JP2010083876A - 有機半導体材料、及びこれを用いた発光素子、発光装置、照明装置、及び電子機器 - Google Patents
有機半導体材料、及びこれを用いた発光素子、発光装置、照明装置、及び電子機器 Download PDFInfo
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- JP2010083876A JP2010083876A JP2009203827A JP2009203827A JP2010083876A JP 2010083876 A JP2010083876 A JP 2010083876A JP 2009203827 A JP2009203827 A JP 2009203827A JP 2009203827 A JP2009203827 A JP 2009203827A JP 2010083876 A JP2010083876 A JP 2010083876A
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- 239000000463 material Substances 0.000 title claims abstract description 184
- 239000004065 semiconductor Substances 0.000 title claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 114
- 125000004432 carbon atom Chemical group C* 0.000 claims description 88
- 125000003118 aryl group Chemical group 0.000 claims description 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
- 229910052799 carbon Inorganic materials 0.000 claims description 69
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 56
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 150000004866 oxadiazoles Chemical class 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 20
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 125000004986 diarylamino group Chemical group 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000005286 illumination Methods 0.000 claims 1
- 230000005525 hole transport Effects 0.000 abstract description 37
- 230000021615 conjugation Effects 0.000 abstract description 8
- 230000007423 decrease Effects 0.000 abstract description 5
- 230000003247 decreasing effect Effects 0.000 abstract 1
- -1 1,5-naphthyridinyl group Chemical group 0.000 description 233
- 239000010410 layer Substances 0.000 description 208
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 195
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- 239000000126 substance Substances 0.000 description 110
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- 239000012046 mixed solvent Substances 0.000 description 87
- 239000000203 mixture Substances 0.000 description 86
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- 238000006722 reduction reaction Methods 0.000 description 68
- 238000007254 oxidation reaction Methods 0.000 description 62
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 58
- 238000002484 cyclic voltammetry Methods 0.000 description 54
- 239000000243 solution Substances 0.000 description 54
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000000758 substrate Substances 0.000 description 44
- 238000005259 measurement Methods 0.000 description 42
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- 239000000706 filtrate Substances 0.000 description 38
- 230000003647 oxidation Effects 0.000 description 38
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 34
- 239000002904 solvent Substances 0.000 description 33
- 230000005284 excitation Effects 0.000 description 31
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- 238000003756 stirring Methods 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 229910052763 palladium Inorganic materials 0.000 description 25
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- 230000006870 function Effects 0.000 description 24
- 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 24
- 238000000862 absorption spectrum Methods 0.000 description 22
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- 238000005381 potential energy Methods 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000010409 thin film Substances 0.000 description 20
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 description 19
- 238000004770 highest occupied molecular orbital Methods 0.000 description 19
- 239000011159 matrix material Substances 0.000 description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 18
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 17
- DCJKUXYSYJBBRD-UHFFFAOYSA-N 2,5-diphenyl-1,3,4-oxadiazole Chemical compound C1=CC=CC=C1C1=NN=C(C=2C=CC=CC=2)O1 DCJKUXYSYJBBRD-UHFFFAOYSA-N 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 229910045601 alloy Inorganic materials 0.000 description 17
- 239000000956 alloy Substances 0.000 description 17
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- 238000010521 absorption reaction Methods 0.000 description 16
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- 238000006243 chemical reaction Methods 0.000 description 16
- 239000002131 composite material Substances 0.000 description 16
- 150000002894 organic compounds Chemical class 0.000 description 16
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 14
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 12
- 239000003446 ligand Substances 0.000 description 12
- 239000011777 magnesium Substances 0.000 description 12
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 11
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 150000001340 alkali metals Chemical class 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 230000005281 excited state Effects 0.000 description 10
- 238000000967 suction filtration Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
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- 238000000605 extraction Methods 0.000 description 9
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- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 8
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- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 8
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 8
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 7
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- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 4
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- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
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- 150000004696 coordination complex Chemical class 0.000 description 1
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- BHQBDOOJEZXHPS-UHFFFAOYSA-N ctk3i0272 Chemical group C1=CC=CC=C1C(C(=C(C=1C=CC=CC=1)C(=C1C=2C=CC=CC=2)C=2C3=CC=CC=C3C(C=3C4=CC=CC=C4C(C=4C(=C(C=5C=CC=CC=5)C(C=5C=CC=CC=5)=C(C=5C=CC=CC=5)C=4C=4C=CC=CC=4)C=4C=CC=CC=4)=C4C=CC=CC4=3)=C3C=CC=CC3=2)C=2C=CC=CC=2)=C1C1=CC=CC=C1 BHQBDOOJEZXHPS-UHFFFAOYSA-N 0.000 description 1
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- 125000002346 iodo group Chemical group I* 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
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- 239000011733 molybdenum Substances 0.000 description 1
- WOYDRSOIBHFMGB-UHFFFAOYSA-N n,9-diphenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 WOYDRSOIBHFMGB-UHFFFAOYSA-N 0.000 description 1
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- ONDZNPJPRAIDHK-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-n-phenyl-9,9'-spirobi[fluorene]-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C2=CC=1)C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 ONDZNPJPRAIDHK-UHFFFAOYSA-N 0.000 description 1
- AJNJGJDDJIBTBP-UHFFFAOYSA-N n-(9,10-diphenylanthracen-2-yl)-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 AJNJGJDDJIBTBP-UHFFFAOYSA-N 0.000 description 1
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 1
- VZYZZKOUCVXTOJ-UHFFFAOYSA-N n-[4-[4-(n-(9,9-dimethylfluoren-2-yl)anilino)phenyl]phenyl]-9,9-dimethyl-n-phenylfluoren-2-amine Chemical group C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C(C)(C)C3=CC=CC=C3C2=CC=1)C1=CC=CC=C1 VZYZZKOUCVXTOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
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- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- HCIIFBHDBOCSAF-UHFFFAOYSA-N octaethylporphyrin Chemical compound N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 HCIIFBHDBOCSAF-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical compound C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl 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
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000008093 supporting effect Effects 0.000 description 1
- 229910001936 tantalum oxide 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
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Luminescent Compositions (AREA)
Abstract
【解決手段】電子輸送性を有する骨格とホール輸送性を有する骨格とを、共役が広がりにくいねじれたクアテルフェニレン骨格(好ましくは、[1,1’:2’,1’’:2’’,1’’’]クアテルフェニル−4−4’’’−ジイル)]基)を介して結合した材料を用いることで発光素子、発光装置、電子機器の消費電力を低減することができる。
【選択図】なし
Description
本実施の形態では、本発明の一態様である有機半導体材料について説明する。
本実施の形態では、実施の形態1で示す本発明の一態様である有機半導体材料の一例として、一般式(G1)で示した構造を有するベンゾオキサゾール誘導体について説明する。
ハロゲン化したベンゾオキサゾール化合物(化合物A)は合成スキーム(1)のようにして合成することができる。すなわちハロゲン化したベンゾオキサゾール化合物(化合物A1)とアリールボロン酸又はその誘導体を、パラジウム触媒を用いた鈴木・宮浦反応によりカップリングし、ハロゲン化したベンゾオキサゾール化合物(化合物A)を得ることができる。
ハロゲン化したベンゾオキサゾール化合物(化合物B)は合成スキーム(1−2)のようにして合成することができる。すなわちベンゾオキサゾール化合物のボロン酸またはその誘導体(化合物a1)とジハロゲン化ベンゼン(化合物a2)とを、パラジウム触媒を用いた鈴木・宮浦反応によりカップリングし、ハロゲン化したベンゾオキサゾール化合物(化合物B)を得ることができる。
ハロゲン化アリールアミン化合物(化合物B)は合成スキーム(2)のようにして合成することができる。すなわち3級アリールアミン化合物のボロン酸もしくはその誘導体(化合物B1)とジハロゲン化アリール(化合物B2)とを、パラジウム触媒を用いた鈴木・宮浦反応によりカップリングし、ハロゲン化アリールアミン化合物(化合物B)を得ることができる。合成スキーム(2)において、X1、X2はハロゲン又はトリフラート基を表し、ハロゲンとしては、ヨウ素、臭素、塩素が挙げられ、X1,X2はそれぞれ同じであっても異なっていても良い。またAr1、Ar2はそれぞれ独立に、置換又は無置換の炭素数6〜13のアリール基を表す。R94、R95は、炭素数1〜6のアルキル基を表し、R94とR95とが、互いに結合して環を形成していてもよい。
一般式(化合物C)で表される3級アリールアミンボロン酸又はその誘導体は、合成スキーム(3)のようにして合成することができる。すなわち、3級アミン化合物(化合物B)にアルキルリチウム試薬とホウ酸エステルを用いてボロン酸へ変換することにより、3級アミンボロン酸(化合物C)を得ることができる。
本実施の形態では、実施の形態1で示す本発明の一態様である有機半導体材料の一例として、一般式(G1)で示した構造を有するオキサジアゾール誘導体について説明する。
本実施の形態では、実施の形態1乃至3で示した有機半導体材料を用いた発光素子の一態様について、図1および図2を用いて説明する。
本実施の形態は、本発明の一態様に係る発光ユニットを複数積層した構成の発光素子(以下、積層型素子という)の態様について、図3を参照して説明する。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する積層型発光素子である。各発光ユニットの構成としては、上記実施の形態4で示した構成と同様な構成を用いることができる。つまり、実施の形態4で示した発光素子は、1つの発光ユニットを有する発光素子である。本実施の形態では、複数の発光ユニットを有する発光素子について説明する。
本実施の形態では、上記実施の形態で示した本発明の一態様の発光素子を有する発光装置について説明する。
本実施の形態では、実施の形態6に示す発光装置をその一部に含む本発明の一態様の電子機器について説明する。本発明の一態様の電子機器は、実施の形態4または5で示した発光素子を有し、低消費電力の表示部を有する。
まず、本実施例で用いる参照電極(Ag/Ag+電極)の真空準位に対するポテンシャルエネルギー(eV)を算出した。つまり、Ag/Ag+電極のフェルミ準位を算出した。メタノール中におけるフェロセンの酸化還元電位は、標準水素電極に対して+0.610[V vs. SHE]であることが知られている(参考文献:Christian R.Goldsmith et al., J.Am.Chem.Soc., Vol.124, No.1,83−96, 2002)。一方、本実施例で用いる参照電極を用いて、メタノール中におけるフェロセンの酸化還元電位を求めたところ、+0.11V[vs.Ag/Ag+]であった。したがって、本実施例で用いる参照電極のポテンシャルエネルギーは、標準水素電極に対して0.50[eV]低くなっていることがわかった。
まず、本測定例で、CV測定からのイオン化ポテンシャルおよび電子親和力の算出について詳述する。
また、2−フェニルベンゾオキサゾールの酸化反応特性のCV測定結果を図15に示す。なお、酸化反応特性の測定は、参照電極に対する作用電極の電位を−0.18Vから1.50Vまで走査した後、1.50Vから−0.18Vまで走査した。
また、フェニルカルバゾールの酸化反応特性のCV測定結果を図17に示す。なお、酸化反応特性の測定は、参照電極に対する作用電極の電位を−0.13Vから1.15Vまで走査した後、1.15Vから−0.13Vまで走査した。
発光素子1と同一基板を用い、Z−CzPO11の代わりに、構造式(460)で表されるZ−DPhAO11を用いて、発光素子1と同様に発光素子2を作製した。つまり、Z−DPhAO11とIr(ppy)2(acac)とを共蒸着することにより、ホール輸送層2112上に40nmの膜厚の発光層2113を形成した。ここで、Z−DPhAO11とIr(ppy)2(acac)との重量比は、1:0.06(=Z−DPhAO111:Ir(ppy)2(acac))となるように調節した。発光層2113以外は発光素子1と同様に作製した。
実施例3における発光素子1のBAlqの代わりに、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を用いて、発光素子3を作製した。つまり、Alqを10nmの膜厚となるように成膜し、第1の電子輸送層2114Aを形成した。第1の電子輸送層2114A以外は発光素子1と同様に作製した。
実施例3における発光素子1のZ−CzPO11の代わりに、構造式(101)で表されるZ−CzPBOxを用いて、発光素子1と同様に発光素子4を作製した。つまり、Z−CzPBOxとIr(ppy)2(acac)とを共蒸着することにより、ホール輸送層2112上に40nmの膜厚の発光層2113を形成した。ここで、Z−CzPBOxとIr(ppy)2(acac)との重量比は、1:0.06(=Z−CzPBOx:Ir(ppy)2(acac))となるように調節した。発光層2113以外は発光素子1と同様に作製した。
発光素子4と同一基板を用い、Z−CzPBOxの代わりに、構造式(201)で表されるZ−DPhABOxを用いて、発光素子4と同様に発光素子5を作製した。つまり、Z−DPhABOxとIr(ppy)2(acac)とを共蒸着することにより、ホール輸送層2112上に40nmの膜厚の発光層2113を形成した。ここで、Z−DPhABOxとIr(ppy)2(acac)との重量比は、1:0.06(=Z−DPhABOx:Ir(ppy)2(acac))となるように調節した。発光層2113以外は発光素子4と同様に作製した。
実施例5における発光素子4のBAlqの代わりに、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を用いて、発光素子6を作製した。つまり、Alqを10nmの膜厚となるように成膜し、第1の電子輸送層2114Aを形成した。第1の電子輸送層2114A以外は発光素子4と同様に作製した。
実施の形態3で示すオキサジアゾール誘導体の一である、構造式(421)で表される9−[4’’’−(5−フェニル−1,3,4−オキサジアゾール−2−イル)−[1,1’:2’,1’’:2’’,1’’’]クアテルフェニル−4−イル)]−9H−カルバゾール(略称:Z−CzPO11)の合成方法について説明する。
4−ヨードベンゾイルヒドラジンの合成スキームを(A−1)に示す。
1−ベンゾイル−2−(4−ヨードベンゾイル)ヒドラジンの合成スキームを(A−2)に示す。
2−(4−ヨードフェニル)−5−フェニル−1,3,4−オキサジアゾール
ンの合成スキームを(A−3)に示す。
2−(2’−ブロモビフェニル−4−イル)−5−フェニル−1,3,4−オキサジアゾールの合成スキームを(A−4)に示す。
9−(2’−ブロモビフェニル−4−イル)−9H−カルバゾールの合成スキームを(B−1)に示す。
4’−(9H−カルバゾール−9−イル)ビフェニル−2−ボロン酸の合成スキームを(B−2)に示す。
Z−CzPO11の合成スキームを(E−1)に示す。
1H NMR(CDCl3,300MHz):δ=6.79(d,J=8.3Hz,2H)、6.88(d,J=8.3Hz,2H)、7.22(d,J=8.3Hz,2H)、7.25−7.33(m,4H)、7.39−7.62(m,13H)、7.84(d,J=8.3Hz,2H)、8.09−8.18(m,4H)
実施の形態3で示すオキサジアゾール誘導体の一である、構造式(460)で表される4−[4’’−(5−フェニル−1,3,4,−オキサジアゾール−2−イル)−[1,1’:2’,1’’]テルフェニル−2−イル]トリフェニルアミン(略称:Z−DPhAO11)の合成方法について説明する。
4−(ジフェニルアミノ)フェニルボロン酸の合成スキームを(C−1)に示す。
4−(2’−ブロモフェニル)トリフェニルアミンの合成スキームを(C−2)に示す。
4’−(ジフェニルアミノ)ビフェニル−2−ボロン酸の合成スキームを(C−3)に示す。
Z−DPhAO11の合成スキームを(E−2)に示す。
1H NMR(CDCl3,300MHz):δ=6.44(d,J=8.8Hz,2H)、6.72(d,J=8.8Hz,2H)、6.86(d,J=8.8Hz,2H)、6.97−7.56(m,21H)、7.79(d,J=8.3Hz,2H)、8.09−8.13(m,2H)
実施の形態2で示すベンゾオキサゾール誘導体の一である、構造式(101)で表される9−[4’’’−(ベンゾオキサゾール−2−イル)−[1,1’:2’,1’’:2’’,1’’’]クアテルフェニル−4−イル)]−9H−カルバゾール(略称:Z−CzPBOx)の合成方法について説明する。
4−ヨードベンゾイルクロリドの合成スキームを(D−1)に示す。
4−ヨード−N−(2−ヒドロキシフェニル)ベンズアミドの合成スキームを(D−2)に示す。
2−(4−ヨードフェニル)ベンゾオキサゾールの合成スキームを(D−3)に示す。
2−(2’−ブロモビフェニル−4−イル)ベンゾオキサゾールの合成スキームを(D−4)に示す。
Z−CzPBOxの合成スキームを(E−3)に示す。
1H NMR(CDCl3,300MHz):δ=6.78(d,J=8.3Hz,2H)、6.87(d,J=8.3Hz,2H)、7.15−7.62(m,19H)、7.72−7.77(m,1H)、7.95(d,J=8.3Hz,2H)、8.16(d,J=7.8Hz,2H)。
実施の形態2で示すベンゾオキサゾール誘導体の一である、構造式(201)で表される4−[4’’−(ベンゾオキサゾール−2−イル)−[1,1’:2’,1’’]クアテルフェニル−2−イル]トリフェニルアミン(略称:Z−DPhABOx)の合成方法について説明する。
Z−DPhABOxの合成スキームを(E−4)に示す。
1H NMR(CDCl3,300MHz):δ=6.45(d,J=8.3Hz,2H)、6.71(d,J=8.3Hz,2H)、6.85(d,J=8.3Hz,2H)、6.98−7.17(m,7H)、7.23−7.57(m,14H)、7.71−7.75(m,1H)、7.92(d,J=7.8Hz,2H)。
102 第1の電極
103 EL層
104 第2の電極
111 ホール注入層
112 ホール輸送層
113 発光層
114 電子輸送層
115 電子注入層
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 ソース側駆動回路
602 画素部
603 ゲート側駆動回路
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 第1の電極
614 絶縁物
616 EL層
617 第2の電極
618 発光素子
623 Nチャネル型TFT
624 Pチャネル型TFT
701 本体
702 表示部
703 操作スイッチ
704 表示部
710 本体
711 表示部
712 メモリ部
713 操作部
714 イヤホン
901 筐体
902 液晶層
903 バックライト
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 EL層
956 電極
1001 筐体
1002 筐体
1101 表示部
1102 スピーカー
1103 マイクロフォン
1104 操作キー
1105 ポインティングデバイス
1106 カメラ用レンズ
1107 外部接続端子
1108 イヤホン端子
1201 キーボード
1202 外部メモリスロット
1203 カメラ用レンズ
1204 ライト
2001 筐体
2002 光源
2101 ガラス基板
2102 第1の電極
2104 第2の電極
2111 複合材料を含む層
2112 ホール輸送層
2113 発光層
2114A 第1の電子輸送層
2114B 第2の電子輸送層
2115 電子注入層
3001 照明装置
3002 テレビ装置
9101 筐体
9102 支持台
9103 表示部
9104 スピーカー部
9105 ビデオ入力端子
9201 本体
9202 筐体
9203 表示部
9204 キーボード
9205 外部接続ポート
9206 ポインティングデバイス
9301 本体
9302 表示部
9303 筐体
9304 外部接続ポート
9305 リモコン受信部
9306 受像部
9307 バッテリー
9308 音声入力部
9309 操作キー
9310 接眼部
9401 本体
9402 筐体
9403 表示部
9404 音声入力部
9405 音声出力部
9406 操作キー
9407 外部接続ポート
9408 アンテナ
Claims (20)
- 一般式(G1)で表される有機半導体材料。
(式中、EAは電子受容ユニット、HAはホール受容ユニットであり、α1の炭素とEAは結合して環を形成していてもよく、α2の炭素とHAは結合して環を形成していてもよい。) - 一般式(G1)で表される有機半導体材料。
(式中、EAおよびHAは、それぞれ置換基であり、α1の炭素とEAは結合して環を形成していてもよく、α2の炭素とHAは結合して環を形成していてもよい。また、aで表される骨格を水素で置換した一般式(G2A)で表される化合物は、bで表される骨格を水素で置換した一般式(G2B)で表される化合物よりも、電子親和力が大きく、かつ、イオン化ポテンシャルが大きい。) - 請求項2において、
一般式(G2A)で表される化合物の電子親和力は2.0eV以上4.0eV以下であり、一般式(G2B)で表される化合物のイオン化ポテンシャルは4.5eV以上6.5eV以下であることを特徴とする有機半導体材料。 - 請求項2において、
一般式(G2A)で表される化合物の電子親和力は2.0eV以上3.0eV以下であり、一般式(G2B)で表される化合物のイオン化ポテンシャルは5.0eV以上6.0eV以下であることを特徴とする有機半導体材料。 - 請求項1乃至請求項4のいずれか一項において、
前記EAは、含窒素6員芳香環基、1,2−アゾール基、1,3−アゾール基、ポリアゾール基のいずれか一である有機半導体材料。 - 請求項1乃至請求項5のいずれか一項において、
前記HAはπ過剰系ヘテロ芳香族置換基、またはジアリールアミノ基である有機半導体材料。 - 一対の電極間に、請求項1乃至請求項6のいずれか一項に記載の有機半導体材料を含む発光素子。
- 一般式(BOX1)で表されるベンゾオキサゾール誘導体。
(式中、Ar1、Ar2は、それぞれ独立に、置換又は無置換の炭素数6〜13のアリール基を表し、R1〜R4は、それぞれ独立に、水素、炭素数1〜4のアルキル基、無置換の炭素数6〜10のアリール基、ハロゲンのいずれかを表す。Ar1とαの炭素、又はAr1とAr2とは、直接、又は硫黄、酸素、もしくは窒素を介して結合していてもよい。) - 一般式(BOX2)で表されるベンゾオキサゾール誘導体。
(式中、R1〜R4は、それぞれ独立に、水素、炭素数1〜4のアルキル基、無置換の炭素数6〜10のアリール基、ハロゲンのいずれかを表し、R11〜R20は、それぞれ独立に、水素、炭素数1〜4のアルキル基、置換又は無置換の炭素数6〜13のアリール基のいずれかを表す。R11とαの炭素、又はR15とR20とは、直接結合していてもよい。) - 一般式(BOX2)で表されるベンゾオキサゾール誘導体。
(式中、R1〜R4は、それぞれ独立に、水素、炭素数1〜4のアルキル基、無置換の炭素数6〜10のアリール基、ハロゲンのいずれかを表し、R11〜R20は、それぞれ独立に、水素、炭素数1〜4のアルキル基、置換又は無置換の炭素数6〜13のアリール基のいずれかを表す。R11とαの炭素、又はR15とR20とは、直接結合してカルバゾール骨格を形成してもよい。) - 一般式(BOX3)で表されるベンゾオキサゾール誘導体。
(式中、R11〜R20は、それぞれ独立に、水素、炭素数1〜4のアルキル基、置換又は無置換の炭素数6〜13のアリール基のいずれかを表す。R11とαの炭素、又はR15とR20とは、直接結合してカルバゾール骨格を形成してもよい。) - 請求項8乃至11のいずれか一項に記載のベンゾオキサゾール誘導体を用いた発光素子。
- 一般式(OXD1)で表されるオキサジアゾール誘導体。
(式中、Ar11、Ar12及びAr13は、炭素数6〜13の置換または無置換のアリール基を表す。また、Ar11とαの炭素、又は、Ar11とAr12は、それぞれ互いに直接結合していてもよく、あるいは、酸素、硫黄、又は窒素のいずれかを介して結合していてもよい。) - 一般式(OXD2)で表されるオキサジアゾール誘導体。
(式中、R31〜R40は、水素、炭素数1〜4のアルキル基、又は炭素数6〜13の無置換のアリール基のいずれかを表し、Ar13は、炭素数6〜13の置換又は無置換のアリール基を表す。また、R31とαの炭素、又は、R35とR40は、それぞれ互いに結合してカルバゾール骨格を形成していてもよい。) - 一般式(OXD2)で表されるオキサジアゾール誘導体。
(式中、R31〜R40は、水素、炭素数1〜4のアルキル基、又は炭素数6〜13の無置換のアリール基のいずれかを表し、Ar13は、置換又は無置換のフェニル基、置換又は無置換のナフチル基のいずれかを表す。) - 一般式(OXD2)で表されるオキサジアゾール誘導体。
(式中、R31〜R40は、水素、炭素数1〜4のアルキル基、又は炭素数6〜13の無置換のアリール基のいずれかを表し、Ar13は、無置換のフェニル基、または、無置換の1−ナフチル基、または無置換の2−ナフチル基のいずれかを表す。) - 請求項1乃至請求項4のいずれか一に記載のオキサジアゾール誘導体を用いた発光素子。
- 請求項7、請求項12または請求項17のいずれか一項に記載の発光素子を有する発光装置。
- 請求項18に記載の発光装置を用いた照明装置。
- 表示部を有し、
前記表示部は、請求項18に記載の発光装置を備えた電子機器。
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US10243151B2 (en) | 2019-03-26 |
JP2015128166A (ja) | 2015-07-09 |
US20100060155A1 (en) | 2010-03-11 |
KR20140107700A (ko) | 2014-09-04 |
KR101549878B1 (ko) | 2015-09-03 |
JP2019135768A (ja) | 2019-08-15 |
EP2321862A4 (en) | 2013-03-13 |
JP2018111709A (ja) | 2018-07-19 |
JP6496857B2 (ja) | 2019-04-10 |
MY150594A (en) | 2014-01-30 |
JP6831866B2 (ja) | 2021-02-17 |
WO2010027004A1 (en) | 2010-03-11 |
US8343639B2 (en) | 2013-01-01 |
CN102144313A (zh) | 2011-08-03 |
JP2017041647A (ja) | 2017-02-23 |
JP2014058527A (ja) | 2014-04-03 |
US20130112961A1 (en) | 2013-05-09 |
EP2321862B1 (en) | 2014-11-19 |
KR20110063749A (ko) | 2011-06-14 |
CN102144313B (zh) | 2014-07-30 |
US9620723B2 (en) | 2017-04-11 |
EP2321862A1 (en) | 2011-05-18 |
JP6306663B2 (ja) | 2018-04-04 |
US20170250352A1 (en) | 2017-08-31 |
JP5693692B2 (ja) | 2015-04-01 |
KR101529062B1 (ko) | 2015-06-16 |
JP5399173B2 (ja) | 2014-01-29 |
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