Polyolefin Or Halogen Containing Patents (Class 430/907)
  • Patent number: 8148043
    Abstract: Silsesquioxane-based compositions that contain (a) silsesquioxane resins that contain HSiO3/2 units and RSiO3/2 units wherein; R is an acid dissociable group, and (b) least one organic base additive selected from bulky tertiary amines, imides, amides and the polymeric amines wherein the organic base additive contains an electron-attracting group with the provision that the organic base additive is not 7-diethylamino-4-methylcoumarin. The silsesquioxane-based compositions are useful as positive resist compositions in forming patterned features on substrate, particularly useful for multi-layer layer (i.e. bilayer) 193 nm & 157 nm photolithographic applications.
    Type: Grant
    Filed: June 27, 2007
    Date of Patent: April 3, 2012
    Assignee: Dow Corning Corporation
    Inventors: Sanlin Hu, Eric Scott Moyer
  • Patent number: 8142979
    Abstract: A resist composition for immersion exposure, including a base component (A) that exhibits changed solubility in an alkali developing solution under action of acid, an acid generator component (B) that generates acid upon exposure, and a fluorine-containing compound (C) represented by general formula (c-1) (in formula (c-1), R1 represents an organic group which may contain a polymerizable group; X represents a divalent organic group having an acid dissociable portion; and R2 represents an organic group having a fluorine atom).
    Type: Grant
    Filed: June 10, 2009
    Date of Patent: March 27, 2012
    Assignee: Tokyo Ohka Tokyo Co., Ltd.
    Inventors: Tsuyoshi Kurosawa, Hiroaki Shimizu
  • Patent number: 8124314
    Abstract: A radiation-sensitive composition includes (A) a first polymer which becomes alkali-soluble by the action of an acid and does not contain a fluorine atom, (B) a second polymer having a repeating unit (b1) shown by the following formula (1) and a fluorine-containing repeating unit (b2), and (C) a radiation-sensitive acid generator, the content of the second polymer (B) in the composition being 0.1 to 20 parts by mass relative to 100 parts by mass of the first polymer (A). wherein R1 represents a monovalent organic group, and R8 represents a linear or branched alkyl group having 1 to 12 carbon atoms. The composition can form a resist film capable of suppressing defects inherent to liquid immersion lithography such as watermark defects and bubble defects.
    Type: Grant
    Filed: April 1, 2010
    Date of Patent: February 28, 2012
    Assignee: JSR Corporation
    Inventors: Yukio Nishimura, Hiromu Miyata
  • Patent number: 8110334
    Abstract: A radiation-sensitive composition containing a resist compound having a high sensitivity, a high resolution, a high etching resistance, and a low outgas which forms a resist pattern with a good shape is described. Further described is a method of forming a resist pattern using the radiation-sensitive composition. Still further described are a novel composition for forming a photoresist under coat film which is excellent in optical properties and etching resistance and contains substantially no sublimable substance and an under coat film formed by the composition.
    Type: Grant
    Filed: November 1, 2007
    Date of Patent: February 7, 2012
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masatoshi Echigo, Dai Oguro
  • Patent number: 8110339
    Abstract: Multi-tone resists can enhance the resolution limit of a lithographic process by advantageously using the changeable solubility of a resist composition as a function of lithographic radiation dosage. By imaging a multi-tone resist with different doses of lithographic radiation in a selected pattern, the pattern can be imparted to the resist upon subsequent development of the resist. In some aspects, a resist composition is utilized having an aliphatic polymer (e.g., a copolymer with fluoropolymer units and/or methacrylate units) with acid labile groups and a plurality of crosslinkable groups that can be crosslinked to other portions of the aliphatic polymer. Other components such as base generators and/or crosslinking agents can also be included. Such compositions can be useful in extending the resolution of UV lithographic radiation processes (e.g., wavelengths less than 200 nm). Other aspects of such compositions and methods are also discussed.
    Type: Grant
    Filed: April 17, 2008
    Date of Patent: February 7, 2012
    Assignee: Massachusetts Institute of Technology
    Inventor: Theodore H. Fedynyshyn
  • Patent number: 8110336
    Abstract: A resin comprising a structural unit represented by the formula (I): wherein Q1 and Q2 represent a fluorine atom etc., U represents a C1-C20 divalent hydrocarbon group in which one or more —CH2— may be replaced by —O— etc., X1 represents —O—CO— etc., and A+ represents an organic counter ion.
    Type: Grant
    Filed: September 18, 2009
    Date of Patent: February 7, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ichiki Takemoto, Nobuo Ando
  • Patent number: 8105748
    Abstract: A polymerizable anion-containing sulfonium salt having formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2, R3 and R4 are C1-C10 alkyl, alkenyl or oxoalkyl or C6-C18 aryl, aralkyl or aryloxoalkyl, or two of R2, R3 and R4 may bond together to form a ring with S, A is a C2-C20 hydrocarbon group having cyclic structure, and n is 0 or 1. The sulfonium salt generates a very strong sulfonic acid upon exposure to high-energy radiation. A resist composition comprising a polymer derived from the sulfonium salt is also provided.
    Type: Grant
    Filed: October 16, 2009
    Date of Patent: January 31, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Youichi Ohsawa, Takeshi Kinsho, Jun Hatakeyama, Seiichiro Tachibana
  • Patent number: 8105747
    Abstract: A positive resist composition including a resin component (A) which exhibits changed alkali solubility under action of acid and an acid-generator component (B) which generates acid upon exposure, the resin component (A) including a copolymer (A1) containing a structural unit (a1) represented by general formula (II) or a polymer (A2) consisting of a structural unit (a1) represented by general formula (II) (wherein R represents a hydrogen atom, a halogen atom, a lower alkyl group or a halogenated lower alkyl group; each of R1 to R3 independently represents an alkyl group or a fluorinated alkyl group, with the provision that no fluorine atom is bonded to a carbon atom adjacent to the tertiary carbon atom to which R1 to R3 are bonded, and at least one of R1 to R3 represents a fluorinated alkyl group; and R2 and R3 may form a ring structure).
    Type: Grant
    Filed: October 15, 2007
    Date of Patent: January 31, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Hiroaki Shimizu, Kyoko Ohshita, Yasuhiro Yoshii
  • Patent number: 8088556
    Abstract: To provide a thiopyran derivative, having a structure expressed by the following general formula 1: where X is O or S; R1 is —H, —CH3, C2-4 alkyl group, thioether group, or ketone group; R2 is —H, —CH3, or trifluoromethyl group; and R1 and R2 may be identical to or different from each other.
    Type: Grant
    Filed: May 19, 2010
    Date of Patent: January 3, 2012
    Assignee: Fujitsu Limited
    Inventor: Koji Nozaki
  • Patent number: 8062830
    Abstract: The present invention provides a chemically amplified resist composition comprising: a resin (A) which contains no fluorine atom and a structural unit (a1) having an acid-labile group in a side chain, a resin (B) which contains a structural unit (b2) having a fluorine-containing group in a side chain and at least one structural unit selected from the group consisting of a structural unit (b1) having an acid-labile group, a structural unit (b3) having a hydroxyl group and a structural unit (b4) having a lactone structure in a side chain, and an acid generator, wherein the content of the structural unit (b1) based on the total units of the resin (B) is less than 10 mol %.
    Type: Grant
    Filed: April 17, 2009
    Date of Patent: November 22, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yusuke Fuji, Junji Shigematsu, Takayuki Miyagawa, Nobuo Ando, Ichiki Takemoto
  • Patent number: 8062828
    Abstract: A positive resist composition comprises a polymer comprising recurring units having a sulfonium salt incorporated therein as a base resin which becomes soluble in alkaline developer under the action of acid. The polymer generates a strong sulfonic acid upon exposure to high-energy radiation so as to facilitate effective scission of acid labile groups in the resist composition.
    Type: Grant
    Filed: February 13, 2009
    Date of Patent: November 22, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeshi Kinsho, Masaki Ohashi, Seiichiro Tachibana, Takeru Watanabe, Jun Hatakeyama
  • Patent number: 8057985
    Abstract: A polymerizable anion-containing sulfonium salt having formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2, R3 and R4 are C1-C10 alkyl, alkenyl or oxoalkyl or C6-C18 aryl, aralkyl or aryloxoalkyl, or two of R2, R3 and R4 may bond together to form a ring with S, A is a C1-C20 organic group, and n is 0 or 1. The sulfonium salt generates a very strong sulfonic acid upon exposure to high-energy radiation. A resist composition comprising a polymer derived from the sulfonium salt is also provided.
    Type: Grant
    Filed: August 27, 2009
    Date of Patent: November 15, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa, Jun Hatakeyama, Seiichiro Tachibana
  • Patent number: 8057983
    Abstract: The present invention provides a chemically amplified resist composition comprising: a resin (A) which contains no fluorine atom and a structural unit (a1) having an acid-labile group in a side chain, a resin (B) which contains a structural unit (b2) having a fluorine-containing group in a side chain and at least one structural unit selected from the group consisting of a structural unit (b1) having an acid-labile group, a structural unit (b3) having a hydroxyl group and a structural unit (b4) having a lactone structure in a side chain, and an acid generator, wherein the amount of the resin (B) is 2 parts by weight or less per 100 parts by weight of the resin (A).
    Type: Grant
    Filed: April 17, 2009
    Date of Patent: November 15, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yusuke Fuji, Junji Shigematsu, Takayuki Miyagawa, Nobuo Ando, Ichiki Takemoto
  • Patent number: 8057981
    Abstract: A polymer obtained through copolymerization of a monomer having a hexafluoroalcohol pendant and a monomer having a hexafluoroalcohol pendant whose hydroxyl moiety has been protected is useful as an additive to a photoresist composition and as a protective coating material for immersion lithography. When processed by immersion lithography, the resist composition and protective coating composition exhibit good water repellency and water slip and produce few development defects.
    Type: Grant
    Filed: February 13, 2009
    Date of Patent: November 15, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Kazunori Maeda, Tomohiro Kobayashi
  • Patent number: 8053172
    Abstract: Photolithography compositions and methods. A first layer of a first photoresist is formed on a substrate. A second layer of a second photoresist is formed directly onto the first layer. The second polymer of the second photoresist includes an absorbing moiety. The second layer is patternwise imaged and developed, resulting in removal of base-soluble regions. A relief pattern from the second layer remains. The relief pattern and the first layer are exposed to a second dose of the radiation. The polymer in the relief pattern absorbs a portion of the second dose. A fraction of the second dose passes through the at least one region of the relief pattern and exposes at least one region of the first layer. The relief pattern and base-soluble regions of the first layer are removed. A relief pattern from the first layer remains. A second photolithography method and a photoresist composition are also included.
    Type: Grant
    Filed: February 21, 2008
    Date of Patent: November 8, 2011
    Assignee: International Business Machines Corporation
    Inventors: Scott David Halle, Wu-Song Huang, Ranee Wai-Ling Kwong, Pushkara R. Varanasi
  • Patent number: 8053161
    Abstract: A resist composition comprises: (A) a resin capable of increasing its solubility in an alkali developer by action of an acid; (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 (D) a solvent, wherein the resin (C) has a degree of molecular weight dispersion of 1.3 or less and a weight average molecular weight of 1.0×104 or less.
    Type: Grant
    Filed: September 25, 2007
    Date of Patent: November 8, 2011
    Assignee: FUJIFILM Corporation
    Inventors: Kenji Wada, Hiroshi Saegusa
  • Patent number: 8053165
    Abstract: A hydroxyl-containing monomer of formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are monovalent C1-C15 hydrocarbon groups, or R2 and R3 may form an aliphatic ring. The monomers are useful for the synthesis of polymers which have high transparency to radiation of up to 500 nm and the effect of controlling acid diffusion so that the polymers may be used as a base resin to formulate radiation-sensitive resist compositions having a high resolution.
    Type: Grant
    Filed: March 17, 2009
    Date of Patent: November 8, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Masaki Ohashi, Koji Hasegawa, Takeru Watanabe
  • Patent number: 8043788
    Abstract: To a resist composition comprising a polymer which changes its alkali solubility under the action of an acid as a base resin, is added a copolymer comprising recurring units containing amino and recurring units containing ?-trifluoromethylhydroxy as an additive. The composition is suited for immersion lithography.
    Type: Grant
    Filed: July 2, 2008
    Date of Patent: October 25, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Kobayashi, Jun Hatakeyama, Yuji Harada
  • Patent number: 8039199
    Abstract: A negative resist composition for immersion exposure including a fluorine-containing polymeric compound (F) containing a structural unit having a base dissociable group, an alkali-soluble resin component (A) excluding the fluorine-containing polymeric compound (F), an acid generator component (B) that generates acid upon exposure, and a cross-linking component (C); and a method of forming a resist pattern including applying the negative resist composition for immersion exposure to a substrate to form a resist film, subjecting the resist film to immersion exposure, and subjecting the resist film to alkali developing to form a resist pattern.
    Type: Grant
    Filed: April 30, 2009
    Date of Patent: October 18, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Sho Abe
  • Patent number: 8034537
    Abstract: A positive photosensitive composition comprises: (A) a resin that has an acid decomposable repeating unit represented by formula (I) and increases its solubility in an alkali developer by action of an acid; (B) a compound that generates an acid in irradiation with actinic light or radiation; (C) a resin that has: at least one of a fluorine atom and a silicon atom; and a group selected from the group consisting of groups (x) to (z); and (D) a solvent: (x) an alkali soluble group, (y) a group which decomposes by action of an alkali developer and increases a solubility of the resin (C) in an alkali developer, and (z) a group which decomposes by action of an acid, wherein, Xa1 represents a hydrogen atom, an alkyl group, a cyano group or a halogen atom, Ry1 to Ry3 each independently represents an alkyl group or a cycloalkyl group, and at least two of Ry1 to Ry3 may be coupled to form a ring structure, and Z represents a divalent linking group.
    Type: Grant
    Filed: March 27, 2008
    Date of Patent: October 11, 2011
    Assignee: FUJIFILM Corporation
    Inventors: Toshiaki Fukuhara, Hiromi Kanda, Shinichi Kanna
  • Patent number: 8034534
    Abstract: The present invention relates to partially fluorinated (meth)acrylic polymers that can be blended with other (meth)acrylic polymers to provide enhanced surface properties.
    Type: Grant
    Filed: August 14, 2007
    Date of Patent: October 11, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: William Brown Farnham, Suniti Moudgil
  • Patent number: 8034532
    Abstract: A topcoat material for application on top of a photoresist material is disclosed. The topcoat material comprises an acid-inert compound. The topcoat material also comprises a polymer or an oligomer or a cage structure which shows negligible intermixing with the imaging layer and is soluble in aqueous base developer. A method of forming a patterned material layer on a substrate and a coated substrate comprising the topcoat material is also disclosed.
    Type: Grant
    Filed: April 28, 2006
    Date of Patent: October 11, 2011
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Phillip Joe Brock, Carl E. Larson, Ratnam Sooriyakumaran, Linda Karin Sundberg, Hoa D Truong
  • Patent number: 8029969
    Abstract: A photosensitive material for use in semiconductor manufacture comprises a copolymer that includes a plurality of photoresist chains and a plurality of hydrophobic chains, each hydrophobic chain attached to the end of one of the photoresist chains. The copolymer in response to externally applied energy will self-assemble to a photoresist layer and a hydrophobic layer.
    Type: Grant
    Filed: May 14, 2007
    Date of Patent: October 4, 2011
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Hsiao-Wei Yeh, Jen-Chieh Shih, Jian-Hong Chen
  • Patent number: 8026039
    Abstract: A radiation-sensitive resin composition includes a resin that includes a repeating unit shown by the following formula (1) and a solvent. The radiation-sensitive resin composition has an excellent performance as a radiation-sensitive acid generator, includes a resin that adversely affects the environment and a human body to only a small extent, and can form a resist film that has a high resolution and forms an excellent resist pattern. wherein R1 represents a hydrogen atom or the like, M+ represents a specific cation, and n represents an integer from 1 to 5.
    Type: Grant
    Filed: November 9, 2007
    Date of Patent: September 27, 2011
    Assignee: JSR Corporation
    Inventors: Tomoki Nagai, Takuma Ebata, Makoto Shimizu
  • Patent number: 8003296
    Abstract: The present invention provides a chemically amplified positive composition comprising: (A) a resin comprising a structural unit having an acid-labile group and being itself insoluble or poorly soluble in an alkali aqueous solution but becoming soluble in an alkali aqueous solution by the action of an acid, (B) a resin comprising a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group or a C1-C4 perfluoroalkyl group, Z represents a single bond or —(CH2)k—CO—X4—, k represents an integer of 1 to 4, X1, X2, X3 and X4 each independently represents an oxygen atom or a sulfur atom, m represents an integer of 1 to 3 and n represents an integer of 0 to 3, and a structural unit having a fluorine atom in a side chain, and an acid generator.
    Type: Grant
    Filed: August 5, 2009
    Date of Patent: August 23, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masahiko Shimada, Kazuhiko Hashimoto, Junji Shigematsu, Takayuki Miyagawa, Satoshi Yamamoto
  • Patent number: 7998654
    Abstract: A positive resist composition comprises: (A) a resin that has a repeating unit represented by general formula (a1) and increases its solubility in an alkali developer by action of an acid; (B) a compound which generates an acid upon irradiation with an actinic ray or a radiation; and (C) a resin that has at least one of a fluorine atom and a silicon atom and has a group selected from the group consisting of (x), (y) and (z); and (D) a solvent: (x) an alkali-soluble group; (y) a group capable that decomposes by action of an alkali developer to undergo an increase in a solubility of the resin (C) in an alkali developer; and (z) a group that decomposes by action of an acid, wherein R represents a hydrogen atom or a methyl group, Rxa represents an alkyl group or a cycloalkyl group, and n represents an integer of 1 to 8.
    Type: Grant
    Filed: March 27, 2008
    Date of Patent: August 16, 2011
    Assignee: FUJIFILM Corporation
    Inventors: Fumiyuki Nishiyama, Hiromi Kanda
  • Patent number: 7998656
    Abstract: The present invention provides a chemically amplified positive composition comprising: a resin comprising a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group or a C1-C4 perfluoroalkyl group, Z represents a single bond or —(CH2)k—CO—X4—, k represents an integer of 1 to 4, X1, X2, X3 and X4 each independently represents an oxygen atom or a sulfur atom, m represents an integer of 1 to 3 and n represents an integer of 0 to 3, and an acid generator.
    Type: Grant
    Filed: August 5, 2009
    Date of Patent: August 16, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masahiko Shimada, Kazuhiko Hashimoto, Satoshi Yamaguchi, Soon Shin Kim, Yoshiyuki Takata, Takashi Hiraoka
  • Patent number: 7985528
    Abstract: A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) an acid generator. The resin (A) is a polymer comprising recurring units containing a non-leaving hydroxyl group represented by formula (1) wherein R1 is H, methyl or trifluoromethyl, m is 1 or 2, and the hydroxyl group attaches to a tertiary carbon atom. The composition is improved in resolution when processed by lithography.
    Type: Grant
    Filed: August 27, 2009
    Date of Patent: July 26, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Takeshi Kinsho, Masaki Ohashi, Koji Hasegawa, Masashi Iio
  • Patent number: 7981589
    Abstract: Fluorinated monomers of formula (1) are useful in producing polymers for the formulation of radiation-sensitive resist compositions.
    Type: Grant
    Filed: June 25, 2008
    Date of Patent: July 19, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Takeshi Kinsho, Katsuhiro Kobayashi, Tsunehiro Nishi, Takeru Watanabe
  • Patent number: 7951524
    Abstract: Photoresist additive polymers and photoresist formulations that can be used in immersion lithography without the use of an additional topcoat. The resist compositions include a photoresist polymer, at least one photoacid generator, a solvent; and a photoresist additive polymer. Also a method of forming using photoresist formulations including photoresist additive polymers.
    Type: Grant
    Filed: January 31, 2008
    Date of Patent: May 31, 2011
    Assignees: International Business Machines Corporation, JSR Micro Inc.
    Inventors: Robert Allen, Phillip Brock, Shiro Kusumoto, Yukio Nishimura, Daniel P. Sanders, Mark Steven Slezak, Ratnam Sooriyakumaran, Linda K. Sundberg, Hoa Trung, Gregory M. Wallraff
  • Patent number: 7947421
    Abstract: A positive resist composition for immersion exposure comprising: (A) a resin having an alicyclic hydrocarbon structure, wherein the resin is capable of increasing a solubility of the resin (A) in an alkaline 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, wherein the resin (A) includes a component having a molecular weight of 1,000 or less in an area ration of 20% or less to an entire area in a pattern area by gel permeation chromatography, and a pattern-forming method using the same.
    Type: Grant
    Filed: January 20, 2006
    Date of Patent: May 24, 2011
    Assignee: FUJIFILM Corporation
    Inventor: Hiromi Kanda
  • Patent number: 7923195
    Abstract: The present invention provides a polymer suitable as a base resin for a positive resist composition, especially for a chemically amplified positive resist composition, having a high sensitivity, a high degree of resolution, a good pattern configuration after exposure, and in addition an excellent etching resistance; a positive resist composition using the polymer; and a patterning process. The positive resist composition of the present invention is characterized in that it contains at least, as a base resin, a polymer whose hydrogen atom of a phenolic hydroxide group is substituted by an acid labile group represented by the following general formula (1).
    Type: Grant
    Filed: January 22, 2009
    Date of Patent: April 12, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takanobu Takeda
  • Patent number: 7919225
    Abstract: A method and a composition. The composition includes at least one carbosilane-substituted silsesquioxane polymer which crosslinks in the presence of an acid. The at least one carbosilane-substituted silsesquioxane polymer is soluble in aqueous base. The method includes forming a coating on a substrate. The coating includes one or more carbosilane-substituted silsesquioxane polymers. The carbosilane-substituted silsesquioxane polymer is soluble in aqueous base. The coating is exposed to radiation, resulting in generating a latent pattern in the coating. The exposed coating is baked at a first temperature less than about 150° C. The baked coating is developed, resulting in forming a latent image from the latent pattern in the baked coating. The latent image is cured at a second temperature less than about 500° C.
    Type: Grant
    Filed: May 23, 2008
    Date of Patent: April 5, 2011
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Phillip Joe Brock, Blake W. Davis, Geraud Jean-Michel Dubois, Qinghuang Lin, Robert D. Miller, Alshakim Nelson, Sampath Purushothaman, Ratnam Sooriyakumaran
  • Patent number: 7906269
    Abstract: Disclosed is a fluorine-containing polymer compound containing first and second repeating units respectively represented by formulas (a-1) and (a-2), wherein R3 represents a fluorine atom or fluorine-containing alkyl group, each of W and W1 independently represents a bivalent linking group, R2 represents an acid-labile protecting group, each of R4, R5 and R6 independently represents a hydrogen atom, fluorine atom or monovalent organic group, and at least two of R4, R5, R6 and W or W1 may be combined to form a cyclic structure in formula (a-1) or (a-2). This polymer compound has a weight-average molecular weight of 1,000 to 1,000,000 and can provide a resist composition capable of forming a pattern with no swelling and no pattern falling down.
    Type: Grant
    Filed: August 28, 2008
    Date of Patent: March 15, 2011
    Assignee: Central Glass Company, Limited
    Inventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiro Yamanaka
  • Patent number: 7906268
    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: March 11, 2005
    Date of Patent: March 15, 2011
    Assignee: FUJIFILM Corporation
    Inventors: Haruki Inabe, Shinichi Kanna, Hiromi Kanda
  • Patent number: 7887988
    Abstract: A resist composition, which comprises: (A) a resin containing a repeating unit represented by formula (I); and (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation: wherein AR represents a benzene ring or a naphthalene ring; R represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group; Z represents a linking group for forming a ring together with AR; and A represents an atom or group selected from the group consisting of a hydrogen atom, an alkyl group, a halogen atom, a cyano group and an alkyloxycarbonyl group, and a pattern forming method using the resist composition.
    Type: Grant
    Filed: March 14, 2007
    Date of Patent: February 15, 2011
    Assignee: FUJIFILM Corporation
    Inventors: Kazuyoshi Mizutani, Kaoru Iwato, Kunihiko Kodama, Masaomi Makino
  • Patent number: 7887990
    Abstract: Disclosed is a fluorine-containing compound represented by formula (1), wherein R1 represents a polymerizable double-bond containing group, R2 represents an acid-labile protecting group, R3 represents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein R2, R3 and W are defined as above, each of R4, R5 and R6 independently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R4, R5 and R6 may be combined to form a ring. This polymer compound can provide a resist composition capable of forming a pattern that is transparent to exposure light and superior in rectangularity.
    Type: Grant
    Filed: June 11, 2008
    Date of Patent: February 15, 2011
    Assignee: Central Glass Company, Limited
    Inventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka
  • Patent number: 7887991
    Abstract: The present invention provides a polymer, having a high sensitivity, a high degree of resolution, a good pattern configuration after exposure, and in addition an excellent etching resistance, suitable as a base resin for a positive resist composition, especially for a chemically amplified positive resist composition; a positive resist composition using the polymer; and a patterning process. The positive resist composition of the present invention is characterized in that it contains at least, as a base resin, a polymer whose hydrogen atom of a phenolic hydroxide group is substituted by an acid labile group represented by the following general formula (1).
    Type: Grant
    Filed: January 22, 2009
    Date of Patent: February 15, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takanobu Takeda
  • Patent number: 7883828
    Abstract: Linear or branched functionalized polycarbosilanes having an absorbance less than 3.0 ?m?1 at 193 nm and a relatively high refractive index are provided. The functionalized polycarbosilanes contain at least one pendant group that is acid labile or aqueous base soluble. Also disclosed are photoresists formulations containing the functionalized polycarbosilanes that are suitable for use in lithography, e.g., immersion lithography.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: February 8, 2011
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 7867689
    Abstract: A method. The method includes dip coating a film of a composition on a silicon wafer substrate. The composition includes a polymer blend of a first polymer and a second polymer. The first polymer is a substituted silsesquioxane copolymer. The second polymer is a polysilsesquioxane having silanol end groups. The composition includes a photosensitive acid generator, an organic base, and an organic crosslinking agent. The film is patternwise imaged and at least one region is exposed to radiation having a wavelength of about 248 nanometers. The film is baked, resulting in inducing crosslinking in the film. The film is developed resulting in removal of base-soluble unexposed regions of the film, wherein a relief pattern from the film remains. The relief pattern is cured at a temperature between about 300° C. and about 450° C., and the curing utilizes a combination of thermal treatment with UV radiation.
    Type: Grant
    Filed: May 18, 2007
    Date of Patent: January 11, 2011
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Phillip Brock, Blake W. Davis, Qinghuang Lin, Robert D. Miller, Alshakim Nelson, Ratnam Sooriyakumaran
  • Patent number: 7867697
    Abstract: A positive photosensitive composition comprises: (A) 5 to 20 parts by weight of the total amount of at least one compound that generates an acid upon irradiation with an actinic ray; and (B) 100 parts by weight of the total amount of at least one fluorine atom-containing resin having a group that increases a solubility of the resin in an alkaline developer by the action of an acid.
    Type: Grant
    Filed: July 22, 2004
    Date of Patent: January 11, 2011
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7855045
    Abstract: A topcoat material for applying on top of a photoresist material is disclosed. The topcoat material comprises at least one solvent and a polymer which has a dissolution rate of at least 3000 ?/second in aqueous alkaline developer. The polymer contains a hexafluoroalcohol monomer unit comprising one of the following two structures: wherein n is an integer. The topcoat material may be used in lithography processes, wherein the topcoat material is applied on a photoresist layer. The topcoat material is preferably insoluble in water, and is therefore particularly useful in immersion lithography techniques using water as the imaging medium.
    Type: Grant
    Filed: October 5, 2007
    Date of Patent: December 21, 2010
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Phillip Joe Brock, Dario Gil, William Dinan Hinsberg, Carl Eric Larson, Linda Karin Sundberg, Gregory Michael Wallraff
  • Patent number: 7851140
    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: June 12, 2008
    Date of Patent: December 14, 2010
    Assignee: FUJIFILM Corporation
    Inventor: Hideaki Tsubaki
  • Patent number: 7838201
    Abstract: A polymer for immersion lithography comprising a repeating unit represented by Formula 1 and a photoresist composition containing the same. A photoresist film formed by the photoresist composition of the invention is highly resistant to dissolution, a photoacid generator in an aqueous solution for immersion lithography, thereby preventing contamination of an exposure lens and deformation of the photoresist pattern by exposure.
    Type: Grant
    Filed: April 8, 2009
    Date of Patent: November 23, 2010
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Cheol Kyu Bok, Chang Moon Lim, Seung Chan Moon
  • Patent number: 7833694
    Abstract: Lactone-containing compounds having formula (1) are novel wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are H or monovalent hydrocarbon groups, or R2 and R3 may together form an aliphatic hydrocarbon ring, R4 is H or CO2R5, R5 is a monovalent hydrocarbon group, W is CH2, O or S, and k1 is 3, 4 or 5. 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 properties including resolution, LER, pattern density dependency and exposure margin.
    Type: Grant
    Filed: March 12, 2009
    Date of Patent: November 16, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Satoshi Shinachi, Katsuhiro Kobayashi, Tsunehiro Nishi, Takeshi Kinsho
  • Patent number: 7824845
    Abstract: Linear or branched functionalized polycarbosilanes having an absorbance less than 3.0 ?m?1 at 193 nm and a relatively high refractive index are provided. The functionalized polycarbosilanes contain at least one pendant group that is acid labile or aqueous base soluble. Also disclosed are photoresists formulations containing the functionalized polycarbosilanes that are suitable for use in lithography, e.g., immersion lithography.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: November 2, 2010
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 7820369
    Abstract: Polymers containing an acetal or ketal linkage and their use in lithographic photoresist compositions, particularly in chemical amplification photoresists, are provided. The polymer is prepared from at least one first olefinic monomer containing an acetal or ketal linkage, the acid-catalyzed cleavage of which renders the polymer soluble in aqueous base; and at least one second olefinic monomer selected from (i) an olefinic monomer containing a pendant fluorinated hydroxyalkyl group RH, (ii) an olefinic monomer containing a pendant fluorinated alkylsulfonamide group RS, and (iii) combinations thereof. The acetal or ketal linkage may be contained within an acid-cleavable substituent RCL in the first olefinic monomer. A method for using the photoresist compositions containing these polymers in preparing a patterned substrate is also provided in which the polymer is rendered soluble in aqueous base at a temperature of less than about 100° C.
    Type: Grant
    Filed: December 4, 2003
    Date of Patent: October 26, 2010
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory Michael Wallraff
  • Patent number: 7811740
    Abstract: A positive resist composition comprising (A) resin having a monocyclic or polycyclic alicyclic hydrocarbon structure and capable of decomposing by the action of an acid to increase the solubility in an alkaline developer, (B) a compound capable of generating an acid upon treatment with one of an actinic ray and radiation and (F) a specific surfactant containing a fluorine atom in an amount of from 30 to 60 mass %, and a pattern-forming method using the same.
    Type: Grant
    Filed: October 7, 2005
    Date of Patent: October 12, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Hiromi Kanda, Fumiyuki Nishiyama
  • Patent number: 7803519
    Abstract: A method for manufacturing a semiconductor device using a photoresist polymer comprising a fluorine component, a photoresist composition containing the photoresist polymer and an organic solvent to reduce surface tension, by forming a photoresist film uniformly on the whole surface of an underlying layer pattern to allow a subsequent ion-implanting process to be stably performed.
    Type: Grant
    Filed: April 8, 2009
    Date of Patent: September 28, 2010
    Assignee: Hynix Semiconductor Inc.
    Inventor: Jae Chang Jung
  • Patent number: 7799507
    Abstract: A positive resist composition for immersion lithography of the present invention includes a resin component (A) which exhibits increased alkali solubility under the action of acid; and an acid generator component (B) which generates acid on exposure, wherein the resin component (A) includes a cyclic main chain resin (A1) containing a fluorine atom and no acid-dissociable group, and a resin (A2) containing a structural unit (a) derived from an acrylic acid and no fluorine atom.
    Type: Grant
    Filed: April 23, 2007
    Date of Patent: September 21, 2010
    Assignee: Tokyo Ohka Co., Ltd.
    Inventors: Kotaro Endo, Makiko Irie, Takeshi Iwai, Yoshiyuki Utsumi, Yasuhiro Yoshii, Tsuyoshi Nakamura