Cationic Or Anionic Patents (Class 430/914)
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Patent number: 7049044Abstract: The present invention provides new high resolution nanocomposite resists applicable to next generation lithographies, methods of making these novel resists, and methods of using these new resists in lithographic processes to effect state-of-the-art lithographies. New nanocomposite negative resists comprising a photoacid generating component, a styrene component, and an optional polyhedral oligosilsequioxane component are provided. Negative resists of this invention may also contain an optional methacrylate component. This invention and the embodiments described herein constitute fundamentally new architectures for high resolution resists.Type: GrantFiled: December 19, 2002Date of Patent: May 23, 2006Assignee: The University of North Carolina at CharlotteInventors: Kenneth Gonsalves, Mohammed Azam Ali
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Patent number: 7041426Abstract: A photoresist includes a polymer which has acid-cleavable groups in its main chain. The polymer can thus be cleaved by acid into short cleavage products which can be removed from the substrate through the use of a developer. The polymer is completely or partially fluorinated, and consequently has an improved transparency to light of short wavelengths.Type: GrantFiled: July 19, 2002Date of Patent: May 9, 2006Assignee: Infineon Technologies AGInventors: Christian Eschbaumer, Christoph Hohle, Michael Sebald, Jörg Rottstegge
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Patent number: 7041428Abstract: A pattern formation material of this invention contains a base polymer including a unit represented by Chemical Formula 1 and, and an acid generator: Chemical Formula 1: wherein R1 is a hydrogen atom, a chlorine atom, a fluorine atom, an alkyl group or an alkyl group including a fluorine atom; and R2 is a protecting group released by an acid.Type: GrantFiled: September 12, 2002Date of Patent: May 9, 2006Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Tsuyohiko Fujigaya
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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: 7033728Abstract: The present invention relates to a photosensitive composition useful at wavelengths between 300 nm and 10 nm which comprises a polymer containing a substituted or unsubstituted higher adamantane.Type: GrantFiled: December 29, 2003Date of Patent: April 25, 2006Assignee: AZ Electronic Materials USA Corp.Inventor: Ralph R. Dammel
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Patent number: 7029808Abstract: A radiation-sensitive coating material, in addition to a base polymer, has a solvent and a radiation-active substance which forms an acid on irradiation by light (including energetic electrons or ions), a fluorescent substance which alters its fluorescence property subject to a change in the acid content of its surroundings. In a process for exposing a substrate coated with the coating material at least one sensor in the exposure chamber of the exposure apparatus measures the intensity of the change in fluorescence spectrum as a function of time during the exposure operation. From the course of intensity at the time of an individual line of the fluorescence spectrum or the intensity integrated over a wavelength interval it is possible to determine the endpoint of the exposure operation by way of electronic algorithms. Deviations from experimentally determined ideal curves of the intensity course provide information on erroneous functions in the course of coating material application and exposure.Type: GrantFiled: September 29, 2003Date of Patent: April 18, 2006Assignee: Infineon Technologies AGInventors: Jenspeter Rau, Siegfried Schwarzl, Stefan Wurm
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Patent number: 7022457Abstract: The present invention pertains to photoimaging and the use of photoresists (positive-working and/or negative-working) for imaging in the production of semiconductor devices. The present invention also pertains to novel hydroxy ester-containing polymer compositions that are useful as base resins in resists and potentially in many other applications.Type: GrantFiled: September 24, 2003Date of Patent: April 4, 2006Assignee: E. I. du Pont de Nemours and CompanyInventors: William Brown Farnham, Andrew Edward Feiring, Frank Leonard Schadt, III, Weiming Qiu
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Patent number: 7011923Abstract: A negative photoresist composition and a method of patterning a substrate through use of the negative photoresist composition. The negative photoresist composition comprises a radiation sensitive acid generator, a first polymer containing an alkoxymethyl amido group and a hydroxy-containing second polymer. The first and second polymers may also have a repeating unit having an aqueous base soluble moiety. The first and second polymers undergo acid catalyzed crosslinking upon exposure of the acid to radiation, producing a product that is insoluble in an aqueous alkaline developer solution.Type: GrantFiled: April 7, 2004Date of Patent: March 14, 2006Assignee: International Business Machines CorporationInventors: Wenjie Li, Pushkara R. Varanasi
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Patent number: 7008749Abstract: The present invention provides new high resolution resists applicable to next generation lithographies, methods of making these novel resists, and methods of using these new resists in lithographic processes to effect state-of-the-art lithographies. New nanocomposite resists comprising nanoparticles in a polymer matrix are provided in this invention. New chemically amplified resists that incorporate inorganic moieties as part of the polymer are presented herein, as are new chemically amplified resists that incorporate photoacid generating groups within the polymeric chain. Novel non-chemically amplified yet photosensitive resists, and new organic-inorganic hybrid resists are also provided herein. This invention and the embodiments described herein constitute fundamentally new architectures for high resolution resists.Type: GrantFiled: November 5, 2001Date of Patent: March 7, 2006Assignee: The University of North Carolina at CharlotteInventor: Kenneth E. Gonsalves
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Patent number: 7001706Abstract: A sulfonate of the formula (I): wherein Q1, Q2, Q3, Q4 and Q5 each independently represents a certain substituent, and A+ represents a counter ion, with the proviso that at least one of Q1, Q2, Q3, Q4 and Q5 is a group of the formula (II) wherein R1 and R2 each independently an alkyl having 1 to 12 carbon atoms or the like; and a chemical amplification type positive resist composition comprising the sulfate of the formula (I) and a 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: July 16, 2004Date of Patent: February 21, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Makoto Akita, Isao Yoshida
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Patent number: 6994946Abstract: Novel silicon-containing polymers are provided comprising recurring units having a POSS pendant and units which improve alkali solubility under the action of an acid. Resist compositions comprising the polymers are sensitive to high-energy radiation and have a high sensitivity and resolution at a wavelength of up to 300 nm and improved resistance to oxygen plasma etching.Type: GrantFiled: May 26, 2004Date of Patent: February 7, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Takanobu Takeda
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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: 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: 6991888Abstract: The present invention relates to a novel photoresist composition that can be developed with an aqueous alkaline solution, and is capable of being imaged at exposure wavelengths in the deep ultraviolet. The invention also relates to a process for imaging the novel photoresist as well as novel photoacid generators. The novel photoresist comprises a) a polymer containing an acid labile group, and b) a novel mixture of photoactive compounds, where the mixture comprises a lower absorbing compound selected from structure 1 and 2, and a higher absorbing compound selected from structure 4 and 5, where, R1 and R2 R5, R6, R7, R8, and R9 are defined herein; m=1–5; X? is an anion, and Ar is selected from naphthyl, anthracyl, and structure 3, where R30, R31, R32, R33, and R34 are defined herein.Type: GrantFiled: May 16, 2003Date of Patent: January 31, 2006Assignee: AZ Electronic Materials USA Corp.Inventors: Munirathna Padmanaban, Takanori Kudo, Sangho Lee, Ralph R. Dammel, M. Dalil Rahman
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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: 6977131Abstract: A radiation-sensitive patterning composition comprising: (1) at least one acid generating compound selected from the group of compounds of formulae (I) or (II): wherein R1, R2, R3, R4, R5, and R6, are individually selected from the group consisting of a hydrogen atom, nitro group, hydroxyl group, a carbonyl group, a halogen atom, a cyano group and an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group; an unsubstituted or substituted alkoxy group, or an unsubstituted or substituted aryl group; wherein X+ represents an onium ion selected from the group consisting of diazonium, iodonium, sulfonium, phosphonium, bromonium, chloronium, oxysulfoxonium, oxysulfonium, sulfoxonium, selenium, tellurium and arsenium; and wherein n is an integer from 4 to 100; (2) at least one cross-linking agent cross-linkable by an acid; (3) at least one polymer compound capable of reacting with the cross-linking agent; and (4) at least one infrared absorbing compound.Type: GrantFiled: May 30, 2002Date of Patent: December 20, 2005Assignee: Kodak Polychrome Graphics LLCInventor: Ting Tao
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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: 6969576Abstract: A photoresist composition that employs onium salt carboxylates as thermally stable dissolution inhibitors. The photoresist composition can be either an onium carboxylate salt with a phenolic photoresist, such as novolac, or an onium cation protected carboxylate-containing resin such as an acrylic/acrylic acid copolymer. The onium carboxylate can be an onium cholate, wherein the onium cholate is an iodonium cholate. Particularly preferred iodonium cholates are alkyloxyphenylphenyl iodonium cholates and most particularly preferred is octyloxyphenyphenyl iodonium cholate. The photoresist composition will not create nitrogen or other gaseous byproducts upon exposure to radiation, does not require water for photoactivation, has acceptable UV radiation transmission characteristics, and is thermally stable at temperatures required for solvent removal.Type: GrantFiled: November 30, 2001Date of Patent: November 29, 2005Assignee: Sandia National LaboratoriesInventors: Paul M. Dentinger, Kelby L. Simison
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Patent number: 6962768Abstract: Provided are a variety of monomers suitable of producing photosensitive polymers, that are in turn, useful in photoresist compositions, through radical (cationic) polymerization including at least one multi-ring alkenyl ethers and one ?-fluorinated acrylate. The resulting photoresist compositions exhibit both acceptable resistance to dry etching processing and light transmittance suitable for use with various light sources such as KrF excimer lasers, ArF excimer lasers or F2 excimer lasers, in a photolithography process to produce fine photoresist patterns. In addition to the multi-ring alkenyl ethers and ?-fluorinated acrylates, additional monomers comprising one or more cyclic aliphatic and heterocyclic compounds, both unsubstituted and substituted, in particular dihydropyrans, may be incorporated into the photosensitive polymers.Type: GrantFiled: March 12, 2004Date of Patent: November 8, 2005Assignee: Samsung Electronics Co., Ltd.Inventors: Hyun-Woo Kim, Sang-Gyun Woo
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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: 6936401Abstract: The pattern formation material of this invention is a chemically amplified resist material including a polymer whose solubility in a developer is changed in the presence of an acid; an acid generator for generating an acid through irradiation with exposing light; and a base generator for generating a base through irradiation with the exposing light. The base generator is more photosensitive to longer band light of a wavelength longer than extreme UV than to extreme UV when irradiated, as the exposing light, with the extreme UV and the longer band light at equivalent exposure energy.Type: GrantFiled: July 2, 2003Date of Patent: August 30, 2005Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Masayuki Endo, Masaru Sasago
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Patent number: 6933097Abstract: A photosensitive composition for optical waveguides comprising of an organic oligomer, a polymerization initiator and a crosslinking agent, the organic oligomer being a silicone oligomer represented by the following formula (1), wherein X denotes hydrogen, deuterium, halogen, an alkyl group or an alkoxy group; m is an integer from 1 to 5; x and y represent the proportion of respective units, and neither x nor y is 0; and R1 denotes a methyl, ethyl, or isopropyl group; a production method thereof, and a polymer optical waveguide pattern formation method using the same.Type: GrantFiled: March 18, 2004Date of Patent: August 23, 2005Assignee: Nippon Telegraph and Telephone CorporationInventors: Seiji Toyoda, Saburo Imamura, Satoru Tomaru, Takashi Kurihara, Koji Enbutsu, Shoichi Hayashida, Tohru Maruno
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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: 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: 6919160Abstract: Disclosed herein is an acrylic compound that can be polymerized by itself or with at least one other ethylenically unsaturated monomer to provide a polymer. The polymer may be used, for example, within a sub-200 nm photoresist composition. Also disclosed is a method to make the acrylic compound of the present invention from the raw material trifluoroacetone.Type: GrantFiled: February 20, 2003Date of Patent: July 19, 2005Assignee: Air Products and Chemicals, Inc.Inventors: Atteye Houssein Abdourazak, Thomas John Markley
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Patent number: 6919159Abstract: The present invention provides a photopolymerizable composition, which is highly sensitive to visible light rays to IR rays and has an excellent raw storage property, and a recording material capable of carrying out highly sensitive image recording and having an excellent raw storage property and humidity dependency. Namely, the invention provides a photopolymerizable composition containing at least a polymerizable compound having an ethylenic unsaturated bond, a photoradical generating agent, and a thiol compound represented by the following general formula (I) and a recording material using the photopolymerizable composition: [R represents an alkyl or an aryl, either of which may have substituents; A represents an atom group forming a 5-member or 6-member heteroring having an N?C—N portion and carbon atoms and A may further have a substituent group.].Type: GrantFiled: October 7, 2002Date of Patent: July 19, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Hirotaka Matsumoto, Shintaro Washizu, Kazunori Nigorikawa
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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: 6908722Abstract: A novel photoacid generator containing a structure of the following formula (I), wherein R is a monovalent organic group with a fluorine content of 50 wt % or less, a nitro group, a cyano group, or a hydrogen atom, and Z1 and Z2 are individually a fluorine atom or a linear or branched perfluoroalkyl group having 1-10 carbon atoms, is provided. When used in a chemically amplified radiation-sensitive resin composition, the photoacid generator exhibits high transparency, comparatively high combustibility, and no bioaccumulation, and produces an acid exhibiting high acidity, high boiling point, moderately short diffusion length in the resist coating, and low dependency to mask pattern density.Type: GrantFiled: June 28, 2002Date of Patent: June 21, 2005Assignee: JSR CorporationInventors: Satoshi Ebata, Eiji Yoneda, Tomoki Nagai, Tatsuya Toneri, Yong Wang, Haruo Iwasawa, Yukio Nishimura
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Patent number: 6902862Abstract: A negative type resist composition comprising: (A1) a compound generating a sulfonic acid upon irradiation with actinic rays or a radiation and having the specific formula, (A2) a compound generating a sulfonic acid upon irradiation with actinic rays or a radiation and having the specific structure, (B) an alkali-soluble resin, and (C) a crosslinking agent capable of carrying out an addition reaction with the alkali-soluble resin which is the component (B) by the action of an acid.Type: GrantFiled: September 5, 2003Date of Patent: June 7, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Hyou Takahashi, Kazuyoshi Mizutani, Shoichiro Yasunami
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Patent number: 6902875Abstract: A finely patterned silica type ceramic film suitable as an inter-layer dielectric is formed in a short time by applying, onto a substrate, a positive working radiation sensitive polysilazane composition comprising a modified poly(sil sesquiazane) having a number average molecular weight of 100 to 100,000 and containing a basic constituent unit represented by the general formula: —[SiR6(NR7)1.5]— and other constituent units represented by the general formula: —[SiR62NR7]— and/or —[SiR63(NR7)0.5]— (R6 and R7 independently represent a hydrogen atom, a C1-3 alkyl group or a substituted or unsubstituted phenyl group) in a ratio of 0.Type: GrantFiled: August 24, 2001Date of Patent: June 7, 2005Assignee: Clariant Finance (BVI) LimitedInventors: Tatsuro Nagahara, Hideki Matsuo
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Patent number: 6899989Abstract: A radiation-sensitive resin composition comprising (A) a photoacid generator such as 2,4,6-trimethylphenyldiphenylsulfonium 2,4-difluorobenzenesulfonate or 2,4,6-trimethylphenyldiphenylsulfonium 4-trifluoromethylbenzenesulfonate and (B) a resin having an acetal structure typified by a poly(p-hydroxystyrene) resin in which a part of hydrogen atoms of phenolic hydroxyl groups have been replaced by 1-ethoxyethyl groups, 1-ethoxyethyl groups and t-butoxycarbonyl groups, or 1-ethoxyethyl groups and t-butyl groups. The resin composition is sensitive to deep ultraviolet rays and charged particles such as electron beams, exhibits excellent resolution performance and pattern shape-forming capability, and suppresses a nano-edge roughness phenomenon to a minimal extent.Type: GrantFiled: November 16, 2001Date of Patent: May 31, 2005Assignee: JSR CorporationInventors: Aki Suzuki, Makoto Murata, Hiromichi Hara, Eiichi Kobayashi
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Patent number: 6897005Abstract: There are provided a photosensitive polymer having a copolymer of alkyl vinyl ether and a resist composition containing the same. The photosensitive polymer includes a copolymer of alkyl vinyl ether and maleic anhydride, represented by the following structure: wherein X is one of a linear alkyl vinyl ether and a cyclic alkyl vinyl ether, which are respectively represented by the structures wherein y is one of the integer values 1 through 4, R1 is one of a hydrogen atom and a methyl group, R2 is a C1 to C20 hydrocarbon, and R3 is one of a hydrogen atom, a C1 to C3 alkyl group and an alkoxy group.Type: GrantFiled: November 12, 2003Date of Patent: May 24, 2005Assignee: Samsung Electronics, Co., Ltd.Inventors: Sang-jun Choi, Hyun-woo Kim
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Patent number: 6893793Abstract: The photosensitive polymer includes a first monomer which is norbornene ester having C1 to C12 aliphatic alcohol as a substituent, and a second monomer which is maleic anhydride. A chemically amplified photoresist composition, containing the photosensitive polymer, has an improved etching resistance and adhesion to underlying layer materials, and exhibits wettability to developing solutions.Type: GrantFiled: March 10, 2003Date of Patent: May 17, 2005Assignee: Samsung Electronics Co., Ltd.Inventors: Dong-won Jung, Sang-jun Choi, Si-hyeung Lee, Sook Lee
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Patent number: 6893795Abstract: A positive working lithographic printing plate precursor comprising a lower layer containing a water-insoluble and alkali-soluble resin, and an upper heat-sensitive layer containing a water-insoluble and alkali-soluble resin and an infrared absorbing dye and increasing the solubility in an alkaline aqueous solution by heating, provided in this order on a hydrophilic support, and (a) the upper heat-sensitive layer containing at least two kinds of surface active agents, or (b) the lower layer and upper heat-sensitive layer each containing a surface active agent different from each other.Type: GrantFiled: July 9, 2002Date of Patent: May 17, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Ikuo Kawauchi, Akio Oda, Hideo Miyake
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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: 6887647Abstract: A negative-working resist composition for electron beams or X-rays comprising (A) a compound generating a sulfonic acid by the irradiation of electron beams or x-rays, (B) a resin which is insoluble in water and soluble in an alkali aqueous solution, (C) a crosslinking agent crosslinking with the resin (B) by the action of an acid, and (D) a compound generating a carboxylic acid having a specific structure by the irradiation of electron beams or x-rays.Type: GrantFiled: March 20, 2002Date of Patent: May 3, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Shoichiro Yasunami, Koji Shirakawa, Yutaka Adegawa
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Patent number: 6887645Abstract: A negative resist composition comprises: (A) an alkali-soluble resin; (B) a compound capable of generating an acid upon irradiation with a radiation; (C) a crosslinking agent capable of crosslinking by the action of an acid; and (D) a solvent mixture containing: at least one solvent selected from the group A below; and at least one selected from the group consisting of the group B below and the group C below: group A: a propylene glycol monoalkyl ether carboxylate; group B: a propylene glycol monoalkyl ether, an alkyl lactate, an acetic ester, a chain ketone and an alkyl alkoxypropionate; group C: a ?-butyrolactone, an ethylene carbonate and a propylene carbonate.Type: GrantFiled: August 31, 2001Date of Patent: May 3, 2005Assignee: Fuji Photo Film Co., Ltd.Inventor: Kazuya Uenishi
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Patent number: 6878502Abstract: A positive resist composition comprises (A) a resin which comprises a specified repeating units and (B) a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation.Type: GrantFiled: July 2, 2002Date of Patent: April 12, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuyoshi Mizutani, Shinichi Kanna
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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: 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: 6861199Abstract: TIMD (tetraisopropyl methylene diphosphonate) as a light absorbance depressant to a light source of a wavelength of less than 200 nm, and a photoresist composition containing the same are disclosed. The disclosed chemically amplified photoresist composition containing TIMD is useful for a VUV (vacuum ultraviolet) photoresist composition due to its low light absorbance to a light source of a wavelength of 157 nm.Type: GrantFiled: June 30, 2003Date of Patent: March 1, 2005Assignee: Hynix SemiconductorInventor: Geun Su Lee
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Patent number: 6858378Abstract: The use of photoacid generators including an alkoxyphenylphenyliodonium salt and/or bis(t-butylphenyl)iodonium salt in a photoimageable composition helps improve resolution. Suitable photoimageable compositions includes: (a) a multifuctional polymeric epoxy resin that is dissolved in an organic solvent wherein the epoxy resin comprises oligomers of bisphenol A that is quantitatively protected by glycidyl ether and wherein the oligomers have an average functionality that ranges from about 3 to 12; and a photoacid generator comprising an alkoxyphenylphenyliodonium salt and/or bis(t-butylphenyl)iodonium salt. Preferred alkoxyphenylphenyliodonium salts include 4-octyloxyphenyl phenyliodonium hexafluoroantimonate and 4-methoxyphenyl phenyliodonium hexafluoroantimonate. The photoimageable composition is particularly suited for producing high aspect ratio microstructures.Type: GrantFiled: April 17, 2002Date of Patent: February 22, 2005Assignee: Sandia National LaboratoriesInventors: Paul Dentinger, Karen L. Krafick, Kelby Liv Simison
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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: 6849382Abstract: A photosensitive polymer including silicon and a resist composition using the same are disclosed. The photosensitive polymer has the following formula 1. In formula 1, R1 of the first monomer and R3 of the third monomer are an alkyl group. R2 of the first monomer is hydrogen, alkyl, alkoxy, or carbonyl. The X of the first monomer is an integer selected from 1 to 4. Further, m/(m+n+p) is about 0.1 to about 0.4, n/(m+n+p) is about 0.1 to about 0.5, and p/(m+n+p) is about 0.1 to about 0.4.Type: GrantFiled: November 25, 2003Date of Patent: February 1, 2005Assignee: Samsung Electronics Co., LTDInventor: Sang-Jun Choi
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Patent number: 6849374Abstract: This invention relates to new photoacid generator compounds and photoresist compositions that comprise such compounds. In particular, the invention relates to photoacid generator compounds that generate an ?,?-difluoroalkyl sulfonic acid upon exposure to activating radiation. Positive- and negative-acting chemically amplified resists that contain such PAGs are particularly preferred. The invention also includes methods for synthesis of such PAGs and ?,?-difluoroalkyl sulfonic acids.Type: GrantFiled: November 3, 2001Date of Patent: February 1, 2005Assignee: Shipley Company, L.L.C.Inventors: James F. Cameron, Thomas M. Zydowsky
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Patent number: 6849377Abstract: Photoresists and associated processes for microlithography in the extreme, far, and near UV are disclosed. The photoresists in some embodiments comprise (a) a fluorine-containing copolymer derived from at least one polycyclic ethylenically unsaturated compound and at least one compound having at least one fluorine atom covalently attached to an ethylenically unsaturated carbon atom; and (b) at least one photoactive component. In other embodiments, the photoresists comprise a fluorine-containing copolymer derived from at least one polycyclic ethylenically unsaturated compound having at least one atom or group covalently attached to a carbon atom contained within a ring structure and separated from each ethylenically unsaturated carbon atom of the ethylenically unsaturated compound by at least one covalently attached carbon atom, wherein the atom or group is selected from the group consisting of fluorine perfluoroalkyl and perfluoroalkoxy.Type: GrantFiled: March 27, 2002Date of Patent: February 1, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Frank L. Schadt, III
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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: 6846605Abstract: The present invention provides a photopolymerizable composition and a recording material using the photopolymerizable composition, which contains a polymerizable compound having an ethylenic unsaturated group, an organic borate and a cationic compound that interacts with the organic borate. The organic borate is represented by the following formula (1) wherein R1 represents an alkyl group, R2 represents an electron-donating group, R3 to R6 each represent a hydrogen atom or a substituent, the sum of Hammett's substituent constants ? of R2 to R6 is 0 to 1, and Z+ represents a group that can form a cation. The organic borate has a melting point of no more than 100° C.Type: GrantFiled: April 24, 2003Date of Patent: January 25, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Yūuichi Fukushige, Yoshimitsu Arai, Masatoshi Yumoto
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Patent number: 6844135Abstract: A chemically amplified resist material comprising a base resin and a photo acid generator having sensitivity at the wavelength of patterning exposure; wherein, the chemically amplified resist material further comprising an activator that generates an acid or a radical by a treatment other than the patterning exposure. A patterning method using the same is also disclosed.Type: GrantFiled: July 8, 2003Date of Patent: January 18, 2005Assignee: Fujitsu LimitedInventors: Junichi Kon, Koji Nozaki, Ei Yano