From Heterocyclic Compound Containing A Sulfur Atom As A Ring Member Patents (Class 528/377)
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Patent number: 11825732Abstract: 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: GrantFiled: April 23, 2021Date of Patent: November 21, 2023Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
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Patent number: 11739179Abstract: 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 thereofType: GrantFiled: September 29, 2021Date of Patent: August 29, 2023Assignee: AMBILIGHT INC.Inventors: Wenting Wu, Jianguo Mei
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Patent number: 11716895Abstract: 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: GrantFiled: April 23, 2021Date of Patent: August 1, 2023Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
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Patent number: 11682742Abstract: 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: GrantFiled: August 24, 2021Date of Patent: June 20, 2023Assignee: The Regents of the University of CaliforniaInventor: Alexander Ayzner
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Patent number: 11639421Abstract: 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: GrantFiled: April 23, 2021Date of Patent: May 2, 2023Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
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Patent number: 11629231Abstract: 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: GrantFiled: April 23, 2021Date of Patent: April 18, 2023Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
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Patent number: 11499053Abstract: 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: GrantFiled: May 10, 2021Date of Patent: November 15, 2022Assignee: BECTON, DICKINSON AND COMPANYInventors: Glenn P. Bartholomew, Yongchao Liang
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Patent number: 11407913Abstract: 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: GrantFiled: February 26, 2019Date of Patent: August 9, 2022Assignee: AGFA-GEVAERT NVInventors: Johan Loccufier, Rita Torfs
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Patent number: 11398602Abstract: 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: GrantFiled: August 26, 2020Date of Patent: July 26, 2022Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody, Brian J. Worfolk
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Patent number: 11289653Abstract: 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: GrantFiled: August 26, 2020Date of Patent: March 29, 2022Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy A. Repa, Brian J. Worfolk, Alyssa Brooke Chinen-Mendez
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Patent number: 11279673Abstract: 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: GrantFiled: July 6, 2017Date of Patent: March 22, 2022Assignee: SKC CO., LTD.Inventors: Seung Mo Hong, Hyeon Myeong Seo, Jongmin Shim, Sang Mook Kim, Jung Hwan Myung, Junghwan Shin
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Patent number: 11228000Abstract: 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: GrantFiled: August 26, 2020Date of Patent: January 18, 2022Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody
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Patent number: 11211562Abstract: 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: GrantFiled: August 26, 2020Date of Patent: December 28, 2021Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody
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Patent number: 11168178Abstract: 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: GrantFiled: August 26, 2020Date of Patent: November 9, 2021Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody
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Patent number: 11158805Abstract: 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: GrantFiled: August 26, 2020Date of Patent: October 26, 2021Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody
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Patent number: 11034840Abstract: 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: GrantFiled: October 29, 2019Date of Patent: June 15, 2021Assignee: BECTON, DICKINSON AND COMPANYInventors: Glenn P. Bartholomew, Yongchao Liang
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Patent number: 11018302Abstract: 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: GrantFiled: July 7, 2017Date of Patent: May 25, 2021Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
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Patent number: 10955417Abstract: 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: GrantFiled: January 17, 2020Date of Patent: March 23, 2021Assignee: SIRIGEN II LIMITEDInventors: 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
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Patent number: 10804468Abstract: 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: GrantFiled: July 7, 2017Date of Patent: October 13, 2020Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme
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Patent number: 10731005Abstract: 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: GrantFiled: March 24, 2017Date of Patent: August 4, 2020Assignee: KUREHA CORPORATIONInventors: Akihiro Konno, Hiroyuki Sato
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Patent number: 10658593Abstract: 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: GrantFiled: August 29, 2016Date of Patent: May 19, 2020Assignees: LG DISPLAY CO., LTD, LG CHEM, LTD.Inventors: Jungkeun Kim, Dohan Kim, Jeongdae Seo, Hyoseok Kim, Heungwoo Choi, Wanpyo Hong
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Patent number: 10570520Abstract: 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: GrantFiled: February 15, 2018Date of Patent: February 25, 2020Assignee: KEMET Electronics CorporationInventors: Yang Jin, Qingping Chen
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Patent number: 10508173Abstract: 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: GrantFiled: June 10, 2016Date of Patent: December 17, 2019Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yousuke Imagawa, Akinobu Horita, Yoshiaki Yamamoto, Hiroshi Horikoshi
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Patent number: 10439141Abstract: 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: GrantFiled: September 26, 2017Date of Patent: October 8, 2019Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCHInventors: Jun Li, Kok Haw Ong, Zhikuan Chen, Yujun Zhao, Siew Lay Lim, Ivy Wong, Le Yang, Kang Yee Seah
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Patent number: 10396286Abstract: 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: GrantFiled: November 22, 2013Date of Patent: August 27, 2019Assignee: The Regents of the University of CaliforniaInventors: Guillermo C. Bazan, Lei Ying, Ben B. Y. Hsu, Wen Wen, Hsin-Rong Tseng, Gregory C. Welch
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Patent number: 10377895Abstract: 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: GrantFiled: March 19, 2015Date of Patent: August 13, 2019Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVESInventors: Alexandre Carella, Nicolas Massonnet, Jean-Pierre Simonato
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Patent number: 10361370Abstract: 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: GrantFiled: July 7, 2017Date of Patent: July 23, 2019Assignee: Phillips 66 CompanyInventors: Hualong Pan, Kathy Woody, Brian Worfolk, Taeshik Earmme, Joseph E. Bullock
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Patent number: 10312445Abstract: 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: GrantFiled: May 24, 2016Date of Patent: June 4, 2019Assignee: LG Chem, Ltd.Inventors: Bogyu Lim, Jaechol Lee, Doowhan Choi, Sungkyoung Kang
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Patent number: 10294326Abstract: 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: GrantFiled: May 22, 2015Date of Patent: May 21, 2019Assignee: UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INCORPORATEDInventors: John Robert Reynolds, Michael R. Craig, Aubrey Lynn Dyer, Justin Adam Kerszulis
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Patent number: 10211401Abstract: 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: GrantFiled: February 3, 2015Date of Patent: February 19, 2019Assignee: TOYOBO CO., LTD.Inventors: Atsushi Wakamiya, Kazutake Hagiya, Shiro Hamamoto, Hikaru Tanaka
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Patent number: 10208147Abstract: 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: GrantFiled: December 6, 2012Date of Patent: February 19, 2019Assignee: Solvay Specialty Polymers Italy S.P.A.Inventors: Ivan Wlassics, Vito Tortelli, Alessio Marrani
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Patent number: 10062851Abstract: 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: GrantFiled: December 12, 2016Date of Patent: August 28, 2018Assignee: FUJIFILM CORPORATIONInventors: Toshihiro Kariya, Kensuke Masui, Takafumi Nakayama, Shuji Kanayama, Hiroyuki Takahashi
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Patent number: 9799831Abstract: 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: GrantFiled: December 27, 2013Date of Patent: October 24, 2017Assignee: Agency for Science, Technology and ResearchInventors: Jun Li, Kok Haw Ong, Zhikuan Chen, Yujun Zhao, Siew Lay Lim, Ivy Wong, Lee Yang, Kang Yee Seah
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Patent number: 9718905Abstract: 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: GrantFiled: July 3, 2013Date of Patent: August 1, 2017Assignee: TOSOH CORPORATIONInventors: Hirokazu Yano, Masakazu Nishiyama, Hiroshi Awano
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Patent number: 9658364Abstract: 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: GrantFiled: September 24, 2013Date of Patent: May 23, 2017Assignee: KOC SOLUTION CO., LTD.Inventors: Dong Gyu Jang, Soo Gyun Roh, Jong Hyo Kim, Bong-Keun So, Jin-Moo Seo
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Patent number: 9634253Abstract: 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: GrantFiled: June 16, 2015Date of Patent: April 25, 2017Assignee: GWANGJU INSTITUTE OF SCIENCE AND TECHNOLOGYInventors: Jae-Suk Lee, Moon-Ho Ham, Myungwoo Son, Walaa Ahmed Ahmed Elsawy, Myung-Jin Kim
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Patent number: 9627621Abstract: 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: GrantFiled: April 28, 2014Date of Patent: April 18, 2017Assignee: Agency for Science, Technology and ResearchInventors: Zhikuan Chen, Jun Li, Beng Ong, Samarendra P. Singh, Hoi Kai Ivy Wong, Kok Haw Ong
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Patent number: 9472764Abstract: 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: GrantFiled: March 15, 2013Date of Patent: October 18, 2016Assignees: Northwestern University, Polyera CorporationInventors: Tobin J. Marks, Xugang Guo, Nanjia Zhou, Robert P. H. Chang, Martin Drees, Antonio Facchetti
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Patent number: 9453102Abstract: 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: GrantFiled: October 20, 2014Date of Patent: September 27, 2016Assignee: University of Washington through its Center for CommercializationInventors: Christine Keiko Luscombe, Ken Okamoto
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Patent number: 9412950Abstract: 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: GrantFiled: September 24, 2012Date of Patent: August 9, 2016Assignee: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Yasunori Uetani, Ken Yoshimura
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Patent number: 9365679Abstract: 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: GrantFiled: November 30, 2012Date of Patent: June 14, 2016Assignees: 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
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Patent number: 9337358Abstract: Benzodithiophene-containing polymers, as well as related photovoltaic cells, articles, systems, and methods, are disclosed.Type: GrantFiled: July 5, 2012Date of Patent: May 10, 2016Assignee: MERCK PATENT GMBHInventors: Paul Byrne, Kap-Soo Cheon, Gilles Dennler, Nicolas Drolet, Serge Thompson, David Waller, Li Wen
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Patent number: 9328203Abstract: 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: GrantFiled: November 30, 2012Date of Patent: May 3, 2016Assignees: 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
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Patent number: 9328204Abstract: 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: GrantFiled: November 30, 2012Date of Patent: May 3, 2016Assignees: 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
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Patent number: 9328194Abstract: 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: GrantFiled: December 3, 2012Date of Patent: May 3, 2016Assignees: 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
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Patent number: 9318707Abstract: 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: GrantFiled: November 14, 2012Date of Patent: April 19, 2016Assignee: KONICA MINOLTA, INC.Inventors: Takamune Hattori, Yasushi Okubo
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Patent number: 9312492Abstract: 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: GrantFiled: February 9, 2015Date of Patent: April 12, 2016Assignee: RAYNERGY TEK INC.Inventors: Martin Drees, Hualong Pan, Zhihua Chen, Shaofeng Lu, Antonio Facchetti
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Patent number: 9312491Abstract: 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: GrantFiled: September 3, 2013Date of Patent: April 12, 2016Assignees: JX NIPPON OIL & ENERGY CORPORATION, NATIONAL UNIVERSITY CORPORATION OF HIROSHIMA UNIVERSITYInventors: Seunghun Eu, Tsuyoshi Asano, Itaru Osaka, Kazuo Takimiya
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Patent number: 9221944Abstract: 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: GrantFiled: December 16, 2009Date of Patent: December 29, 2015Assignees: BASF SE, Polyera CorporationInventors: Ashok Kumar Mishra, Subramanian Vaidyanathan, Hiroyoshi Noguchi, Florian Doetz, Silke Koehler, Marcel Kastler
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Patent number: 9147843Abstract: 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: GrantFiled: April 16, 2013Date of Patent: September 29, 2015Assignee: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Hiroki Terai