Halogen Compound Containing Patents (Class 430/925)
  • 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: 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: 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: 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: 8956803
    Abstract: 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: Grant
    Filed: December 6, 2013
    Date of Patent: February 17, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Tomohiro Kobayashi, Akihiro Seki, Masayoshi Sagehashi, Masahiro Fukushima
  • 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: 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: 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: 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: 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: 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: 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: 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: 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: 8889335
    Abstract: A radiation-sensitive resin composition includes a compound represented by a formula (1), and a polymer that serves as a base resin. R1 is a monovalent group that includes at least two groups of —CO—, —NH—, —S—, and —SO2—, the at least two groups being each identical or different. A is a divalent hydrocarbon group or a divalent fluorohydrocarbon group having 1 to 5 carbon atoms. R is a fluorine atom or a hydrogen atom. a is an integer from 1 to 4. In a case where a plurality of R are present, each of the plurality of R is either identical or different. M+ is a monovalent cation.
    Type: Grant
    Filed: March 8, 2013
    Date of Patent: November 18, 2014
    Assignee: JSR Corporation
    Inventor: Ken Maruyama
  • 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: 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: 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: 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: 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: 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: 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: 8795946
    Abstract: Polymerizable ester compounds having formula (1) are novel wherein R1 is H, F, methyl or trifluoromethyl, R2 is an acid labile group, Aa is a divalent hydrocarbon group which may be separated by —O— or —C(?O)—, and k1 is 0 or 1. They are useful as monomers to produce polymers which are transparent to radiation ?500 nm. Radiation-sensitive resist compositions comprising the polymers as base resin exhibit excellent developed properties.
    Type: Grant
    Filed: July 13, 2012
    Date of Patent: August 5, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Masayoshi Sagehashi, Yuuki Suka, Masashi Ilo
  • Patent number: 8795944
    Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition including: (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a resin which contains (c) a repeating unit having at least one polarity conversion group and has at least either a fluorine atom or a silicon atom.
    Type: Grant
    Filed: December 11, 2009
    Date of Patent: August 5, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hiroshi Saegusa, Kaoru Iwato, Shuji Hirano, Yusuke Iizuka
  • Patent number: 8795945
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition, and a resist film and a pattern forming method using the composition are provided, the composition including (A) a compound capable of decomposing by the action of an acid to increase the solubility of the resin (A) in an alkali developer; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (C) a basic compound; and (D) a specific compound containing at least two specific alicyclic hydrocarbon groups each substituted with a hydroxyl group.
    Type: Grant
    Filed: March 4, 2011
    Date of Patent: August 5, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Kana Fujii, Takamitsu Tomiga, Toru Fujimori
  • Patent number: 8795942
    Abstract: There is disclosed a resist composition that remarkably improves the resolution of photolithography using a high energy beam such as ArF excimer laser light as a light source, and exhibits excellent resistance to surface roughness and side lobe under use of a halftone phase shift mask; and a patterning process using the resist composition. The positive resist composition at least comprises (A) a resin component comprising a repeating unit represented by the following general formula (1); (B) a photoacid generator generating sulfonic acid represented by the following general formula (2) upon exposure to a high energy beam; and (C) an onium salt where a cation is sulfonium represented by the following general formula (3), or ammonium represented by the following general formula (4); and an anion is represented by any one of the following general formulae (5) to (7).
    Type: Grant
    Filed: December 11, 2007
    Date of Patent: August 5, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Kobayashi, Youichi Ohsawa, Ryosuke Taniguchi
  • Patent number: 8790860
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition capable of forming a hole pattern which has an ultrafine pore diameter (for example, 60 nm or less) and has an excellent cross-sectional shape with excellent local pattern dimensional uniformity; and a resist film, a pattern forming method, a method for preparing an electronic device, and an electronic device, each using the same, are provided.
    Type: Grant
    Filed: September 11, 2012
    Date of Patent: July 29, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Kosuke Koshijima, Hidenori Takahashi, Shuhei Yamaguchi, Kei Yamamoto
  • Patent number: 8791293
    Abstract: According to the present invention, there is provided a fluorine-containing sulfonate resin having a repeating unit of the following general formula (3). In order to prevent deficiency such as roughness after pattern formation or failure in pattern formation, the fluorine-containing sulfonate resin incorporates therein a photoacid generating function and serves as a resist resin in which “a moiety capable of changing its developer solubility by the action of an acid” and “a moiety having a photoacid generating function” are arranged with regularity.
    Type: Grant
    Filed: August 2, 2012
    Date of Patent: July 29, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Kazunori Mori, Satoru Narizuka, Fumihiro Amemiya, Masaki Fujiwara
  • Patent number: 8778595
    Abstract: A resist composition containing a base component (A) which generates acid upon exposure, and exhibits changed solubility in a developing solution under the action of acid, wherein the base component (A) contains a polymeric compound (A1) having a structural unit (a5) represented by general formula (a5-0) shown below and a structural unit (a6) that generates acid upon exposure. In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, R1 represents a sulfur atom or an oxygen atom, R2 represents a single bond or a divalent linking group, and Y represents a hydrocarbon group in which a carbon atom or a hydrogen atom may be substituted with a substituent.
    Type: Grant
    Filed: November 16, 2012
    Date of Patent: July 15, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daichi Takaki, Daiju Shiono, Yoshiyuki Utsumi, Jun Iwashita
  • Patent number: 8771916
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition, includes: (A) a resin capable of increasing the solubility of the resin (A) in an alkali developer by the action of an acid; and (C) a resin having at least either a fluorine atom or a silicon atom and containing (c) a repeating unit having at least two or more polarity conversion groups.
    Type: Grant
    Filed: December 11, 2009
    Date of Patent: July 8, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Shuji Hirano, Kaoru Iwato, Hiroshi Saegusa, Yusuke Iizuka
  • Patent number: 8765352
    Abstract: 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: Grant
    Filed: September 1, 2011
    Date of Patent: July 1, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Takehiro Seshimo
  • Patent number: 8753792
    Abstract: A positive photosensitive composition comprising: (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (B1) a resin of which solubility in an alkali developer increases under an action of an acid; and (B2) a resin that has at least one group selected from (a) an alkali-soluble group and (b) a group capable of decomposing under an action of an alkali to produce an alkali-soluble group, and the resin (B2) does not have a group capable of decomposing under an action of an acid; and a pattern forming method using the same.
    Type: Grant
    Filed: October 29, 2010
    Date of Patent: June 17, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Fumiyuki Nishiyama
  • Patent number: 8748076
    Abstract: There is disclosed a resist composition comprising at least: (A) a polymer containing one or more repeating units having a structure shown by the following general formula (1) and/or (2), an alkaline-solubility of the polymer being increased by an acid, (B) a photo acid generator generating, with responding to a high energy beam, a sulfonic acid shown by the following general formula (3), and (C) an onium sulfonate shown by the following general formula (4). There can be a resist composition showing not only excellent LWR and pattern profile but also extremely good performance in pattern-fall resistance, and to provide a patterning process using the same.
    Type: Grant
    Filed: January 6, 2012
    Date of Patent: June 10, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takayuki Nagasawa, Tomohiro Kobayashi, Ryosuke Taniguchi, Masaki Ohashi
  • Patent number: 8748074
    Abstract: Polymers and compositions for forming self-imageable films encompassing such polymers that encompass norbornene-type repeating unit having at least one phenolic functionality and maleic anhydride-type repeating unit, which can be formulated to be either positive tone imaging or negative tone imaging. The films formed thereby are useful as self-imageable layers in the manufacture of microelectronic, such as semiconductor, and optoelectronic devices.
    Type: Grant
    Filed: November 23, 2011
    Date of Patent: June 10, 2014
    Assignees: Promerus, LLC, Sumitomo Bakelite Co., Ltd.
    Inventors: Osamu Onishi, Haruo Ikeda, Larry F. Rhodes, Pramod Kandanarachchi
  • Patent number: 8741545
    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: June 3, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8741543
    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 having an acid labile group, wherein R1, A1, A13, A14, X12 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: June 3, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi, Yuki Suzuki
  • Patent number: 8735046
    Abstract: A polymer obtained from copolymerization of a recurring unit having a carboxyl group and/or phenolic hydroxyl group substituted with an acid labile group with a methacrylate having a phenolic hydroxyl-bearing pyridine is useful as a base resin in a positive resist composition. The resist composition comprising the polymer is improved in contrast of alkali dissolution rate before and after exposure, acid diffusion control, resolution, and profile and edge roughness of a pattern after exposure.
    Type: Grant
    Filed: November 21, 2011
    Date of Patent: May 27, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8735047
    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, A13, A14, X12, Q1, Q2, L1, ring W1 and Z+ are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: May 27, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi
  • Patent number: 8728710
    Abstract: Disclosed is a method of making polysiloxane and polysilsesquioxane based hardmask respond to radiations with positive tone and negative tone simultaneously. Unradiated films are insoluble in developers, showing positivity tone. Radiated films are insoluble in developers as well, showing negative tone. Only half-way radiated films are soluble in developers. The dual-tone photo-imageable hardmask produces splitted patterns. Compositions of dual-tone photo-imageable hardmask based on the chemistry of polysiloxane and polysilsesquioxanes are disclosed as well. Further disclosed are processes of using photo-imageable hardmasks to create precursor structures on semiconductor substrates with or without an intermediate layer.
    Type: Grant
    Filed: March 30, 2010
    Date of Patent: May 20, 2014
    Inventor: Sam Xunyun Sun
  • Patent number: 8709699
    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, A13, A14, X12, Q1, Q2, L1, ring W, Rf1 and Rf2, n and Z+ are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: April 29, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takashi Hiraoka, Mitsuyoshi Ochiai
  • Patent number: 8709700
    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 13, 2012
    Date of Patent: April 29, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8703383
    Abstract: A copolymer has formula: wherein R1-R5 are independently H, C1-6 alkyl, or C4-6 aryl, R6 is a fluorinated or non-fluorinated C5-30 acid decomposable group; each Ar is a monocyclic, polycyclic, or fused polycyclic C6-20 aryl group; each R7 and R8 is —OR11 or —C(CF3)2OR11 where each R11 is H, a fluorinated or non-fluorinated C5-30 acid decomposable group, or a combination; each R9 is independently F, a C1-10 alkyl, C1-10 fluoroalkyl, C1-10 alkoxy, or a C1-10 fluoroalkoxy group; R10 is a cation-bound C10-40 photoacid generator-containing group, mole fractions a, b, and d are 0 to 0.80, c is 0.01 to 0.80, e is 0 to 0.50 provided where a, b, and d are 0, e is greater than 0, the sum a+b+c+d+e is 1, l and m are integers of 1 to 4, and n is an integer of 0 to 5. A photoresist and coated substrate, each include the copolymer.
    Type: Grant
    Filed: November 17, 2011
    Date of Patent: April 22, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: James W. Thackeray, Emad Aqad, Su Jin Kang, Owendi Ongayi