WO2012124597A1 - 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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- WO2012124597A1 WO2012124597A1 PCT/JP2012/055963 JP2012055963W WO2012124597A1 WO 2012124597 A1 WO2012124597 A1 WO 2012124597A1 JP 2012055963 W JP2012055963 W JP 2012055963W WO 2012124597 A1 WO2012124597 A1 WO 2012124597A1
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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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4223—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aromatic
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- 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
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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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
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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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
Definitions
- the present invention provides a resist underlayer film forming composition for lithography and a resist that can form a uniform film without defects even when a resist underlayer film having a thin film thickness (for example, 20 nm or less) is formed.
- the present invention relates to a resist pattern forming method using an underlayer film forming composition.
- microfabrication forms a thin film of a photoresist composition on a semiconductor substrate such as a silicon wafer, and irradiates with an actinic ray such as ultraviolet rays through a mask pattern on which a device pattern is drawn, and develops it.
- This is a processing method for forming fine irregularities corresponding to the pattern on the substrate surface by etching the substrate using the obtained photoresist pattern as a protective film.
- Patent Documents 1 to 3 there is no intermixing with the photoresist film formed on the upper layer, and when exposure is performed using an ArF excimer laser, desired optical parameters (k value, n value) are obtained, and A resist underlayer film (antireflection film) capable of obtaining a desired dry etching rate is disclosed.
- the characteristics required for the resist lower layer film include, for example, that no intermixing with the resist film formed in the upper layer occurs (insoluble in the resist solvent), and a higher dry etching rate than the resist film. Is mentioned.
- the pattern line width to be formed is 32 nm or less, and the resist underlayer film for EUV exposure is used with a thinner film thickness than in the past.
- the resist underlayer film for EUV exposure is used with a thinner film thickness than in the past.
- An object of the present invention is to obtain a composition for forming a resist underlayer film that can form a desired resist pattern by solving the above problems.
- a first aspect of the present invention is a resist underlayer film forming composition for lithography comprising a polymer having a structure represented by the following formula (1) at the end of a polymer chain, a crosslinking agent, a compound for promoting a crosslinking reaction, and an organic solvent. It is.
- R 1, R 2 and R 3 are each independently a hydrogen atom, a linear or branched hydrocarbon group having a carbon number of 1 to 13, or a hydroxy group, wherein R 1, R 2 And at least one of R 3 is the hydrocarbon group, m and n each independently represents 0 or 1, the main chain of the polymer is bonded to a methylene group when n is 1, and n is 0. When represented, it is bonded to the group represented by —O—.
- a resist underlayer film forming composition for lithography of the present invention is applied on a semiconductor substrate and baked to form a resist underlayer film having a thickness of 1 nm to 20 nm, on the resist underlayer film Forming a resist film, exposing the semiconductor substrate coated with the resist underlayer film and the resist film with radiation selected from the group consisting of KrF excimer laser, ArF excimer laser, extreme ultraviolet (EUV), and electron beam
- the present invention relates to a resist pattern forming method including a step of developing with an alkaline developer after exposure.
- the resist underlayer film forming composition for lithography of the present invention is characterized in that a polymer terminal contained in the resist underlayer film forming composition is capped with a structure represented by the formula (1). And a composition containing such a polymer, a crosslinking agent, a compound for promoting a crosslinking reaction, and an organic solvent. With such a configuration, the coating performance is improved, and a uniform resist underlayer film having no defects can be formed.
- FIG. 2 is an FE-SEM image of a resist underlayer film formed using the composition prepared in Example 1.
- FIG. 2 is an FE-SEM image of a resist underlayer film formed using the composition prepared in Example 2.
- FIG. 4 is an FE-SEM image of a resist underlayer film formed using the composition prepared in Example 3.
- FIG. 6 is an FE-SEM image of a resist underlayer film formed using the composition prepared in Example 4.
- 2 is an FE-SEM image of a resist underlayer film formed using the composition prepared in Comparative Example 1.
- 3 is an FE-SEM image of a resist underlayer film formed using the composition prepared in Comparative Example 2.
- the polymer contained in the resist underlayer film forming composition for lithography of the present invention has a structure represented by the formula (1) at the end of the polymer chain.
- at least one of R 1 , R 2 and R 3 is a linear or branched hydrocarbon group having 1 to 13 carbon atoms.
- the hydrocarbon group is preferably an alkyl group such as a tert-butyl group, an iso-propyl group, or a methyl group from the viewpoint of improving the solubility of the polymer and the coating property of the composition.
- a propyl group is particularly preferred.
- the said polymer has a structural unit represented, for example by following formula (2) and Formula (3).
- Q 1 and Q 2 are each independently a divalent organic group having a linear or branched hydrocarbon group having 1 to 13 carbon atoms, or a divalent group having an alicyclic hydrocarbon group.
- the structural unit represented by the above formula (2) is represented, for example, by the following formula (2 ′).
- Q 3 represents a linear or branched hydrocarbon group, alicyclic hydrocarbon group or aromatic ring having 1 to 13 carbon atoms, and the hydrocarbon group and the alicyclic hydrocarbon group.
- the aromatic ring may have at least one substituent, and two v's independently represent 0 or 1.
- the hydrocarbon group, the alicyclic hydrocarbon group and the aromatic ring may have at least one methyl group, hydroxy group or fluoro group as a substituent.
- the structural unit represented by the above formula (3) is represented by the following formula (3 ′), for example.
- Q 4 represents a linear or branched hydrocarbon group having 1 to 13 carbon atoms, an alicyclic hydrocarbon group or an aromatic ring, and the hydrocarbon group and the alicyclic hydrocarbon group.
- the aromatic ring may have at least one substituent, and the hydrocarbon group may have one or two sulfur atoms in the main chain, and may have a double bond.
- two w's each independently represent 0 or 1.
- Examples of the substituent of the linear or branched hydrocarbon group include a hydroxy group and a fluoro group.
- substituent on the alicyclic hydrocarbon group, the aromatic ring, and the heterocyclic ring include a methyl group, an ethyl group, a tert-butyl group, an allyl group, a hydroxy group, and a fluoro group.
- Examples of the alicyclic hydrocarbon group include a cyclobutylene group, a cyclopentylene group, and a cyclohexylene group.
- the aromatic ring include a benzene ring, a naphthalene ring, and an anthracene ring.
- heterocyclic ring include a triazine trione ring, a pyrimidine trione ring, an imidazolidinedione ring, an imidazolidone ring, and a pyridone ring.
- Examples of the monomer that forms the structure represented by the formula (1) include compounds represented by the following formulas (1-1) to (1-9).
- Examples of the monomer that forms the structural unit represented by the formula (2) include compounds having two epoxy groups represented by the following formulas (2-1) to (2-16). it can.
- Examples of the monomer that forms the structural unit represented by the formula (3) include compounds represented by the following formulas (3-1) to (3-10).
- the polymer contained in the resist underlayer film forming composition for lithography of the present invention is represented, for example, by the following formula (4).
- R 1 , R 2 and R 3 have the same meanings as those in the formula (1), two m and two n each independently represent 0 or 1, and X represents the formula (2) and the formula ( 3 represents a polymer chain having the structural unit represented by 3)
- the above formula (4) represents that the end of the polymer chain is capped by the structure represented by the formula (1).
- the monomer that forms the structure represented by the formula (1) necessary for obtaining the polymer represented by the formula (4) forms the structural unit represented by the formula (2) and the formula (3).
- the total amount of monomers is 100% by mass, for example, it is 1% by mass to 30% by mass (in terms of monomer charge ratio), and preferably 2% by mass to 20% by mass.
- the polymer contained in the resist underlayer film forming composition for lithography of the present invention may be any of a random copolymer, a block copolymer, an alternating copolymer, and a graft copolymer.
- a polymer polymerization method various methods such as solution polymerization, suspension polymerization, emulsion polymerization, and bulk polymerization are possible, and a polymerization catalyst or the like may be appropriately used.
- the monomer that forms the structural unit represented by the formula (2) and the monomer that forms the structural unit represented by the formula (3) are represented by the formula (1). It can be synthesized by adding a monomer for forming the structure and a polymerization catalyst and performing thermal polymerization.
- the organic solvent used here can be suitably selected from the preferable examples as the organic solvent contained in the resist underlayer film forming composition for lithography of the present invention described later.
- the polymerization catalyst include benzyltriethylammonium chloride and ethyltriphenylphosphonium bromide.
- the polymerization can be performed by heating to 50 ° C to 160 ° C, preferably 70 ° C to 130 ° C.
- the reaction time is, for example, 1 hour to 50 hours, preferably 2 hours to 12 hours.
- the weight average molecular weight of the polymer is, for example, 1000 to 100,000, preferably 1000 to 10,000. When the value of this weight average molecular weight is too high, the applicability of the resist underlayer film forming composition for lithography of the present invention deteriorates.
- the resist underlayer film forming composition for lithography of the present invention is 100% by mass, the polymer contained in the composition is, for example, 0.01% by mass to 3% by mass, preferably 0.1% by mass to 2% by mass. It is.
- the weight average molecular weight is a value obtained by using gel as a standard sample by gel permeation chromatography (GPC).
- the resist underlayer film forming composition for lithography of the present invention further contains a crosslinking agent.
- a crosslinking agent there is no restriction
- crosslinking formation substituents for example, a methylol group, a methoxymethyl group, a butoxymethyl group is used preferably.
- crosslinking agent examples 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, 1,1,3,3- Tetrakis (methoxymethyl) urea is mentioned.
- the crosslinking agent contained in the resist underlayer film forming composition for lithography of the present invention is, for example, 1% by mass to 100% by mass, preferably 10% by mass to 50% by mass, when the polymer in the composition is 100% by mass. It is.
- These crosslinking agents may cause a crosslinking reaction by self-condensation, but are structural units represented by the formulas (2) and (3) which are structural units that react with the polymer, particularly the crosslinking agent to form a crosslinking. It is possible to cause a crosslinking reaction with a crosslinking functional group (hydroxy group) therein.
- the resist underlayer film forming composition for lithography of the present invention further contains a compound that promotes the crosslinking reaction.
- a compound that promotes the crosslinking reaction examples include p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium-p-toluenesulfonate, salicylic acid, camphorsulfonic acid, 5-sulfosalicylic acid, 4-chlorobenzenesulfonic acid, 4-hydroxybenzenesulfone.
- Acid benzenedisulfonic acid, 1-naphthalenesulfonic acid, citric acid, benzoic acid, hydroxybenzoic acid and other sulfonic acid compounds and carboxylic acid compounds can be used. These compounds that accelerate the crosslinking reaction can be used alone or in combination of two or more.
- the compound that promotes the crosslinking reaction contained in the resist underlayer film forming composition for lithography of the present invention is, for example, 0.1% by mass to 25% by mass, preferably 1%, assuming that the polymer in the composition is 100% by mass. Mass% to 10 mass%.
- the resist underlayer film forming composition for lithography of the present invention further contains an organic solvent.
- the organic solvent used in the present invention is not particularly limited as long as it can dissolve the aforementioned polymer.
- organic solvents propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 1-ethoxy-2-propanol, ethyl lactate, butyl lactate, and cyclohexanone are preferable.
- the organic solvent contained in the resist underlayer film forming composition for lithography of the present invention is, for example, 90% by mass to 99.99% by mass, preferably 98% by mass to 99.9% by mass, assuming that the composition is 100% by mass. %.
- the resist underlayer film forming composition for lithography of the present invention may further contain an acid generator.
- an acid generator include bis (4-hydroxyphenyl) sulfone.
- the resist underlayer film forming composition for lithography of the present invention contains the acid generator, for example, 0.1% by mass to 5% by mass, preferably 0.2% by mass, when the polymer in the composition is 100% by mass. % To 3% by mass.
- the composition for forming a resist underlayer film for lithography of the present invention may further contain various additives such as a surfactant as necessary as long as the effects of the present invention are not impaired.
- the surfactant is an additive for improving the applicability of the composition to the substrate.
- Known surfactants such as nonionic surfactants and fluorine surfactants can be used.
- the surfactant include, for example, polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, Polyoxyethylene alkyl aryl ethers such as polyoxyethylene nonylphenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, Sorbitan fatty acid esters such as sorbitan tristearate, polyoxyethylene sorbitan monolaurate, poly Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as xylethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbititan
- the resist underlayer film forming composition for lithography of the present invention contains the above surfactant, for example, when the polymer in the composition is 100% by mass, it is 0.1% by mass to 5% by mass, preferably 0.8%. 2 to 3% by mass is contained.
- a substrate used in the manufacture of a precision integrated circuit element for example, a semiconductor substrate such as a silicon wafer coated with a silicon oxide film, a silicon nitride film or a silicon oxynitride film, a silicon nitride substrate, a quartz substrate, a glass substrate (no (Including alkali glass, low alkali glass, crystallized glass), glass substrate on which an ITO film is formed) by applying a resist underlayer film forming composition for lithography of the present invention on a glass substrate on which an ITO film is formed by an appropriate coating method such as a spinner or coater, Thereafter, the resist underlayer film is produced by baking and curing using a heating means such as a hot plate.
- a heating means such as a hot plate.
- the conditions for baking after coating are appropriately selected from the range of, for example, a baking temperature of 80 to 250 ° C. and a baking time of 0.3 to 60 minutes, and preferably 150 to 250 ° C. and 0.5 to 5 minutes. It is.
- a crosslinking structure such as a hydroxyl group in the structural unit of the polymer reacts with a crosslinking agent to form a crosslinked structure.
- the crosslinking density of the crosslinked polymer can be increased by crosslinking the polymer contained in the resist underlayer film forming composition for lithography of the present invention.
- the thickness of the resist underlayer film is, for example, 0.001 ⁇ m (1 nm) to 0.1 ⁇ m, preferably 0.001 ⁇ m to 0.02 ⁇ m, and more preferably 0.003 ⁇ m to 0.01 ⁇ m.
- the resist film can be formed by a general method, that is, by applying a resist solution onto the resist underlayer film and baking.
- the resist solution to be applied is not particularly limited as long as it is sensitive to, for example, KrF excimer laser, ArF excimer laser, EUV, or electron beam, and either negative type or positive type can be used.
- Usable resist solutions include, for example, Sumitomo Chemical Co., Ltd .; trade names PAR710, PAR855, JSR Corporation; trade names AR2772JN, Shin-Etsu Chemical Co., Ltd .; trade names SEPR430, Dow Chemical Co., Ltd. (Formerly Rohm and Haas Electronic Materials); trade name APEX-X.
- the resist film formed on the upper layer of the resist lower layer film is exposed through a predetermined mask (reticle).
- a predetermined mask for the exposure, for example, a KrF excimer laser, an ArF excimer laser, or EUV can be used. However, in the case of electron beam exposure, a mask (reticle) is not required.
- post-exposure heating PEB: Post Exposure Bake
- the conditions for the post-exposure heating are appropriately selected from the range of a heating temperature of 80 ° C. to 150 ° C. and a heating time of 0.3 minutes to 60 minutes.
- a good resist pattern can be obtained by developing, rinsing and drying.
- alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, inorganic alkalis such as aqueous ammonia, and primary amines such as ethylamine and n-propylamine are used.
- Secondary amines such as amines, diethylamine and di-n-butylamine, tertiary amines such as triethylamine and methyldiethylamine, alcohol amines such as dimethylethanolamine and triethanolamine, tetramethylammonium hydroxide, tetraethyl
- An aqueous solution of a quaternary ammonium salt such as ammonium hydroxide or choline, or a cyclic amine such as pyrrole or piperidine can be used.
- an appropriate amount of an alcohol such as isopropyl alcohol or a nonionic surfactant may be added to the alkaline aqueous solution.
- a preferred developer is an aqueous solution of a quaternary ammonium salt, more preferably an aqueous solution of tetramethylammonium hydroxide.
- the development conditions are appropriately selected from the range of a development temperature of 5 ° C. to 50 ° C. and a development time of 10 seconds to 300 seconds.
- the resist underlayer film exposed by developing and removing the resist film by the above process is removed by dry etching, and a desired pattern can be formed on the substrate.
- the weight average molecular weights shown in the following Synthesis Examples 1 to 6 in the present specification are measurement results by gel permeation chromatography (hereinafter abbreviated as GPC in the present specification).
- GPC gel permeation chromatography
- a GPC apparatus manufactured by Tosoh Corporation is used, and the measurement conditions are as follows.
- the dispersity shown in the following synthesis examples of the present specification was calculated from the measured weight average molecular weight and number average molecular weight.
- the polymer solution did not cause white turbidity or the like even when cooled to room temperature, and had good solubility in propylene glycol monomethyl ether.
- the polymer in the obtained solution had a weight average molecular weight of 6066 and a dispersity of 2.64 in terms of standard polystyrene.
- the polymer solution did not cause white turbidity or the like even when cooled to room temperature, and had good solubility in propylene glycol monomethyl ether.
- the polymer in the obtained solution had a weight average molecular weight of 4746 and a dispersity of 2.68 in terms of standard polystyrene.
- the polymer solution did not cause white turbidity or the like even when cooled to room temperature, and had good solubility in propylene glycol monomethyl ether.
- the polymer in the obtained solution had a weight average molecular weight of 5634 in terms of standard polystyrene and a dispersity of 2.70.
- the polymer solution did not cause white turbidity or the like even when cooled to room temperature, and had good solubility in propylene glycol monomethyl ether.
- the polymer in the obtained solution had a weight average molecular weight of 4669 in terms of standard polystyrene and a dispersity of 2.50.
- the polymer solution did not cause white turbidity or the like even when cooled to room temperature, and had good solubility in propylene glycol monomethyl ether.
- the polymer in the obtained solution had a weight average molecular weight of 5745 and a dispersity of 2.67 in terms of standard polystyrene.
- Example 1 To 0.4 g of a solution containing 0.07 g of the polymer obtained in Synthesis Example 1 above, tetramethoxymethylglycoluril (manufactured by Nippon Cytec Industries [former Mitsui Cytec Co., Ltd., trade name: POWDERLINK [registered trademark] 1174). 0184 g and 5-sulfosalicylic acid 0.0018 g were mixed, and propylene glycol monomethyl ether 21.27 g and 1-ethoxy-2-propanol 9.33 g were added and dissolved. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist underlayer film forming composition for lithography.
- tetramethoxymethylglycoluril manufactured by Nippon Cytec Industries [former Mitsui Cytec Co., Ltd., trade name: POWDERLINK [registered trademark] 1174. 0184 g and 5-sulfosal
- Example 2 To 0.4 g of a solution containing 0.07 g of the polymer obtained in Synthesis Example 2 above, tetramethoxymethylglycoluril (manufactured by Nippon Cytec Industries [former Mitsui Cytec], trade name: POWDERLINK [registered trademark] 1174). 0184 g and 5-sulfosalicylic acid 0.0018 g were mixed, and propylene glycol monomethyl ether 21.27 g and 1-ethoxy-2-propanol 9.33 g were added and dissolved. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist underlayer film forming composition for lithography.
- tetramethoxymethylglycoluril manufactured by Nippon Cytec Industries [former Mitsui Cytec], trade name: POWDERLINK [registered trademark] 1174. 0184 g and 5-sulfosalicylic acid 0.0018 g were mixed
- Example 3 To 0.4 g of a solution containing 0.07 g of the polymer obtained in Synthesis Example 3, tetramethoxymethylglycoluril (manufactured by Nippon Cytec Industries [former Mitsui Cytec Co., Ltd., trade name: POWDERLINK [registered trademark] 1174) 0184 g and 5-sulfosalicylic acid 0.0018 g were mixed, and propylene glycol monomethyl ether 21.27 g and 1-ethoxy-2-propanol 9.33 g were added and dissolved. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist underlayer film forming composition for lithography.
- tetramethoxymethylglycoluril manufactured by Nippon Cytec Industries [former Mitsui Cytec Co., Ltd., trade name: POWDERLINK [registered trademark] 1174
- Example 4 To 0.4 g of a solution containing 0.07 g of the polymer obtained in Synthesis Example 4 above, tetramethoxymethylglycoluril (manufactured by Nippon Cytec Industries [former Mitsui Cytec], trade name: POWDERLINK [registered trademark] 1174). 0184 g and 5-sulfosalicylic acid 0.0018 g were mixed, and propylene glycol monomethyl ether 21.27 g and 1-ethoxy-2-propanol 9.33 g were added and dissolved. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to obtain a resist underlayer film forming composition for lithography.
- tetramethoxymethylglycoluril manufactured by Nippon Cytec Industries [former Mitsui Cytec], trade name: POWDERLINK [registered trademark] 1174. 0184 g and 5-sulfosalicylic acid 0.0018 g were mixed
- the resist underlayer film forming compositions prepared in Examples 1 to 4 and Comparative Example 3 were each applied onto a silicon wafer using a spinner.
- the silicon wafer was placed on a hot plate and baked at 205 ° C. for 1 minute to form a resist underlayer film (film thickness: 0.10 ⁇ m).
- the dry etching rate was measured using RIE system ES401 manufactured by Nippon Scientific.
- the dry etching rate selection ratio (resist underlayer film / resist film) of the coating type resist underlayer film of the present invention with respect to the resist film was measured using CF 4 gas as an etching gas.
- the resist underlayer film obtained from the resist underlayer film forming composition of each example has a higher dry etching rate selectivity than the resist underlayer film obtained from the resist underlayer film forming composition of Comparative Example 3. It was.
- FIG. 1 to FIG. 6 show SEM images when the resist underlayer film formed using the compositions prepared in each Example and each Comparative Example is observed from above using the FE-SEM.
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Abstract
Description
本発明のリソグラフィー用レジスト下層膜形成組成物に含まれるポリマーは、前記式(1)で表される構造をポリマー鎖の末端に有する。該式(1)中、R1、R2及びR3の少なくとも1つは炭素原子数1乃至13の直鎖状若しくは分岐鎖状の炭化水素基である。該炭化水素基としてアルキル基、例えば、tert-ブチル基、iso-プロピル基、メチル基がポリマーの溶解性及び組成物の塗布性を向上させる点で好ましく、これらのうちtert-ブチル基及びiso-プロピル基が特に好ましい。
前記炭化水素基、前記脂環式炭化水素基及び前記芳香環は置換基として、メチル基、ヒドロキシ基又はフルオロ基を少なくとも1つ有していてもよい。
さらに、上記式(3)で表される構造単位は、例えば下記式(3´)で表される。
上記式(4)は、前記式(1)で表される構造によって、上記ポリマー鎖の末端がキャッピングされていることを表している。
なお、重量平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)により、標準試料としてポリスチレンを用いて得られる値である。
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、さらに架橋剤を含む。その架橋剤として、特に制限はないが、少なくとも二つの架橋形成置換基(例えば、メチロール基、メトキシメチル基、ブトキシメチル基)を有する含窒素化合物が好ましく用いられる。
架橋反応を促進させるために、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、さらに架橋反応を促進させる化合物を含む。そのような化合物としては、例えば、p-トルエンスルホン酸、トリフルオロメタンスルホン酸、ピリジニウム-p-トルエンスルホナート、サリチル酸、カンファースルホン酸、5-スルホサリチル酸、4-クロロベンゼンスルホン酸、4-ヒドロキシベンゼンスルホン酸、ベンゼンジスルホン酸、1-ナフタレンスルホン酸、クエン酸、安息香酸、ヒドロキシ安息香酸等のスルホン酸化合物及びカルボン酸化合物を使用できる。これら架橋反応を促進させる化合物は、一種のみを使用することができ、また、二種以上を組み合わせて用いることもできる。本発明のリソグラフィー用レジスト下層膜形成組成物に含まれる上記架橋反応を促進させる化合物は、当該組成物中のポリマーを100質量%とすると、例えば0.1質量%乃至25質量%、好ましくは1質量%乃至10質量%である。
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さらに有機溶媒を含む。本発明において使用される有機溶媒としては、前述のポリマーを溶解することができれば特に制限されず、例えば、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、メチルセロソルブアセテート、エチルセロソルブアセテート、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノプロピルエーテル、1-エトキシ-2-プロパノール、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールプロピルエーテルアセテート、1-メトキシ-2-ブタノール、2-メトキシ-1-ブタノール、3-メトキシ-3-メチルブタノール、3-メトキシ-1-ブタノール、トルエン、キシレン、メチルエチルケトン、シクロペンタノン、シクロヘキサノン、γ-ブチロラクトン、N-メチル-2-ピロリドン、2-ヒドロキシイソ酪酸メチル、2-ヒドロキシプロピオン酸エチル、2-ヒドロキシ-2-メチルプロピオン酸エチル、エトキシ酢酸エチル、ヒドロキシ酢酸エチル、2-ヒドロキシ-3-メチルブタン酸メチル、3-メトキシプロピオン酸メチル、3-メトキシプロピオン酸エチル、3-エトキシプロピオン酸エチル、3-エトキシプロピオン酸メチル、ピルビン酸メチル、ピルビン酸エチル、酢酸エチル、酢酸ブチル、乳酸エチル、乳酸ブチル、を用いることができる。これらの有機溶媒は単独で、又は2種以上の組合せで使用される。
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さらに酸発生剤を含んでいてもよい。そのような酸発生剤としては、例えば、ビス(4-ヒドロキシフェニル)スルホンが挙げられる。本発明のリソグラフィー用レジスト下層膜形成組成物が上記酸発生剤を含む場合、当該組成物中のポリマーを100質量%とすると、例えば0.1質量%乃至5質量%、好ましくは0.2質量%乃至3質量%含む。
本発明のリソグラフィー用レジスト下層膜形成組成物には、必要に応じて界面活性剤等の各種添加剤を、本発明の効果を損なわない限りにおいてさらに含んでもよい。界面活性剤は、基板に対する当該組成物の塗布性を向上させるための添加物である。ノニオン系界面活性剤、フッ素系界面活性剤のような公知の界面活性剤を用いることができる。
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(東ソー株式会社製)
ディテクター:RIディテクター(東ソー株式会社製、RI-8020)
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式会社製、商品名:デナコール〔登録商標〕EX711)5g、5-ヒドロキシイソフタル酸3.146g、3,5-ジ-tert-ブチルサリチル酸水和物0.562g及びベンジルトリエチルアンモニウムクロリド0.199gを、プロピレングリコールモノメチルエーテル35.6gに加え溶解させた。反応容器を窒素置換後、135℃で4時間反応させ、ポリマー溶液を得た。当該ポリマー溶液は、室温に冷却しても白濁等を生じることはなく、プロピレングリコールモノメチルエーテルに対する溶解性は良好であった。GPC分析を行ったところ、得られた溶液中のポリマーは、標準ポリスチレン換算にて重量平均分子量6066、分散度は2.64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式会社製、商品名:デナコール〔登録商標〕EX711)5g、5-ヒドロキシイソフタル酸3.146g、3,5-ジ-tert-ブチルサリチル酸水和物0.864g及びベンジルトリエチルアンモニウムクロリド0.197gを、プロピレングリコールモノメチルエーテル36.8gに加え溶解させた。反応容器を窒素置換後、135℃で4時間反応させ、ポリマー溶液を得た。当該ポリマー溶液は、室温に冷却しても白濁等を生じることはなく、プロピレングリコールモノメチルエーテルに対する溶解性は良好であった。GPC分析を行ったところ、得られた溶液中のポリマーは、標準ポリスチレン換算にて重量平均分子量4746、分散度は2.68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式会社製、商品名:デナコール〔登録商標〕EX711)5g、5-ヒドロキシイソフタル酸3.146g、3,5-ジイソプロピルサリチル酸水和物0.575g及びベンジルトリエチルアンモニウムクロリド0.197gを、プロピレングリコールモノメチルエーテル35.7gに加え溶解させた。反応容器を窒素置換後、135℃で4時間反応させ、ポリマー溶液を得た。当該ポリマー溶液は、室温に冷却しても白濁等を生じることはなく、プロピレングリコールモノメチルエーテルに対する溶解性は良好であった。GPC分析を行ったところ、得られた溶液中のポリマーは、標準ポリスチレン換算にて重量平均分子量5634、分散度は2.70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式会社製、商品名:デナコール〔登録商標〕EX711)5g、5-ヒドロキシイソフタル酸3.146g、3,5-ジイソプロピルサリチル酸水和物0.767g及びベンジルトリエチルアンモニウムクロリド0.197gを、プロピレングリコールモノメチルエーテル35.7gに加え溶解させた。反応容器を窒素置換後、135℃で4時間反応させ、ポリマー溶液を得た。当該ポリマー溶液は、室温に冷却しても白濁等を生じることはなく、プロピレングリコールモノメチルエーテルに対する溶解性は良好であった。GPC分析を行ったところ、得られた溶液中のポリマーは、標準ポリスチレン換算にて重量平均分子量4669、分散度は2.50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式会社製、商品名:デナコール〔登録商標〕EX711)5g、5-ヒドロキシイソフタル酸3.146g及びベンジルトリエチルアンモニウムクロリド0.202gを、プロピレングリコールモノメチルエーテル35.6gに加え溶解させた。反応容器を窒素置換後、135℃で4時間反応させ、ポリマー溶液を得た。当該ポリマー溶液は、室温に冷却しても白濁を生じることはなく、プロピレングリコールモノメチルエーテルに対する溶解性は良好であった。GPC分析を行ったところ、得られた溶液中のポリマーは、標準ポリスチレン換算にて重量平均分子量15673、分散度は3.39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式会社製、商品名:デナコール〔登録商標〕EX711)5g、5-ヒドロキシイソフタル酸3.146g、サリチル酸0.357g及びベンジルトリエチルアンモニウムクロリド0.202gを、プロピレングリコールモノメチルエーテル37.5gに加え溶解させた。反応容器を窒素置換後、135℃で4時間反応させ、ポリマー溶液を得た。当該ポリマー溶液は、室温に冷却しても白濁等を生じることはなく、プロピレングリコールモノメチルエーテルに対する溶解性は良好であった。GPC分析を行ったところ、得られた溶液中のポリマーは、標準ポリスチレン換算にて重量平均分子量5745、分散度は2.67であった。
上記合成例1で得られたポリマー0.07gを含む溶液0.4g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〔旧三井サイテック〕株式会社製、商品名:POWDERLINK〔登録商標〕1174)0.0184g及び5-スルホサリチル酸0.0018gを混合し、プロピレングリコールモノメチルエーテル21.27g及び1-エトキシ-2-プロパノール9.33gを加え溶解させた。その後孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して、リソグラフィー用レジスト下層膜形成組成物とした。
上記合成例2で得られたポリマー0.07gを含む溶液0.4g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〔旧三井サイテック〕株式会社製、商品名:POWDERLINK〔登録商標〕1174)0.0184g及び5-スルホサリチル酸0.0018gを混合し、プロピレングリコールモノメチルエーテル21.27g及び1-エトキシ-2-プロパノール9.33gを加え溶解させた。その後孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して、リソグラフィー用レジスト下層膜形成組成物とした。
上記合成例3で得られたポリマー0.07gを含む溶液0.4g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〔旧三井サイテック〕株式会社製、商品名:POWDERLINK〔登録商標〕1174)0.0184g及び5-スルホサリチル酸0.0018gを混合し、プロピレングリコールモノメチルエーテル21.27g及び1-エトキシ-2-プロパノール9.33gを加え溶解させた。その後孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して、リソグラフィー用レジスト下層膜形成組成物とした。
上記合成例4で得られたポリマー0.07gを含む溶液0.4g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〔旧三井サイテック〕株式会社製、商品名:POWDERLINK〔登録商標〕1174)0.0184g及び5-スルホサリチル酸0.0018gを混合し、プロピレングリコールモノメチルエーテル21.27g及び1-エトキシ-2-プロパノール9.33gを加え溶解させた。その後孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して、リソグラフィー用レジスト下層膜形成組成物とした。
上記合成例5で得られたポリマー0.07gを含む溶液0.4g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〔旧三井サイテック〕株式会社製、商品名:POWDERLINK〔登録商標〕1174)0.0184g、5-スルホサリチル酸0.0018gを混合し、プロピレングリコールモノメチルエーテル21.27g及び1-エトキシ-2-プロパノール9.33gを加え溶解させた。その後孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して、リソグラフィー用レジスト下層膜形成組成物とした。
上記合成例6で得られたポリマー0.07gを含む溶液0.4g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〔旧三井サイテック〕株式会社製、商品名:POWDERLINK〔登録商標〕1174)0.0184g及び5-スルホサリチル酸0.0018gを混合し、プロピレングリコールモノメチルエーテル21.27g及び1-エトキシ-2-プロパノール9.33gを加え溶解させた。その後孔径0.05μmのポリエチレン製ミクロフィルターを用いてろ過して、リソグラフィー用レジスト下層膜形成組成物とした。
実施例1乃至実施例4、比較例1及び比較例2で調製されたレジスト下層膜形成組成物を、それぞれ、スピナーにより、半導体基板であるシリコンウェハー上に塗布した。そのシリコンウェハーをホットプレート上に配置し、205℃で1分間ベークし、レジスト下層膜(膜厚0.05μm)を形成した。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、それら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3で調製され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、シリコンウェハー上に塗布した。そのシリコンウェハーをホットプレート上に配置し、205℃で1分間ベークし、レジスト下層膜(膜厚0.10μm)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を用いてドライエッチング速度を測定した。
実施例1乃至実施例4、比較例1及び比較例2で調製され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、シリコンウェハー上に塗布した。そのシリコンウェハーをホットプレート上に配置し、205℃で1分間ベークし、レジスト下層膜(膜厚0.005μm)を形成した。そして、株式会社日立ハイテクノロジーズ製、高分解能電界放出形走査電子顕微鏡(FE-SEM)S-4800を用いて、白色点として観察されるレジスト下層膜上の欠陥数の比較を行った。結果を表2に示す。表2において、レジスト下層膜上の欠陥数は、倍率15000倍における16.7μm×12.6μmの範囲の欠陥数を数えることにより測定した。図1乃至図6は、上記FE-SEMにて、各実施例及び各比較例で調製された組成物を用いて形成したレジスト下層膜を上面から観察した際の、SEM像を示している。
Claims (9)
- 前記炭化水素基はtert-ブチル基又はiso-プロピル基である、請求項1に記載のリソグラフィー用レジスト下層膜形成組成物。
- 更に酸発生剤を含む、請求項1乃至請求項6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。
- 前記ポリマーの重量平均分子量は1000乃至100000である、請求項1乃至請求項7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。
- 請求項1乃至請求項8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厚さ1nm乃至20nmの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KrFエキシマレーザー、ArFエキシマレーザー、極端紫外線及び電子線からなる群から選択される放射線により露光する工程、並びに露光後にアルカリ性現像液によって現像する工程を含む、レジストパターンの形成方法。
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Cited By (5)
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WO2013141015A1 (ja) * | 2012-03-23 | 2013-09-26 | 日産化学工業株式会社 | Euvリソグラフィー用レジスト下層膜形成組成物 |
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JP5888523B2 (ja) | 2016-03-22 |
CN103415809A (zh) | 2013-11-27 |
TW201303510A (zh) | 2013-01-16 |
US8962234B2 (en) | 2015-02-24 |
CN103415809B (zh) | 2017-03-15 |
KR101804392B1 (ko) | 2017-12-04 |
JPWO2012124597A1 (ja) | 2014-07-24 |
TWI531864B (zh) | 2016-05-01 |
KR20140012111A (ko) | 2014-01-29 |
US20140004465A1 (en) | 2014-01-02 |
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