WO2005040302A1 - Neue materialien für die elektrolumineszenz und deren verwendung - Google Patents
Neue materialien für die elektrolumineszenz und deren verwendung Download PDFInfo
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- WO2005040302A1 WO2005040302A1 PCT/EP2004/011888 EP2004011888W WO2005040302A1 WO 2005040302 A1 WO2005040302 A1 WO 2005040302A1 EP 2004011888 W EP2004011888 W EP 2004011888W WO 2005040302 A1 WO2005040302 A1 WO 2005040302A1
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- 239000000463 material Substances 0.000 title abstract description 10
- 238000005401 electroluminescence Methods 0.000 title description 3
- 239000004065 semiconductor Substances 0.000 claims abstract description 34
- 229920000642 polymer Polymers 0.000 claims description 126
- 239000000203 mixture Substances 0.000 claims description 86
- 150000001875 compounds Chemical class 0.000 claims description 39
- -1 silylthio group Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052711 selenium Inorganic materials 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000879 imine group Chemical group 0.000 claims description 8
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 8
- 239000004793 Polystyrene Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 claims description 6
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 4
- 229920001643 poly(ether ketone) Polymers 0.000 claims description 4
- FXCSCTVYEKPPDO-UHFFFAOYSA-N (2-ethenylphenyl)-phenylmethanone Chemical class C=CC1=CC=CC=C1C(=O)C1=CC=CC=C1 FXCSCTVYEKPPDO-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 229910052714 tellurium Inorganic materials 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- 229920003235 aromatic polyamide Polymers 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002527 isonitriles Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
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- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 229920006393 polyether sulfone Polymers 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 claims description 2
- 229920001470 polyketone Polymers 0.000 claims description 2
- 229920001184 polypeptide Polymers 0.000 claims description 2
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- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 229920001567 vinyl ester resin Polymers 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
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- 238000000034 method Methods 0.000 description 11
- 0 Cc(cc1)ccc1C(c1ccc(C)cc1)=N* Chemical compound Cc(cc1)ccc1C(c1ccc(C)cc1)=N* 0.000 description 10
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- 101000915578 Homo sapiens Zinc finger HIT domain-containing protein 3 Proteins 0.000 description 8
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- URGNHDJCYWEAKG-UHFFFAOYSA-N 1-bromo-4-[(4-bromophenyl)-phenylphosphoryl]benzene Chemical compound C1=CC(Br)=CC=C1P(=O)(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 URGNHDJCYWEAKG-UHFFFAOYSA-N 0.000 description 2
- PZQYZICYHUJKSJ-UHFFFAOYSA-N 2,7-dibromo-10-(2-ethylhexyl)-10-hydroxy-1,2-dihydrophenanthren-9-one Chemical compound C1C(Br)C=CC2=C1C(CC(CC)CCCC)(O)C(=O)C1=CC(Br)=CC=C12 PZQYZICYHUJKSJ-UHFFFAOYSA-N 0.000 description 2
- IDZUJCHNUVDSFM-UHFFFAOYSA-N 2,7-dibromo-10-(2-ethylhexyl)-10-methoxy-1,2-dihydrophenanthren-9-one Chemical compound C1C(Br)C=CC2=C1C(CC(CC)CCCC)(OC)C(=O)C1=CC(Br)=CC=C12 IDZUJCHNUVDSFM-UHFFFAOYSA-N 0.000 description 2
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XQTRLZHQNYWEQN-UHFFFAOYSA-N bis(4-bromophenyl)-phenylphosphane Chemical compound C1=CC(Br)=CC=C1P(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 XQTRLZHQNYWEQN-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
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- 229910052703 rhodium Inorganic materials 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
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- 125000005259 triarylamine group Chemical group 0.000 description 2
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
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- OELHQHILWOIUSL-UHFFFAOYSA-N 3-bromooctane Chemical compound CCCCCC(Br)CC OELHQHILWOIUSL-UHFFFAOYSA-N 0.000 description 1
- DSNQPNGWFBNTQE-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3,5,6-tetraphenylaniline Chemical group C1=CC(N)=CC=C1C(C(=C(C=1C=CC=CC=1)C(N)=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C1=CC=CC=C1 DSNQPNGWFBNTQE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- RUJGPRQBHCCTEC-UTCJRWHESA-N C/C=C\C(c1ccccc11)=C(C)C1(c1c2)c(cc(cc3)[NH+](C4=CC=[I]C=C4)[O-])c3-c1ccc2[NH+](c(cc1)ccc1I)[O-] Chemical compound C/C=C\C(c1ccccc11)=C(C)C1(c1c2)c(cc(cc3)[NH+](C4=CC=[I]C=C4)[O-])c3-c1ccc2[NH+](c(cc1)ccc1I)[O-] RUJGPRQBHCCTEC-UTCJRWHESA-N 0.000 description 1
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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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
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- 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 describes new materials and material mixtures for use in organic electronic components and their use in displays based thereon.
- PLEDs LEDs
- Phosphine oxides, sulfones and sulfoxides achieved excellent results in terms of both the efficiency and the life of the devices.
- the triplet emitter can also be covalently bound to the polymer. Both methods have the advantage that the compounds can be processed from solution and that no expensive and complex vapor deposition process is required as for devices based on low molecular weight compounds.
- WO 04/070772 describes blends and copolymers of triplet emitters with certain carbazole-containing conjugated polymers, which result in efficient emission and reduced operating voltage. A further improvement was achieved by introducing certain bridged carbazole units, as described in the unpublished application DE 10328627.6.
- WO 03/099901 there is a coincidental disclosure of a copolymer according to the invention from a polymer backbone which contains ester groups (or also carbonyl, sulfone, sulfoxide or phosphine oxide groups) and polymerized iridium and platinum complexes.
- ester groups or also carbonyl, sulfone, sulfoxide or phosphine oxide groups
- polymerized iridium and platinum complexes are therefore excluded from the invention.
- the invention relates to organic semiconductors containing (A) at least one polymer,
- M represents a group represented by formula (b), formula (c) or formula (d).
- R 17 and R 18 each independently represent N, B, P, C (R 17 ) or Si (R 18 ); in formula (c) the radicals R 17 and R 18 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, a Alkylamino group, an aryl group, an aryloxy group, an arylthio group, an arylamino group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkylamino group, an acyl group, an acyloxy group, an amide group, an imine group, a substituted silyloxy group, a substituted siyogyl group, a substituted siyogyl group, a substituted siyogyl group, a substituted siyogyl group, a substituted siyi group, a a substituted one
- Acyl group an acyloxy group, an amide group, an imine group, a substituted siiyi group, a substituted silyloxy group, a substituted silylthio group, a substituted silylamino group, a monovalent heterocyclic group, an arylalkenyl group, an arylethinyl group or a cyano group);
- Preferred structural units L X, as described above, are therefore selected from the formulas (1) to (5),
- Formula (1) Formula (2) Formula (3) Formula (4) Formula (5) where the symbols used have the following meaning: X is the same or different at each occurrence O, S, Se or NR 4 , with the proviso that X for formulas (4) and (5) must not be S or Se; Y is the same or different at each occurrence P, As, Sb or Bi; Z is the same or different at each occurrence S, Se or Te; R 1 to R 6 have the same meaning as described above.
- the organic semiconductors according to the invention are preferably in the form of amorphous compounds or amorphous mixtures.
- An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as a system which does not necessarily contain only aromatic or heteroaromatic groups, but also in which several aromatic or heteroaromatic groups by a short, non-aromatic unit ( ⁇ 10% of that of H different atoms, preferably ⁇ 5% of the atoms different from H), such as.
- B. an sp 3 hybridized C, N or O atom may be interrupted.
- systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, etc. should also be understood as aromatic ring systems in the sense of this application.
- Organic semiconductors for the purposes of this application are low-molecular, oligomeric, dendritic or polymeric, organic or organometallic compounds which have semiconducting properties as a solid or as a layer, ie. H. where the energy gap between the conduction and valence band is between 1.0 and 3.5 eV. Either a pure component or a
- electronically inert connections such as. As polystyrene, can be used together with semiconducting compounds.
- the organic semiconductor is in the form of a mixture. In a further preferred embodiment of the invention, the organic semiconductor is present as a copolymer.
- a triplet emitter in the sense of the invention is to be understood as a compound which emits light from the triplet state, that is to say shows phosphorescence instead of fluorescence in electroluminescence, preferably an organometallic triplet emitter.
- this compound can be low molecular weight, oligomeric, dendritic or polymeric.
- all emitting compounds which contain the elements Ru, Os, Rh, Ir, Pd, Pt are referred to as triplet emitters.
- One embodiment of the invention is mixtures containing BLEND1
- TRIP1 triplet emitters
- the triplet emitter (TRIP1) is non-covalently mixed with the polymer POLY1.
- Position take place ie these units can be installed in one or more positions at R 1 to R 3 or optionally via R 4 , R 5 and / or R 6 in formulas (1) to (5). Depending on the linkage, these structural units are then built into the main or side chain of the polymer.
- the triplet emitter TRIP2 can be installed in the main and / or in the side chain of the polymer POLY2.
- Another aspect of this invention are mixtures containing BLEND3
- (B) 1-99% by weight of at least one compound VERB1 which. contains at least one structural unit L X, or at least one structural unit of the formula (1) to (5) and is able to form glass-like layers at room temperature, preferably with a glass transition temperature greater than 70 ° C .; and also
- TRIP1 triplet emitters
- Another aspect of this invention are mixtures containing BLEND4
- Another object of the invention are polymers containing POLY4
- the proportion of triplet emitters in BLEND1 to BLEND4 and POLY4 can also be significantly lower than stated above. A smaller proportion of the triplet emitters may be preferred in particular for generating white emission, as described in the unpublished application DE 10343606.5.
- the polymers POLY1 to POLY4 can be conjugated, partially conjugated, cross-conjugated or non-conjugated.
- Conjugated polymers in the sense of this invention are polymers which in the
- Main chain mainly contain sp 2 -hybridized (or also sp-hybridized) carbon atoms, which can also be replaced by corresponding heteroatoms and whose units are in conjugation with one another. In the simplest case, this means alternating double and single bonds in the main chain. Mainly means that naturally occurring (without further action) defects that lead to interruptions in conjugation do not invalidate the term "conjugated polymer". Furthermore, in this application text is also referred to as conjugated if there are arylamine units, arylphosphine units and / or certain heterocycles (ie conjugation via N, O, S or P atoms) and / or organometallic complexes, for example, in the main chain
- partially conjugated polymers are polymers which either contain longer conjugated sections in the main chain, which are interrupted by non-conjugated sections, or which contain longer conjugated sections in the side chains of a polymer which is non-conjugated in the main chain.
- Cross-conjugated polymers in the sense of this invention are polymers in which two conjugated sections do not conjugate with one another, but each of these sections is conjugated with a third unit. This is the case, for example, if two conjugated sections directly over a keto group, one. Sulfoxide group, a sulfone group or a phosphine oxide group are linked, but also, for example, when two conjugated sections are linked geminally via a substituted or unsubstituted alkene group, or when two conjugated sections are linked via, for example, a meta-phenylene group.
- polymers POLYI to POLY4 can contain various other structural elements. These can be, for example, structural units that can form the polymer backbone or structural units that influence the charge injection or charge transport properties. Such units are described in detail, for example, in WO 03/020790 and in the unpublished application DE 10337346.2. The statements made there are part of the present application via quotation.
- a suitable class of compound for cross-conjugated polymers POLY1 or POLY4 are aromatic polyketones and aromatic polysulfones, which can each be substituted for better solubility.
- An overview of these classes of compounds is given by PA Staniland in "Comprehensive Polymer Science", Ed. G. Allen, Volume 5, Chapter 29, 483-497 and F. Parodi, ibid., Chapter 33, 561-DD? ⁇ . I ucno ⁇ r ⁇ .ur ⁇ i ⁇ i and ICIIIS I i; ruiypi ⁇ o ⁇ i ⁇ iu ⁇ IM ri ⁇ yc.
- any class of compound can in principle be considered, provided that the polymers, when processed as a blend, have sufficient solubility0 in a solvent or a solvent mixture in which the other blend components are soluble, so that all components can be processed together from solution.
- polycarboxylic acid derivatives in the broadest sense, such as main chain polyester, side chain polyester , Poly (gly
- polymers which have bonded directly to the carbonyl group at least one aromatic group, particularly preferably two aromatic groups.
- main chains - 5 polyester would be z.
- side chain polyesters would e.g. B. poly (acrylates), in particular poly (phenyl acrylates), poly (cyanoacrylates), poly (vinyl esters) or poly (vinyl acetates).
- substituted or unsubstituted poly preferably aromatic polyvinyl ketones, or also substituted or unsubstituted poly (vinyl benzophenones) or other polystyrene analog ketones, like
- Polystyrene such as poly-nitriles or poly-isonitriles, are also suitable.
- the polymers POLY1, POLY2 and POLY3 can be homopolymers, i.e. H. they then contain only a single monomer structure, but are generally copolymers.
- the polymer POLY4 is always a copolymer.
- the copolymers can have statistical, alternating or block-like structures or alternately have several of these structures.
- the polymers can also be linear or dendritic. By using several different structural elements, properties such. B. solubility, solid phase morphology, etc., can be set.
- the polymers POLY1 to POLY4 are produced by polymerizing one or more monomers. Especially for the synthesis of conjugated or cross-conjugated polymers, some types have proven themselves that lead to CC linkages (SUZUKI coupling, YAMAMOTO coupling, STILLE coupling) or to CN linkages (HARTWIG-BUCHWALD coupling). How the polymerization can be carried out using these methods and how the polymers can be separated from the reaction medium and purified is described, for example, in WO 03/048225 and WO 04/022626. These methods can also be used to carry out the synthesis of partially conjugated or non-conjugated polymers by using appropriate monomers which are not conjugated throughout.
- polycondensation which, for. B. lead to ester or amide linkages, or cationic, anionic or radical polymerizations, for example the reaction of alkenes takes place and leads to polyethylene derivatives in the broadest sense, which contain the chromophores bound in the side chains.
- X represents O, S or NR 4 ;
- Y stands for P or As
- Z stands for S or Se
- R 1 to R 6 are as defined above, wherein at each structural unit according to formulas (1) to (5) at least one of the substituents R 1 to R 3 is an aromatic or heteroaromatic ring system with 1 to 40 C atoms, which is substituted with one or several substituents R 4 may be substituted or unsubstituted.
- X represents O or NR 4 ; X very particularly preferably represents O;
- R 1 to R 6 are as defined above, where on each structural unit according to formulas (1) to (5) all substituents R 1 to R 3 are aromatic or. represent heteroaromatic ring system with 1 to 40 C atoms, which can be substituted with one or more substituents R 4 or unsubstituted.
- the substituents R 1 to R 3 very particularly preferably contain aromatic or heteroaromatic ring systems in which at least one is biphenyl-like
- Structure is bound directly to the units according to formulas (1) to (5), structures such as fluorenes or spirobifluorenes also being counted as such structures.
- Preferred structural units according to formulas (1) to (5) have been found to be those whose radicals R 1 to R 3 are not planar. This is particularly the case if at least one of the substituents R 1 to R 3 contains an sp 3 -hybridized carbon atom (or correspondingly also silicon, germanium, nitrogen, etc.), which is thereby approximately tetrahedral (or in the case of nitrogen pyramidal) Has geometry. Preferred structural units are therefore units of the formula (1) to formula (5) in which at least one of the substituents R 1 to R 3 contains at least one sp 3 -hybridized carbon atom.
- this sp 3 -hybridized carbon atom is a secondary, tertiary or is a quaternary carbon atom, particularly preferred is a tertiary or quaternary carbon atom, very particularly preferred is a quaternary carbon atom.
- a secondary, tertiary or quaternary carbon atom is understood to mean a carbon atom with two, three or four substituents other than hydrogen.
- Structural units of the formula (1) to formula (5) are particularly preferred which contain in at least one of the radicals R 1 to R 3 a 9,9'-spirobifluorene derivative, a 9,9-disubstituted fluorene derivative, a 6,6- and / or Contain 12,12-di- or tetrasubstituted indenofluorene derivative, a triptycene derivative (preferably linked via position 9 and / or 10) or a tetraarylmethane derivative.
- Structural units of the formulas (1) to (5) which contain a 9,9'-spirobifluorene derivative in at least one of the radicals R 1 to R 3 are very particularly preferred.
- Examples of particularly preferred repeating units MONO1 or compounds VERB1 which contain structural units according to the formulas (1) to (5) are substituted or unsubstituted structures according to the formulas (6) to (148) shown, the dashed single bonds being a possible link in the Mean polymer (MONO1) or linkages for molecular extension (VERB1); Ph stands for a substituted or unsubstituted phenyl group and alkyl for a straight-chain, branched or cyclic alkyl chain, which can be substituted or unsubstituted and in which one or more H atoms can be replaced by fluorine.
- MONO1 Mean polymer
- VERB1 linkages for molecular extension
- Substituents R 4 can be present, or they can also be bound to different positions.
- the repeating units MONO1 are covalent components of POLY1 and POLY4. It has been shown that a share in the range of 5 - 100 mol% of this
- Repeat units (based on all repeat units in the polymer) achieved good results here.
- a proportion of 5-100 mol% repeating units MONO1 is preferred for POLY1.
- a proportion of 10-80 mol% of repeating units MONO1 is particularly preferred, a proportion of 10-50 mol% of repeating units MONO1 is very particularly preferred.
- Compounds VERB1 are part of the mixture of BLEND2 and BLEND3. It has been shown that a proportion in the range of 5-99% by weight of these compounds in the mixture achieves good results here. A proportion of 5-99% by weight of compounds VERB1 is therefore preferred for BLEND2 and BLEND3. A proportion of 10-80% by weight of VERB1 is particularly preferred, a proportion of 10-50% by weight of VERB1 is very particularly preferred.
- Results are achieved regardless of whether these units are covalently attached to the polymer or mixed.
- mixture BLEND7 which is formed by mixing compounds VERB1 and / or triplet emitters TRIP1 in POLY4.
- the triplet emitters TRIP1 and TRIP3 can be low molecular weight, oligomeric, dendritic or polymeric compounds. Since some of these are processed as a component of the mixture (BLEND1, BLEND3 or BLEND4), they must be sufficiently soluble in suitable solvents (e.g. toluene, xylene, anisole, THF, methylanisole, methylnaphthalene or mixtures of these solvents) in order to be processed is possible from solution. As a low molecular weight, oligomeric, dendritic or polymeric compounds. Since some of these are processed as a component of the mixture (BLEND1, BLEND3 or BLEND4), they must be sufficiently soluble in suitable solvents (e.g. toluene, xylene, anisole, THF, methylanisole, methylnaphthalene or mixtures of these solvents) in order to be processed is possible from solution. As a low molecular weight
- Structural units come into question here different complexes, which for example . are described in the application documents WO 02/068435, WO 02/081488, EP 1239526 and WO 04/026886.
- the halogenated complexes described in WO 02/068435 are also suitable as starting compounds for TRIPS, since the halogen functionality is easy
- Dendrimer structures for TRIPl or TRIP3 complexes are suitable, as described for example in WO 99/21935, WO 01/059030 and WO 02/066552.
- the triplet emitter TRIP2 is covalently built into the polymer chain of POLY2 (BLEND2).
- BLEND2 polymer chain of POLY2
- functional polymerizable groups must be present on TRIP2. Examples of corresponding brominated complexes which can be used as monomers in polymerization reactions, for example according to Suzuki or according to Yamamoto, are described in WO 02/068435 and in the unpublished application
- the blend BLEND1 according to the invention is obtained by the polymer
- a triplet emitter TRIP1 can be added to POLY1.
- the blend BLEND2 according to the invention is obtained by the polymer
- the blend BLEND3 according to the invention is obtained by the polymer
- the blend BLEND4 according to the invention is obtained by the polymer
- POLY3 units TRIP3 can be added. It can also be preferred to mix further conjugated, partially conjugated, cross-conjugated or non-conjugated polymers, oligomers, dendrimers or other low molecular weight compounds into BLEND1 to BLEND7.
- additional components can prove useful for some applications: For example, the addition of an electronically active substance can be used to regulate the hole or electron injection, the hole or electron transport or the charge balance in the corresponding blend.
- the additional component can also facilitate singlet-triplet transfer.
- the addition of electronically inert compounds can also be helpful, for example to determine the viscosity of a solution or the morphology of the formed
- BLEND1 to BLEND7 are represented as follows:
- the individual components of the blend are combined in a suitable mixing ratio and dissolved in a suitable solvent.
- suitable solvents are, for example, toluene, anisole, xylenes, methylanisole, methylnaphthalene, chlorobenzene, cyclic ethers (e.g. dioxane, THF, methyldioxane), amides (e.g. NMP, DMF) or mixtures of these solvents.
- the components of the blend can also be dissolved individually. The solution to the blend is obtained in this
- the organic semiconductors according to the invention that is to say the mixtures BLEND1 to BLEND7 and polymers POLY4 according to the invention, have the following surprising advantages over the prior art mentioned above: •
- the solubility in organic solvents is generally better than the solubility of the polymers and mixtures according to the prior art.
- the better solubility offers an advantage, for example, over bridged carbazole units, which are cited as the closest prior art, since there the maximum carbazole content is often determined by the poor solubility, but in some cases a higher carbazole content for the further improvement of the device properties would be desirable.
- mixtures and polymers according to the invention have a higher oxygen stability than mixtures and polymers according to the prior art. This simplifies the production of these compounds and mixtures and also their processing, which represents a considerable practical advantage.
- BLEND7 or the polymers POLY4 can be used in PLEDs, in particular as electroluminescent materials (emitting materials).
- a general procedure is generally used for the construction of PLEDs, which must be adapted accordingly for the individual case. Such a method has been described in detail, for example, in WO 04/037887.
- the invention therefore also relates to the use of an organic semiconductor according to the invention, that is to say a mixture BLEND1 to BLEND7 according to the invention or a polymer POLY4 according to the invention, in a PLED as electroluminescent material.
- the invention thus also relates to a PLED with one or more layers, at least one of these layers having one or more organic semiconductors according to the invention, that is to say one or more mixtures BLEND1 to BLEND7 according to the invention or polymers POLY4 according to the invention.
- organic semiconductors according to the invention ie mixtures BLEND1 to BLEND7 or polymers POLY4 according to the invention, in relation to PLEDs and the corresponding displays.
- polymers or blends according to the invention for other uses in other electronic devices (devices), for. B. for organic solar cells (O-SCs), non-linear optics or organic laser diodes (O-lasers), to name just a few applications.
- O-SCs organic solar cells
- O-lasers organic laser diodes
- 4,4'-D-bromobenzophenone was obtained from Fluka in a purity of 98% and purified by further recrystallization from ethanol to a purity of 99.7% (according to HPLC).
- Example 6 blend components V1 and V2 (VERB1 according to formula (1))
- Example 7 Structural units TRIP1 for use in blends
- the compounds TRIP1 used here as examples are derivatives of tris (phenylpyridyl) iridium (III). The synthesis of these compounds has already been described in WO 02/081488 and WO 04/026886. For an overview, the iridium complexes used here are shown again below:
- Example 8 Other blend components
- Example 12 Non-conjugated polymers (POLY1) P6 and P7
- Polystyrene P6 with melt index 7.5 was obtained commercially from ⁇ ldrich.
- Poly (vinylbenzophenone) P7 was synthesized according to Helv. Chim. Acta 1999, 82, 338-346.
- Example 13 Preparation of the blends The mixtures were prepared by dissolving the blend components in the desired ratio and in the desired concentration in Toiuol. The dissolving process was carried out in an inert atmosphere at 60 ° C. The solution was processed directly without isolating the mixture (further precipitation of the solids).
- Example 14 Production of polymeric light-emitting diodes (PLEDs) How PLEDs can be represented is described in detail, for example, in WO 04/037887 and the literature cited therein. It has been shown that the polymers and blends according to the invention form more homogeneous films than the polymers and blends according to the prior art. Without wishing to be bound by any particular theory, we suspect that this is due to the better solubility of these compounds.
- Example 15 Overview of the Polymers Synthesized and Used Table 1 gives an overview of the composition of some of the polymers synthesized and used in the devices.
- Example 16 Device Examples Table 2 gives an overview of various blends made of polymers and triplet emitters, possibly with other components. Table 2: Some device results with blends according to the invention a The proportion of the polymer or the other blend components relates to the total composition of all components except the triplet emitter. The proportion of the triplet emitter is based on the matrix, ie the polymer or the mixture of the polymer with the other constituents. 0 CIE coordinates: Chromaticity coordinates of the Commission Internationale de TEclairage from 1931. d The specified lifespan relates to the so-called LT50 value, ie the time that passes until the corresponding PLED has only 50% of the initial brightness; the values were determined with an initial sensitivity of 100 cd / m 2 .
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Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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US10/576,920 US7659540B2 (en) | 2003-10-22 | 2004-10-21 | Materials for electroluminescence and the utilization thereof |
EP04790695.3A EP1675930B1 (de) | 2003-10-22 | 2004-10-21 | Neue materialien für die elektrolumineszenz und deren verwendung |
JP2006536042A JP2007517079A (ja) | 2003-10-22 | 2004-10-21 | エレクトロルミネセンスのための新規材料、およびそれらの使用 |
KR1020067007587A KR101215160B1 (ko) | 2003-10-22 | 2006-04-20 | 전기발광을 위한 새로운 물질 및 그 용도 |
US12/639,591 US8173276B2 (en) | 2003-10-22 | 2009-12-16 | Materials for electroluminescence and the utilization thereof |
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DE10349033A DE10349033A1 (de) | 2003-10-22 | 2003-10-22 | Neue Materialien für die Elektrolumineszenz und deren Verwendung |
DE10349033.7 | 2003-10-22 | ||
DE102004003008.1 | 2004-01-20 | ||
DE102004003008A DE102004003008A1 (de) | 2004-01-20 | 2004-01-20 | Neue Materialien für die Elektrolumineszenz und deren Verwendung |
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US10/576,920 A-371-Of-International US7659540B2 (en) | 2003-10-22 | 2004-10-21 | Materials for electroluminescence and the utilization thereof |
US12/639,591 Division US8173276B2 (en) | 2003-10-22 | 2009-12-16 | Materials for electroluminescence and the utilization thereof |
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EP (2) | EP1675930B1 (de) |
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Cited By (256)
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WO2007022845A1 (de) | 2005-08-26 | 2007-03-01 | Merck Patent Gmbh | Neue materialien für organische elektrolumineszenzvorrichtungen |
JP2007087786A (ja) * | 2005-09-22 | 2007-04-05 | Toppan Printing Co Ltd | 有機エレクトロルミネッセンスインキ及びこれを用いた有機エレクトロルミネッセンス素子の製造方法 |
WO2007053357A2 (en) * | 2005-10-28 | 2007-05-10 | General Electric Company | Polymers, polymer compositions and method of preparation |
WO2007068325A1 (de) | 2005-12-17 | 2007-06-21 | Merck Patent Gmbh | Konjugierte polymere enthaltend triarylamin-arylvinylen-einheiten, deren darstellung und verwendung |
WO2007081058A1 (ja) * | 2006-01-16 | 2007-07-19 | Sumitomo Chemical Company, Limited | 高分子化合物およびそれを用いた高分子発光素子 |
JP2007224282A (ja) * | 2006-01-16 | 2007-09-06 | Sumitomo Chemical Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
EP1961780A1 (de) * | 2005-12-02 | 2008-08-27 | Sumitomo Chemical Company, Limited | Polymerverbvindung und lichtemittierende polymervorrichtung damit |
WO2008111658A1 (ja) | 2007-03-09 | 2008-09-18 | Sumitomo Chemical Company, Limited | 高分子化合物およびそれを含む組成物 |
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DE102008033943A1 (de) | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008045662A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Optoelektronische Vorrichtung |
DE102008044868A1 (de) | 2008-08-29 | 2010-03-04 | Merck Patent Gmbh | Elektrolumineszierende Polymere, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
DE102008045663A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Fluorverbrückte Assoziate für optoelektronische Anwendungen |
DE102008045664A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Optoelektronische Vorrichtung |
DE102008050841A1 (de) | 2008-10-08 | 2010-04-15 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008054141A1 (de) | 2008-10-31 | 2010-05-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008056688A1 (de) | 2008-11-11 | 2010-05-12 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008057051A1 (de) | 2008-11-13 | 2010-05-20 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008057050A1 (de) | 2008-11-13 | 2010-05-20 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009005288A1 (de) | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009005289A1 (de) | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2010083869A2 (de) | 2009-01-23 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2010086089A1 (de) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metallkomplexe |
DE102009009277A1 (de) | 2009-02-17 | 2010-08-19 | Merck Patent Gmbh | Organische elektronische Vorrichtung |
DE102009010714A1 (de) | 2009-02-27 | 2010-09-02 | Merck Patent Gmbh | Vernetzbare und vernetzte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung |
WO2010097155A1 (de) | 2009-02-27 | 2010-09-02 | Merck Patent Gmbh | Polymer mit aldehydgruppen, umsetzung sowie vernetzung dieses polymers, vernetztes polymer sowie elektrolumineszenzvorrichtung enthaltend dieses polymer |
DE102009010713A1 (de) | 2009-02-27 | 2010-09-02 | Merck Patent Gmbh | Polymer mit Aldehydgruppen, Umsetzung sowie Vernetzung dieses Polymers, vernetztes Polymer sowie Elektrolumineszenzvorrichtung enthaltend dieses Polymer |
WO2010099852A1 (de) | 2009-03-02 | 2010-09-10 | Merck Patent Gmbh | Metallkomplexe mit azaborol-liganden und elektronische vorrichtung damit |
WO2010102709A1 (de) | 2009-03-13 | 2010-09-16 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2010136110A2 (de) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Polymere, die substituierte indenofluorenderivate als struktureinheit enthalten, verfahren zu deren herstellung sowie deren verwendung |
DE102009030847A1 (de) | 2009-06-26 | 2010-12-30 | Merck Patent Gmbh | Polymere enthaltend substituierte Anthracenyleinheiten, Blends enthaltend diese Polymere sowie Vorrichtungen enthaltend diese Polymere oder Blends |
DE102009031021A1 (de) | 2009-06-30 | 2011-01-05 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2011009522A2 (de) | 2009-07-22 | 2011-01-27 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2011012212A1 (de) | 2009-07-27 | 2011-02-03 | Merck Patent Gmbh | Neue materialien für organische elektrolumineszenzvorrichtungen |
DE102009030848A1 (de) | 2009-06-26 | 2011-02-03 | Merck Patent Gmbh | Polymere enthaltend Struktureinheiten, die Alkylalkoxygruppen aufweisen, Blends enthaltend diese Polymere sowie optoelektronische Vorrichtungen enthaltend diese Polymere und Blends |
DE102009042693A1 (de) | 2009-09-23 | 2011-03-24 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
WO2011032686A1 (de) | 2009-09-16 | 2011-03-24 | Merck Patent Gmbh | Formulierungen zur herstellung von elektronischen vorrichtungen |
WO2011042107A2 (de) | 2009-10-08 | 2011-04-14 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102009049587A1 (de) | 2009-10-16 | 2011-04-21 | Merck Patent Gmbh | Metallkomplexe |
WO2011054442A2 (de) | 2009-11-06 | 2011-05-12 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
DE102009052428A1 (de) | 2009-11-10 | 2011-05-12 | Merck Patent Gmbh | Verbindung für elektronische Vorrichtungen |
DE102009033371A1 (de) | 2009-07-16 | 2011-05-12 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009053382A1 (de) | 2009-11-14 | 2011-05-19 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009053644A1 (de) | 2009-11-17 | 2011-05-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009053836A1 (de) | 2009-11-18 | 2011-05-26 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009023154A1 (de) | 2009-05-29 | 2011-06-16 | Merck Patent Gmbh | Zusammensetzung, enthaltend mindestens eine Emitterverbindung und mindestens ein Polymer mit konjugationsunterbrechenden Einheiten |
DE102009059985A1 (de) | 2009-12-22 | 2011-07-07 | Merck Patent GmbH, 64293 | Polymer mit Aldehydgruppen, Umsetzung sowie Vernetzung dieses Polymers, vernetztes Polymer sowie Elektrolumineszenzvorrichtung enthaltend dieses Polymer |
DE102010004803A1 (de) | 2010-01-16 | 2011-07-21 | Merck Patent GmbH, 64293 | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010005697A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent GmbH, 64293 | Verbindungen für elektronische Vorrichtungen |
WO2011091838A1 (de) | 2010-01-29 | 2011-08-04 | Merck Patent Gmbh | Styrolbasierte copolymere, insbesondere für die anwendung in optoelektronischen bauteilen |
WO2011098205A1 (de) | 2010-02-12 | 2011-08-18 | Merck Patent Gmbh | Elektrolumineszierende polymere, verfahren zu ihrer herstellung sowie ihre verwendung |
DE102010009903A1 (de) | 2010-03-02 | 2011-09-08 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
WO2011110277A1 (en) | 2010-03-11 | 2011-09-15 | Merck Patent Gmbh | Fibers in therapy and cosmetics |
WO2011116857A1 (en) | 2010-03-23 | 2011-09-29 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
DE102010012738A1 (de) | 2010-03-25 | 2011-09-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2011128017A1 (de) | 2010-04-14 | 2011-10-20 | Merck Patent Gmbh | Überbrückte triarylamine und -phosphine als materialien für elektronische vorrichtungen |
DE102010019306A1 (de) | 2010-05-04 | 2011-11-10 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
WO2011137922A1 (de) | 2010-05-03 | 2011-11-10 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
DE102009022858A1 (de) | 2009-05-27 | 2011-12-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
DE102010024335A1 (de) | 2010-06-18 | 2011-12-22 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
DE102010024542A1 (de) | 2010-06-22 | 2011-12-22 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102010024897A1 (de) | 2010-06-24 | 2011-12-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010027320A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Polymere Materialien für organische Elektrolumineszenzvorrichtungen |
WO2012007087A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metallkomplexe |
WO2012013310A1 (de) | 2010-07-29 | 2012-02-02 | Merck Patent Gmbh | Polymere enthaltend substituierte benzodithiopheneinheiten, blends enthaltend diese polymere sowie vorrichtungen enthaltend diese polymere oder blends |
DE102010033080A1 (de) | 2010-08-02 | 2012-02-02 | Merck Patent Gmbh | Polymere mit Struktureinheiten, die Elektronen-Transport-Eigenschaften aufweisen |
WO2012016630A1 (de) | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
DE102010045369A1 (de) | 2010-09-14 | 2012-03-15 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010048608A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010048498A1 (de) | 2010-10-14 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2012048780A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012084114A1 (de) | 2010-12-23 | 2012-06-28 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
DE102010056151A1 (de) | 2010-12-28 | 2012-06-28 | Merck Patent Gmbh | Materiallen für organische Elektrolumineszenzvorrichtungen |
WO2012095143A1 (de) | 2011-01-13 | 2012-07-19 | Merck Patent Gmbh | Verbindungen für organische elektrolumineszenzvorrichtungen |
DE102012000064A1 (de) | 2011-01-21 | 2012-07-26 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
EP2482159A2 (de) | 2011-01-28 | 2012-08-01 | Honeywell International, Inc. | Verfahren und umkonfigurierbare System zur Optimierung der Leistung eines zustandsabhängigen Wartungssystems |
DE102011010841A1 (de) | 2011-02-10 | 2012-08-16 | Merck Patent Gmbh | (1,3)-Dioxan-5-on-Verbindungen |
DE102011011539A1 (de) | 2011-02-17 | 2012-08-23 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
WO2012139693A1 (de) | 2011-04-13 | 2012-10-18 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012139692A1 (de) | 2011-04-13 | 2012-10-18 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2012143079A1 (de) | 2011-04-18 | 2012-10-26 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012149999A1 (de) | 2011-05-05 | 2012-11-08 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012150001A1 (de) | 2011-05-05 | 2012-11-08 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012149992A1 (de) | 2011-05-04 | 2012-11-08 | Merck Patent Gmbh | Vorrichtung zur aufbewahrung von frischwaren |
WO2012171609A1 (de) | 2011-06-17 | 2012-12-20 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2013017192A1 (de) | 2011-08-03 | 2013-02-07 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2013017189A1 (de) | 2011-07-29 | 2013-02-07 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
DE102011116165A1 (de) | 2011-10-14 | 2013-04-18 | Merck Patent Gmbh | Benzodioxepin-3-on-Verbindungen |
WO2013060411A1 (de) | 2011-10-28 | 2013-05-02 | Merck Patent Gmbh | Hyperverzweigte polymere, verfahren zu deren herstellung sowie deren verwendung in elektronischen vorrichtungen |
WO2013060418A1 (en) | 2011-10-27 | 2013-05-02 | Merck Patent Gmbh | Materials for electronic devices |
WO2013083216A1 (de) | 2011-11-17 | 2013-06-13 | Merck Patent Gmbh | Spiro -dihydroacridinderivate und ihre verwendung als materialien für organische elektrolumineszenzvorrichtungen |
WO2013087142A1 (de) | 2011-12-12 | 2013-06-20 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
DE102012022880A1 (de) | 2011-12-22 | 2013-06-27 | Merck Patent Gmbh | Elektronische Vorrichtungen enthaltend organische Schichten |
WO2013120577A1 (en) | 2012-02-14 | 2013-08-22 | Merck Patent Gmbh | Spirobifluorene compounds for organic electroluminescent devices |
WO2013124029A2 (de) | 2012-02-22 | 2013-08-29 | Merck Patent Gmbh | Polymere enthaltend dibenzocycloheptan-struktureinheiten |
WO2013139431A1 (de) | 2012-03-23 | 2013-09-26 | Merck Patent Gmbh | 9,9'-spirobixanthenderivate für elektrolumineszenzvorrichtungen |
WO2013156129A1 (de) | 2012-04-17 | 2013-10-24 | Merck Patent Gmbh | Polymere enthaltend substituierte oligo-triarylamin-einheiten sowie elektrolumineszenzvorrichtungen enthaltend diese polymere |
WO2013174471A1 (en) | 2012-05-24 | 2013-11-28 | Merck Patent Gmbh | Metal complexes comprising condensed heteroaromatic rings |
WO2013182263A1 (de) | 2012-06-06 | 2013-12-12 | Merck Patent Gmbh | Phenanthrenverbindungen für organische elektronische vorrichtungen |
WO2014000860A1 (de) | 2012-06-29 | 2014-01-03 | Merck Patent Gmbh | Polymere enthaltend 2,7-pyren-struktureinheiten |
WO2014008982A1 (de) | 2012-07-13 | 2014-01-16 | Merck Patent Gmbh | Metallkomplexe |
US8637853B2 (en) | 2007-10-24 | 2014-01-28 | Merck Patent Gmbh | Optoelectronic device |
WO2014015938A1 (de) | 2012-07-23 | 2014-01-30 | Merck Patent Gmbh | Derivate von 2-diarylaminofluoren und diese enthaltnde organische elektronische verbindungen |
WO2014015937A1 (de) | 2012-07-23 | 2014-01-30 | Merck Patent Gmbh | Verbindungen und organische elektrolumineszierende vorrichtungen |
WO2014015935A2 (de) | 2012-07-23 | 2014-01-30 | Merck Patent Gmbh | Verbindungen und organische elektronische vorrichtungen |
WO2014023377A2 (de) | 2012-08-07 | 2014-02-13 | Merck Patent Gmbh | Metallkomplexe |
WO2014044347A1 (de) | 2012-09-20 | 2014-03-27 | Merck Patent Gmbh | Metallkomplexe |
WO2014082705A1 (de) | 2012-11-30 | 2014-06-05 | Merck Patent Gmbh | Elektronische vorrichtung |
WO2014101981A1 (en) | 2012-12-28 | 2014-07-03 | Merck Patent Gmbh | Composition comprising polymeric organic semiconducting compounds |
WO2014106524A2 (de) | 2013-01-03 | 2014-07-10 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2014106522A1 (de) | 2013-01-03 | 2014-07-10 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
US8865321B2 (en) | 2008-11-11 | 2014-10-21 | Merck Patent Gmbh | Organic electroluminescent devices |
WO2015086108A1 (de) | 2013-12-12 | 2015-06-18 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2015090504A2 (de) | 2013-12-19 | 2015-06-25 | Merck Patent Gmbh | Heterocyclische spiroverbindungen |
US9136475B2 (en) | 2010-12-24 | 2015-09-15 | Joled Inc. | Organic EL element and method for producing same |
WO2016034262A1 (de) | 2014-09-05 | 2016-03-10 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
WO2016074755A1 (de) | 2014-11-11 | 2016-05-19 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2016107663A1 (de) | 2014-12-30 | 2016-07-07 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
WO2016119992A1 (en) | 2015-01-30 | 2016-08-04 | Merck Patent Gmbh | Materials for electronic devices |
WO2016120007A1 (en) | 2015-01-30 | 2016-08-04 | Merck Patent Gmbh | Formulations with a low particle content |
WO2016124304A1 (de) | 2015-02-03 | 2016-08-11 | Merck Patent Gmbh | Metallkomplexe |
WO2016155866A1 (en) | 2015-03-30 | 2016-10-06 | Merck Patent Gmbh | Formulation of an organic functional material comprising a siloxane solvent |
EP1745113B1 (de) * | 2004-05-11 | 2016-10-26 | Merck Patent GmbH | Neue materialmischungen für die elektrolumineszenz |
WO2016198141A1 (en) | 2015-06-12 | 2016-12-15 | Merck Patent Gmbh | Esters containing non-aromatic cycles as solvents for oled formulations |
WO2016198144A1 (en) | 2015-06-10 | 2016-12-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2017008883A1 (en) | 2015-07-15 | 2017-01-19 | Merck Patent Gmbh | Composition comprising organic semiconducting compounds |
WO2017012687A1 (en) | 2015-07-22 | 2017-01-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2017012694A1 (en) | 2015-07-23 | 2017-01-26 | Merck Patent Gmbh | Phenyl derivatives substituted with at least two electron acceptors and at least two electron donors for use in organic electronic devices |
WO2017016630A1 (en) | 2015-07-30 | 2017-02-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2017028940A1 (en) | 2015-08-14 | 2017-02-23 | Merck Patent Gmbh | Phenoxazine derivatives for organic electroluminescent devices |
WO2017036572A1 (en) | 2015-08-28 | 2017-03-09 | Merck Patent Gmbh | Formulation of an organic functional material comprising an epoxy group containing solvent |
WO2017036573A1 (en) | 2015-08-28 | 2017-03-09 | Merck Patent Gmbh | Compounds for electronic devices |
WO2017097391A1 (en) | 2015-12-10 | 2017-06-15 | Merck Patent Gmbh | Formulations containing ketones comprising non-aromatic cycles |
WO2017102049A1 (en) | 2015-12-16 | 2017-06-22 | Merck Patent Gmbh | Formulations containing a mixture of at least two different solvents |
WO2017102048A1 (en) | 2015-12-15 | 2017-06-22 | Merck Patent Gmbh | Esters containing aromatic groups as solvents for organic electronic formulations |
WO2017102052A1 (en) | 2015-12-16 | 2017-06-22 | Merck Patent Gmbh | Formulations containing a solid solvent |
WO2017133829A1 (de) | 2016-02-05 | 2017-08-10 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2017140404A1 (en) | 2016-02-17 | 2017-08-24 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2017157983A1 (de) | 2016-03-17 | 2017-09-21 | Merck Patent Gmbh | Verbindungen mit spirobifluoren-strukturen |
DE102016003104A1 (de) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter |
WO2017178311A1 (de) | 2016-04-11 | 2017-10-19 | Merck Patent Gmbh | Heterocyclische verbindungen mit dibenzofuran- und/oder dibenzothiophen-strukturen |
WO2017207596A1 (en) | 2016-06-03 | 2017-12-07 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2017216128A1 (en) | 2016-06-17 | 2017-12-21 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2017216129A1 (en) | 2016-06-16 | 2017-12-21 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018001990A1 (de) | 2016-06-30 | 2018-01-04 | Merck Patent Gmbh | Verfahren zur auftrennung von enantiomerenmischungen von metallkomplexen |
WO2018001928A1 (en) | 2016-06-28 | 2018-01-04 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018007421A1 (en) | 2016-07-08 | 2018-01-11 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2018011186A1 (de) | 2016-07-14 | 2018-01-18 | Merck Patent Gmbh | Metallkomplexe |
WO2018024719A1 (en) | 2016-08-04 | 2018-02-08 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018050583A1 (de) | 2016-09-14 | 2018-03-22 | Merck Patent Gmbh | Verbindungen mit carbazol-strukturen |
WO2018050584A1 (de) | 2016-09-14 | 2018-03-22 | Merck Patent Gmbh | Verbindungen mit spirobifluoren-strukturen |
WO2018060218A1 (de) | 2016-09-30 | 2018-04-05 | Merck Patent Gmbh | Carbazole mit diazadibenzofuran- oder diazadibenzothiophen-strukturen |
WO2018060307A1 (de) | 2016-09-30 | 2018-04-05 | Merck Patent Gmbh | Verbindungen mit diazadibenzofuran- oder diazadibenzothiophen-strukturen |
WO2018069167A1 (de) | 2016-10-10 | 2018-04-19 | Merck Patent Gmbh | Elektronische vorrichtung |
WO2018077660A1 (en) | 2016-10-31 | 2018-05-03 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018077662A1 (en) | 2016-10-31 | 2018-05-03 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018083053A1 (de) | 2016-11-02 | 2018-05-11 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2018087346A1 (de) | 2016-11-14 | 2018-05-17 | Merck Patent Gmbh | Verbindungen mit einer akzeptor- und einer donorgruppe |
WO2018087020A1 (en) | 2016-11-08 | 2018-05-17 | Merck Patent Gmbh | Compounds for electronic devices |
WO2018095839A1 (de) | 2016-11-22 | 2018-05-31 | Merck Patent Gmbh | Verbrückte triarylamine für elektronische vorrichtungen |
WO2018095888A1 (en) | 2016-11-25 | 2018-05-31 | Merck Patent Gmbh | Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
WO2018095940A1 (en) | 2016-11-25 | 2018-05-31 | Merck Patent Gmbh | Bisbenzofuran-fused indeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
WO2018099846A1 (de) | 2016-11-30 | 2018-06-07 | Merck Patent Gmbh | Verbindungen mit valerolaktam-strukturen |
WO2018099847A1 (de) | 2016-11-30 | 2018-06-07 | Merck Patent Gmbh | Polymere mit asymmetrischen wiederholungseinheiten |
WO2018104195A1 (de) | 2016-12-05 | 2018-06-14 | Merck Patent Gmbh | Stickstoffhaltige heterocyclen zur verwendung in oleds |
WO2018104202A1 (en) | 2016-12-06 | 2018-06-14 | Merck Patent Gmbh | Preparation process for an electronic device |
WO2018108760A1 (en) | 2016-12-13 | 2018-06-21 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018114883A1 (de) | 2016-12-22 | 2018-06-28 | Merck Patent Gmbh | Mischungen umfassend mindestens zwei organisch funktionelle verbindungen |
EP3345984A1 (de) | 2013-12-06 | 2018-07-11 | Merck Patent GmbH | Verbindungen und organische elektronische vorrichtungen |
WO2018134392A1 (en) | 2017-01-23 | 2018-07-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2018138319A1 (en) | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Method for forming an organic electroluminescence (el) element |
WO2018138039A1 (de) | 2017-01-25 | 2018-08-02 | Merck Patent Gmbh | Carbazolderivate |
WO2018138318A1 (en) | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Method for forming an organic element of an electronic device |
WO2018141706A1 (de) | 2017-02-02 | 2018-08-09 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2018157981A1 (de) | 2017-03-02 | 2018-09-07 | Merck Patent Gmbh | Materialien für organische elektronische vorrichtungen |
WO2018166932A1 (de) | 2017-03-13 | 2018-09-20 | Merck Patent Gmbh | Verbindungen mit arylamin-strukturen |
EP3378857A1 (de) | 2012-11-12 | 2018-09-26 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
WO2018178136A1 (en) | 2017-03-31 | 2018-10-04 | Merck Patent Gmbh | Printing method for an organic light emitting diode (oled) |
WO2018189050A1 (en) | 2017-04-10 | 2018-10-18 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018197447A1 (de) | 2017-04-25 | 2018-11-01 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2018202603A1 (en) | 2017-05-03 | 2018-11-08 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018215318A1 (de) | 2017-05-22 | 2018-11-29 | Merck Patent Gmbh | Hexazyklische heteroaromatische verbindungen für elektronische vorrichtungen |
WO2018234346A1 (en) | 2017-06-23 | 2018-12-27 | Merck Patent Gmbh | MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES |
WO2018234220A1 (de) | 2017-06-21 | 2018-12-27 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2019002190A1 (en) | 2017-06-28 | 2019-01-03 | Merck Patent Gmbh | MATERIALS FOR ELECTRONIC DEVICES |
WO2019007823A1 (en) | 2017-07-03 | 2019-01-10 | Merck Patent Gmbh | LOW-PHENOL IMPURITY FORMULATIONS |
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WO2019115573A1 (en) | 2017-12-15 | 2019-06-20 | Merck Patent Gmbh | Formulation of an organic functional material |
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WO2019121483A1 (en) | 2017-12-20 | 2019-06-27 | Merck Patent Gmbh | Heteroaromatic compounds |
WO2019162483A1 (en) | 2018-02-26 | 2019-08-29 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2019175149A1 (en) | 2018-03-16 | 2019-09-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2019238782A1 (en) | 2018-06-15 | 2019-12-19 | Merck Patent Gmbh | Formulation of an organic functional material |
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WO2020212295A1 (en) | 2019-04-16 | 2020-10-22 | Merck Patent Gmbh | Formulation containing a crosslinkable polymer |
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WO2024115426A1 (de) | 2022-12-01 | 2024-06-06 | Merck Patent Gmbh | Polymere enthaltend spirotruxenderivate als wiederholungseinheit sowie elektrolumineszenzvorrichtungen enthaltend diese polymere |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE517905T1 (de) * | 2004-06-26 | 2011-08-15 | Merck Patent Gmbh | Verbindungen für organische elektronische vorrichtungen |
DE102005022903A1 (de) * | 2005-05-18 | 2006-11-23 | Merck Patent Gmbh | Lösungen organischer Halbleiter |
JP5328097B2 (ja) * | 2005-11-11 | 2013-10-30 | キヤノン株式会社 | スルホン酸基又はスルホン酸エステル基と、アミド基とを有するポリマー、及び該ポリマーを有する静電荷像現像トナー |
DE102006003710A1 (de) * | 2006-01-26 | 2007-08-02 | Merck Patent Gmbh | Elektrolumineszierende Materialien und deren Verwendung |
DE102006006412A1 (de) * | 2006-02-13 | 2007-08-16 | Merck Patent Gmbh | Elektronisches Bauteil, Verfahren zu dessen Herstellung und dessen Verwendung |
DE102006031991A1 (de) * | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Elektrolumineszierende Polymere und ihre Verwendung |
WO2009063757A1 (ja) * | 2007-11-14 | 2009-05-22 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置 |
WO2009155595A2 (en) * | 2008-06-20 | 2009-12-23 | Tempur-Pedic Management, Inc. | Inflatable mattress and method of operating same |
DE102008049037A1 (de) * | 2008-09-25 | 2010-04-22 | Merck Patent Gmbh | Neue Polymere mit niedriger Polydispersität |
KR101027582B1 (ko) * | 2008-12-06 | 2011-04-06 | 대주전자재료 주식회사 | 포스핀 옥사이드계 화합물 및 이를 이용한 유기 전기발광 소자 |
EP3156472B1 (de) * | 2015-10-16 | 2019-12-04 | Karlsruher Institut für Technologie | Neues medium zur tta-photon-aufwärtsumsetzung in polymerer host-matrix |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020028347A1 (en) * | 2000-06-12 | 2002-03-07 | Marrocco Matthew L. | Polymer matrix electroluminescent materials and devices |
WO2002077060A1 (de) * | 2001-03-24 | 2002-10-03 | Covion Organic Semiconductors Gmbh | Konjugierte polymere enthaltend spirobifluoren-einheiten und fluoren-einheiten und deren verwendung |
WO2003020790A2 (de) * | 2001-09-04 | 2003-03-13 | Covion Organic Semiconductors Gmbh | Konjugierte polymere enthaltend spirobifluoren-einheiten und deren verwendung |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3022908A (en) | 1960-04-18 | 1962-02-27 | Flexible Sewertool Corp | Drag bucket dredging and dumping mechanism for culverts and the like |
US3224208A (en) | 1961-11-24 | 1965-12-21 | Conch Int Methane Ltd | Purification of natural gases |
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
EP1027398B1 (de) | 1997-10-23 | 2004-06-09 | Isis Innovation Limited | Lichtemittierende dendrimere |
GB0002936D0 (en) | 2000-02-09 | 2000-03-29 | Isis Innovation | Improved dendrimers |
DE10019291C2 (de) | 2000-04-19 | 2002-04-04 | Sueddeutsche Kalkstickstoff | 2-Alkoxy-5-methoxypyrimidine bzw. deren tautomere Formen sowie Verfahren zu deren Herstellung |
WO2001091203A2 (en) * | 2000-05-22 | 2001-11-29 | Showa Denko K. K. | Organic electroluminescent device and light-emitting material |
JP4876333B2 (ja) * | 2000-06-08 | 2012-02-15 | 東レ株式会社 | 発光素子 |
US7592074B2 (en) | 2001-02-20 | 2009-09-22 | Isis Innovation Limited | Metal-containing dendrimers |
DE10109027A1 (de) | 2001-02-24 | 2002-09-05 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
JP2002260863A (ja) * | 2001-03-05 | 2002-09-13 | Fuji Xerox Co Ltd | 有機電界発光素子 |
US6949621B2 (en) * | 2001-03-08 | 2005-09-27 | Japan Science And Technology Corporation | Polymer containing 9-oxo-9-phosphafluorene-2,7-diyl skeleton in backbone and process for producing the same |
JP4438042B2 (ja) | 2001-03-08 | 2010-03-24 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
DE10116962A1 (de) | 2001-04-05 | 2002-10-10 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
US7056846B2 (en) | 2001-12-04 | 2006-06-06 | 3M Innovative Properties Company | Repellent fluorochemical compositions |
DE10159946A1 (de) | 2001-12-06 | 2003-06-18 | Covion Organic Semiconductors | Prozess zur Herstellung von Aryl-Aryl gekoppelten Verbindungen |
JP3890242B2 (ja) * | 2002-03-26 | 2007-03-07 | キヤノン株式会社 | 高分子化合物及び電界発光素子 |
JP4103442B2 (ja) * | 2002-04-25 | 2008-06-18 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子および表示装置 |
WO2003099901A1 (fr) | 2002-05-28 | 2003-12-04 | Sumitomo Chemical Company, Limited | Polymere et element luminescent polymere contenant ce polymere |
JP4207667B2 (ja) | 2002-05-28 | 2009-01-14 | 住友化学株式会社 | 高分子化合物およびそれを用いた高分子発光素子 |
DE10238903A1 (de) | 2002-08-24 | 2004-03-04 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
DE10241814A1 (de) | 2002-09-06 | 2004-03-25 | Covion Organic Semiconductors Gmbh | Prozeß zur Herstellung von Aryl-Aryl gekoppelten Verbindungen |
DE10249723A1 (de) | 2002-10-25 | 2004-05-06 | Covion Organic Semiconductors Gmbh | Arylamin-Einheiten enthaltende konjugierte Polymere, deren Darstellung und Verwendung |
JP4461762B2 (ja) * | 2002-10-30 | 2010-05-12 | 住友化学株式会社 | 高分子化合物およびそれを用いた高分子発光素子 |
DE10304819A1 (de) | 2003-02-06 | 2004-08-19 | Covion Organic Semiconductors Gmbh | Carbazol-enthaltende konjugierte Polymere und Blends, deren Darstellung und Verwendung |
JP4590825B2 (ja) * | 2003-02-21 | 2010-12-01 | コニカミノルタホールディングス株式会社 | 白色発光有機エレクトロルミネッセンス素子 |
EP1618170A2 (de) * | 2003-04-15 | 2006-01-25 | Covion Organic Semiconductors GmbH | Mischungen von organischen zur emission befähigten halbleitern und matrixmaterialien, deren verwendung und elektronikbauteile enthaltend diese mischungen |
DE10317556B4 (de) | 2003-04-15 | 2021-05-12 | Merck Patent Gmbh | Mischungen von organischen zur Emission befähigten Halbleitern und Matrixmaterialien, deren Verwendung und Elektronikbauteile enthaltend diese |
DE10328627A1 (de) | 2003-06-26 | 2005-02-17 | Covion Organic Semiconductors Gmbh | Neue Materialien für die Elektrolumineszenz |
DE10330761A1 (de) | 2003-07-07 | 2005-02-03 | Covion Organic Semiconductors Gmbh | Mischungen von organischen zur Emission befähigten Halbleitern und Matrixmaterialien, deren Verwendung und Elektronikbauteile enthaltend dieses |
WO2005003253A2 (de) * | 2003-07-07 | 2005-01-13 | Covion Organic Semiconductors Gmbh | Mischungen von organischen zur emission befähigten halbleitern und matrixmaterialen, deren verwendung und elektronikbauteile enthaltend diese |
DE10337346A1 (de) | 2003-08-12 | 2005-03-31 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung |
EP1668718B1 (de) * | 2003-09-19 | 2009-03-25 | MERCK PATENT GmbH | Organisches elektrolumineszenzelement |
DE10343606A1 (de) | 2003-09-20 | 2005-04-14 | Covion Organic Semiconductors Gmbh | Weiß emittierende Copolymere, deren Darstellung und Verwendung |
DE10350606A1 (de) | 2003-10-30 | 2005-06-09 | Covion Organic Semiconductors Gmbh | Verfahren zur Herstellung heteroleptischer, ortho-metallierter Organometall-Verbindungen |
-
2004
- 2004-10-21 EP EP04790695.3A patent/EP1675930B1/de not_active Not-in-force
- 2004-10-21 US US10/576,920 patent/US7659540B2/en not_active Expired - Fee Related
- 2004-10-21 EP EP10015929.2A patent/EP2366752B1/de not_active Not-in-force
- 2004-10-21 WO PCT/EP2004/011888 patent/WO2005040302A1/de active Application Filing
- 2004-10-21 JP JP2006536042A patent/JP2007517079A/ja active Pending
-
2006
- 2006-04-20 KR KR1020067007587A patent/KR101215160B1/ko active IP Right Grant
-
2009
- 2009-12-16 US US12/639,591 patent/US8173276B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020028347A1 (en) * | 2000-06-12 | 2002-03-07 | Marrocco Matthew L. | Polymer matrix electroluminescent materials and devices |
WO2002077060A1 (de) * | 2001-03-24 | 2002-10-03 | Covion Organic Semiconductors Gmbh | Konjugierte polymere enthaltend spirobifluoren-einheiten und fluoren-einheiten und deren verwendung |
WO2003020790A2 (de) * | 2001-09-04 | 2003-03-13 | Covion Organic Semiconductors Gmbh | Konjugierte polymere enthaltend spirobifluoren-einheiten und deren verwendung |
Non-Patent Citations (1)
Title |
---|
V. CLEAVE ET.AL.: "Harvesting singlet and triplet energy in polymer LEDs", ADV. MATER., vol. 11, no. 4, 1999, pages 285 - 288, XP002316107 * |
Cited By (355)
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US7776455B2 (en) | 2004-02-20 | 2010-08-17 | Merck Patent Gmbh | Organic electronic devices |
WO2005084082A1 (de) * | 2004-02-20 | 2005-09-09 | Merck Patent Gmbh | Organische elektronische vorrichtungen |
EP1745113B1 (de) * | 2004-05-11 | 2016-10-26 | Merck Patent GmbH | Neue materialmischungen für die elektrolumineszenz |
WO2007022845A1 (de) | 2005-08-26 | 2007-03-01 | Merck Patent Gmbh | Neue materialien für organische elektrolumineszenzvorrichtungen |
EP3211058A1 (de) | 2005-08-26 | 2017-08-30 | Merck Patent GmbH | Neue materialien für organische elektrolumineszenzvorrichtungen |
JP2007087786A (ja) * | 2005-09-22 | 2007-04-05 | Toppan Printing Co Ltd | 有機エレクトロルミネッセンスインキ及びこれを用いた有機エレクトロルミネッセンス素子の製造方法 |
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US7799875B2 (en) | 2005-12-17 | 2010-09-21 | Merck Patent Gmbh | Triarylamine-arylvinylene moiety-containing conjugated polymers, their production and use |
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WO2007081058A1 (ja) * | 2006-01-16 | 2007-07-19 | Sumitomo Chemical Company, Limited | 高分子化合物およびそれを用いた高分子発光素子 |
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US8637853B2 (en) | 2007-10-24 | 2014-01-28 | Merck Patent Gmbh | Optoelectronic device |
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DE102008027005A1 (de) | 2008-06-05 | 2009-12-10 | Merck Patent Gmbh | Organische elektronische Vorrichtung enthaltend Metallkomplexe |
DE102008033943A1 (de) | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008044868A1 (de) | 2008-08-29 | 2010-03-04 | Merck Patent Gmbh | Elektrolumineszierende Polymere, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
US8580395B2 (en) | 2008-08-29 | 2013-11-12 | Merck Patent Gmbh | Electroluminescent polymers, method for the production thereof, and use thereof |
DE102008045662A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Optoelektronische Vorrichtung |
DE102008045663A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Fluorverbrückte Assoziate für optoelektronische Anwendungen |
DE102008045664A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Optoelektronische Vorrichtung |
DE102008050841A1 (de) | 2008-10-08 | 2010-04-15 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008050841B4 (de) | 2008-10-08 | 2019-08-01 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US8637168B2 (en) | 2008-10-08 | 2014-01-28 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
DE102008054141A1 (de) | 2008-10-31 | 2010-05-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US8865321B2 (en) | 2008-11-11 | 2014-10-21 | Merck Patent Gmbh | Organic electroluminescent devices |
DE102008056688A1 (de) | 2008-11-11 | 2010-05-12 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US8597798B2 (en) | 2008-11-13 | 2013-12-03 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
DE102008057051A1 (de) | 2008-11-13 | 2010-05-20 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008057050A1 (de) | 2008-11-13 | 2010-05-20 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009005289A1 (de) | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2010083872A2 (de) | 2009-01-20 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102009005289B4 (de) | 2009-01-20 | 2023-06-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen, Verfahren zu deren Herstellung und elektronische Vorrichtungen, enthaltend diese |
DE102009005288A1 (de) | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2010083873A1 (de) | 2009-01-20 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
US9475792B2 (en) | 2009-01-20 | 2016-10-25 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
US8710284B2 (en) | 2009-01-23 | 2014-04-29 | Merck Patent Gmbh | Materials for organic electroluminescent devices containing substituted 10-benzo[c]phenanthrenes |
WO2010083869A2 (de) | 2009-01-23 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102009005746A1 (de) | 2009-01-23 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US9006503B2 (en) | 2009-01-23 | 2015-04-14 | Merck Patent Gmbh | Organic electroluminescence devices containing substituted benzo[C]phenanthrenes |
WO2010086089A1 (de) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metallkomplexe |
US9169282B2 (en) | 2009-02-02 | 2015-10-27 | Merck Patent Gmbh | Metal complexes |
DE102009007038A1 (de) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metallkomplexe |
WO2010094378A1 (de) | 2009-02-17 | 2010-08-26 | Merck Patent Gmbh | Organische elektronische vorrichtung |
DE102009009277A1 (de) | 2009-02-17 | 2010-08-19 | Merck Patent Gmbh | Organische elektronische Vorrichtung |
US9066410B2 (en) | 2009-02-17 | 2015-06-23 | Merck Patent Gmbh | Organic electronic device |
US9315617B2 (en) | 2009-02-27 | 2016-04-19 | Merck Patent Gmbh | Crosslinkable and crosslinked polymers, method for the production thereof, and use thereof |
US9728724B2 (en) | 2009-02-27 | 2017-08-08 | Merck Patent Gmbh | Polymer containing aldehyde groups, reaction and crosslinking of this polymer, crosslinked polymer, and electroluminescent device comprising this polymer |
DE102009010714A1 (de) | 2009-02-27 | 2010-09-02 | Merck Patent Gmbh | Vernetzbare und vernetzte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung |
WO2010097156A1 (de) | 2009-02-27 | 2010-09-02 | Merck Patent Gmbh | Vernetzbare und vernetzte polymere, verfahren zu deren herstellung sowie deren verwendung |
WO2010097155A1 (de) | 2009-02-27 | 2010-09-02 | Merck Patent Gmbh | Polymer mit aldehydgruppen, umsetzung sowie vernetzung dieses polymers, vernetztes polymer sowie elektrolumineszenzvorrichtung enthaltend dieses polymer |
US9156939B2 (en) | 2009-02-27 | 2015-10-13 | Merck Patent Gmbh | Polymer containing aldehyde groups, reaction and crosslinking of this polymer, crosslinked polymer, and electroluminescent device comprising this polymer |
DE102009010713A1 (de) | 2009-02-27 | 2010-09-02 | Merck Patent Gmbh | Polymer mit Aldehydgruppen, Umsetzung sowie Vernetzung dieses Polymers, vernetztes Polymer sowie Elektrolumineszenzvorrichtung enthaltend dieses Polymer |
US9074128B2 (en) | 2009-03-02 | 2015-07-07 | Merck Patent Gmbh | Metal complexes having azaborol ligands and electronic device having the same |
WO2010099852A1 (de) | 2009-03-02 | 2010-09-10 | Merck Patent Gmbh | Metallkomplexe mit azaborol-liganden und elektronische vorrichtung damit |
DE102009011223A1 (de) | 2009-03-02 | 2010-09-23 | Merck Patent Gmbh | Metallkomplexe |
WO2010102709A1 (de) | 2009-03-13 | 2010-09-16 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102009013041A1 (de) | 2009-03-13 | 2010-09-16 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US9085579B2 (en) | 2009-03-13 | 2015-07-21 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
DE102009022858A1 (de) | 2009-05-27 | 2011-12-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
DE102009023154A1 (de) | 2009-05-29 | 2011-06-16 | Merck Patent Gmbh | Zusammensetzung, enthaltend mindestens eine Emitterverbindung und mindestens ein Polymer mit konjugationsunterbrechenden Einheiten |
WO2010136110A2 (de) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Polymere, die substituierte indenofluorenderivate als struktureinheit enthalten, verfahren zu deren herstellung sowie deren verwendung |
DE102009023156A1 (de) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Polymere, die substituierte Indenofluorenderivate als Struktureinheit enthalten, Verfahren zu deren Herstellung sowie deren Verwendung |
DE102009030847A1 (de) | 2009-06-26 | 2010-12-30 | Merck Patent Gmbh | Polymere enthaltend substituierte Anthracenyleinheiten, Blends enthaltend diese Polymere sowie Vorrichtungen enthaltend diese Polymere oder Blends |
US8557953B2 (en) | 2009-06-26 | 2013-10-15 | Merck Patent Gmbh | Polymers comprising substituted anthracenyl units, blends comprising these polymers, and devices comprising these polymers or blends |
DE102009030848A1 (de) | 2009-06-26 | 2011-02-03 | Merck Patent Gmbh | Polymere enthaltend Struktureinheiten, die Alkylalkoxygruppen aufweisen, Blends enthaltend diese Polymere sowie optoelektronische Vorrichtungen enthaltend diese Polymere und Blends |
WO2011000455A1 (de) | 2009-06-30 | 2011-01-06 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102009031021A1 (de) | 2009-06-30 | 2011-01-05 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009033371A1 (de) | 2009-07-16 | 2011-05-12 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
WO2011009522A2 (de) | 2009-07-22 | 2011-01-27 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
DE102009034194A1 (de) | 2009-07-22 | 2011-01-27 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
WO2011012212A1 (de) | 2009-07-27 | 2011-02-03 | Merck Patent Gmbh | Neue materialien für organische elektrolumineszenzvorrichtungen |
DE102009034625A1 (de) | 2009-07-27 | 2011-02-03 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
WO2011032686A1 (de) | 2009-09-16 | 2011-03-24 | Merck Patent Gmbh | Formulierungen zur herstellung von elektronischen vorrichtungen |
WO2011035836A1 (de) | 2009-09-23 | 2011-03-31 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
DE102009042693A1 (de) | 2009-09-23 | 2011-03-24 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009048791A1 (de) | 2009-10-08 | 2011-04-14 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2011042107A2 (de) | 2009-10-08 | 2011-04-14 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102009049587A1 (de) | 2009-10-16 | 2011-04-21 | Merck Patent Gmbh | Metallkomplexe |
WO2011044988A1 (de) | 2009-10-16 | 2011-04-21 | Merck Patent Gmbh | Metallkomplexe |
WO2011054442A2 (de) | 2009-11-06 | 2011-05-12 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
DE102009053191A1 (de) | 2009-11-06 | 2011-05-12 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
WO2011057701A1 (de) | 2009-11-10 | 2011-05-19 | Merck Patent Gmbh | Organische verbindungen für elektroluminiszenz vorrichtungen |
DE102009052428A1 (de) | 2009-11-10 | 2011-05-12 | Merck Patent Gmbh | Verbindung für elektronische Vorrichtungen |
DE102009053382A1 (de) | 2009-11-14 | 2011-05-19 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
WO2011057706A2 (de) | 2009-11-14 | 2011-05-19 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
DE102009053644B4 (de) | 2009-11-17 | 2019-07-04 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009053644A1 (de) | 2009-11-17 | 2011-05-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2011060859A1 (de) | 2009-11-17 | 2011-05-26 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102009053836A1 (de) | 2009-11-18 | 2011-05-26 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2011060867A1 (de) | 2009-11-18 | 2011-05-26 | Merck Patent Gmbh | Stickstoffhaltige kondensierte heterozyklen für oleds |
DE102009059985A1 (de) | 2009-12-22 | 2011-07-07 | Merck Patent GmbH, 64293 | Polymer mit Aldehydgruppen, Umsetzung sowie Vernetzung dieses Polymers, vernetztes Polymer sowie Elektrolumineszenzvorrichtung enthaltend dieses Polymer |
DE102010004803A1 (de) | 2010-01-16 | 2011-07-21 | Merck Patent GmbH, 64293 | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2011085781A1 (de) | 2010-01-16 | 2011-07-21 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2011088877A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
DE102010005697A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent GmbH, 64293 | Verbindungen für elektronische Vorrichtungen |
WO2011091838A1 (de) | 2010-01-29 | 2011-08-04 | Merck Patent Gmbh | Styrolbasierte copolymere, insbesondere für die anwendung in optoelektronischen bauteilen |
DE102010006377A1 (de) | 2010-01-29 | 2011-08-04 | Merck Patent GmbH, 64293 | Styrolbasierte Copolymere, insbesondere für die Anwendung in optoelektronischen Bauteilen |
DE102010007938A1 (de) | 2010-02-12 | 2011-10-06 | Merck Patent Gmbh | Elektrolumineszierende Polymere, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
WO2011098205A1 (de) | 2010-02-12 | 2011-08-18 | Merck Patent Gmbh | Elektrolumineszierende polymere, verfahren zu ihrer herstellung sowie ihre verwendung |
DE102010009903A1 (de) | 2010-03-02 | 2011-09-08 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
WO2011107186A2 (de) | 2010-03-02 | 2011-09-09 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2011110277A1 (en) | 2010-03-11 | 2011-09-15 | Merck Patent Gmbh | Fibers in therapy and cosmetics |
WO2011116857A1 (en) | 2010-03-23 | 2011-09-29 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
DE102010012738A1 (de) | 2010-03-25 | 2011-09-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2011116865A1 (de) | 2010-03-25 | 2011-09-29 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2011128017A1 (de) | 2010-04-14 | 2011-10-20 | Merck Patent Gmbh | Überbrückte triarylamine und -phosphine als materialien für elektronische vorrichtungen |
DE102010014933A1 (de) | 2010-04-14 | 2011-10-20 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
WO2011137922A1 (de) | 2010-05-03 | 2011-11-10 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
WO2011137951A1 (de) | 2010-05-04 | 2011-11-10 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtungen |
DE102010019306A1 (de) | 2010-05-04 | 2011-11-10 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
DE102010024335A1 (de) | 2010-06-18 | 2011-12-22 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
WO2011157346A1 (de) | 2010-06-18 | 2011-12-22 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
DE102010024542A1 (de) | 2010-06-22 | 2011-12-22 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
WO2011160757A1 (de) | 2010-06-22 | 2011-12-29 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
DE102010024897A1 (de) | 2010-06-24 | 2011-12-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2011160758A1 (de) | 2010-06-24 | 2011-12-29 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102010027316A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metallkomplexe |
WO2012007102A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Polymere materialien für organische elektrolumineszenzvorrichtungen |
WO2012007087A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metallkomplexe |
DE102010027320A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Polymere Materialien für organische Elektrolumineszenzvorrichtungen |
WO2012013310A1 (de) | 2010-07-29 | 2012-02-02 | Merck Patent Gmbh | Polymere enthaltend substituierte benzodithiopheneinheiten, blends enthaltend diese polymere sowie vorrichtungen enthaltend diese polymere oder blends |
DE102010032737A1 (de) | 2010-07-29 | 2012-02-02 | Merck Patent Gmbh | Polymere enthaltend substituierte Benzodithiopheneinheiten, Blends enthaltend diese Polymere sowie Vorrichtungen enthaltend diese Polymere oder Blends |
EP2889320A2 (de) | 2010-08-02 | 2015-07-01 | Merck Patent GmbH | Polymers mit Struktureinheiten, die Elektronen-Transport-Eigenschaften aufweisen |
DE102010033080A1 (de) | 2010-08-02 | 2012-02-02 | Merck Patent Gmbh | Polymere mit Struktureinheiten, die Elektronen-Transport-Eigenschaften aufweisen |
WO2012016627A2 (de) | 2010-08-02 | 2012-02-09 | Merck Patent Gmbh | Polymere mit struktureinheiten, die elektronen-transport-eigenschaften aufweisen |
WO2012016630A1 (de) | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
DE102010033548A1 (de) | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102010045369A1 (de) | 2010-09-14 | 2012-03-15 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2012034626A1 (de) | 2010-09-14 | 2012-03-22 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
EP2787053A1 (de) | 2010-10-14 | 2014-10-08 | Merck Patent GmbH | Polymere Materialien |
WO2012048900A1 (de) | 2010-10-14 | 2012-04-19 | Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung E.V. . | Materialien für organische elektrolumineszenzvorrichtungen |
DE102010048498A1 (de) | 2010-10-14 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
US9653687B2 (en) | 2010-10-14 | 2017-05-16 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2012048778A1 (de) | 2010-10-14 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102010048608A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010048607A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
WO2012048780A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012048781A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Materialien auf basis von triphenylen für organische elektrolumineszenzvorrichtungen |
WO2012084114A1 (de) | 2010-12-23 | 2012-06-28 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
US9136475B2 (en) | 2010-12-24 | 2015-09-15 | Joled Inc. | Organic EL element and method for producing same |
DE102010056151A1 (de) | 2010-12-28 | 2012-06-28 | Merck Patent Gmbh | Materiallen für organische Elektrolumineszenzvorrichtungen |
WO2012089294A1 (de) | 2010-12-28 | 2012-07-05 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2012095143A1 (de) | 2011-01-13 | 2012-07-19 | Merck Patent Gmbh | Verbindungen für organische elektrolumineszenzvorrichtungen |
DE102012000064A1 (de) | 2011-01-21 | 2012-07-26 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
EP2482159A2 (de) | 2011-01-28 | 2012-08-01 | Honeywell International, Inc. | Verfahren und umkonfigurierbare System zur Optimierung der Leistung eines zustandsabhängigen Wartungssystems |
DE102011010841A1 (de) | 2011-02-10 | 2012-08-16 | Merck Patent Gmbh | (1,3)-Dioxan-5-on-Verbindungen |
WO2012107158A1 (de) | 2011-02-10 | 2012-08-16 | Merck Patent Gmbh | 1,3 - dioxan-5-on-verbindungen |
DE102011011539A1 (de) | 2011-02-17 | 2012-08-23 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
WO2012110182A1 (de) | 2011-02-17 | 2012-08-23 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012139693A1 (de) | 2011-04-13 | 2012-10-18 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012139692A1 (de) | 2011-04-13 | 2012-10-18 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2012143079A1 (de) | 2011-04-18 | 2012-10-26 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012149992A1 (de) | 2011-05-04 | 2012-11-08 | Merck Patent Gmbh | Vorrichtung zur aufbewahrung von frischwaren |
WO2012149999A1 (de) | 2011-05-05 | 2012-11-08 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012150001A1 (de) | 2011-05-05 | 2012-11-08 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2012171609A1 (de) | 2011-06-17 | 2012-12-20 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
DE102011104745A1 (de) | 2011-06-17 | 2012-12-20 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
WO2013017189A1 (de) | 2011-07-29 | 2013-02-07 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2013017192A1 (de) | 2011-08-03 | 2013-02-07 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
EP3439065A1 (de) | 2011-08-03 | 2019-02-06 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
DE102011116165A1 (de) | 2011-10-14 | 2013-04-18 | Merck Patent Gmbh | Benzodioxepin-3-on-Verbindungen |
WO2013060418A1 (en) | 2011-10-27 | 2013-05-02 | Merck Patent Gmbh | Materials for electronic devices |
WO2013060411A1 (de) | 2011-10-28 | 2013-05-02 | Merck Patent Gmbh | Hyperverzweigte polymere, verfahren zu deren herstellung sowie deren verwendung in elektronischen vorrichtungen |
WO2013083216A1 (de) | 2011-11-17 | 2013-06-13 | Merck Patent Gmbh | Spiro -dihydroacridinderivate und ihre verwendung als materialien für organische elektrolumineszenzvorrichtungen |
WO2013087142A1 (de) | 2011-12-12 | 2013-06-20 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
DE102012022880A1 (de) | 2011-12-22 | 2013-06-27 | Merck Patent Gmbh | Elektronische Vorrichtungen enthaltend organische Schichten |
EP3101088A1 (de) | 2012-02-14 | 2016-12-07 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
WO2013120577A1 (en) | 2012-02-14 | 2013-08-22 | Merck Patent Gmbh | Spirobifluorene compounds for organic electroluminescent devices |
EP3235892A1 (de) | 2012-02-14 | 2017-10-25 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
WO2013124029A2 (de) | 2012-02-22 | 2013-08-29 | Merck Patent Gmbh | Polymere enthaltend dibenzocycloheptan-struktureinheiten |
WO2013139431A1 (de) | 2012-03-23 | 2013-09-26 | Merck Patent Gmbh | 9,9'-spirobixanthenderivate für elektrolumineszenzvorrichtungen |
WO2013156129A1 (de) | 2012-04-17 | 2013-10-24 | Merck Patent Gmbh | Polymere enthaltend substituierte oligo-triarylamin-einheiten sowie elektrolumineszenzvorrichtungen enthaltend diese polymere |
WO2013156130A1 (de) | 2012-04-17 | 2013-10-24 | Merck Patent Gmbh | Polymere enthaltend substituierte triarylamin-einheiten sowie elektrolumineszenzvorrichtungen enthaltend diese polymere |
WO2013174471A1 (en) | 2012-05-24 | 2013-11-28 | Merck Patent Gmbh | Metal complexes comprising condensed heteroaromatic rings |
WO2013182263A1 (de) | 2012-06-06 | 2013-12-12 | Merck Patent Gmbh | Phenanthrenverbindungen für organische elektronische vorrichtungen |
DE102012011335A1 (de) | 2012-06-06 | 2013-12-12 | Merck Patent Gmbh | Verbindungen für Organische Elekronische Vorrichtungen |
WO2014000860A1 (de) | 2012-06-29 | 2014-01-03 | Merck Patent Gmbh | Polymere enthaltend 2,7-pyren-struktureinheiten |
WO2014008982A1 (de) | 2012-07-13 | 2014-01-16 | Merck Patent Gmbh | Metallkomplexe |
WO2014015938A1 (de) | 2012-07-23 | 2014-01-30 | Merck Patent Gmbh | Derivate von 2-diarylaminofluoren und diese enthaltnde organische elektronische verbindungen |
WO2014015937A1 (de) | 2012-07-23 | 2014-01-30 | Merck Patent Gmbh | Verbindungen und organische elektrolumineszierende vorrichtungen |
DE202013012401U1 (de) | 2012-07-23 | 2016-10-12 | Merck Patent Gmbh | Verbindungen und Organische Elektronische Vorrichtungen |
WO2014015935A2 (de) | 2012-07-23 | 2014-01-30 | Merck Patent Gmbh | Verbindungen und organische elektronische vorrichtungen |
EP3424907A2 (de) | 2012-07-23 | 2019-01-09 | Merck Patent GmbH | Verbindungen und organische elektronische vorrichtungen |
EP3424936A1 (de) | 2012-08-07 | 2019-01-09 | Merck Patent GmbH | Metallkomplexe |
WO2014023377A2 (de) | 2012-08-07 | 2014-02-13 | Merck Patent Gmbh | Metallkomplexe |
WO2014044347A1 (de) | 2012-09-20 | 2014-03-27 | Merck Patent Gmbh | Metallkomplexe |
EP3378857A1 (de) | 2012-11-12 | 2018-09-26 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
WO2014082705A1 (de) | 2012-11-30 | 2014-06-05 | Merck Patent Gmbh | Elektronische vorrichtung |
WO2014101981A1 (en) | 2012-12-28 | 2014-07-03 | Merck Patent Gmbh | Composition comprising polymeric organic semiconducting compounds |
WO2014106522A1 (de) | 2013-01-03 | 2014-07-10 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2014106524A2 (de) | 2013-01-03 | 2014-07-10 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
EP3904361A2 (de) | 2013-10-02 | 2021-11-03 | Merck Patent GmbH | Borenthaltende verbindungen |
EP3693437A1 (de) | 2013-12-06 | 2020-08-12 | Merck Patent GmbH | Verbindungen und organische elektronische vorrichtungen |
EP3345984A1 (de) | 2013-12-06 | 2018-07-11 | Merck Patent GmbH | Verbindungen und organische elektronische vorrichtungen |
WO2015086108A1 (de) | 2013-12-12 | 2015-06-18 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
EP3708634A1 (de) | 2013-12-19 | 2020-09-16 | Merck Patent GmbH | Heterocyclische spiroverbindungen |
WO2015090504A2 (de) | 2013-12-19 | 2015-06-25 | Merck Patent Gmbh | Heterocyclische spiroverbindungen |
WO2016034262A1 (de) | 2014-09-05 | 2016-03-10 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
WO2016074755A1 (de) | 2014-11-11 | 2016-05-19 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2016107663A1 (de) | 2014-12-30 | 2016-07-07 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
US10862038B2 (en) | 2014-12-30 | 2020-12-08 | Merck Patent Gmbh | Compositions comprising at least one polymer and at least one salt, and electroluminescent devices containing said compositions |
WO2016119992A1 (en) | 2015-01-30 | 2016-08-04 | Merck Patent Gmbh | Materials for electronic devices |
WO2016120007A1 (en) | 2015-01-30 | 2016-08-04 | Merck Patent Gmbh | Formulations with a low particle content |
WO2016124304A1 (de) | 2015-02-03 | 2016-08-11 | Merck Patent Gmbh | Metallkomplexe |
WO2016155866A1 (en) | 2015-03-30 | 2016-10-06 | Merck Patent Gmbh | Formulation of an organic functional material comprising a siloxane solvent |
WO2016198144A1 (en) | 2015-06-10 | 2016-12-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP3581633A1 (de) | 2015-06-12 | 2019-12-18 | Merck Patent GmbH | Ester mit nichtaromatischen zyklen als lösungsmittel für oled-formulierungen |
WO2016198141A1 (en) | 2015-06-12 | 2016-12-15 | Merck Patent Gmbh | Esters containing non-aromatic cycles as solvents for oled formulations |
WO2017008883A1 (en) | 2015-07-15 | 2017-01-19 | Merck Patent Gmbh | Composition comprising organic semiconducting compounds |
WO2017012687A1 (en) | 2015-07-22 | 2017-01-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2017012694A1 (en) | 2015-07-23 | 2017-01-26 | Merck Patent Gmbh | Phenyl derivatives substituted with at least two electron acceptors and at least two electron donors for use in organic electronic devices |
EP4236652A2 (de) | 2015-07-29 | 2023-08-30 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
WO2017016630A1 (en) | 2015-07-30 | 2017-02-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP4301110A2 (de) | 2015-07-30 | 2024-01-03 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
WO2017028940A1 (en) | 2015-08-14 | 2017-02-23 | Merck Patent Gmbh | Phenoxazine derivatives for organic electroluminescent devices |
WO2017036572A1 (en) | 2015-08-28 | 2017-03-09 | Merck Patent Gmbh | Formulation of an organic functional material comprising an epoxy group containing solvent |
WO2017036573A1 (en) | 2015-08-28 | 2017-03-09 | Merck Patent Gmbh | Compounds for electronic devices |
WO2017097391A1 (en) | 2015-12-10 | 2017-06-15 | Merck Patent Gmbh | Formulations containing ketones comprising non-aromatic cycles |
WO2017102048A1 (en) | 2015-12-15 | 2017-06-22 | Merck Patent Gmbh | Esters containing aromatic groups as solvents for organic electronic formulations |
EP4084109A1 (de) | 2015-12-15 | 2022-11-02 | Merck Patent GmbH | Ester mit aromatischen gruppen als lösungsmittel für organische elektronische formulierungen |
WO2017102052A1 (en) | 2015-12-16 | 2017-06-22 | Merck Patent Gmbh | Formulations containing a solid solvent |
WO2017102049A1 (en) | 2015-12-16 | 2017-06-22 | Merck Patent Gmbh | Formulations containing a mixture of at least two different solvents |
WO2017133829A1 (de) | 2016-02-05 | 2017-08-10 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2017140404A1 (en) | 2016-02-17 | 2017-08-24 | Merck Patent Gmbh | Formulation of an organic functional material |
DE102016003104A1 (de) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter |
WO2017157783A1 (de) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Behälter umfassend eine formulierung enthaltend mindestens einen organischen halbleiter |
WO2017157983A1 (de) | 2016-03-17 | 2017-09-21 | Merck Patent Gmbh | Verbindungen mit spirobifluoren-strukturen |
WO2017178311A1 (de) | 2016-04-11 | 2017-10-19 | Merck Patent Gmbh | Heterocyclische verbindungen mit dibenzofuran- und/oder dibenzothiophen-strukturen |
WO2017207596A1 (en) | 2016-06-03 | 2017-12-07 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP3978477A2 (de) | 2016-06-03 | 2022-04-06 | Merck Patent GmbH | Materialien für organische elektrolumineszente vorrichtungen |
WO2017216129A1 (en) | 2016-06-16 | 2017-12-21 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2017216128A1 (en) | 2016-06-17 | 2017-12-21 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018001928A1 (en) | 2016-06-28 | 2018-01-04 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018001990A1 (de) | 2016-06-30 | 2018-01-04 | Merck Patent Gmbh | Verfahren zur auftrennung von enantiomerenmischungen von metallkomplexen |
EP3792235A1 (de) | 2016-07-08 | 2021-03-17 | Merck Patent GmbH | Materialien für organische elektrolumineszente vorrichtungen |
WO2018007421A1 (en) | 2016-07-08 | 2018-01-11 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2018011186A1 (de) | 2016-07-14 | 2018-01-18 | Merck Patent Gmbh | Metallkomplexe |
WO2018024719A1 (en) | 2016-08-04 | 2018-02-08 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018050583A1 (de) | 2016-09-14 | 2018-03-22 | Merck Patent Gmbh | Verbindungen mit carbazol-strukturen |
WO2018050584A1 (de) | 2016-09-14 | 2018-03-22 | Merck Patent Gmbh | Verbindungen mit spirobifluoren-strukturen |
WO2018060307A1 (de) | 2016-09-30 | 2018-04-05 | Merck Patent Gmbh | Verbindungen mit diazadibenzofuran- oder diazadibenzothiophen-strukturen |
WO2018060218A1 (de) | 2016-09-30 | 2018-04-05 | Merck Patent Gmbh | Carbazole mit diazadibenzofuran- oder diazadibenzothiophen-strukturen |
EP4255151A2 (de) | 2016-10-10 | 2023-10-04 | Merck Patent GmbH | Spiro[fluoren-9,9'-(thio)xanthen] verbindungen |
EP4113643A1 (de) | 2016-10-10 | 2023-01-04 | Merck Patent GmbH | Elektronische vorrichtung |
WO2018069167A1 (de) | 2016-10-10 | 2018-04-19 | Merck Patent Gmbh | Elektronische vorrichtung |
WO2018077660A1 (en) | 2016-10-31 | 2018-05-03 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018077662A1 (en) | 2016-10-31 | 2018-05-03 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018083053A1 (de) | 2016-11-02 | 2018-05-11 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2018087020A1 (en) | 2016-11-08 | 2018-05-17 | Merck Patent Gmbh | Compounds for electronic devices |
WO2018087346A1 (de) | 2016-11-14 | 2018-05-17 | Merck Patent Gmbh | Verbindungen mit einer akzeptor- und einer donorgruppe |
EP4271163A2 (de) | 2016-11-14 | 2023-11-01 | Merck Patent GmbH | Verbindungen mit einer akzeptor- und einer donorgruppe |
WO2018095839A1 (de) | 2016-11-22 | 2018-05-31 | Merck Patent Gmbh | Verbrückte triarylamine für elektronische vorrichtungen |
WO2018095940A1 (en) | 2016-11-25 | 2018-05-31 | Merck Patent Gmbh | Bisbenzofuran-fused indeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
WO2018095888A1 (en) | 2016-11-25 | 2018-05-31 | Merck Patent Gmbh | Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
WO2018099847A1 (de) | 2016-11-30 | 2018-06-07 | Merck Patent Gmbh | Polymere mit asymmetrischen wiederholungseinheiten |
WO2018099846A1 (de) | 2016-11-30 | 2018-06-07 | Merck Patent Gmbh | Verbindungen mit valerolaktam-strukturen |
EP3978491A1 (de) | 2016-12-05 | 2022-04-06 | Merck Patent GmbH | Stickstoffhaltige heterocyclen zur verwendung in oleds |
WO2018104195A1 (de) | 2016-12-05 | 2018-06-14 | Merck Patent Gmbh | Stickstoffhaltige heterocyclen zur verwendung in oleds |
WO2018104202A1 (en) | 2016-12-06 | 2018-06-14 | Merck Patent Gmbh | Preparation process for an electronic device |
WO2018108760A1 (en) | 2016-12-13 | 2018-06-21 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018114883A1 (de) | 2016-12-22 | 2018-06-28 | Merck Patent Gmbh | Mischungen umfassend mindestens zwei organisch funktionelle verbindungen |
WO2018134392A1 (en) | 2017-01-23 | 2018-07-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2018138039A1 (de) | 2017-01-25 | 2018-08-02 | Merck Patent Gmbh | Carbazolderivate |
WO2018138318A1 (en) | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Method for forming an organic element of an electronic device |
WO2018138319A1 (en) | 2017-01-30 | 2018-08-02 | Merck Patent Gmbh | Method for forming an organic electroluminescence (el) element |
WO2018141706A1 (de) | 2017-02-02 | 2018-08-09 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2018157981A1 (de) | 2017-03-02 | 2018-09-07 | Merck Patent Gmbh | Materialien für organische elektronische vorrichtungen |
WO2018166932A1 (de) | 2017-03-13 | 2018-09-20 | Merck Patent Gmbh | Verbindungen mit arylamin-strukturen |
US10862046B2 (en) | 2017-03-30 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2018178136A1 (en) | 2017-03-31 | 2018-10-04 | Merck Patent Gmbh | Printing method for an organic light emitting diode (oled) |
WO2018189050A1 (en) | 2017-04-10 | 2018-10-18 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018197447A1 (de) | 2017-04-25 | 2018-11-01 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
WO2018202603A1 (en) | 2017-05-03 | 2018-11-08 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2018215318A1 (de) | 2017-05-22 | 2018-11-29 | Merck Patent Gmbh | Hexazyklische heteroaromatische verbindungen für elektronische vorrichtungen |
WO2018234220A1 (de) | 2017-06-21 | 2018-12-27 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2018234346A1 (en) | 2017-06-23 | 2018-12-27 | Merck Patent Gmbh | MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES |
WO2019002190A1 (en) | 2017-06-28 | 2019-01-03 | Merck Patent Gmbh | MATERIALS FOR ELECTRONIC DEVICES |
WO2019007823A1 (en) | 2017-07-03 | 2019-01-10 | Merck Patent Gmbh | LOW-PHENOL IMPURITY FORMULATIONS |
WO2019016184A1 (en) | 2017-07-18 | 2019-01-24 | Merck Patent Gmbh | FORMULATION OF AN ORGANIC FUNCTIONAL MATERIAL |
WO2019020654A1 (en) | 2017-07-28 | 2019-01-31 | Merck Patent Gmbh | SPIROBIFLUORENE DERIVATIVES FOR USE IN ELECTRONIC DEVICES |
WO2019048443A1 (de) | 2017-09-08 | 2019-03-14 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
EP4242286A2 (de) | 2017-11-23 | 2023-09-13 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
WO2019101719A1 (de) | 2017-11-23 | 2019-05-31 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2019115577A1 (en) | 2017-12-15 | 2019-06-20 | Merck Patent Gmbh | Substituted aromatic amines for use in organic electroluminescent devices |
WO2019115573A1 (en) | 2017-12-15 | 2019-06-20 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2019121458A1 (de) | 2017-12-19 | 2019-06-27 | Merck Patent Gmbh | Heterocyclische verbindung zur verwendung in electronischen vorrichtungen |
WO2019121483A1 (en) | 2017-12-20 | 2019-06-27 | Merck Patent Gmbh | Heteroaromatic compounds |
WO2019162483A1 (en) | 2018-02-26 | 2019-08-29 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2019175149A1 (en) | 2018-03-16 | 2019-09-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US10840470B2 (en) | 2018-03-30 | 2020-11-17 | Canon Kabushiki Kaisha | Organic light emitting element, display apparatus, image pickup apparatus, and illumination apparatus |
DE102019108200B4 (de) | 2018-03-30 | 2023-01-05 | Canon Kabushiki Kaisha | Organisches Lichtemissionsbauelement, Anzeigegerät, Bildaufnahmegerät und Beleuchtungsgerät |
WO2019238782A1 (en) | 2018-06-15 | 2019-12-19 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2020064582A1 (de) | 2018-09-24 | 2020-04-02 | Merck Patent Gmbh | Verfahren zur herstellung von granulat |
EP4190880A1 (de) | 2018-09-27 | 2023-06-07 | Merck Patent GmbH | Verbindungen, die in einer organischen elektronischen vorrichtung als aktive verbindungen einsetzbar sind |
WO2020064666A1 (de) | 2018-09-27 | 2020-04-02 | Merck Patent Gmbh | Verbindungen, die in einer organischen elektronischen vorrichtung als aktive verbindungen einsetzbar sind |
WO2020064662A2 (de) | 2018-09-27 | 2020-04-02 | Merck Patent Gmbh | Verfahren zur herstellung von sterisch gehinderten stickstoffhaltigen heteroaromatischen verbindungen |
WO2020094539A1 (de) | 2018-11-05 | 2020-05-14 | Merck Patent Gmbh | In einer organischen elektronischen vorrichtung einsetzbare verbindungen |
WO2020094538A1 (en) | 2018-11-06 | 2020-05-14 | Merck Patent Gmbh | Method for forming an organic element of an electronic device |
WO2020094537A1 (de) | 2018-11-07 | 2020-05-14 | Merck Patent Gmbh | Polymere mit amingruppenhaltigen wiederholungseinheiten |
WO2020099349A1 (de) | 2018-11-14 | 2020-05-22 | Merck Patent Gmbh | Zur herstellung einer organischen elektronischen vorrichtung einsetzbare verbindungen |
WO2020212295A1 (en) | 2019-04-16 | 2020-10-22 | Merck Patent Gmbh | Formulation containing a crosslinkable polymer |
WO2021078710A1 (en) | 2019-10-22 | 2021-04-29 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2021078831A1 (de) | 2019-10-25 | 2021-04-29 | Merck Patent Gmbh | In einer organischen elektronischen vorrichtung einsetzbare verbindungen |
WO2021122538A1 (de) | 2019-12-18 | 2021-06-24 | Merck Patent Gmbh | Aromatische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2021122740A1 (de) | 2019-12-19 | 2021-06-24 | Merck Patent Gmbh | Polycyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2021151922A1 (de) | 2020-01-29 | 2021-08-05 | Merck Patent Gmbh | Benzimidazol-derivate |
WO2021170522A1 (de) | 2020-02-25 | 2021-09-02 | Merck Patent Gmbh | Verwendung von heterocyclischen verbindungen in einer organischen elektronischen vorrichtung |
WO2021175706A1 (de) | 2020-03-02 | 2021-09-10 | Merck Patent Gmbh | Verwendung von sulfonverbindungen in einer organischen elektronischen vorrichtung |
WO2021185829A1 (de) | 2020-03-17 | 2021-09-23 | Merck Patent Gmbh | Heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2021185712A1 (de) | 2020-03-17 | 2021-09-23 | Merck Patent Gmbh | Heteroaromatische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2021191183A1 (de) | 2020-03-26 | 2021-09-30 | Merck Patent Gmbh | Cyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2021204646A1 (de) | 2020-04-06 | 2021-10-14 | Merck Patent Gmbh | Polycyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2021213918A1 (en) | 2020-04-21 | 2021-10-28 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2021254984A1 (de) | 2020-06-18 | 2021-12-23 | Merck Patent Gmbh | Indenoazanaphthaline |
WO2021259824A1 (de) | 2020-06-23 | 2021-12-30 | Merck Patent Gmbh | Verfahren zur herstellung einer mischung |
WO2022002772A1 (de) | 2020-06-29 | 2022-01-06 | Merck Patent Gmbh | Heteroaromatische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2022002771A1 (de) | 2020-06-29 | 2022-01-06 | Merck Patent Gmbh | Heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2022069421A1 (de) | 2020-09-30 | 2022-04-07 | Merck Patent Gmbh | Zur strukturierung von funktionalen schichten organischer elektrolumineszenzvorrichtungen einsetzbare verbindungen |
WO2022069422A1 (de) | 2020-09-30 | 2022-04-07 | Merck Patent Gmbh | Verbindungen zur strukturierung von funktionalen schichten organischer elektrolumineszenzvorrichtungen |
WO2022079068A1 (de) | 2020-10-16 | 2022-04-21 | Merck Patent Gmbh | Heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2022079067A1 (de) | 2020-10-16 | 2022-04-21 | Merck Patent Gmbh | Verbindungen mit heteroatomen für organische elektrolumineszenzvorrichtungen |
WO2022122607A1 (en) | 2020-12-08 | 2022-06-16 | Merck Patent Gmbh | An ink system and a method for inkjet printing |
WO2022129116A1 (de) | 2020-12-18 | 2022-06-23 | Merck Patent Gmbh | Indolo[3.2.1-jk]carbazole-6-carbonitril-derivate als blau fluoreszierende emitter zur verwendung in oleds |
WO2022129113A1 (de) | 2020-12-18 | 2022-06-23 | Merck Patent Gmbh | Stickstoffhaltige heteroaromaten für organische elektrolumineszenzvorrichtungen |
WO2022129114A1 (de) | 2020-12-18 | 2022-06-23 | Merck Patent Gmbh | Stickstoffhaltige verbindungen für organische elektrolumineszenzvorrichtungen |
WO2022223675A1 (en) | 2021-04-23 | 2022-10-27 | Merck Patent Gmbh | Formulation of an organic functional material |
WO2022229234A1 (de) | 2021-04-30 | 2022-11-03 | Merck Patent Gmbh | Stickstoffhaltige, heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2022243403A1 (de) | 2021-05-21 | 2022-11-24 | Merck Patent Gmbh | Verfahren zur kontinuierlichen aufreinigung von mindestens einem funktionalen material und vorrichtung zur kontinuierlichen aufreinigung von mindestens einem funktionalen material |
WO2023041454A1 (de) | 2021-09-14 | 2023-03-23 | Merck Patent Gmbh | Borhaltige, heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2023057327A1 (en) | 2021-10-05 | 2023-04-13 | Merck Patent Gmbh | Method for forming an organic element of an electronic device |
WO2023072799A1 (de) | 2021-10-27 | 2023-05-04 | Merck Patent Gmbh | Bor- und stickstoffhaltige, heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2023099543A1 (en) | 2021-11-30 | 2023-06-08 | Merck Patent Gmbh | Compounds having fluorene structures |
WO2023161167A1 (de) | 2022-02-23 | 2023-08-31 | Merck Patent Gmbh | Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2023161168A1 (de) | 2022-02-23 | 2023-08-31 | Merck Patent Gmbh | Aromatische heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2023213759A1 (de) | 2022-05-04 | 2023-11-09 | Merck Patent Gmbh | Polymere enthaltend speziell substituierte triarylamin-einheiten sowie elektrolumineszenzvorrichtungen enthaltend diese polymere |
WO2023213837A1 (de) | 2022-05-06 | 2023-11-09 | Merck Patent Gmbh | Cyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2023247338A1 (de) | 2022-06-20 | 2023-12-28 | Merck Patent Gmbh | Organische heterocyclen für photoelektrische vorrichtungen |
WO2023247345A1 (de) | 2022-06-20 | 2023-12-28 | Merck Patent Gmbh | Heterocyclen für photoelektrische vorrichtungen |
WO2024061942A1 (de) | 2022-09-22 | 2024-03-28 | Merck Patent Gmbh | Stickstoffenthaltende verbindungen für organische elektrolumineszenzvorrichtungen |
WO2024061948A1 (de) | 2022-09-22 | 2024-03-28 | Merck Patent Gmbh | Stickstoffenthaltende heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2024094592A2 (de) | 2022-11-01 | 2024-05-10 | Merck Patent Gmbh | Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2024115426A1 (de) | 2022-12-01 | 2024-06-06 | Merck Patent Gmbh | Polymere enthaltend spirotruxenderivate als wiederholungseinheit sowie elektrolumineszenzvorrichtungen enthaltend diese polymere |
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Publication number | Publication date |
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EP1675930B1 (de) | 2018-05-30 |
US7659540B2 (en) | 2010-02-09 |
EP2366752A2 (de) | 2011-09-21 |
KR101215160B1 (ko) | 2012-12-24 |
EP2366752B1 (de) | 2016-07-20 |
EP1675930A1 (de) | 2006-07-05 |
KR20060090833A (ko) | 2006-08-16 |
US20070080343A1 (en) | 2007-04-12 |
US20100102305A1 (en) | 2010-04-29 |
EP2366752A3 (de) | 2012-05-30 |
US8173276B2 (en) | 2012-05-08 |
JP2007517079A (ja) | 2007-06-28 |
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