JP5297167B2 - キノキサリン誘導体、およびキノキサリン誘導体を用いた発光素子、発光装置並びに電子機器 - Google Patents
キノキサリン誘導体、およびキノキサリン誘導体を用いた発光素子、発光装置並びに電子機器 Download PDFInfo
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- JP5297167B2 JP5297167B2 JP2008304456A JP2008304456A JP5297167B2 JP 5297167 B2 JP5297167 B2 JP 5297167B2 JP 2008304456 A JP2008304456 A JP 2008304456A JP 2008304456 A JP2008304456 A JP 2008304456A JP 5297167 B2 JP5297167 B2 JP 5297167B2
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- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title claims abstract description 25
- 125000000732 arylene group Chemical group 0.000 claims abstract description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 152
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 44
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 abstract description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 32
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 abstract description 18
- 239000010410 layer Substances 0.000 description 224
- 239000000126 substance Substances 0.000 description 109
- 150000003252 quinoxalines Chemical class 0.000 description 99
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 92
- 230000015572 biosynthetic process Effects 0.000 description 79
- 238000003786 synthesis reaction Methods 0.000 description 79
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 239000000463 material Substances 0.000 description 69
- 150000001875 compounds Chemical class 0.000 description 65
- -1 fluorene-diyl group Chemical group 0.000 description 63
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- 235000019441 ethanol Nutrition 0.000 description 45
- 229910052757 nitrogen Inorganic materials 0.000 description 45
- 239000010408 film Substances 0.000 description 44
- 238000000034 method Methods 0.000 description 44
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
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- 238000001704 evaporation Methods 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
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- 230000006870 function Effects 0.000 description 21
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
- 150000002894 organic compounds Chemical class 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 19
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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- 150000002367 halogens Chemical class 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
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- 239000000956 alloy Substances 0.000 description 17
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 150000005072 1,3,4-oxadiazoles Chemical class 0.000 description 14
- 238000000295 emission spectrum Methods 0.000 description 14
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- 239000011159 matrix material Substances 0.000 description 14
- 238000005259 measurement Methods 0.000 description 14
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 14
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 14
- 239000010409 thin film Substances 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 13
- 239000012298 atmosphere Substances 0.000 description 13
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- 150000001340 alkali metals Chemical class 0.000 description 12
- 150000001639 boron compounds Chemical class 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 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 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- 150000001342 alkaline earth metals Chemical class 0.000 description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 11
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound 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 11
- 238000004544 sputter deposition Methods 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [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
- 229910052782 aluminium Inorganic materials 0.000 description 10
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 10
- 239000011777 magnesium Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 10
- 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 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- 239000011630 iodine Substances 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 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 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 9
- 239000010453 quartz Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 239000000706 filtrate Substances 0.000 description 8
- 239000012212 insulator Substances 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 238000007740 vapor deposition Methods 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- OEORUYSCTDQZEX-UHFFFAOYSA-N 2-phenyl-5-[4-[4-(3-phenylquinoxalin-2-yl)phenyl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2C(=NC3=CC=CC=C3N=2)C=2C=CC=CC=2)O1 OEORUYSCTDQZEX-UHFFFAOYSA-N 0.000 description 7
- MQPRIOGKRYMSDI-UHFFFAOYSA-N 2-phenyl-5-[4-[4-[3-[4-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]phenyl]quinoxalin-2-yl]phenyl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2C(=NC3=CC=CC=C3N=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2OC(=NN=2)C=2C=CC=CC=2)O1 MQPRIOGKRYMSDI-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 229910010272 inorganic material Inorganic materials 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 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 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 229910052814 silicon oxide Inorganic materials 0.000 description 7
- 229910001930 tungsten oxide Inorganic materials 0.000 description 7
- UQVFZEYHQJJGPD-UHFFFAOYSA-N 9-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 UQVFZEYHQJJGPD-UHFFFAOYSA-N 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 238000010549 co-Evaporation Methods 0.000 description 6
- 230000005284 excitation Effects 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- 150000002484 inorganic compounds Chemical class 0.000 description 6
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- REKFALFAMJBFCR-UHFFFAOYSA-N 1-(4-bromophenyl)-2-phenylethane-1,2-dione Chemical compound C1=CC(Br)=CC=C1C(=O)C(=O)C1=CC=CC=C1 REKFALFAMJBFCR-UHFFFAOYSA-N 0.000 description 4
- XLHCHVUFUPJPEO-UHFFFAOYSA-N 1-bromo-4-(2-phenylethynyl)benzene Chemical group C1=CC(Br)=CC=C1C#CC1=CC=CC=C1 XLHCHVUFUPJPEO-UHFFFAOYSA-N 0.000 description 4
- WATVCMJLZPTSSS-UHFFFAOYSA-N 2,3-bis(4-bromophenyl)quinoxaline Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=C(Br)C=C1 WATVCMJLZPTSSS-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 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 4
- 150000001298 alcohols Chemical class 0.000 description 4
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Description
タイシ ツジ,他5名,SID 04 DIGEST,35,PP900−903(2004)
また、本発明のキノキサリン誘導体を発光素子に用いることにより、駆動電圧の低い発光素子を得ることができる。また、消費電力の小さい発光素子を得ることができる。
本実施の形態では、本発明のキノキサリン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で示したキノキサリン誘導体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。
本実施の形態では、本発明に係る発光素子の一態様として、実施の形態1で示したキノキサリン誘導体を発光層に用いた構成について説明する。
本実施の形態では、本発明に係る発光素子の一態様として、実施の形態1で示したキノキサリン誘導体を電子注入層に用いた構成について説明する。
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、実施の形態2〜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2〜実施の形態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。
4−ブロモベンゾイルヒドラジンの合成スキームを(B−1)に示す。
N’−ベンゾイル−4−ブロモベンゾヒドラジドの合成スキームを(B−2)に示す。
2−(4−ブロモフェニル)−5−フェニル−1,3,4−オキサジアゾールの合成スキームを(B−3)に示す。
(4−ブロモフェニル)フェニルアセチレンの合成スキームを(B−4)に示す。
1−(4−ブロモフェニル)−2−フェニルエタンジオンの合成スキームを(B−5)に示す。
2−(4−ブロモフェニル)−3−フェニルキノキサリンの合成スキームを(B−6)に示す。
4−(3−フェニルキノキサリン−2−イル)フェニルボロン酸の合成スキームを(B−7)に示す。
O111PQの合成スキームを(B−8)に示す。
2,3−ビス(4−ブロモフェニル)キノキサリンの合成スキームを(C−1)に示す。
4,4’−(キノキサリン−2,3−ジイル)ジフェニルボロン酸の合成スキームを(C−2)に示す。
O112PQの合成スキームを(C−3)に示す。
発光素子1と同一基板を用い、O111PQ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1と同様に作製した。つまり、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を30nmの膜厚となるように成膜し、電子輸送層2114を形成した。電子輸送層2114以外は発光素子1と同様に作製した。
発光素子3と同一基板を用い、O111PQ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と同様に作製した。つまり、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を10nmの膜厚となるように成膜し、電子輸送層(A)2214を形成した。電子輸送層(A)2214以外は発光素子3と同様に作製した。
発光素子5と同一基板を用い、O111PQ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5と同様に作製した。つまり、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を30nmの膜厚となるように成膜し、電子輸送層2114を形成した。電子輸送層2114以外は発光素子5と同様に作製した。
発光素子7と同一基板を用い、O111PQ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7と同様に作製した。つまり、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を10nmの膜厚となるように成膜し、電子輸送層(A)2214を形成した。電子輸送層(A)2214以外は発光素子7と同様に作製した。
102 第1の電極
103 EL層
104 第2の電極
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
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 正孔輸送層
2113 発光層
2114 電子輸送層
2115 電子注入層
2201 ガラス基板
2202 第1の電極
2204 第2の電極
2211 複合材料を含む層
2212 正孔輸送層
2213 発光層
2214 電子輸送層(A)
2215 電子輸送層(B)
2216 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 (13)
- 請求項1乃至請求項5のいずれか一項において、
R1は、フェニル基またはビフェニル基であることを特徴とするキノキサリン誘導体。 - 一対の電極間に、請求項1乃至請求項9のいずれか一項に記載のキノキサリン誘導体を有する発光素子。
- 陽極と陰極との間に、発光層と、請求項1乃至請求項9のいずれか一項に記載のキノキサリン誘導体を含む層を有し、
前記キノキサリン誘導体を含む層は、前記発光層と前記陰極との間に設けられていることを特徴とする発光素子。 - 請求項11または請求項12に記載の発光素子と、前記発光素子の発光を制御する制御回路とを有する発光装置。
- 表示部を有し、
前記表示部は、請求項11または請求項12のいずれか一項に記載の発光素子と前記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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JP2006151887A (ja) * | 2004-11-30 | 2006-06-15 | Semiconductor Energy Lab Co Ltd | 有機金属錯体およびそれを用いた発光素子、発光装置 |
JP4376859B2 (ja) * | 2004-12-03 | 2009-12-02 | 株式会社半導体エネルギー研究所 | 有機金属錯体 |
JP4312753B2 (ja) * | 2004-12-03 | 2009-08-12 | 株式会社半導体エネルギー研究所 | 有機金属錯体 |
WO2008047589A1 (en) | 2006-10-06 | 2008-04-24 | Semiconductor Energy Laboratory Co., Ltd. | Quinoxaline derivative, and light-emitting element and light-emitting device using quinoxaline derivative |
-
2008
- 2008-11-20 KR KR1020080115727A patent/KR101564762B1/ko active IP Right Grant
- 2008-11-25 US US12/277,433 patent/US7927720B2/en not_active Expired - Fee Related
- 2008-11-28 JP JP2008304456A patent/JP5297167B2/ja not_active Expired - Fee Related
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KR20090056840A (ko) | 2009-06-03 |
US7927720B2 (en) | 2011-04-19 |
JP2009149632A (ja) | 2009-07-09 |
KR101564762B1 (ko) | 2015-10-30 |
US20090140641A1 (en) | 2009-06-04 |
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