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WO2014171326A1 - Composition permettant de former un film de sous-couche de résine - Google Patents

Composition permettant de former un film de sous-couche de résine Download PDF

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Publication number
WO2014171326A1
WO2014171326A1 PCT/JP2014/059633 JP2014059633W WO2014171326A1 WO 2014171326 A1 WO2014171326 A1 WO 2014171326A1 JP 2014059633 W JP2014059633 W JP 2014059633W WO 2014171326 A1 WO2014171326 A1 WO 2014171326A1
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Prior art keywords
group
resist underlayer
underlayer film
film forming
forming composition
Prior art date
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PCT/JP2014/059633
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English (en)
Japanese (ja)
Inventor
橋本　圭祐
裕和 西巻
徹也 新城
安信 染谷
涼 柄澤
坂本　力丸
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Nissan Chemical Corp
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Nissan Chemical Corp
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Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to CN201480021117.6A priority Critical patent/CN105143979B/zh
Priority to JP2015512438A priority patent/JP6327481B2/ja
Priority to KR1020157027401A priority patent/KR102004697B1/ko
Publication of WO2014171326A1 publication Critical patent/WO2014171326A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/026—Wholly aromatic polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/02—Polyamines
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/142—Side-chains containing oxygen
    • C08G2261/1422—Side-chains containing oxygen containing OH groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3424—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms non-conjugated, e.g. paracyclophanes or xylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring

Definitions

  • the present invention relates to a resist underlayer film forming composition for a lithography process.
  • the present invention relates to a composition for forming a resist underlayer film that has high hardness and is less likely to cause wiggling of a resist pattern formed by a lithography process.
  • fine processing is performed by a lithography process.
  • the lithography process when the resist layer on the substrate is exposed with an ultraviolet laser such as a KrF excimer laser or an ArF excimer laser, the desired effect is caused by the standing wave generated by the reflection of the ultraviolet laser on the substrate surface.
  • an ultraviolet laser such as a KrF excimer laser or an ArF excimer laser
  • the desired effect is caused by the standing wave generated by the reflection of the ultraviolet laser on the substrate surface.
  • a resist pattern having a shape is not formed.
  • it is adopted to provide a resist underlayer film (antireflection film) between the substrate and the resist layer.
  • a novolak resin as a composition for forming a resist underlayer film.
  • Patent Document 1 and Patent Document 2 disclose a photoresist underlayer film forming material containing a resin having a repeating unit obtained by novolakizing a compound having a bisphenol group.
  • Patent Document 3 discloses a spin-coatable antireflection film composition containing a polymer having an aromatic ring condensed in three or more in the main chain of the polymer.
  • a lithography process is also known in which at least two resist underlayer films are formed and used as a mask material in order to reduce the thickness of the resist layer required in accordance with the miniaturization of the resist pattern.
  • the material forming the at least two layers include organic resins (for example, acrylic resins and novolac resins), silicon resins (for example, organopolysiloxane), and inorganic silicon compounds (for example, SiON, SiO 2 ).
  • organic resins for example, acrylic resins and novolac resins
  • silicon resins for example, organopolysiloxane
  • inorganic silicon compounds for example, SiON, SiO 2
  • an etching gas for example, fluorocarbon
  • Patent Document 4 discloses a composition containing a polymer containing a heterocyclic aromatic moiety.
  • the present invention solves the above problems. That is, the present invention provides the following formula (1): (Wherein X 1 represents a divalent organic group having 6 to 20 carbon atoms having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group or a hydroxy group, and X 2 Represents an organic group having 6 to 20 carbon atoms having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group or a hydroxy group, or a methoxy group. It is a resist underlayer film forming composition containing the polymer which has a structural unit represented, and a solvent.
  • Examples of the halogeno group described above and below will include a chloro group and a bromo group.
  • Examples of the divalent organic group having 6 to 20 carbon atoms having at least one aromatic ring described above and below will be, for example, a phenylene group, biphenylylene group, terphenylylene group, fluorenylene group, naphthylene group, anthrylene group, pyrenylene group (the following formula ( a-1) and a group represented by the following formula (a-2)), a carbazolylene group (a group represented by the following formula (b)) and a group represented by the following formula (c) (wherein n represents Represents 0 or 1.).
  • Examples of the organic group having 6 to 20 carbon atoms having at least one aromatic ring include a phenyl group, biphenylyl group, terphenylyl group, fluorenyl group, naphthyl group, anthryl group, pyrenyl group, carbazolyl group, and the following formula (d-1 And a group represented by the following formula (d-2) (wherein n represents 0 or 1).
  • the polymer is further represented by the following formula (2): (Wherein X 1 represents a C 6-20 divalent organic group having at least one aromatic ring optionally substituted with a halogeno group, a nitro group, an amino group, or a hydroxy group, and R 3 represents A phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a thienyl group or a pyridyl group; R 4 represents a hydrogen atom, a phenyl group or a naphthyl group; and R 3 and R 4 each represent a phenyl group, R 3 and R 4 may form a fluorene ring together with the same carbon atom to which they are attached. You may have a structural unit represented by these.
  • the resist underlayer film forming composition of the present invention may further contain at least one of a crosslinking agent, an acidic compound, a thermal acid generator and a surfactant as an optional component.
  • the resist underlayer film formed by using the resist underlayer film forming composition of the present invention has high hardness, and by applying the resist underlayer film, the bending of the pattern formed in the lithography process is suppressed. can do.
  • Examples of the structural unit of the polymer having the structural unit represented by the above formula (1) contained in the resist underlayer film forming composition of the present invention are represented by the following formulas (1-1) to (1-10). Structural units.
  • examples of the structural unit represented by the above formula (2) include a structural unit represented by the following formula (2-1).
  • the weight average molecular weight of the polymer contained in the resist underlayer film forming composition of the present invention is, for example, 2,000 to 10,000 in terms of standard polystyrene.
  • the polymer polymerizes a biphenol compound having two hydroxyphenyl groups, an aromatic compound or a heterocyclic compound, and if necessary, an aromatic aldehyde or an aromatic ketone in the presence of an acid catalyst such as a sulfonic acid compound. It can be synthesized by reaction.
  • the biphenol compound having two hydroxyphenyl groups used for the synthesis of the polymer include 3,3 ', 5,5'-tetramethoxymethyl-4,4'-dihydroxybiphenyl.
  • the aromatic compound used for the synthesis of the polymer include benzene, naphthalene, anthracene, pyrene, fluorene, and m-terphenyl.
  • heterocyclic compound used for the synthesis of the polymer examples include carbazole.
  • aromatic aldehyde used for the synthesis of the polymer examples include furfural, pyridinecarboxaldehyde, benzaldehyde, naphthylaldehyde, anthrylaldehyde, phenanthrylaldehyde, salicylaldehyde, phenylacetaldehyde, 3-phenylpropionaldehyde, tolylaldehyde, ( N, N-dimethylamino) benzaldehyde, acetoxybenzaldehyde, 1-pyrenecarboxaldehyde, anisaldehyde.
  • the aromatic ketone used in the synthesis of the polymer is a diaryl ketone, and examples thereof include diphenyl ketone, phenyl naphthyl ketone, dinaphthyl ketone, phenyl tolyl ketone, ditolyl ketone, and 9-fluorenone.
  • the biphenol compound used for the synthesis of the polymer is not limited to one type of compound, and two or more types may be used, and aromatic compounds, heterocyclic compounds, aromatic aldehydes and aromatic ketones are also limited to one type of compound. Two or more of them may be used.
  • the resist underlayer film forming composition of the present invention can further contain a crosslinking agent.
  • a cross-linkable compound having at least two cross-linking substituents is preferably used.
  • examples thereof include melamine compounds, substituted urea compounds and phenolic compounds having a crosslink forming substituent such as a methylol group or a methoxymethyl group.
  • Specific examples include compounds such as methoxymethylated glycoluril and methoxymethylated melamine, and examples include tetramethoxymethylglycoluril, tetrabutoxymethylglycoluril, and hexamethoxymethylmelamine.
  • examples of the substituted urea compound include tetramethoxymethylurea and tetrabutoxymethylurea.
  • examples of phenolic compounds include tetrahydroxymethyl biphenol, tetramethoxymethyl biphenol, and tetramethoxymethyl bisphenol.
  • cross-linking agent a compound having at least two epoxy groups can also be used.
  • Examples of such compounds include tris (2,3-epoxypropyl) isocyanurate, 1,4-butanediol diglycidyl ether, 1,2-epoxy-4- (epoxyethyl) cyclohexane, glycerol triglycidyl ether, diethylene glycol Diglycidyl ether, 2,6-diglycidylphenyl glycidyl ether, 1,1,3-tris [p- (2,3-epoxypropoxy) phenyl] propane, 1,2-cyclohexanedicarboxylic acid diglycidyl ester, 4,4 '-Methylenebis (N, N-diglycidylaniline), 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, trimethylolethane triglycidyl ether, bisphenol-A-diglycidyl ether, Epolide [registered trademark] GT-401
  • Examples of such an epoxy resin include YH-434 and YH-434L (manufactured by Nippon Kayaku Epoxy Manufacturing Co., Ltd.).
  • As the crosslinking agent a compound having at least two blocked isocyanate groups can also be used. Examples of such compounds include Takenate (registered trademark) B-830 and B-870N manufactured by Mitsui Chemicals, Inc. and VESTANAT (registered trademark) B1358 / 100 manufactured by Evonik Degussa.
  • As the cross-linking agent a compound having at least two vinyl ether groups can also be used.
  • Examples of such compounds include bis (4- (vinyloxymethyl) cyclohexylmethyl) glutarate, tri (ethylene glycol) divinyl ether, adipic acid divinyl ester, diethylene glycol divinyl ether, 1,2,4-tris (4-vinyl).
  • One kind selected from these various crosslinking agents may be added, or two or more kinds may be added in combination.
  • the content of the crosslinking agent is, for example, 2% by mass to 60% by mass with respect to the solid content excluding the solvent described later from the resist underlayer film forming composition of the present invention.
  • the resist underlayer film forming composition of the present invention can further contain an acidic compound.
  • the acidic compound serves as a catalyst for promoting the cross-linking reaction.
  • p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium-p-toluenesulfonate, salicylic acid, camphorsulfonic acid, 5-sulfosalicylic acid, 4-chlorobenzenesulfonic acid examples include 4-hydroxybenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalenesulfonic acid, citric acid, benzoic acid, sulfonic acid compounds such as hydroxybenzoic acid, and carboxylic acid compounds, and inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid.
  • a thermal acid generator can be contained.
  • the thermal acid generator also serves as a catalyst for promoting the crosslinking reaction, and examples thereof include quaternary ammonium salts of trifluoromethanesulfonic acid.
  • One kind selected from these acidic compounds and thermal acid generators may be added, or two or more kinds may be added in combination.
  • the content ratio of the acidic compound or thermal acid generator is, for example, 0.1% by mass to 20% by mass with respect to the solid content excluding the solvent described later from the resist underlayer film forming composition of the present invention.
  • the resist underlayer film forming composition of the present invention can further contain a surfactant.
  • the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene Polyoxyethylene alkyl aryl ethers such as ethylene nonylphenyl ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan Sorbitan fatty acid esters such as tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as rubitan monopalmitate, polyoxyethylene sorbitan monostea
  • One kind selected from these surfactants may be added, or two or more kinds may be added in combination.
  • the content rate of the said surfactant is 0.01 mass% thru
  • the resist underlayer film forming composition of the present invention can be prepared by dissolving each of the above components in an appropriate solvent, and is used in a uniform solution state.
  • solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether acetate, propylene glycol.
  • the step of applying and baking the resist underlayer film forming composition of the present invention includes a base material (for example, a silicon wafer, which is a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a metal film such as aluminum or tungsten).
  • the composition may be coated by a suitable coating method such as a spinner or a coater, and then baked using a heating means such as a hot plate. Baking conditions are appropriately selected from a baking temperature of 100 ° C. to 400 ° C. and a baking time of 0.3 minutes to 10 minutes.
  • An organopolysiloxane film is formed as a second resist underlayer film on the first resist underlayer film formed by the above process, and a resist pattern is formed thereon.
  • the second resist underlayer film may be a SiON film or a SiN film formed by a vapor deposition method such as CVD or PVD.
  • an antireflection film (BARC) may be formed as a third resist underlayer film on the second resist underlayer film, and the third resist underlayer film is a resist shape correction film having no antireflection ability. May be.
  • exposure is performed through a mask (reticle) for forming a predetermined pattern or by direct drawing.
  • the exposure source for example, g-line, i-line, KrF excimer laser, ArF excimer laser, EUV, or electron beam can be used.
  • post-exposure heating Post Exposure Bake
  • development is performed with a developer (for example, an aqueous 2.38 mass% tetramethylammonium hydroxide solution), and further rinsed with a rinse solution or pure water to remove the used developer.
  • the resist pattern is dried and post-baked in order to improve adhesion to the base.
  • the etching process performed after forming the resist pattern is performed by dry etching.
  • the etching gas used for dry etching include CHF 3 , CF 4 , and C 2 F 6 for the second resist underlayer film (organopolysiloxane film).
  • the resist underlayer film forming composition of the present invention For the formed first resist underlayer film, for example, O 2 , N 2 O, NO 2 can be mentioned, and for the surface having a step or a concave portion and / or a convex portion, for example, CHF 3 , CF 4 , C 2 F 6 is mentioned. Further, argon, nitrogen or carbon dioxide can be mixed with these gases.
  • TMOM-Py a target polymer having a structural unit represented by the following formula (3) (hereinafter referred to as TMOM-Py in this specification) (Abbreviated) 28.6 g was obtained.
  • the weight average molecular weight of the obtained TMOM-Py measured in terms of polystyrene by GPC was 2600.
  • TMOM target polymer having two structural units represented by the following formula (4)
  • -Cz-PCA target polymer having two structural units represented by the following formula (4)
  • the obtained TMOM-Cz-PCA had a weight average molecular weight of 8,900 measured by polystyrene conversion by GPC.
  • TMOM-Na a target polymer having a structural unit represented by the following formula (5) (hereinafter referred to as TMOM-Na in this specification). (Abbreviated) 5.9 g was obtained.
  • the obtained TMOM-Na had a weight average molecular weight of 5,000 as measured by GPC in terms of polystyrene.
  • the mixture was allowed to cool to 60 ° C., diluted with chloroform (34 g, manufactured by Kanto Chemical Co., Inc.), and reprecipitated into methanol (168 g, manufactured by Kanto Chemical Co., Inc.).
  • the obtained precipitate was filtered and dried in a vacuum dryer at 80 ° C. for 24 hours to obtain 9.37 g of a target polymer having a structural unit represented by the following formula (6).
  • the weight average molecular weight of the obtained polymer measured by polystyrene conversion by GPC was 2,800.
  • Example 1 To 20 g of the polymer obtained in Synthesis Example 1, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a resist underlayer film forming composition used in a lithography process using a multilayer film. did.
  • Megafac R-30 manufactured by DIC Corporation
  • Example 2 To 20 g of the polymer obtained in Synthesis Example 2, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a resist underlayer film forming composition used in a lithography process using a multilayer film. did.
  • Megafac R-30 manufactured by DIC Corporation
  • Example 3 To 20 g of the polymer obtained in Synthesis Example 3, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a resist underlayer film forming composition used in a lithography process using a multilayer film. did.
  • Megafac R-30 manufactured by DIC Corporation
  • Comparative Example 1 To 20 g of the polymer obtained in Comparative Synthesis Example 1, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Thereafter, the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a resist underlayer film forming composition used in a lithography process using a multilayer film. did.
  • Megafac R-30 manufactured by DIC Corporation
  • Comparative Example 2 To 20 g of the polymer obtained in Comparative Synthesis Example 1, 3.0 g of TMOM-BP (produced by Honshu Chemical Industry Co., Ltd.) as a crosslinking agent, 0.6 g of pyridinium paratoluenesulfonate as a catalyst, and Megafac R-30 (as a surfactant) DIC Co., Ltd.) (0.06 g) was mixed and dissolved in 80 g of cyclohexanone to obtain a solution.
  • TMOM-BP produced by Honshu Chemical Industry Co., Ltd.
  • Megafac R-30 as a surfactant
  • the mixture is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a resist underlayer film forming composition used in a lithography process using a multilayer film. did.
  • the resist underlayer films formed by baking at 400 ° C. for 2 minutes using the resist underlayer film forming compositions of Examples 1 to 3 according to the present invention are those of Comparative Example 1 and Comparative Example 2. It was found that the resist underlayer film was harder than the resist underlayer film formed by baking under the same conditions using the resist underlayer film forming composition.
  • the resist underlayer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 240 ° C. for 1 minute or 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 0.05 ⁇ m). These resist underlayer films were measured for refractive index (n value) and optical absorption coefficient (also referred to as k value or attenuation coefficient) at a wavelength of 193 nm using a spectroscopic ellipsometer. The results are shown in Table 2.
  • the resist underlayer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 0.2 ⁇ m). These resist underlayer films were scraped from the silicon wafer to obtain a powder. The thermogravimetric phenomenon at 400 ° C. of the obtained powder was measured with TG / DTA (TG-DTA2010SR manufactured by BRUKER). The results are shown in Table 3.
  • the etcher and etching gas used for the measurement of the dry etching rate are as follows.
  • the resist underlayer film forming compositions prepared in Examples 1 to 3 were each applied on a silicon wafer using a spin coater. The applied wafer was baked on a hot plate at 240 ° C. for 1 minute or 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 0.25 ⁇ m). Next, the dry etching rate of these resist underlayer films was measured using CF 4 gas as an etching gas.
  • phenol novolac resin commercial product, weight average molecular weight Mw measured in terms of polystyrene by GPC is 2000, polydispersity Mw / Mn is 2.5
  • the applied wafer was baked on a hot plate at 205 ° C. for 1 minute to form a phenol novolac resin film (film thickness: 0.25 ⁇ m).
  • CF 4 gas was used as an etching gas, and the dry etching rate of the phenol novolac resin film was measured.
  • the resist underlayer film forming compositions prepared in Examples 1 to 3 and Comparative Example 2 were each applied onto a silicon wafer with a silicon oxide film using a spin coater. The applied wafer was baked on a hot plate at 400 ° C. for 2 minutes to form a resist underlayer film (film thickness 200 nm).
  • a known silicon hard mask forming composition containing polysiloxane was applied onto the resist underlayer film and baked at 240 ° C. for 1 minute to form a silicon hard mask layer (film thickness: 45 nm). Further, a resist solution (PAR855 S90 (manufactured by Sumitomo Chemical Co., Ltd.)) was applied thereon and baked at 100 ° C.
  • the above-described pattern formation is performed using the resist underlayer film forming composition prepared in Examples 1 to 3.
  • the process was performed, and the pattern width at which the resulting pattern began to wiggle was observed with an electron microscope. Since the processing of the substrate based on the faithful pattern becomes impossible due to the occurrence of pattern bending, it is necessary to process the substrate with the pattern width (limit pattern width) immediately before the occurrence of the pattern bending. The narrower the limit pattern width at which pattern bending starts to occur, the finer the substrate can be processed.
  • a length measurement scanning electron microscope manufactured by Hitachi High-Technologies Corporation was used for resolution measurement. Table 5 shows the measurement results.
  • the resist underlayer film forming composition used in the lithography process using the multilayer film of the present invention can provide a resist underlayer film that can also have an effect as an antireflection film. Moreover, it turned out that the resist underlayer film forming composition of this invention has the heat resistance which can form a hard mask in the upper layer by CVD method. Further, even when the pattern width is narrowed, a good pattern is obtained in which pattern bending is difficult to occur, and a good pattern with no bend is obtained at a pattern width of at least about 50 nm.

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  • Structural Engineering (AREA)
  • Physics & Mathematics (AREA)
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Abstract

[Problème] L'invention concerne une nouvelle composition de formation d'un film de sous-couche de résine. [Solution] L'invention concerne une composition permettant de former un film de sous-couche de résine, ladite composition contenant un solvant et un polymère qui a une unité constitutionnelle qui peut être représentée par la formule (1). (1) (Dans la formule (1), X1 représente un groupe organique divalent C6 - 20 qui a au moins un anneau aromatique qui peut être remplacé par un groupe halogène, un groupe nitro, un groupe amino, ou un groupe hydroxy ; et X2 représente un groupe methoxy ou un groupe organique C6 - 20 qui a au moins un anneau aromatique qui peut être remplacé par un groupe halogène, un groupe nitro, un groupe amino, ou un groupe hydroxy).
PCT/JP2014/059633 2013-04-17 2014-04-01 Composition permettant de former un film de sous-couche de résine Ceased WO2014171326A1 (fr)

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CN201480021117.6A CN105143979B (zh) 2013-04-17 2014-04-01 抗蚀剂下层膜形成用组合物
JP2015512438A JP6327481B2 (ja) 2013-04-17 2014-04-01 レジスト下層膜形成組成物
KR1020157027401A KR102004697B1 (ko) 2013-04-17 2014-04-01 레지스트 하층막 형성 조성물

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CN107531597A (zh) * 2015-03-06 2018-01-02 三菱瓦斯化学株式会社 化合物、树脂、光刻用下层膜形成材料、光刻用下层膜、图案形成方法以及化合物或树脂的纯化方法
WO2018198960A1 (fr) * 2017-04-25 2018-11-01 日産化学株式会社 Composition de formation de film de sous-couche de réserve utilisant un composé de fluorène
US20190354018A1 (en) * 2017-01-13 2019-11-21 Nissan Chemical Corporation Resist underlayer film-forming composition containing amide solvent
WO2021112194A1 (fr) * 2019-12-04 2021-06-10 三菱瓦斯化学株式会社 Composition permettant de former un film de sous-couche pour lithographie, film de sous-couche pour lithographie, procédé de formation de motif de réserve, procédé de formation de motif de circuit, oligomère et procédé de purification
US20220089811A1 (en) * 2019-01-11 2022-03-24 Mitsubishi Gas Chemical Company, Inc. Composition for film formation, resist composition, radiation-sensitive composition, method for producing amorphous film, resist pattern formation method, composition for underlayer film formation for lithography, method for producing underlayer film for lithography, and circuit pattern formation method
WO2022107759A1 (fr) * 2020-11-19 2022-05-27 日産化学株式会社 Composition filmogène de sous-couche de réserve
KR20220149704A (ko) 2020-02-28 2022-11-08 닛산 가가쿠 가부시키가이샤 레지스트 하층막 형성 조성물
KR20220149703A (ko) 2020-02-28 2022-11-08 닛산 가가쿠 가부시키가이샤 폴리머의 제조방법
JP2023080138A (ja) * 2018-05-01 2023-06-08 東京応化工業株式会社 ハードマスク形成用組成物及び電子部品の製造方法
KR20240009452A (ko) 2021-05-18 2024-01-22 닛산 가가쿠 가부시키가이샤 레지스트 하층막 형성 조성물
KR20250084142A (ko) 2022-10-06 2025-06-10 닛산 가가쿠 가부시키가이샤 레지스트 하층막 형성 조성물

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KR102383692B1 (ko) * 2017-06-30 2022-04-05 동우 화인켐 주식회사 하드마스크용 조성물
KR102822613B1 (ko) * 2020-03-30 2025-06-19 닛산 가가쿠 가부시키가이샤 레지스트 하층막 형성 조성물
US20230203299A1 (en) * 2020-06-19 2023-06-29 Nissan Chemical Corporation Resist underlayer film- forming composition using diarylmethane derivative

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EP3266759A4 (fr) * 2015-03-06 2018-10-17 Mitsubishi Gas Chemical Company, Inc. Composé, résine, matériau pour former un film de sous-couche pour lithographie, film de sous-couche pour lithographie, procédé de formation de motif et procédé de purification d'un composé ou d'une résine
CN107531597A (zh) * 2015-03-06 2018-01-02 三菱瓦斯化学株式会社 化合物、树脂、光刻用下层膜形成材料、光刻用下层膜、图案形成方法以及化合物或树脂的纯化方法
US20190354018A1 (en) * 2017-01-13 2019-11-21 Nissan Chemical Corporation Resist underlayer film-forming composition containing amide solvent
US20240006183A1 (en) * 2017-01-13 2024-01-04 Nissan Chemical Corporation Resist underlayer film-forming composition containing amide solvent
US11798810B2 (en) * 2017-01-13 2023-10-24 Nissan Chemical Corporation Resist underlayer film-forming composition containing amide solvent
WO2018198960A1 (fr) * 2017-04-25 2018-11-01 日産化学株式会社 Composition de formation de film de sous-couche de réserve utilisant un composé de fluorène
JPWO2018198960A1 (ja) * 2017-04-25 2020-03-12 日産化学株式会社 フルオレン化合物を用いたレジスト下層膜形成組成物
JP7056651B2 (ja) 2017-04-25 2022-04-19 日産化学株式会社 フルオレン化合物を用いたレジスト下層膜形成組成物
JP2023080138A (ja) * 2018-05-01 2023-06-08 東京応化工業株式会社 ハードマスク形成用組成物及び電子部品の製造方法
JP7507919B2 (ja) 2018-05-01 2024-06-28 東京応化工業株式会社 ハードマスク形成用組成物及び電子部品の製造方法
US20220089811A1 (en) * 2019-01-11 2022-03-24 Mitsubishi Gas Chemical Company, Inc. Composition for film formation, resist composition, radiation-sensitive composition, method for producing amorphous film, resist pattern formation method, composition for underlayer film formation for lithography, method for producing underlayer film for lithography, and circuit pattern formation method
WO2021112194A1 (fr) * 2019-12-04 2021-06-10 三菱瓦斯化学株式会社 Composition permettant de former un film de sous-couche pour lithographie, film de sous-couche pour lithographie, procédé de formation de motif de réserve, procédé de formation de motif de circuit, oligomère et procédé de purification
JPWO2021112194A1 (fr) * 2019-12-04 2021-06-10
KR20220149703A (ko) 2020-02-28 2022-11-08 닛산 가가쿠 가부시키가이샤 폴리머의 제조방법
KR20220149704A (ko) 2020-02-28 2022-11-08 닛산 가가쿠 가부시키가이샤 레지스트 하층막 형성 조성물
KR20230108255A (ko) 2020-11-19 2023-07-18 닛산 가가쿠 가부시키가이샤 레지스트 하층막형성 조성물
JPWO2022107759A1 (fr) * 2020-11-19 2022-05-27
WO2022107759A1 (fr) * 2020-11-19 2022-05-27 日産化学株式会社 Composition filmogène de sous-couche de réserve
KR20240009452A (ko) 2021-05-18 2024-01-22 닛산 가가쿠 가부시키가이샤 레지스트 하층막 형성 조성물
KR20250084142A (ko) 2022-10-06 2025-06-10 닛산 가가쿠 가부시키가이샤 레지스트 하층막 형성 조성물

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CN105143979A (zh) 2015-12-09
CN105143979B (zh) 2019-07-05
KR20160002741A (ko) 2016-01-08
KR102004697B1 (ko) 2019-07-29
JPWO2014171326A1 (ja) 2017-02-23
JP6327481B2 (ja) 2018-05-23

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