JP2012521436A - ヘテロレプティックイリジウム錯体 - Google Patents
ヘテロレプティックイリジウム錯体 Download PDFInfo
- Publication number
- JP2012521436A JP2012521436A JP2012502143A JP2012502143A JP2012521436A JP 2012521436 A JP2012521436 A JP 2012521436A JP 2012502143 A JP2012502143 A JP 2012502143A JP 2012502143 A JP2012502143 A JP 2012502143A JP 2012521436 A JP2012521436 A JP 2012521436A
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- Japan
- Prior art keywords
- compound
- group
- hydrogen
- compounds
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229910052741 iridium Inorganic materials 0.000 title claims description 14
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 166
- 239000002019 doping agent Substances 0.000 claims abstract description 14
- 239000010410 layer Substances 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 239000012044 organic layer Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 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 3
- 125000005580 triphenylene group Chemical group 0.000 claims description 3
- 239000003446 ligand Substances 0.000 abstract description 51
- 150000002503 iridium Chemical class 0.000 abstract description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 0 Cc(cc1)cc(-c2c3[o]c4ccccc4c3ccc22)*1I212(*(cccc3)c3-c3ccccc13)*(cccc1)c1-c1c2cccc1 Chemical compound Cc(cc1)cc(-c2c3[o]c4ccccc4c3ccc22)*1I212(*(cccc3)c3-c3ccccc13)*(cccc1)c1-c1c2cccc1 0.000 description 44
- 239000000463 material Substances 0.000 description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 238000000859 sublimation Methods 0.000 description 15
- 230000008022 sublimation Effects 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- -1 dibenzoborol Chemical compound 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 10
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 238000004770 highest occupied molecular orbital Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 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 6
- 239000011368 organic material Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 150000003222 pyridines Chemical class 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000032258 transport Effects 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 5
- NLVDIPIEDWNILG-UHFFFAOYSA-N 2-dibenzofuran-4-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CC2=C1OC1=CC=CC=C12 NLVDIPIEDWNILG-UHFFFAOYSA-N 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 230000009878 intermolecular interaction Effects 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000008901 benefit Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940127204 compound 29 Drugs 0.000 description 3
- 229940125807 compound 37 Drugs 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- 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
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 2
- FZZUHSXAUBXGKZ-UHFFFAOYSA-N 2-dibenzofuran-4-yl-4-methylpyridine Chemical compound CC1=CC=NC(C=2C=3OC4=CC=CC=C4C=3C=CC=2)=C1 FZZUHSXAUBXGKZ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 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 2
- 238000007872 degassing Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- FHTXFAHIYPAZDR-UHFFFAOYSA-N 2-bromo-9-(2-methylpropyl)carbazole Chemical compound C1=C(Br)C=C2N(CC(C)C)C3=CC=CC=C3C2=C1 FHTXFAHIYPAZDR-UHFFFAOYSA-N 0.000 description 1
- MZVSTDHRRYQFGI-UHFFFAOYSA-N 2-chloro-4-methylpyridine Chemical compound CC1=CC=NC(Cl)=C1 MZVSTDHRRYQFGI-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- PDLPSWARWUEMNL-UHFFFAOYSA-N 2-dibenzofuran-3-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=C2C3=CC=CC=C3OC2=C1 PDLPSWARWUEMNL-UHFFFAOYSA-N 0.000 description 1
- AZFABGHLDGJASW-UHFFFAOYSA-N 3-bromodibenzofuran Chemical compound C1=CC=C2C3=CC=C(Br)C=C3OC2=C1 AZFABGHLDGJASW-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
- COGPAINOKUIHFG-UHFFFAOYSA-N 9-(2-methylpropyl)-2-pyridin-2-ylcarbazole Chemical compound C1=C2N(CC(C)C)C3=CC=CC=C3C2=CC=C1C1=CC=CC=N1 COGPAINOKUIHFG-UHFFFAOYSA-N 0.000 description 1
- FNSKAYCNYRWNES-UHFFFAOYSA-N C(C1C=C2)C1c1c2c2cccc(-c3cccc(-c4ccc(c(cccc5)c5c5ccccc55)c5c4)c3)c2[s]1 Chemical compound C(C1C=C2)C1c1c2c2cccc(-c3cccc(-c4ccc(c(cccc5)c5c5ccccc55)c5c4)c3)c2[s]1 FNSKAYCNYRWNES-UHFFFAOYSA-N 0.000 description 1
- RMLKLSCEWKVMBA-UHFFFAOYSA-N C1=CC=CC=2OC3=C(C21)C=CC=C3.[N+](=O)([O-])C=3C=CC2=C(OC1=C2C=CC=C1)C3 Chemical compound C1=CC=CC=2OC3=C(C21)C=CC=C3.[N+](=O)([O-])C=3C=CC2=C(OC1=C2C=CC=C1)C3 RMLKLSCEWKVMBA-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- FFYZMBQLAYDJIG-UHFFFAOYSA-N dibenzofuran-2-amine Chemical compound C1=CC=C2C3=CC(N)=CC=C3OC2=C1 FFYZMBQLAYDJIG-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
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- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002504 iridium compounds Chemical class 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000002950 monocyclic group Chemical group 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
- 239000003921 oil Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
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- 150000003852 triazoles Chemical class 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本出願は、2009年3月23日に出願した米国仮出願No.61/162,470号、及び2010年3月19日に出願した米国出願No.12/727,615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。
本発明は、有機発光デバイスに有利に用いることができる新規な有機錯体に関する。より詳細には、本発明は、ピリジルベンゾ置換配位子を含む新規なヘテロレプティックイリジウム錯体、及びそれらの化合物を含むデバイスに関する。
Xは、NR、O、S、BR、及びSeからなる群から選択される。Rは水素及びアルキルから選択される。Rは4又はそれより少ない炭素原子を有することが好ましい。R1、R2、R3、及びR4は、モノ、ジ、トリ、又はテトラ置換を表すことができる。R1、R2、R3、及びR4のそれぞれは独立に、水素、アルキル、及びアリールからなる群から選択される。式IのR1、R2、R3、及び/又はR4の位置のアルキル基は、4又はそれより少ない炭素原子(例えば、メチル、エチル、プロピル、ブチル、及びイソブチル)を有することが好ましい。好ましくはR1及びR4は独立に、水素又は4以下の炭素原子を有するアルキル基であり、より好ましくはR1及びR4は独立に、水素又はメチルである。好ましくは、R2及びR3は独立に、水素又は4以下の炭素原子を有するアルキルであり、より好ましくはR2及びR3は独立に、水素又はメチルであり、最も好ましくはR2及びR3は水素である。
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。
ピリジルジベンゾチオフェン配位子を含むこれらの化合物は、良好な特性を示すデバイスに用いることもできる。例えば、XがSである化合物は、向上した安定性及び生産性を有するデバイスをもたらしうる。
4-ジベンゾフランボロン酸(5.0 g, 23.6 mmol)、2-クロロピリジン(2.2 g, 20 mmol)、ジシクロへキシル(2’,6’-ジメトキシビフェニル-2-イル)ホスフィン(S-Phos)(0.36 g, 0.8 mmol)、及びリン酸カリウム(11.4 g, 50 mmol)を、100 mLのトルエンと10 mLの水の中で混ぜた。窒素をその混合物中へ30分間直接バブリングさせた。次に、Pd2(dba)3(0.18 g, 0.2 mmol)を添加し、混合物を窒素下で8時間加熱し還流させた。その混合物を冷却し、有機層を分離した。有機層を食塩水で洗い、硫酸マグネシウム上で乾燥させ、濾過し、溶媒留去して残留物を得た。この残留物を、ジクロロメタ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。4.5 gの所望の生成物が精製後に得られた。
イリジウムトリフラート前駆体(0.97 g, 1.4 mmol)と2-(ジベンゾ[b,d]フラン-4-イル)ピリジン(1.0 g, 4.08 mmol)を50 mLのエタノール中で混ぜた。この混合物を24時間、窒素下で加熱還流させた。還流中に沈殿物が生じた。反応混合物をセライト床を通した濾過した。生成物をメタノール及びヘキサンで洗った。その固体をジクロロメタンに溶かし、1:1のジクロロメタン及びヘキサンを用いるカラムによって精製した。0.9 gの純粋な生成物がカラム精製後に得られた(HPLC純度: 99.9%)。
250 mLの丸底フラスコ中の80 mLのトリフルオロ酢酸にジベンゾフラン(7.06 g, 42 mmol)を添加し、激しく撹拌してその内容物を室温で溶かした。この溶液をつぎに氷上で冷やし、20 mLのトリフルオロ酢酸中の1.2当量の70% HNO3(4.54 g, 50.40 mmol)を、撹拌している溶液中にゆっくり注ぎ入れた。30分間撹拌した後、フラスコから内容物を150 mLの氷水に注ぎ入れ、さらに15分間撹拌した。灰白色の沈殿物を次に濾過し、最後に2M NaOH及び水で洗った。湿った物質を次に1.5 Lの沸騰メタノールから、淡黄色結晶の形態に再結晶した。7.2 gの生成物を単離した。
3-ニトロジベンゾフラン(6.2 g, 29.08 mmol)を360 mLの酢酸エチルに溶かし、その溶液に窒素ガスを通すことによって5分間脱気した。500 mgのPd/Cをその溶液に添加し、内容物を60 psiの圧力で水素化した。反応は、水素化容器内の圧力が15分間60psiで安定するまで行った。反応物を次に小さなセライトパッドを通して濾過し、灰白色の生成物を得た(5.3 g, 28.9 mmol)。
0℃に保ったコニカルフラスコ中の20 mLのconc. H2SO4に、NaNO2(2.21 g, 32.05 mmol)を溶かした。次に、最少量の氷酢酸中の2-アミノジベンゾフラン(5.3 g, 28.9 mmol)の溶液を、温度が決して5〜8℃より高くならないように、そのフラスコにゆっくり添加し、混合物を0℃でさらに1.5時間撹拌した。その撹拌した混合物に100 mLのエーテルを添加し、相当するジアゾ塩の沈殿が直ちに沈んだ。茶色のジアゾ塩を直ぐに濾過し、150 mLの48%HBr中にCuBr(6.25 g, 43.5 mmol)を含むフラスコに移した。このフラスコを次に64℃に保った水浴に入れ、2時間撹拌した。室温まで冷やした後、濃い色の反応内容物を濾過し、沈殿物を水で2回洗った。単離した固体を次に5〜10%DCM/ヘキサンを用いてシリカゲルカラム上でフラッシュクロマトして4.79 gの最終化合物を得た。
3-ブロモジベンゾフラン(4.79 g, 19.39 mmol)、ビスピナコラートジボロン(6.4 g, 25.2 mmol)、KOAc(7.61 g, 77.54 mmol)を丸底フラスコ中、100 mLのジオキサンに添加した。内容物を30分間、窒素ガスのバブリング下で脱ガスし、Pd(dppf)2Cl2(158 mg, 0.019 mmol)をその反応混合物に添加した。さらに10分間脱ガスした後、反応混合物を80℃に加熱し、夜通し撹拌した。次に反応フラスコを室温まで冷やし、セライトパッドを通して濾過した。つぎに、濃茶色の溶液を食塩水と酢酸エチルとの間で分配させた。有機層を集め、無水Na2SO4上で乾燥させ、過剰な溶媒を減圧下で蒸発させた。次に、茶色の固体をシリカゲルカラムにドライチャージし、5%酢酸エチル/ヘキサン/0.005%トリエチルアミンを用いて速やかにフラッシュクロマトにかけ、5.08 gの最終生成物を得た。
ジベンゾフランボロネートエステル(5.85 g, 20 mmol)、2-ブロモピリジン(2.93 mL, 30 mmol)、30 mLの2 M Na2CO3(60 mmol)を500 mLの三ツ口丸底フラスコ中で200 mLのトルエン/エタノール(1:1)中でスラリーにし、窒素ガスのバブリング下で30分間脱ガスした。Pd(dppf)2Cl2(160 mg, 0.2 mmol)をそのスラリーに添加し、脱ガスをさらに10分間続けた。次に反応内容物を夜通し還流させた。反応内容物を室温に冷やし、小さなセライトパッドを通して濾過した。次に、茶色の二相溶液を食塩水と酢酸エチルの間で分配させた。有機層を無水Na2SO4上で乾燥させ、過剰な溶媒を減圧下で蒸発させた。前の工程からの残留物をシリカゲルカラムにドライチャージし、5〜8%酢酸エチル/ヘキサンで溶出させて、4.3 gの最終生成物を得た。
イリジウムトリフラート前駆体(2.8 g, 3.9 mmol)、2-(ジベンゾフラン-3-イル)ピリジン(4 g, 16.3 mmol)を100 mLのエタノール中で夜通し還流させた。明るい黄色の沈殿物を濾過し、乾燥させ、シリカゲルカラムにドライチャージした。210 mgの最終化合物を、3:2 DCM/ヘキサンを用いての溶出後に単離した。
イリジウムトリフラート前駆体(1.6 g, 2.2 mmol)及び2-(ジベンゾ[b,d]フラン-4-イル)ピリジン(1.6 g, 6.5 mmol)を50 mLのエタノールに混ぜた。この混合物を24時間、窒素下で加熱還流させた。還流中に沈殿物が生じた。反応混合物をセライト床を通して濾過した。生成物をメタノール及びヘキサンで洗った。その固体をジクロロメタンに溶かし、1:1のジクロロメタン及びヘキサンを用いるカラムによって精製した。1.4 gの純粋な生成物が、カラム精製後に得られた。
4-ジベンゾフランボロン酸(5.0 g, 23. 6 mmol)、2-クロロ-4-メチルピリジン(2.6 g, 20 mmol)、ジシクロへキシル(2’,6’-ジメトキシビフェニル-2-イル)ホスフィン(S-Phos)(0.36 g, 0.8 mmol)、及びリン酸カリウム(11.4 g, 50 mmol)を100 mLのトルエン及び10 mLの水に混ぜた。窒素を30分間その混合物中へ直接バブリングさせた。次に、Pd2(dba)3を添加し(0.18 g, 0.2 mmol)、その混合物を8時間窒素下で加熱還流させた。その混合物を冷やし、有機層を分離した。その有機層を食塩水で洗い、硫酸マグネシウム上で乾燥させ、濾過し、残留物になるまで溶媒留去した。その残留物を、ジクロロメタ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た。4.7 gの所望の生成物が精製後に得られた。
イリジウムトリフラート前駆体(2.0 g, 2.7 mmol)及び4-メチル-2-(ジベンゾ[b,d]フラン-4-イル)ピリジン(2.1 g, 8.1 mmol)を60 mLのエタノールに混ぜた。この混合物を24時間窒素下で加熱還流させた。還流中に沈殿物が生じた。反応混合物をセライト床を通して濾過した。生成物をメタノール及びヘキサンで洗った。その固体をジクロロメタンに溶かし、1:1のジクロロメタン及びヘキサンを用いるカラムによって精製した。1.6 gの純粋な生成物がカラム精製後に得られた。
o-ヨードニトロベンゼン(9.42 g, 37.84 mmol)、4-ブロモベンゼンボロン酸(7.6 g, 37.84 mmol)、炭酸カリウム(21 g, 151.36 mmol)を190 mLのDME/水(3:2)溶液に添加し、30分間脱ガスした。Pd(PPh3)4(437 mg, 0.38 mmol)を窒素下でそのスラリーに添加し、そのスラリーをさらに5分間脱ガスした。反応物を窒素下で6時間還流させた。フラスコの内容物をセライトのパッドを通して濾過し、酢酸エチルと食塩水に分配させた。有機層を無水Na2SO4上で乾燥させ、減圧下で溶媒蒸発させた。粗生成物黄色オイルを5%酢酸エチル/ヘキサンを用いるシリカゲルの上でフラッシュクロマトした。最終化合物は無色オイルとして単離された(9.8 g, 35.4 mmol)。
4’-ブロモ-2-ニトロビフェニル(9.8 g, 35.4 mmol)を30 mLのトリエチルホスファイトとともに夜通し還流させた。その溶液を室温まで冷やした後、40 mLの6(N) HClをそこへゆっくり添加し、80℃に3時間加熱した。酸性溶液をconc. NaOHで途中まで中和し、その酸性溶液の残りを固体のNa2CO3で中和した。曇った溶液を酢酸エチル(500 mL)で3回抽出した。一緒にした有機層を減圧下で溶媒蒸発させ、粗生成物をシリカゲル上でフラッシュクロマトした(15%〜30%酢酸エチル/ヘキサン)。4.1 gの最終化合物を灰白色固体として単離した。
2-ブロモ-9H-カルバゾール(4.1 g, 16.74 mmol)をDMFに溶かした。撹拌した溶液にNaH(1.8 g, 75.5 mmol)を3回に分けて添加した。撹拌したスラリーにイソブチルブロマイド(4.8 mL, 43.2 mmol)を添加し、20分間待った後、60℃に4時間温めた。反応混合物を室温まで冷やし、飽和NH4Cl溶液の滴下による添加によって注意深く反応を停止させた。内容物を次に食塩水及び酢酸エチルに分配した。有機層を無水Na2SO4の上で乾燥させ、減圧下で溶媒を蒸発させた。粗生成物を、10%酢酸エチル/ヘキサンを用いてシリカゲル上でフラッシュクロマトにかけた。最終生成物(4.45 g, 14.8 mmol)を白色固体として単離した。
2-ブロモ-9-イソブチル-9H-カルバゾール(4.45 g, 14.78 mmol)、ビスボロンピナコラート(4.7 g, 18.5 mmol)、酢酸カリウム(5.8 g, 59.1 mmol)を75 mLの無水トルエンに入れ、30分間脱ガスした。そのスラリーに窒素下でPd2dba3(362 mg, 0.443 mmol)を添加し、スラリーをさらに5分間脱ガスした。夜通し撹拌した後、反応の内容物を冷やし、セライトパッドを通して濾過した。トルエン溶液を水と酢酸エチルで分配させた。有機層を無水Na2SO4の上で乾燥させ、溶媒を減圧下で蒸発させた。固体粗生成物を10%酢酸エチル/ヘキサンを用いるシリカゲルでフラッシュクロマトした。単離した固体を133℃でクーゲルロール蒸留にかけて残留ビスボロンピナコラートを除去した。最終生成物(4.77 g, 13.7 mmol)を灰白色固体として単離した。
9-イソブチル-2-ピナコールボロン-9H-カルバゾール(1.45 g, 4 mmol)、2-ブロモピリジン(760 mg, 4.8 mmol)、2-ジシクロへキシルホスフィノ-2’,6’-ジメトキシビフェニル(67 mg, 0.16 mmol)、K3PO4・H2O(3.68 g, 16 mmol)を9:1のトルエン及び水の混合物40 mLに添加した。内容物を30分間脱ガスし、次にPd2dba3(37 mg, 0.04 mmol)を添加し、さらに5分間脱ガスした。夜通し還流した後、反応内容物を室温まで冷やし、セライトパッドを通して濾過した。濾液を水及び酢酸エチルに分配した。有機層を単離し、無水Na2SO4上で乾燥させ、減圧下で溶媒留去した。粗生成物を次に10%〜30%酢酸エチル/ヘキサンを用いてシリカゲル上でフラッシュクロマトして脱ボラン化前の生成物を除去した。最終化合物(620 mg, 2.1 mmol)を白色固体として単離した。
前の段階からのカルバゾール配位子(620 mg, 2.1 mmol)をエタノールに溶かし、そこに中間体-1を窒素下で添加した。次に溶液を夜通し還流させた。濃橙色の沈殿物を濾過し、50%DCM/ヘキサンを用いてシリカゲル上でフラッシュクロマトした。単離した生成物を次に昇華させて310 mgの99.7%純度の生成物を得た。
イリジウムトリフラート前駆体(2.0 g, 2.7 mmol)及び4-メチル-2-(ジベンゾ[b,d]フラン-4-イル)ピリジン(2.1 g, 8.1 mmol)を60 mLのエタノールに混ぜた。混合物を24時間窒素下で加熱還流させた。沈殿物が還流中に生じた。反応混合物をセライト床を通して濾過した。生成物をメタノール及びヘキサンで洗った。その固体をジクロロメタンに溶かし、1:1のジクロロメタン及びヘキサンを用いるカラムによって精製した。1.0gの純粋な生成物がカラム精製後に得られた。
2-(ジベンゾ[b,d]フラン-4-イル)ピリジン(5.0 g, 20.39 mmol)及びイリジウムトリフラート(5.0 g, 5.59 mmol)を100 mLのエタノール及びメタノールの1:1溶液とともに250 mLの丸底フラスコに入れた。この反応混合物を24時間還流させた。明るい黄色の沈殿物が得られた。反応物を室温まで冷やし、エタノールで希釈した。セライトを添加し、反応混合物をシリカゲル栓を通して濾過した。その栓をエタノール(2×50 mL)、次いでヘキサン(2×50 mL)で洗った。シリカゲル栓上に残った生成物を、きれいな受け用フラスコ中にジクロロメタンで溶出させた。ジクロロメタンを減圧下で除去し、生成物をジクロロメタンとイソプロパノールの混合物から再結晶させた。その黄色固体を濾過し、メタノール次いでヘキサンで洗って、明るい黄色結晶生成物を得た。この生成物をトルエンからの再結晶、次にアセトニトリルからの再結晶によってさらに精製して、HPLCによる純度が99.5%の生成物1.94 g(37.5%収率)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800Å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 (36)
- R1及びR4が独立に、水素及び4つ以下の炭素原子を有するアルキルからなる群から選択される、請求項1記載の化合物。
- R1及びR4が独立に、水素及びメチルからなる群から選択される、請求項1記載の化合物。
- R2及びR3が独立に、水素、4つ以下の炭素原子を有するアルキル、及びその環内に6つ以下の原子をもつアリールからなる群から選択される、請求項1記載の化合物。
- R2及びR3が独立に、水素、メチル、及びフェニルからなる群から選択される、請求項1記載の化合物。
- R2及びR3が水素である、請求項1記載の化合物。
- R1、R2、R3、及びR4が独立に、水素、4つ以下の炭素原子を有するアルキル、及びその環内に6つ以下の原子をもつアリールからなる群から選択される、請求項1記載の化合物。
- R1、R2、R3、及びR4が独立に、水素、メチル、及びフェニルからなる群から選択される、請求項1記載の化合物。
- R1、R2、R3、及びR4が水素である、請求項1に記載の化合物。
- Rが4つ以下の炭素原子を有する、請求項1に記載の化合物。
- XがOである、請求項1に記載の化合物。
- XがSである、請求項1に記載の化合物。
- XがNRである、請求項1に記載の化合物。
- 前記第一のデバイスが消費者製品である、請求項28に記載のデバイス。
- R2及びR3が独立に、水素、4つ以下の炭素原子を有するアルキル、及びその環に6つ以下の原子をもつアリールからなる群から選択される、請求項28に記載のデバイス。
- さらに前記有機層がホストを含む、請求項28に記載のデバイス。
- 前記ホストがトリフェニレン部分及びジベンゾチオフェン部分を含む、請求項34に記載のデバイス。
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US20230309376A1 (en) | 2023-09-28 |
US11637251B2 (en) | 2023-04-25 |
EP3178831B1 (en) | 2020-04-29 |
CN112028941A (zh) | 2020-12-04 |
CN104892679A (zh) | 2015-09-09 |
CN102439019B (zh) | 2015-06-03 |
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US8722205B2 (en) | 2014-05-13 |
US20240180020A1 (en) | 2024-05-30 |
JP2015134823A (ja) | 2015-07-27 |
EP3643721A1 (en) | 2020-04-29 |
CN107880077B (zh) | 2019-08-13 |
US10056566B2 (en) | 2018-08-21 |
JP5981603B2 (ja) | 2016-08-31 |
KR101748543B1 (ko) | 2017-06-16 |
JP5744835B2 (ja) | 2015-07-08 |
KR101698220B1 (ko) | 2017-01-19 |
KR20160118381A (ko) | 2016-10-11 |
US20100244004A1 (en) | 2010-09-30 |
CN107880077A (zh) | 2018-04-06 |
TWI577673B (zh) | 2017-04-11 |
TW201038563A (en) | 2010-11-01 |
US20180323383A1 (en) | 2018-11-08 |
CN112028941B (zh) | 2023-08-29 |
KR20110130475A (ko) | 2011-12-05 |
CN102439019A (zh) | 2012-05-02 |
EP2411401A1 (en) | 2012-02-01 |
WO2010111175A1 (en) | 2010-09-30 |
EP3178831A1 (en) | 2017-06-14 |
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