Sulfur Compound Containing Patents (Class 430/921)

Cross-Reference Art Collections

Sulfur in heterocyclic ring (Class 430/922)
  • Patent number: 7645559
    Abstract: A positive resist composition and method of forming a resist pattern are provided which enable formation of a resist pattern having excellent shape with reduced LWR. The positive resist composition includes a resin component (A) which exhibits increased alkali solubility under action of acid and an acid-generator component (B) which generates acid upon irradiation, the resin component (A) having a structural unit (a1) which has an acetal-type protection group, and the acid-generator component (B) including an acid generator (B1) having a cation moiety represented by general formula (b-5) shown below: wherein Ra and Rb each independently represents an alkyl group, an alkoxy group, a halogen atom or a hydroxyl group; Rc represents an aryl group or alkyl group which may or may not have a substituent; and n? and n? each independently represents an integer of 0 to 3.
    Type: Grant
    Filed: August 16, 2006
    Date of Patent: January 12, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Ryoji Watanabe, Masaru Takeshita
  • Patent number: 7635554
    Abstract: A positive photosensitive composition comprises: (A) a resin that has an acid decomposable repeating unit represented by formula (I) and increases its solubility in an alkali developer by action of an acid: (B) a compound generating an acid upon irradiation with actinic light or radiation; (C) a hydrophobic resin insoluble in an alkali developer and having at least either one of a fluorine atom and a silicon atom; and (D) a solvent, wherein in the formula (I), Xa1 represents a hydrogen atom, an alkyl group, a cyano group or a halogen atom, Ry1 to Ry3 each independently represents an alkyl group or a cycloalkyl group, and at least two of Ry1 to Ry3 may be coupled to form a ring structure, and Z represents a divalent linking group.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: December 22, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Toshiaki Fukuhara, Shinichi Kanna, Hiromi Kanda
  • Patent number: 7629106
    Abstract: There is disclosed a resist composition which shows high sensitivity and high resolution on exposure to high energy beam, provides reduced Line Edge Roughness because swelling at the time of development is reduced, provides minor amounts of residue after development, has excellent dry etching resistance, and can also be used suitably for the liquid immersion lithography; and a patterning process using the resist composition. There can be provided a resist composition which comprises, at least, a polymer including repeating units represented by the following general formulae (a) and (b).
    Type: Grant
    Filed: October 16, 2006
    Date of Patent: December 8, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Youichi Ohsawa, Seiichiro Tachibana
  • Patent number: 7625687
    Abstract: This invention pertains to a silsesquioxane resin with improved lithographic properties (such as etch-resistance, transparency, resolution, sensitivity, focus latitude, line edge roughness, and adhesion) suitable as a photoresist; a method for in-corporating the fluorinated or non-fluorinated functional groups onto silsesquioxane backbone. The silsesquioxane resins of this invention has the general structure (HSiO3/2)a(RSiO3/2)b wherein; R is an acid dissociable group, a has a value of 0.2 to 0.9 and b has a value of 0.1 to 0.8 and 0.9?a+b?1.0.
    Type: Grant
    Filed: June 30, 2004
    Date of Patent: December 1, 2009
    Assignee: Dow Corning Corporation
    Inventors: Sanlin Hu, Eric Scott Moyer, Sheng Wang, David Lee Wyman
  • Patent number: 7618765
    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 which is a specific sulfonium salt compound. The resin (A) is a polymer comprising tertiary alkyl protective group units having a hydrophobic tetracyclo[4.4.0.12,5.17,10]dodecane structure, di- or trihydroxyadamantyl units, and monocyclic lactone units.
    Type: Grant
    Filed: January 2, 2008
    Date of Patent: November 17, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Seiichiro Tachibana, Katsuhiro Kobayashi
  • Patent number: 7615330
    Abstract: A positive resist composition containing a compound including a sulfonium cation having a structure represented by the formula (Z-I) as defined herein, a low molecular weight compound which increases solubility in an alkali developing solution by an action of an acid, and a compound which generates a compound having a structure represented by the formula (A-I) as defined herein upon irradiation of an actinic ray or a radiation.
    Type: Grant
    Filed: March 26, 2007
    Date of Patent: November 10, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Sou Kamimura, Tomoya Sasaki, Yasutomo Kawanishi, Kenji Wada
  • Patent number: 7611822
    Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, T represents a methylene group or a carbonyl group, R represents an adamantyl group substituted with at least one selected from the group consisting of a C1-C4 alkyl group, a C1-C4 alkoxy group, a hydroxyl group, a hydroxymethyl group, a cyano group and an oxo group, and A+ represents an organic counter ion. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).
    Type: Grant
    Filed: July 22, 2008
    Date of Patent: November 3, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Ichiki Takemoto
  • Patent number: 7579132
    Abstract: The present invention provides a salt represented by the formula (I): wherein X represents an n-valent connecting group, Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, n represents 2 or 3, and A+ represents an organic counter ion. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).
    Type: Grant
    Filed: June 4, 2007
    Date of Patent: August 25, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukako Harada, Isao Yoshida, Satoshi Yamaguchi
  • Patent number: 7575850
    Abstract: The present invention provides a chemically amplified resist composition comprising: a resin which comprises a structural unit having an acid-labile group and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X represents a C3-C30 cyclic hydrocarbon group in which one —CH2— is substituted with —COO—, and at least one hydrogen atom in the C3-C30 cyclic hydrocarbon group may be substituted, and p represents an integer of 1 to 4, and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, and at least two salts selected from a salt represented by the formula (II): wherein Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, A+ represents an organic counter ion and R21 represents a C1-C30 hydrocarbon group which may be substituted and at least one —CH2— in the C1-C30 hydrocarbon group may be substituted with —CO
    Type: Grant
    Filed: January 28, 2008
    Date of Patent: August 18, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiyuki Takata, Satoshi Yamamoto, Satoshi Yamaguchi
  • Patent number: 7572570
    Abstract: The present invention provides a chemically amplified resist composition comprising: (A) a resin which comprises (a) a structural unit having an acid-labile group, (b) a structural unit having at least one hydroxyl group, (c) a structural unit having at least one lactone structure, and (d) a structural unit represented by the formula (Ia) or (Ib): wherein R1 represents a hydrogen atom or a methyl group, R3 represents a methyl group, n represents an integer of 0 to 14, and Z represents a single bond or —[CH2]k—COO—, and (B) at least one acid generator.
    Type: Grant
    Filed: March 20, 2008
    Date of Patent: August 11, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yusuke Fuji, Yoshiyuki Takata
  • Patent number: 7569326
    Abstract: A sulfonium salt having a polymerizable anion generates a strong sulfonic acid upon exposure to high-energy radiation so that it facilitates effective scission of acid labile groups in chemically amplified resist compositions. It is useful as a monomer from which a base resin for use in radiation-sensitive resist compositions is derived.
    Type: Grant
    Filed: October 25, 2007
    Date of Patent: August 4, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama, Takeru Watanabe
  • Patent number: 7560219
    Abstract: Sulfonium salt photoinitiator compositions, precursors useful in the preparation of such photoinitiators and the use of these photoinitiators in, e.g., UV curable adhesives, UV curable sealants, UV curable coating compositions, such as printing inks and varnishes, and UV curable encapsulants.
    Type: Grant
    Filed: April 26, 2007
    Date of Patent: July 14, 2009
    Assignee: Henkel AG & Co. KGaA
    Inventors: Yuxia Liu, Donald E. Herr
  • Patent number: 7560221
    Abstract: Lithographic printing plate precursor comprising: a) an untreated or pretreated substrate and b) a radiation-sensitive coating comprising: (i) at least one polymeric binder soluble or swellable in aqueous alkaline developers; (ii) at least one free-radical polymerizable monomer and/or oligomer comprising at least one non-aromatic C—C double bond and at least one SH group in the molecule; and (iii) a radiation-sensitive initiator or initiator system for free-radical polymerization, wherein component (ii) has the formula (I) wherein each R1a, R1b and R1c is independently selected from H, C1-C6 alkyl, C2-C8 alkenyl, aryl, halogen, CN and COOR1d, wherein R1d is H, C1-C18 alkyl, C2-C8 alkenyl, C2-C8 alkynyl or aryl; and Z is an aliphatic, heterocyclic or heteroaromatic spacer or a combination of two or more thereof, wherein Z can optionally comprise one or more additional SH groups and/or one or more additional non-aromatic C—C double bonds; and each Z1 is independently selected from a single bond, formulae (Ia),
    Type: Grant
    Filed: January 19, 2005
    Date of Patent: July 14, 2009
    Assignee: Kodak Graphic Communications GmbH
    Inventors: Hans-Joachim Timpe, Ursula Muller
  • Patent number: 7556908
    Abstract: The present invention provides a chemically amplified positive resist composition comprising (A) a resin which comprises (i) a structural unit of the formula (I) and (ii) at least one structural unit selected from the group consisting of structural units of the formulas (II), (O/II), (IV) and (V) and (B) an acid generator. The present invention further provides a novel monomers useful for the resist composition, and process for the monomers and the compositions.
    Type: Grant
    Filed: April 21, 2005
    Date of Patent: July 7, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ichiki Takemoto, Isao Yoshida, Takayuki Miyagawa
  • Patent number: 7547501
    Abstract: The present application relates to photoactive materials having the formula wherein C1+ is a cation; each of R30, R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, and R41 are selected from hydrogen, alkyl, alkyl chain optionally containing one or more O atoms, halide, aryl, aralkyl, alkoxyalkyl, cycloalkyl, hydroxyl, and alkoxy, the alkyl, alkyl chain optionally containing one or more O atoms, aryl, aralkyl, alkoxyalkyl, cycloalkyl, and alkoxy groups being unsubstituted or substituted.
    Type: Grant
    Filed: October 5, 2006
    Date of Patent: June 16, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Ralph R. Dammel, M. Dalil Rahman, David L. Rentkiewicz, Karl van Werden
  • Patent number: 7531290
    Abstract: Sulfonate salts have the formula: R1SO3—CH(Rf)—CF2SO3?M+ wherein R1 is alkyl or aryl, Rf is H or trifluoromethyl, and M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: October 27, 2006
    Date of Patent: May 12, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
  • Patent number: 7527912
    Abstract: Photoacid generators generate sulfonic acids of formula (1a) upon exposure to high-energy radiation. RC(?O)R1—COOCH(CF3)CF2SO3?H+??(1a) R is hydroxyl, alkyl, aryl, hetero-aryl, alkoxy, aryloxy or hetero-aryloxy, R1 is a divalent organic group which may have a heteroatom (O, N or S) containing substituent, or R1 may form a cyclic structure with R. 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: September 27, 2007
    Date of Patent: May 5, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Koji Hasegawa, Masaki Ohashi
  • Patent number: 7527911
    Abstract: A photosensitive composition, which comprises (A) a compound capable of generating an organic acid represented by formula (I) upon irradiation with actinic ray or radiation: wherein Z represents a monovalent organic group, when two Z's are present, the two Z's may be the same or different, and they may be bonded to each other to form a cyclic structure; X represents —CO— or —SO2—, when two X's are present, the two X's may be the same or different; R represents a monovalent organic group, when two R's are present, the two R's may be the same or different, and they may be bonded to each other to form a cyclic structure; Z and R may be bonded to each other to form a cyclic structure; and n represents an integer of 1 or 2; and the compound capable of generating the organic acid represented by formula (I).
    Type: Grant
    Filed: February 20, 2007
    Date of Patent: May 5, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Kenji Wada
  • Patent number: 7527910
    Abstract: The present invention provides a salt of the formula (I): wherein X represents alkylene group or substituted alkylene group; Q1 and Q2 each independently represent fluorine atom or perfluoroalkyl group having 1 to 6 carbon atoms; A+ represents organic counter ion; and n shows 0 or 1. The present invention also provides a chemically amplified resist composition comprising the salt of the formula (I), and a resin which contains a structural unit having an acid-labile group and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid.
    Type: Grant
    Filed: December 26, 2006
    Date of Patent: May 5, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamaguchi, Isao Yoshida, Yukako Harada
  • Patent number: 7527913
    Abstract: A photoresist composition includes about 4% to about 10% by weight of a photoresist resin, about 0.1% to about 0.5% by weight of a photoacid generator having a sulfonium-salt cationic group and a sulfonium-salt anionic group containing a carboxyl group as a hydrophilic site and a remainder of a solvent. The photoresist composition may form a photoresist pattern having a uniform profile.
    Type: Grant
    Filed: January 24, 2008
    Date of Patent: May 5, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Young-Gil Kwon, Young-Ho Kim, Do-Young Kim, Jae-Hee Choi, Se-Kyung Baek
  • Patent number: 7524609
    Abstract: A photosensitive composition, which comprises (A) a compound capable of generating an organic acid represented by formula (I) upon irradiation with actinic ray or radiation: Z—A—X—B—R—(Y)n??(I) wherein Z represents an organic acid group; A represents a divalent linking group; X represents a divalent linking group having a hetero atom; B represents an oxygen atom or —N(Rx)—; Rx represents a hydrogen atom or a monovalent organic group; R represents a monovalent organic group substituted with Y, and when B represents —N(Rx)—, R and Rx may be bonded to each other to form a cyclic structure; Y represents —COOH or —CHO, and when a plurality of Y's are present, the plurality of Y's may be the same or different; and n represents an integer of from 1 to 3.
    Type: Grant
    Filed: March 9, 2007
    Date of Patent: April 28, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Kenji Wada
  • Patent number: 7521168
    Abstract: A resist composition for an electron beam, EUV or X-ray comprising (A1) a compound that has a reduction potential higher than that of diphenyl iodonium salt and generates an acid upon irradiation of an actinic ray or radiation.
    Type: Grant
    Filed: February 11, 2003
    Date of Patent: April 21, 2009
    Assignee: Fujifilm Corporation
    Inventors: Kazuyoshi Mizutani, Hyou Takahashi
  • Patent number: 7514202
    Abstract: A thermal acid generator of generating an acid on heating above 100° C. has formula: CF3CH(OCOR)CF2SO3?(R1)4N+ wherein R is alkyl or aryl, R1 is hydrogen, alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl, or R1 may bond together to form a ring with N. The sulfonic acid generated possesses an ester site within molecule so that less bulky acyl groups to bulky groups may be incorporated therein. The thermal acid generator provides a sufficient acid strength, is less volatile due to a high molecular weight, and ensures film formation. Upon disposal of used resist liquid, it may be converted into low accumulative compounds.
    Type: Grant
    Filed: May 9, 2007
    Date of Patent: April 7, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Jun Hatakeyama
  • Patent number: 7510816
    Abstract: A resist composition is provided comprising a polysiloxane, a specific acid generator, a nitrogen-containing organic compound, and a solvent. The resist composition exerts high-resolution performance without the problem of a T-top profile and is suited for the bilayer resist process using ArF exposure.
    Type: Grant
    Filed: October 4, 2005
    Date of Patent: March 31, 2009
    Assignee: Shin-Estu Chemical Co., Ltd.
    Inventors: Katsuya Takemura, Kazumi Noda, Youichi Ohsawa
  • Patent number: 7511169
    Abstract: Sulfonate salts have the formula: CF3—CH(OCOR)—CF2SO3?M+ wherein R is C1-C20 alkyl or C6-C14 aryl, and M+ is a lithium, sodium, potassium, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: April 5, 2006
    Date of Patent: March 31, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
  • Patent number: 7510822
    Abstract: A stimulation sensitive composition comprising: (A) a compound represented by the specific formula which is capable of generating an acid or a radical by stimulation from the external.
    Type: Grant
    Filed: April 9, 2003
    Date of Patent: March 31, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7501222
    Abstract: A polymer including a monomer represented by the following Formula and a photoresist composition including the same are disclosed. The polymer and photoresist composition can improve the resolution and the process margin due to the low activation energy of the deprotection reaction of the alcohol ester group including saturated cyclic hydrocarbyl group, and also can produce fine photoresist patterns because they have a stable PEB(Post Exposure Baking) temperature sensitivity, and further, can improve the focus depth margin and the line edge roughness of the resist layer. In the above Formula, R* is a hydrogen or methyl group, R1 is saturated hydrocarbyl group of 1 to 5 carbon atoms, R is mono-cyclic or multi-cyclic homo or hetero saturated hydrocarbyl group of 3 to 50 carbon atoms, and n is an integer of at least 2.
    Type: Grant
    Filed: June 21, 2006
    Date of Patent: March 10, 2009
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jung-Youl Lee, Jae-Woo Lee, Jae-Hyun Kim
  • Patent number: 7498126
    Abstract: A photoacid generator has formula (1). A chemically amplified resist composition comprising the photoacid generator has advantages including a high resolution, focus latitude, long-term PED dimensional stability, and a satisfactory pattern profile shape. When the photoacid generator is combined with a resin having acid labile groups other than those of the acetal type, resolution and top loss are improved. The composition is suited for deep UV lithography.
    Type: Grant
    Filed: June 5, 2007
    Date of Patent: March 3, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Kazunori Maeda, Satoshi Watanabe
  • Patent number: 7491482
    Abstract: The present application relates to a compound of formula AiXi where Ai is an organic onium cation; and Xi is an anion of the formula X—CF2CF2OCF2CF2—SO3?. The compounds are useful as photoactive materials.
    Type: Grant
    Filed: December 4, 2006
    Date of Patent: February 17, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Munirathna Padmanaban, Srinivasan Chakrapani, M. Dalil Rahman
  • Patent number: 7491484
    Abstract: In a photoresist composition and a method of forming a pattern using the same, the photoresist composition includes about 0.1 to about 0.5 percent by weight of a photoacid generator including a positively charged sulfonium ion and a negatively charged sulfonate ion having a hydrophilic carboxylic group, about 4 to about 10 percent by weight of a resin, and a solvent.
    Type: Grant
    Filed: October 10, 2007
    Date of Patent: February 17, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Young-Gil Kwon, Do-Young Kim, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim
  • Patent number: 7485407
    Abstract: Disclosed are a siloxane compound, a photoresist composition using the same, and a method of forming a pattern, wherein the siloxane compound is having a general formula: wherein R1 is a tertiary butyl group or a 1-(tert-butoxy)ethyl group, and R2 and R3 is each independently a lower alkyl group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: December 18, 2006
    Date of Patent: February 3, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim, Do-Young Kim
  • Patent number: 7482107
    Abstract: Photoresist compositions having a resin binder with an acid labile blocking group with an activation energy in excess of 20 Kcal/mol. for deblocking, a photoacid generator capable of generating a halogenated sulfonic acid upon photolysis and optionally, a base.
    Type: Grant
    Filed: March 23, 2006
    Date of Patent: January 27, 2009
    Assignee: Shipley Company, L.L.C.
    Inventors: James W. Thackeray, James F. Cameron, Roger F. Sinta
  • Patent number: 7465528
    Abstract: A positive-working photosensitive composition that includes (A) a resin containing repeating units having diamantane structures and capable of decomposing under action of an acid to increase solubility in an alkali developer, (B) a compound capable of generating a specific organic acid upon irradiation with an actinic ray or radiation, and (C) a solvent.
    Type: Grant
    Filed: October 17, 2006
    Date of Patent: December 16, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Fumiyuki Nishiyama, Kunihiko Kodama
  • Patent number: 7465527
    Abstract: The resist material contains a photo-acid generator having an absorption peak to exposure light having a wavelength of less than 300 nm, and a second photo-acid generator having an absorption peak to exposure light having a wavelength of 300 nm or more. The method for forming a resist pattern comprises a step for selectively exposing which exposes a coating film of the resist material to an exposure light having a wavelength of less than 300 nm, and a step for selectively exposing by using an exposure light having a wavelength of 300 nm or more. The semiconductor device comprises a pattern formed by the resist pattern. The method for forming a semiconductor device comprises a step for forming a resist pattern on an underlying layer by the aforementioned manufacturing method, and a step for patterning the underlying layer by etching using the resist pattern as a mask.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: December 16, 2008
    Assignee: Fujitsu Limited
    Inventors: Junichi Kon, Ei Yano
  • Patent number: 7459261
    Abstract: There is disclosed a resist composition which comprises, at least, a polymer in which a sulfonium salt having a polymerizable unsaturated bond, a (meth)acrylate having a lactone or a hydroxyl group as an adhesion group, and a (meth)acrylate having an ester substituted with an acid labile group are copolymerized. There can be provided a resist composition with high resolution which has high sensitivity and high resolution to high energy beam, especially to ArF excimer laser, F2 excimer laser, EUV, X-ray, EB, etc., has reduced line edge roughness, and comprises a polymeric acid generator which has insolubility in water, and sufficient thermal stability and preservation stability.
    Type: Grant
    Filed: December 19, 2005
    Date of Patent: December 2, 2008
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Youichi Ohsawa, Seiichiro Tachibana
  • Patent number: 7449573
    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: February 14, 2005
    Date of Patent: November 11, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Kenji Wada, Kaoru Iwato
  • Patent number: 7439006
    Abstract: A salt represented by the formula (I): wherein X represents a C1-C12 divalent linear or branched chain hydrocarbon group, Y represents a C1-C30 hydrocarbon group which may be substituted with at least one substituent, and at least one —CH2— in the C1-C30 hydrocarbon group may be substituted with —O— or —CO—, Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, and A+ represents an organic counter ion. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).
    Type: Grant
    Filed: August 10, 2007
    Date of Patent: October 21, 2008
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Isao Yoshida, Yukako Harada, Takayuki Miyagawa
  • Patent number: 7435526
    Abstract: A positive photosensitive composition comprises a compound capable of generating a specified sulfonic acid upon irradiation with one of an actinic ray and radiation and (B) a resin capable of decomposing under the action of an acid to increase the solubility in an alkali developer.
    Type: Grant
    Filed: June 14, 2004
    Date of Patent: October 14, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Toshiaki Aoai
  • Patent number: 7422839
    Abstract: The use of a positive resist composition that includes a resin with a specific structure improves the resolution and yields a resist pattern with a favorable shape. In addition, when a resist layer is formed on either a magnetic film or a metallic oxidation prevention film formed on the magnetic film, the layer is less prone to tailing and undercutting phenomena.
    Type: Grant
    Filed: July 5, 2004
    Date of Patent: September 9, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Hiroshi Shimbori
  • Patent number: 7419760
    Abstract: Disclosed herein is a top anti-reflective coating composition comprising a bissulfone compound, as a photoacid generator, represented by Formula 1 below: wherein R1 and R2 are independently, a straight, branched or cyclic alkyl, aryl, alkenyl, oxoalkyl or oxoaryl group of 1 to 20 carbon atoms; or a halogen-substituted straight, branched or cyclic alkyl, aryl, alkenyl, oxoalkyl or oxoaryl group of 1 to 20 carbon atoms. Since the top anti-reflective coating composition dissolves a portion of a photoacid generator present at the top of an underlying photosensitizer, particularly, upon formation of a top anti-reflective coating, it can prevent the top from being formed into a thick section. Therefore, the use of the anti-reflective coating composition enables the formation of a vertical pattern of a semiconductor device.
    Type: Grant
    Filed: June 22, 2005
    Date of Patent: September 2, 2008
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Cheol Kyu Bok, Sam Young Kim, Chang Moon Lim, Seung Chan Moon
  • Patent number: 7396899
    Abstract: The present invention provides a sulfonium salt of the formula (Ia) a polymeric compound comprising a structural unit of the formula (Ib) and a chemical amplification type positive resist composition comprising (A) an acid generator comprising at least one compound selected from the group consisting of a sulfonium salt of the formula (Ia), a polymeric compound comprising a structural unit of the formula (Ib), and a sulfonium salt of the formula (Ic); and (B) resin which contains a structural unit having an acid labile group and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid.
    Type: Grant
    Filed: December 22, 2006
    Date of Patent: July 8, 2008
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Airi Yamada, Yasunori Uetani, Akira Kamabuchi
  • Patent number: 7396633
    Abstract: With the damascene process in which an interconnection is formed using a conventional chemically amplified positive photoresist composition, there arises a problem that the photoresist within the via hole (as well as in its vicinity) may remain even after the exposure and the development are carried out. The present invention relates to a chemically amplified resist composition comprising, at least, a photo acid generator, a quencher and a salt having a buffering function for an acid which is generated from the acid generator by irradiation, wherein the salt having the buffering function for the acid generated from the acid generator is a salt derived from a long chain alkylbenzenesulfonic acid or a long chain alkoxybenzenesulfonic acid and an organic amine that is a basic compound.
    Type: Grant
    Filed: June 23, 2004
    Date of Patent: July 8, 2008
    Assignees: NEC Electronics Corporation, Shin-Etsu Chemical Co., Ltd.
    Inventors: Seiji Nagahara, Satoshi Watanabe, Kazunori Maeda
  • Patent number: 7393627
    Abstract: Novel classes of ionic photoacid generator (PAGs) compounds having relatively environmentally friendly anions with no perfluorooctyl sulfonate (no-PFOS) are provided and photoresist composition that comprise such compounds. The new PAGs produce a photoacid having a short or no perfluoro alkyl chain (ie., no-PFOS) attached to a variety of functional groups. The PAGs of the invention are useful as photoactive component in the chemically amplified resist compositions used for microfabrication.
    Type: Grant
    Filed: March 16, 2005
    Date of Patent: July 1, 2008
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Ramakrishnan Ayothi, Kyung-Min Kim, Xiang-Qian Liu
  • Patent number: 7390613
    Abstract: The present application relates to a compound of formula Ai Xi Bi where Ai and Bi are each individually an organic onium cation; and Xi is anion of the formula ?O3S—CF2CF2OCF2CF2—SO3?. The compounds are useful as photoactive materials.
    Type: Grant
    Filed: December 4, 2006
    Date of Patent: June 24, 2008
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: M. Dalil Rahman, David L. Rentkiewicz
  • Patent number: 7387865
    Abstract: A composition containing a photoacid generator monomer and surfactant, and a method for synthesizing a compound on a substrate using the composition are provided. The method includes bonding a layer of first molecules having an acid labile protecting group to a solid substrate; coating a layer of the photoacid generator monomer composition according to the present invention on the layer of first molecules; exposing the composition layer to light and then heat-treating to remove the acid labile protecting group from the first molecules corresponding to the exposed portion; washing and removing the composition layer from the exposed and unexposed portions; and bonding second molecules to the exposed first molecules.
    Type: Grant
    Filed: July 20, 2004
    Date of Patent: June 17, 2008
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sung-ouk Jung, Seung-ju Seo, Jae-chan Park
  • Patent number: 7368224
    Abstract: The invention provides a photopolymerizable composition having a high photosensitivity, which comprises a metal complex of a squarylium compound, a radical generator, and a compound having at least one ethylenically unsaturated double bond. The photopolymerizable composition of the present invention is advantageously used for a visible laser recording material such as a PS (Presensitized Plate) for laser direct plate-making, a dry film resist, a digital proof, a hologram, or the like, a panchromatic sensitive material (e.g., a sensitive material for a color hologram and a sensitive material used for full-color display and containing a photopolymerizable composition in a microcapsule), paints, adhesives, and so on.
    Type: Grant
    Filed: April 3, 2003
    Date of Patent: May 6, 2008
    Assignee: Kyowa Hakko Chemical Co., Ltd.
    Inventors: Tsuguo Yamaoka, Ikuo Shimizu, Hiroshi Toyoda, Motoharu Kinugasa, Masanori Ikuta, Kyoko Katagi
  • Patent number: 7361446
    Abstract: A positive resist composition comprising (a) a resin that is decomposed by the action of an acid to increase solubility in an alkali developing solution, contains a structural unit having a group represented by formula (X) defined in the specification, has a weight average molecular weight of not more than 5,000, and contains an acid decomposable group in an amount of not more than 40% based on the sum total of a number of the acid decomposable group and a number of an alkali-soluble group not protected with the acid decomposable group, and (b) a compound that generates an acid upon irradiation of an actinic ray or radiation.
    Type: Grant
    Filed: March 30, 2004
    Date of Patent: April 22, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Koji Shirakawa, Toru Fujimori, Shoichiro Yasunami
  • Patent number: 7358028
    Abstract: The present invention provides a chemical amplification type positive photoresist composition which is excellent in storage stability as a resist solution in a bottle. A novolak resin or a hydroxystyrenic resin is reacted with a crosslinking agent to give a slightly alkali-soluble or alkali-insoluble resin having such a property that solubility in an aqueous alkali solution is enhanced in the presence of an acid, which is then dissolved in an organic solvent, together with (B) a compound generating an acid under irradiation with radiation to obtain a chemical amplification type positive photoresist composition wherein the content of an acid component is 10 ppm or less.
    Type: Grant
    Filed: May 19, 2004
    Date of Patent: April 15, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kenji Maruyama, Masaki Kurihara, Ken Miyagi, Satoshi Niikura, Satoshi Shimatani, Masahiro Masujima, Kazuyuki Nitta, Toshihiro Yamaguchi, Kousuke Doi
  • Patent number: 7351515
    Abstract: A positive resist composition includes: (A) a resin capable of increasing a solubility thereof in an alkali developer by an action of an acid; (B) a compound capable of generating a sulfonic acid represented by the following formula (I) upon irradiation with one of an actinic ray and a radiation; and (C1) at least one of an amine compound having at least an aliphatic hydroxyl group in a molecule and an amine compound having at least an ether bond in a molecule: A1A2-SO3H)n ??(I) wherein A1 represents an n-valent linking group, A2 represents a single bond or a divalent aliphatic group, and A2's each may be the same or different, provided that at least one group represented by A1 or A2 contains a fluorine atom, and n represents an integer of from 2 to 4.
    Type: Grant
    Filed: September 16, 2004
    Date of Patent: April 1, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Shoichiro Yasunami, Kenji Wada, Kunihiko Kodama, Kenichiro Sato
  • Patent number: RE40964
    Abstract: A negative type resist composition is provided, which provides excellent resolution, satisfactory profile and outstanding process stability; is suitable for exposure using deep ultra violet ray; and comprises alkali soluble resin, acid generator, crosslinking agent, and a basic compound represented by the following formula (I) wherein, A represents sulfide group, disulfide group or bivalent aliphatic hydrocarbon residue which may be optionally interrupted by imino group, sulfide group, or disulfide group, X represents nitrogen atom or C(NH2), and R1 and R2 independently represent hydrogen or alkyl.
    Type: Grant
    Filed: September 17, 2003
    Date of Patent: November 10, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masumi Suetsugu, Takehiro Kusumoto, Naoki Takeyama, Masanori Shinada