Patents Examined by Marie R. Yamnitzky
  • Patent number: 9793498
    Abstract: It is an object of the present invention to provide an organometallic complex that can emit phosphorescence. In the following general formula (G1), X represents —O— or —N(R10)—. R1 to R9 each represent any of hydrogen, an alkyl group or a cycloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, an acyloxy group having 1 to 6 carbon atoms, a halogen group, a haloalkyl group, and an aryl group having 6 to 12 carbon atoms. In addition, R10 represents any of an alkyl group or a cycloalkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 4 to 10 carbon atoms. Moreover, M represents an element belonging to Group 9 or 10.
    Type: Grant
    Filed: June 16, 2016
    Date of Patent: October 17, 2017
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Hideko Inoue, Masakazu Egawa, Satoshi Seo
  • Patent number: 9783564
    Abstract: Novel phosphorescent tetradentate platinum compounds of Formula I are provided. The complexes contain a dibenzo moiety, which allows for the creation of OLED devices with improved properties when compounds of Formula I are incorporated into such devices. Compounds of Formula I? that comprise two ligands that contain a 5-membered carbocyclic or heterocyclic ring, one of which contains an imidazole ring with a twisted aryl group attached to N?1 and a second aromatic ring that is attached to the platinum via a carbon atom. These compounds may be advantageously used in OLEDs.
    Type: Grant
    Filed: August 17, 2012
    Date of Patent: October 10, 2017
    Assignee: UNIVERSAL DISPLAY CORPORATION
    Inventors: Gregg Kottas, James Fiordeliso, Bin Ma, Chuanjun Xia, Scott Beers, Jason Brooks
  • Patent number: 9780322
    Abstract: An organic electroluminescent element includes a hole injection layer (HI), a first hole transport layer (HT1), a second hole transport layer (HT2), and a light-emitting layer containing a host compound (H) and a phosphorescence emitting dopant compound (D), which are laminated in this order, between and an anode and a cathode. The phosphorescence emitting dopant compound has a partial structure represented by Formula (1): The “highest occupied molecular orbital” HOMO of the second hole transport layer satisfies the expression: ?5.4<HOMO (HT2)<?4.8; and the relationship of triplet excitation energies (T1) between the phosphorescence emitting dopant compound and a hole transport material contained in the second hole transport layer satisfies the expression: T1 (HT2)?T1 (D)>0.1.
    Type: Grant
    Filed: October 2, 2012
    Date of Patent: October 3, 2017
    Assignee: KONICA MINOLTA, INC.
    Inventors: Kunio Tani, Eisaku Katoh, Hiroto Ito, Kunimasa Hiyama
  • Patent number: 9773986
    Abstract: Devices comprising an organic light emitting device are provided. The devices can include an anode; a cathode; and an organic layer, disposed between the anode and the cathode. The organic layer comprising at least one host material comprising a phosphorescent complex comprising novel phosphorescent trigonal copper carbene complexes. The complex comprise a carbene ligand coordinated to a three coordinate copper atom. The complex may be used in organic light emitting devices. In particular, the complexes may be especially useful in OLEDs used for lighting applications.
    Type: Grant
    Filed: October 22, 2013
    Date of Patent: September 26, 2017
    Assignee: THE UNIVERSITY OF SOUTHERN CALIFORNIA
    Inventors: Mark Thompson, Peter Djurovich, Valentina Krylova
  • Patent number: 9773981
    Abstract: Composition for use in an organic light-emitting device, the composition having a fluorescent light-emitting material and a triplet-accepting material subject to the following energetic scheme: 2×T1A>S1A>S1E, or T1A+T1E>S1A>S1E in which: T1A represents a triplet excited state energy level of the triplet-accepting material; TIE represents a triplet excited state energy level of the light-emitting material; S1A represents a singlet excited state energy level of the triplet-accepting material; and S1E represents a singlet excited state energy level of the light-emitting material; and in which light emitted by the composition upon excitation includes delayed fluorescence.
    Type: Grant
    Filed: June 24, 2011
    Date of Patent: September 26, 2017
    Assignees: Cambridge Display Technology, Ltd., Sumitomo Chemical Company Limited
    Inventors: Simon King, Martina Pintani, Matthew Roberts, Michael Cass
  • Patent number: 9768396
    Abstract: A tris-type iridium complex in which a ligand having a distinctive nitrogen-containing five-membered heterocyclic skeleton is coordinated is provided. The ligand has a nitrogen-containing five-membered heterocyclic skeleton composed of 2 to 4 nitrogen atoms and one or more carbon atoms. In the skeleton, an aryl group is bonded to a carbon atom on both sides of which nitrogen atoms are positioned, and a tricycloalkyl group having a bridge structure and having 9 or 10 carbon atoms is bonded to one of the two nitrogen atoms positioned on both the sides of the carbon atom. The tricycloalkyl group having a bridge structure and having 9 or 10 carbon atoms may be an adamantyl group or a noradamantyl group.
    Type: Grant
    Filed: December 20, 2012
    Date of Patent: September 19, 2017
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Hideko Inoue, Yui Yamada, Nobuharu Ohsawa, Satoshi Seo
  • Patent number: 9741947
    Abstract: An organometallic complex represented by Formula 1 below and an organic light-emitting device including the same: Formula 1 is as defined in the specification.
    Type: Grant
    Filed: March 31, 2014
    Date of Patent: August 22, 2017
    Assignees: Samsung Display Co., Ltd., Korea Advanced Institute of Science and Technology
    Inventors: Youn-Sun Kim, Yun-Ho Lee, Seul-Ong Kim, Dong-Woo Shin, Jung-Sub Lee, Naoyuki Ito, Chang-Woong Chu, Yeong-Eun Kim
  • Patent number: 9735374
    Abstract: A metal complex exhibits blue light emission of high color purity and has a color purity of small temperature dependence, particularly in the blue region. Specifically, the metal complex is represented by Formula (1a): wherein M is a metal atom; R0 is a divalent linking group; each j independently represents 0 or 1; RP1, RP2, RP3, RP4 and RP6 each independently represents a hydrogen atom or the like; RP5 represents a halogen atom or the like; m is an integer of from 1 to 3, n is an integer of from 0 to 2, and m+n is 2 or 3; and the portion represented by Formula (2): represents a bidentate ligand; wherein Rx and Ry are an atom bonding to the metal atom M, and each independently represents a carbon atom, an oxygen atom or a nitrogen atom.
    Type: Grant
    Filed: January 10, 2013
    Date of Patent: August 15, 2017
    Assignees: SUMITOMO CHEMICAL COMPANY, LIMITED, NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY
    Inventors: Nobuhiko Akino, Taichi Abe, Hideo Konno, Shigeru Shimada, Kazuhiko Sato
  • Patent number: 9735375
    Abstract: There is provided a compound having Formula I In the formula: R1 can be aryl, alkyl, silyl, or deuterated analogs thereof; R2 can be aryl, alkyl, silyl, or deuterated analogs thereof; R3 can be H, D, alkyl, silyl, deuterated alkyl, or deuterated silyl; and R4 is the same or different at each occurrence and is H, D, aryl, alkyl, silyl, deuterated aryl, deuterated alkyl, or deuterated silyl.
    Type: Grant
    Filed: March 21, 2013
    Date of Patent: August 15, 2017
    Assignee: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Norman Herron, Weiying Gao
  • Patent number: 9735377
    Abstract: Iridium complexes with ligands containing twisted aryl groups having extended conjugation (i.e., the twisted aryl is substituted with an additional aryl group) and organic light emitting devices including the same are disclosed. The iridium complexes can be used in organic light emitting devices may provide improved stability color, lifetime and manufacturing.
    Type: Grant
    Filed: December 30, 2016
    Date of Patent: August 15, 2017
    Assignee: UNIVERSAL DISPLAY CORPORATION
    Inventors: Chuanjun Xia, Walter Yeager, Bin Ma, Scott Beers, Jui-Yi Tsai, James Fiordeliso, Edward Barron, Chun Lin
  • Patent number: 9705097
    Abstract: A highly stable metal complex useful for the manufacture of a light-emitting device has an excellent lifetime property, particularly in a blue region, specifically a metal complex represented by Formula (1): wherein M is a metal atom; each R0 independently represents a divalent linking group; i and j each independently represent 0 or 1; RP1, RP2, RP3, RP4, RP5 and RP6 each independently represent a hydrogen atom and the like, with a proviso that at least one of RP1, RP2, RP3, RP4, RP5 and RP6 is a dendron; m is an integer of from 1 to 3, n is an integer of from 0 to 2, and m+n is 2 or 3; and the portion represented by Formula (2): represents a bidentate ligand; wherein Rx and Ry are an atom bonding to the metal atom M, and each independently represents a carbon atom and the like.
    Type: Grant
    Filed: January 10, 2013
    Date of Patent: July 11, 2017
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Nobuhiko Akino, Taichi Abe, Hideo Konno, Shigeru Shimada, Kazuhiko Sato
  • Patent number: 9692000
    Abstract: Disclosed is an organic electroluminescent element having high luminous efficiency and long life. Also disclosed are a display device and an illuminating device respectively using such an organic electroluminescent element. Specifically disclosed is an organic electroluminescent element comprising an electrode and at least one or more organic layers on a substrate. This organic electroluminescent element is characterized in that at least one of the organic layers is a light-emitting layer containing a phosphorescent compound and a host compound, the phosphorescent compound has a HOMO of ?5.15 to ?3.50 eV and a LUMO of from ?1.25 to +1.00 eV, and the host compound has a 0-0 band of the phosphorescence spectrum at not more than 460 nm and a glass transition temperature of not less than 60° C.
    Type: Grant
    Filed: May 16, 2013
    Date of Patent: June 27, 2017
    Assignee: KONICA MINOLTA, INC.
    Inventors: Shinya Otsu, Hiroshi Kita, Eisaku Katoh
  • Patent number: 9673405
    Abstract: An organic electroluminescent device containing: a six-coordinate, ortho-metalated iridium complex represented by the formula (I): wherein V represents a trivalent linking group and is bound to L1 to L3 through covalent bonds; each of L1 to L3 is represented by the formula (II) and R1 represents a substituted aryl group having seven or more carbon atoms.
    Type: Grant
    Filed: September 19, 2011
    Date of Patent: June 6, 2017
    Assignee: KONICA MINOLTA HOLDINGS, INC.
    Inventors: Noriko Yasukawa, Dai Ikemizu, Tomohiro Oshiyama, Masato Nishizeki, Tatsuo Tanaka
  • Patent number: 9673406
    Abstract: Novel organic compounds comprising a boron-nitrogen heterocycle are provided. In particular, the compound contains an azaborine. The compounds may be used in organic light emitting devices to provide devices having improved photophysical and electronic properties.
    Type: Grant
    Filed: October 11, 2013
    Date of Patent: June 6, 2017
    Assignee: UNIVERSAL DISPLAY CORPORATION
    Inventors: Raymond Kwong, Bin Ma, Jui-Yi Tsai, Scott Beers, Ed Barron, Gregg Kottas, Alexey Dyatkin
  • Patent number: 9673407
    Abstract: A compound including a ligand L according to Formula I: as well as, a first device and a formulation containing the same, are disclosed. In the compound including the Ligand L of Formula I: R1 and R2 are independently selected from 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, cyano, and combinations thereof; two adjacent substituents of R1 or R2 are optionally joined to form a fused ring; ligand L is coordinated to transition metal M having an atomic number greater than 40; R1 represent mono, di, tri, or tetra-substitution, or no substitution; R2 represent mono, di, or tri-substitution, or no substitution; and at least one substituent of R1 or R2 is cyano.
    Type: Grant
    Filed: February 28, 2014
    Date of Patent: June 6, 2017
    Assignee: UNIVERSAL DISPLAY CORPORATION
    Inventors: Geza Szigethy, Christopher B. Murray, Jason Brooks
  • Patent number: 9670404
    Abstract: Compounds comprising the formula L1L2MX wherein L1, L2, and X are distinct bidentate ligands that form an octahedral complex on the metal M, wherein M is a metal with an atomic weight greater than 40. Compounds of this formula are sublimated more facilely than octahedral metal complexes where L1, L2, and X are not distinct bidentate ligands. Organic light emitting devices are also described wherein the emissive layer may comprise a host material containing an emissive molecule of formula L1L2MX, which molecule is adapted to luminesce when a voltage is applied across the heterostructure, and the emissive molecule is selected from the group of phosphorescent organometallic complexes, including iridium complexes of the formula L1L2IrX wherein L1, L2, and X are distinct bidentate ligands.
    Type: Grant
    Filed: July 6, 2012
    Date of Patent: June 6, 2017
    Assignee: UNIVERSAL DISPLAY CORPORATION
    Inventors: Chuanjun Xia, Bin Ma, Alan DeAngelis
  • Patent number: 9663544
    Abstract: Heteroleptic cyclometallated complexes having a 6-membered ring cyclometallated to the metal, as shown in Formula (I), are provided: wherein ring A and ring B are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; wherein L1 is BR, NR, PR, O, S, Se, C?O, S?O, SO2, CRR?, SiRR?, or GeRR; wherein Z1 and Z2 are independently carbon or nitrogen; wherein at least one of Z1 and Z2 is carbon; wherein is a bidentate ligand selected from the group consisting of: wherein R1, R2, Ra, Rb, Rc, and Rd may represent mono, di, tri, or tetra substitution, or no substitution; wherein R1, R2, R, R?, Ra, Rb, Rc, and Rd are each independently selected from various substituents; and wherein n is 1 or 2. Devices, such as organic light emitting devices (OLEDs) that comprise phosphorescent light emitting materials are also provided.
    Type: Grant
    Filed: July 25, 2012
    Date of Patent: May 30, 2017
    Assignee: UNIVERSAL DISPLAY CORPORATION
    Inventors: Jui-Yi Tsai, Gregg Kottas
  • Patent number: 9634268
    Abstract: Electronic devices, in particular organic electroluminescent devices, comprising metal complexes of the formula (1).
    Type: Grant
    Filed: November 9, 2010
    Date of Patent: April 25, 2017
    Assignee: Merck Patent GmbH
    Inventors: Philipp Stoessel, Dominik Joosten, Esther Breuning
  • Patent number: 9634276
    Abstract: Disclosed is an organic electroluminescent element having high luminous efficiency and long life. Also disclosed are a display device and an illuminating device respectively using such an organic electroluminescent element. Specifically disclosed is an organic electroluminescent element comprising an electrode and at least one or more organic layers on a substrate. This organic electroluminescent element is characterized in that at least one of the organic layers is a light-emitting layer containing a phosphorescent compound and a host compound, the phosphorescent compound has a HOMO of ?5.15 to ?3.50 eV and a LUMO of from ?1.25 to +1.00 eV, and the host compound has a 0-0 band of the phosphorescence spectrum at not more than 460 nm and a glass transition temperature of not less than 60° C.
    Type: Grant
    Filed: May 16, 2013
    Date of Patent: April 25, 2017
    Assignee: KONICA MINOLTA, INC.
    Inventors: Shinya Otsu, Hiroshi Kita, Eisaku Katoh
  • Patent number: 9634265
    Abstract: Novel organic compounds comprising ligands with deuterium substitution are provided. In particular, the compound is an iridium complex comprising methyl-d3 substituted ligands. The compounds may be used in organic light emitting devices to provide devices having improved color, efficiency and lifetime.
    Type: Grant
    Filed: August 6, 2013
    Date of Patent: April 25, 2017
    Assignee: Universal Display Corporation
    Inventors: Chuanjun Xia, James Fiordeliso, Raymond Kwong