Sulfur In Heterocyclic Ring Patents (Class 430/922)
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Patent number: 9040220Abstract: A resist composition including a base component which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component which generates acid upon exposure, the acid-generator including an acid generator consisting of a compound represented by general formula (b1-1) shown below: In which RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).Type: GrantFiled: March 2, 2012Date of Patent: May 26, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
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Patent number: 9034556Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) including an acid generator (B1) consisting of a compound represented by general formula (b1-1) shown below: wherein RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).Type: GrantFiled: December 18, 2008Date of Patent: May 19, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
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Patent number: 9029070Abstract: There are provided a method of forming a resist pattern includes: a step (1) in which a resist composition containing a base component (A) that generates base upon exposure and exhibits increased solubility in an alkali developing solution by the action of acid is applied to a substrate to form a resist film; a step (2) in which the resist film 2 is subjected to exposure; a step (3) in which baking is conducted after the step (2); and a step (4) in which the resist film 2 is subjected to an alkali development, thereby forming a negative-tone resist pattern in which the unexposed portion 2b of the resist film 2 has been dissolved and removed, and the resist composition used in the step (1).Type: GrantFiled: November 2, 2012Date of Patent: May 12, 2015Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito
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Patent number: 9005871Abstract: Compounds of the formula (I), wherein Ar1 is for example phenylene or biphenylene both unsubstituted or substituted; Ar2 and Ar3 are for example independently of each other phenyl, naphthyl, biphenylylyl or heteroaryl, all optionally substituted; or Ar1 and Ar2 for example together with a direct bond, O, S or (CO), form a fused ring system; R is for example hydrogen, C3-C30cycloalkyl or C1-C18alkyl; and R1, R2 and R3 independently of each other are for example C1-C10haloalkyl; are effective photoacid generators (PAG).Type: GrantFiled: October 8, 2009Date of Patent: April 14, 2015Assignee: BASF SEInventors: Hitoshi Yamato, Toshikage Asakura, Yuichi Nishimae
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Patent number: 9005872Abstract: A resist composition including a base component (A) which exhibits changed solubility in a developing solution under action of acid, a basic-compound component (C) and an acid-generator component (B) which generates acid upon exposure, the component (B) including a compound represented by formula (b1), and the component (C) including at least one compound represented by formulas (c1) to (c3) (wherein Z1 represents a ring skeleton-containing hydrocarbon group, Q1 represents a divalent linking group containing oxygen, Y1 represents a fluorinated alkylene group, M+ represents an organic cation, R1 represents a fluorinated alkyl group or a hydrocarbon group, L1+ and L2+ represents a sulfonium or an iodonium, Z2 represents a hydrogen atom or a hydrocarbon group, Y2 represents a single bond or a divalent linking group containing no fluorine, R2 represents an organic group, Y3 represents an alkylene group or an arylene group; and Rf represents a fluorine-containing hydrocarbon group).Type: GrantFiled: February 16, 2012Date of Patent: April 14, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroaki Shimizu, Sho Abe, Hideto Nito
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Patent number: 8993212Abstract: A resist composition according to the present invention includes at least a base resin, a photoacid generator and a solvent, wherein the photoacid generator comprises a fluorine-containing sulfonic acid salt of the following general formula (4). In the formula, X independently represents a hydrogen atom or a fluorine atom; n represents an integer of 1 to 6; R1 represents a hydrogen atom, or an alkyl, alkenyl, oxoalkyl, aryl or aralkyl group; any of hydrogen atoms on carbons in R1 may be substituted with a substituent; R2 represents RAO or RBRCN; and A represents a divalent group. This fluorine-containing sulfonic acid salt can serve as a photoacid generator having high solubility in a resist solvent and thus can suitably be used for a resist composition such that the resist composition shows high resolution, wide DOF, small LER and high sensitivity to form a good pattern shape in lithographic processes.Type: GrantFiled: October 14, 2011Date of Patent: March 31, 2015Assignee: Central Glass Company, LimitedInventors: Ryozo Takihana, Satoru Narizuka
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Patent number: 8993210Abstract: A salt represented by the formula (I): wherein R1 and R2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group which can have one or more fluorine atoms and in which one or more —CH2— can be replaced by —O— or —CO—, R3 represents a group having a cyclic ether structure, and Z1+ represents an organic cation.Type: GrantFiled: February 15, 2011Date of Patent: March 31, 2015Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Hiromu Sakamoto
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Patent number: 8956803Abstract: The present invention provides a sulfonium salt used in a resist composition that can give a pattern having a high resolution, especially an excellent rectangularity of a pattern form and a small roughness, while not readily generating a defect, in the photolithography using a high energy beam as a light source; a resist composition that contains the sulfonium salt; and a patterning process using this resist composition, wherein the sulfonium salt is shown by the following general formula (1a), wherein each of R and R0 independently represents a hydrogen atom, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 30 carbon atoms which may be optionally substituted by a heteroatom or interposed by a heteroatom.Type: GrantFiled: December 6, 2013Date of Patent: February 17, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Tomohiro Kobayashi, Akihiro Seki, Masayoshi Sagehashi, Masahiro Fukushima
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Patent number: 8932797Abstract: A photoacid generator compound has formula (I): G+Z???(I) wherein G has formula (II): In formula (II), X is S or I, each R0 is commonly attached to X and is independently C1-30 alkyl; polycyclic or monocyclic C3-30 cycloalkyl; polycyclic or monocyclic C6-30 aryl; or a combination comprising at least one of the foregoing groups. G has a molecular weight greater than 263.4 g/mol, or less than 263.4 g/mol. One or more R0 groups are further attached to an adjacent R0 group, a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 2 or 3. Z in formula (I) comprises the anion of a sulfonic acid, a sulfonimide, or a sulfonamide. A photoresist and coated film also includes the photoacid generator, and a method of forming an electronic device uses the photoresist.Type: GrantFiled: November 30, 2011Date of Patent: January 13, 2015Assignees: Dow Global Technologies LLC, Rohm and Haas Electronic Materials LLCInventors: James W. Thackeray, Suzanne M. Coley, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour, Owendi Ongayi, Vipul Jain
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Patent number: 8921029Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, R2, RII1, RII2, LII1, YII1, RII3, RII4, RII5, RII6, RII7, n, s and RII8 are defined in the specification.Type: GrantFiled: July 18, 2012Date of Patent: December 30, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
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Patent number: 8921028Abstract: A salt represented by the formula (I) and a resist composition containing the salt are provided, wherein Q1, Q2, L1, ring W1, Re1, Re2, Re3, Re4, Re5, Re6, Re7, Re8, Re9, Re10, Re11, Re12, Re13 and Z are defined in the specification.Type: GrantFiled: March 7, 2012Date of Patent: December 30, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Koji Ichikawa
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Patent number: 8906591Abstract: 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: December 9, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8900792Abstract: A compound has formula (I): Q-O-(A)-Z?G+??(I) wherein Q is a halogenated or non-halogenated, C2-30 olefin-containing group, A is a fluorine-substituted C1-30 alkylene group, a fluorine-substituted C3-30 cycloalkylene group, a fluorine-substituted C6-30 arylene group, or a fluorine-substituted C7-30 alkylene-arylene group, Z is an anionic group comprising sulfonate, sulfonamide, or sulfonimide, and G+ has formula (II): wherein X is S or I, each R0 is halogenated or non-halogenated and is independently C1-30 alkyl group; a polycyclic or monocyclic C3-30 cycloalkyl group; a polycyclic or monocyclic C4-30 aryl group; or a combination of these, wherein when X is S, one of the R0 groups is optionally attached to one adjacent R0 group by a single bond, and a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 3. A copolymer, a photoresist, a coated substrate and method of patterning are disclosed.Type: GrantFiled: December 29, 2011Date of Patent: December 2, 2014Assignees: Rohm and Haas Electronic Materials LLC, Dow Global Technologies LLCInventors: James W. Thackeray, Suzanne M. Coley, Vipul Jain, Owendi Ongayi, James F. Cameron, Paul J. Labeaume, Ahmad E. Madkour
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Patent number: 8900794Abstract: A photoacid generator compound has the formula (I): [A-(CHR1)p]k-(L)-(CH2)m—(C(R2)2)n—SO3?Z+??(I) wherein A is a substituted or unsubstituted, monocyclic, polycyclic, or fused polycyclic C5 or greater cycloaliphatic group optionally comprising O, S, N, F, or a combination comprising at least one of the foregoing, R1 is H, a single bond, or a substituted or unsubstituted C1-30 alkyl group, wherein when R1 is a single bond, R1 is covalently bonded to a carbon atom of A, each R2 is independently H, F, or C1-4 fluoroalkyl, wherein at least one R2 is not hydrogen, L is a linking group comprising a sulfonate group, a sulfonamide group, or a C1-30 sulfonate or sulfonamide-containing group, Z is an organic or inorganic cation, p is an integer of 0 to 10,k is 1 or 2, m is an integer of 0 or greater, and n is an integer of 1 or greater.Type: GrantFiled: September 28, 2012Date of Patent: December 2, 2014Assignee: Rohm and Haas Electronic Materials LLCInventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, Shintaro Yamada, William Williams, III
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Patent number: 8889333Abstract: A salt represented by formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, L2 and L3 respectively represent a single bond or a C1-C6 divalent saturated alkyl group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, ring W1 and ring W2 respectively represent a C3-C36 hydrocarbon ring, R1 and R2 respectively represent a hydrogen atom or C1-C6 alkyl group, R3 represents C1-C6 alkyl group, t represents an integer of 0 to 2 and Z+ represents an organic counter ion.Type: GrantFiled: April 10, 2012Date of Patent: November 18, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Isao Yoshida, Yuko Yamashita
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Patent number: 8871423Abstract: A photoresist composition for fabricating a probe array is provided. The photoresist composition includes a photoacid generator having an onium salt and an i-line reactive sensitizer.Type: GrantFiled: January 28, 2011Date of Patent: October 28, 2014Assignee: Samsung Electronics Co., Ltd.Inventors: Hyo-Jin Yun, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim, Jin-A Ryu, Myung-Sun Kim, Se-Kyung Baek, Soo-Kyung Kim, Ji-Yun Ham
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Patent number: 8871429Abstract: 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: October 28, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8852846Abstract: 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-C20 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, W represents a group represented by the formula (W1), (W2), (W3), (W4) or (W5): and Z+ represents an organic counter ion.Type: GrantFiled: April 4, 2012Date of Patent: October 7, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Yukako Anryu, Koji Ichikawa
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Patent number: 8852845Abstract: Provided is a actinic ray-sensitive or radiation-sensitive resin composition including (P) a resin containing (A) a repeating unit having an ionic structure moiety that contains a cation represented by formula (Ia) and is capable of producing an acid anion on the side chain upon irradiation with an actinic ray or radiation: wherein each of R1a to R13a independently represents a hydrogen atom or a monovalent substituent and may combine together to form a ring, and Z represents a single bond or a divalent linking group.Type: GrantFiled: December 18, 2009Date of Patent: October 7, 2014Assignee: FUJIFILM CorporationInventors: Hidenori Takahashi, Tomotaka Tsuchimura, Toru Tsuchihashi, Katsuhiro Yamashita, Hideaki Tsubaki
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Patent number: 8846291Abstract: A resist composition including: a base component (A) which exhibits changed solubility in a developing solution under action of acid; a nitrogen-containing organic compound component (C) containing a compound (C1) represented by general formula (c1) shown below; and an acid generator component (B) which generates acid upon exposure, provided that the compound (C1) is excluded from the acid generator component (B): wherein RN represents a nitrogen-containing heterocyclic group which may have a substituent; X0 represents a linear or branched divalent aliphatic hydrocarbon group of 1 to 10 carbon atoms, a cyclic divalent aliphatic hydrocarbon group of 3 to 20 carbon atoms or a divalent aliphatic hydrocarbon group of 3 to 20 carbon having a cyclic partial structure, or any one of these groups in which some or all of the hydrogen atoms thereof have been substituted with fluorine atoms; and M+ represents an organic cation.Type: GrantFiled: December 6, 2011Date of Patent: September 30, 2014Assignee: Tokyo Ohka Kogyo Co. Ltd.Inventors: Yoshiyuki Utsumi, Kenichiro Miyashita, Akiya Kawaue
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Patent number: 8846293Abstract: The actinic ray-sensitive or radiation-sensitive resin composition of the present invention contains (A) a resin capable of increasing the solubility in an alkaline developer by the action of an acid, and (C) at least one selected from the group of compounds represented by the following formula (ZI-3), (ZI-4) or (ZI-5) and capable of generating an acid upon irradiation of actinic rays or radiation, wherein the resin (A) contains at least one repeating unit having a group capable of decomposing by the action of an acid to leave a leaving group having a ring structure, and the leaving group having a ring structure has at least one of a polar group as a substituent and a polar atom as a part of the ring structure, and a compound derived from the leaving group having a ring structure has a logP value of not less than 0 and less than 2.8.Type: GrantFiled: March 27, 2012Date of Patent: September 30, 2014Assignee: FUJIFILM CorporationInventors: Yusuke Iizuka, Akinori Shibuya, Naohiro Tango, Shohei Kataoka
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Patent number: 8835097Abstract: There is disclosed a sulfonium salt shown by the following general formula (1). There can be a sulfonium salt capable of introducing an acid-generating unit generating an acid having an appropriate acid strength and not impairing adhesion with a substrate into a base polymer; a polymer using the said sulfonium salt; a chemically amplified resist composition using the said polymer as a base polymer; and a patterning process using the said chemically amplified resist composition.Type: GrantFiled: May 21, 2012Date of Patent: September 16, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Daisuke Domon, Keiichi Masunaga, Satoshi Watanabe
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Patent number: 8835091Abstract: A micro-structure is manufactured by patterning a sacrificial film, forming an inorganic material film on the pattern, and etching away the sacrificial film pattern through an aperture to define a space having the contour of the pattern. The patterning stage includes the steps of (A) coating a substrate with a composition comprising a cresol novolac resin, a crosslinker, and a photoacid generator, (B) heating to form a sacrificial film, (C) patternwise exposure, (D) development to form a sacrificial film pattern, and (E) forming crosslinks within the cresol novolac resin.Type: GrantFiled: May 18, 2012Date of Patent: September 16, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yoshinori Hirano, Hideyoshi Yanagisawa
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Patent number: 8765352Abstract: A positive 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) containing a compound represented by general formula (b1-1) shown below (wherein Z+ represents an organic cation).Type: GrantFiled: September 1, 2011Date of Patent: July 1, 2014Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoshiyuki Utsumi, Takehiro Seshimo
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Patent number: 8735044Abstract: A salt represented by the formula (a): wherein Q1 and Q2 each independently represent a fluorine atom etc., X1 represents a single bond etc., X2 represents a single bond etc., Y1 represents a C3-C6 alicyclic hydrocarbon group etc., with the proviso that —X2—Y1 group has one or more fluorine atoms, and Z+ represents an organic counter cation, and a photoresist composition comprising the salt represented by the formula (a) 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: GrantFiled: May 25, 2010Date of Patent: May 27, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Isao Yoshida
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Patent number: 8685616Abstract: The present invention provides photoacid generators for use in chemically amplified resists and lithographic processes using the same.Type: GrantFiled: June 10, 2009Date of Patent: April 1, 2014Assignee: University Of North Carolina At CharlotteInventors: Kenneth E. Gonsalves, Mingxing Wang
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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: 8658345Abstract: 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 13, 2012Date of Patent: February 25, 2014Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8642253Abstract: To provide a resist composition for negative tone development, which can form a pattern having a good profile improved in the pattern undercut and moreover, can reduce the line edge roughness and enhance the in-plane uniformity of the pattern dimension, and a pattern forming method using the same. A resist composition for negative tone development, comprising (A) a resin capable of increasing the polarity by the action of an acid to increase the solubility in a positive tone developer and decrease the solubility in a negative tone developer, (B) a compound capable of generating an acid having an acid dissociation index pKa of ?4.0 or less upon irradiation with an actinic ray or radiation, and (C) a solvent; and a pattern forming method using the same.Type: GrantFiled: November 8, 2010Date of Patent: February 4, 2014Assignee: FUJIFILM IncorporatedInventor: Hideaki Tsubaki
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Patent number: 8632939Abstract: A polymer comprising recurring units having a fluorinated carboxylic acid onium salt structure on a side chain is used to formulate a chemically amplified positive resist composition. When the composition is processed by lithography to form a positive pattern, the diffusion of acid in the resist film is uniform and slow, and the pattern is improved in LER.Type: GrantFiled: February 25, 2011Date of Patent: January 21, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Keiichi Masunaga, Satoshi Watanabe, Jun Hatakeyama, Youichi Ohsawa, Daisuke Domon
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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: 8614046Abstract: A salt represented by the formula (I-Pa): wherein Xpa represents a single bond or a C1-C4 alkylene group, Rpa represents a single bond, a C4-C36 divalent alicyclic hydrocarbon group or a C6-C36 divalent aromatic hydrocarbon group, and one or more methylene groups in the divalent alicyclic hydrocarbon group can be replaced by —O— or —CO—, Ypa represents a polymerizable group, and Zpa+ represents an organic cation.Type: GrantFiled: July 9, 2010Date of Patent: December 24, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Masako Sugihara, Yuko Yamashita
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Patent number: 8609317Abstract: A salt represented by the formula (I—Pb): wherein Xpb represents a single bond or —O—, Rpb represents a single bond etc., Ypb represents a polymerizable group, Zpb represents an organic group, Xpc represents a single bond or a C1-C4 alkylene group, and Rpc represents a C1-C10 aliphatic hydrocarbon group which can have one or more substituents etc.Type: GrantFiled: July 9, 2010Date of Patent: December 17, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Masako Sugihara, Yuko Yamashita
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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: 8592132Abstract: A resist composition includes (A1) a resin having a structural unit represented by the formula (I), (A2) a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and (B) an acid generator having an acid-labile group. wherein R1 represents a hydrogen atom or a methyl group; A1 represents a C1 to C6 alkanediyl group; R2 represents a C1 to C10 hydrocarbon group having a fluorine atom.Type: GrantFiled: February 24, 2012Date of Patent: November 26, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Satoshi Yamaguchi, Yuki Suzuki
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Patent number: 8574812Abstract: A resist composition of the invention includes: (A1) a resin having a structural unit represented by the formula (I), (A2) a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and (B) an acid generator represented by the formula (II), wherein R1, A1, R2, Q1, Q2, L1, ring W1, and Z+ are defined in the specification.Type: GrantFiled: February 24, 2012Date of Patent: November 5, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Satoshi Yamaguchi
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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: 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: 8518630Abstract: 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 13, 2012Date of Patent: August 27, 2013Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8512934Abstract: Compounds of the formula (I), wherein X is a single bond, CRaRb O, S, NRC, NCORC, CO, SO or SO2; L, L1, L2, L3, L4, L5, L6, L7 and L8 are for example hydrogen, R1 or COT; T denotes T1 or O-T2; T1 and T2 for example are hydrogen, C1-C20alkyl, C3-C12cycloalkyl, C2-C20alkenyl, C5-C12cycloalkenyl, C6-C14aryl, C3-C12heteroaryl, C1-C20alkyl substituted by one or more D, C2-C20alkyl interrupted by one or more E, C2-C20alkyl substituted by one or more D and interrupted by one or more E or Q; R1, R2, R3, R4, Ra, Rb and Rc are T1; D is for example R5, OR5, SR5 or Q1; E is for example O, S, COO or Q2; R5 and R6 for example are hydrogen, C1-C12alkyl or phenyl; Q is for example C6-C12bicycloalkyl, C6-C12bicycloalkenyl or C6-C12tricycloalkyl; Q1 is for example, C6-C14aryl or C3-C12heteroaryl; Q2 is for example C6-C14arylene or C3-C12heteroarylene; Y is an anion; and M is a cation; provided that at least one of L, L1, L2, L3, L4, L5, L6, L7 and L8 is other than hydrogen; and provided that (i) at least one of T1 or T2 is a gType: GrantFiled: September 29, 2008Date of Patent: August 20, 2013Assignee: BASF SEInventors: Pascal Hayoz, Hitoshi Yamato
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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: 8426103Abstract: A positive resist composition for use with electron beam, X-ray or EUV and a pattern forming method using the positive resist composition are provided, the positive resist composition including: (A) a resin capable of decomposing under an action of an acid to increase a dissolution rate in an aqueous alkali solution; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (C) a basic compound; and (D) an organic solvent, wherein the entire solid content concentration in the resist composition is from 1.0 to 4.5 mass % and a ratio of (B) the compound capable of generating an acid upon irradiation with actinic rays or radiation is from 10 to 50 mass % based on the entire solid content.Type: GrantFiled: February 12, 2009Date of Patent: April 23, 2013Assignee: FUJIFILM CorporationInventor: Katsuhiro Yamashita
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Patent number: 8367297Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) including an acid generator (B1) containing a compound having a cation moiety represented by general formula (I) (in the formula, R5 represents a hydrogen atom or an organic group of 1 to 30 carbon atoms which may have a substituent; and Q5 represents a single bond or a divalent linking group).Type: GrantFiled: December 9, 2009Date of Patent: February 5, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Shinichi Hidesaka, Natsuko Maruyama
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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: 8343706Abstract: 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: January 25, 2010Date of Patent: January 1, 2013Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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Patent number: 8318404Abstract: A salt represented by the formula (a1): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C4 perfluoroalkyl group, X1 represents —CO—O—Xa1— or —CH2—O—Xa2— wherein Xa1 and Xa2 independently each represent a C1-C15 alkylene group and one or more —CH2— in the alkylene group can be replaced by —O— or —CO—, Y1 represents a C3-C36 alicyclic hydrocarbon group or a C6-C24 aromatic hydrocarbon group, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O— or —CO—, and Z+ represents an organic cation.Type: GrantFiled: June 9, 2010Date of Patent: November 27, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Masako Sugihara, Hiromu Sakamoto
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Patent number: 8298748Abstract: A positive resist composition including a base component (A?) which exhibits increased solubility in an alkali developing solution under action of acid and generates acid upon exposure, the base component (A?) including a polymeric compound (A1?) having a structural unit (a5-1) represented by general formula (a5-1), a structural unit (a0-1) represented by general formula (a0-1) and a structural unit (a0-2) that generates acid upon exposure, the structural unit (a0-2) containing a group represented by general formula (a0-2?) (wherein X? represents an anion moiety represented by one of general formulas (1) to (5)).Type: GrantFiled: May 17, 2010Date of Patent: October 30, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Yoshitaka Komuro, Takeyoshi Mimura, Daichi Takaki
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Patent number: 8288077Abstract: The object of the present invention is to provide a chemically amplified resist composition excellent in a resolution and a mask error enhancement factor. By employing the salt represented by the formulae (A1) as an acid generator of a resist composition, the above mentioned object is achieved. wherein Z+ represents an organic cation, Q1 and Q2 each independently represent a fluorine atom or a perfluoroalkyl group, Ra2 represents a divalent alicyclic hydrocarbon group pr the like, Ra2 represents an elimination group represented by the formulae (II-1) or (II-2). In the formulae (II-1) or (II-2), Ra3 and Ra4 each independently represent a hydrogen atom or an aliphatic hydrocarbon group, Ra5 represents an aliphatic hydrocarbon group, Ra6 represents a divalent aliphatic hydrocarbon group, and Ra7 represents an aliphatic hydrocarbon group.Type: GrantFiled: July 27, 2010Date of Patent: October 16, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Isao Yoshida, Satoshi Yamaguchi
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Patent number: 8288076Abstract: A chemically amplified resist composition comprises a polymer comprising units having polarity to impart adhesion and acid labile units adapted to turn alkali soluble under the action of acid. The polymer comprises recurring units having formula (1) wherein R1 is H, F, CH3 or CF3, Rf is H, F, CF3 or CF2CF3, A is a divalent hydrocarbon group, R2, R3 and R4 are alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl. Recurring units containing an aromatic ring structure are present in an amount ?60 mol % and the recurring units having formula (1) are present in an amount <5 mol %.Type: GrantFiled: May 28, 2010Date of Patent: October 16, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Keiichi Masunaga, Satoshi Watanabe, Akinobu Tanaka, Daisuke Domon
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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