Polyolefin Or Halogen Containing Patents (Class 430/907)
  • Patent number: 9034558
    Abstract: Provided is an actinic-ray- or radiation-sensitive resin composition including (A) a compound that when exposed to actinic rays or radiation, generates an acid, (B) a resin that when acted on by an acid, increases its rate of dissolution in an alkali developer, and (C) a hydrophobic resin, wherein the hydrophobic resin (C) contains a repeating unit derived from any of monomers of general formula (1) below.
    Type: Grant
    Filed: September 28, 2011
    Date of Patent: May 19, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Shuhei Yamaguchi, Akinori Shibuya, Yusuke Iizuka
  • Patent number: 9023576
    Abstract: A positive resist composition for immersion exposure comprises: (A) a resin containing at least one repeating unit having a fluorine atom and increasing a solubility of the resin in an alkali developer by an action of an acid; and (B) a compound capable of generating an acid upon irradiation with one of an actinic ray and radiation.
    Type: Grant
    Filed: November 2, 2010
    Date of Patent: May 5, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Haruki Inabe, Shinichi Kanna, Hiromi Kanda
  • Patent number: 8999622
    Abstract: A pattern forming method, includes: (i) forming a film from a chemical amplification resist composition that contains (A) a resin capable of increasing a polarity of the resin (A) to decrease a solubility of the resin (A) for a developer containing an organic solvent by an action of an acid, (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a solvent; (ii) exposing the film; and (iii) performing development by using a developer containing an organic solvent, wherein the resin (A) has a structure in which a polar group is protected with a leaving group capable of decomposing and leaving by an action of an acid, and the leaving group contains a fluorine atom.
    Type: Grant
    Filed: December 28, 2012
    Date of Patent: April 7, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Kaoru Iwato, Shohei Kataoka
  • 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: 8968979
    Abstract: A positive resist composition comprises a polymer comprising repeat units having formula (1) or (2). Herein denotes an aromatic hydrocarbon group, R1 is H, methyl or trifluoromethyl, R2 is H, C1-C12 alkyl or aromatic hydrocarbon group, R3 is C1-C12 alkyl, or R2 and R3 may bond together to form a ring, and a is 1 or 2. When used in the ArF lithography, the resist composition exhibits high resolution. When used in the EB image writing for mask processing, the resist composition exhibits high resolution and sensitivity sufficient to comply with high-accelerating-voltage EB irradiation, and high etch resistance.
    Type: Grant
    Filed: November 20, 2009
    Date of Patent: March 3, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuya Takemura, Keiichi Masunaga, Daisuke Domon, Masayoshi Sagehashi
  • 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: 8945808
    Abstract: Resist compositions that can be used in immersion lithography without the use of an additional topcoat are disclosed. The resist compositions comprise a photoresist polymer, at least one photoacid generator, a solvent; and a self-topcoating resist additive. A method of forming a patterned material layer on a substrate using the resist composition is also disclosed.
    Type: Grant
    Filed: April 28, 2006
    Date of Patent: February 3, 2015
    Assignee: International Business Machines Corporation
    Inventors: Robert Allen David, Phillip Joe Brock, Carl E Larson, Daniel Paul Sanders, Ratnam Sooriyakumaran, Linda Karin Sundberg, Hoa D Truong, Gregory Michael Wallraff
  • 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: 8900788
    Abstract: A resist composition for immersion exposure, including: a base component (A) which exhibits changed solubility in an alkali developing solution under action of an acid, and contains no structural unit (c1) represented by the general formula (c1-1) shown below; an acid generator component (B) which generates an acid upon exposure; and a fluorine-containing resin component (C) which contains the structural unit (c1) (in the formula (c1-1), R represents a hydrogen atom, a lower alkyl group, a halogen atom, or a halogenated lower alkyl group; Rf represents a fluorinated alkyl group; and Y0 represents an alkylene group).
    Type: Grant
    Filed: October 12, 2007
    Date of Patent: December 2, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Yasuhiro Yoshii
  • Patent number: 8900789
    Abstract: An actinic-ray- or radiation-sensitive resin composition comprises (A) a resin that when acted on by an acid, exhibits an increased solubility in an alkali developer, (B) a compound that when exposed to actinic rays or radiation, generates an acid, (C) a resin containing two or more resins (c) each having at least either a fluorine atom or a silicon atom, and (D) a solvent.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: December 2, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hiroshi Saegusa, Shinichi Kanna
  • Patent number: 8895229
    Abstract: A composition for formation of upper layer film, which is used for forming an upper layer film on the surface of a photoresist film and which comprises a resin (A) having a repeating unit represented by the following general formula (1-1) and not having a repeating unit represented by the following general formula (1-2), and a resin (B) having a repeating unit represented by the following general formula (1-2) and not having a repeating unit represented by the following general formula (1-1). [In the general formulas (1-1) and (1-2), R1 is hydrogen or the like; R2 is single bonds or the like; and R3 is a fluorine-substituted, linear or branched alkyl group having 1 to 12 carbon atoms, or the like.] The composition can form an upper layer film giving a sufficiently high receded contact angle.
    Type: Grant
    Filed: October 11, 2007
    Date of Patent: November 25, 2014
    Assignee: JSR Corporation
    Inventors: Yukio Nishimura, Norihiko Sugie, Hiromitsu Nakashima, Norihiro Natsume, Daita Kouno
  • Patent number: 8877421
    Abstract: A positive resist composition includes: (A) a resin capable of increasing the solubility in an alkali developing solution by the action of an acid, including: (a1) a repeating unit selected from repeating units represented by following formulae (a1-1) to (a1-3); (a2) a repeating unit represented by a following formula (a2); and (a3) a repeating unit selected from repeating units represented by following formulae (a3-1) to (a3-4); (B) a compound capable of generating an acid upon irradiation with actinic ray or radiation; (C) a resin having at least one of a fluorine atom and a silicon atom, and being insoluble in an alkali developing solution; and (D) a solvent, wherein the formulae above are defined in the specification.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: November 4, 2014
    Assignee: FUJIFILM Corporation
    Inventor: Shinichi Kanna
  • Patent number: 8859187
    Abstract: A novel method of forming a resist pattern in which thickness loss from the resist pattern is reduced, and a negative resist composition that can be used in this method of forming a resist pattern. The method of forming a resist pattern includes: forming a first resist film by applying a first resist composition to a support, forming a first resist pattern by selectively exposing the first resist film through a first mask pattern and then developing the first resist film, forming a second resist film by applying a negative resist composition containing an ether-based organic solvent (S?) having no hydroxyl groups onto the support having the first resist pattern formed thereon, and forming a resist pattern by selectively exposing the second resist film through a second mask pattern and then developing the second resist film.
    Type: Grant
    Filed: October 19, 2007
    Date of Patent: October 14, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Ken Tanaka, Sho Abe, Shigeru Yokoi
  • 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: 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: 8802349
    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, the resin containing (a) a repeating unit represented by the following formula (AN-01), (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a resin that contains at least either a fluorine atom or a silicon atom and contains a repeating unit having a group capable of decomposing by the action of an alkali developer to increase the solubility in an alkali developer: wherein the variables in formula (AN-01) are defined in the description.
    Type: Grant
    Filed: March 31, 2010
    Date of Patent: August 12, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Masahiro Yoshidome, Shuji Hirano, Hiroshi Saegusa, Kaoru Iwato, 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: 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: 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: 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: 8778594
    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 compound represented by the formula (II), wherein R1, A1, A13, A14, X12, R23, R24, R25, R26, X21 and X22 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: July 15, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Yuichi Mukai
  • 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: 8771921
    Abstract: A negative resist composition including an alkali-soluble resin component (A), an acid generator component (B) that generates acid upon exposure, and a cross-linking component (C), the alkali-soluble resin component (A) including a polymeric compound (F) having a structural unit (f1) containing a base dissociable group and a structural unit (f2) containing a cross-linking group-containing group.
    Type: Grant
    Filed: March 2, 2012
    Date of Patent: July 8, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Abe Sho, Shiono Daiju, Hirano Tomoyuki, Dazai Takahiro
  • Patent number: 8748078
    Abstract: A cyclic compound represented by formula (1): wherein L, R1, R?, and m are as defined in the specification. The cyclic compound of formula (1) is highly soluble to a safety solvent, highly sensitive, and capable of forming resist patterns with good profile. Therefore, the cyclic compound is useful as a component of a radiation-sensitive composition.
    Type: Grant
    Filed: August 30, 2010
    Date of Patent: June 10, 2014
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hiromi Hayashi, Masatoshi Echigo, Dai Oguro
  • 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: 8741554
    Abstract: A pattern is formed by coating a first positive resist composition comprising a base resin, a photoacid generator, and a base generator onto a substrate to form a first resist film, patternwise exposure, PEB, and development to form a first resist pattern, heating the first resist pattern for causing the base generator to generate a base for inactivating the pattern to acid, coating a second positive resist composition comprising a C3-C8 alcohol and an optional C6-C12 ether onto the first resist pattern-bearing substrate to form a second resist film, patternwise exposure, PEB, and development to form a second resist pattern.
    Type: Grant
    Filed: May 26, 2010
    Date of Patent: June 3, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Kazuhiro Katayama, Youichi Ohsawa, Masaki Ohashi
  • 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: 8728707
    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 compound represented by the formula (II), wherein R1, A1, A13, A14, X12, R23 and ring W21 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: May 20, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi
  • Patent number: 8722825
    Abstract: A polymer comprises the polymerized product of monomers comprising a nitrogen-containing monomer comprising formula (Ia), formula (Ib), or a combination of formulas (Ia) and (Ib), and an acid-deprotectable monomer having the formula (II): wherein a is 0 or 1, each Ra is independently H, F, C1-10 alkyl, or C1-10 fluoroalkyl, L1 is a straight chain or branched C1-20 alkylene group, or a monocyclic, polycyclic, or fused polycyclic C3-20 cycloalkylene group, each Rb is independently H, C1-10 alkyl, C3-20 cycloalkyl, C3-20 heterocycloalkyl, an aliphatic C5-20 oxycarbonyl, or a C1-30 acyl group optionally including a heteroatom substituent group, where each Rb is separate or at least one Rb is attached to an adjacent Rb; LN is a nitrogen-containing monocyclic, polycyclic, or fused polycyclic C3-20 heterocycloalkylene group, and X is H, C1-10 alkyl, aliphatic C5-20 oxycarbonyl, or a C1-30 acyl group optionally including a heteroatom substituent group; and each Rc is independently C1-10 alkyl, C3-20 cycloalkyl, o
    Type: Grant
    Filed: May 29, 2012
    Date of Patent: May 13, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Deyan Wang, Chunyi Wu, Cong Liu, Gerhard Pohlers, Cheng-bai Xu, George G. Barclay
  • Patent number: 8715919
    Abstract: Lithography methods on a semiconductor substrate are described. The methods include coating a resist layer on the substrate, wherein the resist layer comprises a resist polymer configured to turn soluble to a base solution in response to reaction with an acid, and a switchable polymer that includes a base soluble polymer having a carboxylic acid, hydroxyl, lactone, or anhydride functional group, performing a pre-exposure bake on the resist layer, exposing the resist-coated substrate, and developing the exposed substrate with a developing solution.
    Type: Grant
    Filed: August 20, 2013
    Date of Patent: May 6, 2014
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Ching-Yu Chang, Chih-Cheng Chiu
  • 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: 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: 8697329
    Abstract: A positive resist composition, which comprises: (A) a resin of which solubility in an alkali developer increases under an action of an acid; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (C) a resin having at least one of a fluorine atom and a silicon atom; and (D) a solvent, wherein the resin (C) contains at least one of: (C1) a resin having at least one of a fluorine atom and a silicon atom and having an alicyclic structure; and (C2) a resin containing a repeating unit having at least one of a fluorine atom and a silicon atom in a side chain and a repeating unit having an unsubstituted alkyl group in a side chain; and a pattern forming method.
    Type: Grant
    Filed: March 11, 2008
    Date of Patent: April 15, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hiromi Kanda, Shinichi Kanna
  • Patent number: 8685618
    Abstract: A resist composition having; (A1) a resin having a structural unit represented by the formula (I), (A2) a resin having a structural unit represented by the formula (II) and 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 (B) an acid generator. wherein R1, A1, A13, X12, A14, R3 and ring X1 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: April 1, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Akira Kamabuchi
  • 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: 8685620
    Abstract: A resist composition including 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 base component (A) containing a polymeric compound (A1) having a structural unit (a5) represented by general formula (a5-0) shown below (R1 represents a sulfur atom or an oxygen atom; R2 represents a single bond or a divalent linking group; and Y represents an aromatic hydrocarbon group or an aliphatic hydrocarbon group having a polycyclic group, provided that the aromatic hydrocarbon group or the aliphatic hydrocarbon may have a carbon atom or a hydrogen atom thereof substituted with a substituent.
    Type: Grant
    Filed: November 6, 2012
    Date of Patent: April 1, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daichi Takaki, Daiju Shiono, Yoshiyuki Utsumi, Takaaki Kaiho
  • Patent number: 8679724
    Abstract: A positive resist composition comprises: (A) a resin of which solubility in an alkali developer increases under an action of an acid; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (C) a resin having at least one of a fluorine atom and a silicon atom; and (D) a solvent; and a pattern forming method using the positive resist composition.
    Type: Grant
    Filed: December 11, 2006
    Date of Patent: March 25, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hiromi Kanda, Shinichi Kanna
  • 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: 8663897
    Abstract: According to the present invention, there is provided a polymerizable fluorine-containing sulfonic acid onium salt of the following general formula (2) and a resin obtained by polymerization thereof. It is possible by the use of this sulfonate resin of the present invention to provide a resist composition with high resolution, board depth of focus tolerance (DOF), small line edge roughness (LER) and high sensitivity. In the formula, Z represents a substituted or unsubstituted C1-C6 straight or branched alkylene group, or a divalent moiety in which substituted or unsubstituted C1-C6 straight or branched alkylene groups are bonded in series to a divalent group obtained by elimination of two hydrogen atoms from an alicyclic or aromatic hydrocarbon; R represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl or fluorine-containing alkyl group; and Q+ represents a sulfonium cation or an iodonium cation.
    Type: Grant
    Filed: October 8, 2009
    Date of Patent: March 4, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Takashi Masubuchi, Kazunori Mori, Yuji Hagiwara, Satoru Narizuka, Kazuhiko Maeda
  • 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: 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: 8652751
    Abstract: A resist composition, which contains: a silicon compound having at least an alkyl-soluble group which may be substituted with a substituent; and a resin having an alkali-soluble group which may be substituted with an acid labile group, wherein the resist composition is designed to be subjected to immersion lithography.
    Type: Grant
    Filed: September 10, 2009
    Date of Patent: February 18, 2014
    Assignee: Fujitsu Limited
    Inventors: Miwa Kozawa, Koji Nozaki
  • 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: 8647808
    Abstract: A fluorinated monomer has formula (1) wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are H or a monovalent hydrocarbon group, R4 to R6 each are a monovalent fluorinated hydrocarbon group, A is a divalent hydrocarbon group, and k1 is 0, 1 or 2. A polymer derived from the fluorinated monomer may be endowed with appropriate water repellency, water slip, acid lability and hydrolysis and is useful as an additive polymer in formulating a resist composition.
    Type: Grant
    Filed: April 6, 2011
    Date of Patent: February 11, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayoshi Sagehashi, Koji Hasegawa, Takeshi Sasami
  • 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: 8609321
    Abstract: A radiation-sensitive resin composition includes a polymer having a structural unit represented by a formula (I). In the formula (I), R1 represents a hydrogen atom or a methyl group. X represents a bivalent alicyclic hydrocarbon group not having or having a substituent. Y represents a bivalent hydrocarbon group having 1 to 20 carbon atoms. R2 represents a methyl group or a trifluoromethyl group.
    Type: Grant
    Filed: March 8, 2013
    Date of Patent: December 17, 2013
    Assignee: JSP Corporation
    Inventors: Hiromitsu Nakashima, Reiko Kimura, Kazuo Nakahara, Mitsuo Sato
  • Patent number: 8592132
    Abstract: A resist composition includes (A1) a resin having a structural unit represented by the formula (I), (A2) a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and (B) an acid generator having an acid-labile group. wherein R1 represents a hydrogen atom or a methyl group; A1 represents a C1 to C6 alkanediyl group; R2 represents a C1 to C10 hydrocarbon group having a fluorine atom.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: November 26, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi, Yuki Suzuki