Radiation-sensitive Composition Patents (Class 430/170)
  • Patent number: 7026091
    Abstract: A positive photoresist with uniform reactivity for use in a thick film lithography process, includes thermal curing during soft-baking and photo dissociation through UV exposure. The positive photoresist comprises a phenolic resin, a resin with acid labile groups, a photoacid generator (PAG), and a reactive monomer with vinyl ether or epoxy group. First, the resins react with the reactive monomer to perform a thermal curing step by soft-baking to form network polymers. In the UV lithography process, the exposed network polymers perform both deprotection and depolymerization simultaneously and are rendered alkali-soluble. The resulting photoresist patterns have a high aspect ratio and resolution profile, due to the good alkali dissolution contrast and uniform reactivity.
    Type: Grant
    Filed: July 22, 2004
    Date of Patent: April 11, 2006
    Assignee: Industrial Technology Research Institute
    Inventors: Wei-Chan Tseng, Tsing-Tang Song, Chih-Shin Chuang, Kuen-Yuan Hwang, An-Pang Tu
  • Patent number: 7015256
    Abstract: A photosensitive composition for forming a dielectric of the present invention comprising inorganic particles, an alkali developable resin and additives, wherein the additives comprise a compound having a quinonediazido group (C1), a compound containing at least two alkyletherified amino groups in the molecule (C2) and a thermal acid generator (C3), or wherein the inorganic particles comprise inorganic superfine particles (A-I) having a mean particle diameter of less than 0.05 ?m and inorganic fine particles (A-II) having a mean particle diameter of not less than 0.05 ?m. The composition can be calcined at low temperatures to form a dielectric layer with high dimensional precision, said layer having a high dielectric constant and a low dielectric loss. Also provided are a dielectric and an electronic part prepared from the composition.
    Type: Grant
    Filed: December 26, 2002
    Date of Patent: March 21, 2006
    Assignee: JSR Corporation
    Inventors: Nobuyuki Ito, Hideaki Masuko, Satomi Hasegawa, Atsushi Ito, Katsumi Inomata
  • Patent number: 7005229
    Abstract: A method of multiphoton photosensitizing comprises (a) providing a multiphoton-activatable, photoreactive composition comprising (1) at least one reactive species that is capable of undergoing an acid- or radical-initiated chemical reaction, and (2) a photoinitiator system comprising photochemically-effective amounts of (i) at least one type of semiconductor nanoparticle that has at least one electronic excited state that is accessible by absorption of two or more photons, and (ii) a composition that is capable of interacting with the excited state of the semiconductor nanoparticle to form at least one reaction-initiating species; and (b) irradiating the multiphoton-activatable, photoreactive composition with light sufficient to cause absorption of at least two photons, thereby inducing at least one acid- or radical-initiated chemical reaction where the composition is exposed to the light.
    Type: Grant
    Filed: October 2, 2002
    Date of Patent: February 28, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: Manoj Nirmal, Catherine A. Leatherdale, David S. Arney
  • Patent number: 6927274
    Abstract: Polyimide precursors contained in resin compositions of the present invention have a polymer structure unit represented by formula (1) below: wherein chemical structure A2 includes an alicyclic compound but not an aromatic compound such as a benzene ring so that they provide excellent light transmission over a wide wavelength range. The polyimide precursors are imidized at 7.5% or more and 36% or less so that they are less soluble in developing solutions and therefore are not dissolved in the developing solutions at unexposed parts. Thus, the resin compositions of the present invention can be used to form a resin film having a precise pattern by exposure and development.
    Type: Grant
    Filed: October 24, 2003
    Date of Patent: August 9, 2005
    Assignee: Sony Chemicals Corp.
    Inventors: Mamiko Nomura, Masatoshi Hasegawa, Junichi Ishii, Tadashi Akamatsu
  • Patent number: 6924323
    Abstract: A compound shown by the general formula [1] (wherein R1, R2 and R3 are each independently an aromatic hydrocarbon residual group, Yn? is an anion derived from a carboxylic acid having 3 or more carbon atoms with substituted fluorine atoms, and n is 1 or 2, provided that R1, R2 and R3 each is not a phenyl group having substituents at an ortho and/or a meta position), and a composition consisting of the compound and a diazodisulfone compound are disclosed. Use of the compound or the compound as an acid generator for resists produces the effects of improving the profiles of ultra-fine patterns or diminishing sidewall irregularities in ultra-fine patterns. The compound is also useful as a cationic photopolymerization initiator.
    Type: Grant
    Filed: June 27, 2001
    Date of Patent: August 2, 2005
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Masami Ishihara, Motoshige Sumino, Kazuhito Fukasawa, Naoki Katano, Shigeaki Imazeki
  • 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: 6908727
    Abstract: This invention describes a heat sensitive composition comprising: (A-I) a compound which is represented by the following general formula (I) and generates a radical when heated, and (B-I) a compound having physical and chemical properties that are changed irreversibly by a radical, R—SO2?M+??General formula (I) wherein R represents an alkyl group or aryl group, and M+ represents a counter cation selected from sulfonium, iodonium, diazonium, ammonium and azinium; and a negative planographic printing plate precursor which can be recorded by heat mode using this composition. This invention also describes a planographic printing plate precursor comprising a substrate having disposed thereon a photosensitive layer containing (C-II) a light-heat converting agent, (B-II) a compound having a polymerizable unsaturated group, and (A-II) an onium salt having at least two cation parts in one molecule.
    Type: Grant
    Filed: March 11, 2004
    Date of Patent: June 21, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuto Shimada, Tadahiro Sorori, Morio Yagihara
  • Patent number: 6875554
    Abstract: A positive photosensitive polyimide resin composition comprising: (a) a solvent-soluble polyimide comprised of from 1 to 100 mol % of a bivalent organic group derived from a diamine, that has at least one solvent solubilizing functional group, the polyimide having a reduced viscosity ranging from 0.05 to 5.0 dl/g, (b) a photosensitive orthoquinonediazide compound, and (c) from 0.1 to 50 wt %, based on the total weight of all polymers of the composition, of a component (c1) or (c2), wherein: component (c1) is a solvent-soluble polyimide comprised of from 1 to 100 mol % of a bivalent organic group derived from a diamine, that has at least one functional group selected from the group consisting of a long chain alkyl group having at least 6 carbon atoms and a fluorinated alkyl group, the polyimide having a reduced viscosity ranging from 0.05 to 5.
    Type: Grant
    Filed: October 3, 2001
    Date of Patent: April 5, 2005
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Tadashi Hatanaka, Tomonari Nakayama, Takayasu Nihira
  • Patent number: 6846607
    Abstract: A carbazole derivative of the following formula (1), wherein R1 and R2 individually represent a hydrogen atom or a monovalent organic group, or R1 and R2 form, together with the carbon atom to which R1 and R2 bond, a divalent organic group having a 3-8 member carbocyclic structure or a 3-8 member heterocyclic structure, and R3 represents a hydrogen atom or a monovalent organic group. The carbazole derivative is suitable as an additive for increasing sensitivity of a chemically amplified resist. A chemically amplified radiation-sensitive resin composition, useful as a chemically amplified resist, comprising the carbazole derivative is also disclosed.
    Type: Grant
    Filed: March 5, 2002
    Date of Patent: January 25, 2005
    Assignee: JSR Corporation
    Inventors: Tomoki Nagai, Jun Numata, Shirou Kusumoto, Eiichi Kobayashi
  • Patent number: 6824948
    Abstract: A negative-working resist composition for electron beams or X-rays comprising (A) a compound generating an acid and/or radical species by the irradiation of electron beams or X-rays, (B) a resin which is insoluble in water and soluble in an alkali aqueous solution, (C) a crosslinking agent causing crosslinking with the resin of component (B) by the action of an acid, and (D) a compound having at least one unsaturated bond capable of being polymerized by an acid and/or a radical, and a negative-working resist composition for electron beams or X-rays comprising (A) a compound generating an acid and/or radical species by the irradiation of electron beams or X-rays, (B′) a resin having at least one unsaturated bond polymerizable by an acid and/or an alkali, which is insoluble in water but soluble in an alkali aqueous solution, and (C) a crosslinking agent causing crosslinking with the resin (B′) by the action of an acid are disclosed.
    Type: Grant
    Filed: January 16, 2001
    Date of Patent: November 30, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Yutaka Adegawa, Morio Yagihara
  • Patent number: 6824949
    Abstract: There are disclosed polybenzoxazole precursors which can be processed by centrifugal techniques, which can be cyclized to polybenzoxazoles on substrates without difficulty, and which after cyclization to polybenzoxazoles exhibit a high temperature stability. In particular, these precursors and the polybenzoxazoles prepared from them possess high resistance against the diffusion of metals.
    Type: Grant
    Filed: November 13, 2001
    Date of Patent: November 30, 2004
    Assignee: Infineon Technologies AG
    Inventors: Jörg Haussmann, Gerhard Maier, Günter Schmid, Recai Sezi
  • Publication number: 20040202954
    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: Application
    Filed: March 18, 2004
    Publication date: October 14, 2004
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Makoto Momota, Hajime Nakao
  • Patent number: 6790579
    Abstract: The present invention relates to a radiation sensitive photoresist composition comprising a photoacid initiator and a polycyclic polymer comprising repeating units that contain pendant acid labile groups. Upon exposure to an imaging radiation source the photoacid initiator generates an acid which cleaves the pendant acid labile groups effecting a polarity change in the polymer. The polymer is rendered soluble in an aqueous base in the areas exposed to the imaging source.
    Type: Grant
    Filed: August 2, 2000
    Date of Patent: September 14, 2004
    Assignee: Sumitomo Bakelite Co., Ltd.
    Inventors: Brian L. Goodall, Saikumar Jayaraman, Robert A. Shick, Larry F. Rhodes
  • Patent number: 6787282
    Abstract: A positive resist composition comprising (A) a resin, which increases a solubility rate in an alkali developing solution by the action of an acid, containing a repeating unit represented by formula (I) defined in the specification, a repeating unit represented by formula (II) defined in the specification and a repeating unit represented by formula (III) defined in the specification, and (B) a compound that generates an acid upon irradiation of an actinic ray or radiation.
    Type: Grant
    Filed: September 25, 2002
    Date of Patent: September 7, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Kenichiro Sato
  • Patent number: 6783912
    Abstract: New photoacid generator compounds (“PAGs”) are provided and photoresist compositions that comprise such compounds. In particular, non-ionic substituted disulfone compounds PAGS are provided, including disulfone PAGs that contain a diazo, substituted methylene or hydrazine moiety interposed between substituted sulfone groups. Also provided are positive- and negative-acting chemically amplified resists that contain such PAGs and that are preferably imaged with sub-300 nm or sub-200 nm radiation such as 248 nm, 193 nm, or 157 nm radiation.
    Type: Grant
    Filed: February 27, 2001
    Date of Patent: August 31, 2004
    Assignee: Shipley Company, L.L.C.
    Inventors: James F. Cameron, Gerhard Pohlers
  • Patent number: 6784275
    Abstract: Disclosed is an active energy ray-curable polyimide resin composition which comprises a polymerizable polyimide resin (I) having an isocyanurate ring, an alicyclic structure, an imide ring and a (meth)acryloyl group and being capable of patterning with a dilute alkali aqueous solution.
    Type: Grant
    Filed: June 27, 2002
    Date of Patent: August 31, 2004
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Eiju Ichinose, Yohzoh Yamashina, Hidenobu Ishikawa
  • Publication number: 20040166432
    Abstract: A chemical amplification type resist composition comprising a specific sulfonyldiazomethane containing long-chain alkoxyl groups has many advantages including improved resolution, improved focus latitude, minimized line width variation or shape degradation even on long-term PED, minimized debris left after coating, development and peeling, and improved pattern profile after development and is thus suited for microfabrication.
    Type: Application
    Filed: February 12, 2004
    Publication date: August 26, 2004
    Inventors: Youichi Ohsawa, Katsuhiro Kobayashi, Yoshitaka Yanagi, Kazunori Maeda
  • Patent number: 6746813
    Abstract: A negative resist composition comprising (A-1) an alkali-soluble resin containing a repeating unit represented by formula (1) defined in the specification, (A-2) an alkali-soluble resin containing a repeating unit represented by formula (2) defined in the specification, (B) a crosslinking agent crosslinking with the alkali-soluble resin (A-1) or (A-2) by the action of an acid, (C) a compound that generates an acid upon irradiation of an actinic ray or radiation, and (D) a nitrogen-containing basic compound.
    Type: Grant
    Filed: March 26, 2003
    Date of Patent: June 8, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shoichiro Yasunami, Yutaka Adegawa, Koji Shirakawa
  • Patent number: 6746985
    Abstract: A full-color heat-sensitive recording material. At least a heat-sensitive recording layer that color-develops to yellow color; a heat-sensitive recording layer that color-develops to cyan color and a heat-sensitive recording layer that color-develops to magenta color are sequentially provided on a support in this order from the support side. All of the above-mentioned heat-sensitive recording layers contain a diazo compound and/or diazonium salt, and a coupler compound that reacts with the diazo compound and/or diazonium salt for color development.
    Type: Grant
    Filed: April 26, 2002
    Date of Patent: June 8, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Shunsaku Higashi
  • Patent number: 6743562
    Abstract: A positive photoresist composition comprising the components of: (a) a resin which decomposes by the action of an acid, thereby having an increased solubility in an alkali developer; and (b) a compound which is represented by the formula (1) and generates an acid by exposure to active rays or radiation, and a compound which is represented by the formula (2) and generates an acid by exposure to active rays or radiation.
    Type: Grant
    Filed: March 15, 2002
    Date of Patent: June 1, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Mokoto Momota, Yasumasa Kawabe
  • Patent number: 6727032
    Abstract: A radiation-sensitive resin composition including (A) a resin containing an alicyclic skeleton in its backbone, and (B) a radiation-sensitive acid-generating agent, is provided. This composition is excellent in transparency with respect to radiation and dry etching resistance, and can give a photoresist pattern excellent in adhesion to substrates, sensitivity, resolution, and developability.
    Type: Grant
    Filed: February 7, 1997
    Date of Patent: April 27, 2004
    Assignee: JSR Corporation
    Inventors: Mitsuhito Suwa, Toru Kajita, Shin-ichiro Iwanaga, Toshiyuki Ota
  • Patent number: 6727033
    Abstract: A positive resist composition comprising a resin (A), which is decomposed by the action of an acid to increase solubility in an alkali developing solution, containing a structural unit including a group represented by formula (X) defined in the specification and/or a resin (B), which is decomposed by the action of an acid to increase solubility in an alkali developing solution, containing a structural unit including a group represented by formula (Y) defined in the specification, and a resin (C), which is decomposed by the action of an acid to increase solubility in an alkali developing solution, containing a structural unit including a group represented by formula (Q) defined in the specification; and a compound that generates an acid upon irradiation of an actinic ray or radiation.
    Type: Grant
    Filed: November 1, 2002
    Date of Patent: April 27, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Fumiyuki Nishiyama, Toru Fujimori
  • Patent number: 6723483
    Abstract: A triphenyl sulfonium salt compound shown by the general formula [1] or [3]. (wherein R1 and R2 are each independently a hydrogen atom or a lower alkyl group, provided that at least one of R1 and R2 are a lower alkyl group, R3s are each independently an alkyl group, n is an integer of 0 to 3, i is an integer of 1 to 3, j is an integer of 0 to 2, provided that i+j=3, Y− is an anion derived from a sulfonic acid shown by the general formula [2] R4—SO3H  [2] [wherein R4 is an alkyl group or an aryl group which may have as a substituent an alkyl group]). (wherein X is a phenyl group which has a substituent at an ortho- and/or a meta-position, m is an integer of 1 to 3, q is an integer of 0 to 2, provided that m+q=3, p is 1 or 2 and Zp− is an anion derived from a carboxylic acid).
    Type: Grant
    Filed: December 7, 2000
    Date of Patent: April 20, 2004
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Keiji Oono, Kazuhito Fukasawa, Kazunori Sakamoto, Fumiyoshi Urano, Motoshige Sumino, Shigeaki Imazeki
  • Patent number: 6723485
    Abstract: A positive resist composition contains (a) an acrylic resin which is subject to a change in solubility in a basic aqueous solution, the acrylic resin comprising an acrylic or methacrylic acid ester unit comprising an ester moiety comprising a fluorine-containing group; and (b) a photoacid generator capable of releasing an acid when irradiated with a laser. The composition is high in transparency to vacuum ultraviolet laser beams, particularly the F2 excimer laser beam, and high in sensitivity.
    Type: Grant
    Filed: November 28, 2000
    Date of Patent: April 20, 2004
    Assignee: Central Glass Company, Limited
    Inventors: Kentaro Tsutsumi, Michitaka Ootani, Kazuhiko Maeda
  • Patent number: 6713612
    Abstract: Sulfonyldiazomethane compounds containing a long-chain alkylcyclohexyl group are novel and useful as photoacid generators. Chemical amplification type resist compositions comprising the same are suited for microfabrication because of many advantages including improved resolution, improved focus latitude, minimized line width variation or shape degradation even on long-term PED, minimized debris left after coating, development and peeling, and improved pattern profile after development.
    Type: Grant
    Filed: May 1, 2003
    Date of Patent: March 30, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Koji Hasegawa, Takao Yoshihara, Kazunori Maeda, Toshihiko Fujii
  • Publication number: 20040048186
    Abstract: Disclosed is a thermally sensitive imagable article and compositions therefor. The imagable article comprises a coating on a substrate, the coating comprising an amino acid or amide, and a compound capable of generating an acid upon heating. The coating optionally comprises a radiation absorbing compound. When imagewise exposed the coating has the property that exposed regions become relatively insoluble in a developer liquid whereas regions that have not been exposed remain relatively soluble in the developer and dissolve in the developer, leaving the exposed substrate in those regions.
    Type: Application
    Filed: December 10, 2001
    Publication date: March 11, 2004
    Applicant: Kodak Polychrome Graphics LLC.
    Inventors: Gregory Turner, Denise Howard
  • Patent number: 6703178
    Abstract: The present invention discloses a chemical amplified photoresist composition including a polymer having a repeated unit of the formula (II), wherein R1 is H, haloalkyl group or C1-C4 alkyl group; R2 is hydroxyl group, C1-C8 alkoxy group or C1-C8 thioalkyl group; G is (CH2)n, O or S, wherein n is 0, 1, 2, 3 or 4; Rc is a lactone group; and m is 1, 2 or 3. The chemical amplified photoresist composition of the present invention can be applied to general lithography processes, and particularly to the lithography of ArF, KrF or the like light sources, and exhibit excellent resolution, figures and photosensitivity.
    Type: Grant
    Filed: May 28, 2002
    Date of Patent: March 9, 2004
    Assignee: Everlight USA, Inc.
    Inventors: Chi-Sheng Chen, Yen-Cheng Li, Meng-Hsum Cheng
  • Publication number: 20040033432
    Abstract: Sulfonyldiazomethane compounds containing a long-chain alkyl- or alkoxy-naphthyl group are novel and useful as photoacid generators. Chemical amplification type resist compositions comprising the same are suited for microfabrication because of many advantages including improved resolution, improved focus latitude, and minimized line width variation or shape degradation even on long-term PED.
    Type: Application
    Filed: August 8, 2003
    Publication date: February 19, 2004
    Inventors: Youichi Ohsawa, Satoshi Watanabe, Kazunori Maeda
  • Patent number: 6692883
    Abstract: A positive photoresist composition is disclosed, comprising a resin having a structural unit containing a specific group and capable of decomposing under the action of an acid to increase the solubility in an alkali developer, a resin having a structural unit containing a specific group and capable of decomposing under the action of an acid to increase the solubility in an alkali developer, and a compound capable of generating an acid upon irradiation with actinic rays or radiation.
    Type: Grant
    Filed: April 20, 2001
    Date of Patent: February 17, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Fumiyuki Nishiyama, Toru Fujimori, Shiro Tan
  • Patent number: 6692884
    Abstract: A positive photoresist composition comprises: a compound capable of generating an acid upon irradiation with an actinic ray or a radiation, in which the compound contains (A1) a sulfonate compound of a sulfonium, and (A2) a sulfonate compound of an N-hydroxyimide or a disulfonyldiazomethane compound; and a resin capable of decomposing by the action of an acid to increase the solubility in an alkali developing solution, in which the resin contains a repeating unit having a specific lactone structure.
    Type: Grant
    Filed: April 5, 2002
    Date of Patent: February 17, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toru Fujimori, Kunihiko Kodama, Kenichiro Sato, Toshiaki Aoai
  • Patent number: 6689530
    Abstract: A chemical amplification type resist composition contains as a photoacid generator a sulfonyldiazomethane compound of formula (1) wherein R is H or C1-4 alkyl or alkoxy, G is SO2 or CO, R3 is C1-10 alkyl or C6-14 aryl, p is 1 or 2, q is 0 or 1, p+q=2, n is 0 or 1, m is 3 to 11, and k is 0 to 4. The composition is suited for microfabrication, especially by deep UV lithography because of many advantages including improved resolution and improved pattern profile after development.
    Type: Grant
    Filed: September 27, 2002
    Date of Patent: February 10, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Katsuhiro Kobayashi, Kazunori Maeda
  • Patent number: 6677103
    Abstract: Disclosed is a novel chemical-amplification positive-working photoresist composition capable of giving a patterned resist layer with excellent properties such as photosensitivity, pattern resolution, heat resistance and cross sectional profile of the patterned resist layer. The composition is characterized by the use of, as the film-forming resinous component, a hydroxyl-containing resinous ingredient which is a combination of a first resin of which from 30 to 60% of the hydroxyl groups are substituted by acid-dissociable solubility-reducing groups and a second resin of which from 5 to 20% of the hydroxyl groups are substituted by acid-dissociable groups of the same kind as in the first resin in a weight proportion of 1.9 to 9:1.
    Type: Grant
    Filed: April 3, 2002
    Date of Patent: January 13, 2004
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazufumi Sato, Satoshi Maemori, Taku Nakao, Kazuyuki Nitta
  • Publication number: 20030235787
    Abstract: The present invention provides a composition and a method for forming a pattern on a substrate with the composition by forming a cross-linked polymer from the composition upon exposing the same to radiation. The viscosity and wetting properties of the composition are selected to facilitate formation of a layer from a plurality of spaced-apart beads of the material disposed on the substrate. To that end, in one embodiment of the present invention the composition includes a mono-functional acrylate component, a poly-functional molecule component, and an initiator component responsive to the radiation to initiate a free radical reaction to cause the mono-functional acrylate component and the poly-functional molecule component to polymerize and crosslink.
    Type: Application
    Filed: June 24, 2002
    Publication date: December 25, 2003
    Inventors: Michael P.C. Watts, Carlton Grant Willson, Todd Bailey, Stephen C. Johnson, Eui-Kyoon Kim, Nicholas A. Stacey
  • Publication number: 20030232270
    Abstract: The present invention discloses a chemical amplified photoresist composition including a polymer having a repeated unit of the formula (II), 1
    Type: Application
    Filed: May 28, 2002
    Publication date: December 18, 2003
    Applicant: Everlight USA, Inc.
    Inventors: Chi-Sheng Chen, Yen-Cheng Li, Meng-Hsum Cheng
  • Patent number: 6656660
    Abstract: A resist composition comprising (a) at least two kinds of polymers which become alkali-soluble by the action of an acid, (b) as a photoacid generator, a combination of an alkylsulfonyl diazomethane compound and a triarylsulfonium arylsulfonate compound or a diaryliodonium arylsulfonate compound, and (c) a solvent is excellent as a chemically amplified resist composition to give excellent pattern shape and very fine line-and-space, particularly when exposed to lights having a wavelength of 300 nm or less.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: December 2, 2003
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Fumiyoshi Urano, Hirotoshi Fujie, Naoki Takeyama, Koji Ichikawa
  • Patent number: 6653043
    Abstract: Active particles which when incorporated into a photosensitive composition containing base resin and diazonium-series photosensitizer provide improvement in at least one or both of sensitivity and resolutionn. The active particles include a particulate carrier, such as silica sol, and an aromatic unit directly or indirectly bonded to the carrier. The aromatic unit has a phenolic hydroxyl group and no substituent in at least one of the o- and p-positions, in relation to the phenolic hydroxyl group. The active particles, when incorporated into the photosensitive composition can, after exposure, increase solubility difference between the exposed and non-exposed areas.
    Type: Grant
    Filed: October 31, 2000
    Date of Patent: November 25, 2003
    Assignee: Kansai Research Institute, Inc.
    Inventor: Makoto Hanabata
  • Patent number: 6645698
    Abstract: The invention provides photoresist compositions comprising a resin binder having acid labile blocking groups requiring an activation energy in excess of 20 Kcal/mol. for deblocking, a photoacid generator capable of generating a halogenated sulfonic acid upon photolysis and optionally, a base additive. It has found that linewidth variation is substantially reduced when using the halogenated sulfonic aced generator in a process involving a high temperature post exposure bake.
    Type: Grant
    Filed: December 22, 1999
    Date of Patent: November 11, 2003
    Assignee: Shipley Company, L.L.C.
    Inventors: James W. Thackeray, James F. Cameron, Roger F. Sinta
  • Patent number: 6641984
    Abstract: In the method of frame plating according to the invention, a first patterned resist layer is formed using a first resist containing a material generating an acid; the first patterned resist layer is coated with a second resist capable of entering into a crosslinking reaction in the presence of an acid; an acid is generated in the first patterned resist layer to form a crosslinked film in a portion of the second resist near the boundary that touches the first patterned resist layer; and the non-crosslinked portion of the second resist is peeled off to form a second patterned resist layer, thereby forming a frame. As the first resist, a chemically amplifying type positive material containing a base resin comprising a high molecular compound shown by a predetermined formula and having a weight average molecular weight of 10000 to 25000 and a molecular weight distribution of as narrow as 1.05 to 1.25 is used.
    Type: Grant
    Filed: April 27, 2001
    Date of Patent: November 4, 2003
    Assignee: TDK Corporation
    Inventor: Akifumi Kamijima
  • Publication number: 20030203305
    Abstract: A negative resist composition comprising (A-1) an alkali-soluble resin containing a repeating unit represented by formula (1) defined in the specification, (A-2) an alkali-soluble resin containing a repeating unit represented by formula (2) defined in the specification, (B) a crosslinking agent crosslinking with the alkali-soluble resin (A-1) or (A-2) by the action of an acid, (C) a compound that generates an acid upon irradiation of an actinic ray or radiation, and (D) a nitrogen-containing basic compound.
    Type: Application
    Filed: March 26, 2003
    Publication date: October 30, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Shoichiro Yasunami, Yutaka Adegawa, Koji Shirakawa
  • Publication number: 20030198890
    Abstract: A negative-type planographic printing plate having, disposed on a support, a recording layer comprising an image recording material which contains an infrared ray absorbing agent and can be recorded by irradiation with an infrared ray, in which, as for the infrared ray absorbing agent comprising a cyanine dye, at least one of substituents on nitrogen atoms at both ends was selected from the group consisting of the following substituents: —C(═X)R1; —C(═X)NR2R3; —CH≡CR4R5; —C═CR6; —CHR7R8;—CR9R10R11; and —Ar, wherein X represents O, S or Se; R1 to R6 each independently represent H or a hydrocarbon group having 20 or fewer carbon atoms which may have a substituent; R7 to R11 each independently represent a hydrocarbon group having 20 or fewer carbon atoms which may have a substituent; and Ar represents an aromatic group which may have a substituent.
    Type: Application
    Filed: March 18, 2003
    Publication date: October 23, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Yukio Abe, Kazuto Shimada
  • Patent number: 6635400
    Abstract: A resist composition comprising (A) an alkali-insoluble or substantially insoluble polymer having acidic functional groups protected with acid labile groups, which polymer becomes alkali-soluble upon elimination of the acid labile groups, (B) a photoacid generator, and (C) a 1,2-naphthoquinonediazidosulfonyl group-bearing compound has a high resolution and sensitivity, and provides resist patterns of excellent plating resistance when used in UV lithography at an exposure light wavelength of at least 300 nm.
    Type: Grant
    Filed: April 17, 2001
    Date of Patent: October 21, 2003
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Hideto Kato, Kazuhiro Nishikawa, Yoshinori Hirano, Katsuya Takemura
  • Publication number: 20030194634
    Abstract: A novel anthracene derivative useful as an additive to a radiation-sensitive resin composition is disclosed.
    Type: Application
    Filed: March 6, 2003
    Publication date: October 16, 2003
    Inventors: Tomoki Nagai, Tsutomu Shimokawa
  • Publication number: 20030180653
    Abstract: A chemical amplification type resist composition contains as a photoacid generator a sulfonyldiazomethane compound of formula (1) wherein R is H or C1-4 alkyl or alkoxy, G is SO2 or CO, R3 is C1-10 alkyl or C6-14 aryl, p is 1 or 2, q is 0 or 1, p+q=2, n is 0 or 1, m is 3 to 11, and k is 0 to 4. The composition is suited for microfabrication, especially by deep UV lithography because of many advantages including improved resolution and improved pattern profile after development.
    Type: Application
    Filed: September 27, 2002
    Publication date: September 25, 2003
    Inventors: Youichi Ohsawa, Katsuhiro Kobayashi, Kazunori Maeda
  • Patent number: 6613844
    Abstract: A chemically amplified positive resist composition comprising a styrene polymer represented by formula (1), terminated with P, and having a weight average molecular wherein R is OH or OR3, R1 is H or CH3, R2 is alkyl, R3 is acid labile group, x≧0, y>0, k≧0, m≧0, n>0, 0<q≦0.8, p+q=1, P is H, alkyl, alkenyl, aromatic, carboxyl, OH, —R4(COR5)r, —R4O(OH)r or —R4 (OR5)r. A chemically amplified positive resist composition comprising the polymer as a base resin has high sensitivity and resolution and forms resist patterns having plasma etching resistance, heat resistance, and reproducibility.
    Type: Grant
    Filed: March 19, 2002
    Date of Patent: September 2, 2003
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Osamu Watanabe, Shimada Junji, Nagura Shigehiro, Takeda Takanobu
  • Publication number: 20030157423
    Abstract: 1.
    Type: Application
    Filed: December 18, 2002
    Publication date: August 21, 2003
    Inventors: Tomoki Nagai, Daisuke Shimizu, Tsutomu Shimokawa, Fumihisa Miyajima, Masaaki Miyaji
  • Publication number: 20030148206
    Abstract: A positive photosensitive composition containing (A) an acid generator capable of generating an acid by irradiation with actinic ray or radiation and having a structure represented by formula (I) defined in the specification and (B) a resin having a monocyclic or polycyclic alicyclic hydrocarbon structure and being decomposed by the action of an acid to increase solubility in an alkali developer.
    Type: Application
    Filed: October 2, 2002
    Publication date: August 7, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventor: Kunihiko Kodama
  • Publication number: 20030134221
    Abstract: A positive resist composition comprising a resin (A), which is decomposed by the action of an acid to increase solubility in an alkali developing solution, containing a structural unit including a group represented by formula (X) defined in the specification and/or a resin (B), which is decomposed by the action of an acid to increase solubility in an alkali developing solution, containing a structural unit including a group represented by formula (Y) defined in the specification, and a resin (C), which is decomposed by the action of an acid to increase solubility in an alkali developing solution, containing a structural unit including a group represented by formula (Q) defined in the specification; and a compound that generates an acid upon irradiation of an actinic ray or radiation.
    Type: Application
    Filed: November 1, 2002
    Publication date: July 17, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Fumiyuki Nishiyama, Toru Fujimori
  • Patent number: 6593056
    Abstract: A chemically amplified, positive resist composition comprising an organic solvent, a polymer having acid labile groups, a photoacid generator, a basic compound, and a compound containing at least two allyloxy groups is provided. The resist composition has a high sensitivity, resolution, dry etching resistance and process adaptability, and is improved in the slimming of a pattern film after development with an aqueous base solution. The resist composition is also applicable to the thermal flow process suited for forming a microsize contact hole pattern for the fabrication of VLSI.
    Type: Grant
    Filed: March 22, 2001
    Date of Patent: July 15, 2003
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takanobu Takeda, Jun Watanabe, Katsuya Takemura, Kenji Koizumi
  • Patent number: 6586152
    Abstract: The present invention relates to an agent for reducing substrate dependence useful as an ingredient of a resist composition used for preparation of semiconductor devices and the like, which comprises a compound shown by the following general formula [1]: wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1.
    Type: Grant
    Filed: June 12, 2000
    Date of Patent: July 1, 2003
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Fumiyoshi Urano, Naoki Katano, Tomoko Kiryu
  • Patent number: RE38254
    Abstract: Disclosed is an improved, chemically-amplifying positive resist composition for radiations, especially UV rays, deep-UV rays, excimer laser beams, X-rays, electron beams. The composition comprises (A) a resin component whose solubility in an alkaline aqueous solution is increased by the action of acids, (B) a chemical compound which generates an acid when exposed to radiations, and (C) an organic carboxylic acid compound and (D) an amine, in which said resin component (A) is a mixture comprising (a) a polyhydroxystyrene having a weight-average molecular weight of from 8,000 to 25,000 and a molecular weight distribution (Mw/Mn) of 1.
    Type: Grant
    Filed: September 20, 2001
    Date of Patent: September 16, 2003
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazufumi Sato, Kazuyuki Nitta, Akiyoshi Yamazaki, Yoshika Banba, Toshimasa Nakayama