JPH0310255A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPH0310255A JPH0310255A JP14414589A JP14414589A JPH0310255A JP H0310255 A JPH0310255 A JP H0310255A JP 14414589 A JP14414589 A JP 14414589A JP 14414589 A JP14414589 A JP 14414589A JP H0310255 A JPH0310255 A JP H0310255A
- Authority
- JP
- Japan
- Prior art keywords
- group
- photoreceptor
- disazo
- binder
- groups
- 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
- 108091008695 photoreceptors Proteins 0.000 claims description 57
- 239000000126 substance Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000011230 binding agent Substances 0.000 abstract description 22
- 239000000463 material Substances 0.000 abstract description 18
- 238000000576 coating method Methods 0.000 abstract description 13
- 230000035945 sensitivity Effects 0.000 abstract description 12
- 239000011248 coating agent Substances 0.000 abstract description 11
- 125000000664 diazo group Chemical class [N-]=[N+]=[*] 0.000 abstract description 9
- 239000006185 dispersion Substances 0.000 abstract description 9
- 238000007738 vacuum evaporation Methods 0.000 abstract 2
- -1 disazo compound Chemical class 0.000 description 73
- 239000010410 layer Substances 0.000 description 33
- 239000002800 charge carrier Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 150000002484 inorganic compounds Chemical class 0.000 description 5
- 229910010272 inorganic material Inorganic materials 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000006163 transport media Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229920006267 polyester film Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-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
- YGBCLRRWZQSURU-UHFFFAOYSA-N 4-[(diphenylhydrazinylidene)methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 YGBCLRRWZQSURU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- DMDPKUWXJUYFKO-UHFFFAOYSA-N 1,1'-biphenyl;hydrochloride Chemical compound Cl.C1=CC=CC=C1C1=CC=CC=C1 DMDPKUWXJUYFKO-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- LMZMQXGQDGYBIS-UHFFFAOYSA-N 1-nitroxanthen-9-one Chemical compound O1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] LMZMQXGQDGYBIS-UHFFFAOYSA-N 0.000 description 1
- PXPBDJVBNWDUFM-UHFFFAOYSA-N 2,3,4,6-tetranitrophenol Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C([N+]([O-])=O)=C1[N+]([O-])=O PXPBDJVBNWDUFM-UHFFFAOYSA-N 0.000 description 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- WLFGGJFWKXTOGJ-UHFFFAOYSA-N 2,3-dihydroindol-1-amine Chemical compound C1=CC=C2N(N)CCC2=C1 WLFGGJFWKXTOGJ-UHFFFAOYSA-N 0.000 description 1
- JOERSAVCLPYNIZ-UHFFFAOYSA-N 2,4,5,7-tetranitrofluoren-9-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O JOERSAVCLPYNIZ-UHFFFAOYSA-N 0.000 description 1
- POJAQDYLPYBBPG-UHFFFAOYSA-N 2-(2,4,7-trinitrofluoren-9-ylidene)propanedinitrile Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=C(C#N)C#N)C2=C1 POJAQDYLPYBBPG-UHFFFAOYSA-N 0.000 description 1
- SJNWVJGWEJCMEY-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;phthalic acid Chemical compound OCCOCCO.OC(=O)C1=CC=CC=C1C(O)=O SJNWVJGWEJCMEY-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- JFJWVJAVVIQZRT-UHFFFAOYSA-N 2-phenyl-1,3-dihydropyrazole Chemical class C1C=CNN1C1=CC=CC=C1 JFJWVJAVVIQZRT-UHFFFAOYSA-N 0.000 description 1
- OQMROOTVLOXIJH-UHFFFAOYSA-N 3,4-dihydro-2h-quinolin-1-amine Chemical compound C1=CC=C2N(N)CCCC2=C1 OQMROOTVLOXIJH-UHFFFAOYSA-N 0.000 description 1
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 1
- YTJZGOONVHNAQC-UHFFFAOYSA-N 4-[(diphenylhydrazinylidene)methyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 YTJZGOONVHNAQC-UHFFFAOYSA-N 0.000 description 1
- UZGVMZRBRRYLIP-UHFFFAOYSA-N 4-[5-[4-(diethylamino)phenyl]-1,3,4-oxadiazol-2-yl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(CC)CC)O1 UZGVMZRBRRYLIP-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- LSZJZNNASZFXKN-UHFFFAOYSA-N 9-propan-2-ylcarbazole Chemical compound C1=CC=C2N(C(C)C)C3=CC=CC=C3C2=C1 LSZJZNNASZFXKN-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- GDXLHMIKVIFRSD-UHFFFAOYSA-N C=C1CN(C2=CCCCC2C1)N.C(C)N1C2=CC=CC=C2C=2C=CC=CC12 Chemical compound C=C1CN(C2=CCCCC2C1)N.C(C)N1C2=CC=CC=C2C=2C=CC=CC12 GDXLHMIKVIFRSD-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- MUBKMWFYVHYZAI-UHFFFAOYSA-N [Al].[Cu].[Zn] Chemical compound [Al].[Cu].[Zn] MUBKMWFYVHYZAI-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 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 1
- 230000005525 hole transport Effects 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
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- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920001959 vinylidene polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、電子写真用感光体に関し、更に詳しくは、ジ
スアゾ化合物を含有する感光層を有する電子写真用感光
体に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing a disazo compound.
光導電性物質と静電現象を結び付けて画像記録を行なう
、いわゆる電子写真法は、カールソンが米国特許第22
1776号に於いて明らかにした「エレクトロン フォ
トグラフィ」に端を発している。電子写真法では、光の
照射量に応じてその電気抵抗が変化する光導電物質を、
絶縁性のバインダー樹脂に分散し、これを支持体上に塗
布した光導電性材料が感光体として用いられる。この光
導電材料は、暗所でコロナ帯電により一様な、表面電荷
を与えられたのち、画像露光の明るさの値に応じた表面
電荷を失い静電潜像が形成される。この様な静電潜像は
、次にその表面が適当な検電表示物質、すなわちトナー
で処理されて可視像となる。トナーは乾燥担体と共に、
或いは有機溶剤中にコロイド状に懸濁して用いられ、静
電潜像の電荷に応じてクーロン力によって付着させるこ
とができる。付着した表示物質は、熱、圧力などにより
定着させることができる。So-called electrophotography, which combines photoconductive substances and electrostatic phenomena to record images, was developed by Carlson in U.S. Pat.
It originated from the ``electron photography'' that was revealed in issue 1776. In electrophotography, a photoconductive material whose electrical resistance changes depending on the amount of light irradiation is used.
A photoconductive material that is dispersed in an insulating binder resin and coated on a support is used as a photoreceptor. After this photoconductive material is given a uniform surface charge by corona charging in a dark place, it loses the surface charge depending on the brightness value of image exposure, and an electrostatic latent image is formed. The surface of such an electrostatic latent image is then treated with a suitable electrostatic indicator material, ie, toner, to form a visible image. The toner together with the dry carrier
Alternatively, it can be used as a colloidal suspension in an organic solvent, and can be attached by Coulomb force depending on the charge of the electrostatic latent image. The attached display substance can be fixed by heat, pressure, or the like.
また、静電潜像は第2の支持体(例えば、紙、フィルム
等)に転写し、現像、定着させることもできる。The electrostatic latent image can also be transferred to a second support (eg, paper, film, etc.), developed, and fixed.
この様な電子写真法に於いて、電子写真用感光体に要求
される基本的な特性としては、(1)暗所で適当な電位
に帯電できること、(2)暗所における電荷の保持能力
が大きいこと、(3)光照射によって速やかに電荷を散
逸できること、などが挙げられる。In such electrophotography, the basic characteristics required of an electrophotographic photoreceptor are (1) ability to be charged to an appropriate potential in the dark, and (2) ability to retain charge in the dark. and (3) the ability to quickly dissipate charge by light irradiation.
また、実用面からは、(4)適当な面積を持つ感光体が
容易に造れること、(5)繰り返し安定性が良いこと、
(6)耐久性があること、(7)安価なこと、などが要
求されている。In addition, from a practical standpoint, (4) a photoreceptor with an appropriate area can be easily manufactured, (5) it has good repeat stability,
(6) It must be durable, and (7) It must be inexpensive.
従来、電子写真用感光体の光導電性材料としては、セレ
ン、硫化カドミウム、酸化亜鉛などが広く用いられてき
た。しかしながら、これらの無機化合物は、多くの長所
を持つ反面、様々な欠点を有していることも事実である
。例えば、セレンは製造する条件が難しく、製造コスト
が高い、温度、湿度、指紋などにより容易に結晶化が進
み、感光体としての特性が劣化してしまう為に取り扱い
に注意を要するなどの欠点を持っていた。また、硫化カ
ドミウムは、特に耐湿性が悪く、感光体の吸湿を防止す
る為にヒーターを設置するなどの補助手段が必要であっ
た。また、酸化亜鉛は、硬度、耐摩耗性など機械的な強
度に問題がある他、ローズベンガルに代表される染料で
増感しているため、コロナ帯電による染料の光退色が感
光体の寿命を縮めていた。これらの無機化合物は、重金
属を含有し、取扱いを誤まると公害問題に発展する危険
性もあった。Conventionally, selenium, cadmium sulfide, zinc oxide, and the like have been widely used as photoconductive materials for electrophotographic photoreceptors. However, while these inorganic compounds have many advantages, they also have various disadvantages. For example, selenium has drawbacks such as difficult manufacturing conditions, high manufacturing costs, and the need for careful handling as it easily crystallizes due to temperature, humidity, fingerprints, etc., and deteriorates its properties as a photoreceptor. had. Further, cadmium sulfide has particularly poor moisture resistance, and auxiliary means such as installing a heater are required to prevent the photoreceptor from absorbing moisture. In addition, zinc oxide has problems with mechanical strength such as hardness and abrasion resistance, and since it is sensitized with dyes such as rose bengal, photobleaching of the dye due to corona charging can shorten the life of the photoreceptor. It was shrinking. These inorganic compounds contain heavy metals, and if handled incorrectly, there is a risk of developing a pollution problem.
近年、これらの無機化合物の光導電性材料の欠点を克服
する為に、種々の有機光導電性化合物を用いた電子写真
用感光体の研究開発が盛んに行なわれている。例えば、
ポリ−N−ビニルカルバゾールと2.4.7−)リニト
ロフルオレノンとからなる電子写真用感光体(米国特許
第3,484,237号)、ポIJ N−ビニルカル
バゾールをピリリウム塩系色素で増感したもの(特公昭
48−25658号)、染料と樹脂とからなる共晶体を
光導電性材料とするもの(特開昭47−10785号)
などがある。この様な有機化合物系電子写真用感光体は
、無機化合物系電子写真感光体に比べて、成膜が容易で
あり、極めて生産性が高く、安価な感光体を提供できる
と言う利点を持っている。しかしながら、例えば、ポI
J −N−ビニルカルバゾールの様な光導電性ポリマー
に関しては、ポリマー単独では被膜性、可撓性、接着性
などが不良であり、これらの欠点を改良する為に可塑材
、バインダーなどが添加されるが、この為に感度の低下
や、残留電位の上昇を招くなどの問題点があった。In recent years, in order to overcome the drawbacks of these inorganic compound photoconductive materials, research and development of electrophotographic photoreceptors using various organic photoconductive compounds has been actively conducted. for example,
Electrophotographic photoreceptor consisting of poly-N-vinylcarbazole and 2.4.7-)linitrofluorenone (U.S. Pat. No. 3,484,237), poly-IJ N-vinylcarbazole enhanced with pyrylium salt dye. (Japanese Patent Publication No. 48-25658), and one using a eutectic consisting of dye and resin as a photoconductive material (Japanese Patent Publication No. 47-10785)
and so on. Compared to inorganic compound-based electrophotographic photoreceptors, such organic compound-based electrophotographic photoreceptors have the advantage of being easier to form a film, have extremely high productivity, and can provide inexpensive photoreceptors. There is. However, for example, PoI
Regarding photoconductive polymers such as J-N-vinylcarbazole, the polymer alone has poor film properties, flexibility, and adhesion, so plasticizers, binders, etc. are added to improve these defects. However, this caused problems such as a decrease in sensitivity and an increase in residual potential.
また、有機化合物系の低分子光導電性化合物は、バイン
ダーの選択範囲も広く、適当なポリマーを選択すれば、
被膜性、接着性など機械的特性の優れたものを造ること
ができるが、反面、光感度、繰り返し特性など電子写真
用感光体としての要求を十分に満たずものではなかった
。In addition, organic compound-based low-molecular photoconductive compounds have a wide range of binders to choose from, and if an appropriate polymer is selected,
Although it is possible to produce products with excellent mechanical properties such as filmability and adhesion, on the other hand, they do not fully meet the requirements for electrophotographic photoreceptors, such as photosensitivity and repeatability.
本発明が解決しようとする課題は、従来の無機化合物系
電子写真用感光体の欠点を克服し、且つこれまで提案さ
れてきた有機化合物系電子写真用感光体の欠点を改良し
、十分に実用に供しうる程度の高感度、高耐久性を有す
る電子写真用感光体を提供することにある。The problem to be solved by the present invention is to overcome the drawbacks of conventional inorganic compound-based electrophotographic photoreceptors, and improve the drawbacks of the organic compound-based electrophotographic photoreceptors that have been proposed so far, so as to be fully practical. The object of the present invention is to provide an electrophotographic photoreceptor having high sensitivity and high durability that can be used for various purposes.
(課題を解決するための手段〕
本発明は上記課題を解決するために、
−形成(1)
(式中、Cpはカプラー残基を表わす。)で表わされる
化合物を含有する電子写真用感光体を提供する。(Means for Solving the Problems) In order to solve the above problems, the present invention provides an electrophotographic photoreceptor containing a compound represented by -Formation (1) (wherein, Cp represents a coupler residue). I will provide a.
一般式(I)で表わされる化合物に於りるカプラー残基
としては、公知のカプラー成分から選択することができ
るが、特に−形成(II)−形成(III)
一般式(TV)
3
H
又は−形成(V)
3
(式中、Xは、置換基を有していてもよい炭化水素環又
は複素環を表わし、Yは、
R2及びR3は各々独立的に水素原子、置換基を有して
いても良い炭化水素基又は複素環基を表わし、R1及び
R2は互いに環を形成していてもよい。)
で表わされるカプラー残基である場合が好ましい。The coupler residue in the compound represented by general formula (I) can be selected from known coupler components, but especially -formation (II) -formation (III) general formula (TV) 3 H or -Formation (V) 3 (wherein, X represents a hydrocarbon ring or a heterocycle which may have a substituent, Y is, R2 and R3 each independently have a hydrogen atom or a substituent) (R1 and R2 may mutually form a ring.) A coupler residue represented by the following formula is preferred.
上記−形成(n)、(III)、(TV)及び(V)の
カプラー残基におけるR1.R2及びR3の具体例とし
ては、メチル基、エチル基、プロピル基、ブチル基、ペ
ンチル基、ヘキシル基、イソプロピル基、イソブチル基
、イソアミル基、イソヘキシル基、ネオペンチル基、t
er t−ブチル基の如き炭素原子数1〜20のアルキ
ル基;フェニル基、ナフチル基の如き芳香族炭化水素基
;ピリジル基、カルバゾリル基、ベンゾトリアゾリル基
の如き芳香族複素環基等が挙げられる。R1. in the above-forming coupler residues of (n), (III), (TV) and (V). Specific examples of R2 and R3 include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, isopropyl group, isobutyl group, isoamyl group, isohexyl group, neopentyl group, t
Alkyl groups having 1 to 20 carbon atoms such as er t-butyl group; aromatic hydrocarbon groups such as phenyl group and naphthyl group; aromatic heterocyclic groups such as pyridyl group, carbazolyl group, benzotriazolyl group, etc. Can be mentioned.
R1、R2及びR3が置換アルキル基である場合の置換
基としては、例えば、ハロゲン原子、ニトロ原子、シア
ン基、ヒドロキシル基、置換ヒドロキシル基、チオール
基、置換チオール基、アミノ基、置換アミノ基、アリー
ル基等が挙げられる。When R1, R2 and R3 are substituted alkyl groups, examples of the substituent include a halogen atom, a nitro atom, a cyan group, a hydroxyl group, a substituted hydroxyl group, a thiol group, a substituted thiol group, an amino group, a substituted amino group, Examples include aryl groups.
0
これらの置換基を2個以」二有する置換アルキル基であ
ってもよい。置換アルキル基の具体例としては、クロロ
メチル基、トリフルオロメチル基、2ブロモエチル基の
如きハロゲノアルキル基;ニトロメチル基、3−二トロ
プロピル基の如きニトロアルキル基;シアノメチル基、
2−シアノエチル基の如きシアノアルキル基;ヒドロキ
シメチル基、2−ヒドロキシエチル栽、2−ヒドロキシ
プロピル基、3−ヒドロキシプロピル基の如きヒトロー
トジアルキル基;メトキシメチル基、2−メトキシエチ
ル基、エトキシメチル基、フェノキシメチル基の如き置
換ヒドロキシアルキル基;チオヒドロキシアルキル基、
2=ヂオヒドロキシェ−f−ル%の如きチオヒドロキシ
アルキル基;メチルチオメチル暴、2−メチルチオエチ
ル基の如き置換チオヒドロキシアルキル基;アミノメチ
ル基、2−アミノエチル基の如きアミノアルキル基;メ
チルアミノメチル基、エチルアミノメチル基、ジメチル
アミノメチル基、2−(ジメチルアミノ)エチル基、フ
ェニルアミノメチル基、ジフェニルアミノメチル基の如
き置JMアミノアルニ)−ル基等が2抄げられる。0 It may be a substituted alkyl group having two or more of these substituents. Specific examples of substituted alkyl groups include halogenoalkyl groups such as chloromethyl group, trifluoromethyl group, and 2-bromoethyl group; nitroalkyl groups such as nitromethyl group and 3-nitropropyl group; cyanomethyl group,
Cyanoalkyl groups such as 2-cyanoethyl group; Hydrodialkyl groups such as hydroxymethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group; Methoxymethyl group, 2-methoxyethyl group, ethoxymethyl group substituted hydroxyalkyl groups such as phenoxymethyl groups; thiohydroxyalkyl groups;
thiohydroxyalkyl group such as 2=diohydroxyl-f-; substituted thiohydroxyalkyl group such as methylthiomethyl, 2-methylthioethyl group; aminoalkyl group such as aminomethyl group, 2-aminoethyl group; methylaminomethyl 2, such as ethylaminomethyl group, dimethylaminomethyl group, 2-(dimethylamino)ethyl group, phenylaminomethyl group, diphenylaminomethyl group, and JM aminoalni)yl group.
R1、Rz及びR3が置換芳香族炭化水素基又は置換芳
香族複素環基である場合の置換基としては、アルキル基
、ハロゲン原子、二1・0栽、シアノ基、ヒドロキシル
基、置換ヒドロキシル基、チオール基、置換チオール基
、アミノ基、置換アミン基等が挙げられる。これらの置
換基を2個以−ト有する置換芳香族炭化水素基又は置換
芳香族複素環基であってもよい。When R1, Rz and R3 are a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group, examples of the substituent include an alkyl group, a halogen atom, a cyano group, a hydroxyl group, a substituted hydroxyl group, Examples thereof include a thiol group, a substituted thiol group, an amino group, and a substituted amine group. It may be a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group having two or more of these substituents.
R1,R2及びR3が置換フェニル基である場合の具体
例としては、トリル基、エチルフェニル基の如きアルキ
ルフェニル基;クロロフェニル暴、ブロモフェニル基の
如きハロゲン置換フェニル基;ニトロフェニル基;シア
ノフェニル% ; ヒト+:+ キシフェニル基;メト
キシフェニル基、工1−キシフェニル基の如き置換ヒド
ロキシフェニル基;チオヒドロキシフェニル基;メチル
チオフェニル基、エチルチオフェニル基の如き置換チオ
フェニル基;アミノフェニル基;メチルアミノフェニル
基、シ1 】
2
メチルアミノフェニル基、フェニルアミノフェニル基、
ジフェニルアミノフェニル基の如き置換アミノフェニル
基等が挙げられる。Specific examples of R1, R2 and R3 being substituted phenyl groups include alkylphenyl groups such as tolyl and ethylphenyl groups; halogen-substituted phenyl groups such as chlorophenyl and bromophenyl groups; nitrophenyl group; cyanophenyl% ; Human+:+ xyphenyl group; substituted hydroxyphenyl group such as methoxyphenyl group and 1-xyphenyl group; thiohydroxyphenyl group; substituted thiophenyl group such as methylthiophenyl group and ethylthiophenyl group; aminophenyl group; methylaminophenyl group group, 1 ] 2 methylaminophenyl group, phenylaminophenyl group,
Examples include substituted aminophenyl groups such as diphenylaminophenyl groups.
R’ 、R2及びR3が置換縮合芳香族炭化水素基であ
る場合の具体例としては、メチルナフチル基、エチルナ
フチル基の如きアルキルナフチル基;クロロナフチル基
、ブロモナフチル基の如きハロゲン置換ナフチル基;ヒ
ドロキシナフチル基;メトキシナフチル基、エトキシナ
フチル基の如き置換ヒドロキシナフチル基;チオヒドロ
キシナフチル基;メチルチオナフチル基、エチルチオナ
フチル基の如き置換チオナフチル暴;アミノナフチル暴
;メチルアミノナフチル基、ジメチルアミノナフチル基
、フェニルアミノナフチル基、ジフェニルアミノナフチ
ル基の如き置換アミノナフチル基等が挙げられる。Specific examples of R', R2 and R3 being substituted condensed aromatic hydrocarbon groups include alkylnaphthyl groups such as methylnaphthyl group and ethylnaphthyl group; halogen-substituted naphthyl groups such as chloronaphthyl group and bromonaphthyl group; Hydroxynaphthyl group; substituted hydroxynaphthyl group such as methoxynaphthyl group and ethoxynaphthyl group; thiohydroxynaphthyl group; substituted thionaphthyl group such as methylthionaphthyl group and ethylthionaphthyl group; aminonaphthyl group; methylaminonaphthyl group, dimethylaminonaphthyl group , a phenylaminonaphthyl group, a substituted aminonaphthyl group such as a diphenylaminonaphthyl group, and the like.
RI R2及びR3が置換芳香族複素環基、特に置換
ヘンヅチアゾリル基である場合の具体例としては、メチ
ルヘンヅチアゾリル基、エヂルヘンヅチアゾリル基の如
きアルキルヘンジチアプリル基;クロロヘンゾチアヅリ
ル基、ブロモヘンジチアゾリル基の如きハロゲン置換ヘ
ンジチアゾリル基;ニトロヘンゾチアゾリル基;シアノ
ヘンヅチアゾリル基;ヒドロキシヘンゾチアゾリル基;
メトキシヘンジチアゾリル基、工l・キジヘンジチアゾ
リル基の如き置換ヒドロキシヘンジチアゾリル基;チオ
ヒドロキシヘンヅチアゾリル基;メチルチオヘンジチア
ゾリル基、エチルチオヘンジチアゾリル基の如き置換チ
オヘンヅチアゾリル基;アミノヘンゾチアゾリル基;メ
チルアミノヘンジチアゾリル基、ジメチルアミノヘンジ
チアゾリル基、フェニルアミノベンゾチアゾリル基、ジ
フェニルアミノヘンゾチアヅリル基の如き置換アミノヘ
ンジチアゾリル基等が挙げられる。RI When R2 and R3 are substituted aromatic heterocyclic groups, particularly substituted hendithiazolyl groups, specific examples include alkylhendithiapril groups such as methylhendithiazolyl group and edylhendithiazolyl group; chlorohendithiazolyl group; halogen-substituted hendithiazolyl groups such as duryl and bromohendithiazolyl groups; nitrohenzothiazolyl groups; cyanohenzothiazolyl groups; hydroxyhenzothiazolyl groups;
Substituted hydroxyhendithiazolyl group such as methoxyhendithiazolyl group, methoxyhendithiazolyl group; thiohydroxyhendithiazolyl group; methylthiohendithiazolyl group, ethylthiohendithiazolyl group, etc. Substituted thiohendothiazolyl group; aminohenzothiazolyl group; substituted amino such as methylaminohendithiazolyl group, dimethylaminohendithiazolyl group, phenylaminobenzothiazolyl group, diphenylaminohenzothiazolyl group Examples include hengethiazolyl group.
本発明に係わる一般式(r)で表されるジスアゾ化合物
は、従来公知の方法で製造することができる。例えば、
「ジャーナル オブ オーガニック ケミストリー」第
35巻、第2762頁(1970年)に記載の2,7−
ビス(クロロホルミル)−9−フルオレノン(Vl)を
出発物質として、次のような3
4
経路で合成することができる。The disazo compound represented by the general formula (r) according to the present invention can be produced by a conventionally known method. for example,
2,7- described in "Journal of Organic Chemistry" Volume 35, Page 2762 (1970)
It can be synthesized using the following 34 route using bis(chloroformyl)-9-fluorenone (Vl) as a starting material.
(Vl)
Fe/lICff1
DMF
(DMF)
次いで、式(■)で表わされる化合物を常法によりジア
ゾ化し、カプラーCpとアルカリ存在下カップリングさ
せるか、又は、式(■)で表わされる化合物のジアゾニ
ウム塩をボウフッ化水素酸塩或いは亜鉛の塩として一旦
単離した後、適当な溶媒、例えばN、N’−ジメチルホ
ルムアミド、ジメチルスルホキシド等の不活性有機溶媒
中でアルカリの存在下でカプラーとカップリングさせる
ことにより容易に式(’I)の化合物を製造することが
できる。(Vl) Fe/lICff1 DMF (DMF) Next, the compound represented by the formula (■) is diazotized by a conventional method and coupled with the coupler Cp in the presence of an alkali, or the diazonium of the compound represented by the formula (■) is Once the salt is isolated as a hydrofluoride salt or a zinc salt, it is coupled with a coupler in the presence of an alkali in a suitable solvent, such as an inert organic solvent such as N,N'-dimethylformamide or dimethyl sulfoxide. The compound of formula ('I) can be easily produced by the following steps.
本発明で使用できる前記−形成(J)のジスアゾ化合物
の具体例を第1表〜第6表に構造式で示した。Specific examples of the disazo compounds of the above-mentioned -formation (J) that can be used in the present invention are shown in Tables 1 to 6 as structural formulas.
本発明の電子写真用感光体は種々の構造をとることがで
きる。その例を第1〜4図に示した。第1図の感光体は
、導電性支持体(1)上にジスアゾ化合物(3)をバイ
ンダー(4)中に分散させてなる感光層(2a)を設け
たものである。第2図の感光体は、導電性支持体上にジ
スアゾ化合物(3)を電荷輸送物質(5)及びバインダ
ーから成る電荷輸送媒体に分散させて成る感光層(2b
)を設けたものである。第3図及び第4図の感光体はジ
スアゾ化合物(3)を主体とする電荷担体発生層(6)
と、電荷輸送物質とバインダーから成る電荷輸送層(7
)とから成る感光層(2C)又は(2d)をそれぞれ設
けたものである。第1図の場合には、ジスアゾ化合物(
3)は、光減衰に必要な電荷担体の発生及び電荷輸送の
両件用を行なっている。第2図の感光体の場合には、電
荷輸送物質はバインダーと共に電荷輸送媒体(5)を形
成し、一方ジスアゾ化合物(3)は電荷担体発生物質と
して作用する。この電荷輸送媒体(5)はジスアゾ化合
物(3)の如き電荷担体の生成能力は持たないが、ジス
アゾ化合物から発生した電荷担体を受は入れ、これを輸
送する能力を持っている。即ち、第2図の感光体では光
減衰に必要な電荷担体の生成はジスアゾ化合物(3)に
よって行なわれ、一方、電荷担体の輸送は主として電荷
輸送媒体(5)により行なわれる。第3図及び第4図の
感光体の場合には、電荷担体発生層(6)に含まれるジ
スアゾ化合物(3)は電荷担体を発生し、一方、電荷輸
送層(7)は電荷担体の注入を受けその輸送を行なう。The electrophotographic photoreceptor of the present invention can have various structures. Examples are shown in Figures 1-4. The photoreceptor shown in FIG. 1 has a photosensitive layer (2a) formed by dispersing a disazo compound (3) in a binder (4) on a conductive support (1). The photoreceptor shown in FIG. 2 has a photosensitive layer (2b
). The photoreceptor shown in FIGS. 3 and 4 has a charge carrier generation layer (6) mainly composed of a disazo compound (3).
and a charge transport layer (7) consisting of a charge transport substance and a binder.
) and a photosensitive layer (2C) or (2d), respectively. In the case of Figure 1, a disazo compound (
3) is responsible for both the generation of charge carriers necessary for light attenuation and the charge transport. In the case of the photoreceptor of FIG. 2, the charge transport material together with the binder forms the charge transport medium (5), while the disazo compound (3) acts as a charge carrier generating material. Although this charge transport medium (5) does not have the ability to generate charge carriers like the disazo compound (3), it has the ability to accept and transport charge carriers generated from the disazo compound. That is, in the photoreceptor of FIG. 2, the generation of charge carriers necessary for light attenuation is performed by the disazo compound (3), while the transport of charge carriers is mainly performed by the charge transport medium (5). In the case of the photoreceptors shown in Figures 3 and 4, the disazo compound (3) contained in the charge carrier generation layer (6) generates charge carriers, while the charge transport layer (7) injects charge carriers. and transport it.
即ち、光減衰に必要な電荷担体の生成がジスアゾ化合物
で行なわれ、又、電荷担体の輸送が電荷輸送媒体で行な
われると言う作用機構は第2図の感光体の場合と同様で
ある。That is, the mechanism of action is the same as in the case of the photoreceptor shown in FIG. 2, in that charge carriers necessary for light attenuation are generated by a disazo compound, and charge carriers are transported by a charge transport medium.
第1図の感光体はジスアゾ化合物をバインダー溶液中に
分散させ、この分散液を導電性支持体上に塗布、乾燥す
ることによって製造することができる。第2図の感光体
はジスアゾ化合物を電荷輸送物質及びバインダーを溶解
した溶液中に分散せしめ、この分散液を導電性支持体」
二に塗布、乾燥することによって製造することができる
。また、9
0
第3図の感光体は、導電性支持体上にジスアゾ化合物を
真空蒸着するか、或いは、ジスアゾ化合物の微粒子を溶
剤又はバインダー溶液中に分散して得た分散液を塗布、
乾燥し、その上に電荷輸送物質及びバインダーを熔解し
た溶液を塗布、乾燥することにより製造することができ
る。第4図の感光体は電荷輸送物質及びバインダーを熔
解した溶液を導電性支持体上に塗布、乾燥し、その上に
ジスアゾ化合物を真空蒸着するか、或いはジスアゾ化合
物の微粒子を溶剤又はバインダー溶液中に分散して得た
分散液を塗布、乾燥することにより製造することができ
る。The photoreceptor shown in FIG. 1 can be manufactured by dispersing a disazo compound in a binder solution, coating this dispersion on a conductive support, and drying it. The photoreceptor shown in Figure 2 is made by dispersing a disazo compound in a solution containing a charge transporting substance and a binder, and applying this dispersion to a conductive support.
It can be manufactured by coating and drying. 90 The photoreceptor shown in FIG. 3 can be prepared by vacuum-depositing a disazo compound on a conductive support, or by coating a dispersion obtained by dispersing fine particles of a disazo compound in a solvent or binder solution.
It can be manufactured by drying, applying a solution of a charge transporting substance and a binder thereon, and drying. The photoreceptor shown in Fig. 4 can be produced by coating a conductive support with a solution containing a charge transport substance and a binder and drying it, and then vacuum-depositing a disazo compound thereon, or by depositing fine particles of a disazo compound in a solvent or binder solution. It can be manufactured by applying and drying a dispersion obtained by dispersing the liquid into a liquid.
これらの感゛光体の感光層の厚さは、第1図及び第2図
の感光体の場合、3〜50μm、好ましくは5〜20μ
mである。又第3図及び第4図の感光体の場合には、電
荷担体発生層の厚さは5μm以下、好ましくは0.01
〜2μmであり、電荷輸送層の厚さは3〜50μm、好
ましくは5〜20μmである。又、第1図の感光体に於
いて、感光層中のジスアゾ化合物の割合は、感光層に対
して10〜70重景%、重量しくは30〜50重景%で
重量。第2図の感光体に於いては、感光層中のジスアゾ
化合物の割合は1〜50重量%、好ましくは3〜30重
景%重量り、又、電荷輸送物質の割合は10〜90重量
%、好ましくは10〜60重量%である。第3図及び第
4図の感光体における電荷輸送媒体中の電荷輸送物質の
割合は10〜95重量%、好ましくは10〜60重量%
である。The thickness of the photosensitive layer of these photoreceptors is 3 to 50 μm, preferably 5 to 20 μm in the case of the photoreceptors shown in FIGS.
It is m. In the case of the photoreceptor shown in FIGS. 3 and 4, the thickness of the charge carrier generation layer is 5 μm or less, preferably 0.01 μm or less.
~2 μm, and the thickness of the charge transport layer is 3 to 50 μm, preferably 5 to 20 μm. In the photoreceptor shown in FIG. 1, the proportion of the disazo compound in the photosensitive layer is 10 to 70% by weight, or 30 to 50% by weight, based on the photosensitive layer. In the photoreceptor shown in FIG. 2, the proportion of the disazo compound in the photosensitive layer is 1 to 50% by weight, preferably 3 to 30% by weight, and the proportion of the charge transport material is 10 to 90% by weight. , preferably 10 to 60% by weight. The proportion of the charge transport substance in the charge transport medium in the photoreceptor of FIGS. 3 and 4 is 10 to 95% by weight, preferably 10 to 60% by weight.
It is.
本発明の感光体に用いられる導電性支持体としては、例
えば、アルミニウム、銅、亜鉛、ステンレス、クロム、
チタン、ニッケル、モリブデン、バナジウム、インジウ
ム、金、白金等の金属または合金を用いた金属板、金属
ドラム、或いは、導電性ポリマー、酸化インジウム等の
導電性化合物やアルミニウム、パラジウム、金等の金属
又は合金を塗布、蒸着、或いは、ラミネー1− した紙
、プラスチックフィルム等が挙げられる。Examples of the conductive support used in the photoreceptor of the present invention include aluminum, copper, zinc, stainless steel, chromium,
Metal plates or metal drums made of metals or alloys such as titanium, nickel, molybdenum, vanadium, indium, gold, platinum, or conductive polymers, conductive compounds such as indium oxide, metals such as aluminum, palladium, gold, etc. Examples include paper coated with an alloy, vapor-deposited, or laminated with an alloy, a plastic film, and the like.
バインダーとしては、疎水性で、電気絶縁性のフィルム
形成可能な高分子重合体を用いるのが好ましい。この様
な高分子重合体としては、例えば、1
2
ポリカーボネート、ポリエステル、メタクリル樹脂、ア
クリル樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、ポ
リスチレン、ポリビニルアセテート、スチレン−ブタジ
ェン共重合体、塩化ビニリデンアクリロニトリル共重合
体、塩化ビニル−酢酸ビニル共重合体、塩化ビニル−酢
酸ビニル−無水マレイン酸共重合体、シリコン樹脂、シ
リコンアルキッド樹脂、フェノール−ホルムアルデヒド
樹脂、スチレン−アルキッド樹脂、ポリ−N−ビニルカ
ルバゾール、ポリビニルブチラール、ポリビニルフォル
マール、ポリスルホン等が挙ケられるが、これらに限定
されるものではない。As the binder, it is preferable to use a hydrophobic polymer capable of forming an electrically insulating film. Examples of such polymers include 12 polycarbonate, polyester, methacrylic resin, acrylic resin, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, styrene-butadiene copolymer, and vinylidene chloride acrylonitrile copolymer. , vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, silicone resin, silicone alkyd resin, phenol-formaldehyde resin, styrene-alkyd resin, poly-N-vinylcarbazole, polyvinyl butyral, Examples include, but are not limited to, polyvinyl formal and polysulfone.
これらの結着剤は、単独で、或いは2種類以上の混合物
として用いることもできる。These binders can be used alone or as a mixture of two or more.
又、これらのバインダーと共に、可塑剤、増感剤、表面
改質剤等の添加剤を使用することもできる。Additionally, additives such as plasticizers, sensitizers, surface modifiers, etc. can also be used together with these binders.
可塑剤としては、例えば、ビフェニル、塩化ビフェニル
、0−ターフエル、p−ターフェニル、ジブデルフタレ
ート、ジエチレングリコールフタレート、ジオクチルフ
タレート、トリフェニル燐4、酸、メチルナフタレン、
ベンゾフェノン塩素化パラフィン、ポリプロピレン、ポ
リスチレン、各種フルオロ炭化水素等が挙げられる。Examples of the plasticizer include biphenyl, biphenyl chloride, 0-terphenyl, p-terphenyl, dibdelphthalate, diethylene glycol phthalate, dioctyl phthalate, triphenyl phosphorus 4, acid, methylnaphthalene,
Examples include benzophenone, chlorinated paraffin, polypropylene, polystyrene, and various fluorohydrocarbons.
増感剤としては、例えばクロラニル、テトラシアノエチ
レン、メチルバイオレット、ローダミンB1シアニン染
料、メロシアニン染料、ピリリウム染料、チアピリリウ
ム染料等が挙げられる。Examples of the sensitizer include chloranil, tetracyanoethylene, methyl violet, rhodamine B1 cyanine dye, merocyanine dye, pyrylium dye, and thiapyrylium dye.
表面改質剤としては、例えばシリコンオイル、フッソ樹
脂等が挙げられる。Examples of the surface modifier include silicone oil and fluorine resin.
更に本発明に於いては、導電性支持体と感光層との接着
性を向上させたり、導電性支持体から感光層への自由電
荷の注入を阻止する為、導電性支持体と感光層の間に、
必要に応じて接着層或いはバリヤー層を設けることもで
きる。これらの層に用いられる材料としては、前記バイ
ンダーに用いられる高分子化合物のほか、カゼイン、ゼ
ラチン、ポリビニルアルコール、エチルセルロース、ニ
トロセルロース、ポリビニルブチラール、フェノル樹脂
、ポリアミド、カルボキシーメチルセルロ3
4
−ス塩化ビニリデン系ポリマーラテックス、スチレン−
ブタジェン系ポリマーラテックス、ポリウレタン、ゼラ
チン、酸化アルミニウム、酸化スズ、酸化チタン等が挙
げられる。Furthermore, in the present invention, in order to improve the adhesion between the conductive support and the photosensitive layer and to prevent the injection of free charges from the conductive support to the photosensitive layer, Between,
An adhesive layer or barrier layer can also be provided as required. Materials used for these layers include, in addition to the polymer compound used for the binder, casein, gelatin, polyvinyl alcohol, ethyl cellulose, nitrocellulose, polyvinyl butyral, phenolic resin, polyamide, and carboxymethylcellulose 34-suchloride. Vinylidene polymer latex, styrene
Examples include butadiene polymer latex, polyurethane, gelatin, aluminum oxide, tin oxide, titanium oxide, and the like.
又、電荷輸送物質としては、一般に電子を輸送する化合
物と正孔を輸送する化合物との二種類に分類されるが、
本発明の電子写真用感光体には両者とも使用することが
できる。In addition, charge transport materials are generally classified into two types: compounds that transport electrons and compounds that transport holes.
Both can be used in the electrophotographic photoreceptor of the present invention.
電子輸送物質としては、例えば、クロラニル、ブロモア
ニル、テトラシアノエチレン、テトラシアノキノジメタ
ン、2,4.7−ドリニトロー9−フルオレノン、2,
4,5.7−テトラニトロ−9−フルオレノン、9−ジ
シアノメチレン−2,4,7−トリニトロフルオレノン
、9−ジシアノメチレン−24,5,7−テトラニトロ
フルオレノン、2,4,5.7テトラニトロキサントン
、2,4.8−トリニドロチオキサントン、テトラニト
ロカルバゾールクロラニル、2,3−ジクロロ−5,6
−ジシアノベンゾキノン、2,4.7−1−リートロー
9,10−フエナントレンキノン、テトラクロロ無水フ
タール酸等を挙げることができる。Examples of electron transport substances include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4.7-dolinitro-9-fluorenone, 2,
4,5.7-tetranitro-9-fluorenone, 9-dicyanomethylene-2,4,7-trinitrofluorenone, 9-dicyanomethylene-24,5,7-tetranitrofluorenone, 2,4,5.7tetra Nitroxanthone, 2,4.8-trinidrothioxanthone, tetranitrocarbazole chloranil, 2,3-dichloro-5,6
-dicyanobenzoquinone, 2,4,7-1-lytro-9,10-phenanthrenequinone, tetrachlorophthalic anhydride, and the like.
正孔輸送物質としては、低分子化合物では、例エバピレ
ン、N−エチルカルバゾール、N−イソプロピルカルバ
ゾール、N−フェニルカルバソール、或いは、N−メチ
ル−2−フェニルヒドラジノ−3−メチリデン−9−エ
チルカルバゾール、NN−ジフェニルヒドラジノ−3−
メチリデン9−エチルカルバゾール、p−N、N−ジメ
チルアミノベンズアルデヒドジフェニルヒドラゾン、P
NN−ジエチルアミノベンズアルデヒドジフェニルヒド
ラゾン、p−N、N−ジエチルアミノベンズアルデヒド
ジフェニルヒドラゾン等のヒドラゾン類、2,5−ビス
(p−ジエチルアミノフェニル)−1,3,4−オキサ
ジアゾール、1−フェニル−3−(p−ジエチルアミノ
スチリル)−5(p−ジエチルアミノフェニル)ビラプ
リン等の゛ピラゾリン類、トリフェニルアミン、N、N
、N’ 、N’テトラフェニル−1,1′−ビフェニル
−4,4′ジアミン、N、N’−ジフェニル−N、N’
−ビス(3−メチルフェニル) −Ll’ −ビフェ
ニル5
6
4.4′−ジアミン等が挙げられる。又、高分子化合物
としては、例えばポリ−N−ビニルカルバゾール、ハロ
ゲン化ポリ−N−ビニルカルバゾール、ポリビニルピレ
ン、ポリビニルアンスラセン、ポリビニルアクリジン、
ピレン−ボルムアルデヒド樹脂、エチルカルバゾール−
ボルムアルデヒド樹脂、トリフェニルメタンポリマー等
が挙げられる。Examples of the hole transport substance include low molecular compounds such as evapyrene, N-ethylcarbazole, N-isopropylcarbazole, N-phenylcarbazole, or N-methyl-2-phenylhydrazino-3-methylidene-9-ethyl. Carbazole, NN-diphenylhydrazino-3-
Methylidene 9-ethylcarbazole, p-N,N-dimethylaminobenzaldehyde diphenylhydrazone, P
Hydrazones such as NN-diethylaminobenzaldehyde diphenylhydrazone, p-N,N-diethylaminobenzaldehyde diphenylhydrazone, 2,5-bis(p-diethylaminophenyl)-1,3,4-oxadiazole, 1-phenyl-3- Pyrazolines such as (p-diethylaminostyryl)-5(p-diethylaminophenyl) birapurine, triphenylamine, N, N
, N', N'tetraphenyl-1,1'-biphenyl-4,4'diamine, N,N'-diphenyl-N,N'
-Bis(3-methylphenyl)-Ll'-biphenyl564,4'-diamine, and the like. Further, examples of the polymer compound include poly-N-vinylcarbazole, halogenated poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine,
Pyrene-bormaldehyde resin, ethylcarbazole-
Examples include bomaldehyde resin and triphenylmethane polymer.
電荷輸送物質は、ここに記載したものに限定されるもの
ではなく、その使用に際しては単独、或いは2種類以上
混合して用いることができる。The charge transport materials are not limited to those described here, and can be used alone or in combination of two or more kinds.
積層型感光体を塗工によって形成する場合、バインダー
を熔解する溶剤は、バインダーの種類によって異なるが
、下層を溶解しないものの中から選択することが好まし
い。具体的な有機溶剤の例としては、例えば、メタノー
ル、エタノール、nプロパツール等のアルコール類;ア
セトン、メチルエチルケトン、シクロヘキサノン等のケ
トン類;N、N−ジメチルホルムアミド、N、N−ジメ
チルアセトアミド等のアミド類;テトラヒドロフラン、
ジオキサン、メチルセロソルブ等のエーテル類;酢酸メ
チル、酢酸エチル等のエステル類;ジメチルスルホキシ
ド、スルホラン等のスルホキシド及びスルホン類;塩化
メチレン、クロロポル11、四塩化炭素、トリクロロエ
タン等の脂肪族ハロケン化炭化水素;ベンゼン、トルエ
ン、キシレン、モノクロルベンゼン、ジクロルベンゼン
等の芳香族類などが挙げられる。When forming a laminated photoreceptor by coating, the solvent that dissolves the binder varies depending on the type of binder, but it is preferable to select one from among those that do not dissolve the lower layer. Specific examples of organic solvents include alcohols such as methanol, ethanol, and n-propanol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; and amides such as N,N-dimethylformamide and N,N-dimethylacetamide. Class: Tetrahydrofuran,
Ethers such as dioxane and methyl cellosolve; Esters such as methyl acetate and ethyl acetate; Sulfoxides and sulfones such as dimethyl sulfoxide and sulfolane; Aliphatic halosaponified hydrocarbons such as methylene chloride, chloropol 11, carbon tetrachloride, and trichloroethane; Examples include aromatics such as benzene, toluene, xylene, monochlorobenzene, and dichlorobenzene.
塗工法としては、例えば浸漬コーティング法、スプレー
コーティング法、スピナーコーティング法、ビードコー
ティング法、ワイヤーパーコーティング法、ブレードコ
ーティング法、ローラーコーティング法、カーテンコー
ティング法等のコーティング法を用いることができる。As the coating method, coating methods such as dip coating, spray coating, spinner coating, bead coating, wire per coating, blade coating, roller coating, and curtain coating can be used.
以下、実施例により本発明を具体的に説明するが、これ
により本発明が実施例に限定されるものではない。尚、
実施例中「部」とあるのは「重量部」を示す。又、ジス
アゾ化合物のNo、は第1表〜第6表中のNoを意味す
る。EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to the Examples. still,
In the examples, "parts" indicate "parts by weight." Further, No. of the disazo compound means No. in Tables 1 to 6.
7
8
実施例1
ポリエステル樹脂(商品名「バイロン200」東洋紡社
製)10部、No、 1のジスアゾ化合物10部及びテ
トラヒト0フ5フ80部を振動ミル中で粉砕混合し、得
られた分散液をアルミニウム蒸着したポリエステルフィ
ルム上にワイヤーバーで塗布、乾燥し厚さ約10μの感
光層を持った第1図の構造の感光体を得た。次にこの感
光体の感光層面に静電複写紙試験装置Model 5P
−428(川口電機製作所社製)を用いて、ます感光体
を暗所で印加電圧−6kVのコロナ放電により帯電させ
、10秒間暗所に放置し、ついでタングステンランプか
ら、その表面が照度5ルツクスになるように感光層に光
照射を行ない、その表面電位が暗所に10秒間放置後の
表面電位の1/2に減少する迄の時間を測定し、感光度
El/2(ルックス・秒)を求めたところ、El/。−
12,0ルツクス・秒であった。7 8 Example 1 10 parts of polyester resin (trade name "Vylon 200" manufactured by Toyobo Co., Ltd.), 10 parts of disazo compound No. 1, and 80 parts of Tetrahydrof 5F were pulverized and mixed in a vibrating mill, and the resulting dispersion was mixed. The solution was applied with a wire bar onto a polyester film on which aluminum was vapor-deposited, and dried to obtain a photoreceptor having the structure shown in FIG. 1 having a photosensitive layer with a thickness of about 10 μm. Next, an electrostatic copying paper tester Model 5P was applied to the photosensitive layer surface of this photoreceptor.
-428 (manufactured by Kawaguchi Denki Seisakusho Co., Ltd.), the mass photoreceptor was charged in the dark by corona discharge with an applied voltage of -6 kV, left in the dark for 10 seconds, and then the surface was illuminated by a tungsten lamp at an illuminance of 5 lux. The photosensitive layer is irradiated with light so that the surface potential decreases to 1/2 of the surface potential after being left in the dark for 10 seconds. When I asked for it, I got El/. −
It was 12.0 lux·sec.
実施例2
ポリエステル樹脂(実施例1と同製品)3部、2.4.
7− )リートロー9−フル112フ3部、N01のシ
スアヅ化合物0.6部及びテ)・ラヒ1−ロフラン30
部をボールミル中で粉砕混合し、得られた分散液をアル
ミニウムを蒸着したポリエステルフィルム上にワイヤー
バーを用いて塗布乾燥し厚さ約9μの感光層をもった第
2図の構造の感光体を作製した。次にこの感光体の感度
を実施例1に準じて測定したところE、/2=2.8ル
ツクス 秒であった。Example 2 3 parts of polyester resin (same product as Example 1), 2.4.
7-) 3 parts of Leetlow 9-Flu 112, 0.6 part of N01 cis-azu compound and 30 parts of Te) Rahi 1-Rofuran
The resulting dispersion was coated on a polyester film coated with aluminum using a wire bar and dried to form a photoreceptor having the structure shown in Fig. 2 with a photosensitive layer about 9 μm thick. Created. Next, the sensitivity of this photoreceptor was measured according to Example 1 and found to be E,/2=2.8 lux seconds.
実施例3
No、 1のジスアゾ化合物3部をフェノキシ樹脂(商
品名「PKllll」ユニオンカーバイド社製)1部を
ジオル9フフ5部に溶解させた液中で振動ミルを用いて
粉砕混合し、得られた分散液をアルミニウム蒸着ポリエ
ステルフィルム上にワイヤーバーを用いて塗布乾燥し、
厚さ1μの電荷発生層を形成させた。この電荷発生層の
上にp−ジエチルアミノヘンズアルデヒドージフェニル
ヒドラゾン5部、ポリカーボネート樹脂(商品名「パン
ライトL−1250W J奇人化成社製)5部を塩化メ
チレン65部に溶かした溶液をワイヤーバーを用いて塗
9
0
布乾燥し厚さ10μの電荷輸送層を形成せしめ第3図の
構造の感光体を得た。こうして作製した感光体の感度を
実施例1に準して測定したところEl/□−2,4ルツ
クス・秒であった。Example 3 3 parts of the disazo compound No. 1 was pulverized and mixed using a vibrating mill in a solution in which 1 part of phenoxy resin (trade name "PKllll" manufactured by Union Carbide) was dissolved in 5 parts of Diol 9 Fufu. The resulting dispersion was applied onto an aluminum-deposited polyester film using a wire bar and dried.
A charge generation layer having a thickness of 1 μm was formed. A solution of 5 parts of p-diethylaminohenzaldehyde diphenylhydrazone and 5 parts of polycarbonate resin (trade name "Panlite L-1250W, manufactured by J Kijin Kasei Co., Ltd.") dissolved in 65 parts of methylene chloride was placed on top of this charge generation layer using a wire bar. A charge transport layer having a thickness of 10 μm was formed by coating with a 90% cloth and drying to obtain a photoreceptor having the structure shown in FIG. □-2.4 lux·sec.
実施例4〜2O
No、 1のジスアゾ化合物の代りに下記第7表のジス
アゾ化合物を夫々用いた以外は実施例3と同じ方法で第
3図の構造の感光体を作成し、実施例1に準じて感度の
測定を行ない同表に掲げる結果を得た。Examples 4 to 2 A photoreceptor having the structure shown in FIG. 3 was prepared in the same manner as in Example 3, except that the disazo compounds shown in Table 7 below were used in place of the disazo compounds in No. Sensitivity was measured in the same manner and the results listed in the same table were obtained.
第
表
?−
/
/
2
実施例21
電荷輸送物質としてp−ジエチルアミノヘンズアルデヒ
ドーシフェニルヒドラゾンの代りにNエチルカルバソー
ル−3−メチリデン−N−アミノインドリンを用いた以
外は実施例3と同し方法で第3図の構造の感光体を作成
し、実施例1に準じてその感度を測定したところEl/
□−2,フルックス・秒であった。Table? - / / 2 Example 21 The same method as in Example 3 was carried out except that N-ethylcarbasol-3-methylidene-N-aminoindoline was used instead of p-diethylaminohenzaldehydecyphenylhydrazone as the charge transport material. A photoreceptor having the structure shown in Figure 3 was prepared and its sensitivity was measured according to Example 1.
□-2, flux seconds.
実施例22〜4O
No、 1のジスアゾ化合物の代りに下記第8表のジス
アゾ化合物を夫々用い、且つ電荷輸送物質としてp−ジ
エチルアミノヘンズアルデヒドージフェニルヒドラプン
の代りにN−エチルカルバゾール3−メチリデン−N−
アミノインドリンを用いた以外は実施例3と同じ方法で
第3図の構造の感光体を作成し、実施例1に準じて感度
の測定を行ない第8表に掲げる結果を得た。Examples 22 to 4O In place of the disazo compound in No. 1, the disazo compounds listed in Table 8 below were used, and as the charge transport substance, N-ethylcarbazole 3-methylidene was used in place of p-diethylaminohenzaldehyde diphenylhydrapune. N-
A photoreceptor having the structure shown in FIG. 3 was prepared in the same manner as in Example 3 except that aminoindoline was used, and the sensitivity was measured in accordance with Example 1 to obtain the results listed in Table 8.
3
実施例41
電荷輸送物質としてp−ジエチルアミノベンズアルデヒ
ド−ジフェニルヒドラゾンの代りにNエチルカルバゾー
ル−3−メチリデン−N−アミノテトラヒドロキノリン
を用いた以外は実施例3と同し方法で第3図の構造の感
光体を作成し、実施例1に準して感度を測定したところ
El/□−2,8ルツクス・秒であった。3 Example 41 The structure shown in FIG. 3 was prepared in the same manner as in Example 3 except that N-ethylcarbazole-3-methylidene-N-aminotetrahydroquinoline was used instead of p-diethylaminobenzaldehyde-diphenylhydrazone as the charge transport material. A photoreceptor was prepared, and the sensitivity was measured according to Example 1 and found to be El/□-2.8 lux·sec.
実施例42〜6O
No、 1のジスアゾ化合物の代りに下記第9表のジス
アゾ化合物を夫々用い、且つ電荷輸送物質としてp−ジ
エチルアミノヘンズアルデヒドージフェニルヒドラゾン
の代りにN−エチルカルバゾール3−メチリデン−N−
アミノテトラヒドロキノリンを用いた以外は実施例3と
同じ方法で第3図の構造の感光体を作成し、実施例1に
準じて感度の測定を行ない、同表に掲げる結果を得た。Examples 42 to 6O The disazo compounds shown in Table 9 below were used in place of the disazo compound in No. 1, and N-ethylcarbazole 3-methylidene-N was used in place of p-diethylaminohenzaldehyde diphenylhydrazone as the charge transport substance. −
A photoreceptor having the structure shown in FIG. 3 was prepared in the same manner as in Example 3, except that aminotetrahydroquinoline was used, and the sensitivity was measured in accordance with Example 1, and the results listed in the table were obtained.
5
実施例61
ポリカーボネート樹脂(実施例3と同製品)3部、p−
ジエチルアミノヘンスアルデヒドージフェニルヒドラゾ
ン3部をテトラヒドロフラン35部に溶かした溶液をア
ルミニウムを蒸着したポリエステルフィルム上にワイヤ
ーパーを用いて塗布乾燥し厚さ約10μの電荷輸送層を
形成せしめた。5 Example 61 3 parts of polycarbonate resin (same product as Example 3), p-
A solution of 3 parts of diethylaminohensaldehyde diphenylhydrazone dissolved in 35 parts of tetrahydrofuran was applied onto a polyester film on which aluminum had been deposited using a wire spar and dried to form a charge transport layer with a thickness of about 10 μm.
次に実施例3において電荷発生層の形成に用いた塗料を
上記電荷輸送層の」二にワイヤーバーを用いて塗布乾燥
し厚さ約0.8μの電荷発生層を形成せしめ第4図の構
造の感光体を得た。こうして作製した感光体の感度を印
加電圧+6にνのコロナ放電を行ない実施例1に準じて
測定したところEl/□−2,6ルツクス・秒であった
。Next, the paint used to form the charge generation layer in Example 3 was applied to the second part of the charge transport layer using a wire bar and dried to form a charge generation layer with a thickness of about 0.8μ, and the structure shown in FIG. A photoreceptor was obtained. The sensitivity of the thus prepared photoreceptor was measured according to Example 1 by applying a corona discharge of ν to an applied voltage of +6 and found to be El/□-2.6 lux·sec.
本発明の電子写真用感光体は、耐久性に研れ、高感度で
あるので、ppc複写機等に広く利用することができる
。The electrophotographic photoreceptor of the present invention has good durability and high sensitivity, so it can be widely used in PPC copying machines and the like.
第1〜4図は、本発明に係わる電子写真用感光体の拡大
部分断面図である。
■・・・導電性支持体、2a、2b、2c 2d−感
光層、3・・・ジスアゾ化合物、4・・・バインダー、
5・・・電荷輸送物質、6・・・電荷担体発生層、7・
・・電荷輸送層。1 to 4 are enlarged partial cross-sectional views of the electrophotographic photoreceptor according to the present invention. ■... Conductive support, 2a, 2b, 2c 2d-photosensitive layer, 3... Disazo compound, 4... Binder,
5... Charge transport material, 6... Charge carrier generation layer, 7.
...Charge transport layer.
Claims (1)
真用感光体。 2、Cpが一般式(II) ▲数式、化学式、表等があります▼ 一般式(III) ▲数式、化学式、表等があります▼ 一般式(IV) ▲数式、化学式、表等があります▼ 又は一般式(V) ▲数式、化学式、表等があります▼ (式中、Xは、置換基を有していてもよい炭化水素環又
は複素環を表わし、Yは、 ▲数式、化学式、表等があります▼又は▲数式、化学式
、表等があります▼を表わし、R^1、R^2及びR^
3は各々独立的に水素原子、置換基を有していても良い
炭化水素基又は複素環基を表わし、R^1及びR^2は
互いに環を形成していてもよい。) で表わされるカプラー残基である請求項1記載の電子写
真用感光体。[Claims] 1. Electrophotography characterized by containing a compound represented by the general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, Cp represents a coupler residue.) Photoreceptor for use. 2. Cp is general formula (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ General formula (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ General formula (IV) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or General formula (V) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X represents a hydrocarbon ring or heterocycle that may have a substituent, and Y is ▲Mathematical formulas, chemical formulas, tables, etc. There are ▼ or ▲ there are mathematical formulas, chemical formulas, tables, etc. ▼, which represents R^1, R^2 and R^
3 each independently represents a hydrogen atom, a hydrocarbon group or a heterocyclic group which may have a substituent, and R^1 and R^2 may mutually form a ring. ) The electrophotographic photoreceptor according to claim 1, which is a coupler residue represented by the following formula.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14414589A JPH0310255A (en) | 1989-06-08 | 1989-06-08 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14414589A JPH0310255A (en) | 1989-06-08 | 1989-06-08 | Electrophotographic sensitive body |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0310255A true JPH0310255A (en) | 1991-01-17 |
Family
ID=15355271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14414589A Pending JPH0310255A (en) | 1989-06-08 | 1989-06-08 | Electrophotographic sensitive body |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0310255A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10143450B2 (en) | 2012-11-02 | 2018-12-04 | Koninklijke Philips N.V. | System with photonic biopsy device for obtaining pathological information |
US10390805B2 (en) | 2012-06-26 | 2019-08-27 | Koninklijke Philips N.V. | Biopsy needle with large fiber distance at the tip |
-
1989
- 1989-06-08 JP JP14414589A patent/JPH0310255A/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10390805B2 (en) | 2012-06-26 | 2019-08-27 | Koninklijke Philips N.V. | Biopsy needle with large fiber distance at the tip |
US10143450B2 (en) | 2012-11-02 | 2018-12-04 | Koninklijke Philips N.V. | System with photonic biopsy device for obtaining pathological information |
US11406367B2 (en) | 2012-11-02 | 2022-08-09 | Koninklijke Philips N.V. | System with photonic biopsy device for obtaining pathological information |
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