Cationic Or Anionic Patents (Class 430/914)
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Patent number: 8110336Abstract: A resin comprising a structural unit represented by the formula (I): wherein Q1 and Q2 represent a fluorine atom etc., U represents a C1-C20 divalent hydrocarbon group in which one or more —CH2— may be replaced by —O— etc., X1 represents —O—CO— etc., and A+ represents an organic counter ion.Type: GrantFiled: September 18, 2009Date of Patent: February 7, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Ichiki Takemoto, Nobuo Ando
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Patent number: 8092978Abstract: Provided is a positive resist composition for an electron beam, an X-ray or EUV, including: (A) a resin capable of decomposing by the action of an acid to increase the dissolution rate in an aqueous alkali solution; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, represented by the following formula (ZI) or (ZII); (C) a basic compound; and (D) an organic solvent, wherein a concentration of all solid contents in said composition is from 1.0 to 4.5 mass %, and a total amount of the compound represented by formula (ZI) or (ZII) is 12 mass % or more based on all solid contents in said composition: wherein symbols in the formulae are defined in the specification.Type: GrantFiled: March 25, 2009Date of Patent: January 10, 2012Assignee: Fujifilm CorporationInventor: Katsuhiro Yamashita
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Patent number: 8071270Abstract: The present invention provides a polyhydric compound represented by the formula (I): wherein R51 to R67 each independently represent a hydrogen atom etc., at least one selected from the group consisting of R1 to R5 is a group represented by the formula (II): wherein Q1 and Q2 each independently represent a fluorine atom etc., U represents a C1-C20 divalent hydrocarbon group etc., and A+ represents an organic counter ion, and the others are hydrogen atoms or groups represented by the formula (III): wherein X1 to X4 each independently represent a hydrogen atom etc., n represents an integer of 0 to 3, W represents any one of the following groups: Z1 represents a C1-C6 alkyl group etc., and ring Y represents a C3-C20 alicyclic hydrocarbon group, and a chemically amplified resist composition containing the same.Type: GrantFiled: February 23, 2009Date of Patent: December 6, 2011Assignee: Sumitomo Chemical Company, LimitedInventors: Ichiki Takemoto, Nobuo Ando
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Patent number: 8053172Abstract: Photolithography compositions and methods. A first layer of a first photoresist is formed on a substrate. A second layer of a second photoresist is formed directly onto the first layer. The second polymer of the second photoresist includes an absorbing moiety. The second layer is patternwise imaged and developed, resulting in removal of base-soluble regions. A relief pattern from the second layer remains. The relief pattern and the first layer are exposed to a second dose of the radiation. The polymer in the relief pattern absorbs a portion of the second dose. A fraction of the second dose passes through the at least one region of the relief pattern and exposes at least one region of the first layer. The relief pattern and base-soluble regions of the first layer are removed. A relief pattern from the first layer remains. A second photolithography method and a photoresist composition are also included.Type: GrantFiled: February 21, 2008Date of Patent: November 8, 2011Assignee: International Business Machines CorporationInventors: Scott David Halle, Wu-Song Huang, Ranee Wai-Ling Kwong, Pushkara R. Varanasi
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Patent number: 8043789Abstract: A photosensitive compound whose size is smaller than conventional polymer for photoresist, and which has well-defined (uniform) structure, and a photoresist composition including the same are disclosed. The photosensitive compound represented by the following formula. Also, the present invention provides a photoresist composition comprising 1 to 85 wt % (weight %) of the photosensitive compound; 0.05 to 15 weight parts of a photo-acid generator with respect to 100 weight parts of the photosensitive compound; and 10 to 5000 weight parts of an organic solvent. In the formula, n is 0 or 1, x is 1, 2, 3, 4 or 5, y is 2, 3, 4, 5 or 6, z is 0, 1, 2, 3 or 4, R, R? and R? are independently hydrocarbon group of 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms, and R?? is a hydrogen atom or hydrocarbon group of 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms.Type: GrantFiled: December 17, 2008Date of Patent: October 25, 2011Assignee: Dongjin Semichem Co., Ltd.Inventors: Jae-Woo Lee, Min-Ja Yoo, Jun-Gyeong Lee, Young-Bae Lim, Jae-Hyun Kim
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Patent number: 8043786Abstract: The invention provides novel acid generators which are unproblematic in combustibility and accumulation inside the human body and can generate acids having high acidities and high boiling points and exhibiting properly short diffusion lengths in resist coating films and which permit the formation of resist patterns excellent smoothness with little dependence on the denseness of a mask pattern; sulfonic acids generated from the acid generators; sulfonyl halides useful as raw material in the synthesis of the acid generators; and radiation-sensitive resin compositions containing the acid generators. The acid generators have structures represented by the general formula (I), wherein R1 is a monovalent substituent such as alkoxycarbonyl, alkylsulfonyl, or alkoxysulfonyl; R2 to R4 are each hydrogen or alkyl; k is an integer of 0 or above; and n is an integer of 0 to 5.Type: GrantFiled: February 20, 2004Date of Patent: October 25, 2011Assignee: JSR CorporationInventors: Satoshi Ebata, Yong Wang, Isao Nishimura
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Patent number: 8034546Abstract: The use as a resist material of a methanofullerene derivative having a plurality of open-ended addends, and to a method for forming a patterned resist layer on a substrate using the methanofullerene derivatives. The methanofullerene derivatives can be represented by the formal C2x(CR1R2)m where x is at least 10, m is at least 2, each addend represented by CR1R2 is the same or different, and wherein each R1 and R2 is each a monovalent organic group, or a divalent organic group which forms a ring structure by being joined to the fullerene shell, or where both R1 and R2 of an addend are divalent groups, they may be mutually joined to form a ring structure, save that at least two of R1 or two of R2 are monovalent, or a mixture of such derivatives. The use of any methanofullerene derivative which has been chemically amplified for formation of a patterned resist layer.Type: GrantFiled: September 19, 2005Date of Patent: October 11, 2011Assignee: The University of BirminghamInventors: Alex Robinson, Jon Andrew Preece, Richard Edward Palmer
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Patent number: 8029971Abstract: Compositions, a method, and a photopatternable blend. The compositions include a blend of a first and a second polymer. The first polymer is a substituted silsesquioxane copolymer. The second polymer is a substituted silsesquioxane polymer. The second polymer is configured to undergo chemical crosslinking with the first polymer, the second polymer, or a combination thereof, upon exposure to light, thermal energy, or a combination thereof. The compositions include a photosensitive acid generator. The method includes forming a film. The film is patternwise imaged, and at least one region is exposed to radiation. After the imaging, the film is baked, wherein at least one exposed region is rendered substantially soluble. After the baking, the film is developed, wherein a relief pattern remains. The relief pattern is exposed to radiation. The relief pattern is baked. The relief pattern is cured. A chemically amplified positive-tone photopatternable blend is also described.Type: GrantFiled: March 13, 2008Date of Patent: October 4, 2011Assignee: International Business Machines CorporationInventors: Robert D. Allen, Phillip Joe Brock, Blake W. Davis, Qinghuang Lin, Robert D. Miller, Alshakim Nelson, Ratnam Sooriyakumaran
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Patent number: 8012671Abstract: A curable composition in which polymerization inhibition due to oxygen is suppressed and which may be cured with high sensitivity by exposure to laser light or the like is provided. The curable composition includes: a polymerizable compound having an ethylenically unsaturated bond; a binder; a radical polymerization initiator; and at least one specific amine compound. Also provided is an image forming material and a negative-working planographic printing plate precursor including the curable composition.Type: GrantFiled: September 24, 2008Date of Patent: September 6, 2011Assignee: FUJIFILM CorporationInventor: Shigefumi Kanchiku
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Patent number: 8003293Abstract: A deliberately engineered placement and size constraint (molecular weight distribution) of photoacid generators, solubility switches, photoimageable species, and quenchers forms individual pixels within a photoresist. Upon irradiation, a self-contained reaction occurs within each of the individual pixels that were irradiated to pattern the photoresist. These pixels may take on a variety of forms including a polymer chain, a bulky cluster, a micelle, or a micelle formed of several polymer chains. Furthermore, these pixels may be designed to self-assemble onto the substrate on which the photoresist is applied.Type: GrantFiled: September 30, 2004Date of Patent: August 23, 2011Assignee: Intel CorporationInventors: Robert P. Meagley, Michael D. Goodner, Bob E. Leet, Michael L. McSwiney
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Patent number: 7977028Abstract: The present invention provides a photosensitive resin composition comprising (a) an alkali-soluble resin, (b) a silicon compound having a secondary aromatic amino group and an alkoxy group, and (c) at least one selected from a photopolymerization initiator, a photo acid generator and a photo base generator. According to the present invention, it is possible to obtain a photosensitive resin composition which remarkably enhances the adhesion property with a substrate after curing without deteriorating storage stability of a solution, and does not cause peeling of a fine pattern even upon development.Type: GrantFiled: April 18, 2006Date of Patent: July 12, 2011Assignee: Toray Industries, Inc.Inventors: Tomoyuki Yuba, Yoji Fujita, Masao Tomikawa
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Patent number: 7947423Abstract: A photosensitive compound whose size is smaller than conventional polymer for photoresist, and which has well-defined (uniform) structure, and a photoresist composition including the same are disclosed. The photosensitive compound represented by the following formula 1. Also, the photoresist composition comprises 1 to 85 wt % (weight %) of the photosensitive compound; 0.05 to 15 weight parts of a photo-acid generator with respect to 100 weight parts of the photosensitive compound; and 200 to 5000 weight parts of an organic solvent. In the formula 1, x is 1, 2, 3, 4 or 5, y is 2, 3, 4, 5 or 6, and R and R? are independently a chain type or a ring type of aliphatic or aromatic hydrocarbon group of 1 to 30 carbon atoms.Type: GrantFiled: September 11, 2008Date of Patent: May 24, 2011Assignee: Dongjin Semichem Co., Ltd.Inventors: Jae-Woo Lee, Min-Ja Yoo, Jun-Gyeong Lee, Young-Bae Lim, Jae-Hyun Kim
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Patent number: 7939241Abstract: The present invention relates to a novel (meth)acrylamide compound represented by the general formula (1), a (co)polymer of the (meth)acrylamide compound, and a chemically amplified photosensitive resin composition composed of the polymer and a photoacid generator. In the formula, R1 represents a hydrogen atom or a methyl group; R2 represents an acid-decomposable group; and R3 to R6 independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms.Type: GrantFiled: May 12, 2006Date of Patent: May 10, 2011Assignee: NEC CorporationInventors: Katsumi Maeda, Kaichirou Nakano
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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: 7923195Abstract: The present invention provides a polymer suitable as a base resin for a positive resist composition, especially for a chemically amplified positive resist composition, having a high sensitivity, a high degree of resolution, a good pattern configuration after exposure, and in addition an excellent etching resistance; a positive resist composition using the polymer; and a patterning process. The positive resist composition of the present invention is characterized in that it contains at least, as a base resin, a polymer whose hydrogen atom of a phenolic hydroxide group is substituted by an acid labile group represented by the following general formula (1).Type: GrantFiled: January 22, 2009Date of Patent: April 12, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Takanobu Takeda
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Patent number: 7906269Abstract: Disclosed is a fluorine-containing polymer compound containing first and second repeating units respectively represented by formulas (a-1) and (a-2), wherein R3 represents a fluorine atom or fluorine-containing alkyl group, each of W and W1 independently represents a bivalent linking group, R2 represents an acid-labile protecting group, each of R4, R5 and R6 independently represents a hydrogen atom, fluorine atom or monovalent organic group, and at least two of R4, R5, R6 and W or W1 may be combined to form a cyclic structure in formula (a-1) or (a-2). This polymer compound has a weight-average molecular weight of 1,000 to 1,000,000 and can provide a resist composition capable of forming a pattern with no swelling and no pattern falling down.Type: GrantFiled: August 28, 2008Date of Patent: March 15, 2011Assignee: Central Glass Company, LimitedInventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiro Yamanaka
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Patent number: 7901871Abstract: 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: GrantFiled: January 9, 2008Date of Patent: March 8, 2011Assignee: Samsung Electronics Co., Ltd.Inventors: Sung-ouk Jung, Seung-ju Seo, Jae-chan Park
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Patent number: 7892720Abstract: To provide a negative photosensitive fluorinated aromatic resin composition having a low relative permittivity, low water absorptivity, high heat resistance and high productivity. A negative photosensitive fluorinated aromatic resin composition comprising the following fluorinated aromatic prepolymer, a photosensitizer and a solvent.Type: GrantFiled: September 15, 2008Date of Patent: February 22, 2011Assignee: Asahi Glass Company, LimitedInventors: Takeshi Eriguchi, Hiromasa Yamamoto, Kaori Tsuruoka
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Patent number: 7887991Abstract: The present invention provides a polymer, having a high sensitivity, a high degree of resolution, a good pattern configuration after exposure, and in addition an excellent etching resistance, suitable as a base resin for a positive resist composition, especially for a chemically amplified positive resist composition; a positive resist composition using the polymer; and a patterning process. The positive resist composition of the present invention is characterized in that it contains at least, as a base resin, a polymer whose hydrogen atom of a phenolic hydroxide group is substituted by an acid labile group represented by the following general formula (1).Type: GrantFiled: January 22, 2009Date of Patent: February 15, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Takanobu Takeda
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Patent number: 7883826Abstract: A radiation-sensitive composition and negative-working imagable element includes a polymeric binder that has a hydrophobic backbone and pendant salt groups that comprise a cation covalently attached to the hydrophobic backbone and a boron-containing anion forming a salt with the cation. The use of these particular polymers provides fast digital speed (high imaging sensitivity) and good printability (good shelf-life) even when the preheat step normally used between exposure and development, is omitted.Type: GrantFiled: December 7, 2006Date of Patent: February 8, 2011Assignee: Eastman Kodak CompanyInventors: Scott A. Beckley, Ting Tao, Jianbing Huang
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Patent number: 7829259Abstract: A resin for photoresist compositions is disclosed with excellent resolution and line edge roughness characteristics. A photoresist composition and a method for forming a resist pattern using such a resin are also disclosed. The resin has a hydroxyl group bonded to a carbon atom at a polymer terminal, and the carbon atom in the ?-position to the hydroxyl group has at least one electron attractive group.Type: GrantFiled: February 4, 2009Date of Patent: November 9, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Masaru Takeshita, Shogo Matsumaru, Hiroaki Shimizu
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Patent number: 7824837Abstract: The present invention relates to a positive bottom photoimageable antireflective coating composition which is capable of being developed in an aqueous alkaline developer, wherein the antireflective coating composition comprises a polymer comprising at least one recurring unit with a chromophore group and one recurring unit with a hydroxyl and/or a carboxyl group, a vinyl ether terminated crosslinking agent, and optionally, a photoacid generator and/or an acid and/or a thermal acid generator. The invention further relates to a process for using such a composition.Type: GrantFiled: October 22, 2007Date of Patent: November 2, 2010Assignee: AZ Electronic Materials USA Corp.Inventors: Hengpeng Wu, Mark O. Neisser, Shuji S Ding-Lee, Aritaka Hishida, Joseph E. Oberlander, Medhat E. Toukhy
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Patent number: 7824836Abstract: A photosensitive composition contains: a compound capable of generating an acid upon irradiation with actinic rays or radiation; a basic compound represented by the formula (I-a) as defined herein; a basic compound represented by the formula (I-b) as defined herein; and a surfactant represented by the formula (II) as defined herein.Type: GrantFiled: August 30, 2007Date of Patent: November 2, 2010Assignee: FUJIFILM CorporationInventor: Hideaki Tsubaki
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Patent number: 7820360Abstract: There are provided a polymer compound which can form a resist pattern with excellent resolution, and a negative resist composition containing the polymer compound and a resist pattern-forming method thereof. The present invention is a polymer compound containing a structural unit (a0) represented by a general formula (a0-1) shown below. (wherein, R represents a hydrogen atom, a halogen atom, an alkyl group or a halogenated alkyl group; and R0 represents an alkyl group containing a hydroxyl group.) Also, the present invention is a negative resist composition, including: an alkali soluble resin component (A), an acid generator component (B) that generates acid upon exposure, and a cross-linking agent (C), wherein the alkali soluble resin component (A) contains a polymer compound (A1) having a structural unit (a0) represented by the general formula (a0-1) shown above.Type: GrantFiled: August 17, 2006Date of Patent: October 26, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Jun Iwashita, Ayako Kusaka
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Patent number: 7812194Abstract: 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: GrantFiled: August 30, 2006Date of Patent: October 12, 2010Assignee: FUJIFILM CorporationInventors: Kunihiko Kodama, Toshiaki Aoai
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Patent number: 7790351Abstract: A positive resist composition comprising: (A) a resin showing an increase in the solubility in an alkali developer by the action of an acid; (B) a compound being capable of generating an acid when irradiated with an actinic ray or a radiation; (C) a resin having a silicon-containing repeating unit of a specific structure and being stable to acids but insoluble in an alkali developer; and (D) a solvent; and a pattern making method using the same.Type: GrantFiled: January 30, 2009Date of Patent: September 7, 2010Assignee: FUJIFILM CorporationInventors: Toshiaki Fukuhara, Shinichi Kanna, Hiromi Kanda
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Patent number: 7785766Abstract: A photo-curable resin composition comprising a silphenylene-bearing polymer having a Mw of 3,000-500,000 can be processed to form patterned films having a widely varying thickness from submicron to more than 20 ?m. The cured films have good adhesion to substrates, heat resistance, electrical insulation and chemical resistance.Type: GrantFiled: January 30, 2008Date of Patent: August 31, 2010Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hideto Kato, Satoshi Asai
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Patent number: 7776505Abstract: The present invention addresses many of the current limitations in sub-100 nm lithographic techniques by providing novel resists that achieve high sensitivity, high contrast, high resolution, and high dry-etch resistance for pattern transfer to a substrate. In one embodiment, the present invention provides a polymeric resist comprising an adamantyl component and a photoacid generating component.Type: GrantFiled: September 14, 2005Date of Patent: August 17, 2010Assignee: The University of North Carolina at CharlotteInventor: Kenneth E. Gonsalves
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Patent number: 7776512Abstract: 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: GrantFiled: January 29, 2009Date of Patent: August 17, 2010Assignee: FUJIFILM CorporationInventors: Kunihiko Kodama, Toshiaki Aoai
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Patent number: 7771916Abstract: The present invention provides a polymerizable composition comprising (A) a compound represented by the following formula (I), (B) an infrared absorbent, and (C) a compound having at least one addition-polymerizable ethylenically unsaturated bond, and a negative planographic printing plate precursor having a recording layer containing the polymerizable composition. In the formula (I), R1, R2, R3, R4, R5, and R6 each independently represent a hydrogen atom or a monovalent organic group; and X? represents an anion.Type: GrantFiled: July 29, 2005Date of Patent: August 10, 2010Assignee: FUJIFILM CorporationInventors: Yoshinori Taguchi, Kazuhiro Fujimaki
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Patent number: 7749679Abstract: 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: December 21, 2006Date of Patent: July 6, 2010Assignee: FUJIFILM CorporationInventors: Kenji Wada, Kunihiko Kodama
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Patent number: 7745093Abstract: In the present invention, in a water soluble resin composition for use in a method for pattern formation in which a covering layer is provided on a resist pattern formed of a radiation-sensitive resin composition capable of coping with ArF exposure to increase the width of the resist pattern and thus to realize effective formation of higher density trench or hole pattern, the size reduction level of the resist pattern layer can be further increased as compared with that in the prior art technique, and, in addition, the size reduction level dependency of the coarse-and-fine resist pattern can be reduced. A method for pattern formation using the water soluble resin composition is also provided. The water soluble resin composition which is usable for the method for pattern formation applicable to ArF excimer laser irradiation comprises a water soluble resin, an acid generating agent capable of generating an acid upon heating, a surfactant, a crosslinking agent, and a water-containing solvent.Type: GrantFiled: April 8, 2005Date of Patent: June 29, 2010Inventors: Takeshi Nishibe, Sung Eun Hong, Yusuke Takano, Tetsuo Okayasu
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Patent number: 7741380Abstract: The invention provides (1) an ink composition including a polymerization initiator and at least one compound selected from the group consisting of (meth)acrylic acid and monofunctional (meth)acrylic acid esters and amides each having a carboxy group in the molecule, (2) an ink composition including a polymerization initiator, at least one compound selected from the group consisting of (meth)acrylic acid and monofunctional (meth)acrylic acid esters and amides each having a carboxy group in the molecule, and a monofunctional (meth)acrylic acid ester or amide having an alkylene oxide repeating unit in the molecule, and (3) an ink composition including a polymerization initiator and a monofunctional (meth)acrylic acid ester or amide having a basic group in the molecule; and an ink jet recording method, a method for producing a planographic printing plate and a planographic printing plate produced by the method for producing a planographic printing plate using the above-mentioned ink compositions.Type: GrantFiled: September 27, 2006Date of Patent: June 22, 2010Assignee: FUJIFILM CorporationInventor: Ippei Nakamura
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Patent number: 7709178Abstract: New photoresists for use during the production of semiconductor and MEMS devices are provided. The primer layer preferably comprises a silane dissolved or dispersed in a solvent system. The photoresist layer includes a first polymer prepared from a styrene and an acrylonitrile, and a second polymer comprising epoxy-containing monomers (and preferably phenolic-containing monomers). The photoresist layer comprises a photoacid generator, and is preferably negative-acting.Type: GrantFiled: April 17, 2007Date of Patent: May 4, 2010Assignee: Brewer Science Inc.Inventors: Xing-Fu Zhong, Tony D. Flaim, Jyoti Malhotra
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Patent number: 7704668Abstract: The invention provides positive-acting chemically-amplified photoresist compositions that can provide excellent lithographic performance as well as significantly enhanced storage stability. In one aspect, photoresist compositions are provided that comprise a solvent that is free of hydroxy groups (i.e. non-hydroxylic solvent), a resin binder and a photoactive compound that exhibits enhanced and long-term solubility in the solvent. In a further aspect, resists are provided that are formulated in a hydroxyl-containing solvent such as ethyl lactate and that contains a sulfonium salt photoactive compound that includes a sulfonate counter anion that can provide enhanced storage stability for the resist.Type: GrantFiled: August 4, 1998Date of Patent: April 27, 2010Assignee: Rohm and Haas Electronic Materials LLCInventors: James F. Cameron, James Michael Mori, George W. Orsula, Guangyu Xu, Yoshihiro Yamamoto
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Patent number: 7695890Abstract: New photoresists for use during the production of semiconductor and MEMS devices are provided. The primer layer preferably comprises a silane dissolved or dispersed in a solvent system. The photoresist layer includes copolymers prepared from styrene, acrylonitrile, and epoxy-containing monomers. The photoresist layer comprises a photoacid generator, and is preferably negative-acting.Type: GrantFiled: September 6, 2006Date of Patent: April 13, 2010Assignee: Brewer Science Inc.Inventors: Xing-Fu Zhong, Jyoti K. Malhotra, Chenghong Li
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Patent number: 7687223Abstract: There is provided an underlayer coating forming composition for lithography for forming an underlayer coating having a high dry etching rate compared with photoresist, causing no intermixing with the photoresist, and excellent in property of filling hole on the semiconductor substrate, which is used in lithography process of manufacture of semiconductor device. The composition comprises a cyclodextrin compound that 10% to 90% of total number of hydroxy groups in cyclodextrin is converted into an ether or ester group, a crosslinking compound, a crosslinking catalyst and a solvent.Type: GrantFiled: October 25, 2005Date of Patent: March 30, 2010Assignee: Nissan Chemical Industries, Ltd.Inventors: Satoshi Takei, Tetsuya Shinjo, Keisuke Hashimoto
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Patent number: 7678528Abstract: The present invention relates to novel photoacid generators.Type: GrantFiled: February 16, 2006Date of Patent: March 16, 2010Assignee: AZ Electronic Materials USA Corp.Inventors: M. Dalil Rahman, Munirathna Padmanaban
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Patent number: 7678529Abstract: A multilayer resist process comprises forming in sequence an undercoat film, an intermediate film, and a photoresist film on a patternable substrate, and effecting etching in multiple stages. A silicon-containing film forming composition is useful in forming the intermediate film serving as an etching mask, comprising a silicon-containing polymer obtained through hydrolytic condensation of at least one Si—Si bond-containing silane compound having formula: R(6-m)Si2Xm wherein R is a monovalent hydrocarbon group, X is alkoxy, alkanoyloxy or halogen, and m is 3 to 6. The composition allows the overlying photoresist film to be patterned to a satisfactory profile and has a high etching selectivity relative to organic materials.Type: GrantFiled: November 8, 2006Date of Patent: March 16, 2010Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsutomu Ogihara, Takeshi Asano, Motoaki Iwabuchi, Takafumi Ueda
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Patent number: 7670749Abstract: A method for the formation of a patterned resist layer on a substrate surface by patternwise irradiation with actinic radiation. The first step of the method is formation of a coating layer comprising a substituted triphenylene compound having a diameter of between 1 and 3 nm, a sensitizer which increases the sensitivity of the exposed layer to the actinic radiation used in a subsequent irradiation step and a cross-linker on the substrate surface. Subsequently the coating layer is irradiated patternwise, and unirradiated areas of the coating layer are removed. A resist material comprising a solution of: (i) as the principal resist material a triphenylene derivative having a diameter of from 1 to 3 rim, (ii) a sensitizer which increases the sensitivity of the resist material to actinic radiation, and (iii) a cross-linker capable of cross-linking molecules of the triphenyl derivative, the cross-linker optionally being constituted by a moiety attached to the triphenylene derivative.Type: GrantFiled: September 19, 2005Date of Patent: March 2, 2010Assignee: The University of BirminghamInventors: Richard Edward Palmer, Alex Robinson, Jon Andrew Preece
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Patent number: 7651830Abstract: Provided is an article that comprises a substrate comprising an acid-etchable layer, a water-soluble polymer matrix, and a photoacid generator. Also provided is a method for patterning that can provide patterned layers that can be used to form electroactive devices.Type: GrantFiled: June 1, 2007Date of Patent: January 26, 2010Assignee: 3M Innovative Properties CompanyInventors: Wayne S Mahoney, Steven D. Theiss
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Patent number: 7632622Abstract: Hardmask compositions having antireflective properties useful in lithographic processes, methods of using the same, and semiconductor devices fabricated by such methods, are provided. Antireflective hardmask compositions of the invention include: (a) a polymer mixture including a first polymer that includes one or more of the following monomeric units wherein A is a bivalent radical selected from the group consisting of carbonyl, oxy, alkylene, fluoroalkylene, phenyldioxy, and any combination thereof; R1 and R2 are each independently a bivalent radical selected from the group consisting of an alkylene, an arylene, and any combination thereof; and x, y, and z are 0 or integers; and a second polymer including an aryl group; (b) a crosslinking component; and (c) an acid catalyst.Type: GrantFiled: December 12, 2005Date of Patent: December 15, 2009Assignee: Cheil Industries, Inc.Inventors: Dong Sun Uh, Ji Young Jung, Jae Min Oh, Chang Il Oh, Do Hyeon Kim
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Patent number: 7629106Abstract: 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: GrantFiled: October 16, 2006Date of Patent: December 8, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Koji Hasegawa, Youichi Ohsawa, Seiichiro Tachibana
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Patent number: 7625687Abstract: 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: GrantFiled: June 30, 2004Date of Patent: December 1, 2009Assignee: Dow Corning CorporationInventors: Sanlin Hu, Eric Scott Moyer, Sheng Wang, David Lee Wyman
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Patent number: 7622243Abstract: The present invention is a photosensitive element including a support and a photosensitive resin composition layer composed of a photosensitive resin composition containing (A) a binder polymer, (B) a photopolymerizable compound, and (C) a photopolymerization initiator, wherein, the photosensitive resin composition contains a thioxanthone-based compound represented by the following general formula (I) as the component (C), and when the parts by weight of the thioxanthone-based compound relative to 100 parts by weight for the total weight of the component (A) and the component (B) is taken to be P, and the film thickness of the photosensitive resin composition layer is taken to be Q (?m), then R, which is the product of P and Q, satisfies the condition of the following formula (1). In the following general formula (I), R1to R8 represent a hydrogen atom, halogen atom or hydrocarbon group. 25.5?R?79.Type: GrantFiled: September 17, 2004Date of Patent: November 24, 2009Assignee: Hitachi Chemical Company, Ltd.Inventors: Takashi Kumaki, Masahiro Miyasaka, Yasuhisa Ichihashi, Toshiki Ito, Makoto Kaji
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Patent number: 7611817Abstract: Novel aromatic sulfonium salt compounds of general formula (I), photo-acid generators comprising the same, and photo-polymerizable compositions containing the same, capable of providing stereolithographic resin compositions which do not suffer from the hindrance to curing by oxygen, can easily give shaped articles having desired sizes by virtue of the high accuracy thereof in curing, can attain a satisfactory curing depth owing to the high sensitivity thereof for radiant energy and can be employed for wide usage, such as photoresist and ink for foods-packing medium, since the release of benzene is suppressed; and a stereolithographic process, using said stereolithographic resin composition.Type: GrantFiled: September 25, 2003Date of Patent: November 3, 2009Assignee: Adeka CorporationInventors: Tetsuyuki Nakayashiki, Hiroyuki Tachikawa
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Patent number: 7608381Abstract: The positive resist composition of the present invention is a polymer compound comprising at least one constituent unit (a1) selected from the group consisting of constituent units represented by the following general formulas (1) and (1)?, a constituent unit (a2) derived from an (?-lower alkyl)acrylate ester having a lactone-containing monocycle or a polycyclic group, and a constituent unit (a3) which is a constituent unit other than the constituent unit (a1) and the constituent unit (a2) and is derived from an (?-lower alkyl)acrylate ester which has an aliphatic cyclic group-containing non-acid dissociable dissolution inhibiting group and does not have a polar group: wherein R represents a hydrogen atom, a fluorine atom, a lower alkyl group having 20 or less carbon atoms, or a fluorinated lower alkyl group having 20 or less carbon atoms, R1 represents at most 20-membered cyclic group which may have a substituent, n represents 0 or an integer of 1 to 5, and m represents 0 or 1.Type: GrantFiled: June 10, 2005Date of Patent: October 27, 2009Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yohei Kinoshita, Takeshi Iwai
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Patent number: 7601482Abstract: The present invention relates to a negative photoresist composition comprising, a) at least one alkali-soluble polymer, where the polymer comprises at least one unit of structure 1, where, R? is selected independently from hydrogen, (C1-C4)alkyl, chlorine, bromine and m is an integer from 1 to 4; b) at least one monomer of structure 1, where, W is a multivalent linking group, R1 to R6 are independently selected from hydrogen, hydroxyl, (C1-C20) alkyl and chlorine, X1 and X2 are independently oxygen or N—R7, where R7 is hydrogen or (C1-C20) alkyl, and n is and integer equal to or greater than 1, and c) at least one photoinitiator. The invention also relates to a process for imaging the negative photoresist composition.Type: GrantFiled: March 28, 2006Date of Patent: October 13, 2009Assignee: AZ Electronic Materials USA Corp.Inventors: Georg Pawlowski, Chunwei Chen, Joseph Oberlander, Robert Plass
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Patent number: 7592123Abstract: A resin for photoresist compositions is disclosed with excellent resolution and line edge roughness characteristics. A photoresist composition and a method for forming a resist pattern using such a resin are also disclosed. The resin has a hydroxyl group bonded to a carbon atom at a polymer terminal, and the carbon atom in the ?-position to the hydroxyl group has at least one electron attractive group.Type: GrantFiled: June 2, 2004Date of Patent: September 22, 2009Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Masaru Takeshita, Shogo Matsumaru, Hiroaki Shimizu
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Patent number: RE40964Abstract: 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: GrantFiled: September 17, 2003Date of Patent: November 10, 2009Assignee: Sumitomo Chemical Company, LimitedInventors: Masumi Suetsugu, Takehiro Kusumoto, Naoki Takeyama, Masanori Shinada