Polyolefin Or Halogen Containing Patents (Class 430/907)
  • Patent number: 7202011
    Abstract: Disclosed is a photosensitive polymer comprising pentafluoromethylvinyl ether derivative monomer having the formula: wherein R may be an alkoxy carbonyl, alkylsilane, a fluorine-substituted or unsubstituted C3–C20 alkyl carbonyl, a fluorine-substituted or unsubstituted C3–C20 cycloalkylcarbonyl or a fluorine-substituted or unsubstituted benzoyl substituent group. The photosensitive polymer is the polymerization product of the pentafluoromethylvinyl ether derivative monomer and at least one additional monomer selected from the group consisting of (meth)acrylic acid, (meth)acrylate, styrene, norbornene, tetrafluoroethylene and maleic anhydride monomers. The photosensitive polymer may be used in photoresist compositions for exposure light sources having a predominant wavelength of less than 157 nm.
    Type: Grant
    Filed: April 28, 2003
    Date of Patent: April 10, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Kwang-Sub Yoon, Sang-Gyun Woo, Ki-Yong Song, Sang-jun Choi
  • Patent number: 7202015
    Abstract: A positive photoresist composition containing: (A) a resin which contains at least one of a repeating unit represented by the formula (IA) defiend herein and a repeating unit represented by the formula (IB) defined herein, and is decomposed by an action of an acid and shows an increase in a solubility in an alkali developer; and (B) as compounds capable of generating an acid upon irradiation with one of an actinic ray and a radiation, at least two compounds selected from the compounds (B1), (B2), (B3) and (B4) as defiend herein.
    Type: Grant
    Filed: August 20, 2004
    Date of Patent: April 10, 2007
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinichi Kanna, Kazuyoshi Mizutani, Tomoya Sasaki
  • Patent number: 7192684
    Abstract: Polymerizable silicon-containing compounds of formula (1) wherein R1 is hydrogen, halogen or monovalent organic group are polymerized into polymers.
    Type: Grant
    Filed: September 29, 2003
    Date of Patent: March 20, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Takeru Watanabe, Koji Hasegawa
  • Patent number: 7189492
    Abstract: A photosensitive composition containing a compound capable of generating a specific acid having the plural number of sulfonic groups by irradiation with an actinic ray or a radiation and a pattern forming method using the same.
    Type: Grant
    Filed: September 10, 2004
    Date of Patent: March 13, 2007
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kunihiko Kodama, Kenji Wada, Kenichiro Satoh
  • Patent number: 7169530
    Abstract: The base polymer of a resist material contains a polymer compound including a first unit represented by a general formula of the following Chemical Formula 4 and a second unit represented by a general formula of the following Chemical Formula 5: wherein R1, R2 and R3 are the same or different and are a hydrogen atom, a fluorine atom, or 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 and R6 are the same or different and are 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; R7 is a methylene group, an oxygen atom, a sulfur atom or —SO2—; R8, R9, R10 and R11 are the same or different and are a hydrogen atom, a f
    Type: Grant
    Filed: October 1, 2004
    Date of Patent: January 30, 2007
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Hirokazu Imori, Toshiaki Fukuhara
  • Patent number: 7169531
    Abstract: A photoresist that is suitable for use in 157 nm photolithography includes a polymer based on fluorinated norbornene derivatives.
    Type: Grant
    Filed: October 28, 2004
    Date of Patent: January 30, 2007
    Assignees: Infineon Technologies, AG, AZ Electronic Materials USA Corp.
    Inventors: Christoph Hohle, Ralph Dammel, Michael Francis Houlihan
  • Patent number: 7169545
    Abstract: A resist exposure system and a method of forming a pattern on a resist are provided and include an exposure source, a photoresist composition, and a mask positioned therebetween. The resist composition comprises a first photoresist X and a second photoresist Y. The first photoresist X absorbs at a higher wavelength than the second photoresist Y. The second photoresist Y has a lower glass transitional temperature than the first photoresist X.
    Type: Grant
    Filed: August 19, 2004
    Date of Patent: January 30, 2007
    Assignee: Micron Technology, Inc.
    Inventor: Yoshiki Hishiro
  • Patent number: 7160666
    Abstract: 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: Grant
    Filed: March 5, 2003
    Date of Patent: January 9, 2007
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuyoshi Mizutani, Shinichi Kanna
  • Patent number: 7157206
    Abstract: A positive resist composition comprising (A) a resin containing at least one group that is decomposed by the action of an acid to generate an alkali-soluble group and (B) at least two compounds selected from (B1) a compound that generates an aliphatic or aromatic sulfonic acid substituted with at least one fluorine atom, (B2) a compound that generates an aliphatic or aromatic sulfonic acid that does not contain a fluorine atom, (B3) a compound that generates an aliphatic or aromatic carboxylic acid substituted with at least one fluorine atom and (B4) a compound that generates an aliphatic or aromatic carboxylic acid that does not contain a fluorine atom, as (B) a compound that generates an acid upon irradiation of an actinic ray or radiation, wherein the group that is decomposed by the action of an acid contained in the resin (A) includes a group represented by formula (Y) defined in the specification.
    Type: Grant
    Filed: July 23, 2004
    Date of Patent: January 2, 2007
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Haruki Inabe, Tomoya Sasaki
  • Patent number: 7147987
    Abstract: A positive resist composition comprising (A) a compound that generates an acid upon irradiation of an actinic ray or radiation and (B) a resin having a property of increasing solubility in an alkali developing solution by the action of an acid and including a repeating unit containing a partial structure represented by formula (X) defined in the specification and a repeating unit represented by formula (Y) defined in the specification.
    Type: Grant
    Filed: August 5, 2004
    Date of Patent: December 12, 2006
    Assignee: Fuji Photo Film Co. Ltd.
    Inventor: Kazuyoshi Mizutani
  • Patent number: 7138217
    Abstract: A positive resist composition comprises: (A) a resin capable of decomposing by the action of an acid to increase the solubility in an alkali developer; and (B) a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation, wherein the resin (A) contains a specified repeating unit.
    Type: Grant
    Filed: March 19, 2002
    Date of Patent: November 21, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Kazuyoshi Mizutani, Shinichi Kanna
  • Patent number: 7132216
    Abstract: An improved light attenuating compound for use in the production of microdevices is provided. Broadly, the light attenuating compound is non-aromatic and can be directly incorporated (either physically or chemically) into photolithographic compositions such as bottom anti-reflective coatings (BARC) and contact or via hole fill materials. The preferred non-aromatic compounds of the invention are conjugated aliphatic and alicyclic compounds which greatly enhance the plasma etch rate of the composition. Furthermore, the light attenuating compounds are useful for absorbing light at shorter wavelengths. In one embodiment, the inventive compounds can be polymerized so as to serve as both the polymer binder of the composition as well as the light absorbing constituent.
    Type: Grant
    Filed: October 20, 2003
    Date of Patent: November 7, 2006
    Assignee: Brewer Science Inc.
    Inventors: Xie Shao, Robert Cox, Shreeram V. Deshpande, Tony D. Flaim, Rama Puligadda
  • Patent number: 7129014
    Abstract: 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: Grant
    Filed: April 2, 2003
    Date of Patent: October 31, 2006
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kouji Toishi, Yoshiko Miya, Yasunori Uetani
  • Patent number: 7125640
    Abstract: A photoresist contains a polymer that has no silicon-containing groups. Consequently, no expulsion of silicon-containing compounds in gaseous form occurs on exposure to short-wave radiation. The polymer is obtained by terpolymerization of a first comonomer having a group cleavable under acid catalysis, a second comonomer having an anchor group, and a monounsaturated hydrocarbon, in which individual carbon atoms of the carbon skeleton may also be replaced by oxygen, as a third comonomer. The polymer has a low glass transition temperature, and the photoresist therefore has a good layer quality on film formation and good structurability.
    Type: Grant
    Filed: January 31, 2003
    Date of Patent: October 24, 2006
    Assignee: Infineon Technologies AG
    Inventors: Jörg Rottstegge, Michael Sebald
  • Patent number: 7125643
    Abstract: A polymer comprising recurring units of formula (1) and recurring units of formulae (2a) to (2d) wherein R1 is F or fluoroalkyl, R2 is a single bond or an alkylene or fluoroalkylene, R3 and R4 are H, F, alkyl or fluoroalkyl, at least one of R3 and R4 contains F, R5 is H or an acid labile group, R6 is an acid labile group, adhesive group, alkyl or fluoroalkyl, and “a” is 1 or 2 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 resistance.
    Type: Grant
    Filed: October 21, 2004
    Date of Patent: October 24, 2006
    Assignees: 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
  • Patent number: 7125943
    Abstract: A fluorine-containing compound represented by the formula 1, where R1 is a methyl group or trifluoromethyl group, each of R2 and R3 is independently a hydrogen atom or a group containing (a) a hydrocarbon group having a straight-chain, branched or ring form and having a carbon atom number of 1–25 or (b) an aromatic hydrocarbon group, each of the hydrogen group and the aromatic hydrocarbon group independently optionally containing at least one of a fluorine atom, an oxygen atom and a carbonyl bond, l is an integer of from 0 to 2, each of m and n is independently an integer of 1–5 to satisfy an expression of m+n?6, and when at least one of R1, R2 and R3 is present in a plural number, the at least one of R1, R2 and R3 may be identical with or different from each other.
    Type: Grant
    Filed: August 6, 2003
    Date of Patent: October 24, 2006
    Assignee: Central Glass Company, Limited
    Inventors: Shinichi Sumida, Haruhiko Komoriya, Kazuhiko Maeda
  • Patent number: 7125642
    Abstract: 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: Grant
    Filed: February 9, 2004
    Date of Patent: October 24, 2006
    Assignees: 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
  • Patent number: 7118847
    Abstract: Disclosed are spirocyclic olefin polymers, methods of preparing spirocyclic olefin polymers, photresist compositions including spirocyclic olefin resin binders and methods of forming relief images using such photoresist compositions.
    Type: Grant
    Filed: October 22, 2004
    Date of Patent: October 10, 2006
    Assignee: Shipley Company LLC
    Inventors: Charles R. Szmanda, George G. Barclay, Peter Trefonas, III, Wang Yueh
  • Patent number: 7118846
    Abstract: A positive resist composition comprises (A) a resin comprising specific repeating units and coming to have enhanced solubility in an alkaline developing solution by the action of an acid and (B) a compound generating an acid by the action of actinic rays or a radiation.
    Type: Grant
    Filed: March 10, 2004
    Date of Patent: October 10, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Tomoya Sasaki
  • Patent number: 7108953
    Abstract: The invention relates to a photoresist composition comprising a polymeric binder; a photoactive component; and at least one dissolution inhibitor comprising a paraffinic or cycloparaffinic compound containing at least one functional group having the structure —C(Rf)(Rf?)OR wherein Rf and Rf? are the same or different fluoroalkyl groups of from one or taken together are (CF2)a wherein a is an integer ranging from 2 to about 10 and R is a hydrogen atom or an acid labile protecting group. Typically, the dissolution inhibitor has an absorption coefficient of less than about 4.0 ?m at a wavelength of 157 nm.
    Type: Grant
    Filed: October 12, 2001
    Date of Patent: September 19, 2006
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Larry L. Berger, Jerald Feldman, Viacheslav Alexandrovich Petrov, Frank L. Schadt, III, Andrew E. Feiring, Fredrick Claus Zumsteg, Jr.
  • Patent number: 7108951
    Abstract: The photosensitive resin composition comprising: (A) a resin containing (A1) a repeating unit having at least two groups represented by the specific general formula; and (B) a compound capable of generating an acid by the action with one of an actinic ray and a radiation.
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: September 19, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tomoya Sasaki, Kazuyoshi Mizutani, Shinichi Kanna
  • Patent number: 7105267
    Abstract: 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: Grant
    Filed: August 23, 2002
    Date of Patent: September 12, 2006
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Youichi Ohsawa, Tomohiro Kobayashi
  • Patent number: 7101653
    Abstract: A laser-engravable flexographic printing element comprising an elastomeric, relief-forming, laser-engravable, thermally and/or photochemically crosslinkable layer comprising, as binder, at least 5% by weight of syndiotactic 1,2-polybutadiene having a content of 1,2-linked butadiene units of from 80 to 100%, a degree of crystallinity of from 5 to 30% and a mean molecular weight of from 20,000 to 300,000 g/mol on a flexible, dimensionally stable support. The elastomeric, relief-forming, laser-engravable layer preferably comprises: (a) from 50 to 99.9% by weight of one or more binders as component A consisting of (a1) from 5 to 100% by weight of syndiotactic 1,2-polybutadiene having a content of 1,2-linked butadiene units of from 80 to 100%, a degree of crystallinity of from 5 to 30% and a mean molecular weight of from 20,000 to 300,000 g/mol as component A1, and (a2) from 0 to 95% by weight of further binders as component A2, (b) from 0.
    Type: Grant
    Filed: April 15, 2002
    Date of Patent: September 5, 2006
    Assignee: XSYS Print Solutions Deutschland GmbH
    Inventors: Jürgen Kaczun, Jens Schadebrodt, Margit Hiller
  • Patent number: 7094515
    Abstract: A stimulus sensitive composition containing a compound capable of generating an acid or a radical on receipt of an external stimulus, the compound being represented by the following formula (I): wherein Y represents a group having a bridged cyclic structure; R1 and R2 each independently represent a hydrogen atom, an alkyl group or an aryl group; R1 and R2 may be taken together to form a ring; Y1 and Y2 each independently represent an alkyl group or an aryl group; Y1 and Y2 may be taken together to form a ring; and X? represents a non-nucleophilic anion.
    Type: Grant
    Filed: March 15, 2004
    Date of Patent: August 22, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kunihiko Kodama, Hyou Takahashi
  • Patent number: 7087356
    Abstract: Acid-catalyzed positive resist compositions which are imageable with 193 nm radiation and/or possibly other radiation and are developable to form resist structures of improved development characteristics and improved etch resistance are enabled by the use of resist compositions containing imaging polymer component comprising an acid-sensitive polymer having a monomeric unit with a pendant group containing a remote acid labile moiety.
    Type: Grant
    Filed: September 30, 2002
    Date of Patent: August 8, 2006
    Assignees: International Business Machines Corporation, JSR Corporation
    Inventors: Mahmoud H. Khojasteh, Kuang-Jung Chen, Pushkara Rao Varanasi, Yukio Nishimura, Eiichi Kobayashi
  • Patent number: 7083893
    Abstract: 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: Grant
    Filed: November 21, 2003
    Date of Patent: August 1, 2006
    Assignee: Hynix Semiconductor Inc.
    Inventor: Geun Su Lee
  • Patent number: 7081326
    Abstract: A negative photoresist composition and a method of patterning a substrate through use of the negative photoresist composition. The composition includes: a radiation sensitive acid generator; a multihydroxy-containing additive; and a resist polymer comprising a first repeating unit from a first monomer. The resist polymer may also comprise a second repeating unit from a second monomer, wherein the second monomer has an aqueous base soluble moiety. The multihydroxy-containing additive has the structure Q-(OH)m, where Q may include at least one alicycic group and m may be any integer between 2 and 6. The acid generator is adapted to generate an acid upon exposure to radiation. The resist polymer is adapted to chemically react with the additive in the presence of the acid to generate a product that is insoluble in a developer solution.
    Type: Grant
    Filed: March 11, 2004
    Date of Patent: July 25, 2006
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara R. Varanasi
  • Patent number: 7067231
    Abstract: 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 resistance
    Type: Grant
    Filed: October 21, 2004
    Date of Patent: June 27, 2006
    Assignees: 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
  • Patent number: 7063931
    Abstract: A positive photoresist composition comprises a radiations sensitive acid generator, and a polymer that may include a first repeating unit derived from a sulfonamide monomer including a fluorosulfonamide functionality, and a second repeating unit, which may include a pendant acid-labile moiety. The positive photoresist composition may also comprise at least one of a solvent, a quencher, and a surfactant. A patterned photoresist layer, made of the positive photoresist composition, may be formed on a substrate, the positive photoresist layer may be exposed to a pattern of imaging radiation, a portion of the positive photoresist layer that is exposed to the pattern of imaging radiation may be removed to reveal a correspondingly patterned substrate for subsequent processing in the manufacture of a semiconductor device.
    Type: Grant
    Filed: January 8, 2004
    Date of Patent: June 20, 2006
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara Rao Varanasi
  • Patent number: 7052820
    Abstract: A photoresist includes a polymer having a main chain composed of alternating silicon and oxygen atoms and a polymer chain segment which linked as a side chain to the main chain and whose chain is composed of carbon atoms. The chain composed of carbon atoms includes acid-labile groups, so that the photoresist according to the invention can be constructed as a chemically amplified photoresist.
    Type: Grant
    Filed: July 30, 2002
    Date of Patent: May 30, 2006
    Assignee: Infineon Technologies AG
    Inventors: Jörg Rottstegge, Eberhard Kühn, Waltraud Herbst, Christian Eschbaumer, Christoph Hohle, Michael Sebald
  • Patent number: 7045268
    Abstract: A photoresist composition having (A) at least two polymers 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-dimethyl-1,3-dioxole) and CX2?CY2; and (e) nitrile/fluoroalcohol-containing polymers prepared from substituted or unsubstituted vinyl ethers; and (B) at least
    Type: Grant
    Filed: November 21, 2001
    Date of Patent: May 16, 2006
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Larry L. Berger, Frank L. Schadt, III
  • Patent number: 7041428
    Abstract: A pattern formation material of this invention contains a base polymer including a unit represented by Chemical Formula 1 and, and an acid generator: Chemical Formula 1: wherein R1 is a hydrogen atom, a chlorine atom, a fluorine atom, an alkyl group or an alkyl group including a fluorine atom; and R2 is a protecting group released by an acid.
    Type: Grant
    Filed: September 12, 2002
    Date of Patent: May 9, 2006
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Tsuyohiko Fujigaya
  • Patent number: 7041426
    Abstract: A photoresist includes a polymer which has acid-cleavable groups in its main chain. The polymer can thus be cleaved by acid into short cleavage products which can be removed from the substrate through the use of a developer. The polymer is completely or partially fluorinated, and consequently has an improved transparency to light of short wavelengths.
    Type: Grant
    Filed: July 19, 2002
    Date of Patent: May 9, 2006
    Assignee: Infineon Technologies AG
    Inventors: Christian Eschbaumer, Christoph Hohle, Michael Sebald, Jörg Rottstegge
  • Patent number: 7037636
    Abstract: 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: Grant
    Filed: September 9, 2003
    Date of Patent: May 2, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Kazuo Fujita
  • Patent number: 7033727
    Abstract: A photosensitive composition of the present invention has excellent sensitivity and pattern profile, which comprises an acid generator having a specific structure.
    Type: Grant
    Filed: September 24, 2003
    Date of Patent: April 25, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Kunihiko Kodama
  • Patent number: 7033728
    Abstract: 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: Grant
    Filed: December 29, 2003
    Date of Patent: April 25, 2006
    Assignee: AZ Electronic Materials USA Corp.
    Inventor: Ralph R. Dammel
  • Patent number: 7022458
    Abstract: 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: Grant
    Filed: November 21, 2003
    Date of Patent: April 4, 2006
    Assignees: 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
  • Patent number: 7022457
    Abstract: 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: Grant
    Filed: September 24, 2003
    Date of Patent: April 4, 2006
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: William Brown Farnham, Andrew Edward Feiring, Frank Leonard Schadt, III, Weiming Qiu
  • Patent number: 7022456
    Abstract: A positive photoresist composition comprising: (A) an oxime sulfonate compound represented by the specific formula, (B) a resin comprising repeating units including a group represented by the specific formula and which increases the solubility in an alkaline developing solution by the action of an acid, and (C) a fluoroaliphatic-group-containing polymeric compound containing repeating units derived from a monomer represented by the specific formula.
    Type: Grant
    Filed: August 19, 2003
    Date of Patent: April 4, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Makoto Momota
  • Patent number: 7014983
    Abstract: Multilayer, thermally imageable elements useful as lithographic printing plate precursors are disclosed. The imageable elements comprise a substrate, an underlayer over the substrate, an underlayer over the substrate, and a top layer over the underlayer. The top layer contains a co-polymer that alkylene glycol side chains, polyalkylene glycol side chains, side chains that have silyl groups substituted with three alkoxy and/or phenoxy groups, and/or side chains that have alkyl ammonium side chains. The imageable elements have excellent resistance to press room chemicals.
    Type: Grant
    Filed: October 5, 2004
    Date of Patent: March 21, 2006
    Assignee: Eastman Kodak Company
    Inventors: Jayanti Patel, Ting Tao, Scott Beckley, John Kalamen
  • Patent number: 7014980
    Abstract: A photoresist composition is provided that includes a polymer having at least one acrylate or methacrylate monomer having a formula where R1 represents hydrogen (H), a linear or branched alkyl group of 1 to 20 carbons, or a semi- or perfluorinated linear or branched alkyl group of 1 to 20 carbons; and where R2 represents an unsubstituted aliphatic group or a substituted aliphatic group having zero or one trifluoromethyl (CF3) group attached to each carbon of the substituted aliphatic group, or a substituted or unsubstituted aromatic group; and where R3 represents hydrogen (H), methyl (CH3), trifluoromethyl (CF3), difluoromethyl(CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated aliphatic chain; and where R4 represents trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated substituted or unsubstituted aliphatic group. A method of patterning a substrate using the photoresist composition is also provided herein.
    Type: Grant
    Filed: August 12, 2004
    Date of Patent: March 21, 2006
    Assignee: International Business Machines Corporation
    Inventors: 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
  • Patent number: 7011923
    Abstract: A negative photoresist composition and a method of patterning a substrate through use of the negative photoresist composition. The negative photoresist composition comprises a radiation sensitive acid generator, a first polymer containing an alkoxymethyl amido group and a hydroxy-containing second polymer. The first and second polymers may also have a repeating unit having an aqueous base soluble moiety. The first and second polymers undergo acid catalyzed crosslinking upon exposure of the acid to radiation, producing a product that is insoluble in an aqueous alkaline developer solution.
    Type: Grant
    Filed: April 7, 2004
    Date of Patent: March 14, 2006
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara R. Varanasi
  • Patent number: 7008750
    Abstract: New methods are provided for synthesis of polysiloxanes (silsesquioxanes) and photoresists comprising same. Synthetic methods of the invention include use of a polymerization templating reagent that has multiple reactive nitrogen groups, particularly a diamine reagent.
    Type: Grant
    Filed: March 3, 2003
    Date of Patent: March 7, 2006
    Assignee: Shipley Company, L.L.C.
    Inventors: George G. Barclay, Subbareddy Kanagasabapathy, Matthew A. King
  • Patent number: 7005228
    Abstract: A ternary copolymer comprising units of ?-trifluoromethylacrylic carboxylate having acid labile groups substituted thereon, units of ?-trifluoromethylacrylic carboxylate having adhesive groups substituted thereon, and units of styrene having hexafluoroalcohol pendants is highly transparent to VUV radiation and resistant to plasma etching. A resist composition using the polymer as a base resin is sensitive to high-energy radiation below 200 nm, has excellent sensitivity, and is suited for lithographic microprocessing.
    Type: Grant
    Filed: June 25, 2002
    Date of Patent: February 28, 2006
    Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.
    Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Michitaka Ootani, Satoru Miyazawa, Kentaro Tsutsumi, Kazuhiko Maeda
  • Patent number: 7001707
    Abstract: A resist composition comprising a blend of a cyclic polymer having alcoholic groups as soluble groups and a polymer having carboxyl or hexafluoroalcohol groups whose hydrogen atoms are replaced by acid labile groups as a base resin forms a resist film which is improved in transparency, alkali dissolution contrast and plasma etching resistance.
    Type: Grant
    Filed: August 25, 2004
    Date of Patent: February 21, 2006
    Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.
    Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Haruhiko Komoriya, Kazuhiro Yamanaka
  • Patent number: 6994945
    Abstract: Novel silicon-containing polymers are obtained by copolymerizing a vinylsilane monomer with a compound having a low electron density unsaturated bond such as maleic anhydride, maleimide derivatives or tetrafluoroethylene. Using the polymers, chemical amplification positive resist compositions sensitive to high-energy radiation and having a high sensitivity and resolution at a wavelength of less than 300 nm and improved resistance to oxygen plasma etching are obtained.
    Type: Grant
    Filed: March 1, 2002
    Date of Patent: February 7, 2006
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takanobu Takeda, Jun Hatakeyama, Toshinobu Ishihara, Tohru Kubota, Yasufumi Kubota
  • Patent number: 6994946
    Abstract: Novel silicon-containing polymers are provided comprising recurring units having a POSS pendant and units which improve alkali solubility under the action of an acid. Resist compositions comprising the polymers are sensitive to high-energy radiation and have a high sensitivity and resolution at a wavelength of up to 300 nm and improved resistance to oxygen plasma etching.
    Type: Grant
    Filed: May 26, 2004
    Date of Patent: February 7, 2006
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takanobu Takeda
  • Patent number: 6991890
    Abstract: A negative photoresist composition and a method of patterning a substrate through use of the negative photoresist composition. The composition includes: a radiation sensitive acid generator; an additive; and a resist polymer derived from at least one first monomer including a hydroxy group. The first monomer may be acidic or approximately pH neutral. The resist polymer may be further derived from a second monomer having an aqueous base soluble moiety. The additive may include one or more alicyclic structures. The acid generator is adapted to generate an acid upon exposure to radiation. The resist polymer is adapted to chemically react with the additive in the presence of the acid to generate a non-crosslinking reaction product that is insoluble in an aqueous alkaline developer solution.
    Type: Grant
    Filed: February 6, 2004
    Date of Patent: January 31, 2006
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara R. Varanasi, Alyssandrea H. Hamad
  • Patent number: 6974658
    Abstract: Disclosed is a polymer compound for photoresist characterized in that the polymer compound is formed of a polymer compound having at least one skeleton represented by the following general formula (1), general formula (2A), general formula (2B) or general formula (2C):
    Type: Grant
    Filed: April 30, 2003
    Date of Patent: December 13, 2005
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Naomi Shida, Toru Ushirogouchi, Takuya Naito
  • Patent number: 6974657
    Abstract: A fluorine-containing polymer prepared from at least a spacer group selected from the group consisting of ethylene, alpha-olefins, 1,1?-disubstituted olefins, vinyl alcohols, vinyl ethers, and 1,3-dienes; and a norbornyl radical containing a functional group containing the structure: —C(Rf)(Rf?)Orb 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 an integer ranging from 2 to about 10 and Rb is a hydrogen atom or an acid- or base-labile protecting group; r is an integer ranging from 0-4. The fluorine-containing polymer has an absorption coefficient of less than 4.0 mm?1 at a wavelength of 157 nm. These polymers are useful in photoresist compositions for microlithography. They exhibit high transparency at this short wavelength and also possess other key properties, including good plasma etch resistance and adhesive properties.
    Type: Grant
    Filed: October 16, 2001
    Date of Patent: December 13, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Larry L. Berger, Michael Karl Crawford, Jerald Feldman, Lynda Kaye Johnson, Frank Leonard Schadt, III, Fredrick Claus Zumsteg, Jr.