WO2013005797A1 - 脂環式骨格含有カルバゾール樹脂を含むレジスト下層膜形成組成物 - Google Patents
脂環式骨格含有カルバゾール樹脂を含むレジスト下層膜形成組成物 Download PDFInfo
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- WO2013005797A1 WO2013005797A1 PCT/JP2012/067201 JP2012067201W WO2013005797A1 WO 2013005797 A1 WO2013005797 A1 WO 2013005797A1 JP 2012067201 W JP2012067201 W JP 2012067201W WO 2013005797 A1 WO2013005797 A1 WO 2013005797A1
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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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
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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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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- 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
- C08F26/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/06—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F26/12—N-Vinyl-carbazole
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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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
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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
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/094—Multilayer resist systems, e.g. planarising layers
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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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
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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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/30604—Chemical etching
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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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
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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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3325—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other polycyclic systems
Definitions
- the present invention relates to a resist underlayer film forming composition for lithography effective at the time of processing a semiconductor substrate, a resist pattern forming method using the resist underlayer film forming composition, and a method for manufacturing a semiconductor device.
- BARC Bottom Anti-Reflective Coating
- the resist underlayer film has a selectivity of a dry etching rate close to 1 with respect to the resist dry etching rate.
- Resist underlayer film, resist underlayer film for lithography having a small dry etching rate selectivity to resist dry etching rate, or resist underlayer film for lithography having a low dry etching rate selectivity to semiconductor substrate dry etching rate Is becoming required.
- the polymer for the resist underlayer film include the following.
- a resist underlayer film forming composition using a carbazole novolak resin is exemplified (see Patent Document 1).
- a three-layer process is widely used in which a silicon-containing resist intermediate layer film and a resist lower layer film are formed in the lower layer of the resist.
- the intermediate layer film With the viewpoint of pattern collapse and etching processing accuracy, there is a demand to use the intermediate layer film with a thickness of 50 nm or less.
- the film thickness of the silicon-containing intermediate layer film is 50 nm or less, the antireflection effect of the silicon-containing intermediate layer film is reduced, so that the resist underlayer film is also required to have an appropriate n value and k value.
- a lower layer film having a high n value, a low k value, and transparency and high etching resistance.
- Examples of the polymer for the resist underlayer film having an appropriate n value and k value include the following.
- a resist underlayer film forming composition using a polymer containing a reaction product of naphthol and dicyclopentadiene is exemplified (see Patent Document 2).
- An object of the present invention is to provide a resist underlayer film forming composition for use in a lithography process for manufacturing a semiconductor device. It is another object of the present invention to have an optimum n value and k value in short-wavelength exposure, to prevent intermixing with a resist layer, and to obtain an excellent resist pattern, which is 1 for the resist dry etching rate.
- An object of the present invention is to provide a resist underlayer film for lithography having an etching rate selection ratio. Furthermore, the objective of this invention is providing the formation method of the resist pattern using the resist underlayer film forming composition. An object of the present invention is to provide a resist underlayer film forming composition for forming a resist underlayer film that also has heat resistance.
- a resist underlayer film forming composition comprising a polymer containing a unit structure composed of a reaction product of a condensed heterocyclic compound and a bicyclo ring compound
- the resist underlayer film forming composition according to the first aspect wherein the condensed heterocyclic compound is a carbazole compound or a substituted carbazole compound
- the bicyclo ring compound is dicyclopentadiene, substituted dicyclopentadiene, tetracyclo [4.4.0.1 2,5 . 1 7,10 ] dodeca-3,8-diene or substituted tetracyclo [4.4.0.1 2,5 .
- the resist underlayer film forming composition according to the first aspect or the second aspect
- the polymer includes a unit structure represented by the following formula (1), a unit structure represented by the formula (2), a unit structure represented by the formula (3), or a combination thereof.
- the resist underlayer film forming composition according to claim 1 (In the formula, R 1 to R 14 are hydrogen atom substituents, and each independently represents a halogen group, a nitro group, an amino group, a hydroxy group, or a group having 1 to 10 carbon atoms which may be substituted with these groups.
- Ar is an aromatic ring group having 6 to 40 carbon atoms, and n 1 , n 2 , n 5 , n 6 , n 9 , n 10 , n 13 , n 14, and n 15 are each an integer from 0 to 3, and n 3 , n 4 , n 7 , n 8 , n 11, and n 12 are each an integer from 0 to 4).
- Ar is a phenyl group or a naphthyl group.
- the resist underlayer film forming composition according to the fourth aspect As a sixth aspect, the resist underlayer film forming composition according to any one of the first aspect to the fifth aspect, further including a crosslinking agent, As a seventh aspect, the resist underlayer film forming composition according to any one of the first aspect to the sixth aspect, further comprising an acid and / or an acid generator, As an eighth aspect, a resist underlayer film obtained by applying and baking the resist underlayer film forming composition according to any one of the first to seventh aspects on a semiconductor substrate, As a ninth aspect, the resist underlayer film forming composition according to any one of the first to seventh aspects is applied to a semiconductor substrate and baked to form a lower layer film.
- the resist underlayer film forming composition of the present invention can form a good resist pattern shape without causing intermixing between the upper layer portion of the resist underlayer film and the layer coated thereon.
- the resist underlayer film forming composition of the present invention can be imparted with a performance of effectively suppressing the reflection of exposure light from the substrate, and can also have an effect as an antireflection film for exposure light.
- the resist underlayer film obtained from the resist underlayer film forming composition of the present invention has a high n value and a low k value, and effectively reflects light with a wavelength of 193 nm from the substrate in a three-layer process used in combination with a silicon-containing intermediate layer. Can be reduced.
- a dry etching rate selectivity close to 1 with respect to the resist dry etching rate, a dry etching rate selectivity with respect to the resist dry etching rate, or dry etching of a semiconductor substrate An excellent resist underlayer film having a small dry etching rate selection ratio with respect to the rate can be provided.
- the resist is thinned.
- the resist pattern is transferred to the lower layer film by an etching process, the substrate processing is performed using the lower layer film as a mask, or the resist pattern is transferred to the lower layer film by an etching process, and further to the lower layer film.
- the resist underlayer film and the composition for forming the resist of the present invention are effective for this process.
- a processed substrate for example, a thermal silicon oxide film on the substrate, silicon nitride) Film, polysilicon film, etc. having sufficient etching resistance.
- the resist underlayer film of the present invention can be used as a planarizing film, a resist underlayer film, a resist layer antifouling film, or a film having dry etch selectivity. This makes it possible to easily and accurately form a resist pattern in a lithography process for manufacturing a semiconductor.
- a resist underlayer film by the resist underlayer film forming composition according to the present invention is formed on a substrate, a hard mask is formed thereon, a resist film is formed thereon, a resist pattern is formed by exposure and development, and a resist pattern Is transferred to the hard mask, the resist pattern transferred to the hard mask is transferred to the resist underlayer film, and the semiconductor substrate is processed with the resist underlayer film.
- the hard mask is formed by a coating type composition containing an organic polymer or an inorganic polymer and a solvent, or by vacuum deposition of an inorganic substance.
- an inorganic substance for example, silicon nitride oxide
- a deposit is deposited on the resist underlayer film surface, and the temperature of the resist underlayer film surface rises to around 400 ° C. at that time.
- the polymer used is a polymer containing a carbazole novolak unit structure having high heat resistance
- the resist underlayer film of the present invention has extremely high heat resistance, and does not cause thermal degradation even by deposition of a deposit.
- the present invention is a resist underlayer film forming composition used in a lithography process including a polymer including a unit structure including a reaction product of a condensed heterocyclic compound and a bicyclo ring compound.
- the resist underlayer film forming composition for lithography includes the polymer and a solvent. And this composition can contain a crosslinking agent and an acid, and can contain additives, such as an acid generator and surfactant, as needed.
- the solid content of the composition is 0.1 to 70% by mass, or 0.1 to 60% by mass. The solid content is the content ratio of all components excluding the solvent from the resist underlayer film forming composition.
- the polymer used in the present invention has a weight average molecular weight of 600 to 1000000 or 600 to 200000.
- the condensed heterocyclic compound can be carbazole or substituted carbazole.
- Bicyclo ring compounds include dicyclopentadiene, substituted dicyclopentadiene, and tetracyclo [4.4.0.1 2,5 . 1 7,10 ] dodeca-3,8-diene or substituted tetracyclo [4.4.0.1 2,5 . 1 7,10 ] dodeca-3,8-diene.
- the polymer can be a unit structure represented by the following formula (1), a unit structure represented by the formula (2), a unit structure represented by the formula (3), or a combination thereof.
- R 1 to R 14 are hydrogen atom substituents, each independently having a halogen group, a nitro group, an amino group or a hydroxy group, or those having 1 to 10 carbon atoms which may be substituted with these groups
- Ar is an aromatic ring group having 6 to 40 carbon atoms
- n 1 , n 2 , n 5 , n 6 , n 9 , n 10 , n 13 , N 14 and n 15 are each an integer from 0 to 3
- n 3 , n 4 , n 7 , n 8 , n 11 and n 12 are each an integer from 0 to 4.
- the halogen group includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- alkyl group having 1 to 10 carbon atoms examples include methyl group, ethyl group, n-propyl group, i-propyl group, cyclopropyl group, n-butyl group, i-butyl group, s-butyl group, and t-butyl group.
- Cyclobutyl group 1-methyl-cyclopropyl group, 2-methyl-cyclopropyl group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl Group, 1,1-dimethyl-n-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, cyclopentyl group, 1-methyl -Cyclobutyl, 2-methyl-cyclobutyl, 3-methyl-cyclobutyl, 1,2-dimethyl-cyclopropyl, 2,3-dimethyl-cyclopropyl, 1-ethyl-cyclopropyl Group, 2-ethyl-cyclopropyl group, n-hexyl group, 1-methyl-n-pentyl group, 2-methyl-n-pentyl group, 3-methyl-n-pentyl group, 4-methyl-n-n
- aryl group having 6 to 40 carbon atoms examples include phenyl group, o-methylphenyl group, m-methylphenyl group, p-methylphenyl group, o-chlorophenyl group, m-chlorophenyl group, p-chlorophenyl group, o- Fluorophenyl group, p-fluorophenyl group, o-methoxyphenyl group, p-methoxyphenyl group, p-nitrophenyl group, p-cyanophenyl group, ⁇ -naphthyl group, ⁇ -naphthyl group, o-biphenylyl group, m -Biphenylyl group, p-biphenylyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group and 9-phenanthl
- R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 13 and R 14 are each a hydrogen atom, that is, n 1 , n 2 , n 5 , n 6 , n 9 , n 10 , N 13 and n 14 are each 0.
- R 3 , R 4 , R 7 , R 8 , R 11 and R 12 are each a hydrogen atom, that is, n 3 , n 4 , n 7 , n 8 , n 11 and n 12 are each 0.
- R 3 and R 4 are hydroxy groups
- n 3 and n 4 are each 0 or 1
- R 7 and R 8 are hydroxy groups n 7 and n 8 are each 0 or 1.
- carbazoles used in the present invention include carbazole, 1,3,6,8-tetranitrocarbazole, 3,6-diaminocarbazole, 3,6-dibromo-9-ethylcarbazole, and 3,6-dibromo-9.
- a polymer having a unit structure represented by formulas (1) and (2) can be obtained by addition reaction of dicyclopentadiene and carbazole in the presence of an acid catalyst.
- Acid catalysts used in the reaction include boron trifluoride ethanol complex, Lewis acid such as aluminum chloride, inorganic acid such as hydrochloric acid, nitric acid, sulfuric acid, methanesulfonic acid, n-butanesulfonic acid, benzenesulfonic acid, p-toluenesulfone.
- Super strong acid such as acid, sulfonic acid such as m-xylene sulfonic acid, p-xylene sulfonic acid, and dimethylene sulfonic acid, trifluoromethane sulfonic acid, nonafluoromethane sulfonic acid, and perfluorosulfonic acid such as pentafluorobenzene sulfonic acid And perfluoroalkyl polymers having terminal sulfonic acid groups such as Nafion, anion exchange resins such as polystyrene having sulfonic acid residues, and the like.
- methanesulfonic acid, tosylic acid, and trifluoromethanesulfonic acid can be preferably used.
- a catalyst manufactured by US King Company trade name K-PURE-TAG-2690, trade name K-PURE-TAG-2690, trade name K-PURE-CXC-1614, trade name K-PURE-CXC-1615 is used. You can also The amount used thereof is in the range of 0.01 to 5 mol% with respect to the raw material monomer.
- a methanesulfonic acid-based catalyst 0.01 to 10 mol%, preferably 0.05 to In the case of a trifluoromethanesulfonic acid catalyst, it is in the range of 0.0001 to 5 mol%, preferably 0.0005 to 5 mol%.
- Solvents used in the production of the polymer of the present invention include, for example, ketones such as cyclohexanone and methyl-2-amyl ketone; 3-methoxybutanol, 3-methyl-3-methoxybutanol, 1-methoxy-2-propanol, 1-ethoxy -Alcohols such as 2-propanol; ethers such as propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether, diethylene glycol dimethyl ether; propylene glycol monomethyl ether acetate, propylene glycol Monoethyl ether acetate, ethyl lactate, ethyl pyruvate, butyl acetate, methyl 3-methoxypropionate, -Esters such as ethyl ethoxypropionate, tert-butyl
- the weight average molecular weight Mw of the polymer obtained as described above is usually 600 to 1000000, or 600 to 200000.
- the polymer containing the unit structure of the formula (1), the unit structure of the formula (2), or a combination thereof can be exemplified as follows.
- a condensed heterocyclic compound, a bicyclo ring compound, and hydroxydicyclopentadiene can be copolymerized.
- carbazole, dicyclopentadiene, and hydroxydicyclopentadiene can be copolymerized. In that case, it is considered that hydroxydicyclopentadiene is added to the terminal of the copolymer of carbazole and dicyclopentadiene.
- a condensed heterocyclic compound, a bicyclo ring compound, and an aromatic compound having a hydroxy group and an aldehyde group can be copolymerized.
- carbazole, dicyclopentadiene, and an aromatic compound having a hydroxy group and an aldehyde group can be copolymerized.
- An aromatic compound having a hydroxy group and an aldehyde group binds to the polymer and has an effect of increasing the solubility of the polymer. Thereby, depending on the substituent bonded to carbazole and dicyclopentadiene, the problem that sufficient solubility of the polymer in the solvent cannot be obtained can be solved.
- Carbazole, dicyclopentadiene, and an aromatic compound having a hydroxy group and an aldehyde group are polymerized by a condensation reaction in the presence of an acid.
- aromatic compound having a hydroxy group and an aldehyde group examples include salicylaldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 2,3-dihydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, 2,4-dihydroxybenzaldehyde, 3,5 -Dihydroxybenzaldehyde, 2,3,4-trihydroxybenzaldehyde, 2,4,5-trihydroxybenzaldehyde, 2,4,6-trihydroxybenzaldehyde, 3,4,5-trihydroxybenzaldehyde, 1-hydroxy-2- Naphthylaldehyde, 3-hydroxy-2-naphthylaldehyde, 2-hydroxy-1-naphthylaldehyde, 4-hydroxy-1-naphthylaldehyde, 6-hydroxy-2-naphthylaldehyde De, 2,6-dihydroxy-1-naphthyl aldehyde and
- the said polymer can mix and use another polymer within 30 mass% in all the polymers.
- examples of such other polymers include polyacrylic acid ester compounds, polymethacrylic acid ester compounds, polyacrylamide compounds, polymethacrylamide compounds, polyvinyl compounds, polystyrene compounds, polymaleimide compounds, polymaleic anhydride compounds, and polyacrylonitrile compounds.
- Examples of the raw material monomer for the polyacrylate compound include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2,2,2-trifluoroethyl acrylate, 4-hydroxybutyl acrylate, isobutyl acrylate, tert-butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl acrylate , Tetrahydrofurfuryl acrylate, 3-methoxybutyl acrylate 2-methyl-2-adamantyl acrylate, 2-ethyl-2-adamantyl acrylate, 2-propyl-2
- Examples of the raw material monomer of the polymethacrylate compound include ethyl methacrylate, normal propyl methacrylate, normal pentyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate, phenyl methacrylate, 2-phenylethyl methacrylate, 2 -Hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2,2,2-trifluoroethyl methacrylate, 2,2,2-trichloroethyl methacrylate, methyl acrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, isodecyl methacrylate, normal lauryl methacrylate Normal stearyl methacrylate Methoxydiethylene glycol methacrylate, methoxypolyethylene glycol me
- acrylamide compound examples include acrylamide, N-methylacrylamide, N-ethylacrylamide, N-benzylacrylamide, N-phenylacrylamide, and N, N-dimethylacrylamide.
- Examples of the raw material monomer of the polymethacrylic acid amide compound include methacrylamide, N-methyl methacrylamide, N-ethyl methacrylamide, N-benzyl methacrylamide, N-phenyl methacrylamide, and N, N-dimethyl methacrylamide. .
- Examples of the raw material monomer for the polyvinyl compound include vinyl ether, methyl vinyl ether, benzyl vinyl ether, 2-hydroxyethyl vinyl ether, phenyl vinyl ether, and propyl vinyl ether.
- Examples of the raw material monomer for the polystyrene compound include styrene, methylstyrene, chlorostyrene, bromostyrene, and hydroxystyrene.
- Examples of the raw material monomer of the polymaleimide compound include maleimide, N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.
- polymers are produced by dissolving an addition polymerizable monomer and an optionally added chain transfer agent (10% or less based on the mass of the monomer) in an organic solvent, and then adding a polymerization initiator to perform a polymerization reaction. Then, it can manufacture by adding a polymerization terminator and stopping reaction.
- the addition amount of the polymerization initiator is 1 to 10% with respect to the mass of the monomer
- the addition amount of the polymerization terminator is 0.01 to 0.2% by mass with respect to the mass of the monomer.
- organic solvent used examples include propylene glycol monomethyl ether, propylene glycol monopropyl ether, ethyl lactate, cyclohexanone, methyl ethyl ketone, and dimethylformamide, chain transfer agents such as dodecane thiol and dodecyl thiol, and polymerization initiators such as azo Examples thereof include bisisobutyronitrile and azobiscyclohexanecarbonitrile, and examples of the polymerization terminator include 4-methoxyphenol.
- the reaction temperature is appropriately selected from 30 to 100 ° C.
- the reaction time is appropriately selected from 1 to 48 hours.
- the resist underlayer film forming composition of the present invention can contain a crosslinking agent component.
- the cross-linking agent include melamine type, substituted urea type, or polymer type thereof.
- it is a cross-linking agent having at least two cross-linking substituents, such as methoxymethylated glycoluril such as tetramethoxymethylglycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated Compounds such as benzogwanamine, butoxymethylated benzogwanamine, methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, or methoxymethylated thiourea.
- the condensate of these compounds can also be used.
- crosslinking agent a crosslinking agent having high heat resistance
- a compound containing a crosslinking-forming substituent having an aromatic ring (for example, a benzene ring or a naphthalene ring) in the molecule can be preferably used.
- Examples of this compound include a compound having a partial structure represented by the following formula (4), and a polymer or oligomer having a repeating unit represented by the following formula (5).
- R 16 and R 17 are each a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms
- n 16 is an integer of 1 to 4
- n 17 is an integer of 1 to (5-n 16 )
- (n 16 + n 17 ) is an integer of 2 to 6.
- R 18 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
- R 19 is an alkyl group having 1 to 10 carbon atoms
- n 18 is an integer of 1 to 4
- n 19 is 0 to (4-n 18 )
- (n 18 + n 19 ) is an integer of 1 to 4.
- the oligomer and polymer can be used in the range of 2 to 100 or 2 to 50 repeating unit structures.
- the above compounds can be obtained as products of Asahi Organic Materials Industry Co., Ltd. and Honshu Chemical Industry Co., Ltd.
- the compound of the formula (4-21) can be obtained as Asahi Organic Materials Co., Ltd., trade name TM-BIP-A.
- the amount of the crosslinking agent to be added varies depending on the coating solvent used, the base substrate used, the required solution viscosity, the required film shape, etc., but is 0.001 to 80% by mass with respect to the total solid content, preferably The amount is 0.01 to 50% by mass, more preferably 0.05 to 40% by mass.
- These cross-linking agents may cause a cross-linking reaction by self-condensation, but when a cross-linkable substituent is present in the above-mentioned polymer of the present invention, it can cause a cross-linking reaction with those cross-linkable substituents.
- p-toluenesulfonic acid as a catalyst for promoting the crosslinking reaction, p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthalenecarboxylic acid Acidic compounds such as acids or / and thermal acid generators such as 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and other organic sulfonic acid alkyl esters may be added. I can do it.
- the blending amount is 0.0001 to 20% by mass, preferably 0.0005 to 10% by mass, preferably 0.01 to 3% by mass, based on the total solid content.
- a photoacid generator can be added in order to match the acidity with the photoresist coated on the upper layer in the lithography process.
- Preferred photoacid generators include, for example, onium salt photoacid generators such as bis (4-t-butylphenyl) iodonium trifluoromethanesulfonate, triphenylsulfonium trifluoromethanesulfonate, and phenyl-bis (trichloromethyl) -s.
- -Halogen-containing compound photoacid generators such as triazine, and sulfonic acid photoacid generators such as benzoin tosylate and N-hydroxysuccinimide trifluoromethanesulfonate.
- the photoacid generator is 0.2 to 10% by mass, preferably 0.4 to 5% by mass, based on the total solid content.
- the resist underlayer film forming composition for lithography of the present invention other light absorbers, rheology adjusting agents, adhesion aids, surfactants and the like can be added as necessary in addition to the above.
- the light absorbing agent examples include commercially available light absorbing agents described in “Technical Dye Technology and Market” (published by CMC) and “Dye Handbook” (edited by the Society of Synthetic Organic Chemistry), such as C.I. I. Disperse Yellow 1, 3, 4, 5, 7, 8, 13, 23, 31, 49, 50, 51, 54, 60, 64, 66, 68, 79, 82, 88, 90, 93, 102, 114 and 124; C.I. I. D isprange Orange 1, 5, 13, 25, 29, 30, 31, 44, 57, 72 and 73; I. Disperse Red 1, 5, 7, 13, 17, 19, 43, 50, 54, 58, 65, 72, 73, 88, 117, 137, 143, 199 and 210; I.
- Disperse Violet 43; C.I. I. Disperse Blue 96; C.I. I. Fluorescent Brightening Agent 112, 135 and 163; C.I. I. Solvent Orange 2 and 45; C.I. I. Solvent Red 1, 3, 8, 23, 24, 25, 27 and 49; I. Pigment Green 10; C.I. I. Pigment Brown 2 etc. can be used suitably.
- the above light-absorbing agent is usually blended at a ratio of 10% by mass or less, preferably 5% by mass or less, based on the total solid content of the resist underlayer film forming composition for lithography.
- the rheology modifier mainly improves the fluidity of the resist underlayer film forming composition, and improves the film thickness uniformity of the resist underlayer film and the fillability of the resist underlayer film forming composition inside the hole, particularly in the baking process. It is added for the purpose of enhancing.
- phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, and butyl isodecyl phthalate
- adipic acid derivatives such as dinormal butyl adipate, diisobutyl adipate, diisooctyl adipate, octyl decyl adipate
- maleic acid derivatives such as normal butyl maleate, diethyl maleate and dinonyl maleate
- oleic acid derivatives such as methyl oleate, butyl oleate and tetrahydrofurfuryl oleate
- stearic acid derivatives such as normal butyl stearate and glyceryl stearate. it can.
- These rheology modifiers are usually blended at a ratio of less than 30% by mass with respect to the total solid content of the resist underlayer film
- the adhesion auxiliary agent is added mainly for the purpose of improving the adhesion between the substrate or resist and the resist underlayer film of the present invention, and in particular for preventing the resist from peeling off during development.
- Specific examples include chlorosilanes such as trimethylchlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, chloromethyldimethylchlorosilane, trimethylmethoxysilane, dimethyldiethoxysilane, methyldimethoxysilane, dimethylvinylethoxysilane, diphenyldimethoxysilane, Alkoxysilanes such as enyltriethoxysilane, hexamethyldisilazane, N, N'-bis (trimethylsilyl) urea, silazanes such as dimethyltrimethylsilylamine, trimethylsilylimidazole, vinyltrichlorosilane, ⁇ -chloropropy
- a surfactant can be blended in order to further improve the applicability to surface unevenness without occurrence of pinholes and setups.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene nonyl Polyoxyethylene alkyl allyl ethers such as phenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate Sorbitan fatty acid esters such as rate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sol
- Nonionic surfactants such as polyoxyethylene sorbitan
- the compounding amount of these surfactants is usually 2.0% by mass or less, preferably 1.0% by mass or less, based on the total solid content of the resist underlayer film forming composition for lithography of the present invention.
- These surfactants may be added alone or in combination of two or more.
- the solvent for dissolving the polymer and the crosslinking agent component, the crosslinking catalyst and the like include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-hydroxypropionic acid Ethyl, 2-hydroxy- -Ethyl methyl propionate, ethyl ethioacetate, ethyl hydroxyacetate, 2-hydroxypropionic acid
- a high boiling point solvent such as propylene glycol monobutyl ether or propylene glycol monobutyl ether acetate can be mixed and used.
- a high boiling point solvent such as propylene glycol monobutyl ether or propylene glycol monobutyl ether acetate
- propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, ethyl lactate, butyl lactate, cyclohexanone and the like are preferable for improving the leveling property.
- the resist used in the present invention is a photoresist or an electron beam resist.
- the photoresist applied on the upper part of the resist underlayer film for lithography in the present invention either negative type or positive type can be used, and a positive type photoresist composed of a novolak resin and 1,2-naphthoquinonediazide sulfonic acid ester, depending on the acid.
- Chemically amplified photoresist comprising a binder having a group that decomposes to increase the alkali dissolution rate and a photoacid generator, a low molecular weight compound and photoacid that increases the alkali dissolution rate of the photoresist by decomposition with an alkali-soluble binder and acid
- Chemically amplified photoresist comprising a generator, comprising a binder having a group that decomposes with acid to increase the alkali dissolution rate, a low-molecular compound that decomposes with acid to increase the alkali dissolution rate of the photoresist, and a photoacid generator Chemically amplified photoresist with Si atoms in the skeleton
- a photoresist or the like which, for example, Rohm & Hearts Co., Ltd., and trade name APEX-E.
- an acid is generated by irradiation of a resin containing an Si-Si bond in the main chain and an aromatic ring at the terminal and an electron beam.
- a composition comprising an acid generator, or a composition comprising a poly (p-hydroxystyrene) having a hydroxy group substituted with an organic group containing N-carboxyamine, and an acid generator that generates an acid upon irradiation with an electron beam.
- the acid generated from the acid generator by electron beam irradiation reacts with the N-carboxyaminoxy group of the polymer side chain, and the polymer side chain decomposes into a hydroxy group and exhibits alkali solubility, thus exhibiting alkali development. It dissolves in the liquid to form a resist pattern.
- Acid generators that generate an acid upon irradiation with this electron beam are 1,1-bis [p-chlorophenyl] -2,2,2-trichloroethane, 1,1-bis [p-methoxyphenyl] -2,2,2 -Halogenated organic compounds such as trichloroethane, 1,1-bis [p-chlorophenyl] -2,2-dichloroethane, 2-chloro-6- (trichloromethyl) pyridine, triphenylsulfonium salts, diphenyliodonium salts, etc. Examples thereof include sulfonic acid esters such as onium salts, nitrobenzyl tosylate, and dinitrobenzyl tosylate.
- sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia Inorganic amines such as ethylamine, primary amines such as n-propylamine, secondary amines such as diethylamine and di-n-butylamine, tertiary amines such as triethylamine and methyldiethylamine, dimethylethanolamine, triethanolamine Alcohol amines such as alcohol amines, tetramethylammonium hydroxide, tetraethylammonium hydroxide, quaternary ammonium salts such as choline, and cyclic amines such as pyrrole and piperidine, and alkaline aqueous solutions can be used.
- aqueous ammonia Inorganic amines such as ethylamine, primary amines such as n-propylamine, secondary amines such as diethylamine and di-n-buty
- an appropriate amount of an alcohol such as isopropyl alcohol or a nonionic surfactant may be added to the alkaline aqueous solution.
- preferred developers are quaternary ammonium salts, more preferably tetramethylammonium hydroxide and choline.
- a spinner, a coater, etc. are suitably used on a substrate (for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, an ITO substrate) used for manufacturing a precision integrated circuit device.
- a substrate for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, an ITO substrate
- the resist underlayer film forming composition After applying the resist underlayer film forming composition by various coating methods, it is baked and cured to form a coating type resist underlayer film.
- the thickness of the resist underlayer film is preferably 0.01 to 3.0 ⁇ m.
- the conditions for baking after coating are 80 to 350 ° C. and 0.5 to 120 minutes.
- one or several layers of coating material are formed on the resist underlayer film directly on the resist underlayer film as necessary, and then the resist is applied and irradiated with light or an electron beam through a predetermined mask.
- a good resist pattern can be obtained by performing development, rinsing and drying. If necessary, post-irradiation heating (PEB: Post Exposure Bake) may be performed. Then, the resist underlayer film where the resist has been developed and removed by the above process is removed by dry etching, and a desired pattern can be formed on the substrate.
- PEB Post Exposure Bake
- the exposure light in the photoresist is actinic radiation such as near ultraviolet, far ultraviolet, or extreme ultraviolet (for example, EUV, wavelength 13.5 nm), for example, 248 nm (KrF laser light), 193 nm (ArF laser light), Light having a wavelength such as 157 nm (F 2 laser light) is used.
- the light irradiation can be used without particular limitation as long as it is a method capable of generating an acid from a photoacid generator, and the exposure dose is 1 to 2000 mJ / cm 2 , or 10 to 1500 mJ / cm 2 , or 50. To 1000 mJ / cm 2 .
- the electron beam irradiation of the electron beam resist can be performed using, for example, an electron beam irradiation apparatus.
- a step of forming the resist underlayer film on the semiconductor substrate with the resist underlayer film forming composition a step of forming a resist film thereon, a step of forming a resist pattern by light or electron beam irradiation and development, a resist pattern
- a semiconductor device can be manufactured through a step of etching the resist underlayer film and a step of processing the semiconductor substrate with the patterned resist underlayer film.
- a resist underlayer film for lithography having a selection ratio of a dry etching rate close to 1 with respect to the dry etching rate of the resist
- Lithographic resist underlayer film having a small dry etching rate selectivity to dry etching rate or lithography resist underlayer film having a small dry etching rate selectivity to semiconductor substrate dry etching rate is required. It has become to.
- such a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
- a process of making the resist pattern and the resist underlayer film narrower than the pattern width at the time of developing the resist at the time of the resist underlayer film dry etching has begun to be used.
- a resist underlayer film having a dry etching rate selection ratio close to 1 with respect to the resist dry etching rate is required as a resist underlayer film for such a process. It is becoming. Further, such a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
- the substrate can be processed by selecting an appropriate etching gas. That is, a step of forming a resist underlayer film with a resist underlayer film forming composition on a semiconductor substrate, and a hard mask by a coating material containing a silicon component or the like or a hard mask by vapor deposition (for example, silicon nitride oxide) is formed thereon.
- a semiconductor device can be manufactured through a step of etching the resist underlayer film with an oxygen-based gas or a hydrogen-based gas with a hard mask and a step of processing a semiconductor substrate with a halogen-based gas with a patterned resist underlayer film.
- the resist underlayer film forming composition for lithography of the present invention has a light absorption site incorporated in the polymer skeleton, so that it can be heated or dried. When cured, it does not contain a diffused substance in the photoresist, and the light absorption site has a sufficiently large light absorption performance, so that a resist underlayer film having a high antireflection effect can be formed.
- the resist underlayer film forming composition for lithography of the present invention has high thermal stability, can prevent contamination of the upper layer film by decomposition products during baking, and has a margin in the temperature margin of the baking process. It can be made.
- the resist underlayer film forming composition for lithography of the present invention has a function of preventing reflection of light depending on process conditions, and further prevents the interaction between the substrate and the photoresist or the material used for the photoresist or the photo resist. It can be used as a composition for forming a film having a function of preventing an adverse effect on a substrate of a substance generated upon exposure of a resist.
- This polymer compound was a polymer containing a unit structure of the above formula (3-1).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC of the polymer compound [1] was 2000, and the polydispersity Mw / Mn was 2.90.
- Synthesis Example 2 Synthesis of Polymer Compound [2] Carbazole (15.0 g, 0.090 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) and dicyclopentadiene (11.3 g, 0.085 mol) were placed in a flask under nitrogen. , Tokyo Chemical Industry Co., Ltd.), hydroxydicyclopentadiene (0.81 g, 0.005 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), butyl cellosolve, and trifluoromethanesulfonic acid (0.14 g, 0.0009 mol). , Manufactured by Tokyo Chemical Industry Co., Ltd.), stirred, heated to 140 ° C. and dissolved to start polymerization.
- This polymer compound was a polymer containing a unit structure of the above formula (3-3).
- the weight average molecular weight Mw measured by polystyrene conversion by GPC of the high molecular compound [2] was 3200, and the polydispersity Mw / Mn was 2.80.
- Synthesis Example 3 Synthesis of Polymer Compound [3] Carbazole (4.0 g, 0.024 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), tetracyclo [4.4.0.1 2,5 ] in a flask under nitrogen. . 1 7,10 ] dodeca-3,8-diene (TCDE) (3.8 g, 0.024 mol), butyl cellosolve, trifluoromethanesulfonic acid (0.04 g, 0.0002 mol, Tokyo Chemical Industry Co., Ltd.) And the mixture was stirred and heated to 140 ° C. to dissolve and polymerization was started.
- Carbazole 4.0 g, 0.024 mol, manufactured by Tokyo Chemical Industry Co., Ltd.
- TCDE dodeca-3,8-diene
- TCDE dodeca-3,8-diene
- butyl cellosolve butyl cellosolve
- trifluoromethanesulfonic acid 0.04 g, 0.0002 mol, Tokyo
- This polymer compound was a polymer containing the unit structure of the above formula (3-2).
- the weight average molecular weight Mw measured by polystyrene conversion by GPC of the high molecular compound [3] was 720, and the polydispersity Mw / Mn was 1.24.
- Synthesis Example 4 Synthesis of Polymer Compound [5] Carbazole (10.0 g, 0.060 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), dicyclopentadiene (7.12 g, 0.054 mol) was placed in a flask under nitrogen. , Tokyo Chemical Industry Co., Ltd.), 4-hydroxybenzaldehyde (0.73 g, 0.006 mol, manufactured by Tokyo Chemical Industry Co., Ltd.), butyl cellosolve, trifluoromethanesulfonic acid (0.09 g, 0.0006 mol) , Manufactured by Tokyo Chemical Industry Co., Ltd.) and stirred, heated to 150 ° C. and dissolved to start polymerization.
- This polymer compound was a polymer containing a unit structure represented by the following formula (6-2).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC of the polymer compound [5] was 2070, and the polydispersity Mw / Mn was 2.57.
- Example 1 1.0 g of the polymer compound [1] obtained in Synthesis Example 1 was added to 0.2 g of tetramethoxymethylglycoluril, 0.02 g of pyridinium paratoluenesulfonate, and MegaFac R-30 (manufactured by Dainippon Ink & Chemicals, Inc.). (Trade name) 0.003 g, propylene glycol monomethyl ether 2.3 g, propylene glycol monomethyl ether acetate 4.6 g, and cyclohexanone 16.3 g were mixed to obtain a solution.
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 2 1.0 g of the polymer compound [2] obtained in Synthesis Example 2 was added to 0.2 g of tetramethoxymethylglycoluril, 0.02 g of pyridinium paratoluenesulfonate, and MegaFac R-30 (manufactured by Dainippon Ink & Chemicals, Inc.). (Trade name) 0.003 g, propylene glycol monomethyl ether 2.3 g, propylene glycol monomethyl ether acetate 4.6 g, and cyclohexanone 16.3 g were mixed to obtain a solution.
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 3 1.0 g of the polymer compound [3] obtained in Synthesis Example 3 above, 0.2 g of tetramethoxymethylglycoluril, 0.02 g of pyridinium paratoluenesulfonate, Megafac R-30 (manufactured by Dainippon Ink & Chemicals, Inc.) (Trade name) 0.003 g, propylene glycol monomethyl ether 2.3 g, propylene glycol monomethyl ether acetate 4.6 g, and cyclohexanone 16.3 g were mixed to obtain a solution.
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 4 1.0 g of the polymer compound [5] obtained in Synthesis Example 4 was added to 0.25 g of tetramethoxymethylglycoluril, 0.02 g of pyridinium paratoluenesulfonate, and MegaFac R-30 (manufactured by Dainippon Ink & Chemicals, Inc.).
- Comparative Example 1 1.0 g of the polymer compound [4] obtained in Comparative Synthesis Example 1 above was added to 0.2 g of tetramethoxymethyl glycoluril, 0.02 g of pyridinium paratoluenesulfonate, and MegaFac R-30 (Dainippon Ink Chemical Co., Ltd.) Manufactured, trade name) 0.003 g, propylene glycol monomethyl ether 2.3 g, propylene glycol monomethyl ether acetate 4.6 g, and cyclohexanone 16.3 g were mixed to obtain a solution.
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Each resist underlayer film forming composition solution prepared in Examples 1 to 4 and Comparative Example 1 was applied onto a silicon wafer by a spinner.
- a resist underlayer film (film thickness 0.2 ⁇ m) was formed by heating on a hot plate at a temperature of 250 ° C. for 1 minute. Then, these resist underlayer films were immersed in ethyl lactate, propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate, which are solvents used for the photoresist, and confirmed to be insoluble in the solvent.
- Each resist underlayer film forming composition prepared in Examples 1 to 4 and Comparative Example 1 was applied onto a silicon wafer by a spinner.
- a resist underlayer film (film thickness 0.2 ⁇ m) was formed by heating on a hot plate at a temperature of 250 ° C. for 1 minute.
- These resist underlayer films were subjected to a refractive index (n value) and optical absorption coefficient (k value, attenuation coefficient) at a wavelength of 193 nm using a spectroscopic ellipsometer (manufactured by JA Woollam, VUV-VASE VU-302). (Also called).
- Table 1 Table 1 below.
- the resist underlayer film obtained from the resist underlayer film forming composition according to the present invention has an n value in the range of 1.6 to 1.7 and a k value in the range of 0.1 to 0.3.
- the dry etching rate ratio (selection ratio) in Table 2 is the dry etching rate of each resist underlayer film (resist underlayer film) / (phenol novolac resin film) relative to the dry etching rate of the phenol novolak resin film.
- the resist underlayer film obtained from the resist underlayer film forming composition according to the present invention is different from the conventional high etch rate antireflection film, and is close to 1 with respect to the dry etching rate of the photoresist or the photoresist underlayer film.
- Excellent coating-type resist that has a low dry etching rate selection ratio with respect to the dry etching rate, a low dry etching rate selection ratio with respect to the dry etching rate of the semiconductor substrate, and also has an effect as an antireflection film. It can be seen that an underlayer film can be provided.
- the n value is high and the k value is low.
- it can be used as a resist underlayer film used in a lithography process that can effectively reduce the reflection of light with a wavelength of 193 nm from the substrate. .
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Abstract
Description
上記レジスト下層膜用のポリマーとして例えば以下のものが例示されている。
カルバゾールノボラック樹脂を用いたレジスト下層膜形成組成物が例示されている(特許文献1を参照)。
適切なn値とk値を有する上記レジスト下層膜用のポリマーとして例えば以下のものが例示されている。
ナフトールとジシクロペンタジエンとの反応物を含むポリマーを用いたレジスト下層膜形成組成物が例示されている(特許文献2を参照)。
第2観点として、上記縮合ヘテロ環化合物がカルバゾール化合物、又は置換カルバゾール化合物である第1観点に記載のレジスト下層膜形成組成物、
第3観点として、上記ビシクロ環化合物がジシクロペンタジエン、置換ジシクロペンタジエン、テトラシクロ[4.4.0.12,5.17,10]ドデカ-3,8-ジエン、又は置換テトラシクロ[4.4.0.12,5.17,10]ドデカ-3,8-ジエンである第1観点又は第2観点に記載のレジスト下層膜形成組成物、
第4観点として、上記ポリマーが下記式(1)で表される単位構造、式(2)で表される単位構造、式(3)で表される単位構造又はそれらの組み合わせを含むポリマーである請求項1に記載のレジスト下層膜形成組成物
第5観点として、上記式(3)中、Arがフェニル基又はナフチル基である第4観点に記載のレジスト下層膜形成組成物、
第6観点として、更に架橋剤を含む第1観点乃至第5観点のいずれか一つに記載のレジスト下層膜形成組成物、
第7観点として、更に酸及び/又は酸発生剤を含む第1観点乃至第6観点のいずれか一つに記載のレジスト下層膜形成組成物、
第8観点として、第1観点乃至第7観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって得られるレジスト下層膜、
第9観点として、第1観点乃至第7観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成して下層膜を形成する工程を含む半導体の製造に用いられるレジストパターンの形成方法、
第10観点として、半導体基板上に第1観点乃至第7観点のいずれか一つに記載のレジスト下層膜形成組成物により下層膜を形成する工程、該下層膜上にレジスト膜を形成する工程、光又は電子線の照射と現像により該レジスト膜にレジストパターンを形成する工程、該レジストパターンにより該下層膜をエッチングする工程、及び該パターン化された下層膜により該半導体基板を加工する工程を含む半導体装置の製造方法、
第11観点として、半導体基板に第1観点乃至第7観点のいずれか一つに記載のレジスト下層膜形成組成物により下層膜を形成する工程、該下層膜上にハードマスクを形成する工程、更に該ハードマスク上にレジスト膜を形成する工程、光又は電子線の照射と現像により該レジスト膜にレジストパターンを形成する工程、該レジストパターンにより該ハードマスクをエッチングする工程、該パターン化されたハードマスクにより該下層膜をエッチングする工程、及び該パターン化された下層膜により該半導体基板を加工する工程を含む半導体装置の製造方法、及び
第12観点として、上記ハードマスクが無機物溶液の塗布又は無機物の蒸着により形成される第11観点に記載の製造方法である。
本発明のレジスト下層膜形成組成物から得られるレジスト下層膜は、n値が高くk値が低く、珪素含有中間層と組み合わせて用いる3層プロセスにおいて基板からの波長193nmの光の反射を効果的に低減できる。
本発明において上記のリソグラフィー用レジスト下層膜形成組成物は上記ポリマーと溶剤とを含む。そして、この組成物は架橋剤と酸とを含むことができ、必要に応じて酸発生剤、界面活性剤等の添加剤を含むことができる。この組成物の固形分は0.1乃至70質量%、または0.1乃至60質量%である。固形分はレジスト下層膜形成組成物から溶剤を除いた全成分の含有割合である。固形分中に上記ポリマーを1乃至100質量%、または1乃至99.9質量%、または50乃至99.9質量%、または50乃至95質量%、または50乃至90質量%の割合で含有することができる。
本発明に用いられるポリマーは、重量平均分子量が600乃至1000000、又は600乃至200000である。
特にメタンスルホン酸、トシル酸、トリフルオロメタンスルホン酸を好ましく用いることができる。
また、米国キング社製の触媒、商品名K-PURE-TAG-2689、商品名K-PURE-TAG-2690、商品名K-PURE-CXC-1614、商品名K-PURE-CXC-1615を用いることもできる。
その使用量は、原料モノマーに対して0.01乃至5モル%の範囲であり、例えばメタンスルホン酸系触媒の場合、原料モノマーに対して0.01乃至10モル%、好ましくは0.05乃至5モル%の範囲であり、トリフルオロメタンスルホン酸系触媒の場合で0.0001乃至5モル%、好ましくは0.0005乃至5モル%の範囲である。
それら他のポリマーとしてはポリアクリル酸エステル化合物、ポリメタクリル酸エステル化合物、ポリアクリルアミド化合物、ポリメタクリルアミド化合物、ポリビニル化合物、ポリスチレン化合物、ポリマレイミド化合物、ポリマレイン酸無水物、及びポリアクリロニトリル化合物が挙げられる。
式(4)中、R16及びR17はそれぞれ水素原子、炭素原子数1乃至10のアルキル基、又は炭素原子数6乃至20のアリール基であり、n16は1乃至4の整数であり、n17は1乃至(5-n16)の整数であり、(n16+n17)は2乃至6の整数を示す。
式(5)中、R18は水素原子又は炭素原子数1乃至10のアルキル基であり、R19は炭素原子数1乃至10のアルキル基であり、n18は1乃至4の整数であり、n19は0乃至(4-n18)であり、(n18+n19)は1乃至4の整数を示す。オリゴマー及びポリマーは繰り返し単位構造の数が2乃至100、又は2乃至50の範囲で用いることができる。
これらのアルキル基及びアリール基は、上記アルキル基及びアリール基を例示することができる。
即ち、半導体基板にレジスト下層膜形成組成物によりレジスト下層膜を形成する工程、その上にケイ素成分等を含有する塗膜材料によるハードマスク又は蒸着によるハードマスク(例えば、窒化酸化ケイ素)を形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像により該レジスト膜にレジストパターンを形成する工程、レジストパターンによりハードマスクをハロゲン系ガスでエッチングする工程、パターン化されたハードマスクにより該レジスト下層膜を酸素系ガス又は水素系ガスでエッチングする工程、及びパターン化されたレジスト下層膜によりハロゲン系ガスで半導体基板を加工する工程を経て半導体装置を製造することができる。
本発明のリソグラフィー用レジスト下層膜形成組成物は、熱安定性が高く、焼成時の分解物による上層膜への汚染を防ぐことができるものであり、また、焼成工程の温度マージンに余裕を持たせることができるものである。
さらに、本発明のリソグラフィー用レジスト下層膜形成組成物は、プロセス条件によっては、光の反射を防止する機能と、更には基板とフォトレジストとの相互作用の防止或いはフォトレジストに用いられる材料又はフォトレジストへの露光時に生成する物質の基板への悪作用を防ぐ機能とを有する膜を形成するための組成物としての使用が可能である。
窒素下、フラスコにカルバゾール(13.0g、0.078モル、東京化成工業(株)製)、ジシクロペンタジエン(10.3g、0.078モル、東京化成工業(株)製)、トルエンを仕込み、トリフルオロメタンスルホン酸(0.12g、0.00078モル、東京化成工業(株)製)を加えて撹拌し、120℃まで昇温し溶解させ重合を開始した。21時間後室温まで放冷後、クロロホルム(30g、関東化学(株)製)を加え希釈し、不溶物をろ過で取り除いた後にメタノール(1500g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、20時間乾燥し、目的とする高分子化合物[1]11.6gを得た。この高分子化合物は上記式(3-1)の単位構造を含むポリマーであった。
高分子化合物[1]のGPCによるポリスチレン換算で測定される重量平均分子量Mwは2000、多分散度Mw/Mnは2.90であった。
窒素下、フラスコにカルバゾール(15.0g、0.090モル、東京化成工業(株)製)、ジシクロペンタジエン(11.3g、0.085モル、東京化成工業(株)製)、ヒドロキシジシクロペンタジエン(0.81g、0.005モル、東京化成工業(株)製)、ブチルセロソルブを仕込み、トリフルオロメタンスルホン酸(0.14g、0.0009モル、東京化成工業(株)製)を加えて撹拌し、140℃まで昇温し溶解させ重合を開始した。9時間後室温まで放冷後、クロロホルム(30g、関東化学(株)製)を加え希釈し、不溶物をろ過で取り除いた後にメタノール(1500g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、20時間乾燥し、目的とする高分子化合物[2]18.0gを得た。この高分子化合物は上記式(3-3)の単位構造を含むポリマーであった。
高分子化合物[2]のGPCによるポリスチレン換算で測定される重量平均分子量Mwは3200、多分散度Mw/Mnは2.80であった。
窒素下、フラスコにカルバゾール(4.0g、0.024モル、東京化成工業(株)製)、テトラシクロ[4.4.0.12,5.17,10]ドデカ-3,8-ジエン(TCDE)(3.8g、0.024モル)、ブチルセロソルブを仕込み、トリフルオロメタンスルホン酸(0.04g、0.0002モル、東京化成工業(株)製)を加えて撹拌し、140℃まで昇温し溶解させ重合を開始した。10時間後室温まで放冷後、クロロホルム(30g、関東化学(株)製)を加え希釈し、不溶物をろ過で取り除いた後にメタノール(1500g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、20時間乾燥し、目的とする高分子化合物[3]2.6gを得た。この高分子化合物は上記式(3-2)の単位構造を含むポリマーであった。
高分子化合物[3]のGPCによるポリスチレン換算で測定される重量平均分子量Mwは720、多分散度Mw/Mnは1.24であった。
窒素下、フラスコにカルバゾール(10.0g、0.060モル、東京化成工業(株)製)、ジシクロペンタジエン(7.12g、0.054モル、東京化成工業(株)製)、4-ヒドロキシベンズアルデヒド(0.73g、0.006モル、東京化成工業(株)製)、ブチルセロソルブを仕込み、トリフルオロメタンスルホン酸(0.09g、0.0006モル、東京化成工業(株)製)を加えて撹拌し、150℃まで昇温し溶解させ重合を開始した。21時間後室温まで放冷後、テトラヒドロフラン(6g、関東化学(株)製)を加え希釈し、不溶物をろ過で取り除いた後にメタノール(400g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、20時間乾燥し、目的とする高分子化合物[5]9.1gを得た。この高分子化合物は下記式(6-2)の単位構造を含むポリマーであった。
高分子化合物[5]のGPCによるポリスチレン換算で測定される重量平均分子量Mwは2070、多分散度Mw/Mnは2.57であった。
窒素下、100mL四口フラスコにカルバゾール(10g、0.060mol、東京化成工業(株)製)、ベンズアルデヒド(6.41g、0.060mol、純正化学(株)製)、パラトルエンスルホン酸一水和物(1.19g、0.060mol、関東化学(株)製)を加え、1,4-ジオキサン(15g、関東化学(株)製)を仕込み撹拌し、100℃まで昇温し溶解させ重合を開始した。2時間後60℃まで放冷後、クロロホルム(50g、関東化学(株)製)を加え希釈し、メタノール(250g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で60℃、10時間さらに120℃、24時間乾燥し、目的とする高分子化合物[4]8.64gを得た。これは下記式(6-1)の単位構造を含むポリマーであった。
高分子化合物[4]のGPCによるポリスチレン換算で測定される重量平均分子量Mwは4000、多分散度Mw/Mnは1.69であった。
上記合成例1で得た高分子化合物[1]の1.0gに、テトラメトキシメチルグリコールウリル0.2g、ピリジニウムパラトルエンスルホネート0.02g、メガファックR-30(大日本インキ化学(株)製、商品名)0.003g、プロピレングリコールモノメチルエーテル2.3g、プロピレングリコールモノメチルエーテルアセテート4.6g、シクロヘキサノン16.3gを混合して溶液とした。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濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
上記合成例2で得た高分子化合物[2]の1.0gに、テトラメトキシメチルグリコールウリル0.2g、ピリジニウムパラトルエンスルホネート0.02g、メガファックR-30(大日本インキ化学(株)製、商品名)0.003g、プロピレングリコールモノメチルエーテル2.3g、プロピレングリコールモノメチルエーテルアセテート4.6g、シクロヘキサノン16.3gを混合して溶液とした。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濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
上記合成例3で得た高分子化合物[3]の1.0gに、テトラメトキシメチルグリコールウリル0.2g、ピリジニウムパラトルエンスルホネート0.02g、メガファックR-30(大日本インキ化学(株)製、商品名)0.003g、プロピレングリコールモノメチルエーテル2.3g、プロピレングリコールモノメチルエーテルアセテート4.6g、シクロヘキサノン16.3gを混合して溶液とした。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濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
(実施例4)
上記合成例4で得た高分子化合物[5]の1.0gに、テトラメトキシメチルグリコールウリル0.25g、ピリジニウムパラトルエンスルホネート0.02g、メガファックR-30(大日本インキ化学(株)製、商品名)0.003g、プロピレングリコールモノメチルエーテル2.3g、プロピレングリコールモノメチルエーテルアセテート4.6g、シクロヘキサノン16.3gを混合して溶液とした。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濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
上記比較合成例1で得た高分子化合物[4]の1.0gに、テトラメトキシメチルグリコールウリル0.2g、ピリジニウムパラトルエンスルホネート0.02g、メガファックR-30(大日本インキ化学(株)製、商品名)0.003g、プロピレングリコールモノメチルエーテル2.3g、プロピレングリコールモノメチルエーテルアセテート4.6g、シクロヘキサノン16.3gを混合して溶液とした。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濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
実施例1乃至実施例4及び比較例1で調製した各レジスト下層膜形成組成物溶液を、スピナーにより、シリコンウェハー上に塗布した。ホットプレート上で250℃の温度で1分間加熱し、レジスト下層膜(膜厚0.2μm)を形成した。そして、これらのレジスト下層膜を、フォトレジストに使用する溶剤である、乳酸エチル、プロピレングリコールモノメチルエーテル及びプロピレングリコールモノメチルエーテルアセテートに浸漬し、その溶剤に不溶であることを確認した。
実施例1乃至実施例4及び比較例1で調製した各レジスト下層膜形成組成物を、スピナーにより、シリコンウェハー上に塗布した。ホットプレート上で250℃の温度で1分間加熱し、レジスト下層膜(膜厚0.2μm)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での屈折率(n値)及び光学吸光係数(k値、減衰係数とも称する)を測定した。その結果を下記表1に示す。
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193nm
n値 k値
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実施例1 1.65 0.27
実施例2 1.64 0.26
実施例3 1.66 0.19
実施例4 1.61 0.28
比較例1 1.38 0.38
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ドライエッチング速度の測定には、下記のエッチング装置及びエッチングガスを用いた。
エッチング装置:RIE-10NR(サムコ株式会社製)
エッチングガス:CF4
実施例1乃至実施例4及び比較例1で調製した各レジスト下層膜形成組成物溶液をスピナーにより、シリコンウェハー上に塗布した。ホットプレート上で250℃の温度で1分間加熱し、レジスト下層膜(膜厚0.2μm)を形成した。そのレジスト下層膜に対し、エッチングガスとしてCF4ガスを使用してドライエッチング速度を測定した。さらに、フェノールノボラック樹脂0.7gをプロピレングリコールモノメチルエーテル10gに溶解させた溶液を、スピナーにより、シリコンウェハー上に塗布し、240℃の温度で1分間加熱してフェノールノボラック樹脂膜を形成した。その樹脂膜に対し、エッチングガスとしてCF4ガスを使用してドライエッチング速度を測定し、実施例1乃至実施例3及び比較例1のレジスト下層膜形成組成物から形成された各レジスト下層膜のドライエッチング速度との比較を行った。その結果を下記表2に示す。表2のドライエッチング速度比(選択比)は、上記フェノールノボラック樹脂膜のドライエッチング速度に対する各レジスト下層膜のドライエッチング速度(レジスト下層膜)/(フェノールノボラック樹脂膜)である。
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ドライエッチング速度比
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実施例1 0.82
実施例2 0.84
実施例3 0.88
実施例4 0.85
比較例1 0.78
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Claims (12)
- 縮合ヘテロ環化合物とビシクロ環化合物との反応物からなる単位構造を含むポリマーを含むレジスト下層膜形成組成物。
- 上記縮合ヘテロ環化合物がカルバゾール化合物、又は置換カルバゾール化合物である請求項1に記載のレジスト下層膜形成組成物。
- 上記ビシクロ環化合物がジシクロペンタジエン、置換ジシクロペンタジエン、テトラシクロ[4.4.0.12,5.17,10]ドデカ-3,8-ジエン、又は置換テトラシクロ[4.4.0.12,5.17,10]ドデカ-3,8-ジエンである請求項1又は請求項2に記載のレジスト下層膜形成組成物。
- 上記ポリマーが下記式(1)で表される単位構造、式(2)で表される単位構造、式(3)で表される単位構造又はそれらの組み合わせを含むポリマーである請求項1に記載のレジスト下層膜形成組成物。
- 上記式(3)中、Arがフェニル基又はナフチル基である請求項4に記載のレジスト下層膜形成組成物。
- 更に架橋剤を含む請求項1乃至請求項5のいずれか1項に記載のレジスト下層膜形成組成物。
- 更に酸及び/又は酸発生剤を含む請求項1乃至請求項6のいずれか1項に記載のレジスト下層膜形成組成物。
- 請求項1乃至請求項7のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって得られるレジスト下層膜。
- 請求項1乃至請求項7のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成して下層膜を形成する工程を含む半導体の製造に用いられるレジストパターンの形成方法。
- 半導体基板上に請求項1乃至請求項7のいずれか1項に記載のレジスト下層膜形成組成物により下層膜を形成する工程、該下層膜上にレジスト膜を形成する工程、光又は電子線の照射と現像により該レジスト膜にレジストパターンを形成する工程、該レジストパターンにより該下層膜をエッチングする工程、及び該パターン化された下層膜により該半導体基板を加工する工程を含む半導体装置の製造方法。
- 半導体基板に請求項1乃至請求項7のいずれか1項に記載のレジスト下層膜形成組成物により下層膜を形成する工程、該下層膜上にハードマスクを形成する工程、更に該ハードマスク上にレジスト膜を形成する工程、光又は電子線の照射と現像により該レジスト膜にレジストパターンを形成する工程、該レジストパターンにより該ハードマスクをエッチングする工程、該パターン化されたハードマスクにより該下層膜をエッチングする工程、及び該パターン化された下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
- 上記ハードマスクが無機物溶液の塗布又は無機物の蒸着により形成される、請求項11に記載の製造方法。
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KR1020147002852A KR101913101B1 (ko) | 2011-07-07 | 2012-07-05 | 지환식 골격 함유 카바졸 수지를 포함하는 레지스트 하층막 형성 조성물 |
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EP3623867A1 (en) | 2018-09-13 | 2020-03-18 | Shin-Etsu Chemical Co., Ltd. | Patterning process |
US11635691B2 (en) | 2019-07-05 | 2023-04-25 | Shin-Etsu Chemical Co., Ltd. | Composition for forming organic film, substrate for manufacturing semiconductor device, method for forming organic film, patterning process, and polymer |
EP3761115A1 (en) | 2019-07-05 | 2021-01-06 | Shin-Etsu Chemical Co., Ltd. | Composition for forming organic film, substrate for manufacturing semiconductor device, method for forming organic film, patterning process, and polymer |
Also Published As
Publication number | Publication date |
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JP6041104B2 (ja) | 2016-12-07 |
JPWO2013005797A1 (ja) | 2015-02-23 |
KR20140051931A (ko) | 2014-05-02 |
TWI553035B (zh) | 2016-10-11 |
KR101913101B1 (ko) | 2018-10-31 |
TW201305238A (zh) | 2013-02-01 |
CN103635858A (zh) | 2014-03-12 |
CN103635858B (zh) | 2017-09-29 |
US20140235060A1 (en) | 2014-08-21 |
US9343324B2 (en) | 2016-05-17 |
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