JP6608873B2 - メチル−d3置換されたイリジウム錯体 - Google Patents
メチル−d3置換されたイリジウム錯体 Download PDFInfo
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- JP6608873B2 JP6608873B2 JP2017105379A JP2017105379A JP6608873B2 JP 6608873 B2 JP6608873 B2 JP 6608873B2 JP 2017105379 A JP2017105379 A JP 2017105379A JP 2017105379 A JP2017105379 A JP 2017105379A JP 6608873 B2 JP6608873 B2 JP 6608873B2
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- 229910052741 iridium Inorganic materials 0.000 title description 9
- 150000002503 iridium Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 178
- 239000003446 ligand Substances 0.000 claims description 101
- 239000010410 layer Substances 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 239000012044 organic layer Substances 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 238000006467 substitution reaction Methods 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- -1 arylkyl Chemical group 0.000 claims description 19
- 239000002019 doping agent Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 239000000463 material Substances 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 125000001424 substituent group Chemical group 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 229910052751 metal Inorganic materials 0.000 description 22
- 239000002184 metal Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
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- 239000000047 product Substances 0.000 description 21
- 229910052805 deuterium Inorganic materials 0.000 description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 10
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 8
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
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- 229940125851 compound 27 Drugs 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
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- 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 5
- 230000005693 optoelectronics Effects 0.000 description 5
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- 150000003852 triazoles Chemical class 0.000 description 5
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 3
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- KDFXAMVXNKMSBQ-UHFFFAOYSA-N iridium(3+);3-methyl-2-phenylpyridine Chemical compound [Ir+3].CC1=CC=CN=C1C1=CC=CC=C1.CC1=CC=CN=C1C1=CC=CC=C1.CC1=CC=CN=C1C1=CC=CC=C1 KDFXAMVXNKMSBQ-UHFFFAOYSA-N 0.000 description 3
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 2
- 0 *C(*)(c(c(-c1ccccc1)c1)cc(C(*2)=CC=CC=*c3ccc4)*1I15(*(c(O)ccc6)c6-c6c1cccc6)=C2*3c4-c1ccccc51)O Chemical compound *C(*)(c(c(-c1ccccc1)c1)cc(C(*2)=CC=CC=*c3ccc4)*1I15(*(c(O)ccc6)c6-c6c1cccc6)=C2*3c4-c1ccccc51)O 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- QIEABXIHCMILKG-UHFFFAOYSA-K iridium(3+);trifluoromethanesulfonate Chemical compound [Ir+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F QIEABXIHCMILKG-UHFFFAOYSA-K 0.000 description 2
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- INQOMBQAUSQDDS-FIBGUPNXSA-N trideuterio(iodo)methane Chemical compound [2H]C([2H])([2H])I INQOMBQAUSQDDS-FIBGUPNXSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- BIBHOVYJSQDOJX-FIBGUPNXSA-N 2-[2-phenyl-6-(trideuteriomethyl)phenyl]pyridine Chemical compound C1(=CC=CC=C1)C1=C(C(=CC=C1)C([2H])([2H])[2H])C1=NC=CC=C1 BIBHOVYJSQDOJX-FIBGUPNXSA-N 0.000 description 1
- XIYPPJVLAAXYAB-UHFFFAOYSA-N 2-bromo-6-phenylpyridine Chemical compound BrC1=CC=CC(C=2C=CC=CC=2)=N1 XIYPPJVLAAXYAB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
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- BJATUPPYBZHEIO-FIBGUPNXSA-N 2-phenyl-3-(trideuteriomethyl)pyridine Chemical compound [2H]C([2H])([2H])C1=CC=CN=C1C1=CC=CC=C1 BJATUPPYBZHEIO-FIBGUPNXSA-N 0.000 description 1
- GREMYQDDZRJQEG-FIBGUPNXSA-N 2-phenyl-6-(trideuteriomethyl)pyridine Chemical compound [2H]C([2H])([2H])C1=CC=CC(C=2C=CC=CC=2)=N1 GREMYQDDZRJQEG-FIBGUPNXSA-N 0.000 description 1
- VFNWGKHVTMJLDU-NIIDSAIPSA-N 3-bromo-2-phenylpyridine 2-phenyl-3-(trideuteriomethyl)pyridine Chemical compound BrC=1C(=NC=CC1)C1=CC=CC=C1.C(C=1C(=NC=CC1)C1=CC=CC=C1)([2H])([2H])[2H] VFNWGKHVTMJLDU-NIIDSAIPSA-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
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- 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
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
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- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
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- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
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- 125000003710 aryl alkyl group Chemical group 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound 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 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
- 239000002356 single layer Substances 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
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- 125000005580 triphenylene group Chemical group 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
- 238000003868 zero point energy Methods 0.000 description 1
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Description
本出願は、2009年4月28日に出願した米国仮出願No.61/173,346号、及び2010年4月27日に出願した米国出願No.12/768,068号に対する優先権を主張し、それらの開示を、その全体を参照により本明細書に明示して援用する。
下記構造を有する配位子を含む化合物。
R′1、R′2、R′3、R′4、R′5、及びR′6は、モノ、ジ、トリ、又はテトラ置換を表すことができ;R′1、R′2、R′3、R′4、R′5、及びR′6は独立に、水素、アルキル、及びアリールからなる群から選択される。さらに好ましくは、ホストはH1である。
一般にOLEDは、アノードとカソードの間に配置され且つこれらと電気的に接続された少なくとも1つの有機層を含む。電流が流された場合、その有機層(単数又は複数)中にアノードは正孔を注入し、カソードは電子を注入する。注入された正孔と電子は、それぞれ反対に帯電した電極に向かって移動する。同じ分子上に電子と正孔が局在した場合、励起エネルギー状態を有する、局在化した電子-正孔対である「励起子」が形成される。この励起子が発光機構によって緩和する時に光が発せられる。ある場合には、励起子はエキシマー又はエキシプレックス上に局在することもできる。非放射機構、例えば熱緩和も起こることがあるが、通常は好ましくないと考えられている。
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。リン光は、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。
式Iを有する配位子を含む化合物に対して好ましいと記載した芳香環、金属、及び置換基についての選択は、式Iを有する配位子を含む化合物を含むデバイスにおいて用いるためにも好ましい。これらの選択には、金属M、環A及び環B、並びに置換基RA、RB、A1、A2、B1、B2、R1、及びR2が含まれる。
凝縮管、窒素導入口、及び2つの密栓を備えた三ツ口の1L丸底フラスコ中、2,6-ジブロモピリジン(15.3 g, 64.58 mmol)、フェニルボロン酸(7.87 g, 64.58 mmol)、及び炭酸カリウム(17.58 g, 129.16 mmol)を、228 mLのジメトキシエタン及び150 mLの水に添加した。窒素をその混合物に直接15分間バブリングした。テトラキス(トリフェニルホスフィン)パラジウム(0)(1.85 g, 1.60 mmol)を添加し、反応混合物を加熱し還流させた。反応は3時間加熱後に完了した。それを室温まで冷やし、水及び酢酸エチルで希釈した。層を分離し、水層を酢酸エチルで抽出した。有機層を硫酸マグネシウム上で乾燥させ、濾過し、溶媒を蒸発させた。その物質を、2%酢酸エチル/ヘキサンで溶出するカラムクロマトグラフィーと、続いて150℃で生成物を集めるクーゲルロールを使用しての真空蒸留によって精製した。5.2gの生成物を得た(34%)。
滴下ロート、窒素導入口、及び密栓を備えた三ツ口の500mL丸底フラスコを、真空下でヒートガンで加熱することによって乾燥させた。冷却した乾燥フラスコに、2-ブロモ-6-フェニルピリジン(11.3 g, 48.27 mmol)と100mLの無水THFを添加した。その溶液をドライアイス/アセトン浴中で冷やし、ヨードメタン-d3を滴下により添加した(6 mL, 96.54 mmol)。その溶液を冷たいまま1時間撹拌し、夜通し室温まで温めておいた。それを水で希釈し、酢酸エチルで2回抽出した。有機層を硫酸マグネシウム上で乾燥させ、濾過し、溶媒を蒸発させた。粗物質をカラムクロマトグラフィーによって2%酢酸エチル/ヘキサンで2回溶出させて精製した。5.8gの2-フェニル-6-メチル-d3-ピリジンを得た(70%)。
2-フェニル-6-メチル(d3)ピリジン(1.65 g, 9.58 mmol)、塩化イリジウム(1.6 g, 4.35 mmol)、及び30mLの2-エトキシエタノールの混合物を、夜通し、窒素下で加熱し還流させた。混合物を室温まで冷やし、赤色固体を濾過した。その固体をメタノール及びヘキサンで洗い、ドラフト内で空気乾燥させた。1.09gの生成物を得て(44%)、そのダイマーを次のステップにおいてそのまま用いた。
ダイマー(1.09 g, 0.956 mmol)及び125mLのジクロロメタンの混合物を250mLの丸底フラスコ中で調製した。その赤色混合物に10mLのメタノール中の銀トリフラート(0.51 g, 2.00 mmol)を添加し、混合物は緑色に変わった。フラスコの内容物を窒素下で室温にて夜通し撹拌した。この混合物をセライトパッドを通して濾過し、そのセライトをジクロロメタンで濯いだ。濾液を溶媒留去して緑黄色固体を得た。その固体を高真空下で乾燥させた。1gの固体を得て(71%)、次の反応にそのまま用いた。
50mLのガラスチューブ中に上記トリフラート錯体(1g, 1.3 mmol)及び2-フェニル-6-メチル(d3)ピリジン(0.7 g, 4.0 mmol)を添加し、そのチューブを脱気し、窒素で置換した。この方法を繰り返し、チューブを次に200℃にて窒素下で夜通し加熱した。チューブを冷やし、ジクロロメタンを添加して物質を溶かしてフラスコに移した。粗物質を20、40、及び50%ジクロロメタン/ヘキサンで溶出するカラムクロマトグラフィーによって精製し、次に250℃での昇華によって精製した。昇華後に0.58gの生成物を得た(63%)。
3-ブロモ-2-フェニルピリジン(9.9 g, 42 mmol)を100mLのテトラヒドロフランに溶かし、−78℃に冷やした。この溶液にBuLi(26.4 mL, ヘキサン中1.6 M)を滴下して添加した。添加の終了後、反応混合物を−78℃で1時間撹拌した。メチル-d3アイオダイド(9.3 g, 63 mmol)を添加し、2時間、室温に温めた。反応を次に水で停止させ、酢酸エチルで抽出した。粗生成物を、溶離液としてヘキサン及び酢酸エチルを用いるカラムによって精製した。2.3gの純粋な生成物が精製後に得られた。
3-メチル-d3-2-フェニルピリジン(1.8 g, 10.4 mmol)及びIr(acac)3(0.64g, 1.3 mmol)を260℃に、48時間、窒素下で加熱した。室温に冷やした後、ジクロロメタンを添加して生成物を溶かした。このジクロロメタン溶液をつぎにヘキサンに注いだ。沈殿物を集め、シリカゲル栓を通した。0.6gの生成物が得られた。この生成物を1,2-ジクロロベンゼンからの再結晶によってさらに精製した。
上記トリフラート錯体(1.4 g)、4-メチル-2,5-ジフェニルピリジン(1.5 g)、及び50mLのエタノールを混合し、窒素下で夜通し加熱して還流させた。沈殿物を濾過した。粗物質を50%ジクロロメタン/ヘキサンで溶出させるカラムクロマトグラフィーによって精製した。1.1gの所望の生成物が得られた。
上記イリジウムトリフラート錯体(1.0 g, 1.3 mmol)及び2-ビフェニル-4-メチルピリジン(1.0 g, 4 mmol)を100mLの丸底フラスコに入れた。20mLのエタノール及びメタノールの50:50溶液をそのフラスコに添加した。反応混合物を8時間還流させた。反応混合物を次に室温まで冷えるままにしておいた。反応混合物をシリカ栓の上に注ぎ、エタノール、次いでヘキサンで洗った。濾液を捨てた。その栓を次にジクロロメタンで洗い、生成物を溶出した。濾液から溶媒をロータリーエバポレーターで除去した。生成物を溶離液として50:50のジクロロメタン及びヘキサンを用いたカラムクロマトグラフィーを使用してさらに精製して0.5g(50%収率)の生成物を得た。
上記イリジウムトリフラート錯体(6.58 g, 9.2 mmol)及び4-(エチル,d3)-2,5-ジフェニルピリジン(6.58 g, 25.0 mmol)を1000mLの丸底フラスコに入れた。140mLのエタノール及びメタノールの50:50溶液をそのフラスコに添加した。反応混合物を8時間還流させた。反応混合物を次に室温まで冷えるままにしておいた。その反応混合物をシリカ栓上に注ぎ、エタノール、次にヘキサンで洗った。濾液は捨てた。その栓を次にジクロロメタンで洗って生成物を溶離させた。濾液から溶媒をロータリーエバポレーターで除去した。生成物を、溶離液として50:50のジクロロメタン及びヘキサンを用いたカラムクロマトグラフィーを使用してさらに精製して3.8g(54%)の生成物を得た。
全てのデバイスは、高真空下(<10-7 Torr)で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と次に1000ÅのAlからなる。全てのデバイスは作製後直ぐに窒素グローブボックス(<1 ppmのH2O及びO2)中でエポキシ樹脂を用いて封止したガラス蓋で密封し、水分吸収剤をそのパッケージに組み込んだ。
Claims (8)
- 下記構造を有する配位子を含む化合物からなる、有機発光デバイス用発光体。
R1、R2、R3、R4、R5、R6、R7、R8、及びR9のうち少なくとも1つが、CD 3 基、並びにCD 3 を有する、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アリールキル、アリール、及びヘテロアリール基からなる群から選択される基であり、
MはIrである。)
(但し、下記式:
- 下記構造を有する配位子を含む化合物からなる、有機発光デバイス用発光体。
R1、R2、R3、R4、R5、R6、R7、R8、及びR9のうち少なくとも1つがその化学構造中にCD、CD2、又はCD3 部分を有するアルキル基であり;
MはIrである。)
(但し、下記式:
- 有機発光デバイスの有機層において、請求項1〜4のいずれか一項に記載の有機発光デバイス用発光体を発光ドーパントとして用いる、使用方法。
- 有機発光デバイス用発光体を前記有機層においてホストと組み合わせて用いる、請求項5に記載の使用方法。
- 前記有機発光デバイスの有機層が発光層である、請求項5〜7のいずれか一項に記載の使用方法。
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