Patents Examined by Sin J. Lee
  • Patent number: 8933251
    Abstract: A fluorinated monomer of cyclic acetal structure has formula (1) wherein R is a C1-C20 alkyl group which may be substituted with halogen or separated by oxygen or carbonyl, and Z is a divalent organic group which forms a ring with alkylenoxy and contains a polymerizable unsaturated group. A polymer derived from the fluorinated monomer may be endowed with appropriate water repellency, water sliding property, lipophilicity, acid lability and hydrolyzability and is useful in formulating a protective coating composition and a resist composition.
    Type: Grant
    Filed: March 20, 2013
    Date of Patent: January 13, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Satoshi Shinachi, Takeshi Kinsho, Koji Hasegawa, Yuji Harada, Jun Hatakeyama, Kazunori Maeda, Tomohiro Kobayashi
  • Patent number: 8916327
    Abstract: There is provided an underlayer coating forming composition for lithography, and an underlayer coating having a high dry etching rate compared with photoresist, and causing no intermixing with the photoresist, which are used in lithography process of manufacture of semiconductor device. Concretely, it is an underlayer coating forming composition for lithography comprising a dextrin ester compound that at least 50% of hydroxy groups in dextrin is converted into ester groups, a crosslinking compound, and an organic solvent.
    Type: Grant
    Filed: October 29, 2004
    Date of Patent: December 23, 2014
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Satoshi Takei, Yasushi Sakaida, Tetsuya Shinjo
  • Patent number: 8911932
    Abstract: Disclosed are the deactivation mechanism and chemistry platforms that make high-silicon hardmask films photo-imageable like positive-tone photoresist for microphotolithography. The deactivation mechanism requires a catalyst to promote crosslinking reactions, and a photoacid generator to deactivate the catalyst. The initial hardmask films are soluble in developers. If not radiated, films become insoluble in developers due to crosslinking reactions promoted by catalyst. If radiated, films remain soluble in developers due to deactivation of catalyst by photoacid generator. Compositions of positive-tone photo-imageable hardmask based on the chemistry of polysiloxane and polysilsesquioxanes are disclosed as well. Also disclosed is a method of modifying polysiloxane and polysilsesquioxane films for controlled diffusion of catalysts, photoacid generators, and quenchers.
    Type: Grant
    Filed: April 12, 2010
    Date of Patent: December 16, 2014
    Inventor: Sam Xunyun Sun
  • Patent number: 8900794
    Abstract: A photoacid generator compound has the formula (I): [A-(CHR1)p]k-(L)-(CH2)m—(C(R2)2)n—SO3?Z+??(I) wherein A is a substituted or unsubstituted, monocyclic, polycyclic, or fused polycyclic C5 or greater cycloaliphatic group optionally comprising O, S, N, F, or a combination comprising at least one of the foregoing, R1 is H, a single bond, or a substituted or unsubstituted C1-30 alkyl group, wherein when R1 is a single bond, R1 is covalently bonded to a carbon atom of A, each R2 is independently H, F, or C1-4 fluoroalkyl, wherein at least one R2 is not hydrogen, L is a linking group comprising a sulfonate group, a sulfonamide group, or a C1-30 sulfonate or sulfonamide-containing group, Z is an organic or inorganic cation, p is an integer of 0 to 10,k is 1 or 2, m is an integer of 0 or greater, and n is an integer of 1 or greater.
    Type: Grant
    Filed: September 28, 2012
    Date of Patent: December 2, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, Shintaro Yamada, William Williams, III
  • Patent number: 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: 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: 8900796
    Abstract: The present invention provides an acid generator generates a sulfonic acid represented by the following general formula (1) in response to high-energy beam or heat: To provide a novel acid generator which is suitably used as an acid generator for a resist composition, which solves the problems of LER and a depth of focus and can be effectively and widely used particularly without degradation of a resolution, a chemically amplified resist composition using the same, and a patterning process.
    Type: Grant
    Filed: February 15, 2013
    Date of Patent: December 2, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Tomohiro Kobayashi, Masayoshi Sagehashi
  • Patent number: 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: 8889332
    Abstract: A polymerizable composition includes an organic modified silicate selected from the group consisting of silsesquioxanes having the composition RSiO1.5, partially condensed alkoxysilanes, organically modified silicates having the composition RSiO3 and R2SiO2, and partially condensed orthosilicates having the composition SiOR4, where R is an organic substituent; a decomposable organic compound; a photoinitiator; and a release agent. The composition polymerizes upon exposure to UV radiation to form an inorganic silica network, and the decomposable organic compound decomposes upon exposure to heat to form pores in the inorganic silica network. The composition may be used to form a patterned dielectric layer in an integrated circuit device. A metallic film may be disposed on the patterned dielectric layer and then planarized.
    Type: Grant
    Filed: June 29, 2011
    Date of Patent: November 18, 2014
    Assignees: Canon Nanotechnologies, Inc., Molecular Imprints, Inc.
    Inventors: Frank Y. Xu, Jun Sung Chun, Michael P. C. Watts
  • Patent number: 8883397
    Abstract: A positive photosensitive siloxane composition containing: a polysiloxane (Ia), which is obtained by hydrolyzing and condensing the silane compound represented by RSi(OR1)3 in general formula (1) and the silane compound represented by Si(OR1)4 in general formula (2) in the presence of a basic catalyst, and a pre-baked film of which has a dissolution rate of 1,000 ?/second or less in a 5 wt % TMAH aqueous solution; a polysiloxane (Ib), which is obtained by hydrolyzing and condensing at least the silane compound represented by general formula (1) in the presence of an acid or basic catalyst, and a pre-baked film of which has a dissolution rate of 100 ?/second or more in a 2.38 wt % TMAH aqueous solution; and a diazonaphthoquinone derivative and solvent.
    Type: Grant
    Filed: August 19, 2011
    Date of Patent: November 11, 2014
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Daishi Yokoyama, Takashi Fuke, Yuji Tashiro, Takashi Sekito, Toshiaki Nonaka
  • Patent number: 8877424
    Abstract: A polymer is prepared from an adamantane methacrylate monomer whose alcoholic hydroxyl group is protected with an alicyclic-containing tertiary alkyl group. A photoresist composition comprising the polymer displays a high sensitivity and a high dissolution contrast during both alkaline development and organic solvent development.
    Type: Grant
    Filed: February 8, 2013
    Date of Patent: November 4, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayoshi Sagehashi, Jun Hatakeyama, Koji Hasegawa, Kazuhiro Katayama
  • Patent number: 8877425
    Abstract: A resist underlayer film forming composition for lithography includes: as a component (I), a fluorine-containing highly branched polymer obtained by polymerizing a monomer A having two or more radical polymerizable double bonds in the molecule thereof, a monomer B having a fluoroalkyl group and at least one radical polymerizable double bond in the molecule thereof, and a monomer D having a silicon atom-containing organic group and at least one radical polymerizable double bond in the molecule thereof, in the presence of a polymerization initiator C in a content of 5% by mole or more and 200% by mole or less, based on the total mole of the monomer A, the monomer B, and the monomer D; and as a component (II), a hydrolyzable silane compound, a hydrolysis product thereof, a hydrolysis-condensation product thereof, or a silicon-containing compound that is a combination of these compounds.
    Type: Grant
    Filed: October 20, 2011
    Date of Patent: November 4, 2014
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Yuta Kanno, Makoto Nakajima, Tomoko Misaki, Motonobu Matsuyama, Masayuki Haraguchi
  • 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: 8859180
    Abstract: [Task to Be Achieved] To provide a chemically amplified type positive copolymer for semiconductor lithography, which has eliminated the problems of prior art, has a high development contrast, and has excellent resolution in fine-pattern formation; a composition for semiconductor lithography which contains the copolymer; and a process for producing the copolymer. [Means for Achievement] The copolymer for semiconductor lithography according to the present invention is a copolymer which has at least (A) a repeating unit having a structure which has an alkali-soluble group protected by an acid-labile, dissolution-suppressing group, (B) a repeating group having a lactone structure and (C) a repeating group having an alcoholic hydroxyl group and which is characterized by having an acid value of 0.01 mmol/g or less as determined by dissolving the copolymer in a solvent and subjecting the solution to neutralization titration with a solution of an alkali metal hydroxide using Bromothymol Blue as an indicator.
    Type: Grant
    Filed: October 19, 2007
    Date of Patent: October 14, 2014
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Tomo Oikawa, Takayoshi Okada, Masaaki Kudo, Takanori Yamagishi
  • Patent number: 8852848
    Abstract: The present invention relates to an aqueous composition for coating over a photoresist pattern comprising a first water soluble compound comprising at least a silicon moiety and at least one amino group, and a second compound comprising at least 1 carboxylic acid group. The invention further relates to processes for using the novel invention.
    Type: Grant
    Filed: July 28, 2010
    Date of Patent: October 7, 2014
    Assignee: Z Electronic Materials USA Corp.
    Inventors: Hengpeng Wu, Meng Li, Yi Cao, Jian Yin, DongKwan Lee, SungEun Hong, Margareta Paunescu
  • 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: 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: 8846292
    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 good shape and a method of forming a resist pattern and novel compositions 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. Radiation-sensitive composition containing a solvent and a cyclic compound having, e.g., a cyclic compound (A) having a molecular weight of 700 to 5000 which is synthesized by the condensation reaction of a compound having 2 to 59 carbon atoms and 1 to 4 formyl groups with a compound having 6 to 15 carbon atoms and 1 to 3 phenolic hydroxyl groups, and a cyclic compound for use in the radiation-sensitive composition.
    Type: Grant
    Filed: December 29, 2011
    Date of Patent: September 30, 2014
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masatoshi Echigo, Dai Oguro
  • Patent number: 8841059
    Abstract: A negative resist composition, which shows excellent sensitivity and resolution in pattern formation by exposure to electron beams or EUV, a novel crosslinking agent suitable for the resist composition, and a pattern forming method using the resist composition are presented. The negative resist composition comprises: (A) a polyphenol compound comprising two or more phenolic hydroxyl groups in a molecule thereof and having a molecular weight of 300 to 3,000, (B) an acid generator which directly or indirectly produces acid by exposure to active energy rays having a wavelength of 248 nm or less, and (C) a crosslinking agent represented by the chemical formula (1).
    Type: Grant
    Filed: September 29, 2009
    Date of Patent: September 23, 2014
    Assignee: Dai Nippon Printing Co., Ltd.
    Inventors: Kenichi Okuyama, Yasunori Nagatsuka