JP2012512166A - イミダゾ[1,2−f]フェナントリジンイリジウム錯体に基づく高い効率を有する青色発光体 - Google Patents
イミダゾ[1,2−f]フェナントリジンイリジウム錯体に基づく高い効率を有する青色発光体 Download PDFInfo
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- JP2012512166A JP2012512166A JP2011540925A JP2011540925A JP2012512166A JP 2012512166 A JP2012512166 A JP 2012512166A JP 2011540925 A JP2011540925 A JP 2011540925A JP 2011540925 A JP2011540925 A JP 2011540925A JP 2012512166 A JP2012512166 A JP 2012512166A
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- RFTZGHDEWZCFGM-UHFFFAOYSA-N imidazo[1,2-f]phenanthridine;iridium Chemical compound [Ir].C1=CC=C2N3C=CN=C3C3=CC=CC=C3C2=C1 RFTZGHDEWZCFGM-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 71
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- 125000004429 atom Chemical group 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 239000003446 ligand Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 239000012044 organic layer Substances 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 239000002019 doping agent Substances 0.000 abstract description 20
- -1 imidazo [1,2-f] phenanthridine compound Chemical class 0.000 abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 105
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 88
- 239000010410 layer Substances 0.000 description 76
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000011541 reaction mixture Substances 0.000 description 57
- 239000000463 material Substances 0.000 description 47
- 239000000203 mixture Substances 0.000 description 42
- 239000000047 product Substances 0.000 description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- 238000005424 photoluminescence Methods 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 11
- 238000006862 quantum yield reaction Methods 0.000 description 11
- 230000001965 increasing effect Effects 0.000 description 10
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- PMWOFIVNSBKMRQ-UHFFFAOYSA-N 3h-imidazo[4,5-k]phenanthridine Chemical class C1=CC=C2C3=C(NC=N4)C4=CC=C3C=NC2=C1 PMWOFIVNSBKMRQ-UHFFFAOYSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- 229940062627 tribasic potassium phosphate Drugs 0.000 description 7
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000005401 electroluminescence Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 6
- 230000000670 limiting effect Effects 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 239000004576 sand Substances 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 6
- 230000032258 transport Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000012485 toluene extract Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 239000008241 heterogeneous mixture Substances 0.000 description 4
- 150000007857 hydrazones Chemical class 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000002883 imidazolyl group Chemical class 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- HLLGVBMZPQPUPZ-UHFFFAOYSA-N 2-(2,6-dibromophenyl)acetaldehyde Chemical compound BrC1=CC=CC(Br)=C1CC=O HLLGVBMZPQPUPZ-UHFFFAOYSA-N 0.000 description 2
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 2
- 101100232347 Mus musculus Il11ra1 gene Proteins 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- HDULBKVLSJEMGN-UHFFFAOYSA-N dicyclohexylphosphane Chemical compound C1CCCCC1PC1CCCCC1 HDULBKVLSJEMGN-UHFFFAOYSA-N 0.000 description 2
- SURBAJYBTYLRMQ-UHFFFAOYSA-N dioxido(propan-2-yloxy)borane Chemical compound CC(C)OB([O-])[O-] SURBAJYBTYLRMQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 201000001366 familial temporal lobe epilepsy 2 Diseases 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- SHWNDUJCIYUZRF-UHFFFAOYSA-N imidazo[1,2-f]phenanthridine Chemical class C1=CC=C2N3C=CN=C3C3=CC=CC=C3C2=C1 SHWNDUJCIYUZRF-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical group [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- CBQFZTHZVWFWIJ-UHFFFAOYSA-N 2,6-bis(prop-1-en-2-yl)-3h-imidazo[4,5-k]phenanthridine Chemical compound C1=CC=C2C3=C(NC(C(=C)C)=N4)C4=CC=C3C(C(C)=C)=NC2=C1 CBQFZTHZVWFWIJ-UHFFFAOYSA-N 0.000 description 1
- YDYNSAUGVGAOLO-UHFFFAOYSA-N 2,6-dibromobenzaldehyde Chemical compound BrC1=CC=CC(Br)=C1C=O YDYNSAUGVGAOLO-UHFFFAOYSA-N 0.000 description 1
- SKQNWSBNAIOCOC-UHFFFAOYSA-N 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC=C1C#N SKQNWSBNAIOCOC-UHFFFAOYSA-N 0.000 description 1
- QNZFUMVTUFOLRT-UHFFFAOYSA-N 2-(cyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CCCCC1 QNZFUMVTUFOLRT-UHFFFAOYSA-N 0.000 description 1
- KNPNXYYEHGTPCD-UHFFFAOYSA-N 2-bromo-2-(2,6-dibromophenyl)acetaldehyde Chemical compound O=CC(Br)C1=C(Br)C=CC=C1Br KNPNXYYEHGTPCD-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- ZAZPDOYUCVFPOI-UHFFFAOYSA-N 2-methylpropylboronic acid Chemical compound CC(C)CB(O)O ZAZPDOYUCVFPOI-UHFFFAOYSA-N 0.000 description 1
- MECCSFDHAVAAAW-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yl-1,3,2-dioxaborolane Chemical compound CC(C)B1OC(C)(C)C(C)(C)O1 MECCSFDHAVAAAW-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- HAUNPYVLVAIUOO-UHFFFAOYSA-N 4,4-dimethylcyclohex-2-en-1-one Chemical compound CC1(C)CCC(=O)C=C1 HAUNPYVLVAIUOO-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- PMVLECLDZQQHOD-UHFFFAOYSA-N Brc1cccc(Br)c1-c1cnc2[n]1c(cccc1)c1c1ccccc21 Chemical compound Brc1cccc(Br)c1-c1cnc2[n]1c(cccc1)c1c1ccccc21 PMVLECLDZQQHOD-UHFFFAOYSA-N 0.000 description 1
- COAOUZUIOBNWIN-UHFFFAOYSA-N C(CC1)CCC1c1c(-c2cnc3[n]2c2ccccc2c2c3cccc2)c(C2=CCCCC2)ccc1 Chemical compound C(CC1)CCC1c1c(-c2cnc3[n]2c2ccccc2c2c3cccc2)c(C2=CCCCC2)ccc1 COAOUZUIOBNWIN-UHFFFAOYSA-N 0.000 description 1
- WQXAQLNCEZKKKJ-UHFFFAOYSA-N C=[Br]c1cccc(Br)c1-c1cnc2[n]1c(cccc1)c1c1ccccc21 Chemical compound C=[Br]c1cccc(Br)c1-c1cnc2[n]1c(cccc1)c1c1ccccc21 WQXAQLNCEZKKKJ-UHFFFAOYSA-N 0.000 description 1
- UETUCBBTDAURFR-UHFFFAOYSA-O CC(C)(C(C)(C)OBC1=CCC(C)(C)CC1)[OH2+] Chemical compound CC(C)(C(C)(C)OBC1=CCC(C)(C)CC1)[OH2+] UETUCBBTDAURFR-UHFFFAOYSA-O 0.000 description 1
- BWZGUQVLYOYNKB-UHFFFAOYSA-N CC(C)Cc1cccc(CC(C)C)c1-c1cnc2[n]1c1ccccc1c1ccccc21 Chemical compound CC(C)Cc1cccc(CC(C)C)c1-c1cnc2[n]1c1ccccc1c1ccccc21 BWZGUQVLYOYNKB-UHFFFAOYSA-N 0.000 description 1
- PAGTVZVUWNLLPY-UHFFFAOYSA-N CC(C1c(c(Br)ccc2)c2Br)N=C2N1c(cccc1)c1-c1c2cccc1 Chemical compound CC(C1c(c(Br)ccc2)c2Br)N=C2N1c(cccc1)c1-c1c2cccc1 PAGTVZVUWNLLPY-UHFFFAOYSA-N 0.000 description 1
- AJCBNAXSCZNGET-UHFFFAOYSA-N CC1(C)C(CC(C2CCC(C)(C)CC2)C(c2cnc3[n]2c(cccc2)c2c2ccccc32)=C)C1 Chemical compound CC1(C)C(CC(C2CCC(C)(C)CC2)C(c2cnc3[n]2c(cccc2)c2c2ccccc32)=C)C1 AJCBNAXSCZNGET-UHFFFAOYSA-N 0.000 description 1
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- MWRUKHNDDKOJAC-UHFFFAOYSA-N CC1C2=CCCC1C(C)C1(C)OS2OC1(C)C Chemical compound CC1C2=CCCC1C(C)C1(C)OS2OC1(C)C MWRUKHNDDKOJAC-UHFFFAOYSA-N 0.000 description 1
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- XYZMWUNEGPSOQG-UHFFFAOYSA-N [SiH3]c1cccc(Br)c1-c1cnc2[n]1c1ccccc1c1c2CCC=C1 Chemical compound [SiH3]c1cccc(Br)c1-c1cnc2[n]1c1ccccc1c1c2CCC=C1 XYZMWUNEGPSOQG-UHFFFAOYSA-N 0.000 description 1
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- 125000002619 bicyclic group Chemical group 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
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- 238000010168 coupling process Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- GCUVBACNBHGZRS-UHFFFAOYSA-N cyclopenta-1,3-diene cyclopenta-2,4-dien-1-yl(diphenyl)phosphane iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.c1cc[c-](c1)P(c1ccccc1)c1ccccc1 GCUVBACNBHGZRS-UHFFFAOYSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000003230 hygroscopic agent Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 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
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 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
- 230000037361 pathway Effects 0.000 description 1
- FVCXJXKLDUJOFA-UHFFFAOYSA-N phenanthridin-6-amine Chemical compound C1=CC=C2C(N)=NC3=CC=CC=C3C2=C1 FVCXJXKLDUJOFA-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].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 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
及び、Baldoら,“Very high-efficiency green organic light-emitting devices based on electrophosphorescence”, Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999)(“Baldo-II”)、これらを参照により全体を援用する。燐光は、米国特許第7,279, 704号明細書の第5〜6欄により詳細に記載されており、これを参照により援用する。
(工程2)
全てのデバイス例は、高真空(<10-7 Torr)の熱蒸着によって作製した。アノード電極は1200Åのインジウム錫オキシド(ITO)である。カソードは10ÅのLiFとそれに続く1000ÅのAl(アルミニウム)からなる。全てのデバイスは作製後直ちに窒素グローブボックス(< 1 ppmのH2O及びO2)内でエポキシ樹脂を用いて封止したガラス蓋に密封し、吸湿剤をそのパッケージ内に組み込んだ。
Claims (17)
- 前記4個以上の原子を有するアルキルが、分岐状アルキルである、請求項1に記載の化合物。
- 前記4個以上の原子を有するアルキルが、環式アルキルである、請求項1に記載の化合物。
- 前記4個以上の原子を有するアルキルが、二環式アルキルである、請求項1に記載の化合物。
- 前記4個以上の原子を有するアルキルが、多環式アルキルである、請求項1に記載の化合物。
- 前記4個以上の原子を有するアルキルが、炭素原子のみを有する、請求項1に記載の化合物。
- 前記4個以上の原子を有するアルキルが、少なくとも1個の炭素原子、少なくとも1個の窒素原子、または少なくとも1個の硫黄原子を有するヘテロアルキルである、請求項1に記載の化合物。
- R1およびR2が同じである、請求項1に記載の化合物。
- R1およびR2が異なる、請求項1に記載の化合物。
- R1およびR2がアリールである、請求項1に記載の化合物。
- 第一のデバイスが、消費者製品である請求項15に記載のデバイス。
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US12/632,251 US8815415B2 (en) | 2008-12-12 | 2009-12-07 | Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes |
US12/632,251 | 2009-12-07 | ||
PCT/US2009/067687 WO2010068876A1 (en) | 2008-12-12 | 2009-12-11 | BLUE EMITTER WITH HIGH EFFICIENCY BASED ON IMIDAZO [1,2-f] PHENANTHRIDINE IRIDIUM COMPLEXES |
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JP2016100224A Active JP6506211B2 (ja) | 2008-12-12 | 2016-05-19 | イミダゾ[1,2−f]フェナントリジンイリジウム錯体に基づく高い効率を有する青色発光体 |
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JP2017195003A Active JP6586140B2 (ja) | 2008-12-12 | 2017-10-05 | イミダゾ[1,2−f]フェナントリジンイリジウム錯体に基づく高い効率を有する青色発光体 |
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Also Published As
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US20140319504A1 (en) | 2014-10-30 |
US8815415B2 (en) | 2014-08-26 |
CN102292409A (zh) | 2011-12-21 |
US10008678B2 (en) | 2018-06-26 |
JP6258570B2 (ja) | 2018-01-10 |
JP6506211B2 (ja) | 2019-04-24 |
TW201035092A (en) | 2010-10-01 |
TW201529575A (zh) | 2015-08-01 |
CN103896991B (zh) | 2017-07-28 |
EP3081617B1 (en) | 2017-11-15 |
WO2010068876A1 (en) | 2010-06-17 |
EP2382281B1 (en) | 2016-04-27 |
JP6763999B2 (ja) | 2020-09-30 |
JP6586140B2 (ja) | 2019-10-02 |
EP2382281A1 (en) | 2011-11-02 |
TWI580680B (zh) | 2017-05-01 |
JP2019140415A (ja) | 2019-08-22 |
KR101636100B1 (ko) | 2016-07-04 |
CN103896991A (zh) | 2014-07-02 |
JP2018003032A (ja) | 2018-01-11 |
TWI492945B (zh) | 2015-07-21 |
KR20110105800A (ko) | 2011-09-27 |
CN102292409B (zh) | 2014-04-30 |
US20100148663A1 (en) | 2010-06-17 |
JP2016155858A (ja) | 2016-09-01 |
EP3081617A1 (en) | 2016-10-19 |
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