Sulfur In Heterocyclic Ring Patents (Class 430/922)
  • Patent number: 7560219
    Abstract: 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: Grant
    Filed: April 26, 2007
    Date of Patent: July 14, 2009
    Assignee: Henkel AG & Co. KGaA
    Inventors: Yuxia Liu, Donald E. Herr
  • Patent number: 7550253
    Abstract: 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: Grant
    Filed: February 16, 2005
    Date of Patent: June 23, 2009
    Assignee: Panasonic Corporation
    Inventors: Masayuki Endo, Masaru Sasago
  • Patent number: 7541131
    Abstract: 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: Grant
    Filed: February 17, 2006
    Date of Patent: June 2, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Yasutomo Kawanishi
  • Patent number: 7531286
    Abstract: 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: Grant
    Filed: March 13, 2003
    Date of Patent: May 12, 2009
    Assignee: JSR Corporation
    Inventors: Yukio Nishimura, Hiroyuki Ishii, Masafumi Yamamoto, Isao Nishimura
  • Patent number: 7527913
    Abstract: 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: Grant
    Filed: January 24, 2008
    Date of Patent: May 5, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Young-Gil Kwon, Young-Ho Kim, Do-Young Kim, Jae-Hee Choi, Se-Kyung Baek
  • Patent number: 7524611
    Abstract: 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: Grant
    Filed: September 26, 2007
    Date of Patent: April 28, 2009
    Assignee: University of Central Florida Research Foundation, Inc.
    Inventor: Kevin D. Belfield
  • Patent number: 7521168
    Abstract: 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: Grant
    Filed: February 11, 2003
    Date of Patent: April 21, 2009
    Assignee: Fujifilm Corporation
    Inventors: Kazuyoshi Mizutani, Hyou Takahashi
  • Patent number: 7510822
    Abstract: 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: Grant
    Filed: April 9, 2003
    Date of Patent: March 31, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7498126
    Abstract: 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: Grant
    Filed: June 5, 2007
    Date of Patent: March 3, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Kazunori Maeda, Satoshi Watanabe
  • Patent number: 7491485
    Abstract: 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 carbon
    Type: Grant
    Filed: May 20, 2008
    Date of Patent: February 17, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Komei Hirahara
  • Patent number: 7491484
    Abstract: 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: Grant
    Filed: October 10, 2007
    Date of Patent: February 17, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Young-Gil Kwon, Do-Young Kim, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim
  • Patent number: 7488568
    Abstract: 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: Grant
    Filed: April 1, 2008
    Date of Patent: February 10, 2009
    Assignee: 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
  • Patent number: 7465528
    Abstract: 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: Grant
    Filed: October 17, 2006
    Date of Patent: December 16, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Fumiyuki Nishiyama, Kunihiko Kodama
  • Patent number: 7396899
    Abstract: 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: Grant
    Filed: December 22, 2006
    Date of Patent: July 8, 2008
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Airi Yamada, Yasunori Uetani, Akira Kamabuchi
  • Patent number: 7390613
    Abstract: 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: Grant
    Filed: December 4, 2006
    Date of Patent: June 24, 2008
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: M. Dalil Rahman, David L. Rentkiewicz
  • Patent number: 7387865
    Abstract: 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: Grant
    Filed: July 20, 2004
    Date of Patent: June 17, 2008
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sung-ouk Jung, Seung-ju Seo, Jae-chan Park
  • Patent number: 7378223
    Abstract: 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: Grant
    Filed: May 6, 2005
    Date of Patent: May 27, 2008
    Assignee: Dongjin Semichem, Co., Ltd.
    Inventors: Bong-gi Kim, Sung-mun Ryu, Seong-mo Park, Chan-seok Park
  • Patent number: 7371503
    Abstract: 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: Grant
    Filed: January 9, 2004
    Date of Patent: May 13, 2008
    Assignee: JSR Corporation
    Inventors: Takashi Miyamatsu, Hirokazu Niwata, Satoshi Ebata, Yong Wang
  • Patent number: 7288363
    Abstract: 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: Grant
    Filed: April 14, 2005
    Date of Patent: October 30, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ryuji Koitabashi, Satoshi Watanabe, Youichi Ohsawa
  • Patent number: 7223518
    Abstract: 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: Grant
    Filed: June 7, 2004
    Date of Patent: May 29, 2007
    Assignee: Georgia Tech Research Corporation
    Inventors: Clifford L. Henderson, Trevor Hoskins, Cody M. Berger
  • Patent number: 7214465
    Abstract: 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: Grant
    Filed: January 9, 2003
    Date of Patent: May 8, 2007
    Assignee: Fujifilm Corporation
    Inventors: Hajime Nakao, Yasumasa Kawabe, Toru Fujimori, Kunihiko Kodama
  • Patent number: 7160667
    Abstract: 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: Grant
    Filed: January 21, 2004
    Date of Patent: January 9, 2007
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Kaoru Iwato
  • Patent number: 7160669
    Abstract: 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: Grant
    Filed: October 10, 2003
    Date of Patent: January 9, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Airi Yamada, Yasunori Uetani, Akira Kamabuchi
  • Patent number: 7122294
    Abstract: 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: Grant
    Filed: May 22, 2003
    Date of Patent: October 17, 2006
    Assignee: 3M Innovative Properties Company
    Inventor: William M. Lamanna
  • Patent number: 7094515
    Abstract: 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: Grant
    Filed: March 15, 2004
    Date of Patent: August 22, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kunihiko Kodama, Hyou Takahashi
  • Patent number: 7081326
    Abstract: 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: Grant
    Filed: March 11, 2004
    Date of Patent: July 25, 2006
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara R. Varanasi
  • Patent number: 7078148
    Abstract: 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: Grant
    Filed: May 29, 2003
    Date of Patent: July 18, 2006
    Assignee: JSR Corporation
    Inventors: Motoyuki Shima, Hiroyuki Ishii, Atsushi Nakamura, Masafumi Yamamoto
  • Patent number: 7033727
    Abstract: A photosensitive composition of the present invention has excellent sensitivity and pattern profile, which comprises an acid generator having a specific structure.
    Type: Grant
    Filed: September 24, 2003
    Date of Patent: April 25, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Kunihiko Kodama
  • Patent number: 6929896
    Abstract: 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 ea
    Type: Grant
    Filed: November 26, 2001
    Date of Patent: August 16, 2005
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Hitoshi Yamato, Toshikag Asakura, Akira Matsumoto, Masaki Ohwa
  • Patent number: 6927009
    Abstract: 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: Grant
    Filed: May 21, 2002
    Date of Patent: August 9, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kunihiko Kodama, Kenichiro Sato, Toru Fujimori
  • Patent number: 6878505
    Abstract: 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: Grant
    Filed: May 28, 2002
    Date of Patent: April 12, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Akinori Shibuya, Kazuto Kunita
  • Patent number: 6855476
    Abstract: 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: Grant
    Filed: April 5, 2002
    Date of Patent: February 15, 2005
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Lawrence Ferreira, Andrew J. Blakeney, Gregory Dominic Spaziano, Ognian Dimov, J. Thomas Kocab, John P. Hatfield
  • Patent number: 6849384
    Abstract: 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: Grant
    Filed: July 23, 2001
    Date of Patent: February 1, 2005
    Assignee: NEC Corporation
    Inventors: Shigeyuki Iwasa, Katsumi Maeda, Kaichiro Nakano, Etsuo Hasegawa
  • Patent number: 6838225
    Abstract: 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: Grant
    Filed: January 16, 2002
    Date of Patent: January 4, 2005
    Assignee: JSR Corporation
    Inventors: Yukio Nishimura, Masafumi Yamamoto, Atsuko Kataoka, Toru Kajita
  • Patent number: 6818375
    Abstract: 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: Grant
    Filed: November 28, 2001
    Date of Patent: November 16, 2004
    Assignee: Eternal Technology Corporation
    Inventors: Thomas A. Koes, Todd Johnson
  • Publication number: 20040219457
    Abstract: 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: Application
    Filed: October 16, 2003
    Publication date: November 4, 2004
    Inventors: Robin J.T. Clabburn, Rifat Iqbal, Stephen Moratti
  • Patent number: 6806024
    Abstract: 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 alia
    Type: Grant
    Filed: August 27, 2001
    Date of Patent: October 19, 2004
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Hisatoshi Kura, Hitoshi Yamato, Masaki Ohwa, Kurt Dietliker
  • Patent number: 6800420
    Abstract: 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: Grant
    Filed: December 4, 2002
    Date of Patent: October 5, 2004
    Assignee: Industrial Technology Research Institute
    Inventors: Tsing-Tang Song, Weir-Torn Jiang, Shung-Jim Yang, Sheng-Min Wang, Kom-Bei Shiu
  • Publication number: 20040152008
    Abstract: 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: Application
    Filed: December 4, 2003
    Publication date: August 5, 2004
    Inventors: Michael Heneghan, James Philip Taylor
  • Patent number: 6767686
    Abstract: 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: Grant
    Filed: November 16, 2001
    Date of Patent: July 27, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Kenji Ohashi, Hiroshi Moriuma
  • Patent number: 6733951
    Abstract: 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: Grant
    Filed: May 14, 2002
    Date of Patent: May 11, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Kunihiko Kodama
  • Publication number: 20040076902
    Abstract: 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): 1
    Type: Application
    Filed: October 17, 2002
    Publication date: April 22, 2004
    Inventors: Junji Nakanishi, Katsuhiko Namba
  • Publication number: 20040072097
    Abstract: A photosensitive composition of the present invention has excellent sensitivity and pattern profile, which comprises an acid generator having a specific structure.
    Type: Application
    Filed: September 24, 2003
    Publication date: April 15, 2004
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventor: Kunihiko Kodama
  • Publication number: 20040067431
    Abstract: 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: Application
    Filed: October 2, 2002
    Publication date: April 8, 2004
    Applicant: 3M Innovative Properties Company
    Inventors: David S. Arney, Catherine A. Leatherdale, Manoj Nirmal
  • Publication number: 20040053158
    Abstract: 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 independently
    Type: Application
    Filed: May 21, 2003
    Publication date: March 18, 2004
    Inventors: Hitoshi Yamato, Toshikage Asakura, Akira Matsumoto, Masaki Ohwa
  • Publication number: 20040033440
    Abstract: 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: Application
    Filed: August 8, 2003
    Publication date: February 19, 2004
    Inventors: Kazunori Maeda, Youichi Ohsawa, Satoshi Watanabe
  • Publication number: 20040009430
    Abstract: 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: Application
    Filed: June 6, 2003
    Publication date: January 15, 2004
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Shinichi Kanna, Kazuyoshi Mizutani, Tomoya Sasaki
  • Patent number: 6664022
    Abstract: 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: Grant
    Filed: August 25, 2000
    Date of Patent: December 16, 2003
    Assignee: Shipley Company, L.L.C.
    Inventors: James F. Cameron, Gerhard Pohlers
  • Publication number: 20030203307
    Abstract: 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], 1
    Type: Application
    Filed: February 21, 2003
    Publication date: October 30, 2003
    Inventors: Akimasa Soyano, Hiroyuki Ishii, Hidemitsu Ishida, Motoyuki Shima, Yukio Nishimura
  • Publication number: 20030198894
    Abstract: 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: Application
    Filed: February 11, 2003
    Publication date: October 23, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Kazuyoshi Mizutani, Hyou Takahashi