Polyolefin Or Halogen Containing Patents (Class 430/907)
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Patent number: 6713228Abstract: Provided are alkenyl ether-based monomers having multi-ring structure, and photosensitive polymers and resist compositions obtained from the same. The photosensitive polymer includes a monomer unit represented by the following formula: wherein R4 and R5 are independently -H or -CH3, and R4 are independently -H, -OH or a alkyl group having 1-20 carbon atoms.Type: GrantFiled: April 24, 2002Date of Patent: March 30, 2004Assignee: Samsung Electronics Co., Ltd.Inventors: Hyun-Woo Kim, Sang-Gyun Woo, Sung-Ho Lee
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Patent number: 6709800Abstract: A presensitized plate for preparing a lithographic printing plate comprises a substrate provided thereon with a light-sensitive layer containing a fluoro-aliphatic group-containing copolymer prepared by copolymerizing at least (A) an addition polymerizable monomer having, on a side chain, a fluoro-aliphatic group in which hydrogen atoms are replaced with fluorine atoms and (B) a (meth)acrylate having an ester chain represented by a specific general formula. The use of the foregoing specific fluorine atom-containing polymer permits the formation of a light-sensitive layer having uniform surface condition without causing abnormality in the surface quality due to the foaming phenomenon observed during the production and also permits the production of a positive light-sensitive resin composition having excellent solubility and dispersibility in a developer.Type: GrantFiled: August 5, 2002Date of Patent: March 23, 2004Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuo Fujita, Shiro Tan
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Publication number: 20040053161Abstract: A chemical amplification type resist composition comprising:Type: ApplicationFiled: August 18, 2003Publication date: March 18, 2004Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Shinichi Kanna, Kazuyoshi Mizutani, Tomoya Sasaki
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Publication number: 20040053163Abstract: The present invention provides a presensitized plate useful for preparing a lithographic printing plate, which comprises a substrate provided thereon with a light-sensitive layer containing a fluoro-aliphatic group-containing copolymer prepared by copolymerizing at least (A) a fluoroalkyl(meth)acrylate represented by the general formula (I) and (B) a polyoxyalkylene group-containing ethylenic unsaturated monomer. By such a presensitized plate, a lithographic printing plate is provided with a light-sensitive layer whose uniformity and solubility or dispersibility in a developer are improved and which has an ability of forming high contrast images without entraining any reduction of the sensitivity.Type: ApplicationFiled: September 9, 2003Publication date: March 18, 2004Applicant: FUJI PHOTO FILM CO., LTD.Inventor: Kazuo Fujita
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Publication number: 20040048190Abstract: A positive photoresist composition comprising:Type: ApplicationFiled: August 19, 2003Publication date: March 11, 2004Applicant: FUJI PHOTO FILM CO., LTD.Inventor: Makoto Momota
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Publication number: 20040043321Abstract: A pattern formation material of this invention contains a base polymer including a first unit represented by Chemical Formula 1 and a second unit represented by Chemical Formula 2 and, and an acid generator: 1Type: ApplicationFiled: April 29, 2003Publication date: March 4, 2004Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Tsuyohiko Fujigaya
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Publication number: 20040038151Abstract: A photoresist element comprising a substrate; an etch resistant layer; and at least one photoresist layer prepared from a photoresist composition comprising a polymer selected from the group consisting of: (a) a fluorine-containing copolymer comprising a repeat unit derived from at least one ethylenically unsaturated compound characterized in that at least one ethylenically unsaturated compound is polycyclic; (b) a branched polymer containing protected acid groups, said polymer comprising one or more branch segment(s) chemically linked along a linear backbone segment; (c) fluoropolymers having at least one fluoroalcohol group having the structure: —C(Rf)(Rf′)OH, wherein Rf and Rf′ are the same or different fluoroalkyl groups of from 1 to about 10 carbon atoms or taken together are (CF2)n wherein n is 2 to 10; (d) amorphous vinyl homopolymers of perfluoro(2,2-dimethyl-1,3-dioxole) or CX2═CY2 where X═F or CF3 and Y═—H or amorphous vinyl copolymers of perfluoro(2,2-dimethylType: ApplicationFiled: April 9, 2003Publication date: February 26, 2004Inventors: Larry L Berger, Frank L Schadt
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Patent number: 6696217Abstract: A photosensitive monomer including a methylene butyrolactone derivative represented by the following formula: wherein R1 is a hydrogen atom or alkyl group, R2 is an acid-labile group, X is a hydrogen atom, or substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and Y is a substituted or unsubstitued alkyl group or alicyclic hydrocarbon group having 1 to 20 carbon atoms.Type: GrantFiled: February 20, 2002Date of Patent: February 24, 2004Assignee: Samsung Electronics Co., Ltd.Inventors: Kwang-sub Yoon, Sang-gyun Woo
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Patent number: 6689539Abstract: The present invention provides a photosensitive lithographic printing plate which displays superior ink receptivity and superior film strength of the photosensitive layer (image area). The photosensitive lithographic printing plate is produced by providing, on top of a support, a photosensitive composition comprising a fluororesin having a fluoro aliphatic group of 3 to 20 carbon atoms in which at least two of three terminal hydrogen atoms are substituted for fluorine atoms, and an ethylene based unsaturated group, as well as a negative photosensitive compound.Type: GrantFiled: April 20, 2001Date of Patent: February 10, 2004Assignee: Kodak Polychrome Graphics LLCInventors: Masamichi Kamiya, Koji Hayashi, Hirotaka Komine, Miyuki Makino
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Publication number: 20040023176Abstract: ABSTRACT A fluorinated polymer having a polydispersity index (Mw/Mn) of 1-1.20 can be prepared by subjecting an aromatic monomer having trifluoromethyl groups and acid labile groups to living anion polymerization. The fluorinated polymer is suitable for use in chemically amplified resist compositions having sensitivity to ultraviolet radiation.Type: ApplicationFiled: July 30, 2003Publication date: February 5, 2004Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Michitaka Ootani, Haruhiko Komoriya, Kazuhiko Maeda
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Publication number: 20040023150Abstract: Photoresists and associated processes for microlithography in the extreme, far, and near UV are disclosed. The photoresists in some embodiments comprise (a) a fluorine-containing copolymer comprising a repeat unit derived from at least one ethylenically unsaturated compound characterized in that at least one ethylenically unsaturated compound is polycyclic and at least one ethylenically unsaturated compound contains at least one fluorine atom covalently attached to an ethylenically unsaturated carbon atom; and (b) at least one photoactive component.Type: ApplicationFiled: March 27, 2002Publication date: February 5, 2004Inventors: Andrew E. Feiring, Frank L. Schadt
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Publication number: 20040023152Abstract: Photoresists and associated processes for microlithography in the extreme, far, and near UV are disclosed. The photoresists in some embodiments comprise (a) a fluorine-containing copolymer comprising a repeat unit derived from at least one ethylenically unsaturated compound characterized in that at least one ethylenically unsaturated compound is polycyclic and at least one ethylenically unsaturated compound contains at least one fluorine atom covalently attached to an ethylenically unsaturated carbon atom; and (b) at least one photoactive component.Type: ApplicationFiled: May 14, 2003Publication date: February 5, 2004Inventors: Andrew Edward Feiring, Jerald Feldman
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Patent number: 6686123Abstract: Photoresist monomers of following Formulas 1 and 2, photoresist polymers thereof, and photoresist compositions containing the same. The photoresist composition has excellent adhesiveness to a wafer, and is developable in aqueous tetramethylammonium hydroxide (TMAH) solution. In addition, the photoresist composition has low absorbance of light having the wavelength of 157 nm, and thus is suitable for a photolithography process using ultraviolet light sources such as VUV (157 nm) and EUV (13 nm) in fabricating a minute circuit for a high integration semiconductor device. wherein, R1, R2 and R3 are as defined in the specification of the invention.Type: GrantFiled: November 9, 2001Date of Patent: February 3, 2004Assignee: Hynix Semiconductor IncInventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung
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Patent number: 6673523Abstract: A resist film is formed by applying, on a semiconductor substrate, a resist material including at least one atom or group selected from the group consisting of a halogen atom, a cyano group, a nitro group, an alkoxy group, an amino group, an alkyl group, a trifluoromethyl group and a mercapto group. The resist film is irradiated with exposing light of a wavelength of a 1 nm through 180 nm band for pattern exposure, and the resist film is developed after the pattern exposure, so as to form a resist pattern.Type: GrantFiled: March 8, 2000Date of Patent: January 6, 2004Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Shinji Kishimura, Akiko Katsuyama, Masaru Sasago
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Publication number: 20030224287Abstract: A positive resist composition comprising: (A) a compound capable of generating an acid on exposure to active light rays or a radiation; (B) a resin which is insoluble or sparingly soluble in an alkali and becomes alkali-soluble by an action of an acid; and (D) an acyclic compound having at least three groups selected from a hydroxyl group and a substituted hydroxyl group.Type: ApplicationFiled: March 17, 2003Publication date: December 4, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventor: Toru Fujimori
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Publication number: 20030224283Abstract: A photoresist composition is provided that includes a polymer having at least one acrylate or methacrylate monomer having a formula 1Type: ApplicationFiled: May 31, 2002Publication date: December 4, 2003Applicant: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Brock, Richard A. DiPietro, Debra Fenzel-Alexander, Carl Larson, David R. Medeiros, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory M. Wallraff
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Publication number: 20030219680Abstract: A radiation-sensitive resin composition suitable as a chemically-amplified resist is provided. The composition comprised (A) a resin insoluble or scarcely soluble in alkali, but becoming alkali soluble by the action of an acid, and (B) a photoacid generator.Type: ApplicationFiled: May 2, 2003Publication date: November 27, 2003Inventors: Yukio Nishimura, Hiroyuki Ishii, Isao Nishimura, Eiichi Kobayashi
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Publication number: 20030219678Abstract: A resist composition comprising a base polymer having a fluorinated sulfonate or fluorinated sulfone introduced therein is sensitive to high-energy radiation, has excellent transparency, contrast and adherence, and is suited for lithographic microprocessing.Type: ApplicationFiled: March 25, 2003Publication date: November 27, 2003Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Michitaka Ootani, Haruhiko Komoriya
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Publication number: 20030215739Abstract: A resist composition comprising a base polymer having a fluorinated sulfonate or fluorinated sulfone introduced therein is sensitive to high-energy radiation below 300 nm, has excellent transparency, contrast and adherence, and is suited for lithographic microprocessing.Type: ApplicationFiled: March 25, 2003Publication date: November 20, 2003Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Michitaka Ootani, Haruhiko Komoriya
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Publication number: 20030211417Abstract: Nitrile/vinyl ether-containing polymers for photoresist compositions and microlithography methods employing the photoresist compositions are described. These photoresist compositions comprise 1) at least one ethylenically unsaturated compound comprised of a vinyl ether and 2) a nitrile-containing compound, e.g., acrylonitrile, which together impart high ultraviolet (UV) transparency and developability in basic media. In some embodiments, these photoresist compositions further comprise a fluoroalcohol group. The photoresist compositions of this invention have, high UV transparency, particularly at short wavelengths, e.g., 157 nm and 193 nm, which property makes them useful for lithography at these short wavelengths.Type: ApplicationFiled: October 16, 2002Publication date: November 13, 2003Inventors: Michael Fryd, Periyasamy Mookkan, Frank Leonard Schadt III
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Patent number: 6645693Abstract: A resist composition comprising a binder resin and a radiation-sensitive compound. The binder resin is an alkali-soluble resin or becomes alkali-soluble resin by the action of the radiation-sensitive compound after irradiation, and has a polymerization unit represented by the following formula (I): wherein, R1 represents a fluoroalkyl group having 1 to 12 carbon atoms and having at least one fluorine atom, and R2 represents hydrogen atom or an acyl group having 2 to 5 carbon atoms.Type: GrantFiled: June 27, 2001Date of Patent: November 11, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuhiko Hashimoto, Yoshiko Miya
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Publication number: 20030207202Abstract: The present invention provides a copolymer comprising repeating units derived from (A) at least one fluoroalkyl (meth) acrylate represented by the following general formula (I) or (II): 1Type: ApplicationFiled: January 29, 2003Publication date: November 6, 2003Applicant: Fuji Photo Film Co., Ltd.Inventors: Kazuo Fujita, Shiro Tan
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Publication number: 20030203308Abstract: A photosensitive resin composition of the present invention comprises (A) a resin having a repeating unit represented by formula (IA) and a repeating unit containing an acid decomposable group and copolymerizable with formula (IA), which is decomposed under the action of an acid to increase the solubility in an alkali developer, (B1) a compound capable of generating an aliphatic or aromatic sulfonic acid substituted by at least one fluorine atom upon irradiation with actinic rays or radiation, (B2) a compound capable of generating an aliphatic or aromatic sulfonic acid containing no fluorine atom, or an aliphatic or aromatic carboxylic acid upon irradiation with actinic rays or radiation, and (C) a solvent.Type: ApplicationFiled: March 5, 2003Publication date: October 30, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Kazuyoshi Mizutani, Shinichi Kanna
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Patent number: 6638689Abstract: Photoresist compositions, which can attain high-accuracy etching without causing separation and flexible printed wiring boards prepared with the photoresist compositions are disclosed. In order to etch a polyimide precursor layer on a conductive circuit, a photoresist composition comprising a photopolymerizable organic material (A), a water-soluble resin (B) and an amino-group-containing resin (C) is applied on the surface of the polyimide precursor layer to form a photoresist layer. Then, the photoresist layer is patterned by a photolithographic process. The polyimide precursor layer is etched and the pattern of the photoresist layer is transferred to the polyimide precursor layer. The amino-group-containing resin (C) in the photoresist layer is combined with an acid anhydride in the polyimide precursor layer to attain good adhesion and high-accuracy etching without causing separation of the photoresist layer.Type: GrantFiled: April 8, 1999Date of Patent: October 28, 2003Assignee: Sony Chemicals Corp.Inventors: Satoshi Takahashi, Akira Tsutsumi, Koichi Uno, Minoru Nagashima
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Publication number: 20030194645Abstract: A resist composition comprising a fluorinated polymer having carboxylate pendants and with a weight average molecular weight of 1,000-500,000 as a base resin is sensitive to high-energy radiation below 200 nm, has high transparency, resolution and plasma etching resistance, and is suited for lithographic microprocessing.Type: ApplicationFiled: April 4, 2003Publication date: October 16, 2003Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai
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Publication number: 20030194641Abstract: A positive resist composition comprising (A) a resin, which is decomposed by the action of an acid to increase solubility in an alkali developing solution, having a repeating unit represented by formula (Y) defined in the specification, (B) a compound capable of generating an acid upon irradiation of an actinic ray or radiation, and (C) a solvent.Type: ApplicationFiled: February 25, 2003Publication date: October 16, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Kazuyoshi Mizutani, Tomoya Sasaki, Shinichi Kanna
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Patent number: 6632582Abstract: A pattern formation material contains a base polymer including a siloxane compound represented by Chemical Formula 1: wherein R1 are the same or different compounds selected from the group consisting of an alkyl compound, an ester compound, an ether compound, a sulfone compound, a sulfonyl compound and an aromatic compound.Type: GrantFiled: April 19, 2001Date of Patent: October 14, 2003Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Shinji Kishimura, Masaru Sasago, Mitsuru Ueda
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Publication number: 20030186160Abstract: A copolymer is provided for use in a lithographic photoresist composition, particularly a chemical amplification photoresist. In a preferred embodiment, the copolymer is substantially transparent to deep ultraviolet radiation, i.e., radiation of a wavelength less than 250 nm, including 157 nm, 193 nm and 248 nm radiation, and has improved sensitivity and resolution. In one embodiment, the copolymer is comprised of an &agr;-cyano- or an &agr;-trifluoro-methacrylate monomer unit and a vinyl ether monomer unit. A lithographic photoresist composition containing the fluorinated copolymer is also provided, as is a process for using the composition to generate resist images on a substrate, i.e., in the manufacture of integrated circuits or the like.Type: ApplicationFiled: March 4, 2002Publication date: October 2, 2003Inventor: Hiroshi Ito
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Patent number: 6627382Abstract: A photosensitive polymer is provided which includes: (a) perfluoro-2,2-dimethy-1,3-dioxol derivatives having the following repeating unit: and (b) vinyl derivatives having the following repeating unit: wherein R1 is H, Cl, or F; each of R2 and R3 is H or F; R4 is H, F, CF3, OCF3, OCF2CF3, OCF2CF2CF3, CH2C(CF3)2OH, fluorinated alkyloxy group having an acid-labile group, n-perfluoroalkyl group having 1 to 8 carbon atoms, ORF, wherein RF is n-perfluoroalkyl group having 1 to 3 carbon atoms, or OQZ, wherein Q is perfluorinated alkylene group having 0 to 5 oxygen atoms, the sum of carbon atom and oxygen atom in the Q is 2 to 10, and Z is COOR, SO2F, CN, COF, or OCH3, wherein R is alkyl group having 1 to 4 carbon. A photoresist composition includes the photosensitive polymer and a photoacid generator(PAG).Type: GrantFiled: September 6, 2001Date of Patent: September 30, 2003Assignee: Samsung Electronics, Co., Ltd.Inventor: Hyun-woo Kim
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Patent number: 6627383Abstract: Photoresist monomers of following Formula 1, photoresist polymers thereof, and photoresist compositions using the same. The photoresist composition has excellent etching resistance, heat resistance and adhesiveness, and is developable in aqueous tetramethylammonium hydroxide (TMAH) solution. In addition, the photoresist composition has low light absorbance at the wavelength of 193 nm, 157 nm and 13 nm, and thus is suitable for a photolithography process using ultraviolet light sources such as VUV (157 nm) and EUV (13 nm) in fabricating a minute circuit for a high integration semiconductor device. wherein, R1, R2, R3, Y, W, m and n are as defined in the specification.Type: GrantFiled: October 9, 2001Date of Patent: September 30, 2003Assignee: Hynix Semiconductor IncInventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
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Publication number: 20030180665Abstract: This invention discloses compositions that can be polymerized/crosslinked imagewise upon exposure to ionization radiation such as x-ray, electron beam, ion beam, and gamma-ray. This invention also discloses methods of use for these compositions for microfabrication of ceramics, for stereolithography, and for x-ray, e-beam, and ion-beam lithography which can be used for photoresists.Type: ApplicationFiled: March 21, 2003Publication date: September 25, 2003Inventor: Ying Wang
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Patent number: 6623909Abstract: Polymers comprising recurring units of formula (1) are provided wherein R1 is a straight, branched or cyclic divalent C1-20 hydrocarbon group or a bridged cyclic hydrocarbon group, R is hydrogen atom or an acid labile group, 0≦m≦3, 0≦n≦3 and 0≦m+n≦6. Using the polymers, chemical amplification positive resist compositions featuring low absorption of F2 excimer laser light are obtained.Type: GrantFiled: June 1, 2001Date of Patent: September 23, 2003Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Toshiaki Takahashi, Toshinobu Ishihara, Jun Watanabe, Tohru Kubota, Yoshio Kawai
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Publication number: 20030171490Abstract: A polymer blend is provided for use in a lithographic photoresist composition, particularly a chemical amplification photoresist. In a preferred embodiment, the polymer blend is substantially transparent to deep ultraviolet radiation, i.e., radiation of a wavelength less than 250 nm, including wavelengths of 157 nm, 193 nm and 248 nm, and has improved sensitivity and resolution. Processes for preparing and using the polymer blend are also provided, as are lithographic photoresist compositions that contain the polymer blend.Type: ApplicationFiled: March 4, 2002Publication date: September 11, 2003Inventors: Gregory Breyta, Hiroshi Ito, Hoa D. Truong
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Publication number: 20030165776Abstract: A negative resist composition comprising (A) an alkali-soluble polymer, (B) a cross-linking agent forming cross-links between molecules of the alkali-soluble polymer (A) under the action of an acid and (C) a specified acid generator, which can satisfy all of performance requirements concerning sensitivity, resolution, pattern profile and line-edge roughness in the pattern formation by irradiation with electron beams or X-rays.Type: ApplicationFiled: December 30, 2002Publication date: September 4, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Shoichiro Yasunami, Kunihiko Kodama
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Publication number: 20030165773Abstract: A resist composition comprising a copolymer of an acrylic ester monomer containing fluorine at &agr;-position with a norbornene derivative containing oxygen or sulfur within the norbornene ring as a base resin is sensitive to high-nergy radiation below 200 nm, has excellent sensitivity, transparency and dry etching resistance, and is suited for lithographic microprocessing.Type: ApplicationFiled: December 26, 2002Publication date: September 4, 2003Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Michitaka Ootani, Haruhiko Komoriya
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Patent number: 6610456Abstract: Copolymers prepared by radical polymerization of a fluorine-containing aromatic monomer and an acrylate-based comonomer that may or 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, i.e., radiation of a wavelength less than 250 nm, including 157 nm and 248 nm 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: February 26, 2001Date of Patent: August 26, 2003Assignee: International Business Machines CorporationInventors: Robert David Allen, Phillip Joe Brock, Hiroshi Ito, Gregory Michael Wallraff
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Publication number: 20030157431Abstract: A radiation sensitive resin composition including a photo-acid generator and an aliphatic polymer having one or more electron withdrawing groups adjacent to or attached to a carbon atom bearing a protected hydroxyl group, wherein the protecting group is labile in the presence of in situ generated acid is described. The radiation sensitive resin composition can be used as a resist suitable for image transfer by plasma etching and enable one to obtain an etching image having high precision with high reproducibility with a high degree of resolution and selectivity.Type: ApplicationFiled: October 16, 2002Publication date: August 21, 2003Applicant: MASS INSTITUTE OF TECHNOLOGY (MIT)Inventor: Theodore H. Fedynyshyn
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Publication number: 20030152864Abstract: There is provided a novel fluorine-containing polymer having an acid-reactive group which has a high transparency against energy rays (radioactive rays) in a vacuum ultraviolet region (157 nm), and further there are provided a material for fluorine-containing base polymer prepared from the polymer and suitable for a photoresist and a chemically amplifying type resist composition obtained therefrom.Type: ApplicationFiled: October 3, 2002Publication date: August 14, 2003Applicant: Daikin Industries, Ltd.Inventors: Takayuki Araki, Meiten Koh, Yoshito Tanaka, Takuji Ishikawa, Hirokazu Aoyama, Tetsuo Shimizu
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Publication number: 20030148213Abstract: The following resist composition which is excellent particularly in transparency to light beams and dry etching properties and gives a resist pattern excellent in sensitivity, resolution, evenness, heat resistance, etc., as a chemical amplification type resist, is presented.Type: ApplicationFiled: December 19, 2002Publication date: August 7, 2003Applicant: ASAHI GLASS COMPANY LIMITEDInventors: Isamu Kaneko, Yoko Takebe, Shun-Ichi Kodama
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Patent number: 6599675Abstract: A polyimide having a repeating unit of the general formula (I) and a polyamic acid having a repeating unit of the formula (IV): (wherein, R1 and R2 represent H or a C1 to C20 alkyl group, and Z represents a condensed polycyclic aromatic group or an group of the following formulae: Herein, X represents —CO— or —C(═N2)—, Y represents a direct bond, —CH2—, —O—, —SO2—, —S—, —CO— or —C(═N2)—, and W represents a direct bond, —CH2—, —C(CH3)2—, —C(CF3)2—, —S—, —SO—, —SO2— or —O—, b, m and n are 0 or 1; r is a C1 to 4 alkyl group, halogen group or phenyl group; a is 0 or 1 to 3).Type: GrantFiled: December 19, 2001Date of Patent: July 29, 2003Assignee: Mitsui Chemicals, Inc.Inventors: Jun Kamada, Ken-ichi Goto, Takashi Kuroki, Shoji Tamai
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Patent number: 6596461Abstract: A compound of formula (I) wherein n is e.g. a number from 2 to 50; R5′ and R5″ are e.g. a group of formula (II); G1, G2, G3 and G4 are e.g. C1-C4akyl; R1 is e.g. hydrogen or C1-C4alkyl; R2 is e.g. methylene; R3′ is e.g. hydrogen and R3″ is e.g. hydrogen or C1-C4alkyl; R4 is e.g. C2-C8alkylene; and X is e.g. —N(R7)R8) with R7 and R8 being independently of one another hydrogen or C1-C8alkyl, is useful for stabilizing an organic material against degradation induced by light, heat or oxidation.Type: GrantFiled: May 22, 2001Date of Patent: July 22, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Dario Lazzari, Mirko Rossi, Graziano Zagnoni, Alessandro Zedda, Valerio Borzatta, Stephen Mark Andrews
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Patent number: 6596460Abstract: A copolymer useful in radiation sensitive compositions for lithographic printing plates comprises the units A, B, C and D, wherein A is present in an amount of 0.5 to 30 wt.-% and is of the formula wherein R is hydrogen, C1-C4 alkyl, —CH═COOH or B is present in an amount of 5 to 35 wt.-% and is of the formula C is present in an amount of 10 to 55 wt.Type: GrantFiled: December 29, 2000Date of Patent: July 22, 2003Assignee: Kodak Polychrome Graphics LLCInventors: Hans-Joachim Timpe, Ursula Müller
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Patent number: 6593058Abstract: Photoresists and associated processes for microlithography in the extreme, far, and near UV are disclosed. The photoresists in some embodiments comprise (a) a fluorine-containing copolymer comprising a repeat unit derived from at least one ethylenically unsaturated compound characterized in that at least one ethylenically unsaturated compound is polycyclic and at least one ethylenically unsaturated compound contains at least one fluorine atom covalently attached to an ethylenically unsaturated carbon atom; and (b) at least one photoactive component.Type: GrantFiled: March 23, 2001Date of Patent: July 15, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Andrew Edward Feiring, Jerald Feldman
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Publication number: 20030129527Abstract: The present invention relates to a novel negative working deep uv photoresist that is developable in an aqueous alkaline solution, and comprises a fluorinated polymer, photoactive compound and a crosslinking agent. The photoresist composition is particularly useful for patterning with exposure wavelengths of 193 nm and 157 nm.Type: ApplicationFiled: January 9, 2002Publication date: July 10, 2003Inventors: Takanori Kudo, Munirathna Padmanaban, Ralph R. Dammel, Medhat A. Touky
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Publication number: 20030124453Abstract: Acid-catalyzed positive resist compositions suitable for bilayer or multilayer lithographic applications are enabled by the use of a combination of (a) an acid-sensitive imaging polymer, (b) a radiation-sensitive acid generator, and (c) a non-polymeric silicon additive. The imaging polymer is preferably imageable with 193 nm or shorter wavelength imaging radiation. The resist compositions preferably contain at least about 5 wt. % silicon based on the weight of the imaging polymer. The compositions generally provide reduced line edge roughness compared to conventional silicon-containing resists.Type: ApplicationFiled: December 21, 2001Publication date: July 3, 2003Applicant: International Business Machines CorporationInventors: Wenjie Li, Pushkara Rao Varanasi, Ranee Kwong
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Publication number: 20030118935Abstract: An exposure method comprising a step of subjecting a resist layer to selective exposure to an ultraviolet light and forming a predetermined pattern in the resist layer, wherein a polymer material having introduced thereinto a cyclohexane group is used as a polymer material constituting the resist layer wherein all hydrogen atoms bonded to four continuously adjacent carbon atoms in the cyclohexane group are substituted by fluorine atoms. The use of a polymer material having a lowered absorption in the wavelength range of a vacuum ultraviolet (VUV) light in the resist material or resist layer enables a more improved ultra-fine processing than before.Type: ApplicationFiled: December 12, 2002Publication date: June 26, 2003Inventor: Nobuyuki Matsuzawa
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Patent number: 6582880Abstract: An acrylate resin containing fluorinated alkyl groups in ester side chains has high transmittance to VUV radiation. A resist composition using the resin as a base polymer is sensitive to high-energy radiation, has excellent sensitivity and resolution, and is suited for lithographic microprocessing.Type: GrantFiled: September 7, 2001Date of Patent: June 24, 2003Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co. Ltd., Central Glass Co., Ltd.Inventors: Yuji Harada, Jun Watanabe, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Michitaka Ootani, Satoru Miyazawa, Kentaro Tsutsumi, Kazuhiko Maeda
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Patent number: 6582882Abstract: The present invention includes an imageable element, comprising a substrate and a thermally imageable composition which includes a graft copolymer having hydrophobic and hydrophilic segments. Upon imagewise exposure to thermal energy, the graft copolymer produces exposed regions that are less soluble in a developer than the unexposed regions. Also included is a method of producing an imaged element which includes a graft copolymer according to the present invention.Type: GrantFiled: April 4, 2001Date of Patent: June 24, 2003Assignee: Kodak Polychrome Graphics LLCInventors: S. Peter Pappas, Shashikant Saraiya
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Publication number: 20030113659Abstract: In a resist composition comprising a base resin which is a high molecular weight structure free from an aromatic substituent group, a photoacid generator, and a solvent, the photoacid generator is a one capable of generating a perfluoroalkyl ether sulfonic acid. The resist composition has many advantages including excellent resolution, minimized size difference between isolated and densely packed patterns, and minimized line edge roughness.Type: ApplicationFiled: August 23, 2002Publication date: June 19, 2003Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Youichi Ohsawa, Tomohiro Kobayashi
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Patent number: 6579658Abstract: Polymers comprising recurring units of fluorinated maleic anhydride and/or fluorinated maleimide are novel. Using the polymers, resist compositions featuring low absorption of F2 excimer laser light are obtained.Type: GrantFiled: February 15, 2001Date of Patent: June 17, 2003Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Jun Watanabe, Yuji Harada