Sulfur Compound Containing Patents (Class 430/921)

Cross-Reference Art Collections

Sulfur in heterocyclic ring (Class 430/922)
  • 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
  • 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: 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: 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: 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: 8785106
    Abstract: A resist composition including: a base component (A) that exhibits changed solubility in a developing solution by the action of acid; a photoreactive quencher (C); and an acid generator component (B) that generates acid upon exposure, wherein the photoreactive quencher (C) contains a compound (C) represented by general formula (c1) shown below. In the formula, X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent; R1 represents a divalent linking group; R2 represents an arylene group which may have a substituent, and each of R3 and R4 independently represents an aryl group which may have a substituent; R3 and R4 may be mutually bonded with the sulfur atom to form a ring; R5 represents a hydroxy group, a halogen atom, an alkyl group of 1 to 5 carbon atoms, an alkoxy group or a fluorinated alkyl group; p represents an integer of 0 to 2; and q represents an integer of 0 to 3.
    Type: Grant
    Filed: February 21, 2013
    Date of Patent: July 22, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshitaka Komuro, Toshiaki Hato
  • Patent number: 8785105
    Abstract: A sulfonium salt having a 4-fluorophenyl group is introduced as recurring units into a polymer comprising hydroxyphenyl (meth)acrylate units and acid labile group-containing (meth)acrylate units to form a polymer which is useful as a base resin in a resist composition. The resist composition has a high sensitivity, high resolution and minimized LER.
    Type: Grant
    Filed: November 9, 2011
    Date of Patent: July 22, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama
  • 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: 8765353
    Abstract: A resist composition includes: a crosslinking material that is crosslinked in the presence of an acid; an acid amplifier; and a solvent.
    Type: Grant
    Filed: September 21, 2011
    Date of Patent: July 1, 2014
    Assignee: Sony Corporation
    Inventors: Koji Arimitsu, Nobuyuki Matsuzawa, Isao Mita
  • 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: 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: 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: 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: 8735044
    Abstract: 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: Grant
    Filed: May 25, 2010
    Date of Patent: May 27, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Isao Yoshida
  • 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: 8722306
    Abstract: A radiation-sensitive resin composition includes a resin (A1) that includes a repeating unit shown by the following formula (1-1) and a repeating unit shown by the following formula (1-2), and a radiation-sensitive acid generator (B). The radiation-sensitive resin composition exhibits excellent sensitivity, and can reduce a mask error factor (MEEF). wherein R1, R2, and R3 individually represent a linear or branched alkyl group having 1 to 4 carbon atoms, R4 represents a hydrogen atom, a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched fluoroalkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 4 carbon atoms, and q represents an integer from 0 to 3.
    Type: Grant
    Filed: May 26, 2008
    Date of Patent: May 13, 2014
    Assignee: JSR Corporation
    Inventors: Hirokazu Sakakibara, Makoto Shimizu, Takehiko Naruoka, Tomoki Nagai, Yoshifumi Oizumi
  • 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: 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: 8703387
    Abstract: A resist composition comprising a base component (A) which exhibits changed solubility in a developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) comprising an acid generator (B1) composed of a compound represented by general formula (b1-1) shown below [wherein, X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent, provided that a ring skelton of the cyclic group contains an —SO2— bond or an —O—SO2— bond, and at least one carbon atom which is not adjacent to the —SO2— bond or the —O—SO2— bond has an oxygen atom as a substituent; Q1 represents a divalent linking group or a single bond; Y1 represents an alkylene group which may have a substituent or a fluorinated alkylene group which may have a substituent; and A+ represents an organic cation].
    Type: Grant
    Filed: May 23, 2012
    Date of Patent: April 22, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi
  • 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
  • Patent number: 8691490
    Abstract: There is disclosed a sulfonium salt represented by the following general formula (1). In the formula, X and Y each represents a group having a polymerizable functional group; Z represents a divalent hydrocarbon group having 1 to 33 carbon atoms optionally containing a hetero atom; R1 represents a divalent hydrocarbon group having 1 to 36 carbon atoms optionally containing a hetero atom; and R2 and R3 each represents a monovalent hydrocarbon group having 1 to 30 carbon atoms optionally containing a hetero atom or R2 and R3 may be bonded with each other to form a ring together with a sulfur atom in the formula. There can be provided a sulfonium salt usable as a resist composition providing high resolution and excellent in LER in photolithography using a high energy beam such as an ArF excimer laser, an EUV light and an electron beam as a light source, a polymer obtained from the sulfonium salt, a resist composition containing the polymer and a patterning process using the resist composition.
    Type: Grant
    Filed: January 25, 2011
    Date of Patent: April 8, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Satoshi Watanabe, Youichi Ohsawa, Keiichi Masunaga, Takeshi Kinsho
  • Patent number: 8685619
    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, R23, R24, R25, X21 and Z1+ are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: April 1, 2014
    Assignee: Sumitomo Chemcial Company, Limited
    Inventors: Koji Ichikawa, Yuichi Mukai, Satoshi Yamamoto
  • Patent number: 8685616
    Abstract: The present invention provides photoacid generators for use in chemically amplified resists and lithographic processes using the same.
    Type: Grant
    Filed: June 10, 2009
    Date of Patent: April 1, 2014
    Assignee: University Of North Carolina At Charlotte
    Inventors: Kenneth E. Gonsalves, Mingxing Wang
  • Patent number: 8663900
    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, 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: March 4, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
  • Patent number: 8663899
    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, wherein R1, A1, R2, Rb1, Rb2, Lb1, ring Wb1, Rb3, Rb4, and Z1+ are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: March 4, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takashi Hiraoka, Hiromu Sakamoto
  • Patent number: 8663901
    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: March 4, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8652754
    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, Q1 and Q2, L1, ring W, Rf1 and Rf2, n and Z+are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: February 18, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takashi Hiraoka, Mitsuyoshi Ochiai
  • Patent number: 8652753
    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), an acid generator, and a salt having an anion represented by the formula (IA). wherein R1, A1, A13, X12, A14, R1A and R2A are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: February 18, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Tatsuro Masuyama, Satoshi Yamaguchi
  • Patent number: 8642253
    Abstract: 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: Grant
    Filed: November 8, 2010
    Date of Patent: February 4, 2014
    Assignee: FUJIFILM Incorporated
    Inventor: Hideaki Tsubaki
  • Patent number: 8632945
    Abstract: A radiation-sensitive resin composition includes a solvent and a polymer. The polymer includes a repeating unit represented by a formula (I), a repeating unit represented by a formula (II), or a both thereof. Each of R1 to R3 independently represents a hydroxyl group, or the like. At least one of R1 represents a group having two or more heteroatoms. l is an integer from 1 to 5. Each of m and n is independently an integer from 0 to 5. Each of R7 and R11 independently represents a hydrogen atom, or the like. Each of R8 to R10 independently represents a hydrogen atom, or the like. A represents —O—, or the like. D represents a substituted or unsubstituted methylene group, or the like.
    Type: Grant
    Filed: May 24, 2012
    Date of Patent: January 21, 2014
    Assignee: JSR Corporation
    Inventor: Ken Maruyama
  • Patent number: 8632939
    Abstract: 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: Grant
    Filed: February 25, 2011
    Date of Patent: January 21, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Keiichi Masunaga, Satoshi Watanabe, Jun Hatakeyama, Youichi Ohsawa, Daisuke Domon
  • Patent number: 8628908
    Abstract: 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: Grant
    Filed: February 28, 2012
    Date of Patent: January 14, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Tomohiro Kobayashi, Masayoshi Sagehashi, Takeshi Nagata, Youichi Ohsawa, Ryosuke Taniguchi
  • Patent number: 8628909
    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: January 14, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8628910
    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: January 14, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8623584
    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: January 7, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8617791
    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: December 31, 2013
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8617786
    Abstract: The present invention relates to compositions comprising poly-oxycarbosilane and methods for using the compositions in step and flash imprint lithography. The imprinting compositions comprise a poly-oxycarbosilane polymer, a silanol, a reaction initiator and optionally a pore generator.
    Type: Grant
    Filed: February 11, 2011
    Date of Patent: December 31, 2013
    Assignee: International Business Machines Corporation
    Inventors: Richard Anthony Dipietro, Geraud Jean-Michel Dubois, Robert Dennis Miller, Ratnam Sooriyakumaran
  • Patent number: 8617785
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes: (A) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (B) a resin capable of increasing a dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure; and (D) a low molecular compound having a group capable of leaving by an action of an acid, and a pattern forming method uses the composition.
    Type: Grant
    Filed: January 15, 2010
    Date of Patent: December 31, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Shuhei Yamaguchi
  • Patent number: 8614047
    Abstract: Provided are novel symmetrical and asymmetrical bifunctional photodecomposable bases (PDBs) with dicarboxylate anion groups that show increased imaging performance. Also provided are photoresist compositions prepared with the bifunctional dicarboxylated PDBs and lithography methods that use the photoresist compositions of the present invention.
    Type: Grant
    Filed: August 26, 2011
    Date of Patent: December 24, 2013
    Assignees: International Business Machines Corporation, JSR Corporation
    Inventors: Ramakrishnan Ayothi, William D. Hinsberg, Sally A. Swanson, Gregory M. Wallraff
  • Patent number: 8614046
    Abstract: 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: Grant
    Filed: July 9, 2010
    Date of Patent: December 24, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Yuko Yamashita
  • Patent number: 8609317
    Abstract: 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: Grant
    Filed: July 9, 2010
    Date of Patent: December 17, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Yuko Yamashita
  • Patent number: 8609891
    Abstract: New photoacid generator compounds are provided that comprise a nitrogen-base functional component of the structure —C(?O)N<. Photoresist compositions also are provided that comprise one or more PAGs of the invention.
    Type: Grant
    Filed: April 27, 2011
    Date of Patent: December 17, 2013
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Young Cheol Bae, Thomas Cardolaccia, Yi Liu