WO2009099060A1 - 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2009099060A1 WO2009099060A1 PCT/JP2009/051783 JP2009051783W WO2009099060A1 WO 2009099060 A1 WO2009099060 A1 WO 2009099060A1 JP 2009051783 W JP2009051783 W JP 2009051783W WO 2009099060 A1 WO2009099060 A1 WO 2009099060A1
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- Prior art keywords
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- aromatic amine
- amine derivative
- organic
- layer
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 61
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- 239000010409 thin film Substances 0.000 claims abstract description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- -1 styrylamine compound Chemical class 0.000 claims description 186
- 238000005401 electroluminescence Methods 0.000 claims description 109
- 125000004432 carbon atom Chemical group C* 0.000 claims description 76
- 238000002347 injection Methods 0.000 claims description 72
- 239000007924 injection Substances 0.000 claims description 72
- 239000000463 material Substances 0.000 claims description 71
- 230000005525 hole transport Effects 0.000 claims description 38
- 125000006413 ring segment Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
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- 238000004458 analytical method Methods 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 17
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- 125000001424 substituent group Chemical group 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
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- 239000002184 metal Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
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- 238000007740 vapor deposition Methods 0.000 description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
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- 238000001771 vacuum deposition Methods 0.000 description 10
- 239000003446 ligand Substances 0.000 description 9
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
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- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- 150000004696 coordination complex Chemical class 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 230000005684 electric field Effects 0.000 description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
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- 239000000126 substance Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 125000000732 arylene group Chemical group 0.000 description 6
- 229910052792 caesium Inorganic materials 0.000 description 6
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- 230000000694 effects Effects 0.000 description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- 238000005215 recombination Methods 0.000 description 5
- 230000006798 recombination Effects 0.000 description 5
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- 238000004544 sputter deposition Methods 0.000 description 5
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 5
- 125000005504 styryl group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XNBGHWRYLJOQAU-UHFFFAOYSA-N 1-bromo-4-(4-phenylphenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XNBGHWRYLJOQAU-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 229910001508 alkali metal halide Inorganic materials 0.000 description 4
- 150000008045 alkali metal halides Chemical class 0.000 description 4
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
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- 125000005110 aryl thio group Chemical group 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
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- 229960003540 oxyquinoline Drugs 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- NSRBXXWZFGGDPX-UHFFFAOYSA-N 2,8-dibromo-6,6,12,12-tetramethylindeno[1,2-b]fluorene Chemical compound C1=C2C3=CC=C(Br)C=C3C(C)(C)C2=CC2=C1C(C)(C)C1=CC(Br)=CC=C12 NSRBXXWZFGGDPX-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
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- 150000001412 amines Chemical group 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
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- 229910010272 inorganic material Inorganic materials 0.000 description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 229910052701 rubidium Inorganic materials 0.000 description 3
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 2
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- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 2
- ATGIXVUZFPZOHP-UHFFFAOYSA-N 4-(4-phenylphenyl)aniline Chemical group C1=CC(N)=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ATGIXVUZFPZOHP-UHFFFAOYSA-N 0.000 description 2
- SXOUNESKHJIXNK-UHFFFAOYSA-N 4-bromo-9,9-dimethylfluorene Chemical compound C1=CC=C(Br)C2=C1C(C)(C)C1=CC=CC=C12 SXOUNESKHJIXNK-UHFFFAOYSA-N 0.000 description 2
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- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 2
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
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- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzoquinoline Natural products C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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- 125000000707 boryl group Chemical group B* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
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- HHACNQLZWJFHIC-UHFFFAOYSA-N isocyano cyanate Chemical compound [C-]#[N+]OC#N HHACNQLZWJFHIC-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000005355 lead glass Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical class C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 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
- 239000012071 phase Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 150000004032 porphyrins Chemical group 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 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 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Definitions
- the present invention relates to an aromatic amine derivative and an organic electroluminescence (EL) device using the same, and in particular, by using an asymmetric aromatic amine derivative having a specific structure as a hole transporting material, luminous efficiency.
- the present invention relates to an organic EL element having a long lifetime and an aromatic amine derivative that realizes the organic EL element.
- An organic EL element is a self-luminous element utilizing the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field.
- Eastman Kodak's C.I. W. Organic materials have been constructed since Tang et al.'S report on low-voltage driven organic EL devices using stacked devices (CW Tang, SA Vanslyke, Applied Physics) Letters, 51, 913, 1987, etc.) Research on organic EL elements as materials has been actively conducted. Tang et al. Use tris (8-quinolinolato) aluminum for the light emitting layer and a triphenyldiamine derivative for the hole transporting layer.
- the element structure of the organic EL element includes a hole transport (injection) layer, a two-layer type of an electron transport light emitting layer, or a hole transport (injection) layer, a light emitting layer, and an electron transport (injection) layer.
- a hole transport (injection) layer a two-layer type of an electron transport light emitting layer, or a hole transport (injection) layer, a light emitting layer, and an electron transport (injection) layer.
- a three-layer type is well known.
- the element structure and the formation method are devised in order to increase the recombination efficiency of injected holes and electrons.
- a compound having a symmetric structure in the molecule generally has a high glass transition temperature (Tg), but has a high sublimation temperature, and when a phenomenon such as decomposition during vapor deposition or non-uniform vapor deposition occurs. This was the cause of the problem of short life.
- Tg glass transition temperature
- Patent Document 3 describes an aromatic amine derivative having an asymmetric structure, but there is no specific example, and there is no description about the characteristics of the asymmetric compound.
- Patent Document 4 describes an asymmetric aromatic amine derivative having phenanthrene as an example, but it is treated in the same way as a symmetric compound and does not describe any characteristics of the asymmetric compound. . Moreover, although the asymmetric compound requires a special synthesis method, these patents do not clearly describe the method for producing the asymmetric compound. Furthermore, Patent Document 5 describes a method for producing an aromatic amine derivative having an asymmetric structure, but does not describe the characteristics of the asymmetric compound. Patent Document 6 describes a thermally stable asymmetric compound having a high glass transition temperature, but only compounds having carbazole are exemplified. Patent Documents 7 to 9 describe aromatic amine derivatives having a fluorene structure at the center, but there is no specific description of asymmetric compounds. Moreover, there was no description about the technique which combines a carbazole and an amine compound. Although there are reports on the organic EL elements as described above, development of an organic EL element having a superior performance rather than sufficient performance has been strongly desired.
- the present invention has been made to solve the above-described problems, and an object of the present invention is to provide an organic EL device having a long lifetime and an aromatic amine derivative that realizes it while improving luminous efficiency.
- the present inventors have developed an aromatic amine derivative having a specific central skeleton and an asymmetric structure represented by the following general formula (1) for organic EL devices.
- a material particularly as a hole transport material
- the amino group substituted by the aryl group represented by General formula (2) and (3) was suitable as an amine unit which has a specific substituent. Since this amine unit can interact with the electrode, it is easy to inject charges, and an effect of lowering the driving voltage can be expected due to high mobility.
- the present invention provides an aromatic amine derivative represented by the following general formula (1).
- R 1 to R 6 each independently comprises a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted hydrocarbon having 1 to 50 carbon atoms.
- a and B are each independently represented by the following general formula (2) or (3). However, A and B are not the same.
- Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring atoms.
- the present invention provides an organic EL device in which an organic thin film layer composed of one or more layers including at least a light emitting layer is sandwiched between a cathode and an anode, wherein at least one layer of the organic thin film layer is the aromatic amine derivative.
- the organic EL element which contains these as a component of single or a mixture is provided.
- the aromatic amine derivative of the present invention is difficult to crystallize molecules, and by adding this to the organic thin film layer of the organic EL element, the yield in producing the organic EL element is improved, and the luminous efficiency is improved. An organic EL element having a long life can be obtained.
- the aromatic amine derivative of the present invention is represented by the following general formula (1).
- R 1 to R 6 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a straight chain composed of a hydrocarbon having 1 to 50 carbon atoms. Represents a branched alkyl group.
- a and B are each independently represented by the following general formula (2) or (3). However, A and B are not the same.
- a and B are each independently preferably represented by any one of the following general formulas (2), (4) and (5).
- Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring atoms.
- R 7 to R 10 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a hydrocarbon having 1 to 50 carbon atoms. Represents a linear or branched alkyl group consisting of
- substituted aryl group having 6 to 50 ring atoms include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphen
- Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of R 1 to R 6 in the general formula (1) and R 7 to R 10 in the general formulas (4) and (5) include, for example, a methyl group, Ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2, 3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloro
- substituent further substituting the aryl group and the alkyl group include, for example, an alkyl group having 1 to 8 carbon atoms (methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, Isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group); a hydroxyalkyl group having 1 to 5 carbon atoms (hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group)
- a haloalkyl group having 1 to 4 carbon atoms chloromethyl group, 1-chloroethyl
- the aromatic amine derivative of the present invention is preferably such that, in the general formula (1), at least three of Ar 1 to Ar 4 are different groups. In the general formula (1), three of Ar 1 to Ar 4 are preferably the same group. In the general formula (1), the aromatic amine derivative of the present invention is preferably such that Ar 1 and Ar 2 are the same group, and Ar 3 and Ar 4 are the same group. Further, in the general formula (1), Ar 1 and Ar 2 are biphenyl groups, and Ar 3 and Ar 4 are each independently selected from a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, and a fluorenyl group. A group is preferred.
- A is preferably the formula (2) and B is the formula (4) in the general formula (1), and Ar 1 and Ar 2 in the formula (2) are each independently And a group selected from a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group and a fluorenyl group.
- A is preferably the formula (2) and B is preferably the formula (5), and Ar 1 and Ar 2 in the formula (2) are each independently And a group selected from a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group and a fluorenyl group.
- the aromatic amine derivative of the present invention is preferably such that, in the general formula (1), A is the formula (4) and B is the formula (5).
- aromatic amine derivative represented by the general formula (1) of the present invention are shown below, but are not limited to these exemplified compounds.
- Ph represents a phenyl group
- Me represents a methyl group.
- the aromatic amine derivative of the present invention is preferably a material for an organic electroluminescence device, and particularly preferably a hole transport material for an organic electroluminescence device.
- the organic EL element of the present invention is an organic EL element in which an organic thin film layer comprising at least one light emitting layer or a plurality of layers is sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers is the aromatic Contains an amine derivative alone or as a component of a mixture.
- the organic thin film layer preferably has a hole transport layer, and the aromatic amine derivative of the present invention is preferably contained in the hole transport layer.
- the organic thin film layer has a plurality of hole transport layers, and the layer in contact with the light emitting layer contains the aromatic amine derivative of the present invention.
- the organic thin film layer has a hole injection layer, and the aromatic amine derivative of the present invention is contained in the hole injection layer.
- the organic EL device of the present invention preferably contains a styrylamine compound and / or an arylamine compound in the light emitting layer.
- a styrylamine compound include compounds represented by the following general formula (I)
- examples of the arylamine compound include compounds represented by the following general formula (II).
- Ar 8 is a group selected from phenyl, biphenylyl, terphenylyl, stilbene, and distyrylaryl
- Ar 9 and Ar 10 are each a hydrogen atom or an aromatic group having 6 to 20 carbon atoms.
- Ar 9 to Ar 10 may be substituted.
- p ′ is an integer of 1 to 4. More preferably, Ar 9 and / or Ar 10 is substituted with a styryl group.
- the aromatic group having 6 to 20 carbon atoms is preferably a phenyl group, a naphthyl group, an anthranyl group, a phenanthryl group, a terphenyl group, or the like.
- Ar 11 to Ar 13 are an optionally substituted aryl group having 5 to 40 ring carbon atoms.
- q ′ is an integer of 1 to 4.
- the aryl group having 5 to 40 ring atoms includes phenyl, naphthyl, anthranyl, phenanthryl, pyrenyl, coronyl, biphenylyl, terphenylyl, pyrrolyl, furanyl, thiophenyl, benzothiophenyl, oxadiazolyl, diphenylanthranyl, indolyl, Carbazolyl, pyridyl, benzoquinolyl, fluoranthenyl, acenaphthofluoranthenyl, stilbene and the like are preferable.
- the aryl group having 5 to 40 ring atoms may be further substituted with a substituent.
- Preferred substituents include alkyl groups having 1 to 6 carbon atoms (ethyl group, methyl group, i-propyl group). Group, n-propyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, cyclopentyl group, cyclohexyl group, etc.), alkoxy group having 1 to 6 carbon atoms (ethoxy group, methoxy group, i-propoxy group) N-propoxy group, s-butoxy group, t-butoxy group, pentoxy group, hexyloxy group, cyclopentoxy group, cyclohexyloxy group, etc.), aryl group having 5 to 40 ring atoms, ring number 5 An amino group substituted with an aryl group of ⁇ 40, an ester group having an aryl group of 5 to 40
- the organic thin film layer preferably has a plurality of hole injection and transport layers, and at least one of them is a layer containing an acceptor material.
- the acceptor material has an electron-accepting function such as Lewis acidity. -21067, JP-A-4-297076, JP-T-2004-514257, and US 2005/0255534.
- the aromatic amine derivative of the present invention is particularly preferably used for an organic EL device that emits blue light.
- the configuration (8) is usually preferably used, but is not limited thereto.
- the aromatic amine derivative of the present invention may be used in any organic thin film layer of an organic EL device, but can be used in a light emission band or a hole transport band, preferably a hole transport band, particularly preferably a hole transport.
- numerator is hard to crystallize and the yield at the time of manufacturing an organic EL element improves.
- the amount of the aromatic amine derivative of the present invention contained in the organic thin film layer is preferably 30 to 100 mol%.
- the organic EL element of this invention is produced on a translucent board
- the translucent substrate referred to here is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 to 700 nm of 50% or more.
- a glass plate, a polymer plate, etc. are mentioned.
- the glass plate include soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
- the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
- Anode of the organic EL device of the present invention has a function of injecting holes into the hole transport layer or the light emitting layer, and it is effective to have a work function of 4.5 eV or more.
- Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), indium-zinc oxide (IZO), gold, silver, platinum, copper and the like.
- the anode can be produced by forming a thin film from these electrode materials by a method such as vapor deposition or sputtering. Thus, when light emission from the light emitting layer is taken out from the anode, it is preferable that the transmittance of the anode for light emission is greater than 10%.
- the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
- the film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 to 200 nm.
- the light-emitting layer of the organic EL device has the following functions (1) to (3).
- Injection function When an electric field is applied, holes can be injected from the anode or hole injection layer, Function that can inject electrons from cathode or electron injection layer
- Transport function Function to move injected charges (electrons and holes) by the force of electric field
- Luminescent function A function that provides a field for recombination of electrons and holes and connects them to light emission.
- the transport ability represented by the mobility of holes and electrons may be large or small, it is preferable to move one of the charges.
- the light emitting layer As a method for forming the light emitting layer, for example, a known method such as a vapor deposition method, a spin coating method, or an LB method can be applied.
- the light emitting layer is particularly preferably a molecular deposited film.
- the molecular deposition film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidification from a material compound in a solution state or a liquid phase state. Can be classified from a thin film (accumulated film) formed by the LB method according to a difference in an agglomerated structure and a higher-order structure and a functional difference resulting therefrom.
- a binder such as a resin and a material compound are dissolved in a solvent to form a solution, which is then thinned by a spin coating method or the like.
- a light emitting layer can be formed.
- a known light emitting material other than the light emitting material comprising the aromatic amine derivative of the present invention may be contained in the light emitting layer as desired, as long as the object of the present invention is not impaired.
- a light emitting layer containing another known light emitting material may be laminated on the light emitting layer containing the light emitting material comprising the aromatic amine derivative of the invention.
- Examples of the light-emitting material or doping material that can be used in the light-emitting layer together with the aromatic amine derivative of the present invention include, for example, anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, and naphthaloperinone.
- Ar is a substituted or unsubstituted condensed aromatic group having 10 to 50 ring carbon atoms.
- Ar ′ is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms.
- X is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted ring group having 1 to 50 carbon atoms.
- alkyl group a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, substituted or unsubstituted, An unsubstituted arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen atom, a cyano group, a nitro group, and a hydroxy group.
- a, b and c are each an integer of 0 to 4.
- n is an integer of 1 to 3. When n is 2 or more, the numbers in [] may be the same or different. )
- R 1 to R 10 are each independently a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms.
- Ar and Ar ′ are each a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms.
- L and L ′ are a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzosilolylene group, respectively.
- m is an integer from 0 to 2
- n is an integer from 1 to 4
- s is an integer from 0 to 2
- t is an integer from 0 to 4.
- a 1 and A 2 are each independently a substituted or unsubstituted condensed aromatic ring group having 10 to 20 ring carbon atoms.
- Ar 1 and Ar 2 are each independently a hydrogen atom or a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms.
- R 1 to R 10 are each independently a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms.
- Ar 1 , Ar 2 , R 9 and R 10 may be plural, and adjacent ones may form a saturated or unsaturated cyclic structure.
- groups that are symmetrical with respect to the XY axis shown on the anthracene do not bond to the 9th and 10th positions of the central anthracene.
- R 1 to R 10 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an optionally substituted aryl group, an alkoxyl group, an aryloxy group, an alkylamino group, an alkenyl group, an arylamino group or a substituted group
- a and b each represent an integer of 1 to 5, and when they are 2 or more, R 1 s or R 2 s may be the same or different from each other R 1 or R 2 may be bonded together to form a ring, R 3 and R 4 , R 5 and R 6 , R 7 and R 8 , R 9 and R 10 L 1 is a single bond, —O—, —S—, —N (R) — (R is an alkyl group or an aryl group which may be substituted), alkylene Group or arylene group.)
- R 11 to R 20 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkoxyl group, an aryloxy group, an alkylamino group, an arylamino group, or an optionally substituted multicyclic group C, d, e, and f each represent an integer of 1 to 5, and when they are 2 or more, R 11 , R 12 , R 16, or R 17 may be the same in each case They may be different, and R 11 , R 12 , R 16, or R 17 may be bonded to form a ring, and R 13 and R 14 , R 18 and R 19 L 2 is a single bond, —O—, —S—, —N (R) — (where R is an alkyl group or an aryl group which may be substituted), alkylene Group or arylene group.)
- a 5 to A 8 are each independently a substituted or unsubstituted biphenylyl group or a substituted or unsubstituted naphthyl group.
- a 9 to A 14 are the same as defined above, and R 21 to R 23 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or 1 carbon atom.
- a fluorene compound represented by the following general formula (ix) is represented by the following general formula (ix).
- R 1 and R 2 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted amino group
- R 1 and R 2 bonded to different fluorene groups may be the same or different, and R 1 and R 2 bonded to the same fluorene group are the same.
- R 3 and R 4 may be a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic ring.
- R 3 which binds to a different fluorene group
- R 4 each other or different be the same
- the .Ar 1 and Ar 2 may be different even a total of three or more substituted or unsubstituted fused polycyclic aromatic group or a benzene ring and a heterocyclic total three or more benzene rings
- Ar 1 and Ar 2 may be the same or different
- n represents an integer of 1 to 10.
- anthracene derivatives are preferable, monoanthracene derivatives are more preferable, and asymmetric anthracene is particularly preferable.
- a phosphorescent compound can also be used as the dopant light-emitting material.
- the phosphorescent compound a compound containing a carbazole ring in the host material is preferable.
- the dopant is a compound that can emit light from triplet excitons and is not particularly limited as long as it emits light from triplet excitons, but at least one selected from the group consisting of Ir, Ru, Pd, Pt, Os, and Re.
- a metal complex containing two metals is preferable, and a porphyrin metal complex or an orthometalated metal complex is preferable.
- a host suitable for phosphorescence emission comprising a compound containing a carbazole ring is a compound having a function of causing the phosphorescence emission compound to emit light as a result of energy transfer from the excited state to the phosphorescence emission compound.
- the host compound is not particularly limited as long as it is a compound capable of transferring exciton energy to the phosphorescent compound, and can be appropriately selected according to the purpose. You may have arbitrary heterocyclic rings other than a carbazole ring.
- host compounds include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcones.
- styrylanthracene derivatives Fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, porphyrin compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinones
- Derivatives thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidene methane derivatives, distyryl pyrazine derivatives, naphthalene pens Heterocyclic tetracarboxylic anhydrides such as lene, metal complexes of phthalocyanine derivatives, 8-quinolinol derivatives, metal phthalocyanines, various metal complexes represented by metal complexes having benzoxazole and benzothiazole as ligands, polysilane compounds, poly Examples thereof include conductive polymer oligomers such as lene,
- a phosphorescent dopant is a compound that can emit light from triplet excitons. Although it is not particularly limited as long as it emits light from triplet excitons, it is preferably a metal complex containing at least one metal selected from the group consisting of Ir, Ru, Pd, Pt, Os and Re, and is preferably a porphyrin metal complex or ortho Metalated metal complexes are preferred.
- the porphyrin metal complex is preferably a porphyrin platinum complex.
- Phosphorescent compounds may be used alone or in combination of two or more. There are various ligands that form orthometalated metal complexes.
- Preferred ligands include 2-phenylpyridine derivatives, 7,8-benzoquinoline derivatives, and 2- (2-thienyl) pyridine derivatives.
- a fluorinated compound or a compound having a trifluoromethyl group introduced is preferable as a blue dopant.
- the content of the phosphorescent dopant in the light emitting layer is not particularly limited and may be appropriately selected depending on the intended purpose.
- the light emitting layer may contain a hole transport material, an electron transport material, and a polymer binder as necessary. Further, the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and most preferably 10 to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer, and it may be difficult to adjust the chromaticity. If the thickness exceeds 50 nm, the driving voltage may increase.
- the hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and has a high hole mobility and a small ionization energy of usually 5.6 eV or less.
- Such a hole injecting, as the transport layer is preferably made of a material which can transport holes to the emitting layer at a lower electric field strength,
- the hole mobility thereof is, for example, 10 4 to 10 when an electric field is applied in 6 V / cm , At least 10 ⁇ 4 cm 2 / V ⁇ sec is preferable.
- the aromatic amine derivative of the present invention when used in the hole transport zone, the aromatic amine derivative of the present invention alone may form a hole injection / transport layer, or may be mixed with other materials.
- the material for forming the hole injection and transport layer by mixing with the aromatic amine derivative of the present invention is not particularly limited as long as it has the above-mentioned preferable properties, and conventionally, charge transport of holes in an optical material is known. Any material commonly used as a material and known materials used for hole injection and transport layers of organic EL elements can be selected and used.
- a material that has a hole transporting ability and can be used in the hole transporting zone is referred to as a hole transporting material.
- the above-mentioned materials can be used.
- Porphyrin compounds (disclosed in JP-A-63-295695 etc.), aromatic tertiary amine compounds and styrylamine compounds (U.S. Pat. No. 4,127,412, JP-A-53-27033, 54-58445, 55-79450, 55-144250, 56-119132, 61-295558, 61-98353, 63-295695, etc.), and it is particularly preferable to use an aromatic tertiary amine compound.
- 4,4′-bis (N- (1-naphthyl) -N-phenylamino having two condensed aromatic rings described in US Pat.
- NPD Biphenyl
- MTDATA 3-methylphenyl -N-phenylamino triphenylamine
- inorganic compounds such as p-type Si and p-type SiC can be used as the material for the hole injection / transport layer in addition to the above-mentioned aromatic dimethylidin-based compound shown as the material for the light emitting layer.
- the hole injection and transport layer can be formed by thinning the aromatic amine derivative of the present invention by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method.
- the thickness of the hole injection / transport layer is not particularly limited, but is usually 5 nm to 5 ⁇ m.
- This hole injection and transport layer may be composed of one or more of the above-described materials as long as it contains the aromatic amine derivative of the present invention in the hole transport zone.
- a layer in which a hole injection / transport layer made of a compound different from the injection / transport layer is laminated may be used.
- an organic semiconductor layer may be provided as a layer for assisting hole injection or electron injection into the light emitting layer, and those having a conductivity of 10 ⁇ 10 S / cm or more are preferable.
- a conductive oligomer such as a thiophene-containing oligomer, an arylamine oligomer disclosed in JP-A-8-193191, a conductive dendrimer such as an arylamine dendrimer, or the like is used. Can do.
- the electron injection layer / transport layer is a layer that assists the injection of electrons into the light emitting layer and transports it to the light emitting region, and has a high electron mobility.
- the layer is made of a material that particularly adheres well to the cathode.
- an electrode in this case, a cathode
- the electron transport layer is appropriately selected with a film thickness of several nanometers to several micrometers.
- the electron mobility is at least 10 ⁇ 5 cm 2 / Vs or more when an electric field of cm is applied.
- 8-hydroxyquinoline or a metal complex of its derivative or an oxadiazole derivative is preferable.
- a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum is injected. It can be used as a material.
- examples of the oxadiazole derivative include electron transfer compounds represented by the following general formula.
- Ar 1 , Ar 2 , Ar 3 , Ar 5 , Ar 6 , Ar 9 each represents a substituted or unsubstituted aryl group, and may be the same or different from each other.
- Ar 4 , Ar 7 and Ar 8 represent a substituted or unsubstituted arylene group, which may be the same or different.
- the aryl group include a phenyl group, a biphenylyl group, an anthryl group, a perylenyl group, and a pyrenyl group.
- Examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, an anthrylene group, a peryleneylene group, and a pyrenylene group.
- Examples of the substituent include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group.
- This electron transfer compound is preferably a thin film-forming compound.
- electron transfer compound examples include the following.
- materials represented by the following general formulas (A) to (F) can also be used as materials used for the electron injection layer and the electron transport layer.
- a 1 to A 3 each independently represents a nitrogen atom or a carbon atom.
- Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 ring carbon atoms.
- Ar 2 is a hydrogen atom, substituted or unsubstituted A substituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted group An alkoxy group having 1 to 20 carbon atoms or a divalent group thereof.
- Ar 1 or Ar 2 is a substituted or unsubstituted fused ring group having 10 to 60 ring carbon atoms, a substituted or unsubstituted monoheterofused ring group having 3 to 60 ring carbon atoms, or These are divalent groups.
- L 1 , L 2 and L are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 ring carbon atoms, or A substituted or unsubstituted fluorenylene group.
- R is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 ring carbon atoms, a substituted or unsubstituted 1 to 20 carbon atoms;
- a plurality of adjacent R groups may be bonded to each other to form a carbocyclic aliphatic ring or a carbocyclic aromatic ring.
- R 1 represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 60 ring carbon atoms, a substituted or unsubstituted carbon atom having 1 to 20 carbon atoms. Or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, or —L—Ar 1 —Ar 2 .
- HAr is a nitrogen-containing heterocyclic ring having 3 to 40 carbon atoms which may have a substituent
- L is a single bond and having 6 to 60 carbon atoms which may have a substituent.
- a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms, and Ar 2 is an aryl group having 6 to 60 carbon atoms which may have a substituent or a carbon atom having 3 carbon atoms which may have a substituent.
- X and Y are each independently a saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, alkoxy group, alkenyloxy group, alkynyloxy group, hydroxy group, substituted or unsubstituted aryl group, substituted Or an unsubstituted heterocyclic ring or a structure in which X and Y are combined to form a saturated or unsaturated ring, and R 1 to R 4 are each independently hydrogen, halogen atom, substituted or unsubstituted carbon number 1 To 6 alkyl groups, alkoxy groups, aryloxy groups, perfluoroalkyl groups, perfluoroalkoxy groups, amino groups, alkylcarbonyl groups, arylcarbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, azo groups, alkylcarbonyloxy Group, arylcarbonyloxy group, alkoxycarbonyloxy group, aryloxy group Bonyloxy, sulfiny
- R 1 to R 8 and Z 2 are each independently a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aromatic group, a heterocyclic group, a substituted amino group, a substituted boryl group, an alkoxy group or an aryl group
- X, Y and Z 1 each independently represents a saturated or unsaturated hydrocarbon group, aromatic group, heterocyclic group, substituted amino group, alkoxy group or aryloxy group, and Z 1 and Z 2 substituents may be bonded to each other to form a condensed ring, and n represents an integer of 1 to 3, and when n is 2 or more, Z 1 may be different, provided that n is 1 , X, Y and R 2 are methyl groups, and R 8 is a hydrogen atom or a substituted boryl group, and n is 3 and Z 1 is not a methyl group. .
- Q 1 and Q 2 each independently represent a ligand represented by the following general formula (G), and L represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cyclohexane.
- R 1 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, substituted or unsubstituted An unsubstituted aryl group, a substituted or unsubstituted heterocyclic group.
- R 1 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, substituted or unsubstituted An unsubstituted aryl group, a substituted or unsubstituted heterocyclic group.
- Q 3 and Q 4 are the same as Q 1 and Q 2 ) Represents a quantifier.
- rings A 1 and A 2 are 6-membered aryl ring structures condensed with each other, which may have a substituent. ]
- This metal complex has strong properties as an n-type semiconductor and has a large electron injection capability. Furthermore, since the generation energy at the time of complex formation is also low, the bond between the metal of the formed metal complex and the ligand is strengthened, and the fluorescence quantum efficiency as a light emitting material is also increased.
- substituents of the rings A 1 and A 2 that form the ligand of the general formula (G) include chlorine, bromine, iodine, halogen atoms of fluorine, methyl group, ethyl group, propyl group, Substituted or unsubstituted alkyl groups such as butyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, trichloromethyl group, phenyl group, naphthyl group, 3-methyl A substituted or unsubstituted aryl group such as phenyl group, 3-methoxyphenyl group, 3-fluorophenyl group, 3-trichloromethylphenyl group, 3-trifluoromethylphenyl group, 3-nitrophenyl group, methoxy group, n- Butoxy group, t-butoxy group, trichlor
- a preferred form of the organic EL device of the present invention is a device containing a reducing dopant in an electron transporting region or an interface region between a cathode and an organic layer.
- the reducing dopant is defined as a substance capable of reducing the electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals.
- preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1 .95 eV), at least one alkali metal selected from the group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.52 eV).
- a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb, and Cs, more preferably Rb or Cs, and most preferably Cs. .
- alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the light emission luminance and extend the life of the organic EL element.
- a combination of two or more alkali metals is also preferable.
- a combination containing Cs for example, Cs and Na, Cs and K, Cs and Rb, A combination of Cs, Na and K is preferred.
- Cs the reducing ability can be efficiently exhibited, and by adding to the electron injection region, the emission luminance and the life of the organic EL element can be improved.
- an electron injection layer composed of an insulator or a semiconductor may be further provided between the cathode and the organic layer. At this time, current leakage can be effectively prevented and the electron injection property can be improved.
- an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
- preferable alkali metal chalcogenides include, for example, Li 2 O, K 2 O, Na 2 S, Na 2 Se, and Na 2 O
- preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS, and CaSe
- preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl.
- examples of preferable alkaline earth metal halides include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
- the inorganic compound which comprises an electron carrying layer is a microcrystal or an amorphous insulating thin film. If the electron transport layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include the alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides described above.
- Electrode in order to inject electrons into the electron injection, transport layer, or light emitting layer, a material having a small work function (4 eV or less), an alloy, an electrically conductive compound, and a mixture thereof are used as electrode materials. Used. Specific examples of such electrode materials include sodium, sodium / potassium alloy, magnesium, lithium, magnesium / silver alloy, aluminum / aluminum oxide, aluminum / lithium alloy, indium, and rare earth metals.
- the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
- the transmittance with respect to the light emitted from the cathode is larger than 10%.
- the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually 10 nm to 1 ⁇ m, preferably 50 to 200 nm.
- Insulating layer Since an organic EL element applies an electric field to an ultrathin film, pixel defects due to leakage or short-circuiting are likely to occur. In order to prevent this, it is preferable to insert an insulating thin film layer between the pair of electrodes.
- the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, Examples thereof include germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and a mixture or a laminate thereof may be used.
- a thin film made of an anode material is formed on a suitable light-transmitting substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 10 to 200 nm, to produce an anode.
- a hole injection layer is provided on the anode.
- the hole injection layer can be formed by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, but a uniform film can be easily obtained and pinholes are hardly generated. From the point of view, it is preferable to form by vacuum deposition.
- the deposition conditions vary depending on the compound used (the material of the hole injection layer), the crystal structure of the target hole injection layer, the recombination structure, etc.
- the source temperature is preferably selected from the range of 50 to 450 ° C., the degree of vacuum of 10 ⁇ 7 to 10 ⁇ 3 Torr, the deposition rate of 0.01 to 50 nm / second, the substrate temperature of ⁇ 50 to 300 ° C., and the film thickness of 5 nm to 5 ⁇ m. .
- the formation of the light emitting layer in which the light emitting layer is provided on the hole injection layer is also performed by thinning the organic light emitting material using a desired organic light emitting material by a method such as vacuum deposition, sputtering, spin coating, or casting.
- a vacuum deposition method from the viewpoint that a homogeneous film is easily obtained and pinholes are hardly generated.
- the light emitting layer is formed by the vacuum vapor deposition method, the vapor deposition condition varies depending on the compound used, but it can be generally selected from the same condition range as that of the hole injection layer.
- an electron injection layer is provided on the light emitting layer.
- an organic EL element can be obtained by laminating a cathode.
- the cathode is made of metal, and vapor deposition or sputtering can be used.
- vacuum deposition is preferred to protect the underlying organic layer from damage during film formation.
- the organic EL element is preferably manufactured from the anode to the cathode consistently by a single vacuum.
- each layer of the organic EL element of the present invention is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used.
- the organic thin film layer containing the compound represented by the general formula (1) used in the organic EL device of the present invention is prepared by vacuum evaporation, molecular beam evaporation (MBE), a solution dipping method dissolved in a solvent, spin It can be formed by a known method such as a coating method, a casting method, a bar coating method, a roll coating method or the like.
- the film thickness of each organic layer of the organic EL device of the present invention is not particularly limited. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur.
- the range of several nm to 1 ⁇ m is usually preferable.
- a direct current voltage is applied to the organic EL element, light emission can be observed by applying a voltage of 5 to 40 V with the anode set to + and the cathode set to a negative polarity. Further, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an alternating voltage is applied, uniform light emission is observed only when the anode has a positive polarity and the cathode has a negative polarity.
- the waveform of the alternating current to be applied may be arbitrary.
- Synthesis Example 1 (Synthesis of Intermediate 1) A 200 mL three-necked flask was charged with 20.0 g of 4-bromobiphenyl (product of Tokyo Chemical Industry Co., Ltd.), 8.64 g of sodium t-butoxy (manufactured by Wako Pure Chemical Industries), and 84 mg of palladium acetate (manufactured by Wako Pure Chemical Industries, Ltd.). . Add a stir bar, set rubber caps on both sides of the flask, set a reflux snake tube in the center neck, set a balloon filled with three-way cock and argon gas on it, and use a vacuum pump in the system three times. The argon gas in the balloon was replaced.
- the precipitated crystals were separated by filtration and vacuum dried at 60 ° C. to obtain 13.5 g of N, N-di- (4-biphenylyl) -benzylamine.
- 135 g of N, N-di- (4-biphenylyl) -benzylamine 1.35 mg of N, N-di- (4-biphenylyl) -benzylamine, 135 mg of palladium-activated carbon (manufactured by Hiroshima Wako Co., Ltd., palladium content of 10% by weight) were added, 100 mL of chloroform, ethanol 20 mL was added and dissolved.
- Synthesis Example 3 (Synthesis of Intermediate 3) A reaction was conducted in the same manner as in Synthesis Example 2 except that 4-bromo-9,9-dimethylfluorene was used instead of 4-bromo-p-terphenyl. A powder was obtained. The powder was identified as Intermediate 3 by FD-MS analysis.
- Synthesis Example 4 (Synthesis of Intermediate 4) A mixture of 17.7 g of 9-phenylcarbazole, 6.03 g of potassium iodide, 7.78 g of potassium iodate, 5.90 mL of sulfuric acid and ethanol was reacted at 75 ° C. for 2 hours. After cooling, distilled water and ethyl acetate are added to separate and extract, and the organic layer is washed with sodium bicarbonate water and distilled water, concentrated, and the resulting crude product is purified by silica gel chromatography (toluene). The obtained solid was dried under reduced pressure to obtain 21.8 g of a white solid.
- the obtained solid was purified by silica gel chromatography (toluene), and the resulting solid was washed with n-hexane and dried under reduced pressure to obtain 7.10 g of a solid.
- the powder was identified as Intermediate 4 by FD-MS analysis.
- Synthesis Example 5 (Synthesis of Intermediate 5) In the synthesis of Intermediate 2 of Synthesis Example 2, the same reaction was performed except that 4-amino-p-terphenyl was used instead of aniline and 4-bromobiphenyl was used instead of 4-bromo-p-terphenyl. As a result, 9.1 g of white powder was obtained. The powder was identified as Intermediate 5 by FD-MS analysis.
- Synthesis Example 6 (Synthesis of Intermediate 6) In the synthesis of Intermediate 2 of Synthesis Example 2, 4-amino-p-terphenyl was used instead of aniline, and 4-bromo-9,9-dimethylfluorene was used instead of 4-bromo-p-terphenyl. The reaction was conducted in the same manner except that 7.9 g of white powder was obtained. The powder was identified as Intermediate 6 by FD-MS analysis.
- the obtained solid was washed with n-hexane and dried under reduced pressure. 1.9 g of a white solid was obtained.
- the above-obtained compound and 1-naphthylphenylamine were used in the same manner as in the first reaction to obtain 1.1 g of a white solid.
- the powder was identified as Compound H1 by FD-MS analysis.
- Synthesis Example 2 (Synthesis of Compound H2) The reaction was conducted in the same manner as in Synthesis Example 1 except that Intermediate 2 was used instead of 1-naphthylphenylamine as a second reaction, and 0.7 g of a white yellow solid was obtained. The powder was identified as Compound H2 by FD-MS analysis.
- Synthesis Example 3 (Synthesis of Compound H3) The reaction was conducted in the same manner as in Synthesis Example 1 except that Intermediate 3 was used instead of 1-naphthylphenylamine as the second reaction, whereby 1.0 g of a white yellow solid was obtained. The powder was identified as Compound H3 by FD-MS analysis.
- Synthesis Example 5 (Synthesis of Compound H5) The reaction was conducted in the same manner as in Synthesis Example 4 except that 1-naphthylphenylamine was used in place of Intermediate 1 as the second reaction, whereby 1.0 g of a white solid was obtained. The powder was identified as Compound H5 by FD-MS analysis.
- Synthesis Example 6 Synthesis of Compound H6 A reaction was performed in the same manner as in Synthesis Example 4 except that Intermediate 2 was used instead of Intermediate 1 as the second reaction, whereby 0.8 g of a white solid was obtained. The powder was identified as Compound H6 by FD-MS analysis.
- Synthesis Example 7 (Synthesis of Compound H7) A reaction was conducted in the same manner as in Synthesis Example 4 except that carbazole was used instead of Intermediate 1 as the first reaction and Intermediate 3 was used as the second reaction instead of 1-naphthylphenylamine. .9 g of a white solid was obtained. The powder was identified as Compound H7 by FD-MS analysis.
- Synthesis Example 9 (Synthesis of Compound H9) The reaction was conducted in the same manner as in Synthesis Example 8 except that 1-naphthylphenylamine was used in place of Intermediate 1 as the second reaction, whereby 2.2 g of a white solid was obtained. The powder was identified as Compound H9 by FD-MS analysis.
- Synthesis Example 10 (Synthesis of Compound H10) The reaction was performed in the same manner as in Synthesis Example 8 except that Intermediate 2 was used instead of Intermediate 1 as the second reaction, to obtain 2.5 g of a white solid. The powder was identified as Compound H10 by FD-MS analysis.
- Synthesis Example 11 Synthesis of Compound H11
- the reaction was performed in the same manner as in Synthesis Example 8 except that Intermediate 3 was used instead of Intermediate 1 as the second reaction, to obtain 3.1 g of a white solid.
- the powder was identified as Compound H11 by FD-MS analysis.
- Synthesis Example 12 (Synthesis of Compound H12) The reaction was conducted in the same manner as in Synthesis Example 8 except that carbazole was used in place of Intermediate 1 as the second reaction, whereby 2.2 g of a white solid was obtained. The powder was identified as Compound H12 by FD-MS analysis.
- Synthesis Example 13 (Synthesis of Compound H13) The reaction was conducted in the same manner as in Synthesis Example 1 except that Intermediate 5 was used instead of 1-naphthylphenylamine as the second reaction, whereby 0.5 g of a white yellow solid was obtained. The powder was identified as Compound H13 by FD-MS analysis.
- Synthesis Example 14 (Synthesis of Compound H14) The reaction was performed in the same manner as in Synthesis Example 1 except that Intermediate 3 was used instead of Intermediate 1 as the second reaction, and Intermediate 6 was used instead of 1-naphthylphenylamine as the second reaction. 0.4 g of a white yellow solid was obtained. The powder was identified as Compound H14 by FD-MS analysis.
- Example 1 Manufacture of an organic EL element
- a glass substrate with an ITO transparent electrode having a thickness of 25 mm ⁇ 75 mm ⁇ 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes.
- the glass substrate with a transparent electrode line after cleaning is mounted on a substrate holder of a vacuum evaporation apparatus, and the compound H1 film having a thickness of 80 nm is first covered on the surface on which the transparent electrode line is formed so as to cover the transparent electrode.
- This H1 film functions as a hole injection layer and a hole transport layer.
- the following compound EM1 having a film thickness of 40 nm was deposited to form a film.
- an amine compound D1 having the following styryl group was deposited as a luminescent molecule so that the weight ratio of EM1 and D1 was 40: 2.
- This film functions as a light emitting layer.
- the following Alq film having a thickness of 10 nm was formed on this film. This functions as an electron injection layer.
- Li (Li source: manufactured by Saesgetter) and Alq, which are reducing dopants, and Alq were vapor-deposited to form an Alq: Li film (film thickness: 10 nm) as an electron injection layer (cathode).
- Metal Al was vapor-deposited on this Alq: Li film to form a metal cathode to form an organic EL device. Moreover, about the obtained organic EL element, luminous efficiency was measured and the luminescent color was observed. Luminous efficiency was measured using Minolta CS1000, and the luminous efficiency at 10 mA / cm 2 was calculated. Furthermore, Table 1 shows the results of measuring the half life of light emission with an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current drive.
- Example 2 production of organic EL elements
- an organic EL device was produced in the same manner except that the compounds shown in Table 1 were used as the hole transport material instead of the compound H1.
- Table 1 shows the results of measuring the luminous efficiency of the obtained organic EL device, observing the luminescent color, and further measuring the half life of light emission at an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving. .
- Comparative Examples 1-5 An organic EL device was produced in the same manner as in Example 1, except that the following Comparative Compound 1 to Comparative Compound 5 were used as the hole transport material instead of Compound H1. Further, with respect to the obtained organic EL element, the luminous efficiency was measured, the luminescent color was observed, and the half-life of light emission at an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving was measured. Shown in
- Example 15 Manufacture of organic EL elements
- An organic EL device was produced in the same manner as in Example 1 except that the following arylamine compound D2 was used instead of the amine compound D1 having a styryl group. Me is a methyl group. Further, with respect to the obtained organic EL element, the luminous efficiency was measured, the luminescent color was observed, and the half-life of light emission at an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving was measured. Shown in
- Example 16 (Production of organic EL device) An organic EL device was produced in the same manner as in Example 15 except that Compound H4 was used instead of Compound H1 as the hole transport material. Further, with respect to the obtained organic EL element, the luminous efficiency was measured, the luminescent color was observed, and the half-life of light emission at an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving was measured. Shown in Comparative Example 6 An organic EL device was produced in the same manner as in Example 15 except that the comparative compound 1 was used instead of the compound H1 as the hole transport material.
- the luminous efficiency was measured, the luminescent color was observed, and the half-life of light emission at an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving was measured. Shown in
- Example 17 (Production of organic EL device) A glass substrate with an ITO transparent electrode having a thickness of 25 mm ⁇ 75 mm ⁇ 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes.
- the glass substrate with a transparent electrode line after washing is mounted on a substrate holder of a vacuum evaporation apparatus, and the following compound H232 film having a film thickness of 60 nm is first formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed.
- This H232 film functions as a hole injection layer.
- the compound H1 layer having a thickness of 20 nm was formed on the H232 film as a hole transport material. This film functions as a hole transport layer. Further, the following compound EM1 having a film thickness of 40 nm was deposited to form a film. At the same time, an amine compound D1 having the following styryl group was deposited as a luminescent molecule so that the weight ratio of EM1 and D1 was 40: 2. This film functions as a light emitting layer. The following Alq film having a thickness of 10 nm was formed on this film. This functions as an electron injection layer.
- Li Li source: manufactured by Saesgetter
- Alq which are reducing dopants
- Alq Alq
- Metal Al was vapor-deposited on this Alq: Li film to form a metal cathode to form an organic EL device.
- luminous efficiency was measured and the luminescent color was observed.
- Luminous efficiency was measured using Minolta CS1000, and the luminous efficiency at 10 mA / cm 2 was calculated. Further, Table 2 shows the results of measuring the half life of light emission with an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving.
- Examples 18 to 30 Manufacture of organic EL elements
- An organic EL device was produced in the same manner as in Example 17 except that the compounds shown in Table 2 were used as the hole transport material instead of the compound H1.
- Table 2 shows the results of measuring the luminous efficiency of the obtained organic EL device, observing the luminescent color, and measuring the half life of light emission with an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current drive. .
- Comparative Examples 7-11 An organic EL device was produced in the same manner as in Example 17 except that Comparative Compound 1 to Comparative Compound 5 were used instead of Compound H1 as the hole transport material. Further, with respect to the obtained organic EL device, the luminous efficiency was measured, the luminescent color was observed, and the half-life of light emission at an initial luminance of 5000 cd / m 2 , room temperature and DC constant current driving was measured. Shown in
- Example 31 Manufacture of organic EL elements
- An organic EL device was produced in the same manner as in Example 17 except that the arylamine compound D2 was used instead of the amine compound D1 having a styryl group. Further, with respect to the obtained organic EL device, the luminous efficiency was measured, the luminescent color was observed, and the half-life of light emission at an initial luminance of 5000 cd / m 2 , room temperature and DC constant current driving was measured.
- Shown in Example 32 Manufacture of an organic EL device
- An organic EL device was produced in the same manner as in Example 31, except that Compound H4 was used instead of Compound H1 as the hole transport material.
- the luminous efficiency was measured, the luminescent color was observed, and the half-life of light emission at an initial luminance of 5000 cd / m 2 , room temperature and DC constant current driving was measured. Shown in
- Comparative Example 12 An organic EL device was produced in the same manner as in Example 31, except that Comparative Compound 1 was used instead of Compound H1 as the hole transport material. Further, with respect to the obtained organic EL device, the luminous efficiency was measured, the luminescent color was observed, and the half-life of light emission at an initial luminance of 5000 cd / m 2 , room temperature and DC constant current driving was measured. Shown in
- Example 33 (Production of organic EL device) An organic EL device was produced in the same manner as in Example 1 except that the following acceptor compound was formed to a thickness of 10 nm between the anode and the compound H1 film, and the thickness of the compound H1 was changed to 50 nm. Further, the obtained organic EL device was measured for luminous efficiency, observed for luminescent color, and further measured for half life of light emission with an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving. As a result, the light emission efficiency was 4.4 cd / A, the light emission color was blue, and the half life was 330 hours.
- Example 34 (Production of organic EL device) An organic EL device was produced in the same manner as in Example 33 except that Compound H4 was used instead of Compound H1. Further, the obtained organic EL device was measured for luminous efficiency, observed for luminescent color, and further measured for half life of light emission with an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving. As a result, the light emission efficiency was 5.1 cd / A, the light emission color was blue, and the half life was 390 hours.
- Comparative Example 13 An organic EL device was produced in the same manner as in Example 33 except that Comparative Compound 1 was used instead of Compound H1 as the hole transport material. Further, the obtained organic EL device was measured for luminous efficiency, observed for luminescent color, and further measured for half life of light emission with an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving. As a result, the light emission efficiency was 4.0 cd / A, the light emission color was blue, and the half life was 110 hours.
- the aromatic amine derivative of the present invention is difficult to crystallize molecules, and by containing this in the organic thin film layer of the organic EL element, the yield in manufacturing the organic EL element is improved.
- the organic EL device having improved lifetime and long lifetime can be obtained. Therefore, it is extremely useful as a material for organic EL elements with high practicality.
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Abstract
Description
しかしながら、分子内に対称な構造を有する化合物は、有機EL素子に係る薄膜を作製する際に結晶化が起こりやすく、蒸着に用いるるつぼの出口を塞いだり、結晶化に起因する薄膜の欠陥が発生し、有機EL素子の歩留り低下を招くなどの問題の原因となっていた。また、分子内に対称な構造を有する化合物は、一般的にガラス転移温度(Tg)は高いものの、昇華温度が高く、蒸着時の分解や蒸着が不均一に形成される等の現象が起こると考えられるために寿命が短いという問題の原因となっていた。
一方、非対称な芳香族アミン誘導体が開示された公知文献がある。例えば、特許文献3に、非対称な構造を有する芳香族アミン誘導体が記載されているものの具体的な実施例はなく、非対称化合物の特徴についても一切記載されていない。また、特許文献4には、フェナントレンを有する非対称な芳香族アミン誘導体が実施例として記載されているが、対称の化合物と同列に扱われているとともに、非対称化合物の特徴については一切記載されていない。また、非対称化合物は特殊な合成法が必要であるにもかかわらず、これらの特許には非対称化合物の製造方法に関する記載が明示されていない。さらに、特許文献5には、非対称な構造を有する芳香族アミン誘導体の製造法については記載されているものの、非対称化合物の特徴については記載されていない。特許文献6には、ガラス転移温度の高い熱的に安定な非対称化合物の記載があるが、カルバゾールを有する化合物しか例示がない。
また、特許文献7~9には、中心にフルオレン構造を有する芳香族アミン誘導体が記載されているが、非対称の化合物についての具体的な記載は一切なかった。また、カルバゾールとアミン化合物を組み合わせる技術については一切記載がなかった。
以上のような有機EL素子の報告はあるものの、十分な性能ではなく、より優れた性能を有する有機EL素子の開発が強く望まれていた。
また特定の置換基を有するアミンユニットとして、一般式(2)及び(3)で表されるアリール基で置換されたアミノ基が好適であることを見出した。このアミンユニットは電極と相互作用が可能なため、電荷の注入が容易であり、また、移動度が高いことにより駆動電圧が低下する効果が期待できる。また、立体障害性があるため分子間の相互作用が小さいことから、結晶化が抑制され、有機EL素子を製造する歩留を向上させることが期待できる。これら総合的な結果から得られる有機EL素子の寿命を長くする効果があり、特に青色発光素子と組み合わせることにより、顕著な高効率化と長寿命効果が得られることが判った。さらに分子量が大きい化合物において、非対称な構造を有する化合物は、蒸着温度を下げることが可能なため、蒸着時の分解を抑制し、長寿命化が可能である。
A及びBは、それぞれ独立に下記一般式(2)又は(3)で表される。ただし、AとBは同一でない。
A及びBは、それぞれ独立に下記一般式(2)又は(3)で表される。ただし、AとBは同一でない。
一般式(4)及び(5)において、R7~R10は、それぞれ独立に、水素原子、置換もしくは無置換の環形成原子数6~50のアリール基、又は炭素数1~50の炭化水素からなる直鎖もしく分岐のアルキル基を表す。
これらの中で、好ましくはフェニル基、ナフチル基、ビフェニリル基、テルフェニルイル基、フルオレニル基である。
また、前記一般式(1)において、Ar1~Ar4のうち3つが同じ基であると好ましい。
また、本発明の芳香族アミン誘導体は、前記一般式(1)において、Ar1とAr2が同じ基、かつAr3とAr4が同じ基であると好ましい。
さらに、前記一般式(1)において、Ar1及びAr2がビフェニル基であり、Ar3及びAr4が、それぞれ独立に、フェニル基、ビフェニル基、ナフチル基、ターフェニル基及びフルオレニル基から選ばれる基であると好ましい。
本発明の芳香族アミン誘導体は、前記一般式(1)においてAが(2)式であり、Bが(4)式であると好ましく、(2)式のAr1及びAr2が、それぞれ独立に、フェニル基、ビフェニル基、ナフチル基、ターフェニル基及びフルオレニル基から選ばれる基であると好ましい。
本発明の芳香族アミン誘導体は、前記一般式(1)においてAが(2)式であり、Bが(5)式であると好ましく、(2)式のAr1及びAr2が、それぞれ独立に、フェニル基、ビフェニル基、ナフチル基、ターフェニル基及びフルオレニル基から選ばれる基であると好ましい。
本発明の芳香族アミン誘導体は、前記一般式(1)においてAが(4)式であり、Bが(5)式であると好ましい。
本発明の有機EL素子は、前記有機薄膜層が正孔輸送層を有し、本発明の芳香族アミン誘導体が該正孔輸送層に含有されていると好ましい。
また、前記有機薄膜層が複数の正孔輸送層を有し、発光層に接する層に本発明の芳香族アミン誘導体が含有されていると好ましい。
さらに、前記有機薄膜層が正孔注入層を有し、本発明の芳香族アミン誘導体が該正孔注入層に含有されていると好ましい。
スチリルアミン化合物としては下記一般式(I)で表される化合物などが挙げられ、アリールアミン化合物としては下記一般式(II)で表される化合物などが挙げられる。
ここで、炭素数が6~20の芳香族基としては、フェニル基、ナフチル基、アントラニル基、フェナントリル基、テルフェニル基等が好ましい。
ここで、環形成原子数が5~40のアリール基としては、フェニル、ナフチル、アントラニル、フェナントリル、ピレニル、コロニル、ビフェニリル、テルフェニリル、ピローリル、フラニル、チオフェニル、ベンゾチオフェニル、オキサジアゾリル、ジフェニルアントラニル、インドリル、カルバゾリル、ピリジル、ベンゾキノリル、フルオランテニル、アセナフトフルオランテニル、スチルベン等が好ましい。なお、環形成原子数が5~40のアリール基は、さらに置換基により置換されていてもよく、好ましい置換基としては、炭素数1~6のアルキル基(エチル基、メチル基、i-プロピル基、n-プロピル基、s-ブチル基、t-ブチル基、ペンチル基、ヘキシル基、シクロペンチル基、シクロヘキシル基等)、炭素数1~6のアルコキシ基(エトキシ基、メトキシ基、i-プロポキシ基、n-プロポキシ基、s-ブトキシ基、t-ブトキシ基、ペントキシ基、ヘキシルオキシ基、シクロペントキシ基、シクロヘキシルオキシ基等)、環形成原子数5~40のアリール基、環形成原子数5~40のアリール基で置換されたアミノ基、環形成原子数5~40のアリール基を有するエステル基、炭素数1~6のアルキル基を有するエステル基、シアノ基、ニトロ基、ハロゲン原子(塩素、臭素、ヨウ素等)が挙げられる。
アクセプター材料とは、ルイス酸性等の電子受容性の機能を有するものであって、例えば、特開2003-031365号公報、特開2001-297883号公報、特開2000-196140号公報、特開平11-251067号公報、特開平4-297076号公報、特表2004-514257号公報及び米国2005/0255334号公報に記載された化合物が挙げられる。
本発明の芳香族アミン誘導体は、特に青色系発光する有機EL素子に用いると好ましい。
(1)有機EL素子の構成
本発明の有機EL素子の代表的な素子構成としては、
(1) 陽極/発光層/陰極
(2) 陽極/正孔注入層/発光層/陰極
(3) 陽極/発光層/電子注入層/陰極
(4) 陽極/正孔注入層/発光層/電子注入層/陰極
(5) 陽極/有機半導体層/発光層/陰極
(6) 陽極/有機半導体層/電子障壁層/発光層/陰極
(7) 陽極/有機半導体層/発光層/付着改善層/陰極
(8) 陽極/正孔注入層/正孔輸送層/発光層/電子注入層/陰極
(9) 陽極/絶縁層/発光層/絶縁層/陰極
(10)陽極/無機半導体層/絶縁層/発光層/絶縁層/陰極
(11)陽極/有機半導体層/絶縁層/発光層/絶縁層/陰極
(12)陽極/絶縁層/正孔注入層/正孔輸送層/発光層/絶縁層/陰極
(13)陽極/絶縁層/正孔注入層/正孔輸送層/発光層/電子注入層/陰極
などの構造を挙げることができる。
これらの中で通常(8) の構成が好ましく用いられるが、これらに限定されるものではない。
本発明の芳香族アミン誘導体は、有機EL素子のどの有機薄膜層に用いてもよいが、発光帯域又は正孔輸送帯域に用いることができ、好ましくは正孔輸送帯域、特に好ましくは正孔輸送層に用いることにより、分子が結晶化しにくく、有機EL素子を製造する際の歩留りが向上する。
本発明の芳香族アミン誘導体を、有機薄膜層に含有させる量としては、30~100モル%が好ましい。
本発明の有機EL素子は、透光性の基板上に作製する。ここでいう透光性基板は有機EL素子を支持する基板であり、400~700nmの可視領域の光の透過率が50%以上で平滑な基板が好ましい。
具体的には、ガラス板、ポリマー板等が挙げられる。ガラス板としては、特にソーダ石灰ガラス、バリウム・ストロンチウム含有ガラス、鉛ガラス、アルミノケイ酸ガラス、ホウケイ酸ガラス、バリウムホウケイ酸ガラス、石英等が挙げられる。またポリマー板としては、ポリカーボネート、アクリル、ポリエチレンテレフタレート、ポリエーテルサルファイド、ポリサルフォン等を挙げることができる。
本発明の有機EL素子の陽極は、正孔を正孔輸送層又は発光層に注入する機能を有するものであり、4.5eV以上の仕事関数を有することが効果的である。本発明に用いられる陽極材料の具体例としては、酸化インジウム錫合金(ITO)、酸化錫(NESA)、インジウム-亜鉛酸化物(IZO)、金、銀、白金、銅等が挙げられる。
陽極は、これらの電極物質を蒸着法やスパッタリング法等の方法で薄膜を形成させることにより作製することができる。
このように発光層からの発光を陽極から取り出す場合、陽極の発光に対する透過率が10%より大きくすることが好ましい。また、陽極のシート抵抗は、数百Ω/□以下が好ましい。陽極の膜厚は材料にもよるが、通常10nm~1μm、好ましくは10~200nmの範囲で選択される。
有機EL素子の発光層は以下(1) ~(3) の機能を併せ持つものである。
(1) 注入機能;電界印加時に陽極又は正孔注入層より正孔を注入することができ、
陰極又は電子注入層より電子を注入することができる機能
(2) 輸送機能;注入した電荷(電子と正孔)を電界の力で移動させる機能
(3) 発光機能;電子と正孔の再結合の場を提供し、これを発光につなげる機能
ただし、正孔の注入されやすさと電子の注入されやすさに違いがあってもよく、また、正孔と電子の移動度で表される輸送能に大小があってもよいが、どちらか一方の電荷を移動することが好ましい。
この発光層を形成する方法としては、例えば蒸着法、スピンコート法、LB法等の公知の方法を適用することができる。発光層は、特に分子堆積膜であることが好ましい。ここで分子堆積膜とは、気相状態の材料化合物から沈着され形成された薄膜や、溶液状態又は液相状態の材料化合物から固体化され形成された膜のことであり、通常この分子堆積膜は、LB法により形成された薄膜(分子累積膜)とは凝集構造、高次構造の相違や、それに起因する機能的な相違により区分することができる。
また、特開昭57-51781号公報に開示されているように、樹脂等の結着剤と材料化合物とを溶剤に溶かして溶液とした後、これをスピンコート法等により薄膜化することによっても、発光層を形成することができる。
本発明においては、本発明の目的が損なわれない範囲で、所望により発光層に本発明の芳香族アミン誘導体からなる発光材料以外の他の公知の発光材料を含有させてもよく、また、本発明の芳香族アミン誘導体からなる発光材料を含む発光層に、他の公知の発光材料を含む発光層を積層してもよい。
下記一般式(i)で表される非対称アントラセン。
Ar’は置換もしくは無置換の環形成炭素数6~50の芳香族基である。
Xは、置換もしくは無置換の環形成炭素数6~50の芳香族基、置換もしくは無置換の環形成原子数5~50の芳香族複素環基、置換もしくは無置換の炭素数1~50のアルキル基、置換もしくは無置換の炭素数1~50のアルコキシ基、置換もしくは無置換の炭素数6~50のアラルキル基、置換もしくは無置換の環形成原子数5~50のアリールオキシ基、置換もしくは無置換の環形成原子数5~50のアリールチオ基、置換もしくは無置換の炭素数1~50のアルコキシカルボニル基、カルボキシル基、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基である。
a、b及びcは、それぞれ0~4の整数である。
nは1~3の整数である。また、nが2以上の場合は、[ ]内は、同じでも異なっていてもよい。)
R1~R10は、それぞれ独立に、水素原子、置換もしくは無置換の環形成炭素数6~50の芳香族環基、置換もしくは無置換の環形成原子数5~50の芳香族複素環基、置換もしくは無置換の炭素数1~50のアルキル基、置換もしくは無置換のシクロアルキル基、置換もしくは無置換の炭素数1~50のアルコキシ基、置換もしくは無置換の炭素数6~50のアラルキル基、置換もしくは無置換の環形成原子数5~50のアリールオキシ基、置換もしくは無置換の環形成原子数5~50のアリールチオ基、置換もしくは無置換の炭素数1~50のアルコキシカルボニル基、置換もしくは無置換のシリル基、カルボキシル基、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基である。)
L及びL’は、それぞれ置換もしくは無置換のフェニレン基、置換もしくは無置換のナフタレニレン基、置換もしくは無置換のフルオレニレン基又は置換もしくは無置換のジベンゾシロリレン基である。
mは0~2の整数、nは1~4の整数、sは0~2の整数、tは0~4の整数である。
また、L又はArは、ピレンの1~5位のいずれかに結合し、L’又はAr’は、ピレンの6~10位のいずれかに結合する。
ただし、n+tが偶数の時、Ar,Ar’,L,L’は下記(1) 又は(2) を満たす。
(1) Ar≠Ar’及び/又はL≠L’(ここで≠は、異なる構造の基であることを示す。)
(2) Ar=Ar’かつL=L’の時
(2-1) m≠s及び/又はn≠t、又は
(2-2) m=sかつn=tの時、
(2-2-1) L及びL’、又はピレンが、それぞれAr及びAr’上の異なる結合位置に結合しているか、(2-2-2) L及びL’、又はピレンが、Ar及びAr’上の同じ結合位置で結合している場合、L及びL’又はAr及びAr’のピレンにおける置換位置が1位と6位、又は2位と7位である場合はない。]
Ar1及びAr2は、それぞれ独立に、水素原子、又は置換もしくは無置換の環形成炭素数6~50の芳香族環基である。
R1~R10は、それぞれ独立に、水素原子、置換もしくは無置換の環形成炭素数6~50の芳香族環基、置換もしくは無置換の環形成原子数5~50の芳香族複素環基、置換もしくは無置換の炭素数1~50のアルキル基、置換もしくは無置換のシクロアルキル基、置換もしくは無置換の炭素数1~50のアルコキシ基、置換もしくは無置換の炭素数6~50のアラルキル基、置換もしくは無置換の環形成原子数5~50のアリールオキシ基、置換もしくは無置換の環形成原子数5~50のアリールチオ基、置換もしくは無置換の炭素数1~50のアルコキシカルボニル基、置換もしくは無置換のシリル基、カルボキシル基、ハロゲン原子、シアノ基、ニトロ基又はヒドロキシ基である。
Ar1、Ar2、R9及びR10は、それぞれ複数であってもよく、隣接するもの同士で飽和もしくは不飽和の環状構造を形成していてもよい。
ただし、一般式(1)において、中心のアントラセンの9位及び10位に、該アントラセン上に示すX-Y軸に対して対称型となる基が結合する場合はない。)
また、ドーパントの発光材料としては、りん光発光性の化合物を用いることもできる。りん光発光性の化合物としては、ホスト材料にカルバゾール環を含む化合物が好ましい。ドーパントとしては三重項励起子から発光することのできる化合物であり、三重項励起子から発光する限り特に限定されないが、Ir、Ru、Pd、Pt、Os及びReからなる群から選択される少なくとも一つの金属を含む金属錯体であることが好ましく、ポルフィリン金属錯体又はオルトメタル化金属錯体が好ましい。
カルバゾール環を含む化合物からなるりん光発光に好適なホストは、その励起状態からりん光発光性化合物へエネルギー移動が起こる結果、りん光発光性化合物を発光させる機能を有する化合物である。ホスト化合物としては励起子エネルギーをりん光発光性化合物にエネルギー移動できる化合物ならば特に制限はなく、目的に応じて適宜選択することができる。カルバゾール環以外に任意の複素環などを有していても良い。
具体例としては、以下のような化合物が挙げられる。
オルトメタル化金属錯体を形成する配位子としては種々のものがあるが、好ましい配位子としては、2-フェニルピリジン誘導体、7,8-ベンゾキノリン誘導体、2-(2-チエニル)ピリジン誘導体、2-(1-ナフチル)ピリジン誘導体、2-フェニルキノリン誘導体等が挙げられる。これらの誘導体は必要に応じて置換基を有しても良い。特に、フッ素化物、トリフルオロメチル基を導入したものが、青色系ドーパントとしては好ましい。さらに補助配位子としてアセチルアセトナート、ピクリン酸等の上記配位子以外の配位子を有していても良い。
りん光発光性のドーパントの発光層における含有量としては、特に制限はなく、目的に応じて適宜選択することができるが、例えば、0.1~70質量%であり、1~30質量%が好ましい。りん光発光性化合物の含有量が0.1質量%未満では発光が微弱でありその含有効果が十分に発揮されず、70質量%を超える場合は、濃度消光と言われる現象が顕著になり素子性能が低下する。
また、発光層は、必要に応じて正孔輸送材、電子輸送材、ポリマーバインダーを含有しても良い。
さらに、発光層の膜厚は、好ましくは5~50nm、より好ましくは7~50nm、最も好ましくは10~50nmである。5nm未満では発光層形成が困難となり、色度の調整が困難となる恐れがあり、50nmを超えると駆動電圧が上昇する恐れがある。
正孔注入、輸送層は発光層への正孔注入を助け、発光領域まで輸送する層であって、正孔移動度が大きく、イオン化エネルギーが通常5.6eV以下と小さい。このような正孔注入、輸送層としては、より低い電界強度で正孔を発光層に輸送する材料が好ましく、さらに正孔の移動度が、例えば104~106V/cmの電界印加時に、少なくとも10-4cm2/V・秒であれば好ましい。
本発明の芳香族アミン誘導体を正孔輸送帯域に用いる場合、本発明の芳香族アミン誘導体単独で正孔注入、輸送層を形成してもよく、他の材料と混合して用いてもよい。
本発明の芳香族アミン誘導体と混合して正孔注入、輸送層を形成する材料としては、前記の好ましい性質を有するものであれば特に制限はなく、従来、光導伝材料において正孔の電荷輸送材料として慣用されているものや、有機EL素子の正孔注入、輸送層に使用される公知のものの中から任意のものを選択して用いることができる。本発明においては、正孔輸送能を有し、正孔輸送帯域に用いることが可能な材料を正孔輸送材料と呼ぶ。
また、米国特許第5,061,569号に記載されている2個の縮合芳香族環を分子内に有する、例えば、4,4’-ビス(N-(1-ナフチル)-N-フェニルアミノ)ビフェニル(以下NPDと略記する)、また特開平4-308688号公報に記載されているトリフェニルアミンユニットが3つスターバースト型に連結された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(以下MTDATAと略記する)等を挙げることができる。
さらに、発光層の材料として示した前述の芳香族ジメチリディン系化合物の他、p型Si、p型SiC等の無機化合物も正孔注入、輸送層の材料として使用することができる。
また、発光層への正孔注入又は電子注入を助ける層として有機半導体層を設けてもよく、10-10S/cm以上の導電率を有するものが好適である。このような有機半導体層の材料としては、含チオフェンオリゴマーや特開平8-193191号公報に開示してある含アリールアミンオリゴマー等の導電性オリゴマー、含アリールアミンデンドリマー等の導電性デンドリマー等を用いることができる。
次に、電子注入層・輸送層は、発光層への電子の注入を助け、発光領域まで輸送する層であって、電子移動度が大きく、また付着改善層は、この電子注入層の中で特に陰極との付着が良い材料からなる層である。
また、有機EL素子は発光した光が電極(この場合は陰極)により反射するため、直接陽極から取り出される発光と、電極による反射を経由して取り出される発光とが干渉することが知られている。この干渉効果を効率的に利用するため、電子輸送層は数nm~数μmの膜厚で適宜選ばれるが、特に膜厚が厚いとき、電圧上昇を避けるために、104~106V/cmの電界印加時に電子移動度が少なくとも10-5cm2/Vs以上であることが好ましい。
電子注入層に用いられる材料としては、8-ヒドロキシキノリンまたはその誘導体の金属錯体やオキサジアゾール誘導体が好適である。上記8-ヒドロキシキノリンまたはその誘導体の金属錯体の具体例としては、オキシン(一般に8-キノリノール又は8-ヒドロキシキノリン)のキレートを含む金属キレートオキシノイド化合物、例えばトリス(8-キノリノール)アルミニウムを電子注入材料として用いることができる。
ここでアリール基としてはフェニル基、ビフェニリル基、アントリル基、ペリレニル基、ピレニル基が挙げられる。また、アリーレン基としてはフェニレン基、ナフチレン基、ビフェニレン基、アントリレン基、ペリレニレン基、ピレニレン基などが挙げられる。また、置換基としては炭素数1~10のアルキル基、炭素数1~10のアルコキシ基またはシアノ基等が挙げられる。この電子伝達化合物は薄膜形成性のものが好ましい。
Ar1は、置換もしくは無置換の環形成炭素数6~60のアリール基、又は置換もしくは無置換の環形成炭素数3~60のヘテロアリール基であり、Ar2は、水素原子、置換もしくは無置換の環形成炭素数6~60のアリール基、置換もしくは無置換の環形成炭素数3~60のヘテロアリール基、置換もしくは無置換の炭素数1~20のアルキル基、又は置換もしくは無置換の炭素数1~20のアルコキシ基、あるいはこれらの2価の基である。ただし、Ar1及びAr2のいずれか一方は、置換もしくは無置換の環形成炭素数10~60の縮合環基、又は置換もしくは無置換の環形成炭素数3~60のモノヘテロ縮合環基、あるいはこれらの2価の基である。
L1、L2及びLは、それぞれ独立に、単結合、置換もしくは無置換の環形成炭素数6~60のアリーレン基、置換もしくは無置換の環形成炭素数3~60のヘテロアリーレン基、又は置換もしくは無置換のフルオレニレン基である。
Rは、水素原子、置換もしくは無置換の環形成炭素数6~60のアリール基、置換もしくは無置換の環形成炭素数3~60のヘテロアリール基、置換もしくは無置換の炭素数1~20のアルキル基、又は置換もしくは無置換の炭素数1~20のアルコキシ基であり、nは0~5の整数であり、nが2以上の場合、複数のRは同一でも異なっていてもよく、また、隣接する複数のR基同士で結合して、炭素環式脂肪族環又は炭素環式芳香族環を形成していてもよい。
R1は、水素原子、置換もしくは無置換の環形成炭素数6~60のアリール基、置換もしくは無置換の環形成炭素数3~60のヘテロアリール基、置換もしくは無置換の炭素数1~20のアルキル基、又は置換もしくは無置換の炭素数1~20のアルコキシ基、又は―L―Ar1―Ar2である。)で表される含窒素複素環誘導体。
(式中、HArは、置換基を有していてもよい炭素数3~40の含窒素複素環であり、Lは、単結合、置換基を有していてもよい炭素数6~60のアリーレン基、置換基を有していてもよい炭素数3~60のヘテロアリーレン基又は置換基を有していてもよいフルオレニレン基であり、Ar1は、置換基を有していてもよい炭素数6~60の2価の芳香族炭化水素基であり、Ar2は、置換基を有していてもよい炭素数6~60のアリール基又は置換基を有していてもよい炭素数3~60のヘテロアリール基である。)で表される含窒素複素環誘導体。
一般式(G)の配位子を形成する環A1及びA2の置換基の具体的な例を挙げると、塩素、臭素、ヨウ素、フッ素のハロゲン原子、メチル基、エチル基、プロピル基、ブチル基、s-ブチル基、t-ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ステアリル基、トリクロロメチル基等の置換もしくは無置換のアルキル基、フェニル基、ナフチル基、3-メチルフェニル基、3-メトキシフェニル基、3-フルオロフェニル基、3-トリクロロメチルフェニル基、3-トリフルオロメチルフェニル基、3-ニトロフェニル基等の置換もしくは無置換のアリール基、メトキシ基、n-ブトキシ基、t-ブトキシ基、トリクロロメトキシ基、トリフルオロエトキシ基、ペンタフルオロプロポキシ基、2,2,3,3-テトラフルオロプロポキシ基、1,1,1,3,3,3-ヘキサフルオロ-2-プロポキシ基、6-(パーフルオロエチル)ヘキシルオキシ基等の置換もしくは無置換のアルコキシ基、フェノキシ基、p-ニトロフェノキシ基、p-t-ブチルフェノキシ基、3-フルオロフェノキシ基、ペンタフルオロフェニル基、3-トリフルオロメチルフェノキシ基等の置換もしくは無置換のアリールオキシ基、メチルチオ基、エチルチオ基、t-ブチルチオ基、ヘキシルチオ基、オクチルチオ基、トリフルオロメチルチオ基等の置換もしくは無置換のアルキルチオ基、フェニルチオ基、p-ニトロフェニルチオ基、p-t-ブチルフェニルチオ基、3-フルオロフェニルチオ基、ペンタフルオロフェニルチオ基、3-トリフルオロメチルフェニルチオ基等の置換もしくは無置換のアリールチオ基、シアノ基、ニトロ基、アミノ基、メチルアミノ基、ジエチルアミノ基、エチルアミノ基、ジエチルアミノ基、ジプロピルアミノ基、ジブチルアミノ基、ジフェニルアミノ基等のモノまたはジ置換アミノ基、ビス(アセトキシメチル)アミノ基、ビス(アセトキシエチル)アミノ基、ビスアセトキシプロピル)アミノ基、ビス(アセトキシブチル)アミノ基等のアシルアミノ基、水酸基、シロキシ基、アシル基、メチルカルバモイル基、ジメチルカルバモイル基、エチルカルバモイル基、ジエチルカルバモイル基、プロイピルカルバモイル基、ブチルカルバモイル基、フェニルカルバモイル基等のカルバモイル基、カルボン酸基、スルフォン酸基、イミド基、シクロペンタン基、シクロヘキシル基等のシクロアルキル基、フェニル基、ナフチル基、ビフェニリル基、アントリル基、フェナントリル基、フルオレニル基、ピレニル基等のアリール基、ピリジニル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基、インドリニル基、キノリニル基、アクリジニル基、ピロリジニル基、ジオキサニル基、ピペリジニル基、モルフォリジニル基、ピペラジニル基、トリアチニル基、カルバゾリル基、フラニル基、チオフェニル基、オキサゾリル基、オキサジアゾリル基、ベンゾオキサゾリル基、チアゾリル基、チアジアゾリル基、ベンゾチアゾリル基、トリアゾリル基、イミダゾリル基、ベンゾイミダゾリル基、プラニル基等の複素環基等がある。また、以上の置換基同士が結合してさらなる6員アリール環もしくは複素環を形成しても良い。
また、より具体的に、好ましい還元性ドーパントとしては、Na(仕事関数:2.36eV)、K(仕事関数:2.28eV)、Rb(仕事関数:2.16eV)およびCs(仕事関数:1.95eV)からなる群から選択される少なくとも一つのアルカリ金属や、Ca(仕事関数:2.9eV)、Sr(仕事関数:2.0~2.5eV)、およびBa(仕事関数:2.52eV)からなる群から選択される少なくとも一つのアルカリ土類金属が挙げられる仕事関数が2.9eV以下のものが特に好ましい。これらのうち、より好ましい還元性ドーパントは、K、RbおよびCsからなる群から選択される少なくとも一つのアルカリ金属であり、さらに好ましくは、RbまたはCsであり、最も好ましのは、Csである。これらのアルカリ金属は、特に還元能力が高く、電子注入域への比較的少量の添加により、有機EL素子における発光輝度の向上や長寿命化が図られる。また、仕事関数が2.9eV以下の還元性ドーパントとして、これら2種以上のアルカリ金属の組合わせも好ましく、特に、Csを含んだ組み合わせ、例えば、CsとNa、CsとK、CsとRbあるいはCsとNaとKとの組み合わせであることが好ましい。Csを組み合わせて含むことにより、還元能力を効率的に発揮することができ、電子注入域への添加により、有機EL素子における発光輝度の向上や長寿命化が図られる。
また、電子輸送層を構成する半導体としては、Ba、Ca、Sr、Yb、Al、Ga、In、Li、Na、Cd、Mg、Si、Ta、SbおよびZnの少なくとも一つの元素を含む酸化物、窒化物または酸化窒化物等の一種単独または二種以上の組み合わせが挙げられる。また、電子輸送層を構成する無機化合物が、微結晶または非晶質の絶縁性薄膜であることが好ましい。電子輸送層がこれらの絶縁性薄膜で構成されていれば、より均質な薄膜が形成されるために、ダークスポット等の画素欠陥を減少させることができる。なお、このような無機化合物としては、上述したアルカリ金属カルコゲナイド、アルカリ土類金属カルコゲナイド、アルカリ金属のハロゲン化物およびアルカリ土類金属のハロゲン化物等が挙げられる。
陰極としては、電子注入、輸送層又は発光層に電子を注入するため、仕事関数の小さい(4eV以下)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム・カリウム合金、マグネシウム、リチウム、マグネシウム・銀合金、アルミニウム/酸化アルミニウム、アルミニウム・リチウム合金、インジウム、希土類金属などが挙げられる。
この陰極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。
ここで発光層からの発光を陰極から取り出す場合、陰極の発光に対する透過率は10%より大きくすることが好ましい。
また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm~1μm、好ましくは50~200nmである。
有機EL素子は超薄膜に電界を印可するために、リークやショートによる画素欠陥が生じやすい。これを防止するために、一対の電極間に絶縁性の薄膜層を挿入することが好ましい。
絶縁層に用いられる材料としては例えば酸化アルミニウム、弗化リチウム、酸化リチウム、弗化セ シウム、酸化セシウム、酸化マグネシウム、弗化マグネシウム、酸化カルシウム、弗化カルシウム、窒化アルミニウム、酸化チタン、酸化珪素、酸化ゲルマニウム、窒化珪素、窒化ホウ素、酸化モリブデン、酸化ルテニウム、酸化バナジウム等が挙げられ、これらの混合物や積層物を用いてもよい。
以上例示した材料及び形成方法により陽極、発光層、必要に応じて正孔注入、輸送層、及び必要に応じて電子注入、輸送層を形成し、さらに陰極を形成することにより有機EL素子を作製することができる。また陰極から陽極へ、前記と逆の順序で有機EL素子を作製することもできる。
以下、透光性基板上に陽極/正孔注入層/発光層/電子注入層/陰極が順次設けられた構成の有機EL素子の作製例を記載する。
まず、適当な透光性基板上に陽極材料からなる薄膜を1μm以下、好ましくは10~200nmの範囲の膜厚になるように蒸着やスパッタリング等の方法により形成して陽極を作製する。次に、この陽極上に正孔注入層を設ける。正孔注入層の形成は、前述したように真空蒸着法、スピンコート法、キャスト法、LB法等の方法により行うことができるが、均質な膜が得られやすく、かつピンホールが発生しにくい等の点から真空蒸着法により形成することが好ましい。真空蒸着法により正孔注入層を形成する場合、その蒸着条件は使用する化合物(正孔注入層の材料)、目的とする正孔注入層の結晶構造や再結合構造等により異なるが、一般に蒸着源温度50~450℃、真空度10-7~10-3Torr、蒸着速度0.01~50nm/秒、基板温度-50~300℃、膜厚5nm~5μmの範囲で適宜選択することが好ましい。
次に、この発光層上に電子注入層を設ける。正孔注入層、発光層と同様、均質な膜を得る必要から真空蒸着法により形成することが好ましい。蒸着条件は正孔注入層、発光層と同様の条件範囲から選択することができる。
本発明の芳香族アミン誘導体は、発光帯域や正孔輸送帯域のいずれの層に含有させるかによって異なるが、真空蒸着法を用いる場合は他の材料との共蒸着をすることができる。また、スピンコート法を用いる場合は、他の材料と混合することによって含有させることができる。
最後に陰極を積層して有機EL素子を得ることができる。
陰極は金属から構成されるもので、蒸着法、スパッタリングを用いることができる。しかし下地の有機物層を製膜時の損傷から守るためには真空蒸着法が好ましい。
この有機EL素子の作製は一回の真空引きで一貫して陽極から陰極まで作製することが好ましい。
本発明の有機EL素子の各有機層の膜厚は特に制限されないが、一般に膜厚が薄すぎるとピンホール等の欠陥が生じやすく、逆に厚すぎると高い印加電圧が必要となり効率が悪くなるため、通常は数nmから1μmの範囲が好ましい。
なお、有機EL素子に直流電圧を印加する場合、陽極を+、陰極を-の極性にして、5~40Vの電圧を印加すると発光が観測できる。また、逆の極性で電圧を印加しても電流は流れず、発光は全く生じない。さらに交流電圧を印加した場合には陽極が+、陰極が-の極性になった時のみ均一な発光が観測される。印加する交流の波形は任意でよい。
200mLの三つ口フラスコに、4-ブロモビフェニル20.0g (東京化成社品)、t-ブトキシナトリウム8.64g (和光純薬社製)、酢酸パラジウム84mg(和光純薬社製)を入れた。さらに攪拌子を入れ、フラスコの両側にラバーキャップをセットし、中央の口に還流用蛇管、その上に三方コックとアルゴンガスを封入した風船をセットし、系内を真空ポンプを用いて3回、風船内のアルゴンガスで置換した。
次に、脱水トルエン120mL(広島和光社製)、ベンジルアミン4.08mL(東京化成社製)、トリス-t-ブチルホスフィン338 μL(P(t-Bu)3、アルドリッチ社製、2.22mol/Lトルエン溶液)、をシリンジでラバーセプタムを通して加え、5分間室温で攪拌した。次に、フラスコをオイルバスにセットし、溶液を攪拌しながら徐々に120℃まで昇温した。7時間後、オイルバスからフラスコを外し反応を終了させ、アルゴン雰囲気下、12時間放置した。反応溶液を分液ロートに移し、ジクロロメタン600mLを加えて沈殿物を溶解させ、飽和食塩水120mLで洗浄後、有機層を無水炭酸カリウムで乾燥した。炭酸カリウムを濾別して得られた有機層の溶媒を留去し、得られた残渣にトルエン400mL、エタノール80mLを加え、乾燥管を付けて80℃に加熱し、残渣を完全に溶解した。その後、12時間放置し、室温まで除冷することにより再結晶化させた。析出した結晶を濾別し、60℃で真空乾燥することにより13.5g のN,N-ジ-(4-ビフェニリル)-ベンジルアミンを得た。300mLの一口フラスコに、1.35g のN,N-ジ-(4-ビフェニリル)-ベンジルアミン、パラジウム-活性炭素135mg(広島和光社製、パラジウム含有量10重量%)を入れ、クロロホルム100mL、エタノール20mLを加えて溶解した。次に、フラスコに攪拌子を入れた後、水素ガス2Lが充填された風船を装着した三方コックをフラスコに取り付け、真空ポンプを用いてフラスコ系内を水素ガスで10回置換した。減った水素ガスを新たに充填し、水素ガスの容積を再び2Lにした後、室温で激しく溶液を攪拌した。30時間攪拌後、ジクロロメタン100mLを加え、触媒を濾別した。次に、得られた溶液を分液ロートに移し、炭酸水素ナトリウム飽和水溶液50mLで洗浄後、有機層を分別し、無水炭酸カリウムで乾燥した。濾過後、溶媒を留去し、得られた残渣にトルエン50mLを加え、再結晶化させた。析出した結晶を濾別し、50℃で真空乾燥することにより0.99gのジ-4-ビフェニリルアミン(中間体1)を得た。FD-MS(フィールドディソープションマススペクトル)の分析により、中間体1と同定した。
アルゴン気流下、アニリンを5.5g、4-ブロモ-p-ターフェニルを15.7g、t-ブトキシナトリウム6.8g(広島和光社製)トリス(ジベンジリデンアセトン)ジパラジウム(0)0.46g (Pd2(dba)3、アルドリッチ社製)及び脱水トルエン300mLを入れ、80℃にて8時間反応した。
冷却後、水500mL を加え、混合物をセライト濾過し、濾液をトルエンで抽出し、無水硫酸マグネシウムで乾燥させた。これを減圧下で濃縮し、得られた粗生成物をカラム精製し、トルエンで再結晶し、それを濾取した後、乾燥したところ、10.8gの淡黄色粉末を得た。FD-MSの分析により、中間体2と同定した。
合成例2の中間体2の合成において、4-ブロモ-p-ターフェニルの代わりに4-ブロモ-9,9-ジメチルフルオレンを用いた以外は同様に反応を行ったところ、7.3gの白色粉末を得た。FD-MSの分析により、中間体3と同定した。
9-フェニルカルバゾール17.7g、ヨウ化カリウム6.03g、ヨウ素酸カリウム7.78g、硫酸5.90mL及びエタノールを入れ、75℃にて2時間反応した。
冷却後、蒸留水、酢酸エチルを加えて分液、抽出した後、重曹水、蒸留水を用いて有機層を洗浄し、濃縮し、得られた粗生成物をシリカゲルクロマトグラフィー(トルエン)で精製し、得られた固体を減圧乾燥したところ、21.8gの白色固体を得た。
アルゴン気流下、上記得られた白色固体13.1gに脱水トルエン、脱水エーテルを加え、-45℃に冷却し、n-ブチルリチウムヘキサン溶液(1.58M)を25mL滴下して、攪拌しながら1時間かけて-5℃まで昇温する。再び-45℃まで冷却し、ボロン酸トリイソプロピルエステル25mLをゆっくり滴下してから2時間反応する。
室温に戻した後、10%希塩酸溶液を加えて攪拌し、有機層を抽出する。飽和食塩水で洗浄した後、無水硫酸まマグネシウムで乾燥し、ろ別後、濃縮する。得られた固体を、シリカゲルクロマトグラフィー(トルエン)で精製し、得られた個体をn-ヘキサンで洗浄し、減圧乾燥したところ、7.10gの固体を得た。FD-MSの分析により、中間体4と同定した。
合成例2の中間体2の合成において、アニリンの代わりに4-アミノ-p-ターフェニルを用い、4-ブロモ-p-ターフェニルの代わりに4-ブロモビフェニルを用いた以外は同様に反応を行ったところ、9.1gの白色粉末を得た。FD-MSの分析により、中間体5と同定した。
合成例6(中間体6の合成)
合成例2の中間体2の合成において、アニリンの代わりに4-アミノ-p-ターフェニルを用い、4-ブロモ-p-ターフェニルの代わりに4-ブロモ-9,9-ジメチルフルオレンを用いた以外は同様に反応を行ったところ、7.9gの白色粉末を得た。FD-MSの分析により、中間体6と同定した。
第一の反応として、アルゴン気流下、中間体1を6.4g、2,8-ジブロモ-6,6,12,12-テトラメチル-6,12-ジヒドロインデノ-[1,2b]-フルオレン(WO2006-122630を参照して合成)を9.4g、Pd2(dba)3231mg、P(t-Bu)3325mg、ターシャルブトキシナトリウム2.9g、トルエンを入れて、80℃にて4時間反応した。冷却後、トルエンを加えてセライトろ過をした後ろ液を濃縮し、シリカゲルクロマトグラフィー(ヘキサン:ジクロロメタン=6:1)で精製し、得られた個体をn-ヘキサンで洗浄して減圧乾燥したところ、1.9gの白色固体を得た。
第二の反応として、上記得られた化合物と1-ナフチルフェニルアミンを第一の反応と同様に行ったところ、1.1gの白色固体を得た。FD-MSの分析により、化合物H1と同定した。
第二の反応として1-ナフチルフェニルアミンの代わりに中間体2を用いた以外は合成実施例1と同様に反応を行ったところ、0.7gの白黄色固体を得た。FD-MSの分析により、化合物H2と同定した。
第二の反応として1-ナフチルフェニルアミンの代わりに中間体3を用いた以外は合成実施例1と同様に反応を行ったところ、1.0gの白黄色固体を得た。FD-MSの分析により、化合物H3と同定した。
第一の反応として、アルゴン気流下、カルバゾールを3.2g、2,8-ジブロモ-6,6,12,12-テトラメチル-6,12-ジヒドロインデノ-[1,2b]-フルオレン(WO2006-122630を参照して合成)を9.4g、Pd2(dba)3231mg、P(t-Bu)3325mg、t-ブトキシナトリウム2.9g、トルエンを入れて、80℃にて4時間反応した。冷却後、トルエンを加えてセライトろ過をした後ろ液を濃縮し、シリカゲルクロマトグラフィー(ヘキサン:ジクロロメタン=6:1)で精製し、得られた個体をn-ヘキサンで洗浄して減圧乾燥したところ、1.2gの白色固体を得た。
第二の反応として、上記得られた化合物と中間体1を第一の反応と同様に行ったところ、0.8gの白色固体を得た。FD-MSの分析により、化合物H4と同定した。
第二の反応として中間体1の代わりに1-ナフチルフェニルアミンを用いた以外は合成実施例4と同様に反応を行ったところ、1.0gの白色固体を得た。FD-MSの分析により、化合物H5と同定した。
第二の反応として中間体1の代わりに中間体2を用いた以外は合成実施例4と同様に反応を行ったところ、0.8gの白色固体を得た。FD-MSの分析により、化合物H6と同定した。
第一の反応として中間体1の代わりにカルバゾールを用い、第二の反応として1-ナフチルフェニルアミンの代わりに中間体3を用いた以外は合成実施例4と同様に反応を行ったところ、0.9gの白色固体を得た。FD-MSの分析により、化合物H7と同定した。
第一の反応として中間体4を22.1g、2,8-ジブロモ-6,6,12,12-テトラメチル-6,12-ジヒドロインデノ-[1,2b]-フルオレン(WO2006-122630を参照して合成)を23.4g、テトラキス(トリフェニルホスフィン)パラジウム 1.38g(Pd(PPh3)4)、炭酸ナトリウム21.9g、蒸留水及びジメトキシエタンを入れ、還流下にて8時間反応した。
冷却後、反応溶液をろ過し、ろ過残渣をアセトンで、分液した水層をジクロロメタンで抽出し、集めたろ液を分液して、アセトン、ジクロロメタンを加えて分液し、ろ過残渣をアセトンで、分液した水層をジクロロメタンで抽出して、集めた有機層を蒸留水で洗浄し、濃縮し、得られた粗生成物をシリカゲルクロマトグラフィー(ヘキサン:ジクロロメタン=9:1)で精製し、得られた固体をトルエン、メタノールで再結晶して、減圧乾燥したところ、3.9gの白色固体を得た。
第二の反応として合成実施例4の第二の反応と同様に行ったところ、2.4gの白色固体を得た。FD-MSの分析により、化合物H8と同定した。
第二の反応として中間体1の代わりに1-ナフチルフェニルアミンを用いた以外は合成実施例8と同様に反応を行ったところ、2.2gの白色固体を得た。FD-MSの分析により、化合物H9と同定した。
第二の反応として中間体1の代わりに中間体2を用いた以外は合成実施例8と同様に反応を行ったところ、2.5gの白色固体を得た。FD-MSの分析により、化合物H10と同定した。
第二の反応として中間体1の代わりに中間体3を用いた以外は合成実施例8と同様に反応を行ったところ、3.1gの白色固体を得た。FD-MSの分析により、化合物H11と同定した。
第二の反応として中間体1の代わりにカルバゾールを用いた以外は合成実施例8と同様に反応を行ったところ、2.2gの白色固体を得た。FD-MSの分析により、化合物H12と同定した。
第二の反応として1-ナフチルフェニルアミンの代わりに中間体5を用いた以外は合成実施例1と同様に反応を行ったところ、0.5gの白黄色固体を得た。FD-MSの分析により、化合物H13と同定した。
第二の反応として中間体1の代わりに中間体3を用い、第二の反応として1-ナフチルフェニルアミンの代わりに中間体6を用いた以外は合成実施例1と同様に反応を行ったところ、0.4gの白黄色固体を得た。FD-MSの分析により、化合物H14と同定した。
25mm×75mm×1.1mm厚のITO透明電極付きガラス基板(ジオマティック社製)をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UVオゾン洗浄を30分間行なった。
洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に前記透明電極を覆うようにして膜厚80nmの上記化合物H1膜を正孔輸送材料として成膜した。このH1膜は、正孔注入層および正孔輸送層として機能する。さらに膜厚40nmの下記化合物EM1を蒸着し成膜した。同時に発光分子として、下記のスチリル基を有するアミン化合物D1を、EM1とD1の重量比が40:2になるように蒸着した。この膜は、発光層として機能する。
この膜上に膜厚10nmの下記Alq膜を成膜した。これは、電子注入層として機能する。この後、還元性ドーパントであるLi(Li源:サエスゲッター社製)とAlqを二元蒸着させ、電子注入層(陰極)としてAlq:Li膜(膜厚10nm)を形成した。このAlq:Li膜上に金属Alを蒸着させ金属陰極を形成し有機EL素子を形成した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察した。発光効率はミノルタ製CS1000を用いて輝度を測定し、10mA/cm2 における発光効率を算出した。さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表1に示す。
実施例1において、正孔輸送材料として化合物H1の代わりに表1記載の化合物を用いた以外は同様にして有機EL素子を作製した。
得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表1に示す。
実施例1において、正孔輸送材料として化合物H1の代わりに下記比較化合物1~比較化合物5を用いた以外は同様にして有機EL素子を作製した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表1に示す。
実施例1において、スチリル基を有するアミン化合物D1の代わりに下記アリールアミン化合物D2を用いた以外は同様にして有機EL素子を作製した。Meはメチル基である。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表1に示す。
実施例15において、正孔輸送材料として化合物H1の代わりに化合物H4を用いた以外は同様にして有機EL素子を作製した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表1に示す。
比較例6
実施例15において、正孔輸送材料として化合物H1の代わりに上記比較化合物1を用いた以外は同様にして有機EL素子を作製した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表1に示す。
25mm×75mm×1.1mm厚のITO透明電極付きガラス基板(ジオマティック社製)をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UVオゾン洗浄を30分間行なった。
洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に前記透明電極を覆うようにして膜厚60nmの下記化合物H232膜を成膜した。このH232膜は、正孔注入層として機能する。このH232膜上に膜厚20nmの上記化合物H1層を正孔輸送材料として成膜した。この膜は正孔輸送層として機能する。さらに膜厚40nmの下記化合物EM1を蒸着し成膜した。同時に発光分子として、下記のスチリル基を有するアミン化合物D1を、EM1とD1の重量比が40:2になるように蒸着した。この膜は、発光層として機能する。
この膜上に膜厚10nmの下記Alq膜を成膜した。これは、電子注入層として機能する。この後、還元性ドーパントであるLi(Li源:サエスゲッター社製)とAlqを二元蒸着させ、電子注入層(陰極)としてAlq:Li膜(膜厚10nm)を形成した。このAlq:Li膜上に金属Alを蒸着させ金属陰極を形成し有機EL素子を形成した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察した。発光効率はミノルタ製CS1000を用いて輝度を測定し、10mA/cm2 における発光効率を算出した。さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表2に示す。
実施例17において、正孔輸送材料として化合物H1の代わりに表2に記載の化合物を用いた以外は同様にして有機EL素子を作製した。
得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表2に示す。
実施例17において、正孔輸送材料として化合物H1の代わりに比較化合物1~比較化合物5を用いた以外は同様にして有機EL素子を作製した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表2に示す。
実施例17において、スチリル基を有するアミン化合物D1の代わりに上記アリールアミン化合物D2を用いた以外は同様にして有機EL素子を作製した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表2に示す。
実施例32(有機EL素子の製造)
実施例31において、正孔輸送材料として化合物H1の代わりに化合物H4を用いた以外は同様にして有機EL素子を作製した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表2に示す。
実施例31において、正孔輸送材料として化合物H1の代わりに上記比較化合物1を用いた以外は同様にして有機EL素子を作製した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した結果を表2に示す。
実施例1において、陽極と化合物H1膜の間に下記アクセプター化合物を10nm成膜し、化合物H1の厚膜を50nmに変えた以外は同様にして有機EL素子を作製した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した。その結果、発光効率は4.4cd/A、発光色は青色であり、半減寿命は330時間であった。
実施例33において、化合物H1の代わりに化合物H4を用いた以外は同様にして有機EL素子を作製した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した。その結果、発光効率は5.1cd/A、発光色は青色であり、半減寿命は390時間であった。
実施例33において、正孔輸送材料として化合物H1の代わりに上記比較化合物1を用いた以外は同様にして有機EL素子を作製した。
また、得られた有機EL素子について、発光効率を測定し、発光色を観察し、さらに、初期輝度5000cd/m2、室温、DC定電流駆動での発光の半減寿命を測定した。その結果、発光効率は4.0cd/A、発光色は青色であり、半減寿命は110時間であった。
Claims (20)
- 前記一般式(1)において、Ar1~Ar4のうち少なくとも3つ以上は異なる基である請求項1記載の芳香族アミン誘導体
- 前記一般式(1)において、Ar1~Ar4のうち3つが同じ基である請求項1記載の芳香族アミン誘導体。
- 前記一般式(1)において、Ar1とAr2が同じ基、かつAr3とAr4が同じ基である請求項1記載の芳香族アミン誘導体。
- 前記一般式(1)において、Ar1及びAr2がビフェニル基であり、Ar3及びAr4が、それぞれ独立に、フェニル基、ビフェニル基、ナフチル基、ターフェニル基及びフルオレニル基から選ばれる基である請求項1記載の芳香族アミン誘導体。
- 前記一般式(1)において、Aが(2)式であり、Bが(4)式である請求項6記載の芳香族アミン誘導体。
- 前記一般式(2)式のAr1及びAr2が、それぞれ独立に、フェニル基、ビフェニル基、ナフチル基、ターフェニル基及びフルオレニル基から選ばれる基である請求項7記載の芳香族アミン誘導体。
- 前記一般式(1)において、Aが(2)式であり、Bが(5)式である請求項6記載の芳香族アミン誘導体。
- 前記一般式(2)のAr1及びAr2が、それぞれ独立に、フェニル基、ビフェニル基、ナフチル基、ターフェニル基及びフルオレニル基から選ばれる基である請求項9記載の芳香族アミン誘導体。
- 前記一般式(1)において、Aが(4)式であり、Bが(5)式である請求項6記載の芳香族アミン誘導体。
- 有機エレクトロルミネッセンス素子用材料である請求項1に記載の芳香族アミン誘導体。
- 有機エレクトロルミネッセンス素子用正孔輸送材料である請求項1に記載の芳香族アミン誘導体。
- 陰極と陽極間に少なくとも発光層を含む一層又は複数層からなる有機薄膜層が挟持されている有機エレクトロルミネッセンス素子において、該有機薄膜層の少なくとも1層が、請求項1に記載の芳香族アミン誘導体を単独もしくは混合物の成分として含有する有機エレクトロルミネッセンス素子。
- 前記有機薄膜層が正孔輸送層を有し、前記芳香族アミン誘導体が該正孔輸送層に含有されている請求項14記載の有機エレクトロルミネッセンス素子。
- 前記有機薄膜層が複数の正孔輸送層を有し、発光層に接する層に前記芳香族アミン誘導体が含有されている請求項14記載の有機エレクトロルミネッセンス素子。
- 前記有機薄膜層が正孔注入層を有し、前記芳香族アミン誘導体が該正孔注入層に含有されている請求項14記載の有機エレクトロルミネッセンス素子。
- 発光層にスチリルアミン化合物及び/又はアリールアミン化合物を含有する請求項14記載の有機エレクトロルミネッセンス素子。
- 前記有機薄膜層が複数の正孔注入、輸送層を有し、そのうち少なくとも1層が、アクセプター材料を含有する層である請求項14に記載の有機エレクトロルミネッセンス素子。
- 青色系発光する請求項14記載の有機エレクトロルミネッセンス素子。
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WO2011021520A1 (ja) * | 2009-08-19 | 2011-02-24 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2011523943A (ja) * | 2008-05-19 | 2011-08-25 | メルク パテント ゲーエムベーハー | 電子デバイスのための化合物 |
WO2012067425A1 (en) * | 2010-11-16 | 2012-05-24 | Rohm And Haas Electronic Materials Korea Ltd. | Novel compound for organic electronic material and organic electroluminescent device using the same |
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CN101932550A (zh) | 2010-12-29 |
KR20100116180A (ko) | 2010-10-29 |
JP5400623B2 (ja) | 2014-01-29 |
JPWO2009099060A1 (ja) | 2011-05-26 |
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