Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
  • Patent number: 7601480
    Abstract: The present application relates to a compound of formula where X is selected from the group CF3SO3, C4F9SO3, N(SO2C2F5)2, N(SO2CF3SO2C4F9), N(SO2C3F7)2, N(SO2C4F9)2, CF3CHFO(CF2)2SO3, and CH3CH2CH2O(CF2)4SO3. A photoresist composition comprising a polymer containing an acid labile group, the above compounds, and one or more additional photoacid generators is also provided for.
    Type: Grant
    Filed: December 20, 2006
    Date of Patent: October 13, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: M. Dalil Rahman, Takanori Kudo
  • Patent number: 7598015
    Abstract: A (meth)acrylic copolymer is endowed with a good profile of rigidity and hydrophilicity by introducing not only polycyclic structure units, but also recurring units having a high polarity. A chemically amplified positive resist composition comprising the polymer has a high sensitivity, resolution and etch resistance and improved substrate adhesion and developer affinity.
    Type: Grant
    Filed: June 20, 2005
    Date of Patent: October 6, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Seiichiro Tachibana, Takeru Watanabe, Tsunehiro Nishi
  • Patent number: 7598017
    Abstract: A negative resist composition including: a fluorine-containing resin component (F) containing a structural unit (f1) represented by a general formula (f1-0) shown below, and a structural unit (f2) having an alkali-soluble group, an alkali-soluble resin component (A) excluding the fluorine-containing resin component (F), an acid generator component (B) that generates acid upon exposure, and a cross-linking component (C). [wherein, R7 represents a fluorinated alkyl group, and a represents either 0 or 1.
    Type: Grant
    Filed: October 24, 2008
    Date of Patent: October 6, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Jun Iwashita, Kazuhito Sasaki, Sho Abe
  • Patent number: 7598016
    Abstract: To a resist composition comprising a polymer which changes its alkali solubility under the action of an acid as a base resin, is added a copolymer comprising recurring units containing a carboxylic acid ammonium salt and recurring units containing at least one fluorine atom as an additive. The composition is suited for immersion lithography.
    Type: Grant
    Filed: March 21, 2008
    Date of Patent: October 6, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Kobayashi, Jun Hatakeyama, Yuji Harada
  • Patent number: 7592125
    Abstract: New positive photoresist compositions are provided that contain a photoactive component and blend of at least two distinct resins: i) a first resin that comprises carbocyclic aryl units with hetero substitution (particularly hydroxy or thio) and ii) a second cross-linked resin. Preferred photoresists of the invention can be imaged at short wavelengths, such as sub-200 nm, particularly 193 nm.
    Type: Grant
    Filed: January 19, 2006
    Date of Patent: September 22, 2009
    Assignee: Rohm and Haas Electric Materials LLC
    Inventors: Yasuhiro Suzuki, Cheng-Bai Xu
  • Patent number: 7592126
    Abstract: A positive resist composition comprising: (A) a resin insoluble or sparingly soluble in an alkali but capable of decomposing under an action of an acid to increase a solubility in an alkali developer, the resin having a ?-(meth)acroyloxy-?-butyrolactone repeating unit represented by the following formula (1) containing a lactone ring which may have a substituent; and (B) a compound capable of generating an organic acid represented by the formula (2), (3), (3?), (4) or (5) as defined herein upon irradiation of actinic rays or radiation.
    Type: Grant
    Filed: March 17, 2006
    Date of Patent: September 22, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Fumiyuki Nishiyama
  • Patent number: 7592118
    Abstract: A positive resist composition, includes: (B) a resin containing a repeating unit represented by formula (Ia) or (Ib) as defined in the specification, which decomposes under an action of an acid to increase a solubility of the resin (B) in an aqueous alkali solution; and (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation, and a pattern forming method uses the composition.
    Type: Grant
    Filed: March 24, 2008
    Date of Patent: September 22, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Kazuyoshi Mizutani, Shuji Hirano, Shinichi Sugiyama
  • Patent number: 7582409
    Abstract: A negative resist composition that includes an alkali-soluble resin component, an acid generator component that generates acid upon exposure, and a cross-linker component, wherein the alkali-soluble resin component is a copolymer that includes a structural unit containing an aliphatic cyclic group having a fluorinated hydroxyalkyl group, and a structural unit derived from an acrylate ester that contains a hydroxyl group-containing aliphatic cyclic group, and the cross-linker component includes an alkylene urea-based cross-linker.
    Type: Grant
    Filed: June 16, 2006
    Date of Patent: September 1, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Jun Iwashita, Ayako Kusaka
  • Patent number: 7579132
    Abstract: The present invention provides a salt represented by the formula (I): wherein X represents an n-valent connecting group, Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, n represents 2 or 3, and A+ represents an organic counter ion. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).
    Type: Grant
    Filed: June 4, 2007
    Date of Patent: August 25, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukako Harada, Isao Yoshida, Satoshi Yamaguchi
  • Patent number: 7575846
    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: January 29, 2004
    Date of Patent: August 18, 2009
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Hikaru Momose, Atsushi Ootake, Akifumi Ueda, Tadayuki Fujiwara, Masaru Takeshita, Ryotaro Hayashi, Takeshi Iwai
  • Patent number: 7575850
    Abstract: The present invention provides a chemically amplified resist composition comprising: a resin which comprises a structural unit having an acid-labile group and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X represents a C3-C30 cyclic hydrocarbon group in which one —CH2— is substituted with —COO—, and at least one hydrogen atom in the C3-C30 cyclic hydrocarbon group may be substituted, and p represents an integer of 1 to 4, and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, and at least two salts selected from a salt represented by the formula (II): wherein Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, A+ represents an organic counter ion and R21 represents a C1-C30 hydrocarbon group which may be substituted and at least one —CH2— in the C1-C30 hydrocarbon group may be substituted with —CO
    Type: Grant
    Filed: January 28, 2008
    Date of Patent: August 18, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiyuki Takata, Satoshi Yamamoto, Satoshi Yamaguchi
  • Patent number: 7572570
    Abstract: The present invention provides a chemically amplified resist composition comprising: (A) a resin which comprises (a) a structural unit having an acid-labile group, (b) a structural unit having at least one hydroxyl group, (c) a structural unit having at least one lactone structure, and (d) a structural unit represented by the formula (Ia) or (Ib): wherein R1 represents a hydrogen atom or a methyl group, R3 represents a methyl group, n represents an integer of 0 to 14, and Z represents a single bond or —[CH2]k—COO—, and (B) at least one acid generator.
    Type: Grant
    Filed: March 20, 2008
    Date of Patent: August 11, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yusuke Fuji, Yoshiyuki Takata
  • Patent number: 7569326
    Abstract: A sulfonium salt having a polymerizable anion generates a strong sulfonic acid upon exposure to high-energy radiation so that it facilitates effective scission of acid labile groups in chemically amplified resist compositions. It is useful as a monomer from which a base resin for use in radiation-sensitive resist compositions is derived.
    Type: Grant
    Filed: October 25, 2007
    Date of Patent: August 4, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama, Takeru Watanabe
  • Patent number: 7569325
    Abstract: A photoresist monomer having a sulfonyl group, a polymer thereof and a photoresist composition containing the same are disclosed. The photoresist monomer is represented by following Formula. wherein, R* is a hydrogen atom or a methyl group, R1 and R2 are independently a C1˜C20 alkyl group, a C4˜C20 cycloalkyl group, a C6˜C20 aryl group or a C7˜C20 arylalkyl group, one of R1 and R2 may not exist, and R1 and R2 can be connected to form a ring.
    Type: Grant
    Filed: October 24, 2007
    Date of Patent: August 4, 2009
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jung-Youl Lee, Geun-Jong Yu, Sang-Jung Kim, Jae-Woo Lee, Deog-Bae Kim, Jae-Hyun Kim
  • Patent number: 7569323
    Abstract: A resist protective coating material is provided comprising an ?-trifluoromethylacrylic acid/norbornene copolymer having cyclic perfluoroalkyl groups as pendant. In a pattern-forming process, the material forms on a resist film a protective coating which is water-insoluble, dissolvable in alkaline developer and immiscible with the resist film, allowing for effective implementation of immersion lithography.
    Type: Grant
    Filed: July 26, 2006
    Date of Patent: August 4, 2009
    Assignees: Shin-Etsu Chemical Co., Ltd., Panasonic Corporation, Central Glass Co., Ltd.
    Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai, Masayuki Endo, Masaru Sasago, Haruhiko Komoriya, Michitaka Ootani, Satoru Miyazawa, Kazuhiko Maeda
  • Patent number: 7569328
    Abstract: The present invention provides a resin composition that includes (A) a polymer compound that has, on a side chain of a main chain polymer, through a linkage group containing a hydrogen-bonding group and a ring structure, a terminal ethylenic unsaturated bond, and is soluble or swelling in water or an alkali aqueous solution, and (B) a compound that generates radicals when exposed to light or heat. The invention further provides a thermo/photosensitive composition that includes (A?) a polymer compound that has a non-acidic hydrogen-bonding group on a side chain and is soluble or swelling in water or an alkali aqueous solution, and (B?) a compound that generates radicals when exposed to light or heat.
    Type: Grant
    Filed: August 12, 2003
    Date of Patent: August 4, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Kazuhiro Fujimaki
  • Patent number: 7566522
    Abstract: The present invention provides a chemically amplified resist composition comprising a resin which comprises a structural unit having an acid-labile group and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X represents a C3-C30 cyclic hydrocarbon group in which one —CH2— is substituted with —COO—, and at least one hydrogen atom in the C3-C30 cyclic hydrocarbon group may be substituted, and p represents an integer of 1 to 4, and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, and a salt represented by the formula (II): wherein Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, A+ represents an organic counter ion, and R21 represents a C1-C30 hydrocarbon group which may be substituted and at least one —CH2— in the C1-C30 hydrocarbon group may be substituted with —CO— or —O—.
    Type: Grant
    Filed: December 11, 2007
    Date of Patent: July 28, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiyuki Takata, Takayuki Miyagawa, Kunishige Edamatsu
  • Patent number: 7550249
    Abstract: Base soluble polymer comprising at least one sulfonyl group where at least one carbon atom at ?-position and/or ?-position and/or ?-position with respect to the sulfonyl group has a hydroxyl group, where the hydroxyl group is protected or unprotected are described.
    Type: Grant
    Filed: March 10, 2006
    Date of Patent: June 23, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: David Abdallah, Francis Houlihan
  • Patent number: 7544460
    Abstract: A resist composition is disclosed that enables formation of a favorable resist pattern using a shrink process in which, following formation of the resist pattern, a treatment such as heating is used to narrow the resist pattern, and also disclosed are a laminate and a method for forming a resist pattern that use such a resist composition. This resist composition includes a resin component (A) that displays changed alkali solubility under the action of acid, and an acid generator component (B) that generates acid on exposure. The component (A) contains structural units derived from a (meth)acrylate ester, and exhibits a glass transition temperature that falls within a range from 120 to 170° C.
    Type: Grant
    Filed: July 7, 2004
    Date of Patent: June 9, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Kazuhito Sasaki, Satoshi Fujimura, Takeshi Iwai
  • Patent number: 7541138
    Abstract: A resist composition which is stable relative to solvents used in immersion lithography processes and displays excellent sensitivity and resist pattern profile, and a method of forming a resist pattern that uses such a resist composition are provided. The resist composition is in accordance with predetermined parameters, or is a positive resist composition comprising a resin component (A) which contains an acid dissociable, dissolution inhibiting group and displays increased alkali solubility under the action of acid, an acid generator component (B), and an organic solvent (C), wherein the component (A) contains a structural unit (a1) derived from a (meth)acrylate ester containing an acid dissociable, dissolution inhibiting group, but contains no structural units (a0), including structural units (a0-1) containing an anhydride of a dicarboxylic acid and structural units (a0-2) containing a phenolic hydroxyl group.
    Type: Grant
    Filed: January 10, 2007
    Date of Patent: June 2, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Taku Hirayama, Hideo Hada, Satoshi Fujimura, Takeshi Iwai, Mitsuru Sato, Ryoichi Takasu, Toshikazu Tachikawa, Jun Iwashita, Keita Ishiduka, Tomotaka Yamada, Toshikazu Takayama, Masaaki Yoshida
  • Patent number: 7541131
    Abstract: The invention provides a resist composition for use in the production process of a semiconductor such as IC, in the production of a circuit substrate of liquid crystal, thermal head and the like or in other photofabrication processes, a compound for use in the resist composition and a pattern forming method using the resist composition, which are a resist composition comprising (A) a sulfonium salt represented by the following formula (I); and a pattern forming method using the resist composition: wherein R1 represents an alkyl group or an aryl group, R2 to R9 each independently represents a hydrogen atom or a substituent and may combine with each other to form a ring, Z represents an electron-withdrawing divalent linking group, Xn? represents an n-valent anion, n represents an integer of 1 to 3, and m represents the number of anions necessary for neutralizing the electric charge.
    Type: Grant
    Filed: February 17, 2006
    Date of Patent: June 2, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Yasutomo Kawanishi
  • Patent number: 7541133
    Abstract: A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid, and (B) an acid generator. The resin (A) is a polymer comprising tertiary alkyl protective group units having a hydrophobic tetracyclo[4.4.0.12,5.17,10]-dodecane structure, hydroxyadamantane units, monocyclic lactone units, and carboxylic acid units. The acid generator (B) is a specific sulfonium salt compound.
    Type: Grant
    Filed: November 20, 2007
    Date of Patent: June 2, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Seiichiro Tachibana, Katsuhiro Kobayashi
  • Patent number: 7537880
    Abstract: To a resist composition, an alkali-soluble polymer having fluorinated ester-containing lactone units incorporated therein is included as an additive. The resist composition forms a resist film having a reduced contact angle after development. The resist film prevents water penetration during immersion lithography.
    Type: Grant
    Filed: October 3, 2007
    Date of Patent: May 26, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Takao Yoshihara, Wataru Kusaki, Tomohiro Kobayashi, Koji Hasegawa
  • Patent number: 7537879
    Abstract: The present invention relates to a novel chemically amplified photoresist, which is sensitive to wavelengths between 300 nm and 100 nm, and comprises a) a novel polymer comprising a sulfone group pendant from a polymer backbone that is insoluble in an aqueous alkaline solution and comprises at least one acidic moiety protected with acid labile group, and b) a compound capable of producing an acid upon irradiation. The invention also relates to a process of imaging the novel positive photoresist composition.
    Type: Grant
    Filed: November 22, 2004
    Date of Patent: May 26, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Francis M. Houlihan, Ralph R. Dammel, Andrew R. Romano, Munirathna Padmanaban, M. Dalil Rahman
  • Patent number: 7534548
    Abstract: A polymer for immersion lithography comprising a repeating unit represented by Formula 1 and a photoresist composition containing the same. A photoresist film formed by the photoresist composition of the invention is highly resistant to dissolution, a photoacid generator in an aqueous solution for immersion lithography, thereby preventing contamination of an exposure lens and deformation of the photoresist pattern by exposure.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: May 19, 2009
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Cheol Kyu Bok, Chang Moon Lim, Seung Chan Moon
  • Patent number: 7534551
    Abstract: An objective is to provide a planographic printing plate material exhibiting excellent developability, printing durability, together with excellent oxygen-shielding layer adhesion and moisture dependence after exposure. Disclosed is a planographic printing plate material possessing a support provided thereon, a photosensitive layer, wherein the photosensitive layer comprises (A) at least two binder polymers comprising different glass transition points (Tg) from each other, (B) a polymerizable ethylenic double bond-containing compound, and (C) a photopolymerization initiator.
    Type: Grant
    Filed: January 30, 2007
    Date of Patent: May 19, 2009
    Assignee: Konica Minolta Medical & Graphic, Inc.
    Inventor: Kunio Tani
  • Patent number: 7534550
    Abstract: A positive resist composition includes a resin component (A) and an acid generator component (B), wherein the component (A) is a copolymer that includes a structural unit (a1) derived from an (?-lower alkyl)acrylate ester that contains a monocyclic or polycyclic group-containing acid dissociable, dissolution inhibiting group, a structural unit (a2) derived from an (?-lower alkyl)acrylate ester that contains a lactone ring, a structural unit (a3) derived from an (?-lower alkyl)acrylate ester that contains a polar group-containing polycyclic group, and a structural unit (a4).
    Type: Grant
    Filed: April 7, 2005
    Date of Patent: May 19, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Takeshi Iwai
  • Patent number: 7534549
    Abstract: A photoresist polymer comprising a fluorine component, a photoresist composition containing the photoresist polymer and an organic solvent to reduce surface tension, and a method for manufacturing a semiconductor device using the same by forming a photoresist film uniformly on the whole surface of an underlying layer pattern to allow a subsequent ion-implanting process to be performed stably.
    Type: Grant
    Filed: December 20, 2005
    Date of Patent: May 19, 2009
    Assignee: Hynix Semiconductor Inc.
    Inventor: Jae Chang Jung
  • Patent number: 7531286
    Abstract: 1. A radiation-sensitive resin composition comprising: (A) a resin insoluble or scarcely soluble in alkali, but becomes alkali soluble by the action of an acid and (B) a photoacid generator. The resin comprises (a) at least one recurring unit of the following formula (1-1) or (1-2), and (b) at least one recurring unit for the following formula (2-1), (2-2), or (2-3).
    Type: Grant
    Filed: March 13, 2003
    Date of Patent: May 12, 2009
    Assignee: JSR Corporation
    Inventors: Yukio Nishimura, Hiroyuki Ishii, Masafumi Yamamoto, Isao Nishimura
  • Patent number: 7527912
    Abstract: Photoacid generators generate sulfonic acids of formula (1a) upon exposure to high-energy radiation. RC(?O)R1—COOCH(CF3)CF2SO3?H+??(1a) R is hydroxyl, alkyl, aryl, hetero-aryl, alkoxy, aryloxy or hetero-aryloxy, R1 is a divalent organic group which may have a heteroatom (O, N or S) containing substituent, or R1 may form a cyclic structure with R. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.
    Type: Grant
    Filed: September 27, 2007
    Date of Patent: May 5, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Koji Hasegawa, Masaki Ohashi
  • Patent number: 7527913
    Abstract: A photoresist composition includes about 4% to about 10% by weight of a photoresist resin, about 0.1% to about 0.5% by weight of a photoacid generator having a sulfonium-salt cationic group and a sulfonium-salt anionic group containing a carboxyl group as a hydrophilic site and a remainder of a solvent. The photoresist composition may form a photoresist pattern having a uniform profile.
    Type: Grant
    Filed: January 24, 2008
    Date of Patent: May 5, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Young-Gil Kwon, Young-Ho Kim, Do-Young Kim, Jae-Hee Choi, Se-Kyung Baek
  • Patent number: 7524614
    Abstract: A radiation-sensitive composition includes a radically polymerizable component and an iodonium borate initiator composition capable of generating radicals sufficient to initiate polymerization of the free radically polymerizable component upon exposure to imaging radiation. The iodonium borate composition includes a particular diaryliodonium borate compound having organic substituents to provide a sum of at least 6 carbon atoms on the iodonium cation phenyl rings. This composition can be applied to a suitable substrate to provide a negative-working imageable element with improved digital speed and good shelf life and that can be imaged to provide lithographic printing plates. The imaged elements can be developed either on-press or off-press using alkaline developers.
    Type: Grant
    Filed: May 26, 2006
    Date of Patent: April 28, 2009
    Assignee: Eastman Kodak Company
    Inventors: Ting Tao, Scott A. Beckley
  • Patent number: 7517633
    Abstract: A composition for forming a gap-filling material for lithography which, as a gap-filling material for lithography superior in planarization ability on a substrate having irregularities such as holes or trenches, causing no intermixing with a resist layer, and having a high dry etching rate as compared with the resist, is used in producing semiconductor devices by a method using the gap-filling material to cover the resist on the substrate having holes having an aspect ratio, defined as height/diameter, of 1 or more to transfer images onto the substrate by utilization of lithographic process, the composition being used to coat the substrate prior to the coating of the resist so as to planarize the substrate surface, and the composition being characterized by containing a polymer solution consisting of a polymer and a solvent.
    Type: Grant
    Filed: July 12, 2001
    Date of Patent: April 14, 2009
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Satoshi Takei, Ken-ichi Mizusawa, Yasuhisa Sone
  • Patent number: 7514199
    Abstract: Provided herein are hardmask compositions for resist underlayer films, wherein in some embodiments, the hardmask compositions include (a) a first polymer prepared by the reaction of a compound of Formula 1 ?wherein n is a number of 3 to 20, with a compound of Formula 2 (R)m—Si—(OCH3)4-m??(2) ?wherein R is a monovalent organic group and m is 0, 1 or 2; (b) a second polymer that includes at least one of the structures represented by Formulae 3-6; (c) an acid or base catalyst; and (d) an organic solvent. Further provided herein are methods for producing a semiconductor integrated circuit device using a hardmask composition according to an embodiment of the present invention. In addition, provided herein are semiconductor integrated circuit devices produced by a method embodiment of the invention.
    Type: Grant
    Filed: August 22, 2006
    Date of Patent: April 7, 2009
    Assignee: Cheil Industries, Inc.
    Inventors: Dong Seon Uh, Chang Il Oh, Do Hyeon Kim, Hui Chan Yun, Jin Kuk Lee, Irina Nam, Jong Seob Kim
  • Patent number: 7514203
    Abstract: Disclosed is a positive photoresist composition used for a liquid crystal display. The positive photoresist composition of the present invention includes 3 to 50% by weight of binder resin having a certain structure, 2 to 40% by weight of a photoactive compound and 10 to 94% by weight of an organic solvent. The positive photoresist composition according to the present invention may be useful to form a pattern for an organic insulator of a liquid crystal display, metal patterning, a bump, hole drilling and UV overcoat since it has good basic physical properties such as UV transmittance, film retention, pattern stability, chemical resistance and so on, as well as an excellent heat resistance.
    Type: Grant
    Filed: December 21, 2005
    Date of Patent: April 7, 2009
    Assignee: Samyangems Co., Ltd.
    Inventors: Bong-Seok Moon, Hyo-Jeong Kim, Jin-Gon Kim, Yang-Hyun Yoo, Min-Ji Kim, Mi-Kyeong Jeong, Kwon-Yil Yoo, Nak-Chil Jung, Seon-Ho Kim
  • Patent number: 7514201
    Abstract: A positive photosensitive composition comprising (A) an acid generator that generates an acid upon irradiation of an actinic ray or radiation, (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase solubility in an alkali developing solution, and (C) a specific basic compound.
    Type: Grant
    Filed: January 26, 2007
    Date of Patent: April 7, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Toru Fujimori
  • Patent number: 7514204
    Abstract: A resist composition comprises a polymer which increases its alkali solubility under the action of an acid as a base resin, and a copolymer comprising recurring units containing a sulfonic acid amine salt and recurring units containing at least one fluorine atom as an additive. The composition is suited for immersion lithography.
    Type: Grant
    Filed: October 23, 2007
    Date of Patent: April 7, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Wataru Kusaki, Yuji Harada, Takao Yoshihara
  • Patent number: 7504195
    Abstract: A photosensitive polymer which can form a fine circuit pattern by exacting with extreme UV and deep UV, and can improve a line width stability of a pattern by significantly reducing line edge roughness after developing, and a photoresist composition including the same are disclosed. The photosensitive polymer for extreme UV and deep UV includes a repeating unit represented by the following Formula 1, in Formula 1, R1 and R1? are independently a hydrogen atom, methyl group, or trifluoromethyl group, and R2 is wherein Ra and Rb are independently alkyl group of 1 to 10 carbon atoms, aryl group of 6 to 10 carbon atoms, or arylalkyl group of 7 to 12 carbon atoms, and can be connected together to form ring, and a and b are mol % of each repeating unit with respect to the total repeating unit constituting the photosensitive polymer, and are 1 to 99 mol % and 1 to 99 mol % respectively.
    Type: Grant
    Filed: August 9, 2007
    Date of Patent: March 17, 2009
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Deog-Bae Kim, Jae-Hyun Kim
  • Patent number: 7501221
    Abstract: There is provided a positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.
    Type: Grant
    Filed: February 2, 2006
    Date of Patent: March 10, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
  • Patent number: 7501222
    Abstract: A polymer including a monomer represented by the following Formula and a photoresist composition including the same are disclosed. The polymer and photoresist composition can improve the resolution and the process margin due to the low activation energy of the deprotection reaction of the alcohol ester group including saturated cyclic hydrocarbyl group, and also can produce fine photoresist patterns because they have a stable PEB(Post Exposure Baking) temperature sensitivity, and further, can improve the focus depth margin and the line edge roughness of the resist layer. In the above Formula, R* is a hydrogen or methyl group, R1 is saturated hydrocarbyl group of 1 to 5 carbon atoms, R is mono-cyclic or multi-cyclic homo or hetero saturated hydrocarbyl group of 3 to 50 carbon atoms, and n is an integer of at least 2.
    Type: Grant
    Filed: June 21, 2006
    Date of Patent: March 10, 2009
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jung-Youl Lee, Jae-Woo Lee, Jae-Hyun Kim
  • Patent number: 7498116
    Abstract: A resist composition includes: (A) a resin that includes: a repeating unit represented by a following formula (I), and a repeating unit represented by a following formula (II); and (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation: wherein the variables in the formulae are defined in the specification.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: March 3, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Shuji Hirano, Shinichi Sugiyama
  • Patent number: 7494762
    Abstract: Provided are a positive resist composition for immersion lithography, and a method for forming a resist pattern using the same, wherein the positive resist composition comprises a resin component (A) that increases its alkali solubility under action of an acid, an acid generator component (B) that generates an acid upon exposure, and a resin component (C) containing a constituent unit (c1) represented by the following Chemical Formula 1: wherein R1 is a hydrogen atom or a methyl group; R2 and R3 are each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; n is an integer of 0 to 3; and Z is an aliphatic cyclic group having 4 to 12 carbon atoms, having a fluorine atom and/or a fluorinated alkyl group as a substituent.
    Type: Grant
    Filed: October 12, 2007
    Date of Patent: February 24, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Makiko Irie, Yasuhiro Yoshii
  • Patent number: 7494763
    Abstract: The present invention provides a polyhydric phenol compound represented by the formula (I): wherein at least one selected from R1, R2, R3, R4, and R5 is a group represented by the formula (II): wherein X1, X2, X3 and X4 each independently represent a hydrogen atom or a C1-C4 alkyl group, n represents an integer of 0 to 3, Z1 represents a C1-C6 alkyl group or a C3-C12 cycloalkyl group, and ring Y represents an alicyclic hydrocarbon group, and the others are hydrogen atoms, and a chemically amplified resist composition containing the same.
    Type: Grant
    Filed: October 22, 2007
    Date of Patent: February 24, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ichiki Takemoto, Nobuo Ando, Junji Shigematsu
  • Patent number: 7494760
    Abstract: A photoacid generator has formula (1) wherein R is H, F, Cl, nitro, alkyl or alkoxy, n is 0 or 1, m is 1 or 2, r is an integer of 0-4, and r? is an integer of 0-5. A chemically amplified resist composition comprising the photoacid generator has advantages including a high resolution, focus latitude, long-term PED dimensional stability, and a satisfactory pattern profile shape. When the photoacid generator is combined with a resin having acid labile groups other than those of the acetal type, resolution and top loss are improved. The composition is suited for deep UV lithography.
    Type: Grant
    Filed: June 1, 2007
    Date of Patent: February 24, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Katsuya Takemura, Akihiro Seki
  • Patent number: 7491483
    Abstract: A polymer is composed of recurring units of hydroxyvinylnaphthalene, (meth)acrylic units having a lactone ring fused to a bridged ring, and (meth)acrylic units having acid labile groups. A positive resist composition comprising the polymer as a base resin, when exposed to high-energy radiation and developed, exhibits a high sensitivity, a high resolution, and a minimal line edge roughness due to controlled swell during development.
    Type: Grant
    Filed: March 5, 2007
    Date of Patent: February 17, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takeshi Kinsho, Takanobu Takeda
  • Patent number: 7491484
    Abstract: In a photoresist composition and a method of forming a pattern using the same, the photoresist composition includes about 0.1 to about 0.5 percent by weight of a photoacid generator including a positively charged sulfonium ion and a negatively charged sulfonate ion having a hydrophilic carboxylic group, about 4 to about 10 percent by weight of a resin, and a solvent.
    Type: Grant
    Filed: October 10, 2007
    Date of Patent: February 17, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Young-Gil Kwon, Do-Young Kim, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim
  • Patent number: 7491485
    Abstract: This resist composition according to the present invention includes 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 an acid upon exposure, wherein the acid generator component (B) includes an acid generator (B1) represented by a general formula (b1-6-1) shown below and an acid generator (B2) represented by a general formula (b1-6-2) shown below: (wherein, R40 represents a hydrogen atom or an alkyl group; R41 represents a halogen atom, a halogenated alkyl group, an alkyl group, an acetyl group, a carboxyl group or a hydroxyalkyl group; R42 and R43 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an acetyl group, an alkoxy group, a carboxyl group or a hydroxyalkyl group; n0 to n3 each independently represents an integer of 0 to 3, with the proviso that n0+n1 is 5 or less; R13 each independently represents a linear or branched alkyl group of 1 to 10 carbon
    Type: Grant
    Filed: May 20, 2008
    Date of Patent: February 17, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Komei Hirahara
  • Patent number: 7488568
    Abstract: A resist composition including a base component (A) and an acid-generator component (B), the acid-generator component (B) including an acid generator (B1) including a compound represented by general formula (b1-8) shown below (wherein R401 represents an acid dissociable, dissolution inhibiting group; R41 to R43 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an acetyl group, an alkoxy group, a carboxy group or a hydroxyalkyl group; Q represents a divalent linking group or a single bond; and X? represents an anion) or an acid generator (B1?) including a compound represented by general formula (b1-9) shown below (wherein R402 and R403 each independently represents a hydrogen atom, an alkyl group or a halogenated alkyl group; R404 represents an alkyl group or a halogenated alkyl group, wherein R403 and R404 may be bonded to each other to form a ring structure; and X? represents an anion).
    Type: Grant
    Filed: April 1, 2008
    Date of Patent: February 10, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takeshi Iwai, Hideo Hada, Masaru Takeshita, Akiya Kawaue, Keita Ishiduka, Hiroaki Shimizu, Kyoko Ohshita, Tsuyoshi Nakamura, Komei Hirahara, Yuichi Suzuki, Takehiro Seshimo, Kensuke Matsuzawa
  • Patent number: 7488565
    Abstract: Novel positive-working photoresist compositions are disclosed. The monomers of the base resin of the resist contain diamondoid-containing pendant groups higher than adamantane in the polymantane series; for example, diamantane, triamantane, tetramantane, pentamantane, hexamantane, etc. The diamondoid-containing pendant group may have hydrophilic-enhancing substituents such as a hydroxyl group, and may contain a lactone group. Advantages of the present compositions include enhanced resolution, sensitivity, and adhesion to the substrate.
    Type: Grant
    Filed: January 23, 2004
    Date of Patent: February 10, 2009
    Assignee: Chevron U.S.A. Inc.
    Inventors: Shenggao Liu, Jeremy E. Dahl, Robert M. Carlson
  • Patent number: 7488567
    Abstract: A polymer comprising recurring units of formula (1) wherein R1 is F or fluoroalkyl, R2 is alkylene or fluoroalkylene, and R3 is an acid labile group and having a Mw of 1,000-500,000 is used to formulate a resist composition, which is processed by the lithography involving ArF exposure and offers many advantages including resolution, minimal line edge roughness, etch resistance, and minimal surface roughness after etching. The composition performs well when processed by the ArF immersion lithography with liquid interposed between the projection lens and the wafer.
    Type: Grant
    Filed: May 25, 2006
    Date of Patent: February 10, 2009
    Assignees: Panasonic Corporation, Central Glass Co., Ltd., Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Kazuhiko Maeda, Haruhiko Komoriya, Michitaka Ootani