Patents Assigned to Rohm and Haas Electronic Materials, LLC
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Patent number: 11940732Abstract: Coating compositions comprise: a curable compound comprising: a core chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, a C4-30 fused heterocyclic aromatic ring system, C1-20 aliphatic, and C3-20 cycloaliphatic, and three or more substituents of formula (1) wherein at least two substituents of formula (1) are attached to the aromatic core; provided that no substituents of formula (1) are in an ortho position to each other on the same aromatic ring of the core; a polymer; and one or more solvents, wherein the total solvent content is from 50 to 99 wt % based on the coating composition.Type: GrantFiled: April 15, 2021Date of Patent: March 26, 2024Assignee: Rohm and Haas Electronic Materials LLCInventors: Sheng Liu, James F. Cameron, Shintaro Yamada, Iou-Sheng Ke, Keren Zhang, Suzanne M. Coley, Li Cui, Paul J. LaBeaume, Deyan Wang
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Patent number: 11940731Abstract: Photoresist topcoat compositions comprise: a matrix polymer and a surface active polymer, wherein the surface active polymer comprises polymerized units of the following general formula (I): wherein: R1 represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, or a C1-C4 haloalkyl group; R2 independently represents a hydrogen atom or an optionally substituted alkyl group, wherein at least one R2 is not a hydrogen atom, wherein the R2 groups taken together optionally form a cyclic structure, and wherein the total number of carbon atoms for the R2 groups taken together is from 2 to 20; R3 represents an optionally substituted C1-C4 alkylene group, wherein an R2 group optionally forms a cyclic structure with R3; and R4 independently represents C1-C4 fluoroalkyl groups; wherein the total polymerized units of general formula (I) are present in the surface active polymer in an amount of 95 wt % or more based on total polymerized units of the surface active polymer; and wherein the surface active polymer iType: GrantFiled: June 24, 2019Date of Patent: March 26, 2024Assignee: Rohm and Haas Electronic Materials LLCInventors: Irvinder Kaur, Cong Liu, Doris Kang, Chunyi Wu
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Patent number: 11940730Abstract: Disclosed herein is a pattern formation method, comprising (a) applying a layer of a photoresist composition over a semiconductor substrate, (b) pattern-wise exposing the photoresist composition layer to i-line radiation; and (c) developing the exposed photoresist composition layer to provide a resist relief image; wherein the photoresist composition comprises a non-ionic photoacid generator; a solvent; a first polymer and a second polymer; and wherein the first polymer comprises a polymeric dye.Type: GrantFiled: December 29, 2021Date of Patent: March 26, 2024Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Mitsuru Haga, Mingqi Li
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Patent number: 11932713Abstract: New monomer and polymer materials that comprise one or more Te atoms. In one aspect, tellurium-containing monomers and polymers are provided that are useful for Extreme Ultraviolet Lithography.Type: GrantFiled: December 31, 2018Date of Patent: March 19, 2024Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Emad Aqad, James F. Cameron, James W. Thackeray
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Patent number: 11920023Abstract: There is provided a dielectric composite material comprising (a) 20-50 weight % total solids of at least one thermosetting resin and other resin components; and (b) 50-70 weight % total solids of at least one inorganic particulate filler; where the at least one inorganic particulate filler is surface modified with one or more acrylic-based silane coupling agents.Type: GrantFiled: April 28, 2022Date of Patent: March 5, 2024Assignee: Rohm and Haas Electronic Materials LLC.Inventors: Colin Hayes, Colin Calabrese, Christine Hatter
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Patent number: 11906493Abstract: Gas sensors are provided. The gas sensors comprise: a substrate; a plurality of electrodes on the substrate; and a polymeric sensing layer on the substrate for adsorbing a gas-phase analyte. The adsorption of the analyte is effective to change a property of the gas sensor that results in a change in an output signal from the gas sensor. The polymeric sensing layer comprises a polymer chosen from substituted or unsubstituted polyarylenes comprising the reaction product of monomers comprising a first monomer comprising an aromatic acetylene group and a second monomer comprising two or more cyclopentadienone groups, or a cured product of the reaction product. The gas sensors and methods of using such sensors find particular applicability in the sensing of gas-phase organic analytes.Type: GrantFiled: June 23, 2020Date of Patent: February 20, 2024Assignee: Rohm and Haas Electronic Materials LLCInventors: Catherine Mulzer, Christopher D. Gilmore, Hee Jae Yoon, Jaclyn Murphy, Brian Litchfield
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Patent number: 11880135Abstract: Disclosed herein is a method comprising forming a radiation-sensitive film on a substrate; wherein the radiation-sensitive film comprises a radiation-sensitive composition comprising a photoacid generator; a quencher; an acid labile polymer formed from monomers comprising a vinyl aromatic monomer and a monomer comprising an acid decomposable group; and a solvent; patternwise exposing the radiation-sensitive film to activating radiation; and contacting the radiation-sensitive film with an alkaline developing solution to form a resist pattern.Type: GrantFiled: October 15, 2020Date of Patent: January 23, 2024Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Mitsuru Haga, Kunio Kainuma, Shugaku Kushida
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Patent number: 11880134Abstract: New Te-salt compounds, including photoactive tellurium compounds useful for Extreme Ultraviolet Lithography.Type: GrantFiled: November 29, 2018Date of Patent: January 23, 2024Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Emad Aqad, James F. Cameron, James W. Thackeray
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Patent number: 11859082Abstract: Disclosed herein is a copolymer comprising first polymerized units of the formula (1); wherein: R1 is H or a substituted or unsubstituted C1-C6 alkyl group; and R2 is a substituted or unsubstituted C3-C20 alkyl group that optionally includes one or more of —O—, —S—, —N—, —C(O)—, or —C(O)O—, —N—C(O)—, —C(O)—NR—; wherein R is H or a substituted or unsubstituted C1-C6 alkyl group; and second polymerized units of the formula (2): wherein: R3 is a substituted or unsubstituted C1-C6 alkyl group that optionally includes one or more of —O—, —N—, —S—, —C(O)—, or —C(O)O—; wherein the first polymerized units and the second polymerized units are chemically different, and the copolymer is free of fluorine.Type: GrantFiled: December 31, 2020Date of Patent: January 2, 2024Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Mingqi Li, Irvinder Kaur
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Patent number: 11852972Abstract: A photoresist composition, comprising an acid-sensitive polymer comprising a repeating unit having an acid-labile group; an iodonium salt comprising an anion and a cation, the iodonium salt having Formula (1): wherein Z? is an organic anion; Ar1 is substituted or unsubstituted C4-60 heteroaryl group comprising a furan heterocycle; and R1 is substituted or unsubstituted hydrocarbon group as provided herein, wherein the cation optionally comprises an acid-labile group, wherein Ar1 and R1 are optionally connected to each other via a single bond or one or more divalent linking groups to form a ring, and wherein the iodonium salt is optionally covalently bonded through Ar1 or substituent thereof as a pendant group to a polymer, the iodonium salt is optionally covalently bonded through R1 or substituent thereof as a pendant group to a polymer, or the iodonium salt is optionally covalently bonded through Z? as a pendant group to a polymer; and a solvent.Type: GrantFiled: October 30, 2020Date of Patent: December 26, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Tomas Marangoni, Emad Aqad, James W. Thackeray, James F. Cameron, Xisen Hou, ChoongBong Lee
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Patent number: 11846885Abstract: Topcoat compositions are provided that can be used in immersion lithography to form photoresist patterns. The topcoat compositions include a solvent system that comprises 1) a first organic solvent represented by formula (I), wherein R1 and R2 are alkyl groups of 3-8 carbons and the total number of carbons of R1 and R2 is greater than 6; and 2) a second organic solvent that is a C4 to C10 monovalent alcohol.Type: GrantFiled: December 19, 2014Date of Patent: December 19, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS, LLCInventors: Cong Liu, Doris H. Kang, Deyan Wang, Cheng-Bai Xu, Mingqi Li, Chunyi Wu
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Patent number: 11829069Abstract: New photoresist and topcoat compositions are provided that are useful in a variety of applications. In one aspect, new photoresist compositions are provided that comprise: (a) a first matrix polymer; (b) one or more acid generators; and (c) one or more additive compounds of Formulae (I) and/or (II).Type: GrantFiled: December 31, 2018Date of Patent: November 28, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Joshua Kaitz, Tomas Marangoni, Emad Aqad, Amy M. Kwok, Mingqi Li, Thomas Cardolaccia, Choong-Bong Lee, Ke Yang, Cong Liu
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Patent number: 11817316Abstract: Coating compositions comprise: a B-staged reaction product of one or more compounds comprising: a core chosen from C6-50 carbocyclic aromatic, C2-50 heterocyclic aromatic, C1-20 aliphatic, C1-20 heteroaliphatic, C3-20 cycloaliphatic, and C2-20 heterocycloaliphatic, each of which may be substituted or unsubstituted; and two or more substituents of formula (1) attached to the core: wherein: Ar1 is an aromatic group independently chosen from C6-50 carbocyclic aromatic and C2-50 heteroaromatic, each of which may be substituted or unsubstituted; Z is a substituent independently chosen from OR1, protected hydroxyl, carboxyl, protected carboxyl, SR1, protected thiol, —O—C(?O)—C1-6 alkyl, halogen, and NHR2; wherein each R1 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, and C5-30 aryl; each R2 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, C5-30 aryl, C(?O)—R1, and S(?O)2—R1; x is an integer from 1 to the total number of available aromatic ring atoms in Ar1Type: GrantFiled: April 15, 2021Date of Patent: November 14, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Sheng Liu, James F. Cameron, Iou-Sheng Ke, Shintaro Yamada, Li Cui
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Patent number: 11809077Abstract: A photoresist composition comprises a first polymer formed by free radical polymerization. The first polymer comprises polymerized units formed from a monomer that comprises an ethylenically unsaturated double bond and an acid-labile group; a photoacid generator; a quencher of formula (1): and a solvent.Type: GrantFiled: March 11, 2021Date of Patent: November 7, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Thomas Cardolaccia, Jason A. DeSisto, Choong-Bong Lee, Mingqi Li, Tomas Marangoni, Chunyi Wu, Cong Liu, Gregory P. Prokopowicz
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Patent number: 11796916Abstract: A pattern formation method, comprising: (a) providing a semiconductor substrate; (b) forming a photoresist pattern over the semiconductor substrate, wherein the photoresist pattern is formed from a photoresist composition comprising: a first polymer comprising acid labile groups; and a photoacid generator; (c) coating a pattern overcoat composition over the photoresist pattern, wherein the pattern overcoat composition comprises a second polymer and an organic solvent, wherein the organic solvent comprises one or more ester solvents, wherein the ester solvent is of the formula R1—C(O)O—R2, wherein R1 is a C3-C6 alkyl group and R2 is a C5-C10 alkyl group; (d) baking the coated photoresist pattern; and (e) rinsing the coated photoresist pattern with a rinsing agent to remove the second polymer. The methods find particular applicability in the manufacture of semiconductor devices.Type: GrantFiled: April 12, 2021Date of Patent: October 24, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Xisen Hou, Cong Liu, Irvinder Kaur
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Patent number: 11781016Abstract: A UV curable silicone composition has exceptional curability by ultraviolet irradiation.Type: GrantFiled: February 12, 2021Date of Patent: October 10, 2023Assignees: DuPont Toray Specialty Materials Kabushiki Kaisha, Rohm and Haas Electronic Materials LLC, Rohm and Haas Electronic Materials Korea Ltd.Inventors: Shunya Takeuchi, Anna Ya Ching Feng, Yutaka Oka, Jung Hye Chae
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Patent number: 11761107Abstract: Copper electroplating baths include reaction products of amines, polyacrylamides and sultones. The reaction products function as levelers and enable copper electroplating baths which have high throwing power and provide copper deposits with reduced nodules.Type: GrantFiled: January 17, 2020Date of Patent: September 19, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Weijing Lu, Lingli Duan, Zukhra Niazimbetova, Chen Chen, Maria Rzeznik
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Patent number: 11762294Abstract: A photoresist underlayer composition, comprising a polymer comprising a repeating unit of formula (1): wherein Ar is a monocyclic or polycyclic C5-60 aromatic group, wherein the aromatic group comprises one or more aromatic ring heteroatoms, a substituent group comprising a heteroatom, or a combination thereof; R1 is hydrogen, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C1-30 heteroalkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C2-30 heterocycloalkyl, substituted or unsubstituted C2-30 alkenyl, substituted or unsubstituted C2-30 alkynyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C3-30 heteroaryl, or substituted or unsubstituted C4-30 heteroarylalkyl; and R2 is substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C1-30 heteroalkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C2Type: GrantFiled: August 31, 2020Date of Patent: September 19, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Joshua Kaitz, Sheng Liu, Li Cui, Shintaro Yamada, Suzanne M. Coley, Iou-Sheng Ke
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Patent number: 11754927Abstract: Photoresist pattern trimming compositions comprise a polymer, an aromatic sulfonic acid, and an organic-based solvent system, wherein the aromatic sulfonic acid is of general formula (I): wherein: Ar1 represents an aromatic group; R1 independently represents a halogen atom, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted carbocyclic aryl, substituted or unsubstituted heterocyclic aryl, substituted or unsubstituted alkoxy, or a combination thereof, wherein adjacent R1 groups together optionally form a fused ring structure with Ar1; a represents an integer of 2 or more; and b represents an integer of 1 or more, provided that a+b is at least 3 and is not greater than the total number of available aromatic carbon atoms of Ar1, and two or more of R1 are independently a fluorine atom or a fluoroalkyl group bonded directly to an aromatic ring carbon atom.Type: GrantFiled: May 11, 2020Date of Patent: September 12, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Irvinder Kaur, Colin Liu, Xisen Hou, Kevin Rowell, Mingqi Li, Cheng-Bai Xu
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Patent number: 11746184Abstract: Disclosed is a bis-imide compound comprising two or more aryl moieties substituted with ethynyl moieties and the two or more aryl moieties each having one or more polar substituents. Further disclosed is a polymer composition comprising a copolymer polymerized from a monomer mixture of (a) one or more first monomers comprising a bis-imide compound comprising two or more aryl moieties substituted with ethynyl moieties and the two or more aryl moieties each having one or more polar substituents; and (b) one or more second monomers comprising two or more cyclopentadienone moieties. The polymer compositions exhibit favorable properties for use in electronics and displays applications.Type: GrantFiled: November 4, 2020Date of Patent: September 5, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Aaron A. Rachford, Charles R. Kinzie, Michael K. Gallagher, Christopher Gilmore, Young-Seok Kim