The Metal Is Bonded Directly To Carbon, Which Carbon Is A Ring Carbon Of The Five-membered Hetero Ring Or Which Carbon Is Attached Directly Or Indirectly To The Five-membered Hetero Ring By Nonionic Bonding Patents (Class 548/103)
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Patent number: 11999754Abstract: The invention relates to a ruthenium complex of formula (1), (1) wherein all variables have a meaning as defined in the specification to be used as a (pre)catalyst in the olefin metathesis reaction, ring metathesis reaction (RCM), homometathesis (self-CM), cross-metathesis including ethanolysis (CM).Type: GrantFiled: April 16, 2019Date of Patent: June 4, 2024Assignee: APEIRON SYNTHESIS S.A.Inventors: Rafal Gawin, Patryk Krajczy, Anna Gawin, Krzysztof Skowerski
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Patent number: 11858949Abstract: Provided are an organometallic compound represented by Formula 1, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound.Type: GrantFiled: June 11, 2020Date of Patent: January 2, 2024Assignee: SAMSUNG ELECTRONICS CO., LTD.Inventors: Hyejin Bae, Minsik Min, Eunsuk Kwon, Sangmo Kim, Hasup Lee, Soonok Jeon, Jongsoo Kim, Sungho Nam, Hyeonho Choi
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Patent number: 11545691Abstract: A redox flow battery includes a cathode, an anode, a charge-carrying electrolyte, and an (a) oxidized and a (b) reduced form of an active material. The active material has the following formula: (D)-(L)-(A)-[(L)-(A)]V-DZ(F1) or (D)-(L)-(A)-(L-D)X (F2). In these formulae, each D is covalently bonded to an L, each L is covalently bonded to an A, x is a number from 0 to 5, v is a number from 0 to 5 and z is 0 or 1. D is an electron donor compound, L is a linker, and A is an electron acceptor compound. Each of D, L, and A has a particular structure.Type: GrantFiled: July 20, 2018Date of Patent: January 3, 2023Assignee: Board of Trustees of Michigan State UniversityInventor: Thomas F. Guarr
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Patent number: 11404650Abstract: Organic light emitting materials and devices comprising phosphorescent metal complexes comprising ligands comprising aryl or heteroaryl groups substituted at both ortho positions are described. An organic light emitting device, comprising: an anode, a hole transport layer; an organic emissive layer comprising an emissive layer host and an emissive dopant; an electron impeding layer; and electron transport layer; and a cathode disposed, in that order, over a substrate.Type: GrantFiled: July 1, 2019Date of Patent: August 2, 2022Assignee: UNIVERSAL DISPLAY CORPORATIONInventors: Chun Lin, Peter B. MacKenzie, Robert W. Walters, Jui-Yi Tsai, Cory S. Brown, Jun Deng
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Patent number: 11033889Abstract: The present invention provides Acyclic diaminocarbene complex of formula (I): Wherein, M is palladium; X is monoanionic ligand selected from Cl, Br or I; Where R1 is different from R2; R1 is selected from the group consisting of alkyl or aryl, each of which have 4 to 20 carbon atoms, and may optionally contain one or more heteroatoms; R2 is selected from the group consisting of alkyl, or aryl each of which have 4 to 20 carbon atoms, and may optionally contain one or more heteroatoms. The said palladium diamino carbine complex of the present invention are particularly useful as catalyst from Hiyama cross-coupling reaction.Type: GrantFiled: October 23, 2018Date of Patent: June 15, 2021Assignee: INDIAN INSTITUTE OF TECHNOLOGY BOMBAYInventors: Chandan Singh, Prasenjit Ghosh
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Patent number: 10930866Abstract: A method of making an osmium(II) complex having Formula I, L1-Os-L2, wherein L1 and L2 are independently a biscarbene tridentate ligand, wherein L1 and L2 can be same or different is disclosed. The method includes (a) reacting a precursor of ligand L1 with an osmium precursor to form an intermediate product, wherein the osmium precursor having the formula OsHx(PR3)y, wherein x is an integer from 2 to 6 and y is an integer from 2 to 5, and R is selected from the group consisting of aryl, alkyl and cycloalkyl; and (b) reacting a precursor of ligand L2 with said intermediate product.Type: GrantFiled: February 7, 2020Date of Patent: February 23, 2021Assignee: UNIVERSAL DISPLAY CORPORATIONInventors: Chuanjun Xia, Jui-Yi Tsai, Beatriz Eguillor Armendariz, Miguel A. Esteruelas Rodrigo, Roberto Gomez Alabau, Montserrat Olivan Esco, Enrique Onate Rodriguez
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Patent number: 10457864Abstract: Novel Iridium complexes having three different bidentate ligands useful for phosphorescent emitters in OLEDs are disclosed. At least one of the three different bidentate ligands is a carbene ligand.Type: GrantFiled: January 10, 2018Date of Patent: October 29, 2019Assignee: Universal Display CorporationInventors: Jui-Yi Tsai, Chuanjun Xia, Chun Lin, Adrian U. Palacios, Enrique Oñate, Miguel A. Esteruelas, Pierre-Luc T. Boudreault, Sonia Bajo, Montserrat Oliván
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Patent number: 10319919Abstract: An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, wherein the organic layer comprises a compound represented by Formula 1. An organic light-emitting device including the compound may have high efficiency, low voltage, high luminance, and a long lifespan.Type: GrantFiled: June 8, 2016Date of Patent: June 11, 2019Assignee: Samsung Display Co., Ltd.Inventors: Eunyoung Lee, Youngkook Kim, Junha Park, Munki Sim, Hyoyoung Lee, Eunjae Jeong, Seokhwan Hwang
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Patent number: 10017531Abstract: The present disclosure is in relation to the field of nanotechnology and cancer therapeutics. In particular, the present disclosure relates to carbene compounds, particularly platinum containing carbenes and corresponding nanoparticles thereof. The disclosure further relates to synthesis of said platinum containing carbenes, nanoparticles and compositions comprising said platinum containing carbenes/nanoparticles. The disclosure also relates to methods of managing cancer by employing aforesaid platinum based compounds, nanoparticles and compositions.Type: GrantFiled: June 13, 2014Date of Patent: July 10, 2018Assignee: INVICTUS ONCOLOGY PVT. LTD.Inventors: Arindam Sarkar, Swadhin Kumar Mandal
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Patent number: 9938253Abstract: The present application provides, among other things, compounds and methods for metathesis reactions. In some embodiments, provided compounds promote highly efficient and highly Z-selective metathesis. In some embodiments, provided compounds and methods are particularly useful for producing allyl alcohols. In some embodiments, provided compounds have the structure of formula I. In some embodiments, provided compounds comprise ruthenium, and a ligand bonded to ruthenium through a sulfur atom.Type: GrantFiled: June 12, 2014Date of Patent: April 10, 2018Assignee: Trustees of Boston CollegeInventors: Amir H. Hoveyda, R. Kashif M. Khan, Sebastian Torker, Ming Joo Koh
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Patent number: 9773985Abstract: A compound according to Formula I, as well as, devices and formulations containing the compound as described. The compound has the general formula wherein n=1 or 2; wherein X1-X2 is a bidentate ligand having the formula: wherein each of R1, R2, R3, R4 and R5 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein each of R3, R4 and R5 can also be selected from two adjacent substituents joined to form into a ring; wherein each of Z1, Z2, Z3, Z4, Z6, Z7, Z8 is independently selected from C, CH or N; wherein ring A is connected to ring B through N—C bond; and wherein Y1-Y2 is a different bidentate ligand other than X1-X2.Type: GrantFiled: March 13, 2013Date of Patent: September 26, 2017Assignee: UNIVERSAL DISPLAY CORPORATIONInventors: Lichang Zeng, Edward Barron, Bin Ma, Chuanjun Xia
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Patent number: 9637510Abstract: A method for preparing a ruthenium carbene complex precursor includes reacting a ruthenium refinery salt with a hydrogen halide to form a ruthenium intermediate, and reacting the ruthenium intermediate with an L-type ligand to form the ruthenium carbene complex precursor. A method for preparing a ruthenium vinylcarbene complex includes converting a ruthenium carbene complex precursor into a ruthenium hydrido halide complex, and reacting the ruthenium hydrido halide complex with a propargyl halide to form the ruthenium vinylcarbene complex. A method for preparing a ruthenium carbene complex includes converting a ruthenium carbene complex precursor into a ruthenium carbene complex having a structure (PR1R2R3)2Cl2Ru?CH—R4, wherein R1, R2, R3, and R4 are alike or different, and wherein covalent bonds may optionally exist between two or more of R1, R2, and R3 and/or two of R1, R2, and R3 taken together may optionally form a ring with phosphorous.Type: GrantFiled: January 30, 2015Date of Patent: May 2, 2017Assignee: Elevance Renewable Sciences, Inc.Inventors: Linda A. Kunz, Steven A. Cohen
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Patent number: 9562116Abstract: The invention relates to a method for preparation of ruthenium-based carbene catalysts with a chelating alkylidene ligand (“Hoveyda-type catalysts”) by reacting a penta coordinated ruthenium (II)-alkylidene complex of the type (L) (Py)X1X2Ru(alkylidene) with a suitable olefin derivative in a cross metathesis reaction. The method delivers high yields and is conducted preferably in aromatic hydrocarbon solvents. The use of phosphine-containing Ru carbene complexes as starting materials can be avoided. Catalyst products with high purity, particularly with low Cu content, can be obtained.Type: GrantFiled: August 28, 2014Date of Patent: February 7, 2017Assignees: UMICORE AG & CO. KG, GRAZ UNIVERSITY OF TECHNOLOGYInventors: Roland Winde, Angelino Doppiu, Eileen Woerner, Andreas Rivas-Nass, Ralf Karch, Christian Slugovc, Christina Schinagl
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Patent number: 9457347Abstract: The present invention refers to novel ruthenium- and osmium-based catalysts for olefin metathesis reactions, particularly to catalysts having stereoselective properties. Z-selectivity is obtained by utilizing two mono-anionic ligands of very different steric requirement. In olefin metathesis reactions these catalysts selectively provide the Z-isomer of disubstituted olefinic products.Type: GrantFiled: May 2, 2014Date of Patent: October 4, 2016Assignee: Bergen Teknologioverforing ASInventors: Vidar R. Jensen, Giovanni Occhipinti, Frederik R. Hansen
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Patent number: 9328132Abstract: The invention is related to the metal complexes of the general formula (1). The invention is related also to the use of metal complexes of the formula 1 as (pre)catalysts for the olefin metathesis reactions, as well as to the process for carrying out the olefin metathesis reaction.Type: GrantFiled: July 26, 2013Date of Patent: May 3, 2016Assignee: APEIRON SYNTHESIS S.A.Inventors: Krzysztof Skowerski, Michal Bieniek
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Patent number: 9309344Abstract: The present invention relates to a process for preparing polymers by means of ring-opening metathetic polymerization, consisting of the following steps: a) providing a reaction mixture consisting of a cycloalkene or a cycloalkene mixture, b) adding a ruthenium compound of the general formula RuX1X2L1aL2b (I) where a=0 or 1, b=1 or 2, such that a+b=2; X1, X2=independently selected anionic ligands; L1=uncharged ?-binding ligand; L2=N-heterocyclic carbene of the formula IIa, IIb or IIc; c) adding a chain transfer agent in a molar ratio in the range from 1:5 to 1:1000 based on the cycloalkene or the sum total of the cycloalkenes in the cycloalkene mixture, d) converting at a temperature within a range from 0° C. to 250° C.Type: GrantFiled: April 10, 2015Date of Patent: April 12, 2016Assignee: Evonik Degussa GmbHInventors: Renat Kadyrov, Christa Dumrath, Matthias Beller, Andreas Dumrath, Helfried Neumann, Stephanie Klein
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Patent number: 9139599Abstract: Embodiments of the present disclosure provide for chemical assemblies, multidimensional metal-organic frameworks (MOFs), supermolecular building layers (SBLs), inorganic molecular building blocks (MBBs), organic MBBs (designed ligands), methods of making each, and methods of using each, and the like. In an embodiment, the composition can be used in catalysis, separations, gas storage, and drug delivery.Type: GrantFiled: June 6, 2013Date of Patent: September 22, 2015Assignees: University of South Florida, King Abdullah University of Science and TechnologyInventors: Mohamed Eddaoudi, Jarrod F. Eubank
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Patent number: 9115095Abstract: Provided herein are ruthenium complexes of Formula I, and processes of preparation thereof. Also provided are methods of their use as a metathesis catalyst.Type: GrantFiled: June 6, 2014Date of Patent: August 25, 2015Assignee: Idenix Pharmaceuticals, Inc.Inventors: Christophe Claude Parsy, Francois-Rene Alexandre, Florence Marie-Emilie Bonnaterre, Dominique Surleraux
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Patent number: 9093651Abstract: In an aspect, a composition including an acrylate monomer, and aromatic aryl amine compound, an organic light emitting display apparatus including the composition and a method of manufacturing an organic light emitting display apparatus including the composition are provided.Type: GrantFiled: July 14, 2014Date of Patent: July 28, 2015Assignee: Samsung Display Co., Ltd.Inventors: Byoung-Duk Lee, Yong-Tack Kim, Jong-Woo Kim, Min-Ho Oh, So-Young Lee, Jin-Hwan Jeon, Yun-Ah Chung, Yoon-Hyeung Cho, Yong-Chan Ju
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Patent number: 9082989Abstract: Synthesis of platinum(II) di(2-pyrazolyl)benzene chloride and analogs includes forming a 1,3-di-substituted benzene including two aromatic five-membered heterocycles, and reacting the 1,3-di-substituted benzene with an acidic platinum-containing solution to form a luminescent platinum(II) complex. The luminescent platinum(II) complex is capable of emitting blue and white light and can be used as an emitter in a light emitting device.Type: GrantFiled: September 29, 2014Date of Patent: July 14, 2015Assignee: Arizona Board of Regents for and on behalf of Arizona State UnivesityInventors: Jian Li, Zixing Wang
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Patent number: 9074028Abstract: The present invention provides new ruthenium complexes of Formula (1), which contain a chelate ring created by a halogen atom X. The invention concerns also a method for the preparation of the new ruthenium complexes and their application in metathesis reactions.Type: GrantFiled: June 4, 2012Date of Patent: July 7, 2015Assignee: UMICORE AG & CO. KGInventors: Karol Leslaw Grela, Michal Barbasiewicz, Michal Michalak
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Patent number: 9076974Abstract: A platinum (II) complex of general formula (II), in which Ar1 is a 1,2-diazole ring, Ar2 is a pyridine ring, and Ar3 is a phenyl ring. Ar1, Ar2, and Ar3 together form a tridentate ligand coordinated to the platinum through atoms X, Y, and Z, respectively, and X, Y, and Z are independently carbon or nitrogen. V represents O, S, N, C, P, or Si, and W is an anion. In some cases, Ar3 is an anion and Ar1 and Ar2 are neutral; in other cases, Ar1 and Ar3 are neutral and Ar2 is an anion. The complexes emit in the UV to near IR range and are useful as emitters for organic light emitting devices.Type: GrantFiled: March 10, 2014Date of Patent: July 7, 2015Assignee: Arizona Board of Regents for and on behalf of Arizona State UniversityInventors: Jian Li, Zixing Wang, Eric Turner
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Patent number: 9040513Abstract: Described is a process for preparing platinum-carbene complexes.Type: GrantFiled: December 22, 2011Date of Patent: May 26, 2015Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, UNIVRSITE DE STRASBOURGInventors: Stéphane Bellemin-Laponnaz, Gilles Guichard, Edith Chardon
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Publication number: 20150139901Abstract: The present invention concerns radioactive rhodium complexes, their preparation methods, and their use for the radiolabelling of biomolecules, especially monoclonal antibodies.Type: ApplicationFiled: May 14, 2013Publication date: May 21, 2015Applicants: Institut National de la Sante et de la Recherche (INSERM), Chu Nantes, Universite de Nantes, Centre National de la Recherche Scientifique (C.N.R.S.), Universite d' AngersInventors: Alain Faivre-Chauvet, Holisoa Rajaerison, Jean-Francois Gestin
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Publication number: 20150129840Abstract: A novel emitter compound having the formula Os(L1)(L2)(L3) and a novel method of making such compounds are disclosed. In the formula Os(L1)(L2)(L3), each of L1, L2, and L3 is independently a bidentate ligand. The method includes (a) reacting a precursor of ligand L1 with an osmium precursor to form a first intermediate product that has the ligand L1 coordinated to the osmium, wherein the osmium precursor has the formula OsHx(PR3)y, wherein x is an integer from 2 to 6 and y is an integer from 2 to 5, and R is selected from the group consisting of aryl, alkyl and cycloalkyl; (b) reacting the first intermediate product with a reducing agent to form a Os(II) second intermediate product; (c) reacting the second intermediate product with a coordinating solvent to form a third intermediate product; and (d) reacting a mixture of ligands L2 and L3 with said third intermediate product.Type: ApplicationFiled: November 8, 2013Publication date: May 14, 2015Applicant: Universal Display CorporationInventors: Jui-Yi Tsai, Chuanjun Xia, Miguel A. Esteruelas, Enrique Oñate Rodriguez, Tamara Bolano, Adrian U. Palacios
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Patent number: 9028975Abstract: Disclosed is a method of producing an organic light emitting device, an organic light emitting device produced by using the method, and an apparatus used in the method. The method includes preparing a first electrode, forming one or more organic material layers on the first electrode, and forming a second electrode on the organic material layers, wherein the method includes changing functions of predetermined pattern regions of one or more layers of the organic material layers or the electrodes.Type: GrantFiled: May 3, 2007Date of Patent: May 12, 2015Assignee: LG Chem, Ltd.Inventors: Min-Soo Kang, Yun-Hye Hahm
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Patent number: 9029541Abstract: A novel binuclear metal complex containing a biimidazole as a bridging ligand. The binuclear metal complex can be used as a material for an organic electroluminescence element.Type: GrantFiled: December 2, 2011Date of Patent: May 12, 2015Assignee: Ube Industries, Ltd.Inventors: Osamu Fujimura, Kenji Fukunaga, Takafumi Iwasa, Yasuhiro Tanaka, Harunori Fujita, Tadashi Murakami, Takashi Honma, Toshikazu Machida, Natsuko Kashihara
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Patent number: 9029804Abstract: We report the synthesis and characterization of four novel CCC-NHC pincer platinum(II) and palladium(II) complexes, which adopt a distorted square planar configuration. These complexes emit bright blue light in the solid state under UV irradiation with emissions that are stable in ambient atmosphere (O2 and H2O) for extended periods. We also report the synthesis and characterization of CCC-NHC pincer ligand nickel complexes, and solid state fluorescence spectra have been collected for two of the complexes reported. X-ray structural analysis of a representative compound exhibits a distorted square planar geometry. Finally, we report the synthesis and characterization of CCC-NHC pincer ligand complexes for abnormal carbenes, triazole, and BIA.Type: GrantFiled: October 19, 2010Date of Patent: May 12, 2015Assignee: University of MississippiInventors: Thedford Keith Hollis, Xiaofei Zhang
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Publication number: 20150126744Abstract: This disclosure relates to new metal complexes, such as compounds of Formula 1, and their application in olefin or alkyne metathesis and to methods of carrying out olefin metathesis reactions.Type: ApplicationFiled: December 12, 2014Publication date: May 7, 2015Inventors: Krzysztof Skowerski, Michal Bieniek
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Patent number: 9024034Abstract: This invention relates to a metathesis catalyst compound comprising an asymmetrically substituted N-heterocyclic carbene (NHC) metathesis catalyst and a process to make linear alpha-olefins comprising contacting a feed material and an optional alkene (such as ethylene) with said catalyst, where the feed material is a triacylglyceride, fatty acid, fatty acid alkyl ester, and/or fatty acid ester, typically derived from biodiesel.Type: GrantFiled: November 3, 2010Date of Patent: May 5, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Matthew W. Holtcamp, Matthew S. Bedoya, Catherine A. Faler, Caol P. Huff, John R. Hagadorn, Ravindra Ganesh
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Patent number: 9024308Abstract: Use of transition metal complexes of the formula (I) in organic light-emitting diodes where: M1 is a metal atom; carbene is a carbene ligand; L is a monoanionic or dianionic ligand; K is an uncharged monodentate or bidentate ligand selected from the group consisting of phosphines; CO; pyridines; nitriles and conjugated dienes which form a ? complex with M1; n is the number of carbene ligands and is at least 1; m is the number of ligands L, where m can be 0 or ?1; o is the number of ligands K, where o can be 0 or ?1; where the sum n+m+o is dependent on the oxidation state and coordination number of the metal atom and on the denticity of the ligands carbene, L and K and also on the charge on the ligands carbene and L, with the proviso that n is at least 1, and also an OLED comprising these transition metal complexes, a light-emitting layer comprising these transition metal complexes, OLEDs comprising this light-emitting layer, devices comprising an OLED according to the present invention, and specific tType: GrantFiled: November 13, 2014Date of Patent: May 5, 2015Assignee: BASF SEInventors: Markus Bold, Christian Lennartz, Martina Egen, Hans-Werner Schmidt, Mukundan Thelakkat, Markus Baete, Christian Neuber, Wolfgang Kowalsky, Christian Schildknecht, Hans-Hermann Johannes
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Publication number: 20150115250Abstract: Fluorine substituted metal complexes as efficient phosphorescent emitters is disclosed. The fluorine substitution is at para position of a phenyl group.Type: ApplicationFiled: September 10, 2014Publication date: April 30, 2015Inventors: Bin MA, Chuanjun XIA, Chun LIN
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Patent number: 9018387Abstract: Metal imidazolate complexes are described where imidazoles ligands functionalized with bulky groups and their anionic counterpart, i.e., imidazolates are described. Compounds comprising one or more such polyalkylated imidazolate anions coordinated to a metal or more than one metal, selected from the group consisting of alkali metals, transition metals, lanthanide metals, actinide metals, main group metals, including the chalcogenides, are contemplated. Alternatively, multiple different imidazole anions, in addition to other different anions, can be coordinated to metals to make new complexes. The synthesis of novel compounds and their use to form thin metal containing films is also contemplated.Type: GrantFiled: June 3, 2011Date of Patent: April 28, 2015Assignee: Air Products and Chemicals, Inc.Inventors: John Anthony Thomas Norman, Melanie K. Perez, Xinjian Lei, Daniel P. Spence, Sergei Vladimirovich Ivanov, Wade Hampton Bailey, III
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Patent number: 9018199Abstract: The present invention relates to organometallic compounds useful in the treatment of metastasis. The organometallic compounds comprise a ligand that is covalently bound to a bioactive compound, which is an inhibitor of a resistance pathway or a derivative thereof. Preferably, the organometallic compounds are half-sandwich (“piano-stool”) compounds. The compounds of the present invention offer a high variability with respect to the bioactive compound and to the nature of the ligand bound to a central transition metal.Type: GrantFiled: May 9, 2007Date of Patent: April 28, 2015Assignee: Ecole Polytechnique Federale de Lausanne (EPFL)Inventors: Paul Joseph Dyson, Wee Han Ang
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Publication number: 20150108451Abstract: A compound having a structure according to formula (I) is disclosed. In formula (I), Cu is a monovalent copper atom; *C is a carbene carbon; X1 and X2 are selected from alkyl, cycloalkyl, alkoxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, arylalkyl, aryloxy, aryl, heteroalkyl, heteroaryl, and combinations thereof; X1 and X2 are independently bonded to *C by an atom selected from C, N, O, S, and P; X1 and X2 are optionally joined to form a ring; and Y is selected halide, alkyl, cycloalkyl, alkoxy, amino, phosphine, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroalkynyl, arylalkyl, aryloxy, aryl, heteroalkyl, heteroaryl, and combinations thereof. A formulation containing compound having a structure according to formula (I), and a device with an organic layer comprising disposed between an anode and a cathode, that includes a compound having a structure according to formula (I) are also described.Type: ApplicationFiled: September 5, 2014Publication date: April 23, 2015Inventors: Mark E. Thompson, Peter I. Djurovich, Valentina Krylova
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Patent number: 9012036Abstract: To provide a novel organometallic complex, and light emitting elements, light emitting devices, and electronic devices which include the organometallic complex. In addition, to provide a composition in which the organometallic complex is dissolved and to provide a method for manufacturing light emitting elements using the composition. An organometallic complex has high solubility in a solvent. In the organometallic complex, the ligand including a pyrazine skeleton is bound to an atom belonging to Group 9 (Co, Rh, or Ir) or an atom belonging to Group 10 (Ni, Pd, or Pt). In addition, the light emission efficiency is high. Therefore, the organometallic complex is preferably used for manufacturing a light emitting element.Type: GrantFiled: May 14, 2008Date of Patent: April 21, 2015Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Hideko Inoue, Satoko Shitagaki, Satoshi Seo
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Patent number: 9005773Abstract: A novel substance exhibiting phosphorescence is provided. The novel substance is an organometallic complex represented by General Formula (G1). In General Formula (G1), R1 represents a haloalkyl group having 1 to 9 carbon atoms which may have a substituent. In addition, R2 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent, and an aryl group having 6 to 12 carbon atoms which may have a substituent. Further, Ar represents an arylene group having 6 to 13 carbon atoms which may have a substituent. M represents either a Group 9 element or a Group 10 element.Type: GrantFiled: March 10, 2011Date of Patent: April 14, 2015Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Hideko Inoue, Tomoka Nakagawa, Nobuharu Ohsawa, Satoshi Seo
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Patent number: 8999520Abstract: An organometallic complex having a structure represented by the following general formula (G1) is provided. (In the formula, A represents an aromatic hydrocarbon group having 6 to 25 carbon atoms. Further, Z represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. In addition, Ar1 represents an aryl group having 6 to 25 carbon atoms. R1 represents any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. Further, M is a central metal and represents an element belonging to Group 9 or Group 10.Type: GrantFiled: March 20, 2007Date of Patent: April 7, 2015Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Hideko Inoue, Satoshi Seo, Nobuharu Ohsawa
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Publication number: 20150093890Abstract: A metal precursor and a method comprising decomposing a metal precursor on an integrated circuit device; and forming a metal from the metal precursor, wherein the metal precursor is selected from the group consisting of (i) a Co2(CO)6(R1C?CR2), wherein R1 and R2 are individually selected from a straight or branched monovalent hydrocarbon group have one to six carbon atoms that may be interrupted and substituted; (ii) a mononuclear cobalt carbonyl nitrosyl; (iii) a cobalt carbonyl bonded to one of a boron, indium, germanium and tin moiety; (iv) a cobalt carbonyl bonded to a mononuclear or binuclear allyl; and (v) a cobalt (II) complex comprising nitrogen-based supporting ligands.Type: ApplicationFiled: September 27, 2013Publication date: April 2, 2015Inventors: James M. Blackwell, Scott B. Clendenning, John J. Plombon, Patricio E. Romero
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Patent number: 8986856Abstract: The present invention provides a novel iridium complex and an organic light-emitting element including the same. The novel iridium complex includes phenylpyrazole as a ligand and has a basic skeleton in which a pyrimidine ring is bonded to a phenyl ring.Type: GrantFiled: November 26, 2010Date of Patent: March 24, 2015Assignee: Canon Kabushiki KaishaInventors: Chiaki Nishiura, Shigemoto Abe, Masashi Hashimoto, Hiroya Nitta
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Patent number: 8987451Abstract: A single-step method of making tetradentate platinum complexes is disclosed. The method advantageously allows the formation of a platinum complex in a single step, even with sterically hindered ligands, without the use of highly reactive intermediates. The compounds made by the disclosed method are useful in OLED applications.Type: GrantFiled: December 20, 2012Date of Patent: March 24, 2015Assignee: Universal Display CorporationInventors: Jui-Yi Tsai, Gregg Kottas, Walter Yeager
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Publication number: 20150076470Abstract: The present invention relates to phosphorescent (triplet-emitting) organometallic materials. The phosphorescent materials of the present invention comprise Ir(III)cyclometallated alkynyl complexes for use as triplet light-emitting materials. The Ir(III)cyclometallated alkynyl complexes comprise at least one cyclometallating ligand and at least one alkynyl ligand bonded to the iridium. Also provided is an organic light emitting device comprising an anode, a cathode and an emissive layer between the anode and the cathode, wherein the emissive layer comprises a Ir(III)cyclometallated alkynyl complex as a triplet emitting material.Type: ApplicationFiled: August 4, 2014Publication date: March 19, 2015Inventors: Mark E. Thompson, Alberto Bossi, Peter ivan Djurovich
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Publication number: 20150076466Abstract: There is provided a compound having Formula I In the formula: Ar is a substituted or unsubstituted aryl group; and R1-R8 are the same or different and are H, D, alkyl, aryl, silyl, deuterated alkyl, deuterated aryl, or deuterated silyl.Type: ApplicationFiled: April 19, 2013Publication date: March 19, 2015Inventor: Kyung-Ho Park
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Publication number: 20150076454Abstract: Bis(tridentate) osmium(II) complexes containing phosphite groups useful as phosphorescent emitters are disclosed. The disclosed osmium(II) complexes have higher oxidation potential then previously known osmium(II) complexes. An organic light emitting device having an organic layer that includes the disclosed osmium(II) complex is also disclosed.Type: ApplicationFiled: September 13, 2013Publication date: March 19, 2015Applicant: Universal Display CorporationInventor: Jui-Yi Tsai
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Publication number: 20150080581Abstract: Improved catalysts useful in alkyne or olefin metathesis are made by bringing into contact a multi-coordinated metal complex comprising a multidentate Schiff base ligand, and one or more other ligands, with a selected activating compound under conditions such that at least partial cleavage of a bond between the metal and the multidentate Schiff base ligand of said metal complex occurs.Type: ApplicationFiled: November 25, 2014Publication date: March 19, 2015Applicant: RIMTEC CORPORATIONInventors: David SCHAUBROECK, Stijn MONSAERT, Nele LEDOUX, Francis Walter Cornelius VERPOORT, Renata A. DROZDZAK
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Patent number: 8980440Abstract: This invention pertains to light emitting materials comprising novel ortho-metalated transition metal complexes [C^N]2M(T)(L), comprising chelate dialkylamino-substituted C^N ligands, monodentate neutral ligand (L) having sp2 hybridized N atom and a monodentate anionic ligand (T) chosen among CN?, CNO?, CNS?. It has been surprisingly found that when the metal has bound thereto in addition to substituted orthometalated ligands, both an anion chosen among cyanide, thiocyanate, cyanate, possessing strong C donor and ? acceptor properties, and a monodentate neutral ligand L, as above defined, said ligands advantageously participate in the emission process, significantly shifting emission towards higher energies (blue-shift) and enabling appreciable improvement of the emission efficiency of complexes [C^N]2M(T)(L). Still objects of the invention are the use of said light emitting materials and organic light emitting device comprising said light emitting material.Type: GrantFiled: April 3, 2007Date of Patent: March 17, 2015Assignee: Solvay (Societe Anonyme)Inventors: Mohammad Khaja Nazeeruddin, Cedric Klein, Michael Graetzel
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Patent number: 8980444Abstract: A novel iridium complex includes a ligand including a phenyl ring and a pyrazole ring. The phenyl group is bonded to a triazine ring to form a backbone of the novel iridium complex. An organic light-emitting device includes the novel iridium complex.Type: GrantFiled: November 26, 2010Date of Patent: March 17, 2015Assignee: Canon Kabushiki KaishaInventors: Chiaki Nishiura, Masashi Hashimoto, Shigemoto Abe, Hiroya Nitta
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Publication number: 20150073152Abstract: Use of transition metal complexes of the formula (I) in organic light-emitting diodes where: M1 is a metal atom; carbene is a carbene ligand; L is a monoanionic or dianionic ligand; K is an uncharged monodentate or bidentate ligand selected from the group consisting of phosphines; CO; pyridines; nitriles and conjugated dienes which form a n complex with M1; n is the number of carbene ligands and is at least 1; m is the number of ligands L, where m can be 0 or ?1; o is the number of ligands K, where o can be 0 or ?1; where the sum n+m+o is dependent on the oxidation state and coordination number of the metal atom and on the denticity of the ligands carbene, L and K and also on the charge on the ligands carbene and L, with the proviso that n is at least 1, and also an OLED comprising these transition metal complexes, a light-emitting layer comprising these transition metal complexes, OLEDs comprising this light-emitting layer, devices comprising an OLED according to the present invention, and specific trType: ApplicationFiled: November 13, 2014Publication date: March 12, 2015Applicant: BASF SEInventors: Markus BOLD, Christian LENNARTZ, Martina PRINZ, Hans-Werner SCHMIDT, Mukundan THELAKKAT, Markus BAETE, Christian NEUBER, Wolfgang KOWALSKY, Christian SCHILDKNECHT, Hans-Hermann JOHANNES
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Publication number: 20150069334Abstract: Ir/Pt metal complexes, devices containing the Ir/Pt metal complexes, and methods of making such devices are described. The Ir/Pt metal complex includes a first Ir moiety and a first Pt moiety. The first Ir moiety can be an Ir(III) six-coordinated structure. The first Pt moiety can be a Pt(II) four-coordinated tetradentate structure. The devices can have layers that include the Ir/Pt metal complexes. The layers containing the Ir/Pt metal complexes can be made by a solution process.Type: ApplicationFiled: September 9, 2013Publication date: March 12, 2015Applicant: Universal Display CorporationInventors: Chuanjun XIA, Chun Lin
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Patent number: 8975414Abstract: A method for preparing a ruthenium carbene complex precursor includes reacting a ruthenium refinery salt with a hydrogen halide to form a ruthenium intermediate, and reacting the ruthenium intermediate with an L-type ligand to form the ruthenium carbene complex precursor. A method for preparing a ruthenium vinylcarbene complex includes converting a ruthenium carbene complex precursor into a ruthenium hydrido halide complex, and reacting the ruthenium hydrido halide complex with a propargyl halide to form the ruthenium vinylcarbene complex. A method for preparing a ruthenium carbene complex includes converting a ruthenium carbene complex precursor into a ruthenium carbene complex having a structure (PR1R2R3)2Cl2Ru?CH—R4, wherein R1, R2, R3, and R4 are alike or different, and wherein covalent bonds may optionally exist between two or more of R1, R2, and R3 and/or two of R1, R2, and R3 taken together may optionally form a ring with phosphorous.Type: GrantFiled: September 7, 2012Date of Patent: March 10, 2015Assignee: Elevance Renewable Sciences, Inc.Inventors: Linda A. Kunz, Steven A. Cohen