Polyolefin Or Halogen Containing Patents (Class 430/907)
  • Patent number: 7511179
    Abstract: A fluorine-containing unsaturated cyclic compound represented by the formula (1)(a): wherein Z3 are the same or different and each is —Rf3-Z4, in which Z4 is at least one functional group selected from the group consisting of OH group, COOH group, a derivative of carboxylic acid group and a functional group protected by a protective group which can convert the functional group to OH group by reaction with an acid; Rf3 is a fluorine-containing alkylene group which has 1 to 30 carbon atoms and may have ether bond; n11 is an integer of from 1 to 4.
    Type: Grant
    Filed: May 17, 2006
    Date of Patent: March 31, 2009
    Assignee: Daikin Industries, Ltd.
    Inventors: Takayuki Araki, Takuji Ishikawa, Meiten Koh
  • Patent number: 7510822
    Abstract: A stimulation sensitive composition comprising: (A) a compound represented by the specific formula which is capable of generating an acid or a radical by stimulation from the external.
    Type: Grant
    Filed: April 9, 2003
    Date of Patent: March 31, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7510816
    Abstract: A resist composition is provided comprising a polysiloxane, a specific acid generator, a nitrogen-containing organic compound, and a solvent. The resist composition exerts high-resolution performance without the problem of a T-top profile and is suited for the bilayer resist process using ArF exposure.
    Type: Grant
    Filed: October 4, 2005
    Date of Patent: March 31, 2009
    Assignee: Shin-Estu Chemical Co., Ltd.
    Inventors: Katsuya Takemura, Kazumi Noda, Youichi Ohsawa
  • Patent number: 7507522
    Abstract: The present invention relates to novel unsaturated polycyclic compounds containing two fluoroalcohol substitutents. This invention also relates to homopolymers and copolymers derived from such unsaturated polycyclic compounds. The copolymers are useful for photoimaging compositions and, in particular, photoresist compositions (positive-working and/or negative-working) for imaging in the production of semiconductor devices. The polymers are especially useful in photoresist compositions having high UV transparency (particularly at short wavelengths, e.g., 157 nm) which are useful as base resins in resists and potentially in many other applications.
    Type: Grant
    Filed: May 17, 2005
    Date of Patent: March 24, 2009
    Assignee: E. I. DuPont de Nemours and Company
    Inventors: Michael Karl Crawford, Hoang Vi Tran, Frank Leonard Schadt, III, Fredrick Claus Zumsteg, Jr., Andrew Edward Feiring, Michael Fryd
  • Patent number: 7494764
    Abstract: A negative photosensitive resin composition comprising an alkali-soluble photosensitive resin (A) having acidic groups and having at least three ethylenic double bonds per molecule, an ink repellent (B) made of a polymer having polymerized units (b1) having a C20 or lower alkyl group in which at least one of its hydrogen atoms is substituted by a fluorine atom (provided that the alkyl group may contain etheric oxygen), and polymerized units (b2) having an ethylenic double bond, and a photopolymerization initiator (C), wherein the fluorine content in the ink repellent (B) is from 5 to 25 mass %, and the proportion of the ink repellent (B) is from 0.01 to 20 mass %, based on the total solid content of the negative photosensitive resin composition. The negative photosensitive resin composition of the present invention is excellent in adhesion to a substrate, ink repellency and durability thereof and further excellent in alkali solubility and developability.
    Type: Grant
    Filed: May 4, 2005
    Date of Patent: February 24, 2009
    Assignee: Asahi Glass Company, Limited
    Inventors: Hideyuki Takahashi, Kenji Ishizeki
  • Patent number: 7485408
    Abstract: Fluorine-containing silicon compounds having the general formula (1): wherein X1, X2, and X3 each are hydrogen, hydroxyl, halogen, a straight, branched or cyclic alkoxy group of 1 to 6 carbon atoms, or a monovalent organic group of 1 to 20 carbon atoms having a straight, branched, cyclic or polycyclic skeleton, Y is a divalent organic group, R1 and R2 are each independently hydrogen or a monovalent organic group of 1 to 20 carbon atoms having a straight, branched, cyclic or polycyclic skeleton, or R1 and R2 may bond together to form a ring with the carbon atom to which they are attached silicone resins obtained from the compounds of formula (1) has an appropriate acidity to enable formation of a finer pattern while minimizing the pattern collapse by swelling when used in a resist composition.
    Type: Grant
    Filed: March 5, 2007
    Date of Patent: February 3, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Mutsuo Nakashima, Koji Hasegawa, Takeru Watanabe
  • Patent number: 7485409
    Abstract: The present invention provides a planographic printing plate precursor including a support and a positive recording layer formed on the support and containing: (A) a polymer having a structural unit represented by the following general formula (1), (B) a photo-thermal converting agent, and (C) an amino compound having a methylol group or an alkoxymethyl group; and a positive recording layer whose solubility in an alkaline developer is improved by exposure to light or by heating. In general formula (1), R1 represents an alkyl group or a cyclic group, x represents 0 or 1, and A represents a bivalent bonding group. According to the invention, a positive planographic printing plate precursor for use with infrared lasers having excellent chemical resistance and wide image development latitude can be obtained.
    Type: Grant
    Filed: September 22, 2005
    Date of Patent: February 3, 2009
    Assignee: FujiFilm Corporation
    Inventor: Akira Nagashima
  • Patent number: 7476492
    Abstract: The present invention relates to a radiation sensitive photoresist composition. The composition comprises a polymer comprising at least two monomers. The first monomer has an acid cleavable tertiary ester group. The second monomer is an acidic monomer. The acid cleavable ester group of the polymer has a surprisingly low activation energy which results in improved resist images in lithographic processes.
    Type: Grant
    Filed: May 26, 2006
    Date of Patent: January 13, 2009
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 7470499
    Abstract: A noble alicyclic unsaturated compound represented by the general formula (1): wherein at least one of R1 and R2 is a fluorine atom or a fluorinated alkyl group; a polymer formed by the polymerization of a polymer precursor comprising the alicyclic compound. The polymer is useful, in the lithography using a light having a wavelength of 190 nm or less, as a chemically amplified resist which exhibits excellent transparency with respect to the light for use in exposure and also is excellent in the adhesion to a substrate and the resistance to dry etching.
    Type: Grant
    Filed: March 4, 2004
    Date of Patent: December 30, 2008
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Kaichiro Nakano
  • Patent number: 7449277
    Abstract: A polymer is obtained from (meth)acrylate having a bridged ring lactone group, (meth)acrylate having an acid-labile leaving group, and (meth)acrylate having a hydroxynaphthyl pendant. A positive resist composition comprising the polymer as a base resin, when exposed to high-energy radiation and developed, exhibits a high sensitivity, a high resolution, and a minimal line edge roughness due to controlled swell during development, and leaves minimal residues following development.
    Type: Grant
    Filed: September 20, 2006
    Date of Patent: November 11, 2008
    Assignee: Shin-Etsu Chemical C., Ltd
    Inventors: Jun Hatakeyama, Takeshi Nagata, Takanobu Takeda
  • Patent number: 7413843
    Abstract: A base polymer of a resist material includes a unit represented by a general formula of the following Chemical Formula 3: wherein R1, R2 and R3 are the same or different and are a hydrogen atom, a fluorine atom, a straight-chain alkyl group, a branched or cyclic alkyl group or a fluoridated alkyl group with a carbon number not less than 1 and not more than 20; R4 is a straight-chain alkylene group or a branched or cyclic alkylene group with a carbon number not less than 0 and not more than 20; and R5 and R6 are the same or different and are a hydrogen atom, a straight-chain alkyl group, a branched or cyclic alkyl group, 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.
    Type: Grant
    Filed: December 20, 2006
    Date of Patent: August 19, 2008
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Hirokazu Imori, Toshiaki Fukuhara
  • Patent number: 7410747
    Abstract: A positive resist composition satisfying high sensitivity, high resolution and good line edge roughness at the same time, and a pattern forming method using the composition, are provided, which is a positive resist composition comprising (A) a resin of which solubility in an alkali developer increases under the action of an acid, the resin containing a repeating unit having a specific styrene skeleton and a repeating unit having a specific ring structure, and (B) a compound of generating an acid upon irradiation with actinic rays or radiation; and a pattern forming method using the composition.
    Type: Grant
    Filed: September 26, 2005
    Date of Patent: August 12, 2008
    Assignee: FUJIFILM Corporation
    Inventor: Tomoya Sasaki
  • Patent number: 7402379
    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: February 23, 2006
    Date of Patent: July 22, 2008
    Assignee: Micron Technology, Inc.
    Inventor: Yoshiki Hishiro
  • Patent number: 7399815
    Abstract: The invention relates to a fluorine-containing allyl ether compound represented by the formula 1, wherein R represents an organic group containing at least one fluorine atom and an alicyclic structure. The invention further relates to a fluorine-containing copolymer containing a first unit derived from the fluorine-containing allyl ether represented by the formula 1; and a second unit derived from a vinyl monomer.
    Type: Grant
    Filed: July 25, 2006
    Date of Patent: July 15, 2008
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Kobayashi, Katsunori Kawamura, Kazuhiro Yamanaka, Haruhiko Komoriya, Kazuhiko Maeda
  • Patent number: 7390608
    Abstract: In a first aspect, silicon polymers are provided that have controlled ratio of silanol (Si—OH) moieties:Si atoms and/or a controlled amount of alkaline aqueous-solubilizing groups. Si-polymers of the invention are particularly useful as a photoresist resin component. In a further aspect, halogenated sulfonamide and thiol compounds and Si-containing polymers comprising such reacted monomers are provided.
    Type: Grant
    Filed: October 21, 2003
    Date of Patent: June 24, 2008
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: George G. Barclay, Subbareddy Kanagasabapathy
  • Patent number: 7390609
    Abstract: New polymers are provided that have non-carbon tetravalent species (Si, Ti, Ge, Zr, Sn) and photoimageable compositions that contain such polymers. Preferred polymers are organic, e.g. one or more polymer repeat units comprise carbon atom(s). Particularly preferred are polymers that comprise SiO2 or TiO2 repeat units and which can be highly useful as a resin component of resists imaged at short wavelengths such as sub-300 nm and sub-200 nm.
    Type: Grant
    Filed: March 3, 2004
    Date of Patent: June 24, 2008
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Anthony Zampini, Tao Zhang, Jaihyoung Lee
  • Patent number: 7385002
    Abstract: The present invention relates to a process for preparing a resin binder for toner, comprising the steps of (A) carrying out an addition polymerization reaction of addition polymerization resin monomers including styrene in the presence or absence of an organic solvent; and (B) mixing the resulting reaction mixture from the step (A) with water at a rate of 0.002 to 0.5 parts by weight based on 100 parts by weight of the addition polymerization resin monomers per minute at a temperature of 100° to 300° C. during and/or after the step (A), wherein the amount of water to be mixed in the step (B) is 0.1 to 50 parts by weight based on 100 parts by weight of the addition polymerization resin monomers. The resin binder for a toner obtained according to the present invention can be used, for instance, for developing electrostatic latent images formed in electrophotography, electrostatic recording method, electrostatic printing method, and the like, and a toner containing the resin binder.
    Type: Grant
    Filed: May 31, 2005
    Date of Patent: June 10, 2008
    Assignee: Kao Corporation
    Inventors: Eiji Shirai, Tetsuya Ueno
  • Patent number: 7368220
    Abstract: A positive resist composition, which comprises: (A) a resin of which solubility in an alkali developer increases under an action of an acid; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (C) a resin having at least one of a fluorine atom and a silicon atom; and (D) a solvent, wherein the resin (C) contains at least one of: (C1) a resin having at least one of a fluorine atom and a silicon atom and having an alicyclic structure; and (C2) a resin containing a repeating unit having at least one of a fluorine atom and a silicon atom in a side chain and a repeating unit having an unsubstituted alkyl group in a side chain; and a pattern forming method.
    Type: Grant
    Filed: December 11, 2006
    Date of Patent: May 6, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Hiromi Kanda, Shinichi Kanna
  • Patent number: 7358302
    Abstract: A composition for a light-scattering film contains fluorine-containing resin fine particles each including a copolymer of a first ethylenically unsaturated monomer containing fluorine with other ethylenically unsaturated monomer component, and having an average particle diameter of 0.8 to 5.0 ?m; and a transparent resin having a refractive index of 1.50 to 1.70. Where the other ethylenically unsaturated monomer component is formed of a second ethylenically unsaturated monomer containing no fluorine nor hydrophilic group, the copolymer contains 10 to 60% by weight of the first monomer, and 90 to 40% by weight of the second monomer. Where the other ethylenically unsaturated monomer component is formed of the second monomer and a third ethylenically unsaturated monomer containing a hydrophilic group, the copolymer contains 10 to 90% by weight of the first monomer, 89 to 5% by weight of the second monomer and 1 to 10% by weight of the third monomer.
    Type: Grant
    Filed: December 16, 2004
    Date of Patent: April 15, 2008
    Assignees: Toyo Ink Mfg. Co., Ltd., Toppan Printing Co., Ltd.
    Inventors: Yasuki Matsumoto, Kana Okazaki, Masayuki Kawashima, Hiromitsu Ito
  • Patent number: 7358027
    Abstract: 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 ?-cyano- or an ?-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: Grant
    Filed: March 4, 2002
    Date of Patent: April 15, 2008
    Assignee: International Business Machines Corporation
    Inventor: Hiroshi Ito
  • Patent number: 7335585
    Abstract: A method for manufacturing a semiconductor device which, on performing a via first Dual Damascene process, inhibits or prevents the formation of a void in a bottom anti-reflective coating filling a via hole. The method typically includes the steps of forming a bottom anti-reflective coating (BARC) in a via hole in an interlayer dielectric on a semiconductor substrate sufficiently to fill the via hole; disposing an acid diffusion material on the BARC; forming a cross-link layer between the BARC and the acid diffusion material; removing the remaining acid diffusion material; and etching the cross-link layer, the BARC and the interlayer dielectric to form a trench extending from an upper portion of the via hole.
    Type: Grant
    Filed: October 20, 2004
    Date of Patent: February 26, 2008
    Assignee: Dongbu Electronics Co., Ltd.
    Inventor: Yong Jun Choi
  • Patent number: 7326512
    Abstract: Provided are a polymer compound having high transparency for use in a photoresist composition for microfabrication of the next generation, a resist composition using the polymer compound as a base polymer, and a dissolution inhibitor agent composed of the polymer compound. To ensure etching resistance, an alicyclic group is introduced into a side chain portion. Hydrogen atoms on the ring of the alicyclic group are highly fluorinated to ensure transparency to light of 157 nanometer wavelength, represented by an adsorption coefficient equal to or less than 3.0 ?m?1. As the alicyclic group, a polycyclic group is preferably used. Hydrogen atoms are highly fluorinated by preferably substituting all hydrogen atoms on the ring by fluorine atoms, that is, forming a perfluoroalicyclic group. The resist composition is formed by using the polymer compound as a base polymer and further, the dissolution inhibitor agent is formed of the polymer compound.
    Type: Grant
    Filed: November 28, 2003
    Date of Patent: February 5, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Toshiyuki Ogata, Kotaro Endo, Hiromitsu Tsuji, Masaaki Yoshida, Hideo Hada, Ryoichi Takasu, Mitsuru Sato
  • Patent number: 7318985
    Abstract: A composition for photosensitive flexographic plates which is capable of forming a sheet having a smooth surface and excellent antiflowing properties and less apt to have trouble caused by sticking and which further has excellent thin-line reproducibility; a block copolymer composition for photosensitive flexographic plates which is suitable for use in the composition; and a flexographic plate obtained by exposing the composition to light. Also provided are: a block copolymer composition containing a three-branched aromatic vinyl/conjugated diene block copolymer obtained with a specific coupling agent; and a composition for photosensitive flexographic plates which comprises an ethylenic compound and a photopolymerization initiator.
    Type: Grant
    Filed: September 24, 2004
    Date of Patent: January 15, 2008
    Assignee: Zeon Corporation
    Inventors: Hidemi Tsubaki, Shinya Ikeda
  • Patent number: 7312016
    Abstract: A chemically amplified positive resist composition comprising a specific 2,4,6-triisopropylbenzenesulfonate compound as a photoacid generator, a polymer which changes its solubility in an alkaline developer under the action of acid, and a basic compound has a high sensitivity, a high contrast of dissolution of resist film, a high resolution, and good storage stability.
    Type: Grant
    Filed: October 19, 2006
    Date of Patent: December 25, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ryuji Koitabashi, Satoshi Watanabe, Youichi Ohsawa
  • Patent number: 7309560
    Abstract: There is provided a composition for forming anti-reflective coating for use in a lithography process with irradiation light from F2 excimer laser (wavelength 157 nm) which has a high effect of inhibiting reflected light and causes no intermixing with resist layers, and an anti-reflective coating prepared from the composition, and a method of controlling attenuation coefficient of the anti-reflective coating. Concretely, the composition is one containing a polymer compound containing halogen atom for forming anti-reflective coating for use in a lithographic process in manufacture of a semiconductor device. The polymer compound is one which halogen atom is introduced to a main chain thereof and/or a side chain bonded to the main chain. The attenuation coefficient can be controlled by changing the content of halogen atom in the solid content of the composition.
    Type: Grant
    Filed: February 14, 2003
    Date of Patent: December 18, 2007
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Rikimaru Sakamoto, Ken-ichi Mizusawa
  • Patent number: 7297466
    Abstract: An organic anti-reflective coating (ARC) is formed over a surface of a semiconductor substrate, and a resist layer including a photosensitive polymer is formed on the ARC. The photoresistive polymer contains a hydroxy group. The resist layer is then subjected to exposure and development to form a resist pattern. The resist pattern to then silylated to a given depth by exposing a surface of the resist pattern to a vapor phase organic silane mixture of a first organic silane compound having a functional group capable of reacting with the hydroxy group of the photoresistive polymer, and a second organic silane compound having two functional groups capable of reacting with the hydroxy group of the photoresistive polymer Then, the silylated resist pattern is thermally treated, and the organic ARC is an isotropically etched using the thermally treated resist pattern as an etching mask.
    Type: Grant
    Filed: February 28, 2003
    Date of Patent: November 20, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sung-ho Lee, Sang-gyun Woo, Yun-sook Chae, Ji-soo Kim
  • Patent number: 7291442
    Abstract: Image formation via photoinduced fluorescence changes in a polymeric medium with two-photon fluorescence readout of a multi-layer structure. Fluorophore-containing polymers, possessing one or more basic functional groups, underwent protonation in the presence of a photoinduced acid generator upon exposure to a broad-band UV light source or fast-pulsed red to near-IR laser irradiation. Solution studies demonstrated formation of monoprotonated and diprotonated species upon irradiation, each resulting in distinctly different absorption and fluorescence properties. The fluorescence of the original, neutral, fluorophore was reduced upon monoprotonation, leading to a concomitant increase in fluorescence at longer wavelengths due to the monoprotonated form, the basis for multichannel data readout.
    Type: Grant
    Filed: October 21, 2005
    Date of Patent: November 6, 2007
    Assignee: University of Central Florida Research Foundation, Inc.
    Inventor: Kevin D. Belfield
  • Patent number: 7288362
    Abstract: A topcoat material for applying on top of a photoresist material is disclosed. The topcoat material comprises at least one solvent and a polymer which has a dissolution rate of at least 3000 ?/second in aqueous alkaline developer. The polymer contains a hexafluoroalcohol monomer unit comprising one of the following two structures: wherein n is an integer. The topcoat material may be used in lithography processes, wherein the topcoat material is applied on a photoresist layer. The topcoat material is preferably insoluble in water, and is therefore particularly useful in immersion lithography techniques using water as the imaging medium.
    Type: Grant
    Filed: February 23, 2005
    Date of Patent: October 30, 2007
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Phillip Joe Brock, Dario Gil, William Dinan Hinsberg, Carl Eric Larson, Linda Karin Sundberg, Gregory Michael Wallraff
  • Patent number: 7288363
    Abstract: A chemically amplified positive resist composition comprising a specific 2,4,6-triisopropylbenzenesulfonate compound as a photoacid generator, a polymer which changes its solubility in an alkaline developer under the action of acid, and a basic compound has a high sensitivity, a high contrast of dissolution of resist film, a high resolution, and good storage stability.
    Type: Grant
    Filed: April 14, 2005
    Date of Patent: October 30, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ryuji Koitabashi, Satoshi Watanabe, Youichi Ohsawa
  • Patent number: 7276323
    Abstract: 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: Grant
    Filed: May 14, 2003
    Date of Patent: October 2, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Andrew Edward Feiring, Jerald Feldman
  • Patent number: 7267929
    Abstract: A negative photosensitive resin composition comprising an alkali-soluble photosensitive resin (A) having acidic groups and having at least three ethylenic double bonds per molecule, an ink repellent (B) made of a polymer having polymerized units (b1) having a C20 or lower alkyl group in which at least one of its hydrogen atoms is substituted by a fluorine atom (provided that the alkyl group may contain etheric oxygen), and polymerized units (b2) having an ethylenic double bond, and a photopolymerization initiator (C), wherein the fluorine content in the ink repellent (B) is from 5 to 25 mass %, and the proportion of the ink repellent (B) is from 0.01 to 20 mass %, based on the total solid content of the negative photosensitive resin composition. The negative photosensitive resin composition of the present invention is excellent in adhesion to a substrate, ink repellency and durability thereof and further excellent in alkali solubility and developability.
    Type: Grant
    Filed: September 6, 2006
    Date of Patent: September 11, 2007
    Assignee: Asahi Glass Company, Limited
    Inventors: Hideyuki Takahashi, Kenji Ishizeki
  • Patent number: 7264918
    Abstract: A resist composition for liquid immersion lithography process, which comprises: (A) a polymer comprising (a1) alkali-soluble constitutional units each comprising an alicyclic group having both (i) a fluorine atom or a fluoroalkyl group and (ii) an alcoholic hydroxyl group, wherein the polymer changes in alkali-solubility due to the action of acid; and (B) an acid generator which generates acid due to exposure to light, and a method for forming a resist pattern using the resist composition. By the resist composition or the method, an adverse effect of the immersion liquid can be avoided while achieving high resolution and high depth of focus.
    Type: Grant
    Filed: March 24, 2004
    Date of Patent: September 4, 2007
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kotaro Endo, Masaaki Yoshida, Taku Hirayama, Hiromitsu Tsuji, Toshiyuki Ogata, Mitsuru Sato
  • Patent number: 7264914
    Abstract: This invention provides novel fluorine containing polymers which comprise at least one fluorinated olefin, at least one polycyclic ethylenically unsaturated monomer with a fused 4-membered carbocyclic ring and, optionally, other components. The polymers are useful for photoimaging compositions and, in particular, photoresist compositions (positive-working and/or negative-working) for imaging in the production of semiconductor devices. The polymers are especially useful in photoresist compositions having high UV transparency (particularly at short wavelengths, e.g., 157 nm) which are useful as base resins in resists and potentially in many other applications.
    Type: Grant
    Filed: August 8, 2003
    Date of Patent: September 4, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Andrew E. Feiring, Frank L Schadt, III, Viacheslav Alexandrovich Petrov, Bruce Edmund Smart, William Brown Farnham
  • Patent number: 7261993
    Abstract: Positive photoresists and associated processes for microlithography in the ultraviolet (UV) and violet are disclosed. The photoresists comprise (a) a branched polymer containing protected acid groups and (b) at least one photoacid generator. The photoresists have high transparency throughout the UV, good development properties, high plasma etch resistance and other desirable properties, and are useful for microlithography in the near, far, and extreme UV, particularly at wavelengths less than or equal to 365 nm.
    Type: Grant
    Filed: October 21, 2004
    Date of Patent: August 28, 2007
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Frank Leonard Schadt, III, Michael Fryd, Mookkan Periyasamy
  • Patent number: 7255971
    Abstract: A positive resist composition comprising the components of: (A) a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation; (B) a resin that is insoluble or slightly soluble in alkalis, but becomes alkali-soluble under an action of an acid; (C) a basic compound; and (D) a compound comprising at least three hydroxyl groups or at least three substituted hydroxyl groups, and comprising at least one cyclic structure.
    Type: Grant
    Filed: September 16, 2002
    Date of Patent: August 14, 2007
    Assignee: Fujifilm Corporation
    Inventors: Toru Fujimori, Yasumasa Kawabe
  • Patent number: 7255973
    Abstract: A polymer comprising units derived from an exo-form ester and units derived from an ester having two hexafluoroisopropanol groups is used as a base resin to formulate a positive resist composition which, when exposed and developed by photolithography, is minimized in line edge roughness by swelling during development and residue after development, and improved in adhesion.
    Type: Grant
    Filed: April 8, 2005
    Date of Patent: August 14, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Tatsushi Kaneko
  • Patent number: 7244545
    Abstract: The present invention provides a fluorinated compound having functional groups in a high concentration so that adequate characteristics of the functional groups can be obtained and having high transparency in a wide wavelength region, a fluoropolymer, and a process for its production. The present invention provides a fluorinated diene represented by the following formula (1): CF2?CFCH2CH(C(R1)(R2)(OH))CH2CH?CH2??(1) wherein each of R1 and R2 which are independent of each other, is a fluorine atom or a fluoroalkyl group having at most 5 carbon atoms.
    Type: Grant
    Filed: April 27, 2006
    Date of Patent: July 17, 2007
    Assignee: Asahi Glass Company, Limited
    Inventors: Yoko Takebe, Osamu Yokokoji
  • Patent number: 7241553
    Abstract: A chemically amplified resist composition using an alternating copolymer of ?-trifluoroacrylic acid with norbornene as a base polymer lends itself to ArF laser lithographic micropatterning and is improved in transparency, plasma etching resistance, and line edge roughness.
    Type: Grant
    Filed: January 27, 2005
    Date of Patent: July 10, 2007
    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: 7235344
    Abstract: A composition including a first moiety; and a different second moiety capable of harvesting energy from an external source, wherein the second moiety is positioned such that energy harvested at the second moiety may be transferred to the first moiety. An article of manufacture including a film including a first moiety and a different second moiety capable of harvesting energy from an external source, wherein the second moiety is positioned such that collectively the first and second moieties have an electron capture cross-section greater than the electron capture cross-section of the first moiety alone. A method including forming a film on a substrate including a first moiety and a different second moiety; exposing the film to photonic or charged particle radiation; and patterning the film.
    Type: Grant
    Filed: June 30, 2004
    Date of Patent: June 26, 2007
    Assignee: Intel Corporation
    Inventors: Robert P. Meagley, Michael D. Goodner, Robert E. Leet, Michael L. McSwiney
  • Patent number: 7235341
    Abstract: 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: Grant
    Filed: March 17, 2003
    Date of Patent: June 26, 2007
    Assignee: Fujifilm Corporation
    Inventor: Toru Fujimori
  • Patent number: 7232648
    Abstract: A photosensitive resin composition comprising a resin (A1) having fluorine atom-containing groups, silicon atom-containing groups and ethylenic double bonds, a radical initiator (B) and an alkali-soluble photosensitive resin (D) having at least three ethylenic double bonds per molecule. Further, a photosensitive resin composition comprising a resin (A2) having fluorine atom-containing groups and ethylenic double bonds, a resin (A3) having silicon atom-containing groups and ethylenic double bonds, a radical initiator (B), and an alkali-soluble photosensitive resin (D) having at least three ethylenic double bonds per molecule.
    Type: Grant
    Filed: September 7, 2005
    Date of Patent: June 19, 2007
    Assignee: Asahi Glass Company, Limited
    Inventors: Hideyuki Takahashi, Kenji Ishizeki
  • Patent number: 7232639
    Abstract: As a polymer exhibiting improved transparency which is suitable for a resist resin used in a chemical-amplification-type resist being applicable for photolithography using exposure light at 180 nm or shorter, this invention provides a polymer comprising a repeating unit resulting from polymerization of a monomer exhibiting a polymerization activity, wherein the monomer has a fluorine-containing acetal or ketal structure represented by general formula (1): wherein R represents an atomic group containing a carbon-carbon double bond exhibiting polymerization activity; at least one of R1 and R2 is fluorinated alkyl group or fluorinated aryl group having 1 to 20 carbon atoms; and R3 represents a radical selected from the group consisting of hydrogen atom, alkyl group, alkoxy-substituted alkyl group, fluorinated alkyl group, aryl group, fluorinated aryl group, aralkyl group and fluorinated aralkyl group having 1 to 20 carbon atoms.
    Type: Grant
    Filed: February 25, 2003
    Date of Patent: June 19, 2007
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Kaichiro Nakano
  • Patent number: 7217496
    Abstract: A photoresist composition including a polymer is disclosed, wherein the polymer includes at least one monomer having the formula: where R1 represents hydrogen (H), a linear, branched or cyclo alkyl group of 1 to 20 carbons, a semi- or perfluorinated linear, branched or cyclo alkyl group of 1 to 20 carbons or CN; R2 represents an alicyclic group of 5 or more carbon atoms; X represents a methylene, ether, ester, amide or carbonate linkage; R3 represents a linear or branched alkylene group or semi- or perfluorinated linear or branched alkylene group with 1 or more carbon atoms; R4 represents hydrogen (H), methyl (CH3), trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perflourinated aliphatic group; R5 represents trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated substituted or unsubstituted aliphatic group; n represents an integer of 1 or more; and OR12 represents OH or at least one acid labile group selected from a tertiary alkyl c
    Type: Grant
    Filed: November 12, 2004
    Date of Patent: May 15, 2007
    Assignee: International Business Machines Corporation
    Inventors: Mahmoud Khojasteh, Pushkara Rao Varanasi, Wenjie Li, Kuang-Jung J Chen, Kaushal S. Patel
  • Patent number: 7217495
    Abstract: Fluorinated polymers, photoresists and associated processes for microlithography are described. These polymers and photoresists are comprised of a fluoroalcohol functional group which simultaneously imparts high ultraviolet (UV) transparency and developability in basic media to these materials. The materials of this invention have high UV transparency, particularly at short wavelengths, e.g., 157 nm, which makes them highly useful for lithography at these short wavelengths.
    Type: Grant
    Filed: July 9, 2004
    Date of Patent: May 15, 2007
    Assignee: E I. du Pont de Nemours and Company
    Inventors: Andrew Edward Feiring, Jerald Feldman, Frank Leonard Schadt, III
  • Patent number: 7211366
    Abstract: The present invention relates to a photoresist composition comprising a photoacid generator and at least one polymer comprising at least one unit as described by structure 1, The invention also relates to a process for imaging the photoresist composition of the present invention, and to a process of making the polymer in the presence of an organic base.
    Type: Grant
    Filed: September 9, 2003
    Date of Patent: May 1, 2007
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Ralph R. Dammel, Raj Sakamuri, Francis M. Houlihan
  • Patent number: 7211365
    Abstract: New negative-acting photoresist compositions are provided that are particularly useful for imaging at short wavelengths, particularly sub-200 nm wavelengths such as 193 nm. Resists of the invention provide contrast between exposed and unexposed coating layer regions through crosslinking or other solubility switching mechanism. Preferred resists of the invention include a resin component that contains repeat units that facilitate aqueous base solubility.
    Type: Grant
    Filed: March 4, 2003
    Date of Patent: May 1, 2007
    Assignee: Shipley Company, L.L.C.
    Inventors: George G. Barclay, Nicola Pugliano
  • Patent number: 7205086
    Abstract: 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-dimethyl-1,3-dioxole) and CX2?CY2; and (e) nitr
    Type: Grant
    Filed: November 26, 2001
    Date of Patent: April 17, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Larry L. Berger, Frank L. Schadt, III
  • 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: 7202009
    Abstract: This invention relates to resins and photoresist compositions that comprise such resins. Preferred polymers of the invention comprise adjacent saturated carbon atoms, either integral or pendant to the polymer backbone, that have a substantially gauche conformation. Polymers of the invention are particularly useful as a resin binder component of chemically-amplified positive-acting resists that can be effectively imaged at short wavelengths such as sub-200 nm and preferably about 157 nm. In such short-wavelength imaging applications, polymers of the invention that have a population of dihedral angles of adjacent saturated carbon atoms that are enriched in substantially gauche conformations can provide reduced undesired absorbance of the high energy exposure radiation.
    Type: Grant
    Filed: September 8, 2001
    Date of Patent: April 10, 2007
    Assignee: Shipley Company, L.L.C.
    Inventors: Peter Trefonas, III, Gary N. Taylor, Charles R. Szmanda
  • Patent number: 7202010
    Abstract: A chemical amplification type positive resist composition, which can reduce cost steeply without significantly decreasing basic abilities, is provided, and the chemical amplification type positive resist composition includes (A) a resin having a polymerization unit derived from p-hydroxystyrene and a polymerization unit of the formula (1) or formula (2) which is insoluble or poorly soluble itself in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, (B) a resin obtained by protecting a portion of the hydroxyl groups in poly(p-hydroxystyrene) with a protective group not dissociating by the action of an acid or a resin obtained by substituting a portion of the hydroxyl groups in poly(p-hydroxystyrene) with hydrogen, and (C) an acid generating agent.
    Type: Grant
    Filed: September 26, 2002
    Date of Patent: April 10, 2007
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Airi Yamada, Masumi Suetsugu, Yasunori Uetani