Binder Containing Patents (Class 430/905)
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Patent number: 7510816Abstract: A resist composition is provided comprising a polysiloxane, a specific acid generator, a nitrogen-containing organic compound, and a solvent. The resist composition exerts high-resolution performance without the problem of a T-top profile and is suited for the bilayer resist process using ArF exposure.Type: GrantFiled: October 4, 2005Date of Patent: March 31, 2009Assignee: Shin-Estu Chemical Co., Ltd.Inventors: Katsuya Takemura, Kazumi Noda, Youichi Ohsawa
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Patent number: 7507525Abstract: A lithographic printing plate precursor having a photosensitive layer containing (A) at least one saccharide selected from the group consisting of an oligosaccharide and a polysaccharide, (B) a binder polymer, (C) a compound having an addition polymerizable ethylenic unsaturated bond, and (D) a polymerization initiator, or a lithographic printing plate precursor having an undercoat layer comprising (A) at least one saccharide selected from the group consisting of an oligosaccharide and a polysaccharide, and a photosensitive layer containing (B) a binder polymer, (C) a compound having an addition polymerizable ethylenic unsaturated bond, and (D) a polymerization initiator.Type: GrantFiled: May 3, 2006Date of Patent: March 24, 2009Assignee: FUJIFILM CorporationInventor: Atsushi Sugasaki
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Patent number: 7507522Abstract: The present invention relates to novel unsaturated polycyclic compounds containing two fluoroalcohol substitutents. This invention also relates to homopolymers and copolymers derived from such unsaturated polycyclic compounds. The copolymers 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: May 17, 2005Date of Patent: March 24, 2009Assignee: E. I. DuPont de Nemours and CompanyInventors: Michael Karl Crawford, Hoang Vi Tran, Frank Leonard Schadt, III, Fredrick Claus Zumsteg, Jr., Andrew Edward Feiring, Michael Fryd
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Patent number: 7504195Abstract: A photosensitive polymer which can form a fine circuit pattern by exacting with extreme UV and deep UV, and can improve a line width stability of a pattern by significantly reducing line edge roughness after developing, and a photoresist composition including the same are disclosed. The photosensitive polymer for extreme UV and deep UV includes a repeating unit represented by the following Formula 1, in Formula 1, R1 and R1? are independently a hydrogen atom, methyl group, or trifluoromethyl group, and R2 is wherein Ra and Rb are independently alkyl group of 1 to 10 carbon atoms, aryl group of 6 to 10 carbon atoms, or arylalkyl group of 7 to 12 carbon atoms, and can be connected together to form ring, and a and b are mol % of each repeating unit with respect to the total repeating unit constituting the photosensitive polymer, and are 1 to 99 mol % and 1 to 99 mol % respectively.Type: GrantFiled: August 9, 2007Date of Patent: March 17, 2009Assignee: Dongjin Semichem Co., Ltd.Inventors: Deog-Bae Kim, Jae-Hyun Kim
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Patent number: 7504196Abstract: A positive resist composition that includes a base material component (A) that contains an acid-dissociable, dissolution-inhibiting group and exhibits increased alkali solubility under the action of acid, and an acid generator component (B) that generates acid upon exposure, wherein the base material component (A) contains a compound (A1), in which either a portion of, or all of, hydrogen atoms of phenolic hydroxyl groups within a polyhydric phenol compound, which has two or more phenolic hydroxyl groups, a molecular weight of 300 to 2,500, and is represented by a general formula (I) shown below, have been substituted with an acid-dissociable, dissolution-inhibiting group (II) represented by a general formula (II) shown below.Type: GrantFiled: February 9, 2006Date of Patent: March 17, 2009Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Daju Shiono, Taku Hirayama, Hideo Hada
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Patent number: 7501223Abstract: There is disclosed a polymer at least comprising repeating units represented by the following general formulae (1) and (2), and the polymer having a mass average molecular weight of 1,000 to 500,000. There can be provided a polymer, and a resist composition, in particular, a chemically amplified positive resist composition that exhibit higher resolution than conventional positive resist compositions, good in-plane dimension uniformity of developed resist patterns on substrates such as mask blanks and high etching resistance.Type: GrantFiled: September 25, 2007Date of Patent: March 10, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takanobu Takeda, Osamu Watanabe, Satoshi Watanabe, Ryuji Koitabashi, Keiichi Masunaga, Tamotsu Watanabe
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Patent number: 7501221Abstract: 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: March 10, 2009Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
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Patent number: 7501222Abstract: A polymer including a monomer represented by the following Formula and a photoresist composition including the same are disclosed. The polymer and photoresist composition can improve the resolution and the process margin due to the low activation energy of the deprotection reaction of the alcohol ester group including saturated cyclic hydrocarbyl group, and also can produce fine photoresist patterns because they have a stable PEB(Post Exposure Baking) temperature sensitivity, and further, can improve the focus depth margin and the line edge roughness of the resist layer. In the above Formula, R* is a hydrogen or methyl group, R1 is saturated hydrocarbyl group of 1 to 5 carbon atoms, R is mono-cyclic or multi-cyclic homo or hetero saturated hydrocarbyl group of 3 to 50 carbon atoms, and n is an integer of at least 2.Type: GrantFiled: June 21, 2006Date of Patent: March 10, 2009Assignee: Dongjin Semichem Co., Ltd.Inventors: Jung-Youl Lee, Jae-Woo Lee, Jae-Hyun Kim
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Patent number: 7498126Abstract: A photoacid generator has formula (1). A chemically amplified resist composition comprising the photoacid generator has advantages including a high resolution, focus latitude, long-term PED dimensional stability, and a satisfactory pattern profile shape. When the photoacid generator is combined with a resin having acid labile groups other than those of the acetal type, resolution and top loss are improved. The composition is suited for deep UV lithography.Type: GrantFiled: June 5, 2007Date of Patent: March 3, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Kazunori Maeda, Satoshi Watanabe
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Patent number: 7498116Abstract: A resist composition includes: (A) a resin that includes: a repeating unit represented by a following formula (I), and a repeating unit represented by a following formula (II); and (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation: wherein the variables in the formulae are defined in the specification.Type: GrantFiled: March 28, 2008Date of Patent: March 3, 2009Assignee: FUJIFILM CorporationInventors: Shuji Hirano, Shinichi Sugiyama
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Patent number: 7498123Abstract: Disclosed are novel aminium, diimonium, and polymethine borate dyes that have at least one absorption maximum in the infrared spectral region between about 700 and 2000 nm and that are useful as infrared absorbers, the anionic borate moiety having the formula: [BXaYb]?, in which a and b are integers with a ranging from 0 to 3 and b ranging from 1 to 4 and a+b=4; X, which may be identical or different, are each a halogen atom, an OH functional group, or a C1 to C20 alkyl or alicyclic radical, and Y, which may be identical or different, are each a phenyl radical, at least one Y substituted by at least one element or electron-withdrawing substituent such as a perfluoroalkyl group, or by one or more halogen atoms, or an aryl radical containing at least two aromatic ring members, which may also be further substituted. Such dyes may be incorporated into films or bulk materials to form light filters for electromagnetic radiation, including laser radiation.Type: GrantFiled: March 3, 2005Date of Patent: March 3, 2009Assignee: Exciton, Inc.Inventor: Paul A. Cahill
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Patent number: 7494760Abstract: A photoacid generator has formula (1) wherein R is H, F, Cl, nitro, alkyl or alkoxy, n is 0 or 1, m is 1 or 2, r is an integer of 0-4, and r? is an integer of 0-5. A chemically amplified resist composition comprising the photoacid generator has advantages including a high resolution, focus latitude, long-term PED dimensional stability, and a satisfactory pattern profile shape. When the photoacid generator is combined with a resin having acid labile groups other than those of the acetal type, resolution and top loss are improved. The composition is suited for deep UV lithography.Type: GrantFiled: June 1, 2007Date of Patent: February 24, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Katsuya Takemura, Akihiro Seki
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Patent number: 7494763Abstract: The present invention provides a polyhydric phenol compound represented by the formula (I): wherein at least one selected from R1, R2, R3, R4, and R5 is a group represented by the formula (II): wherein X1, X2, X3 and X4 each independently represent a hydrogen atom or a C1-C4 alkyl group, n represents an integer of 0 to 3, Z1 represents a C1-C6 alkyl group or a C3-C12 cycloalkyl group, and ring Y represents an alicyclic hydrocarbon group, and the others are hydrogen atoms, and a chemically amplified resist composition containing the same.Type: GrantFiled: October 22, 2007Date of Patent: February 24, 2009Assignee: Sumitomo Chemical Company, LimitedInventors: Ichiki Takemoto, Nobuo Ando, Junji Shigematsu
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Patent number: 7491483Abstract: A polymer is composed of recurring units of hydroxyvinylnaphthalene, (meth)acrylic units having a lactone ring fused to a bridged ring, and (meth)acrylic units having acid labile groups. A positive resist composition comprising the polymer as a base resin, when exposed to high-energy radiation and developed, exhibits a high sensitivity, a high resolution, and a minimal line edge roughness due to controlled swell during development.Type: GrantFiled: March 5, 2007Date of Patent: February 17, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Takeshi Kinsho, Takanobu Takeda
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Patent number: 7491485Abstract: This resist composition according to the present invention includes 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 an acid upon exposure, wherein the acid generator component (B) includes an acid generator (B1) represented by a general formula (b1-6-1) shown below and an acid generator (B2) represented by a general formula (b1-6-2) shown below: (wherein, R40 represents a hydrogen atom or an alkyl group; R41 represents a halogen atom, a halogenated alkyl group, an alkyl group, an acetyl group, a carboxyl group or a hydroxyalkyl group; R42 and R43 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an acetyl group, an alkoxy group, a carboxyl group or a hydroxyalkyl group; n0 to n3 each independently represents an integer of 0 to 3, with the proviso that n0+n1 is 5 or less; R13 each independently represents a linear or branched alkyl group of 1 to 10 carbonType: GrantFiled: May 20, 2008Date of Patent: February 17, 2009Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Masaru Takeshita, Komei Hirahara
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Patent number: 7488568Abstract: A resist composition including a base component (A) and an acid-generator component (B), the acid-generator component (B) including an acid generator (B1) including a compound represented by general formula (b1-8) shown below (wherein R401 represents an acid dissociable, dissolution inhibiting group; R41 to R43 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an acetyl group, an alkoxy group, a carboxy group or a hydroxyalkyl group; Q represents a divalent linking group or a single bond; and X? represents an anion) or an acid generator (B1?) including a compound represented by general formula (b1-9) shown below (wherein R402 and R403 each independently represents a hydrogen atom, an alkyl group or a halogenated alkyl group; R404 represents an alkyl group or a halogenated alkyl group, wherein R403 and R404 may be bonded to each other to form a ring structure; and X? represents an anion).Type: GrantFiled: April 1, 2008Date of Patent: February 10, 2009Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takeshi Iwai, Hideo Hada, Masaru Takeshita, Akiya Kawaue, Keita Ishiduka, Hiroaki Shimizu, Kyoko Ohshita, Tsuyoshi Nakamura, Komei Hirahara, Yuichi Suzuki, Takehiro Seshimo, Kensuke Matsuzawa
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Patent number: 7488567Abstract: A polymer comprising recurring units of formula (1) wherein R1 is F or fluoroalkyl, R2 is alkylene or fluoroalkylene, and R3 is an acid labile group and having a Mw of 1,000-500,000 is used to formulate a resist composition, which is processed by the lithography involving ArF exposure and offers many advantages including resolution, minimal line edge roughness, etch resistance, and minimal surface roughness after etching. The composition performs well when processed by the ArF immersion lithography with liquid interposed between the projection lens and the wafer.Type: GrantFiled: May 25, 2006Date of Patent: February 10, 2009Assignees: Panasonic Corporation, Central Glass Co., Ltd., Shin-Etsu Chemical Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Kazuhiko Maeda, Haruhiko Komoriya, Michitaka Ootani
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Patent number: 7485408Abstract: Fluorine-containing silicon compounds having the general formula (1): wherein X1, X2, and X3 each are hydrogen, hydroxyl, halogen, a straight, branched or cyclic alkoxy group of 1 to 6 carbon atoms, or a monovalent organic group of 1 to 20 carbon atoms having a straight, branched, cyclic or polycyclic skeleton, Y is a divalent organic group, R1 and R2 are each independently hydrogen or a monovalent organic group of 1 to 20 carbon atoms having a straight, branched, cyclic or polycyclic skeleton, or R1 and R2 may bond together to form a ring with the carbon atom to which they are attached silicone resins obtained from the compounds of formula (1) has an appropriate acidity to enable formation of a finer pattern while minimizing the pattern collapse by swelling when used in a resist composition.Type: GrantFiled: March 5, 2007Date of Patent: February 3, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeshi Kinsho, Mutsuo Nakashima, Koji Hasegawa, Takeru Watanabe
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Patent number: 7485406Abstract: The invention provides a photostorage solid drawing medium comprising a solvent, a resin soluble in the solvent, a photostorage pigment and a gelling agent, wherein the photostorage pigment comprises a long afterglow fluorescent substance comprising an alkaline earth aluminosilicate as a matrix activated with a rare earth element wherein the alkaline earth element is at least one selected from the group consisting of strontium, calcium, magnesium and barium. The solvent used is a polar solvent, particularly a mixture of water and a water-soluble organic solvent, or at least one alcoholic solvent selected from the group consisting of glycols, glycol ethers, glycol ether esters and monovalent alcohols.Type: GrantFiled: April 7, 2006Date of Patent: February 3, 2009Assignee: Sakura Color Products CorporationInventors: Hidetoshi Fukuo, Masamitsu Takahashi, Kotaro Sumitomo
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Patent number: 7485413Abstract: 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: February 3, 2009Assignee: Kabushiki Kaisha ToshibaInventor: Satoshi Saito
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Patent number: 7485409Abstract: The present invention provides a planographic printing plate precursor including a support and a positive recording layer formed on the support and containing: (A) a polymer having a structural unit represented by the following general formula (1), (B) a photo-thermal converting agent, and (C) an amino compound having a methylol group or an alkoxymethyl group; and a positive recording layer whose solubility in an alkaline developer is improved by exposure to light or by heating. In general formula (1), R1 represents an alkyl group or a cyclic group, x represents 0 or 1, and A represents a bivalent bonding group. According to the invention, a positive planographic printing plate precursor for use with infrared lasers having excellent chemical resistance and wide image development latitude can be obtained.Type: GrantFiled: September 22, 2005Date of Patent: February 3, 2009Assignee: FujiFilm CorporationInventor: Akira Nagashima
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Patent number: 7482108Abstract: The invention provides a polymer compound capable of forming a positive resist composition that can form a high-resolution pattern with a reduced level of LER, an acid generator formed from such a polymer compound, a positive resist composition that includes such a polymer compound, and a method for forming a resist pattern that uses such a positive resist composition.Type: GrantFiled: July 1, 2005Date of Patent: January 27, 2009Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Shogo Matsumaru, Masaru Takeshita, Takeshi Iwai, Hideo Hada
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Patent number: 7476489Abstract: The invention relates to low-temperature curable photosensitive compositions containing a polyamic acid, which compositions are developable in aqueous alkaline solutions and are curable, at a temperature of at least 160° C. and up to 200° C., to low modulus polyimides suitable for use in electronic circuitry applications, and which are particularly suitable for use in flexible circuit applications where low curl, low temperature curing, and good adhesion is a significant advantage.Type: GrantFiled: November 10, 2005Date of Patent: January 13, 2009Assignee: E.I. DuPont de NemoursInventors: Thomas E. Dueber, Michael W. J. West, Kuppusamy Kanakarajan, Brian C. Auman
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Patent number: 7476488Abstract: 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 24, 2007Date of Patent: January 13, 2009Assignee: Kabushiki Kaisha ToshibaInventor: Satoshi Saito
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Patent number: 7462438Abstract: A resist film made of a resist material including 4-pentanelactam, that is, hetero cyclic ketone, is formed on a substrate, and subsequently, pattern exposure is performed by irradiating the resist film with exposing light through a mask. Then, the resist film having been subjected to the pattern exposure is developed, thereby forming a resist pattern.Type: GrantFiled: May 2, 2006Date of Patent: December 9, 2008Assignee: Panasonic CorporationInventors: Masayuki Endo, Masaru Sasago
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Patent number: 7459261Abstract: There is disclosed a resist composition which comprises, at least, a polymer in which a sulfonium salt having a polymerizable unsaturated bond, a (meth)acrylate having a lactone or a hydroxyl group as an adhesion group, and a (meth)acrylate having an ester substituted with an acid labile group are copolymerized. There can be provided a resist composition with high resolution which has high sensitivity and high resolution to high energy beam, especially to ArF excimer laser, F2 excimer laser, EUV, X-ray, EB, etc., has reduced line edge roughness, and comprises a polymeric acid generator which has insolubility in water, and sufficient thermal stability and preservation stability.Type: GrantFiled: December 19, 2005Date of Patent: December 2, 2008Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Youichi Ohsawa, Seiichiro Tachibana
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Patent number: 7449276Abstract: The invention provides a positive photoresist composition which exhibits a high level of etching resistance and attains high resolution, and enables the formation of a fine pattern using an electron beam exposure step, as well as a method for forming a resist pattern that uses the positive photoresist composition. This positive photoresist composition for use with EB contains a resin component (A) that exhibits increased alkali solubility under the action of acid, an acid generator component (B) that generates acid on exposure, and an organic solvent (C), wherein the component (A) comprises a copolymer containing a first structural unit (a1) derived from hydroxystyrene and a second structural unit (a2) derived from a (meth)acrylate ester having an alcoholic hydroxyl group, and a portion of the hydroxyl groups of the structural units (a1) and the alcoholic hydroxyl groups of the structural units (a2) are protected with acid dissociable, dissolution inhibiting groups.Type: GrantFiled: April 22, 2004Date of Patent: November 11, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takuma Hojo, Kiyoshi Ishikawa, Tsuyoshi Nakamura, Tasuku Matsumiya
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Patent number: 7449281Abstract: A photosensitive resin composition for a black matrix comprises (A) an alkali-soluble resin; (B) a photopolymerizable monomer; (C) a photoinitiator; (D) a solvent; and (E) a black pigment; wherein the alkali-soluble resin (A) comprises a functional group having a general formula (a-1); viscosity of said photosensitive resin composition for the black matrix is 0.5-4.0 cps at 25° C.; the solid content of said photosensitive resin composition is 5-17.5 wt. %; and said solvent (D) has a saturated vapor pressure below 4.5 mmHg at 20° C.; which presents no pinhole on the surface after low pressure drying, no line and cloud defect on the film, good inner uniformity of the coated film and high photosensitivity after pre-bake, high heat resistance for black matrix after post-bake, especially no poor coating on substrates of LCD by the slit coating. (Each of R is independently H, linear or branch alkyl of C1-C5, phenyl or halogen.Type: GrantFiled: January 18, 2007Date of Patent: November 11, 2008Assignee: Chi-Mei CorporationInventor: Chun-Hsien Lee
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Patent number: 7442490Abstract: A positive resist composition comprising: a resin which increases solubility in an alkali developing solution by an action of an acid and comprises a repeating unit containing a lactone structure and a cyano group and a repeating unit containing a first acid-decomposable group; a resin which increases solubility in an alkali developing solution by an action of an acid and comprises a repeating unit containing a lactone structure and a cyano group and a repeating unit containing a second acid-decomposable group which is different from the first acid-decomposable group; a compound which generates an acid upon irradiation of an actinic ray or a radiation; and a solvent.Type: GrantFiled: March 16, 2007Date of Patent: October 28, 2008Assignee: FUJIFILM CorporationInventors: Kaoru Iwato, Kunihiko Kodama
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Patent number: 7442488Abstract: There is provided a positive type photosensitive paste composition for a plasma display panel (PDP) electrode, including a conductive powder, an inorganic binder, and a photosensitive vehicle. The photosensitive vehicle includes an organic binder represented by formula (1), a photoacid generator, a solvent, and other additives: where R1 is H or CH3; R2 is a saturated or unsaturated C1-C6 alkyl group or a C1-C6 group containing an ether group, a carbonyl group or an ester group; R3 is a group having a hydroxyl group; R4 is hydrogen or a group having a carboxylic group; and R5 is a protecting group. Further embodiments provide a film prepared with such a paste; as well as a PDP electrode prepared with such a paste and a PDP having one or more such electrodes.Type: GrantFiled: September 29, 2005Date of Patent: October 28, 2008Inventors: Beom-Wook Lee, Dong-Hee Han, Sang-Wook Sin, Jin-Hwan Jeon
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Patent number: 7435530Abstract: 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: January 9, 2007Date of Patent: October 14, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
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Patent number: 7435529Abstract: A photosensitive composition comprising: a sensitizing dye represented by the formula (I) defined herein, in which Z represents a substituted divalent linking group forming a 5-membered or 6-membered ring, provided that a total volume of substituents arranged on the 5-membered or 6-membered ring formed by Z is 200 ?3 or more; R1 represents a hydrogen atom or a monovalent non-metal atomic group; A represents a substituted or unsubstituted aromatic ring or hetero ring; and R1 and A may be taken together to form an aliphatic or aromatic ring; an activator compound being capable of causing a chemical change due to a mutual action with an electron excited state to be generated by light absorption of the sensitizing dye, thereby generating a radical or an acid; and a polymerizable compound being capable of reacting with at least one of a radical and an acid.Type: GrantFiled: July 1, 2005Date of Patent: October 14, 2008Assignee: FUJIFILM CorporationInventors: Yohei Ishiji, Akinori Shibuya
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Patent number: 7432034Abstract: A negative resist composition of the present invention comprises: (A) an alkali-soluble resin; (B-1) a cross-linking agent capable of cross-linking with the alkali-soluble resin (A) by the action of an acid, in which the cross-linking agent is a phenol compound containing: in the molecule one or more benzene rings; and at least two cross-linking groups bonded to any of the benzene rings, the cross-linking group being a group selected from the group consisting of a hydroxymethyl group, an alkoxymethyl group and an acyloxymethyl group; (B-2) a cross-linking agent capable of cross-linking with the alkali-soluble resin (A) by the action of an acid, in which the cross-linking agent contains at least two specific groups; and (C) a compound capable of generating an acid upon irradiation with an actinic ray or radiation.Type: GrantFiled: August 18, 2003Date of Patent: October 7, 2008Assignee: FUJIFILM CorporationInventors: Shoichiro Yasunami, Koji Shirakawa
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Patent number: 7419759Abstract: The photoresist composition of the present invention includes a solvent mixture, a resin, a photo acid generator, and a quencher, the solvent mixture comprising a first solvent containing an ether compound and a second solvent having a polarity stronger than the first solvent, wherein an amount of the first solvent is in a range of about 61% to about 79% by weight, and an amount of the second solvent is in a range of about 21% to about 39% by weight based on a total weight of the solvent mixture.Type: GrantFiled: May 27, 2005Date of Patent: September 2, 2008Assignee: Samsung Electronics Co., Ltd.Inventors: Kyoung-Mi Kim, Jae-Ho Kim, Yeu-Young Youn, Youn-Kyung Wang
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Patent number: 7416832Abstract: A positive resist composition capable of forming a resist pattern having excellent shape is provided. This composition is a positive resist composition including a base resin component (A) and an acid generator component (B) generating an acid under exposure, which are dissolved in an organic solvent, wherein the base resin component (A) is a silicone resin, and the organic solvent contains propylene glycol monomethyl ether (x1) and a solvent (S2) having a boiling point higher than that of the propylene glycol monomethyl ether.Type: GrantFiled: March 28, 2005Date of Patent: August 26, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Daisuke Kawana, Tomotaka Yamada, Takayuki Hosono, Koki Tamura
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Patent number: 7413843Abstract: A base polymer of a resist material includes a unit represented by a general formula of the following Chemical Formula 3: wherein R1, R2 and R3 are the same or different and are a hydrogen atom, a fluorine atom, a straight-chain alkyl group, a branched or cyclic alkyl group or a fluoridated alkyl group with a carbon number not less than 1 and not more than 20; R4 is a straight-chain alkylene group or a branched or cyclic alkylene group with a carbon number not less than 0 and not more than 20; and R5 and R6 are the same or different and are a hydrogen atom, a straight-chain alkyl group, a branched or cyclic alkyl group, a fluoridated alkyl group with a carbon number not less than 1 and not more than 20, or a protecting group released by an acid.Type: GrantFiled: December 20, 2006Date of Patent: August 19, 2008Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Hirokazu Imori, Toshiaki Fukuhara
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Patent number: 7405028Abstract: A bottom antireflective coating for photolithography at 157 nm or less, where the bottom antireflective coating includes a crosslinkable polymer which contains cinnamic acid derivatives.Type: GrantFiled: January 28, 2005Date of Patent: July 29, 2008Assignee: Infineon Technologies, AGInventor: Christoph Hohle
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Patent number: 7402372Abstract: A positive resist composition includes a resin (A) that increases alkali solubility due to action of an acid, wherein the resin comprises a copolymer containing a first structural unit (a1) derived from hydroxystyrene, and a second structural unit (a2) derived from a (meth)acrylate with an alcoholic hydroxyl group, and a weight average molecular weight of the copolymer is within a range from 2000 to 8500, and 10 mol % to 25 mol % of a combined total of hydroxyl groups within the structural units (a1) and alcoholic hydroxyl groups within the structural units (a2) are protected with acid dissociable, dissolution inhibiting groups, an acid generator (B) that generates an acid on exposure to light, and polypropylene glycol (C).Type: GrantFiled: June 10, 2004Date of Patent: July 22, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Mitsuo Hagihara, Taku Nakao, Kazuyuki Nitta
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Patent number: 7402376Abstract: A photosensitive resin composition which gives a dry film having a sand blast proof property and a development property in a well-balanced manner. A photosensitive resin composition containing a carboxy group-containing urethane (meth)acrylate compound having two or more of (meth)acryloyl groups per molecule whose acid value of less than 10 mg KOH/g, an alkali soluble polymer compound, a photopolymerization initiator and a photopolymerizable compound (D) including in the structure thereof a structural unit represented by the formula (I) gives such a well-balanced properties.Type: GrantFiled: April 5, 2005Date of Patent: July 22, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Syunji Nakazato, Ryuma Mizusawa, Hiroyuki Obiya, Takashi Ono, Yusuke Fujito
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Patent number: 7402379Abstract: A resist exposure system and a method of forming a pattern on a resist are provided and include an exposure source, a photoresist composition, and a mask positioned therebetween. The resist composition comprises a first photoresist X and a second photoresist Y. The first photoresist X absorbs at a higher wavelength than the second photoresist Y. The second photoresist Y has a lower glass transitional temperature than the first photoresist X.Type: GrantFiled: February 23, 2006Date of Patent: July 22, 2008Assignee: Micron Technology, Inc.Inventor: Yoshiki Hishiro
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Patent number: 7399573Abstract: The negative resist compositions especially suitable for electron beam-based lithographic processes are obtained by using a polymeric component containing first silsesquioxane moieties functionalized with a first reactive group having a first crosslinking reactivity and a first dissolution rate in aqueous alkaline solutions, and second silsesquioxane moieties functionalized with a second reactive group having a second crosslinking reactivity and a second dissolution rate in aqueous alkaline solutions, said reactivities being different from one another and said dissolution rates being different from one another. These negative resists enable improved negative lithographic processes, especially in the context of mask-making and direct-write techniques using electron beam lithography. The negative resists are also useful more generally in methods of forming patterned material features and advantageously show reduced incidence of image collapse at smaller groundrules.Type: GrantFiled: October 25, 2006Date of Patent: July 15, 2008Assignee: International Business Machines CorporationInventors: Wu-Song S. Huang, Lidija Sekaric, James J. Bucchignano, David P. Klaus, Raman Viswanathan
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Patent number: 7396634Abstract: A photosensitive composition comprising: a sensitizing dye represented by the following formula (1): in which A represents an optionally substituted aromatic ring or an optionally substituted hetero ring; X represents an oxygen atoms a sulfur atom, or —N(R6)—; and R1, R2, R3, R4, R5, and R6 each independently represents a hydrogen atom or a monovalent non-metal atomic group; an activator compound being capable of causing a chemical change due to a mutual action with light absorption of the sensitizing dye represented by the formula (1) so as to generate at least one of a radical, an acid and a base; and a compound being capable of reacting with at least one of a radical and an acid so that physical or chemical characteristics thereof change irreversibly.Type: GrantFiled: July 29, 2005Date of Patent: July 8, 2008Assignee: FUJIFILM CorporationInventor: Akinori Shibuya
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Patent number: 7390612Abstract: 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: June 24, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
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Patent number: 7390608Abstract: In a first aspect, silicon polymers are provided that have controlled ratio of silanol (Si—OH) moieties:Si atoms and/or a controlled amount of alkaline aqueous-solubilizing groups. Si-polymers of the invention are particularly useful as a photoresist resin component. In a further aspect, halogenated sulfonamide and thiol compounds and Si-containing polymers comprising such reacted monomers are provided.Type: GrantFiled: October 21, 2003Date of Patent: June 24, 2008Assignee: Rohm and Haas Electronic Materials LLCInventors: George G. Barclay, Subbareddy Kanagasabapathy
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Patent number: 7390609Abstract: New polymers are provided that have non-carbon tetravalent species (Si, Ti, Ge, Zr, Sn) and photoimageable compositions that contain such polymers. Preferred polymers are organic, e.g. one or more polymer repeat units comprise carbon atom(s). Particularly preferred are polymers that comprise SiO2 or TiO2 repeat units and which can be highly useful as a resin component of resists imaged at short wavelengths such as sub-300 nm and sub-200 nm.Type: GrantFiled: March 3, 2004Date of Patent: June 24, 2008Assignee: Rohm and Haas Electronic Materials LLCInventors: Anthony Zampini, Tao Zhang, Jaihyoung Lee
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Patent number: 7378218Abstract: A fluorinated polymer comprising recurring units of formulae (1a) to (1d) and having a Mw of 1,000-500,000 is provided. R1 is an acid labile group, R2 is a single bond or methylene, a1, a2, a3, and a4 are numbers from more than 0 to less than 1, and 0<a1+a2+a3+a4?1, b is 1 or 2, and c is 0 or 1.Type: GrantFiled: February 2, 2006Date of Patent: May 27, 2008Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Kazuhiko Maeda, Haruhiko Komoriya, Michitaka Ootani
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Patent number: 7374860Abstract: The invention provides a positive resist composition for the pattern formation by the use of actinic rays or radiation, ensuring that the sensitivity, resolution and pattern profile are good, the line edge roughness is small and the surface roughness is satisfied, and a pattern forming method using the composition, wherein the positive resist composition is a positive resist composition comprising (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation, and (B) a resin of which solubility in an alkali developer increases under the action of an acid, the resin comprising a specific repeating unit; and a pattern forming method using the composition.Type: GrantFiled: March 20, 2006Date of Patent: May 20, 2008Assignee: Fuji Film CorporationInventors: Shuji Hirano, Kazuyoshi Mizutani
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Patent number: 7371505Abstract: A positive working photosensitive composition which is useful in the manufacturing step of a semiconductor such as IC, the manufacture of a circuit board such as liquid crystals and thermal heads, and other fabrication steps and has an excellent resolution and line edge roughness, and a method for forming a pattern using the same, are provided, which are a photosensitive composition containing (A) a resin having a repeating unit having a specific group, whose solubility in an alkaline developer increases by the action of an acid, and a method for forming a pattern using the same.Type: GrantFiled: June 28, 2005Date of Patent: May 13, 2008Assignee: FUJIFILM CorporationInventor: Kunihiko Kodama
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Patent number: 7371503Abstract: A sulfonium salt compound excelling in transparency to deep ultraviolet rays at a wavelength of 220 nm or less, exhibiting well-balanced excellent performance such as sensitivity, resolution, pattern form, LER, and storage stability when used as a photoacid generator, a photoacid generator comprising the sulfonium salt compound, and a positive-tone radiation-sensitive resin composition containing the photoacid generator. The sulfonium salt compound is shown by the following formula (I), wherein R1 represents a halogen atom, an alkyl group, a monovalent alicyclic hydrocarbon group, an alkoxyl group, or —OR3 group, wherein R3 is a monovalent alicyclic hydrocarbon group, R2 represents a (substituted)-alkyl group or two or more R2 groups form a cyclic structure, p is 0-7, q is 0-6, n is 0-3, and X? indicates a sulfonic acid anion. The positive-tone radiation-sensitive resin composition comprises (A) a photoacid generator of the sulfonium-salt compound and (B) an acid-dissociable group-containing resin.Type: GrantFiled: January 9, 2004Date of Patent: May 13, 2008Assignee: JSR CorporationInventors: Takashi Miyamatsu, Hirokazu Niwata, Satoshi Ebata, Yong Wang
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Patent number: 7364831Abstract: A positive resist composition includes a resin component (A) whose alkaline solubility changes by an action of an acid, an acid generator component (B), and polypropylene glycol, wherein the component (A) includes a resin component (A1) including a constitutional unit (a1) represented by general formula (I), a constitutional unit (a2) represented by general formula (II), and a constitutional unit (a3) having an acid dissociable dissolution inhibiting group, wherein R represents a hydrogen atom or a methyl group, and m represents an integer of 1 to 3, wherein R represents a hydrogen atom or a methyl group, and R1 represents alkyl group having a carbon number of 1 to 5, and l represents an integer of 0 to 3.Type: GrantFiled: May 6, 2005Date of Patent: April 29, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Kouji Yonemura, Taku Nakao