JP2009542735A - 有機エレクトロルミネセンス素子のための新規な材料 - Google Patents
有機エレクトロルミネセンス素子のための新規な材料 Download PDFInfo
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- JP2009542735A JP2009542735A JP2009518737A JP2009518737A JP2009542735A JP 2009542735 A JP2009542735 A JP 2009542735A JP 2009518737 A JP2009518737 A JP 2009518737A JP 2009518737 A JP2009518737 A JP 2009518737A JP 2009542735 A JP2009542735 A JP 2009542735A
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- 239000000463 material Substances 0.000 title claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- 239000002019 doping agent Substances 0.000 claims abstract description 18
- 230000005525 hole transport Effects 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 239000010410 layer Substances 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 23
- -1 NR 2 Inorganic materials 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 12
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- 238000006243 chemical reaction Methods 0.000 claims description 7
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- 125000001931 aliphatic group Chemical group 0.000 claims description 5
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- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
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- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 230000008707 rearrangement Effects 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005401 electroluminescence Methods 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
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- 125000004104 aryloxy group Chemical group 0.000 claims description 2
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- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
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- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 238000001465 metallisation Methods 0.000 claims 1
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000000859 sublimation Methods 0.000 description 23
- 230000008022 sublimation Effects 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 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
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 125000005504 styryl group Chemical group 0.000 description 5
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 4
- XRIIIMYMXYEIIJ-UHFFFAOYSA-N 2-[1-(9,9-dimethylfluoren-2-yl)naphthalen-2-yl]propan-2-ol Chemical compound C1=CC=C2C(C)(C)C3=CC(C4=C5C=CC=CC5=CC=C4C(C)(O)C)=CC=C3C2=C1 XRIIIMYMXYEIIJ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical class C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- DXNHBKDQBSVFMP-UHFFFAOYSA-N ethyl 1-(9,9-dimethylfluoren-2-yl)naphthalene-2-carboxylate Chemical compound C1=CC=C2C(C)(C)C3=CC(C4=C5C=CC=CC5=CC=C4C(=O)OCC)=CC=C3C2=C1 DXNHBKDQBSVFMP-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 238000004007 reversed phase HPLC Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 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 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- KLOJVXJFELYSBZ-UHFFFAOYSA-N 2-[1-(4-phenylphenyl)naphthalen-2-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=C2C=CC=CC2=C1C(C=C1)=CC=C1C1=CC=CC=C1 KLOJVXJFELYSBZ-UHFFFAOYSA-N 0.000 description 3
- PMVWTSNKNLGHEY-UHFFFAOYSA-N 9h-fluoren-3-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3CC2=C1 PMVWTSNKNLGHEY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
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- 238000010561 standard procedure Methods 0.000 description 3
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- 150000003462 sulfoxides Chemical class 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- DMDPAJOXRYGXCB-UHFFFAOYSA-N (9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DMDPAJOXRYGXCB-UHFFFAOYSA-N 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- PJZQWOXODZGQME-UHFFFAOYSA-N 2-(1-dibenzofuran-2-ylnaphthalen-2-yl)propan-2-ol Chemical compound C1=CC=C2C3=CC(C4=C5C=CC=CC5=CC=C4C(C)(O)C)=CC=C3OC2=C1 PJZQWOXODZGQME-UHFFFAOYSA-N 0.000 description 2
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical class NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 2
- MAQGRAKXKKUJFJ-UHFFFAOYSA-N 6,6,12,12-tetramethyl-N,N-diphenylindeno[2,1-h]fluoren-1-amine Chemical compound C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=2C=3C=C4C(=CC=3C(C1=2)(C)C)C1=CC=CC=C1C4(C)C MAQGRAKXKKUJFJ-UHFFFAOYSA-N 0.000 description 2
- GGQAGSRRWAVIBL-UHFFFAOYSA-N 7,7-dimethyl-9-phenylbenzo[c]fluorene Chemical compound C1=C2C(C)(C)C3=CC=C4C=CC=CC4=C3C2=CC=C1C1=CC=CC=C1 GGQAGSRRWAVIBL-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- FKIFDWYMWOJKTQ-UHFFFAOYSA-N 9-bromo-10-naphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 FKIFDWYMWOJKTQ-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
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- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-UHFFFAOYSA-N 0.000 description 1
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- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 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
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 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
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- KPZYAGQLBFUTMA-UHFFFAOYSA-K tripotassium;phosphate;trihydrate Chemical compound O.O.O.[K+].[K+].[K+].[O-]P([O-])([O-])=O KPZYAGQLBFUTMA-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
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- 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
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- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
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Abstract
【選択図】なし
Description
1.通常使用される化合物は、十分に低いLUMO(最低空分子軌道)を有していない。より低いLUMOを有する化合物は、より容易な電子注入のために、それゆえ、動作電圧の低下のために必要とされる。
Yは、出現毎に同一であるか異なり、CR1若しくはNであり;
Zは、ブリッジXが基Zに結合するならばCと等しく、ブリッジXが基Zに結合しないならばYと等しく;
Xは、出現毎に同一であるか異なり、B(R1)、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)及びP(=O)R1より選択される二価のブリッジであり;
R1は、出現毎に同一であるか異なり、H、F、Cl、Br、I、CHO、N(Ar)2、C(=O)Ar、P(=O)Ar2、S(=O)Ar、S(=O)2Ar、CR2=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、OSO2R2、又は1〜40個のC原子を有する直鎖アルキル、アルコキシ若しくはチオアルコキシ基、又は3〜40個のC原子を有する分岐或いは環状アルキル、アルコキシ若しくはチオアルコキシ基(夫々は、1以上の基R2により置換されていてもよく、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S若しくはCONR2で置き代えられていてもよく、また、1以上のH原子は、F、Cl、Br、I、CN若しくはNO2で置き代えられていてもよい)、又は各場合に1以上の基R2により置換されていてもよい5〜40個の芳香族環原子を有する芳香族若しくは複素環式芳香族環構造、又は1以上の基R2基により置換されていてもよい5〜40個の芳香族環原子を有するアリールオキシ若しくはヘテロアリールオキシ基、又は、これらの構造の組み合わせであり;ここで、2以上の隣接する置換基R1は、互いにモノ或いはポリ環状環構造を形成するものであってもよく;
Arは、出現毎に同一であるか異なり、1以上の非芳香族基R1により置換されていてもよい5〜30個の芳香族環原子を有する芳香族若しくは複素環式芳香族環構造であり、ここで、同一の窒素若しくは燐原子上に結合する2個の基Arは、単結合若しくはB(R2)、C(R2)2、Si(R2)2、C(=O)、C=NR2、C=C(R2)2、O、S、S=O、SO2、N(R2)、P(R2)及びP(=O)(R2)から選ばれるブリッジにより互いに連結してもよく、
R2は、出現毎に同一であるか異なり、H又は1〜20個のC原子を有する脂肪族、芳香族及び/又は複素環式芳香族炭化水素基であって、加えて、H原子はFで置き換えられてもよく;ここで、2以上の隣接する置換基R2は、互いにモノ或いはポリ環状、脂肪族若しくは芳香族環構造を形成するものであってもよく;
a、b、c、dは、出現毎に同一であるか異なり、0若しくは1であるが、但し、a+b=1若しくは2及びc+d=1若しくは2であり、ここで、a=0若しくはb=0若しくはc=0若しくはd=0は、各場合に、対応するブリッジXが存在しないことを意味し、そのときXは、単結合を表さない。)
式(1)〜式(6)の化合物は、好ましくは、70℃より大きい、特に、好ましくは、100℃より大きい、非常に特に、好ましくは、130℃より大きいガラス転移温度TGを有する。
Eは、単結合、O、S、N(R2)若しくはC(R2)2を表わし;
Ar1は、出現毎に同一であるか異なり、5〜20個の芳香族環原子を有するアリール若しくはヘテロアリール基、又は15〜30個の芳香族環原子を有するトリアリールアミン基(夫々は、1以上の基R2若しくはBrにより置換されていてもよい。)、好ましくは、6〜14個の芳香族環原子を有するアリール若しくはヘテロアリール基、又は18〜30個の芳香族環原子を有する、好ましくは、18〜22個の芳香族環原子を有するトリアリールアミン基(夫々は、1以上の基R2若しくはBrにより置換されていてもよい。)であり;
pは、出現毎に同一であるか異なり、0若しくは1である。
例1:1,2-ベンゾ-3,8-ビス(N,N-ジフェニルアミノ)-6,6,12,12-テトラメチル-6,12-ジヒドロインデノ[1,2-b]フルオレン
a)エチル1-(9,9-ジメチル-9H-フルオレン-2-イル)ナフタレン-2-カルボキシレート
a)1,2-ベンゾ-3-ブロモ-6,6,12,12-テトラメチル-6,12-ジヒドロインデノ[1,2-b]フルオレン
a)3,4-ベンゾ-6,6,12,12-テトラメチル-6,12-ジヒドロインデノ[1,2-b]フルオレン
a)2,3-ベンゾ-6,6,12,12-テトラメチル-6,12-ジヒドロインデノ[1,2-b]フルオレン
a)エチル1-(ジベンゾフラン-2-イル)ナフタレン-2-カルボキシレート
a)エチル1-ビフェニル-4-イルナフタレン-2-カルボキシレート
OLEDが、WO 04/058911に記載される一般的プロセスにより製造されるが、これは、特別な状況(例えば、最適な効率と色を達成するための層の厚さの変化)に対する個々の場合において適合される。
Claims (16)
- 式(1)、(2)、(3)、(4)、(5)及び(6)の化合物。
Yは、出現毎に同一であるか異なり、CR1若しくはNであり;
Zは、ブリッジXが基Zに結合するならばCと等しく、ブリッジXが基Zに結合しないならばYと等しく;
Xは、出現毎に同一であるか異なり、B(R1)、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)及びP(=O)R1より選択される二価のブリッジであり;
R1は、出現毎に同一であるか異なり、H、F、Cl、Br、I、CHO、N(Ar)2、C(=O)Ar、P(=O)Ar2、S(=O)Ar、S(=O)2Ar、CR2=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、OSO2R2、又は1〜40個のC原子を有する直鎖アルキル、アルコキシ若しくはチオアルコキシ基、又は3〜40個のC原子を有する分岐或いは環状アルキル、アルコキシ若しくはチオアルコキシ基(夫々は、1以上の基R2により置換されていてもよく、1以上の隣接しないCH2基は、R2C=CR2、-C≡C-、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S若しくはCONR2で置き代えられていてもよく、また、1以上のH原子は、F、Cl、Br、I、CN若しくはNO2で置き代えられていてもよい)、又は各場合に1以上の基R2により置換されていてもよい5〜40個の芳香族環原子を有する芳香族若しくは複素環式芳香族環構造、又は1以上の基R2基により置換されていてもよい5〜40個の芳香族環原子を有するアリールオキシ若しくはヘテロアリールオキシ基、又は、これらの構造の組み合わせであり;ここで、2個以上の隣接する置換基R1は、互いにモノ或いはポリ環状環構造を形成するものであってもよく;
Arは、出現毎に同一であるか異なり、1以上の非芳香族基R1により置換されていてもよい5〜30個の芳香族環原子を有する芳香族若しくは複素環式芳香族環構造であり;ここで、同一の窒素若しくは燐原子上に結合する2個の基Arは、単結合若しくはB(R2)、C(R2)2、Si(R2)2、C(=O)、C=NR2、C=C(R2)2、O、S、S=O、SO2、N(R2)、P(R2)及びP(=O)(R2)から選ばれるブリッジにより互いに連結してもよく、
R2は、出現毎に同一であるか異なり、H又は1〜20個のC原子を有する脂肪族、芳香族及び/又は複素環式芳香族炭化水素基であって、加えて、H原子はFで置き代えられてもよく;ここで、2個以上の隣接する置換基R2は、互いにモノ或いはポリ環状、脂肪族若しくは芳香族環構造を形成するものであってもよく;
a、b、c、dは、出現毎に同一であるか異なり、0若しくは1であるが、但し、a+b=1若しくは2及びc+d=1若しくは2であり、ここで、a=0若しくはb=0若しくはc=0若しくはd=0は、各場合に、対応するブリッジXが存在しないことを意味する。) - 添字a、b、c及びdに対して、a+b=1でc+d=1であることを特徴とする、請求項1記載の化合物。
- 記号Yが、合計0、1、2、3若しくは4回、窒素を表わし、その他の記号Yは、CR1を表わすことを特徴とする、請求項1〜3何れか1項記載の化合物。
- 記号R1は、式(1)〜(6)の芳香族親構造に結合し、出現毎に同一であるか異なり、H、F、Br、C(=O)Ar、P(=O)Ar2、CR2=CR2Ar、又は1〜5個のC原子を有する直鎖アルキル基、又は3〜5個のC原子を有する分岐アルキル基(1以上の隣接しないCH2基は、-R2C=CR2-、-C≡C-若しくはOで置き代えられていてもよく、また、1以上のH原子は、Fで置き代えられていてもよい)、又は1以上の基R2により置換されていてもよい18〜30個のC原子を有するトリアリールアミン基、又は6〜16個のC原子を有するアリール基、又は2〜16個C原子を有するヘテロアリール基、又はスピロビフルオレン基(夫々、1以上の基R2により置換されていてもよい。)、又は、2若しくは3個のこれらの構造の組み合わせを表わすことを特徴とし、及び/又は、少なくとも一つの記号R1は、式(29)若しくは(30)の基N(Ar)2を表わすことを特徴とする、請求項1〜5何れか1項記載の化合物。
Eは、単結合、O、S、N(R2)若しくはC(R2)2を表わし;
Ar1は、出現毎に同一であるか異なり、5〜20個の芳香族環原子を有するアリール若しくはヘテロアリール基、又は15〜30個の芳香族環原子を有するトリアリールアミン基(夫々は、1以上の基R2により置換されていてもよい。)、好ましくは、6〜14個の芳香族環原子を有するアリール若しくはヘテロアリール基、又は18〜30個の芳香族環原子を有するトリアリールアミン基(夫々は、1以上の基R2により置換されていてもよい。)であり;
pは、出現毎に同一であるか異なり、0若しくは1である。) - 記号Xは、出現毎に同一であるか異なり、C(R1)2、C=O、C=NR1、O、S、S=O、SO2、N(R1)、P(R1)若しくはP(=O)R1から選択される二価のブリッジであることを特徴とする、請求項1〜6何れか1項記載の化合物。
- ブリッジXに結合する基R1は、同一であるか異なり、H、又は1〜5個のC原子を有する直鎖アルキル基、又は3〜5個のC原子を有する分岐アルキル基(1以上の隣接しないCH2基は、-R2C=CR2-、-C≡C-若しくはOで置き代えられていてもよく、また、1以上のH原子は、Fで置き代えられていてもよい)、又は6〜16個のC原子を有するアリール基、又は2〜16個C原子を有するヘテロアリール基(夫々は、1以上の基R2により置換されていてもよい。)、又は、2若しくは3個のこれらの構造の組み合わせであり;ここで、同じブリッジ原子に結合する2個の基R1は、互いに環構造を形成してもよいことを特徴とするか、基R1は、式(1)〜(4)の化合物が溶液から加工されるならば、10個までのC原子を有するアルキル基を表わすことを特徴とする、請求項1〜7何れか1項記載の化合物。
- 1以上の基R1が、二量体、三量体、四量体若しくは五量体単位への結合か、ポリマー、オリゴマー若しくはデンドリマーへの結合を表わすことを特徴とする、請求項1〜8何れか1項記載の1以上の化合物を含む二量体、三量体、四量体、五量体、オリゴマー、ポリマー、若しくはデンドリマー。
- 反応性基を保持するフルオレンを、夫々反応性基を保持するカルボニル官能化ナフタレン、フェナントレン若しくはアントラセンへのカップリングと、引き続くアルキル-或いはアリール-金属試薬の内部転位と酸触媒閉環反応によって、請求項1〜8何れか1項記載の化合物を調製する方法。
- 対応する非官能化化合物のアルキル化或いはアシル化若しくは非官能化化合物のハロゲン化により、引き続く反応性芳香族化合物或いはモノ或いは2置換アミンへのカップリングにより、又は非官能化化合物のハロゲン化と引き続く金属化と求電子試薬との反応により、請求項1〜8何れか1項記載の官能化化合物を調製する方法。
- 請求項1〜9何れか1項記載の化合物の電子素子での使用。
- 陽極、陰極及び請求項1〜9何れか1項記載の少なくとも1つの化合物を含む少なくとも1つの有機層を含む素子。
- 有機エレクトロルミネセンス素子(OLED、PLED)、有機電界効果トランジスタ(O-FET)、有機薄膜トランジスタ(O-TFT)、有機発光トランジスタ(O-LET)、有機集積回路(O-IC)、有機太陽電池(O-SC)、有機電場消光素子(O-FQD)、発光電子化学電池(LEC)、有機レーザーダイオード(O-laser)及び有機光受容器から選択される請求項13記載の素子。
- 陽極、陰極、1以上の発光層及び場合によっては、各場合に、1以上の正孔注入層、正孔輸送層、電子輸送層、電子注入層及び/又は電荷生成層から選択される更なる層を含むことを特徴とする、請求項14記載の有機エレクトロルミネセンス素子。
- 1以上の置換基R1が、単純或いは縮合アリール若しくヘテロアリール基から選択され、請求項1〜8何れか1項記載の化合物が、蛍光ドーパントのためのマトリックス体料として使用されることを特徴とする、及び/又は、1以上の置換基R1及び/又はブリッジXが、少なくとも一つの基、C=O、P(=O)及び/又はSO2を含み、請求項1〜8何れか1項記載の化合物が、燐光ドーパントのためのマトリックス材料として使用されること特徴とする、及び/又は、1以上の置換基R1が、少なくとも一つのビニルアリール単位、少なくとも一つのビニルアリールアミン単位及び/又は少なくとも一つのアリールアミノ単位を含み、請求項1〜8何れか1項記載の化合物が、発光体料として使用されることを特徴とする、及び/又は、1以上の置換基R1が、N(Ar)2を表わし、請求項1乃至8何れか1項記載の化合物が、随意に電子受容体化合物でドープされてもよく、正孔輸送材料若しくは正孔注入材料として、好ましくは、正孔輸送若しくは正孔注入層に使用されることを特徴とする、及び/又は、1以上の置換基R1が、少なくとも一つの単位C=O、P(=O)及び/又はSO2を含み、請求項1〜8何れか1項記載の化合物が、随意に、電子供与性化合物でドープされてもよく、電子輸送材料として使用されることを特徴とする、請求項14又は15記載の有機エレクトロルミネセンス素子。
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CN101490207A (zh) | 2009-07-22 |
US20090261717A1 (en) | 2009-10-22 |
JP2015007050A (ja) | 2015-01-15 |
US8241763B2 (en) | 2012-08-14 |
EP2038370B1 (de) | 2012-04-25 |
KR20080109000A (ko) | 2008-12-16 |
TW200808683A (en) | 2008-02-16 |
CN101490207B (zh) | 2013-05-22 |
DE102006031990A1 (de) | 2008-01-17 |
EP2038370A1 (de) | 2009-03-25 |
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ATE555181T1 (de) | 2012-05-15 |
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