JP5815280B2 - トリアゾール誘導体 - Google Patents
トリアゾール誘導体 Download PDFInfo
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- JP5815280B2 JP5815280B2 JP2011110966A JP2011110966A JP5815280B2 JP 5815280 B2 JP5815280 B2 JP 5815280B2 JP 2011110966 A JP2011110966 A JP 2011110966A JP 2011110966 A JP2011110966 A JP 2011110966A JP 5815280 B2 JP5815280 B2 JP 5815280B2
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- 150000003852 triazoles Chemical class 0.000 title claims description 82
- -1 dibenzothiophen-4-yl group Chemical group 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [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 group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 224
- 239000000126 substance Substances 0.000 description 72
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 239000000463 material Substances 0.000 description 61
- 150000001875 compounds Chemical class 0.000 description 55
- 239000000758 substrate Substances 0.000 description 48
- 238000000034 method Methods 0.000 description 40
- 230000005284 excitation Effects 0.000 description 36
- 238000002347 injection Methods 0.000 description 35
- 239000007924 injection Substances 0.000 description 35
- 239000010408 film Substances 0.000 description 34
- 150000002894 organic compounds Chemical class 0.000 description 33
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 30
- 238000005401 electroluminescence Methods 0.000 description 27
- 230000005525 hole transport Effects 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000012046 mixed solvent Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- 230000005281 excited state Effects 0.000 description 16
- 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
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 14
- 238000000862 absorption spectrum Methods 0.000 description 14
- 239000011159 matrix material Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- 229910052782 aluminium Inorganic materials 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 239000002131 composite material Substances 0.000 description 11
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 11
- 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 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 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 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 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 8
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 239000010453 quartz Substances 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 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 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
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 7
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 7
- 125000005595 acetylacetonate group Chemical group 0.000 description 7
- 229910045601 alloy Inorganic materials 0.000 description 7
- 239000000956 alloy Substances 0.000 description 7
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 7
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 7
- 239000007850 fluorescent dye Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000012212 insulator Substances 0.000 description 7
- 239000002346 layers by function Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000004544 sputter deposition Methods 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000000295 emission spectrum Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- 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 6
- 239000011701 zinc Substances 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910003437 indium oxide Inorganic materials 0.000 description 5
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 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 5
- 238000005192 partition Methods 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000010791 quenching Methods 0.000 description 5
- 230000000171 quenching effect Effects 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229910001930 tungsten oxide Inorganic materials 0.000 description 5
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 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 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 4
- 238000010549 co-Evaporation Methods 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 150000004826 dibenzofurans Chemical class 0.000 description 4
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000000737 periodic effect Effects 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 239000000565 sealant Substances 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
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 4
- 239000008096 xylene Substances 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 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 3
- MZWDAEVXPZRJTQ-WUXMJOGZSA-N 4-[(e)-(4-fluorophenyl)methylideneamino]-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1\N=C\C1=CC=C(F)C=C1 MZWDAEVXPZRJTQ-WUXMJOGZSA-N 0.000 description 3
- AEJARLYXNFRVLK-UHFFFAOYSA-N 4H-1,2,3-triazole Chemical class C1C=NN=N1 AEJARLYXNFRVLK-UHFFFAOYSA-N 0.000 description 3
- OOKRYIPMHLUQHU-UHFFFAOYSA-N 9-(4-bromophenyl)-9-phenylfluorene Chemical compound C1=CC(Br)=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 OOKRYIPMHLUQHU-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
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- 229910052769 Ytterbium Inorganic materials 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 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 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 150000001639 boron compounds Chemical class 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 229910000423 chromium oxide Inorganic materials 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229920000736 dendritic polymer Polymers 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 3
- 229910001947 lithium oxide Inorganic materials 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 3
- 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 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920002620 polyvinyl fluoride Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910003449 rhenium oxide Inorganic materials 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910001936 tantalum oxide Inorganic materials 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 229910001935 vanadium oxide Inorganic materials 0.000 description 3
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- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Description
本実施の形態では、本発明の一態様のトリアゾール誘導体について説明する。
はじめに合成スキーム(A−1)を以下に示す。
はじめに合成スキーム(B−1)を以下に示す。
本実施の形態では、本発明の一態様のトリアゾール誘導体をEL層に用いた発光素子について図1を用いて説明する。
本実施の形態は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発光素子である。
本実施の形態では、本発明の一態様の、発光素子を有する発光装置について図3を用いて説明する。なお、図3(A)は、発光装置を示す上面図、図3(B)は図3(A)をA−B及びC−Dで切断した断面図である。
本実施の形態では、本発明を適用した一態様である発光装置を用いて完成させた様々な電子機器および照明器具の一例について、図5、図6を用いて説明する。
本実施例では、上記構造式100に示した、3−[4−(ジベンゾチオフェン−4−イル)フェニル)]−4,5−ジフェニル−4H−1,2,4−トリアゾール(略称:DBTTAZ−II)の合成方法について説明する。
1H NMR(DMSO−d6、300MHz):δ(ppm)=7.34−7.45(m、5H)、7.52−7.66(m、11H)、7.76(d、J=8.4Hz、2H)、8.02−8.04(m、1H)、8.41−8.43(m、2H)。
まず、ガラス基板1100上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極1101を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
比較発光素子2の第1の発光層1113aは、9−[4−(4,5−ジフェニル−4H−1,2,4−トリアゾール−3−イル)フェニル]−9H−カルバゾール(略称:CzTAZ−I)、PCBA1BP、及びIr(ppy)3を共蒸着することで形成した。ここで、CzTAZ−I、PCBA1BP、及びIr(ppy)3の重量比は、1:0.25:0.08(=CzTAZ−I:PCBA1BP:Ir(ppy)3)となるように調節した。また、第1の発光層1113aの膜厚は20nmとした。
まず、ガラス基板1100上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極1101を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
本実施例では、上記構造式(150)に示した、4−[4−(ジベンゾチオフェン−4−イル)フェニル)]−3,5−ジフェニル−4H−1,2,4−トリアゾール(略称:4DBTTAZ−II)の合成方法について説明する。
1H NMR(CDCl3、300MHz):δ(ppm)=7.29(d、J=8.4Hz、2H)、7.33−7.44(m、6H)、7.49−7.53(m、7H)、7.59(t、J=7.8Hz、1H)、7.80(d、J=8.7Hz、2H)、7.85−7.88(m、1H)、8.20−8.22(m、2H)。
上記実施例で用いた4−フェニル−4’−(9−フェニルフルオレン−9−イル)トリフェニルアミン(略称:BPAFLP)の合成方法について具体的に説明する。BPAFLPの構造を以下に示す。
100mL三口フラスコにて、マグネシウムを1.2g(50mmol)減圧下で30分加熱撹拌し、マグネシウムを活性化させた。これを室温に冷まして窒素雰囲気にした後、ジブロモエタン数滴を加えて発泡、発熱するのを確認した。ここにジエチルエーテル10mL中に溶かした2−ブロモビフェニル12g(50mmol)をゆっくり滴下した後、2.5時間加熱還流撹拌してグリニヤール試薬とした。
100mL三口フラスコへ、9−(4−ブロモフェニル)−9−フェニルフルオレンを3.2g(8.0mmol)、4−フェニル−ジフェニルアミンを2.0g(8.0mmol)、ナトリウム tert−ブトキシドを1.0g(10mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)を23mg(0.04mmol)加え、フラスコ内の雰囲気を窒素置換した。この混合物へ、脱水キシレン20mLを加えた。この混合物を、減圧下で攪拌しながら脱気した後、トリ(tert−ブチル)ホスフィン(10wt%ヘキサン溶液)0.2mL(0.1mmol)を加えた。この混合物を、窒素雰囲気下、110℃で2時間加熱撹拌し、反応させた。
101 第1の電極
102 EL層
103 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
301 第1の電極
303 第2の電極
311 第1の発光ユニット
312 第2の発光ユニット
313 電荷発生層
401 ソース側駆動回路
402 画素部
403 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
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 発光層
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 基板
502 第1の電極
503 第2の電極
504 EL層
505 絶縁層
506 隔壁層
801 照明装置
802 照明装置
803 卓上照明器具
1100 基板
1101 第1の電極
1103 第2の電極
1111 正孔注入層
1112 正孔輸送層
1113 発光層
1113a 第1の発光層
1113b 第2の発光層
1114a 第1の電子輸送層
1114b 第2の電子輸送層
1115 電子注入層
7100 テレビジョン装置
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 ポインティングデバイス
7301 筐体
7302 筐体
7303 連結部
7304 表示部
7305 表示部
7306 スピーカ部
7307 記録媒体挿入部
7308 LEDランプ
7309 操作キー
7310 接続端子
7311 センサ
7312 マイクロフォン
7400 携帯電話機
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
7501 照明部
7502 傘
7503 可変アーム
7504 支柱
7505 台
7506 電源
Claims (6)
- 式(G1)で表されるトリアゾール誘導体のAr1〜Ar3のいずれか一に、式(G2)で表されるジベンゾチオフェン−4−イル基又はジベンゾフラン−4−イル基が結合したトリアゾール誘導体。
(式中、Aは、酸素又は硫黄を表し、Ar1〜Ar3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〜R7は、それぞれ独立に、水素、炭素数1〜4のアルキル基、又は置換もしくは無置換の炭素数6〜13のアリール基を表す。) - 請求項1において、
式(G2)で表されるジベンゾチオフェン−4−イル基が結合したAr 1 〜Ar 3 のいずれか一は、置換または無置換の炭素数6〜13のアリーレン基であるトリアゾール誘導体。 - 請求項1または請求項2において、
Ar 1 〜Ar 3 のうち、式(G2)で表されるジベンゾチオフェン−4−イル基が結合したいずれか一以外は、それぞれ、置換または無置換の炭素数6〜13のアリール基であるトリアゾール誘導体。 - 請求項1乃至請求項3のいずれか一において、
式(G2)で表されるジベンゾチオフェン−4−イル基が結合したAr 1 〜Ar 3 のいずれか一は、置換または無置換のフェニレン基であるトリアゾール誘導体。 - 請求項1乃至請求項4のいずれか一において、
Ar 1 〜Ar 3 のうち、式(G2)で表されるジベンゾチオフェン−4−イル基が結合したいずれか一以外は、それぞれ、置換または無置換のフェニル基であるトリアゾール誘導体。 - 式(100)、または式(150)で表されるトリアゾール誘導体。
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US8993125B2 (en) | 2015-03-31 |
US20160285005A1 (en) | 2016-09-29 |
TW201200509A (en) | 2012-01-01 |
TWI492944B (zh) | 2015-07-21 |
JP2016036033A (ja) | 2016-03-17 |
KR101889284B1 (ko) | 2018-08-20 |
KR20110128249A (ko) | 2011-11-29 |
JP6026613B2 (ja) | 2016-11-16 |
US9359335B2 (en) | 2016-06-07 |
JP2012006912A (ja) | 2012-01-12 |
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US20150197508A1 (en) | 2015-07-16 |
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