JP2014214127A - 燐光性有機金属イリジウム錯体の合成方法 - Google Patents
燐光性有機金属イリジウム錯体の合成方法 Download PDFInfo
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- JP2014214127A JP2014214127A JP2013093340A JP2013093340A JP2014214127A JP 2014214127 A JP2014214127 A JP 2014214127A JP 2013093340 A JP2013093340 A JP 2013093340A JP 2013093340 A JP2013093340 A JP 2013093340A JP 2014214127 A JP2014214127 A JP 2014214127A
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- light
- nitrogen
- iridium complex
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 53
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000001308 synthesis method Methods 0.000 title claims abstract description 17
- 229910052751 metal Inorganic materials 0.000 title abstract description 8
- 239000002184 metal Substances 0.000 title abstract description 8
- 230000008018 melting Effects 0.000 claims abstract description 5
- 238000002844 melting Methods 0.000 claims abstract description 5
- 230000004580 weight loss Effects 0.000 claims abstract description 4
- -1 nitrogen-containing heteroaromatic compound Chemical class 0.000 claims description 35
- 125000002524 organometallic group Chemical group 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- 238000005259 measurement Methods 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 150000002504 iridium compounds Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 33
- 230000015572 biosynthetic process Effects 0.000 abstract description 24
- 238000006243 chemical reaction Methods 0.000 abstract description 24
- 238000003786 synthesis reaction Methods 0.000 abstract description 24
- 239000002994 raw material Substances 0.000 abstract description 20
- 239000007983 Tris buffer Substances 0.000 abstract description 16
- 238000001465 metallisation Methods 0.000 abstract description 9
- 239000000243 solution Substances 0.000 abstract description 5
- 238000000354 decomposition reaction Methods 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 82
- 239000000126 substance Substances 0.000 description 34
- 239000007787 solid Substances 0.000 description 27
- 238000007122 ortho-metalation reaction Methods 0.000 description 24
- 238000002347 injection Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 150000002894 organic compounds Chemical class 0.000 description 8
- 239000004065 semiconductor Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 7
- 238000000859 sublimation Methods 0.000 description 7
- 230000008022 sublimation Effects 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VDHOGVHFPFGPIP-UHFFFAOYSA-N 9-[3-[5-(3-carbazol-9-ylphenyl)pyridin-3-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=NC=C(C=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 VDHOGVHFPFGPIP-UHFFFAOYSA-N 0.000 description 5
- 230000005281 excited state Effects 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- 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 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 4
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000013585 weight reducing agent Substances 0.000 description 4
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000002597 Solanum melongena Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 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
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 238000005092 sublimation method Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- AZFHXIBNMPIGOD-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;iridium Chemical compound [Ir].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O AZFHXIBNMPIGOD-LNTINUHCSA-N 0.000 description 2
- LWGTWWGANHDJRJ-UHFFFAOYSA-N 1-methyl-5-phenyl-3-propyl-1,2,4-triazole Chemical compound CN1N=C(CCC)N=C1C1=CC=CC=C1 LWGTWWGANHDJRJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 150000002390 heteroarenes Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 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 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
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- 238000004544 sputter deposition Methods 0.000 description 2
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- RTSZQXSYCGBHMO-UHFFFAOYSA-N 1,2,4-trichloro-3-prop-1-ynoxybenzene Chemical compound CC#COC1=C(Cl)C=CC(Cl)=C1Cl RTSZQXSYCGBHMO-UHFFFAOYSA-N 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- PZLZJGZGJHZQAU-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(CC)=CC=C1N1C(C=2C=CC(=CC=2)C(C)(C)C)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 PZLZJGZGJHZQAU-UHFFFAOYSA-N 0.000 description 1
- TVMBOHMLKCZFFW-UHFFFAOYSA-N 3-N,6-N,9-triphenyl-3-N,6-N-bis(9-phenylcarbazol-3-yl)carbazole-3,6-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC(=CC=C3N(C=3C=CC=CC=3)C2=CC=1)N(C=1C=CC=CC=1)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 TVMBOHMLKCZFFW-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- CUZCTQFIEMXSQG-UHFFFAOYSA-N 4-(2,6-dimethylphenyl)-3-(2-methylphenyl)-5-phenyl-1,2,4-triazole Chemical compound CC1=CC=CC=C1C(N1C=2C(=CC=CC=2C)C)=NN=C1C1=CC=CC=C1 CUZCTQFIEMXSQG-UHFFFAOYSA-N 0.000 description 1
- SMAJQIMJGFHCCR-UHFFFAOYSA-N 4-[3,5-di(dibenzothiophen-4-yl)phenyl]dibenzothiophene Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2C1=CC(C=2C=3SC4=CC=CC=C4C=3C=CC=2)=CC(C2=C3SC=4C(C3=CC=C2)=CC=CC=4)=C1 SMAJQIMJGFHCCR-UHFFFAOYSA-N 0.000 description 1
- LGDCSNDMFFFSHY-UHFFFAOYSA-N 4-butyl-n,n-diphenylaniline Polymers C1=CC(CCCC)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 LGDCSNDMFFFSHY-UHFFFAOYSA-N 0.000 description 1
- OKEZAUMKBWTTCR-AATRIKPKSA-N 5-methyl-2-[4-[(e)-2-[4-(5-methyl-1,3-benzoxazol-2-yl)phenyl]ethenyl]phenyl]-1,3-benzoxazole Chemical compound CC1=CC=C2OC(C3=CC=C(C=C3)/C=C/C3=CC=C(C=C3)C=3OC4=CC=C(C=C4N=3)C)=NC2=C1 OKEZAUMKBWTTCR-AATRIKPKSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- UFWDOFZYKRDHPB-UHFFFAOYSA-N 9-[3-[6-(3-carbazol-9-ylphenyl)pyridin-2-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(N=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 UFWDOFZYKRDHPB-UHFFFAOYSA-N 0.000 description 1
- LTUJKAYZIMMJEP-UHFFFAOYSA-N 9-[4-(4-carbazol-9-yl-2-methylphenyl)-3-methylphenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C(=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C)C(C)=C1 LTUJKAYZIMMJEP-UHFFFAOYSA-N 0.000 description 1
- XCICDYGIJBPNPC-UHFFFAOYSA-N 9-[4-[3,5-bis(4-carbazol-9-ylphenyl)phenyl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=C(C=C(C=2)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 XCICDYGIJBPNPC-UHFFFAOYSA-N 0.000 description 1
- 229910017073 AlLi Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
【解決手段】オルトメタル化の反応温度よりも融点が低く、オルトメタル化の反応温度(常圧下)における重量減少率が低く、また、オルトメタル化の際に分解しにくい分子量を有する含窒素複素芳香族化合物と、トリス(β−ジケトナート)イリジウムとをオルトメタル化させることにより燐光性有機金属イリジウム錯体を合成し、該オルトメタル化の際に未反応であった含窒素複素芳香族化合物を反応前と同じ構造のまま回収し、再度、トリス(β−ジケトナート)イリジウムとオルトメタル化させることにより、燐光性有機金属イリジウム錯体を合成する。
【選択図】図1
Description
本実施の形態では、本発明の一態様である燐光性有機金属イリジウム錯体の合成方法について、図1のフローチャートを基に説明する。
本実施の形態では、本発明の一態様である合成方法により得られた燐光性有機金属イリジウム錯体を発光層に用いた発光素子について図2を用いて説明する。
本実施例では、本発明の一態様である合成方法として、燐光性有機金属イリジウム錯体のトリス{2−[5−(2−メチルフェニル)−4−(2,6−ジメチルフェニル)−4H−1,2,4−トリアゾール−3−イル−κN2]フェニル−κC}イリジウム(III)を合成する方法について説明する。なお、本実施例の合成方法について、図3のフローチャートを基に説明する。また、[Ir(mpptz−dmp)3](略称)の構造を以下に示す。
3−フェニル−4−(2,6−ジメチルフェニル)−5−(2−メチルフェニル)−1,2,4−4H−トリアゾール(略称;Hmpptz−dmp)77.2g(227mmol)を3つのバッチ(バッチ1〜3)に分け、3つのバッチそれぞれを同様の条件で反応させた。一例としてバッチ1の合成例を示す。なお、ステップ1の合成スキームを下記(a−1)に示す。
原料である、Hmpptz−dmp(略称)40.0g(118mmol)および[Ir(acac)3](略称)11.6g(23.6mmol)を、三方コックを付けた200mLナスフラスコに入れ、270℃にて50時間加熱し、オルトメタル化(1回目)させた。得られた反応物Aにジクロロメタンを加えて超音波を照射し、吸引ろ過により固体Bを得た。ここでろ液のジクロロメタン溶液を液体Cとする。得られた固体Bはトルエンで再結晶し、目的物Dである[Ir(mpptz−dmp)3](略称)の黄色固体を9.0g、収率32%で得た。
次に、上記ステップ1で、ろ液として得た液体Cを、バッチ1〜3の3バッチからそれぞれ回収し、あわせて濃縮乾固した。得られた残渣を酢酸エチルで再結晶し、黄色固体62.9gを得た。なお、この黄色固体は、[Ir(acac)3](略称)と、Hmpptz−dmp(略称)を含む混合物(混合物E)であることを、Hmpptz−dmp(略称)の核磁気共鳴法(1H−NMR)による測定結果との比較により確認した。なお、Hmpptz−dmp(略称)を核磁気共鳴法(1H−NMR)により測定した1H−NMRチャートを図4、混合物Eを核磁気共鳴法(1H−NMR)により測定した1H−NMRチャートを図5にそれぞれ示す。図5の結果から、混合物Eに含まれるHmpptz−dmp(略称)と[Ir(acac)3](略称)のモル比は1:0.33であることがわかった。さらに、この1H−NMRチャートより回収したHmpptz−dmp(略称)に構造変化や分解が無いことがわかる。
次に、上記ステップ2で、ろ液として得た液体C’を回収し、濃縮乾固した。得られた残渣を酢酸エチルで再結晶し、黄色固体38.6gを得た。なお、この黄色固体は、[Ir(acac)3](略称)と、Hmpptz−dmp(略称)を含む混合物(混合物E’)であることを、図4に示したHmpptz−dmp(略称)の核磁気共鳴法(1H−NMR)による測定結果との比較により確認した。混合物E’を核磁気共鳴法(1H−NMR)により測定した1H−NMRチャートを図6に示す。図6の結果から、混合物E’に含まれるHmpptz−dmp(略称)と[Ir(acac)3](略称)のモル比は1:0.36であることがわかった。さらに、この1H−NMRチャートより回収したHmpptz−dmp(略称)に構造変化や分解が無いことがわかる。
1−メチル−5−フェニル−3−プロピル−1H−1,2,4−トリアゾール(略称:HnPrptz1−Me)0.50g、トリス(アセチルアセトナト)イリジウム(III)0.24gを、三方コックを付けた反応容器に入れ、反応容器内をアルゴン置換した。その後、250℃にて40時間加熱し、反応させた。反応物をジクロロメタンに溶解し、この溶液をろ過した。しかし、ろ取物は有機溶媒に不溶の褐色固体であり、目的物ではなかった。ろ液をシリカゲルカラムクロマトグラフィーにより分取し、目的物と配位子の回収を試みた。展開溶媒には、酢酸エチルを用いた。このろ液を分取したフラクションはそれぞれ、目的のイリジウム錯体、目的のイリジウム錯体と原料錯体であるトリス(アセチルアセトナト)イリジウム(III)の混合物、および分解したと考えられる配位子であり、元の原料である配位子HnPrptz1−Me(略称)は回収することが出来なかった。なお、ステップ1の合成スキームを(b−1)に示す。
まず、ガラス製の基板700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より成膜し、陽極として機能する第1の電極701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。
作製した発光素子1の動作特性について測定した。なお、測定は室温(25℃に保たれた雰囲気)で行った。
102 反応2
103 反応3
201 第1の電極
202 EL層
203 第2の電極
211 正孔注入層
212 正孔輸送層
213 発光層
214 電子輸送層
215 電子注入層
216 電荷発生層
700 基板
701 第1の電極
702 EL層
703 第2の電極
711 正孔注入層
712 正孔輸送層
713 発光層
714 電子輸送層
715 電子注入層
Claims (2)
- 融点が250℃以下で、かつ常圧下、250℃における示差熱−熱重量同時測定の重量減少率が5%以内であり、分子量が300以上700以下である含窒素複素芳香族化合物と、トリス(β−ジケトナート)イリジウムとをオルトメタル化させてオルトメタル化イリジウム化合物を合成した後、未反応の前記含窒素複素芳香族化合物を回収し、再度オルトメタル化させることを特徴とする燐光性有機金属イリジウム錯体の合成方法。
- 請求項1において、
前記含窒素複素芳香族化合物は、下記一般式(G0)で表されることを特徴とする燐光性有機金属イリジウム錯体の合成方法。
(但し、一般式(G0)中、Ph1〜Ph3は、それぞれ独立に置換もしくは無置換のフェニル基を表し、A1〜A3は、それぞれ独立に炭素または窒素を表す。なお、A1〜A3の全てが酸素、または全てが窒素の場合を除く。また、l、m、nは、それぞれ独立に0または1であり、その和は、2または3である。)
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CN106279113A (zh) * | 2015-06-26 | 2017-01-04 | 上海和辉光电有限公司 | 一种化合物及其制备方法和应用 |
US10923667B2 (en) | 2017-03-08 | 2021-02-16 | Samsung Electronics Co., Ltd. | Organometallic compound, composition containing the organometallic compound, and organic light-emitting device including the organometallic compound |
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JP2004168755A (ja) * | 2002-11-06 | 2004-06-17 | National Institute Of Advanced Industrial & Technology | オルトメタル化イリジウム錯体の製造方法 |
JP2012046479A (ja) * | 2009-11-02 | 2012-03-08 | Semiconductor Energy Lab Co Ltd | 有機金属錯体、発光素子、表示装置、電子機器、及び照明装置 |
JP2011190242A (ja) * | 2010-02-16 | 2011-09-29 | Semiconductor Energy Lab Co Ltd | 有機金属錯体及びそれを用いた発光素子、発光装置及び電子機器 |
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CN106279113A (zh) * | 2015-06-26 | 2017-01-04 | 上海和辉光电有限公司 | 一种化合物及其制备方法和应用 |
US10923667B2 (en) | 2017-03-08 | 2021-02-16 | Samsung Electronics Co., Ltd. | Organometallic compound, composition containing the organometallic compound, and organic light-emitting device including the organometallic compound |
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