Halogen Compound Containing Patents (Class 430/925)
  • Patent number: 7547501
    Abstract: The present application relates to photoactive materials having the formula wherein C1+ is a cation; each of R30, R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, and R41 are selected from hydrogen, alkyl, alkyl chain optionally containing one or more O atoms, halide, aryl, aralkyl, alkoxyalkyl, cycloalkyl, hydroxyl, and alkoxy, the alkyl, alkyl chain optionally containing one or more O atoms, aryl, aralkyl, alkoxyalkyl, cycloalkyl, and alkoxy groups being unsubstituted or substituted.
    Type: Grant
    Filed: October 5, 2006
    Date of Patent: June 16, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Ralph R. Dammel, M. Dalil Rahman, David L. Rentkiewicz, Karl van Werden
  • Patent number: 7531290
    Abstract: Sulfonate salts have the formula: R1SO3—CH(Rf)—CF2SO3?M+ wherein R1 is alkyl or aryl, Rf is H or trifluoromethyl, and M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: October 27, 2006
    Date of Patent: May 12, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
  • 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: 7527912
    Abstract: Photoacid generators generate sulfonic acids of formula (1a) upon exposure to high-energy radiation. RC(?O)R1—COOCH(CF3)CF2SO3?H+??(1a) R is hydroxyl, alkyl, aryl, hetero-aryl, alkoxy, aryloxy or hetero-aryloxy, R1 is a divalent organic group which may have a heteroatom (O, N or S) containing substituent, or R1 may form a cyclic structure with R. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.
    Type: Grant
    Filed: September 27, 2007
    Date of Patent: May 5, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Koji Hasegawa, Masaki Ohashi
  • Patent number: 7524614
    Abstract: A radiation-sensitive composition includes a radically polymerizable component and an iodonium borate initiator composition capable of generating radicals sufficient to initiate polymerization of the free radically polymerizable component upon exposure to imaging radiation. The iodonium borate composition includes a particular diaryliodonium borate compound having organic substituents to provide a sum of at least 6 carbon atoms on the iodonium cation phenyl rings. This composition can be applied to a suitable substrate to provide a negative-working imageable element with improved digital speed and good shelf life and that can be imaged to provide lithographic printing plates. The imaged elements can be developed either on-press or off-press using alkaline developers.
    Type: Grant
    Filed: May 26, 2006
    Date of Patent: April 28, 2009
    Assignee: Eastman Kodak Company
    Inventors: Ting Tao, Scott A. Beckley
  • 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: 7514202
    Abstract: A thermal acid generator of generating an acid on heating above 100° C. has formula: CF3CH(OCOR)CF2SO3?(R1)4N+ wherein R is alkyl or aryl, R1 is hydrogen, alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl, or R1 may bond together to form a ring with N. The sulfonic acid generated possesses an ester site within molecule so that less bulky acyl groups to bulky groups may be incorporated therein. The thermal acid generator provides a sufficient acid strength, is less volatile due to a high molecular weight, and ensures film formation. Upon disposal of used resist liquid, it may be converted into low accumulative compounds.
    Type: Grant
    Filed: May 9, 2007
    Date of Patent: April 7, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Jun Hatakeyama
  • Patent number: 7510816
    Abstract: A resist composition is provided comprising a polysiloxane, a specific acid generator, a nitrogen-containing organic compound, and a solvent. The resist composition exerts high-resolution performance without the problem of a T-top profile and is suited for the bilayer resist process using ArF exposure.
    Type: Grant
    Filed: October 4, 2005
    Date of Patent: March 31, 2009
    Assignee: Shin-Estu Chemical Co., Ltd.
    Inventors: Katsuya Takemura, Kazumi Noda, Youichi Ohsawa
  • Patent number: 7511169
    Abstract: Sulfonate salts have the formula: CF3—CH(OCOR)—CF2SO3?M+ wherein R is C1-C20 alkyl or C6-C14 aryl, and M+ is a lithium, sodium, potassium, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: April 5, 2006
    Date of Patent: March 31, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
  • Patent number: 7501222
    Abstract: A polymer including a monomer represented by the following Formula and a photoresist composition including the same are disclosed. The polymer and photoresist composition can improve the resolution and the process margin due to the low activation energy of the deprotection reaction of the alcohol ester group including saturated cyclic hydrocarbyl group, and also can produce fine photoresist patterns because they have a stable PEB(Post Exposure Baking) temperature sensitivity, and further, can improve the focus depth margin and the line edge roughness of the resist layer. In the above Formula, R* is a hydrogen or methyl group, R1 is saturated hydrocarbyl group of 1 to 5 carbon atoms, R is mono-cyclic or multi-cyclic homo or hetero saturated hydrocarbyl group of 3 to 50 carbon atoms, and n is an integer of at least 2.
    Type: Grant
    Filed: June 21, 2006
    Date of Patent: March 10, 2009
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jung-Youl Lee, Jae-Woo Lee, Jae-Hyun Kim
  • Patent number: 7491482
    Abstract: The present application relates to a compound of formula AiXi where Ai is an organic onium cation; and Xi is an anion of the formula X—CF2CF2OCF2CF2—SO3?. The compounds are useful as photoactive materials.
    Type: Grant
    Filed: December 4, 2006
    Date of Patent: February 17, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Munirathna Padmanaban, Srinivasan Chakrapani, M. Dalil Rahman
  • Patent number: 7485407
    Abstract: Disclosed are a siloxane compound, a photoresist composition using the same, and a method of forming a pattern, wherein the siloxane compound is having a general formula: wherein R1 is a tertiary butyl group or a 1-(tert-butoxy)ethyl group, and R2 and R3 is each independently a lower alkyl group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: December 18, 2006
    Date of Patent: February 3, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim, Do-Young Kim
  • Patent number: 7482107
    Abstract: Photoresist compositions having a resin binder with an acid labile blocking group with an activation energy in excess of 20 Kcal/mol. for deblocking, a photoacid generator capable of generating a halogenated sulfonic acid upon photolysis and optionally, a base.
    Type: Grant
    Filed: March 23, 2006
    Date of Patent: January 27, 2009
    Assignee: Shipley Company, L.L.C.
    Inventors: James W. Thackeray, James F. Cameron, Roger F. Sinta
  • Patent number: 7482111
    Abstract: It is an object of the present invention to provide a process capable of precisely producing a plated shaped article of a large thickness such as a bump or a wiring, a negative radiation-sensitive resin composition which is preferably used for the process and has excellent sensitivity and resolution, and a transfer film using the composition. The above object is achieved by a negative radiation-sensitive resin composition comprising (A) a polymer containing structural units represented by the following formula (1) and/or the following formula (2), (B) a compound having at least one ethylenically unsaturated double bond and (C) a radiation-sensitive radical polymerization initiator, and by forming a negative radiation-sensitive resin film using the composition.
    Type: Grant
    Filed: March 24, 2005
    Date of Patent: January 27, 2009
    Assignee: JSR Corporation
    Inventors: Kouji Nishikawa, Tooru Kimura, Shin-ichiro Iwanaga
  • Patent number: 7459261
    Abstract: There is disclosed a resist composition which comprises, at least, a polymer in which a sulfonium salt having a polymerizable unsaturated bond, a (meth)acrylate having a lactone or a hydroxyl group as an adhesion group, and a (meth)acrylate having an ester substituted with an acid labile group are copolymerized. There can be provided a resist composition with high resolution which has high sensitivity and high resolution to high energy beam, especially to ArF excimer laser, F2 excimer laser, EUV, X-ray, EB, etc., has reduced line edge roughness, and comprises a polymeric acid generator which has insolubility in water, and sufficient thermal stability and preservation stability.
    Type: Grant
    Filed: December 19, 2005
    Date of Patent: December 2, 2008
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Youichi Ohsawa, Seiichiro Tachibana
  • Patent number: 7422839
    Abstract: The use of a positive resist composition that includes a resin with a specific structure improves the resolution and yields a resist pattern with a favorable shape. In addition, when a resist layer is formed on either a magnetic film or a metallic oxidation prevention film formed on the magnetic film, the layer is less prone to tailing and undercutting phenomena.
    Type: Grant
    Filed: July 5, 2004
    Date of Patent: September 9, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Hiroshi Shimbori
  • Patent number: 7419760
    Abstract: Disclosed herein is a top anti-reflective coating composition comprising a bissulfone compound, as a photoacid generator, represented by Formula 1 below: wherein R1 and R2 are independently, a straight, branched or cyclic alkyl, aryl, alkenyl, oxoalkyl or oxoaryl group of 1 to 20 carbon atoms; or a halogen-substituted straight, branched or cyclic alkyl, aryl, alkenyl, oxoalkyl or oxoaryl group of 1 to 20 carbon atoms. Since the top anti-reflective coating composition dissolves a portion of a photoacid generator present at the top of an underlying photosensitizer, particularly, upon formation of a top anti-reflective coating, it can prevent the top from being formed into a thick section. Therefore, the use of the anti-reflective coating composition enables the formation of a vertical pattern of a semiconductor device.
    Type: Grant
    Filed: June 22, 2005
    Date of Patent: September 2, 2008
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Cheol Kyu Bok, Sam Young Kim, Chang Moon Lim, Seung Chan Moon
  • Patent number: 7393627
    Abstract: Novel classes of ionic photoacid generator (PAGs) compounds having relatively environmentally friendly anions with no perfluorooctyl sulfonate (no-PFOS) are provided and photoresist composition that comprise such compounds. The new PAGs produce a photoacid having a short or no perfluoro alkyl chain (ie., no-PFOS) attached to a variety of functional groups. The PAGs of the invention are useful as photoactive component in the chemically amplified resist compositions used for microfabrication.
    Type: Grant
    Filed: March 16, 2005
    Date of Patent: July 1, 2008
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Ramakrishnan Ayothi, Kyung-Min Kim, Xiang-Qian Liu
  • Patent number: 7368224
    Abstract: The invention provides a photopolymerizable composition having a high photosensitivity, which comprises a metal complex of a squarylium compound, a radical generator, and a compound having at least one ethylenically unsaturated double bond. The photopolymerizable composition of the present invention is advantageously used for a visible laser recording material such as a PS (Presensitized Plate) for laser direct plate-making, a dry film resist, a digital proof, a hologram, or the like, a panchromatic sensitive material (e.g., a sensitive material for a color hologram and a sensitive material used for full-color display and containing a photopolymerizable composition in a microcapsule), paints, adhesives, and so on.
    Type: Grant
    Filed: April 3, 2003
    Date of Patent: May 6, 2008
    Assignee: Kyowa Hakko Chemical Co., Ltd.
    Inventors: Tsuguo Yamaoka, Ikuo Shimizu, Hiroshi Toyoda, Motoharu Kinugasa, Masanori Ikuta, Kyoko Katagi
  • Patent number: 7351515
    Abstract: A positive resist composition includes: (A) a resin capable of increasing a solubility thereof in an alkali developer by an action of an acid; (B) a compound capable of generating a sulfonic acid represented by the following formula (I) upon irradiation with one of an actinic ray and a radiation; and (C1) at least one of an amine compound having at least an aliphatic hydroxyl group in a molecule and an amine compound having at least an ether bond in a molecule: A1A2-SO3H)n ??(I) wherein A1 represents an n-valent linking group, A2 represents a single bond or a divalent aliphatic group, and A2's each may be the same or different, provided that at least one group represented by A1 or A2 contains a fluorine atom, and n represents an integer of from 2 to 4.
    Type: Grant
    Filed: September 16, 2004
    Date of Patent: April 1, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Shoichiro Yasunami, Kenji Wada, Kunihiko Kodama, Kenichiro Sato
  • Patent number: 7303855
    Abstract: An undercoat-forming material comprising a novolak resin having a fluorene or tetrahydrospirobiindene structure, an organic solvent, an acid generator, and a crosslinker, optionally combined with an intermediate layer having an antireflective effect, has an absorptivity coefficient sufficient to provide an antireflective effect at a thickness of at least 200 nm and a high etching resistance as demonstrated by slow etching rates with CF4/CHF3 and Cl2. BCl3 gases for substrate processing.
    Type: Grant
    Filed: September 30, 2004
    Date of Patent: December 4, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Satoshi Watanabe
  • Patent number: 7288359
    Abstract: A radiation-sensitive resin composition comprising (A) an acid-dissociable group-containing polysiloxane and (B) a photoacid generator containing trifluoromethane sulfonic acid or a compound which generates an acid of the following formula (I), wherein Rf individually represents a fluorine atom or a trifluoromethyl group, and Ra represents a hydrogen atom, a fluorine atom, a linear or branched alkyl group having 1-20 carbon atoms, or a linear or branched fluoroalkyl group having 1-20 carbon atoms, a substituted or unsubstituted monovalent cyclic hydrocarbon group having 3-20 carbon atoms, or a substituted or unsubstituted monovalent cyclic fluoro-hydrocarbon group having 3-20 carbon atoms. The radiation-sensitive resin composition of the present invention exhibits superior resolution, while maintaining high transparency to radiations and high dry etching resistance. The resin composition thus can greatly contribute to the lithography process that will become more and more minute in the future.
    Type: Grant
    Filed: December 4, 2002
    Date of Patent: October 30, 2007
    Assignee: JSR Corporation
    Inventors: Haruo Iwasawa, Akihiro Hayashi, Tsutomu Shimokawa
  • Patent number: 7285369
    Abstract: A positive resist composition comprising (A) a resin that increases solubility in an alkali developing solution by the action of an acid and (B-1) a compound having a structure represented by formula (I) defined in the specification.
    Type: Grant
    Filed: September 17, 2004
    Date of Patent: October 23, 2007
    Assignee: FUJIFILM Corporation
    Inventor: Hyou Takahashi
  • Patent number: 7270936
    Abstract: A negative resist composition and a method for patterning semiconductor devices using the composition are provided. The negative resist composition contains an alkali-soluble hydroxy-substituted base polymer, a silicon-containing crosslinker having an epoxy ring, and a photoacid generator. In the method for patterning semiconductor devices, fine patterns are formed according to a bi-layer resist process using the negative resist composition.
    Type: Grant
    Filed: July 6, 2005
    Date of Patent: September 18, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventor: Sang-Jun Choi
  • Patent number: 7235344
    Abstract: A composition including a first moiety; and a different second moiety capable of harvesting energy from an external source, wherein the second moiety is positioned such that energy harvested at the second moiety may be transferred to the first moiety. An article of manufacture including a film including a first moiety and a different second moiety capable of harvesting energy from an external source, wherein the second moiety is positioned such that collectively the first and second moieties have an electron capture cross-section greater than the electron capture cross-section of the first moiety alone. A method including forming a film on a substrate including a first moiety and a different second moiety; exposing the film to photonic or charged particle radiation; and patterning the film.
    Type: Grant
    Filed: June 30, 2004
    Date of Patent: June 26, 2007
    Assignee: Intel Corporation
    Inventors: Robert P. Meagley, Michael D. Goodner, Robert E. Leet, Michael L. McSwiney
  • Patent number: 7232647
    Abstract: The present invention provides a photosensitive resin composition for laser scanning exposure, which satisfies the following formula (1): - 25 ? E 1 - E 0 E 0 × 100 ? 25 ( 1 ) wherein E0 represents an exposure amount in mJ/cm2 at which the photosensitive resin composition is cured at the 21st step of the density 1.00 of a 41-step step tablet having a density range from 0.00 to 2.00, a density step of 0.05, a tablet size of 20 mm×187 mm and a step size of 3 mm×12 mm, by irradiation with a full wavelength active light of a high pressure mercury lamp and E1 represents an exposure amount in mJ/cm2 at which the photosensitive resin composition after being left for 2 hours under 40 W non-ultraviolet white lamp is cured at the 21st step of the 41-step step tablet by irradiation with a full wavelength active light from a high pressure mercury lamp.
    Type: Grant
    Filed: March 21, 2005
    Date of Patent: June 19, 2007
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Yasuhara Murakami, Takahiro Hidaka
  • 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: 7220533
    Abstract: The present invention provides a photosensitive resin composition for laser scanning exposure, which satisfies the following formula (1): - 25 ? E 1 - E 0 E 0 × 100 ? 25 ( 1 ) wherein E0 represents an exposure amount in mJ/cm2 at which the photosensitive resin composition is cured at the 21st step of the density 1.00 of a 41-step step tablet having a density range from 0.00 to 2.00, a density step of 0.05, a tablet size of 20 mm×187 mm and a step size of 3 mm×12 mm, by irradiation with a full wavelength active light of a high pressure mercury lamp and E1 represents an exposure amount in mJ/cm2 at which the photosensitive resin composition after being left for 2 hours under 40 W non-ultraviolet white lamp is cured at the 21st step of the 41-step step tablet by irradiation with a full wavelength active light from a high pressure mercury lamp.
    Type: Grant
    Filed: March 21, 2001
    Date of Patent: May 22, 2007
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Yasuharu Murakami, Takahiro Hidaka
  • Patent number: 7217496
    Abstract: A photoresist composition including a polymer is disclosed, wherein the polymer includes at least one monomer having the formula: where R1 represents hydrogen (H), a linear, branched or cyclo alkyl group of 1 to 20 carbons, a semi- or perfluorinated linear, branched or cyclo alkyl group of 1 to 20 carbons or CN; R2 represents an alicyclic group of 5 or more carbon atoms; X represents a methylene, ether, ester, amide or carbonate linkage; R3 represents a linear or branched alkylene group or semi- or perfluorinated linear or branched alkylene group with 1 or more carbon atoms; R4 represents hydrogen (H), methyl (CH3), trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perflourinated aliphatic group; R5 represents trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated substituted or unsubstituted aliphatic group; n represents an integer of 1 or more; and OR12 represents OH or at least one acid labile group selected from a tertiary alkyl c
    Type: Grant
    Filed: November 12, 2004
    Date of Patent: May 15, 2007
    Assignee: International Business Machines Corporation
    Inventors: Mahmoud Khojasteh, Pushkara Rao Varanasi, Wenjie Li, Kuang-Jung J Chen, Kaushal S. Patel
  • Patent number: 7208260
    Abstract: The present invention discloses a cross-linking monomer represented by the following Chemical Formula 1, a process for preparing a photoresist polymer using the same, and said photoresist polymer: <Chemical Formula> wherein, R? and R? individually represent hydrogen or methyl; m represents a number of 1 to 10; and R is selected from the group consisting of straight or branched C1-10 alkyl, straight or branched C1-10 ester, straight or branched C1-10 ketone, straight or branched C1-10 carboxylic acid, straight or branched C1-10 acetal, straight or branched C1-10 alkyl including at least one hydroxyl group, straight or branched C1-10 ester including at least one hydroxyl group, straight or branched C1-10 ketone including at least one hydroxyl group, straight or branched C1-10 carboxylic acid including at least one hydroxyl group, and straight or branched C1-10 acetal including at least one hydroxyl group.
    Type: Grant
    Filed: February 22, 2002
    Date of Patent: April 24, 2007
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Keun Kyu Kong, Min Ho Jung, Geun Su Lee, Ki Ho Balk
  • Patent number: 7202011
    Abstract: Disclosed is a photosensitive polymer comprising pentafluoromethylvinyl ether derivative monomer having the formula: wherein R may be an alkoxy carbonyl, alkylsilane, a fluorine-substituted or unsubstituted C3–C20 alkyl carbonyl, a fluorine-substituted or unsubstituted C3–C20 cycloalkylcarbonyl or a fluorine-substituted or unsubstituted benzoyl substituent group. The photosensitive polymer is the polymerization product of the pentafluoromethylvinyl ether derivative monomer and at least one additional monomer selected from the group consisting of (meth)acrylic acid, (meth)acrylate, styrene, norbornene, tetrafluoroethylene and maleic anhydride monomers. The photosensitive polymer may be used in photoresist compositions for exposure light sources having a predominant wavelength of less than 157 nm.
    Type: Grant
    Filed: April 28, 2003
    Date of Patent: April 10, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Kwang-Sub Yoon, Sang-Gyun Woo, Ki-Yong Song, Sang-jun Choi
  • Patent number: 7192686
    Abstract: Carborane based PAG's are bulky, produce a strong and large superacid, and have polarities that are compatible with the chemically amplified polymers typically used in photoresists. Carborane based PAG's also provide another broad class of bulky PAG's that may be used in photoresist formulations that offer flexibility in acid strength and polarity through changes in chemical structure. These PAG's may be used with EUV wavelengths, 157 nm, or 193 nm. Resolution and critical dimension control may be improved through the use of carborane based PAG's.
    Type: Grant
    Filed: March 31, 2004
    Date of Patent: March 20, 2007
    Assignee: Intel Corporation
    Inventor: Robert P. Meagley
  • Patent number: 7179582
    Abstract: A radical polymerizable composition comprising (A) an alkali-soluble resin containing a radical polymerizable group, (B) a radical polymerizable compound, and (C) a radical initiator, wherein reactivity of a polymerizable group of the polymerizable compound 4B) to a polymerizable group of the polymerizable compound (B) is larger than reactivity of a polymerizable group of the polymerizable compound (B) to a radical polymerizable group of the alkali-soluble resin (A), and a reactivity of a radical polymerizable group of the alkali-soluble resin (A) to a polymerizable group of the polymerizable compound (B) is larger than reactivity of a radical polymerizable group of the alkali-soluble resin (A) to a radical polymerizable group of the alkali-soluble resin (A).
    Type: Grant
    Filed: July 28, 2004
    Date of Patent: February 20, 2007
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Ryuki Kakino, Kazuto Kunita
  • Patent number: 7175963
    Abstract: A resin which comprises (1) at least one structural unit selected from the group consisting of a structural unit derived from 3-hydroxy-1-adamantyl (meth)acrylate, a structural unit derived from 3,5-dihydroxy-1-adamantyl (meth)acrylate, a structural unit derived from (meth)acryloyloxy-?-butyrolactone having a lactone ring optionally substituted by alkyl, a structural unit of the formula (Ia) and a structural unit of the formula and (2) a structural unit of the formula (II) 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; and also provides a chemical amplification type positive resist composition comprising a resin defined above and an acid generator.
    Type: Grant
    Filed: September 30, 2004
    Date of Patent: February 13, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yusuke Fuji, Yoshiyuki Takata, Isao Yoshida
  • Patent number: 7160666
    Abstract: A photosensitive resin composition of the present invention comprises (A) a resin having a repeating unit represented by formula (IA) and a repeating unit containing an acid decomposable group and copolymerizable with formula (IA), which is decomposed under the action of an acid to increase the solubility in an alkali developer, (B1) a compound capable of generating an aliphatic or aromatic sulfonic acid substituted by at least one fluorine atom upon irradiation with actinic rays or radiation, (B2) a compound capable of generating an aliphatic or aromatic sulfonic acid containing no fluorine atom, or an aliphatic or aromatic carboxylic acid upon irradiation with actinic rays or radiation, and (C) a solvent.
    Type: Grant
    Filed: March 5, 2003
    Date of Patent: January 9, 2007
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuyoshi Mizutani, Shinichi Kanna
  • Patent number: 7157204
    Abstract: A soluble polyimide for a photosensitive polyimide precursor and a photosensitive polyimide precursor composition including the soluble polyimide, wherein the soluble polyimide contains hydroxyl and acetyl moieties and at least one reactive end-cap group at one or both ends of the polymer chain. The photosensitive polyimide precursor composition comprises the soluble polyimide, a polyamic acid containing at least one reactive end-cap group at one or both ends of the polymer chain, a photo acid generator (PAG) and optionally a dissolution inhibitor. Since the polyimide film of the present invention exhibits excellent thermal, electric and mechanical properties, it can be used as insulating films or protective films for various electronic devices. A pattern with a high resolution may be formed even on the polyamide film having a thickness of above 10 ?m.
    Type: Grant
    Filed: November 7, 2003
    Date of Patent: January 2, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Myung Sup Jung, Yong Young Park, Sung Kyung Jung, Sang Yoon Yang
  • Patent number: 7147984
    Abstract: Disclosed is a positive-working chemical-amplification photoresist composition used in the patterning works in the manufacture of semiconductor devices, with which quite satisfactory patterning of a photoresist layer can be accomplished even on a substrate surface provided with an undercoating film of silicon nitride, phosphosilicate glass, borosilicate glass and the like in contrast to the prior art using a conventional photoresist composition with which satisfactory patterning can hardly be accomplished on such an undercoating film. The photoresist composition comprises, besides a film-forming resin capable of being imparted with increased solubility in an alkaline solution by interacting with an acid and a radiation-sensitive acid-generating compound, a phosphorus-containing oxo acid such as phosphoric acid and phosphonic acid or an ester thereof.
    Type: Grant
    Filed: March 29, 2004
    Date of Patent: December 12, 2006
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroto Yukawa, Katsumi Oomori, Ryusuke Uchida, Yukihiro Sawayanagi
  • Patent number: 7129015
    Abstract: A polymer used for a negative type resist composition having a first repeating unit of a Si-containing monomer unit, a second repeating unit having a hydroxy group or an epoxy ring and copolymerized with the first repeating unit is provided. The first repeating unit is represented by the following formula: wherein R1 is a hydrogen atom or a methyl group, X is a C1–C4 alkyl or alkoxy group, and n is an integer from 2 to 4. Also, there is provided a negative type resist composition including the polymer which is an alkali soluble base polymer, a photoacid generator and a crosslinking agent cross linkable in the presence of an acid.
    Type: Grant
    Filed: November 6, 2003
    Date of Patent: October 31, 2006
    Assignee: Samsung Electronics Co., Ltd.
    Inventor: Sang-jun Choi
  • 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: 7105271
    Abstract: A negative resist composition and a method for patterning semiconductor devices using the composition are provided. The negative resist composition contains an alkali-soluble hydroxy-substituted base polymer, a silicon-containing crosslinker having an epoxy ring, and a photoacid generator. In the method for patterning semiconductor devices, fine patterns are formed according to a bi-layer resist process using the negative resist composition.
    Type: Grant
    Filed: March 26, 2003
    Date of Patent: September 12, 2006
    Assignee: Samsung Electronics, Co., LTD
    Inventor: Sang-Jun Choi
  • Patent number: 7083893
    Abstract: Photoresist polymers and photoresist compositions are disclosed. A photoresist polymer represented by Formula 1 and a photoresist composition containing the same have excellent etching resistance, thermal resistance and adhesive property, and high affinity to an developing solution, thereby improving LER (line edge roughness). wherein X1, X2, R1, R2, m, n, a, b and c are as defined in the description.
    Type: Grant
    Filed: November 21, 2003
    Date of Patent: August 1, 2006
    Assignee: Hynix Semiconductor Inc.
    Inventor: Geun Su Lee
  • Patent number: 7081325
    Abstract: Photoresist polymers and photoresist compositions containing the same are disclosed. A negative photoresist composition containing a photoresist polymer comprising a repeating unit represented by Formula 4 prevents collapse of patterns when photoresist patterns of less than 50 nm are formed. Accordingly, the disclosed negative photoresist composition is very effective for a photolithography process using EUV (Extreme Ultraviolet, 13 nm) light source. wherein R1, R2, R3, R4, R5, R6, R7, a, b and c are as defined in the description.
    Type: Grant
    Filed: November 21, 2003
    Date of Patent: July 25, 2006
    Assignee: Hynix Semiconductor Inc.
    Inventors: Sung Koo Lee, Jae Chang Jung
  • 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: 7078156
    Abstract: A negative resist composition and a patterning method for semiconductor devices using the composition are provided. In one aspect, a negative resist composition comprises an alkali-soluble base polymer having an epoxy ring substituent, a silicon-containing crosslinker having multiple hydroxy groups, and a photoacid generator. In another aspect, a patterning method includes using the negative resist composition in a bi-layer resist process to form fine patterns.
    Type: Grant
    Filed: March 24, 2003
    Date of Patent: July 18, 2006
    Assignee: Samsung Electronics Co., Ltd.
    Inventor: Sang-Jun Choi
  • Patent number: 7049044
    Abstract: 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: Grant
    Filed: December 19, 2002
    Date of Patent: May 23, 2006
    Assignee: The University of North Carolina at Charlotte
    Inventors: Kenneth Gonsalves, Mohammed Azam Ali
  • Patent number: 7033728
    Abstract: 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: Grant
    Filed: December 29, 2003
    Date of Patent: April 25, 2006
    Assignee: AZ Electronic Materials USA Corp.
    Inventor: Ralph R. Dammel
  • Patent number: 7033729
    Abstract: Disclosed are a light absorbent agent polymer for organic anti-reflective coating which can prevent diffused reflection of lower film layer or substrate and reduce standing waves caused by variation of thickness of the photoresist itself, thereby, increasing uniformity of the photoresist pattern, in a process for forming ultra-fine patterns of photoresist for photolithography by using 193 nm ArF among processes for manufacturing semiconductor device, and its preparation method. Also, the present invention discloses an organic anti-reflective coating composition comprising the light absorbent agent polymer for the organic anti-reflective coating and a pattern formation process using the coating composition.
    Type: Grant
    Filed: October 12, 2004
    Date of Patent: April 25, 2006
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae-chang Jung, Keun Kyu Kong, Seok-kyun Kim
  • Patent number: 7022462
    Abstract: A photosensitive resin composition comprising (A) a carboxyl group-containing binder polymer which contains styrene or a styrene derivative as a copolymerized constituent, (B) a photo-polymerization initiator, and (C) a photo-polymerizable compound which has in its molecule at least one polymerizable ethylenically unsaturated bond and comprises a compound represented by the general formula (I) wherein R1 is a hydrogen atom or a methyl group, A is an alkylenoxy group, Z1 is a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an amino group, an alkylamino group, a dialkylamino group, a nitro group, a cyano group, a mercapto group, an alkylmercapto group, an allyl group, a hydroxyalkyl group, a carboxyalkyl group, an acyl group, an alkoxy group or a group containing an heterocyclic group, m is an integer of 4 to 20, and n is an integer of 0 to 5.
    Type: Grant
    Filed: March 2, 2000
    Date of Patent: April 4, 2006
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Takeshi Oohashi, Chikara Ishikawa
  • Patent number: 7008749
    Abstract: 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: Grant
    Filed: November 5, 2001
    Date of Patent: March 7, 2006
    Assignee: The University of North Carolina at Charlotte
    Inventor: Kenneth E. Gonsalves
  • Patent number: 7001706
    Abstract: 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: Grant
    Filed: July 16, 2004
    Date of Patent: February 21, 2006
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamaguchi, Makoto Akita, Isao Yoshida