Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
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Patent number: 6994944Abstract: A radiation sensitive resin composition for the formation of cathode separators for EL display devices which have heat resistance and adhesion required for cathode separators for EL display devices and an inversely tapered shape, cathode separators formed therefrom and an EL display device comprising the cathode separators. The radiation sensitive resin composition for the formation of cathode separators for EL display devices comprises (A) an alkali soluble resin, (B) the compound represented by the formulae (I) to (IV) and (C) a trihalomethyltriazine and/or an onium salt, the cathode separators are formed from the radiation sensitive resin composition and the EL display device comprises the cathode separators formed from the radiation sensitive resin composition.Type: GrantFiled: September 6, 2001Date of Patent: February 7, 2006Assignee: JSR CorporationInventors: Isao Nishimura, Masayoshi Suzuki, Hirofumi Sasaki, Kazuaki Niwa
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Patent number: 6994945Abstract: Novel silicon-containing polymers are obtained by copolymerizing a vinylsilane monomer with a compound having a low electron density unsaturated bond such as maleic anhydride, maleimide derivatives or tetrafluoroethylene. Using the polymers, chemical amplification positive resist compositions sensitive to high-energy radiation and having a high sensitivity and resolution at a wavelength of less than 300 nm and improved resistance to oxygen plasma etching are obtained.Type: GrantFiled: March 1, 2002Date of Patent: February 7, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takanobu Takeda, Jun Hatakeyama, Toshinobu Ishihara, Tohru Kubota, Yasufumi Kubota
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Patent number: 6994948Abstract: A photoimageable composition comprising finely divided particles of inorganic material comprising coated silver particles that are at least partially coated with at least one surfactant and inorganic binder dispersed in organic medium comprising an aqueous developable polymer, photo-initiation system and organic solvent.Type: GrantFiled: September 27, 2002Date of Patent: February 7, 2006Assignee: E.I. du Pont de Nemours and Company, Inc.Inventors: Howard David Glicksman, Haixin Yang
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Patent number: 6991890Abstract: A negative photoresist composition and a method of patterning a substrate through use of the negative photoresist composition. The composition includes: a radiation sensitive acid generator; an additive; and a resist polymer derived from at least one first monomer including a hydroxy group. The first monomer may be acidic or approximately pH neutral. The resist polymer may be further derived from a second monomer having an aqueous base soluble moiety. The additive may include one or more alicyclic structures. The acid generator is adapted to generate an acid upon exposure to radiation. The resist polymer is adapted to chemically react with the additive in the presence of the acid to generate a non-crosslinking reaction product that is insoluble in an aqueous alkaline developer solution.Type: GrantFiled: February 6, 2004Date of Patent: January 31, 2006Assignee: International Business Machines CorporationInventors: Wenjie Li, Pushkara R. Varanasi, Alyssandrea H. Hamad
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Patent number: 6989226Abstract: An object of the present invention is to provide a photosensitive resin composition which is excellent in the compatibility (dispersibility) of photosensitive resin composition components, developability with aqueous developer solution, water resistance, image reproducibility, print wear characteristics in printing with a water base ink and plate wiping-off resistance in removal of ink adhered to any printing plate. The present invention relates to a photosensitive resin composition comprising a hydrophilic copolymer (A) obtained by copolymerizing at least (1) 2 to 15 parts by mass of an unsaturated monomer having a carboxyl group, (2) 50 to 80 parts by mass of a conjugated diene-type monomer, (3) 3 to 20 parts by mass of an aromatic vinyl compound, and (4) 3 to 30 parts by mass of an alkyl (meth)acrylate.Type: GrantFiled: November 27, 2001Date of Patent: January 24, 2006Assignee: Asahi Kasei Chemicals CorporationInventors: Yoshifumi Araki, Hiromi Kobayashi
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Patent number: 6989224Abstract: The invention provides novel polymers and photoresist compositions that comprise the polymers as a resin component. Polymers of the invention contain two distinct groups which can undergo a deblocking reaction in the presence of photogenerated acid, wherein one of the deblocking moieties is an acetal group. The second photoacid-labile group is suitably an ester, particularly as provided by polymerization of an alkyl acrylate group, such as t-butylmethacrylate.Type: GrantFiled: October 9, 2002Date of Patent: January 24, 2006Assignee: Shipley Company, L.L.C.Inventors: Timothy G. Adams, Matthew A. King
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Patent number: 6982140Abstract: There is provided a positive type resist composition formed by dissolving (A) a resin component with a unit derived from a (meth)acrylate ester in the principal chain, for which the solubility in alkali increases under the action of acid, and (B) an acid generator component which generates acid on exposure, in an organic solvent component (C), wherein the resin component (A) is a copolymer comprising (a1) a unit derived from a (meth)acrylate ester comprising an acid dissociable, dissolution inhibiting group containing a polycyclic group, (a2) a unit derived from a (meth)acrylate ester comprising a lactone containing monocyclic group or polycyclic group, (a3) a unit derived from a (meth)acrylate ester comprising a hydroxyl group containing polycyclic group, and (a4) a unit derived from a (meth)acrylate ester comprising a polycyclic group which is different from the unit (a1), the unit (a2) and the unit (a3).Type: GrantFiled: November 29, 2002Date of Patent: January 3, 2006Assignee: Tokyo Ohka Kogyo., Ltd.Inventors: Hideo Hada, Satoshi Fujimura, Jun Iwashita
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Patent number: 6974658Abstract: Disclosed is a polymer compound for photoresist characterized in that the polymer compound is formed of a polymer compound having at least one skeleton represented by the following general formula (1), general formula (2A), general formula (2B) or general formula (2C):Type: GrantFiled: April 30, 2003Date of Patent: December 13, 2005Assignee: Kabushiki Kaisha ToshibaInventors: Naomi Shida, Toru Ushirogouchi, Takuya Naito
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Patent number: 6974655Abstract: A chemically amplified photo-resist includes a polymer containing acid-labile radicals attached to a polar group and also contains anchor groups that allow attachment of a consolidating agent. The polymer includes first repeating units containing siloxane groups. The photoresist on the one hand exhibits an enhanced transparency for short-wavelength radiation and on the other hand permits chemical consolidation of the structured resist. A process for producing structured resists is a also described.Type: GrantFiled: September 3, 2002Date of Patent: December 13, 2005Assignee: Infineon Technologies AGInventors: Jörg Rottstegge, Christoph Hohle, Christian Eschbaumer, Michael Sebald, Wolf-Dieter Domke
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Patent number: 6969579Abstract: Thermally imageable elements useful as lithographic printing plate precursors are disclosed. The elements may be either single layer or multilayer elements and comprise an alkali soluble co-polymer, or a mixture of alkali soluble co-polymers. The resulting printing plates have good resistance to pressroom chemicals.Type: GrantFiled: December 21, 2004Date of Patent: November 29, 2005Assignee: Eastman Kodak CompanyInventors: Anthony Paul Kitson, Kevin Barry Ray
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Patent number: 6969577Abstract: A positive resist composition comprising (A) a resin having a specific structure and capable of decomposing under action of an acid to increase solubility in an alkali developer, and (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation.Type: GrantFiled: March 4, 2004Date of Patent: November 29, 2005Assignee: Fuji Photo Film Co., Ltd.Inventor: Yutaka Adegawa
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Patent number: 6969570Abstract: Thermally imageable elements useful as lithographic printing plate precursors are disclosed. The elements comprise a substrate, an underlayer over the substrate, and a top layer over the underlayer. The top layer comprises a co-polymer that comprises, in polymerized form, norbornene or a norbornene derivative. The resulting lithographic printing plates have good resistance to pressroom chemicals.Type: GrantFiled: October 26, 2004Date of Patent: November 29, 2005Assignee: Kodak Polychrome Graphics, LLCInventor: Paul Kitson
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Patent number: 6964840Abstract: A radiation-sensitive resin composition comprising an acid-labile group-containing resin and a photoacid generator is disclosed. The resin has a structure of the formula (1), wherein R1 represents a hydrogen atom, a monovalent acid-labile group, an alkyl group having 1-6 carbon atoms which does not have an acid-labile group, or an alkylcarbonyl group having 2-7 carbon atoms which does not have an acid-labile group, X1 represents a linear or branched fluorinated alkyl group having 1-4 carbon atoms, and R2 represents a hydrogen atom, a linear or branched alkyl group having 1-10 carbon atoms, or a linear or branched fluorinated alkyl group having 1-10 carbon atoms. The resin composition exhibits high transmittance of radiation, high sensitivity, resolution, and pattern shape, and is useful as a chemically amplified resist in producing semiconductors at a high yield.Type: GrantFiled: June 16, 2004Date of Patent: November 15, 2005Assignees: JSR Corporation, International Business Machines CorporationInventors: Yukio Nishimura, Noboru Yamahara, Masafumi Yamamoto, Toru Kajita, Tsutomu Shimokawa, Hiroshi Ito
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Patent number: 6964839Abstract: A photosensitive copolymer has a weight-average molecular weight of 3,000 to 100,000 and is represented by the following formula: wherein R1 is a hydrogen atom or methyl, R2 is an acid-labile tertiary alkyl group, and m/(m+n) is 0.5 to 0.8.Type: GrantFiled: November 20, 2000Date of Patent: November 15, 2005Assignee: Samsung Electronics Co., Ltd.Inventors: Sang-jun Choi, Hyun-woo Kim, Sang-gyun Woo, Joo-tae Moon
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Patent number: 6962767Abstract: Acetal compounds in which a 5- or 6-membered ring acetal structure is connected to a norbornene structure through a linker represented by —(CH2)m— in which one hydrogen atom may be substituted with a hydroxyl or acetoxy group, and m is from 1 to 8 are novel. Using the acetal compounds as a monomer, polymers are obtained. A resist composition comprising the polymer as a base resin is sensitive to high-energy radiation and has excellent sensitivity, resolution, and etching resistance.Type: GrantFiled: December 10, 2002Date of Patent: November 8, 2005Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Takeshi Kinsho, Koji Hasegawa, Tsunehiro Nishi, Mutsuo Nakashima, Seiichiro Tachibana, Jun Hatakeyama
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Patent number: 6953651Abstract: A chemical amplifying type positive resist composition having excellent sensitivity and resolution, manifesting no generation of scum is provided, which comprises a resin which has a polymerization unit derived from hydroxystyrene and a polymerization unit derived from 2-ethyl-2-adamantyl (meth)acrylate, and is insoluble or poorly soluble itself in an alkali, but becomes alkali-soluble after dissociation of the above-mentioned acid unstable group by the action of an acid; a radiation sensitive acid generating agent; and polypropylene glycol.Type: GrantFiled: January 17, 2002Date of Patent: October 11, 2005Assignee: Sumitomo Chemical Company, LimitedInventors: Katsuhiko Namba, Junji Nakanishi, Yasunori Uetani
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Patent number: 6951706Abstract: The present invention provides a sulfonate of the formula (I): wherein Q1, Q2, Q3, Q4 and Q5 each independently represent hydrogen, alkyl having 1 to 16 carbon atoms, alkoxy having 1 to 16 carbon atoms, halogen, aryl having 6 to 12 carbon atoms, aralkyl having 7 to 12 carbon atoms, cyano, sulfide, hydroxy, nitro or a group of the formula (I?) —COO—X—Cy1??(I?) wherein X represents alkylene and at least one —CH2— in the alkylene may be substituted by —O— or —S—, and Cy1 represents alicyclic hydrocarbon having 3 to 20 carbon atoms, and A+ represents a counter ion, with the proviso that at least one of Q1, Q2, Q3, Q4 and Q5 is the group of the formula (I?).Type: GrantFiled: August 25, 2003Date of Patent: October 4, 2005Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Yasunori Uetani, Hiroshi Moriuma
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Patent number: 6951705Abstract: Nitrile/vinyl ether-containing polymers for photoresist compositions and microlithography methods employing the photoresist compositions are described. These photoresist compositions comprise 1) at least one ethylenically unsaturated compound comprised of a vinyl ether and 2) a nitrile-containing compound, e.g., acrylonitrile, which together impart high ultraviolet (UV) transparency and developability in basic media. In some embodiments, these photoresist compositions further comprise a fluoroalcohol group. The photoresist compositions of this invention have, high UV transparency, particularly at short wavelengths, e.g., 157 nm and 193 nm, which property makes them useful for lithography at these short wavelengths.Type: GrantFiled: May 4, 2001Date of Patent: October 4, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: Michael Fryd, Periyasamy Mookkan, Frank Leonard Schadt, III
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Patent number: 6949323Abstract: Resist compositions comprising as the base resin a polymer using tert-amyloxystyrene as a reactive group which is decomposable under the action of an acid to increase solubility in alkali have advantages including a significantly enhanced contrast of alkali dissolution rate before and after exposure, a high sensitivity, and a high resolution in the baking temperature range of 100-110° C. which is unachievable with tert-butoxystyrene. The compositions are best suited as a chemically amplified resist material for micropatterning in the manufacture of VLSI.Type: GrantFiled: October 30, 2002Date of Patent: September 27, 2005Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takanobu Takeda, Osamu Watanabe, Kazunori Maeda, Hiroshi Miyakoshi
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Patent number: 6946233Abstract: Provided are a resist material having markedly high resolution and etching resistance of a practically usable level, and being useful for fine microfabrication; a patterning method using the resist material; and a polymer useful as a base resin for the resist material. More specifically, provided are a polymer having a weight-average molecular weight of 1,000 to 500,000, which comprises one or more repeating units selected from the group consisting of repeating units represented by formulae (1) to (3) below; and one or more repeating units of the formula (4) below; and a resist material containing the polymer.Type: GrantFiled: July 22, 2002Date of Patent: September 20, 2005Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsunehiro Nishi, Takeshi Kinsho
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Patent number: 6946235Abstract: A resist composition comprising a polymer containing vinyl sulfonate units having fluorinated hydrophilic groups as a base resin has excellent transparency, substrate adhesion and developer penetrability as well as plasma etching resistance, and is suited for lithographic microprocessing.Type: GrantFiled: August 8, 2003Date of Patent: September 20, 2005Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Michitaka Ootani, Haruhiko Komoriya
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Patent number: 6936402Abstract: Disclosed herein is a novel norbornene, acrylate or methacrylate monomer as a photoresist monomer containing an oxepan-2-one group. Further disclosed are photoresist compositions comprising a polymer prepared from the monomer, methods for preparing the photoresist compositions, and methods for forming photoresist patterns using the photoresist compositions.Type: GrantFiled: February 24, 2004Date of Patent: August 30, 2005Assignee: Korea Advanced Institute Science & TechnologyInventors: Jin-Baek Kim, Tae-Hwan Oh, Jae-Hak Choi, Jae-Jun Lee
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Patent number: 6936400Abstract: A negative resist composition is provided which is less likely to swell in an alkali developing solution. An alkali-developable negative resist composition is disclosed comprising a compound (A) which generates an acid upon exposure to radiation, and a resin component (B) which becomes insoluble in alkali under the action of an acid, wherein the component (B) is a resin component containing: (b1) a unit which becomes insoluble in an alkali solution as a result of the formation of a lactone under the action of an acid generated from the component (A), and (b2) a unit having an alcoholic hydroxyl group.Type: GrantFiled: June 25, 2003Date of Patent: August 30, 2005Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Ryoichi Takasu, Miwa Miyairi, Jun Iwashita, Toshikazu Tachikawa
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Patent number: 6929897Abstract: Polymers and co-polymers having monomeric units formed by the polymerization of monomers of the Structure I where R1 is a moiety containing an ethylenically unsaturated polymerizable group, R2 is a C1-C3 alkylene group, and R3 is a C1-10 linear or cyclic alkyl group, a C6-10 aromatic or substituted aromatic group, a C1-8 alkoxy methyl, or a C1-8 alkoxy ethyl group, are useful as binder resins for photosensitive compositions, and processes for photolithography in the production of semiconductor devices and materials.Type: GrantFiled: August 19, 2004Date of Patent: August 16, 2005Assignee: Arch Specialty Chemicals, Inc.Inventors: Patrick Foster, Gregory Spaziano, Binod B De
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Patent number: 6929896Abstract: A chemically amplified photoresist composition comprising, (a) a compound which cures upon the action of an acid or a compound whose solubility is increased upon the action of an acid; and (b) as photosensitive acid donor, at least one compound of the formula Ia, Ib, Ic, IIb or IIc wherein R1 is for example C1-C5alkyl, C3-C30cycloalkyl, C1-C5haloalkyl, C2-C12alkenyl, C4-C8cycloalkenyl, C6-C12bicycloalkenyl, phenyl, naphthyl, anthracyl, phenanthryl, or is a heteroaryl radical; all of which are unsubstituted or substituted; optionally some of the substituents form 5- or 6-membered rings with further substituents on the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring or with one of the carbon atoms of the phenyl, naphtyl, anthracyl, phenanthryl, or heteroaryl ring; R?1 is for example C1-C12alkylene, C3-C30cycloalkylene, phenylene, naphtylene, diphenylene, or oxydiphenylene, wherein these radicals are unsubstituted or substituted; A and B for example are a direct bond; Ar1 and Ar2 independently of eaType: GrantFiled: November 26, 2001Date of Patent: August 16, 2005Assignee: Ciba Specialty Chemicals CorporationInventors: Hitoshi Yamato, Toshikag Asakura, Akira Matsumoto, Masaki Ohwa
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Patent number: 6927011Abstract: A resist resin containing a monomer unit selected from the group comprising a monomer unit represented by Formula (II): wherein a substituent R3 represents an alkyl group, or a functional group comprising an acid-deprotectable protecting group, m representing the number of R3 is 0 (non-substitution), 1, 2 or more, R3 may be different from each other, provided that m is 2 or more, and n represents an integer of 0 to 4, has no rough spots on the surface after etching and so has good dry etching resistance, and therefore the resist resin is preferably used as a photo resist for DUV.Type: GrantFiled: February 9, 2001Date of Patent: August 9, 2005Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Tadayuki Fujiwara, Yukiya Wakisaka, Toru Tokimitsu, Naoshi Murata, Yoshihiro Kamon, Hikaru Momose
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Patent number: 6927009Abstract: A positive photosensitive composition comprising (A) a specific acid generator that generates an acid upon irradiation of an actinic ray or radiation, and (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase solubility in an alkali developing solution.Type: GrantFiled: May 21, 2002Date of Patent: August 9, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Kunihiko Kodama, Kenichiro Sato, Toru Fujimori
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Patent number: 6924079Abstract: The present invention relates to a resist resin having an acid-decomposable group, which gives rise to decomposition of the acid-decomposable group to show an increased solubility to an aqueous alkali solution by the action of an acid, wherein the resist resin has, in the main chain, an alicyclic lactone structure represented by the following general formula (1). According to the present invention, a positive-type chemically amplified resist can be obtained which has high transparency to a far-ultraviolet light having a wavelength of about 220 nm or less, excellent etching resistance, and excellent adhesion to substrate; and a fine pattern required in production of semiconductor device can be formed. (wherein Z is an alicyclic hydrocarbon group having a lactone structure).Type: GrantFiled: July 2, 2001Date of Patent: August 2, 2005Assignee: NEC CorporationInventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
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Patent number: 6916591Abstract: 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: GrantFiled: March 21, 2003Date of Patent: July 12, 2005Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Katsuhiro Kobayashi, Katsuya Takemura, Junji Tsuchiya, Kazunori Maeda
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Patent number: 6916598Abstract: This invention discloses compositions that can be polymerized/crosslinked imagewise upon exposure to ionization radiation such as x-ray, electron beam, ion beam, and gamma-ray. This invention also discloses methods of use for these compositions for microfabrication of ceramics, for stereolithography, and for x-ray, e-beam, and ion-beam lithography which can be used for photoresists.Type: GrantFiled: March 21, 2003Date of Patent: July 12, 2005Assignee: E. I. du Pont de Nemours and CompanyInventor: Ying Wang
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Patent number: 6916592Abstract: A resist composition comprising a base polymer having a fluorinated sulfonate or fluorinated sulfone introduced therein is sensitive to high-energy radiation, has excellent transparency, contrast and adherence, and is suited for lithographic microprocessing.Type: GrantFiled: March 25, 2003Date of Patent: July 12, 2005Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Michitaka Ootani, Haruhiko Komoriya
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Patent number: 6911296Abstract: The present invention also includes an imageable element, comprising a substrate and a thermally imageable composition comprising a thermally sensitive polymer which exhibits an increased solubility in an aqueous developer solution upon heating. The thermally sensitive polymer includes at least one covalently bonded unit and at least one thermally reversible non-covalently bonded unit, which includes a two or more centered H-bond within each of the non-covalently bonded unit. The present invention also includes a method of producing the imaged element. The present invention still further includes a thermally imageable composition comprising comprising a thermally sensitive polymer according to the present invention and a process for preparing the thermally sensitive polymer, which is a supramolecular polymer.Type: GrantFiled: November 19, 2002Date of Patent: June 28, 2005Assignee: Kodak Polychrome Graphics LLCInventors: Peter S. Pappas, Alan Monk, Shashikant Saraiya, Jianbing Huang
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Patent number: 6911293Abstract: Disclosed is a photoresist composition comprising: a) at least one film forming resin selected from the group consisting of novolak resins, and polyhydroxystyrenes; b) at least one photoactive compound or photoacid generator; and c) a solvent composition comprising at least one solvent selected from the group consisting of acetals and ketals. Also disclosed is a photoresist composition comprising a polycarbonate resin and a solvent composition comprising at least one solvent selected from the group consisting of acetals and ketals. Also disclosed is a process for imaging a photoresist composition, comprising the steps of: a) coating a suitable substrate with any of the aforementioned photoresist compositions; b) baking the substrate to substantially remove the solvent; c) imagewise irradiating the photoresist film; and d) removing the imagewise exposed or, alternatively, the unexposed areas of the coated substrate with a suitable developer.Type: GrantFiled: April 11, 2002Date of Patent: June 28, 2005Assignee: Clariant Finance (BVI) LimitedInventors: Stanley F. Wanat, Joseph E. Oberlander, Robert R. Plass, Douglas McKenzie
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Patent number: 6897012Abstract: Disclosed is a chemical-amplification negative-working photoresist composition used for photolithographic patterning in the manufacture of semiconductor devices suitable for patterning light-exposure to ArF excimer laser beams and capable of giving a high-resolution patterned resist layer free from swelling and having an orthogonal cross sectional profile by alkali-development. The characteristic ingredient of the composition is the resinous compound which has two types of functional groups, e.g., hydroxyalkyl groups and carboxyl or carboxylate ester groups, capable of reacting each with the other to form intramolecular and/or intermolecular ester linkages in the presence of an acid released from the radiation-sensitive acid generating agent to cause insolubilization of the resinous ingredient in an aqueous alkaline developer solution.Type: GrantFiled: May 4, 2004Date of Patent: May 24, 2005Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Takeshi Iwai, Satoshi Fujimura
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Patent number: 6893794Abstract: A chemical amplification type positive resist composition comprising: (A) a resin which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, and which contains a structural unit derived from p-hydroxystyrene and a structural unit represented by the formula (Ia) or (Ib) wherein R1 and R2 each independently represents hydrogen or methyl, and R3 to R5 each independently represents alkyl having 1 to 8 carbon atoms; and (B) radiation-sensitive acid generator comprising sulfonic acid ester of N-hydroxyimide compound; and onium salt is provided.Type: GrantFiled: July 21, 2003Date of Patent: May 17, 2005Assignee: Sumitomo Chemical Company, LimitedInventors: Makoto Akita, Satoshi Yamaguchi
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Patent number: 6890697Abstract: Disclosed is a novel positive-working chemical-amplification photoresist composition capable of giving an extremely finely patterned resist layer in the manufacturing process of semiconductor devices. The photoresist composition comprises: (A) 100 parts by weight of a copolymeric resin consisting of from 50 to 85% by moles of (a) hydroxyl group-containing styrene units, from 15 to 35% by moles of (b) styrene units and from 2 to 20% by moles of (c) acrylate or methacrylate ester units each having a solubility-reducing group capable of being eliminated in the presence of an acid; and (B) from 1 to 20 parts by weight of a radiation-sensitive acid-generating agent which is an onium salt containing a fluoroalkyl sulfonate ion having 3 to 10 carbon atoms as the anion such as bis(4-tert-butylphenyl) iodonium nonafluorobutane sulfonate.Type: GrantFiled: January 31, 2002Date of Patent: May 10, 2005Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Katsumi Oomori, Hiroto Yukawa, Ryusuke Uchida, Kazufumi Sato
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Patent number: 6887644Abstract: A resist composition includes a polymer principal chain, a carboxyl group having a protective group and bonding to a side chain of the polymer main chain, and an additional acidic functional group having an acid-cleavable protective group and bonding to a side chain of the polymer main chain, wherein the carboxyl group has a lactone structure represented by a formula (wherein n is an integer of 1-4, and R represents any of a hydrogen atom, an alkyl group, an alkoxyl group and an alkoxycarbonyl group and connected to an arbitrary position of said lactone structure excluding a second position forming an ester bonding) as the protective group.Type: GrantFiled: January 29, 1998Date of Patent: May 3, 2005Assignee: Fujitsu LimitedInventors: Koji Nozaki, Ei Yano
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Patent number: 6887646Abstract: The present invention discloses a chemically amplified resist composition comprising: a resin which becomes soluble in an aqueous alkali solution in the presence of an acid, a photo acid generator, and an amine derivative which shows, in water of 25° C., such a basicity as to form a conjugate acid and has a medium polarity. The amine derivative acts as a quencher. Therefore, the chemically amplified resist composition of the present invention enables formation of a very precise and fine resist pattern and can be suitably used particularly in a lithography using an ArF excimer laser beam.Type: GrantFiled: July 11, 2000Date of Patent: May 3, 2005Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Tadayuki Fujiwara, Yukiya Wakisaka, Masayuki Tooyama
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Patent number: 6884566Abstract: A novel copolymer includes a repeating unit (B) derived from an unsaturated carboxylic anhydride, a repeating unit (C) represented by Formula (II), and a repeating unit (D) represented by Formula (III).Type: GrantFiled: October 16, 2003Date of Patent: April 26, 2005Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Tsuyoshi Nakamura, Taeko Ikegawa, Atsushi Sawano, Kousuke Doi, Hidekatsu Kohara
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Patent number: 6884564Abstract: Fluorinated polymers, photoresists and associated processes for microlithography are described. These polymers and photoresists are comprised of esters derived from fluoroalcohol functional groups that simultaneously impart high ultraviolet (UV) transparency and developability in basic media to these materials. The materials of this invention have high UV transparency, particularly at short wavelengths, e.g., 157 nm, which makes them highly useful for lithography at these short wavelengths.Type: GrantFiled: October 25, 2002Date of Patent: April 26, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Jerald Feldman, Frank L. Schadt, III, Gary Newton Taylor
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Patent number: 6884562Abstract: Positive photoresists and associated processes for microlithography in the ultraviolet (UV) and violet are disclosed. The photoresists comprise (a) a branched copolymer containing protected acid groups and (b) at least one photoacid generator. The photoresists have high transparency throughout the UV, good development properties, high plasma etch resistance and other desirable properties, and are useful for microlithography in the near, far, and extreme UV, particularly at wavelengths less than or equal to 365 nm.Type: GrantFiled: October 26, 1999Date of Patent: April 26, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: Frank Leonard Schadt, III, Michael Fryd, Mookkan Periyasamy
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Patent number: 6878504Abstract: A chemically-amplified resist composition is disclosed, which comprises a polymer of formula (I) below: wherein R1 is H, C1-C4 alkyl, or CF3; Q is C4-C12 cycloalkyl; R2 is H, C1-C4 alkyl, or CF3; R3 is C4-C12 branched or cyclic alkyl; and x+y+z equals to 1. The chemically-amplified resist compositions of the present invention not only can be applied maturely to general lithographic processes, especially to 193 nm lithographic process, but also have excellent photo-sensitivity, and can form a well-resolved pattern and profile.Type: GrantFiled: May 28, 2003Date of Patent: April 12, 2005Assignee: Everlight USA, Inc.Inventors: Chi-Sheng Chen, Chan-Chan Tsai, Bin Jian, Hsin-Ming Liao
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Patent number: 6875552Abstract: The present invention provides a photoresist composition that reduces standing wave and side wall roughness. The composition comprises a first photoresist X and a second photoresist Y. The first photoresist X absorbs at a higher wavelength than the second photoresist Y. The second photoresist Y has a lower glass transitional temperature than the first photoresist X. A method for making the photoresist composition is also provided.Type: GrantFiled: August 9, 2002Date of Patent: April 5, 2005Assignee: Micron Technology, Inc.Inventor: Yoshiki Hishiro
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Patent number: 6875556Abstract: A resist composition comprising as the base resin a blend of a fluorinated polymer which is sensitive to high-energy radiation and highly transparent at a wavelength of up to 200 nm and a sulfonate-containing polymer exhibiting a high contrast upon alkali dissolution is improved in transparency and alkali dissolution contrast as well as plasma etching resistance.Type: GrantFiled: October 23, 2003Date of Patent: April 5, 2005Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Haruhiko Komoriya, Satoru Miyazawa
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Patent number: 6872514Abstract: A resist composition comprising a base polymer having a fluorinated sulfonate or fluorinated sulfone introduced therein is sensitive to high-energy radiation below 300 nm, has excellent transparency, contrast and adherence, and is suited for lithographic microprocessing.Type: GrantFiled: March 25, 2003Date of Patent: March 29, 2005Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Michitaka Ootani, Haruhiko Komoriya
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Patent number: 6872505Abstract: By using a branched long chained chain scission polymer as a photoresist for EUV and 157 nanometer applications, a relatively higher molecular weight polymer with good mechanical properties may be achieved. In addition, by using chain scission technology, line edge roughness and resolution may be improved at the same time.Type: GrantFiled: September 16, 2003Date of Patent: March 29, 2005Assignee: Intel CorporationInventors: Heidi B. Cao, Robert P. Meagley
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Patent number: 6869744Abstract: A chemically amplified positive resist composition contains as a base a carboxyl or phenolic hydroxyl group-containing resin soluble in aqueous alkaline solution, in which acid labile groups are incorporated into at least some of the hydrogen atoms on the carboxyl or phenolic hydroxyl groups so that the resin becomes insoluble or substantially insoluble in alkali, wherein the resin contains acid labile groups of at least two types, acid labile groups of one type are acetal or ketal groups, and acid labile groups of the other type are tertiary hydrocarbon groups or tertiary hydrocarbon group-containing substituents. The resist composition remains stable during vacuum standing after exposure to electron beams or soft x-rays, leaves minimal footings on chromium substrates, has an excellent sensitivity and resolution, and is thus suited as a micropatterning material for use in the processing of mask substrates.Type: GrantFiled: July 19, 2001Date of Patent: March 22, 2005Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Jun Hatakeyama
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Patent number: 6869745Abstract: Disclosed is a novel positive-working chemical-amplification photoresist composition capable of giving an extremely finely patterned resist layer in the manufacturing process of semiconductor devices. The photoresist composition comprises: (A) 100 parts by weight of a copolymeric resin consisting of from 50 to 85% by moles of (a) hydroxyl group-containing styrene units, from 15 to 35% by moles of (b) styrene units and from 2 to 20% by moles of (c) acrylate or methacrylate ester units each having a solubility-reducing group capable of being eliminated in the presence of an acid; and (B) from 1 to 20 parts by weight of a radiation-sensitive acid-generating agent which is an onium salt containing a fluoroalkyl sulfonate ion having 3 to 10 carbon atoms as the anion such as bis(4-tert-butylphenyl) iodonium nonafluorobutane sulfonate.Type: GrantFiled: January 31, 2002Date of Patent: March 22, 2005Assignee: Tokyo Ohka Kogyo, Co., Inc.Inventors: Katsumi Oomori, Hiroto Yukawa, Ryusuke Uchida, Kazufumi Sato
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Patent number: 6866981Abstract: There are disclosed a light-sensitive composition which comprises (A) at least one water-soluble polymer selected from a cationic water-soluble polymer having a phenyl group substituted by a vinyl group at a side chain of the polymer and a water-soluble polymer having a phenyl group substituted by a vinyl group and a sulfonate group at a side chain of the polymer, and (B) at least one of a photopolymerization initiator and a photo-acid generator; and a light-sensitive composition which comprises at least one cationic monomer having two or more polymerizable unsaturated groups in the molecule, at least one polymer, and at least one of a photopolymerizable initiator and a photo-acid generator.Type: GrantFiled: October 30, 2002Date of Patent: March 15, 2005Assignee: Mitsubishi Paper Mills LimitedInventors: Akira Furukawa, Kunihiro Doi
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Patent number: 6864037Abstract: A copolymer of an acrylic monomer having at least one C6-20 alicyclic structure with a norbornene derivative or styrene monomer having a hexafluoroalcohol pendant is highly transparent to VUV radiation and resistant to plasma etching. A resist composition using the polymer as a base resin is sensitive to high-energy radiation below 200 nm, has excellent sensitivity, transparency and dry etching resistance, and is suited for lithographic microprocessing.Type: GrantFiled: June 25, 2002Date of Patent: March 8, 2005Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co. Ltd., Central Glass Co., Ltd.Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Michitaka Ootani, Satoru Miyazawa, Kentaro Tsutsumi, Kazuhiko Maeda