JP2009167173A - トリアゾール誘導体およびトリアゾール誘導体を用いた発光素子、発光装置、電子機器 - Google Patents
トリアゾール誘導体およびトリアゾール誘導体を用いた発光素子、発光装置、電子機器 Download PDFInfo
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- JP2009167173A JP2009167173A JP2008317223A JP2008317223A JP2009167173A JP 2009167173 A JP2009167173 A JP 2009167173A JP 2008317223 A JP2008317223 A JP 2008317223A JP 2008317223 A JP2008317223 A JP 2008317223A JP 2009167173 A JP2009167173 A JP 2009167173A
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- carbon atoms
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- light
- aryl group
- triazole derivative
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- 150000003852 triazoles Chemical class 0.000 title claims abstract description 128
- 239000000126 substance Substances 0.000 claims abstract description 104
- 125000004432 carbon atom Chemical group C* 0.000 claims description 251
- 125000003118 aryl group Chemical group 0.000 claims description 115
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 31
- 125000000732 arylene group Chemical group 0.000 claims description 27
- 229910052799 carbon Inorganic materials 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 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000005284 excitation Effects 0.000 abstract description 55
- 239000010410 layer Substances 0.000 description 204
- 230000015572 biosynthetic process Effects 0.000 description 81
- 238000003786 synthesis reaction Methods 0.000 description 81
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- 238000000034 method Methods 0.000 description 67
- 150000001875 compounds Chemical class 0.000 description 65
- -1 4-tert-butylphenyl group Chemical group 0.000 description 51
- 239000007787 solid Substances 0.000 description 46
- 239000000463 material Substances 0.000 description 43
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 150000002894 organic compounds Chemical class 0.000 description 30
- 239000000758 substrate Substances 0.000 description 29
- 239000010408 film Substances 0.000 description 27
- 230000005525 hole transport Effects 0.000 description 27
- 238000002347 injection Methods 0.000 description 27
- 239000007924 injection Substances 0.000 description 27
- 239000000203 mixture Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000002131 composite material Substances 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
- 235000019341 magnesium sulphate Nutrition 0.000 description 16
- 0 *c(cc1)cc2c1[n](Cc1cc(N(c(cc3)ccc3-c([n]3[Al])nnc3[Al]=C)[Al])ccc1)c1ccc(*)cc21 Chemical compound *c(cc1)cc2c1[n](Cc1cc(N(c(cc3)ccc3-c([n]3[Al])nnc3[Al]=C)[Al])ccc1)c1ccc(*)cc21 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000000862 absorption spectrum Methods 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 12
- 239000010409 thin film 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 11
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 11
- 230000005281 excited state Effects 0.000 description 11
- 239000011159 matrix material Substances 0.000 description 11
- 238000003775 Density Functional Theory Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000004364 calculation method Methods 0.000 description 10
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 10
- 238000000295 emission spectrum Methods 0.000 description 10
- 239000007850 fluorescent dye Substances 0.000 description 10
- 150000007857 hydrazones Chemical class 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 238000004544 sputter deposition Methods 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
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- 125000005549 heteroarylene group Chemical group 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 8
- 150000004706 metal oxides Chemical class 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000000967 suction filtration Methods 0.000 description 8
- 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 8
- 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 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 239000000956 alloy Substances 0.000 description 7
- 229910045601 alloy Inorganic materials 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 229910003437 indium oxide Inorganic materials 0.000 description 7
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 239000010453 quartz Substances 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- 238000001308 synthesis method Methods 0.000 description 7
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [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 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 6
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000005749 Copper compound Substances 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 238000006887 Ullmann reaction Methods 0.000 description 6
- 150000001716 carbazoles Chemical class 0.000 description 6
- 150000001880 copper compounds Chemical class 0.000 description 6
- 230000005283 ground state Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000003335 secondary amines Chemical class 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- 229910001930 tungsten oxide Inorganic materials 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 230000001413 cellular effect Effects 0.000 description 5
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- 125000002346 iodo group Chemical group I* 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 239000003566 sealing material Substances 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 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 5
- 239000011787 zinc oxide Substances 0.000 description 5
- 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 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 4
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000000412 dendrimer Substances 0.000 description 4
- 229920000736 dendritic polymer Polymers 0.000 description 4
- 125000005077 diacylhydrazine group Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 229910052814 silicon oxide Inorganic materials 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- GRRIYLZJLGTQJX-UHFFFAOYSA-N 1,2-dibenzoylhydrazine Chemical compound C=1C=CC=CC=1C(=O)NNC(=O)C1=CC=CC=C1 GRRIYLZJLGTQJX-UHFFFAOYSA-N 0.000 description 3
- UYROTQZLUVRLJT-UHFFFAOYSA-N 4-(4-bromophenyl)-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC(Br)=CC=C1N1C(C=2C=CC=CC=2)=NN=C1C1=CC=CC=C1 UYROTQZLUVRLJT-UHFFFAOYSA-N 0.000 description 3
- UYIMBYKIIMYFPS-UHFFFAOYSA-N 4-bromobenzohydrazide Chemical compound NNC(=O)C1=CC=C(Br)C=C1 UYIMBYKIIMYFPS-UHFFFAOYSA-N 0.000 description 3
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 3
- XSDKKRKTDZMKCH-UHFFFAOYSA-N 9-(4-bromophenyl)carbazole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 XSDKKRKTDZMKCH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 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
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 3
- 229910052761 rare earth metal Inorganic materials 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 229910001935 vanadium oxide Inorganic materials 0.000 description 3
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- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
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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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
本実施の形態1では、本発明のトリアゾール誘導体について説明する。
<ハロゲン化トリアゾール誘導体(TAZ−1)の合成法>
ハロゲン化トリアゾール誘導体(TAZ−1)の合成スキームを(A−1)に示す。
ハロゲン化トリアゾール誘導体(TAZ−2)の合成スキームを(A−2)に示す。
上述の一般式(G2)で表される2級アミンは、下記合成スキーム(B−1)のようにして合成することができる。すなわち、まずジハロゲン化アレーン(化合物A3)とカルバゾール誘導体(化合物B3)とを、塩基存在下にて金属触媒を用いてカップリングさせることにより、ハロゲン化アリールカルバゾール誘導体(化合物C3)を合成する。次に、ハロゲン化アリールカルバゾール誘導体(化合物C3)とアリールアミン(化合物D3)とを、塩基存在下にて金属触媒を用いてカップリングさせることにより2級アミン(Am−1)を得ることができる。
上述の合成スキーム(A−1)で得られたハロゲン化トリアゾール誘導体(TAZ−1)または合成スキーム(A−2)で得られたハロゲン化トリアゾール誘導体(TAZ−2)のいずれかと、2級アミン誘導体(Am−1)とを塩基存在下にて金属触媒を用いてカップリングさせることにより、本発明のトリアゾール誘導体が得られる。合成スキーム(C−1)および(C−2)に示す。
本実施の形態2では、本発明のトリアゾール誘導体を用いた発光素子の一態様について図1を用いて説明する。
本実施の形態3では、実施形態2で示した構成と異なる構成の発光素子について説明する。
本実施の形態は、本発明に係る複数の発光ユニットを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2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、実施の形態2および実施の形態3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2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、本発明のトリアゾール誘導体を用いて作製された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5に示す発光装置をその一部に含む本発明の電子機器について説明する。本発明の電子機器は、実施の形態1に示したトリアゾール誘導体を含み、発光効率の高い表示部を有する。また、消費電力の低減された表示部を有する。
本実施例では、構造式(200)で表される4−(9H−カルバゾール−9−イル)−4’−(4,5−ジフェニル−4H−1,2,4−トリアゾール−3−イル)トリフェニルアミン(略称:YGATAZ1)の合成方法について説明する。
(1)4−ブロモベンゾイルヒドラジンの合成。
エチル−4−ブロモベンゾエート25g(0.19mol)を200mL三口フラスコに入れ、エタノール50mLを加えて撹拌した後、ヒドラジン一水和物20mLを加え,この混合物を78℃で5時間加熱撹拌し、反応させた。反応後、反応混合物に水を加え、析出した固体を吸引ろ過により回収した。得られた固体を水で洗浄し、吸引ろ過により回収したところ、目的物である4−ブロモベンゾイルヒドラジンの白色固体を収量24g、収率96%で得た。(合成スキーム(a−1))
上記ステップ1(1)で得られた4−ブロモベンゾイルヒドラジン2.0g(13.9mmol)を300mL三口フラスコに入れ、N−メチル−2−ピロリドン7mlを加え、室温で撹拌した。この溶液にN−メチル−2−ピロリドン5.0mLとベンゾイルクロライド2.5mL(21.5mmol)の混合溶液を50mL滴下ロートにより滴下した。この混合物を80℃で3時間撹拌した。反応後、反応混合物を約200mLの水に加えたところ、固体が析出した。析出した固体を吸引ろ過により回収した。回収した固体を水、飽和炭酸水素ナトリウム水溶液、飽和食塩水の順に洗浄して得た固体をアセトンとヘキサンの混合溶媒で再結晶したところ、目的物であるN’−ベンゾイル−4−ブロモ−ベンゾヒドラジドの白色固体を収量3.6g、収率80%で得た。(合成スキーム(a−2))
上記ステップ1(2)で得られたN’−ベンゾイル−4−ブロモ−ベンゾヒドラジド5.0g(16mmol),五塩化リン7.2g(34mmol)を200mL三口フラスコに入れ、この混合物にトルエン100mLを加えた。この混合物を120℃で3時間撹拌し、反応させた。反応後、反応溶液を約100mLの水に加えて撹拌した。有機層と水層を分離し、有機層を飽和炭酸ナトリウム水溶液、飽和食塩水で洗浄した。有機層に硫酸マグネシウムを加えて乾燥した。この混合物を吸引ろ過して硫酸マグネシウムを除去し、ろ液を得た。得られたろ液を濃縮して得た固体をメタノールで洗浄したところ、目的物である1−[(4−ブロモフェニル)クロロメチリデン]−2−[クロロ(フェニル)メチリデン]ヒドラゾンの粉末状淡黄色固体を収量4.8g、収率86%で得た。(合成スキーム(a−3))
上記ステップ1(3)で得られた1−[(4−ブロモフェニル)クロロメチリデン]−2−[クロロ(フェニル)メチリデン]ヒドラゾン4.5g(16mmol)、アニリン2.0g(16mmol)、N,N−ジメチルアニリン30mLを100mL三口フラスコに入れ、当該フラスコ内を窒素置換した。この混合物を135℃で5時間加熱撹拌した。反応後、反応溶液を約100mLの1M希塩酸に加えて30分撹拌したところ、固体が析出した。析出した固体を吸引ろ過して固体を得た。得られた固体をトルエンに溶解し水、飽和炭酸ナトリウム水溶液で洗浄した。有機層に硫酸マグネシウムを加えて乾燥した。この混合物を吸引ろ過し、硫酸マグネシウムを除去し、ろ液を得た。得られたろ液を濃縮して得た固体をエタノールとヘキサンの混合溶媒で再結晶したところ、目的物である3−(4−ブロモフェニル)−4,5−ジフェニル−4H−1,2,4−トリアゾールの粉末状淡黄色固体を収量3.3g、収率69%で得た。(合成スキーム(a−4))
(1)9−(4−ブロモフェニル)−9H−カルバゾールの合成。
p−ジブロモベンゼン56g(240mmol)、9H−カルバゾール 31g(180mmol)、ヨウ化銅(I)4.6g(24mmol)、炭酸カリウム66g(480mmol)、18−クラウン−6−エーテル2.1g(8mmol)を300mL三口フラスコに入れて窒素置換し、N,N’−ジメチルプロピレンウレア(略称:DMPU)8mLを加え、180℃で6時間撹拌した。反応混合物を室温まで冷ましてから、吸引ろ過により沈殿物を除去した。ろ液を希塩酸、飽和炭酸水素ナトリウム水溶液、飽和食塩水の順で洗浄した後、硫酸マグネシウムにより乾燥した。乾燥後、混合物を自然ろ過してから濃縮し、得られた油状物質をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=9:1)により精製し、クロロホルムとヘキサンにより再結晶したところ、目的物である9−(4−ブロモフェニル)−9H−カルバゾールの淡褐色プレート状結晶を収量21g、収率35%で得た。(合成スキーム(a−5))
上記ステップ2(1)で得られた9−(4−ブロモフェニル)−9H−カルバゾール5.4g(17mmol)、アニリン1.8mL(20mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)0.1g(0.2mmol)、ナトリウム tert−ブトキシド3.9g(40mmol)を200mL三口フラスコに入れて窒素置換し、トリ(tert−ブチル)ホスフィンの10%ヘキサン溶液0.1mLおよびトルエン50mLを加え、80℃で6時間撹拌した。反応混合物をフロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、セライト(和光純薬工業株式会社、カタログ番号:531−16855)、アルミナを通してろ過し、ろ液を水、飽和食塩水で洗浄後、硫酸マグネシウムで乾燥した。乾燥後、混合物を自然ろ過し、得られたろ液を濃縮し、得られた油状物をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=9:1)により精製したところ、本ステップ2の目的物である4−(9H−カルバゾール−9−イル)ジフェニルアミン(略称:YGA)を収量4.1g、収率73%で得た。合成スキーム(a−6))
上記ステップ1(1)〜(4)で得られた3−(4−ブロモフェニル)−4,5−ジフェニル−4H−1,2,4−トリアゾール1.5g(4.0mmol)、上記ステップ2(1)〜(2)で得られた4−(9H−カルバゾール−9−イル)ジフェニルアミン(略称:YGA)1.3g(4.0mmol)、ナトリウム tert−ブトキシド1.0g(11mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)0.1g(0.2mmol)を100mL三口フラスコに入れ、当該フラスコ内を窒素置換した。この混合物にトルエン30mL、トリ(tert−ブチル)ホスフィンの10%ヘキサン溶液0.1mLを加えた。この混合物を80℃で5時間加熱攪拌し反応させた。反応後、反応混合物にトルエンを加えて加熱した。この懸濁液をセライト(和光純薬工業株式会社、カタログ番号:531−16855)を通して吸引ろ過した。得られたろ液を水、飽和炭酸水素ナトリウム水溶液、飽和食塩水の順で洗浄した後、有機層と水層を分離し、有機層に硫酸マグネシウムを加えて乾燥した。この混合物を吸引ろ過し、硫酸マグネシウムを除去して得られたろ液を濃縮し固体を得た。得られた固体をトルエンに溶解し、シリカゲルカラムクロマトグラフィーにより精製した。カラムクロマトグラフィーはまずトルエンを展開溶媒として用い、次いでトルエン:酢酸エチル=1:4の混合溶媒を展開溶媒として用いた。得られたフラクションを濃縮し、固体を得た。得られた固体をクロロホルムとヘキサンの混合溶媒で再結晶をしたところ、目的物である4−(9H−カルバゾール−9−イル)−4’−(4,5−ジフェニル−4H−1,2,4−トリアゾール−3−イル)トリフェニルアミン(略称:YGATAZ1)の白色固体を収量1.8g、収率72%で得た。(合成スキーム(a−7))
本実施例では、構造式(201)で表される4−(9H−カルバゾール−9−イル)−4’−(3,5−ジフェニル−4H−1,2,4−トリアゾール−4−イル)トリフェニルアミン((略称:YGATAZ2)の合成方法について説明する。
安息香酸エチル25g(0.17mol)を200mL三口フラスコに入れ、エタノール60mLを加えて撹拌した後、ヒドラジン一水和物20mLを加え、この混合物を78℃で8時間加熱撹拌した。反応後、反応溶液を約500mLの水に加え、この水溶液に酢酸エチルを加えた。有機層と水層を分離し有機層を飽和炭酸水素ナトリウム水溶液、飽和食塩水の順に洗浄した。有機層に硫酸マグネシウムを加えて乾燥した。この混合物を吸引ろ過して硫酸マグネシウムを除去し、ろ液を得た。得られたろ液を濃縮して得た固体をエタノールとヘキサンの混合溶媒で再結晶したところ、目的物であるベンゾヒドラジドの白色固体を収量15g、収率66%で得た。(合成スキーム(b−1))
上記合成例2のステップ1(1)で得られたベンゾヒドラジド10g(73mmol)を300mL三口フラスコに入れ、N−メチル−2−ピロリドン25mLを加え撹拌した後、N−メチル−2−ピロリドン10mLとベンゾイルクロライド10mL(88mmol)の混合溶液を50mL滴下ロートにより滴下し、この混合物を80℃で3時間撹拌し、反応させた。反応後、反応溶液を約500mLの水に加えて撹拌したところ固体が析出した。析出した固体を吸引ろ過により回収した。回収した固体を水で洗浄し、得られた固体にメタノールを加えて洗浄したところ目的物である1,2−ジベンゾイルヒドラジンの粉末状白色固体を収量10g、収率57%で得た。合成スキーム(b−2))
上記合成例2のステップ1(2)で得られた1,2−ジベンゾイルヒドラジン5.0g(21mmol),五塩化リン9.5g(46mmol)を200mL三口フラスコに入れ、この混合物にトルエン80mLを加えた。この混合物を120℃で3時間撹拌し、反応させた。反応後、反応溶液を約100mLの水に加えて撹拌した。有機層と水層を分離し、有機層を水、飽和炭酸ナトリウム水溶液で洗浄した。有機層に硫酸マグネシウムを加えて乾燥した。この混合物を吸引ろ過により硫酸マグネシウムを除去し、ろ液を得た。得られたろ液を濃縮して得た固体をメタノールで洗浄したところ目的物である1,2−ビス[クロロ(フェニル)メチリデン]ヒドラゾンの粉末状淡黄色固体を収量4.9g、収率85%で得た。合成スキーム(b−3))
上記合成例2のステップ1(3)で得られた1,2−ビス(クロロ(フェニル)メチリデン)ヒドラゾン4.5g(16mmol)、4−ブロモアニリン2.0g(16mmol)、N,N−ジメチルアニリン30mLを100mL三口フラスコに入れ、フラスコ内を窒素置換した。この混合物を135℃で5時間加熱撹拌した。反応後、反応溶液を約100mLの1M希塩酸に加えて30分撹拌したところ固体が析出した。析出した固体を吸引ろ過して固体を得た。得られた固体をトルエンに溶解し水、飽和炭酸ナトリウム水溶液で洗浄した。有機層に硫酸マグネシウムを加えて乾燥した。この混合物を吸引ろ過し、硫酸マグネシウムを除去し、ろ液を得た。得られたろ液を濃縮して得た固体をエタノールとヘキサンの混合溶媒で再結晶したところ、目的物である4−(4−ブロモフェニル)−3,5−ジフェニル−4H−1,2,4−トリアゾールの粉末状白色固体を収量2.3g、収率38%で得た。(合成スキーム(b−4))
上記合成例2のステップ1(1)〜(4)で得られた4−(4−ブロモフェニル)−3,5−ジフェニル−4H−1,2,4−トリアゾール0.80g(2.1mmol)、上記合成例1のステップ2(1)〜(2)で得られた4−(9H−カルバゾール−9−イル)ジフェニルアミン(略称:YGA)0.71g(2.1mmol)、ナトリウム tert−ブトキシド0.5g(5.5mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)0.050g(0.10mmol)を100mL三口フラスコに入れ、当該フラスコ内を窒素置換した。この混合物にトルエン15mL、トリ(tert−ブチル)ホスフィンの10%ヘキサン溶液0.05mLを加えた。この混合物を80℃で5時間加熱攪拌し、反応させた。反応後、反応混合物にトルエンを加えて加熱した。この懸濁液をセライト(和光純薬工業株式会社、カタログ番号:531−16855)を通して吸引ろ過した。得られたろ液を水、飽和炭酸水素ナトリウム水溶液、飽和食塩水の順で洗浄した後、有機層と水層を分離し、有機層に硫酸マグネシウムを加えて乾燥した。この混合物を吸引ろ過し、硫酸マグネシウムを除去して得られたろ液を濃縮し固体を得た。得られた固体をトルエンに溶解し、シリカゲルカラムクロマトグラフィーにより精製した。カラムクロマトグラフィーはまずトルエンを展開溶媒として用い、次いでトルエン:酢酸エチル=1:4の混合溶媒を展開溶媒として用いた。得られたフラクションを濃縮し、固体を得た。得られた固体をクロロホルムとヘキサンの混合溶媒で再結晶をしたところ目的物である4−(9H−カルバゾール−9−イル)−4’−(3,5−ジフェニル−4H−1,2,4−トリアゾール−4−イル)トリフェニルアミン(略称:YGATAZ2)を収量0.85g、収率64%で得た。(合成スキーム(b−5))
101 第1の電極
102 第2の電極
103 有機化合物を含む層
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
401 駆動回路(ソース側駆動回路)
402 画素部
403 駆動回路(ゲート側駆動回路)
404 封止基板
405 シール材
407 空間
408 配線
409 FPC(フレキシブルプリントサーキット)
410 素子基板
411 スイッチング用TFT
412 電流制御用TFT
413 第1の電極
414 絶縁物
416 有機化合物を含む層
417 第2の電極
418 発光素子
423 nチャネル型TFT
424 pチャネル型TFT
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
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
2001 筐体
2002 光源
2100 ガラス基板
2101 第1の電極
2102 第2の電極
2111 複合材料を含む層
2112 正孔輸送層
2113 発光層
2114 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
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
9501 本体
9502 表示部
9503 筐体
9504 外部接続ポート
9505 リモコン受信部
9506 受像部
9507 バッテリー
9508 音声入力部
9509 操作キー
9510 接眼部
Claims (18)
- 請求項2乃至請求項6のいずれか一項において、前記Ar1および前記Ar2は、それぞれフェニル基またはピリジル基であるトリアゾール誘導体。
- 請求項8乃至請求項12のいずれか一項において、前記Ar1および前記Ar3は、それぞれフェニル基またはピリジル基であるトリアゾール誘導体。
- 一対の電極間に、請求項1乃至請求項13のいずれか一項に記載のトリアゾール誘導体を有することを特徴とする発光素子。
- 一対の電極間に発光層を有し、当該発光層は請求項1乃至請求項13のいずれか一項に記載のトリアゾール誘導体を有することを特徴とする発光素子。
- 一対の電極間に発光層を有し、当該発光層は請求項1乃至請求項13のいずれか一項に記載のトリアゾール誘導体と、燐光を発光する物質とを有することを特徴とする発光素子。
- 請求項14乃至請求項16のいずれか一項に記載の発光素子と、当該発光素子の発光を制御する制御回路を有する発光装置。
- 表示部を有し、当該表示部は請求項14乃至請求項16のいずれか一項に記載の発光素子と当該発光素子の発光を制御する制御回路とを備えたことを特徴とする電子機器。
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US9806268B2 (en) | 2010-05-21 | 2017-10-31 | Semiconductor Energy Laboratory Co., Ltd. | Triazole derivative, and light-emitting element, light-emitting device, electronic device and lighting device using the triazole derivative |
US9273079B2 (en) | 2011-06-29 | 2016-03-01 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device |
JP2014140027A (ja) * | 2012-12-20 | 2014-07-31 | Semiconductor Energy Lab Co Ltd | 発光素子、発光装置、電子機器、及び照明装置 |
US9741946B2 (en) | 2012-12-20 | 2017-08-22 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element containing organic iridium exhibits blue-green to blue light emission |
Also Published As
Publication number | Publication date |
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EP2229382B1 (en) | 2012-07-18 |
KR101563675B1 (ko) | 2015-10-27 |
US20090160324A1 (en) | 2009-06-25 |
JP2014037421A (ja) | 2014-02-27 |
EP2229382A4 (en) | 2011-05-04 |
US8906518B2 (en) | 2014-12-09 |
KR20100101668A (ko) | 2010-09-17 |
JP5650824B2 (ja) | 2015-01-07 |
WO2009081718A1 (en) | 2009-07-02 |
EP2229382A1 (en) | 2010-09-22 |
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