Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
  • Patent number: 7316884
    Abstract: A 5-methylene-1,3-dioxolan-4-one derivative and a monomer and copolymer thereof and a resist composition containing the polymer or copolymer where the 5-methylene-1,3 -dioxolan-4-one derivative is of formula (1): wherein R1 represents a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms, or a linear or branched alkyl group containing 1 to 6 carbon atoms which has a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms as a substituent; R2 represents a hydrogen atom, or a linear or branched alkyl group containing 1 to 6 carbon atoms; or R1 and R2 represent a bridged cyclic hydrocarbon group containing 4 to 16 carbon atoms together with the carbon atom to which they are bound, provided that the alkyl group and the bridged cyclic hydrocarbon group may have at least one substituent selected from a group consisting of a linear or branched alkyl group containing 1 to 6 carbon atoms which may be optionally substituted, a hydroxy group, a carboxy group, an acyl group containing 2 to 6 car
    Type: Grant
    Filed: October 22, 2002
    Date of Patent: January 8, 2008
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Ryuichi Ansai, Yoshihiro Kamon, Tadayuki Fujiwara, Hideaki Kuwano, Atsushi Ootake, Hikaru Momose
  • Patent number: 7316885
    Abstract: There are provided a method of forming a resist pattern that enables the resist pattern to be formed with good control of the pattern size, as well as a positive resist composition used in the method, and a layered product formed using the positive resist composition. In the above method a positive resist composition comprising a resin component (A), which contains a structural unit (a1) derived from a (meth)acrylate ester represented by a general formula (I) shown below, and displays increased alkali solubility under action of acid, and an acid generator component (B) that generates acid on exposure is applied to a substrate, a prebake is conducted, the resist composition is selectively exposed, post exposure baking (PEB) is conducted, alkali developing is then used to form a resist pattern, and the pattern size of the thus produced resist pattern is then narrowed by heat treatment.
    Type: Grant
    Filed: December 1, 2003
    Date of Patent: January 8, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Hideo Hada, Miwa Miyairi, Naotaka Kubota, Takeshi Iwai
  • Patent number: 7314701
    Abstract: A positive tone radiation-sensitive resin composition comprising (A) a 1-substituted imidazole, (B) a photoacid generator, and (C-a) a resin protected by an acid-dissociable group, insoluble or scarcely soluble in alkali, but becoming soluble in alkali when the acid-dissociable group dissociates or (C-b) an alkali-soluble resin and an alkali solubility controller, and a negative tone radiation-sensitive resin composition comprising (A), (B), (D) an alkali-soluble resin, and (E) a compound that can crosslink the alkali-soluble resin in the presence of an acid. The radiation-sensitive resin composition of the present invention is a chemically amplified resist exhibiting high resolution and high storage stability as a composition, and suitable for microfabrication sensible to active radiations, for example, ultraviolet rays such as g-lines and i-lines, deep ultraviolet rays represented by a KrF excimer laser, ArF excimer laser, F2 excimer laser, and EUV excimer laser, and electron beams.
    Type: Grant
    Filed: October 7, 2003
    Date of Patent: January 1, 2008
    Assignee: JSR Corporation
    Inventors: Kenichi Yokoyama, Fumihisa Miyajima, Tomoki Nagai, Eiji Yoneda
  • 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: 7312014
    Abstract: The present invention relates to a resist composition for practical use with high resolution, high sensitivity, superior pattern profile and no outgas in energy irradiation under high vacuum, suitable to an ultra-fine processing technology represented by use of electron beam and the like, and provides: (1) a resist composition comprising at least one kind of polymer containing, as components thereof, a monomer unit represented by the following general formula [1]: a monomer unit represented by the following general formula [2]: and a monomer unit represented by the following general formula [3]: at least one kind of compound to generate an acid by irradiation of radioactive ray, represented by the following general formula [4]; an organic basic compound; and a solvent, (2) the resist composition in accordance with (1), further containing a polymer unit represented by the following general formula [13]: and, (3) the resist composition in accordance with (1) and (2), further containing a comp
    Type: Grant
    Filed: June 21, 2002
    Date of Patent: December 25, 2007
    Assignee: Wako Pure Chemical Industries Ltd.
    Inventors: Tsuneaki Maesawa, Fumiyoshi Urano
  • Patent number: 7309750
    Abstract: Cyanoadamantyl compounds, polymers that comprise polymerized units of such compounds, and photoresist compositions that comprise such polymers are provided. Preferred polymers of the invention are employed in photoresists imaged at wavelengths less than 250 nm such as 248 nm and 193 nm.
    Type: Grant
    Filed: March 8, 2005
    Date of Patent: December 18, 2007
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Young C. Bae, Robert J. Kavanagh
  • Patent number: 7291443
    Abstract: A polymerizable composition contains (A) a dye which is soluble in an organic solvent and in an alkaline aqueous solution and has an absorption in 700 to 1200 nm, (B) a radical polymerization initiator, (C) a compound having an ethylenically unsaturated bond, and (D) a binder polymer.
    Type: Grant
    Filed: July 28, 2004
    Date of Patent: November 6, 2007
    Assignee: FUJIFILM Corporation
    Inventor: Kazuto Shimada
  • 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: 7291441
    Abstract: A positive resist composition comprising: a resin that comprises a repeating unit including a specific norbornane lactone structure and a repeating unit including a specific alicyclic hydrocarbon structure, and that increases a solubility of the resin in an alkaline developer by an action of an acid; and a compound that generates an acid upon treatment with one of an actinic ray and radiation, and a pattern forming method utilizing the same.
    Type: Grant
    Filed: August 25, 2005
    Date of Patent: November 6, 2007
    Assignee: Fujifilm Corporation
    Inventor: Kenichiro Sato
  • Patent number: 7288345
    Abstract: A photosensitive colored composition contains a resin, a monomer and a colorant. The resin is a copolymer resin of at least one compound (a) represented by general formula (I) below with at least one other compound (b) having an ethylenically unsaturated double bond: where R1 represents H or CH3, R2 represents an alkylene group having 2 or 3 carbon atoms, R3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may contain a benzene ring, and n is an integer of 1 to 15.
    Type: Grant
    Filed: March 31, 2005
    Date of Patent: October 30, 2007
    Assignees: Toyo Ink Mfg. Co., Ltd., Toppan Printing Co., Ltd.
    Inventors: Yukiyoshi Jonoshita, Tadashi Tanoue, Takeshi Itoi, Mizuhiro Tani
  • 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: 7282316
    Abstract: Provided are sulfonyldiazomethane compounds and photoacid generators suited for resist materials which generate less foreign matters after application, development and peeling, and in particular, are excellent in the pattern profile after the development; and resist materials and patterning process using them. Provided are sulfonyldiazomethane compounds represented by formula (1): Also provides are photoacid generators containing the sulfonyldiazomethane compounds, and a chemical amplification resist material comprising (A) a resin which changes its solubility in an alkali developer by action of an acid, and (B) a sulfonyldiazomethane compound of formula (1) capable of generating an acid by exposure to radiation. Provided is a patterning process comprising steps of applying the above-described resist material onto a substrate to form a coating, heating the coating, exposing the coating, and developing the exposed coating in a developer after an optional heat treatment.
    Type: Grant
    Filed: August 27, 2004
    Date of Patent: October 16, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Eiji Fukuda, Shigeo Tanaka
  • Patent number: 7279265
    Abstract: A positive resist composition comprising (A) a resin capable of increasing its solubility in an alkali developer under action of an acid, wherein the resin contains a repeating unit originated in an acrylic acid ester derivative in an amount of 50 to 100 mol % based on all repeating units and has a repeating unit having a specific lactone structure and a repeating unit having a monohydroxyadamantane or dihydroxyadamantane structure, (B) a compound of generating an acid upon irradiation with actinic rays or radiation, and (C) an organic solvent, and a pattern formation method using the composition.
    Type: Grant
    Filed: March 18, 2004
    Date of Patent: October 9, 2007
    Assignee: FujiFilm Corporation
    Inventors: Makoto Momota, Hajime Nakao
  • Patent number: 7279266
    Abstract: A photosensitive composition comprising: (A) a polymerizable compound represented by the following formula (I): A—{O—[(CH(—R1)CH(—R2))m—O]n—C(?O)—C(—R3)?CH2}p??(I) wherein R1, R2and R3 each represents a hydrogen atom or a methyl group, A represents a polyhydric alcohol residue or a polyhydric phenol residue, m represents an integer of from 1 to 6, n represents an integer of from 1 to 20, and p represents an integer of from 1 to 6; (B) an infrared absorber; and (C) an onium salt.
    Type: Grant
    Filed: September 23, 2004
    Date of Patent: October 9, 2007
    Assignee: FUJIFILM Corporation
    Inventors: Hiromitsu Yanaka, Takahiro Goto
  • Patent number: 7279256
    Abstract: Photoresist polymers and photoresist compositions are disclosed. A photoresist polymer comprising a polymerization repeating unit represented by Formula I is less sensitive to change in the amount of energy due to its higher active energy than that of a conventional photoresist polymer. As a result, a phenomenon where the portion of the pattern for the storage electrode contact region that receives relatively large amount of light becomes too thin is avoided when the device isolation film pattern is formed, and wherein pattern collapse caused by a high aspect ratio due to high etching resistance is prevented or avoided. wherein R1–R10, a, b, c and d are as defined in the description.
    Type: Grant
    Filed: May 9, 2005
    Date of Patent: October 9, 2007
    Assignee: Hynix Semiconductor Inc.
    Inventor: Min Seok Son
  • Patent number: 7279539
    Abstract: A polymer, which contains a structural unit having a carboxyl group represented by the following formula (1) at a side chain of the structural unit, wherein node position is formed, when the polymer is dissolved in an alkali aqueous solution having a pH of 10 or more and kept at 25° C. for 60 days: wherein R1 represents a hydrogen atom or a methyl group; R2 represents an (n+1)-valent organic linking group containing an ester group represented by —O(C?O)—; A represents an oxygen atom or NR3—; R3 represents a hydrogen atom, or an monovalent hydrocarbon group having from 1 to 10 carbon atoms; and n indicates an integer of from 1 to 5.
    Type: Grant
    Filed: June 29, 2006
    Date of Patent: October 9, 2007
    Assignee: Fujifilm Corporation
    Inventors: Atsushi Sugasaki, Kazuto Kunita
  • 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: 7270936
    Abstract: A negative resist composition and a method for patterning semiconductor devices using the composition are provided. The negative resist composition contains an alkali-soluble hydroxy-substituted base polymer, a silicon-containing crosslinker having an epoxy ring, and a photoacid generator. In the method for patterning semiconductor devices, fine patterns are formed according to a bi-layer resist process using the negative resist composition.
    Type: Grant
    Filed: July 6, 2005
    Date of Patent: September 18, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventor: Sang-Jun Choi
  • Patent number: 7270935
    Abstract: Cyanoadamantyl compounds, polymers that comprise polymerized units of such compounds, and photoresist compositions that comprise such polymers are provided. Preferred polymers of the invention are employed in photoresists imaged at wavelengths less than 250 nm such as 248 nm and 193 nm.
    Type: Grant
    Filed: March 8, 2005
    Date of Patent: September 18, 2007
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Young C. Bae, Robert J. Kavanagh
  • Patent number: 7270916
    Abstract: Disclosed is a recording medium comprising a recording layer including a photo-acid generating agent that generates an acid upon irradiation with an actinic radiation and a polymer having a polymerizable substituent group bonded to a main chain of the polymer via a functional group that cleaves in the presence of the acid.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: September 18, 2007
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Naoko Kihara, Urara Ichihara, legal representative, Akiko Hirao, Kazuki Matsumoto, Hideyuki Nishizawa, Katsutaro Ichihara, deceased
  • 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: 7261998
    Abstract: The present invention provides an imageable element including a lithographic substrate and an imageable layer disposed on the substrate. The imageable layer includes a radically polymerizable component, an initiator system capable of generating radicals sufficient to initiate a polymerization reaction upon exposure to imaging radiation, and a polymeric binder having a hydrophobic backbone and including both constitutional units having a pendant cyano group attached directly to the hydrophobic backbone, and constitutional units having a pendant group including a hydrophilic poly(alkylene oxide) segment. When the imageable element is imaged and developed, the resulting printing plate may exhibit improved on-press solvent resistance and longer press life.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: August 28, 2007
    Assignee: Eastman Kodak Company
    Inventors: Kouji Hayashi, Heidi M. Munnelly, Ting Tao, Jianbing Huang, Shashikant Saraiya
  • 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: 7258963
    Abstract: In a photosensitive resin, a photoresist composition having the photosensitive resin, and a method of forming a photoresist pattern by using the photoresist, the photosensitive resin includes a blocking group substituted for an acid. The photosensitive resin has a weight-average molecular weight of from about 6,000 up to about 8,000. The photosensitive resin has a blocking ratio of from about 5% up to about 40%.
    Type: Grant
    Filed: January 17, 2006
    Date of Patent: August 21, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Youn-Kyung Wang, Kyoung-Mi Kim, Young-Ho Kim, Jae-Hyun Kim
  • 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: 7255972
    Abstract: A photosensitive resin composition suitable for forming a thick film and an ultra-thick film used for forming a thick resist pattern used in the process of forming a magnetic pole on a magnetic head and a bump, which comprises (A) an alkali soluble novolak resin, (B) an alkali soluble acrylic resin, (C) an acetal compound, and (D) an acid generator.
    Type: Grant
    Filed: October 16, 2003
    Date of Patent: August 14, 2007
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Yoshinori Nishiwaki, Toshimichi Makii
  • Patent number: 7250246
    Abstract: A positive resist composition which can be suitably used in an ultramicrolithography process such as production of VLSI or high-capacity microchip and in other photofabrication processes and can ensure good sensitivity, resolution, pattern profile and line edge roughness when irradiated with actinic rays or radiation, particularly, electron beam, X-ray or EUV; and a pattern formation method using the composition, are provided, the positive resist composition comprising (A) a resin comprising a specific acryl-based repeating unit and a specific styrene-based repeating unit, which increases the dissolution rate in an alkali developer by the action of an acid, (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation, and (C) a solvent; and a pattern formation method using the composition.
    Type: Grant
    Filed: January 25, 2005
    Date of Patent: July 31, 2007
    Assignee: Fujifilm Corporation
    Inventor: Kazuyoshi Mizutani
  • Patent number: 7247418
    Abstract: Both single-layer and multilayer imageable elements have a substrate and at least one imageable layer. The elements can be used to prepare either negative- or positive-working imaged elements, for example as lithographic printing plates. The imageable elements also include a radiation absorbing compound and a solvent-resistant polymer comprising pendant phosphoric acid groups, pendant adamantyl groups, or both. When this polymer comprises pendant adamantyl groups, they are connected to the polymer backbone through a urea or urethane group. The imageable elements have improved chemical resistance and thermal bakeability from the presence of the unique solvent-resistant polymer.
    Type: Grant
    Filed: December 1, 2005
    Date of Patent: July 24, 2007
    Assignee: Eastman Kodak Company
    Inventors: Shashikant Saraiya, Jayanti Patel, Ting Tao, Kevin B Ray, Frederic E. Mikell, James L. Mulligan, John Kalamen, Scott A. Beckley, Eric Clark
  • Patent number: 7241554
    Abstract: The photosensitive composition of the invention contains a polymer material having a group having a structure represented by following general formula (2), and a photo acid generator generating acid with an ultraviolet ray or an ionizing radiation wherein m represents an integer of 0 or more.
    Type: Grant
    Filed: June 10, 2005
    Date of Patent: July 10, 2007
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Satoshi Saito
  • Patent number: 7241556
    Abstract: A positive-working imageable element comprises inner and outer layers and a radiation absorbing compound such as an IR absorbing dye. The inner layer includes a first polymeric material. The ink receptive outer layer includes a second polymeric binder comprising a polymer backbone and an —X—C(?T)—NR—S(?O)2— moiety that is attached to the polymer backbone, wherein —X— is an oxy or —NR?— group, T is O or S, R and R? are independently hydrogen, halo, or an alkyl group having 1 to 6 carbon atoms. After thermal imaging, the element can be developed using an alkaline developer. Use of the particular second polymeric binder reduces sludging in the developer. Its dissolution rate in the developer is slow enough to resist developer attack in the non-imaged areas of the outer layer but rapid enough for the second polymeric binder to be quickly loosened from imaged areas and kept suspended or dissolved for a considerable time.
    Type: Grant
    Filed: October 23, 2006
    Date of Patent: July 10, 2007
    Assignee: Eastman Kodak Company
    Inventors: Shashikant Saraiya, Anthony P. Kitson, Frederic E. Mikell, Larisa Novoselova
  • 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: 7235342
    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 hydroxy-containing additive; and a resist polymer derived from at least one first monomer. The resist polymer may be further derived from a second monomer having an aqueous base soluble moiety. The hydroxy-containing additive has the structure of Q—OH, where Q may include one or more cyclic structures. Q—OH may have a primary alcohol structure. 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: January 28, 2004
    Date of Patent: June 26, 2007
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara R. Varanasi
  • 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: 7232642
    Abstract: The present invention provides a chemically amplified positive resist composition comprising (A) a resin which comprises (i) at least one structural unit selected from the group consisting of structural units of the formulas (no and (V), (ii) a structural unit of the formula (I) and (iii) a structural unit of the formula (II), and (B) an acid generator.
    Type: Grant
    Filed: May 6, 2005
    Date of Patent: June 19, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ichiki Takemoto, Kazuhiko Hashimoto, Takayuki Miyagawa
  • Patent number: 7232647
    Abstract: The present invention provides a photosensitive resin composition for laser scanning exposure, which satisfies the following formula (1): - 25 ? E 1 - E 0 E 0 × 100 ? 25 ( 1 ) wherein E0 represents an exposure amount in mJ/cm2 at which the photosensitive resin composition is cured at the 21st step of the density 1.00 of a 41-step step tablet having a density range from 0.00 to 2.00, a density step of 0.05, a tablet size of 20 mm×187 mm and a step size of 3 mm×12 mm, by irradiation with a full wavelength active light of a high pressure mercury lamp and E1 represents an exposure amount in mJ/cm2 at which the photosensitive resin composition after being left for 2 hours under 40 W non-ultraviolet white lamp is cured at the 21st step of the 41-step step tablet by irradiation with a full wavelength active light from a high pressure mercury lamp.
    Type: Grant
    Filed: March 21, 2005
    Date of Patent: June 19, 2007
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Yasuhara Murakami, Takahiro Hidaka
  • 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: 7223516
    Abstract: A positive type photoresist composition suitable for light in the wavelength region of 170 nm to 220 nm, high in sensitivity, excellent in adhesion and giving a good resist pattern profile, which comprises a resin having an ester group represented by the following general formula [I] in its molecule and a compound generating an acid by irradiation of an active light ray or radiation: wherein R1 represents a hydrogen atom, an alkyl group or a cycloalkyl group; and R2 and R3, which may be the same or different, each represents a hydrogen atom, an alkyl group, a cycloalkyl group or -A-R4, and R2 and R3 may combine together to form a ring, wherein R4 represents a hydrogen atom, an alkyl group or a cycloalkyl group, R4 and R2 or R3 may combine together to form a ring, and A represents an oxygen atom or a sulfur atom.
    Type: Grant
    Filed: December 6, 2000
    Date of Patent: May 29, 2007
    Assignee: Fujifilm Corporation
    Inventors: Kenichiro Sato, Toshiaki Aoai
  • Patent number: 7223506
    Abstract: Single-layer and multilayer imageable elements have a substrate and at least one imageable layer and can be used to prepare positive-working lithographic printing plates. The imageable elements also include a radiation absorbing compound and a solvent-resistant polymer binder comprising an —N(R)—C(?X)—N(R?)—S(?O)2— moiety that is attached to the polymer backbone, wherein X is O or S, R and R? are independently hydrogen, halo, or an alkyl group having 1 to 6 carbon atoms. This solvent-resistant polymer binder is located in the imageable layer closest to the substrate and provides improved chemical resistance.
    Type: Grant
    Filed: March 30, 2006
    Date of Patent: May 29, 2007
    Assignee: Eastman Kodak Company
    Inventors: Anthony P. Kitson, Shashikant Saraiya, Kevin B. Ray, James L. Mulligan, Frederic E. Mikell, Larisa Novoselova, Eric Clark
  • Patent number: 7220532
    Abstract: The present invention provides a chemical amplification type positive resist composition comprising a nitrogen containing compound of the formula (VIa) or (VIb); resin which contains a structural unit having an acid labile group and 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 an acid generator of the formula (I)
    Type: Grant
    Filed: September 9, 2003
    Date of Patent: May 22, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiyuki Takata, Isao Yoshida, Hirotoshi Nakanishi
  • Patent number: 7220533
    Abstract: The present invention provides a photosensitive resin composition for laser scanning exposure, which satisfies the following formula (1): - 25 ? E 1 - E 0 E 0 × 100 ? 25 ( 1 ) wherein E0 represents an exposure amount in mJ/cm2 at which the photosensitive resin composition is cured at the 21st step of the density 1.00 of a 41-step step tablet having a density range from 0.00 to 2.00, a density step of 0.05, a tablet size of 20 mm×187 mm and a step size of 3 mm×12 mm, by irradiation with a full wavelength active light of a high pressure mercury lamp and E1 represents an exposure amount in mJ/cm2 at which the photosensitive resin composition after being left for 2 hours under 40 W non-ultraviolet white lamp is cured at the 21st step of the 41-step step tablet by irradiation with a full wavelength active light from a high pressure mercury lamp.
    Type: Grant
    Filed: March 21, 2001
    Date of Patent: May 22, 2007
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Yasuharu Murakami, Takahiro Hidaka
  • Patent number: 7217491
    Abstract: An antireflective coating composition including a polyester and/or a polyurethane; and a crosslinker selected from the group consisting of tetraamidomethyl ethers.
    Type: Grant
    Filed: June 5, 2003
    Date of Patent: May 15, 2007
    Assignee: Battelle Memorial Institute
    Inventors: Vincent D. McGinniss, Steven M. Risser, Jeffrey T. Cafmeyer, James L. White, Bhima R. Vijayendran
  • 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: 7217498
    Abstract: A heat-sensitive lithographic printing plate precursor comprising a support having thereon two image-forming layers each containing a polymer insoluble in water and soluble in an aqueous alkaline solution, wherein an upper layer of the image-forming layers contains a copolymer including a monomer unit represented by formula (A) defined in the specification.
    Type: Grant
    Filed: December 23, 2003
    Date of Patent: May 15, 2007
    Assignee: Fujifilm Corporation
    Inventors: Ikuo Kawauchi, Ippei Nakamura, Mitsumasa Tsuchiya
  • Patent number: 7214466
    Abstract: The invention is directed to a photoimageable composition comprising: (I) finely divided particles of inorganic material comprising: (a) functional phase particles selected from electrically conductive, resistive, and dielectric particles; (b) inorganic binder having a glass transition temperature in the range of from 325 to 600° C., a surface area of no greater than 10 m2/g and at least 85 wt. % of the particles having a size of 0.1–10 ?m; dispersed in: (II) an organic medium comprising: (a) aqueous developable polymer which is a copolymer, interpolymer or mixture thereof, wherein each copolymer or interpolymer comprises (1) a nonacidic comonomer comprising a C1-10 alkyl acrylate, C1-10 alkyl methacrylate, styrenes, substituted styrenes or combinations thereof and (2) an acidic comonomer comprising ethylenically unsaturated carboxylic acid containing moiety; (g) cationically polymerizable monomer; (h) photoinitiation system; and (i) organic solvent.
    Type: Grant
    Filed: December 14, 2005
    Date of Patent: May 8, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Haixin Yang, Mark R. McKeever
  • Patent number: 7214465
    Abstract: A positive photosensitive composition comprising (A1) a compound that generates an aromatic sulfonic acid substituted with at least one fluorine atom and/or a group having at least one fluorine atom upon irradiation of an actinic ray or radiation, (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase solubility in an alkali developing solution, and (C) a compound that has at least three hydroxy or substituted hydroxy groups and at least one cyclic structure or (A2) an onium salt of an alkanesulfonic acid in which the ?-position of the sulfonic acid is not substituted with a fluorine atom and/or an onium salt of a carboxylic acid.
    Type: Grant
    Filed: January 9, 2003
    Date of Patent: May 8, 2007
    Assignee: Fujifilm Corporation
    Inventors: Hajime Nakao, Yasumasa Kawabe, Toru Fujimori, Kunihiko Kodama
  • Patent number: 7214471
    Abstract: The photosensitive resin film in an uncured state of the invention comprises (A) a specific alkali-soluble copolymer, (B) a compound having at least one ethylenically unsaturated double bond and (C) a radiation-sensitive radical polymerization initiator by the use of which a coating film having a dry film thickness of 70 ?m in an uncured state has a 365 nm radiation transmittance of not less than 10% and a 405 nm radiation transmittance of not less than 60%, contains the radiation-sensitive radical polymerization initiator (C) in an amount of 20 to 40 parts by weight based on 100 parts by weight of the component (A), and has a dry film thickness of not less than 50 ?m. According to the photosensitive resin film, a high bump having a height of not less than 50 ?m can be readily formed on a chip substrate with high precision though formation of such a high bump is difficult by the conventional technique. Moreover, connection failure of an element can be inhibited, and reliability of an element can be enhanced.
    Type: Grant
    Filed: March 25, 2004
    Date of Patent: May 8, 2007
    Assignee: JSR Corporation
    Inventors: Shin-ichiro Iwanaga, Tooru Kimura, Kouji Nishikawa
  • 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: 7208260
    Abstract: The present invention discloses a cross-linking monomer represented by the following Chemical Formula 1, a process for preparing a photoresist polymer using the same, and said photoresist polymer: <Chemical Formula> wherein, R? and R? individually represent hydrogen or methyl; m represents a number of 1 to 10; and R is selected from the group consisting of straight or branched C1-10 alkyl, straight or branched C1-10 ester, straight or branched C1-10 ketone, straight or branched C1-10 carboxylic acid, straight or branched C1-10 acetal, straight or branched C1-10 alkyl including at least one hydroxyl group, straight or branched C1-10 ester including at least one hydroxyl group, straight or branched C1-10 ketone including at least one hydroxyl group, straight or branched C1-10 carboxylic acid including at least one hydroxyl group, and straight or branched C1-10 acetal including at least one hydroxyl group.
    Type: Grant
    Filed: February 22, 2002
    Date of Patent: April 24, 2007
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Keun Kyu Kong, Min Ho Jung, Geun Su Lee, Ki Ho Balk
  • 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