Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
  • Patent number: 8628908
    Abstract: A chemically amplified resist composition is provided comprising (A) a specific tertiary amine compound, (B) a specific acid generator, (C) a base resin having an acidic functional group protected with an acid labile group, which is substantially insoluble in alkaline developer and turns soluble in alkaline developer upon deprotection of the acid labile group, and (D) an organic solvent. The resist composition has a high resolution, improved defect control in the immersion lithography, and good shelf stability.
    Type: Grant
    Filed: February 28, 2012
    Date of Patent: January 14, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Tomohiro Kobayashi, Masayoshi Sagehashi, Takeshi Nagata, Youichi Ohsawa, Ryosuke Taniguchi
  • Patent number: 8628911
    Abstract: Provided are polymers and photoresist compositions useful in forming photolithographic patterns. Also provided are substrates coated with the photoresist compositions and methods of forming photolithographic patterns. The compositions, methods and coated substrates find particular applicability in the manufacture of semiconductor devices.
    Type: Grant
    Filed: December 2, 2011
    Date of Patent: January 14, 2014
    Assignees: Rohm and Haas Electronic Materials LLC, Dow Global Technologies LLC
    Inventors: Young Cheol Bae, David Richard Wilson, Jibin Sun
  • Patent number: 8617785
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes: (A) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (B) a resin capable of increasing a dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure; and (D) a low molecular compound having a group capable of leaving by an action of an acid, and a pattern forming method uses the composition.
    Type: Grant
    Filed: January 15, 2010
    Date of Patent: December 31, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Shuhei Yamaguchi
  • Patent number: 8614283
    Abstract: To provide a resist polymer comprising, as a structural unit, an acid-decomposable unit having a structure represented by formula (1) or (2) which exhibits a small line edge roughness and produces little defects in DUV excimer laser lithography or the like.
    Type: Grant
    Filed: February 22, 2011
    Date of Patent: December 24, 2013
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Hikaru Momose, Atsushi Ootake, Tadashi Nakamura, Akifumi Ueda
  • Patent number: 8609317
    Abstract: A salt represented by the formula (I—Pb): wherein Xpb represents a single bond or —O—, Rpb represents a single bond etc., Ypb represents a polymerizable group, Zpb represents an organic group, Xpc represents a single bond or a C1-C4 alkylene group, and Rpc represents a C1-C10 aliphatic hydrocarbon group which can have one or more substituents etc.
    Type: Grant
    Filed: July 9, 2010
    Date of Patent: December 17, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Yuko Yamashita
  • Patent number: 8609321
    Abstract: A radiation-sensitive resin composition includes a polymer having a structural unit represented by a formula (I). In the formula (I), R1 represents a hydrogen atom or a methyl group. X represents a bivalent alicyclic hydrocarbon group not having or having a substituent. Y represents a bivalent hydrocarbon group having 1 to 20 carbon atoms. R2 represents a methyl group or a trifluoromethyl group.
    Type: Grant
    Filed: March 8, 2013
    Date of Patent: December 17, 2013
    Assignee: JSP Corporation
    Inventors: Hiromitsu Nakashima, Reiko Kimura, Kazuo Nakahara, Mitsuo Sato
  • Patent number: 8597870
    Abstract: A coating material for use during a lithography process. In an example, a coating material disposed on a material layer includes a polymer and a quencher catcher chemically bonded to the polymer. The quencher catcher substantially neutralizes any quencher that diffuses into the coating material from the material layer.
    Type: Grant
    Filed: June 18, 2012
    Date of Patent: December 3, 2013
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventor: Ching-Yu Chang
  • Patent number: 8592128
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes: (A) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (B) a resin capable of increasing a dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure; and (D) a low molecular compound having a group capable of leaving by an action of an acid, and a pattern forming method uses the composition.
    Type: Grant
    Filed: January 15, 2010
    Date of Patent: November 26, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Shuhei Yamaguchi
  • Patent number: 8592132
    Abstract: A resist composition 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 having an acid-labile group. wherein R1 represents a hydrogen atom or a methyl group; A1 represents a C1 to C6 alkanediyl group; R2 represents a C1 to C10 hydrocarbon group having a fluorine atom.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: November 26, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi, Yuki Suzuki
  • Patent number: 8592622
    Abstract: A polymerizable fluorine-containing compound represented by formula (1), wherein R1 represents a polymerizable double-bond containing group, R2 represents an acid-labile protecting group, R3 represents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein R2, R3 and W are defined as above, each of R4, R5 and R6 independently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R4, R5 and R6 may be combined to form a ring. This polymer compound can provide a resist composition capable of forming a pattern that is transparent to exposure light and superior in rectangularity.
    Type: Grant
    Filed: January 4, 2011
    Date of Patent: November 26, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka
  • Patent number: 8592131
    Abstract: An ortho-nitrobenzyl ester compound including a compound represented by Chemical Formula 1, and a positive photosensitive resin composition including the same are provided.
    Type: Grant
    Filed: September 22, 2011
    Date of Patent: November 26, 2013
    Assignee: Cheil Industries Inc.
    Inventors: Min-Kook Chung, Ji-Young Jeong, Hyun-Yong Cho, Yong-Sik Yoo, Jeong-Woo Lee, Jong-Hwa Lee, Hwan-Sung Cheon, Soo-Young Kim, Young-Ho Kim, Jae-Hyun Kim, Su-Min Park
  • Patent number: 8586366
    Abstract: Gel for radiation dosimeter including a gel part (A) and a gel part (B) that become cloudy when exposed to a fixed dose or more, wherein said gel part (A) exposed to more than a specified dose above the fixed dose maintains a cloudy state regardless of the decrease in external temperature; and said gel part (B) exposed to less than the specified dose above the fixed dose changes gradually from a cloudy state into a transparent state according to the decrease in external temperature.
    Type: Grant
    Filed: June 15, 2011
    Date of Patent: November 19, 2013
    Assignee: Japan Atomic Energy Agency
    Inventors: Akihiro Hiroki, Naotsugu Nagasawa, Masao Tamada, Takuji Kojima, Yuichi Sato, Akio Ohta, Hisamichi Yamabayashi, Takayoshi Yamamoto
  • Patent number: 8580481
    Abstract: The resist polymer of the present invention comprises a specific constitutional unit having a cyano group, a constitutional unit having an acid-dissociable group, and a specific constitutional unit having a lactone skeleton. When the above polymer is used as a resist resin in DUV excimer laser lithography or electron beam lithography, it exhibits high sensitivity and high resolution, and provides a good resist pattern shape, having a small degree of occurrence of line edge roughness or generation of microgels.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: November 12, 2013
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Hikaru Momose, Atsushi Ootake, Akifumi Ueda, Tadayuki Fujiwara, Masaru Takeshita, Ryotaro Hayashi, Takeshi Iwai
  • Patent number: 8580486
    Abstract: There is provided an acid having a fluorine-containing carbanion structure or a salt having a fluorine-containing carbanion structure, which is represented by the following general formula (1). By using a photoacid generator for chemically amplified resist materials that generates this acid, it is possible to provide a photoacid generator which has a high sensitivity to the ArF excimer laser light or the like, of which acid (photo generated acid) to be generated has a sufficiently high acidity, and which has a high dissolution in resist solvent and a superior compatibility with resin, and a resist material containing such a photoacid generator.
    Type: Grant
    Filed: March 10, 2009
    Date of Patent: November 12, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Masashi Nagamori, Satoru Narizuka, Susumu Inoue, Takashi Kume
  • Patent number: 8574816
    Abstract: The invention provides a positive resist composition comprising, as base resins contained therein, (A) a polymer having a weight-average molecular weight of 1000 to 500000 and containing a repeating unit which contains a structure having a hydrogen atom of a carboxyl group thereof substituted with an acid-labile group having a cyclic structure and (B) a novolak resin of a substituted or an unsubstituted naphtholphthalein, and in addition, a photo acid generator. There can be provided a positive resist composition having an appropriate absorption to form a pattern on a highly reflective substrate, excellent characteristics in adhesion and implantation onto a non-planar substrate, a good pattern profile after light exposure, and an ion implantation resistance at the time of ion implantation; and a patterning process.
    Type: Grant
    Filed: August 13, 2012
    Date of Patent: November 5, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Daisuke Kori
  • 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: 8574813
    Abstract: A resist composition for immersion exposure and a method of forming a resist pattern which can satisfy both of excellent resistance to an immersion medium and lithography properties. The resist composition for immersion exposure includes a resin component (A) which exhibits changed alkali solubility under action of acid and an acid-generator component (B) which generates acid upon irradiation, the resin component (A) including a resin (A1) which contains a fluorine atom and a resin (A2) which has a structural unit (a?) derived from acrylic acid and contains no fluorine atom, and the amount of the resin (A1) contained in the resin component (A) being within the range from 0.1 to 50% by weight.
    Type: Grant
    Filed: May 10, 2012
    Date of Patent: November 5, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Makiko Irie
  • Patent number: 8574817
    Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1), (2) or (3) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a reduced acid diffusion rate, and forms a pattern with good profile, minimal edge roughness, and etch resistance. In formula (1), R1, R2, R5, R6, R8, and R9 are alkyl, aryl, or alkenyl, R3, R4, R7, R10, and R11 are hydrogen, alkyl, alkoxy, acyloxy, halogen, cyano, nitro, hydroxyl or trifluoromethyl, M is methylene or ethylene, R is a single bond or linking group.
    Type: Grant
    Filed: September 13, 2012
    Date of Patent: November 5, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8574811
    Abstract: A resist composition contains; a resin having a structural unit derived from a compound represented by the formula (a); and an acid generator. wherein R1 represents a hydrogen atom or a methyl group; R2 represents an optionally substituted C1 to C18 aliphatic hydrocarbon group; A1 represents an optionally substituted C1 to C6 alkanediyl group or a group represented by the formula (a-g1); wherein s represents 0 or 1; A10 and A12 independently represent an optionally substituted C1 to C5 aliphatic hydrocarbon group; A11 represents a single bond or an optionally substituted C1 to C5 aliphatic hydrocarbon group; X10 and X11 independently represents an oxygen atom, a carbonyl group, a carbonyloxy group or an oxycarbonyl group; provided that a total number of the carbon atom of A10, A11, A12, X10 and X11 is 6 or less.
    Type: Grant
    Filed: August 30, 2011
    Date of Patent: November 5, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Satoshi Yamamoto, Koji Ichikawa
  • Patent number: 8568956
    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) a compound represented by the formula (II), wherein R1 represents a hydrogen atom or a methyl group; A1 represents a C1 to C6 alkanediyl group; R2 represents a C1 to C10 hydrocarbon group having a fluorine atom; ring W1 represents a C2 to C36 substituted heterocyclic ring; R3 represents a C1 to C30 hydrocarbon group, and one or more —CH2— contained in the hydrocarbon group may be replaced by —O— or —CO—.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: October 29, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi
  • Patent number: 8563218
    Abstract: A resist composition of the present invention has (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) a compound represented by the formula (II). wherein R1 represents a hydrogen atom or a methyl group; A1 represents a C1 to C6 alkanediyl group; R2 represents a C1 to C10 hydrocarbon group having a fluorine atom, R3 and R4 in each occurrence independently represent a C1 to C12 hydrocarbon group, a C1 to C6 alkoxyl group, a C2 to C7 acyl group, a C2 to C7 acyloxy group, a C2 to C7 alkoxycarbonyl group, a nitro group or a halogen atom; m? and n? independently represent an integer of 0 to 4.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: October 22, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takahiro Yasue
  • Patent number: 8563217
    Abstract: A resist composition having; (A1) a resin having a structural unit represented by the formula (I), (A2) a resin having a structural unit represented by the formula (II) and 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, wherein R1, A1, R2, R3, and ring X1 are defined in the specification.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: October 22, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Akira Kamabuchi
  • Patent number: 8563219
    Abstract: A resist composition containing; (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) a salt having an anion represented by the formula (IA), wherein R1, A1, R2, R1A and R2A are defined in the specification.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: October 22, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Tatsuro Masuyama, Satoshi Yamaguchi
  • Patent number: 8551684
    Abstract: A polymer for forming a resist protection film which is used in a liquid immersion lithography process to protect a photoresist layer, a composition for forming a resist protection film, and a method of forming a pattern of a semiconductor device using the composition are disclosed. The polymer for forming a resist protection film includes a repeating unit represented by Formula 1 below. In Formula 1, R1 is a hydrogen atom (H), a fluorine atom (F), a methyl group (—CH3), a C1-C20 fluoroalkyl group, or a C1-C5 hydroxyalkyl group, R2 is a C1-C10 linear or branched alkylene group or alkylidene group, or a C5-C10 cycloalkylene group or cycloalkylidene group, X is wherein n is an integer of 0 to 5 and * denotes the remaining moiety of Formula 1 after excluding X, and m, the stoichiometric coefficient of X, is 1 or 2.
    Type: Grant
    Filed: June 30, 2011
    Date of Patent: October 8, 2013
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jong Kyoung Park, Man Ho Han, Hyun Jin Kim, Deog Bae Kim
  • Patent number: 8546060
    Abstract: A chemically amplified positive resist composition is provided comprising a polymer PB having an amine structure bound thereto and a polymer PA comprising recurring units having an acidic side chain protected with an acid labile protective group and recurring units having an acid generating moiety on a side chain.
    Type: Grant
    Filed: February 15, 2011
    Date of Patent: October 1, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Keiichi Masunaga, Satoshi Watanabe, Akinobu Tanaka, Daisuke Domon
  • 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: 8541158
    Abstract: A positive resist composition is provided comprising an acid generator, a resin component which generates resin-solubilizing groups under the action of acid so that the resin component becomes soluble in an alkaline developer, at least some resin-solubilizing groups being carboxyl groups, and a compound for activating or condensing a carboxyl group. When processed by the lithography, the resist composition forms a resist pattern having a very high resolution and good mask fidelity.
    Type: Grant
    Filed: January 25, 2011
    Date of Patent: September 24, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Wataru Kusaki, Takeshi Kinsho, Takeru Watanabe
  • Patent number: 8541161
    Abstract: Provided are an actinic ray-sensitive or radiation-sensitive resin composition; a resist film using the composition; and a pattern forming method. The actinic ray-sensitive or radiation-sensitive resin composition includes (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, the resin containing a repeating unit represented by formula (I), a repeating unit represented by formula (II) and a repeating unit represented by formula (III), and (B) a compound capable of generating a fluorine atom-containing acid upon irradiation with an actinic ray or radiation: wherein each of R1 and R11 independently represents a hydrogen atom or an alkyl group which may have a substituent, and R12 represents a phenyl group which may have a substituent.
    Type: Grant
    Filed: March 23, 2010
    Date of Patent: September 24, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Kana Fujii, Shuji Hirano, Shinki Yamada, Toru Fujimori
  • Patent number: 8535871
    Abstract: A radiation-sensitive resin composition includes a first polymer that includes a repeating unit having an acid-labile group and becomes alkali-soluble upon dissociation of the acid-labile group, and a radiation-sensitive acid-generating agent. The acid-labile group has a structure shown by a general formula (1). R1 represents a methyl group or the like, R2 represents a hydrocarbon group that forms a cyclic structure, R3 represents a fluorine atom or the like, R4 represents a carbon atom, and n1 is an integer from 1 to 7.
    Type: Grant
    Filed: December 14, 2011
    Date of Patent: September 17, 2013
    Assignee: JSR Corporation
    Inventors: Yuusuke Asano, Takanori Kawakami
  • Patent number: 8535868
    Abstract: A positive resist composition including a resin component (A1) having a structural unit (a1) derived from an acrylate ester which may have an atom other than hydrogen or a group bonded to the carbon atom on the ? position and containing an acid dissociable, dissolution inhibiting group, and a structural unit (a0) containing an —SO2— containing cyclic group; a compound (C1) represented by general formula (c1) shown below; and an acid-generator component (B) which generates acid upon exposure, wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Y1 represents a divalent aliphatic hydrocarbon group; R1 represents a hydrogen atom, a fluorine atom, an alkyl group or a fluorinated alkyl group; p represents an integer of 1 to 10; and A+ represents an organic cation.
    Type: Grant
    Filed: July 6, 2011
    Date of Patent: September 17, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Yoshiyuki Utsumi
  • Patent number: 8535872
    Abstract: An etch resistant thermally curable Underlayer composition for use in a multiplayer lithographic process for producing a photolithographic bilayer coated substrate, the composition being a composition of: (a) a polymer comprising repeating units of Structure I, II and III (b) at least one crosslinking agent; (c) at least one thermal acid generator; and (d) at least one solvent.
    Type: Grant
    Filed: March 21, 2012
    Date of Patent: September 17, 2013
    Assignee: Fujifilm Electronic Materials, U.S.A., Inc.
    Inventors: Binod B. De, Ognian N. Dimov, Stephanie J. Dilocker
  • Patent number: 8530139
    Abstract: Disclosed is a solvent for printing which comprises a first solvent selected from the group consisting of acetone, methyl ethyl ketone, methyl acetate, ethyl acetate, methanol and mixtures thereof, and a second solvent selected from the group consisting of propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monomethyl ether (PGME), isopropanol, butyl acetate, ethyl-3-ethoxypropionate and mixtures thereof. Further disclosed are a pattern composition for printing comprising the solvent for printing, and a patterning method using the composition. The use of the solvent for printing enables formation of an accurate pattern.
    Type: Grant
    Filed: March 19, 2012
    Date of Patent: September 10, 2013
    Assignee: LG Display Co., Ltd.
    Inventors: Hong Suk Yoo, Chul Ho Kim, Jung Jae Lee, Tae Young Oh
  • Patent number: 8518629
    Abstract: A resist composition for immersion exposure, including a base component (A) that exhibits changed solubility in an alkali developing solution under action of acid, an acid generator component (B) that generates acid upon exposure, and a fluorine-containing compound (C) represented by general formula (c-1) (in formula (c-1), R1 represents an organic group which may contain a polymerizable group; X represents a divalent organic group having an acid dissociable portion; and R2 represents an organic group having a fluorine atom).
    Type: Grant
    Filed: August 26, 2011
    Date of Patent: August 27, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tsuyoshi Kurosawa, Hiroaki Shimizu
  • Patent number: 8518628
    Abstract: A material is provided for use in an immersion lithographic process of a semiconductor substrate. The material includes a photo-sensitive polymer configured to turn soluble to a base solution in response to reaction with an acid and at least one of either a base soluble polymer or an acid labile polymer. The base soluble polymer is configured to turn soluble to water in response to reaction with a developer solution. The acid labile polymer is configured to turn soluble to water after releasing a leaving group in reaction to the acid.
    Type: Grant
    Filed: September 22, 2006
    Date of Patent: August 27, 2013
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Ching-Yu Chang, Chih-Cheng Chiu
  • Patent number: 8507172
    Abstract: A positive resist composition comprises: (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (B) a resin of which solubility in an alkali developer increases under action of an acid; and (C) a compound capable of decomposing under action of an acid to generate an acid.
    Type: Grant
    Filed: January 28, 2008
    Date of Patent: August 13, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Kenji Wada
  • Patent number: 8507177
    Abstract: A material for use in lithography processing includes a polymer that turns soluble to a base solution in response to reaction with acid and a plurality of magnetically amplified generators (MAGs) each having a magnetic element and each decomposing to form acid bonded with the magnetic element in response to radiation energy.
    Type: Grant
    Filed: March 17, 2011
    Date of Patent: August 13, 2013
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Hsien-Cheng Wang, Chin-Hsiang Lin, Heng-Jen Lee, Ching-Yu Chang, Hua-Tai Lin, Burn Jeng Lin
  • Patent number: 8507176
    Abstract: Provided are radiation-sensitive polymers and compositions which may be used in photolithographic processes. The polymers and compositions provide enhanced sensitivity to activating radiation.
    Type: Grant
    Filed: December 30, 2010
    Date of Patent: August 13, 2013
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: James W. Thackeray, Emad Aqad
  • Patent number: 8501384
    Abstract: A positive resist composition comprising a polymer having a tetrahydrobenzocycloheptane-substituted secondary or tertiary carboxyl group ester as an acid labile group exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal edge roughness after exposure, a significant effect of suppressing acid diffusion rate, and improved etching resistance.
    Type: Grant
    Filed: January 7, 2011
    Date of Patent: August 6, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takeru Watanabe, Seiichiro Tachibana
  • Patent number: 8486605
    Abstract: A positive resist composition including: a base material component (A) which exhibits increased solubility in an alkali developing solution under the action of acid; and an acid generator component (B) which generates acid upon exposure; dissolved in an organic solvent (S), wherein the base material component (A) includes a resin component (A1) having 4 types of specific structural units, and the organic solvent (S) includes from 60 to 99% by weight of an alcohol-based organic solvent (S1) and from 1 to 40% by weight of at least one organic solvent (S2) selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether and cyclohexanone.
    Type: Grant
    Filed: January 21, 2010
    Date of Patent: July 16, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Yasuhiro Yoshii, Jiro Yokoya, Hirokuni Saito, Tsuyoshi Nakamura
  • Patent number: 8486606
    Abstract: An acrylate derivative represented by the following general formula (1): (in the formula, R1 represents a hydrogen atom, a methyl group or a trifluoromethyl group; each of R2, R3, R5, R7, R8, R9 and R10 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkoxy group; each of R4 and R6 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkoxy group, or R4 and R6 are bonded to each other to represent an alkylene group, —O— or —S—; n represents 0, 1 or 2; and W represents an alkylene group or a cycloalkylene group); an intermediate thereof; a method for producing the same; a polymer compound which is obtainable from polymerization of a raw material containing the foregoing acrylate derivative and which is excellent in solubility in an organic solvent used for the preparation of a photoresist composition; and a photoresist composition containing the polymer compound, an organic solvent and a photo acid generator and having excellent adhesion to s
    Type: Grant
    Filed: June 30, 2009
    Date of Patent: July 16, 2013
    Assignee: Kuraray Co., Ltd.
    Inventors: Junko Sato, Osamu Nakayama, Takashi Fukumoto
  • Patent number: 8481243
    Abstract: The present invention provides a resin comprising a structural unit represented by the formula (aa): wherein R1 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a hydrogen atom or a halogen atom, T1 represents a C4-C34 sultone ring group optionally having one or more substituents, Z1 represents a C1-C6 alkanediyl group optionally having one or more substituents, or a group represented by the formula (a-1): -A10X10-A11sX11-A12-??(a-1) wherein X10 and X11 each independently represents —O—, —NH—, —CO—, —CO—O—, —O—CO—, —CO—NH— or —NH—CO—, A10, A11 and A12 each independently represent a C1-C5 divalent aliphatic hydrocarbon group optionally having one or more substituents, and s represents 0 or 1, and Z2 represents a single bond or —CO—.
    Type: Grant
    Filed: January 9, 2012
    Date of Patent: July 9, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hyungjoo Kim, Akira Kamabuchi, Koji Ichikawa
  • Patent number: 8475997
    Abstract: A resist composition for immersion exposure including: a fluorine-containing polymeric compound (F) containing a structural unit (f1) having a base dissociable group and a structural unit (f2) represented by general formula (f2-1) (wherein R represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; and W is a group represented by any one of general formulas (w-1) to (w-4)); a base component (A) that exhibits changed solubility in an alkali developing solution under the action of acid; and an acid generator component (B) that generates acid upon exposure.
    Type: Grant
    Filed: December 23, 2011
    Date of Patent: July 2, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daiju Shiono, Tomoyuki Hirano, Sanae Furuya, Takahiro Dazai, Hiroaki Shimizu, Tsuyoshi Kurosawa, Hideto Nito, Tsuyoshi Nakamura
  • Patent number: 8470513
    Abstract: A radiation-sensitive resin composition includes a polymer that includes at least one repeating unit (i) selected from a repeating unit shown by a formula (1), (2), and (3); and a repeating unit (ii) shown by a formula (4). R1 represents a hydrogen atom or a methyl group. Each R2 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms. p is an integer from 0 to 3, and q is an integer from 1 to 3, and p+q?5. A chemically-amplified positive-tone resist film that is sensitive to extreme ultraviolet rays (EUV) can be formed using the radiation-sensitive resin composition.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: June 25, 2013
    Assignee: JSR Corporation
    Inventors: Kota Nishino, Ken Maruyama, Daisuke Shimizu, Toshiyuki Kai
  • Patent number: 8470510
    Abstract: A polymer for lithographic purposes has at least a repeating structural unit represented by following General Formula (I). In Formula (I), R1, R3, R4, and R6 each independently represent hydrogen atom, a halogen atom, cyano group, an alkyl group, or a haloalkyl group; R2 and R5 each independently represent hydrogen atom, cyano group, etc.; X1 and X2 each independently represent single bond, or a substituted or unsubstituted bivalent alkylene, alkenylene, or cycloalkylene group, etc.; X3 and X4 each independently represent single bond or —CO—; R7, R8, R9, and R10 each independently represent hydrogen atom, an alkyl group, or a cycloalkyl group. The polymer for lithographic purposes shows good balance between line edge roughness (LER) and etching resistance and allows very fine and uniform patterning.
    Type: Grant
    Filed: June 1, 2009
    Date of Patent: June 25, 2013
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Arimichi Okumura, Keizo Inoue, Kazuki Okamoto
  • Patent number: 8460856
    Abstract: A photosensitive material for use in semiconductor manufacture comprises a copolymer that includes a plurality of photoresist chains and a plurality of hydrophobic chains, each hydrophobic chain attached to the end of one of the photoresist chains. The copolymer in response to externally applied energy will self-assemble to a photoresist layer and a hydrophobic layer.
    Type: Grant
    Filed: September 21, 2011
    Date of Patent: June 11, 2013
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Hsiao-Wei Yeh, Jen-Chieh Shih, Jian-Hong Chen
  • 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: 8455175
    Abstract: Photoresist compositions and methods suitable for depositing a thick photoresist layer in a single coating application are provided. Such photoresist layers are particularly suitable for use in chip scale packaging, for example, in the formation of metal bumps.
    Type: Grant
    Filed: April 26, 2011
    Date of Patent: June 4, 2013
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Mark R. Winkle, Jill E. Steeper, Xiang-Qian Liu, Janet Okada-Coakley, Scott A. Ibbitson
  • Patent number: 8450041
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes (A) a compound capable of generating a specific acid having a norbornyl structure upon irradiation with an actinic ray or radiation, and (B) a resin capable of increasing the dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure on the resin side chain through a linking group, and a pattern forming method uses the composition.
    Type: Grant
    Filed: January 15, 2010
    Date of Patent: May 28, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Shuhei Yamaguchi
  • Patent number: 8450044
    Abstract: A positive resist composition including a resin component (A) which exhibits increased solubility in an alkali developing solution under the action of acid and an acid-generator component (B), the resin component (A) including a polymeric compound (A1) having a structural unit (a1) containing an acid dissociable, dissolution inhibiting group, a structural unit (a5) containing a base dissociable group an a structural unit (a6) represented by general formula (a6-1) (R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; each of R2 and R3 independently represents a hydrogen atom or an alkyl group that may contain an oxygen atom at an arbitrary position, or R2 and R3 are bonded together to form an alkylene group; and W represents a cyclic alkylene group that may include an oxygen atom at an arbitrary position).
    Type: Grant
    Filed: November 12, 2010
    Date of Patent: May 28, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tomoyuki Hirano, Daiju Shiono, Daichi Takaki
  • Patent number: 8440385
    Abstract: A positive resist composition including a base component (A?) which exhibits increased solubility in an alkali developing solution under the action of acid and generates acid upon exposure, the base component (A?) including a resin component (A1) having a structural unit (a0-1) represented by general formula (a0-1), a structural unit (a0-2) which generates acid upon exposure and a structural unit (a1) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group (wherein R1 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, R2 represents a divalent linking group, and R3 represents a cyclic group containing —SO2— within the ring skeleton thereof).
    Type: Grant
    Filed: December 27, 2010
    Date of Patent: May 14, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tomoyuki Hirano, Daiju Shiono, Masatoshi Arai