WO2006077748A1 - 保護されたカルボキシル基を有する化合物を含むリソグラフィー用下層膜形成組成物 - Google Patents
保護されたカルボキシル基を有する化合物を含むリソグラフィー用下層膜形成組成物 Download PDFInfo
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- WO2006077748A1 WO2006077748A1 PCT/JP2006/300080 JP2006300080W WO2006077748A1 WO 2006077748 A1 WO2006077748 A1 WO 2006077748A1 JP 2006300080 W JP2006300080 W JP 2006300080W WO 2006077748 A1 WO2006077748 A1 WO 2006077748A1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
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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
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/094—Multilayer resist systems, e.g. planarising layers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
Definitions
- Lithographic underlayer film forming composition comprising a compound having a protected carboxyl group
- the present invention relates to a novel composition for forming an underlayer film for lithography, an underlayer film formed from the composition, and a method for forming a photoresist pattern using the underlayer film.
- the present invention provides a lower layer antireflection film that reduces reflection of exposure light from a substrate applied to a photoresist layer applied on a semiconductor substrate in a lithography process for manufacturing a semiconductor device, and planarizes an uneven semiconductor substrate.
- the present invention relates to a composition and a method for forming the underlayer film.
- the present invention also relates to a background art for forming an underlayer film for lithography that can be used to fill holes formed in a semiconductor substrate.
- an organic antireflection film composed of a light-absorbing substance and a polymer compound is used because of its ease of use.
- an acrylic-resin-type antireflection film having a hydroxyl group and a light-absorbing group in the same molecule or a hydroxyl group and a light-absorbing group in the same molecule.
- a novolac greaves type antireflection film for example, a novolac greaves type antireflection film.
- the properties required for the organic antireflection film are that it has a large absorbance to light and radiation, does not cause intermixing with the photoresist layer (is insoluble in the photoresist solvent), and is heated and baked. In some cases, diffusion of low molecular weight materials from the antireflection film to the upper photoresist does not occur, and the dry etching rate is higher than that of the photoresist.
- Patent Document 1 Patent Document 2, Patent Document 3, Patent Document 4.
- Patent Document 2 JP 2002-47430 A
- Patent Document 3 Japanese Patent Laid-Open No. 2002-190519
- Patent Document 4 International Publication No. 02Z05035 Pamphlet
- Patent Document 5 Japanese Patent Laid-Open No. 2002-128847
- Patent Document 6 International Publication No. 04Z090640 Pamphlet
- An object of the present invention is to provide a composition for forming an underlayer film for lithography that can be used in the manufacture of a semiconductor device. Then, the lower layer film for forming the lower layer film for forming the lower layer film and the lower layer film for lithography, which does not cause intermixing with the photoresist layer applied and formed on the upper layer and has a higher dry etching speed than the photoresist layer, is formed. It is to provide a composition.
- an object of the present invention is to provide a lower layer antireflection film for reducing the reflection of exposure light from a substrate on a photoresist layer formed on a semiconductor substrate in a lithography process for manufacturing a semiconductor device.
- a flat film for flattening a semiconductor substrate, and a lower layer film for lithography and a lower layer film that can be used as a film for preventing contamination of a photoresist layer by a substance that generates a semiconductor substrate force during heating and baking are formed. It is providing the lower layer film forming composition for.
- Another object of the present invention is to provide a method for forming an underlayer film for lithography using the underlayer film forming composition and a method for forming a photoresist pattern.
- Another object of the present invention is to provide a method for flattening the surface of a semiconductor substrate having holes having an aspect ratio of 1 or more represented by a height Z diameter.
- R, R and R are each a hydrogen atom or a carbon atom having 1 to: LO alkyl
- R represents an alkyl group having 1 to: LO carbon atoms, and R and R are bonded to each other.
- a composition for forming an underlayer film for lithography comprising a compound having two or more protected carboxyl groups represented by formula (II), a compound having two or more epoxy groups, and a solvent;
- the compound having two or more protected carboxyl groups represented by the formula (1) is a polymer having two or more protected carboxyl groups represented by the formula (1).
- the compound having two or more protected carboxyl groups represented by the formula (1) has a molecular weight having 2 to 6 protected carboxyl groups represented by the formula (1).
- the composition for forming a lower layer film for lithography according to the first aspect which is a compound having 1500 or less compounds
- the compound having two or more epoxy groups is a polymer having two or more epoxy groups.
- the composition for forming an underlayer film for lithography as described in the viewpoint, as a fifth aspect, the compound having two or more epoxy groups is a compound having a molecular weight of 1500 or less having two to six epoxy groups.
- Lower layer film forming composition for lithography is a compound having 1500 or less having two to six epoxy groups.
- a composition for forming a lower layer film for lithography according to the second aspect which is a polymer having a unit structure represented by:
- the polymer having two or more epoxy groups is represented by the formula (3):
- the underlayer film-forming composition for lithography according to the fourth aspect which is a polymer having a unit structure represented by
- a compound power having 2 to 6 protected carboxyl groups represented by the formula (1) and having a molecular weight of 1500 or less represented by the formula (1) and having a molecular weight of 1500 or less Formula (4):
- X represents a hydrogen atom, an alkyl group having 1 to carbon atoms: an alkyl group having 1 to LO, an alkyl group having 1 to carbon atoms: an alkoxy group, a nitro group, a cyano group or a halogen group having LO;
- m is 2 Is an integer of ⁇ 6
- a composition for forming an underlayer film for lithography according to the third aspect which is a compound represented by:
- a compound having 2 to 6 protected carboxyl groups represented by the formula (1) and having a molecular weight of 1500 or less has 2 to 3 protected carboxyl groups represented by the formula (1).
- an underlayer film for use in the manufacture of a semiconductor device comprising applying and baking the underlayer film forming composition for lithography according to any one of the first to ninth aspects on a semiconductor substrate.
- An eleventh aspect is a method of flattening a surface of a semiconductor substrate having holes having an aspect ratio ⁇ or more indicated by a height Z diameter, wherein any one of the first to ninth aspects is formed on the semiconductor substrate.
- a method for forming a photoresist pattern used for manufacturing a semiconductor device, comprising: a step of forming a resist layer; a step of exposing the semiconductor substrate covered with the lower layer film and the photoresist layer; and a step of developing after exposure. is there.
- composition for forming an underlayer film for lithography of the present invention can provide an excellent underlayer film that has a higher dry etching rate than that of a photoresist and that does not cause intermixing with the photoresist.
- the composition of the lower layer film for lithography of the present invention makes it possible to flatten the surface of a semiconductor substrate having holes whose aspect ratio represented by height Z diameter is 1 or more.
- a high filling property inside a hole can be achieved without generating voids (gap).
- the film thickness of a photoresist or the like applied and formed thereon can be increased. Uniformity can be increased. Therefore, a good photoresist pattern shape can be formed even in a process using a substrate having holes.
- composition for forming a lower layer film for lithography having excellent storage stability can be provided.
- an underlayer film that can be used as an antireflection film, a flat film, a protective film for preventing contamination of a photoresist layer called resist boiling, and the like. can be formed. This makes it possible to easily and accurately form a photoresist pattern in a lithography process for manufacturing a semiconductor device.
- FIG. 1 is a cross-sectional view of a state in which a lower layer film is formed on a substrate having holes.
- a is the depth of the recess in the lower layer film at the center of the hole, and b is used.
- the initial hole depth in the substrate, c is the underlying film, and d is the substrate.
- the composition for forming an underlayer film for lithography of the present invention comprises a compound represented by the formula (1) having two or more protected carboxyl groups, a compound having two or more epoxy groups, and a solvent.
- the underlayer film forming composition of this invention can contain a light absorbing compound, surfactant, a photo-acid generator etc. as an arbitrary component.
- the ratio of the solid content in the composition for forming a lower layer film for lithography of the present invention is not particularly limited as long as each component is uniformly dissolved, but is, for example, 0.1 to 70% by mass, or 1 to 50 % By mass, or 5-40% by mass, or 10-30% by mass.
- the solid content is a value obtained by removing all components, solvent components, and the lower layer film forming composition for lithography.
- the ratio of the compound having two or more protected carboxyl groups represented by the formula (1) and the compound having two or more epoxy groups in the solid content is 70% by mass or more. : LOO% by mass, 80-99% by mass, or 90-99% by mass.
- R, R and R are each a hydrogen atom or a carbon atom having 1 to
- R represents an alkyl group having 1 to 10 carbon atoms.
- R and R are bonded together May form a ring, that is, R and R are bonded to each other, and the two between R and R
- a ring structure may be formed together with the carbon atom and one oxygen atom.
- the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a normal butyl group, a normal octyl group, an isopropyl group, a tert-butyl group, a 2-ethyl hexyl group, and a cyclohexyl group.
- R and R may be bonded to each other to form a ring.
- Examples of the ring formed include a tetrahydrofuran ring and a tetrahydropyran ring.
- the compound having a protected carboxyl group represented by the formula (1) can be produced by reacting the compound having a carboxyl group with the vinyl ether compound represented by the formula (5).
- the reaction between a compound having a carboxyl group and a butyl ether compound is, for example, as described in Journal of the Adhesion Society of Japan, Vol. 34 (Vol. 34), pages 352 to 356, using phosphoric acid as a catalyst at room temperature. Can be carried out by stirring.
- a compound having a carboxyl group and a compound of formula (5) a polymer having two or more protected carboxyl groups represented by formula (1) and a protected compound represented by formula (1) are used.
- a compound having 2 to 6 carboxyl groups and a molecular weight of about 2000 or less can be produced.
- Examples of the butyl ether compound represented by the formula (5) include methyl vinyl ether, ethinolevino reetenole, isopropino levino minoatenore, nonolemanole bubutino levino reete nore, and 2-ethenorehexino levino oleore.
- Aliphatic ether compounds such as etherol, tert-butynolevininoreetherenole, cyclohexyl vinyl ether, 2,3-dihydrofuran, 4-methyl-2,3-dihydrofuran, 2,3-dihydro Examples thereof include cyclic blue ether compounds such as 4H-pyran.
- the product is not particularly limited as long as it is a compound having two or more carboxyl groups.
- Examples include low molecular weight compounds having strong lpoxyl groups (V, compounds not having a molecular weight of about 2000 or less), polymers having carboxyl groups, and the like.
- Examples of low molecular weight compounds having two or more carboxyl groups include phthalic acid, isophthalic acid, terephthalic acid, 1, 2, 4, 5 benzenetetracarboxylic acid (pyromellitic acid), 1, 3, 5 benzene Tricarboxylic acid (trimesic acid), 1, 2, 4 benzenetricarboxylic acid (trimellitic acid), adipic acid, maleic acid, butanetetracarboxylic acid, tris (2-carboxyethyl) isocyanuric acid, naphthalene-2-carboxylic acid, naphthalene 1, 2, dicarboxylic acid, pamoic acid, 1, 1, 1-binaphthalene 1, 2, 2, 1-dicarboxylic acid, anthracene 9, 10 dicarboxylic acid, itaconic acid, glutaric acid, 1,2 cyclohexanedicarboxylic acid Acid, 1, 2, 3, 4-cyclopentanetetracarboxylic acid, bifer
- the molecular weight of the compound having two or more protected carboxyl groups represented by the formula (1) produced from these compounds is preferably 200 or more. If the molecular weight force is smaller than this, there may be a problem of sublimation during firing for forming the lower layer film.
- the molecular weight is, for example, 200 to 2000, or 250 to 1500, or 300 to 1000, or 400 to 800.
- the protection represented by the formula (1) which is a reaction site at the time of forming the underlayer film is considered from the viewpoint. It is necessary to have two or more rupoxyl groups. It is preferable to use a compound having 2 to 6 or 3 to 4 protected carboxyl groups represented by the formula (1).
- a compound represented by the formula (4) can also be used.
- X is a hydrogen atom, carbon It represents an alkyl group having 1 to 10 atoms, an alkoxy group having 1 to 10 carbon atoms, a nitro group, a cyan group or a halogen group.
- X may be the same or different.
- the molecular weight of the compound of formula (4) is 200 to 20000, or 1500 or less, such as 250 to 1500, or 300 to 1000, or 400 to 800.
- Examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a normal butyl group, a normal octyl group, an isopropyl group, a tert butyl group, a 2-ethyl hexyl group and a cyclohexyl group.
- Examples of the alkoxy group having 1 to 10 carbon atoms include a methoxy group, an ethoxy group, a normal butoxy group, a normal octyloxy group, an isopropoxy group, a tert butoxy group, a 2-ethylhexyloxy group, and a cyclohexyloxy group. Can be mentioned.
- the halogen group includes a fluoro group, a black mouth group, a bromo group, and an iodine group.
- the compound represented by the formula (4) can be produced by reacting the corresponding carboxylic acid compound with the compound of the formula (5).
- Examples of the carboxylic acid compound used in the production of the compound of formula (4) include phthalic acid, isophthalic acid, terephthalic acid, 1, 2, 4, 5 benzenetetracarboxylic acid, 1, 3, 5 Zentricarboxylic acid, 1, 2, 4 benzenetricarboxylic acid, 1, 2, 3 benzenetricarboxylic acid (hemimellitic acid), 1, 2, 3, 4 benzenetetracarboxylic acid (merophanoic acid), 1, 2, 3 , 5-benzenetetracarboxylic acid (pre-acid) and benzenehexacarboxylic acid (mellitic acid).
- Examples of the compound having two or more protected carboxyl groups represented by the formula (1) include isocyanuric acid compounds having two to three protected carboxyl groups represented by the formula (1). Can be used. Such isocyanuric acid compounds include tris (2-carboxetyl) isocyanuric acid, bis (2-carboxyethyl) isocyanuric acid, tris (2-forcecarboxyl) isocyanuric acid, bis (2-carboxypropyl) isocyanuric acid.
- Examples of the compound having a carboxyl group to be reacted with the vinyl ether compound represented by the formula (5) include a polymer having two or more carboxyl groups.
- a polymer is not particularly limited, and examples thereof include a polymer containing an addition polymerizable monomer having a carboxyl group such as acrylic acid, methacrylic acid, belbenzoic acid and maleic acid as a unit structure.
- Such polymers include homopolymers such as polyacrylic acid and polymethacrylic acid, copolymers of acrylic acid and methacrylic acid, copolymers of tallic acid and bull benzoic acid, copolymers of methacrylic acid and bull benzoic acid, and methacrylic acid. Mention may be made of copolymers such as maleic acid copolymers.
- Such a polymer examples include the above-mentioned addition polymerizable monomer having a carboxyl group and an acrylic ester compound, a methacrylic ester compound, an acrylamide compound, a methacrylamide compound, a vinyl compound, a styrene compound, Mention may be made of polymers produced by combining maleimide compounds, maleic anhydride, and other addition polymerizable monomers such as acrylonitrile.
- copolymers of acrylic acid and methacrylic ester compounds for example, copolymers of acrylic acid and methacrylic ester compounds, copolymers of acrylic acid and acrylamide compounds, copolymers of methacrylic acid and methacrylic ester compounds, copolymers of methacrylic acid and acrylate compounds, copolymers of acrylic acid and acrylate compounds Copolymers of methacrylic acid and styrene compounds, copolymers of acrylic acid and butyl compounds, copolymers of butyl benzoic acid and methacrylate compounds, copolymers of maleic acid and methacrylate compounds, and copolymers of maleic acid and maleimide compounds, etc.
- a polymer having two or more protected carboxyl groups represented by formula (1) can be produced by reacting the polymer having two or more carboxyl groups with the compound of formula (5). it can.
- Acrylic acid ester compounds include methyl acrylate, ethyl acrylate, isopyl pill acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, 2-hydroxy acrylate.
- methacrylic acid ester compound examples include ethyl methacrylate, normal propyl methacrylate, normal pentyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate.
- acrylamide compounds include acrylamide, N-methyl acrylamide, N-ethyl acrylamide, N-benzyl acrylamide, N-phenyl acrylamide, and N, N-dimethyl acrylamide.
- methacrylamide compound examples include methacrylamide, N-methylmethacrylamide, N-ethylmethacrylamide, N-benzylmethacrylamide, N-phenylmethacrylamide, and N, Ndimethylmethacrylamide.
- bur compound examples include butyl ether, methyl butyl ether, benzyl benzene ether, 2-hydroxyethyl vinyl ether, vinyl vinyl ether, and propyl butyl ether.
- styrene compound examples include styrene, methylstyrene, chlorostyrene, bromostyrene, and hydroxystyrene.
- maleimide compounds include maleimide, N-methylmaleimide, N-phenol maleimide, and N-cyclohexyl maleimide.
- the compound having two or more protected carboxyl groups represented by formula (1) in the composition for forming a lower layer film for lithography of the present invention may also be represented by formula (2), formula (6) or formula (7 A polymer having a unit structure represented by) can be used.
- R 1, R 2, R 3 and R 4 are as defined in formula (1), R 5 represents a hydrogen atom or a methyl group, and in formula (6) And R 6 represents an alkyl group having 1 to: LO carbon atoms.
- a polymer having a unit structure represented by formula (6) or formula (7) is a polymer having a unit structure having a carboxyl group corresponding to formula (2), formula (6) or formula (7), respectively. It can be produced by reaction with a vinyl ether compound represented by the formula (5). Manufactured by reacting a polymer containing an addition-polymerizable monomer of allylic acid, methacrylic acid, butylbenzoic acid or maleic acid monoester as a unit structure with a butyl ether compound represented by formula (5) Can do.
- the polymer having a unit structure represented by the formula (2), formula (6) or formula (7) is 0.01 or more, or 0.1 or more with respect to the total number of repeating unit structures constituting the polymer.
- addition polymerizable monomers include 1-methoxyethyl methacrylate, 1 ethoxyethyl methacrylate, 1 isopropoxycetyl methacrylate, 1-nonole manolate.
- Hexaloxetyl metatalylate and hemiacetal ester compounds of methacrylic acid such as tetrahydro-2H-pyran-2-ylmethalate, 1-methoxyethyl acrylate, 1 tert butoxychetyl acrylate, 1 isopropoxy Hemiacetal ester compounds such as ethyl acrylate, 1 normal butoxetyl acrylate, and tetrahydro 2H-pyran 2-yl phthalate, 1-etoxetyl 4-bi-benzoate, and methyl (1 ethoxyethyl)
- maleate maleate.
- the monomers of the formulas (8) to (10) can be produced by reacting acrylic acid, methacrylic acid, butyl benzoic acid or maleic acid monoester with a butyl ether compound represented by the formula (5). it can.
- addition polymerizable monomers may be used for the production of the polymer containing the unit structure represented by the formula (2), formula (6) or formula (7). It can be used together.
- addition-polymerizable monomers include acrylic acid ester compounds, methacrylic acid ester compounds, acrylamide compounds, methacrylamide compounds, beryl compounds, styrene compounds, maleimide compounds, and maleic anhydride. And talis-trills.
- the polymer using the above addition-polymerizable monomer is prepared by dissolving the addition-polymerizable monomer and an optionally added chain transfer agent (10% or less based on the mass of the monomer) in an organic solvent, and then polymerizing.
- the polymerization can be carried out by adding an initiator and then adding a polymerization terminator.
- the addition amount of the polymerization initiator is 1 to 10% with respect to the mass of the monomer, and the addition amount of the polymerization terminator is 0.01 to 0.2%.
- the organic solvent used include propylene glycol monomethyl ether, propylene glycol monopropyl ether, ethyl lactate, and dimethylformamide, etc.
- Chain transfer agents such as dodecanethiol and dodecylthiol, etc.
- Polymerization initiators such as azobis, isobutyoxy-tolyl, and azobiscyclohexane Hexanecarbo-tolyl isokinetic force
- 4-methoxyphenol and the like can be mentioned as a polymerization terminator.
- the reaction temperature is 30-100 ° C,
- the response time is appropriately selected from 1 to 24 hours.
- the monomers of formulas (8) to (10) and other addition polymerizable monomers are used.
- the use ratio is, for example, 100Z1 to LZ100 as an addition-polymerizable monomer Z having a protected carboxyl group represented by the formula (1) and other addition polymerizable monomers represented by the formula (1).
- the weight average molecular weight of the polymer is, for example, 1000 to 500000, for example 1000 to 200000, 3000 to 150,000, or 3000 to 50000.
- the compound having two or more protected carboxyl groups represented by the formula (1) can be used alone or in combination of two or more. It can also be used.
- the compound having two or more epoxy groups contained in the composition for forming a lower layer film for lithography of the present invention is not particularly limited as long as it is a compound having two or more epoxy groups.
- Examples include low molecular weight compounds having two or more epoxy groups (non-polymer compounds having a molecular weight of about 2000 or less) and polymers having two or more epoxy groups.
- Examples of low molecular weight compounds having two or more epoxy groups include 1,4 butanediol diglycidyl ether, 1,2 epoxy 4 (epoxyethyl) cyclohexane, glycerol triglycidyl ether, and diethylene glycol diglycidyl ether.
- Tetrabromobisphenol-A-diglycidyl ether bisphenol hexafluoroacetone diglycidyl ether, pentaerythritol diglycidyl ether, tris ginseng and the like.
- low molecular weight compounds having two or more epoxy groups include compounds having two or more hydroxyl groups or carboxyl groups such as diol compounds, triol compounds, dicarboxylic acid compounds and tricarboxylic acid compounds. And compounds having two or more glycidyl ether structures or daricidyl ester structures, which can be produced from glycidyl compounds such as epichlorohydrin.
- the molecular weight of the low molecular weight compound having two or more epoxy groups is preferably 200 or more. If the molecular weight force is smaller than this, a problem of sublimation during firing for forming the lower layer film may occur.
- the molecular weight is, for example, 200 to 2000, or 250 to 1500, or 300 to 1000, or 400 to 800.
- a compound having two or more epoxy groups needs to have two or more epoxy groups that are reaction sites at the time of forming the lower layer film from the viewpoint of forming a strong lower layer film. It is preferable to use a compound having 2 to 6 or 3 to 4 epoxy groups.
- polymers having two or more epoxy groups contained in the composition for forming a lower layer film for lithography of the present invention various polymers having an epoxy group without particular limitation can be used.
- Examples of such a polymer include a polymer that can be produced using an addition polymerizable monomer having an epoxy group.
- an addition-polymerizable monomer having an epoxy group and the above acrylate ester compound, methacrylic acid ester compound, acrylamide compound, methacrylamide compound, vinyl compound, styrene compound, maleimide compound, maleic acid Combined with other addition polymerizable monomers such as anhydride and acrylonitrile Mention may be made of polymers produced in combination.
- Examples of the addition polymerizable monomer having an epoxy group include glycidyl acrylate and glycidyl methacrylate.
- Examples of the polymer having two or more epoxy groups include a polymer having a structure represented by the formula (3) as a unit structure. Such a polymer can be made using glycidyl acrylate or glycidyl methacrylate. Examples thereof include polydaricidyl acrylate, polyglycidyl methacrylate, and a copolymer of glycidyl acrylate and glycidyl methacrylate.
- glycidyl atylate or glycidinole methacrylate and the above-mentioned acrylic ester compound, methacrylic ester compound, acrylamide compound, methacrylamide compound, vinyl compound, styrene compound, maleimide compound, maleic acid Mention may be made of polymers produced by combining anhydrides and other addition polymerizable monomers such as acrylonitrile.
- Examples include copolymers of glycidyl methacrylate and methacrylate compounds, copolymers of glycidyl methacrylate and acrylamide compounds, copolymers of glycidyl methacrylate and methacrylate compounds, copolymers of glycidyl methacrylate and acrylate compounds, acrylic acid Copolymer of glycidyl acrylate and styrene, copolymer of glycidyl acrylate and styrene, copolymer of glycidyl acrylate and butyl, copolymer of glycidyl acrylate and methacrylate, and copolymer of glycidyl acrylate and maleimide Etc.
- Addition polymerizable monomer Z Other addition polymerizable monomer as, for example, 100Zl to lZlOO, or 50Zl to lZ50, or 10Z1 to: LZ10, preferably 5Zl to lZ5, or 3Zl to lZ3 It is.
- polymers having two or more epoxy groups examples include polymers that can be produced by a reaction between a polymer having a hydroxyl group and a compound having an epoxy group such as epichlorohydrin or glycidyl tosylate.
- epoxy phenol novolac manufactured from phenol novolac and epichlorohydrin, and other epoxy crezo One novolak, epoxy naphthol novolak, etc. are mentioned.
- the weight average molecular weight of the polymer is, for example, 1000 to 500,000, for example, 1000 to 200,000. Or 3000 to 150000, or 3000 to 50000.
- Examples of the compound having two or more epoxy groups include amino acid-containing epoxy resins YH-434 and YH434L (manufactured by Tohto Kasei Co., Ltd.), and epoxide, an epoxy resin having a cyclohexene oxide structure.
- the compound having two or more epoxy groups can be used alone or in combination of two or more.
- the content ratio of the compound having two or more protected carboxyl groups represented by the formula (1) and the compound having two or more epoxy groups is expressed by mass ratio.
- a compound having two or more protected carboxyl groups represented by the formula (1) A compound having two or more Z epoxy groups, for example, 20Zl to l ⁇ 20, or 10 ⁇ 1 to: LZ10, or 5Zl to lZ5 Or 3/1 to 1Z3, or 2Zl to lZ2, or 3Z2 to 2Z3.
- Examples of the polymer having a protected carboxyl group represented by the formula (1), which is contained in the composition for forming a lower layer film for lithography of the present invention include polymers of the formulas (11) to (22). .
- the polymer of Formula (23)-Formula (30) can be mentioned, for example. (Wherein p, q and r represent the ratio of each unit structure to the total number of repeating unit structures constituting the polymer, and the sum thereof is 1)
- a light-absorbing compound, a surfactant, and a photoacid generator can be added to the underlayer film forming composition for lithography of the present invention.
- the light-absorbing compound has a high absorptivity with respect to light in the photosensitive characteristic wavelength region of the photosensitive component in the photoresist layer provided on the lower layer film, and a standing wave generated by reflection from the substrate, Any device that can prevent irregular reflection due to a step on the substrate surface can be used without particular limitation.
- Examples of such light-absorbing compounds include benzophenone compounds, benzotriazole compounds, azo compounds, naphthalene compounds, anthracene compounds, anthraquinone compounds, triazine compounds, and triazines.
- Trione compounds, quinolinic compounds and the like can be used. Naphthalene compounds, anthracene compounds, triazine compounds, and triazine trione compounds are used.
- naphthalenecarboxylic acid 2-naphthalenecarboxylic acid, 1 Naphthol, 2-naphthol, naphthyl acetic acid, 1-hydroxy 2-naphthalene carboxylic acid, 3 hydroxy-2 naphthalene carboxylic acid, 3, 7 dihydroxy-2 naphthalene carboxylic acid, 6 bromo-2 hydroxy naphthalene, 2, 6 naphthalene dicarboxylic acid, 9 anthracene Carboxylic acid, 10 Bromo 9 Anthracene carboxylic acid, Anthracene 1, 9, 10 Dicarboxylic acid, 1-anthracene carboxylic acid, 1-hydroxyanthracene, 1, 2, 3 anthracentriol, 2, 7, 9 anthracentriol, benzoic acid, 4 Hydroxybenzoic acid, 4 Bromobenzoic acid, 3 Rhodobenzoic acid, 2, 4, 6 Tribromophenol, 2, 4, 6 Tribro
- Examples of the light-absorbing compound include a polymer having a benzene ring, naphthalene ring or anthracene ring structure.
- light-absorbing compounds can be used alone or in combination of two or more forces.
- the addition amount thereof is 20% by mass or less in the solid content, for example, 0.1 to 20% by mass, or 1 to 10% by mass. 0/0.
- the underlayer film forming composition for lithography of the present invention can contain a surfactant.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, and the like.
- Polyoxyethylene alkylaryl ethers such as polyoxyethylene nonylphenol ether, polyoxyethylene polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, Sorbitan fatty acid esters such as sorbitan trioleate and sorbitan tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Nso sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan fatty acid esters such as polyoxyethylene sorbitan tristearate Bruno - one Surfactants, F-top EF301, EF303, EF352 (manufactured by Tochem Products), MegaFuck F171, F173 (manufactured by Dainippon Ink and Chemicals), Florard FC430, FC43 1 (Sumitomo 3EM) ),
- a photoacid generator can be added in order to make the acidity of the photoresist and the lower layer film that are covered by the upper layer in the lithography process coincide.
- the photoacid generator include form salt compounds, sulfonimide compounds, disulfonyl diazomethane compounds, and the like.
- salt salts include diphenol-hexahexafluorophosphate, disulfide-sulfur-umtrifnoroleolomethanes norephonate, diphloe-nodonnonafnoleo rononoremanolebutannorenonate , Diphenenoreonium perfunoreoronoremanoleo octane sulfonate, diphenol rhodonyum camphor sulfonate, bis (4-tert-butylphenol) oodo-umcamphor sulfonate and bis (4 —Tert-butylphenol) ododonium salt compounds such as ododonium trifluoromethanesulfonate, and triphenol-nolesnoreform hexafnoreo oral antimonate, trifene-nolesnorephonium nonaf noreorono noremanolev Tansnor
- sulfonimide compounds include N— (trifluoromethanesulfo-loxy) succinimide, N— (nonafluoro-normalbutanesulfo-loxy) succinimide, N (camphorsulfo-loxy) succinimide and N (trifluoromethanesulfo- (Luoxy) naphthalimide and the like.
- disulfo-diazomethane compounds include bis (trifluoromethylsulfo) diazomethane, bis (cyclohexylsulfo) diazomethane, and bis (phenolsulfo).
- -L) diazomethane bis (p-toluenesulfol) diazomethane, bis (2,4 dimethylbenzenesulfol) diazomethane, and methylsulfo-l-p-toluenesulfol diazomethane.
- photoacid generators can be used alone or in combination of two or more.
- the content thereof is, for example, 20% by mass or less, 0.01 to 10% by mass, or 0.1 to 10% by mass in the solid content of the lower layer film-forming composition. 5% by mass, or 0.5-3% by mass.
- a rheology adjusting agent, an adhesion aid and the like can be added to the composition for forming a lower layer film for lithography according to the present invention, if necessary.
- the rheology modifier is effective for improving the fluidity of the lower layer film-forming composition, and particularly for enhancing the filling property of the lower layer film-forming composition into the holes in the firing step.
- Adhesion aids are effective in improving the adhesion between the semiconductor substrate or photoresist and the underlayer film, and in particular, suppressing the peeling of the photoresist during development.
- the solvent used is not particularly limited as long as it is a solvent capable of dissolving the solid content.
- a solvent include, for example, methyl acetate sorb acetate, ethyl acetate sorb acetate, propylene glycol monole, propylene glycol monomethyl ether, propylene glycol monobutino reeenoate, propylene glycol monomethyl ether acetate, propylene glycol monoethanolate.
- the present invention is applied to a semiconductor substrate (for example, silicon-dioxide-silicon-coated substrate, silicon wafer substrate, silicon nitride substrate, glass substrate, and substrate) by an appropriate coating method such as a spinner or a coater.
- the lower layer film-forming composition for lithography is applied, and then the lower layer film is formed by baking.
- the firing conditions include firing temperature Medium strength at 80 ° C to 250 ° C, firing time 0.3 to 60 minutes, appropriately selected.
- the firing temperature is 130 ° C to 250 ° C, and the firing time is 0.5 to 5 minutes.
- the thickness of the lower layer film is, for example, 0.01 to 3. O / zm, for example, 0.03 to: LO / zm, or 0.05 to 0.50 ⁇ m. .
- the composition for forming a lower layer film for lithography of the present invention comprises a compound having a protected carboxyl group represented by formula (1) and a compound having an epoxy group.
- the lower layer film is an organic solvent commonly used in a photoresist composition applied to the upper layer, for example, ethylene glycolenomonomethyl ether, ethenorecellosolve acetate, diethylene glycol monomer.
- Ethinoreethenole propylene glycolenole, propyleneglycololemonomethinoleate, propyleneglycolenomonomethinoreatenoacetate, propylene glycol propyl ether acetate, toluene, methyl ethyl ketone, cyclohexanone, 2-hydroxyl Low solubility in ethyl ethyl propionate, 2-hydroxy 2-methyl ethyl propionate, ethoxy ethyl acetate, methyl pyruvate, ethyl lactate and butyl lactate.
- the underlayer film formed from the underlayer film forming composition of the present invention does not cause intermixing with the photoresist. Further, when a compound having many reaction sites is used, it is considered that the lower layer film to be formed becomes stronger.
- a polymer is used as a compound having a protected carboxyl group represented by the formula (1) or a compound having an epoxy group, a cross-linked structure is formed by a reaction during firing, and the lower layer film is stronger. It is thought that it becomes. Therefore, in the underlayer film forming composition of the present invention, it is more preferable to use a polymer having a protected carboxyl group or a polymer having an epoxy group represented by the formula (1).
- the formation of a carboxyl group by thermal decomposition of the protected carboxyl group represented by the formula (1) and the reaction between the carboxyl group and the epoxy group thus generated proceed easily under firing conditions. Does not require a catalyst. Therefore, it is particularly necessary to add a crosslinking catalyst such as an acid compound contained in the conventional composition for forming a crosslinkable underlayer film to the underlayer film forming composition for lithography of the present invention. And not. Therefore, the composition for forming a lower layer film for lithography of the present invention is excellent in storage stability.
- Formation of the photoresist layer can be carried out by a well-known method, that is, by applying a photoresist composition solution onto the lower layer film and heating.
- the photoresist applied and formed on the lower layer film of the present invention is sensitive to exposure light.
- a negative photoresist or a positive photoresist can be used.
- a chemically amplified photoresist consisting of a low molecular weight compound that decomposes with an acid to increase the alkali dissolution rate of the photoresist and an alkali-soluble binder and a photoacid generator, and has a group that decomposes with an acid to increase the alkali dissolution rate.
- photoresists consisting of a photoacid generator and a low molecular weight compound that decomposes with a binder and acid to increase the alkali dissolution rate of the photoresist.
- APEX—E Sumitomo Chemical Co., Ltd.
- Product name PAR710 manufactured by Shin-Etsu Chemical Co., Ltd.
- Product name SEPR430 etc.
- a KrF excimer laser (wavelength 248 nm), an ArF excimer laser (wavelength 193 nm), an F2 excimer laser (wavelength 157 nm), or the like can be used.
- post-exposure bake can be performed as necessary.
- the post-exposure heating is appropriately selected from a heating temperature of 70 ° C to 150 ° C and a heating time of 0.3 to 10 minutes.
- photoresist developer For example, when a positive photoresist is used, the exposed portion of the photoresist is removed, and a photoresist pattern is formed.
- Developers for photoresists include aqueous solutions of alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, hydroxide tetramethylammonium, hydroxide tetratetrammonium.
- alkaline aqueous solutions such as aqueous solutions of quaternary ammonium hydroxides such as ammonium and choline, and aqueous amine solutions such as ethanolamine, propylamine, and ethylenediamine.
- a surfactant or the like can be added to these developers.
- a temperature of 5 to 50 ° C and a time of 10 to 300 seconds are also appropriately selected.
- the lower layer film is removed and the semiconductor substrate is processed.
- the removal of the lower layer film is done by tetrafluoromethane, perfluorocyclobutane (C F), perfluoropropane (C F), trifluorometa
- Carbon monoxide, argon, oxygen, nitrogen, sulfur hexafluoride, difluoromethane, trifluoride This is performed using a gas such as nitrogen and chlorine trifluoride.
- An organic antireflection film layer may be applied and formed before or after the lower layer film of the present invention is formed on the semiconductor substrate.
- the antireflective coating composition used there is not particularly limited and can be arbitrarily selected from those conventionally used in the lithography process, and can be used by a conventional method such as a spinner. 1.
- An antireflection film can be formed by coating and baking with a coater. Examples of the antireflective film composition include a light-absorbing compound, a polymer and a solvent as main components, a polymer having a light-absorbing group linked by a chemical bond, a cross-linking agent and a solvent as main components.
- These antireflective coating compositions can also contain an acid component, an acid generator component, a rheology modifier, etc., if necessary.
- the light-absorbing compound can be used as long as it has a high absorptivity with respect to light in the photosensitive characteristic wavelength region of the photosensitive component in the photoresist provided on the antireflection film. Examples include benzophenone compounds, benzotriazole compounds, azo compounds, naphthalene compounds, anthracene compounds, anthraquinone compounds, triazine compounds.
- polystyrene examples include polyester, polyimide, polystyrene, novolac resin, polyacetal, and acrylic polymer.
- polystyrene examples include polymers having a light-absorbing group linked by a chemical bond such as an anthracene ring, naphthalene ring, benzene ring, quinoline ring, quinoxaline ring, and thiazole ring.
- the semiconductor substrate to which the underlayer film forming composition of the present invention is applied may have an inorganic antireflection film formed on the surface thereof by a CVD method or the like.
- An underlayer film can also be formed.
- the underlayer film formed from the underlayer film forming composition of the present invention may also have absorption for the light depending on the wavelength of exposure light used in the lithography process. It can be used as a layer having an effect of preventing the reflected light from, that is, an antireflection film.
- the lower layer film of the present invention is a layer for preventing the interaction between the substrate and the photoresist.
- the lower layer film formed from the composition for forming a lower layer film for lithography of the present invention is applied to a substrate on which a via hole used in a dual machine process is formed, and is used as a filling material that can fill the hole without any gap. It can also be used as a flattening material for flattening the substrate surface.
- the glycidinoremetatalylate 10.OOg and methinoremetatalylate 28.16g were dissolved in 152.7g of cinnamate ethinole, nitrogen was passed through the solution for 30 minutes, and then the temperature was raised to 70 ° C. While maintaining the reaction solution at 70 ° C., 0.776 g of azobisisobutyryl-tolyl and 0.776 g of 1-dodecanethiol were added. After stirring for 8 hours at 70 ° C. under a nitrogen atmosphere, 0.1 g of 4-methoxyphenol was added to obtain a solution containing a copolymer of glycidyl and methyl metatalylate. As a result of GPC analysis of the obtained copolymer, the number average molecular weight Mn2400 was Mw6900 and the weight average molecular weight (in terms of standard polystyrene) was Mw6900.
- Methyl ethyl ketone (13.6 g) and 1, 3, 5 benzenecarboxylic acid (Wako Pure Chemical Industries, Ltd.) 5.
- OOg and Nonolemanole butinorevininoreethenore 8.58g were dissolved, 0.014g of phosphoric acid was added as an insect medium, and the mixture was stirred at 80 ° C for 8 hours under nitrogen atmosphere. Then, the solvent was distilled off to obtain 1,3,5-benzenetricarboxylic acid-tris (1 butoxetyl) ester.
- Tris (2-carboxyethyl) isocyanuric acid (Shikoku Kasei Kogyo Co., Ltd.) 5. 8.3 g of normal ethyl butyl ether is dissolved in 10.8 g of methyl ethyl ketone, and phosphoric acid is used as a catalyst. 0. Ol lg was added, and the mixture was stirred at 80 ° C. for 8 hours under a nitrogen atmosphere. Then, the solvent was distilled off to obtain tris (2- (1butoxy) ethyloxycarbonyl) isocyanuric acid (formula (33)).
- Synthesis Example solvent solution (solids concentration 20.0 wt 0/0) comprising a copolymer of glycidyl methacrylate Tari rate and methyl methacrylate Tali rate obtained in 1 10.
- Og propylene glycol monomethyl ether 4 75 g, Ethyl lactate 3.08 g, 1, 2, 4, 5 Benzenetetracarboxylic acid-tetrakis (1 butoxychetyl) ester 0. 460 g obtained in Synthesis Example 3, and surfactant R—30 (Dainippon Ink Chem. 0. OlOg was made into a 13.5 mass% solution. And it filtered using the polyethylene micro filter with the hole diameter of 0.05 m, and prepared the solution of the lower layer film formation composition for lithography.
- the solvent solution (solids concentration 20.0 wt 0/0) 10. 0g containing copolymer of glycidyl methacrylate Tari rate and methyl methacrylate Tali rate obtained in Synthesis Example 1, propylene glycol monomethyl ether 4. 75 g, lactic Echiru 3. 08 g, 1, 3, 5 benzenetricarboxylic acid, tris (1-butoxychetyl) ester 0. 460 g obtained in Synthesis Example 4, and surfactant R-30 (Dainippon Ink Chemical Co., Ltd.) 0. For example 13. was 5 mass 0/0 solution. Then, the solution was filtered using a polyethylene microfilter having a pore diameter of 0.05 m to prepare a solution of the lower layer film forming composition.
- the solvent solution (solids concentration 20.0 wt 0/0) 10. 0g containing copolymer of glycidyl methacrylate Tari rate and methyl methacrylate Tali rate obtained in Synthesis Example 1, propylene glycol monomethyl ether 4. 75 g, lactic Echiru 3. 08 g, tris (2- (1-butoxy) ethyloxyl group) isocyanuric acid 0.460 g obtained in Synthesis Example 5 and surfactant R-30 (manufactured by Dainippon Ink & Chemicals, Inc.) 0.0010 g added was 13.5 mass 0/0 solution. And it filtered using the polyethylene micro filter of the hole diameter 0.05 / zm, and prepared the solution of the lower layer film formation composition.
- Example 5 Solution containing copolymer of 1-ptochichetyl metatalylate and methyl metatalylate obtained in Synthesis Example 2 (solid concentration 20.0% by mass) 10. Og, 4.75 g of propylene glycol monomethyl ether, lactic acid Ethyl 3.08g, 4, 4'-methylenebis (N, N-diglycidyl-line) (product name YH434L, manufactured by Tohto Kasei Co., Ltd.) 0.460g and surfactant R-30 (Dainippon Ink Chemical ( Ltd.)) to 0. olog was mosquito ⁇ tut 13.5 mass 0/0 solution. And it filtered using the polyethylene micro filter with the hole diameter of 0.05 / zm, and prepared the solution of the lower layer film formation composition.
- Example 7 Solution obtained in Synthesis Example 2 containing a copolymer of 1 butoxetyl methacrylate and methyl methacrylate (solid concentration 20.0% by mass) 10.
- Og propylene glycol monomethyl ether 5.21 g, ethyl lactate 4 16 g, pentaerythritol tetraglycidyl ether (formula (35) manufactured by Nagase ChemteX Corp., trade name EX411) 0.70 g, and surfactant R-30 (manufactured by Dainippon Ink & Chemicals) 0. OlOg
- the solution was filtered using a polyethylene microfilter having a pore diameter of 0.05 ⁇ m to prepare a solution of the lower layer film forming composition.
- the solutions of the underlayer film forming compositions for lithography obtained in Examples 1 to 8 were each applied onto a silicon wafer substrate using a spinner. By baking on a hot plate at 205 ° C for 1 minute, a lower layer film (thickness 0.45 m) was formed. These underlayer films were immersed in ethyl lactate, a solvent used for photoresist, and confirmed to be insoluble.
- the solutions of the underlayer film forming compositions obtained in Examples 1 to 8 were respectively converted into silicon by a spinner. This was coated on a wafer substrate.
- a lower layer film (film thickness 0.45 m) was formed by baking at 205 ° C. for 1 minute on a hot plate.
- a commercially available photoresist solution (manufactured by Fuji Photo Film Co., Ltd., trade name GARS8105G1 and Shin-Etsu Igaku Kogyo Co., Ltd., trade name S EPR430) was applied to the upper layers of these lower layer films using a spinner. Heated on a hot plate at 90 ° C or 110 ° C for 1.5 minutes. After exposure of the photoresist, post-exposure heating was performed at 90 ° C. for 1.5 minutes. After developing the photoresist, the thickness of the lower layer film was measured, and it was confirmed that intermixing between the lower layer film and the photoresist layer did not occur.
- the solutions of the underlayer film-forming compositions obtained in Examples 1 to 8 were respectively formed on a silicon dioxide (SiO 2) wafer substrate having a hole (diameter 0.18 m, depth 1.0 m) using a spinner.
- the substrate used has a hole iso (rough) and dense (dense) pattern as shown in Fig. 1.
- the Iso (coarse) pattern is a pattern in which the distance from the hole center to the adjacent hole center is five times the diameter of the hole.
- the dense pattern is a pattern in which the distance from the hole center to the next hole center is one time the diameter of the hole.
- the depth of the hole is 1. O / z m and the diameter of the hole is 0.18 / z m.
- planarization rate by the lower layer film was evaluated by observing the cross-sectional shape of the substrate using a scanning electron microscope (SEM).
- SEM scanning electron microscope
- Difficult example 2 440 380 60 100 100 100 0
- Example 5 440 380 60 100 100 100 0
- Example 7 450 360 90 100 100 100 0
- Example 8 450 370 80 100 100 100 0
- the difference in film thickness (Bias) on the iso (coarse) and dense (dense) patterns of the lower layer films of Examples 1 to 8 is small.
- the underlayer films of Examples 1 to 8 are excellent in fluidity on a fine dense hole pattern where the film thickness is particularly difficult to be constant. This is because the number of holes per unit area (hole density) force on the hole substrate is larger than the iso part. Even in the dense part, the solution force of the underlayer film forming composition S flows smoothly into these many holes, and is constant. This is because the film thickness can be obtained. As a result, the difference in film thickness between the Iso part and the Dense part is small and the flatness ratio is large. Further, by using the underlayer film forming compositions of Examples 1 to 8, it was possible to achieve flattening regardless of the iso part and the dense part.
- Example 2 The solution of the underlayer film forming composition obtained in Example 1 was applied onto a silicon wafer substrate using a spinner. On the hot plate, it was baked at 205 ° C for 1 minute to form a lower layer film (film thickness 0.20 / zm). Then, when the refractive index (n value) and attenuation coefficient (k value) at a wavelength of 193 nm were measured for this lower layer film using a spectroscopic ellipsometer, the refractive index (n value) was 1.64 and the attenuation coefficient (k value) ) Was 0.04.
- the solution of the underlayer film forming composition obtained in Example 2 was applied onto a silicon wafer substrate using a spinner. Baking was performed at 205 ° C for 1 minute on a hot plate to form a lower layer film (film thickness 0.20 m). Then, when the refractive index (n value) and attenuation coefficient (k value) at a wavelength of 193 nm were measured for this lower layer film using a spectroscopic ellipsometer, the refractive index (n value) was 1.64. The number (k value) was 0.03.
- the dry etching rate (the amount of decrease in film thickness per unit time) was measured. The results are shown in Table 2.
- the dry etching selectivity indicates the dry etching rate of the lower layer film when the dry etching rate of a photoresist for KrF laser lithography (trade name SEPR430, manufactured by Shin-Etsu Chemical Co., Ltd.) is 1.0. .
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Abstract
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JP2006553858A JP4753046B2 (ja) | 2005-01-21 | 2006-01-06 | 保護されたカルボキシル基を有する化合物を含むリソグラフィー用下層膜形成組成物 |
CN2006800028015A CN101107569B (zh) | 2005-01-21 | 2006-01-06 | 含有具有被保护的羧基的化合物的形成光刻用下层膜的组合物 |
EP06702060A EP1850180A4 (en) | 2005-01-21 | 2006-01-06 | COMPOSITION FOR FORMING A LAYERING LINEOGRAPHY FILM CONTAINING A CARBOXYL PROTECTED COMPOSITION |
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Cited By (12)
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JP2009096884A (ja) * | 2007-10-17 | 2009-05-07 | Nof Corp | カラーフィルター保護膜用の熱硬化性樹脂組成物、およびカラーフィルター |
JP2011042645A (ja) * | 2009-05-20 | 2011-03-03 | Rohm & Haas Electronic Materials Llc | 上塗りフォトレジストと共に使用するためのコーティング組成物 |
JP2012515369A (ja) * | 2009-01-16 | 2012-07-05 | フジフィルム・エレクトロニック・マテリアルズ・ユーエスエイ・インコーポレイテッド | 半導体基板コーティングのための非ポリマーバインダー |
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US8481247B2 (en) * | 2006-08-28 | 2013-07-09 | Nissan Chemical Industries, Ltd. | Resist underlayer film forming composition containing liquid additive |
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JP2015207007A (ja) * | 2009-01-16 | 2015-11-19 | フジフィルム・エレクトロニック・マテリアルズ・ユーエスエイ・インコーポレイテッドFujiFilm Electronic Materials USA, Inc. | 半導体基板コーティングのための非ポリマーバインダー |
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JPWO2016158509A1 (ja) * | 2015-03-31 | 2018-01-25 | 日産化学工業株式会社 | カチオン重合性レジスト下層膜形成組成物 |
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US10854451B2 (en) | 2015-06-22 | 2020-12-01 | Brewer Science, Inc. | Superplanarizing spin-on carbon materials |
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JPWO2017191767A1 (ja) * | 2016-05-02 | 2019-03-07 | 日産化学株式会社 | 特定の架橋剤を含む保護膜形成組成物及びそれを用いたパターン形成方法 |
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Also Published As
Publication number | Publication date |
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EP1850180A1 (en) | 2007-10-31 |
TWI398733B (zh) | 2013-06-11 |
KR20070095320A (ko) | 2007-09-28 |
US10509320B2 (en) | 2019-12-17 |
CN101107569A (zh) | 2008-01-16 |
CN101107569B (zh) | 2011-06-15 |
KR101318182B1 (ko) | 2013-10-16 |
JPWO2006077748A1 (ja) | 2008-06-19 |
US20080102649A1 (en) | 2008-05-01 |
JP4753046B2 (ja) | 2011-08-17 |
EP1850180A4 (en) | 2009-12-30 |
TW200641543A (en) | 2006-12-01 |
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