JP2003089682A - Amine compound and organic electroluminescence element comprising the same - Google Patents
Amine compound and organic electroluminescence element comprising the sameInfo
- Publication number
- JP2003089682A JP2003089682A JP2001285020A JP2001285020A JP2003089682A JP 2003089682 A JP2003089682 A JP 2003089682A JP 2001285020 A JP2001285020 A JP 2001285020A JP 2001285020 A JP2001285020 A JP 2001285020A JP 2003089682 A JP2003089682 A JP 2003089682A
- Authority
- JP
- Japan
- Prior art keywords
- group
- layer
- amine compound
- light emitting
- aniline
- 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
- -1 Amine compound Chemical class 0.000 title claims abstract description 320
- 238000005401 electroluminescence Methods 0.000 title abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 abstract description 64
- 239000000463 material Substances 0.000 abstract description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 193
- 239000010410 layer Substances 0.000 description 186
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 136
- 238000007740 vapor deposition Methods 0.000 description 43
- 239000000758 substrate Substances 0.000 description 37
- 238000000034 method Methods 0.000 description 31
- 238000002347 injection Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- 229910052782 aluminium Inorganic materials 0.000 description 17
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 238000000151 deposition Methods 0.000 description 14
- 230000008021 deposition Effects 0.000 description 13
- 239000013078 crystal Substances 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 10
- 239000007772 electrode material Substances 0.000 description 10
- 239000011777 magnesium Substances 0.000 description 10
- 229910052749 magnesium Inorganic materials 0.000 description 10
- 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 10
- 239000007983 Tris buffer Substances 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 8
- 239000004332 silver Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- OWWVTWHBNAWUJO-UHFFFAOYSA-N 4-iodo-n,n-diphenylaniline Chemical compound C1=CC(I)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 OWWVTWHBNAWUJO-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 7
- UWAZNSFCLKBMAE-UHFFFAOYSA-N [6-(n-phenylanilino)naphthalen-2-yl]boronic acid Chemical compound C1=CC2=CC(B(O)O)=CC=C2C=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UWAZNSFCLKBMAE-UHFFFAOYSA-N 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000004140 cleaning Methods 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000002356 single layer Substances 0.000 description 7
- 229910021642 ultra pure water Inorganic materials 0.000 description 7
- 239000012498 ultrapure water Substances 0.000 description 7
- IPBDNFDRRAAXFX-UHFFFAOYSA-N 6-bromo-n,n-diphenylnaphthalen-2-amine Chemical compound C1=CC2=CC(Br)=CC=C2C=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 IPBDNFDRRAAXFX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000002524 organometallic group Chemical group 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229940126142 compound 16 Drugs 0.000 description 5
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 5
- 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 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000123 polythiophene Polymers 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 125000005259 triarylamine group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229940127573 compound 38 Drugs 0.000 description 4
- 229940125936 compound 42 Drugs 0.000 description 4
- DYGBNAYFDZEYBA-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[4-(4-methoxybenzoyl)piperidin-1-yl]-n-[(4-oxo-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-2-yl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(CC(=O)N(CC2CC2)CC=2NC(=O)C=3COCCC=3N=2)CC1 DYGBNAYFDZEYBA-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011241 protective layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 3
- 229910052790 beryllium Inorganic materials 0.000 description 3
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 235000001671 coumarin Nutrition 0.000 description 3
- 229960000956 coumarin Drugs 0.000 description 3
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Chemical compound O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 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 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- WGWZJNILGYTDHU-UHFFFAOYSA-K tris(3,5-dimethylphenoxy)alumane Chemical compound CC=1C=C([O-])C=C(C1)C.[Al+3].CC=1C=C([O-])C=C(C1)C.CC=1C=C([O-])C=C(C1)C WGWZJNILGYTDHU-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、新規なアミン化合
物および該アミン化合物を含有してなる有機電界発光素
子に関する。TECHNICAL FIELD The present invention relates to a novel amine compound and an organic electroluminescent device containing the amine compound.
【０００２】[0002]
【従来の技術】従来、アミン化合物は各種色素の製造中
間体、あるいは各種の機能材料として使用されてきた。2. Description of the Related Art Conventionally, amine compounds have been used as intermediates for producing various dyes or various functional materials.
【０００３】機能材料としては、例えば、電子写真感光
体の電荷輸送材料に使用されてきた。最近では、発光材
料に有機材料を用いた有機電界発光素子（有機エレクト
ロルミネッセンス素子：有機ＥＬ素子）の正孔注入輸送
材料として有用であることが提案されている〔例えば、
Appl.Phys.lett.,51,913（1987）〕。As a functional material, for example, a charge transport material for an electrophotographic photoreceptor has been used. Recently, it has been proposed that it is useful as a hole injecting and transporting material for an organic electroluminescent device (organic electroluminescent device: organic EL device) using an organic material as a light emitting material [eg,
Appl.Phys.lett., 51 , 913 (1987)].
【０００４】有機電界発光素子は蛍光性有機化合物を含
む薄膜を、陽極と陰極間に挟持した構造を有し、該薄膜
に電子および正孔（ホール）を注入して、再結合させる
ことにより励起子（エキシントン）を生成させ、この励
起子が失活する際に放出される光を利用して発光する素
子である。有機電界発光素子は、数Ｖ〜数十Ｖ程度の直
流の低電圧で発光が可能であり、また、蛍光性有機化合
物の種類を選択することにより、種々の色（例えば、赤
色、青色、緑色）の発光が可能である。このような特徴
を有する有機電界発光素子は種々の発光素子、表示素子
等への応用が期待されている。しかしながら、一般に、
有機電界発光素子は、安定性、耐久性に乏しいなどの欠
点を有している。有機電界発光素子の蛍光性有機化合物
を含む薄膜への正孔の注入輸送を効率よく行う目的で、
正孔注入輸送材料として、４，４’−ビス〔Ｎ−フェニ
ル−Ｎ−（３”−メチルフェニル）アミノ〕ビフェニル
を用いることが提案されている〔Jpn.J.Appl.Phys.,2
7，L269(1988)〕。The organic electroluminescence device has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode, and electrons and holes are injected into the thin film to excite them by recombining. This element emits light by using the light emitted when an exciton is deactivated by generating a child (exington). The organic electroluminescence device can emit light at a low DC voltage of about several V to several tens of V. Further, by selecting the type of the fluorescent organic compound, various colors (for example, red, blue, green) can be obtained. ) Is possible. The organic electroluminescent device having such characteristics is expected to be applied to various light emitting devices, display devices and the like. However, in general,
Organic electroluminescent devices have drawbacks such as poor stability and durability. In order to efficiently inject and transport holes into a thin film containing a fluorescent organic compound of an organic electroluminescence device,
It has been proposed to use 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl as a hole injecting and transporting material [Jpn.J.Appl.Phys., 2
7 , L269 (1988)].
【０００５】また、正孔注入輸送材料として、例えば、
９，９−ジアルキル−２，７−ビス（Ｎ，Ｎ−ジフェニ
ルアミノ）フルオレン誘導体〔例えば、９，９−ジメチ
ル−２，７−ビス（Ｎ，Ｎ−ジフェニルアミノ）フルオ
レン〕を用いることも提案されている（特開平５−２５
４７３号公報）。As the hole injecting and transporting material, for example,
It is also proposed to use 9,9-dialkyl-2,7-bis (N, N-diphenylamino) fluorene derivative [for example, 9,9-dimethyl-2,7-bis (N, N-diphenylamino) fluorene]. (Japanese Patent Laid-Open No. 5-25
473).
【０００６】しかしながら、これらのアミン化合物を正
孔注入輸送材料として使用した有機電界発光素子も、安
定性、耐久性に乏しいなどの難点があった。However, the organic electroluminescence device using these amine compounds as the hole injecting and transporting material also has drawbacks such as poor stability and durability.
【０００７】現在では、安定性、耐久性に優れた有機電
界発光素子が求められており、そのため、有機電界発光
素子として使用した際に優れた特性を示す新規なアミン
化合物が望まれている。At present, there is a demand for an organic electroluminescent device having excellent stability and durability, and therefore, a novel amine compound exhibiting excellent properties when used as an organic electroluminescent device is desired.
【０００８】[0008]
【発明が解決しようとする課題】本発明の課題は、新規
なアミン化合物および該化合物を含有する有機電界発光
素子を提供することである。さらに詳しくは、有機電界
発光素子の正孔注入輸送材料等に適した新規なアミン化
合物、および該アミン化合物を使用した、安定性、耐久
性に優れた有機電界発光素子を提供することである。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel amine compound and an organic electroluminescence device containing the compound. More specifically, the present invention provides a novel amine compound suitable as a hole injecting / transporting material of an organic electroluminescent device, and an organic electroluminescent device using the amine compound, which is excellent in stability and durability.
【０００９】[0009]
【課題を解決するための手段】本発明者らは、上記課題
を解決するために、種々のアミン化合物および有機電界
発光素子に関して鋭意検討を行った結果、本発明を完成
させるに至った。すなわち、本発明は、一般式（１）
（化２）で表されるアミン化合物、In order to solve the above problems, the inventors of the present invention have conducted extensive studies on various amine compounds and organic electroluminescent devices, and as a result, have completed the present invention. That is, the present invention has the general formula (1)
An amine compound represented by (Chemical Formula 2),
【００１０】[0010]
【化２】
〔式中、Ａｒ1、Ａｒ2、Ａｒ3およびＡｒ4は置換または
未置換のアリール基を表し、Ｒ1、Ｒ2、Ｒ3、Ｒ4、
Ｒ5、Ｒ6、Ｒ7、Ｒ8、Ｒ9およびＲ10は、水素原子、ハ
ロゲン原子または−（Ｏ）ｎ−Ｚ基（式中Ｚは、ハロゲ
ン原子で置換されていてもよい直鎖、分岐または環状の
アルキル基、あるいは置換または未置換のアリール基を
表し、ｎは０または１を表す）を表す〕[Chemical 2] [Wherein Ar 1 , Ar 2 , Ar 3 and Ar 4 represent a substituted or unsubstituted aryl group, and R 1 , R 2 , R 3 , R 4 and
R 5, R 6, R 7 , R 8, R 9 and R 10 are a hydrogen atom, a halogen atom or - (O) n-Z group (wherein Z is optionally straight optionally substituted by a halogen atom , A branched or cyclic alkyl group, or a substituted or unsubstituted aryl group, and n represents 0 or 1).
【００１１】 一般式（１）で表されるアミン化合物
においてＡｒ1、Ａｒ2、Ａｒ3およびＡｒ4の内、少なく
とも一つがフェニル基である記載のアミン化合物、
一対の電極間に一般式（１）で表されるアミン化合物
を少なくとも１種含有する層を少なくとも一層挟持して
なる有機電界発光素子、
一般式（１）で表されるアミン化合物を含有する層
が、正孔注入輸送層である記載の有機電界発光素子、
一般式（１）で表されるアミン化合物を含有する層
が、発光層である記載の有機電界発光素子、
一対の電極間に、さらに、発光層を有する前記また
は記載の有機電界発光素子、
一対の電極間に、さらに、電子注入輸送層を有する前
記〜のいずれかに記載の有機電界発光素子、に関す
るものである。In the amine compound represented by the general formula (1), at least one of Ar 1 , Ar 2 , Ar 3 and Ar 4 is a phenyl group, the amine compound described in the general formula (1 ) An organic electroluminescent device in which at least one layer containing at least one amine compound represented by the formula (1) is sandwiched, and the layer containing the amine compound represented by the general formula (1) is a hole injecting and transporting layer. The organic electroluminescent device according to claim 1, the organic electroluminescent device according to claim 1, wherein the layer containing the amine compound represented by the general formula (1) is a luminescent layer, and the above or the description further including a luminescent layer between a pair of electrodes. And the organic electroluminescent element according to any one of 1 to 3, further comprising an electron injecting and transporting layer between a pair of electrodes.
【００１２】[0012]
【発明の実施の形態】以下、本発明に関し詳細に説明す
る。本発明のアミン化合物は一般式（１）（化３）で表
される化合物である。BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below. The amine compound of the present invention is a compound represented by the general formula (1) (formula 3).
【００１３】[0013]
【化３】
〔式中、Ａｒ1、Ａｒ2、Ａｒ3およびＡｒ4は置換または
未置換のアリール基を表し、Ｒ1、Ｒ2、Ｒ3、Ｒ4、
Ｒ5、Ｒ6、Ｒ7、Ｒ8、Ｒ9およびＲ10は、水素原子、ハ
ロゲン原子または−（Ｏ）ｎ−Ｚ基（式中Ｚは、ハロゲ
ン原子で置換されていてもよい直鎖、分岐または環状の
アルキル基、あるいは置換または未置換のアリール基を
表し、ｎは０または１を表す）を表す〕[Chemical 3] [Wherein Ar 1 , Ar 2 , Ar 3 and Ar 4 represent a substituted or unsubstituted aryl group, and R 1 , R 2 , R 3 , R 4 and
R 5, R 6, R 7 , R 8, R 9 and R 10 are a hydrogen atom, a halogen atom or - (O) n-Z group (wherein Z is optionally straight optionally substituted by a halogen atom , A branched or cyclic alkyl group, or a substituted or unsubstituted aryl group, and n represents 0 or 1).
【００１４】一般式（１）で表されるアミン化合物にお
いて、Ａｒ1、Ａｒ2、Ａｒ3およびＡｒ4は、好ましく
は、未置換、もしくは、置換基として、例えば、ハロゲ
ン原子、アルキル基、アルコキシ基、あるいはアリール
基で単置換または多置換されてもよい総炭素数６〜２０
の炭素環式芳香族化合物または総炭素数３〜２０の複素
環式芳香族基であり、より好ましくは、未置換、もしく
は、ハロゲン原子、炭素数１〜１４のアルキル基、炭素
数１〜１４のアルコキシ基、あるいは炭素数６〜１０の
アリール基で単置換または多置換されていてもよい総炭
素数６〜２０の炭素環式芳香族基であり、さらに好まし
くは、未置換、もしくは、ハロゲン原子、炭素数１〜４
のアルキル基、炭素数１〜４のアルコキシ基、あるいは
炭素数６〜１０のアリール基で単置換あるいは多置換さ
れていてもよい総炭素数６〜１６の炭素環式芳香族基で
ある。In the amine compound represented by the general formula (1), Ar 1 , Ar 2 , Ar 3 and Ar 4 are preferably unsubstituted or as a substituent, for example, a halogen atom, an alkyl group or an alkoxy group. 6-20 total carbon atoms which may be mono- or poly-substituted with a group or an aryl group
Is a carbocyclic aromatic compound or a heterocyclic aromatic group having 3 to 20 carbon atoms in total, more preferably unsubstituted, a halogen atom, an alkyl group having 1 to 14 carbon atoms, or 1 to 14 carbon atoms. Is a carbocyclic aromatic group having a total of 6 to 20 carbon atoms which may be mono- or poly-substituted with an alkoxy group of 6 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, more preferably an unsubstituted or halogen atom. Atom, carbon number 1-4
Is an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a carbocyclic aromatic group having 6 to 16 carbon atoms which may be mono- or polysubstituted.
【００１５】Ａｒ1、Ａｒ2、Ａｒ3およびＡｒ4の具体例
としては、例えば、フェニル基、１−ナフチル基、２−
ナフチル基、２−アントラセニル基、９−アントラセニ
ル基，４−キノリニル基、１−ピレニル基、４−ピリジ
ニル基、３−ピリジニル基、２−ピリジニル基、３−フ
ラニル基、２−フラニル基、３−チエニル基、２−チエ
ニル基、２−オキサゾリル基、２−チアゾリル基、２−
ベンゾオキサゾリル基、２−ベンゾチアゾリル基、２−
ベンゾイミダゾリル基、４−メチルフェニル基、３−メ
チルフェニル基、２−メチルフェニル基、４−エチルフ
ェニル基、３−エチルフェニル基、２−エチルフェニル
基、４−ｎ−プロピルフェニル基、４−イソプロピルフ
ェニル基、２−イソプロピルフェニル基、４−ｎ−ブチ
ルフェニル基、４−イソブチルフェニル基、４−sec−
ブチルフェニル基、２−sec−ブチルフェニル基、４−t
ert−ブチルフェニル基、３−tert−ブチルフェニル
基、２−tertブチルフェニル基、４−ｎ−ペンチルフェ
ニル基、４−イソペンチルフェニル基、２−ネオペンチ
ルフェニル基、４−tert−ペンチルフェニル基、４−ｎ
−ヘキシルフェニル基、４−（２’−エチルブチル）フ
ェニル基、４−ｎ−ヘプチルフェニル基、４−ｎ−オク
チルフェニル基、４−（２’−エチルヘキシル）フェニ
ル基、４−tert−オクチルフェニル基、４−ｎ−デシル
フェニル基、４−ｎ−ドデシルフェニル基、４−ｎ−テ
トラデシルフェニル基、４−シクロペンチルフェニル
基、４−シクロヘキシルフェニル基、４−（４’−メチ
ルシクロヘキシル）フェニル基、４−（４’−tert−ブ
チルシクロヘキシル）フェニル基、３−シクロヘキシル
フェニル基、２−シクロヘキシルフェニル基、４−エチ
ル−１−ナフチル基、６−ｎ−ブチル−２−ナフチル
基、２，４−ジメチルフェニル基、３，５−ジメチルフ
ェニル基、２，６−ジメチルフェニル基、２，４−ジエ
チルフェニル基、２，３，５−トリメチルフェニル基、
２，３，６−トリメチルフェニル基、３，４，５−トリ
メチルフェニル基、２，６−ジエチルフェニル基、Specific examples of Ar 1 , Ar 2 , Ar 3 and Ar 4 include, for example, phenyl group, 1-naphthyl group, 2-
Naphthyl group, 2-anthracenyl group, 9-anthracenyl group, 4-quinolinyl group, 1-pyrenyl group, 4-pyridinyl group, 3-pyridinyl group, 2-pyridinyl group, 3-furanyl group, 2-furanyl group, 3- Thienyl group, 2-thienyl group, 2-oxazolyl group, 2-thiazolyl group, 2-
Benzoxazolyl group, 2-benzothiazolyl group, 2-
Benzimidazolyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropyl Phenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-
Butylphenyl group, 2-sec-butylphenyl group, 4-t
ert-butylphenyl group, 3-tert-butylphenyl group, 2-tertbutylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 2-neopentylphenyl group, 4-tert-pentylphenyl group , 4-n
-Hexylphenyl group, 4- (2'-ethylbutyl) phenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4- (2'-ethylhexyl) phenyl group, 4-tert-octylphenyl group , 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4- (4'-methylcyclohexyl) phenyl group, 4- (4'-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 2,4- Dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,4-diethylphenyl group, 2,3,5- Trimethyl phenyl group,
2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl group, 2,6-diethylphenyl group,
【００１６】２，５−ジイソプロピルフェニル基、２，
６−ジイソブチルフェニル基、２，４−ジ−tert−ブチ
ルフェニル基、２，５−ジ−tert−ブチルフェニル基、
４，６−ジ−tert−ブチル−２−メチルフェニル基、５
−tert−ブチル−２−メチルフェニル基、４−tert−ブ
チル−２，６−ジメチルフェニル基、４−メトキシフェ
ニル基、３−メトキシフェニル基、２−メトキシフェニ
ル基、４−エトキシフェニル基、３−エトキシフェニル
基、２−エトキシフェニル基、４−ｎ−プロポキシフェ
ニル基、３−ｎ−プロポキシフェニル基、４−イソプロ
ポキシフェニル基、３−イソプロポキシフェニル基、２
−イソプロポキシフェニル基、４−ｎ−ブトキシフェニ
ル基、４−イソブトキシフェニル基、２−sec−ブトキ
シフェニル基、４−ｎ−ペンチルオキシフェニル基、４
−イソペンチルオキシフェニル基、２−イソペンチルオ
キシフェニル基、４−ネオペンチルオキシフェニル基、
２−ネペンチルオキシフェニル基、４−ｎ−ヘキシルオ
キシフェニル基、２−（２’−エチルブチルオキシ）フ
ェニル基、４−ｎ−オクチルオキシフェニル基、４−ｎ
−デシルオキシフェニル基、４−ｎ−ドデシルオキシフ
ェニル基、４−ｎ−テトラデシルオキシフェニル基、４
−シクロヘキシルオキシフェニル基、２−シクロヘキシ
ルオキシフェニル基、２−メトキシ−１−ナフチル基、
４−メトキシ−１−ナフチル基、４−ｎ−ブトキシ−１
−ナフチル基、５−エトキシ−１−ナフチル基、６−メ
トキシ−２−ナフチル基、６−エトキシ−２−ナフチル
基、６−ｎ−ブトキシ−２−ナフチル基、６−ｎ−ヘキ
シルオキシ−２−ナフチル基、７−メトキシ−２−ナフ
チル基、７−ｎ−ブトキシ−２−ナフチル基、２−メチ
ル−４−メトキシフェニル基、２−メチル−５−メトキ
シフェニル基、３−メチル−５−メトキシフェニル基、
３−エチル−５−メトキシフェニル基、２−メトキシ−
４−メチルフェニル基、３−メトキシ−４−メチルフェ
ニル基、２，４−ジメトキシフェニル基、２，５−ジメ
トキシフェニル基、２，６−ジメトキシフェニル基、
３，４−ジメトキシフェニル基、３，５−ジメトキシフ
ェニル基、３，５−ジエトキシフェニル基、３，５−ジ
−ｎ−ブトキシフェニル基、２−メトキシ−４−エトキ
シフェニル基、２−メトキシ−６−エトキシフェニル
基、３，４，５−トリメトキシフェニル基、４−フェニ
ルフェニル基、2,5-diisopropylphenyl group, 2,
6-diisobutylphenyl group, 2,4-di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group,
4,6-di-tert-butyl-2-methylphenyl group, 5
-Tert-butyl-2-methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 3 -Ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 3-isopropoxyphenyl group, 2
-Isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4
-Isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyloxyphenyl group,
2-nepentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2'-ethylbutyloxy) phenyl group, 4-n-octyloxyphenyl group, 4-n
-Decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group, 4
-Cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2-methoxy-1-naphthyl group,
4-methoxy-1-naphthyl group, 4-n-butoxy-1
-Naphthyl group, 5-ethoxy-1-naphthyl group, 6-methoxy-2-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n-butoxy-2-naphthyl group, 6-n-hexyloxy-2 -Naphthyl group, 7-methoxy-2-naphthyl group, 7-n-butoxy-2-naphthyl group, 2-methyl-4-methoxyphenyl group, 2-methyl-5-methoxyphenyl group, 3-methyl-5- Methoxyphenyl group,
3-ethyl-5-methoxyphenyl group, 2-methoxy-
4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group,
3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy -6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-phenylphenyl group,
【００１７】３−フェニルフェニル基、２−フェニルフ
ェニル基、４−（４’−メチルフェニル）フェニル基、
４−（３’−メチルフェニル）フェニル基、４−（４’
−メトキシフェニル）フェニル基、４−（４’−ｎ−ブ
トキシフェニル）フェニル基、２−（２’−メトキシフ
ェニル）フェニル基、４−（４’−クロロフェニル）フ
ェニル基、３−メチル−４−フェニルフェニル基、３−
メトキシ−４−フェニルフェニル基、４−フルオロフェ
ニル基、３−フルオロフェニル基、２−フルオロフェニ
ル基、４−クロロフェニル基、３−クロロフェニル基、
２−クロロフェニル基、４−ブロモフェニル基、３−ブ
ロモフェニル基、２−ブロモフェニル基、４−クロロ−
１−ナフチル基、４−クロロ−２−ナフチル基、６−ブ
ロモ−２−ナフチル基、２，３−ジフルオロフェニル
基、２，５−ジフルオロフェニル基、２，６−ジフルオ
ロフェニル基、３，４−ジフルオロフェニル基、３，５
−ジフルオロフェニル基、２，３−ジクロロフェニル
基、２，４−ジクロロフェニル基、２，５−ジクロロフ
ェニル基、３，４−ジクロロフェニル基、３，５−ジク
ロロフェニル基、２，５−ジブロモフェニル基、２，
４，６−トリクロロフェニル基、２，４−ジクロロ−１
−ナフチル基、１，６−ジクロロ−２−ナフチル基、3-phenylphenyl group, 2-phenylphenyl group, 4- (4'-methylphenyl) phenyl group,
4- (3'-methylphenyl) phenyl group, 4- (4 '
-Methoxyphenyl) phenyl group, 4- (4'-n-butoxyphenyl) phenyl group, 2- (2'-methoxyphenyl) phenyl group, 4- (4'-chlorophenyl) phenyl group, 3-methyl-4- Phenylphenyl group, 3-
Methoxy-4-phenylphenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group,
2-chlorophenyl group, 4-bromophenyl group, 3-bromophenyl group, 2-bromophenyl group, 4-chloro-
1-naphthyl group, 4-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 2,3-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4 -Difluorophenyl group, 3,5
-Difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,5-dibromophenyl group, 2,
4,6-trichlorophenyl group, 2,4-dichloro-1
-Naphthyl group, 1,6-dichloro-2-naphthyl group,
【００１８】２−フルオロ−４−メチルフェニル基、２
−フルオロ−５−メチルフェニル基、３−フルオロ−２
−メチルフェニル基、３−フルオロ−４−メチルフェニ
ル基、２−メチル−４−フルオロフェニル基、２−メチ
ル−５−フルオロフェニル基、３−メチル−４−フルオ
ロフェニル基、２−クロロ−４−メチルフェニル基、２
−クロロ−４−メチルフェニル基、２−クロロ−５−メ
チルフェニル基、２−クロロ−６−メチルフェニル基、
２−メチル−３−クロロフェニル基、２−メチル−３−
クロロフェニル基、２−メチル−４−クロロフェニル
基、３−メチル−４−クロロフェニル基、２−クロロ−
４，６−ジメチルフェニル基、２−メトキシ−４−フル
オロフェニル基、２−フルオロ−４−メトキシフェニル
基、２−フルオロ−４−エトキシフェニル基、２−フル
オロ−６−メトキシフェニル基、３−フルオロ−４−エ
トキシフェニル基、３−クロロ−４−メトキシフェニル
基、２−メトキシ−５−クロロフェニル基、３−メトキ
シ−６−クロロフェニル基、５−クロロ−２，４−ジメ
トキシフェニル基を挙げることができるが、これらに限
定されるものではない。2-fluoro-4-methylphenyl group, 2
-Fluoro-5-methylphenyl group, 3-fluoro-2
-Methylphenyl group, 3-fluoro-4-methylphenyl group, 2-methyl-4-fluorophenyl group, 2-methyl-5-fluorophenyl group, 3-methyl-4-fluorophenyl group, 2-chloro-4 -Methylphenyl group, 2
-Chloro-4-methylphenyl group, 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group,
2-methyl-3-chlorophenyl group, 2-methyl-3-
Chlorophenyl group, 2-methyl-4-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-
4,6-dimethylphenyl group, 2-methoxy-4-fluorophenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-4-ethoxyphenyl group, 2-fluoro-6-methoxyphenyl group, 3- Fluoro-4-ethoxyphenyl group, 3-chloro-4-methoxyphenyl group, 2-methoxy-5-chlorophenyl group, 3-methoxy-6-chlorophenyl group, 5-chloro-2,4-dimethoxyphenyl group. However, the present invention is not limited to these.
【００１９】一般式（１）で表されるアミン化合物にお
いて、Ａｒ1〜Ａｒ4は、それぞれが同種であってもよ
く、また、すべてが異なっていても良い。一般式（１）
で表されるアミン化合物においてＡｒ1、Ａｒ2、Ａｒ3
およびＡｒ4は、少なくとも一つがフェニル基であるこ
とが好ましい。In the amine compound represented by the general formula (1), Ar 1 to Ar 4 may be the same or different from each other. General formula (1)
Ar 1 , Ar 2 , Ar 3 in the amine compound represented by
At least one of Ar 4 and Ar 4 is preferably a phenyl group.
【００２０】一般式（１）で表されるアミン化合物にお
いて、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5、Ｒ6、Ｒ7、Ｒ8、Ｒ9
およびＲ10は水素原子、ハロゲン原子または−（Ｏ）ｎ
−Ｚ基（式中Ｚは、ハロゲン原子で置換されていてもよ
い直鎖、分岐または環状のアルキル基、あるいは置換ま
たは未置換のアリール基を表し、ｎは０または１を表
す）を表し、好ましくは、水素原子、ハロゲン原子また
は−（Ｏ）ｎ−Ｚ基（式中Ｚは、ハロゲン原子で置換さ
れていてもよい炭素数１〜１６の直鎖、分岐または環状
のアルキル基、あるいは置換または未置換の炭素数４〜
１２のアリール基を表し、ｎは０または１を表す）を表
し、より好ましくは、水素原子、ハロゲン原子または−
（Ｏ）ｎ−Ｚ基（式中Ｚは、ハロゲン原子で置換されて
いてもよい炭素数１〜８の直鎖、分岐または環状のアル
キル基、あるいは置換または未置換の炭素数６〜１２の
アリール基を表し、ｎは０または１を表す）を表し、さ
らに好ましくは、水素原子、ハロゲン原子、炭素数１〜
８の直鎖、分岐鎖または環状のアルキル基、炭素数６〜
１０の炭素環式芳香族基を表す。In the amine compound represented by the general formula (1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9
And R 10 is a hydrogen atom, a halogen atom or — (O) n.
A -Z group (in the formula, Z represents a linear, branched or cyclic alkyl group which may be substituted with a halogen atom, or a substituted or unsubstituted aryl group, and n represents 0 or 1), Preferably, a hydrogen atom, a halogen atom or a-(O) n-Z group (in the formula, Z is a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms which may be substituted with a halogen atom, or a substituent). Or an unsubstituted carbon number 4 to
12 represents an aryl group, and n represents 0 or 1), more preferably a hydrogen atom, a halogen atom or-.
(O) n-Z group (wherein Z is a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms which may be substituted with a halogen atom, or a substituted or unsubstituted C 6 to 12 carbon atom) Represents an aryl group, n represents 0 or 1, and more preferably a hydrogen atom, a halogen atom, or a carbon number of 1 to 1.
8 straight chain, branched chain or cyclic alkyl group, having 6 to 6 carbon atoms
Represents 10 carbocyclic aromatic groups.
【００２１】尚、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5、Ｒ6、
Ｒ7、Ｒ8、Ｒ9およびＲ10の（Ｏ）ｎ−Ｚ基のＺである
置換または未置換のアリール基の具体例としては、例え
ば、Ａｒ 1、Ａｒ2、Ａｒ3およびＡｒ4の具体例として挙
げた置換または未置換のアリール基を挙げることができ
る。Incidentally, R1, R2, R3, RFour, RFive, R6,
R7, R8, R9And RTenIs Z of the (O) n-Z group of
Specific examples of the substituted or unsubstituted aryl group include
For example, Ar 1, Ar2, Ar3And ArFourAs a concrete example of
A substituted or unsubstituted aryl group.
It
【００２２】Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5、Ｒ6、Ｒ7、
Ｒ8、Ｒ9およびＲ10の（Ｏ）ｎ−Ｚ基のＺである直鎖、
分岐または環状のアルキル基の具体例としては、例え
ば、メチル基、エチル基、ｎ−プロピル基、イソプロピ
ル基、ｎ−ブチル基、イソブチル基、sec−ブチル基、t
ert−ブチル基、ｎ−ペンチル基、イソペンチル基、ネ
オペンチル基、tert−ペンチル基、シクロペンチル基、
ｎ−ヘキシル基、シクロペンチルメチル基、２−エチル
ブチル基、３，３−ジメチルブチル基、シクロヘキシル
基、ｎ−ヘプチル基、シクロヘキルメチル基、シクロペ
ンチルエチル基、ｎ−オクチル基、tert−オクチル基、
２−エチルヘキシル基、ｎ−ノニル基、シクロヘキシル
エチル基、ｎ−デシル基、ｎ−ドデシル基、ｎ−テトラ
デシル基、ｎ−ヘキサデシル基等のハロゲン原子で置換
されていない直鎖、分岐鎖または環状のアルキル基、R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 ,
A straight chain which is Z of the (O) n-Z group of R 8 , R 9 and R 10 .
Specific examples of the branched or cyclic alkyl group include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t
ert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, cyclopentyl group,
n-hexyl group, cyclopentylmethyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, cyclohexyl group, n-heptyl group, cyclohexylmethyl group, cyclopentylethyl group, n-octyl group, tert-octyl group,
2-ethylhexyl group, n-nonyl group, cyclohexylethyl group, n-decyl group, n-dodecyl group, n-tetradecyl group, n-hexadecyl group, etc., which is not substituted with a halogen atom, and is straight-chain, branched or cyclic. An alkyl group,
【００２３】フルオロメチル基、ジフルオロメチル基、
トリフルオロメチル基、２−フルオロエチル基、２，２
−ジフルオロエチル基、２，２，２−トリフルオロエチ
ル基、２−フルオロ−ｎ−プロピル基、３−フルオロ−
ｎ−プロピル基、１，３−ジフルオロ−ｎ−プロピル
基、２，３−ジフルオロ−ｎ−プロピル基、２−フルオ
ロ−ｎ−ブチル基、３−フルオロ−ｎ−ブチル基、４−
フルオロ−ｎ−ブチル基、３−フルオロ−２−メチルプ
ロピル基、２，３−ジフルオロ−ｎ−ブチル基、２，４
−ジフルオロ−ｎ−ブチル基、３，４−ジフルオロ−ｎ
−ブチル基、２−フルオロ−ｎ−ペンチル基、３−フル
オロ−ｎ−ペンチル基、５−フルオロ−ｎ−ペンチル
基、２，４−ジフルオロ−ｎ−ペンチル基、２，５−ジ
フルオロ−ｎ−ペンチル基、２−フルオロ−３−メチル
ブチル基、２−フルオロ−ｎ−ヘキシル基、３−フルオ
ロ−ｎ−ヘキシル基、４−フルオロ−ｎ−ヘキシル基、
５−フルオロ−ｎ−ヘキシル基、６−フルオロ−ｎ−ヘ
キシル基、Fluoromethyl group, difluoromethyl group,
Trifluoromethyl group, 2-fluoroethyl group, 2,2
-Difluoroethyl group, 2,2,2-trifluoroethyl group, 2-fluoro-n-propyl group, 3-fluoro-
n-propyl group, 1,3-difluoro-n-propyl group, 2,3-difluoro-n-propyl group, 2-fluoro-n-butyl group, 3-fluoro-n-butyl group, 4-
Fluoro-n-butyl group, 3-fluoro-2-methylpropyl group, 2,3-difluoro-n-butyl group, 2,4
-Difluoro-n-butyl group, 3,4-difluoro-n
-Butyl group, 2-fluoro-n-pentyl group, 3-fluoro-n-pentyl group, 5-fluoro-n-pentyl group, 2,4-difluoro-n-pentyl group, 2,5-difluoro-n- Pentyl group, 2-fluoro-3-methylbutyl group, 2-fluoro-n-hexyl group, 3-fluoro-n-hexyl group, 4-fluoro-n-hexyl group,
5-fluoro-n-hexyl group, 6-fluoro-n-hexyl group,
【００２４】２−フルオロ−ｎ−ヘプチル基、４−フル
オロ−ｎ−ヘプチル基、５−フルオロ−ｎ−ヘプチル
基、２−フルオロ−ｎ−オクチル基、３−フルオロ−ｎ
−オクチル基、６−フルオロ−ｎ−オクチル基、４−フ
ルオロ−ｎ−ノニル基、７−フルオロ−ｎ−ノニル基、
３−フルオロ−ｎ−デシル基、６−フルオロ−ｎ−デシ
ル基、４−フルオロ−ｎ−ドデシル基、８−フルオロ−
ｎ−ドデシル基、５−フルオロ−ｎ−テトラデシル基、
９−フルオロ−ｎ−テトラデシル基、クロロメチル基、
ジクロロメチル基、トリクロロメチル基、２−クロロエ
チル基、２，２−ジクロロエチル基、２，２，２−トリ
クロロエチル基、２，２，２，１−テトラクロロエチル
基、３−クロロ−ｎ−プロピル基、２−クロロ−ｎ−ブ
チル基、４−クロロ−ｎ−ブチル基、２−クロロ−ｎ−
ペンチル基、５−クロロ−ｎ−ペンチル基、５−クロロ
−ｎ−ヘキシル基、４−クロロ−ｎ−ヘプチル基、６−
クロロ−ｎ−オクチル基、７−クロロ−ｎ−ノニル基、
３−クロロ−ｎ−デシル基、８−クロロ−ｎ−ドデシル
基、パーフルオロエチル基、ｎ−パーフルオロプロピル
基、ｎ−パーフルオロブチル基、ｎ−パーフルオロペン
チル基、ｎ−パーフルオロヘキシル基、ｎ−パーフルオ
ロヘプチル基、ｎ−パーフルオロオクチル基、ｎ−パー
フルオロノニル基、ｎ−パーフルオロデシル基、ｎ−パ
ーフルオロウンデシル基、ｎ−パーフルオロドデシル
基、ｎ−パーフルオロテトラデシル基、１−ヒドロパー
フルオロエチル基、１−ヒドロ−ｎ−パーフルオロプロ
ピル基、１−ヒドロ−ｎ−パーフルオロブチル基、１−
ヒドロ−ｎ−パーフルオロペンチル基、１−ヒドロ−ｎ
−パーフルオロヘキシル基、１−ヒドロ−ｎ−パーフル
オロヘプチル基、１−ヒドロ−ｎ−パーフルオロオクチ
ル基、１−ヒドロ−ｎ−パーフルオロノニル基、１−ヒ
ドロ−ｎ−パーフルオロデシル基、１−ヒドロ−ｎ−パ
ーフルオロウンデシル基、１−ヒドロ−ｎ−パーフルオ
ロドデシル基、１−ヒドロ−ｎ−パーフルオロテトラデ
シル基、2-fluoro-n-heptyl group, 4-fluoro-n-heptyl group, 5-fluoro-n-heptyl group, 2-fluoro-n-octyl group, 3-fluoro-n
-Octyl group, 6-fluoro-n-octyl group, 4-fluoro-n-nonyl group, 7-fluoro-n-nonyl group,
3-fluoro-n-decyl group, 6-fluoro-n-decyl group, 4-fluoro-n-dodecyl group, 8-fluoro-
n-dodecyl group, 5-fluoro-n-tetradecyl group,
9-fluoro-n-tetradecyl group, chloromethyl group,
Dichloromethyl group, trichloromethyl group, 2-chloroethyl group, 2,2-dichloroethyl group, 2,2,2-trichloroethyl group, 2,2,2,1-tetrachloroethyl group, 3-chloro-n-propyl Group, 2-chloro-n-butyl group, 4-chloro-n-butyl group, 2-chloro-n-
Pentyl group, 5-chloro-n-pentyl group, 5-chloro-n-hexyl group, 4-chloro-n-heptyl group, 6-
Chloro-n-octyl group, 7-chloro-n-nonyl group,
3-chloro-n-decyl group, 8-chloro-n-dodecyl group, perfluoroethyl group, n-perfluoropropyl group, n-perfluorobutyl group, n-perfluoropentyl group, n-perfluorohexyl group , N-perfluoroheptyl group, n-perfluorooctyl group, n-perfluorononyl group, n-perfluorodecyl group, n-perfluoroundecyl group, n-perfluorododecyl group, n-perfluorotetradecyl group Group, 1-hydroperfluoroethyl group, 1-hydro-n-perfluoropropyl group, 1-hydro-n-perfluorobutyl group, 1-
Hydro-n-perfluoropentyl group, 1-hydro-n
-Perfluorohexyl group, 1-hydro-n-perfluoroheptyl group, 1-hydro-n-perfluorooctyl group, 1-hydro-n-perfluorononyl group, 1-hydro-n-perfluorodecyl group, 1-hydro-n-perfluoroundecyl group, 1-hydro-n-perfluorododecyl group, 1-hydro-n-perfluorotetradecyl group,
【００２５】１，１−ジヒドロ−ｎ−パーフルオロプロ
ピル基、１，１−ジヒドロ−ｎ−パーフルオロブチル
基、１，１−ジヒドロ−ｎ−パーフルオロペンチル基、
１，１−ジヒドロ−３−ペンタフルオロエチルパーフル
オロペンチル基、１，１−ジヒドロ−ｎ−パーフルオロ
ヘキシル基、１，１−ジヒドロ−ｎ−パーフルオロヘプ
チル基、１，１−ジヒドロ−ｎ−パーフルオロオクチル
基、１，１−ジヒドロ−ｎ−パーフルオロノニル基、
１，１−ジヒドロ−ｎ−パーフルオロデシル基、１，１
−ジヒドロ−ｎ−パーフルオロウンデシル基、１，１−
ジヒドロ−ｎ−パーフルオロドデシル基、１，１−ジヒ
ドロ−ｎ−パーフルオロテトラデシル基、１，１−ジヒ
ドロ−ｎ−パーフルオロペンタデシル基、１，１−ジヒ
ドロ−ｎ−パーフルオロヘキサデシル基、１，１，３−
トリヒドロ−ｎ−パーフルオロプロピル基、１，１，３
−トリヒドロ−ｎ−パーフルオロブチル基、１，１，４
−トリヒドロ−ｎ−パーフルオロブチル基、１，１，４
−トリヒドロ−ｎ−パーフルオロペンチル基、１，１，
５−トリヒドロ−ｎ−パーフルオロペンチル基、１，
１，３−トリヒドロ−ｎ−パーフルオロヘキシル基、
１，１，６−トリヒドロ−ｎ−パーフルオロヘキシル
基、１，１，５−トリヒドロ−ｎ−パーフルオロヘプチ
ル基、１，１，７−トリヒドロ−ｎ−パーフルオロヘプ
チル基、１，１，８−トリヒドロ−ｎ−パーフルオロオ
クチル基、１，１，９−トリヒドロ−ｎ−パーフルオロ
ノニル基、１，１，１１−トリヒドロ−ｎ−パーフルオ
ロウンデシル基、２−（パーフルオロエチル）エチル
基、２−（ｎ−パーフルオロプロピル）エチル基、２−
（ｎ−パーフルオロブチル）エチル基、２−（ｎ−パー
フルオロペンチル）エチル基、２−（ｎ−パーフルオロ
ヘキシル）エチル基、２−（ｎ−パーフルオロヘプチ
ル）エチル基、２−（ｎ−パーフルオロオクチル）エチ
ル基、２−（ｎ−パーフルオロデシル）エチル基、２−
（ｎ−パーフルオロノニル）エチル基、２−（ｎ−パー
フルオロドデシル）エチル基、２−（パーフルオロ−
９’−メチルデシル）エチル基、２−トリフルオロメチ
ルプロピル基、３−（ｎ−パーフルオロプロピル）プロ
ピル基、３−（ｎ−パーフルオロブチル）プロピル基、
３−（ｎ−パーフルオロヘキシル）プロピル基、３−
（ｎ−パーフルオロヘプチル）プロピル基、３−（ｎ−
パーフルオロオクチル）プロピル基、３−（ｎ−パーフ
ルオロデシル）プロピル基、３−（ｎ−パーフルオロド
デシル）プロピル基、４−（パーフルオロエチル）ブチ
ル基、４−（ｎ−パーフルオロプロピル）ブチル基、４
−（ｎ−パーフルオロブチル）ブチル基、４−（ｎ−パ
ーフルオロペンチル）ブチル基、４−（ｎ−パーフルオ
ロヘキシル）ブチル基、４−（ｎ−パーフルオロヘプチ
ル）ブチル基、４−（ｎ−パーフルオロオクチル）ブチ
ル基、４−（ｎ−パーフルオロデシル）ブチル基、４−
（パーフルオロイソプロピル）ブチル基、1,1-dihydro-n-perfluoropropyl group, 1,1-dihydro-n-perfluorobutyl group, 1,1-dihydro-n-perfluoropentyl group,
1,1-dihydro-3-pentafluoroethylperfluoropentyl group, 1,1-dihydro-n-perfluorohexyl group, 1,1-dihydro-n-perfluoroheptyl group, 1,1-dihydro-n- Perfluorooctyl group, 1,1-dihydro-n-perfluorononyl group,
1,1-dihydro-n-perfluorodecyl group, 1,1
-Dihydro-n-perfluoroundecyl group, 1,1-
Dihydro-n-perfluorododecyl group, 1,1-dihydro-n-perfluorotetradecyl group, 1,1-dihydro-n-perfluoropentadecyl group, 1,1-dihydro-n-perfluorohexadecyl group , 1,1,3-
Trihydro-n-perfluoropropyl group, 1,1,3
-Trihydro-n-perfluorobutyl group, 1,1,4
-Trihydro-n-perfluorobutyl group, 1,1,4
-Trihydro-n-perfluoropentyl group, 1,1,
5-trihydro-n-perfluoropentyl group, 1,
1,3-trihydro-n-perfluorohexyl group,
1,1,6-trihydro-n-perfluorohexyl group, 1,1,5-trihydro-n-perfluoroheptyl group, 1,1,7-trihydro-n-perfluoroheptyl group, 1,1,8 -Trihydro-n-perfluorooctyl group, 1,1,9-trihydro-n-perfluorononyl group, 1,1,11-trihydro-n-perfluoroundecyl group, 2- (perfluoroethyl) ethyl group , 2- (n-perfluoropropyl) ethyl group, 2-
(N-perfluorobutyl) ethyl group, 2- (n-perfluoropentyl) ethyl group, 2- (n-perfluorohexyl) ethyl group, 2- (n-perfluoroheptyl) ethyl group, 2- (n -Perfluorooctyl) ethyl group, 2- (n-perfluorodecyl) ethyl group, 2-
(N-perfluorononyl) ethyl group, 2- (n-perfluorododecyl) ethyl group, 2- (perfluoro-)
9'-methyldecyl) ethyl group, 2-trifluoromethylpropyl group, 3- (n-perfluoropropyl) propyl group, 3- (n-perfluorobutyl) propyl group,
3- (n-perfluorohexyl) propyl group, 3-
(N-perfluoroheptyl) propyl group, 3- (n-
Perfluorooctyl) propyl group, 3- (n-perfluorodecyl) propyl group, 3- (n-perfluorododecyl) propyl group, 4- (perfluoroethyl) butyl group, 4- (n-perfluoropropyl) Butyl group, 4
-(N-perfluorobutyl) butyl group, 4- (n-perfluoropentyl) butyl group, 4- (n-perfluorohexyl) butyl group, 4- (n-perfluoroheptyl) butyl group, 4- ( n-perfluorooctyl) butyl group, 4- (n-perfluorodecyl) butyl group, 4-
(Perfluoroisopropyl) butyl group,
【００２６】５−（ｎ−パーフルオロプロピル）ペンチ
ル基、５−（ｎ−パーフルオロブチル）ペンチル基、５
−（ｎ−パーフルオロペンチル）ペンチル基、５−（ｎ
−パーフルオロヘキシル）ペンチル基、５−（ｎ−パー
フルオロヘプチル）ペンチル基、５−（ｎ−パーフルオ
ロオクチル）ペンチル基、６−（パーフルオロエチル）
ヘキシル基、６−（ｎ−パーフルオロプロピル）ヘキシ
ル基、６−（ｎ−パーフルオロブチル）ヘキシル基、６
−（ｎ−パーフルオロヘキシル）ヘキシル基、６−（ｎ
−パーフルオロヘプチル）ヘキシル基、６−（ｎ−パー
フルオロオクチル）ヘキシル基、６−（パーフルオロイ
ソプロピル）ヘキシル基、６−（パーフルオロ−７’−
メチルオクチル）ヘキシル基、７−（パーフルオロエチ
ル）ヘプチル基、７−（ｎ−パーフルオロプロピル）ヘ
プチル基、７−（ｎ−パーフルオロブチル）ヘプチル
基、７−（ｎ−パーフルオロペンチル）ヘプチル基、４
−フルオロシクロヘキシル基等のハロゲン原子で置換さ
れた直鎖、分岐鎖または環状のアルキル基を挙げること
ができるが、これらに限定されるものではない。5- (n-perfluoropropyl) pentyl group, 5- (n-perfluorobutyl) pentyl group, 5
-(N-perfluoropentyl) pentyl group, 5- (n
-Perfluorohexyl) pentyl group, 5- (n-perfluoroheptyl) pentyl group, 5- (n-perfluorooctyl) pentyl group, 6- (perfluoroethyl)
Hexyl group, 6- (n-perfluoropropyl) hexyl group, 6- (n-perfluorobutyl) hexyl group, 6
-(N-perfluorohexyl) hexyl group, 6- (n
-Perfluoroheptyl) hexyl group, 6- (n-perfluorooctyl) hexyl group, 6- (perfluoroisopropyl) hexyl group, 6- (perfluoro-7'-
Methyloctyl) hexyl group, 7- (perfluoroethyl) heptyl group, 7- (n-perfluoropropyl) heptyl group, 7- (n-perfluorobutyl) heptyl group, 7- (n-perfluoropentyl) heptyl group Base, 4
Examples thereof include, but are not limited to, a linear, branched or cyclic alkyl group substituted with a halogen atom such as a -fluorocyclohexyl group.
【００２７】Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5、Ｒ6、Ｒ7、
Ｒ8、Ｒ9およびＲ10のハロゲン原子の具体例としては、
例えば、フッ素原子、塩素原子、臭素原子などのハロゲ
ン原子を挙げることができる。R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 ,
Specific examples of the halogen atom of R 8 , R 9 and R 10 include
For example, a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom can be mentioned.
【００２８】本発明に係る一般式（１）で表されるアミ
ン化合物の具体例としては、例えば、以下に示す化合物
を挙げることができるが、本発明はこれらに限定される
ものではない。Specific examples of the amine compound represented by the general formula (1) according to the present invention include the compounds shown below, but the present invention is not limited thereto.
【００２９】１．Ｎ，Ｎ，Ｎ’，Ｎ’−テトラフェニル
−４−（６’−アミノナフタレン−２’−イル）アニリ
ン
２．Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（１”−ナフ
チル）―４−（６’−アミノナフタレン−２’−イル）
アニリン
３．Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（２”−ナフ
チル）４−（６’−アミノナフタレン−２’−イル）ア
ニリン
４．Ｎ，Ｎ’−ジフェニル−Ｎ、Ｎ’−ジ（３”−メチ
ルフェニル）―４−（６’−アミノナフタレン−２’−
イル）アニリン
５．Ｎ，Ｎ’−ジ（３”−メチルフェニル）−Ｎ，Ｎ’
−ジ（１”’−ナフチル）―４−（６’−アミノナフタ
レン−２’−イル）アニリン
６．Ｎ，Ｎ’−ジ（３”−メチルフェニル）−Ｎ，Ｎ’
−ジ（２”’−ナフチル）４−（６’−アミノナフタレ
ン−２’−イル）アニリン
７．Ｎ、Ｎ、Ｎ’，Ｎ’−テトラ（１”−ナフチル）―
４−（６’−アミノナフタレン−２’−イル）アニリン
８．Ｎ、Ｎ、Ｎ’，Ｎ’−テトラ（２”−ナフチル）−
４−（６’−アミノナフタレン−２’−イル）アニリン
９．Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（４”−フェ
ニルフェニル）−４−（６’−アミノナフタレン−２’
−イル）アニリン
１０．Ｎ，Ｎ’−ジ（１”−ナフチル）−Ｎ，Ｎ’−ジ
（４”’−フェニルフェニル）−４−（６’−アミノナ
フタレン−２’−イル）アニリン1. N, N, N ', N'-tetraphenyl-4- (6'-aminonaphthalen-2'-yl) aniline 2. N, N'-diphenyl-N, N'-di (1 "-naphthyl) -4- (6'-aminonaphthalen-2'-yl)
Aniline 3. N, N'-diphenyl-N, N'-di (2 "-naphthyl) 4- (6'-aminonaphthalene-2'-yl) aniline 4.N, N'-diphenyl-N, N'-di ( 3 "-methylphenyl) -4- (6'-aminonaphthalene-2'-
Il) aniline 5. N, N'-di (3 "-methylphenyl) -N, N '
-Di (1 "'-naphthyl) -4- (6'-aminonaphthalene-2'-yl) aniline 6.N, N'-di (3" -methylphenyl) -N, N'
-Di (2 "'-naphthyl) 4- (6'-aminonaphthalene-2'-yl) aniline 7.N, N, N', N'-tetra (1" -naphthyl)-
4- (6'-aminonaphthalene-2'-yl) aniline 8. N, N, N ', N'-tetra (2 "-naphthyl)-
4- (6'-aminonaphthalene-2'-yl) aniline 9. N, N'-diphenyl-N, N'-di (4 "-phenylphenyl) -4- (6'-aminonaphthalene-2 '
-Yl) aniline 10. N, N'-di (1 "-naphthyl) -N, N'-di (4"'-phenylphenyl) -4- (6'-aminonaphthalen-2'-yl) aniline
【００３０】１１．Ｎ，Ｎ’−ジ（２”−ナフチル）−
Ｎ，Ｎ’−ジ（４”’−フェニルフェニル）−４−
（６’−アミノナフタレン−２’−イル）アニリン
１２．Ｎ，Ｎ，Ｎ’，Ｎ’−テトラ（４”−フェニルフ
ェニル）−４−（６’−アミノナフタレン−２’−イ
ル）アニリン
１３．Ｎ，Ｎ，Ｎ’，Ｎ’−テトラ（３”−フェニルフ
ェニル）−４−（６’−アミノナフタレン−２’−イ
ル）アニリン
１４．Ｎ，Ｎ，Ｎ’，Ｎ’−テトラ（２”−フェニルフ
ェニル）−４−（６’−アミノナフタレン−２’−イ
ル）アニリン
１５．Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（４”−シ
クロヘキシルフェニル）−４−（６’−アミノナフタレ
ン−２’−イル）アニリン
１６．Ｎ，Ｎ’−ジフェニル−Ｎ−（１”−ナフチル）
−Ｎ’−（４”’−フェニルフェニル）−４−（６’−
アミノナフタレン−２’−イル）アニリン
１７．Ｎ，Ｎ’−ジフェニル−Ｎ−（１”−ナフチル）
−Ｎ’−（２”’−ナフチル）−４−（６’−アミノナ
フタレン−２’−イル）アニリン
１８．Ｎ，Ｎ’−ジフェニル−Ｎ−（１”−ナフチル）
−Ｎ’−（２”’−フェニルフェニル）−４−（６’−
アミノナフタレン−２’−イル）アニリン
１９．Ｎ，Ｎ’−ジ（１”−ナフチル）−Ｎ，Ｎ’−ジ
（４”’−シクロヘキシルフェニル）−４−（６’−ア
ミノナフタレン−２’−イル）アニリン
２０．Ｎ，Ｎ’−ジ（２”−ナフチル）−Ｎ，Ｎ’−ジ
（４”’−シクロヘキシルフェニル）−４−（６’−ア
ミノナフタレン−２’−イル）アニリン11. N, N'-di (2 "-naphthyl)-
N, N'-di (4 "'-phenylphenyl) -4-
(6'-Aminonaphthalen-2'-yl) aniline 12. N, N, N ', N'-tetra (4 "-phenylphenyl) -4- (6'-aminonaphthalen-2'-yl) aniline 13.N, N, N', N'-tetra (3" -Phenylphenyl) -4- (6'-aminonaphthalen-2'-yl) aniline 14. N, N, N ', N'-Tetra (2 "-phenylphenyl) -4- (6'-aminonaphthalene-2'-yl) aniline 15.N, N'-diphenyl-N, N'-di ( 4 "-cyclohexylphenyl) -4- (6'-aminonaphthalene-2'-yl) aniline 16. N, N'-diphenyl-N- (1 "-naphthyl)
-N '-(4 "'-phenylphenyl) -4- (6'-
Aminonaphthalene-2'-yl) aniline 17. N, N'-diphenyl-N- (1 "-naphthyl)
-N '-(2 "'-naphthyl) -4- (6'-aminonaphthalene-2'-yl) aniline 18.N, N'-diphenyl-N- (1" -naphthyl)
-N '-(2 "'-phenylphenyl) -4- (6'-
Aminonaphthalene-2'-yl) aniline 19. N, N'-di (1 "-naphthyl) -N, N'-di (4"'-cyclohexylphenyl) -4- (6'-aminonaphthalen-2'-yl) aniline 20. N, N'-di (2 "-naphthyl) -N, N'-di (4"'-cyclohexylphenyl) -4- (6'-aminonaphthalene-2'-yl) aniline
【００３１】２１．Ｎ，Ｎ’−ジ（４”−フェニルフェ
ニル）−Ｎ，Ｎ’−ジ（４”’−シクロヘキシルフェニ
ル）−４−（６’−アミノナフタレン−２’−イル）ア
ニリン
２２．Ｎ，Ｎ，Ｎ’，Ｎ’−テトラ（４”−シクロヘキ
シルフェニル）−４−（６’−アミノナフタレン−２’
−イル）アニリン
２３．Ｎ，Ｎ’−ジ（２”−メトキシフェニル）−Ｎ，
Ｎ’−ジ（１”’−ナフチル）−４−（６’−アミノナ
フタレン−２’−イル）アニリン
２４．Ｎ，Ｎ’−ジ（４”−フルオロフェニル）−Ｎ，
Ｎ’−ジ（１”’−ナフチル）−４−（６’−アミノナ
フタレン−２’−イル）アニリン
２５．Ｎ，Ｎ’−ジ（３”−メトキシフェニル）−Ｎ，
Ｎ’−ジ（１”’−ナフチル）−４−（６’−アミノナ
フタレン−２’−イル）アニリン
２６．Ｎ，Ｎ’−ジ（２”，６”−ジメチルフェニル）
−Ｎ，Ｎ’−ジ（１”’−ナフチル）−４−（６’−ア
ミノナフタレン−２’−イル）アニリン
２７．Ｎ，Ｎ’−ジ（４”−tert-ブチル−２”，６”
−ジメチルフェニル）−Ｎ，Ｎ’−ジ（４”’−フェニ
ルフェニル）−４−（６’−アミノナフタレン−２’−
イル）アニリン
２８．Ｎ，Ｎ’−ジ（３”，４”，５”−トリメチルフ
ェニル）−Ｎ，Ｎ’−ジフェニル− ４−（６’−アミ
ノナフタレン−２’−イル）アニリン
２９．Ｎ，Ｎ’−ジ（３”，４”，５”−トリメチルフ
ェニル）−Ｎ，Ｎ’−ジ（１”’−ナフチル）−４−
（６’−アミノナフタレン−２’−イル）アニリン21. N, N'-di (4 "-phenylphenyl) -N, N'-di (4"'-cyclohexylphenyl) -4- (6'-aminonaphthalen-2'-yl) aniline 22. N, N, N ', N'-tetra (4 "-cyclohexylphenyl) -4- (6'-aminonaphthalene-2'
-Yl) aniline 23. N, N'-di (2 "-methoxyphenyl) -N,
N'-di (1 "'-naphthyl) -4- (6'-aminonaphthalene-2'-yl) aniline 24.N, N'-di (4" -fluorophenyl) -N,
N'-di (1 "'-naphthyl) -4- (6'-aminonaphthalene-2'-yl) aniline 25.N, N'-di (3" -methoxyphenyl) -N,
N'-di (1 "'-naphthyl) -4- (6'-aminonaphthalene-2'-yl) aniline 26.N, N'-di (2", 6 "-dimethylphenyl)
-N, N'-di (1 "'-naphthyl) -4- (6'-aminonaphthalene-2'-yl) aniline 27.N, N'-di (4" -tert-butyl-2 ", 6 ”
-Dimethylphenyl) -N, N'-di (4 "'-phenylphenyl) -4- (6'-aminonaphthalene-2'-
Il) aniline 28. N, N'-di (3 ", 4", 5 "-trimethylphenyl) -N, N'-diphenyl-4- (6'-aminonaphthalen-2'-yl) aniline 29.N, N'-di (3 ", 4", 5 "-trimethylphenyl) -N, N'-di (1"'-naphthyl) -4-
(6'-Aminonaphthalene-2'-yl) aniline
【００３２】３０．Ｎ，Ｎ’−ジ（３”−シクロヘキシ
ルフェニル）−Ｎ，Ｎ’−ジ（４”’−フェニルフェニ
ル）−４−（６’−アミノナフタレン−２’−イル）ア
ニリン
３１．Ｎ，Ｎ’−ジ（２”−sec−ブチルフェニル）−
Ｎ，Ｎ’−ジ（１”’−ナフチル）−４−（６’−アミ
ノナフタレン−２’−イル）アニリン
３２．Ｎ，Ｎ’−ジ（２”，３”，６”−トリメチルフ
ェニル）−Ｎ，Ｎ’−ジ（４”’−シクロヘキシルフェ
ニル）−４−（６’−アミノナフタレン−２’−イル）
アニリン
３３．Ｎ，Ｎ’−ジ（３”−メトキシフェニル）−Ｎ，
Ｎ’−ジ（４”’−tert−ブチル−２”’，６”’−ジ
メチルフェニル）−４−（６’−アミノナフタレン−
２’−イル）アニリン
３４．Ｎ，Ｎ’−ジ（２”，３”−ジフルオロフェニ
ル）−Ｎ，Ｎ’−ジ（１”’−ナフチル）−４−（６’
−アミノナフタレン−２’−イル）アニリン
３５．Ｎ，Ｎ’−ジ（３”−クロロフェニル）−Ｎ，
Ｎ’−ジ（３”’−シクロヘキシルフェニル）−４−
（６’−アミノナフタレン−２’−イル）アニリン
３６．Ｎ，Ｎ，Ｎ’−テトラフェニル−Ｎ’−（１’−
ナフチル）−４−（６’−アミノナフタレン−２’−イ
ル）アニリン
３７．Ｎ−（１”−ピレニル）−Ｎ，Ｎ’，Ｎ’−トリ
フェニル−４−（６’−アミノナフタレン−２’−イ
ル）アニリン
３８．Ｎ−（１”−ナフチル）−Ｎ，Ｎ’，Ｎ’−トリ
フェニル−４−（６’−アミノナフタレン−２’−イ
ル）アニリン
３９．Ｎ−（２”−ナフチル）−Ｎ，Ｎ’，Ｎ’−トリ
フェニル−４−（６’−アミノナフタレン−２’−イ
ル）アニリン30. N, N'-di (3 "-cyclohexylphenyl) -N, N'-di (4"'-phenylphenyl) -4- (6'-aminonaphthalen-2'-yl) aniline 31. N, N'-di (2 "-sec-butylphenyl)-
N, N'-di (1 "'-naphthyl) -4- (6'-aminonaphthalene-2'-yl) aniline 32.N, N'-di (2", 3 ", 6" -trimethylphenyl) -N, N'-di (4 "'-cyclohexylphenyl) -4- (6'-aminonaphthalen-2'-yl)
Aniline 33. N, N'-di (3 "-methoxyphenyl) -N,
N'-di (4 "'-tert-butyl-2"', 6 "'-dimethylphenyl) -4- (6'-aminonaphthalene-
2'-yl) aniline 34. N, N'-di (2 ", 3" -difluorophenyl) -N, N'-di (1 "'-naphthyl) -4- (6'
-Aminonaphthalene-2'-yl) aniline 35. N, N'-di (3 "-chlorophenyl) -N,
N'-di (3 "'-cyclohexylphenyl) -4-
(6'-Aminonaphthalen-2'-yl) aniline 36. N, N, N'-tetraphenyl-N '-(1'-
Naphthyl) -4- (6'-aminonaphthalene-2'-yl) aniline 37. N- (1 "-pyrenyl) -N, N ', N'-triphenyl-4- (6'-aminonaphthalen-2'-yl) aniline 38.N- (1" -naphthyl) -N, N' , N'-triphenyl-4- (6'-aminonaphthalene-2'-yl) aniline 39. N- (2 "-naphthyl) -N, N ', N'-triphenyl-4- (6'-aminonaphthalene-2'-yl) aniline
【００３３】４０．Ｎ−（４”−フェニルフェニル）−
Ｎ，Ｎ’，Ｎ’−トリフェニル−４−（６’−アミノナ
フタレン−２’−イル）アニリン
４１．Ｎ−（３”−シクロヘキシルフェニル）−Ｎ，
Ｎ’，Ｎ’−トリフェニル−４−（６’−アミノナフタ
レン−２’−イル）アニリン
４２．Ｎ，Ｎ’−ジフェニル−Ｎ−（１”−ピレニル）
−Ｎ’−（２”’−ナフチル）−４−（６’−アミノナ
フタレン−２’−イル）アニリン
４３．Ｎ，Ｎ’−ジフェニル−Ｎ−（１”−ピレニル）
−Ｎ’−（４”’−フェニルフェニル）−４−（６’−
アミノナフタレン−２’−イル）アニリン
４４．Ｎ，Ｎ，Ｎ’−トリフェニル−Ｎ’−（４”−フ
ェニルフェニル）−４−（６’−アミノナフタレン−
２’−イル）アニリン
４５．Ｎ，Ｎ−ジフェニル−Ｎ’，Ｎ’−ジ（１”−ナ
フチル）―３−フルオロ−４−（６’−アミノナフタレ
ン−２’−イル）アニリン
４６．Ｎ，Ｎ−ジフェニル−Ｎ’，Ｎ’−ジ（４”−フ
ェニルフェニル）−２−フルオロ−４−（６’−アミノ
ナフタレン−２’−イル）アニリン
４７．Ｎ，Ｎ，Ｎ’−トリフェニル−Ｎ’−（１”−ナ
フチル）−２−メチル−４−（６’−アミノナフタレン
−２’−イル）アニリン
４８．Ｎ，Ｎ，Ｎ’−トリフェニル−Ｎ’−（２”−ナ
フチル）−２，５−ジメチル−４−（６’−アミノナフ
タレン−２’−イル）−アニリン
４９．Ｎ，Ｎ，Ｎ’−トリフェニル−Ｎ’−（４”−フ
ェニルフェニル）−２−メチル−４−（６’−アミノナ
フタレン−２’−イル）アニリン40. N- (4 "-phenylphenyl)-
N, N ', N'-triphenyl-4- (6'-aminonaphthalen-2'-yl) aniline 41. N- (3 "-cyclohexylphenyl) -N,
N ', N'-triphenyl-4- (6'-aminonaphthalene-2'-yl) aniline 42. N, N'-diphenyl-N- (1 "-pyrenyl)
-N '-(2 "'-naphthyl) -4- (6'-aminonaphthalene-2'-yl) aniline 43.N, N'-diphenyl-N- (1" -pyrenyl)
-N '-(4 "'-phenylphenyl) -4- (6'-
Aminonaphthalene-2'-yl) aniline 44. N, N, N'-triphenyl-N '-(4 "-phenylphenyl) -4- (6'-aminonaphthalene-
2'-yl) aniline 45. N, N-diphenyl-N ', N'-di (1 "-naphthyl) -3-fluoro-4- (6'-aminonaphthalene-2'-yl) aniline 46.N, N-diphenyl-N', N'-di (4 "-phenylphenyl) -2-fluoro-4- (6'-aminonaphthalen-2'-yl) aniline 47. N, N, N'-triphenyl-N '-(1 "-naphthyl) -2-methyl-4- (6'-aminonaphthalen-2'-yl) aniline 48.N, N, N'-triphenyl -N '-(2 "-naphthyl) -2,5-dimethyl-4- (6'-aminonaphthalen-2'-yl) -aniline 49. N, N, N'-triphenyl-N '-(4 "-phenylphenyl) -2-methyl-4- (6'-aminonaphthalen-2'-yl) aniline
【００３４】５０．Ｎ，Ｎ，Ｎ’−トリ（３”−メチル
フェニル）−Ｎ’−（４”’−フルオロフェニル）−２
−クロロ−４−（６’−アミノナフタレン−２’−イ
ル）アニリン
５１．Ｎ，Ｎ，Ｎ’−トリ（４”−メチルフェニル）−
Ｎ’−フェニル−２−メトキシ−４−（６’−アミノナ
フタレン−２’−イル）アニリン
５２．Ｎ−（９”−フェナントレニル）−Ｎ，Ｎ’，
Ｎ’−トリフェニル−２−メトキシ−４−（６’−アミ
ノナフタレン−２’−イル）アニリン
５３．Ｎ−（１”−ピレニル）−Ｎ，Ｎ’，Ｎ’−トリ
フェニル−２−メチル−４−（６’−アミノナフタレン
−２’−イル）アニリン
５４．Ｎ，Ｎ，Ｎ’，Ｎ’−テトラフェニル−３−イソ
プロピル−４−（１’−メチル−６’−アミノナフタレ
ン−２’−イル）アニリン
５５．Ｎ，Ｎ，Ｎ’−トリフェニル−Ｎ’−（１”−ナ
フチル）−３−メチル−４−（１’−フルオロ−６’−
アミノナフタレン−２’−イル）アニリン
５６．Ｎ，Ｎ−ジ（３”−メチルフェニル）−Ｎ’，
Ｎ’−ジフェニル−４−（１’−メチル−６’−アミノ
ナフタレン−２’−イル）アニリン
５７．Ｎ，Ｎ−ジ（４”−シクロヘキシルフェニル）−
Ｎ’，Ｎ’−ジフェニル−４−（１’−メチル−６’−
アミノナフタレン−２’−イル）アニリン
５８．Ｎ，Ｎ−ジ（３”−メチルフェニル）−Ｎ’，
Ｎ’−ジフェニル −４−（６’−アミノナフタレン−
２’−イル）アニリン
５９．Ｎ，Ｎ−ジ（１”−ナフチル）−Ｎ’，Ｎ’−ジ
フェニル −４−（６’−アミノナフタレン−２’−イ
ル）アニリン50. N, N, N'-tri (3 "-methylphenyl) -N '-(4"'-fluorophenyl) -2
-Chloro-4- (6'-aminonaphthalene-2'-yl) aniline 51. N, N, N'-tri (4 "-methylphenyl)-
N'-phenyl-2-methoxy-4- (6'-aminonaphthalene-2'-yl) aniline 52. N- (9 "-phenanthrenyl) -N, N ',
N'-triphenyl-2-methoxy-4- (6'-aminonaphthalene-2'-yl) aniline 53. N- (1 "-pyrenyl) -N, N ', N'-triphenyl-2-methyl-4- (6'-aminonaphthalen-2'-yl) aniline 54.N, N, N', N ' -Tetraphenyl-3-isopropyl-4- (1'-methyl-6'-aminonaphthalene-2'-yl) aniline 55.N, N, N'-triphenyl-N '-(1 "-naphthyl)- 3-methyl-4- (1'-fluoro-6'-
Aminonaphthalene-2'-yl) aniline 56. N, N-di (3 "-methylphenyl) -N ',
N'-diphenyl-4- (1'-methyl-6'-aminonaphthalene-2'-yl) aniline 57. N, N-di (4 "-cyclohexylphenyl)-
N ', N'-diphenyl-4- (1'-methyl-6'-
Aminonaphthalene-2'-yl) aniline 58. N, N-di (3 "-methylphenyl) -N ',
N'-diphenyl-4- (6'-aminonaphthalene-
2'-yl) aniline 59. N, N-di (1 "-naphthyl) -N ', N'-diphenyl-4- (6'-aminonaphthalene-2'-yl) aniline
【００３５】６０．Ｎ，Ｎ−ジ（４”−フェニルフェニ
ル）−Ｎ’，Ｎ’−ジフェニル −４−（６’−アミノ
ナフタレン−２’−イル）アニリン
６１．Ｎ，Ｎ，Ｎ’，Ｎ’−テトラフェニル−３−フェ
ニル−４−（６’−アミノナフタレン−２’−イル）ア
ニリン
６２．Ｎ，Ｎ，Ｎ’，Ｎ’−テトラフェニル−２−フェ
ニル−４−（６’−アミ
ノナフタレン−２’−イル）アニリン６３．Ｎ，Ｎ，
Ｎ’，Ｎ’−テトラフェニル−４−（５’−フェニル−
６’−アミノナフタレン−２’−イル）アニリン
６４．Ｎ−（１”−ナフチル）−Ｎ，Ｎ’，Ｎ’−トリ
フェニル−２−フェニル−４−（６’−アミノナフタレ
ン−２’−イル）アニリン
６５．Ｎ−（２”−ナフチル）−Ｎ，Ｎ’，Ｎ’−トリ
フェニル−３−フェニルオキシ−４−（６’−アミノナ
フタレン−２’−イル）アニリン
６６．Ｎ，Ｎ−ジ（１”−ナフチル）−Ｎ’，Ｎ’−ジ
フェニル−３−フェニル−４−（６’−アミノナフタレ
ン−２’−イル）アニリン60. N, N-di (4 "-phenylphenyl) -N ', N'-diphenyl-4- (6'-aminonaphthalene-2'-yl) aniline 61.N, N, N', N'-tetraphenyl -3-Phenyl-4- (6'-aminonaphthalene-2'-yl) aniline 62. N, N, N ', N'-tetraphenyl-2-phenyl-4- (6'-aminonaphthalene-2' -Yl) aniline 63.N, N,
N ', N'-tetraphenyl-4- (5'-phenyl-
6'-aminonaphthalene-2'-yl) aniline 64. N- (1 "-naphthyl) -N, N ', N'-triphenyl-2-phenyl-4- (6'-aminonaphthalen-2'-yl) aniline 65. N- (2" -naphthyl)- N, N ', N'-triphenyl-3-phenyloxy-4- (6'-aminonaphthalen-2'-yl) aniline 66. N, N-di (1 "-naphthyl) -N ', N'-diphenyl-3-phenyl-4- (6'-aminonaphthalen-2'-yl) aniline
【００３６】本発明の一般式（１）で表されるアミン化
合物は其自体公知の方法により製造することができる。The amine compound represented by the general formula (1) of the present invention can be produced by a method known per se.
【００３７】一般式（１）で表されるアミン化合物の製
造（化４）Production of amine compound represented by the general formula (1)
【００３８】[0038]
【化４】
（式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5、Ｒ6、Ｒ7、Ｒ8、Ｒ
9およびＲ10Ａｒ1、Ａｒ 2、Ａｒ3およびＡｒ4は前述の
意味を表し、Ｘは塩素、臭素、ヨウ素等のハロゲン原子
を表す）[Chemical 4]
(In the formula, R1, R2, R3, RFour, RFive, R6, R7, R8, R
9And RTenAr1, Ar 2, Ar3And ArFourIs the above
X means a halogen atom such as chlorine, bromine or iodine
Represents)
【００３９】すなわち、一般式（２）で表されるハロゲ
ン化アニリン誘導体に、一般式（３）で表されるナフチ
ルボロン酸誘導体を、パラジウム触媒（例えば、テトラ
キストリフェニルホスフィンパラジウム）および塩基
（例えば、トリエチルアミン、ピリジン等の有機塩基、
炭酸ナトリウム、炭酸カリウム等の無機塩基）の存在下
に反応させることにより製造することができる。That is, a naphthylboronic acid derivative represented by the general formula (3) is added to a halogenated aniline derivative represented by the general formula (2), a palladium catalyst (eg tetrakistriphenylphosphine palladium) and a base (eg the tetrakistriphenylphosphine palladium). , Organic bases such as triethylamine, pyridine,
It can be produced by reacting in the presence of an inorganic base such as sodium carbonate or potassium carbonate.
【００４０】尚、一般式（２）で表されるハロゲン化ア
ニリン誘導体は、例えば、以下に示す工程（化５）に従
い製造することができる。The halogenated aniline derivative represented by the general formula (2) can be produced, for example, according to the following process (Formula 5).
【００４１】[0041]
【化５】
（式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5およびＲ6、Ａｒ1お
よびＡｒ2、Ｘは前述の意味を表し、Ｌはトリフルオロ
メタンスルホニルオキシ基、ｐ−トルエンスルホニルオ
キシ基、ハロゲン原子等の脱離基を表し、Ｘ’はヨウ
素、臭素等のハロゲン原子を表す）[Chemical 5] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 , Ar 1 and Ar 2 , X represent the above-mentioned meanings, L represents a trifluoromethanesulfonyloxy group, and p-toluenesulfonyloxy group. , Represents a leaving group such as a halogen atom, and X ′ represents a halogen atom such as iodine or bromine)
【００４２】すなわち、一般式（４）で表されるハロゲ
ン化ベンゼン化合物にＡｒ1−ＮＨ2を作用させて、一般
式（５）で表される化合物とし、その後、Ａｒ2−Ｘ’
を作用させて、一般式（２）で表されるハロゲン化アニ
リン誘導体を製造することができる。That is, Ar 1 -NH 2 is allowed to act on the halogenated benzene compound represented by the general formula (4) to obtain the compound represented by the general formula (5), and then Ar 2 -X '.
Can be reacted to produce a halogenated aniline derivative represented by the general formula (2).
【００４３】尚、一般式（４）で表されるハロゲン化ベ
ンゼン化合物とＡｒ1−ＮＨ2の反応は、一般式（４）で
表されるハロゲン化ベンゼン化合物と、Ａｒ1−ＮＨ2を
銅触媒またはパラジウム触媒、および塩基の存在下に反
応させる方法により製造することができる。The reaction between the halogenated benzene compound represented by the general formula (4) and Ar 1 -NH 2 is carried out by converting the halogenated benzene compound represented by the general formula (4) and Ar 1 -NH 2 into copper. It can be produced by a method of reacting in the presence of a catalyst or a palladium catalyst and a base.
【００４４】また、一般式（５）で表されるナフチルボ
ロン酸誘導体は、例えば、以下に示す工程（化６）に従
い製造することができる。The naphthylboronic acid derivative represented by the general formula (5) can be produced, for example, according to the following process (Chemical formula 6).
【００４５】[0045]
【化６】
（式中、Ｒ7、Ｒ8、Ｒ9、Ｒ10、Ｒ11およびＲ12、Ａｒ3
およびＡｒ4、Ｘは前述の意味を表す）[Chemical 6] (In the formula, R 7 , R 8 , R 9 , R 10 , R 11 and R 12 , Ar 3
And Ar 4 and X have the above-mentioned meanings)
【００４６】すなわち、一般式（６）で表されるハロ
ゲン化ナフチルアミン誘導体に、マグネシウムを作用さ
せ、グリニャール試薬を調整した後、ホウ酸トリメチル
と反応させ、その後、酸で処理する方法、または一般
式（６）で表されるハロゲン化ナフチルアミン誘導体
に、ｎ−ブチルリチウムを作用させ、リチオ化し、その
後、ホウ酸トリイソプロピルを作用させ、その後、酸で
処理する方法等により製造することができる。That is, magnesium is allowed to act on the halogenated naphthylamine derivative represented by the general formula (6) to prepare a Grignard reagent, which is then reacted with trimethyl borate and then treated with an acid, or the general formula The halogenated naphthylamine derivative represented by (6) can be produced by a method in which n-butyllithium is allowed to act, lithiate, then triisopropyl borate is allowed to act, and then treated with an acid.
【００４７】また、一般式（１）で表されるアミン化合
物は別法として、以下に示す工程（化７）によっても製
造することが可能である。Alternatively, the amine compound represented by the general formula (1) can be produced by the following process (chemical formula 7) as an alternative method.
【００４８】[0048]
【化７】
（式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5、Ｒ6、Ｒ7、Ｒ8、Ｒ
9およびＲ10、Ａｒ1、Ａｒ2、Ａｒ3およびＡｒ4、
Ｘ’、Ｌは前述の意味を表す）[Chemical 7] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R
9 and R 10 , Ar 1 , Ar 2 , Ar 3 and Ar 4 ,
X'and L represent the above meanings)
【００４９】すなわち、一般式（７）で表される化合物
にＡｒ1−ＮＨ2および／またはＡｒ 3−ＮＨ2を作用させ
て、一般式（８）で表される化合物を製造し、その後、
Ａｒ 2−Ｘ’および／またはＡｒ4−Ｘ’を作用させて、
一般式（１）で表される化合物を製造することができ
る。That is, the compound represented by the general formula (7)
To Ar1-NH2And / or Ar 3-NH2To act
To produce a compound represented by the general formula (8), and
Ar 2-X 'and / or ArFour-Acting X ',
A compound represented by the general formula (1) can be produced
It
【００５０】次に本発明の有機電界発光素子ついて説明
する。本発明の有機電界発光素子は、一対の電極間に、
一般式（１）で表されるアミン化合物を少なくとも１種
含有する層を少なくとも一層挟持してなるものである。
有機電界発光素子は、通常一対の電極間に少なくとも１
種の発光成分を含有する発光層を少なくとも一層挟持し
てなるものである。発光層に使用する化合物の正孔注入
および正孔輸送、電子注入および電子輸送の各機能レベ
ルを考慮し、所望に応じて、正孔注入成分を含有する正
孔注入輸送層および／または電子注入輸送成分を含有す
る電子注入輸送層を設けることもできる。Next, the organic electroluminescent device of the present invention will be described. The organic electroluminescent element of the present invention, between a pair of electrodes,
At least one layer containing at least one amine compound represented by the general formula (1) is sandwiched.
An organic electroluminescent device usually has at least one electrode between a pair of electrodes.
At least one light emitting layer containing two kinds of light emitting components is sandwiched. Considering the respective functional levels of hole injection and hole transport, electron injection and electron transport of the compound used for the light emitting layer, and if desired, a hole injection transport layer and / or electron injection containing a hole injection component. An electron injecting and transporting layer containing a transporting component can also be provided.
【００５１】例えば、発光層に使用する化合物の正孔注
入機能、正孔輸送機能および／または電子注入機能、電
子輸送機能が良好な場合には、発光層が正孔注入輸送層
および／または電子注入輸送層を兼ねた型の素子構成と
して一層型の素子構成とすることができる。また、発光
層が正孔注入機能および／または正孔輸送機能に乏しい
場合には発光層の陽極側に正孔注入輸送層を設けた二層
型の素子構成、発光層が電子注入機能および／または電
子輸送機能に乏しい場合には発光層の陰極側に電子注入
輸送層を設けた二層型の素子構成とすることができる。
さらには発光層を正孔注入輸送層と電子注入輸送層で挟
み込んだ構成の三層型の素子構成とすることも可能であ
る。For example, when the compound used in the light emitting layer has a good hole injecting function, hole transporting function and / or electron injecting function, or electron transporting function, the light emitting layer is a hole injecting and transporting layer and / or an electron. A single-layer element structure can be used as the element structure that also serves as the injection and transport layer. When the light emitting layer has a poor hole injecting function and / or hole transporting function, a two-layer type element structure in which a hole injecting and transporting layer is provided on the anode side of the light emitting layer, and the light emitting layer has an electron injecting function and / or Alternatively, when the electron transporting function is poor, a two-layer element structure can be used in which an electron injecting and transporting layer is provided on the cathode side of the light emitting layer.
Further, it is also possible to form a three-layer type device structure in which the light emitting layer is sandwiched between the hole injecting and transporting layer and the electron injecting and transporting layer.
【００５２】また、正孔注入輸送層、電子注入輸送層お
よび発光層のそれぞれの層は、一層構造であっても多層
構造であってもよく、正孔注入輸送層および電子注入輸
送層は、それぞれの層において、注入機能を有する層と
輸送機能を有する層を別々に設けて構成することもでき
る。Each of the hole injecting and transporting layer, the electron injecting and transporting layer and the light emitting layer may have a single layer structure or a multi layer structure. The hole injecting and transporting layer and the electron injecting and transporting layer are In each layer, a layer having an injection function and a layer having a transport function may be separately provided.
【００５３】本発明の有機電界発光素子において、一般
式（１）で表されるアミン化合物で表されるアミン化合
物は、正孔注入輸送層および／または発光層の構成成分
として使用することが好ましく、正孔注入輸送層の構成
成分として使用することがより好ましい。In the organic electroluminescent device of the present invention, the amine compound represented by the amine compound represented by the general formula (1) is preferably used as a constituent component of the hole injecting and transporting layer and / or the light emitting layer. More preferably, it is used as a constituent of the hole injecting and transporting layer.
【００５４】本発明の有機電界発光素子において、一般
式（１）で表されるアミン化合物で表されるアミン化合
物は、単独で使用してもよく、また複数併用してもよ
い。In the organic electroluminescence device of the present invention, the amine compound represented by the amine compound represented by the general formula (1) may be used alone or in combination.
【００５５】本発明の有機電界発光素子の構成として
は、特に限定されるものではないが、例えば、（Ａ）陽
極／正孔注入輸送層／発光層／電子注入輸送層／陰極型
素子（図１）、（Ｂ）陽極／正孔注入輸送層／発光層／
陰極型素子（図２）、（Ｃ）陽極／発光層／電子注入輸
送層／陰極型素子（図３）、（Ｄ）陽極／発光層／陰極
型素子（図４）、などを挙げることができる。さらに
は、発光層を電子注入輸送層で挟み込んだ形の（Ｅ）陽
極／正孔注入輸送層／電子注入輸送層／発光層／電子注
入輸送層／陰極型素子（図５）とすることもできる。ま
た、（Ｄ）の型の素子構成としては、発光層として発光
成分を一層形態で一対の電極間に挟持させた型の素子、
（Ｆ）発光層として正孔注入輸送成分、発光成分および
電子注入成分を混合させた一層形態で一対の電極間に挟
持させた型の素子（図６）、（Ｇ）発光層として正孔注
入輸送成分および発光成分を混合させた一層形態で一対
の電極間に挟持させた型の素子（図７）、（Ｈ）発光層
として発光成分および電子注入成分を混合させた一層形
態で一対の電極間に挟持させた型の素子（図８）のいず
れであってもよい。The constitution of the organic electroluminescent device of the present invention is not particularly limited, but for example, (A) anode / hole injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type device (see FIG. 1), (B) anode / hole injecting / transporting layer / light emitting layer /
Examples include a cathode type device (FIG. 2), (C) anode / light emitting layer / electron injecting / transporting layer / cathode type device (FIG. 3), (D) anode / light emitting layer / cathode type device (FIG. 4), and the like. it can. Further, (E) anode / hole injecting / transporting layer / electron injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element (FIG. 5) in which the light emitting layer is sandwiched between electron injecting and transporting layers may be used. it can. The (D) type element structure is a type element in which a light emitting component is sandwiched between a pair of electrodes in a single layer as a light emitting layer,
(F) A device of a type in which a hole injection / transport component, a light emitting component and an electron injection component are mixed as a light emitting layer and sandwiched between a pair of electrodes (FIG. 6), and (G) a hole injection is performed as a light emitting layer. An element of a type in which a transport component and a light emitting component are mixed and sandwiched between a pair of electrodes (FIG. 7), and (H) a pair of electrodes in a single layer in which a light emitting component and an electron injection component are mixed as a light emitting layer. It may be any of the types of elements sandwiched between them (FIG. 8).
【００５６】本発明の有機電界発光素子は、これらの素
子構成に限定されるものではなく、それぞれの型の素子
において、正孔注入輸送層、発光層、電子注入輸送層を
複数設けることも可能である。また、それぞれの型の素
子において、正孔注入輸送層を発光層との間に、正孔注
入輸送成分と発光成分の混合層および／または発光層と
電子注入輸送層との間に、発光成分と電子注入輸送成分
の混合層を設けることもできる。The organic electroluminescent device of the present invention is not limited to these device configurations, and a plurality of hole injecting and transporting layers, light emitting layers and electron injecting and transporting layers may be provided in each type of device. Is. Further, in each type of device, the hole injecting and transporting layer is provided between the light emitting layer, the mixed layer of the hole injecting and transporting component and the light emitting component and / or the light emitting component is provided between the light emitting layer and the electron injecting and transporting layer. It is also possible to provide a mixed layer of the electron injecting and transporting component.
【００５７】好ましい有機電界発光素子の構成は、
（Ａ）型素子、（Ｂ）型素子、（Ｅ）型素子、（Ｆ）型
素子または（Ｇ）型素子であり、より好ましくは、
（Ａ）型素子、（Ｂ）型素子または（Ｇ）型素子であ
る。A preferred organic electroluminescent device has the following structure:
(A) type element, (B) type element, (E) type element, (F) type element or (G) type element, and more preferably,
It is an (A) type element, a (B) type element or a (G) type element.
【００５８】以下、本発明の有機電界発光素子の構成要
素に関し、詳細に説明する。なお、例として（図１）に
示す（Ａ）陽極／正孔注入輸送層／発光層／電子注入輸
送層／陰極型素子を取り上げて説明する。The constituent elements of the organic electroluminescent device of the present invention will be described in detail below. As an example, (A) anode / hole injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element shown in FIG. 1 will be described.
【００５９】（図１）において、１は基板、２は陽極、
３は正孔注入輸送層、４は発光層、５は電子注入輸送
層、６は陰極、７は電源を示す。本発明の有機電界発光
素子は基板１に支持されていることが好ましく、基板と
しては、特に限定されるものではないが、透明ないし半
透明である基板が好ましく、材質としては、ソーダライ
ムガラス、ボロシリケートガラス等のガラスおよびポリ
エステル、ポリカーボネート、、ポリスルホン、ポリエ
ーテルスルホン、ポリアクリレート、ポリメチルメタク
リレート、ポリプロピレン、ポリエチレン等の透明性高
分子が挙げられる。また、半透明プラスチックシート、
石英、透明セラミックスあるいはこれらを組み合わせた
複合シートからなる基板を使用することもできる。さら
に、基板に、例えば、カラーフィルター膜、色変換膜、
誘電体反射膜を組み合わせて、発光色をコントロールす
ることもできる。In FIG. 1, 1 is a substrate, 2 is an anode,
3 is a hole injecting and transporting layer, 4 is a light emitting layer, 5 is an electron injecting and transporting layer, 6 is a cathode, and 7 is a power source. The organic electroluminescent element of the present invention is preferably supported on the substrate 1. The substrate is not particularly limited, but a transparent or semitransparent substrate is preferable, and the material is soda lime glass, Examples thereof include glass such as borosilicate glass and transparent polymers such as polyester, polycarbonate, polysulfone, polyether sulfone, polyacrylate, polymethylmethacrylate, polypropylene and polyethylene. Also, semi-transparent plastic sheet,
It is also possible to use a substrate made of quartz, transparent ceramics, or a composite sheet in which these are combined. Further, on the substrate, for example, a color filter film, a color conversion film,
It is also possible to control the emission color by combining a dielectric reflection film.
【００６０】陽極２としては、仕事関数の比較的大きい
金属、合金または導電性化合物を電極材料として使用す
ることが好ましい。陽極に使用する電極材料としては、
例えば、金、白金、銀、銅、コバルト、ニッケル、パラ
ジウム、バナジウム、タングステン、酸化インジウム
（Ｉｎ2Ｏ3）、酸化錫（ＳｎＯ2）、酸化亜鉛、ＩＴＯ
（インジウム・チン・オキサイド：Ｉｎｄｉｕｍ Ｔｉ
ｎ Ｏｘｉｄｅ）、ポリチオフェン、ポリピロールなど
を挙げることができる。これらの電極材料は単独で使用
してもよく、あるいは複数併用してもよい。As the anode 2, it is preferable to use a metal, an alloy or a conductive compound having a relatively large work function as an electrode material. As the electrode material used for the anode,
For example, gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, indium oxide (In 2 O 3 ), tin oxide (SnO 2 ), zinc oxide, ITO.
(Indium-Tin-Oxide: Indium Ti
n Oxide), polythiophene, polypyrrole and the like. These electrode materials may be used alone or in combination.
【００６１】陽極は、これらの電極材料を、例えば、蒸
着法、スパッタリング法等の方法により、基板の上に形
成することができる。また、陽極は一層構造であっても
よく、あるいは多層構造であってもよい。陽極のシート
電気抵抗は、好ましくは、数百Ω／□以下、より好まし
くは、５〜５０Ω／□程度に設定する。陽極の厚みは使
用する電極材料の材質にもよるが、一般に、５〜１００
０ｎｍ程度、より好ましくは、１０〜５００ｎｍ程度に
設定する。The anode can be formed of these electrode materials on the substrate by a method such as a vapor deposition method or a sputtering method. The anode may have a single layer structure or a multilayer structure. The sheet electric resistance of the anode is preferably set to several hundreds Ω / □ or less, more preferably about 5 to 50Ω / □. Although the thickness of the anode depends on the material of the electrode material used, it is generally 5 to 100.
The thickness is set to about 0 nm, more preferably about 10 to 500 nm.
【００６２】正孔注入輸送層３は、陽極からの正孔（ホ
ール）の注入を容易にする機能、および注入された正孔
を輸送する機能を有する化合物を含有する層である。本
発明の電界発光素子の正孔注入輸送層は、一般式（１）
で表される化合物および／または他の正孔注入輸送機能
を有する化合物（例えば、フタロシアニン誘導体、トリ
アリールアミン誘導体、トリアリールメタン誘導体、オ
キサゾール誘導体、ヒドラゾン誘導体、スチルベン誘導
体、ピラゾリン誘導体、ポリシラン誘導体、ポリフェニ
レンビニレンおよびその誘導体、ポリチオフェンおよび
その誘導体、ポリ−Ｎ−ビニルカルバゾールなど）を少
なくとも1種使用して形成することができる。The hole injecting and transporting layer 3 is a layer containing a compound having a function of facilitating the injection of holes from the anode and a function of transporting the injected holes. The hole injecting and transporting layer of the electroluminescent device of the present invention has the general formula (1):
And / or other compounds having a hole injecting and transporting function (for example, phthalocyanine derivative, triarylamine derivative, triarylmethane derivative, oxazole derivative, hydrazone derivative, stilbene derivative, pyrazoline derivative, polysilane derivative, polyphenylene) Vinylene and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole, etc.) can be used to form the film.
【００６３】正孔注入輸送機能を有する化合物は、単独
で使用してもよく、または複数併用してもよい。The compounds having a hole injecting and transporting function may be used alone or in combination of two or more.
【００６４】本発明の有機電界発光素子は、好ましく
は、正孔注入輸送層に一般式（１）で表されるアミン化
合物を含有する。本発明の有機電界発光素子において使
用することができる本発明の一般式（１）で表されるア
ミン化合物以外の正孔注入輸送機能を有する化合物とし
ては、トリアリールアミン誘導体（例えば、４，４’−
ビス〔Ｎ−フェニル−Ｎ−（４”−メチルフェニル）ア
ミノ〕ビフェニル、４，４’−ビス〔Ｎ−フェニル−Ｎ
−（３”−メチルフェニル）アミノ〕ビフェニル、４，
４’−ビス〔Ｎ−フェニル−Ｎ−（３”−メトキシフェ
ニル）アミノ〕ビフェニル、４，４’−ビス〔Ｎ−フェ
ニル−Ｎ−（１”−ナフチル）アミノ〕ビフェニル、
３，３’−ジメチル−４，４’−ビス〔Ｎ−フェニル−
Ｎ−（３”−メチルフェニル）アミノ〕ビフェニル、
１，１−ビス〔４’−［Ｎ，Ｎ−ジ（４”−メチルフェ
ニル）アミノ］フェニル〕シクロヘキサン、９，１０−
ビス〔Ｎ−（４’−メチルフェニル）−Ｎ−（４”−ｎ
−ブチルフェニル）アミノ〕フェナントレン、３，８−
ビス（Ｎ，Ｎ−ジフェニルアミノ）−６−フェニルフェ
ナントリジン、４−メチル−Ｎ，Ｎ−ビス〔４”、
４”’−ビス［Ｎ’，Ｎ’−ジ（４−メチルフェニル）
アミノ］ビフェニル−４−イル〕アニリン、Ｎ，Ｎ’−
ビス〔４−（ジフェニルアミノ）フェニル〕−Ｎ，Ｎ’
−ジフェニル−１，３−ジアミノベンゼン、Ｎ，Ｎ’−
ビス〔４−（ジフェニルアミノ）フェニル〕−Ｎ，Ｎ’
−ジフェニル−１，４−ジアミノベンゼン、５，５”−
ビス〔４−（ビス［４−メチルフェニル］アミノ〕フェ
ニル−２，２’：５’，２”−ターチオフェン、１，
３，５−トリス（ジフェニルアミノ）ベンゼン、４，
４’，４”−トリス（Ｎ−カルバゾリイル）トリフェニ
ルアミン、４，４’，４”−トリス〔Ｎ，Ｎ−ビス
（４”’−tert−ブチルビフェニル−４””−イル）ア
ミノ〕トリフェニルアミン、１，３，５−トリス〔Ｎ−
（４’−ジフェニルアミノ〕ベンゼンなど、ポリチオフ
ェンおよびその誘導体、ポリ−Ｎ−ビニルカルバゾール
およびその誘導体がより好ましい。The organic electroluminescent device of the present invention preferably contains the amine compound represented by the general formula (1) in the hole injecting and transporting layer. As the compound having a hole injecting and transporting function other than the amine compound represented by the general formula (1) of the present invention which can be used in the organic electroluminescent device of the present invention, a triarylamine derivative (for example, 4,4) is used. '-
Bis [N-phenyl-N- (4 ″ -methylphenyl) amino] biphenyl, 4,4′-bis [N-phenyl-N
-(3 "-methylphenyl) amino] biphenyl, 4,
4'-bis [N-phenyl-N- (3 "-methoxyphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N- (1" -naphthyl) amino] biphenyl,
3,3'-Dimethyl-4,4'-bis [N-phenyl-
N- (3 "-methylphenyl) amino] biphenyl,
1,1-bis [4 '-[N, N-di (4 "-methylphenyl) amino] phenyl] cyclohexane, 9,10-
Bis [N- (4'-methylphenyl) -N- (4 "-n
-Butylphenyl) amino] phenanthrene, 3,8-
Bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-N, N-bis [4 ″,
4 "'-bis [N', N'-di (4-methylphenyl)
Amino] biphenyl-4-yl] aniline, N, N'-
Bis [4- (diphenylamino) phenyl] -N, N '
-Diphenyl-1,3-diaminobenzene, N, N'-
Bis [4- (diphenylamino) phenyl] -N, N '
-Diphenyl-1,4-diaminobenzene, 5,5 "-
Bis [4- (bis [4-methylphenyl] amino] phenyl-2,2 ′: 5 ′, 2 ″ -terthiophene, 1,
3,5-tris (diphenylamino) benzene, 4,
4 ', 4 "-tris (N-carbazolyyl) triphenylamine, 4,4', 4" -tris [N, N-bis (4 "'-tert-butylbiphenyl-4""-yl) amino] tri Phenylamine, 1,3,5-tris [N-
More preferred are polythiophene and its derivatives, such as (4′-diphenylamino] benzene, and poly-N-vinylcarbazole and its derivatives.
【００６５】一般式（１）で表されるアミン化合物と他
の正孔注入機能を有する化合物を併用する場合、正孔注
入輸送層中に占める一般式（１）で表されるアミン化合
物の含有量は、好ましくは、０．１重量％以上、より好
ましくは、０．５〜９９．９重量％、さらに好ましくは
３〜９７重量％である。When the amine compound represented by the general formula (1) and another compound having a hole injecting function are used in combination, the amine compound represented by the general formula (1) is contained in the hole injecting and transporting layer. The amount is preferably 0.1% by weight or more, more preferably 0.5 to 99.9% by weight, and further preferably 3 to 97% by weight.
【００６６】発光層４は、正孔および電子の注入機能、
それらの輸送機能、正孔と電子の再結合により励起子を
生成させる機能を有する化合物を含有する層である。発
光層は、一般式（１）で表されるアミン化合物および／
または他の発光機能を有する化合物を少なくとも一種用
いて形成することができる。The light emitting layer 4 has a function of injecting holes and electrons,
It is a layer containing a compound having a function of transporting them and a function of generating excitons by recombination of holes and electrons. The light emitting layer comprises an amine compound represented by the general formula (1) and /
Alternatively, it can be formed using at least one compound having another light-emitting function.
【００６７】一般式（１）で表されるアミン化合物以外
の発光機能を有する化合物としては、例えば、アクリド
ン誘導体、キナクリドン誘導体、ジケトピロロピロール
誘導体、多環芳香族化合物〔例えば、ルブレン、アント
ラセン、テトラセン、ピレン、ペリレン、クリセン、デ
カサイクレン、コロネン、テトラフェニルシクロペンタ
ジエン、ペンタフェニルシクロペンタジエン、９，１０
−ジフェニルアントラセン、９，１０−ビス（フェニル
エチニル）アントラセン、１，４−ビス（９’−エチニ
ルアントセニル）ベンゼン、４，４’−ビス（９”−エ
チニルアントラセニル）ビフェニル、ジベンゾ［f,f］
ジインデノ［1,2,3-cd：1',2',3'-lm］ペリレン誘導
体〕、トリアリールアミン誘導体（例えば、正孔注入輸
送機能を有する化合物として前述した化合物を挙げるこ
とができる）、有機金属錯体〔例えば、トリス（８−キ
ノリノラート）アルミニウム、ビス（１０−ベンゾ
［ｈ］キノリノラート）ベリリウム、２−（２’−ヒド
ロキシフェニル）ベンゾチアゾールの亜鉛塩、４−ヒド
ロキシアクリジンの亜鉛塩、３−ヒドロキシフラボンの
亜鉛塩、５−ヒドロキシフラボンのベリリウム塩、５−
ヒドロキシフラボンのアルミニウム塩〕、スチルベン誘
導体〔例えば、１，１，４，４−テトラフェニル−１，
３−ブタジエン、４，４’−ビス（２，２−ジフェニル
ビニル）ビフェニル、４，４’−ビス［（１，１，２−
トリフェニル）エテニル］ビフェニル〕、クマリン誘導
体（例えば、クマリン１、クマリン６、クマリン７、ク
マリン３０、クマリン１０６、クマリン１３８、クマリ
ン１５１、クマリン１５２、クマリン１５３、クマリン
３０７、クマリン３１１、クマリン３１４、クマリン３
３４、クマリン３３８、クマリン３４３、クマリン５０
０）、ピラン誘導体（例えば、ＤＣＭ１、ＤＣＭ２）、
オキサゾン誘導体（例えば、ナイルレッド）、ベンゾチ
アゾール誘導体、ベンゾオキサゾール誘導体、ベンゾイ
ミダゾール夕動体、ピラジン誘導体、ケイ皮酸エステル
誘導体、ポリ−Ｎ−ビニルカルバゾールおよびその誘導
体、ポリチオフェンおよびその誘導体、ポリフェニレン
およびその誘導体、ポリフルオレンおよびその誘導体、
ポリフェニレンビニレンおよびその誘導体、ポリビフェ
ニレンビニレンおよびその誘導体、ポリターフェニレン
ビニレンおよびその誘導体、ポリナフチレンビニレンお
よびその誘導体、ポリチエニレンビニレンおよびその誘
導体等を挙げることができる。一般式（１）で表される
アミン化合物以外の発光機能を有する化合物としては、
アクリドン誘導体、キナクリドン誘導体、多環芳香族化
合物、トリアリールアミン誘導体、有機金属錯体および
スチルベン誘導体が好ましく、多環芳香族化合物、有機
金属錯体がより好ましい。Examples of the compound having a light emitting function other than the amine compound represented by the general formula (1) include acridone derivatives, quinacridone derivatives, diketopyrrolopyrrole derivatives, polycyclic aromatic compounds [eg rubrene, anthracene, Tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10
-Diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthocenyl) benzene, 4,4'-bis (9 "-ethynylanthracenyl) biphenyl, dibenzo [ f, f]
Diindeno [1,2,3-cd: 1 ', 2', 3'-lm] perylene derivative], triarylamine derivative (for example, the compounds described above can be mentioned as the compound having a hole injecting and transporting function) An organometallic complex [for example, tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, zinc salt of 2- (2′-hydroxyphenyl) benzothiazole, zinc salt of 4-hydroxyacridine, Zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, 5-
Aluminum salt of hydroxyflavone], stilbene derivative [eg 1,1,4,4-tetraphenyl-1,
3-butadiene, 4,4'-bis (2,2-diphenylvinyl) biphenyl, 4,4'-bis [(1,1,2-
Triphenyl) ethenyl] biphenyl], coumarin derivative (for example, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, coumarin 138, coumarin 151, coumarin 152, coumarin 153, coumarin 307, coumarin 311, coumarin 314, coumarin) Three
34, Coumarin 338, Coumarin 343, Coumarin 50
0), a pyran derivative (eg, DCM1, DCM2),
Oxazone derivative (for example, Nile red), benzothiazole derivative, benzoxazole derivative, benzimidazole derivative, pyrazine derivative, cinnamic acid ester derivative, poly-N-vinylcarbazole and its derivative, polythiophene and its derivative, polyphenylene and its derivative , Polyfluorene and its derivatives,
Examples thereof include polyphenylene vinylene and its derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and its derivatives, polythienylene vinylene and its derivatives, and the like. As the compound having a light emitting function other than the amine compound represented by the general formula (1),
An acridone derivative, a quinacridone derivative, a polycyclic aromatic compound, a triarylamine derivative, an organometallic complex and a stilbene derivative are preferable, and a polycyclic aromatic compound and an organometallic complex are more preferable.
【００６８】本発明の有機電界発光素子は、発光層に一
般式（１）で表されるアミン化合物を含有していること
が好ましい。In the organic electroluminescent device of the present invention, it is preferable that the light emitting layer contains an amine compound represented by the general formula (1).
【００６９】一般式（１）で表される化合物と一般式
（１）で表されるアミン化合物以外の発光機能を有する
化合物を併用する場合、発光層中に占める一般式（１）
で表される化合物の割合は、好ましくは、０．００１〜
９９．９９９重量％に調節する。When the compound represented by the general formula (1) and the compound having a light emitting function other than the amine compound represented by the general formula (1) are used in combination, the general formula (1) occupies the light emitting layer.
The proportion of the compound represented by is preferably 0.001 to
Adjust to 99.999% by weight.
【００７０】また、発光層は、J.Appl.Phys.,65、3610
（1989）、特開平５−２１４３３２号公報に記載のよう
に、ホスト化合物とゲスト化合物（ドーパント）から形
成することも可能である。Further, the light emitting layer is composed of J. Appl. Phys., 65 , 3610.
(1989), JP-A-5-214332, it is also possible to form from a host compound and a guest compound (dopant).
【００７１】一般式（１）で表されるアミン化合物は発
光層のホスト化合物として使用することもでき、またゲ
スト化合物として使用することも可能である。一般式
（１）で表されるアミン化合物をホスト化合物として発
光層を形成する場合、ゲスト化合物としては、例えば、
前記のほかの発光機能を有する化合物を挙げることがで
き、中でも多環芳香族化合物は好ましい。The amine compound represented by the general formula (1) can be used as a host compound in the light emitting layer and also as a guest compound. When the light emitting layer is formed by using the amine compound represented by the general formula (1) as a host compound, examples of the guest compound include:
Other compounds having a light emitting function can be mentioned, and among them, polycyclic aromatic compounds are preferable.
【００７２】一般式（１）で表されるアミン化合物をホ
スト化合物として発光層を形成する場合、一般式（１）
で表されるアミン化合物に対して、ゲスト化合物は、好
ましくは、０．００１から４０重量％、より好ましく
は、０．０１〜３０重量％、さらに好ましくは０．１〜
２０重量％使用する発光層は、一般式（１）で表される
アミン化合物をホスト材料として、一般式（１）で表さ
れるアミン化合物以外の発光機能を有する化合物を少な
くとも１種ゲスト材料として使用して形成することがで
きる。When the light emitting layer is formed by using the amine compound represented by the general formula (1) as a host compound, the general formula (1)
The guest compound is preferably 0.001 to 40% by weight, more preferably 0.01 to 30% by weight, still more preferably 0.1 to 40% by weight with respect to the amine compound represented by
The light emitting layer used in an amount of 20% by weight has an amine compound represented by the general formula (1) as a host material and at least one compound having a light emitting function other than the amine compound represented by the general formula (1) as a guest material. Can be formed using.
【００７３】本発明の有機電界発光素子は、好ましく
は、発光層に一般式（１）で表されるアミン化合物をホ
スト材料として含有する。The organic electroluminescent device of the present invention preferably contains the amine compound represented by the general formula (1) in the light emitting layer as a host material.
【００７４】一般式（１）で表されるアミン化合物ホス
ト材料として、他の発光機能を有する化合物と併用する
場合、発光層中に占める一般式（１）で表されるアミン
化合物は、好ましくは、４０．０％〜９９．９％であ
り、より好ましくは、６０．０〜９９．９重量％であ
る。When the amine compound host material represented by the general formula (1) is used in combination with another compound having a light emitting function, the amine compound represented by the general formula (1) in the light emitting layer is preferably 40.0% to 99.9%, and more preferably 60.0 to 99.9% by weight.
【００７５】ゲスト材料の使用量は、一般式（１）で表
されるアミン化合物に対して０．００１〜４０重量％、
好ましくは、０．０５〜３０重量％、より好ましくは、
０．１〜２０重量％である。また、ゲスト材料は、単独
で使用してもよく、複数併用してもよい。The guest material is used in an amount of 0.001 to 40% by weight based on the amine compound represented by the general formula (1).
Preferably 0.05 to 30% by weight, more preferably
It is 0.1 to 20% by weight. The guest materials may be used alone or in combination of two or more.
【００７６】一般式（１）で表されるアミン化合物を、
ゲスト材料として用いて発光層を形成する場合、ホスト
材料としては、多環芳香族化合物、トリアリールアミン
誘導体、有機金属錯体およびスチルベン誘導体が好まし
く、多環芳香族化合物、有機金属錯体がより好ましい。The amine compound represented by the general formula (1) is
When the light emitting layer is formed using the guest material, the host material is preferably a polycyclic aromatic compound, a triarylamine derivative, an organometallic complex or a stilbene derivative, and more preferably a polycyclic aromatic compound or an organometallic complex.
【００７７】一般式（１）で表されるアミン化合物をゲ
スト材料として使用する場合、一般式（１）で表される
アミン化合物を、好ましくは、０．００１〜４０重量
％、より好ましくは、０．０１〜３０重量％、さらに好
ましくは、０．１〜２０重量％使用する。When the amine compound represented by the general formula (1) is used as a guest material, the amine compound represented by the general formula (1) is preferably 0.001 to 40% by weight, more preferably 0.01 to 30% by weight, more preferably 0.1 to 20% by weight is used.
【００７８】電子注入輸送層５は、陰極からの電子の注
入を容易にする機能および／または注入された電子を輸
送する機能を有する化合物を含有する層である。The electron injection / transport layer 5 is a layer containing a compound having a function of facilitating the injection of electrons from the cathode and / or a function of transporting the injected electrons.
【００７９】電子注入輸送層に使用される電子注入機能
を有する化合物としては、例えば、有機金属錯体、オキ
サジアゾール誘導体、トリアゾール誘導体、トリアジン
誘導体、ペリレン誘導体、キノリン誘導体、キノキサリ
ン誘導体、ジフェニルキノン誘導体、ニトロ置換フルオ
レノン誘導体、チオピランジオキサイド誘導体などを挙
げることができる。また、有機金属錯体としては、例え
ば、トリス（８−キノリノラート）アルミニウム等の有
機アルミニウム錯体、ビス（１０−ベンゾ［ｈ］キノリ
ノラート）ベリリウム等の有機ベリリウム錯体、５−ヒ
ドロキシフラボンのベリリウム塩、５−ヒドロキシフラ
ボンのアルミニウム塩等を挙げることができる。好まし
くは、有機アルミニウム錯体であり、より好ましくは、
置換または未置換の８−キノリノラート配位子を有する
有機アルミニウム錯体である。Examples of the compound having an electron injecting function used in the electron injecting and transporting layer include organic metal complexes, oxadiazole derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, Examples thereof include nitro-substituted fluorenone derivatives and thiopyrandioxide derivatives. As the organometallic complex, for example, an organoaluminum complex such as tris (8-quinolinolato) aluminum, an organic beryllium complex such as bis (10-benzo [h] quinolinolato) beryllium, a beryllium salt of 5-hydroxyflavone, 5- Examples thereof include aluminum salt of hydroxyflavone. It is preferably an organoaluminum complex, and more preferably
It is an organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand.
【００８０】置換または未置換の８−キノリラート配位
子を有する有機アルミニウム錯体としては、例えば、一
般式（ａ）〜一般式（ｃ）で表される化合物を挙げるこ
とができる。Examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolylate ligand include compounds represented by the general formulas (a) to (c).
【００８１】（Ｑ）3−Ａｌ （ａ）
（式中、Ｑは置換または未置換の８−キノリノラート配
位子を表す）
（Ｑ）2−Ａｌ−Ｏ−Ｌ’ （ｂ）
（式中、Ｑは置換または未置換の８−キノリノラート配
位子を表し、Ｏ−Ｌ’はフェノラート配位子を表し、
Ｌ’はフェニル基を有する炭素数６〜２４の炭化水素基
を表す）
（Ｑ）2−Ａｌ−Ｏ−Ａｌ−（Ｑ）2 （ｃ）
（式中、Ｑは置換または未置換の８−キノリノラート配
位子を表す）(Q) 3 -Al (a) (wherein Q represents a substituted or unsubstituted 8-quinolinolato ligand) (Q) 2 -Al-OL '(b) (wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand, OL 'represents a phenolate ligand,
L ′ represents a hydrocarbon group having a phenyl group and having 6 to 24 carbon atoms. (Q) 2 —Al—O—Al— (Q) 2 (c) (In the formula, Q is a substituted or unsubstituted 8- Represents a quinolinolato ligand)
【００８２】置換または未置換の８−キノリノラート配
位子を有する有機アルミニウム錯体の具体例としては、
例えば、トリス（８−キノリノラート）アルミニウム、
トリス（４−メチル−８−キノリノラート）アルミニウ
ム、トリス（５−メチル−８−キノリノラート）アルミ
ニウム、トリス（３，４−ジメチル−８−キノリノラー
ト）アルミニウム、トリス（４，５−ジメチル−８−キ
ノリノラート）アルミニウム、トリス（４，６−ジメチ
ル−８−キノリノラート）アルミニウム、ビス（２−メ
チル−８−キノリノラート）（フェノラート）アルミニ
ウム、ビス（２−メチル−８−キノリノラート）（２−
メチルフェノラート）アルミニウム、ビス（２−メチル
−８−キノリノラート）（３−メチルフェノラート）ア
ルミニウム、ビス（２−メチル−８−キノリノラート）
（４−メチルフェノラート）アルミニウム、ビス（２−
メチル−８−キノリノラート）（２−フェニルフェノラ
ート）アルミニウム、ビス（２−メチル−８−キノリノ
ラート）（３−フェニルフェノラート）アルミニウム、
ビス（２−メチル−８−キノリノラート）（４−フェニ
ルフェノラート）アルミニウム、ビス（２−メチル−８
−キノリノラート）（２，３−ジメチルフェノラート）
アルミニウム、ビス（２−メチル−８−キノリノラー
ト）（２，６−ジメチルフェノラート）アルミニウム、
ビス（２−メチル−８−キノリノラート）（３，４−ジ
メチルフェノラート）アルミニウム、ビス（２−メチル
−８−キノリノラート）（３，５−ジメチルフェノラー
ト）アルミニウム、ビス（２−メチル−８−キノリノラ
ート）（３，５−ジ-tert−ブチルフェノラート）アル
ミニウム、ビス（２−メチル−８−キノリノラート）
（２，６−ジフェニルフェノラート）アルミニウム、ビ
ス（２−メチル−８−キノリノラート）（２，４，６−
トリフェニルフェノラート）アルミニウム、ビス（２−
メチル−８−キノリノラート）（２，４，６−トリメチ
ルフェノラート）アルミニウム、ビス（２−メチル−８
−キノリノラート）（２，４，５，６−テトラメチルフ
ェノラート）アルミニウム、ビス（２−メチル−８−キ
ノリノラート）（１−ナフトラート）アルミニウム、ビ
ス（２−メチル−８−キノリノラート）（２−ナフトラ
ート）アルミニウム、ビス（２，４−ジメチル−８−キ
ノリノラート）（２−フェニルフェノラート）アルミニ
ウム、ビス（２，４−ジメチル−８−キノリノラート）
（３−フェニルフェノラート）アルミニウム、ビス
（２，４−ジメチル−８−キノリノラート）（４−フェ
ニルフェノラート）アルミニウム、ビス（２，４−ジメ
チル−８−キノリノラート）（３，５−ジメチルフェノ
ラート）アルミニウム、ビス（２，４−ジメチル−８−
キノリノラート）（３，５−ジ-tert−ブチルフェノラ
ート）アルミニウム、Specific examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolinolate ligand include:
For example, tris (8-quinolinolato) aluminum,
Tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl-8-quinolinolato) aluminum, tris (3,4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) Aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-8-quinolinolato) (phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-
Methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(4-Methylphenolate) aluminum, bis (2-
Methyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolato) aluminum,
Bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum, bis (2-methyl-8)
-Quinolinolate) (2,3-dimethylphenolate)
Aluminum, bis (2-methyl-8-quinolinolato) (2,6-dimethylphenolate) aluminum,
Bis (2-methyl-8-quinolinolato) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8-) Quinolinolato) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato)
(2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-
Triphenylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8)
-Quinolinolate) (2,4,5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolate) (2-naphtholate ) Aluminum, bis (2,4-dimethyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato)
(3-Phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenolate ) Aluminum, bis (2,4-dimethyl-8-
Quinolinoleate) (3,5-di-tert-butylphenolate) aluminum,
【００８３】ビス（２−メチル−８−キノリノラート）
アルミニウム−μ−オキソ−ビス（２−メチル−８−キ
ノリノラート）アルミニウム、ビス（２，４−ジメチル
−８−キノリノラート）アルミニウム−μ−オキソ−ビ
ス（２，４−ジメチル−８−キノリノラート）アルミニ
ウム、ビス（２−メチル−４−エチル−８−キノリノラ
ート）アルミニウム−μ−オキソ−ビス（２−メチル−
４−エチル−８−キノリノラート）アルミニウム、ビス
（２−メチル−４−メトキシ−８−キノリノラート）ア
ルミニウム−μ−オキソ−ビス（２−メチル−４−メト
キシ−８−キノリノラート）アルミニウム、ビス（２−
メチル−５−シアノ−８−キノリノラート）アルミニウ
ム−μ−オキソ−ビス（２−メチル−５−シアノ−８−
キノリノラート）アルミニウム、ビス（２−メチル−５
−トリフルオロメチル−８−キノリノラート）アルミニ
ウム−μ−オキソ−ビス（２−メチル−５−トリフルオ
ロメチル−８−キノリノラート）アルミニウムを挙げる
ことができる。電子注入機能を有する化合物は単独で使
用してもよく、また複数併用してもよい。Bis (2-methyl-8-quinolinolate)
Aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolato) aluminum, Bis (2-methyl-4-ethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-)
4-Ethyl-8-quinolinolato) aluminum, bis (2-methyl-4-methoxy-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-4-methoxy-8-quinolinolato) aluminum, bis (2-
Methyl-5-cyano-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-
Quinolinolato) aluminum, bis (2-methyl-5)
-Trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum. The compound having an electron injection function may be used alone or in combination of two or more.
【００８４】陰極６としては、比較的仕事関数の小さい
金属、合金または導電性化合物を電極材料として使用す
ることが好ましい。陰極に使用する電極材料としては、
例えば、リチウム、リチウム−インジウム合金、ナトリ
ウム、ナトリウム−カリウム合金、カルシウム、マグネ
シウム、マグネシウム−銀合金、マグネシム−インジウ
ム合金、インジウム、ルテニウム、チタニウム、マンガ
ン、イットリウム、アルミニウム、アルミニウム−リチ
ウム合金、アルミニウム−カルシウム合金、アルミニウ
ム−マグネシウム合金、グラファイト薄を挙げることが
できる。これらの電極材料は単独で使用してもよく、ま
た複数併用してもよい。陰極はこれらの電極材料を、例
えば、蒸着法、スパッタリング法、イオン蒸着法、イオ
ンプレーティング法、クラスターイオンビーム法により
電子注入輸送層の上に形成することができる。For the cathode 6, it is preferable to use a metal, alloy or conductive compound having a relatively small work function as an electrode material. As the electrode material used for the cathode,
For example, lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium, manganese, yttrium, aluminum, aluminum-lithium alloy, aluminum-calcium. Alloys, aluminum-magnesium alloys, and graphite thin can be mentioned. These electrode materials may be used alone or in combination. For the cathode, these electrode materials can be formed on the electron injecting and transporting layer by, for example, a vapor deposition method, a sputtering method, an ion vapor deposition method, an ion plating method, or a cluster ion beam method.
【００８５】また、陰極は一層構造であってもよく、多
層構造であってもよい。陰極のシート電気抵抗は数百Ω
／□以下とするのが好ましい。陰極の厚みは、使用する
電極材料にもよるが、通常５〜１０００ｎｍ、好ましく
は、１０〜５００ｎｍとする。本発明の有機電界発光素
子の発光を高率よく取り出すために、陽極または陰極の
少なくとも一方の電極は、透明ないし半透明であること
が好ましく、一般に、発光光の透過率が７０％以上とな
るように陽極または陰極の材料、厚みを設定することが
好ましい。The cathode may have a single-layer structure or a multi-layer structure. Sheet electric resistance of the cathode is several hundred Ω
/ □ or less is preferable. The thickness of the cathode depends on the electrode material used, but is usually 5 to 1000 nm, preferably 10 to 500 nm. In order to extract light emitted from the organic electroluminescence device of the present invention with high efficiency, at least one of the anode and the cathode is preferably transparent or semitransparent, and generally the transmittance of emitted light is 70% or more. Thus, it is preferable to set the material and thickness of the anode or cathode.
【００８６】また、本発明の有機電界発光素子は、正孔
注入輸送層、発光層および電子注入輸送層の少なくとも
一層中に、一重項酸素クンチャーを含有していてもよ
い。一重項酸素クエンチャーとしては、特に限定される
ものではないが、例えば、ルブレン、ニッケル錯体、ジ
フェニルイソベンゾフランが挙げられ、好ましくは、ル
ブレンである。In the organic electroluminescent device of the present invention, at least one of the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer may contain a singlet oxygen quencher. The singlet oxygen quencher is not particularly limited, but examples thereof include rubrene, nickel complex, and diphenylisobenzofuran, and rubrene is preferable.
【００８７】一重項酸素クエンチャーが含有されている
層としては、特に限定されるものではないが、好ましく
は、発光層または正孔注入輸送層であり、より好ましく
は、正孔注入輸送層である。尚、正孔注入輸送層に一重
項酸素クエンチャーを含有させる場合、正孔注入輸送層
中に均一に含有させてもよく、正孔注入輸送層と隣接す
る層（例えば、発光層、発光機能を有する電子注入輸送
層）の近傍に含有させてもよい。The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injecting and transporting layer, more preferably a hole injecting and transporting layer. is there. When the hole injecting and transporting layer contains a singlet oxygen quencher, it may be uniformly contained in the hole injecting and transporting layer, and a layer adjacent to the hole injecting and transporting layer (for example, a light emitting layer, a light emitting function). May be included in the vicinity of the electron injecting and transporting layer).
【００８８】一重項酸素クエンチャーの含有量として
は、含有される層（例えば、正孔注入輸送層）を構成す
る全体量の０．０１〜５０重量％、好ましくは、０．０
５〜３０重量％、より好ましくは、０．１〜２０重量％
である。The content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.0 to 50% by weight based on the total amount of the layer (for example, the hole injecting and transporting layer) to be contained.
5 to 30% by weight, more preferably 0.1 to 20% by weight
Is.
【００８９】正孔注入輸送層、発光層、電子注入輸送層
の形成方法に関しては、特に限定されるものではなく、
例えば、真空蒸着法、イオン化蒸着法、溶液塗布法（例
えば、スピンコート法、キャスト法、デイップコート
法、バーコート法、ロールコート法、ラングミュア・ブ
ロジェット法、インクジェット法）を使用することがで
きる。真空蒸着法により正孔注入輸送層、発光層、電子
注入輸送層等の各層を形成する場合、真空蒸着の条件
は。、特に限定されるものではないが、通常、１０ -5Ｔ
ｏｒｒ程度以下の真空下で、５０〜５００℃程度のボー
ト温度（蒸着源温度）、−５０〜３００℃程度の基板温
度で、０．００５〜５０ｎｍ／sec程度の蒸着速度で実
施することが好ましい。この場合、正孔注入輸送層、発
光層、電子注入輸送層等の各層は、真空下で、連続して
形成することが好ましい。連続で形成することにより諸
特性に優れた有機電界発光素子を製造することが可能と
なる。真空蒸着法により、正孔注入輸送層、発光層、電
子注入輸送層等の各層を、複数の化合物を使用して形成
する場合、化合物を入れた各ボートを個別に温度制御し
て、共蒸着することが好ましい。Hole injecting / transporting layer, light emitting layer, electron injecting / transporting layer
The method of forming is not particularly limited,
For example, vacuum deposition method, ionization deposition method, solution coating method (example
For example, spin coating, casting, dip coating
Method, bar coat method, roll coat method, Langmuir Bou
Can be used.
Wear. Hole injecting and transporting layer, emitting layer, electron by vacuum evaporation method
When forming each layer such as injecting and transporting layer, vacuum deposition conditions
Ha. , But is not particularly limited, usually 10 -FiveT
Under a vacuum of about orr or less, a bow of about 50 to 500 ° C
Temperature (deposition source temperature), substrate temperature of about -50 to 300 ° C
Deposition rate of 0.005 to 50 nm / sec.
It is preferable to apply. In this case, the hole injection transport layer
Each layer such as the light layer and the electron injecting and transporting layer is continuously placed under vacuum.
It is preferably formed. By continuously forming
It is possible to manufacture organic electroluminescent devices with excellent characteristics.
Become. By vacuum evaporation method, hole injection transport layer, light emitting layer,
Each layer such as child injection transport layer is formed using multiple compounds
Temperature control for each boat containing compound
Therefore, co-evaporation is preferable.
【００９０】溶液塗布法により各層を形成する場合、各
層を形成する成分あるいはその成分とバインダー樹脂等
とを、溶媒に溶解または分散させて塗布液とする。溶媒
としては、例えば、有機溶媒（ヘキサン、オクタン、デ
カン、トルエン、キシレン、エチルベンゼン、１−メチ
ルナフタレン等の炭化水素系溶媒、アセトン、メチルエ
チルケトン、メチルイソブチルケトン、シクロヘキサノ
ン等のケトン系溶媒、ジクロロメタン、クロロホルム、
テトラクロロメタン、ジクロロエタン、トリクロロエタ
ン、テトラクロロエタン、クロロベンゼン、ジクロロベ
ンゼン、クロロトルエン等のハロゲン化炭化水素系溶
媒、酢酸エチル、酢酸ブチル、酢酸アミル、乳酸エチル
等のエステル系溶媒、メタノール、プロパノール、ブタ
ノール、ペンタノール、ヘキサノール、シクロヘキサノ
ール、メチルセロソルブ、エチルセロソルブ、エチレン
グリコール等のアルコール系溶媒、ジブチルエーテル、
テトラヒドロフラン、ジオキサン、ジメトキシエタン、
アニソール等のエーテル系溶媒、Ｎ，Ｎ−ジメチルホル
ムアミド、Ｎ，Ｎ−ジメチルアセトアミド、１−メチル
−２−ピロリドン、１，３−ジメチル−２−イミダゾリ
ジノン、ジメチルスルホキシド等の極性溶媒）、水を挙
げることができる。溶媒は単独で使用してもよく、また
複数併用してもよい。正孔注入輸送層、発光層、電子注
入輸送層の各層の成分を溶媒に分散させる場合には、分
散方法として、例えば、ボールミル、サンドミル、ペイ
ントシェーカー、アトライター、ホモジナイザー等を使
用して微粒子状に分散する方法を使用することができ
る。When each layer is formed by the solution coating method, the component forming each layer or the component and the binder resin are dissolved or dispersed in a solvent to prepare a coating liquid. As the solvent, for example, an organic solvent (hexane, octane, decane, toluene, xylene, ethylbenzene, a hydrocarbon solvent such as 1-methylnaphthalene, a ketone solvent such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, dichloromethane, chloroform) ,
Tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, halogenated hydrocarbon solvents such as chlorotoluene, ethyl acetate, butyl acetate, amyl acetate, ester solvents such as ethyl lactate, methanol, propanol, butanol, Alcohol solvents such as pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, ethylene glycol, dibutyl ether,
Tetrahydrofuran, dioxane, dimethoxyethane,
Ether solvent such as anisole, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide), water Can be mentioned. The solvent may be used alone or in combination of two or more. When the components of the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer are dispersed in a solvent, for example, a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like is used to form a fine particle. Can be used.
【００９１】また、正孔注入輸送層、発光層、電子注入
輸送層等の各層に使用しうるバインダー樹脂としては、
ポリ−Ｎ−ビニルカルバゾール、ポリアリーレート、ポ
リスチレン、ポリエステル、ポリシロキサン、ポリメチ
ルメタクリレート、ポリメチルアクリレート、ポリエー
テル、ポリカーボネート、ポリアミド、ポリイミド、ポ
リアミドイミド、ポリパラキシレン、ポリエチレン、ポ
リフェニレンオキサイド、ポリエーテルスルホン、ポリ
アニリンおよびその誘導体、ポリチオフェンおよびその
誘導体、ポリフェニレンビニレンおよびその誘導体、ポ
リフルオレンおよびその誘導体、ポリチエニレンビニレ
ンおよびその誘導体などの高分子化合物を挙げることが
できる。バインダー樹脂は単独で使用してもよく、ま
た、複数併用してもよい。塗布液の濃度は、特に限定さ
れるものではないが、実施する塗布法により所望の厚み
を作製するに適した濃度範囲に設定することができ、通
常、０．１〜５０重量％、好ましくは、１〜３０重量％
に設定する。バインダー樹脂を使用する場合、その使用
量は特に限定されるものではないが、通常、正孔注入輸
送層、発光層、電子注入輸送層等の各層を形成する成分
とバインダー樹脂の総量に対してバインダー樹脂の含有
率が（一層型の素子を形成する場合には各成分の総量に
対して）、５〜９９．９重量％、好ましくは、１０〜９
９重量％となるように使用する。Further, as a binder resin which can be used in each layer such as a hole injecting and transporting layer, a light emitting layer, an electron injecting and transporting layer,
Poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethylmethacrylate, polymethylacrylate, polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyether sulfone , Polyaniline and its derivatives, polythiophene and its derivatives, polyphenylene vinylene and its derivatives, polyfluorene and its derivatives, polythienylene vinylene and its derivatives, and the like. The binder resins may be used alone or in combination of two or more. The concentration of the coating liquid is not particularly limited, but can be set within a concentration range suitable for producing a desired thickness by the coating method to be performed, and is usually 0.1 to 50% by weight, preferably , 1 to 30% by weight
Set to. When a binder resin is used, the amount thereof is not particularly limited, but is usually relative to the total amount of the component and the binder resin forming each layer such as the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer. The binder resin content (based on the total amount of each component in the case of forming a one-layer type element) is 5 to 99.9% by weight, preferably 10 to 9
It is used so as to be 9% by weight.
【００９２】正孔注入輸送層、発光層、電子注入輸送層
等の各層の膜厚は、特に限定されるものではないが、通
常、５ｎｍ〜５μｍとする。The thickness of each layer such as the hole injecting / transporting layer, the light emitting layer and the electron injecting / transporting layer is not particularly limited, but is usually 5 nm to 5 μm.
【００９３】また、上記の条件で作製した本発明の有機
電界発光素子は、酸素や水分等との接触を防止する目的
で、保護層（封止層）を設けたり、また、素子を不活性
物質中（例えば、パラフィン、流動パラフィン、シリコ
ンオイル、フルオロカーボン油、ゼオライト含有フルオ
ロカーボン油）に封入して保護することができる。保護
層に使用する材料としては、例えば、有機高分子材料
（例えば、フッ素樹脂、エポキシ樹脂、シリコーン樹
脂、エポキシシリコーン樹脂、ポリスチレン、ポリエス
テル、ポリカーボネート、ポリアミド、ポリイミド、ポ
リアミドイミド、ポリパラキシレン、ポリエチレン、ポ
リフェニレンオキサイド）、無機材料（例えば、ダイア
モンド薄膜、アモルファスシリカ、電気絶縁性ガラス、
金属酸化物、金属窒化物、金属炭化物、金属硫化物）、
さらには、光硬化性樹脂を挙げることができる。保護層
に使用する材料は単独で使用してもよく、また複数併用
してもよい。保護層は一層構造であってもよく、また多
層構造であってもよい。The organic electroluminescent device of the present invention manufactured under the above conditions is provided with a protective layer (sealing layer) or is inactive for the purpose of preventing contact with oxygen, moisture and the like. It can be protected by enclosing it in a substance (for example, paraffin, liquid paraffin, silicone oil, fluorocarbon oil, zeolite-containing fluorocarbon oil). Examples of the material used for the protective layer include organic polymer materials (for example, fluororesin, epoxy resin, silicone resin, epoxysilicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, Polyphenylene oxide), inorganic materials (for example, diamond thin film, amorphous silica, electrically insulating glass,
Metal oxide, metal nitride, metal carbide, metal sulfide),
Furthermore, a photocurable resin can be mentioned. The materials used for the protective layer may be used alone or in combination. The protective layer may have a single layer structure or a multilayer structure.
【００９４】また、本発明の有機電界発光素子は、電極
に保護膜として金属酸化物膜（例えば、酸化アルミニウ
ム膜）、金属フッ化膜を設けることもできる。Further, in the organic electroluminescence device of the present invention, a metal oxide film (eg, aluminum oxide film) or a metal fluoride film can be provided on the electrode as a protective film.
【００９５】本発明の有機電界発光素子は、陽極の表面
に界面層（中間層）を設けることもできる。界面層の材
質としては、有機リン化合物、ポリシラン、芳香族アミ
ン誘導体、フタロシアニン誘導体等を挙げることができ
る。In the organic electroluminescent element of the present invention, an interface layer (intermediate layer) may be provided on the surface of the anode. Examples of the material of the interface layer include organic phosphorus compounds, polysilanes, aromatic amine derivatives, and phthalocyanine derivatives.
【００９６】さらに、電極、例えば、陽極はその表面
を、酸、アンモニア／過酸化水素、あるいはプラズマで
処理して使用することもできる。Further, an electrode such as an anode may be used by treating the surface thereof with an acid, ammonia / hydrogen peroxide or plasma.
【００９７】本発明の有機電界発光素子は、通常、直流
駆動型の素子として使用することができるが、交流駆動
型の素子としても使用することができる。また、本発明
の有機電界発光素子は、セグメント型、単純マトリック
駆動型等のパッシブ駆動型であってもよく、ＴＦＴ（薄
膜トランジスタ）型、ＭＩＭ（メタル−インスレーター
−メタル）型等のアクティブ駆動型であってもよい。駆
動電圧は通常、２〜３０Ｖである。本発明の有機電界発
光素子は、パネル型光源（例えば、時計、液晶パネル等
のバックライト）、各種の発光素子（例えば、ＬＥＤ等
の発光素子の代替）、各種の表示素子〔例えば、情報表
示素子（パソコンモニター、携帯電話・携帯端末用表示
素子）〕、各種の標識、各種のセンサーなどに使用する
ことができる。The organic electroluminescent device of the present invention can be usually used as a DC drive type device, but can also be used as an AC drive type device. Further, the organic electroluminescent element of the present invention may be of a passive drive type such as a segment type or a simple matrix drive type, or an active drive type such as a TFT (thin film transistor) type or a MIM (metal-insulator-metal) type. May be The drive voltage is usually 2 to 30V. The organic electroluminescent device of the present invention includes a panel type light source (for example, a backlight such as a watch and a liquid crystal panel), various light emitting devices (for example, a light emitting device such as an LED), and various display devices [for example, information display. It can be used for devices (PC monitors, display devices for mobile phones and mobile terminals), various signs, various sensors, etc.
【００９８】[0098]
【実施例】以下、実施例を挙げて本発明をさらに詳細に
説明するが、本発明は、以下の実施例に限定されるもの
ではない。The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples.
【００９９】実施例１：例示化合物１の製造
：Ｎ−フェニル−６−ブロモ−２−ナフチルアミンの
製造
６−ブロモ−２−ナフトール１２８ｇ、アニリン２００
ｍｌ、キシレン２００ｍｌおよびｐ−トルエンスルホン
酸・一水和物２１．６ｇよりなる混合物を窒素雰囲気下
で還流しながら加熱した。キシレンを蒸留除去して、還
流温度を１９０℃まで上げ、さらに、同温度で５時間加
熱攪拌した。その後、８５℃まで冷却し、無水酢酸ナト
リウム１４．８ｇおよびエタノール４００ｍｌを添加し
た。混合物を還流しながら１時間攪拌し、その後、溶液
を５℃に冷却した。析出した固体をろ別し、エタノール
で洗浄した後、吸引乾燥した。次ぎに、固形物を温水６
００ｍｌに加えて再度スラリーとし、８０℃でスラッジ
した後、固形物をろ別し、無色結晶としてＮ−フェニル
−６−ブロモ−２−ナフチルアミン１４７ｇを得た。
：Ｎ，Ｎ−ジフェニル−６−ブロモ−２−ナフチルア
ミンの製造
次ぎに、Ｎ−フェニル−６−ブロモ−２−ナフチルアミ
ン２９．８ｇ、炭酸カリウム１３．８ｇヨウ化ベンゼン
５０ｇ、銅／青銅粉末５ｇ、１８−６−クラウンエーテ
ル２ｇおよびｏ−ジクロロベンゼン１００ｇよりなる混
合物を１９０℃に加熱し、同温度で１３時間加熱攪拌を
行った。その後、反応混合物を１００℃まで冷却し、ト
ルエンを添加した。さらに反応混合物を室温まで冷却
し、不溶物をろ別した後、ろ液を水洗し、ｏ−ジクロロ
ベンゼンおよびトルエンを減圧下に留去した。残渣をシ
リカゲルカラムクロマトグラフィーにより精製し、Ｎ，
Ｎ−ジフェニル−６−ブロモ−２−ナフチルアミン３１
ｇを淡黄色結晶として得た。
：Ｎ，Ｎ−ジフェニル−２−アミノ−６−ナフチルボ
ロン酸の製造
ホウ酸トリメチル６ｇおよびテトラヒドロフラン１０ｇ
よりなる混合物に−３０℃でＮ，Ｎ−ジフェニル−６−
ブロモ−２−ナフチルアミン１８．７ｇおよびマグネシ
ウム１．２ｇより調整したグリニャール試薬のテトラヒ
ドロフラン溶液を滴下した。滴下終了後、反応混合物を
室温まで昇温し、同温度で３時間攪拌した。その後、塩
酸水溶液を添加し、混合物を酸性とした後、生じた固体
をろ別した。得られたＮ，Ｎ−ジフェニル−２−アミノ
−６−ナフチルボロン酸は、特に精製せず、次の反応に
使用した。
：例示化合物１の製造
Ｎ，Ｎ−ジフェニル−４−ヨードアニリン３．７１ｇ、
Ｎ，Ｎ−ジフェニル−２−アミノ−６−ナフチルボロン
酸３．３９ｇ、炭酸ナトリウム１．６８ｇ、テトラキス
（トリフェニルホスフィン）パラジウム４０ｍｇ、トル
エン１０ｇおよび水１０ｇよりなる混合物を攪拌しなが
ら８０℃に加熱し、同温度で４時間加熱攪拌を行った。
その後、反応混合物を室温まで冷却し、トルエン相を分
離し、さらに水洗し、トルエン相からトルエンを減圧下
に留去した。得られた残渣をシリカゲルカラムクロマト
グラフィーにより精製し、さらに、ジメトキシエタンか
ら３回再結晶して、目的とする、Ｎ，Ｎ，Ｎ’，Ｎ’−
テトラフェニル− ４−（６’−アミノナフタレン−２
−イル）アニリン（例示化合物１の化合物）を淡黄色結
晶として３．９５ｇ得た。Example 1: Preparation of Exemplified Compound 1: Preparation of N-phenyl-6-bromo-2-naphthylamine 6-Bromo-2-naphthol 128 g, aniline 200
ml, xylene 200 ml and a mixture of p-toluenesulfonic acid monohydrate 21.6 g were heated under reflux under a nitrogen atmosphere. Xylene was distilled off, the reflux temperature was raised to 190 ° C., and the mixture was heated and stirred at the same temperature for 5 hours. Then, it cooled to 85 degreeC, and 14.8 g of anhydrous sodium acetate and 400 ml of ethanol were added. The mixture was stirred at reflux for 1 hour, after which the solution was cooled to 5 ° C. The deposited solid was separated by filtration, washed with ethanol, and then dried by suction. Next, the solid is mixed with warm water 6
It was added to 00 ml to make a slurry again and sludged at 80 ° C., and then the solid substance was separated by filtration to obtain 147 g of N-phenyl-6-bromo-2-naphthylamine as colorless crystals. Production of N, N-diphenyl-6-bromo-2-naphthylamine Next, 29.8 g of N-phenyl-6-bromo-2-naphthylamine, 13.8 g of potassium carbonate, 50 g of iodobenzene, 5 g of copper / bronze powder, A mixture consisting of 2 g of 18-6-crown ether and 100 g of o-dichlorobenzene was heated to 190 ° C. and stirred at the same temperature for 13 hours. Then the reaction mixture was cooled to 100 ° C. and toluene was added. The reaction mixture was further cooled to room temperature, the insoluble matter was filtered off, the filtrate was washed with water, and o-dichlorobenzene and toluene were distilled off under reduced pressure. The residue was purified by silica gel column chromatography, N,
N-diphenyl-6-bromo-2-naphthylamine 31
g was obtained as pale yellow crystals. : Preparation of N, N-diphenyl-2-amino-6-naphthylboronic acid 6 g of trimethyl borate and 10 g of tetrahydrofuran
To a mixture of N, N-diphenyl-6- at -30 ° C.
A tetrahydrofuran solution of a Grignard reagent prepared from 18.7 g of bromo-2-naphthylamine and 1.2 g of magnesium was added dropwise. After completion of dropping, the reaction mixture was heated to room temperature and stirred at the same temperature for 3 hours. Then, a hydrochloric acid aqueous solution was added to acidify the mixture, and then the generated solid was filtered off. The obtained N, N-diphenyl-2-amino-6-naphthylboronic acid was used for the next reaction without further purification. : Production of Exemplified Compound 1 3.71 g of N, N-diphenyl-4-iodoaniline,
A mixture of 3.39 g of N, N-diphenyl-2-amino-6-naphthylboronic acid, 1.68 g of sodium carbonate, 40 mg of tetrakis (triphenylphosphine) palladium, 10 g of toluene and 10 g of water was heated to 80 ° C. with stirring. Then, the mixture was heated and stirred at the same temperature for 4 hours.
Then, the reaction mixture was cooled to room temperature, the toluene phase was separated, washed with water, and the toluene was distilled off from the toluene phase under reduced pressure. The obtained residue is purified by silica gel column chromatography and further recrystallized from dimethoxyethane three times to obtain the desired N, N, N ', N'-.
Tetraphenyl-4- (6'-aminonaphthalene-2
3.95 g of -yl) aniline (Compound of Exemplified Compound 1) was obtained as pale yellow crystals.
【０１００】実施例２：例示化合物３の製造
実施例１のＮ，Ｎ−ジフェニル−６−ブロモ−２−ナ
フチルアミンの製造において、ヨウ化ベンゼン５０ｇを
使用する代わりに、２−ヨードナフタレン６２．３ｇを
使用した以外は、実施例１のに記載の操作に従い、Ｎ
−フェニル−Ｎ−（２’−ナフチル）−６−ブロモ−２
−ナフチルアミンを製造した。次ぎに、実施例１のに
おいて、Ｎ，Ｎ−ジフェニル−６−ブロモ−２−ナフチ
ルアミンを１８．７ｇ使用する代わりにＮ−フェニル−
Ｎ−（２’−ナフチル）−６−ブロモ−２−ナフチルア
ミンを２１．２ｇ使用した以外は、実施例１のに記載
の操作に従いＮ−フェニル−Ｎ−（２’−ナフチル）−
２−アミノ−６−ナフチルボロン酸を製造した、次ぎ
に、実施例１のにおいて、Ｎ，Ｎ−ジフェニル−４−
ヨードアニリン３．７１ｇおよび、Ｎ，Ｎ−ジフェニル
−２−アミノ−６−ナフタレンボロン酸３．３９ｇを使
用する代わりに、Ｎ−フェニル−Ｎ−（２’−ナフチ
ル）−４−ヨードアニリン４．２１ｇおよびＮ−フェニ
ル−Ｎ−（２’−ナフチル）−２−アミノ−６−ナフタ
レンボロン酸３．８９ｇを使用した以外は、実施例１の
に記載の操作に従い、例示化合物３を淡黄色結晶とし
て４．２９ｇ得た。Example 2: Preparation of Exemplified Compound 3 In the preparation of N, N-diphenyl-6-bromo-2-naphthylamine of Example 1, instead of using 50 g of iodobenzene, 62.3 g of 2-iodonaphthalene was used. According to the procedure described in Example 1, except that
-Phenyl-N- (2'-naphthyl) -6-bromo-2
-Naphthylamine was prepared. Next, in Example 1, instead of using 18.7 g of N, N-diphenyl-6-bromo-2-naphthylamine, N-phenyl-
N-Phenyl-N- (2'-naphthyl)-according to the procedure described in Example 1 except that 21.2 g of N- (2'-naphthyl) -6-bromo-2-naphthylamine was used.
2-Amino-6-naphthylboronic acid was prepared, then in Example 1, N, N-diphenyl-4-
3. Instead of using 3.71 g of iodoaniline and 3.39 g of N, N-diphenyl-2-amino-6-naphthaleneboronic acid, N-phenyl-N- (2'-naphthyl) -4-iodoaniline 4. 21 g and N-phenyl-N- (2′-naphthyl) -2-amino-6-naphthaleneboronic acid (3.89 g) were used according to the procedure described in Example 1, except that pale yellow crystals of Compound 3 were used. As a result, 4.29 g was obtained.
【０１０１】実施例３：例示化合物９の製造
実施例１のＮ，Ｎ−ジフェニル−６−ブロモ−２−ナ
フチルアミンの製造において、ヨウ化ベンゼン５０ｇを
使用する代わりに、４−フェニル−ヨウ化ベンゼン６７
ｇを使用した以外は、実施例１のに記載の操作に従
い、Ｎ−フェニル−Ｎ−（４’−フェニルフェニル）−
６−ブロモ−２−ナフチルアミンを製造した。次ぎに、
実施例１のにおいて、Ｎ，Ｎ−ジフェニル−６−ブロ
モ−２−ナフチルアミンを１８．７ｇ使用する代わりに
Ｎ−フェニル−（４’−フェニルフェニル）−６−ブロ
モ−２−ナフチルアミンを２２．５ｇ使用した以外は、
実施例１のに記載の操作に従いＮ−フェニル−Ｎ−
（４’−フェニルフェニル）−２−アミノ−６−ナフチ
ルボロン酸を製造した、次ぎに、実施例１のにおい
て、Ｎ，Ｎ−ジフェニル−４−ヨードアニリン３．７１
ｇおよび、Ｎ，Ｎ−ジフェニル−２−アミノ−６−ナフ
タレンボロン酸３．３９ｇを使用する代わりに、Ｎ−フ
ェニル−Ｎ−（４’−フェニルフェニル）−４−ブロモ
アニリン４．００ｇおよびＮ−フェニル−Ｎ−（４’−
フェニルフェニル）−２−アミノ−６−ナフタレンボロ
ン酸４．１５ｇを使用した以外は、実施例１のに記載
の操作に従い、例示化合物９を淡黄色結晶として５．０
２ｇ得た。Example 3: Preparation of Exemplified Compound 9 In the preparation of N, N-diphenyl-6-bromo-2-naphthylamine of Example 1, instead of using 50 g of iodobenzene, 4-phenyl-iodobenzene was used. 67
N-phenyl-N- (4'-phenylphenyl)-was prepared according to the procedure described in Example 1 except that g was used.
6-Bromo-2-naphthylamine was prepared. Next,
In Example 1, instead of using 18.7 g of N, N-diphenyl-6-bromo-2-naphthylamine, 22.5 g of N-phenyl- (4′-phenylphenyl) -6-bromo-2-naphthylamine was used. Except that I used
According to the procedure described in Example 1, N-phenyl-N-
(4'-Phenylphenyl) -2-amino-6-naphthylboronic acid was prepared, then in Example 1, N, N-diphenyl-4-iodoaniline 3.71.
g and N, N-diphenyl-2-amino-6-naphthaleneboronic acid 3.39 g instead of using N-phenyl-N- (4′-phenylphenyl) -4-bromoaniline 4.00 g and N -Phenyl-N- (4'-
Phenylphenyl) -2-amino-6-naphthaleneboronic acid was used according to the procedure described in Example 1, except that 4.15 g of Exemplified Compound 9 was used as pale yellow crystals to give 5.0.
2 g was obtained.
【０１０２】実施例４：例示化合物１６の製造
実施例１のにおいて、Ｎ，Ｎ−ジフェニル−４−ヨー
ドアニリン３．７１ｇおよび、Ｎ，Ｎ−ジフェニル−２
−アミノ−６−ナフタレンボロン酸３．３９ｇを使用す
る代わりに、Ｎ−フェニル−Ｎ−（４’−フェニルフェ
ニル）−４−ブロモアニリン４．００ｇおよびＮ−フェ
ニル−Ｎ−（１’−ナフチル）−２−アミノ−６−ナフ
タレンボロン酸３．８９ｇを使用した以外は、実施例１
のに記載の操作に従い、例示化合物１６を淡黄色結晶
として４．５６ｇ得た。Example 4: Preparation of Exemplified Compound 16 In Example 1, 3.71 g of N, N-diphenyl-4-iodoaniline and N, N-diphenyl-2 were used.
Instead of using 3.39 g of -amino-6-naphthaleneboronic acid, 4.00 g of N-phenyl-N- (4'-phenylphenyl) -4-bromoaniline and N-phenyl-N- (1'-naphthyl) ) -2-Amino-6-naphthaleneboronic acid Example 1 except that 3.89 g was used.
According to the operation described in, 4.56 g of Exemplified Compound 16 was obtained as pale yellow crystals.
【０１０３】実施例５：例示化合物３６の製造
実施例１のにおいて、Ｎ，Ｎ−ジフェニル−２−アミ
ノ−６−ナフタレンボロン酸３．３９ｇを使用する代わ
りに、Ｎ−フェニル−Ｎ−（１’−ナフチル）−２−ア
ミノ−６−ナフタレンボロン酸３．８９ｇを使用した以
外は、実施例１のに記載の操作に従い、例示化合物３
６を淡黄色結晶として３．７８ｇ得た。Example 5: Preparation of Exemplified Compound 36 Instead of using 3.39 g of N, N-diphenyl-2-amino-6-naphthaleneboronic acid in Example 1, N-phenyl-N- (1 According to the procedure described in Example 1, except that 3.89 g of'-naphthyl) -2-amino-6-naphthaleneboronic acid was used, Exemplified Compound 3
3.78 g of 6 was obtained as pale yellow crystals.
【０１０４】実施例６：例示化合物３７の製造
実施例１のにおいて、Ｎ，Ｎ−ジフェニル−４−ヨー
ドアニリン３．７１ｇを使用する代わりに、Ｎ−フェニ
ル−Ｎ−（１’−ピレニル）−４−ヨードアニリン４．
９５ｇを使用した以外は、実施例１のに記載の操作に
従い、例示化合物３７を淡黄色結晶として４．３１ｇ得
た。Example 6: Preparation of Exemplified Compound 37 Instead of using 3.71 g of N, N-diphenyl-4-iodoaniline in Example 1, N-phenyl-N- (1'-pyrenyl)- 4-Iodoaniline 4.
According to the procedure described in Example 1, except that 95 g was used, 4.31 g of Exemplified Compound 37 was obtained as pale yellow crystals.
【０１０５】実施例７：例示化合物３８の製造
実施例１のにおいて、Ｎ，Ｎ−ジフェニル−４−ヨー
ドアニリン３．７１ｇを使用する代わりに、Ｎ−フェニ
ル−Ｎ−（１’−ナフチル）−４−ブロモアニリン４．
２１ｇを使用した以外は、実施例１のに記載の操作に
従い、例示化合物３８を淡黄色結晶として３．６４ｇ得
た。Example 7: Preparation of Exemplified Compound 38 Instead of using 3.71 g of N, N-diphenyl-4-iodoaniline in Example 1, N-phenyl-N- (1'-naphthyl)- 4-bromoaniline 4.
According to the procedure described in Example 1, except that 21 g was used, 3.64 g of Exemplified Compound 38 was obtained as pale yellow crystals.
【０１０６】実施例８：例示化合物４２の製造
実施例１のにおいて、Ｎ，Ｎ−ジフェニル−４−ヨー
ドアニリン３．７１ｇおよび、Ｎ，Ｎ−ジフェニル−２
−アミノ−６−ナフタレンボロン酸３．３９ｇを使用す
る代わりに、Ｎ−フェニル−Ｎ−（１’−ピレニル）−
４−ブロモアニリン４．４８ｇおよびＮ−フェニル−Ｎ
−（２’−ナフチル）−２−アミノ−６−ナフタレンボ
ロン酸３．８９ｇを使用した以外は、実施例１のに記
載の操作に従い、例示化合物４２を淡黄色結晶として
４．０５ｇ得た。Example 8: Production of Exemplified Compound 42 In Example 1, 3.71 g of N, N-diphenyl-4-iodoaniline and N, N-diphenyl-2 were used.
Instead of using 3.39 g of -amino-6-naphthaleneboronic acid, N-phenyl-N- (1'-pyrenyl)-
4-Bromoaniline 4.48 g and N-phenyl-N
Except that 3.89 g of-(2'-naphthyl) -2-amino-6-naphthaleneboronic acid was used, 4.05 g of Exemplified Compound 42 was obtained as pale yellow crystals according to the procedure described in Example 1.
【０１０７】実施例９：例示化合物４３の製造
実施例１のにおいて、Ｎ，Ｎ−ジフェニル−４−ヨー
ドアニリン３．７１ｇおよび、Ｎ，Ｎ−ジフェニル−２
−アミノ−６−ナフタレンボロン酸３．３９ｇを使用す
る代わりに、Ｎ−フェニル−Ｎ−（１’−ピレニル）−
４−ブロモアニリン４．４８ｇおよびＮ−フェニル−Ｎ
−（４’−フェニルフェニル）−２−アミノ−６−ナフ
タレンボロン酸４．１５ｇを使用した以外は、実施例１
のに記載の操作に従い、例示化合物４３を淡黄色結晶
として５．１０ｇ得た。Example 9: Production of Exemplified Compound 43 In Example 1, 3.71 g of N, N-diphenyl-4-iodoaniline and N, N-diphenyl-2 were used.
Instead of using 3.39 g of -amino-6-naphthaleneboronic acid, N-phenyl-N- (1'-pyrenyl)-
4-Bromoaniline 4.48 g and N-phenyl-N
Example 1 except that 4.15 g of-(4'-phenylphenyl) -2-amino-6-naphthaleneboronic acid was used.
According to the operation described in, 5.10 g of Exemplified Compound 43 was obtained as pale yellow crystals.
【０１０８】実施例１０：例示化合物４４の製造
実施例１のにおいて、Ｎ，Ｎ−ジフェニル−２−アミ
ノ−６−ナフタレンボロン酸３．３９ｇを使用する代わ
りに、Ｎ−フェニル−Ｎ−（４’−フェニルフェニル）
−２−アミノ−６−ナフタレンボロン酸４．１５ｇを使
用した以外は、実施例１のに記載の操作に従い、例示
化合物４４を淡黄色結晶として４．７５ｇ得た。Example 10: Preparation of Exemplified Compound 44 Instead of using 3.39 g of N, N-diphenyl-2-amino-6-naphthaleneboronic acid in Example 1, N-phenyl-N- (4 '-Phenylphenyl)
Following the procedure described in Example 1, except that 4.15 g of 2-amino-6-naphthaleneboronic acid was used, 4.75 g of Exemplified Compound 44 was obtained as pale yellow crystals.
【０１０９】実施例１１：有機電界発光素子の作製
厚さ２００ｎｍのＩＴＯ透明電極（陽極）を有するガラ
ス基板を、中性洗剤、セミコクリーン（フルウチ化学
製）、超純水、アセトン、エタノールを用いて超音波洗
浄した。この基板を窒素ガスを用いて乾燥し、さらにＵ
Ｖ／オゾン洗浄した後、蒸着装置の基板ホルダーに固定
し、蒸着槽を３×１０-6Torrに減圧した。先ず、ＩＴＯ
透明電極上に、例示化合物１の化合物を蒸着速度０．２
ｎｍ／ｓｅｃで７５ｎｍの厚さに蒸着し、正孔注入輸送
層を形成した。次に、正孔注入輸送層の上にトリス（８
−キノリノラート）アルミニウムを蒸着速度０．２ｎｍ
／ｓｅｃで５０ｎｍの厚さに蒸着し、電子注入輸送層を
兼ね備えた発光層を形成した。さらに、その上に、陰極
としてマグネシウムと銀を蒸着速度０．２ｎｍ／ｓｅｃ
で２００ｎｍの厚さに共蒸着（重量比１０：１）して陰
極とし、有機電界発光素子を作製した。尚、蒸着は、蒸
着槽の減圧状態を保ったまま実施した。作製した有機電
界発光素子に直流電圧を印加し、５０℃、乾燥雰囲気
下、１０ｍＡ／ｃｍ2の定電流密度で連続駆動させた。
初期には、６．０Ｖ、輝度４８０ｃｄ／ｍ2の緑色の発
光が確認された。輝度の半減期は６３０時間であった。Example 11: Preparation of organic electroluminescent device A glass substrate having a 200 nm thick ITO transparent electrode (anode) was prepared by using a neutral detergent, semicoclean (manufactured by Furuuchi Chemical Co., Ltd.), ultrapure water, acetone and ethanol. And ultrasonically cleaned. This substrate is dried using nitrogen gas, and further U
After V / ozone cleaning, the substrate was fixed to a substrate holder of a vapor deposition device, and the vapor deposition tank was depressurized to 3 × 10 −6 Torr. First, ITO
The compound of Exemplified Compound 1 was deposited on the transparent electrode at a deposition rate of 0.2.
The hole injecting and transporting layer was formed by vapor deposition to a thickness of 75 nm at nm / sec. Next, on the hole injecting and transporting layer, tris (8
-Quinolinolato) aluminum vapor deposition rate 0.2 nm
/ Sec to a thickness of 50 nm to form a light emitting layer which also serves as an electron injecting and transporting layer. Furthermore, magnesium and silver as a cathode are vapor-deposited thereon with a deposition rate of 0.2 nm / sec.
Was co-evaporated to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. A direct current voltage was applied to the produced organic electroluminescence device, and it was continuously driven at a constant current density of 10 mA / cm 2 in a dry atmosphere at 50 ° C.
Initially, green light emission of 6.0 V and a luminance of 480 cd / m 2 was confirmed. The half-life of brightness was 630 hours.
【０１１０】実施例１２〜１９：有機電界発光素子の作
製
実施例１１において、正孔注入輸送層の形成に際して、
例示化合物１の化合物を使用する代わりに、例示化合物
３の化合物（実施例１２）、例示化合物９の化合物（実
施例１３）、例示化合物１６の化合物（実施例１４）、
例示化合物３６の化合物（実施例１５）、例示化合物３
７の化合物（実施例１６）、例示化合物３８の化合物
（実施例１７）、例示化合物４２の化合物（実施例１
８）、例示化合物４３の化合物（実施例１９）を使用し
た以外は、実施例１１に記載の操作に従い、有機電界発
光素子を作製した。各素子からは緑色の発光が確認され
た。さらにその特性を調べ、結果を（第１表）（表１）
に示した。Examples 12 to 19: Preparation of organic electroluminescent device In Example 11, in forming the hole injecting and transporting layer,
Instead of using the compound of Exemplified Compound 1, the compound of Exemplified Compound 3 (Example 12), the compound of Exemplified Compound 9 (Example 13), the compound of Exemplified Compound 16 (Example 14),
Compound of Exemplified Compound 36 (Example 15), Exemplified Compound 3
7 compound (Example 16), exemplified compound 38 compound (Example 17), exemplified compound 42 compound (Example 1)
8), an organic electroluminescent device was produced according to the procedure described in Example 11 except that the compound of Exemplified Compound 43 (Example 19) was used. Green light emission was confirmed from each element. Furthermore, the characteristics were examined, and the results (Table 1) (Table 1)
It was shown to.
【０１１１】比較例１：実施例１１において、正孔注入
輸送層の形成に際して、例示化合物１の化合物を使用す
る代わりに、４，４’−ビス〔Ｎ−フェニル−Ｎ−
（３”−メチルフェニル）アミノ〕ビフェニルを使用し
た以外は実施例１１に記載の操作に従い、有機電界発光
素子を作製した。素子からは緑色の発光が確認された。
さらにその特性を調べ、結果を（第１表）（表１）に示
した。Comparative Example 1: In Example 11, instead of using the compound of Exemplified Compound 1 in the formation of the hole injecting and transporting layer, 4,4'-bis [N-phenyl-N-
An organic electroluminescent device was produced by following the procedure described in Example 11 except that (3 ″ -methylphenyl) amino] biphenyl was used. Green luminescence was confirmed from the device.
Further, its characteristics were examined, and the results are shown in (Table 1) (Table 1).
【０１１２】比較例２：実施例１１において、正孔注入
輸送層の形成に際して、例示化合物１の化合物を使用す
る代わりに、９，９−ジメチル−２，７−ビス（Ｎ，Ｎ
−ジフェニルアミノ）フルオレンを使用した以外は実施
例１１に記載の操作に従い、有機電界発光素子を作製し
た。各素子からは緑色の発光が確認された。さらにその
特性を調べ、結果を（第１表）（表１）に示した。Comparative Example 2: In Example 11, instead of using the compound of Exemplified Compound 1 in the formation of the hole injecting and transporting layer, 9,9-dimethyl-2,7-bis (N, N) was used.
An organic electroluminescent device was produced by following the procedure described in Example 11 except that -diphenylamino) fluorene was used. Green light emission was confirmed from each element. Further, its characteristics were examined, and the results are shown in (Table 1) (Table 1).
【０１１３】[0113]
【表１】 [Table 1]
【０１１４】実施例２０：有機電界発光素子の作製
厚さ２００ｎｍのＩＴＯ透明電極（陽極）を有するガラ
ス基板を、中性洗剤、セミコクリーン（フルウチ化学
製）、超純水、アセトン、エタノールを用いて超音波洗
浄した。この基板を窒素ガスを用いて乾燥し、さらにＵ
Ｖ／オゾン洗浄した後、蒸着装置の基板ホルダーに固定
し、蒸着槽を３×１０-6Torrに減圧した。先ず、ＩＴＯ
透明電極上に、ポリ（チオフェン−２，５−ジイル）を
蒸着速度０．１ｎｍ／secで、２０ｎｍの厚さに蒸着
し、第１正孔注入輸送層を形成した。次いで、例示化合
物１６の化合物を蒸着速度０．２ｎｍ／ｓｅｃで５５ｎ
ｍの厚さに蒸着し、第２正孔注入輸送層を形成した。次
に、正孔注入輸送層の上にトリス（８−キノリノラー
ト）アルミニウムを蒸着速度０．２ｎｍ／ｓｅｃで５０
ｎｍの厚さに蒸着し、電子注入輸送層を兼ね備えた発光
層を形成した。さらに、その上に、陰極としてマグネシ
ウムと銀を蒸着速度０．２ｎｍ／ｓｅｃで２００ｎｍの
厚さに共蒸着（重量比１０：１）して陰極とし、有機電
界発光素子を作製した。尚、蒸着は、蒸着槽の減圧状態
を保ったまま実施した。作製した有機電界発光素子に直
流電圧を印加し、乾燥雰囲気下、１０ｍＡ／ｃｍ2の定
電流密度で連続駆動させた。初期には、６．１Ｖ、輝度
５００ｃｄ／ｍ2の緑色の発光が確認された。輝度の半
減期は１６００時間であった。Example 20: Preparation of organic electroluminescent device A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was treated with a neutral detergent, semicoclean (Furuuchi Chemical Co., Ltd.), ultrapure water, acetone, and ethanol. And ultrasonically cleaned. This substrate is dried using nitrogen gas, and further U
After V / ozone cleaning, the substrate was fixed to a substrate holder of a vapor deposition device, and the vapor deposition tank was depressurized to 3 × 10 −6 Torr. First, ITO
Poly (thiophene-2,5-diyl) was deposited on the transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole injecting and transporting layer. Then, the compound of Exemplified Compound 16 was deposited at a deposition rate of 0.2 nm / sec to 55 n.
The second hole injecting and transporting layer was formed by vapor deposition to a thickness of m. Next, tris (8-quinolinolato) aluminum is deposited on the hole injecting and transporting layer at a deposition rate of 0.2 nm / sec.
It was vapor-deposited to a thickness of nm to form a light emitting layer which also serves as an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. A direct current voltage was applied to the produced organic electroluminescent device, and it was continuously driven at a constant current density of 10 mA / cm 2 in a dry atmosphere. Initially, green light emission of 6.1 V and a luminance of 500 cd / m 2 was confirmed. The half-life of brightness was 1600 hours.
【０１１５】実施例２１：有機電界発光素子の作製
厚さ２００ｎｍのＩＴＯ透明電極（陽極）を有するガラ
ス基板を、中性洗剤、セミコクリーン（フルウチ化学
製）、超純水、アセトン、エタノールを用いて超音波洗
浄した。この基板を窒素ガスを用いて乾燥し、さらにＵ
Ｖ／オゾン洗浄した後、蒸着装置の基板ホルダーに固定
し、蒸着槽を３×１０-6Torrに減圧した。先ず、ＩＴＯ
透明電極上に、４，４’，４”−トリス〔Ｎ−（３”−
メチルフェニル）−Ｎ−フェニルアミノ〕トリフェニル
アミンを蒸着速度０．１ｎｍ／ｓｅｃで、５０ｎｍの厚
さに蒸着し、第１正孔注入輸送層を形成した。次いで、
例示化合物３の化合物とルブレンを、異なる蒸着源か
ら、蒸着速度０．２ｎｍ／ｓｅｃで２０ｎｍの厚さに共
蒸着（重量比１０：１）し、第２正孔注入輸送層を兼ね
備えた発光層を形成した。次いで、その上にトリス（８
−キノリノラート）アルミニウムを蒸着速度０．２ｎｍ
／ｓｅｃで５０ｎｍの厚さに蒸着し、電子注入輸送層を
兼ね備えた発光層を形成した。さらに、その上に、陰極
としてマグネシウムと銀を蒸着速度０．２ｎｍ／ｓｅｃ
で２００ｎｍの厚さに共蒸着（重量比１０：１）して陰
極とし、有機電界発光素子を作製した。作製した有機電
界発光素子に直流電圧を印加し、乾燥雰囲気下、１０ｍ
Ａ／ｃｍ2の定電流密度で連続駆動させた。初期には、
６．０Ｖ、輝度４８０ｃｄ／ｍ2の黄色の発光が確認さ
れた。輝度の半減期は１６００時間であった。Example 21: Preparation of organic electroluminescent element A glass substrate having a 200 nm thick ITO transparent electrode (anode) was used with a neutral detergent, semicoclean (manufactured by Furuuchi Chemical Co., Ltd.), ultrapure water, acetone, and ethanol. And ultrasonically cleaned. This substrate is dried using nitrogen gas, and further U
After V / ozone cleaning, the substrate was fixed to a substrate holder of a vapor deposition device, and the vapor deposition tank was depressurized to 3 × 10 −6 Torr. First, ITO
On the transparent electrode, 4,4 ', 4 "-tris [N- (3"-
Methylphenyl) -N-phenylamino] triphenylamine was deposited at a deposition rate of 0.1 nm / sec to a thickness of 50 nm to form a first hole injecting and transporting layer. Then
The compound of Exemplified Compound 3 and rubrene were co-evaporated from different vapor deposition sources at a vapor deposition rate of 0.2 nm / sec to a thickness of 20 nm (weight ratio 10: 1) to form a light emitting layer also serving as a second hole injecting and transporting layer. Was formed. Then add Tris (8
-Quinolinolato) aluminum vapor deposition rate 0.2 nm
/ Sec to a thickness of 50 nm to form a light emitting layer which also serves as an electron injecting and transporting layer. Furthermore, magnesium and silver as a cathode are vapor-deposited thereon with a deposition rate of 0.2 nm / sec.
Was co-evaporated to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. A direct current voltage is applied to the produced organic electroluminescent device in a dry atmosphere for 10 m.
It was continuously driven at a constant current density of A / cm 2 . In the early days,
Yellow emission at 6.0 V and a luminance of 480 cd / m 2 was confirmed. The half-life of brightness was 1600 hours.
【０１１６】実施例２２：有機電界発光素子の作製
厚さ２００ｎｍのＩＴＯ透明電極（陽極）を有するガラ
ス基板を、中性洗剤、セミコクリーン（フルウチ化学
製）、超純水、アセトン、エタノールを用いて超音波洗
浄した。この基板を窒素ガスを用いて乾燥し、さらにＵ
Ｖ／オゾン洗浄した後、蒸着装置の基板ホルダーに固定
し、蒸着槽を３×１０-6Torrに減圧した。先ず、ＩＴＯ
透明電極上に、ポリ（チオフェン−２，５−ジイル）を
蒸着速度０．１ｎｍ／secで、２０ｎｍの厚さに蒸着
し、第１正孔注入輸送層を形成した。蒸着槽を大気圧下
に戻した後、再び蒸着槽を３×１０-6Torrに減圧した。
次いで、例示化合物３８の化合物とルブレンを、異なる
蒸着源から、蒸着速度０．２ｎｍ／ｓｅｃで５５ｎｍの
厚さに共蒸着（重量比１０：１）し、第２正孔注入輸送
層を兼ね備えた発光層を形成した。減圧状態を保ったま
ま、次に、その上にトリス（８−キノリノラート）アル
ミニウムを蒸着速度０．２ｎｍ／ｓｅｃで５０ｎｍの厚
さに蒸着し、電子注入輸送層を形成した。減圧状態を保
ったまま、さらに、その上に、陰極としてマグネシウム
と銀を蒸着速度０．２ｎｍ／ｓｅｃで２００ｎｍの厚さ
に共蒸着（重量比１０：１）して陰極とし、有機電界発
光素子を作製した。作製した有機電界発光素子に直流電
圧を印加し、乾燥雰囲気下、１０ｍＡ／ｃｍ2の定電流
密度で連続駆動させた。初期には、６．２Ｖ、輝度４７
０ｃｄ／ｍ2の黄色の発光が確認された。輝度の半減期
は１５００時間であった。Example 22: Preparation of organic electroluminescent device A glass substrate having a 200 nm thick ITO transparent electrode (anode) was prepared using neutral detergent, semicoclean (Furuuchi Chemical Co., Ltd.), ultrapure water, acetone and ethanol. And ultrasonically cleaned. This substrate is dried using nitrogen gas, and further U
After V / ozone cleaning, the substrate was fixed to a substrate holder of a vapor deposition device, and the vapor deposition tank was depressurized to 3 × 10 −6 Torr. First, ITO
Poly (thiophene-2,5-diyl) was deposited on the transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole injecting and transporting layer. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was depressurized again to 3 × 10 −6 Torr.
Then, the compound of Exemplified Compound 38 and rubrene were co-evaporated from different vapor deposition sources at a vapor deposition rate of 0.2 nm / sec to a thickness of 55 nm (weight ratio 10: 1) to serve also as a second hole injecting and transporting layer. A light emitting layer was formed. While maintaining the reduced pressure, tris (8-quinolinolato) aluminum was then vapor-deposited thereon at a vapor deposition rate of 0.2 nm / sec. To a thickness of 50 nm to form an electron injecting and transporting layer. While maintaining the reduced pressure state, magnesium and silver were co-deposited as a cathode at a vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, which was used as an organic electroluminescence device. Was produced. A direct current voltage was applied to the produced organic electroluminescent device, and it was continuously driven at a constant current density of 10 mA / cm 2 in a dry atmosphere. Initially, 6.2V, brightness 47
A yellow emission of 0 cd / m 2 was confirmed. The half-life of brightness was 1500 hours.
【０１１７】実施例２３：有機電界発光素子の作製
厚さ２００ｎｍのＩＴＯ透明電極（陽極）を有するガラ
ス基板を、中性洗剤、セミコクリーン（フルウチ化学
製）、超純水、アセトン、エタノールを用いて超音波洗
浄した。この基板を窒素ガスを用いて乾燥し、さらにＵ
Ｖ／オゾン洗浄した後、蒸着装置の基板ホルダーに固定
し、蒸着槽を３×１０-6Torrに減圧した。先ず、ＩＴＯ
透明電極上に、例示化合物９を蒸着速度０．１ｎｍ／se
cで、２０ｎｍの厚さに蒸着し、第１正孔注入輸送層を
形成した。蒸着槽を大気圧下に戻した後、再び蒸着槽を
３×１０-6Torrに減圧した。次いで、例示化合物４４の
化合物とルブレンを、異なる蒸着源から、蒸着速度０．
２ｎｍ／ｓｅｃで５５ｎｍの厚さに共蒸着（重量比１
０：１）し、第２正孔注入輸送層を兼ね備えた発光層を
形成した。次に、その上にトリス（８−キノリノラー
ト）アルミニウムを蒸着速度０．２ｎｍ／ｓｅｃで５０
ｎｍの厚さに蒸着し、電子注入輸送層を形成した。さら
に、その上に、陰極としてマグネシウムと銀を蒸着速度
０．２ｎｍ／ｓｅｃで２００ｎｍの厚さに共蒸着（重量
比１０：１）して陰極とし、有機電界発光素子を作製し
た。尚、蒸着は、蒸着槽の減圧状態を保ったまま実施し
た。作製した有機電界発光素子に直流電圧印加し、乾燥
雰囲気下、１０ｍＡ／ｃｍ2の定電流密度で連続駆動さ
せた。初期には、６．１Ｖ、輝度５４０ｃｄ／ｍ2の黄
色の発光が確認された。輝度の半減期は１７５０時間で
あった。Example 23: Preparation of organic electroluminescent device A glass substrate having a 200 nm thick ITO transparent electrode (anode) was prepared using neutral detergent, semicoclean (Furuuchi Chemical Co., Ltd.), ultrapure water, acetone and ethanol. And ultrasonically cleaned. This substrate is dried using nitrogen gas, and further U
After V / ozone cleaning, the substrate was fixed to a substrate holder of a vapor deposition device, and the vapor deposition tank was depressurized to 3 × 10 −6 Torr. First, ITO
Exemplified Compound 9 was deposited on the transparent electrode at a deposition rate of 0.1 nm / se.
In step c, vapor deposition was performed to a thickness of 20 nm to form a first hole injecting and transporting layer. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was depressurized again to 3 × 10 −6 Torr. Then, the compound of Exemplified Compound 44 and rubrene were evaporated from different evaporation sources at a deposition rate of 0.
Co-deposited to a thickness of 55 nm at 2 nm / sec (weight ratio 1
0: 1) to form a light emitting layer which also serves as a second hole injecting and transporting layer. Then, tris (8-quinolinolato) aluminum is deposited thereon at a deposition rate of 0.2 nm / sec.
It was vapor-deposited to a thickness of nm to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. A direct current voltage was applied to the produced organic electroluminescence device, and it was continuously driven at a constant current density of 10 mA / cm 2 in a dry atmosphere. In the initial stage, yellow light emission of 6.1 V and a luminance of 540 cd / m 2 was confirmed. The half-life of brightness was 1750 hours.
【０１１８】実施例２４：有機電界発光素子の作製
厚さ２００ｎｍのＩＴＯ透明電極（陽極）を有するガラ
ス基板を、中性洗剤、セミコクリーン（フルウチ化学
製）、超純水、アセトン、エタノールを用いて超音波洗
浄した。この基板を窒素ガスを用いて乾燥し、さらにＵ
Ｖ／オゾン洗浄した。次に、ＩＴＯ透明電極上に、ポリ
カーボネート（重量平均分子量３９０００）と例示化合
物１６の化合物を重量比１００：５０の割合で含有する
３重量％ジクロロエタン溶液を用いてスピンコート法に
より、４０ｎｍの正孔注入輸送層を形成した。次にこの
正孔注入輸送層を有するガラス基板を、蒸着装置の基板
ホルダーに固定し、蒸着層を３×１０-6Torrに減圧し
た。次に、その上にトリス（８−キノリノラート）アル
ミニウムを蒸着速度０．２ｎｍ／ｓｅｃで５０ｎｍの厚
さに蒸着し、電子注入輸送層を兼ね備えた発光層を形成
した。さらに、その上に、陰極としてマグネシウムと銀
を蒸着速度０．２ｎｍ／ｓｅｃで２００ｎｍの厚さに共
蒸着（重量比１０：１）して陰極とし、有機電界発光素
子を作製した。作製した有機電界発光素子に乾燥雰囲気
下、１０Ｖの直流電圧を印加したところ、８９ｍＡ／ｃ
ｍ2の電流が流れた。輝度９８０ｃｄ／ｍ2の緑色の発光
が確認された。輝度の半減期は３５０時間であった。Example 24: Preparation of organic electroluminescent device A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was used with neutral detergent, semicoclean (Furuuchi Chemical Co., Ltd.), ultrapure water, acetone, and ethanol. And ultrasonically cleaned. This substrate is dried using nitrogen gas, and further U
V / ozone cleaning was performed. Next, by using a 3 wt% dichloroethane solution containing polycarbonate (weight average molecular weight 39000) and the compound of Exemplified Compound 16 in a weight ratio of 100: 50 on the ITO transparent electrode, a hole of 40 nm was formed by spin coating. An injection transport layer was formed. Next, the glass substrate having the hole injecting and transporting layer was fixed to a substrate holder of a vapor deposition device, and the vapor deposition layer was depressurized to 3 × 10 −6 Torr. Next, tris (8-quinolinolato) aluminum was vapor-deposited thereon at a vapor deposition rate of 0.2 nm / sec. To a thickness of 50 nm to form a light-emitting layer also serving as an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. When a direct current voltage of 10 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 89 mA / c.
An electric current of m 2 flowed. Green light emission with a brightness of 980 cd / m 2 was confirmed. The half-life of brightness was 350 hours.
【０１１９】実施例２５：有機電界発光素子の作製
厚さ２００ｎｍのＩＴＯ透明電極（陽極）を有するガラ
ス基板を、中性洗剤、セミコクリーン（フルウチ化学
製）、超純水、アセトン、エタノールを用いて超音波洗
浄した。この基板を窒素ガスを用いて乾燥し、さらにＵ
Ｖ／オゾン洗浄した。次に、ＩＴＯ透明電極上に、ポリ
メチルメタクリレート（重量平均分子量２５０００）、
例示化合物４２の化合物、トリス（８−キノリノラー
ト）アルミニウムをそれぞれ重量比１００：５０：０．
５の割合で含有する３重量％ジクロロエタン溶液を用い
てスピンコート法により、１００ｎｍの発光層を形成し
た。次にこの発光層を有するガラス基板を、蒸着装置の
基板ホルダーに固定し、蒸着層を３×１０-6Torrに減圧
した。発光層の上に、陰極としてマグネシウムと銀を蒸
着速度０．２ｎｍ／ｓｅｃで２００ｎｍの厚さに共蒸着
（重量比１０：１）して陰極とし、有機電界発光素子を
作製した。作製した有機電界発光素子に乾燥雰囲気下、
１５Ｖの直流電圧を印加したところ、８６ｍＡ／ｃｍ2
の電流が流れた。輝度５６０ｃｄ／ｍ2の緑色の発光が
確認された。輝度の半減期は５００時間であった。Example 25: Preparation of organic electroluminescent device A glass substrate having a 200 nm thick ITO transparent electrode (anode) was prepared using neutral detergent, semicoclean (Furuuchi Chemical Co., Ltd.), ultrapure water, acetone and ethanol. And ultrasonically cleaned. This substrate is dried using nitrogen gas, and further U
V / ozone cleaning was performed. Next, on the ITO transparent electrode, polymethylmethacrylate (weight average molecular weight 25,000),
The compound of Exemplified Compound 42 and tris (8-quinolinolato) aluminum were mixed in a weight ratio of 100: 50: 0.
A 100-nm light emitting layer was formed by a spin coating method using a 3 wt% dichloroethane solution contained in a ratio of 5. Next, the glass substrate having this light emitting layer was fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition layer was depressurized to 3 × 10 −6 Torr. On the light emitting layer, magnesium and silver were co-deposited as a cathode at a vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to serve as a cathode, and an organic electroluminescence device was produced. In the prepared organic electroluminescent device in a dry atmosphere,
When a DC voltage of 15 V was applied, 86 mA / cm 2
Current flowed. Green light emission with a luminance of 560 cd / m 2 was confirmed. The half-life of brightness was 500 hours.
【０１２０】[0120]
【発明の効果】本発明により、新規なアミン化合物、お
よび発光寿命が長く、耐久性に優れた有機電界発光素子
を提供することが可能になった。Industrial Applicability According to the present invention, it is possible to provide a novel amine compound and an organic electroluminescent device having a long emission life and excellent durability.
【図１】有機電界発光素子の一例の断面概略図である。FIG. 1 is a schematic cross-sectional view of an example of an organic electroluminescent device.
【図２】有機電界発光素子の一例の断面概略図である。FIG. 2 is a schematic cross-sectional view of an example of an organic electroluminescent device.
【図３】有機電界発光素子の一例の断面概略図である。FIG. 3 is a schematic cross-sectional view of an example of an organic electroluminescent device.
【図４】有機電界発光素子の一例の断面概略図である。FIG. 4 is a schematic cross-sectional view of an example of an organic electroluminescent device.
【図５】有機電界発光素子の一例の断面概略図である。FIG. 5 is a schematic cross-sectional view of an example of an organic electroluminescent device.
【図６】有機電界発光素子の一例の断面概略図である。FIG. 6 is a schematic cross-sectional view of an example of an organic electroluminescent device.
【図７】有機電界発光素子の一例の断面概略図である。FIG. 7 is a schematic cross-sectional view of an example of an organic electroluminescent device.
【図８】有機電界発光素子の一例の断面概略図である。FIG. 8 is a schematic cross-sectional view of an example of an organic electroluminescent device.
１：基板 ２：陽極 ３：正孔注入輸送層 ３ａ：正孔注入輸送成分 ４：発光層 ４ａ：発光成分 ５：電子注入輸送層 ５”：電子注入輸送層 ５ａ：電子注入輸送成分 ６：陰極 ７：電源 1: substrate 2: Anode 3: Hole injection transport layer 3a: hole injecting and transporting component 4: Light emitting layer 4a: luminous component 5: Electron injection transport layer 5 ": electron injection transport layer 5a: electron injection transport component 6: Cathode 7: Power supply
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｈ０５Ｂ 33/22 Ｈ０５Ｂ 33/22 Ｄ (72)発明者 田辺 良満 千葉県袖ケ浦市長浦580−32 三井化学株 式会社内 (72)発明者 中塚 正勝 千葉県袖ケ浦市長浦580−32 三井化学株 式会社内 Ｆターム(参考） 3K007 AB00 AB04 BB06 CA01 CA02 CA05 CB01 DA00 DB03 EB00 FA01 4H006 AA01 AB92 ─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. 7 Identification code FI theme code (reference) H05B 33/22 H05B 33/22 D (72) Inventor Yoshimitsu Tanabe 580-32 Nagaura, Sodegaura, Chiba Mitsui Chemicals Co., Ltd. In-company (72) Inventor Masakatsu Nakatsuka 580-32 Nagaura, Sodegaura-shi, Chiba Mitsui Chemicals Co., Ltd. F-term in the company (reference) 3K007 AB00 AB04 BB06 CA01 CA02 CA05 CB01 DA00 DB03 EB00 FA01 4H006 AA01 AB92
Claims (7)
合物。 【化１】 〔式中、Ａｒ1、Ａｒ2、Ａｒ3およびＡｒ4は置換または
未置換のアリール基を表し、Ｒ1、Ｒ2、Ｒ3、Ｒ4、
Ｒ5、Ｒ6、Ｒ7、Ｒ8、Ｒ9およびＲ10は、水素原子、ハ
ロゲン原子または−（Ｏ）ｎ−Ｚ基（式中Ｚは、ハロゲ
ン原子で置換されていてもよい直鎖、分岐または環状の
アルキル基、あるいは置換または未置換のアリール基を
表し、ｎは０または１を表す）を表す〕1. An amine compound represented by the general formula (1) (formula 1). [Chemical 1] [Wherein Ar 1 , Ar 2 , Ar 3 and Ar 4 represent a substituted or unsubstituted aryl group, and R 1 , R 2 , R 3 , R 4 and
R 5, R 6, R 7 , R 8, R 9 and R 10 are a hydrogen atom, a halogen atom or - (O) n-Z group (wherein Z is optionally straight optionally substituted by a halogen atom , A branched or cyclic alkyl group, or a substituted or unsubstituted aryl group, and n represents 0 or 1).
いてＡｒ1、Ａｒ2、Ａｒ3およびＡｒ4の内、少なくとも
一つがフェニル基である請求項１記載のアミン化合物。2. The amine compound according to claim 1, wherein at least one of Ar 1 , Ar 2 , Ar 3 and Ar 4 in the amine compound represented by the general formula (1) is a phenyl group.
アミン化合物を少なくとも1種含有する層を少なくとも
一層挟持してなる有機電界発光素子。3. An organic electroluminescent device comprising a pair of electrodes, and at least one layer containing at least one amine compound represented by the general formula (1) sandwiched between the pair of electrodes.
有する層が、正孔注入輸送層である請求項３記載の有機
電界発光素子。4. The organic electroluminescent device according to claim 3, wherein the layer containing the amine compound represented by the general formula (1) is a hole injecting and transporting layer.
有する層が、発光層である請求項３記載の有機電界発光
素子。5. The organic electroluminescent device according to claim 3, wherein the layer containing the amine compound represented by the general formula (1) is a light emitting layer.
請求項３または４のいずれかに記載の有機電界発光素
子。6. The organic electroluminescent device according to claim 3, further comprising a light emitting layer between the pair of electrodes.
を有する請求項３〜６のいずれかに記載の有機電界発光
素子。7. The organic electroluminescent device according to claim 3, further comprising an electron injecting and transporting layer between the pair of electrodes.
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