Sulfur In Heterocyclic Ring Patents (Class 430/922)
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Patent number: 7560219Abstract: Sulfonium salt photoinitiator compositions, precursors useful in the preparation of such photoinitiators and the use of these photoinitiators in, e.g., UV curable adhesives, UV curable sealants, UV curable coating compositions, such as printing inks and varnishes, and UV curable encapsulants.Type: GrantFiled: April 26, 2007Date of Patent: July 14, 2009Assignee: Henkel AG & Co. KGaAInventors: Yuxia Liu, Donald E. Herr
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Patent number: 7550253Abstract: A resist film made of a chemically amplified resist is formed on a substrate. Subsequently, a barrier film for preventing a component of the resist film from eluting into an immersion liquid or preventing the immersion liquid from permeating into the resist film is formed on the resist film. Thereafter, with an immersion liquid provided on the barrier film, pattern exposure is carried out by selectively irradiating the resist film with exposing light through the barrier film. Then, after removing the barrier film, the resist film having been subjected to the pattern exposure is developed, so as to form a resist pattern made of the resist film.Type: GrantFiled: February 16, 2005Date of Patent: June 23, 2009Assignee: Panasonic CorporationInventors: Masayuki Endo, Masaru Sasago
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Patent number: 7541131Abstract: The invention provides a resist composition for use in the production process of a semiconductor such as IC, in the production of a circuit substrate of liquid crystal, thermal head and the like or in other photofabrication processes, a compound for use in the resist composition and a pattern forming method using the resist composition, which are a resist composition comprising (A) a sulfonium salt represented by the following formula (I); and a pattern forming method using the resist composition: wherein R1 represents an alkyl group or an aryl group, R2 to R9 each independently represents a hydrogen atom or a substituent and may combine with each other to form a ring, Z represents an electron-withdrawing divalent linking group, Xn? represents an n-valent anion, n represents an integer of 1 to 3, and m represents the number of anions necessary for neutralizing the electric charge.Type: GrantFiled: February 17, 2006Date of Patent: June 2, 2009Assignee: FUJIFILM CorporationInventor: Yasutomo Kawanishi
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Patent number: 7531286Abstract: 1. A radiation-sensitive resin composition comprising: (A) a resin insoluble or scarcely soluble in alkali, but becomes alkali soluble by the action of an acid and (B) a photoacid generator. The resin comprises (a) at least one recurring unit of the following formula (1-1) or (1-2), and (b) at least one recurring unit for the following formula (2-1), (2-2), or (2-3).Type: GrantFiled: March 13, 2003Date of Patent: May 12, 2009Assignee: JSR CorporationInventors: Yukio Nishimura, Hiroyuki Ishii, Masafumi Yamamoto, Isao Nishimura
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Patent number: 7527913Abstract: A photoresist composition includes about 4% to about 10% by weight of a photoresist resin, about 0.1% to about 0.5% by weight of a photoacid generator having a sulfonium-salt cationic group and a sulfonium-salt anionic group containing a carboxyl group as a hydrophilic site and a remainder of a solvent. The photoresist composition may form a photoresist pattern having a uniform profile.Type: GrantFiled: January 24, 2008Date of Patent: May 5, 2009Assignee: Samsung Electronics Co., Ltd.Inventors: Hyo-Jin Yun, Young-Gil Kwon, Young-Ho Kim, Do-Young Kim, Jae-Hee Choi, Se-Kyung Baek
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Patent number: 7524611Abstract: Image formation via photoinduced fluorescence changes in a polymeric medium with two-photon fluorescence readout of a multi-layer structure. Fluorophore-containing polymers, possessing one or more basic functional groups, underwent protonation in the presence of a photoinduced acid generator upon exposure to a broad-band UV light source or fast-pulsed red to near-IR laser irradiation. Solution studies demonstrated formation of monoprotonated and diprotonated species upon irradiation, each resulting in distinctly different absorption and fluorescence properties. The fluorescence of the original, neutral, fluorophore was reduced upon monoprotonation, leading to a concomitant increase in fluorescence at longer wavelengths due to the monoprotonated form, the basis for multichannel data readout.Type: GrantFiled: September 26, 2007Date of Patent: April 28, 2009Assignee: University of Central Florida Research Foundation, Inc.Inventor: Kevin D. Belfield
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Patent number: 7521168Abstract: 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: GrantFiled: February 11, 2003Date of Patent: April 21, 2009Assignee: Fujifilm CorporationInventors: Kazuyoshi Mizutani, Hyou Takahashi
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Patent number: 7510822Abstract: A stimulation sensitive composition comprising: (A) a compound represented by the specific formula which is capable of generating an acid or a radical by stimulation from the external.Type: GrantFiled: April 9, 2003Date of Patent: March 31, 2009Assignee: FUJIFILM CorporationInventor: Kunihiko Kodama
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Patent number: 7498126Abstract: A photoacid generator has formula (1). A chemically amplified resist composition comprising the photoacid generator has advantages including a high resolution, focus latitude, long-term PED dimensional stability, and a satisfactory pattern profile shape. When the photoacid generator is combined with a resin having acid labile groups other than those of the acetal type, resolution and top loss are improved. The composition is suited for deep UV lithography.Type: GrantFiled: June 5, 2007Date of Patent: March 3, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Kazunori Maeda, Satoshi Watanabe
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Patent number: 7491485Abstract: This resist composition according to the present invention includes a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid, and an acid generator component (B) which generates an acid upon exposure, wherein the acid generator component (B) includes an acid generator (B1) represented by a general formula (b1-6-1) shown below and an acid generator (B2) represented by a general formula (b1-6-2) shown below: (wherein, R40 represents a hydrogen atom or an alkyl group; R41 represents a halogen atom, a halogenated alkyl group, an alkyl group, an acetyl group, a carboxyl group or a hydroxyalkyl group; R42 and R43 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an acetyl group, an alkoxy group, a carboxyl group or a hydroxyalkyl group; n0 to n3 each independently represents an integer of 0 to 3, with the proviso that n0+n1 is 5 or less; R13 each independently represents a linear or branched alkyl group of 1 to 10 carbonType: GrantFiled: May 20, 2008Date of Patent: February 17, 2009Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Masaru Takeshita, Komei Hirahara
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Patent number: 7491484Abstract: In a photoresist composition and a method of forming a pattern using the same, the photoresist composition includes about 0.1 to about 0.5 percent by weight of a photoacid generator including a positively charged sulfonium ion and a negatively charged sulfonate ion having a hydrophilic carboxylic group, about 4 to about 10 percent by weight of a resin, and a solvent.Type: GrantFiled: October 10, 2007Date of Patent: February 17, 2009Assignee: Samsung Electronics Co., Ltd.Inventors: Hyo-Jin Yun, Young-Gil Kwon, Do-Young Kim, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim
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Patent number: 7488568Abstract: A resist composition including a base component (A) and an acid-generator component (B), the acid-generator component (B) including an acid generator (B1) including a compound represented by general formula (b1-8) shown below (wherein R401 represents an acid dissociable, dissolution inhibiting group; R41 to R43 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an acetyl group, an alkoxy group, a carboxy group or a hydroxyalkyl group; Q represents a divalent linking group or a single bond; and X? represents an anion) or an acid generator (B1?) including a compound represented by general formula (b1-9) shown below (wherein R402 and R403 each independently represents a hydrogen atom, an alkyl group or a halogenated alkyl group; R404 represents an alkyl group or a halogenated alkyl group, wherein R403 and R404 may be bonded to each other to form a ring structure; and X? represents an anion).Type: GrantFiled: April 1, 2008Date of Patent: February 10, 2009Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takeshi Iwai, Hideo Hada, Masaru Takeshita, Akiya Kawaue, Keita Ishiduka, Hiroaki Shimizu, Kyoko Ohshita, Tsuyoshi Nakamura, Komei Hirahara, Yuichi Suzuki, Takehiro Seshimo, Kensuke Matsuzawa
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Patent number: 7465528Abstract: A positive-working photosensitive composition that includes (A) a resin containing repeating units having diamantane structures and capable of decomposing under action of an acid to increase solubility in an alkali developer, (B) a compound capable of generating a specific organic acid upon irradiation with an actinic ray or radiation, and (C) a solvent.Type: GrantFiled: October 17, 2006Date of Patent: December 16, 2008Assignee: FUJIFILM CorporationInventors: Fumiyuki Nishiyama, Kunihiko Kodama
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Patent number: 7396899Abstract: The present invention provides a sulfonium salt of the formula (Ia) a polymeric compound comprising a structural unit of the formula (Ib) and a chemical amplification type positive resist composition comprising (A) an acid generator comprising at least one compound selected from the group consisting of a sulfonium salt of the formula (Ia), a polymeric compound comprising a structural unit of the formula (Ib), and a sulfonium salt of the formula (Ic); and (B) resin which contains a structural unit having an acid labile group and 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.Type: GrantFiled: December 22, 2006Date of Patent: July 8, 2008Assignee: Sumitomo Chemical Co., Ltd.Inventors: Airi Yamada, Yasunori Uetani, Akira Kamabuchi
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Patent number: 7390613Abstract: The present application relates to a compound of formula Ai Xi Bi where Ai and Bi are each individually an organic onium cation; and Xi is anion of the formula ?O3S—CF2CF2OCF2CF2—SO3?. The compounds are useful as photoactive materials.Type: GrantFiled: December 4, 2006Date of Patent: June 24, 2008Assignee: AZ Electronic Materials USA Corp.Inventors: M. Dalil Rahman, David L. Rentkiewicz
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Patent number: 7387865Abstract: A composition containing a photoacid generator monomer and surfactant, and a method for synthesizing a compound on a substrate using the composition are provided. The method includes bonding a layer of first molecules having an acid labile protecting group to a solid substrate; coating a layer of the photoacid generator monomer composition according to the present invention on the layer of first molecules; exposing the composition layer to light and then heat-treating to remove the acid labile protecting group from the first molecules corresponding to the exposed portion; washing and removing the composition layer from the exposed and unexposed portions; and bonding second molecules to the exposed first molecules.Type: GrantFiled: July 20, 2004Date of Patent: June 17, 2008Assignee: Samsung Electronics Co., Ltd.Inventors: Sung-ouk Jung, Seung-ju Seo, Jae-chan Park
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Patent number: 7378223Abstract: The invention provides photoresist resin compositions and in particular, a photoresist resin compositions comprising a) an acrylate monomer having two urethane bonds, b) a crosslinkable urethane monomer having at least two ethylene double bonds, c) an alkali-soluble compound, d) a photopolymerization initiator and e) a solvent, and a photoresist dry film resists using the photoresist resins. The photoresist resin compositions and the photoresist dry film resists using the same in accordance with the invention have excellent adhesion to a substrate and sandblast resistance and at the same time, they have high sensitivity as well as high resolution, thereby enabling fine pattern formation on substrates.Type: GrantFiled: May 6, 2005Date of Patent: May 27, 2008Assignee: Dongjin Semichem, Co., Ltd.Inventors: Bong-gi Kim, Sung-mun Ryu, Seong-mo Park, Chan-seok Park
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Patent number: 7371503Abstract: A sulfonium salt compound excelling in transparency to deep ultraviolet rays at a wavelength of 220 nm or less, exhibiting well-balanced excellent performance such as sensitivity, resolution, pattern form, LER, and storage stability when used as a photoacid generator, a photoacid generator comprising the sulfonium salt compound, and a positive-tone radiation-sensitive resin composition containing the photoacid generator. The sulfonium salt compound is shown by the following formula (I), wherein R1 represents a halogen atom, an alkyl group, a monovalent alicyclic hydrocarbon group, an alkoxyl group, or —OR3 group, wherein R3 is a monovalent alicyclic hydrocarbon group, R2 represents a (substituted)-alkyl group or two or more R2 groups form a cyclic structure, p is 0-7, q is 0-6, n is 0-3, and X? indicates a sulfonic acid anion. The positive-tone radiation-sensitive resin composition comprises (A) a photoacid generator of the sulfonium-salt compound and (B) an acid-dissociable group-containing resin.Type: GrantFiled: January 9, 2004Date of Patent: May 13, 2008Assignee: JSR CorporationInventors: Takashi Miyamatsu, Hirokazu Niwata, Satoshi Ebata, Yong Wang
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Patent number: 7288363Abstract: A chemically amplified positive resist composition comprising a specific 2,4,6-triisopropylbenzenesulfonate compound as a photoacid generator, a polymer which changes its solubility in an alkaline developer under the action of acid, and a basic compound has a high sensitivity, a high contrast of dissolution of resist film, a high resolution, and good storage stability.Type: GrantFiled: April 14, 2005Date of Patent: October 30, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Ryuji Koitabashi, Satoshi Watanabe, Youichi Ohsawa
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Patent number: 7223518Abstract: Compositions and methods of use thereof are disclosed. One exemplary composition, among others, includes a polymer resin and a photoacid generator. In particular, the composition includes a polymer resin, wherein the polymer resin does not substantially absorb about 1 to 450 nanometer (nm) wavelength energy; and a photoacid generator, wherein the photoacid generator does substantially absorb about 1 to 450 nanometer (nm) wavelength energy.Type: GrantFiled: June 7, 2004Date of Patent: May 29, 2007Assignee: Georgia Tech Research CorporationInventors: Clifford L. Henderson, Trevor Hoskins, Cody M. Berger
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Patent number: 7214465Abstract: A positive photosensitive composition comprising (A1) a compound that generates an aromatic sulfonic acid substituted with at least one fluorine atom and/or a group having at least one fluorine atom upon irradiation of an actinic ray or radiation, (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, and (C) a compound that has at least three hydroxy or substituted hydroxy groups and at least one cyclic structure or (A2) an onium salt of an alkanesulfonic acid in which the ?-position of the sulfonic acid is not substituted with a fluorine atom and/or an onium salt of a carboxylic acid.Type: GrantFiled: January 9, 2003Date of Patent: May 8, 2007Assignee: Fujifilm CorporationInventors: Hajime Nakao, Yasumasa Kawabe, Toru Fujimori, Kunihiko Kodama
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Patent number: 7160667Abstract: The present invention relates to an image forming material having, on a substrate, an image forming layer that includes at least (A) a novolac type phenolic resin containing phenol as a structural unit, (B) a photo-thermal converting agent, and (C) a specific ammonium compound or a specific onium salt.Type: GrantFiled: January 21, 2004Date of Patent: January 9, 2007Assignee: Fuji Photo Film Co., Ltd.Inventor: Kaoru Iwato
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Patent number: 7160669Abstract: The present invention provides a sulfonium salt of the formula (Ia) a polymeric compound comprising a structural unit of the formula (Ib) and a chemical amplification type positive resist composition comprising (A) an acid generator comprising at least one compound selected from the group consisting of a sulfonium salt of the formula (Ia), a polymeric compound comprising a structural unit of the formula (Ib), and a sulfonium salt of the formula (Ic); and (B) resin which contains a structural unit having an acid labile group and 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.Type: GrantFiled: October 10, 2003Date of Patent: January 9, 2007Assignee: Sumitomo Chemical Company, LimitedInventors: Airi Yamada, Yasunori Uetani, Akira Kamabuchi
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Patent number: 7122294Abstract: Photoacid generators (PAGs) comprising photoactive moieties and perfluorinated, multifunctional anionic moieties (or incipient anionic moieties) are disclosed which provide photoacids with high acid strength, low volatility and low diffusivity. The present invention further relates to photoacid generators as they are used in photoinitiated or acid-catalyzed processes for uses such as photoresists for microlithography and photopolymerization.Type: GrantFiled: May 22, 2003Date of Patent: October 17, 2006Assignee: 3M Innovative Properties CompanyInventor: William M. Lamanna
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Patent number: 7094515Abstract: A stimulus sensitive composition containing a compound capable of generating an acid or a radical on receipt of an external stimulus, the compound being represented by the following formula (I): wherein Y represents a group having a bridged cyclic structure; R1 and R2 each independently represent a hydrogen atom, an alkyl group or an aryl group; R1 and R2 may be taken together to form a ring; Y1 and Y2 each independently represent an alkyl group or an aryl group; Y1 and Y2 may be taken together to form a ring; and X? represents a non-nucleophilic anion.Type: GrantFiled: March 15, 2004Date of Patent: August 22, 2006Assignee: Fuji Photo Film Co., Ltd.Inventors: Kunihiko Kodama, Hyou Takahashi
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Patent number: 7081326Abstract: 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; a multihydroxy-containing additive; and a resist polymer comprising a first repeating unit from a first monomer. The resist polymer may also comprise a second repeating unit from a second monomer, wherein the second monomer has an aqueous base soluble moiety. The multihydroxy-containing additive has the structure Q-(OH)m, where Q may include at least one alicycic group and m may be any integer between 2 and 6. 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 product that is insoluble in a developer solution.Type: GrantFiled: March 11, 2004Date of Patent: July 25, 2006Assignee: International Business Machines CorporationInventors: Wenjie Li, Pushkara R. Varanasi
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Patent number: 7078148Abstract: A radiation-sensitive resin composition comprising: (A) a resin comprising a hydroxyl group or carboxyl group, of which the hydrogen atom has been replaced by an acid-dissociable group possessing an alkali dissolution controlling capability, the resin increasing the solubility in an alkaline aqueous solution when the acid-dissociable group dissociates, and a photoacid generator comprising (B-1) a sulfonium salt represented by 1-(3,5-dimethyl-4-hydroxyphenyl)tetrahydrothiophenium perfluoro-n-octanesulfonate and 1-(4-n-butoxy-1-naphthyl)tetrahydrothiophenium nonafluoro-n-butanesulfonate and (B-2) a sulfonium salt represented by triphenylsulfonium nonafluoro-n-butanesulfonate. The radiation-sensitive resin composition useful as a novel chemically amplified resist exhibiting excellent sensitivity and resolution to deep ultraviolet rays typified by an ArF excimer laser, superior pattern shape-forming capability, and the like.Type: GrantFiled: May 29, 2003Date of Patent: July 18, 2006Assignee: JSR CorporationInventors: Motoyuki Shima, Hiroyuki Ishii, Atsushi Nakamura, Masafumi Yamamoto
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Patent number: 7033727Abstract: A photosensitive composition of the present invention has excellent sensitivity and pattern profile, which comprises an acid generator having a specific structure.Type: GrantFiled: September 24, 2003Date of Patent: April 25, 2006Assignee: Fuji Photo Film Co., Ltd.Inventor: Kunihiko Kodama
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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: 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: 6878505Abstract: A photosensitive composition comprising (i) a sensitizing dye represented by the following formula (I), (II) or (III) defined in the specification, (ii) a titanocene compound and (iii) a compound of undergoing a reaction with at least one of a radical and an acid to change at least one of its physical and chemical properties and maintaining the changed physical or chemical property, and a lithographic printing plate having a photosensitive layer comprising the photosensitive composition.Type: GrantFiled: May 28, 2002Date of Patent: April 12, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Akinori Shibuya, Kazuto Kunita
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Patent number: 6855476Abstract: A photoacid compound having the following general structure: R—O(CF2)nSO3X wherein n is an integer between about 1 to 4; R is selected from the group consisting of: substituted or unsubstituted C1-C12 linear or branched alkyl or alkenyl, substituted or unsubstituted araalkyl, substituted or unsubstituted aryl, substituted or unsubstituted bicycloalkyl, substituted or unsubstituted tricycloalkyl, hydrogen, alkyl sulfonic acid, substituted or unsubstituted perfluoroalkyl, the general structure F((CF2)pO)m(CF2)q— wherein p is between about 1 to 4, m is between about 0 to 3 and q is between about 1 to 4, and substituted or unsubstituted partially fluorinated alkyl, halofluoroalkyl, perfluoroalkylsulfonic, or glycidyl; and X is selected from the group consisting of: organic cations and covalently bonded organic radicals.Type: GrantFiled: April 5, 2002Date of Patent: February 15, 2005Assignee: Arch Specialty Chemicals, Inc.Inventors: Lawrence Ferreira, Andrew J. Blakeney, Gregory Dominic Spaziano, Ognian Dimov, J. Thomas Kocab, John P. Hatfield
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Patent number: 6849384Abstract: Photoacid generators comprising sulfonium salt compounds represented by the following general formula (2) wherein R1 and R2 represent each an alkyl group optionally having oxo, or R1 and R2 may be cyclized together to form an alkylene group optionally having oxo; R3, R4 and R5 represent each hydrogen or a linear, branched, monocyclic, polycyclic or crosslinked cyclic alkyl group; and Y? represents a counter ion.Type: GrantFiled: July 23, 2001Date of Patent: February 1, 2005Assignee: NEC CorporationInventors: Shigeyuki Iwasa, Katsumi Maeda, Kaichiro Nakano, Etsuo Hasegawa
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Patent number: 6838225Abstract: A radiation-sensitive resin composition comprising: (A) an acid-dissociable group-containing resin, insoluble or scarcely soluble in alkali but becoming soluble in alkali when the acid-dissociable group dissociates, and containing recurring units with specific structures and (B) a photoacid generator of the formula (3), wherein R5 represents a monovalent aromatic hydrocarbon group, m is 1-8, and n is 0-5. The resin composition is suitable as a chemically-amplified resist responsive to deep ultraviolet rays such as a KrF excimer laser and ArF excimer laser, exhibits high transparency, excellent resolution, dry etching resistance, and sensitivity, produces good pattern shapes, and well adheres to substrates.Type: GrantFiled: January 16, 2002Date of Patent: January 4, 2005Assignee: JSR CorporationInventors: Yukio Nishimura, Masafumi Yamamoto, Atsuko Kataoka, Toru Kajita
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Patent number: 6818375Abstract: Disclosed are photoimageable compositions having improved stripping properties including a photoresist strip enhancer. Also disclosed are methods of enhancing the strippability of photoimageable compositions and methods for manufacturing printed wiring boards using such photoimageable compositions.Type: GrantFiled: November 28, 2001Date of Patent: November 16, 2004Assignee: Eternal Technology CorporationInventors: Thomas A. Koes, Todd Johnson
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Publication number: 20040219457Abstract: A photopolymerisable system is disclosed which can be polymerised by exposure to UV light, for example, to form a solid, light-transmitting sheet material having volume refractive index variations defining an optical diffuser or a hologram, for example. The system includes a silicone monomer, prepolymer, macromonomer or co-monomer capable of undergoing free radical initiated polymerization and further includes a photoinitiator.Type: ApplicationFiled: October 16, 2003Publication date: November 4, 2004Inventors: Robin J.T. Clabburn, Rifat Iqbal, Stephen Moratti
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Patent number: 6806024Abstract: Radically photopolymerizable compositions comprising (a) at least one ethylenically unsaturated photopolymerizable compound; (b) as photoinitiator, at least one compound of formulae (I, II, III, IV, V and/or VI), wherein m is 0 or 1; n is 0, 1, 2 or 3; x is 1 or 2; R1 is inter alia phenyl, naphthyl, anthracyl or phenanthryl, a heteroaryl radical, C2-C12alkenyl, C4-C8cycloalkenyl, or C6-C12bicycloalkenyl; R′1 is inter alia C2-C12alkylene, or phenylene; R2 has one of the meanings of R1 or inter alia is phenyl; y is 1 or 2; R3 if x is 1 inter alia is C1-C18alkylsulfonyl, or phenyl-C1-C3alkylsulfonyl, R3 if x is 2, is for example C2-C12alkylenedisulfonyl; R4 and R5 inter alia are hydrogen, halogen, or C1-C8alkyl; R6, R7, R8 inter alia are hydrogen, R26Y—, or phenyl; R9 inter alia is C5-C8cycloalkyl, or phenyl; A is for example —S—, —O—, or —NR10—; Q is C1-C8-alkylene optionally interrupted by —O—; X is —O— or —NR9—; R10 inter aliaType: GrantFiled: August 27, 2001Date of Patent: October 19, 2004Assignee: Ciba Specialty Chemicals CorporationInventors: Hisatoshi Kura, Hitoshi Yamato, Masaki Ohwa, Kurt Dietliker
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Patent number: 6800420Abstract: A photosensitive thick film composition. The photosensitive thick film composition can produce electrode material with high resolution and high contrast. The photosensitive thick film composition includes an acrylic copolymer, a photoinitiator, a reactive monomer, a conductive metal, glass powder, an additive, and an organic solvent.Type: GrantFiled: December 4, 2002Date of Patent: October 5, 2004Assignee: Industrial Technology Research InstituteInventors: Tsing-Tang Song, Weir-Torn Jiang, Shung-Jim Yang, Sheng-Min Wang, Kom-Bei Shiu
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Publication number: 20040152008Abstract: A method of colouring a polymeric material containing a) a latent acid, b) a colour former and c) optionally further ingredients by irradiation with UV-light.Type: ApplicationFiled: December 4, 2003Publication date: August 5, 2004Inventors: Michael Heneghan, James Philip Taylor
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Patent number: 6767686Abstract: A chemically amplifying type positive resist composition suitable for use in the lithography utilizing an ArF or KrF excimer laser and excellent in the shape of profile is provided, which comprises a resin which has an alkali-soluble group protected by 2-alkyl-2-adamantyl group or 1-adamantyl-1-alkylalkyl group, and which, per se, is insoluble or slightly soluble in alkali but becomes soluble in alkali by the action of an acid; and a sulfonium salt acid generating agent represented by the following formula (I): wherein Q1, Q2 and Q3 independently represent hydrogen, hydroxyl, alkyl having 1 to 6 carbon atoms or alkoxy having 1 to 6 carbon atoms; and Q4 represents perfluoroalkyl which may have a cyclic structure.Type: GrantFiled: November 16, 2001Date of Patent: July 27, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Yasunori Uetani, Kenji Ohashi, Hiroshi Moriuma
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Patent number: 6733951Abstract: A positive radiation-sensitive composition comprising: (A) at least one compound capable of generating an acid upon irradiation with an actinic ray represented by the following formula (I); and (B) a resin having a group capable of decomposing by the action of an acid to increase the solubility in an alkali developing solution: wherein R1, R2, R3, R4 and R5 each represents a hydrogen atom, an alkyl group, an alkoxyl group, a nitro group, a halogen atom, an alkyloxycarbonyl group, or an aryl group, and at least two of R1, R2, R3, R4 and R5 may be bonded to form a cyclic structure; R6 and R7 each represents a hydrogen atom, an alkyl group, a cyano group or an aryl group; Y1 and Y2 each represents an alkyl group, an aryl group, an aralkyl group, or an aromatic group containing a hetero atom, and Y1 and Y2 may be bonded to form a ring; Y3 represents a single bond or a divalent linking group; and X− represents a non-nucleophilic anion; provided that at least one of R1, R2, R3, R4 and R5,Type: GrantFiled: May 14, 2002Date of Patent: May 11, 2004Assignee: Fuji Photo Film Co., Ltd.Inventor: Kunihiko Kodama
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Publication number: 20040076902Abstract: A chemical amplification type positive resist composition, which can attain high sensitivity while maintaining high resolution, and comprises (A) a compound of the following formula (I): 1Type: ApplicationFiled: October 17, 2002Publication date: April 22, 2004Inventors: Junji Nakanishi, Katsuhiko Namba
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Publication number: 20040072097Abstract: A photosensitive composition of the present invention has excellent sensitivity and pattern profile, which comprises an acid generator having a specific structure.Type: ApplicationFiled: September 24, 2003Publication date: April 15, 2004Applicant: FUJI PHOTO FILM CO., LTD.Inventor: Kunihiko Kodama
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Publication number: 20040067431Abstract: A photoreactive composition comprises (a) at least one reactive species that is capable of undergoing an acid- or radical-initiated chemical reaction; and (b) a photoinitiator system comprising photochemically-effective amounts of (1) at least one type of semiconductor nanoparticle quantum dot that has at least one electronic excited state that is accessible by absorption of two or more photons, and (2) a composition, different from said reactive species, that is capable of interacting with the excited state of the semiconductor nanoparticle quantum dot to form at least one reaction-initiating species.Type: ApplicationFiled: October 2, 2002Publication date: April 8, 2004Applicant: 3M Innovative Properties CompanyInventors: David S. Arney, Catherine A. Leatherdale, Manoj Nirmal
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Publication number: 20040053158Abstract: 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-Calkyl, 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 independentlyType: ApplicationFiled: May 21, 2003Publication date: March 18, 2004Inventors: Hitoshi Yamato, Toshikage Asakura, Akira Matsumoto, Masaki Ohwa
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Publication number: 20040033440Abstract: Photoacid generators capable of generating 2,4,6-triisopropylbenzenesulfonic acid upon exposure to actinic radiation are suited for use in chemically amplified positive resist compositions. Due to the low diffusion of 2,4,6-triisopropylbenzenesulfonic acid, the compositions have many advantages including improved resolution, improved focus latitude, and minimized line width variation or shape degradation even on long-term PED.Type: ApplicationFiled: August 8, 2003Publication date: February 19, 2004Inventors: Kazunori Maeda, Youichi Ohsawa, Satoshi Watanabe
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Publication number: 20040009430Abstract: The photosensitive resin composition of the present invention is an excellent photosensitive resin composition: exhibiting significant transmissibility at the use of an exposure light source of 160 nm or less, more specifically F2 excimer laser light , where line edge roughness and development time dependence are small and a problem of footing formation is improved; and comprising a resin which decomposes by an action of acid to increase the solubility in alkali developer, in which the resin contains a specific repeat unit; a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation, in which the compound includes at least two kinds of compounds selected from the group consisting of specific compounds (B1), (B2), (B3) and (B4).Type: ApplicationFiled: June 6, 2003Publication date: January 15, 2004Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Shinichi Kanna, Kazuyoshi Mizutani, Tomoya Sasaki
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Patent number: 6664022Abstract: New photoacid generator compounds (“PAGs”) are provided and photoresist compositions that comprise such compounds. In particular, ionic PAGs are provided that include tri-naphthyl sulfonium, thienyl iodonium, thienyl sulfonium, pentafluorophenyl iodonium and pentafluorophenyl sulfonium compounds. PAGs of the invention are particularly useful as photoactive components of photoresists imaged at short wavelengths such as sub-300 nm, sub-200 nm and sub-160 nm such as 248 nm, 193 nm and 157 nm.Type: GrantFiled: August 25, 2000Date of Patent: December 16, 2003Assignee: Shipley Company, L.L.C.Inventors: James F. Cameron, Gerhard Pohlers
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Publication number: 20030203307Abstract: A radiation-sensitive resin composition comprising: (A) an alkali insoluble or scarcely alkali-soluble resin having an acid-dissociable protecting group of the following formula [I], 1Type: ApplicationFiled: February 21, 2003Publication date: October 30, 2003Inventors: Akimasa Soyano, Hiroyuki Ishii, Hidemitsu Ishida, Motoyuki Shima, Yukio Nishimura
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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