Vinyl Alcohol Polymer Or Derivative Patents (Class 430/909)
  • Patent number: 6214521
    Abstract: A material for gravure recording by means of coherent electromagnetic radiation for letterpress printing, consisting of a substrate and a crosslinkable layer, with or without a release layer and/or cover sheet, the layer containing at least one ethylenically unsaturated compound, a polymerization initiator and at least one polymeric binder which consists of polyvinyl alcohol and/or at least one copolymer having a substantial proportion of the structural unit and containing a filler having a ceiling temperature of less than 800K, in particular less than 600K, e.g. polystyrene, polymethyl methacrylate, poly(ethylene)ketone, polyoxymethylene or poly(&agr;-methylstyrene), in particular having a spherical or roughly spherical form with a maximum dimension of about 5-10 &mgr;m. The material is very suitable for laser-engravable letterpress printing plates.
    Type: Grant
    Filed: August 24, 1999
    Date of Patent: April 10, 2001
    Assignee: BASF Drucksysteme GmbH
    Inventors: Thomas Telser, Uwe Stebani, Hartmut Sandig, Klaus-Dieter Tensierowski
  • Patent number: 6211328
    Abstract: The present invention relates to a phenol resin, in particular a phenol resin for resists suitable for forming resist patterns. The phenol resin of the present invention is obtained by reacting at least two components, i.e., a compound (A) such as 4-hydroxymethyl-2,6-dimethylphenol and a polymerizable phenol compound such as parahydroxystyrene or a polymer (B), which is a polymer of the polymerizable phenol compound, in a ratio of 1 to 50 moles of the compound (A) to 100 moles of the polymerizable phenol compound or 100 moles of structural unit of the polymerizable phenol compound contained in the polymer (B) in the presence of an acid and having a molecular weight of 2,000 to 20,000. Such a phenol resin provides good pattern shape, heat resistance, resolution, and sensitivity in resists for lithography.
    Type: Grant
    Filed: June 1, 2000
    Date of Patent: April 3, 2001
    Assignee: Gun Ei Chemical Industry Co., LTD
    Inventors: Yoshiaki Kurimoto, Katsuhiro Maruyama, Akira Yoshitomo, Satoru Yoshida, Satoru Kitano
  • Patent number: 6194120
    Abstract: Optical waveguides prepared by irradiating selected regions of positive photochromic polymeric materials with actinic radiation are disclosed. The photochromic materials undergo an irreversible photochemical change which results in an increase in the refractive index of light-exposed regions. In addition, the materials exhibit negligible second-order polarizability prior to exposure and excellent nonlinear optical properties after exposure and polarization. Thus, the exposed regions are particularly useful as the core in active waveguides for use in second-order nonlinear optical applications, as well as the core in passive waveguides. In addition, a simple two step process is disclosed for forming optical waveguides from the positive photochromic polymers. Optical structures, such as optical integrated circuits, and optical devices which incorporate the waveguides are also disclosed.
    Type: Grant
    Filed: May 5, 2000
    Date of Patent: February 27, 2001
    Assignee: Molecular OptoElectronics Corporation
    Inventors: Kwok Pong Chan, Brian L. Lawrence
  • Patent number: 6190829
    Abstract: A photoresist having both positive and negative tone components resulting in a lower “k” factor than the single tone photoresist is disclosed. The hybrid resist may either have the negative tone resist or the positive tone resist as the major portion, while the other tone is a relatively minor portion. For examples, a positive tone resist may include a minor portion of a negative tone cross-linker or a negative tone resist may include positively acting functional groups. The hybrid resist of the present invention allows for wider exposure dosage windows, therefore increasing the yield or performance and line density.
    Type: Grant
    Filed: September 16, 1996
    Date of Patent: February 20, 2001
    Assignee: International Business Machines Corporation
    Inventors: Steve J. Holmes, Ahmad D. Katnani, Niranjan M. Patel, Paul A. Rabidoux
  • Patent number: 6187510
    Abstract: A radiation sensitive plate structure and method for digitally producing a lithographic printing plate. The radiation sensitive plate structure comprises a substrate, a photosensitive layer which changes solubility in a developer liquid upon exposure to actinic radiation, and a photographic layer. The photographic layer comprises a silver halide emulsion dispersed in gelatin, a sensitizing dye, and an adhesion promoting component comprising a vinyl phenol copolymer and a polymeric keying agent. The method for digitally producing a lithographic printing plate comprises the following steps. The radiation sensitive plate structure is provided and the photographic layer is image-wise exposed to visible or laser radiation to form an exposed photographic layer. The exposed photographic layer is developed to form an opaque image mask.
    Type: Grant
    Filed: March 9, 1999
    Date of Patent: February 13, 2001
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Ken-Ichi Shimazu, Suck-Ju Hong
  • Patent number: 6168909
    Abstract: A material for forming a pattern according to the present invention is a chemically amplified resist, which contains a resin and an acid generator that generates an acid when exposed to exposing radiation. The resin includes a derivative of poly(vinyl alcohol), a derivative of a vinylamine polymer, a derivative of poly(N-hydroxyethylaziridine), a derivative of polyhydroxycyclohexene or a copolymer including at least one of these derivatives.
    Type: Grant
    Filed: September 9, 1999
    Date of Patent: January 2, 2001
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventor: Akiko Katsuyama
  • Patent number: 6153349
    Abstract: A photoresist composition comprising a resin having structural units represented by the following formulas (I), (II) and (III): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.11, R.sup.12, R.sup.13, R.sup.21, R.sup.22 and R.sup.23 each independently represents hydrogen or an alkyl; one of R.sup.14, R.sup.15 and R.sup.16 represents an aliphatic hydrocarbon residue and the rest each independently represents hydrogen or an aliphatic hydrocarbon residue, or two or three of R.sup.14, R.sup.15 and R.sup.16 form a hydrocarbon ring; and R represents a group cleavable by an action of an acid; and the photoresist composition affords excellent resolution, excellent profile and wide focus margin even on a substrate provided with an organic anti-reflective film.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: November 28, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Nobuhito Fukui, Koshiro Ochiai
  • Patent number: 6146811
    Abstract: Disclosed is photoresist using dioxaspiro ring-substitued acryl derivatives, represented by the following chemical formula I or II. As matrix polymers, homopolymers of dioxaspiro ring-substitued acryl monomers or their copolymers with acryl monomers are provided. The deprotection of the dioxaspiro rings from the matrix polymers, usually accomplished by the action of a photoacid generator, causes a great change in the water solubility of the matrix, thereby allowing the matrix to be used for the photoresist required to have high sensitivity, resolution and contrast.
    Type: Grant
    Filed: July 30, 1999
    Date of Patent: November 14, 2000
    Assignee: Korea Advanced Institute of Science and Technology
    Inventors: Jin Baek Kim, Jong Jin Park, Ji Hyun Jang
  • Patent number: 6140018
    Abstract: The invention provides a photosensitive resin and a photosensitive resin composition having excellent water resistance after hardening, excellent developability, and excellent patterning characteristics, and a pattern formation method making use of the composition. The invention provides saponified PVA photosensitive resin which contains structural units represented by formulas (I) and (II): ##STR1## the content of the structural units represented by formulas (I) and (II) in the resin being 0.5-10 mol % with respect to entirety of the structural units of the saponified product of PVA.
    Type: Grant
    Filed: August 5, 1999
    Date of Patent: October 31, 2000
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Noriaki Tochizawa, Mitsuharu Miyazaki, Takaho Ito
  • Patent number: 6087066
    Abstract: This invention relates to polyvinyl acetals containing the units A, B, C and D, whereinA is present in an amount of 0.5 to 20 wt.-% and is of the formula ##STR1## B is present in an amount of 15 to 35 wt.-% and is of the formula ##STR2## C is present in an amount of 10 to 50 wt.-% and is of the formula ##STR3## wherein R.sup.1 is an alkyl group with up to 4 carbons, which is optionally substituted by an acid group, or a phenyl group, to which an acid group is attached, wherein the phenyl group optionally comprises 1 to 2 further substituents selected from halos, amino, methoxy, ethoxy, methyl and ethyl groups, or is a group X--NR.sup.6 --CO--Y--COOH, wherein X is an aliphatic, aromatic or araliphatic spacer group, R.sup.6 is hydrogen or an aliphatic, aromatic or araliphatic moiety and Y is a saturated or unsaturated chain- or ring-shaped spacer group, and this unit C may be contained several times with various moieties R.sup.1 independent of one another, and D is present in an amount of 25 to 70 wt.
    Type: Grant
    Filed: October 14, 1999
    Date of Patent: July 11, 2000
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Harald Baumann, Celin Savariar-Hauck, Hans-Joachim Timpe
  • Patent number: 6066432
    Abstract: A silver halide light-sensitive material comprises a support, a hardening layer and a light-sensitive layer in order. The light-sensitive layer contains silver halide and a hydrophilic polymer. The hardening layer or the light-sensitive layer contains a reducing agent. The hardening layer contains a mixture of a polymer (A) and a polymer (B). The mixture contains the polymer (A) in an amount of 5 to 70 wt. % and the polymer (B) in an amount of 30 to 95 wt. %. The polymer (A) comprises repeating units of (A1) in an amount of not less than 95 mol %. The polymer (B) comprises repeating units of (B1) in an amount of 10 to 90 mol % and repeating units of (B2) in an amount of 10 to 90 mol %.
    Type: Grant
    Filed: June 16, 1999
    Date of Patent: May 23, 2000
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Hiromitsu Yanaka
  • Patent number: 6048661
    Abstract: Provided are polymeric compounds which, when used as base resins in resist materials, can yield chemical resist materials having high sensitivity, high resolution, a high exposure latitude, and good process adaptability, exhibiting excellent resistance to plasma etching, and giving resist patterns having high thermal resistance, as well as chemically amplified positive type resist materials using such polymeric compounds as base resins. These chemically amplified positive type resist materials use a base resin comprising a polymeric compound having a weight-average molecular weight of 1,000 to 500,000 and having one or more hydroxyl and/or carboxyl groups in the molecule, part or all of the hydrogen atoms of the hydroxyl and/or carboxyl groups being replaced by groups of the following general formula ##STR1## and additionally contain an acid generator, a dissolution inhibitor, a basic compound, and an aromatic compound having a group of the formula .tbd.C--COOH.
    Type: Grant
    Filed: March 2, 1998
    Date of Patent: April 11, 2000
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Jun Hatakeyama, Shigehiro Nagura, Toshinobu Ishihara
  • Patent number: 6037097
    Abstract: The present invention relates to chemically amplified resists and resist systems wherein some of the polar functional groups of the aqueous base soluble polymer or copolymers are protected with a cyclic aliphatic ketal protecting group such as methoxycyclohexanyl. The resists and the resist systems of the present invention containing the new protecting group have improved shelf-life and vacuum stability as compared to the prior art resists. Thus, the resists of the present invention are highly useful in e-beam lithographic applications.
    Type: Grant
    Filed: January 27, 1998
    Date of Patent: March 14, 2000
    Assignee: International Business Machines Corporation
    Inventors: James J. Bucchignano, Wu-Song Huang, Ahmad D. Katnani, Kim Y. Lee, Wayne M. Moreau, Karen E. Petrillo
  • Patent number: 5994025
    Abstract: There is provided a photoresist including (a) a resin composed of a polymer represented with the following general formula [1], and (b) a photo acid generator which produces acid when exposed to a light: ##STR1## wherein each of R.sup.1, R.sup.3 and R.sup.7 represents one of a hydrogen atom and a methyl group, R.sup.2 represents a hydrocarbon group including a bridged cyclic hydrocarbon group and having a carbon number in the range of 7 to 13 both inclusive, R.sup.4 represents one of a hydrogen atom and a hydrocarbon group having a carbon number of 1 or 2, R.sup.5 represents a hydrocarbon group having a carbon number of 1 or 2, R.sup.
    Type: Grant
    Filed: December 10, 1996
    Date of Patent: November 30, 1999
    Assignee: NEC Corporation
    Inventors: Shigeyuki Iwasa, Kaichiro Nakano, Katsumi Maeda, Takeshi Ohfuji, Etsuo Hasegawa
  • Patent number: 5948591
    Abstract: According to the present invention there is provided a heat sensitive imaging element comprising a lithographic base with a hydrophilic surface, an image forming layer including a hydrophobic thermoplastic polymer latex and a compound capable of converting light into heat being present in said image forming layer or a layer adjacent thereto, characterized in that the image forming layer includes an alkali soluble copolymer containing acetal groups and hydroxy groups which have at least partially reacted with a compound with at least two carboxyl groups.
    Type: Grant
    Filed: May 6, 1998
    Date of Patent: September 7, 1999
    Assignee: Agfa-Gevaert, N.V.
    Inventors: Joan Vermeersch, Marc Van Damme
  • Patent number: 5925491
    Abstract: Polymeric binders for photosensitive compositions exhibiting improved ink acceptance, good developability and wetting, high photosensitivity, good image resolution, and larger printing runs for plates employing such photosensitive compositions.
    Type: Grant
    Filed: January 9, 1997
    Date of Patent: July 20, 1999
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Harald Baumann, Udo Dwars, Celin Savariar-Hauck, Hans-Joachim Timpe
  • Patent number: 5922507
    Abstract: The present invention provides a photosensitive imaging element comprising on a support a two-phase layer, said two-phase layer comprising a disperse hydrophobic photopolymerizable. phase and a hydrophilic continuous phase, characterized in that the hydrophobic photopolymerizable phase comprises a multifunctional monomer with a perfluoroalkyl or perfluoroalkenyl group.
    Type: Grant
    Filed: February 25, 1997
    Date of Patent: July 13, 1999
    Assignee: AGFA-Gevaert, N.V.
    Inventors: Marc Van Damme, Joan Vermeersch, Wolfgang Podszun, Norbert Lui
  • Patent number: 5910392
    Abstract: The present invention discloses a chemically amplified resist composition that is able to form a resist pattern that can be exposed in short wavelength regions, has good transparency, sensitivity, dry-etch resistance and resolution, while also exhibiting excellent adhesion to the substrate. This chemically amplified resist composition comprises: the combination of a base resin comprised of a polymer that is itself insoluble in a basic aqueous solution and contains at least (A) a monomer unit I having carboxylic acid or phenol protected with a specific protective group, and (B) a monomer unit II having an ester group or ether group that contains a cyclic carbonate structure, and can become soluble in a basic aqueous solution when the protective group of the monomer unit I is deprotected by the effect of the acid; and, a photo acid generator capable of generating an acid that can provoke deprotection of the protective group of monomer unit I when decomposed by absorption of imaging radiation.
    Type: Grant
    Filed: June 26, 1997
    Date of Patent: June 8, 1999
    Assignee: Fujitsu Limited
    Inventors: Koji Nozaki, Ei Yano, Keiji Watanabe, Takahisa Namiki, Miwa Igarashi
  • Patent number: 5851731
    Abstract: A water processable photopolymeric composition for use in the manufacture of flexographic photopolymer printing plates is disclosed. Preferably, the flexomer blend includes a flexomer having an affinity for water combined with a hydrophilic crosslinking agent, a nonhydrophilic crosslinking agent, a swell enhancing filler, a hydrophilic plasticizer, a compatibilizer and a surfactant. The compatibilizer aids the blending of the hydrophilic components with the flexomer blend.
    Type: Grant
    Filed: September 9, 1996
    Date of Patent: December 22, 1998
    Assignee: M. A. Hanna Company
    Inventors: Carl David McAfee, Piseth Lov, David Thomas Hughes, Michael Wayne Chase
  • Patent number: 5830623
    Abstract: It is an object of the present invention to obtain a resist pattern of a high dimensional accuracy. In order to accomplish this object, a pattern lithography method according to the present invention comprises the steps of: forming a resist film 2 on a substrate 1 to be processed; applying a hydrous polymer solution 4 on the resist film 2; cross-linking polymers in the hydrous polymer solution to form a hydrogel film 4a of a predetermined thickness; and pattern-exposing the resist film 2 through the hydrogel film, and then, removing the hydrogel film 4a.
    Type: Grant
    Filed: September 12, 1996
    Date of Patent: November 3, 1998
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Yumiko Maruyama, Takahiro Ikeda
  • Patent number: 5814431
    Abstract: A photosensitive composition comprising(a) a resin selected from the group consisting of novolak resins and polyvinylphenol resins;(b) an amino compound derivative capable of curing the resin;(c) at least one member selected from the group consisting of cyanine compounds of the following formula (I) and polymethine compounds of the following formula (II), as a compound showing absorption in a near infrared wavelength region: ##STR1## (d) a photosensitive acid-forming agent.
    Type: Grant
    Filed: January 6, 1997
    Date of Patent: September 29, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hideki Nagasaka, Akihisa Murata, Toshiyuki Urano, Ryuichiro Takasaki
  • Patent number: 5773191
    Abstract: A radiation-sensitive composition is disclosed which includes:(a) a copolymer represented by the general formula: ##STR1## wherein R.sup.1 is a hydrogen atom or a methyl group, R.sup.2 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, Ar is a substituted or unsubstituted phenylene group or a substituted or unsubstituted cyclohexylene group, X is a divalent group represented by --SO.sub.2 -- or --CO--, m and n are individually an integer not less than 1;(b) a dissolution inhibitor composed of a compound represented by the general formula: ##STR2## wherein R.sup.3 is an alkyl group or a substituted or unsubstituted aryl group, R.sup.4 is an alkylene group, a cycloalkylene group, an alkenylene group or an alkynylene group, R.sup.
    Type: Grant
    Filed: July 24, 1996
    Date of Patent: June 30, 1998
    Assignee: Hoechst Japan Limited
    Inventors: Munirathna Padmanaban, Yoshiaki Kinoshita, Satoru Funato, Natsumi Kawasaki, Hiroshi Okazaki, Georg Pawlowski
  • Patent number: 5759750
    Abstract: A radiation-sensitive mixture essentially consisting of(a) a water-insoluble binder or binder mixture and(b) a compound which forms a strong acid on exposure to radiation,component (a) being a phenolic resin in which some or all of the phenolic hydroxyl groups have been replaced with groups (IA) or (IB) ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each alkyl or R.sup.1 together with R.sup.2 forms a ring and X is CH.sub.2, O, S, SO.sub.2 or NR.sup.4, is suitable for the production of relief structures.
    Type: Grant
    Filed: April 18, 1997
    Date of Patent: June 2, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Binder, Reinhold Schwalm, Dirk Funhoff
  • Patent number: 5750313
    Abstract: Disclosed are a photosensitive resin composition essentially comprising 100 parts by weight of modified polyvinyl alcohol comprising a structural units of formulae (I), (II) and (III): ##STR1## wherein R represents a hydrocarbon group having 1 to 20 carbon atoms; X represents an aliphatic, alicyclic or aromatic divalent hydrocarbon group having 1 to 20 carbon atoms or a divalent group having at least one carboxyl group in the molecule thereof, the proportion of the structural unit of formula (I) being from 1 to 40 mol %, the total proportion of the structural units of formulae (II) and (III) being from 60 to 99 mol %, and the carboxyl equivalent attributed to the structural unit of formula (III) being from 0.3 to 5 mol/kg, (B) from 0.1 to 10 parts by weight of an unsaturated epoxy compound, (C) from 20 to 200 parts by weight of a polymerizable unsaturated compound having an ethylenical double bond in the molecule thereof, and (D) from 0.1 to 10 parts by weight of a photopolymerization initiator.
    Type: Grant
    Filed: January 13, 1997
    Date of Patent: May 12, 1998
    Assignee: Toray Industries, Inc.
    Inventors: Hiroshi Tamada, Shigetora Kashio, Tamio Adachi
  • Patent number: 5723258
    Abstract: There are provided acetal group-containing alkoxy-styrene polymers represented by the following formula I: ##STR1## wherein R.sub.1 and R.sub.3 may be the same or different, and represent a hydrogen atom or a methylene group; R.sub.2 represents ##STR2## wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 may be the same or different, and independently represent a hydrogen atom, an alkyl group or an aryl group; m+n=1; k is an integer of 1-5; and l is an integer of 0-5; and an acid-generating agent, and chemical amplified negative photoresist composition comprising the same. It shows excellent transparency and sensitivity to deep UV in addition to being resistant to dry etching and alkali-developable.
    Type: Grant
    Filed: March 3, 1997
    Date of Patent: March 3, 1998
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Ji-Hong Kim, Sun-Yi Park, Seong-Ju Kim, Joo-Hyeon Park
  • Patent number: 5707777
    Abstract: A positive-working light-sensitive composition which comprises:(a) 0.5 to 80% by weight of a compound which has at least one group capable of being decomposed by an acid and whose solubility in an alkaline developer is increased by an acid;(b) 0.01 to 20% by weight of a disulfone compound represented by the following formula (I);R.sup.1 --SO.sub.2 --SO.sub.2 --R.sup.2 (I)wherein R.sup.1 and R.sup.2 may be the same or different and represent a substituted or unsubstituted alkyl, alkenyl or aryl group; and(c) 5 to 99.49% by weight of a resin insoluble in water and soluble in an alkaline water,wherein the compound of the component (a) has a molecular weight of not more than 2,000 and a boiling point of not less than 150.degree. C. and wherein a film of the composition having a thickness of 1 .mu.m has an optical density determined at 248 nm of not more than 1.4 before exposure to light and the optical density of the composition determined at 248 nm is reduced by exposure to light of 248 nm.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: January 13, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Tadayoshi Kokubo
  • Patent number: 5700624
    Abstract: The invention comprises an acid hardened resist system consisting of a resin binder having acid labile blocking groups and inert blocking groups and a photoacid generator. The inclusion of inert blocking groups on the resin improves shelf life without deleteriously affecting photolithographic properties of the resist.
    Type: Grant
    Filed: May 9, 1995
    Date of Patent: December 23, 1997
    Assignee: Shipley Company, L.L.C.
    Inventors: James W. Thackeray, Roger F. Sinta, Mark D. Denison, Sheri L. Ablaza
  • Patent number: 5691101
    Abstract: Disclosed are a safe slurry photosensitive composition superior in image formation capabilities such as resolution and sensitivity and containing no harmful compound, and a safe water-soluble photosensitive composition capable of being dissolved in water without using any organic solvent while maintaining a sufficient sensitivity as a resist and containing no harmful substance. The slurry photosensitive composition contains a compound which generates an acid when irradiated with light or ionizing radiation, at least one type of a resin with acid-crosslinkability or acid-decomposability, and a powder. Various devices can be manufactured by forming a layer of this photosensitive composition on a substrate, exposing the layer to light in accordance with a desired pattern, and heating the layer. The water-soluble photosensitive composition contains a compound which generates an acid when irradiated with light or ionizing radiation, and an acetal resin.
    Type: Grant
    Filed: May 9, 1996
    Date of Patent: November 25, 1997
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Toru Ushirogouchi, Naomi Shida, Takuya Naito, Koji Asakawa, Akinori Hongu, Makoto Nakase, Hirokazu Niki
  • Patent number: 5679495
    Abstract: A radiation sensitive resin composition which comprises (A) a polymer which becomes alkali-soluble in the presence of an acid and (B) a radiation sensitive acid generator which generates an acid upon irradiation with a radiation, said polymer (A) comprising two recurring units represented by the general formulas (1) and (2) and a recurring unit which acts to reduce the solubility of the polymer in an alkali developer after the irradiation: ##STR1## wherein R.sup.1 represents a hydrogen atom or a methyl group and R.sup.2 represents a hydrogen atom or a methyl group. Said composition provides a chemically amplified positive resist which can give a fine pattern with a good pattern shape, and said resist is freed from volume shrinkage, peeling failure and adhesive failure, is excellent in dry etching resistance and effectively reacts with various radiations to give a good pattern shape which is excellent in photolithographic process stability, said pattern shape having no thinned portion at the upper part.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: October 21, 1997
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Mikio Yamachika, Eiichi Kobayashi, Toshiyuki Ota, Akira Tsuji
  • Patent number: 5670299
    Abstract: A resist composition comprising (a) a polymer having at least repeating units of the formulae: ##STR1## (b) a photoacid generator and (c) a solvent, has high sensitivity to light, excellent heat resistance, adhesiveness to a substrate and suitable for pattern formation with high resolution.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 23, 1997
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Fumiyoshi Urano, Hirotoshi Fujie, Keiji Oono, Takaaki Negishi
  • Patent number: 5627011
    Abstract: The invention relates to the use of oxime sulfonates of formula 1 ##STR1## wherein R is naphthyl, ##STR2## Ar is an unsubstituted aryl group or an aryl group which carries one or more than one substituent selected from the group consisting of nitro, chloro, bromo, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 perfluoroalkyl, C.sub.1 -C.sub.4 alkoxy and acid degradable substituents;R.sub.0 is either a R.sub.1 --X group or R.sub.2 ;X is an oxygen or a sulfur atom;R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or unsubstituted phenyl or phenyl which is substituted by a member selected from the group consisting of chloro, bromo, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkoxy, andR.sub.2 is hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: May 6, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Norbert Munzel, Reinhard Schulz, Heinz Holzwarth, Stephan Ilg
  • Patent number: 5601965
    Abstract: An aqueous-developable dry-film photopolymerizable composition is disclosed wherein the photopolymerizable composition contains a hydroxyl-modified vinyl chloride/vinyl acetate polymer.
    Type: Grant
    Filed: May 20, 1996
    Date of Patent: February 11, 1997
    Assignee: MacDermid Imaging Technology, Inc.
    Inventor: Richard T. Mayes
  • Patent number: 5558971
    Abstract: A resist material comprising (a) a terpolymer, (b) a photoacid generator, and (c) a solvent has high light sensitivity, heat resistance, adhesiveness, resolution, etc., and is suitable for forming a pattern of rectangular shape.
    Type: Grant
    Filed: March 21, 1995
    Date of Patent: September 24, 1996
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Takaai Negishi, Akiko Katsuyama, Masayuki Endo
  • Patent number: 5558976
    Abstract: A resist material comprising (a) a terpolymer, (b) a photoacid generator, and (c) a solvent has high light sensitivity, heat resistance, adhesiveness, resolution, etc., and is suitable for forming a pattern of rectangular shape.
    Type: Grant
    Filed: November 29, 1995
    Date of Patent: September 24, 1996
    Assignees: Wako Pure Chemical Industries, LTD., Matsushita Electric Industrial Co., LTD.
    Inventors: Fumiyoshi Urano, Takaaki Negishi, Akiko Katsuyama, Masayuki Endo
  • Patent number: 5547812
    Abstract: Microbridge formation in chemically amplified negative tone photoresists based on poly(hydroxystyrene) (PHS) is avoided when the PHS is blended together with a co-polymer of PHS and an acrylic polymer such as poly(methyl methacrylate) (PMMA). The blend should include at least 10% by weight of the co-polymer. In operation, hydrogen bonding between the hydroxystyrene sub-units and the methacrylate sub-units decreases the availability of sites for crosslinking, and this reduction in crosslinking sites makes the blend less susceptible to formation of polymer resist microbridges. The invention is practicable with a polymers having a wide range of molecular weights (2000-50000 daltons), and development can be achieved using the industry standard 2.38 wt % trimethylammonium hydroxide (TMAH) developer without any adverse impact on the photoresist.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 20, 1996
    Assignee: International Business Machines Corporation
    Inventors: James P. Collins, Judy Dorn, James T. Fahey, Leo Linehan, William J. Miller, Wayne Moreau, Erik A. Puttlitz, Randolph Smith, Gary Spinillo
  • Patent number: 5474872
    Abstract: A new photoresist composition suited for fine processing is provided which has practical applications in various dry etching processes. An advantageous pattern formation method using such a photo-resistive composition is also provided. The photoresist composition includes a substance containing a skeleton as at least a part of a main chain. The skeleton is obtained through polymerization of a vinyl alcohol type compound such as a polyvinyl alcohol chain, at least some hydroxyl groups in the skeleton being protected by acid-releasing protective groups. The skeleton preferably contains a group for improving the dry etching resistance. The photoresist composition also includes an optical acid generator. Development with a high polarity solvent, for instance aqueous development, is provided. A positive pattern is obtained by aqueous development, and a negative pattern is obtained by alcohol development.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: December 12, 1995
    Assignee: Sony Corporation
    Inventors: Yoichi Tomo, Masao Saito
  • Patent number: 5470662
    Abstract: Holographic films contain a copolymer binder having the following formula:(M).sub.w (VAc).sub.x (VOH).sub.y (CTFE).sub.zwherein M is a fluoromonomer; VAc is vinyl acetate; VOH is vinyl alcohol; and CTFE is chlorotrifluoroethylene; and wherein w, x, y, and z are percentages by weight; w is 5 to 22%, x is 50 to 75%, y is 3 to 8%, and z is 15 to 30% with the copolymer containing 3-35% by weight fluorine. These imaged films are particularly suited for lamination to glass in head-up display applications.
    Type: Grant
    Filed: October 25, 1994
    Date of Patent: November 28, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Andrew M. Weber, Aleksander Beresniewicz
  • Patent number: 5468589
    Abstract: A resist composition comprising (a) a polymer having at least repeating units of the formulae: ##STR1## (b) a photoacid generator and (c) a solvent, has high sensitivity to light, excellent heat resistance, adhesiveness to a substrate and suitable for pattern formation with high resolution.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: November 21, 1995
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Hirotoshi Fujie, Keiji Oono, Takaaki Negishi
  • Patent number: 5462840
    Abstract: A compound, method of manufacture and method for use of an alternating copolymer having the structure ##STR1## wherein X is independently H, C.sub.1 to C.sub.10 alkyl or alkoxy, primary or secondary amino or halogen, and R is aliphatic, cycloaliphatic, or aliphatic heterocyclic, and wherein the molecular weight ranges from about 1,000 to 50,000.
    Type: Grant
    Filed: March 19, 1991
    Date of Patent: October 31, 1995
    Assignee: Hoechst Celanese Corporation
    Inventor: Richard Vicari
  • Patent number: 5455154
    Abstract: A photographic silver halide material which has at least one light-sensitive layer and contains in at least one layer a compound corresponding to formula (I) in a quantity of at least 10 mg/m.sup.2 : ##STR1## wherein k stands for 50 to 99% by weight,l stands for 0 to 49% by weight,m stands for 1 to 40% by weight,j stands for 0 to 49% by weight,M denotes a comonomer incorporated by polymerisation,M.sub.1 denotes ##STR2## M.sub.2 denotes ##STR3## R.sub.1 and R.sub.2 denote hydrogen or alkyl, R.sub.3 denotes an acidic group, andB denotes a chemical bond or a bridging member and which is hardened with a rapid or an instant hardener,is distinguished by improved wet scratch resistance and stability in storage.
    Type: Grant
    Filed: May 23, 1994
    Date of Patent: October 3, 1995
    Assignee: Agfa Gevaert, AG
    Inventors: Gunter Helling, Jean-Marie Dewanckele
  • Patent number: 5445916
    Abstract: Photopolymers based on polyvinyl alcohol derivatives of 8-hydroxy quinoline compositions having a high degree of photosensitivity, a marked degree of water solubility, and the ability to photodimerize when exposed to actinic radiation.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: August 29, 1995
    Assignee: Ulano Corporation
    Inventor: John Curtis
  • Patent number: 5441797
    Abstract: A process is disclosed for making circuit elements by photolithography comprising depositing an antireflective polyimide or polyimide precursor layer on a substrate and heating the substrate at 200.degree. C. to 500.degree. C. to provide a functional integrated circuit element that includes an antireflective polyimide layer. The antireflective polyimide layer contains a sufficient concentration of at least one chromophore to give rise to an absorbance sufficient to attenuate actinic radiation at 405 or 436 nm. Preferred chromophores include those arising from perylenes, naphthalenes and anthraquinones. The chromophore may reside in a dye which is a component of the polyimide coating mixture or it may reside in a residue which is incorporated into the polyimide itself.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: August 15, 1995
    Assignee: International Business Machines Corporation
    Inventors: Dennis P. Hogan, Harold G. Linde, Ronald A. Warren
  • Patent number: 5427890
    Abstract: A method for engraving and/or etching comprising the steps of: (a) a process for exposing, to light, a layer of a water-soluble resin composition of a laminated photosensitive film which comprises a supporting sheet, a image mask-protection layer peelablly adhered to the supporting sheet and a layer of a water-soluble resin composition having photocrosslinkability to thus cause crosslinking of the exposed area of the resin layer to thereby form a predetermined pattern on the resin layer; (b) a process for dissolving out the non-crosslinked portion of the layer of the water-soluble photo-sensitive resin composition by developing the layer with water to thus from an image-carrying mask which is constituted from the crosslinked area of the photo-sensitive resin composition remaining on the image mask-protection layer; (c) a process for adhering the photo-sensitive laminate film on which the images are formed to the surface of a material to be processed; (d) a process for peeling off the supporting sheet from the
    Type: Grant
    Filed: September 3, 1993
    Date of Patent: June 27, 1995
    Assignee: Aicello Chemical Co., Ltd.
    Inventors: Tsutomu Suzuki, Ikuo Suzuki
  • Patent number: 5415971
    Abstract: A photosensitive mask laminate having a photoimageable, pressure sensitive adhesive layer and a photoimageable masking layer is disclosed. The laminate also includes a support layer, and it can include a removable carrier layer and a release layer. The laminate can be imaged by selective exposure to light or other radiation, and developing the laminate produces a mask having void and mask areas. The mask can then be used to protect selected portions of a target surface during a sandblast decorative process.
    Type: Grant
    Filed: April 2, 1993
    Date of Patent: May 16, 1995
    Assignee: The Chromaline Corporation
    Inventors: Ron Couture, Todd R. Murphy, Toshifumi Komatsu
  • Patent number: 5413863
    Abstract: Holographic films are disclosed that contain a binder having the following formula:(M).sub.w (VAc).sub.x (VOH).sub.y (VOS).sub.zwherein M is a fluoromonomer; VAc is vinyl acetate; VOH is vinyl alcohol; and VOS is vinyl trimethylsilyl ether; and wherein w, x, y, and z are percentages by weight; w is 5 to 30, x is 40 to 80, y is 0 to 20, and z is 2 to 30; said copolymers containing 3 to 23% by weight fluorine. These imaged films are particularly suited for lamination to glass in head-up display applications.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: May 9, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Andrew M. Weber, Aleksander Beresniewicz
  • Patent number: 5409801
    Abstract: A method for improving the resolution of an electron resist pattern on a substrate coated with a polymeric electron resist film is disclosed which provides an external coating layer of dried polymer selected from the group consisting of water-soluble polymers and poly(m-phenylene isophthalamide), or of a mixture consisting essentially of said dried polymer and hexavalent tungsten compounds wherein the weight ratio of the tungsten compounds to polymer is up to about 1:1. Also disclosed are substrates coated with a polymeric resist film wherein the resist film consists essentially of such external layers, or wherein an external coating layer of said polymer-tungsten compound mixture is provided.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: April 25, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Robert V. Kasowski, Sau L. Tang
  • Patent number: 5397679
    Abstract: This invention provides a process for producing a cyclic carbonate compound represented by the following formula (5): ##STR1## or the like which is useful as a dissolution inhibitor for use in a chemically amplified positive photoresist, as well as a positive photoresist composition comprising said cyclic carbonate compound, an alkali-soluble resin and a photo-induced acid precursor. This composition gives a positive photoresist excellent in performances such as resolution, profile, sensitivity, etc.
    Type: Grant
    Filed: April 9, 1993
    Date of Patent: March 14, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuji Ueda, Naoki Takeyama, Hiromi Ueki, Takehiro Kusumoto
  • Patent number: 5385809
    Abstract: A process for enhancing the performance of resist polymers in lithographic processes for device fabrication is disclosed. The resist polymers contain acid labile functional groups. When these functional groups are removed and replaced by hydrogen, the polymer becomes more soluble in the aqueous base developer solutions used in lithographic processes. A portion of the acid-labile functional groups are cleaved from the polymer to obtain a resist polymer with increased sensitivity, improved adhesion, and reduced film shrinkage during post-exposure bake. The acid labile functional groups are cleaved by dissolving the polymer in a suitable solvent and subjecting the mixture to increased temperature until the desired number of acid labile functional groups are cleaved from the polymer. The polymer is then recovered from the mixture and employed as a resist in a lithographic process for device fabrication.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: January 31, 1995
    Assignee: AT&T Corp.
    Inventors: Michael P. Bohrer, David A. Mixon
  • Patent number: 5368993
    Abstract: The present invention relates to photoresists particularly suitable for deep U.V. exposure and having the capability of forming highly resolved features. The invention is characterized by use of a resist resin binder that comprises a nonaromatic cyclic alcohol-phenol copolymer that has a relatively low molecular weight and narrow distribution of molecular weight and cyclic alcohol concentration.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: November 29, 1994
    Assignee: Shipley Company Inc.
    Inventors: James W. Thackeray, Mark Denison, George W. Orsula
  • Patent number: 5366842
    Abstract: The invention creates a selective oxygen barrier around individual coupler or other photographically active particles by surrounding each particle with a layer of water applicable oxygen barrier polymer such as polyvinyl alcohol (PVA), which will also act as a steric barrier to coalescence of the particles. Photographic products formed with such materials are more dye stable.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: November 22, 1994
    Assignee: Eastman Kodak Company
    Inventors: Pranab Bagchi, James L. Edwards, Wendell F. Smith, Jr., Brian Thomas