WO2006070695A1 - レジスト保護膜形成用材料およびこれを用いたレジストパターン形成方法 - Google Patents
レジスト保護膜形成用材料およびこれを用いたレジストパターン形成方法 Download PDFInfo
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- WO2006070695A1 WO2006070695A1 PCT/JP2005/023637 JP2005023637W WO2006070695A1 WO 2006070695 A1 WO2006070695 A1 WO 2006070695A1 JP 2005023637 W JP2005023637 W JP 2005023637W WO 2006070695 A1 WO2006070695 A1 WO 2006070695A1
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- protective film
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- forming material
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1805—C5-(meth)acrylate, e.g. pentyl (meth)acrylate
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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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
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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
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
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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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
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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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
Definitions
- the present invention relates to a resist protective film forming material suitable for forming a protective film for a resist film, and a resist pattern forming method using the same.
- the present invention relates to a resist protective film forming material suitable for forming a protective film for a resist film, and a resist pattern forming method using the same.
- the present invention relates to a resist protective film forming material suitable for forming a protective film for a resist film, and a resist pattern forming method using the same.
- the present invention relates to a resist protective film forming material suitable for forming a protective film for a resist film, and a resist pattern forming method using the same.
- a lithography exposure light force S at least a predetermined thickness having a refractive index higher than air on the resist film and a lower refractive index than the resist film in the path reaching the resist film
- a resist protective film suitable for use in an immersion exposure process having a configuration in which the resolution of the resist pattern is improved by exposing the resist film in a state where the liquid (hereinafter referred to as immersion exposure liquid) is present.
- immersion exposure liquid a material and a resist pattern forming method using the protective film forming material.
- Lithography method is frequently used for the manufacture of fine structures in various electronic devices such as semiconductor devices and liquid crystal devices. With the miniaturization of device structures, the resist pattern has become finer in the lithography process. It is requested.
- the development points are generally such as shortening the wavelength of light sources such as EUV (extreme ultraviolet light), electron beam, X-ray, soft X-ray, and increasing the numerical aperture (NA) of the lens. .
- EUV extreme ultraviolet light
- X-ray electron beam
- X-ray soft X-ray
- NA numerical aperture
- Non-Patent Document 1 Non-patent Document 1
- Permitted document 2 Non-patent document 3
- an immersion exposure liquid such as pure water or a fluorine-based inert liquid having a predetermined thickness is interposed between at least the resist film and the resist film on the substrate during exposure.
- a light source having the same exposure wavelength is used by replacing the exposure optical path space, which has conventionally been an inert gas such as air or nitrogen, with a higher refractive index (n), liquid such as pure water.
- n refractive index
- Non-Patent Document 1 Journal of Vacuum Science & Technology B (J. Vac. Sci. Technol. B) ((Issuing country) Ameri force), 1999, 17th, 6 No., pages 3306-3309
- Non-Patent Literature 3 Proceedings of SPIE Vol.4691 (Proceedings of SPIE Vol.4691 ((Publishing country) USA) 2002, 4691, 459-465
- Patent Document 1 International Publication No. 2004/074937 Pamphlet
- Patent Document 1 a protective film forming material using a fluorine-containing resin has been proposed for the purpose of solving the above-described problems.
- Patent Document 1 a protective film forming material using a fluorine-containing resin.
- the above object can be achieved, but a special cleaning solvent and a coating device are required, and the number of steps for removing the protective film is increased. The above problem occurs.
- the present invention provides a technique capable of applying a resist film obtained from a conventional resist composition established by spending many development resources to immersion exposure and further effectively suppressing surface defects. It is to be an issue.
- a protective film forming material capable of effectively suppressing surface defects in an immersion exposure process in which an immersion exposure liquid is disposed on an exposed film. More specifically, the immersion exposure liquid adhering to the substrate after exposure can be easily removed, the substrate edge can be exposed smoothly, the exposure process can be performed smoothly, and the immersion exposure.
- a material for forming a protective film is provided that does not cause a change in the resist film during immersion exposure by the liquid for use and a refractive index fluctuation caused by the change in the liquid for immersion exposure due to the elution component from the resist film. There is.
- a resist protective film forming material is a resist protective film forming material containing an alkali-soluble polymer component for forming an upper protective film of a resist film.
- the contact angle between the polymer component and water is 90 ° or more It is characterized by that.
- the resist pattern forming method according to the present invention is a resist pattern forming method using an immersion exposure process, wherein a photoresist film is formed on a substrate, and the protective film is formed on the resist film.
- a protective film having characteristics that are substantially compatible with water and capable of being alkali is formed, and the resist film and the protective film are stacked.
- a liquid for immersion exposure having a predetermined thickness is disposed at least directly on the protective film, and the resist film is irradiated with a predetermined pattern light through the liquid for immersion exposure and the protective film, and heat treatment is performed as necessary. And removing the protective film by washing the protective film and the resist film using an alkaline developer, and simultaneously developing the resist film to obtain a resist pattern. That.
- the protective film-forming material according to the present invention can be directly formed on the resist film, and does not hinder pattern exposure, and the protective film-forming material of the present invention is insoluble in water. Therefore, “water (pure water or deionized water) that is regarded as the most promising liquid for immersion exposure because it has no optical requirements for immersion exposure, ease of handling, and environmental pollution” It can be used as a liquid for immersion exposure. In other words, even if water that is easy to handle, has good refractive index characteristics, and has no environmental pollution property is used as a liquid for immersion exposure, while resist films having various compositions are subjected to the immersion exposure process, It is possible to obtain a resist pattern with sufficient protection and good characteristics.
- the immersion exposure liquid when an exposure wavelength of 157 nm is used as the immersion exposure liquid, fluorinated solvents are considered promising in terms of absorption of exposure light, and this is the case when such fluorinated solvents are used.
- the resist film can be sufficiently protected during the immersion exposure process, and a resist pattern with good characteristics can be obtained.
- the protective film forming material according to the present invention is soluble in the strength of the Al, the resist film strength is removed before the development process even after the exposure is completed and the development process is completed. There is no need to do.
- the protective film obtained using the protective film-forming material of the present invention is soluble in alkali, an alkaline developer of a resist film that does not require a protective film removal step before the development process after exposure.
- the development process can be carried out with the protective film remaining, thereby removing the protective film and resist.
- the development of the film can be realized at the same time. Therefore, the pattern forming method performed using the protective film forming material of the present invention can efficiently form a resist film with good pattern characteristics with extremely low environmental pollution and a reduced number of steps. it can.
- the protective film-forming material of the present invention has a high contact angle with the immersion exposure liquid disposed on the film to be exposed, it is easy to remove the immersion exposure liquid after exposure. Therefore, the risk of occurrence of surface defects can be suppressed, and furthermore, the edge of the substrate can be exposed smoothly.
- the protective film forming material of the present invention can simultaneously prevent the resist film from being invaded by the immersion exposure liquid and the alteration of the immersion exposure liquid itself due to the components eluted from the resist film.
- the resist protective film-forming material according to the present invention is a resist protective film-forming material containing an alkali-soluble polymer component for forming an upper protective film of a resist film, the polymer
- the contact angle between components and water is 90 ° or more.
- the material for forming a resist protective film according to the present invention has a contact angle of 90 ° or more with respect to the liquid for immersion exposure used in the liquid immersion exposure process, so that it is less susceptible to erosion by the liquid for liquid immersion exposure with low wettability. .
- the resist protective film-forming material does not have substantial compatibility with water, is soluble in alkali, and is transparent to exposure light. Mixing does not occur in between, and the adhesion to the resist film is good and the solubility in the developer is good.
- the polymer component is preferably an acrylic polymer. It is considered that the additional characteristic required for the protective film for immersion exposure requires that the contact angle with respect to the immersion exposure liquid has a value equal to or greater than a predetermined value.
- the film formed by using the acrylic polymer has a contact angle of 90 ° or more with respect to water. Therefore, as described above, the film is strong if it is not easily eroded by the immersion exposure liquid having low wettability. Immersion exposure on the protective film The amount of adhering light liquid decreases, cleaning time after immersion exposure processing is reduced, and unnecessary discharge of immersion exposure liquid out of the system Reduces the exposure of the substrate edge smoothly It also has the advantage that it can be done and is economical.
- the contact angle is 90 ° or more, and when the immersion exposure liquid is placed on the protective film, the immersion exposure liquid is appropriately repelled, and the physical stability as the immersion exposure liquid. Can be prevented.
- the “alkali-soluble polymer” suitable as the base polymer of the protective film-forming material of the present invention includes a (meth) acrylic acid structural unit and an acrylic acid ester represented by the following general formula (1). It is preferable to include at least a structural unit.
- the (meth) acrylic acid structural unit is a structural unit that imparts alkali solubility.
- R ′ represents a hydrogen atom, a methyl group, or a hydroxyl group having 1 to 4 carbon atoms.
- R m represents a linear or branched alkylene group having 1 to 5 carbon atoms.
- R f represents a hydrogen atom or an alkyl group having 1 to 15 carbon atoms, and a part or all of the hydrogen atoms of the alkyl group may be substituted with a fluorine atom.
- R m examples include linear alkylene groups such as a methylene group, n-ethylene group, n-propylene group, n-butylene group, and n-pentylene group; 1 methylethylene group, 1 It is possible to enumerate branched alkylene groups such as methylpropylene group and 2-methylpropylene group. Among these, a methylene group and an n-ethylene group are preferable.
- R f examples include those in which part or all of the hydrogen atoms of the lower alkyl group are replaced with fluorine atoms. Specifically, trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, undecafluoropropyl group, heptadecafluorooctyl group, etc. Is mentioned. Among these, the contact with water is high. From the point of view, heptadecafluorooctyl group is preferred.
- the acrylic polymer is at least one third structural unit represented by the following general formula (2) in the (meth) acrylic acid structural unit and the structural unit represented by the general formula (1).
- Addition of an acrylate ester structural unit is preferable from the viewpoints of excellent water resistance, imparting appropriate flexibility to the film, and improving transparency.
- R is a hydrogen atom or a methyl group
- R ′′ is an alicyclic hydrocarbon group having 4 to 15 carbon atoms.
- R " is composed of at least two structural units having R” a or R “ b, and R" a is a polycyclic hydrocarbon group, and R " b is preferably a monocyclic hydrocarbon group, which improves water resistance and transparency by introducing a polycyclic hydrocarbon group and a monocyclic hydrocarbon group, and introduces a chain hydrocarbon group to form a membrane.
- R " b is preferably a monocyclic hydrocarbon group, which improves water resistance and transparency by introducing a polycyclic hydrocarbon group and a monocyclic hydrocarbon group, and introduces a chain hydrocarbon group to form a membrane.
- the polycyclic hydrocarbon group includes at least one carbon selected from a dicyclopentanyl group, an adamantyl group, a norbornyl group, an isobornyl group, a tricyclodecyl group, and a tetracyclododecyl group.
- a hydrogen group is preferred.
- the monocyclic hydrocarbon group is preferably at least one hydrocarbon group selected from a cyclohexenole group, a cyclopentyl group, and a cyclopentyl group.
- the acrylic polymer is represented by the following general formula (3) in the (meth) acrylic acid structural unit, the structural unit represented by the general formula (1), and the structural unit represented by the general formula (2). It is preferable that an acrylic ester structural unit which is at least one kind of the fourth structural unit is added.
- R ′′ ′ is a chain hydrocarbon group.
- the chain hydrocarbon group may be at least one hydrocarbon group selected from n-butyl group, n-pentyl group, 2-ethyl hexyl group, and n-xyl group. preferable.
- the acrylic polymer is preferably represented by the following general formula (4).
- This acrylic polymer has a polycyclic hydrocarbon group, a monocyclic hydrocarbon group, and a chain hydrocarbon group attached to it, so that water resistance and transparency are improved, and the film has appropriate flexibility. Can be granted.
- q r s t and u represent the mol% content of each structural unit, and are each 260 mol%.
- the acrylic polymer as described above can be synthesized according to a known acrylic polymer polymerization method.
- the polystyrene equivalent weight average molecular weight by GPC of the resin of the polymer component is not particularly limited, but is S5000 80000, more preferably 8000 50000. It is.
- the polymer is soluble in an alcohol-based solvent and can be formed into a film by a spin coater.
- the polymer is swelled and reduced with respect to pure water within a sufficient time necessary for immersion exposure. And is soluble in an alkaline developer. That is, it has high suitability as a resist protective film material for immersion exposure.
- this polymer has a high refractive index of about 1.65 when it transmits 193 nm wavelength light.
- the protective film of the present invention is characterized by further containing a solvent. This solvent needs to dissolve the talyl polymer.
- any solvent that can dissolve the polymer can be used.
- solvents include alcohol solvents, paraffin solvents, fluorine solvents, and the like.
- alcohol solvent conventional alcohol solvents such as isopropyl alcohol, 1_hexanol, 2-methino _1_propanol, 4-methino _2_pentanol, etc. can be used, especially 2-methyl-1 propylene. Nord, 4-methyl-2-pentanol is preferred. It has been confirmed that n-pentane can be used as a paraffinic solvent and perfluoro-2-butyltetrahydrofuran can be used as a fluorinated solvent. Of these, alcohol solvents are preferred from the viewpoint of alkali solubility during development.
- the material for forming a resist protective film according to the present invention can further contain a crosslinking agent and an acidic compound.
- crosslinking agent for the protective film of the present invention any crosslinking agent that is soluble in the solvent can be used.
- a nitrogen-containing compound having an amino group and / or an imino group substituted with a hydroxyalkyl group and / or an alkoxyalkyl group it is possible to suitably use a nitrogen-containing compound having an amino group and / or an imino group substituted with a hydroxyalkyl group and / or an alkoxyalkyl group.
- the nitrogen-containing compound is preferably at least one selected from melamine derivatives, guanamine derivatives, glycoluril derivatives, succinilamide derivatives, and urea derivatives.
- these nitrogen-containing compounds include, for example, the above melamine compounds, urea compounds, guanamine compounds, acetoguanamine compounds, benzoguanamine compounds, Glycoluril compounds, succinylamide compounds, ethyleneurea compounds, etc., can be reacted with formalin in boiling water and treated with methylol, or further added to lower alcohols, specifically methanol, It can be obtained by reacting with ethanol, n-propanol, isopropanol, n -butanol, isobutanol, etc. to alkoxylate.
- tetrabutoxymethylated glycoluril is more preferably used.
- a condensation reaction product of a hydrocarbon compound substituted with at least one hydroxyl group and Z or alkyloxy group and a monohydroxymonocarboxylic acid compound can also be used suitably.
- the monohydroxymonocarboxylic acid those in which a hydroxyl group and a carboxyl group are bonded to the same carbon atom or two adjacent carbon atoms are preferable.
- the protective film-forming material of the present invention may further contain an acidic component (preferably a fluorocarbon compound).
- an acidic component preferably has a holding and stabilizing effect.
- fluorine-containing compounds that bring about the above-mentioned action are shown below. These fluorine-containing compounds are not subject to the Important New Use Regulation (SNUR) and are usable chemical substances.
- SNUR Important New Use Regulation
- n is an integer of 1 to 5
- n is an integer of 10 to 15
- R a is substituted one part or all of the fluorine atoms is, Ru alkyl group, is a substituted hydroxyl group, an alkoxy group, a carboxyl group, an amino group
- a fluorine-containing compound represented by the following formula:
- the fluorine-containing compound represented by these is suitable.
- the fluorine-containing compound represented by these is suitable.
- the fluorine-containing compound represented by the general formula (8) is preferably a fluorine-containing compound represented by the following chemical formula (13).
- the immersion exposure process is performed by exposing the resist film in a state where an immersion exposure liquid is interposed on at least the resist film along a path until the lithography exposure light reaches the resist film. It is a feature that improves the resolution of the pattern.
- the exposure light for exposing the resist film is preferably light having a main wavelength of 157 nm, 193 nm, or 248 ⁇ m.
- the immersion exposure can be performed by using water or a fluorine-based inert liquid that is substantially pure water or deionized water as the immersion exposure liquid.
- water is a more suitable immersion exposure liquid in consideration of cost, ease of post-processing, low environmental pollution, etc., but when 157 nm exposure light is used.
- the protective film formed from the protective film-forming material of the present invention is dense and suppresses invasion of the resist film by the liquid for immersion exposure, and further prevents permeation of environmental amine components, thereby preventing the resist.
- the necessary “retention resistance” can be imparted to the membrane.
- a resist film that can be used in the present invention is obtained using a conventionally used resist composition. Any resist film that can be used can be used, and it is not necessary to use it in a particularly limited manner. This is the greatest feature of the present invention.
- the protective film formed of the resist protective film forming material of the present invention is water-insoluble and has high strength and resistance to other immersion exposure liquids. It can be applied to resist films of any composition including low resist and resist films that are resistant to liquids. Therefore, as the resist film material of the present invention, any known resist can be used, and a conventional positive photoresist or negative photoresist can be used.
- a conventional resist composition is coated on a substrate such as a silicon wafer with a spinner and then pre-beta (PAB treatment) is performed.
- PAB treatment pre-beta
- a two-layer laminate in which an organic or inorganic antireflection film is provided between the substrate and the coating layer of the resist composition can also be used.
- the steps so far can be performed using a known method.
- the operating conditions and the like are preferably set as appropriate according to the composition and characteristics of the resist composition to be used.
- the material composition for forming a protective film according to the present invention represented by the chemical formula (4) above is used.
- a resist protective film is formed by uniformly applying the product and then curing it.
- a liquid for immersion exposure (for example, pure water, deionized water, a fluorine-based solvent, or a silica-based solvent) is disposed on the substrate on which the resist film covered with the protective film is formed in this manner.
- the liquid for immersion exposure for example, pure water, deionized water, a fluorine-based solvent, or a silica-based solvent
- the resist film on the immersed substrate is selectively exposed through a desired mask pattern. Accordingly, at this time, the exposure light passes through the immersion exposure liquid and the protective film and reaches the resist film.
- the resist film is shielded from the immersion exposure liquid such as pure water by the protective film. It is also possible to elute the components in the immersion exposure liquid and alter the optical characteristics such as the refractive index of the immersion exposure liquid itself.
- the wavelength used for exposure in this case is not particularly limited. ArF excimer laser, KrF excimer laser, F excimer laser, EUV (extreme ultraviolet), VUV (vacuum ultraviolet), electron beam, X-ray, soft It can be performed using radiation such as X-rays. This is mainly determined by the characteristics of the resist film.
- the liquid for immersion exposure is disposed on the resist film via the protective film at the time of exposure.
- the resist film is invaded by contact with the liquid for immersion exposure, but this invasion can be prevented by using the protective film of the present invention.
- immersion exposure liquid include water (pure water, deionized water), or a fluorine-based inert liquid.
- the fluorinated inert liquid include liquids mainly composed of fluorinated compounds such as CHCF, CFOCH, CFOCH, CHF.
- water (pure water or deionized water) is preferably used from the viewpoints of cost, safety, environmental problems, and versatility.
- exposure light having a wavelength of 157 nm is used, exposure is performed. From the viewpoint of low light absorption, it is preferable to use a fluorine-based inert liquid.
- the refractive index of the immersion exposure liquid to be used is not particularly limited as long as it is within the range of "greater than the refractive index of air and smaller than the refractive index of the resist composition used". Les.
- the substrate is taken out of the immersion exposure liquid, or the immersion exposure liquid is removed from the substrate. This is followed by the next step of developing with an alkaline developer, but before that, the resist film is heated to promote curing of the exposed portion. If the resist film is infiltrated by environmental amine components during this time, the pattern shape after the development process will be greatly degraded. However, in the present invention, since the protective film is densified, the environmental amine component does not invade the resist film.
- PEB post-exposure heating
- alkali development comprising an alkaline aqueous solution.
- the developing solution used for this development processing is alkaline
- the protective film is flowed by a solution
- the soluble portion of the resist film is flowed by a solution.
- post-beta may be performed following the development processing. And preferably using pure water And rinse. In this water rinse, for example, water is dropped or sprayed on the surface of the substrate while rotating the substrate to wash away the developer on the substrate and the protective film component and resist composition dissolved by the developer.
- the removal of the protective film and the development of the resist film can be realized simultaneously by a single development process.
- a resist pattern with a fine line width particularly a line-and-space pattern with a small pitch
- the pitch in the line-and-space pattern refers to the total distance of the resist pattern width and the space width in the line width direction of the pattern.
- the polymerization reaction solution was aged at 80 ° C. for 4 hours as it was, and then the polymerization reaction solution was heated until the reflux of the solvent was observed, and aged for 1 hour to complete the polymerization.
- a copolymer polymer represented by 14) was obtained.
- the resulting polymerization reaction solution had a solid content concentration of 20.2% and a weight average molecular weight (Mw) of 20,000 in terms of polystyrene.
- the following resin component, acid generator, and nitrogen-containing organic compound were uniformly dissolved in an organic solvent to prepare a resist composition.
- the resin component 100 parts by mass of a copolymer composed of structural units represented by the following chemical formula (15) was used.
- triphenylsulfonium nonafluorobutane sulfonate 2 triphenylsulfonium nonafluorobutane sulfonate 2.
- organic solvent propylene glycol monomethyl ether and propylene A 7.0% strength aqueous solution of a mixed solvent of glycol monomethyl ether acetate (mixing ratio 6: 4) was used.
- nitrogen-containing organic compound 0.25 parts by mass of triethanolamine was used. Furthermore, 25 parts by mass of ⁇ -petit-mouth rataton was added as an additive.
- a resist pattern was formed using the resist composition produced as described above.
- ARC29A organic antireflective coating composition
- an organic antireflection film having a thickness of 77 nm was formed.
- the resist composition is applied onto the antireflection film by using a spinner, pre-betaed at 130 ° C. for 90 seconds on a hot plate, and dried to have a film thickness of 225 nm on the antireflection film.
- the resist film was formed.
- pattern light was irradiated (exposed) using an ultraviolet ray (wavelength: 193 nm) by an immersion exposure apparatus AS 3—IML (manufactured by Canon Inc.) through the mask pattern.
- an 8-inch silicon wafer was used to form a 130 nm line and space pattern.
- PEB treatment was performed at 115 ° C for 90 seconds. After this PEB treatment, the film was developed with an alkaline developer at 23 ° C for 60 seconds with the protective film remaining. It is an alkaline developer, 2. using 38 mass 0/0 tetramethylammonium Niu arm hydroxide aqueous solution. This development process completely removed the protective film, successfully developed the resist film, and formed a good rectangular 130 nm line and space pattern.
- KLA measurement was performed with a surface patterning defect measuring apparatus (KLA Concor Corp .: KLA) for the pattern thus obtained, and the pattern defects were observed.
- the number of pattern defects peculiar to the immersion exposure process typified by a bridge was measured three times, and the average value was obtained.
- the obtained results are shown in Table 1 below as a ratio to the number of defects 100 obtained in Comparative Example 1 described later.
- Example 1 as the protective film-forming material, the copolymer represented by the chemical formula (14) obtained in Production Example 1 and 0.7% by mass of (CF 3) based on the copolymer were used. Except for using (SO) NH and adding a solid mass concentration of 2.5% by mass, the number of pattern defects typified by bridges was measured three times using the same method. The average value was obtained. The obtained results are shown in Table 1 below as a ratio to the number of defects 100 obtained in Comparative Example 1 described later.
- Example 1 as the protective film-forming material, the copolymer represented by the chemical formula (14) obtained in Production Example 1 and 0.7% by mass of (CF 3) based on the copolymer were used.
- (SO 3) NH and 0.7% by mass of tetrabutoxymethylated glycoluril with respect to the copolymer were added, and a composition having a solid content mass concentration of 2.5% by mass was used.
- Example 1 In Example 1, except that no protective film was formed on the resist film, the number of pattern defects represented by bridges and the like was measured three times, and the average value was obtained. The obtained results are shown in Table 1 below as a percentage of the number of defects obtained in Comparative Example 1 described later.
- any conventional resist composition can be used to form a resist film, and the immersion exposure liquid can be used in an immersion exposure process.
- Resist which can simultaneously prevent the occurrence of surface defects such as bridges and infiltration of the resist film by immersion exposure liquid, even when using water or fluorine-based inert liquids.
- a protective film forming material can be provided. Therefore, when the resist protective film forming material of the present invention is used, it is possible to effectively form a resist pattern using an immersion exposure process.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Engineering & Computer Science (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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EP05819797A EP1840655A4 (en) | 2004-12-27 | 2005-12-22 | MATERIAL FOR FORMING RESIST PROTECTIVE FILMS AND PROCESS FOR FORMING RESIST PATTERN THEREWITH |
US11/722,797 US8278025B2 (en) | 2004-12-27 | 2005-12-22 | Material for forming resist protection films and method for resist pattern formation with the same |
TW094146790A TW200641542A (en) | 2004-12-27 | 2005-12-27 | Material for forming resist protective film and resist pattern forming method using the same |
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JP2004-378234 | 2004-12-27 | ||
JP2004378234A JP4322205B2 (ja) | 2004-12-27 | 2004-12-27 | レジスト保護膜形成用材料およびこれを用いたレジストパターン形成方法 |
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WO2006070695A1 true WO2006070695A1 (ja) | 2006-07-06 |
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PCT/JP2005/023637 WO2006070695A1 (ja) | 2004-12-27 | 2005-12-22 | レジスト保護膜形成用材料およびこれを用いたレジストパターン形成方法 |
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US (1) | US8278025B2 (ja) |
EP (1) | EP1840655A4 (ja) |
JP (1) | JP4322205B2 (ja) |
KR (1) | KR100877217B1 (ja) |
CN (1) | CN101088047A (ja) |
TW (1) | TW200641542A (ja) |
WO (1) | WO2006070695A1 (ja) |
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US8034534B2 (en) * | 2006-08-14 | 2011-10-11 | E.I. Du Pont De Nemours And Company | Fluorinated polymers for use in immersion lithography |
Also Published As
Publication number | Publication date |
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KR20070086984A (ko) | 2007-08-27 |
US20080299503A1 (en) | 2008-12-04 |
JP2006184574A (ja) | 2006-07-13 |
EP1840655A1 (en) | 2007-10-03 |
JP4322205B2 (ja) | 2009-08-26 |
EP1840655A4 (en) | 2009-08-12 |
CN101088047A (zh) | 2007-12-12 |
KR100877217B1 (ko) | 2009-01-07 |
TW200641542A (en) | 2006-12-01 |
US8278025B2 (en) | 2012-10-02 |
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