Binder Containing Patents (Class 430/905)
  • 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: 6969577
    Abstract: A positive resist composition comprising (A) a resin having a specific structure and capable of decomposing under action of an acid to increase solubility in an alkali developer, and (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation.
    Type: Grant
    Filed: March 4, 2004
    Date of Patent: November 29, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Yutaka Adegawa
  • Patent number: 6969579
    Abstract: Thermally imageable elements useful as lithographic printing plate precursors are disclosed. The elements may be either single layer or multilayer elements and comprise an alkali soluble co-polymer, or a mixture of alkali soluble co-polymers. The resulting printing plates have good resistance to pressroom chemicals.
    Type: Grant
    Filed: December 21, 2004
    Date of Patent: November 29, 2005
    Assignee: Eastman Kodak Company
    Inventors: Anthony Paul Kitson, Kevin Barry Ray
  • Patent number: 6969570
    Abstract: Thermally imageable elements useful as lithographic printing plate precursors are disclosed. The elements comprise a substrate, an underlayer over the substrate, and a top layer over the underlayer. The top layer comprises a co-polymer that comprises, in polymerized form, norbornene or a norbornene derivative. The resulting lithographic printing plates have good resistance to pressroom chemicals.
    Type: Grant
    Filed: October 26, 2004
    Date of Patent: November 29, 2005
    Assignee: Kodak Polychrome Graphics, LLC
    Inventor: Paul Kitson
  • Patent number: 6964840
    Abstract: A radiation-sensitive resin composition comprising an acid-labile group-containing resin and a photoacid generator is disclosed. The resin has a structure of the formula (1), wherein R1 represents a hydrogen atom, a monovalent acid-labile group, an alkyl group having 1-6 carbon atoms which does not have an acid-labile group, or an alkylcarbonyl group having 2-7 carbon atoms which does not have an acid-labile group, X1 represents a linear or branched fluorinated alkyl group having 1-4 carbon atoms, and R2 represents a hydrogen atom, a linear or branched alkyl group having 1-10 carbon atoms, or a linear or branched fluorinated alkyl group having 1-10 carbon atoms. The resin composition exhibits high transmittance of radiation, high sensitivity, resolution, and pattern shape, and is useful as a chemically amplified resist in producing semiconductors at a high yield.
    Type: Grant
    Filed: June 16, 2004
    Date of Patent: November 15, 2005
    Assignees: JSR Corporation, International Business Machines Corporation
    Inventors: Yukio Nishimura, Noboru Yamahara, Masafumi Yamamoto, Toru Kajita, Tsutomu Shimokawa, Hiroshi Ito
  • Patent number: 6964839
    Abstract: A photosensitive copolymer has a weight-average molecular weight of 3,000 to 100,000 and is represented by the following formula: wherein R1 is a hydrogen atom or methyl, R2 is an acid-labile tertiary alkyl group, and m/(m+n) is 0.5 to 0.8.
    Type: Grant
    Filed: November 20, 2000
    Date of Patent: November 15, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sang-jun Choi, Hyun-woo Kim, Sang-gyun Woo, Joo-tae Moon
  • Patent number: 6962768
    Abstract: Provided are a variety of monomers suitable of producing photosensitive polymers, that are in turn, useful in photoresist compositions, through radical (cationic) polymerization including at least one multi-ring alkenyl ethers and one ?-fluorinated acrylate. The resulting photoresist compositions exhibit both acceptable resistance to dry etching processing and light transmittance suitable for use with various light sources such as KrF excimer lasers, ArF excimer lasers or F2 excimer lasers, in a photolithography process to produce fine photoresist patterns. In addition to the multi-ring alkenyl ethers and ?-fluorinated acrylates, additional monomers comprising one or more cyclic aliphatic and heterocyclic compounds, both unsubstituted and substituted, in particular dihydropyrans, may be incorporated into the photosensitive polymers.
    Type: Grant
    Filed: March 12, 2004
    Date of Patent: November 8, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyun-Woo Kim, Sang-Gyun Woo
  • Patent number: 6962767
    Abstract: Acetal compounds in which a 5- or 6-membered ring acetal structure is connected to a norbornene structure through a linker represented by —(CH2)m— in which one hydrogen atom may be substituted with a hydroxyl or acetoxy group, and m is from 1 to 8 are novel. Using the acetal compounds as a monomer, polymers are obtained. A resist composition comprising the polymer as a base resin is sensitive to high-energy radiation and has excellent sensitivity, resolution, and etching resistance.
    Type: Grant
    Filed: December 10, 2002
    Date of Patent: November 8, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Takeshi Kinsho, Koji Hasegawa, Tsunehiro Nishi, Mutsuo Nakashima, Seiichiro Tachibana, Jun Hatakeyama
  • Patent number: 6953651
    Abstract: A chemical amplifying type positive resist composition having excellent sensitivity and resolution, manifesting no generation of scum is provided, which comprises a resin which has a polymerization unit derived from hydroxystyrene and a polymerization unit derived from 2-ethyl-2-adamantyl (meth)acrylate, and is insoluble or poorly soluble itself in an alkali, but becomes alkali-soluble after dissociation of the above-mentioned acid unstable group by the action of an acid; a radiation sensitive acid generating agent; and polypropylene glycol.
    Type: Grant
    Filed: January 17, 2002
    Date of Patent: October 11, 2005
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Katsuhiko Namba, Junji Nakanishi, Yasunori Uetani
  • Patent number: 6953649
    Abstract: The invention concerns a novel photosensitive composition for photoresist and a system comprising a substrate and a photoresist obtained from said novel composition. The photosensitive composition for photoresist comprises a copolymer with hydrophobic blocks whereof at least one block is an hydrophobic block capable of generating a hydrophilic block and comprising at its end a group selected among dithioesters, thioesters-thiones, dithiocarbamates and xanthates, and a photoactive compound capable of generating under the effect of a radiation an active species reacting with the hydrophobic block to generate the hydrophilic block.
    Type: Grant
    Filed: June 1, 2001
    Date of Patent: October 11, 2005
    Assignee: Rhodia Chimie
    Inventors: Evelyne Prat, Mathias Destarac
  • Patent number: 6951706
    Abstract: The present invention provides a sulfonate of the formula (I): wherein Q1, Q2, Q3, Q4 and Q5 each independently represent hydrogen, alkyl having 1 to 16 carbon atoms, alkoxy having 1 to 16 carbon atoms, halogen, aryl having 6 to 12 carbon atoms, aralkyl having 7 to 12 carbon atoms, cyano, sulfide, hydroxy, nitro or a group of the formula (I?) —COO—X—Cy1??(I?) wherein X represents alkylene and at least one —CH2— in the alkylene may be substituted by —O— or —S—, and Cy1 represents alicyclic hydrocarbon having 3 to 20 carbon atoms, and A+ represents a counter ion, with the proviso that at least one of Q1, Q2, Q3, Q4 and Q5 is the group of the formula (I?).
    Type: Grant
    Filed: August 25, 2003
    Date of Patent: October 4, 2005
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamaguchi, Yasunori Uetani, Hiroshi Moriuma
  • Patent number: 6951705
    Abstract: 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: Grant
    Filed: May 4, 2001
    Date of Patent: October 4, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Michael Fryd, Periyasamy Mookkan, Frank Leonard Schadt, III
  • Patent number: 6949323
    Abstract: Resist compositions comprising as the base resin a polymer using tert-amyloxystyrene as a reactive group which is decomposable under the action of an acid to increase solubility in alkali have advantages including a significantly enhanced contrast of alkali dissolution rate before and after exposure, a high sensitivity, and a high resolution in the baking temperature range of 100-110° C. which is unachievable with tert-butoxystyrene. The compositions are best suited as a chemically amplified resist material for micropatterning in the manufacture of VLSI.
    Type: Grant
    Filed: October 30, 2002
    Date of Patent: September 27, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takanobu Takeda, Osamu Watanabe, Kazunori Maeda, Hiroshi Miyakoshi
  • Patent number: 6946235
    Abstract: 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: Grant
    Filed: August 8, 2003
    Date of Patent: September 20, 2005
    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, Michitaka Ootani, Haruhiko Komoriya
  • Patent number: 6946233
    Abstract: Provided are a resist material having markedly high resolution and etching resistance of a practically usable level, and being useful for fine microfabrication; a patterning method using the resist material; and a polymer useful as a base resin for the resist material. More specifically, provided are a polymer having a weight-average molecular weight of 1,000 to 500,000, which comprises one or more repeating units selected from the group consisting of repeating units represented by formulae (1) to (3) below; and one or more repeating units of the formula (4) below; and a resist material containing the polymer.
    Type: Grant
    Filed: July 22, 2002
    Date of Patent: September 20, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Takeshi Kinsho
  • Patent number: 6939661
    Abstract: A composition for forming a radiation absorbing coating which comprises an organic solvent, a radiation absorbing polymer or a radiation absorbing material dissolved therein and a crosslinking agent having blocked isocyanate groups. Since the isocyanate groups of the crosslinking agent have been blocked, the composition containing the crosslinking agent has excellent storage stability. When the composition applied to a substrate and then baked, crosslinking proceeds to give an antireflective coating, which does not intermix with a resist layer to be formed thereon by coating and is free from diffusion of a photo-generated acid thereinto from the resist layer. As a result, a resist image free from footing or scum can be formed.
    Type: Grant
    Filed: August 30, 2002
    Date of Patent: September 6, 2005
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Wen-Bing Kang, Ken Kimura, Shoko Matsuo, Yoshinori Nishiwaki, Hatsuyuki Tanaka
  • Patent number: 6936400
    Abstract: A negative resist composition is provided which is less likely to swell in an alkali developing solution. An alkali-developable negative resist composition is disclosed comprising a compound (A) which generates an acid upon exposure to radiation, and a resin component (B) which becomes insoluble in alkali under the action of an acid, wherein the component (B) is a resin component containing: (b1) a unit which becomes insoluble in an alkali solution as a result of the formation of a lactone under the action of an acid generated from the component (A), and (b2) a unit having an alcoholic hydroxyl group.
    Type: Grant
    Filed: June 25, 2003
    Date of Patent: August 30, 2005
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Ryoichi Takasu, Miwa Miyairi, Jun Iwashita, Toshikazu Tachikawa
  • Patent number: 6936402
    Abstract: Disclosed herein is a novel norbornene, acrylate or methacrylate monomer as a photoresist monomer containing an oxepan-2-one group. Further disclosed are photoresist compositions comprising a polymer prepared from the monomer, methods for preparing the photoresist compositions, and methods for forming photoresist patterns using the photoresist compositions.
    Type: Grant
    Filed: February 24, 2004
    Date of Patent: August 30, 2005
    Assignee: Korea Advanced Institute Science & Technology
    Inventors: Jin-Baek Kim, Tae-Hwan Oh, Jae-Hak Choi, Jae-Jun Lee
  • Patent number: 6933097
    Abstract: A photosensitive composition for optical waveguides comprising of an organic oligomer, a polymerization initiator and a crosslinking agent, the organic oligomer being a silicone oligomer represented by the following formula (1), wherein X denotes hydrogen, deuterium, halogen, an alkyl group or an alkoxy group; m is an integer from 1 to 5; x and y represent the proportion of respective units, and neither x nor y is 0; and R1 denotes a methyl, ethyl, or isopropyl group; a production method thereof, and a polymer optical waveguide pattern formation method using the same.
    Type: Grant
    Filed: March 18, 2004
    Date of Patent: August 23, 2005
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Seiji Toyoda, Saburo Imamura, Satoru Tomaru, Takashi Kurihara, Koji Enbutsu, Shoichi Hayashida, Tohru Maruno
  • Patent number: 6933094
    Abstract: A chemically amplified radiation-sensitive resin composition comprising a specific copolymer and a photoacid generator, wherein the copolymer contains the following recurring unit (1) and/or the recurring unit (2), and the recurring unit (3-1), wherein R1 is a hydrogen or methyl, R2 is a C4-10 tertiary alkyl, R3and R4 are a hydrogen, C1-12 alkyl, C6-15 aromatic, C1-12 alkoxyl, or R3 and R4 may form, in combination and together with the nitrogen atom with which the R3 and R4 groups bond, a C3-15 cyclic structure, provided that R3 and R4 are not a hydrogen atom at the same time. The composition effectively responds to various radiations, exhibits excellent resolution and pattern configuration and minimal iso-dense bias, and can form fine patterns at a high precision and in a stable manner.
    Type: Grant
    Filed: September 18, 2001
    Date of Patent: August 23, 2005
    Assignee: JSR Corporation
    Inventors: Masaaki Miyaji, Tomoki Nagai, Yuji Yada, Jun Numata, Yukio Nishimura, Masafumi Yamamoto, Hiroyuki Ishii, Toru Kajita, Tsutomu Shimokawa
  • Patent number: 6929897
    Abstract: Polymers and co-polymers having monomeric units formed by the polymerization of monomers of the Structure I where R1 is a moiety containing an ethylenically unsaturated polymerizable group, R2 is a C1-C3 alkylene group, and R3 is a C1-10 linear or cyclic alkyl group, a C6-10 aromatic or substituted aromatic group, a C1-8 alkoxy methyl, or a C1-8 alkoxy ethyl group, are useful as binder resins for photosensitive compositions, and processes for photolithography in the production of semiconductor devices and materials.
    Type: Grant
    Filed: August 19, 2004
    Date of Patent: August 16, 2005
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Patrick Foster, Gregory Spaziano, Binod B De
  • Patent number: 6927011
    Abstract: A resist resin containing a monomer unit selected from the group comprising a monomer unit represented by Formula (II): wherein a substituent R3 represents an alkyl group, or a functional group comprising an acid-deprotectable protecting group, m representing the number of R3 is 0 (non-substitution), 1, 2 or more, R3 may be different from each other, provided that m is 2 or more, and n represents an integer of 0 to 4, has no rough spots on the surface after etching and so has good dry etching resistance, and therefore the resist resin is preferably used as a photo resist for DUV.
    Type: Grant
    Filed: February 9, 2001
    Date of Patent: August 9, 2005
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Tadayuki Fujiwara, Yukiya Wakisaka, Toru Tokimitsu, Naoshi Murata, Yoshihiro Kamon, Hikaru Momose
  • Patent number: 6924079
    Abstract: The present invention relates to a resist resin having an acid-decomposable group, which gives rise to decomposition of the acid-decomposable group to show an increased solubility to an aqueous alkali solution by the action of an acid, wherein the resist resin has, in the main chain, an alicyclic lactone structure represented by the following general formula (1). According to the present invention, a positive-type chemically amplified resist can be obtained which has high transparency to a far-ultraviolet light having a wavelength of about 220 nm or less, excellent etching resistance, and excellent adhesion to substrate; and a fine pattern required in production of semiconductor device can be formed. (wherein Z is an alicyclic hydrocarbon group having a lactone structure).
    Type: Grant
    Filed: July 2, 2001
    Date of Patent: August 2, 2005
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
  • Patent number: 6921622
    Abstract: Photoresist monomers of following Formula 1, photoresist polymers thereof, and photoresist compositions containing the same. The photoresist polymer includes a repeating unit comprising the photoresist monomer of Formula 1 as a comonomer and the photoresist composition containing the same have excellent etching resistance, heat resistance and adhesiveness to a wafer, and is developable in aqueous tetramethylammonium hydroxide (TMAH) solution.
    Type: Grant
    Filed: January 22, 2002
    Date of Patent: July 26, 2005
    Assignee: Hynix Semiconductor Inc.
    Inventors: Geun Su Lee, Jae Chang Jung, Ki Soo Shin
  • Patent number: 6921621
    Abstract: The present invention provides a resist composition comprising (A) polyhydroxystyrene in which at least a portion of hydrogen atoms of hydroxyl groups are substituted with an acid-dissociable dissolution inhibiting group, and the solubility in an alkali solution of the polyhydroxystyrene increasing when the acid-dissociable dissolution inhibiting group is eliminated by an action of an acid, and (B) a component capable of generating an acid by irradiation with radiation, wherein a retention rate of the acid-dissociable dissolution inhibiting group of the component (A) after a dissociation test using hydrochloric acid is 40% or less, and also provides a chemical amplification type positive resist composition which contains polyhydroxystyrene in which at least a portion of hydrogen atoms of hydroxyl groups are substituted with a lower alkoxy-alkyl group having a straight-chain or branched alkoxy group, and the solubility in an alkali solution of the polyhydroxystyrene increasing when the lower alkoxy-alkyl group
    Type: Grant
    Filed: June 28, 2002
    Date of Patent: July 26, 2005
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazuyuki Nitta, Takeyoshi Mimura, Satoshi Shimatani, Waki Okubo, Tatsuya Matsumi
  • Patent number: 6916592
    Abstract: 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: Grant
    Filed: March 25, 2003
    Date of Patent: July 12, 2005
    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, Michitaka Ootani, Haruhiko Komoriya
  • Patent number: 6916593
    Abstract: Although use of a nitrogen-containing compound as a basic compound component of a resist composition makes it possible to ease the T-top problem at an acid dissociation constant pKa falling within a range of 2 to 6, it is accompanied with the problem that the reaction, that is, acid diffusion upon use of a highly-reactive acid-labile group cannot be controlled. In order to overcome this problem, one or more basic compounds selected from those represented by the following formulas (I) to (III) and (1) to (4) are employed.
    Type: Grant
    Filed: July 9, 2003
    Date of Patent: July 12, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Youichi Ohsawa, Takeru Watanabe
  • Patent number: 6916590
    Abstract: 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. A resist composition which comprises a fluoropolymer (A) having repeating units represented by a structure formed by the cyclopolymerization of one molecule of a fluorinated diene and one molecule of a monoene, in which the monoene unit in each repeating unit has a blocked acid group capable of regenerating the acid group by the action of an acid, an acid-generating compound (B) which generates an acid upon irradiation with light, and an organic solvent (C).
    Type: Grant
    Filed: December 19, 2002
    Date of Patent: July 12, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Isamu Kaneko, Yoko Takebe, Shun-ichi Kodama
  • Patent number: 6916598
    Abstract: 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: Grant
    Filed: March 21, 2003
    Date of Patent: July 12, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Ying Wang
  • Patent number: 6916591
    Abstract: Photoacid generators are provided by O-arylsulfonyl-oxime compounds having formula (1) wherein R is H, F, Cl, NO2, alkyl or alkoxy, n is 0 or 1, m is 1 or 2, r is 0 to 4, r? is 0 to 5, k is 0 to 4, and G? and G? are S or —CH?CH—. Chemically amplified resist compositions comprising the photoacid generators have many advantages including improved resolution, improved focus latitude, minimized line width variation or shape degradation even on long-term PED, and improved pattern profile after development. Because of high resolution, the compositions are suited for microfabrication, especially by deep UV lithography.
    Type: Grant
    Filed: March 21, 2003
    Date of Patent: July 12, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Katsuhiro Kobayashi, Katsuya Takemura, Junji Tsuchiya, Kazunori Maeda
  • Patent number: 6911293
    Abstract: Disclosed is a photoresist composition comprising: a) at least one film forming resin selected from the group consisting of novolak resins, and polyhydroxystyrenes; b) at least one photoactive compound or photoacid generator; and c) a solvent composition comprising at least one solvent selected from the group consisting of acetals and ketals. Also disclosed is a photoresist composition comprising a polycarbonate resin and a solvent composition comprising at least one solvent selected from the group consisting of acetals and ketals. Also disclosed is a process for imaging a photoresist composition, comprising the steps of: a) coating a suitable substrate with any of the aforementioned photoresist compositions; b) baking the substrate to substantially remove the solvent; c) imagewise irradiating the photoresist film; and d) removing the imagewise exposed or, alternatively, the unexposed areas of the coated substrate with a suitable developer.
    Type: Grant
    Filed: April 11, 2002
    Date of Patent: June 28, 2005
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Stanley F. Wanat, Joseph E. Oberlander, Robert R. Plass, Douglas McKenzie
  • Patent number: 6908724
    Abstract: 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. The polymer has a number average molecular weight of from 1,000 to 1,000,000 and represented by the formula: —(M1)—(M2)—(A)—, wherein M1 is a structural unit having an acid-labile or acid-degradable functional group, M2 is a structural unit of fluorine-containing acryl ester, A is a structural unit derived from other copolymerizable monomer, the percent by mole ratio M1/M2 is 1 to 99/99 to 1 and the polymer comprises from 1 to 99% by mole of the structural unit M1, from 1 to 99% by mole of the structural unit M2 and from 0 to 98% by mole of the structural unit A1.
    Type: Grant
    Filed: October 3, 2002
    Date of Patent: June 21, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Takayuki Araki, Meiten Koh, Yoshito Tanaka, Takuji Ishikawa, Hirokazu Aoyama, Tetsuo Shimizu
  • Patent number: 6902875
    Abstract: A finely patterned silica type ceramic film suitable as an inter-layer dielectric is formed in a short time by applying, onto a substrate, a positive working radiation sensitive polysilazane composition comprising a modified poly(sil sesquiazane) having a number average molecular weight of 100 to 100,000 and containing a basic constituent unit represented by the general formula: —[SiR6(NR7)1.5]— and other constituent units represented by the general formula: —[SiR62NR7]— and/or —[SiR63(NR7)0.5]— (R6 and R7 independently represent a hydrogen atom, a C1-3 alkyl group or a substituted or unsubstituted phenyl group) in a ratio of 0.
    Type: Grant
    Filed: August 24, 2001
    Date of Patent: June 7, 2005
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Tatsuro Nagahara, Hideki Matsuo
  • Patent number: 6902860
    Abstract: The present invention includes a two-layer imageable element, including: a substrate, a top layer including a first thermally imageable composition including (a) a first thermally sensitive supramolecular polymer or (b) a thermally imageable composition free of the first thermally sensitive supramolecular polymer; and disposed between the substrate and the top layer, a bottom layer including a second thermally imageable composition, which includes a second thermally sensitive supramolecular polymer. The present invention also includes a method of producing the imaged element.
    Type: Grant
    Filed: December 28, 2001
    Date of Patent: June 7, 2005
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Yasuhiro Asawa, Yasuhiro Ishizuka, Eiji Hayakawa, S. Peter Pappas
  • Patent number: 6899994
    Abstract: The present invention relates to a polymerizable coating composition suitable for the manufacture of printing plates developable on-press. The coating composition comprises (i) a polymerizable compound and (ii) a polymeric binder comprising polyethylene oxide segments, wherein the polymeric binder is selected from the group consisting of at least one graft copolymer comprising a main chain polymer and polyethylene oxide side chains, a block copolymer having at least one polyethylene oxide block and at least one non-polyethylene oxide block, and a combination thereof. The invention is also directed to an imageable element comprising a substrate and the polymerizable coating composition.
    Type: Grant
    Filed: April 10, 2002
    Date of Patent: May 31, 2005
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Jianbing Huang, Heidi M. Munnelly, Shashikant Saraiya, Socrates Peter Pappas
  • Patent number: 6899989
    Abstract: A radiation-sensitive resin composition comprising (A) a photoacid generator such as 2,4,6-trimethylphenyldiphenylsulfonium 2,4-difluorobenzenesulfonate or 2,4,6-trimethylphenyldiphenylsulfonium 4-trifluoromethylbenzenesulfonate and (B) a resin having an acetal structure typified by a poly(p-hydroxystyrene) resin in which a part of hydrogen atoms of phenolic hydroxyl groups have been replaced by 1-ethoxyethyl groups, 1-ethoxyethyl groups and t-butoxycarbonyl groups, or 1-ethoxyethyl groups and t-butyl groups. The resin composition is sensitive to deep ultraviolet rays and charged particles such as electron beams, exhibits excellent resolution performance and pattern shape-forming capability, and suppresses a nano-edge roughness phenomenon to a minimal extent.
    Type: Grant
    Filed: November 16, 2001
    Date of Patent: May 31, 2005
    Assignee: JSR Corporation
    Inventors: Aki Suzuki, Makoto Murata, Hiromichi Hara, Eiichi Kobayashi
  • Patent number: 6897004
    Abstract: The intermediate layer material composition for a multilayer resist process in the present invention, which is soluble in an organic solvent, excellent in storage stability, and has no problem with regard to a footing shape, a pattern separation and a line edge roughness in patterning an upper resist, and a pattern formation process using the intermediate layer material composition, in which the intermediate layer material composition for a multilayer resist process, comprises a polymer (component A) containing a repeating unit having on a side chain thereof a specific structure containing a silicon atom-oxygen atom bond, and the pattern formation process using the same.
    Type: Grant
    Filed: September 2, 2003
    Date of Patent: May 24, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Kenichiro Sato
  • Patent number: 6897005
    Abstract: There are provided a photosensitive polymer having a copolymer of alkyl vinyl ether and a resist composition containing the same. The photosensitive polymer includes a copolymer of alkyl vinyl ether and maleic anhydride, represented by the following structure: wherein X is one of a linear alkyl vinyl ether and a cyclic alkyl vinyl ether, which are respectively represented by the structures wherein y is one of the integer values 1 through 4, R1 is one of a hydrogen atom and a methyl group, R2 is a C1 to C20 hydrocarbon, and R3 is one of a hydrogen atom, a C1 to C3 alkyl group and an alkoxy group.
    Type: Grant
    Filed: November 12, 2003
    Date of Patent: May 24, 2005
    Assignee: Samsung Electronics, Co., Ltd.
    Inventors: Sang-jun Choi, Hyun-woo Kim
  • Patent number: 6893794
    Abstract: A chemical amplification type positive resist composition comprising: (A) 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, and which contains a structural unit derived from p-hydroxystyrene and a structural unit represented by the formula (Ia) or (Ib) wherein R1 and R2 each independently represents hydrogen or methyl, and R3 to R5 each independently represents alkyl having 1 to 8 carbon atoms; and (B) radiation-sensitive acid generator comprising sulfonic acid ester of N-hydroxyimide compound; and onium salt is provided.
    Type: Grant
    Filed: July 21, 2003
    Date of Patent: May 17, 2005
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Akita, Satoshi Yamaguchi
  • Patent number: 6893793
    Abstract: The photosensitive polymer includes a first monomer which is norbornene ester having C1 to C12 aliphatic alcohol as a substituent, and a second monomer which is maleic anhydride. A chemically amplified photoresist composition, containing the photosensitive polymer, has an improved etching resistance and adhesion to underlying layer materials, and exhibits wettability to developing solutions.
    Type: Grant
    Filed: March 10, 2003
    Date of Patent: May 17, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Dong-won Jung, Sang-jun Choi, Si-hyeung Lee, Sook Lee
  • Patent number: 6890697
    Abstract: Disclosed is a novel positive-working chemical-amplification photoresist composition capable of giving an extremely finely patterned resist layer in the manufacturing process of semiconductor devices. The photoresist composition comprises: (A) 100 parts by weight of a copolymeric resin consisting of from 50 to 85% by moles of (a) hydroxyl group-containing styrene units, from 15 to 35% by moles of (b) styrene units and from 2 to 20% by moles of (c) acrylate or methacrylate ester units each having a solubility-reducing group capable of being eliminated in the presence of an acid; and (B) from 1 to 20 parts by weight of a radiation-sensitive acid-generating agent which is an onium salt containing a fluoroalkyl sulfonate ion having 3 to 10 carbon atoms as the anion such as bis(4-tert-butylphenyl) iodonium nonafluorobutane sulfonate.
    Type: Grant
    Filed: January 31, 2002
    Date of Patent: May 10, 2005
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Katsumi Oomori, Hiroto Yukawa, Ryusuke Uchida, Kazufumi Sato
  • Patent number: 6887646
    Abstract: The present invention discloses a chemically amplified resist composition comprising: a resin which becomes soluble in an aqueous alkali solution in the presence of an acid, a photo acid generator, and an amine derivative which shows, in water of 25° C., such a basicity as to form a conjugate acid and has a medium polarity. The amine derivative acts as a quencher. Therefore, the chemically amplified resist composition of the present invention enables formation of a very precise and fine resist pattern and can be suitably used particularly in a lithography using an ArF excimer laser beam.
    Type: Grant
    Filed: July 11, 2000
    Date of Patent: May 3, 2005
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Tadayuki Fujiwara, Yukiya Wakisaka, Masayuki Tooyama
  • Patent number: 6887644
    Abstract: A resist composition includes a polymer principal chain, a carboxyl group having a protective group and bonding to a side chain of the polymer main chain, and an additional acidic functional group having an acid-cleavable protective group and bonding to a side chain of the polymer main chain, wherein the carboxyl group has a lactone structure represented by a formula (wherein n is an integer of 1-4, and R represents any of a hydrogen atom, an alkyl group, an alkoxyl group and an alkoxycarbonyl group and connected to an arbitrary position of said lactone structure excluding a second position forming an ester bonding) as the protective group.
    Type: Grant
    Filed: January 29, 1998
    Date of Patent: May 3, 2005
    Assignee: Fujitsu Limited
    Inventors: Koji Nozaki, Ei Yano
  • Patent number: 6884566
    Abstract: A novel copolymer includes a repeating unit (B) derived from an unsaturated carboxylic anhydride, a repeating unit (C) represented by Formula (II), and a repeating unit (D) represented by Formula (III).
    Type: Grant
    Filed: October 16, 2003
    Date of Patent: April 26, 2005
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tsuyoshi Nakamura, Taeko Ikegawa, Atsushi Sawano, Kousuke Doi, Hidekatsu Kohara
  • Patent number: 6884563
    Abstract: A heat-sensitive composition can be used to make a heat-sensitive imaging material. The composition includes a water-soluble or water-dispersible binder and dispersed therein, a photothermal conversion material, and hybrid particles of a combustible nitro-resin and an addition polymer derived from one or more ethylenically unsaturated polymerizable monomers. The hybrid particles preferably have a core-shell structure with the combustible nitro-resin comprising the core and the addition polymer providing the shell. These imaging materials are particularly useful as “direct-write” thermally imageable elements useful to provide lithographic printing plates without ablation or the need for alkaline development.
    Type: Grant
    Filed: May 20, 2003
    Date of Patent: April 26, 2005
    Assignee: Eastman Kodak Company
    Inventors: Jeffrey W. Leon, Robert E. McCovick
  • Patent number: 6881531
    Abstract: 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: Grant
    Filed: December 12, 2002
    Date of Patent: April 19, 2005
    Assignee: Sony Corporation
    Inventor: Nobuyuki Matsuzawa
  • Patent number: 6878501
    Abstract: Polymers comprising recurring units of cycloolefin having fluorinated alkyl introduced therein are novel and have transparency and alkali solubility. Using the polymers, resist compositions featuring low absorption of F2 excimer laser light are obtained.
    Type: Grant
    Filed: April 26, 2001
    Date of Patent: April 12, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Jun Watanabe, Yuji Harada
  • Patent number: 6878504
    Abstract: A chemically-amplified resist composition is disclosed, which comprises a polymer of formula (I) below: wherein R1 is H, C1-C4 alkyl, or CF3; Q is C4-C12 cycloalkyl; R2 is H, C1-C4 alkyl, or CF3; R3 is C4-C12 branched or cyclic alkyl; and x+y+z equals to 1. The chemically-amplified resist compositions of the present invention not only can be applied maturely to general lithographic processes, especially to 193 nm lithographic process, but also have excellent photo-sensitivity, and can form a well-resolved pattern and profile.
    Type: Grant
    Filed: May 28, 2003
    Date of Patent: April 12, 2005
    Assignee: Everlight USA, Inc.
    Inventors: Chi-Sheng Chen, Chan-Chan Tsai, Bin Jian, Hsin-Ming Liao
  • Patent number: 6875552
    Abstract: The present invention provides a photoresist composition that reduces standing wave and side wall roughness. The 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. A method for making the photoresist composition is also provided.
    Type: Grant
    Filed: August 9, 2002
    Date of Patent: April 5, 2005
    Assignee: Micron Technology, Inc.
    Inventor: Yoshiki Hishiro
  • Patent number: 6872505
    Abstract: By using a branched long chained chain scission polymer as a photoresist for EUV and 157 nanometer applications, a relatively higher molecular weight polymer with good mechanical properties may be achieved. In addition, by using chain scission technology, line edge roughness and resolution may be improved at the same time.
    Type: Grant
    Filed: September 16, 2003
    Date of Patent: March 29, 2005
    Assignee: Intel Corporation
    Inventors: Heidi B. Cao, Robert P. Meagley