JPS63151952A - Electrophotographic sensitive body - Google Patents
Electrophotographic sensitive bodyInfo
- Publication number
- JPS63151952A JPS63151952A JP29877686A JP29877686A JPS63151952A JP S63151952 A JPS63151952 A JP S63151952A JP 29877686 A JP29877686 A JP 29877686A JP 29877686 A JP29877686 A JP 29877686A JP S63151952 A JPS63151952 A JP S63151952A
- Authority
- JP
- Japan
- Prior art keywords
- group
- optionally substituted
- substituted phenyl
- groups
- sensitive body
- 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
- -1 aromatic ester compound Chemical class 0.000 claims abstract description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 108091008695 photoreceptors Proteins 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 15
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 10
- 230000036211 photosensitivity Effects 0.000 abstract description 10
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical class CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 39
- 238000000034 method Methods 0.000 description 21
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 8
- 239000000975 dye Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 125000004986 diarylamino group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- 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 2
- 235000021240 caseins Nutrition 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical class C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000007761 roller coating Methods 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 238000007740 vapor deposition Methods 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
- FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-UHFFFAOYSA-N 0.000 description 1
- HEZIOZBMPKPOER-UHFFFAOYSA-N 2,3-dimethoxyaniline Chemical group COC1=CC=CC(N)=C1OC HEZIOZBMPKPOER-UHFFFAOYSA-N 0.000 description 1
- QIJXCJUUAAZCOQ-UHFFFAOYSA-N 2-ethenyl-1-phenylanthracene Chemical compound C=CC1=CC=C2C=C3C=CC=CC3=CC2=C1C1=CC=CC=C1 QIJXCJUUAAZCOQ-UHFFFAOYSA-N 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
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- MYHNMZPERVYEKS-UHFFFAOYSA-N 4-(1,3-benzoxazol-2-yl)-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NC2=CC=CC=C2O1 MYHNMZPERVYEKS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FAPXNOXKLZJBMT-UHFFFAOYSA-N 4-[5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazol-2-yl]-n,n-dimethylaniline Chemical class C1=CC(N(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(C)C)O1 FAPXNOXKLZJBMT-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical group NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical group OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 description 1
- SDSADASZTPUXMK-UHFFFAOYSA-N N-(benzylideneamino)-2-(dimethylamino)benzamide Chemical compound CN(C)C1=C(C(=O)NN=CC2=CC=CC=C2)C=CC=C1 SDSADASZTPUXMK-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910001370 Se alloy Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- TXVHTIQJNYSSKO-UHFFFAOYSA-N benzo[e]pyrene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 125000005578 chrysene group Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 125000005583 coronene group Chemical group 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000007606 doctor blade method Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- GPTJOKIAEFMJDJ-UHFFFAOYSA-N n,n-diethyl-4-(1-ethyl-6-methylbenzimidazol-2-yl)aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NC2=CC=C(C)C=C2N1CC GPTJOKIAEFMJDJ-UHFFFAOYSA-N 0.000 description 1
- MHIJXEIWFUZDBF-UHFFFAOYSA-N n-[[4-(dimethylamino)phenyl]methylideneamino]-2-methylbenzamide Chemical compound C1=CC(N(C)C)=CC=C1C=NNC(=O)C1=CC=CC=C1C MHIJXEIWFUZDBF-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- CJABVFCUCRAVOK-UHFFFAOYSA-N pyrene-1,2-dione Chemical class C1=C2C(=O)C(=O)C=C(C=C3)C2=C2C3=CC=CC2=C1 CJABVFCUCRAVOK-UHFFFAOYSA-N 0.000 description 1
- FMKFBRKHHLWKDB-UHFFFAOYSA-N rubicene Chemical group C12=CC=CC=C2C2=CC=CC3=C2C1=C1C=CC=C2C4=CC=CC=C4C3=C21 FMKFBRKHHLWKDB-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0503—Inert supplements
- G03G5/051—Organic non-macromolecular compounds
- G03G5/0517—Organic non-macromolecular compounds comprising one or more cyclic groups consisting of carbon-atoms only
Abstract
Description
【発明の詳細な説明】
〔発明の目的〕
（産業上の利用分野）
本発明は、カールソン方式に用いて有効な電子写真感光
体に関する。DETAILED DESCRIPTION OF THE INVENTION [Object of the Invention] (Industrial Application Field) The present invention relates to an electrophotographic photoreceptor that is effective for use in the Carlson method.
（従来の技術）
電子写真感光体の光導電プロセスは、光電荷発生プロセ
ス及び電荷輸送プロセスから成る。従来電子写真感光体
は上記の２つのプロセスを一個の物質でおこなう方法と
それぞれ別個の物質でおこなう方法とが知られている。(Prior Art) The photoconductive process of electrophotographic photoreceptors consists of a photocharge generation process and a charge transport process. Conventionally, for electrophotographic photoreceptors, two methods are known: one in which the above two processes are carried out using one substance, and the other in which the two processes are carried out using separate substances.
上記した２つの方法のうち、それぞれのプロセスを別個
の物質でおこなう方法は、感光体に用いて材料の選択範
囲が広がり、得られた感光体の感度及び受容電位等の電
子写真特性がすぐれ、かつ感光体製造に際し、被膜物性
等の優れた感光体を製造できるという利点を有する。Of the two methods described above, the method in which each process is performed using separate substances expands the range of materials that can be selected for the photoreceptor, and the resulting photoreceptor has excellent electrophotographic properties such as sensitivity and acceptance potential. In addition, it has the advantage that a photoreceptor with excellent coating properties can be produced when manufacturing a photoreceptor.
従来、この方法を用いた感光体としては、導電性支持体
上に電荷発生物質として無定形セレンから成る電荷発生
層を設け、その上にポリビニルカルバゾールからなる電
荷輸送層を設けた感光体がよく知られている。Conventionally, a photoreceptor using this method is a photoreceptor in which a charge generation layer made of amorphous selenium as a charge generation substance is provided on a conductive support, and a charge transport layer made of polyvinyl carbazole is provided on top of the charge generation layer. Are known.
しかし、電荷輸送層に用いるポリビニルカルバゾールは
可撓性に欠けるため形成された層の被膜は固く、もろく
、かつひび割れや膜はがれ等の現象を起こしやすく、感
光体としての耐久性が劣るという欠点がある。そこでポ
リビニルカルバゾールの可撓性を増すために可塑剤と共
に用いる方法が提案されている。しかしこの方法は、電
荷輸送層の残留電荷が増加し１画像にカブリを生じせし
める等の電子写真特性が低下するという大きな欠点を有
している。However, the polyvinyl carbazole used for the charge transport layer lacks flexibility, so the formed layer is hard and brittle, and is prone to cracking and peeling, resulting in poor durability as a photoreceptor. be. Therefore, in order to increase the flexibility of polyvinylcarbazole, a method of using it together with a plasticizer has been proposed. However, this method has a major drawback in that the residual charge in the charge transport layer increases and the electrophotographic properties deteriorate, such as fogging in one image.
また、低分子量の有機化合物を用いることが提案されて
いる。がしかし例えば２．５−ビス（Ｐ−ジエチルアミ
ノフェニル）−１，３，４−オキサゾールのように、感
度的に十分ではなく、又繰返し露光帯電を行なった時に
表面電位の変動、特に帯電能の低下、残留電位の上昇を
起こすものが多い。It has also been proposed to use low molecular weight organic compounds. However, for example, 2,5-bis(P-diethylaminophenyl)-1,3,4-oxazole is not sensitive enough, and when repeated exposure charging is performed, the surface potential changes, especially the charging ability. There are many things that cause a decrease in residual potential and an increase in residual potential.
（発明が解決しようとする問題点） 上記のように従来の電子写真感光体は、可撓性。(Problem that the invention attempts to solve) As mentioned above, conventional electrophotographic photoreceptors are flexible.
光感度、及び繰り返し使用による特性低下に問題点を有
している。It has problems with photosensitivity and deterioration of characteristics due to repeated use.
本発明は、この従来の電子写真感光体の欠点を解消し、
柔軟性に優れ光感度帯電特性、残留電位特性に優れてい
ると共に、繰り返し使用による諸特性の変化が小さい電
子写真感光体の提供を目的とする。The present invention eliminates the drawbacks of the conventional electrophotographic photoreceptor,
An object of the present invention is to provide an electrophotographic photoreceptor which is excellent in flexibility, photosensitivity and charging characteristics, and residual potential characteristics, and whose various characteristics change little due to repeated use.
（問題点を解決するための手段及び作用）本発明は導電
性支持体上に電荷発生物質と電荷輸送物質を含有する感
光層を設けて成る電子写真感光体において該感光層が下
記一般式（１）及び／又は（ＩＩ）で示される芳香族エ
ステル化合物を少なくとも一種含有することを特徴とす
る電子写真感光体である
Ｒ、−Ｃ−０−Ｒ，（１）
■
式中Ｒ１〜Ｒ４は置換されてもよいフェニル基を示し同
じであっても異なってもよい
Ｒ５は置換されてもよいフェニル基又は−Ａ−Ｘ−Ｂ−
で示され
Ａ、Ｂは置換されてもよいフェニル基。(Means and effects for solving the problems) The present invention provides an electrophotographic photoreceptor comprising a photosensitive layer containing a charge generating substance and a charge transporting substance on a conductive support, in which the photosensitive layer has the following general formula ( R, -C-0-R, (1), which is an electrophotographic photoreceptor characterized by containing at least one aromatic ester compound represented by 1) and/or (II), where R1 to R4 are Represents an optionally substituted phenyl group, and R5, which may be the same or different, represents an optionally substituted phenyl group or -A-X-B-
A and B are phenyl groups that may be substituted.
Ｘは２価のアルキル基又はシクロアルキル基。X is a divalent alkyl group or a cycloalkyl group.
アラルキル基、アリール基である
本発明は、導電性支持体の上に単一の光導電層を設けた
単層型感光体、電荷発生層と電荷輸送層とからなる機能
分離型感光体などいずれのタイプの電子写真感光体にも
適用することができる。特に機能分離型単層及び積層型
感光体に適しており、電荷輸送物質と共に用いることに
より効力を発揮するものである。以下機能分離型感光体
を例にとり本発明の詳細な説明する。The present invention, which is an aralkyl group or an aryl group, can be applied to a single-layer type photoreceptor in which a single photoconductive layer is provided on a conductive support, a functionally separated type photoreceptor consisting of a charge generation layer and a charge transport layer, etc. It can also be applied to the type of electrophotographic photoreceptor. It is particularly suitable for functionally separated single-layer and laminated photoreceptors, and is effective when used together with a charge transport material. The present invention will be described in detail below using a functionally separated photoreceptor as an example.
本発明の電子写真感光体は、少なくとも導電性支持体と
電荷発生層と電荷輸送層とから成る３層構造体であり、
導電性支持体の上に電荷発生層又は電荷輸送層が順次積
層されている。導電支持体への電荷発生層と電荷輸送層
の積層順序は格別限定されるものではないが、感光体の
物理的強度を高めるという点からすると、導電性支持体
と電荷輸送層とをこの順序で積層した構造のものが好ま
しい。The electrophotographic photoreceptor of the present invention is a three-layer structure consisting of at least a conductive support, a charge generation layer, and a charge transport layer,
A charge generation layer or a charge transport layer is sequentially laminated on a conductive support. Although the order in which the charge generation layer and the charge transport layer are stacked on the conductive support is not particularly limited, from the viewpoint of increasing the physical strength of the photoreceptor, it is preferable to stack the conductive support and the charge transport layer in this order. A laminated structure is preferable.
本発明において使用される導電性支持体は１通常、電子
写真感光体の導電性支持体として使用されているもので
あれば何であってもよく、格別制限されるものではない
。このような支持体としては、例えば、真ちゅう、アル
ミニウム、金、銀等の金属材料；前記金属の表面がプラ
スチックの薄膜で被覆されたちの；金属被Ｎ紙、金属被
覆プラスチックシート或はヨウ化アルミニウム、ヨウ化
銅、酸化クロム又は酸化スズ等の導電層で被覆されたガ
ラス等が上げられる。これらは、適当な厚さ、硬さ及び
屈曲性を有する円筒状シート薄板として使用され、支持
体自身が導電性を有するか、又はその表面が導電性を有
し、取扱いに際して十分な強度を有しているものである
ことが好ましい。The conductive support used in the present invention is not particularly limited, and may be any support that is normally used as a conductive support for electrophotographic photoreceptors. Such supports include, for example, metal materials such as brass, aluminum, gold, and silver; metal surfaces coated with a thin film of plastic; metal-covered paper, metal-covered plastic sheets, or aluminum iodide. , glass coated with a conductive layer such as copper iodide, chromium oxide or tin oxide. These are used as thin cylindrical sheets with appropriate thickness, hardness, and flexibility, and either the support itself is conductive or its surface is conductive, and has sufficient strength for handling. It is preferable that the
このような導電性支持体の上に、後述する電荷発生層又
は電荷輸送層を形成する。A charge generation layer or a charge transport layer, which will be described later, is formed on such a conductive support.
電荷発生層を構成する物質としては、光を吸収して高い
効率で電荷（キャリア）を発生する電荷発生物質であれ
ば、どのような物質であってもよい。The charge generation layer may be made of any charge generation material as long as it absorbs light and generates charges (carriers) with high efficiency.
このような電荷発生物質としては、例えば、セレン及び
セレン合金： ＣｄＳ、ＣｄＳｅ、Ｃｄ５５ｓ、ＺｎＯ
及びＺｎＳ等の無機光導電体；金属フタロシアニン及び
無金属フタロシアニン等のフタロシアニン顔料；モノア
ゾ色素及びジスアゾ色素等のアゾ系色素；ペニレン酸無
水物及びペニレン酸イミド等のペニレン系顔料；インジ
ゴイド染料；キナクリドン顔料；アントラキノン類及び
ピレンキノン類等の多環キノン類；シアニン色素；キサ
ンチン染料；ポリ−Ｎ−ビニルカルバゾール等の電子供
与性物質とトリニトロフルオレノン等の電子受容性物質
とから成る電荷移動錯体：並びにピリリウム塩染料とポ
リカーボネート樹脂とから成る共晶錯体等が挙げられる
。Examples of such charge generating substances include selenium and selenium alloys: CdS, CdSe, Cd55s, ZnO
and inorganic photoconductors such as ZnS; phthalocyanine pigments such as metal phthalocyanine and metal-free phthalocyanine; azo dyes such as monoazo dyes and disazo dyes; penylene pigments such as penylene acid anhydride and penylene acid imide; indigoid dyes; quinacridone pigments ; polycyclic quinones such as anthraquinones and pyrenequinones; cyanine dyes; xanthine dyes; charge transfer complexes consisting of electron donating substances such as poly-N-vinylcarbazole and electron accepting substances such as trinitrofluorenone; Examples include eutectic complexes consisting of salt dyes and polycarbonate resins.
電荷発生層の形成方法としては、使用する電荷発生物質
の種類によっても異なってくるが、例えば、スピンコー
ティング法、引−ヒげ法、ローラ塗布法、ドクターブレ
ード塗布法など各種の塗布法、真空蒸着法、スパッタリ
ング法、グロー放電を利用した倒えばプラズマＣＶＤ法
から適宜に選択して適用することができる。Methods for forming the charge generation layer vary depending on the type of charge generation substance used, but include various coating methods such as spin coating, drag coating, roller coating, doctor blade coating, vacuum coating, etc. The method can be appropriately selected from vapor deposition method, sputtering method, and plasma CVD method using glow discharge.
電荷発生層との間に接着層を形成してもよい。An adhesive layer may be formed between the charge generation layer and the charge generation layer.
接着層の物質としてはカゼイン等従来よく使用されてい
る物質を適用することができ、その厚みは０．１〜１０
−９好ましくは０．５〜２−程度がよい。As the material for the adhesive layer, conventionally commonly used materials such as casein can be used, and the thickness thereof is 0.1 to 10.
-9 Preferably about 0.5 to 2-.
なお導電性支持体上に電荷発生層を形成する際に必要に
よっては、導電性支持体と電荷発生層との間に接着層を
形成してもよい。接着層には、カゼイン等従来よりよく
使用されている物質を用いることができ、その厚みは、
０．１−１０．、好ましくは０．５〜２１程度がよい。Note that when forming the charge generation layer on the conductive support, an adhesive layer may be formed between the conductive support and the charge generation layer, if necessary. For the adhesive layer, a conventionally commonly used substance such as casein can be used, and its thickness is as follows:
0.1-10. , preferably about 0.5 to 21.
本発明で用いろ電荷輸送層を構成する電荷輸送物質とし
ては、電荷発生層より効率良くキャリヤを受は取り、か
つキャリヤを効率良く輸送させろ物質であれば、どのよ
うな物質であってもよい。As the charge transport material constituting the charge transport layer used in the present invention, any material may be used as long as it can receive and take carriers more efficiently than the charge generation layer and transport carriers more efficiently. .
このよような電荷輸送物質としては、例えば次のような
ものがあげられる。すなわち、アントラセン、フェナン
トレン、ピレン、コロネンなどの縮合多環式化合物；ポ
リビニルピレン、ポリビニルアントラセン、ポリ−９−
ビニルフェニルアントラセンなどの縮合多環式化合物の
高分子化物；ジフェニルアミン、ジナフチルアミン、ト
リフェニルアミン、４，４′−ビス−（Ｎ、Ｎ−ジエチ
ルアミノコテトラフェニルメタンなどの芳香族アミン化
合物；４−ジメチルアミノベンジリデンベンズヒドラジ
ド、４−ジメチルアミノベンジリデン−２−メチル安息
香酸ヒドラジドなどのアシルヒドラジド誘導体；２−［
４−ジメチルアミノフェニル〕−５−フェニル−オキサ
ゾール、２−［４’−ジエチルアミノフェニル〕−ベン
ズオキサゾールなどのオキサゾール誘導体；４−（４’
−ジメチルアミノフェニル〕−５−フェニル−イミダ
ゾール、１−エチル−２−［４’ −ジエチルアミノフ
ェニル〕−６−メチル−ベンズイミダゾールなどのイミ
ダゾール誘導体：２−［４’ −ジエチルアミノフェニ
ルコーチアゾール、２−（４’ −ジメチルアミノフェ
ニル〕−ベンズチアゾールなどのチアゾール誘導体；
ｌ、３．５−トリフェニルピラゾリン、１−フェニル−
３−［４’ −ジエチルアミノスチリル〕−４−メチル
−５−［４’−ジエチルアミノフェニル〕−ピラゾリン
などのピラゾリン誘導体；４．５−ジフェニルイミダシ
ロンなどのイミダシロン誘導体；４，５−ジフェニルイ
ミダゾチオンなどのイミダゾチオン誘導体；２．５−ビ
ス−〔４′−ジメチルアミノフェニル〕−１，３，４−
オキサジアゾール、２− （４’ −ジメチルアミノフ
ェニル）−５−（４’−アミノ−３′−クロルフェニル
）−１，３，／Ｉ−オキサジアゾールなどのオキサジア
ゾール誘導体；２゜５−ビス−〔４′−ジメチルアミノ
フェニル〕−１，３，４−チアジアゾールなどのチアジ
アゾール誘導体；２，５−ビス−〔４′−ジメチルアミ
ノフェニル）−１，３，４−）−リアゾールなどのトリ
アゾール誘導体；カルバゾール、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
バゾール、ペンズカルバゾールなどのカルバゾール誘導
体；ポリ−Ｎ−ビニルカルバゾール、ニトロ化ポリ−Ｎ
−ビニルカルバゾール、塩素化ポリ−Ｎ−ビニルカルバ
ゾール、臭素化ポリ−Ｎ−ビニルカルバゾールなどのポ
リーＮ−ビニルカルバゾール誘芯体、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、Ｎ−エチ
ル−３−カルボキシアルデヒド−メチルフェニルヒドラ
ゾンなどのヒドラゾン化合物である。この電荷輸送物質
と共に用いる一般式（り。Examples of such charge transport materials include the following. That is, fused polycyclic compounds such as anthracene, phenanthrene, pyrene, and coronene; polyvinylpyrene, polyvinylanthracene, poly-9-
Polymerized polycyclic compounds such as vinylphenylanthracene; aromatic amine compounds such as diphenylamine, dinaphthylamine, triphenylamine, 4,4'-bis-(N,N-diethylaminocotetraphenylmethane); 4- Acyl hydrazide derivatives such as dimethylaminobenzylidene benzhydrazide, 4-dimethylaminobenzylidene-2-methylbenzoic acid hydrazide; 2-[
Oxazole derivatives such as 4-dimethylaminophenyl]-5-phenyl-oxazole, 2-[4'-diethylaminophenyl]-benzoxazole;4-(4'
Imidazole derivatives such as -dimethylaminophenyl]-5-phenyl-imidazole, 1-ethyl-2-[4'-diethylaminophenyl]-6-methyl-benzimidazole: 2-[4'-diethylaminophenylcortiazole, 2- Thiazole derivatives such as (4'-dimethylaminophenyl]-benzthiazole;
l, 3.5-triphenylpyrazoline, 1-phenyl-
Pyrazoline derivatives such as 3-[4'-diethylaminostyryl]-4-methyl-5-[4'-diethylaminophenyl]-pyrazoline; imidasilone derivatives such as 4,5-diphenylimidasilone; 4,5-diphenylimidazothione imidazothione derivatives such as; 2,5-bis-[4'-dimethylaminophenyl]-1,3,4-
Oxadiazole derivatives such as oxadiazole, 2-(4'-dimethylaminophenyl)-5-(4'-amino-3'-chlorophenyl)-1,3,/I-oxadiazole; 2゜5 -thiadiazole derivatives such as -bis-[4'-dimethylaminophenyl]-1,3,4-thiadiazole; Triazole derivatives; carbazole derivatives such as carbazole, N-ethylcarbazole, N-isopropylcarbazole, N-phenylcarbazole, penzcarbazole; poly-N-vinylcarbazole, nitrated poly-N
- Poly N-vinylcarbazole derivatives such as vinylcarbazole, chlorinated poly-N-vinylcarbazole, brominated poly-N-vinylcarbazole, P-diethylaminobenzaldehyde-diphenylhydrazone, N-ethyl-3-carboxaldehyde-methyl Hydrazone compounds such as phenylhydrazone. General formula (RI) used with this charge transport material.
（■）で示される芳香族エステル化合物の置換基として
は、例えば、メチル基、エチル基、プロピル基等のアル
キル基；メチレン基、エチレン基、プロピレン基等のア
ルキレン基；メトキシ基、エトキシ基等のアルコキシ基
；フェノキシ基等のアリールオキシ基；塩素、臭素等の
ハロゲン原子；ジメチルアミノ基、ジエチルアミノ基、
エチルブチルアミノ基等のジアルキルアミノ基；ジフェ
ニルアミノ基等のジアリールアミノ基；エチルフェニル
アミノ基等のアルキルアリールアミノ基；メチルチオ基
、エチルチオ基等のアルキルチオ基；ニトロ基ニジアノ
基；アミノ基；ヒドロキシル基：メチルエステル基、エ
チルエステル基、ブエニルエステル基等のエステル基；
フェニルアミド基。Examples of the substituents of the aromatic ester compound represented by (■) include alkyl groups such as methyl, ethyl, and propyl; alkylene groups such as methylene, ethylene, and propylene; methoxy, and ethoxy groups; alkoxy groups; aryloxy groups such as phenoxy groups; halogen atoms such as chlorine and bromine; dimethylamino groups, diethylamino groups,
Dialkylamino groups such as ethylbutylamino group; Diarylamino groups such as diphenylamino group; Alkylarylamino groups such as ethylphenylamino group; Alkylthio groups such as methylthio group and ethylthio group; Nitro group, Nidiano group; Amino group; Hydroxyl group : Ester groups such as methyl ester group, ethyl ester group, butenyl ester group;
Phenylamide group.
ジメトキシフェニルアミド基等のアミド基；ジ置換アミ
ノ基（例えば、ジメチルアミノ基、ジエチルアミノ基、
ジブチルアミノ基、メチルエチルアミノ基、メチルブチ
ルアミノ基、シアミルアミノ基等のジアルキルアミノ基
；ジベンジルアミノ基。Amide groups such as dimethoxyphenylamide groups; di-substituted amino groups (e.g. dimethylamino groups, diethylamino groups,
Dialkylamino groups such as dibutylamino group, methylethylamino group, methylbutylamino group, cyamylamino group; dibenzylamino group.
ドフェネチルアミノ基等のジアラルキルアミノ基；ジフ
ェニルアミノ基、ジトリルアミノ基、ジキシリルアミノ
基等のジアリールアミノ基）やアルコキシ基（例えば、
メトキシ基、エトキシ基、プロポキシ基、ブトキシ基）
やアリールオキシ基（例えばフェノキシ基、ナフトキシ
基）やアルキル基やニトロ基やシアノ基やヒドロキシ基
やアセチル基やハロゲンにより置換されてもよいフェニ
ル基。dialkylamino groups such as dophenethylamino group; diarylamino groups such as diphenylamino group, ditolylamino group, dixylylamino group) and alkoxy groups (e.g.
methoxy group, ethoxy group, propoxy group, butoxy group)
, an aryloxy group (for example, a phenoxy group, a naphthoxy group), an alkyl group, a nitro group, a cyano group, a hydroxy group, an acetyl group, or a phenyl group which may be substituted with a halogen.
ナフチル基、アントラセン基、フェナントレン基、テト
ラリン基、アズレン基、ビフェニレン基、アセナフチレ
ン基、アセナフテン基、フルオレン基、フルオランテン
基、トリフェニレン基、ピレン基、クリセン基、ナフタ
セン基、ビセン基、ペリレン基、ベンゾピレン基、ルビ
セン基、コロネン基、オバレン基等のアリール基；ジ置
換アミノ基（例えば、ジメチルアミノ基、ジエチルアミ
ノ基、ジブチルアミノ基、メチルエチメアミノ基、メチ
ルブチルアミノ基、シアミルアミノ基等のジアルキルア
ミノ基；ジベンジルアミノ基、ジアリールアミノ基等の
ジアラルキルアミノ基；ジフェニルアミノ基、ジトリル
アミノ基、ジキシリルアミノ基等のジアリールアミノ基
）やアルコキシ基（例えば、メトキシ基、エトキシ基、
プロポキシ基。Naphthyl group, anthracene group, phenanthrene group, tetralin group, azulene group, biphenylene group, acenaphthylene group, acenaphthene group, fluorene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, bicene group, perylene group, benzopyrene group , rubicene group, coronene group, obalene group, etc.; di-substituted amino groups (for example, di-substituted amino groups (e.g., dimethylamino group, diethylamino group, dibutylamino group, methylethimeamino group, methylbutylamino group, cyamyl amino group, etc.); ; dialkylamino groups such as dibenzylamino group and diarylamino group; diarylamino groups such as diphenylamino group, ditolylamino group and dixylylamino group) and alkoxy groups (e.g. methoxy group, ethoxy group,
Propoxy group.
ブトキシ基）やアリールオキシ基（例えば、フェノキシ
基、ナフトキシ基）やアルキル基やニトロ基やシアノ基
やヒドロキシ基やアセチル基やハロゲンにより置換され
てもよいベンジル基、フェネチル基、フェニルプロピル
基、フェニルブチル基、ナフチルメチル基、ナフチルエ
チル基等のアラルキル基等が挙げられる。butoxy group), aryloxy group (e.g. phenoxy group, naphthoxy group), alkyl group, nitro group, cyano group, hydroxy group, acetyl group, benzyl group which may be substituted with halogen, phenethyl group, phenylpropyl group, phenyl group. Examples include aralkyl groups such as a butyl group, a naphthylmethyl group, and a naphthylethyl group.
上記した式で示される芳香族エステル化合物を構造式を
もって具体的に例示すれば以下のようなυ
Ｕυ
電荷輸送層の形成に当っては、ト記した電荷輸送物質と
芳香族エステル化合物をテトラヒドロフラン、トルエン
、メチルエチルケトン、塩化メチレンなどのような有機
溶媒に溶解若しくは分散して成る溶液を、通常の塗装法
、例えばスピニング法、浸漬法、ローラ塗布法、スプレ
ー塗布法により光電荷発生層の上に塗布したのち乾燥す
ればよい。上記した電荷輸送物質のうち低分子のものは
成膵能がないので、この場合には各種の高分子化合物を
併用して上記と同様に塗布すればよい。A concrete example of the aromatic ester compound shown by the above formula with a structural formula is the following υ
Uυ In forming the charge transport layer, a solution prepared by dissolving or dispersing the charge transport substance and aromatic ester compound mentioned above in an organic solvent such as tetrahydrofuran, toluene, methyl ethyl ketone, methylene chloride, etc. is coated with a conventional coating method. It may be applied onto the photocharge generating layer by a method such as a spinning method, a dipping method, a roller coating method, or a spray coating method, and then dried. Among the above-mentioned charge transport substances, low-molecular ones do not have the ability to grow the pancreas, so in this case, various high-molecular compounds may be used in combination and applied in the same manner as above.
このような高分子化合物としては、例えば、ポリカーボ
ネート、ポリエステルカーボネート、ポリスチレン、ポ
リ塩化ビニル、アクリル系樹脂、塩化ビニル−酢酸ビニ
ル共重合体、ポリ酢酸ビニル、ポリビニルアセタール、
フェノール樹脂、スチレン−アクリル共重合体、ボリア
リレート、およびアルキッド樹脂等の既知の電子写真感
光体用結合材料が挙げられる。ｆｔ！荷輸送層溶液は、
上記した電荷輸送材料１重量部に対し上記一般式（Ｉ）
。Examples of such polymer compounds include polycarbonate, polyester carbonate, polystyrene, polyvinyl chloride, acrylic resin, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyvinyl acetal,
Known bonding materials for electrophotographic photoreceptors include phenolic resins, styrene-acrylic copolymers, polyarylates, and alkyd resins. ft! The cargo transport layer solution is
The above general formula (I) per 1 part by weight of the above charge transport material
.
（ＩＴ）で示される芳香族エステル化合物を０．０１〜
０．５重量部、上記高分子化合物を好ましくは０．１〜
５重量部配合したものを上記有機溶媒に溶解もしくは分
散してＷ１４製すればよい。Aromatic ester compound represented by (IT) from 0.01 to
0.5 parts by weight, preferably 0.1 to 0.1 parts by weight of the above polymer compound
W14 may be prepared by dissolving or dispersing 5 parts by weight in the above organic solvent.
電荷輸送層の厚みは、通常、電荷発生層と電荷輸送層の
合計の厚みは１０〇−以下であることが好ましい。合計
の厚さが１００−を超えると、形成された被膜の可撓性
および光感度が低丁するからである。As for the thickness of the charge transport layer, it is usually preferable that the total thickness of the charge generation layer and the charge transport layer is 100 or less. This is because if the total thickness exceeds 100 mm, the flexibility and photosensitivity of the formed film will decrease.
本発明は、機能分離単層型感光体にｔ９いても上記詳説
した積層型感光体と同様に、芳香族エステル化合物を電
荷輸送物質と共に用いることにより、同様の効果を有す
るものである。According to the present invention, even if the photoreceptor is a functionally separated single layer type photoreceptor, it has the same effect as the laminated type photoreceptor detailed above by using an aromatic ester compound together with a charge transporting substance.
（実施例） 以下本発明の実施例について説明する。(Example) Examples of the present invention will be described below.
実施例１〜６
アルミニウムが蒸着されたポリエチレンテレフタレート
フィルムを導電性支持体として使用して、そのアルミニ
ウムが蒸着されている面に第１表に示すような電荷発生
物質を蒸着法または塗布法により積層させて第１表に示
すような膜厚の電荷発生層を形成した。Examples 1 to 6 A polyethylene terephthalate film on which aluminum is vapor-deposited is used as a conductive support, and a charge-generating material as shown in Table 1 is laminated on the surface on which aluminum is vapor-deposited by a vapor deposition method or a coating method. A charge generation layer having a thickness as shown in Table 1 was thus formed.
さらにこの上に、上記番号を記した芳香族エステル化合
物と、電荷輸送物質第１表に示すごとく選定して、これ
らの化合物と高分子化合物を溶解させて調整した溶液を
引上法で塗布し、９０℃で２４時間乾燥させて第１表に
示すような膜厚の電荷輸送層を形成した。Further, on top of this, a solution prepared by dissolving the aromatic ester compound with the above number and a charge transporting substance selected as shown in Table 1 and a polymer compound was applied by a pulling method. The charge transport layer was dried at 90° C. for 24 hours to form a charge transport layer having the thickness shown in Table 1.
このようにして得られた感光体の帯電能（帯電させたと
きの感光体表面電位の初期値）と光感度（表面電位初期
値が１／２に減衰するのに必要な露光Ｎ）を測定して、
その結果を第１表に示した。Measure the chargeability (initial value of photoreceptor surface potential when charged) and photosensitivity (exposure N required for the initial value of surface potential to attenuate to 1/2) of the photoreceptor thus obtained. do,
The results are shown in Table 1.
また、感光体の暗減衰率（暗中における感光体表面電位
の減衰率）および残留電位（露光により表面電位減衰が
急激に遅くなるところ）は第１表に示す通りであった。Further, the dark decay rate (decay rate of photoconductor surface potential in the dark) and residual potential (where the surface potential decay rapidly slows down due to exposure) of the photoconductor were as shown in Table 1.
この感光体を熱、オゾン等の発生環境下で帯電、露光を
１０，０００回反復したところ、はとんど異常が認めら
れず帯電能、光感度、残留電位等の変動が小さく耐疲労
特性に優れていることが判明した。When this photoreceptor was repeatedly charged and exposed 10,000 times in an environment where heat, ozone, etc. were generated, almost no abnormality was observed, and fluctuations in charging ability, photosensitivity, residual potential, etc. were small, and fatigue resistance was achieved. It turned out to be excellent.
（以下余白）
比較例１〜２
電荷輸送物として芳香族エステル化合物を用いない他は
、実施例と同様にして電子写真感光体を作成した。(The following is a blank space) Comparative Examples 1 and 2 Electrophotographic photoreceptors were produced in the same manner as in the examples except that an aromatic ester compound was not used as a charge transport material.
この感光体の帯電能、光感度、暗減衰率、残留電位を測
定して第１表に示した。The charging ability, photosensitivity, dark decay rate, and residual potential of this photoreceptor were measured and shown in Table 1.
この感光体を熱、オゾン等の発生環境下で、帯電、露光
を１０，０００回反復したところ帯電能、光感度、残留
電位等の変動が認められ、耐疲労特性が実施例と比較し
て劣っていた。When this photoreceptor was repeatedly charged and exposed 10,000 times in an environment where heat, ozone, etc. were generated, changes in charging ability, photosensitivity, residual potential, etc. were observed, and the fatigue resistance was compared with the example. It was inferior.
以上、実施例の結果から明らかなように、本発明の電子
写真感光体は、暗減衰率が少なく、帯電能が大きく優れ
た帯電特性を有すると共に、半減露光祉が少なく優れた
光感度特性を有するものである。また、本発明の電子写
真感光体は、光、熱、オゾンに対して安定性を有し、長
時間の使用に際しても安定した帯電特性、光感度特性お
よび残留電位特性を保持するものであり、優れた耐久性
を有するものである。As is clear from the results of the examples above, the electrophotographic photoreceptor of the present invention has excellent charging characteristics with a small dark decay rate and large charging ability, as well as excellent photosensitivity characteristics with low half-decrease exposure stability. It is something that you have. Furthermore, the electrophotographic photoreceptor of the present invention has stability against light, heat, and ozone, and maintains stable charging characteristics, photosensitivity characteristics, and residual potential characteristics even when used for a long time. It has excellent durability.
Claims (1)
含有する感光層を設けて成る電子写真感光体において該
感光層が下記一般式（ I ）及び／又は（II）で示され
る芳香族エステル化合物を少なくとも一種含有すること
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▼（ I ） ▲数式、化学式、表等があります▼（II） 式中Ｒ＿１〜Ｒ＿４は置換されてもよいフェニル基を示
し同じであっても異なっていてもよい Ｒ＿５は置換されてもよいフェニル基又は−Ａ−Ｘ−Ｂ
−で示され Ａ、Ｂは置換されてもよいフェニル基、 Ｘは２価のアルキル基又はシクロアルキル基、アラルキ
ル基、アリール基である(1) In an electrophotographic photoreceptor comprising a photosensitive layer containing a charge generating substance and a charge transporting substance provided on a conductive support, the photosensitive layer has an aroma represented by the following general formula (I) and/or (II). An electrophotographic photoreceptor comprising at least one group ester compound. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) In the formula, R_1 to R_4 represent phenyl groups that may be substituted and may be the same or different. Good R_5 is an optionally substituted phenyl group or -A-X-B
-, A and B are optionally substituted phenyl groups, and X is a divalent alkyl group, cycloalkyl group, aralkyl group, or aryl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29877686A JPS63151952A (en) | 1986-12-17 | 1986-12-17 | Electrophotographic sensitive body |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29877686A JPS63151952A (en) | 1986-12-17 | 1986-12-17 | Electrophotographic sensitive body |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63151952A true JPS63151952A (en) | 1988-06-24 |
Family
ID=17864066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29877686A Pending JPS63151952A (en) | 1986-12-17 | 1986-12-17 | Electrophotographic sensitive body |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63151952A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016216458A (en) * | 2015-05-22 | 2016-12-22 | 本州化学工業株式会社 | Novel 1,1-bis(4-acyloxyphenyl)-3,3,5-trimethylcyclohexanes |
-
1986
- 1986-12-17 JP JP29877686A patent/JPS63151952A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016216458A (en) * | 2015-05-22 | 2016-12-22 | 本州化学工業株式会社 | Novel 1,1-bis(4-acyloxyphenyl)-3,3,5-trimethylcyclohexanes |
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