Bridged Monomer Patents (Class 526/281)
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Patent number: 7335709Abstract: The invention relates to water-soluble, preferably powder-form polymer compositions which are obtained by continuous polymerization of at least one unsaturated monomer. At least one parameter that influences the polymerization is varied according to a recurrent pattern. The invention also relates to the use of the inventive polymer compositions and to a method for producing them.Type: GrantFiled: August 2, 2000Date of Patent: February 26, 2008Assignee: Ashland Licensing and Intellectual Property LLCInventors: Helmut Brehm, Hans-Georg Hartan
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Patent number: 7312285Abstract: The present invention relates to a method for preparing a cyclic olefin polymer by addition polymerization, and more particularly to a method for preparing a norbornene-based addition polymer, which comprises a step of contacting a norbornene-based monomer having an ester or acetyl group with a catalyst system comprising: a Group X transition metal compound; a compound comprising a neutral Group XV electron donor ligand having a cone angle of at least 160°; and a salt capable of offering an anion that can be weakly coordinated to the transition metal, in solvent. The norbornene-based addition polymer having an ester or acetyl group according to the present invention is transparent, has superior adhesivity and a low dielectric constant, and it generates no byproducts when attached to metal. Therefore, it can be used as an optical film, a retardation film, a protection film for a polarizer, POFs (plastic optical fiber), PCBs (printed circuit board), or insulators of electronic devices.Type: GrantFiled: July 7, 2003Date of Patent: December 25, 2007Assignee: LG Chem, Ltd.Inventors: Sung-Ho Chun, Won-Kook Kim, Sung-Cheol Yoon, Tae-Sun Lim, Heon Kim, Kyoung-Hoon Kim
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Patent number: 7300739Abstract: The present invention provides polymers that are useful in negative resist compositions. Polymers of the present invention comprise (1) a first monomer having a polar functional group; (2) a second monomer; and optionally, (3) a third monomer that imparts at least one characteristic selected from crosslinkable functionality, etch resistance, and solubility modulation. The first monomer provides an acid catalyzed polarity switch upon elimination of the polar functional group, whereas, the second monomer provides aqueous dissolution. The polymers of the present invention may be incorporated into negative resist compositions, which may also include photoacid generators, crosslinking agents, basic compounds, solvents, dissolution accelerators, photobase generators, latent basic compounds, surfactants, adhesion promoters, and anti-foaming agents.Type: GrantFiled: May 29, 2003Date of Patent: November 27, 2007Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard A. DiPietro, David R. Medeiros, Ratnam Sooriyakumaran
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Patent number: 7291689Abstract: The present invention provides norbornene-based copolymers for which one monomer is at least selected from a group consisting of norbornene and dicyclopentadiene, and the other from norbornene-based comonomers of Formula 1 shown below: In Formula 1, R1, R2 and a are defined in this specification. The present invention provides insulating elements for multi-chip packages and antireflection films for the exposure process of semiconductor fabrication using said norbornene-based copolymers. Norbornene-based copolymers according to the present invention have low dielectric constant as well as high thermal stability and excellent solubility to various organic solvents.Type: GrantFiled: May 1, 2006Date of Patent: November 6, 2007Assignee: Seoul National University Industry FoundationInventors: Jin Kyu Lee, Dong Woo Yoo, Seung Jae Yang, Kook Heon Char, Joo Hyeon Park
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Patent number: 7273915Abstract: A crosslinkable resin composition is provided which can be a forming material having excellent adhesion to metals and excellent heat resistance. The crosslinkable resin composition comprises; a cycloolefin resin (A) obtained through metathesis polymerization of a cycloolefin monomer in the presence of a compound having two or more vinyl groups in the molecule, and a radical generating agent (B). A crosslinked resin molded product is obtained by crosslinking such a crosslinkable resin composition through heating.Type: GrantFiled: August 13, 2004Date of Patent: September 25, 2007Assignee: Zeon CorporationInventor: Tomoo Sugawara
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Patent number: 7271230Abstract: The present invention provided a norbornene compound with cross-linkable groups and their derivative polymers, wherein said cross-linkable groups were olefin or epoxy groups. Norbornene polymers with cross-linkable side chain and their block copolymers as well as modified derivatives were prepared via living ring-open metathesis polymerization method. The resulting polymers with excellent solubility and optic properties had narrow molecular weight distribution, well-controlled molecular weight, small refraction ration and high transparency. They were also suitable for preparing hybrid materials with high thermal stability and chemical resistance.Type: GrantFiled: September 18, 2006Date of Patent: September 18, 2007Assignee: National Taiwan University of Science & TechnologyInventors: Der-Jang Liaw, Ching-Cheng Huang
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Patent number: 7268196Abstract: A process for producing a cycloolefin addition polymer in which one or more cycloolefin monomers can be (co)polymerized by addition polymerization with a small palladium catalyst amount to produce a cycloolefin addition (co)polymer while attaining high catalytic activity. The process for cycloolefin addition polymer production is characterized by addition-polymerizing one or more cycloolefin monomers comprising a cycloolefin compound represented by a specific formula in the presence of a multi-component catalyst comprising (a) a palladium compound and (b) a specific phosphorus compound.Type: GrantFiled: January 5, 2007Date of Patent: September 11, 2007Assignee: JSR CorporationInventors: Noboru Oshima, Michitaka Kaizu, Satoshi Ebata, Takashi Imamura
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Patent number: 7264914Abstract: This invention provides novel fluorine containing polymers which comprise at least one fluorinated olefin, at least one polycyclic ethylenically unsaturated monomer with a fused 4-membered carbocyclic ring and, optionally, other components. The polymers are useful for photoimaging compositions and, in particular, photoresist compositions (positive-working and/or negative-working) for imaging in the production of semiconductor devices. The polymers are especially useful in photoresist compositions having high UV transparency (particularly at short wavelengths, e.g., 157 nm) which are useful as base resins in resists and potentially in many other applications.Type: GrantFiled: August 8, 2003Date of Patent: September 4, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Frank L Schadt, III, Viacheslav Alexandrovich Petrov, Bruce Edmund Smart, William Brown Farnham
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Patent number: 7250475Abstract: The present invention is directed to the preparation of photoresist polymers via living free radical polymerization techniques. Sterically bulky ester monomers are utilized as the polymerization components. Use of chain transfer agents is included in polymerization processing conditions. Cleavage of polymer terminal end groups that include a heteroatom are described.Type: GrantFiled: June 25, 2004Date of Patent: July 31, 2007Assignee: Symyx Technologies, Inc.Inventors: Didier Benoit, Adam Safir, Han-Ting Chang, Dominique Charmot, Kenji Okamoto, Isao Nishimura, Yong Wang
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Patent number: 7241847Abstract: A process for producing a cycloolefin addition polymer in which one or more cycloolefin monomers can be (co)polymerized by addition polymerization with a small palladium catalyst amount to produce a cycloolefin addition (co)polymer while attaining high catalytic activity. The process for cycloolefin addition polymer production is characterized by addition-polymerizing one or more cycloolefin monomers comprising a cycloolefin compound represented by a specific formula in the presence of a multi-component catalyst comprising (a) a palladium compound and (b) a specific phosphorus compound.Type: GrantFiled: August 4, 2004Date of Patent: July 10, 2007Assignee: JSR CorporationInventors: Noboru Oshima, Michitaka Kaizu, Satoshi Ebata, Takashi Imamura
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Patent number: 7238405Abstract: An insulating material comprising a cycloolefin polymer, specifically, an interlayer insulating material for a high-density assembly board having interlayer-connecting via holes at most 200 ?m in diameter, comprising a cycloolefin polymer containing at least 50 mol % of a repeating unit derived from a cycloolefin monomer; a dry film formed from a curable resin composition comprising a polymer having a number average molecular weight within a range of 1,000 to 1,000,000 as measured by gel permeation chromatography, and a hardener; and a resin-attached metal foil obtained by forming a film of a cycloolefin polymer on one side of a metal foil. Laminates, multi-layer laminates and build-up multi-layer laminates making use of these materials, and production processes thereof.Type: GrantFiled: February 4, 2004Date of Patent: July 3, 2007Assignee: Nippon Zeon Company, Ltd.Inventors: Yasuo Tsunogae, Yasuhiro Wakizaka, Junji Kodemura, Tohru Hosaka
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Patent number: 7232639Abstract: As a polymer exhibiting improved transparency which is suitable for a resist resin used in a chemical-amplification-type resist being applicable for photolithography using exposure light at 180 nm or shorter, this invention provides a polymer comprising a repeating unit resulting from polymerization of a monomer exhibiting a polymerization activity, wherein the monomer has a fluorine-containing acetal or ketal structure represented by general formula (1): wherein R represents an atomic group containing a carbon-carbon double bond exhibiting polymerization activity; at least one of R1 and R2 is fluorinated alkyl group or fluorinated aryl group having 1 to 20 carbon atoms; and R3 represents a radical selected from the group consisting of hydrogen atom, alkyl group, alkoxy-substituted alkyl group, fluorinated alkyl group, aryl group, fluorinated aryl group, aralkyl group and fluorinated aralkyl group having 1 to 20 carbon atoms.Type: GrantFiled: February 25, 2003Date of Patent: June 19, 2007Assignee: NEC CorporationInventors: Katsumi Maeda, Kaichiro Nakano
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Patent number: 7220810Abstract: A polymer film having a low dielectric constant is produced polymerizing a raw material gas containing a compound of the formula (1): wherein PCA represents a polycycloaliphatic hydrocarbon group, ALK represents a divalent aliphatic hydrocarbon group, m is 1 or 2, n is 0 or 1, and R1 and R2 represent independently each other an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryl group or an aryloxy group by a plasma polymerization method.Type: GrantFiled: June 16, 2005Date of Patent: May 22, 2007Assignees: Sumitomo Chemical Company, Limited, NEC Corporation, ASM Japan K.K.Inventors: Nobutaka Kunimi, Jun Kawahara, Akinori Nakano, Keizo Kinoshita
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Patent number: 7208260Abstract: The present invention discloses a cross-linking monomer represented by the following Chemical Formula 1, a process for preparing a photoresist polymer using the same, and said photoresist polymer: <Chemical Formula> wherein, R? and R? individually represent hydrogen or methyl; m represents a number of 1 to 10; and R is selected from the group consisting of straight or branched C1-10 alkyl, straight or branched C1-10 ester, straight or branched C1-10 ketone, straight or branched C1-10 carboxylic acid, straight or branched C1-10 acetal, straight or branched C1-10 alkyl including at least one hydroxyl group, straight or branched C1-10 ester including at least one hydroxyl group, straight or branched C1-10 ketone including at least one hydroxyl group, straight or branched C1-10 carboxylic acid including at least one hydroxyl group, and straight or branched C1-10 acetal including at least one hydroxyl group.Type: GrantFiled: February 22, 2002Date of Patent: April 24, 2007Assignee: Hynix Semiconductor Inc.Inventors: Jae Chang Jung, Keun Kyu Kong, Min Ho Jung, Geun Su Lee, Ki Ho Balk
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Patent number: 7202312Abstract: A method for preparing a cyclic olefin polymer is described. The method includes polymerizing cyclic olefin monomers or a cyclic olefin monomer with ethylene to prepare a cyclic olefin polymer solution; slowly adding a non-solvent drop wise to the cyclic olefin polymer solution to precipitate a cyclic olefin polymer; and filtering and drying the precipitated cyclic olefin polymer. In addition, the cyclic olefin polymer prepared using this method is described. According to the present invention, a spherical cyclic olefin polymer having a high bulk density can be easily separated from the cyclic olefin polymer solution by precipitation.Type: GrantFiled: January 27, 2005Date of Patent: April 10, 2007Assignee: LG Chem, Ltd.Inventors: Chul-Hwan Choi, Sung-Yeon Kim, Jung-Uk Choi
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Patent number: 7192682Abstract: There is provided a chemically-amplified resist composition having high transparency to light having a wavelength of 220 nanometers or smaller, excellent resistance to etching, and excellent adhesion to a substrate. The chemically-amplified resist composition is prepared through the use of at least one of a repeated structural unit having a bridged alicyclic ?-lactone structure defined in the general formula (III), a repeated structural unit having a bridged alicyclic ?-lactone structure defined in the general formula (IV), and a repeated structural unit having a bridged alicyclic ?-lactone structure defined in the general formula (V).Type: GrantFiled: June 27, 2003Date of Patent: March 20, 2007Assignee: NEC CorporationInventors: Katsumi Maeda, Kaichiro Nakano
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Patent number: 7173097Abstract: A composition curable by a metathesis reaction upon mixing its components and comprising an olefin-containing substrate, a metathesis catalyst, and a reaction control agent for slowing the progress of the metathesis reaction. The metathesis catalyst is a ruthenium or osmium carbene complex catalyst having high activity and good air stability. In one embodiment, the catalyst is free of phosphine ligands. The reaction control agent is an organic compound that contains carbon-carbon double and/or triple bonds and one or more Group 14 atoms and is present in an amount effective to slow the progress of the metathesis reaction. In one embodiment, the olefin-containing substrate may comprise one or more oligomers or polymers having a >20 wt. % linear siloxane (Si—O—Si) backbone tethered and/or end-capped with functional olefin groups, such as cycloalkenyl groups.Type: GrantFiled: July 15, 2004Date of Patent: February 6, 2007Assignee: Kerr CorporationInventor: Christos Angeletakis
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Patent number: 7169869Abstract: A resist composition comprising a polymer containing vinyl sulfonate units having fluorinated hydrophilic groups as a base resin has excellent transparency, substrate adhesion and developer penetrability as well as plasma etching resistance, and is suited for lithographic microprocessing.Type: GrantFiled: July 13, 2005Date of Patent: January 30, 2007Assignees: 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, Shinji Kishimura, Kazuhiko Maeda, Michitaka Ootani, Haruhiko Komoriya
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Patent number: 7160969Abstract: The invention relates to metathesis oligomers wherein one or more alkoxy ether groups are attached to the oligomer moiety. Also disclosed is a polymerizable composition comprising a catalytically effective amount of a penta- or hexavalent ruthenium or osmium carbene catalyst, the process for preparing the metathesis polymer by applying the reaction conditions of Ring Opening Metathesis Polymerization (=ROMP) to the polymerisable composition; and various technical applications of the metathesis oligomers as antifog agents.Type: GrantFiled: March 8, 2002Date of Patent: January 9, 2007Assignee: Ciba Specialty Chemicals Corp.Inventors: Piero Piccinelli, Manuel Vitali, Alessandro Zedda
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Patent number: 7157207Abstract: Provided is a polymer useful as a base resin of a resist material featuring a high resolution, patterns with less sidewall roughness, practically acceptable etching resistance, and a substantial margin allowed for heat treatment temperature after exposure. The polymer has a weight-average molecular weight of from 1,000 to 50,000 and comprises at least one repeating unit of formula (1) below, at least one repeating unit of formula (2) below and at least one repeating unit of formula (3) below. A resist material comprising the polymer is also provided.Type: GrantFiled: September 1, 2004Date of Patent: January 2, 2007Assignee: Shin-etsu Chemical Co., Ltd.Inventors: Kenji Funatsu, Tsunehiro Nishi, Shigehiro Nagura
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Patent number: 7157536Abstract: A composition that can be used as a component in auto clear coat and primer is disclosed. The composition comprises or is an alkoxylated amine having the formula of (A)[N(R1H)2]p including an isomer or mixture of isomers thereof. Also disclosed is a process, which comprises contacting an amine with an epoxide under a condition sufficient to produce an alkoxylated amine. Further disclosed is a composition that can be used as coating composition and primer, which comprises an alkoxylated amine and an organic polyisocyanate.Type: GrantFiled: January 19, 2004Date of Patent: January 2, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Gia Huynh-Ba, Patrick Henry Corcoran, Carl Brent Douglas, Christian Peter Lenges, John Stuart Coates
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Patent number: 7150957Abstract: Fluorinated vinyl ethers are provided having the structure of formula (I) the structure of formula (I) wherein at least one of X and Y is a fluorine atom, and L, R1, R2, R3, R4 are as defined herein. Also provided are copolymers prepared by radical polymerization of (I) and a second monomer that may not be fluorinated. The polymers are useful in lithographic photoresist compositions, particularly chemical amplification resists. In a preferred embodiment, the polymers are substantially transparent to deep ultraviolet (DUV) radiation, and are thus useful in DUV lithographic photoresist compositions. A method for using the composition to generate resist images on a substrate is also provided, i.e., in the manufacture of integrated circuits or the like.Type: GrantFiled: April 25, 2003Date of Patent: December 19, 2006Assignee: International Business Machines CorporationInventors: Richard A. DiPietro, Hiroshi Ito
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Patent number: 7148302Abstract: This invention is based upon the discovery that a catalyst system which is comprised of (a) palladium or a palladium compound and (b) a fluorinated alcohol is effective for polymerizing norbornene-functional monomers into polynorbornene-functional polymers. It has been further discovered that this catalyst system is more effective in polymerizing certain norbornene-functional monomers that are difficult to polymerize, such as norbornene ester monomers, than prior art catalyst systems. The activity of the catalyst systems of this invention can be further improved with respect to polymerizing some monomers by including a Lewis acid and/or a ligand, such as a phosphine or a carbene, in the system. In any case, the catalyst systems of this invention offer the advantage of being soluble in a wide variety of solvents, relatively inexpensive, and capable of polymerizing many norbornene-functional monomers that are difficult to polymerize with conventional catalyst systems.Type: GrantFiled: October 3, 2005Date of Patent: December 12, 2006Assignee: The Goodyear Tire & Rubber CompanyInventor: John-Henry Lipian
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Patent number: 7135533Abstract: This invention relates to olefin polymerization processes for polymerizing ethylene, higher alpha-olefin comonomer and dienes, especially vinyl norbornene, and especially process for producing amorphous or semi-crystalline polymers such as EPDM. The invention also relates to the novel polymers produced by such processes. The invention furthermore relates to articles of manufacture with an improved balance of toughness and curing properties.Type: GrantFiled: June 18, 2003Date of Patent: November 14, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventor: Perigaram S. Ravishankar
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Patent number: 7132215Abstract: Novel ester compounds having formula (1) wherein A1 is a polymerizable functional group having a double bond, A2 is furandiyl, tetrahydrofurandiyl or oxanorbornanediyl, R1 and R2 each are a monovalent hydrocarbon group, or R1 and R2 may bond together to form an aliphatic hydrocarbon ring with the carbon atom, and R3 is hydrogen or a monovalent hydrocarbon group which may contain a hetero atom are polymerizable into polymers. Resist compositions comprising the polymers are sensitive to high-energy radiation, have an improved sensitivity, resolution, and etching resistance, and lend themselves to micropatterning with electron beams or deep-UV rays.Type: GrantFiled: September 29, 2003Date of Patent: November 7, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Koji Hasegawa, Takeshi Kinsho, Takeru Watanabe
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Patent number: 7129014Abstract: The present invention provides a positive resist composition comprising a resin 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, an acid generator, and multifunctional epoxy compound, wherein the content of halogen atoms in the resin is 40% by weight or more, at least one of structural units constituting the resin is a structural unit having an alicyclic hydrocarbon skeleton, and the structural unit having an alicyclic hydrocarbon skeleton contains therein at least one group rendering the resin soluble in an alkali aqueous solution by the action of an acid, and at least one halogen atom.Type: GrantFiled: April 2, 2003Date of Patent: October 31, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Kouji Toishi, Yoshiko Miya, Yasunori Uetani
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Patent number: 7125642Abstract: A sulfonate compound having formula (1) is novel wherein R1 to R3 are H, F or C1-20 alkyl or fluoroalkyl, at least one of R1 to R3 contains F.Type: GrantFiled: February 9, 2004Date of Patent: October 24, 2006Assignees: 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, Shinji Kishimura, Kazuhiko Maeda, Haruhiko Komoriya, Satoru Miyazawa
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Patent number: 7122292Abstract: The present invention relates to novel first to fourth lactone compounds. The first lactone compound is represented by the formula (1), in the formula, X represents CH2, CH2CH2, O, S or NR1, and R1 represents hydrogen atom, a straight-chain, branched or cyclic alkyl group of a carbon number of 1–10. Hydrogen(s) of the alkyl group may partially or entirely be replaced with fluorine atom(s). Furthermore, a part of the alkyl group may contain an atomic group containing oxygen atom, sulfur atom, nitrogen atom, carbon-carbon double bond, carbonyl group, hydroxy group or carboxyl group.Type: GrantFiled: December 30, 2004Date of Patent: October 17, 2006Assignee: Central Glass Company, LimitedInventors: Shinichi Sumida, Haruhiko Komoriya, Katsutoshi Suzuki, Kazuhiko Maeda
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Patent number: 7119156Abstract: According to the present invention, a resist resin having in its structure a specific bridged-bond-containing aliphatic ring, and a resist composition comprising the same are provided. By using this resist composition, a resist pattern excellent in both transparency against short-wavelength light and dry-etching resistance can be formed by alkali development with high resolution.Type: GrantFiled: September 10, 2004Date of Patent: October 10, 2006Assignee: Kabushiki Kaisha ToshibaInventors: Takeshi Okino, Koji Asakawa, Naomi Shida, Toru Ushirogouchi, Satoshi Saito
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Patent number: 7115688Abstract: The invention provides a method of preparing nanoparticles having at least one polymer shell attached to them, each polymer shell having a selected property or properties. The method comprises attaching initiation monomers to the surfaces of the nanoparticles, contacting the nanoparticles having the initiation monomers attached to them with a transition metal ring-opening metathesis catalyst to activate the initiation monomers, and contacting the nanoparticles with one or more types of propagation monomers of the formula P—L—N under conditions effective so that the monomers are polymerized to form the one or more polymer shells. In the formula P—L—N, N is a cyclic olefin-containing group, P is a moiety which gives each polymer shell a selected property or properties, and L is a bond or linker. The invention also provides polymers formed by polymerizing the propagation monomers.Type: GrantFiled: November 30, 1999Date of Patent: October 3, 2006Assignee: Nanosphere, Inc.Inventors: Chad A. Mirkin, SonBinh T. Nguyen
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Patent number: 7101654Abstract: The disclosed invention relates to novel norbornene-type monomers containing pendent lactone or sultone groups. The invention also relates to norbornene-type polymers and copolymers comprising one or more repeating units represented by the formula: and containing pendent lactone or sultone groups. These polymers and copolymers are useful in making photoimagable materials. The photoimagable materials are particularly suitable for use in photoresist compositions useful in 193 and 157 nm photolithography.Type: GrantFiled: January 14, 2004Date of Patent: September 5, 2006Assignee: Promerus LLCInventors: Xiaoming Wu, Larry F. Rhodes, Lawrence Seger
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Patent number: 7098278Abstract: A polymerization catalyst for the polymerization and copolymerization of olefin monomers and the copolymerization of olefin monomers with other monomers selected from, for example, norbornenes and styrenes are disclosed. The polymerization catalysts disclosed contain a metal center selected from Ti, Zr, Hf, Ni and Pd with at least one chelating ligand.Type: GrantFiled: February 2, 2006Date of Patent: August 29, 2006Assignee: Rohm and Haas CompanyInventors: Brian L. Goodall, Robert Howard Grubbs, Andrew Willis Waltman
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Patent number: 7090968Abstract: The present invention includes polymers and photoresist compositions that comprise the polymers as a resin binder component. Photoresists of the invention include chemically-amplified positive-acting resists that can be effectively imaged at short wavelengths such as sub-200 nm, particularly 193 nm. Polymers of the invention contain in specified molar ratios both nitrile and photoacid labile groups that have an alicyclic moiety, particularly a bridged bicyclic or tricyclic group or other caged group. Polymers and resists of the invention can exhibit substantial resistance to plasma etchants.Type: GrantFiled: October 10, 2003Date of Patent: August 15, 2006Assignee: Shipley Company, L.L.C.Inventors: George G. Barclay, Zhibiao Mao, Robert J. Kavanagh
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Patent number: 7091290Abstract: The present invention relates to a method for preparing homo- and co-polymers having high molecular weights in high yields by polymerizing cyclic olefin compounds using a complex prepared by mixing a nickel salt compound, an organoaluminoxane compound, and at least one organic boron compound.Type: GrantFiled: November 23, 2004Date of Patent: August 15, 2006Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young Chan Jang, Hyun Kyung Sung
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Patent number: 7083893Abstract: Photoresist polymers and photoresist compositions are disclosed. A photoresist polymer represented by Formula 1 and a photoresist composition containing the same have excellent etching resistance, thermal resistance and adhesive property, and high affinity to an developing solution, thereby improving LER (line edge roughness). wherein X1, X2, R1, R2, m, n, a, b and c are as defined in the description.Type: GrantFiled: November 21, 2003Date of Patent: August 1, 2006Assignee: Hynix Semiconductor Inc.Inventor: Geun Su Lee
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Patent number: 7078147Abstract: A resist composition comprising a base polymer having sulfone or sulfonate units introduced therein is sensitive to high-energy radiation below 300 nm, is endowed with excellent adherence to substrates while maintaining transparency, and is suited for lithographic microprocessing.Type: GrantFiled: March 26, 2003Date of Patent: July 18, 2006Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., LtdInventors: Yuji Harada, Jun Hatakeyama, Masaru Sasago, Masayuki Endo, Shinji Kishimura
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Patent number: 7067231Abstract: A polymer comprising recurring units having a partial structure of formula (1) wherein R1 is a single bond or alkylene or fluoroalkylene, R2 and R3 are H or alkyl or fluoroalkyl, at least one of R2 and R3 contains at least one fluorine atom is used as a base resin to formulate a resist composition which has advantages including high transparency to radiation having a wavelength of up to 200 nm, substrate adhesion, developer affinity and dry etching resistanceType: GrantFiled: October 21, 2004Date of Patent: June 27, 2006Assignees: 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, Shinji Kishimura, Kazuhiko Maeda, Haruhiko Komoriya, Kazuhiro Yamanaka
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Patent number: 7060770Abstract: A composition curable by a metathesis reaction upon mixing its components and comprising an olefin-containing substrate, a metathesis catalyst, and a reaction control agent for slowing the progress of the metathesis reaction. The metathesis catalyst is a ruthenium or osmium curbene complex catalyst, such as one containing an alkylidene ligand with basicity higher than that of tricyclohexylphosphine (PCy3) and a neutral electron donor ligand with a basicity lower than that of PCy3, whereby the catalyst initiates the metathesis reaction of the composition upon mixing with the substrate. The reaction control agent is an organic compound that contains carbon-carbon double and/or triple bonds and one or more Group 14 atoms and is present in an amount effective to slow the progress of the metathesis reaction.Type: GrantFiled: May 6, 2003Date of Patent: June 13, 2006Assignee: Kerr CorporationInventor: Christos Angeletakis
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Patent number: 7060769Abstract: A method of controlled curing by a metathesis reaction upon mixing its components, the method including the step of mixing an olefin-containing substrate, a metathesis catalyst, and a reaction control agent. The metathesis catalyst is a ruthenium or osmium carbene complex catalyst, such as one containing an alkylidene ligand with basicity higher than that of tricyclohexylphosphine (PCy3) and a neutral electron donor ligand with a basicity lower than that of PCy3, whereby the catalyst initiates the metathesis reaction of the composition upon mixing with the substrate. The reaction control agent is effective to slow the progress of the metathesis reaction and prevent its completion in the absence of an elevated temperature. The control agent may be a hydrocarbon containing carbon-carbon double bonds and/or triple bonds, or maybe a modified hydrocarbon with one or more Group 14 or 15 atoms.Type: GrantFiled: May 6, 2003Date of Patent: June 13, 2006Assignee: Kerr CorporationInventor: Christos Angeletakis
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Patent number: 7056999Abstract: Disclosed herein are a ring-opened cycloolefin copolymer excellent in optical properties such as transparency, low in water (moisture) absorption property, high in affinity for other materials, good in post processing properties such as adhesive property and printability, and excellent in heat resistance and mechanical strength, a production process thereof, and an optical material. The ring-opened cycloolefin copolymer of the invention contains a structural unit (A) represented by any one of general formulae (1-1) to (1-3) and a structural unit (B) derived from a specific cycloolefin having an ester group in a proportion of 10:90 to 50:50 in terms of a molar ratio, wherein a monomer for obtaining the structural unit (A) is a tricyclomonoolefin compound containing an endo form in a proportion of at least 80 mol % and has a glass transition temperature of 120 to 250° C.Type: GrantFiled: June 19, 2003Date of Patent: June 6, 2006Assignee: JSR CorporationInventors: Kenzo Ohkita, Takashi Imamura, Noboru Oshima
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Patent number: 7041758Abstract: A process for polymerizing and copolymerizing cyclic olefins, such as, norbornene is disclosed. The disclosed process uses a catalyst complex that exhibit a high activity for the polymerization and co-polymerization of cyclic olefins and improved stability toward heat, oxygen and moisture.Type: GrantFiled: February 9, 2005Date of Patent: May 9, 2006Assignee: Rohm and Haas CompanyInventors: Brian L. Goodall, Lester Howard McIntosh, III
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Patent number: 7037995Abstract: Novel tertiary (meth)acrylate compounds having a lactone structure are polymerizable into polymers having improved transparency, especially at the exposure wavelength of an excimer laser and dry etching resistance. Resist compositions comprising the polymers are sensitive to high-energy radiation, have a high resolution, and lend themselves to micropatterning with electron beams or deep-UV rays.Type: GrantFiled: September 29, 2003Date of Patent: May 2, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Takeshi Kinsho, Koji Hasegawa
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Patent number: 7037993Abstract: A norbornene ring-opened polymer which in the molecule has repeating units represented by the formula (1): wherein R1 represents Q, R2 represents Q or C(?O)R5, R3 represents Q or C(?O)R6, and R4 represents Q or X—C(?O)R7 (wherein Q represents hydrogen, a C1-10 hydrocarbon group, etc.; R5, R6 and R7 each represents hydroxyl, C1-10 alkoxyl, etc., provided that R6 and R7 may be bonded to each other to constitute oxygen, NH, etc.; X represents methylene, etc., provided that when R2 is Q, then R3 is C(?O)R6 and R4 is X—C(?O)R7 and that when R4 is Q, then R2 is C(?O)R5, R3 is C(?O)R6, and the configuration of R2 and R3 is trans, and m is 0 or 1), the polymer having a weight-average molecular weight as determined by gel permeation chromatography of 1,000 to 1,000,000. Also provided is a hydrogenation product of the norbornene ring-opened polymer. The norbornene ring-opened polymer and the hydrogenation product are excellent in heat resistance, electrical properties, etc.Type: GrantFiled: April 7, 2003Date of Patent: May 2, 2006Assignee: Zeon CorporationInventors: Kazunori Taguchi, Seiji Okada, Yasuo Tsunogae
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Patent number: 7037974Abstract: A poly(?-olefin) copolymer obtained from the polymerization of at least one ?-olefin having from 2 to about 20 carbon atoms and at least one bulky olefin, the process comprising polymerizing the monomers in the presence of hydrogen and a catalytically effective amount of a catalyst comprising the product obtained by combining a metallocene procatalyst with a cocatalyst; lubricant compositions comprising such poly(?-olefin) copolymer; and a method for improving the viscosity index of a lubricant composition using such poly(?-olefin) copolymer.Type: GrantFiled: February 4, 2004Date of Patent: May 2, 2006Assignee: Uniroyal Chemical Company, Inc.Inventors: Anthony DiMaio, Thomas P. Matan
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Patent number: 7033728Abstract: The present invention relates to a photosensitive composition useful at wavelengths between 300 nm and 10 nm which comprises a polymer containing a substituted or unsubstituted higher adamantane.Type: GrantFiled: December 29, 2003Date of Patent: April 25, 2006Assignee: AZ Electronic Materials USA Corp.Inventor: Ralph R. Dammel
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Patent number: 7033729Abstract: Disclosed are a light absorbent agent polymer for organic anti-reflective coating which can prevent diffused reflection of lower film layer or substrate and reduce standing waves caused by variation of thickness of the photoresist itself, thereby, increasing uniformity of the photoresist pattern, in a process for forming ultra-fine patterns of photoresist for photolithography by using 193 nm ArF among processes for manufacturing semiconductor device, and its preparation method. Also, the present invention discloses an organic anti-reflective coating composition comprising the light absorbent agent polymer for the organic anti-reflective coating and a pattern formation process using the coating composition.Type: GrantFiled: October 12, 2004Date of Patent: April 25, 2006Assignee: Hynix Semiconductor Inc.Inventors: Jae-chang Jung, Keun Kyu Kong, Seok-kyun Kim
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Patent number: 7022458Abstract: Photoresist polymers and photoresist compositions are disclosed. A photoresist polymer represented by Formula 1 and a photoresist composition containing the same have excellent etching resistance, thermal resistance and adhesive property, and high affinity to an developing solution, thereby improving LER (line edge roughness). wherein X1, X2, X3, R1, R2, R3, R4, R5, m, n, o, a, b, c, d and e are as defined in the description.Type: GrantFiled: November 21, 2003Date of Patent: April 4, 2006Assignees: Hynix Semiconductor Inc., Dongjin Semichem Co., Ltd.Inventors: Geun Su Lee, Cheol Kyu Bok, Seung Chan Moon, Ki Soo Shin, Jae Hyun Kim, Jung Woo Kim, Sang Hyang Lee, Jae Hyun Kang
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Patent number: 7022790Abstract: A copolymer composition including a copolymer having repeat units of structural formula I: where X is selected from —CH2—, —CH2—CH2— and O; m is an integer from 0 to 5; and each occurrence of R1–R4 are independently selected from H; C1 to C25 linear, branched, and cyclic alkyl, aryl, aralkyl, alkaryl, alkenyl and alkynyl that can include one or more hetero atoms selected from O, N, and Si; a group that contains an epoxy functionality; —(CH2)nC(O)OR5; —(CH2)nC(O)OR6; —(CH2)nOR6; —(CH2)nOC(O)R6; —(CH2)nC(O)R6; —(CH2)nOC(O)OR6; and any combination of two of R1, R2, R3, and R4 linked together by a linking group. A portion of the repeat units having structural formula I contain at least one epoxy functional pendant group. The copolymer composition can be included with a material that photonically forms a catalyst in a photodefinable dielectric composition, which can be used to form a photodefinable layer on a substrate.Type: GrantFiled: June 19, 2003Date of Patent: April 4, 2006Assignee: Sumitomo Bakelite Company, Ltd.Inventors: Edmund Elce, Takashi Hirano, Jeffrey C. Krotine, Jr., Larry F. Rhodes, Brian L. Goodall, SaiKumar Jayaraman, W. Chris McDougall, Shenliang Sun
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Patent number: 7022457Abstract: The present invention pertains to photoimaging and the use of photoresists (positive-working and/or negative-working) for imaging in the production of semiconductor devices. The present invention also pertains to novel hydroxy ester-containing polymer compositions that are useful as base resins in resists and potentially in many other applications.Type: GrantFiled: September 24, 2003Date of Patent: April 4, 2006Assignee: E. I. du Pont de Nemours and CompanyInventors: William Brown Farnham, Andrew Edward Feiring, Frank Leonard Schadt, III, Weiming Qiu
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Patent number: 7015292Abstract: A silicon-containing olefin copolymer is provided which comprises (a) a constituent unit derived from —CH2—CH2— such as ethylene, (b) a constituent unit derived from —CH2—CHR— where R is a hydrocarbon group of 1 to 18 carbon atoms, and (c) a constituent unit containing a specific silicon-containing group. A silicon-containing olefin copolymer is also provided which is obtainable by co-polymerizing ethylene, an a-olefin of 3 to 20 carbon atoms and a specific silicon-containing ethylene monomer.Type: GrantFiled: December 26, 2002Date of Patent: March 21, 2006Assignee: Mitsui Chemicals, Inc.Inventors: Keiji Okada, Hidetatsu Murakami, Takashi Hakuta, Masaaki Kawasaki