Binder Containing Patents (Class 430/905)
  • Patent number: 7601480
    Abstract: The present application relates to a compound of formula where X is selected from the group CF3SO3, C4F9SO3, N(SO2C2F5)2, N(SO2CF3SO2C4F9), N(SO2C3F7)2, N(SO2C4F9)2, CF3CHFO(CF2)2SO3, and CH3CH2CH2O(CF2)4SO3. A photoresist composition comprising a polymer containing an acid labile group, the above compounds, and one or more additional photoacid generators is also provided for.
    Type: Grant
    Filed: December 20, 2006
    Date of Patent: October 13, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: M. Dalil Rahman, Takanori Kudo
  • Patent number: 7598017
    Abstract: A negative resist composition including: a fluorine-containing resin component (F) containing a structural unit (f1) represented by a general formula (f1-0) shown below, and a structural unit (f2) having an alkali-soluble group, an alkali-soluble resin component (A) excluding the fluorine-containing resin component (F), an acid generator component (B) that generates acid upon exposure, and a cross-linking component (C). [wherein, R7 represents a fluorinated alkyl group, and a represents either 0 or 1.
    Type: Grant
    Filed: October 24, 2008
    Date of Patent: October 6, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Jun Iwashita, Kazuhito Sasaki, Sho Abe
  • Patent number: 7598014
    Abstract: A negative thick film photoresist composition with improved alkali developability is provided. The composition comprises: (A) a resin component containing (a) from 61 to 90% by weight of a structural unit derived from a cyclic alkyl (meth)acrylate ester, and (b) a structural unit derived from a radical polymerizable compound containing a hydroxyl group, (B) a polymerizable compound containing at least one ethylenic unsaturated double bond, (C) a photopolymerization initiator, and (D) an organic solvent.
    Type: Grant
    Filed: November 18, 2004
    Date of Patent: October 6, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yasushi Washio, Koji Saito
  • Patent number: 7595143
    Abstract: A photoresist composition includes about 10 to about 70% by weight of a binder resin including a phenol-based polymer, about 0.5 to about 10% by weight of a photo-acid generator, about 1 to about 20% by weight of a cross-linker, about 0.1 to about 5% by weight of a dye and about 10 to about 80% by weight of a solvent. The photoresist composition may be applied to, for example, a method of manufacturing a TFT substrate.
    Type: Grant
    Filed: August 22, 2006
    Date of Patent: September 29, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Jeong-Min Park, Hi-Kuk Lee, Hyoc-Min Youn, Ki-Hyuk Koo, Byung-Uk Kim
  • Patent number: 7592128
    Abstract: The present invention relates to negative-working imageable elements that can be used for the manufacture of printing plates. These imageable elements can be developed on on-press by the action of a lithographic printing ink used in combination with either water or a fountain solution. The imageable elements comprise an imageable layer that is not removable in water or fountain solution alone. The imageable layer includes a free radically polymerizable compound, a free radical initiator composition, an infrared radiation absorbing compound, and a polymeric binder comprising poly(alkylene oxide) pendant groups, and preferably additionally pendant cyano groups.
    Type: Grant
    Filed: August 7, 2006
    Date of Patent: September 22, 2009
    Assignee: Eastman Kodak Company
    Inventors: Jianbing Huang, Kevin B. Ray, Scott A. Beckley
  • Patent number: 7592118
    Abstract: A positive resist composition, includes: (B) a resin containing a repeating unit represented by formula (Ia) or (Ib) as defined in the specification, which decomposes under an action of an acid to increase a solubility of the resin (B) in an aqueous alkali solution; and (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation, and a pattern forming method uses the composition.
    Type: Grant
    Filed: March 24, 2008
    Date of Patent: September 22, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Kazuyoshi Mizutani, Shuji Hirano, Shinichi Sugiyama
  • Patent number: 7592125
    Abstract: New positive photoresist compositions are provided that contain a photoactive component and blend of at least two distinct resins: i) a first resin that comprises carbocyclic aryl units with hetero substitution (particularly hydroxy or thio) and ii) a second cross-linked resin. Preferred photoresists of the invention can be imaged at short wavelengths, such as sub-200 nm, particularly 193 nm.
    Type: Grant
    Filed: January 19, 2006
    Date of Patent: September 22, 2009
    Assignee: Rohm and Haas Electric Materials LLC
    Inventors: Yasuhiro Suzuki, Cheng-Bai Xu
  • Patent number: 7592126
    Abstract: A positive resist composition comprising: (A) a resin insoluble or sparingly soluble in an alkali but capable of decomposing under an action of an acid to increase a solubility in an alkali developer, the resin having a ?-(meth)acroyloxy-?-butyrolactone repeating unit represented by the following formula (1) containing a lactone ring which may have a substituent; and (B) a compound capable of generating an organic acid represented by the formula (2), (3), (3?), (4) or (5) as defined herein upon irradiation of actinic rays or radiation.
    Type: Grant
    Filed: March 17, 2006
    Date of Patent: September 22, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Fumiyuki Nishiyama
  • Patent number: 7592121
    Abstract: An antireflection film that has sufficient antireflection capability and antifouling property and is improved in scratch resistance, and a process for producing an antireflection film with considerably high productivity are provided, which is an antireflection film comprising a transparent support, a hard coat layer and a low refractive index layer, in this order, wherein the hard coat layer includes a polymerized product of (A) an ethylene oxide or propylene oxide adduct of a polyfunctional acrylate monomer and (B) a polyfunctional acrylate monomer having no oxide adduct.
    Type: Grant
    Filed: January 22, 2004
    Date of Patent: September 22, 2009
    Assignee: Fujifilm Corporation
    Inventor: Yuuzou Muramatsu
  • Patent number: 7588878
    Abstract: An image forming medium includes a substrate and an imaging layer coated on or impregnated into the substrate, where the imaging layer includes a photoacid generator and an acid-base indicator. In the image forming medium, irradiation of the imaging layer causes the photoacid generator to generate an acid that reacts with the acid-base indicator to produce an image.
    Type: Grant
    Filed: June 13, 2007
    Date of Patent: September 15, 2009
    Assignee: Xerox Corporation
    Inventors: Gabriel Iftime, Tyler B. Norsten, Peter M. Kazmaier
  • Patent number: 7588876
    Abstract: A resist material includes a base polymer containing a compound having a unit represented by a general formula of the following Chemical Formula 1: 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; R5 is a hydrogen 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, or a protecting group released by an acid; and R6 is a group having a cyclic ester compound, a group having an alicyclic compound including a hydroxyl group or a group having a compound including hexafluoroisopropyl alcohol.
    Type: Grant
    Filed: May 13, 2005
    Date of Patent: September 15, 2009
    Assignee: Panasonic Corporation
    Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Hirokazu Imori, Toshiaki Fukuhara
  • Patent number: 7585610
    Abstract: The present invention provides a resist pattern thickening material, which can utilize ArF excimer laser light; which, when applied over a resist pattern to be thickened e.g., in form of lines and spaces pattern, can thicken the resist pattern to be thickened regardless of the size of the resist pattern to be thickened; and which is suited for forming a fine space pattern or the like, exceeding exposure limits. The present invention also provides a process for forming a resist pattern and a process for manufacturing a semiconductor device, wherein the resist pattern thickening material of the present invention is suitably utilized.
    Type: Grant
    Filed: January 20, 2006
    Date of Patent: September 8, 2009
    Assignee: Fujitsu Limited
    Inventors: Koji Nozaki, Miwa Kozawa, Takahisa Namiki
  • Patent number: 7585611
    Abstract: A photocurable and thermosetting resin composition comprising (A) a carboxylic acid-containing photosensitive resin having at least one carboxyl group and at least two ethylenically unsaturated bonds in its molecule, (B) a filler, (C) a photopolymerization initiator, (D) a diluent, and (E) a compound having at least two cyclic ether groups and/or cyclic thioether groups in its molecule, wherein the difference between the refractive index of the carboxylic acid-containing photosensitive resin (A) and that of the filler (B) is 0.20 or less, and the average grain diameter of the filler (B) is 0.5 to 0.05 ?m, and wherein the photo-curing and thermosetting resin composition can be developed by a diluted alkali solution, and can be pattern-formed by a laser oscillation light source of 350 to 420 nm in wavelength.
    Type: Grant
    Filed: January 5, 2007
    Date of Patent: September 8, 2009
    Assignee: Taiyo Ink Mfg. Co., Ltd.
    Inventors: Kenji Kato, Gen Itokawa
  • Patent number: 7582412
    Abstract: Multilayer photoresist systems are provided. In particular aspects, the invention relates to underlayer composition for an overcoated photoresist, particularly an overcoated silicon-containing photoresist. Preferred underlayer compositions comprise one or more resins or other components that impart etch-resistant and antireflective properties, such as one or more resins that contain phenyl or other etch-resistant groups and anthracene or other moieties that are effective anti-reflective chromophores for photoresist exposure radiation.
    Type: Grant
    Filed: November 20, 2003
    Date of Patent: September 1, 2009
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: James F. Cameron, Dana A. Gronbeck, George G. Barclay
  • Patent number: 7582398
    Abstract: An image forming medium includes a substrate and an imaging layer coated on or impregnated into the substrate, where the imaging layer includes a photobase generator and a coupling agent. In the image forming medium, irradiation of the imaging layer cause the photobase generator to generate a base that reacts with the coupling agent to produce an image.
    Type: Grant
    Filed: June 13, 2007
    Date of Patent: September 1, 2009
    Assignee: Xerox Corporation
    Inventors: Gabriel Iftime, Peter M. Kazmaier, Tyler B. Norsten
  • Patent number: 7582407
    Abstract: Single- and multi-layer positive-working imageable elements include an ink receptive outer layer includes a primary polymeric binder that is a poly(vinyl phenol) or a phenolic polymer having certain acidic groups. The use of this type of polymeric binder makes the imaged elements developable in low pH (11 or less) alkaline developers.
    Type: Grant
    Filed: July 9, 2007
    Date of Patent: September 1, 2009
    Assignee: Eastman Kodak Company
    Inventors: Celin Savariar-Hauck, Alan S. Monk, Gerhard Hauck
  • Patent number: 7579132
    Abstract: The present invention provides a salt represented by the formula (I): wherein X represents an n-valent connecting group, Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, n represents 2 or 3, and A+ represents an organic counter ion. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).
    Type: Grant
    Filed: June 4, 2007
    Date of Patent: August 25, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukako Harada, Isao Yoshida, Satoshi Yamaguchi
  • Patent number: 7572560
    Abstract: An image forming medium includes a substrate, and an imaging layer coated on or impregnated into said substrate, wherein the imaging layer includes an imaging composition including a photochromic or photochromic-thermochromic material dissolved or dispersed in a solvent or polymeric binder, wherein the imaging composition is imageable by light of a first wavelength and erasable in a short time period by a combination of heat and light of a second wavelength such that simultaneous erase with heat and light of the second wavelength is faster than erase by heat alone and exhibits a reversible transition between a colorless and a colored state.
    Type: Grant
    Filed: June 13, 2007
    Date of Patent: August 11, 2009
    Assignee: Xerox Corporation
    Inventors: Peter M. Kazmaier, Gabriel Iftime, Tyler B. Norsten, Barkev Keoshkerian, Naveen Chopra
  • Patent number: 7569325
    Abstract: A photoresist monomer having a sulfonyl group, a polymer thereof and a photoresist composition containing the same are disclosed. The photoresist monomer is represented by following Formula. wherein, R* is a hydrogen atom or a methyl group, R1 and R2 are independently a C1˜C20 alkyl group, a C4˜C20 cycloalkyl group, a C6˜C20 aryl group or a C7˜C20 arylalkyl group, one of R1 and R2 may not exist, and R1 and R2 can be connected to form a ring.
    Type: Grant
    Filed: October 24, 2007
    Date of Patent: August 4, 2009
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jung-Youl Lee, Geun-Jong Yu, Sang-Jung Kim, Jae-Woo Lee, Deog-Bae Kim, Jae-Hyun Kim
  • Patent number: 7569328
    Abstract: The present invention provides a resin composition that includes (A) a polymer compound that has, on a side chain of a main chain polymer, through a linkage group containing a hydrogen-bonding group and a ring structure, a terminal ethylenic unsaturated bond, and is soluble or swelling in water or an alkali aqueous solution, and (B) a compound that generates radicals when exposed to light or heat. The invention further provides a thermo/photosensitive composition that includes (A?) a polymer compound that has a non-acidic hydrogen-bonding group on a side chain and is soluble or swelling in water or an alkali aqueous solution, and (B?) a compound that generates radicals when exposed to light or heat.
    Type: Grant
    Filed: August 12, 2003
    Date of Patent: August 4, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Kazuhiro Fujimaki
  • Patent number: 7569323
    Abstract: A resist protective coating material is provided comprising an ?-trifluoromethylacrylic acid/norbornene copolymer having cyclic perfluoroalkyl groups as pendant. In a pattern-forming process, the material forms on a resist film a protective coating which is water-insoluble, dissolvable in alkaline developer and immiscible with the resist film, allowing for effective implementation of immersion lithography.
    Type: Grant
    Filed: July 26, 2006
    Date of Patent: August 4, 2009
    Assignees: Shin-Etsu Chemical Co., Ltd., Panasonic Corporation, Central Glass Co., Ltd.
    Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai, Masayuki Endo, Masaru Sasago, Haruhiko Komoriya, Michitaka Ootani, Satoru Miyazawa, Kazuhiko Maeda
  • Patent number: 7563556
    Abstract: A positive-working imageable element comprises inner and outer layers and an infrared radiation absorbing compound such as an IR absorbing dye. The ink receptive outer layer includes a phenolic polymeric binder that is soluble in a developer having a pH of from about 7 to about 11. The use of this type of polymeric binder reduces residue in the developer as elements are processed.
    Type: Grant
    Filed: November 17, 2006
    Date of Patent: July 21, 2009
    Assignee: Kodak Graphic Communications GmbH
    Inventors: Celin Savariar-Hauck, Gerhard Hauck
  • Patent number: 7556910
    Abstract: The present invention relates to a photosensitive composition comprising a triazine-based photoactive compound containing oxime ester. The photosensitive composition according to the present invention has good sensitivity, retention rate, mechanical strength, heat resistance, chemical resistance and developing durability since it contains, as photopolymerization initiator, a compound having an oxime ester group and a triazine group in one molecule and thus effectively absorbs UV radiation. Therefore, the photosensitive composition according to the present invention is advantageous not only in curing of materials for color filters, resin black matrixes, column spacers, overcoats and passivation films of liquid crystal displays, but also in high temperature process characteristics.
    Type: Grant
    Filed: November 29, 2006
    Date of Patent: July 7, 2009
    Assignee: LF Chem, Ltd.
    Inventors: Sung Hyun Kim, Kyung Jun Kim, Dong Chang Choi, Jeong Ae Yoon, Hee Kwan Park, Geun Young Cha, Keon Woo Lee, Il Eok Kwon, Dong Kung Oh, Jong Hyun Park, Xiang Li Li, Han Soo Kim, Min Young Lim, Chang Ho Cho
  • Patent number: 7553603
    Abstract: An image forming medium includes a substrate and an imaging layer coated on or impregnated into the substrate, where the imaging layer includes a photobase generator and an acid-base indicator. In the image forming medium, irradiation of the imaging layer causes the photobase generator to generate a base that reacts with the acid-base indicator to produce an image.
    Type: Grant
    Filed: June 13, 2007
    Date of Patent: June 30, 2009
    Assignee: Xerox Corporation
    Inventors: Gabriel Iftime, Tyler B. Norsten, Peter M. Kazmaier
  • Patent number: 7550248
    Abstract: The object of the present invention is to provide a resist pattern thickening material, etc. which, when coated over a resist pattern formed of ArF resist material, etc., can efficiently thicken the resist pattern such as lines and spaces pattern, etc. regardless of the composition of ArF resist material, and the like; which can easily control the thickening amount of resist pattern by process condition; and which can easily and efficiently form a fine space pattern beyond the exposure (resolution) limits of light sources of the exposure devices at low cost. The resist pattern thickening material of the present invention comprises a solubilizer which melts the resist pattern at the temperature near its melting point and- a water-soluble element. The process for forming a resist pattern of the present invention comprises forming a resist pattern and coating a resist pattern thickening material of the present invention over the surface of the resist pattern.
    Type: Grant
    Filed: December 28, 2005
    Date of Patent: June 23, 2009
    Assignee: Fujitsu Limited
    Inventors: Takahisa Namiki, Koji Nozaki, Miwa Kozawa
  • Patent number: 7550249
    Abstract: Base soluble polymer comprising at least one sulfonyl group where at least one carbon atom at ?-position and/or ?-position and/or ?-position with respect to the sulfonyl group has a hydroxyl group, where the hydroxyl group is protected or unprotected are described.
    Type: Grant
    Filed: March 10, 2006
    Date of Patent: June 23, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: David Abdallah, Francis Houlihan
  • Patent number: 7550250
    Abstract: A positive resist composition, which comprises: (A) a resin having a monocyclic or polycyclic alicyclic hydrocarbon structure, of which solubility in an alkali developer increases under an action of an acid; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (C) a resin having a repeating unit represented by formula (C) as defined in the specification; and (D) a solvent, wherein a content of the resin as the component (C) is from 0.1 to 20 mass % based on a solid content of the positive resist composition, and a pattern forming method using the same.
    Type: Grant
    Filed: December 27, 2006
    Date of Patent: June 23, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Hiromi Kanda
  • Patent number: 7544461
    Abstract: A near infrared ray activation type positive resist composition comprising (A) a vinyl-based polymer having a monomer unit having an alkali-soluble group blocked by an ether having an alkenyl group next to an ether oxygen, (B) a photothermal converting substance generating heat by a light in the near infrared region, (C) a thermal acid generator generating an acid by heat, can provide a near infrared ray activation type positive resist composition which can be subjected to an exposure treatment in a complete bright room such as under a white light and the like, gives desired sensitivity and resolution, and of which baking treatment conditions can be relaxed or a baking treatment can be omitted, and a pattern formation method using the same.
    Type: Grant
    Filed: July 22, 2005
    Date of Patent: June 9, 2009
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Genji Imai, Toshikazu Murayama, Katsuhiro Ito, Haruhumi Hagino
  • Patent number: 7544460
    Abstract: A resist composition is disclosed that enables formation of a favorable resist pattern using a shrink process in which, following formation of the resist pattern, a treatment such as heating is used to narrow the resist pattern, and also disclosed are a laminate and a method for forming a resist pattern that use such a resist composition. This resist composition includes a resin component (A) that displays changed alkali solubility under the action of acid, and an acid generator component (B) that generates acid on exposure. The component (A) contains structural units derived from a (meth)acrylate ester, and exhibits a glass transition temperature that falls within a range from 120 to 170° C.
    Type: Grant
    Filed: July 7, 2004
    Date of Patent: June 9, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Kazuhito Sasaki, Satoshi Fujimura, Takeshi Iwai
  • Patent number: 7541131
    Abstract: The invention provides a resist composition for use in the production process of a semiconductor such as IC, in the production of a circuit substrate of liquid crystal, thermal head and the like or in other photofabrication processes, a compound for use in the resist composition and a pattern forming method using the resist composition, which are a resist composition comprising (A) a sulfonium salt represented by the following formula (I); and a pattern forming method using the resist composition: wherein R1 represents an alkyl group or an aryl group, R2 to R9 each independently represents a hydrogen atom or a substituent and may combine with each other to form a ring, Z represents an electron-withdrawing divalent linking group, Xn? represents an n-valent anion, n represents an integer of 1 to 3, and m represents the number of anions necessary for neutralizing the electric charge.
    Type: Grant
    Filed: February 17, 2006
    Date of Patent: June 2, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Yasutomo Kawanishi
  • Patent number: 7541138
    Abstract: A resist composition which is stable relative to solvents used in immersion lithography processes and displays excellent sensitivity and resist pattern profile, and a method of forming a resist pattern that uses such a resist composition are provided. The resist composition is in accordance with predetermined parameters, or is a positive resist composition comprising a resin component (A) which contains an acid dissociable, dissolution inhibiting group and displays increased alkali solubility under the action of acid, an acid generator component (B), and an organic solvent (C), wherein the component (A) contains a structural unit (a1) derived from a (meth)acrylate ester containing an acid dissociable, dissolution inhibiting group, but contains no structural units (a0), including structural units (a0-1) containing an anhydride of a dicarboxylic acid and structural units (a0-2) containing a phenolic hydroxyl group.
    Type: Grant
    Filed: January 10, 2007
    Date of Patent: June 2, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Taku Hirayama, Hideo Hada, Satoshi Fujimura, Takeshi Iwai, Mitsuru Sato, Ryoichi Takasu, Toshikazu Tachikawa, Jun Iwashita, Keita Ishiduka, Tomotaka Yamada, Toshikazu Takayama, Masaaki Yoshida
  • Patent number: 7541119
    Abstract: An image forming medium includes a substrate and an imaging layer coated on or impregnated into said substrate, where the imaging layer includes a photochromic material dispersed in an ionomer, optionally with an additional polymeric binder, and where the photochromic material exhibits a reversible transition between a colorless state and a colored state in response to heat and optional light.
    Type: Grant
    Filed: June 13, 2007
    Date of Patent: June 2, 2009
    Assignee: Xerox Corporation
    Inventors: Tyler B. Norsten, Gabriel Iftime, Peter M. Kazmaier
  • Patent number: 7541133
    Abstract: A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid, and (B) an acid generator. The resin (A) is a polymer comprising tertiary alkyl protective group units having a hydrophobic tetracyclo[4.4.0.12,5.17,10]-dodecane structure, hydroxyadamantane units, monocyclic lactone units, and carboxylic acid units. The acid generator (B) is a specific sulfonium salt compound.
    Type: Grant
    Filed: November 20, 2007
    Date of Patent: June 2, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Seiichiro Tachibana, Katsuhiro Kobayashi
  • Patent number: 7537879
    Abstract: The present invention relates to a novel chemically amplified photoresist, which is sensitive to wavelengths between 300 nm and 100 nm, and comprises a) a novel polymer comprising a sulfone group pendant from a polymer backbone that is insoluble in an aqueous alkaline solution and comprises at least one acidic moiety protected with acid labile group, and b) a compound capable of producing an acid upon irradiation. The invention also relates to a process of imaging the novel positive photoresist composition.
    Type: Grant
    Filed: November 22, 2004
    Date of Patent: May 26, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Francis M. Houlihan, Ralph R. Dammel, Andrew R. Romano, Munirathna Padmanaban, M. Dalil Rahman
  • Patent number: 7537880
    Abstract: To a resist composition, an alkali-soluble polymer having fluorinated ester-containing lactone units incorporated therein is included as an additive. The resist composition forms a resist film having a reduced contact angle after development. The resist film prevents water penetration during immersion lithography.
    Type: Grant
    Filed: October 3, 2007
    Date of Patent: May 26, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Takao Yoshihara, Wataru Kusaki, Tomohiro Kobayashi, Koji Hasegawa
  • Patent number: 7534548
    Abstract: A polymer for immersion lithography comprising a repeating unit represented by Formula 1 and a photoresist composition containing the same. A photoresist film formed by the photoresist composition of the invention is highly resistant to dissolution, a photoacid generator in an aqueous solution for immersion lithography, thereby preventing contamination of an exposure lens and deformation of the photoresist pattern by exposure.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: May 19, 2009
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Cheol Kyu Bok, Chang Moon Lim, Seung Chan Moon
  • Patent number: 7531288
    Abstract: A photosensitive lithographic printing plate comprising: a hydrophilic support; and a photosensitive layer containing a polymerization initiator, a chain transfer agent, a compound having an ethylenically unsaturated double bond and a polymer binder having a crosslinkable group in a side chain, wherein the chain transfer agent is a thiol compound represented by the following formula (I): in which R represents an alkyl group which may have a substituent or an aryl group which may have a substituent; and A represents an atomic group necessary for forming a 5-membered or 6-membered hetero ring containing a carbon atom together with the N?C—N linkage, and A may have a substituent.
    Type: Grant
    Filed: September 26, 2005
    Date of Patent: May 12, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Keisuke Arimura, Takahiro Goto
  • Patent number: 7531290
    Abstract: Sulfonate salts have the formula: R1SO3—CH(Rf)—CF2SO3?M+ wherein R1 is alkyl or aryl, Rf is H or trifluoromethyl, and M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: October 27, 2006
    Date of Patent: May 12, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
  • Patent number: 7527915
    Abstract: The present invention is directed to phosphorus containing (or “halogen free”) multi-layer flame retardant photoimagable compositions useful as a coverlay material in a flexible electronic circuitry package. These compositions generally contain a top layer and bottom layer adjacent to one another both being photosensitive and comprising phosphorus containing acrylates and phosphorus-containing photo-initiators mixed with a polymer binder. These compositions typically have phosphorus in the top layer in an amount between, and including, any two of the following numbers 2.0, 2.2, 2.4, 2.6, 2.8, 3.0, 3.2, 3.4, 3.6, 3.8, 4.0, 4.2, 4.4, 4.6, 4.8, 5.0, 5.2, 5.4, 5.6, 5.8, 6.0, 6.2, 6.4, 6.6, 6.8, 7.0, 7.2, 7.4, 7.6, 7.8, 8.0, 8.2, 8.4, 8.6, 8.8, 9.0, 9.2, 9.4, 9.6, 9.8, and 10.0 weight percent, and have phosphorus in the bottom layer in an amount between, and including, any two of the following numbers, 0.0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.4, 2.6, 2.8, 3.0, 3.2, 3.4, 3.6, 3.8, and 4.
    Type: Grant
    Filed: July 19, 2006
    Date of Patent: May 5, 2009
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Tsutomu Mutoh
  • Patent number: 7527912
    Abstract: Photoacid generators generate sulfonic acids of formula (1a) upon exposure to high-energy radiation. RC(?O)R1—COOCH(CF3)CF2SO3?H+??(1a) R is hydroxyl, alkyl, aryl, hetero-aryl, alkoxy, aryloxy or hetero-aryloxy, R1 is a divalent organic group which may have a heteroatom (O, N or S) containing substituent, or R1 may form a cyclic structure with R. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.
    Type: Grant
    Filed: September 27, 2007
    Date of Patent: May 5, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Koji Hasegawa, Masaki Ohashi
  • Patent number: 7524594
    Abstract: Some embodiments in accordance with the present invention relate to norbornene-type polymers and to photosensitive dielectric resin compositions formed therefrom. Other embodiments relate to films formed from such compositions and to devices, such as electrical, electronic and optoelectronic devices, that encompass such films.
    Type: Grant
    Filed: July 1, 2005
    Date of Patent: April 28, 2009
    Assignee: Promerus LLC
    Inventors: Dino Amoroso, Brian Bedwell, Andrew Bell, Edmund Elce, Rajesh Raja Puthenkovilakom, Ramakrishna Ravikiran, Robert Shick, Xiaoming Wu, Hiroaki Makabe, Yasunori Takahashi, Etsu Takeuchi, Daoji Gan, Seok Ho Kang
  • Patent number: 7524606
    Abstract: The present invention relates to a photoresist composition suitable for image-wise exposure and development as a positive photoresist comprising a positive photoresist composition and an inorganic particle material having an average particle size equal or greater than 10 nanometers, wherein the thickness of the photoresist coating film is greater than 5 microns. The positive photoresist composition can be selected from (1) a composition comprising (i) a film-forming resin having acid labile groups, and (ii) a photoacid generator, or (2) a composition comprising (i) a film-forming novolak resin, and (ii) a photoactive compound, or (3) a composition comprising (i) a film-forming resin, (ii) a photoacid generator, and (iii) a dissolution inhibitor.
    Type: Grant
    Filed: April 11, 2005
    Date of Patent: April 28, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Chunwei Chen, Ping-Hung Lu, Hong Zhuang, Mark Neisser
  • Patent number: 7521168
    Abstract: A resist composition for an electron beam, EUV or X-ray comprising (A1) a compound that has a reduction potential higher than that of diphenyl iodonium salt and generates an acid upon irradiation of an actinic ray or radiation.
    Type: Grant
    Filed: February 11, 2003
    Date of Patent: April 21, 2009
    Assignee: Fujifilm Corporation
    Inventors: Kazuyoshi Mizutani, Hyou Takahashi
  • Patent number: 7517633
    Abstract: A composition for forming a gap-filling material for lithography which, as a gap-filling material for lithography superior in planarization ability on a substrate having irregularities such as holes or trenches, causing no intermixing with a resist layer, and having a high dry etching rate as compared with the resist, is used in producing semiconductor devices by a method using the gap-filling material to cover the resist on the substrate having holes having an aspect ratio, defined as height/diameter, of 1 or more to transfer images onto the substrate by utilization of lithographic process, the composition being used to coat the substrate prior to the coating of the resist so as to planarize the substrate surface, and the composition being characterized by containing a polymer solution consisting of a polymer and a solvent.
    Type: Grant
    Filed: July 12, 2001
    Date of Patent: April 14, 2009
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Satoshi Takei, Ken-ichi Mizusawa, Yasuhisa Sone
  • Patent number: 7514201
    Abstract: A positive photosensitive composition comprising (A) an acid generator that generates an acid upon irradiation of an actinic ray or radiation, (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase solubility in an alkali developing solution, and (C) a specific basic compound.
    Type: Grant
    Filed: January 26, 2007
    Date of Patent: April 7, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Toru Fujimori
  • Patent number: 7514204
    Abstract: A resist composition comprises a polymer which increases its alkali solubility under the action of an acid as a base resin, and a copolymer comprising recurring units containing a sulfonic acid amine salt and recurring units containing at least one fluorine atom as an additive. The composition is suited for immersion lithography.
    Type: Grant
    Filed: October 23, 2007
    Date of Patent: April 7, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Wataru Kusaki, Yuji Harada, Takao Yoshihara
  • 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: 7514199
    Abstract: Provided herein are hardmask compositions for resist underlayer films, wherein in some embodiments, the hardmask compositions include (a) a first polymer prepared by the reaction of a compound of Formula 1 ?wherein n is a number of 3 to 20, with a compound of Formula 2 (R)m—Si—(OCH3)4-m??(2) ?wherein R is a monovalent organic group and m is 0, 1 or 2; (b) a second polymer that includes at least one of the structures represented by Formulae 3-6; (c) an acid or base catalyst; and (d) an organic solvent. Further provided herein are methods for producing a semiconductor integrated circuit device using a hardmask composition according to an embodiment of the present invention. In addition, provided herein are semiconductor integrated circuit devices produced by a method embodiment of the invention.
    Type: Grant
    Filed: August 22, 2006
    Date of Patent: April 7, 2009
    Assignee: Cheil Industries, Inc.
    Inventors: Dong Seon Uh, Chang Il Oh, Do Hyeon Kim, Hui Chan Yun, Jin Kuk Lee, Irina Nam, Jong Seob Kim
  • Patent number: 7514198
    Abstract: A radiation image-able coating includes a first phase including a radiation curable polymer matrix and an activator disposed in the radiation curable polymer matrix, a second phase insolubly distributed in the first phase, the second phase including a color-former, and a hybrid antenna dye package distributed in at least one of the first and second phase, wherein the hybrid antenna dye package includes at least a first antenna dye having a high extinction coefficient and a second antenna dye having a low extinction coefficient.
    Type: Grant
    Filed: August 15, 2005
    Date of Patent: April 7, 2009
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Vladek Kasperchik, Cari L. Dorsh, Makarand P. Gore
  • Patent number: 7510822
    Abstract: A stimulation sensitive composition comprising: (A) a compound represented by the specific formula which is capable of generating an acid or a radical by stimulation from the external.
    Type: Grant
    Filed: April 9, 2003
    Date of Patent: March 31, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama