From Heterocyclic Compound Containing A Sulfur Atom As A Ring Member Patents (Class 528/377)
  • Patent number: 11825732
    Abstract: A random copolymer comprising the monomer units A, B and C. In this random copolymer A comprises B comprises and C comprises an aryl group. Additionally, R1 R2, R3 and R4 are side chains independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups. X1 and X2 are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups.
    Type: Grant
    Filed: April 23, 2021
    Date of Patent: November 21, 2023
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
  • Patent number: 11739179
    Abstract: The present disclosure presents a disulfide containing monomer, its reduced form, its derivative, the synthesis method of this disulfide containing monomer, and the polymer containing the monomers disclosed thereof
    Type: Grant
    Filed: September 29, 2021
    Date of Patent: August 29, 2023
    Assignee: AMBILIGHT INC.
    Inventors: Wenting Wu, Jianguo Mei
  • Patent number: 11716895
    Abstract: A random copolymer comprising the monomer units A, B and C. In this random copolymer A comprises B comprises and C comprises an aryl group. Additionally, R1, R2, R3 and R4 are side chains independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups. X1 and X2 are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups.
    Type: Grant
    Filed: April 23, 2021
    Date of Patent: August 1, 2023
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
  • Patent number: 11682742
    Abstract: The present invention generally relates to artificial photosystems and methods of their use, for example in artificial photosynthesis, wherein the artificial photosystems comprise one or more light-harvesting antenna (LHA) comprising a conjugated polyelectrolyte (CPE) complex (CPEC) comprising a donor CPE and an acceptor CPE, wherein the donor CPE and acceptor CPE are an electronic energy transfer (EET) donor/acceptor pair.
    Type: Grant
    Filed: August 24, 2021
    Date of Patent: June 20, 2023
    Assignee: The Regents of the University of California
    Inventor: Alexander Ayzner
  • Patent number: 11639421
    Abstract: A random copolymer comprising the monomer units A and B. In this random copolymer A comprises and B comprises Additionally, R1 R2, R3 and R4 are side chains independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups. X1 and X2 are different and at least one is a Cl and the other is selected from the group consisting of: H, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups.
    Type: Grant
    Filed: April 23, 2021
    Date of Patent: May 2, 2023
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
  • Patent number: 11629231
    Abstract: A random copolymer comprising the monomer units A and B. In this random copolymer A comprises and B comprises Additionally, R1 R2, R3 and R4 are side chains independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups. X1 and X2 are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups.
    Type: Grant
    Filed: April 23, 2021
    Date of Patent: April 18, 2023
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
  • Patent number: 11499053
    Abstract: Water soluble polymeric dyes and polymeric tandem dyes are provided. The polymeric dyes include a water solvated light harvesting multichromophore having a conjugated segment of aryl or heteroaryl co-monomers including branched non-ionic water soluble groups (WSG) comprising two or more water soluble polymers. In some cases, the branched non-ionic water soluble groups (WSG) of the present disclosure are capable of imparting solubility in water in excess of 50 mg/mL to the multichromophore. The polymeric tandem dyes further include a signaling chromophore covalently linked to the multichromophore in energy-receiving proximity therewith. Also provided are aggregation-resistant labelled specific binding members that include the subject water soluble polymeric dyes. Methods of evaluating a sample for the presence of a target analyte and methods of labelling a target molecule in which the subject polymeric dyes find use are also provided. Systems and kits for practicing the subject methods are also provided.
    Type: Grant
    Filed: May 10, 2021
    Date of Patent: November 15, 2022
    Assignee: BECTON, DICKINSON AND COMPANY
    Inventors: Glenn P. Bartholomew, Yongchao Liang
  • Patent number: 11407913
    Abstract: A method of manufacturing a Printed Circuit Board (PCB) wherein an inkjet printing step is used, characterized in that in the inkjet printing step a radiation curable inkjet ink comprising an adhesion promoter having a chemical structure according to Formula I is jetted and cured on a substrate, wherein X is selected from the group consisting of O and NR3, L1 and L2 independently represent a divalent linking group comprising from 2 to 20 carbon atoms, R1 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group, R2 is selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkaryl group, a substituted or unsubstituted aralkyl group and a substituted or unsubstituted (hetero)aryl group, R3 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group,
    Type: Grant
    Filed: February 26, 2019
    Date of Patent: August 9, 2022
    Assignee: AGFA-GEVAERT NV
    Inventors: Johan Loccufier, Rita Torfs
  • Patent number: 11398602
    Abstract: An organic compound comprising: In this organic compound, W is selected from the group consisting of: S, Se, O, and N-Q; and Q is selected from the group consisting of: a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring. Additionally, in this organic compound Ar1 and Ar2 are independently selected from the group selected from: H, an aryl group, and a heteroaryl group.
    Type: Grant
    Filed: August 26, 2020
    Date of Patent: July 26, 2022
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody, Brian J. Worfolk
  • Patent number: 11289653
    Abstract: A method of reacting bis(R1) 5,5??-dibromo-3?,4?-difluoro-[2,2?:5?,2?:5?,2??-quaterthiophene]-3,3??-dicarboxylate and bis(R2) 5,5??-dibromo-3?,4?-difluoro-[2,2?:5?,2?:5?,2??-quaterthiophene]-3,3??-dicarboxylate to form the polymer: In this polymer R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of: a halogen, a substituted alkyl, an unsubstituted alkyl, a substituted aryl, an unsubstituted aryl, a substituted heteroaryl and an unsubstituted heteroaryl.
    Type: Grant
    Filed: August 26, 2020
    Date of Patent: March 29, 2022
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy A. Repa, Brian J. Worfolk, Alyssa Brooke Chinen-Mendez
  • Patent number: 11279673
    Abstract: An embodiment relates to an aromatic polythiol compound for optical materials, and the aromatic polythiol compound according to the embodiment contains a phenyl group and a large number of sulfur atoms in its polythiol structure so that a polymerizable composition and an optical material obtained therefrom have excellent optical properties such as high refractive index and low specific gravity, as well as excellent mechanical properties such as low cure shrinkage; thus, they can be advantageously used for producing various plastic optical lenses such as eyeglass lenses and camera lenses.
    Type: Grant
    Filed: July 6, 2017
    Date of Patent: March 22, 2022
    Assignee: SKC CO., LTD.
    Inventors: Seung Mo Hong, Hyeon Myeong Seo, Jongmin Shim, Sang Mook Kim, Jung Hwan Myung, Junghwan Shin
  • Patent number: 11228000
    Abstract: A polymer comprising wherein Ar1 and Ar2 are optional and either the same or different and independently selected from an aryl group or an heteroaryl group. In this polymer, W is selected from the group consisting of: S, Se, O, and N-Q; and Q is selected from the group consisting of: a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring. Additionally, in the polymer, R1 is selected from the group consisting of: a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring and wherein x+y=1.
    Type: Grant
    Filed: August 26, 2020
    Date of Patent: January 18, 2022
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody
  • Patent number: 11211562
    Abstract: A method of forming a polymer, the method comprising combining 4-bromo-7-[5-bromo-4-(alkyl)thiophen-2-yl]-6-chloro-5-fluoro-2,1,3-benzothiadiazole, (3,3?-difluoro-[2,2?-bithiophene]-5,5?-diyl)bis(trimethylstannane), [4-(alkyl)-5-[5-(trimethylstannyl)thiophen-2-yl]thiophen-2-yl]trimethylstannane, tris(dibenzylideneacetone), and dipalladium P(o-tol)3 tris(2-methylphenyl)phosphane to form the polymer: In this polymer, W is selected from the group consisting of: S, Se, O, and N-Q. Additionally, Q is selected from the group consisting of: a straight-chain carbyl, silyl or hydrocarbyl, branched, cyclic alkyl with 1 to 30 atoms, and fused aromatic rings.
    Type: Grant
    Filed: August 26, 2020
    Date of Patent: December 28, 2021
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody
  • Patent number: 11168178
    Abstract: A method of forming a polymer, the method comprising combining 4,7-bis(5-bromo-4-alkyl thiophen-2-yl)-5-chloro-6-fluorobenzo[c][1,2,5]thiadiazole, (3,3?-difluoro-[2,2?-bithiophene]-5,5?-diyl)bis(trimethylstannane), and benzo[1,2-b:4,5-b?]dithiophene-2,6-diyl)bis(trimethylstannane), Pd2dba3 and P(o-tol)3 to form the polymer: In this polymer, W is selected from the group consisting of: S, Se, O, and N-Q. Additionally, in this polymer Q is selected from the group consisting of: a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring.
    Type: Grant
    Filed: August 26, 2020
    Date of Patent: November 9, 2021
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody
  • Patent number: 11158805
    Abstract: A method of forming a polymer, the method begins by combining 4,7-bis(5-bromo-4-alkylthiophen-2-yl)-5-chloro-6-fluorobenzo[c][1,2,5]thiadiazole, [4-alkyl-5-[5-(trimethylstannyl)thiophen-2-yl]thiophen-2-yl]trimethylstannane, (3,3?-difluoro-[2,2?-bithiophene]-5,5?-diyl)bis(trimethylstannane), Pd2dba3 and P(o-tol)3 to form the polymer: In this polymer R1 and R2 are independently selected from the group consisting of a straight-chain or branched carbyl, silyl, or hydrocarbyl, a branched or cyclic alkyl with 1 to 30 atoms, a fused substituted aromatic ring, and a fused unsubstituted aromatic ring; and the ratio of x is between 0.6 to 0.8 and y is between 0.2 and 0.4.
    Type: Grant
    Filed: August 26, 2020
    Date of Patent: October 26, 2021
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody
  • Patent number: 11034840
    Abstract: Water soluble polymeric dyes and polymeric tandem dyes are provided. The polymeric dyes include a water solvated light harvesting multichromophore having a conjugated segment of aryl or heteroaryl co-monomers including branched non-ionic water soluble groups (WSG) comprising two or more water soluble polymers. In some cases, the branched non-ionic water soluble groups (WSG) of the present disclosure are capable of imparting solubility in water in excess of 50 mg/mL to the multichromophore. The polymeric tandem dyes further include a signaling chromophore covalently linked to the multichromophore in energy-receiving proximity therewith. Also provided are aggregation-resistant labelled specific binding members that include the subject water soluble polymeric dyes. Methods of evaluating a sample for the presence of a target analyte and methods of labelling a target molecule in which the subject polymeric dyes find use are also provided. Systems and kits for practicing the subject methods are also provided.
    Type: Grant
    Filed: October 29, 2019
    Date of Patent: June 15, 2021
    Assignee: BECTON, DICKINSON AND COMPANY
    Inventors: Glenn P. Bartholomew, Yongchao Liang
  • Patent number: 11018302
    Abstract: A random copolymer comprising the monomer units A, B and C. In this random copolymer A comprises B comprises and C comprises an aryl group. Additionally, R1 R2, R3 and R4 are side chains independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups. X1 and X2 are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups.
    Type: Grant
    Filed: July 7, 2017
    Date of Patent: May 25, 2021
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
  • Patent number: 10955417
    Abstract: Described herein are methods, compositions and articles of manufacture involving neutral conjugated polymers including methods for synthesis of neutral conjugated water-soluble polymers with linkers along the polymer main chain structure and terminal end capping units. Such polymers may serve in the fabrication of novel optoelectronic devices and in the development of highly efficient biosensors. The invention further relates to the application of these polymers in assay methods.
    Type: Grant
    Filed: January 17, 2020
    Date of Patent: March 23, 2021
    Assignee: SIRIGEN II LIMITED
    Inventors: Brent S. Gaylord, Glenn P. Bartholomew, Russell A. Baldocchi, Janice W. Hong, William H. Huisman, Yongchao Liang, Trung Nguyen, Lan T. Tran, Jean M. Wheeler, Adrian Charles Vernon Palmer, Frank Peter Uckert
  • Patent number: 10804468
    Abstract: A molecular complex comprising wherein X1 and X2 are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups; R1, R2, R1? and R2? are side chains independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups; R3 are selected from the group consisting of alkyl group, alkoxy group, aryl groups and combinations thereof; and wherein the thiophene groups are unsymmetrical.
    Type: Grant
    Filed: July 7, 2017
    Date of Patent: October 13, 2020
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
  • Patent number: 10731005
    Abstract: The present invention provides a method for producing granular polyarylene sulfide (PAS) with increased average particle size and enhanced particle strength, a method for increasing the average particle size of granular PAS, a method for enhancing the particle strength of granular PAS, and granular PAS.
    Type: Grant
    Filed: March 24, 2017
    Date of Patent: August 4, 2020
    Assignee: KUREHA CORPORATION
    Inventors: Akihiro Konno, Hiroyuki Sato
  • Patent number: 10658593
    Abstract: An organic light emitting display device is provided. The organic light emitting display device may include at least one light emitting part between an anode and a cathode, and the at least one light emitting part having at least one organic layer and a light emitting layer, wherein the at least one organic layer comprises a compound represented by Chemical Formula 1 or 2.
    Type: Grant
    Filed: August 29, 2016
    Date of Patent: May 19, 2020
    Assignees: LG DISPLAY CO., LTD, LG CHEM, LTD.
    Inventors: Jungkeun Kim, Dohan Kim, Jeongdae Seo, Hyoseok Kim, Heungwoo Choi, Wanpyo Hong
  • Patent number: 10570520
    Abstract: An improved process for forming a conjugated thiophene precursor is described as in the formation of an improved polymer prepared from the conjugated thiophene and an improved capacitor formed from the improved polymer. The improved process includes forming a thiophene mixture comprising thiophene monomer, unconjugated thiophene oligomer, optionally a solvent and heating the thiophene mixture at a temperature of at least 100° C. to no more than the lower of 250° C. or the boiling point of a component of said thiophene mixture with the lowest boiling point temperature.
    Type: Grant
    Filed: February 15, 2018
    Date of Patent: February 25, 2020
    Assignee: KEMET Electronics Corporation
    Inventors: Yang Jin, Qingping Chen
  • Patent number: 10508173
    Abstract: The present invention provides a composition for an optical material containing a ring compound (a) represented by formula (1), an episulfide compound (b), and sulfur (c), wherein the content of the ring compound (a) in the composition for an optical material is in the range of 5-70 mass %, the content of the episulfide compound (b) is in the range of 20-90 mass %, and the content of the sulfur (c) is in the range of 1-39 mass %. (In the formula, X represents S, Se or Te. a to f=0 to 3, 8?(a+c+e)?1, 8?(b+d+f)?2, and (b+d+f)?(a+c+e).) This composition for an optical material has a high refractive index as an optical characteristic, and has sufficient heat resistance and good mold release characteristics.
    Type: Grant
    Filed: June 10, 2016
    Date of Patent: December 17, 2019
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yousuke Imagawa, Akinobu Horita, Yoshiaki Yamamoto, Hiroshi Horikoshi
  • Patent number: 10439141
    Abstract: There is provided p-type organic polymers of general formula I. The polymers may be useful as semi-conducting material. Thus, thin films and devices comprising such polymers are also provided.
    Type: Grant
    Filed: September 26, 2017
    Date of Patent: October 8, 2019
    Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH
    Inventors: Jun Li, Kok Haw Ong, Zhikuan Chen, Yujun Zhao, Siew Lay Lim, Ivy Wong, Le Yang, Kang Yee Seah
  • Patent number: 10396286
    Abstract: A method of regioselectively preparing a pyridine-containing compound is provided. In particular embodiments, the method includes reacting halogen-functionalized pyridal[2,1,3]thiadiazole with organotin-functionalized cyclopenta[2,1-b:3,4-b?]dithiophene or organotin-functionalized indaceno[2,1-b:3,4-b?]dithiophene. Also provided is a method of preparing a polymer. The method includes regioselectively preparing a monomer that includes a pyridal[2,1,3]thiadiazole unit; and reacting the monomer to produce a polymer that includes a regioregular conjugated backbone section, wherein the section includes a repeat unit containing the pyridal[2,1,3]thiadiazole unit. A polymer that includes a regioregular conjugated backbone section, and electronic devices that include the polymer, are also provided.
    Type: Grant
    Filed: November 22, 2013
    Date of Patent: August 27, 2019
    Assignee: The Regents of the University of California
    Inventors: Guillermo C. Bazan, Lei Ying, Ben B. Y. Hsu, Wen Wen, Hsin-Rong Tseng, Gregory C. Welch
  • Patent number: 10377895
    Abstract: The present invention relates to a conductive polymer material of poly(thio- or seleno-)phene type containing at least two distinct species of counteranion, including a first species which is an anionic form of sulphuric acid, and a second species of counteranion selected from triflate, triflimidate, tosylate, mesylate, perchlorate and hexafluorophosphate. The invention also relates to a process for preparing such a material and the use thereof as conductive film. The invention also targets a substrate coated at least partly by a film of a material as defined above, a device comprising a material as defined above as conductive material, and also the use thereof in the organic electronics, organic thermoelectricity, organic photovoltaic and organic photodetector fields.
    Type: Grant
    Filed: March 19, 2015
    Date of Patent: August 13, 2019
    Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES
    Inventors: Alexandre Carella, Nicolas Massonnet, Jean-Pierre Simonato
  • Patent number: 10361370
    Abstract: An organic photovoltaic device comprising an electron transport layer disposed between an anode and a polymer layer. In this organic photovoltaic device the polymer layer can also be disposed between the electron transport layer and a cathode. The electron transport layer comprises (AOx)yBO(1-y) with an optional fullerene dopant. The polymer comprises a molecular complex comprising wherein X1 and X2 are independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, ester, ketone, amide and aryl groups; R1, R2, R1? and R2? are side chains independently selected from the group consisting of: H, Cl, F, CN, alkyl, alkoxy, alkylthio, ester, ketone and aryl groups; R3 are selected from the group consisting of alkyl group, alkoxy group, aryl groups and combinations thereof; G is an aryl group; and wherein the thiophene groups are unsymmetrical.
    Type: Grant
    Filed: July 7, 2017
    Date of Patent: July 23, 2019
    Assignee: Phillips 66 Company
    Inventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme, Joseph E. Bullock
  • Patent number: 10312445
    Abstract: The present specification relates to a polymer, which comprises an electron acceptor functional group on a side chain and is represented by chemical formula 1 below, and to an organic electronic element comprising the same.
    Type: Grant
    Filed: May 24, 2016
    Date of Patent: June 4, 2019
    Assignee: LG Chem, Ltd.
    Inventors: Bogyu Lim, Jaechol Lee, Doowhan Choi, Sungkyoung Kang
  • Patent number: 10294326
    Abstract: Copolymers including dioxythiophene repeating units and no acceptor units allow the formation of electrochromic polymers (ECPs) with vivid neutral state colors and very colorless oxidized states that can be switched rapidly. The dioxythiophene repeating units can included in sequences where all of one type of dioxythiophene is included exclusively as isolated dyads or triads within the copolymer, or the copolymer can be an alternating copolymer with propylenedioxythiophene units. Other non-acceptor units can be included in the copolymers. The copolymers are rendered organic solvent soluble by alkyl substituents on repeating units. The inclusion of sterically encumbered acyclic dioxythiophene (AcDOT) units promotes red color while unsubstituted ethylenedioxythiophene (EDOT) units promote blue colors, and their respective content can be manipulated to achieve a desired neutral state color. Soluble copolymers comprising at least 50% EDOT repeating units can be used in supercapacitor applications.
    Type: Grant
    Filed: May 22, 2015
    Date of Patent: May 21, 2019
    Assignee: UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INCORPORATED
    Inventors: John Robert Reynolds, Michael R. Craig, Aubrey Lynn Dyer, Justin Adam Kerszulis
  • Patent number: 10208147
    Abstract: This invention pertains to fluoroallylsulfonyl azide compounds of formula: CF2?CF—CF2—Rf—SO2N3 formula (I) wherein Rf is a divalent (per)fluorinated group, optionally comprising one or more than one ethereal oxygen atom [monomer (Az)], which are useful as functional monomers in fluoropolymers, to the fluoropolymers which comprise recurring units derived from such fluoroallylsulfonyl azide compounds, to a process for their manufacture, to a curable compound comprising the same and to a method for crosslinking the same.
    Type: Grant
    Filed: December 6, 2012
    Date of Patent: February 19, 2019
    Assignee: Solvay Specialty Polymers Italy S.P.A.
    Inventors: Ivan Wlassics, Vito Tortelli, Alessio Marrani
  • Patent number: 10211401
    Abstract: Provided are: a macromolecular compound for providing an organic semiconductor material exhibiting excellent conversion efficiency; a starting-material compound having high material design freedom; and methods for producing the same. The macromolecular compound according to the present invention comprising a benzobisthiazole structural unit represented by the formula (1): [in the formula (1), T1 and T2 each independently represent an alkoxy group, a thioalkoxy group, a thiophene ring optionally substituted by a hydrocarbon group or an organosilyl group, a thiazole ring optionally substituted by a hydrocarbon group or an organosilyl group, or a phenyl group optionally substituted by a hydrocarbon group, an alkoxy group, a thioalkoxy group, an organosilyl group, a halogen atom or a trifluoromethyl group; and B1 and B2 each represent a thiophene ring optionally substituted by a hydrocarbon group, a thiazole ring optionally substituted by a hydrocarbon group, or an ethynylene group].
    Type: Grant
    Filed: February 3, 2015
    Date of Patent: February 19, 2019
    Assignee: TOYOBO CO., LTD.
    Inventors: Atsushi Wakamiya, Kazutake Hagiya, Shiro Hamamoto, Hikaru Tanaka
  • Patent number: 10062851
    Abstract: An object of the present invention is to provide a composition for forming an organic semiconductor film that makes it possible to obtain an organic semiconductor film having excellent mobility and heat stability, an organic semiconductor element including an organic semiconductor film having excellent mobility and heat stability, and a method for manufacturing the organic semiconductor element.
    Type: Grant
    Filed: December 12, 2016
    Date of Patent: August 28, 2018
    Assignee: FUJIFILM CORPORATION
    Inventors: Toshihiro Kariya, Kensuke Masui, Takafumi Nakayama, Shuji Kanayama, Hiroyuki Takahashi
  • Patent number: 9799831
    Abstract: There is provided p-type organic polymers of general formula I. The polymers may be useful as semi-conducting material. Thus, thin films and devices comprising such polymers are also provided.
    Type: Grant
    Filed: December 27, 2013
    Date of Patent: October 24, 2017
    Assignee: Agency for Science, Technology and Research
    Inventors: Jun Li, Kok Haw Ong, Zhikuan Chen, Yujun Zhao, Siew Lay Lim, Ivy Wong, Lee Yang, Kang Yee Seah
  • Patent number: 9718905
    Abstract: To provide a water-soluble polythiophene used as an electrically conductive material, and its production method. A polythiophene comprising at least one type of structural units selected from the group consisting of structural units represented by the formula (1), structural units represented by the formula (2), structural units represented by the formula (3), structural units represented by the formula (4), structural units represented by the formula (5) and structural units represented by the formula (6). The polythiophene is obtained by polymerizing at least one thiophene compound selected from the group consisting of a thiophene compound represented by the formula (15), a thiophene compound represented by the formula (16) and a thiophene compound represented by the formula (17) in water or an alcohol solvent in the presence of an oxidizing agent.
    Type: Grant
    Filed: July 3, 2013
    Date of Patent: August 1, 2017
    Assignee: TOSOH CORPORATION
    Inventors: Hirokazu Yano, Masakazu Nishiyama, Hiroshi Awano
  • Patent number: 9658364
    Abstract: Disclosed is a method of storing a thioepoxy compound and a method of preparing a thioepoxy based optical material using the thioepoxy compound. Particularly, a method of preparing a high-quality thioepoxy based optical material having superior color and thermal stability and less time-dependent change, and being colorless and transparent by inhibiting time-dependent change of the thioepoxy compound during storage is disclosed. In addition, a method of storing the thioepoxy compound for an optical material, the thioepoxy compound having a water content of 500 to 2,500 ppm and stored at ?78 to 10° C., and a method of preparing the thioepoxy based optical material, the method including polymerizing a polymerizable composition including the stored thioepoxy compound, are provided. The high-quality thioepoxy based optical material, which is colorless and transparent, prepared according to the present invention may be broadly used in a variety of fields as a substitute for conventional optical materials.
    Type: Grant
    Filed: September 24, 2013
    Date of Patent: May 23, 2017
    Assignee: KOC SOLUTION CO., LTD.
    Inventors: Dong Gyu Jang, Soo Gyun Roh, Jong Hyo Kim, Bong-Keun So, Jin-Moo Seo
  • Patent number: 9634253
    Abstract: Disclosed herein are a donor-acceptor conjugated polymer and an organic electronic device including the same. According to embodiments of the invention, it is possible to realize a conjugated polymer suitable for organic memory devices and a multi-functional, high-performance, large-area organic memory device for electronics including the same, the organic memory device operating in air.
    Type: Grant
    Filed: June 16, 2015
    Date of Patent: April 25, 2017
    Assignee: GWANGJU INSTITUTE OF SCIENCE AND TECHNOLOGY
    Inventors: Jae-Suk Lee, Moon-Ho Ham, Myungwoo Son, Walaa Ahmed Ahmed Elsawy, Myung-Jin Kim
  • Patent number: 9627621
    Abstract: A polymer comprises a polymeric chain represented by formula (I) or (II). In formula (I) a, b, d, and n are integers, a from 0 to 3, b from 1 to 5, c from 1 to 3, d from 1 to 5, and n from 2 to 5000; R1 and R2 are side chains; R3 and R4 are each independently H or a side chain; and when a is 0, R3 and R4 are side chains. In formula (II), a, b, c, d, e, and n are integers, a from 1 to 3, b and c being independently 0 or 1, d and e being independently 1 or 2, and n from 2 to 5000; R1 and R2 are side chains except —COOalkyl; and X1, X2 and X3 are independently O, S, or Se. Semiconductors and devices comprising the polymer are also provided.
    Type: Grant
    Filed: April 28, 2014
    Date of Patent: April 18, 2017
    Assignee: Agency for Science, Technology and Research
    Inventors: Zhikuan Chen, Jun Li, Beng Ong, Samarendra P. Singh, Hoi Kai Ivy Wong, Kok Haw Ong
  • Patent number: 9472764
    Abstract: The present invention relates to certain polymeric compounds and their use as organic semiconductors in organic and hybrid optical, optoelectronic, and/or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The present compounds can provide improved device performance, for example, as measured by power conversion efficiency, fill factor, open circuit voltage, field-effect mobility, on/off current ratios, and/or air stability when used in photovoltaic cells or transistors. The present compounds can have good solubility in common solvents enabling device fabrication via solution processes.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: October 18, 2016
    Assignees: Northwestern University, Polyera Corporation
    Inventors: Tobin J. Marks, Xugang Guo, Nanjia Zhou, Robert P. H. Chang, Martin Drees, Antonio Facchetti
  • Patent number: 9453102
    Abstract: Methods for the preparation of mono- and bis-end-functionalized ?-conjugated polymers. In the methods, chalcogens are selectively installed at the polymer terminus or termini.
    Type: Grant
    Filed: October 20, 2014
    Date of Patent: September 27, 2016
    Assignee: University of Washington through its Center for Commercialization
    Inventors: Christine Keiko Luscombe, Ken Okamoto
  • Patent number: 9412950
    Abstract: A polymer compound comprising a repeating unit represented by the formula (A) and a repeating unit represented by the formula (B) manifests large absorbance of light having long wavelength, and can be used in an organic photoelectric conversion device and an organic thin film transistor. [in the formula (A) and the formula (B), R represents a hydrogen atom, a fluorine atom, an optionally substituted alkyl group, an alkoxy group optionally substituted by a fluorine atom, an aryl group, a heteroaryl group, a group represented by the formula (2a) or a group represented by the formula (2b). A plurality of R may be the same or mutually different. Ar1 and Ar2 represent an optionally substituted tri-valent aromatic hydrocarbon group having 6 to 60 carbon atoms or a trivalent heterocyclic group having 4 to 60 carbon atoms.].
    Type: Grant
    Filed: September 24, 2012
    Date of Patent: August 9, 2016
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Yasunori Uetani, Ken Yoshimura
  • Patent number: 9365679
    Abstract: The present invention relates to a benzodithiophene based copolymer containing thieno[3,4-b]thiophene units and a preparing method and applications thereof. The polymer has a structural formula (I), wherein R1 and R2 are respectively selected from H, and alkyl groups of C1 to C16; R3 and R4 are respectively selected from H, alkyl groups of C1 to C16, alkoxy groups of C1 to C16, or thiophene groups substituted by alkyl groups of C1 to C16; R5 is selected from alkyl groups of C1 to C16; n is a natural number from 7 to 80. Applications of the benzodithiophene based copolymer containing thieno[3,4-b]thiophene units in polymer solar cells, polymer organic light-emission, polymer organic field effect transistors, polymer organic optical storage, polymer organic nonlinear materials or polymer organic laser are also provided.
    Type: Grant
    Filed: November 30, 2012
    Date of Patent: June 14, 2016
    Assignees: OCEAN'S LIGHTING SCIENCE & TECHNOLOGY CO., LTD., SHENZHEN OCEAN'S KING LIGHTING ENGINEERING CO., LTD.
    Inventors: Mingjie Zhou, Rong Guan, Manyuan Li, Jiale Huang, Naiyuan Li
  • Patent number: 9337358
    Abstract: Benzodithiophene-containing polymers, as well as related photovoltaic cells, articles, systems, and methods, are disclosed.
    Type: Grant
    Filed: July 5, 2012
    Date of Patent: May 10, 2016
    Assignee: MERCK PATENT GMBH
    Inventors: Paul Byrne, Kap-Soo Cheon, Gilles Dennler, Nicolas Drolet, Serge Thompson, David Waller, Li Wen
  • Patent number: 9328204
    Abstract: A benzodithiophene based copolymer containing thiophene pyrroledione units, a preparing method thereof, and applications of the copolymer in polymer solar cells, organic light-emitting, organic field effect transistors, organic optical storage, organic nonlinear materials or organic laser.
    Type: Grant
    Filed: November 30, 2012
    Date of Patent: May 3, 2016
    Assignees: OCEAN'S KING LIGHTING SCIENCE & TECHNOLOGY CO., LTD., SHENZHEN OCEAN'S KING LIGHTING ENGINEERING CO., LTD.
    Inventors: Mingjie Zhou, Rong Guan, Manyuan Li, Jiale Huang, Naiyuan Li
  • Patent number: 9328203
    Abstract: The present invention relates to a benzodithiophene based copolymer containing pyridino[2,1,3]thiadiazole units and a preparing method and applications thereof. The polymer has a structural formula (I), wherein R1 and R2 are respectively selected from H or alkyl groups of C1 to C16; R3 and R4 are respectively selected from H, alkyl groups of C1 to C16, alkoxy groups of C1 to C16, or thiophene groups substituted by alkyl groups of C1 to C16; X is N and Y is CH, or X is CH and Y is N; and n is a natural number of 7 to 80. Applications of the benzodithiophene based copolymer containing pyridino[2,1,3]thiadiazole units in polymer solar cells, polymer organic light-emitting, polymer organic field effect transistors, polymer organic optical storage, polymer organic nonlinear materials or polymer organic laser are also provided.
    Type: Grant
    Filed: November 30, 2012
    Date of Patent: May 3, 2016
    Assignees: OCEAN'S KING LIGHTING SCIENCE & TECHNOLOGY CO., LTD., SHENZHEN OCEAN'S KING LIGHTING ENGINEERING CO., LTD.
    Inventors: Mingjie Zhou, Rong Guan, Manyuan Li, Jiale Huang, Naiyuan Li
  • Patent number: 9328194
    Abstract: The present invention relates to a benzodithiophene based copolymer containing isoindoline-1,3-diketone units and a preparing method and applications thereof. The polymer has a structural formula (I), wherein R1 and R2 are respectively selected from H or alkyl groups of C1 to C16; R3 and R4 are respectively selected from H, alkyl groups of C1 to C16, alkoxy groups of C1 to C16, or thiophene groups substituted by alkyl groups of C1 to C16; R5 is selected from alkyl groups of C1 to C16; n is a natural number from 7 to 80. Applications of the benzodithiophene based copolymer containing isoindoline-1,3-diketone units in polymer solar cells, polymer organic light-emitting, polymer organic field effect transistors, polymer organic optical storage, polymer organic nonlinear materials or polymer organic laser are also provided.
    Type: Grant
    Filed: December 3, 2012
    Date of Patent: May 3, 2016
    Assignees: OCEAN'S KING LIGHTING SCIENCE & TECHNOLOGY CO., LTD., SHENZHEN OCEAN'S KING LIGHTING ENGINEERING CO., LTD.
    Inventors: Mingjie Zhou, Rong Guan, Manyuan Li, Jiale Huang, Naiyuan Li
  • Patent number: 9318707
    Abstract: An organic photoelectric conversion element which sequentially comprises a transparent first electrode, a photoelectric conversion layer that contains a p-type organic semiconductor material and an n-type organic semiconductor material, and a second electrode in this order on a transparent substrate.
    Type: Grant
    Filed: November 14, 2012
    Date of Patent: April 19, 2016
    Assignee: KONICA MINOLTA, INC.
    Inventors: Takamune Hattori, Yasushi Okubo
  • Patent number: 9312492
    Abstract: The present invention relates to all-polymer blends including an electron-acceptor polymer and an electron-donor polymer, capable of providing improved device performance, for example, as measured by power conversion efficiency, when used in photovoltaic cells.
    Type: Grant
    Filed: February 9, 2015
    Date of Patent: April 12, 2016
    Assignee: RAYNERGY TEK INC.
    Inventors: Martin Drees, Hualong Pan, Zhihua Chen, Shaofeng Lu, Antonio Facchetti
  • Patent number: 9312491
    Abstract: A photoelectric conversion element has a structure where a hole transport layer, a photoelectric conversion layer, and an electron transport layer are held between a first electrode and a second electrode. The photoelectric conversion layer is a bulk heterojunction layer, and fullerene or a fullerene derivative is used as an n-type organic semiconductor. As a p-type organic semiconductor, a polymer represented by the following Expression is used. In the Expression, R1, R2, R3, and R4 each independently represent any one of a branched alkyl group, a linear alkyl group, an alkyl ester group, a carboxy alkyl group, and an alkoxy group. Independently, X is any one of S, O, and N.
    Type: Grant
    Filed: September 3, 2013
    Date of Patent: April 12, 2016
    Assignees: JX NIPPON OIL & ENERGY CORPORATION, NATIONAL UNIVERSITY CORPORATION OF HIROSHIMA UNIVERSITY
    Inventors: Seunghun Eu, Tsuyoshi Asano, Itaru Osaka, Kazuo Takimiya
  • Patent number: 9221944
    Abstract: Disclosed are new semiconductor materials prepared from dithienylvinylene copolymers with aromatic or heteroaromatic ?-conjugated systems. Such copolymers, with little or no post-deposition heat treatment, can exhibit high charge carrier mobility and/or good current modulation characteristics. In addition, the polymers of the present teachings can possess certain processing advantages such as improved solution-processability and low annealing temperature.
    Type: Grant
    Filed: December 16, 2009
    Date of Patent: December 29, 2015
    Assignees: BASF SE, Polyera Corporation
    Inventors: Ashok Kumar Mishra, Subramanian Vaidyanathan, Hiroyoshi Noguchi, Florian Doetz, Silke Koehler, Marcel Kastler
  • Patent number: 9147843
    Abstract: A compound represented by the formula (1). A polymer compound comprising the compound. An organic semiconductor material comprising the compound or the polymer compound. An organic semiconductor device comprising an organic layer comprising the organic semiconductor material. An organic transistor comprising a source electrode, a drain electrode, a gate electrode and an active layer, wherein the active layer comprises the organic semiconductor material.
    Type: Grant
    Filed: April 16, 2013
    Date of Patent: September 29, 2015
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Hiroki Terai