TWI493015B - 發光有機金屬錯合物 - Google Patents
發光有機金屬錯合物 Download PDFInfo
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- TWI493015B TWI493015B TW097116553A TW97116553A TWI493015B TW I493015 B TWI493015 B TW I493015B TW 097116553 A TW097116553 A TW 097116553A TW 97116553 A TW97116553 A TW 97116553A TW I493015 B TWI493015 B TW I493015B
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- 125000002524 organometallic group Chemical group 0.000 title description 3
- 239000010410 layer Substances 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 101
- 239000000463 material Substances 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 239000002019 doping agent Substances 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 239000012044 organic layer Substances 0.000 claims description 34
- 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 claims description 19
- 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 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 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
- 239000000470 constituent Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 255
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 235
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 232
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 210
- 239000000047 product Substances 0.000 description 131
- 239000000203 mixture Substances 0.000 description 123
- 229910052757 nitrogen Inorganic materials 0.000 description 114
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- 235000019439 ethyl acetate Nutrition 0.000 description 93
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
- 239000011541 reaction mixture Substances 0.000 description 80
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- 238000006243 chemical reaction Methods 0.000 description 66
- 239000002904 solvent Substances 0.000 description 63
- 239000000243 solution Substances 0.000 description 53
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 47
- 238000010992 reflux Methods 0.000 description 47
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 45
- 239000000499 gel Substances 0.000 description 45
- 239000007787 solid Substances 0.000 description 44
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
- 238000004440 column chromatography Methods 0.000 description 40
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 39
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 38
- 239000003446 ligand Substances 0.000 description 35
- 229910000420 cerium oxide Inorganic materials 0.000 description 30
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 30
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 26
- 239000000284 extract Substances 0.000 description 26
- 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 26
- 238000000034 method Methods 0.000 description 26
- 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 26
- 238000001704 evaporation Methods 0.000 description 24
- 230000008020 evaporation Effects 0.000 description 24
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 24
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 22
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 21
- 235000019341 magnesium sulphate Nutrition 0.000 description 21
- 238000000746 purification Methods 0.000 description 20
- 238000001816 cooling Methods 0.000 description 19
- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
- 239000012043 crude product Substances 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 17
- 238000006467 substitution reaction Methods 0.000 description 16
- 239000000539 dimer Substances 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 15
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 14
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 14
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 11
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 10
- 101100232347 Mus musculus Il11ra1 gene Proteins 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 201000001366 familial temporal lobe epilepsy 2 Diseases 0.000 description 10
- 125000001475 halogen functional group Chemical group 0.000 description 10
- 238000002506 high-vacuum sublimation Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 10
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 9
- 229940093475 2-ethoxyethanol Drugs 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000005909 Kieselgur Substances 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- -1 bis(4-methyl-2-phenylpyridine) ruthenium (III) Chemical compound 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 229910000160 potassium phosphate Inorganic materials 0.000 description 9
- 235000011009 potassium phosphates Nutrition 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 9
- 235000019798 tripotassium phosphate Nutrition 0.000 description 9
- ZAZPDOYUCVFPOI-UHFFFAOYSA-N 2-methylpropylboronic acid Chemical compound CC(C)CB(O)O ZAZPDOYUCVFPOI-UHFFFAOYSA-N 0.000 description 8
- 125000002877 alkyl aryl group Chemical group 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 description 8
- 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 8
- 230000000694 effects Effects 0.000 description 8
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 8
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000003107 substituted aryl group Chemical group 0.000 description 8
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 7
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 7
- 229960004448 pentamidine Drugs 0.000 description 7
- 235000011056 potassium acetate Nutrition 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- WLPFTJXVEBANAM-UHFFFAOYSA-N 2-(3-bromophenyl)pyridine Chemical compound BrC1=CC=CC(C=2N=CC=CC=2)=C1 WLPFTJXVEBANAM-UHFFFAOYSA-N 0.000 description 6
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- 208000030060 Congenital non-bullous ichthyosiform erythroderma Diseases 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000004576 sand Substances 0.000 description 6
- 230000032258 transport Effects 0.000 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 description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 4
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 4
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 4
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 229940126657 Compound 17 Drugs 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000012327 Ruthenium complex Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 4
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940125878 compound 36 Drugs 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- AFSSVCNPDKKSRR-UHFFFAOYSA-N (3-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Br)=C1 AFSSVCNPDKKSRR-UHFFFAOYSA-N 0.000 description 3
- BJQCPCFFYBKRLM-UHFFFAOYSA-N (3-methylphenyl)boronic acid Chemical compound CC1=CC=CC(B(O)O)=C1 BJQCPCFFYBKRLM-UHFFFAOYSA-N 0.000 description 3
- TYGDOTIDCKHYET-UHFFFAOYSA-N 2-(3,5-dimethylphenyl)pyridine Chemical compound CC1=CC(C)=CC(C=2N=CC=CC=2)=C1 TYGDOTIDCKHYET-UHFFFAOYSA-N 0.000 description 3
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 3
- BZUUVQCSPHPUQA-UHFFFAOYSA-N 2-bromo-5-chloropyridine Chemical compound ClC1=CC=C(Br)N=C1 BZUUVQCSPHPUQA-UHFFFAOYSA-N 0.000 description 3
- 150000005360 2-phenylpyridines Chemical class 0.000 description 3
- 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 3
- 230000004888 barrier function Effects 0.000 description 3
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- VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 0.000 description 1
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- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- WYRXRHOISWEUST-UHFFFAOYSA-K ruthenium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Ru+3] WYRXRHOISWEUST-UHFFFAOYSA-K 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
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- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
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- MEKXWJWQKGDLFI-UHFFFAOYSA-L zinc;pyridine;dibromide Chemical compound [Zn+2].[Br-].[Br-].C1=CC=NC=C1 MEKXWJWQKGDLFI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- 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
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
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Description
本發明係關於有機發光裝置(OLED)。更特定而言，本發明係關於可具有經改良裝置製造、製作、穩定性、效率、及/或色彩之發光有機金屬材料及裝置。
多種原因使得使用有機材料之光電子裝置變得越來越理想。用於製造該等裝置之許多材料價格相對較低廉，因此有機光電子裝置較無機裝置具有成本優勢之潛力。此外，有機材料之固有性質(例如其撓性)使其極適用於特定應用中，例如於撓性基板上之製作。有機光電子裝置之實例包括有機發光裝置(OLED)、有機光電電晶體、有機光伏打電池及有機光檢測器。對於OLED，有機材料可具有優於習用材料之性能優勢。舉例而言，有機發射層所發射光之波長通常可容易地用適當摻雜物進行調整。
OLED使用當在裝置兩端施加電壓時發光之薄有機膜。在諸如平板顯示器、照明及背光等應用中使用OLED正變成越來越令人感興趣之技術。許多OLED材料及構造闡述於美國專利第5,844,363號、第6,303,238號及第5,707,745號中，該等專利之全文皆以引用方式併入本文中。
磷光發射分子之一種應用係全色顯示器。此顯示器之工業標準要求適於發射特定色彩(稱為"飽和"色)之像素。尤其，該等標準要求飽和紅色、綠色及藍色像素。色彩可使用CIE坐標量測，其已為該項技術習知。
綠色發射分子之一個實例係叁(2－苯基吡啶)銥(標記為Ir(ppy)3
)，其具有下式I之結構：
在此處及本文隨後圖中，將自氮至金屬(此處Ir)之配位鍵繪示成直線。
本文所用術語"有機物"包括可用於製作有機光電子裝置之聚合物材料以及小分子有機材料。"小分子"意指任何不為聚合物之有機材料，且"小分子"實際上可相當大。在一些情況下，小分子可包括重複單元。舉例而言，使用長鏈烷基作為取代基不能將分子排除在"小分子"類別外。小分子亦可納入聚合物中，例如作為聚合物骨架上之側基或作為骨架之一部分。小分子亦可用作樹枝狀聚合物之核心部分，樹枝狀聚合物由一系列化學殼層構築於核心部分上而構成。樹枝狀聚合物之核心部分可係螢光或磷光小分子發射體。樹枝狀聚合物可係"小分子"，且據信當前用於OLED領域之所有樹枝狀聚合物皆係小分子。
本文所用"頂部"意指距基板最遠的地方，而"底部"意指距基板最近的地方。當第一層闡述為"佈置於"第二層之上時，則該第一層遠離基板而佈置。除非指明該第一層與該第二層"接觸"，否則在該第一與第二層間可能有其他層。舉例而言，陰極可闡述為"佈置於"陽極之上，即使其間有各種有機層。
本文所用"溶液可處理的"意指能於液體介質中溶解、分散或傳送及/或自液體介質沈積，該液體介質呈溶液或懸浮液形式。
當相信配位基有助於發射材料之光活性性質時，則稱其具有"光活性"。
關於OLED、及上述定義之更詳細內容可在美國專利第7,279,704號中找到，其整體內容皆以引用的方式併入本文中。
本發明提供用於OLED中之材料。該等材料為具有經烷基及/或芳基取代之配位基及異配或均配性質之2－苯基吡啶銥(Irppy)錯合物。該等材料可有利地用於OLED中。
該等材料含有具有下式之異配銥化合物：
其中n＝1或2；R1
、R2
、R3
、R4
及R5
獨立選自由氫、烷基及芳基組成之群，且其中R1
、R2
、R3
、R4
及R5
中每一個皆可代表單、二、三、四或五取代；且R1
、R2
、R3
、R4
及R5
中至少一個為烷基或芳基。
在一個態樣中，該等材料含有具有下式之異配銥化合物：
其中n＝1或2；R1
、R2
、R5
及R6
獨立選自由氫、烷基及芳基組成之群；R1
、R2
、R5
及R6
中至少一個為烷基或芳基；且R3
、R4
及R7
獨立選自由氫、烷基及芳基組成之群，且其中R3
、R4
及R7
可代表單、二、三、四或五取代。
在另一態樣中，該等材料含有具有下式之異配銥化合物：
其中n＝1或2；R1
、R2
、R5
及R6
獨立選自由氫、烷基及芳基組成之群；R1
、R2
、R5
及R6
中至少一個為烷基或芳基；且R3
、R4
及R7
獨立選自由氫、烷基及芳基組成之群，且其中R3
、R4
及R7
中每一個皆可代表單、二、三、四或五取代。
在另一態樣中，該等材料含有具有下式之異配銥化合物：
其中n＝1或2；R1
及R4
獨立選自由氫、烷基及芳基組成之群；R1
及R4
中至少一個為烷基或芳基；且R2
、R3
及R5
獨立選自由氫、烷基及芳基組成之群，且其中R2
、R3
及R5
中每一個皆可代表單、二、三、四或五取代。
在另一態樣中，該等材料含有具有下式之異配銥化合物：
其中n＝1或2；R1
、R2
、R3
、R4
、R5
及R6
獨立選自由氫、烷基及芳基組成之群，且其中R1
、R2
、R3
、R4
、R5
及R6
中每一個皆可代表單、二、三、四或五取代；R1
、R2
、R3
、R4
及R5
中至少一個為烷基或芳基；且至少R1
不同於R4
，R2
不同於R5
，或R3
不同於R6
。
在另一態樣中，該等材料具有選自由以下組成之群之均配銥化合物：
在另一態樣中，該等材料具有包括選自以下群組之配位
基的化合物，其中該配位基配位至原子序數大於40之金屬。
此外，本發明提供有機發光裝置。該裝置包含陽極、陰極、及佈置於該陽極與該陰極之間之有機發射層，該有機層進一步包含發射摻雜物，其中上述化合物為該發射摻雜物。該有機發射層進一步包含主體材料。本發明提供包含特定主體材料及特定摻雜物之特定裝置。
本發明提供以經改良產率製得Ir(La
)(Lb
)(Lc
)錯合物之方法，該方法包含使具有式(La
)(Lb
)IrX之中間體與Lc
反應以產生Ir(La
)(Lb
)(Lc
)錯合物，其中La
、Lb
及Lc
係光活性且獨立地雙齒環金屬化配位基，其具有下式：
其中R3
、R4
、R5
、R6
、R'3
、R'4
、R'5
及R'6
獨立選自由以下組成之群：氫、烷基、烯基、炔基、烷基芳基、CN、CO2
R、C(O)R、NR2
、NO2
、OR、鹵基、芳基、雜芳基、經取代芳基、經取代雜芳基或雜環基團；其中R6
或R'3
中至少一個不為氫，且R6
或R'3
係選自由以下組成之群：烷基、烯基、炔基、烷基芳基、CN、CO2
R、C(O)R、NR2
、NO2
、OR、鹵基、芳基、雜芳基、經取代芳基、經取代雜芳基及雜環基團；且
通常，OLED包含至少一個佈置於陽極與陰極之間且與其電連接之有機層。當施加電流時，陽極將電洞注入有機層，且陰極將電子注入有機層。注入之電洞及電子各自向帶相反電荷之電極遷移。當電子及電洞位於同一分子上時，形成"激發子"，即具有激發能態之定域電子－電洞對。當該激發子經由光電子發射機制弛豫時，可發射光。在一些情況下，激發子可位於準分子或激態錯合物上。亦可存在非輻射機制(例如熱弛豫)，但其通常認為不理想。
初始OLED使用可自其單重態發光("螢光")之發射分子，如(例如)美國專利第4,769,292號中所揭示，該案之全文以引用的方式併入本文中。螢光發射通常在小於10奈秒之時間訊框內發生。
最近，已證實具有可自三重態發光("磷光")之發射材料的OLED。Baldo等人，"Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices"，Nature，第395卷，151－154,1998；("Baldo－I")及Baldo等人，"Very high－efficiency green organic light－emitting devices based on electrophosphorescence"，Appl.Phys.Lett，第75卷，第1期，4－6(1999)("Baldo－II")，其全文皆以引用的方式併入本文中。磷光更詳細闡述於美國專利第
7,279,704號第5－6行中，其以引用的方式併入。
自三重態發出之磷光可藉由將有機分子限制為(較佳經由鍵結)密切接近高原子序數原子來增強超過螢光。被稱為重原子效應之此現象由習知稱作自旋軌道耦合之機制產生。此磷光躍遷可自有機金屬分子(例如，叁(2－苯基吡啶)銥(III))之經激發金屬至配位基電荷轉移(MLCT)態觀測到。
圖1展示有機發光裝置100。該等圖不必按比例繪製。裝置100可包括基板110、陽極115、電洞注入層120、電洞傳送層125、電子阻擋層130、發射層135、電洞阻擋層140、電子傳送層145、電子注入層150、保護層155及陰極160。陰極160係具有第一導電層162及第二導電層164之複合陰極。裝置100可藉由按順序沈積所述層製作。該等各個層之性質及功能以及實例材料更詳細闡述於美國專利第7,279,704號第6－10行中，其以引用的方式併入。
可利用該等層每一層之更多實例。舉例而言，撓性及透明基板－陽極組合揭示於美國專利第5,844,363號中，其整體內容皆以引用的方式併入本文中。經p－摻雜之電洞傳送層之實例係經F.sub.4－TCNQ以50：1之莫耳比摻雜之m－MTDATA，如美國專利申請公開案第2003/0230980號中所揭示，該案之全文以引用的方式併入本文中。發射及主體材料之實例揭示於頒予Thompson等人之美國專利第6,303,238號中，該案之全文以引用的方式併入本文中。經n摻雜電子傳送層之實例係經Li以1：1之莫耳比摻雜之
BPhen，如美國專利申請公開案第2003/0230980號中所揭示，其整體內容皆以引用的方式併入本文中。美國專利第5,703,436號及第5,707,745號(其整體內容皆以引用的方式併入本文中)揭示多種陰極實例，其包括具有薄金屬層(例如Mg：Ag)以及上覆透明導電、濺鍍沈積之ITO層的複合陰極。阻擋層之理論及用途更詳細闡述於美國專利第6,097,147號及美國專利申請公開案第2003/0230980號中，其整體內容皆以引用的方式併入本文中。注入層之實例提供於美國專利申請公開案第2004/0174116號中，其整體內容皆以引用的方式併入本文中。保護層之闡述可在美國專利申請公開案第2004/0174116號中找到，其整體內容皆以引用的方式併入本文中。
圖2展示倒置OLED 200。該裝置包括基板210、陰極215、發射層220、電洞傳送層225及陽極230。裝置200可藉由按順序沈降所述層製作。由於最常用之OLED構造具有佈置於陽極上之陰極，而裝置200具有佈置於陽極230下之陰極215，故裝置200可稱為"倒置"OLED。與彼等針對裝置100所闡述相似之材料可用於裝置200之對應層。圖2提供一個如何自裝置100之結構省略一些層之實例。
以非限制性實例形式提供圖1及2中所示之簡單分層結構，且應瞭解，本發明之實施例可結合各種其他結構使用。所述特定材料及結構實際上具例示性，且可使用其他材料及結構。藉由以不同方式組合所述各個層可達成功能OLED，或基於設計、性能及成本因素，有多個層可完全
省略。亦可包括未具體闡述之其他層。可使用不同於彼等特定闡述材料之材料。儘管本文所提供之許多實例闡述各種層包含單一材料，但應瞭解，可使用材料之組合(例如主體材料與摻雜物之混合物)或更通常可使用混合物。此外，該等層可具有各種子層。本文中所提供用於各種層之名稱不欲具有嚴格限制意味。舉例而言，在裝置200中，電洞傳送層225傳送電洞並將電洞注入發射層220中，且其可闡述為電洞傳送層或電洞注入層。在一個實施例中，OLED可闡述為具有佈置於陰極與陽極間之"有機層"。該有機層可包含單一層，或可進一步包含(例如)參照圖1及2所述不同有機材料之多層。
亦可使用未特定闡述之結構及材料，例如由聚合材料構成之OLED(PLED)，例如闡述於頒予Friend等人之美國專利第5,247,190號中者，該案之全文以引用的方式併入本文中。進一步舉例而言，可使用具有單一有機層之OLED。OLED可經堆疊，例如在頒予Forrest等人之美國專利第5,707,745號中所述者，該案之全文以引用的方式併入本文中。OLED結構可與圖1及2中所示之簡單分層結構有偏差。舉例而言，基板可包括成角度的反射表面，以改良輸出耦合，例如頒予Forrest等人之美國專利第6,091,195號中所述之臺面結構及/或頒予Bulovic等人之美國專利第5,834,893號中所述之凹坑結構，該等專利之全文皆以引用的方式併入本文中。
除非另有說明，否則各實施例之任何層皆可藉由任何適
宜方法沈積。對於有機層而言，較佳方法包括熱蒸發、噴墨(例如在美國專利第6,013,982號及第6,087,196號中所述者，該等專利之全文以引用的方式併入本文中)、有機氣相沈積(OVPD)(例如頒予Forrest等人之美國專利第6,337,102號中所述者，該案之全文以引用的方式併入本文中)及藉由有機物蒸氣噴射印刷(OVJP)沈積(例如闡述於美國專利申請案第10/233,470號中者，該案之全文以引用的方式併入本文中)。其他適宜沈積方法包括旋轉塗佈及其他基於溶液之方法。基於溶液之方法較佳在氮氣或惰性氣氛下實施。對於其他層，較佳方法包括熱蒸發。較佳圖案化方法包括藉助掩模沈積、冷銲(例如闡述於美國專利第6,294,398號及第6,468,819號中者，該等專利之全文以引用的方式併入本文中)及與一些沈積方法(例如噴墨及OVJD)相關之圖案化方法。亦可使用其他方法。欲沈積之材料可經修飾以使其能適合特定沈積方法。舉例而言，在小分子中可使用諸如具支鏈或無支鏈且較佳包含至少3個碳原子之烷基及芳基等取代基以增強其進行溶液處理之能力。可使用具有20個碳或更多個碳之取代基，且3－20個碳係較佳範圍。具不對稱結構之材料可較彼等具有對稱結構之材料具有更佳溶液處理能力，此乃因不對稱材料可具有更低重結晶傾向。樹枝狀聚合物取代基可用於增強小分子經受溶液處理之能力。
根據本發明之實施例所製作之裝置可納入各種消費產品中，其包括平板顯示器、電腦監測器、電視、廣告牌、內
部或外部照明燈及/或信號燈、擡頭顯示器、全透明顯示器、撓性顯示器、雷射印刷機、電話、行動電話、個人數位助理(PDA)、膝上型電腦、數位攝影機、攝錄像機、視野取景器、微顯示器、車輛、大面積牆壁、影院或露天大型運動場顯示屏或招牌。可使用各種控制機制來控制根據本發明所製作之裝置，其包括被動矩陣及主動矩陣。許多裝置意欲用於使人感覺舒適之溫度範圍內，例如18攝氏度至30攝氏度，且更佳於室溫下(20－25攝氏度)。
本文所述材料及結構可在除OLED以外之裝置中使用。舉例而言，其他光電子裝置(例如有機太陽能電池及有機光檢測器)可使用該等材料及結構。更一般而言，有機裝置(例如有機電晶體)可使用該等材料及結構。
術語鹵基、鹵素、烷基、環烷基、烯基、炔基、芳烷基、雜環基團、芳基、芳族基團及雜芳基已為該項技術所習知，且定義於美國專利第7,279,704號第31－32行中，其以引用的方式併入本文中。
本發明提供包含具有光活性有空間需求之環金屬化配位基之叁Ir(III)錯合物的化合物。使用具有諸如烷基及芳基等取代基之配位基的優點在於其可提供發光及裝置性質調節同時僅對裝置運行穩定性造成較小的影響。尤其是，將經芳基及烷基取代之配位基納入叁錯合物可用於達成具有高效率及高穩定性之裝置。參見Kwong等人之Complexes with phenylpyridine derivatives and their use in organic light－emitting devices
,2006,WO 2006/014599及Kwong等
人之Stable and efficient electroluminescent materials
,2006,WO 2006/014599 A2。
許多可納入基於Ir之磷光體的環金屬化配位基並不能藉由所報道之合成方法獲得叁－配位基錯合物。在許多情況下，叁配位基錯合物作為磷光材料明顯優於具有兩個環金屬化配位基及單一雙齒或兩個單齒輔助配位基之錯合物。不欲受限於理論，認為Ir與環金屬化配位基之間之鍵較穩定，此意味著其不會容易地被置換，從而改良發光效率。參見Lamansky等人之Synthesis and Characterization of Phosphorescent Cyclometallated Iridium Complexes
,Inorg.Chem.,40：1704－1711,2001及Kwong等人之Organic Light Emitting Devices Having Reduced Pixel Shrinkage
,col.16,ln.45－60,2006、美國專利第7,087,321 B2號。因此，極其期望提供以經改良產率製備具有選擇用於OLED中之光活性配位基的Ir(III)錯合物的方法。此合成對於具有下式之發射Ir(III)錯合物而言尤其困難：
其中R3
、R4
、R5
、R6
、R' 3
、R' 4
、R' 5
及R'6
獨立選自由以下組成之群：氫、烷基、烯基、炔基、烷基芳基、CN、CO2
R、C(O)R、NR2
、NO2
、OR、鹵基、芳基、雜芳基、經取代芳基、經取代雜芳基及雜環基團；且其中R6
與R'3
中
至少一個不為氫，且R6
與R'3
係選自由以下組成之群：烷基、烯基、炔基、烷基芳基、CN、CO2
R、C(O)R、NR2
、NO2
、OR、鹵基、芳基、雜芳基、經取代芳基、經取代雜芳基及雜環基團。由於在最終叁環金屬化Ir錯合物中靠近Ir之多個R6
及/或R'3
使空間擁擠，故該環金屬化配位基與Ir(acac)3
之直接錯合可導致期望產品的產率極低(約10%)。參見Kwong等人之Complexes with phenylpyridine derivatives and their use in organic light－emitting devices
,2006,WO 2006/014599。目前途徑之方案繪示於以下：
據報導此反應具有5.4%產率。
所提供具有烷基及/或芳基取代之錯合物可具有均配或異配性質，其可用於PHOLED裝置中，從而獲得具有較飽和色彩之穩定及有效裝置。該等材料可有利地在PHOLED裝置中用作發射摻雜物。異配錯合物在一些情況中可由於不同配位基賦予期望性質而有利。舉例而言，假設包含Ir(L1
)3
作為發射體之第一裝置與包含Ir(L2
)3
作為發射體之第二裝置相當，其中該第一裝置更穩定且兩個裝置發射相似顏色。但若L1
具有比L2
高的分子量，則Ir(L1
)3
將需要比Ir(L2
)3
高的真空蒸發溫度，由此降低使用Ir(L1
)3
之吸引力。在此情況下，異配Ir(L1
)(L2
)2
或Ir(L1
)2
(L2
)錯合物可具有由各個配位基所賦予之合意特徵(即，L1
賦予良好穩定
性，而L2
賦予降低之分子量及較低之蒸發溫度)。而且，在另一情況下，若Ir(L1
)3
不溶而Ir(L2
)3
溶於大多數有機溶劑，則Ir(L1
)3
不能用於基於溶液之裝置製作方法(例如噴墨印刷)中。在此情況下，異配Ir(L1
)(L2
)2
或Ir(L1
)2
(L2
)錯合物可具有良好穩定性(由L1
所賦予)及良好溶解性(由L2
所賦予)二者。具不對稱結構之異配錯合物可具有比彼等具有對稱結構之均配結構者好的溶液處理能力，此乃因不對稱材料具有較低重結晶傾向。因此，異配化合物與均配化合物相比可提供具有經改良製造、製作、穩定性、效率及/或色彩之裝置。
如圖3中所示，提供可有利地用於OLED中之異配化合物，其具有下式：
其中n＝1或2；R1
、R2
、R3
、R4
及R5
獨立選自由氫、烷基及芳基組成之群，且其中R1
、R2
、R3
、R4
及R5
中每一個皆可代表單、二、三、四或五取代；且R1
、R2
、R3
、R4
及R5
中至少一個為烷基或芳基。
本發明提供可有利地用於OLED中之特定異配化合物：
此外，提供可有利地用於OLED裝置中之異配化合物，其具有下式：
其中n＝1或2；R1
、R2
、R5
及R6
獨立選自由氫、烷基及芳基組成之群；R1
、R2
、R5
及R6
中至少一個為烷基或芳基；且R3
、R4
及R7
獨立選自由氫、烷基及芳基組成之群，且其中R3
、R4
及R7
可代表單、二、三、四或五取代。
本發明提供可有利地用於OLED中之異配化合物：
此外，提供可有利地用於OLED裝置中之異配化合物，其具有下式：
其中n＝1或2；R1
、R2
、R5
及R6
獨立選自由氫、烷基及芳基組成之群；R1
、R2
、R5
及R6
中至少一個為烷基或芳基；且R3
、R4
及R7
獨立選自由氫、烷基及芳基組成之群，且其中R3
、R4
及R7
中每一個皆可代表單、二、三、四或五取代。
本發明提供可有利地用於OLED中之特定異配化合物：
此外，提供可有利地用於OLED裝置中之異配化合物，其具有下式：
其中n＝1或2；R1
及R4
獨立選自由氫、烷基及芳基組成之群；R1
及R4
中至少一個為烷基或芳基；且R2
、R3
及R5
獨立選自由氫、烷基及芳基組成之群，且其中R2
、R3
及R5
中每一個皆可代表單、二、三、四或五取代。
本發明提供可有利地用於OLED中之特定異配化合物：
此外，提供可有利地用於OLED裝置中之異配化合物，其具有下式：
其中n＝1或2；R1
、R2
、R3
、R4
、R5
及R6
獨立選自由氫、烷基及芳基組成之群，且其中R1
、R2
、R3
、R4
、R5
及R6
中每一個皆可代表單、二、三、四或五取代；R1
、R2
、R3
、R4
及R5
中至少一個為烷基或芳基；且至少R1
不同於R4
，R2
不同於R5
或R3
不同於R6
。
本發明提供可有利地用於OLED中之特定異配化合物：
此外，提供可有利地用於OLED中之特定均配化合物，其具有下式：
此外，提供其中化合物包括選自由以下組成之群之配位基的化合物：
其中該配位基配位至原子序數大於40之金屬。較佳地，該金屬係銥。
此外，本發明提供有機發光裝置。該裝置包含陽極、陰極及佈置於該陽極與該陰極之間之有機發射層，該有機層進一步包含發射摻雜物，其中上述化合物係該發射摻雜物。該有機發射層進一步包含主體材料，其中該主體材料係包含咔唑基團、聯伸三苯基團或二苯并噻吩基團之化合物。特定而言，該主體材料係化合物H或化合物G。
本發明提供其中化合物11或化合物35為該發射摻雜物且化合物H或化合物G為該主體材料之特定裝置。
亦提供用於OLED發射層之特定發射摻雜物，此可導致具有尤其良好的性能之裝置。特定而言，具有使用化合物
25或26作為發射摻雜物之發射層的裝置如下表1中所示。分別使用化合物25及26作為發射體之裝置展示經改良之裝置穩定性，此表明烷基苯基取代可助益。Cmpd.係化合物之縮寫。
5'－苯基上之烷基取代可用於轉變蒸發溫度及穩定性，使發射變窄，且使裝置效率增加。僅具有經取代之2－苯基吡啶中之一的化合物25及26的異配性質使蒸發溫度保持低溫(如表1中所示)，此對於OLED製造很重要，因為需要使該等材料延長加熱，且低蒸發溫度轉移成較少的熱應力，此通常造成較完全之蒸發。5'－苯基上之烷基取代亦可增加溶解性(如表1中所示)，此在基於溶液方法之裝置製作中很關鍵(如噴墨印刷)。5'烷基苯基亦可使發射變窄，以用於顯示器應用之OLED中較佳，因為可達成更飽和的色彩。此外，使用化合物25及26之裝置證明使用異配錯合物可給予高裝置效率。
同樣地，具有使用異配化合物6、35、11、18或2作為摻雜物之發射層的裝置可導致具有尤其良好的性質之裝置。特定而言，裝置具有使用化合物6作為摻雜物之發射層、以化合物35作為摻雜物之發射層、以化合物35作為摻雜物且化合物H作為主體材料之發射層、以化合物35作為摻雜物且化合物G作為主體材料之發射層、以化合物11作為摻雜物且化合物H作為主體材料之發射層、以化合物11作為摻雜物且化合物G作為主體材料之發射層、以化合物18作為摻雜物之發射層、及/或以化合物2作為摻雜物之發射
層。該等裝置時常具有一或多項裝置穩定性、發光線寬或裝置效率的改良，如表1中所示。
本發明提供特別的Ir(6－烷基ppy)型化合物，其可導致具有特別窄的發光線寬之裝置。特定而言，裝置使用異配化合物35或11作為發射摻雜物，如表1中所示。據信在6位之取代具有此作用，因為其致力空間效應於Ir錯合物，造成相對較長N－Ir鍵，其轉移成較窄的發射。因此，使Ir(ppy)化合物具有6－烷基且以異配性質特別有用於達成窄發光線寬及經改良之裝置穩定性，而與均配對應物相比未顯著增加蒸發溫度。
本發明提供製備Ir(La
)(Lb
)(Lc
)錯合物之方法，該方法包含使具有式(La
)(Lb
)IrX之中間體與Lc
反應以產生Ir(La
)(Lb
)(Lc
)錯合物，其中La
、Lb
及Lc
獨立為具有下式之雙齒環金屬化配位基：
其中R3
、R4
、R5
、R6
、R'3
、R'4
、R'5
及R'6
獨立選自由以下組成之群：氫、烷基、烯基、炔基、烷基芳基、CN、CO2
R、C(O)R、NR2
、NO2
、OR、鹵基、芳基、雜芳基、經取代芳基、經取代雜芳基或雜環基團；其中R6
或R'3
中至少一個不為氫，且R6
或R'3
係選自由以下組成之群：烷基、烯基、炔基、烷基芳基、CN、CO2
R、
C(O)R、NR2
、NO2
、OR、鹵基、芳基、雜芳基、經取代芳基、經取代雜芳基及雜環基團；且
製備具有式Ir(La
)(Lb
)(Lc
)之錯合物的方法實例包括其中(La
)、(Lb
)及(Lc
)係光活性之錯合物。
製備具有式Ir(La
)(Lb
)(Lc
)之錯合物的方法實例包括其中R'6
為氫、且R3
係選自由烷基、烯基、炔基、烷基芳基、CN、CO2
R、C(O)R、NR2
、NO2
、OR、鹵基、芳基、雜芳基、經取代芳基、經取代雜芳基及雜環基團組成之群之La
、Lb
及Lc
。產率為至少30%或至少50%。
製備具有式Ir(La
)(Lb
)(Lc
)之錯合物的方法實例包括其中R3
為氫、且R'6
選自由烷基、烯基、炔基、烷基芳基、CN、CO2
R、C(O)R、NR2
、NO2
、OR、鹵基、芳基、雜芳基、經取代芳基、經取代雜芳基及雜環基團組成之群之La
、Lb
及Lc
。產率至少為10%。
製備具有式Ir(La
)(Lb
)(Lc
)之錯合物的方法實例包括La
、Lb
及Lc
相同者。
製備具有式Ir(La
)(Lb
)(Lc
)之錯合物的方法實例包括其中R6
為甲基且R3
、R4
、R5
、R'3
、R'4
、R'5
及R'6
皆為氫之La
、Lb
及Lc
。
製備具有式Ir(La
)(Lb
)(Lc
)之錯合物的方法實例包括其中R'3
為甲基、R'5
為甲基、R4
為甲基且R3
、R5
、R6
、R'4
及R'6
皆為氫之La
、Lb
及Lc
。
製備具有式Ir(La
)(Lb
)(Lc
)之錯合物的方法實例包括其中R'3
為甲基、R'5
為甲基、且R3
、R4
、R5
、R6
、R'4
、及R'6
皆為氫之La
、Lb
及Lc
。
如以上段落中所討論，具有空間需求配位基之銥錯合物的產率可藉由其中使中間體Ir(L2
)t
Buacac與L反應以產生IrL3
之方法來改良。舉例而言，該Ir(L2
)t
Buacac中間體方法以經改良產率獲得化合物17、化合物32及化合物11合成中之中間體I。自Ir(L2
)t
Buacac至IrL3
錯合物之反應展示於圖4中。同樣地，具有式Ir(La
)(Lb
)(Lc
)之化合物的經改良產率可藉由使中間體Ir(La
)(Lb
)t
Buacac與Lc
反應來改良。
一些均配及異配經烷基及/或芳基取代之銥化合物係如下合成：化合物1
步驟1.將10克(67.5毫莫耳)2,4－二氯吡啶、9克(74毫莫耳)苯基硼酸、28克(202毫莫耳)碳酸鉀、250毫升二甲氧基乙烷及150毫升水在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。添加2.3克(2.0毫莫耳)Pd(PPh3
)4
並將混合物加熱回流20小時。冷卻至室溫後，將反應混合物用乙酸乙酯萃取並經硫酸鎂亁燥。將產物利用5%乙酸乙酯及己烷進行管
柱層析。管柱後獲得9.2(72%產率)產物。
步驟2.將8.8克(46毫莫耳)4－氯－2－苯基吡啶、7克(69毫莫耳)異丁基硼酸、298克(138毫莫耳)磷酸鉀、1.5克(3.68毫莫耳)2－二環己基膦基－2',6'_二甲氧基聯苯、100毫升甲苯在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。添加0.84克(0.92毫莫耳)Pd2
(dba)3
並將混合物加熱回流4小時。冷卻至室溫後，藉助矽藻土床過濾反應混合物。將產物利用5%乙酸乙酯及己烷進行管柱層析。管柱後獲得8.3克產物(85%產率)。
步驟3.將7.3克(34.5毫莫耳)4－異丁基－2－苯基吡啶及3.4克(6.9毫莫耳)Ir(acac)3
於50毫升乙二醇中加熱回流24小時。冷卻至室溫後，添加100毫升甲醇。藉由過濾收集沈澱物。藉由管柱使用1：1二氯甲烷及己烷作為溶析液純化固體。管柱純化後獲得3.1克產物(55%產率)。將產物藉由於240℃下高真空昇華進一步純化。
化合物2
步驟1.將2.1克(2.6毫莫耳)叁[4－異丁基－2－苯基吡啶]銥(III)溶於100毫升二氯甲烷中。向此溶液中逐滴添加0.45克(2.6毫莫耳)於二氯甲烷中之N－溴琥珀醯亞胺。於室溫下攪拌過夜後，將反應濃縮成50毫升溶劑並自甲醇沈澱。將固體在真空下亁燥且未進一步純化即用於下一步驟。收集到2.1克產物，其包含71%的單溴化化合物。
步驟2.將2.1克來自步驟1之溴化銥錯合物混合物、1.2克(4.6毫莫耳)戊醯二硼、0.68克(6.9毫莫耳)乙酸鉀、100毫升二噁烷在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。向混合物中添加0.06克(0.07毫莫耳)Pd(dppf)2
Cl2
。將反應於90℃下加熱15小時。藉由TLC監測該反應。反應完成後，蒸發掉溶劑。殘餘物利用1：1二氯甲烷及己烷進行管柱純化。獲得1.1克產物。
步驟3.將1.1克(1.16毫莫耳)硼酸酯、0.55克(3.5毫莫耳)溴苯、0.8克(3.48毫莫耳)磷酸鉀、0.02克(0.046毫莫耳)2－二環己基膦基－2',6'_二甲氧基聯苯、60毫升甲苯及6毫升水在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。添加0.01克(0.01毫莫耳)Pd2
(dba)3
並將混合物加熱回流4小時。冷卻至室溫後，藉助矽藻土床過濾反應混合物。將產物利用1：1二氯甲烷及己烷進行管柱純化。管柱後獲得1.0克產物。將產物藉由於260℃下高真空昇華進一步純化。
化合物3
步驟1.將叁(4－甲基－2－苯基吡啶)銥(III)(1.3克，1.9毫莫耳)、N
－溴琥珀醯亞胺(0.33克，1.9毫莫耳)溶於400毫升二
氯甲烷中。將混合物用氮氣吹掃10分鐘並於室溫下在黑暗中攪拌過夜。在減壓下蒸發掉溶劑。用甲醇洗滌殘餘物。獲得1.4克(95%產率)黃色固體混合物。
步驟2.將來自步驟1之溴化Ir錯合物混合物(1.3克，1.7毫莫耳)、戊醯二硼(0.85克，3.4毫莫耳)、乙酸鉀(0.5克，5.1毫莫耳)、及無水二噁烷(100毫升)混合並用氮氣吹掃15分鐘。然後添加Pd(dppf)2
Cl2
(42毫克，0.05毫莫耳)並將混合物用氮氣再吹掃10分鐘。於90℃下加熱過夜後，將混合物冷卻至室溫並在減壓下蒸發。將粗產物藉由二氧化矽管柱利用至多30%於己烷中之CH2
Cl2
純化，獲得0.9克黃色固體(64%產率)。
步驟3.將來自步驟2之產物、溴苯(0.41克，2.6毫莫耳)、2－二環己基膦基－2',6'－二甲氧基聯苯(14.4毫克，0.035毫莫耳)、磷酸三鉀(557毫克，2.6毫莫耳)、甲苯(60毫升)及水(20毫升)混合並用氮氣吹掃15分鐘。然後添加Pd2
(dba)3
並將混合物用氮氣再吹掃10分鐘。回流過夜之後，收集有機層並利用MgSO4
亁燥。將粗產物藉由二氧化矽管柱利用1：1
CH2
Cl2
及己烷來純化，獲得0.6克黃色固體(89%產率)。將該產物藉由於260℃下高真空昇華進一步純化。
化合物4
步驟1.將2,4－二氯吡啶(10克，67.6毫莫耳)、聯苯－3－基硼酸(13.4克，67.6毫莫耳)、乙酸鈀(0.5克，2毫莫耳)、三苯基膦(2.1克，8.1毫莫耳)、碳酸鉀(28克，203毫莫耳)、二甲氧基乙烷120毫升及水40毫升在300毫升3頸燒瓶中混合。將系統用氮氣吹掃15分鐘且然後回流過夜。將反應冷卻至室溫後，收集有機層，經MgSO4
亁燥並在減壓下蒸發。將粗產物藉由二氧化矽管柱利用至多10%於己烷中之乙酸乙酯溶析來純化，獲得12.2克黃色油狀物(68%產率)。
步驟2.將2－(聯苯－3－基)－4－氯吡啶(12.2克，45.9毫莫耳)、異丁基硼酸(5.6克，55.1毫莫耳)、磷酸三鉀(29克，138毫
莫耳)、甲苯(300毫升)混合。將系統用氮氣吹掃15分鐘。然後添加2－二環己基膦基－2',6'－二甲氧基聯苯(0.8克，1.8毫莫耳)及Pd2
(dba)3
(0.4克，0.5毫莫耳)。將系統用氮氣再吹掃5分鐘。回流過夜之後，將反應冷卻至室溫並用水洗滌。經MgSO4
亁燥合併的有機層並在減壓下蒸發。將粗產物藉由二氧化矽管柱利用至多5%於己烷中之乙酸乙酯溶析來純化，獲得3.5克黃色油狀物(27%產率)作為產物。
步驟3.將2－(聯苯－3－基)－4－異丁基吡啶(1克，3.5毫莫耳)、Ir(acac)3
(0.4克，0.9毫莫耳)及乙二醇(10毫升)混合。將系統抽真空並利用氮氣重新充滿，如此3次。於220℃(沙浴溫度)下加熱過夜後，將反應冷卻至室溫。藉由過濾收集黃色沈澱物並用甲醇洗滌。將粗產物藉由二氧化矽管柱利用1：1二氯甲烷及己烷溶析來純化，獲得440毫克黃色固體(46%產率)。將產物藉由於280℃下高真空昇華進一步純化。
化合物5
步驟1.將2－溴－5－氯吡啶(12.0克，62.3毫莫耳)、聯苯－3－基硼酸(14.9克，75毫莫耳)、乙酸鈀(0.035克，2.5莫耳%)、三苯基膦(0.8克，5莫耳%)及碳酸鉀(26.0克，188毫莫耳)放置於500毫升3頸燒瓶中。將150毫升二甲氧基乙烷及150毫升H2
O添加於該燒瓶中。使氮氣吹掃穿過該溶液持續30分鐘且然後使該溶液於氮氣氣氛中回流8小時。然後使反應冷卻至室溫並將有機相與水相分離。將水相用乙酸乙酯洗滌並將有機部分合併並經硫酸鎂亁燥並在真空下去除溶劑。將產物使用二氧化矽凝膠利用乙酸乙酯及己烷作為溶析液進行層析。去除溶劑，獲得14.5克白色固體(88%產率)。
步驟2.將2－(聯苯－3－基)－5－氯吡啶(5.0克，19.0毫莫耳)、異丁基硼酸(4.0克，0.38毫莫耳)、Pd2
(dba)3
(0.20克，1莫耳%)、2－二環己基膦基－2',6'－二甲氧基聯苯(0.31克，4莫耳%)、磷酸鉀單水合物(13克，57毫莫耳)在250毫升圓底燒
瓶中混於100毫升甲苯中。使氮氣吹掃穿過該溶液持續20分鐘並使混合物在氮氣氣氛中回流過夜。將反應混合物冷卻並於真空下去除溶劑。將粗產物使用二氧化矽凝膠管柱利用2%於己烷中之乙酸乙酯作為溶析液進行層析。然後在真空下去除溶劑，獲得4克產物。
步驟3.將2－(聯苯－3－基)－5－異丁基吡啶(4.0克，14.0毫莫耳)及Ir(acac)3
(1.7克，3.5毫莫耳)及10毫升乙二醇放置於100毫升圓底燒瓶中。使反應混合物於220℃下在氮氣氣氛中回流過夜。使反應混合物冷卻並將10毫升甲醇添加於該混合物中。過濾沈澱物並用甲醇洗滌。將產物使用二氧化矽凝膠管柱利用二氯甲烷及己烷(50：50)作為溶析液進行層析。獲得1.3克產物(36%產率)。
化合物6
步驟1.將2－溴－5－甲基吡啶(100克，581毫莫耳)、苯基硼酸(85.2克，700毫莫耳)、乙酸鈀(0.4克，2.5莫耳%)、三苯基膦(7.6克，5莫耳%)及碳酸鉀(240.0克，1740毫莫耳)於600毫升二甲氧基乙烷及600毫升水中之混合物用氮氣吹掃30分鐘並在氮氣下加熱回流8小時。然後使反應冷卻至室溫並將有機相與水相分離。水相用乙酸乙酯洗滌並將有機部分合併並經硫酸鎂亁燥並在真空下去除溶劑。將產物使用二氧化矽凝膠利用乙酸乙酯及己烷作為溶析液進行管柱層析。去除溶劑，獲得90.0克澄清液體(92%產率)。
步驟2.將2－苯基－5－甲基吡啶(10.0克，59.0毫莫耳)及Ir(acac)3
(10.0克，20.4毫莫耳)及20毫升乙二醇放置於100毫升圓底燒瓶中。使反應混合物於220℃下在氮氣氣氛中回流過夜。使反應混合物冷卻並將10毫升甲醇添加於該混合物中。過濾沈澱物並用甲醇洗滌。將產物使用二氧化矽凝膠管柱利用二氯甲烷及己烷(50：50)作為溶析液進行管柱層析。獲得5.94克產物(42%產率)。
步驟3.將叁(2－苯基－4－甲基吡啶)銥(III)(4.4克，5.4毫莫耳)溶於600毫升二氯甲烷中。在15分鐘時期內逐滴添加於二氯甲烷中之N－溴琥珀醯亞胺(0.96克，5.4毫莫耳)。將反應混合物於室溫下攪拌2小時。使反應體積減至200毫升並添加200毫升乙醇以使產物沈澱。將固體過濾並空氣亁燥過夜且未經進一步純化即用於下一步驟。收集到4.8克產物，其包含約71%的單溴化化合物。
步驟4.將來自步驟3之溴化混合物(5.0克，6.5毫莫耳)、戊醯二硼(3.27克，12.9毫莫耳)、乙酸鉀(2.0克，20毫莫耳)及200毫升二噁烷在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。然後添加Pd(dppf)2
Cl2
(0.16克，3莫耳%)。將反應於90℃下加熱15小時。反應完成後，蒸發掉溶劑。將殘餘物使用二氧化矽凝膠管柱首先利用1：1二氯甲烷及己烷作為溶析液、隨後60：40二氯甲烷及己烷進行管柱層析。獲得1.9克產物。
步驟5.將Ir硼酸酯(2.2克，2.7毫莫耳)、溴苯(0.85克，5.4毫莫耳)、磷酸鉀(1.86克，8.1毫莫耳)、2－二環己基膦基－2',6'_二甲氧基聯苯(0.06克，5莫耳%)、100毫升甲苯及10毫升水在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。將Pd2
(dba)3
(0.02克，1莫耳%)添加於反應混合物中，然後使其回流2小時。將反應冷卻至室溫並藉助矽藻土塞過濾。將殘餘物使用二氧化矽凝膠管柱利用1：1二氯甲烷及己烷作為溶析液進行管柱層析。獲得1.5克產物。
化合物7
步驟1.將2－溴－5－氯吡啶(15.0克，77.94毫莫耳)、苯基硼酸(11.4克，93.53毫莫耳)、三苯基膦(2.04克，7.79毫莫耳)
及碳酸鉀(26.9克，194.9毫莫耳)於150毫升二甲氧基乙烷及100毫升水中之混合物用氮氣吹掃20分鐘。添加乙酸鈀(0.87克，3.90毫莫耳)並將反應混合物在氮氣下加熱回流過夜。將反應混合物冷卻並藉助矽藻土過濾。將矽藻土用水及乙酸乙酯洗滌。將該等層分離，且水層用乙酸乙酯萃取。將有機層經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用0至3%乙酸乙酯/己烷溶析來純化該殘餘物。獲得11.8克(80%產率)白色固體。
步驟2.將2－苯基－5－氯吡啶(11.8克，62.22毫莫耳)、異丁基硼酸(12.7克，124.44毫莫耳)、2－二環己基膦基－2',6'－二甲氧基聯苯(1.02克，2.49毫莫耳)及磷酸三鉀(39.62克，186.66毫莫耳)於300毫升甲苯及100毫升水中之混合物用氮氣吹掃20分鐘，之後添加Pd2
(dba)3
(0.57克，0.62毫莫耳)。將混合物於氮氣下回流過夜。將冷卻的混合物藉助矽藻土過濾並將矽藻土用水及乙酸乙酯洗滌。將該等層分離且水層用乙酸乙酯萃取。有機層經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用0及2%乙酸乙酯/己烷溶析來純化該殘餘物。獲得11.05克(84%產率)白色固體。
步驟3.將2－苯基－5－異丁基吡啶(6.86克，32.47毫莫耳)及Ir(acac)3
(3.16克，6.46毫莫耳)於100毫升乙二醇中之混合物於210℃下加熱過夜。使反應冷卻並添加甲醇且濾出黃色固體。藉由管柱層析利用20與40%二氯甲烷/己烷溶析來純化該固體。獲得3.4克(64%產率)產物。
化合物8
步驟1.將2－溴－5－氯吡啶(15.0克，77.94毫莫耳)、苯基硼酸(11.4克，93.53毫莫耳)、三苯基膦(2.04克，7.79毫莫耳)及碳酸鉀(26.9克，194.9毫莫耳)於150毫升二甲氧基乙烷及100毫升水中之混合物用氮氣吹掃20分鐘。添加乙酸鈀(0.87克，3.90毫莫耳)並將反應混合物在氮氣下加熱回流
過夜。將反應混合物冷卻並藉助矽藻土過濾。將矽藻土用水及乙酸乙酯洗滌。將該等層分離，且水層用乙酸乙酯萃取。將有機層經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用0至3%乙酸乙酯/己烷溶析來純化該殘餘物。獲得11.8克(80%產率)白色固體。
步驟2.將2－苯基－5－氯吡啶(11.8克，62.22毫莫耳)、2－甲基丙基硼酸(12.7克，124.44毫莫耳)、2－二環己基膦基－2',6'_二甲氧基聯苯(1.02克，2.49毫莫耳)、磷酸三鉀(39.62克，186.66毫莫耳)於300毫升甲苯及100毫升水中之混合物用氮氣吹掃20分鐘，之後添加Pd2
(dba)3
(0.57克，0.62毫莫耳)。使混合物於氮氣下回流過夜。將冷卻的混合物藉助矽藻土墊過濾並將矽藻土用水及乙酸乙酯洗滌。將該等層分離，且水層用乙酸乙酯萃取。有機層經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用0及2%乙酸乙酯/己烷溶析來純化該殘餘物。獲得11.05克(84%產率)白色固體。
步驟3.將2－苯基－5－異丁基吡啶(6.86克，32.47毫莫耳)及
Ir(acac)3
(3.16克，6.46毫莫耳)於100毫升乙二醇中之混合物於210℃下加熱過夜。使反應冷卻並添加甲醇且濾出黃色固體。藉由管柱層析利用20與40%二氯甲烷/己烷溶析來純化該固體，獲得3.4克產物(64%產率)。
步驟4.將叁(2－苯基－4－異丁基吡啶)銥(III)(4.5克，6.5毫莫耳)溶於600毫升二氯甲烷中。在15分鐘時期內逐滴添加於二氯甲烷中之N－溴琥珀醯亞胺(1.16克，6.5毫莫耳)。將反應混合物於室溫下攪拌2小時。使反應體積減至200毫升並添加200毫升乙醇以使產物沈澱。將固體過濾並空氣亁燥過夜且未經進一步純化即用於下一步驟。收集到4.9克產物，其包含約71%的單溴化化合物。
步驟5.將溴化混合物(4.8克，5.3毫莫耳)、戊醯二硼(2.71克，18.7毫莫耳)、乙酸鉀(1.6克，16.3毫莫耳)及200毫升二噁烷在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。然後添加Pd(dppf)2
Cl2
(0.43克，0.53毫莫耳)。將反應於90℃下加熱15小時。反應完成後，蒸發掉溶劑。將殘餘物使用二氧化矽凝膠管柱首先利用1：1二氯甲烷及己烷作
為溶析液、隨後60：40二氯甲烷及己烷進行層析，獲得1.0克產物。
步驟6.將Ir硼酸酯(0.9克，0.9毫莫耳)、溴苯(0.70克，4.7毫莫耳)、磷酸鉀(1.96克，8.2毫莫耳)、2－二環己基膦基－2',6'_二甲氧基聯苯(0.19克，5莫耳%)、100毫升甲苯及10毫升水在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。將Pd2
(dba)3
(0.01克，1莫耳%)添加於反應混合物，然後使其回流2小時。使反應冷卻至室溫並藉助矽藻土塞過濾。使用二氧化矽凝膠管柱利用1：1二氯甲烷及己烷作為溶析液來層析殘餘物。獲得0.5克產物。
化合物9
步驟1.將2－溴－6－甲基吡啶(10.0克，58.0毫莫耳)、3－甲基苯基硼酸(9.3克，70毫莫耳)、乙酸鈀(0.6克，5莫耳%)、
三苯基膦(1.5克，10莫耳%)及碳酸鉀(32.0克，232毫莫耳)放置於500毫升3頸燒瓶中。將100毫升二甲氧基乙烷及100毫升H2
O添加於該燒瓶中。氮氣吹掃穿過該溶液持續20分鐘且然後使溶液在氮氣氣氛中回流8小時。然後使反應冷卻至室溫並將有機相與水相分離。水相用乙酸乙酯洗滌並將有機部分合併並經硫酸鎂亁燥並在真空下去除溶劑。將產物使用二氧化矽凝膠利用乙酸乙酯及己烷作為溶析液進行層析。去除溶劑，獲得8.08克(76%產率)澄清油狀物。
步驟2.將2－(5－甲基苯基)－6－甲基吡啶(10.0克，54.6毫莫耳)及IrCl3
(7.8克，21.8毫莫耳)在250毫升圓底燒瓶溶於100毫升2－乙氧基乙醇與水相應之3：1混合物。氮氣吹掃穿過該溶液持續10分鐘且然後在氮氣下回流16小時。使反應混合物冷卻至室溫且過濾沈澱物並用甲醇洗滌。然後在真空下亁燥二聚體且未經進一步純化即用於下一步驟。真空亁燥後獲得8.6克二聚體。
步驟3.將該二聚體(6.0克，5毫莫耳)、2,4－戊二酮(1.5克，15.0莫耳)及碳酸鉀(7.0克，50.0毫莫耳)添加於200毫
升2－甲氧基乙醇中並回流過夜。在旋轉蒸發器上去除溶劑並將固體重新溶於二氯甲烷中並使用二氧化矽凝膠管柱且二氯甲烷及己烷作為溶析液進行層析。在旋轉蒸發器上去除溶劑且產物用甲醇洗滌並亁燥，獲得5.1克產物。
步驟4.將來自步驟3之產物(2.0克，3毫莫耳)、2－(3－甲基苯基)－6－甲基吡啶(3.4克，6莫耳當量)及碳酸鉀(2.5克，18毫莫耳)放置於100毫升圓底燒瓶中。將反應混合物於250℃下加熱8小時。使反應混合物冷卻並將10毫升甲醇添加於該混合物中。過濾沈澱物並用甲醇洗滌。使用二氧化矽凝膠管柱利用二氯甲烷及己烷(50：50)作為溶析液來層析產物。獲得1.1克產物(50%產率)。
化合物10
步驟1.製備2－氯－6－甲基吡啶(4.1克，32.4毫莫耳)、聯苯－
3－基硼酸(7.7克，38.9毫莫耳)、三苯基膦(0.85克，3.24毫莫耳)、及碳酸鉀(11.2克，81.0毫莫耳)於60毫升二甲氧基乙烷及40毫升水中之混合物。將氮氣通入該混合物中持續20分鐘。添加乙酸鈀(0.36克，1.62毫莫耳)並將反應混合物在氮氣下加熱回流過夜。使反應冷卻並用水及乙酸乙酯進行稀釋。將該等層分離，且水層用乙酸乙酯萃取。有機層經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用0、1及2%乙酸乙酯/己烷溶析來純化該殘餘物。獲得6.9克(87%產率)澄清液體。
製備Ir二聚體(2.0克，1.87毫莫耳)於200毫升二氯甲烷及10毫升甲醇中之混合物。添加三氟甲磺酸銀(1.0克，3.92毫莫耳)並將反應混合物攪拌3小時。濾出綠色固體並用少量二氯甲烷洗滌。將濾液蒸發至亁燥並在高真空下亁燥。將該材料轉移至100毫升燒瓶中並添加來自步驟1之產物(1.8克，7.48毫莫耳)，隨後添加15毫升十三烷。將混合物於190℃下加熱過夜。形成四種化合物。濾出綠色固體並藉由管柱層析利用10、20、40及50%二氯甲烷/己烷溶析純化。獲得0.80克粗化合物34，其進一步藉由管柱層析、自甲苯重結晶及昇華純化，獲得0.26克產物。
化合物11
步驟1.將2－溴－6－甲基吡啶(100.0克，580毫莫耳)、苯基硼酸(80.0克，640毫莫耳)、乙酸鈀(3.3克，2.5莫耳%)、三苯基膦(8.0克，5莫耳%)及碳酸鉀(240克，1740毫莫耳)於600毫升二甲氧基乙烷及600毫升水中之混合物用氮氣吹掃30分鐘且然後使溶液在氮氣下回流8小時。然後使反應冷卻至室溫並將有機相與水相分離。水相用乙酸乙酯洗滌並將有機部分合併並經硫酸鎂亁燥並在真空下去除溶劑。將
產物使用二氧化矽凝膠利用乙酸乙酯及己烷作為溶析液進行管柱層析。去除溶劑，獲得90.5克澄清液體(92%產率)。
步驟2.將2－苯基－6－甲基吡啶(24.0克，142毫莫耳)及氯化銥(III)(20.0克，56.8毫莫耳)在500毫升圓底燒瓶中溶於250毫升2－乙氧基乙醇與水之3：1混合物。將混合物用氮氣吹掃10分鐘且然後於氮氣下回流16小時。使反應混合物冷卻至室溫且過濾沈澱物並用甲醇洗滌。然後在真空下亁燥二聚體且未經進一步純化即用於下一步驟。真空亁燥後獲得16.0克二聚體(50%產率)。
步驟3.將該二聚體(15.0克，13.3毫莫耳)、二新戊醯基甲烷(25.0克，133毫莫耳)、及碳酸鉀(18.0克，133毫莫耳)添加於250毫升1,2－二氯乙烷中並回流24小時。將反應混合物冷卻並於真空下去除溶劑。殘餘物係使用經三乙胺預處理之二氧化矽凝膠進行管柱層析。使用二氯甲烷及己烷(1：1)作為溶析液。獲得17.8克(94%產率)產物。
步驟4.將該Ir錯合物之混合物(10.0克，14.0毫莫耳)放置於100毫升圓底燒瓶中。將2－苯基－6－甲基吡啶(23.0克，1360毫莫耳)及碳酸鈉(7.7克，70.0毫莫耳)在氮氣下在沙浴中(沙溫度為300℃)加熱24小時。然後使反應冷卻並添加甲醇。將混合物過濾並用甲醇洗滌。將粗產物溶於二氯甲烷中並穿過二氧化矽凝膠塞。去除溶劑且產物用甲醇洗滌且然後亁燥，獲得7.2克產物(74%產率)。
步驟5.將叁(2－苯基－6－甲基吡啶)銥(III)(5.0克，7.2毫莫耳)溶於1升二氯甲烷中。在15分鐘時期內逐滴添加於二氯甲烷中之N－溴琥珀醯亞胺(2.6克，15.6毫莫耳)。將反應混合物於室溫下攪拌2小時。使反應體積減至200毫升並添加200毫升乙醇以使產物沈澱。將固體過濾並空氣亁燥過夜且未經進一步純化即用於下一步驟。收集到6.0克產物，其包含約71%的單溴化化合物。
步驟6.將該溴化混合物(6.2克，7.3毫莫耳)、戊醯二硼(7.38克，29毫莫耳)、乙酸鉀(2.14克，21.8毫莫耳)及300毫升二噁烷在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。然後將Pd(dppf)2
Cl2
(0.60克，0.74毫莫耳)添加於該反應混合物中。將反應於90℃下加熱15小時。反應完成後，蒸發掉溶劑。使用二氧化矽凝膠管柱首先利用1：1二氯甲烷及己烷作為溶析液隨後60：40二氯甲烷及己烷來層析殘餘物。獲得0.8克產物。
步驟7.將Ir硼酸酯(0.8克，0.8毫莫耳)、溴苯(1.32克，8.4毫莫耳)、磷酸鉀(5.0克，21.7毫莫耳)、2－二環己基膦基－2',6'－二甲氧基聯苯(0.30克，10莫耳%)於100毫升甲苯及10毫升水中之混合物用氮氣吹掃30分鐘。將Pd2
(dba)3
(0.08克，2莫耳%)添加於該反應混合物中，然後使其回流2小時。使反應冷卻至室溫並藉助矽藻土塞過濾使用二氧化矽凝膠管柱利用1：1二氯甲烷及己烷作為溶析液來層析殘餘物。獲得0.7克產物。
化合物12
步驟1.將2,6－二氯吡啶(25.0克，169毫莫耳)、苯基硼酸(22.7克，186毫莫耳)、乙酸鈀(0.9克，2.5莫耳%)、三苯基膦(2.2克，5莫耳%)及碳酸鉀(70.0克，507毫莫耳)於300毫升二甲氧基乙烷及300毫升水中之混合物用氮氣吹掃30分鐘且然後使溶液在氮氣下回流8小時。然後使反應冷卻至室溫並將有機相與水相分離。水相用乙酸乙酯洗滌並將有機部分合併並經硫酸鎂亁燥並在真空下去除溶劑。將產物使用二氧化矽凝膠利用乙酸乙酯及己烷作為溶析液進行管柱層析。去除溶劑，獲得12.0克白色固體(38%產率)。
步驟2.將2－苯基－6－氯吡啶(12.0克，63.0毫莫耳)、異丁基硼酸(19.5克，190毫莫耳)、Pd2
(dba)3
(0.60克，1莫耳%)、2－二環己基膦基－2',6'－二甲氧基聯苯(0.8克，3莫耳%)、磷酸鉀單水合物(40.0克，189毫莫耳)於200毫升甲苯中之混合物在500毫升圓底燒瓶用氮氣吹掃20分鐘並使混合物在氮氣氣氛中回流過夜。將反應混合物冷卻並於真空下去除溶劑。使用二氧化矽凝膠管柱利用2%於己烷中之
乙酸乙酯作為溶析液來層析粗產物。然後在真空下去除溶劑，獲得12克產物。
步驟3.將2－苯基－6－異丁基吡啶(5.0克，23.7毫莫耳)及氯化銥(III)(2.08克，5.6毫莫耳)於50毫升2－乙氧基乙醇與水之3：1混合物中之混合物用氮氣吹掃10分鐘且然後在氮氣下回流16小時。使反應混合物冷卻至室溫且過濾沈澱物並用甲醇洗滌。然後在真空下亁燥二聚體且未經進一步純化即用於下一步驟。真空亁燥後獲得3.0克二聚體(40%產率)。
步驟4.將該二聚體(2.5克，1.9毫莫耳)在500毫升圓底燒瓶中溶於200毫升二氯甲烷中。將三氟甲磺酸銀(1.0克，3.9毫莫耳)於10毫升甲醇中之溶液添加於該二聚體溶液中。將反應混合物攪拌過夜。將混合物過濾並蒸發濾液，獲得2.9克期望產物。
步驟5.將三氟甲磺酸銥(1.0克，1.3毫莫耳)及2－(聯苯－3－基)吡啶(0.9克，3.4毫莫耳)放置於100毫升圓底燒瓶中。將10毫升乙醇添加於該燒瓶中。將混合物用氮氣吹掃10分鐘且然後於氮氣下回流16小時。使反應冷卻至室溫並添加異丙醇以使產物沈澱。將反應混合物過濾且殘餘物使用二氧化矽凝膠管柱利用1：1二氯甲烷及己烷作為溶析液進行層析。獲得0.7克產物。
化合物13
步驟1.將100克(0.94莫耳)3,4－二甲基吡啶及40克(1.0莫耳)胺化鈉添加於240毫升N,N
,－二甲基苯胺中。在氮氣下攪拌的同時將反應混合物於150℃下加熱7小時。冷卻後，將
反應混合物添加於400毫升冰水中。用乙酸乙酯萃取該混合物。將有機相濃縮並分級蒸餾。獲得40克(35%產率)2－胺基－3,4－二甲基吡啶(藉由GC約78%)與2－胺基－4,5－二甲基吡啶(藉由GC約22%)之白色固體混合物，其未經進一步純化即用於下一步驟。
步驟2.將8.0克(0.065莫耳)步驟1混合物添加於約25毫升60% HBr中，然後於－15℃至－17℃下攪拌。逐滴添加31.0克預冷(約0℃)Br2
(0.2莫耳)並將混合物攪拌20分鐘。於－15℃至－17℃下將11.4克(0.16莫耳)NaNO2
溶於20毫升水中之預冷(0℃)NaNO2
溶液逐滴添加於該反應混合物中。添加後，將反應攪拌1小時。緩慢添加冰冷的25% NaOH溶液直至溶液變成鹼性為止。用乙酸乙酯萃取該混合物。將有機萃取物濃縮並在真空下蒸餾。獲得10.7克(88%產率)2－溴－3,4－二甲基吡啶(約78%)與2－溴－4,5－二甲基吡啶(約22%)之固體混合物，其未經純化即用於下一步驟。
步驟3.30.0克(162毫莫耳)步驟2混合物、34.0克(167毫莫耳)3－溴苯基硼酸、5.0克(4.3毫莫耳)Pd(PPh3
)4
、60克(434毫莫耳)K2
CO3
、130毫升DME及130毫升水。將反應混合物回流20小時並藉由二氧化矽凝膠管柱利用10%於己烷
溶劑中之乙酸乙酯作為溶析液、隨後蒸餾來純化有機萃取物。藉由在己烷中重結晶進一步分離兩種異構體。
步驟4.將1.7克(6.5毫莫耳)2－(3－溴苯基)－3,4－二甲基吡啶、1.2克(7.8毫莫耳)3,5－二甲基苯基硼酸、235毫克(0.203毫莫耳)Pd(PPh3
)4
、2.8克(20.2毫莫耳)K2
CO3
、50毫升DME及50毫升水填充於200毫升燒瓶中並在氮氣下加熱回流過夜。藉由二氧化矽凝膠管柱利用二氯甲烷作為溶析液來純化有機萃取物。獲得1.5克(81%產率)產物。
步驟5.將4.1克(14.2毫莫耳)來自步驟4之配位基、1.4克(2.86毫莫耳)Ir(acac)3
添加於Schlenk試管中。將該試管於250℃下加熱30小時。藉由二氧化矽凝膠管柱純化反應殘餘物。獲得2.2克(66%產率)產物。
化合物14
步驟1.將3.0克(11.4毫莫耳)來自化合物36之步驟3的2－(3－溴苯基)－3,4－二甲基吡啶、1.8克(12.8毫莫耳)4－氟苯基硼酸、0.4克(0.34毫莫耳)Pd(PPh3
)4
、4.8克(34.7毫莫耳)、K2
CO3
、100毫升DME及100毫升水填充於500毫升燒瓶中並於氮氣下加熱回流過夜。藉由二氧化矽凝膠管柱利用二氯甲烷作為溶析液來純化反應混合物。獲得2.5克(80%產率)產物。
步驟5.將2.3克(8.3毫莫耳)步驟1之配位基、1.02克(2.08毫莫耳)Ir(acac)3
添加於Schlenk試管中。將該試管於250℃下加熱30小時。藉由二氧化矽凝膠管柱純化反應殘餘物。獲得1.3克(63%)固體產物。
化合物15
步驟1.將20.0克(107.5莫耳)來自化合物36步驟2之混合物、17.7克(129毫莫耳)3－甲基苯基硼酸、3.7克(3.2莫耳)(PPh3
)4
、44克(0.321莫耳)K2
CO3
、100毫升DME及100毫升水混合並回流20小時。藉由二氧化矽凝膠管柱利用10%於己烷中之乙酸乙酯作為溶析液來純化有機萃取物。獲得5.1克2－(3－甲基)－4,5－二甲基吡啶，其係藉由NMR及GCMS證實。
步驟2.將4.95克(25.1毫莫耳)來自步驟1之配位基、2.7克(5.57毫莫耳)Ir(acac)3
及40毫升乙二醇填充於200毫升燒瓶中並於氮氣下加熱回流過夜。藉由二氧化矽凝膠管柱利用二氯甲烷作為溶析液純化反應殘餘物。獲得2.6克(60%產率)產物。
化合物16
步驟1.將濃硫酸(27毫升)溶於160毫升水中並冷卻至0℃。然後將4,6－二甲基－2－胺基－吡啶(25克，205毫莫耳)添加於該溶液中。然後緩慢添加亞硝酸鈉(18.4克，266毫莫耳)於40毫升水中之溶液(控制溫度低於5℃)。所有亞硝酸鈉添加完後，將混合物於0℃下攪拌45分鐘，然後於95℃下加熱15分鐘。反應混合物冷卻至室溫後，使用50% w/w NaOH/水將pH值調節至6.5－7.0之範圍內。藉由過濾收集沈澱物並重新溶於二氯甲烷中。用二氯甲烷萃取含水濾液。合併有機萃取物並經MgSO4
亁燥。在減壓下蒸發掉溶劑。將粗產物自400毫升乙酸乙酯重結晶，獲得19.2克(76%產率)黃色固體。
步驟2.將4,6－二甲基吡啶－2－醇(17克，138毫莫耳)溶於300毫升吡啶中。藉由丙酮/冰浴將混合物冷卻至－10℃。藉由氮氣鼓泡至溶液中使反應保持在氮氣下。添加三氟甲磺酸酐(47克，28毫升，166毫莫耳)。將混合物於0℃下攪拌1小時且然後傾倒於300毫升飽和碳酸氫鈉水溶液中(將釋放出一些氣體)。用二氯甲烷萃取該混合物。有機萃取物經MgSO4
亁燥並在減壓下濃縮，獲得33克褐色油狀物(94%產率)。粗產物未進一步純化即用於下一步驟。
步驟3.將三氟甲磺酸4,6－二甲基吡啶－2－基酯(18.8克，74毫莫耳)、苯基硼酸(10.8克，88毫莫耳)、磷酸三鉀(56克，264毫莫耳)、甲苯(550毫升)及水(55毫升)在一個1升3頸燒瓶中混合。將系統用氮氣吹掃15分鐘，然後添加Pd2
(dba)3
(0.81克，0.88毫莫耳)及2－二環己基膦基－2',6'_二甲氧基聯苯(1.45克，3.5毫莫耳)。將系統用氮氣再吹掃10分鐘，然後回流4小時。將反應冷卻至室溫後，收集有機層，經MgSO4
亁燥並在減壓下蒸發。粗產物藉由二氧化矽管柱利用10%於己烷中之乙酸乙酯溶析來純化，獲得12.0克產物(90%產率)。
步驟4.將2.0克(10.9毫莫耳)步驟3配位基及1.1克(2.2毫莫耳)Ir(acac)3
填充於Schlenk試管中並在氮氣下攪拌的同時於250℃下加熱20小時。藉由二氧化矽凝膠管柱利用於己烷中之二氯甲烷50%作為溶析液來純化反應殘餘物。獲得0.6克(34%產率)產物。
化合物17
步驟1.將三氟甲磺酸4,6－二甲基吡啶－2－基酯(18.8克，74毫莫耳)、間－甲苯基硼酸(12克，88毫莫耳)、磷酸三鉀(56克，264毫莫耳)、甲苯(550毫升)及水(55毫升)在一個1升3頸燒瓶中混合。將系統用氮氣吹掃15分鐘，然後添加Pd2
(dba)3
(0.81克，0.88毫莫耳)及2－二環己基膦基－2',6'－二甲氧基聯苯(1.45克，3.5毫莫耳)。將系統用氮氣再吹掃10分鐘，然後回流4小時。將反應冷卻至室溫後，收集有機層，經MgSO4
亁燥並在減壓下蒸發。藉由二氧化矽管柱利用2%於己烷中之乙酸乙酯溶析來純化粗產物，獲得13.3克白色固體(91%產率)。
步驟2.將步驟1之產物(10克，50.6毫莫耳)、氯化銥(4.4克，12.6毫莫耳)、2－乙氧基乙醇(180毫升)及水(60毫升)在500毫升3頸燒瓶中混合。將系統用氮氣吹掃15分鐘，然後回流過夜。反應冷卻至室溫後，在減壓下蒸發掉溶劑。殘餘物用甲醇洗滌，獲得3.7克暗紅色固體(24%產率)。
步驟3.將該二聚體(2.7克，2.2毫莫耳)、二新戊醯基甲烷(4.0克，4.5毫升，21.6毫莫耳)、碳酸鈉(2.3克，21.6毫莫耳)及2－乙氧基乙醇(100毫升)在300毫升3頸燒瓶中混合。將系統用氮氣吹掃20分鐘。然後使反應回流3小時。冷卻至室溫後，使混合物穿過矽藻土塞並用甲醇洗滌。洗去矽藻土中之黃色後，使用二氯甲烷洗滌該矽藻土塞直至濾液變成無色為止。收集二氯甲烷濾液並在減壓下蒸發。藉由二氧化矽管柱(藉由20%於己烷中之三乙胺預處理)利用至多100%於己烷中之二氯甲烷純化粗產物，獲得2克黃色固體(60%產率)。
步驟4.將來自步驟3之產物(1.8克，2.3毫莫耳)、2,4－二甲基－6－間－甲苯基吡啶(4.5克，22.8毫莫耳)、碳酸鈉(1.2克，11.4毫莫耳)混合。將系統抽真空並利用氮氣重新充滿，如此3次。將混合物於270℃(沙浴溫度)下加熱3小時。冷卻至室溫後，將混合物溶於二氯甲烷中並使其穿過矽藻土塞。用二氯甲烷洗滌該矽藻土塞。將合併的部分在減壓下蒸發。藉由二氧化矽管柱用1：2二氯甲烷及己烷溶析來純化粗產物，獲得1克黃色固體。產物藉由於240℃下高真空昇華進一步純化。
化合物18
步驟1.2－溴吡啶(8.66克，54.8毫莫耳)、3－甲氧基苯基硼酸(10克，65.8毫莫耳)、三苯基膦(1.44克，5.48毫莫耳)、碳酸鉀(18.9克，137毫莫耳)於100毫升二甲氧基乙烷及66毫升水中之混合物用氮氣吹掃20分鐘。然後添加乙酸鈀(0.61克，2.74毫莫耳)。將反應混合物在氮氣下加熱回流過夜。將反應混合物冷卻並添加水及乙酸乙酯。將該等層分離，且水層用乙酸乙酯萃取。有機萃取物經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用0至20%乙酸乙酯/己烷溶析來純化該殘餘物。獲得9.7克澄清油狀物(96%產率)。
步驟2.將2－(3－甲氧基苯基)吡啶(9.7克，52.37毫莫耳)及吡啶鹽酸鹽(72.6克，628.44毫莫耳)之混合物於220℃下加熱2小時。將水添加於冷卻的混合物中且然後用二氯甲烷萃取兩次。有機萃取物經硫酸鎂亁燥、過濾及蒸發，得到
殘餘物。藉由管柱層析利用0、1及2%甲醇/二氯甲烷溶析、隨後真空蒸餾並自2：1己烷/乙酸乙酯重結晶來純化該殘餘物。獲得5克白色固體(56%產率)。
步驟3.製備3－(吡啶－2－基)苯酚(5克，29.21毫莫耳)於100毫升二氯甲烷中之溶液。向此溶液中添加吡啶(4.7毫升，58.42毫莫耳)並將溶液在冰－鹽浴中冷卻。向此溶液中逐滴添加三氟甲磺酸酐(9.8毫升，58.42毫莫耳)於20毫升二氯甲烷中之溶液。將反應緩慢加熱且2小時後完成。添加水及二氯甲烷並將層分離。用二氯甲烷萃取水層。有機萃取物經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用5、10、及15%乙酸乙酯/己烷溶析來純化該殘餘物。獲得8克澄清液體(90%產率)。
步驟4.將10.7克(58.5毫莫耳)2－苯基－4,6－二甲基吡啶、5.4克(14.6毫莫耳)氯化銥、150毫升2－乙氧基乙醇及50毫升水在500毫升3頸燒瓶中混合。將系統用氮氣吹掃15分鐘，然後回流過夜。反應冷卻至室溫後，在減壓下蒸發掉溶劑。將殘餘物用甲醇洗滌，獲得4.1克暗紅色固體(46%產率)。
步驟5.將3.0克二聚體(2.5毫莫耳)溶於200毫升二氯甲烷中並添加1.32克(5.1毫莫耳)AgOTf及10毫升甲醇。將反應混合物於室溫下攪拌30分鐘。將殘餘物過濾，用甲醇(2x50毫升)洗滌。將濾液蒸發以獲得黃色固體，其未經任何純化即用於下一步驟。
步驟6.將來自步驟5之產物與3.1克(10.0毫莫耳)步驟3之產物及150毫升2－甲氧基乙醇一起添加。將反應混合物於90℃下加熱18小時。將反應混合物冷卻並藉由二氧化矽凝膠管柱利用40%於己烷中之二氯甲烷作為溶析液來純化。獲得1.6克黃色固體。
步驟9.將1.6克(1.86毫莫耳)步驟6產物、0.86克(7.0毫莫耳)苯基硼酸、35毫克(0.037毫莫耳)Pd2
(dba)3
、62毫克(0.149毫莫耳)2－二環己基膦基－2',6'_二甲氧基聯苯、1.3克(5.6毫莫耳)磷酸三鉀單水合物及150毫升無水甲苯填充於3頸燒瓶中。使氮氣吹掃穿過該反應混合物持續40分鐘，然後加熱回流過夜。有機萃取物係藉由二氧化矽凝膠管柱利
用30%於己烷中之二氯甲烷作為溶析液來純化。獲得1.3克(約90%產率)產物。
化合物19
步驟1.將25克(98毫莫耳)3,5－二溴甲基苯、12.2克(98毫莫耳)苯基硼酸、3.4克(2.9毫莫耳)Pd(PPh3
)4
、41克(297毫莫耳)K2
CO3
、150毫升DME及150毫升水填充於500毫升燒瓶中。將反應混合物在氮氣下加熱回流過夜。藉由二氧化矽凝膠管柱純化有機萃取物。獲得16克(66%產率)產物。
步驟2.在氮氣下將10.2克(41.4毫莫耳)步驟1產物、100毫升(50毫莫耳)0.5M於THF中之吡啶鋅溴化物及1.5克(1.29毫莫耳)Pd(PPh3
)4
添加於亁燥200毫升燒瓶中。使反應在氮氣下回流5小時且藉由二氧化矽凝膠管柱利用10%於己烷中之乙酸乙酯作為溶析液來純化有機萃取物。獲得8.5克(85%產率)產物。
步驟3.將5.2克(21.2毫莫耳)步驟2之產物、2克(4.24毫莫耳)Ir(acac)3
填充於Schlenk試管中並在氮氣下於280℃下加熱48小時。藉由二氧化矽凝膠管柱純化反應殘餘物。獲得0.3克(7.6%產率)產物。
化合物20
步驟1.將2－溴吡啶(40克，253毫莫耳)、3－溴苯基硼酸(61.0克，303.8毫莫耳)、三苯基膦(6.64克，25.3毫莫耳)、碳酸鉀(87.4克，632.5毫莫耳)於300毫升二甲氧基乙烷及200毫升水中之混合物用氮氣吹掃20分鐘。然後添加乙酸鈀(2.84克，12.65毫莫耳)。將反應混合物在氮氣下加熱回流。將反應混合物冷卻並添加水及乙酸乙酯。將該等層分離，且水層用乙酸乙酯萃取。有機萃取物經硫酸鎂亁燥、過濾並蒸發，得到褐色油狀物，將該褐色油狀物藉由管柱
層析利用0至40%乙酸乙酯/己烷溶析、隨後在真空下蒸餾來純化。獲得45.1克(52%產率)產物。
步驟2.將2.5克(10.7毫莫耳)步驟1產物、2.5克(8.0毫莫耳)3,5－二異丙基苯基硼酸、0.3克(0.259毫莫耳)Pd(PPh3
)4
、3.6克(26毫莫耳)K2
CO3
、50毫升DME及50毫升水填充於200毫升燒瓶中。將反應混合物在氮氣下加熱回流過夜。藉由二氧化矽凝膠管柱純化有機萃取物。獲得1.4克(56%產率)產物。
步驟3.將1.3克(4.1毫莫耳)來自步驟2之產物、0.58克(1.17毫莫耳)Ir(acac)3
及20毫升乙二醇添加於100毫升燒瓶中並加熱回流過夜。藉由二氧化矽凝膠管柱純化有機萃取物。獲得0.7克(56%產率)產物。
化合物21
步驟1.將2.5克(10.7毫莫耳)2－(3－溴苯基)吡啶、2.4克(16毫莫耳)3,5－二甲基苯基硼酸、0.37克(0.321毫莫耳)Pd(PPh3
)4
、4.5克(32.6毫莫耳)K2
CO3
、50毫升DME及50毫升水填充於200毫升燒瓶中。將反應混合物在氮氣下加熱回流過夜。藉由二氧化矽凝膠管柱純化有機萃取物。獲得2.3克(83%產率)產物。
步驟2.將2.0克(7.68毫莫耳)步驟1之產物、1.1克(2.14毫莫耳)Ir(acac)3
及20毫升乙二醇添加於100毫升燒瓶中並加熱回流過夜。藉由二氧化矽凝膠管柱純化有機萃取物。獲得1.7克(86%產率)產物。
化合物22
步驟1.將3.5克(15.0毫莫耳)2－(3－溴苯基)吡啶、3.5克(19.7毫莫耳)3,5－二乙基苯基硼酸、0.4克(0.345毫莫耳)Pd(PPh3
)4
、6.2克(44.9毫莫耳)K2
CO3
、100毫升DME及100毫升水填充於250毫升燒瓶中。將反應混合物在氮氣下加熱回流過夜。藉由二氧化矽凝膠管柱純化有機萃取物。獲得3.2克(74%產率)產物。
步驟2.將2.2克(7.64毫莫耳)來自步驟1之產物、1.04克(2.12毫莫耳)Ir(acac)3
及30毫升乙二醇添加於100毫升燒瓶中並加熱回流過夜。藉由二氧化矽凝膠管柱純化有機萃取物。獲得1.5克(67%產率)產物。
化合物23
步驟1.將2－(3－溴苯基)吡啶(15克，64毫莫耳)、3－聯苯硼酸(13.70克，69毫莫耳)、碳酸鉀(27克，195毫莫耳)於100毫升二甲氧基乙烷及60毫升水中之混合物用氮氣吹掃20分鐘。然後添加Pd(PPh3
)4
(2.3克，2毫莫耳)並使反應混合物在氮氣下加熱回流過夜。第二天使反應混合物冷卻並用水及乙酸乙酯稀釋。將該等層分離，且水層用乙酸乙酯萃取。有機層經硫酸鎂亁燥、過濾並蒸發，得到紅色油狀物。藉由管柱層析利用5至30%乙酸乙酯/己烷溶析來純化該油狀物，獲得19克澄清油狀物作為產物。
步驟2.將1.5克(4.8毫莫耳)步驟1配位基、0.68克(1.39毫莫耳)Ir(acac)3
及25毫升乙二醇填充於100毫升燒瓶中。將反應混合物在氮氣下加熱回流過夜。使反應冷卻並過濾，利用甲醇洗滌3次(3x50毫升)。藉由二氧化矽凝膠管柱來純化固體，獲得0.8克(51%)產物。
化合物24
步驟1.將2－(3－溴苯基)吡啶(12.2克，52.10毫莫耳)、3－(4,4,5,5－四甲基－1,3,2－二氧硼－2－基)苯酚(13.76克，62.53毫莫耳)、2－二環己基膦基－2',6'－二甲氧基聯苯(856毫克，2.08毫莫耳)、磷酸三鉀單水合物(36克，156.3毫莫耳)於180毫升二噁烷及18毫升水中之混合物用氮氣吹掃20分鐘。然後添加Pd2
(dba)3
(477毫克，0.52毫莫耳)。將反應混合物在氮氣下於100℃下加熱3小時，然後使其冷卻至室溫過夜。將水添加於反應混合物中並將混合物用乙酸乙酯萃取3次。有機萃取物經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用20及40%乙酸乙酯/己烷溶析來純化該殘餘物，獲得12.5克黃色油狀物(97%產率)作為產物。
步驟2.於0℃下將12.5克(50.6毫莫耳)步驟1產物、12毫升吡啶及200毫升二氯甲烷在500毫升圓底燒瓶中混合物。添加14.3克(101.2毫莫耳)三氟甲磺酸酐。將混合物於0℃下攪拌30分鐘並於室溫下攪拌1小時。將反應混合物用水洗滌若干次。蒸發掉溶劑後獲得19.0克(約100%產率)產物。
步驟3.將8.8克(23.2毫莫耳)來自步驟2之產物、4.7克(46毫莫耳)異丁基硼酸、0.02克Pd2
(dba)3
(0.23毫莫耳)、0.4克(0.965毫莫耳)2－二環己基膦基－2',6'_二甲氧基聯苯、16.7克(72.6毫莫耳)K3
PO4
.H2
O及300毫升甲苯填充於500毫升圓底燒瓶中。在攪拌的同時將反應混合物在氮氣下加熱回流過夜。藉由二氧化矽凝膠層析利用10%於己烷中之乙酸乙酯作為溶析液純化反應混合物。獲得5.8克(產率87%)產物。
步驟4.將2.0克(6.9毫莫耳)來自步驟3之配位基、0.97克(2.0毫莫耳)Ir(acac)3
及25毫升乙二醇填充於100毫升圓底燒瓶中。將反應混合物在氮氣下加熱回流過夜。使反應混合物冷卻並添加100毫升甲醇。將固體過濾，用甲醇洗滌並亁燥。二氧化矽管柱純化後獲得1.3克(62%產率)產物。
化合物25
將2.0克(2.55毫莫耳)Ir(ppy)3
硼酸酯(根據USPTO第11/951,879號製得)、1.6克(7.6毫莫耳)4－異丁基溴苯、0.21克(0.52毫莫耳)2－二環己基膦基－2',6'－二甲氧基聯苯、1.1克
(5.1毫莫耳)磷酸鉀、80毫升甲苯及8毫升水在3頸燒瓶中混合。將混合物用氮氣吹掃30分鐘。向脫氣混合物中添加0.12克(0.127毫莫耳)Pd2
(dba)3
。使反應在氮氣氣氛下回流過夜。冷卻至室溫後，藉助矽藻土床過濾反應混合物。將矽藻土床上之黃色沈澱物用二氯甲烷洗滌。溶液用硫酸鎂亁燥。溶劑蒸發後，藉由管柱使用1：1己烷及二氯甲烷作為溶析液純化殘餘物。獲得1.65克產物。
化合物26
將2.0克(2.55毫莫耳)Ir(ppy)3
硼酸酯、1.35克(7.69毫莫耳)4－甲基溴苯、0.21克(0.52毫莫耳)2－二環己基膦基－2',6'－二甲氧基聯苯、1.6克(7.5毫莫耳)磷酸鉀、80毫升甲苯及8毫升水在3頸燒瓶中混合。將混合物用氮氣吹掃30分鐘。向脫氣混合物中添加0.12克(0.127毫莫耳)Pd2
(dba)3
。使反應在氮氣氣氛下回流過夜。冷卻至室溫後，藉助矽藻土床
過濾反應混合物。將矽藻土床上之黃色沈澱物用二氯甲烷洗滌。溶液用硫酸鎂亁燥。溶劑蒸發後，藉由管柱使用1：1己烷及二氯甲烷作為溶析液純化殘餘物。獲得1.55克(83%產率)產物。
化合物27
步驟1.將10.0克(49.2毫莫耳)4－溴苯乙醇、9.17克(54.1毫莫耳)DAST與150毫升無水二氯甲烷一起填充於亁燥250毫升燒瓶中並將反應混合物在氮氣下於室溫下攪拌20小時。緩慢添加NaHCO3
溶液(40克於300毫升水中)以使反應驟冷。添加後，將其再攪拌2小時直至無CO2
逸出為止。藉由二氧化矽凝膠管柱純化有機萃取物，獲得9克(91%產率)產物。
步驟2.將2.0克(2.55毫莫耳)Ir(ppy)3
硼酸酯、1.0克(5.0毫莫耳)步驟1產物、0.21克(0.52毫莫耳)2－二環己基膦基－2',6'－二甲氧基聯苯、1.6克(7.5毫莫耳)磷酸鉀、80毫升甲苯及8毫升水在3頸燒瓶中混合。將混合物用氮氣吹掃30分鐘。向脫氣混合物中添加0.12克(0.127毫莫耳)Pd2
(dba)3
。使反應在氮氣氣氛下回流過夜。冷卻至室溫後，藉助矽藻土床過濾反應混合物。將矽藻土床上之黃色沈澱物用二氯甲烷洗滌。溶液用硫酸鎂亁燥。溶劑蒸發後，藉由管柱使用1：1己烷及二氯甲烷作為溶析液純化殘餘物，獲得1.65克(85%產率)產物。
化合物28
步驟1.於－78℃下將9.5毫升BuLi(23.75毫莫耳；2.5 M於
己烷中之BuLi)緩慢添加於4.0克(19.7毫莫耳)於100毫升無水THF中之4－(2－氟乙基)溴苯中。將該混合物於－78℃下攪拌1小時，然後於－78℃下添加2.6毫升(23.7毫莫耳)於10毫升無水THF中之B(OMe)3
。使反應升溫至室溫並攪拌過夜。添加60毫升HCl(1 M)並將混合物攪拌3小時。將乙酸乙酯添加於反應溶液中以萃取有機相。將有機相合併並蒸發。獲得白色固體，將其用己烷洗滌並亁燥。所得硼酸未經進一步純化即用於下一步驟。
步驟2.將2.5克(14.8毫莫耳)來自步驟1之硼酸、3.0克(13.5毫莫耳)2－(3－溴苯基)吡啶、0.48克(0.415毫莫耳)Pd(PPh3
)4
、5.6克(40.57毫莫耳)K2
CO3
、50毫升DME及50毫升水添加於200毫升燒瓶中。將反應混合物在氮氣下加熱回流過夜。藉由二氧化矽凝膠管柱純化有機萃取物。獲得3.2克(86%產率)產物。
步驟3.將3.0克(10.8毫莫耳)步驟2之配位基、1.3克(2.7毫莫耳)Ir(acac)3
及50毫升乙二醇添加於100毫升燒瓶中並於氮氣下加熱回流過夜。藉由二氧化矽凝膠管柱純化有機萃
取物。獲得1.65克(60%產率)產物。
化合物29
步驟1.將咔唑(10克，60毫莫耳)、1－溴－2－甲基丙烷(16.4克，120毫莫耳)、KOH(8.4克，150毫莫耳)、18－冠－6(160毫克，0.6毫莫耳)及DMF 50毫升混合並於室溫下攪拌2天。將混合物用400毫升水稀釋並用二氯甲烷萃取3次。將合併的有機層經MgSO4
亁燥並在減壓下蒸發。藉由二氧化矽管柱利用至多5%於己烷中之CH2
Cl2
來純化粗產物，提供12克產物(66%產率)。
步驟2.將9－異丁基－9H－咔唑(12克，53.7毫莫耳)、N－溴琥珀醯亞胺(9.6克，53.7毫莫耳)及300毫升DMF混合並於室溫下攪拌2天。在減壓下蒸發溶劑。將混合物重新溶於二氯甲烷中並用水洗滌。收集有機層並用MgSO4
亁燥，提
供16.7克產物(100%產率)。
步驟3.將3－溴－9－異丁基－9H－咔唑(16.7克，55毫莫耳)、戊醯二硼(28克，110毫莫耳)、乙酸鉀(16克，165毫莫耳)及400毫升無水二噁烷混合並用氮氣吹掃20分鐘。然後添加Pd(dppf)2
Cl2
並將系統用氮氣再吹掃15分鐘。於90℃下加熱過夜後，蒸發溶劑。藉由二氧化矽管柱利用至多10%於己烷中之乙酸乙酯純化粗產物，獲得3克純淨產物(16%產率)。
步驟4.將9－異丁基－3－(4,4,5,5－四甲基－1,3,2－二氧硼－2－基)－9H－咔唑(3.1克，8.9毫莫耳)、溴吡啶(2.8克，17.8毫莫耳)、碳酸鉀(3.7克，26.6毫莫耳)、三苯基膦(0.28克，1.1毫莫耳)、60毫升二甲氧基乙烷及20毫升水在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。然後添加乙酸鈀(60毫克，0.27毫莫耳)並將混合物用氮氣再吹掃15分鐘。回流過夜之後，收集有機層並蒸發掉溶劑。藉由二氧化矽管柱利用至多10%於己烷中之乙酸乙酯純化混合物，獲得2.1克白色固體(79%產率)。
步驟5.將3－苯基－9－異丁基－9H－咔唑(2.1克，7毫莫耳)、Ir(acac)3
(0.86克，1.7毫莫耳)及20毫升乙二醇混合。將混合物抽真空並用氮氣重新充滿，如此3次，且然後於220℃下加熱2天。混合物冷卻至室溫後，添加甲醇以使錯合物沈澱。收集殘餘物並用甲醇洗滌。藉由二氧化矽管柱利用1：1 CH2
Cl2
及己烷來純化粗產物，獲得1.2克黃色固體(65%產率)。產物藉由於290℃下高真空昇華來進一步純化。
化合物30
步驟1.將5.3克(30毫莫耳)2,6－二異丙基苯胺、9.36克(30毫莫耳)2,2'－二溴聯苯、0.99克(2.4毫莫耳)2－二環己基膦基－2',6'－二甲氧基聯苯、8.8克(90毫莫耳)第三丁醇鈉及0.55克(0.6毫莫耳)Pd2
(dba)3
在100毫升二甲苯中混合。使
混合物在氮氣下回流過夜。冷卻至室溫後，藉助矽藻土床過濾反應混合物。將產物利用己烷進行管柱層析。管柱後獲得5.8克產物(59%產率)。
步驟2.將5.7克(17毫莫耳)9－(2,6－二異丙基苯基)－9H－咔唑溶於100毫升DMF中。向該溶液中以小份添加3.1克(17毫莫耳)NBS。使反應反應2小時。添加水以使產物沈澱。將產物用二氯甲烷溶解，用水洗滌，並利用硫酸鎂亁燥。溶劑蒸發後，獲得6.78克產物，根據HPLC其包含約72%產物。產物未經進一步純化直轉用於下一步驟。
步驟3.將6.78克3－溴－9－(2,6－二異丙基苯基)－9H－咔唑、5.8克(23毫莫耳)戊醯二硼、4.9克(50毫莫耳)乙酸鉀、100毫升DMSO在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。向混合物中添加0.4克(0.5毫莫耳)Pd(dppf)2
Cl2
。將反應於80℃下加熱15小時。藉由TLC監測該反應。反應完成後，利用300毫升水沈澱產物。將固體利用1：5二氯甲烷及己烷進行管柱層析。獲得4.3克產物(57%產率)。
將4.3克(9.5毫莫耳)硼酸酯、1.8克(11.4毫莫耳)2－溴吡啶、6.4克(28.5毫莫耳)磷酸鉀、0.16克(0.38毫莫耳)2－二環己基膦基－2',6'－二甲氧基聯苯、100毫升甲苯及10毫升水在3頸燒瓶中混合。將系統用氮氣吹掃30分鐘。添加0.09克(0.09毫莫耳)Pd2
(dba)3
並將混合物加熱回流過夜。將產物利用5%於己烷中之乙酸乙酯進行管柱層析。管柱後獲得1.0克產物。
將0.9克(2.2毫莫耳)9－(2,6－二異丙基苯基)－3－(吡啶－2－基)－9H－咔唑及0.22克(0.45毫莫耳)Ir(acac)3
在20毫升乙二醇中加熱回流48小時。冷卻至室溫後，添加100毫升甲醇。藉由過濾收集沈澱物。將固體藉由管柱使用1：1二氯甲烷及己烷作為溶析液來純化。管柱純化後獲得0.07克產物。產物藉由於350℃下高真空昇華進一步純化。
化合物31
步驟1.將4.5克(21.9毫莫耳)5－溴－2－氟－間－二甲苯、6.2克(24.1毫莫耳)頻哪醇基二硼烷、0.54克(0.66毫莫耳)Pd(dppf)2
Cl2
.CH2
Cl2
、6.4克(65.7毫莫耳)KOAc及100毫升DMSO填充於200毫升燒瓶中。將反應混合物在80℃下在氮氣下加熱過夜。有機萃取物係藉由二氧化矽凝膠管柱利用10%於己烷中之乙酸乙酯作為溶析液來純化。獲得4.3克(79.6%產率)產物。
步驟2.將4.0克(16毫莫耳)步驟1產物、2.3克(14.5毫莫耳)溴吡啶、0.51克(0.44毫莫耳)Pd(PPh3
)4
及6克(43.3毫莫耳)K2
CO3
、50毫升DME及50毫升水添加於250毫升燒瓶中。使反應在氮氣下回流5小時。然後將反應利用二氧化矽凝
膠管柱利用4%於己烷中之乙酸乙酯作為溶析液進行處理。獲得2.8克(96%產率)產物。
步驟3.將2.1克(10.2毫莫耳)步驟2產物及1.27克(2.6毫莫耳)Ir(acac)3
添加於Schlenk試管中並於245℃下在氮氣下加熱28小時。收集沈澱物並藉由二氧化矽凝膠管柱利用25%於己烷中之二氯甲烷作為溶析液進行純化。獲得0.25克(11%產率)產物。
化合物32
步驟1.將12.6克(80毫莫耳)2－溴吡啶、12克(80毫莫耳)3,5－苯基硼酸、0.18克(0.8毫莫耳)乙酸鈀、0.84克(3.2毫莫耳)三苯基膦及33克(240毫莫耳)碳酸鉀、80毫升二甲氧基乙烷及50毫升水用氮氣吹掃並加熱回流12小時。冷卻後，將有機層分離，用水洗滌，並經MgSO4
亁燥。藉由管柱層析使用5%於己烷中之乙酸乙酯作為溶析液分離產
物。
步驟2.將1克(5.45毫莫耳)2－(3,5－二甲基苯基)吡啶及0.53克(1.09毫莫耳)Ir(acac)3
之混合物利用沙浴加熱至外部溫度為290℃保持3小時。將混合物冷卻並溶於二氯甲烷中。將產物亁填塞於矽藻土上並藉由管柱層析使用己烷/二氯甲烷作為溶析液(40%二氯甲烷)分離。收集到0.1克產物。
化合物32之替代方法
步驟1.將6.6克(36毫莫耳)2－(3,5－二甲基苯基)吡啶及4.23克(12毫莫耳)氯化銥、90毫升2－乙氧基乙醇及30毫升水混合並在氮氣下加熱回流過夜。冷卻至室溫後，藉由過濾收集固體，並利用甲醇及己烷充分洗滌。將固體亁燥且未經進一步純化即用於下一步驟。獲得6克期望產物(84%產率)。
步驟2.將6.0克(5毫莫耳)該二聚體、9.2克(50毫莫耳)2,2,6,6－四甲基庚烷－3,5－二酮、2.7克(25毫莫耳)碳酸鈉及100毫升2－乙氧基乙醇在燒瓶中混合並在氮氣下加熱回流4小時。冷卻至室溫後，藉助矽藻土床過濾混合物。將固體用甲醇充分洗滌。將矽藻土床頂部之固體用二氯甲烷溶解。然後使溶液流過三乙胺處理之二氧化矽凝膠塞。溶劑蒸發後，獲得5.9克期望產物(80%產率)。
步驟3.將2.95克(4毫莫耳)t
Buacac錯合物、7.3克(40毫莫耳)2－(3,5－二甲基苯基)吡啶、及2.1克(20毫莫耳)碳酸鈉混合並小心地脫氣。將混合物於270℃下加熱24小時且然後於290℃下6小時。將反應冷卻至室溫。添加30毫升二氯甲烷。將混合物藉助矽藻土過濾。蒸發溶劑並將300毫升己烷添加於殘餘物中。將混合物攪拌過夜。藉由過濾收集固體。去除未反應起始材料。將固體藉由二氧化矽凝膠管柱使用3：1己烷及二氯甲烷作為溶劑進一步純化。純化後獲得0.7克材料。錯合物藉由高真空昇華進一步純化。獲得
0.4克產物。
化合物33
步驟1.將8.1克(51.5毫莫耳)2－溴吡啶、7克(51.5毫莫耳)鄰－甲苯基硼酸、0.47克(0.51毫莫耳)Pd2
(dba)3
、0.84克(2.06毫莫耳)2－二環己基膦基－2',6'－二甲氧基聯苯及32克(154.5毫莫耳)磷酸三鉀、100毫升甲苯及30毫升水之混合物用氮氣吹掃。將溶液加熱回流12小時。冷卻後，將有機層分離，並利用MgSO4
亁燥。藉由管柱層析使用己烷/乙酸乙酯(5%乙酸乙酯)作為溶析液分離出產物。藉由旋轉蒸發去除溶劑，並將產物在真空下蒸發，獲得6克(35.5毫莫耳)2－(鄰－甲苯基)吡啶。
步驟2.將1.5克(8.8毫莫耳)2－(間－甲苯基)吡啶與0.7克(1.45毫莫耳)Ir(acac)3
之混合物利用沙浴加熱至外部溫度為290℃保持12小時。將反應冷卻並溶於二氯甲烷中。將產物亁填塞於矽藻土上並藉由管柱層析使用己烷/二氯甲烷作為溶析液(40%二氯甲烷)分離。收集到0.75克(1.07毫莫耳)產物。
化合物34
步驟1.將3.0克(12.8毫莫耳)5－溴－2－苯基吡啶、2.3克(15.4毫莫耳)2,6－二甲基苯基硼酸、8.6克(38.4毫莫耳)磷酸鉀、0.21克(0.52毫莫耳)2－二環己基膦基－2',6'_二甲氧基聯苯、100毫升甲苯及10毫升水在3頸燒瓶中混合。將系統用氮氮吹掃30分鐘。添加0.12克(0.13毫莫耳)Pd2
(dba)3
並將混合物加熱回流過夜。冷卻至室溫後，藉助矽藻土床過濾反應混合物。利用5%於己烷中之乙酸乙酯將產物進行管柱層析。管柱後獲得3.0克產物(90%產率)。
將3.0克(11.6毫莫耳)5－(2,6－二甲基苯基)－2－苯基吡啶及1.1克(2.3毫莫耳)Ir(acac)3
在30毫升乙二醇中加熱回流42小時。冷卻至室溫後，添加100毫升甲醇。藉由過濾收集沈
澱物。固體係藉由管柱使用1：1二氯甲烷及己烷作為溶析液來純化。獲得1.0克產物。產物藉由於270℃下高真空昇華進一步純化。
化合物35
化合物35之合成：將0.52克(0.64毫莫耳)以上單硼酸酯、0.3克(1.93毫莫耳)苯基硼酸、0.006克(0.0064毫莫耳)叁(二亞苄基丙酮)二鈀(0)[Pd2
(dba)3
]、0.10克(0.025毫莫耳)2－二環己基膦基－2',6'－二甲氧基聯苯(SPhos)及0.4克(1.92毫莫耳)磷酸三鉀(K3
PO4
)稱量於燒瓶中。使用30毫升甲苯及10毫升水作為溶劑並將溶液用氮氣吹掃。將此溶液加熱回流12小時。冷卻後，將有機層分離，並利用MgSO4
亁燥。藉由管柱層析使用己烷/二氯甲烷作為溶析液分離出產物。藉由旋轉蒸發去除溶劑，並將產物在真空下亁燥。藉由於250℃下高真空昇華進一步純化產物，獲得0.3克(0.39毫莫耳)。
化合物36
化合物36之合成：
製備2－溴吡啶(40克，253毫莫耳)、3－溴苯基硼酸(61.0克，303.8毫莫耳)、三苯基膦(6.64克，25.3毫莫耳)、碳酸鉀(87.4克，632.5毫莫耳)於300毫升二甲氧基乙烷及200毫升水中之混合物。使氮氣直接鼓泡至混合物中持續20分鐘，然後添加乙酸鈀(2.84克，12.65毫莫耳)。將反應混合物在氮氣下加熱回流。在結束時，藉由TLC檢測到痕量2－溴吡啶。因此，添加額外10克2－溴苯基硼酸並使反應繼續回流過夜。將反應混合物冷卻並添加水以及乙酸乙酯。將該等層分離，且水層用乙酸乙酯萃取。有機層經硫酸鎂亁燥、過濾並蒸發，得到褐色油狀物。藉由管柱層析利用0至40%乙酸乙酯/己烷溶析、隨後在真空下蒸餾來純化該油狀物。獲得45.1克期望產物(52%產率)，如藉由GC－MS所證實。
製備2－(3－溴苯基)吡啶(12.2克，52.10毫莫耳)、3－(4,4,5,5－四甲基－1,3,2－二氧硼－2－基)苯酚(13.76克，62.53
毫莫耳)、2－二環己基膦基－2',6'－二甲氧基聯苯(856毫克，2.08毫莫耳)、磷酸三鉀單水合物(36克，156.3毫莫耳)於180毫升二噁烷及18毫升水中之混合物。將氮氣直接鼓泡至混合物中持續20分鐘，然後添加叁(二亞苄基丙酮)二鈀(0)(477毫克，0.52毫莫耳)。將反應混合物在氮氣下於100℃下加熱3小時，然後使其冷卻至室溫過夜。將水添加於反應混合物中並將混合物用乙酸乙酯萃取三次。有機萃取物經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用20與40%乙酸乙酯/己烷溶析來純化該殘餘物。獲得12.5克黃色油狀物(97%產率)，如藉由GC－MS所證實。
於0℃下將12.5克(50.6毫莫耳)3'－(吡啶－2－基)聯苯－3－醇、12毫升吡啶、及約200毫升二氯甲烷在500毫升圓底燒瓶中混合。向此混合物中添加14.3克(101.2毫莫耳)三氟乙酸酐並於0℃下攪拌30分鐘，然後於室溫下攪拌1小時。將反應混合物用水洗滌若干次。蒸發溶劑後獲得約19克(約100%產率)三氟甲磺酸酯，如藉由GC－MS所證實。
將8.8克(23.2毫莫耳)三氟甲磺酸3'－(吡啶－2－基)聯苯－3－基酯、4.7克(46毫莫耳)異丁烷硼酸、211毫克Pd2
(dba)3
(0.23毫莫耳)、396毫克(0.965毫莫耳)S－Phos、16.7克(72.6毫莫耳)K3
PO4
H2
O、及300毫升甲苯填充於500毫升圓底燒瓶中。在攪拌的同時將反應混合物在氮氣下最高加熱至回流過夜。藉由二氧化矽凝膠層析利用10%(v/v)於己烷中之乙酸乙酯作為溶析液來純化反應混合物。獲得約5.8克固體(產率87%)產物，如藉由GC－MS所證實。
將3.4克(11.8毫莫耳)2－(3'－異丁基聯苯－3－基)吡啶、2.0克(5.3毫莫耳)IrCl3
.3H2
O、及150毫升溶劑混合物(2乙氧基乙醇/水：3：1)填充於250毫升圓底燒瓶中。將反應混合物在氮氣下最高加熱至回流過夜。使反應混合物冷卻並添加約100毫升甲醇，然後過濾。用甲醇洗滌固體並亁燥。獲得大約3.85克氯橋接之銥二聚體且未經進一步純化即用於下一步驟。
製備2－溴吡啶(8.66克，54.8毫莫耳)、3－甲氧基苯基硼酸
(10克，65.8毫莫耳)、三苯基膦(1.44克，5.48毫莫耳)、碳酸鉀(18.9克，137毫莫耳)於100毫升二甲氧基乙烷及66毫升水中之混合物。將氮氣直接鼓泡至混合物中持續20分鐘，然後添加乙酸鈀(0.61克，2.74毫莫耳)。將反應混合物在氮氣下加熱回流過夜。將反應混合物冷卻並添加水以及乙酸乙酯。將該等層分離，且水層用乙酸乙酯萃取。有機層經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用0至20%乙酸乙酯/己烷溶析來純化該殘餘物。獲得9.7克澄清油狀物(96%產率)，如藉由GC－MS所證實。
製備2－(3－甲氧基苯基)吡啶(9.7克，52.37毫莫耳)及吡啶鹽酸鹽(72.6克，628.44毫莫耳)之混合物。將混合物加熱至220℃。使反應實施2小時。將水添加於冷卻的混合物中且然後用二氯甲烷萃取兩次。有機萃取物經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用0、1、及2%甲醇/二氯甲烷溶析、隨後Kugelrohr蒸餾並自2：1己烷/乙酸乙酯重結晶來純化該殘餘物。獲得5克白色固體(56%產率)，如藉由GC－MS所證實。
製備3－(吡啶－2－基)苯酚(5克，29.21毫莫耳)於100毫升二
氯甲烷中之溶液。向此溶液中添加吡啶(4.7毫升，58.42毫莫耳)並將溶液在冰－鹽浴中冷卻。向此溶液中逐滴添加三氟甲磺酸酐(9.8毫升，58.42毫莫耳)於20毫升二氯甲烷中之溶液。使反應緩慢升溫且2小時後完成。添加水及二氯甲烷並將層分離。用二氯甲烷萃取水層。有機層經硫酸鎂亁燥、過濾及蒸發，得到殘餘物。藉由管柱層析利用5、10及15%乙酸乙酯/己烷溶析來純化該殘餘物。獲得8克澄清液體(90%產率)，如藉由GC－MS所證實。
將3.85克(2.41毫莫耳)上述氯橋接銥二聚體、1.42克(5.3毫莫耳)三氟甲磺酸銀AgOSOCF3
、2.93克(9.64毫莫耳)三氟甲磺酸3－(吡啶－2－基)苯基酯及約300毫升2－乙氧基乙醇在500毫升圓底燒瓶中混合。將混合物在氮氣下最高加熱至回流持續24小時。將反應混合物在二氧化矽凝膠上利用50%於己烷中之二氯甲烷來純化。自該反應混合物分離出約900毫克產物，其包含四配位基雜混銥錯合物。產物係藉由LC－MS來證實。可藉助管柱層析獲得期望部分。
將700毫克(0.647毫莫耳)三氟甲磺酸酯銥錯合物、394毫
克(3.23毫莫耳)苯基硼酸、60毫克Pd2
(dba)3
(0.065毫莫耳)、110毫克(0.268毫莫耳)S－Phos、840毫克(3.65毫莫耳)K3
PO4
.H2
O及50毫升無水甲苯填充於100毫升三頸燒瓶中。將反應混合物氮氣鼓泡30分鐘，然後在氮氣下最高加熱至回流持續20小時。在二氧化矽凝膠管柱上分離反應混合物。獲得610毫克固體(99%產率)，如藉由NMR及LC－MS所證實。
所有裝置皆由高真空(<10－7
托)熱蒸發製作。陽極電極係約1200埃之氧化銦錫(ITO)。陰極係由10埃LiF隨後1,000埃Al構成。製作後立即在氮氣手套箱(<1 ppm H2
O及O2
)中用經環氧樹脂密封之玻璃蓋封裝所有裝置，且在包裝內納入水分吸收劑。
所有裝置實例皆具有有機堆疊，該等有機堆疊自ITO表面開始依次由以下組成：100埃厚的酞菁銅(CuPc)或化合物A作為電洞注入層(HIL)、300埃4,4'－雙[N－(1－萘基)－N－苯基胺基]聯苯(α－NPD)作為電洞傳送層(HTL)、300埃摻雜有6－10 wt%摻雜物發射體(本發明化合物及比較化合物)之4,4'－雙(N－咔唑基)聯苯(CBP)、化合物G或化合物H作為發射層(EML)。電子傳送層(ETL)係由50埃作為ETL2之HTP
及450埃作為ETL1之叁(8－羥基喹啉根基)鋁(Alq3
)、或100埃作為ETL2之化合物H及400埃作為ETL1之Alq3
組成。量測電流－電壓－亮度(IVL)特性、電致發光性質[發射最大值(Emmax
)、半峰全寬(FWHM)及CIE坐標]及運行壽命且匯總於下表1中。對於綠色發光裝置選擇1000 cd/m2
之典型顯示器亮度級用於不同裝置間之比較。對於裝置作業穩定性，所有裝置實例及比較裝置實例皆在40 mA/cm2
之恆定電流密度(J)及室溫下測試。於J＝40 mA/cm2
下於室溫下之初始亮度(L0
)提供於下表1中。
本發明提供其中化合物11或化合物35為該發射摻雜物且化合物H或化合物G為該主體材料之特定裝置。
如本文所用，以下化合物具有以下結構：
亦提供用於OLED發射層之特定發射摻雜物，此可獲得具有尤其佳性能之裝置。特定而言，發射層中使用化合物25或26作為發射摻雜物之裝置如下表1中所示。分別使用化合物25及26作為發射體之裝置展示經改良之裝置穩定性，此表明烷基苯基取代可係有益的。Cmpd.係化合物之縮寫。
5'－苯基上之烷基取代可用於轉變蒸發溫度及穩定性，使發射變窄，且使裝置效率增加。僅具有經取代之2－苯基吡啶中之一的25及26的異配性質使蒸發溫度保持低溫(如表1中所示)，此對於OLED製造很重要，因為需要使該等材料
延長加熱，且低蒸發溫度轉移成較少的熱應力，此通常造成較完全之蒸發。5'－苯基上之烷基取代亦可增加溶解性(如表1中所示)，此在基於溶液方法之裝置製作中很關鍵(如噴墨印刷)。5'烷基苯基亦可使發射變窄，以用於顯示器應用之OLED中較佳，因為可達成更飽和的色彩。此外，使用化合物25及26之裝置證明使用異配錯合物可給予高裝置效率。
同樣地，具有使用異配化合物6、35、11、18或2作為摻雜物之發射層的裝置可導致具有尤其良好的性質之裝置。特定而言，裝置使用化合物6作為摻雜物之發射層、以化合物35作為摻雜物之發射層、以化合物35作為摻雜物且化合物H作為主體材料之發射層、以化合物11作為摻雜物且化合物H作為主體材料之發射層、以化合物18作為摻雜物之發射層、及/或以化合物2作為摻雜物之發射層。該等裝置時常具有一或多項裝置穩定性、發光線寬或裝置效率的改良，如表1中所示。
本發明提供特別的Ir(6－烷基ppy)型化合物，其可導致具有特別窄的發光線寬之裝置。特定而言，裝置使用異配化合物35或11作為發射摻雜物，如表1中所示。據信在6位之取代具有此作用，因為其致力空間效應於Ir錯合物，造成相對較長N－Ir鍵，其轉移成較窄的發射。因此，使Ir(ppy)化合物具有6－烷基且以異配性質特別有用於達成窄發光線寬及經改良之裝置穩定性，而與均配對應物相比未顯著增加蒸發溫度。
表1係裝置數據的匯總。比較實例1及裝置實例1－2具有相同裝置結構，只是比較實例1使用Ir(ppy)3
作為發射體，而裝置實例1－3分別使用化合物25及26作為發射體。化合物25在5'位具有異丁基苯基及化合物26在5'位具有甲基苯基。比較實例1及裝置實例1－2分別具有59、83及90小時之T80%
(其定義為初始亮度L0
下降至其初始亮度的80%所花費的時間)。該結果表明，烷基苯基取代可助益於裝置穩定性，如美國專利第20050119485A1號中所假定。然而，僅具有經取代之2－苯基吡啶中之一的化合物25及26的異配性質使蒸發溫度保持低溫，僅比Ir(ppy)3
高數℃。低蒸發溫度對於OLED製造很重要，因為需要使該等材料延長加熱，且低蒸發溫度轉移成較少的熱應力，此通常造成較完全之蒸發。5'－苯基上之烷基取代可進一步用於轉變蒸發溫度及溶解性。在基於溶液方法之裝置製作中(如噴墨印刷)，具有高溶解性很關鍵。該結果亦顯示5'－烷基苯基亦可使發射變窄。比較實例1具有74奈米之FWHM，而裝置實例1及2分別具有68及70奈米之FWHM。因為可達成更飽和色彩，故窄發射以用於顯示器應用之OLED中較佳。此外，比較實例1及裝置實例1及2在1000 cd/m2
下分別具有50、56及59 cd/A之裝置效率。此表明使用異配錯合物可給予高裝置效率。
基於結構相似之配位基的更多均配及異配之比較可發現於表1中。比較實例2(具有均配化合物B)及裝置實例4(具有異配化合物3)分別具有63及47小時之T80%
。FWHM皆為74
奈米且裝置效率皆為約60 cd/A。在此情況下，異配性質並不提供助益。比較實例3(具有均配化合物C，揭示於WO06014599A2中)及裝置實例5(具有異配化合物6)分別具有12及46小時之T80%
。FWHM皆為72奈米，且裝置效率分別為41及59 cd/A。在此情況下，該異配性質提供助益於裝置穩定性及效率。比較實例4(具有均配化合物D，揭示於WO06014599A2中)、裝置實例6(具有異配化合物35)、裝置實例7(具有異配化合物35及化合物H作為主體材料)及裝置實例8(具有異配化合物11及化合物H作為主體材料)分別具有14、18、85及38小時之T80%
。FWHM分別為68、68、69及66奈米，且裝置效率分別為44、56、52及48cd/A。在此情況下，該異配性質提供助益於裝置穩定性。比較實例9(具有均配化合物17)及裝置實例10(具有異配化合物18)分別具有7及3小時之T80%
。FWHM分別為74及71奈米，且裝置效率分別為約23及27 cd/A。在此情況下，該異配性質提供助益於發光線寬及裝置效率。比較實例11(具有均配化合物1)及裝置實例12(具有異配化合物2)皆具有4小時之T80%
。FWHM分別為76及74奈米，且裝置效率分別為約35及44 cd/A。在此情況下，該異配性質提供助益於發光線寬及裝置效率。總結裝置結果，基於使用異配類似物作為摻雜物發射體之裝置，時常有一或多項裝置穩定性、發光線寬或裝置效率的改良。
Ir(6－烷基ppy)型錯合物具有尤其窄的發光線寬。裝置實例6、7及8之FWHM分別為68、69及66奈米。據信在6位之
取代具有此作用，因為其致力空間效應於Ir錯合物，造成相對較長N－Ir鍵，其轉移成較窄的發射。因此，使Ir(ppy)錯合物具有6－烷基且以異配性質特別有用於達成窄發光線寬及經改良之裝置穩定性，而與均配對應物相比未顯著增加蒸發溫度。
如自表1中所看出，主體材料及ETL2材料在影響裝置性能及壽命方面亦很重要。舉例而言，裝置實例6使用化合物35作為發射體、CBP作為主體材料且HTP作為ETL2，裝置實例7使用化合物35作為發射體、化合物H作為主體材料且化合物H作為ETL2，且裝置實例16使用化合物35作為發射體、化合物G作為主體材料且化合物H作為ETL2。效率分別為56、52及56 cd/A。T80%
在約L0
＝15000 cd/m2
下分別為18、85及210小時。FWHM分別為68、69及70奈米。CIE分別為(0.317,0.625)、(0.316,0.625)及(0.313,0.625)。儘管效率、FWHM及CIE相似，但具有化合物H及化合物G作為主體材料之裝置具有經改良壽命，其與具有CBP作為主體材料之裝置相比分別增加約5及12倍。同樣地，裝置實例8使用化合物11作為發射體、化合物H作為主體材料且化合物H作為ETL2，且裝置實例17使用化合物11作為發射體、化合物G作為主體材料且化合物H作為ETL2。效率分別為48及56 cd/A。T80%
分別為在L0
＝13000 cd/m2
下38小時及在L0
＝16000 cd/m2
下117小時。FWHM分別為66及65奈米。CIE分別為(0.298,0.626)及(0.290,0.630)。在此情況下，使用化合物G作為主體材料使效率及CIE略有改良，
且與化合物H作為主體材料具有之裝置相比使裝置壽命改良至少3倍。基於作為磷光OLED主體材料之聯伸三苯化合物(美國申請案第61/017,506號)的化合物H作為主體材料可優於咔唑。此外，基於作為磷光OLED主體材料之二苯并噻吩化合物(美國申請案第61/017,480號)的化合物G作為主體材料可係有利地。使用聯伸三苯主體材料及聯伸三苯ETL2組合可尤其有利。使用二苯并噻吩主體材料及聯伸三苯ETL2組合可甚至更有利。
可能難以藉由配位基與Ir(acac)3
之直接錯合合成具有6－烷基之Irppy錯合物。舉例而言，WO 2006/014599A2中報導在化合物11之製備中中間體I之合成。配位基與Ir(acac)3
之直接錯合僅獲得5.4%的中間體I。然而，在化合物11之製備中，藉助Ir(L)2 t
Buacac合成中間體I。最後步驟之產率明顯較佳(74%)。同樣地，化合物17及化合物32係藉助Ir(L)2 t
Buacac途徑以與直接錯合方法相比經改良之產率來合成。不欲受限於理論，據信t
Buacac配位基係比acac配位基好的離去基團，此使得在叁Ir錯合物形成中更易於被第三配位基置換。此方法提供用於OLED中具有光活性空間需求之環金屬化配位基的叁錯合物的高產率合成。
應瞭解，本文所述之各種實施例僅用於舉例說明，且其不欲限制本發明之範圍。舉例而言，許多本文所述材料及結構可由其他材料及結構代替，此並不背離本發明之精神。因此，所申請之本發明可包括本文所述特定實例及較佳實施例之變體，如熟悉該項技術者將顯而易見。應瞭
解，關於本發明為何可行之各種理論不欲具有限制性。
100‧‧‧有機發光裝置
110‧‧‧基板
115‧‧‧陽極
120‧‧‧電洞注入層
125‧‧‧電洞傳送層
130‧‧‧電子阻擋層
135‧‧‧發射層
140‧‧‧電洞阻擋層
145‧‧‧電子傳送層
150‧‧‧電子注入層
155‧‧‧保護層
160‧‧‧陰極
162‧‧‧第一導電層
164‧‧‧第二導電層
200‧‧‧倒置OLED
210‧‧‧基板
215‧‧‧陰極
220‧‧‧發射層
22電洞傳送層
230‧‧‧陽極
圖1展示有機發光裝置。
圖2顯示不具有單獨的電子傳送層之倒置有機發光裝置。
圖3展示銥錯合物。
圖4展示合成途徑中之反應。
(無元件符號說明)
Claims (17)
- 一種具有下式之異配銥化合物，
- 如請求項1之化合物，其中該化合物係選自由以下組成之群：
- 一種有機發光裝置，其包含：陽極；陰極；及有機發射層，其佈置於該陽極與該陰極之間，該有機層包含具有下式之化合物：
- 如請求項3之裝置，其中該化合物係選自由以下組成之群：
- 如請求項3之裝置，其中該有機發射層進一步包含主體材料。
- 如請求項5之裝置，其中該主體材料係包含咔唑基團、聯伸三苯基團或二苯并噻吩基團之化合物。
- 如請求項3之裝置，其中該化合物係：
- 如請求項7之裝置，其中該有機發射層包含主體材料及發射摻雜物，且該化合物11係該發射摻雜物。
- 如請求項7之裝置，其中該化合物11係發射摻雜物，且化合物H： 係主體材料。
- 如請求項7之裝置，其中該化合物11係發射摻雜物，且化合物G： 係主體材料。
- 如請求項3之裝置，其中該化合物係：
- 如請求項11之裝置，其中該有機發射層包含主體材料及發射摻雜物，且該化合物35係該發射摻雜物。
- 如請求項11之裝置，其中該化合物35係發射摻雜物，且化合物H： 係主體材料。
- 如請求項11之裝置，其中該化合物35係發射摻雜物，且化合物G： 係主體材料。
- 一種有機發光裝置，其包含：陽極；陰極；及有機發射層，其佈置於該陽極與該陰極之間，該有機層包含具有下式之化合物：
- 一種有機發光裝置，其包含：陽極；陰極；及有機發射層，其佈置於該陽極與該陰極之間，該有機層包含具有下式之化合物：
- 一種有機發光裝置，其包含：陽極；陰極；及有機發射層，其佈置於該陽極與該陰極之間，該有機層包含具有下式之化合物：
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Families Citing this family (699)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9070884B2 (en) | 2005-04-13 | 2015-06-30 | Universal Display Corporation | Hybrid OLED having phosphorescent and fluorescent emitters |
| US8586204B2 (en) | 2007-12-28 | 2013-11-19 | Universal Display Corporation | Phosphorescent emitters and host materials with improved stability |
| US8007927B2 (en) | 2007-12-28 | 2011-08-30 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
| US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
| ATE553111T1 (de) | 2006-02-10 | 2012-04-15 | Universal Display Corp | Metallkomplexe aus imidazoä1,2-füphenanthridin- liganden und deren verwendung in oled vorrichtungen |
| KR101634508B1 (ko) | 2007-03-08 | 2016-06-28 | 유니버셜 디스플레이 코포레이션 | 인광성 물질 |
| US9130177B2 (en) | 2011-01-13 | 2015-09-08 | Universal Display Corporation | 5-substituted 2 phenylquinoline complexes materials for light emitting diode |
| US20130032785A1 (en) | 2011-08-01 | 2013-02-07 | Universal Display Corporation | Materials for organic light emitting diode |
| KR101565724B1 (ko) | 2007-08-08 | 2015-11-03 | 유니버셜 디스플레이 코포레이션 | 트리페닐렌기를 포함하는 벤조 융합 티오펜 또는 벤조 융합 푸란 화합물 |
| CN103601609B (zh) | 2007-08-08 | 2017-07-28 | 通用显示公司 | 在磷光性发光二极管中的单苯并[9，10]菲生色团 |
| WO2009073245A1 (en) | 2007-12-06 | 2009-06-11 | Universal Display Corporation | Light-emitting organometallic complexes |
| JP5591800B2 (ja) | 2008-06-30 | 2014-09-17 | ユニバーサル・ディスプレイ・コーポレーション | トリフェニレンを含有するホール輸送材料 |
| WO2010027583A1 (en) | 2008-09-03 | 2010-03-11 | Universal Display Corporation | Phosphorescent materials |
| US9034483B2 (en) | 2008-09-16 | 2015-05-19 | Universal Display Corporation | Phosphorescent materials |
| EP3185333B1 (en) | 2008-09-25 | 2023-09-06 | Universal Display Corporation | Organoselenium materials and their uses in organic light emitting devices |
| JP5854839B2 (ja) * | 2008-11-11 | 2016-02-09 | ユニバーサル ディスプレイ コーポレイション | 燐光発光体 |
| US8815415B2 (en) | 2008-12-12 | 2014-08-26 | Universal Display Corporation | Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes |
| US9067947B2 (en) | 2009-01-16 | 2015-06-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US8709615B2 (en) | 2011-07-28 | 2014-04-29 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
| US8722205B2 (en) | 2009-03-23 | 2014-05-13 | Universal Display Corporation | Heteroleptic iridium complex |
| US11910700B2 (en) | 2009-03-23 | 2024-02-20 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
| TWI638807B (zh) | 2009-04-28 | 2018-10-21 | 環球展覽公司 | 具有甲基-ｄ３取代之銥錯合物 |
| US8586203B2 (en) | 2009-05-20 | 2013-11-19 | Universal Display Corporation | Metal complexes with boron-nitrogen heterocycle containing ligands |
| JP4500364B1 (ja) * | 2009-08-31 | 2010-07-14 | 富士フイルム株式会社 | 有機電界発光素子 |
| JP4542607B1 (ja) | 2009-08-31 | 2010-09-15 | 富士フイルム株式会社 | イリジウム錯体を昇華精製する方法、及び有機電界発光素子の製造方法 |
| JP4564584B1 (ja) * | 2009-08-31 | 2010-10-20 | 富士フイルム株式会社 | 有機電界発光素子 |
| JP5457907B2 (ja) | 2009-08-31 | 2014-04-02 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
| DE102009041414A1 (de) * | 2009-09-16 | 2011-03-17 | Merck Patent Gmbh | Metallkomplexe |
| US8545996B2 (en) | 2009-11-02 | 2013-10-01 | The University Of Southern California | Ion-pairing soft salts based on organometallic complexes and their applications in organic light emitting diodes |
| US8580394B2 (en) | 2009-11-19 | 2013-11-12 | Universal Display Corporation | 3-coordinate copper(I)-carbene complexes |
| US8288187B2 (en) | 2010-01-20 | 2012-10-16 | Universal Display Corporation | Electroluminescent devices for lighting applications |
| US9156870B2 (en) * | 2010-02-25 | 2015-10-13 | Universal Display Corporation | Phosphorescent emitters |
| US9175211B2 (en) * | 2010-03-03 | 2015-11-03 | Universal Display Corporation | Phosphorescent materials |
| JP5833322B2 (ja) | 2010-03-12 | 2015-12-16 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子及びその製造方法 |
| US8963132B2 (en) | 2010-03-25 | 2015-02-24 | Universal Display Corporation | Solution processable doped triarylamine hole injection materials |
| US8968887B2 (en) | 2010-04-28 | 2015-03-03 | Universal Display Corporation | Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings |
| CN103026521B (zh) | 2010-04-28 | 2016-11-09 | 通用显示公司 | 沉积预混合的材料 |
| US8673458B2 (en) | 2010-06-11 | 2014-03-18 | Universal Display Corporation | Delayed fluorescence OLED |
| US8742657B2 (en) | 2010-06-11 | 2014-06-03 | Universal Display Corporation | Triplet-Triplet annihilation up conversion (TTA-UC) for display and lighting applications |
| JP4751955B1 (ja) * | 2010-07-09 | 2011-08-17 | 富士フイルム株式会社 | 有機電界発光素子 |
| WO2012016074A1 (en) | 2010-07-29 | 2012-02-02 | University Of Southern California | Co-deposition methods for the fabrication of organic optoelectronic devices |
| JP5763309B2 (ja) * | 2010-07-30 | 2015-08-12 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子及び化合物 |
| US9954180B2 (en) | 2010-08-20 | 2018-04-24 | Universal Display Corporation | Bicarbazole compounds for OLEDs |
| JP5847420B2 (ja) | 2010-09-08 | 2016-01-20 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子及び化合物 |
| US8932734B2 (en) | 2010-10-08 | 2015-01-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US8269317B2 (en) | 2010-11-11 | 2012-09-18 | Universal Display Corporation | Phosphorescent materials |
| US20120138906A1 (en) | 2010-12-07 | 2012-06-07 | The University of Southern California USC Stevens Institute for Innovation | Capture agents for unsaturated metal complexes |
| US10008677B2 (en) | 2011-01-13 | 2018-06-26 | Universal Display Corporation | Materials for organic light emitting diode |
| US8415031B2 (en) | 2011-01-24 | 2013-04-09 | Universal Display Corporation | Electron transporting compounds |
| US20130306962A1 (en) * | 2011-02-11 | 2013-11-21 | Universal Display Corporation | Organic light emitting device and materials for use in same |
| US8563737B2 (en) | 2011-02-23 | 2013-10-22 | Universal Display Corporation | Methods of making bis-tridentate carbene complexes of ruthenium and osmium |
| US8748011B2 (en) | 2011-02-23 | 2014-06-10 | Universal Display Corporation | Ruthenium carbene complexes for OLED material |
| JP6042352B2 (ja) | 2011-02-23 | 2016-12-14 | ユニバーサル ディスプレイ コーポレイション | 新規四座配位白金錯体 |
| US9005772B2 (en) | 2011-02-23 | 2015-04-14 | Universal Display Corporation | Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials |
| US8492006B2 (en) | 2011-02-24 | 2013-07-23 | Universal Display Corporation | Germanium-containing red emitter materials for organic light emitting diode |
| EP2551949A1 (en) * | 2011-07-28 | 2013-01-30 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Metal complexes for use as dopants and other uses |
| US8883322B2 (en) | 2011-03-08 | 2014-11-11 | Universal Display Corporation | Pyridyl carbene phosphorescent emitters |
| JP5984450B2 (ja) | 2011-03-31 | 2016-09-06 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子、並びに、該素子を用いた発光装置、表示装置、照明装置及び該素子用の化合物 |
| US8580399B2 (en) | 2011-04-08 | 2013-11-12 | Universal Display Corporation | Substituted oligoazacarbazoles for light emitting diodes |
| US8927308B2 (en) | 2011-05-12 | 2015-01-06 | Universal Display Corporation | Method of forming bus line designs for large-area OLED lighting |
| US8432095B2 (en) | 2011-05-11 | 2013-04-30 | Universal Display Corporation | Process for fabricating metal bus lines for OLED lighting panels |
| US8564192B2 (en) | 2011-05-11 | 2013-10-22 | Universal Display Corporation | Process for fabricating OLED lighting panels |
| US9212197B2 (en) | 2011-05-19 | 2015-12-15 | Universal Display Corporation | Phosphorescent heteroleptic phenylbenzimidazole dopants |
| US8795850B2 (en) | 2011-05-19 | 2014-08-05 | Universal Display Corporation | Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology |
| US8748012B2 (en) | 2011-05-25 | 2014-06-10 | Universal Display Corporation | Host materials for OLED |
| US10158089B2 (en) * | 2011-05-27 | 2018-12-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10079349B2 (en) * | 2011-05-27 | 2018-09-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2012170463A1 (en) | 2011-06-08 | 2012-12-13 | Universal Display Corporation | Heteroleptic iridium carbene complexes and light emitting device using them |
| US8659036B2 (en) | 2011-06-17 | 2014-02-25 | Universal Display Corporation | Fine tuning of emission spectra by combination of multiple emitter spectra |
| US8884316B2 (en) | 2011-06-17 | 2014-11-11 | Universal Display Corporation | Non-common capping layer on an organic device |
| KR101965014B1 (ko) | 2011-07-14 | 2019-04-02 | 유니버셜 디스플레이 코포레이션 | Ｏｌｅｄ에서 무기 호스트 |
| US9023420B2 (en) | 2011-07-14 | 2015-05-05 | Universal Display Corporation | Composite organic/inorganic layer for organic light-emitting devices |
| US9397310B2 (en) | 2011-07-14 | 2016-07-19 | Universal Display Corporation | Organice electroluminescent materials and devices |
| US9783564B2 (en) | 2011-07-25 | 2017-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US8409729B2 (en) | 2011-07-28 | 2013-04-02 | Universal Display Corporation | Host materials for phosphorescent OLEDs |
| US8926119B2 (en) | 2011-08-04 | 2015-01-06 | Universal Display Corporation | Extendable light source with variable light emitting area |
| US8552420B2 (en) | 2011-08-09 | 2013-10-08 | Universal Display Corporation | OLED light panel with controlled brightness variation |
| US9493698B2 (en) | 2011-08-31 | 2016-11-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP2762483A1 (en) | 2011-09-12 | 2014-08-06 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element material having silicon-containing four membered ring structure, and organic electroluminescent element |
| CN103797602B (zh) | 2011-09-12 | 2016-03-23 | 新日铁住金化学株式会社 | 有机电致发光元件 |
| CN103907217B (zh) | 2011-09-12 | 2016-10-12 | 新日铁住金化学株式会社 | 有机电致发光元件 |
| US10340471B2 (en) * | 2011-09-30 | 2019-07-02 | Udc Ireland Limited | Organic electroluminescent element and novel iridium complex |
| US8652656B2 (en) | 2011-11-14 | 2014-02-18 | Universal Display Corporation | Triphenylene silane hosts |
| US9193745B2 (en) | 2011-11-15 | 2015-11-24 | Universal Display Corporation | Heteroleptic iridium complex |
| JP2013103918A (ja) | 2011-11-15 | 2013-05-30 | Udc Ireland Ltd | 電荷輸送材料、有機電界発光素子及び該素子を用いたことを特徴とする発光装置、表示装置または照明装置 |
| US9217004B2 (en) | 2011-11-21 | 2015-12-22 | Universal Display Corporation | Organic light emitting materials |
| US9512355B2 (en) | 2011-12-09 | 2016-12-06 | Universal Display Corporation | Organic light emitting materials |
| KR101965292B1 (ko) | 2011-12-12 | 2019-04-04 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기전계발광 소자용 재료 및 그것을 사용한 유기전계발광 소자 |
| US20130146875A1 (en) | 2011-12-13 | 2013-06-13 | Universal Display Corporation | Split electrode for organic devices |
| TWI523845B (zh) | 2011-12-23 | 2016-03-01 | 半導體能源研究所股份有限公司 | 有機金屬錯合物，發光元件，發光裝置，電子裝置及照明裝置 |
| CN104136449A (zh) | 2011-12-28 | 2014-11-05 | 索尔维公司 | 杂配体金属络合物的制备 |
| EP2676964A1 (en) | 2012-06-18 | 2013-12-25 | Solvay Sa | Preparation of heteroleptic metal complexes |
| US8987451B2 (en) | 2012-01-03 | 2015-03-24 | Universal Display Corporation | Synthesis of cyclometallated platinum(II) complexes |
| US9461254B2 (en) | 2012-01-03 | 2016-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9163174B2 (en) | 2012-01-04 | 2015-10-20 | Universal Display Corporation | Highly efficient phosphorescent materials |
| KR102012047B1 (ko) | 2012-01-06 | 2019-08-19 | 유니버셜 디스플레이 코포레이션 | 효율이 큰 인광 물질 |
| US8969592B2 (en) | 2012-01-10 | 2015-03-03 | Universal Display Corporation | Heterocyclic host materials |
| US10211413B2 (en) | 2012-01-17 | 2019-02-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP5978843B2 (ja) | 2012-02-02 | 2016-08-24 | コニカミノルタ株式会社 | イリジウム錯体化合物、有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
| US9118017B2 (en) | 2012-02-27 | 2015-08-25 | Universal Display Corporation | Host compounds for red phosphorescent OLEDs |
| EP2827397B1 (en) | 2012-03-12 | 2019-04-03 | NIPPON STEEL Chemical & Material Co., Ltd. | Organic electroluminescent element |
| US9386657B2 (en) | 2012-03-15 | 2016-07-05 | Universal Display Corporation | Organic Electroluminescent materials and devices |
| US9054323B2 (en) | 2012-03-15 | 2015-06-09 | Universal Display Corporation | Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds |
| US8723209B2 (en) | 2012-04-27 | 2014-05-13 | Universal Display Corporation | Out coupling layer containing particle polymer composite |
| US9184399B2 (en) | 2012-05-04 | 2015-11-10 | Universal Display Corporation | Asymmetric hosts with triaryl silane side chains |
| US9773985B2 (en) | 2012-05-21 | 2017-09-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9670404B2 (en) | 2012-06-06 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2013187894A1 (en) * | 2012-06-14 | 2013-12-19 | Universal Display Corporation | Biscarbazole derivative host materials and red emitter for oled emissive region |
| US9502672B2 (en) | 2012-06-21 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102014888B1 (ko) | 2012-06-28 | 2019-08-27 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계발광 소자용 재료 및 유기 전계발광 소자 |
| US9725476B2 (en) * | 2012-07-09 | 2017-08-08 | Universal Display Corporation | Silylated metal complexes |
| US9231218B2 (en) | 2012-07-10 | 2016-01-05 | Universal Display Corporation | Phosphorescent emitters containing dibenzo[1,4]azaborinine structure |
| US9059412B2 (en) | 2012-07-19 | 2015-06-16 | Universal Display Corporation | Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs |
| US9540329B2 (en) * | 2012-07-19 | 2017-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2014013936A1 (ja) | 2012-07-19 | 2014-01-23 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
| US9663544B2 (en) | 2012-07-25 | 2017-05-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9318710B2 (en) | 2012-07-30 | 2016-04-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| TWI587557B (zh) * | 2012-08-03 | 2017-06-11 | 半導體能源研究所股份有限公司 | 發光元件、發光裝置、顯示裝置、電子裝置及照明設備 |
| JP6217642B2 (ja) | 2012-08-24 | 2017-10-25 | コニカミノルタ株式会社 | 透明電極、電子デバイス、および透明電極の製造方法 |
| US9978958B2 (en) | 2012-08-24 | 2018-05-22 | Universal Display Corporation | Phosphorescent emitters with phenylimidazole ligands |
| US8952362B2 (en) | 2012-08-31 | 2015-02-10 | The Regents Of The University Of Michigan | High efficiency and brightness fluorescent organic light emitting diode by triplet-triplet fusion |
| US10957870B2 (en) | 2012-09-07 | 2021-03-23 | Universal Display Corporation | Organic light emitting device |
| CN107573363A (zh) | 2012-09-20 | 2018-01-12 | Udc 爱尔兰有限责任公司 | 供电子应用的氮杂二苯并呋喃和包含氮杂二苯并呋喃的电子器件 |
| US9287513B2 (en) | 2012-09-24 | 2016-03-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9312505B2 (en) | 2012-09-25 | 2016-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| TWI599570B (zh) | 2012-09-28 | 2017-09-21 | 新日鐵住金化學股份有限公司 | Compounds for organic electroluminescent devices and organic electroluminescent devices |
| US9252363B2 (en) | 2012-10-04 | 2016-02-02 | Universal Display Corporation | Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers |
| US8692241B1 (en) | 2012-11-08 | 2014-04-08 | Universal Display Corporation | Transition metal complexes containing triazole and tetrazole carbene ligands |
| US9634264B2 (en) | 2012-11-09 | 2017-04-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US8946697B1 (en) | 2012-11-09 | 2015-02-03 | Universal Display Corporation | Iridium complexes with aza-benzo fused ligands |
| US9748500B2 (en) | 2015-01-15 | 2017-08-29 | Universal Display Corporation | Organic light emitting materials |
| US9685617B2 (en) | 2012-11-09 | 2017-06-20 | Universal Display Corporation | Organic electronuminescent materials and devices |
| US10069090B2 (en) | 2012-11-20 | 2018-09-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9190623B2 (en) | 2012-11-20 | 2015-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9512136B2 (en) | 2012-11-26 | 2016-12-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9166175B2 (en) | 2012-11-27 | 2015-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9196860B2 (en) | 2012-12-04 | 2015-11-24 | Universal Display Corporation | Compounds for triplet-triplet annihilation upconversion |
| US8716484B1 (en) | 2012-12-05 | 2014-05-06 | Universal Display Corporation | Hole transporting materials with twisted aryl groups |
| US9209411B2 (en) | 2012-12-07 | 2015-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9653691B2 (en) | 2012-12-12 | 2017-05-16 | Universal Display Corporation | Phosphorescence-sensitizing fluorescence material system |
| KR102160720B1 (ko) | 2012-12-17 | 2020-09-28 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계발광 소자 |
| US10400163B2 (en) | 2013-02-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10367154B2 (en) | 2013-02-21 | 2019-07-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US8927749B2 (en) | 2013-03-07 | 2015-01-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9419225B2 (en) | 2013-03-14 | 2016-08-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9997712B2 (en) | 2013-03-27 | 2018-06-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP6350518B2 (ja) | 2013-03-29 | 2018-07-04 | 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、それを具備した照明装置及び表示装置 |
| EP2983222A4 (en) | 2013-03-29 | 2016-09-28 | Konica Minolta Inc | MATERIAL FOR ORGANIC ELECTROLUMINESCENE ELEMENTS, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE |
| US9537106B2 (en) | 2013-05-09 | 2017-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9735373B2 (en) | 2013-06-10 | 2017-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2014204464A1 (en) * | 2013-06-20 | 2014-12-24 | Universal Display Corporation | Phosphorescent organic light emitting devices having a hole-transporting host in the emissive region |
| US9673401B2 (en) | 2013-06-28 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10199581B2 (en) | 2013-07-01 | 2019-02-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10121975B2 (en) | 2013-07-03 | 2018-11-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9761807B2 (en) | 2013-07-15 | 2017-09-12 | Universal Display Corporation | Organic light emitting diode materials |
| US9324949B2 (en) | 2013-07-16 | 2016-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9553274B2 (en) | 2013-07-16 | 2017-01-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9224958B2 (en) | 2013-07-19 | 2015-12-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20150028290A1 (en) | 2013-07-25 | 2015-01-29 | Universal Display Corporation | Heteroleptic osmium complex and method of making the same |
| US9831437B2 (en) | 2013-08-20 | 2017-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10074806B2 (en) | 2013-08-20 | 2018-09-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9932359B2 (en) | 2013-08-30 | 2018-04-03 | University Of Southern California | Organic electroluminescent materials and devices |
| US10199582B2 (en) | 2013-09-03 | 2019-02-05 | University Of Southern California | Organic electroluminescent materials and devices |
| US9735378B2 (en) | 2013-09-09 | 2017-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9748503B2 (en) | 2013-09-13 | 2017-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10003034B2 (en) | 2013-09-30 | 2018-06-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9831447B2 (en) | 2013-10-08 | 2017-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9293712B2 (en) | 2013-10-11 | 2016-03-22 | Universal Display Corporation | Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same |
| US9853229B2 (en) | 2013-10-23 | 2017-12-26 | University Of Southern California | Organic electroluminescent materials and devices |
| US20150115250A1 (en) | 2013-10-29 | 2015-04-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2015063046A1 (en) | 2013-10-31 | 2015-05-07 | Basf Se | Azadibenzothiophenes for electronic applications |
| US9306179B2 (en) | 2013-11-08 | 2016-04-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9647218B2 (en) | 2013-11-14 | 2017-05-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9905784B2 (en) | 2013-11-15 | 2018-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10056565B2 (en) | 2013-11-20 | 2018-08-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10644251B2 (en) | 2013-12-04 | 2020-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9876173B2 (en) | 2013-12-09 | 2018-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10355227B2 (en) | 2013-12-16 | 2019-07-16 | Universal Display Corporation | Metal complex for phosphorescent OLED |
| US9847496B2 (en) | 2013-12-23 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10135008B2 (en) | 2014-01-07 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9978961B2 (en) | 2014-01-08 | 2018-05-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9755159B2 (en) | 2014-01-23 | 2017-09-05 | Universal Display Corporation | Organic materials for OLEDs |
| US9935277B2 (en) | 2014-01-30 | 2018-04-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP2015151426A (ja) | 2014-02-12 | 2015-08-24 | セイコーエプソン株式会社 | 刺激応答性ゲル材料 |
| JP2015151427A (ja) * | 2014-02-12 | 2015-08-24 | セイコーエプソン株式会社 | 刺激応答性ゲル材料および刺激応答性ゲル材料の製造方法 |
| JP2015151436A (ja) | 2014-02-13 | 2015-08-24 | セイコーエプソン株式会社 | 刺激応答性ゲル材料 |
| US9590194B2 (en) | 2014-02-14 | 2017-03-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9847497B2 (en) | 2014-02-18 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10003033B2 (en) * | 2014-02-18 | 2018-06-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10707423B2 (en) | 2014-02-21 | 2020-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9647217B2 (en) | 2014-02-24 | 2017-05-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9502656B2 (en) | 2014-02-24 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10403825B2 (en) | 2014-02-27 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9673407B2 (en) | 2014-02-28 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9181270B2 (en) | 2014-02-28 | 2015-11-10 | Universal Display Corporation | Method of making sulfide compounds |
| US9590195B2 (en) | 2014-02-28 | 2017-03-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9190620B2 (en) | 2014-03-01 | 2015-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9397309B2 (en) | 2014-03-13 | 2016-07-19 | Universal Display Corporation | Organic electroluminescent devices |
| US10208026B2 (en) | 2014-03-18 | 2019-02-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9748504B2 (en) | 2014-03-25 | 2017-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9929353B2 (en) | 2014-04-02 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9691993B2 (en) | 2014-04-09 | 2017-06-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10008679B2 (en) | 2014-04-14 | 2018-06-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9847498B2 (en) | 2014-04-14 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10256427B2 (en) | 2014-04-15 | 2019-04-09 | Universal Display Corporation | Efficient organic electroluminescent devices |
| US9450198B2 (en) | 2014-04-15 | 2016-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9741941B2 (en) | 2014-04-29 | 2017-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10457699B2 (en) | 2014-05-02 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP6759108B2 (ja) | 2014-05-08 | 2020-09-23 | ユニバーサル ディスプレイ コーポレイション | 安定化されたイミダゾフェナントリジン材料 |
| US10636983B2 (en) | 2014-05-08 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10301338B2 (en) | 2014-05-08 | 2019-05-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10403830B2 (en) | 2014-05-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9997716B2 (en) | 2014-05-27 | 2018-06-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10461260B2 (en) | 2014-06-03 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102308903B1 (ko) * | 2014-06-17 | 2021-10-06 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US9911931B2 (en) | 2014-06-26 | 2018-03-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10297762B2 (en) | 2014-07-09 | 2019-05-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10566546B2 (en) | 2014-07-14 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9929357B2 (en) | 2014-07-22 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2016016791A1 (en) | 2014-07-28 | 2016-02-04 | Idemitsu Kosan Co., Ltd (Ikc) | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
| KR102241847B1 (ko) * | 2014-07-29 | 2021-04-20 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US11108000B2 (en) | 2014-08-07 | 2021-08-31 | Unniversal Display Corporation | Organic electroluminescent materials and devices |
| US10411200B2 (en) | 2014-08-07 | 2019-09-10 | Universal Display Corporation | Electroluminescent (2-phenylpyridine)iridium complexes and devices |
| EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
| KR101646732B1 (ko) * | 2014-08-08 | 2016-08-08 | 서울대학교산학협력단 | 유기 발광 소자 |
| EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
| US10749113B2 (en) | 2014-09-29 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10043987B2 (en) | 2014-09-29 | 2018-08-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10135007B2 (en) | 2014-09-29 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10361375B2 (en) | 2014-10-06 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9397302B2 (en) | 2014-10-08 | 2016-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10854826B2 (en) | 2014-10-08 | 2020-12-01 | Universal Display Corporation | Organic electroluminescent compounds, compositions and devices |
| US10950803B2 (en) | 2014-10-13 | 2021-03-16 | Universal Display Corporation | Compounds and uses in devices |
| KR102417121B1 (ko) * | 2014-10-17 | 2022-07-06 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| KR102527225B1 (ko) * | 2014-10-17 | 2023-05-03 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| KR102577004B1 (ko) * | 2014-10-17 | 2023-09-13 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US9484541B2 (en) | 2014-10-20 | 2016-11-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP3015469B1 (en) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications |
| US10868261B2 (en) * | 2014-11-10 | 2020-12-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10411201B2 (en) | 2014-11-12 | 2019-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10038151B2 (en) | 2014-11-12 | 2018-07-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9882151B2 (en) | 2014-11-14 | 2018-01-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9871212B2 (en) | 2014-11-14 | 2018-01-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
| US9761814B2 (en) | 2014-11-18 | 2017-09-12 | Universal Display Corporation | Organic light-emitting materials and devices |
| US10381569B2 (en) | 2014-11-25 | 2019-08-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9444075B2 (en) | 2014-11-26 | 2016-09-13 | Universal Display Corporation | Emissive display with photo-switchable polarization |
| EP3034507A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs) |
| EP3034506A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-functionalized carbazole derivatives for electronic applications |
| US9450195B2 (en) | 2014-12-17 | 2016-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102344883B1 (ko) | 2014-12-17 | 2021-12-29 | 삼성전자주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
| US10253252B2 (en) | 2014-12-30 | 2019-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10636978B2 (en) | 2014-12-30 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9312499B1 (en) | 2015-01-05 | 2016-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9406892B2 (en) | 2015-01-07 | 2016-08-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9711730B2 (en) | 2015-01-25 | 2017-07-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10418569B2 (en) | 2015-01-25 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10355222B2 (en) | 2015-02-06 | 2019-07-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10644247B2 (en) | 2015-02-06 | 2020-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10418562B2 (en) | 2015-02-06 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP3054498B1 (en) | 2015-02-06 | 2017-09-20 | Idemitsu Kosan Co., Ltd. | Bisimidazodiazocines |
| EP3053918B1 (en) | 2015-02-06 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | 2-carbazole substituted benzimidazoles for electronic applications |
| US10177316B2 (en) | 2015-02-09 | 2019-01-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10103339B2 (en) | 2015-02-11 | 2018-10-16 | Feng-wen Yen | Iridium complexes and organic electroluminescence device using the same |
| JP5831654B1 (ja) | 2015-02-13 | 2015-12-09 | コニカミノルタ株式会社 | 芳香族複素環誘導体、それを用いた有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
| US10144867B2 (en) | 2015-02-13 | 2018-12-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10680183B2 (en) | 2015-02-15 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9929361B2 (en) | 2015-02-16 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP3061759B1 (en) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrile substituted dibenzofurans |
| US11056657B2 (en) | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
| US10600966B2 (en) | 2015-02-27 | 2020-03-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10686143B2 (en) | 2015-03-05 | 2020-06-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10270046B2 (en) | 2015-03-06 | 2019-04-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9780316B2 (en) | 2015-03-16 | 2017-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP3070144B1 (en) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
| US9911928B2 (en) | 2015-03-19 | 2018-03-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9871214B2 (en) | 2015-03-23 | 2018-01-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10529931B2 (en) | 2015-03-24 | 2020-01-07 | Universal Display Corporation | Organic Electroluminescent materials and devices |
| EP3072943B1 (en) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazole-substituted benzonitriles |
| US10297770B2 (en) | 2015-03-27 | 2019-05-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP3075737B1 (en) | 2015-03-31 | 2019-12-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes |
| US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20160293854A1 (en) | 2015-04-06 | 2016-10-06 | Universal Display Corporation | Organic Electroluminescent Materials and Devices |
| US11818949B2 (en) | 2015-04-06 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102424977B1 (ko) | 2015-04-14 | 2022-07-26 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
| US10403826B2 (en) | 2015-05-07 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10777749B2 (en) | 2015-05-07 | 2020-09-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9478758B1 (en) | 2015-05-08 | 2016-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9859510B2 (en) | 2015-05-15 | 2018-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10109799B2 (en) | 2015-05-21 | 2018-10-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10256411B2 (en) | 2015-05-21 | 2019-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10033004B2 (en) | 2015-06-01 | 2018-07-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9893305B2 (en) | 2015-06-01 | 2018-02-13 | Feng-wen Yen | Indenotriphenylene-based iridium complexes for organic electroluminescence device |
| US10818853B2 (en) | 2015-06-04 | 2020-10-27 | University Of Southern California | Organic electroluminescent materials and devices |
| US11925102B2 (en) | 2015-06-04 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10825997B2 (en) | 2015-06-25 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10873036B2 (en) | 2015-07-07 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9978956B2 (en) | 2015-07-15 | 2018-05-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11018309B2 (en) | 2015-08-03 | 2021-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11522140B2 (en) | 2015-08-17 | 2022-12-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10522769B2 (en) | 2015-08-18 | 2019-12-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10181564B2 (en) | 2015-08-26 | 2019-01-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10361381B2 (en) | 2015-09-03 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11706972B2 (en) | 2015-09-08 | 2023-07-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11302872B2 (en) | 2015-09-09 | 2022-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10770664B2 (en) | 2015-09-21 | 2020-09-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20170092880A1 (en) | 2015-09-25 | 2017-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10847728B2 (en) | 2015-10-01 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP3150606B1 (en) | 2015-10-01 | 2019-08-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes |
| US20180291028A1 (en) | 2015-10-01 | 2018-10-11 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
| EP3150604B1 (en) | 2015-10-01 | 2021-07-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
| US20180269407A1 (en) | 2015-10-01 | 2018-09-20 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes |
| US10593892B2 (en) | 2015-10-01 | 2020-03-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10991895B2 (en) | 2015-10-06 | 2021-04-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10177318B2 (en) | 2015-10-29 | 2019-01-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10388892B2 (en) | 2015-10-29 | 2019-08-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10388893B2 (en) | 2015-10-29 | 2019-08-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2017078182A1 (en) | 2015-11-04 | 2017-05-11 | Idemitsu Kosan Co., Ltd. | Benzimidazole fused heteroaryls |
| US10998507B2 (en) * | 2015-11-23 | 2021-05-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10476010B2 (en) | 2015-11-30 | 2019-11-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11174258B2 (en) | 2015-12-04 | 2021-11-16 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes |
| KR102630644B1 (ko) | 2015-12-17 | 2024-01-30 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
| US11024808B2 (en) | 2015-12-29 | 2021-06-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10957861B2 (en) | 2015-12-29 | 2021-03-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10135006B2 (en) | 2016-01-04 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10312459B2 (en) * | 2016-01-27 | 2019-06-04 | Nichem Fine Technology Co., Ltd. | Compound and organic electronic device using the same |
| US20170229663A1 (en) | 2016-02-09 | 2017-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10707427B2 (en) | 2016-02-09 | 2020-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10457864B2 (en) | 2016-02-09 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10600967B2 (en) | 2016-02-18 | 2020-03-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11094891B2 (en) | 2016-03-16 | 2021-08-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10276809B2 (en) | 2016-04-05 | 2019-04-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10236456B2 (en) | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10968229B2 (en) | 2016-04-12 | 2021-04-06 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
| US10566552B2 (en) | 2016-04-13 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11228003B2 (en) | 2016-04-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11228002B2 (en) | 2016-04-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11081647B2 (en) | 2016-04-22 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20170324049A1 (en) | 2016-05-05 | 2017-11-09 | Universal Display Corporation | Organic Electroluminescent Materials and Devices |
| US10985328B2 (en) | 2016-05-25 | 2021-04-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10468609B2 (en) | 2016-06-02 | 2019-11-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10686140B2 (en) | 2016-06-20 | 2020-06-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10862054B2 (en) * | 2016-06-20 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10727423B2 (en) | 2016-06-20 | 2020-07-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10651403B2 (en) | 2016-06-20 | 2020-05-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10957866B2 (en) | 2016-06-30 | 2021-03-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9929360B2 (en) | 2016-07-08 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10566547B2 (en) | 2016-07-11 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10153443B2 (en) | 2016-07-19 | 2018-12-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10720587B2 (en) | 2016-07-19 | 2020-07-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10205105B2 (en) | 2016-08-15 | 2019-02-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10608186B2 (en) | 2016-09-14 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10505127B2 (en) | 2016-09-19 | 2019-12-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP2018052929A (ja) * | 2016-09-21 | 2018-04-05 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、および照明装置 |
| US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11127906B2 (en) | 2016-10-03 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11183642B2 (en) | 2016-10-03 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11189804B2 (en) | 2016-10-03 | 2021-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11081658B2 (en) | 2016-10-03 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11239432B2 (en) | 2016-10-14 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10608185B2 (en) | 2016-10-17 | 2020-03-31 | Univeral Display Corporation | Organic electroluminescent materials and devices |
| US10236458B2 (en) | 2016-10-24 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12317745B2 (en) | 2016-11-09 | 2025-05-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10340464B2 (en) | 2016-11-10 | 2019-07-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10897016B2 (en) | 2016-11-14 | 2021-01-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10662196B2 (en) | 2016-11-17 | 2020-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10964893B2 (en) | 2016-11-17 | 2021-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10153445B2 (en) | 2016-11-21 | 2018-12-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10833276B2 (en) | 2016-11-21 | 2020-11-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11555048B2 (en) | 2016-12-01 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10490753B2 (en) | 2016-12-15 | 2019-11-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11545636B2 (en) | 2016-12-15 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11548905B2 (en) | 2016-12-15 | 2023-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10811618B2 (en) | 2016-12-19 | 2020-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11152579B2 (en) | 2016-12-28 | 2021-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20180190915A1 (en) | 2017-01-03 | 2018-07-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11201298B2 (en) | 2017-01-09 | 2021-12-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10804475B2 (en) | 2017-01-11 | 2020-10-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11545637B2 (en) | 2017-01-13 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10629820B2 (en) | 2017-01-18 | 2020-04-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10964904B2 (en) | 2017-01-20 | 2021-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11053268B2 (en) | 2017-01-20 | 2021-07-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11765968B2 (en) | 2017-01-23 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11050028B2 (en) | 2017-01-24 | 2021-06-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12089486B2 (en) | 2017-02-08 | 2024-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10686146B2 (en) * | 2017-02-13 | 2020-06-16 | Feng-wen Yen | Paracyclophane-based iridium complexes for organic electroluminescence device |
| US10978647B2 (en) | 2017-02-15 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10822361B2 (en) | 2017-02-22 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10745431B2 (en) | 2017-03-08 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10741780B2 (en) | 2017-03-10 | 2020-08-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10672998B2 (en) | 2017-03-23 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10873037B2 (en) | 2017-03-28 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10910577B2 (en) | 2017-03-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11158820B2 (en) | 2017-03-29 | 2021-10-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11056658B2 (en) | 2017-03-29 | 2021-07-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10862046B2 (en) | 2017-03-30 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11276829B2 (en) | 2017-03-31 | 2022-03-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11139443B2 (en) | 2017-03-31 | 2021-10-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10777754B2 (en) | 2017-04-11 | 2020-09-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11038117B2 (en) | 2017-04-11 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11101434B2 (en) | 2017-04-21 | 2021-08-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11084838B2 (en) | 2017-04-21 | 2021-08-10 | Universal Display Corporation | Organic electroluminescent materials and device |
| US10975113B2 (en) | 2017-04-21 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10910570B2 (en) | 2017-04-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11038137B2 (en) | 2017-04-28 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11117897B2 (en) | 2017-05-01 | 2021-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10941170B2 (en) | 2017-05-03 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11201299B2 (en) | 2017-05-04 | 2021-12-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10870668B2 (en) | 2017-05-05 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10862055B2 (en) | 2017-05-05 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10930864B2 (en) | 2017-05-10 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10822362B2 (en) | 2017-05-11 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10840459B2 (en) | 2017-05-18 | 2020-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11038115B2 (en) | 2017-05-18 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and device |
| US10790455B2 (en) | 2017-05-18 | 2020-09-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10934293B2 (en) | 2017-05-18 | 2021-03-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10944062B2 (en) | 2017-05-18 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10930862B2 (en) | 2017-06-01 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11174259B2 (en) | 2017-06-23 | 2021-11-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12098157B2 (en) | 2017-06-23 | 2024-09-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11802136B2 (en) | 2017-06-23 | 2023-10-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11608321B2 (en) | 2017-06-23 | 2023-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11814403B2 (en) | 2017-06-23 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11758804B2 (en) | 2017-06-23 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11678565B2 (en) | 2017-06-23 | 2023-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495757B2 (en) | 2017-06-23 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11552261B2 (en) | 2017-06-23 | 2023-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10968226B2 (en) | 2017-06-23 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11832510B2 (en) | 2017-06-23 | 2023-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11725022B2 (en) | 2017-06-23 | 2023-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11469382B2 (en) | 2017-07-12 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11917843B2 (en) | 2017-07-26 | 2024-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11765970B2 (en) | 2017-07-26 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11322691B2 (en) | 2017-07-26 | 2022-05-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11968883B2 (en) | 2017-07-26 | 2024-04-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11239433B2 (en) | 2017-07-26 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11744141B2 (en) | 2017-08-09 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11508913B2 (en) | 2017-08-10 | 2022-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11910699B2 (en) | 2017-08-10 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11349083B2 (en) | 2017-08-10 | 2022-05-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11723269B2 (en) | 2017-08-22 | 2023-08-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11462697B2 (en) | 2017-08-22 | 2022-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11437591B2 (en) | 2017-08-24 | 2022-09-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11605791B2 (en) | 2017-09-01 | 2023-03-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11696492B2 (en) | 2017-09-07 | 2023-07-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11424420B2 (en) | 2017-09-07 | 2022-08-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11444249B2 (en) | 2017-09-07 | 2022-09-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10608188B2 (en) | 2017-09-11 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11778897B2 (en) | 2017-09-20 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12389791B2 (en) | 2017-09-21 | 2025-08-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11325934B2 (en) * | 2017-09-29 | 2022-05-10 | Beijing Summer Sprout Technology Co., Ltd. | Organic luminescent materials containing tetraphenylene ligands |
| US12459946B2 (en) | 2017-10-05 | 2025-11-04 | Universal Display Corporation | Organic host materials for electroluminescent devices |
| US11214587B2 (en) | 2017-11-07 | 2022-01-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11910702B2 (en) | 2017-11-07 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent devices |
| US11183646B2 (en) | 2017-11-07 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11168103B2 (en) | 2017-11-17 | 2021-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12180230B2 (en) | 2017-11-28 | 2024-12-31 | University Of Southern California | Carbene compounds and organic electroluminescent devices |
| US11825735B2 (en) | 2017-11-28 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP3492480B1 (en) | 2017-11-29 | 2021-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP7147783B2 (ja) * | 2017-11-29 | 2022-10-05 | 三菱ケミカル株式会社 | イリジウム錯体化合物、該化合物および溶剤を含有する組成物、該化合物を含有する有機電界発光素子、表示装置および照明装置 |
| US11937503B2 (en) | 2017-11-30 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12075690B2 (en) | 2017-12-14 | 2024-08-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233205B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10971687B2 (en) | 2017-12-14 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233204B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11081659B2 (en) | 2018-01-10 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11700765B2 (en) | 2018-01-10 | 2023-07-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11515493B2 (en) | 2018-01-11 | 2022-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11271177B2 (en) | 2018-01-11 | 2022-03-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11367840B2 (en) | 2018-01-26 | 2022-06-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11845764B2 (en) | 2018-01-26 | 2023-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12029055B2 (en) | 2018-01-30 | 2024-07-02 | The University Of Southern California | OLED with hybrid emissive layer |
| US11957050B2 (en) | 2018-02-09 | 2024-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11239434B2 (en) | 2018-02-09 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11180519B2 (en) | 2018-02-09 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11342509B2 (en) | 2018-02-09 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11217757B2 (en) | 2018-03-12 | 2022-01-04 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11165028B2 (en) | 2018-03-12 | 2021-11-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11279722B2 (en) | 2018-03-12 | 2022-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11142538B2 (en) | 2018-03-12 | 2021-10-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11557733B2 (en) | 2018-03-12 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JPWO2019181465A1 (ja) | 2018-03-19 | 2021-04-30 | 日鉄ケミカル＆マテリアル株式会社 | 有機電界発光素子 |
| US12522608B2 (en) | 2018-04-13 | 2026-01-13 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11882759B2 (en) | 2018-04-13 | 2024-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11390639B2 (en) | 2018-04-13 | 2022-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11616203B2 (en) | 2018-04-17 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11753427B2 (en) | 2018-05-04 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11515494B2 (en) | 2018-05-04 | 2022-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11342513B2 (en) | 2018-05-04 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11793073B2 (en) | 2018-05-06 | 2023-10-17 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11459349B2 (en) | 2018-05-25 | 2022-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11450822B2 (en) | 2018-05-25 | 2022-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11716900B2 (en) | 2018-05-30 | 2023-08-01 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11404653B2 (en) | 2018-06-04 | 2022-08-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11925103B2 (en) | 2018-06-05 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11339182B2 (en) | 2018-06-07 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11228004B2 (en) | 2018-06-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11261207B2 (en) | 2018-06-25 | 2022-03-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11753425B2 (en) | 2018-07-11 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12378197B2 (en) | 2018-07-13 | 2025-08-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR20210038559A (ko) * | 2018-07-31 | 2021-04-07 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
| US12453279B2 (en) | 2018-08-22 | 2025-10-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233203B2 (en) | 2018-09-06 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12171137B2 (en) | 2018-09-10 | 2024-12-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11485706B2 (en) | 2018-09-11 | 2022-11-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11718634B2 (en) | 2018-09-14 | 2023-08-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11903305B2 (en) | 2018-09-24 | 2024-02-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11469383B2 (en) | 2018-10-08 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495752B2 (en) | 2018-10-08 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11476430B2 (en) | 2018-10-15 | 2022-10-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11515482B2 (en) | 2018-10-23 | 2022-11-29 | Universal Display Corporation | Deep HOMO (highest occupied molecular orbital) emitter device structures |
| US11469384B2 (en) | 2018-11-02 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11825736B2 (en) | 2018-11-19 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11963441B2 (en) | 2018-11-26 | 2024-04-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11515489B2 (en) | 2018-11-28 | 2022-11-29 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11889708B2 (en) | 2019-11-14 | 2024-01-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11716899B2 (en) | 2018-11-28 | 2023-08-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11690285B2 (en) | 2018-11-28 | 2023-06-27 | Universal Display Corporation | Electroluminescent devices |
| US11672165B2 (en) | 2018-11-28 | 2023-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11672176B2 (en) | 2018-11-28 | 2023-06-06 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11623936B2 (en) | 2018-12-11 | 2023-04-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
| US12281129B2 (en) | 2018-12-12 | 2025-04-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12167673B2 (en) | 2018-12-19 | 2024-12-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11812624B2 (en) | 2019-01-30 | 2023-11-07 | The University Of Southern California | Organic electroluminescent materials and devices |
| US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
| US12477890B2 (en) | 2019-02-01 | 2025-11-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11370809B2 (en) | 2019-02-08 | 2022-06-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11325932B2 (en) | 2019-02-08 | 2022-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12137605B2 (en) | 2019-02-08 | 2024-11-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11773320B2 (en) | 2019-02-21 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12250872B2 (en) | 2019-02-22 | 2025-03-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11557738B2 (en) | 2019-02-22 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11871653B2 (en) | 2019-02-22 | 2024-01-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11512093B2 (en) | 2019-03-04 | 2022-11-29 | Universal Display Corporation | Compound used for organic light emitting device (OLED), consumer product and formulation |
| US11739081B2 (en) | 2019-03-11 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11637261B2 (en) | 2019-03-12 | 2023-04-25 | Universal Display Corporation | Nanopatch antenna outcoupling structure for use in OLEDs |
| US11569480B2 (en) | 2019-03-12 | 2023-01-31 | Universal Display Corporation | Plasmonic OLEDs and vertical dipole emitters |
| US11963438B2 (en) | 2019-03-26 | 2024-04-16 | The University Of Southern California | Organic electroluminescent materials and devices |
| JP2020158491A (ja) | 2019-03-26 | 2020-10-01 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
| US12122793B2 (en) | 2019-03-27 | 2024-10-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12240865B2 (en) | 2019-03-27 | 2025-03-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11639363B2 (en) | 2019-04-22 | 2023-05-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12075691B2 (en) | 2019-04-30 | 2024-08-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11613550B2 (en) | 2019-04-30 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices comprising benzimidazole-containing metal complexes |
| US11560398B2 (en) | 2019-05-07 | 2023-01-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495756B2 (en) | 2019-05-07 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12103942B2 (en) | 2019-05-13 | 2024-10-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11827651B2 (en) | 2019-05-13 | 2023-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11634445B2 (en) | 2019-05-21 | 2023-04-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12010859B2 (en) | 2019-05-24 | 2024-06-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11647667B2 (en) | 2019-06-14 | 2023-05-09 | Universal Display Corporation | Organic electroluminescent compounds and organic light emitting devices using the same |
| US12077550B2 (en) | 2019-07-02 | 2024-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11920070B2 (en) | 2019-07-12 | 2024-03-05 | The University Of Southern California | Luminescent janus-type, two-coordinated metal complexes |
| US11685754B2 (en) | 2019-07-22 | 2023-06-27 | Universal Display Corporation | Heteroleptic organic electroluminescent materials |
| US11926638B2 (en) | 2019-07-22 | 2024-03-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12281128B2 (en) | 2019-07-30 | 2025-04-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11708355B2 (en) | 2019-08-01 | 2023-07-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12295251B2 (en) | 2019-08-01 | 2025-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20210040129A1 (en) * | 2019-08-08 | 2021-02-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN112341498B (zh) * | 2019-08-08 | 2024-09-10 | 环球展览公司 | 有机电致发光材料和装置 |
| US11985888B2 (en) | 2019-08-12 | 2024-05-14 | The Regents Of The University Of Michigan | Organic electroluminescent device |
| US12227525B2 (en) | 2019-08-14 | 2025-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11374181B2 (en) | 2019-08-14 | 2022-06-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11930699B2 (en) | 2019-08-15 | 2024-03-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12139501B2 (en) | 2019-08-16 | 2024-11-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12234249B2 (en) | 2019-08-21 | 2025-02-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11925105B2 (en) | 2019-08-26 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11937494B2 (en) | 2019-08-28 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11600787B2 (en) | 2019-08-30 | 2023-03-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11820783B2 (en) | 2019-09-06 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN112457349B (zh) | 2019-09-06 | 2024-10-15 | 环球展览公司 | 有机电致发光材料和装置 |
| US12144244B2 (en) | 2019-09-10 | 2024-11-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12331065B2 (en) | 2019-09-26 | 2025-06-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11999886B2 (en) | 2019-09-26 | 2024-06-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12486296B2 (en) | 2019-10-02 | 2025-12-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11864458B2 (en) | 2019-10-08 | 2024-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11950493B2 (en) | 2019-10-15 | 2024-04-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11697653B2 (en) | 2019-10-21 | 2023-07-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12522565B2 (en) | 2019-10-25 | 2026-01-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN120463731A (zh) | 2019-10-25 | 2025-08-12 | 环球展览公司 | 有机电致发光材料和装置 |
| US11919914B2 (en) | 2019-10-25 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11765965B2 (en) | 2019-10-30 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20210135130A1 (en) | 2019-11-04 | 2021-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12538698B2 (en) | 2020-01-06 | 2026-01-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12201013B2 (en) | 2020-01-08 | 2025-01-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12187751B2 (en) | 2020-01-08 | 2025-01-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11778895B2 (en) | 2020-01-13 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12426495B2 (en) | 2020-01-28 | 2025-09-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11917900B2 (en) | 2020-01-28 | 2024-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11932660B2 (en) | 2020-01-29 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12245502B2 (en) | 2020-02-03 | 2025-03-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12156463B2 (en) | 2020-02-07 | 2024-11-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12084465B2 (en) | 2020-02-24 | 2024-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12324348B2 (en) | 2020-02-28 | 2025-06-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12234251B2 (en) | 2020-03-04 | 2025-02-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12018035B2 (en) | 2020-03-23 | 2024-06-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12129269B2 (en) | 2020-04-13 | 2024-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12279520B2 (en) | 2020-04-22 | 2025-04-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11970508B2 (en) | 2020-04-22 | 2024-04-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12466844B2 (en) | 2020-05-13 | 2025-11-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12286410B2 (en) | 2020-05-18 | 2025-04-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12035613B2 (en) | 2020-05-26 | 2024-07-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12275747B2 (en) | 2020-06-02 | 2025-04-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12247043B2 (en) | 2020-06-11 | 2025-03-11 | Universal Display Corporation | Organic electroluminescent material and formulations, and its various uses as hosts, fluorescent dopants, and acceptors in organic light emitting diodes |
| US12279516B2 (en) | 2020-06-17 | 2025-04-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12419188B2 (en) | 2020-06-30 | 2025-09-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12336427B2 (en) | 2020-07-09 | 2025-06-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP3937268B1 (en) | 2020-07-10 | 2025-05-07 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
| US12157748B2 (en) | 2020-07-30 | 2024-12-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12369487B2 (en) | 2020-08-05 | 2025-07-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12065451B2 (en) | 2020-08-19 | 2024-08-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12289986B2 (en) | 2020-08-25 | 2025-04-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12369488B2 (en) | 2020-09-09 | 2025-07-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12486295B2 (en) | 2020-09-14 | 2025-12-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP2023541976A (ja) | 2020-09-18 | 2023-10-04 | 三星ディスプレイ株式會社 | 有機エレクトロルミネッセンス素子 |
| US12221455B2 (en) | 2020-09-24 | 2025-02-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12252499B2 (en) | 2020-09-29 | 2025-03-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12460128B2 (en) | 2020-10-02 | 2025-11-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12497420B2 (en) | 2020-10-02 | 2025-12-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12486451B2 (en) | 2020-10-02 | 2025-12-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12435102B2 (en) | 2020-10-02 | 2025-10-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12286447B2 (en) | 2020-10-06 | 2025-04-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12520713B2 (en) | 2020-10-08 | 2026-01-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12486288B2 (en) | 2020-10-12 | 2025-12-02 | University Of Southern California | Fast phosphors utilizing HP2H ligands |
| US12312365B2 (en) | 2020-10-12 | 2025-05-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12137606B2 (en) | 2020-10-20 | 2024-11-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12247042B2 (en) | 2020-10-26 | 2025-03-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12245504B2 (en) | 2020-10-26 | 2025-03-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR20220056727A (ko) * | 2020-10-28 | 2022-05-06 | 삼성전자주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 진단용 조성물 |
| US12187748B2 (en) | 2020-11-02 | 2025-01-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12262631B2 (en) | 2020-11-10 | 2025-03-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220158096A1 (en) | 2020-11-16 | 2022-05-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12528833B2 (en) | 2020-11-18 | 2026-01-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12516078B2 (en) | 2020-11-24 | 2026-01-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12325717B2 (en) | 2020-11-24 | 2025-06-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220165967A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12534485B2 (en) | 2020-11-24 | 2026-01-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12331064B2 (en) | 2020-12-09 | 2025-06-17 | University Of Southern California | Tandem carbene phosphors |
| US12342716B2 (en) | 2020-12-09 | 2025-06-24 | University Of Southern California | Tandem-carbene phosphors |
| US12466848B2 (en) | 2020-12-10 | 2025-11-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12398164B2 (en) | 2021-02-01 | 2025-08-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12459966B2 (en) | 2021-02-02 | 2025-11-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220271241A1 (en) | 2021-02-03 | 2022-08-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12497419B2 (en) | 2021-02-22 | 2025-12-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12484437B2 (en) | 2021-02-26 | 2025-11-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4060758A3 (en) | 2021-02-26 | 2023-03-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4059915B1 (en) | 2021-02-26 | 2025-12-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220298192A1 (en) | 2021-03-05 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12428599B2 (en) | 2021-03-09 | 2025-09-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220298190A1 (en) | 2021-03-12 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12421262B2 (en) | 2021-03-15 | 2025-09-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220324892A1 (en) * | 2021-03-23 | 2022-10-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220340607A1 (en) | 2021-04-05 | 2022-10-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12480042B2 (en) | 2021-04-09 | 2025-11-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4075531A1 (en) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
| US20220352478A1 (en) | 2021-04-14 | 2022-11-03 | Universal Display Corporation | Organic eletroluminescent materials and devices |
| US20220407020A1 (en) | 2021-04-23 | 2022-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230006149A1 (en) | 2021-04-23 | 2023-01-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12473317B2 (en) | 2021-06-04 | 2025-11-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230133787A1 (en) | 2021-06-08 | 2023-05-04 | University Of Southern California | Molecular Alignment of Homoleptic Iridium Phosphors |
| US12495715B2 (en) | 2021-06-29 | 2025-12-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12520715B2 (en) | 2021-07-16 | 2026-01-06 | University Of Southern California | Organic electroluminescent materials and devices |
| US12507586B2 (en) | 2021-07-21 | 2025-12-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12514110B2 (en) | 2021-08-06 | 2025-12-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12473318B2 (en) | 2021-10-08 | 2025-11-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230117045A1 (en) * | 2021-10-12 | 2023-04-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12509628B2 (en) | 2021-12-16 | 2025-12-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12414433B2 (en) | 2022-02-11 | 2025-09-09 | Universal Display Corporation | Organic electroluminescent devices |
| EP4231804A3 (en) | 2022-02-16 | 2023-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230292592A1 (en) | 2022-03-09 | 2023-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230337516A1 (en) | 2022-04-18 | 2023-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230389421A1 (en) | 2022-05-24 | 2023-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240016051A1 (en) | 2022-06-28 | 2024-01-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240107880A1 (en) | 2022-08-17 | 2024-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240188316A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240188319A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240180025A1 (en) | 2022-10-27 | 2024-05-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240196730A1 (en) | 2022-10-27 | 2024-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240188419A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240247017A1 (en) | 2022-12-14 | 2024-07-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20250204239A1 (en) | 2023-12-15 | 2025-06-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20250204238A1 (en) | 2023-12-15 | 2025-06-19 | Universal Display Corporation | Organic electroluminscent materials and devices |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1478372A (zh) * | 2000-11-30 | 2004-02-25 | ������������ʽ���� | 发光器件和显示装置 |
| CN1678617A (zh) * | 2002-08-24 | 2005-10-05 | 科文有机半导体有限公司 | 铑和铱配合物 |
Family Cites Families (167)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4769292A (en) * | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
| GB8909011D0 (en) * | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
| DE69412567T2 (de) | 1993-11-01 | 1999-02-04 | Hodogaya Chemical Co., Ltd., Tokio/Tokyo | Aminverbindung und sie enthaltende Elektrolumineszenzvorrichtung |
| US5503910A (en) * | 1994-03-29 | 1996-04-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
| US6309514B1 (en) * | 1994-11-07 | 2001-10-30 | Ti Properties, Inc. | Process for breaking chemical bonds |
| US5703436A (en) * | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
| US5707745A (en) * | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
| US5554220A (en) * | 1995-05-19 | 1996-09-10 | The Trustees Of Princeton University | Method and apparatus using organic vapor phase deposition for the growth of organic thin films with large optical non-linearities |
| US5929194A (en) * | 1996-02-23 | 1999-07-27 | The Dow Chemical Company | Crosslinkable or chain extendable polyarylpolyamines and films thereof |
| US6939625B2 (en) | 1996-06-25 | 2005-09-06 | Nôrthwestern University | Organic light-emitting diodes and methods for assembly and enhanced charge injection |
| US5844363A (en) * | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
| US5986401A (en) * | 1997-03-20 | 1999-11-16 | The Trustee Of Princeton University | High contrast transparent organic light emitting device display |
| US5834893A (en) * | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
| US6013982A (en) * | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
| US6091195A (en) * | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
| US6303238B1 (en) * | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
| JP4963754B2 (ja) | 1997-10-23 | 2012-06-27 | イシス イノベイション リミテッド | 光放射デンドリマー及び光放射装置 |
| US6337102B1 (en) * | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
| US6087196A (en) * | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
| US6528187B1 (en) | 1998-09-08 | 2003-03-04 | Fuji Photo Film Co., Ltd. | Material for luminescence element and luminescence element using the same |
| US6097147A (en) * | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
| US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
| US6166489A (en) * | 1998-09-15 | 2000-12-26 | The Trustees Of Princeton University | Light emitting device using dual light emitting stacks to achieve full-color emission |
| EP1181842B1 (en) | 1999-03-23 | 2016-05-25 | University Of Southern California | Cyclometallated metal complexes as phosphorescent dopants in organic leds |
| US7001536B2 (en) * | 1999-03-23 | 2006-02-21 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
| EP1729327B2 (en) | 1999-05-13 | 2022-08-10 | The Trustees Of Princeton University | Use of a phosphorescent iridium compound as emissive molecule in an organic light emitting device |
| US6294398B1 (en) * | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
| US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
| EP2278637B2 (en) | 1999-12-01 | 2021-06-09 | The Trustees of Princeton University | Complexes of form L2MX |
| US6821645B2 (en) * | 1999-12-27 | 2004-11-23 | Fuji Photo Film Co., Ltd. | Light-emitting material comprising orthometalated iridium complex, light-emitting device, high efficiency red light-emitting device, and novel iridium complex |
| KR100377321B1 (ko) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
| GB0002936D0 (en) | 2000-02-09 | 2000-03-29 | Isis Innovation | Improved dendrimers |
| US20020121638A1 (en) | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
| JP5241053B2 (ja) | 2000-08-11 | 2013-07-17 | ザ、トラスティーズ オブ プリンストン ユニバーシティ | 有機金属化合物及び放射移行有機電気燐光体 |
| US6911271B1 (en) * | 2000-08-11 | 2005-06-28 | The University Of Southern California | Organometallic platinum complexes for phosphorescence based organic light emitting devices |
| US6939624B2 (en) * | 2000-08-11 | 2005-09-06 | Universal Display Corporation | Organometallic compounds and emission-shifting organic electrophosphorescence |
| WO2002044189A1 (fr) * | 2000-11-30 | 2002-06-06 | Canon Kabushiki Kaisha | Element luminescent et afficheur |
| US6579630B2 (en) | 2000-12-07 | 2003-06-17 | Canon Kabushiki Kaisha | Deuterated semiconducting organic compounds used for opto-electronic devices |
| JP3812730B2 (ja) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
| DE10104426A1 (de) * | 2001-02-01 | 2002-08-08 | Covion Organic Semiconductors | Verfahren zur Herstellung von hochreinen, tris-ortho-metallierten Organo-Iridium-Verbindungen |
| CN1277872C (zh) | 2001-02-20 | 2006-10-04 | 安德鲁斯街大学管理处 | 含金属的树状物 |
| JP4438042B2 (ja) | 2001-03-08 | 2010-03-24 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
| JP4307000B2 (ja) | 2001-03-08 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
| DE10116962A1 (de) * | 2001-04-05 | 2002-10-10 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
| JP4310077B2 (ja) | 2001-06-19 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物及び有機発光素子 |
| WO2003001616A2 (en) | 2001-06-20 | 2003-01-03 | Showa Denko K.K. | Light emitting material and organic light-emitting device |
| WO2003006468A2 (en) * | 2001-07-09 | 2003-01-23 | Merck Patent Gmbh | Polymerisable charge transport compounds |
| US7071615B2 (en) * | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
| KR100917347B1 (ko) * | 2001-08-29 | 2009-09-16 | 더 트러스티즈 오브 프린스턴 유니버시티 | 금속 착물들을 포함하는 캐리어 블로킹층들을 갖는 유기발광 디바이스들 |
| US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
| US7431968B1 (en) * | 2001-09-04 | 2008-10-07 | The Trustees Of Princeton University | Process and apparatus for organic vapor jet deposition |
| JP2003073387A (ja) | 2001-09-04 | 2003-03-12 | Canon Inc | 金属配位化合物及び有機発光素子 |
| US6835469B2 (en) * | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
| US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
| US6863997B2 (en) | 2001-12-28 | 2005-03-08 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
| KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
| DE60305570T2 (de) * | 2002-04-24 | 2007-05-03 | Merck Patent Gmbh | Reaktive mesogene Benzodithiophene |
| US20030230980A1 (en) * | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
| US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
| EP2264122A3 (en) | 2002-08-27 | 2011-05-11 | Fujifilm Corporation | Organometallic complexes, organic electroluminescent devices and organic electroluminescent displays |
| GB0219987D0 (en) * | 2002-08-28 | 2002-10-09 | Isis Innovation | Intramolecular interactions in organometallics |
| US20040086743A1 (en) * | 2002-11-06 | 2004-05-06 | Brown Cory S. | Organometallic compounds for use in electroluminescent devices |
| CA2505384C (en) | 2002-11-08 | 2012-01-17 | National Research Council Of Canada | Thermally crosslinkable materials and multi-layered devices therefrom |
| US6687266B1 (en) | 2002-11-08 | 2004-02-03 | Universal Display Corporation | Organic light emitting materials and devices |
| JP4365199B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
| JP4365196B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
| US7338722B2 (en) | 2003-03-24 | 2008-03-04 | The University Of Southern California | Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir |
| US7090928B2 (en) | 2003-04-01 | 2006-08-15 | The University Of Southern California | Binuclear compounds |
| KR101162933B1 (ko) | 2003-04-15 | 2012-07-05 | 메르크 파텐트 게엠베하 | 매트릭스 재료 및 방출 가능 유기 반도체의 혼합물, 그의 용도 및 상기 혼합물을 함유하는 전자 부품 |
| US7029765B2 (en) * | 2003-04-22 | 2006-04-18 | Universal Display Corporation | Organic light emitting devices having reduced pixel shrinkage |
| KR101032355B1 (ko) | 2003-05-29 | 2011-05-03 | 신닛테츠가가쿠 가부시키가이샤 | 유기 전계 발광 소자 |
| US7955716B2 (en) * | 2003-06-09 | 2011-06-07 | Hitachi Chemical Co., Ltd. | Metal coordination compound, polymer composition, and organic electroluminescent device employing same |
| JP2005011610A (ja) | 2003-06-18 | 2005-01-13 | Nippon Steel Chem Co Ltd | 有機電界発光素子 |
| US20050025993A1 (en) | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
| US7198859B2 (en) * | 2003-07-25 | 2007-04-03 | Universal Display Corporation | Materials and structures for enhancing the performance of organic light emitting devices |
| TWI287567B (en) * | 2003-07-30 | 2007-10-01 | Chi Mei Optoelectronics Corp | Light-emitting element and iridium complex |
| TWI390006B (zh) | 2003-08-07 | 2013-03-21 | Nippon Steel Chemical Co | Organic EL materials with aluminum clamps |
| DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
| DE602004017027D1 (de) | 2003-08-29 | 2008-11-20 | Showa Denko Kk | Phosphoreszierende polymerverbindung und darauf basierende organische lichtemittierende vorrichtung |
| GB0321781D0 (en) | 2003-09-17 | 2003-10-15 | Toppan Printing Company Ltd | Electroluminescent device |
| US20060269780A1 (en) | 2003-09-25 | 2006-11-30 | Takayuki Fukumatsu | Organic electroluminescent device |
| JP4822687B2 (ja) | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | 有機電界発光素子 |
| US7629061B2 (en) * | 2004-01-16 | 2009-12-08 | Osram Opto Semiconductors Gmbh | Heterostructure devices using cross-linkable polymers |
| US7332232B2 (en) | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
| EP2918590A1 (en) | 2004-03-11 | 2015-09-16 | Mitsubishi Chemical Corporation | Composition for charge-transport film and ionic compound, charge-transport film and organic electroluminescence device using the same, and production method of the organic electroluminescence device and production method of the charge-transport film |
| TW200531592A (en) | 2004-03-15 | 2005-09-16 | Nippon Steel Chemical Co | Organic electroluminescent device |
| JP4869565B2 (ja) | 2004-04-23 | 2012-02-08 | 富士フイルム株式会社 | 有機電界発光素子 |
| US7491823B2 (en) | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
| US7279704B2 (en) * | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
| US7534505B2 (en) | 2004-05-18 | 2009-05-19 | The University Of Southern California | Organometallic compounds for use in electroluminescent devices |
| US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
| US7154114B2 (en) | 2004-05-18 | 2006-12-26 | Universal Display Corporation | Cyclometallated iridium carbene complexes for use as hosts |
| US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
| TW200613514A (en) | 2004-05-21 | 2006-05-01 | Showa Denko Kk | Polymer light-emitting material and organic light emitting element |
| WO2005124889A1 (en) | 2004-06-09 | 2005-12-29 | E.I. Dupont De Nemours And Company | Organometallic compounds and devices made with such compounds |
| WO2005123873A1 (ja) | 2004-06-17 | 2005-12-29 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| CA2568667A1 (en) | 2004-06-28 | 2006-01-05 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with triazoles and benzotriazoles |
| US20060008670A1 (en) | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
| US7709100B2 (en) * | 2004-07-07 | 2010-05-04 | Universal Display Corporation | Electroluminescent efficiency |
| KR101214539B1 (ko) * | 2004-07-07 | 2012-12-24 | 유니버셜 디스플레이 코포레이션 | 안정하면서 효율이 높은 전기발광 재료 |
| US20060008671A1 (en) * | 2004-07-07 | 2006-01-12 | Raymond Kwong | Electroluminescent efficiency |
| US7504657B2 (en) | 2004-07-23 | 2009-03-17 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display and illuminator |
| JP2006124373A (ja) | 2004-09-29 | 2006-05-18 | Canon Inc | 化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
| DE102004057072A1 (de) | 2004-11-25 | 2006-06-01 | Basf Ag | Verwendung von Übergangsmetall-Carbenkomplexen in organischen Licht-emittierenden Dioden (OLEDs) |
| US20060134459A1 (en) * | 2004-12-17 | 2006-06-22 | Shouquan Huo | OLEDs with mixed-ligand cyclometallated complexes |
| US8362463B2 (en) | 2004-12-30 | 2013-01-29 | E. I. Du Pont De Nemours And Company | Organometallic complexes |
| JPWO2006082742A1 (ja) | 2005-02-04 | 2008-06-26 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| KR100803125B1 (ko) * | 2005-03-08 | 2008-02-14 | 엘지전자 주식회사 | 적색 인광 화합물 및 이를 사용한 유기전계발광소자 |
| KR100797469B1 (ko) * | 2005-03-08 | 2008-01-24 | 엘지전자 주식회사 | 적색 인광 화합물 및 이를 사용한 유기전계발광소자 |
| JP5125502B2 (ja) | 2005-03-16 | 2013-01-23 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子 |
| DE102005014284A1 (de) | 2005-03-24 | 2006-09-28 | Basf Ag | Verwendung von Verbindungen, welche aromatische oder heteroaromatische über Carbonyl-Gruppen enthaltende Gruppen verbundene Ringe enthalten, als Matrixmaterialien in organischen Leuchtdioden |
| JPWO2006103874A1 (ja) | 2005-03-29 | 2008-09-04 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| US8231983B2 (en) | 2005-04-18 | 2012-07-31 | Konica Minolta Holdings Inc. | Organic electroluminescent device, display and illuminating device |
| US7807275B2 (en) | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
| US8007927B2 (en) | 2007-12-28 | 2011-08-30 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
| US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
| JP4533796B2 (ja) | 2005-05-06 | 2010-09-01 | 富士フイルム株式会社 | 有機電界発光素子 |
| US7851072B2 (en) * | 2005-05-19 | 2010-12-14 | Universal Display Corporation | Stable and efficient electroluminescent materials |
| KR20140082808A (ko) | 2005-05-31 | 2014-07-02 | 유니버셜 디스플레이 코포레이션 | 인광 발광 다이오드에서의 트리페닐렌 호스트 |
| CN101193875B (zh) | 2005-06-07 | 2011-05-11 | 新日铁化学株式会社 | 有机金属络合物和使用了其的有机电致发光元件 |
| KR101294905B1 (ko) | 2005-06-27 | 2013-08-09 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전기 전도성 중합체 조성물 |
| EP2036915A1 (en) | 2005-06-30 | 2009-03-18 | Koninklijke Philips Electronics N.V. | Electro luminescent metal complexes |
| JP5076891B2 (ja) | 2005-07-01 | 2012-11-21 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| WO2007028417A1 (en) | 2005-09-07 | 2007-03-15 | Technische Universität Braunschweig | Triplett emitter having condensed five-membered rings |
| JP4887731B2 (ja) | 2005-10-26 | 2012-02-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| WO2007063796A1 (ja) | 2005-12-01 | 2007-06-07 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子 |
| EP1956022B1 (en) | 2005-12-01 | 2012-07-25 | Nippon Steel Chemical Co., Ltd. | Compound for organic electroluminescent element and organic electroluminescent element |
| DE102005057963A1 (de) | 2005-12-05 | 2007-06-06 | Merck Patent Gmbh | Verfahren zur Herstellung ortho-metallierter Metallverbindungen |
| ATE553111T1 (de) | 2006-02-10 | 2012-04-15 | Universal Display Corp | Metallkomplexe aus imidazoä1,2-füphenanthridin- liganden und deren verwendung in oled vorrichtungen |
| JP4823730B2 (ja) | 2006-03-20 | 2011-11-24 | 新日鐵化学株式会社 | 発光層化合物及び有機電界発光素子 |
| JP4785594B2 (ja) * | 2006-03-31 | 2011-10-05 | キヤノン株式会社 | イリジウム錯体の製造方法、有機エレクトロルミネッセンス素子および表示装置 |
| KR101551591B1 (ko) | 2006-04-26 | 2015-09-08 | 이데미쓰 고산 가부시키가이샤 | 방향족 아민 유도체 및 그들을 이용한 유기 전기 발광 소자 |
| EP2018090A4 (en) | 2006-05-11 | 2010-12-01 | Idemitsu Kosan Co | ORGANIC ELECTROLUMINESCENCE DEVICE |
| KR20090016684A (ko) | 2006-06-02 | 2009-02-17 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자용 재료 및 그것을 이용한 유기 전기발광 소자 |
| WO2008023549A1 (en) | 2006-08-23 | 2008-02-28 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivatives and organic electroluminescent devices made by using the same |
| JP5589251B2 (ja) | 2006-09-21 | 2014-09-17 | 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材料 |
| EP2080762B1 (en) | 2006-11-09 | 2016-09-14 | Nippon Steel & Sumikin Chemical Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device |
| KR100779009B1 (ko) * | 2006-11-20 | 2007-11-28 | 광주과학기술원 | 이리듐 착체, 카바졸 유도체 및 이들을 가지는 공중합체 |
| CN101535256B (zh) | 2006-11-24 | 2013-05-22 | 出光兴产株式会社 | 芳香族胺衍生物及使用其的有机电致发光元件 |
| US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
| TWI481089B (zh) * | 2006-12-28 | 2015-04-11 | Universal Display Corp | 長使用期限之磷光性有機發光裝置結構 |
| KR101532798B1 (ko) | 2007-02-23 | 2015-06-30 | 바스프 에스이 | 벤조트리아졸과의 전계발광 금속 착물 |
| JP5677836B2 (ja) | 2007-04-26 | 2015-02-25 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | フェノチアジン−ｓ−オキシドまたはフェノチアジン−ｓ，ｓ−ジオキシド基を含有するシラン、およびｏｌｅｄにおけるその使用 |
| WO2008156879A1 (en) | 2007-06-20 | 2008-12-24 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
| US8440826B2 (en) | 2007-06-22 | 2013-05-14 | Basf Se | Light emitting Cu (I) complexes |
| EP2165377B1 (de) | 2007-07-05 | 2021-04-28 | UDC Ireland Limited | Organische leuchtdioden enthaltend carben-übergangsmetall-komplex-emitter und mindestens eine verbindung ausgewählt aus disilylcarbazolen; disilyldibenzofuranen, disilyldibenzothiophenen, disilyldibenzophospholen, disilyldibenzothiophen-s-oxiden und disilyldibenzothiophen-s,s-dioxiden |
| US8221907B2 (en) | 2007-07-07 | 2012-07-17 | Idemitsu Kosan Co., Ltd. | Chrysene derivative and organic electroluminescent device using the same |
| JPWO2009008198A1 (ja) | 2007-07-07 | 2010-09-02 | 出光興産株式会社 | ナフタレン誘導体、有機ｅｌ素子用材料及びそれを用いた有機ｅｌ素子 |
| US8779655B2 (en) | 2007-07-07 | 2014-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
| WO2009008205A1 (ja) | 2007-07-07 | 2009-01-15 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス素子用材料 |
| US20090045731A1 (en) | 2007-07-07 | 2009-02-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
| JPWO2009008099A1 (ja) | 2007-07-10 | 2010-09-02 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
| US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
| CN101688052A (zh) | 2007-07-27 | 2010-03-31 | E.I.内穆尔杜邦公司 | 包含无机纳米颗粒的导电聚合物的含水分散体 |
| KR101565724B1 (ko) | 2007-08-08 | 2015-11-03 | 유니버셜 디스플레이 코포레이션 | 트리페닐렌기를 포함하는 벤조 융합 티오펜 또는 벤조 융합 푸란 화합물 |
| JP2009040728A (ja) | 2007-08-09 | 2009-02-26 | Canon Inc | 有機金属錯体及びこれを用いた有機発光素子 |
| EP2203461B1 (de) | 2007-10-17 | 2011-08-10 | Basf Se | Übergangsmetallkomplexe mit verbrückten carbenliganden und deren verwendung in oleds |
| US20090101870A1 (en) | 2007-10-22 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Electron transport bi-layers and devices made with such bi-layers |
| US7914908B2 (en) | 2007-11-02 | 2011-03-29 | Global Oled Technology Llc | Organic electroluminescent device having an azatriphenylene derivative |
| DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
| KR101353635B1 (ko) | 2007-11-15 | 2014-01-20 | 이데미쓰 고산 가부시키가이샤 | 벤조크리센 유도체 및 이것을 사용한 유기 전계 발광 소자 |
| CN101874316B (zh) | 2007-11-22 | 2012-09-05 | 出光兴产株式会社 | 有机el元件以及含有机el材料的溶液 |
| WO2009066779A1 (ja) | 2007-11-22 | 2009-05-28 | Idemitsu Kosan Co., Ltd. | 有機ｅｌ素子 |
| WO2009073245A1 (en) | 2007-12-06 | 2009-06-11 | Universal Display Corporation | Light-emitting organometallic complexes |
| US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
| CN105859792A (zh) | 2008-02-12 | 2016-08-17 | 巴斯夫欧洲公司 | 具有二苯并[f,h]喹噁啉的电致发光金属络合物 |
-
2008
- 2008-03-07 WO PCT/US2008/056324 patent/WO2009073245A1/en not_active Ceased
- 2008-03-07 US US12/044,801 patent/US8778508B2/en active Active
- 2008-05-05 TW TW105143131A patent/TW201713747A/zh unknown
- 2008-05-05 TW TW104112273A patent/TWI577781B/zh active
- 2008-05-05 TW TW097116553A patent/TWI493015B/zh active
-
2014
- 2014-06-04 US US14/295,696 patent/US9899612B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1478372A (zh) * | 2000-11-30 | 2004-02-25 | ������������ʽ���� | 发光器件和显示装置 |
| CN1678617A (zh) * | 2002-08-24 | 2005-10-05 | 科文有机半导体有限公司 | 铑和铱配合物 |
Also Published As
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| TWI577781B (zh) | 2017-04-11 |
| TW201527486A (zh) | 2015-07-16 |
| US20140284585A1 (en) | 2014-09-25 |
| TW201713747A (en) | 2017-04-16 |
| US20090108737A1 (en) | 2009-04-30 |
| TW200925240A (en) | 2009-06-16 |
| US9899612B2 (en) | 2018-02-20 |
| WO2009073245A1 (en) | 2009-06-11 |
| US8778508B2 (en) | 2014-07-15 |
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