JP5215183B2 - 金属錯体 - Google Patents
金属錯体 Download PDFInfo
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- JP5215183B2 JP5215183B2 JP2008526396A JP2008526396A JP5215183B2 JP 5215183 B2 JP5215183 B2 JP 5215183B2 JP 2008526396 A JP2008526396 A JP 2008526396A JP 2008526396 A JP2008526396 A JP 2008526396A JP 5215183 B2 JP5215183 B2 JP 5215183B2
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- 150000004696 coordination complex Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 239000003446 ligand Substances 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052741 iridium Inorganic materials 0.000 claims description 13
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 abstract description 12
- 239000002184 metal Substances 0.000 abstract description 12
- 239000008204 material by function Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000013522 chelant Substances 0.000 description 11
- -1 s-pentyl group Chemical group 0.000 description 11
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000412 dendrimer Substances 0.000 description 9
- 229920000736 dendritic polymer Polymers 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 230000008021 deposition Effects 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000002466 imines Chemical class 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 CCC(CC)(*C1=C2****1)*(*)=C1C2=C(*=C)NC1(*)* Chemical compound CCC(CC)(*C1=C2****1)*(*)=C1C2=C(*=C)NC1(*)* 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- BGZHOUYGJXZNAI-UHFFFAOYSA-N 2-N,2-N,2-N',2-N',7-N,7-N,7-N',7-N'-octakis-phenyl-1,1'-spirobi[fluorene]-2,2',7,7'-tetramine Chemical compound C12=CC=C(N(C=3C=CC=CC=3)C=3C=CC=CC=3)C=C2C=C(C23C(=CC=C4C5=CC=C(C=C5C=C43)N(C=3C=CC=CC=3)C=3C=CC=CC=3)N(C=3C=CC=CC=3)C=3C=CC=CC=3)C1=CC=C2N(C=1C=CC=CC=1)C1=CC=CC=C1 BGZHOUYGJXZNAI-UHFFFAOYSA-N 0.000 description 2
- MTUBTKOZCCGPSU-UHFFFAOYSA-N 2-n-naphthalen-1-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 MTUBTKOZCCGPSU-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-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
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002504 iridium compounds Chemical class 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-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
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-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
- 238000001953 recrystallisation Methods 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- QQADCAPKFRAHQW-UHFFFAOYSA-N 1,2,5-thiadiazole;1,3,4-thiadiazole Chemical compound C=1C=NSN=1.C1=NN=CS1 QQADCAPKFRAHQW-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-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
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- HNFHVPDEAVTSAR-UHFFFAOYSA-N 1,5-diphenylpentane-2,4-dione Chemical compound C=1C=CC=CC=1CC(=O)CC(=O)CC1=CC=CC=C1 HNFHVPDEAVTSAR-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- IERDDDBDINUYCD-UHFFFAOYSA-N 1-[4-[4-(9h-carbazol-1-yl)phenyl]phenyl]-9h-carbazole Chemical group C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 IERDDDBDINUYCD-UHFFFAOYSA-N 0.000 description 1
- RJRXQRZUOOBXCR-UHFFFAOYSA-N 1-chloro-2-fluoronaphthalene Chemical compound C1=CC=CC2=C(Cl)C(F)=CC=C21 RJRXQRZUOOBXCR-UHFFFAOYSA-N 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
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- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
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- 239000012925 reference material Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Description
1.重大な欠陥は上記した化合物の低い熱的安定性である。例えば、ホモレプチック錯体であるfac−トリス(1−フェニルイソキノリン−C2,N)イリジウム(III)(Ir(piq)3)を分解することなく昇華させることができない。典型的な高い真空条件下(p<10-7mbar)でさえ、この化合物のかなりの分解が観察され、ここで、用いたIr(piq)3の量の約30重量%を占めるイリジウム含有灰に加えて、1−フェニルイソキノリンおよび他の低分子量化合物の遊離を検出することができる。この熱的分解は、再現することが実質的に不可能であるデバイス特性をもたらし、特に寿命に悪影響を与える。昇華による金属錯体の精製中に高い温度安定性が得られる錯体を有することも必要である。というのは、分解は錯体の大きな損失をもたらすからである。
2.動作寿命は一般的に余りにも低く、これまでは高品質で長寿命のデバイスへのリン光OLEDの導入を妨げてきた。
3.錯体はしばしば、有機溶媒への低い溶解度を有するにすぎず、これは再結晶またはクロマトグラフによる効率的な精製を非常に困難なものとするか、またはそれを妨げていた。このことは、特に、ディスプレイ製造において必要とされる比較的大量のものの精製にあてはまる。例えばポリマーの調製に用いられ得る臭素化錯体は特に低い溶解性を示すにすぎず、従って重合中に処理することが困難である。
4.従来技術に従う系のための配位子、特に赤色発光錯体のための配位子は複雑な、多工程のプロセスで得ることができるにすぎない。
(式中、以下が用いられる記号および添え字に適用される。すなわち、
Mは遷移金属であり、
Aは各々の出現について同一であるか異なり、NRまたはOであり、
Dは、A=NRの場合にはsp2混成炭素原子であり、これはMに結合し、またA=Oの場合には非結合電子対を有するヘテロ原子であり、これはMに配位し、
Eは各々の出現について同一であるか異なり、sp2混成炭素原子または窒素原子であり、
Cyは各々の出現について同一であるか異なり、同素環または複素環であり、これはsp2混成炭素原子または非結合電子対を有するヘテロ原子を介してMに結合しており、またこれには1つ以上のR基が任意に結合しており、
Yは、A=NRの場合には、各々の出現について同一であるか異なり、CR2、C(=O)、C(=NR)、C(=N−NR2)、C(=CR2)、SiR2、O、S、S(=O)、S(=O)2、Se、NR、PR、P(=O)R、AsR、As(=O)RまたはBRであり、A=Oの場合にはCR-であり、
R、R1は各々の出現について同一であるか異なり、H、F、Cl、Br、I、CN、B(OH)2、B(OR2)2、NO2、1〜40個のC原子を有する直鎖のアルキル基若しくはアルコキシ基、または3〜40個のC原子を有する分枝の若しくは環状のアルキル基若しくはアルコキシ基であり、ここで、1つ以上の非隣接のCH2基は、−R2C=CR2−、−C≡C−、Si(R2)2、Ge(R2)2、Sn(R2)2、−O−、−S−,−NR2−、−(C=O)−、−(C=NR2)−、−P=O(R2)−、または−CONR2−により置き換えられていてもよく、また1つ以上のH原子はF、Cl、Br若しくはIにより置き換えられていてもよく、または5〜40個のC原子を有する芳香族環系若しくは複素芳香族環系若しくはアリールオキシ基若しくはヘテロアリールオキシ基であり、これらは1つ以上の非芳香族基Rにより置換されていてもよく、ここでRはCyと共にさらなる脂肪族環系または芳香族環系を形成していてもよく、
R2は各々の出現について同一であるか異なり、Hまたは1〜20個のC原子を有する脂肪族炭化水素基又は芳香族炭化水素基であり、ここで個々のH原子はFにより置き換えられていてもよく、2つ以上のR2基は互いに環系を形成していてもよく、
nは1、2または3である)。
(式中、M、A、Y、R、R1、R2、L’、L’’、n、mおよびoは上記したものと同じ意味を有し、以下が他の記号には適用される:
Dは、A=NRの場合にはsp2混成炭素原子であり、これはMに結合し、またA=Oの場合には窒素またはリン、好ましくは窒素であり、これは非結合電子対によりMに配位しており、
Xは各々の出現について同一であるか異なり、CR1、NまたはPであり、または
(X−X)または(X=X)(すなわち、2つの隣り合うX)は、NR1、SまたはOを表し、または
(X−X)または(X=X)(すなわち、2つの隣り合うX)は、記号EがNを表す場合にはCR1、NまたはPを表し、但しCyは5員環または6員環を表し、
Eは各々の出現について同一であるか異なり、CまたはNであり、但し記号EがNを表す場合に、Cyにおける正確に1つの単位X−X(すなわち二つの隣り合うX)はCR1、NまたはPである)。
(式中、M、Y、D、R、R1、R2、L’’、n、mおよびoは上記したものと同じ意味を有し、さらに、
Xは各々の出現について同一であるか異なり、CR1またはNであり、または
(X−X)または(X=X)(すなわち、2つの隣り合うX)は、NR1、SまたはOを表し、但しCyは5員環または6員環を表し、
Qは各々の出現について同一であるか異なり、−CR1=CR1−、−N=CR1−、−N=N−、NR1、OまたはSである)。
Zは各々の出現について同一であるか異なり、二価の基である−C(R1)2−、−C(=O)−、−C[=C(R1)2]−、−C(R1)2−C(R1)2−、−C(R1)2−C(R1)2−C(R1)2−、−C(R1)2−O−C(R1)2−、−C(R1)2−N(R1)−、−C(R1)=C(R1)−、−C(R1)=N−、−O−、−S−、−N(R1)−、−P(R1)−、−P(=O)(R1)−または−B(R1)−である)。
1.本発明による化合物は、高い温度安定性により特徴づけられる。つまり、低分子量化合物は分解を伴わずに高真空下で蒸発させることができ、オリゴマー、デンドリマーおよびポリマー化合物も非常に熱的に安定であり、デバイスを損傷なく熱的に処理することを可能にする。この性質は、OLEDの再現性ある製造のための基本的な必要条件であり、特に、動作寿命に対して好ましい効果を有する。従って、これらレアメタルの化合物の資源保護的な利用がさらに可能である。というのは、錯体を精製中に実質的に全く損失なく昇華させることができるためである。
以下の合成を、他に示さない限り、保護ガス雰囲気下で行う。出発材料はアルドリッチまたはABCRから購入することができる。
本発明によるエレクトロルミネセンスデバイスを、例えばWO 05/003253に記載されるように製造することができる。2つの異なるOLEDについての結果をここで比較する。基本構造、用いた材料、ドープの程度、および層の厚さはより良い比較のために同一である。発光層におけるドーパントのみが異なる。例3は従来技術による比較標準を記載し、ここで発光層は、マトリックス材料CBPとゲスト材料であるトリス(フェニルイソキノリン)イリジウム(Ir(piq)3)から成る。マトリックス材料CBPとゲスト材料Ir1およびIr2から成る発光層を含むOLEDをさらに記載する(例4および5)。以下の構造を有するOLEDを上記した一般方法と同様にして製造する:
PEDOT 60nm(水からスピンコーティング;H.C.シュターク(Starck)、ゴスラーから購入したPEDOT;ポリ−[3,4−エチレンジオキシ−2,5−チオフェン])(HIL)
NaphDATA 20nm(蒸着;SynTecから購入したNaphDATA;4,4’,4’’−トリス(N−1−ナフチル−N−フェニルアミノ)トリフェニルアミン)(HTL)
S−TAD 20nm(蒸着;WO 99/12888に従って合成したS−TAD;2,2’,7,7’−テトラキス(ジフェニルアミノ)スピロビフルオレン)(HTL)
発光層:(EML)
CBP 20nm(蒸着;アルドリッチから購入したCBPをさらに精製し、最終的に2回昇華させる;4,4’−ビス(N−カルバゾリル)ビフェニル)
Ir1およびIr2 (10%ドープ、蒸着;例1および2に従って合成)
または
Ir(piq)3 (10%ドープ、蒸着;WO 03/0068526に従って合成)、比較例
BCP 10nm(蒸着;ABCRから購入したBCPをそのまま用いる;2,9−ジメチル−4,7−ジフェニル−1,10−フェナントロリン)(HBL)
AlQ3 10nm(蒸着;SynTecから購入したAlQ3;トリス(キノリナト)アルミニウム(III))(ETL)
LiF 1nm
Al 100nm。
本発明によるドーパントIr1およびIr2、および従来技術による比較材料Ir(piq)3を、WO 04/093207に記載されるマトリックス材料M1を含むOLEDにおいて試験する。以下の構造を有するOLEDを、例3〜5に記載した方法と同様にして製造する:
PEDOT 80nm(水からスピンコーティング;H.C.シュターク,ゴスラーから購入したPEDOT;ポリ−[3,4−エチレンジオキシ−2,5−チオフェン])(HIL)
NaphDATA 20nm(蒸着;SynTecから購入したNaphDATA;4,4’,4’’−トリス(N−1−ナフチル−N−フェニルアミノ)トリフェニルアミン)(HTL)
S−TAD 20nm(蒸着;WO 99/12888に従って合成したS−TAD;2,2’,7,7’−テトラキス(ジフェニルアミノ)スピロビフルオレン)(HTL)
発光層:(EML)
M1 ビス(9,9’−スピロビフルオレン−2−イル)ケトン(蒸着;WO 2004/093207に従って合成)
Ir1およびIr2(10%ドープ、蒸着;例1および2に従って合成)
または
Ir(piq)3 (10%ドープ、蒸着;WO 03/0068526に従って合成)
HBM1 2,7−ビス(4−ビフェニル−1−イル)−2’,7’−ジ−tert−ブチルスピロ−9,9’−ビフルオレン(蒸着;WO 05/011334に従って合成)
AlQ3 (蒸着;SynTecから購入したAlQ3;トリス(キノリナト)アルミニウム(III))(ETL)
Ba/Al 3nmのBa,この上に150nmのAl。
Claims (8)
- 式(1)
M(L)n(L’)m(L’’)o 式(1)
の化合物であって、
式(2b)
(式中、以下が用いられる記号および添え字に適用される:
Mはイリジウムである;
Yは、各々の出現について同一であるか異なり、CR2、C(=O)、またはC(=CR2)である;
Xは、各々の出現について同一であるか異なり、CR 1 またはNである;
R、R1は各々の出現について同一であるか異なり、H、F、1〜40個のC原子を有する直鎖のアルキル基、または1〜40個のC原子を有する分枝の若しくは環状のアルキル基であり、ここで、1つ以上の非隣接のCH2基は、−R2C=CR2 −によりそれぞれ置き換えられていてもよく、また1つ以上のH原子はFにより置き換えられていてもよく、または5〜40個のC原子を有する芳香族環系であり、これらは1〜40個のC原子を有するアルキル基により置換されていてもよく、さらに、RはR 1と共に5員環または6員環をさらに形成してもよい、
R2は各々の出現について同一であるか異なり、Hまたは1〜20個のC原子を有する脂肪族炭化水素基または芳香族炭化水素基であり、ここで個々のH原子はFにより置き換えられていてもよく、
nは1、2または3である;
式(1)の配位子L’は、以下の式の配位子である
DはNであり;
Qは各々の出現について同一であるか異なり、−CR 1 =CR 1 −、または−N=CR 1 −である)
式(1)の配位子L’’は、1,3−ジケトナート配位子である;mおよびoは各々の出現について同一であるか異なり、0、1または2である;n+m+o=3である)。 - 添え字n=2または3であることを特徴とする請求項1または2に記載の化合物。
- 記号X=CR1であることを特徴とする請求項1〜3のいずれか一項に記載の化合物。
- 構造(1)〜(33)から選択され、これらはR1により置換されているか、または置換されていないことを特徴とする請求項1〜4のいずれか一項に記載の化合物。
- 電子部品における発光化合物としての請求項1〜5のいずれか一項に記載の化合物の使用。
- 請求項1〜5のいずれか一項に記載の1種以上の化合物を含む電子部品。
- 有機およびポリマー発光ダイオード(OLED、PLED)、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)、有機集積回路(O−IC)、有機電界クエンチデバイス(organic field-quench device)(O−FQD)、有機発光トランジスタ(O−LET)、発光電気化学セル(LEC)、有機太陽電池(O−SC)、および有機レーザダイオード(O−laser)の群から選択される請求項7に記載の電子部品。
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Publication number | Priority date | Publication date | Assignee | Title |
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US7851579B2 (en) * | 2006-12-11 | 2010-12-14 | General Electric Company | Carbazolyl polymers for organic electronic devices |
CA2643394C (en) * | 2007-11-07 | 2013-12-31 | Chao-Jun Li | Ligands, their preparation and uses thereof in asymmetric reactions |
US10164284B2 (en) | 2012-07-27 | 2018-12-25 | Lockheed Martin Energy, Llc | Aqueous redox flow batteries featuring improved cell design characteristics |
US9559374B2 (en) | 2012-07-27 | 2017-01-31 | Lockheed Martin Advanced Energy Storage, Llc | Electrochemical energy storage systems and methods featuring large negative half-cell potentials |
US9692077B2 (en) | 2012-07-27 | 2017-06-27 | Lockheed Martin Advanced Energy Storage, Llc | Aqueous redox flow batteries comprising matched ionomer membranes |
US8753761B2 (en) | 2012-07-27 | 2014-06-17 | Sun Catalytix Corporation | Aqueous redox flow batteries comprising metal ligand coordination compounds |
US8691413B2 (en) | 2012-07-27 | 2014-04-08 | Sun Catalytix Corporation | Aqueous redox flow batteries featuring improved cell design characteristics |
US9768463B2 (en) | 2012-07-27 | 2017-09-19 | Lockheed Martin Advanced Energy Storage, Llc | Aqueous redox flow batteries comprising metal ligand coordination compounds |
US9382274B2 (en) | 2012-07-27 | 2016-07-05 | Lockheed Martin Advanced Energy Storage, Llc | Aqueous redox flow batteries featuring improved cell design characteristics |
US9865893B2 (en) | 2012-07-27 | 2018-01-09 | Lockheed Martin Advanced Energy Storage, Llc | Electrochemical energy storage systems and methods featuring optimal membrane systems |
US9899694B2 (en) | 2012-07-27 | 2018-02-20 | Lockheed Martin Advanced Energy Storage, Llc | Electrochemical energy storage systems and methods featuring high open circuit potential |
DK3224266T3 (da) | 2014-11-26 | 2021-04-26 | Lockheed Martin Energy Llc | Metalkomplekser af substituerede catecholater og redox flow-batterier indeholdende disse |
US10253051B2 (en) | 2015-03-16 | 2019-04-09 | Lockheed Martin Energy, Llc | Preparation of titanium catecholate complexes in aqueous solution using titanium tetrachloride or titanium oxychloride |
CN105070837A (zh) * | 2015-08-26 | 2015-11-18 | 电子科技大学 | 一种铱类配合物掺杂的三元太阳能电池 |
US10316047B2 (en) | 2016-03-03 | 2019-06-11 | Lockheed Martin Energy, Llc | Processes for forming coordination complexes containing monosulfonated catecholate ligands |
US10644342B2 (en) | 2016-03-03 | 2020-05-05 | Lockheed Martin Energy, Llc | Coordination complexes containing monosulfonated catecholate ligands and methods for producing the same |
US9938308B2 (en) | 2016-04-07 | 2018-04-10 | Lockheed Martin Energy, Llc | Coordination compounds having redox non-innocent ligands and flow batteries containing the same |
US10343964B2 (en) | 2016-07-26 | 2019-07-09 | Lockheed Martin Energy, Llc | Processes for forming titanium catechol complexes |
US10377687B2 (en) | 2016-07-26 | 2019-08-13 | Lockheed Martin Energy, Llc | Processes for forming titanium catechol complexes |
US10065977B2 (en) | 2016-10-19 | 2018-09-04 | Lockheed Martin Advanced Energy Storage, Llc | Concerted processes for forming 1,2,4-trihydroxybenzene from hydroquinone |
US10930937B2 (en) | 2016-11-23 | 2021-02-23 | Lockheed Martin Energy, Llc | Flow batteries incorporating active materials containing doubly bridged aromatic groups |
US10497958B2 (en) | 2016-12-14 | 2019-12-03 | Lockheed Martin Energy, Llc | Coordinatively unsaturated titanium catecholate complexes and processes associated therewith |
US10741864B2 (en) | 2016-12-30 | 2020-08-11 | Lockheed Martin Energy, Llc | Aqueous methods for forming titanium catecholate complexes and associated compositions |
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