Sulfur Compound Containing Patents (Class 430/921)

Cross-Reference Art Collections

Sulfur in heterocyclic ring (Class 430/922)
  • Patent number: 8318404
    Abstract: A salt represented by the formula (a1): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C4 perfluoroalkyl group, X1 represents —CO—O—Xa1— or —CH2—O—Xa2— wherein Xa1 and Xa2 independently each represent a C1-C15 alkylene group and one or more —CH2— in the alkylene group can be replaced by —O— or —CO—, Y1 represents a C3-C36 alicyclic hydrocarbon group or a C6-C24 aromatic hydrocarbon group, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O— or —CO—, and Z+ represents an organic cation.
    Type: Grant
    Filed: June 9, 2010
    Date of Patent: November 27, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Hiromu Sakamoto
  • 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: 8298746
    Abstract: The present invention provides a chemically amplified resist composition comprising: a resin (A) which itself is insoluble or poorly soluble in an aqueous alkali solution but becomes soluble in an aqueous alkali solution by the action of an acid and which comprises a structural unit having an acid-labile group in a side chain and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X1 represents an unsubstituted or substituted C3-C30 cyclic hydrocarbon group having —COO— and k represents an integer of 1 to 4, a resin (B) which comprises a structural unit represented by the formula (II): wherein R2 represents a hydrogen atom, a methyl group or a trifluoromethyl group, and an acid generator.
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: October 30, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junji Shigematsu, Kunishige Edamatsu, Takayuki Miyagawa, Akira Kamabuchi
  • Patent number: 8298748
    Abstract: A positive resist composition including a base component (A?) which exhibits increased solubility in an alkali developing solution under action of acid and generates acid upon exposure, the base component (A?) including a polymeric compound (A1?) having a structural unit (a5-1) represented by general formula (a5-1), a structural unit (a0-1) represented by general formula (a0-1) and a structural unit (a0-2) that generates acid upon exposure, the structural unit (a0-2) containing a group represented by general formula (a0-2?) (wherein X? represents an anion moiety represented by one of general formulas (1) to (5)).
    Type: Grant
    Filed: May 17, 2010
    Date of Patent: October 30, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Yoshitaka Komuro, Takeyoshi Mimura, Daichi Takaki
  • Patent number: 8293123
    Abstract: A method of manufacturing an inkjet printhead, in which a solvent included in a positive photoresist composition or in a non-photosensitive soluble polymer composition which is used to form a sacrificial layer has a different polarity from that of a solvent included in a negative photoresist composition that is used to form at least one of a channel forming layer and a nozzle layer.
    Type: Grant
    Filed: June 24, 2008
    Date of Patent: October 23, 2012
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Jong-jin Park, Su-min Kim, Jin-baek Kim, Yong-ung Ha, Yong-seop Yoon, Byung-ha Park
  • Patent number: 8288077
    Abstract: The object of the present invention is to provide a chemically amplified resist composition excellent in a resolution and a mask error enhancement factor. By employing the salt represented by the formulae (A1) as an acid generator of a resist composition, the above mentioned object is achieved. wherein Z+ represents an organic cation, Q1 and Q2 each independently represent a fluorine atom or a perfluoroalkyl group, Ra2 represents a divalent alicyclic hydrocarbon group pr the like, Ra2 represents an elimination group represented by the formulae (II-1) or (II-2). In the formulae (II-1) or (II-2), Ra3 and Ra4 each independently represent a hydrogen atom or an aliphatic hydrocarbon group, Ra5 represents an aliphatic hydrocarbon group, Ra6 represents a divalent aliphatic hydrocarbon group, and Ra7 represents an aliphatic hydrocarbon group.
    Type: Grant
    Filed: July 27, 2010
    Date of Patent: October 16, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Isao Yoshida, Satoshi Yamaguchi
  • Patent number: 8288078
    Abstract: A photosensitive resin composition is provided that is highly safe, provides a coating film having superior uniformity, can improve the curing density of the cured resin pattern, and is capable of forming a micro resist pattern having a large film thickness and a high aspect ratio with high sensitivity and high resolving ability. According to a photosensitive resin composition including, in addition to an onium fluorinated alkyl fluorophosphate based cation polymerization initiator having a specific structure, a specified solvent or a specified sensitizing agent as essential components, a coating film having superior uniformity, can improve the curing density of the cured resin pattern, and also is capable of forming a micro resist pattern having a large film thickness and a high aspect ratio with high sensitivity and high resolving ability.
    Type: Grant
    Filed: January 11, 2008
    Date of Patent: October 16, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takahiro Senzaki, Koichi Misumi, Atsushi Yamanouchi, Koji Saito
  • Patent number: 8288076
    Abstract: A chemically amplified resist composition comprises a polymer comprising units having polarity to impart adhesion and acid labile units adapted to turn alkali soluble under the action of acid. The polymer comprises recurring units having formula (1) wherein R1 is H, F, CH3 or CF3, Rf is H, F, CF3 or CF2CF3, A is a divalent hydrocarbon group, R2, R3 and R4 are alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl. Recurring units containing an aromatic ring structure are present in an amount ?60 mol % and the recurring units having formula (1) are present in an amount <5 mol %.
    Type: Grant
    Filed: May 28, 2010
    Date of Patent: October 16, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Keiichi Masunaga, Satoshi Watanabe, Akinobu Tanaka, Daisuke Domon
  • Patent number: 8283106
    Abstract: Disclosed is a fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound having a structure represented by the following general formula (A). In the formula, n indicates an integer of 1 to 10; R indicates a substituted or unsubstituted C1-C20 linear, branched or cyclic alkyl group, a substituted or unsubstituted C1-C20 linear, branched or cyclic alkenyl group, a substituted or unsubstituted C6-C15 aryl group, or a C4-C15 heteroaryl group; and a indicates 1 or 0. A photoacid generator containing the above fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound shows high sensitivity to an ArF excimer laser or the like, presents no concerns about human body accumulation, can generate an acid (photoacid) of sufficiently high acidity, and exhibits high solubility in a resist solvent and good compatibility with a resist resin.
    Type: Grant
    Filed: October 31, 2008
    Date of Patent: October 9, 2012
    Assignee: Central Glass Company, Limited
    Inventors: Kazuhiko Maeda, Yoshimi Isono, Satoru Narizuka
  • Patent number: 8283105
    Abstract: A positive resist composition including a base component (A) which exhibits increased solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the component (A) including a polymeric compound (A1) having an acid dissociable, dissolution inhibiting group in the structure thereof and including a structural unit (a0) having an —SO2— containing cyclic group on the terminal of the side chain, and the component (B) including an acid generator (B1) containing a compound represented by general formula (b1-1) (R0 represents a hydrocarbon group of 1 to 12 carbon atoms which may have a substituent, provided that the carbon atom adjacent to the sulfur atom within the —SO3? group has no fluorine atom bonded thereto, and Z+ represents an organic cation).
    Type: Grant
    Filed: March 4, 2010
    Date of Patent: October 9, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yasuhiko Kakinoya, Naoto Motoike
  • Patent number: 8283102
    Abstract: Disclosed are a photoacid generator, a copolymer, a chemically amplified resist composition, and a method of forming a pattern using the chemically amplified resist composition. The photoacid is connected with a main chain of the copolymer, whereby the photoacid is equally dispersed within a resist layer, and characteristics of line edge roughness of a resist pattern is improved.
    Type: Grant
    Filed: April 2, 2009
    Date of Patent: October 9, 2012
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung Hoon Oh, Sang Jin Kim, Jin Ho Kim, Dae Hyeon Shin
  • Patent number: 8278023
    Abstract: A salt represented by the formula (I-BB): wherein Q1 and Q2 each independently represent a fluorine atom etc., X1 represents a single bond etc., Y1 represents a C1-C36 aliphatic hydrocarbon group etc., A1 and A2 independently each represents a C1-C20 aliphatic hydrocarbon group etc., Ar1 represents a (m4+1)-valent C6-C20 aromatic hydrocarbon group which can have one or more substituents, B1 represents a single bond etc., B2 represents a C4-C36 alicyclic hydrocarbon group which has one or more —OXa groups and which is not capable of being eliminated by the action of an acid etc., and Xa represents a hydrogen atom or a group capable of being eliminated by the action of an acid, m1 and m2 independently each represents an integer of 0 to 2, m3 represents an integer of 1 to 3, with the proviso that m1 plus m2 plus m3 equals 3, and m4 represents an integer of 1 to 3.
    Type: Grant
    Filed: May 25, 2010
    Date of Patent: October 2, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Tatsuro Masuyama
  • Patent number: 8252518
    Abstract: There is disclosed a chemically amplified positive resist composition to form a chemically amplified resist film to be used in a lithography, wherein the chemically amplified positive resist composition comprises at least, (A) a base resin, insoluble or poorly soluble in an alkaline solution, having a repeating unit whose phenolic ydroxyl group is protected by a tertiary alkyl group, while soluble in an alkaline solution when the tertiary alkyl group is removed; (B) an acid generator; (C) a basic component; and (D) an organic solvent, and a solid component concentration is controlled so that the chemically amplified resist film having the film thickness of 10 to 100 nm is obtained by a spin coating method.
    Type: Grant
    Filed: November 23, 2009
    Date of Patent: August 28, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Akinobu Tanaka, Takanobu Takeda, Satoshi Watanabe
  • Patent number: 8252505
    Abstract: A resist composition including a base component (A) that exhibits changed solubility in an alkali developing solution under the action of acid, and an acid generator component (B) that generates acid upon exposure, wherein the acid generator component (B) includes an acid generator (B1) consisting of a compound represented by general formula (b1-2) shown below: [Chemical Formula 1] A+Z???(b1-2) wherein A+ represents an organic cation; and Z? represents an anionic cyclic group, wherein the cyclic group includes an ester linkage within the ring structure, two mutually different groups are bonded to the ring structure, one of these groups includes an ester linkage in which a carbon atom that constitutes part of the ester linkage is bonded directly to the ring structure, and the other group includes an anion moiety.
    Type: Grant
    Filed: February 16, 2009
    Date of Patent: August 28, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Keita Ishiduka, Kensuke Matsuzawa, Yoshiyuki Utsumi, Hiroaki Shimizu
  • Patent number: 8247160
    Abstract: A resist composition including a base component that exhibits changed solubility in an alkali developing solution under the action of acid, and an acid generator consisting of a compound represented by general formula (b1). In formula (b1), Y1 represents a fluorinated alkylene group of 1 to 4 carbon atoms, X represents an aliphatic cyclic group of 3 to 30 carbon atoms, R11? to R13? each represents an aryl group or alkyl group, provided that at least one of R11? to R13? is an aryl group having a substituent represented by general formula (b1-0), and two alkyl groups among R11? to R13? may be bonded to each other to form a ring with the sulfur atom in the formula. In formula (b1-0), R52 represents a chain-like or cyclic hydrocarbon group, and f and g each represents 0 or 1.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: August 21, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Akiya Kawaue, Hiroaki Shimizu, Tsuyoshi Nakamura
  • Patent number: 8241831
    Abstract: An acid generating agent represented by the following formula (1) or (2) is provided, which is included in chemically amplified resist compositions: wherein in the formula (1) and (2), X represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms and selected from alkyl, haloalkyl and alkylsulfonyl, which may have at least one hydrogen atom substituted by an ether group, an ester group, a carbonyl group, an acetal group, a nitrile group, a cyano group, a hydroxyl group, a carboxyl group or an aldehyde group, or represents a perfluoroalkyl group having 1 to 4 carbon atoms; R6 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a heteroatom selected from nitrogen, sulfur, fluorine and oxygen; m is an integer from 0 to 2; and A+ is an organic counterion.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: August 14, 2012
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Sung-Do Jung, Jin-Ho Kim, Jung-Hoon Oh, Hyun-Soon Lim
  • Patent number: 8216764
    Abstract: A positive resist composition including a resin component (A) which exhibits increased alkali solubility under action of acid and an acid-generator component (B) which generates acid upon exposure, the resin component (A) including a structural unit (a1) derived from an acrylate ester having a tertiary alkyl ester-type acid dissociable, dissolution inhibiting group containing an aliphatic monocyclic group and/or an aliphatic branched, tertiary alkyl ester-type acid dissociable, dissolution inhibiting group, and the acid-generator component (B) including an acid generator (B1) having a cation moiety represented by general formula (b?-1) shown below: wherein each of R1 and R2 independently represents a naphthyl group which may have a substituent; and R3 represents an alkyl group or an aryl group exclusive of a naphthyl group.
    Type: Grant
    Filed: May 18, 2007
    Date of Patent: July 10, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Masaru Takeshita
  • Patent number: 8206888
    Abstract: It is intended to provide a radiation-sensitive resin composition, which comprises a radiation-sensitive acid generator excellent in resolution performance, heat stability, and storage stability, suppresses fluctuations in line width and deterioration in pattern profile attributed to standing waves, and produces a resist pattern improved in nano edge roughness and LEF. The radiation-sensitive resin composition is characterized by (A) a radiation-sensitive acid generator comprising: a sulfonium salt compound typified by 2,4,6-trimethylphenyldiphenylsulfonium 2,4-difluorobenzenesulfonate, 2,4,6-trimethylphenyldiphenylsulfonium 4-trifluoromethylbenzenesulfonate, or the like; and a sulfonimide compound. It is preferred that the composition should further comprise (B) a resin typified by a 4-hydroxystyrene/4-t-butoxystyrene copolymer, a 4-hydroxystyrene/t-butyl (meth)acrylate, or the like.
    Type: Grant
    Filed: November 21, 2006
    Date of Patent: June 26, 2012
    Assignee: JSR Corporation
    Inventors: Yuuji Yada, Tomoki Nagai
  • Patent number: 8206886
    Abstract: A photosensitive composition comprises (A) a sulfonium or iodonium salt having an anion represented by one of formulae (I) and (II): wherein Y represents an alkylene group substituted with at least one fluorine atom, and R represents an alkyl group or a cycloalkyl group.
    Type: Grant
    Filed: January 25, 2005
    Date of Patent: June 26, 2012
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • 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
  • Patent number: 8187790
    Abstract: Disclosed are a polymer for a chemically amplified resist represented as and a resist composition using the same. In the above Chemical formula 1, X represents vinyl ether derivatives or olefin derivatives, at least one of R1, R2, R3, and R4 is an alkyl group with 1 to 30 carbon atoms containing at least one functional group of a hydrogen atom, an ether group, an ester group, a carbonyl group, an acetal group, an epoxy group, a nitryl group (—CN), and an aldehyde group, l, m, n, o and p respectively represent repeating units, l represents a real number of 0.05 to 0.5, m and n respectively represent real numbers of 0.1 to 0.7, o and p respectively represent real numbers of 0 to 0.7, and a sum of l, m, n, o and p is 1.
    Type: Grant
    Filed: April 2, 2009
    Date of Patent: May 29, 2012
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Hyunsang Joo, Jinho Kim, Yonghwa Hong, Changsoo Lee
  • Patent number: 8173353
    Abstract: The present invention provides a sulfonium compound represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, R1 represents a C5-C42 organic group having a ?-ketoester structure and A+ represents an organic counter ion, and a chemically amplified photoresist composition comprising the above-mentioned sulfonium compound and a resin comprising a structural unit having an acid-labile group and being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid.
    Type: Grant
    Filed: March 23, 2010
    Date of Patent: May 8, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Junji Shigematsu, Hanwoo Park
  • Patent number: 8173351
    Abstract: A compound shown by the following formula (1) can be used as a material for a radiation-sensitive composition capable of forming a resist film which effectively responds to electron beams or the like, exhibits low roughness, and can form a high precision minute pattern in a stable manner.
    Type: Grant
    Filed: January 8, 2008
    Date of Patent: May 8, 2012
    Assignee: JSR Corporation
    Inventors: Daisuke Shimizu, Ken Maruyama, Toshiyuki Kai, Tsutomu Shimokawa
  • Patent number: 8173350
    Abstract: An oxime compound represented by the formula (I): wherein Y represents an unsubstituted or substituted n-valent C6-C14 aromatic hydrocarbon group, n represents an integer of 1 to 6, R1 represents a C1-C30 aliphatic hydrocarbon group etc., R2 represents a linear or branched chain C1-C20 aliphatic hydrocarbon group etc., W represents —CO—O— etc., Q1 and Q2 each independently represent a fluorine atom etc., Z represents a C1-C20 halogenated aliphatic hydrocarbon group etc, and the resist composition containing the same.
    Type: Grant
    Filed: July 21, 2009
    Date of Patent: May 8, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Kazuhiko Hashimoto, Takashi Hiraoka, Ichiki Takemoto
  • Patent number: 8173354
    Abstract: A sulfonium salt having a triphenylsulfonium cation and a sulfite anion within the molecule is best suited as a photoacid generator in chemically amplified resist compositions. Upon exposure to high-energy radiation, the sulfonium salt generates a sulfonic acid, which facilitates efficient scission of acid labile groups in chemically amplified positive resist compositions. Because of substantial non-volatility under high vacuum conditions in the EB or EUV lithography, the risk of the exposure tool being contaminated is minimized.
    Type: Grant
    Filed: July 7, 2010
    Date of Patent: May 8, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi
  • Patent number: 8163463
    Abstract: A photoresist composition including an oxetane-containing compound represented by Formula 1 or 2, an oxirane-containing compound represented by Formula 3 or 4, a photoinitiator, and a solvent, a method of forming a pattern using the photoresist composition, and an inkjet print head including a polymerization product of the photoresist composition. The photoresist composition provides a polymerization product which resists formation of cracks due to an inner stress, and has excellent heat tolerance, excellent chemical resistance, excellent adhesiveness, and excellent durability.
    Type: Grant
    Filed: February 29, 2008
    Date of Patent: April 24, 2012
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Jin-baek Kim, Byung-ha Park, Kyu-sik Kim, Young-ung Ha, Su-min Kim
  • Patent number: 8163461
    Abstract: The invention provides various photoacid generator compounds and ionic components thereof. Photoresist compositions that include the ions and non-ionic photoacid generator compounds are also provided. The invention further provides methods of making and using the photoacid generator compounds and photoresist compositions disclosed herein. The compounds and compositions are useful as photoactive components in chemically amplified resist compositions for use in, for example, various microfabrication applications.
    Type: Grant
    Filed: April 9, 2009
    Date of Patent: April 24, 2012
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Yi Yi
  • Patent number: 8158326
    Abstract: A compound which generates a sulfonic acid having one or more —SO3H groups and one or more —SO2— bonds upon irradiation with an actinic ray or a radiation; a photosensitive composition containing the compound; and a method of pattern formation with the photosensitive composition.
    Type: Grant
    Filed: August 13, 2008
    Date of Patent: April 17, 2012
    Assignee: Fujifilm Corporation
    Inventors: Kunihiko Kodama, Kenji Wada, Kaoru Iwato
  • Patent number: 8158329
    Abstract: The present invention provides a compound represented by the formula (I): wherein P1, P2, P3, P4 and P5 each independently represents a hydrogen atom etc., and at least one selected from the group consisting of R1, R2, R3, R4, R5, R6, R7, R8 and R9 is the group represented by the formula (II): wherein X1 and X2 each independently represent a hydrogen atom etc., n represents an integer of 1 to 4, Z1 represents a C1-C6 alkyl group etc., and ring Y represents an alicyclic hydrocarbon group, and the others each independently represent a hydrogen atom, a C1-C6 alkyl group or a hydroxyl group, and a chemically amplified resist composition containing the same.
    Type: Grant
    Filed: December 4, 2009
    Date of Patent: April 17, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ichiki Takemoto, Nobuo Ando
  • Patent number: 8148044
    Abstract: A positive photosensitive composition includes at least one compound that when exposed to actinic rays or radiation, generates any of the sulfonic acids of general formula (I) and a resin whose solubility in an alkali developer is increased by the action of an acid, wherein each of X1 and X2 independently represents a fluorine atom or a fluoroalkyl group, R1 represents a group with a polycyclic structure, provided that the polycyclic structure may have a substituent, and R2 represents a hydrogen atom, a chain alkyl group, a monocyclic alkyl group, a group with a polycyclic structure or a monocyclic aryl group, provided that each of the chain alkyl group, monocyclic alkyl group, polycyclic structure and monocyclic aryl group may have a substituent, and provided that R1 and R2 may be bonded to each other to thereby form a polycyclic structure.
    Type: Grant
    Filed: October 29, 2009
    Date of Patent: April 3, 2012
    Assignee: Fujifilm Corporation
    Inventors: Shuhei Yamaguchi, Tomotaka Tsuchimura, Yuko Tada
  • Patent number: 8133653
    Abstract: A positive resist composition for forming a thick-film resist having a film thickness of 1 to 15 ?m, the composition comprising: a resin component (A) that includes a polymer compound (A1), which has a weight average molecular weight of 20,000 to 50,000, and includes a structural unit (a1) derived from a hydroxystyrene and a structural unit (a2) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group, an acid generator component (B) that generates acid upon exposure and includes an onium salt-based acid generator having an anion moiety represented by general formula (I): R4?SO3? (wherein, R4? represents a linear or branched alkyl group or fluoroalkyl group of 4 carbon atoms), and a nitrogen-containing organic compound (D) that includes a tertiary aliphatic amine.
    Type: Grant
    Filed: January 31, 2007
    Date of Patent: March 13, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroshi Shimbori, Masahiro Masujima, Toshihiro Yamaguchi, Sachiko Yoshizawa
  • Patent number: 8124310
    Abstract: A positive resist composition includes: (A) a resin containing a repeating unit represented by formula (I) or (I?) as defined in the specification, of which solubility in an alkali developer increases under an action of an acid; and (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation: and a pattern forming method uses the positive resist composition.
    Type: Grant
    Filed: September 26, 2008
    Date of Patent: February 28, 2012
    Assignee: Fujifilm Corporation
    Inventors: Shuji Hirano, Shinichi Sugiyama
  • Patent number: 8124313
    Abstract: A compound represented by general formula (I); and a compound represented by general formula (b1-1). wherein Q1 represents a divalent linkage group or a single bond; Y1 represents an alkylene group which may have a substituent or a fluorinated alkylene group which may have a substituent; X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent, and has an —SO2— bond in the structure thereof; M+ represents an alkali metal ion; and A+ represents an organic cation.
    Type: Grant
    Filed: January 22, 2010
    Date of Patent: February 28, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Akiya Kawaue, Hideo Hada, Hiroaki Shimizu, Tsuyoshi Nakamura
  • Patent number: 8110337
    Abstract: A polymerizable composition containing: (A) a binder polymer; (B) a compound having a polymerizable unsaturated group; and (C) a compound which has a triarylsulfonium salt structure and in which a sum of Hammett's a constants of all substituents bonded to the aryl skeleton is larger than 0.46.
    Type: Grant
    Filed: December 18, 2003
    Date of Patent: February 7, 2012
    Assignee: Fujifilm Corporation
    Inventor: Kazuto Shimada
  • Patent number: 8092976
    Abstract: A resist composition containing: a polymer having a group capable of decomposing under an action of an acid and having a weight average molecular weight of from 1,000 to 5,000, of which solubility in an alkali developer increases under an action of an acid; and a compound capable of generating a compound having a structure represented by the following formula (A-I) upon irradiation with actinic rays or radiation: Q1-X1—NH—X2-Q2??(A-I) wherein Q1 and Q2 each independently represents a monovalent organic group, provided that either one of Q1 and Q2 has a proton acceptor functional group, Q1 and Q2 may be combined with each other to form a ring and the ring formed may have a proton acceptor functional group; and X1 and X2 each independently represents —CO— or —SO2—.
    Type: Grant
    Filed: September 28, 2007
    Date of Patent: January 10, 2012
    Assignee: FUJIFILM Corporation
    Inventors: Sou Kamimura, Kenji Wada
  • Patent number: 8062829
    Abstract: A chemically amplified resist composition, comprising: a resin which includes a structural unit having an acid-labile group in a side chain, a structural unit represented by the formula (I) and a structural unit having a polycyclic lactone structure, and which is soluble in an organic solvent and insoluble or poorly soluble in an alkali aqueous solution but rendered soluble in an alkali aqueous solution by the action of an acid; and an acid generator represented by the formula (II). wherein X1 represents a hydrogen atom, a C1 to C4 alkyl group, etc., Y in each occurrence independently represent a hydrogen atom or an alkyl group, and n is an integer of 1 to 14, R1 to R4 independently represent a hydrogen atom, an alkyl group, etc., and A+ represents an organic counterion, E? represents CF3SO3—, C2F5SO3—, C4F9SO3—, etc., Y1 and Y2 independently represent a fluorine atom or a C1 to C6 perfluoroalkyl group.
    Type: Grant
    Filed: March 2, 2009
    Date of Patent: November 22, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsuhiro Hata, Yusuke Fuji, Takayuki Miyagawa
  • 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: 8053158
    Abstract: Disclosed herein are compositions useful in forming organic active patterns that may, in turn, be incorporated in organic memory devices. The compositions comprise N-containing conjugated electroconductive polymer(s), photoacid generator(s) and organic solvent(s) capable of dissolving suitable quantifies of both the electroconductive polymer and the photoacid generator. Also disclosed are methods for patterning organic active layers formed using one or more of the compositions to produce organic active patterns, portions of which may be arranged between opposed electrodes to provide organic memory cells. The methods include directly exposing and developing the organic active layer to obtain fine patterns without the use of a separate masking pattern, for example, a photoresist pattern, thereby tending to simplify the fabrication process and reduce the associated costs.
    Type: Grant
    Filed: January 19, 2007
    Date of Patent: November 8, 2011
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sang Kyun Lee, Won Jae Joo, Kwang Hee Lee, Tae Lim Choi, Myung Sup Jung
  • Patent number: 8048613
    Abstract: An alkali development-type solder resist includes (A) a carboxyl group-containing photosensitive resin obtained by reacting (a) a compound having two or more cyclic ether or thioether groups in the molecule with (b) an unsaturated monocarboxylic acid, reacting the product with (c) a polybasic acid anhydride, reacting the resulting resin with (d) a compound having a cyclic ether group and an ethylenic unsaturated group in the molecule, and reacting the product additionally with (c) a polybasic acid anhydride, (B) an oxime ester-based photopolymerization initiator containing a specific oxime ester group, (C) a compound having two or more ethylenic unsaturated groups in the molecule, and (D) a thermosetting component, wherein the dry film obtained by applying the composition has an absorbance of 0.3 to 1.2 per 25 ?m of the film thickness at a wavelength of 350 to 375 nm.
    Type: Grant
    Filed: October 13, 2008
    Date of Patent: November 1, 2011
    Assignee: Taiyo Ink Mfg. Co., Ltd.
    Inventors: Nobuhito Itoh, Yoko Shibasaki, Kenji Kato, Masao Arima
  • Patent number: 8043786
    Abstract: The invention provides novel acid generators which are unproblematic in combustibility and accumulation inside the human body and can generate acids having high acidities and high boiling points and exhibiting properly short diffusion lengths in resist coating films and which permit the formation of resist patterns excellent smoothness with little dependence on the denseness of a mask pattern; sulfonic acids generated from the acid generators; sulfonyl halides useful as raw material in the synthesis of the acid generators; and radiation-sensitive resin compositions containing the acid generators. The acid generators have structures represented by the general formula (I), wherein R1 is a monovalent substituent such as alkoxycarbonyl, alkylsulfonyl, or alkoxysulfonyl; R2 to R4 are each hydrogen or alkyl; k is an integer of 0 or above; and n is an integer of 0 to 5.
    Type: Grant
    Filed: February 20, 2004
    Date of Patent: October 25, 2011
    Assignee: JSR Corporation
    Inventors: Satoshi Ebata, Yong Wang, Isao Nishimura
  • Patent number: 8039200
    Abstract: A photosensitive composition comprises (A) a sulfonium or iodonium salt having an anion represented by one of formulae (I) and (II): wherein Y represents an alkylene group substituted with at least one fluorine atom, and R represents an alkyl group or a cycloalkyl group.
    Type: Grant
    Filed: August 10, 2010
    Date of Patent: October 18, 2011
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 8034546
    Abstract: The use as a resist material of a methanofullerene derivative having a plurality of open-ended addends, and to a method for forming a patterned resist layer on a substrate using the methanofullerene derivatives. The methanofullerene derivatives can be represented by the formal C2x(CR1R2)m where x is at least 10, m is at least 2, each addend represented by CR1R2 is the same or different, and wherein each R1 and R2 is each a monovalent organic group, or a divalent organic group which forms a ring structure by being joined to the fullerene shell, or where both R1 and R2 of an addend are divalent groups, they may be mutually joined to form a ring structure, save that at least two of R1 or two of R2 are monovalent, or a mixture of such derivatives. The use of any methanofullerene derivative which has been chemically amplified for formation of a patterned resist layer.
    Type: Grant
    Filed: September 19, 2005
    Date of Patent: October 11, 2011
    Assignee: The University of Birmingham
    Inventors: Alex Robinson, Jon Andrew Preece, Richard Edward Palmer
  • Patent number: 8034533
    Abstract: Fluorine-free photoacid generators and photoresist compositions containing fluorine-free photoacid generators are enabled as alternatives to PFOS/PFAS photoacid generator-containing photoresists. The photoacid generators are characterized by the presence of a fluorine-free heteroaromatic sulfonate anionic component. The photoacid generators preferably contain an onium cationic component, more preferably a sulfonium cationic component. The photoresist compositions preferably contain an acid sensitive imaging polymer. The compositions are especially useful for forming material patterns using 193 nm (ArF) imaging radiation.
    Type: Grant
    Filed: January 16, 2008
    Date of Patent: October 11, 2011
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8029975
    Abstract: A resist composition and a method for forming a patterned feature on a substrate. The composition comprises a molecular glass having at least one fused polycyclic moiety and at least one base soluble functional group protected with an acid labile protecting group, and a photosensitive acid generator. The method includes providing a composition including a photosensitive acid generator and a molecular glass having at least one fused polycyclic moiety and at least one base soluble functional group protected with an acid labile protecting group, forming a film of the composition on the substrate, patternwise imaging the film, wherein at least one region of the film is exposed to radiation or a beam of particles, resulting in production of an acid catalyst in the exposed region, baking the film, developing the film, resulting in removal of base-soluble exposed regions, wherein a patterned feature from the film remains following the removal.
    Type: Grant
    Filed: July 24, 2009
    Date of Patent: October 4, 2011
    Assignee: International Business Machines Corporation
    Inventors: James J. Bucchignano, Wu-Song Huang, Pushkara R. Varanasi, Roy R. Yu
  • Patent number: 8029971
    Abstract: Compositions, a method, and a photopatternable blend. The compositions include a blend of a first and a second polymer. The first polymer is a substituted silsesquioxane copolymer. The second polymer is a substituted silsesquioxane polymer. The second polymer is configured to undergo chemical crosslinking with the first polymer, the second polymer, or a combination thereof, upon exposure to light, thermal energy, or a combination thereof. The compositions include a photosensitive acid generator. The method includes forming a film. The film is patternwise imaged, and at least one region is exposed to radiation. After the imaging, the film is baked, wherein at least one exposed region is rendered substantially soluble. After the baking, the film is developed, wherein a relief pattern remains. The relief pattern is exposed to radiation. The relief pattern is baked. The relief pattern is cured. A chemically amplified positive-tone photopatternable blend is also described.
    Type: Grant
    Filed: March 13, 2008
    Date of Patent: October 4, 2011
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Phillip Joe Brock, Blake W. Davis, Qinghuang Lin, Robert D. Miller, Alshakim Nelson, Ratnam Sooriyakumaran
  • Patent number: 8021822
    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 specific recurring units, represented by formula (1). The acid generator (B) is a specific sulfonium salt compound. When processed by lithography, the composition is improved in resolution and forms a pattern with a satisfactory mask fidelity and a minimal LER. Herein R1 is H or methyl, m is 1 or 2, and n is 1 or 2.
    Type: Grant
    Filed: January 16, 2009
    Date of Patent: September 20, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
  • Patent number: 8021823
    Abstract: There is provided a positive resist composition, including a base component (A) which exhibits increased solubility in an alkali developing solution under action of an acid, and an acid generator component (B) which generates an acid upon exposure, wherein the base component (A) includes a polymeric compound (A1) containing a structural unit (a0) represented by the general formula (a0-1) shown below: (wherein, R1 represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; A represents a bivalent linking group; B represents a bivalent linking group; and R2 represents an acid dissociable, dissolution inhibiting group).
    Type: Grant
    Filed: February 18, 2009
    Date of Patent: September 20, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Takahiro Dazai, Daiju Shiono, Tomoyuki Hirano
  • Patent number: 8017302
    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 specific recurring units, represented by formula (1). The acid generator (B) is a specific sulfonium salt compound. When processed by lithography, the composition is improved in resolution and forms a pattern with a minimal LER. Herein R1 is H or methyl, R2 is an acid labile group, R3 is CO2R4 when X is CH2, R3 is H or CO2R4 when X is O, R4 is a monovalent C1-C20 hydrocarbon group, and m is 1 or 2.
    Type: Grant
    Filed: January 16, 2009
    Date of Patent: September 13, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
  • Patent number: 8003294
    Abstract: A photosensitive composition comprises: (A) a compound capable of generating an acid represented by formula (I) upon irradiation with actinic ray or radiation; and (B) a resin that decomposes by the action of an acid to its increase solubility in an alkali developer wherein Ra represents an alkyl group substituted with a fluorine atom, or an aryl group substituted with a fluorine atom or a group having a fluorine atom; Rb represents an alkyl group not substituted with a fluorine atom on ?-position of the alkyl group, or an aryl group not substituted with a fluorine atom or a group having a fluorine atom.
    Type: Grant
    Filed: March 10, 2008
    Date of Patent: August 23, 2011
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: RE43560
    Abstract: A positive photosensitive composition comprising (A) a compound capable of generating a fluorine-substituted alkanesulfonic acid having 2 to 4 carbon atoms by irradiation of actinic rays or radiation, (B) a resin having a monocyclic or polycyclic alicyclic hydrocarbon structure and being decomposed by the action of an acid to increase solubility in an alkali developer, (C) a basic compound, and (D) a fluorine and/or silicon surfactant.
    Type: Grant
    Filed: December 30, 2009
    Date of Patent: July 31, 2012
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Toshiaki Aoai