Polyolefin Or Halogen Containing Patents (Class 430/907)
  • Patent number: 6974655
    Abstract: 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: Grant
    Filed: September 3, 2002
    Date of Patent: December 13, 2005
    Assignee: Infineon Technologies AG
    Inventors: Jörg Rottstegge, Christoph Hohle, Christian Eschbaumer, Michael Sebald, Wolf-Dieter Domke
  • Patent number: 6964840
    Abstract: A radiation-sensitive resin composition comprising an acid-labile group-containing resin and a photoacid generator is disclosed. The resin has a structure of the formula (1), wherein R1 represents a hydrogen atom, a monovalent acid-labile group, an alkyl group having 1-6 carbon atoms which does not have an acid-labile group, or an alkylcarbonyl group having 2-7 carbon atoms which does not have an acid-labile group, X1 represents a linear or branched fluorinated alkyl group having 1-4 carbon atoms, and R2 represents a hydrogen atom, a linear or branched alkyl group having 1-10 carbon atoms, or a linear or branched fluorinated alkyl group having 1-10 carbon atoms. The resin composition exhibits high transmittance of radiation, high sensitivity, resolution, and pattern shape, and is useful as a chemically amplified resist in producing semiconductors at a high yield.
    Type: Grant
    Filed: June 16, 2004
    Date of Patent: November 15, 2005
    Assignees: JSR Corporation, International Business Machines Corporation
    Inventors: Yukio Nishimura, Noboru Yamahara, Masafumi Yamamoto, Toru Kajita, Tsutomu Shimokawa, Hiroshi Ito
  • Patent number: 6962768
    Abstract: 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: Grant
    Filed: March 12, 2004
    Date of Patent: November 8, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyun-Woo Kim, Sang-Gyun Woo
  • Patent number: 6951705
    Abstract: Nitrile/vinyl ether-containing polymers for photoresist compositions and microlithography methods employing the photoresist compositions are described. These photoresist compositions comprise 1) at least one ethylenically unsaturated compound comprised of a vinyl ether and 2) a nitrile-containing compound, e.g., acrylonitrile, which together impart high ultraviolet (UV) transparency and developability in basic media. In some embodiments, these photoresist compositions further comprise a fluoroalcohol group. The photoresist compositions of this invention have, high UV transparency, particularly at short wavelengths, e.g., 157 nm and 193 nm, which property makes them useful for lithography at these short wavelengths.
    Type: Grant
    Filed: May 4, 2001
    Date of Patent: October 4, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Michael Fryd, Periyasamy Mookkan, Frank Leonard Schadt, III
  • Patent number: 6949323
    Abstract: Resist compositions comprising as the base resin a polymer using tert-amyloxystyrene as a reactive group which is decomposable under the action of an acid to increase solubility in alkali have advantages including a significantly enhanced contrast of alkali dissolution rate before and after exposure, a high sensitivity, and a high resolution in the baking temperature range of 100-110° C. which is unachievable with tert-butoxystyrene. The compositions are best suited as a chemically amplified resist material for micropatterning in the manufacture of VLSI.
    Type: Grant
    Filed: October 30, 2002
    Date of Patent: September 27, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takanobu Takeda, Osamu Watanabe, Kazunori Maeda, Hiroshi Miyakoshi
  • Patent number: 6949325
    Abstract: A negative resist composition is disclosed, wherein the resist composition includes a polymer having at least one fluorosulfonamide monomer unit having one of the following two formulae: wherein: M is a polymerizable backbone moiety; Z is a linking moiety selected from the group consisting of —C(O)O—, —C(O)—, —OC(O)—, —O—C(O)—C(O)—O—, or alkyl; P is 0 or 1; R1 is a linear or branched alkyl group of 1 to 20 carbons; R2 is hydrogen, fluorine, a linear or branched alkyl group of 1 to 6 carbons, or a semi- or perfluorinated linear or branched alkyl group of 1 to 6 carbons; and n is an integer from 1 to 6.
    Type: Grant
    Filed: September 16, 2003
    Date of Patent: September 27, 2005
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara Rao Varanasi
  • Patent number: 6933096
    Abstract: A photosensitive polymer including fluorine, a resist composition containing the same and a patterning method for IC fabrication using the resist composition are provided. The photosensitive polymer having at least one selected from the group consisting of fluorine-substituted or unsubstituted alkyl ester, tetrahydropyranyl ester, tetrahydrofuranyl ester, nitrile, amide, carbonyl and hexafluoro alkyl having a hydrophilic group, and a trifluorovinyl derivative monomer as a repeating unit and having a weight average molecular weight of about 3,000 to about 100,000. The photosensitive polymer exhibits high transmittance for a light source of F2 (157 nm), high dry etching resistance, and has characteristics suitable to realize an unitrafine pattern size.
    Type: Grant
    Filed: November 21, 2003
    Date of Patent: August 23, 2005
    Assignee: Samsung Electronics, Co., Ltd.
    Inventors: Kwang-Sub Yoon, Ki-Yong Song
  • Patent number: 6933095
    Abstract: A copolymer of an acrylate monomer containing fluorine at ?-position with a fluorinated hydroxystyrene derivative is highly transparent to VUV radiation and resistant to plasma etching. A resist composition using the polymer as a base resin is sensitive to high-energy radiation below 200 nm, has excellent sensitivity, resolution, transparency, substrate adhesion and plasma etching resistance, and is suited for lithographic microprocessing.
    Type: Grant
    Filed: June 25, 2002
    Date of Patent: August 23, 2005
    Assignees: 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, Michitaka Ootani, Satoru Miyazawa, Kentaro Tsutsumi, Kazuhiko Maeda
  • Patent number: 6929897
    Abstract: 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: Grant
    Filed: August 19, 2004
    Date of Patent: August 16, 2005
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Patrick Foster, Gregory Spaziano, Binod B De
  • Patent number: 6927010
    Abstract: The present invention employs a polymer material exhibiting a low absorbance in the wavelength range of a vacuum ultraviolet (VUV) light to allow the improved ultra-fine process to be realized. In an exposure method for selectively exposing a resist layer to an ultraviolet light to pattern the resist layer into a predetermined shape, a polymer material, to which a cyclopentane group is introduced, is used as a polymer material constituting the resist layer, wherein at least one hydrogen atom of the introduced cyclopentane group is substituted by at least one selected from the group consisting of a fluorine atom, a trifluoromethyl group and a difluoromethylene group.
    Type: Grant
    Filed: December 12, 2002
    Date of Patent: August 9, 2005
    Assignee: Sony Corporation
    Inventor: Nobuyuki Matsuzawa
  • Patent number: 6919160
    Abstract: 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: Grant
    Filed: February 20, 2003
    Date of Patent: July 19, 2005
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Atteye Houssein Abdourazak, Thomas John Markley
  • Patent number: 6916598
    Abstract: This invention discloses compositions that can be polymerized/crosslinked imagewise upon exposure to ionization radiation such as x-ray, electron beam, ion beam, and gamma-ray. This invention also discloses methods of use for these compositions for microfabrication of ceramics, for stereolithography, and for x-ray, e-beam, and ion-beam lithography which can be used for photoresists.
    Type: Grant
    Filed: March 21, 2003
    Date of Patent: July 12, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Ying Wang
  • Patent number: 6916590
    Abstract: The following resist composition which is excellent particularly in transparency to light beams and dry etching properties and gives a resist pattern excellent in sensitivity, resolution, evenness, heat resistance, etc., as a chemical amplification type resist, is presented. A resist composition which comprises a fluoropolymer (A) having repeating units represented by a structure formed by the cyclopolymerization of one molecule of a fluorinated diene and one molecule of a monoene, in which the monoene unit in each repeating unit has a blocked acid group capable of regenerating the acid group by the action of an acid, an acid-generating compound (B) which generates an acid upon irradiation with light, and an organic solvent (C).
    Type: Grant
    Filed: December 19, 2002
    Date of Patent: July 12, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Isamu Kaneko, Yoko Takebe, Shun-ichi Kodama
  • Patent number: 6916592
    Abstract: 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: Grant
    Filed: March 25, 2003
    Date of Patent: July 12, 2005
    Assignees: 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
  • Patent number: 6908724
    Abstract: There is provided a novel fluorine-containing polymer having an acid-reactive group which has a high transparency against energy rays (radioactive rays) in a vacuum ultraviolet region (157 nm), and further there are provided a material for fluorine-containing base polymer prepared from the polymer and suitable for a photoresist and a chemically amplifying type resist composition obtained therefrom. The polymer has a number average molecular weight of from 1,000 to 1,000,000 and represented by the formula: —(M1)—(M2)—(A)—, wherein M1 is a structural unit having an acid-labile or acid-degradable functional group, M2 is a structural unit of fluorine-containing acryl ester, A is a structural unit derived from other copolymerizable monomer, the percent by mole ratio M1/M2 is 1 to 99/99 to 1 and the polymer comprises from 1 to 99% by mole of the structural unit M1, from 1 to 99% by mole of the structural unit M2 and from 0 to 98% by mole of the structural unit A1.
    Type: Grant
    Filed: October 3, 2002
    Date of Patent: June 21, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Takayuki Araki, Meiten Koh, Yoshito Tanaka, Takuji Ishikawa, Hirokazu Aoyama, Tetsuo Shimizu
  • Patent number: 6893792
    Abstract: The present invention provides a positive resist composition comprising a resin 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 an acid generator, wherein the content of halogen atoms in the resin is 40% by weight or more, at least one of structural units constituting the resin is a structural unit having an alicyclic hydrocarbon skeleton, and the structural unit having an alicyclic hydrocarbon skeleton contains therein at least one group rendering the resin soluble in an alkali aqueous solution by the action of an acid, and at least one halogen atom.
    Type: Grant
    Filed: February 14, 2003
    Date of Patent: May 17, 2005
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiko Miya, Kouji Toishi, Kazuhiko Hashimoto
  • Patent number: 6887643
    Abstract: A photosensitive resin precursor composition exhibiting an excellent film thickness uniformity contains: a heat resistant resin precursor polymer; a radiation sensitive compound; and a solvent expressed by formula (1): R1 represents an alkyl group having a carbon number in the range of 1 to 3. R2, R3, R4, and R5 each represent hydrogen or an alkyl group having a carbon number in the range of 1 to 3, and l represents an integer in the range of 0 to 3.
    Type: Grant
    Filed: July 22, 2003
    Date of Patent: May 3, 2005
    Assignee: Toray Industries, Inc.
    Inventors: Yoji Fujita, Mitsuhito Suwa, Masao Tomikawa
  • Patent number: 6884564
    Abstract: Fluorinated polymers, photoresists and associated processes for microlithography are described. These polymers and photoresists are comprised of esters derived from fluoroalcohol functional groups that simultaneously impart high ultraviolet (UV) transparency and developability in basic media to these materials. The materials of this invention have high UV transparency, particularly at short wavelengths, e.g., 157 nm, which makes them highly useful for lithography at these short wavelengths.
    Type: Grant
    Filed: October 25, 2002
    Date of Patent: April 26, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Andrew E. Feiring, Jerald Feldman, Frank L. Schadt, III, Gary Newton Taylor
  • Patent number: 6884562
    Abstract: Positive photoresists and associated processes for microlithography in the ultraviolet (UV) and violet are disclosed. The photoresists comprise (a) a branched copolymer containing protected acid groups and (b) at least one photoacid generator. The photoresists have high transparency throughout the UV, good development properties, high plasma etch resistance and other desirable properties, and are useful for microlithography in the near, far, and extreme UV, particularly at wavelengths less than or equal to 365 nm.
    Type: Grant
    Filed: October 26, 1999
    Date of Patent: April 26, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Frank Leonard Schadt, III, Michael Fryd, Mookkan Periyasamy
  • Patent number: 6881531
    Abstract: An exposure method comprising a step of subjecting a resist layer to selective exposure to an ultraviolet light and forming a predetermined pattern in the resist layer, wherein a polymer material having introduced thereinto a cyclohexane group is used as a polymer material constituting the resist layer wherein all hydrogen atoms bonded to four continuously adjacent carbon atoms in the cyclohexane group are substituted by fluorine atoms. The use of a polymer material having a lowered absorption in the wavelength range of a vacuum ultraviolet (VUV) light in the resist material or resist layer enables a more improved ultra-fine processing than before.
    Type: Grant
    Filed: December 12, 2002
    Date of Patent: April 19, 2005
    Assignee: Sony Corporation
    Inventor: Nobuyuki Matsuzawa
  • Patent number: 6878502
    Abstract: 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: Grant
    Filed: July 2, 2002
    Date of Patent: April 12, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuyoshi Mizutani, Shinichi Kanna
  • Patent number: 6875552
    Abstract: The present invention provides a photoresist composition that reduces standing wave and side wall roughness. The composition comprises a first photoresist X and a second photoresist Y. The first photoresist X absorbs at a higher wavelength than the second photoresist Y. The second photoresist Y has a lower glass transitional temperature than the first photoresist X. A method for making the photoresist composition is also provided.
    Type: Grant
    Filed: August 9, 2002
    Date of Patent: April 5, 2005
    Assignee: Micron Technology, Inc.
    Inventor: Yoshiki Hishiro
  • Patent number: 6875556
    Abstract: A resist composition comprising as the base resin a blend of a fluorinated polymer which is sensitive to high-energy radiation and highly transparent at a wavelength of up to 200 nm and a sulfonate-containing polymer exhibiting a high contrast upon alkali dissolution is improved in transparency and alkali dissolution contrast as well as plasma etching resistance.
    Type: Grant
    Filed: October 23, 2003
    Date of Patent: April 5, 2005
    Assignees: 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, Haruhiko Komoriya, Satoru Miyazawa
  • Patent number: 6872514
    Abstract: 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: Grant
    Filed: March 25, 2003
    Date of Patent: March 29, 2005
    Assignees: 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
  • Patent number: 6866983
    Abstract: A resist composition comprising a blend of a polymer comprising recurring units k and m of formula (1) wherein R1 and R2 each are hydrogen or an acid labile group, 0<k<1, 0<m<1 and 0<k+m?1, and another polymer comprising recurring units having carboxyl groups whose hydrogen atoms are replaced by acid labile groups as a base resin forms a resist film which is improved in transparency, alkali dissolution contrast and plasma etching resistance.
    Type: Grant
    Filed: April 4, 2003
    Date of Patent: March 15, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai
  • Patent number: 6864037
    Abstract: A copolymer of an acrylic monomer having at least one C6-20 alicyclic structure with a norbornene derivative or styrene monomer having a hexafluoroalcohol pendant is highly transparent to VUV radiation and resistant to plasma etching. A resist composition using the polymer as a base resin is sensitive to high-energy radiation below 200 nm, has excellent sensitivity, transparency and dry etching resistance, and is suited for lithographic microprocessing.
    Type: Grant
    Filed: June 25, 2002
    Date of Patent: March 8, 2005
    Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co. Ltd., Central Glass Co., Ltd.
    Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Michitaka Ootani, Satoru Miyazawa, Kentaro Tsutsumi, Kazuhiko Maeda
  • Patent number: 6861197
    Abstract: A base polymer having incorporated an ester group having a fluorinated alicyclic unit is provided. A resist composition comprising the polymer is sensitive to high-energy radiation, and has excellent sensitivity at a wavelength of less than 200 nm, significantly improved transparency by virtue of the fluorinated alicyclic units incorporated as well as satisfactory plasma etching resistance. The resist composition has a low absorption at the exposure wavelength of a F2 laser and is ideal as a micropatterning material in VLSI fabrication.
    Type: Grant
    Filed: February 28, 2002
    Date of Patent: March 1, 2005
    Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.
    Inventors: Yuji Harada, Jun Watanabe, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Michitaka Ootani, Satoru Miyazawa, Kentaro Tsutsumi, Kazuhiko Maeda
  • Patent number: 6861199
    Abstract: 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: Grant
    Filed: June 30, 2003
    Date of Patent: March 1, 2005
    Assignee: Hynix Semiconductor
    Inventor: Geun Su Lee
  • Patent number: 6858760
    Abstract: A fluorine-containing cyclic compound is represented by the formula 1: wherein each of R1, R2 and R3 independently represents a hydrogen, alkyl group, fluorine, fluoroalkyl group or hexafluorocarbinol group, wherein at least one of the hexafluorocarbinol groups may partly or totally be protected with a protecting group, and wherein the protecting group is (a) a straight-chain, branched or cyclic hydrocarbon group having a carbon atom number of 1-25 or (b) an aromatic hydrocarbon group and optionally contains a fluorine atom, oxygen atom, nitrogen atom or carbonyl bond.
    Type: Grant
    Filed: February 20, 2004
    Date of Patent: February 22, 2005
    Assignee: Central Glass Company, Limited
    Inventors: Haruhiko Komoriya, Satoru Miyazawa, Katsunori Kawamura, Satoru Kobayashi, Kazuhiko Maeda
  • Patent number: 6858379
    Abstract: New photoresists are provided that are suitable for short wavelength imaging, including sub-200 nm such as 157 nm. In one aspect, resists of the invention comprise a fluorine-containing polymer, a photoactive component, and one or more additional components of an amine or other basic composition, a dissolution inhibitor compound, a surfactant or leveling agent, or a plasticizer material. In another aspect, resists of the invention contain a fluorine-containing resin and one or more photoacid generator compounds, particularly non-aromatic onium salts and imidosulfonates, and other non-ionic photoacid generator compounds.
    Type: Grant
    Filed: March 20, 2002
    Date of Patent: February 22, 2005
    Assignee: Shipley Company, L.L.C.
    Inventors: Anthony Zampini, Charles R. Szmanda, Gary N. Taylor, James F. Cameron, Gerhard Pohlers
  • Patent number: 6858371
    Abstract: Photoresist monomers, photoresist polymers prepared thereof, and photoresist compositions using the polymer are disclosed. More specifically, photoresist polymers comprising maleimide monomer represented by Formula 1, and a composition comprising the polymer thereof are disclosed. The photoresist composition has excellent etching resistance, heat resistance and adhesiveness, and can be developed in an aqueous tetramethylammonium hydroxide (TMAH) solution. As the composition has low light absorbance at 193 nm and 157 nm wavelength, and it is suitable for a process using ultraviolet light source such as VUV (157 nm) wherein, X1, X2, R1, R2 and R3 are defined in the specification.
    Type: Grant
    Filed: February 21, 2002
    Date of Patent: February 22, 2005
    Assignee: Hynix Semiconductor Inc.
    Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Cha Won Koh, Ki Soo Shin
  • Patent number: 6855480
    Abstract: Disclosed are photoimageable compositions having improved stripping properties as well as methods for manufacturing printed wiring boards using such photoimageable compositions.
    Type: Grant
    Filed: April 6, 2002
    Date of Patent: February 15, 2005
    Assignee: Shipley Company, L.L.C.
    Inventors: Stephen H. Wheeler, Randall W. Kautz, Robert K. Barr
  • Patent number: 6855475
    Abstract: Disclosed are photoresist compositions suitable for imaging with sub 200 nm wavelength radiation including as polymerized units one or more monomers having an electronegative substituent and an ester group containing certain leaving groups. Also disclosed are methods of providing photoresist relief images using the photoresist compositions.
    Type: Grant
    Filed: March 19, 2002
    Date of Patent: February 15, 2005
    Assignee: Shipley Company, L.L.C.
    Inventor: Charles R. Szmanda
  • Patent number: 6852467
    Abstract: A positive resist composition comprising: (A) a fluorine group-containing resin having: a structure wherein at least one of the main chain and the side chain of the polymer skeleton has at least one fluorine atom; and having a group capable of decomposing under the action of an acid to increase the solubility in an alkali developer; (B) a compound capable of generating an acid upon irradiation with one of actinic ray and radiation, and (C) a surfactant containing at least one of a silicon atom and a fluorine atom.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: February 8, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Shoichiro Yasunami, Kazuyoshi Mizutani, Shinichi Kanna
  • Patent number: 6849377
    Abstract: 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: Grant
    Filed: March 27, 2002
    Date of Patent: February 1, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Andrew E. Feiring, Frank L. Schadt, III
  • Patent number: 6846610
    Abstract: Provided is a positive photosensitive resin composition comprising (A) a polymer which has alicyclic hydrocarbon skeleton and decomposes under the action of an acid to be rendered soluble in alkali, (B) a compound which generates an acid upon irradiation with actinic rays, (C) a nitrogen-containing basic compound, (D) at least one of a fluorine-containing surfactant and a silicon-containing surfactant and (E) a solvent. The composition can exhibit better characteristics when the solvent (E) is a combination of specified solvents.
    Type: Grant
    Filed: December 10, 2002
    Date of Patent: January 25, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Kenichiro Sato, Toshiaki Aoai
  • Patent number: 6835528
    Abstract: A photoresist which has high transparency at a wavelength of 157 nm and which therefore permits a greater layer thickness in photolithographic processes for the production of microchips. The photoresist includes a polymer that is prepared from a first fluorinated comonomer that includes a group cleavable under acid catalysis, a second comonomer that includes an anchor group, and a third comonomer whose degree of fluorination is tailored to the second comonomer so that at least one of the comonomers acts as an electron donor and the others act as electron acceptors in the free radical polymerization. Thus, in spite of a high degree of fluorination, the polymer can be prepared in a simple manner and in high yield.
    Type: Grant
    Filed: January 31, 2003
    Date of Patent: December 28, 2004
    Assignee: Infineon Technologies AG
    Inventor: Jörg Rottstegge
  • Patent number: 6835524
    Abstract: Polymers comprising recurring units of an acrylic derivative of fluorinated backbone represented by formula (1) are novel. R1, R2 and R3 are independently H, F, C1-20 alkyl or fluorinated C1-20 alkyl, at least one of R1, R2 and R3 contains fluorine, and R4 is a hydrophilic group. Using the polymers, chemical amplification positive resist compositions featuring low absorption of F2 excimer laser light are obtained.
    Type: Grant
    Filed: February 15, 2001
    Date of Patent: December 28, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Jun Watanabe, Yuji Harada
  • Patent number: 6835530
    Abstract: There is provided a base material for lithography that is capable of achieving superior film formation characteristics, while maintaining good light absorption characteristics. The base material for lithography comprises (a) a cross linking agent formed from a specific nitrogen containing compound, (b) a copolymer comprising two types of (meth)acrylate ester units as represented by the general formulas (1) and (2) shown below, and (c) an organic solvent: wherein, R1 represents a hydroxyl group or a carboxyl group or the like, and X represents an alkyl chain of 1 to 4 carbon atoms; and wherein, R2 represents a hydroxyl group or a carboxyl group or the like, Y represents —SO2—, —CO— or —SO—; and n represents a number from 1 to 4.
    Type: Grant
    Filed: August 26, 2003
    Date of Patent: December 28, 2004
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Etsuko Nakamura, Jun Koshiyama, Takeshi Tanaka
  • Patent number: 6830871
    Abstract: A chemical amplification type resist composition comprising: (a) a resin comprising repeating units having a side chain containing the specific partial structure and which increases the solubility in an alkaline developing solution by the action of an acid, (b) a compound capable of generating an acid upon irradiation with actinic rays or a radiation, (c) a low-molecular compound having a molecular weight of 3,000 or lower, wherein the value determined with the specific calculation formula is from 0.1 to 0.5, and (d) a solvent.
    Type: Grant
    Filed: August 18, 2003
    Date of Patent: December 14, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinichi Kanna, Kazuyoshi Mizutani, Tomoya Sasaki
  • Patent number: 6830872
    Abstract: Disclosed is planographic printing plate precursor comprising a support having disposed thereon an image forming layer containing a fluorine macromolecular compound having a structural unit derived from a monomer represented by the following general formula (I). In the general formula (I), R0 represents a hydrogen atom, a methyl group, a cyano group or a halogen atom. X represents a single bond or a divalent connecting group. R1 to R6 each independently represent a hydrogen atom, an alkyl group, a fluorine atom or an alkyl group in which at least one hydrogen atom is substituted with a fluorine atom. Further, at least one of R1 to R6 represents a fluorine atom or an alkyl group in which at least one hydrogen atom is substituted with a fluorine atom.
    Type: Grant
    Filed: September 20, 2002
    Date of Patent: December 14, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuyoshi Mizutani, Shiro Tan
  • Patent number: 6830869
    Abstract: A pattern formation material of this invention contains a base polymer including a first unit represented by Chemical Formula 1 and a second unit represented by Chemical Formula 2 and, and an acid generator: wherein R1 and R3 are the same or different and are a hydrogen atom, a chlorine atom, a fluorine atom, an alkyl group or an alkyl group including a fluorine atom; R2 is an atom or a group that is not released by an acid and is selected from the group consisting of a hydrogen atom, an alkyl group, a cyclic aliphatic group, an aromatic group, a heterocycle, an ester group and an ether group; R4 is a protecting group released by an acid; m is an integer of 0 through 5; and a and b satisfy 0<a<1, 0<b<1 and 0<a+b≦1.
    Type: Grant
    Filed: April 29, 2003
    Date of Patent: December 14, 2004
    Assignee: Atsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Tsuyohiko Fujigaya
  • Patent number: 6824955
    Abstract: A resist composition comprising a copolymer of an acrylic ester monomer containing fluorine at &agr;-position with a norbornene derivative containing oxygen or sulfur within the norbornene ring as a base resin is sensitive to high-nergy radiation below 200 nm, has excellent sensitivity, transparency and dry etching resistance, and is suited for lithographic microprocessing.
    Type: Grant
    Filed: December 26, 2002
    Date of Patent: November 30, 2004
    Assignees: 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
  • Publication number: 20040224251
    Abstract: The present invention provides a positive resist composition comprising
    Type: Application
    Filed: September 23, 2003
    Publication date: November 11, 2004
    Inventors: Kouji Toishi, Yasunori Uetani
  • Patent number: 6815145
    Abstract: A radiation sensitive resin composition including a photo-acid generator and an aliphatic polymer having one or more electron withdrawing groups adjacent to or attached to a carbon atom bearing a protected hydroxyl group, wherein the protecting group is labile in the presence of in situ generated acid is described. The radiation sensitive resin composition can be used as a resist suitable for image transfer by plasma etching and enable one to obtain an etching image having high precision with high reproducibility with a high degree of resolution and selectivity.
    Type: Grant
    Filed: October 16, 2002
    Date of Patent: November 9, 2004
    Assignee: Massachusetts Institute of Technology
    Inventor: Theodore H. Fedynyshyn
  • Patent number: 6811947
    Abstract: A positive resist composition comprising (A) a resin, which is decomposed by the action of an acid to increase solubility in an alkali developing solution, having a repeating unit represented by formula (Y) defined in the specification, (B) a compound capable of generating an acid upon irradiation of an actinic ray or radiation, and (C) a solvent.
    Type: Grant
    Filed: February 25, 2003
    Date of Patent: November 2, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuyoshi Mizutani, Tomoya Sasaki, Shinichi Kanna
  • Patent number: 6806027
    Abstract: Chemically amplified photoresists exhibit increased transparency at a wavelength of 157 nm. The chemically amplified photoresist includes a polymer containing first repeating units derived from a cinnamic acid or a cinnamic ester, which are at least monofluorinated or substituted by fluoroalkyl groups. Processes for structuring substituents using transparency enhancement of resist copolymers for 157 nm photolithography using fluorinated cinnamic acid derivatives are also included.
    Type: Grant
    Filed: July 30, 2002
    Date of Patent: October 19, 2004
    Assignee: Infineon Technologies AG
    Inventors: Christoph Hohle, Jörg Rottstegge, Christian Eschbaumer, Michael Sebald
  • Patent number: 6806026
    Abstract: A photoresist composition is provided that includes a polymer having at least one acrylate or methacrylate monomer having a formula: where R1 represents hydrogen (H), a linear or branched alkyl group of 1 to 20 carbons, or a semi- or perfluorinated linear or branched alkyl group of 1 to 20 carbons; and where R2 represents an unsubstituted aliphatic group or a substituted aliphatic group having zero or one trifluoromethyl (CF3) group attached to each carbon of the substituted aliphatic group, or a substituted or unsubstituted aromatic group; and where R3 represents hydrogen (H), methyl (CH3), trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated aliphatic chain; and where R4 represents trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated substituted or unsubstituted aliphatic group. A method of patterning a substrate using the photoresist composition is also provided herein.
    Type: Grant
    Filed: May 31, 2002
    Date of Patent: October 19, 2004
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Gregory Breyta, Phillip Brock, Richard A. DiPietro, Debra Fenzel-Alexander, Carl Larson, David R. Medeiros, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory M. Wallraff
  • Patent number: 6806029
    Abstract: A pattern formation material of this invention contains a base polymer including a first unit represented by Chemical Formula 1 and a second unit represented by Chemical Formula 2, and an acid generator: wherein R1 and R2 are the same or different and selected from the group consisting of a hydrogen atom, a chlorine atom, a fluorine atom, an alkyl group and an alkyl group including a fluorine atom; R3 is a protecting group released by an acid; m is an integer of 0 through 5; and a and b satisfy 0<a<1,0<b<1 and 0<a+b≦1.
    Type: Grant
    Filed: September 6, 2002
    Date of Patent: October 19, 2004
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Tsuyohiko Fujigaya
  • Patent number: 6803171
    Abstract: Disclosed are photoimageable compositions containing silsesquioxane binder polymers and photoactive compounds, methods of forming relief images using such compositions and methods of manufacturing electronic devices using such compositions. Such compositions are useful as photoresists and in the manufacture of optoelectronic devices.
    Type: Grant
    Filed: May 8, 2002
    Date of Patent: October 12, 2004
    Assignee: Shipley Company L.L.C.
    Inventors: Dana A. Gronbeck, George G. Barclay, Leo L. Linehan, Kao Xiong, Subbareddy Kanagasabapathy