JP5198857B2 - 金属錯体 - Google Patents
金属錯体 Download PDFInfo
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- JP5198857B2 JP5198857B2 JP2007520763A JP2007520763A JP5198857B2 JP 5198857 B2 JP5198857 B2 JP 5198857B2 JP 2007520763 A JP2007520763 A JP 2007520763A JP 2007520763 A JP2007520763 A JP 2007520763A JP 5198857 B2 JP5198857 B2 JP 5198857B2
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- 150000004696 coordination complex Chemical class 0.000 title claims description 11
- 229910052751 metal Inorganic materials 0.000 claims abstract description 40
- 239000002184 metal Substances 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000003446 ligand Substances 0.000 claims description 67
- -1 aliphatic cyclic amine Chemical class 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims description 16
- 229910052741 iridium Inorganic materials 0.000 claims description 14
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 230000007935 neutral effect Effects 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 239000002739 cryptand Substances 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 125000004986 diarylamino group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910004013 NO 2 Inorganic materials 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 150000004294 cyclic thioethers Chemical class 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003949 imides Chemical class 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
- 150000002825 nitriles Chemical class 0.000 claims description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical class S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003375 sulfoxide group Chemical group 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- 150000007944 thiolates Chemical class 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 150000003577 thiophenes Chemical class 0.000 claims description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims 2
- 238000007142 ring opening reaction Methods 0.000 claims 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 1
- 235000008206 alpha-amino acids Nutrition 0.000 claims 1
- 238000010668 complexation reaction Methods 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 1
- 229940031826 phenolate Drugs 0.000 claims 1
- ANIDRZQDJXBHHM-UHFFFAOYSA-N pyridin-2-ylphosphane Chemical compound PC1=CC=CC=N1 ANIDRZQDJXBHHM-UHFFFAOYSA-N 0.000 claims 1
- 239000008204 material by function Substances 0.000 abstract description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229910021645 metal ion Inorganic materials 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 239000000412 dendrimer Substances 0.000 description 4
- 229920000736 dendritic polymer Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- OVGCSWSXJWSZDB-UHFFFAOYSA-N 1,3-bis(3-pyridin-2-ylphenyl)propan-2-ol Chemical compound C=1C=CC(C=2N=CC=CC=2)=CC=1CC(O)CC(C=1)=CC=CC=1C1=CC=CC=N1 OVGCSWSXJWSZDB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- QTZQLMLPWBTZOY-UHFFFAOYSA-N 1,3-bis(3-bromophenyl)propan-2-ol Chemical compound C=1C=CC(Br)=CC=1CC(O)CC1=CC=CC(Br)=C1 QTZQLMLPWBTZOY-UHFFFAOYSA-N 0.000 description 2
- SDLYCFCBTGWOCV-UHFFFAOYSA-N 1,3-bis(3-bromophenyl)propan-2-one Chemical compound BrC1=CC=CC(CC(=O)CC=2C=C(Br)C=CC=2)=C1 SDLYCFCBTGWOCV-UHFFFAOYSA-N 0.000 description 2
- ZLKMOIHCHCMSFW-UHFFFAOYSA-N 6-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(Cl)=N1 ZLKMOIHCHCMSFW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 229910001428 transition metal ion Inorganic materials 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- DJBWYWDKHVKANE-BYPYZUCNSA-N (2s)-2-(2,2-dimethylhydrazinyl)propanoic acid Chemical compound OC(=O)[C@H](C)NN(C)C DJBWYWDKHVKANE-BYPYZUCNSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- KHMYIIPFUJCUEK-UHFFFAOYSA-N 1-diethylphosphanylethyl(diethyl)phosphane Chemical compound CCP(CC)C(C)P(CC)CC KHMYIIPFUJCUEK-UHFFFAOYSA-N 0.000 description 1
- TZBZZWBYDXSQTP-UHFFFAOYSA-N 1-dimethylphosphanylethyl(dimethyl)phosphane Chemical compound CP(C)C(C)P(C)C TZBZZWBYDXSQTP-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- TXSVGHNFJXCOOD-UHFFFAOYSA-N 2-diethylphosphanylpropan-2-yl(diethyl)phosphane Chemical compound C(C)P(CC)C(C)(C)P(CC)CC TXSVGHNFJXCOOD-UHFFFAOYSA-N 0.000 description 1
- BUOTXFKBFYRTHP-UHFFFAOYSA-N 2-dimethylphosphanylpropan-2-yl(dimethyl)phosphane Chemical compound CP(C)C(C)(C)P(C)C BUOTXFKBFYRTHP-UHFFFAOYSA-N 0.000 description 1
- LRLQQERNMXHASR-UHFFFAOYSA-N 2-diphenylphosphanylpropan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 LRLQQERNMXHASR-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- IMBXXKBLDOWGPI-UHFFFAOYSA-N 2-n,3-n-bis(2,6-ditert-butylphenyl)butane-2,3-diimine Chemical compound CC(C)(C)C=1C=CC=C(C(C)(C)C)C=1N=C(C)C(C)=NC1=C(C(C)(C)C)C=CC=C1C(C)(C)C IMBXXKBLDOWGPI-UHFFFAOYSA-N 0.000 description 1
- KJMMITFGLXLELL-UHFFFAOYSA-N 2-n,3-n-bis(2-methylphenyl)butane-2,3-diimine Chemical compound C=1C=CC=C(C)C=1N=C(C)C(C)=NC1=CC=CC=C1C KJMMITFGLXLELL-UHFFFAOYSA-N 0.000 description 1
- YUFQUBWPYIPRHZ-UHFFFAOYSA-N 2-n,3-n-bis[2,6-di(propan-2-yl)phenyl]butane-2,3-diimine Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C(C)C(C)=NC1=C(C(C)C)C=CC=C1C(C)C YUFQUBWPYIPRHZ-UHFFFAOYSA-N 0.000 description 1
- QBMVJNBPZWJHTA-UHFFFAOYSA-N 2-n,3-n-di(propan-2-yl)butane-2,3-diimine Chemical compound CC(C)N=C(C)C(C)=NC(C)C QBMVJNBPZWJHTA-UHFFFAOYSA-N 0.000 description 1
- YVZSYWSEFSXJMH-UHFFFAOYSA-N 2-n,3-n-diethylbutane-2,3-diimine Chemical compound CCN=C(C)C(C)=NCC YVZSYWSEFSXJMH-UHFFFAOYSA-N 0.000 description 1
- KLYTUKWIWXAUFO-UHFFFAOYSA-N 2-n,3-n-diphenylbutane-2,3-diimine Chemical compound C=1C=CC=CC=1N=C(C)C(C)=NC1=CC=CC=C1 KLYTUKWIWXAUFO-UHFFFAOYSA-N 0.000 description 1
- OAQWHMYUSBYPOV-UHFFFAOYSA-N 2-n,3-n-ditert-butylbutane-2,3-diimine Chemical compound CC(C)(C)N=C(C)C(C)=NC(C)(C)C OAQWHMYUSBYPOV-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910017253 AsO Inorganic materials 0.000 description 1
- 229910017255 AsSe Inorganic materials 0.000 description 1
- 229910017259 AsTe Inorganic materials 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 1
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 1
- 229910018321 SbTe Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- YPKCXURFKBPRAY-UHFFFAOYSA-N diethylphosphanylmethyl(diethyl)phosphane Chemical compound CCP(CC)CP(CC)CC YPKCXURFKBPRAY-UHFFFAOYSA-N 0.000 description 1
- 108700003601 dimethylglycine Proteins 0.000 description 1
- MRNJHNUEBDGNEL-UHFFFAOYSA-N dimethylphosphanylmethyl(dimethyl)phosphane Chemical compound CP(C)CP(C)C MRNJHNUEBDGNEL-UHFFFAOYSA-N 0.000 description 1
- CANPJTMVPQIKCB-UHFFFAOYSA-N ditert-butyl(1-ditert-butylphosphanylethyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)P(C(C)(C)C)C(C)(C)C CANPJTMVPQIKCB-UHFFFAOYSA-N 0.000 description 1
- WBMJFMFJCWPAIT-UHFFFAOYSA-N ditert-butyl(ditert-butylphosphanylmethyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CP(C(C)(C)C)C(C)(C)C WBMJFMFJCWPAIT-UHFFFAOYSA-N 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- XULHHXCGBHJODI-UHFFFAOYSA-N iridium(3+);hydrate Chemical compound O.[Ir+3] XULHHXCGBHJODI-UHFFFAOYSA-N 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- DNQDRIBUHNACIY-UHFFFAOYSA-N n,n'-bis(2-methylphenyl)ethane-1,2-diimine Chemical compound CC1=CC=CC=C1N=CC=NC1=CC=CC=C1C DNQDRIBUHNACIY-UHFFFAOYSA-N 0.000 description 1
- JWVIIGXMTONOFR-UHFFFAOYSA-N n,n'-bis[2,6-di(propan-2-yl)phenyl]ethane-1,2-diimine Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=CC=NC1=C(C(C)C)C=CC=C1C(C)C JWVIIGXMTONOFR-UHFFFAOYSA-N 0.000 description 1
- DTJSYSWZBHHPJA-UHFFFAOYSA-N n,n'-di(propan-2-yl)ethane-1,2-diimine Chemical compound CC(C)N=CC=NC(C)C DTJSYSWZBHHPJA-UHFFFAOYSA-N 0.000 description 1
- FVHYOVFCJQRHGS-UHFFFAOYSA-N n,n'-diethylethane-1,2-diimine Chemical compound CCN=CC=NCC FVHYOVFCJQRHGS-UHFFFAOYSA-N 0.000 description 1
- YRHYXWGIOLWSEI-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diimine Chemical compound CN=CC=NC YRHYXWGIOLWSEI-UHFFFAOYSA-N 0.000 description 1
- QAHVEIHCWHKZET-UHFFFAOYSA-N n,n'-diphenylethane-1,2-diimine Chemical compound C=1C=CC=CC=1N=CC=NC1=CC=CC=C1 QAHVEIHCWHKZET-UHFFFAOYSA-N 0.000 description 1
- HACCVLBYBQLWMC-UHFFFAOYSA-N n,n'-ditert-butylethane-1,2-diimine Chemical compound CC(C)(C)N=CC=NC(C)(C)C HACCVLBYBQLWMC-UHFFFAOYSA-N 0.000 description 1
- HLGUAVMAMZECCK-UHFFFAOYSA-N n-(2-methylphenyl)-1-pyridin-2-ylethanimine Chemical compound C=1C=CC=NC=1C(C)=NC1=CC=CC=C1C HLGUAVMAMZECCK-UHFFFAOYSA-N 0.000 description 1
- CSUIUYZOXBBXSS-UHFFFAOYSA-N n-[2,6-di(propan-2-yl)phenyl]-1-pyridin-2-ylethanimine Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C(C)C1=CC=CC=N1 CSUIUYZOXBBXSS-UHFFFAOYSA-N 0.000 description 1
- DABHMSHNJTUDIQ-UHFFFAOYSA-N n-ethyl-1-pyridin-2-ylethanimine Chemical compound CCN=C(C)C1=CC=CC=N1 DABHMSHNJTUDIQ-UHFFFAOYSA-N 0.000 description 1
- IHOSZVRZVKLCSX-UHFFFAOYSA-N n-methyl-1-pyridin-2-ylethanimine Chemical compound CN=C(C)C1=CC=CC=N1 IHOSZVRZVKLCSX-UHFFFAOYSA-N 0.000 description 1
- HCTDPWPGLGTNPF-UHFFFAOYSA-N n-methylbutan-1-imine Chemical compound CCCC=NC HCTDPWPGLGTNPF-UHFFFAOYSA-N 0.000 description 1
- LTJMAOIYDHFJAF-UHFFFAOYSA-N n-phenyl-1-pyridin-2-ylethanimine Chemical compound C=1C=CC=NC=1C(C)=NC1=CC=CC=C1 LTJMAOIYDHFJAF-UHFFFAOYSA-N 0.000 description 1
- PEQAWYOTEKRNSA-UHFFFAOYSA-N n-tert-butyl-1-pyridin-2-ylethanimine Chemical compound CC(C)(C)N=C(C)C1=CC=CC=N1 PEQAWYOTEKRNSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 235000020573 organic concentrate Nutrition 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
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- UNQNIRQQBJCMQR-UHFFFAOYSA-N phosphorine Chemical compound C1=CC=PC=C1 UNQNIRQQBJCMQR-UHFFFAOYSA-N 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMLDUMMLRZFROX-UHFFFAOYSA-N pyridin-2-ylboronic acid Chemical compound OB(O)C1=CC=CC=N1 UMLDUMMLRZFROX-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052957 realgar Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005287 template synthesis Methods 0.000 description 1
- UTLODFUDVKXUIW-UHFFFAOYSA-N tert-butyl(2-tert-butylphosphanylpropan-2-yl)phosphane Chemical compound C(C)(C)(C)PC(C)(C)PC(C)(C)C UTLODFUDVKXUIW-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
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- 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
-
- 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
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- 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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
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- Y02E10/549—Organic PV cells
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- Electroluminescent Light Sources (AREA)
- Pyridine Compounds (AREA)
Description
ここでの部分配位子L1は式(3)に従い
部分配位子L2は1以上のドナー原子と2ないし40のC原子とを含むドナー配位子であり、ただし部分配位子L2はともに金属に結合した2つの環または部分環によって構成されず;
部分配位子L3は部分配位子L1または部分配位子L2と同一または異なる、
金属錯体に関する。
Mは各々の出現について同一または異なり、遷移金属であり、
Eは各々の出現について同一または異なり、C、NまたはPであり、
Qは各々の出現について同一または異なり、O、S、Se、TeまたはNであり、
Tは各々の出現について同一または異なり、N、PまたはCであり、
Xは各々の出現について同一または異なり、CR、NまたはPであり、
Yは各々の出現について同一または異なり、NR1、O、S、Se、Te、SO、SeO、TeO、SO2、SeO2、TeO2、R1SO、R1SeO、R1TeO、R1SO2、R1SeO2、R1TeO2、R1POまたは(R1)2POであり、
Vは各々の出現について同一または異なり、B、BR-、B(CR2)3、RB(CR2)3 -、B(O)3、RB(O)3 -、B(CR2CR2)3、RB(CR2CR2)3 -、B(CR2O)3、RB(CR2O)3 -、B(OCR2)3、RB(OCR2)3 -、Al(O)3、RAl(O)3 -、Al(OCR2)3、RAl(OCR2)3 -、CR、CO-、CN(R1)2、RC(CR2)3、RC(O)3、RC(CR2CR2)3、RC(CR2O)3、RC(OCR2)3、RC(SiR2)3、RC(SiR2CR2)3、RC(CR2SiR2)3、RC(SiR2SiR2)3、SiR、RSi(CR2)3、RSi(O)3、RSi(CR2CR2)3、RSi(OCR2)3、RSi(CR2O)3、RSi(SiR2)3、RSi(SiR2CR2)3、RSi(CR2SiR2)3、RSi(SiR2SiR2)3、N、NO、NR+、N(CR2)3、RN(CR2)3 +、N(C=O)3、N(CR2CR2)3、RN(CR2CR2)+、P、PO、PS、PSe、PTe、P(O)3、PO(O)3、P(OCR2)3、PO(OCR2)3、P(CR2)3、PO(CR2)3、P(CR2CR2)3、PO(CR2CR2)3、As、AsO、AsS、AsSe、AsTe、As(O)3、AsO(O)3、As(OCR2)3、AsO(OCR2)3、As(CR2)3、AsO(CR2)3、As(CR2CR2)3、AsO(CR2CR2)3、Sb、SbO、SbS、SbSe、SbTe、Sb(O)3、SbO(O)3、Sb(OCR2)3、SbO(OCR2)3、Sb(CR2)3、SbO(CR2)3、Sb(CR2CR2)3、SbO(CR2CR2)3、Bi、BiO、BiS、BiSe、BiTe、Bi(O)3、BiO(O)3、Bi(OCR2)3、BiO(OCR2)3、Bi(CR2)3、BiO(CR2)3、Bi(CR2CR2)3、BiO(CR2CR2)3、S+、S(CR2)3 +、S(CR2CR2)3 +、Se+、Se(CR2)3 +、Se(CR2CR2)3 +、Te+、Te(CR2)3 +、Te(CR2CR2)3 +または対応する非対称類似体または式(17)または式(18)の単位であり、
Rは各々の出現について同一または異なり、H、F、Cl、Br、I、NO2、CN、1ないし20のC原子を有する直鎖、分枝鎖または環状アルキルまたはアルコキシ基であり、その1以上の非隣接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−により置換され得るものであり、1以上のH原子はF、または1ないし14のC原子を有するアリール、アリールオキシまたはヘテロアリール基(これは1以上の非芳香族基Rにより置換され得る)または6ないし20のC原子を有するジアリールアミノ基(これは1以上の非芳香族置換基Rにより置換され得る)により置換され得るものであり、ともに同一環にも2つの異なる環にもあるここでの複数の置換基Rはともにさらなる単環式、多環式、脂肪族、芳香族および/またはベンゾ縮合環構造を形成し得るものであり、
R1は各々の出現について同一または異なり、Hまたは1ないし20のC原子を有する脂肪族または芳香族炭化水素基であり、
cは各々の出現について同一または異なり、0または1である)。
Mは各々の出現について同一または異なり、遷移金属イオンであり、
Halは各々の出現について同一または異なり、F、Cl、BrまたはIであり、
Aは各々の出現について同一または異なり、中性または1価アニオン性、単一座または二座配位子であり、
pは各々の出現について同一または異なり、1、2、3、4または5であり、その場合式(19)および(21)のpは金属Mの価数を示し、
qは各々の出現について同一または異なり、0、1、2、3または4であり、
式(20)の化合物もまた電荷を有しうるものであり、対イオンも含み、他の記号は上述したのと同一の意味を有する)。
以下の合成は、別段の指示が無ければ保護ガス雰囲気の下で実施された。出発材料は、ALDRICH、ABCR(溶媒、無機物、テトラヒドリドホウ酸ナトリウム、トリ−o−トリルホスフィン、6−クロロ−2−ピリジンカルボン酸)またはLancaster(ピナコリルピリジン−2−ボロネート)またはHeraeus(塩化イリジウム(III)水和物)から購入された。ビス(3−ブロモベンジル)ケトンを文献の方法(H.Sauriat−Dorizonら、J.Org.Chem.2003,68,240)により調製した。
例4に記載したイリジウム錯体(分子量677.4g/mol)を340℃、真空中で昇華させた。昇華は残渣を残すことなく進行し、HPLCで調べると分解の兆候はなかった。密封したアンプル中での340℃、160時間の貯蔵実験は、同様に、例4によるイリジウム錯体の熱誘起分解の兆候を示していなかった。比較によれば、WO02/015645による類似の非多座イリジウム錯体(CAS:376367−93−0、先行技術による比較例、分子量=694.7g/mol)はかなり熱安定性が低い(フェニルピリジン配位子へのフッ素の導入は、熱安定性に対して有益な効果を有すると主張されているが)。この錯体(1H−NMRおよびHPLCによれば99.9%を超える初期純度を有する)をT=340℃、p=5×10-5mbarで昇華すると、2時間後、以下を示した。
−約83重量%の黄色昇華物、
−約7重量%の有機濃縮物、特に、ピリジン−2−カルボン酸(1H−NMRで決定)を含む。
Claims (12)
- 式(1)の電気的に中性な金属錯体であって、
Cy1およびCy2は置換または非置換の芳香族基であり、Cy1はCy2と異なり、2つの環の一方が金属−炭素結合を介してイリジウムに結合し、他方が炭素と異なるドナー原子を介してイリジウムに結合し、
基Cy1およびCy2は共有結合を介して互いに結合し、さらに置換基を介して互いに結合して多環、脂肪族、または芳香族の環構造を形成していてもよく、
部分配位子Cy1−Cy2は金属Mおよび架橋単位Vとともに式(5)ないし(16)の部分構造を有する
Mはイリジウムであり、
EはCであり、
QはNであり、
TはNであり、
Xは各々の出現について同一または異なり、CRまたはPであり、
Vは各々の出現について同一または異なり、B、B(CR 2 ) 3 、B(O) 3 、CR、RC(CR 2 ) 3 、N、N(CR 2 ) 3 、N(C=O) 3 、P、PO、P(O) 3 、PO(O) 3 、P(CR 2 ) 3 、PO(CR 2 ) 3 、または式(17)または式(18)の単位であり、
Rは各々の出現について同一または異なり、H、F、Cl、Br、I、NO 2 、CN、1ないし20のC原子を有する直鎖、分枝鎖または環状アルキルまたはアルコキシ基であり、その1以上の非隣接CH 2 基は、−R 1 C=CR 1 −、−C≡C−、Si(R 1 ) 2 、Ge(R 1 ) 2 、Sn(R 1 ) 2 、C=O、C=S、C=Se、C=NR 1 、−O−、−S−、−NR 1 −または−CONR 1 −により置換され得るものであり、1以上のH原子はF、または1ないし14のC原子を有するアリール、アリールオキシまたはヘテロアリール基(それらは1以上の非芳香族基Rにより置換され得る)または6ないし20のC原子を有するジアリールアミノ基(それらは1以上の非芳香族基Rにより置換され得る)により置換され得るものであり、同一環上または異なる環上にある複数の置換基Rはともにさらなる単環式または多環式の、脂肪族、芳香族および/またはベンゾ縮合環構造を形成し得るものであり、
R 1 は各々の出現について同一または異なり、Hまたは1ないし20のC原子を有する脂肪族または芳香族炭化水素基であり、
cは0である)、
D1およびD2は各々の場合に同一または異なり、各々の場合に窒素、リン、酸素および硫黄から選択される1つのドナー原子を含むドナー基を表し、ドナー基D1およびD2は両方が環構造ではなく、両方が金属に結合し、ドナー基D1およびD2が芳香族窒素複素環、脂肪族アミン、脂肪族環状アミン、ニトリル、アミド、イミド、イミン、アルキル−、アリール−または混合アルキルアリールホスフィン、アルキル−、アリール−または混合アルキルアリールホスフィンハライド、アルキル、アリールまたは混合アルキルアリールホスファイト、ホスファ芳香族、アルコール、アルコレート、開環または環状エーテル、カルボニル基、ホスフィンオキシド基、スルホキシド基、カルボキシレート、フェノール、フェノレート、オキシム、ヒドロキサメート、β−ケトケトネート、β−ケトエステル、β−ジエステル、脂肪族または芳香族チオールおよびチオレート、開環または環状チオエーテル、チオフェン、チオカルボニル基、ホスフィンスルフィドまたはチオカルボキシレートであり、それらの各々はR基により置換され得るか、または置換されなくともよい)
金属錯体。 - Vが各々の出現について同一または異なり、CR、RC(CR2)3、RC(O)3、N、N(CR2)3、P、PO、P(O)3、PO(O)3、または式(17)または式(18)の基を表すことを特徴とする請求項1記載の金属錯体。
- Rが各々の出現について同一または異なり、H、F、Cl、Br、I、CN、1ないし6のC原子を有する直鎖、分枝鎖または環状アルキルまたはアルコキシ基、または3ないし8のC原子を有するアリール、アリールオキシまたはヘテロアリール基(1以上の非芳香族基Rにより置換され得る)または8ないし12のC原子を有するジアリールアミノ基(1以上の非芳香族基Rにより置換され得る)を表し、ここでの2以上の置換基Rは同一環にも2つの異なる環にもあり、ともに更なる単環式または多環式、脂肪族、芳香族および/またはベンゾ縮合環構造を形成し得ることを特徴とする請求項1記載の金属錯体。
- cが各々の出現について0に等しいことを特徴とする請求項1記載の金属錯体。
- 部分配位子D1−D2がβ−ケトケトネート、β−ケトエステル、β−ジエステル、ピリジルカルボキシレート、α−アミノ酸、イミノアセトアセトネート、ヒドロキサメート、ジホスフィン、ピリジルホスフィン、α−ホスフィノカルボキシレート、グリコールエーテル、エーテルアルコレート、ジアミン、イミン、ジイミン、アミノカルボン酸から誘導されるカルボキシレート、サリチルイミネート、ジアルコレート、ジチオレートであり、それらの各々がRにより置換されるか置換されていないことを特徴とする請求項1記載の金属錯体。
- 請求項1の式(4)の配位子またはその配位子の前駆体と、式(19)の金属アルコレート、式(20)の金属ケトケトネートまたは式(21)の金属ハライドとの反応による請求項1の式(1)の錯体の製造方法。
Mはイリジウムであり、
Halは各々の出現について同一または異なり、F、Cl、BrまたはIであり、
Aは各々の出現について同一または異なり、中性または1価アニオン性、単一座または二座配位子であり、
pは各々の出現について同一または異なり、1、2、3、4または5であり、その場合式(19)および(21)のpは金属Mの価数を示し、
qは各々の出現について同一または異なり、0、1、2、3または4であり、
式(20)の化合物もまた電荷を有しうるものであり、対イオンも含み、他の記号は請求項1に記載されているのと同一の意味を有する)。 - 反応が熱的、光化学的またはマイクロ波照射により活性化されることを特徴とする請求項6記載の方法。
- 有機電子部品における請求項1ないし5のいずれか1項記載の錯体の使用。
- 請求項1ないし5のいずれか1項記載の1以上の錯体を含む有機電子部品。
- 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(O−FET)、有機薄膜トランジスタ(O−TFT)、有機発光トランジスタ(O−LET)、有機太陽電池(O−SC)、有機光検出器、有機光レセプター、有機電界消光デバイス(O−FQD)または有機レーザーダイオード(O−レーザー)であることを特徴とする請求項11記載の有機電子部品。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011515423A (ja) * | 2008-03-25 | 2011-05-19 | メルク パテント ゲーエムベーハー | 金属錯体 |
Families Citing this family (83)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7993626B2 (en) * | 2007-01-11 | 2011-08-09 | Immunomedics, Inc. | Methods and compositions for F-18 labeling of proteins, peptides and other molecules |
US7597876B2 (en) * | 2007-01-11 | 2009-10-06 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
US7563433B2 (en) * | 2007-01-11 | 2009-07-21 | Immunomedics, Inc. | Methods and compositions for F-18 labeling of proteins, peptides and other molecules |
DE502005009868D1 (de) * | 2004-05-19 | 2010-08-19 | Merck Patent Gmbh | Metallkomplexe |
US20100219397A1 (en) * | 2005-08-05 | 2010-09-02 | Idemitsu Kosan Co., Ltd. | Transition metal complex compound and organic electroluminescent device using same |
DE102006054524B4 (de) * | 2006-11-20 | 2022-12-22 | Novaled Gmbh | Verwendung von Dithiolenübergangsmetallkomplexen und Selen- analoger Verbindungen als Dotand |
US8709382B2 (en) | 2007-01-11 | 2014-04-29 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
US8202509B2 (en) * | 2007-01-11 | 2012-06-19 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
US8153100B2 (en) * | 2007-01-11 | 2012-04-10 | Immunomedics, Inc. | Methods and compositions for F-18 labeling of proteins, peptides and other molecules |
US8889100B2 (en) | 2007-01-11 | 2014-11-18 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
US8545809B2 (en) | 2007-01-11 | 2013-10-01 | Immunomedics, Inc. | Methods and compositions for improved 18F labeling of proteins, peptides and other molecules |
US8398956B2 (en) | 2007-01-11 | 2013-03-19 | Immunomedics, Inc. | In vivo copper-free click chemistry for delivery of therapeutic and/or diagnostic agents |
DE102008027005A1 (de) | 2008-06-05 | 2009-12-10 | Merck Patent Gmbh | Organische elektronische Vorrichtung enthaltend Metallkomplexe |
DE102008036247A1 (de) * | 2008-08-04 | 2010-02-11 | Merck Patent Gmbh | Elektronische Vorrichtungen enthaltend Metallkomplexe |
DE102008063470A1 (de) | 2008-12-17 | 2010-07-01 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102008063490B4 (de) | 2008-12-17 | 2023-06-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung und Verfahren zum Einstellen des Farbortes einer weiß emittierenden Elektrolumineszenzvorrichtung |
DE102009007038A1 (de) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metallkomplexe |
DE102009009277B4 (de) | 2009-02-17 | 2023-12-07 | Merck Patent Gmbh | Organische elektronische Vorrichtung, Verfahren zu deren Herstellung und Verwendung von Verbindungen |
DE102009011223A1 (de) | 2009-03-02 | 2010-09-23 | Merck Patent Gmbh | Metallkomplexe |
DE102009012346B4 (de) | 2009-03-09 | 2024-02-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung und Verfahren zu deren Herstellung |
DE102009013041A1 (de) * | 2009-03-13 | 2010-09-16 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009014513A1 (de) | 2009-03-23 | 2010-09-30 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102009017064A1 (de) | 2009-04-09 | 2010-10-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
US20120104380A1 (en) | 2009-06-22 | 2012-05-03 | Merck Patent Gmbh | Conducting formulation |
DE102009041289A1 (de) | 2009-09-16 | 2011-03-17 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102009049587A1 (de) | 2009-10-16 | 2011-04-21 | Merck Patent Gmbh | Metallkomplexe |
JP5840621B2 (ja) | 2009-12-23 | 2016-01-06 | メルク パテント ゲーエムベーハー | 有機半導体化合物を含む組成物 |
KR20120115338A (ko) | 2009-12-23 | 2012-10-17 | 메르크 파텐트 게엠베하 | 중합체성 결합제를 포함하는 조성물 |
DE102010010481A1 (de) | 2010-03-06 | 2011-09-08 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
KR20130031827A (ko) | 2010-03-23 | 2013-03-29 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 재료 |
EP2559078A1 (en) | 2010-04-12 | 2013-02-20 | Merck Patent GmbH | Composition having improved performance |
CN102844902B (zh) | 2010-04-12 | 2016-06-08 | 默克专利有限公司 | 用于制备有机电子器件的组合物和方法 |
DE102010020044A1 (de) | 2010-05-11 | 2011-11-17 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
SG185680A1 (en) | 2010-05-27 | 2012-12-28 | Merck Patent Gmbh | Formulation and method for preparation of organic electronic devices |
DE112011102008B4 (de) * | 2010-06-15 | 2022-04-21 | Merck Patent Gmbh | Metallkomplexe |
DE112011102558B4 (de) | 2010-07-30 | 2022-01-05 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
DE102010048497A1 (de) | 2010-10-14 | 2012-04-19 | Merck Patent Gmbh | Formulierungen für organische Elektrolumineszenzvorrichtungen |
DE102010048498A1 (de) | 2010-10-14 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US9627626B2 (en) | 2011-01-13 | 2017-04-18 | Merck Patent Gmbh | Compounds for organic electroluminescent devices |
JP5747736B2 (ja) * | 2011-03-01 | 2015-07-15 | コニカミノルタ株式会社 | 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 |
CN103477462B (zh) | 2011-04-05 | 2016-05-25 | 默克专利有限公司 | 有机电致发光器件 |
CN103858249B (zh) | 2011-10-06 | 2017-10-17 | 默克专利有限公司 | 有机电致发光器件 |
JP5849853B2 (ja) * | 2012-05-10 | 2016-02-03 | コニカミノルタ株式会社 | 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 |
US9837622B2 (en) | 2012-07-13 | 2017-12-05 | Merck Patent Gmbh | Metal complexes |
EP2882763B1 (de) | 2012-08-07 | 2018-08-22 | Merck Patent GmbH | Metallkomplexe |
EP2712909A1 (en) | 2012-09-28 | 2014-04-02 | Solvay SA | Light emitting transition metal complexes based on hexadentate ligands |
US9793484B2 (en) | 2012-12-28 | 2017-10-17 | Merck Patent Gmbh | Composition comprising polymeric organic semiconducting compounds |
CN105793387B (zh) | 2013-12-06 | 2019-04-30 | 默克专利有限公司 | 含有包含丙烯酸酯和/或甲基丙烯酸酯单元的聚合物粘结剂的组合物 |
CN107406384B (zh) | 2014-12-04 | 2021-07-23 | 广州华睿光电材料有限公司 | 氘化的有机化合物、包含该化合物的混合物、组合物及有机电子器件 |
EP3229288B1 (en) | 2014-12-04 | 2019-05-01 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Polymer, and mixture, formulation and organic electronic device containing the same, and monomer thereof |
WO2016091219A1 (zh) | 2014-12-11 | 2016-06-16 | 广州华睿光电材料有限公司 | 有机化合物、包含其的混合物、组合物和有机电子器件 |
CN107108862B (zh) | 2015-01-13 | 2019-08-02 | 广州华睿光电材料有限公司 | 含乙炔基交联基团的共轭聚合物、包含其的混合物、组合物、有机电子器件及其应用 |
WO2016120007A1 (en) | 2015-01-30 | 2016-08-04 | Merck Patent Gmbh | Formulations with a low particle content |
JP6772188B2 (ja) | 2015-02-03 | 2020-10-21 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | 金属錯体 |
EP3323159B1 (en) | 2015-07-15 | 2023-01-04 | Merck Patent GmbH | Composition comprising organic semiconducting compounds |
CN105014885A (zh) * | 2015-08-20 | 2015-11-04 | 泰瑞机器股份有限公司 | 一种无流道切换阀内循环清料式螺杆柱塞塑料注射成型机 |
WO2017032439A1 (de) * | 2015-08-25 | 2017-03-02 | Merck Patent Gmbh | Metallkomplexe |
CN108291103B (zh) | 2015-11-12 | 2021-12-07 | 广州华睿光电材料有限公司 | 印刷组合物、包含其的电子器件及功能材料薄膜的制备方法 |
US10968243B2 (en) | 2015-12-04 | 2021-04-06 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organometallic complex and application thereof in electronic devices |
CN109415344B (zh) * | 2016-07-14 | 2022-06-03 | 默克专利有限公司 | 金属络合物 |
WO2018019688A1 (de) * | 2016-07-25 | 2018-02-01 | Merck Patent Gmbh | Metallkomplexe für den einsatz als emitter in organischen elektrolumineszenzvorrichtungen |
TW201817738A (zh) * | 2016-07-25 | 2018-05-16 | 德商麥克專利有限公司 | 金屬錯合物 |
KR101836041B1 (ko) * | 2016-08-30 | 2018-03-07 | 메르크 파텐트 게엠베하 | 금속 착물 |
EP3526227B1 (de) | 2016-10-12 | 2020-06-03 | Merck Patent GmbH | Binukleare metallkomplexe sowie elektronische vorrichtungen, insbesondere organische elektrolumineszenzvorrichtungen, enthaltend diese metallkomplexe |
KR102472249B1 (ko) * | 2016-10-13 | 2022-11-29 | 메르크 파텐트 게엠베하 | 금속 착물 |
CN109791992B (zh) | 2016-11-23 | 2021-07-23 | 广州华睿光电材料有限公司 | 高聚物、包含其的混合物、组合物和有机电子器件以及用于聚合的单体 |
CN109790459B (zh) | 2016-11-23 | 2022-08-12 | 广州华睿光电材料有限公司 | 有机化合物 |
WO2018095389A1 (zh) | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | 含氮稠杂环的化合物及其应用 |
US20190378991A1 (en) | 2016-11-23 | 2019-12-12 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Organic mixture, composition, and organic electronic component |
CN109790194B (zh) | 2016-11-23 | 2021-07-23 | 广州华睿光电材料有限公司 | 金属有机配合物、高聚物、组合物及有机电子器件 |
US11248138B2 (en) | 2016-11-23 | 2022-02-15 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Printing ink formulations, preparation methods and uses thereof |
US11239428B2 (en) | 2016-11-23 | 2022-02-01 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Boron-containing organic compound and applications thereof, organic mixture, and organic electronic device |
CN109790461B (zh) | 2016-12-08 | 2022-08-12 | 广州华睿光电材料有限公司 | 混合物、组合物及有机电子器件 |
CN109790118A (zh) | 2016-12-13 | 2019-05-21 | 广州华睿光电材料有限公司 | 共轭聚合物及其在有机电子器件的应用 |
WO2018114744A1 (en) | 2016-12-20 | 2018-06-28 | Merck Patent Gmbh | A white light emitting solid state light source |
US11289654B2 (en) | 2016-12-22 | 2022-03-29 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Polymers containing furanyl crosslinkable groups and uses thereof |
CN109792003B (zh) | 2016-12-22 | 2020-10-16 | 广州华睿光电材料有限公司 | 基于狄尔斯-阿尔德反应的可交联聚合物及其在有机电子器件中的应用 |
JP7053641B2 (ja) * | 2017-02-14 | 2022-04-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | オルト-メタル化金属錯体の調製方法 |
TWI813576B (zh) | 2017-07-03 | 2023-09-01 | 德商麥克專利有限公司 | 具有低含量苯酚類雜質的調配物 |
US11404651B2 (en) | 2017-12-14 | 2022-08-02 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Transition metal complex material and application thereof in electronic devices |
WO2019114608A1 (zh) | 2017-12-14 | 2019-06-20 | 广州华睿光电材料有限公司 | 过渡金属配合物、聚合物、混合物、组合物及其应用 |
CN111315721B (zh) | 2017-12-21 | 2023-06-06 | 广州华睿光电材料有限公司 | 有机混合物及其在有机电子器件中的应用 |
CN108529693A (zh) * | 2018-04-03 | 2018-09-14 | 岭南师范学院 | 一种肽功能化纳米钯及其制备方法 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
FR2624862B1 (fr) * | 1987-12-18 | 1990-06-08 | Oris Ind | Cryptates de terres rares, procedes d'obtention, intermediaires de synthese et application a titre de marqueurs fluorescents |
DE4111878A1 (de) | 1991-04-11 | 1992-10-15 | Wacker Chemie Gmbh | Leiterpolymere mit konjugierten doppelbindungen |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
DE4436773A1 (de) | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
DE69608446T3 (de) | 1995-07-28 | 2010-03-11 | Sumitomo Chemical Company, Ltd. | 2,7-aryl-9-substituierte fluorene und 9-substituierte fluorenoligomere und polymere |
DE19614971A1 (de) | 1996-04-17 | 1997-10-23 | Hoechst Ag | Polymere mit Spiroatomen und ihre Verwendung als Elektrolumineszenzmaterialien |
FR2768817B1 (fr) * | 1997-09-19 | 1999-12-10 | Cis Bio Int | Methode homogene pour la detection et/ou la determination de l'activite phosphorylante d'un materiel biologique |
DE19846766A1 (de) | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere, enthaltend spezielle Fluorenbausteine mit verbesserten Eigenschaften |
US6166172A (en) | 1999-02-10 | 2000-12-26 | Carnegie Mellon University | Method of forming poly-(3-substituted) thiophenes |
EP1889891B1 (en) | 2000-11-30 | 2017-11-22 | Canon Kabushiki Kaisha | Luminescence device and display apparatus |
DE10104426A1 (de) | 2001-02-01 | 2002-08-08 | Covion Organic Semiconductors | Verfahren zur Herstellung von hochreinen, tris-ortho-metallierten Organo-Iridium-Verbindungen |
CN101355141B (zh) | 2001-06-15 | 2012-02-29 | 佳能株式会社 | 有机电致发光元件 |
US6653654B1 (en) * | 2002-05-01 | 2003-11-25 | The University Of Hong Kong | Electroluminescent materials |
US6916554B2 (en) | 2002-11-06 | 2005-07-12 | The University Of Southern California | Organic light emitting materials and devices |
GB0226010D0 (en) | 2002-11-08 | 2002-12-18 | Cambridge Display Tech Ltd | Polymers for use in organic electroluminescent devices |
DE10304819A1 (de) | 2003-02-06 | 2004-08-19 | Covion Organic Semiconductors Gmbh | Carbazol-enthaltende konjugierte Polymere und Blends, deren Darstellung und Verwendung |
DE10314102A1 (de) | 2003-03-27 | 2004-10-14 | Covion Organic Semiconductors Gmbh | Verfahren zur Herstellung von hochreinen Organo-Iridium-Verbindungen |
DE10325820A1 (de) | 2003-06-07 | 2004-12-23 | Covion Organic Semiconductors Gmbh | Verfahren zur Herstellung von hochreinen, tris- und bis-ortho-metallierten Organometall-Verbindungen |
EP1491568A1 (en) | 2003-06-23 | 2004-12-29 | Covion Organic Semiconductors GmbH | Semiconductive Polymers |
DE10328627A1 (de) | 2003-06-26 | 2005-02-17 | Covion Organic Semiconductors Gmbh | Neue Materialien für die Elektrolumineszenz |
DE10337346A1 (de) | 2003-08-12 | 2005-03-31 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung |
DE102004003008A1 (de) | 2004-01-20 | 2005-10-06 | Covion Organic Semiconductors Gmbh | Neue Materialien für die Elektrolumineszenz und deren Verwendung |
DE502005009868D1 (de) | 2004-05-19 | 2010-08-19 | Merck Patent Gmbh | Metallkomplexe |
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TW200615277A (en) | 2006-05-16 |
KR20070032784A (ko) | 2007-03-22 |
EP1768989A1 (de) | 2007-04-04 |
US20080027220A1 (en) | 2008-01-31 |
CN1997656A (zh) | 2007-07-11 |
EP1768989B1 (de) | 2011-11-23 |
JP2008506652A (ja) | 2008-03-06 |
DE102004034517A1 (de) | 2006-02-16 |
KR20130032405A (ko) | 2013-04-01 |
KR101271826B1 (ko) | 2013-06-07 |
US7816531B2 (en) | 2010-10-19 |
ATE534653T1 (de) | 2011-12-15 |
WO2006008069A1 (de) | 2006-01-26 |
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