WO2005036261A1 - Negative resist composition with fluorosulfonamide-containing polymer - Google Patents
Negative resist composition with fluorosulfonamide-containing polymer Download PDFInfo
- Publication number
- WO2005036261A1 WO2005036261A1 PCT/US2004/017114 US2004017114W WO2005036261A1 WO 2005036261 A1 WO2005036261 A1 WO 2005036261A1 US 2004017114 W US2004017114 W US 2004017114W WO 2005036261 A1 WO2005036261 A1 WO 2005036261A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resist composition
- resist
- material layer
- polymer
- group
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/18—Monomers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
- C08F220/387—Esters containing sulfur and containing nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D145/00—Coating compositions based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Coating compositions based on derivatives of such polymers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/107—Polyamide or polyurethane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/108—Polyolefin or halogen containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/128—Radiation-activated cross-linking agent containing
Definitions
- the present invention relates to a resist composition and, more particularly, to a negative resist composition that includes a polymer having at least one monomer unit that contains a fluorosulfonamide structure.
- Resists are generally comprised of a polymeric matrix, a radiation sensitive component, a casting solvent, and other performance enhancing additives.
- the polymeric portion of the resist should have a reasonable absorption at exposure wavelengths, and the resist composition must also possess suitable chemical and mechanical properties to enable transfer of the image from the patterned resist to an underlying substrate layer(s).
- an important parameter to be considered in the design of a resist material is the dissolution behavior of the material in the given developer.
- a patternwise exposed negative resist must be capable of appropriate dissolution response (i.e., selective dissolution in developer of unexposed areas) to yield the desired resist structure.
- TMAH 0.263 N tetramethyl ammonium hydroxide
- the resist should have a reasonable dissolution rate before exposure and little or no dissolution after exposure.
- acidic groups have been incorporated into the polymer structure.
- hydroxystyrene has been widely used as such an acidic group in negative resist designed for use with irradiation at a wavelength of 248 nm. Hydroxystyrene, however, is too absorbing at 193 nm wavelength.
- the present invention is directed to a negative-tone resist composition
- a negative-tone resist composition comprising a polymer, the polymer comprising at least one fluorosulfonamide monomer unit having one of the following two formulae:
- 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
- Ri is a linear or branched alkyl group of 1 to 20 carbons
- ⁇ 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
- n is an integer from 1 to 6.
- the resist composition of the invention may further comprise any one of a solvent, a radiation sensitive acid generator, a crosslinking agent, a quencher, and a surfactant.
- the invention is directed to a method of forming a patterned material layer on a substrate, the method comprising: (a) providing a substrate having a material layer on a surface; (b) applying the resist composition mentioned above to the substrate to form a resist layer on the material layer; (c) patternwise exposing the resist layer to imaging radiation; (d) removing portions of the resist layer not exposed to the imaging radiation in step (c) to create spaces in the resist layer corresponding to the pattern; and (e) removing portions of the material layer at the spaces formed in step (d), thereby forming the patterned material layer.
- the present invention is directed to a negative resist composition which comprises a polymer, the polymer comprising at least one monomer unit which includes a fluorosulfonamide group.
- Resist polymers with these fluorosulfonamide groups contain less fluorine than prior art resist polymers which include HFA, a feature which improves etch resistance of the resist material.
- the fluorosulfonamide group of the invention has a stronger acidity than the HFA group used in prior art resists. Therefore, in order to achieve the same dissolution rate in developer as prior art resists containing HFA, a lower concentration of the fluorosulfonamide group may be used in the resist polymer of the invention, further improving the etch resistance.
- the invention is specifically directed to a negative resist composition
- a polymer which comprises at least one fluorosulfonamide monomer unit preferably 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 ; Ri represents a linear or branched alkyl group of 1 to 20 carbons; R represents 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.
- the polymerizable backbone moiety, M include:
- R 3 represents hydrogen, a linear or branched alkyl group of 1 to 20 carbons, a semi- or perfluorinated linear or branched alkyl group of 1 to 20 carbons, or CN;
- fluorosulfonamide monomers include: (I) (I") (III)
- the polymer may further comprise a co-monomer unit which can participate in reactions which render the polymer insoluble in developer, such as a crosslinking co-monomer unit.
- co-monomer units include:
- the negative resist composition of the invention may further comprise any one of a solvent, a radiation sensitive acid generator, a crosslinking agent, a quencher, and a surfactant.
- Solvents well known to those skilled in the art may be employed in the resist formulation of the invention. Such solvents are used to dissolve the fluorosulfonamide-containing polymer and other components of the resist composition.
- Illustrative examples of such solvents include, but are not limited to: ethers, glycol ethers, aromatic hydrocarbons, ketones, esters and the like.
- Preferred solvents include propylene glycol monomethyl ether acetate, ethyl lactate, ⁇ -butyrolactone, and cyclohexanone.
- the radiation sensitive acid generators also known as photoacid generators, which may be used in the resist composition of the invention are compounds which will generate an acid upon exposure to energy. Any suitable photoacid generating agent may be used so long as a mixture of the aforementioned resist composition of the present invention and the photoacid generator dissolves sufficiently in an organic solvent and the resulting solution thereof can form a uniform film by a film-forming process such as spin coating or the like.
- Illustrative classes of such acid generators that can be employed in the present invention include, but are not limited to: onium salts, succinimide derivatives, diazo compounds, nitrobenzyl compounds, and the like.
- the acid generators should be such that they generate bulky acids upon exposure to energy. These bulky acids contain at least 4 carbon atoms.
- a preferred acid generator employed in the present invention is an onium salt, such as an iodonium salt or a sulfonium salt, and/or a succinimide derivative.
- Preferred acid generators include 4-(1 -butoxynaphthyl) tetrahydrothiophenium perfluorobutanesulfonate, triphenyl sulfonium perfluorobutanesulfonate, t-butylphenyl diphenyl sulfonium perfluorobutanesulfonate, 4-(1 -butoxynaphthyl) tetrahydrothiophenium perfluorooctanesulfonate, triphenyl sulfonium perfluorooctanesulfonate, t-butylphenyl diphenyl sulfonium perfluorooctanesulfonate, di(t-butylphenyl) iodonium perfluorobutane sulfonate, di(t-butylphenyl) iodonium perfluorohexane sulfonate, di
- photoacid generators may be used singly or in the form of a mixture of two or more.
- the specific photoacid generator selected will depend on the irradiation being used for patterning the resist. Photoacid generators are currently available for a variety of different wavelengths of light from the visible range to the X-ray range; thus, imaging of the resist can be performed using deep-UV, extreme-UV, e-beam, laser or any other irradiation source deemed useful.
- the crosslinking agents used in the invention may be a single compound or a combination of two or more compounds that generate stable carbocations in the presence of photogenerated acid to crosslink the sulfonamide-containing polymer. Typical crosslinking agents are any compound containing more than one of the following unit:
- R 4 represents hydrogen, or a linear or branched alkyl group, or an aromatic group.
- the preferred crosslinking agents are glycouril and derivatives thereof having the formula:
- R 5 -R 10 each represent hydrogen, or a linear or branched alkyl group, preferably an alkyl group of 1 to 8 carbons, or an aromatic group, preferably an aryl hydrocarbon group of 6 to 9 carbons.
- Preferred crosslinking agents include tetramethoxylmethyl glycouril (Powderlink, available from Cytec), methylpropyl Powderlink, and methylphenyl Powderlink. Combinations of two or more of these crosslinking agents may also be used as crosslinking agents.
- the quenchers that can be employed in the invention are weak bases which scavenge trace acids while not having an excessive impact on the performance of the negative-tone resist.
- quenchers include aromatic or aliphatic amines such as 2-phenylbenzimidazole or t-alkyl ammonium hydroxides such as t-butyl ammonium hydroxide (TBAH).
- the surfactants that can be employed in the invention are those that are capable of improving the coating homogeneity of the negative-tone resist compositions of the invention.
- Illustrative examples of such surfactants include fluorine-containing surfactants such as 3M's FC-430 and siloxane-containing surfactants such as Union Carbide's SILWET series and the like.
- the resist composition of the invention may contain (i) about 1 to about 30 wt.
- the resist composition may further contain a quencher, which is typically present in amounts of about 0.1 to about 1.0 wt.
- the sulfonamide-containing resist composition may be used as an imaging layer in the manufacture of semiconductor devices.
- the sulfonamide-containing imaging layer is applied by known means, such as spin-coating to a desired substrate.
- the substrate with the resist is then preferably baked (pre-exposure bake) to remove the solvent and improve the coherence of the resist layer.
- pre-exposure baking temperature is about 80 to about 150 °C.
- Typical resist thickness is about 100 to about 500 nm.
- the imaging layer is then exposed to an appropriate irradiation source. This is followed by post-exposure baking and development in an aqueous base developer, such as 0.263 N TMAH developer.
- the pattern from the resist structure may then be transferred to the material (e.g., ceramic, dielectric, metal or semiconductor) of the underlying substrate. Typically, the transfer is achieved by reactive ion etching or some other etching technique.
- the resist composition of the invention and resulting resist structures may be used to create patterned material layer structures such as metal wiring lines, holes for contacts or vias, insulation sections (e.g., damascene trenches or shallow trench isolation), trenches for capacitor structures, etc. as might be used in the design of integrated circuit devices.
- the processes for making these (ceramic, dielectric, metal or semiconductor) features generally involve providing a material layer or section of the substrate to be patterned, applying a layer of resist over the material layer or section, patternwise exposing the resist to radiation, developing the pattern by contacting the exposed resist with a developer, etching the layer(s) underlying the resist layer at spaces in the pattern whereby a patterned material layer or substrate section is formed, and removing any remaining resist from the substrate.
- a hard mask may be used below the resist layer to facilitate transfer of the pattern to a further underlying material layer or section. It should be understood that the invention is not limited to any specific lithography technique or device structure.
- Example 1 Synthesis of 2-trifluoromethanesulfonylaminoethyl methacrylate (I) To a solution of 15 g (0.091 mol) of 2-aminoethyl methacrylate hydrochloride (available from Aldrich) in 250 ml of anhydrous methylene chloride was added 18.4 g of redistilled triethylamine (0.182 mol). After the mixture was stirred at room temperature for 1 hour, 15.3 g trifluoromethane sulfonylchloride (0.091 mol) was added. The resulting mixture was further stirred at room temperature overnight. About 200 ml ether was added. The mixture was filtered to remove the precipitate formed.
- 2-aminoethyl methacrylate hydrochloride available from Aldrich
- the filtrate was sequentially washed with 2x100ml of 5% HCI, 100 ml of saturated NaHCO 3 , 2x100ml brine, and then dried over MgSO 4 .
- the solvents were removed by rotavap. About 14.5 g of viscous liquid was obtained.
- the product was further purified by recrystallization from 1 :1 hexane/chloroform to give about 12 g white solid (51%) having a melting point of 55-58 °C.
- Example 2 Synthesis of Poly(l-co-IV) 0.148 g (0.0009 mol) of 2,2'-azobisisobutyronitrile (AIBN) was added to a solution of 4.7 g (0.018 mol) of 2-trifluoromethanesulfonylaminoethyl methacrylate (I), 2.83 g (0.012 mol) of hydroxyadamantyl methacrylate (IV), and 0.061 g (0.0003 mol) dodecanethiol in 22.6 g of 2-butanone. The solution was deoxygenated by bubbling dry N 2 for 0.5 hr and then allowed to reflux for 12 hr.
- AIBN 2,2'-azobisisobutyronitrile
- reaction mixture was cooled to room temperature and precipitated in 400 ml of hexanes with rigorous stirring.
- the resulting white solid was collected by filtration, washed with several portions of hexanes and dried under vacuum at 60 °C for 20 hr.
- Example 3 Synthesis of Poly(l-co-IV-co-VI) The same procedure was used as in Example 2 with the following monomers: 2-trifluoromethanesulfonylaminoethyl methacrylate (I) (5.22 g, 0.02 mol), hydroxyadamantyl methacrylate (IV) (3.78 g, 0.016 mol), and 2-hydroxyethyl methacrylate (VI) (0.52 g, 0.004 mol), AIBN (0.197 g, 0.0012 mol), and dodecanethiol (0.081 g, 0.0004 mol).
- I 2-trifluoromethanesulfonylaminoethyl methacrylate
- IV hydroxyadamantyl methacrylate
- VI 2-hydroxyethyl methacrylate
- AIBN (0.197 g, 0.0012 mol
- dodecanethiol 0.081 g, 0.0004 mol
- Example 4 Synthesis of Poly(l-co-XVII-co-IV-co-VI) The same procedure was used as above in Example 2 with the following monomers: 2-trifluoromethanesulfonylaminoethyl methacrylate (I) (2.35 g, 0.009 mol), 2-methacryloyl- ⁇ -butyrolactone (XVII) (1.53 g, 0.009 mol), hydroxyadamantyl methacrylate (IV) (2.12 g, 0.009 mol), and 2-hydroxyethyl methacrylate (VI) (0.39 g, 0.003 mol), AIBN (0.246 g, 0.0015 mol), and dodecanethiol (0.182 g, 0.0009 mol).
- Example 5 Lithographic evaluation For the purpose of lithographic experiments, a resist formulation containing poly(l-co-XVII-co-IV-co-VI) (Example 4) was prepared by combining the following materials, expressed in part by weight:
- the resist formulation was spin-coated (for 30 seconds) onto an antireflective material layer (AR40, available from Shipley Company) applied on silicon wafers.
- the resist layer was soft-baked at 105 °C for 60 seconds on a vacuum hot plate to produce a film of about 0.24 ⁇ m thickness.
- the wafers were then exposed to 193 nm radiation (using ASML scanner, 0.75 NA).
- the exposure pattern was an array of lines and spaces of varying dimensions down to 0.08 ⁇ m.
- the exposed wafers were post-exposure baked on a vacuum hot plate at 105 °C for 90 seconds.
- the wafers were then (puddle) developed using 0.263 N TMAH developer for 60 seconds.
- the patterns were examined by scanning electron microscopy (SEM). Line/space pairs of 90 nm and above were well resolved.
- the negative resist compositions of the present invention are useful in the manufacture of patterned devices such as semiconductor chips and chip carriers.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006520525A JP4516963B2 (en) | 2003-09-16 | 2004-06-02 | Negative resist composition having fluorosulfonamide-containing polymer and pattern forming method |
EP04753854A EP1664923A4 (en) | 2003-09-16 | 2004-06-02 | Negative resist composition with fluorosulfonamide-containing polymer |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/663,553 | 2003-09-16 | ||
US10/663,553 US6949325B2 (en) | 2003-09-16 | 2003-09-16 | Negative resist composition with fluorosulfonamide-containing polymer |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005036261A1 true WO2005036261A1 (en) | 2005-04-21 |
Family
ID=34274407
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2004/017114 WO2005036261A1 (en) | 2003-09-16 | 2004-06-02 | Negative resist composition with fluorosulfonamide-containing polymer |
Country Status (6)
Country | Link |
---|---|
US (1) | US6949325B2 (en) |
EP (1) | EP1664923A4 (en) |
JP (1) | JP4516963B2 (en) |
KR (1) | KR100843804B1 (en) |
CN (1) | CN1846169A (en) |
WO (1) | WO2005036261A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007045787A (en) * | 2005-08-12 | 2007-02-22 | Central Glass Co Ltd | alpha-SUBSTITUTED ACRYLIC ACID NORBORNANYLS, METHOD FOR PRODUCING THE SAME AND COPOLYMER USING THE SAME |
US8956790B2 (en) | 2012-12-24 | 2015-02-17 | Cheil Industries Inc. | Positive photosensitive resin composition, and organic insulator film for display device and display device fabricated using the same |
Families Citing this family (74)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7063931B2 (en) * | 2004-01-08 | 2006-06-20 | International Business Machines Corporation | Positive photoresist composition with a polymer including a fluorosulfonamide group and process for its use |
US6991890B2 (en) * | 2004-02-06 | 2006-01-31 | International Business Machines Corporation | Negative photoresist composition involving non-crosslinking chemistry |
US7115771B2 (en) * | 2004-03-02 | 2006-10-03 | Central Glass Company, Limited | Process for producing fluorine-containing alkylsulfonylaminoethyl α-substituted acrylate |
JP4736474B2 (en) * | 2004-03-02 | 2011-07-27 | セントラル硝子株式会社 | Process for producing fluorine-containing alkylsulfonylaminoethyl α-substituted acrylates |
EP2468780B1 (en) * | 2004-09-30 | 2013-11-13 | JSR Corporation | Copolymer and top coating composition |
JP4583860B2 (en) * | 2004-10-04 | 2010-11-17 | 富士通株式会社 | Resist pattern thickening material, resist pattern forming method, semiconductor device and manufacturing method thereof |
KR20070116610A (en) * | 2005-02-22 | 2007-12-10 | 프로메러스, 엘엘씨 | Norbornene-type polymers, compositions thereof and lithographic processes using such compositions |
WO2006114958A1 (en) * | 2005-04-21 | 2006-11-02 | Asahi Glass Company, Limited | Photocurable composition, article with fine pattern and method for producing same |
US7375172B2 (en) * | 2005-07-06 | 2008-05-20 | International Business Machines Corporation | Underlayer compositions containing heterocyclic aromatic structures |
US7635551B2 (en) * | 2005-07-27 | 2009-12-22 | Sony Corporation | Poly (imide-azomethine) copolymer, poly (amic acid-azomethine) copolymer, and positive photosensitive resin composition |
JP2007047642A (en) * | 2005-08-12 | 2007-02-22 | Jsr Corp | Negative radiation-sensitive resin composition |
US20070231736A1 (en) * | 2006-03-28 | 2007-10-04 | Chen Kuang-Jung J | Bottom antireflective coating composition and method for use thereof |
US7435537B2 (en) * | 2006-06-21 | 2008-10-14 | International Business Machines Corporation | Fluorinated half ester of maleic anhydride polymers for dry 193 nm top antireflective coating application |
US7608390B2 (en) * | 2006-08-04 | 2009-10-27 | International Business Machines Corporation | Top antireflective coating composition containing hydrophobic and acidic groups |
JP5200464B2 (en) * | 2007-09-11 | 2013-06-05 | セントラル硝子株式会社 | Process for producing fluorine-containing alkylsulfonylaminoethyl α-substituted acrylates |
US7803521B2 (en) * | 2007-11-19 | 2010-09-28 | International Business Machines Corporation | Photoresist compositions and process for multiple exposures with multiple layer photoresist systems |
JP5002508B2 (en) * | 2008-03-27 | 2012-08-15 | 富士フイルム株式会社 | Negative resist composition and pattern forming method using the same |
JP2009244780A (en) * | 2008-03-31 | 2009-10-22 | Fujifilm Corp | Negative resist composition and resist pattern forming method |
KR101660041B1 (en) * | 2008-11-28 | 2016-09-26 | 도오꾜오까고오교 가부시끼가이샤 | Resist composition, method of forming resist pattern, novel compound, and acid generator |
JP5471382B2 (en) * | 2008-12-26 | 2014-04-16 | セントラル硝子株式会社 | Process for producing fluorine-containing alkylsulfonylaminoethyl α-substituted acrylates |
US8017303B2 (en) * | 2009-02-23 | 2011-09-13 | International Business Machines Corporation | Ultra low post exposure bake photoresist materials |
JP5544212B2 (en) * | 2009-04-27 | 2014-07-09 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, compound and method for producing the same, acid generator |
JP5469920B2 (en) * | 2009-05-29 | 2014-04-16 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP5401218B2 (en) * | 2009-09-03 | 2014-01-29 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP5439124B2 (en) * | 2009-11-11 | 2014-03-12 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
US9223209B2 (en) * | 2010-02-19 | 2015-12-29 | International Business Machines Corporation | Sulfonamide-containing photoresist compositions and methods of use |
US9223217B2 (en) * | 2010-02-19 | 2015-12-29 | International Business Machines Corporation | Sulfonamide-containing topcoat and photoresist additive compositions and methods of use |
JP5542500B2 (en) | 2010-03-30 | 2014-07-09 | 東京応化工業株式会社 | Resist pattern forming method and resist composition |
US8932795B2 (en) | 2010-05-19 | 2015-01-13 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern, novel compound, and acid generator |
JP5622448B2 (en) | 2010-06-15 | 2014-11-12 | 東京応化工業株式会社 | Resist composition, resist pattern formation method, polymer compound, compound |
JP5557657B2 (en) | 2010-09-02 | 2014-07-23 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, novel compound and acid generator |
JP5564402B2 (en) | 2010-10-29 | 2014-07-30 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, novel compound, acid generator |
JP5658546B2 (en) | 2010-11-30 | 2015-01-28 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, polymer compound |
JP5781755B2 (en) | 2010-12-08 | 2015-09-24 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP5749480B2 (en) | 2010-12-08 | 2015-07-15 | 東京応化工業株式会社 | New compounds |
JP5802385B2 (en) | 2010-12-08 | 2015-10-28 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP5690584B2 (en) | 2010-12-28 | 2015-03-25 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP5856809B2 (en) | 2011-01-26 | 2016-02-10 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP5677127B2 (en) | 2011-02-18 | 2015-02-25 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP5677135B2 (en) | 2011-02-23 | 2015-02-25 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, and polymer compound |
JP5723648B2 (en) | 2011-03-25 | 2015-05-27 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP5732306B2 (en) | 2011-04-20 | 2015-06-10 | 東京応化工業株式会社 | Compound, polymer compound, acid generator, resist composition, resist pattern forming method |
JP5758197B2 (en) | 2011-05-25 | 2015-08-05 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, novel compound, acid generator |
KR101884497B1 (en) | 2011-06-17 | 2018-08-01 | 도오꾜오까고오교 가부시끼가이샤 | Compound, radical polymerization initiator, method for producing compound, polymer, resist composition, and methiod for forming resist pattern |
US20120322006A1 (en) * | 2011-06-20 | 2012-12-20 | Central Glass Company, Limited | Fluorine-Containing Sulfonate Resin, Resist Composition and Pattern Formation Method |
US9057948B2 (en) | 2011-10-17 | 2015-06-16 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition for EUV or EB, and method of forming resist pattern |
JP2013097272A (en) | 2011-11-02 | 2013-05-20 | Tokyo Ohka Kogyo Co Ltd | Resist composition and method for forming resist pattern |
JP5856441B2 (en) | 2011-11-09 | 2016-02-09 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, and polymer compound |
JP5682542B2 (en) * | 2011-11-17 | 2015-03-11 | 信越化学工業株式会社 | Negative pattern forming method |
JP5764480B2 (en) | 2011-11-25 | 2015-08-19 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, and polymer compound |
JP5846888B2 (en) | 2011-12-14 | 2016-01-20 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP5846889B2 (en) | 2011-12-14 | 2016-01-20 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, compound |
JP2013142811A (en) | 2012-01-11 | 2013-07-22 | Tokyo Ohka Kogyo Co Ltd | Resist composition, method for forming resist pattern and novel compound |
JP2013171085A (en) | 2012-02-17 | 2013-09-02 | Tokyo Ohka Kogyo Co Ltd | Resist composition and method of forming resist pattern |
JP5978137B2 (en) | 2012-02-23 | 2016-08-24 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP5919148B2 (en) | 2012-03-28 | 2016-05-18 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, and polymer compound |
JP6002430B2 (en) | 2012-05-08 | 2016-10-05 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, compound |
JP6059517B2 (en) | 2012-05-16 | 2017-01-11 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP6130109B2 (en) | 2012-05-30 | 2017-05-17 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, compound |
JP6118533B2 (en) | 2012-06-13 | 2017-04-19 | 東京応化工業株式会社 | Compound, resist composition, resist pattern forming method. |
JP6006999B2 (en) | 2012-06-20 | 2016-10-12 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP6037689B2 (en) | 2012-07-10 | 2016-12-07 | 東京応化工業株式会社 | Method for producing ammonium salt compound and method for producing acid generator |
JP6097610B2 (en) | 2013-03-25 | 2017-03-15 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP6097611B2 (en) | 2013-03-25 | 2017-03-15 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP6093614B2 (en) | 2013-03-25 | 2017-03-08 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
JP6249664B2 (en) | 2013-07-31 | 2017-12-20 | 東京応化工業株式会社 | Resist composition, acid generator, and resist pattern forming method |
JP6307250B2 (en) | 2013-11-15 | 2018-04-04 | 東京応化工業株式会社 | Resist composition, resist pattern formation method, polymer compound, compound |
JP6322424B2 (en) | 2014-01-16 | 2018-05-09 | 東京応化工業株式会社 | Resist composition, resist pattern forming method, and polymer compound |
JP6397696B2 (en) | 2014-08-26 | 2018-09-26 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
TWI672562B (en) * | 2015-09-30 | 2019-09-21 | 南韓商羅門哈斯電子材料韓國公司 | Photoresist compositions and methods |
JP6706530B2 (en) | 2016-03-31 | 2020-06-10 | 東京応化工業株式会社 | Resist composition and method for forming resist pattern |
DE112017002428T5 (en) * | 2016-05-12 | 2019-01-31 | Quingzhou Cui | POLYSULFONAMIDE REDISTRIBUTION COMPOSITIONS AND METHOD FOR THEIR USE |
EP3974047A4 (en) | 2019-05-22 | 2023-06-07 | Tokyo Ohka Kogyo Co., Ltd. | Production method for resist composition purified product, resist pattern-forming method, and resist composition purified product |
JP7394591B2 (en) | 2019-11-14 | 2023-12-08 | 東京応化工業株式会社 | Resist composition and resist pattern forming method |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6177228B1 (en) * | 1997-09-12 | 2001-01-23 | International Business Machines Corporation | Photoresist composition and process for its use |
US6420503B1 (en) * | 1999-02-05 | 2002-07-16 | Sumitomo Bakelite Co. Ltd. | Norbornene sulfonamide polymers |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6291129B1 (en) | 1997-08-29 | 2001-09-18 | Kabushiki Kaisha Toshiba | Monomer, high molecular compound and photosensitive composition |
US6165678A (en) | 1997-09-12 | 2000-12-26 | International Business Machines Corporation | Lithographic photoresist composition and process for its use in the manufacture of integrated circuits |
EP1046958B1 (en) | 1998-07-10 | 2006-04-12 | AZ Electronic Materials USA Corp. | Use of a composition for bottom reflection preventive film |
US6187505B1 (en) | 1999-02-02 | 2001-02-13 | International Business Machines Corporation | Radiation sensitive silicon-containing resists |
US6235849B1 (en) | 1999-02-05 | 2001-05-22 | The B. F. Goodrich Company | Method of preparing norbornene sulfonamide polymers |
EP1246856B1 (en) * | 1999-10-27 | 2009-07-15 | 3M Innovative Properties Company | Fluorochemical sulfonamide surfactants |
US6764809B2 (en) * | 2000-10-12 | 2004-07-20 | North Carolina State University | CO2-processes photoresists, polymers, and photoactive compounds for microlithography |
US6653045B2 (en) | 2001-02-16 | 2003-11-25 | International Business Machines Corporation | Radiation sensitive silicon-containing negative resists and use thereof |
JP4645789B2 (en) * | 2001-06-18 | 2011-03-09 | Jsr株式会社 | Negative radiation sensitive resin composition |
JP3877605B2 (en) * | 2002-02-08 | 2007-02-07 | 信越化学工業株式会社 | Negative resist material and pattern forming method using the same |
JP4054237B2 (en) * | 2002-09-10 | 2008-02-27 | 富士フイルム株式会社 | Master for lithographic printing plate |
US7189490B2 (en) * | 2002-10-21 | 2007-03-13 | Shipley Company, L.L.C. | Photoresists containing sulfonamide component |
-
2003
- 2003-09-16 US US10/663,553 patent/US6949325B2/en not_active Expired - Fee Related
-
2004
- 2004-06-02 EP EP04753854A patent/EP1664923A4/en not_active Withdrawn
- 2004-06-02 JP JP2006520525A patent/JP4516963B2/en not_active Expired - Fee Related
- 2004-06-02 CN CNA2004800254892A patent/CN1846169A/en active Pending
- 2004-06-02 WO PCT/US2004/017114 patent/WO2005036261A1/en not_active Application Discontinuation
- 2004-06-02 KR KR1020067003191A patent/KR100843804B1/en not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6177228B1 (en) * | 1997-09-12 | 2001-01-23 | International Business Machines Corporation | Photoresist composition and process for its use |
US6420503B1 (en) * | 1999-02-05 | 2002-07-16 | Sumitomo Bakelite Co. Ltd. | Norbornene sulfonamide polymers |
Non-Patent Citations (1)
Title |
---|
See also references of EP1664923A4 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007045787A (en) * | 2005-08-12 | 2007-02-22 | Central Glass Co Ltd | alpha-SUBSTITUTED ACRYLIC ACID NORBORNANYLS, METHOD FOR PRODUCING THE SAME AND COPOLYMER USING THE SAME |
US8956790B2 (en) | 2012-12-24 | 2015-02-17 | Cheil Industries Inc. | Positive photosensitive resin composition, and organic insulator film for display device and display device fabricated using the same |
Also Published As
Publication number | Publication date |
---|---|
US20050058930A1 (en) | 2005-03-17 |
EP1664923A4 (en) | 2008-08-27 |
CN1846169A (en) | 2006-10-11 |
JP4516963B2 (en) | 2010-08-04 |
EP1664923A1 (en) | 2006-06-07 |
US6949325B2 (en) | 2005-09-27 |
KR100843804B1 (en) | 2008-07-03 |
JP2007525696A (en) | 2007-09-06 |
KR20060081403A (en) | 2006-07-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6949325B2 (en) | Negative resist composition with fluorosulfonamide-containing polymer | |
JP4156599B2 (en) | Positive photoresist composition comprising a polymer containing fluorosulfonamide groups and method of use thereof | |
TWI400569B (en) | Positive photosensitive composition and pattern forming method using the same | |
KR102262814B1 (en) | Photoresists comprising carbamate component | |
KR19990044985A (en) | Novel polymer and photosensitive resist composition | |
JPH11119434A (en) | Resist material and resist pattern forming method | |
JPH10161313A (en) | Resist material and resist pattern forming method | |
TWI396943B (en) | Positive resist composition and pattern forming method using the same | |
JP2008083159A (en) | Positive photosensitive composition and pattern forming method using the same | |
JP2003233190A (en) | Polymer with mixed photoacid-labile group and photoresist comprising the same | |
US20040072095A1 (en) | Photoresist compositions | |
JP5520489B2 (en) | Lithographic substrate coating method and actinic ray-sensitive or radiation-sensitive resin composition used in the method | |
WO2004029719A1 (en) | 193nm resist | |
JP2008083157A (en) | Positive photosensitive composition and pattern forming method using the same | |
IL167255A (en) | Low silicon-outgassing resist for bilayer lithography | |
JP4951464B2 (en) | A positive resist composition and a pattern forming method using the same. | |
JP4667278B2 (en) | Positive photosensitive composition and pattern forming method using the same | |
JP2007240631A (en) | Positive resist composition and pattern forming method using the same | |
CN114442427A (en) | Photoresist composition and pattern forming method | |
JP4512340B2 (en) | Positive resist composition and pattern forming method using the same | |
JP4682073B2 (en) | Positive photosensitive composition and pattern forming method using the same | |
US7081326B2 (en) | Negative photoresist and method of using thereof | |
JP2004126509A (en) | Solvent and photoresist composition for 193nm imaging |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200480025489.2 Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1020067003191 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2006520525 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004753854 Country of ref document: EP |
|
DPEN | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed from 20040101) | ||
WWP | Wipo information: published in national office |
Ref document number: 2004753854 Country of ref document: EP |
|
NENP | Non-entry into the national phase |
Ref country code: JP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: JP |