Pattern Elevated In Radiation Unexposed Areas Patents (Class 430/326)
-
Patent number: 8993212Abstract: A resist composition according to the present invention includes at least a base resin, a photoacid generator and a solvent, wherein the photoacid generator comprises a fluorine-containing sulfonic acid salt of the following general formula (4). In the formula, X independently represents a hydrogen atom or a fluorine atom; n represents an integer of 1 to 6; R1 represents a hydrogen atom, or an alkyl, alkenyl, oxoalkyl, aryl or aralkyl group; any of hydrogen atoms on carbons in R1 may be substituted with a substituent; R2 represents RAO or RBRCN; and A represents a divalent group. This fluorine-containing sulfonic acid salt can serve as a photoacid generator having high solubility in a resist solvent and thus can suitably be used for a resist composition such that the resist composition shows high resolution, wide DOF, small LER and high sensitivity to form a good pattern shape in lithographic processes.Type: GrantFiled: October 14, 2011Date of Patent: March 31, 2015Assignee: Central Glass Company, LimitedInventors: Ryozo Takihana, Satoru Narizuka
-
Patent number: 8993210Abstract: A salt represented by the formula (I): wherein R1 and R2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group which can have one or more fluorine atoms and in which one or more —CH2— can be replaced by —O— or —CO—, R3 represents a group having a cyclic ether structure, and Z1+ represents an organic cation.Type: GrantFiled: February 15, 2011Date of Patent: March 31, 2015Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Hiromu Sakamoto
-
Patent number: 8987386Abstract: A method of producing a polymeric compound containing a structural unit that decomposes upon exposure to generate an acid, the method including: synthesizing a precursor polymer by polymerizing a water-soluble monomer having an anionic group, washing the precursor polymer with water, and subsequently subjecting the precursor polymer to a salt exchange with an organic cation. Also, a polymeric compound produced using the method of producing a polymeric compound, and a method of forming a resist pattern using the resist composition.Type: GrantFiled: June 8, 2012Date of Patent: March 24, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoshiyuki Utsumi, Takahiro Dazai, Masatoshi Arai, Takaaki Kaiho
-
Patent number: 8986921Abstract: A lithographic material stack including a metal-compound hard mask layer is provided. The lithographic material stack includes a lower organic planarizing layer (OPL), a dielectric hard mask layer, and the metal-compound hard mask layer, an upper OPL, an optional anti-reflective coating (ARC) layer, and a photoresist layer. The metal-compound hard mask layer does not attenuate optical signals from lithographic alignment marks in underlying material layers, and can facilitate alignment between different levels in semiconductor manufacturing.Type: GrantFiled: January 15, 2013Date of Patent: March 24, 2015Assignee: International Business Machines CorporationInventors: Daniel C. Edelstein, Bryan G. Morris, Tuan A. Vo, Christopher J. Waskiewicz, Yunpeng Yin
-
Patent number: 8980524Abstract: A positive resist composition including a base component (A) which exhibits increased solubility in an alkali developing solution under action of acid, an acid-generator component (B) which generates acid upon exposure and a fluorine-containing polymeric compound (C?) which generates acid upon exposure, the base component (A) having a structural unit (a0-1) represented by general formula (a0-1) and a structural unit (a1) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group, and the fluorine-containing polymeric compound (C?) having a structural unit (c0) which generates acid upon exposure and a structural unit (c1) represented by formula (c1) (wherein R2 represents a divalent linking group, R3 represents a cyclic group containing —SO2— within the ring skeleton, Q0 represents a single bond or a divalent linking group, and R0 represents an organic group which may have a fluorine atom).Type: GrantFiled: December 27, 2010Date of Patent: March 17, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Tomoyuki Hirano, Daiju Shiono, Masatoshi Arai
-
Patent number: 8980527Abstract: A resist composition is provided comprising a polymer comprising recurring units having a carboxyl group substituted with an acid labile group, an acid generator, a sulfonium or iodonium salt of fluoroalkanesulfonamide and an organic solvent. A positive pattern is formed by applying the resist composition onto a substrate, prebaking to form a resist film, exposing the resist film to high-energy radiation, baking, and immersing in an alkaline developer to dissolve away the exposed region of resist film, but not the unexposed region.Type: GrantFiled: January 4, 2013Date of Patent: March 17, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Jun Hatakeyama
-
Publication number: 20150072292Abstract: Disclosed herein is a photoresist composition comprising a graft block copolymer; a solvent and a photoacid generator; where the graft block copolymer comprises a first block polymer; the first block polymer comprising a backbone polymer and a first graft polymer; where the first graft polymer comprises a surface energy reducing moiety that comprises a halocarbon moiety or a silicon containing moiety; and a second block polymer; the second block polymer being covalently bonded to the first block; wherein the second block comprises the backbone polymer and a second graft polymer; where the second graft polymer comprises a functional group that is operative to undergo deprotection and alter the solubility of the graft block copolymer; where the graft block copolymer has a bottle brush topology.Type: ApplicationFiled: September 6, 2013Publication date: March 12, 2015Inventors: Sangho Cho, Guorong Sun, Karen L. Wooley, James W. Thackeray, Peter Trefonas, III
-
Publication number: 20150072275Abstract: The present invention relates to a positive photosensitive resin composition and a method for forming a pattern by using the same. The positive photosensitive resin composition includes a novolac resin (A), a polysiloxane (B), an ortho-naphthoquinone diazide sulfonic acid ester (C) and a solvent (D). The novolac resin (A) includes a xylenol-type novolac resin (A-1). The xylenol-type novolac resin (A-1) is synthesized by polycondensing an aldehyde compound with a xylenol compound.Type: ApplicationFiled: September 3, 2014Publication date: March 12, 2015Inventors: Chi-Ming LIU, Chun-An SHIH
-
Patent number: 8975006Abstract: New photoresist compositions are provided that are useful for immersion lithography. Preferred photoresist compositions of the invention comprise one or more block copolymers. Particularly preferred photoresists of the invention can exhibit reduced leaching of resist materials into an immersion fluid contacting the resist layer dining immersion lithography processing.Type: GrantFiled: November 19, 2009Date of Patent: March 10, 2015Inventors: Deyan Wang, Charles R. Szmanda, George G. Barclay, Cheng-Bai Xu
-
Patent number: 8975002Abstract: A positive resist composition for immersion exposure includes the following (A) to (D): (A) a resin capable of decomposing by an action of an acid to increase a solubility of the resin in an alkali developer; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (C) a resin having at least either one of a fluorine atom and a silicon atom; and (D) a mixed solvent containing at least one kind of a solvent selected from the group consisting of solvents represented by any one of the following formulae (S1) to (S3) as defined in the specification, in which a total amount of the at least one kind of the solvent is from 3 to 20 mass % based on all solvents of the mixed solvent (D).Type: GrantFiled: August 15, 2013Date of Patent: March 10, 2015Assignee: FUJIFILM CorporationInventors: Kei Yamamoto, Hiroshi Saegusa
-
Publication number: 20150064626Abstract: A positive resist composition is provided comprising a polymer comprising recurring units having a carboxyl and/or phenolic hydroxyl group substituted with an acid labile group and recurring units of tert-butyl or tert-amyl-substituted hydroxyphenyl methacrylate and having a weight average molecular weight of 1,000-500,000. The resist composition has a satisfactory effect of suppressing acid diffusion and a high resolution, and forms a pattern of good profile and minimal edge roughness after exposure.Type: ApplicationFiled: July 14, 2014Publication date: March 5, 2015Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Koji Hasegawa
-
Patent number: 8968979Abstract: A positive resist composition comprises a polymer comprising repeat units having formula (1) or (2). Herein denotes an aromatic hydrocarbon group, R1 is H, methyl or trifluoromethyl, R2 is H, C1-C12 alkyl or aromatic hydrocarbon group, R3 is C1-C12 alkyl, or R2 and R3 may bond together to form a ring, and a is 1 or 2. When used in the ArF lithography, the resist composition exhibits high resolution. When used in the EB image writing for mask processing, the resist composition exhibits high resolution and sensitivity sufficient to comply with high-accelerating-voltage EB irradiation, and high etch resistance.Type: GrantFiled: November 20, 2009Date of Patent: March 3, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Katsuya Takemura, Keiichi Masunaga, Daisuke Domon, Masayoshi Sagehashi
-
Patent number: 8968982Abstract: In a chemically amplified positive resist composition comprising a base resin and an acid generator in a solvent, the base resin contains both an alkali-insoluble or substantially alkali-insoluble polymer having an acid labile group-protected acidic functional group having a Mw of 1,000-500,000 and an alkyl vinyl ether polymer having a Mw of 10,000-500,000. The composition forms on a substrate a resist film of 5-100 ?m thick which can be briefly developed to form a pattern at a high sensitivity and a high degree of removal or dissolution to bottom.Type: GrantFiled: January 19, 2012Date of Patent: March 3, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hiroyuki Yasuda, Katsuya Takemura
-
Publication number: 20150056557Abstract: A chemically amplified positive-type photosensitive resin composition including a compound represented by the following formula (1), having a melting point of 40° C. or lower at 1 atm, a resin whose solubility in alkali increases under the action of an acid, and a photoacid generator. In the formula, R1 represents a hydrogen atom or an organic group; and R2, R3, and R4 independently represent a monovalent hydrocarbon group which may have a substituent, and at least two of R2, R3, and R4 may be bonded to each other to form a cyclic structure.Type: ApplicationFiled: August 14, 2014Publication date: February 26, 2015Inventor: Makiko Irie
-
Patent number: 8962233Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes an arylsulfonium salt that when exposed to actinic rays or radiation, generates an acid, the arylsulfonium salt containing at least one aryl ring on which there are a total of one or more electron donating groups, the acid generated upon exposure to actinic rays or radiation having a volume of 240 ?3 or greater.Type: GrantFiled: January 28, 2011Date of Patent: February 24, 2015Assignee: FUJIFILM CorporationInventors: Takeshi Kawabata, Tomotaka Tsuchimura, Takayuki Ito
-
Patent number: 8956806Abstract: A method and material layer for forming a pattern are disclosed. The method includes providing a substrate; forming a first material layer over the substrate; forming a second material layer over the first material layer, wherein the second material layer comprises a photoacid generator and a photobase generator; and exposing one or more portions of the second material layer.Type: GrantFiled: September 18, 2009Date of Patent: February 17, 2015Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.Inventors: Chien-Wei Wang, Ching-Yu Chang, Burn Jeng Lin
-
Patent number: 8956803Abstract: The present invention provides a sulfonium salt used in a resist composition that can give a pattern having a high resolution, especially an excellent rectangularity of a pattern form and a small roughness, while not readily generating a defect, in the photolithography using a high energy beam as a light source; a resist composition that contains the sulfonium salt; and a patterning process using this resist composition, wherein the sulfonium salt is shown by the following general formula (1a), wherein each of R and R0 independently represents a hydrogen atom, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 30 carbon atoms which may be optionally substituted by a heteroatom or interposed by a heteroatom.Type: GrantFiled: December 6, 2013Date of Patent: February 17, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Tomohiro Kobayashi, Akihiro Seki, Masayoshi Sagehashi, Masahiro Fukushima
-
Patent number: 8956810Abstract: An undercoat agent usable in phase separation of a layer formed on a substrate, the layer containing a block copolymer having a plurality of polymers bonded, the undercoat agent including a resin component, and 20 mol % to 80 mol % of all the structural units of the resin component being a structural unit derived from an aromatic ring-containing monomer; and a method of forming a pattern of a layer containing a block copolymer, the method including: step (1) coating the undercoat agent on a substrate (1), thereby forming a layer (2) composed of the undercoat agent, step (2) forming a layer (3) containing a block copolymer having a plurality of polymers bonded on the surface of the layer (2) composed of the undercoat agent, and subjecting the layer (3) containing the block copolymer to phase separation, and step (3) selectively removing a phase (3a) of at least one polymer of the plurality of copolymers constituting the block copolymer from the layer (3) containing the block copolymer.Type: GrantFiled: September 12, 2011Date of Patent: February 17, 2015Assignees: Tokyo Ohka Kogyo Co., Ltd., RikenInventors: Takahiro Senzaki, Takahiro Dazai, Ken Miyagi, Shigenori Fujikawa, Harumi Hayakawa, Mari Koizumi
-
Patent number: 8956790Abstract: Disclosed is a positive photosensitive resin composition that includes (A) at least one dissolution controlling agent selected from a compound including a repeating unit represented by the following Chemical Formula 1, a compound including a repeating unit represented by the following Chemical Formula 2, or a combination thereof, (B) a polybenzoxazole precursor, (C) a photosensitive diazoquinone compound, and (D) a solvent. An organic insulator film for a display device manufactured using the same and a display device are also disclosed. In Chemical Formulae 1 and 2, each substituent is the same as defined in the detailed description.Type: GrantFiled: July 2, 2013Date of Patent: February 17, 2015Assignee: Cheil Industries Inc.Inventors: Jun-Ho Lee, Hyo-Young Kwon, Hwan-Sung Cheon
-
Patent number: 8956800Abstract: A method of forming a resist pattern, including: step (1) in which a resist composition containing a base component (A) that exhibits increased solubility in an alkali developing solution and a compound represented by general formula (C1) is applied to a substrate to form a resist film, step (2) in which the resist film is subjected to exposure, step (3) in which baking is conducted after step (2), and step (4) in which the resist film is subjected to an alkali development, thereby forming a negative-tone resist pattern; and the resist composition used in step (1): wherein R1 represents a group which forms an aromatic ring together with the two carbon atoms bonded to the R1 group; R2 represents a hydrogen atom or a hydrocarbon group; and R3 represents a hydrogen atom, a carboxy group or a hydrocarbon group of 1 to 15 carbon atoms.Type: GrantFiled: January 2, 2013Date of Patent: February 17, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroaki Shimizu, Jiro Yokoya, Tsuyoshi Nakamura, Hideto Nito
-
Publication number: 20150044616Abstract: A method of forming patterns includes (a) coating a substrate with a resist composition for negative development to form a resist film, wherein the resist composition contains a resin capable of increasing the polarity by the action of the acid and becomes more soluble in a positive developer and less soluble in a negative developer upon irradiation with an actinic ray or radiation, (b) forming a protective film on the resist film with a protective film composition after forming the resist film and before exposing the resist film, (c) exposing the resist film via an immersion medium, and (d) performing development with a negative developer.Type: ApplicationFiled: October 23, 2014Publication date: February 12, 2015Applicant: FUJIFILM CORPORATIONInventor: Hideaki TSUBAKI
-
Publication number: 20150044613Abstract: A chemically amplified photosensitive resin composition including a compound represented by formula (1) and/or formula (4), a resin having an acid-dissociative dissolution-controlling group whose solubility in alkali increases under the action of an acid or an alkali-soluble resin, a photoacid generator, and an organic solvent, in which the solid concentration is 40% by mass to 65% by mass. R1, R2, and R3 independently represent a hydrogen atom or an alkyl group, R4 represents a group represented by formula (2) or (3), and R5 and R6 represent a monovalent hydrocarbon group which may have a substituent.Type: ApplicationFiled: August 4, 2014Publication date: February 12, 2015Inventors: Makiko Irie, Shota Katayama
-
Patent number: 8951718Abstract: A pattern forming method, including: (A) coating a substrate with a positive resist composition of which solubility in a positive developer increases and solubility in a negative developer decreases upon irradiation with actinic rays or radiation, so as to form a resist film; (B) exposing the resist film; and (D) developing the resist film with a negative developer; a positive resist composition for multiple development used in the method; a developer for use in the method; and a rinsing solution for negative development used in the method.Type: GrantFiled: August 17, 2012Date of Patent: February 10, 2015Assignee: FUJIFILM CorporationInventors: Hideaki Tsubaki, Shinichi Kanna
-
Patent number: 8951712Abstract: A pattern is printed by forming a photoresist layer on a wafer, forming a protective film thereon, exposure, and development. The protective film is formed from a composition comprising a copolymer comprising recurring units derived from a styrene, indene, benzofuran or benzothiophene monomer having 1,1,1,3,3,3-hexafluoro-2-propanol, and recurring units derived from a styrene, vinylnaphthalene, indene, benzofuran, benzothiophene, stilbene, styrylnaphthalene or dinaphthylethylene monomer and an ether solvent.Type: GrantFiled: September 10, 2013Date of Patent: February 10, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Jun Hatakeyama
-
Patent number: 8945808Abstract: Resist compositions that can be used in immersion lithography without the use of an additional topcoat are disclosed. The resist compositions comprise a photoresist polymer, at least one photoacid generator, a solvent; and a self-topcoating resist additive. A method of forming a patterned material layer on a substrate using the resist composition is also disclosed.Type: GrantFiled: April 28, 2006Date of Patent: February 3, 2015Assignee: International Business Machines CorporationInventors: Robert Allen David, Phillip Joe Brock, Carl E Larson, Daniel Paul Sanders, Ratnam Sooriyakumaran, Linda Karin Sundberg, Hoa D Truong, Gregory Michael Wallraff
-
Patent number: 8945810Abstract: A positive resist composition comprises: (A) a resin that has a repeating unit represented by general formula (a1) and increases its solubility in an alkali developer by action of an acid; (B) a compound which generates an acid upon irradiation with an actinic ray or a radiation; and (C) a resin that has at least one of a fluorine atom and a silicon atom and has a group selected from the group consisting of (x), (y) and (z); and (D) a solvent: (x) an alkali-soluble group; (y) a group capable that decomposes by action of an alkali developer to undergo an increase in a solubility of the resin (C) in an alkali developer; and (z) a group that decomposes by action of an acid, wherein R represents a hydrogen atom or a methyl group, Rxa represents an alkyl group or a cycloalkyl group, and n represents an integer of 1 to 8.Type: GrantFiled: June 30, 2011Date of Patent: February 3, 2015Assignee: FUJIFILM CorporationInventors: Fumiyuki Nishiyama, Hiromi Kanda
-
Patent number: 8940470Abstract: A material for a microlens having heat resistance, high resolution and high light-extraction efficiency is provided. A positive resist composition comprises an alkali-soluble polymer containing a unit structure having an aromatic fused ring or a derivative thereof, and a compound having an organic group which undergoes photodecomposition to yield an alkali-soluble group. The positive resist composition has coating film properties of a refractive index at a wavelength of 633 nm of 1.6 or more and a transmittance at wavelengths of 400 to 730 nm of 80% or more. A pattern forming method comprises applying the positive resist composition, drying the composition, exposing the composition to light, and developing the composition.Type: GrantFiled: May 14, 2008Date of Patent: January 27, 2015Assignee: Nissan Chemical Industries, Inc.Inventors: Takayuki Negi, Takahiro Sakaguchi, Takahiro Kishioka
-
Patent number: 8940473Abstract: A resist composition contains (A1) a resin having a structural unit represented by the formula (I), (A2) a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid, and (B) an acid generator represented by the formula (II). wherein R1 represents a hydrogen atom or a methyl group; A1 represents a C1 to C6 alkanediyl group; R2 represents a C1 to C10 hydrocarbon group having a fluorine atom; R3 and R4 independently represent a fluorine atom or a C1 to C6 perfluoroalkyl group; X1 represents an C1 to C17 divalent saturated hydrocarbon group; R5 represents a group having cyclic ether structure; and Z1+ represents an organic cation.Type: GrantFiled: February 24, 2012Date of Patent: January 27, 2015Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Yuichi Mukai, Satoshi Yamamoto
-
Patent number: 8940472Abstract: Organic coating compositions, particularly antireflective coating compositions, are provided that comprise that comprise a diene/dienophile reaction product. Preferred compositions of the invention are useful to reduce reflection of exposing radiation from a substrate back into an overcoated photoresist layer and/or function as a planarizing, conformal or via-fill layer.Type: GrantFiled: February 8, 2010Date of Patent: January 27, 2015Inventors: James F. Cameron, Jin Wuk Sung, John P. Amara, Greogory P. Prokopowicz, David A. Valeri
-
Patent number: 8936900Abstract: A molecular glass compound comprises a vinyl ether adduct of an aromatic vinyl ether of formula C(R1)2?C(R2)—O-(L)n-Ar1, and a calix[4]arene, wherein R1 and R2 are each independently a single bond, H, C1-20 alkyl, C1-20 haloalkyl, C6-20 aryl, C6-20 haloaryl, C7-20 aralkyl, or C7-20 haloaralkyl, L is a C1-20 linking group, n is 0 or 1, and Ar1 is a halo-containing monocyclic, or substituted or unsubstituted polycyclic or fused polycyclic C6-20 aromatic-containing moiety, wherein R1 and R2 are connected to Ar1 when either or both of R1 and R2 is a single bond and n is 0. A photoresist, comprising the molecular glass compound, a solvent, and a photoacid generator, a coated substrate, comprising (a) a substrate having one or more layers to be patterned on a surface thereof; and (b) a layer of a photoresist composition over the one or more layers to be patterned, and a method of forming the molecular glass compound, are also disclosed.Type: GrantFiled: September 21, 2012Date of Patent: January 20, 2015Assignees: Rohm and Haas Electronic Materials LLC, Dow Global Technologies LLCInventors: Vipul Jain, D. Patrick Green, James W. Thackeray, Brad C. Bailey, Su Jin Kang
-
Publication number: 20150017576Abstract: There is provided a pattern forming method comprising, in order: (i) a step of forming a film by using an extreme ultraviolet-sensitive resin composition containing (A) a resin having an acid-decomposable group; (ii) a step of exposing the film by using an extreme ultraviolet ray; (iii) a step of heating the film; and (iv) a step of developing the film to form a pattern, wherein in the step (ii), an optical image formed by exposure on the surface of the film is an optical image having a line part with a line width of 20 nm or less as an exposed area or an unexposed area, and, the heating temperature TPEB(° C.) in the step (iii) satisfies the specific formula.Type: ApplicationFiled: September 29, 2014Publication date: January 15, 2015Applicant: FUJIFILM CORPORATIONInventors: Naoki INOUE, Hiroo TAKIZAWA, Hideaki TSUBAKI
-
Publication number: 20150017586Abstract: A positive resist composition is provided comprising a polymer comprising recurring units having a carboxyl or phenolic hydroxyl group substituted with an acid labile group and recurring units of hydroxyanthraquinone or hydroxy-2,3-dihydro-1,4-anthracenedione methacrylate, and having a Mw of 1,000-500,000. The resist composition has a satisfactory effect of suppressing acid diffusion and a high resolution, and forms a pattern of good profile and minimal edge roughness after exposure.Type: ApplicationFiled: July 3, 2014Publication date: January 15, 2015Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Masayoshi Sagehashi
-
Patent number: 8932797Abstract: A photoacid generator compound has formula (I): G+Z???(I) wherein G has formula (II): In formula (II), X is S or I, each R0 is commonly attached to X and is independently C1-30 alkyl; polycyclic or monocyclic C3-30 cycloalkyl; polycyclic or monocyclic C6-30 aryl; or a combination comprising at least one of the foregoing groups. G has a molecular weight greater than 263.4 g/mol, or less than 263.4 g/mol. One or more R0 groups are further attached to an adjacent R0 group, a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 2 or 3. Z in formula (I) comprises the anion of a sulfonic acid, a sulfonimide, or a sulfonamide. A photoresist and coated film also includes the photoacid generator, and a method of forming an electronic device uses the photoresist.Type: GrantFiled: November 30, 2011Date of Patent: January 13, 2015Assignees: Dow Global Technologies LLC, Rohm and Haas Electronic Materials LLCInventors: James W. Thackeray, Suzanne M. Coley, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour, Owendi Ongayi, Vipul Jain
-
Patent number: 8932794Abstract: A positive photosensitive composition, includes: (A) a resin having a repeating unit represented by formula (1) as defined in the specification and a repeating unit represented by formula (2) as defined in the specification and being capable of increasing a solubility of the resin (A) in an alkali developer by an action of an acid; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; and a solvent, and a pattern forming method uses the positive photosensitive composition.Type: GrantFiled: September 29, 2009Date of Patent: January 13, 2015Assignee: FUJIFILM CorporationInventors: Toshiaki Fukuhara, Akinori Shibuya, Takayuki Kato
-
Patent number: 8932800Abstract: The present invention provides a positive photosensitive resin composition including: a resin containing a specific acrylic acid-based constituent unit capable of undergoing dissociation of an acid-dissociable group to produce a carboxyl group, and a constituent unit having a functional group capable of reacting with the carboxyl group to form a covalent bond, the resin being alkali-insoluble or sparingly alkali-soluble and becoming alkali-soluble when the acid-dissociable group dissociates; and a compound capable of generating an acid upon irradiation with an actinic ray or radiation. The present invention also provides a method for forming a cured film using the composition. The positive photosensitive composition is excellent in the sensitivity, film residual ratio and storage stability and by the method for forming a cured film using the positive photosensitive resin composition, a cured film excellent in the heat resistance, adhesion, transmittance and the like can be provided.Type: GrantFiled: November 12, 2012Date of Patent: January 13, 2015Assignee: FUJIFILM CorporationInventor: Satoshi Takita
-
Patent number: 8921028Abstract: A salt represented by the formula (I) and a resist composition containing the salt are provided, wherein Q1, Q2, L1, ring W1, Re1, Re2, Re3, Re4, Re5, Re6, Re7, Re8, Re9, Re10, Re11, Re12, Re13 and Z are defined in the specification.Type: GrantFiled: March 7, 2012Date of Patent: December 30, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Koji Ichikawa
-
Patent number: 8921029Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, R2, RII1, RII2, LII1, YII1, RII3, RII4, RII5, RII6, RII7, n, s and RII8 are defined in the specification.Type: GrantFiled: July 18, 2012Date of Patent: December 30, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
-
Publication number: 20140377708Abstract: A method of manufacturing using a double patterning method is provided. The double patterning method uses a first developer and a second developer that are different. For example, the first developer may be a positive tone developer for a positive photoresist while the second developer may be a negative tone developer for the positive photoresist. Photoresists having a photoactive compound are also provided that may be useful in double patterning methods. The resulting double patterning results, wherein a dimension of a variable first dense pattern is larger than a dimension of a variable second dense pattern.Type: ApplicationFiled: September 12, 2014Publication date: December 25, 2014Inventor: Chin Cheng Yang
-
Publication number: 20140377706Abstract: An aqueous solution containing 0.1-20 wt % of a substituted choline or thiocholine hydroxide is a useful developer for photosensitive resist materials. A resist pattern is formed by applying a chemically amplified positive resist composition onto a substrate to form a resist film, exposing the resist film to high-energy radiation, and developing the exposed resist film in an ammonium hydroxide-containing aqueous solution.Type: ApplicationFiled: May 27, 2014Publication date: December 25, 2014Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Masaki Ohashi
-
Patent number: 8916330Abstract: The present invention provides a resist composition giving a resist pattern excellent in CD uniformity and focus margin. A chemically amplified photoresist composition comprises a resin (A) and an acid generator (B), and the resin (A) contains, as a part or an entirety thereof, a copolymer (A1) which is obtained by polymerizing at least: a (meth)acrylic monomer (a1) having C5-20 alicyclic hydrocarbon group which becomes soluble in an aqueous alkali solution by the action of an acid; a (meth)acrylic monomer (a2) having a hydroxy group-containing adamantyl group; and a (meth)acrylic monomer (a3) having a lactone ring, and the copolymer (A1) has a weight-average molecular weight of 2500 or more and 5000 or less, and a content of the copolymer (A1) is not less than 50 parts by mass with respect to 100 parts by mass of the resin (A).Type: GrantFiled: June 23, 2010Date of Patent: December 23, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Takashi Hiraoka
-
Patent number: 8916327Abstract: There is provided an underlayer coating forming composition for lithography, and an underlayer coating having a high dry etching rate compared with photoresist, and causing no intermixing with the photoresist, which are used in lithography process of manufacture of semiconductor device. Concretely, it is an underlayer coating forming composition for lithography comprising a dextrin ester compound that at least 50% of hydroxy groups in dextrin is converted into ester groups, a crosslinking compound, and an organic solvent.Type: GrantFiled: October 29, 2004Date of Patent: December 23, 2014Assignee: Nissan Chemical Industries, Ltd.Inventors: Satoshi Takei, Yasushi Sakaida, Tetsuya Shinjo
-
Publication number: 20140370441Abstract: An aqueous solution containing 0.1-20 wt % of a cyclic ammonium hydroxide is a useful developer for photosensitive resist materials. A resist pattern is formed by applying a chemically amplified positive resist composition onto a substrate to form a resist film, exposing the resist film to high-energy radiation, and developing the exposed resist film in a cyclic ammonium hydroxide-containing aqueous solution.Type: ApplicationFiled: May 27, 2014Publication date: December 18, 2014Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Masaki Ohashi
-
Patent number: 8911932Abstract: Disclosed are the deactivation mechanism and chemistry platforms that make high-silicon hardmask films photo-imageable like positive-tone photoresist for microphotolithography. The deactivation mechanism requires a catalyst to promote crosslinking reactions, and a photoacid generator to deactivate the catalyst. The initial hardmask films are soluble in developers. If not radiated, films become insoluble in developers due to crosslinking reactions promoted by catalyst. If radiated, films remain soluble in developers due to deactivation of catalyst by photoacid generator. Compositions of positive-tone photo-imageable hardmask based on the chemistry of polysiloxane and polysilsesquioxanes are disclosed as well. Also disclosed is a method of modifying polysiloxane and polysilsesquioxane films for controlled diffusion of catalysts, photoacid generators, and quenchers.Type: GrantFiled: April 12, 2010Date of Patent: December 16, 2014Inventor: Sam Xunyun Sun
-
Patent number: 8911929Abstract: An aqueous solution containing 0.1-10 wt % of a guanidine is a useful developer for photosensitive resist materials. A resist pattern is formed by applying a chemically amplified positive resist composition onto a substrate to form a coating, baking, exposing the coating to high-energy radiation, and developing the exposed coating in a guanidine-containing aqueous solution.Type: GrantFiled: November 20, 2013Date of Patent: December 16, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Jun Hatakeyama
-
Patent number: 8911928Abstract: A resist composition including a base component (A) that exhibits changed solubility in a developing solution under action of acid and an acid generator component (B) that generates acid upon exposure, wherein the base component (A) contains a resin component (A1) including a structural unit (a0) represented by general formula (a0-1) shown below and a structural unit (a1)) containing an acid decomposable group that exhibits increased polarity under action of acid, and the amount of the structural unit (a0) is less than 50 mol %, wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; R1 represents a divalent linking group; R2 represents a —SO2— containing cyclic group; and v represents 0 or 1.Type: GrantFiled: May 22, 2012Date of Patent: December 16, 2014Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Tomoyuki Hirano, Daiju Shiono, Daichi Takaki, Junichi Tsuchiya
-
Patent number: 8906802Abstract: One illustrative method disclosed herein includes the steps of performing a directed self-assembly process to form a DSA masking layer, performing at least one process operation to remove at least one of the features of the DSA masking layer so as to thereby define a patterned DSA masking layer with a DSA masking pattern, performing at least one process operation to form a patterned transfer masking layer having a transfer masking pattern comprised of a plurality of features that define a plurality of openings in the transfer masking layer, wherein the transfer masking pattern is the inverse of the DSA masking pattern, and performing at least one etching process through the patterned transfer masking layer on a layer of material to form a plurality of trench/via features in the layer of material.Type: GrantFiled: March 15, 2013Date of Patent: December 9, 2014Assignee: GLOBALFOUNDRIES Inc.Inventors: Jeremy A. Wahl, Gerard M. Schmid, Richard A. Farrell, Chanro Park
-
Patent number: 8900790Abstract: A photoresist composition comprising a resin, an acid generator and a compound represented by the formula (I): wherein R1 represents a C2-C12 alkyl group which can have one or more hydroxyl groups, etc., R2 and R3 each independently represent a hydrogen atom, etc., R4, R5 and R6 each independently represent a hydrogen atom, etc., A1 represents a single bond or a C1-C2 alkylene group in which one or more —CH2— can be replaced by —O—.Type: GrantFiled: September 13, 2010Date of Patent: December 2, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuro Masuyama, Mitsuhiro Hata
-
Patent number: 8900793Abstract: There is disclosed a polymer having a repeating unit shown by the following general formula (1). There can be, in a photolithography using a high energy beam such as an ArF excimer laser beam and an EUV as a light source, (1) a polymer that gives a resist composition having an appropriate adhesion with a substrate and being capable of forming a pattern having excellent resolution, especially an excellent rectangular pattern profile, (2) a chemically amplified resist composition containing the said polymer, and (3) a patterning process using the said chemically amplified resist composition.Type: GrantFiled: May 21, 2012Date of Patent: December 2, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayoshi Sagehashi, Youichi Ohsawa, Koji Hasegawa, Tomohiro Kobayashi
-
Patent number: 8900802Abstract: Provided is a method for developing positive-tone chemically amplified resists with an organic developer solvent having at least one polyhydric alcohol, such as ethylene glycol and/or glycerol, alone or in combination with an additional organic solvent, such as isopropyl alcohol, and/or water. The organic solvent developed positive tone resists described herein are useful for lithography pattern forming processes; for producing semiconductor devices, such as integrated circuits (IC); and for applications where basic solvents are not suitable, such as the fabrication of chips patterned with arrays of biomolecules or deprotection applications that do not require the presence of acid moieties.Type: GrantFiled: February 23, 2013Date of Patent: December 2, 2014Assignees: International Business Machines Corporation, JSR CorporationInventors: Robert D. Allen, Ramakrishnan Ayothi, Luisa D. Bozano, William D. Hinsberg, Linda K. Sundberg, Sally A. Swanson, Hoa D. Truong, Gregory M. Wallraff
-
Patent number: 8900792Abstract: A compound has formula (I): Q-O-(A)-Z?G+??(I) wherein Q is a halogenated or non-halogenated, C2-30 olefin-containing group, A is a fluorine-substituted C1-30 alkylene group, a fluorine-substituted C3-30 cycloalkylene group, a fluorine-substituted C6-30 arylene group, or a fluorine-substituted C7-30 alkylene-arylene group, Z is an anionic group comprising sulfonate, sulfonamide, or sulfonimide, and G+ has formula (II): wherein X is S or I, each R0 is halogenated or non-halogenated and is independently C1-30 alkyl group; a polycyclic or monocyclic C3-30 cycloalkyl group; a polycyclic or monocyclic C4-30 aryl group; or a combination of these, wherein when X is S, one of the R0 groups is optionally attached to one adjacent R0 group by a single bond, and a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 3. A copolymer, a photoresist, a coated substrate and method of patterning are disclosed.Type: GrantFiled: December 29, 2011Date of Patent: December 2, 2014Assignees: Rohm and Haas Electronic Materials LLC, Dow Global Technologies LLCInventors: James W. Thackeray, Suzanne M. Coley, Vipul Jain, Owendi Ongayi, James F. Cameron, Paul J. Labeaume, Ahmad E. Madkour