Nitrogen Compound Containing Patents (Class 430/919)

Cross-Reference Art Collections

Nitrogen in heterocyclic ring (Class 430/920)
  • Patent number: 9040220
    Abstract: A resist composition including a base component which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component which generates acid upon exposure, the acid-generator including an acid generator consisting of a compound represented by general formula (b1-1) shown below: In which RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Grant
    Filed: March 2, 2012
    Date of Patent: May 26, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9034556
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) including an acid generator (B1) consisting of a compound represented by general formula (b1-1) shown below: wherein RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Grant
    Filed: December 18, 2008
    Date of Patent: May 19, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9029070
    Abstract: There are provided a method of forming a resist pattern includes: a step (1) in which a resist composition containing a base component (A) that generates base upon exposure and exhibits increased solubility in an alkali developing solution by the action of acid is applied to a substrate to form a resist film; a step (2) in which the resist film 2 is subjected to exposure; a step (3) in which baking is conducted after the step (2); and a step (4) in which the resist film 2 is subjected to an alkali development, thereby forming a negative-tone resist pattern in which the unexposed portion 2b of the resist film 2 has been dissolved and removed, and the resist composition used in the step (1).
    Type: Grant
    Filed: November 2, 2012
    Date of Patent: May 12, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito
  • Patent number: 9023585
    Abstract: A resist composition which generates a base upon exposure and exhibits increased solubility in an alkali developing solution under the action of acid, and the resist composition including: a base component (A) that exhibits increased solubility in an alkali developing solution under the action of acid; an acidic compound component (G1) including a nitrogen-containing cation having a pKa value of 7 or less and a counteranion; and a buffer component (K) including a nitrogen-containing cation and a counteranion being a conjugate base for the acid having a pKa value of 0 to 5.
    Type: Grant
    Filed: June 20, 2013
    Date of Patent: May 5, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito, Hiroaki Shimizu
  • Patent number: 9012129
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) including a compound represented by (b1-1), a compound represented by (b1-1?) and/or a compound represented by (b1-1?) (R1?-R3? represents an aryl group or an alkyl group, provided that at least one of R1?-R3? represents a substituted aryl group being substituted with a group represented by (b1-1-0), and two of R1?-R3? may be mutually bonded to form a ring with the sulfur atom; X represents a C3-C30 hydrocarbon group; Q1 represents a carbonyl group-containing divalent linking group; X10 represents a C1-C30 hydrocarbon group; Q3 represents a single bond or a divalent linking group; Y10 represents —C(?O)— or —SO2—; Y11 represents a C1-C10 alkyl group or a fluorinated alkyl group: Q2 represents a single bond or an alkylene group; and W represents a C2-C10 alkylene group).
    Type: Grant
    Filed: January 6, 2014
    Date of Patent: April 21, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
  • Patent number: 9005872
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in a developing solution under action of acid, a basic-compound component (C) and an acid-generator component (B) which generates acid upon exposure, the component (B) including a compound represented by formula (b1), and the component (C) including at least one compound represented by formulas (c1) to (c3) (wherein Z1 represents a ring skeleton-containing hydrocarbon group, Q1 represents a divalent linking group containing oxygen, Y1 represents a fluorinated alkylene group, M+ represents an organic cation, R1 represents a fluorinated alkyl group or a hydrocarbon group, L1+ and L2+ represents a sulfonium or an iodonium, Z2 represents a hydrogen atom or a hydrocarbon group, Y2 represents a single bond or a divalent linking group containing no fluorine, R2 represents an organic group, Y3 represents an alkylene group or an arylene group; and Rf represents a fluorine-containing hydrocarbon group).
    Type: Grant
    Filed: February 16, 2012
    Date of Patent: April 14, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Sho Abe, Hideto Nito
  • Patent number: 8980527
    Abstract: A resist composition is provided comprising a polymer comprising recurring units having a carboxyl group substituted with an acid labile group, an acid generator, a sulfonium or iodonium salt of fluoroalkanesulfonamide and an organic solvent. A positive pattern is formed by applying the resist composition onto a substrate, prebaking to form a resist film, exposing the resist film to high-energy radiation, baking, and immersing in an alkaline developer to dissolve away the exposed region of resist film, but not the unexposed region.
    Type: Grant
    Filed: January 4, 2013
    Date of Patent: March 17, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Jun Hatakeyama
  • Patent number: 8962233
    Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes an arylsulfonium salt that when exposed to actinic rays or radiation, generates an acid, the arylsulfonium salt containing at least one aryl ring on which there are a total of one or more electron donating groups, the acid generated upon exposure to actinic rays or radiation having a volume of 240 ?3 or greater.
    Type: Grant
    Filed: January 28, 2011
    Date of Patent: February 24, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Takeshi Kawabata, Tomotaka Tsuchimura, Takayuki Ito
  • Patent number: 8956806
    Abstract: A method and material layer for forming a pattern are disclosed. The method includes providing a substrate; forming a first material layer over the substrate; forming a second material layer over the first material layer, wherein the second material layer comprises a photoacid generator and a photobase generator; and exposing one or more portions of the second material layer.
    Type: Grant
    Filed: September 18, 2009
    Date of Patent: February 17, 2015
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Chien-Wei Wang, Ching-Yu Chang, Burn Jeng Lin
  • Patent number: 8956799
    Abstract: A photoacid generator includes those of formula (I): wherein each Ra in formula 1 is independently H, F, a C1-10 nonfluorinated organic group, C1-10 fluorinated organic group, or a combination comprising at least one of the foregoing, provided at least one Ra is F or a C1-10 fluorinated organic group, the C1-10 fluorinated and nonfluorinated organic groups each optionally comprising O, S, N, or a combination comprising at least one of the foregoing heteroatoms; L1 is a linking group comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing; G+ is an onium salt of the formula (II): wherein in formula (II), X is S or I, each R0 is independently C1-30 alkyl group; a polycyclic or monocyclic C3-30 cycloalkyl group; a polycyclic or monocyclic C4-30 aryl group; or a combination comprising at least one of the foregoing, provided at least one R0 is substituted where each R0 is a C6 monocyclic aryl group, and wherein when X is I, a is 2, and where X is S, a is 3,
    Type: Grant
    Filed: December 12, 2012
    Date of Patent: February 17, 2015
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, William Williams, III
  • Patent number: 8940471
    Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes a compound that when exposed to actinic rays or radiation, generates any of acids of general formula (I) below, in which W1 represents an optionally substituted alkylene group, W2 represents a bivalent connecting group, W3 represents an optionally substituted organic group having 15 or more carbon atoms, and Z represents a hydroxyl group or a fluoroalkylsulfonamido group having at least one fluorine atom introduced therein as a substituent.
    Type: Grant
    Filed: September 30, 2010
    Date of Patent: January 27, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Takeshi Kawabata, Tomotaka Tsuchimura, Takayuki Ito
  • Patent number: 8921027
    Abstract: A radiation-sensitive resin composition includes an acid-labile group-containing resin, and a compound shown by the following general formula (i). R1 represents a hydrogen atom or the like, R2 represents a single bond or the like, R3 represents a linear or branched unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms or the like, and X+ represents an onium cation.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: December 30, 2014
    Assignee: JSR Corporation
    Inventors: Ryuichi Serizawa, Nobuji Matsumura, Hirokazu Sakakibara
  • Patent number: 8921031
    Abstract: Provided are photoresist overcoat compositions, substrates coated with the overcoat compositions and methods of forming electronic devices by a negative tone development process. The compositions, coated substrates and methods find particular applicability in the manufacture of semiconductor devices.
    Type: Grant
    Filed: September 9, 2012
    Date of Patent: December 30, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Young Cheol Bae, Rosemary Bell, Jong Keun Park, Seung-Hyun Lee
  • 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: 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: 8895231
    Abstract: A pattern is formed by coating a first positive resist composition comprising a base resin, a photoacid generator, and a base generator having both a 9-fluorenylmethyloxycarbonyl-substituted amino group and a carboxyl group 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 an alcohol and an optional 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: September 2, 2011
    Date of Patent: November 25, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Kazuhiro Katayama
  • Patent number: 8846296
    Abstract: A composition is provided. The composition includes a polymer and a photosensitive acid generator capable of generating a first amount of acid upon exposure to a first dose of radiation and a second amount of acid upon exposure to a second dose of radiation. The second amount of acid is greater than the first amount of acid. The second dose is greater than the first dose. The composition includes a photosensitive base generator capable of generating a first amount of base upon exposure to the first dose and a second amount of base upon exposure to the second dose, where the first amount of base is greater than the first amount of acid and the second amount of base is less than the second amount of acid. The photosensitive base generator may include benzoin carbamates, O-carbamoylhydroxylamines, O-carbamoyloximes, aromatic sulfonamides, ?-lactones, N-(2-Arylethenyl)amides, azides, amides, oximines, quaternary ammonium salts, or amineimides.
    Type: Grant
    Filed: May 2, 2012
    Date of Patent: September 30, 2014
    Assignee: International Business Machines Corporation
    Inventors: Kuang-Jung Chen, Wu-Song Huang, Ranee Wai-Ling Kwong, Sen Liu, Pushkara R. Varanasi
  • Patent number: 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: 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: 8778596
    Abstract: A photosensitive resin composition which is excellent in resolution, low in cost, and usable in a wide range of structures of polymer precursors each of which is reacted into a final product by a basic substance or by heating in the presence of a basic substance. The photosensitive resin composition includes a base generator which has a specific structure and generates a base by exposure to electromagnetic radiation and heating, and a polymer precursor which is reacted into a final product by the base generator and by a basic substance or by heating in the presence of a basic substance.
    Type: Grant
    Filed: April 25, 2013
    Date of Patent: July 15, 2014
    Assignee: Dai Nippon Printing Co., Ltd.
    Inventors: Mami Katayama, Shunji Fukuda, Katsuya Sakayori
  • Patent number: 8722311
    Abstract: There is provided a resist composition suitable for forming a microlens which is excellent in transparency, heat resistance, and sensitivity characteristics, excellent in solubility in a developer, and as the result thereof has high resolution. A positive resist composition comprising; a component (A): an alkali-soluble polymer; a component (B): a compound having an organic group to be photolyzed to generate an alkali-soluble group; a component (C): a crosslinkable compound of Formula (1): [where R1, R2, and, R3 are independently a C1-6 alkylene group or oxyalkylene group which are optionally branched; and E1, E2, and E3 are independently a group containing a structure of Formula (2) or Formula (3): (where R4 is a hydrogen atom or a methyl group)]; and a component (D): a solvent.
    Type: Grant
    Filed: January 19, 2011
    Date of Patent: May 13, 2014
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Shojiro Yukawa, Shinya Arase, Toshiaki Takeyama, Yuki Endo, Takeo Moro
  • Patent number: 8703384
    Abstract: A positive resist composition comprising (A) a polymer comprising recurring units of a specific structure adapted to generate an acid in response to high-energy radiation and acid labile units, the polymer having an alkali solubility that increases under the action of an acid, and (B) a sulfonium salt of a specific structure exhibits a high resolution in forming fine size patterns, typically trench patterns and hole patterns. Lithographic properties of profile, DOF and roughness are improved.
    Type: Grant
    Filed: November 23, 2011
    Date of Patent: April 22, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Kobayashi, Eiji Fukuda, Takayuki Nagasawa, Ryosuke Taniguchi, Youichi Ohsawa, Masayoshi Sagehashi, Yoshio Kawai
  • Patent number: 8697332
    Abstract: An object of the present invention is to provide a base generator which has sensitivity and is applicable to a wide range of applications, and a photosensitive resin composition which is applicable to a wide range of applications due to the structure of a polymer precursor in which reaction into a final product is promoted by a basic substance or by heating in the presence of a basic substance. The base generator generates a base by exposure to electromagnetic radiation and heating. The photosensitive resin composition comprises a polymer precursor in which reaction into a final product is promoted by the base generator and a basic substance or by heating in the presence of a basic substance.
    Type: Grant
    Filed: March 26, 2010
    Date of Patent: April 15, 2014
    Assignee: Dai Nippon Printing Co., Ltd.
    Inventors: Mami Katayama, Shunji Fukuda, Katsuya Sakayori, Kouji Kawaguchi
  • Patent number: 8691352
    Abstract: Disclosed is a photopolymerizable composition which contains a photopolymerization initiator (A) that has a partial structure represented by the following Formula (1) and a polymerizable compound (B). In General formula (1), R3 and R4 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group or an alkoxy group; R3 and R4 may form a ring with each other; and X represents OR5, SR6, or NR17R18. The photopolymerizable composition is capable of forming a cured film that has high sensitivity, excellent intra-membrane curability and excellent adhesion to a support. The cured film is able to maintain a patterned shape even during post-heating after development and has good pattern formability, while coloring due to heating with passage of time being suppressed.
    Type: Grant
    Filed: August 10, 2010
    Date of Patent: April 8, 2014
    Assignee: FUJIFILM Corporation
    Inventor: Masaomi Makino
  • Patent number: 8685616
    Abstract: The present invention provides photoacid generators for use in chemically amplified resists and lithographic processes using the same.
    Type: Grant
    Filed: June 10, 2009
    Date of Patent: April 1, 2014
    Assignee: University Of North Carolina At Charlotte
    Inventors: Kenneth E. Gonsalves, Mingxing Wang
  • Patent number: 8658344
    Abstract: A resist material and methods using the resist material are disclosed herein. An exemplary method includes forming a resist layer over a substrate, wherein the resist layer includes a polymer, a photoacid generator, an electron acceptor, and a photodegradable base; performing an exposure process that exposes portions of the resist layer with radiation, wherein the photodegradable base is depleted in the exposed portions of the resist layer during the exposure process; and performing an developing process on the resist layer.
    Type: Grant
    Filed: June 27, 2012
    Date of Patent: February 25, 2014
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Chien-Wei Wang, Ching-Yu Chang, Tsai-Sheng Gau, Burn Jeng Lin
  • 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: 8642245
    Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes a resin that is decomposed when acted on by an acid to thereby increase its solubility in an alkali developer, a compound that generates an acid when exposed to actinic rays or radiation, and any of basic compounds of general formula (1) below.
    Type: Grant
    Filed: March 15, 2012
    Date of Patent: February 4, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Kana Fujii, Tomotaka Tsuchimura, Toru Fujimori, Hidenori Takahashi, Takayuki Ito
  • Patent number: 8617786
    Abstract: The present invention relates to compositions comprising poly-oxycarbosilane and methods for using the compositions in step and flash imprint lithography. The imprinting compositions comprise a poly-oxycarbosilane polymer, a silanol, a reaction initiator and optionally a pore generator.
    Type: Grant
    Filed: February 11, 2011
    Date of Patent: December 31, 2013
    Assignee: International Business Machines Corporation
    Inventors: Richard Anthony Dipietro, Geraud Jean-Michel Dubois, Robert Dennis Miller, Ratnam Sooriyakumaran
  • Patent number: 8563222
    Abstract: A lithographic printing plate precursor comprising an image-recording layer, said image-recording layer being photopolymerizable upon exposure to light having a wavelength of from 300 to 500 nm and containing a mixture of sensitizers.
    Type: Grant
    Filed: May 15, 2008
    Date of Patent: October 22, 2013
    Assignee: Agfa Graphics NV
    Inventors: Jan Venneman, Peter Hendrikx, Paul Callant, Alexander Williamson
  • Patent number: 8546061
    Abstract: A photo-curing polysiloxane composition includes a polysiloxane, an o-naphthoquinonediazidesulfonate compound, and a solvent. The polysiloxane contains 25 wt % to 60 wt % of a polysiloxane fraction having a molecular weight ranging from 10,000 to 80,000 based on a total weight of the polysiloxane when calculated from an integral molecular weight distribution curve obtained by plotting cumulative weight percentage versus molecular weight falling within a range between 400 and 100,000 measured by gel permeation chromatography. The amount of oligomers in the polysiloxane having a molecular weight less than 800 is from 0 wt % to 10 wt % based on a total weight of the photo-curing polysiloxane composition. A protective film formed from the photo-curing polysiloxane composition and an element containing the protective film are also disclosed.
    Type: Grant
    Filed: November 8, 2011
    Date of Patent: October 1, 2013
    Assignee: Chi Mei Corporation
    Inventors: Ming-Ju Wu, Chun-An Shih
  • Patent number: 8541157
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under the action of acid and an acid-generator component (B) which generates acid upon exposure, wherein the acid-generator component (B) includes an acid generator (B1) composed of a compound having a base dissociable group within a cation moiety.
    Type: Grant
    Filed: September 25, 2009
    Date of Patent: September 24, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Sho Abe
  • Patent number: 8530137
    Abstract: The present invention provides a photoresist composition having a sulfonium salt comprising an anion represented by the formula (IA): wherein R1 and R2 independently represent a hydrogen atom, a C1-C12 aliphatic hydrocarbon group, a C3-C20 saturated cyclic hydrocarbon group, a C6-C20 aromatic hydrocarbon group or a C7-C21 aralkyl group, and the aliphatic hydrocarbon group, the saturated cyclic hydrocarbon group, the aromatic hydrocarbon group and the aralkyl group can have one or more substituents selected from the group consisting of a hydroxyl group, a cyano group, a fluorine atom, a trifluoromethyl group and a nitro group, and one or more —CH2— in the aliphatic hydrocarbon group can be replaced by —O— or —CO—, or R1 and R2 are bonded each other to form a C4-C20 nitrogen-containing ring together with the nitrogen atom to which they are bonded, an acrylic resin having an acid-labile group and being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solutio
    Type: Grant
    Filed: February 11, 2011
    Date of Patent: September 10, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Satoshi Yamaguchi
  • Patent number: 8507175
    Abstract: The process forms a pattern by applying a resist composition onto a substrate to form a resist film, baking, exposure, post-exposure baking, and development. The resist composition comprises a polymer comprising recurring units having an acid labile group and substantially insoluble in alkaline developer, a PAG, a PBG capable of generating an amino group, a quencher for neutralizing the acid from PAG for inactivation, and an organic solvent. A total amount of amino groups from the quencher and PBG is greater than an amount of acid from PAG. An unexposed region and an over-exposed region are not dissolved in developer whereas only an intermediate exposure dose region is dissolved in developer. Resolution is doubled by splitting a single line into two through single exposure and development.
    Type: Grant
    Filed: October 15, 2010
    Date of Patent: August 13, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Masaki Ohashi, Youichi Ohsawa, Kazuhiro Katayama
  • Patent number: 8501382
    Abstract: There are disclosed sulfonic acid precursor compositions, as are methods of using these compositions in, for example, photolithography. Other embodiments are also disclosed.
    Type: Grant
    Filed: February 19, 2010
    Date of Patent: August 6, 2013
    Assignee: The Research Foundation of State Univ. of New York
    Inventor: Robert L. Brainard
  • Patent number: 8450041
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes (A) a compound capable of generating a specific acid having a norbornyl structure upon irradiation with an actinic ray or radiation, and (B) a resin capable of increasing the dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure on the resin side chain through a linking group, and a pattern forming method uses the composition.
    Type: Grant
    Filed: January 15, 2010
    Date of Patent: May 28, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Shuhei Yamaguchi
  • Patent number: 8435717
    Abstract: A sulfonic acid onium salt represented by the following formula (1) can be used as a superior radiosensitive acid generator for resist compositions. It is possible to form a good pattern by using a resist composition containing this sulfonic acid onium salt. In formula (1), R1 represents a monovalent organic group, and Q+ represents a sulfonium cation or iodonium cation.
    Type: Grant
    Filed: February 14, 2008
    Date of Patent: May 7, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
  • Patent number: 8431323
    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: October 29, 2009
    Date of Patent: April 30, 2013
    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: 8426113
    Abstract: The present invention provides chemically amplified silsesquioxane polymers for preparing masks using e-beam lithography. The silsesquioxane polymers have reactive sidechains that in the presence of an acid undergo acid catalyzed rearrangement to generate reactive functionalities that crosslink to form Si—O—Si bonds. The reactive side-chains comprise ?- and ?-substituted alkyl groups bound to the silicon of the silsesquioxane polymer. The substituent of the ?- and ?-substituted alkyl group is an electron withdrawing group. Resists generated with the chemically amplified silsesquioxane polymers of the present invention and imaged with e-beams have resolution of ?60 nm line/space.
    Type: Grant
    Filed: August 13, 2010
    Date of Patent: April 23, 2013
    Assignee: International Business Machines Corporation
    Inventors: Luisa Dominica Bozano, Blake W. Davis, Alshakim Nelson, Jitendra Singh Rathore, Linda Karin Sundberg
  • Patent number: 8415081
    Abstract: The present invention discloses a photosensitive resin composition which comprises (A) a compound having a molecule with at least one thiirane ring and a total number of a thiirane ring and/or an epoxy ring of at least 2 in the molecule, and (B) a photo acid generator, said composition having a refractive index of at least 1.6, and a method of obtaining a high refractive index periodical structure which comprises subjecting the photosensitive resin composition to photolithography.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: April 9, 2013
    Assignees: Cornell Research Foundation, Inc., Hitachi Chemical Co., Ltd.
    Inventors: Christopher K. Ober, Yasuharu Murakami
  • Patent number: 8377627
    Abstract: A compound shown by the following formula (1).
    Type: Grant
    Filed: July 30, 2008
    Date of Patent: February 19, 2013
    Assignee: JSR Corporation
    Inventors: Daisuke Shimizu, Ken Maruyama, Toshiyuki Kai, Tsutomu Shimokawa
  • Patent number: 8349533
    Abstract: A resist lower-layer composition configured to be used by a multi-layer resist method used in lithography to form a layer lower than a photoresist layer acting as a resist upper layer film. The resist lower-layer composition is insoluble or poorly-soluble in an alkaline developer after formation of the lower layer, and the resist lower-layer composition comprises, at least, a thermal acid generator for generating an acid by heating at a temperature of 100° C. or higher.
    Type: Grant
    Filed: October 20, 2009
    Date of Patent: January 8, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Jun Hatakeyama, Takeru Watanabe, Takeshi Kinsho
  • Patent number: 8334088
    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: November 3, 2010
    Date of Patent: December 18, 2012
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 8304164
    Abstract: The present invention provides a photoresist composition comprising: at least one selected from the group consisting of a monomer represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, W1 represents a C3-C20 divalent saturated cyclic hydrocarbon group, A1 represents a single bond or *-O—CO—W1— wherein * represents a binding position to W1?N— and W1 represents a C1-C10 divalent saturated hydrocarbon group, a polymer consisting of a structural unit derived from the monomer represented by the formula (I) and a polymer consisting of a structural unit derived from the monomer represented by the formula (I) and a structural unit derived from a monomer represented by the formula (II): wherein R3 represents a hydrogen atom or a methyl group, A2 represents a single bond or *-O—CO—(CH2)n— wherein * represents a binding position to R4—, n represents an integer of 1 to 7 and R4 represents a C3-C20 saturated cyclic hydrocarbon group, a resin having an acid-labile group
    Type: Grant
    Filed: January 3, 2011
    Date of Patent: November 6, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Yuichi Mukai, Masahiko Shimada
  • Patent number: 8273521
    Abstract: A radiation-sensitive resin composition includes a compound shown by a formula (1) in which R1 represents a divalent hydrocarbon group having 1 to 20 carbon atoms and R2 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, or R1 and R2 form a heterocyclic structure having 4 to 20 carbon atoms, R3 represents a monovalent acid-dissociable group, n is an integer from 1 to 6, each of R4A, R4B, and R4C represents one of an alkyl group having 1 to 4 carbon atoms and a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms, or R4A represents one of an alkyl group having 1 to 4 carbon atoms and a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms and R4B and R4C form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms.
    Type: Grant
    Filed: July 30, 2010
    Date of Patent: September 25, 2012
    Assignee: JSR Corporation
    Inventors: Mitsuo Sato, Kazuo Nakahara, Hiromitsu Nakashima, Takanori Nakano, Makoto Sugiura
  • Patent number: 8252507
    Abstract: A novel photoactive compound is provided. The photoactive compound has a structure represented by Formula 1: wherein R1, R2, R3, A, X, Y, n and m are as defined in the specification. The photoactive compound efficiently absorbs UV light. Accordingly, the photoactive compound has an improved ability to generate radicals and is efficiently photopolymerized with unsaturated bonds. Further provided is a photosensitive resin composition comprising the photoactive compound. The photosensitive resin composition has good sensitivity because it efficiently absorbs UV light. In addition, the photosensitive resin composition has excellent characteristics in terms of residual film ratio, mechanical strength and resistance to heat, chemicals and development. Therefore, the photosensitive resin composition is advantageously used in curing materials for column spacers, overcoats and passivation films of liquid crystal display devices.
    Type: Grant
    Filed: April 1, 2009
    Date of Patent: August 28, 2012
    Assignee: LG Chem, Ltd.
    Inventors: Chang Ho Cho, Sung Hyun Kim, Raisa Kharbash, Keon Woo Lee, Sang Kyu Kwak, Dong Kung Oh, Chang Soon Lee, Kyoung Hoon Min
  • Patent number: 8236476
    Abstract: A method and a composition are provided. The composition includes a polymer and a photosensitive acid generator capable of generating a first amount of acid upon exposure to a first dose of radiation and a second amount of acid upon exposure to a second dose of radiation. The second amount of acid is greater than said first amount of acid. The second dose is greater than the first dose. The composition includes a photosensitive base generator capable of generating a first amount of base upon exposure to the first dose and a second amount of base upon exposure to the second dose, where the first amount of base is greater than the first amount of acid and the second amount of base is less than the second amount of acid. A method for exposing to radiation a film of a photoresist on a substrate is included.
    Type: Grant
    Filed: January 8, 2008
    Date of Patent: August 7, 2012
    Assignee: International Business Machines Corporation
    Inventors: Kuang-Jung Chen, Wu-Song Huang, Ranee Wai-Ling Kwong, Sen Liu, Pushkara R. Varanasi
  • Patent number: 8216767
    Abstract: A method for fabricating an integrated circuit device is disclosed. The method includes providing a substrate; forming a first material layer over the substrate; forming a second material layer over the first material layer, wherein the second material layer comprises a photodegradable base material; and exposing at least a portion of the second material layer.
    Type: Grant
    Filed: September 8, 2009
    Date of Patent: July 10, 2012
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Chien-Wei Wang, Ching-Yu Chang, Tsai-Sheng Gau, Burn Jeng Lin
  • Patent number: 8211619
    Abstract: The present invention provides: a positive photosensitive composition that yields an insulation layer superior not only in high transparency, but also in heat resistance enduring a temperature during the production of a substrate, solvent resistance, and anti-aging property as a permanent resist; a positive permanent resist utilizing the positive photosensitive composition; and a method for producing the positive permanent resist. The present invention provides: a positive photosensitive composition containing (A) a curable silicone resin having a silanol group, which resin has a structure obtained by a reaction between one or more cyclic siloxane compounds represented by the following general formula (1): and one or more arylalkoxysilane compounds represented by the following general formula (2): (B) diazonaphthoquinones, and (C) a solvent; a positive permanent resist using the positive photosensitive composition; and a method for producing the positive permanent resist.
    Type: Grant
    Filed: November 12, 2008
    Date of Patent: July 3, 2012
    Assignee: Adeka Corporation
    Inventors: Hiroshi Morita, Hiromi Sato, Atsushi Kobayashi, Jinichi Omi, Seiichi Saito
  • Patent number: 8206890
    Abstract: A resist composition including: a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid; and an acid-generator component (B) which generates acid upon exposure, wherein said acid-generator component (B) comprises an acid generator (B1) including a compound represented by general formula (b1-11) shown below: wherein R7? to R9? each independently represent an aryl group or an alkyl group, wherein two of R7? to R9? may be bonded to each other to form a ring with the sulfur atom, and at least one of R7? to R9? represents a substituted aryl group having a group represented by general formula (I) shown below as a substituent; X? represents an anion; and Rf represents a fluorinated alkyl group.
    Type: Grant
    Filed: July 8, 2009
    Date of Patent: June 26, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehiro Seshimo, Tsuyoshi Nakamura, Naoto Motoike, Hiroaki Shimizu, Kensuke Matsuzawa, Hideo Hada