Sulfur Compound Containing Patents (Class 430/921)
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Patent number: 8609889Abstract: The photoacid generator produces a sulfonic acid which has a bulky cyclic structure in the sulfonate moiety and a straight-chain hydrocarbon group and thus shows a controlled acid diffusion behavior and an adequate mobility. The PAG is fully compatible with a resin to form a resist composition which performs well during the device fabrication process and solves the problems of resolution, LWR, and exposure latitude.Type: GrantFiled: July 1, 2010Date of Patent: December 17, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
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Patent number: 8597869Abstract: A sulfonium salt of a naphthyltetrahydrothiophenium cation having a fluoroalkoxy chain with a specific anion is provided. The sulfonium salt is used as a photoacid generator to form a resist composition which when processed by immersion lithography, offers advantages of restrained dissolution in the immersion water and less pattern dependence or dark/bright bias.Type: GrantFiled: September 23, 2011Date of Patent: December 3, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayoshi Sagehashi, Youichi Ohsawa, Koji Hasegawa, Takeshi Kinsho, Tomohiro Kobayashi
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Patent number: 8592128Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes: (A) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (B) a resin capable of increasing a dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure; and (D) a low molecular compound having a group capable of leaving by an action of an acid, and a pattern forming method uses the composition.Type: GrantFiled: January 15, 2010Date of Patent: November 26, 2013Assignee: FUJIFILM CorporationInventor: Shuhei Yamaguchi
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Patent number: 8592132Abstract: A resist composition includes (A1) a resin having a structural unit represented by the formula (I), (A2) a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and (B) an acid generator having an acid-labile group. wherein R1 represents a hydrogen atom or a methyl group; A1 represents a C1 to C6 alkanediyl group; R2 represents a C1 to C10 hydrocarbon group having a fluorine atom.Type: GrantFiled: February 24, 2012Date of Patent: November 26, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Satoshi Yamaguchi, Yuki Suzuki
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Patent number: 8586281Abstract: A positive resist composition including: a base component; and a sensitizer which a polymeric compound having a core portion that includes a hydrocarbon group or a heterocycle of two or more valences and at least one arm portion bonded to the core portion and represented by formula (1), and a polymeric compound having a core portion including a polymer having a molecular weight of 500 to 20,000 and at least one arm portion bonded to the core portion and represented by formula (1); and either the base component includes a resin component that generates acid upon exposure and exhibits increased solubility in an alkali developing solution under action of acid, or the positive resist composition further contains an acid generator component including a compound that generates acid upon exposure: —(X)—Y??(1) in which X represents a divalent linking group having an acid dissociable group; and Y represents a polymer chain.Type: GrantFiled: June 8, 2011Date of Patent: November 19, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Jun Iwashita, Masahito Yahagi, Kenri Konno, Isamu Takagi
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Patent number: 8580486Abstract: There is provided an acid having a fluorine-containing carbanion structure or a salt having a fluorine-containing carbanion structure, which is represented by the following general formula (1). By using a photoacid generator for chemically amplified resist materials that generates this acid, it is possible to provide a photoacid generator which has a high sensitivity to the ArF excimer laser light or the like, of which acid (photo generated acid) to be generated has a sufficiently high acidity, and which has a high dissolution in resist solvent and a superior compatibility with resin, and a resist material containing such a photoacid generator.Type: GrantFiled: March 10, 2009Date of Patent: November 12, 2013Assignee: Central Glass Company, LimitedInventors: Masashi Nagamori, Satoru Narizuka, Susumu Inoue, Takashi Kume
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Patent number: 8574812Abstract: A resist composition of the invention includes: (A1) a resin having a structural unit represented by the formula (I), (A2) a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and (B) an acid generator represented by the formula (II), wherein R1, A1, R2, Q1, Q2, L1, ring W1, and Z+ are defined in the specification.Type: GrantFiled: February 24, 2012Date of Patent: November 5, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Satoshi Yamaguchi
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Patent number: 8574817Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1), (2) or (3) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a reduced acid diffusion rate, and forms a pattern with good profile, minimal edge roughness, and etch resistance. In formula (1), R1, R2, R5, R6, R8, and R9 are alkyl, aryl, or alkenyl, R3, R4, R7, R10, and R11 are hydrogen, alkyl, alkoxy, acyloxy, halogen, cyano, nitro, hydroxyl or trifluoromethyl, M is methylene or ethylene, R is a single bond or linking group.Type: GrantFiled: September 13, 2012Date of Patent: November 5, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Koji Hasegawa
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Patent number: 8557499Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes a compound (A) that when exposed to actinic rays or radiation, generates any of the acids of general formula (II) below and a resin (B) whose rate of dissolution into an alkali developer is increased by the action of an acid. (The characters used in general formula (I) have the meanings mentioned in the description.Type: GrantFiled: July 8, 2010Date of Patent: October 15, 2013Assignee: FUJIFILM CorporationInventors: Shuhei Yamaguchi, Akinori Shibuya, Shohei Kataoka
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Patent number: 8557500Abstract: 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: GrantFiled: February 28, 2012Date of Patent: October 15, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Hiromu Sakamoto, Takahiro Yasue
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Patent number: 8546061Abstract: A photo-curing polysiloxane composition includes a polysiloxane, an o-naphthoquinonediazidesulfonate compound, and a solvent. The polysiloxane contains 25 wt % to 60 wt % of a polysiloxane fraction having a molecular weight ranging from 10,000 to 80,000 based on a total weight of the polysiloxane when calculated from an integral molecular weight distribution curve obtained by plotting cumulative weight percentage versus molecular weight falling within a range between 400 and 100,000 measured by gel permeation chromatography. The amount of oligomers in the polysiloxane having a molecular weight less than 800 is from 0 wt % to 10 wt % based on a total weight of the photo-curing polysiloxane composition. A protective film formed from the photo-curing polysiloxane composition and an element containing the protective film are also disclosed.Type: GrantFiled: November 8, 2011Date of Patent: October 1, 2013Assignee: Chi Mei CorporationInventors: Ming-Ju Wu, Chun-An Shih
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Patent number: 8546059Abstract: The present invention provides a photoresist composition comprising a resin, an acid generator and a compound represented by the formula (C1): wherein Rc1 represents an aromatic group which can have one or more substituents, Rc2 and Rc3 independently each represent a hydrogen atom, an aliphatic hydrocarbon group which can have one or more substituents or an aromatic group which can have one or more substituents, Rc4 and Rc6 independently each represent a hydrogen atom or an aliphatic hydrocarbon group which can have one or more substituents, or Rc4 and Rc6 are bonded each other to form an alkanediyl group, Rc5 represents an aliphatic hydrocarbon group which can have one or more substituents or an amino group which can have one or two substituents, Rc7 represents a hydrogen atom or an aliphatic hydrocarbon group which can have one or more substituents, or Rc5 and Rc7 are bonded each other to form an alkanediyl group.Type: GrantFiled: November 24, 2010Date of Patent: October 1, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Takayuki Miyagawa, Mitsuhiro Hata
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Patent number: 8546060Abstract: A chemically amplified positive resist composition is provided comprising a polymer PB having an amine structure bound thereto and a polymer PA comprising recurring units having an acidic side chain protected with an acid labile protective group and recurring units having an acid generating moiety on a side chain.Type: GrantFiled: February 15, 2011Date of Patent: October 1, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Keiichi Masunaga, Satoshi Watanabe, Akinobu Tanaka, Daisuke Domon
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Resist composition, method of forming resist pattern, compound and acid generator including the same
Patent number: 8541157Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under the action of acid and an acid-generator component (B) which generates acid upon exposure, wherein the acid-generator component (B) includes an acid generator (B1) composed of a compound having a base dissociable group within a cation moiety.Type: GrantFiled: September 25, 2009Date of Patent: September 24, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Sho Abe -
Patent number: 8541161Abstract: Provided are an actinic ray-sensitive or radiation-sensitive resin composition; a resist film using the composition; and a pattern forming method. The actinic ray-sensitive or radiation-sensitive resin composition includes (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, the resin containing a repeating unit represented by formula (I), a repeating unit represented by formula (II) and a repeating unit represented by formula (III), and (B) a compound capable of generating a fluorine atom-containing acid upon irradiation with an actinic ray or radiation: wherein each of R1 and R11 independently represents a hydrogen atom or an alkyl group which may have a substituent, and R12 represents a phenyl group which may have a substituent.Type: GrantFiled: March 23, 2010Date of Patent: September 24, 2013Assignee: FUJIFILM CorporationInventors: Kana Fujii, Shuji Hirano, Shinki Yamada, Toru Fujimori
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Patent number: 8530137Abstract: The present invention provides a photoresist composition having a sulfonium salt comprising an anion represented by the formula (IA): wherein R1 and R2 independently represent a hydrogen atom, a C1-C12 aliphatic hydrocarbon group, a C3-C20 saturated cyclic hydrocarbon group, a C6-C20 aromatic hydrocarbon group or a C7-C21 aralkyl group, and the aliphatic hydrocarbon group, the saturated cyclic hydrocarbon group, the aromatic hydrocarbon group and the aralkyl group can have one or more substituents selected from the group consisting of a hydroxyl group, a cyano group, a fluorine atom, a trifluoromethyl group and a nitro group, and one or more —CH2— in the aliphatic hydrocarbon group can be replaced by —O— or —CO—, or R1 and R2 are bonded each other to form a C4-C20 nitrogen-containing ring together with the nitrogen atom to which they are bonded, an acrylic resin having an acid-labile group and being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solutioType: GrantFiled: February 11, 2011Date of Patent: September 10, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuro Masuyama, Satoshi Yamaguchi
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Patent number: 8530135Abstract: The present invention provides a photoresist composition comprising a resin 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, an acid generator and a compound represented by the formula (I): wherein Z1 represents a C7-C20 alkylene group, a C3-C20 divalent saturated cyclic group or a divalent group formed by combining at least one C1-C6 alkylene group with at least one C3-C20 divalent saturated cyclic group.Type: GrantFiled: September 22, 2010Date of Patent: September 10, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Soon Shin Kim, Isao Yoshida, Koji Ichikawa
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Patent number: 8524440Abstract: The present invention provides a photoresist composition comprising a resin which comprises a structural unit represented by the formula (I): wherein Q1 and Q2 independently represent a fluorine atom etc., U represents a C1-C20 divalent hydrocarbon group etc., X1 represents —O—CO— etc., and A+ represents an organic counter ion, and a compound represented by the formula (D?): wherein R51, R52, R53 and R54 independently represent a C1-C20 alkyl group etc., and A11 represents a C1-C36 saturated cyclic hydrocarbon group which may have one or more substituents and which may contain one or more heteroatoms.Type: GrantFiled: January 3, 2011Date of Patent: September 3, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Yuko Yamashita, Nobuo Ando
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Patent number: 8512934Abstract: Compounds of the formula (I), wherein X is a single bond, CRaRb O, S, NRC, NCORC, CO, SO or SO2; L, L1, L2, L3, L4, L5, L6, L7 and L8 are for example hydrogen, R1 or COT; T denotes T1 or O-T2; T1 and T2 for example are hydrogen, C1-C20alkyl, C3-C12cycloalkyl, C2-C20alkenyl, C5-C12cycloalkenyl, C6-C14aryl, C3-C12heteroaryl, C1-C20alkyl substituted by one or more D, C2-C20alkyl interrupted by one or more E, C2-C20alkyl substituted by one or more D and interrupted by one or more E or Q; R1, R2, R3, R4, Ra, Rb and Rc are T1; D is for example R5, OR5, SR5 or Q1; E is for example O, S, COO or Q2; R5 and R6 for example are hydrogen, C1-C12alkyl or phenyl; Q is for example C6-C12bicycloalkyl, C6-C12bicycloalkenyl or C6-C12tricycloalkyl; Q1 is for example, C6-C14aryl or C3-C12heteroaryl; Q2 is for example C6-C14arylene or C3-C12heteroarylene; Y is an anion; and M is a cation; provided that at least one of L, L1, L2, L3, L4, L5, L6, L7 and L8 is other than hydrogen; and provided that (i) at least one of T1 or T2 is a gType: GrantFiled: September 29, 2008Date of Patent: August 20, 2013Assignee: BASF SEInventors: Pascal Hayoz, Hitoshi Yamato
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Patent number: 8507172Abstract: A positive resist composition comprises: (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (B) a resin of which solubility in an alkali developer increases under action of an acid; and (C) a compound capable of decomposing under action of an acid to generate an acid.Type: GrantFiled: January 28, 2008Date of Patent: August 13, 2013Assignee: FUJIFILM CorporationInventor: Kenji Wada
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Patent number: 8507176Abstract: Provided are radiation-sensitive polymers and compositions which may be used in photolithographic processes. The polymers and compositions provide enhanced sensitivity to activating radiation.Type: GrantFiled: December 30, 2010Date of Patent: August 13, 2013Assignee: Rohm and Haas Electronic Materials LLCInventors: James W. Thackeray, Emad Aqad
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Patent number: 8501384Abstract: A positive resist composition comprising a polymer having a tetrahydrobenzocycloheptane-substituted secondary or tertiary carboxyl group ester as an acid labile group exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal edge roughness after exposure, a significant effect of suppressing acid diffusion rate, and improved etching resistance.Type: GrantFiled: January 7, 2011Date of Patent: August 6, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Takeru Watanabe, Seiichiro Tachibana
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Patent number: 8501382Abstract: There are disclosed sulfonic acid precursor compositions, as are methods of using these compositions in, for example, photolithography. Other embodiments are also disclosed.Type: GrantFiled: February 19, 2010Date of Patent: August 6, 2013Assignee: The Research Foundation of State Univ. of New YorkInventor: Robert L. Brainard
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Patent number: 8470513Abstract: A radiation-sensitive resin composition includes a polymer that includes at least one repeating unit (i) selected from a repeating unit shown by a formula (1), (2), and (3); and a repeating unit (ii) shown by a formula (4). R1 represents a hydrogen atom or a methyl group. Each R2 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms. p is an integer from 0 to 3, and q is an integer from 1 to 3, and p+q?5. A chemically-amplified positive-tone resist film that is sensitive to extreme ultraviolet rays (EUV) can be formed using the radiation-sensitive resin composition.Type: GrantFiled: September 23, 2011Date of Patent: June 25, 2013Assignee: JSR CorporationInventors: Kota Nishino, Ken Maruyama, Daisuke Shimizu, Toshiyuki Kai
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Patent number: 8470509Abstract: There is disclosed a negative resist composition wherein a base resin contains at least repeating units represented by the following general formula (1) and general formula (2) and has a weight average molecular weight of 1,000 to 10,000, and the compound containing a nitrogen atom as a basic component contains one or more kinds of amine compounds having a carboxyl group and not having a hydrogen atom covalently bonded to a base-center nitrogen atom. There can be a negative resist composition in which a bridge hardly occurs, substrate dependence is low and a pattern with a high sensitivity and a high resolution can be formed, and a patterning process using the same.Type: GrantFiled: October 12, 2010Date of Patent: June 25, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Akinobu Tanaka, Keiichi Masunaga, Daisuke Domon, Satoshi Watanabe
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Patent number: 8460851Abstract: A salt represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents *—CO—O-La- or *—CH2—O-Lb-, * represents a binding position to —C(Q1)(Q2)-, La and Lb independently represent a C1-C15 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, ring W1 represents a C2-C36 nitrogen-containing heterocyclic group in which one or more —CH2— can be replaced by —O—, and Z1? represents an organic counter ion.Type: GrantFiled: January 6, 2011Date of Patent: June 11, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Koji Ichikawa
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Patent number: 8450041Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes (A) a compound capable of generating a specific acid having a norbornyl structure upon irradiation with an actinic ray or radiation, and (B) a resin capable of increasing the dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure on the resin side chain through a linking group, and a pattern forming method uses the composition.Type: GrantFiled: January 15, 2010Date of Patent: May 28, 2013Assignee: FUJIFILM CorporationInventor: Shuhei Yamaguchi
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Patent number: 8445178Abstract: A composition for radical polymerization includes a photosensitive material, a photoinitiator, a solvent, and a material for adjusting a size of a pattern. A method of forming a pattern using the composition is also disclosed.Type: GrantFiled: June 5, 2009Date of Patent: May 21, 2013Assignee: Samsung Electronics Co., Ltd.Inventors: Jong-jin Park, Kwang-hee Lee, Xavier Bulliard, Yun-hyuk Choi, Kwang-sup Lee
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Patent number: 8440385Abstract: A positive resist composition including a base component (A?) which exhibits increased solubility in an alkali developing solution under the action of acid and generates acid upon exposure, the base component (A?) including a resin component (A1) having a structural unit (a0-1) represented by general formula (a0-1), a structural unit (a0-2) which generates acid upon exposure and a structural unit (a1) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group (wherein R1 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, R2 represents a divalent linking group, and R3 represents a cyclic group containing —SO2— within the ring skeleton thereof).Type: GrantFiled: December 27, 2010Date of Patent: May 14, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Tomoyuki Hirano, Daiju Shiono, Masatoshi Arai
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Patent number: 8440384Abstract: A compound has a partial structure shown by a following formula (1), wherein R1 represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 8 carbon atoms, R2 represents a substituted or unsubstituted hydrocarbon group having 1 to 8 carbon atoms, Rf represents a fluorine atom or a perfluoroalkyl group having 1 to 4 carbon atoms, L represents an integer from 0 to 4, n represents an integer from 0 to 10, and m represents an integer from 1 to 4.Type: GrantFiled: April 14, 2010Date of Patent: May 14, 2013Assignee: JSR CorporationInventors: Takuma Ebata, Tomoki Nagai
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Patent number: 8435717Abstract: A sulfonic acid onium salt represented by the following formula (1) can be used as a superior radiosensitive acid generator for resist compositions. It is possible to form a good pattern by using a resist composition containing this sulfonic acid onium salt. In formula (1), R1 represents a monovalent organic group, and Q+ represents a sulfonium cation or iodonium cation.Type: GrantFiled: February 14, 2008Date of Patent: May 7, 2013Assignee: Central Glass Company, LimitedInventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
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Patent number: 8431323Abstract: 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: GrantFiled: October 29, 2009Date of Patent: April 30, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Satoshi Shinachi, Takeshi Kinsho, Koji Hasegawa, Yuji Harada, Jun Hatakeyama, Kazunori Maeda, Tomohiro Kobayashi
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Patent number: 8431324Abstract: A radiation-sensitive resin composition includes a resin, a radiation-sensitive acid generator, an acid diffusion controller, and a mixed solvent. The radiation-sensitive acid generator includes a compound (I) shown by a following general formula (I). The mixed solvent includes about 50 mass % to about 90 mass % of propylene glycol monomethyl ether acetate, wherein M+ represents a sulfonium cation or an iodonium cation, R represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms, Rf represents a fluorine atom or a perfluoroalkyl group having 1 to 4 carbon atoms, n represents an integer from 1 to 10, and m represents an integer from 1 to 4.Type: GrantFiled: May 7, 2010Date of Patent: April 30, 2013Assignee: JSR CorporationInventors: Tsutomu Shimokawa, Takuma Ebata
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Patent number: 8426113Abstract: The present invention provides chemically amplified silsesquioxane polymers for preparing masks using e-beam lithography. The silsesquioxane polymers have reactive sidechains that in the presence of an acid undergo acid catalyzed rearrangement to generate reactive functionalities that crosslink to form Si—O—Si bonds. The reactive side-chains comprise ?- and ?-substituted alkyl groups bound to the silicon of the silsesquioxane polymer. The substituent of the ?- and ?-substituted alkyl group is an electron withdrawing group. Resists generated with the chemically amplified silsesquioxane polymers of the present invention and imaged with e-beams have resolution of ?60 nm line/space.Type: GrantFiled: August 13, 2010Date of Patent: April 23, 2013Assignee: International Business Machines CorporationInventors: Luisa Dominica Bozano, Blake W. Davis, Alshakim Nelson, Jitendra Singh Rathore, Linda Karin Sundberg
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Patent number: 8426106Abstract: A Photoresist composition comprising a polymer comprising a structural unit derived from a compound represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, R2 represents a C6-C12 aromatic hydrocarbon group which can have one or more substituents, R3 represents a cyano group or a C1-C12 hydrocarbon group which can have one or more substituents and which can contain one or more heteroatoms, A1 represents a single bond, —(CH2)g—CO—O—* or —(CH2)h—O—CO—(CH2)i—CO—O—* wherein g, h and i each independently represent an integer of ?1 to 6 and * represents a binding position to the nitrogen atom, a resin 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, and an acid generator.Type: GrantFiled: October 12, 2010Date of Patent: April 23, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuro Masuyama, Kazuhiko Hashimoto, Junji Shigematsu
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Patent number: 8426101Abstract: A photosensitive composition containing a compound having a specific structure as described in the specification, a pattern-forming method using the photosensitive composition and the compound having a specific structure used in the photosensitive composition.Type: GrantFiled: December 21, 2006Date of Patent: April 23, 2013Assignee: FUJIFILM CorporationInventors: Kenji Wada, Hiromi Kanda
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Patent number: 8420299Abstract: It is therefore an object of the present invention to provide a forming method for a resist pattern to reduce a resist residue in forming the resist pattern on a step whose gradient angle is equal to 90 degrees or more. A forming method for a resist pattern to reduce a resist residue on a step is provided, the method comprising: forming resist film with coating resist containing photo-acid-generator on a step formed on a substrate, where gradient angle of the step is equal to 90 degrees or more, exposing said resist film and generating acid from said photo-acid-generator.Type: GrantFiled: August 6, 2008Date of Patent: April 16, 2013Assignee: TDK CorporationInventors: Hisayoshi Watanabe, Susumu Aoki
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Patent number: 8415085Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) including a compound represented by (b1-1), a compound represented by (b1-1?) and/or a compound represented by (b1-1?) (R1?-R3? represents an aryl group or an alkyl group, provided that at least one of R1?-R3? represents a substituted aryl group being substituted with a group represented by (b1-1-0), and two of R1?-R3? may be mutually bonded to form a ring with the sulfur atom; X represents a C3-C30 hydrocarbon group; Q1 represents a carbonyl group-containing divalent linking group; X10 represents a C1-C30 hydrocarbon group; Q3 represents a single bond or a divalent linking group; Y10 represents —C(?O)— or —SO2—; Y11 represents a C1-C10 alkyl group or a fluorinated alkyl group: Q2 represents a single bond or an alkylene group; and W represents a C2-C10 alkylene group).Type: GrantFiled: May 23, 2012Date of Patent: April 9, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
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Patent number: 8415081Abstract: The present invention discloses a photosensitive resin composition which comprises (A) a compound having a molecule with at least one thiirane ring and a total number of a thiirane ring and/or an epoxy ring of at least 2 in the molecule, and (B) a photo acid generator, said composition having a refractive index of at least 1.6, and a method of obtaining a high refractive index periodical structure which comprises subjecting the photosensitive resin composition to photolithography.Type: GrantFiled: June 17, 2004Date of Patent: April 9, 2013Assignees: Cornell Research Foundation, Inc., Hitachi Chemical Co., Ltd.Inventors: Christopher K. Ober, Yasuharu Murakami
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Patent number: 8404427Abstract: A photosensitive composition containing a compound having a specific structure, a pattern-forming method using the photosensitive composition, and a compound having a specific structure used in the photosensitive composition.Type: GrantFiled: May 24, 2010Date of Patent: March 26, 2013Assignee: FUJIFILM CorporationInventors: Kenji Wada, Kunihiko Kodama
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Patent number: 8394575Abstract: Environmentally friendly thick film layers for a micro-fluid ejection head and micro-fluid ejection heads are disclosed. The environmentally friendly thick film layer includes a negative photoresist layer derived from a composition comprising a multi-functional epoxy compound, a low molecular weight polymeric difunctional epoxy compound, a monomeric difunctional epoxy compound, a methide-based photoacid generator that does not contain antimony, a chromophore and an aryl ketone solvent. Optionally the photoresist layer contains an adhesion enhancer. The negative photoresist layer is environmentally friendly and provides good resolution, well defined critical dimensions, straight side walls, and a large processing window.Type: GrantFiled: September 30, 2010Date of Patent: March 12, 2013Assignee: Lexmark International, Inc.Inventors: Xiaoming Wu, David Graham, Sean Weaver, Bart Mansdorf, Rich Wells, Joel Provence
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Patent number: 8389201Abstract: The present invention relates to a positive resist composition and to a pattern forming process using the same. The present invention provides: a positive resist composition having an enhanced etching resistance and an excellent resolution and being capable of providing an excellent pattern profile even at a substrate-side boundary face of resist, in photolithography for fine processing, and particularly in lithography adopting, as an exposure source, KrF laser, extreme ultraviolet rays, electron beam, X-rays, or the like; and a pattern forming process utilizing the positive resist composition.Type: GrantFiled: May 24, 2010Date of Patent: March 5, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Akinobu Tanaka, Keiichi Masunaga, Daisuke Domon, Satoshi Watanabe
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Patent number: 8377627Abstract: A compound shown by the following formula (1).Type: GrantFiled: July 30, 2008Date of Patent: February 19, 2013Assignee: JSR CorporationInventors: Daisuke Shimizu, Ken Maruyama, Toshiyuki Kai, Tsutomu Shimokawa
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Patent number: 8367299Abstract: 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: GrantFiled: September 15, 2011Date of Patent: February 5, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehiro Seshimo, Tsuyoshi Nakamura, Naoto Motoike, Hiroaki Shimizu, Kensuke Matsuzawa, Hideo Hada
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Patent number: 8367297Abstract: 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) containing a compound having a cation moiety represented by general formula (I) (in the formula, R5 represents a hydrogen atom or an organic group of 1 to 30 carbon atoms which may have a substituent; and Q5 represents a single bond or a divalent linking group).Type: GrantFiled: December 9, 2009Date of Patent: February 5, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Shinichi Hidesaka, Natsuko Maruyama
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Patent number: 8349535Abstract: According to one embodiment, an actinic ray-sensitive or radiation-sensitive resin composition includes (A) a resin containing the repeating units of formulae (I), (II) and (III) that when acted on by an acid, becomes soluble in an alkali developer, and (B) a compound that when irradiated with actinic rays or radiation, generates a fluorine-containing acid, wherein each of R1 independently represents a hydrogen atom or an optionally substituted methyl group, R2 represents a halogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group or an optionally substituted aralkyl group, and n is an integer of 0 to 5, provided that when n is 2 or greater, multiple R2s may be identical to or different from each other.Type: GrantFiled: September 30, 2010Date of Patent: January 8, 2013Assignee: FUJIFILM CorporationInventors: Kana Fujii, Takamitsu Tomiga, Toru Tsuchihashi, Kazuyoshi Mizutani, Jiro Yokoyama, Shinichi Sugiyama, Shuji Hirano, Toru Fujimori
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Patent number: 8338076Abstract: 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) containing a compound having a cation moiety comprising a group represented by general formula (I) (in the formula, R5 represents an organic group having a carbonyl group, an ester bond or a sulfonyl group; and Q represents a divalent linking group).Type: GrantFiled: November 25, 2009Date of Patent: December 25, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Hideo Hada, Takehiro Seshimo, Kensuke Matsuzawa, Keita Ishiduka, Kotaro Endo
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Patent number: 8338077Abstract: This invention relates to new photoacid generator compounds and photoresist compositions that comprise such compounds. In particular, the invention relates to photoacid generator compounds that comprise a multi cyclic lactone moiety.Type: GrantFiled: June 22, 2010Date of Patent: December 25, 2012Assignee: Rohm and Haas Electronic Materials LLCInventors: Mingqi Li, Cheng-Bai Xu, Emad Aqad, Cong Liu
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Patent number: 8338074Abstract: It is intended to provide the following resin composition for stereolithography which is superior in storage stability and aging stability during operation, shows no increase in viscosity upon prolonged storage, has a high light-curing sensitivity and, therefore, makes it possible to produce, upon photo irradiation, an object by stereolithography, which is superior in dimensional accuracy, fabricating accuracy, water resistance, moisture resistance and mechanical properties at a high fabricating speed and a high productivity.Type: GrantFiled: June 24, 2004Date of Patent: December 25, 2012Assignees: CMET Inc., San-Apro Ltd.Inventors: Takashi Ito, Tsuneo Hagiwara, Hideki Kimura, Masashi Date, Jiro Yamamoto
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Patent number: 8334088Abstract: Linear or branched functionalized polycarbosilanes having an absorbance less than 3.0 ?m?1 at 193 nm and a relatively high refractive index are provided. The functionalized polycarbosilanes contain at least one pendant group that is acid labile or aqueous base soluble. Also disclosed are photoresists formulations containing the functionalized polycarbosilanes that are suitable for use in lithography, e.g., immersion lithography.Type: GrantFiled: November 3, 2010Date of Patent: December 18, 2012Assignee: International Business Machines CorporationInventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong