Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
  • Patent number: 9040220
    Abstract: A resist composition including a base component which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component which generates acid upon exposure, the acid-generator including an acid generator consisting of a compound represented by general formula (b1-1) shown below: In which RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Grant
    Filed: March 2, 2012
    Date of Patent: May 26, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9034556
    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, the acid-generator component (B) including an acid generator (B1) consisting of a compound represented by general formula (b1-1) shown below: wherein RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Grant
    Filed: December 18, 2008
    Date of Patent: May 19, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • 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: 9017918
    Abstract: A polymer is obtained from a hydroxyphenyl methacrylate monomer having an acid labile group substituted thereon. A positive resist composition comprising the polymer as a base resin has a very high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good profile and minimal line edge roughness of a pattern after exposure, a retarded acid diffusion rate, and good etching resistance.
    Type: Grant
    Filed: June 1, 2011
    Date of Patent: April 28, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Seiichiro Tachibana, Koji Hasegawa
  • Patent number: 9017931
    Abstract: A negative pattern is formed by coating a resist composition comprising a polymer comprising recurring units having a tertiary ester type acid labile group having a plurality of methyl or ethyl groups on alicycle and an acid generator onto a substrate, prebaking, exposing to high-energy radiation, baking, and developing in an organic solvent developer so that the unexposed region of resist film is dissolved away and the exposed region of resist film is not dissolved. The resist composition exhibits a high dissolution contrast during organic solvent development and forms a fine hole or trench pattern of dimensional uniformity.
    Type: Grant
    Filed: August 16, 2013
    Date of Patent: April 28, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Jun Hatakeyama, Masayoshi Sagehashi, Teppei Adachi
  • Patent number: 9012123
    Abstract: A positive resist composition and a pattern forming method using the resist composition are provided, the resist composition including: (A) a resin containing a repeating structural unit represented by formula (I) as defined in the specification and being capable of decomposing by an action of an acid to increase the solubility in an alkali developer; (B) an acid generator; and (C) a mixed solvent containing at least one solvent selected from the group consisting of the following Group (a) and at least one solvent selected from the group consisting of the following Groups (b) to (d): Group (a): an alkylene glycol monoalkyl ether, Group (b): an alkylene glycol monoalkyl ether carboxylate, Group (c): a linear ketone, a branched chain ketone, a cyclic ketone, a lactone and an alkylene carbonate, and Group (d): a lactic acid ester, an acetic acid ester and an alkoxypropionic acid ester.
    Type: Grant
    Filed: March 26, 2009
    Date of Patent: April 21, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Kei Yamamoto, Akinori Shibuya
  • Patent number: 9012129
    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) including a compound represented by (b1-1), a compound represented by (b1-1?) and/or a compound represented by (b1-1?) (R1?-R3? represents an aryl group or an alkyl group, provided that at least one of R1?-R3? represents a substituted aryl group being substituted with a group represented by (b1-1-0), and two of R1?-R3? may be mutually bonded to form a ring with the sulfur atom; X represents a C3-C30 hydrocarbon group; Q1 represents a carbonyl group-containing divalent linking group; X10 represents a C1-C30 hydrocarbon group; Q3 represents a single bond or a divalent linking group; Y10 represents —C(?O)— or —SO2—; Y11 represents a C1-C10 alkyl group or a fluorinated alkyl group: Q2 represents a single bond or an alkylene group; and W represents a C2-C10 alkylene group).
    Type: Grant
    Filed: January 6, 2014
    Date of Patent: April 21, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
  • Patent number: 8999621
    Abstract: A pattern forming method includes: (i) forming a film from a chemical amplification resist composition; (ii) exposing the film, so as to form an exposed film; and (iii) developing the exposed film by using an organic solvent-containing developer, wherein the chemical amplification resist composition contains: (A) a resin substantially insoluble in alkali; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (C) a crosslinking agent; and (D) a solvent, a negative chemical amplification resist composition used in the method, and a resist film formed from the negative chemical amplification resist composition.
    Type: Grant
    Filed: October 5, 2010
    Date of Patent: April 7, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Yuichiro Enomoto, Sou Kamimura, Shinji Tarutani, Keita Kato, Kaoru Iwato
  • Patent number: 8993212
    Abstract: A resist composition according to the present invention includes at least a base resin, a photoacid generator and a solvent, wherein the photoacid generator comprises a fluorine-containing sulfonic acid salt of the following general formula (4). In the formula, X independently represents a hydrogen atom or a fluorine atom; n represents an integer of 1 to 6; R1 represents a hydrogen atom, or an alkyl, alkenyl, oxoalkyl, aryl or aralkyl group; any of hydrogen atoms on carbons in R1 may be substituted with a substituent; R2 represents RAO or RBRCN; and A represents a divalent group. This fluorine-containing sulfonic acid salt can serve as a photoacid generator having high solubility in a resist solvent and thus can suitably be used for a resist composition such that the resist composition shows high resolution, wide DOF, small LER and high sensitivity to form a good pattern shape in lithographic processes.
    Type: Grant
    Filed: October 14, 2011
    Date of Patent: March 31, 2015
    Assignee: Central Glass Company, Limited
    Inventors: Ryozo Takihana, Satoru Narizuka
  • Patent number: 8980524
    Abstract: A positive resist composition including a base component (A) which exhibits increased solubility in an alkali developing solution under action of acid, an acid-generator component (B) which generates acid upon exposure and a fluorine-containing polymeric compound (C?) which generates acid upon exposure, the base component (A) having a structural unit (a0-1) represented by general formula (a0-1) and a structural unit (a1) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group, and the fluorine-containing polymeric compound (C?) having a structural unit (c0) which generates acid upon exposure and a structural unit (c1) represented by formula (c1) (wherein R2 represents a divalent linking group, R3 represents a cyclic group containing —SO2— within the ring skeleton, Q0 represents a single bond or a divalent linking group, and R0 represents an organic group which may have a fluorine atom).
    Type: Grant
    Filed: December 27, 2010
    Date of Patent: March 17, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tomoyuki Hirano, Daiju Shiono, Masatoshi Arai
  • Patent number: 8968979
    Abstract: A positive resist composition comprises a polymer comprising repeat units having formula (1) or (2). Herein denotes an aromatic hydrocarbon group, R1 is H, methyl or trifluoromethyl, R2 is H, C1-C12 alkyl or aromatic hydrocarbon group, R3 is C1-C12 alkyl, or R2 and R3 may bond together to form a ring, and a is 1 or 2. When used in the ArF lithography, the resist composition exhibits high resolution. When used in the EB image writing for mask processing, the resist composition exhibits high resolution and sensitivity sufficient to comply with high-accelerating-voltage EB irradiation, and high etch resistance.
    Type: Grant
    Filed: November 20, 2009
    Date of Patent: March 3, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuya Takemura, Keiichi Masunaga, Daisuke Domon, Masayoshi Sagehashi
  • Patent number: 8969483
    Abstract: A photoresist material comprising a polymer with at least two acrylate derivatives incorporated therein, and a photo-acid generator for generating an acid by exposure, wherein at least one of the two acrylate derivatives incorporated therein comprises a norbornyl moiety having a lactone structure, and at least one of the two acrylate derivatives comprises an ester-substituted tetracyclododecyl moiety.
    Type: Grant
    Filed: November 28, 2012
    Date of Patent: March 3, 2015
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
  • Patent number: 8962233
    Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes an arylsulfonium salt that when exposed to actinic rays or radiation, generates an acid, the arylsulfonium salt containing at least one aryl ring on which there are a total of one or more electron donating groups, the acid generated upon exposure to actinic rays or radiation having a volume of 240 ?3 or greater.
    Type: Grant
    Filed: January 28, 2011
    Date of Patent: February 24, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Takeshi Kawabata, Tomotaka Tsuchimura, Takayuki Ito
  • Patent number: 8956803
    Abstract: The present invention provides a sulfonium salt used in a resist composition that can give a pattern having a high resolution, especially an excellent rectangularity of a pattern form and a small roughness, while not readily generating a defect, in the photolithography using a high energy beam as a light source; a resist composition that contains the sulfonium salt; and a patterning process using this resist composition, wherein the sulfonium salt is shown by the following general formula (1a), wherein each of R and R0 independently represents a hydrogen atom, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 30 carbon atoms which may be optionally substituted by a heteroatom or interposed by a heteroatom.
    Type: Grant
    Filed: December 6, 2013
    Date of Patent: February 17, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Tomohiro Kobayashi, Akihiro Seki, Masayoshi Sagehashi, Masahiro Fukushima
  • Patent number: 8945808
    Abstract: Resist compositions that can be used in immersion lithography without the use of an additional topcoat are disclosed. The resist compositions comprise a photoresist polymer, at least one photoacid generator, a solvent; and a self-topcoating resist additive. A method of forming a patterned material layer on a substrate using the resist composition is also disclosed.
    Type: Grant
    Filed: April 28, 2006
    Date of Patent: February 3, 2015
    Assignee: International Business Machines Corporation
    Inventors: Robert Allen David, Phillip Joe Brock, Carl E Larson, Daniel Paul Sanders, Ratnam Sooriyakumaran, Linda Karin Sundberg, Hoa D Truong, Gregory Michael Wallraff
  • Patent number: 8945810
    Abstract: A positive resist composition comprises: (A) a resin that has a repeating unit represented by general formula (a1) and increases its solubility in an alkali developer by action of an acid; (B) a compound which generates an acid upon irradiation with an actinic ray or a radiation; and (C) a resin that has at least one of a fluorine atom and a silicon atom and has a group selected from the group consisting of (x), (y) and (z); and (D) a solvent: (x) an alkali-soluble group; (y) a group capable that decomposes by action of an alkali developer to undergo an increase in a solubility of the resin (C) in an alkali developer; and (z) a group that decomposes by action of an acid, wherein R represents a hydrogen atom or a methyl group, Rxa represents an alkyl group or a cycloalkyl group, and n represents an integer of 1 to 8.
    Type: Grant
    Filed: June 30, 2011
    Date of Patent: February 3, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Fumiyuki Nishiyama, Hiromi Kanda
  • 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: 8932794
    Abstract: A positive photosensitive composition, includes: (A) a resin having a repeating unit represented by formula (1) as defined in the specification and a repeating unit represented by formula (2) as defined in the specification and being capable of increasing a solubility of the resin (A) in an alkali developer by an action of an acid; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; and a solvent, and a pattern forming method uses the positive photosensitive composition.
    Type: Grant
    Filed: September 29, 2009
    Date of Patent: January 13, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Toshiaki Fukuhara, Akinori Shibuya, Takayuki Kato
  • Patent number: 8921027
    Abstract: A radiation-sensitive resin composition includes an acid-labile group-containing resin, and a compound shown by the following general formula (i). R1 represents a hydrogen atom or the like, R2 represents a single bond or the like, R3 represents a linear or branched unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms or the like, and X+ represents an onium cation.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: December 30, 2014
    Assignee: JSR Corporation
    Inventors: Ryuichi Serizawa, Nobuji Matsumura, Hirokazu Sakakibara
  • Patent number: 8921029
    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, R2, RII1, RII2, LII1, YII1, RII3, RII4, RII5, RII6, RII7, n, s and RII8 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: December 30, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
  • Patent number: 8916333
    Abstract: A radiation-sensitive resin composition includes a polymer and a photoacid generator. The polymer includes a first structural unit shown by a formula (a1), a second structural unit shown by a formula (a2), and a third structural unit having a lactone structure. A content of the first structural unit in the polymer being 50 mol % or more based on total structural units included in the polymer. The first structural unit is preferably a structural unit shown by a formula (a1-1).
    Type: Grant
    Filed: September 28, 2012
    Date of Patent: December 23, 2014
    Assignee: JSR Corporation
    Inventors: Hiroshi Tomioka, Noboru Otsuka, Akimasa Soyano
  • Patent number: 8911928
    Abstract: A resist composition including a base component (A) that exhibits changed solubility in a developing solution under action of acid and an acid generator component (B) that generates acid upon exposure, wherein the base component (A) contains a resin component (A1) including a structural unit (a0) represented by general formula (a0-1) shown below and a structural unit (a1)) containing an acid decomposable group that exhibits increased polarity under action of acid, and the amount of the structural unit (a0) is less than 50 mol %, 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; R1 represents a divalent linking group; R2 represents a —SO2— containing cyclic group; and v represents 0 or 1.
    Type: Grant
    Filed: May 22, 2012
    Date of Patent: December 16, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tomoyuki Hirano, Daiju Shiono, Daichi Takaki, Junichi Tsuchiya
  • Patent number: 8900789
    Abstract: An actinic-ray- or radiation-sensitive resin composition comprises (A) a resin that when acted on by an acid, exhibits an increased solubility in an alkali developer, (B) a compound that when exposed to actinic rays or radiation, generates an acid, (C) a resin containing two or more resins (c) each having at least either a fluorine atom or a silicon atom, and (D) a solvent.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: December 2, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hiroshi Saegusa, Shinichi Kanna
  • Patent number: 8900788
    Abstract: A resist composition for immersion exposure, including: a base component (A) which exhibits changed solubility in an alkali developing solution under action of an acid, and contains no structural unit (c1) represented by the general formula (c1-1) shown below; an acid generator component (B) which generates an acid upon exposure; and a fluorine-containing resin component (C) which contains the structural unit (c1) (in the formula (c1-1), R represents a hydrogen atom, a lower alkyl group, a halogen atom, or a halogenated lower alkyl group; Rf represents a fluorinated alkyl group; and Y0 represents an alkylene group).
    Type: Grant
    Filed: October 12, 2007
    Date of Patent: December 2, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Yasuhiro Yoshii
  • Patent number: 8900793
    Abstract: There is disclosed a polymer having a repeating unit shown by the following general formula (1). There can be, in a photolithography using a high energy beam such as an ArF excimer laser beam and an EUV as a light source, (1) a polymer that gives a resist composition having an appropriate adhesion with a substrate and being capable of forming a pattern having excellent resolution, especially an excellent rectangular pattern profile, (2) a chemically amplified resist composition containing the said polymer, and (3) a patterning process using the said chemically amplified resist composition.
    Type: Grant
    Filed: May 21, 2012
    Date of Patent: December 2, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayoshi Sagehashi, Youichi Ohsawa, Koji Hasegawa, Tomohiro Kobayashi
  • Patent number: 8900796
    Abstract: The present invention provides an acid generator generates a sulfonic acid represented by the following general formula (1) in response to high-energy beam or heat: To provide a novel acid generator which is suitably used as an acid generator for a resist composition, which solves the problems of LER and a depth of focus and can be effectively and widely used particularly without degradation of a resolution, a chemically amplified resist composition using the same, and a patterning process.
    Type: Grant
    Filed: February 15, 2013
    Date of Patent: December 2, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Tomohiro Kobayashi, Masayoshi Sagehashi
  • Patent number: 8889333
    Abstract: A salt represented by formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, L2 and L3 respectively represent a single bond or a C1-C6 divalent saturated alkyl group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, ring W1 and ring W2 respectively represent a C3-C36 hydrocarbon ring, R1 and R2 respectively represent a hydrogen atom or C1-C6 alkyl group, R3 represents C1-C6 alkyl group, t represents an integer of 0 to 2 and Z+ represents an organic counter ion.
    Type: Grant
    Filed: April 10, 2012
    Date of Patent: November 18, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Isao Yoshida, Yuko Yamashita
  • Patent number: 8877421
    Abstract: A positive resist composition includes: (A) a resin capable of increasing the solubility in an alkali developing solution by the action of an acid, including: (a1) a repeating unit selected from repeating units represented by following formulae (a1-1) to (a1-3); (a2) a repeating unit represented by a following formula (a2); and (a3) a repeating unit selected from repeating units represented by following formulae (a3-1) to (a3-4); (B) a compound capable of generating an acid upon irradiation with actinic ray or radiation; (C) a resin having at least one of a fluorine atom and a silicon atom, and being insoluble in an alkali developing solution; and (D) a solvent, wherein the formulae above are defined in the specification.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: November 4, 2014
    Assignee: FUJIFILM Corporation
    Inventor: Shinichi Kanna
  • Patent number: 8877424
    Abstract: A polymer is prepared from an adamantane methacrylate monomer whose alcoholic hydroxyl group is protected with an alicyclic-containing tertiary alkyl group. A photoresist composition comprising the polymer displays a high sensitivity and a high dissolution contrast during both alkaline development and organic solvent development.
    Type: Grant
    Filed: February 8, 2013
    Date of Patent: November 4, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayoshi Sagehashi, Jun Hatakeyama, Koji Hasegawa, Kazuhiro Katayama
  • Patent number: 8859180
    Abstract: [Task to Be Achieved] To provide a chemically amplified type positive copolymer for semiconductor lithography, which has eliminated the problems of prior art, has a high development contrast, and has excellent resolution in fine-pattern formation; a composition for semiconductor lithography which contains the copolymer; and a process for producing the copolymer. [Means for Achievement] The copolymer for semiconductor lithography according to the present invention is a copolymer which has at least (A) a repeating unit having a structure which has an alkali-soluble group protected by an acid-labile, dissolution-suppressing group, (B) a repeating group having a lactone structure and (C) a repeating group having an alcoholic hydroxyl group and which is characterized by having an acid value of 0.01 mmol/g or less as determined by dissolving the copolymer in a solvent and subjecting the solution to neutralization titration with a solution of an alkali metal hydroxide using Bromothymol Blue as an indicator.
    Type: Grant
    Filed: October 19, 2007
    Date of Patent: October 14, 2014
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Tomo Oikawa, Takayoshi Okada, Masaaki Kudo, Takanori Yamagishi
  • Patent number: 8859181
    Abstract: A chemically amplified negative resist composition is provided comprising (A) an alkali-soluble base polymer, (B) an acid generator, and (C) a nitrogen-containing compound, the base polymer (A) turning alkali insoluble under the catalysis of acid. A polymer having a fluorinated carboxylic acid onium salt on a side chain is included as the base polymer. Processing the negative resist composition by a lithography process may form a resist pattern with advantages including uniform low diffusion of acid, improved LER, and reduced substrate poisoning.
    Type: Grant
    Filed: February 24, 2011
    Date of Patent: October 14, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Keiichi Masunaga, Satoshi Watanabe, Jun Hatakeyama, Youichi Ohsawa, Daisuke Domon
  • Patent number: 8859187
    Abstract: A novel method of forming a resist pattern in which thickness loss from the resist pattern is reduced, and a negative resist composition that can be used in this method of forming a resist pattern. The method of forming a resist pattern includes: forming a first resist film by applying a first resist composition to a support, forming a first resist pattern by selectively exposing the first resist film through a first mask pattern and then developing the first resist film, forming a second resist film by applying a negative resist composition containing an ether-based organic solvent (S?) having no hydroxyl groups onto the support having the first resist pattern formed thereon, and forming a resist pattern by selectively exposing the second resist film through a second mask pattern and then developing the second resist film.
    Type: Grant
    Filed: October 19, 2007
    Date of Patent: October 14, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Ken Tanaka, Sho Abe, Shigeru Yokoi
  • Patent number: 8846303
    Abstract: There is disclosed a resist top coat composition, used in a patterning process onto a photoresist film, wherein a resist top coat is formed by using the resist top coat composition onto a photoresist film formed on a wafer, and then, after exposure, removal of the resist top coat and development of the photoresist film are performed to effect the patterning on the photoresist film, wherein the resist top coat composition contains a truxene compound having phenol groups shown by the following general formula (1). As a result, there is provided a resist top coat composition not only having an effect from an environment to a resist film reduced and effectively shielding an OOB light, but also reducing film loss of a resist pattern and bridging between patterns and having an effect to enhance sensitivity of the resist; and a patterning process using this.
    Type: Grant
    Filed: September 25, 2012
    Date of Patent: September 30, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Daisuke Kori
  • Patent number: 8846294
    Abstract: The present invention provides a photoresist composition comprising the following components (A), (B) and (X): (A) a resin being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid, (B) an acid generator, (X) at least one compound selected from the group consisting of a compound represented by the formula (I-a): wherein Z1 represent a C1-C20 divalent saturated aliphatic hydrocarbon group in which one or more —CH2— may be replaced by —O— or —CO—, and a compound represented by the formula (I-b): wherein R1 represents a C1-C20 monovalent saturated aliphatic hydrocarbon group in which one or more hydrogen atoms may be substituted with a hydroxyl group and one or more —CH2— may be replaced by —O— or —CO—, and n represents 0 or 1.
    Type: Grant
    Filed: March 29, 2012
    Date of Patent: September 30, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Satoshi Yamaguchi
  • 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: 8846295
    Abstract: The present invention relates to a photoresist composition capable of negative development and a pattern forming method using the photoresist composition. The photoresist composition includes an imaging polymer, a crosslinking agent and a radiation sensitive acid generator. The imaging polymer includes a monomeric unit having an acid-labile moiety-substituted hydroxyl group. The patterning forming method utilizes an organic solvent developer to selectively remove an unexposed region of a photoresist layer of the photoresist composition to form a patterned structure in the photoresist layer. The photoresist composition and the pattern forming method are especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.
    Type: Grant
    Filed: April 27, 2012
    Date of Patent: September 30, 2014
    Assignee: International Business Machines Corporation
    Inventors: Kuang-Jung Chen, Wu-Song Huang, Wai-Kin Li
  • Patent number: 8846293
    Abstract: The actinic ray-sensitive or radiation-sensitive resin composition of the present invention contains (A) a resin capable of increasing the solubility in an alkaline developer by the action of an acid, and (C) at least one selected from the group of compounds represented by the following formula (ZI-3), (ZI-4) or (ZI-5) and capable of generating an acid upon irradiation of actinic rays or radiation, wherein the resin (A) contains at least one repeating unit having a group capable of decomposing by the action of an acid to leave a leaving group having a ring structure, and the leaving group having a ring structure has at least one of a polar group as a substituent and a polar atom as a part of the ring structure, and a compound derived from the leaving group having a ring structure has a logP value of not less than 0 and less than 2.8.
    Type: Grant
    Filed: March 27, 2012
    Date of Patent: September 30, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Yusuke Iizuka, Akinori Shibuya, Naohiro Tango, Shohei Kataoka
  • Patent number: 8841061
    Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1) 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 is methylene or ethylene, R2 is alkyl, aryl, or alkenyl, which may contain oxygen or sulfur, R3 is fluorine or trifluoromethyl, and m is an integer of 1 to 4.
    Type: Grant
    Filed: August 30, 2012
    Date of Patent: September 23, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8835097
    Abstract: There is disclosed a sulfonium salt shown by the following general formula (1). There can be a sulfonium salt capable of introducing an acid-generating unit generating an acid having an appropriate acid strength and not impairing adhesion with a substrate into a base polymer; a polymer using the said sulfonium salt; a chemically amplified resist composition using the said polymer as a base polymer; and a patterning process using the said chemically amplified resist composition.
    Type: Grant
    Filed: May 21, 2012
    Date of Patent: September 16, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Daisuke Domon, Keiichi Masunaga, Satoshi Watanabe
  • Patent number: 8828645
    Abstract: There is disclosed a negative resist composition comprising at least: (A) a base polymer that is alkaline-soluble and is made alkaline-insoluble by action of an acid; (B) an acid generator; and (C) a basic component, wherein the base polymer at least contains a polymer including repeating units represented by the following general formula (1) and general formula (2) and having a weight average molecular weight of 1,000 to 10,000. There can be a negative resist composition hardly causing a bridge in forming a pattern and providing a high resolution and a patterning process using the same.
    Type: Grant
    Filed: October 25, 2013
    Date of Patent: September 9, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Akinobu Tanaka, Keiichi Masunaga, Daisuke Domon, Satoshi Watanabe
  • Patent number: 8822136
    Abstract: A negative pattern is formed by coating a resist composition onto a substrate, the resist composition comprising a polymer comprising recurring units having an acid labile group-substituted hydroxyl group, an acid generator, an onium salt of perfluoroalkyl ether carboxylic acid, and an organic solvent, prebaking, exposing, baking, and developing in an organic solvent such that the unexposed region of film is dissolved away and the exposed region of film is not dissolved. In image formation via positive/negative reversal by organic solvent development, the resist film is characterized by a high dissolution contrast between the unexposed and exposed regions.
    Type: Grant
    Filed: October 26, 2012
    Date of Patent: September 2, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Kazuhiro Katayama, Youichi Ohsawa
  • Patent number: 8808960
    Abstract: A compound represented by the formula (I): wherein R1 represents a hydrogen atom etc., R2 and R3 each independently represent a hydrogen atom etc., R4 represents a C1-C8 divalent hydrocarbon group, R5 represents a single bond etc., and R6 represents an unsubstituted or substituted C6-C20 aromatic hydrocarbon group, a polymer comprising a structural unit derived from the compound represented by the formula (I) and a chemically amplified positive resist composition comprising the polymer, at least one acid generator and at least one solvent.
    Type: Grant
    Filed: March 8, 2010
    Date of Patent: August 19, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Akita, Isao Yoshida, Kazuhiko Hashimoto
  • Patent number: 8808966
    Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal edge roughness. In formula (1), A is —(CR22)m—, B is —(CR52)n—, R2 and R5 are hydrogen or alkyl, m and n are 1 or 2, R3 is alkyl, alkenyl, alkynyl or aryl, R6 is alkyl, alkoxy, alkanoyl, alkoxycarbonyl, hydroxyl, nitro, aryl, halogen, or cyano, and p is 0 to 4.
    Type: Grant
    Filed: July 25, 2012
    Date of Patent: August 19, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8808959
    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) including a compound represented by (b1-1), a compound represented by (b1-1?) and/or a compound represented by (b1-1?) (R1?-R3? represents an aryl group or an alkyl group, provided that at least one of R1?-R3? represents a substituted aryl group being substituted with a group represented by (b1-1-0), and two of R1?-R3? may be mutually bonded to form a ring with the sulfur atom; X represents a C3-C30 hydrocarbon group; Q1 represents a carbonyl group-containing divalent linking group; X10 represents a C1-C30 hydrocarbon group; Q3 represents a single bond or a divalent linking group; Y10 represents —C(?O)— or —SO2—; Y11 represents a C1-C10 alkyl group or a fluorinated alkyl group: Q2 represents a single bond or an alkylene group; and W represents a C2-C10 alkylene group).
    Type: Grant
    Filed: November 10, 2009
    Date of Patent: August 19, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
  • Patent number: 8802347
    Abstract: Coating compositions include a polymer including: wherein R1 is a silicon containing moiety, R2 is an acid stable lactone functionality, and R3 is an acid labile lactone functionality; X1, X2, X3 are independently H or CH3; and m and o are non-zero positive integers and n is zero or a positive integer representing the number of repeat units; a photoacid generator; and a solvent. Also disclosed are methods for forming a pattern in the coating composition containing the same.
    Type: Grant
    Filed: November 6, 2009
    Date of Patent: August 12, 2014
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Phillip J. Brock, Kuang-Jung Chen, Alexander Friz, Wu-Song Huang, Ratnam Sooriyakumaran, Sally A. Swanson, Hoa D. Truong
  • Patent number: 8802348
    Abstract: A radiation-sensitive resin composition includes (A) an acid labile group-containing resin which becomes alkali-soluble by an action of an acid, (B) a radiation-sensitive acid generator, and (C) a solvent. The resin (A) includes repeating units shown by formulas (1) and (2), wherein R1 and R2 represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, R3 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, X represents a hydrogen atom, a hydroxyl group, or an acyl group, m represents an integer from 1 to 18, and n represents an integer from 4 to 8.
    Type: Grant
    Filed: February 7, 2010
    Date of Patent: August 12, 2014
    Assignee: JSR Corporation
    Inventors: Noboru Otsuka, Takanori Kawakami, Yukio Nishimura, Makoto Sugiura
  • Patent number: 8802783
    Abstract: A photoresist material comprising a polymer with at least two acrylate derivatives incorporated therein, and a photo-acid generator for generating an acid by exposure, wherein at least one of the two acrylate derivatives incorporated therein comprises a norbornyl moiety having a lactone structure, and at least one of the two acrylate derivatives comprises an ester-substituted tetracyclododecyl moiety.
    Type: Grant
    Filed: November 28, 2012
    Date of Patent: August 12, 2014
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
  • Patent number: 8802349
    Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition including: (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, the resin containing (a) a repeating unit represented by the following formula (AN-01), (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a resin that contains at least either a fluorine atom or a silicon atom and contains a repeating unit having a group capable of decomposing by the action of an alkali developer to increase the solubility in an alkali developer: wherein the variables in formula (AN-01) are defined in the description.
    Type: Grant
    Filed: March 31, 2010
    Date of Patent: August 12, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Masahiro Yoshidome, Shuji Hirano, Hiroshi Saegusa, Kaoru Iwato, Yusuke Iizuka
  • Patent number: 8795946
    Abstract: Polymerizable ester compounds having formula (1) are novel wherein R1 is H, F, methyl or trifluoromethyl, R2 is an acid labile group, Aa is a divalent hydrocarbon group which may be separated by —O— or —C(?O)—, and k1 is 0 or 1. They are useful as monomers to produce polymers which are transparent to radiation ?500 nm. Radiation-sensitive resist compositions comprising the polymers as base resin exhibit excellent developed properties.
    Type: Grant
    Filed: July 13, 2012
    Date of Patent: August 5, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Masayoshi Sagehashi, Yuuki Suka, Masashi Ilo
  • Patent number: 8795944
    Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition including: (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a resin which contains (c) a repeating unit having at least one polarity conversion group and has at least either a fluorine atom or a silicon atom.
    Type: Grant
    Filed: December 11, 2009
    Date of Patent: August 5, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hiroshi Saegusa, Kaoru Iwato, Shuji Hirano, Yusuke Iizuka