JP5826630B2 - リン光性材料 - Google Patents
リン光性材料 Download PDFInfo
- Publication number
- JP5826630B2 JP5826630B2 JP2011526198A JP2011526198A JP5826630B2 JP 5826630 B2 JP5826630 B2 JP 5826630B2 JP 2011526198 A JP2011526198 A JP 2011526198A JP 2011526198 A JP2011526198 A JP 2011526198A JP 5826630 B2 JP5826630 B2 JP 5826630B2
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- Japan
- Prior art keywords
- group
- compound
- alkyl
- ring
- hydrogen
- Prior art date
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- 239000000463 material Substances 0.000 title description 58
- 150000001875 compounds Chemical class 0.000 claims description 312
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 162
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 143
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 138
- 125000003118 aryl group Chemical group 0.000 claims description 116
- 238000000034 method Methods 0.000 claims description 102
- 229910052757 nitrogen Inorganic materials 0.000 claims description 97
- 239000010410 layer Substances 0.000 claims description 93
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 239000003446 ligand Substances 0.000 claims description 81
- 239000012044 organic layer Substances 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 70
- 125000001424 substituent group Chemical group 0.000 claims description 70
- 125000001072 heteroaryl group Chemical group 0.000 claims description 57
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 37
- 125000000304 alkynyl group Chemical group 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 35
- 239000002019 doping agent Substances 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 238000009835 boiling Methods 0.000 claims description 27
- 238000006467 substitution reaction Methods 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 229910052741 iridium Inorganic materials 0.000 claims description 25
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- 125000002837 carbocyclic group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- -1 hexafluorophosphate Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 150000001721 carbon Chemical group 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
- 150000002500 ions Chemical class 0.000 claims description 13
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 12
- 230000007935 neutral effect Effects 0.000 claims description 11
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 9
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 9
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000005580 triphenylene group Chemical group 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical group FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 claims description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 252
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 240
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 127
- 239000000047 product Substances 0.000 description 120
- 239000000203 mixture Substances 0.000 description 119
- 230000015572 biosynthetic process Effects 0.000 description 97
- 238000003786 synthesis reaction Methods 0.000 description 97
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 59
- 239000011541 reaction mixture Substances 0.000 description 53
- 239000000243 solution Substances 0.000 description 53
- 239000000741 silica gel Substances 0.000 description 43
- 229910002027 silica gel Inorganic materials 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 238000000746 purification Methods 0.000 description 41
- 238000010992 reflux Methods 0.000 description 38
- 239000007787 solid Substances 0.000 description 36
- 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 35
- 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 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 239000000377 silicon dioxide Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 230000021615 conjugation Effects 0.000 description 27
- 239000012071 phase Substances 0.000 description 27
- 238000004440 column chromatography Methods 0.000 description 26
- 239000012043 crude product Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 24
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 20
- 230000005526 G1 to G0 transition Effects 0.000 description 19
- 238000001704 evaporation Methods 0.000 description 19
- 150000002503 iridium Chemical class 0.000 description 19
- 230000008020 evaporation Effects 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 13
- 229940126086 compound 21 Drugs 0.000 description 13
- 239000002243 precursor Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 12
- 239000011368 organic material Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 11
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 10
- 150000005360 2-phenylpyridines Chemical class 0.000 description 10
- 125000001054 5 membered carbocyclic group Chemical group 0.000 description 10
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 10
- 239000000539 dimer Substances 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 230000032258 transport Effects 0.000 description 9
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 9
- 235000019798 tripotassium phosphate Nutrition 0.000 description 9
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 8
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 8
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- MXZNUGFCDVAXLG-CHWSQXEVSA-N [(2S)-1-[(2R)-3-methyl-2-(pyridine-4-carbonylamino)butanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@@H](NC(=O)c1ccncc1)C(=O)N1CCC[C@@H]1B(O)O MXZNUGFCDVAXLG-CHWSQXEVSA-N 0.000 description 8
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 8
- 230000005587 bubbling Effects 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 8
- 229940126208 compound 22 Drugs 0.000 description 8
- 229940125846 compound 25 Drugs 0.000 description 8
- 229940125807 compound 37 Drugs 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 7
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 7
- 230000009286 beneficial effect Effects 0.000 description 7
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 7
- 229940125833 compound 23 Drugs 0.000 description 7
- 229940127204 compound 29 Drugs 0.000 description 7
- 229940125877 compound 31 Drugs 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 6
- 229910021607 Silver chloride Inorganic materials 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 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 6
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 6
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- MOSQXYPUMBJMRR-UHFFFAOYSA-N 2,5-diphenylpyridine Chemical compound C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)N=C1 MOSQXYPUMBJMRR-UHFFFAOYSA-N 0.000 description 5
- UEYFAFSFPBEVAY-UHFFFAOYSA-N 4-ethyl-2,5-diphenylpyridine Chemical compound CCC1=CC(C=2C=CC=CC=2)=NC=C1C1=CC=CC=C1 UEYFAFSFPBEVAY-UHFFFAOYSA-N 0.000 description 5
- YHQCNNMCDMYPIA-UHFFFAOYSA-N 4-methyl-2,5-diphenylpyridine Chemical compound CC1=CC(C=2C=CC=CC=2)=NC=C1C1=CC=CC=C1 YHQCNNMCDMYPIA-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 4
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- LWTGLOACRRKHMD-UHFFFAOYSA-N 4-(3-methylphenyl)-2-phenylpyridine Chemical compound CC1=CC=CC(C=2C=C(N=CC=2)C=2C=CC=CC=2)=C1 LWTGLOACRRKHMD-UHFFFAOYSA-N 0.000 description 1
- SJWHILBZPGQBJE-UHFFFAOYSA-N 4-ethylpyridin-2-amine Chemical compound CCC1=CC=NC(N)=C1 SJWHILBZPGQBJE-UHFFFAOYSA-N 0.000 description 1
- DVNVWJFDRQEWQC-UHFFFAOYSA-N 5-(3-methylphenyl)-2-phenylpyridine Chemical compound CC1=CC=CC(C=2C=NC(=CC=2)C=2C=CC=CC=2)=C1 DVNVWJFDRQEWQC-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- DSJRNLHTWHEUGX-UHFFFAOYSA-N [Ir+3].c1ccc(cc1)-c1cccc(c1)-c1ccccn1.c1ccc(cc1)-c1cccc(c1)-c1ccccn1.c1ccc(cc1)-c1cccc(c1)-c1ccccn1 Chemical compound [Ir+3].c1ccc(cc1)-c1cccc(c1)-c1ccccn1.c1ccc(cc1)-c1cccc(c1)-c1ccccn1.c1ccc(cc1)-c1cccc(c1)-c1ccccn1 DSJRNLHTWHEUGX-UHFFFAOYSA-N 0.000 description 1
- KTQKYJRYMDFFPP-UHFFFAOYSA-N [K].[K].[K].[P] Chemical compound [K].[K].[K].[P] KTQKYJRYMDFFPP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002471 indium Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HXDQZKLBKPLNHT-UHFFFAOYSA-N iridium 2-(3-phenylphenyl)pyridine Chemical compound [Ir].C1(=CC(=CC=C1)C1=NC=CC=C1)C1=CC=CC=C1.C1(=CC(=CC=C1)C1=NC=CC=C1)C1=CC=CC=C1.C1(=CC(=CC=C1)C1=NC=CC=C1)C1=CC=CC=C1 HXDQZKLBKPLNHT-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
- HTFVQFACYFEXPR-UHFFFAOYSA-K iridium(3+);tribromide Chemical compound Br[Ir](Br)Br HTFVQFACYFEXPR-UHFFFAOYSA-K 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 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
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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Description
化合物23を含む特定の化合物は、この方法を用いて生成させることができる。
特に、化合物23は以下の合成方法で、すなわち、
化合物の例
いくつかのヘテロレプティックIr(III)錯体を、以下のように合成した。
以下の合成を用いて、化合物2を作製することができた。
この以下の別の合成を用いて、化合物2を作製した。
以下の別の合成を用いて、化合物2を作製した。
すべてのデバイス実施例を、高真空(<10-7トール)熱蒸発法により組み立てた。アノード電極は1200Åのインジウムスズ酸化物(ITO)である。カソードは10ÅのLiF、次の1000ÅのAlからなる。組み立てた直後にすべてのデバイスを、窒素グローブボックス中(<1ppmのH20及びO2)で、エポキシ樹脂で密封したガラスふたで封入し、水分ゲッターをそのパッケージ中に組み込んだ。
110 基板
115 アノード
120 正孔注入層
125 正孔輸送層
130 電子阻止層
135 発光層
140 正孔阻止層
145 電子輸送層
150 電子注入層
155 保護層
160 カソード
162 第1の導電層
164 第2の導電層
Claims (63)
- 次の構造:
A-Bは、環Aの窒素原子及び環Bのsp2混成原子を介して金属Mと配位している炭素環または複素環の結合対を表し、
A-Cは炭素環または複素環の結合対を表し、
Ra、Rb及びRcは、一置換、二置換、三置換または四置換を表すことができ、
Ra、Rb及びRcは独立に、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アラルキル、アリール及びヘテロアリールからなる群から選択され、
X1、X2、X3、X4、X5、X6、X7、X8及びX9は、炭素であり、
R1、R2、及びCと隣接するRa置換基のうち、1つだけがアルキルであり、他は水素であり、
ここで金属Mがイリジウムであり、
mは金属Mの酸化数であり、
nは少なくとも1であり、
L'は、
からなる群から選択される)
を有する化合物。 - Aがピリジンである、請求項1に記載の化合物。
- R1、R2及びCと隣接するRa置換基のうちの1つだけがエチルである、請求項1に記載の化合物。
- R1、R2及びCと隣接するRa置換基のうちの1つだけがメチルである、請求項1に記載の化合物。
- Cと隣接する置換基R a がアルキルである、請求項1に記載の化合物。
- Cと隣接する置換基R a がエチルである、請求項1に記載の化合物。
- Cと隣接する置換基がメチルである、請求項1に記載の化合物。
-
からなる群から選択される、請求項1に記載の化合物。 -
-
-
R5は、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アラルキル、アリール及びヘテロアリールからなる群から選択される)
からなる群から選択される、請求項1に記載の化合物。 - R1及びR2が水素であり、R3及びR4の1つがアルキルである、請求項11に記載の化合物。
-
- R1及びR2の1つがアルキルであり、R3及びR4が水素である、請求項11に記載の化合物。
-
-
からなる群から選択される、請求項1に記載の化合物。 - ホモレプティックである、請求項1に記載の化合物。
-
- ヘテロレプティックである、請求項1に記載の化合物。
-
- 前記アルキルがピリジン環上にある、請求項5に記載の化合物。
-
- 前記アルキルがピリジン環の窒素に対してパラ位にある、請求項5に記載の化合物。
-
- アノード:
カソード;及び
前記アノードとカソードの間に配置された有機層
を含む有機発光性デバイスであって、前記有機層が次式:
A-Bは、環Aの窒素原子及び環Bのsp2混成原子を介して金属Mと配位している炭素環または複素環の結合対を表し、
A-Cは炭素環または複素環の結合対を表し、
Ra、Rb及びRcは、一置換、二置換、三置換または四置換を表すことができ、
Ra、Rb及びRcは独立に、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アラルキル、アリール及びヘテロアリールからなる群から選択され、
X1、X2、X3、X4、X5、X6、X7、X8及びX9は、炭素であり、
R1、R2、及びCと隣接するRa置換基のうち、1つだけがアルキルであり、他は水素であり、
ここで金属Mがイリジウムであり、
mは金属Mの酸化数であり、
nは少なくとも1であり、
L'は、
からなる群から選択される)
を有する化合物をさらに含むデバイス。 - Aがピリジンである、請求項25に記載のデバイス。
- Cと隣接するR a 置換基がアルキルである、請求項25に記載のデバイス。
- 前記化合物が、
R5は、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アラルキル、アリール及びヘテロアリールからなる群から選択される)
からなる群から選択される、請求項25に記載のデバイス。 - 前記化合物が、
からなる群から選択される、請求項28に記載のデバイス。 - 前記化合物が、
- 前記化合物が、
- 前記有機層が発光層であり、式IIの式を有する化合物が発光性ドーパントである、請求項25に記載のデバイス。
- 前記有機層がホストをさらに含む、請求項32に記載のデバイス。
- 前記ホストが次の構造:
を有する、請求項33に記載のデバイス。 - アノード:
カソード;及び
前記アノードとカソードの間に配置された有機層
をさらに含むデバイスを含む消費者製品であって、前記有機層が次式:
A-Bは、環Aの窒素原子及び環Bのsp2混成原子を介して金属Mと配位している炭素環または複素環の結合対を表し、
A-Cは炭素環または複素環の結合対を表し、
Ra、Rb及びRcは、一置換、二置換、三置換または四置換を表すことができ、
Ra、Rb及びRcは独立に、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アラルキル、アリール及びヘテロアリールからなる群から選択され、
X1、X2、X3、X4、X5、X6、X7、X8及びX9は、炭素であり、
R1、R2、及びCと隣接するRa置換基のうち、1つだけがアルキルであり、他は水素であり、
ここで金属Mがイリジウムであり、
mは金属Mの酸化数であり、
nは少なくとも1であり、
L'は、
からなる群から選択される)
を有する化合物をさらに含む消費者製品。 - ホモレプティックIr(III)錯体を作製するための方法であって、
Sは中性配位子であり、
Xは対イオンであり、
Aは、6員の芳香族複素環であり、Bは、6員の芳香族炭素環であり、
A-Bは、環A上の窒素原子及び環B上のsp2混成炭素原子を介してイリジウムと配位している炭素環または複素環の結合対を表し、
RA及びRBのそれぞれは、一置換、二置換、三置換または四置換を表すことができ、
RA及びRBはそれぞれ独立に、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アラルキル、アリール及びヘテロアリールからなる群から選択され、
Aが、
A-Cは炭素環または複素環の結合対を表し、
Ra及びRcは、一置換、二置換、三置換または四置換を表すことができ、
Ra及びRcは独立に、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アラルキル、アリール及びヘテロアリールからなる群から選択され、
X1、X2、X3、X4、X5、X6、X7、及びX 8 は、炭素であり、
R1、R2、及びCと隣接するRa置換基のうち、1つだけがアルキルであり、他は水素である)で表される)
を生成する段階を含む方法。 - 前記低沸点アルコールが、メタノール、エタノール、n-プロパノール、イソプロパノール、n-ブタノール、1:1の比のエタノール及びメタノール、2-メトキシエタノールならびに2-エトキシエタノールからなる群から選択される、請求項36に記載の方法。
- 前記低沸点アルコールが、エタノール、イソプロパノールならびに1:1の比のエタノール及びメタノールからなる群から選択される、請求項37に記載の方法。
- 前記低沸点アルコールが1:1の比のエタノール及びメタノールである、請求項37に記載の方法。
- Xがトリフラートである、請求項36に記載の方法。
-
-
- ホモレプティックIr(III)錯体を作製するための方法であって、
Sは中性配位子であり、
Xは対イオンであり、
Aは、6員の芳香族複素環であり、Bは、6員の芳香族炭素環であり、
A-Bは、環A上の窒素原子及び環B上のsp2混成炭素原子を介してイリジウムと配位している炭素環または複素環の結合対を表し、
RA及びRBのそれぞれは、一置換、二置換、三置換または四置換を表すことができ、
RA及びRBはそれぞれ独立に、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アラルキル、アリール及びヘテロアリールからなる群から選択され、
Aが、
A-Cは炭素環または複素環の結合対を表し、
Ra及びRcは、一置換、二置換、三置換または四置換を表すことができ、
Ra及びRcは独立に、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アラルキル、アリール及びヘテロアリールからなる群から選択され、
X1、X2、X3、X4、X5、X6、X7、及びX 8 は、炭素であり、
R1、R2、及びCと隣接するRa置換基のうち、1つだけがアルキルであり、他は水素である)で表される)
を生成する段階を含む方法。 - Xがトリフラートである、請求項43に記載の方法。
-
-
-
- 前記化合物が、
- 前記化合物が、
- アノード;
カソード;及び
前記アノードとカソードの間に配置された有機層
を含む有機発光性デバイスであって、前記有機層が、
- 前記有機層がホストをさらに含む、請求項50に記載のデバイス。
- 前記ホストがトリフェニレン基を含む、請求項51に記載のデバイス。
- 前記ホストが次式
を有する、請求項52に記載のデバイス。 - Rがテルフェニルである、請求項53に記載のデバイス。
- 前記ホストが、
- Rがジベンゾチオフェンである、請求項53に記載のデバイス。
- 前記ホストが、
- アノード;
カソード;及び
前記アノードとカソードの間に配置された有機層
をさらに含むデバイスを含む消費者製品であって、前記有機層が、
-
Xは対イオンであり、
A-Bは、環A上の窒素原子及び環B上のsp2混成炭素原子を介してイリジウムと配位している芳香族または芳香族複素環の結合対を表し、
C-Dは、環C上の窒素環原子及び環D上のsp2混成炭素原子を介してイリジウムと配位している芳香族または芳香族複素環の結合対を表し、
Aは、6員の芳香族複素環であり、Bは、6員の芳香族炭素環であり、Cは、6員の芳香族複素環であり、Dは、6員の芳香族炭素環であり、
RA、RB、RC及びRDはそれぞれ独立に、置換なし、アルキル、ヘテロアルキル、アリールまたはヘテロアリール基からなる群から選択され、
RA、RB、RC及びRDのそれぞれは、1つまたは複数の置換基を表し、
RZはアルキルであり、
Cが、
C-C’は炭素環または複素環の結合対を表し、
Ra及びRcは、一置換、二置換、三置換または四置換を表すことができ、
Ra及びRcは独立に、水素、アルキル、アルコキシ、アミノ、アルケニル、アルキニル、アラルキル、アリール及びヘテロアリールからなる群から選択され、
X1、X2、X3、X4、X5、X6、X7、及びX 8 は、炭素であり、
R1、R2、及びC’と隣接するRa置換基のうち、1つだけがアルキルであり、他は水素である)で表される)
を生成する段階を含むヘテロレプティック化合物を作製するための方法。 - Xが、トリフラート、トシレート、トリフルオロボレート及びヘキサフルオロホスフェートからなる群から選択される、請求項59に記載の方法。
- RZがメチルである、請求項59に記載の方法。
-
-
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