Binder Containing Patents (Class 430/905)
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Patent number: 7364833Abstract: The invention relates to a photoresist composition for an organic layer for a liquid crystal display, which may be used for a large-scale substrate, a spin-less coating method using the composition, a method for fabricating an organic layer pattern, and a liquid crystal display having the organic layer pattern. In particular, the liquid crystal display photoresist composition comprises an organic polymer resin having an average molecular weight in the range of about 2,000 to about 20,000, a mixed solvent of ethylene diglycol methylethyl ether (EDM) and a solvent having a vapor pressure lower than the EDM, and a photosensitizer.Type: GrantFiled: May 24, 2005Date of Patent: April 29, 2008Assignee: Samsung Electronics Co., LtdInventors: Yeong-beom Lee, Seon-su Sin
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Patent number: 7358028Abstract: The present invention provides a chemical amplification type positive photoresist composition which is excellent in storage stability as a resist solution in a bottle. A novolak resin or a hydroxystyrenic resin is reacted with a crosslinking agent to give a slightly alkali-soluble or alkali-insoluble resin having such a property that solubility in an aqueous alkali solution is enhanced in the presence of an acid, which is then dissolved in an organic solvent, together with (B) a compound generating an acid under irradiation with radiation to obtain a chemical amplification type positive photoresist composition wherein the content of an acid component is 10 ppm or less.Type: GrantFiled: May 19, 2004Date of Patent: April 15, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Kenji Maruyama, Masaki Kurihara, Ken Miyagi, Satoshi Niikura, Satoshi Shimatani, Masahiro Masujima, Kazuyuki Nitta, Toshihiro Yamaguchi, Kousuke Doi
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Patent number: 7358029Abstract: A photoresist composition including a polymer, a photoacid generator and a dissolution modification agent, a method of forming an image using the photoresist composition and the dissolution modification agent composition. The dissolution modification agent is insoluble in aqueous alkaline developer and inhibits dissolution of the polymer in the developer until acid is generated by the photoacid generator being exposed to actinic radiation, whereupon the dissolution modifying agent, at a suitable temperature, becomes soluble in the developer and allows the polymer to dissolve in the developer. The DMAs are glucosides, cholates, citrates and adamantanedicarboxylates protected with acid-labile ethoxyethyl, tetrahydrofuranyl, and angelicalactonyl groups.Type: GrantFiled: September 29, 2005Date of Patent: April 15, 2008Assignee: International Business Machines CorporationInventors: Robert David Allen, Phillip Joe Brock, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D. Truong
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Patent number: 7351515Abstract: A positive resist composition includes: (A) a resin capable of increasing a solubility thereof in an alkali developer by an action of an acid; (B) a compound capable of generating a sulfonic acid represented by the following formula (I) upon irradiation with one of an actinic ray and a radiation; and (C1) at least one of an amine compound having at least an aliphatic hydroxyl group in a molecule and an amine compound having at least an ether bond in a molecule: A1A2-SO3H)n ??(I) wherein A1 represents an n-valent linking group, A2 represents a single bond or a divalent aliphatic group, and A2's each may be the same or different, provided that at least one group represented by A1 or A2 contains a fluorine atom, and n represents an integer of from 2 to 4.Type: GrantFiled: September 16, 2004Date of Patent: April 1, 2008Assignee: FUJIFILM CorporationInventors: Shoichiro Yasunami, Kenji Wada, Kunihiko Kodama, Kenichiro Sato
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Patent number: 7344820Abstract: The present invention relates to a chemically amplified polymer having a pendent group with dicyclohexyl bonded thereto, a process for the preparation thereof, and a resist composition comprising it, and more particularly, to a novel (meth)acrylic or norbornene carboxylate compound with dicyclohexyl bonded thereto, a process for the preparation thereof, a chemically amplified polymer synthesized therewith, and a positive photoresist composition for ArF comprising said polymer, with high resolution and excellent etching resistance.Type: GrantFiled: November 19, 2002Date of Patent: March 18, 2008Assignee: DongJin Semichem Co., Ltd.Inventors: Eun-Kyung Son, Jae-Hyun Kang, Deog-Bae Kim, Jae-Hyun Kim
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Patent number: 7341817Abstract: A photosensitive composition comprising a compound capable of generating a specific sulfonic acid upon irradiation with actinic rays or a radiation; a compound capable of generating a specific sulfonic acid upon irradiation with an actinic ray or a radiation; and a pattern forming method using a photosensitive composition comprising a compound capable of generating a specific sulfonic acid upon irradiation with an actinic ray or a radiation.Type: GrantFiled: November 22, 2004Date of Patent: March 11, 2008Assignee: FUJIFILM CorporationInventors: Kenji Wada, Kunihiko Kodama
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Patent number: 7341816Abstract: A photoresist composition encompassing a polymer having at least one polycyclic olefin repeat unit having a desired exo mole percent is provided, where the repeat unit is derived from a polycyclic olefin monomer having the desired exo mole percent. Such polymers having such repeat units having a desired exo mole percent offer control of differential dissolution rate and hence provide enhanced imaging properties. Exemplary monomers having a desired exo mole percent are also provided.Type: GrantFiled: February 20, 2004Date of Patent: March 11, 2008Assignees: Promerus, LLC, International Business Machines CorporationInventors: Larry F. Rhodes, Chun Chang, Leah J. Langsdorf, Howard A. Sidaway, Hiroshi Ito
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Patent number: 7341818Abstract: The disclosed invention relates to novel norborne-type monomers containing pendent lactone or sultone groups. The invention also relates to norborne-type polymers and copolymers containing pendent lactone or sultone groups. These polymers and copolymers are useful in making photoimagable materials. The photoimagable materials are particularly suitable for use in photoresist compositions useful in 193 and 157 nm photolithography.Type: GrantFiled: January 10, 2005Date of Patent: March 11, 2008Assignee: Promerus LLCInventors: Xiaoming Wu, Larry F. Rhodes, Lawrence Seger
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Patent number: 7338755Abstract: The photosensitive composition of the invention contains a polymer material having a group having a structure represented by following general formula (2), and a photo acid generator generating acid with an ultraviolet ray or an ionizing radiation wherein m represents an integer of 0 or more.Type: GrantFiled: May 22, 2007Date of Patent: March 4, 2008Assignee: Kabushiki Kaisha ToshibaInventor: Satoshi Saito
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Patent number: 7338745Abstract: Positive-working imageable elements comprise a radiation absorbing compound and inner and outer layers on a substrate having a hydrophilic surface. The inner layer comprises a polymeric material that is removable using an alkaline developer and comprises a backbone and attached groups represented by the following Structure Q: wherein L1, L2, and L3 independently represent linking groups, T1, T2, and T3 independently represent terminal groups, and a, b, and c are independently 0 or 1. The imageable elements have improved resistance to development and printing chemicals and solvents.Type: GrantFiled: January 23, 2006Date of Patent: March 4, 2008Assignee: Eastman Kodak CompanyInventors: Kevin B. Ray, Ting Tao, Scott A. Beckley
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Patent number: 7335454Abstract: A positive resist composition comprising (A) a fluorine group-containing resin, which has a structure substituted with a fluorine atom in the main chain and/or side chain of polymer skeleton and a group that is decomposed by the action of an acid to increase solubility in an alkali developer and (B) an acid generator capable of generating an acid upon irradiation of an actinic ray or radiation, and the acid generator of (B) is a compound selected from a sulfonium salt containing no aromatic ring and a compound having a phenacylsulfonium salt structure.Type: GrantFiled: December 12, 2002Date of Patent: February 26, 2008Assignee: FUJIFILM CorporationInventors: Shinichi Kanna, Kazuyoshi Mizutani, Kunihiko Kodama, Tomoya Sasaki
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Patent number: 7335458Abstract: A chemically amplified positive resist composition is provided comprising (A) a resin containing acid labile groups other than acetal type which changes its solubility in an alkaline developer as a result of the acid labile groups being eliminated under the action of acid and (B) specific sulfonium salts as a photoacid generator. The composition is improved in resolution and focus latitude, minimized in line width variation and profile degradation even on prolonged PED, improved in pattern profile after development, minimized in pattern feature size variation within the wafer plane by uneven development and thus best suited in the deep-UV lithography.Type: GrantFiled: February 15, 2006Date of Patent: February 26, 2008Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Kazunori Maeda, Satoshi Watanabe
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Patent number: 7335457Abstract: A positive-tone radiation-sensitive resin composition containing an anthracene-based carboxylic acid component with low sublimation properties and excellent compatibility with other components is provided. The composition exhibits optimum controllability of radiation transmittance as a chemically amplified positive-tone resist effectively responding to active radiation, particularly to deep ultraviolet rays, effectively controlling line width variation in resist patterns due to fluctuation in the resist film thickness on a highly refractive substrate, and exhibiting excellent focal depth allowance. The composition comprises (A) an anthracene derivative of the following formula (1), (B) a photoacid generator comprising a sulfonimide compound, and, (C) a resin containing an acid-dissociable group, wherein R1 is a hydrogen atom or a monovalent organic group, R2 is a monovalent organic group, e is an integer of 0-3, and f is an integer of 0-8.Type: GrantFiled: September 27, 2005Date of Patent: February 26, 2008Assignee: JSR CorporationInventors: Daisuke Shimizu, Tomoki Nagai, Yuuji Yada, Kentarou Gotou
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Patent number: 7329478Abstract: To provide a chemical amplification type positive photoresist composition, which has high sensitivity, high heat resistance and high resolution (high contrast) and is capable of suppressing an undulation phenomenon, and a method for formation of a resist pattern, a chemical amplification type positive photoresist composition comprising (A) an alkali soluble resin comprising a hydroxystyrene constituent unit (a1) and a styrene constituent unit (a2), (B) a crosslinking agent, (C) a photo acid generator, and an organic solvent is prepared and a resist pattern is formed by using the same.Type: GrantFiled: May 20, 2004Date of Patent: February 12, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yusuke Nakagawa, Shinichi Hidesaka, Kenji Maruyama, Satoshi Shimatani, Masahiro Masujima, Kazuyuki Nitta
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Patent number: 7326515Abstract: There is provided a positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.Type: GrantFiled: December 7, 2004Date of Patent: February 5, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
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Patent number: 7326510Abstract: Mixed carbocycle derivatives containing at least two carbocycles per molecule from the group of anthracenes, adamantanes and steroids with functionalized carbon chains are synthesized and used as modifiers of resist properties and especially etch resistance enhancement and absorption characteristics. These derivatives are characterized by formulas I-V, where A and R may be an anthryl- and/or an adamantyl- and/or a steroid moiety. Methods for the preparation of the above compounds are disclosed.Type: GrantFiled: October 31, 2002Date of Patent: February 5, 2008Inventors: Evangelos Gogolides, Panagiotis Argitis, Elias Andrea Couladouros, Veroniki Petrou Vidali, Maria Vasilopoulou, George Cordoyiannis
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Patent number: 7326514Abstract: Resist compositions containing silicon, boron, or both silicon and boron may be used with ultra-violet lithography processes and extreme ultra-violet (EUV) lithography processes to increase the reactive ion etch resistance of the resist compositions, improve transmission of the resist materials, and to dope substrates.Type: GrantFiled: March 12, 2004Date of Patent: February 5, 2008Assignees: Cornell Research Foundation, Inc., University of Wisconsin-MadisonInventors: Junyan Dai, Christopher K. Ober, Lin Wang, Franco Cerrina, Paul Nealey
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Patent number: 7326518Abstract: Chemically-amplified positive photoresist compositions are provided that contain a resin that comprises acetal and alicyclic groups. Photoresists of the invention can exhibit notably enhanced lithographic properties. Preferred photoresists of the invention comprise one or more photoacid generator compounds and one or more phenolic resins comprise one or more photoacid-labile acetal groups and one or more alicyclic groups such as adamantyl.Type: GrantFiled: November 23, 2005Date of Patent: February 5, 2008Assignee: Rohm and Haas Electronic Materials LLCInventors: James F. Cameron, Dong Woo Lee, Peter Trefonas, III, Gary J. Swanson, Jin Wuk Sung
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Patent number: 7323287Abstract: There is provided a positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.Type: GrantFiled: February 2, 2006Date of Patent: January 29, 2008Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
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Patent number: 7323286Abstract: A photosensitive composition, comprises (A) a sulfonium salt represented by formula (I); wherein Y1, Y2 and Y3 each independently represents a nitrogen-containing heteroaryl group, an alkyl group, a cycloalkyl group, an aryl group or an alkenyl group, at least one of Y1, Y2 and Y3 represents a nitrogen-containing heteroaryl group, and at least two of Y1, Y2 and Y3 may combine with each other to form a ring; Xn? represents an n-valent non-nucleophilic anion; and n represents an integer of 1 to 3.Type: GrantFiled: April 19, 2005Date of Patent: January 29, 2008Assignee: FUJIFILM CorporationInventor: Kunihiko Kodama
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Patent number: 7323284Abstract: A negative type radiation sensitive resin composition comprising: (A) an alkali-soluble resin containing the polymerized unit of a polymerizable unsaturated compound having a phenolic hydroxyl group and having a weight average molecular weight of 4,100 to 20,000 and a weight average molecular weight/number average molecular weight ratio of more than 1.25 to not more than 2.00; (B) a radiation sensitive acid generating agent; and (C) an acid crosslinking agent. This composition can be used with an alkali developer having a normal concentration, can form a high-resolution rectangular line-and-space resist pattern, and provides a chemically amplified negative type resist which is free from a resist pattern defect (bridging or chip line) after development and has excellent sensitivity, developability and dimensional fidelity.Type: GrantFiled: June 17, 2002Date of Patent: January 29, 2008Assignee: JSR CorporationInventors: Toshiyuki Kai, Daigo Ichinohe
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Patent number: 7316885Abstract: There are provided a method of forming a resist pattern that enables the resist pattern to be formed with good control of the pattern size, as well as a positive resist composition used in the method, and a layered product formed using the positive resist composition. In the above method a positive resist composition comprising a resin component (A), which contains a structural unit (a1) derived from a (meth)acrylate ester represented by a general formula (I) shown below, and displays increased alkali solubility under action of acid, and an acid generator component (B) that generates acid on exposure is applied to a substrate, a prebake is conducted, the resist composition is selectively exposed, post exposure baking (PEB) is conducted, alkali developing is then used to form a resist pattern, and the pattern size of the thus produced resist pattern is then narrowed by heat treatment.Type: GrantFiled: December 1, 2003Date of Patent: January 8, 2008Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Hideo Hada, Miwa Miyairi, Naotaka Kubota, Takeshi Iwai
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Patent number: 7316889Abstract: There is provided a positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.Type: GrantFiled: February 2, 2006Date of Patent: January 8, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
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Patent number: 7316888Abstract: There is provided a positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.Type: GrantFiled: February 2, 2006Date of Patent: January 8, 2008Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
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Patent number: 7316884Abstract: A 5-methylene-1,3-dioxolan-4-one derivative and a monomer and copolymer thereof and a resist composition containing the polymer or copolymer where the 5-methylene-1,3 -dioxolan-4-one derivative is of formula (1): wherein R1 represents a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms, or a linear or branched alkyl group containing 1 to 6 carbon atoms which has a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms as a substituent; R2 represents a hydrogen atom, or a linear or branched alkyl group containing 1 to 6 carbon atoms; or R1 and R2 represent a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms together with the carbon atom to which they are bound, provided that the alkyl group and the bridged cyclic hydrocarbon group may have at least one substituent selected from a group consisting of a linear or branched alkyl group containing 1 to 6 carbon atoms which may be optionally substituted, a hydroxy group, a carboxy group, an acyl group containing 2 to 6 carType: GrantFiled: October 22, 2002Date of Patent: January 8, 2008Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Ryuichi Ansai, Yoshihiro Kamon, Tadayuki Fujiwara, Hideaki Kuwano, Atsushi Ootake, Hikaru Momose
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Patent number: 7314699Abstract: The present invention relates to a radiation-sensitive mixture which contains an acrylate or methacrylate monomer and/or oligomer capable of free radical polymerization and having at least two acrylate and/or methacrylate groups and at least one photooxidizable group, a photoinitiator, an organic polymeric binder and a heptamethinecyanine dye acting as an IR-absorbing dye. It furthermore relates to a recording material comprising a substrate and a photopolymerizable layer and a process for the production of a printing plate from this recording material. The recording material is distinguished by suitable photosensitivity.Type: GrantFiled: April 29, 2003Date of Patent: January 1, 2008Assignee: Agfa Graphics NVInventor: Willi-Kurt Gries
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Patent number: 7314701Abstract: A positive tone radiation-sensitive resin composition comprising (A) a 1-substituted imidazole, (B) a photoacid generator, and (C-a) a resin protected by an acid-dissociable group, insoluble or scarcely soluble in alkali, but becoming soluble in alkali when the acid-dissociable group dissociates or (C-b) an alkali-soluble resin and an alkali solubility controller, and a negative tone radiation-sensitive resin composition comprising (A), (B), (D) an alkali-soluble resin, and (E) a compound that can crosslink the alkali-soluble resin in the presence of an acid. The radiation-sensitive resin composition of the present invention is a chemically amplified resist exhibiting high resolution and high storage stability as a composition, and suitable for microfabrication sensible to active radiations, for example, ultraviolet rays such as g-lines and i-lines, deep ultraviolet rays represented by a KrF excimer laser, ArF excimer laser, F2 excimer laser, and EUV excimer laser, and electron beams.Type: GrantFiled: October 7, 2003Date of Patent: January 1, 2008Assignee: JSR CorporationInventors: Kenichi Yokoyama, Fumihisa Miyajima, Tomoki Nagai, Eiji Yoneda
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Patent number: 7314703Abstract: In a pattern formation method, a resist film made of a chemically amplified resist material including a first polymer having hemiacetal or hemiketal is formed on a substrate. Then, with a liquid provided on the resist film, pattern exposure is performed by selectively irradiating the resist film with exposing light. After the pattern exposure, the resist film is developed so as to form a resist pattern made of the resist film.Type: GrantFiled: April 24, 2006Date of Patent: January 1, 2008Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Masayuki Endo, Masaru Sasago
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Patent number: 7312014Abstract: The present invention relates to a resist composition for practical use with high resolution, high sensitivity, superior pattern profile and no outgas in energy irradiation under high vacuum, suitable to an ultra-fine processing technology represented by use of electron beam and the like, and provides: (1) a resist composition comprising at least one kind of polymer containing, as components thereof, a monomer unit represented by the following general formula [1]: a monomer unit represented by the following general formula [2]: and a monomer unit represented by the following general formula [3]: at least one kind of compound to generate an acid by irradiation of radioactive ray, represented by the following general formula [4]; an organic basic compound; and a solvent, (2) the resist composition in accordance with (1), further containing a polymer unit represented by the following general formula [13]: and, (3) the resist composition in accordance with (1) and (2), further containing a compType: GrantFiled: June 21, 2002Date of Patent: December 25, 2007Assignee: Wako Pure Chemical Industries Ltd.Inventors: Tsuneaki Maesawa, Fumiyoshi Urano
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Patent number: 7312016Abstract: A chemically amplified positive resist composition comprising a specific 2,4,6-triisopropylbenzenesulfonate compound as a photoacid generator, a polymer which changes its solubility in an alkaline developer under the action of acid, and a basic compound has a high sensitivity, a high contrast of dissolution of resist film, a high resolution, and good storage stability.Type: GrantFiled: October 19, 2006Date of Patent: December 25, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Ryuji Koitabashi, Satoshi Watanabe, Youichi Ohsawa
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Patent number: 7309750Abstract: Cyanoadamantyl compounds, polymers that comprise polymerized units of such compounds, and photoresist compositions that comprise such polymers are provided. Preferred polymers of the invention are employed in photoresists imaged at wavelengths less than 250 nm such as 248 nm and 193 nm.Type: GrantFiled: March 8, 2005Date of Patent: December 18, 2007Assignee: Rohm and Haas Electronic Materials LLCInventors: Young C. Bae, Robert J. Kavanagh
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Patent number: 7303852Abstract: The invention provides a high-resolution resist material comprising an acid generator that has high sensitivity and high resolution with respect to high-energy rays of 300 nm or less, has small line-edge roughness, and is superior in heat stability and in shelf stability, and provides a pattern forming method that uses this resist material. The invention further provides a chemically amplified positive resist material comprising a base resin, an acid generator and a solvent in which the acid generator generates an alkylimidic acid containing a fluorine group, and provides a pattern forming method comprising a step of applying the resist material to the substrate, a step of performing exposure to a high-energy ray of a wavelength of 300 nm or less through a photomask following heat treatment, and a step of performing development by a developing solution following heat treatment.Type: GrantFiled: February 27, 2003Date of Patent: December 4, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Tomohiro Kobayashi, Youichi Ohsawa
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Patent number: 7297464Abstract: The present invention provides a radiation curing composition comprising (a): a siloxane resin, (b): a photoacid generator or photobase generator, and (c): a solvent capable of dissolving component (a), and (d): a curing acceleration catalyst.Type: GrantFiled: June 27, 2005Date of Patent: November 20, 2007Assignee: Hitachi Chemical Co., Ltd.Inventors: Haruaki Sakurai, Koichi Abe
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Patent number: 7291442Abstract: Image formation via photoinduced fluorescence changes in a polymeric medium with two-photon fluorescence readout of a multi-layer structure. Fluorophore-containing polymers, possessing one or more basic functional groups, underwent protonation in the presence of a photoinduced acid generator upon exposure to a broad-band UV light source or fast-pulsed red to near-IR laser irradiation. Solution studies demonstrated formation of monoprotonated and diprotonated species upon irradiation, each resulting in distinctly different absorption and fluorescence properties. The fluorescence of the original, neutral, fluorophore was reduced upon monoprotonation, leading to a concomitant increase in fluorescence at longer wavelengths due to the monoprotonated form, the basis for multichannel data readout.Type: GrantFiled: October 21, 2005Date of Patent: November 6, 2007Assignee: University of Central Florida Research Foundation, Inc.Inventor: Kevin D. Belfield
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Patent number: 7291441Abstract: A positive resist composition comprising: a resin that comprises a repeating unit including a specific norbornane lactone structure and a repeating unit including a specific alicyclic hydrocarbon structure, and that increases a solubility of the resin in an alkaline developer by an action of an acid; and a compound that generates an acid upon treatment with one of an actinic ray and radiation, and a pattern forming method utilizing the same.Type: GrantFiled: August 25, 2005Date of Patent: November 6, 2007Assignee: Fujifilm CorporationInventor: Kenichiro Sato
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Patent number: 7288363Abstract: A chemically amplified positive resist composition comprising a specific 2,4,6-triisopropylbenzenesulfonate compound as a photoacid generator, a polymer which changes its solubility in an alkaline developer under the action of acid, and a basic compound has a high sensitivity, a high contrast of dissolution of resist film, a high resolution, and good storage stability.Type: GrantFiled: April 14, 2005Date of Patent: October 30, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Ryuji Koitabashi, Satoshi Watanabe, Youichi Ohsawa
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Patent number: 7288359Abstract: A radiation-sensitive resin composition comprising (A) an acid-dissociable group-containing polysiloxane and (B) a photoacid generator containing trifluoromethane sulfonic acid or a compound which generates an acid of the following formula (I), wherein Rf individually represents a fluorine atom or a trifluoromethyl group, and Ra represents a hydrogen atom, a fluorine atom, a linear or branched alkyl group having 1-20 carbon atoms, or a linear or branched fluoroalkyl group having 1-20 carbon atoms, a substituted or unsubstituted monovalent cyclic hydrocarbon group having 3-20 carbon atoms, or a substituted or unsubstituted monovalent cyclic fluoro-hydrocarbon group having 3-20 carbon atoms. The radiation-sensitive resin composition of the present invention exhibits superior resolution, while maintaining high transparency to radiations and high dry etching resistance. The resin composition thus can greatly contribute to the lithography process that will become more and more minute in the future.Type: GrantFiled: December 4, 2002Date of Patent: October 30, 2007Assignee: JSR CorporationInventors: Haruo Iwasawa, Akihiro Hayashi, Tsutomu Shimokawa
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Patent number: 7285369Abstract: A positive resist composition comprising (A) a resin that increases solubility in an alkali developing solution by the action of an acid and (B-1) a compound having a structure represented by formula (I) defined in the specification.Type: GrantFiled: September 17, 2004Date of Patent: October 23, 2007Assignee: FUJIFILM CorporationInventor: Hyou Takahashi
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Patent number: 7282316Abstract: Provided are sulfonyldiazomethane compounds and photoacid generators suited for resist materials which generate less foreign matters after application, development and peeling, and in particular, are excellent in the pattern profile after the development; and resist materials and patterning process using them. Provided are sulfonyldiazomethane compounds represented by formula (1): Also provides are photoacid generators containing the sulfonyldiazomethane compounds, and a chemical amplification resist material comprising (A) a resin which changes its solubility in an alkali developer by action of an acid, and (B) a sulfonyldiazomethane compound of formula (1) capable of generating an acid by exposure to radiation. Provided is a patterning process comprising steps of applying the above-described resist material onto a substrate to form a coating, heating the coating, exposing the coating, and developing the exposed coating in a developer after an optional heat treatment.Type: GrantFiled: August 27, 2004Date of Patent: October 16, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Eiji Fukuda, Shigeo Tanaka
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Patent number: 7282318Abstract: The present invention relates to photoresist compositions for EUV and methods for forming photoresist patterns. More specifically, fine photoresist patterns: of less than 50 nm without collapse are formed with EUV (Extreme Ultraviolet) as an exposure light source by using a negative photoresist composition comprising a melamine derivative and polyvinylphenol.Type: GrantFiled: June 24, 2004Date of Patent: October 16, 2007Assignee: Hynix Semiconductor Inc.Inventor: Jae Chang Jung
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Patent number: 7279256Abstract: Photoresist polymers and photoresist compositions are disclosed. A photoresist polymer comprising a polymerization repeating unit represented by Formula I is less sensitive to change in the amount of energy due to its higher active energy than that of a conventional photoresist polymer. As a result, a phenomenon where the portion of the pattern for the storage electrode contact region that receives relatively large amount of light becomes too thin is avoided when the device isolation film pattern is formed, and wherein pattern collapse caused by a high aspect ratio due to high etching resistance is prevented or avoided. wherein R1–R10, a, b, c and d are as defined in the description.Type: GrantFiled: May 9, 2005Date of Patent: October 9, 2007Assignee: Hynix Semiconductor Inc.Inventor: Min Seok Son
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Patent number: 7279265Abstract: A positive resist composition comprising (A) a resin capable of increasing its solubility in an alkali developer under action of an acid, wherein the resin contains a repeating unit originated in an acrylic acid ester derivative in an amount of 50 to 100 mol % based on all repeating units and has a repeating unit having a specific lactone structure and a repeating unit having a monohydroxyadamantane or dihydroxyadamantane structure, (B) a compound of generating an acid upon irradiation with actinic rays or radiation, and (C) an organic solvent, and a pattern formation method using the composition.Type: GrantFiled: March 18, 2004Date of Patent: October 9, 2007Assignee: FujiFilm CorporationInventors: Makoto Momota, Hajime Nakao
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Patent number: 7279266Abstract: A photosensitive composition comprising: (A) a polymerizable compound represented by the following formula (I): A—{O—[(CH(—R1)CH(—R2))m—O]n—C(?O)—C(—R3)?CH2}p??(I) wherein R1, R2and R3 each represents a hydrogen atom or a methyl group, A represents a polyhydric alcohol residue or a polyhydric phenol residue, m represents an integer of from 1 to 6, n represents an integer of from 1 to 20, and p represents an integer of from 1 to 6; (B) an infrared absorber; and (C) an onium salt.Type: GrantFiled: September 23, 2004Date of Patent: October 9, 2007Assignee: FUJIFILM CorporationInventors: Hiromitsu Yanaka, Takahiro Goto
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Patent number: 7270935Abstract: Cyanoadamantyl compounds, polymers that comprise polymerized units of such compounds, and photoresist compositions that comprise such polymers are provided. Preferred polymers of the invention are employed in photoresists imaged at wavelengths less than 250 nm such as 248 nm and 193 nm.Type: GrantFiled: March 8, 2005Date of Patent: September 18, 2007Assignee: Rohm and Haas Electronic Materials LLCInventors: Young C. Bae, Robert J. Kavanagh
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Patent number: 7270931Abstract: Antireflective compositions characterized by the presence of an Si-containing polymer having pendant chromophore moieties are useful antireflective coating/hardmask compositions in lithographic processes. These compositions provide outstanding optical, mechanical and etch selectivity properties while being applicable using spin-on application techniques. The compositions are especially useful in lithographic processes used to configure underlying material layers on a substrate, especially metal or semiconductor layers.Type: GrantFiled: October 6, 2003Date of Patent: September 18, 2007Assignee: International Business Machines CorporationInventors: Marie Angelopoulos, Wu-Song Huang, Arpan P. Mahorowila, Wayne Moreau, Dirk Pfeiffer, Ratnam Sooriyakumaran
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Patent number: 7270930Abstract: Heat-sensitive element comprising a) an optionally pretreated substrate; b) a positive working coating comprising (i) at least 40 wt.-%, based on the dry weight of the coating, of at least one polymer soluble in aqueous alkaline developer selected from novolak resins, functionalized novolak resins, polyvinylphenol resins, polyvinyl cresols and poly(meth)acrylates with phenolic and/or sulfonamide side groups, (ii) 01-20 wt.-%, based on the dry weight of the coating, of at least one (C4-C20 alkyl)phenol novolak resin insoluble in aqueous alkaline developer, and (iii) optionally at least one further component selected from polymer particles, surfactants, contrast dyes and pigments, inorganic fillers, antioxidants, print-out dyes, carboxylic acid derivatives of cellulose polymers, plasticizers and substances capable of absorbing radiation of a wavelength from the range of 650 to 1,300 nm and converting it into heat.Type: GrantFiled: August 9, 2004Date of Patent: September 18, 2007Assignee: Kodak Polychrome Graphics, GmbHInventors: Gerhard Hauck, Dietmar Frank
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Patent number: 7270936Abstract: A negative resist composition and a method for patterning semiconductor devices using the composition are provided. The negative resist composition contains an alkali-soluble hydroxy-substituted base polymer, a silicon-containing crosslinker having an epoxy ring, and a photoacid generator. In the method for patterning semiconductor devices, fine patterns are formed according to a bi-layer resist process using the negative resist composition.Type: GrantFiled: July 6, 2005Date of Patent: September 18, 2007Assignee: Samsung Electronics Co., Ltd.Inventor: Sang-Jun Choi
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Patent number: 7267925Abstract: A photosensitive composition containing: a sensitizing dye represented by the formula (1) as defined herein; an initiator compound capable of generating a radical, an acid, or a base; and a compound whose physical or chemical characteristic irreversibly changes by at least one of a radical, an acid, and a base.Type: GrantFiled: March 31, 2004Date of Patent: September 11, 2007Assignee: Fujifilm CorporationInventor: Akinori Shibuya
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Patent number: 7264914Abstract: This invention provides novel fluorine containing polymers which comprise at least one fluorinated olefin, at least one polycyclic ethylenically unsaturated monomer with a fused 4-membered carbocyclic ring and, optionally, other components. The polymers are useful for photoimaging compositions and, in particular, photoresist compositions (positive-working and/or negative-working) for imaging in the production of semiconductor devices. The polymers are especially useful in photoresist compositions having high UV transparency (particularly at short wavelengths, e.g., 157 nm) which are useful as base resins in resists and potentially in many other applications.Type: GrantFiled: August 8, 2003Date of Patent: September 4, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Frank L Schadt, III, Viacheslav Alexandrovich Petrov, Bruce Edmund Smart, William Brown Farnham
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Patent number: 7264918Abstract: A resist composition for liquid immersion lithography process, which comprises: (A) a polymer comprising (a1) alkali-soluble constitutional units each comprising an alicyclic group having both (i) a fluorine atom or a fluoroalkyl group and (ii) an alcoholic hydroxyl group, wherein the polymer changes in alkali-solubility due to the action of acid; and (B) an acid generator which generates acid due to exposure to light, and a method for forming a resist pattern using the resist composition. By the resist composition or the method, an adverse effect of the immersion liquid can be avoided while achieving high resolution and high depth of focus.Type: GrantFiled: March 24, 2004Date of Patent: September 4, 2007Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Kotaro Endo, Masaaki Yoshida, Taku Hirayama, Hiromitsu Tsuji, Toshiyuki Ogata, Mitsuru Sato