TWI626296B - 包含氮雜苯并咪唑碳烯配位體的金屬錯合物及其於ｏｌｅｄ中的用途 - Google Patents
包含氮雜苯并咪唑碳烯配位體的金屬錯合物及其於ｏｌｅｄ中的用途 Download PDFInfo
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- TWI626296B TWI626296B TW106103305A TW106103305A TWI626296B TW I626296 B TWI626296 B TW I626296B TW 106103305 A TW106103305 A TW 106103305A TW 106103305 A TW106103305 A TW 106103305A TW I626296 B TWI626296 B TW I626296B
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- 239000003446 ligand Substances 0.000 title claims abstract description 166
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 229910052751 metal Inorganic materials 0.000 title abstract description 15
- 239000002184 metal Substances 0.000 title abstract description 15
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 178
- 239000000463 material Substances 0.000 claims abstract description 86
- 239000011159 matrix material Substances 0.000 claims abstract description 36
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- 230000000007 visual effect Effects 0.000 claims abstract description 15
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 334
- 125000005842 heteroatom Chemical group 0.000 claims description 303
- 125000003118 aryl group Chemical group 0.000 claims description 204
- 125000000217 alkyl group Chemical class 0.000 claims description 160
- 125000001072 heteroaryl group Chemical group 0.000 claims description 142
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 133
- 125000000524 functional group Chemical group 0.000 claims description 110
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 102
- 239000000370 acceptor Substances 0.000 claims description 78
- -1 heteroaryl Radical Chemical class 0.000 claims description 72
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 67
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- 125000001424 substituent group Chemical group 0.000 claims description 48
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
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- 125000004122 cyclic group Chemical group 0.000 claims description 22
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- 125000006413 ring segment Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 17
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- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 claims description 6
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000013086 organic photovoltaic Methods 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910021115 PF 6 Inorganic materials 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 241000162682 Heterogen Species 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 75
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 21
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
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- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 description 18
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- 150000001721 carbon Chemical group 0.000 description 15
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- 238000001228 spectrum Methods 0.000 description 10
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 9
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- 229920001577 copolymer Polymers 0.000 description 9
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- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 8
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- GQENPXQJRUSMDY-UHFFFAOYSA-N [Ir+].ClC1=CCCC=CCC1 Chemical class [Ir+].ClC1=CCCC=CCC1 GQENPXQJRUSMDY-UHFFFAOYSA-N 0.000 description 7
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- 238000001914 filtration Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- 229910052723 transition metal Inorganic materials 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
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- KJFSSYNBXWZUQE-UHFFFAOYSA-M 3-phenyl-1-propan-2-ylimidazo[4,5-b]pyridin-1-ium;iodide Chemical compound [I-].C12=NC=CC=C2[N+](C(C)C)=CN1C1=CC=CC=C1 KJFSSYNBXWZUQE-UHFFFAOYSA-M 0.000 description 4
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- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 4
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
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- OZRQQVJZHUAPTI-UHFFFAOYSA-M 1,3-diphenylimidazo[4,5-b]pyridin-3-ium;chloride Chemical compound [Cl-].C12=NC=CC=C2[N+](C=2C=CC=CC=2)=CN1C1=CC=CC=C1 OZRQQVJZHUAPTI-UHFFFAOYSA-M 0.000 description 3
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- NZWKAYMFHNNNPX-UHFFFAOYSA-N 2-n,3-n-diphenylpyridine-2,3-diamine Chemical compound C=1C=CN=C(NC=2C=CC=CC=2)C=1NC1=CC=CC=C1 NZWKAYMFHNNNPX-UHFFFAOYSA-N 0.000 description 3
- KCHQXPGUJBVNTN-UHFFFAOYSA-N 4,4-diphenylbut-3-en-2-one Chemical compound C=1C=CC=CC=1C(=CC(=O)C)C1=CC=CC=C1 KCHQXPGUJBVNTN-UHFFFAOYSA-N 0.000 description 3
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- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 3
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- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 229910052755 nonmetal Inorganic materials 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
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- 238000000206 photolithography Methods 0.000 description 1
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- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical group [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
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- 229910006400 μ-Cl Inorganic materials 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
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- 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
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- 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
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- 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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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| TW101121395A TWI626243B (zh) | 2011-06-14 | 2012-06-14 | 包含氮雜苯并咪唑碳烯配位體的金屬錯合物及其於ｏｌｅｄ中的用途 |
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| ES2525757T3 (es) | 2009-12-14 | 2014-12-30 | Basf Se | Complejos metálicos que contienen ligandos de diazabencimidazolcarbeno y su uso en OLED |
| KR102090916B1 (ko) * | 2011-06-14 | 2020-03-19 | 유디씨 아일랜드 리미티드 | 아자벤즈이미다졸 카르벤 리간드를 포함하는 금속 착물 및 oled 에서의 이의 용도 |
| JP6080848B2 (ja) | 2011-08-12 | 2017-02-15 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | カルバゾロカルバゾール−ビス（ジカルボキシミド）及びその半導体としての使用 |
| EP2897959B1 (en) | 2012-09-20 | 2017-12-20 | UDC Ireland Limited | Azadibenzofurans for electronic applications |
| KR20140071732A (ko) * | 2012-12-04 | 2014-06-12 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| US10374172B2 (en) | 2013-03-20 | 2019-08-06 | Udc Ireland Limited | Azabenzimidazole carbene complexes as efficiency booster in OLEDs |
| TWI736512B (zh) | 2013-07-02 | 2021-08-21 | 愛爾蘭商Ｕｄｃ愛爾蘭責任有限公司 | 用於有機發光二極體之單取代二氮雜苯并咪唑碳烯金屬錯合物 |
| WO2015014835A1 (en) * | 2013-07-31 | 2015-02-05 | Basf Se | Luminescent diazabenzimidazole carbene metal complexes |
| EP3063153B1 (en) | 2013-10-31 | 2018-03-07 | Idemitsu Kosan Co., Ltd. | Azadibenzothiophenes for electronic applications |
| US10347851B2 (en) | 2013-12-20 | 2019-07-09 | Udc Ireland Limited | Highly efficient OLED devices with very short decay times |
| KR102330660B1 (ko) * | 2014-03-31 | 2021-11-24 | 유디씨 아일랜드 리미티드 | o-치환된 비-사이클로메탈화 아릴 그룹을 갖는 카르벤 리간드를 포함하는 금속 착체 및 유기 발광 다이오드에서의 이의 용도 |
| EP3174885B1 (en) | 2014-07-28 | 2019-10-02 | Idemitsu Kosan Co., Ltd. | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
| EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
| JP6491315B2 (ja) | 2014-08-08 | 2019-03-27 | ユー・ディー・シー アイルランド リミテッド | 電界発光イミダゾキノキサリンカルベン金属錯体 |
| EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
| KR102308117B1 (ko) | 2014-10-17 | 2021-10-01 | 삼성전자주식회사 | 카바졸계 화합물 및 이를 포함한 유기 발광 소자 |
| EP3015469B1 (en) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications |
| WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
| US10424746B2 (en) | 2014-11-18 | 2019-09-24 | Udc Ireland Limited | Pt- or Pd-carbene complexes for use in organic light emitting diodes |
| GB201421390D0 (en) * | 2014-12-02 | 2015-01-14 | Univ St Andrews | Luminescent complexes for OLEDs |
| EP3034506A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-functionalized carbazole derivatives for electronic applications |
| EP3034507A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs) |
| US10418569B2 (en) | 2015-01-25 | 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 |
| GB2535476A (en) * | 2015-02-16 | 2016-08-24 | Cambridge Display Tech Ltd | Compound, composition and organic light-emitting device |
| EP3061759B1 (en) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrile substituted dibenzofurans |
| CN107406473B (zh) | 2015-03-10 | 2020-06-16 | 国立研究开发法人产业技术综合研究所 | 杂配铱络合物、与使用该化合物的发光材料及有机发光元件 |
| EP3070144B1 (en) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
| EP3072943B1 (en) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazole-substituted benzonitriles |
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- 2012-06-12 CN CN201280039588.0A patent/CN103732603B/zh active Active
- 2012-06-12 KR KR1020147000925A patent/KR101950460B1/ko active Active
- 2012-06-12 CN CN201710301483.2A patent/CN107501330A/zh active Pending
- 2012-06-14 TW TW106103305A patent/TWI626296B/zh active
- 2012-06-14 TW TW101121395A patent/TWI626243B/zh active
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2017
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050260447A1 (en) * | 2004-05-18 | 2005-11-24 | Jason Brooks | Cyclometallated iridium carbene complexes for use as hosts |
| TW201241002A (en) * | 2011-03-08 | 2012-10-16 | Universal Display Corp | Pyridyl carbene phosphorescent emitters |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103732603B (zh) | 2017-05-31 |
| JP6300722B2 (ja) | 2018-03-28 |
| JP2014523874A (ja) | 2014-09-18 |
| TW201307367A (zh) | 2013-02-16 |
| CN107501330A (zh) | 2017-12-22 |
| EP2721043A4 (en) | 2015-02-25 |
| TW201736572A (zh) | 2017-10-16 |
| KR101950460B1 (ko) | 2019-02-20 |
| JP2018024696A (ja) | 2018-02-15 |
| KR20140041732A (ko) | 2014-04-04 |
| JP6584474B2 (ja) | 2019-10-02 |
| EP2721043A1 (en) | 2014-04-23 |
| EP3415521A1 (en) | 2018-12-19 |
| CN103732603A (zh) | 2014-04-16 |
| KR102090916B1 (ko) | 2020-03-19 |
| EP2721043B1 (en) | 2018-08-29 |
| TWI626243B (zh) | 2018-06-11 |
| WO2012172482A1 (en) | 2012-12-20 |
| KR20190020835A (ko) | 2019-03-04 |
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