WO2012067040A1 - レジスト下層膜形成組成物及びそれを用いたレジストパターンの形成方法 - Google Patents
レジスト下層膜形成組成物及びそれを用いたレジストパターンの形成方法 Download PDFInfo
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- WO2012067040A1 WO2012067040A1 PCT/JP2011/076083 JP2011076083W WO2012067040A1 WO 2012067040 A1 WO2012067040 A1 WO 2012067040A1 JP 2011076083 W JP2011076083 W JP 2011076083W WO 2012067040 A1 WO2012067040 A1 WO 2012067040A1
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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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- 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
-
- 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 a composition useful for forming a resist underlayer film between a substrate and a resist film formed thereon in order to obtain a resist pattern having a desired shape in a lithography process in the process of manufacturing a semiconductor device.
- the present invention also relates to a composition for forming a resist underlayer film suitable for a lithography process using EUV exposure.
- Patent Document 1 As a material for forming a resist underlayer film for EUV exposure, a resist underlayer film forming composition with reduced outgas generation is disclosed (Patent Document 1). In addition, although not a material specified for EUV exposure, a resist underlayer film forming composition containing a reaction product of a bifunctional diglycidyl ester compound and 2,4-dihydroxybenzoic acid is also disclosed (Patent Document) 2). However, these Patent Documents 1 and 2 do not describe or suggest a two-dimensional polymer obtained by a polyaddition reaction between a bifunctional diglycidyl ester compound and bisphenol S or a derivative thereof.
- the cross section in the direction perpendicular to the substrate of the resist pattern formed on the resist underlayer film is preferably rectangular.
- the aromatic ring density in the resist underlayer film is increased.
- the resist underlayer film is required to have a higher dry etching rate than that of the resist film (a large selection ratio of the dry etching rate).
- a resist underlayer film formed from a composition containing a polymer that is an acrylic resin or a methacrylic resin is not always satisfactory with respect to the dry etching rate. This is probably because the bonds between carbon atoms (CC bond) constituting the main chain of the acrylic resin or methacrylic resin are not easily broken by dry etching.
- the pattern line width to be formed is 32 nm or less, and the demand for line edge roughness (hereinafter abbreviated as LER in this specification) of the pattern side wall becomes severe.
- LER line edge roughness
- the formed resist pattern shape is a skirt shape or a shape in which adjacent patterns are connected without being separated, the LER value when observed from above the pattern becomes large, which adversely affects dimensional control. For this reason, it is strongly required to make the resist pattern shape a rectangular shape having a small LER value.
- the present invention includes an aromatic ring such as a benzene ring, the selectivity of the dry etching rate with respect to the resist film is large, and the LER which is a big problem in EUV (wavelength 13.5 nm) lithography is used. It aims at obtaining the composition for forming the resist underlayer film useful for reduction.
- Another object of the present invention is to obtain a composition for forming a resist underlayer film in which a resist pattern on the resist underlayer film has a desired shape.
- the resist underlayer film to be formed is insoluble in the solvent of the resist applied thereon, and no intermixing occurs between the resist underlayer film to be formed and the resist film. It is a condition.
- a resist underlayer film for lithography comprising a polymer and a solvent, wherein the polymer has diphenylsulfone or a derivative thereof introduced into the main chain of the polymer through an ether bond.
- the ether bond is represented by “—O—”.
- the oxygen atom of the ether bond is usually bonded to a carbon atom to form a C—O bond.
- the polymer has, as a main chain, the following formula (1a) and the following formula (1b): (Wherein R 1 , R 2 , R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, a hydroxyl group, a methoxy group, a thiol group, an acetyl group, a nitro group, an allyl group) Group, phenyl group, naphthyl group, A 1 , A 2 , A 3 , A 4 , A 5 and A 6 each independently represents a hydrogen atom, a methyl group or an ethyl group, and Q represents two carbon atoms. Represents a divalent organic group in between.)
- a resist underlayer film forming composition for lithography having a repeating structural unit represented by
- Q is the following formula (2): (Wherein Q 1 represents an alkylene group having 1 to 10 carbon atoms, a divalent organic group having an alicyclic hydrocarbon ring having 3 to 10 carbon atoms, a phenylene group, a naphthylene group or an anthrylene group, Group, naphthylene group and anthrylene group are each an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a cyano group, and an alkylthio group having 1 to 6 carbon atoms. It may be substituted with at least one group selected from the group consisting of It is represented by
- Q is also represented by the following formula (3):
- X 1 is the following formula (4) or the following formula (5):
- R 5 and R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a benzyl group or a phenyl group, Substituted with at least one group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a cyano group, and an alkylthio group having 1 to 6 carbon atoms R 5 and R 6 may be bonded to each other to form a ring having 3 to 6 carbon atoms.
- X 1 represents formula (5)
- the carbonyl group of formula (5) is bonded to the nitrogen atom of formula (3).
- the repeating structural unit represented by the formula (1b) further includes a structural unit in which Q is represented by the formula (2) in addition to the structural unit represented by the formula (3). May be.
- Q is also the following formula (6): (Wherein R 7 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a benzyl group or a phenyl group, and the phenyl group is an alkyl group having 1 to 6 carbon atoms, (It may be substituted with at least one group selected from the group consisting of a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a cyano group, and an alkylthio group having 1 to 6 carbon atoms.) But it is also represented.
- the repeating structural unit represented by the formula (1b) further includes a structural unit in which Q is represented by the formula (2) in addition to the structural unit represented by the formula (6). May be.
- the polymer has the following formula (7): It may further have a repeating structural unit represented by
- the alkyl group is, for example, a methyl group, an ethyl group, an isopropyl group, an n-butyl group, or a cyclohexyl group.
- the alkylene group having 1 to 10 carbon atoms include methylene group, ethylene group, n-propylene group, n-pentylene group, n-octylene group, 2-methylpropylene group, 1,4-dimethylbutylene group, and cyclopentylene.
- the alicyclic hydrocarbon ring having 3 to 10 carbon atoms is, for example, a cyclohexane ring or an adamantane ring.
- the alkoxy group having 1 to 6 carbon atoms is, for example, a methoxy group, an ethoxy group, an n-pentyloxy group, an isopropoxy group, or a cyclohexyloxy group.
- Examples of the alkylthio group having 1 to 6 carbon atoms are a methylthio group, an ethylthio group, an n-pentylthio group, an isopropylthio group, and a cyclohexylthio group.
- the alkenyl group having 3 to 6 carbon atoms is, for example, a 2-propenyl group or a 3-butenyl group.
- the alkyl group, alkylene group, alkoxy group and alkylthio group are not limited to a straight chain, and may have a branched structure or a cyclic structure.
- the halogen atom is, for example, fluorine, chlorine, bromine or iodine.
- the number of repeating structural units represented by the formula (1a) and the formula (1b) is, for example, in the range of 10 or more and 10,000 or less.
- Solvents contained in the resist underlayer film forming composition of the present invention include, for example, propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monopropyl ether, methyl ethyl ketone, ethyl lactate, cyclohexanone, ⁇ -butyrolactone, N-methylpyrrolidone, a mixture of two or more selected from these solvents.
- the ratio of the said solvent with respect to the resist underlayer film forming composition of this invention is 50 to 99.5 mass%, for example.
- the polymer contained in the resist underlayer film forming composition of the present invention can be in a proportion of, for example, 0.5% by mass to 30% by mass with respect to the resist underlayer film forming composition.
- the resist underlayer film forming composition of the present invention may contain a crosslinkable compound (crosslinking agent) in addition to the polymer and the solvent, and may further contain a compound that promotes a crosslinking reaction.
- a crosslinkable compound crosslinking agent
- the component excluding the solvent is defined as a solid content
- the solid content includes additives such as the polymer, the crosslinkable compound added as necessary, and the compound that promotes the crosslink reaction.
- the ratio of the polymer in the solid content is, for example, 70% by mass or more and 98% by mass or less. When an additive is not included, the ratio of the polymer in the solid content can be 100% by mass.
- the crosslinkable compound is, for example, a nitrogen-containing compound having 2 to 4 nitrogen atoms substituted with a methylol group or an alkoxymethyl group.
- the crosslinkable compound is 1 for the polymer contained in the resist underlayer film forming composition of the present invention. It can be added in a proportion of not less than 30% by mass.
- Specific examples of the cross-linkable compound include hexamethoxymethyl melamine, tetramethoxymethyl benzoguanamine, 1,3,4,6-tetrakis (methoxymethyl) glycoluril, 1,3,4,6-tetrakis (butoxymethyl) glycoluril.
- 1,3,4,6-tetrakis (hydroxymethyl) glycoluril, 1,3-bis (hydroxymethyl) urea, 1,1,3,3-tetrakis (butoxymethyl) urea and 1,1,3,3 -Tetrakis (methoxymethyl) urea.
- the compound that promotes the crosslinking reaction is at least one selected from, for example, a sulfonic acid compound and a thermal acid generator.
- stimulates the said crosslinking reaction can be added with respect to the polymer contained in the resist underlayer film forming composition of this invention in the ratio of 0.1 to 10 mass%, for example.
- the sulfonic acid compound examples include p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium-p-toluenesulfonate, camphorsulfonic acid, 5-sulfosalicylic acid, 4-chlorobenzenesulfonic acid, 4-hydroxybenzenesulfonic acid, benzene Examples include disulfonic acid and 1-naphthalenesulfonic acid.
- thermal acid generator examples include 4-acetoxyphenyldimethylsulfonium hexafluoroarsenate, benzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, 4-acetoxyphenylbenzylmethylsulfonium hexafluoroantimonate, dibenzyl-4- Hydroxyphenylsulfonium hexafluoroantimonate, 4-acetoxyphenylbenzylsulfonium hexafluoroantimonate, 3-benzylbenzothiazolium hexafluoroantimonate, 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2 -Nitrobenzyl tosylate.
- the resist underlayer film forming composition of the present invention may contain a surfactant and / or an adhesion assistant.
- the surfactant is an additive for improving applicability to the substrate.
- a known surfactant such as a nonionic surfactant or a fluorine-based surfactant can be used, and it can be added at a ratio of, for example, 0.2% by mass or less to the resist underlayer film forming composition of the present invention. it can.
- the adhesion auxiliary agent is an additive for the purpose of improving the adhesion between the substrate or the resist film and the resist underlayer film, and is an additive that suppresses peeling of the resist film during development after exposure.
- chlorosilanes, alkoxysilanes, silazanes, silanes, and heterocyclic compounds can be used, and they are added at a ratio of, for example, 2% by mass or less with respect to the resist underlayer film forming composition of the present invention. Can do.
- the second aspect of the present invention includes a step of applying the resist underlayer film forming composition of the present invention on a semiconductor substrate and baking to form a resist underlayer film, a step of forming a resist film on the resist underlayer film,
- a resist pattern forming method used for manufacturing a semiconductor device comprising: exposing a resist underlayer film and a semiconductor substrate covered with the resist film; and developing the resist film after exposure.
- the exposure performed in the second aspect of the present invention can be performed using EUV (wavelength 13.5 nm) or an electron beam.
- EUV is an abbreviation for extreme ultraviolet light.
- the resist for forming the resist film may be either a positive type or a negative type.
- a chemically amplified resist that is sensitive to EUV or electron beam can be used.
- the semiconductor substrate used in the second aspect of the present invention is typically a silicon wafer, but is an SOI (Silicon on Insulator) substrate, or gallium arsenide (GaAs), indium phosphide (InP), gallium phosphide (A compound semiconductor wafer such as GaP) may be used.
- SOI Silicon on Insulator
- GaAs gallium arsenide
- InP indium phosphide
- GaP gallium phosphide
- a compound semiconductor wafer such as GaP may be used.
- the resist underlayer film forming composition of the present invention contains a polymer in which diphenyl sulfone or a derivative thereof is introduced into the main chain through an ether bond.
- a polymer in which diphenyl sulfone or a derivative thereof is introduced into the main chain through an ether bond for example, a two-dimensional polymer having a repeating structural unit represented by the formula (1a) and the formula (1b) is included. Therefore, a resist underlayer film having a large selection ratio of the dry etching rate to the resist film can be obtained without reducing the aromatic ring density.
- the contained polymer is, for example, an acrylic resin or A resist underlayer film having a higher dry etching rate can be formed than using a conventional resist underlayer film forming composition that is a methacrylic resin.
- the density of the resist underlayer film to be formed can be increased, and the desired shape (on the substrate)
- a resist pattern having a rectangular cross section in the vertical direction can be formed.
- the polymer contained in the resist underlayer film forming composition of the present invention has the following formula (8a): (Wherein R 1 , R 2 , R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, a hydroxyl group, a methoxy group, a thiol group, an acetyl group, a nitro group, an allyl group) Represents a group, a phenyl group or a naphthyl group.) And at least one compound represented by the following formula (8b): Wherein A 1 , A 2 , A 3 , A 4 , A 5 and A 6 each independently represents a hydrogen atom, a methyl group or an ethyl group, and Q is a divalent organic group between two carbon atoms. Represents a group.) A polyaddition reaction product with at least one compound represented by the formula:
- a catalyst that activates an epoxy group by dissolving at least one compound represented by formula (8a) and at least one compound represented by formula (8b) in an organic solvent so as to have an appropriate molar ratio.
- a polymer having a repeating structural unit represented by the formula (1a) and the formula (1b) can be obtained.
- Bisphenol S is an example of a compound represented by the formula (8a).
- the catalyst for activating the epoxy group include a quaternary phosphonium salt such as ethyltriphenylphosphonium bromide and a quaternary ammonium salt such as benzyltriethylammonium chloride, which are represented by the formula (8a) used.
- An appropriate amount can be selected from the range of 0.1 to 10% by mass with respect to the total mass of the compound represented by formula (8b) and the compound represented by formula (8b).
- the optimum temperature and time for the polymerization reaction can be selected from the range of 80 to 160 ° C. and 2 to 50 hours.
- Q is, for example, the following formula (9): (Wherein Q 1 represents an alkylene group having 1 to 10 carbon atoms, a divalent organic group having an alicyclic hydrocarbon ring having 3 to 10 carbon atoms, a phenylene group, a naphthylene group or an anthrylene group, Group, naphthylene group and anthrylene group are each an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a cyano group, and an alkylthio group having 1 to 6 carbon atoms. It may be substituted with at least one group selected from the group consisting of It is represented by
- the compound represented by the formula (8b) is, for example, the following formula (10): Wherein Y represents an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a cyano group, or an alkylthio group having 1 to 6 carbon atoms, and m is 0 Represents an integer of 1 to 4, and when m is 2 to 4, Y may be the same or different. It is represented by When m represents 0, it means that there is no substituent represented by Y.
- Q is also represented by the following formula (11): (Wherein R 7 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a benzyl group or a phenyl group, and the phenyl group is an alkyl group having 1 to 6 carbon atoms, (It may be substituted with at least one group selected from the group consisting of a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a cyano group, and an alkylthio group having 1 to 6 carbon atoms.) But it is also represented.
- the repeating structural unit of the polymer contained in the resist underlayer film forming composition of the present invention is exemplified by the following formulas (21) to (25).
- the polymer having a repeating structural unit represented by the formula (21) includes a compound represented by the formula (8a) and a compound represented by the formula (8b) (represented by the formula (10)).
- the polymer having a repeating structural unit represented by the formula (22) includes a compound represented by the formula (8a) and a compound represented by the formula (8b) (a compound represented by the formula (10)). It is obtained by polymerizing 2,4-dihydroxybenzoic acid.
- the molar ratio of the structural unit represented by a and the structural unit represented by b is 1: 1.
- the molar ratio of the structural unit represented by a and the structural unit represented by b is 1: 1.
- the molar ratio of the structural unit represented by a and the structural unit represented by b is 1: 1.
- the molar ratio of the structural unit represented by a and the structural unit represented by b is 1: 1.
- the weight average molecular weights shown in the following Synthesis Examples 1 to 3 are based on measurement results by gel permeation chromatography (hereinafter abbreviated as GPC in this specification).
- GPC gel permeation chromatography
- a GPC device manufactured by Tosoh Corporation was used, and the measurement conditions were as follows.
- Example 1 To 10 g of the solution containing 2 g of the polymer obtained in Synthesis Example 1, 0.5 g of tetramethoxymethylglycoluril (manufactured by Nippon Cytec Industries, Ltd., trade name: Powderlink [registered trademark] 1174) and pyridinium-p-toluenesulfonate 0.05 g was mixed and dissolved in 35.4 g of propylene glycol monomethyl ether and 18.6 g of ethyl lactate to obtain a solution. Then, it filtered using the polyethylene micro filter with the hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition.
- tetramethoxymethylglycoluril manufactured by Nippon Cytec Industries, Ltd., trade name: Powderlink [registered trademark] 1174
- pyridinium-p-toluenesulfonate 0.05 g was
- Example 2 To 10 g of the solution containing 2 g of the polymer obtained in Synthesis Example 2, 0.5 g of tetramethoxymethylglycoluril (manufactured by Nippon Cytec Industries, Ltd., trade name: Powderlink [registered trademark] 1174) and pyridinium-p-toluenesulfonate 0.05 g was mixed and dissolved in 35.4 g of propylene glycol monomethyl ether and 18.6 g of ethyl lactate to obtain a solution. Then, it filtered using the polyethylene micro filter with the hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition.
- tetramethoxymethylglycoluril manufactured by Nippon Cytec Industries, Ltd., trade name: Powderlink [registered trademark] 1174
- pyridinium-p-toluenesulfonate 0.05 g was
- Example 3 To 10 g of the solution containing 2 g of the polymer obtained in Synthesis Example 3, 0.5 g of tetramethoxymethylglycoluril (manufactured by Nippon Cytec Industries, Ltd., trade name: Powderlink [registered trademark] 1174) and pyridinium-p-toluenesulfonate 0.05 g was mixed and dissolved in 35.4 g of propylene glycol monomethyl ether and 18.6 g of ethyl lactate to obtain a solution. Then, it filtered using the polyethylene micro filter with the hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition.
- tetramethoxymethylglycoluril manufactured by Nippon Cytec Industries, Ltd., trade name: Powderlink [registered trademark] 1174
- pyridinium-p-toluenesulfonate 0.05 g was
- Example 4 To 10 g of a solution containing 2 g of the polymer obtained in Synthesis Example 4 above, 0.5 g of tetramethoxymethyl glycoluril (manufactured by Nippon Cytec Industries, Inc., trade name: Powderlink [registered trademark] 1174) and pyridinium-p-toluenesulfonate 0.03 g was mixed and dissolved in 34.5 g of propylene glycol monomethyl ether and 18.2 g of ethyl lactate to obtain a solution. Then, it filtered using the polyethylene micro filter with the hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition.
- tetramethoxymethyl glycoluril manufactured by Nippon Cytec Industries, Inc., trade name: Powderlink [registered trademark] 1174
- pyridinium-p-toluenesulfonate 0.03 g
- Example 5 To 10 g of the solution containing 2 g of the polymer obtained in Synthesis Example 5, 0.5 g of tetramethoxymethylglycoluril (manufactured by Nippon Cytec Industries, Inc., trade name: Powderlink [registered trademark] 1174) and pyridinium-p-toluenesulfonate 0.03 g was mixed and dissolved in 34.5 g of propylene glycol monomethyl ether and 18.2 g of ethyl lactate to obtain a solution. Then, it filtered using the polyethylene micro filter with the hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition.
- tetramethoxymethylglycoluril manufactured by Nippon Cytec Industries, Inc., trade name: Powderlink [registered trademark] 1174
- pyridinium-p-toluenesulfonate 0.03 g was
- a resist underlayer film forming composition containing a copolymer represented by the following formula (26) as a polymer and further containing a crosslinking agent represented by the following formula (27) and pyridinium-p-toluenesulfonate as an additive is prepared. did.
- a commercially available resist solution (manufactured by Dow Chemical Company, trade name: UV113) was applied to the upper layer of the resist underlayer film using a spinner.
- a resist film was formed by heating at 120 ° C. for 1 minute on a hot plate, and after exposure using an exposure apparatus, post-exposure heating (PEB: Post Exposure Bake) was performed at 115 ° C. for 1.5 minutes. After developing and rinsing the resist film, the thickness of the resist underlayer film is measured, and the resist underlayer film obtained from the resist underlayer film forming composition prepared in Examples 1 to 3 and the resist film It was confirmed that no intermixing occurred.
- PEB Post Exposure Bake
- a resist solution (manufactured by Sumitomo Chemical Co., Ltd., trade name: PAR710) was applied onto a silicon wafer using a spinner, and a resist film was formed by the same method as described above.
- the dry etching rate was measured using RIE system ES401 manufactured by Nippon Scientific Co., Ltd. under the condition using CF 4 as the dry etching gas.
- Table 1 shows the ratio of the dry etching rate of the resist underlayer film to the dry etching rate of the resist film (selection ratio of the dry etching rate).
- the resist underlayer film obtained from the resist underlayer film forming composition of the present invention has a large dry etching rate selectivity with respect to the resist film, and has a higher dry etching rate selectivity than Comparative Example 1. Therefore, compared with the resist underlayer film of the comparative example, the resist underlayer film of the present invention can shorten the time required for removal by dry etching. Further, it is possible to suppress an undesirable phenomenon in which the thickness of the resist film on the resist underlayer film decreases with the removal of the resist underlayer film by dry etching.
- LER is measured by using a critical dimension scanning electron microscope (CD-SEM) to detect a pattern edge position two-dimensionally from the top and quantify the variation in the position as LER. Specifically, using the white band width detected by the CD-SEM, measure the line width of a portion of 70% of the height from the bottom of the pattern to the top surface by 400 points, take 3 ⁇ of that value and take LER. Value.
- CD-SEM critical dimension scanning electron microscope
- Example 2 As shown in Table 2, when the resist underlayer film forming composition prepared in Example 1 of the present invention was used, the LER value was small compared to Comparative Example 1, and the pattern dimensional accuracy in the manufacturing process was high. Was confirmed.
- the LER value is usually required to be 4.0 nm or less.
- “> 4.5” means that the LER value is greater than 4.5.
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Abstract
Description
で表される繰り返しの構造単位を有するリソグラフィー用レジスト下層膜形成組成物である。
で表される。
でも表される。上記X1が式(5)を表す場合、当該式(5)のカルボニル基は上記式(3)の窒素原子と結合する。
でも表される。
で表される少なくとも一種の化合物と下記式(8b):
で表される少なくとも一種の化合物との重付加反応生成物である。
で表される。
で表される。前記mが0を表す場合は、Yで表される置換基が存在しないことを意味する。
でも表される。
GPCカラム:Shodex〔登録商標〕・Asahipak〔登録商標〕(昭和電工(株))
カラム温度:40℃
溶媒:N,N-ジメチルホルムアミド(DMF)
流量:0.6ml/分
標準試料:ポリスチレン(東ソー(株))
ディテクター:RI
テレフタル酸ジグリシジルエステル(ナガセケムテックス(株)製、商品名:デナコール〔登録商標〕EX711)10.00g、ビスフェノールS4.38g、2,4-ジヒドロキシ安息香酸2.68g、及びエチルトリフェニルホスホニウムブロミド0.65gをプロピレングリコールモノメチルエーテル70.90gに溶解させた後、130℃で4時間反応させポリマーの溶液を得た。得られたポリマーは、前記式(22)に相当し(a:b:c=10:5:5(モル比))、GPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量5,300であった。
テレフタル酸ジグリシジルエステル(ナガセケムテックス(株)製、商品名:デナコール〔登録商標〕EX711)10.00g、ビスフェノールS2.63g、2,4-ジヒドロキシ安息香酸3.78g、及びエチルトリフェニルホスホニウムブロミド0.65gをプロピレングリコールモノメチルエーテル68.21gに溶解させた後、130℃で4時間反応させポリマーの溶液を得た。得られたポリマーは、前記式(22)に相当し(a:b:c=10:3:7(モル比))、GPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量4,800であった。
テレフタル酸ジグリシジルエステル(ナガセケムテックス(株)製、商品名:デナコール〔登録商標〕EX711)10.00g、ビスフェノールS6.13g、2,4-ジヒドロキシ安息香酸1.62g、及びエチルトリフェニルホスホニウムブロミド0.65gをプロピレングリコールモノメチルエーテル73.60gに溶解させた後、130℃で4時間反応させポリマーの溶液を得た。得られたポリマーは、前記式(22)に相当し(a:b:c=10:7:3(モル比))、GPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量4,800であった。
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)製)15.00g、ビスフェノールS7.46g、2,4-ジヒドロキシ安息香酸4.59g、及びエチルトリフェニルホスホニウムブロミド1.01gをプロピレングリコールモノメチルエーテル112.21gに溶解させた後、130℃で4時間反応させポリマーの溶液を得た。得られたポリマーのGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量4,500であった。
モノアリルジグリシジルイソシアヌル酸(四国化成工業(株)製)15.00g、ビスフェノールS4.47g、2,4-ジヒドロキシ安息香酸6.43g、及びエチルトリフェニルホスホニウムブロミド1.00gをプロピレングリコールモノメチルエーテル107.62gに溶解させた後、130℃で4時間反応させポリマーの溶液を得た。得られたポリマーのGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量5,000であった。
上記合成例1で得られたポリマー2gを含む溶液10gにテトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)製、商品名:パウダーリンク〔登録商標〕1174)0.5gとピリジニウム-p-トルエンスルホネート0.05gを混合し、プロピレングリコールモノメチルエーテル35.4g、及び乳酸エチル18.6gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、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ろ過して、レジスト下層膜形成組成物を調製した。
上記合成例2で得られたポリマー2gを含む溶液10gにテトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)製、商品名:パウダーリンク〔登録商標〕1174)0.5gとピリジニウム-p-トルエンスルホネート0.05gを混合し、プロピレングリコールモノメチルエーテル35.4g、及び乳酸エチル18.6gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、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ろ過して、レジスト下層膜形成組成物を調製した。
上記合成例3で得られたポリマー2gを含む溶液10gにテトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)製、商品名:パウダーリンク〔登録商標〕1174)0.5gとピリジニウム-p-トルエンスルホネート0.05gを混合し、プロピレングリコールモノメチルエーテル35.4g、及び乳酸エチル18.6gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、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ろ過して、レジスト下層膜形成組成物を調製した。
上記合成例4で得られたポリマー2gを含む溶液10gにテトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)製、商品名:パウダーリンク〔登録商標〕1174)0.5gとピリジニウム-p-トルエンスルホネート0.03gを混合し、プロピレングリコールモノメチルエーテル34.5g、及び乳酸エチル18.2gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、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ろ過して、レジスト下層膜形成組成物を調製した。
上記合成例5で得られたポリマー2gを含む溶液10gにテトラメトキシメチルグリコールウリル(日本サイテックインダストリーズ(株)製、商品名:パウダーリンク〔登録商標〕1174)0.5gとピリジニウム-p-トルエンスルホネート0.03gを混合し、プロピレングリコールモノメチルエーテル34.5g、及び乳酸エチル18.2gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いてろ過し、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ろ過して、レジスト下層膜形成組成物を調製した。
下記式(26)で表される共重合体をポリマーとして含み、さらに添加物として下記式(27)で表される架橋剤、及びピリジニウム-p-トルエンスルホネートを含むレジスト下層膜形成組成物を用意した。
本発明の実施例1乃至実施例5で調製したレジスト下層膜形成組成物を、スピナーを用いてシリコンウエハー上に塗布(スピンコート)した。ホットプレート上で、205℃で1分間加熱し、レジスト下層膜(膜厚0.10μm)を形成した。このレジスト下層膜を、レジスト溶液の溶剤である乳酸エチル及びプロピレングリコールモノメチルエーテルに浸漬し、前記レジスト下層膜はそれらの溶剤に不溶であることを確認した。
本発明の実施例1乃至実施例5で調製したレジスト下層膜形成組成物を、スピナーを用いてシリコンウエハー上に塗布した。ホットプレート上で、205℃で1分間加熱し、レジスト下層膜(膜厚0.10μm)を形成した。
本発明の実施例1乃至実施例5で調製したレジスト下層膜形成組成物、及び比較例1で示したレジスト下層膜形成組成物を、それぞれスピナーを用いてシリコンウエハー上に塗布した。ホットプレート上で、205℃で1分間加熱し、レジスト下層膜を形成した。そして、日本サイエンティフィック社製、RIEシステムES401を用い、ドライエッチングガスとしてCF4を使用した条件下でドライエッチング速度を測定した。
シリコンウエハー上に、本発明の実施例1で調製したレジスト下層膜形成組成物をそれぞれスピンコートし、205℃で1分間加熱し、レジスト下層膜を形成した。そのレジスト下層膜上に、EUV用レジスト溶液(メタクリレート樹脂系レジスト)をスピンコートし、加熱し、レジスト膜を形成した。EUV露光装置(ASML社製EUV-ADT)を用いて、NA=0.25、σ=0.5の条件で露光した。露光後、PEBを行い、クーリングプレート上で室温まで冷却し、現像及びリンス処理をし、レジストパターンを形成した。評価は、30nmのラインアンドスペースの形成可否、パターン上面からの観察によるパターンのラインエッジラフネス(LER)の大小により行った。
Claims (16)
- ポリマー及び溶剤を含み、前記ポリマーはジフェニルスルホンまたはその誘導体がエーテル結合を介して該ポリマーの主鎖に導入されている、リソグラフィー用レジスト下層膜形成組成物。
- 前記式(1b)において、Qは下記式(3):
で表される請求項2に記載のリソグラフィー用レジスト下層膜形成組成物。 - 架橋性化合物をさらに含む請求項1乃至請求項10のいずれか一項に記載のリソグラフィー用レジスト下層膜形成組成物。
- 架橋反応を促進させる化合物をさらに含む請求項11に記載のリソグラフィー用レジスト下層膜形成組成物。
- 前記架橋性化合物はメチロール基またはアルコキシメチル基で置換された窒素原子を2つ乃至4つ有する含窒素化合物である請求項11に記載のリソグラフィー用レジスト下層膜形成組成物。
- 前記架橋反応を促進させる化合物はスルホン酸化合物及び熱酸発生剤から選ばれる少なくとも一種である請求項12に記載のリソグラフィー用レジスト下層膜形成組成物。
- 請求項1乃至請求項14のいずれか一項に記載のリソグラフィー用レジスト下層膜形成組成物を半導体基板上に塗布しベークしてレジスト下層膜を形成する工程、前記レジスト下層膜上にレジスト膜を形成する工程、前記レジスト下層膜と前記レジスト膜で被覆された半導体基板を露光する工程、露光後に前記レジスト膜を現像する工程、を含む半導体装置の製造に用いるレジストパターンの形成方法。
- 前記露光は極端紫外線を用いて行われる請求項15に記載のレジストパターンの形成方法。
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JP6521263B2 (ja) * | 2014-10-21 | 2019-05-29 | 日産化学株式会社 | レジスト下層膜形成組成物 |
KR102421597B1 (ko) * | 2015-07-14 | 2022-07-18 | 에스케이이노베이션 주식회사 | 신규한 레지스트 하층막 형성용 중합체, 이를 포함하는 레지스트 하층막 형성용 조성물 및 이를 이용한 레지스트 패턴의 형성 방법 |
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