JP2014527033A - 光電子デバイス用の銅（ｉ）錯体 - Google Patents
光電子デバイス用の銅（ｉ）錯体 Download PDFInfo
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- JP2014527033A JP2014527033A JP2014517845A JP2014517845A JP2014527033A JP 2014527033 A JP2014527033 A JP 2014527033A JP 2014517845 A JP2014517845 A JP 2014517845A JP 2014517845 A JP2014517845 A JP 2014517845A JP 2014527033 A JP2014527033 A JP 2014527033A
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- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 230000005693 optoelectronics Effects 0.000 title claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- 125000001424 substituent group Chemical group 0.000 claims abstract description 51
- 125000003118 aryl group Chemical group 0.000 claims abstract description 45
- 239000003446 ligand Substances 0.000 claims abstract description 44
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 41
- 150000002367 halogens Chemical class 0.000 claims abstract description 41
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 40
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 40
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 27
- 239000010949 copper Substances 0.000 claims abstract description 21
- 125000004429 atom Chemical group 0.000 claims abstract description 17
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 11
- 230000005281 excited state Effects 0.000 claims abstract description 10
- 230000007935 neutral effect Effects 0.000 claims abstract description 9
- 239000012634 fragment Substances 0.000 claims abstract description 8
- 125000000962 organic group Chemical group 0.000 claims abstract description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
- 229910052802 copper Inorganic materials 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 230000008859 change Effects 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 23
- 125000000524 functional group Chemical group 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 19
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 238000006862 quantum yield reaction Methods 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000004020 conductor Substances 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000007942 carboxylates Chemical class 0.000 claims description 9
- 125000001033 ether group Chemical group 0.000 claims description 9
- -1 -OPh) Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 238000004020 luminiscence type Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910000077 silane Chemical group 0.000 claims description 5
- 230000005669 field effect Effects 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- 125000001317 arsoryl group Chemical group *[As](*)(*)=O 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000000061 phosphanyl group Chemical group [H]P([H])* 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 238000004246 ligand exchange chromatography Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 125000004665 trialkylsilyl group Chemical group 0.000 abstract 1
- 125000005106 triarylsilyl group Chemical group 0.000 abstract 1
- 238000000295 emission spectrum Methods 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 238000012512 characterization method Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001161 time-correlated single photon counting Methods 0.000 description 9
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- LZFDJHBNPWEXLK-UHFFFAOYSA-N [2-(2-diphenylphosphanyl-4-methylphenoxy)-5-methylphenyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C1=CC(C)=CC=C1OC1=CC=C(C)C=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 LZFDJHBNPWEXLK-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000006619 Stille reaction Methods 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- VTZVWRRQRAJARU-UHFFFAOYSA-N 4-phenyl-2-pyridin-2-yl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NC(C=1N=CC=CC=1)=N2 VTZVWRRQRAJARU-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003536 tetrazoles Chemical group 0.000 description 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
- LWAVGNJLLQSNNN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-azidobenzoate Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C(=O)ON1C(=O)CCC1=O LWAVGNJLLQSNNN-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 101100058670 Aeromonas hydrophila subsp. hydrophila (strain ATCC 7966 / DSM 30187 / BCRC 13018 / CCUG 14551 / JCM 1027 / KCTC 2358 / NCIMB 9240 / NCTC 8049) bsr gene Proteins 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical group 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 229920002601 oligoester Polymers 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000007704 wet chemistry method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5045—Complexes or chelates of phosphines with metallic compounds or metals
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
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Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11173371.3 | 2011-07-08 | ||
| EP11173371 | 2011-07-08 | ||
| EP11176760.4 | 2011-08-05 | ||
| EP11176760 | 2011-08-05 | ||
| EP11179112A EP2543673A1 (de) | 2011-07-08 | 2011-08-26 | Kupfer(I)komplexe für opto-elektronische Vorrichtungen |
| EP11179112.5 | 2011-08-26 | ||
| PCT/EP2012/063444 WO2013007707A1 (de) | 2011-07-08 | 2012-07-09 | Kupfer (i) komplexe für opto-elektronische vorrichtungen |
Publications (2)
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| JP2014527033A true JP2014527033A (ja) | 2014-10-09 |
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| EP (2) | EP2543673A1 (enExample) |
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| KR (1) | KR20140044904A (enExample) |
| CN (1) | CN103797017B (enExample) |
| WO (1) | WO2013007707A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2015037138A (ja) * | 2013-08-14 | 2015-02-23 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子用金属錯体、並びに表示装置及び照明装置 |
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|---|---|---|---|---|
| DE102009030475A1 (de) * | 2009-06-24 | 2011-01-05 | Hartmut Prof. Dr. Yersin | Kupfer-Komplexe für optoelektronische Anwendungen |
| DE102011089687A1 (de) * | 2011-12-22 | 2013-06-27 | Hartmut Yersin | Singulett-Harvesting mit speziellen organischen Molekülen ohne Metallzentren für opto-elektronische Vorrichtungen |
| US10347851B2 (en) | 2013-12-20 | 2019-07-09 | Udc Ireland Limited | Highly efficient OLED devices with very short decay times |
| DE102015216658A1 (de) | 2014-09-02 | 2016-03-03 | Cynora Gmbh | Strukturell Stabilisierte Kupfer(I)-Komplexe |
| EP2993176A1 (de) | 2014-09-02 | 2016-03-09 | cynora GmbH | Metall(i)-komplexe für verbesserte leitfähigkeit |
| WO2016037964A1 (de) | 2014-09-08 | 2016-03-17 | Cynora Gmbh | Verbesserte optisch aktive schicht und verfahren zur herstellung |
| EP3192107B1 (de) | 2014-09-08 | 2023-08-23 | Samsung Display Co., Ltd. | Stabilisierte optisch aktive schicht und verfahren zur herstellung |
| KR102460646B1 (ko) | 2014-09-16 | 2022-10-31 | 삼성디스플레이 주식회사 | 밝은 루미네선스에 적합한 발광층 |
| KR102556025B1 (ko) * | 2014-09-17 | 2023-07-19 | 삼성디스플레이 주식회사 | 유기금속 착체 및 이를 포함하는 유기 발광 소자 |
| WO2016079097A1 (de) * | 2014-11-18 | 2016-05-26 | Cynora Gmbh | Kupfer(i)komplexe für optoelektronische anwendungen |
| KR102471707B1 (ko) | 2015-06-03 | 2022-11-29 | 유디씨 아일랜드 리미티드 | 매우 짧은 붕괴 시간을 갖는 고효율 oled 소자 |
| CN105111459A (zh) * | 2015-09-24 | 2015-12-02 | 盐城工学院 | 基于3-abpt配体的Cu(I)配位聚合物及其制备方法 |
| CN107652326B (zh) * | 2017-10-31 | 2019-09-17 | 江西理工大学 | 一种间甲基吡啶四氮唑铜[i]配合物蓝光材料及其制备方法 |
| CN107722045B (zh) * | 2017-10-31 | 2019-09-24 | 江西理工大学 | 一种对甲基吡啶四氮唑铜[i]配合物蓝光材料及其制备方法 |
| PT3762368T (pt) | 2018-03-08 | 2022-05-06 | Incyte Corp | Compostos de aminopirazina diol como inibidores de pi3k-y |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| TW202030902A (zh) | 2018-09-12 | 2020-08-16 | 德商麥克專利有限公司 | 電致發光裝置 |
| EP3850055A1 (en) | 2018-09-12 | 2021-07-21 | Merck Patent GmbH | Materials for organic electroluminescent devices |
| TWI826522B (zh) | 2018-09-12 | 2023-12-21 | 德商麥克專利有限公司 | 電致發光裝置 |
| US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
| US12351594B2 (en) | 2019-04-11 | 2025-07-08 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| CN114641482A (zh) | 2019-11-04 | 2022-06-17 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
| TW202134252A (zh) | 2019-11-12 | 2021-09-16 | 德商麥克專利有限公司 | 有機電致發光裝置用材料 |
| TW202136181A (zh) | 2019-12-04 | 2021-10-01 | 德商麥克專利有限公司 | 有機電致發光裝置用的材料 |
| WO2021151922A1 (de) | 2020-01-29 | 2021-08-05 | Merck Patent Gmbh | Benzimidazol-derivate |
| EP4126884B1 (en) | 2020-03-23 | 2025-07-09 | Merck Patent GmbH | Materials for organic electroluminescent devices |
| KR102776384B1 (ko) | 2020-05-06 | 2025-03-10 | 삼성디스플레이 주식회사 | 발광 소자 및 이를 포함하는 전자 장치 |
| CN112358500A (zh) * | 2020-11-09 | 2021-02-12 | 江西科技师范大学 | 一种具有高摩尔吸光系数的Cu(I)配合物发光材料 |
| CN113416539B (zh) * | 2021-05-06 | 2022-03-22 | 北京师范大学 | 高量子产率可溶液加工的固体蓝色荧光-红色磷光碳量子有机框架及其制备和应用 |
| WO2024105066A1 (en) | 2022-11-17 | 2024-05-23 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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- 2012-07-09 KR KR1020147003327A patent/KR20140044904A/ko not_active Withdrawn
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2729477A1 (de) | 2014-05-14 |
| CN103797017A (zh) | 2014-05-14 |
| WO2013007707A1 (de) | 2013-01-17 |
| CN103797017B (zh) | 2017-02-15 |
| KR20140044904A (ko) | 2014-04-15 |
| US9266906B2 (en) | 2016-02-23 |
| EP2543673A1 (de) | 2013-01-09 |
| US20140235006A1 (en) | 2014-08-21 |
| EP2729477B1 (de) | 2016-01-20 |
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