JP2007519614A - 二座(Bipodal)配位子を有する金属錯体 - Google Patents
二座(Bipodal)配位子を有する金属錯体 Download PDFInfo
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- JP2007519614A JP2007519614A JP2006537137A JP2006537137A JP2007519614A JP 2007519614 A JP2007519614 A JP 2007519614A JP 2006537137 A JP2006537137 A JP 2006537137A JP 2006537137 A JP2006537137 A JP 2006537137A JP 2007519614 A JP2007519614 A JP 2007519614A
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- 239000003446 ligand Substances 0.000 title claims abstract description 54
- 150000004696 coordination complex Chemical class 0.000 title claims abstract 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 229910052751 metal Inorganic materials 0.000 claims description 36
- 239000002184 metal Substances 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000000412 dendrimer Substances 0.000 claims description 10
- 229920000736 dendritic polymer Polymers 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000013522 chelant Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 8
- -1 alkyl metal compound Chemical class 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 229910052790 beryllium Inorganic materials 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 230000005669 field effect Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- SSUONONIGQENDF-UHFFFAOYSA-N bis(6-phenylpyridin-2-yl)methanone Chemical compound C=1C=CC(C=2C=CC=CC=2)=NC=1C(=O)C(N=1)=CC=CC=1C1=CC=CC=C1 SSUONONIGQENDF-UHFFFAOYSA-N 0.000 claims description 3
- 229920000547 conjugated polymer Polymers 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- LEAJMTWVMWDZCK-UHFFFAOYSA-N 2,4-diphenylpyridine-3-carbonitrile Chemical compound N#CC1=C(C=2C=CC=CC=2)C=CN=C1C1=CC=CC=C1 LEAJMTWVMWDZCK-UHFFFAOYSA-N 0.000 claims description 2
- MZNQMFNJUQIOGH-UHFFFAOYSA-N 2-phenyl-6-[(6-phenylpyridin-2-yl)methyl]pyridine Chemical compound C=1C=CC(C=2C=CC=CC=2)=NC=1CC(N=1)=CC=CC=1C1=CC=CC=C1 MZNQMFNJUQIOGH-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 229910017255 AsSe Inorganic materials 0.000 claims description 2
- 229910017259 AsTe Inorganic materials 0.000 claims description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- 229910004013 NO 2 Inorganic materials 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 229910018321 SbTe Inorganic materials 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 150000005309 metal halides Chemical class 0.000 claims description 2
- 229910001960 metal nitrate Inorganic materials 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 2
- 229920001088 polycarbazole Polymers 0.000 claims description 2
- 229920002098 polyfluorene Polymers 0.000 claims description 2
- 229920001470 polyketone Polymers 0.000 claims description 2
- 229920000123 polythiophene Polymers 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052706 scandium Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- 229910052714 tellurium Inorganic materials 0.000 claims description 2
- 229910052716 thallium Inorganic materials 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000008204 material by function Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 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 4
- ZYSCNPHIRHCNNS-UHFFFAOYSA-N 2-[1-fluoro-1-(6-phenylpyridin-2-yl)ethyl]-6-phenylpyridine Chemical compound C=1C=CC(C=2C=CC=CC=2)=NC=1C(F)(C)C(N=1)=CC=CC=1C1=CC=CC=C1 ZYSCNPHIRHCNNS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- FAQKRQNOHLEVHR-UHFFFAOYSA-N bis(6-bromopyridin-2-yl)methanone Chemical compound BrC1=CC=CC(C(=O)C=2N=C(Br)C=CC=2)=N1 FAQKRQNOHLEVHR-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- VHPGVSAEXCWSHO-UHFFFAOYSA-N 1,1-bis(6-bromopyridin-2-yl)ethanol Chemical compound C=1C=CC(Br)=NC=1C(O)(C)C1=CC=CC(Br)=N1 VHPGVSAEXCWSHO-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012039 electrophile Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
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- 230000001681 protective effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
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- 230000007704 transition Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- VYBNUTHAXITORI-UHFFFAOYSA-N 2-bromo-6-[1-(6-bromopyridin-2-yl)-1-fluoroethyl]pyridine Chemical compound C=1C=CC(Br)=NC=1C(F)(C)C1=CC=CC(Br)=N1 VYBNUTHAXITORI-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
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- 150000000565 5-membered heterocyclic compounds Chemical class 0.000 description 1
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 239000003341 Bronsted base Substances 0.000 description 1
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- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
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- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 1
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
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- 125000002091 cationic group Chemical group 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
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- 230000008878 coupling Effects 0.000 description 1
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- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- 239000005457 ice water Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- Y02E10/549—Organic PV cells
Abstract
Description
1.寿命は、ほとんどの場合に、あまりにも短すぎ、これは、長寿命を有するOLEDの市場への導入の妨げとなっている。
2.効率は、しばしば、輝度の向上に伴い相当に低下することが、効率/輝度曲線から明らかである。このことは、実際には必要である非常に高い輝度は、高いパワー消費によってのみ得ることができるということを意味する。しかしながら、大きなパワー消費は、携帯用の装置(携帯電話、ラップトップ等)について高いバッテリーパワーを要求する。加えて、大部分が熱に変換される大きなパワー消費は、ディスプレイに熱的な損傷をもたらし得る。
一方で、例えば、電子輸送材料として用いられるAIQ3およびZnQ2のようなものは、水を付加する傾向を有する。
これらの、および同様のアルミニウムおよび亜鉛錯体の高い吸湿性は、重大な実用上の不利な点である。標準状態下で合成し貯蔵するAIQ3も、ヒドロキシキノリン配位子に加えて、錯体分子につき1モルの水を常に含有する(例えば、H.シュミットバウア(Schmidbaur)等、Z.Naturforsch., 1991, 46b, 901-911 を参照のこと)。この水は、除去することが非常に難しい。OLEDにおける使用のために、AIQ3およびZnQ2は、従って、複雑な、多工程の昇華プロセスにおける複雑な精製に供されなければならず、続いて、水を排除しながら保護ガス雰囲気下で貯蔵し取り扱わなければならない。さらに、個々のAIQ3のバッチの品質の大きなばらつき、および乏しい貯蔵安定性が、観察されている(S.カルク(Karg)、E−MRSコンファレンス、2000、ストラスブール)。
Si(OR1)2、−(CR2)R2Si(CR2)−、−(CR2CR2)R2Si(CR2CR2)−、−(SiR2)R2Si(SiR2)−、−(SiR2CR2)R2Si(CR2SiR2)−、−(CR2SiR2)R2Si(SiR2CR2)−、−(SiR2SiR2)R2Si(SiR2SiR2)−、R1N、−(CR2)R1N(CR2)−、−(CR2CR2)R1N(CR2CR2)−、FP、FPO、R1P、R1As、R1Sb、R1Bi、R1PO、R1AsO、R1SbO、R1BiO、R1PSe、R1AsSe、R1SbSe、R1BiSe、R1PTe、R1AsTe、R1SbTe、R1BiTe、−O−R1PO−O−、−O−(R1O)PO−O−、−CR2O−R1PO−OCR2−、−OCR2−R1PO−CR2O−、O、S、Se、−(CR2)O(CR2)−,−(CR2)S(CR2)−,−(CR2)(O)S(CR2)−、または−(CR2)(O)2S(CR2)−、または対応する非対称類似体であり、
Rは、出現毎に同一であるか異なり、H、F、Cl、Br、I、NO2、CN、1〜20のC原子を有する直鎖の、分岐の、若しくは環状のアルキル基若しくはアルコキシ基(ここで、1以上の非隣接のCH2基は、−R1C=CR1−、−C≡C−、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、−O−、−S−、−NR1−、または−CONR1−により置き換えられてもよく、また、1以上のH原子は、Fにより置き換えられてもよい)、または1〜14のC原子を有するアリール基、アリールオキシ基、若しくはヘテロアリール基(これは、1以上の非芳香族のR基により置換されていてもよい)であり、ここで、複数の置換基Rは、さらなる単環または多環式の脂肪族または芳香族環構造を示してもよく、および
R1、R2は、出現毎に同一であるか異なり、Hまたは1〜20のC原子を有する脂肪族若しくは芳香族炭化水素基である
架橋単位Vが、特に好ましい。
Mは、Be、Mg、Ca、Sr、Ba、Al、Ga、In、Tl、Sc、Y、La、Cr、Mo、W、Fe、Ru、Os、Co、Rh、Ir、Ni、Pd、Pt、Cu、Ag、Au、Zn、CdまたはHgであり、
Lは、出現毎に同一であるか異なり、C、N、またはPであり、
Qは、出現毎に同一であるか異なり、N、O、S、Se、またはTeであり、
Tは、出現毎に同一であるか異なり、NまたはPであり、
Xは、出現毎に同一であるか異なり、CR、N、またはPであり、
Yは、出現毎に同一であるか異なり、NR1、O、S、Se、Te、SO、SeO、TeO、SO2、SeO2、またはTeO2であり、
Zは、Vについて上記したものと同じ意味を有し、
cは、出現毎に同一であるか異なり、0または1である)。
他に示さない限り、以下の合成は、保護ガス雰囲気下、乾燥溶媒中で行った。出発材料を、アルドリッチまたはABCR[メチルマグネシウムクロライド(THF中3M)、ジエチルアミノサルファ三フッ化物(DAST)、ベンゼンボロン酸、(吹き付け乾燥させた)フッ化カリウム、トリ−tert−ブチルホスフィン、酢酸パラジウム(II)、テトラクロロ白金酸カリウム]から購入した。ジ(6−ブロモ−2−ピリジル)ケトンを、WO 98/22148 に記載される通りに調製した。シス−ジメチル−ジ(η1−S−ジメチルスルホキシジル)白金(II)を、エアボルン(Eaborn)等、J. Chem. Soc., Dalton Trans., 1981, 933-938 により記載される通りに調製した。
、94.0%の収率に対応する1.544g(2.8mmol)の生成物を与えた。
Claims (27)
- 構造2の四座キレート配位子Ligに配位した金属Metを含有することを特徴とする構造1の化合物。
- 電気的に中性であることを特徴とする請求項1に記載の化合物。
- L1=L2であることを特徴とする請求項1および/または2に記載の化合物。
- 前記架橋単位Vが、1〜6の原子を含有するか、または3員〜6員の同素環若しくは複素環であることを特徴とする請求項1〜3の一項以上に記載の化合物。
- 以下、すなわち、
Vは、BR1、−(CR2)R1B(CR2)−、−O−R1B−O−、−O−(R1O)B−O−、−CR2O−R1B−OCR2−、−(CR2CR2)R1B(CR2CR2)−、C=O、C=NR1、C=S、CR2、CR(OH)、CR(OR1)、C(NR1)2、−(CR2)R2C(CR2)−、−(CR2CR2)R2C(CR2CR2)−、−(SiR2)R2C(SiR2)−、−(SiR2CR2)R2C(CR2SiR2)−、−(CR2SiR2)R2C(SiR2CR2)−、−(SiR2SiR2)R2C(SiR2SiR2)−,シス−RC=CR、1,2−C6H4、1,3−C6H4、SiR2、Si(OH)2、
Si(OR1)2、−(CR2)R2Si(CR2)−、−(CR2CR2)R2Si(CR2CR2)−、−(SiR2)R2Si(SiR2)−、−(SiR2CR2)R2Si(CR2SiR2)−、−(CR2SiR2)R2Si(SiR2CR2)−、−(SiR2SiR2)R2Si(SiR2SiR2)−、R1N、−(CR2)R1N(CR2)−、−(CR2CR2)R1N(CR2CR2)−、FP、FPO、R1P、R1As、R1Sb、R1Bi、R1PO、R1AsO、R1SbO、R1BiO、R1PSe、R1AsSe、R1SbSe、R1BiSe、R1PTe、R1AsTe、R1SbTe、R1BiTe、−O−R1PO−O−、−O−(R1O)PO−O−、−CR2O−R1PO−OCR2−、−OCR2−R1PO−CR2O−、O、S、Se、−(CR2)O(CR2)−、−(CR2)S(CR2)−、−(CR2)(O)S(CR2)−、または−(CR2)(O)2S(CR2)−、または対応する非対称類似体であり、
Rは、出現毎に同一であるか異なり、H、F、Cl、Br、I、NO2、CN、1〜20のC原子を有する直鎖の、分岐の、若しくは環状のアルキル基若しくはアルコキシ基(ここで、1以上の非隣接のCH2基は、−R1C=CR1−、−C≡C−、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、−O−、−S−、−NR1−、または−CONR1−により置き換えられてもよく、また、1以上のH原子は、Fにより置き換えられてもよい)、または1〜14のC原子を有するアリール基、アリールオキシ基、若しくはヘテロアリール基(これは、1以上の非芳香族のR基により置換されていてもよい)であり、ここで、複数の置換基Rは、さらなる単環または多環式の脂肪族または芳香族環構造を示してもよく、および
R1、R2は、出現毎に同一であるか異なり、Hまたは1〜20のC原子を有する脂肪族若しくは芳香族炭化水素基であること
が、前記架橋部位Vに適用されることを特徴とする請求項1〜4の一項以上に記載の化合物。 - 化合物(1)〜(8)から選択され、このそれぞれが、1または2つのさらなる配位子L3を有し得る請求項1〜5の一項以上に記載の金属錯体。
Mは、Be、Mg、Ca、Sr、Ba、Al、Ga、In、Tl、Sc、Y、La、Cr、Mo、W、Fe、Ru、Os、Co、Rh、Ir、Ni、Pd、Pt、Cu、Ag、Au、Zn、CdまたはHgであり、
Lは、出現毎に同一であるか異なり、C、N、またはPであり、
Qは、出現毎に同一であるか異なり、N、O、S、Se、またはTeであり、
Tは、出現毎に同一であるか異なり、NまたはPであり、
Xは、出現毎に同一であるか異なり、CR、N、またはPであり、
Yは、出現毎に同一であるか異なり、NR1、O、S、Se、Te、SO、SeO、TeO、SO2、SeO2、またはTeO2であり、
Zは、請求項5においてVについて上記したものと同じ意味を有し、
cは、出現毎に同一であるか異なり、0または1である) - 存在する場合に、前記配位子L3は、二座キレート配位子であることを特徴とする請求項1〜8の一項以上に記載の金属錯体。
- 記号M=Be、Mg、PtまたはZnであり、添え字a=0であることを特徴とする請求項1〜10の一項以上に記載の化合物。
- 記号c=0およびM=Ptであることを特徴とする請求項11に記載の化合物。
- 記号M=RhまたはIrであり、および二座モノアニオン性配位子L3の場合には添え字a=1であり、単座モノアニオン性配位子L3の場合にはa=2であることを特徴とする請求項1〜10の一項以上に記載の化合物。
- 記号L=CまたはNであることを特徴とする請求項1〜13の一項以上に記載の化合物。
- 記号Q=OまたはSであることを特徴とする請求項1〜14の一項以上に記載の化合物。
- 記号T=Nであることを特徴とする請求項1〜15の一項以上に記載の化合物。
- 記号X=CRまたはNであることを特徴とする請求項1〜16の一項以上に記載の化合物。
- 記号Z=BR1、CR2、CO,SiR1 2、R1N、FP、FPO、R1P、R1PO、−CR2CR2−、−CR2−O−CR2−、−O−(OR1)PO−O−、シス−CR=CR、−CR2−BR1−CR2−、−CR2−CO−CR2−、−CR2−CR2−CR2−、または−CR2−NR1−CR2であることを特徴とする請求項1〜17の一項以上に記載の化合物。
- 記号R=H、F、Cl、Br、I、CN、1〜6のC原子を有する直鎖の、分岐の、環状のアルキル基若しくはアルコキシ基、または3〜10のC原子を有するアリール基若しくはヘテロアリール基(これは、1以上の非芳香族基Rにより置換されていてもよい)(ここで、同一の環状および2つの異なる環状の複数の置換基Rは、互いにさらなる単環または多環式の脂肪族環構造または芳香族環構造を形成してもよい)であることを特徴とする請求項1〜18の一項以上に記載の化合物。
- 請求項20に記載の前記化合物(31)〜(60)と、金属アルコキシドである化合物(61)、金属ケトケトナートである化合物(62)、金属ハライド、金属カルボン酸塩、金属硝酸塩および金属硫酸塩である化合物(63)、またはアルキル金属化合物若しくはアリール金属化合物である化合物(64)との反応による請求項1〜19の一項以上に記載の前記化合物の調製のための方法。
- 純度(1H−NMRおよび/またはHPLCにより決定)が、99%を超えることを特徴とする請求項1〜10の一項以上に記載の化合物。
- 構造1の化合物の1以上、または請求項1〜19の一項以上による化合物(1)〜(30)の1以上を含有する共役、部分共役および/または非共役ポリマーまたはデンドリマー。
- 請求項5において定義したR基の少なくとも1つが、前記ポリマーまたはデンドリマーへの結合を示すことを特徴とする請求項23に記載のポリマーまたはデンドリマー。
- 前記ポリマーが、ポリフルオレン、ポリスピロビフルオレン、ポリ−パラ−フェニレン、ポリジヒドロフェナントレン、ポリインデノフルオレン、ポリカルバゾール、ポリチオフェン、ポリケトン、ポリビニルカルバゾールの群から選択されるか、または上記した単位の複数を有するコポリマーから選択されることを特徴とする請求項23および/または24に記載のポリマー。
- 請求項1〜19および22〜25の一項以上に記載の化合物、ポリマー、コポリマーまたはデンドリマーの少なくとも1つを含む電子デバイス。
- 有機発光ダイオード(OLED)、有機集積回路(O−IC)、有機電界効果トランジスタ(OFET)、有機薄膜トランジスタ(OTFT)、有機太陽電池(O−SC)または有機レーザーダイオード(O−laser)であることを特徴とする請求項26に記載の電子デバイス。
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JP5230940B2 (ja) | 2013-07-10 |
US9029539B2 (en) | 2015-05-12 |
KR20060111456A (ko) | 2006-10-27 |
WO2005042550A1 (de) | 2005-05-12 |
EP1678190B1 (de) | 2012-11-21 |
EP1678190A1 (de) | 2006-07-12 |
DE10350722A1 (de) | 2005-05-25 |
CN1894269A (zh) | 2007-01-10 |
KR101135910B1 (ko) | 2012-04-16 |
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