JPH08100038A - Triphenylamine polymer, its production, and use thereof - Google Patents
Triphenylamine polymer, its production, and use thereofInfo
- Publication number
- JPH08100038A JPH08100038A JP7171739A JP17173995A JPH08100038A JP H08100038 A JPH08100038 A JP H08100038A JP 7171739 A JP7171739 A JP 7171739A JP 17173995 A JP17173995 A JP 17173995A JP H08100038 A JPH08100038 A JP H08100038A
- Authority
- JP
- Japan
- Prior art keywords
- layer
- organic
- hole transport
- compound
- substituted
- 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
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229920000642 polymer Polymers 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000000463 material Substances 0.000 claims abstract description 72
- 230000005525 hole transport Effects 0.000 claims abstract description 35
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 7
- 238000005401 electroluminescence Methods 0.000 claims description 39
- 108091008695 photoreceptors Proteins 0.000 claims description 21
- -1 triphenylamine compound Chemical class 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract description 12
- 229940098779 methanesulfonic acid Drugs 0.000 abstract description 6
- 239000003377 acid catalyst Substances 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 107
- 150000001875 compounds Chemical class 0.000 description 49
- 239000010408 film Substances 0.000 description 29
- 238000002347 injection Methods 0.000 description 25
- 239000007924 injection Substances 0.000 description 25
- 238000000034 method Methods 0.000 description 21
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000758 substrate Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 4
- 229920005668 polycarbonate resin Polymers 0.000 description 4
- 239000004431 polycarbonate resin Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000004544 sputter deposition Methods 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000013365 molecular weight analysis method Methods 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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
- 229920000548 poly(silane) polymer Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910000861 Mg alloy Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 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
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 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
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920001230 polyarylate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000000746 purification Methods 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
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000006617 triphenylamine group Chemical group 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 description 1
- GUPMCMZMDAGSPF-UHFFFAOYSA-N 1-phenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1[C](C=C[CH2])C1=CC=CC=C1 GUPMCMZMDAGSPF-UHFFFAOYSA-N 0.000 description 1
- NIDFGXDXQKPZMA-UHFFFAOYSA-N 14h-benz[4,5]isoquino[2,1-a]perimidin-14-one Chemical compound C1=CC(N2C(=O)C=3C4=C(C2=N2)C=CC=C4C=CC=3)=C3C2=CC=CC3=C1 NIDFGXDXQKPZMA-UHFFFAOYSA-N 0.000 description 1
- NQRACBRRMUBSDA-UHFFFAOYSA-N 17-azahexacyclo[10.9.2.02,7.03,19.08,23.015,22]tricosa-1(21),2(7),3,5,8,10,12(23),13,15(22),19-decaene-16,18-dione Chemical compound C12=CC=C3C=CC=C4C5=CC=CC=6C(=CC=C(C1=C34)C56)C(NC2=O)=O NQRACBRRMUBSDA-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- HVTQDSGGHBWVTR-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-phenylmethoxypyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound C(C1=CC=CC=C1)OC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CCOCC1 HVTQDSGGHBWVTR-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- KIGTXAWIOISJOG-UHFFFAOYSA-N 4-methoxy-n,n-diphenylaniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 KIGTXAWIOISJOG-UHFFFAOYSA-N 0.000 description 1
- IULUNTXBHHKFFR-UHFFFAOYSA-N 4-methyl-n,n-diphenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 IULUNTXBHHKFFR-UHFFFAOYSA-N 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- VESMRDNBVZOIEN-UHFFFAOYSA-N 9h-carbazole-1,2-diamine Chemical compound C1=CC=C2C3=CC=C(N)C(N)=C3NC2=C1 VESMRDNBVZOIEN-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910001370 Se alloy Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229910001215 Te alloy Inorganic materials 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
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- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
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- 239000011230 binding agent Substances 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- 238000007598 dipping method Methods 0.000 description 1
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
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- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
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- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000003550 marker Substances 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ASZIMSKBYDBAOJ-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]-2-methylaniline Chemical compound CC1=CC=CC=C1NC1=CC=C(C=2C=CC(N)=CC=2)C=C1 ASZIMSKBYDBAOJ-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920002382 photo conductive polymer Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
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- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
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- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
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- 239000011241 protective layer Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Landscapes
- Photoreceptors In Electrophotography (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明はトリフェニルアミン
構造を有する正孔輸送材料に関し、該トリフェニルアミ
ン重合体は、感光材料、有機光導電材料として使用で
き、さらに具体的には、平面光源や表示に使用される有
機エレクトロルミネッセンス（ＥＬ）素子もしくは電子
写真感光体等の正孔輸送材料として利用できる。TECHNICAL FIELD The present invention relates to a hole transporting material having a triphenylamine structure, and the triphenylamine polymer can be used as a photosensitive material or an organic photoconductive material. It can be used as a hole transport material for an organic electroluminescence (EL) element or an electrophotographic photoreceptor used for display.
【０００２】[0002]
【従来の技術】感光材料や正孔輸送材料として開発され
ている有機光導電材料は、低コスト、加工性が多様であ
り、無公害性などの多くの利点があり、多くの化合物が
提案されている。例えば、オキサジアゾール誘導体（米
国特許第３，１８９，４４７号）、オキサゾール誘導体
（米国特許第３，２５７，２０３号）、ヒドラゾン誘導
体（米国特許第３，７１７，４６２号、特開昭５４−５
９，１４３号、米国特許第４，１５０，９７８号）、ト
リアリールピラゾリン誘導体（米国特許第３，８２０，
９８９号、特開昭５１−９３，２２４号、特開昭５５−
１０８，６６７号）、アリールアミン誘導体（米国特許
第３，１８０，７３０号、米国特許第４，２３２，１０
３号、特開昭５５−１４４，２５０号、特開昭５６−１
１９，１３２号）、スチルベン誘導体（特開昭５８−１
９０，９５３号、特開昭５９−１９５，６５８号）など
の有機光導電性材料が開示されている。2. Description of the Related Art Organic photoconductive materials which have been developed as photosensitive materials and hole transport materials have many advantages such as low cost, various processability and no pollution, and many compounds have been proposed. ing. For example, oxadiazole derivatives (U.S. Pat. No. 3,189,447), oxazole derivatives (U.S. Pat. No. 3,257,203), hydrazone derivatives (U.S. Pat. No. 3,717,462, JP-A-54- 5
9,143, US Pat. No. 4,150,978), triarylpyrazoline derivatives (US Pat. No. 3,820,
989, JP-A-51-93,224, JP-A-55-
108,667), arylamine derivatives (US Pat. No. 3,180,730, US Pat. No. 4,232,10).
3, JP-A-55-144,250, and JP-A-56-1.
19,132), stilbene derivatives (JP-A-58-1)
No. 90,953, JP-A-59-195,658) and other organic photoconductive materials are disclosed.
【０００３】正孔輸送材料を利用した技術の一つとして
は、有機ＥＬ素子が挙げられる。有機物質を使用したＥ
Ｌ素子は、固体発光型の安価な大面積フルカラー表示素
子としての用途が有望視され、多くの開発が行われてい
る。一般にＥＬは発光層および該層をはさんだ一対の対
向電極から構成されている。発光は、両電極間に電界が
印加されると、陰極側から電子が注入され、陽極側から
正孔が注入される。さらに、この電子が発光層において
正孔と再結合し、エネルギー準位が伝導帯から価電子帯
に戻る際にエネルギーを光として放出する現象である。As one of the technologies utilizing the hole transport material, there is an organic EL element. E using organic substances
The L element is promising for use as a solid-state light emitting inexpensive large area full color display element, and many developments have been made. Generally, an EL is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, this is a phenomenon in which the electrons are recombined with holes in the light emitting layer, and energy is emitted as light when the energy level returns from the conduction band to the valence band.
【０００４】従来の有機ＥＬ素子は、無機ＥＬ素子に比
べて駆動電圧が高く、発光輝度や発光効率も低かった。
また、特性劣化も著しく実用化には至っていなかった。
近年、１０Ｖ以下の低電圧で発光する高い蛍光量子効率
を持った有機化合物を含有した薄膜を積層した有機ＥＬ
素子が報告され、関心を集めている（アプライド・フィ
ジクス・レターズ、５１巻、９１３ページ、１９８７年
参照）。この方法は、金属キレート錯体を蛍光体層、ア
ミン系化合物を正孔注入層に使用して、高輝度の緑色発
光を得ており、６〜７Ｖの直流電圧で輝度は数１００ｃ
ｄ／ｍ2、最大発光効率は１．５ｌｍ／Ｗを達成して、
実用領域に近い性能を持っている。The conventional organic EL element has a higher driving voltage and lower emission brightness and emission efficiency than the inorganic EL element.
In addition, the deterioration of the characteristics was remarkable and it was not put to practical use.
2. Description of the Related Art In recent years, an organic EL in which a thin film containing an organic compound having high fluorescence quantum efficiency that emits light at a low voltage of 10 V or less is laminated.
The device has been reported and is of great interest (see Applied Physics Letters, 51, 913, 1987). This method uses a metal chelate complex for a phosphor layer and an amine compound for a hole injecting layer to obtain high-intensity green light emission, and a direct current voltage of 6 to 7 V produces an intensity of several 100 c.
d / m 2 , maximum luminous efficiency of 1.5 lm / W is achieved,
It has the performance close to the practical range.
【０００５】しかしながら、現在までの有機ＥＬ素子
は、構成の改善により発光強度は改良されているが、未
だ充分な発光輝度は有していない。また、繰り返し使用
時の安定性に劣るという大きな問題を持っている。従っ
て、より大きな発光輝度を持ち、繰り返し使用時での安
定性の優れた有機ＥＬ素子の開発のために、優れた正孔
輸送能力を有し、耐久性のある正孔輸送材料の開発が望
まれている。However, although the organic EL devices to date have been improved in the emission intensity due to the improved structure, they still do not have sufficient emission brightness. Further, it has a big problem that it is inferior in stability when repeatedly used. Therefore, in order to develop an organic EL device having higher emission brightness and excellent stability in repeated use, it is desired to develop a hole transport material having excellent hole transport ability and durability. It is rare.
【０００６】さらに、正孔輸送材料を利用した技術とし
ては、電子写真感光体が挙げられる。電子写真方式は、
カールソンにより発明された画像形成法の一つである。
この方式は、コロナ放電により感光体を帯電した後、光
像露光して感光体に静電潜像を得、該静電潜像にトナー
を付着させて現像し、得られたトナー像を紙へ転写する
ことからなる。このような電子写真方式における感光体
に要求される基本的な特性としては、暗所において適当
な電位が保持されること、暗所における電荷の放電が少
ないこと、光照射により速やかに電荷を放電することな
どが挙げられる。従来までの電子写真感光体は、セレ
ン、セレン合金、酸化亜鉛、硫化カドミウムおよびテル
ルなどの無機光導電体が使用されてきた。これらの無機
光導電体は、耐久性が高く、耐刷枚数が多いなどの利点
を有しているが、製造コストが高く、加工性が劣り、毒
性を有するなどの問題点が指摘されている。これらの欠
点を克服するために有機感光体の開発が行われている
が、従来までの有機光導電材料を正孔輸送材料として用
いた電子写真感光体は、帯電性、感度および残留電位な
どの電子写真特性が、必ずしも満足されているものとは
言えないのが現状であり、優れた電荷輸送能力を有し、
耐久性のある正孔輸送材料の開発が望まれていた。Further, as a technique utilizing the hole transport material, there is an electrophotographic photoreceptor. The electrophotographic method is
It is one of the image forming methods invented by Carlson.
In this method, after the photoconductor is charged by corona discharge, it is exposed to a light image to obtain an electrostatic latent image on the photoconductor, toner is attached to the electrostatic latent image for development, and the obtained toner image is printed on a paper. Consists of transferring to. The basic characteristics required for a photoconductor in such an electrophotographic system are that an appropriate potential is maintained in a dark place, that there is little discharge of electric charge in a dark place, and that light is rapidly discharged by light irradiation. There are things to do. Conventional electrophotographic photoreceptors have used inorganic photoconductors such as selenium, selenium alloys, zinc oxide, cadmium sulfide and tellurium. These inorganic photoconductors have advantages such as high durability and a large number of printable sheets, but problems such as high manufacturing cost, poor processability, and toxicity have been pointed out. . Although organic photoconductors have been developed to overcome these drawbacks, electrophotographic photoconductors using a conventional organic photoconductive material as a hole transport material have not been improved in charging property, sensitivity and residual potential. At present, the electrophotographic properties are not always satisfactory, and they have excellent charge transporting ability,
It has been desired to develop a durable hole transport material.
【０００７】[0007]
【発明が解決しようとする課題】本発明の目的は、優れ
た正孔輸送能力を有し、耐久性のある正孔輸送材料とし
て有用なトリフェニルアミン重合体、その製造方法およ
びその用途を提供することにある。DISCLOSURE OF THE INVENTION An object of the present invention is to provide a triphenylamine polymer having an excellent hole-transporting ability and useful as a durable hole-transporting material, a method for producing the same, and its use. To do.
【０００８】[0008]
【課題を解決するための手段】即ち、本発明は、下記一
般式［１］で示されるトリフェニルアミン重合体であ
る。一般式［１］Means for Solving the Problems That is, the present invention is a triphenylamine polymer represented by the following general formula [1]. General formula [1]
【化３】 ［式中、Ｒ1〜Ｒ3は、それぞれ独立に、水素原子、置換
もしくは未置換のアルキル基、置換もしくは未置換のア
ルコキシ基、置換もしくは未置換のジアルキルアミノ基
である。ｎは１以上５０００以下の整数である。］Embedded image [Wherein, R 1 to R 3 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted dialkylamino group. n is an integer of 1 or more and 5000 or less. ]
【０００９】更に、本発明は、シクロヘキサノンと下記
一般式［２］で示されるトリフェニルアミン化合物とを
反応させることを特徴とするトリフェニルアミン重合体
の製造方法である。一般式［２］Furthermore, the present invention is a method for producing a triphenylamine polymer, which comprises reacting cyclohexanone with a triphenylamine compound represented by the following general formula [2]. General formula [2]
【化４】 ［式中、Ｒ1〜Ｒ3は、それぞれ独立に、水素原子、置換
もしくは未置換のアルキル基、置換もしくは未置換のア
ルコキシ基、置換もしくは未置換のジアルキルアミノ基
である。］[Chemical 4] [Wherein, R 1 to R 3 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted dialkylamino group. ]
【００１０】更に、本発明は、上記トリフェニルアミン
重合体からなる正孔輸送材料である。Furthermore, the present invention is a hole transport material comprising the above-mentioned triphenylamine polymer.
【００１１】更に、本発明は、一対の電極間に発光層ま
たは発光層を含む複数層の有機化合物薄膜を備えた有機
エレクトロルミネッセンス素子において、少なくとも一
層が該正孔輸送材料を含有する有機エレクトロルミネッ
センス素子である。Further, the present invention provides an organic electroluminescence device comprising a light emitting layer or a plurality of organic compound thin films including a light emitting layer between a pair of electrodes, at least one of which contains the hole transporting material. It is an element.
【００１２】更に、本発明は、導電性支持体上に、電荷
発生材料および正孔輸送材料を使用してなる電子写真感
光体において、正孔輸送材料が、該正孔輸送材料である
ことを特徴とする電子写真感光体である。Furthermore, the present invention provides an electrophotographic photosensitive member comprising a charge generating material and a hole transporting material on a conductive support, wherein the hole transporting material is the hole transporting material. It is a characteristic electrophotographic photoreceptor.
【００１３】[0013]
【発明の実施の形態】本発明における一般式［１］で示
される化合物の、Ｒ1〜Ｒ3は、それぞれ独立に、水素原
子、置換もしくは未置換のアルキル基、置換もしくは未
置換のアルコキシ基、置換もしくは未置換のジアルキル
アミノ基である。Ｒ1〜Ｒ3の具体例としては、例えば置
換もしくは未置換のアルキル基として、メチル基、エチ
ル基、プロピル基、ブチル基、ｓｅｃ−ブチル基、ｔｅ
ｒｔ−ブチル基、ペンチル基、ヘキシル基、ヘプチル
基、オクチル基、ステアリル基、トリクロロメチル基等
がある。置換もしくは未置換のアルコキシ基としては、
メトキシ基、エトキシ基、プロポキシ基、ｎ−ブトキシ
基、ｓｅｃ−ブトキシ基、ｔｅｒｔ−ブトキシ基、ペン
チルオキシ基、ヘキシルオキシ基、ステアリルオキシ
基、トリフロロメトキシ基等がある。置換もしくは未置
換のジアルキルアミノ基としては、ジメチルアミノ基、
ジエチルアミノ基、ジプロピルアミノ基、ジブチルアミ
ノ基等がある。BEST MODE FOR CARRYING OUT THE INVENTION In the compound represented by the general formula [1] in the present invention, R 1 to R 3 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group. , A substituted or unsubstituted dialkylamino group. Specific examples of R 1 to R 3 include, for example, a substituted or unsubstituted alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a sec-butyl group, and te.
There are rt-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, trichloromethyl group and the like. As the substituted or unsubstituted alkoxy group,
There are methoxy group, ethoxy group, propoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, stearyloxy group, trifluoromethoxy group and the like. As the substituted or unsubstituted dialkylamino group, a dimethylamino group,
There are a diethylamino group, a dipropylamino group, a dibutylamino group and the like.
【００１４】本発明において、一般式［１］で示される
化合物は、新規物質であり、例えば以下の方法により製
造することができる。酢酸溶媒中、シクロヘキサノン
に、２〜４倍モルの前記一般式［２］で示される置換基
を有するトリフェニルアミン化合物を、メタンスルホン
酸等の酸触媒と共に１００℃にて３０時間脱水反応させ
ることにより、一般式［１］で示されるトリフェニルア
ミン重合体を製造することができる。また、本発明で用
いられる酸触媒としては、メタンスルホン酸の代わり
に、トリフルオロ酢酸、ｐ−トルエンスルホン酸の様な
有機酸、または、硫酸、塩酸、ルイス酸等も可能であ
る。また、有機溶剤としては、酢酸の他に、１，４−ジ
オキサン、エーテル、石油エーテル等も可能である。こ
こで、反応時間を５０時間以上にすることにより、分子
量１万以上の化合物が多く合成され、逆に２０時間以下
であると、分子量２０００以下となる。In the present invention, the compound represented by the general formula [1] is a novel substance and can be produced, for example, by the following method. Cyclohexanone in an acetic acid solvent is dehydrated by a 2- to 4-fold molar amount of a triphenylamine compound having a substituent represented by the general formula [2] together with an acid catalyst such as methanesulfonic acid at 100 ° C. for 30 hours. Thus, the triphenylamine polymer represented by the general formula [1] can be produced. The acid catalyst used in the present invention may be an organic acid such as trifluoroacetic acid or p-toluenesulfonic acid, or sulfuric acid, hydrochloric acid, Lewis acid or the like, instead of methanesulfonic acid. In addition to acetic acid, 1,4-dioxane, ether, petroleum ether and the like can be used as the organic solvent. Here, by setting the reaction time to 50 hours or more, many compounds having a molecular weight of 10,000 or more are synthesized, and conversely, if the reaction time is 20 hours or less, the molecular weight becomes 2000 or less.
【００１５】以下に、本発明の化合物の代表例を、表
１，表２に具体的に例示するが、本発明は以下の代表例
に限定されるものではない。Representative examples of the compounds of the present invention are specifically shown in Tables 1 and 2 below, but the present invention is not limited to the following representative examples.
【００１６】[0016]
【表１】 [Table 1]
【００１７】 [0017]
【００１８】 [0018]
【００１９】 [0019]
【００２０】[0020]
【表２】 [Table 2]
【００２１】本発明の正孔輸送材料は、他の正孔もしく
は電子輸送性化合物と混合して使用してもさしつかえな
い。本発明の化合物は正孔輸送性に優れているので、正
孔輸送性材料として極めて有効に使用することができ
る。The hole-transporting material of the present invention may be used as a mixture with another hole- or electron-transporting compound. Since the compound of the present invention has an excellent hole transporting property, it can be used very effectively as a hole transporting material.
【００２２】また、請求項２記載の製造方法は、シクロ
ヘキサノンと前記一般式［２］で示されるトリフェニル
アミン誘導体との脱水反応を利用する方法であり、工業
的にも極めて有用な製造方法である。The production method according to claim 2 is a method utilizing a dehydration reaction between cyclohexanone and the triphenylamine derivative represented by the general formula [2], which is an industrially extremely useful production method. is there.
【００２３】まず、一般式［１］で示される化合物を有
機ＥＬ素子の正孔輸送材料として用いる場合について説
明する。図１〜３に、本発明で使用される有機ＥＬ素子
の模式図の一例を示した。図中、一般的に電極Ａである
２は陽極であり、電極Ｂである６は陰極である。また、
（電極Ａ／発光層／電子注入層／電極Ｂ）の層構成で積
層した有機ＥＬ素子もあり、一般式［１］の化合物は、
どの素子構成においても好適に使用することが出来る。
一般式［１］の化合物は、大きな正孔輸送能力をもって
いるので、正孔注入層３もしくは発光層４のいずれの層
においても、正孔輸送材料として使用できる。First, the case where the compound represented by the general formula [1] is used as a hole transport material of an organic EL device will be described. 1 to 3 show examples of schematic views of the organic EL device used in the present invention. In the figure, generally, the electrode A 2 is an anode, and the electrode B 6 is a cathode. Also,
There is also an organic EL device laminated in a layer structure of (electrode A / light emitting layer / electron injection layer / electrode B), and the compound of the general formula [1] is
It can be suitably used in any element configuration.
Since the compound of the general formula [1] has a large hole transporting ability, it can be used as a hole transporting material in either the hole injection layer 3 or the light emitting layer 4.
【００２４】図１の発光層４には、必要があれば、本発
明の一般式［１］の化合物に加えて、発光物質、発光補
助材料、キャリア輸送を行う正孔輸送材料や電子輸送材
料を使用することもできる。図２の構造は、発光層４と
正孔注入層３を分離している。この構造により、正孔注
入層３から発光層４への正孔注入効率が向上して、発光
輝度や発光効率を増加させることができる。この場合、
発光効率のためには、発光層に使用される発光物質自身
が電子輸送性であること、または発光層中に電子輸送輸
送材料を添加して発光層を電子輸送性にすることが望ま
しい。In the light emitting layer 4 of FIG. 1, if necessary, in addition to the compound of the general formula [1] of the present invention, a light emitting substance, a light emission auxiliary material, a hole transporting material for carrying carriers, and an electron transporting material. Can also be used. In the structure of FIG. 2, the light emitting layer 4 and the hole injection layer 3 are separated. With this structure, the hole injection efficiency from the hole injection layer 3 to the light emitting layer 4 is improved, and the light emission brightness and the light emission efficiency can be increased. in this case,
For light emission efficiency, it is desirable that the light emitting material used in the light emitting layer itself has an electron transporting property or that the light emitting layer has an electron transporting property by adding an electron transporting material.
【００２５】図３の構造は、正孔注入層３に加えて電子
注入層５を有し、発光層４での正孔と電子の再結合の効
率を向上させている。このように、有機ＥＬ素子を多層
構造にすることにより、クエンチングによる輝度や寿命
の低下を防ぐことができる。図２および図３の素子にお
いても、必要があれば、発光物質、発光補助材料、キャ
リア輸送を行う正孔輸送材料や電子輸送材料を組み合わ
せて使用することが出来る。また、正孔注入層、発光
層、電子注入層は、それぞれ二層以上の層構成により形
成されても良い。The structure of FIG. 3 has an electron injection layer 5 in addition to the hole injection layer 3 to improve the efficiency of recombination of holes and electrons in the light emitting layer 4. As described above, by forming the organic EL element into a multi-layer structure, it is possible to prevent a decrease in brightness and life due to quenching. Also in the elements of FIGS. 2 and 3, if necessary, a light emitting substance, a light emission auxiliary material, a hole transporting material for carrier transport, and an electron transporting material can be used in combination. Further, each of the hole injection layer, the light emitting layer, and the electron injection layer may be formed in a layer structure of two or more layers.
【００２６】有機ＥＬ素子の陽極に使用される導電性物
質としては、４ｅＶより大きな仕事関数を持つものが好
適であり、炭素、アルミニウム、バナジウム、鉄、コバ
ルト、ニッケル、タングステン、銀、金、白金、パラジ
ウム等およびそれらの合金、ＩＴＯ基板、ＮＥＳＡ基板
と称される酸化スズ、酸化インジウム等の酸化金属、さ
らにはポリチオフェンやポリピロール等の有機導電性樹
脂が用いられる。陰極に使用される導電性物質として
は、４ｅＶより小さな仕事関数を持つものが好適であ
り、マグネシウム、カルシウム、錫、鉛、チタニウム、
イットリウム、リチウム、ルテニウム、マンガン等およ
びそれらの合金が用いられるが、これらに限定されるも
のではない。陽極および陰極は、必要があれば二層以上
の層構成により形成されていても良い。As the conductive material used for the anode of the organic EL device, one having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum. , Palladium and their alloys, ITO substrates, metal oxides such as tin oxide and indium oxide called NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used. As the conductive material used for the cathode, one having a work function smaller than 4 eV is suitable, and magnesium, calcium, tin, lead, titanium,
Yttrium, lithium, ruthenium, manganese and the like and alloys thereof are used, but not limited to these. The anode and the cathode may be formed in a layered structure of two or more layers if necessary.
【００２７】有機ＥＬ素子では、効率良く発光させるた
めに、２で示される電極Ａまたは６で示される電極Ｂの
うち、少なくとも一方は素子の発光波長領域において充
分透明にすることが望ましい。また、基板１も透明であ
ることが望ましい。透明電極は、上記した導電性物質を
使用して、蒸着やスパッタリング等の方法で所定の透光
性が確保するように設定する。発光面の電極は、光透過
率を１０％以上にすることが望ましい。In the organic EL device, at least one of the electrode A shown by 2 and the electrode B shown by 6 is preferably sufficiently transparent in the emission wavelength region of the device in order to emit light efficiently. Further, it is desirable that the substrate 1 is also transparent. The transparent electrode is made of the above-mentioned conductive material and is set by a method such as vapor deposition or sputtering so as to ensure a predetermined translucency. The electrode on the light emitting surface preferably has a light transmittance of 10% or more.
【００２８】基板１は、機械的、熱的強度を有し、透明
なものであれば限定されるものではないが、例示する
と、ガラス基板、ポリエチレン板、ポリエーテルサルフ
ォン板、ポリプロピレン板等の透明樹脂があげられる。The substrate 1 is not limited as long as it has mechanical and thermal strength and is transparent, but examples thereof include a glass substrate, a polyethylene plate, a polyether sulfone plate, and a polypropylene plate. Examples include transparent resins.
【００２９】本発明に係わる有機ＥＬ素子の各層の形成
は、真空蒸着、スパッタリング等の乾式成膜法やスピン
コーティング、ディッピング等の湿式成膜法のいずれの
方法を適用することができる。膜厚は特に限定されるも
のではないが、各層は適切な膜厚に設定する必要があ
る。膜厚が厚すぎると、一定の光出力を得るために大き
な印加電圧が必要になり効率が悪くなる。膜厚が薄すぎ
るとピンホール等が発生して、電界を印加しても充分な
発光輝度が得られない。通常の膜厚は５ｎｍから１０μ
ｍの範囲が好適であるが、１０ｎｍから０．２μｍの範
囲がさらに好ましい。For formation of each layer of the organic EL device according to the present invention, any of dry film forming methods such as vacuum deposition and sputtering, and wet film forming methods such as spin coating and dipping can be applied. The film thickness is not particularly limited, but each layer needs to be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like will occur, and even if an electric field is applied, sufficient emission brightness cannot be obtained. Normal film thickness is 5nm to 10μ
The range of m is preferred, but the range of 10 nm to 0.2 μm is more preferred.
【００３０】湿式成膜法の場合、各層を形成する材料
を、クロロフォルム、テトラヒドロフラン、ジオキサン
等の適切な溶媒に溶解または分散して薄膜を形成する
が、その溶媒はいずれであっても良い。また、いずれの
薄膜においても、成膜性向上、膜のピンホール防止等の
ため適切な樹脂や添加剤を使用しても良い。このような
樹脂としては、ポリスチレン、ポリカーボネート、ポリ
アリレート、ポリエステル、ポリアミド、ポリウレタ
ン、ポリスルフォン、ポリメチルメタクリレート、ポリ
メチルアクリレート、セルロース等の絶縁性樹脂、ポリ
−Ｎ−ビニルカルバゾール、ポリシラン等の光導電性樹
脂、ポリチオフェン、ポリピロール等の導電性樹脂を挙
げることができる。In the case of the wet film forming method, the material forming each layer is dissolved or dispersed in an appropriate solvent such as chloroform, tetrahydrofuran, dioxane to form a thin film, and any solvent may be used. Further, in any of the thin films, an appropriate resin or additive may be used in order to improve the film forming property and prevent pinholes in the film. Examples of such resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethylmethacrylate, polymethylacrylate and cellulose, and photoconductive materials such as poly-N-vinylcarbazole and polysilane. Examples of the conductive resin include conductive resins such as polythiophene and polypyrrole.
【００３１】本有機ＥＬ素子は、発光層、正孔注入層、
電子注入層において、必要があれば、一般式［１］の化
合物に加えて、公知の発光物質、発光補助材料、正孔輸
送材料、電子輸送材料を使用することもできる。This organic EL device comprises a light emitting layer, a hole injection layer,
In the electron injection layer, if necessary, in addition to the compound of the general formula [1], a known light emitting substance, light emission auxiliary material, hole transporting material, or electron transporting material can be used.
【００３２】公知の発光物質または発光物質の補助材料
としては、アントラセン、ナフタレン、フェナントレ
ン、ピレン、テトラセン、コロネン、クリセン、フルオ
レセイン、ペリレン、フタロペリレン、ナフタロペリレ
ン、ペリノン、フタロペリノン、ナフタロペリノン、ジ
フェニルブタジエン、テトラフェニルブタジエン、クマ
リン、オキサジアゾール、アルダジン、ビスベンゾキサ
ゾリン、ビススチリル、ピラジン、シクロペンタジエ
ン、オキシン、アミノキノリン、イミン、ジフェニルエ
チレン、ビニルアントラセン、ジアミノカルバゾール、
ピラン、チオピラン、ポリメチン、メロシアニン、イミ
ダゾールキレート化オキシノイド化合物、キナクリド
ン、ルブレン等およびそれらの誘導体があるが、これら
に限定されるものではない。Known luminescent substances or auxiliary substances for luminescent substances include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene. , Coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, oxine, aminoquinoline, imine, diphenylethylene, vinylanthracene, diaminocarbazole,
Examples include, but are not limited to, pyran, thiopyran, polymethine, merocyanine, imidazole chelated oxinoid compounds, quinacridone, rubrene, and the like and their derivatives.
【００３３】一般式［１］の正孔輸送材料と併せて使用
できる正孔輸送材料としては、正孔を輸送する能力を持
ち、発光層または発光物質に対して優れた正孔注入効果
を有し、発光層で生成した励起子の電子注入層または電
子輸送材料への移動を防止し、かつ薄膜形成能の優れた
化合物が挙げられる。具体的には、フタロシアニン系化
合物、ナフタロシアニン系化合物、ポルフィリン系化合
物、オキサジアゾール、トリアゾール、イミダゾール、
イミダゾロン、イミダゾールチオン、ピラゾリン、ピラ
ゾロン、テトラヒドロイミダゾール、オキサゾール、オ
キサジアゾール、ヒドラゾン、アシルヒドラゾン、ポリ
アリールアルカン、スチルベン、ブタジエン、ベンジジ
ン型トリフェニルアミン、スチリルアミン型トリフェニ
ルアミン、ジアミン型トリフェニルアミン等と、それら
の誘導体、およびポリビニルカルバゾール、ポリシラ
ン、導電性高分子等の高分子材料等があるが、これらに
限定されるものではない。The hole transporting material that can be used in combination with the hole transporting material of the general formula [1] has the ability to transport holes and has an excellent hole injecting effect on the light emitting layer or the light emitting material. However, compounds that can prevent excitons generated in the light emitting layer from moving to the electron injection layer or the electron transport material and have excellent thin film forming ability can be given. Specifically, phthalocyanine compounds, naphthalocyanine compounds, porphyrin compounds, oxadiazoles, triazoles, imidazoles,
Imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene, benzidine type triphenylamine, styrylamine type triphenylamine, diamine type triphenylamine, etc. Examples thereof include, but are not limited to, derivatives thereof, and polymeric materials such as polyvinylcarbazole, polysilane, and conductive polymers.
【００３４】電子輸送材料としては、電子を輸送する能
力を持ち、発光層または発光物質に対して優れた電子注
入効果を有し、発光層で生成した励起子の正孔注入層ま
たは正孔輸送材料への移動を防止し、かつ薄膜形成能の
優れた化合物が挙げられる。例えば、フルオレノン、ア
ントラキノジメタン、ジフェノキノン、チオピランジオ
キシド、オキサジアゾール、ペリレンテトラカルボン
酸、フレオレニリデンメタン、アントラキノジメタン、
アントロン等とそれらの誘導体があるが、これらに限定
されるものではない。また、正孔輸送材料に電子受容物
質を、電子輸送材料に電子供与性物質を添加することに
より増感させることもできる。The electron-transporting material has the ability to transport electrons, has an excellent electron-injecting effect on the light-emitting layer or the light-emitting substance, and has a hole-injecting layer or hole-transporting layer for excitons generated in the light-emitting layer. Examples thereof include compounds that prevent transfer to the material and have excellent thin film forming ability. For example, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxadiazole, perylene tetracarboxylic acid, fluorenylidene methane, anthraquinodimethane,
Examples include, but are not limited to, anthrone and derivatives thereof. It is also possible to sensitize by adding an electron accepting substance to the hole transporting material and adding an electron donating substance to the electron transporting material.
【００３５】図１，２および３に示される有機ＥＬ素子
において、本発明の一般式［１］の化合物は、いずれの
層に使用することができ、一般式［１］の化合物の他
に、発光物質、発光補助材料、正孔輸送材料および電子
輸送材料の少なくとも１種が同一層に含有されてもよ
い。また、本発明により得られた有機ＥＬ素子の、温
度、湿度、雰囲気等に対する安定性の向上のために、素
子の表面に保護層を設けたり、シリコンオイル等を封入
して素子全体を保護することも可能である。以上のよう
に、本発明では有機ＥＬ素子に一般式［１］の化合物を
用いたため、発光効率と発光輝度を高くできた。また、
この素子は熱や電流に対して非常に安定であり、さらに
は低い駆動電圧で実用的に使用可能の発光輝度が得られ
るため、従来まで大きな問題であった劣化も大幅に低下
させることができた。In the organic EL devices shown in FIGS. 1, 2 and 3, the compound of the general formula [1] of the present invention can be used in any layer, and in addition to the compound of the general formula [1], At least one of a light emitting substance, a light emission assisting material, a hole transporting material and an electron transporting material may be contained in the same layer. Further, in order to improve the stability of the organic EL element obtained by the present invention against temperature, humidity, atmosphere, etc., a protective layer is provided on the surface of the element or silicon oil or the like is enclosed to protect the entire element. It is also possible. As described above, in the present invention, since the compound of the general formula [1] is used for the organic EL device, the luminous efficiency and the luminous brightness can be increased. Also,
This device is extremely stable against heat and current, and because it can obtain practically usable light emission brightness at a low driving voltage, it is possible to greatly reduce deterioration, which was a big problem until now. It was
【００３６】本発明の有機ＥＬ素子は、壁掛けテレビ等
のフラットパネルディスプレイや、平面発光体として、
複写機やプリンター等の光源、液晶ディスプレイや計器
類等の光源、表示板、標識灯等へ応用が考えられ、その
工業的価値は非常に大きい。The organic EL device of the present invention is used as a flat panel display such as a wall-mounted TV or a flat light-emitting body.
It can be applied to light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, marker lights, etc., and its industrial value is very large.
【００３７】次に、本発明の一般式［１］で示される化
合物を電子写真感光体として用いる場合について説明す
る。本発明の一般式［１］で示される化合物は、電子写
真感光体の何れの層においても使用できるが、高い正孔
輸送特性を有することから正孔輸送材料として使用する
ことが望ましい。該化合物は正孔輸送物質として作用
し、光を吸収することにより発生した電荷を極めて効率
よく輸送でき、高速応答性に優れた感光体を得ることが
できる。また、該化合物は、耐オゾン性、光安定性に優
れているので、耐久性に優れた感光体を得ることができ
る。Next, the case where the compound represented by the general formula [1] of the present invention is used as an electrophotographic photoreceptor will be described. The compound represented by the general formula [1] of the present invention can be used in any layer of an electrophotographic photoreceptor, but it is preferably used as a hole transport material because it has high hole transport properties. The compound acts as a hole-transporting substance, can transport charges generated by absorbing light extremely efficiently, and can provide a photoreceptor having excellent high-speed response. Further, since the compound is excellent in ozone resistance and light stability, a photoreceptor having excellent durability can be obtained.
【００３８】電子写真感光体は、導電性基板上に電荷発
生材料と、必要があれば電荷輸送材料を結着樹脂に分散
させてなる感光層を設けた単層型感光体、導電性基板上
に下引き層、電荷発生層、正孔輸送層の順に積層した、
もしくは導電性基板または下引き層上に正孔輸送層、電
荷発生層の順に積層した積層型感光体等がある。ここ
で、下引き層は必要がなければ使用しなくても良い。上
記感光体は、必要があれば活性ガスからの表面保護およ
びトナーによるフィルミング防止等の意味でオーバーコ
ート層を設けることも出来る。The electrophotographic photosensitive member is a single-layer type photosensitive member in which a charge generating material and, if necessary, a photosensitive layer in which a charge transporting material is dispersed in a binder resin are provided on a conductive substrate. An undercoat layer, a charge generation layer, and a hole transport layer in this order,
Alternatively, there is a laminated type photoreceptor in which a hole transport layer and a charge generation layer are laminated in this order on a conductive substrate or an undercoat layer. Here, the undercoat layer may not be used if not necessary. If necessary, the photoreceptor may be provided with an overcoat layer for the purpose of protecting the surface from active gas and preventing filming by toner.
【００３９】電荷発生材料としては、ビスアゾ、キナク
リドン、ジケトピロロピロール、インジゴ、ペリレン、
ペリノン、多環キノン、スクアリリウム塩、アズレニウ
ム塩、フタロシアニン、ナフタロシアニン等の有機化合
物、もしくは、セレン、セレン−テルル合金、硫化カド
ミウム、酸化亜鉛、アモルファスシリコン等の無機物質
が挙げられる。As the charge generating material, bisazo, quinacridone, diketopyrrolopyrrole, indigo, perylene,
Examples thereof include organic compounds such as perinone, polycyclic quinone, squarylium salt, azurenium salt, phthalocyanine, and naphthalocyanine, and inorganic substances such as selenium, selenium-tellurium alloy, cadmium sulfide, zinc oxide, and amorphous silicon.
【００４０】感光体の各層は蒸着もしくは分散塗工方式
により成膜することが出来る。分散塗工は、スピンコー
ター、アプリケーター、スプレーコーター、浸漬コータ
ー、ローラーコーター、カーテンコーターおよびビード
コーター等を用いて行い、乾燥は室温から２００℃、１
０分から６時間の範囲で静止または送風条件下で行う。
乾燥後の感光層の膜厚は単層型感光体の場合、５μｍか
ら５０μｍ、積層型感光体の場合、電荷発生層は０．０
１μｍから５μｍ、好ましくは０．１μｍから１μｍで
あり、正孔輸送層は５μｍから５０μｍ、好ましくは１
０μｍから２０μｍが適している。Each layer of the photoreceptor can be formed by vapor deposition or dispersion coating method. Dispersion coating is performed using a spin coater, an applicator, a spray coater, a dip coater, a roller coater, a curtain coater, a bead coater, etc., and drying is from room temperature to 200 ° C., 1
It is performed under static or blown conditions in the range of 0 minutes to 6 hours.
The film thickness of the photosensitive layer after drying is 5 μm to 50 μm in the case of a single-layer type photoconductor, and 0.0 in the case of a multilayer type photoconductor.
1 μm to 5 μm, preferably 0.1 μm to 1 μm, the hole transport layer is 5 μm to 50 μm, preferably 1
0 μm to 20 μm is suitable.
【００４１】単層型感光体の感光層、積層型感光体の電
荷発生層もしくは正孔輸送層を形成する際に使用する樹
脂は広範な絶縁性樹脂から選択出来る。また、ポリ−Ｎ
−ビニルカルバゾール、ポリビニルアントラセンやポリ
シラン類などの有機光導電性ポリマーから選択出来る。
好ましくは、ポリビニルブチラール、ポリアリレート、
ポリカーボネート、ポリエステル、フェノキシ、アクリ
ル、ポリアミド、ウレタン、エポキシ、シリコン、ポリ
スチレン、ポリ塩化ビニル、塩酢ビ共重合体、フェノー
ルおよびメラミン樹脂等の絶縁性樹脂を挙げることが出
来る。電荷発生層もしくは正孔輸送層を形成するために
使用される樹脂は、電荷発生材料もしくは正孔輸送材料
に対して、１００重量％以下が好ましいがこの限りでは
ない。樹脂は２種類以上組み合わせて使用しても良い。
また、必要があれば樹脂を使用しなくてもよい。また、
電荷発生層を蒸着、スパッタリング等の物理的成膜法に
より形成させることも出来る。蒸着、スパッタリング法
では、好ましくは１０-5Ｔｏｏｒ以下の真空雰囲気下で
成膜することが望ましい。また、窒素、アルゴン、ヘリ
ウム等の不活性ガス中で成膜することも可能である。The resin used for forming the photosensitive layer of the single-layer type photoreceptor, the charge generation layer or the hole transport layer of the laminated type photoreceptor can be selected from a wide range of insulating resins. Also, poly-N
-Selectable from organic photoconductive polymers such as vinylcarbazole, polyvinylanthracene and polysilanes.
Preferably, polyvinyl butyral, polyarylate,
Insulating resins such as polycarbonate, polyester, phenoxy, acrylic, polyamide, urethane, epoxy, silicon, polystyrene, polyvinyl chloride, vinyl chloride / vinyl acetate copolymer, phenol and melamine resin can be mentioned. The resin used for forming the charge generation layer or the hole transport layer is preferably 100% by weight or less with respect to the charge generation material or the hole transport material, but is not limited thereto. You may use resin in combination of 2 or more types.
Further, if necessary, the resin may not be used. Also,
The charge generation layer can also be formed by a physical film forming method such as vapor deposition or sputtering. In the vapor deposition or sputtering method, it is desirable to form the film in a vacuum atmosphere of preferably 10 −5 Toor or less. It is also possible to form a film in an inert gas such as nitrogen, argon, or helium.
【００４２】電子写真感光体の各層を形成する際に使用
する溶剤は、下引き層や他の感光層に影響を与えないも
のから選択することが好ましい。具体的には、ベンゼ
ン、キシレン等の芳香族炭化水素、アセトン、メチルエ
チルケトン、シクロヘキサノン等のケトン類、メタノー
ル、エタノール等のアルコール類、酢酸エチル、メチル
セロソルブ等のエステル類、四塩化炭素、クロロホル
ム、ジクロロメタン、ジクロロエタン、トリクロロエチ
レン等の脂肪族ハロゲン化炭化水素類、クロルベンゼ
ン、ジクロルベンゼン等の芳香族ハロゲン化炭化水素
類、テトラヒドロフラン、ジオキサン等のエーテル類等
が用いられるがこれらに限られるものではない。The solvent used when forming each layer of the electrophotographic photosensitive member is preferably selected from those which do not affect the undercoat layer and other photosensitive layers. Specifically, aromatic hydrocarbons such as benzene and xylene, ketones such as acetone, methyl ethyl ketone and cyclohexanone, alcohols such as methanol and ethanol, esters such as ethyl acetate and methyl cellosolve, carbon tetrachloride, chloroform and dichloromethane. However, aliphatic halogenated hydrocarbons such as dichloroethane and trichloroethylene, aromatic halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, and ethers such as tetrahydrofuran and dioxane are used, but not limited thereto.
【００４３】正孔輸送層は正孔輸送材料のみ、もしくは
正孔輸送材料を樹脂に溶解させた塗液を塗布することに
より形成される。本感光体に使用される正孔輸送材料
は、一般式［１］の化合物に加えて他の正孔輸送材料を
組み合わせて使用することもできる。一般式［１］の化
合物は、他の樹脂との相溶性が良く、結晶が析出しにく
いので、感度、耐久性の向上のために有利である。The hole-transporting layer is formed by applying a hole-transporting material alone or a coating solution prepared by dissolving the hole-transporting material in a resin. The hole transport material used in the present photoreceptor may be used in combination with other hole transport materials in addition to the compound of the general formula [1]. The compound of the general formula [1] has good compatibility with other resins and is less prone to crystal precipitation, and is therefore advantageous for improving sensitivity and durability.
【００４４】電子写真特性、画像特性等の向上のため
に、必要があれば基板と有機層の間に下引き層を設ける
ことができ、下引き層としてはポリアミド類、カゼイ
ン、ポリビニルアルコール、ゼラチン、ポリビニルブチ
ラール等の樹脂類、酸化アルミニウム等の金属酸化物な
どが用いられる。In order to improve electrophotographic characteristics, image characteristics, etc., an undercoat layer can be provided between the substrate and the organic layer, if necessary. As the undercoat layer, polyamides, casein, polyvinyl alcohol, gelatin are used. Resins such as polyvinyl butyral and metal oxides such as aluminum oxide are used.
【００４５】本発明の材料は、有機ＥＬ素子もしくは電
子写真感光体等の正孔輸送材料としのみでなく、光電変
換素子、太陽電池、イメージセンサー等の分野において
も好適に使用できる。The material of the present invention can be suitably used not only as a hole transporting material for an organic EL device or an electrophotographic photoreceptor but also in the fields of photoelectric conversion devices, solar cells, image sensors and the like.
【００４６】[0046]
【実施例】以下、本発明を実施例に基づきさらに詳細に
説明する。化合物（１）の合成方法 酢酸１５部中に、シクロヘキサノン１０部、トリフェニ
ルアミン１７部、およびメタンスルホン酸０．５部を入
れ、１００℃にて１０時間加熱撹拌した。その後、５０
０部の水で希釈し、希水酸化ナトリウム水溶液で中和し
た。この後、酢酸エチルで抽出を行い、濃縮し、シリカ
ゲルを用いたカラムクロマトグラフィーにより精製を行
ない白色の蛍光を有する粉末８部を得た。ＧＰＣによる
分子量分析の結果、化合物（１）であることを確認し
た。平均分子量は、ＧＰＣ（ＧｅｌＰｅｒｍｅａｔｉｏ
ｎ Ｃｈｒｏｍａｔｏｇｒａｐｈｙ）よりポリスチレン
関算の重量平均分子量の値として求めた。以下に生成物
の元素分析結果を示す。 元素分析結果 Ｃ66Ｈ61Ｎ3として 計算値（％）：Ｃ：８８．５８ Ｈ：６．７６
Ｎ：４．６６ 実測値（％）：Ｃ：８８．２９ Ｈ：６．６３
Ｎ：５．０８ この化合物の赤外吸収スペクトル（ＫＢｒ錠剤法）を図
１に示す。The present invention will be described in more detail based on the following examples. Method for synthesizing compound (1) In 15 parts of acetic acid, 10 parts of cyclohexanone, 17 parts of triphenylamine, and 0.5 parts of methanesulfonic acid were placed, and heated and stirred at 100 ° C. for 10 hours. Then 50
It was diluted with 0 part of water and neutralized with dilute aqueous sodium hydroxide solution. After that, extraction was performed with ethyl acetate, the mixture was concentrated, and purified by column chromatography using silica gel to obtain 8 parts of a powder having white fluorescence. As a result of molecular weight analysis by GPC, it was confirmed to be compound (1). The average molecular weight is GPC (GelPermeatio
n Chromatography) as a value of the weight average molecular weight in terms of polystyrene. The results of elemental analysis of the product are shown below. Elemental analysis result Calculated value (%) as C 66 H 61 N 3 : C: 88.58 H: 6.76
N: 4.66 Found (%): C: 88.29 H: 6.63
N: 5.08 The infrared absorption spectrum (KBr tablet method) of this compound is shown in FIG.
【００４７】化合物（２）の合成方法 酢酸３０部中に、シクロヘキサノン１０部、４−メチル
トリフェニルアミン２８部、およびメタンスルホン酸１
部を入れ、１０５℃にて３０時間加熱撹拌した。その
後、５００部の水で希釈し、希水酸化ナトリウム水溶液
で中和した。この後、酢酸エチルで抽出を行い、濃縮
し、シリカゲルを用いたカラムクロマトグラフィーによ
り精製して黄色の蛍光を有する粉末１３部を得た。ＧＰ
Ｃによる分子量分析の結果、化合物（２）であることを
確認した。以下に生成物の元素分析結果を示す。 元素分析結果 Ｃ144Ｈ142Ｎ6として 計算値（％）：Ｃ：８８．４３ Ｈ：７．２７
Ｎ：４．３０ 実測値（％）：Ｃ：８８．５８ Ｈ：７．１８
Ｎ：４．２４ この化合物の赤外吸収スペクトル（ＫＢｒ錠剤法）を図
２に示す。 Method for synthesizing compound (2) In 30 parts of acetic acid, 10 parts of cyclohexanone, 28 parts of 4-methyltriphenylamine, and 1 part of methanesulfonic acid.
A part was put thereinto, and the mixture was heated and stirred at 105 ° C. for 30 hours. Thereafter, the mixture was diluted with 500 parts of water and neutralized with a dilute aqueous sodium hydroxide solution. After that, extraction was performed with ethyl acetate, concentration, and purification by column chromatography using silica gel to obtain 13 parts of a powder having yellow fluorescence. GP
As a result of molecular weight analysis by C, it was confirmed to be the compound (2). The results of elemental analysis of the product are shown below. Elemental analysis result Calculated value (%) as C 144 H 142 N 6 : C: 88.43 H: 7.27
N: 4.30 Found (%): C: 88.58 H: 7.18
N: 4.24 The infrared absorption spectrum (KBr tablet method) of this compound is shown in FIG.
【００４８】化合物（１３）の合成方法 酢酸３０部中に、シクロヘキサノン８部、４−メトキシ
トリフェニルアミン２５部、およびメタンスルホン酸１
部を入れ、１０５℃にて３０時間加熱撹拌した。その
後、５００部の水で希釈し、希水酸化ナトリウム水溶液
で中和した。この後、酢酸エチルで抽出を行い、濃縮
し、シリカゲルを用いたカラムクロマトグラフィーによ
り精製して黄色の蛍光を有する粉末１３部を得た。ＧＰ
Ｃによる分子量分析の結果、化合物（１３）であること
を確認した。以下に生成物の元素分析結果を示す。 元素分析結果 Ｃ225Ｈ234Ｎ9Ｏ9として 計算値（％）：Ｃ：８４．２７ Ｈ：７．３０
Ｎ：３．９３ 実測値（％）：Ｃ：８４．６１ Ｈ：７．２１
Ｎ：３．８５ この化合物の赤外吸収スペクトル（ＫＢｒ錠剤法）を図
３に示す。 Method for synthesizing compound (13) In 30 parts of acetic acid, 8 parts of cyclohexanone, 25 parts of 4-methoxytriphenylamine, and 1 part of methanesulfonic acid are added.
A part was put thereinto, and the mixture was heated and stirred at 105 ° C. for 30 hours. Thereafter, the mixture was diluted with 500 parts of water and neutralized with a dilute aqueous sodium hydroxide solution. After that, extraction was performed with ethyl acetate, concentration, and purification by column chromatography using silica gel to obtain 13 parts of a powder having yellow fluorescence. GP
As a result of molecular weight analysis by C, it was confirmed to be the compound (13). The results of elemental analysis of the product are shown below. Elemental analysis result Calculated as C 225 H 234 N 9 O 9 (%): C: 84.27 H: 7.30
N: 3.93 actual value (%): C: 84.61 H: 7.21
N: 3.85 The infrared absorption spectrum (KBr tablet method) of this compound is shown in FIG.
【００４９】実施例１ 洗浄したＩＴＯ電極付きガラス板上に、化合物（１）、
トリス（８−ヒドロキシキノリン）アルミニウム錯体、
ポリカーボネート樹脂（ＰＣ−Ａ）を３：２：５の比率
でテトラヒドロフランに溶解させ、スピンコーティング
法により膜厚１００ｎｍの発光層を得た。その上に、マ
グネシウムと銀を１０：１で混合した合金で膜厚１５０
ｎｍの電極を形成して図４に示す有機ＥＬ素子を得た。
この素子は、直流電圧５Ｖで１８０ｃｄ／ｍ2の発光が
得られた。Example 1 On a washed glass plate with an ITO electrode, the compound (1),
Tris (8-hydroxyquinoline) aluminum complex,
Polycarbonate resin (PC-A) was dissolved in tetrahydrofuran at a ratio of 3: 2: 5, and a light emitting layer having a film thickness of 100 nm was obtained by a spin coating method. On top of that, an alloy of magnesium and silver mixed at a ratio of 10: 1 has a film thickness of 150.
nm electrode was formed to obtain the organic EL device shown in FIG.
With this device, light emission of 180 cd / m 2 was obtained at a DC voltage of 5V.
【００５０】実施例２ 洗浄したＩＴＯ電極付きガラス板上に、化合物（２）を
テトラヒドロフランに溶解させ、スピンコーティング法
により膜厚５０ｎｍの正孔注入層を得た。次いで、トリ
ス（８−ヒドロキシキノリン）アルミニウム錯体を真空
蒸着して膜厚３０ｎｍの発光層を作成し、その上に、マ
グネシウムと銀を１０：１で混合した合金で膜厚１００
ｎｍの電極を形成して図５に示す有機ＥＬ素子を得た。
正孔注入層および発光層は１０-6Ｔｏｒｒの真空中で、
基板温度室温の条件下で蒸着した。この素子は、直流電
圧５Ｖで約２３０ｃｄ／ｍ2の発光が得られた。Example 2 Compound (2) was dissolved in tetrahydrofuran on a washed glass plate with an ITO electrode, and a hole injection layer having a thickness of 50 nm was obtained by spin coating. Then, a tris (8-hydroxyquinoline) aluminum complex is vacuum-deposited to form a light-emitting layer having a thickness of 30 nm, and an alloy in which magnesium and silver are mixed at a ratio of 10: 1 has a thickness of 100 nm.
nm electrodes were formed to obtain the organic EL device shown in FIG.
The hole injection layer and the light emitting layer are in a vacuum of 10 −6 Torr,
Deposition was carried out under the condition that the substrate temperature was room temperature. This device emitted light of about 230 cd / m 2 at a DC voltage of 5V.
【００５１】実施例３ 洗浄したＩＴＯ電極付きガラス板上に、化合物（３）を
テトラヒドロフランに溶解させ、スピンコーティング法
により膜厚５０ｎｍの正孔注入層を得た。次いで、トリ
ス（８−ヒドロキシキノリン）アルミニウム錯体を真空
蒸着して膜厚３０ｎｍの発光層を作成し、その上に、マ
グネシウムと銀を１０：１で混合した合金で膜厚１００
ｎｍの電極を形成して図５に示す有機ＥＬ素子を得た。
発光層は１０-6Ｔｏｒｒの真空中で、基板温度室温の条
件下で蒸着した。この素子は、直流電圧５Ｖで約４００
ｃｄ／ｍ2の発光が得られた。Example 3 Compound (3) was dissolved in tetrahydrofuran on a washed glass plate with an ITO electrode, and a hole injection layer having a film thickness of 50 nm was obtained by spin coating. Then, a tris (8-hydroxyquinoline) aluminum complex is vacuum-deposited to form a light-emitting layer having a thickness of 30 nm, and an alloy in which magnesium and silver are mixed at a ratio of 10: 1 has a thickness of 100 nm.
nm electrodes were formed to obtain the organic EL device shown in FIG.
The light emitting layer was deposited in a vacuum of 10 -6 Torr at a substrate temperature of room temperature. This device has a DC voltage of 5 V
Light emission of cd / m 2 was obtained.
【００５２】実施例４ 正孔注入層に化合物（１３）を使用する以外は、実施例
３と同様の方法で有機ＥＬ素子を作製した。この素子
は、直流電圧５Ｖで約５１０ｃｄ／ｍ2の発光が得られ
た。Example 4 An organic EL device was prepared in the same manner as in Example 3 except that the compound (13) was used in the hole injection layer. With this device, light emission of about 510 cd / m 2 was obtained at a DC voltage of 5V.
【００５３】実施例５ 正孔注入層に化合物（１７）を使用する以外は、実施例
３と同様の方法で有機ＥＬ素子を作製した。この素子
は、直流電圧５Ｖで約４２０ｃｄ／ｍ2の発光が得られ
た。Example 5 An organic EL device was prepared in the same manner as in Example 3 except that the compound (17) was used in the hole injection layer. The device emitted light of about 420 cd / m 2 at a DC voltage of 5V.
【００５４】実施例６ 正孔注入層に化合物（１９）を使用する以外は、実施例
３と同様の方法で有機ＥＬ素子を作製した。この素子
は、直流電圧５Ｖで約５００ｃｄ／ｍ2の発光が得られ
た。Example 6 An organic EL device was produced in the same manner as in Example 3 except that the compound (19) was used in the hole injection layer. The device emitted light of about 500 cd / m 2 at a DC voltage of 5 V.
【００５５】実施例７ 洗浄したＩＴＯ電極付きガラス板上に、化合物（５）を
真空蒸着して、膜厚２０ｎｍの正孔注入層を得た。さら
に、Ｎ，Ｎ'―ジフェニル―Ｎ，Ｎ'―（３―チルフェニ
ル）―１，１'―ビフェニル―４，４'―ジアミンを真空
蒸着して、厚３０ｎｍの正孔輸送層を得た。次いで、ト
リス（８−ヒドロキシキノリン）アルミニウム錯体を真
空蒸着して膜厚３０ｎｍの発光層を作成し、その上に、
マグネシウムと銀を１０：１で混合した合金で膜厚１０
０ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入
層および発光層は１０-6Ｔｏｒｒの真空中で、基板温度
室温の条件下で蒸着した。この素子は、直流電圧５Ｖで
約３１０ｃｄ／ｍ2の発光が得られた。Example 7 Compound (5) was vacuum-deposited on a washed glass plate with an ITO electrode to obtain a hole injection layer having a film thickness of 20 nm. Further, N, N′-diphenyl-N, N ′-(3-tylphenyl) -1,1′-biphenyl-4,4′-diamine was vacuum-deposited to obtain a hole transport layer having a thickness of 30 nm. Next, a tris (8-hydroxyquinoline) aluminum complex is vacuum-deposited to form a light emitting layer having a film thickness of 30 nm, and
An alloy of magnesium and silver mixed at a ratio of 10: 1 and a film thickness of 10
An electrode of 0 nm was formed to obtain an organic EL device. The hole injecting layer and the light emitting layer were vapor-deposited in a vacuum of 10 −6 Torr at a substrate temperature of room temperature. The device emitted light of about 310 cd / m 2 at a DC voltage of 5V.
【００５６】実施例８ 洗浄したＩＴＯ電極付きガラス板上に、Ｎ，Ｎ'―ジフ
ェニル―Ｎ，Ｎ'―（―メチルフェニル）―１，１'―ビ
フェニル―４，４'―ジアミンを真空蒸着し、膜厚５０
ｎｍの正孔注入層を得た。次いで、トリス（８−ヒドロ
キシキノリン）アルミニウム錯体と化合物（７）を３：
１の割合で真空蒸着して膜厚５０ｎｍの発光層を作成
し、その上に、マグネシウムと銀を１０：１で混合した
合金で膜厚１５０ｎｍの膜厚の電極を形成して図５に示
す有機ＥＬ素子を得た。正孔注入層および発光層は１０
-6Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着し
た。この素子は、直流電圧５Ｖで約３６０ｃｄ／ｍ2の
発光が得られた。Example 8 N, N'-diphenyl-N, N '-(-methylphenyl) -1,1'-biphenyl-4,4'-diamine was vacuum-deposited on a washed glass plate with an ITO electrode. And film thickness 50
A hole injection layer of nm was obtained. Then, tris (8-hydroxyquinoline) aluminum complex and compound (7) were mixed with 3:
FIG. 5 shows a light-emitting layer having a thickness of 50 nm formed by vacuum evaporation at a ratio of 1 and an electrode having a thickness of 150 nm is formed on the light-emitting layer having a thickness of 50: 1. An organic EL device was obtained. 10 for the hole injection layer and the light emitting layer
Deposition was carried out in a vacuum of -6 Torr at a substrate temperature of room temperature. This device emitted light of about 360 cd / m 2 at a DC voltage of 5V.
【００５７】実施例９ 洗浄したＩＴＯ電極付きガラス板上に、化合物（９）を
クロロホルムに溶解させ、スピンコーティング法により
膜厚５０ｎｍの正孔注入層を得た。次いで、真空蒸着法
によりトリス（８−ヒドロキシキノリン）アルミニウム
錯体の膜厚５０ｎｍの発光層を作成し、さらに真空蒸着
法により［２−（４−ｔｅｒｔ−ブチルフェニル）−５
−（ビフェニル）−１，３，４−オキサジアゾール］の
膜厚２０ｎｍの電子注入層を得た。その上に、マグネシ
ウムと銀を１０：１で混合した合金で膜厚１５０ｎｍの
電極を形成して図６に示す有機ＥＬ素子を得た。この素
子は、直流電圧５Ｖで約４９０ｃｄ／ｍ2の発光が得ら
れた。Example 9 Compound (9) was dissolved in chloroform on a washed glass plate with an ITO electrode, and a hole injection layer having a thickness of 50 nm was obtained by spin coating. Then, a 50-nm-thick light-emitting layer of a tris (8-hydroxyquinoline) aluminum complex was formed by a vacuum evaporation method, and then [2- (4-tert-butylphenyl) -5 was formed by a vacuum evaporation method.
An electron injection layer having a film thickness of 20 nm of-(biphenyl) -1,3,4-oxadiazole] was obtained. An electrode having a film thickness of 150 nm was formed on it with an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device shown in FIG. The device emitted light of about 490 cd / m 2 at a DC voltage of 5V.
【００５８】本実施例で示された全ての有機ＥＬ素子に
ついて、１ｍＡ／ｃｍ2で連続発光させたところ、１０
００時間以上安定な発光を観測することができた。本発
明の有機ＥＬ素子は発光効率、発光輝度の向上と長寿命
化を達成するものであり、併せて使用される発光物質、
発光補助材料、正孔輸送材料、電子輸送材料、増感剤、
樹脂、電極材料等および素子作製方法を限定するもので
はない。When all the organic EL devices shown in this example were made to emit light continuously at 1 mA / cm 2 , 10
Stable light emission could be observed for 00 hours or more. The organic EL device of the present invention achieves improvement in luminous efficiency, luminous brightness, and long life.
Luminescent auxiliary material, hole transport material, electron transport material, sensitizer,
The resin, the electrode material and the like and the method for manufacturing the element are not limited.
【００５９】実施例１０ ε型銅フタロシアニン４ｇ、化合物（４）２ｇ、ポリエ
ステル樹脂（バイロン２００：東洋防（株）製）１４ｇ
をテトラヒドロフラン８０ｇと共にボールミルで５時間
分散した。この分散液をアルミニウム基板上に塗工、乾
燥して、図７に示す膜厚２０μｍの単層型電子写真感光
体を作製した。Example 10 4 g of ε-type copper phthalocyanine, 2 g of compound (4), and 14 g of polyester resin (Vylon 200: manufactured by Toyo Prevention Co., Ltd.)
Was dispersed with 80 g of tetrahydrofuran in a ball mill for 5 hours. This dispersion was applied onto an aluminum substrate and dried to prepare a single-layer type electrophotographic photoreceptor having a film thickness of 20 μm shown in FIG.
【００６０】実施例１１ ジブロモアントアントロン６ｇ、化合物（６）２ｇ、ポ
リエステル樹脂（バイロン２００：東洋防（株）製）１
２ｇをテトラヒドロフラン８０ｇと共にボールミルで５
時間分散した。この分散液をアルミニウム基板上に塗
工、乾燥して、図７に示す膜厚２０μｍの単層型電子写
真感光体を作製した。Example 11 6 g of dibromoanthanthrone, 2 g of compound (6), polyester resin (Vylon 200: manufactured by Toyo Prevention Co., Ltd.) 1
5 g of 2 g together with 80 g of tetrahydrofuran in a ball mill
Time dispersed. This dispersion was applied onto an aluminum substrate and dried to prepare a single-layer type electrophotographic photoreceptor having a film thickness of 20 μm shown in FIG.
【００６１】実施例１２ τ型無金属フタロシアニン２ｇ、ポリビニルブチラール
樹脂（ＢＨ−３：積水化学（株）製）２ｇをテトラヒド
ロフラン９６ｇと共にボールミルで２時間分散した。こ
の分散液をアルミニウム基板上に塗工、乾燥して、膜厚
０．３μｍの電荷発生層を作製した。次に化合物（１
０）１０ｇ、ポリカーボネート樹脂（Ｌ−１２５０；帝
人化成（株）製）１０ｇをジクロロメタン８０ｇに溶解
した。この塗液を電荷発生層上に塗工、乾燥して、膜厚
２０μｍの正孔輸送層を形成し、図８に示す積層型電子
写真感光体を作製した。Example 12 2 g of τ type metal-free phthalocyanine and 2 g of polyvinyl butyral resin (BH-3: manufactured by Sekisui Chemical Co., Ltd.) were dispersed together with 96 g of tetrahydrofuran in a ball mill for 2 hours. This dispersion was applied onto an aluminum substrate and dried to form a charge generation layer having a film thickness of 0.3 μm. Next, the compound (1
0) 10 g and a polycarbonate resin (L-1250; manufactured by Teijin Chemicals Ltd.) 10 g were dissolved in 80 g of dichloromethane. This coating liquid was applied onto the charge generation layer and dried to form a hole transport layer having a film thickness of 20 μm, and the laminated electrophotographic photoreceptor shown in FIG. 8 was produced.
【００６２】実施例１３ 正孔輸送層に化合物（１６）を使用する以外は実施例１
２と同様の方法で積層型電子写真感光体を作製した。Example 13 Example 1 except that the compound (16) is used in the hole transport layer.
A laminated electrophotographic photosensitive member was produced in the same manner as in 2.
【００６３】実施例１４ 正孔輸送層に化合物（１８）を使用する以外は実施例１
２と同様の方法で積層型電子写真感光体を作製した。Example 14 Example 1 except that the compound (18) is used in the hole transport layer.
A laminated electrophotographic photosensitive member was produced in the same manner as in 2.
【００６４】実施例１５ Ｎ，Ｎ’−ビス（２，６−ジクロロフェニル）−３，
４，９，１０−ペリレンジカルボキシイミド２ｇ、ポリ
ビニルブチラール樹脂（ＢＨ−３：積水化学（株）製）
２ｇをテトラヒドロフラン９６ｇと共にボールミルで２
時間分散した。この分散液をアルミニウム基板上に塗
工、乾燥して、膜厚０．３μｍの電荷発生層を作製し
た。次に化合物（１２）１０ｇ、ポリカーボネート樹脂
（Ｌ−１２５０；帝人化成（株）製）１０ｇをジクロロ
メタン８０ｇに溶解した。この塗液を電荷発生層上に塗
工、乾燥して、膜厚２０μｍの正孔輸送層を形成し、図
８に示す積層型電子写真感光体を作製した。Example 15 N, N'-bis (2,6-dichlorophenyl) -3,
2,9,10-Perylenedicarboximide 2g, polyvinyl butyral resin (BH-3: Sekisui Chemical Co., Ltd.)
2g together with 96g of tetrahydrofuran in a ball mill
Time dispersed. This dispersion was applied onto an aluminum substrate and dried to form a charge generation layer having a film thickness of 0.3 μm. Next, 10 g of the compound (12) and 10 g of a polycarbonate resin (L-1250; manufactured by Teijin Chemicals Ltd.) were dissolved in 80 g of dichloromethane. This coating liquid was applied onto the charge generation layer and dried to form a hole transport layer having a film thickness of 20 μm, and the laminated electrophotographic photoreceptor shown in FIG. 8 was produced.
【００６５】電子写真感光体の電子写真特性は以下の方
法で測定した。静電複写紙試験装置（ＥＰＡ−８１０
０；川口電機製作所（株）製）により、スタティックモ
ード２、コロナ帯電は−５．２（ｋＶ）、５（ｌｕｘ）
の白色光を照射して、初期表面電位（Ｖ0）、Ｖ0と２秒
間暗所に放置した時の表面電位（Ｖ2）の比（暗減衰：
ＤＤＲ2＝Ｖ2／Ｖ0）、光露光後に帯電量が初期の１／
２まで減少する時間ら半減露光量感度（Ｅ1/2）および
光露光３秒後の表面電位（ＶＲ3）を調べた実施例７〜
１０の電子写真感光体の電子写真特性を表３に示す。The electrophotographic characteristics of the electrophotographic photosensitive member were measured by the following methods. Electrostatic Copy Paper Testing Device (EPA-810
0; manufactured by Kawaguchi Denki Seisakusho Co., Ltd., static mode 2, corona charging: -5.2 (kV), 5 (lux)
Of the initial surface potential (V 0 ) and V 0 and the surface potential (V 2 ) when left in the dark for 2 seconds (dark decay:
DDR 2 = V 2 / V 0 ), the charge amount after light exposure is 1 / of the initial amount
Examples 7 to 7 in which the half-exposure sensitivity (E 1/2 ) and the surface potential (VR 3 ) after 3 seconds of photoexposure were examined from the time of decreasing to
Table 3 shows the electrophotographic characteristics of the electrophotographic photosensitive member of No. 10.
【００６６】[0066]
【表３】 [Table 3]
【００６７】１万回以上繰り返して電子写真特性を測定
したところ、本実施例で示された全ての電子写真感光体
について、安定な表面電位、感度を得ることができた。When the electrophotographic characteristics were measured repeatedly 10,000 times or more, stable surface potentials and sensitivities could be obtained for all the electrophotographic photosensitive members shown in this example.
【００６８】[0068]
【発明の効果】本発明により、優れた正孔輸送能力を有
する化合物を得ることができた。本発明が提供した化合
物は、従来に比べて高発光効率、高輝度であり、長寿命
の有機ＥＬ素子および感度、正孔輸送特性、初期表面電
位、暗減衰率等の初期電子写真特性に優れ、繰り返し使
用に対する疲労も少ない電子写真感光体を得ることがで
きた。Industrial Applicability According to the present invention, a compound having an excellent hole transporting ability can be obtained. The compound provided by the present invention has higher luminous efficiency, higher brightness, and longer life than conventional organic EL devices and excellent initial electrophotographic properties such as sensitivity, hole transport properties, initial surface potential, and dark decay rate. It was possible to obtain an electrophotographic photosensitive member with little fatigue against repeated use.
【図１】化合物１の赤外吸収スペクトル図FIG. 1 is an infrared absorption spectrum diagram of Compound 1.
【図２】化合物２の赤外吸収スペクトル図FIG. 2 is an infrared absorption spectrum diagram of Compound 2.
【図３】化合物１３の赤外吸収スペクトル図FIG. 3 is an infrared absorption spectrum diagram of Compound 13.
【図４】実施例で使用した有機ＥＬ素子の概略構造を表
す断面図FIG. 4 is a sectional view showing a schematic structure of an organic EL element used in an example.
【図５】実施例で使用した有機ＥＬ素子の概略構造を表
す断面図FIG. 5 is a sectional view showing a schematic structure of an organic EL element used in Examples.
【図６】実施例で使用した有機ＥＬ素子の概略構造を表
す断面図FIG. 6 is a cross-sectional view showing a schematic structure of an organic EL element used in Examples.
【図７】実施例で使用した電子写真感光体の概略構造を
表す断面図FIG. 7 is a sectional view showing a schematic structure of an electrophotographic photosensitive member used in Examples.
【図８】実施例で使用した電子写真感光体の概略構造を
表す断面図FIG. 8 is a sectional view showing a schematic structure of an electrophotographic photosensitive member used in Examples.
１．基板 ２．電極Ａ ３．正孔注入層 ４．発光層 ５．電子注入層 ６．電極Ｂ ７．Ａｌ基板 ８．感光層 ９．電荷発生層 １０．正孔輸送層 1. Substrate 2. Electrode A 3. Hole injection layer 4. Light emitting layer 5. Electron injection layer 6. Electrode B 7. Al substrate 8. Photosensitive layer 9. Charge generation layer 10. Hole transport layer
───────────────────────────────────────────────────── フロントページの続き (72)発明者 小川 但 東京都中央区京橋二丁目３番13号 東洋イ ンキ製造株式会社内 (72)発明者 榎田 年男 東京都中央区京橋二丁目３番13号 東洋イ ンキ製造株式会社内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Tan Ogawa 2-13-3 Kyobashi, Chuo-ku, Tokyo Toyo Inki Manufacturing Co., Ltd. (72) Inventor Toshio Enokada 2-3-3 Kyobashi, Chuo-ku, Tokyo No. Toyo Inki Manufacturing Co., Ltd.
Claims (5)
ルアミン重合体。一般式［１］ 【化１】 ［式中、Ｒ1〜Ｒ3は、それぞれ独立に、水素原子、置換
もしくは未置換のアルキル基、置換もしくは未置換のア
ルコキシ基、置換もしくは未置換のジアルキルアミノ基
である。ｎは、１以上５０００以下の整数である。］1. A triphenylamine polymer represented by the following general formula [1]. General formula [1] [Wherein, R 1 to R 3 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted dialkylamino group. n is an integer of 1 or more and 5000 or less. ]
示されるトリフェニルアミン化合物とを反応させること
を特徴とする請求項１記載のトリフェニルアミン重合体
の製造方法。一般式［２］ 【化２】 ［式中、Ｒ1〜Ｒ3は、それぞれ独立に、水素原子、置換
もしくは未置換のアルキル基、置換もしくは未置換のア
ルコキシ基、置換もしくは未置換のジアルキルアミノ基
である。］2. The method for producing a triphenylamine polymer according to claim 1, wherein cyclohexanone is reacted with a triphenylamine compound represented by the following general formula [2]. General formula [2] [Wherein, R 1 to R 3 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted dialkylamino group. ]
体からなる正孔輸送材料。3. A hole transport material comprising the triphenylamine polymer according to claim 1.
む複数層の有機化合物薄膜を備えた有機エレクトロルミ
ネッセンス素子において、少なくとも一層が請求項３記
載の正孔輸送材料を含有することを特徴とする有機エレ
クトロルミネッセンス素子。4. An organic electroluminescence device comprising a light emitting layer or a plurality of organic compound thin films including a light emitting layer between a pair of electrodes, at least one layer containing the hole transport material according to claim 3. And an organic electroluminescent device.
正孔輸送材料を使用してなる電子写真感光体において、
正孔輸送材料が、請求項３記載の正孔輸送材料であるこ
とを特徴とする電子写真感光体。5. An electrophotographic photoreceptor comprising a charge generating material and a hole transporting material on a conductive support,
An electrophotographic photoreceptor, wherein the hole transport material is the hole transport material according to claim 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17173995A JP3296147B2 (en) | 1994-08-04 | 1995-07-07 | Triphenylamine polymer, its production method and use |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18319894 | 1994-08-04 | ||
| JP6-183198 | 1994-08-04 | ||
| JP17173995A JP3296147B2 (en) | 1994-08-04 | 1995-07-07 | Triphenylamine polymer, its production method and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08100038A true JPH08100038A (en) | 1996-04-16 |
| JP3296147B2 JP3296147B2 (en) | 2002-06-24 |
Family
ID=26494356
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17173995A Expired - Fee Related JP3296147B2 (en) | 1994-08-04 | 1995-07-07 | Triphenylamine polymer, its production method and use |
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0840997A (en) * | 1994-08-04 | 1996-02-13 | Toyo Ink Mfg Co Ltd | New triphenylamine derivative, its production and use |
| JPH0840995A (en) * | 1994-08-04 | 1996-02-13 | Toyo Ink Mfg Co Ltd | New triphenylamine derivative, its production and use |
| JPH0840996A (en) * | 1994-08-04 | 1996-02-13 | Toyo Ink Mfg Co Ltd | New triphenylamine derivative, its production and use |
| JPH1079297A (en) * | 1996-07-09 | 1998-03-24 | Sony Corp | Electroluminescent element |
| JP2002080570A (en) * | 2000-09-07 | 2002-03-19 | Toppan Printing Co Ltd | Electric charge-transferring polymeric material, its production method and electroluminescence element by using the same |
| KR100360317B1 (en) * | 1998-12-07 | 2003-02-19 | 주식회사 만도 | Drill hole processing equipment on the input shaft |
| WO2004014985A1 (en) * | 2002-08-09 | 2004-02-19 | Tosoh Corporation | Novel triarylamine polymer, process for producing the same, and use thereof |
| US6756249B2 (en) | 2001-10-15 | 2004-06-29 | President Of Toyama University | Method of manufacturing organic electroluminescent device |
| JP2004250448A (en) * | 2003-01-30 | 2004-09-09 | Mitsubishi Chemicals Corp | Arylamine based comound, positive hole transferring material and electrophotographic photoreceptor using the same |
| JP2005060387A (en) * | 2003-07-29 | 2005-03-10 | Mitsubishi Chemicals Corp | Manufacturing method of arylamine derivative and methanol derivative used for manufacturing the same |
| KR100565665B1 (en) * | 2004-03-22 | 2006-03-30 | 엘지전자 주식회사 | organic electroluminescence device |
| JP2006316280A (en) * | 2006-06-16 | 2006-11-24 | Konica Minolta Holdings Inc | Material for electroluminescent element |
| US7258932B2 (en) | 2001-07-19 | 2007-08-21 | Sumitomo Chemical Company, Limited | Polymeric fluorescent substrate and polymer light-emitting device using the same |
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Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0840997A (en) * | 1994-08-04 | 1996-02-13 | Toyo Ink Mfg Co Ltd | New triphenylamine derivative, its production and use |
| JPH0840995A (en) * | 1994-08-04 | 1996-02-13 | Toyo Ink Mfg Co Ltd | New triphenylamine derivative, its production and use |
| JPH0840996A (en) * | 1994-08-04 | 1996-02-13 | Toyo Ink Mfg Co Ltd | New triphenylamine derivative, its production and use |
| JPH1079297A (en) * | 1996-07-09 | 1998-03-24 | Sony Corp | Electroluminescent element |
| KR100360317B1 (en) * | 1998-12-07 | 2003-02-19 | 주식회사 만도 | Drill hole processing equipment on the input shaft |
| JP2002080570A (en) * | 2000-09-07 | 2002-03-19 | Toppan Printing Co Ltd | Electric charge-transferring polymeric material, its production method and electroluminescence element by using the same |
| US7258932B2 (en) | 2001-07-19 | 2007-08-21 | Sumitomo Chemical Company, Limited | Polymeric fluorescent substrate and polymer light-emitting device using the same |
| US6756249B2 (en) | 2001-10-15 | 2004-06-29 | President Of Toyama University | Method of manufacturing organic electroluminescent device |
| WO2004014985A1 (en) * | 2002-08-09 | 2004-02-19 | Tosoh Corporation | Novel triarylamine polymer, process for producing the same, and use thereof |
| US7608680B2 (en) | 2002-08-09 | 2009-10-27 | Tosoh Corporation | Triarylamine polymer, process for producing the same, and use thereof |
| JP2004250448A (en) * | 2003-01-30 | 2004-09-09 | Mitsubishi Chemicals Corp | Arylamine based comound, positive hole transferring material and electrophotographic photoreceptor using the same |
| JP2005060387A (en) * | 2003-07-29 | 2005-03-10 | Mitsubishi Chemicals Corp | Manufacturing method of arylamine derivative and methanol derivative used for manufacturing the same |
| KR100565665B1 (en) * | 2004-03-22 | 2006-03-30 | 엘지전자 주식회사 | organic electroluminescence device |
| JP2006316280A (en) * | 2006-06-16 | 2006-11-24 | Konica Minolta Holdings Inc | Material for electroluminescent element |
| WO2011065395A1 (en) * | 2009-11-25 | 2011-06-03 | 日産化学工業株式会社 | Carbon nano-tube dispersant |
| US9123893B2 (en) | 2009-11-25 | 2015-09-01 | Nissan Chemical Industries, Ltd. | Carbon nano-tube dispersant |
| CN104030995A (en) * | 2014-06-19 | 2014-09-10 | 孔庆刚 | Hole-transporting material with main body big ring and multiple-lateral branch triphenylamine built by triphenylamine |
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