Patents Examined by John Chu
  • Patent number: 8227169
    Abstract: There are provided a compound preferable as an acid generator for a resist composition, an acid generator including the compound, a resist composition containing the acid generator, and a method of forming a resist pattern using the resist composition, and the compound is represented by general formula (b1-12) shown below: R2—CH2—O—Y1—SO3?A+??(b1-12) wherein R2 represents a monovalent aromatic organic group; Y1 represents an alkylene group of 1 to 4 carbon atoms which may be fluorinated; and A+ represents a cation.
    Type: Grant
    Filed: April 4, 2008
    Date of Patent: July 24, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehito Seo, Hideo Hada, Kotaro Endo, Daisuke Kawana, Yasuhiro Yoshii, Tsuyoshi Kurosawa
  • Patent number: 8221961
    Abstract: The present invention relates to a method of manufacturing semiconductor devices. According to the method, an etch target layer, a chemically amplified photoresist layer, and an Anti-Reflective Coating (ARC) layer are first sequentially formed over a semiconductor substrate. An exposure process is performed in order to form exposure portions in the photoresist layer. A thermal process is performed so that a decrosslinking reaction is generated in the ARC layer on the exposure portions. A development process is performed in order to form photoresist layer patterns and ARC layer patterns by removing the ARC layer at portions in which the decrosslinking reaction has occurred and the exposure portions. A silylation process is performed in order to form silylation patterns on sidewalls of each of the photoresist layer patterns. The ARC layer patterns and the photoresist layer patterns are removed. The etch target layer is patterned using the silylation patterns as an etch mask.
    Type: Grant
    Filed: December 30, 2008
    Date of Patent: July 17, 2012
    Assignee: Hynix Semiconductor Inc.
    Inventor: Guee Hwang Sim
  • Patent number: 8216763
    Abstract: A photosensitive resin composition which has a quenching function and satisfactory long-term stability and which, in particular, can be prevented from suffering sensitivity abnormality caused by change with time during storage (change from given sensitivity); and a method of forming a pattern from the composition. The resist composition contains a base resin comprising, as the main component, a silicon-containing polymer which is a siloxane or silsesquioxane polymer or the like, the composition containing, as a quencher, a specific sulfonium compound in place of a nitrogenous compound.
    Type: Grant
    Filed: October 10, 2006
    Date of Patent: July 10, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazufumi Sato, Yasushi Fujii, Hisanobu Harada, Koji Yonemura, Isamu Takagi, Daisuke Kawana, Tomotaka Yamada, Toshikazu Takayama
  • 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: 8211618
    Abstract: A positive resist composition comprising as a base resin a polymer having carboxyl groups whose hydrogen is substituted by an acid labile group of acenaphthene structure exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal LER after exposure, a significant effect of suppressing acid diffusion rate, and improved etching resistance.
    Type: Grant
    Filed: March 8, 2010
    Date of Patent: July 3, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Seiichiro Tachibana
  • Patent number: 8211614
    Abstract: Disclosed is a resist composition which has desirable physical properties such as sensitivity, resolution, residual film ratio and coating property, and forms a pattern having the desirable profile and depth of focus due to excellent light transmissivity during a semiconductor process and a flat panel display process using a short wavelength of 248 nm (KrF) or less, even though the resist composition is applied to a non-chemically amplified resist. The photoresist composition comprises a novolac-based resin A, a photosensitizer B, and a low molecular substance C having low absorbance. The low molecular substance having low absorbance has absorbance that is lower than absorbance of the novolac-based resin at one or more wavelengths of 248 nm, 193 nm, and 157 nm, and the photoresist composition is used at the wavelength of 248 nm or less.
    Type: Grant
    Filed: August 2, 2007
    Date of Patent: July 3, 2012
    Assignee: Dongwoo Fine-Chem. Co., Ltd.
    Inventors: Shi-Jin Sung, Sang-Haeng Lee, Sang-Tae Kim
  • Patent number: 8206888
    Abstract: It is intended to provide a radiation-sensitive resin composition, which comprises a radiation-sensitive acid generator excellent in resolution performance, heat stability, and storage stability, suppresses fluctuations in line width and deterioration in pattern profile attributed to standing waves, and produces a resist pattern improved in nano edge roughness and LEF. The radiation-sensitive resin composition is characterized by (A) a radiation-sensitive acid generator comprising: a sulfonium salt compound typified by 2,4,6-trimethylphenyldiphenylsulfonium 2,4-difluorobenzenesulfonate, 2,4,6-trimethylphenyldiphenylsulfonium 4-trifluoromethylbenzenesulfonate, or the like; and a sulfonimide compound. It is preferred that the composition should further comprise (B) a resin typified by a 4-hydroxystyrene/4-t-butoxystyrene copolymer, a 4-hydroxystyrene/t-butyl (meth)acrylate, or the like.
    Type: Grant
    Filed: November 21, 2006
    Date of Patent: June 26, 2012
    Assignee: JSR Corporation
    Inventors: Yuuji Yada, Tomoki Nagai
  • Patent number: 8206891
    Abstract: A positive resist composition including: a base component (A) which includes a polymeric compound (A1) containing a structural unit (a0) represented by the general formula (a0-1) and a structural unit (a1) derived from an acrylate ester having an acid dissociable, dissolution inhibiting group; and an acid generator component (B) which includes an acid generator (B1) containing an anion moiety represented by the general formula (I): (in the formula (a0-1), R1 represents a hydrogen atom, a lower alkyl group of 1 to 5 carbon atoms or a halogenated lower alkyl group of 1 to 5 carbon atoms; R2 represents a bivalent linking group; and R3 represents a cyclic group containing —SO2— within the ring skeleton. In the formula (I), X represents a cyclic group of 3 to 30 carbon atoms, Q1 represents a bivalent linking group containing an oxygen atom; Y1 represents an alkylene group of 1 to 4 carbon atoms or a fluorinated alkylene group of 1 to 4 carbon atoms).
    Type: Grant
    Filed: October 5, 2009
    Date of Patent: June 26, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Akiya Kawaue, Takahiro Dazai, Tomoyuki Hirano, Fumitake Kaneko, Kotaro Endo
  • Patent number: 8198002
    Abstract: Disclosed is a positive photosensitive resin composition that includes (A) a first polybenzoxazole precursor that includes: a repeating unit of Chemical Formula 1 and a thermally polymerizable functional group at at least one terminal end; (B) a second polybenzoxazole precursor that includes a repeating unit of Chemical Formula 3; (C) a photosensitive diazoquinone compound; (D) a silane compound; and (E) a solvent.
    Type: Grant
    Filed: October 20, 2009
    Date of Patent: June 12, 2012
    Assignee: Cheil Industries Inc.
    Inventors: Doo-Young Jung, Ji-Young Jeong, Hyun-Yong Cho, Yong-Sik Yoo, Min-Kook Chung, Jong-Hwa Lee, Kil-Sung Lee, Myoung-Hwan Cha
  • Patent number: 8198007
    Abstract: This disclosure provides a negative-working resist composition comprising a calix resorcinarene derivative (A) of specific structure, an acid generator (B) which directly or indirectly generates an acid when exposed to an active energy ray having a wavelength of 248 nm or less, and a cross-linking agent (C).
    Type: Grant
    Filed: November 5, 2008
    Date of Patent: June 12, 2012
    Assignee: Dai Nippon Printing Co., Ltd.
    Inventors: Kenichi Okuyama, Satoru Kanke
  • Patent number: 8182977
    Abstract: A polymer includes a repeating unit (a-1) shown by a following formula (a-1), a repeating unit (a-2) shown by a following formula (a-2), and a GPC weight average molecular weight of about 1000 to about 100,000, wherein R0 represents an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is substituted by a hydroxyl group, and R1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group, wherein R1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group, R2 represents an alkyl group having 1 to 4 carbon atoms, and R3 represents an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted monovalent cyclic hydrocarbon group having 4 to 20 carbon atoms, or a divalent cyclic hydrocarbon group having 4 to 20 carbon atoms formed by R3 and R3 bonding to each other together with a carbon atom.
    Type: Grant
    Filed: March 23, 2010
    Date of Patent: May 22, 2012
    Assignee: JSR Corporation
    Inventors: Norihiko Ikeda, Hiromitsu Nakashima, Saki Harada
  • Patent number: 8173352
    Abstract: A resist composition comprising: (A) a resin comprising a structural unit having an acid-labile group in its side chain and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, Z1 represents a single bond or —(CH2)k—CO—O—, k represents an integer of 1 to 4, and ring X represents an unsubstituted or substituted C3-C30 cyclic hydrocarbon group having —COO—, (B) a resin comprising a structural unit having an acid-labile group in its side chain and a structural unit represented by the formula (III): wherein R6 represents a hydrogen atom or a methyl group, R7 is independently in each occurrence a linear or branched chain C1-C6 alkyl group and n represents an integer of 0 to 4, and (C) an acid generator.
    Type: Grant
    Filed: November 30, 2009
    Date of Patent: May 8, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Nobuo Ando
  • Patent number: 8173353
    Abstract: The present invention provides a sulfonium compound represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, R1 represents a C5-C42 organic group having a ?-ketoester structure and A+ represents an organic counter ion, and a chemically amplified photoresist composition comprising the above-mentioned sulfonium compound and a resin comprising a structural unit having an acid-labile group and being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid.
    Type: Grant
    Filed: March 23, 2010
    Date of Patent: May 8, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Junji Shigematsu, Hanwoo Park
  • Patent number: 8173357
    Abstract: The method of forming an etching mask includes: forming a mask layer on an object layer that is to be etched, to form an etching mask used in etching the object layer; forming a first mask layer on the mask layer, the first mask layer having a first pattern that is to be transferred onto the mask layer; forming a second mask layer on the first mask layer, the second mask layer having a second pattern that is to be transferred onto the mask layer; obtaining a third mask layer having the first pattern and the second pattern, by transferring the second pattern of the second mask layer onto the first mask layer; and forming the etching mask used in the etching of the object layer, by etching the mask layer using the third mask layer.
    Type: Grant
    Filed: March 19, 2009
    Date of Patent: May 8, 2012
    Assignee: Tokyo Electron Limited
    Inventor: Eiichi Nishimura
  • Patent number: 8173354
    Abstract: A sulfonium salt having a triphenylsulfonium cation and a sulfite anion within the molecule is best suited as a photoacid generator in chemically amplified resist compositions. Upon exposure to high-energy radiation, the sulfonium salt generates a sulfonic acid, which facilitates efficient scission of acid labile groups in chemically amplified positive resist compositions. Because of substantial non-volatility under high vacuum conditions in the EB or EUV lithography, the risk of the exposure tool being contaminated is minimized.
    Type: Grant
    Filed: July 7, 2010
    Date of Patent: May 8, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi
  • Patent number: 8168366
    Abstract: The present invention relates to a radiation sensitive photoresist composition. The composition comprises a polymer comprising at least two monomers. The first monomer has an acid cleavable tertiary ester group. The second monomer is an acidic monomer. The acid cleavable ester group of the polymer has a surprisingly low activation energy which results in improved resist images in lithographic processes.
    Type: Grant
    Filed: October 16, 2008
    Date of Patent: May 1, 2012
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D Truong
  • Patent number: 8163461
    Abstract: The invention provides various photoacid generator compounds and ionic components thereof. Photoresist compositions that include the ions and non-ionic photoacid generator compounds are also provided. The invention further provides methods of making and using the photoacid generator compounds and photoresist compositions disclosed herein. The compounds and compositions are useful as photoactive components in chemically amplified resist compositions for use in, for example, various microfabrication applications.
    Type: Grant
    Filed: April 9, 2009
    Date of Patent: April 24, 2012
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Yi Yi
  • Patent number: 8158327
    Abstract: A compound represented by the following formula (1) is provided: wherein R1 represents a hydrogen atom, a trifluoromethyl group, an alkyl group, or an alkoxy group; and A represents a group represented by the following formula (2) or formula (3): wherein R2, R3, R4, R5 and R6 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted allyl group, a substituted or unsubstituted perfluoroalkyl group, a substituted or unsubstituted benzyl group, or a substituted or unsubstituted aryl group; and two or more of R2, R3 and R4 may be linked to each other to form a saturated or unsaturated carbon ring or a saturated or unsaturated heterocyclic ring. The chemically amplified resist composition comprising a polymer compound which is produced from the compound of formula 1 according to the present invention provides a chemically amplified resist sensitive to far-ultraviolet radiation, which is represented by KrF excimer laser or ArF excimer laser.
    Type: Grant
    Filed: January 15, 2009
    Date of Patent: April 17, 2012
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Hyun-Sang Joo, Joo-Hyeon Park, Jung-Hoon Oh, Dae-Hyeon Shin
  • Patent number: 8158324
    Abstract: A positive-type photosensitive resin composition, including: (a) a novolac resin; (b) a polymer including, as a main component, a structure represented by formula (1) and/or formula (2): ?(wherein R1 and R2 may be the same or different and each represent an organic group having at least two carbon atoms and a valence of 2 to 8, R3 and R4 may be the same or different and each represent hydrogen or a monovalent organic group of 1 to 20 carbon atoms, —NH—R5 in formula (1) and —CO—R6 in formula (2) each represent a polymer end group, R5 and R6 each represent a monovalent organic group having 2 to 30 carbon atoms which includes an unsaturated hydrocarbon group, n is in the range of 10 to 100,000, l and m each represent an integer of 0 to 2, and p and q each represent an integer of 0 to 4, provided that p+q>0; (c) a quinone diazide compound; (d) an alkoxymethyl group-containing compound; and (e) a solvent.
    Type: Grant
    Filed: February 5, 2008
    Date of Patent: April 17, 2012
    Assignee: TORAY Industries, Inc.
    Inventors: Yoji Fujita, Shinji Arimoto, Rinsei Ike
  • Patent number: 8158330
    Abstract: A protective coating composition comprising a copolymer of an alkali-soluble (?-trifluoromethyl) acrylate and a norbornene derivative as a base polymer, optionally in admixture with a second polymer containing sulfonic acid and/or sulfonic acid amine salt in repeat units is applied onto a resist film. The protective coating is effective in minimizing development defects and forming a resist pattern of improved profile.
    Type: Grant
    Filed: May 11, 2009
    Date of Patent: April 17, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Koji Hasegawa, Satoshi Shinachi