Sulfur Compound Containing Patents (Class 430/921)

Cross-Reference Art Collections

Sulfur in heterocyclic ring (Class 430/922)
  • Patent number: 9488914
    Abstract: Disclosed is a fluorine-containing sulfonic acid salt resin having a repeating unit represented by the following general formula (3). In the formula, each A independently represents a hydrogen atom, a fluorine atom or a trifluoromethyl group, and n represents an integer of 1-10. W represents a bivalent linking group, R01 represents a hydrogen atom or a monovalent organic group, and M+ represents a monovalent cation. A resist composition containing this resin is further superior in sensitivity, resolution and reproducibility of mask pattern and is capable of forming a pattern with a low LER.
    Type: Grant
    Filed: January 17, 2013
    Date of Patent: November 8, 2016
    Assignee: Central Glass Company, Limited
    Inventors: Kazunori Mori, Satoru Narizuka, Yuji Hagiwara, Fumihiro Amemiya, Masaki Fujiwara
  • Patent number: 9040220
    Abstract: A resist composition including a base component which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component which generates acid upon exposure, the acid-generator including an acid generator consisting of a compound represented by general formula (b1-1) shown below: In which RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Grant
    Filed: March 2, 2012
    Date of Patent: May 26, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9034556
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) including an acid generator (B1) consisting of a compound represented by general formula (b1-1) shown below: wherein RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Grant
    Filed: December 18, 2008
    Date of Patent: May 19, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9029070
    Abstract: 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: Grant
    Filed: November 2, 2012
    Date of Patent: May 12, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito
  • Patent number: 9012129
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) including a compound represented by (b1-1), a compound represented by (b1-1?) and/or a compound represented by (b1-1?) (R1?-R3? represents an aryl group or an alkyl group, provided that at least one of R1?-R3? represents a substituted aryl group being substituted with a group represented by (b1-1-0), and two of R1?-R3? may be mutually bonded to form a ring with the sulfur atom; X represents a C3-C30 hydrocarbon group; Q1 represents a carbonyl group-containing divalent linking group; X10 represents a C1-C30 hydrocarbon group; Q3 represents a single bond or a divalent linking group; Y10 represents —C(?O)— or —SO2—; Y11 represents a C1-C10 alkyl group or a fluorinated alkyl group: Q2 represents a single bond or an alkylene group; and W represents a C2-C10 alkylene group).
    Type: Grant
    Filed: January 6, 2014
    Date of Patent: April 21, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
  • Patent number: 9005874
    Abstract: There are provided a novel compound, a polymeric compound, a resist composition, an acid generator and a method of forming a resist pattern the compound represented by general formula (1-1): wherein each of R1 and R3 independently represents a single bond or a divalent linking group; A represents a divalent linking group; each of R2 and R4 independently represents a hydroxyl group, a hydrocarbon group which may have a substituent, or a group represented by general formula (1-an1), (1-an2) or (1-an3), provided that at least one of R2 and R4 represents a group represented by general formula (1-an1), (1-an2) or (1-an3); and n0 is preferably 0 or 1, and wherein Y1 represents a single bond or —SO2—; R5 represents a linear or branched monovalent hydrocarbon group of 1 to 10 carbon atoms, cyclic monovalent hydrocarbon group of 3 to 20 carbon atoms or monovalent hydrocarbon group of 3 to 20 carbon atoms having a cyclic partial structure which may be substituted with a fluorine atom; and M+ represents an organic ca
    Type: Grant
    Filed: April 18, 2012
    Date of Patent: April 14, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshitaka Komuro, Yoshiyuki Utsumi, Akiya Kawaue, Masatoshi Arai
  • Patent number: 9005871
    Abstract: 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: Grant
    Filed: October 8, 2009
    Date of Patent: April 14, 2015
    Assignee: BASF SE
    Inventors: Hitoshi Yamato, Toshikage Asakura, Yuichi Nishimae
  • Patent number: 9005872
    Abstract: 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: Grant
    Filed: February 16, 2012
    Date of Patent: April 14, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Sho Abe, Hideto Nito
  • Patent number: 8993210
    Abstract: 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: Grant
    Filed: February 15, 2011
    Date of Patent: March 31, 2015
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto
  • Patent number: 8993212
    Abstract: A resist composition according to the present invention includes at least a base resin, a photoacid generator and a solvent, wherein the photoacid generator comprises a fluorine-containing sulfonic acid salt of the following general formula (4). In the formula, X independently represents a hydrogen atom or a fluorine atom; n represents an integer of 1 to 6; R1 represents a hydrogen atom, or an alkyl, alkenyl, oxoalkyl, aryl or aralkyl group; any of hydrogen atoms on carbons in R1 may be substituted with a substituent; R2 represents RAO or RBRCN; and A represents a divalent group. This fluorine-containing sulfonic acid salt can serve as a photoacid generator having high solubility in a resist solvent and thus can suitably be used for a resist composition such that the resist composition shows high resolution, wide DOF, small LER and high sensitivity to form a good pattern shape in lithographic processes.
    Type: Grant
    Filed: October 14, 2011
    Date of Patent: March 31, 2015
    Assignee: Central Glass Company, Limited
    Inventors: Ryozo Takihana, Satoru Narizuka
  • Patent number: 8980527
    Abstract: A resist composition is provided comprising a polymer comprising recurring units having a carboxyl group substituted with an acid labile group, an acid generator, a sulfonium or iodonium salt of fluoroalkanesulfonamide and an organic solvent. A positive pattern is formed by applying the resist composition onto a substrate, prebaking to form a resist film, exposing the resist film to high-energy radiation, baking, and immersing in an alkaline developer to dissolve away the exposed region of resist film, but not the unexposed region.
    Type: Grant
    Filed: January 4, 2013
    Date of Patent: March 17, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Jun Hatakeyama
  • Patent number: 8980524
    Abstract: A positive resist composition including a base component (A) which exhibits increased solubility in an alkali developing solution under action of acid, an acid-generator component (B) which generates acid upon exposure and a fluorine-containing polymeric compound (C?) which generates acid upon exposure, the base component (A) having a structural unit (a0-1) represented by general formula (a0-1) and a structural unit (a1) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group, and the fluorine-containing polymeric compound (C?) having a structural unit (c0) which generates acid upon exposure and a structural unit (c1) represented by formula (c1) (wherein R2 represents a divalent linking group, R3 represents a cyclic group containing —SO2— within the ring skeleton, Q0 represents a single bond or a divalent linking group, and R0 represents an organic group which may have a fluorine atom).
    Type: Grant
    Filed: December 27, 2010
    Date of Patent: March 17, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tomoyuki Hirano, Daiju Shiono, Masatoshi Arai
  • Patent number: 8975002
    Abstract: A positive resist composition for immersion exposure includes the following (A) to (D): (A) a resin capable of decomposing by an action of an acid to increase a solubility of the resin in an alkali developer; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (C) a resin having at least either one of a fluorine atom and a silicon atom; and (D) a mixed solvent containing at least one kind of a solvent selected from the group consisting of solvents represented by any one of the following formulae (S1) to (S3) as defined in the specification, in which a total amount of the at least one kind of the solvent is from 3 to 20 mass % based on all solvents of the mixed solvent (D).
    Type: Grant
    Filed: August 15, 2013
    Date of Patent: March 10, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Kei Yamamoto, Hiroshi Saegusa
  • Patent number: 8968980
    Abstract: A radiation-sensitive resin composition includes an acid-dissociable group-containing resin, and a compound shown by the following general formula (1). wherein Z? represents a monovalent anion shown by a general formula (2), M+ represents a monovalent onium cation, R1 represents a linear or branched alkyl group having 1 to 12 carbon atoms substituted or unsubstantiated with a fluorine atom, or a linear or branched alkoxy group having 1 to 12 carbon atoms, and n is 1 or 2.
    Type: Grant
    Filed: November 4, 2011
    Date of Patent: March 3, 2015
    Assignee: JSR Corporation
    Inventors: Ken Maruyama, Kota Nishino, Kazuki Kasahara, Hirokazu Sakakibara
  • Patent number: 8962233
    Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes an arylsulfonium salt that when exposed to actinic rays or radiation, generates an acid, the arylsulfonium salt containing at least one aryl ring on which there are a total of one or more electron donating groups, the acid generated upon exposure to actinic rays or radiation having a volume of 240 ?3 or greater.
    Type: Grant
    Filed: January 28, 2011
    Date of Patent: February 24, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Takeshi Kawabata, Tomotaka Tsuchimura, Takayuki Ito
  • Patent number: 8956806
    Abstract: A method and material layer for forming a pattern are disclosed. The method includes providing a substrate; forming a first material layer over the substrate; forming a second material layer over the first material layer, wherein the second material layer comprises a photoacid generator and a photobase generator; and exposing one or more portions of the second material layer.
    Type: Grant
    Filed: September 18, 2009
    Date of Patent: February 17, 2015
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Chien-Wei Wang, Ching-Yu Chang, Burn Jeng Lin
  • Patent number: 8956799
    Abstract: A photoacid generator includes those of formula (I): wherein each Ra in formula 1 is independently H, F, a C1-10 nonfluorinated organic group, C1-10 fluorinated organic group, or a combination comprising at least one of the foregoing, provided at least one Ra is F or a C1-10 fluorinated organic group, the C1-10 fluorinated and nonfluorinated organic groups each optionally comprising O, S, N, or a combination comprising at least one of the foregoing heteroatoms; L1 is a linking group comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing; G+ is an onium salt of the formula (II): wherein in formula (II), X is S or I, each R0 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 comprising at least one of the foregoing, provided at least one R0 is substituted where each R0 is a C6 monocyclic aryl group, and wherein when X is I, a is 2, and where X is S, a is 3,
    Type: Grant
    Filed: December 12, 2012
    Date of Patent: February 17, 2015
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, William Williams, III
  • Patent number: 8940473
    Abstract: A resist composition contains (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 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; R3 and R4 independently represent a fluorine atom or a C1 to C6 perfluoroalkyl group; X1 represents an C1 to C17 divalent saturated hydrocarbon group; R5 represents a group having cyclic ether structure; and Z1+ represents an organic cation.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: January 27, 2015
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yuichi Mukai, Satoshi Yamamoto
  • Patent number: 8940471
    Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes a compound that when exposed to actinic rays or radiation, generates any of acids of general formula (I) below, in which W1 represents an optionally substituted alkylene group, W2 represents a bivalent connecting group, W3 represents an optionally substituted organic group having 15 or more carbon atoms, and Z represents a hydroxyl group or a fluoroalkylsulfonamido group having at least one fluorine atom introduced therein as a substituent.
    Type: Grant
    Filed: September 30, 2010
    Date of Patent: January 27, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Takeshi Kawabata, Tomotaka Tsuchimura, Takayuki Ito
  • Patent number: 8932797
    Abstract: A photoacid generator compound has formula (I): G+Z???(I) wherein G has formula (II): In formula (II), X is S or I, each R0 is commonly attached to X and is independently C1-30 alkyl; polycyclic or monocyclic C3-30 cycloalkyl; polycyclic or monocyclic C6-30 aryl; or a combination comprising at least one of the foregoing groups. G has a molecular weight greater than 263.4 g/mol, or less than 263.4 g/mol. One or more R0 groups are further attached to an adjacent R0 group, a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 2 or 3. Z in formula (I) comprises the anion of a sulfonic acid, a sulfonimide, or a sulfonamide. A photoresist and coated film also includes the photoacid generator, and a method of forming an electronic device uses the photoresist.
    Type: Grant
    Filed: November 30, 2011
    Date of Patent: January 13, 2015
    Assignees: Dow Global Technologies LLC, Rohm and Haas Electronic Materials LLC
    Inventors: James W. Thackeray, Suzanne M. Coley, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour, Owendi Ongayi, Vipul Jain
  • Patent number: 8921027
    Abstract: A radiation-sensitive resin composition includes an acid-labile group-containing resin, and a compound shown by the following general formula (i). R1 represents a hydrogen atom or the like, R2 represents a single bond or the like, R3 represents a linear or branched unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms or the like, and X+ represents an onium cation.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: December 30, 2014
    Assignee: JSR Corporation
    Inventors: Ryuichi Serizawa, Nobuji Matsumura, Hirokazu Sakakibara
  • Patent number: 8921029
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, R2, RII1, RII2, LII1, YII1, RII3, RII4, RII5, RII6, RII7, n, s and RII8 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: December 30, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
  • Patent number: 8916333
    Abstract: A radiation-sensitive resin composition includes a polymer and a photoacid generator. The polymer includes a first structural unit shown by a formula (a1), a second structural unit shown by a formula (a2), and a third structural unit having a lactone structure. A content of the first structural unit in the polymer being 50 mol % or more based on total structural units included in the polymer. The first structural unit is preferably a structural unit shown by a formula (a1-1).
    Type: Grant
    Filed: September 28, 2012
    Date of Patent: December 23, 2014
    Assignee: JSR Corporation
    Inventors: Hiroshi Tomioka, Noboru Otsuka, Akimasa Soyano
  • Patent number: 8906589
    Abstract: The present invention provides 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 in which one or more —CH2— can be replaced by —O— or —CO— and which can have one or more fluorine atoms, R3 represents a hydrogen atom or a methyl group, and Z1+ represents an organic counter cation, and a photoresist composition containing the same.
    Type: Grant
    Filed: February 15, 2011
    Date of Patent: December 9, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto
  • Patent number: 8906591
    Abstract: 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: Grant
    Filed: September 14, 2012
    Date of Patent: December 9, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8900794
    Abstract: 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: Grant
    Filed: September 28, 2012
    Date of Patent: December 2, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, Shintaro Yamada, William Williams, III
  • Patent number: 8900796
    Abstract: The present invention provides an acid generator generates a sulfonic acid represented by the following general formula (1) in response to high-energy beam or heat: To provide a novel acid generator which is suitably used as an acid generator for a resist composition, which solves the problems of LER and a depth of focus and can be effectively and widely used particularly without degradation of a resolution, a chemically amplified resist composition using the same, and a patterning process.
    Type: Grant
    Filed: February 15, 2013
    Date of Patent: December 2, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Tomohiro Kobayashi, Masayoshi Sagehashi
  • Patent number: 8900791
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes any of the compounds of general formula (I) below; wherein: Ar represents an aromatic ring that may have a substituent other than the -(A-B) groups; n is an integer of 1 or greater; A represents any one, or a combination of two or more members selected from a single bond, an alkylene group, —O—, —S—, —C(?O)—, —S(?O)—, —S(?O)2— and —OS(?O)2—, provided that —C(?O)O— is excluded; B represents a group containing a hydrocarbon group having 4 or more carbon atoms wherein either a tertiary or a quaternary carbon atom is contained, when n is 2 or greater, the two or more -(A-B) groups may be identical to or different from each other; and M+ represents an organic onium ion.
    Type: Grant
    Filed: March 24, 2011
    Date of Patent: December 2, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Tomotaka Tsuchimura, Koji Shirakawa, Toru Tsuchihashi, Hideaki Tsubaki
  • Patent number: 8900792
    Abstract: 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: Grant
    Filed: December 29, 2011
    Date of Patent: December 2, 2014
    Assignees: Rohm and Haas Electronic Materials LLC, Dow Global Technologies LLC
    Inventors: James W. Thackeray, Suzanne M. Coley, Vipul Jain, Owendi Ongayi, James F. Cameron, Paul J. Labeaume, Ahmad E. Madkour
  • Patent number: 8895222
    Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition including (P) a resin which contains (A) a repeating unit having an ionic structure moiety capable of producing an acid anion on the side chain upon irradiation with an actinic ray or radiation, wherein a cation moiety of the ionic structure moiety has an acid-decomposable group or an alkali-decomposable group.
    Type: Grant
    Filed: March 23, 2010
    Date of Patent: November 25, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Tomotaka Tsuchimura, Hidenori Takahashi, Takayuki Ito, Takeshi Inasaki, Shohei Kataoka
  • Patent number: 8889336
    Abstract: A radiation-sensitive resin composition includes a compound represented by a formula (1), and a base polymer. A represents —CO— or —CH2—. R1 represents a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group having 3 to 30 ring atoms, or a combination of a first group and a second group. The first group is —CO—, —COO—, —OCO—, —O—CO—O—, —NHCO—, —CONH—, —NH—CO—O—, —O—CO—NH—, —NH—, —S—, —SO—, —SO2—, —SO2—O— or a combination thereof, and the second group is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group having 3 to 30 ring atoms or a combination thereof. A part or all of hydrogen atoms included in the hydrocarbon group and the heterocyclic group are not substituted or substituted. M+ represents a monovalent cation.
    Type: Grant
    Filed: May 30, 2013
    Date of Patent: November 18, 2014
    Assignee: JSR Corporation
    Inventor: Ken Maruyama
  • Patent number: 8889333
    Abstract: A salt represented by formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, L2 and L3 respectively represent a single bond or a C1-C6 divalent saturated alkyl group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, ring W1 and ring W2 respectively represent a C3-C36 hydrocarbon ring, R1 and R2 respectively represent a hydrogen atom or C1-C6 alkyl group, R3 represents C1-C6 alkyl group, t represents an integer of 0 to 2 and Z+ represents an organic counter ion.
    Type: Grant
    Filed: April 10, 2012
    Date of Patent: November 18, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Isao Yoshida, Yuko Yamashita
  • Patent number: 8883395
    Abstract: 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: Grant
    Filed: September 14, 2012
    Date of Patent: November 11, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8877424
    Abstract: A polymer is prepared from an adamantane methacrylate monomer whose alcoholic hydroxyl group is protected with an alicyclic-containing tertiary alkyl group. A photoresist composition comprising the polymer displays a high sensitivity and a high dissolution contrast during both alkaline development and organic solvent development.
    Type: Grant
    Filed: February 8, 2013
    Date of Patent: November 4, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayoshi Sagehashi, Jun Hatakeyama, Koji Hasegawa, Kazuhiro Katayama
  • Patent number: 8871423
    Abstract: 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: Grant
    Filed: January 28, 2011
    Date of Patent: October 28, 2014
    Assignee: 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
  • Patent number: 8871429
    Abstract: 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: Grant
    Filed: September 14, 2012
    Date of Patent: October 28, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8865392
    Abstract: Disclosed is a photosensitive resin composition containing a cationic photopolymerization initiator (A) and an epoxy resin (B) having two or more epoxy groups in each molecule, which is characterized in that the cationic photopolymerization initiator (A) is a cationic photopolymerization initiator (A-1) that is represented by formula (1).
    Type: Grant
    Filed: July 13, 2011
    Date of Patent: October 21, 2014
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Misato Oonishi, Naoko Imaizumi, Ryo Sakai, Nao Honda, Tadayuki Kiyoyanagi
  • Patent number: 8852845
    Abstract: 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: Grant
    Filed: December 18, 2009
    Date of Patent: October 7, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hidenori Takahashi, Tomotaka Tsuchimura, Toru Tsuchihashi, Katsuhiro Yamashita, Hideaki Tsubaki
  • Patent number: 8846303
    Abstract: There is disclosed a resist top coat composition, used in a patterning process onto a photoresist film, wherein a resist top coat is formed by using the resist top coat composition onto a photoresist film formed on a wafer, and then, after exposure, removal of the resist top coat and development of the photoresist film are performed to effect the patterning on the photoresist film, wherein the resist top coat composition contains a truxene compound having phenol groups shown by the following general formula (1). As a result, there is provided a resist top coat composition not only having an effect from an environment to a resist film reduced and effectively shielding an OOB light, but also reducing film loss of a resist pattern and bridging between patterns and having an effect to enhance sensitivity of the resist; and a patterning process using this.
    Type: Grant
    Filed: September 25, 2012
    Date of Patent: September 30, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Daisuke Kori
  • Patent number: 8846301
    Abstract: An orthogonal process for photolithographic patterning organic structures is disclosed. The disclosed process utilizes fluorinated solvents or supercritical CO2 as the solvent so that the performance of the organic conductors and semiconductors would not be adversely affected by other aggressive solvent. One disclosed method may also utilize a fluorinated photoresist together with the HFE solvent, but other fluorinated solvents can be used. In one embodiment, the fluorinated photoresist is a resorcinarene, but various fluorinated polymer photoresists and fluorinated molecular glass photoresists can be used as well. For example, a copolymer perfluorodecyl methacrylate (FDMA) and 2-nitrobenzyl methacrylate (NBMA) is a suitable orthogonal fluorinated photoresist for use with fluorinated solvents and supercritical carbon dioxide in a photolithography process.
    Type: Grant
    Filed: May 21, 2009
    Date of Patent: September 30, 2014
    Assignee: Cornell University
    Inventors: Christopher K. Ober, George Malliaras, Jin-Kyun Lee, Alexander Zakhidov, Margarita Chatzichristidi, Priscilla Taylor
  • Patent number: 8846291
    Abstract: 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: Grant
    Filed: December 6, 2011
    Date of Patent: September 30, 2014
    Assignee: Tokyo Ohka Kogyo Co. Ltd.
    Inventors: Yoshiyuki Utsumi, Kenichiro Miyashita, Akiya Kawaue
  • Patent number: 8846293
    Abstract: The actinic ray-sensitive or radiation-sensitive resin composition of the present invention contains (A) a resin capable of increasing the solubility in an alkaline developer by the action of an acid, and (C) at least one selected from the group of compounds represented by the following formula (ZI-3), (ZI-4) or (ZI-5) and capable of generating an acid upon irradiation of actinic rays or radiation, wherein the resin (A) contains at least one repeating unit having a group capable of decomposing by the action of an acid to leave a leaving group having a ring structure, and the leaving group having a ring structure has at least one of a polar group as a substituent and a polar atom as a part of the ring structure, and a compound derived from the leaving group having a ring structure has a logP value of not less than 0 and less than 2.8.
    Type: Grant
    Filed: March 27, 2012
    Date of Patent: September 30, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Yusuke Iizuka, Akinori Shibuya, Naohiro Tango, Shohei Kataoka
  • Patent number: 8846296
    Abstract: A composition is provided. The composition includes a polymer and a photosensitive acid generator capable of generating a first amount of acid upon exposure to a first dose of radiation and a second amount of acid upon exposure to a second dose of radiation. The second amount of acid is greater than the first amount of acid. The second dose is greater than the first dose. The composition includes a photosensitive base generator capable of generating a first amount of base upon exposure to the first dose and a second amount of base upon exposure to the second dose, where the first amount of base is greater than the first amount of acid and the second amount of base is less than the second amount of acid. The photosensitive base generator may include benzoin carbamates, O-carbamoylhydroxylamines, O-carbamoyloximes, aromatic sulfonamides, ?-lactones, N-(2-Arylethenyl)amides, azides, amides, oximines, quaternary ammonium salts, or amineimides.
    Type: Grant
    Filed: May 2, 2012
    Date of Patent: September 30, 2014
    Assignee: International Business Machines Corporation
    Inventors: Kuang-Jung Chen, Wu-Song Huang, Ranee Wai-Ling Kwong, Sen Liu, Pushkara R. Varanasi
  • Patent number: 8835091
    Abstract: 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: Grant
    Filed: May 18, 2012
    Date of Patent: September 16, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yoshinori Hirano, Hideyoshi Yanagisawa
  • Patent number: 8835097
    Abstract: There is disclosed a sulfonium salt shown by the following general formula (1). There can be a sulfonium salt capable of introducing an acid-generating unit generating an acid having an appropriate acid strength and not impairing adhesion with a substrate into a base polymer; a polymer using the said sulfonium salt; a chemically amplified resist composition using the said polymer as a base polymer; and a patterning process using the said chemically amplified resist composition.
    Type: Grant
    Filed: May 21, 2012
    Date of Patent: September 16, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Daisuke Domon, Keiichi Masunaga, Satoshi Watanabe
  • Patent number: 8822136
    Abstract: A negative pattern is formed by coating a resist composition onto a substrate, the resist composition comprising a polymer comprising recurring units having an acid labile group-substituted hydroxyl group, an acid generator, an onium salt of perfluoroalkyl ether carboxylic acid, and an organic solvent, prebaking, exposing, baking, and developing in an organic solvent such that the unexposed region of film is dissolved away and the exposed region of film is not dissolved. In image formation via positive/negative reversal by organic solvent development, the resist film is characterized by a high dissolution contrast between the unexposed and exposed regions.
    Type: Grant
    Filed: October 26, 2012
    Date of Patent: September 2, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Kazuhiro Katayama, Youichi Ohsawa
  • Patent number: 8815492
    Abstract: A chemically amplified positive resist composition comprising (A) a triarylsulfonium salt of 2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propionic acid, (B) an acid generator, (C) a base resin, and (D) an organic solvent is suited for ArF immersion lithography. The sulfonium salt is highly hydrophobic and little leached out in immersion water. By virtue of controlled acid diffusion, a pattern profile with high resolution can be constructed.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: August 26, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Takeshi Sasami, Jun Hatakeyama
  • Patent number: 8808975
    Abstract: A positive resist composition for immersion exposure comprises: (A) a resin capable of increasing its solubility in an alkali developer by an action of an acid, and (B) a compound capable of generating an acid upon irradiation with actinic ray or radiation, wherein the acid satisfies conditions of V?230 and V/S?0.93 taking van der Waals volume of the acid as V (?3), and van der Waals surface area of the acid as S (?2).
    Type: Grant
    Filed: August 17, 2010
    Date of Patent: August 19, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Haruki Inabe, Hiromi Kanda, Kunihiko Kodama
  • Patent number: 8808959
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) including a compound represented by (b1-1), a compound represented by (b1-1?) and/or a compound represented by (b1-1?) (R1?-R3? represents an aryl group or an alkyl group, provided that at least one of R1?-R3? represents a substituted aryl group being substituted with a group represented by (b1-1-0), and two of R1?-R3? may be mutually bonded to form a ring with the sulfur atom; X represents a C3-C30 hydrocarbon group; Q1 represents a carbonyl group-containing divalent linking group; X10 represents a C1-C30 hydrocarbon group; Q3 represents a single bond or a divalent linking group; Y10 represents —C(?O)— or —SO2—; Y11 represents a C1-C10 alkyl group or a fluorinated alkyl group: Q2 represents a single bond or an alkylene group; and W represents a C2-C10 alkylene group).
    Type: Grant
    Filed: November 10, 2009
    Date of Patent: August 19, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
  • Patent number: 8808960
    Abstract: A compound represented by the formula (I): wherein R1 represents a hydrogen atom etc., R2 and R3 each independently represent a hydrogen atom etc., R4 represents a C1-C8 divalent hydrocarbon group, R5 represents a single bond etc., and R6 represents an unsubstituted or substituted C6-C20 aromatic hydrocarbon group, a polymer comprising a structural unit derived from the compound represented by the formula (I) and a chemically amplified positive resist composition comprising the polymer, at least one acid generator and at least one solvent.
    Type: Grant
    Filed: March 8, 2010
    Date of Patent: August 19, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Akita, Isao Yoshida, Kazuhiko Hashimoto