WO2009096340A1 - 硫黄原子を含有するレジスト下層膜形成用組成物及びレジストパターンの形成方法 - Google Patents
硫黄原子を含有するレジスト下層膜形成用組成物及びレジストパターンの形成方法 Download PDFInfo
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- WO2009096340A1 WO2009096340A1 PCT/JP2009/051109 JP2009051109W WO2009096340A1 WO 2009096340 A1 WO2009096340 A1 WO 2009096340A1 JP 2009051109 W JP2009051109 W JP 2009051109W WO 2009096340 A1 WO2009096340 A1 WO 2009096340A1
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/423—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof containing an atom other than oxygen belonging to a functional groups to C08G59/42, carbon and hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
- C08G59/186—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents with acids
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
- H01L21/0275—Photolithographic processes using lasers
Definitions
- the present invention relates to a composition for forming a resist underlayer film provided between a substrate and a resist film (resist layer) formed thereon suitable for a lithography process using an immersion exposure apparatus.
- the resist underlayer film suppresses the influence of the reflected wave on the resist film when exposing the resist film
- the resist underlayer film can be referred to as an antireflection film.
- Patent Document 1 An antireflection film-forming composition containing a polymer containing sulfur atoms in a predetermined ratio is disclosed in Patent Document 1 below.
- the conventional antireflective film-forming composition containing a polymer containing a sulfur atom sometimes has a problem of odor when the polymer is synthesized.
- a typical example in which odor is a problem is a case where a compound having a thiol group (—SH) is used as a raw material monomer for a polymer containing a sulfur atom.
- —SH thiol group
- the resist underlayer film can be easily formed by applying and curing a solution-like composition for forming a resist underlayer film. Therefore, the composition needs to contain a compound (polymer) that is easily cured by heating or the like and highly soluble in a predetermined solvent. When synthesizing such a compound (polymer) and when using a reaction product, it is not preferable for workers, operators, etc. to generate malodor.
- the resist pattern formed on the resist underlayer film has a substantially rectangular cross-sectional shape in the direction perpendicular to the substrate (a straight skirt shape without so-called undercut or skirting).
- a straight skirt shape without so-called undercut or skirting.
- the resist lower layer film is required to have a higher dry etching rate than the upper layer resist film, that is, to have a higher selection ratio of the dry etching rate.
- naphthalene can lower the k value at a wavelength of 193 nm, but a resist underlayer film having a low k value at a wavelength of 193 nm has a problem that the refractive index (n value) at the same wavelength also decreases.
- the present invention forms a resist underlayer film having a high selectivity to a resist film at a dry etching rate, a low k value at a short wavelength, and a high n value, such as an ArF excimer laser (wavelength of about 193 nm). It aims at providing the composition for. It is another object of the present invention to provide a composition for forming a resist underlayer film in which a resist pattern formed on the resist underlayer film has a desired shape as described above. Furthermore, it aims at providing the composition for forming the resist underlayer film from which the odor resulting from the raw material monomer at the time of the synthesis
- the first aspect of the present invention is a resist underlayer film forming composition for lithography comprising a polymer having a disulfide bond, that is, an “SS bond” in the main chain, and a solvent.
- the meaning of the polymer is a polymer and is not necessarily limited to the polymer compound, and therefore the monomer is excluded but the oligomer is not excluded.
- the polymer is a reaction product of at least one compound containing two epoxy groups (hereinafter referred to as Compound A) and at least one dicarboxylic acid salt containing a disulfide bond (hereinafter referred to as Compound B). . That is, it can be obtained by dissolving compound A and compound B in a solvent in an appropriate molar ratio and polymerizing them in the presence of a catalyst that activates an epoxy group.
- a compound containing two epoxy groups is also expressed as a diepoxy compound.
- the catalyst for activating the epoxy group is, for example, a quaternary phosphonium salt such as triphenylmonoethylphosphonium bromide or a quaternary ammonium salt such as benzyltriethylammonium chloride.
- An appropriate amount can be selected and used from the range of 0.1% by mass to 10% by mass with respect to the total mass of B.
- Optimum conditions for the temperature and time for the polymerization reaction are selected from the range of 80 ° C. to 160 ° C. and 2 hours to 50 hours.
- dicarboxylic acid means a compound having two carboxyl groups.
- compound B can be rephrased as at least one compound containing a disulfide bond and two carboxyl groups. And since compound B contains two carboxyl groups, it is not necessary to contain a thiol group.
- R 0 represents an alkylene group having 2 to 6 carbon atoms.
- the polymer contained in the resist underlayer film forming composition of the first aspect of the present invention is, for example, the following formula (1):
- X represents the following formula (2), formula (3) or formula (4):
- R 1 to R 5 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a benzyl group or a phenyl group, , At least one group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a cyano group, and an alkylthio group having 1 to 6 carbon atoms.
- R 1 and R 2 , R 3 and R 4 may be bonded to each other to form a ring having 3 to 6 carbon atoms.
- 1 to A 6 each independently represents a hydrogen atom, a methyl group or an ethyl group
- Q 1 represents a divalent group containing a disulfide bond
- n is the number of repeating unit structures, and an integer of 5 to 100 Represents. ] It has the repeating unit structure represented by these.
- the formula (1) is, for example, the following formula (5): [In the above formula, X represents a group represented by the above formula (2), formula (3) or formula (4), and R 6 and R 7 are each independently an alkylene group having 1 to 3 carbon atoms or a direct group. Represents a bond, and p represents the number of repeating unit structures and represents an integer of 5 to 100. ] Is represented.
- the second aspect of the present invention is the following formula (1 ′):
- X represents the following formula (2), formula (3) or formula (4):
- R 1 to R 5 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a benzyl group or a phenyl group, , At least one group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a cyano group, and an alkylthio group having 1 to 6 carbon atoms.
- R 1 and R 2 , R 3 and R 4 may be bonded to each other to form a ring having 3 to 6 carbon atoms.
- 1 to A 6 each independently represents a hydrogen atom, a methyl group or an ethyl group
- Q 2 represents a divalent group having a sulfur atom
- q is the number of repeating unit structures, and is an integer of 5 to 100 Represents.
- the resist underlayer film forming composition for lithography containing the polymer which has a repeating unit structure represented by these, and a solvent.
- the meaning of the polymer is a polymer that is not necessarily limited to the polymer compound, and thus the monomer is excluded but the oligomer is not excluded.
- the number of sulfur atoms contained in the divalent group represented by Q 2 is not limited, but may be one or two, for example.
- the polymer is a reaction product of at least one diepoxy compound and at least one dicarboxylic acid having a sulfur atom. That is, it is obtained by dissolving the diepoxy compound and dicarboxylic acid, which are raw material monomers, in a solvent in an appropriate molar ratio and polymerizing in the presence of a catalyst that activates the epoxy group.
- the catalyst for activating the epoxy group is, for example, a quaternary phosphonium salt such as triphenylmonoethylphosphonium bromide or a quaternary ammonium salt such as benzyltriethylammonium chloride.
- An appropriate amount can be selected from the range of 0.1% by mass to 10% by mass with respect to the total mass of the acid.
- Optimum conditions for the temperature and time for the polymerization reaction are selected from the range of 80 ° C. to 160 ° C. and 2 hours to 50 hours.
- the diepoxy compound means a compound having two epoxy groups
- the dicarboxylic acid means a compound having two carboxyl groups.
- a raw material monomer does not contain a thiol group.
- dicarboxylic acid which has a sulfur atom is illustrated to the following formula
- diepoxy compounds have already been shown herein as formulas (a) to (h).
- the formula (1 ′) is, for example, the following formula (6):
- X represents a group represented by the above formula (2), formula (3) or formula (4), and R 6 and R 7 are each independently an alkylene group having 1 to 3 carbon atoms or a direct group.
- R 8 represents an alkylene group having 1 to 3 carbon atoms, m represents 0 or 1, r represents the number of repeating unit structures, and represents an integer of 5 to 100.
- the resist underlayer film forming composition according to the first and second aspects of the present invention can be applied to a lithography process in the process of manufacturing a semiconductor device.
- the lithography step includes applying a resist underlayer film forming composition according to the first and second aspects of the present invention on a semiconductor substrate and baking the resist underlayer film, and applying a resist on the resist underlayer film. And bake to form a resist film, to expose the resist underlayer film and the semiconductor substrate coated with the resist film, and to develop the resist film after the exposure, the resist underlayer film A resist pattern is formed thereon.
- the semiconductor substrate is typically a silicon wafer, but an SOI (Silicon on Insulator) substrate or a compound semiconductor wafer such as gallium arsenide (GaAs), indium phosphide (InP), or gallium phosphide (GaP) is used. It may be used.
- a semiconductor substrate on which an insulating film such as a silicon oxide film, a nitrogen-containing silicon oxide film (SiON film), or a carbon-containing silicon oxide film (SiOC film) is formed may be used. In that case, a resist underlayer film is formed on the insulating film. Apply the forming composition.
- an ArF excimer laser can be used as a light source.
- EUV wavelength 13.5 nm
- electron beam may be used.
- EUV is an abbreviation for extreme ultraviolet light.
- the resist for forming the resist film may be either a positive type or a negative type.
- a chemically amplified resist that is sensitive to ArF excimer laser, EUV, or electron beam can be used.
- the resist underlayer film forming composition of the present invention is a polymer having a disulfide bond in the main chain, which can efficiently introduce a sulfur atom having a high n value and a low k value at a wavelength of 193 nm, or the above formula (1 ′) And a polymer having a repeating unit structure represented by the formula (1), wherein the odor caused by the raw material monomer is small enough not to cause a problem.
- the resist underlayer film formed from such a composition has a high antireflection effect and is adjusted to a suitable value in a lithography process using an immersion exposure apparatus and using irradiation light with a short wavelength such as an ArF excimer laser. The obtained k value is obtained.
- a resist pattern having a good shape can be formed on the resist underlayer film without causing intermixing with the resist film. Further, the resist underlayer film can be removed in a much shorter time than the resist pattern by dry etching with a gas such as CF 4 or CHF 3 .
- the solvent contained in the resist underlayer film forming composition of the present invention include propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monopropyl ether, methyl ethyl ketone, ethyl lactate, cyclohexanone, ⁇ - Examples include butyrolactone, N-methylpyrrolidone, and a mixture of two or more selected from these solvents.
- the ratio of the solvent with respect to the resist underlayer film forming composition of this invention is 90 to 99.9 mass%, for example.
- the resist underlayer film forming composition of the present invention can further contain a crosslinkable compound and a sulfonic acid compound.
- the ratio of the sulfonic acid compound to the polymer contained in the resist underlayer film forming composition of the present invention is, for example, from 0.1% by mass to 13% by mass, and preferably from 0.5% by mass to 5% by mass.
- the crosslinkable compound is also expressed as a crosslinking agent, and is, for example, a nitrogen-containing compound having 2 to 4 nitrogen atoms substituted with a methylol group or an alkoxymethyl group.
- the ratio of the crosslinkable compound to the polymer contained in the resist underlayer film forming composition of the present invention is, for example, 5% by mass or more and 50% by mass or less.
- the sulfonic acid compound examples include p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium-p-toluenesulfonic acid, camphorsulfonic acid, 5-sulfosalicylic acid, 4-chlorobenzenesulfonic acid, 4-hydroxybenzenesulfonic acid, Examples thereof include benzene disulfonic acid, 1-naphthalene sulfonic acid, pyridinium-1-naphthalene sulfonic acid, and the like.
- crosslinkable compound crosslinking agent
- crosslinking agent examples include hexamethoxymethylmelamine, tetramethoxymethylbenzoguanamine, 1,3,4,6-tetrakis (methoxymethyl) glycoluril, 1,3,4,6-tetrakis (butoxy).
- the sulfonic acid compound acts as a crosslinking accelerator, and, for example, 4-hydroxybenzenesulfonic acid (also referred to as p-phenolsulfonic acid) suppresses the resist pattern cross section perpendicular to the substrate from becoming a footing shape, It is an additive that contributes to a desired shape (generally rectangular shape).
- the resist underlayer film forming composition of the present invention may contain a phenol derivative. Similar to 4-hydroxybenzenesulfonic acid, the phenol derivative is an additive that suppresses the cross section of the resist pattern perpendicular to the substrate from becoming a footing shape and contributes to a desired shape (generally rectangular shape). . Specific examples of phenol derivatives include 4-methylsulfonylphenol, bisphenol S, bisphenol AF, 4-cyanophenol, 3,4,5-trifluorophenol, 4-hydroxybenzotrifluoride, 2,3,5,6-tetra Examples thereof include fluoro-4- (trifluoromethyl) phenol and 2,6-dichloro-4- (methylsulfonyl) phenol. The ratio of the phenol derivative to the polymer contained in the resist underlayer film forming composition of the present invention is, for example, 0.1% by mass or more and 20% by mass or less.
- the resist underlayer film forming composition of the present invention may contain a surfactant.
- the surfactant is an additive for improving applicability to the substrate.
- Known surfactants such as nonionic surfactants and fluorine-based surfactants can be used.
- the solid content includes a polymer and various additives as described above that are added as necessary.
- the weight average molecular weight shown in the following synthesis examples of this specification is a measurement result by gel permeation chromatography (hereinafter abbreviated as GPC).
- the measurement conditions etc. are as follows using the Tosoh Co., Ltd. product GPC apparatus for a measurement.
- GPC column Shodex (registered trademark) and Asahipak (registered trademark) (Showa Denko KK) Column temperature: 40 ° C Solvent: N, N-dimethylformamide (DMF) Flow rate: 0.6ml / min Standard sample: Polystyrene (Tosoh Corporation)
- the odor of the raw material compound and the odor of the reaction product are at a level that is hardly noticed.
- the weight average molecular weight was about 7800 in standard polystyrene conversion.
- This reaction product has a repeating unit structure represented by the following formula (7).
- ethanedithiol felt a strong odor compared to the sulfur-containing compounds used in other synthesis examples of the present specification.
- the cause of bad odor is because ethanedithiol has a thiol group.
- the weight average molecular weight was about 16800 in standard polystyrene conversion.
- This reaction product has a repeating unit structure not containing a disulfide bond (SS bond) represented by the following formula (9).
- Example 1 To 1.594 g of the solution containing 0.234 g of the reaction product obtained in Synthesis Example 1, 19.56 g of propylene glycol monomethyl ether, 8.910 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries Co., Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.059 g, p-phenolsulfonic acid (Tokyo Chemical Industry Co., Ltd.) 0.006 g, and surfactant (Dainippon Ink Chemical Co., Ltd., trade name: R) -30) 0.001 g was added to make a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 2 To 1.353 g of the solution containing 0.217 g of the reaction product obtained in Synthesis Example 1, 19.655 g of propylene glycol monomethyl ether, 8.910 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries Co., Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.054 g, p-phenolsulfonic acid (Tokyo Chemical Industry Co., Ltd.) 0.027 g, and surfactant (Dainippon Ink Chemical Co., Ltd., trade name: R) -30) 0.001 g was added to make a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 3 To 1.391 g of a solution containing 0.223 g of the reaction product obtained in Synthesis Example 1, 19.623 g of propylene glycol monomethyl ether, 8.910 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries, Ltd., Trade name: POWDERLINK (registered trademark) 1174) 0.056 g, 4-methylsulfonylphenol (Acros Organics) 0.014 g, p-phenolsulfonic acid (Tokyo Chemical Industry Co., Ltd.) 0.006 g, and a surfactant ( Dainippon Ink & Chemicals, Inc., trade name: R-30) 0.001 g was added to make a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 4 To 1.504 g of the solution containing 0.233 g of the reaction product obtained in Synthesis Example 1, 25.460 g of propylene glycol monomethyl ether, 2.970 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries, Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.058 g, 4-methylsulfonylphenol (Acros Organics) 0.002 g, p-phenolsulfonic acid (Tokyo Chemical Industry Co., Ltd.) 0.006 g, and surfactant (Dainippon Ink Chemical Co., Ltd., trade name: R-30) 0.005 g was added to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 5 To 1.391 g of the solution containing 0.223 g of the reaction product obtained in Synthesis Example 1, 19.623 g of propylene glycol monomethyl ether, 8.910 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries, Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.056 g, bisphenol S (Tokyo Chemical Industry Co., Ltd.) 0.014 g, p-phenolsulfonic acid (Tokyo Chemical Industry Co., Ltd.) 0.006 g, and surfactant (Dainippon Ink Chemical Co., Ltd., trade name: R-30) 0.005 g was added to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 6 To 1.391 g of the solution containing 0.223 g of the reaction product obtained in Synthesis Example 1, 19.623 g of propylene glycol monomethyl ether, 8.910 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries, Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.056 g, bisphenol AF (Tokyo Chemical Industry Co., Ltd.) 0.014 g, p-phenolsulfonic acid (Tokyo Chemical Industry Co., Ltd.) 0.006 g, and surfactant (Dainippon Ink Chemical Co., Ltd., trade name: R-30) 0.005 g was added to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 7 To 1.391 g of the solution containing 0.223 g of the reaction product obtained in Synthesis Example 1, 19.623 g of propylene glycol monomethyl ether, 8.910 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries, Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.056 g, 4-cyanophenol (Tokyo Chemical Industry Co., Ltd.) 0.014 g, p-phenolsulfonic acid (Tokyo Chemical Industry Co., Ltd.) 0.006 g, and interface 0.001 g of an activator (Dainippon Ink Chemical Co., Ltd., trade name: R-30) was added to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 8 To 1.391 g of the solution containing 0.223 g of the reaction product obtained in Synthesis Example 1, 19.623 g of propylene glycol monomethyl ether, 8.910 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries, Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.056 g, 3,4,5-trifluorophenol (Tokyo Chemical Industry Co., Ltd.) 0.014 g, p-phenolsulfonic acid (Tokyo Chemical Industry Co., Ltd.) 0 .006 g and 0.005 g of a surfactant (Dainippon Ink Chemical Co., Ltd., trade name: R-30) were added to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 9 To 1.412 g of the solution containing 0.234 g of the reaction product obtained in Synthesis Example 2, 27.038 g of propylene glycol monomethyl ether, 1.485 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries Co., Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.059 g, 5-sulfosalicylic acid (Tokyo Kasei Kogyo Co., Ltd.) 0.006 g, and surfactant (Dainippon Ink Chemical Co., Ltd., trade name: R- 30) 0.001g was added and it was set as the solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 10 To 1.412 g of the solution containing 0.234 g of the reaction product obtained in Synthesis Example 2, 27.038 g of propylene glycol monomethyl ether, 1.485 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries Co., Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.059 g, p-phenolsulfonic acid (Tokyo Chemical Industry Co., Ltd.) 0.006 g, and surfactant (Dainippon Ink Chemical Co., Ltd., trade name: R) -30) 0.001 g was added to make a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 11 To 3.433 g of a solution containing 0.927 g of the reaction product obtained in Synthesis Example 5, 23.4 g of propylene glycol monomethyl ether, 2.88 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (manufactured by Nippon Cytec Industries Co., Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.23 g, p-phenolsulfonic acid 0.023 g, surfactant (Dainippon Ink Chemical Co., Ltd., trade name: R-30) 0.018 g, It was set as the solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 12 To 3.275 g of the solution containing 0.884 g of the reaction product obtained in Synthesis Example 5, 23.5 g of propylene glycol monomethyl ether, 2.88 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (manufactured by Nippon Cytec Industries Co., Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.22 g, bisphenol S (Tokyo Chemical Industry Co., Ltd.) 0.055 g, p-phenolsulfonic acid 0.022 g, surfactant (Dainippon Ink & Chemicals, Inc.) , Trade name: R-30) 0.018 g was added to give a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 13 To 3.358 g of the solution containing 0.927 g of the reaction product obtained in Synthesis Example 6, 23.5 g of propylene glycol monomethyl ether, 2.88 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (manufactured by Nippon Cytec Industries, Ltd.) , Trade name: POWDERLINK (registered trademark) 1174) 0.23 g, p-phenolsulfonic acid 0.023 g, surfactant (Dainippon Ink Chemical Co., Ltd., trade name: R-30) 0.018 g was added. A solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 14 To 3.204 g of the solution containing 0.884 g of the reaction product obtained in Synthesis Example 6, 23.6 g of propylene glycol monomethyl ether, 2.88 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries, Ltd., Product name: POWDERLINK (registered trademark) 1174) 0.22 g, bisphenol S (Tokyo Chemical Industry Co., Ltd.) 0.055 g, p-phenolsulfonic acid 0.022 g, surfactant (Dainippon Ink Chemical Co., Ltd.), (Product name: R-30) 0.018 g was added to prepare a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 15 To 1.293 g of a solution containing 0.235 g of the reaction product obtained in Synthesis Example 7, 19.7 g of propylene glycol monomethyl ether, 8.91 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (Nippon Cytec Industries, Ltd., Trade name: POWDERLINK (registered trademark) 1174) 0.059 g and pyridinium-p-toluenesulfonate 0.006 g were added to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- Example 16 To 1.265 g of the solution containing 0.235 g of the reaction product obtained in Synthesis Example 8, 19.76 g of propylene glycol monomethyl ether, 8.91 g of propylene glycol monomethyl ether acetate, tetramethoxymethyl glycoluril (manufactured by Nippon Cytec Industries Co., Ltd.) (Trade name: POWDERLINK (registered trademark) 1174) and 0.056 g of pyridinium-p-toluenesulfonate were added to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and prepared the composition for resist underlayer film formation.
- POWDERLINK registered trademark
- a photoresist solution (manufactured by Sumitomo Chemical Co., Ltd., trade name: PAR710) was applied onto a silicon wafer by a spinner and baked on a hot plate at 90 ° C. for 1 minute to form a photoresist film.
- the dry etching rate was measured using RIE system ES401 manufactured by Nippon Scientific Co., Ltd. under the condition that CF 4 was used as the dry etching gas.
- the resist underlayer film obtained from the resist underlayer film forming composition of the present invention has sufficiently high n value and low k value for light having a wavelength of 193 nm. . Furthermore, it can be seen that the resist underlayer film obtained from the composition for forming a resist underlayer film of the present invention has a higher dry etching rate selectivity than a photoresist. Therefore, the time required for removing the resist underlayer film by dry etching can be shortened, and an undesirable phenomenon in which the film thickness of the photoresist film is reduced due to the removal of the resist underlayer film by dry etching can be suppressed.
- the resist underlayer film obtained from the resist underlayer film forming composition prepared in Comparative Example 1 has a k value larger than any resist underlayer film obtained from the resist underlayer film forming composition of the present invention.
- the resist underlayer film obtained from the resist underlayer film forming composition prepared in Comparative Example 2 has a higher dry etching rate selection than any resist underlayer film obtained from the resist underlayer film forming composition of the present invention. The ratio is small. Furthermore, in the composition for forming a resist underlayer film prepared in Comparative Example 1, a bad odor attributed to a raw material monomer that is not a problem in the composition for forming a resist underlayer film of the present invention is felt.
- composition for forming a resist underlayer film prepared in each example described in this specification is applied to an insulating film such as a SiON film (nitrogen-containing silicon oxide film) or low-k (low dielectric constant) on a silicon wafer by a spinner.
- the film is applied onto a substrate having a thickness of, for example, 0.05 ⁇ m.
- baking is performed on a hot plate (for example, at 205 ° C. for 1 minute) to form a resist underlayer film having a thickness of 20 nm to 30 nm.
- a commercially available photoresist solution for example, product name: PAR855S75 manufactured by Sumitomo Chemical Co., Ltd.
- a spinner for example, product name: PAR855S75 manufactured by Sumitomo Chemical Co., Ltd.
- a hot plate for example, 115 ° C. for 1 minute
- a scanner for example, NSRS307E (wavelength 193 nm, NA: 0.85, ⁇ : 0.65 / 0.93 (ANNNULAR)) manufactured by Nikon Corporation, the line width of the photoresist and the photoresist The width between the lines is 0.08 ⁇ m, that is, 0.08 ⁇ mL / S (dense line), and exposure is performed through a photomask set so that nine such lines are formed.
- PEB heating after exposure
- a 0.26N aqueous tetramethylammonium hydroxide solution is used as a developer in an industrial standard 60-second single paddle process Develop using.
- the composition for forming a resist underlayer film prepared in Examples 1, 2, 4 to 8 described in the present specification is obtained by using a spinner to form a SiON film (nitrogen-containing silicon oxide film) having a thickness of 0.05 ⁇ m on a silicon wafer. Then, it was coated on the substrate deposited. Then, baking was performed at 205 ° C. for 1 minute on a hot plate to form a resist underlayer film having a thickness of 20 nm to 30 nm.
- NSRS307E wavelength: 193 nm, NA: 0.85, ⁇ : 0.65 / 0.93 (ANNNULAR)
- the width of the film was 0.08 ⁇ m, that is, 0.08 ⁇ mL / S (dense line)
- exposure was performed through a photomask set so that nine such lines were formed.
- PEB exposure
- a 0.26N aqueous tetramethylammonium hydroxide solution is used as a developer in an industrial standard 60-second single paddle process. And developed.
- the cross section in the direction perpendicular to the substrate, that is, the silicon wafer was observed with a scanning electron microscope (SEM).
- SEM scanning electron microscope
- (A) is the SEM image which image
- (B) is the resist underlayer film of Example 4. It is the SEM image which image
- (C) uses the resist underlayer film forming composition of Example 5, and is finally on a board
- (E) is an SEM image obtained by photographing the cross section of the photoresist pattern finally formed on the substrate using the resist underlayer film forming composition of Example 8.
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Abstract
Description
で表される繰り返し単位構造を有する。
GPCカラム:Shodex〔登録商標〕・Asahipak〔登録商標〕(昭和電工(株))
カラム温度:40℃
溶媒:N,N-ジメチルホルムアミド(DMF)
流量:0.6ml/min
標準試料:ポリスチレン(東ソー(株))
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)、商品名:MADGIC)5.0g、3,3’-ジチオジプロピオン酸(堺化学工業(株)、商品名:DTDPA)3.8g、及び触媒として第4級ホスホニウム塩であるトリフェニルモノエチルホスホニウムブロミド0.3gを、プロピレングリコールモノメチルエーテル13.8gに溶解させた後、120℃に加温し、窒素雰囲気下で4時間撹拌した。原料化合物の臭い及び反応生成物の臭いは、ほとんど気にならないレベルである。得られた反応生成物を、プロピレングリコールモノメチルエーテル23.0gにて希釈したワニス溶液のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は約7800であった。この反応生成物は、下記式(7)で表される繰り返し単位構造を有する。
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)、商品名:MADGIC)14.0g、モノアリルイソシアヌル酸(四国化成工業(株))2.6g、3,3’-ジチオジプロピオン酸(堺化学工業(株)製、商品名:DTDPA)7.4g、及び触媒として第4級アンモニウム塩であるベンジルトリエチルアンモニウムクロリド0.6gをプロピレングリコールモノメチルエーテル57.3gに溶解させた後、120℃に加温し、窒素雰囲気下で4時間撹拌した。原料化合物の臭い及び反応生成物の臭いは、ほとんど気にならないレベルである。得られた反応生成物をプロピレングリコールモノメチルエーテル40.9gにて希釈したワニス溶液のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は約8800であった。この反応生成物は、下記式(8)で表される繰り返し単位構造を有する。
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)、商品名:MADGIC)10.00g、エタンジチオール(四国化成工業(株))4.98g、及び触媒として第4級アンモニウム塩であるベンジルトリエチルアンモニウムクロリド0.40gを、プロピレングリコールモノメチルエーテル61.52gに溶解し、還流下24時間反応させた。原料化合物(モノマー)のうち特にエタンジチオールは、本明細書の他の合成例で使用する含硫黄化合物と比較して強い悪臭が感じられた。悪臭の原因は、エタンジチオールがチオール基を有するためである。得られた反応生成物を含むワニス溶液のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は約16800であった。この反応生成物は、下記式(9)で表される、ジスルフィド結合(S-S結合)を含有しない繰り返し単位構造を有する。
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)、商品名:MADGIC)5.0g、COOH(CH2)6COOHで表されるスベリン酸(東京化成工業(株))3.1g、及び触媒として第4級ホスホニウム塩であるトリフェニルモノエチルホスホニウムブロミド0.3gをプロピレングリコールモノメチルエーテル8.5gに溶解させた後、120℃に加温し、窒素雰囲気下で4時間撹拌した。得られた反応生成物をプロピレングリコールモノメチルエーテル25.40gにて希釈したワニス溶液のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は約6800であった。この反応生成物は、下記式(10)で表される、硫黄原子を含有しない繰り返し単位構造を有する。
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)、商品名:MADGIC)5.201g、3,3’-チオジプロピオン酸(東京化成工業(株))3.335g、及び触媒として第4級ホスホニウム塩であるトリフェニルモノエチルホスホニウムブロミド0.3764gを、プロピレングリコールモノメチルエーテル13.087gに溶解させた後、120℃で4時間反応させ反応生成物を含む溶液を得た。当該反応生成物を含む溶液のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は約4500であった。この反応生成物は、下記式(11)で表される繰り返し単位構造を有する。
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)、商品名:MADGIC)5.009g、メチレンビス(チオグリコール酸)(東京化成工業(株))3.537g、及び第4級ホスホニウム塩であるトリフェニルモノエチルホスホニウムブロミド0.3625gを、プロピレングリコールモノメチルエーテル13.091gに溶解させた後、120℃で4時間反応させ反応生成物を含む溶液を得た。当該反応生成物を含む溶液のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は約9200であった。この反応生成物は、下記式(12)で表される繰り返し単位構造を有する。
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)、商品名:MADGIC)5.000g、(エチレンジチオ)二酢酸(東京化成工業(株))3.790g、及び第4級ホスホニウム塩であるテトラエチルホスホニウムブロミド(東京化成工業(株))0.3058gを、プロピレングリコールモノメチルエーテル36.384gに溶解させた後、120℃で4時間反応させ反応生成物を含む溶液を得た。当該反応生成物を含む溶液のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は約5200であった。この反応生成物は、下記式(13)で表される繰り返し単位構造を有する。
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)、商品名:MADGIC)5.000g、2,2’-チオジグリコール酸(東京化成工業(株))2.707g、及び第4級ホスホニウム塩であるテトラエチルホスホニウムブロミド(東京化成工業(株))0.3058gを、プロピレングリコールモノメチルエーテル32.049gに溶解させた後、120℃で4時間反応させ反応生成物を含む溶液を得た。当該反応生成物を含む溶液のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は約4500であった。この反応生成物は、下記式(14)で表される繰り返し単位構造を有する。
合成例1で得られた反応生成物0.234gを含む溶液1.459gに、プロピレングリコールモノメチルエーテル19.566g、プロピレングリコールモノメチルエーテルアセテート8.910g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.059g、p-フェノールスルホン酸(東京化成工業(株))0.006g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.001gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例1で得られた反応生成物0.217gを含む溶液1.353gに、プロピレングリコールモノメチルエーテル19.655g、プロピレングリコールモノメチルエーテルアセテート8.910g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.054g、p-フェノールスルホン酸(東京化成工業(株))0.027g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.001gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例1で得られた反応生成物0.223gを含む溶液1.391gにプロピレングリコールモノメチルエーテル19.623g、プロピレングリコールモノメチルエーテルアセテート8.910g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.056g、4-メチルスルフォニルフェノール(Acros Organics社)0.014g、p-フェノールスルホン酸(東京化成工業(株))0.006g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.001gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例1で得られた反応生成物0.233gを含む溶液1.504gに、プロピレングリコールモノメチルエーテル25.460g、プロピレングリコールモノメチルエーテルアセテート2.970g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.058g、4-メチルスルフォニルフェノール(Acros Organics社)0.002g、p-フェノールスルホン酸(東京化成工業(株))0.006g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.005gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例1で得られた反応生成物0.223gを含む溶液1.391gに、プロピレングリコールモノメチルエーテル19.623g、プロピレングリコールモノメチルエーテルアセテート8.910g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.056g、ビスフェノールS(東京化成工業(株))0.014g、p-フェノールスルホン酸(東京化成工業(株))0.006g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.005gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例1で得られた反応生成物0.223gを含む溶液1.391gに、プロピレングリコールモノメチルエーテル19.623g、プロピレングリコールモノメチルエーテルアセテート8.910g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.056g、ビスフェノールAF(東京化成工業(株))0.014g、p-フェノールスルホン酸(東京化成工業(株))0.006g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.005gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例1で得られた反応生成物0.223gを含む溶液1.391gに、プロピレングリコールモノメチルエーテル19.623g、プロピレングリコールモノメチルエーテルアセテート8.910g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.056g、4-シアノフェノール(東京化成工業(株))0.014g、p-フェノールスルホン酸(東京化成工業(株))0.006g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.001gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例1で得られた反応生成物0.223gを含む溶液1.391gに、プロピレングリコールモノメチルエーテル19.623g、プロピレングリコールモノメチルエーテルアセテート8.910g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.056g、3,4,5-トリフルオロフェノール(東京化成工業(株))0.014g、p-フェノールスルホン酸(東京化成工業(株))0.006g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.005gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例2で得られた反応生成物0.234gを含む溶液1.412gに、プロピレングリコールモノメチルエーテル27.038g、プロピレングリコールモノメチルエーテルアセテート1.485g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.059g、5-スルホサリチル酸(東京化成工業(株))0.006g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.001gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例2で得られた反応生成物0.234gを含む溶液1.412gに、プロピレングリコールモノメチルエーテル27.038g、プロピレングリコールモノメチルエーテルアセテート1.485g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.059g、p-フェノールスルホン酸(東京化成工業(株))0.006g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.001gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例5で得られた反応生成物0.927gを含む溶液3.433gにプロピレングリコールモノメチルエーテル23.4g、プロピレングリコールモノメチルエーテルアセテート2.88g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)製、商品名:POWDERLINK〔登録商標〕1174)0.23g、p-フェノールスルホン酸0.023g、界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.018gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例5で得られた反応生成物0.884gを含む溶液3.275gにプロピレングリコールモノメチルエーテル23.5g、プロピレングリコールモノメチルエーテルアセテート2.88g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)製、商品名:POWDERLINK〔登録商標〕1174)0.22g、ビスフェノールS(東京化成工業(株))0.055g、p-フェノールスルホン酸0.022g、界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.018gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例6で得られた反応生成物0.927gを含む溶液3.358gにプロピレングリコールモノメチルエーテル23.5g、プロピレングリコールモノメチルエーテルアセテート2.88g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)製、商品名:POWDERLINK〔登録商標〕1174)0.23g、p-フェノールスルホン酸0.023g、界面活性剤(大日本インキ化学工業(株)製、商品名:R-30)0.018gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例6で得られた反応生成物0.884gを含む溶液3.204gにプロピレングリコールモノメチルエーテル23.6g、プロピレングリコールモノメチルエーテルアセテート2.88g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.22g、ビスフェノールS(東京化成工業(株))0.055g、p-フェノールスルホン酸0.022g、界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.018gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例7で得られた反応生成物0.235gを含む溶液1.293gにプロピレングリコールモノメチルエーテル19.7g、プロピレングリコールモノメチルエーテルアセテート8.91g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.059g、ピリジニウム-p-トルエンスルホネート0.006gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例8で得られた反応生成物0.235gを含む溶液1.265gにプロピレングリコールモノメチルエーテル19.76g、プロピレングリコールモノメチルエーテルアセテート8.91g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)製、商品名:POWDERLINK〔登録商標〕1174)0.059g、ピリジニウム-p-トルエンスルホネート0.006gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例3で得られた反応生成物を含む溶液3.92g(ポリマー濃度20質量%)に、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.20g、ピリジニウム-p-トルエンスルホネート(東京化成工業(株))0.02g、プロピレングリコールモノメチルエーテル6.36g、及び乳酸エチル9.5gを加え、溶液とした。その後、孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
合成例4で得られた反応生成物0.172gを含む溶液0.960gに、プロピレングリコールモノメチルエーテル18.003g、プロピレングリコールモノメチルエーテルアセテート0.989g、テトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)、商品名:POWDERLINK〔登録商標〕1174)0.043g、5-スルホサリチル酸(東京化成工業(株))0.004g、及び界面活性剤(大日本インキ化学工業(株)、商品名:R-30)0.001gを加え、溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過して、レジスト下層膜形成用組成物を調製した。
本明細書に記載の実施例1乃至16及び比較例1,2で調製されたレジスト下層膜形成用組成物を、それぞれスピナーによりシリコンウエハー上に塗布した。ホットプレート上、205℃で1分間ベークし、レジスト下層膜(膜厚0.06μm)を形成した。そして、これらのレジスト下層膜を分光エリプソメーター(J.A.Woollam社製、VUV-VASE VU-302)を用い、波長193nmでのn値(屈折率)及びk値(減衰係数又は吸光係数)を測定した。その結果を表1に示す。
本明細書に記載の実施例1乃至16及び比較例1,2で調製されたレジスト下層膜形成用組成物を、それぞれスピナーによりシリコンウエハー上に塗布した。ホットプレート上、205℃で1分間ベークし、レジスト下層膜を形成した。そして、日本サイエンティフィック(株)製RIEシステムES401を用い、ドライエッチングガスとしてCF4を使用する条件下でドライエッチング速度(単位時間当たりの膜厚の減少量)を測定した。
レジスト下層膜を形成し、その上にレジストパターンを形成する例を次に示す。本明細書に記載の各実施例で調製されたレジスト下層膜形成用組成物を、スピナーにより、シリコンウエハー上にSiON膜(窒素含有酸化珪素膜)のような絶縁膜又はlow-k(低誘電率)膜が例えば0.05μmの厚さに形成された基板上に塗布する。それから、ホットプレート上でベーク(例えば205℃、1分間)し、膜厚20nm乃至30nmのレジスト下層膜を形成する。このレジスト下層膜の上に、市販のフォトレジスト溶液(例えば住友化学(株)製、商品名:PAR855S75)をスピナーにより塗布し、ホットプレート上でベーク(例えば115℃、1分間)して、フォトレジスト膜を形成する。
本明細書に記載の実施例1、2、4乃至8で調製されたレジスト下層膜形成用組成物を、スピナーにより、シリコンウエハー上にSiON膜(窒素含有酸化珪素膜)が0.05μmの厚さに蒸着された基板上に塗布した。それから、ホットプレート上で205℃1分間ベークし、膜厚20nm乃至30nmのレジスト下層膜を形成した。このレジスト下層膜の上に、市販のフォトレジスト溶液(住友化学(株)製、商品名:PAR855S75)をスピナーにより塗布し、ホットプレート上で115℃にて60秒間ベークして、フォトレジスト膜(膜厚0.12μm)を形成した。
Claims (10)
- ジスルフィド結合を主鎖に有するポリマー及び溶剤を含むリソグラフィー用レジスト下層膜形成組成物。
- 前記ポリマーは、2つのエポキシ基を含む少なくとも1種の化合物と、ジスルフィド結合を含む少なくとも1種のジカルボン酸との反応生成物である、請求項1に記載のリソグラフィー用レジスト下層膜形成組成物。
- 前記ポリマーは、下記式(1):
A1乃至A6はそれぞれ独立に、水素原子、メチル基又はエチル基を表し、
Q1はジスルフィド結合を含む2価の基を表し、
nは繰り返し単位構造の数であって、5ないし100の整数を表す。〕
で表される繰り返し単位構造を有する、請求項1又は請求項2に記載のリソグラフィー用レジスト下層膜形成組成物。 - 下記式(1’):
で表される繰り返し単位構造を有するポリマー、及び溶剤を含むリソグラフィー用レジスト下層膜形成組成物。 - 前記ポリマーは、少なくとも1種のジエポキシ化合物と、硫黄原子を有する少なくとも1種のジカルボン酸との反応生成物である、請求項5に記載のリソグラフィー用レジスト下層膜形成組成物。
- 架橋性化合物及びスルホン酸化合物をさらに含む請求項1乃至請求項7のうちいずれか一項に記載のリソグラフィー用レジスト下層膜形成組成物。
- 界面活性剤をさらに含む請求項1乃至請求項8のうちいずれか一項に記載のリソグラフィー用レジスト下層膜形成組成物。
- 請求項1乃至請求項9のうちいずれか一項に記載のリソグラフィー用レジスト下層膜形成組成物を半導体基板上に塗布しベークしてレジスト下層膜を形成する工程、前記レジスト下層膜上にレジストを塗布しベークしてレジスト膜を形成する工程、前記レジスト下層膜と前記レジスト膜で被覆された半導体基板を露光する工程、露光後の前記レジスト膜を現像する工程を含む、半導体装置の製造に用いるレジストパターンの形成方法。
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Also Published As
Publication number | Publication date |
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KR101404141B1 (ko) | 2014-06-10 |
JP5218785B2 (ja) | 2013-06-26 |
US20110053091A1 (en) | 2011-03-03 |
JPWO2009096340A1 (ja) | 2011-05-26 |
EP2237110A4 (en) | 2016-01-20 |
TWI447526B (zh) | 2014-08-01 |
JP2013033276A (ja) | 2013-02-14 |
KR20140040287A (ko) | 2014-04-02 |
TW201001078A (en) | 2010-01-01 |
EP2237110B1 (en) | 2018-07-18 |
JP5382390B2 (ja) | 2014-01-08 |
CN101910948B (zh) | 2012-11-07 |
KR20100126282A (ko) | 2010-12-01 |
EP2237110A1 (en) | 2010-10-06 |
US8318410B2 (en) | 2012-11-27 |
KR101423061B1 (ko) | 2014-07-25 |
CN101910948A (zh) | 2010-12-08 |
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