Radiation-activated Cross-linking Agent Containing Patents (Class 430/927)
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Patent number: 6630281Abstract: Photoresist compositions for a Top-surface Imaging Process by Silylation (TIPS), and a process for forming a positive pattern according to the TIPS using the same. The photoresist composition for the TIPS comprises a cross-linker of following Formula 1 or 2. A protecting group of the cross-linker and a hydroxyl group of the photoresist polymer are selectively crosslinked in the exposed region, and the residual hydroxyl group reacts to a silylating agent in the non-exposed region by silylation. Thus, the non-exposed region only remains after the dry-development, thereby forming a positive pattern. In addition, the photoresist composition of the present invention is suitable for the TIPS lithography using light sources such as ArF (193 nm), VUV (157 nm) and EUV (13 nm). wherein, R1, R2, R3, R4, R5, R6 and R7 are as defined in the specification.Type: GrantFiled: July 10, 2001Date of Patent: October 7, 2003Assignee: Hynix Semiconductor Inc.Inventors: Cha Won Koh, Geun Su Lee, Ki Ho Baik
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Patent number: 6623907Abstract: A positive-tone radiation-sensitive resin composition comprising: (A) a low molecular weight compound having at least one amino group in which the nitrogen atom has at least one hydrogen atom bonded thereto and at least one of the hydrogen atoms is replaced by a t-butoxycarbonyl group, (B) a photoacid generator, and (C-1) a resin insoluble or scarcely soluble in alkali which is protected by an acid-dissociable group and becomes soluble in alkali when the acid-dissociable group dissociates or (C-2) an alkali-soluble resin and an alkali solubility control agent is disclosed. Also disclosed is a negative-tone radiation-sensitive resin composition comprising the low molecular weight compound (A), the photoacid generator (B), an alkali-soluble resin (D), and a compound capable of crosslinking with the alkali-soluble resin in the presence of an acid(E).Type: GrantFiled: February 1, 2001Date of Patent: September 23, 2003Assignee: JSR CorporationInventors: Jun Numata, Aki Suzuki, Hiromichi Hara, Norihiro Natsume, Kiyoshi Murata, Masafumi Yamamoto, Akimasa Soyano, Toru Kajita, Tsutomu Shimokawa
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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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Publication number: 20030091926Abstract: A dry film photoresist having a glass transition temperature (Tg) above room temperature. The dry film photoresist is tack free. An artwork may be placed directly on the photoresist without concern that the artwork may stick to the dry film photoresist or become contaminated with photoresist. The dry film photoresist may be laminated on a support sheet and wound into a roll without concern that the photoresist will stick to the backside of the support sheet. The dry film photoresist also has reduced cold flow problems.Type: ApplicationFiled: December 11, 2002Publication date: May 15, 2003Applicant: Shipley Company, L.L.C.Inventor: James G. Shelnut
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Patent number: 6544717Abstract: Disclosed is a novel undercoating solution for the formation of an antireflection undercoating layer to intervene between the surface of a substrate and a photoresist layer to be patterned in the manufacturing process of semiconductor devices with an object to prevent adverse influences of the light reflecting at the substrate surface on the cross sectional profile of the patterned resist layer.Type: GrantFiled: March 13, 2001Date of Patent: April 8, 2003Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takako Hirosaki, Etsuko Iguchi, Masakazu Kobayashi
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Publication number: 20030039921Abstract: A chemically amplified negative photoresist composition is used for the formation of thick films having a thickness of 20 to 150 &mgr;m and includes (A) an alkali-soluble resin, (B) a compound which generates an acid upon irradiation with active light or radiant ray, and (C) a compound which serves as a crosslinking agent in the presence of an acid. The alkali-soluble resin (A) includes (a1) a novolak resin having a weight average molecular weight of from 5000 to 10000, and (a2) a polymer containing at least a hydroxystyrene constitutional unit and having a weight average molecular weight of less than or equal to 5000.Type: ApplicationFiled: July 15, 2002Publication date: February 27, 2003Applicant: TOKYO OHKA KOGYO CO., LTD.Inventors: Yasushi Washio, Koji Saito, Toshiki Okui, Hiroshi Komano
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Patent number: 6511783Abstract: A chemical amplification system negative resist composition for an electron beam and/or an X-ray, which is excellent in sensitivity and resolution and has a rectangular profile, comprising an alkali-soluble resin, a radiation-sensitive acid generator and a crosslinking agent which initiates crosslinking by an acid, in which the crosslinking agent is a phenol derivative having 3 to 5 benzene ring atomic groups in a molecule, having a molecular weight of 1,200 or less, and having two or more hydroxymethyl and/or alkoxymethyl groups in all in the molecule, the groups being combined with at least any of the benzene ring atomic groups.Type: GrantFiled: August 10, 2000Date of Patent: January 28, 2003Assignee: Fuji Photo Film Co., Ltd.Inventor: Kazuya Uenishi
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Patent number: 6458525Abstract: A method for preparing a photothermographic material comprising an organic silver salt is disclosed, comprising a step of treating the organic silver salt under a gas atmosphere containing an inert gas having a volume fraction of not less than 85% or under a gas atmosphere containing oxygen gas having a volume fraction of not more than 15%. Packaging the photothermographic material under the inert gas atmosphere is also disclosed.Type: GrantFiled: November 3, 2000Date of Patent: October 1, 2002Assignee: Konica CorporationInventors: Hideki Takiguchi, Hitoshi Adachi, Hideki Hoshino, Shu Nishiwaki
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Patent number: 6455231Abstract: Dry film resists of the invention in general comprise a photoactive component, a highly viscous or solid (at room temperature, ca. 25° C.) crosslinker component, and preferably a flexibilizing agent. Preferred dry film constructions of the invention do not require the use of a protective cover sheet due to the composition's very dry nature.Type: GrantFiled: November 3, 1999Date of Patent: September 24, 2002Assignee: Shipley Company, L.L.C.Inventor: James G. Shelnut
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Patent number: 6432614Abstract: There is provided a photosensitive resin composition comprising: a copolymer resin; a bifunctional or higher polyfunctional photopolymerizable acrylate monomer; an epoxy resin; and an initiator, the copolymer resin comprising 5 to 55% by mole of constituent units represented by formula (1) and 5 to 95% by mole of constituent units represented by formula (2), the constituent units represented by formula (1) having been partially reacted, through carboxyl groups thereof, with a (meth)acryloylalkyl isocyanate compound, the constituent units represented by formula (2) having been partially reacted, through hydroxyl groups thereof, with a (meth)acryloylalkyl isocyanate compound, the copolymer resin containing 5 to 95% by mole of (meth)acryloyl groups and having an acid value of 5 to 400 mg KOH/g and a weight average molecular weight of 10,000 to 1,000,000 as determined using polystyrene as a standard: wherein R represents hydrogen or an alkyl group having 1 to 5 carbon atoms and R1 represents anType: GrantFiled: July 30, 1999Date of Patent: August 13, 2002Assignee: Dai Nippon Printing Co., Ltd.Inventors: Kenji Ueda, Satoshi Shioda, Hirotaka Nishijima, Tomoaki Mukaiyama, Syuichi Mitsuhashi
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Publication number: 20020076644Abstract: A photo-curable composition comprising (a) an elastomeric component containing one or more unsaturated, high molecular weight, endgroup-modified polymers; (b) a photopolymerization initiating system; optionally (c) one or more cross-linking agents; and optionally (d) other additives. Photo-curable compositions of the present invention exhibit faster cross-linking (i.e., curing) rates (i.e., lower minimum exposure times) than similar compositions containing no endgroup-modified polymers. Cured compositions of the present invention exhibit lower solvent swell, and similar or increased softness (i.e., lower hardness as measured by Shore A hardness) when compared to cured compositions containing no unsaturated, high molecular weight, endgroup-modified polymers.Type: ApplicationFiled: December 7, 2001Publication date: June 20, 2002Inventors: Andre J. Uzee, Calvin P. Esneault, Michael O. Myers
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Patent number: 6406829Abstract: Disclosed is a novel negative-working chemical-amplification photoresist composition comprising (A) an alkali-soluble resin, (B) an acid-generating agent and (C) a crosslinking agent, of which the component (B) is an onium salt compound having a specific fluoroalkyl sulfonate ion as the anionic moiety and the component (C) is a specific ethyleneurea compound substituted for at least one nitrogen atom by a hydroxymethyl or alkoxymethyl group. The photoresist composition is particularly suitable for the formation of a photoresist layer on a substrate surface provided with an undercoating of a water-insoluble organic anti-reflection film exhibiting excellent pattern resolution and orthogonal cross sectional profile of the patterned resist layer with a good temperature latitude in the post-exposure baking treatment for latent image formation.Type: GrantFiled: August 15, 2000Date of Patent: June 18, 2002Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Toshikazu Tachikawa, Fumitake Kaneko, Naotaka Kubota, Miwa Miyairi, Takako Hirosaki, Koutaro Endo
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Publication number: 20020061467Abstract: Disclosed is a novel negative-working chemical-amplification photoresist composition comprising (A) an alkali-soluble resin, (B) an acid-generating agent and (C) a crosslinking agent, of which the component (B) is an onium salt compound selected from the group consisting of iodonium salt compounds and sulfonium salt compounds, having a specific fluoroalkyl sulfonate ion as the anionic moiety and the component (C) is a specific ethyleneurea compound substituted for at least one nitrogen atom by a hydroxymethyl or alkoxymethyl group. The photoresist composition is particularly suitable for the formation of a photoresist layer on a substrate surface provided with an undercoating of a water-insoluble organic anti-reflection film exhibiting excellent pattern resolution and orthogonal cross sectional profile of the patterned resist layer with a good temperature latitude in the post-exposure baking treatment for latent image formation.Type: ApplicationFiled: January 24, 2002Publication date: May 23, 2002Inventors: Toshikazu Tachikawa, Fumitake Kaneko, Naotaka Kubota, Miwa Miyairi, Takako Hirosaki, Koutaro Endo
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Patent number: 6391516Abstract: The present invention discloses an imaging element comprising on a hydrophilic surface of a lithographic base an image forming layer comprising hydrophobic thermoplastic polymer particles dispersed in a hydrophilic binder and (ii) a compound capable of converting light to heat, said compound being comprised in said image forming layer or a layer adjacent thereto, characterised in that said image forming layer further comprises a cross-linking agent capable of cross-linking said hydrophilic binder upon heating in a ratio between 1:100 and 200:1 by weight versus the hydrophilic binder. The present invention further provides a method for making a printing plate therewith. According to this method, the above imaging element is preferably exposed by means of a laser and is subsequently developed with plain water or an aqueous liquid.Type: GrantFiled: November 8, 1996Date of Patent: May 21, 2002Assignee: Agfa-GevaertInventors: Joan Vermeersch, Marc Van Damme
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Publication number: 20020045127Abstract: Polyimide is produced by reacting two kinds of diamine compounds consisting of diaminopolysiloxane and a carboxyl group-containing diamine or three kinds of diamine compounds consisting of diaminopolysiloxane, a carboxyl group-containing diamine and an aromatic or alicyclic diamine with a dicarboxylic acid anhydride having a 2,5-dioxotetrahydrofuryl group as one acid anhydride group, thereby once forming a polyamic acid, and subjecting the polyamic acid to polyimidization reaction. The resulting polyimide itself is soluble in low boiling organic solvents for general purpose use, typically methyl ethyl ketone. A photosensitive composition comprising the polyimide, a photo crosslinking agent and a photo acid-generating agent forms a negative type polyimide pattern upon development with an aqueous alkali solution.Type: ApplicationFiled: October 18, 2001Publication date: April 18, 2002Inventors: Lin-Chiu Chiang, Jenq-Tain Lin, Nobuyuki Sensui
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Patent number: 6365324Abstract: Polyimide is produced by reacting two kinds of diamine compounds consisting of diaminopolysiloxane and a carboxyl group-containing diamine or three kinds of diamine compounds consisting of diaminopolysiloxane, a carboxyl group-containing diamine and an aromatic or alicyclic diamine with a 4,4′-(hexafluoroisopropylidene)diphthalic acid dianhydride, thereby once forming a polyamic acid, and subjecting the polyamic acid to polyimidization reaction. The resulting polyimide itself is soluble in low boiling organic solvents for general purpose use, typically methyl ethyl ketone. A photosensitive composition comprising the polyimide, a photo crosslinking agent and a photo acid-generating agent forms a negative type polyimide pattern upon development with an aqueous alkali solution.Type: GrantFiled: March 26, 1999Date of Patent: April 2, 2002Assignee: Nippon Mektron, LimitedInventors: Lin-chiu Chiang, Jenq-Tain Lin, Nobuyuki Sensui
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Patent number: 6333133Abstract: A positive planographic printing material which is capable of recording a digital data from a computer and the like, using a solid laser or a semiconductor laser emitting infrared rays. The positive planographic printing material comprises at least the following components (A) to (C): (A) a polyfunctional amine compound, (B) a polymer which is water-insoluble and aqueous alkali solution-soluble and (C) an infrared absorber.Type: GrantFiled: February 14, 2000Date of Patent: December 25, 2001Assignee: Fuji Photo Film Co., Ltd.Inventors: Ippei Nakamura, Kazuto Kunita
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Publication number: 20010053496Abstract: Compositions and methods of the invention provide for a controlled flow of resist into device contact (via) holes during a post-exposure, post-development hard-bake step. Resists of the invention are positive-acting and contain one or more components that are preferably substantially stable (i.e. no substantial crosslinking) during: 1) soft-bake, pre-exposure thermal treatment to remove solvent carrier of the applied resist, and 2) post-exposure, pre-development thermal treatment to promote or enhance the acid-promoted reaction in exposed regions (typically a de-blocking reaction). However, resists of the invention will crosslink during a post-development more stringent thermal treatment (thermal flow hard-bake step).Type: ApplicationFiled: April 3, 2001Publication date: December 20, 2001Applicant: Shipley Company, L.L.C.Inventor: Timothy G. Adams
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Patent number: 6322949Abstract: A positive-tone or negative-tone radiation sensitive resin composition comprising (A) a photoacid generator represented by the following formula (1-1) or (1-2): wherein R1, R2, R5, and R6 are an alkyl group , R3 and R7 are a hydroxyl group or —OR4 (wherein R4 is an organic group), A1− and A2− indicate a monovalent anion, a and c denote an integer of 4-7, and b and d an integer of 0-7. The positive-tone resin composition further comprises (B1) an acid-cleavable group-containing resin or (B2) an alkali-soluble resin and an alkali solubility control agent, and the negative-tone radiation sensitive resin composition further comprises (C) an alkali-soluble resin and (D) a crosslinking agent. The resin compositions are highly sensitive and exhibit superior resolution and pattern forming performance.Type: GrantFiled: December 20, 2000Date of Patent: November 27, 2001Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Mitsuhito Suwa, Haruo Iwasawa, Toru Kajita, Shin-ichiro Iwanaga
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Patent number: 6322948Abstract: The present invention is directed to photoresist cross-linkers selected from the group consisting of a cross-linker monomer represented by following Chemical Formula 1, and homopolymers and copolymers thereof. Such cross-linkers are suitable for use in photolithography processes employing KrF (248 nm), ArF (193 nm), E-beam, ion-beam or EUV light sources.Type: GrantFiled: February 7, 2000Date of Patent: November 27, 2001Assignee: Hyundai Electronics Industries Co., Ltd.Inventors: Jae Chang Jung, Keun Kyu Kong, Jin Soo Kim, Ki Ho Baik
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Patent number: 6319650Abstract: An improved, aqueous base developable, high resolution photoresist composition for use in deep UV and compatable with high base strength aqueous developers is disclosed. The composition of the present invention comprises of a phenolic functional methacrylate polymer resin, a crosslinker selected from glycoluril derivatives capable of reacting with there resins under acid catalysis, a photoacid generator and an organic solvent. The composition of the present invention is particularly useful for production of negative tone images of high resolution (less than 0.125 micrometer).Type: GrantFiled: February 25, 2000Date of Patent: November 20, 2001Assignee: International Business Machines CorporationInventors: Jeffrey Donald Gelorme, Ali Afzali-Ardakani, Teresita Ordonez Graham, Laura Louise Kosbar
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Publication number: 20010036590Abstract: A negative-working chemical amplification-type resist composition for electron beams or X-rays satisfying the characteristics of the sensitivity and resolution•resist pattern for the use of electron beams or X-rays is provided. The chemical amplification-type negative-working resist composition contains (1) an alkali-soluble resin having a weight-average molecular weight of exceeding 3,000 and not larger than 1,000,000, (2) a crosslinking agent causing crosslinkage by an acid, and (3) a compound generating an acid by the irradiation of electron beams or X-rays, wherein the alkali-soluble resin has a specific structure.Type: ApplicationFiled: December 18, 2000Publication date: November 1, 2001Inventor: Yutaka Adegawa
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Patent number: 6309799Abstract: The invention relates to a process for producing a printing form, in which a covering layer (5) is applied to a first radiation-sensitive layer (4) arranged on a carrier (1), the applied covering layer (5) is structured in accordance with a pattern to be printed, in order to form an irradiation mask (5′), and the radiation-sensitive layer (4) is irradiated and developed. In this way, in the production of printing forms, an irradiation mask (5′) can be applied very precisely in accordance with a pattern to be printed later.Type: GrantFiled: November 3, 1998Date of Patent: October 30, 2001Assignee: Schablonentechnik Kufstein AktiengesellschaftInventor: Siegfried Rückl
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Publication number: 20010026901Abstract: There are here disclosed a photoresist material for lithography using a light of 220 nm or less which comprises at least a polymer represented by the following formula (2) and a photo-acid generator for generating an acid by exposure: 1Type: ApplicationFiled: December 29, 2000Publication date: October 4, 2001Inventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
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Publication number: 20010024759Abstract: A photo-curable composition comprising (a) an elastomeric component containing one or more unsaturated, high molecular weight, endgroup-modified polymers; (b) a photopolymerization initiating system; optionally (c) one or more cross-linking agents; and optionally (d) other additives. Photo-curable compositions of the present invention exhibit faster cross-linking (i.e., curing) rates (i.e., lower minimum exposure times) than similar compositions containing no endgroup-modified polymers. Cured compositions of the present invention exhibit lower solvent swell, and similar or increased softness (i.e., lower hardness as measured by Shore A hardness) when compared to cured compositions containing no unsaturated, high molecular weight, endgroup-modified polymers.Type: ApplicationFiled: May 4, 2001Publication date: September 27, 2001Inventors: Andre J. Uzee, Michael O. Myers, Calvin P. Esneault
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Publication number: 20010023050Abstract: A positive-tone radiation-sensitive resin composition comprising: (A) a low molecular weight compound having at least one amino group in which the nitrogen atom has at least one hydrogen atom bonded thereto and at least one of the hydrogen atoms is replaced by a t-butoxycarbonyl group, (B) a photoacid generator, and (C-1) a resin insoluble or scarcely soluble in alkali which is protected by an acid-dissociable group and becomes soluble in alkali when the acid-dissociable group dissociates or (C-2) an alkali-soluble resin and an alkali solubility control agent is disclosed. Also disclosed is a negative-tone radiation-sensitive resin composition comprising the low molecular weight compound (A), the photoacid generator (B), an alkali-soluble resin (D), and a compound capable of crosslinking with the alkali-soluble resin in the presence of an acid(E).Type: ApplicationFiled: February 1, 2001Publication date: September 20, 2001Inventors: Jun Numata, Aki Suzuki, Hiromichi Hara, Norihiro Natsume, Kiyoshi Murata, Masafumi Yamamoto, Akimasa Soyano, Toru Kajita, Tsutomu Shimokawa
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Patent number: 6284428Abstract: Disclosed is a novel undercoating solution for the formation of an antireflection undercoating layer to intervene between the surface of a substrate and a photoresist layer to be patterned in the manufacturing process of semiconductor devices with an object to prevent adverse influences of the light reflecting at the substrate surface on the cross sectional profile of the patterned resist layer. The undercoating composition is a uniform solution which comprises: (A) a nitrogen-containing organic compound having, in a molecule, at least two amino groups substituted by at least one substituent group selected from the group consisting of hydroxyalkyl groups and alkoxyalkyl groups such as an N,N-substituted benzoguanamine compound; (B) an organic acid or an inorganic acid of which the acid residue contains at least one atom of sulfur such as methanesulfonic acid and dodecylbenzene sulfonic acid; and (C) an organic solvent such as propyleneglycol monomethyl ether.Type: GrantFiled: January 28, 2000Date of Patent: September 4, 2001Assignee: Tokyo Ohka Kogyo Co., Ltd,Inventors: Takako Hirosaki, Etsuko Iguchi, Masakazu Kobayashi
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Photoresist compositions with pendant polar-functionalized aromatic groups and acid-labile branching
Patent number: 6265134Abstract: Acid-catalyzed positive photoresist compositions having generally improved performance (especially photoresist compositions having improved contrast (solubility differential), shrinkage and processing kinetics on radiation exposure) are obtained by use of polymers containing pendant polar-functionalized aromatic groups and acid-labile light crosslinking. The photoresist compositions also may contain a photosensitive acid-generating component as well as a solvent and possibly other auxiliary components. The polymers may contain other functional groups or components designed to impart alkaline-solubility, to provide alkaline-solubility protection in the absence of generated acid, etc. The photoresist compositions can be used to create patterned photoresist structures and further to make conductive, semiconductive or insulative structures by photolithography.Type: GrantFiled: October 30, 2000Date of Patent: July 24, 2001Assignee: International Business Machines CorporationInventors: Pushkara R. Varanasi, Ahmad D. Katnani, Mahmoud M. Khojasteh, Ranee W. Kwong -
Publication number: 20010006758Abstract: A negative radiation-sensitive resin composition including (A) an alkali-soluble resin containing a copolymer selected from the group consisting of a hydroxystyrene/styrene copolymer having hydroxystyrene units in a content of from 65 to 90 mol % and a hydroxystyrene/&agr;-methylstyrene copolymer having hydroxystyrene units in a content of from 65 to 90 mol %, (B) a radiation-sensitive acid-generating agent containing a hydroxyl group-containing onium salt compound, and (C) a cross-linking agent containing an N-(alkoxymethyl)glycoluril compound. The composition is suitable as a chemically amplified negative resist, to which alkaline developing solutions having usual concentration are applicable and which can form, in usual line-and-space patterns, resist patterns having a rectangular cross-sectional shape in a high resolution and also has superior sensitivity, developability and dimensional fidelity.Type: ApplicationFiled: December 21, 2000Publication date: July 5, 2001Inventors: Toshiyuki Kai, Yong Wang, Shirou Kusumoto, Yoshihisa Ohta
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Publication number: 20010004510Abstract: Novel silicon-containing polymer compounds, based on cyclic olefins. These polymer compounds can be used as photoresist materials and because they are transparent to radiation in the spectral range from 193 to 13 nm, which is highly energetic and strongly attenuated, are particularly advantageous as refractory bilayer photoresist materials for semiconductor wafer patterning processes that employ deep ultraviolet (DUV) and extreme ultraviolet (EUV) radiation.Type: ApplicationFiled: December 19, 2000Publication date: June 21, 2001Inventor: David R. Wheeler
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Patent number: 6245484Abstract: Polyimide is produced by reacting two kinds of diamine compounds consisting of diaminopolysiloxane and a carboxyl group-containing diamine or three kinds of diamine compounds consisting of diaminopolysiloxane, a carboxyl group-containing diamine and an aromatic or alicyclic diamine with a dicarboxylic acid anhydride having a 2,5-dioxotetrahydrofuryl group as one acid anhydride group, thereby once forming a polyamic acid, and subjecting the polyamic acid to polyimidization reaction. The resulting polyimide itself is soluble in low boiling organic solvents for general purpose use, typically methyl ethyl ketone. A photosensitive composition comprising the polyimide, a photo crosslinking agent and a photo acid-generating agent forms a negative type polyimide pattern upon development with an aqueous alkali solution.Type: GrantFiled: February 1, 2000Date of Patent: June 12, 2001Assignee: Nippon Mektron LimitedInventors: Lin-chiu Chiang, Jenq-Tain Lin, Nobuyuki Sensui
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Patent number: 6232039Abstract: Polyimide is produced by reacting two kinds of diamine compounds consisting of diaminopolysiloxane and a carboxyl group-containing diamine or three kinds of diamine compounds consisting of diaminopolysiloxane, a carboxyl group-containing diamine and an aromatic or alicyclic diamine with a 4,4′-(hexafluoroisopropylidene)diphthalic acid dianhydride, thereby once forming a polyamic acid, and subjecting the polyamic acid to polyimidization reaction. The resulting polyimide itself is soluble in low boiling organic solvents for general purpose use, typically methyl ethyl ketone. A photosensitive composition comprising the polyimide, a photo crosslinking agent and a photo acid-generating agent forms a negative type polyimide pattern upon development with an aqueous alkali solution.Type: GrantFiled: January 28, 2000Date of Patent: May 15, 2001Assignee: Nippon Mektron LimitedInventors: Lin-chiu Chiang, Jenq-Tain Lin, Nobuyuki Sensui
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Patent number: 6200726Abstract: A photo resist composition contains at least one photoacid generator (PAG), wherein at least two photoacids are produced upon exposure of the photo resist to actinic energy and wherein the photo resist is capable of producing a hybrid response. The function of providing generation of two photoacids in a hybrid resist is to optimize the use of hybrid resist by varying the hybrid space width. The at least two photoacids may differ in their effectiveness at catalyzing at least one mechanism of the hybrid response. In particular, one photoacid may be a weaker acid and another may be a stronger acid, wherein there exists a difference of at least four orders of magnitude between the acid dissociation constant (Ka) of the weaker acid and the stronger acid.Type: GrantFiled: October 13, 1998Date of Patent: March 13, 2001Assignee: International Business Machines CorporationInventors: Kuang-Jung Chen, Steven J. Holmes, Wu-Song Huang, Ahmad D. Katnani, Paul A. Rabidoux
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Patent number: 6136498Abstract: A photoresist composition for use in lithographic processes in the fabrication of semiconductor devices such as integrated circuit structures is disclosed. The photoresist composition includes a monomeric sensitizer bounding to a base-soluble long chain polymer.Type: GrantFiled: June 28, 1996Date of Patent: October 24, 2000Assignee: International Business Machines CorporationInventors: Premlatha Jagannathan, Leo L. Linehan, Wayne M. Moreau, Randolph J. Smith
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Patent number: 6087064Abstract: Novel silsesquioxane polymers are formed by methods which avoid the use of BBr.sub.3. The novel silsesquioxane polymers are especially useful in negative photoresist compositions and photolithographic processes. Alternatively, improved silsesquioxane polymer-containing negative photoresist compositions are obtained by using a polymer component containing a blend of silsesquioxane polymer and non-silsesquioxane polymer. The photoresist compositions provide improved dissolution characteristics enabling the use of 0.26 N TMAH developer. The photoresist compositions also provide improved thermal characteristics enabling use of higher processing temperatures. The photoresist compositions are especially useful in a multilayer photolithographic processes and are capable of producing high resolution.Type: GrantFiled: September 3, 1998Date of Patent: July 11, 2000Assignee: International Business Machines CorporationInventors: Qinghuang Lin, Marie Angelopoulos, Ahmad D. Katnani, Ratnam Sooriyakumaran
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Patent number: 6083658Abstract: The negative working image recording image recording material of the present invention is a negative working image recording material comprising (A) a compound which acts as a cross-linking agent in the presence of an acid, (B) a binder polymer, (C) a compound which generates an acid by the action of heat and (D) an infrared absorber, wherein (A) the compound which acts as a cross-linking agent in the presence of an acid is a phenol derivative represented by the following general formula (I) or (II) wherein each of the groups is defined and wherein (B) the binder polymer is a polymer having in the side chain an aromatic hydrocarbon ring having directly linked thereto a hydroxyl group or an alkoxy group if (A) is a phenol derivative represented by the general formula (I), but (B) the binder polymer is a polymer having in the main chain or the side chain an aromatic hydrocarbon ring having directly linked thereto a hydroxyl group or an alkoxy group if (A) is a phenol derivative represented by the general formulType: GrantFiled: April 20, 1998Date of Patent: July 4, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuto Kunita, Keitaro Aoshima, Ippei Nakamura, Tatsuo Nakamura
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Patent number: 6077641Abstract: A lithographic printing plate precursor comprising on a support a radiation sensitive composition which comprises (1) a novolac resin, (2) a condensing agent for the novolac resin which is either a methylol polyvinyl phenol compound or a bishydroxymethyl compound, (3) a radiation sensitive latent acid generating compound, and (4) an infra-red sensitizing dye.Type: GrantFiled: July 15, 1999Date of Patent: June 20, 2000Assignee: Kodak Polychrome Graphics LLCInventors: Gareth R. Parsons, Alan S. V. Monk, Eduard Kottmair
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Patent number: 6068963Abstract: The present invention provides a negative-type image recording material which does not smudge non-image portions during printing, which provides excellent film strength of recorded image portions, and which exhibits press life. Particularly when the material is used for recording with a variety of laser devices that emit infrared rays, the material enables direct plate making from computer digital data. The negative-type image recording material of the invention contains (A) a polymer having a heterocyclic group containing an unsaturated bond therein, (B) a cross-linking agent that cross-links with the aid of an acid, and (C) a compound that generates an acid upon exposure to light or heat.Type: GrantFiled: January 16, 1998Date of Patent: May 30, 2000Assignee: Fuji Photo Film Co., Ltd.Inventor: Keitaro Aoshima
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Patent number: 6013412Abstract: The present invention provides a negative type image recording material comprising a polyurethane resin having a carboxyl group, a compound cross-linkable by an acid, and a compound generating an acid due to the application of heat or light.Accordingly, a negative type image recording material can be provided which has excellent crosslinking properties with a crosslinking agent, and consequently, excellent layer strength and good printing durability, and which enables a direct plate making from digital data.Type: GrantFiled: February 25, 1998Date of Patent: January 11, 2000Assignee: Fuji Photo Film Co., Ltd.Inventor: Keitaro Aoshima
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Patent number: 5998089Abstract: Disclosed are a photosensitive resin composition containing a fullerene and a polymer compound bearing a functional group which can react with the fullerene under irradiation of visible light; method for forming negative-type picture elements comprising steps of: forming a layer composed of the above composition, irradiating the layer with visible light through a photo mask having a pattern transmitting the visible light as a part of the mask to cure portions of the layer irradiated by the visible light, and removing uncured portions of the layer to form a resist film having cured portions of the pattern: and a method for producing devices comprising steps of: forming a layer of the above composition on an image-forming layer provided on a substrate, irradiating the layer with visible light through a photo mask having a pattern transmitting the visible light as a part of the mask to cure portions of the layer irradiated by the visible light, removing uncured portions of the layer to form a resist film havingType: GrantFiled: September 12, 1997Date of Patent: December 7, 1999Assignee: The Institute of Physical and Chemical ResearchInventors: Yusuke Tajima, Tadahiro Ishii, Kazuo Takeuchi
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Patent number: 5962191Abstract: The negative-working resist composition which comprises a (meth)acrylate copolymer comprising (a) a vinyl monomer unit which contains in a side chain thereof at least one carbon--carbon double bond which does not concern itself with any polymerization reaction, but is able to be crosslinked with a crosslinking agent, (b) an acrylamide or methacrylamide monomer unit, (c) an acrylic acid or methacrylic acid monomer unit and (d) an acrylic acid or methacrylic acid adamantyl monomer unit as well as a crosslinking agent capable of being decomposed upon exposure to a patterning radiation and then causing crosslinking of said copolymer upon heating. The resist composition is particularly suitable for excimer laser lithography using an aqueous basic solution as a developer, and the formed resist patterns can exhibit a high sensitivity and excellent dry etch resistance without swelling.Type: GrantFiled: August 12, 1998Date of Patent: October 5, 1999Assignee: Fujitsu LimitedInventors: Koji Nozaki, Ei Yano, Keiji Watanabe, Takahisa Namiki, Miwa Igarashi, Yoko Kuramitsu
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Patent number: 5958648Abstract: A radiation sensitive resin composition comprising (A) a fluorine-containing copolymer of hexafluoropropylene, at least one compound selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and an unsaturated compound (B) an acid generating compound which generates an acid upon exposure to radiation; (C) a cross-linkable compound; and (D) an organic solvent. The composition suitable is useful for a negative resist for forming a mask for the production of a circuit such as a semiconductor integrated circuit or a thin film transistor circuit for liquid crystal displays as well as a material for forming a permanent film such as an interlaminar insulating film or a color filter protective film.Type: GrantFiled: May 21, 1998Date of Patent: September 28, 1999Assignee: JSR CorporationInventors: Isao Nishimura, Masayuki Endo
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Patent number: 5952150Abstract: A positive-tone or negative-tone radiation sensitive resin composition which allows easy preparation of a resist, exhibits superior storage stability, high sensitivity, and high resolution capability, and is capable of producing excellent resist patterns. The positive-tone type composition comprises (A) a disulfonylmethane derivative in which the main chain with two sulfonyl groups bonded forms a three to eleven member cyclic carbon structure and (B) (a) a resin protected by an acid decomposable group or (b) an alkali-soluble resin and an alkali-solubility control agent. The negative-tone type composition comprises the component (A), (C) an alkali-soluble resin, and (D) a cross-linking agent.Type: GrantFiled: July 14, 1997Date of Patent: September 14, 1999Assignee: JSR CorporationInventors: Yoshihisa Ohta, Yong Wang, Takayoshi Tanabe, Shin-ichiro Iwanaga
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Patent number: 5939236Abstract: The invention provides new light absorbing crosslinking compositions suitable for use as an antireflective composition, particularly for deep UV applications. The antireflective compositions of the invention comprise a photoacid generator that is activated during exposure of an overcoated photoresist. Antireflective compositions of the invention can significantly reduce undesired footing of an overcoated resist relief image.Type: GrantFiled: February 7, 1997Date of Patent: August 17, 1999Assignee: Shipley Company, L.L.C.Inventors: Edward K. Pavelchek, Manuel DoCanto
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Patent number: 5935758Abstract: A laser-induced thermal imaging system having a donor element and a receptor element. The donor element includes a substrate on which is coated transfer material that includes: a binder including a hydroxylic resin; a fluorocarbon additive; a cationic infrared absorbing dye; a dihydropyridine latent crosslinking agent; and a dispersible material. The receptor element comprises a texturized surface.Type: GrantFiled: April 22, 1997Date of Patent: August 10, 1999Assignee: Imation Corp.Inventors: Ranjan C. Patel, Mark R. I. Chambers, Dian E. Stevenson, Jonathan C. Vogel, Kevin Kidnie, John Souter, Gregory L. Zwaldo
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Patent number: 5863699Abstract: A photosensitive composition for forming a pattern through a light-exposure with either one of ArF excimer laser and F.sub.2 excimer laser, which comprises a compound having either an acid-decomposable or acid-crosslinkable group, and a compound represented by the following general formula (1): ##STR1## wherein Ar.sup.1 and Ar.sup.2 are individually an aromatic ring or condensed aromatic ring, R.sup.1 and R.sup.2 are individually halogen atoms or monovalent organic group, X is a group selected from the group consisting of CF.sub.3 SO.sub.3, CH.sub.3 SO.sub.3, CF.sub.3 COOH, ClO.sub.4, SbF.sub.6 and AsF.sub.6, Z is a group selected from the group consisting of Cl, Br, I, S--R and Se--R (R is an alkyl group having 1 to 10 carbon atoms or perfluoroalkyl group having 1 to 10 carbon atoms), and m and n are 0 or a positive integer.Type: GrantFiled: October 9, 1996Date of Patent: January 26, 1999Assignee: Kabushiki Kaisha ToshibaInventors: Koji Asakawa, Toru Ushirogochi, Naomi Shida, Makoto Nakase
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Patent number: 5789136Abstract: Proposed is an alkali-developable negative-working photoresist composition in the form of a solution capable of exhibiting high sensitivity and greatly improved stability of the resist layer of the composition on a substrate surface after pattern-wise exposure to actinic rays and kept for a substantial length of time before further processing. The photoresist composition comprises, as the essential ingredients, (a) an alkali-soluble resin such as a copolymer of hydroxystyrene and styrene; (b) a compound capable of releasing an acid when irradiated with actinic rays such as tris(2,3-dibromopropyl) isocyanurate; (c) a crosslinking agent selected from the group consisting of melamine resins and urea resins substituted at the N-positions by methylol groups, alkoxy methyl groups or a combination thereof; and (d) a sensitivity improver which is hexa(methoxymethyl) melamine or di(methoxymethyl) urea, each in a specified proportion.Type: GrantFiled: April 5, 1996Date of Patent: August 4, 1998Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Mitsuru Sato, Katsumi Oomori, Kiyoshi Ishikawa, Etsuko Iguchi, Fumitake Kaneko
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Patent number: 5780117Abstract: Radiation-curable latex compositions having a secondary curing mechanism are disclosed. In these compositions, an anionically stabilized, water-borne dispersion of one or more radiation-curable resins is combined with a low molecular weight compound having at least two reactive functional groups, wherein one reactive functional group comprises an epoxy and the other reactive functional group comprises either an epoxy or a functionality capable of self-condensation after film formation. Also disclosed is a method for providing a cross-linked protective coating on a substrate, wherein a coating of the composition of the present invention is applied to the substrate, the coated substrate is exposed to actinic radiation to effect curing, and then the unexposed or underexposed portions of the coated substrate are allowed to cure at room temperature or greater.Type: GrantFiled: February 25, 1997Date of Patent: July 14, 1998Assignee: Rohm and Haas CompanyInventors: Andrew Joseph Swartz, Kurt Arthur Wood
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Patent number: 5780206Abstract: A resist composition for deep ultraviolet light comprising (a) one of the following resin components (i)-(iii): (i) a resin which becomes alkali-soluble by eliminating protective groups by the action of an acid, (ii) a combination of an alkali-soluble resin and a dissolution-inhibiting compound, and (iii) a combination of an alkali-soluble resin and a crosslinkable compound, (b) an acid generater, (c) a special anthracene derivative, and (d) a solvent, is suitable for forming a pattern using deep ultraviolet light, KrF excimer laser light, etc., on a highly reflective substrate having level differences due to absorption of undesirable reflected deep ultraviolet light.Type: GrantFiled: July 23, 1997Date of Patent: July 14, 1998Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.Inventors: Fumiyoshi Urano, Takanori Yasuda, Akiko Katsuyama, Kazuhiro Yamashita
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Patent number: 5695910Abstract: A resist composition for deep ultraviolet light comprising (a) one of the following resin components (i)-(iii): (i) a resin which becomes alkali-soluble by eliminating protective groups by the action of an acid, (ii) a combination of an alkali-soluble resin and a dissolution-inhibiting compound, and (iii) a combination of an alkali-soluble resin and a crosslinkable compound, (b) an acid generater, (c) a special anthracene derivative, and (d) a solvent, is suitable for forming a pattern using deep ultraviolet light, KrF excimer laser light, etc., on a highly reflective substrate having level differences due to absorption of undesirable reflected deep ultraviolet light.Type: GrantFiled: August 26, 1996Date of Patent: December 9, 1997Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electrical Industrial Co., Ltd.Inventors: Fumiyoshi Urano, Takanori Yasuda, Akiko Katsuyama, Kazuhiro Yamashita