Nitrogen Compound Containing Patents (Class 430/919)
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Patent number: 6696217Abstract: A photosensitive monomer including a methylene butyrolactone derivative represented by the following formula: wherein R1 is a hydrogen atom or alkyl group, R2 is an acid-labile group, X is a hydrogen atom, or substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and Y is a substituted or unsubstitued alkyl group or alicyclic hydrocarbon group having 1 to 20 carbon atoms.Type: GrantFiled: February 20, 2002Date of Patent: February 24, 2004Assignee: Samsung Electronics Co., Ltd.Inventors: Kwang-sub Yoon, Sang-gyun Woo
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Patent number: 6692897Abstract: A positive resist composition comprises: (A) a resin having an aliphatic cyclic hydrocarbon group and increasing the solubility to an alkali developer by the action of an acid; (B) a compound generating an acid upon irradiation with an actinic ray or radiation; and (C) a nitrogen-containing compound having in the molecule at least one partial structure represented by following formula (I).Type: GrantFiled: July 12, 2001Date of Patent: February 17, 2004Assignee: Fuji Photo Film Co., Ltd.Inventors: Toru Fujimori, Yasumasa Kawabe, Hajime Nakao
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Patent number: 6692893Abstract: Onium salts of arylsulfonyloxynaphthalenesulfonate anions with iodonium or sulfonium cations are novel. A chemically amplified resist composition comprising the onium salt as a photoacid generator is suited for microfabrication, especially by deep UV lithography because of many advantages including improved resolution, improved focal latitude, minimized line width variation or shape degradation even on long-term PED, minimized debris after coating, development and peeling, and improved pattern profile after development.Type: GrantFiled: October 23, 2001Date of Patent: February 17, 2004Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Jun Watanabe, Takeshi Nagata, Jun Hatakeyama
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Publication number: 20040029037Abstract: The present invention provides a sulfonate of the formula (I′): 1Type: ApplicationFiled: May 19, 2003Publication date: February 12, 2004Inventors: Akira Kamabuchi, Yasunori Uetani, Hiroshi Moriuma
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Publication number: 20040018445Abstract: A chemical amplification type positive resist composition comprising:Type: ApplicationFiled: July 21, 2003Publication date: January 29, 2004Inventors: Makoto Akita, Satoshi Yamaguchi
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Patent number: 6673516Abstract: A coating composition for a chemically amplified positive resist includes (A) an acid generator which generates an acid upon irradiation with active light or radiant ray, (B) a resin ingredient which exhibits increased solubility in an alkaline aqueous solution by action of an acid, (C) an organic solvent, and (D) an octanone in a proportion of from 0.1 to 5 parts by weight relative to 100 parts by weight of the ingredient (B). Using this coating composition, a method of patterning a resist. The coating composition and the method can yield a positive resist having improved definition and depth of focus.Type: GrantFiled: November 6, 2001Date of Patent: January 6, 2004Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Satoshi Kumon, Kazufumi Sato
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Publication number: 20030215738Abstract: Photoacid generators are provided by O-arylsulfonyl-oxime compounds having formula (1) wherein R is H, F, Cl, NO2, alkyl or alkoxy, n is 0 or 1, m is 1 or 2, r is 0 to 4, r′ is 0 to 5, k is 0 to 4, and G′ and G″ are S or —CH═CH—. Chemically amplified resist compositions comprising the photoacid generators have many advantages including improved resolution, improved focus latitude, minimized line width variation or shape degradation even on long-term PED, and improved pattern profile after development. Because of high resolution, the compositions are suited for microfabrication, especially by deep UV lithography.Type: ApplicationFiled: March 21, 2003Publication date: November 20, 2003Inventors: Youichi Ohsawa, Katsuhiro Kobayashi, Katsuya Takemura, Junji Tsuchiya, Kazunori Maeda
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Publication number: 20030215748Abstract: Photoresist compositions having a resin binder with an acid labile blocking group with 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.Type: ApplicationFiled: June 9, 2003Publication date: November 20, 2003Applicant: Shipley Company, L.L.C.Inventors: James W. Thackeray, James F. Cameron, Roger F. Sinta
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Publication number: 20030203305Abstract: 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: ApplicationFiled: March 26, 2003Publication date: October 30, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Shoichiro Yasunami, Yutaka Adegawa, Koji Shirakawa
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Publication number: 20030198894Abstract: A resist composition for an electron beam, EUV or X-ray comprising (A1) a compound that has a reduction potential higher than that of diphenyl iodonium salt and generates an acid upon irradiation of an actinic ray or radiation.Type: ApplicationFiled: February 11, 2003Publication date: October 23, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Kazuyoshi Mizutani, Hyou Takahashi
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Publication number: 20030190554Abstract: A plate-making method of a printing plate comprising exposing a printing plate precursor having a photosensitive layer comprising a photopolymerizable composition containing (i) a crosslinking agent having two ethylenic polymerizable groups and (ii) a crosslinking agent having three or more ethylenic polymerizable groups, and development processing the exposed printing plate precursor with an alkali developer having a pH of not more than 12.5.Type: ApplicationFiled: August 29, 2002Publication date: October 9, 2003Inventor: Kazuto Kunita
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Publication number: 20030113660Abstract: A sulfonyloxime compound is provided which is represented by a general formula (1): 1Type: ApplicationFiled: August 23, 2002Publication date: June 19, 2003Inventors: Eiji Yoneda, Tatsuya Toneri, Yong Wang, Tsutomu Shimokawa
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Patent number: 6576393Abstract: Disclosed are a composition for a resist underlayer film excellent in reproducibility of a resist pattern, excellent in adhesion to a resist, excellent in resistance to a developing solution used after exposure of the resist and decreased in film loss in oxygen ashing of the resist; and a method for producing the same, the composition comprising: both or either of a hydrolysate and a condensate of (A) at least one compound selected from the group consisting of (A-1) a compound represented by the following general formula (1): R1aSi(OR2)4−a (1) wherein R1 represents a hydrogen atom, a fluorine atom or a univalent organic group, R2 represents a univalent organic group, and a represents an integer of 0 to 2, and (A-2) a compound represented by the following general formula (2): R3b(R4O)3−bSi—(R7)d—Si(OR5)3−cR6c (2) wherein R3, R4, R5 and R6, which may be the same or different, each represent univalent organic groups, b and c, which may be the same or diffeType: GrantFiled: April 7, 2000Date of Patent: June 10, 2003Assignee: JSR CorporationInventors: Hikaru Sugita, Akio Saito, Kinji Yamada, Michinori Nishikawa, Yoshihisa Ohta, Yoshiji Yuumoto
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Patent number: 6569596Abstract: A negative working chemical amplification type resist composition, which is capable of giving more improved resolution; and comprises an alkali-soluble resin, a cross-linking agent, a N-substituted succinimide compound represented by the following formula (I): wherein R represents an unsubstituted or substituted alkyl, an alicyclic hydrocarbon residue, an aryl or a camphor group, and an acid generator other than the above N-substituted succinimide compound is provided.Type: GrantFiled: May 31, 2000Date of Patent: May 27, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Yasunori Uetani, Airi Yamada, Hiroki Inoue
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Patent number: 6569603Abstract: There are disclosed a light-sensitive composition which comprises (A) a polymer having a phenyl group substituted by a vinyl group at a side chain, (B) a photopolymerization initiator and (C) a sensitizer which sensitizes the photo-polymerization initiator, or a light-sensitive composition which comprises (A′) a polymer, the above-mentioned (B) and (C), and (D) a monomer having at least two phenyl groups each of which is substituted by a vinyl group in the molecule of the monomer; and a method of forming a relief image which comprises coating the light-sensitive composition as mentioned above on a support, exposing the composition by exposure or scanning exposure and developing the same to form a relief image on the support.Type: GrantFiled: January 30, 2001Date of Patent: May 27, 2003Assignee: Mitsubishi Paper Mills LimitedInventor: Akira Furukawa
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Patent number: 6562542Abstract: An image-forming material is described, comprising on an support an acid-generating agent selected from a sulfonic acid ester of a specific structure generating an acid by the action of heat and the polymer thereof, and a compound causing a light absorption change in the absorption region of from 350 to 700 nm by an intramolecular or intermolecular reaction by the action of an acid. The image-forming material has a high sensitivity and excellent storage stability and gives low haze and good images in the case of performing image formation using a high-output laser light.Type: GrantFiled: March 28, 2001Date of Patent: May 13, 2003Assignee: Fuji Photo Film Co., Ltd.Inventors: Atsuhiro Ohkawa, Seiya Sakurai
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Patent number: 6551761Abstract: This invention relates to &agr;-ammonium ketones, iminium ketones or amidinium ketones in the form of their tetraaryl- or triarylalkylborate salts which can be photochemically converted into amines, imines or amidines as well as to a process for their preparation. This invention also relates to base-polymerisable or crosslinkable compositions comprising these &agr;-ammonium ketones, iminium ketones or amidinium ketones in the form of their tetra- or triarylalkylborate salts, to a process for carrying out photochemically induced, base-catalysed reactions as well as to their use as photoinitiators for base-catalysed reactions.Type: GrantFiled: September 7, 2000Date of Patent: April 22, 2003Assignee: Ciba Specialty Chemical CorporationInventors: VĂ©ronique Hall-Goulle, Sean Colm Turner, Allan Francis Cunningham
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Publication number: 20030059705Abstract: The present invention provides a photopolymerizable composition comprising a polymerizable compound including an addition-polymerizable unsaturated bond, a photo-radical-generating agent, and an amine compound represented by the following general formula (I) and a recording material comprising a recording layer containing the photopolymerizable composition: 1Type: ApplicationFiled: April 12, 2002Publication date: March 27, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Hirotaka Matsumoto, Shintaro Washizu
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Publication number: 20030044717Abstract: A positive photosensitive composition comprising (A1) a compound that generates an alkanesulfonic acid in which the &agr;-position is substituted with a fluorine atom upon irradiation of an actinic ray or radiation, (A2) an onium salt of an alkanesulfonic acid in which the &agr;-position is not substituted with a fluorine atom, and (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase a solubility rate in an alkali developing solution.Type: ApplicationFiled: June 20, 2002Publication date: March 6, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventor: Kunihiko Kodama
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Publication number: 20030008241Abstract: A positive-working resist composition comprising (A) a specific resin which has an aliphatic cyclic hydrocarbon group and enhances in the dissolution rate in an alkaline developing solution by an action of an acid, and (B) a specific compound generating an acid by irradiation of actinic ray or radiation. The composition is excellent in the resolving power and the exposure margin, and can be suitably used for micro-photofabrication using far ultraviolet rays, particularly ArF eximer laser beams.Type: ApplicationFiled: March 11, 2002Publication date: January 9, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Kenichiro Sato, Kunihiko Kodama
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Patent number: 6485886Abstract: New oxime derivatives of formula (I) or. (II), wherein m is 0 or 1; R1 inter alia is phenyl, naphthyl, anthracyl, phenanthryl or a heteroaryl radical; R′1 is for example C2-C12alkylene, phenylene, naphthylene; R2 is CN; R3 is C2-C6haloalkanoyl, halobenzoyl, a phosphoryl or an organosilyl group; R4, R5, R10 and R11 inter alia are hydrogen, C1-C6alkyl, C1-C6alkoxy; R6 inter alia is hydrogen phenyl, C1-C12alkyl; R7 and R8 inter alia are hydrogen, C1-C12alkyl; or R7 and R8, together with the nitrogen atom to which they are bonded, form a 5-, 6 or 7-membered ring; R9 is for example C1-C12alkyl; and A inter alia is S, O, NR7a; are useful as latent acids, especially in photoresist applications.Type: GrantFiled: April 24, 2001Date of Patent: November 26, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Hitoshi Yamato, Toshikage Asakura, Jean-Luc Birbaum, Kurt Dietliker
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Patent number: 6479210Abstract: A chemically amplified resist composition is disclosed which shows a high sensitivity, high resolution, excellent processing adaptability and excellent processing stability, which can form good pattern profile and which is suited as a finely processable material for use in manufacturing integrated circuit elements or the like. The chemically amplified resist composition comprises at least (a) an organic material containing a substituent or substituents capable of being released in the presence of an acid and (b) compounds capable of generating an acid upon exposure to radiation (acid-generators), composed of at least one onium salt and at least one of sulfone compounds and sulfonate compounds. This chemically amplified resist composition preferably further contains a basic compound.Type: GrantFiled: April 3, 2000Date of Patent: November 12, 2002Assignee: Clariant Finance (BVI) LimitedInventors: Yoshiaki Kinoshita, Satoru Funato, Yuko Yamaguchi
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Patent number: 6432609Abstract: The present invention proposes a novel photoacid generator, and a method of undergoing a photoacid-catalyzed reaction of a resin system, e.g. a curing reaction. The photoacid generator has the following structure of formula (I) wherein R′ and R are radicals which enable the photoacid generator (I) forming a compound (II) and a proton acid RH under irradiation: The present invention also discloses positive tone and negative tone photoresists containing the photoacid generator (I).Type: GrantFiled: July 21, 2000Date of Patent: August 13, 2002Assignee: National Science CouncilInventor: Jui-Hsiang Liu
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Patent number: 6423456Abstract: A composition used as a resist in the manufacture of electronic parts, for example printed circuits, and which is rendered soluble in a developer by patternwise delivery of heat, comprises a polymer of general formula (I), wherein R1 represents a hydrogen atom or alkyl group, R2 represents a hydrogen atom or alkyl group, R3 represents a hydrogen atom or alkyl group, and R4 represents hydroxyalkyl group, and wherein the ratio n/m is in the range 10/1 to 1/10.Type: GrantFiled: April 9, 2001Date of Patent: July 23, 2002Assignee: Kodak Polychrome Graphics LLCInventors: Anthony Paul Kitson, Peter Andrew Reath Bennett, Kevin Barry Ray
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Patent number: 6406831Abstract: Provided is a chemically amplified resist composition comprising a photoacid generator and an acid sensitive resin which has a huge molecular weight and from which the dissolution controlling group is cleaved owing to the decomposition of the partially crosslinked structure by the acid released from the photoacid generator. By the above-described composition, ultrafine processing can be carried out with improved focal depth, whereby an excellent rectangular pattern can be formed.Type: GrantFiled: November 20, 2001Date of Patent: June 18, 2002Assignee: NEC CorporationInventor: Mitsuharu Yamana
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Patent number: 6399273Abstract: Water-processable positive-tone photoresists comprising a water-soluble polymer, wherein the polymer contains a heat-labile functional group that renders the polymer insoluble in water or an aqueous base upon heat treatment, and an acid-labile functional group that restores said water or aqueous base solubility to the polymer upon irradiation in the presence of a water-processable photoacid generator, are described. Also described are the methods of making such polymers and photoresists.Type: GrantFiled: August 14, 2000Date of Patent: June 4, 2002Assignee: Board of Regents, University of Texas SystemInventors: Shintaro Yamada, Timo Rager, C. Grant Willson
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Patent number: 6395451Abstract: The present invention relates to a photoresist composition containing Photo Base Generator (PBG), more specifically, to a photoresist composition which comprises (a) photoresist resin, (b) photo acid generator, (c) organic solvent and further (d) photo base generator. The photo base generator is preferably selected from benzyloxycarbonyl compound of Chemical Formula 1 or O-acyloxime compound of Chemical Formula 2, which prevents a slopping pattern formation and a severe I/D Bias occurrence. wherein, R′, R1 to R6 are defined in accordance with the Specification.Type: GrantFiled: September 21, 2000Date of Patent: May 28, 2002Assignee: Hyundai Electronics Industries Co., Ltd.Inventors: Jae Chang Jung, Keun Kyu Kong, Jin Soo Kim, Ki Ho Baik
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Patent number: 6376152Abstract: A positive photoresist composition comprises (A) a compound which generates an acid upon irradiation with an actinic ray or radiation, (B) a resin which is insoluble or sparingly soluble in alkali but becomes soluble in alkali by the action of an acid, and (C) a nitrogen-containing compound containing at least one partial structure represented by formula (I) shown below in its molecule: The positive photoresist composition of the present invention is suitable for exposure to a far ultraviolet ray, particularly a KrF excimer laser beam, improved in line edge roughness and also excellent in sensitivity, resolution, depth of focus and resist profile.Type: GrantFiled: February 5, 2001Date of Patent: April 23, 2002Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasumasa Kawabe, Shinichi Kanna, Fumiyuki Nishiyama
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Patent number: 6372406Abstract: Deactivated aromatic amines are useful to improve shelf life and performance of acid-catalyzed photoresist compositions without adverse interaction with radiation-sensitive acid generator components in said resist. The compositions are especially useful in photolithography processes used in forming integrated circuits and other miniaturized components.Type: GrantFiled: November 6, 2000Date of Patent: April 16, 2002Assignee: International Business Machines CorporationInventors: William R. Brunsvold, Ahmad D. Katnani, Pushkara R. Varanasi
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Publication number: 20020042022Abstract: Compounds of the formula I 1Type: ApplicationFiled: May 18, 2001Publication date: April 11, 2002Inventors: David George Leppard, Manfred Kohler, Andreas Valet
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Patent number: 6338934Abstract: A photo resist composition contains a polymer resin, a first photo acid generator (PAG) requiring a first dose of actinic energy to generate a first photo acid, and a photo base generator (PBG) requiring a second dose of actinic energy, different from the first dose, to generate a photo base. The amounts and types of components in the photo resist are selected to produce a hybrid resist image. Either the first photo acid or photo base acts as a catalyst for a chemical transformation in the resist to induce a solubility change. The other compound is formulated in material type and loading in the resist such that it acts as a quenching agent. The catalyst is formed at low doses to induce the solubility change and the quenching agent is formed at higher doses to counterbalance the presence of the catalyst. Accordingly, the same frequency doubling effect of conventional hybrid resist compositions may be obtained, however, either a line or a space may be formed at the edge of an aerial image.Type: GrantFiled: August 26, 1999Date of Patent: January 15, 2002Assignee: International Business Machines CorporationInventors: Kuang-Jung R. Chen, Mark C. Hakey, Steven J. Holmes, Wu-Song Huang, Paul A. Rabidoux
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Publication number: 20010044072Abstract: The invention provides new photoresist compositions that contain a resin binder and a blend of non-ionic and ionic PAGS. Preferred resists of the invention preferably are imaged with 248 nm and/or 193 nm exposure wavelengths to provide highly resolved small dimension features.Type: ApplicationFiled: May 18, 2001Publication date: November 22, 2001Applicant: Shipley Company, L.L.C.Inventor: Peter Trefonas
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Publication number: 20010041303Abstract: Provided is a positive photoresist composition which comprises (A) a resin which contains a repeating unit represented by formula (I) shown below and a repeating unit represented by formula (II) shown below and whose solubility in an alkaline developing solution increases by the action of an acid and (B) a compound which generates an acid upon irradiation with an actinic ray or radiation, 1Type: ApplicationFiled: February 22, 2001Publication date: November 15, 2001Inventor: Kenichiro Sato
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Patent number: 6261736Abstract: The pattern forming material of the present invention includes a polymer having a group which generates an acid when the polymer is irradiated with an energy beam or heated and a compound which generates a base when the compound is irradiated with an energy beam. The polymer is a binary polymer or a polymer of a higher degree obtained by polymerizing another group with a compound represented by the following general formula: where R1 indicates a hydrogen atom or an alkyl group, and R2 and R3 independently indicate a hydrogen atom, an alkyl group, a phenyl group or an alkenyl group, or together indicate a cyclic alkyl group, a cyclic alkenyl group, a cyclic alkyl group having a phenyl group or a cyclic alkenyl group having a phenyl group.Type: GrantFiled: October 12, 1999Date of Patent: July 17, 2001Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Masayuki Endo, Masamitsu Shirai, Masahiro Tsunooka
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Patent number: 6261738Abstract: Compounds of formula I, II and III, wherein wherein R1 is for example hydrogen, C1-C12alkyl, C3-C30cycloalkyl, C2-C12alkenyl, C4-C8cycloalkenyl, phenyl, which is unsubstituted or substituted, naphthyl, anthracyl or phenanthryl, unsubstituted or substituted, heteroaryl radical which is unsubstituted or substituted; wherein all radicals R1 with the exception of hydrogen can additionally be substituted by a group having a —O—C-bond or a —O—Si-bond which cleaves upon the action of an acid; R′1 is for example phenylene, naphthylene, diphenylene or oxydiphenylene, wherein these radicals are unsubstituted or substituted; R2 is halogen or C1-C10haloalkyl; R3 is for example C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, wherein the groups are unsubstituted or substituted, or R3 is e.g.Type: GrantFiled: March 23, 2000Date of Patent: July 17, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Toshikage Asakura, Hitoshi Yamato, Masaki Ohwa, Jean-Luc Birbaum, Kurt Dietliker, Junichi Tanabe
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Patent number: 6210859Abstract: This invention relates to a copolymer for the manufacture of chemical amplified photoresist and a chemical amplified positive photoresist composition comprising a copolymer for the manufacture of chemical amplified photoresist as a base resin, as represented by the following formula 1, an acid generator and additive, Wherein, R1, R2, R3 and R4 are independently a hydrogen atom or a lower alkyl group; R5, R6, R7 and R8 are a hydrogen atom, an alkyl group of C1-8, an alkoxy group, an alkoxycarbonyl group or a halogen atom; h and i are independently an integer of 0-8; k, l, m and n represent an integer of element units provided that 0.3<k/(k+l+m+n)<0.9, 0≦l/(k+l+m+n)<0.6, 0≦m/(k+l+m+n)<0.6, and 0.01<n/(k+l+m+n)<0.Type: GrantFiled: October 15, 1999Date of Patent: April 3, 2001Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Hyun Pyo Jeon, Seong Ju Kim, Joo Hyeon Park, Jong Bum Lee
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Patent number: 6197475Abstract: There is disclosed a positive type photosensitive resin composition which comprises an alkali-soluble polymer (A) having a carboxyl group and/or a phenolic hydroxyl group, and a compound (B) which forms an amine compound with irradiation of light.Type: GrantFiled: April 28, 1994Date of Patent: March 6, 2001Assignee: Hitachi Chemical Co., Ltd.Inventors: Hideo Hagiwara, Makoto Kaji, Yasunori Kojima
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Patent number: 6183934Abstract: A negative photosensitive resin composition, which comprises a thermosetting polymer precursor which can be cured through cyclodehydration upon heating, and a photosensitive heat cure accelerator. This photosensitive heat cure accelerator may be, a compound having a protective substituent group which can be eliminated upon irradiation of light, an N-oxide compound which is capable of exhibiting a heat cure accelerating property through a transition of an oxide group thereof upon irradiation of light, or a compound which is capable of exhibiting a heat cure accelerating property through generation of an acid upon irradiation of light. Further, this photosensitive heat cure accelerator may be formed of a combination of a latent heat cure accelerator which is capable of changing into a compound exhibiting a heat cure accelerating property through a reaction with an acid and a photo-acid generating agent which is capable of generating an acid upon irradiation of light.Type: GrantFiled: July 1, 1998Date of Patent: February 6, 2001Assignee: Kabushiki Kaisha ToshibaInventor: Yoshiaki Kawamonzen
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Patent number: 6180313Abstract: Disclosed is a poly(disulfonyl diazomethane) compound as a class of novel compounds represented by the general formula R-SO2-C(N2)-SO2&Brketopenst; Z-SO2-C(N2)-SO2&Brketclosest; nR in which the subscript n is 1 to 5, each R is a monovalent hydrocarbon group and Z is a divalent hydrocarbon group. The invention also discloses a chemical-amplification positive-working photoresist composition which comprises the above mentioned poly(disulfonyl diazomethane) compound as the radiation-sensitive acid-generating agent in combination with a film-forming resin capable of being imparted with increased solubility in an aqueous alkaline solution by the interaction with an acid, such as a polyhydroxystyrene resin of which a part of the hydroxyl groups are substituted by acid-dissociable solubility-reducing groups, e.g., tert-butoxycarbonyl groups.Type: GrantFiled: August 27, 1999Date of Patent: January 30, 2001Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroto Yukawa, Waki Ohkubo, Kouki Tamura
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Patent number: 6159665Abstract: Photoacid generators advantageous for use in applications such as photoacid generators used in chemically amplified resists are disclosed. These compounds are based on an ortho nitro benzyl configuration employing an .alpha. substituent having high bulk, steric characteristics, and electron withdrawing ability. The enhanced efficacy is particularly found in compounds both having a suitable .alpha. substituent and a second ortho substituent with large electron withdrawing and steric effects.Type: GrantFiled: June 17, 1993Date of Patent: December 12, 2000Assignee: Lucent Technologies Inc.Inventors: Evelyn Chin, Francis Michael Houlihan, Omkaram Nalamasu
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Patent number: 6120977Abstract: An exposure technique which accomplishes high transparency and the prevention of influence of reflected light in the ultraviolet region of KrF excimer laser light, the technique being capable of decreasing reflected light by employing a base polymer having high transparency in the ultraviolet region and by employing a bleaching agent in combination with a photo acid generator, the bleaching agent being capable of preventing the formation of eaves in an upper portion of a resist pattern.Type: GrantFiled: April 3, 1996Date of Patent: September 19, 2000Assignee: Fujitsu LimitedInventors: Yuko Kaimoto, Satoshi Takechi, Akira Oikawa
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Patent number: 6114092Abstract: A photosensitive resin composition for photoresist which is highly sensitive and can directly form an image using a laser is disclosed. Said composition comprises (A) an unsaturated resin having carboxyl group(s) which is obtained by firstly reacting 0.8 to 1.3 moles of an ethylenic unsaturated monocarboxylic acid with 1 mole of an epoxy group of a homopolymer or copolymer of ethylenic unsaturated monomer having an epoxy group to obtain an unsaturated resin which is then reacted with a dibasic acid anhydride, (B) ethylenic unsaturated compound without epoxy group, and (C) photopolymerization initiator.Type: GrantFiled: September 29, 1998Date of Patent: September 5, 2000Assignee: Kansai Paint Co., Ltd.Inventors: Kenji Miyagawa, Kenji Seko
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Patent number: 6096483Abstract: The present invention provides a curable composition which comprises (A) a base-generating substance which generates a base when exposed to the action of ultraviolet light, (B) a siloxane polymer which has silicon-hydrogen bonds (Si--H) capable of reacting with hydroxy groups under the effect of the base to form silicon-oxygen bonds (Si--O) and hydrogen molecules (H.sub.2), and (C) an acid substance. This composition is cured by irradiation with ultraviolet light. During this ultraviolet irradiation, a mask is placed between a coating film of the composition and the radiation source, and the uncured portions of the composition are dissolved and removed so that a pattern is formed. The residual portions are then heated to produce a pattern-cured product.Type: GrantFiled: March 31, 1997Date of Patent: August 1, 2000Assignee: Dow Corning Asia, Ltd.Inventors: Brian R. Harkness, Mamoru Tachikawa, Kasumi Takei
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Patent number: 6054251Abstract: The present invention provides a visible laser-curable resist composition which contains at least one radical-protecting compound selected from a phosphorous acid ester compound and an aromatic compound having N,N-dimethylamino group bonded to the carbon atom forming the aromatic ring and which is free from the hindrance of curing caused by deactivation of radical by oxygen and has excellent curability, and a process for formation of a resist pattern using the above composition.Type: GrantFiled: September 25, 1997Date of Patent: April 25, 2000Assignee: Kansai Paint Co., Ltd.Inventors: Genji Imai, Hideo Kogure
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Patent number: 6051367Abstract: A photopolymerizable composition which comprises a compound having one or more addition-polymerizable ethylenically unsaturated bonds and a specific oxime ether compound. The photopolymerizable composition has high sensitivity to actinic rays in a wide region, ranging from ultraviolet to visible light, and gives a photosensitive material which has improved film strength in exposed areas.Type: GrantFiled: February 23, 1998Date of Patent: April 18, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuto Kunita, Tatsuji Higashi
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Patent number: 6051366Abstract: A visible radiation sensitive composition is described which comprises a binder, one or more polymerizable compounds containing at least one polymerizable group, and one or more dyes having an absorption range in the emission range of the radiation source, characterized in that said composition comprises as an initiator an initiator system consisting of a metallocene as a photoinitiator and an onium compound as a coinitiator. The visible radiation sensitive composition shows an increased radiation sensitivity compared to the known radiation sensitive compositions and is especially suitable for recording materials such as printing plates, which can, in particular, also be exposed by means of laser radiation in the visible range.Type: GrantFiled: May 25, 1995Date of Patent: April 18, 2000Assignee: Kodak Polychrome Graphics LLCInventors: Harald Baumann, Hans-Joachim Timpe, Hans-Peter Herting
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Patent number: 6042988Abstract: The present invention provides a chemical-amplification-type negative resist composition containing an alkali-soluble resin, a compound capable of generating an acid by irradiation and a crosslinking agent, and the resist composition of the present invention is characterized in that it further contains an organic carboxylic acid compound as an acidic compound and an organic amine compound as an alkaline compound.Type: GrantFiled: September 29, 1998Date of Patent: March 28, 2000Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Mitsuro Sato, Katsumi Oomori, Etsuko Iguchi, Kiyoshi Ishikawa, Fumitake Kaneko, Yoshiki Sugeta
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Patent number: 6025112Abstract: A photocurable composition comprises an unsaturated group-containing compound as a base material, a metal arene compound as a photopolymerization initiator and an aniline compound as a photosensitizer. As the photosensitizer aniline compound, any one or both of 2,6-diisopropyl-N,N-dimethylaniline and 2,4,6,N,N-pentamethylaniline is/are used.Type: GrantFiled: February 4, 1997Date of Patent: February 15, 2000Assignee: Brother Kogyo Kabushiki KaishaInventor: Masashi Tsuda
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Patent number: 6022666Abstract: Disclosed are novel high-sensitivity positive- and negative-working chemical-sensitization photoresist compositions capable of giving a highly heat-resistant patterned resist layer of high resolution having excellently orthogonal cross sectional profile without being influenced by standing waves. The composition contains, as an acid generating agent by irradiation with actinic rays, a specific cyano-substituted oximesulfonate compound such as .alpha.-(methylsulfonyloxyimino)-4-methoxybenzyl cyanide. The advantages obtained by the use of this specific acid-generating agent is remarkable when the film-forming resinous ingredient has such a molecular weight distribution that the ratio of the weight-average molecular weight to the number-average molecular weight does not exceed 3.5.Type: GrantFiled: January 26, 1999Date of Patent: February 8, 2000Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Hiroyuki Yamazaki, Yoshiki Sugeta, Hiroshi Komano
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Patent number: 6017675Abstract: The invention relates to the use of oximesulfonic acid esters of formula I ##STR1## m is 0 or 1 and x is 1 or 2; R.sub.1 is, for example, substituted phenyl, R.sub.2 has, for example, one of the meanings of R.sub.1 or is unsubstituted phenyl, C.sub.1 -C.sub.6 alkanoyl, unsubstituted or substituted benzoyl, C.sub.2 -C.sub.6 alkoxycarbonyl or phenoxycarbonyl; or R.sub.1 and R.sub.2, if necessary together with the CO group, form a ring, R.sub.3, when x is 1, is, for example, C.sub.1 -C.sub.18 alkyl, phenyl or phenanthryl, the radicals phenyl and phenanthryl being unsubstituted or substituted, or R.sub.3, when x is 2, is, for example, C.sub.2 -C.sub.12 alkylene, phenylene or oxydiphenylene, the radicals phenylene and oxydiphenylene being unsubstituted or substituted, as latent acid donors, especially at wavelengths over 390 nm, and to the use of the compounds in the production of photoresists.Type: GrantFiled: October 28, 1996Date of Patent: January 25, 2000Assignee: Ciba Specialty Chemials CorporationInventors: Kurt Dietliker, Martin Kunz