Halogen Compound Containing Patents (Class 430/925)
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Sulfonium salt, polymer, method for producing the polymer, resist composition and patterning process
Patent number: 8691490Abstract: There is disclosed a sulfonium salt represented by the following general formula (1). In the formula, X and Y each represents a group having a polymerizable functional group; Z represents a divalent hydrocarbon group having 1 to 33 carbon atoms optionally containing a hetero atom; R1 represents a divalent hydrocarbon group having 1 to 36 carbon atoms optionally containing a hetero atom; and R2 and R3 each represents a monovalent hydrocarbon group having 1 to 30 carbon atoms optionally containing a hetero atom or R2 and R3 may be bonded with each other to form a ring together with a sulfur atom in the formula. There can be provided a sulfonium salt usable as a resist composition providing high resolution and excellent in LER in photolithography using a high energy beam such as an ArF excimer laser, an EUV light and an electron beam as a light source, a polymer obtained from the sulfonium salt, a resist composition containing the polymer and a patterning process using the resist composition.Type: GrantFiled: January 25, 2011Date of Patent: April 8, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Satoshi Watanabe, Youichi Ohsawa, Keiichi Masunaga, Takeshi Kinsho -
Patent number: 8685619Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, A13, A14, X12, R23, R24, R25, X21 and Z1+ are defined in the specification.Type: GrantFiled: July 18, 2012Date of Patent: April 1, 2014Assignee: Sumitomo Chemcial Company, LimitedInventors: Koji Ichikawa, Yuichi Mukai, Satoshi Yamamoto
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Patent number: 8663900Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, A13, A14, X12, RII1, RII2, LII1, YII1, RII3, RII4, RII5, RII6, RII7, n, s and RII8 are defined in the specification.Type: GrantFiled: July 18, 2012Date of Patent: March 4, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
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Patent number: 8663899Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator, wherein R1, A1, R2, Rb1, Rb2, Lb1, ring Wb1, Rb3, Rb4, and Z1+ are defined in the specification.Type: GrantFiled: July 18, 2012Date of Patent: March 4, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Takashi Hiraoka, Hiromu Sakamoto
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Patent number: 8652754Abstract: 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, Q1 and Q2, L1, ring W, Rf1 and Rf2, n and Z+are defined in the specification.Type: GrantFiled: July 18, 2012Date of Patent: February 18, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Takashi Hiraoka, Mitsuyoshi Ochiai
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Patent number: 8628909Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.Type: GrantFiled: September 14, 2012Date of Patent: January 14, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8628908Abstract: A chemically amplified resist composition is provided comprising (A) a specific tertiary amine compound, (B) a specific acid generator, (C) a base resin having an acidic functional group protected with an acid labile group, which is substantially insoluble in alkaline developer and turns soluble in alkaline developer upon deprotection of the acid labile group, and (D) an organic solvent. The resist composition has a high resolution, improved defect control in the immersion lithography, and good shelf stability.Type: GrantFiled: February 28, 2012Date of Patent: January 14, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Tomohiro Kobayashi, Masayoshi Sagehashi, Takeshi Nagata, Youichi Ohsawa, Ryosuke Taniguchi
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Patent number: 8628910Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.Type: GrantFiled: September 14, 2012Date of Patent: January 14, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8623584Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.Type: GrantFiled: September 14, 2012Date of Patent: January 7, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8617790Abstract: A photoresist composition comprising (A) a resin which has an acid-labile group-containing structural unit and a lactone ring-containing structural unit, and (B) a salt represented by formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, n represents 0 or 1, L1 represents a single bond or a C1-C10 alkanediyl group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, provided that L1 is not a single bond when n is 0, R1 represents a hydroxy group or a hydroxy group protected by a protecting group, and Z+ represents an organic cation.Type: GrantFiled: April 17, 2012Date of Patent: December 31, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
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Patent number: 8617786Abstract: The present invention relates to compositions comprising poly-oxycarbosilane and methods for using the compositions in step and flash imprint lithography. The imprinting compositions comprise a poly-oxycarbosilane polymer, a silanol, a reaction initiator and optionally a pore generator.Type: GrantFiled: February 11, 2011Date of Patent: December 31, 2013Assignee: International Business Machines CorporationInventors: Richard Anthony Dipietro, Geraud Jean-Michel Dubois, Robert Dennis Miller, Ratnam Sooriyakumaran
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Patent number: 8614047Abstract: Provided are novel symmetrical and asymmetrical bifunctional photodecomposable bases (PDBs) with dicarboxylate anion groups that show increased imaging performance. Also provided are photoresist compositions prepared with the bifunctional dicarboxylated PDBs and lithography methods that use the photoresist compositions of the present invention.Type: GrantFiled: August 26, 2011Date of Patent: December 24, 2013Assignees: International Business Machines Corporation, JSR CorporationInventors: Ramakrishnan Ayothi, William D. Hinsberg, Sally A. Swanson, Gregory M. Wallraff
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Patent number: 8609889Abstract: The photoacid generator produces a sulfonic acid which has a bulky cyclic structure in the sulfonate moiety and a straight-chain hydrocarbon group and thus shows a controlled acid diffusion behavior and an adequate mobility. The PAG is fully compatible with a resin to form a resist composition which performs well during the device fabrication process and solves the problems of resolution, LWR, and exposure latitude.Type: GrantFiled: July 1, 2010Date of Patent: December 17, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
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Patent number: 8609891Abstract: New photoacid generator compounds are provided that comprise a nitrogen-base functional component of the structure —C(?O)N<. Photoresist compositions also are provided that comprise one or more PAGs of the invention.Type: GrantFiled: April 27, 2011Date of Patent: December 17, 2013Assignee: Rohm and Haas Electronic Materials LLCInventors: Young Cheol Bae, Thomas Cardolaccia, Yi Liu
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Patent number: 8597869Abstract: A sulfonium salt of a naphthyltetrahydrothiophenium cation having a fluoroalkoxy chain with a specific anion is provided. The sulfonium salt is used as a photoacid generator to form a resist composition which when processed by immersion lithography, offers advantages of restrained dissolution in the immersion water and less pattern dependence or dark/bright bias.Type: GrantFiled: September 23, 2011Date of Patent: December 3, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayoshi Sagehashi, Youichi Ohsawa, Koji Hasegawa, Takeshi Kinsho, Tomohiro Kobayashi
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Patent number: 8586281Abstract: A positive resist composition including: a base component; and a sensitizer which a polymeric compound having a core portion that includes a hydrocarbon group or a heterocycle of two or more valences and at least one arm portion bonded to the core portion and represented by formula (1), and a polymeric compound having a core portion including a polymer having a molecular weight of 500 to 20,000 and at least one arm portion bonded to the core portion and represented by formula (1); and either the base component includes a resin component that generates acid upon exposure and exhibits increased solubility in an alkali developing solution under action of acid, or the positive resist composition further contains an acid generator component including a compound that generates acid upon exposure: —(X)—Y??(1) in which X represents a divalent linking group having an acid dissociable group; and Y represents a polymer chain.Type: GrantFiled: June 8, 2011Date of Patent: November 19, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Jun Iwashita, Masahito Yahagi, Kenri Konno, Isamu Takagi
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Patent number: 8580486Abstract: There is provided an acid having a fluorine-containing carbanion structure or a salt having a fluorine-containing carbanion structure, which is represented by the following general formula (1). By using a photoacid generator for chemically amplified resist materials that generates this acid, it is possible to provide a photoacid generator which has a high sensitivity to the ArF excimer laser light or the like, of which acid (photo generated acid) to be generated has a sufficiently high acidity, and which has a high dissolution in resist solvent and a superior compatibility with resin, and a resist material containing such a photoacid generator.Type: GrantFiled: March 10, 2009Date of Patent: November 12, 2013Assignee: Central Glass Company, LimitedInventors: Masashi Nagamori, Satoru Narizuka, Susumu Inoue, Takashi Kume
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Patent number: 8574817Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1), (2) or (3) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a reduced acid diffusion rate, and forms a pattern with good profile, minimal edge roughness, and etch resistance. In formula (1), R1, R2, R5, R6, R8, and R9 are alkyl, aryl, or alkenyl, R3, R4, R7, R10, and R11 are hydrogen, alkyl, alkoxy, acyloxy, halogen, cyano, nitro, hydroxyl or trifluoromethyl, M is methylene or ethylene, R is a single bond or linking group.Type: GrantFiled: September 13, 2012Date of Patent: November 5, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Koji Hasegawa
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Patent number: 8574811Abstract: A resist composition contains; a resin having a structural unit derived from a compound represented by the formula (a); and an acid generator. wherein R1 represents a hydrogen atom or a methyl group; R2 represents an optionally substituted C1 to C18 aliphatic hydrocarbon group; A1 represents an optionally substituted C1 to C6 alkanediyl group or a group represented by the formula (a-g1); wherein s represents 0 or 1; A10 and A12 independently represent an optionally substituted C1 to C5 aliphatic hydrocarbon group; A11 represents a single bond or an optionally substituted C1 to C5 aliphatic hydrocarbon group; X10 and X11 independently represents an oxygen atom, a carbonyl group, a carbonyloxy group or an oxycarbonyl group; provided that a total number of the carbon atom of A10, A11, A12, X10 and X11 is 6 or less.Type: GrantFiled: August 30, 2011Date of Patent: November 5, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuro Masuyama, Satoshi Yamamoto, Koji Ichikawa
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Patent number: 8557498Abstract: A photosensitive resin composition is used that comprises a photosensitive silicone having a styryl group as a photosensitive group, and a photopolymerization initiator having a specific structure. As a result, a photosensitive resin composition capable of being cured in air by photopolymerization that is preferable for use as a buffer coat material or rewiring layer of an LSI chip, a method for forming a cured relief pattern using this photosensitive resin composition, and a semiconductor device comprising the cured relief pattern are provided.Type: GrantFiled: March 25, 2008Date of Patent: October 15, 2013Assignee: Asahi Kasei E-Materials CorporationInventor: Tomohiro Yorisue
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Patent number: 8557500Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, L2 represents a single bond or a C1-C6 alkanediyl group in which one or more —CH2— can be replaced by —O— or —CO—, Y represents a C3-C18 alicyclic hydrocarbon group which can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O—, —CO— or —SO2—, and Z+ represents an organic counter ion.Type: GrantFiled: February 28, 2012Date of Patent: October 15, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Hiromu Sakamoto, Takahiro Yasue
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Patent number: 8546059Abstract: The present invention provides a photoresist composition comprising a resin, an acid generator and a compound represented by the formula (C1): wherein Rc1 represents an aromatic group which can have one or more substituents, Rc2 and Rc3 independently each represent a hydrogen atom, an aliphatic hydrocarbon group which can have one or more substituents or an aromatic group which can have one or more substituents, Rc4 and Rc6 independently each represent a hydrogen atom or an aliphatic hydrocarbon group which can have one or more substituents, or Rc4 and Rc6 are bonded each other to form an alkanediyl group, Rc5 represents an aliphatic hydrocarbon group which can have one or more substituents or an amino group which can have one or two substituents, Rc7 represents a hydrogen atom or an aliphatic hydrocarbon group which can have one or more substituents, or Rc5 and Rc7 are bonded each other to form an alkanediyl group.Type: GrantFiled: November 24, 2010Date of Patent: October 1, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Takayuki Miyagawa, Mitsuhiro Hata
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Patent number: 8541161Abstract: Provided are an actinic ray-sensitive or radiation-sensitive resin composition; a resist film using the composition; and a pattern forming method. The actinic ray-sensitive or radiation-sensitive resin composition includes (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, the resin containing a repeating unit represented by formula (I), a repeating unit represented by formula (II) and a repeating unit represented by formula (III), and (B) a compound capable of generating a fluorine atom-containing acid upon irradiation with an actinic ray or radiation: wherein each of R1 and R11 independently represents a hydrogen atom or an alkyl group which may have a substituent, and R12 represents a phenyl group which may have a substituent.Type: GrantFiled: March 23, 2010Date of Patent: September 24, 2013Assignee: FUJIFILM CorporationInventors: Kana Fujii, Shuji Hirano, Shinki Yamada, Toru Fujimori
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Resist composition, method of forming resist pattern, compound and acid generator including the same
Patent number: 8541157Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under the action of acid and an acid-generator component (B) which generates acid upon exposure, wherein the acid-generator component (B) includes an acid generator (B1) composed of a compound having a base dissociable group within a cation moiety.Type: GrantFiled: September 25, 2009Date of Patent: September 24, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Sho Abe -
Patent number: 8535869Abstract: A sulfonium salt of a naphthylsulfonium cation having a hydrophilic phenolic hydroxyl group or ethylene glycol chain with a specific anion is provided. The sulfonium salt is used as a photoacid generator to form a resist composition which when processed by immersion lithography, offers advantages of restrained dissolution in the immersion water and less pattern dependence or dark-bright difference.Type: GrantFiled: August 22, 2011Date of Patent: September 17, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Masayoshi Sagehashi, Tomohiro Kobayashi
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Patent number: 8530135Abstract: The present invention provides a photoresist composition comprising a resin 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, an acid generator and a compound represented by the formula (I): wherein Z1 represents a C7-C20 alkylene group, a C3-C20 divalent saturated cyclic group or a divalent group formed by combining at least one C1-C6 alkylene group with at least one C3-C20 divalent saturated cyclic group.Type: GrantFiled: September 22, 2010Date of Patent: September 10, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Soon Shin Kim, Isao Yoshida, Koji Ichikawa
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Patent number: 8524440Abstract: The present invention provides a photoresist composition comprising a resin which comprises a structural unit represented by the formula (I): wherein Q1 and Q2 independently represent a fluorine atom etc., U represents a C1-C20 divalent hydrocarbon group etc., X1 represents —O—CO— etc., and A+ represents an organic counter ion, and a compound represented by the formula (D?): wherein R51, R52, R53 and R54 independently represent a C1-C20 alkyl group etc., and A11 represents a C1-C36 saturated cyclic hydrocarbon group which may have one or more substituents and which may contain one or more heteroatoms.Type: GrantFiled: January 3, 2011Date of Patent: September 3, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Yuko Yamashita, Nobuo Ando
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Patent number: 8507180Abstract: Disclosed are a chemically amplified positive-type photoresist composition for a thick film, a chemically amplified dry film for a thick film, and a method for producing a thick film resist pattern, all of which are capable of obtaining a satisfactory resist pattern with high sensitivity even on a substrate having a portion formed of copper on an upper surface thereof. The chemically amplified positive-type photoresist composition for a thick film comprises component (A) which includes at least one compound capable of producing an acid upon irradiation with an actinic ray or radiation, and component (B) which includes at least one resin whose alkali solubility increases by the action of an acid, in which the component (A) includes an onium fluorinated alkyl fluorophosphate having a specific structure.Type: GrantFiled: October 18, 2007Date of Patent: August 13, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yasushi Washio, Kazuhide Uno, Koichi Misumi, Takahiro Senzaki, Koji Saito, Nobuko Ohgake
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Patent number: 8501382Abstract: There are disclosed sulfonic acid precursor compositions, as are methods of using these compositions in, for example, photolithography. Other embodiments are also disclosed.Type: GrantFiled: February 19, 2010Date of Patent: August 6, 2013Assignee: The Research Foundation of State Univ. of New YorkInventor: Robert L. Brainard
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Patent number: 8501384Abstract: A positive resist composition comprising a polymer having a tetrahydrobenzocycloheptane-substituted secondary or tertiary carboxyl group ester as an acid labile group exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal edge roughness after exposure, a significant effect of suppressing acid diffusion rate, and improved etching resistance.Type: GrantFiled: January 7, 2011Date of Patent: August 6, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Takeru Watanabe, Seiichiro Tachibana
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Patent number: 8470513Abstract: A radiation-sensitive resin composition includes a polymer that includes at least one repeating unit (i) selected from a repeating unit shown by a formula (1), (2), and (3); and a repeating unit (ii) shown by a formula (4). R1 represents a hydrogen atom or a methyl group. Each R2 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms. p is an integer from 0 to 3, and q is an integer from 1 to 3, and p+q?5. A chemically-amplified positive-tone resist film that is sensitive to extreme ultraviolet rays (EUV) can be formed using the radiation-sensitive resin composition.Type: GrantFiled: September 23, 2011Date of Patent: June 25, 2013Assignee: JSR CorporationInventors: Kota Nishino, Ken Maruyama, Daisuke Shimizu, Toshiyuki Kai
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Patent number: 8460851Abstract: A salt represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents *—CO—O-La- or *—CH2—O-Lb-, * represents a binding position to —C(Q1)(Q2)-, La and Lb independently represent a C1-C15 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, ring W1 represents a C2-C36 nitrogen-containing heterocyclic group in which one or more —CH2— can be replaced by —O—, and Z1? represents an organic counter ion.Type: GrantFiled: January 6, 2011Date of Patent: June 11, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Koji Ichikawa
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Patent number: 8450041Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes (A) a compound capable of generating a specific acid having a norbornyl structure upon irradiation with an actinic ray or radiation, and (B) a resin capable of increasing the dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure on the resin side chain through a linking group, and a pattern forming method uses the composition.Type: GrantFiled: January 15, 2010Date of Patent: May 28, 2013Assignee: FUJIFILM CorporationInventor: Shuhei Yamaguchi
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Patent number: 8440384Abstract: A compound has a partial structure shown by a following formula (1), wherein R1 represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 8 carbon atoms, R2 represents a substituted or unsubstituted hydrocarbon group having 1 to 8 carbon atoms, Rf represents a fluorine atom or a perfluoroalkyl group having 1 to 4 carbon atoms, L represents an integer from 0 to 4, n represents an integer from 0 to 10, and m represents an integer from 1 to 4.Type: GrantFiled: April 14, 2010Date of Patent: May 14, 2013Assignee: JSR CorporationInventors: Takuma Ebata, Tomoki Nagai
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Patent number: 8435717Abstract: A sulfonic acid onium salt represented by the following formula (1) can be used as a superior radiosensitive acid generator for resist compositions. It is possible to form a good pattern by using a resist composition containing this sulfonic acid onium salt. In formula (1), R1 represents a monovalent organic group, and Q+ represents a sulfonium cation or iodonium cation.Type: GrantFiled: February 14, 2008Date of Patent: May 7, 2013Assignee: Central Glass Company, LimitedInventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
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Patent number: 8431324Abstract: A radiation-sensitive resin composition includes a resin, a radiation-sensitive acid generator, an acid diffusion controller, and a mixed solvent. The radiation-sensitive acid generator includes a compound (I) shown by a following general formula (I). The mixed solvent includes about 50 mass % to about 90 mass % of propylene glycol monomethyl ether acetate, wherein M+ represents a sulfonium cation or an iodonium cation, R represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms, Rf represents a fluorine atom or a perfluoroalkyl group having 1 to 4 carbon atoms, n represents an integer from 1 to 10, and m represents an integer from 1 to 4.Type: GrantFiled: May 7, 2010Date of Patent: April 30, 2013Assignee: JSR CorporationInventors: Tsutomu Shimokawa, Takuma Ebata
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Patent number: 8426113Abstract: The present invention provides chemically amplified silsesquioxane polymers for preparing masks using e-beam lithography. The silsesquioxane polymers have reactive sidechains that in the presence of an acid undergo acid catalyzed rearrangement to generate reactive functionalities that crosslink to form Si—O—Si bonds. The reactive side-chains comprise ?- and ?-substituted alkyl groups bound to the silicon of the silsesquioxane polymer. The substituent of the ?- and ?-substituted alkyl group is an electron withdrawing group. Resists generated with the chemically amplified silsesquioxane polymers of the present invention and imaged with e-beams have resolution of ?60 nm line/space.Type: GrantFiled: August 13, 2010Date of Patent: April 23, 2013Assignee: International Business Machines CorporationInventors: Luisa Dominica Bozano, Blake W. Davis, Alshakim Nelson, Jitendra Singh Rathore, Linda Karin Sundberg
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Patent number: 8426106Abstract: A Photoresist composition comprising a polymer comprising a structural unit derived from a compound represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, R2 represents a C6-C12 aromatic hydrocarbon group which can have one or more substituents, R3 represents a cyano group or a C1-C12 hydrocarbon group which can have one or more substituents and which can contain one or more heteroatoms, A1 represents a single bond, —(CH2)g—CO—O—* or —(CH2)h—O—CO—(CH2)i—CO—O—* wherein g, h and i each independently represent an integer of ?1 to 6 and * represents a binding position to the nitrogen atom, a resin 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, and an acid generator.Type: GrantFiled: October 12, 2010Date of Patent: April 23, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuro Masuyama, Kazuhiko Hashimoto, Junji Shigematsu
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Patent number: 8420299Abstract: It is therefore an object of the present invention to provide a forming method for a resist pattern to reduce a resist residue in forming the resist pattern on a step whose gradient angle is equal to 90 degrees or more. A forming method for a resist pattern to reduce a resist residue on a step is provided, the method comprising: forming resist film with coating resist containing photo-acid-generator on a step formed on a substrate, where gradient angle of the step is equal to 90 degrees or more, exposing said resist film and generating acid from said photo-acid-generator.Type: GrantFiled: August 6, 2008Date of Patent: April 16, 2013Assignee: TDK CorporationInventors: Hisayoshi Watanabe, Susumu Aoki
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Patent number: 8415081Abstract: The present invention discloses a photosensitive resin composition which comprises (A) a compound having a molecule with at least one thiirane ring and a total number of a thiirane ring and/or an epoxy ring of at least 2 in the molecule, and (B) a photo acid generator, said composition having a refractive index of at least 1.6, and a method of obtaining a high refractive index periodical structure which comprises subjecting the photosensitive resin composition to photolithography.Type: GrantFiled: June 17, 2004Date of Patent: April 9, 2013Assignees: Cornell Research Foundation, Inc., Hitachi Chemical Co., Ltd.Inventors: Christopher K. Ober, Yasuharu Murakami
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Patent number: 8415085Abstract: 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: GrantFiled: May 23, 2012Date of Patent: April 9, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
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Patent number: 8367299Abstract: A resist composition including: a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid; and an acid-generator component (B) which generates acid upon exposure, wherein said acid-generator component (B) comprises an acid generator (B1) including a compound represented by general formula (b1-11) shown below: wherein R7? to R9? each independently represent an aryl group or an alkyl group, wherein two of R7? to R9? may be bonded to each other to form a ring with the sulfur atom, and at least one of R7? to R9? represents a substituted aryl group having a group represented by general formula (I) shown below as a substituent; X? represents an anion; and Rf represents a fluorinated alkyl group.Type: GrantFiled: September 15, 2011Date of Patent: February 5, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehiro Seshimo, Tsuyoshi Nakamura, Naoto Motoike, Hiroaki Shimizu, Kensuke Matsuzawa, Hideo Hada
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Patent number: 8349535Abstract: According to one embodiment, an actinic ray-sensitive or radiation-sensitive resin composition includes (A) a resin containing the repeating units of formulae (I), (II) and (III) that when acted on by an acid, becomes soluble in an alkali developer, and (B) a compound that when irradiated with actinic rays or radiation, generates a fluorine-containing acid, wherein each of R1 independently represents a hydrogen atom or an optionally substituted methyl group, R2 represents a halogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group or an optionally substituted aralkyl group, and n is an integer of 0 to 5, provided that when n is 2 or greater, multiple R2s may be identical to or different from each other.Type: GrantFiled: September 30, 2010Date of Patent: January 8, 2013Assignee: FUJIFILM CorporationInventors: Kana Fujii, Takamitsu Tomiga, Toru Tsuchihashi, Kazuyoshi Mizutani, Jiro Yokoyama, Shinichi Sugiyama, Shuji Hirano, Toru Fujimori
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Patent number: 8349533Abstract: A resist lower-layer composition configured to be used by a multi-layer resist method used in lithography to form a layer lower than a photoresist layer acting as a resist upper layer film. The resist lower-layer composition is insoluble or poorly-soluble in an alkaline developer after formation of the lower layer, and the resist lower-layer composition comprises, at least, a thermal acid generator for generating an acid by heating at a temperature of 100° C. or higher.Type: GrantFiled: October 20, 2009Date of Patent: January 8, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Jun Hatakeyama, Takeru Watanabe, Takeshi Kinsho
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Patent number: 8338074Abstract: It is intended to provide the following resin composition for stereolithography which is superior in storage stability and aging stability during operation, shows no increase in viscosity upon prolonged storage, has a high light-curing sensitivity and, therefore, makes it possible to produce, upon photo irradiation, an object by stereolithography, which is superior in dimensional accuracy, fabricating accuracy, water resistance, moisture resistance and mechanical properties at a high fabricating speed and a high productivity.Type: GrantFiled: June 24, 2004Date of Patent: December 25, 2012Assignees: CMET Inc., San-Apro Ltd.Inventors: Takashi Ito, Tsuneo Hagiwara, Hideki Kimura, Masashi Date, Jiro Yamamoto
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Patent number: 8338077Abstract: This invention relates to new photoacid generator compounds and photoresist compositions that comprise such compounds. In particular, the invention relates to photoacid generator compounds that comprise a multi cyclic lactone moiety.Type: GrantFiled: June 22, 2010Date of Patent: December 25, 2012Assignee: Rohm and Haas Electronic Materials LLCInventors: Mingqi Li, Cheng-Bai Xu, Emad Aqad, Cong Liu
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Patent number: 8334088Abstract: Linear or branched functionalized polycarbosilanes having an absorbance less than 3.0 ?m?1 at 193 nm and a relatively high refractive index are provided. The functionalized polycarbosilanes contain at least one pendant group that is acid labile or aqueous base soluble. Also disclosed are photoresists formulations containing the functionalized polycarbosilanes that are suitable for use in lithography, e.g., immersion lithography.Type: GrantFiled: November 3, 2010Date of Patent: December 18, 2012Assignee: International Business Machines CorporationInventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong
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Patent number: 8298746Abstract: The present invention provides a chemically amplified resist composition comprising: a resin (A) which itself is insoluble or poorly soluble in an aqueous alkali solution but becomes soluble in an aqueous alkali solution by the action of an acid and which comprises a structural unit having an acid-labile group in a side chain and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X1 represents an unsubstituted or substituted C3-C30 cyclic hydrocarbon group having —COO— and k represents an integer of 1 to 4, a resin (B) which comprises a structural unit represented by the formula (II): wherein R2 represents a hydrogen atom, a methyl group or a trifluoromethyl group, and an acid generator.Type: GrantFiled: June 24, 2009Date of Patent: October 30, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Junji Shigematsu, Kunishige Edamatsu, Takayuki Miyagawa, Akira Kamabuchi
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Patent number: 8288078Abstract: A photosensitive resin composition is provided that is highly safe, provides a coating film having superior uniformity, can improve the curing density of the cured resin pattern, and is capable of forming a micro resist pattern having a large film thickness and a high aspect ratio with high sensitivity and high resolving ability. According to a photosensitive resin composition including, in addition to an onium fluorinated alkyl fluorophosphate based cation polymerization initiator having a specific structure, a specified solvent or a specified sensitizing agent as essential components, a coating film having superior uniformity, can improve the curing density of the cured resin pattern, and also is capable of forming a micro resist pattern having a large film thickness and a high aspect ratio with high sensitivity and high resolving ability.Type: GrantFiled: January 11, 2008Date of Patent: October 16, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takahiro Senzaki, Koichi Misumi, Atsushi Yamanouchi, Koji Saito
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Patent number: 8247160Abstract: A resist composition including a base component that exhibits changed solubility in an alkali developing solution under the action of acid, and an acid generator consisting of a compound represented by general formula (b1). In formula (b1), Y1 represents a fluorinated alkylene group of 1 to 4 carbon atoms, X represents an aliphatic cyclic group of 3 to 30 carbon atoms, R11? to R13? each represents an aryl group or alkyl group, provided that at least one of R11? to R13? is an aryl group having a substituent represented by general formula (b1-0), and two alkyl groups among R11? to R13? may be bonded to each other to form a ring with the sulfur atom in the formula. In formula (b1-0), R52 represents a chain-like or cyclic hydrocarbon group, and f and g each represents 0 or 1.Type: GrantFiled: July 13, 2009Date of Patent: August 21, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Akiya Kawaue, Hiroaki Shimizu, Tsuyoshi Nakamura