JP2008523004A - 金属錯体 - Google Patents
金属錯体 Download PDFInfo
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- JP2008523004A JP2008523004A JP2007544802A JP2007544802A JP2008523004A JP 2008523004 A JP2008523004 A JP 2008523004A JP 2007544802 A JP2007544802 A JP 2007544802A JP 2007544802 A JP2007544802 A JP 2007544802A JP 2008523004 A JP2008523004 A JP 2008523004A
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- 150000004696 coordination complex Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 229920000642 polymer Polymers 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000003446 ligand Substances 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000000412 dendrimer Substances 0.000 claims description 16
- 229920000736 dendritic polymer Polymers 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000013522 chelant Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052741 iridium Inorganic materials 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 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
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 125000005842 heteroatom Chemical group 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
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 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
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229920000548 poly(silane) polymer 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
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 19
- -1 d 8 metal compounds Chemical class 0.000 description 17
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 9
- NDBCGHNTWCYIIU-UHFFFAOYSA-N iridium(3+);1-phenylisoquinoline Chemical compound [Ir+3].[C-]1=CC=CC=C1C1=NC=CC2=CC=CC=C12.[C-]1=CC=CC=C1C1=NC=CC2=CC=CC=C12.[C-]1=CC=CC=C1C1=NC=CC2=CC=CC=C12 NDBCGHNTWCYIIU-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000000746 purification Methods 0.000 description 7
- WJWVMGIAUYAQLA-UHFFFAOYSA-N 8-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CN=C12 WJWVMGIAUYAQLA-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 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
- 239000007983 Tris buffer Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYSIUCLUOYCUNJ-UHFFFAOYSA-N C1=CN=C2C(C3=C(C4(C)C)C=C(C)C=C3[Ir](C=3C5=C(C(C6=C5C5=NC=CC=C5C(C)=C6)(C)C)C=C(C)C=3)C=3C5=C(C(C6=C5C5=NC=CC=C5C(C)=C6)(C)C)C=C(C=3)C)=C4C=C(C)C2=C1 Chemical compound C1=CN=C2C(C3=C(C4(C)C)C=C(C)C=C3[Ir](C=3C5=C(C(C6=C5C5=NC=CC=C5C(C)=C6)(C)C)C=C(C)C=3)C=3C5=C(C(C6=C5C5=NC=CC=C5C(C)=C6)(C)C)C=C(C=3)C)=C4C=C(C)C2=C1 RYSIUCLUOYCUNJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 238000005859 coupling reaction Methods 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- KORCCDHCEDHFGR-UHFFFAOYSA-N 2,7,9,9-tetramethyl-4-nitrofluorene Chemical compound CC1(C)C2=CC(C)=CC=C2C2=C1C=C(C)C=C2[N+]([O-])=O KORCCDHCEDHFGR-UHFFFAOYSA-N 0.000 description 2
- FOABRMJMCJXPBW-UHFFFAOYSA-N 2,7,9,9-tetramethylfluoren-4-amine Chemical compound CC1=CC(N)=C2C3=CC=C(C)C=C3C(C)(C)C2=C1 FOABRMJMCJXPBW-UHFFFAOYSA-N 0.000 description 2
- VFHCPNLOWVCHGV-UHFFFAOYSA-N 2,7,9,9-tetramethylfluorene Chemical compound C1=C(C)C=C2C(C)(C)C3=CC(C)=CC=C3C2=C1 VFHCPNLOWVCHGV-UHFFFAOYSA-N 0.000 description 2
- LONBOJIXBFUBKQ-UHFFFAOYSA-N 2,7-dibromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC(Br)=CC=C3C2=C1 LONBOJIXBFUBKQ-UHFFFAOYSA-N 0.000 description 2
- 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
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- KPISENITDWIJME-UHFFFAOYSA-N 5,7,7,9-tetramethylindeno[2,1-h]quinoline Chemical compound C1=CC=NC2=C3C4=CC=C(C)C=C4C(C)(C)C3=CC(C)=C21 KPISENITDWIJME-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
- XUVGTJGSAXLLRK-UHFFFAOYSA-N 8-(2,4-difluorophenyl)quinoline Chemical compound FC1=CC(F)=CC=C1C1=CC=CC2=CC=CN=C12 XUVGTJGSAXLLRK-UHFFFAOYSA-N 0.000 description 2
- QPOSGTWVSDQBEV-UHFFFAOYSA-N 8-(3,5-difluorophenyl)quinoline Chemical compound FC1=CC(F)=CC(C=2C3=NC=CC=C3C=CC=2)=C1 QPOSGTWVSDQBEV-UHFFFAOYSA-N 0.000 description 2
- HKUZDMVANDXUSM-UHFFFAOYSA-N 8-(4-fluorophenyl)quinoline Chemical compound C1=CC(F)=CC=C1C1=CC=CC2=CC=CN=C12 HKUZDMVANDXUSM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 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
- 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
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 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
- 230000002349 favourable effect Effects 0.000 description 2
- 238000007306 functionalization reaction Methods 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
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
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- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 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 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000005610 quantum mechanics Effects 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
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Abstract
Description
Mは各々の出現について遷移金属であり、
Dは各々の出現について同一であるか異なり、それぞれ、Mに配位する非結合性の電子対を有するsp2混成のヘテロ原子であり、
Cは各々の出現についてMに結合するsp2混成炭素原子であり、
Eは各々の出現について同一であるか異なり、それぞれsp2混成炭素原子または窒素原子であり、
Zは各々の出現について同一であるか異なり、それぞれC(R)2またはNRであり、
Cy1は各々の出現について同一であるか異なり、それぞれ、sp2混成炭素原子を介してMに結合し、且つR基への結合を有していてもよい同素環または複素環であり、
Cy2は各々の出現について同一であるか異なり、それぞれ、原子Dを介してMに配位し、且つR基への結合を有していてもよい複素環であり、
Rは各々の出現について同一であるか異なり、それぞれ、H、F、CN、1〜40個の炭素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個の炭素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(ここで、いずれの場合においても1個以上の非隣接の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)−、SO、SO2または−CONR2−により置き換えられていてもよく、かつ1個以上のH原子はFにより置き換えられていてもよい)、または5〜40個の芳香族環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(これらは、1個以上の非芳香族R基により置換されていてもよい)、またはこれらの系の2つ、3つまたは4つの組み合わせであり、RはCy1および/またはCy2の一方または双方と共にさらなる脂肪族環系、芳香族環系、または複素芳香族環系を形成することも可能であり、
R2は各々の出現について同一であるか異なり、それぞれ、H、または1〜30個の炭素原子を有する脂肪族炭化水素基若しくは芳香族炭化水素基であり、
nは1、2または3である)
の基本構造M(L)nを含有する化合物
(ここで、式(1)における配位子L’およびL’’は、単座キレート配位子または二座キレート配位子であり、mおよびoは各々の出現について同一であるか異なり、それぞれ0、1または2であり、かつn+m+o=2または3である)
を提供する。
Mは各々の出現について、Mo、W、Re、Ru、Os、Rh、Ir、Pd、PtまたはAuであり、
Dは各々の出現について同一であるか異なり、それぞれ窒素またはリンであり、
Xは各々の出現について同一であるか異なり、それぞれCR1、NまたはPであるか、または
(X−X)または(X=X)(すなわち、2つの隣接するX基)は、NR1、S、またはOを表し、但し、Cy1およびCy2はそれぞれ、5員環または6員環を形成する、または
(X−X)または(X=X)(すなわち、2つの隣接するX基)は、対応する環における記号EがNを表す場合には、CR1、NまたはPを表し、
Eは各々の出現について同一であるか異なり、それぞれCまたはNであり、但し記号EがNを表す場合には、対応する環における正確に1つの単位X−X(すなわち、2つの隣接するX基)は、CR1、NまたはPであり、従って、その際環は5員環であり、
Rは既に定義した通りであり、かつXまたはR1と共に環系を形成していてもよく、
R1は各々の出現について同一であるか異なり、それぞれH、F、Cl、Br、I、OH、NO2、CN,N(R2)2、1〜40個の炭素原子を有する直鎖のアルキル基、アルコキシ基若しくはチオアルコキシ基、または3〜40個の炭素原子を有する分枝の若しくは環状のアルキル基、アルコキシ基若しくはチオアルコキシ基(ここで、1個以上の非隣接のCH2基は、−R2C=CR2−、−C≡C−、Si(R2)2、Ge(R2)2、Sn(R2)2、−O−、−S−、−NR2−、−(C=O)−、−(C=NR1)−、−P=O(R2)−、SO、SO2、−COOR2−、または−CONR2−により置き換えられていてもよく、かつ1個以上のH原子はF、Cl、Br、IまたはCNにより置き換えられていてもよい)、または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(これらは5〜40個の芳香族環原子を有し、かつ1個以上の非芳香族R1基により置換されていてもよい)、またはこれらの系の2つ、3つまたは4つの組み合わせであり、同じ環状または異なる環状の複数の置換基R1、またはR1およびRおよび/またはR2は、互いに、さらなる単環または多環の脂肪族環系または芳香族環系を形成していてもよい)。
(式中、M、D、R、R1、R2、L’’、n、mおよびoは上記に定義した通りであり、さらなる記号は以下の意味を有する。すなわち、
Xは各々の出現について同一であるか異なり、それぞれCR1、NまたはPであり、または
(X−X)または(X=X)(すなわち、2つの隣接するX基)は、NR1、SまたはOを示し、但しCy1およびCy2はそれぞれ、5員環または6員環であり、
Aは各々の出現について同一であるか異なり、それぞれ−CR1=CR1−、−N=CR1−、−P=CR1−、−N=N−、−P=N−、NR1、PR1、O、SまたはSeである)。
Yは各々の出現について同一であるか異なり、それぞれ、−C(R1)2−、−C(=O)−、−C[=C(R1)2]−、−C(R1)2−C(R1)2−、−C(=O)−O−、−C(=O)−N(R1)−、−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)−、および−B(R1)−の中から選択される)。
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社またはABCR社から購入することができる。2,7−ジブロモ−9,9−ジメチルフルオレンの合成は、EP 1298117 に記載される通りに行うことができ、8−キノリニルトリフルオロメタンスルホナートの合成は、Organometallics 2005, 24(6), 1329 に記載される通りに行うことができ、Na[Ir(acac)2Cl2]の合成は、WO 04/085449 に記載される通りに行うことができる。
a)8−(2,4−ジフルオロフェニル)キノリンの合成
a)8−(3,5−ジフルオロフェニル)キノリンの合成
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 に記載される通りに製造することができる。
NaphDATA 20nm(蒸着により付着;SynTec社から購入した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(蒸着により付着;WO 99/12888 に記載される通りに合成した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)
CPB 20nm(蒸着により付着;アルドリッチ社から入手し、さらに精製し、最後にさらに2回昇華させたCPB;4,4’−ビス(N−カルバゾリル)ビフェニル)
Ir1〜Ir5またはPt1 (10%ドーピング、蒸着により付着;例1〜6に記載される通りに合成)、または
Ir(piq)3 (10%ドーピング、蒸着により付着、WO 03/0068526 に記載される通りに合成),比較例
BCP 10nm(蒸着により付着;ABCR社から入手し、入手した物を用いた;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(蒸着により付着:SynTec社から入手したAlQ3;トリス(キノリナト)アルミニウム(III)),(ETL)
LiF 1nm
Al 100nm。
ドーパントIr(piq)3を用いて製造されるOLEDは、x=0.68、y=0.32のCIE色座標において上記した条件下で約6.5cd/Aの最大効率を典型的に与える。100cd/m2の基準輝度については6.2Vの電圧が必要である。500cd/m2の初期輝度における寿命は約250時間である(表1を参照のこと)。
本発明のドーパントIr1〜Ir5およびPt1、並びに従来技術による比較例Ir(piq)3を、WO 04/093207 に記載されてい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7〜13のものと同様の方法により製造した。
NaphDATA 20nm(蒸着により付着;SynTec社から入手した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(蒸着により付着;WO 99/12888 に記載される通りに合成した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(蒸着により付着、WO 2004/093207 に記載される通りに合成)
Ir1〜Ir5若しくはPt1 (10%ドーピング、蒸着により付着;例1〜6の通りに合成)、または
Ir(piq)3 (10%ドーピング、蒸着により付着;WO 03/0068526 に記載される通りに合成)
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(蒸着により付着;WO 05/011334 に記載される通りに合成)
AlQ3(蒸着により付着;SynTec社から入手した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 (22)
- 式(1)
M(L)n(L’)m(L’’)o 式(1)
の化合物であって、式(2)
Mは各々の出現について遷移金属であり、
Dは各々の出現について同一であるか異なり、それぞれMに配位する非結合性の電子対を有するsp2混成のヘテロ原子であり、
Cは各々の出現についてMに結合するsp2混成炭素原子であり、
Eは各々の出現について同一であるか異なり、それぞれsp2混成炭素原子または窒素原子であり、
Zは各々の出現について同一であるか異なり、それぞれC(R)2またはNRであり、
Cy1は各々の出現について同一であるか異なり、それぞれ、sp2混成炭素原子を介してMに結合し、且つR基への結合を有していてもよい同素環または複素環であり、
Cy2は各々の出現について同一であるか異なり、それぞれ、原子Dを介してMに配位し、且つR基への結合を有していてもよい複素環であり、
Rは各々の出現について同一であるか異なり、それぞれH、F、CN、1〜40個の炭素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個の炭素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(ここで、いずれの場合においても1個以上の非隣接の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)−、SO、SO2または−CONR2−により置き換えられていてもよく、かつ1個以上のH原子はFにより置き換えられていてもよい)、または5〜40個の芳香族環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(これらは、1個以上の非芳香族R基により置換されていてもよい)、またはこれらの系の2つ、3つまたは4つの組み合わせであり、RはCy1および/またはCy2の一方または双方と共にさらなる脂肪族環系、芳香族環系、または複素芳香族環系を形成することも可能であり、
R2は各々の出現について同一であるか異なり、それぞれ、H、または1〜20個の炭素原子を有する脂肪族炭化水素基若しくは芳香族炭化水素基であり、
nは1、2または3である)
の基本構造M(L)nを含有する化合物。
(ここで、式(1)における配位子L’およびL’’は、単座キレート配位子または二座キレート配位子であり、mおよびoは各々の出現について同一であるか異なり、それぞれ0、1または2であり、かつn+m+o=2または3である)。 - Cy1およびCy2は芳香族系または複素芳香族系であることを特徴とする請求項1に記載の化合物。
- 式(2a)
Mは各々の出現について、Mo、W、Re、Ru、Os、Rh、Ir、Pd、PtまたはAuであり、
Dは各々の出現について同一であるか異なり、それぞれ窒素またはリンであり、
Xは各々の出現について同一であるか異なり、それぞれCR1、NまたはPであるか、または
(X−X)または(X=X)(すなわち、2つの隣接するX基)は、NR1、S、またはOを表し、但し、Cy1およびCy2はそれぞれ、5員環または6員環を形成する、または
(X−X)または(X=X)(すなわち、2つの隣接するX基)は、対応する環における記号EがNを表す場合には、CR1、NまたはPを表し、
Eは各々の出現について同一であるか異なり、それぞれCまたはNであり、但し記号EがNを表す場合には、対応する環における正確に1つの単位X−X(すなわち、2つの隣接するX基)は、CR1、NまたはPであり、
Rは請求項1に定義した通りであり、かつXまたはR1と共に環系を形成していてもよく、
R1は各々の出現について同一であるか異なり、それぞれ、H、F、Cl、Br、I、OH、NO2、CN,N(R2)2、1〜40個の炭素原子を有する直鎖のアルキル基、アルコキシ基若しくはチオアルコキシ基、または3〜40個の炭素原子を有する分枝の若しくは環状のアルキル基、アルコキシ基若しくはチオアルコキシ基(ここで、1個以上の非隣接のCH2基は、−R2C=CR2−、−C≡C−、Si(R2)2、Ge(R2)2、Sn(R2)2、−O−、−S−、−NR2−、−(C=O)−、−(C=NR1)−、−P=O(R2)−、SO、SO2、−COOR2−、または−CONR2−により置き換えられていてもよく、かつ1個以上のH原子はF、Cl、Br、IまたはCNにより置き換えられていてもよい)、または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(これらは5〜40個の芳香族環原子を有し、かつ1個以上の非芳香族R1基により置換されていてもよい)、またはこれらの系の2つ、3つまたは4つの組み合わせであり、同じ環状または異なる環状の複数の置換基R1、またはR1およびRおよび/またはR2は、互いに、さらなる単環または多環の脂肪族環系または芳香族環系を形成していてもよい)
の基本構造M(L)nを含有する式(1)の請求項2に記載の化合物。 - 請求項3に記載の式(1a)の化合物
M(L)n(L’)m(L’’)o 式(1a)
であって、各々の出現について同一であるか異なる式(2b)の少なくとも1つの基本構造M(L)n
(式中、M、D、R、R1、R2、L’’、n、mおよびoは請求項1および3に定義した通りであり、さらなる記号は以下の意味を有する。すなわち、
Xは各々の出現について同一であるか異なり、それぞれCR1、NまたはPであり、または
(X−X)または(X=X)(すなわち、2つの隣接するX基)は、NR1、SまたはOを示し、
Aは各々の出現について同一であるか異なり、それぞれ、−CR1=CR1−、−N=CR1−、−P=CR1−、−N=N−、−P=N−、NR1、PR1、O、SまたはSeである)。 - 請求項1〜4の一項以上に記載の化合物であって、式(2c)、式(2d)または式(2e)の基本構造M(L)nを含有する化合物。
Yは各々の出現について同一であるか異なり、それぞれ、−C(R1)2−、−C(=O)−、−C[=C(R1)2]−、−C(R1)2−C(R1)2−、−C(=O)−O−、−C(=O)−N(R1)−、−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)−、および−B(R1)−の中から選択される)。 - モノアニオン性の二座配位子L’’が、1,3−ジケトンから誘導される1,3−ジケトナート、3−ケトエステルから誘導される3−ケトナート、アミノカルボン酸から誘導されるカルボキシラート、サリチルイミンから誘導されるサリチルイミナート(iminate)、および窒素含有複素環のホウ酸エステルから成る群から選択されることを特徴とする請求項1〜5の一項以上に記載の化合物。
- M=Rh、Ir、PdまたはPtであることを特徴とする請求項1〜6の一項以上に記載の化合物。
- n=2または3であることを特徴とする請求項1〜7の一項以上に記載の化合物。
- o=0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化合物。
- Z=C(R)2であることを特徴とする請求項1〜9の一項以上に記載の化合物。
- D=N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。
- X=CR1またはNであることを特徴とする請求項3〜11の一項以上に記載の化合物。
- 前記式(2c)、(2d)および(2e)における記号Yが、二価の基−(CR1)2−、−C(=O)−、−C(R1)2−C(R1)2−、−C(R1)2−N(R1)−、−C(R1)=C(R1)−、−C(R1)=N−、−O−、−S−または−N(R1)−を示すことを特徴とする請求項5〜12の一項以上に記載の化合物。
- 構造(1)〜(141)(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)の中から選択される請求項1〜13の一項以上に記載の化合物。
- 対応する遊離配位子と、アルコキシドおよび/またはハライドおよび/またはヒドロキシ、並びにケトケトナート基を有する金属化合物とを反応させることにより請求項1〜14の一項以上に記載の化合物を調製するための方法。
- 上記のRまたはR1基の少なくとも1つがポリマーまたはデンドリマーへの結合を示す請求項1〜14の一項以上に記載の化合物の1種以上を含む共役、部分共役若しくは非共役のオリゴマー、ポリマーまたはデンドリマー。
- 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、ポリケトン、ポリシラン若しくはポリチオフェン、またはこれらのタイプの種々の単位を含むコポリマーのクラスから選択されることを特徴とする請求項17に記載のオリゴマー、ポリマーまたはデンドリマー。
- 請求項1〜15の一項以上に記載の化合物が前記ポリマーの側鎖または主鎖中に取り込まれているか、または前記ポリマー鎖の分枝点若しくは前記ポリマー鎖の末端基に相当することを特徴とする請求項17および/または18に記載のオリゴマー、ポリマー、またはデンドリマー。
- 電子部品における活性要素としての、特に発光化合物としての請求項1〜14、および/または17〜19の一項以上に記載の化合物、オリゴマー、ポリマーまたはデンドリマーの使用。
- 請求項1〜14の一項以上に記載の1種以上の化合物、または請求項17〜19の一項以上に記載のオリゴマー、ポリマー若しくはデンドリマーを含む電子部品。
- 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)、有機太陽電池(O−SC)、有機発光トランジスタ(O−LET)、有機電界クエンチデバイス(organic field quench device)(O−FQD)、発光電気化学セル(LEC)、および有機レーザダイオード(O−laser)から成る群から選択される請求項21に記載の電子部品。
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TW200634020A (en) | 2006-10-01 |
JP5345322B2 (ja) | 2013-11-20 |
EP1820227A1 (de) | 2007-08-22 |
EP1820227B1 (de) | 2014-05-07 |
CN101073163A (zh) | 2007-11-14 |
CN100580972C (zh) | 2010-01-13 |
KR101288677B1 (ko) | 2013-07-22 |
WO2006061182A1 (de) | 2006-06-15 |
KR20070091139A (ko) | 2007-09-07 |
US8304542B2 (en) | 2012-11-06 |
US20090292080A1 (en) | 2009-11-26 |
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