WO2014017331A1 - Composition de formation de film de couche supérieure de réserve pour lithographie et procédé permettant de fabriquer un dispositif à semi-conducteurs qui utilise cette dernière - Google Patents

Composition de formation de film de couche supérieure de réserve pour lithographie et procédé permettant de fabriquer un dispositif à semi-conducteurs qui utilise cette dernière Download PDF

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Publication number
WO2014017331A1
WO2014017331A1 PCT/JP2013/069278 JP2013069278W WO2014017331A1 WO 2014017331 A1 WO2014017331 A1 WO 2014017331A1 JP 2013069278 W JP2013069278 W JP 2013069278W WO 2014017331 A1 WO2014017331 A1 WO 2014017331A1
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upper layer
resist
layer film
resist upper
forming composition
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PCT/JP2013/069278
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English (en)
Japanese (ja)
Inventor
竜慈 大西
徳昌 藤谷
木村　茂雄
坂本　力丸
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日産化学工業株式会社
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Publication of WO2014017331A1 publication Critical patent/WO2014017331A1/fr

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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
    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/3236—Heterocylic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—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

Definitions

  • the present invention is used in a manufacturing process of a semiconductor device using photolithography, reduces an adverse effect exerted by exposure light, and is effective for obtaining a good resist pattern.
  • the present invention relates to a resist pattern forming method using a resist upper layer film forming composition and a method for manufacturing a semiconductor device using the forming method.
  • a thin film of a photoresist composition is formed on a substrate to be processed such as a silicon wafer, and then actinic rays such as ultraviolet rays are irradiated and developed through a mask pattern on which a semiconductor device pattern is drawn.
  • the substrate to be processed such as a silicon wafer is etched using the obtained photoresist pattern as a protective film (mask).
  • the degree of integration of semiconductor devices has increased, and the active light used has also been shortened from a KrF excimer laser (wavelength 248 nm) to an ArF excimer laser (wavelength 193 nm).
  • an antireflection film (Bottom Anti-Reflective Coating, The method of providing BARC) has been widely adopted.
  • an inorganic antireflection film such as titanium, titanium dioxide, titanium nitride, chromium oxide, carbon, and ⁇ -silicon, and an organic antireflection film made of a light-absorbing substance and a polymer compound are known.
  • the former requires equipment such as a vacuum deposition apparatus, a CVD apparatus, and a sputtering apparatus for film formation, whereas the latter is advantageous in that no special equipment is required, and many studies have been made.
  • the upper layer of the EUV resist is beryllium, boron, carbon, silicon, zirconium, niobium.
  • a method comprising a polymer comprising a group comprising one or more of molybdenum (Patent Document 1, Patent Document 2).
  • Non-patent Document 1 a top coat formed of a polyhydroxystyrene (PHS) compound or an acrylic compound is applied to the upper layer of the EUV resist to reduce OOB (Non-patent Document 1),
  • PHS polyhydroxystyrene
  • Non-Patent Document 2 a EUV resolution enhancement layer film is applied to the upper layer of the EUV resist and the EUV resist resolution is improved by absorbing OOB (Non-Patent Document 2), but what composition is optimal is disclosed. Absent.
  • the present invention has been made to provide an optimal resist upper layer film forming composition that solves the above-mentioned problems, and is used as a resist upper layer film, particularly as an upper layer film of an EUV resist, without intermixing with the resist.
  • a composition for forming a resist upper layer film used in a lithography process for manufacturing a semiconductor device which is capable of selectively transmitting only EUV by blocking exposure light, such as UV or DUV, which is not preferable in EUV exposure, and capable of developing with a developer after exposure. Offer things.
  • (Formula 1-1) (Substituents A 1 to A 3 in (Formula 1-1) are each a substituent containing at least one hydroxyl group, and at least one substituent is a naphthalene ring or an anthracene ring.
  • a benzene ring, the hydrogen atoms of the naphthalene ring, anthracene ring or benzene ring are each independently substituted with a halogen atom or a linear or branched saturated alkyl group having 1 to 4 carbon atoms.
  • a resist upper layer film-forming composition comprising a cyanurate derivative represented by formula (II) and an alcohol solvent
  • the resist upper layer film-forming composition according to the first aspect wherein the cyanurate derivative is synthesized from 1,3,5-tris- (2,3-epoxypropyl) isocyanurate
  • the cyanurate derivative is a cyanurate derivative synthesized from 1,3,5-tris- (2,3-epoxypropyl) isocyanurate and a hydroxyl group-containing compound D.
  • the hydroxyl group-containing compound D is a compound represented by i) or a combination of compounds represented by ii).
  • the cyanurate derivative may be 1,3,5-tris- (2,3-epoxypropyl) isocyanurate and a compound represented by the following (formula 1-2), or (formula 1-2):
  • n1 and n4 are each independently an integer of 1 to 5
  • n2 and n3 are each independently an integer of 0 to 8
  • n6 is each independently an integer of 0 to 4
  • (n1 + n2 + n3) is an integer of 1 to 9
  • (n4 + n5 + n6) is an integer of 1 to 5
  • (n1 + n4) is an integer of 2 to
  • the alcohol solvent is a straight chain having 1 to 20 carbon atoms, a branched or cyclic saturated alkyl alcohol having 3 to 20 carbon atoms, or an aromatic alcohol having 6 to 20 carbon atoms.
  • the resist upper layer film-forming composition according to any one of the viewpoints to the fourth aspect,
  • the alcohol solvent is 1-heptanol, 2-methyl-1-butanol, 2-methyl-2-butanol, 4-methyl-2-pentanol, or cyclopentanol.
  • the resist upper layer film-forming composition according to any one of the five aspects As a seventh aspect, the resist upper layer film-forming composition according to any one of the first aspect to the sixth aspect, further including an acid compound, As an eighth aspect, the resist upper layer film-forming composition according to the seventh aspect, in which the acid compound is a sulfonic acid compound or a sulfonic acid ester compound, As a ninth aspect, the resist upper layer film-forming composition according to the seventh aspect, wherein the acid compound is an onium salt-based acid generator, a halogen-containing compound-based acid generator, or a sulfonic acid-based acid generator, As a tenth aspect, the resist upper layer film-forming composition according to any one of the first to ninth aspects, further including a basic compound, As an eleventh aspect, the resist upper layer film forming composition according to any one of the first aspect to the tenth aspect, wherein the resist used together with the composition is a resist for EUV (wavelength 13.5 nm), As a twelfth
  • the present invention provides a resist upper layer film-forming composition, in particular, an EUV resist upper layer film-forming composition, which does not intermix with the EUV resist, and blocks EUV exposure, such as UV or DUV, which is not preferable for EUV exposure.
  • the present invention relates to a resist upper layer film-forming composition that is selectively transmitted and can be developed with a developer after exposure.
  • the EUV light when the EUV resist is exposed, the EUV light emits UV light and DUV light together with the EUV light. That is, this EUV light contains about 5% of light having a wavelength of 300 nm or less in addition to EUV light.
  • the wavelength region in the vicinity of 190 nm to 300 nm, particularly 220 nm to 260 nm has the highest intensity.
  • the solvent used for the EUV resist is not used, and the resist upper layer film forming composition is an alcohol solvent. It is better to use in the resist upper layer film forming composition of the present invention, a cyanurate derivative containing a hydroxyl group is used in order to enhance the solubility in an alcohol solvent. Since the cyanurate derivative used in the resist upper layer film-forming composition of the present invention contains a hydroxyl group, it can be dissolved in a developer (for example, an alkaline developer) together with an EUV resist during development after exposure. Dissolution removal with a liquid is possible.
  • a developer for example, an alkaline developer
  • the present invention is a resist upper layer film-forming composition containing a cyanurate derivative and an alcohol solvent. Although suitable as a resist upper layer film, it is particularly suitable as a resist upper layer film forming composition used in an EUV lithography process using EUV as an exposure wavelength.
  • the cyanurate compound for forming the cyanurate derivative used in the resist upper layer film-forming composition of the present invention has the following structure.
  • each of R 1 , R 2 , and R 3 is independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a benzene derivative group, vinyl Derivative group or epoxy derivative group is represented.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-octyl, and n-dodecyl. Is done.
  • the benzene derivative group include a phenyl group, a benzyl group, a tolyl group, a methoxyphenyl group, a xylyl group, a biphenyl group, a naphthyl group, and an anthryl group.
  • Examples of the vinyl derivative group include an ethenyl group, a propenyl group, a butenyl group, a butadienyl group, a hexenyl group, and an octadienyl group.
  • Examples of the epoxy derivative group include a glycidyl group and a ⁇ -methyl-glycidyl group. These alkyl groups, benzene derivative groups, and vinyl derivative groups may be substituted in addition to unsubstituted groups.
  • Examples of the substituents include halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, Examples are a hydroxyl group, an alkoxy group and an acyl group. A particularly preferred substituent is a hydroxyl group.
  • 1,3,5-tris- (2,3-epoxypropyl) isocyanurate represented by (Formula 3-2) is more preferably used.
  • the above isocyanurate compound is reacted with an aromatic ring compound having a specific structure described below to synthesize a cyanurate derivative used in the resist upper layer film-forming composition of the present invention.
  • the cyanurate derivative used in the present invention has the following structure (formula 1-1).
  • the compound of the formula (1-1) is synthesized by reacting a cyanurate compound with an aromatic ring compound having a specific structure.
  • the aromatic ring compound having a specific structure is a compound containing a naphthalene ring or anthracene ring containing at least one hydroxyl group in the structure.
  • Substituents A 1 to substituents A 3 are each a substituent containing at least one hydroxyl group, further at least one substituent is a naphthalene ring or an anthracene ring, the other When a substituent is present, it is a benzene ring.
  • a compound containing a naphthalene ring or an anthracene ring and a compound containing a benzene ring When a compound containing a naphthalene ring or an anthracene ring and a compound containing a benzene ring are reacted at the same time, a compound containing a naphthalene ring or an anthracene ring and a benzene ring coexists in the substituent A 1 to the substituent A 3.
  • the hydrogen atoms of the naphthalene ring, anthracene ring or benzene ring may be each independently substituted with a halogen atom or a linear or branched saturated alkyl group having 1 to 4 carbon atoms.
  • the hydroxyl group is a hydrophilic group and is excellent in solubility in an alcohol solvent and in a developer.
  • the reason for introducing a naphthalene ring or an anthracene ring into the cyanurate derivative is to absorb the UV light or DUV light.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Examples of the linear or branched saturated alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. It is done.
  • the hydroxyl group-containing compound D to be reacted with the cyanurate compound is a compound represented by the following i) or a combination of compounds represented by ii).
  • i) 1 selected from naphthoic acid or anthracenecarboxylic acid which contains at least one hydroxyl group as a substituent and may contain a halogen atom or a linear or branched saturated alkyl group having 1 to 4 carbon atoms as a substituent.
  • the compound represented by i) or the combination of compounds represented by ii) includes a compound containing two or more carboxyl groups, a compound in which two or more cyanurate compounds are linked by the compound is formed.
  • the compound constituting i) may be one kind or a combination of two or more kinds, but is preferably within 4 kinds, more preferably within 3 kinds.
  • the compound constituting ii) may be a combination of one or more compounds selected from the naphthoic acid or anthracene carboxylic acid and one or more combinations of the benzoic acid, more preferably the naphthoic acid or anthracene carboxylic acid. A combination of 3 or less compounds selected from acids and 3 or less of the above benzoic acids.
  • the compound to be reacted with the cyanurate compound is a compound represented by the general formula (formula 1-2), or a compound represented by the formula (1-2)
  • a compound containing one carboxyl group represented by a combination of compounds represented by 1-3) is preferably used.
  • the compound having the structure of (Formula 1-2) may be one kind or a combination of two or more kinds, but is preferably within 4 kinds, more preferably within 3 kinds.
  • the compound having the structure of (Formula 1-3) may be one kind or a combination of two or more kinds, but preferably within 4 kinds, more preferably within 3 kinds.
  • a compound in which two or more cyanurate compounds are linked with each other may be formed, which is not preferable as the composition component of the present invention.
  • the carboxyl group in the compound represented by (Formula 1-2) or (Formula 1-3) reacts with a cyanurate derivative, particularly preferably reacts with an epoxy group to form a trimethyl group such as (Formula 1-1). An ester compound is produced.
  • n1 and n4 are each independently an integer of 1 to 5, preferably an integer of 1 to 3, and n2 and n3 are each independently 0 Is an integer from 1 to 8, more preferably an integer from 0 to 3, n5 and n6 are each independently an integer from 0 to 4, more preferably an integer from 0 to 3, and (n1 + n2 + n3) is 1. Is an integer from 1 to 9, (n4 + n5 + n6) is an integer from 1 to 5, and (n1 + n4) is an integer from 2 to 9.
  • m1 represents 1 or 2.
  • X represents a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom).
  • the resist upper layer film-forming composition of the present invention contains the above cyanurate derivative and an alcohol solvent, and may further contain an acid compound, a basic compound, a crosslinking agent, a crosslinking catalyst, a surfactant, a rheology modifier and the like.
  • the molecular weight of the cyanurate compound used in the present invention is 129 to 1000, preferably 129 to 600.
  • combined from a cyanurate compound is fluctuate
  • the resist upper layer film using the cyanurate derivative may diffuse into the photoresist to deteriorate the lithography performance.
  • the weight average molecular weight is 10,000 or more, the solubility of the resist upper layer film to be formed in the photoresist developer is insufficient, and a residue may be present after development.
  • the total compound to be reacted with the cyanurate compound is 100% by mass, 30% by mass to 100% by mass, more preferably 50% by mass to 100% by mass, more preferably 70% by mass to 100% by mass, More preferably, it is 76 mass% to 100 mass%.
  • the content of the cyanurate derivative in the resist upper layer film forming composition in the solid content is 20% by mass or more, for example, 20 to 100% by mass, or 30 to 100% by mass, or 50 to 90% by mass, or 60 to 80% by mass. %.
  • the solid content of the resist upper layer film-forming composition of the present invention is 0.1 to 50% by mass, preferably 0.3 to 30% by mass.
  • the solid content is obtained by removing the solvent component from the resist upper layer film-forming composition.
  • the reaction between the cyanurate compound and the aromatic ring-containing compound is preferably performed in a nitrogen atmosphere.
  • the reaction temperature may be selected from 50 ° C. to 200 ° C., preferably 80 ° C. to 180 ° C.
  • a high molecular weight cyanurate derivative can be obtained in a reaction time of 1 to 48 hours.
  • a reaction time of 1 to 24 hours at 80 to 150 ° C. is more preferable.
  • solvents that can be used in this case include alcohol solvents such as 1-butanol, 2-butanol, isobutyl alcohol, tert-butyl alcohol, 1-pentanol, 2-pentanol, 3-pentanol, 1-heptanol, 2 -Heptanol, tert-amyl alcohol, neopentyl alcohol, 2-methyl-1-propanol, 2-methyl-1-butanol, 2-methyl-2-butanol, 3-methyl-1-butanol, 3-methyl-3- Pentanol, cyclopentanol, 1-hexanol, 2-hexanol, 3-hexanol, 2,3-dimethyl-2-butanol, 3,3-dimethyl-1-butanol, 3,3-dimethyl-2-butanol, 2 -Diethyl-1-butanol, 2-methyl-1
  • solvents 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 Propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-hydroxyethyl propionate, 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, hydroxyethyl acetate, 2-hydroxy-3-methylbutanoate, 3-methoxy Methyl propionate 3 over methoxypropionate, ethyl 3 over ethyl ethoxypropionate, 3 over ethoxypropionate, methyl pyru
  • the solution containing the cyanurate derivative thus obtained can be used as it is for the preparation of the resist upper layer film-forming composition.
  • the cyanurate derivative may be precipitated and isolated in a poor solvent such as methanol, ethanol, ethyl acetate, hexane, toluene, acetonitrile, water, and recovered for use.
  • the drying conditions after isolating the cyanurate derivative are preferably 6 to 48 hours at 40 to 100 ° C. in an oven or the like.
  • the cyanurate derivative After the cyanurate derivative is recovered, it can be redissolved in an arbitrary solvent, preferably the alcohol solvent described below, and used as a resist upper layer film composition.
  • the resist upper layer film-forming composition of the present invention is applied to the above cyanurate derivative in place of a solvent usually used for resists and the film is formed on the resist.
  • the following alcohol solvents are preferably used.
  • the saturated alkyl alcohol may be a straight chain having 1 to 20 carbon atoms, a branched or cyclic saturated alkyl alcohol having 3 to 20 carbon atoms, such as 1-butanol, 2-butanol, isobutyl alcohol, tert-butyl alcohol, 1- Pentanol, 2-pentanol, 3-pentanol, 1-heptanol, 2-heptanol, tert-amyl alcohol, neopentyl alcohol, 2-methyl-1-propanol, 2-methyl-1-butanol, 2-methyl- 2-butanol, 3-methyl-1-butanol, 3-methyl-3-pentanol, cyclopentanol, 1-hexanol, 2-hexanol, 3-hexanol, 2,3-dimethyl-2-butanol, 3,3 -Dimethyl-1-butanol, 3,3-dimethyl-2-butane 2-diethyl-1-butanol,
  • aromatic alcohol examples include aromatic alcohols having 6 to 20 carbon atoms such as 1-phenylpropanol, 2-phenylpropanol, 3-phenylpropanol, 2-phenoxyethanol, phenethyl alcohol, and styryl alcohol.
  • Preferred alcohol solvents are 1-heptanol, 2-methyl-1-butanol, 2-methyl-2-butanol, 4-methyl-2-pentanol or cyclopentanol. These alcohol solvents can be used alone or as a mixture.
  • the following solvents may be mixed together with the alcohol solvent.
  • the solvent is 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 propyl ether Acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxypropionic acid Methyl
  • the resist upper layer film forming composition of the present invention may further contain an acid compound in order to match the acidity with the resist present in the lower layer in the lithography process.
  • an acid compound a sulfonic acid compound or a sulfonic acid ester compound can be used.
  • the blending amount is 0.02 to 10% by mass, preferably 0.04 to 5% by mass, per 100% by mass of the total solid content.
  • an acid is irradiated by exposure light (for example, ArF excimer laser irradiation, EUV irradiation, electron beam irradiation, etc.).
  • a generated acid generator can be added.
  • Preferred acid generators include, for example, onium salt acid generators such as bis (4-tert-butylphenyl) iodonium trifluoromethanesulfonate, triphenylsulfonium trifluoromethanesulfonate, and phenyl-bis (trichloromethyl) -s-triazine.
  • halogen-containing compound acid generators such as benzoin tosylate and sulfonic acid acid generators such as N-hydroxysuccinimide trifluoromethanesulfonate.
  • the amount of the acid generator added is 0.02 to 10% by mass, preferably 0.04 to 5% by mass, per 100% by mass of the total solid content.
  • the resist upper layer film-forming composition of the present invention can contain a basic compound.
  • a basic compound such as amine reacts with an acid generated from a photoacid generator during exposure to reduce the sensitivity of the resist underlayer film, thereby controlling the upper shape of the resist after exposure and development (after exposure and development).
  • the resist shape is preferably rectangular.
  • the basic compound include amines.
  • r 1 to r 5 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an amino group.
  • alkyl group examples include methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, -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 group, 2 -Methyl-cyclobutyl group, 3-methyl-cyclobutyl group, 1,2-dimethyl-cyclopropyl group, 2,3-dimethyl-cyclo
  • Examples of the compound include the following formulas (13-2) to (13-47).
  • tertiary amines such as zabicyclooctane and aromatic amines such as pyridine and 4-dimethylaminopyridine.
  • primary amines such as benzylamine and normal butylamine, and secondary amines such as diethylamine and dinormalbutylamine are also included. These compounds can be used alone or in combination of two or more.
  • composition for forming a resist upper layer film of the present invention may contain additional rheology modifiers, surfactants and the like as necessary.
  • the rheology modifier is added mainly for the purpose of improving the fluidity of the resist upper layer film-forming composition.
  • phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, and butyl isodecyl phthalate; Mention may be made of 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, or 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 100% by mass of the total composition of the resist upper layer film-forming composition.
  • a surfactant can be blended in order to further improve the applicability to surface unevenness.
  • 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 aryl 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 Nonionic surfactants such as polyoxyethylene sorbititan sorbit
  • the compounding amount of these surfactants is usually 0.2% by mass or less, preferably 0.1% by mass or less, per 100% by mass of the total composition of the resist upper layer film-forming composition of the present invention.
  • These surfactants may be added alone or in combination of two or more.
  • an EUV resist can be used.
  • the EUV resist applied to the lower layer of the resist upper layer film formed from the composition of the present invention either a negative type or a positive type can be used.
  • Chemically amplified resist comprising a binder having a group that decomposes with an acid generator and an acid to change the alkali dissolution rate, a low molecular weight compound that decomposes with an alkali-soluble binder, an acid generator and an acid to change the alkali dissolution rate of the resist
  • a chemically amplified resist comprising: a binder having a group that decomposes with an acid generator and an acid to change the alkali dissolution rate; and a chemically amplified resist comprising a low-molecular compound that decomposes with an acid to change the alkali dissolution rate of the resist,
  • non-chemically amplified resists composed of binders having groups that decompose by EUV to change the alkali dissolution rate, and non-chemical
  • EUV resist As the material system of EUV resist, there are methacrylic system, polyhydroxystyrene (PHS) system, and the like. When these EUV resists are used, a resist pattern can be formed in the same manner as when a resist is used with the irradiation source as an electron beam.
  • PHS polyhydroxystyrene
  • a KrF resist or an ArF resist can be used.
  • a negative photoresist or a positive photoresist can be used.
  • a positive photoresist comprising a novolac resin and 1,2-naphthoquinonediazide sulfonic acid ester, a chemically amplified photoresist comprising a binder having a group that decomposes with an acid to increase the alkali dissolution rate and a photoacid generator, an acid
  • a chemically amplified photoresist comprising a low-molecular compound that decomposes to increase the alkali dissolution rate of the photoresist, an alkali-soluble binder, and a photoacid generator, and a binder having a group that decomposes with an acid to increase the alkali dissolution rate
  • a chemically amplified photoresist composed of a low molecular weight compound that decomposes with an acid to increase the alkali dissolution rate of the photoresist and a photoacid generator.
  • an electron beam resist can be used.
  • a negative photoresist or a positive photoresist can be used.
  • Chemically amplified resist comprising a binder having a group that decomposes with an acid generator and an acid to change the alkali dissolution rate, a low molecular weight compound that decomposes with an alkali-soluble binder, an acid generator and an acid to change the alkali dissolution rate of the resist
  • a chemically amplified resist comprising: a binder having a group that decomposes with an acid generator and an acid to change the alkali dissolution rate; and a chemically amplified resist comprising a low-molecular compound that decomposes with an acid to change the alkali dissolution rate of the resist,
  • non-chemically amplified resists composed of a binder having a group that changes the alkali dissolution rate by being decom
  • 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.
  • amines such as ethylamine, primary amines such as n-propylamine, secondary amines such as diethylamine and di-n-butylamine, tertiary amine
  • 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 step of forming an EUV resist film on a substrate having a film to be processed for forming a transfer pattern, with or without using an EUV resist lower layer film, the EUV resist upper layer of the present invention on the resist film A step of applying and baking a film-forming composition to form an EUV resist upper layer film, a step of exposing a semiconductor substrate coated with the resist upper layer film and the resist film, and developing after exposure to remove the resist upper layer film and the resist film A semiconductor device can be manufactured. Exposure is performed by EUV (wavelength 13.5 nm).
  • the resist upper layer film is generally formed by a spin coating method in the same manner as the resist film formation.
  • a resist coat is formed on a substrate to be processed (for example, a silicon / silicon dioxide coated substrate, a glass substrate, an ITO substrate, etc.) on a spin coater manufactured by Tokyo Electron, and the resist upper layer film of the present invention is formed.
  • the forming composition (varnish) is applied to the substrate to be processed at a spin speed of 700 rpm to 3000 rpm and then baked on a hot plate at 50 ° C. to 150 ° C. for 30 to 300 seconds to form the resist upper layer film.
  • the film thickness of the resist upper layer film is 3 to 100 nm, 5 to 100 nm, or 5 to 50 nm.
  • the dissolution rate of the resist upper layer film formed from the composition of the present invention in the photoresist developer is 1 nm or more per second, preferably 3 nm or more per second, and more preferably 10 nm or more per second.
  • the dissolution rate is smaller than this, the time required for removing the resist upper layer film becomes longer, resulting in a decrease in productivity.
  • development is performed using a resist developer, thereby removing the resist and unnecessary portions of the resist upper layer film to form a resist pattern.
  • the semiconductor device to which the composition for forming an EUV resist upper layer film of the present invention is applied has a structure in which a film to be processed to transfer a pattern, a resist film, and a resist upper layer film formed from the composition are sequentially formed on a substrate.
  • This resist upper layer film can form a resist pattern having a good straight shape by reducing adverse effects exerted by the base substrate and EUV, and can provide a sufficient margin for the EUV irradiation amount.
  • the resist upper layer film according to the present invention has a wet etching rate equal to or greater than that of the resist film formed in the lower layer, and can be easily removed with an alkali developer together with unnecessary portions of the resist film after exposure. Is possible.
  • the substrate to be processed of the semiconductor device can be processed by either dry etching or wet etching.
  • a resist pattern that is well formed can be used as a mask, and dry etching or wet etching can be used. It is possible to transfer a good shape to the substrate to be processed.
  • a step of forming a KrF resist film with or without a KrF resist underlayer film on a substrate having a processing target film for forming a transfer pattern, and the KrF resist according to the present invention on the resist film A step of applying and baking an upper layer film-forming composition to form a KrF resist upper layer film, a step of exposing a semiconductor substrate covered with the resist upper layer film and the resist film, and developing after exposure to develop the resist upper layer film and the resist film A semiconductor device can be manufactured. Exposure is performed with KrF.
  • the resist upper layer film is formed in the same manner as in the EUV exposure.
  • an ArF resist film is formed on a substrate having a film to be processed on which a transfer pattern is to be formed, with or without an ArF resist underlayer film, and the ArF resist according to the present invention is formed on the resist film.
  • a step of applying and baking an upper layer film forming composition to form an ArF resist upper layer film, a step of exposing a semiconductor substrate coated with the resist upper layer film and the resist film, and developing after exposure to develop the resist upper layer film and the resist film A semiconductor device can be manufactured. Exposure is performed with ArF.
  • the resist upper layer film is formed in the same manner as in the EUV exposure.
  • an electron beam resist film is formed on a substrate having a processing target film for forming a transfer pattern, with or without an electron beam resist underlayer film, and the present invention is applied to the resist film.
  • a step of applying and baking an electron beam resist upper layer film forming composition to form an electron beam resist upper layer film a step of exposing the resist upper layer film and a semiconductor substrate coated with the resist film, and developing after exposure to the resist upper layer film
  • a step of removing the resist film a semiconductor device can be manufactured. Exposure is performed with an electron beam.
  • the resist upper layer film is formed in the same manner as in the EUV exposure.
  • 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).
  • GPC gel permeation chromatography
  • the measurement conditions etc. are as follows using the GPC apparatus by Tosoh Corporation for the measurement.
  • the dispersity shown in the following synthesis examples of the present specification is calculated from the measured weight average molecular weight and number average molecular weight.
  • the cyanurate derivative solution does not cause white turbidity even when cooled to room temperature, and has good solubility in cyclohexanol.
  • the obtained cyanurate derivative had a weight average molecular weight of 1673 in terms of standard polystyrene and a dispersity of 1.69.
  • the cyanurate derivative solution does not cause white turbidity even when cooled to room temperature, and has good solubility in cyclohexanol.
  • the obtained cyanurate derivative had a weight average molecular weight of 1453 and a dispersity of 1.41 in terms of standard polystyrene.
  • the cyanurate derivative solution does not cause white turbidity even when cooled to room temperature, and has good solubility in cyclohexanol.
  • the obtained cyanurate derivative had a weight average molecular weight of 1373 in terms of standard polystyrene and a dispersity of 1.25.
  • the cyanurate derivative solution does not cause white turbidity even when cooled to room temperature, and has good solubility in cyclohexanol.
  • the obtained cyanurate derivative had a weight average molecular weight of 1073 and a dispersity of 1.41 in terms of standard polystyrene.
  • the cyanurate derivative solution does not cause white turbidity even when cooled to room temperature, and has good solubility in cyclohexanol.
  • the obtained cyanurate derivative had a weight average molecular weight of 1546 in terms of standard polystyrene and a dispersity of 1.90.
  • the cyanurate derivative solution does not cause white turbidity even when cooled to room temperature, and has good solubility in cyclohexanol.
  • the obtained cyanurate derivative had a weight average molecular weight of 1559 in terms of standard polystyrene and a dispersity of 1.75.
  • the cyanurate derivative solution does not cause white turbidity even when cooled to room temperature, and has good solubility in cyclohexanol.
  • the obtained cyanurate derivative had a weight average molecular weight of 1166 in terms of standard polystyrene and a dispersity of 1.40.
  • the cyanurate derivative solution does not cause white turbidity even when cooled to room temperature, and has good solubility in cyclohexanol.
  • the obtained cyanurate derivative had a weight average molecular weight of 1225 and a dispersity of 1.11.
  • cyanurate derivative had a weight average molecular weight of 756 and a dispersity of 1.05 in terms of standard polystyrene.
  • the cyanurate derivative solution does not cause white turbidity even when cooled to room temperature, and has good solubility in cyclohexanol.
  • the obtained cyanurate derivative had a weight average molecular weight of 1265 and a dispersity of 1.12.
  • Example 1 20.4 g of 4-methyl-2-pentanol was dissolved in 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 1 above. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist upper layer film forming composition for lithography.
  • Example 2 20.4 g of 4-methyl-2-pentanol was dissolved in 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 2 above. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist upper layer film forming composition for lithography.
  • Example 3 20.4 g of 4-methyl-2-pentanol was dissolved in 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 3 above. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist upper layer film forming composition for lithography.
  • Example 4 20.4 g of 4-methyl-2-pentanol was dissolved in 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 4 above. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist upper layer film forming composition for lithography.
  • Example 5 20.4 g of 4-methyl-2-pentanol was dissolved in 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 5 above. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist upper layer film forming composition for lithography.
  • Example 6 20.4 g of 4-methyl-2-pentanol was dissolved in 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 6 above. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist upper layer film forming composition for lithography.
  • Example 7 To 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 7, 20.4 g of 4-methyl-2-pentanol was added and dissolved. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist upper layer film forming composition for lithography. (Example 8) 20.4 g of 4-methyl-2-pentanol was dissolved in 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 8 above.
  • Example 9 20.4 g of 1-heptanol was added to 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 1 and dissolved. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist upper layer film forming composition for lithography.
  • Example 10 20.4 g of cyclopentanol was dissolved in 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 1 above.
  • Example 11 20.4 g of 2-methyl-1-butanol was added to 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 1 and dissolved. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist upper layer film forming composition for lithography.
  • Example 12 To 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 1 above and 0.0032 g of bis (4-hydroxyphenyl) sulfone, 20.4 g of 4-methyl-2-pentanol was added and dissolved. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist upper layer film forming composition for lithography. (Example 13) To 1.0 g of a solution containing 0.32 g of the cyanurate derivative obtained in Synthesis Example 1 and 0.0032 g of 2,6-diisopropylaniline, 20.4 g of 4-methyl-2-pentanol was added and dissolved.
  • the maximum value of the absorptance was 40% or more as good and less than 40% as bad.
  • the transmittance of EUV light (13.5 nm)
  • a transmittance of 80% or more was considered good and less than 80% was regarded as defective.
  • the resist upper layer film obtained from the resist upper layer film forming composition of each example is superior to the resist upper layer film obtained from the resist upper layer film forming composition of Comparative Example 1 and Comparative Example 2 in DUV light shielding properties. It became the result.
  • Comparative Example 3 the light shielding property of the DUV light was good, but it did not dissolve in the developer in the resist intermixing test described above, and thus the desired required characteristics were not satisfied.
  • the present invention provides an EUV lithography process that selectively transmits only EUV by blocking unwanted exposure light, such as UV and DUV, for example, without intermixing with a resist, and developing with a developer after exposure. It can be used as a composition for forming an EUV resist upper layer film to be used or a resist upper layer film for a lithography process at other exposure wavelengths.

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Abstract

Le problème à résoudre dans le cadre de la présente invention consiste à proposer une composition de formation de film de couche supérieure de réserve qui doit être utilisée pour un procédé de lithographie lors d'une procédure de fabrication d'un dispositif à semi-conducteurs qui est exempt de phénomènes d'entremêlement avec une réserve et transmet de manière sélective seulement un rayonnement ultraviolet extrême tout en bloquant la lumière d'exposition qui n'est pas souhaitable telle que le rayonnement ultraviolet et le rayonnement ultraviolet dangereux spécialement pendant une exposition au rayonnement ultraviolet extrême. Cette composition de formation de film de couche supérieure de réserve peut être développée avec un liquide développeur après l'exposition. La solution proposée consiste en une composition de formation de film de couche supérieure de réserve qui contient : un dérivé obtenu par réaction d'un dérivé de cyanurate avec un composé qui contient un noyau naphtalène ou un noyau anthracène ; et un solvant à base d'alcool.
PCT/JP2013/069278 2012-07-25 2013-07-16 Composition de formation de film de couche supérieure de réserve pour lithographie et procédé permettant de fabriquer un dispositif à semi-conducteurs qui utilise cette dernière WO2014017331A1 (fr)

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