JP2012102091A - 有機金属錯体およびこれを用いた発光素子、表示装置 - Google Patents
有機金属錯体およびこれを用いた発光素子、表示装置 Download PDFInfo
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- JP2012102091A JP2012102091A JP2011226451A JP2011226451A JP2012102091A JP 2012102091 A JP2012102091 A JP 2012102091A JP 2011226451 A JP2011226451 A JP 2011226451A JP 2011226451 A JP2011226451 A JP 2011226451A JP 2012102091 A JP2012102091 A JP 2012102091A
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- carbon atoms
- alkyl group
- general formula
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- 125000002524 organometallic group Chemical group 0.000 title claims abstract description 163
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 115
- 229910052751 metal Inorganic materials 0.000 claims abstract description 93
- 239000002184 metal Substances 0.000 claims abstract description 93
- 239000003446 ligand Substances 0.000 claims abstract description 52
- 125000001424 substituent group Chemical group 0.000 claims abstract description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 277
- 125000000217 alkyl group Chemical group 0.000 claims description 192
- 239000001257 hydrogen Substances 0.000 claims description 106
- 229910052739 hydrogen Inorganic materials 0.000 claims description 106
- 125000003545 alkoxy group Chemical group 0.000 claims description 99
- 239000000126 substance Substances 0.000 claims description 80
- 125000005843 halogen group Chemical group 0.000 claims description 67
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
- 150000002431 hydrogen Chemical class 0.000 claims description 52
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 38
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 13
- 239000013522 chelant Substances 0.000 claims description 11
- 229910052741 iridium Inorganic materials 0.000 claims description 10
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 229910052697 platinum Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000005594 diketone group Chemical group 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims 1
- LNJZJDLDXQQJSG-UHFFFAOYSA-N 2-phenylpyrazine Chemical class C1=CC=CC=C1C1=CN=CC=N1 LNJZJDLDXQQJSG-UHFFFAOYSA-N 0.000 abstract description 10
- 239000010410 layer Substances 0.000 description 222
- 238000005401 electroluminescence Methods 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
- 150000001875 compounds Chemical class 0.000 description 39
- 239000000758 substrate Substances 0.000 description 38
- 239000000463 material Substances 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 31
- -1 halogenated pyrazine compound Chemical class 0.000 description 29
- 150000002894 organic compounds Chemical class 0.000 description 29
- 238000002347 injection Methods 0.000 description 28
- 239000007924 injection Substances 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000010408 film Substances 0.000 description 22
- 230000005525 hole transport Effects 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 230000005281 excited state Effects 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 238000000862 absorption spectrum Methods 0.000 description 18
- 239000011159 matrix material Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000000295 emission spectrum Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000007850 fluorescent dye Substances 0.000 description 14
- 238000005192 partition Methods 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- 239000002131 composite material Substances 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 239000010453 quartz Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000005284 excitation Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000011575 calcium Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 230000005283 ground state Effects 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 239000012212 insulator Substances 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 7
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 7
- 238000007789 sealing Methods 0.000 description 7
- 238000001308 synthesis method Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 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 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 6
- 239000000956 alloy Substances 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
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 150000004696 coordination complex Chemical class 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000002194 synthesizing effect Effects 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 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 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 229910052749 magnesium 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
- 229910021645 metal ion Inorganic materials 0.000 description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
- 239000000565 sealant Substances 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 229910052814 silicon oxide Inorganic materials 0.000 description 5
- 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 5
- 239000011701 zinc Substances 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
- 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 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- 229940093475 2-ethoxyethanol Drugs 0.000 description 4
- MKAQNAJLIITRHR-UHFFFAOYSA-N 3-(3-dibenzothiophen-4-ylphenyl)phenanthro[9,10-b]pyrazine Chemical compound C1=CC=C2C3=NC(C=4C=CC=C(C=4)C4=C5SC=6C(C5=CC=C4)=CC=CC=6)=CN=C3C3=CC=CC=C3C2=C1 MKAQNAJLIITRHR-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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 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
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 4
- 229910001947 lithium oxide Inorganic materials 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 229910001930 tungsten oxide Inorganic materials 0.000 description 4
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 3
- 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 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
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229910052769 Ytterbium Inorganic materials 0.000 description 3
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-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
- 125000005595 acetylacetonate group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 229910000423 chromium oxide Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 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 3
- 239000003921 oil Substances 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
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003216 pyrazines Chemical class 0.000 description 3
- 229910052761 rare earth metal Inorganic materials 0.000 description 3
- 150000002910 rare earth metals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 229910003449 rhenium oxide Inorganic materials 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229910001936 tantalum oxide Inorganic materials 0.000 description 3
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 229910001935 vanadium oxide Inorganic materials 0.000 description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 3
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 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
- ZRPRRAOCEABMND-UHFFFAOYSA-K trichloroiridium;hydrate;hydrochloride Chemical compound O.Cl.Cl[Ir](Cl)Cl ZRPRRAOCEABMND-UHFFFAOYSA-K 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
【解決手段】下記一般式(G0)で表されるフェニルピラジン誘導体が、第9族または第10族の金属イオンによりオルトメタル化されることにより形成された、下記一般式(G1)で表される構造を有し、下記一般式(G1)は下記一般式(G2)で表される置換基をフェニル基に少なくとも1つ以上有した有機金属錯体を提供する。また、前記有機金属錯体を含んで形成された発光素子、発光装置を提供する。
【選択図】なし
Description
本実施の形態では、本発明の一態様である有機金属錯体について説明をする。
下記一般式(G0)で表されるフェニルピラジン誘導体は、以下のような簡便な合成スキームにより合成できる。例えば、下記スキーム(a)に示すように、フェニルボロン酸(A1)とハロゲン化ピラジン化合物(A2)とをカップリングすることにより得られる。あるいは、下記スキーム(a’)に示すように、アリールのジケトン(A1’)とジアミン(A2’)を反応させることにより得られる。なお、下記一般式(G0)において、R1は炭素数1〜4のアルキル基、または炭素数1〜4のアルコキシ基、または炭素数1〜5のアルコキシカルボニル基のいずれかを表す。また、R2及びR3はそれぞれ独立に水素、または炭素数1〜4のアルキル基のいずれかを表す。また、R4、R5、R6及びR7は、それぞれ独立に水素、または炭素数1〜4のアルキル基、または炭素数1〜4のアルコキシ基、またはハロゲン基、またはトリフルオロメチル基、またはフェニル基のいずれかを表す。なお、アルキル基は、フェニル基で置換されていても良い。また、下記スキーム(a)中のXはハロゲン元素を表す。
次に、一般式(G1)で表される構造を有する有機金属錯体の好ましい具体例である、下記一般式(G6)で表される有機金属錯体の合成法について説明する。
次に、一般式(G1)で表される構造を有する有機金属錯体の好ましい具体例である、下記一般式(G10)で表される有機金属錯体の合成法について説明する。
本実施の形態では、本発明の一態様として、有機金属錯体を発光層に用いた発光素子について図1を用いて説明する。
本発明の一態様である発光素子は、複数の発光層を有するものであってもよい。複数の発光層を設け、それぞれの発光層から発光させることで、複数の発光が混合された発光を得ることができる。したがって、例えば白色光を得ることができる。本実施の形態では、複数の発光層を有する発光素子の態様について図2を用いて説明する。
本実施の形態では、本発明の一態様として、発光素子においてEL層を複数有する構造(以下、積層型素子という)について、図3を用いて説明する。この発光素子は、第1の電極301と第2の電極304との間に、複数のEL層(第1のEL層302、第2のEL層303)を有する積層型発光素子である。なお、本実施の形態では、EL層が2層の場合について示すが、3層以上としても良い。
本実施の形態では、本発明の一態様として、有機金属錯体を増感剤として用いた発光素子の態様について、図1を用いて説明する。
本実施の形態では、本発明の一態様として、発光素子を用いて作製される発光装置であるパッシブマトリクス型の発光装置、およびアクティブマトリクス型の発光装置について説明する。
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7、図8および図9を用いて説明する。
本実施の形態では、左目用の映像と右目用の映像を高速で切り換える表示装置を用いて、表示装置の映像と同期する専用の眼鏡を用いて動画または静止画である3D映像を視認する例を、図9を用いて示す。
本実施例では、実施の形態1の構造式(100)で表される本発明の一態様である有機金属錯体、(アセチルアセトナート)ビス[3,5−ジメチル−2−(4−フェノキシフェニル)ピラジナート]イリジウム(III)(略称:[Ir(dmpoppr)2(acac)])の合成例を具体的に例示する。なお、[Ir(dmpoppr)2(acac)]の構造を以下に示す。
まず、2−クロロ−3,5−ジメチルピラジン1.35gと4−フェノキシフェニルボロン酸2.02g、炭酸ナトリウム1.00g、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド(略称:Pd(PPh3)2Cl2)0.043g、水15mL、アセトニトリル15mLを、還流管を付けたナスフラスコに入れ、内部をアルゴン置換した。この反応容器にマイクロ波(2.45GHz,100W)を10分間照射することで加熱し、反応させた。その後、この反応溶液に水を加え、ジクロロメタンにて抽出した。得られた抽出液を水で洗浄し、硫酸マグネシウムにて乾燥した。乾燥した後の溶液を濾過した。この溶液の溶媒を留去した後、得られた残渣をメタノールで洗浄し、目的のピラジン誘導体Hdmpopprを得た(白色粉末、収率89%)。なお、マイクロ波の照射はマイクロ波合成装置(CEM社製,Discover)を用いた。ステップ1の合成スキームを下記(e)に示す。
次に、2−エトキシエタノール9mLと水3mL、上記ステップ1で得たHdmpoppr0.91g、塩化イリジウム水和物(IrCl3・H2O)0.45gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz、100W)を30分間照射し、反応させた。反応溶液より析出してきた粉末を濾過し、エタノールで洗浄することにより、複核錯体[Ir(dmpoppr)2Cl]2を得た(褐色粉末、収率80%)。ステップ2の合成スキームを下記(f)に示す。
さらに、2−エトキシエタノール10mL、上記ステップ2で得た複核錯体[Ir(dmpoppr)2Cl]20.94g、アセチルアセトン0.19mL、炭酸ナトリウム0.64gを、還流管を付けたナスフラスコに入れ、フラスコ内をアルゴン置換した。その後、マイクロ波(2.45GHz 100W)を30分間照射し、反応させた。反応溶液より析出してきた粉末を濾過し、エタノールで洗浄した後、ジクロロメタンに溶解した。この溶液を濾過することにより不溶物を除去し、濃縮した。得られた残渣を、ジクロロメタンとメタノールの混合溶媒にて再結晶することにより、本発明の有機金属錯体[Ir(dmpoppr)2(acac)]を得た(橙色粉末、収率56%)。ステップ3の合成スキームを下記(h)に示す。
本実施例では、実施の形態1の構造式(130)で表される本発明の一態様である有機金属錯体、トリス[3,5−ジメチル−2−(4−フェノキシフェニル)ピラジナート]イリジウム(III)(略称:[Ir(dmpoppr)3])の合成例を具体的に例示する。なお、[Ir(dmpoppr)3]の構造を以下に示す。
まず、上記合成例1のステップ1で得られた配位子Hdmpoppr1.42g、トリス(アセチルアセトナート)イリジウム(III)0.50g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43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、この溶液を濾過した。濾液の溶媒を留去し、得られた残渣を酢酸エチル、次いでメタノールにて洗浄した後、ジクロロメタンにて再結晶することにより、本発明の一態様である有機金属錯体[Ir(dmpoppr)3]を得た(橙色粉末、収率22%)。合成スキームを下記(f)に示す。
まず、ガラス製の基板1100上に第1の電極1101として110nmの膜厚で酸化珪素を含むインジウム錫酸化物(ITSO)を成膜する。なお、ITSO表面が、2mm角の大きさで露出するように周辺が絶縁膜で覆われている。ここで、第1の電極1101は、発光素子(発光素子1および発光素子2)の陽極として機能する電極である。
作製した発光素子(発光素子1および発光素子2)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。
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。
上記実施例で用いた、2−[3−(ジベンゾチオフェン−4−イル)フェニル]ジベンゾ[f,h]キノキサリン(略称:2mDBTPDBq−II)の合成方法について具体的に説明する。2mDBTPDBq−IIの構造を以下に示す。
2−[3−(ジベンゾチオフェン−4−イル)フェニル]ジベンゾ[f,h]キノキサリン(略称:2mDBTPDBq−II)の合成スキームを(y)に示す。
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
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 第1の発光層
214 分離層
215 第2の発光層
216 電子輸送層
217 電子注入層
301 第1の電極
302 第1のEL層
303 第2のEL層
304 第2の電極
305 電荷発生層
401 基板
402 絶縁層
403 第1の電極
404 第1の隔壁
405 発光領域
406 第2の隔壁
407 EL層
408 第2の電極
410 分離領域
501 基板
503 走査線
505 領域
506 第2の隔壁
508 データ線
509 接続配線
510 入力端子
511a FPC
511b FPC
512 入力端子
601 素子基板
602 画素部
603 駆動回路部(ソース側駆動回路)
604 駆動回路部(ゲート側駆動回路)
605 シール材
606 封止基板
607 引き回し配線
608 FPC(フレキシブルプリントサーキット)
609 nチャネル型TFT
610 pチャネル型TFT
611 スイッチング用TFT
612 電流制御用TFT
613 陽極
614 絶縁物
615 EL層
616 陰極
617 発光素子
618 空間
801 照明装置
802 照明装置
1100 基板
1101 第1の電極
1102 EL層
1103 第2の電極
1111 正孔注入層
1112 正孔輸送層
1113 発光層
1114 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
7200 コンピュータ
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
7300 携帯型遊技機
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
7500 卓上照明器具
7501 照明部
7502 傘
7503 可変アーム
7504 支柱
7505 台
7506 電源スイッチ
9100 3D映像表示装置
9101 表示部
9102 眼鏡本体
9103a 左目用パネル
9103b 右目用パネル
9104 ケーブル
9113 タイミング発生器
9116 表示制御回路
9117 表示部
9118 ソース線側駆動回路
9119 ゲート線側駆動回路
9122 外部操作手段
9130a 同期信号
9130b 同期信号
9131a 同期信号
9131b 同期信号
Claims (17)
- 一般式(G1)で表される構造を有する有機金属錯体。
- 一般式(G3)で表される構造を有する有機金属錯体。
- 一般式(G4)で表される構造を有する有機金属錯体。
- 一般式(G5)で表される構造を有する有機金属錯体。
- 一般式(G6)で表される有機金属錯体。
- 一般式(G7)で表される有機金属錯体。
- 一般式(G8)で表される有機金属錯体。
- 一般式(G9)で表される有機金属錯体。
- 請求項5乃至請求項8のいずれか一項において前記モノアニオン性の配位子が、ベータジケトン構造を有するモノアニオン性の二座キレート配位子、カルボキシル基を有するモノアニオン性の二座キレート配位子、フェノール性水酸基を有するモノアニオン性の二座キレート配位子、2つの配位元素がいずれも窒素であるモノアニオン性の二座キレート配位子のいずれかである有機金属錯体。
- 請求項5乃至請求項8のいずれか一項において、前記モノアニオン性の配位子は、構造式(L1)乃至(L6)のいずれかで表される配位子である有機金属錯体。
- 一般式(G10)で表される有機金属錯体。
- 一般式(G11)で表される有機金属錯体。
- 一般式(G12)で表される有機金属錯体。
- 一般式(G13)で表される有機金属錯体。
- 請求項1乃至請求項14のいずれか一項に記載の有機金属錯体において、前記中心金属Mが、イリジウムまたは白金である有機金属錯体。
- 請求項1乃至請求項15のいずれか一項に記載の有機金属錯体を、発光物質として含む発光素子。
- 請求項16に記載の発光素子を有する発光装置。
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Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2433929B1 (en) * | 2010-09-27 | 2013-10-23 | Semiconductor Energy Laboratory Co, Ltd. | Organic Compound, Light-Emitting Element, Light-Emitting Device, Electronic Device, and Lighting Device |
TWI523845B (zh) | 2011-12-23 | 2016-03-01 | 半導體能源研究所股份有限公司 | 有機金屬錯合物,發光元件,發光裝置,電子裝置及照明裝置 |
US9231217B2 (en) * | 2013-11-28 | 2016-01-05 | Semiconductor Energy Laboratory Co., Ltd. | Synthesis method of organometallic complex, synthesis method of pyrazine derivative, 5,6-diaryl-2-pyrazyl triflate, light-emitting element, light-emitting device, electronic device, and lighting device |
KR102088883B1 (ko) * | 2013-12-02 | 2020-03-16 | 엘지디스플레이 주식회사 | 유기전계발광표시장치 |
WO2015118426A2 (en) * | 2014-02-06 | 2015-08-13 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, lighting device, and electronic appliance |
WO2017082169A1 (ja) * | 2015-11-10 | 2017-05-18 | シャープ株式会社 | 発光素子およびその製造方法並びに発光方法 |
CN105418686A (zh) * | 2015-12-24 | 2016-03-23 | 北京北达聚邦科技有限公司 | 一种吡嗪磷光铱配合物及其制备方法和应用 |
US11910702B2 (en) * | 2017-11-07 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent devices |
KR20210082908A (ko) * | 2019-12-26 | 2021-07-06 | 엘지디스플레이 주식회사 | 전계 발광 표시 장치 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002175884A (ja) * | 2000-09-26 | 2002-06-21 | Canon Inc | 発光素子及び発光素子用金属配位化合物 |
WO2005097943A1 (ja) * | 2004-03-31 | 2005-10-20 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP2007161859A (ja) * | 2005-12-13 | 2007-06-28 | Showa Denko Kk | 高分子発光材料、有機エレクトロルミネッセンス素子および表示装置 |
JP2007182429A (ja) * | 2005-12-05 | 2007-07-19 | Semiconductor Energy Lab Co Ltd | 有機金属錯体および前記錯体を用いた発光素子、発光装置、並びに電子機器 |
JP2010189376A (ja) * | 2009-01-21 | 2010-09-02 | Semiconductor Energy Lab Co Ltd | 有機金属錯体およびこれを用いた発光素子、発光装置、電子機器並びに照明装置 |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4154139B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子 |
KR100825183B1 (ko) | 2000-11-30 | 2008-04-24 | 캐논 가부시끼가이샤 | 발광 소자 및 표시 장치 |
AU2002222565A1 (en) | 2000-11-30 | 2002-06-11 | Canon Kabushiki Kaisha | Luminescent element and display |
US6803720B2 (en) | 2000-12-15 | 2004-10-12 | Universal Display Corporation | Highly stable and efficient OLEDs with a phosphorescent-doped mixed layer architecture |
DE10238903A1 (de) | 2002-08-24 | 2004-03-04 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
DE10249926A1 (de) | 2002-10-26 | 2004-05-06 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
CN100488972C (zh) * | 2003-06-09 | 2009-05-20 | 日立化成工业株式会社 | 金属配位化合物、聚合物组合物、以及使用这些的有机电致发光元件 |
US7955716B2 (en) | 2003-06-09 | 2011-06-07 | Hitachi Chemical Co., Ltd. | Metal coordination compound, polymer composition, and organic electroluminescent device employing same |
JP4366332B2 (ja) | 2004-04-02 | 2009-11-18 | 株式会社半導体エネルギー研究所 | 有機金属錯体、該有機金属錯体を用いた発光素子および発光装置 |
US8084145B2 (en) | 2004-04-02 | 2011-12-27 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light emitting element using the complex, light emitting device using the element, and electric apparatus using the device |
JP4830283B2 (ja) | 2004-10-20 | 2011-12-07 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2006098460A1 (en) | 2005-03-17 | 2006-09-21 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, and light-emitting element, light-emitting device and electronic device using the organometallic complex |
JP4912704B2 (ja) | 2005-03-17 | 2012-04-11 | 株式会社半導体エネルギー研究所 | 有機金属錯体およびそれを用いた発光素子、発光装置、電子機器 |
CN101151270B (zh) | 2005-03-28 | 2011-04-06 | 株式会社半导体能源研究所 | 有机金属配合物,和使用它的发光装置和电子器件 |
US7960038B2 (en) | 2005-05-20 | 2011-06-14 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting device and electronic appliance using the same |
JP4906073B2 (ja) | 2005-05-20 | 2012-03-28 | 株式会社半導体エネルギー研究所 | 発光装置及びそれを用いた電子機器 |
WO2007066556A1 (en) | 2005-12-05 | 2007-06-14 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex and light-emitting element, light-emitting device and electronic device using the same |
TWI481616B (zh) | 2006-03-21 | 2015-04-21 | Semiconductor Energy Lab | 有機金屬錯合物及使用該有機金屬錯合物之發光元件,發光裝置和電子裝置 |
WO2008143113A1 (en) | 2007-05-18 | 2008-11-27 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, composition and light emitting element including the organometallic complex |
US20080312437A1 (en) | 2007-06-04 | 2008-12-18 | Semiconductor Energy Labratory Co., Ltd. | Organometallic Complex, and Light-Emitting Element, Light-Emitting Device, and Electronic Device Using the Organometallic Complex |
WO2008149828A1 (en) | 2007-06-05 | 2008-12-11 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, and light-emitting materia light-emitting element, light-emitting device and electronic device |
JP5271721B2 (ja) | 2008-01-23 | 2013-08-21 | 株式会社半導体エネルギー研究所 | トリアリールピラジン誘導体の製造方法 |
JP5530695B2 (ja) | 2008-10-23 | 2014-06-25 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、及び電子機器 |
US8399665B2 (en) | 2009-10-07 | 2013-03-19 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, and light-emitting element, light-emitting device, electronic device and electronic device using the organometallic complex |
JP5829828B2 (ja) | 2010-04-06 | 2015-12-09 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子及び発光装置 |
JP2012107003A (ja) | 2010-10-29 | 2012-06-07 | Semiconductor Energy Lab Co Ltd | 有機金属錯体およびこれを用いた発光素子、表示装置 |
-
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- 2016-11-02 US US15/341,380 patent/US9972794B2/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002175884A (ja) * | 2000-09-26 | 2002-06-21 | Canon Inc | 発光素子及び発光素子用金属配位化合物 |
WO2005097943A1 (ja) * | 2004-03-31 | 2005-10-20 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP2007182429A (ja) * | 2005-12-05 | 2007-07-19 | Semiconductor Energy Lab Co Ltd | 有機金属錯体および前記錯体を用いた発光素子、発光装置、並びに電子機器 |
JP2007161859A (ja) * | 2005-12-13 | 2007-06-28 | Showa Denko Kk | 高分子発光材料、有機エレクトロルミネッセンス素子および表示装置 |
JP2010189376A (ja) * | 2009-01-21 | 2010-09-02 | Semiconductor Energy Lab Co Ltd | 有機金属錯体およびこれを用いた発光素子、発光装置、電子機器並びに照明装置 |
Non-Patent Citations (2)
Title |
---|
JPN5013010745; GUIJIANG ZHOU: 'ROBUST TRIS-CYCLOMETALATED IRIDIUM(III) PHOSPHORS WITH LIGANDS 以下備考' CHEMISTRY - AN ASIAN JOURNAL V3 N10, 20081006, P1830-1841 * |
JPN6015020055; Zhou, Guijiang; Ho, Cheuk-Lam; Wong, Wai-Yeung; Wang, Qi; Ma, Dongge; Wang, Lixiang; Lin, Zhenyang;: 'Manipulating charge-transfer character with electron-withdrawing main-group moieties for the color t' Advanced Functional Materials 18(3), 2008, 499-511 * |
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US20140179920A1 (en) | 2014-06-26 |
US20120095226A1 (en) | 2012-04-19 |
JP2016027659A (ja) | 2016-02-18 |
JP6031168B2 (ja) | 2016-11-24 |
US8664383B2 (en) | 2014-03-04 |
US9490436B2 (en) | 2016-11-08 |
JP5812796B2 (ja) | 2015-11-17 |
CN102558236A (zh) | 2012-07-11 |
US9972794B2 (en) | 2018-05-15 |
US20170054093A1 (en) | 2017-02-23 |
CN102558236B (zh) | 2016-06-08 |
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