Nitrogen In Heterocyclic Ring Patents (Class 430/920)
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Patent number: 12098262Abstract: A method for isolating plastic products produced by polymerization of resin with proton beams is disclosed. The method comprises a liquid resin added with a reactive dye that changes from transparent or colorless to color when activated by the proton beam or the chemical polymerization process to reveal polymerization within a polymerizable resin. The change in color is correlated to the energy delivered to the resin by a proton beam, electromagnetic radiation, or heat. The reactive dye is placed into a plastic container. The proton beam is directed into the container to polymerize the resin. When irradiation is complete, the container of frozen resin is opened at the top and bottom and placed on top of the column of water containing a density gradient provided by dissolved salt. The partially cured product is fully cured while suspended in the density gradient by application of heat or ultraviolet radiation.Type: GrantFiled: September 19, 2022Date of Patent: September 24, 2024Inventor: George Edward Parris
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Patent number: 12065521Abstract: A radical polymerization method may use a compound having a polycyclic aromatic skeleton and an endoperoxide compound having a polycyclic aromatic skeleton. An endoperoxide compound may have a polycyclic aromatic skeleton of formula (1), and a compound may have a polycyclic aromatic skeleton, which is a raw material of the endoperoxide compound: wherein R is a C1-10 alkyl group, an alkoxymethyl group having a C1-5 alkoxy group, a C6-10 aryl group, an alkylcarbonyl group having a C1-10 alkyl group, an arylcarbonyl group having a C6-20 aryl group, an alkyloxycarbonyl group having a C1-10 alkyl group, an aryloxycarbonyl group having a C6-10 aryl group, an alkyloxycarbonylmethyl group having a C1-12 alkyl group or an aryloxycarbonylmethyl group having a C6-12 aryl group.Type: GrantFiled: February 12, 2019Date of Patent: August 20, 2024Assignees: Kawasaki Kasei Chemicals Ltd., National University Corporation YOKOHAMA National UniversityInventors: Shunichi Himori, Keita Iuchi, Akihiko Yamada, Hiroaki Gotoh, Kazuhisa Sakakibara
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Patent number: 11993005Abstract: A process, an apparatus, and photoswitchable photoinitiators for polymerizing a starting material by dual color photopolymerization. In particular, photoinitiators are provided, which cause curing of photopolymerizable formulations upon illumination with two different wavelengths.Type: GrantFiled: April 21, 2023Date of Patent: May 28, 2024Assignee: xolo GmBHInventors: Yves Garmshausen, Marcus Reuter, Marin Regehly, Dirk Radzinski
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Patent number: 11919997Abstract: A white photosensitive resin composition, a white spacer, a light conversion layer, and a light-emitting device are provided. The white photosensitive resin composition includes a polymerizable compound (A), an alkali-soluble resin (B), a photopolymerization initiator (C), a solvent (D), and a white pigment (E). The polymerizable compound (A) includes an ethylenically-unsaturated monomer (A-1) represented by formula (I-1) and a thiol compound (A-2) having two or more thiol groups in one molecule, wherein based on 100 mass % of the polymerizable compound (A), a total content of the ethylenically-unsaturated monomer (A-1) and the thiol compound (A-2) is 10 mass % to 98 mass %.Type: GrantFiled: May 25, 2021Date of Patent: March 5, 2024Assignee: eChem Solutions Corp.Inventors: Meng-Po Liu, Yu-Chun Chen
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Patent number: 11762288Abstract: A resist composition that generates an acid upon exposure and whose solubility in a developing solution is changed by action of an acid.Type: GrantFiled: December 10, 2020Date of Patent: September 19, 2023Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroto Yamazaki, Seiji Todoroki, Masahiro Shiosaki, Nobuhiro Michibayashi
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Patent number: 11567409Abstract: A polymer comprising a first repeating unit including an amino group protected by an alkoxycarbonyl group; a second repeating unit including a nucleophilic group; and a third repeating unit including a crosslinkable group, wherein the first repeating unit, the second repeating unit, and the third repeating unit are different from each other.Type: GrantFiled: April 17, 2020Date of Patent: January 31, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.Inventors: Jung June Lee, Suwoong Kim, Min Kyung Jang, Jin Hong Park, Jae Hwan Sim, Jae Bong Lim
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Patent number: 9029070Abstract: There are provided a method of forming a resist pattern includes: a step (1) in which a resist composition containing a base component (A) that generates base upon exposure and exhibits increased solubility in an alkali developing solution by the action of acid is applied to a substrate to form a resist film; a step (2) in which the resist film 2 is subjected to exposure; a step (3) in which baking is conducted after the step (2); and a step (4) in which the resist film 2 is subjected to an alkali development, thereby forming a negative-tone resist pattern in which the unexposed portion 2b of the resist film 2 has been dissolved and removed, and the resist composition used in the step (1).Type: GrantFiled: November 2, 2012Date of Patent: May 12, 2015Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito
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Patent number: 9023585Abstract: A resist composition which generates a base upon exposure and exhibits increased solubility in an alkali developing solution under the action of acid, and the resist composition including: a base component (A) that exhibits increased solubility in an alkali developing solution under the action of acid; an acidic compound component (G1) including a nitrogen-containing cation having a pKa value of 7 or less and a counteranion; and a buffer component (K) including a nitrogen-containing cation and a counteranion being a conjugate base for the acid having a pKa value of 0 to 5.Type: GrantFiled: June 20, 2013Date of Patent: May 5, 2015Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito, Hiroaki Shimizu
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Patent number: 9023581Abstract: A resist composition which can form a very fine resist pattern with excellent lithography properties, a new polymeric compound useful for the resist composition, and a compound useful as a monomer for the polymeric compound. The resist composition contains a polymeric compound containing a structural unit (a0) represented by general formula (a0) shown below. In the formula (a0), A is an anion represented by the general formula (1) or (2).Type: GrantFiled: June 14, 2011Date of Patent: May 5, 2015Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Akiya Kawaue, Kazushige Dohtani, Yoshiyuki Utsumi, Jun Iwashita, Kenri Konno, Daiju Shiono, Daichi Takaki
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Patent number: 8956806Abstract: A method and material layer for forming a pattern are disclosed. The method includes providing a substrate; forming a first material layer over the substrate; forming a second material layer over the first material layer, wherein the second material layer comprises a photoacid generator and a photobase generator; and exposing one or more portions of the second material layer.Type: GrantFiled: September 18, 2009Date of Patent: February 17, 2015Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.Inventors: Chien-Wei Wang, Ching-Yu Chang, Burn Jeng Lin
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Patent number: 8932797Abstract: A photoacid generator compound has formula (I): G+Z???(I) wherein G has formula (II): In formula (II), X is S or I, each R0 is commonly attached to X and is independently C1-30 alkyl; polycyclic or monocyclic C3-30 cycloalkyl; polycyclic or monocyclic C6-30 aryl; or a combination comprising at least one of the foregoing groups. G has a molecular weight greater than 263.4 g/mol, or less than 263.4 g/mol. One or more R0 groups are further attached to an adjacent R0 group, a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 2 or 3. Z in formula (I) comprises the anion of a sulfonic acid, a sulfonimide, or a sulfonamide. A photoresist and coated film also includes the photoacid generator, and a method of forming an electronic device uses the photoresist.Type: GrantFiled: November 30, 2011Date of Patent: January 13, 2015Assignees: Dow Global Technologies LLC, Rohm and Haas Electronic Materials LLCInventors: James W. Thackeray, Suzanne M. Coley, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour, Owendi Ongayi, Vipul Jain
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Patent number: 8921028Abstract: A salt represented by the formula (I) and a resist composition containing the salt are provided, wherein Q1, Q2, L1, ring W1, Re1, Re2, Re3, Re4, Re5, Re6, Re7, Re8, Re9, Re10, Re11, Re12, Re13 and Z are defined in the specification.Type: GrantFiled: March 7, 2012Date of Patent: December 30, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Koji Ichikawa
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Patent number: 8906591Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.Type: GrantFiled: September 14, 2012Date of Patent: December 9, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8883395Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.Type: GrantFiled: September 14, 2012Date of Patent: November 11, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8871429Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.Type: GrantFiled: September 14, 2012Date of Patent: October 28, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8852846Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C20 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, W represents a group represented by the formula (W1), (W2), (W3), (W4) or (W5): and Z+ represents an organic counter ion.Type: GrantFiled: April 4, 2012Date of Patent: October 7, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Yukako Anryu, Koji Ichikawa
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Patent number: 8846301Abstract: An orthogonal process for photolithographic patterning organic structures is disclosed. The disclosed process utilizes fluorinated solvents or supercritical CO2 as the solvent so that the performance of the organic conductors and semiconductors would not be adversely affected by other aggressive solvent. One disclosed method may also utilize a fluorinated photoresist together with the HFE solvent, but other fluorinated solvents can be used. In one embodiment, the fluorinated photoresist is a resorcinarene, but various fluorinated polymer photoresists and fluorinated molecular glass photoresists can be used as well. For example, a copolymer perfluorodecyl methacrylate (FDMA) and 2-nitrobenzyl methacrylate (NBMA) is a suitable orthogonal fluorinated photoresist for use with fluorinated solvents and supercritical carbon dioxide in a photolithography process.Type: GrantFiled: May 21, 2009Date of Patent: September 30, 2014Assignee: Cornell UniversityInventors: Christopher K. Ober, George Malliaras, Jin-Kyun Lee, Alexander Zakhidov, Margarita Chatzichristidi, Priscilla Taylor
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Patent number: 8846291Abstract: A resist composition including: a base component (A) which exhibits changed solubility in a developing solution under action of acid; a nitrogen-containing organic compound component (C) containing a compound (C1) represented by general formula (c1) shown below; and an acid generator component (B) which generates acid upon exposure, provided that the compound (C1) is excluded from the acid generator component (B): wherein RN represents a nitrogen-containing heterocyclic group which may have a substituent; X0 represents a linear or branched divalent aliphatic hydrocarbon group of 1 to 10 carbon atoms, a cyclic divalent aliphatic hydrocarbon group of 3 to 20 carbon atoms or a divalent aliphatic hydrocarbon group of 3 to 20 carbon having a cyclic partial structure, or any one of these groups in which some or all of the hydrogen atoms thereof have been substituted with fluorine atoms; and M+ represents an organic cation.Type: GrantFiled: December 6, 2011Date of Patent: September 30, 2014Assignee: Tokyo Ohka Kogyo Co. Ltd.Inventors: Yoshiyuki Utsumi, Kenichiro Miyashita, Akiya Kawaue
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Patent number: 8846296Abstract: A composition is provided. The composition includes a polymer and a photosensitive acid generator capable of generating a first amount of acid upon exposure to a first dose of radiation and a second amount of acid upon exposure to a second dose of radiation. The second amount of acid is greater than the first amount of acid. The second dose is greater than the first dose. The composition includes a photosensitive base generator capable of generating a first amount of base upon exposure to the first dose and a second amount of base upon exposure to the second dose, where the first amount of base is greater than the first amount of acid and the second amount of base is less than the second amount of acid. The photosensitive base generator may include benzoin carbamates, O-carbamoylhydroxylamines, O-carbamoyloximes, aromatic sulfonamides, ?-lactones, N-(2-Arylethenyl)amides, azides, amides, oximines, quaternary ammonium salts, or amineimides.Type: GrantFiled: May 2, 2012Date of Patent: September 30, 2014Assignee: International Business Machines CorporationInventors: Kuang-Jung Chen, Wu-Song Huang, Ranee Wai-Ling Kwong, Sen Liu, Pushkara R. Varanasi
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Patent number: 8835095Abstract: A resist composition contains (A1) a resin having a structural unit represented by the formula (I), (A2) a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid, (B) an acid generator, and (D) at least one compound selected from the group consisting of a compound represented by the formula (II1) and a compound represented by the formula (II2), wherein R1, A1, R2, R6, X1, X2, R3, R4 and R5 are defined in the specification.Type: GrantFiled: February 24, 2012Date of Patent: September 16, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Hiromu Sakamoto, Yuichi Mukai
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Patent number: 8735047Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, A13, A14, X12, Q1, Q2, L1, ring W1 and Z+ are defined in the specification.Type: GrantFiled: July 18, 2012Date of Patent: May 27, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Satoshi Yamaguchi
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Patent number: 8709700Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.Type: GrantFiled: September 13, 2012Date of Patent: April 29, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8703384Abstract: A positive resist composition comprising (A) a polymer comprising recurring units of a specific structure adapted to generate an acid in response to high-energy radiation and acid labile units, the polymer having an alkali solubility that increases under the action of an acid, and (B) a sulfonium salt of a specific structure exhibits a high resolution in forming fine size patterns, typically trench patterns and hole patterns. Lithographic properties of profile, DOF and roughness are improved.Type: GrantFiled: November 23, 2011Date of Patent: April 22, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tomohiro Kobayashi, Eiji Fukuda, Takayuki Nagasawa, Ryosuke Taniguchi, Youichi Ohsawa, Masayoshi Sagehashi, Yoshio Kawai
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Patent number: 8697332Abstract: An object of the present invention is to provide a base generator which has sensitivity and is applicable to a wide range of applications, and a photosensitive resin composition which is applicable to a wide range of applications due to the structure of a polymer precursor in which reaction into a final product is promoted by a basic substance or by heating in the presence of a basic substance. The base generator generates a base by exposure to electromagnetic radiation and heating. The photosensitive resin composition comprises a polymer precursor in which reaction into a final product is promoted by the base generator and a basic substance or by heating in the presence of a basic substance.Type: GrantFiled: March 26, 2010Date of Patent: April 15, 2014Assignee: Dai Nippon Printing Co., Ltd.Inventors: Mami Katayama, Shunji Fukuda, Katsuya Sakayori, Kouji Kawaguchi
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Patent number: 8663899Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator, wherein R1, A1, R2, Rb1, Rb2, Lb1, ring Wb1, Rb3, Rb4, and Z1+ are defined in the specification.Type: GrantFiled: July 18, 2012Date of Patent: March 4, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Takashi Hiraoka, Hiromu Sakamoto
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Patent number: 8663901Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.Type: GrantFiled: September 13, 2012Date of Patent: March 4, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8652753Abstract: A resist composition having; a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), an acid generator, and a salt having an anion represented by the formula (IA). wherein R1, A1, A13, X12, A14, R1A and R2A are defined in the specification.Type: GrantFiled: July 18, 2012Date of Patent: February 18, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Tatsuro Masuyama, Satoshi Yamaguchi
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Patent number: 8617791Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.Type: GrantFiled: September 13, 2012Date of Patent: December 31, 2013Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8574812Abstract: A resist composition of the invention includes: (A1) a resin having a structural unit represented by the formula (I), (A2) a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and (B) an acid generator represented by the formula (II), wherein R1, A1, R2, Q1, Q2, L1, ring W1, and Z+ are defined in the specification.Type: GrantFiled: February 24, 2012Date of Patent: November 5, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Satoshi Yamaguchi
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Patent number: 8557499Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes a compound (A) that when exposed to actinic rays or radiation, generates any of the acids of general formula (II) below and a resin (B) whose rate of dissolution into an alkali developer is increased by the action of an acid. (The characters used in general formula (I) have the meanings mentioned in the description.Type: GrantFiled: July 8, 2010Date of Patent: October 15, 2013Assignee: FUJIFILM CorporationInventors: Shuhei Yamaguchi, Akinori Shibuya, Shohei Kataoka
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Resist composition, method of forming resist pattern, compound and acid generator including the same
Patent number: 8541157Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under the action of acid and an acid-generator component (B) which generates acid upon exposure, wherein the acid-generator component (B) includes an acid generator (B1) composed of a compound having a base dissociable group within a cation moiety.Type: GrantFiled: September 25, 2009Date of Patent: September 24, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Sho Abe -
Patent number: 8501382Abstract: There are disclosed sulfonic acid precursor compositions, as are methods of using these compositions in, for example, photolithography. Other embodiments are also disclosed.Type: GrantFiled: February 19, 2010Date of Patent: August 6, 2013Assignee: The Research Foundation of State Univ. of New YorkInventor: Robert L. Brainard
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Patent number: 8460851Abstract: A salt represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents *—CO—O-La- or *—CH2—O-Lb-, * represents a binding position to —C(Q1)(Q2)-, La and Lb independently represent a C1-C15 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, ring W1 represents a C2-C36 nitrogen-containing heterocyclic group in which one or more —CH2— can be replaced by —O—, and Z1? represents an organic counter ion.Type: GrantFiled: January 6, 2011Date of Patent: June 11, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Koji Ichikawa
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Patent number: 8445176Abstract: A lithographic printing plate precursor comprising an image-recording layer, said image-recording layer being photopolymerizable upon exposure to light having a wavelength of from 300 to 500 nm and containing a mixture of sensitizers.Type: GrantFiled: May 15, 2008Date of Patent: May 21, 2013Assignee: Agfa Graphics NVInventors: Jan Venneman, Peter Hendrikx, Paul Callant, Alexander Williamson
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Patent number: 8435717Abstract: A sulfonic acid onium salt represented by the following formula (1) can be used as a superior radiosensitive acid generator for resist compositions. It is possible to form a good pattern by using a resist composition containing this sulfonic acid onium salt. In formula (1), R1 represents a monovalent organic group, and Q+ represents a sulfonium cation or iodonium cation.Type: GrantFiled: February 14, 2008Date of Patent: May 7, 2013Assignee: Central Glass Company, LimitedInventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
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Patent number: 8426113Abstract: The present invention provides chemically amplified silsesquioxane polymers for preparing masks using e-beam lithography. The silsesquioxane polymers have reactive sidechains that in the presence of an acid undergo acid catalyzed rearrangement to generate reactive functionalities that crosslink to form Si—O—Si bonds. The reactive side-chains comprise ?- and ?-substituted alkyl groups bound to the silicon of the silsesquioxane polymer. The substituent of the ?- and ?-substituted alkyl group is an electron withdrawing group. Resists generated with the chemically amplified silsesquioxane polymers of the present invention and imaged with e-beams have resolution of ?60 nm line/space.Type: GrantFiled: August 13, 2010Date of Patent: April 23, 2013Assignee: International Business Machines CorporationInventors: Luisa Dominica Bozano, Blake W. Davis, Alshakim Nelson, Jitendra Singh Rathore, Linda Karin Sundberg
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Patent number: 8426101Abstract: A photosensitive composition containing a compound having a specific structure as described in the specification, a pattern-forming method using the photosensitive composition and the compound having a specific structure used in the photosensitive composition.Type: GrantFiled: December 21, 2006Date of Patent: April 23, 2013Assignee: FUJIFILM CorporationInventors: Kenji Wada, Hiromi Kanda
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Patent number: 8372577Abstract: It is disclosed a photosensitive resin composition comprising (a) a binder polymer based on a copolymer containing benzyl (meth)acrylate as a building block, (b) a photopolymerizable compound having at least one polymerizable ethylenically unsaturated group in the molecule and (c) a photopolymerization initiator based on a hexarylbisimidazole compound, with a light-initiated color former being optionally contained as component (d). The composition has long-term keeping quality, exhibits particularly high resistance to plating and dry etching, as well as assuring improvement in resolution and adhesion; the composition may be used to form a photosensitive dry film.Type: GrantFiled: June 9, 2010Date of Patent: February 12, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yukihiko Tanaka, Shinkichi Asahi, Naoya Katsumata
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Patent number: 8361697Abstract: [Purpose] To provide a photosensitive resin composition having satisfactory compatibility during dry film formation, exhibiting similar sensitivity for exposure with both i-line radiation and h-line radiation type exposure devices, having excellent resolution and adhesiveness, allowing development with aqueous alkali solutions, and preferably, having no generation of aggregates during development. [Solution Means] A photosensitive resin composition comprising (a) 20-90 wt % of a thermoplastic copolymer having a specific copolymerizing component copolymerized, and having a carboxyl group content of 100-600 acid equivalents and a weight-average molecular weight of 5,000-500,000, (b) 5-75 wt % of an addition polymerizable monomer having at least one terminal ethylenic unsaturated group, (c) 0.01-30 wt % of a photopolymerization initiator containing a triarylimidazolyl dimer, and (d) 0.001-10 wt % of a pyrazoline compound.Type: GrantFiled: March 19, 2009Date of Patent: January 29, 2013Assignee: Asahi Kasei E-Materials CorporationInventor: Yosuke Hata
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Patent number: 8349533Abstract: A resist lower-layer composition configured to be used by a multi-layer resist method used in lithography to form a layer lower than a photoresist layer acting as a resist upper layer film. The resist lower-layer composition is insoluble or poorly-soluble in an alkaline developer after formation of the lower layer, and the resist lower-layer composition comprises, at least, a thermal acid generator for generating an acid by heating at a temperature of 100° C. or higher.Type: GrantFiled: October 20, 2009Date of Patent: January 8, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Jun Hatakeyama, Takeru Watanabe, Takeshi Kinsho
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Patent number: 8349535Abstract: According to one embodiment, an actinic ray-sensitive or radiation-sensitive resin composition includes (A) a resin containing the repeating units of formulae (I), (II) and (III) that when acted on by an acid, becomes soluble in an alkali developer, and (B) a compound that when irradiated with actinic rays or radiation, generates a fluorine-containing acid, wherein each of R1 independently represents a hydrogen atom or an optionally substituted methyl group, R2 represents a halogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group or an optionally substituted aralkyl group, and n is an integer of 0 to 5, provided that when n is 2 or greater, multiple R2s may be identical to or different from each other.Type: GrantFiled: September 30, 2010Date of Patent: January 8, 2013Assignee: FUJIFILM CorporationInventors: Kana Fujii, Takamitsu Tomiga, Toru Tsuchihashi, Kazuyoshi Mizutani, Jiro Yokoyama, Shinichi Sugiyama, Shuji Hirano, Toru Fujimori
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Patent number: 8334088Abstract: Linear or branched functionalized polycarbosilanes having an absorbance less than 3.0 ?m?1 at 193 nm and a relatively high refractive index are provided. The functionalized polycarbosilanes contain at least one pendant group that is acid labile or aqueous base soluble. Also disclosed are photoresists formulations containing the functionalized polycarbosilanes that are suitable for use in lithography, e.g., immersion lithography.Type: GrantFiled: November 3, 2010Date of Patent: December 18, 2012Assignee: International Business Machines CorporationInventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong
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Patent number: 8329377Abstract: An imide compound represented by the formula (I): wherein R1 represents a C1-C20 aliphatic hydrocarbon group etc., W1 represents —CO—O— etc., Q1 and Q2 each independently represent a fluorine atom etc., and A represents a group represented by the formula (I-1): wherein A1 represents —CH2—CH2— etc., and a chemically amplified resist composition containing the same.Type: GrantFiled: July 21, 2009Date of Patent: December 11, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Ichiki Takemoto, Tatsuro Masuyama, Takashi Hiraoka
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Patent number: 8273521Abstract: A radiation-sensitive resin composition includes a compound shown by a formula (1) in which R1 represents a divalent hydrocarbon group having 1 to 20 carbon atoms and R2 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, or R1 and R2 form a heterocyclic structure having 4 to 20 carbon atoms, R3 represents a monovalent acid-dissociable group, n is an integer from 1 to 6, each of R4A, R4B, and R4C represents one of an alkyl group having 1 to 4 carbon atoms and a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms, or R4A represents one of an alkyl group having 1 to 4 carbon atoms and a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms and R4B and R4C form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms.Type: GrantFiled: July 30, 2010Date of Patent: September 25, 2012Assignee: JSR CorporationInventors: Mitsuo Sato, Kazuo Nakahara, Hiromitsu Nakashima, Takanori Nakano, Makoto Sugiura
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Patent number: 8257905Abstract: A method of fabricating a thin film transistor substrate and a negative photoresist composition used therein are provided, which can reduce pattern inferiority. The method of fabricating a thin film transistor substrate includes forming a conductive film composed of a conductive material on a substrate, forming an etch pattern composed of a negative photoresist composition on the conductive film, and forming a conductive pattern by etching the conductive film using the etch pattern as an etching mask, wherein the negative photoresist composition includes 10-50 parts by weight of novolak resin including a hydroxyl group that is soluble in an alkali developing solution, 0.5-10 parts by weight of a first photo acid generator represented by the following formula (1), 0.Type: GrantFiled: January 11, 2010Date of Patent: September 4, 2012Assignee: Samsung Electronics Co., Ltd.Inventors: Yeong-Beom Lee, Hi-Kuk Lee, Byung-Uk Kim, Hyoc-Min Youn, Ki-Hyuk Koo
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Patent number: 8252507Abstract: A novel photoactive compound is provided. The photoactive compound has a structure represented by Formula 1: wherein R1, R2, R3, A, X, Y, n and m are as defined in the specification. The photoactive compound efficiently absorbs UV light. Accordingly, the photoactive compound has an improved ability to generate radicals and is efficiently photopolymerized with unsaturated bonds. Further provided is a photosensitive resin composition comprising the photoactive compound. The photosensitive resin composition has good sensitivity because it efficiently absorbs UV light. In addition, the photosensitive resin composition has excellent characteristics in terms of residual film ratio, mechanical strength and resistance to heat, chemicals and development. Therefore, the photosensitive resin composition is advantageously used in curing materials for column spacers, overcoats and passivation films of liquid crystal display devices.Type: GrantFiled: April 1, 2009Date of Patent: August 28, 2012Assignee: LG Chem, Ltd.Inventors: Chang Ho Cho, Sung Hyun Kim, Raisa Kharbash, Keon Woo Lee, Sang Kyu Kwak, Dong Kung Oh, Chang Soon Lee, Kyoung Hoon Min
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Patent number: 8211613Abstract: The present invention provides a radical generator having a naphthalimide structure or a crosslinking agent and a photosensitive compound having a function as a radical generator. A photoradical polymerization initiator of the present invention comprises a compound (a) having only one naphthalimide structure-containing group in one molecule. The radial generator of the present invention comprises a compound (c) having two or more naphthalimide structure-containing groups in one molecule and also functions as a crosslinking agent. A first photosensitive compound of the present invention comprises a compound (d) having a naphthalimide structure-containing group and an ethylenic unsaturated group in one molecule. A second photosensitive compound of the present invention comprises a polymer (e) of one or more radical polymerizable compounds containing the compound (d).Type: GrantFiled: July 2, 2008Date of Patent: July 3, 2012Assignee: Dai Nippon Printing Co., Ltd.Inventor: Katsuya Sakayori
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Patent number: 8206890Abstract: A resist composition including: a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid; and an acid-generator component (B) which generates acid upon exposure, wherein said acid-generator component (B) comprises an acid generator (B1) including a compound represented by general formula (b1-11) shown below: wherein R7? to R9? each independently represent an aryl group or an alkyl group, wherein two of R7? to R9? may be bonded to each other to form a ring with the sulfur atom, and at least one of R7? to R9? represents a substituted aryl group having a group represented by general formula (I) shown below as a substituent; X? represents an anion; and Rf represents a fluorinated alkyl group.Type: GrantFiled: July 8, 2009Date of Patent: June 26, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehiro Seshimo, Tsuyoshi Nakamura, Naoto Motoike, Hiroaki Shimizu, Kensuke Matsuzawa, Hideo Hada
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Patent number: 8206886Abstract: A photosensitive composition comprises (A) a sulfonium or iodonium salt having an anion represented by one of formulae (I) and (II): wherein Y represents an alkylene group substituted with at least one fluorine atom, and R represents an alkyl group or a cycloalkyl group.Type: GrantFiled: January 25, 2005Date of Patent: June 26, 2012Assignee: FUJIFILM CorporationInventor: Kunihiko Kodama
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Patent number: 8198008Abstract: A photosensitive resin composition comprising: (A) a binder polymer; (B) a photopolymerizable compound that has an ethylenically unsaturated bond; and (C1) a compound represented by general formula (1) below, wherein, at least one R represents a C1-10 alkoxy group or a C1-12 alkyl group; the sum of a, b, and c is 1 to 6; and when the sum of a, b, and c is 2 to 6, each R may be the same as or different from one another.Type: GrantFiled: July 16, 2010Date of Patent: June 12, 2012Assignee: Hitachi Chemical Company, Ltd.Inventors: Masahiro Miyasaka, Takashi Kumaki