JPH04281461A - Electrophotographic sensitive material - Google Patents
Electrophotographic sensitive materialInfo
- Publication number
- JPH04281461A JPH04281461A JP6906691A JP6906691A JPH04281461A JP H04281461 A JPH04281461 A JP H04281461A JP 6906691 A JP6906691 A JP 6906691A JP 6906691 A JP6906691 A JP 6906691A JP H04281461 A JPH04281461 A JP H04281461A
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- formula
- electrophotographic photoreceptor
- alkyl group
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 title abstract description 6
- 239000011241 protective layer Substances 0.000 claims abstract description 26
- 239000010410 layer Substances 0.000 claims abstract description 25
- 239000011230 binding agent Substances 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 11
- 239000011347 resin Substances 0.000 claims abstract description 11
- 229910052751 metal Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 9
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 9
- 239000000843 powder Substances 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims description 96
- 108091008695 photoreceptors Proteins 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 230000005525 hole transport Effects 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
- -1 methylenedioxy groups Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000005577 anthracene group Chemical group 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 abstract description 8
- QGJXVBICNCIWEL-UHFFFAOYSA-N 9-ethylcarbazole-3-carbaldehyde Chemical compound O=CC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 QGJXVBICNCIWEL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000006185 dispersion Substances 0.000 abstract description 2
- 239000012876 carrier material Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 description 14
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 5
- DXYYLUGHPCHMRQ-UHFFFAOYSA-N n,n-diphenyl-4-(2-phenylethenyl)aniline Chemical compound C=1C=CC=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 DXYYLUGHPCHMRQ-UHFFFAOYSA-N 0.000 description 5
- CLQYLLIGYDFCGY-UHFFFAOYSA-N 4-(2-anthracen-9-ylethenyl)-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=C(C=CC=C2)C2=CC2=CC=CC=C12 CLQYLLIGYDFCGY-UHFFFAOYSA-N 0.000 description 4
- GAYAMEKFIBYRJW-UHFFFAOYSA-N 4-(fluoren-9-ylidenemethyl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=C1C2=CC=CC=C2C2=CC=CC=C21 GAYAMEKFIBYRJW-UHFFFAOYSA-N 0.000 description 4
- BZKRKPGZABEOSM-XMHGGMMESA-N 4-[(e)-2-[3-[4-(diethylamino)phenyl]-2-phenyl-3,4-dihydropyrazol-5-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1\C=C\C1=NN(C=2C=CC=CC=2)C(C=2C=CC(=CC=2)N(CC)CC)C1 BZKRKPGZABEOSM-XMHGGMMESA-N 0.000 description 4
- ZTYUDPDLRTYFCU-UHFFFAOYSA-N 4-[2-[2-[2-[4-(diethylamino)phenyl]ethenyl]phenyl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC=CC=C1C=CC1=CC=C(N(CC)CC)C=C1 ZTYUDPDLRTYFCU-UHFFFAOYSA-N 0.000 description 4
- 229910021417 amorphous silicon Inorganic materials 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- OJBSYCMUWONLAE-UHFFFAOYSA-N n,n,4-triphenylaniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OJBSYCMUWONLAE-UHFFFAOYSA-N 0.000 description 4
- GACNTLAEHODJKY-UHFFFAOYSA-N n,n-dibenzyl-4-[1-[4-(dibenzylamino)phenyl]propyl]aniline Chemical compound C=1C=C(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(CC)C(C=C1)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 GACNTLAEHODJKY-UHFFFAOYSA-N 0.000 description 4
- QYXUHIZLHNDFJT-UHFFFAOYSA-N n-[(9-ethylcarbazol-3-yl)methylideneamino]-n-methylaniline Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=NN(C)C1=CC=CC=C1 QYXUHIZLHNDFJT-UHFFFAOYSA-N 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- NIZIGUQDQIALBQ-UHFFFAOYSA-N 4-(2,2-diphenylethenyl)-n,n-diphenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 NIZIGUQDQIALBQ-UHFFFAOYSA-N 0.000 description 3
- WWJNSMFFLNLWLI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-(4-phenylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(C)C=C1 WWJNSMFFLNLWLI-UHFFFAOYSA-N 0.000 description 3
- FVGPNZKTTWPLOC-UHFFFAOYSA-N 9-ethyl-3-(2-phenylethenyl)carbazole Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=CC1=CC=CC=C1 FVGPNZKTTWPLOC-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910003437 indium oxide Inorganic materials 0.000 description 3
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- AOLUMCPVEUKWBX-UHFFFAOYSA-N 1-[2-[2-[2-(2,4-dimethoxyphenyl)ethenyl]phenyl]ethenyl]-2,4-dimethoxybenzene Chemical compound COC1=CC(OC)=CC=C1C=CC1=CC=CC=C1C=CC1=CC=C(OC)C=C1OC AOLUMCPVEUKWBX-UHFFFAOYSA-N 0.000 description 2
- VWEQSBRKYZRWPQ-UHFFFAOYSA-N 4-[2-(10-bromoanthracen-9-yl)ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=C(C=CC=C2)C2=C(Br)C2=CC=CC=C12 VWEQSBRKYZRWPQ-UHFFFAOYSA-N 0.000 description 2
- NEZCBMZHMQVZOD-UHFFFAOYSA-N 4-[2-[3-[4-(dimethylamino)phenyl]-2-phenyl-1,3-dihydropyrazol-5-yl]ethenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)N(C)C)N(C=2C=CC=CC=2)N1 NEZCBMZHMQVZOD-UHFFFAOYSA-N 0.000 description 2
- SBMCZDLOXDWNIN-UHFFFAOYSA-N 4-[bis[4-(diethylamino)phenyl]methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)C1=CC=C(N(CC)CC)C=C1 SBMCZDLOXDWNIN-UHFFFAOYSA-N 0.000 description 2
- 229910017000 As2Se3 Inorganic materials 0.000 description 2
- OBAPJZDFDIJDKV-UHFFFAOYSA-N C1=CC(N(CC)CC)=CC=C1C=C=NN(C)C1=CC=CC=C1 Chemical compound C1=CC(N(CC)CC)=CC=C1C=C=NN(C)C1=CC=CC=C1 OBAPJZDFDIJDKV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910001370 Se alloy Inorganic materials 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UAVOVDWXWRXKPS-UHFFFAOYSA-N n-[(4-methoxyphenyl)methylideneamino]-n-methylaniline Chemical compound C1=CC(OC)=CC=C1C=NN(C)C1=CC=CC=C1 UAVOVDWXWRXKPS-UHFFFAOYSA-N 0.000 description 2
- HIWDRSNALOGCSA-UHFFFAOYSA-N n-benzyl-n-[(4-methoxynaphthalen-1-yl)methylideneamino]aniline Chemical compound C12=CC=CC=C2C(OC)=CC=C1C=NN(C=1C=CC=CC=1)CC1=CC=CC=C1 HIWDRSNALOGCSA-UHFFFAOYSA-N 0.000 description 2
- RPHJRJPXKZMFFQ-UHFFFAOYSA-N n-benzyl-n-[(9-ethylcarbazol-3-yl)methylideneamino]aniline Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=NN(C=1C=CC=CC=1)CC1=CC=CC=C1 RPHJRJPXKZMFFQ-UHFFFAOYSA-N 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- CBJPRTGKMYOVJO-UHFFFAOYSA-N 1-phenyl-2-(2-phenylethenyl)benzene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1C1=CC=CC=C1 CBJPRTGKMYOVJO-UHFFFAOYSA-N 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
- ZRAAQCHSVXWRJN-UHFFFAOYSA-N 2-(1,2-diphenylethenyl)-n,n-diphenylaniline Chemical compound C=1C=CC=CC=1C=C(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 ZRAAQCHSVXWRJN-UHFFFAOYSA-N 0.000 description 1
- WDFBSMBVBUXHRP-UHFFFAOYSA-N 2-[2-(4-methylphenyl)-1-phenylethenyl]-n-phenylaniline Chemical compound C1=CC(C)=CC=C1C=C(C=1C(=CC=CC=1)NC=1C=CC=CC=1)C1=CC=CC=C1 WDFBSMBVBUXHRP-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- CUDANNOCLGTWLM-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)-n-[4-(2-phenylethenyl)phenyl]aniline Chemical compound CC1=CC=CC=C1N(C=1C(=CC=CC=1)C)C(C=C1)=CC=C1C=CC1=CC=CC=C1 CUDANNOCLGTWLM-UHFFFAOYSA-N 0.000 description 1
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 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
- AEEHOVNCLFTKTO-UHFFFAOYSA-N 4-[[benzyl(phenyl)hydrazinylidene]methyl]-n,n-diphenylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)N=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 AEEHOVNCLFTKTO-UHFFFAOYSA-N 0.000 description 1
- MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-UHFFFAOYSA-N 0.000 description 1
- FCVBQVZQLJLPBU-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-[4-(2,4,6-trimethylphenyl)phenyl]aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C(=CC(C)=CC=1C)C)C1=CC=C(C)C=C1 FCVBQVZQLJLPBU-UHFFFAOYSA-N 0.000 description 1
- PILONTKKEDAWGG-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-[4-(4-methylphenyl)phenyl]aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 PILONTKKEDAWGG-UHFFFAOYSA-N 0.000 description 1
- BODPVHGDJHVWAW-UHFFFAOYSA-N 9-ethyl-3-[2-(4-methoxyphenyl)ethenyl]carbazole Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=CC1=CC=C(OC)C=C1 BODPVHGDJHVWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229910018110 Se—Te Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229910000416 bismuth oxide Inorganic materials 0.000 description 1
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 description 1
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 description 1
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- OJVNNLDLHOFPFQ-UHFFFAOYSA-N n,n-dibenzyl-4-(2-phenylethenyl)aniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC(C=CC=2C=CC=CC=2)=CC=1)CC1=CC=CC=C1 OJVNNLDLHOFPFQ-UHFFFAOYSA-N 0.000 description 1
- BVTXDOPTUCCGGU-UHFFFAOYSA-N n,n-diethyl-4-(2-naphthalen-1-ylethenyl)aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC=CC2=CC=CC=C12 BVTXDOPTUCCGGU-UHFFFAOYSA-N 0.000 description 1
- PGNGDPCGHVDYBE-UHFFFAOYSA-N n-(9h-carbazol-3-ylmethylideneamino)-n-phenylaniline Chemical compound C=1C=C2NC3=CC=CC=C3C2=CC=1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 PGNGDPCGHVDYBE-UHFFFAOYSA-N 0.000 description 1
- MKIVRGOMSLSEOM-UHFFFAOYSA-N n-[4-(4-ethylphenyl)phenyl]-4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(CC)=CC=C1C1=CC=C(N(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)C=C1 MKIVRGOMSLSEOM-UHFFFAOYSA-N 0.000 description 1
- ZQKFNYHHBMBPHU-UHFFFAOYSA-N n-benzyl-n-[(2,4-dimethoxyphenyl)methylideneamino]aniline Chemical compound COC1=CC(OC)=CC=C1C=NN(C=1C=CC=CC=1)CC1=CC=CC=C1 ZQKFNYHHBMBPHU-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) 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
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は表面保護層を有する電子
写真用感光体に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photoreceptor having a surface protective layer.
【０００２】0002
【従来の技術】従来、電子写真感光体としては、導電性
支持体上にセレンないしセレン合金を主体とする光導電
層を設けたもの、酸化亜鉛、酸化カドミウムなどの無機
光導電材料をバインダー中に分散させたもの、ポリ−Ｎ
−ビニルカルバゾールとトリニトロフルオレノンあるい
はアゾ顔料などの有機光導電材料を用いたもの及び非晶
質シリコンを用いたもの等が一般に知られている。これ
らの感光体に対して、長時間高画質を保つ信頼性の要求
が年々高まっている。しかし光導電層が露出している場
合、帯電過程のコロナ放電による損傷と複写プロセスで
受ける他部材との接触による物理的あるいは化学的な損
傷が感光体の寿命を損なうものであった。[Prior Art] Conventionally, electrophotographic photoreceptors have been prepared by providing a photoconductive layer mainly made of selenium or a selenium alloy on a conductive support, or by using an inorganic photoconductive material such as zinc oxide or cadmium oxide as a binder. Poly-N
- Those using organic photoconductive materials such as vinyl carbazole and trinitrofluorenone or azo pigments, and those using amorphous silicon are generally known. For these photoreceptors, the demand for reliability that maintains high image quality for a long period of time is increasing year by year. However, when the photoconductive layer is exposed, damage caused by corona discharge during the charging process and physical or chemical damage caused by contact with other members during the copying process impair the life of the photoreceptor.
【０００３】このような欠点を解消する方法として感光
体表面に保護層を設ける技術が知られている。具体的に
は感光層の表面に有機フィルムを設ける方法（特公昭３
８−１５４４６）、無機酸化物を設ける方法（特公昭４
３−１４５１７）、接着層を設けた後、絶縁層を積層す
る方法（特公昭４３−２７５９１）、あるいはプラズマ
ＣＶＤ法・光ＣＶＤ法等によってａ−Ｓｉ層、ａ−Ｓｉ
：Ｎ：Ｈ層、ａ−Ｓｉ：Ｏ：Ｈ層等を積層する方法（特
開昭５７−１７９８５９、特開昭５９−５８４３７）が
開示されている。しかしながら、保護層が電子写真的に
高抵抗（１０１４Ω・ｃｍ以上）になると、残留電位の
増大、繰返時の蓄積などが問題となり、実用上好ましく
ない。[0003] As a method for eliminating such drawbacks, a technique is known in which a protective layer is provided on the surface of the photoreceptor. Specifically, a method of providing an organic film on the surface of the photosensitive layer (Japanese Patent Publication No. 3)
8-15446), method of providing inorganic oxide (Special Publication No. 4
A-Si layer, a-Si
:N:H layer, a-Si:O:H layer, etc. have been disclosed (Japanese Patent Laid-Open Nos. 57-179859 and 59-58437). However, if the protective layer becomes electrophotographically high in resistance (10<14 >Ω·cm or more), problems such as an increase in residual potential and accumulation during repetition will arise, which is not preferred in practice.
【０００４】上記欠点を補う技術として保護層を光導電
層とする方法（特公昭４８−３８４２７、特公昭４３−
１６１９８、特公昭４９−１０２５８、ＵＳＰ−２９０
１３４８）、保護層中に色素やルイス酸に代表される移
動剤を添加する方法（特公昭４４−８３４、特開昭５３
−１３３４４４）、或いは金属や金属酸化物微粒子の添
加により保護層の抵抗を制御する方法（特開昭５３−３
３３８）等が提案されている。しかし、このような場合
には保護層による光の吸収が生じ光導電層へ到達する光
量が減少するため、結果として電子写真用感光体の感度
が低下するという問題が生じる。[0004] As a technique to compensate for the above-mentioned drawbacks, a method of using a photoconductive layer as a protective layer (Japanese Patent Publication No. 48-38427, Japanese Patent Publication No. 43-1982)
16198, Special Publication Showa 49-10258, USP-290
1348), a method of adding a transfer agent such as a dye or a Lewis acid to the protective layer (Japanese Patent Publication No. 44-834, Japanese Patent Application Laid-Open No. 1987-53
-133444), or a method of controlling the resistance of the protective layer by adding metal or metal oxide fine particles (JP-A-53-3)
338) etc. have been proposed. However, in such a case, the protective layer absorbs light and the amount of light reaching the photoconductive layer decreases, resulting in a problem that the sensitivity of the electrophotographic photoreceptor decreases.
【０００５】この様な観点から特開昭５７−３０８４６
に開示されているように平均粒径０．３μｍ以下の金属
酸化物微粒子を抵抗制御剤として表面保護層中に分散さ
せることにより、可視光に対して実質的に透明にする方
法がある。この表面保護層をもった電子写真用感光体は
感度低下も少なく、表面保護層の機械的強度も増し、耐
久性が向上する。しかしながら、この感光体を実際の複
写機に組み込んだ場合、残留電位が生じ画像上に地肌汚
れを発生させるという欠点がある。この残留電位は表面
保護層上に蓄積した残留電荷により発生し、特に低温低
湿時に著しく増大する。From this point of view, Japanese Patent Application Laid-Open No. 57-30846
There is a method of making the surface substantially transparent to visible light by dispersing metal oxide fine particles having an average particle size of 0.3 μm or less as a resistance control agent in the surface protective layer, as disclosed in . An electrophotographic photoreceptor having this surface protective layer exhibits little decrease in sensitivity, increases the mechanical strength of the surface protective layer, and improves durability. However, when this photoreceptor is incorporated into an actual copying machine, there is a drawback that a residual potential is generated, causing background stains on the image. This residual potential is generated by residual charges accumulated on the surface protective layer, and increases significantly especially at low temperature and low humidity.
【０００６】[0006]
【発明が解決しようとする課題】本発明はこうした実情
に鑑み、高い機械的強度を備えかつ低湿時に残留電位の
増加を生じない安定な電気特性を示す保護層を有し、長
期に渡って品質の高い画像を安定して形成しうる電子写
真用感光体を提供することを目的とする。[Problems to be Solved by the Invention] In view of these circumstances, the present invention has a protective layer that has high mechanical strength and exhibits stable electrical properties that do not cause an increase in residual potential at low humidity. An object of the present invention is to provide an electrophotographic photoreceptor that can stably form images with high image quality.
【０００７】[0007]
【課題を解決するための手段】本発明は、導電性支持体
上に光導電層及び表面保護層を順次積層した電子写真用
感光体において、表面保護層が金属あるいは金属酸化物
微粉末を結着樹脂中に分散させた層からなり、かつ正孔
搬送物質を含有させたことを特徴とするものであり、該
正孔搬送物質として、例えば次に示す化１〜化１３で表
わされる化合物を用いることを特徴とするものであり、
また、該正孔搬送物質と該結着樹脂との重量比が１：９
９〜５０：５０であることを特徴とするものである。[Means for Solving the Problems] The present invention provides an electrophotographic photoreceptor in which a photoconductive layer and a surface protective layer are sequentially laminated on a conductive support, in which the surface protective layer binds metal or metal oxide fine powder. It is characterized by comprising a layer dispersed in a binder resin and containing a hole transporting substance, and as the hole transporting substance, for example, compounds represented by the following chemical formulas 1 to 13 are used. It is characterized by the use of
Further, the weight ratio of the hole transport substance and the binder resin is 1:9.
The ratio is 9 to 50:50.
【０００８】[0008]
【化１】
〔式中、Ｒ１はアルキル基、ベンジル基、フェニル基を
表わし、Ｒ１は水素、炭素数１〜３のアルキル基、炭素
数１〜３のアルコキシ基、ジアルキルアミノ基、ジアラ
ルキルアミノ基またはジアリールアミノ基を表わし、ｎ
は１〜４の整数を表わし、ｎが２以上のときＲ２は同じ
でも異なっていてもよい。Ｒ３は水素またはメトキシ基
を表わす。〕[Formula 1] [In the formula, R1 represents an alkyl group, a benzyl group, or a phenyl group, and R1 is hydrogen, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a dialkylamino group, or a dialkylamino group. group or diarylamino group, n
represents an integer of 1 to 4, and when n is 2 or more, R2 may be the same or different. R3 represents hydrogen or a methoxy group. ]
【０００９】[0009]
【化２】
〔式中、Ｒ１はメチル基、エチル基、２−ヒドロキシエ
チル基又は２−クロルエチル基を表わし、Ｒ２はメチル
基、エチル基、ベンジル基又はフェニル基を表わし、Ｒ
３は水素、塩素、臭素、炭素数１〜４のアルキル基、炭
素数１〜４のアルコキシ基、ジアルキルアミノ基又はニ
トロ基を表わす。〕[Formula, R1 represents a methyl group, ethyl group, 2-hydroxyethyl group or 2-chloroethyl group, R2 represents a methyl group, ethyl group, benzyl group or phenyl group, R
3 represents hydrogen, chlorine, bromine, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a dialkylamino group, or a nitro group. ]
【００１０】0010
【化３】
〔式中、Ａｒはナフタリン環、アントラセン環、スチリ
ル基及びそれらの置換体あるいはピリジン環、フラン環
、チオフェン環を表わし、Ｒはアルキル基又はベンジル
基を表わす。〕embedded image [In the formula, Ar represents a naphthalene ring, an anthracene ring, a styryl group, or a substituted product thereof, or a pyridine ring, a furan ring, or a thiophene ring, and R represents an alkyl group or a benzyl group. ]
【００１１】[0011]
【化４】
〔式中、Ａ１，Ａ２は置換もしくは無置換のアルキル基
又は置換もしくは無置換のアリール基を表わし、それぞ
れ同一でも異なっていてもよい。Ａｒは置換または無置
換の縮合多環式炭化水素基を表わす。〕embedded image [In the formula, A1 and A2 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and may be the same or different. Ar represents a substituted or unsubstituted condensed polycyclic hydrocarbon group. ]
【００１２】0012
【化５】
〔式中、Ｒ１，Ｒ３及びＲ４は水素原子、アミノ基、ア
ルコキシ基、チオアルコキシ基、アリールオキシ基、メ
チレンジオキシ基、置換もしくは無置換のアルキル基、
ハロゲン原子又は置換もしくは無置換のアリール基を、
Ｒ２は水素原子、アルコキシ基、置換もしくは無置換の
アルキル基又はハロゲンを表わす。ｋは１〜５の整数、
ｌは１〜４の整数、ｍは１〜５の整数、ｎは１〜５の整
数である。〕[Formula 5, R1, R3 and R4 are hydrogen atoms, amino groups, alkoxy groups, thioalkoxy groups, aryloxy groups, methylenedioxy groups, substituted or unsubstituted alkyl groups,
A halogen atom or a substituted or unsubstituted aryl group,
R2 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group, or a halogen. k is an integer from 1 to 5,
l is an integer of 1 to 4, m is an integer of 1 to 5, and n is an integer of 1 to 5. ]
【００１３】[0013]
【化６】
〔式中Ｒ１は水素、ハロゲン、シアノ基、炭素数１〜４
のアルコキシ基または炭素数１〜４のアルキル基を表わ
し、Ａｒは
Ｒ２は炭素数１〜４のアルキル基を表わし、Ｒ３は水素
、ハロゲン、炭素数１〜４のアルキル基、炭素数１〜４
のアルコキシ基またはジアルキルアミノ基を表わし、ｎ
は１または２であって、ｎが２のときはＲ３は同一でも
異なってもよく、Ｒ４およびＲ５は水素、炭素数１〜４
の置換または無置換のアルキル基あるいは置換または無
置換のベンジル基を表わす。〕[Formula R1 is hydrogen, halogen, cyano group, carbon number 1-4
represents an alkoxy group or an alkyl group having 1 to 4 carbon atoms, Ar is R2 represents an alkyl group having 1 to 4 carbon atoms, and R3 is hydrogen, halogen, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms.
represents an alkoxy group or dialkylamino group, n
is 1 or 2, and when n is 2, R3 may be the same or different, R4 and R5 are hydrogen, and have 1 to 4 carbon atoms.
represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted benzyl group. ]
【００１４】[0014]
【化７】
〔式中、Ｒ１は炭素数１〜１１のアルキル基、置換もし
くは無置換のフェニル基又は複素環基を表わし、Ｒ２，
Ｒ３はそれぞれ同一でも異なっていてもよく水素、炭素
数１〜４のアルキル基、ヒドロキシアルキル基、クロル
アルキル基、置換または無置換のアラルキル基を表わし
、また、Ｒ２とＲ３は互いに結合し窒素を含む複素環を
形成していてもよい。Ｒ４は同一でも異なっていてもよ
く水素、炭素数１〜４のアルキル基、アルコキシ基又は
ハロゲンを表わす。〕[In the formula, R1 represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group, or a heterocyclic group, R2,
R3 may be the same or different and each represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group, a chloroalkyl group, a substituted or unsubstituted aralkyl group, and R2 and R3 are bonded to each other and represent nitrogen. may form a heterocycle containing. R4 may be the same or different and represents hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group, or a halogen. ]
【００１５】[0015]
【化８】
〔式中、Ｒはカルバゾリル基、ピリジル基、チエニル基
、インドリル基、フリル基或いはそれぞれ置換もしくは
無置換のフェニル基、スチリル基、ナフチル基またはア
ントリル基であって、これらの置換基がジアルキルアミ
ノ基、アルキル基、アルコキシ基、カルボキシ基または
そのエステル、ハロゲン原子、シアノ基、アラルキルア
ミノ基、Ｎ−アルキル−Ｎ−アラルキルアミノ基、アミ
ノ基、ニトロ基およびアセチルアミノ基からなる群から
選ばれた基を表わす。〕[Formula 8] [In the formula, R is a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group, or an anthryl group, and these substituents is from the group consisting of a dialkylamino group, an alkyl group, an alkoxy group, a carboxy group or an ester thereof, a halogen atom, a cyano group, an aralkylamino group, an N-alkyl-N-aralkyl amino group, an amino group, a nitro group, and an acetylamino group Represents the selected group. ]
【００１６】[0016]
【化９】
〔式中、ｎは０または１の整数、Ｒ１は水素原子、アル
キル基または置換もしくは無置換のフェニル基を示し、
Ａは
９−アントリル基または置換もしくは無置換のＮ−アル
キルカルバゾリル基を表わし、ここでＲ２は水素原子、
アルキル基、アルコキシ基、ハロゲン原子または（但し
、Ｒ３およびＲ４はアルキル基、置換または無置換のア
ラルキル基、置換または無置換のアリール基を示し、Ｒ
３およびＲ４は環を形成してもよい）を表わし、ｍは０
，１，２または３の整数であって、ｍが２以上まときは
Ｒ２は同一でも異なってもよい。〕[In the formula, n is an integer of 0 or 1, R1 represents a hydrogen atom, an alkyl group, or a substituted or unsubstituted phenyl group,
A represents a 9-anthryl group or a substituted or unsubstituted N-alkylcarbazolyl group, where R2 is a hydrogen atom,
an alkyl group, an alkoxy group, a halogen atom or (where R3 and R4 represent an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group,
3 and R4 may form a ring), m is 0
, 1, 2 or 3, and when m is 2 or more, R2 may be the same or different. ]
【００１７】[0017]
【化１０】
〔式中、Ｒ１は低級アルキル基またはベンジル基を表わ
し、Ｒ２は水素原子、低級アルキル基、低級アルコキシ
基、ハロゲン原子、ニトロ基、アミノ基あるいは低級ア
ルキル基またはベンジル基で置換されたアミノ基を表わ
し、ｎは１または２の整数を表わす。〕[In the formula, R1 represents a lower alkyl group or a benzyl group, and R2 is substituted with a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group, a lower alkyl group, or a benzyl group] represents an amino group, and n represents an integer of 1 or 2. ]
【００１８】[0018]
【化１１】
〔式中、Ｒ１は水素原子、アルキル基、アルコキシ基ま
たはハロゲン原子を表わし、Ｒ２およびＲ３はアルキル
基、置換または無置換のアラルキル基あるいは置換また
は無置換のアリール基を表わし、Ｒ４は水素原子または
置換もしくは無置換のフェニル基を表わし、また、Ａｒ
はフェニル基またはナフチル基を表わす。〕[In the formula, R1 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, R2 and R3 represent an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, and R4 represents a hydrogen atom or a substituted or unsubstituted phenyl group, and Ar
represents a phenyl group or a naphthyl group. ]
【００１９
】0019
]
【化１２】
〔式中、Ｒは水素またはハロゲン原子を表わし、Ａｒは
置換または無置換のフェニル基、ナフチル基、アントリ
ル基あるいはカルバゾリル基を表わす。〕embedded image [In the formula, R represents hydrogen or a halogen atom, and Ar represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group, or carbazolyl group. ]
【００２０】[0020]
【化１３】
〔式中、Ｒ１，Ｒ２およびＲ３は水素、低級アルキル基
、低級アルコキシ基、ジアルキルアミノ基またはハロゲ
ン原子を表わし、ｎは０または１を表わす。〕embedded image [In the formula, R1, R2 and R3 represent hydrogen, a lower alkyl group, a lower alkoxy group, a dialkylamino group or a halogen atom, and n represents 0 or 1. ]
【００２
１】以下、本発明をさらに詳しく説明する。本発明に用
いられる正孔搬送物質としては次のようなものが挙げら
れる。化１で示される具体例としては、４−メトキシベ
ンズアルデヒド１−メチル−１−フェニルヒドラゾン、
２，４−ジメトキシベンズアルデヒド１−ベンジル−１
−フェニルヒドラゾン、４−ジエチルアミノベンズアル
デヒド１，１−ジフェニルヒドラゾン、４−メトキシベ
ンズアルデヒド１−ベンジル−１−（４−メトキシ）フ
ェニルヒドラゾン、４−ジフェニルアミノベンズアルデ
ヒド１−ベンジル−１−フェニルヒドラゾン、４−ジベ
ンジルアミノベンズアルデヒド１，１−ジフェニルヒド
ラゾンなどがある。002
1] The present invention will be explained in more detail below. Examples of the hole transport substance used in the present invention include the following. Specific examples of formula 1 include 4-methoxybenzaldehyde 1-methyl-1-phenylhydrazone,
2,4-dimethoxybenzaldehyde 1-benzyl-1
-Phenylhydrazone, 4-diethylaminobenzaldehyde 1,1-diphenylhydrazone, 4-methoxybenzaldehyde 1-benzyl-1-(4-methoxy)phenylhydrazone, 4-diphenylaminobenzaldehyde 1-benzyl-1-phenylhydrazone, 4-diphenylaminobenzaldehyde Examples include benzylaminobenzaldehyde 1,1-diphenylhydrazone.
【００２２】化２で表わされる具体例としては、９−エ
チルカルバゾール−３−アルデヒド１−メチル−１−フ
ェニルヒドラゾン、９−エチルカルバゾール−３−アル
デヒド１−ベンジル−１−フェニルヒドラゾン、９−エ
チルカルバゾール−３−アルデヒド１，１−ジフェニル
ヒドラゾンなどがある。Specific examples of formula 2 include 9-ethylcarbazole-3-aldehyde 1-methyl-1-phenylhydrazone, 9-ethylcarbazole-3-aldehyde 1-benzyl-1-phenylhydrazone, and 9-ethylcarbazole-3-aldehyde 1-benzyl-1-phenylhydrazone. Examples include carbazole-3-aldehyde 1,1-diphenylhydrazone.
【００２３】化３で表わされる具体例としては、４−ジ
エチルアミノスチレン−β−アルデヒド１−メチル−１
−フェニルヒドラゾン、４−メトキシナフタレン−１−
アルデヒド１−ベンジル−１−フェニルヒドラゾンなど
がある。Specific examples of formula 3 include 4-diethylaminostyrene-β-aldehyde 1-methyl-1
-Phenylhydrazone, 4-methoxynaphthalene-1-
Examples include aldehyde 1-benzyl-1-phenylhydrazone.
【００２４】化４で表わされる具体例としては、１−Ｎ
，Ｎ−ビス（４−メチルフェニル）アミノピレン、１−
Ｎ，Ｎ−ビス（３−メチルフェニル）アミノピレン。As a specific example represented by chemical formula 4, 1-N
, N-bis(4-methylphenyl)aminopyrene, 1-
N,N-bis(3-methylphenyl)aminopyrene.
【００２５】化５で表わされる具体例としては、Ｎ，Ｎ
−ジフェニル−〔１，１’−ビフェニル〕−４−アミン
、Ｎ，Ｎ−ビス（４−メチルフェニル）−〔１，１’−
ビフェニル〕−４−アミン、Ｎ，Ｎ−ビス（４−メチル
フェニル）−〔１，１’−ビフェニル〕−４−アミン、
４’−メチル−Ｎ，Ｎ−ビス（４−メチルフェニル）−
〔１，１’−ビフェニル〕−４−アミン、４’−エチル
−Ｎ，Ｎ−ビス（４−メチルフェニル）−〔１，１’−
ビフェニル〕−４−アミン、４’−ｔ−ブチル−Ｎ，Ｎ
−ビス（３−メチルフェニル）−〔１，１’−ビフェニ
ル〕−４−アミン、２’，４’，６’−トリメチル−Ｎ
，Ｎ−ビス（４−メチルフェニル）−〔１，１’−ビフ
ェニル〕−４−アミン、３−メチル−３’−メチル−Ｎ
−４−メトキシフェニル−Ｎ−４−メチルフェニル）−
〔１，１’−ビフェニル〕−４−アミン、４’−フェノ
キシ−Ｎ，Ｎ−ビス（４−クロルフェニル）−〔１，１
’−ビフェニル〕−４−アミン、４’−ベンジル−Ｎ，
Ｎ−ビス（２−エチルフェニル）−〔１，１’−ビフェ
ニル〕−４−アミン。As a specific example represented by chemical formula 5, N, N
-diphenyl-[1,1'-biphenyl]-4-amine, N,N-bis(4-methylphenyl)-[1,1'-
biphenyl]-4-amine, N,N-bis(4-methylphenyl)-[1,1'-biphenyl]-4-amine,
4'-Methyl-N,N-bis(4-methylphenyl)-
[1,1'-biphenyl]-4-amine, 4'-ethyl-N,N-bis(4-methylphenyl)-[1,1'-
biphenyl]-4-amine, 4'-t-butyl-N,N
-bis(3-methylphenyl)-[1,1'-biphenyl]-4-amine, 2',4',6'-trimethyl-N
, N-bis(4-methylphenyl)-[1,1'-biphenyl]-4-amine, 3-methyl-3'-methyl-N
-4-methoxyphenyl-N-4-methylphenyl)-
[1,1'-biphenyl]-4-amine, 4'-phenoxy-N,N-bis(4-chlorophenyl)-[1,1
'-Biphenyl]-4-amine, 4'-benzyl-N,
N-bis(2-ethylphenyl)-[1,1'-biphenyl]-4-amine.
【００２６】化６で表わされる具体例としては、９−（
４−ジメチルアミノベンジリデン）フルオレン、３−（
９−フルオレニリデン）−９−エチルカルバゾールなど
がある。As a specific example represented by chemical formula 6, 9-(
4-dimethylaminobenzylidene) fluorene, 3-(
Examples include 9-fluorenylidene)-9-ethylcarbazole.
【００２７】化７で表わされる具体例としては、トリス
（４−ジエチルアミノフェニル）メタン、１，１−ビス
（４−ジベンジルアミノフェニル）プロパン、２，２’
−ジメチル−４，４’−ビス（ジエチルアミノ）−トリ
フェニルメタンなどがある。Specific examples of formula 7 include tris(4-diethylaminophenyl)methane, 1,1-bis(4-dibenzylaminophenyl)propane, 2,2'
-dimethyl-4,4'-bis(diethylamino)-triphenylmethane and the like.
【００２８】化８で表わされる具体例としては、１，２
−ビス（４−ジエチルアミノスチリル）ベンゼン、１，
２−ビス（２，４−ジメトキシスチリル）ベンゼンがあ
る。As a specific example represented by chemical formula 8, 1, 2
-bis(4-diethylaminostyryl)benzene, 1,
2-bis(2,4-dimethoxystyryl)benzene.
【００２９】化９で表わされる具体例としては、４’−
ジフェニルアミノ−α−フェニルスチルベン、４’−メ
チルフェニルアミノ−α−フェニルスチルベンなどがあ
る。As a specific example represented by chemical formula 9, 4'-
Examples include diphenylamino-α-phenylstilbene and 4'-methylphenylamino-α-phenylstilbene.
【００３０】化１０で表わされる具体例としては、３−
スチリル−９−エチルカルバゾール、３−（４−メトキ
シスチリル）−９−エチルカルバゾールなどがある。As a specific example represented by chemical formula 10, 3-
Examples include styryl-9-ethylcarbazole and 3-(4-methoxystyryl)-9-ethylcarbazole.
【００３１】化１１で表わされる具体例としては、４−
ジフェニルアミノスチルベン、４−ジベンジルアミノス
チルベン、４−ジトリルアミノスチルベン、１−（４−
ジフェニルアミノスチリル）ナフタレン、１−（４−ジ
エチルアミノスチリル）ナフタレンなどがある。As a specific example represented by chemical formula 11, 4-
Diphenylaminostilbene, 4-dibenzylaminostilbene, 4-ditolylaminostilbene, 1-(4-
Examples include diphenylaminostyryl) naphthalene and 1-(4-diethylaminostyryl) naphthalene.
【００３２】化１２で表わされる具体例としては、９−
（４−ジエチルアミノスチリル）アントラセン、９−ブ
ロム−１０−（４−ジエチルアミノスチリル）アントラ
センなどがある。As a specific example represented by chemical formula 12, 9-
(4-diethylaminostyryl)anthracene, 9-bromo-10-(4-diethylaminostyryl)anthracene, and the like.
【００３３】化１３で表わされる具体例としては、１−
フェニル−３−（４−ジエチルアミノスチリル）−５−
（４−ジエチルアミノフェニル）ピラゾリン、１−フェ
ニル−３−（４−ジメチルアミノスチリル）−５−（４
−ジメチルアミノフェニル）ピラゾリンなどがある。As a specific example represented by chemical formula 13, 1-
Phenyl-3-(4-diethylaminostyryl)-5-
(4-diethylaminophenyl)pyrazoline, 1-phenyl-3-(4-dimethylaminostyryl)-5-(4
-dimethylaminophenyl)pyrazoline, etc.
【００３４】これらの化合物は単独でも２種以上併用し
ても良い。正孔搬送物質と結着樹脂との重量比は１：９
９〜５０：５０であり、好ましくは１０：９０〜２０：
８０の範囲のとき所期の目的を達成することができる。
１：９９以下では残留電位低減の効果は無く、２０：８
０以上では機械的強度が劣化する。本発明の表面保護層
を形成するには金属又は金属酸化物粉末を結着樹脂溶液
中にボールミルあるいはビーズミルなどの方法で分散し
、次にこの分散液にたいし正孔搬送物質と結着樹脂との
重量比が１：９９〜５０：５０になるように上記正孔搬
送物質を添加し、これを光導電層上に浸漬・スプレーな
どの方法で塗布、乾燥、硬化させればよい。These compounds may be used alone or in combination of two or more. The weight ratio of hole transport substance and binder resin is 1:9
9-50:50, preferably 10:90-20:
When the value is in the range of 80, the desired purpose can be achieved. Below 1:99, there is no residual potential reduction effect, and 20:8
If it is 0 or more, mechanical strength deteriorates. To form the surface protective layer of the present invention, metal or metal oxide powder is dispersed in a binder resin solution using a method such as a ball mill or a bead mill, and then a hole transporting substance and a binder resin are added to this dispersion. The above-mentioned hole transporting substance may be added in a weight ratio of 1:99 to 50:50, and this may be applied onto the photoconductive layer by a method such as dipping or spraying, followed by drying and curing.
【００３５】本発明に用いられる金属あるいは金属酸化
物微粉末としては銅、スズ、アルミニウム、インジウム
等の金属あるいは酸化スズ、酸化亜鉛、酸化チタン、酸
化インジウム、酸化アンチモン、酸化ビスマス、アンチ
モンをドープした酸化スズ、スズをドープした酸化イン
ジウム等の金属酸化物微粉末を用いることができる。こ
れら金属あるいは金属酸化物微粉末は２種以上混合して
もかまわない。これら微粉末の平均粒径は０．５μｍ以
下好ましくは０．２μｍ以下にあることが保護層の透過
率の点から好ましい。The metal or metal oxide fine powder used in the present invention is doped with metals such as copper, tin, aluminum, and indium, or tin oxide, zinc oxide, titanium oxide, indium oxide, antimony oxide, bismuth oxide, and antimony. Metal oxide fine powder such as tin oxide or tin-doped indium oxide can be used. Two or more of these metal or metal oxide fine powders may be mixed. The average particle diameter of these fine powders is preferably 0.5 μm or less, preferably 0.2 μm or less, from the viewpoint of the transmittance of the protective layer.
【００３６】本発明に用いられる結着樹脂としては、シ
リコーン樹脂、ポリウレタン樹脂、アクリル樹脂、ポリ
エステル樹脂、ポリカーボネート樹脂、ポリスチレン樹
脂、エポキシ樹脂等が例示できる。なお、保護層中には
分散性、接着性あるいは平滑性を向上させる目的で種々
の添加剤を加えても良い。Examples of the binder resin used in the present invention include silicone resin, polyurethane resin, acrylic resin, polyester resin, polycarbonate resin, polystyrene resin, and epoxy resin. Note that various additives may be added to the protective layer for the purpose of improving dispersibility, adhesion, or smoothness.
【００３７】本発明に用いられる光導電層としてはＳｅ
、Ｓｅ−Ｔｅ、Ａｓ２Ｓｅ３等のＳｅ合金、ＺｎＯ、Ｃ
ｄＳ、ＣｄＳｅ等のＩＩ〜ＶＩ族化合物の粒子を樹脂に
分散させたもの、ポリビニルカルバゾール等の有機光導
電材料あるいはａ−Ｓｉ等が用いられる。光導電層の構
成は特に制約がなく、単層でも電荷発生層と電荷輸送層
の積層であってもかまわない。さらに保護層と光導電層
との間に密着性を高めるための接着層や電荷注入を阻止
するための電気的バリアー層を設けてもよい。The photoconductive layer used in the present invention is Se.
, Se-Te, Se alloys such as As2Se3, ZnO, C
Used are particles of II to VI group compounds such as dS and CdSe dispersed in resin, organic photoconductive materials such as polyvinylcarbazole, or a-Si. There are no particular restrictions on the structure of the photoconductive layer, and it may be a single layer or a stack of a charge generation layer and a charge transport layer. Further, an adhesive layer for increasing adhesion and an electrical barrier layer for preventing charge injection may be provided between the protective layer and the photoconductive layer.
【００３８】導電性支持体としては導電体あるいは導電
処理をした絶縁体が用いられる。たとえばＡｌ、Ｎｉ、
Ｆｅ、Ｃｕ、Ａｕなどの金属あるいは合金、ポリエステ
ル、ポリカーボネート、ポリイミド、ガラス等の絶縁性
基体上にＡｌ、Ａｇ、Ａｕ等の金属あるいはＩｎ２Ｏ３
、ＳｎＯ２等の導電材料の薄膜を形成したもの、導電処
理をした紙等が例示できる。また導電性支持体の形状は
特に制約はなく、必要に応じて板状、ドラム状、ベルト
状のものが用いられる。As the conductive support, a conductor or an insulator treated for conductivity is used. For example, Al, Ni,
Metals such as Fe, Cu, Au, etc. or alloys, polyester, polycarbonate, polyimide, glass, etc. on insulating substrates such as Al, Ag, Au, etc. or In2O3
Examples include those formed with a thin film of a conductive material such as SnO2, and paper treated with conductive treatment. Further, there are no particular restrictions on the shape of the conductive support, and plate-like, drum-like, or belt-like ones may be used as required.
【００３９】[0039]
【実施例】以下、本発明を実施例に従って説明する。
実施例１
８０ｍｍφ×３４０ｍｍ（長さ）のＡｌドラム支持体を
真空蒸着装置内にセットし、またこの装置の蒸着源ボー
トにＡｓ２Ｓｅ３合金を入れ、真空度３／１０６Ｔｏｒ
ｒ、支持体温度２００℃、ボート温度４５０℃の条件で
蒸着を行い、支持体上に６０μｍ厚の光導電層を形成し
た。次にこの上に、ａ）アルコキシ基含有ポリシロキサ
ンとｂ）水酸基含有ポリシロキサンとｃ）炭素原子に結
合したアミノ基、イミノ基又はニトリル基を少なくとも
１個及びアルコキシ基が２〜３個結合した珪素原子を有
する有機珪素化合物とを主成分とするシリコーン樹脂Ａ
（トーレシリコーン社製ＡＹ４２−４４０）と前記ａ）
、ｂ）及びｃ）の成分比が異なるシリコーン樹脂Ｂ（ト
ーレシリコーン社製ＡＹ４２−４４１）との等量（重量
）混合物のリグロイン溶液をスプレー塗布し、１２０℃
で１時間乾燥して０．１５μｍ厚の電気的バリアー層（
中間層）を形成した。次にＳｔ−ＭＭＡ−２−ＨＥＭＡ
共重合体の２０ｗｔ％酢酸２−エトキシエチル／メチル
イソブチルケトン（７／３重量比）溶液３０重量部と抵
抗制御剤ＳｎＯ２１４重量部とをボールミルで１２０時
間分散後、ヘキサメチレンジイソシアナート３重量部、
４−メトキシベンズアルデヒド１−メチル−１−フェニ
ルヒドラゾン０．９重量部を加えこれを電気的バリアー
層（中間層）上にスプレー塗布し、１３０℃で１時間の
乾燥を行い５μｍ厚の表面保護層を形成し、電子写真用
感光体を作製した。[Examples] The present invention will be explained below with reference to Examples. Example 1 An Al drum support of 80 mmφ x 340 mm (length) was set in a vacuum evaporation device, and As2Se3 alloy was put in the evaporation source boat of this device, and the vacuum degree was 3/106 Tor.
Vapor deposition was performed under the following conditions: r, support temperature 200° C., boat temperature 450° C., and a 60 μm thick photoconductive layer was formed on the support. Next, on top of this, a) a polysiloxane containing an alkoxy group, b) a polysiloxane containing a hydroxyl group, and c) at least one amino group, imino group, or nitrile group bonded to a carbon atom and 2 to 3 alkoxy groups bonded. Silicone resin A whose main component is an organic silicon compound having a silicon atom
(AY42-440 manufactured by Toray Silicone) and the above a)
A ligroin solution of an equal amount (by weight) mixture of silicone resin B (AY42-441 manufactured by Toray Silicone Co., Ltd.) having different component ratios of , b) and c) was spray applied, and the mixture was heated at 120°C.
to form a 0.15 μm thick electrical barrier layer (
intermediate layer) was formed. Next, St-MMA-2-HEMA
After dispersing 30 parts by weight of a 20 wt% copolymer solution of 2-ethoxyethyl acetate/methyl isobutyl ketone (7/3 weight ratio) and 214 parts by weight of the resistance control agent SnO in a ball mill for 120 hours, 3 parts by weight of hexamethylene diisocyanate was added. ,
Add 0.9 parts by weight of 4-methoxybenzaldehyde 1-methyl-1-phenylhydrazone and spray coat it onto the electrical barrier layer (intermediate layer), dry at 130°C for 1 hour to form a 5 μm thick surface protective layer. was formed to produce an electrophotographic photoreceptor.
【００４０】実施例２
前記正孔搬送物質を４−メトキシベンズアルデヒド１−
メチル−１−フェニルヒドラゾン０．０９重量部に変え
た他は実施例１と全く同様にして電子写真用感光体を作
製した。Example 2 The hole transport substance was 4-methoxybenzaldehyde 1-
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 0.09 parts by weight of methyl-1-phenylhydrazone was used.
【００４１】実施例３
前記正孔搬送物質を４−メトキシベンズアルデヒド１−
メチル−１−フェニルヒドラゾン９重量部に変えた他は
実施例１と全く同様にして電子写真用感光体を作製した
。Example 3 The hole transport substance was 4-methoxybenzaldehyde 1-
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 9 parts by weight of methyl-1-phenylhydrazone was used.
【００４２】実施例４
前記正孔搬送物質を４−ジメトキシベンズアルデヒド１
−ベンジル−１−フェニルヒドラゾン０．９重量部に変
えた他は実施例１と全く同様にして電子写真用感光体を
作製した。Example 4 The hole transport substance was 4-dimethoxybenzaldehyde 1
An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 0.9 parts by weight of -benzyl-1-phenylhydrazone was used.
【００４３】実施例５
前記正孔搬送物質を９−エチルカルバゾール−３−アル
デヒド１−メチル−１−フェニルヒドラゾン０．９重量
部に変えた他は実施例１と同様にして電子写真用感光体
を作製した。Example 5 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that the hole transporting substance was changed to 0.9 parts by weight of 9-ethylcarbazole-3-aldehyde 1-methyl-1-phenylhydrazone. was created.
【００４４】実施例６
前記正孔搬送物質を９−エチルカルバゾール−３−アル
デヒド１−メチル−１−フェニルヒドラゾン０．０９重
量部に変えた他は実施例１と全く同様にして電子写真感
光体を作製した。Example 6 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that the hole transport substance was changed to 0.09 parts by weight of 9-ethylcarbazole-3-aldehyde 1-methyl-1-phenylhydrazone. was created.
【００４５】実施例７
前記正孔搬送物質を９−エチルカルバゾール−３−アル
デヒド１−メチル−１−フェニルヒドラゾン９重量部に
変えた他は実施例１と全く同様にして電子写真用感光体
を作製した。Example 7 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 9 parts by weight of 9-ethylcarbazole-3-aldehyde 1-methyl-1-phenylhydrazone was used as the hole transport substance. Created.
【００４６】実施例８
前記正孔搬送物質を９−エチルカルバゾール−３−アル
デヒド １−ベンジル−１−フェニルヒドラゾン０．
９重量部に変えた他は実施例１と全く同様にして電子写
真用感光体を作製した。Example 8 The hole transport substance was 9-ethylcarbazole-3-aldehyde, 1-benzyl-1-phenylhydrazone, 0.
An electrophotographic photoreceptor was produced in the same manner as in Example 1 except that the amount was changed to 9 parts by weight.
【００４７】実施例９
前記搬送物質を４−メトキシナフタレン−１−アルデヒ
ド１−ベンジル−１−フェニルヒドラゾン０．９重量部
に変えた他は実施例１と全く同様にして電子写真用感光
体を作製した。Example 9 An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the carrier substance was changed to 0.9 parts by weight of 4-methoxynaphthalene-1-aldehyde-1-benzyl-1-phenylhydrazone. Created.
【００４８】実施例１０
前記正孔搬送物質を４−メトキシナフタレン−１−アル
デヒド １−ベンジル−１−フェニルヒドラゾン０．
０９重量部に変えた他は実施例１と全く同様にして電子
写真用感光体を作製した。Example 10 The hole transporting substance was 4-methoxynaphthalene-1-aldehyde, 1-benzyl-1-phenylhydrazone, 0.
An electrophotographic photoreceptor was produced in the same manner as in Example 1 except that the amount was changed to 0.09 parts by weight.
【００４９】実施例１１
前記正孔搬送物質を４−メトキシナフタレン−１−アル
デヒド １−ベンジル−１−フェニルヒドラゾン９重
量部に変えた他は実施例１と全く同様にして電子写真用
感光体を作製した。Example 11 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that the hole transport substance was changed to 9 parts by weight of 4-methoxynaphthalene-1-aldehyde 1-benzyl-1-phenylhydrazone. Created.
【００５０】実施例１２
前記正孔搬送物質を４−ジエチルアミノスチレン−β−
アルデヒド １−メチル−１−フェニルヒドラゾン０
．９重量部に変えた他は実施例１と全く同様にして電子
写真用感光体を作製した。Example 12 The hole transport substance was 4-diethylaminostyrene-β-
Aldehyde 1-methyl-1-phenylhydrazone 0
．． An electrophotographic photoreceptor was produced in the same manner as in Example 1 except that the amount was changed to 9 parts by weight.
【００５１】実施例１３
前記搬送物質を１−Ｎ，Ｎ−ビス（４−メチルフェニル
）アミノピレン０．９重量部に変えた他は実施例１と全
く同様にして電子写真用感光体を作製した。Example 13 An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the carrier substance was changed to 0.9 parts by weight of 1-N,N-bis(4-methylphenyl)aminopyrene. .
【００５２】実施例１４
前記正孔搬送物質を１−Ｎ，Ｎ−ビス（４−メチルフェ
ニル）アミノピレン０．０９重量部に変えた他は実施例
１と全く同様にして電子写真用感光体を作製した。Example 14 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 0.09 parts by weight of 1-N,N-bis(4-methylphenyl)aminopyrene was used as the hole transport substance. Created.
【００５３】実施例１５
前記正孔搬送物質を１−Ｎ，Ｎ−ビス（４−メチルフェ
ニル）アミノピレン９重量部に変えた他は実施例１と全
く同様にして電子写真用感光体を作製した。Example 15 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that the hole transport substance was changed to 9 parts by weight of 1-N,N-bis(4-methylphenyl)aminopyrene. .
【００５４】実施例１６
前記正孔搬送物質を１−Ｎ，Ｎ−ビス（３−メチルフェ
ニル）アミノピレン０．９重量部に変えた他は実施例１
と全く同様にして電子写真用感光体を作製した。Example 16 Example 1 except that the hole transport substance was changed to 0.9 parts by weight of 1-N,N-bis(3-methylphenyl)aminopyrene.
An electrophotographic photoreceptor was produced in exactly the same manner as described above.
【００５５】実施例１７
前記搬送物質をＮ，Ｎ−ジフェニル〔１，１’−ビフェ
ニル〕−４−アミン０．９重量部に変えた他は実施例１
と全く同様にして電子写真用感光体を作製した。Example 17 Example 1 except that the carrier substance was changed to 0.9 parts by weight of N,N-diphenyl[1,1'-biphenyl]-4-amine.
An electrophotographic photoreceptor was produced in exactly the same manner as described above.
【００５６】実施例１８
前記正孔搬送物質をＮ，Ｎ−ジフェニル〔１，１’−ビ
フェニル〕−４−アミン０．０９重量部に変えた他は実
施例１と全く同様にして電子写真用感光体を作製した。Example 18 A sample for electrophotography was prepared in the same manner as in Example 1 except that the hole transport substance was changed to 0.09 parts by weight of N,N-diphenyl[1,1'-biphenyl]-4-amine. A photoreceptor was produced.
【００５７】実施例１９
前記正孔搬送物質をＮ，Ｎ−ジフェニル〔１，１’−ビ
フェニル〕−４−アミン９重量部に変えた他は実施例１
と全く同様にして電子写真用感光体を作製した。Example 19 Example 1 except that the hole transport substance was changed to 9 parts by weight of N,N-diphenyl[1,1'-biphenyl]-4-amine.
An electrophotographic photoreceptor was produced in exactly the same manner as described above.
【００５８】実施例２０
前記正孔搬送物質をＮ，Ｎ−ビス（４−メチルフェニル
）−〔１，１’−ビフェニル〕−４−アミン０．９重量
部に変えた他は実施例１と全く同様にして電子写真用感
光体を作製した。Example 20 Same as Example 1 except that 0.9 parts by weight of N,N-bis(4-methylphenyl)-[1,1'-biphenyl]-4-amine was used as the hole transport substance. An electrophotographic photoreceptor was produced in exactly the same manner.
【００５９】実施例２１
前記搬送物質を９−（４−ジメチルアミノベンジリデン
）フルオレン０．９重量部に変えた他は実施例１と全く
同様にして電子写真用感光体を作製した。Example 21 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 0.9 parts by weight of 9-(4-dimethylaminobenzylidene)fluorene was used as the carrier substance.
【００６０】実施例２２
前記正孔搬送物質を９−（４−ジメチルアミノベンジリ
デン）フルオレン０．０９重量部に変えた他は実施例１
と全く同様にして電子写真用感光体を作製した。Example 22 Example 1 except that the hole transport substance was changed to 0.09 parts by weight of 9-(4-dimethylaminobenzylidene)fluorene.
An electrophotographic photoreceptor was produced in exactly the same manner as described above.
【００６１】実施例２３
前記正孔搬送物質を９−（４−ジメチルアミノベンジリ
デン）フルオレン９重量部に変えた他は実施例１と全く
同様にして電子写真用感光体を作製した。Example 23 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 9 parts by weight of 9-(4-dimethylaminobenzylidene)fluorene was used as the hole transport substance.
【００６２】実施例２４
前記正孔搬送物質を３−（９−フルオレニリデン）−９
−エチルカルバゾール０．９重量部に変えた他は実施例
１と全く同様にして電子写真用感光体を作製した。Example 24 The hole transport substance was 3-(9-fluorenylidene)-9
An electrophotographic photoreceptor was produced in the same manner as in Example 1 except that -ethylcarbazole was used in an amount of 0.9 parts by weight.
【００６３】実施例２５
前記搬送物質を１，１−ビス（４−ジベンジルアミノフ
ェニル）プロパン０．９重量部に変えた他は実施例１と
全く同様にして電子写真用感光体を作製した。Example 25 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that the carrier substance was changed to 0.9 parts by weight of 1,1-bis(4-dibenzylaminophenyl)propane. .
【００６４】実施例２６
前記正孔搬送物質を１，１−ビス（４−ジベンジルアミ
ノフェニル）プロパン０．０９重量部に変えた他は実施
例１と全く同様にして電子写真用感光体を作製した。Example 26 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 0.09 parts by weight of 1,1-bis(4-dibenzylaminophenyl)propane was used as the hole transport substance. Created.
【００６５】実施例２７
前記正孔搬送物質を１，１−ビス（４−ジベンジルアミ
ノフェニル）プロパン９重量部に変えた他は実施例１と
全く同様にして電子写真用感光体を作製した。Example 27 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that the hole transport substance was changed to 9 parts by weight of 1,1-bis(4-dibenzylaminophenyl)propane. .
【００６６】実施例２８
前記正孔搬送物質をトリス（４−ジエチルアミノフェニ
ル）メタン０．９重量部に変えた他は実施例１と全く同
様にして電子写真用感光体を作製した。Example 28 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 0.9 parts by weight of tris(4-diethylaminophenyl)methane was used as the hole transport substance.
【００６７】実施例２９
前記搬送物質を１，２−ビス（４−ジエチルアミノスチ
リル）ベンゼン０．９重量部に変えた他は実施例１と全
く同様にして電子写真用感光体を作製した。Example 29 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 0.9 parts by weight of 1,2-bis(4-diethylaminostyryl)benzene was used as the carrier substance.
【００６８】実施例３０
前記正孔搬送物質を１，２−ビス（４−ジエチルアミノ
スチリル）ベンゼン０．０９重量部に変えた他は実施例
１と全く同様にして電子写真用感光体を作製した。Example 30 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 0.09 parts by weight of 1,2-bis(4-diethylaminostyryl)benzene was used as the hole transport substance. .
【００６９】実施例３１
前記正孔搬送物質を１，２−ビス（４−ジエチルアミノ
スチリル）ベンゼン９重量部に変えた他は実施例１と全
く同様にして電子写真用感光体を作製した。Example 31 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 9 parts by weight of 1,2-bis(4-diethylaminostyryl)benzene was used as the hole transport substance.
【００７０】実施例３２
前記正孔搬送物質を１，２−ビス（２，４−ジメトキシ
スチリル）ベンゼン０．９重量部に変えた他は実施例１
と全く同様にして電子写真用感光体を作製した。Example 32 Example 1 except that the hole transport substance was changed to 0.9 parts by weight of 1,2-bis(2,4-dimethoxystyryl)benzene.
An electrophotographic photoreceptor was produced in exactly the same manner as described above.
【００７１】実施例３３
前記搬送物質を４’−ジフェニルアミノ−α−フェニル
スチルベン０．９重量部に変えた他は実施例１と全く同
様にして電子写真用感光体を作製した。Example 33 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 0.9 parts by weight of 4'-diphenylamino-α-phenylstilbene was used as the carrier substance.
【００７２】実施例３４
前記正孔搬送物質を４’−ジフェニルアミノ−α−フェ
ニルスチルベン０．０９重量部に変えた他は実施例１と
全く同様にして電子写真用感光体を作製した。Example 34 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 0.09 parts by weight of 4'-diphenylamino-α-phenylstilbene was used as the hole transport substance.
【００７３】実施例３５
前記正孔搬送物質を４’−ジフェニルアミノ−α−フェ
ニルスチルベン９重量部に変えた他は実施例１と全く同
様にして電子写真用感光体を作製した。Example 35 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 9 parts by weight of 4'-diphenylamino-α-phenylstilbene was used as the hole transport substance.
【００７４】実施例３６
前記正孔搬送物質を４’−メチルフェニルアミノ−α−
フェニルスチルベン０．９重量部に変えた他は実施例１
と全く同様にして電子写真用感光体を作製した。Example 36 The hole transport substance was 4'-methylphenylamino-α-
Example 1 except that phenylstilbene was changed to 0.9 parts by weight
An electrophotographic photoreceptor was produced in exactly the same manner as described above.
【００７５】実施例３７
前記搬送物質を３−スチリル−９−エチルカルバゾール
０．９重量部に変えた他は実施例１と全く同様にして電
子写真用感光体を作製した。Example 37 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 0.9 parts by weight of 3-styryl-9-ethylcarbazole was used as the carrier substance.
【００７６】実施例３８
前記正孔搬送物質を３−スチリル−９−エチルカルバゾ
ール０．０９重量部に変えた他は実施例１と全く同様に
して電子写真用感光体を作製した。Example 38 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 0.09 parts by weight of 3-styryl-9-ethylcarbazole was used as the hole transport substance.
【００７７】実施例３９
前記正孔搬送物質を３−スチリル−９−エチルカルバゾ
ール９重量部に変えた他は実施例１と全く同様にして電
子写真用感光体を作製した。Example 39 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 9 parts by weight of 3-styryl-9-ethylcarbazole was used as the hole transport substance.
【００７８】実施例４０
前記正孔搬送物質を３−（４−メトキシスチリル）−９
−エチルカルバゾール０．９重量部に変えた他は実施例
１と全く同様にして電子写真用感光体を作製した。Example 40 The hole transport substance was 3-(4-methoxystyryl)-9.
An electrophotographic photoreceptor was produced in the same manner as in Example 1 except that -ethylcarbazole was used in an amount of 0.9 parts by weight.
【００７９】実施例４１
前記正孔搬送物質４−ジフェニルアミノスチルベンを０
．９重量部に変えた他は実施例１と全く同様にして電子
写真用感光体を作製した。Example 41 The hole transport substance 4-diphenylaminostilbene was added to 0
．． An electrophotographic photoreceptor was produced in the same manner as in Example 1 except that the amount was changed to 9 parts by weight.
【００８０】実施例４２
前記正孔搬送物質を４−ジフェニルアミノスチルベン０
．０９重量部に変えた他は実施例１と全く同様にして電
子写真用感光体を作製した。Example 42 The hole transport substance was 4-diphenylaminostilbene.
．． An electrophotographic photoreceptor was produced in the same manner as in Example 1 except that the amount was changed to 0.09 parts by weight.
【００８１】実施例４３
前記正孔搬送物質を４−ジフェニルアミノスチルベン９
重量部に変えた他は実施例１と全く同様にして電子写真
用感光体を作製した。Example 43 The hole transport substance was 4-diphenylaminostilbene 9
An electrophotographic photoreceptor was produced in exactly the same manner as in Example 1 except that the parts by weight were changed.
【００８２】実施例４４
前記正孔搬送物質を４−ジフェニルアミノスチルベン０
．９重量部に変えた他は実施例１と全く同様にして電子
写真用感光体を作製した。Example 44 The hole transport substance was 4-diphenylaminostilbene.
．． An electrophotographic photoreceptor was produced in the same manner as in Example 1 except that the amount was changed to 9 parts by weight.
【００８３】実施例４５
前記搬送物質を９−（４−ジエチルアミノスチリル）ア
ントラセン０．９重量部に変えた他は実施例１と全く同
様にして電子写真用感光体を作製した。Example 45 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 0.9 parts by weight of 9-(4-diethylaminostyryl)anthracene was used as the carrier substance.
【００８４】実施例４６
前記正孔搬送物質を９−（４−ジエチルアミノスチリル
）アントラセン０．０９重量部に変えた他は実施例１と
全く同様にして電子写真用感光体を作製した。Example 46 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 0.09 parts by weight of 9-(4-diethylaminostyryl)anthracene was used as the hole transport substance.
【００８５】実施例４７
前記正孔搬送物質を９−（４−ジエチルアミノスチリル
）アントラセン９重量部に変えた他は実施例１と全く同
様にして電子写真用感光体を作製した。Example 47 An electrophotographic photoreceptor was prepared in the same manner as in Example 1 except that 9 parts by weight of 9-(4-diethylaminostyryl)anthracene was used as the hole transport substance.
【００８６】実施例４８
前記正孔搬送物質を９−ブロム−１０−（４−ジエチル
アミノスチリル）アントラセン０．９重量部に変えた他
は実施例１と全く同様にして電子写真用感光体を作製し
た。Example 48 An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that 0.9 parts by weight of 9-bromo-10-(4-diethylaminostyryl)anthracene was used as the hole transport substance. did.
【００８７】実施例４９
前記搬送物質を１−フェニル−３−（４−ジエチルアミ
ノスチリル）−５−（４−ジエチルアミノフェニル）ピ
ラゾリン０．９重量部に変えた他は実施例１と全く同様
にして電子写真用感光体を作製した。Example 49 The same procedure as in Example 1 was carried out except that the carrier substance was changed to 0.9 parts by weight of 1-phenyl-3-(4-diethylaminostyryl)-5-(4-diethylaminophenyl)pyrazoline. A photoreceptor for electrophotography was produced.
【００８８】実施例５０
前記正孔搬送物質を１−フェニル−３−（４−ジエチル
アミノスチリル）−５−（４−ジエチルアミノフェニル
）ピラゾリン０．０９重量部に変えた他は実施例１と全
く同様にして電子写真用感光体を作製した。Example 50 Completely the same as Example 1 except that the hole transport substance was changed to 0.09 parts by weight of 1-phenyl-3-(4-diethylaminostyryl)-5-(4-diethylaminophenyl)pyrazoline. An electrophotographic photoreceptor was produced.
【００８９】実施例５１
前記正孔搬送物質を１−フェニル−３−（４−ジエチル
アミノスチリル）−５−（４−ジエチルアミノフェニル
）ピラゾリン９重量部に変えた他は実施例１と全く同様
にして電子写真用感光体を作製した。Example 51 The same procedure as in Example 1 was carried out except that the hole transport substance was changed to 9 parts by weight of 1-phenyl-3-(4-diethylaminostyryl)-5-(4-diethylaminophenyl)pyrazoline. A photoreceptor for electrophotography was manufactured.
【００９０】実施例５２
前記正孔搬送物質を１−フェニル−３−（４−ジメチル
アミノスチリル）−５−（４−ジメチルアミノフェニル
）ピラゾリン０．９重量部に変えた他は実施例１と全く
同様にして電子写真用感光体を作製した。Example 52 Same as Example 1 except that the hole transport substance was changed to 0.9 parts by weight of 1-phenyl-3-(4-dimethylaminostyryl)-5-(4-dimethylaminophenyl)pyrazoline. An electrophotographic photoreceptor was produced in exactly the same manner.
【００９１】比較例
前記正孔搬送物質を加えない他は実施例１と全く同様に
して電子写真用感光体を作製した。Comparative Example An electrophotographic photoreceptor was prepared in exactly the same manner as in Example 1, except that the hole transport substance was not added.
【００９２】上記のようにして得た電子写真用感光体に
対して、リコー製複写機ＦＴ６５５０を用いて，２０℃
６５％及び１０℃１５％の環境下での複写機内の残留電
位を評価し、更に１０万枚の画像テストを行い、画像テ
スト前後の保護層の膜厚測定を実施しその摩耗量の評価
を行った。評価結果を表１に示す。The electrophotographic photoreceptor obtained as described above was heated at 20° C. using a Ricoh copier FT6550.
We evaluated the residual potential inside the copying machine under the conditions of 65% and 10°C and 15%, conducted an image test of 100,000 sheets, measured the thickness of the protective layer before and after the image test, and evaluated the amount of wear. went. The evaluation results are shown in Table 1.
【００９３】[0093]
【表１−（１）】[Table 1-(1)]
【００９４】[0094]
【表１−（２）】[Table 1-(2)]
【００９５】[0095]
【表１−（３）】[Table 1-(3)]
【００９６】[0096]
【表１−（４）】[Table 1-(4)]
【００９７】表１に示されるように、本発明に係る実施
例１〜５２の電子写真用感光体は２０℃６５％及び１０
℃１５％下での残留電位が大きく低減されており、更に
正孔搬送物質と結着樹脂との重量比が１：９９〜５０：
５０の範囲にあるので１０万枚複写後の表面保護層の膜
厚減少量も著しく小さいことがわかる。また、実施例１
〜５２の電子写真用感光体は初期から１０万枚後まで品
質の高い画像が安定して継続的に得られるものであった
。As shown in Table 1, the electrophotographic photoreceptors of Examples 1 to 52 according to the present invention were heated at 20°C, 65% and 10°C.
The residual potential at 15% °C is greatly reduced, and the weight ratio of the hole transport substance to the binder resin is 1:99 to 50:
50, it can be seen that the amount of decrease in the thickness of the surface protective layer after copying 100,000 sheets is also extremely small. In addition, Example 1
With the electrophotographic photoreceptors No. 52 to 10, high-quality images could be stably and continuously obtained from the initial stage until after 100,000 sheets were printed.
【００９８】[0098]
【発明の効果】以上説明したように、本発明に係る表面
保護層を有する電子写真用感光体は高い機械的強度をそ
なえ、かつ複写機内の残留電位及びその環境変動量も著
しく小さい安定した電気特性を示し、更に高品質な画像
が長期に渡って安定して得られる信頼性の高いものであ
る。Effects of the Invention As explained above, the electrophotographic photoreceptor having the surface protective layer according to the present invention has high mechanical strength, and has a stable electric potential with extremely small residual potential inside the copying machine and extremely small environmental fluctuations. It is a highly reliable product that exhibits characteristics and can stably obtain high-quality images over a long period of time.
Claims (12)
護層を順次積層した電子写真用感光体において、表面保
護層が金属あるいは金属酸化物微粉末を結着樹脂中に分
散させた層からなり、かつ正孔搬送物質を含有させたこ
とを特徴とする電子写真用感光体。Claim 1: In an electrophotographic photoreceptor in which a photoconductive layer and a surface protective layer are sequentially laminated on a conductive support, the surface protective layer is a layer in which metal or metal oxide fine powder is dispersed in a binder resin. What is claimed is: 1. An electrophotographic photoreceptor comprising:
れる化合物を含有させたことを特徴とする請求項１記載
の電子写真用感光体。 【化１】 〔式中、Ｒ１はアルキル基、ベンジル基、フェニル基を
表わし、Ｒ２は水素、炭素数１〜３のアルキル基、炭素
数１〜３のアルコキシ基、ジアルキルアミノ基、ジアラ
ルキルアミノ基またはジアリールアミノ基を表わし、ｎ
は１〜４の整数を表わし、ｎが２以上のときＲ２は同じ
でも異なっていてもよい。Ｒ３は水素またはメトキシ基
を表わす。〕2. The electrophotographic photoreceptor according to claim 1, further comprising a compound represented by the following chemical formula 1 as a hole transporting substance. [Formula 1] [In the formula, R1 represents an alkyl group, a benzyl group, or a phenyl group, and R2 represents hydrogen, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a dialkylamino group, or a dialkylamino group. group or diarylamino group, n
represents an integer of 1 to 4, and when n is 2 or more, R2 may be the same or different. R3 represents hydrogen or a methoxy group. ]
れる化合物を含有させたことを特徴とする請求項１記載
の電子写真用感光体。 【化２】 〔式中、Ｒ１はメチル基、エチル基、２−ヒドロキシエ
チル基又は２−クロルエチル基を表わし、Ｒ２はメチル
基、エチル基、ベンジル基又はフェニル基を表わし、Ｒ
３は水素、塩素、臭素、炭素数１〜４のアルキル基、炭
素数１〜４のアルコキシ基、ジアルキルアミノ基又はニ
トロ基を表わす。〕3. The electrophotographic photoreceptor according to claim 1, which contains a compound represented by the following chemical formula 2 as a hole transporting substance. [Formula, R1 represents a methyl group, ethyl group, 2-hydroxyethyl group or 2-chloroethyl group, R2 represents a methyl group, ethyl group, benzyl group or phenyl group, R
3 represents hydrogen, chlorine, bromine, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a dialkylamino group, or a nitro group. ]
れる化合物を含有させたことを特徴とする請求項１記載
の電子写真用感光体。 【化３】 〔式中、Ａｒはナフタリン環、アントラセン環、スチリ
ル基及びそれらの置換体あるいはピリジン環、フラン環
、チオフェン環を表わし、Ｒはアルキル基又はベンジル
基を表わす。〕4. The electrophotographic photoreceptor according to claim 1, which contains a compound represented by the following chemical formula 3 as a hole transporting substance. embedded image [In the formula, Ar represents a naphthalene ring, an anthracene ring, a styryl group, or a substituted product thereof, or a pyridine ring, a furan ring, or a thiophene ring, and R represents an alkyl group or a benzyl group. ]
れる化合物を含有させたことを特徴とする請求項１記載
の電子写真用感光体。 【化４】 〔式中、Ａ１，Ａ２は置換もしくは無置換のアルキル基
又は置換もしくは無置換のアリール基を表わし、それぞ
れ同一でも異なっていてもよい。Ａｒは置換または無置
換の縮合多環式炭化水素基を表わす。〕5. The electrophotographic photoreceptor according to claim 1, which contains a compound represented by the following chemical formula 4 as a hole transporting substance. embedded image [In the formula, A1 and A2 represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and may be the same or different. Ar represents a substituted or unsubstituted condensed polycyclic hydrocarbon group. ]
れる化合物を含有させたことを特徴とする請求項１記載
の電子写真用感光体。 【化５】 〔式中、Ｒ１，Ｒ３及びＲ４は水素原子、アミノ基、ア
ルコキシ基、チオアルコキシ基、アリールオキシ基、メ
チレンジオキシ基、置換もしくは無置換のアルキル基、
ハロゲン原子又は置換もしくは無置換のアリール基を、
Ｒ２は水素原子、アルコキシ基、置換もしくは無置換の
アルキル基又はハロゲンを表わす。ｋは１〜５の整数、
ｌは１〜４の整数、ｍは１〜５の整数、ｎは１〜５の整
数である。〕6. The electrophotographic photoreceptor according to claim 1, which contains a compound represented by the following chemical formula 5 as a hole transporting substance. [Formula 5, R1, R3 and R4 are hydrogen atoms, amino groups, alkoxy groups, thioalkoxy groups, aryloxy groups, methylenedioxy groups, substituted or unsubstituted alkyl groups,
A halogen atom or a substituted or unsubstituted aryl group,
R2 represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group, or a halogen. k is an integer from 1 to 5,
l is an integer of 1 to 4, m is an integer of 1 to 5, and n is an integer of 1 to 5. ]
れる化合物を含有させたことを特徴とする請求項１記載
の電子写真用感光体。 【化６】 〔式中Ｒ１は水素、ハロゲン、シアノ基、炭素数１〜４
のアルコキシ基または炭素数１〜４のアルキル基を表わ
し、Ａｒは Ｒ２は炭素数１〜４のアルキル基を表わし、Ｒ３は水素
、ハロゲン、炭素数１〜４のアルキル基、炭素数１〜４
のアルコキシ基またはジアルキルアミノ基を表わし、ｎ
は１または２であって、ｎが２のときはＲ３は同一でも
異なってもよく、Ｒ４およびＲ５は水素、炭素数１〜４
の置換または無置換のアルキル基あるいは置換または無
置換のベンジル基を表わす。〕7. The electrophotographic photoreceptor according to claim 1, which contains a compound represented by the following chemical formula 6 as a hole transporting substance. [Formula R1 is hydrogen, halogen, cyano group, carbon number 1-4
represents an alkoxy group or an alkyl group having 1 to 4 carbon atoms, Ar is R2 represents an alkyl group having 1 to 4 carbon atoms, and R3 is hydrogen, halogen, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms.
represents an alkoxy group or dialkylamino group, n
is 1 or 2, and when n is 2, R3 may be the same or different, R4 and R5 are hydrogen, and have 1 to 4 carbon atoms.
represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted benzyl group. ]
れる化合物を含有させたことを特徴とする請求項１記載
の電子写真用感光体。 【化７】 〔式中、Ｒ１は炭素数１〜１１のアルキル基、置換もし
くは無置換のフェニル基又は複素環基を表わし、Ｒ２，
Ｒ３はそれぞれ同一でも異なっていてもよく水素、炭素
数１〜４のアルキル基、ヒドロキシアルキル基、クロル
アルキル基、置換または無置換のアラルキル基を表わし
、また、Ｒ２とＲ３は互いに結合し窒素を含む複素環を
形成していてもよい。Ｒ４は同一でも異なっていてもよ
く水素、炭素数１〜４のアルキル基、アルコキシ基又は
ハロゲンを表わす。〕8. The electrophotographic photoreceptor according to claim 1, which contains a compound represented by the following chemical formula 7 as a hole transporting substance. [In the formula, R1 represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group, or a heterocyclic group, R2,
R3 may be the same or different and each represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group, a chloroalkyl group, a substituted or unsubstituted aralkyl group, and R2 and R3 are bonded to each other and represent nitrogen. may form a heterocycle containing. R4 may be the same or different and represents hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group, or a halogen. ]
れる化合物を含有させたことを特徴とする請求項１記載
の電子写真用感光体。 【化８】 〔式中、Ｒはカルバゾリル基、ピリジル基、チエニル基
、インドリル基、フリル基或いはそれぞれ置換もしくは
無置換のフェニル基、スチリル基、ナフチル基またはア
ントリル基であって、これらの置換基がジアルキルアミ
ノ基、アルキル基、アルコキシ基、カルボキシ基または
そのエステル、ハロゲン原子、シアノ基、アラルキルア
ミノ基、Ｎ−アルキル−Ｎ−アラルキルアミノ基、アミ
ノ基、ニトロ基およびアセチルアミノ基からなる群から
選ばれた基を表わす。〕9. The electrophotographic photoreceptor according to claim 1, which contains a compound represented by the following formula 8 as a hole transporting substance. [Formula 8] [In the formula, R is a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group, or an anthryl group, and these substituents is from the group consisting of a dialkylamino group, an alkyl group, an alkoxy group, a carboxy group or an ester thereof, a halogen atom, a cyano group, an aralkylamino group, an N-alkyl-N-aralkyl amino group, an amino group, a nitro group, and an acetylamino group Represents the selected group. ]
される化合物を含有させたことを特徴とする請求項１記
載の電子写真用感光体。 【化９】 〔式中、ｎは０または１の整数、Ｒ１は水素原子、アル
キル基または置換もしくは無置換のフェニル基を示し、
Ａは ９−アントリル基または置換もしくは無置換のＮ−アル
キルカルバゾリル基を表わし、ここでＲ２は水素原子、
アルキル基、アルコキシ基、ハロゲン原子または（但し
、Ｒ３およびＲ４はアルキル基、置換または無置換のア
ラルキル基、置換または無置換のアリール基を示し、Ｒ
３およびＲ４は環を形成してもよい）を表わし、ｍは０
，１，２または３の整数であって、ｍが２以上のときは
Ｒ２は同一でも異なってもよい。〕10. The electrophotographic photoreceptor according to claim 1, which contains a compound represented by the following chemical formula 9 as a hole transporting substance. [In the formula, n is an integer of 0 or 1, R1 represents a hydrogen atom, an alkyl group, or a substituted or unsubstituted phenyl group,
A represents a 9-anthryl group or a substituted or unsubstituted N-alkylcarbazolyl group, where R2 is a hydrogen atom,
an alkyl group, an alkoxy group, a halogen atom or (where R3 and R4 represent an alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group,
3 and R4 may form a ring), m is 0
, 1, 2 or 3, and when m is 2 or more, R2 may be the same or different. ]
正孔搬送物質として、下記化１０で示される化合物を含
有させたことを特徴とする請求項１記載の電子写真用感
光体。 【化１０】 〔式中、Ｒ１は低級アルキル基またはベンジル基を表わ
し、Ｒ２は水素原子、低級アルキル基、低級アルコキシ
基、ハロゲン原子、ニトロ基、アミノ基あるいは低級ア
ルキル基またはベンジル基で置換されたアミノ基を表わ
し、ｎは１または２の整数を表わす。〕[Claim 11]
2. The electrophotographic photoreceptor according to claim 1, further comprising a compound represented by the following formula 10 as a hole transporting substance. [In the formula, R1 represents a lower alkyl group or a benzyl group, and R2 is substituted with a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, an amino group, a lower alkyl group, or a benzyl group] represents an amino group, and n represents an integer of 1 or 2. ]
正孔搬送物質として、下記化１１で示される化合物
を含有させたことを特徴とする請求項１記載の電子写真
用感光体。 【化１１】 〔式中、Ｒ１は水素原子、アルキル基、アルコキシ基ま
たはハロゲン原子を表わし、Ｒ２およびＲ３はアルキル
基、置換または無置換のアラルキル基あるいは置換また
は無置換のアリール基を表わし、Ｒ４は水素原子または
置換もしくは無置換のフェニル基を表わし、また、Ａｒ
はフェニル基またはナフチル基を表わす。〕【請求項１
３】 正孔搬送物質として、下記化１２で示される化
合物を含有させたことを特徴とする請求項１記載の電子
写真用感光体。 【化１２】 〔式中、Ｒは水素またはハロゲン原子を表わし、Ａｒは
置換または無置換のフェニル基、ナフチル基、アントリ
ル基あるいはカルバゾリル基を表わす。〕【請求項１４
】 正孔搬送物質として、下記化１３で示される化合
物を含有させたことを特徴とする請求項１記載の電子写
真用感光体。 【化１３】 〔式中、Ｒ１，Ｒ２およびＲ３は水素、低級アルキル基
、低級アルコキシ基、ジアルキルアミノ基またはハロゲ
ン原子を表わし、ｎは０または１を表わす。〕【請求項
１５】 正孔搬送物質と結着樹脂との重量比が１：９
９〜５０：５０であることを特徴とする請求項１ないし
１４のいずれかに記載された電子写真用感光体。[Claim 12]
2. The electrophotographic photoreceptor according to claim 1, further comprising a compound represented by the following chemical formula 11 as a hole transporting substance. [In the formula, R1 represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, R2 and R3 represent an alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, and R4 represents a hydrogen atom or a substituted or unsubstituted phenyl group, and Ar
represents a phenyl group or a naphthyl group. ] [Claim 1
3. The electrophotographic photoreceptor according to claim 1, which contains a compound represented by the following chemical formula 12 as a hole transporting substance. embedded image [In the formula, R represents hydrogen or a halogen atom, and Ar represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group, or carbazolyl group. ] [Claim 14
10. The electrophotographic photoreceptor according to claim 1, further comprising a compound represented by the following chemical formula 13 as a hole transporting substance. embedded image [In the formula, R1, R2 and R3 represent hydrogen, a lower alkyl group, a lower alkoxy group, a dialkylamino group or a halogen atom, and n represents 0 or 1. [Claim 15] The weight ratio of the hole transport substance and the binder resin is 1:9.
15. The electrophotographic photoreceptor according to claim 1, wherein the ratio is 9 to 50:50.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06906691A JP3286711B2 (en) | 1991-03-08 | 1991-03-08 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06906691A JP3286711B2 (en) | 1991-03-08 | 1991-03-08 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04281461A true JPH04281461A (en) | 1992-10-07 |
| JP3286711B2 JP3286711B2 (en) | 2002-05-27 |
Family
ID=13391832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP06906691A Expired - Lifetime JP3286711B2 (en) | 1991-03-08 | 1991-03-08 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3286711B2 (en) |
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1991
- 1991-03-08 JP JP06906691A patent/JP3286711B2/en not_active Expired - Lifetime
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