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WO2017006625A1 - Composition pour former un film protecteur, procédé de fabrication du film protecteur et stratifié - Google Patents

Composition pour former un film protecteur, procédé de fabrication du film protecteur et stratifié Download PDF

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Publication number
WO2017006625A1
WO2017006625A1 PCT/JP2016/064553 JP2016064553W WO2017006625A1 WO 2017006625 A1 WO2017006625 A1 WO 2017006625A1 JP 2016064553 W JP2016064553 W JP 2016064553W WO 2017006625 A1 WO2017006625 A1 WO 2017006625A1
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Prior art keywords
protective film
resin
composition
group
forming
Prior art date
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Ceased
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PCT/JP2016/064553
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English (en)
Japanese (ja)
Inventor
雅史 小島
康智 米久田
渋谷　明規
長生 山本
敬充 冨賀
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Fujifilm Corp
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Fujifilm Corp
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Priority to JP2017527110A priority Critical patent/JPWO2017006625A1/ja
Publication of WO2017006625A1 publication Critical patent/WO2017006625A1/fr
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives

Definitions

  • the present invention relates to a protective film-forming composition, a protective film manufacturing method, and a laminate. More specifically, a composition used for embedding fine recesses (eg, trenches) such as a substrate used in an electronic device such as a semiconductor device, a method for producing a protective film using the composition, and It relates to the obtained laminate.
  • a composition used for embedding fine recesses eg, trenches
  • a substrate used in an electronic device such as a semiconductor device
  • a method for producing a protective film using the composition relates to the obtained laminate.
  • Patent Document 1 discloses a resist underlayer film forming composition containing a resin, a liquid additive, and a solvent, and discloses that the composition can be applied to the above-described embedding use.
  • a substrate having a recess or a resist pattern may be covered with a protective film for the purpose of preventing damage in an ion implantation process or the like.
  • the protective film is firmly embedded in a recess such as a hole or a trench or a gap between resist pattern patterns.
  • the formed protective film is also required to have a flat surface. If the flatness of the surface of the protective film is not sufficient, the processing accuracy of the finally obtained substrate will be adversely affected.
  • the present inventors have found that a desired effect can be obtained by using two kinds of resins, and have reached the present invention. That is, the present inventor has found that the above problem can be solved by the following configuration.
  • a protective film forming composition used for embedding a stepped substrate A resin A having a glass transition temperature higher than 25 ° C .; A resin B having a glass transition temperature of 25 ° C. or lower and a weight average molecular weight of 1500 or more; A protective film-forming composition comprising a solvent.
  • Resin A contains a resin having at least one repeating unit selected from the group consisting of repeating units represented by the following general formulas (D-1) to (D-3): A composition for forming a protective film according to 1.
  • the resin A according to (2), wherein the resin A contains at least a repeating unit represented by the following general formula (D-1) and a repeating unit represented by the following general formula (D-4) A composition for forming a protective film.
  • the composition for protective film formation which is excellent in the embedding property to a level
  • FIG. 6 is a schematic cross-sectional view for explaining a mode in which voids and voids are generated in the embedded portion and the flatness of the protective film is poor.
  • composition for forming a protective film of the present invention (hereinafter also simply referred to as “composition”) will be described below.
  • the notation that does not indicate substitution and non-substitution includes not only a substituent but also a substituent.
  • the “alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • the characteristic point of the composition for forming a protective film of the present invention is that two types of resins having different properties are used.
  • the present inventors have studied the reason why a desired effect cannot be obtained in the conventional technique described in Patent Document 1, and have found the following. As shown in FIG. 4, when the stepped substrate 10 having the trench 12 that is a recess is embedded using the technique described in Patent Document 1, the protective film 16 is embedded in the trench 12, but the void 20 and the void 22 are formed. And the flatness of the protective film 16 in the trench 12 portion is impaired.
  • the liquid additive used in Patent Document 1 has a low molecular weight, so that the liquid additive volatilizes during baking during the formation of the protective film, resulting in voids and voids, and further film shrinkage occurs. It is presumed that the flatness is deteriorated. Therefore, the present inventors have solved the above problem by using a resin A having a high glass transition temperature and a resin B having a low glass transition temperature and a relatively large molecular weight. Although the detailed mechanism is unknown, it is expected as follows. Resin B improves embedding in a recess or a gap when a protective film is formed.
  • the resin B itself has a relatively large molecular weight, unlike the liquid additive of Patent Document 1, the resin B is less likely to volatilize and easily remains in the protective film, thereby suppressing generation of voids and voids and film shrinkage. Moreover, the followability to the recessed part on the surface of the protective film is lowered by the resin A, and the flatness of the protective film is improved.
  • the composition (embedding composition) of the present invention comprises a resin A having a glass transition temperature higher than 25 ° C., a resin B having a glass transition temperature of 25 ° C. or lower and a weight average molecular weight of 1500 or higher, and a solvent C. And containing.
  • a resin A having a glass transition temperature higher than 25 ° C. a resin B having a glass transition temperature of 25 ° C. or lower and a weight average molecular weight of 1500 or higher
  • a solvent C containing
  • Resin A is a resin having a glass transition temperature higher than 25 ° C.
  • the glass transition temperature of the resin A is higher than 25 ° C., and in particular, at least one of embedding property and flatness of the protective film is more excellent (hereinafter, also simply referred to as “the effect of the present invention is more excellent”). 50 ° C. or higher is preferable, and 70 ° C. or higher is more preferable.
  • the upper limit is not particularly limited, but is preferably 200 ° C. or less from the viewpoint of handleability, and more preferably 165 ° C. or less from the viewpoint of more excellent effects of the present invention.
  • the measurement method of the glass transition temperature of Resin A is JIS K 7121 (1987) (Method for measuring the transition temperature of plastic) using a differential scanning calorimeter [product name “Q1000” manufactured by TA Instruments]. Determined according to a similar method. Specifically, a 3 mg powder sample is heated twice (heating rate: 10 ° C./min) in a nitrogen atmosphere (gas flow rate: 80 ml / min) and measured twice, and the second data is adopted.
  • the type of the resin A is not particularly limited as long as it satisfies the above glass transition temperature requirements.
  • polystyrene resin, poly (meth) acrylic resin, polyester resin, polyether resin, polyvinyl alcohol resin, novolac Resin, polysiloxane resin and the like it is preferable that it is at least 1 type of resin selected from the group which consists of a polystyrene-type resin, a novolak-type resin, and a poly (meth) acrylic-type resin at the point which the effect of this invention is more excellent.
  • the poly (meth) acrylic resin is a concept including a polyacrylic resin and a polymethacrylic (methacrylic) resin.
  • the resin A is preferably a resin having a phenolic hydroxyl group.
  • the phenolic hydroxyl group is a group formed by substituting a hydrogen atom of an aromatic ring with a hydroxy group.
  • This aromatic ring is a monocyclic or polycyclic aromatic ring, and examples thereof include a benzene ring and a naphthalene ring.
  • a preferred embodiment of the resin A is a resin having at least one repeating unit selected from the group consisting of the following general formulas (D-1) to (D-3) in that the effect of the present invention is more excellent. It is done.
  • R 1 represents a hydrogen atom or a monovalent organic group.
  • the monovalent organic group represented by R 1 it is preferable to use those having 1 to 30 carbon atoms (preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms). More preferably, it is an alkyl group, an aryl group, or a heteroaryl group.
  • the alkyl group may be linear or branched.
  • a hetero atom contained in a heteroaryl group a sulfur atom (S), an oxygen atom (O), a nitrogen atom (N) etc. are mentioned, for example.
  • the organic group may be unsubstituted or may have a substituent.
  • the organic group has a substituent
  • substituents include a halogen atom, an alkyl group (including a cycloalkyl group), an alkenyl group (including a cycloalkenyl group and a bicycloalkenyl group), an alkynyl group, an aryl Group, heterocyclic group, cyano group, hydroxy group, nitro group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy, Amino group (including anilino group), acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino group, mercapto group, alkylthio group,
  • L 1 represents a single bond or a divalent linking group.
  • the divalent linking group represented by L 1 include an alkylene group, a cycloalkylene group, —N (R d1 ) —, —O—, —CO—, —CO 2 —, —S—, —SO 3 —. , —SO 2 N (R d1 ) —, or a divalent group obtained by combining these.
  • R d1 represents a hydrogen atom or an alkyl group.
  • L 1 is preferably a single bond from the viewpoint that the effects of the present invention are more excellent.
  • Ar represents an aromatic ring.
  • the aromatic ring represented by Ar include groups such as a benzene ring, a condensed polycyclic aromatic ring having 2 to 5 rings (for example, a naphthalene ring, an anthracene ring, etc.), a biphenyl ring, a terphenyl ring, and a quaterphenyl ring.
  • a benzene ring or a condensed polycyclic aromatic ring having 2 to 5 rings is preferable from the viewpoint of achieving both heat resistance when forming a protective film and high solubility in the composition for forming a protective film.
  • a ring or a naphthalene ring is more preferable, and a benzene ring is more preferable.
  • the aromatic ring representing Ar may have a substituent other than — (OH) n represented by the general formula (D-1). Examples of such a substituent include the substituents described in the organic group described above. Can be mentioned.
  • n represents an integer of 1 to 5.
  • n represents an integer of 1 to 5, and is preferably an integer of 1 to 3 from the viewpoint of solubility in an organic solvent (a solvent described later) that may be contained in the protective film-forming composition. 1 is more preferable.
  • the repeating unit represented by the general formula (D-1) is preferably a repeating unit represented by the following general formula (D-1a).
  • R 1 represents a hydrogen atom or a monovalent organic group.
  • L 1 represents a single bond or a divalent linking group.
  • n1 represents an integer of 1 to 5. Definitions and preferable ranges of R 1, L 1 and n1 in Formula (D-1a) are each and R 1, L 1 and n in the above-mentioned general formula (D-1) synonymous.
  • R 2 to R 4 each independently represents a hydrogen atom or a monovalent organic group.
  • the definition and preferred range of the monovalent organic group are as described above.
  • Ar represents an aromatic ring.
  • the definition and preferred range of the aromatic ring are as described above.
  • m represents an integer of 0 to 3. Among these, 0 to 2 is preferable and 0 is more preferable in that the effect of the present invention is more excellent.
  • l represents an integer of 1 to 4. Among these, 1 to 3 is preferable and 1 is more preferable in that the effect of the present invention is more excellent.
  • the repeating unit represented by the general formula (D-2) is preferably a repeating unit represented by the following general formula (D-2a).
  • R 5 represents a hydrogen atom or a monovalent organic group.
  • the definition and preferred range of the monovalent organic group are as described above.
  • L 2 represents a divalent linking group.
  • the definition of a bivalent coupling group is as the above-mentioned. Among these, —CO— is preferable in that the effect of the present invention is more excellent.
  • Z represents an oxygen atom, a sulfur atom, or a nitrogen atom. Especially, an oxygen atom is preferable at the point which the effect of this invention is more excellent.
  • R 6 represents a hydrogen atom or a monovalent organic group. Especially, a monovalent organic group is preferable and an alkyl group is more preferable at the point which the effect of this invention is more excellent.
  • the total content of repeating units selected from the group consisting of repeating units represented by the general formulas (D-1) to (D-3) in the resin A is not particularly limited, but the effects of the present invention are more excellent. Therefore, the content is preferably 1 to 100 mol%, more preferably 50 to 100 mol%, and still more preferably 75 to 100 mol% with respect to all repeating units in the resin A.
  • R 7 represents a hydrogen atom or a monovalent organic group.
  • the definition and preferred range of the monovalent organic group are as described above.
  • R 8 represents an alkyl group. Examples of the alkyl group include an alkyl group having 1 to 10 carbon atoms, and preferably a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group. Group, isopropyl group, sec-butyl group, isobutyl group, 2-ethylhexyl group and the like.
  • This alkyl group may have a substituent, and examples of the substituent include the substituent that the above-described monovalent organic group may have, and for example, a hydroxy group is preferable.
  • L 3 represents a single bond or a divalent linking group.
  • the definition of a bivalent coupling group is as the above-mentioned.
  • Ar represents an aromatic ring. The definition and preferred range of the aromatic ring are as described above.
  • n2 represents an integer of 1 to 5.
  • n3 represents an integer of 0 to 4 that satisfies n2 + n3 ⁇ 5.
  • n2 is preferably an integer of 1 to 4, more preferably 1 or 2.
  • n3 is preferably an integer of 0 to 4, more preferably an integer of 0 to 2.
  • the repeating unit represented by the general formula (D-4) is preferably a repeating unit represented by the following general formula (D-4a).
  • R 7 in (D-4a) in, R 8, L 3, n2 and n3 have the same meanings as R 7, R 8, L 3, n2 and n3 in general formula (D-4) .
  • the repeating unit represented by the general formula (D-1) and the repeating unit represented by the general formula (D-4) are contained in the resin A, the repeating unit represented by the general formula (D-1)
  • the content is preferably from 1 to 99 mol%, more preferably from 40 to 99 mol%, more preferably from 70 to 99 mol%, based on all repeating units of the resin A, from the viewpoint that the effects of the present invention are more excellent. More preferably, it is mol%.
  • the content of the repeating unit represented by the general formula (D-4) is preferably 1 to 99 mol% with respect to all the repeating units of the resin A in that the effect of the present invention is more excellent.
  • the amount is more preferably 1 to 60 mol%, further preferably 1 to 30 mol%.
  • the lower limit of the weight average molecular weight (Mw) of the resin A is preferably 1000 or more, more preferably 2000 or more, from the viewpoint that the effect of the present invention is more excellent.
  • As an upper limit 30000 or less is preferable, 20000 or less is more preferable, 8000 or less is further more preferable, and 6000 or less is especially preferable.
  • the resin A is naturally low in impurities such as metals, and has a residual monomer (with a molecular weight of less than 500) and an oligomer component (with a molecular weight of 500 to less than 1000) of 0 to 10% by mass. It is preferably 0 to 5% by mass, more preferably 0 to 1% by mass.
  • the molecular weight distribution (Mw / Mn, also referred to as dispersity) is preferably 1 to 5, more preferably 1 to 3, and still more preferably 1 to 2.
  • the weight average molecular weight (Mw) and dispersity (Mw / Mn) of each component in the present invention are 4 HLC-8320GPC (GPC (Gel permeation chromatography) columns manufactured by Tosoh): 4 Multipore Hxl-M manufactured by Tosoh ), Flow rate: 1.0 mL / min, elution solvent: tetrahydrofuran, column temperature: measured by a gel permeation chromatograph (detector: differential refractometer) using monodisperse polystyrene as a standard under the analysis conditions of 40 ° C.
  • the weight average molecular weight (Mw) and dispersity (Mw / Mn) of each component in the present invention are 4 HLC-8320GPC (GPC (Gel permeation chromat
  • the resin A various commercially available products can be used, or they can be synthesized according to a conventional method (for example, radical polymerization).
  • a conventional method for example, radical polymerization
  • a general synthesis method a batch polymerization method in which a monomer species and an initiator are dissolved in a solvent and polymerization is performed by heating, and a solution of the monomer species and the initiator is dropped into the heated solvent over 1 to 10 hours.
  • the dropping polymerization method is added, and the dropping polymerization method is preferable.
  • the content of the resin A in the composition is not particularly limited, but is preferably from 10 to 95% by mass, preferably from 30 to 90% by mass based on the total solid content of the composition for forming a protective film, from the viewpoint that the effects of the present invention are more excellent. More preferably, it is more preferably 50 to 90% by weight.
  • the composition of this invention may contain only 1 type as the resin A, and may contain 2 or more types.
  • Resin B is a resin having a glass transition temperature of 25 ° C. or lower and a weight average molecular weight of 1500 or higher.
  • the glass transition temperature of the resin B is 25 ° C. or lower, and among them, 0 ° C. or lower is preferable and ⁇ 25 ° C. or lower is more preferable in terms of more excellent effects of the present invention.
  • the lower limit is not particularly limited, but is preferably ⁇ 80 ° C. or higher from the viewpoint of handleability.
  • the measuring method of the glass transition temperature is the same as the measuring method of the glass transition temperature of the resin A described above.
  • the weight average molecular weight of the resin B is 1500 or more, and 2000 or more is preferable in that the effect of the present invention is more excellent.
  • the upper limit is not particularly limited, but is preferably 30000 or less from the viewpoint of handleability, more preferably 10000 or less, and even more preferably 6000 or less in terms of more excellent effects of the present invention.
  • the method for measuring the weight average molecular weight is the same as the method for measuring the weight average molecular weight of the resin A described above.
  • the type of resin B is not particularly limited as long as it satisfies the above glass transition temperature and weight average molecular weight requirements.
  • resin B is not particularly limited as long as it satisfies the above glass transition temperature and weight average molecular weight requirements.
  • polystyrene resin poly (meth) acrylic resin, polyester resin, polyether resin, polyvinyl alcohol Resin, novolac resin, polysiloxane resin and the like.
  • the thermal decomposition temperature of the resin B is not particularly limited, but is preferably 250 ° C. or higher and more preferably 300 ° C. or higher in terms of more excellent effects of the present invention.
  • the upper limit is not particularly limited, but is often 450 ° C. or lower.
  • the said thermal decomposition temperature intends 10% thermal decomposition temperature (what is called T10 % ) by the thermal mass reduction
  • the thermal decomposition temperature of the resin B can be measured as follows using a differential type differential thermal balance (TG-DTA: TG8120 manufactured by Rigaku Corporation). The sample mass is 5 mg, and then the mass decrease is measured while heating from room temperature to 450 ° C.
  • a preferred embodiment of the resin B includes a repeating unit represented by the general formula (B-1) in that the effect of the present invention is more excellent.
  • R 10 represents a hydrogen atom or a monovalent organic group.
  • the definition and preferred range of the monovalent organic group are as described above.
  • R 11 represents an alkyl group.
  • the alkyl group may be linear, branched, or cyclic.
  • the number of carbon atoms contained in the alkyl group is preferably 1 to 12, and more preferably 1 to 8.
  • the content of the repeating unit represented by formula (B-1) in the resin B is 1 to 100 mol% with respect to all the repeating units of the resin B in that the effect of the present invention is more excellent. Is more preferable, 50 to 100 mol% is more preferable, and 75 to 100 mol% is still more preferable.
  • the resin B various commercially available products can be used, or they can be synthesized according to a conventional method (for example, radical polymerization).
  • examples of commercially available products include Alfon manufactured by Toagosei Co., Ltd. and Actflow manufactured by Soken Chemical Co., Ltd.
  • the content of the resin B in the composition is not particularly limited, but it is preferably 5 to 90% by mass with respect to the total solid content of the composition for forming a protective film in terms of more excellent effects of the present invention.
  • the content is more preferably 10 to 70% by mass, and further preferably 10 to 50% by mass.
  • the composition of this invention may contain only 1 type as resin B, and may contain 2 or more types.
  • the mixing mass ratio of the resin A and the resin B described above is not particularly limited, but the mass ratio of the resin A and the resin B (the mass of the resin A / the mass of the resin B) is 9 in that the effect of the present invention is more excellent. / 1 to 5/5 is preferable, and 7/3 to 5/5 is more preferable.
  • the composition includes a solvent.
  • the type of solvent used is not particularly limited, but a solvent that dissolves and disperses the above-described resin A and resin B is preferable.
  • Such a solvent is not particularly limited, and for example, it can be appropriately selected from those listed below.
  • Ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene Ethylene glycol monoalkyl ether acetates such as glycol mono-n-propyl ether acetate and ethylene glycol mono-n-butyl ether acetate; diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol di-n-propyl ether, diethylene glycol di-n-butyl ether, etc.
  • Diethylene glycol dialki Ethers Diethylene glycol dialki Ethers; triethylene glycol dialkyl ethers such as triethylene glycol dimethyl ether and triethylene glycol diethyl ether; propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, etc.
  • solvent C two or more kinds of solvents may be used in combination, and it is preferable to use two or more kinds of solvents having different boiling points from the viewpoint that the effect of the present invention is more excellent, and the boiling point is less than 180 ° C. It is more preferable to use a first solvent (hereinafter referred to as “solvent (C1)”) and a second solvent having a boiling point of 180 ° C. or higher (hereinafter referred to as “solvent (C2)”). preferable.
  • solvent (C1) a first solvent
  • solvent (C2) a second solvent having a boiling point of 180 ° C. or higher
  • the difference in boiling point between the solvent (C1) and the solvent (C2) is preferably 40 ° C. or higher, more preferably 50 ° C. or higher, and further preferably 60 ° C. or higher. Moreover, it is preferable that the difference of the boiling point of a solvent (C1) and a solvent (C2) is 100 degrees C or less, for example.
  • the boiling point means a boiling point under a pressure of 1 atm, that is, 1.013 ⁇ 10 5 N / m 2 .
  • the blending ratio of the solvent (C1) and the solvent (C2) in the composition of the present invention is represented by the following formula (1): "Is preferably 1 or more, more preferably 1 to 20, and still more preferably 1 to 10. Mass of solvent (C1) / mass of solvent (C2) (1)
  • the “mass of the solvent (C1)” in the formula (1) and / or “solvent ( The “mass of C2)” means the total mass.
  • the content of the solvent C in the composition is not particularly limited, but the solid content concentration of the composition for forming a protective film is preferably 0.1 to 30% by mass, and more preferably 1 to 20% by mass. . By making the solid content concentration of the composition for forming a protective film within the above range, the coating property is improved.
  • Each component (resin A, resin B, solvent C) contained in the composition of the present invention preferably does not contain impurities such as metals.
  • the content of impurities contained in these materials is preferably 100 ppt or less, more preferably 30 ppt or less, further preferably 10 ppt or less, and particularly preferably (not more than the detection limit of the measuring device).
  • Examples of methods for removing impurities such as metals include filtration using a filter.
  • the filter pore diameter is preferably 10 nm or less, more preferably 5 nm or less, and further preferably 3 nm or less.
  • a filter made of polytetrafluoroethylene, polyethylene, or nylon is preferable.
  • a filter that has been previously washed with an organic solvent may be used.
  • a plurality of types of filters may be connected in series or in parallel. When using multiple types of filters, filters with different pore diameters and / or materials may be used in combination.
  • various materials may be filtered a plurality of times, and the step of filtering a plurality of times may be a circulating filtration step.
  • impurities may be removed by an adsorbent, or a combination of filter filtration and adsorbent may be used.
  • adsorbent known adsorbents can be used.
  • inorganic adsorbents such as silica gel and zeolite, and organic adsorbents such as activated carbon can be used.
  • a method for reducing impurities such as metals there can be mentioned a method of performing distillation under a condition in which contamination is suppressed as much as possible by lining the inside of the apparatus with Teflon (registered trademark).
  • Teflon registered trademark
  • the preferable conditions for filter filtration performed on the raw materials constituting the various materials are the same as those described above.
  • composition may contain a surfactant, an acid generator, a crosslinking agent, a thermosetting polymer, a radiation absorber, and the like as necessary.
  • a surfactant an acid generator
  • a crosslinking agent a crosslinking agent
  • a thermosetting polymer a thermosetting polymer
  • a radiation absorber a radiation absorber
  • the composition for forming a protective film of the present invention preferably further contains a surfactant for the purpose of improving coating properties.
  • the surfactant is not particularly limited.
  • fluorine and / or silicon surfactant fluorine surfactant, silicon surfactant, surfactant having both fluorine atom and silicon atom is used. it can.
  • fluorine-based and / or silicon-based surfactant examples include surfactants described in [0276] of US2008 / 0248425A.
  • F-top EF301, EF303 (manufactured by Shin-Akita Kasei Co., Ltd.), Florard FC430, 431 4430 (manufactured by Sumitomo 3M Co., Ltd.), Megafac F171, F173, F176, F189, F113, F110, F177, F120, R08 (manufactured by DIC Corporation), Surflon S-382, SC101, 102, 103, 104 105, 106, KH-20 (manufactured by Asahi Glass Co., Ltd.), Troisol S-366 (manufactured by Troy Chemical Co., Ltd.), GF-300, GF-150 (manufactured by Toagosei Chemical Co., Ltd.), Surflon S-393 (Manufactured by Seimi Chemical Co
  • Surfactants were derived from fluoroaliphatic compounds produced by the telomerization method (also referred to as the telomer method) or the oligomerization method (also referred to as the oligomer method) in addition to the known ones as described above.
  • a surfactant using a polymer having a fluoroaliphatic group can be used.
  • the fluoroaliphatic compound can be synthesized by the method described in JP-A-2002-90991.
  • Requirement 1 The surface tension of a propylene glycol monomethyl ether solution in which 0.1% by mass of a surfactant is dissolved is 25 mN / m or more.
  • the requirement 1 is intended to prepare a solution X in which 0.1% by mass of a surfactant is dissolved in propylene glycol monomethyl ether, and the surface tension of the solution X is 25 mN / m or more.
  • a preferable range of the surface tension of the solution X is preferably 26 mN / m or more, and more preferably 27 mN / m or more.
  • the upper limit is not particularly limited, but is often 30 mN / m or less.
  • the surface tension is determined by a plate method using CBVP-A3 manufactured by Kyowa Interface Science Co., Ltd.
  • the content is preferably 0.001 to 50% by mass and preferably 0.01 to 50% by mass with respect to the total solid content of the protective film-forming composition. More preferably, it is 0.1 to 50% by mass.
  • coating property of the composition for protective film formation improves more because content of surfactant exists in the said range.
  • the acid generator is a component that generates an acid by exposure or heating. By containing the acid generator, it is possible to eliminate the crosslinking reaction inhibition.
  • Crosslinking reaction inhibition refers to, for example, diffusion of a substance (base such as OH ⁇ , CH 3 ⁇ , NH 2 —, etc.) generated from a substrate (particularly a low dielectric film) into the protective film, thereby Intended to inactivate and inhibit cross-linking reactions. That is, when the acid generator in the protective film to be formed reacts with the inhibitory substance, it is possible to prevent the inhibitory substance from diffusing into the protective film.
  • acid generators that generate an acid upon exposure
  • photoacid generators diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodonium pyrenesulfonate, diphenyliodonium n-dodecylbenzenesulfonate, diphenyliodonium 10-camphorsulfonate, diphenyliodonium naphthalenesulfonate, Bis (4-t-butylphenyl) iodonium trifluoromethanesulfonate, bis (4-t-butylphenyl) iodonium nonafluoro-n-butanesulf
  • photoacid generators may be used alone or in combination of two or more.
  • the acid generator that generates an acid upon heating include 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl, and the like. Tosylate, alkyl sulfonates and the like can be mentioned.
  • thermal acid generators may be used alone or in combination of two or more.
  • a photo-acid generator and a thermal acid generator can also be used together as an acid generator.
  • the content is preferably 100 parts by mass or less, more preferably 0.1 to 30 parts by mass, and more preferably 0.1 to 30 parts by mass with respect to 100 parts by mass in total of the resin A and the resin B described above. 10 parts by mass is more preferable.
  • the composition for forming a protective film of the present invention can be cured at a lower temperature to form a protective film.
  • a crosslinking agent polynuclear phenols and various other curing agents can be used.
  • polynuclear phenols examples include dinuclear phenols such as 4,4′-biphenyldiol, 4,4′-methylene bisphenol, 4,4′-ethylidene bisphenol, and bisphenol A; 4,4 ′, 4 ′′- Trinuclear phenols such as methylidenetrisphenol, 4,4 ′-[1- [4- [1- (4-hydroxyphenyl) -1-methylethyl] phenyl] ethylidene] bisphenol; polyphenols such as novolak Can be mentioned.
  • dinuclear phenols such as 4,4′-biphenyldiol, 4,4′-methylene bisphenol, 4,4′-ethylidene bisphenol, and bisphenol A
  • 4,4 ′, 4 ′′- Trinuclear phenols such as methylidenetrisphenol, 4,4 ′-[1- [4- [1- (4-hydroxyphenyl) -1-methyleth
  • 4,4 ′-[1- [4- [1- (4-hydroxyphenyl) -1-methylethyl] phenyl] ethylidene] bisphenol and novolak are preferable.
  • these polynuclear phenols may be used independently and may be used in mixture of 2 or more types.
  • the curing agent include diisocyanates, epoxy compounds, melamine curing agents, benzoguanamine curing agents, glycoluril curing agents, and the like.
  • melamine curing agents and glycoluril curing agents are preferable, and 1,3,4,6-tetrakis (methoxymethyl) glycoluril is more preferable.
  • curing agents may be used independently and may mix and use 2 or more types.
  • curing agent can also be used together as a crosslinking agent.
  • the content is preferably 100 parts by mass or less, more preferably 1 to 20 parts by mass, and further preferably 1 to 10 parts by mass with respect to 100 parts by mass in total of the resin A and the resin B described above. preferable.
  • thermosetting polymer Various thermosetting polymers can be used as the thermosetting polymer.
  • a thermosetting polymer is a component which has the effect
  • thermosetting polymers include acrylic polymers (thermosetting acrylic polymers), phenol polymers, urea polymers, melamine polymers, amino polymers, aromatics, and the like.
  • Radiation absorber examples include oil-soluble dyes, disperse dyes, basic dyes, methine dyes, pyrazole dyes, imidazole dyes, hydroxyazo dyes, and the like; bixin derivatives, norbixine, stilbene, 4,4 Examples thereof include fluorescent brighteners such as' -diaminostilbene derivatives, coumarin derivatives, pyrazoline derivatives, and ultraviolet absorbers.
  • these radiation absorbers may be used independently and may mix and use 2 or more types.
  • the content in the case of containing the radiation absorber is preferably 50 parts by mass or less, more preferably 1 to 10 parts by mass with respect to 100 parts by mass in total of the resin A and the resin B described above.
  • composition for forming a protective film of the present invention may contain other components such as a storage stabilizer, an antifoaming agent, and an adhesion aid as necessary in addition to the above components.
  • the preparation method (manufacturing method) of the composition for forming a protective film of the present invention is not particularly limited, and a known method can be adopted.
  • the protective film-forming composition of the present invention can be obtained by adding a predetermined amount of a resin (and further, if necessary, each component described above) to a solvent and appropriately performing a stirring treatment. Moreover, you may process filtration etc. at a desired timing as needed.
  • a stepped substrate means a substrate having a portion embedded with a protective film forming composition, and includes, for example, a substrate having a recess, a resist pattern having a gap between patterns, and the like.
  • the resist pattern may be disposed on a predetermined substrate, and a laminate including the substrate and the resist pattern disposed on the substrate may be used as the stepped substrate.
  • FIG. 1 is a schematic view showing an example of a method for producing a protective film of the present invention step by step.
  • FIG. 1 is a schematic view showing an example of a method for producing a protective film of the present invention step by step.
  • the protective film-forming composition of the present invention is used for embedding gaps between substrates or resist patterns.
  • FIG. 1 below, a substrate having recesses was used. The case will be described in detail.
  • a coating process is a process of apply
  • a stepped substrate 10 having a trench 12 having a predetermined opening width and depth is prepared.
  • the protective film-forming composition is applied onto the stepped substrate 10 to produce a coating film 14. By this step, the protective film forming composition flows into the trench 12 to fill the trench 12.
  • a known application method can be appropriately used.
  • a coating method include a spin coating method, a dip coating method, a roller blade method, and a spray method, and the spin coating method is preferable from the viewpoint of productivity.
  • the coating film thickness (indicated as A in FIG. 1B) on the surface of the stepped substrate 10 is preferably 10 to 1000 nm. Preferably, it may be 30 to 500 nm.
  • the manufacturing method of the stepped substrate 10 having the trench 12 is not particularly limited, and a known method can be used. For example, a method in which a photoresist process and an etching process are combined can be used. More specifically, a method of depositing an insulating film made of a mask nitride film / pad oxide film on a substrate and then etching it into a pattern can be used.
  • the stepped substrate may have, for example, a bottomed hole structure or a trench structure.
  • the aspect ratio represented by height / diameter is 0.2 to 50, preferably 0.5 to 20, and more preferably 1 to 10.
  • the bottomed trench structure for example, the aspect ratio represented by height / groove width is 0.2 to 50, preferably 0.5 to 20, and more preferably 1 to 10.
  • the measuring method of the opening width and depth of the hole structure and the trench structure can be measured by a known method.
  • the cross section of the stepped substrate can be obtained by observing with a SEM (scanning electron microscope).
  • the stepped substrate 10 may have a plurality of holes and trenches having the same opening size (groove width and diameter), depth and aspect ratio on the surface thereof, and different opening sizes (groove width and diameter) and depth.
  • a plurality of types of holes and trenches having a thickness / aspect ratio may be provided.
  • the material constituting the stepped substrate 10 is not particularly limited, and silicon, silicon carbide, metal (gold, silver, copper, nickel, aluminum, etc.), metal nitride (silicon nitride, titanium nitride, tantalum nitride, tungsten nitride, etc.) Glass (quartz glass, borate glass, soda glass, etc.), resin (polyethylene terephthalate, polyimide, etc.), insulating film (silicon oxide, titanium oxide, zirconium oxide, hafnium oxide, etc.).
  • the manufacturing method of the protective film of this invention may have a solvent removal process of giving the heat processing etc. to the apply
  • Solvent removal is carried out by placing the coated film on the condition of preferably 60 to 500 ° C., more preferably 100 to 450 ° C., preferably 1 to 10 minutes, more preferably 1 to 5 minutes.
  • the solvent removal may be performed twice or more under different conditions.
  • the curing step is a step of forming the protective film 16 by curing the coating film 14 (see FIG. 1C). Thereby, the laminated body 18 which consists of the level
  • the protective film 16 includes a trench embedded portion 16 a formed by embedding the coating film 14 in the trench 12.
  • the curing step may also serve as the solvent removal step described above.
  • the coating method of the said coating film 14 is not limited to this, The method of performing at least one process of a light irradiation process and a heat processing with respect to the coating film 14 can be used.
  • the apparatus used for the light irradiation treatment or the heat treatment may be a known light irradiation apparatus or heating apparatus, and is not particularly limited.
  • As the light used for the light irradiation treatment for example, when an acid generator is contained in the composition for forming a protective film, depending on the type of the acid generator, visible light, ultraviolet rays, far ultraviolet rays, X-rays are used. , Electron beam, ⁇ -ray, molecular beam, ion beam, etc. may be appropriately selected.
  • the heating temperature in the heat treatment is not particularly limited, but is preferably 90 ° C to 650 ° C, more preferably 90 ° C to 450 ° C, and further preferably 90 ° C to 350 ° C.
  • the time for the heat treatment is not particularly limited, but is preferably 1 second to 10 minutes, and more preferably 10 seconds to 5 minutes.
  • the method for producing a protective film of the present invention uses the protective film-forming composition described above. Therefore, even when a stepped substrate having a nanometer level opening size (for example, 5 to 1000 nm) on the surface and having a deep hole trench (the above-described aspect ratio is 0.2 to 50) is used for protection. A protective film excellent in embedding property of the film forming composition and excellent in flatness can be obtained.
  • FIG. 1 details the case where a substrate having a recess is used
  • the composition of the present invention may be used to fill a gap between patterns of a resist pattern.
  • a photosensitive resin used in manufacturing the resist pattern a normal photoresist used for processing a semiconductor substrate can be applied.
  • the type of resist is not particularly limited and can be selected according to the purpose. Examples of resist types include acrylic resins, silicone resins, fluorine resins, polyimide resins, polyolefin resins, alicyclic olefin resins, and epoxy resins.
  • the type of resist is not limited to these, but an acrylic resin is preferable.
  • a method of forming a pattern on the substrate with the photosensitive resin is not particularly limited, and a method that is usually applied to processing of a semiconductor substrate can be used.
  • a method that is usually applied to processing of a semiconductor substrate can be used.
  • the photosensitive resin is applied onto a substrate with a spin coater or the like, and the reticle is exposed with a stepper and exposed to cure the photosensitive resin into a desired pattern. Thereafter, uncured portions of the photosensitive resin are removed by washing or ashing to form a resist pattern having a desired pattern gap (hole, groove).
  • a patterning technique a liquid immersion system or a double patterning technique may be used in addition to a normal system.
  • KrF, ArF, EUV Extreme ultraviolet lithography
  • electron beam or X-ray can be applied.
  • EUV is preferable.
  • various materials for example, a protective film forming composition, a resist composition, an organic solvent, an additive, etc.
  • the content of impurities contained in these materials is preferably 1 ppm or less, more preferably 10 ppb or less, further preferably 100 ppt or less, particularly preferably 10 ppt or less, and substantially not contained (below the detection limit of the measuring device). Is most preferable.
  • Examples of the method for removing impurities such as metals from various materials include filtration using a filter.
  • the filter pore diameter is preferably 10 nm or less, more preferably 5 nm or less, and further preferably 3 nm or less.
  • a filter made of polytetrafluoroethylene, polyethylene, or nylon is preferable.
  • the filter may be a composite material obtained by combining these materials and ion exchange media.
  • a filter that has been washed in advance with an organic solvent may be used.
  • a plurality of types of filters may be connected in series or in parallel. When using multiple types of filters, filters with different pore diameters and / or materials may be used in combination.
  • various materials may be filtered a plurality of times, and the step of filtering a plurality of times may be a circulating filtration step.
  • an apparatus that selects a raw material having a low metal content as a raw material constituting each material, and performs filter filtration on the raw material constituting each material. Examples thereof include a method of performing distillation under conditions where contamination is suppressed as much as possible by lining the inside with Teflon. The preferable conditions for filter filtration performed on the raw materials constituting the various materials are the same as those described above.
  • composition for forming a protective film of the present invention will be described in detail using examples.
  • present invention is not limited to this.
  • Resin A-3> As resin A-3, TD-2090 manufactured by DIC Corporation was used.
  • composition for forming protective film ⁇ Preparation of composition for forming protective film>
  • Resin A, resin B, and surfactant in Table 1 were dissolved in solvent C in Table 1 so that each component in Table 1 had the ratio of Table 1, and this was dissolved in a pore size of 0.1 ⁇ m.
  • surface is a ratio (mass%) on the basis of the mass of each component with respect to the composition total mass.
  • 3.0 g of resin A-1 and 1.8 g of resin A-3 were mixed.
  • 2.0 g of resin B-1 and 1.2 g of resin B-4 were mixed.
  • Solvent C-1 propylene glycol monomethyl ether acetate (boiling point: 145 ° C.)
  • Solvent C-2 ethyl 3-ethoxypropionate (boiling point: 166 ° C.)
  • Solvent C-3 propylene glycol monomethyl ether (boiling point: 119 ° C.)
  • Solvent C-4 3-phenyl-1-propanol (boiling point: 229 ° C.)
  • Solvent C-5 Propylene glycol diacetate (boiling point: 190 ° C.)
  • Solvent C-6 Triethylene glycol dimethyl ether (boiling point: 216 ° C.)
  • Solvent C-7 Diethylene glycol monomethyl ethyl ether (boiling point: 202 ° C.)
  • Solvent C-8 ethylene glycol monophenyl ether (boiling point: 245 ° C.)
  • Solvent C-9 ethylene glycol mono
  • FIG. 2 is a schematic diagram for explaining a state in which a protective film is formed on the stepped substrate in this evaluation test. As shown in FIG.
  • the ISO pattern 32 indicates a region where a wiring groove is not formed
  • the LS pattern 34 indicates a region where a wiring groove is formed.
  • FIG. 3 is a schematic diagram for explaining the state of the void 20 and the gap 22 in the embedding test, and is an enlarged view of a part of the LS pattern 34 in FIG. 2 described above. Note that the sizes of the voids 20 and the voids 22 were quantified by observing the cross-sectional shape by SEM.
  • the region 36 is a region in which the void 20 and the void 22 do not exist and the embedding property is good.
  • the protective film-forming composition of the present invention exhibited excellent flatness and embedding properties.
  • comparison between Examples 1, 2, and 4 confirms that flatness and embedding are better when the glass transition temperature of resin B is 0 ° C. or lower (more preferably, ⁇ 25 ° C. or lower). It was done.
  • flatness and embedding property are more excellent when the weight average molecular weight of resin B is 10,000 or less.
  • Example 7 when the resin A contains at least the repeating unit represented by the general formula (D-1) and the repeating unit represented by the general formula (D-5), the flatness and embedding are achieved. It was confirmed that the property is superior. Moreover, it was confirmed from the comparison with Example 1 and 8 that flatness is more excellent when surfactant satisfies the requirement 1. Moreover, it was confirmed from the comparison with Example 1 and 11 that flatness is more excellent when using 2 or more types of solvents together.
  • Comparative Example 1 in which resin B is not used Comparative Example 2 in which resin A is not used, Comparative Example 3 in which a glass transition temperature is outside the predetermined range is used as Resin B, and the weight average molecular weight is outside the predetermined range It was confirmed that the desired effect could not be obtained in Comparative Examples 5 and 6 in which a compound having a weight average molecular weight outside the predetermined range was used. It was done.

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  • Wood Science & Technology (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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  • Application Of Or Painting With Fluid Materials (AREA)
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Abstract

L'invention concerne une composition qui permet de former un film protecteur et grâce à laquelle il est possible de former un film protecteur plat, présentant d'exceptionnelles propriétés d'enrobage sur un substrat à dents, un procédé de fabrication d'un film protecteur et un stratifié. La composition qui permet de former un film protecteur est utilisée dans l'enrobage d'un substrat à dents, la composition contenant une résine A ayant une température de transition vitreuse supérieure à 25 °C, une résine B ayant une température de transition vitreuse de 25 °C ou moins et un poids moléculaire moyen en poids de 1 500 ou plus, et un solvant.
PCT/JP2016/064553 2015-07-03 2016-05-17 Composition pour former un film protecteur, procédé de fabrication du film protecteur et stratifié Ceased WO2017006625A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001072916A (ja) * 1999-09-03 2001-03-21 Daicel Chem Ind Ltd 塗料組成物
JP2004331796A (ja) * 2003-05-07 2004-11-25 Sumitomo Osaka Cement Co Ltd 透明性被膜形成用塗料とそれを用いた透明性被膜及びそれを備えた透明基材並びに光学部材
JP2007084678A (ja) * 2005-09-21 2007-04-05 Kaneka Corp 塗料組成物、該組成物から得られる塗膜および該塗料組成物の製造方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001072916A (ja) * 1999-09-03 2001-03-21 Daicel Chem Ind Ltd 塗料組成物
JP2004331796A (ja) * 2003-05-07 2004-11-25 Sumitomo Osaka Cement Co Ltd 透明性被膜形成用塗料とそれを用いた透明性被膜及びそれを備えた透明基材並びに光学部材
JP2007084678A (ja) * 2005-09-21 2007-04-05 Kaneka Corp 塗料組成物、該組成物から得られる塗膜および該塗料組成物の製造方法

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