Carbonyl Compound Containing Patents (Class 430/923)
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Patent number: 9682911Abstract: A method for producing an ?-halogenoacetophenon compound includes reacting a specific ?-halogenocarboxylic halide compound and a specific phenyl compound in the presence of a Lewis acid in a solvent, in which the ?-halogenoacetophenon compound and the phenyl compound are reacted with each other in a molar ratio of the Lewis acid to the phenyl compound represented below.Type: GrantFiled: March 21, 2016Date of Patent: June 20, 2017Assignee: FUJIFILM CorporationInventors: Katsuyuki Yofu, Akihito Amao, Katsuhiro Shimono
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Patent number: 9012129Abstract: 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: January 6, 2014Date of Patent: April 21, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
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Patent number: 9005871Abstract: Compounds of the formula (I), wherein Ar1 is for example phenylene or biphenylene both unsubstituted or substituted; Ar2 and Ar3 are for example independently of each other phenyl, naphthyl, biphenylylyl or heteroaryl, all optionally substituted; or Ar1 and Ar2 for example together with a direct bond, O, S or (CO), form a fused ring system; R is for example hydrogen, C3-C30cycloalkyl or C1-C18alkyl; and R1, R2 and R3 independently of each other are for example C1-C10haloalkyl; are effective photoacid generators (PAG).Type: GrantFiled: October 8, 2009Date of Patent: April 14, 2015Assignee: BASF SEInventors: Hitoshi Yamato, Toshikage Asakura, Yuichi Nishimae
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Patent number: 8956805Abstract: Polymers, methods of use thereof, and methods of decomposition thereof, are provided. One exemplary polymer, among others, includes, a photodefinable polymer having a sacrificial polymer and a photoinitiator.Type: GrantFiled: May 7, 2013Date of Patent: February 17, 2015Assignee: Georgia Tech Research CorporationInventors: Paul A. Kohl, Sue Ann Bidstrup-Allen, Clifford Lee Henderson
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Patent number: 8940473Abstract: A resist composition contains (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 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; R3 and R4 independently represent a fluorine atom or a C1 to C6 perfluoroalkyl group; X1 represents an C1 to C17 divalent saturated hydrocarbon group; R5 represents a group having cyclic ether structure; and Z1+ represents an organic cation.Type: GrantFiled: February 24, 2012Date of Patent: January 27, 2015Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Yuichi Mukai, Satoshi Yamamoto
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Patent number: 8889336Abstract: 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: GrantFiled: May 30, 2013Date of Patent: November 18, 2014Assignee: JSR CorporationInventor: Ken Maruyama
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Patent number: 8808959Abstract: 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: November 10, 2009Date of Patent: August 19, 2014Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
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Patent number: 8791293Abstract: According to the present invention, there is provided a fluorine-containing sulfonate resin having a repeating unit of the following general formula (3). In order to prevent deficiency such as roughness after pattern formation or failure in pattern formation, the fluorine-containing sulfonate resin incorporates therein a photoacid generating function and serves as a resist resin in which “a moiety capable of changing its developer solubility by the action of an acid” and “a moiety having a photoacid generating function” are arranged with regularity.Type: GrantFiled: August 2, 2012Date of Patent: July 29, 2014Assignee: Central Glass Company, LimitedInventors: Kazunori Mori, Satoru Narizuka, Fumihiro Amemiya, Masaki Fujiwara
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Patent number: 8697332Abstract: An object of the present invention is to provide a base generator which has sensitivity and is applicable to a wide range of applications, and a photosensitive resin composition which is applicable to a wide range of applications due to the structure of a polymer precursor in which reaction into a final product is promoted by a basic substance or by heating in the presence of a basic substance. The base generator generates a base by exposure to electromagnetic radiation and heating. The photosensitive resin composition comprises a polymer precursor in which reaction into a final product is promoted by the base generator and a basic substance or by heating in the presence of a basic substance.Type: GrantFiled: March 26, 2010Date of Patent: April 15, 2014Assignee: Dai Nippon Printing Co., Ltd.Inventors: Mami Katayama, Shunji Fukuda, Katsuya Sakayori, Kouji Kawaguchi
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Patent number: 8617786Abstract: The present invention relates to compositions comprising poly-oxycarbosilane and methods for using the compositions in step and flash imprint lithography. The imprinting compositions comprise a poly-oxycarbosilane polymer, a silanol, a reaction initiator and optionally a pore generator.Type: GrantFiled: February 11, 2011Date of Patent: December 31, 2013Assignee: International Business Machines CorporationInventors: Richard Anthony Dipietro, Geraud Jean-Michel Dubois, Robert Dennis Miller, Ratnam Sooriyakumaran
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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: 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: 8557498Abstract: A photosensitive resin composition is used that comprises a photosensitive silicone having a styryl group as a photosensitive group, and a photopolymerization initiator having a specific structure. As a result, a photosensitive resin composition capable of being cured in air by photopolymerization that is preferable for use as a buffer coat material or rewiring layer of an LSI chip, a method for forming a cured relief pattern using this photosensitive resin composition, and a semiconductor device comprising the cured relief pattern are provided.Type: GrantFiled: March 25, 2008Date of Patent: October 15, 2013Assignee: Asahi Kasei E-Materials CorporationInventor: Tomohiro Yorisue
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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: 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: 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: 8349533Abstract: A resist lower-layer composition configured to be used by a multi-layer resist method used in lithography to form a layer lower than a photoresist layer acting as a resist upper layer film. The resist lower-layer composition is insoluble or poorly-soluble in an alkaline developer after formation of the lower layer, and the resist lower-layer composition comprises, at least, a thermal acid generator for generating an acid by heating at a temperature of 100° C. or higher.Type: GrantFiled: October 20, 2009Date of Patent: January 8, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Jun Hatakeyama, Takeru Watanabe, Takeshi Kinsho
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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: 8211619Abstract: The present invention provides: a positive photosensitive composition that yields an insulation layer superior not only in high transparency, but also in heat resistance enduring a temperature during the production of a substrate, solvent resistance, and anti-aging property as a permanent resist; a positive permanent resist utilizing the positive photosensitive composition; and a method for producing the positive permanent resist. The present invention provides: a positive photosensitive composition containing (A) a curable silicone resin having a silanol group, which resin has a structure obtained by a reaction between one or more cyclic siloxane compounds represented by the following general formula (1): and one or more arylalkoxysilane compounds represented by the following general formula (2): (B) diazonaphthoquinones, and (C) a solvent; a positive permanent resist using the positive photosensitive composition; and a method for producing the positive permanent resist.Type: GrantFiled: November 12, 2008Date of Patent: July 3, 2012Assignee: Adeka CorporationInventors: Hiroshi Morita, Hiromi Sato, Atsushi Kobayashi, Jinichi Omi, Seiichi Saito
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Patent number: 8148044Abstract: A positive photosensitive composition includes at least one compound that when exposed to actinic rays or radiation, generates any of the sulfonic acids of general formula (I) and a resin whose solubility in an alkali developer is increased by the action of an acid, wherein each of X1 and X2 independently represents a fluorine atom or a fluoroalkyl group, R1 represents a group with a polycyclic structure, provided that the polycyclic structure may have a substituent, and R2 represents a hydrogen atom, a chain alkyl group, a monocyclic alkyl group, a group with a polycyclic structure or a monocyclic aryl group, provided that each of the chain alkyl group, monocyclic alkyl group, polycyclic structure and monocyclic aryl group may have a substituent, and provided that R1 and R2 may be bonded to each other to thereby form a polycyclic structure.Type: GrantFiled: October 29, 2009Date of Patent: April 3, 2012Assignee: Fujifilm CorporationInventors: Shuhei Yamaguchi, Tomotaka Tsuchimura, Yuko Tada
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Patent number: 8057985Abstract: A polymerizable anion-containing sulfonium salt having formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2, R3 and R4 are C1-C10 alkyl, alkenyl or oxoalkyl or C6-C18 aryl, aralkyl or aryloxoalkyl, or two of R2, R3 and R4 may bond together to form a ring with S, A is a C1-C20 organic group, and n is 0 or 1. The sulfonium salt generates a very strong sulfonic acid upon exposure to high-energy radiation. A resist composition comprising a polymer derived from the sulfonium salt is also provided.Type: GrantFiled: August 27, 2009Date of Patent: November 15, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa, Jun Hatakeyama, Seiichiro Tachibana
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Patent number: 8048613Abstract: An alkali development-type solder resist includes (A) a carboxyl group-containing photosensitive resin obtained by reacting (a) a compound having two or more cyclic ether or thioether groups in the molecule with (b) an unsaturated monocarboxylic acid, reacting the product with (c) a polybasic acid anhydride, reacting the resulting resin with (d) a compound having a cyclic ether group and an ethylenic unsaturated group in the molecule, and reacting the product additionally with (c) a polybasic acid anhydride, (B) an oxime ester-based photopolymerization initiator containing a specific oxime ester group, (C) a compound having two or more ethylenic unsaturated groups in the molecule, and (D) a thermosetting component, wherein the dry film obtained by applying the composition has an absorbance of 0.3 to 1.2 per 25 ?m of the film thickness at a wavelength of 350 to 375 nm.Type: GrantFiled: October 13, 2008Date of Patent: November 1, 2011Assignee: Taiyo Ink Mfg. Co., Ltd.Inventors: Nobuhito Itoh, Yoko Shibasaki, Kenji Kato, Masao Arima
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Patent number: 8021823Abstract: There is provided a positive resist composition, including a base component (A) which exhibits increased solubility in an alkali developing solution under action of an acid, and an acid generator component (B) which generates an acid upon exposure, wherein the base component (A) includes a polymeric compound (A1) containing a structural unit (a0) represented by the general formula (a0-1) shown below: (wherein, R1 represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; A represents a bivalent linking group; B represents a bivalent linking group; and R2 represents an acid dissociable, dissolution inhibiting group).Type: GrantFiled: February 18, 2009Date of Patent: September 20, 2011Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Takahiro Dazai, Daiju Shiono, Tomoyuki Hirano
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Patent number: 7927780Abstract: 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: GrantFiled: September 10, 2008Date of Patent: April 19, 2011Assignee: 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
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Patent number: 7927781Abstract: The present invention relates to a photosensitive resin composition including a) an alkali-soluble acrylate resin, b) a cross-linking monomer having at least two ethylenic double bonds, and c) a phosphinoxide based photopolymerization initiator and an acridon based photopolymerization initiator; a preparation method thereof; and a dry film resist comprising the same.Type: GrantFiled: December 4, 2008Date of Patent: April 19, 2011Assignee: Dongjin Semichem Co., Ltd.Inventors: In-Ho Yoon, Bong-Gi Kim, Chang-Seok Rho, Sang-Ki Kang, Kyung-Rock Byun, Chan-Seok Park
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Patent number: 7695891Abstract: A photosensitive composition comprising a compound capable of generating a compound having a specific structure upon irradiation with actinic rays or radiation; a pattern forming method using the photosensitive composition; a compound having a specific structure; and a compound capable of generating a compound having a specific structure upon irradiation with actinic rays or radiation.Type: GrantFiled: June 21, 2006Date of Patent: April 13, 2010Assignee: FUJIFILM CorporationInventor: Kenji Wada
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Patent number: 7569326Abstract: 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: GrantFiled: October 25, 2007Date of Patent: August 4, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama, Takeru Watanabe
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Patent number: 7560219Abstract: 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: GrantFiled: April 26, 2007Date of Patent: July 14, 2009Assignee: Henkel AG & Co. KGaAInventors: Yuxia Liu, Donald E. Herr
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Patent number: 7510822Abstract: 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: GrantFiled: April 9, 2003Date of Patent: March 31, 2009Assignee: FUJIFILM CorporationInventor: Kunihiko Kodama
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Patent number: 7378223Abstract: The invention provides photoresist resin compositions and in particular, a photoresist resin compositions comprising a) an acrylate monomer having two urethane bonds, b) a crosslinkable urethane monomer having at least two ethylene double bonds, c) an alkali-soluble compound, d) a photopolymerization initiator and e) a solvent, and a photoresist dry film resists using the photoresist resins. The photoresist resin compositions and the photoresist dry film resists using the same in accordance with the invention have excellent adhesion to a substrate and sandblast resistance and at the same time, they have high sensitivity as well as high resolution, thereby enabling fine pattern formation on substrates.Type: GrantFiled: May 6, 2005Date of Patent: May 27, 2008Assignee: Dongjin Semichem, Co., Ltd.Inventors: Bong-gi Kim, Sung-mun Ryu, Seong-mo Park, Chan-seok Park
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Patent number: 7374868Abstract: Disclosed are a composition for an organic bottom anti-reflective coating able to improve the uniformity of a photoresist pattern with respect to an ultra-fine pattern formation process among processes for manufacturing semiconductor device, which prevents scattered reflection from the bottom film layer and eliminating the standing wave effect due to alteration of the thickness of the photoresist film itself resulting in increase of uniformity of the photoresist pattern. The composition for organic bottom anti-reflective coating is able to reduce amount of polyvinylphenol by introducing a specific light absorbent agent having an etching velocity higher than of the polyvinylphenol, thus notably improving the etching velocity for the organic anti-reflective coating by about 1.5 times, so that and the present composition prevents over-etching of the photoresist to make it possible to conduct a smooth etching process for a layer to be etched.Type: GrantFiled: August 3, 2004Date of Patent: May 20, 2008Assignee: Hynix Semiconductor Inc.Inventor: Jae-chang Jung
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Patent number: 7368224Abstract: 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: GrantFiled: April 3, 2003Date of Patent: May 6, 2008Assignee: Kyowa Hakko Chemical Co., Ltd.Inventors: Tsuguo Yamaoka, Ikuo Shimizu, Hiroshi Toyoda, Motoharu Kinugasa, Masanori Ikuta, Kyoko Katagi
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Patent number: 7364834Abstract: A polymer having ?,? unsaturated groups and a group that generates a free radical when exposed to actinic radiation. The polymer may be self-cross-linking.Type: GrantFiled: July 13, 2005Date of Patent: April 29, 2008Assignee: Rohm and Haas Electronic Materials LLCInventors: Robert K. Barr, Edgardo Anzures, Daniel E. Lundy
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Patent number: 7312013Abstract: This invention provides a photoreactive composition in which reaction of a hydrolyzable metal compound takes place by irradiation of light. A photoreactive composition, which comprises a hydrolyzable metal compound (A) comprising a metal atom and a hydrolyzable functional group bonded to the metal atom and, a compound (B) promoting reaction, polymerization or crosslinking of the compound (A) in the presence of oxygen by irradiation of light.Type: GrantFiled: April 9, 2002Date of Patent: December 25, 2007Assignee: Sekisui Chemical Co., Ltd.Inventors: Katsunori Takahashi, Hiroji Fukui, Kazuhiro Kawabata, Takeo Kuroda, Motokuni Ichitani, Yasuhiro Nakatani
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Patent number: 7300747Abstract: The photobase generator of the invention is represented by the following formula 1: wherein Ar, R, A+ and X? are as defined in the specification. Since the photobase generator of the formula 1 absorbs ultraviolet lights of relatively long wavelength and is photolyzed to generate a strong base efficiently, a composition containing the photobase generator and an episulfide compound is easily cured by polymerization under ultraviolet irradiation.Type: GrantFiled: February 7, 2005Date of Patent: November 27, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hitoshi Okazaki, Junya Hayakawa, Motoharu Takeuchi, Masahiro Jono, Kenji Ishii
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Patent number: 7214471Abstract: The photosensitive resin film in an uncured state of the invention comprises (A) a specific alkali-soluble copolymer, (B) a compound having at least one ethylenically unsaturated double bond and (C) a radiation-sensitive radical polymerization initiator by the use of which a coating film having a dry film thickness of 70 ?m in an uncured state has a 365 nm radiation transmittance of not less than 10% and a 405 nm radiation transmittance of not less than 60%, contains the radiation-sensitive radical polymerization initiator (C) in an amount of 20 to 40 parts by weight based on 100 parts by weight of the component (A), and has a dry film thickness of not less than 50 ?m. According to the photosensitive resin film, a high bump having a height of not less than 50 ?m can be readily formed on a chip substrate with high precision though formation of such a high bump is difficult by the conventional technique. Moreover, connection failure of an element can be inhibited, and reliability of an element can be enhanced.Type: GrantFiled: March 25, 2004Date of Patent: May 8, 2007Assignee: JSR CorporationInventors: Shin-ichiro Iwanaga, Tooru Kimura, Kouji Nishikawa
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Patent number: 7033727Abstract: A photosensitive composition of the present invention has excellent sensitivity and pattern profile, which comprises an acid generator having a specific structure.Type: GrantFiled: September 24, 2003Date of Patent: April 25, 2006Assignee: Fuji Photo Film Co., Ltd.Inventor: Kunihiko Kodama
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Patent number: 7001706Abstract: A sulfonate of the formula (I): wherein Q1, Q2, Q3, Q4 and Q5 each independently represents a certain substituent, and A+ represents a counter ion, with the proviso that at least one of Q1, Q2, Q3, Q4 and Q5 is a group of the formula (II) wherein R1 and R2 each independently an alkyl having 1 to 12 carbon atoms or the like; and a chemical amplification type positive resist composition comprising the sulfate 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: GrantFiled: July 16, 2004Date of Patent: February 21, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Makoto Akita, Isao Yoshida
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Patent number: 6838222Abstract: A photopolymerizable composition that is cured with visible light or an infrared laser and is used as a recording layer in a negative planographic printing plate precursor. The photopolymerizable composition is cured by exposure and includes (A) a polymerizable compound that is solid at 25° C. and has at least one radical-polymerizable ethylenically unsaturated double bond in a molecule, (B) a radical polymerization initiator, (C) a binder polymer and, as required, (D) a compound generating heat by infrared exposure.Type: GrantFiled: February 14, 2002Date of Patent: January 4, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Keitaro Aoshima, Kazuhiro Fujimaki
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Publication number: 20040241569Abstract: A chemically-amplified resist composition is disclosed, which comprises a polymer of formula (I) below: 1Type: ApplicationFiled: May 28, 2003Publication date: December 2, 2004Applicant: Everlight USA, Inc.Inventors: Chi-Sheng Chen, Chan-Chan Tsai, Bin Jian, Hsin-Ming Liao
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Publication number: 20040241591Abstract: The invention relates to a reaction development patterning process wherein a photo resist layer masked by a desired pattern is irradiated using ultraviolet light and this layer is subsequently washed using a solvent solution containing alkali characterized by said photo resist layer comprising a condensation type polymer containing in the main chain carbonyl groups (C═O) bonded to hetero atoms and a photo acid generating agent and said alkali being an amine. This reaction development patterning process is characterized by being able to use as a photo resist target resins containing bonds having low reactivity toward nucleophilic reagents, for example, condensation type polymers containing any one of bonds such as carbonate, ester, urethane and amide.Type: ApplicationFiled: April 2, 2004Publication date: December 2, 2004Inventors: Masao Tomoi, Takafumi Fukushima, Hiroshi Itatani
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Patent number: 6818375Abstract: Disclosed are photoimageable compositions having improved stripping properties including a photoresist strip enhancer. Also disclosed are methods of enhancing the strippability of photoimageable compositions and methods for manufacturing printed wiring boards using such photoimageable compositions.Type: GrantFiled: November 28, 2001Date of Patent: November 16, 2004Assignee: Eternal Technology CorporationInventors: Thomas A. Koes, Todd Johnson
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Publication number: 20040219457Abstract: A photopolymerisable system is disclosed which can be polymerised by exposure to UV light, for example, to form a solid, light-transmitting sheet material having volume refractive index variations defining an optical diffuser or a hologram, for example. The system includes a silicone monomer, prepolymer, macromonomer or co-monomer capable of undergoing free radical initiated polymerization and further includes a photoinitiator.Type: ApplicationFiled: October 16, 2003Publication date: November 4, 2004Inventors: Robin J.T. Clabburn, Rifat Iqbal, Stephen Moratti
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Patent number: 6808862Abstract: A positive photosensitive composition comprising (A1) a compound that generates an alkanesulfonic acid in which the &agr;-position is substituted with a fluorine atom upon irradiation of an actinic ray or radiation, (A2) an onium salt of an alkanesulfonic acid in which the &agr;-position is not substituted with a fluorine atom, and (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase a solubility rate in an alkali developing solution.Type: GrantFiled: June 20, 2002Date of Patent: October 26, 2004Assignee: Fuji Photo Film Co., Ltd.Inventor: Kunihiko Kodama
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Patent number: 6767686Abstract: A chemically amplifying type positive resist composition suitable for use in the lithography utilizing an ArF or KrF excimer laser and excellent in the shape of profile is provided, which comprises a resin which has an alkali-soluble group protected by 2-alkyl-2-adamantyl group or 1-adamantyl-1-alkylalkyl group, and which, per se, is insoluble or slightly soluble in alkali but becomes soluble in alkali by the action of an acid; and a sulfonium salt acid generating agent represented by the following formula (I): wherein Q1, Q2 and Q3 independently represent hydrogen, hydroxyl, alkyl having 1 to 6 carbon atoms or alkoxy having 1 to 6 carbon atoms; and Q4 represents perfluoroalkyl which may have a cyclic structure.Type: GrantFiled: November 16, 2001Date of Patent: July 27, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Yasunori Uetani, Kenji Ohashi, Hiroshi Moriuma
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Publication number: 20040091816Abstract: A photosensitive composition exhibiting enhanced sensitivity is disclosed, comprising an ethylenically unsaturated monomer, a photopolymerization initiator composition and a polymer binder, wherein the photopolymerization initiator composition contains a polyhalogen compound. There is also disclosed a photosensitive lithographic printing plate comprising the foregoing photosensitive composition on a support having a hydrophilic surface.Type: ApplicationFiled: October 17, 2003Publication date: May 13, 2004Applicant: Konica Minolta Holdings, Inc.Inventors: Toshiyuki Matsumura, Kazuhiko Hirabayash
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Patent number: 6727038Abstract: A photodefineable mixture comprising oligomeric divinyltetramethyldisiloxane bisbenzocyclobutene as its major resin component dissolved in mesitylene and at least 2,6-bis(4-azidobenzylidene)-4-ethylcyclohexanone as a photosensitive agent in an amount sufficient to convert the mixture to an organic-insoluble solid upon exposing the mixture to photon radiation is disclosed. These polymer compositions are useful as thin film dielectrics in electronic applications such as multichip modules, integrated circuits and printed circuit boards.Type: GrantFiled: July 20, 2001Date of Patent: April 27, 2004Assignee: Dow Global Technologies Inc.Inventors: Ying Hung So, Cheryl L. Murlick, Daniel M. Scheck, Gregory S. Becker, Eric S. Moyer
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Publication number: 20040067431Abstract: A photoreactive composition comprises (a) at least one reactive species that is capable of undergoing an acid- or radical-initiated chemical reaction; and (b) a photoinitiator system comprising photochemically-effective amounts of (1) at least one type of semiconductor nanoparticle quantum dot that has at least one electronic excited state that is accessible by absorption of two or more photons, and (2) a composition, different from said reactive species, that is capable of interacting with the excited state of the semiconductor nanoparticle quantum dot to form at least one reaction-initiating species.Type: ApplicationFiled: October 2, 2002Publication date: April 8, 2004Applicant: 3M Innovative Properties CompanyInventors: David S. Arney, Catherine A. Leatherdale, Manoj Nirmal
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Publication number: 20040067433Abstract: A method of multiphoton photosensitizing comprisesType: ApplicationFiled: October 2, 2002Publication date: April 8, 2004Applicant: 3M Innovative Properties CompanyInventors: Manoj Nirmal, Catherine A. Leatherdale, David S. Arney
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Patent number: 6703190Abstract: A method for creating negative resist structures is described. In the method, a chemically fortified resist is applied to a substrate, dried, irradiated with light, x-ray, electron or ion beams, heated, developed using a aqueous-alkaline developer solution and siliconized from a liquid phase. The resist contains the following constituent: a polymer, whose polarity is modified by acidic action and which contains carboxylic acid anhydride groups, preferably in latent form; a compound which releases an acid as a result of thermal treatment; a photoreactive compound, from which a base is created during the irradiation with light, x-ray, electron or ion beams; a solvent; and optionally one or more additives.Type: GrantFiled: June 7, 2002Date of Patent: March 9, 2004Assignee: Infineon Technologies AGInventors: Klaus Elian, Stefan Hien, Ernst-Christian Richter, Michael Sebald