Nitrogen In Heterocyclic Ring Patents (Class 430/920)
  • Patent number: 11919997
    Abstract: 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: Grant
    Filed: May 25, 2021
    Date of Patent: March 5, 2024
    Assignee: eChem Solutions Corp.
    Inventors: Meng-Po Liu, Yu-Chun Chen
  • Patent number: 11762288
    Abstract: A resist composition that generates an acid upon exposure and whose solubility in a developing solution is changed by action of an acid.
    Type: Grant
    Filed: December 10, 2020
    Date of Patent: September 19, 2023
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroto Yamazaki, Seiji Todoroki, Masahiro Shiosaki, Nobuhiro Michibayashi
  • Patent number: 11567409
    Abstract: 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: Grant
    Filed: April 17, 2020
    Date of Patent: January 31, 2023
    Assignee: 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
  • Patent number: 9029070
    Abstract: 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: Grant
    Filed: November 2, 2012
    Date of Patent: May 12, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito
  • Patent number: 9023585
    Abstract: 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: Grant
    Filed: June 20, 2013
    Date of Patent: May 5, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito, Hiroaki Shimizu
  • Patent number: 9023581
    Abstract: 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: Grant
    Filed: June 14, 2011
    Date of Patent: May 5, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Akiya Kawaue, Kazushige Dohtani, Yoshiyuki Utsumi, Jun Iwashita, Kenri Konno, Daiju Shiono, Daichi Takaki
  • Patent number: 8956806
    Abstract: 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: Grant
    Filed: September 18, 2009
    Date of Patent: February 17, 2015
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Chien-Wei Wang, Ching-Yu Chang, Burn Jeng Lin
  • Patent number: 8932797
    Abstract: 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: Grant
    Filed: November 30, 2011
    Date of Patent: January 13, 2015
    Assignees: Dow Global Technologies LLC, Rohm and Haas Electronic Materials LLC
    Inventors: James W. Thackeray, Suzanne M. Coley, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour, Owendi Ongayi, Vipul Jain
  • Patent number: 8921028
    Abstract: 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: Grant
    Filed: March 7, 2012
    Date of Patent: December 30, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamaguchi, Koji Ichikawa
  • Patent number: 8906591
    Abstract: 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: Grant
    Filed: September 14, 2012
    Date of Patent: December 9, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8883395
    Abstract: 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: Grant
    Filed: September 14, 2012
    Date of Patent: November 11, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8871429
    Abstract: 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: Grant
    Filed: September 14, 2012
    Date of Patent: October 28, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8852846
    Abstract: 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: Grant
    Filed: April 4, 2012
    Date of Patent: October 7, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukako Anryu, Koji Ichikawa
  • Patent number: 8846301
    Abstract: 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: Grant
    Filed: May 21, 2009
    Date of Patent: September 30, 2014
    Assignee: Cornell University
    Inventors: Christopher K. Ober, George Malliaras, Jin-Kyun Lee, Alexander Zakhidov, Margarita Chatzichristidi, Priscilla Taylor
  • Patent number: 8846291
    Abstract: 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: Grant
    Filed: December 6, 2011
    Date of Patent: September 30, 2014
    Assignee: Tokyo Ohka Kogyo Co. Ltd.
    Inventors: Yoshiyuki Utsumi, Kenichiro Miyashita, Akiya Kawaue
  • Patent number: 8846296
    Abstract: 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: Grant
    Filed: May 2, 2012
    Date of Patent: September 30, 2014
    Assignee: International Business Machines Corporation
    Inventors: Kuang-Jung Chen, Wu-Song Huang, Ranee Wai-Ling Kwong, Sen Liu, Pushkara R. Varanasi
  • Patent number: 8835095
    Abstract: 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: Grant
    Filed: February 24, 2012
    Date of Patent: September 16, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Yuichi Mukai
  • Patent number: 8735047
    Abstract: 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: Grant
    Filed: July 18, 2012
    Date of Patent: May 27, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi
  • Patent number: 8709700
    Abstract: 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: Grant
    Filed: September 13, 2012
    Date of Patent: April 29, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8703384
    Abstract: 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: Grant
    Filed: November 23, 2011
    Date of Patent: April 22, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Kobayashi, Eiji Fukuda, Takayuki Nagasawa, Ryosuke Taniguchi, Youichi Ohsawa, Masayoshi Sagehashi, Yoshio Kawai
  • Patent number: 8697332
    Abstract: 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: Grant
    Filed: March 26, 2010
    Date of Patent: April 15, 2014
    Assignee: Dai Nippon Printing Co., Ltd.
    Inventors: Mami Katayama, Shunji Fukuda, Katsuya Sakayori, Kouji Kawaguchi
  • Patent number: 8663899
    Abstract: 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: Grant
    Filed: July 18, 2012
    Date of Patent: March 4, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takashi Hiraoka, Hiromu Sakamoto
  • Patent number: 8663901
    Abstract: 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: Grant
    Filed: September 13, 2012
    Date of Patent: March 4, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8652753
    Abstract: 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: Grant
    Filed: July 18, 2012
    Date of Patent: February 18, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Tatsuro Masuyama, Satoshi Yamaguchi
  • Patent number: 8617791
    Abstract: 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: Grant
    Filed: September 13, 2012
    Date of Patent: December 31, 2013
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8574812
    Abstract: 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: Grant
    Filed: February 24, 2012
    Date of Patent: November 5, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi
  • Patent number: 8557499
    Abstract: 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: Grant
    Filed: July 8, 2010
    Date of Patent: October 15, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Shuhei Yamaguchi, Akinori Shibuya, Shohei Kataoka
  • Patent number: 8541157
    Abstract: 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: Grant
    Filed: September 25, 2009
    Date of Patent: September 24, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Sho Abe
  • Patent number: 8501382
    Abstract: There are disclosed sulfonic acid precursor compositions, as are methods of using these compositions in, for example, photolithography. Other embodiments are also disclosed.
    Type: Grant
    Filed: February 19, 2010
    Date of Patent: August 6, 2013
    Assignee: The Research Foundation of State Univ. of New York
    Inventor: Robert L. Brainard
  • Patent number: 8460851
    Abstract: 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: Grant
    Filed: January 6, 2011
    Date of Patent: June 11, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamaguchi, Koji Ichikawa
  • Patent number: 8445176
    Abstract: 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: Grant
    Filed: May 15, 2008
    Date of Patent: May 21, 2013
    Assignee: Agfa Graphics NV
    Inventors: Jan Venneman, Peter Hendrikx, Paul Callant, Alexander Williamson
  • Patent number: 8435717
    Abstract: 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: Grant
    Filed: February 14, 2008
    Date of Patent: May 7, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
  • Patent number: 8426113
    Abstract: 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: Grant
    Filed: August 13, 2010
    Date of Patent: April 23, 2013
    Assignee: International Business Machines Corporation
    Inventors: Luisa Dominica Bozano, Blake W. Davis, Alshakim Nelson, Jitendra Singh Rathore, Linda Karin Sundberg
  • Patent number: 8426101
    Abstract: 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: Grant
    Filed: December 21, 2006
    Date of Patent: April 23, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Kenji Wada, Hiromi Kanda
  • Patent number: 8372577
    Abstract: 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: Grant
    Filed: June 9, 2010
    Date of Patent: February 12, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yukihiko Tanaka, Shinkichi Asahi, Naoya Katsumata
  • Patent number: 8361697
    Abstract: [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: Grant
    Filed: March 19, 2009
    Date of Patent: January 29, 2013
    Assignee: Asahi Kasei E-Materials Corporation
    Inventor: Yosuke Hata
  • Patent number: 8349533
    Abstract: 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: Grant
    Filed: October 20, 2009
    Date of Patent: January 8, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Jun Hatakeyama, Takeru Watanabe, Takeshi Kinsho
  • Patent number: 8349535
    Abstract: 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: Grant
    Filed: September 30, 2010
    Date of Patent: January 8, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Kana Fujii, Takamitsu Tomiga, Toru Tsuchihashi, Kazuyoshi Mizutani, Jiro Yokoyama, Shinichi Sugiyama, Shuji Hirano, Toru Fujimori
  • Patent number: 8334088
    Abstract: 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: Grant
    Filed: November 3, 2010
    Date of Patent: December 18, 2012
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 8329377
    Abstract: 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: Grant
    Filed: July 21, 2009
    Date of Patent: December 11, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ichiki Takemoto, Tatsuro Masuyama, Takashi Hiraoka
  • Patent number: 8273521
    Abstract: 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: Grant
    Filed: July 30, 2010
    Date of Patent: September 25, 2012
    Assignee: JSR Corporation
    Inventors: Mitsuo Sato, Kazuo Nakahara, Hiromitsu Nakashima, Takanori Nakano, Makoto Sugiura
  • Patent number: 8257905
    Abstract: 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: Grant
    Filed: January 11, 2010
    Date of Patent: September 4, 2012
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Yeong-Beom Lee, Hi-Kuk Lee, Byung-Uk Kim, Hyoc-Min Youn, Ki-Hyuk Koo
  • Patent number: 8252507
    Abstract: 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: Grant
    Filed: April 1, 2009
    Date of Patent: August 28, 2012
    Assignee: 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
  • Patent number: 8211613
    Abstract: 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: Grant
    Filed: July 2, 2008
    Date of Patent: July 3, 2012
    Assignee: Dai Nippon Printing Co., Ltd.
    Inventor: Katsuya Sakayori
  • Patent number: 8206886
    Abstract: 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: Grant
    Filed: January 25, 2005
    Date of Patent: June 26, 2012
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 8206890
    Abstract: 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: Grant
    Filed: July 8, 2009
    Date of Patent: June 26, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehiro Seshimo, Tsuyoshi Nakamura, Naoto Motoike, Hiroaki Shimizu, Kensuke Matsuzawa, Hideo Hada
  • Patent number: 8198008
    Abstract: 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: Grant
    Filed: July 16, 2010
    Date of Patent: June 12, 2012
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Masahiro Miyasaka, Takashi Kumaki
  • Patent number: 8192916
    Abstract: 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: Grant
    Filed: July 16, 2010
    Date of Patent: June 5, 2012
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Masahiro Miyasaka, Takashi Kumaki
  • Patent number: 8182979
    Abstract: A photopolymerization initiator is provided. The photopolymerization initiator contains at least one unsaturated double bond and at least one oxime ester group in the molecule. The photopolymerization initiator comprises a compound represented by Formula 1 or 2: wherein R1 and R2 are each independently —CH3, —C2H5, —C3H7 or —C6H5; wherein R3, R4 and R5 are each independently —CH3, —C2H5, —C3H7 or —C6H5. Further provided is a photosensitive resin composition comprising the photopolymerization initiator. The use of the photosensitive resin composition in photolithography reduces the formation of volatile residue during post-development baking.
    Type: Grant
    Filed: October 30, 2009
    Date of Patent: May 22, 2012
    Assignee: LG Chem, Ltd.
    Inventors: Keon Woo Lee, Raisa Kharbash, Chang Ho Cho, Sung Hyun Kim, Sang Kyu Kwak, Dong Kung Oh, Chang Soon Lee
  • Patent number: 8148044
    Abstract: A positive photosensitive composition includes at least one compound that when exposed to actinic rays or radiation, generates any of the sulfonic acids of general formula (I) and a resin whose solubility in an alkali developer is increased by the action of an acid, wherein each of X1 and X2 independently represents a fluorine atom or a fluoroalkyl group, R1 represents a group with a polycyclic structure, provided that the polycyclic structure may have a substituent, and R2 represents a hydrogen atom, a chain alkyl group, a monocyclic alkyl group, a group with a polycyclic structure or a monocyclic aryl group, provided that each of the chain alkyl group, monocyclic alkyl group, polycyclic structure and monocyclic aryl group may have a substituent, and provided that R1 and R2 may be bonded to each other to thereby form a polycyclic structure.
    Type: Grant
    Filed: October 29, 2009
    Date of Patent: April 3, 2012
    Assignee: Fujifilm Corporation
    Inventors: Shuhei Yamaguchi, Tomotaka Tsuchimura, Yuko Tada