Quinone Diazide Containing Patents (Class 430/189)
  • Patent number: 11137682
    Abstract: The present invention relates to a photosensitive resin composition that is excellent in adhesiveness and sensitivity. Specifically, the photosensitive resin composition is capable of providing a cured film that is excellent in transparency, sensitivity, chemical resistance, and adhesiveness upon immersion in a stripper. Thus, the cured film can be effectively used in a liquid crystal display, an organic EL display, and the like.
    Type: Grant
    Filed: October 15, 2018
    Date of Patent: October 5, 2021
    Inventors: Kahee Shin, Jong Han Yang, Geun Huh
  • Patent number: 8993214
    Abstract: A positive photosensitive siloxane composition comprising at least three types of following polysiloxanes (A), (B) and (C) obtained by hydrolyzing and condensing a silane compound represented by general formula (1) R1nSi (OR2)4-n, a diazonaphthoquinone derivative, and a solvent: a polysiloxane (A) such that if pre-baked the film thereof will be soluble in a 5 weight % TMAH aqueous solution and the solution rate of said film will be 1,000 ?/sec or less; a polysiloxane (B) such that if pre-baked the solution rate of the film thereof will be 4,000 ?/sec or more relative to a 2.38 weight % TMAH aqueous solution; and a polysiloxane (C) such that if pre-baked the solution rate of the film thereof will be between 200 and 3,000 ?/sec relative to a 2.38 weight % TMAH aqueous solution.
    Type: Grant
    Filed: May 15, 2012
    Date of Patent: March 31, 2015
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Daishi Yokoyama, Takashi Fuke, Yuji Tashiro, Takashi Sekito, Toshiaki Nonaka
  • Patent number: 8883397
    Abstract: A positive photosensitive siloxane composition containing: a polysiloxane (Ia), which is obtained by hydrolyzing and condensing the silane compound represented by RSi(OR1)3 in general formula (1) and the silane compound represented by Si(OR1)4 in general formula (2) in the presence of a basic catalyst, and a pre-baked film of which has a dissolution rate of 1,000 ?/second or less in a 5 wt % TMAH aqueous solution; a polysiloxane (Ib), which is obtained by hydrolyzing and condensing at least the silane compound represented by general formula (1) in the presence of an acid or basic catalyst, and a pre-baked film of which has a dissolution rate of 100 ?/second or more in a 2.38 wt % TMAH aqueous solution; and a diazonaphthoquinone derivative and solvent.
    Type: Grant
    Filed: August 19, 2011
    Date of Patent: November 11, 2014
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Daishi Yokoyama, Takashi Fuke, Yuji Tashiro, Takashi Sekito, Toshiaki Nonaka
  • Patent number: 8828640
    Abstract: This invention relates to a photo-curing polysiloxane composition including a polysiloxane, a quinonediazidesulfonic acid ester, a methylene alkoxyaryl-containing compound as a curing agent, and a solvent for dispersing the polysiloxane, the quinonediazidesulfonic acid ester, and the methylene alkoxyaryl-containing compound. This invention also provides a protecting film made from the photo-curing polysiloxane composition, and an element containing the protecting film.
    Type: Grant
    Filed: November 7, 2012
    Date of Patent: September 9, 2014
    Assignee: Chi Mei Corporation
    Inventors: Ming-Ju Wu, Chun-An Shih
  • Patent number: 8722311
    Abstract: There is provided a resist composition suitable for forming a microlens which is excellent in transparency, heat resistance, and sensitivity characteristics, excellent in solubility in a developer, and as the result thereof has high resolution. A positive resist composition comprising; a component (A): an alkali-soluble polymer; a component (B): a compound having an organic group to be photolyzed to generate an alkali-soluble group; a component (C): a crosslinkable compound of Formula (1): [where R1, R2, and, R3 are independently a C1-6 alkylene group or oxyalkylene group which are optionally branched; and E1, E2, and E3 are independently a group containing a structure of Formula (2) or Formula (3): (where R4 is a hydrogen atom or a methyl group)]; and a component (D): a solvent.
    Type: Grant
    Filed: January 19, 2011
    Date of Patent: May 13, 2014
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Shojiro Yukawa, Shinya Arase, Toshiaki Takeyama, Yuki Endo, Takeo Moro
  • Patent number: 8133550
    Abstract: A polybenzoxazole precursor is represented by the following formula (1): wherein R1a to R4a, R1b to R4b, X1, Y1 and m are defined in the specification.
    Type: Grant
    Filed: September 14, 2007
    Date of Patent: March 13, 2012
    Assignee: FUJIFILM Corporation
    Inventors: Kenichiro Sato, Tsukasa Yamanaka
  • Patent number: 7670745
    Abstract: The invention provides an alkali soluble polymer including a specific vinylketone phenol and a derivative thereof as radical polymerizable monomers and a positive working photosensitive resin composition containing the alkali soluble polymer and a photosensitizing agent. According to the invention, there can be provided an alkali soluble resin having high solvent resistance, high water resistance, high acid resistance, high alkali resistance, high thermal resistance, high transparency, excellent adhesiveness with a substrate, and the like and useful for the formation of a patterned resin film obtained by developing in an aqueous alkali solution and a positive working photosensitive resin composition including such an alkali soluble resin.
    Type: Grant
    Filed: November 2, 2007
    Date of Patent: March 2, 2010
    Assignee: Chisso Corporation
    Inventors: Tomohiro Etou, Eiji Watanabe, Ryouta Mineo
  • Patent number: 7465527
    Abstract: The resist material contains a photo-acid generator having an absorption peak to exposure light having a wavelength of less than 300 nm, and a second photo-acid generator having an absorption peak to exposure light having a wavelength of 300 nm or more. The method for forming a resist pattern comprises a step for selectively exposing which exposes a coating film of the resist material to an exposure light having a wavelength of less than 300 nm, and a step for selectively exposing by using an exposure light having a wavelength of 300 nm or more. The semiconductor device comprises a pattern formed by the resist pattern. The method for forming a semiconductor device comprises a step for forming a resist pattern on an underlying layer by the aforementioned manufacturing method, and a step for patterning the underlying layer by etching using the resist pattern as a mask.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: December 16, 2008
    Assignee: Fujitsu Limited
    Inventors: Junichi Kon, Ei Yano
  • Patent number: 7368205
    Abstract: The invention provides a polyamide resin having a structure represented by the formula (1), wherein about 0.1 mol % to about 30 mol % of the total amount of Y in the formula (1) has a structure represented by the formula (2), further a positive-working photosensitive resin composition comprising a diazoquinone compound, a method for producing a pattern-formed resin film using the composition, a semiconductor device and a display device using the composition, and a method for producing the semiconductor device and the display device: wherein, X is an organic group of 2 to 4 valences; Y is an organic group of 2 to 6 valences; R1 is a hydroxyl group or —O—R3 wherein m is an integer of 0 to 2; R2 is a hydroxyl group, a carboxyl group, —O—R3 or —COO—R3 wherein n is an integer of 0 to 4; R3 is an organic group having 1 to 15 carbon atoms; wherein, each of R4 and R5 is a divalent organic group; each of R6 and R7 is a monovalent organic group; n is an integer of 0 to 20.
    Type: Grant
    Filed: August 6, 2004
    Date of Patent: May 6, 2008
    Assignee: Sumitomo Bakelite Co., Ltd.
    Inventors: Toshio Banba, Takashi Hirano
  • Patent number: 7189488
    Abstract: A polyimide precursor in accordance with the present invention contains amide acid ester units, either imide units or amide acid units, and fluorine atoms bonded to some of these structural units. A polyimide precursor resin composition in accordance with the present invention contains either such a polyimide precursor or resins separately containing the structural units. Polyimide precursors in accordance with the present invention and resin compositions based on the same therefore have excellent properties and are suitably used in particular to form a particular pattern and for other purposes by impart photosensitivity to them.
    Type: Grant
    Filed: December 10, 2002
    Date of Patent: March 13, 2007
    Assignee: Kaneka Corporation
    Inventors: Toshio Yamanaka, Koji Okada, Kaoru Takagahara
  • Patent number: 7144662
    Abstract: The present invention relates to a photoresist composition having high heat resistance used in the production process of an LCD, and more particularly, to a photoresist composition having high heat resistance, capable of decreasing process tact (a way), of process simplification, and of the retrenchment of expenditures. The inventive composition facilitates this through making it possible to skip 5 processes, such as Cr metal deposition forming a metal film, and the photo/etch/PR strip/etch steps of the whole surface of the metal, by substituting the inventive composition for the usual metal film, such that N+ ion doping in production of TFT-LCD can take place due its high heat resistance.
    Type: Grant
    Filed: February 20, 2002
    Date of Patent: December 5, 2006
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Dong-Ki Lee, Sung-Chul Kang, You-Kyoung Lee, Jin-Ho Ju
  • Patent number: 7060410
    Abstract: There is provided a method of producing a resist composition which yields a resist composition with good storage stability, and no fluctuation in characteristics between production lots. There are provided: a novolak resin solution formed by adding benzoquinone to a novolak resin solution produced by dissolving a novolak resin in an organic solvent; a positive photoresist composition comprising the novolak resin solution and a photosensitive component; a positive photoresist composition comprising the novolak resin solution, a photosensitive component, and hydroquinone; and a method of producing a positive photoresist composition involving mixing the novolak resin solution described above and a photosensitive component.
    Type: Grant
    Filed: April 15, 2003
    Date of Patent: June 13, 2006
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroyuki Ohnishi, Yusuke Nakagawa, Kousuke Doi
  • 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: 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: 6864032
    Abstract: The present invention provides a method for forming an azo colorant by reaction of a diazo compound and a coupler. The coupler has a leaving group at the coupling position thereof, such that a coupling reaction rate is faster than it would be if the coupler did not have the leaving group. The coupling reaction rate constant k is preferably 0.1 (s?1) or more.
    Type: Grant
    Filed: April 18, 2001
    Date of Patent: March 8, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hisao Yamada, Mitsuyuki Tsurumi, Kazunori Nigorikawa
  • Patent number: 6849372
    Abstract: The present invention provides methods of forming and using thermally imageable composite elements which may be developed into lithographic printing plates. More specifically, the present invention provides a method of forming thermally imageable composite elements which provide substantial developer resistance in desired regions, while maintaining white light desensitivity and durability.
    Type: Grant
    Filed: July 30, 2002
    Date of Patent: February 1, 2005
    Assignee: Kodak Polychrome Graphics
    Inventors: Kevin Ray, Anthony Paul Kitson, Jian Bing Huang
  • Patent number: 6824947
    Abstract: Photosensitive compositions comprising a phenol resin having a urea bond in the main chain, planographic printing plate precursors containing the photosensitive compositions, and methods for preparing planographic printing plates using the planographic printing plate precursors are disclosed. Planographic printing plates that exhibit good durability, good exposure visual image property, and good solvent resistance; particularly superior resistance to washing oil used in UV ink printing; and superior baking property are produced.
    Type: Grant
    Filed: February 19, 2003
    Date of Patent: November 30, 2004
    Assignee: Kodak Polychrome Graphics, LLC
    Inventors: Yasuhiro Ishizuka, Yasuhiko Kojima
  • Patent number: 6790580
    Abstract: A resist material is made of a polymer or copolymer having a cyclic hydrocarbon as a skeletal structure and an alkali-soluble group to which a protective group is attached as a side chain. Because of the protective group, the resist material is insoluble in alkali solution. In addition, an acid generating agent is added to the resist material. When the acid generating agent is irradiated with a radiation ray, an acid is generated from the acid generating agent, and the protective group is detached from the alkali-soluble group by the function of the acid. Therefore, a resist film made of the resist material can be formed in a desired pattern by irradiating the resist film with the radiation ray.
    Type: Grant
    Filed: December 23, 2002
    Date of Patent: September 14, 2004
    Assignee: Fujitsu Limited
    Inventor: Satoshi Takechi
  • Publication number: 20040170914
    Abstract: The present invention relates to a positive-working photosensitive resin precursor composition which is characterized in that it contains (a) polymer in which the chief component comprises structural units of the kind where the bonding between structural units is represented by general formula (1) and (b) photoacid generator, and it can form a pattern by light irradiation and subsequent developing, and the total carboxyl groups contained in said polymer is from 0.02 to 2.0 mmol/g, and it provides a photosensitive resin composition of high sensitivity which can be developed by alkali.
    Type: Application
    Filed: March 3, 2004
    Publication date: September 2, 2004
    Inventors: Masao Tomikawa, Naoyo Okamoto, Satoshi Yoshida, Ryoji Okuda
  • Patent number: 6780561
    Abstract: Provided is a polybenzoxazole precursor having a high purity which does not contain ionic by-products. The above polybenzoxazole precursor comprises a repetitive unit represented by Formula (1): wherein A1 represents a tetravalent aromatic group; N and OH which are bonded to A1 are paired, and the respective pairs of N and OH are bonded to carbons which are adjacent to each other on the same aromatic ring; A2 represents a divalent organic group; and n represents a number of 2 to 300.
    Type: Grant
    Filed: November 26, 2002
    Date of Patent: August 24, 2004
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Mitsuru Ueda, Kazuya Ebara, Kenji Miyagawa, Kazuo Yamanaka, Yoichi Yonehara
  • Publication number: 20040142272
    Abstract: This invention relates to a negative photoresist composition with multi-reaction models. When the photoresist composition according to the present invention is used in photolithography processes employing UV light to produce cross-link reactions and multi-reactions including radical polymerization and cationic polymerization also occur. The photoresist composition can be used to control light reaction efficiency and increase reaction thoroughness, thus obtaining a high resolution pattern.
    Type: Application
    Filed: November 24, 2003
    Publication date: July 22, 2004
    Inventors: Tsing-Tang Song, Chih-Shin Chuang, Wei-Chan Tseng, Kuen-Yuan Hwang, Tsung-Yu Chen
  • Publication number: 20040142285
    Abstract: A method for forming a pattern of carbon nanotubes includes forming a pattern on a surface-treated substrate using a photolithographic process, and laminating carbon nanotubes thereon using a chemical self-assembly process so as to form the carbon nanotubes in a monolayer or multilayer structure. A monolayer or multilayer carbon nanotube pattern may be easily formed on the substrate, e.g., glass, a silicon wafer and a plastic. Accordingly, the method can be applied to form patterned carbon nanotube layers having a high conductivity, and thus will be usefully utilized in the manufacturing processes of energy storages, for example, solar cells and batteries, flat panel displays, transistors, chemical and biological sensors, semiconductor devices and the like.
    Type: Application
    Filed: October 27, 2003
    Publication date: July 22, 2004
    Applicant: Samsung Electronics Co., Ltd.
    Inventors: Myung Sup Jung, Jong Jin Park, Sung Ouk Jung, Seung Joo Seo, Bon Won Koo
  • Publication number: 20040126696
    Abstract: Positive photosensitive insulating resin compositions of the invention contain at least (A) an alkali soluble resin having a phenolic hydroxyl group, (B) a compound having a quinonediazido group, (C) crosslinked fine particles, (D) a compound containing at least two alkyletherified amino groups in the molecule, and (F) a solvent. The resin compositions have excellent resolution, electrical insulating properties and thermal shock properties. Cured products of the invention are obtained by curing these resin compositions, and they show good adhesive properties.
    Type: Application
    Filed: October 23, 2003
    Publication date: July 1, 2004
    Inventors: Katsumi Inomata, Takashi Nishioka, Atsushi Itou, Masayoshi Suzuki, Shin-ichirou Iwanaga
  • Publication number: 20040081909
    Abstract: There is provided a method of producing a resist composition which yields a resist composition with good storage stability, and no fluctuation in characteristics between production lots. There are provided: a novolak resin solution formed by adding benzoquinone to a novolak resin solution produced by dissolving a novolak resin in an organic solvent; a positive photoresist composition comprising the novolak resin solution and a photosensitive component; a positive photoresist composition comprising the novolak resin solution, a photosensitive component, and hydroquinone; and a method of producing a positive photoresist composition involving mixing the novolak resin solution described above and a photosensitive component.
    Type: Application
    Filed: April 15, 2003
    Publication date: April 29, 2004
    Inventors: Hiroyuki Ohnishi, Yusuke Nakagawa, Kousuke Doi
  • Publication number: 20040013965
    Abstract: A positive photosensitive composition for use with a radiation source comprises one or more polymers capable of being dissolved in an alkaline aqueous solution and a compound which, upon being heated, releases gas. The composition is stable in its state before exposure and has an excellent handling property. The sensitivity of a recording layer based on the composition of this invention is increased without compromising the handling characteristics. In addition radiation sensitive-elements based on the composition of the invention have good development latitude.
    Type: Application
    Filed: March 17, 2003
    Publication date: January 22, 2004
    Inventors: Livia T. Memetea, Jonathan W. Goodin, Nicholas Bradford, Juana G. Jaramillo, Cheng Yang
  • 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: 6641971
    Abstract: A chemically amplified resist composition comprises an aqueous base soluble polymer or copolymer having one or more polar functional groups, wherein at least one of the functional groups is protected with a cycloaliphatic silyl ketal group but may also include other protecting groups as well as unprotected acidic functionalities. A ratio of protected to unprotected acidic functionalities is preferably selected to most effectively modulate a solubility of the resist composition in an aqueous base or other developer. The resist composition further comprises an acid generator, preferably a photoacid generator (PAG), and a casting solvent, and may also include other components, such as, a base additive and/or surfactant.
    Type: Grant
    Filed: June 15, 2001
    Date of Patent: November 4, 2003
    Assignee: International Business Machines Corporation
    Inventors: Wu-Song Huang, David R. Medeiros
  • Patent number: 6566040
    Abstract: First, a hole pattern or a separation pattern of a first resist that is capable of supplying acid is formed on a semiconductor substrate. Then, a crosslinked film (organic frame) is formed on the side wall of the first resist pattern to obtain a resist pattern having a reduced hole diameter or separation width. Then, the hole diameter or the separation width is further reduced by causing thermal reflow of the crosslinked film. Finally, the semiconductor substrate is etched by using a resulting resist pattern as a mask.
    Type: Grant
    Filed: January 20, 1999
    Date of Patent: May 20, 2003
    Assignees: Mitsubishi Denki Kabushiki Kaisha, Ryoden Semiconductor System Engineering Corporation
    Inventors: Kanji Sugino, Takeo Ishibashi, Takayuki Shoya
  • Publication number: 20030059706
    Abstract: A positive photoresist composition includes an alkali-soluble novolak resin(A), an alkali-soluble acrylic resin (B) and a quinonediazido-group-containing compound (C) and is used for the formation of a thick film 5 to 100 &mgr;m thick. The ingredient (B) includes 30% to 90% by weight of a unit (b1) derived from a polymerizable compound having an ether bond and 2% to 50% by weight of a unit (b2) derived from a polymerizable compound having a carboxyl group. The composition is applied on a substrate and thereby yields a photoresist film. Likewise, the composition is applied onto a substrate on an electronic part, is patterned, is plated and thereby yields bumps.
    Type: Application
    Filed: March 5, 2002
    Publication date: March 27, 2003
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Kouichi Misumi, Koji Saito, Toshiki Okui, Hiroshi Komano
  • Publication number: 20030003393
    Abstract: There is provided a positive photoresist for near-field exposure excellent in light utilization efficiency even with small layer thickness of the photoresist layer for image formation, and allowing for reduced pattern edge roughness, and a photolithography method including a step of exposing by the near-field exposure the photoresist layer for image formation made thereof. In a positive photoresist containing an alkali-soluble novolak resin and a quinone diazide compound, the film thickness of the photoresist at the time of exposure is not larger than 100 nm, and the absorption coefficient of the photoresist &agr; (&mgr;m−1) for the exposure light is such that 0.5≦&agr;≦7.
    Type: Application
    Filed: June 10, 2002
    Publication date: January 2, 2003
    Inventors: Takako Yamaguchi, Yasuhisa Inao
  • Patent number: 6436593
    Abstract: Disclosed are a positive type photosensitive resin composition which comprises (A) a polyimide precursor or a polyoxazole precursor having a group represented by —OR, wherein R represents a monovalent group constituting a acetal or ketal, an alkoxyalkyl group or an alkylsilyl group, which can be converted into a hydrogen atom by decomposition with an action of an acid, in the molecule which is bonded to an aromatic ring, and (B) a compound which generates an acid by irradiating radiation, a process for producing the same and electronic parts using the same.
    Type: Grant
    Filed: September 21, 2000
    Date of Patent: August 20, 2002
    Assignees: Hitachi Chemical DuPont Microsystems Ltd., Hitachi Chemical DuPont Microsystems LLC
    Inventors: Tomonori Minegishi, Makoto Kaji
  • Publication number: 20020106577
    Abstract: Provided is a photosensitive copper paste permitting the formation of a fine and thick copper pattern having high adhesion to a substrate, and having excellent preservation stability without causing gelation, and a method of forming a copper pattern, a circuit board and a ceramic multilayer substrate using the photosensitive copper paste. The photosensitive copper paste includes a mixture of an organic binder having an acid functional group, a copper powder and a photosensitive organic component. The copper powder has a surface layer having a thickness of at least 0.1 &mgr;m from the surface composed CuO as a main component. The copper powder also has an oxygen content of about 0.8% to 5% by weight.
    Type: Application
    Filed: November 30, 2001
    Publication date: August 8, 2002
    Applicant: Murata Manufacturing Co., Ltd.
    Inventor: Masahiro Kubota
  • Patent number: 6384103
    Abstract: Radiation-sensitive resin composition having excellent and well-balanced various properties required for photoresist, such as sensitivity, pattern profile and heat resistance. The radiation-sensitive resin composition comprises an alkali-soluble resin and a photosensitizer having a quinonediazide group. The alkali-soluble resin is a phenol novolak resin which is treated by a thin film distillation method to selectively remove monomer and dimer. The novolak resin treated by thin film distillation method preferably shows the following ratio in area in its profile in gel permeation chromatography with a detector at 280 nm: B2/B1≧0.95; C2/(A2+B2+C2)≦0.060 wherein A1 is a high-molecular region, B1 is a middle-molecular region, and C1 is a monomer/dimer region before the treatment of the starting novolak resin, and A2, B2 and C2 are the corresponding counterparts after the treatment of the novolak resin.
    Type: Grant
    Filed: December 1, 2000
    Date of Patent: May 7, 2002
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Akio Arano, Kenji Yamamoto
  • Patent number: 6274286
    Abstract: A chemically amplified positive resist composition comprising at least one basic compound of the following general formula (1) or (2): wherein R1, R2, R3, R7, and R8 are independently normal, branched or cyclic alkylene groups having 1 to 20 carbon atoms, R4, R5, R6, R9, and R10 are independently hydrogen, alkyl groups having 1 to 20 carbon atoms or amino groups, R4 and R5, R5 and R6, R4 and R6, or R8, R5 and R5, and R9 and R10, taken together, may form a ring, letters k, m and n are integers of 0 to 20, with the proviso that hydrogen is excluded from R4, R5, R6, R9 and R10 when k, m or n is equal to 0. The resist compositions of the present invention are effective for preventing resist films from thinning and for increasing the focus margin of an isolated pattern.
    Type: Grant
    Filed: June 26, 1998
    Date of Patent: August 14, 2001
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Tsunehiro Nishi, Takeshi Nagata, Shigehiro Nagura
  • Patent number: 5928841
    Abstract: Disclosed is a method of forming a pattern on a substrate, comprising a step of forming a light-sensitive layer containing an aromatic compound on a substrate, a step of patternwise exposing the light-sensitive layer with a light having a wavelength range shorter than the maximum wavelength; in the third absorption band from the long-wave side in the absorption spectrum of the aromatic compound and longer than the maximum wavelength in the fourth absorption band from the same, thereby to cause a photochemical reaction in the light-sensitive layer, and a step of developing the exposed light-sensitive layer, optionally after heat-treating the layer, so as to selectively remove the exposed area of the layer or leave the area as it is. The method gives a pattern having a high resolving power and an excellent dry-etching resistance.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: July 27, 1999
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Toru Ushirogouchi, Makoto Nakase, Takuya Naito, Koji Asakawa
  • Patent number: 5928833
    Abstract: A radiation sensitive material comprises particles including a water-insoluble heat-softenable core surrounded by a shell which is soluble or swellable in aqueous medium. The material also includes a radiation sensitive component which, on exposure to radiation, causes the solubility characteristics of the material to change. The material may be positive- or negative-working and may be coated onto a substrate from aqueous media to form a radiation sensitive plate which, after image-wise exposure, can be developed in aqueous media and then heated to cause the particles to coalesce and form a durable printing image.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: July 27, 1999
    Assignee: DuPont (U.K.) Ltd.
    Inventors: Andrew E. Matthews, David E. Murray, Allen P. Gates, John R. Wade, Michael J. Pratt, William A. King
  • Patent number: 5908730
    Abstract: Proposed is a positive- or negative-working chemical-sensitization photoresist composition having advantages in respect of the contrast and resolution of patterning, photosensitivity and cross sectional profile of the patterned resist layer as well as in respect of stability of the latent image formed by pattern-wise exposure to light before post-exposure baking treatment. The composition comprises: (A) 100 parts by weight of a film-forming resinous ingredient which causes a change, i.e. increase or decrease, of solubility in an aqueous alkaline solution by the interaction with an acid; and (B) from 0.5 to 20 parts by weight of a radiation-sensitive acid-generating agent which is a diazomethane compound represented by the general formulaR.sup.1 --SO.sub.2 --C(.dbd.N.sub.2)--SO.sub.2 --R.sup.2,in which R.sup.1 and R.sup.2 are each, independently from the other, a monovalent cyclic group substituted on the cyclic nucleus by an acid-dissociable group such as a tert-butoxycarbonyl and acetal groups.
    Type: Grant
    Filed: July 22, 1997
    Date of Patent: June 1, 1999
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazuyuki Nitta, Kazufumi Sato, Akiyoshi Yamazaki, Yoshika Sakai, Toshimasa Nakayama
  • Patent number: 5866295
    Abstract: The present invention relates to novel photosensitive quinolone compounds, specifically novel 3-diazo 2,4-quinolinedione compounds, that may be used in a variety of applications, such as, photosensitive coating compositions, pharmaceuticals, agricultural, amongst others. The invention further relates to a process for making the novel photosensitive 3-diazo 2,4-quinolinedione compounds. These compounds are particularity useful as a photoactive component in a positive working photoresist composition, particularity for use as a deep ultraviolet (UV) photoresist.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: February 2, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Joseph E. Oberlander, Dana L. Durham, Dinesh N. Khanna
  • Patent number: 5648195
    Abstract: A radiation-sensitive resist composition for manufacturing highly resolved relief structures is characterized by the following components:a film-forming base polymer;a radiation-active component that releases an acid when irradiated;a radiation-sensitive ester-former; anda solvent.
    Type: Grant
    Filed: January 5, 1995
    Date of Patent: July 15, 1997
    Assignee: Siemens Aktiengesellschaft
    Inventors: Michael Sebald, Siegfried Birkle, Karin Preissner, Hans-Jurgen Bestmann
  • Patent number: 5637436
    Abstract: Ternary mixtures of C.sub.4 to C.sub.8 alkyl acetate, C.sub.4 to C.sub.8 alkyl alcohol, and water, formulated to have a flash point of above 100.degree. F., are disclosed, particularly for use in edge residue removal processes in the fabrication of integrated circuits and like products.
    Type: Grant
    Filed: April 4, 1995
    Date of Patent: June 10, 1997
    Assignee: Hoechst Celanese Corporation
    Inventor: Donald W. Johnson
  • Patent number: 5582952
    Abstract: A photosensitive lithographic printing plate which provides a wide range of proper conditions for development, high impression capacity, a flexible film sufficient in adhesion to a support and excellent processing suitability with a weakly alkaline developer (pH 12.5 or less) is disclosed. The photosensitive lithographic printing plate comprises a support and a photosensitive layer provided thereon, wherein the photosensitive layer is formed from a photosensitive composition containing at least a two-equivalent coupler residue-containing compound and a photosensitive compound or a photosensitive mixture acting as a positive type.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: December 10, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koichi Kawamura, Keiji Akiyama, Toshifumi Inno, Katsuji Kitatani
  • 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: 5543265
    Abstract: Changing (varying, irregular) resist thickness on semiconductor wafers having irregular top surface topography or having different island sizes, affects the percent reflectance (and absorption efficiency) of incident photolithographic light, and consequently the critical dimensions of underlying features being formed (e.g., polysilicon gates). A low solvent content resist solution that can be applied as an aerosol provides a more uniform thickness resist film, eliminating or diminishing photoresist thickness variations. A top antireflective coating (TAR) also aids in uniformizing reflectance, despite resist thickness variations. The two techniques can be used alone, or together. Hence, better control over underlying gate size can be effected, without differential biasing.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 6, 1996
    Assignee: LSI Logic Corporation
    Inventor: Mario Garza
  • Patent number: 5518864
    Abstract: Disclosed is a photosensitive resin composition, containing a polyamic acid derivative having a repeating unit represented by general formula (1) given below and a photosensitive agent: ##STR1## where, R.sup.1 represents a tetravalent organic group, R.sup.2 represents a divalent organic group, and R.sup.3 and R.sup.4 represent a monovalent organic group, at least one of R.sup.3 and R.sup.4 being an organic group having at least on hydroxyl group bonded to an aromatic ring. A semiconductor substrate is coated with the photosensitive resin composition, followed by exposing the coated film to light through a patterning mask and subsequently applying a development and a heat treatment so as to form a polyimide film pattern. A baking treatment also be applied immediately after the exposure step. The photosensitive resin composition of the present invention performs the function of a positive or negative photoresist film and the function of a polyimide protective film on a semiconductor substrate.
    Type: Grant
    Filed: March 30, 1994
    Date of Patent: May 21, 1996
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Masayuki Oba, Rumiko Hayase, Naoko Kihara, Shuzi Hayase, Yukihiro Mikogami, Yoshihiko Nakano, Naohiko Oyasato, Shigeru Matake, Kei Takano
  • Patent number: 5482816
    Abstract: A radiation-sensitive composition comprising (A) a polymer having a recurring unit represented by formula (1): ##STR1## wherein R.sup.1 represents a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.2 represents --OR.sup.3 or --NR.sup.4 R.sup.5 in which R.sup.3 is a hydrogen atom, a straight-chain alkyl group, a cyclic alkyl group, an aryl group, an aralkyl group, a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.4 and R.sup.5, which may be the same or different, are hydrogen atoms, straight-chain alkyl groups, cyclic alkyl groups, aralkyl groups or aryl groups, and (B) a radiation-sensitive acid forming agent.
    Type: Grant
    Filed: June 21, 1994
    Date of Patent: January 9, 1996
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Makoto Murata, Mikio Yamachika, Yoshiji Yumoto, Takao Miura
  • Patent number: 5426017
    Abstract: Ternary mixtures of C.sub.4 to C.sub.8 alkyl acetate, C.sub.4 to C.sub.8 alkyl alcohol, and water, formulated to have a flash point of above 100.degree. F., are disclosed, particularly for use in edge residue removal processes in the fabrication of integrated circuits and like products.
    Type: Grant
    Filed: March 10, 1993
    Date of Patent: June 20, 1995
    Assignee: Hoechst Celanese Corporation
    Inventor: Donald W. Johnson
  • Patent number: 5348835
    Abstract: Disclosed is a photosensitive resin composition, containing a polyamic acid derivative having a repeating unit represented by general formula (1) given below and a photosensitive agent: ##STR1## where, R.sup.1 represents a tetravalent organic group, R.sup.2 represents a divalent organic group, and R.sup.3 and R.sup.4 represent a monovalent organic group, at least one of R.sup.3 and R.sup.4 being an organic group having at least on hydroxyl group bonded to an aromatic ring. A semiconductor substrate is coated with the photosensitive resin composition, followed by exposing the coated film to light through a patterning mask and subsequently applying a development and a heat treatment so as to form a polyimide film pattern. A baking treatment also be applied immediately after the exposure step. The photosensitive resin composition of the present invention performs the function of a positive or negative photoresist film and the function of a polyimide protective film on a semiconductor substrate.
    Type: Grant
    Filed: September 27, 1991
    Date of Patent: September 20, 1994
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Masayuki Oba, Rumiko Hayase, Naoko Kihara, Shuzi Hayase, Yukihiro Mikogami, Yoshihiko Nakano, Naohiko Oyasato, Shigeru Matake, Kei Takano
  • Patent number: 5346803
    Abstract: A photoresist composition comprises a polymer of the following formula (1): ##STR1## wherein R.sup.1 is a substituted or unsubstituted aromatic group or --(CH.sub.2).sub.p --SiR.sup.3 wherein R.sup.3 is a methyl or ethyl group and p is equal to 0 or 1, R.sup.2 is a hydrogen atom or methyl group, t-Bu is a tertiary-butyl group, and n/(m+n) is in the range of from 0.1 to 0.9.The polymer of formula (1) can form a positive working two-component photoresist composition with a photoacid generator. The polymer of formula (1) can also be used as an alkali soluble resin and in this regard, form a positive working three-component photoresist composition with a photoacid generator and a dissolution inhibitor having at least one group which is unstable to acid. Alternatively, the polymer of formula (1) can be used as a dissolution inhibitor and in this regard, form a positive working three-component photoresist composition with another alkali soluble resin and a photoacid generator.
    Type: Grant
    Filed: September 15, 1993
    Date of Patent: September 13, 1994
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: James V. Crivello, Sang-Yeon Shim
  • Patent number: 5340682
    Abstract: A positive-working radiation-sensitive mixture is disclosed which contains as essential constituents:a) an .alpha.-carbonyl-.alpha.-sulfonyl-diazomethane, which forms a strong acid on irradiation, of the general formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, denote an alkyl-, cycloalkyl-, aryl- or heteroaryl radicalb) a compound having at least one C--O--C or C--O--Si bond which can be cleaved by acid, andc) a water-insoluble binder which is soluble or at least swellable in aqueous-alkaline solutions.The radiation-sensitive mixture according to the invention is notable for a high sensitivity over a wide spectral range. It also exhibits a high thermal stability and does not form any corrosive photoylsis products on exposure to light.
    Type: Grant
    Filed: April 9, 1993
    Date of Patent: August 23, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Hans-Joachim Merrem, Juergen Lingnau, Ralph Dammel, Horst Roeschert