荷発生層が溶解し
ない溶剤なら特に限定されることはない。The solvent to be used is not particularly limited as long as it dissolves the above-mentioned compound and the binder used if necessary, but does not dissolve the charge generation layer.
必要に応じて用いられる結合剤は、絶縁性樹脂なら特に
限定されることはなく、例えば、ポリカーボネート、ボ
リアリレート、ポリエステル、ポリアミド等の縮合系重
合体；ポリエチレン、ポリスチレン、スチレン−アクリ
ル共重合体、ポリアクリレート、ポリメタクリレート、
ポリビニルブチラール、ポリアクリロニトリル、ポリア
クリル了ミド、アクリロニトリル−ブタジェン共重合体
、ポリ塩化ビニル、塩化ビニル−酢酸ビニル共重合体、
等の付加重合体；ポリスルホン、ポリエーテルスルホン
、シリコン樹脂等が適宜用いられ、種もしくは二種以上
のものを混合して用いることができる。The binder used as necessary is not particularly limited as long as it is an insulating resin, and examples thereof include condensation polymers such as polycarbonate, polyarylate, polyester, and polyamide; polyethylene, polystyrene, styrene-acrylic copolymer, polyacrylate, polymethacrylate,
Polyvinyl butyral, polyacrylonitrile, polyacrylamide, acrylonitrile-butadiene copolymer, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer,
Addition polymers such as polysulfone, polyether sulfone, silicone resin, etc. are used as appropriate, and they can be used as a species or as a mixture of two or more kinds.
これらの中でも、ポリカーボネート樹脂、特に一般式（
ＴＶ）
（式中、Ｒ２，Ｒ３，Ｒ’、Ｒ５，Ｒ’、Ｒ７Ｒ８，Ｒ
９は同一もしくは相異なる、水素原子、ハロゲン原子又
はアルキル基を示す。）で示される繰り返し単位を有す
るポリカーボネート樹脂（これは一般にポリカーボネー
トＺ樹脂と称される）を用いた場合に、塗料の保存安定
性が優れ、塗工時の欠陥発生が少なく好適である。Among these, polycarbonate resins, especially those with the general formula (
TV) (wherein, R2, R3, R', R5, R', R7R8, R
9 represents a hydrogen atom, a halogen atom, or an alkyl group, which are the same or different. ) When using a polycarbonate resin having a repeating unit represented by the formula (generally referred to as polycarbonate Z resin), the storage stability of the paint is excellent and defects are less likely to occur during coating, so it is suitable.
一般式（ｒＶ）において、Ｒ２−Ｒ９は同一もしくは相
異なる、水素原子、ハロゲン原子又はアルキル基を示す
が、ハロゲン原子としては、フッ素、塩素、臭素、ヨウ
素のいずれでもよく、好ましくは塩素原子である。また
、アルキル基を示す場合は、炭素数１〜４の直鎮もしく
は分枝のアルキル基であり、具体的にはメチル、エチル
、ｎ−プロピル、イソプロピル、ｎ−ブチル等が挙げら
れ、好ましくはメチルである。In the general formula (rV), R2-R9 represent the same or different hydrogen atoms, halogen atoms, or alkyl groups, and the halogen atom may be any of fluorine, chlorine, bromine, and iodine, and is preferably a chlorine atom. be. Further, when an alkyl group is indicated, it is a straight or branched alkyl group having 1 to 4 carbon atoms, and specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, etc., and preferably It is methyl.
このようなポリカーボネー）Ｚ樹脂は、公知の方法によ
り容易に得ることができ（アンゲバンテ・ケミ−１６８
巻、６３３頁（１９５６年））、又は市販のものとして
三菱瓦斯化学■製又は帝人化成■製等を用いても良い。Such a polycarbonate Z resin can be easily obtained by a known method (Angevante Chemie 168
Vol., p. 633 (1956)), or commercially available products such as those manufactured by Mitsubishi Gas Chemicals (2) or Teijin Chemicals (2) may be used.
前記一般式（ＩＶ）で示される繰り返し単位を有する化
合物のようにポリカーボネート樹脂の主鎖中にシクロヘ
キシル基を導入することにより、その滑り抵抗を少なく
でき、又ガラス転移点を変化させることなく強靭さを増
すことが可能となり、該ポリカーポネー）Ｚ樹脂を用い
た電子写真感光体は電子写真プロセスにおいて、トナー
、紙、クリーニングブレード等による摩耗を最小限に抑
えることが可能となる。本発明に用いられる一般式（Ｔ
Ｖ）で示される繰り返し単位を有するポリカーボネート
樹脂を具体的に例示すると次のものが挙げられるが、本
発明はこれらに限定されるものではない。By introducing a cyclohexyl group into the main chain of a polycarbonate resin, as in the case of a compound having a repeating unit represented by the general formula (IV), the slip resistance can be reduced, and the toughness can be improved without changing the glass transition point. The electrophotographic photoreceptor using the polycarbonate Z resin can minimize wear caused by toner, paper, cleaning blades, etc. in the electrophotographic process. General formula (T
Specific examples of polycarbonate resins having repeating units represented by V) include the following, but the present invention is not limited thereto.
Ｃ１
しＩ
これらのポリカーボネートＺ樹脂の分子量は数平均分子
量で５千乃至１０万が好ましい。これよりも小さいと機
械的強度が得られなくなり、耐摩耗性は期待できない。C1 I These polycarbonate Z resins preferably have a number average molecular weight of 5,000 to 100,000. If it is smaller than this, mechanical strength cannot be obtained and wear resistance cannot be expected.
また１０万よりも大きいと塗工時に粘度が大きくなりす
ぎ、作業性の困難を生じる。ガラス転移点は５０℃乃至
２００℃であり、この範囲において耐摩耗性が改善され
る。これよりもガラス転移点が低いと環境特性が低下し
好ましくない。また２００℃よりも高いと脆さが生じる
ようになり、摩耗劣化が激しくなる。Moreover, if it is larger than 100,000, the viscosity becomes too large during coating, resulting in difficulty in workability. The glass transition point is 50°C to 200°C, and wear resistance is improved within this range. If the glass transition point is lower than this, the environmental properties will deteriorate, which is not preferable. Moreover, if the temperature is higher than 200°C, brittleness will occur and wear and deterioration will be severe.
上記結合剤の使用量は一般式（Ｉ）で示される新規シリ
ルメチル化トリアリールアミン化合物に対して０．１乃
至３重量比であり、好ましくは０．１乃至２重量比であ
る。結合剤の量がこれよりも大であると、電荷輸送層に
おける電荷輸送材濃度が小さくなり、感度が悪くなる。The amount of the binder used is 0.1 to 3, preferably 0.1 to 2, by weight relative to the novel silylmethylated triarylamine compound represented by general formula (I). If the amount of binder is greater than this, the concentration of the charge transport material in the charge transport layer will be low, resulting in poor sensitivity.
又、本発明においては、必要に応じて前記の公知の電荷
輸送材を組み合わせて用いることもできる。Further, in the present invention, the above-mentioned known charge transport materials can be used in combination as necessary.
電荷輸送層の塗工手段は、特に限定されることはなく、
例えば、デイツプコーター、バーコータ、カレンダーコ
ーター、グラビアコーター、スピンコーター、等を適宜
使用することができ、又、電着塗装することも可能であ
る。The method for applying the charge transport layer is not particularly limited.
For example, a dip coater, bar coater, calendar coater, gravure coater, spin coater, etc. can be used as appropriate, and electrodeposition coating can also be used.
このようにして形成される電荷輸送層の膜厚は、１０乃
至５０μｍが好ましく、更に好ましくは１０乃至３０μ
ｍである。膜厚が５０μｍよりも大であると、電荷の輸
送により多くの時間を要するようになり、又、電荷が捕
獲される確率も大となり感度低下の原因となる。一方、
１０μｍより小であると、機械的強度が低下し、感光体
の寿命が短いものとなり好ましくない。The thickness of the charge transport layer formed in this way is preferably 10 to 50 μm, more preferably 10 to 30 μm.
It is m. If the film thickness is greater than 50 μm, it will take more time to transport the charge, and the probability that the charge will be captured will also increase, causing a decrease in sensitivity. on the other hand,
If it is smaller than 10 μm, the mechanical strength will decrease and the life of the photoreceptor will be shortened, which is not preferable.
以上のごとくにして一般式（Ｉ）で示される新規シリル
メチル化トリアリールアミン化合物を電荷輸送層に含む
電子写真感光体を作製することができるが、本発明では
更に導電性支持体と電荷発生層の間に必要に応じて、下
引き層、接着層、バリヤー層等を設けることもでき、こ
れらの層には例えばポリビニルブチラール、フェノール
樹脂、ポリアミド樹脂等の絶縁性樹脂や、導電性無機微
粉末を絶縁性樹脂に分散させたもの、あるいはポリピロ
ールやポリチオフェンのような共役系高分子にイオンド
ープし導電性高分子にしたもの等いずれも使用すること
ができる。又、感光体表面に表面保護層を設けることも
でき、前記下引き層等と同様の材料を用いることができ
る。As described above, an electrophotographic photoreceptor containing the novel silylmethylated triarylamine compound represented by the general formula (I) in the charge transport layer can be produced. If necessary, an undercoat layer, an adhesive layer, a barrier layer, etc. can be provided between the layers, and these layers may be made of insulating resins such as polyvinyl butyral, phenol resin, polyamide resin, or conductive inorganic fine powder. It is possible to use either a material obtained by dispersing the material in an insulating resin, or a material obtained by doping ions into a conjugated polymer such as polypyrrole or polythiophene to make a conductive polymer. Further, a surface protective layer can be provided on the surface of the photoreceptor, and the same material as the undercoat layer and the like can be used.
こうして得られた電子写真感光体の使用に際しては、ま
ず感光体表面をコロナ帯電器等により負に帯電せしめる
。帯電後、露光されることにより電荷発生層内で電荷が
発生し、正電荷が電荷輸送層内に注入され、これが電荷
輸送層中を通って表面にまで輸送され、表面の負電荷が
中和される。When using the electrophotographic photoreceptor thus obtained, first the surface of the photoreceptor is negatively charged using a corona charger or the like. After being charged, charges are generated in the charge generation layer by exposure to light, and positive charges are injected into the charge transport layer, which are transported through the charge transport layer to the surface, neutralizing the negative charges on the surface. be done.
一方、露光されなかった部分には負電荷が残ることにな
る。正規現像の場合、正帯電トナーが用いられ、この負
電荷が残った部分にトナーが付着し現像されることにな
る。反転現像の場合は、負帯電トナーが用いられ、電荷
が中和された部分にトナーが付着し、現像されることに
なる。本発明における電子写真感光体はいずれの現像方
法においても使用可能であり、高画質を与えることがで
きる。On the other hand, negative charges will remain in the unexposed areas. In the case of regular development, positively charged toner is used, and the toner adheres to the areas where this negative charge remains and is developed. In the case of reversal development, negatively charged toner is used, and the toner adheres to the neutralized portion and is developed. The electrophotographic photoreceptor of the present invention can be used in any developing method and can provide high image quality.
又、本発明においては、導電性支持体上にまず電荷輸送
層を設け、その上に電荷発生層を設けて電子写真感光体
を作製することもできる。この場合には、まず感光体表
面を正に帯電せしめ、露光後、発生した負電荷は感光体
の表面電荷を中和し、正電荷は電荷輸送層を通って導電
性支持体に輸送されることになる。Further, in the present invention, an electrophotographic photoreceptor can be produced by first providing a charge transport layer on a conductive support and then providing a charge generation layer thereon. In this case, the surface of the photoreceptor is first positively charged, and after exposure, the generated negative charges neutralize the surface charges of the photoreceptor, and the positive charges are transported to the conductive support through the charge transport layer. It turns out.
又、本発明においては、電荷発生材と電荷輸送材とを同
一層に含む単層型感光体とすることもでき、その場合に
は電荷発生材と電荷輸送材とを結合剤とともに、溶解、
分散せしめ、支持体上に１０乃至３０μｍの膜厚で塗工
せしめればよい。In addition, in the present invention, a single-layer type photoreceptor containing a charge generating material and a charge transporting material in the same layer can be used. In that case, the charge generating material and the charge transporting material are dissolved together with a binder.
It may be dispersed and coated on a support in a film thickness of 10 to 30 μm.
〔実施例〕
以下、実施例、比較例により本発明を具体的に説明する
が、本発明はこれら実施例に限定されるものではない。[Examples] Hereinafter, the present invention will be specifically explained with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
実施例−１
トリス（４−ジフェニルアミノフェニルメチル）メチル
シラン（例示化合物（１）の合成）撹拌装置、冷却管、
窒素導入管、滴下漏斗を備え付けた２ ００ｍｌ！１４
ツロフラスコにマグネシウム金属０．６ ｇ （２４，
９ｍｍｏ １）を入れ窒素置換を行った。ついでジエチ
ルエーテル１００−を入れ撹拌を開始した。そこへ４−
クロロメチル） ＩＪフェニルアミン５．９ ｇ （２
０ｍｍｏ １）を溶解したジエチルエーテル溶液２０ｍ
１をゆっくり滴下した。約５−滴下したところでゆるや
かに還流が始まった。還流させながら、さらにジエチル
エーテル溶液の滴下を続け、滴下終了後、更に１時間還
流を行った。以上のようにして得られたグリニヤール試
薬溶液を室温にまで戻し、次にジクロロジメチルシラン
１． Ｏｇ （６，７ｍｍｏ ］ ）のジエチルエーテ
ル溶液２０ｒｎｌを氷冷下ゆっくり滴下した。Example-1 Tris(4-diphenylaminophenylmethyl)methylsilane (synthesis of exemplified compound (1)) Stirring device, cooling tube,
200ml with nitrogen inlet tube and dropping funnel! 14
0.6 g of magnesium metal (24,
9 mmol 1) was added and nitrogen substitution was performed. Then, 100% of diethyl ether was added and stirring was started. There 4-
Chloromethyl) IJ phenylamine 5.9 g (2
20m of diethyl ether solution in which 0mmo 1) was dissolved
1 was slowly added dropwise. After approximately 5 drops, reflux began slowly. While the mixture was being refluxed, the diethyl ether solution was further added dropwise, and after the addition was completed, refluxing was further continued for 1 hour. The Grignard reagent solution obtained as above was returned to room temperature, and then dichlorodimethylsilane 1. 20 rnl of a diethyl ether solution of Og (6,7 mmo ) was slowly added dropwise under ice cooling.
滴下終了後、反応混合物を２時間還流し反応を熟成した
。その後、水５０−を水冷下漬下し加水分解を行った。After completion of the dropwise addition, the reaction mixture was refluxed for 2 hours to age the reaction. Thereafter, the mixture was soaked in 50% of water for hydrolysis.
次に、エーテル層を抽出し飽和炭酸水素ナトリウム水溶
液で１回、水で２回洗浄し、ついで無水硫酸す）ＩＪウ
ムで乾燥した。乾燥後、ジエチルエーテルを溜去し白色
固体を得た。該白色固体をｎ−へキサン／トルエン（１
／１）で再結晶し目的物を３．８ｇ得た（収率７０％）
。Next, the ether layer was extracted, washed once with saturated aqueous sodium bicarbonate solution and twice with water, and then dried over anhydrous sulfuric acid. After drying, diethyl ether was distilled off to obtain a white solid. The white solid was dissolved in n-hexane/toluene (1
/1) to obtain 3.8g of the target product (yield 70%)
.
融点、１９７．４〜１９９．２℃
元素分析； （Ｃ５＝Ｈ５１Ｎ−３ｉ ）計算値（％
） 実測値（％）
Ｃ８５，１９８５，０１
Ｈ６，２４６，３５
Ｎ ５．１４ ５．０６Ｓｉ ３
．４３ ３．５８実施例−２〜２０
例示化合物（２）〜（２０）については、実施例−１と
同様の方法でそれぞれ対応するクロロメチルトリアリー
ルアミン化合物及びトリクロロシラン化合物を用いて合
成し、融点測定及び元素分析を行なった。その結果を表
−１に示した。Melting point, 197.4-199.2℃ Elemental analysis; (C5=H51N-3i) Calculated value (%
) Actual value (%) C85,1985,01 H6,246,35 N 5.14 5.06Si 3
．． 43 3.58 Examples 2 to 20 Exemplary compounds (2) to (20) were synthesized in the same manner as in Example 1 using the corresponding chloromethyltriarylamine compound and trichlorosilane compound, Melting point measurements and elemental analyzes were performed. The results are shown in Table-1.
表−１
表−１の続き
表−１の続き
実施例−２１
ｘ型無金属フタロシアニン４．１ｇ、ポリビニルブチラ
ール（エスレックＢＭ−２、積木化学側製）４．１ｇ、
シクロへキサノン２００ ｇ、ガラスピーズ（１φ）６
５０ｇをサンドミルに入れ、４時間溶解、分散を行い、
電荷発生層用塗料を作製した。Table-1 Continuation of Table-1 Continuation of Table-1 Example-21 4.1 g of x-type metal-free phthalocyanine, 4.1 g of polyvinyl butyral (S-LEC BM-2, manufactured by Block Chemical),
200 g of cyclohexanone, 6 glass beads (1φ)
Put 50g into a sand mill, dissolve and disperse for 4 hours,
A paint for the charge generation layer was prepared.
該塗料を用い表面鏡面仕上げしたアルミニウムシリンダ
ー（４０φ）に乾燥後の膜厚が０．１５μｍになるよう
に浸漬塗工し、乾燥した。The paint was dip-coated onto an aluminum cylinder (40φ) whose surface had been mirror-finished so that the film thickness after drying was 0.15 μm, and then dried.
次に、実施例−１で合成した例示化合物（１）８０ｇ、
式（３３）で示される繰り返し単位を有するポリカーボ
ネートＺ樹脂（数平均分子量：５万）８０ｇをジオキサ
ン４５０ｇに溶解し、電荷輸送層用塗料を作製した。該
塗料を用いて、先に電荷発生層を塗工したアルミニウム
シリンダーに乾燥後の膜厚が２５μｍになるように浸漬
塗工し、乾燥した。Next, 80 g of the exemplary compound (1) synthesized in Example-1,
A paint for a charge transport layer was prepared by dissolving 80 g of polycarbonate Z resin (number average molecular weight: 50,000) having a repeating unit represented by formula (33) in 450 g of dioxane. The paint was applied by dip coating onto an aluminum cylinder previously coated with a charge generation layer so that the film thickness after drying would be 25 μm, and then dried.
このようにして作製したドラム状電子写真感光体を用い
、ドラムゼログラフィー試験機にて電子写真特性を評価
した。−５，５ｋ Ｖのコロナ電圧で帯電させたところ
、初期表面電位Ｖ。は−８８０Ｖであった。暗所にて２
秒放置後の表面電位ｖ２は一８６０Ｖとな、た。ついで
発信波長７９０ｎｍの半導体レーザーを照射し、半減露
光量Ｅｌ、□を求めたところ、０．２８μＪ／ｃＩＩ！
であり、残留電位Ｖ、は−７，１Ｖであった。Using the drum-shaped electrophotographic photoreceptor thus produced, electrophotographic properties were evaluated using a drum xerography tester. When charged with a corona voltage of -5.5 kV, the initial surface potential was V. was -880V. In the dark 2
The surface potential v2 after being left for seconds was -860V. Next, we irradiated it with a semiconductor laser with an emission wavelength of 790 nm and determined the half-decreased exposure amount El, □, which was 0.28 μJ/cII!
The residual potential V was -7.1V.
次に、５万回上記摸作を繰り返した後、Ｖｏ１ｖ２、Ｅ
、、□、■、を測定したところ、それぞれ−８６０Ｖ、
−８４０Ｖ、 ０．２８μＪ／ｃｎｆ、 −９゜０Ｖ
であり、感光体の性能は殆ど衰えていなかった。Next, after repeating the above simulation 50,000 times, Vo1v2, E
, □, ■ were measured, respectively -860V,
-840V, 0.28μJ/cnf, -9°0V
Therefore, the performance of the photoreceptor had hardly deteriorated.
次に、上記と同じ方法で作製した電子写真感光体をブレ
ードクリーニング方式で反転現像方式の市販のレーザー
ビームプリンターに装着しプリントテストを行った。そ
の結果、５万枚プリント後も膜厚の減少は殆ど見られず
、画像に影響を及ぼす傷も見あたらなかった。又、画像
も高画像濃度を維持し劣化はみられなかった。Next, the electrophotographic photoreceptor produced in the same manner as above was attached to a commercially available laser beam printer using a reversal development method using a blade cleaning method, and a print test was performed. As a result, almost no decrease in film thickness was observed even after printing 50,000 copies, and no scratches that affected the images were found. Moreover, the image maintained a high image density and no deterioration was observed.
このようにして本発明による電子写真感光体は感度、耐
久性の点で非常に優れていることが分かった。Thus, it has been found that the electrophotographic photoreceptor according to the present invention is extremely excellent in sensitivity and durability.
実施例−２２〜２９
実施例−２１において電荷輸送材として例示化合物（１
）のかわりに、表−２に示した化合物を用いる以外は同
様にして感光体を作製し、性能評価を行った。その結果
を表−２に示した。Examples-22 to 29 In Example-21, the exemplified compound (1
) Photoreceptors were prepared in the same manner except that the compounds shown in Table 2 were used, and the performance was evaluated. The results are shown in Table-2.
これかられかるように、いずれも初期、５万回繰り返し
後も感光体特性は優れたものであった。As will be seen, the photoreceptor properties were excellent initially and even after 50,000 repetitions.
また、プリンター内装着での５万枚プリント試験後でも
膜厚の減少はいずれの感光体においても見ることができ
ず、高画像濃度を維持していた。Further, even after a 50,000-sheet print test with the photoreceptor installed inside the printer, no decrease in film thickness was observed on any of the photoreceptors, and high image density was maintained.
表−２
実施例−３０〜３２
実施例−２１において、式（３３）で示される繰り返し
単位を有するポリカーボネー）Ｚ樹脂のかわりに、表−
３に示したポリカーボネー）Ｚ樹脂を用いる以外は同様
にして感光体を作製し、性能評価を行った。その結果を
表−３に示した。Table-2 Examples-30 to 32 In Example-21, instead of the polycarbonate (Z) resin having the repeating unit represented by formula (33), Table-
A photoreceptor was prepared in the same manner except that the polycarbonate Z resin shown in No. 3 was used, and its performance was evaluated. The results are shown in Table-3.
これかられかるように、いずれも初期、５万回繰り返し
後も感光体特性は優れたものであった。As will be seen, the photoreceptor properties were excellent initially and even after 50,000 repetitions.
また、プリンター内装着での５万回プリント試験後でも
膜厚の減少は、いずれの感光体においても見ることがで
きず高画像濃度を維持していた。Furthermore, even after a 50,000-time printing test in which the photoreceptors were mounted inside a printer, no decrease in film thickness was observed on any of the photoreceptors, and high image density was maintained.
表−３
実施例−３３
ポリアミド樹脂（アミランＣＭ−８０００、東し■製）
１０ｇをメタノール／ｎ−ブタノール（２／１）２００
ｇに溶解し、下引き履用塗料を作製した。該塗料を用い
表面鏡面仕上げしたアルミニウムシリンダー（４０φ）
に乾燥後の膜厚が０．１μｍになるように浸漬塗工し、
乾燥した。Table-3 Example-33 Polyamide resin (Amilan CM-8000, manufactured by Toshi ■)
10g methanol/n-butanol (2/1) 200
g to prepare an undercoating paint. Aluminum cylinder (40φ) whose surface was mirror-finished using this paint.
Dip coating was applied so that the film thickness after drying was 0.1 μm,
Dry.
次に、Ｘ型無金属フタロシアニン２０ｇ１例示化合物（
１）８０ｇ、式（３３）で示される繰り返し単位を有す
るポリヵーボネー）Ｚ樹脂（数平均分子量；５万）８０
ｇ、ジオキサン４５０ｇ、ガラスピーズ（１φ）６５０
ｇをサンドミルに入れ、４時間溶解、分散を行い、単層
用塗料を作製した。該塗料を用い、先に下引き層を塗工
したアルミニウムシリンダー（４０φ）に乾燥後の膜厚
が２５μｍになるように浸漬塗工し、乾燥した。Next, 20 g of X-type metal-free phthalocyanine 1 exemplified compound (
1) 80g, polycarbonate having a repeating unit represented by formula (33)) Z resin (number average molecular weight: 50,000) 80
g, dioxane 450g, glass beads (1φ) 650
g was placed in a sand mill and dissolved and dispersed for 4 hours to produce a single layer paint. Using this paint, it was dip coated onto an aluminum cylinder (40φ) to which an undercoat layer had been previously applied so that the film thickness after drying would be 25 μm, and then dried.
このようにして作製したドラム状電子写真感光体を用い
、ドラムゼログラフィー試験機にて電子写真特性を評価
した。−５，５ｋ Ｖのコロナ電圧で帯電させたところ
、初期表面電位Ｖ。は−８５０■であった。暗所にて２
秒放置後の表面電位Ｖ。Using the drum-shaped electrophotographic photoreceptor thus produced, electrophotographic properties were evaluated using a drum xerography tester. When charged with a corona voltage of -5.5 kV, the initial surface potential was V. was -850■. In the dark 2
Surface potential V after standing for seconds.
は−８４０Ｖとなった。ついで発信波長７９０ｎｍの半
導体レーザーを照射し、半減露光量Ｅ１７２を求めたと
ころ、０．３４μＪ／ｃｔｌであり、残留電位Ｖ１は−
１０，６Ｖであった。became -840V. Next, a semiconductor laser with an emission wavelength of 790 nm was irradiated, and the half-decreased exposure amount E172 was determined to be 0.34 μJ/ctl, and the residual potential V1 was -
It was 10.6V.
次に、５万回上記操作を繰り返した後、ＶＯｓＶ ２
、Ｅｌ／２ 、ＶＲを測定したところ、それぞれ８３０
Ｖ、 −８１０Ｖ、 ０．３５μＪ／ｃｎ！、−２２，
６ｖであり、感光体の性能は殆ど衰えていなかった。Next, after repeating the above operation 50,000 times, VOsV 2
, El/2, and VR were measured and found to be 830, respectively.
V, -810V, 0.35μJ/cn! , -22,
6V, and the performance of the photoreceptor was hardly degraded.
次に、上記と同じ方法で作製した電子写真感光体をブレ
ードクリーニング方式で反転現像方式の市販のレーザー
ビームプリンターに装着しプリントテストを行った。そ
の結果、５万枚プリント後も膜厚の減少は殆ど見られず
、画像に影響を及ぼす傷も見あたらなかった。又、画像
も高画像濃度を維持し劣化はみられなかった。Next, the electrophotographic photoreceptor produced in the same manner as above was attached to a commercially available laser beam printer using a reversal development method using a blade cleaning method, and a print test was performed. As a result, almost no decrease in film thickness was observed even after printing 50,000 copies, and no scratches that affected the images were found. Moreover, the image maintained a high image density and no deterioration was observed.
このようにして本発明による電子写真感光体は感度、耐
久性の点で非常に優れていることが分かった。Thus, it has been found that the electrophotographic photoreceptor according to the present invention is extremely excellent in sensitivity and durability.
実施例−３４
ジブロモアントアントロン５ｇ１ブチラール樹脂（エス
レックＢＭ−２．積水化学■製５ｇをシクロへキサノン
９０ｍ１に溶解、分散しボールミル中で２４時間混練し
た。得られた分散液をアルミ板上にバーコーターにて乾
燥後の膜厚が０．１５μｍになるように塗布し、乾燥さ
せ、電荷発生層を形成した。次に、例示化合物（１）５
ｇ、ポリカーボネートＡ樹脂（レキサン１３１−１ＬＬ
エンジニアリングプラスチツクス■製）５ｇをジオキサ
ン９０−に溶解し、これをさきに形成した電荷発生層上
にブレードコーターにて乾燥後の膜厚が２５μｍになる
ように塗布して乾燥させ電荷輸送層を形成した。Example 34 5 g of dibromoanthanthrone and 5 g of butyral resin (manufactured by S-LEC BM-2. Sekisui Chemical Co., Ltd.) were dissolved and dispersed in 90 ml of cyclohexanone and kneaded for 24 hours in a ball mill.The resulting dispersion was placed on an aluminum plate with a bar. A charge generation layer was formed by coating with a coater so that the film thickness after drying was 0.15 μm.Next, Exemplary Compound (1) 5
g, Polycarbonate A resin (Lexan 131-1LL
Engineering Plastics ■) was dissolved in dioxane 90-, and this was applied onto the previously formed charge generation layer using a blade coater so that the film thickness after drying would be 25 μm, and dried to form a charge transport layer. Formed.
このようにして作製した電子写真感光体を■ノ日電気製
作所製、静電複写紙試験装置ＥＰＡ−８１００を用いて
、−５，５ｋＶのコロナ電圧で帯電させたところ、初期
表面電位Ｖ。は−８８０Ｖであった。暗所にて２秒放置
後の表面電位Ｖ２は一８７０Ｖとなった。ついで照度５
１ｕｘのハロゲンランプを照射し、半減露光量Ｅ１７２
を求めたところ、１．０１ｕｘ−ｓｅｃであり、残留電
位■１は−７，６Ｖであった。When the electrophotographic photoreceptor thus prepared was charged with a corona voltage of -5.5 kV using an electrostatic copying paper tester EPA-8100 manufactured by Nonikichi Denki Seisakusho, the initial surface potential was V. was -880V. The surface potential V2 after being left in the dark for 2 seconds was -870V. Then illuminance 5
Irradiated with a 1ux halogen lamp, half-reduced exposure amount E172
was determined to be 1.01 ux-sec, and the residual potential (1) was -7.6V.
次に、５千回上記操作を繰り返した後、Ｖｏ、Ｖ ２
、Ｅｌ／２ 、Ｖｍを測定したところ、それぞれ−８７
０Ｖ、−８５０Ｖ、１．１１ｕｘ−ｓｅｃ。Next, after repeating the above operation 5,000 times, Vo, V 2
, El/2, and Vm were measured and found to be -87, respectively.
0V, -850V, 1.11ux-sec.
１５、３ Ｖであり、感光体の性能は殆ど衰えていなか
った。The voltage was 15.3 V, and the performance of the photoreceptor had hardly deteriorated.
実施例−３５〜４２
実施例−３４において電荷輸送材として例示化合物（１
）のかわりに、表−４に示した化合物を用いる以外は同
様にして感光体を作製し、性能評価を行った。その結果
を表−４に示した。Examples-35 to 42 In Example-34, the exemplified compound (1
) Photoreceptors were prepared in the same manner except that the compounds shown in Table 4 were used, and the performance was evaluated. The results are shown in Table-4.
表
実施例−４３〜５４
例示化合物（２１）、（２２）、く２３）、（２４）、
（２５）、 （２６）、 （２７）、 （２８）、
（２９）、 （３０）、 （３１）、 （３２）につい
ては、実施例−１と同様の方法により合成することがで
きる。Table Examples-43 to 54 Exemplary compounds (21), (22), 23), (24),
(25), (26), (27), (28),
(29), (30), (31), and (32) can be synthesized by the same method as in Example-1.
また、実施例−２１、実施例−３３、実施例３４におい
て、電荷輸送材として例示化合物（１）のかわりに、こ
れら例示化合物（２１）〜（３２）を用いる以外は同様
にして感光体を作製し、性能評価を行なうと、実施例−
２１、実施例３３、実施例−３４の場合と同様に、感度
、耐久性の点で非常に優れた結果が得られる。In addition, in Example 21, Example 33, and Example 34, the photoreceptor was prepared in the same manner except that these exemplified compounds (21) to (32) were used instead of exemplified compound (1) as the charge transport material. After fabrication and performance evaluation, Example-
As in the case of Example 21, Example 33, and Example 34, very excellent results are obtained in terms of sensitivity and durability.
比較例−１
実施例−２１において電荷輸送材として例示化合物（１
）のかわりに、４，４”、４”−トリメチルトリフェニ
ルアミンを用いる以外は同様にして感光体を作製し、性
能評価を行った。Comparative Example-1 Example compound (1) was used as a charge transport material in Example-21.
) A photoreceptor was prepared in the same manner except that 4,4'',4''-trimethyltriphenylamine was used, and the performance was evaluated.
−５，５ｋＶのコロナ電圧で帯電させたところ、初期表
面電位Ｖ。は−８８０Ｖであった。暗所にて２秒放置後
の表面電位Ｖ２は一８６０Ｖとなった。ついで発信波長
７９０ｎｍの半導体レーザーを照射し、半減露光量Ｅ１
７．を求めたところ、０゜８９μＪ／ｃ＋＋！であり、
残留電位Ｖ、は−４２，６Ｖであった。When charged with a corona voltage of -5.5 kV, the initial surface potential was V. was -880V. The surface potential V2 after being left in the dark for 2 seconds was -860V. Next, a semiconductor laser with a transmission wavelength of 790 nm is irradiated, and the exposure amount is reduced by half E1.
7. When I calculated it, it was 0゜89μJ/c++! and
The residual potential V was -42.6V.
次に、５万回上記操作を繰り返した後、Ｖｏ、Ｖ ２−
、 Ｅ ｌ／２ 、ＶＲを測定したところ、それぞれ８
６０Ｖ、−８２０Ｖ、０．９４μＪ／Ｃ［Ｉ！、−６３
，１Ｖであり、感光体の性能は実施例−２１に比較して
劣っていた。Next, after repeating the above operation 50,000 times, Vo, V 2-
, E l/2 and VR were measured and found to be 8, respectively.
60V, -820V, 0.94μJ/C [I! , -63
, 1V, and the performance of the photoreceptor was inferior to that of Example-21.
次に、上記と同じ方法で作製した電子写真感光体をブレ
ードクリーニング方式で反転現像方式の市販ル−ザービ
ームプリンターに装着しプリントテストを行った。その
結果、５万枚プリント後も膜厚の減少は殆ど見られず、
画像に影響を及ぼす傷も見あたらなかったが、感度が悪
いため画像濃度は薄いものであった。Next, the electrophotographic photoreceptor prepared in the same manner as above was mounted on a commercially available laser beam printer of reversal development method using a blade cleaning method, and a print test was performed. As a result, there was almost no decrease in film thickness even after printing 50,000 sheets.
Although no scratches affecting the image were found, the image density was low due to poor sensitivity.
Claims (4)
リアリールアミン化合物。 ▲数式、化学式、表等があります▼（ I ） （式中、Ａｒ＾１は置換されていてもよいアリーレン基
を示し、３つのＡｒ＾１は同一でも異なっていてもよい
。Ａｒ＾２は置換されていてもよいアリール基を示し、
６つのＡｒ＾２は同一でも異なっていてもよい。Ｒ＾１
は置換されていてもよいアルキル基、シクロアルキル基
、アラルキル基又はアリール基を示す。）(1) A novel silylmethylated triarylamine compound represented by the general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, Ar^1 represents an optionally substituted arylene group, and the three Ar^1s may be the same or different. Ar^2 is Indicates an optionally substituted aryl group,
The six Ar^2 may be the same or different. R^1
represents an optionally substituted alkyl group, cycloalkyl group, aralkyl group or aryl group. )
有し、Ｘ＾４はハロゲン原子を示す。） で示されるグリニャール試薬と、一般式（III）Ｘ＾１
Ｘ＾２Ｘ＾３ＳｉＲ＾１（III） （式中、Ｒ＾１は式（ I ）と同じ意味を有し、Ｘ＾１
、Ｘ＾２、Ｘ＾３はハロゲン原子又はアルコキシ基を示
す。） で示される３官能シラン化合物を反応せしめることを特
徴とする請求項（１）記載の新規シリルメチル化トリア
リールアミン化合物の製造方法。(2) General formula (II) ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ (II) (In the formula, Ar^1 and Ar^2 have the same meaning as in formula (I), and X^4 is a halogen atom. ) and the Grignard reagent represented by the general formula (III)
X^2X^3SiR^1(III) (wherein, R^1 has the same meaning as in formula (I), and X^1
, X^2, and X^3 represent a halogen atom or an alkoxy group. 2. The method for producing a novel silylmethylated triarylamine compound according to claim 1, characterized in that a trifunctional silane compound represented by the following formula is reacted.
須の構成要素とする電子写真感光体において、請求項（
１）記載の新規シリルメチル化トリアリールアミン化合
物を感光層中に含むことを特徴とする電子写真感光体。(3) An electrophotographic photoreceptor comprising a conductive support and a photosensitive layer formed thereon as essential components, as claimed in claim (
1) An electrophotographic photoreceptor comprising the novel silylmethylated triarylamine compound described in 1) in a photosensitive layer.
須の構成要素とする電子写真感光体において、請求項（
１）記載の新規シリルメチル化トリアリールアミン化合
物及び一般式（IV）で示される繰り返し単位を有するポ
リカーボネート樹脂を感光層中に含むことを特徴とする
電子写真感光体。 ▲数式、化学式、表等があります▼（IV） （式中、Ｒ＾２、Ｒ＾３、Ｒ＾４、Ｒ＾５、Ｒ＾６、Ｒ
＾７、Ｒ＾８、Ｒ＾９は同一もしくは相異なる、水素原
子、ハロゲン原子又はアルキル基を示す。）(4) An electrophotographic photoreceptor comprising a conductive support and a photosensitive layer formed thereon as essential components, as claimed in (
An electrophotographic photoreceptor comprising the novel silylmethylated triarylamine compound described in 1) and a polycarbonate resin having a repeating unit represented by general formula (IV) in a photosensitive layer. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(IV) (In the formula, R^2, R^3, R^4, R^5, R^6, R
^7, R^8, and R^9 are the same or different and represent a hydrogen atom, a halogen atom, or an alkyl group. )
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2122543A JPH0421689A (en) | 1990-05-12 | 1990-05-12 | Novel organosilicon compound, its production and photo-sensitive material for electrophotography produced by using the same |
| US07/696,201 US5290963A (en) | 1990-05-12 | 1991-05-06 | Organic silicon compound, method of its production, and photoreceptor for electrophotography incorporating it |
| EP91107621A EP0457212A1 (en) | 1990-05-12 | 1991-05-10 | Novel organic silicon compound, method of its production, and photoreceptor for electrophotography incorporating it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2122543A JPH0421689A (en) | 1990-05-12 | 1990-05-12 | Novel organosilicon compound, its production and photo-sensitive material for electrophotography produced by using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0421689A true JPH0421689A (en) | 1992-01-24 |
Family
ID=14838476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2122543A Pending JPH0421689A (en) | 1990-05-12 | 1990-05-12 | Novel organosilicon compound, its production and photo-sensitive material for electrophotography produced by using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0421689A (en) |
-
1990
- 1990-05-12 JP JP2122543A patent/JPH0421689A/en active Pending
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