Two Of The Cyclos Share At Least Three Ring Members Or Ring Carbon Is Shared By The Three Cyclos (e.g., Bridged Or Peri Compounds, Etc.) Patents (Class 549/300)
  • Patent number: 9005874
    Abstract: There are provided a novel compound, a polymeric compound, a resist composition, an acid generator and a method of forming a resist pattern the compound represented by general formula (1-1): wherein each of R1 and R3 independently represents a single bond or a divalent linking group; A represents a divalent linking group; each of R2 and R4 independently represents a hydroxyl group, a hydrocarbon group which may have a substituent, or a group represented by general formula (1-an1), (1-an2) or (1-an3), provided that at least one of R2 and R4 represents a group represented by general formula (1-an1), (1-an2) or (1-an3); and n0 is preferably 0 or 1, and wherein Y1 represents a single bond or —SO2—; R5 represents a linear or branched monovalent hydrocarbon group of 1 to 10 carbon atoms, cyclic monovalent hydrocarbon group of 3 to 20 carbon atoms or monovalent hydrocarbon group of 3 to 20 carbon atoms having a cyclic partial structure which may be substituted with a fluorine atom; and M+ represents an organic ca
    Type: Grant
    Filed: April 18, 2012
    Date of Patent: April 14, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshitaka Komuro, Yoshiyuki Utsumi, Akiya Kawaue, Masatoshi Arai
  • 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: 8916330
    Abstract: The present invention provides a resist composition giving a resist pattern excellent in CD uniformity and focus margin. A chemically amplified photoresist composition comprises a resin (A) and an acid generator (B), and the resin (A) contains, as a part or an entirety thereof, a copolymer (A1) which is obtained by polymerizing at least: a (meth)acrylic monomer (a1) having C5-20 alicyclic hydrocarbon group which becomes soluble in an aqueous alkali solution by the action of an acid; a (meth)acrylic monomer (a2) having a hydroxy group-containing adamantyl group; and a (meth)acrylic monomer (a3) having a lactone ring, and the copolymer (A1) has a weight-average molecular weight of 2500 or more and 5000 or less, and a content of the copolymer (A1) is not less than 50 parts by mass with respect to 100 parts by mass of the resin (A).
    Type: Grant
    Filed: June 23, 2010
    Date of Patent: December 23, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takashi Hiraoka
  • 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: 8883394
    Abstract: The present invention provides a resist composition giving a resist pattern excellent in CD uniformity and focus margin. A chemically amplified photoresist composition comprises a resin (A) and an acid generator (B), and the resin (A) contains, as a part or an entirety thereof, a copolymer (A1) which is obtained by polymerizing at least: a (meth)acrylic monomer (a1) having C5-20 alicyclic hydrocarbon group which becomes soluble in an aqueous alkali solution by the action of an acid; a (meth)acrylic monomer (a2) having a hydroxy group-containing adamantyl group; and a (meth)acrylic monomer (a3) having a lactone ring, and the copolymer (A1) has a weight-average molecular weight of 2500 or more and 5000 or less, and a content of the copolymer (A1) is not less than 50 parts by mass with respect to 100 parts by mass of the resin (A).
    Type: Grant
    Filed: June 23, 2010
    Date of Patent: November 11, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takashi Hiraoka
  • Patent number: 8835097
    Abstract: There is disclosed a sulfonium salt shown by the following general formula (1). There can be a sulfonium salt capable of introducing an acid-generating unit generating an acid having an appropriate acid strength and not impairing adhesion with a substrate into a base polymer; a polymer using the said sulfonium salt; a chemically amplified resist composition using the said polymer as a base polymer; and a patterning process using the said chemically amplified resist composition.
    Type: Grant
    Filed: May 21, 2012
    Date of Patent: September 16, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Daisuke Domon, Keiichi Masunaga, Satoshi Watanabe
  • Publication number: 20140220492
    Abstract: A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, including a base component containing a polymeric compound having a structural unit derived from a compound represented by general formula (a0-1). R1 and R2 each independently represents a group represented by general formula (a0-2) or a functional group; V1 and V2 each represents a single bond or an alkylene group of C1 to C10 which may have a substituent; Y1 represents a single bond or a divalent linking group; Y2 represents a fluorinated alkylene group of C1 to C4 which may have a substituent; L1 represents O or a group represented by —NR?1—(R?1 represents H or an alkyl group of C1 to C5); Mm+ represents an organic cation having a valency of m; and m represents an integer of 1 or more.
    Type: Application
    Filed: February 3, 2014
    Publication date: August 7, 2014
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takaaki Kaiho, Yoshitaka Komuro
  • Publication number: 20140178821
    Abstract: A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, including a base component (A) which exhibits changed solubility in a developing solution under action of acid, and a photo-decomposable quencher (D0) containing a compound represented by general formula (d0) shown below. In the formula, R1 represents a hydrocarbon group of 4 to 20 carbon atoms which may have a substituent; Y1 represents a single bond or a divalent linking group; R2 and R3 each independently represents a substituent of 0 to 20 carbon atoms other than a fluorine atom; one of R2 and R3 may form a ring with Y1; Mm+ represents an organic cation having a valency of m; and m represents an integer of 1 or more.
    Type: Application
    Filed: December 18, 2013
    Publication date: June 26, 2014
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Takaaki Kaiho, Tsuyoshi Nakamura
  • Patent number: 8754242
    Abstract: Compounds of formula (I) wherein the substituents are as defined in claim 1, are suitable for use as herbicides.
    Type: Grant
    Filed: August 6, 2008
    Date of Patent: June 17, 2014
    Assignees: Syngenta Crop Protection LLC, Syngenta Limited
    Inventors: Melloney Tyte, Christopher John Matthews, Gavin John Hall, William Guy Whittingham, Jeffrey Steven Wailes, James Nicholas Scutt, Stephane André Marie Jeanmart, Russell Colin Viner
  • Publication number: 20140154625
    Abstract: A radiation-sensitive resin composition includes a compound represented by a formula (1), and a base polymer. In the formula (1), R1 is a group represented by a formula (a1), and M+ represents a radiation-degradable monovalent cation. In the formula (a1), R2 represents a substituted or unsubstituted chain hydrocarbon group having 1 to 30 carbon atoms, or the like. R3 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms, or the like. R41 represents —CO—, or the like. R42 represents —CO—, or the like. m is an integer of 0 to 2. n is an integer of 0 to 1. A site denoted by * is a binding site with —O— in the formula (1).
    Type: Application
    Filed: July 8, 2013
    Publication date: June 5, 2014
    Inventor: Ken MARUYAMA
  • Publication number: 20140134539
    Abstract: To provide an alcohol compound containing fewer impurities at a high yield by conducting the following steps: a hydroboration process in which a reaction mixture is obtained by reacting in a solvent a compound represented by formula (C) and a boron agent selected from a group of diborane and borane complexes; and an oxidation process in which the pH of the reaction mixture is set at 0.5 to 4, which is conducted after treating the reaction mixture with hydrogen peroxide. In the formula, A1 to A6 are each independently a hydrogen atom, methyl group or ethyl group, and X is an oxygen atom, sulfur atom, methylene group or ethylene group.
    Type: Application
    Filed: June 14, 2012
    Publication date: May 15, 2014
    Applicant: Mitsubishi Rayon Co., Ltd.
    Inventors: Satoshi Sakuma, Masashi Serizawa, Atsushi Yasuda, Nobushi Yada, Shinichi Maeda
  • Patent number: 8658806
    Abstract: The present invention relates to a process of preparation of optically active antrocin. At first, to introduce the correct configuration of trans-decalone, alkyl aluminum/TMSCN was used to react with decalenone. The resulting racemic nitrile-decalone was resolved with chiral diol by ketalization to produce two chromatography separable diasteromers. After a simple column chromatography, optically pure compounds were obtained. Formylation was a critical step for the lactone formation. The rest of the synthesis is straight forward through oxidation and olefination. Accordingly, the total synthesis was completed in 10 steps with 7% overall yield from commercially available 6-methoxy-2-tetralone.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: February 25, 2014
    Assignee: Deyew Biotech Corp.
    Inventors: Dar-Fu Tai, Venkatachalam Angamuthu, Yew-Min Tzeng
  • Publication number: 20130310451
    Abstract: The present invention discloses novel compounds useful for the inhibition of IL-6/STAT signaling and/or PI3K/NF-?B signaling in the treatment of associated diseases or conditions, e.g. cancer. A pharmaceutical composition comprising such novel compounds, its use and a method thereof, is also disclosed.
    Type: Application
    Filed: July 18, 2011
    Publication date: November 21, 2013
    Applicant: GLACTONE PHARMA DEVELOPMENT AB
    Inventors: Ritha Gidlöf, Martin Johansson, Olov Sterner, Eduardo Muñoz
  • Publication number: 20130309614
    Abstract: There is provided a resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution by the action of acid, including a base component (A) which exhibits changed solubility in a developing solution by the action of acid, wherein the base component (A) contains a polymeric compound (A1) having a structural unit (a0) represented by general formula (a0) shown below. In the formula, A? represents an oxygen atom, a sulfur atom or an alkylene group of 1 to 5 carbon atoms which may contain an oxygen atom or a sulfur atom; R1 represents a lactone-containing cyclic group, an —SO2— containing cyclic group or a carbonate-containing cyclic group; and W2 represents a group which is formed by polymerization reaction of a group containing a polymerizable group.
    Type: Application
    Filed: May 15, 2013
    Publication date: November 21, 2013
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Masatoshi Arai, Takahiro Dazai, Yoshitaka Komuro
  • Patent number: 8580478
    Abstract: The invention pertains to a compound generating an acid of the formula I or II, for instance corresponding sulfonium and iodonium salts, as well as corresponding sulfonyloximes wherein X is CH2 or CO; Y is O, NR4, S, O(CO), O(CO)O, O(CO)NR4, OSO2, O(CS), or O(CS)NR4; R1 is for example C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18alkyl, interrupted C2-C18alkyl, interrupted C3-C30cycloalkyl, interrupted C3-C30cycloalkyl-C1-C18alkyl, interrupted C4-C30cycloalkenyl, phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, fluorenyl or heteroaryl, all unsubstituted or are substituted; or R1 is NR12R13; R2 and R3 are for example C3-C30cycloalkylene, C3-C30cycloalkyl-C1-C18alkylene, C1-C18alkylene, C1-C10haloalkylene, C2-C12alkenylene, C4-C30cycloalkenylene, phenylene, naphthylene, anthracylene, phenanthrylene, biphenylene or heteroarylene; all unsubstituted or substituted; R4 is for example C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18al
    Type: Grant
    Filed: February 16, 2011
    Date of Patent: November 12, 2013
    Assignee: BASF SE
    Inventors: Hitoshi Yamato, Toshikage Asakura, Akira Matsumoto, Keita Tanaka, Yuichi Nishimae
  • Publication number: 20130295505
    Abstract: A radiation-sensitive resin composition includes a compound represented by a formula (1), and a base polymer. In the formula (1), R1 is a group represented by a formula (a1), and M+ represents a radiation-degradable monovalent cation. In the formula (a1), R2 represents a substituted or unsubstituted chain hydrocarbon group having 1 to 30 carbon atoms, or the like. R3 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 30 carbon atoms, or the like. R41 represents —CO—, or the like. R42 represents —CO—, or the like. m is an integer of 0 to 2. n is an integer of 0 to 1. A site denoted by * is a binding site with —O— in the formula (1).
    Type: Application
    Filed: July 8, 2013
    Publication date: November 7, 2013
    Inventor: Ken MARUYAMA
  • Publication number: 20130288179
    Abstract: A radiation-sensitive resin composition includes a compound represented by a formula (1), and a polymer that includes a structural unit having an acid-labile group. R1 and R4 each independently represent a hydrogen atom, or the like. R2 and R3 each independently represent a hydrogen atom or the like. X1 and X2 each independently represent a hydrogen atom, or the like, or X1 and X2 taken together represent —S—, —O—, —SO2—, or the like. A represents an ethanediyl group, wherein at least one hydrogen atom included in X1, X2 and A is substituted by —Y—SO3?M+. Y represents an alkanediyl group having 1 to 10 carbon atoms, or the like. M+ represents a monovalent onium cation. In the case where —Y—SO3?M+ is present in a plurality of number, a plurality of Ys are each identical or different and a plurality of M+s are each identical or different.
    Type: Application
    Filed: June 27, 2013
    Publication date: October 31, 2013
    Inventors: Kazuo NAKAHARA, Ken MARUYAMA
  • Patent number: 8557500
    Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, L2 represents a single bond or a C1-C6 alkanediyl group in which one or more —CH2— can be replaced by —O— or —CO—, Y represents a C3-C18 alicyclic hydrocarbon group which can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O—, —CO— or —SO2—, and Z+ represents an organic counter ion.
    Type: Grant
    Filed: February 28, 2012
    Date of Patent: October 15, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Takahiro Yasue
  • Publication number: 20130260315
    Abstract: A radiation-sensitive resin composition includes a polymer component that includes one or more types of polymers, and a radiation-sensitive acid generator. At least one type of the polymer of the polymer component includes a first structural unit represented by a following formula (1). R1 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group. R2 represents a linear alkyl group having 5 to 21 carbon atoms. Z represents a divalent alicyclic hydrocarbon group or an aliphatic heterocyclic group having a ring skeleton which has 4 to 20 atoms. A part or all of hydrogen atoms included in the alicyclic hydrocarbon group and the aliphatic heterocyclic group represented by Z are not substituted or substituted.
    Type: Application
    Filed: May 30, 2013
    Publication date: October 3, 2013
    Inventors: Mitsuo SATO, Takehiko NARUOKA
  • Publication number: 20130260316
    Abstract: A radiation-sensitive resin composition includes a compound represented by a formula (1), and a base polymer. A represents —CO— or —CH2—. R1 represents a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group having 3 to 30 ring atoms, or a combination of a first group and a second group. The first group is —CO—, —COO—, —OCO—, —O—CO—O—, —NHCO—, —CONH—, —NH—CO—O—, —O—CO—NH—, —NH—, —S—, —SO—, —SO2—, —SO2—O— or a combination thereof, and the second group is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group having 3 to 30 ring atoms or a combination thereof. A part or all of hydrogen atoms included in the hydrocarbon group and the heterocyclic group are not substituted or substituted. M+ represents a monovalent cation.
    Type: Application
    Filed: May 30, 2013
    Publication date: October 3, 2013
    Inventor: Ken MARUYAMA
  • Publication number: 20130230802
    Abstract: To provide an acrylamide derivative which can form a structural unit of a polymer to be incorporated into a photoresist composition, a polymer produced through polymerization of a raw material containing the acrylamide derivative, and a photoresist composition which contains the polymer and which, as compared with the case of conventional ones, realizes formation of a high-resolution resist pattern having improved LWR. The invention provides an acrylamide derivative represented by the following formula (1): wherein R1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group; W represents a C1 to C10 alkylene group or a C3 to C10 cycloalkylene group; R2 represents a cyclic group having 3 to 20 ring-forming atoms and represented by the following formula (2): wherein X represents an oxygen atom or >N—R3; R3 represents a hydrogen atom or a C1 to C5 alkyl group; Y represents >C?O or >S(?O)n; and n is an integer of 0 to 2.
    Type: Application
    Filed: August 25, 2011
    Publication date: September 5, 2013
    Applicant: KURARAY CO., LTD.
    Inventors: Ichihiro Aratani, Takashi Fukumoto
  • Publication number: 20130231491
    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: Application
    Filed: March 20, 2013
    Publication date: September 5, 2013
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventor: Shin-Etsu Chemical Co., Ltd.
  • Patent number: 8481242
    Abstract: A salt represented by the formula (X): wherein Q1 and Q2, L1 and L2, ring W1, R5, w, v, Z+ and W10 are defined in the specification.
    Type: Grant
    Filed: November 16, 2010
    Date of Patent: July 9, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Mitsuyoshi Ochiai, Masako Sugihara
  • Publication number: 20130171567
    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: Application
    Filed: December 12, 2012
    Publication date: July 4, 2013
    Applicant: ROHM AND HAAS ELECTRONIC MATERIALS LLC
    Inventor: Rohm and Haas Electronic Materials LLC
  • Publication number: 20130164675
    Abstract: The invention provides a novel acrylic ester derivative which can form a structural unit of a polymer to be incorporated into a photoresist composition; a polymer produced through polymerization of a raw material containing the acrylic ester derivative; and a photoresist composition which contains the polymer and which, as compared with the case of conventional ones, realizes formation of a high-resolution resist pattern having improved LWR.
    Type: Application
    Filed: September 2, 2011
    Publication date: June 27, 2013
    Applicant: KURARAY CO., LTD.
    Inventors: Osamu Nakayama, Manabu Yada
  • Publication number: 20130122426
    Abstract: A radiation-sensitive resin composition that provides a resist coating film in a liquid immersion lithography process is provided, the radiation-sensitive resin composition being capable of exhibiting a great dynamic contact angle during exposure, whereby the surface of the resist coating film can exhibit a superior water draining property, and the radiation-sensitive resin composition being capable of leading to a significant decrease in the dynamic contact angle during development, whereby generation of development defects can be inhibited, and further shortening of a time period required for change in a dynamic contact angle is enabled. A radiation-sensitive resin composition including (A) a fluorine-containing polymer having a structural unit (I) that includes a group represented by the following formula (1), and (B) a radiation-sensitive acid generator.
    Type: Application
    Filed: May 19, 2011
    Publication date: May 16, 2013
    Applicant: JSR CORPORATION
    Inventors: Hitoshi Osaki, Yusuke Asano, Mitsuo Sato, Tomoki Nagai
  • Publication number: 20130096324
    Abstract: The present invention relates to a process of preparation of optically active antrocin. At first, to introduce the correct configuration of trans-decalone, alkyl aluminum/TMSCN was used to react with decalenone. The resulting racemic nitrile-decalone was resolved with chiral diol by ketalization to produce two chromatography separable diasteromers. After a simple column chromatography, optically pure compounds were obtained. Formylation was a critical step for the lactone formation. The rest of the synthesis is straight forward through oxidation and olefination. Accordingly, the total synthesis was completed in 10 steps with 7% overall yield from commercially available 6-methoxy-2-tetralone.
    Type: Application
    Filed: September 14, 2012
    Publication date: April 18, 2013
    Applicant: DEYEW BIOTECH CORP.
    Inventors: Dar-fu TAI, Venkatachalam ANGAMUTHU, Yew-min TZENG
  • Publication number: 20130084525
    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: Application
    Filed: September 28, 2012
    Publication date: April 4, 2013
    Applicant: ROHM AND HAAS ELECTRONIC MATERIALS LLC
    Inventor: Rohm and Haas Electronic Materials LLC
  • Publication number: 20120308920
    Abstract: There is disclosed a sulfonium salt shown by the following general formula (1). There can be a sulfonium salt capable of introducing an acid-generating unit generating an acid having an appropriate acid strength and not impairing adhesion with a substrate into a base polymer; a polymer using the said sulfonium salt; a chemically amplified resist composition using the said polymer as a base polymer; and a patterning process using the said chemically amplified resist composition.
    Type: Application
    Filed: May 21, 2012
    Publication date: December 6, 2012
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Daisuke DOMON, Keiichi MASUNAGA, Satoshi WATANABE
  • Publication number: 20120276482
    Abstract: A radiation sensitive resin composition includes a first polymer having a group represented by a following formula (1), and a radiation sensitive acid generator. n is an integer of 2 to 4. X represents a single bond or a bivalent organic group. A represents a (n+1) valent linking group. Each Q independently represents a group that includes an alkali-dissociable group.
    Type: Application
    Filed: April 27, 2012
    Publication date: November 1, 2012
    Applicant: JSR Corporation
    Inventors: Takakazu Kimoto, Mitsuo Sato, Yusuke Asano, Tomohiro Kakizawa
  • Publication number: 20120245113
    Abstract: The use or methods of use of extracts comprising one or more special clerodane compounds against inflammatory (including allergic) diseases or conditions, as well as novel compounds of this type, said clerodane derivatives for use against inflammatory (including allergic) diseases or conditions, pharmaceutical formulations comprising them especially for use against inflammatory disease or conditions, and related embodiments; said extract and/or compound(s) for use in the treatment or in the preparation of a medicament (including a nutraceutical) for the prophylactic and/or therapeutic treatment of said disease or condition, as well as their preparation; pharmaceutical or nutraceutical formulations comprising said extract and/or natural compound(s) which are useful in said prophylactic and/or therapeutic treatment, and related embodiments.
    Type: Application
    Filed: February 22, 2012
    Publication date: September 27, 2012
    Applicant: BIOTROPICS MALAYSIA BHD
    Inventors: Matthias GEHLING, Torsten GROTHE, Ernst ROEMER, Peter REINEMER, Kathrin REINHARDT, Annie GEORGE, Nur Hanisah MOHTAR, Noorsyarida Mohd Sapiai
  • 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
  • Publication number: 20120184754
    Abstract: Compounds represented by Formula I are provided that include synthetic transtaganolide and basiliolide products. Derivatives of these compounds and methods of synthesis are also provided.
    Type: Application
    Filed: January 18, 2012
    Publication date: July 19, 2012
    Inventors: Hosea Nelson, Kei Murakami, Scott C. Virgil, Brian M. Stoltz, Jonathan R. Gordon
  • Publication number: 20120164580
    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: Application
    Filed: March 2, 2012
    Publication date: June 28, 2012
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Publication number: 20120164582
    Abstract: A radiation-sensitive composition includes a photoacid generator shown by a general formula (0-1a). Each of R0 individually represents a substituted or unsubstituted organic group which includes a carbon atom, a hydrogen atom, and an oxygen atom, and which includes at least one ester bond, and M+ represents a monovalent onium cation. A compound is shown by a general formula (0). R represents a substituted or unsubstituted organic group which includes a carbon atom, a hydrogen atom, and an oxygen atom, and which includes at least one ester bond, and M+ represents a monovalent onium cation.
    Type: Application
    Filed: March 8, 2012
    Publication date: June 28, 2012
    Applicant: JSR Corporation
    Inventor: Ken MARUYAMA
  • Patent number: 8114570
    Abstract: Photoacid generators generate sulfonic acids of formula (1a) upon exposure to high-energy radiation. ROC(?O)R1—COOCH2CF2SO3?H+??(1a) RO is OH or C1-C20 organoxy, R1 is a divalent C1-C20 aliphatic group or forms a cyclic structure with RO. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.
    Type: Grant
    Filed: March 24, 2009
    Date of Patent: February 14, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe, Koji Hasegawa, Masaki Ohashi
  • Patent number: 8106222
    Abstract: A fluorine-containing ether compound with a fluorine content increased, the fluorine content being enhanced by fluorinating a polymer including a repeating unit represented by the following Formula (I): wherein Rh1 represents a divalent linkage group; Rf2 represents an perfluoroalkylene group; each of Rf3 and Rf4 independently represents a fluorine atom, a perfluoroalkyl group or a perfluoroalkoxy group, and any two of Rf2, Rf3 and Rf4 may be combined with each other to form a ring.
    Type: Grant
    Filed: April 9, 2008
    Date of Patent: January 31, 2012
    Assignee: Fujifilm Corporation
    Inventors: Takayuki Ito, Toshimitsu Sakuma
  • Publication number: 20110287362
    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) represented by general formula (b1-1) shown below (in the formula, RX represents a divalent aliphatic group of 3 to 20 carbon atoms; RY represents a monovalent aliphatic group of 3 to 20 carbon atoms having —C(?O)—O— or —S(?O)2—; each of R1 and R2 independently represents a divalent linking group; and Z+ represents a monovalent organic cation).
    Type: Application
    Filed: May 12, 2011
    Publication date: November 24, 2011
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Kazushige Dohtani
  • Publication number: 20110250538
    Abstract: New methods are provided for synthesis of photoacid generator compounds (“PAGs”), new photoacid generator compounds and photoresist compositions that comprise such PAG compounds. In a particular aspect, sulfonium-containing (S+) photoacid generators and methods of synthesis of sulfonium photoacid generators are provided.
    Type: Application
    Filed: December 10, 2010
    Publication date: October 13, 2011
    Applicant: Rohm and Haas Electronic Materials LLC
    Inventors: Mingqi LI, Emad AQAD, Cong LIU, Joseph MATTIA, Cheng-Bai XU, George G. BARCLAY
  • Publication number: 20110217654
    Abstract: The invention pertains to a compound generating an acid of the formula I or II, for instance corresponding sulfonium and iodonium salts, as well as corresponding sulfonyloximes wherein X is CH2 or CO; Y is O, NR4, S, O(CO), O(CO)O, O(CO)NR4, OSO2, O(CS), or O(CS)NR4; R1 is for example C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18alkyl, interrupted C2-C18alkyl, interrupted C3-C30cycloalkyl, interrupted C3-C30cycloalkyl-C1-C18alkyl, interrupted C4-C30cycloalkenyl, phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, fluorenyl or heteroaryl, all unsubstituted or are substituted; or R1 is NR12R13; R2 and R3 are for example C3-C30cycloalkylene, C3-C30cycloalkyl-C1-C18alkylene, C1-C18alkylene, C1-C10haloalkylene, C2-C12alkenylene, C4-C30cycloalkenylene, phenylene, naphthylene, anthracylene, phenanthrylene, biphenylene or heteroarylene; all unsubstituted or substituted; R4 is for example C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18al
    Type: Application
    Filed: February 16, 2011
    Publication date: September 8, 2011
    Applicant: BASF SE
    Inventors: Hitoshi Yamato, Toshikage Asakura, Akira Matsumoto, Keita Tanaka, Yuichi Nishimae
  • Publication number: 20110117495
    Abstract: A salt represented by the formula (X): wherein Q1 and Q2 each independently represent a fluorine atom etc., L1 and L2 independently each represent a C1-C17 divalent saturated hydrocarbon group, ring W1 represents a C3-C36 saturated hydrocarbon ring, R2 is independently in each occurrence a hydroxyl group etc., s represents an integer of 0 to 2, Z+ represents an organic counter ion, and W10 represents a group represented by the formula (X-1): wherein ring W2 represents a C4-C36 saturated hydrocarbon ring in which one or more —CH2— can be replaced by —O— or —CO—, with the proviso that at least one —CH2— in the C4-C36 saturated hydrocarbon ring is replaced by —CO—, R3 is independently in each occurrence a C1-C6 alkyl group etc., and t represents an integer of 0 to 2, or a group represented by the formula (X-2): wherein ring W3 represents a C3-C36 saturated hydrocarbon ring, R4 is independently in each occurrence a hydroxyl group etc., R5 is independently in each occurrence a C1-C6 alkyl group etc.
    Type: Application
    Filed: November 16, 2010
    Publication date: May 19, 2011
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Koji ICHIKAWA, Mitsuyoshi OCHIAI, Masako SUGIHARA
  • Publication number: 20110117493
    Abstract: A salt represented by the formula (X): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, ring W1 represents a C4-C36 lactone ring, R3 is a C1-C6 alkyl group etc., t represents an integer of 0 to 2, Z+ represents an organic counter ion, and W10 represents a group represented by the formula (X-1): wherein L2 represents a single bond etc., ring W2 represents a C3-C36 saturated hydrocarbon ring in which one —CH2— is replaced by —CO— and in which one or more —CH2— can be replaced by —O— or —CO—, R1 represents a C1-C12 hydrocarbon group, R2 is a C1-C6 alkyl group etc.
    Type: Application
    Filed: November 15, 2010
    Publication date: May 19, 2011
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Koji ICHIKAWA, Masako SUGIHARA, Isao YOSHIDA
  • Publication number: 20110117494
    Abstract: A salt represented by the formula (X): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 and L2 independently each represent a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, ring W1 represents a C3-C36 saturated hydrocarbon ring, R5 is independently in each occurrence a C1-C6 alkyl group or a C1-C6 alkoxy group, w represents an integer of 0 to 2, v represents 1 or 2, Z+ represents an organic counter ion, and W10 represents a group represented by the formula (X-1): wherein ring W2 represents a C3-C36 saturated hydrocarbon ring, R1 represents a C1-C12 hydrocarbon group, R2 is independently in each occurrence a C1-C6 alkyl group or a C1-C6 alkoxy group, and represents an integer of 0 to 2, or a group represented by the formula (X-2): wherein ring W3 represents a C4-C36 lactone ring, R3 is independently in each occurrence a C1-C6 alkyl group, a C1-C6 alkoxy group or a C2-C7 alkoxycarbonyl group a
    Type: Application
    Filed: November 16, 2010
    Publication date: May 19, 2011
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Koji ICHIKAWA, Mitsuyoshi OCHIAI, Masako SUGIHARA
  • Patent number: 7927780
    Abstract: A compound represented by formula (I); and a compound represented by formula (b1-1): wherein X represents —O—, —S—, —O—R3— or —S—R4—, wherein each of R3 and R4 independently represents an alkylene group of 1 to 5 carbon atoms; R2 represents an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, a halogenated alkyl group of 1 to 6 carbon atoms, a halogen atom, a hydroxyalkyl group of 1 to 6 carbon atoms, a hydroxyl group or a cyano group; a represents an integer of 0 to 2; Q1 represents an alkylene group of 1 to 12 carbon atoms or a single bond; Y1 represents an alkylene group of 1 to 4 carbon atoms or a fluorinated alkylene group; M+ represents an alkali metal ion; and A+ represents an organic cation.
    Type: Grant
    Filed: September 10, 2008
    Date of Patent: April 19, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Takeshi Iwai, Hideo Hada, Shinichi Hidesaka, Tsuyoshi Kurosawa, Natsuko Maruyama, Kensuke Matsuzawa, Takehiro Seshimo, Hiroaki Shimizu, Tsuyoshi Nakamura
  • Publication number: 20110045405
    Abstract: Disclosed are a (meth)acrylate compound, a photosensitive polymer, and a resist composition, and the (meth)acrylate compound includes a lactone-group-containing (meth)acrylate compound represented by the following Chemical Formula 1.
    Type: Application
    Filed: August 17, 2010
    Publication date: February 24, 2011
    Inventors: Sung-Jae Lee, Tae-Ho Kim, Jun-Suk Kim, Jin-Young Lee, Kang Ryu, Sang-Jun Choi
  • Publication number: 20110020749
    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: Application
    Filed: July 27, 2010
    Publication date: January 27, 2011
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Koji Ichikawa, Isao Yoshida, Satoshi Yamaguchi
  • Publication number: 20100316952
    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: Application
    Filed: June 9, 2010
    Publication date: December 16, 2010
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Koji Ichikawa, Masako Sugihara, Hiromu Sakamoto
  • Publication number: 20100304294
    Abstract: A salt represented by the formula (I-AA): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C4 perfluoroalkyl group, 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., 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, and a photoresist composition comprising the salt represented by the formula (I-AA) 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: Application
    Filed: May 25, 2010
    Publication date: December 2, 2010
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Koji ICHIKAWA, Masako Sugihara, Tatsuro Masuyama
  • Publication number: 20100304292
    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: Application
    Filed: May 25, 2010
    Publication date: December 2, 2010
    Applicant: SUMITOMO CHEMICAL COMMPANY, LIMITED
    Inventors: Koji ICHIKAWA, Masako Sugihara, Tatsuro Masuyama
  • Publication number: 20100297555
    Abstract: Disclosed is a monomer having an electron-withdrawing substituent and a lactone skeleton, represented by following Formula (1), wherein Ra represents, e.g., a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R1 represents, e.g., a halogen atom or an alkyl or haloalkyl group having 1 to 6 carbon atoms; “A” represents an alkylene group having 1 to 6 carbon atoms, oxygen atom, sulfur atom, or nonbonding; “m” denotes an integer of 0 to 8; Xs each represent an electron-withdrawing substituent; “n” denotes an integer of 1 to 9; and Y represents a bivalent organic group having 1 to 6 carbon atoms. The monomer is useful typically as a monomer component typically for a highly functional polymer, because, when the monomer is applied typically to a resist resin, the resin is satisfactory stable and resistant typically to chemicals, is highly soluble in organic solvents, and has improved hydrolyzability and/or solubility in water after hydrolysis.
    Type: Application
    Filed: February 3, 2009
    Publication date: November 25, 2010
    Inventors: Hiroshi Koyama, Kyuhei Kitao, Akira Eguchi