Cationic Or Anionic Patents (Class 430/914)
  • Patent number: 7579131
    Abstract: A positive resist composition comprising: (A) a fluorine atom-containing resin; (B) a compound generating an acid upon irradiation with an actinic ray; and (C) a non-polymer dissolution inhibitor having a specific structure.
    Type: Grant
    Filed: July 23, 2004
    Date of Patent: August 25, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Tomoya Sasaki
  • Patent number: 7569324
    Abstract: Sulfonate salts have the formula: R1COOCH2CH2CF2CF2SO3?M+ wherein R1 is alkyl, aryl or hetero-aryl, M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oxime sulfonates and sulfonyloxyimides derived from these salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: June 25, 2007
    Date of Patent: August 4, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
  • Patent number: 7556909
    Abstract: Sulfonate salts have the formula: CF3—CH(OH)—CF2SO3?M+ wherein M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Because of inclusion within the molecule of a hydroxyl group which is a polar group, the sulfonic acids are effective for restraining the length of acid diffusion through hydrogen bond or the like. The photoacid generators that generate these sulfonic acids perform well during the device fabrication process including coating, pre-baking, exposure, post-exposure baking, and developing steps. The photoacid generators are little affected by water left on the wafer during the ArF immersion lithography.
    Type: Grant
    Filed: October 27, 2006
    Date of Patent: July 7, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe, Masaki Ohashi
  • Patent number: 7556908
    Abstract: The present invention provides a chemically amplified positive resist composition comprising (A) a resin which comprises (i) a structural unit of the formula (I) and (ii) at least one structural unit selected from the group consisting of structural units of the formulas (II), (O/II), (IV) and (V) and (B) an acid generator. The present invention further provides a novel monomers useful for the resist composition, and process for the monomers and the compositions.
    Type: Grant
    Filed: April 21, 2005
    Date of Patent: July 7, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ichiki Takemoto, Isao Yoshida, Takayuki Miyagawa
  • Patent number: 7550545
    Abstract: To provide a fluoropolymer having functional groups and having high transparency in a wide wavelength region, and a resist composition comprising the fluoropolymer. A fluoropolymer (A) having monomer units formed by polymerization of a fluorinated diene represented by the following formula (1): CF2?CFCH2CH-Q-CH2CH?CH2??(1) wherein Q is (CH2)aC(CF3)2OR4 (wherein a is an integer of from 0 to 3, R4 is an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms which may have an etheric oxygen atom, an alkoxycarbonyl group having at most 6 carbon atoms, or CH2R5 (wherein R5 is an alkoxycarbonyl group having at most 6 carbon atoms)), or (CH2)dCOOR6 (wherein d is 0 or 1, and R6 is a hydrogen atom, or an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms), a process for its production and a resist composition having the fluoropolymer (A) as a base.
    Type: Grant
    Filed: May 9, 2007
    Date of Patent: June 23, 2009
    Assignee: Asahi Glass Company, Limited
    Inventors: Yoko Takebe, Isamu Kaneko
  • Patent number: 7547501
    Abstract: The present application relates to photoactive materials having the formula wherein C1+ is a cation; each of R30, R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, and R41 are selected from hydrogen, alkyl, alkyl chain optionally containing one or more O atoms, halide, aryl, aralkyl, alkoxyalkyl, cycloalkyl, hydroxyl, and alkoxy, the alkyl, alkyl chain optionally containing one or more O atoms, aryl, aralkyl, alkoxyalkyl, cycloalkyl, and alkoxy groups being unsubstituted or substituted.
    Type: Grant
    Filed: October 5, 2006
    Date of Patent: June 16, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Ralph R. Dammel, M. Dalil Rahman, David L. Rentkiewicz, Karl van Werden
  • Patent number: 7534550
    Abstract: A positive resist composition includes a resin component (A) and an acid generator component (B), wherein the component (A) is a copolymer that includes a structural unit (a1) derived from an (?-lower alkyl)acrylate ester that contains a monocyclic or polycyclic group-containing acid dissociable, dissolution inhibiting group, a structural unit (a2) derived from an (?-lower alkyl)acrylate ester that contains a lactone ring, a structural unit (a3) derived from an (?-lower alkyl)acrylate ester that contains a polar group-containing polycyclic group, and a structural unit (a4).
    Type: Grant
    Filed: April 7, 2005
    Date of Patent: May 19, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Takeshi Iwai
  • Patent number: 7524610
    Abstract: An oxetane-containing compound, a photoresist composition including the same, a method of preparing patterns using the photoresist composition, and an inkjet print head including polymerization products of the oxetane-containing compound.
    Type: Grant
    Filed: June 26, 2007
    Date of Patent: April 28, 2009
    Assignee: Samsung Electronics Co., Ltd
    Inventors: Kyu-sik Kim, Jin-baek Kim, Young-ung Ha, Byung-ha Park, Ji-young Park, Su-min Kim
  • Patent number: 7524614
    Abstract: A radiation-sensitive composition includes a radically polymerizable component and an iodonium borate initiator composition capable of generating radicals sufficient to initiate polymerization of the free radically polymerizable component upon exposure to imaging radiation. The iodonium borate composition includes a particular diaryliodonium borate compound having organic substituents to provide a sum of at least 6 carbon atoms on the iodonium cation phenyl rings. This composition can be applied to a suitable substrate to provide a negative-working imageable element with improved digital speed and good shelf life and that can be imaged to provide lithographic printing plates. The imaged elements can be developed either on-press or off-press using alkaline developers.
    Type: Grant
    Filed: May 26, 2006
    Date of Patent: April 28, 2009
    Assignee: Eastman Kodak Company
    Inventors: Ting Tao, Scott A. Beckley
  • Patent number: 7514203
    Abstract: Disclosed is a positive photoresist composition used for a liquid crystal display. The positive photoresist composition of the present invention includes 3 to 50% by weight of binder resin having a certain structure, 2 to 40% by weight of a photoactive compound and 10 to 94% by weight of an organic solvent. The positive photoresist composition according to the present invention may be useful to form a pattern for an organic insulator of a liquid crystal display, metal patterning, a bump, hole drilling and UV overcoat since it has good basic physical properties such as UV transmittance, film retention, pattern stability, chemical resistance and so on, as well as an excellent heat resistance.
    Type: Grant
    Filed: December 21, 2005
    Date of Patent: April 7, 2009
    Assignee: Samyangems Co., Ltd.
    Inventors: Bong-Seok Moon, Hyo-Jeong Kim, Jin-Gon Kim, Yang-Hyun Yoo, Min-Ji Kim, Mi-Kyeong Jeong, Kwon-Yil Yoo, Nak-Chil Jung, Seon-Ho Kim
  • Patent number: 7510816
    Abstract: 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: Grant
    Filed: October 4, 2005
    Date of Patent: March 31, 2009
    Assignee: Shin-Estu Chemical Co., Ltd.
    Inventors: Katsuya Takemura, Kazumi Noda, Youichi Ohsawa
  • Patent number: 7501222
    Abstract: 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: Grant
    Filed: June 21, 2006
    Date of Patent: March 10, 2009
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jung-Youl Lee, Jae-Woo Lee, Jae-Hyun Kim
  • Patent number: 7498393
    Abstract: A fluoropolymer having functional groups and having high transparency in a wide wavelength range is provided, and a resist composition and a composition for a resist protective film, comprising the fluoropolymer, wherein the fluoropolymer has monomer units formed by cyclopolymerization of a fluorinated diene represented by the formula (1): CF2?CFCF2C(CF3)(OR1)—(CH2)nCR2?CHR3??(1) wherein R1 is a hydrogen atom, an alkyl group having at most 20 carbon atoms, or (CH2)aCOOR4 (wherein a is 0 or 1, and R4 is a hydrogen atom or an alkyl group having at most 20 carbon atoms), each of R2 and R3, which are independent of each other, is a hydrogen atom or an alkyl group having at most 12 carbon atoms, and n is 0 or 2, provided that when n is 0, at least one of R1, R2 and R3 is other than a hydrogen atom.
    Type: Grant
    Filed: January 25, 2007
    Date of Patent: March 3, 2009
    Assignee: Asahi Glass Company, Limited
    Inventors: Yoko Takebe, Masataka Eda, Osamu Yokokoji, Takashi Sasaki
  • Patent number: 7485407
    Abstract: Disclosed are a siloxane compound, a photoresist composition using the same, and a method of forming a pattern, wherein the siloxane compound is having a general formula: wherein R1 is a tertiary butyl group or a 1-(tert-butoxy)ethyl group, and R2 and R3 is each independently a lower alkyl group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: December 18, 2006
    Date of Patent: February 3, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim, Do-Young Kim
  • Patent number: 7482107
    Abstract: Photoresist compositions having a resin binder with an acid labile blocking group with an activation energy in excess of 20 Kcal/mol. for deblocking, a photoacid generator capable of generating a halogenated sulfonic acid upon photolysis and optionally, a base.
    Type: Grant
    Filed: March 23, 2006
    Date of Patent: January 27, 2009
    Assignee: Shipley Company, L.L.C.
    Inventors: James W. Thackeray, James F. Cameron, Roger F. Sinta
  • Patent number: 7468235
    Abstract: Provided are a barrier coating composition and a method of forming photoresist pattern by an immersion photolithography process using the same. The barrier coating composition includes a polymer corresponding to formula I having a weight average molecular weight (Mw) of 5,000 to 100,000 daltons and an organic solvent, wherein the expressions 1+m+n=1; 0.1?1/(1+m+n)?0.7; 0.3?m/(1+m+n)?0.9; and 0.0?n/(1+m+n)?0.6 are satisfied; Rf is a C1 to C5 fluorine-substituted hydrocarbon group; and Z, if present, includes at least one hydrophilic group. Compositions according to the invention may be used to form barrier layers on photoresist layers to suppress dissolution of photoresist components during immersion photolithography while allowing the barrier layer to be removed by alkaline developing solutions.
    Type: Grant
    Filed: June 7, 2006
    Date of Patent: December 23, 2008
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Mitsuhiro Hata, Sang-Jun Choi, Man-Hyoung Ryoo
  • Patent number: 7465527
    Abstract: The resist material contains a photo-acid generator having an absorption peak to exposure light having a wavelength of less than 300 nm, and a second photo-acid generator having an absorption peak to exposure light having a wavelength of 300 nm or more. The method for forming a resist pattern comprises a step for selectively exposing which exposes a coating film of the resist material to an exposure light having a wavelength of less than 300 nm, and a step for selectively exposing by using an exposure light having a wavelength of 300 nm or more. The semiconductor device comprises a pattern formed by the resist pattern. The method for forming a semiconductor device comprises a step for forming a resist pattern on an underlying layer by the aforementioned manufacturing method, and a step for patterning the underlying layer by etching using the resist pattern as a mask.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: December 16, 2008
    Assignee: Fujitsu Limited
    Inventors: Junichi Kon, Ei Yano
  • Patent number: 7459261
    Abstract: 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: Grant
    Filed: December 19, 2005
    Date of Patent: December 2, 2008
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Youichi Ohsawa, Seiichiro Tachibana
  • Patent number: 7449573
    Abstract: A compound which generates a sulfonic acid having one or more —SO3H groups and one or more —SO2— bonds upon irradiation with an actinic ray or a radiation; a photosensitive composition containing the compound; and a method of pattern formation with the photosensitive composition.
    Type: Grant
    Filed: February 14, 2005
    Date of Patent: November 11, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Kenji Wada, Kaoru Iwato
  • Patent number: 7419759
    Abstract: 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: Grant
    Filed: May 27, 2005
    Date of Patent: September 2, 2008
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Kyoung-Mi Kim, Jae-Ho Kim, Yeu-Young Youn, Youn-Kyung Wang
  • Patent number: 7416832
    Abstract: 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: Grant
    Filed: March 28, 2005
    Date of Patent: August 26, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daisuke Kawana, Tomotaka Yamada, Takayuki Hosono, Koki Tamura
  • Patent number: 7396899
    Abstract: The present invention provides a sulfonium salt of the formula (Ia) a polymeric compound comprising a structural unit of the formula (Ib) and a chemical amplification type positive resist composition comprising (A) an acid generator comprising at least one compound selected from the group consisting of a sulfonium salt of the formula (Ia), a polymeric compound comprising a structural unit of the formula (Ib), and a sulfonium salt of the formula (Ic); and (B) resin which contains a structural unit having an acid labile group and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid.
    Type: Grant
    Filed: December 22, 2006
    Date of Patent: July 8, 2008
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Airi Yamada, Yasunori Uetani, Akira Kamabuchi
  • Patent number: 7396633
    Abstract: With the damascene process in which an interconnection is formed using a conventional chemically amplified positive photoresist composition, there arises a problem that the photoresist within the via hole (as well as in its vicinity) may remain even after the exposure and the development are carried out. The present invention relates to a chemically amplified resist composition comprising, at least, a photo acid generator, a quencher and a salt having a buffering function for an acid which is generated from the acid generator by irradiation, wherein the salt having the buffering function for the acid generated from the acid generator is a salt derived from a long chain alkylbenzenesulfonic acid or a long chain alkoxybenzenesulfonic acid and an organic amine that is a basic compound.
    Type: Grant
    Filed: June 23, 2004
    Date of Patent: July 8, 2008
    Assignees: NEC Electronics Corporation, Shin-Etsu Chemical Co., Ltd.
    Inventors: Seiji Nagahara, Satoshi Watanabe, Kazunori Maeda
  • Patent number: 7390613
    Abstract: The present application relates to a compound of formula Ai Xi Bi where Ai and Bi are each individually an organic onium cation; and Xi is anion of the formula ?O3S—CF2CF2OCF2CF2—SO3?. The compounds are useful as photoactive materials.
    Type: Grant
    Filed: December 4, 2006
    Date of Patent: June 24, 2008
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: M. Dalil Rahman, David L. Rentkiewicz
  • Patent number: 7390609
    Abstract: 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: Grant
    Filed: March 3, 2004
    Date of Patent: June 24, 2008
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Anthony Zampini, Tao Zhang, Jaihyoung Lee
  • Patent number: 7387865
    Abstract: 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: Grant
    Filed: July 20, 2004
    Date of Patent: June 17, 2008
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sung-ouk Jung, Seung-ju Seo, Jae-chan Park
  • Patent number: 7381516
    Abstract: A photoreactive composition comprises (a) at least one reactive species that is capable of undergoing an acid- or radical-initiated chemical reaction; and (b) a photoinitiator system comprising photochemically-effective amounts of (1) at least one type of semiconductor nanoparticle quantum dot that has at least one electronic excited state that is accessible by absorption of two or more photons, and (2) a composition, different from said reactive species, that is capable of interacting with the excited state of the semiconductor nanoparticle quantum dot to form at least one reaction-initiating species.
    Type: Grant
    Filed: October 2, 2002
    Date of Patent: June 3, 2008
    Assignee: 3M Innovative Properties Company
    Inventors: David S. Arney, Catherine A. Leatherdale, Manoj Nirmal
  • Patent number: 7368218
    Abstract: A polymer which is obtained from a combination of (meth)acrylate having a bridged ring lactone group and (meth)acrylate having an acid leaving group with a hexafluoroalcohol group is used as a base resin to formulate a positive resist composition which 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. The composition also has excellent dry etching resistance.
    Type: Grant
    Filed: April 8, 2005
    Date of Patent: May 6, 2008
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Tatsushi Kaneko
  • Patent number: 7358029
    Abstract: 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: Grant
    Filed: September 29, 2005
    Date of Patent: April 15, 2008
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Phillip Joe Brock, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 7354692
    Abstract: A class of lithographic photoresist combinations is disclosed which is suitable for use with visible light and does not require a post-exposure bake step. The disclosed photoresists are preferably chemical amplification photoresists and contain a photosensitizer having the structure of formula (I): where Ar1 and Ar2 are independently selected from monocyclic aryl and monocyclic heteroaryl, R1 and R2 may be the same or different, and have the structure —X—R3 where X is O or S and R3 is C1-C6 hydrocarbyl or heteroatom-containing C1-C6 hydrocarbyl, and R4 and R5 are independently selected from the group consisting of hydrogen and —X—R3, or, if ortho to each other, may be taken together to form a five- or six-membered aromatic ring, with the proviso that any heteroatom contained within Ar1, Ar2, or R3 is O or S. The use of the disclosed photoresists, particularly for the manufacture of holographic diffraction gratings, is also disclosed.
    Type: Grant
    Filed: May 9, 2005
    Date of Patent: April 8, 2008
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Daniel Joseph Dawson, Carl E. Larson, Gregory Michael Wallraff
  • Patent number: 7351515
    Abstract: 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: Grant
    Filed: September 16, 2004
    Date of Patent: April 1, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Shoichiro Yasunami, Kenji Wada, Kunihiko Kodama, Kenichiro Sato
  • Patent number: 7344821
    Abstract: A positive resist composition for use with an electron beam, an EUV light or an X ray, the positive resist composition comprising: (A) at least one compound that generates an acid upon treatment with one of an actinic ray and radiation; and (B) a resin that increases a solubility of the resin (B) in an alkaline developer by an action of an acid, wherein the resin (B) comprises a repeating unit having an alicyclic group connected with a fluorine-substituted alcohol residue; and a pattern formation method using the composition.
    Type: Grant
    Filed: March 28, 2005
    Date of Patent: March 18, 2008
    Assignee: FUJIFILM Corporation
    Inventor: Kazuyoshi Mizutani
  • Patent number: 7338748
    Abstract: The present invention provides a planographic printing plate precursor including on a support a photosensitive layer that contains a polymerizable composition containing a specific binder polymer having a repeating unit of formula (I), an infrared absorbent, a polymerization initiator and a polymerizable compound, wherein R1 represents a hydrogen atom or a methyl group; R2 represents a linking group which includes two or more atoms selected from a carbon atom, a hydrogen atom, an oxygen atom, a nitrogen atom and a sulfur atom and has a number of atoms of 2 to 82; A represents an oxygen atom or —NR3— in which R3 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; and n represents an integer of 1 to 5. The invention also provides a planographic printing plate precursor provided with a specific photosensitive layer with respect to an alkaline developer.
    Type: Grant
    Filed: September 30, 2003
    Date of Patent: March 4, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Atsushi Sugasaki, Kazuto Kunita, Kazuhiro Fujimaki
  • Patent number: 7335454
    Abstract: 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: Grant
    Filed: December 12, 2002
    Date of Patent: February 26, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Shinichi Kanna, Kazuyoshi Mizutani, Kunihiko Kodama, Tomoya Sasaki
  • Patent number: 7335464
    Abstract: A water-soluble resin composition of the present invention comprises at least a water-soluble resin, an acid generator capable of generating an acid by heating and a solvent containing water. The water-soluble resin composition is applied on a highly water-repellant resist pattern 3 formed by a resist such as an ArF-responsive radiation sensitive resin composition on a substrate 1 to form a coated layer 4 thereon. The resist pattern 3 and the coated layer 4 are heat-treated to form a developer-insoluble modified coated layer 5 in the vicinity of a surface of the resist pattern 3. The coated layer is developed and the resist pattern thickened by the modified layer 5 is formed. The modified layer is a layer with sufficient thickness and is able to be formed with a high dimensional controllability in a highly water-repellant resist pattern such as ArF-responsive radiation sensitive resin composition.
    Type: Grant
    Filed: February 16, 2004
    Date of Patent: February 26, 2008
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Yusuke Takano, Sung-Eun Hong
  • Patent number: 7326517
    Abstract: A photosensitive composition containing: (A) a sensitizing dye; (B) a photopolymerization initiator; (c) a polymerizable compound having an ethylenically unsaturated bond; and (D) a polymer binder, wherein the photopolymerization initiator exhibits a reaction rate constant with a semiquinone radical anion in the range of 2.0×102 to 1.0×108 (mol?1·l·s?1).
    Type: Grant
    Filed: April 4, 2005
    Date of Patent: February 5, 2008
    Assignee: Konica Minolta Medical & Graphic, Inc.
    Inventor: Toshiyuki Matsumura
  • Patent number: 7314701
    Abstract: 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: Grant
    Filed: October 7, 2003
    Date of Patent: January 1, 2008
    Assignee: JSR Corporation
    Inventors: Kenichi Yokoyama, Fumihisa Miyajima, Tomoki Nagai, Eiji Yoneda
  • Patent number: 7303852
    Abstract: 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: Grant
    Filed: February 27, 2003
    Date of Patent: December 4, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Tomohiro Kobayashi, Youichi Ohsawa
  • Patent number: 7303855
    Abstract: An undercoat-forming material comprising a novolak resin having a fluorene or tetrahydrospirobiindene structure, an organic solvent, an acid generator, and a crosslinker, optionally combined with an intermediate layer having an antireflective effect, has an absorptivity coefficient sufficient to provide an antireflective effect at a thickness of at least 200 nm and a high etching resistance as demonstrated by slow etching rates with CF4/CHF3 and Cl2. BCl3 gases for substrate processing.
    Type: Grant
    Filed: September 30, 2004
    Date of Patent: December 4, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Satoshi Watanabe
  • Patent number: 7297464
    Abstract: 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: Grant
    Filed: June 27, 2005
    Date of Patent: November 20, 2007
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Haruaki Sakurai, Koichi Abe
  • Patent number: 7297460
    Abstract: A radiation curable ink composition comprising at least one initiator and at least one polyhedral oligomeric silsesquioxane (POSS) represented by the following empirical formula [R(SiO1.5)]n wherein n=4, 6, 8, 10, 12, 14, 16 and larger and each R is independently hydrogen, an inorganic group, an alkyl group, an alkylene group, an aryl group, an arylene group, or non-heterocyclic group-containing organo-functional derivatives of alkyl, alkylene, aryl or arylene groups; and a process for obtaining a colourless, monochrome or multicolour ink jet image comprising the steps of jetting one or more streams of ink droplets having the above-mentioned composition onto an ink-jet ink receiver material, and subjecting the obtained image to radiation curing.
    Type: Grant
    Filed: February 9, 2004
    Date of Patent: November 20, 2007
    Assignee: Agfa-Gevaert
    Inventors: Luc Vanmaele, Johan Loccufier, Roland Claes
  • Patent number: 7294450
    Abstract: A production process of a chemical amplification-type resist composition, which is a process for producing a chemical amplification-type composition comprising: (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (B) a resin of which solubility in an alkali developer is changed under an action of an acid; (C) a basic compound; (D) a surfactant; and (E) a solvent, the production process comprising: preparing a solution containing the component (A); and mixing the solution containing the component (A) with the components (B) to (E), and a chemical amplification-type resist composition produced by the production process.
    Type: Grant
    Filed: July 27, 2006
    Date of Patent: November 13, 2007
    Assignee: FUJIFILM Corporation
    Inventor: Shinji Tarutani
  • Patent number: 7285375
    Abstract: Disclosed is a light sensitive composition containing a compound A having a group capable of undergoing radical polymerization, a compound B having a group capable of undergoing cationic polymerization, a photopolymerization initiator C, and a polymer binder D, the light sensitive composition being characterized in that the photopolymerization initiator C comprises an iron-arene complex and a halogenated alkyl group-containing compound.
    Type: Grant
    Filed: May 31, 2004
    Date of Patent: October 23, 2007
    Assignee: Konica Minolta Medical & Graphic, Inc.
    Inventors: Toshiyuki Matsumura, Norio Miura
  • Patent number: 7282319
    Abstract: A photoresist composition for preventing exposing failures and a method of forming a pattern using the same are disclosed. The photoresist composition preferably comprises about 0.1% to about 0.5% by weight of a photo acid generator, and about 2% to about 10% by weight of a polymer resin, the PAG including a monophenyl sulfonium compound, a triphenyl sulfonium compound or a mixture thereof. The footing phenomenon and the top loss of a pattern are sufficiently prevented.
    Type: Grant
    Filed: May 31, 2005
    Date of Patent: October 16, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Kyoung-Mi Kim, Yeu-Young Youn, Youn-Kyung Wang, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim
  • Patent number: 7282318
    Abstract: 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: Grant
    Filed: June 24, 2004
    Date of Patent: October 16, 2007
    Assignee: Hynix Semiconductor Inc.
    Inventor: Jae Chang Jung
  • Patent number: 7279255
    Abstract: A radiation-sensitive composition includes a radically polymerizable component and a borate initiator composition capable of generating radicals sufficient to initiate polymerization of the radically polymerizable component upon exposure to imaging radiation. This composition also includes a radiation absorbing compound (such as an IR-sensitive dye), a polymeric binder comprising a polymer backbone to which is directly or indirectly linked a pendant group comprising a reactive vinyl group, and a primary additive that is a poly(alkylene glycol) or an ether or ester thereof that has a number average molecular weight of from about 200 and up to 4000 and comprises from about 2 to about 50 weight % based on the total composition solids content. This composition can be used to prepare a negative-working imageable element that can be imaged at relatively low energy and developed without a preheat step.
    Type: Grant
    Filed: February 7, 2006
    Date of Patent: October 9, 2007
    Assignee: Eastman Kodak Company
    Inventors: Ting Tao, Scott A. Beckley
  • Patent number: 7270931
    Abstract: 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: Grant
    Filed: October 6, 2003
    Date of Patent: September 18, 2007
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Wu-Song Huang, Arpan P. Mahorowila, Wayne Moreau, Dirk Pfeiffer, Ratnam Sooriyakumaran
  • Patent number: 7270936
    Abstract: 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: Grant
    Filed: July 6, 2005
    Date of Patent: September 18, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventor: Sang-Jun Choi
  • Patent number: 7270916
    Abstract: Disclosed is a recording medium comprising a recording layer including a photo-acid generating agent that generates an acid upon irradiation with an actinic radiation and a polymer having a polymerizable substituent group bonded to a main chain of the polymer via a functional group that cleaves in the presence of the acid.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: September 18, 2007
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Naoko Kihara, Urara Ichihara, legal representative, Akiko Hirao, Kazuki Matsumoto, Hideyuki Nishizawa, Katsutaro Ichihara, deceased
  • Patent number: 7264918
    Abstract: 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: Grant
    Filed: March 24, 2004
    Date of Patent: September 4, 2007
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kotaro Endo, Masaaki Yoshida, Taku Hirayama, Hiromitsu Tsuji, Toshiyuki Ogata, Mitsuru Sato