WO2012163471A1 - Metallkomplexe - Google Patents
Metallkomplexe Download PDFInfo
- Publication number
- WO2012163471A1 WO2012163471A1 PCT/EP2012/002013 EP2012002013W WO2012163471A1 WO 2012163471 A1 WO2012163471 A1 WO 2012163471A1 EP 2012002013 W EP2012002013 W EP 2012002013W WO 2012163471 A1 WO2012163471 A1 WO 2012163471A1
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- Prior art keywords
- atoms
- group
- formula
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- 229910052751 metal Inorganic materials 0.000 title abstract description 31
- 239000002184 metal Substances 0.000 title abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims description 115
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 62
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 239000003446 ligand Substances 0.000 claims description 28
- 239000011159 matrix material Substances 0.000 claims description 26
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000002950 monocyclic group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 17
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000003367 polycyclic group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- 239000010931 gold Substances 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 229910052741 iridium Inorganic materials 0.000 claims description 9
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 239000010948 rhodium Substances 0.000 claims description 6
- 229910052737 gold Inorganic materials 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 230000005669 field effect Effects 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 57
- 150000003254 radicals Chemical class 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 208000027386 essential tremor 1 Diseases 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000000463 material Substances 0.000 description 29
- 101100489923 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) ABF2 gene Proteins 0.000 description 27
- 101150096395 him-1 gene Proteins 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- -1 heteroaromatic hydrocarbon radical Chemical class 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 0 CC(N(*)C1N)=C(*)N1[Al]=I Chemical compound CC(N(*)C1N)=C(*)N1[Al]=I 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000000260 fractional sublimation Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 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 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 101100537098 Mus musculus Alyref gene Proteins 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 101150095908 apex1 gene Proteins 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 3
- 150000003057 platinum Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- RRWFUWRLNIZICP-UHFFFAOYSA-N 1-bromo-2-phenoxybenzene Chemical compound BrC1=CC=CC=C1OC1=CC=CC=C1 RRWFUWRLNIZICP-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- SOQIDYYUSMPIDR-UHFFFAOYSA-N 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC=N1 SOQIDYYUSMPIDR-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229910004664 Cerium(III) chloride Inorganic materials 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 101100269674 Mus musculus Alyref2 gene Proteins 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- KRLBTHCAZSDQCI-UHFFFAOYSA-N anthracene-1,10-dione Chemical compound C1=CC=C2C=C3C(=O)C=CC=C3C(=O)C2=C1 KRLBTHCAZSDQCI-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- GHPOMFOMBISJGM-UHFFFAOYSA-N dimethyl 2-bromobenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1Br GHPOMFOMBISJGM-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
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- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMLDUMMLRZFROX-UHFFFAOYSA-N pyridin-2-ylboronic acid Chemical compound OB(O)C1=CC=CC=N1 UMLDUMMLRZFROX-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/12—Gold compounds
-
- 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
- C07F15/0086—Platinum compounds
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- 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
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- 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
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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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
- C09K2211/1029—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
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- 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
- H10K85/60—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
-
- 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
Definitions
- the present invention relates to metal complexes which are suitable for use as emitters in organic electroluminescent devices.
- OLEDs organic electroluminescent devices
- OLEDs organic electroluminescent devices
- Metal-organic complexes which exhibit phosphorescence instead of fluorescence are frequently used as emitting materials (M.A. Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6).
- organometallic compounds for quantum mechanical reasons, up to four times energy and power efficiency is possible using organometallic compounds as phosphorescence emitters. In general, there are still room for improvement in OLEDs that exhibit triplet emission, especially with regard to efficiency, operating voltage and service life.
- iridium or platinum complexes are used in phosphorescent OLEDs as triplet emitters in particular.
- An improvement of the platinum complexes used can be achieved by using metal complexes with tetradentate ligands, whereby the complexes have a higher thermal stability (WO 2004/108857, WO 2005/042550, WO 2005/042444).
- thermal stability WO 2004/108857, WO 2005/042550, WO 2005/042444.
- there is further need for improvement in platinum complexes particularly with regard to thermal stability, efficiency, lifetime and / or operating voltage.
- the object of the present invention is therefore to provide new metal complexes which are suitable as emitters for use in OLEDs.
- the invention relates to a compound according to formula (1),
- M is a transition metal
- A is N, P, B, C " or CR
- Y is the same or different CR 2 , NR, O, S or a single bond at each instance, with at most one group Y representing a single bond;
- Z is the same or different C or N on each occurrence, with the proviso that both Z are C when Ar 3 is an aromatic or heteroaromatic six-membered ring and either Z is C or Z is C and the other Z is N when Ar 3 is a heteroaromatic five-membered ring;
- D is the same or different C or N at each occurrence
- Aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms which may be substituted by one or more radicals R 3 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 3 , or a Diarylaminooeuvre, Diheteroaryl- amino group or Arylheteroarylaminoè having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 3 ;
- two or more adjacent radicals R 3 may together form a mono- or polycyclic aliphatic ring system; is identical or different at each occurrence H, D, F or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H atoms may be replaced by F; two or more substituents R 3 may also together form a mono- or polycyclic, aliphatic ring system.
- Structure is a structure in which Ar 3 is an aromatic six-membered ring, and the structure shown in b) is a structure in which Ar 3 is a heteroaromatic five-membered ring.
- An aryl group for the purposes of this invention contains 6 to 40 carbon atoms;
- a heteroaryl group contains 2 to 40 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
- the heteroatoms are preferably selected from N, O and / or S.
- aryl group or heteroaryl either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc., understood.
- An aromatic ring system in the sense of this invention contains 6 to 60 carbon atoms in the ring system.
- a heteroaromatic ring system in the sense of this invention contains 1 to 60 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
- the heteroatoms are preferably selected from N, O and / or S.
- An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups Heteroaryl groups by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as.
- a C, N or O atom or a carbonyl group may be interrupted.
- systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc.
- aromatic ring systems in the context of this invention, and also systems in which two or more aryl groups, for example by a linear or cyclic alkyl group or interrupted by a silyl group.
- biphenyl or terphenyl also be understood as an aromatic or heteroaromatic ring system.
- a cyclic alkyl, alkoxy or thioalkoxy group is understood as meaning a monocyclic, a bicyclic or a polycyclic group.
- a C 1 - to C 4 -alkyl group in which individual H atoms or CH 2 groups may be substituted by the abovementioned groups, for example the radicals methyl, ethyl, n-propyl, i Propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, tert-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n -Hexyl, s -hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl
- Pentenyl cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
- alkynyl group is meant, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
- a C to C 40 alkoxy group is understood as meaning, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
- an aromatic or heteroaromatic ring system having 5-60 aromatic ring atoms which may be substituted in each case with the abovementioned radicals R and which may be linked via any position on the aromatic or heteroaromatic, are understood, for example, groups which are derived from benzene, Naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene,
- adjacent radicals are radicals which are either bonded to the same atom, for example the radicals R, when the group Y is CR 2 , or radicals which are bonded to atoms which are bonded directly to one another.
- adjacent aryl or heteroaryl groups Ar 1 and Ar 2 are meant aryl or heteroaryl groups Ar 1 and Ar 2 which are bonded directly to one another.
- the radicals are as defined above, and two radicals each bind to one another with formal cleavage of a hydrogen atom.
- the radicals are alkyl groups, for example, the formation of a fused cycloalkyl group is possible. If the radicals are vinyl groups or a vinyl group and a
- Hydrogen atom is, for example, the formation of a condensed aryl group is possible. If the radicals R or R 1 form a ring system, then it is preferably a five-membered ring or a six-membered ring.
- the charge of the ligand is given by the number of coordinating carbon atoms, each having a negative charge, and optionally by the group A, when this group is C ⁇ .
- the metal M is selected from the group consisting of platinum, palladium, nickel, rhodium, iridium and gold.
- the metal M is selected from the group consisting of platinum, palladium, nickel, rhodium, iridium and gold.
- Pt (II), Ir (I) and Au (III are particularly preferred.
- both groups D in the groups Ar 1 for N and both groups D in the groups Ar 2 are C, or both groups D in the groups Ar 1 are C and both groups D in the groups Ar 2 are N ,
- A is N or P, particularly preferably N.
- M is Pt (II)
- Y is the same or different at each occurrence for CR 2 or for a single bond, with at most one group Y being a single bond. More preferably, Y is the same or different at each occurrence for CR 2 .
- both bridges Y are chosen equal.
- Ar is selected from the structures of the following formulas (3), (4) and (5),
- Formula (3) Formula (4) Formula (5) wherein X is the same or different at each occurrence of CR 1 or N or wherein two adjacent groups X in formula (3) together represent NR, O or S and the other group X is CR 1 or N; * indicates binding to Yan and # indicates binding to A.
- Particularly preferred groups Ar 3 are structures of the formula (3).
- X is identical or different at each occurrence for CR 1 .
- the partial ligands A ⁇ -Ar 2 bidentate monoanionic
- Ligands having with the transition metal M a cyclometa-connected five-membered ring with at least one metal-carbon bond are, in particular, ligands such as are generally used in the field of phosphorescent metal complexes for organic electroluminescent devices, ie phenylpyndin, naphthylpyridine ligands, Phenylquinoline, phenylisoquinoline, etc., which may be substituted by one or more radicals R 1 .
- the group Ar 1 is preferably in each case one of the following groups (6) to (16) and as
- Each group Ar 2 has one of the following groups (17) to (38).
- the groups are preferably selected such that one of the groups Ar 1 or Ar 2 in the partial ligand A ⁇ -Ar 2 binds via a neutral nitrogen atom or a carbene carbon atom and the other of the groups Ar 1 or Ar 2 in the partial ligands A 1 -Ar 2 binds via a negatively charged carbon atom or a negatively charged nitrogen atom.
- Suitable structures Ar 1 are thus the structures of the following formulas (6) to (16),
- Suitable structures Ar 2 are the structures of the following formulas (17) to (38),
- X in the formulas (6) to (38) at each occurrence is the same or different for CR 1 or N
- V is the same or different at each occurrence as O
- S or NR 1 and R has the same meaning as described above.
- a maximum of three symbols X in each group represent N, more preferably, at most two symbols X in each group represent N, most preferably, a symbol X in each group represents N.
- all symbols X stand for
- two residues on adjacent groups Ar and Ar 2 may also form a ring with each other.
- This can also give rise to a new aryl or heteroaryl group, so that Ar 1 and Ar 2 are no longer separate aryl groups.
- radicals R 1 are identically or differently selected on each occurrence from the group consisting of H, D, F, N (R 2 ) 2 , a straight-chain alkyl group having 1 to 6 C atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, each of which may be substituted by one or more radicals R 2 ; in this case, two adjacent radicals R or R with R 1 can also form a mono- or polycyclic aliphatic ring system with one another.
- the group R is preferably identical or different at each occurrence for an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, which may be substituted by one or more radicals R 2 , and which is preferred contains no condensed aryl or heteroaryl groups.
- the group R is preferably H, D, a straight-chain alkyl group having 1 to 10 C atoms or an alkenyl or alkynyl group having 2 to 10 C atoms.
- Atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, each with one or more Radicals R 2 may be substituted, wherein one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, which may be substituted by one or more radicals R 2 and which are preferred does not contain condensed aryl or heteroaryl groups;
- two or more radicals R which bind to the same carbon atom, together with one another form a mono- or polycyclic, aliphatic or aromatic ring system.
- radicals R at each occurrence are identically or differently selected from the group consisting of H, a straight-chain alkyl group having 1 to 5 C atoms, in particular methyl, or a branched or cyclic alkyl group having 3 to 5 C atoms, in particular iso- Propyl or tert-butyl, wherein one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 12 aromatic ring atoms, each of which may be substituted by one or more radicals R 2 ; thereby two remainders R, which at the same
- Bind carbon atom also form a mono- or polycyclic, aliphatic or aromatic ring system with each other.
- the bonds shown in dashed lines represent the bond of the group to Ar 1 and Ar 3 .
- the abovementioned preferred embodiments can be combined with one another as desired. In a particularly preferred embodiment of the invention, the abovementioned preferred embodiments apply simultaneously. In a preferred embodiment of the invention, therefore, for the compounds of the formula (1):
- M is selected from the group consisting of platinum, palladium,
- Nickel, rhodium, iridium and gold especially Pt (II), Pd (II), Ni (II), Rh (I), Ir (I) and Au (III);
- D is the same or different C or N at each occurrence, where two groups D are N and the other two groups D are C;
- A is N or P
- Y is the same or different at each instance of CR 2 or a single bond, with at most one group Y being a single bond;
- Ar 3 is selected from the above structures of formulas (3), (4) or (5);
- Ar 1 is selected from the above structures of formulas (6) to (16);
- Ar 2 is selected from the above structures of formulas (17) to (38);
- M is selected from the group consisting of Pt (II), Ir (I) and Au (III), in particular Pt (II).
- D is equal to N in both groups Ar 1 and equal to C in both groups Ar 2 or is equal to C in both groups Ar 1 and equal to N in both groups Ar 2 ;
- A is N;
- Y is CR2 at each occurrence, and both groups Y are the same;
- Ar 3 is selected from the above structures of formula (3);
- Ar 1 is selected from the above structures of formulas (6) to (16);
- Ar 2 is selected from the above structures of formulas (17) to (38);
- the ligands of the compounds of the invention can be prepared according to Scheme 1.
- the dibromide 1 can be converted to 2 by Suzuki coupling. Reaction of 2 via Ullmann coupling with 2-halo-isophthalates and subsequent acidic cyclization leads to bisketone 5, which by reduction with hydrazine hydrate or BH 3 x THF to ligand. 7 can be implemented. An addition of suitable aryllithium or aryl-magnesium compounds and subsequent acid cyclization of the diol intermediately formed leads to type 6 ligands. Type 4 ligands can be obtained from 3 by cerium-mediated Grignard addition and subsequent cyclization of the diol intermediately formed. Of course, these structures may also have further substituents. Further functionalization of the type 4, 6 and 7 ligands is possible by Scheme 2 via halogenation and CC or CN coupling.
- X single bond, CR 2 , O, S, etc.
- Ar 2-N-heteroarylboronic acids such as 2-pyridineboronic acid
- the complexation of the type 4, 6, 7, 15, 16, and 17 ligands to the complexes of the invention can be carried out as shown in Scheme 4 on Type 4 ligands, although other Pt precursors can be used quite similarly.
- the metal complexes according to the invention can in principle be prepared by various processes in which the ligand is reacted with a suitable metal precursor. Therefore, another object of the present invention is a process for the preparation of the compounds of formula (1) by reacting the corresponding free ligand with a suitable metal compound.
- Suitable platinum starting materials are, for example, PtCl 2 , K 2 [PtCl 4 ], PtCl 2 (DMSO) 2 , Pt (Me) 2 (DMSO) 2 ,
- Suitable iridium starting materials are, for example, iridium (III) chloride hydrate, iridium-olefin complexes, for example with COD as ligand, Ir (acac) 3, Ir (tBu-acac) 3 or Vaskas complex.
- Suitable gold starting materials are, for example, AuCl 3 or HAuCl 4 .
- the synthesis can also be activated thermally, photochemically and / or by microwave radiation.
- the reaction is carried out without the use of an additional solvent in the melt.
- melt means that the ligand has melted and the metal precursor is dissolved or suspended in this melt
- the corresponding free ligand is reacted with the metal precursor, for example K 2 PtCl, in glacial acetic acid.
- the compounds of the invention according to formula (1) can be obtained in high purity, preferably more than 99% (determined by means of 1 H-NMR and / or HPLC).
- the compounds according to the invention can also be made soluble by suitable substitution, for example by longer alkyl groups (about 4 to 20 C atoms), in particular branched alkyl groups, or optionally substituted aryl groups, for example xylyl, mesityl or branched terphenyl or quaterphenyl groups.
- suitable substitution for example by longer alkyl groups (about 4 to 20 C atoms), in particular branched alkyl groups, or optionally substituted aryl groups, for example xylyl, mesityl or branched terphenyl or quaterphenyl groups.
- Such compounds are then soluble in common organic solvents, such as toluene or xylene at room temperature in sufficient concentration to process the complexes from solution can.
- These soluble compounds are particularly suitable for processing from solution, for example by printing processes.
- Another object of the present invention is therefore a
- Formulation in particular a solution, a suspension or a miniemulsion containing at least one compound according to formula (1) and at least one solvent.
- Yet another object of the present invention is a mixture containing at least one compound according to formula (1) and at least one further compound, in particular a further A compound which is suitable as matrix material for the compound according to formula (1).
- An electronic device is understood to mean a device which contains anode, cathode and at least one layer, this layer containing at least one organic or organometallic compound.
- the electronic device according to the invention thus contains anode, cathode and at least one layer which contains at least one compound of the above-mentioned formula (1).
- preferred electronic devices are selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light-emitting Transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs) or organic laser diodes (O-lasers) in at least one layer at least one compound according to the above-mentioned formula (1). Particularly preferred are organic electroluminescent devices.
- Active components are generally the organic or inorganic materials incorporated between the anode and cathode, for example, charge injection, charge transport or charge blocking materials, but especially emission materials and matrix materials.
- the compounds according to the invention exhibit particularly good properties as emission material in organic electroluminescent devices.
- a preferred embodiment of the invention are therefore organic electroluminescent devices.
- the organic electroluminescent device includes cathode, anode and at least one emitting layer. Apart from these layers, they may also contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, charge generation layers and / or organic or inorganic p / n junctions. Likewise, interlayers may be introduced between two emitting layers which, for example, have an exciton-blocking function and / or control the charge balance in the electroluminescent device. It should be noted, however, that not necessarily each of these layers must be present.
- the organic electroluminescent device can be any organic electroluminescent device.
- the organic electroluminescent device can be any organic electroluminescent device.
- various emitting compounds are used which can fluoresce or phosphoresce. Particular preference is given to three-layer systems, the three layers exhibiting blue, green and orange or red emission (for the basic structure see, for example, WO 2005/011013) or systems having more than three emitting layers. It may also be a hybrid system wherein one or more layers fluoresce and one or more other layers phosphoresce.
- the organic electroluminescent device contains the compound of the formula (1) or the preferred embodiments listed above as the emitting compound in one or more emitting layers.
- the compound according to formula (1) When the compound according to formula (1) is used as the emitting compound in an emitting layer, it is preferably used in combination with one or more matrix materials.
- Mixture of the compound according to formula (1) and the matrix material contains between 0.1 and 99 vol.%, Preferably between 1 and 90 vol.%, Particularly preferably between 3 and 40 vol.%, In particular between 5 and 15 vol. -% of the compound according to formula (1) based on the total mixture of emitter and matrix material.
- Corresponding contains the mixture between 99.9 and 1 vol .-%, preferably between 99 and 10 vol .-%, more preferably between 97 and 60 vol .-%, in particular between 95 and 85 vol .-% of the matrix material based on the total mixture of emitter and matrix material.
- matrix material it is generally possible to use all materials known for this purpose according to the prior art.
- the triplet level of the matrix material is higher than the triplet level of the emitter.
- Suitable matrix materials for the compounds according to the invention are ketones, phosphine oxides, sulfoxides and sulfones, for. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO
- a plurality of different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material.
- a preferred combination is, for example, the use of an aromatic ketone, a triazine derivative or a phosphine oxide derivative with a triarylamine derivative or a carbazole derivative as a mixed one Matrix for the metal complex according to the invention.
- Also preferred is the use of a mixture of a charge-transporting matrix material and an electrically inert matrix material, which is not or not significantly involved in charge transport, such. As described in WO 2010/108579.
- the triplet emitter with the shorter-wave emission spectrum serves as a co-matrix for the triplet emitter with the longer-wave emission spectrum.
- the complexes according to the invention of formula (1) can be used as a co-matrix for longer-wave emitting triplet emitters, for example for green or red emitting triplet emitters.
- the compounds according to the invention can also be used in other functions in the electronic device, for example as hole transport material in a hole injection or transport layer, as charge generation material or as electron blocking material.
- the complexes according to the invention can be used as matrix material for other phosphorescent metal complexes in an emitting layer.
- low work function metals, metal alloys or multilayer structures of various metals are preferable, such as alkaline earth metals, alkali metals, main group metals or lanthanides (eg, Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.).
- alkaline earth metals alkali metals, main group metals or lanthanides (eg, Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.).
- alloys of an alkali or alkaline earth metal and silver for example an alloy of magnesium and silver.
- further metals which have a relatively high work function such as, for example, B. Ag, which then usually combinations of metals, such as Mg / Ag, Ca / Ag or Ba / Ag are used.
- a metallic cathode and the organic semiconductor may also be preferred to introduce between a metallic cathode and the organic semiconductor a thin intermediate layer of a material with a high dielectric constant.
- a material with a high dielectric constant come alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (eg LiF, Li 2 O, BaF 2> MgO, NaF, CsF, CS 2 CO 3, etc.).
- organic alkali metal complexes for.
- the layer thickness of this layer is preferably between 0.5 and 5 nm.
- the anode materials with a high work function are preferred.
- the anode has a work function greater than 4.5 eV. Vacuum up.
- metals with a high redox potential such as Ag, Pt or Au
- electrodes z. B. AI / Ni / NiO, AI / PtO x
- metal / metal oxide may be preferred, metal / metal oxide.
- at least one of the electrodes must be transparent or partially transparent in order to allow either the irradiation of the organic material (O-SC) or the extraction of light (OLED / PLED, O-LASER).
- Preferred anode materials here are conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO).
- conductive, doped organic materials in particular conductive doped polymers, for. B. PEDOT, PANI or derivatives of these polymers.
- the device is structured accordingly (depending on the application), contacted and finally hermetically sealed because the life of such devices drastically shortened in the presence of water and / or air.
- an organic electroluminescent device characterized in that one or more layers are coated with a sublimation process. In this case, 6 mbar, the materials in vacuum sublimation at an initial pressure of usually less than 10 "5 mbar, preferably less than 10" evaporated. It is also possible that the initial pressure is even lower or even higher, for example less than 10 "7 mbar.
- an organic electroluminescent device characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation.
- the materials are applied at a pressure between 10 ⁇ 5 mbar and 1 bar.
- OVJP Organic Vapor Jet Printing
- the materials are applied directly through a nozzle and thus structured (for example, BMS Arnold et al., Appl. Phys. Lett., 2008, 92, 053301).
- an organic electroluminescent device characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such.
- any printing process such as screen printing, flexographic printing, offset printing or Nozzle printing, but more preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (inkjet printing), are produced.
- LITI Light Induced Thermal Imaging, thermal transfer printing
- ink-jet printing inkjet printing
- the organic electroluminescent device may also be fabricated as a hybrid system by applying one or more layers of solution and depositing one or more other layers.
- an emitting layer containing a compound of formula (1) and a solution matrix material and then vacuum evaporate a hole blocking layer and / or an electron transport layer.
- Organic electroluminescent devices containing compounds according to formula (1) as emitting materials have a very good lifetime.
- Organic electroluminescent devices containing compounds according to formula (1) as emitting materials have excellent efficiency.
- the metal complexes according to the invention make it possible to obtain organic electroluminescent devices which phosphoresce in the blue color range.
- blue phosphorescence according to the prior art is very difficult to realize with good efficiencies and lifetimes.
- the metal complexes of the invention are synthetically good and accessible in high yield.
- Brackets for literature-known chemical compounds refer to the CAS number.
- a suspension of 54.2 g (220 mmol) of anhydrous cerium (III) chloride and 100 g of glass beads (5 mm diameter) in 300 ml of THF is stirred for 1 h.
- 51.9 g (100 mmol) of S25 are then added in portions and the mixture is again stirred at room temperature for 1 h.
- the suspension is cooled to 0 ° C and slowly added dropwise 600 ml (600 mmol) of a 1 N methylmagnesium chloride in THF, so that the temperature does not exceed 5 ° C. After completion of the addition, allowed to warm to room temperature and stirred for 16 h.
- reaction mixture is cooled again to 0 ° C., carefully hydrolysed (exothermic, gas evolution!)
- 1000 ml of 1 N acetic acid 1000 ml of ethyl acetate are added, the organic phase is separated off and the aqueous phase is extracted three times with each time 200 ml of ethyl acetate, the combined organic phases are washed twice with 300 ml of water, once with 500 ml of saturated brine, dried over sodium sulfate and then the solvent is removed in vacuo.
- a suspension of 54.2 g (220 mmol) of anhydrous cerium (III) chloride and 100 g of glass beads (5 mm diameter) in 400 ml of THF is stirred for 1 h.
- 51.6 g (100 mmol) of S9 are added in portions to solid and stirred again for 1 h at room temperature.
- the suspension is cooled to 0 ° C and slowly added dropwise 600 ml (600 mmol) of a 1 N methylmagnesium chloride in THF, so that the temperature does not exceed 5 ° C. After completion of the addition, allow to warm to room temperature and stirred for 16 h.
- reaction mixture is cooled again to 0 ° C., carefully hydrolyzed (exothermic, gas evolution!)
- 650 ml of 1N acetic acid 1000 ml of ethyl acetate are added, the organic phase is separated off and the aqueous phase is extracted three times with 200 ml each time Ethyl acetate, the combined organic phases are washed twice with 300 ml of water and once with 500 ml of saturated sodium chloride solution, dried over sodium sulfate and then the solvent is removed in vacuo.
- the residue is taken up in 300 ml of methanesulfonic acid, 100 g of polyphosphoric acid are added, the mixture is slowly heated to 120 ° C. and stirred for a further 4 hours.
- Extractant concentrated in vacuo to about 100 ml.
- Metal complexes which have too good solubility in the extractant are brought to crystallization by the dropwise addition of 200 ml of methanol.
- the solid of the suspension thus obtained is filtered off, washed once with about 50 ml of methanol and dried. After drying, the purity of the metal complex is determined by NMR and / or HPLC. If the purity is below 99.5%, the hot extraction step is repeated; is reached a purity of 99.5 - 99.9%, the Pt complex is sublimated.
- the sublimation is carried out in a high vacuum (p about 10 "6 mbar) in the temperature range of about 350 to about 390 ° C, the sublimation is preferably carried out in the form of a fractional sublimation.
- inventive OLEDs and OLEDs according to the prior art is carried out according to a general method according to WO 2004/058911, based on the circumstances described here
- the OLEDs have in principle the following layer structure: substrate / optional hole injection layer (HIL1) / hole injection layer (HIL2) / hole transport layer (HTL) / electron blocker layer (EBL) / emission layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) and finally a cathode ,
- HIL1 hole injection layer
- HIL2 hole injection layer
- HTL hole transport layer
- EBL electron blocker layer
- EML emission layer
- ETL optional hole blocking layer
- ETL optional hole blocking layer
- ETL electron transport layer
- the emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter), which is added to the matrix material or the matrix materials by co-evaporation in a certain volume fraction.
- the electron transport layer may consist of a mixture of two materials.
- the exact structure of the OLEDs is shown in Table 1.
- the materials used to make the OLEDs are shown in Table 3.
- the OLEDs are characterized by default.
- the electroluminescence spectra, the current efficiency (measured in cd / A) and the voltage (measured at 1000 cd / m 2 in V) are determined from current-voltage-brightness characteristics (IUL characteristic curves).
- IUL characteristic curves current-voltage-brightness characteristics
- the service life is determined.
- the lifetime is defined as the time after which the luminance has dropped to a certain level from a certain starting luminance.
- the term LD50 means that the said lifetime is the time at which the luminance has dropped to 50% of the starting luminance, ie from 4000 cd / m 2 to 2000 cd / m 2 .
- the values for the lifetime can be converted to an indication for other starting luminous densities with the aid of conversion formulas known to the person skilled in the art.
- the life for a starting luminous flux of 1000 cd / m 2 is a common statement.
- the compounds according to the invention can be used inter alia as phosphorescent emitter materials in the emission layer in OLEDs.
- the compounds according to the invention can be used inter alia as phosphorescent emitter materials in the emission layer in OLEDs.
- HIM1 HIM2 HTM M1 M2: Pt (Ref1) M1 ETM1: LiQ
- HIM1 HIM2 HTM M1 M2: PtL1 M1 ETM1: LiQ
- HIM1 HIM2 HTM M1 M2: PtL2 M1
- ETM1 LiQ
- the OLEDs are produced as described above.
- the OLEDs have the following structure:
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Abstract
Description
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Cited By (132)
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JP2013080898A (ja) * | 2011-09-22 | 2013-05-02 | Nippon Hoso Kyokai <Nhk> | 有機発光素子及びこれを用いた表示装置 |
WO2013077345A1 (ja) * | 2011-11-24 | 2013-05-30 | 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、並びに該有機電界発光素子を用いた発光装置、表示装置及び照明装置 |
WO2014015936A1 (en) * | 2012-07-23 | 2014-01-30 | Merck Patent Gmbh | Ligands and their preparation |
US20140084261A1 (en) * | 2012-09-25 | 2014-03-27 | Universal Display Corporation | Electroluminescent element |
WO2014047616A1 (en) * | 2012-09-24 | 2014-03-27 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Metal compounds, methods, and uses thereof |
KR20150095545A (ko) * | 2014-02-13 | 2015-08-21 | 에스에프씨 주식회사 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
WO2015192941A1 (de) | 2014-06-18 | 2015-12-23 | Merck Patent Gmbh | Zusammensetzungen für elektronische vorrichtungen |
US9224963B2 (en) | 2013-12-09 | 2015-12-29 | Arizona Board Of Regents On Behalf Of Arizona State University | Stable emitters |
WO2015197156A1 (de) | 2014-06-25 | 2015-12-30 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
US9238668B2 (en) | 2011-05-26 | 2016-01-19 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Synthesis of platinum and palladium complexes as narrow-band phosphorescent emitters for full color displays |
US9324957B2 (en) | 2010-04-30 | 2016-04-26 | Arizona Board Of Regents On Behalf Of Arizona State University | Synthesis of four coordinated gold complexes and their applications in light emitting devices thereof |
WO2016083914A1 (en) | 2014-11-26 | 2016-06-02 | Basf Se | 4-oxoquinoline compounds |
US9385329B2 (en) | 2013-10-14 | 2016-07-05 | Arizona Board of Regents on behalf of Arizona State University and Universal Display Corporation | Platinum complexes and devices |
US9382273B2 (en) | 2010-04-30 | 2016-07-05 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Synthesis of four coordinated palladium complexes and their applications in light emitting devices thereof |
EP3056504A1 (de) | 2015-02-16 | 2016-08-17 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US9425415B2 (en) | 2011-02-18 | 2016-08-23 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Four coordinated platinum and palladium complexes with geometrically distorted charge transfer state and their applications in light emitting devices |
EP3061763A1 (de) | 2015-02-27 | 2016-08-31 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
CN106029665A (zh) * | 2014-02-24 | 2016-10-12 | 巴斯夫欧洲公司 | 新的环吖嗪及其作为半导体的用途 |
EP3098229A1 (de) | 2015-05-15 | 2016-11-30 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3101021A1 (de) | 2015-06-01 | 2016-12-07 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2016198144A1 (en) | 2015-06-10 | 2016-12-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US9550801B2 (en) | 2009-04-06 | 2017-01-24 | Arizona Board Of Regents Acting For And On Behalf Of Arizona State University | Synthesis of four coordinated platinum complexes and their applications in light emitting devices thereof |
EP3124488A1 (de) | 2015-07-29 | 2017-02-01 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2017016630A1 (en) | 2015-07-30 | 2017-02-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US9617291B2 (en) | 2015-06-03 | 2017-04-11 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
EP3159350A1 (de) | 2015-09-03 | 2017-04-26 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2017071791A1 (en) | 2015-10-27 | 2017-05-04 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US9673409B2 (en) | 2013-06-10 | 2017-06-06 | Arizona Board Of Regents On Behalf Of Arizona State University | Phosphorescent tetradentate metal complexes having modified emission spectra |
US9711739B2 (en) | 2015-06-02 | 2017-07-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes containing indoloacridine and its analogues |
US9711741B2 (en) | 2012-08-24 | 2017-07-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal compounds and methods and uses thereof |
EP3205658A1 (de) | 2016-02-09 | 2017-08-16 | Universal Display Corporation | Organische elektrolumineszenzmaterialien und vorrichtungen |
EP3231809A2 (de) | 2016-04-11 | 2017-10-18 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US9818959B2 (en) | 2014-07-29 | 2017-11-14 | Arizona Board of Regents on behlaf of Arizona State University | Metal-assisted delayed fluorescent emitters containing tridentate ligands |
EP3261146A2 (de) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3261147A1 (de) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3270435A2 (de) | 2016-06-20 | 2018-01-17 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US9920242B2 (en) | 2014-08-22 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent materials as co-host materials for fluorescent OLEDs |
US9923155B2 (en) | 2014-07-24 | 2018-03-20 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) complexes cyclometalated with functionalized phenyl carbene ligands and their analogues |
EP3297051A1 (de) | 2016-09-14 | 2018-03-21 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3301088A1 (de) | 2016-10-03 | 2018-04-04 | Universal Display Corporation | Kondensierte pyridine als organische elektrolumineszente materialien und vorrichtungen |
US9941479B2 (en) | 2014-06-02 | 2018-04-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues |
EP3305796A1 (de) | 2016-10-07 | 2018-04-11 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3321258A1 (de) | 2016-11-09 | 2018-05-16 | Universal Display Corporation | 4-phenylbenzo[g]quinazolin oder 4-(3,5-dimethylphenylbenzo[g]quinazoline iridiumkomplexe zur verwendung als nah-infrarot oder infrarot emittierende materialien in oleds |
EP3323822A1 (de) | 2016-09-23 | 2018-05-23 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US10020455B2 (en) | 2014-01-07 | 2018-07-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues |
EP3345914A1 (de) | 2017-01-09 | 2018-07-11 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US10033003B2 (en) | 2014-11-10 | 2018-07-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate metal complexes with carbon group bridging ligands |
EP3354654A2 (de) | 2016-11-11 | 2018-08-01 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US10056567B2 (en) | 2014-02-28 | 2018-08-21 | Arizona Board Of Regents On Behalf Of Arizona State University | Chiral metal complexes as emitters for organic polarized electroluminescent devices |
EP3381927A1 (de) | 2017-03-29 | 2018-10-03 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3401318A1 (de) | 2017-05-11 | 2018-11-14 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3418286A1 (de) | 2017-06-23 | 2018-12-26 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US10177323B2 (en) | 2016-08-22 | 2019-01-08 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes and octahedral iridium complexes employing azepine functional groups and their analogues |
EP3444258A2 (de) | 2017-08-10 | 2019-02-20 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3489243A1 (de) | 2017-11-28 | 2019-05-29 | University of Southern California | Carbenverbindungen und organische elektrolumineszente vorrichtungen |
EP3492480A2 (de) | 2017-11-29 | 2019-06-05 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3492528A1 (de) | 2017-11-30 | 2019-06-05 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US10516117B2 (en) | 2017-05-19 | 2019-12-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emttters employing benzo-imidazo-phenanthridine and analogues |
EP3613751A1 (de) | 2018-08-22 | 2020-02-26 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2020053315A1 (de) | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Elektrolumineszierende vorrichtungen |
WO2020053314A1 (de) | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Elektrolumineszierende vorrichtungen |
WO2020053150A1 (en) | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP3689889A1 (de) | 2019-02-01 | 2020-08-05 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3690973A1 (de) | 2019-01-30 | 2020-08-05 | University Of Southern California | Organische elektrolumineszente materialien und vorrichtungen |
WO2020178230A1 (en) | 2019-03-04 | 2020-09-10 | Merck Patent Gmbh | Ligands for nano-sized materials |
EP3715353A1 (de) | 2019-03-26 | 2020-09-30 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US10793546B2 (en) | 2014-08-15 | 2020-10-06 | Arizona Board Of Regents On Behalf Of Arizona State University | Non-platinum metal complexes for excimer based single dopant white organic light emitting diodes |
WO2020208051A1 (en) | 2019-04-11 | 2020-10-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US10822363B2 (en) | 2016-10-12 | 2020-11-03 | Arizona Board Of Regents On Behalf Of Arizona State University | Narrow band red phosphorescent tetradentate platinum (II) complexes |
EP3750897A1 (de) | 2019-06-10 | 2020-12-16 | Universal Display Corporation | Organische elektrolumineszente materialien und geräte |
US10886476B2 (en) | 2017-10-24 | 2021-01-05 | Samsung Display Co., Ltd. | Polycyclic compound and organic electroluminescence device including the same |
EP3771717A1 (de) | 2019-07-30 | 2021-02-03 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3778614A1 (de) | 2019-08-16 | 2021-02-17 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US10930865B2 (en) | 2015-08-04 | 2021-02-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes, devices, and uses thereof |
US10964897B2 (en) | 2014-07-28 | 2021-03-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tridentate cyclometalated metal complexes with six-membered coordination rings |
US10991897B2 (en) | 2014-11-10 | 2021-04-27 | Arizona Board Of Regents On Behalf Of Arizona State University | Emitters based on octahedral metal complexes |
US10995108B2 (en) | 2012-10-26 | 2021-05-04 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal complexes, methods, and uses thereof |
EP3816175A1 (de) | 2019-11-04 | 2021-05-05 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2021089450A1 (en) | 2019-11-04 | 2021-05-14 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2021094269A1 (en) | 2019-11-12 | 2021-05-20 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2021110741A1 (en) | 2019-12-04 | 2021-06-10 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP3845545A1 (de) | 2020-01-06 | 2021-07-07 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3858945A1 (de) | 2020-01-28 | 2021-08-04 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2021151922A1 (de) | 2020-01-29 | 2021-08-05 | Merck Patent Gmbh | Benzimidazol-derivate |
US11101435B2 (en) | 2017-05-19 | 2021-08-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complexes based on biscarbazole and analogues |
WO2021191058A1 (en) | 2020-03-23 | 2021-09-30 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US11183670B2 (en) | 2016-12-16 | 2021-11-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light emitting diode with split emissive layer |
EP3937268A1 (de) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonische oleds und vertikale dipolstrahler |
US11329244B2 (en) | 2014-08-22 | 2022-05-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Organic light-emitting diodes with fluorescent and phosphorescent emitters |
US11335865B2 (en) | 2016-04-15 | 2022-05-17 | Arizona Board Of Regents On Behalf Of Arizona State University | OLED with multi-emissive material layer |
EP4001286A1 (de) | 2020-11-24 | 2022-05-25 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4001287A1 (de) | 2020-11-24 | 2022-05-25 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4016659A1 (de) | 2020-11-16 | 2022-06-22 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4019526A1 (de) | 2018-01-26 | 2022-06-29 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4039692A1 (de) | 2021-02-03 | 2022-08-10 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4053137A1 (de) | 2021-03-05 | 2022-09-07 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4056578A1 (de) | 2021-03-12 | 2022-09-14 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4060758A2 (de) | 2021-02-26 | 2022-09-21 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4059941A1 (de) | 2021-03-15 | 2022-09-21 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4059915A2 (de) | 2021-02-26 | 2022-09-21 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4074723A1 (de) | 2021-04-05 | 2022-10-19 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4075531A1 (de) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonische oleds und vertikale dipolstrahler |
EP4075530A1 (de) | 2021-04-14 | 2022-10-19 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4079743A1 (de) | 2021-04-23 | 2022-10-26 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4086266A1 (de) | 2021-04-23 | 2022-11-09 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4112701A2 (de) | 2021-06-08 | 2023-01-04 | University of Southern California | Molekulare ausrichtung homoleptischer iridiumphosphore |
US11594688B2 (en) | 2017-10-17 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Display and lighting devices comprising phosphorescent excimers with preferred molecular orientation as monochromatic emitters |
US11594691B2 (en) | 2019-01-25 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Light outcoupling efficiency of phosphorescent OLEDs by mixing horizontally aligned fluorescent emitters |
EP4151699A1 (de) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US11647643B2 (en) | 2017-10-17 | 2023-05-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Hole-blocking materials for organic light emitting diodes |
EP4185086A1 (de) | 2017-07-26 | 2023-05-24 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4212539A1 (de) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US11708385B2 (en) | 2017-01-27 | 2023-07-25 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emitters employing pyrido-pyrrolo-acridine and analogues |
EP4231804A2 (de) | 2022-02-16 | 2023-08-23 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4242285A1 (de) | 2022-03-09 | 2023-09-13 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US11785838B2 (en) | 2019-10-02 | 2023-10-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Green and red organic light-emitting diodes employing excimer emitters |
EP4265626A2 (de) | 2022-04-18 | 2023-10-25 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4282863A1 (de) | 2022-05-24 | 2023-11-29 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4293001A1 (de) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4299693A1 (de) | 2022-06-28 | 2024-01-03 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US11878988B2 (en) | 2019-01-24 | 2024-01-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Blue phosphorescent emitters employing functionalized imidazophenthridine and analogues |
EP4326030A1 (de) | 2022-08-17 | 2024-02-21 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US11930662B2 (en) | 2015-06-04 | 2024-03-12 | Arizona Board Of Regents On Behalf Of Arizona State University | Transparent electroluminescent devices with controlled one-side emissive displays |
US11945985B2 (en) | 2020-05-19 | 2024-04-02 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal assisted delayed fluorescent emitters for organic light-emitting diodes |
EP4362631A2 (de) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4362645A2 (de) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4362630A2 (de) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4369898A1 (de) | 2022-10-27 | 2024-05-15 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2024105066A1 (en) | 2022-11-17 | 2024-05-23 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP4376583A2 (de) | 2022-10-27 | 2024-05-29 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4386065A1 (de) | 2022-12-14 | 2024-06-19 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US12037348B2 (en) | 2018-03-09 | 2024-07-16 | Arizona Board Of Regents On Behalf Of Arizona State University | Blue and narrow band green and red emitting metal complexes |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102077994B1 (ko) | 2011-09-21 | 2020-02-17 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 카르바졸 유도체 |
EP2780325B1 (de) | 2011-11-17 | 2016-02-03 | Merck Patent GmbH | Spiro-dihydroacridinderivate und ihre verwendung als materialien für organische elektrolumineszenzvorrichtungen |
JP2017538284A (ja) * | 2014-10-17 | 2017-12-21 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 複数のホスト材料及びそれを含む有機電界発光デバイス |
KR102486392B1 (ko) * | 2017-11-24 | 2023-01-09 | 삼성전자주식회사 | 유기 발광 소자 및 이의 제조 방법 |
KR20200061483A (ko) * | 2018-11-23 | 2020-06-03 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함하는 유기 발광 소자 |
CN109456326A (zh) * | 2018-12-10 | 2019-03-12 | 苏州大学 | 有机电致发光器件、羰基桥连的三芳胺衍生物及其应用 |
KR20200077673A (ko) * | 2018-12-20 | 2020-07-01 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
US20200388774A1 (en) * | 2019-02-22 | 2020-12-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20210014834A (ko) * | 2019-07-30 | 2021-02-10 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
KR20210018574A (ko) | 2019-08-05 | 2021-02-18 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
CN112993199B (zh) * | 2021-02-25 | 2023-03-07 | 上海弗屈尔光电科技有限公司 | 一种三元组合物及含有该组合物的有机发光元件与应用 |
Citations (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
EP0652273A1 (de) | 1993-11-09 | 1995-05-10 | Shinko Electric Industries Co. Ltd. | Organisches Material für elektrolumineszente Vorrichtung und elektrolumineszente Vorrichtung |
EP0676461A2 (de) | 1994-04-07 | 1995-10-11 | Hoechst Aktiengesellschaft | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
WO1998027136A1 (de) | 1996-12-16 | 1998-06-25 | Aventis Research & Technologies Gmbh & Co Kg | ARYLSUBSTITUIERTE POLY(p-ARYLENVINYLENE), VERFAHREN ZUR HERSTELLUNG UND DEREN VERWENDUNG IN ELEKTROLUMINESZENZBAUELEMENTEN |
EP1205527A1 (de) | 2000-03-27 | 2002-05-15 | Idemitsu Kosan Co., Ltd. | Organische elektrolumineszierende vorrichtung |
WO2004013080A1 (en) | 2002-08-01 | 2004-02-12 | Covion Organic Semiconductors Gmbh | Spirobifluorene derivatives, their preparation and uses thereof |
WO2004058911A2 (de) | 2002-12-23 | 2004-07-15 | Covion Organic Semiconductors Gmbh | Organisches elektrolumineszenzelement |
JP2004288381A (ja) | 2003-03-19 | 2004-10-14 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子 |
WO2004093207A2 (de) | 2003-04-15 | 2004-10-28 | Covion Organic Semiconductors Gmbh | Mischungen von organischen zur emission befähigten halbleitern und matrixmaterialien, deren verwendung und elektronikbauteile enthaltend diese mischungen |
WO2004108857A1 (en) | 2003-06-02 | 2004-12-16 | Fuji Photo Film Co., Ltd. | Organic electroluminescent devices and metal complex compounds |
WO2005011013A1 (de) | 2003-07-21 | 2005-02-03 | Covion Organic Semiconductors Gmbh | Organisches elektrolumineszenzelement |
US20050069729A1 (en) | 2003-09-30 | 2005-03-31 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, illuminator, display and compound |
WO2005042550A1 (de) | 2003-10-30 | 2005-05-12 | Merck Patent Gmbh | Metallkomplexe mit bipodalen liganden |
WO2005042444A2 (ja) | 2003-11-04 | 2005-05-12 | Takasago Perfumery Co Ltd | 白金錯体及び発光素子 |
WO2005111172A2 (de) | 2004-05-11 | 2005-11-24 | Merck Patent Gmbh | Neue materialmischungen für die elektrolumineszenz |
JP2005347160A (ja) | 2004-06-04 | 2005-12-15 | Konica Minolta Holdings Inc | 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 |
EP1617710A1 (de) | 2003-04-23 | 2006-01-18 | Konica Minolta Holdings, Inc. | Material für ein organisches elektrolumineszenzgerät, organisches elektrolumineszenzgerät, beleuchtungsvorrichtung und anzeige |
WO2006005627A1 (en) | 2004-07-15 | 2006-01-19 | Merck Patent Gmbh | Oligomeric derivatives of spirobifluorene, their preparation and use |
WO2006117052A1 (de) | 2005-05-03 | 2006-11-09 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung und in deren herstellung verwendete boronsäure- und borinsäure-derivate |
EP1731584A1 (de) | 2004-03-31 | 2006-12-13 | Konica Minolta Holdings, Inc. | Organischer elektrolumineszenzvorrichtungsstoff, organische elektrolumineszenzvorrichtung, display und beleuchtungsvorrichtung |
WO2007063754A1 (ja) | 2005-12-01 | 2007-06-07 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子用化合物及び有機電界発光素子 |
WO2007137725A1 (de) | 2006-05-31 | 2007-12-06 | Merck Patent Gmbh | Neue materialien für organische elektrolumineszenzvorrichtungen |
WO2008056746A1 (fr) | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique |
WO2008086851A1 (de) | 2007-01-18 | 2008-07-24 | Merck Patent Gmbh | Carbazol-derivate für organische elektrolumineszenzvorrichtungen |
WO2009062578A1 (de) | 2007-11-12 | 2009-05-22 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtungen enthaltend azomethin-metall-komplexe |
US20090136779A1 (en) | 2007-11-26 | 2009-05-28 | Chien-Hong Cheng | Conjugated compounds containing hydroindoloacridine structural elements, and their use |
US20090134784A1 (en) | 2004-10-21 | 2009-05-28 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
EP2113548A1 (de) * | 2008-04-24 | 2009-11-04 | FUJIFILM Corporation | Organische Elektrolumineszenzvorrichtung |
WO2009148015A1 (ja) | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | ハロゲン化合物、多環系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 |
WO2010006680A1 (de) | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2010015306A1 (de) | 2008-08-08 | 2010-02-11 | Merck Patent Gmbh, | Organische elektrolumineszenzvorrichtung |
WO2010050778A1 (en) | 2008-10-31 | 2010-05-06 | Gracel Display Inc. | Novel compounds for organic electronic material and organic electronic device using the same |
WO2010054730A1 (de) | 2008-11-11 | 2010-05-20 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtungen |
WO2010054729A2 (de) | 2008-11-11 | 2010-05-20 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2010108579A1 (de) | 2009-03-23 | 2010-09-30 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
WO2010136109A1 (de) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2011000455A1 (de) | 2009-06-30 | 2011-01-06 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2011042107A2 (de) | 2009-10-08 | 2011-04-14 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2011088877A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060134461A1 (en) * | 2004-12-17 | 2006-06-22 | Shouquan Huo | Organometallic materials and electroluminescent devices |
JP2008037848A (ja) | 2006-08-10 | 2008-02-21 | Takasago Internatl Corp | 白金錯体及び発光素子 |
ATE512206T1 (de) * | 2007-03-28 | 2011-06-15 | Fujifilm Corp | Organische elektrolumineszenzvorrichtung |
US9312505B2 (en) * | 2012-09-25 | 2016-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
2012
- 2012-05-10 WO PCT/EP2012/002013 patent/WO2012163471A1/de active Application Filing
- 2012-05-10 CN CN201280027277.2A patent/CN103619860B/zh active Active
- 2012-05-10 KR KR1020147000235A patent/KR101972184B1/ko active IP Right Grant
- 2012-05-10 EP EP12726734.2A patent/EP2714704B1/de active Active
- 2012-05-10 US US14/122,844 patent/US10103340B2/en active Active
- 2012-05-10 JP JP2014513070A patent/JP6125492B2/ja active Active
Patent Citations (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
EP0652273A1 (de) | 1993-11-09 | 1995-05-10 | Shinko Electric Industries Co. Ltd. | Organisches Material für elektrolumineszente Vorrichtung und elektrolumineszente Vorrichtung |
EP0676461A2 (de) | 1994-04-07 | 1995-10-11 | Hoechst Aktiengesellschaft | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
WO1998027136A1 (de) | 1996-12-16 | 1998-06-25 | Aventis Research & Technologies Gmbh & Co Kg | ARYLSUBSTITUIERTE POLY(p-ARYLENVINYLENE), VERFAHREN ZUR HERSTELLUNG UND DEREN VERWENDUNG IN ELEKTROLUMINESZENZBAUELEMENTEN |
EP1205527A1 (de) | 2000-03-27 | 2002-05-15 | Idemitsu Kosan Co., Ltd. | Organische elektrolumineszierende vorrichtung |
WO2004013080A1 (en) | 2002-08-01 | 2004-02-12 | Covion Organic Semiconductors Gmbh | Spirobifluorene derivatives, their preparation and uses thereof |
WO2004058911A2 (de) | 2002-12-23 | 2004-07-15 | Covion Organic Semiconductors Gmbh | Organisches elektrolumineszenzelement |
JP2004288381A (ja) | 2003-03-19 | 2004-10-14 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子 |
WO2004093207A2 (de) | 2003-04-15 | 2004-10-28 | Covion Organic Semiconductors Gmbh | Mischungen von organischen zur emission befähigten halbleitern und matrixmaterialien, deren verwendung und elektronikbauteile enthaltend diese mischungen |
EP1617710A1 (de) | 2003-04-23 | 2006-01-18 | Konica Minolta Holdings, Inc. | Material für ein organisches elektrolumineszenzgerät, organisches elektrolumineszenzgerät, beleuchtungsvorrichtung und anzeige |
EP1617711A1 (de) | 2003-04-23 | 2006-01-18 | Konica Minolta Holdings, Inc. | Organisches elektrolumineszenzbauelement und anzeige |
WO2004108857A1 (en) | 2003-06-02 | 2004-12-16 | Fuji Photo Film Co., Ltd. | Organic electroluminescent devices and metal complex compounds |
WO2005011013A1 (de) | 2003-07-21 | 2005-02-03 | Covion Organic Semiconductors Gmbh | Organisches elektrolumineszenzelement |
WO2005039246A1 (ja) | 2003-09-30 | 2005-04-28 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、照明装置、表示装置 |
US20050069729A1 (en) | 2003-09-30 | 2005-03-31 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, illuminator, display and compound |
WO2005042550A1 (de) | 2003-10-30 | 2005-05-12 | Merck Patent Gmbh | Metallkomplexe mit bipodalen liganden |
WO2005042444A2 (ja) | 2003-11-04 | 2005-05-12 | Takasago Perfumery Co Ltd | 白金錯体及び発光素子 |
EP1683804A2 (de) * | 2003-11-04 | 2006-07-26 | Takasago International Corporation | Platinkomplex und lumineszentes element |
EP1731584A1 (de) | 2004-03-31 | 2006-12-13 | Konica Minolta Holdings, Inc. | Organischer elektrolumineszenzvorrichtungsstoff, organische elektrolumineszenzvorrichtung, display und beleuchtungsvorrichtung |
WO2005111172A2 (de) | 2004-05-11 | 2005-11-24 | Merck Patent Gmbh | Neue materialmischungen für die elektrolumineszenz |
JP2005347160A (ja) | 2004-06-04 | 2005-12-15 | Konica Minolta Holdings Inc | 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 |
WO2006005627A1 (en) | 2004-07-15 | 2006-01-19 | Merck Patent Gmbh | Oligomeric derivatives of spirobifluorene, their preparation and use |
US20090134784A1 (en) | 2004-10-21 | 2009-05-28 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
WO2006117052A1 (de) | 2005-05-03 | 2006-11-09 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung und in deren herstellung verwendete boronsäure- und borinsäure-derivate |
WO2007063754A1 (ja) | 2005-12-01 | 2007-06-07 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子用化合物及び有機電界発光素子 |
WO2007137725A1 (de) | 2006-05-31 | 2007-12-06 | Merck Patent Gmbh | Neue materialien für organische elektrolumineszenzvorrichtungen |
WO2008056746A1 (fr) | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique |
WO2008086851A1 (de) | 2007-01-18 | 2008-07-24 | Merck Patent Gmbh | Carbazol-derivate für organische elektrolumineszenzvorrichtungen |
WO2009062578A1 (de) | 2007-11-12 | 2009-05-22 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtungen enthaltend azomethin-metall-komplexe |
US20090136779A1 (en) | 2007-11-26 | 2009-05-28 | Chien-Hong Cheng | Conjugated compounds containing hydroindoloacridine structural elements, and their use |
EP2113548A1 (de) * | 2008-04-24 | 2009-11-04 | FUJIFILM Corporation | Organische Elektrolumineszenzvorrichtung |
WO2009148015A1 (ja) | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | ハロゲン化合物、多環系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 |
WO2010006680A1 (de) | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2010015306A1 (de) | 2008-08-08 | 2010-02-11 | Merck Patent Gmbh, | Organische elektrolumineszenzvorrichtung |
WO2010050778A1 (en) | 2008-10-31 | 2010-05-06 | Gracel Display Inc. | Novel compounds for organic electronic material and organic electronic device using the same |
WO2010054730A1 (de) | 2008-11-11 | 2010-05-20 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtungen |
WO2010054729A2 (de) | 2008-11-11 | 2010-05-20 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2010108579A1 (de) | 2009-03-23 | 2010-09-30 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
WO2010136109A1 (de) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2011000455A1 (de) | 2009-06-30 | 2011-01-06 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2011042107A2 (de) | 2009-10-08 | 2011-04-14 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2011088877A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
Non-Patent Citations (3)
Title |
---|
M. A. BALDO ET AL., APPL. PHYS. LETT., vol. 75, 1999, pages 4 - 6 |
M. S. ARNOLD ET AL., APPL. PHYS. LETT., vol. 92, 2008, pages 053301 |
MASATO KURATSU ET AL: "Magnetic Interaction of Tri- and Di-oxytriphenylamine Radical Cation FeCl 4 Salts", INORGANIC CHEMISTRY, vol. 46, no. 24, 1 November 2007 (2007-11-01), pages 10153 - 10157, XP055033662, ISSN: 0020-1669, DOI: 10.1021/ic7012649 * |
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US11472827B2 (en) | 2015-06-03 | 2022-10-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
US9617291B2 (en) | 2015-06-03 | 2017-04-11 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
US9879039B2 (en) | 2015-06-03 | 2018-01-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
US10836785B2 (en) | 2015-06-03 | 2020-11-17 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues |
US11930662B2 (en) | 2015-06-04 | 2024-03-12 | Arizona Board Of Regents On Behalf Of Arizona State University | Transparent electroluminescent devices with controlled one-side emissive displays |
WO2016198144A1 (en) | 2015-06-10 | 2016-12-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP3124488A1 (de) | 2015-07-29 | 2017-02-01 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4301110A2 (de) | 2015-07-30 | 2024-01-03 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
WO2017016630A1 (en) | 2015-07-30 | 2017-02-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US10930865B2 (en) | 2015-08-04 | 2021-02-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes, devices, and uses thereof |
EP3159350A1 (de) | 2015-09-03 | 2017-04-26 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
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WO2017071791A1 (en) | 2015-10-27 | 2017-05-04 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP3205658A1 (de) | 2016-02-09 | 2017-08-16 | Universal Display Corporation | Organische elektrolumineszenzmaterialien und vorrichtungen |
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US11335865B2 (en) | 2016-04-15 | 2022-05-17 | Arizona Board Of Regents On Behalf Of Arizona State University | OLED with multi-emissive material layer |
EP3261146A2 (de) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
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EP3261147A1 (de) | 2016-06-20 | 2017-12-27 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3270435A2 (de) | 2016-06-20 | 2018-01-17 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
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US10566554B2 (en) | 2016-08-22 | 2020-02-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes and octahedral iridium complexes employing azepine functional groups and their analogues |
US10177323B2 (en) | 2016-08-22 | 2019-01-08 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum (II) and palladium (II) complexes and octahedral iridium complexes employing azepine functional groups and their analogues |
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US10822363B2 (en) | 2016-10-12 | 2020-11-03 | Arizona Board Of Regents On Behalf Of Arizona State University | Narrow band red phosphorescent tetradentate platinum (II) complexes |
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US11708385B2 (en) | 2017-01-27 | 2023-07-25 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emitters employing pyrido-pyrrolo-acridine and analogues |
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US11063228B2 (en) | 2017-05-19 | 2021-07-13 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emitters employing benzo-imidazo-phenanthridine and analogues |
US11101435B2 (en) | 2017-05-19 | 2021-08-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complexes based on biscarbazole and analogues |
US11974495B2 (en) | 2017-05-19 | 2024-04-30 | Arizona Board Of Regents On Behalf Of Arizona State University | Tetradentate platinum and palladium complexes based on biscarbazole and analogues |
US10516117B2 (en) | 2017-05-19 | 2019-12-24 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emttters employing benzo-imidazo-phenanthridine and analogues |
US12010908B2 (en) | 2017-05-19 | 2024-06-11 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal-assisted delayed fluorescent emitters employing benzo-imidazo-phenanthridine and analogues |
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EP4185086A1 (de) | 2017-07-26 | 2023-05-24 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3444258A2 (de) | 2017-08-10 | 2019-02-20 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
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US11594688B2 (en) | 2017-10-17 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Display and lighting devices comprising phosphorescent excimers with preferred molecular orientation as monochromatic emitters |
US11647643B2 (en) | 2017-10-17 | 2023-05-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Hole-blocking materials for organic light emitting diodes |
US10886476B2 (en) | 2017-10-24 | 2021-01-05 | Samsung Display Co., Ltd. | Polycyclic compound and organic electroluminescence device including the same |
EP3489243A1 (de) | 2017-11-28 | 2019-05-29 | University of Southern California | Carbenverbindungen und organische elektrolumineszente vorrichtungen |
EP3878855A1 (de) | 2017-11-28 | 2021-09-15 | University of Southern California | Carbenverbindungen und organische elektrolumineszente vorrichtungen |
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EP3492528A1 (de) | 2017-11-30 | 2019-06-05 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
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US12037348B2 (en) | 2018-03-09 | 2024-07-16 | Arizona Board Of Regents On Behalf Of Arizona State University | Blue and narrow band green and red emitting metal complexes |
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WO2020053150A1 (en) | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2020053315A1 (de) | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Elektrolumineszierende vorrichtungen |
WO2020053314A1 (de) | 2018-09-12 | 2020-03-19 | Merck Patent Gmbh | Elektrolumineszierende vorrichtungen |
DE202019005924U1 (de) | 2018-09-12 | 2023-05-10 | MERCK Patent Gesellschaft mit beschränkter Haftung | Elektrolumineszierende Vorrichtungen |
DE202019005923U1 (de) | 2018-09-12 | 2023-06-27 | MERCK Patent Gesellschaft mit beschränkter Haftung | Elektrolumineszierende Vorrichtungen |
US11878988B2 (en) | 2019-01-24 | 2024-01-23 | Arizona Board Of Regents On Behalf Of Arizona State University | Blue phosphorescent emitters employing functionalized imidazophenthridine and analogues |
US11594691B2 (en) | 2019-01-25 | 2023-02-28 | Arizona Board Of Regents On Behalf Of Arizona State University | Light outcoupling efficiency of phosphorescent OLEDs by mixing horizontally aligned fluorescent emitters |
EP3690973A1 (de) | 2019-01-30 | 2020-08-05 | University Of Southern California | Organische elektrolumineszente materialien und vorrichtungen |
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WO2020178230A1 (en) | 2019-03-04 | 2020-09-10 | Merck Patent Gmbh | Ligands for nano-sized materials |
EP3715353A1 (de) | 2019-03-26 | 2020-09-30 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4134371A2 (de) | 2019-03-26 | 2023-02-15 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2020208051A1 (en) | 2019-04-11 | 2020-10-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP3750897A1 (de) | 2019-06-10 | 2020-12-16 | Universal Display Corporation | Organische elektrolumineszente materialien und geräte |
EP3771717A1 (de) | 2019-07-30 | 2021-02-03 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
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EP3778614A1 (de) | 2019-08-16 | 2021-02-17 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
US11785838B2 (en) | 2019-10-02 | 2023-10-10 | Arizona Board Of Regents On Behalf Of Arizona State University | Green and red organic light-emitting diodes employing excimer emitters |
WO2021089450A1 (en) | 2019-11-04 | 2021-05-14 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP3816175A1 (de) | 2019-11-04 | 2021-05-05 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2021094269A1 (en) | 2019-11-12 | 2021-05-20 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2021110741A1 (en) | 2019-12-04 | 2021-06-10 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP4151644A1 (de) | 2020-01-06 | 2023-03-22 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3845545A1 (de) | 2020-01-06 | 2021-07-07 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP4294157A2 (de) | 2020-01-28 | 2023-12-20 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
EP3858945A1 (de) | 2020-01-28 | 2021-08-04 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2021151922A1 (de) | 2020-01-29 | 2021-08-05 | Merck Patent Gmbh | Benzimidazol-derivate |
WO2021191058A1 (en) | 2020-03-23 | 2021-09-30 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US11945985B2 (en) | 2020-05-19 | 2024-04-02 | Arizona Board Of Regents On Behalf Of Arizona State University | Metal assisted delayed fluorescent emitters for organic light-emitting diodes |
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EP4075531A1 (de) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonische oleds und vertikale dipolstrahler |
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EP4362631A2 (de) | 2022-10-27 | 2024-05-01 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
WO2024105066A1 (en) | 2022-11-17 | 2024-05-23 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP4386065A1 (de) | 2022-12-14 | 2024-06-19 | Universal Display Corporation | Organische elektrolumineszente materialien und vorrichtungen |
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KR101972184B1 (ko) | 2019-04-24 |
EP2714704A1 (de) | 2014-04-09 |
US20140091265A1 (en) | 2014-04-03 |
US10103340B2 (en) | 2018-10-16 |
JP2014520096A (ja) | 2014-08-21 |
CN103619860A (zh) | 2014-03-05 |
EP2714704B1 (de) | 2015-04-29 |
JP6125492B2 (ja) | 2017-05-10 |
CN103619860B (zh) | 2016-08-17 |
KR20140041683A (ko) | 2014-04-04 |
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