WO2018159665A1 - 異物除去用コーティング膜形成組成物 - Google Patents
異物除去用コーティング膜形成組成物 Download PDFInfo
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- WO2018159665A1 WO2018159665A1 PCT/JP2018/007471 JP2018007471W WO2018159665A1 WO 2018159665 A1 WO2018159665 A1 WO 2018159665A1 JP 2018007471 W JP2018007471 W JP 2018007471W WO 2018159665 A1 WO2018159665 A1 WO 2018159665A1
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- coating film
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02041—Cleaning
- H01L21/02079—Cleaning for reclaiming
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B08—CLEANING
- B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
- B08B7/00—Cleaning by methods not provided for in a single other subclass or a single group in this subclass
- B08B7/0014—Cleaning by methods not provided for in a single other subclass or a single group in this subclass by incorporation in a layer which is removed with the contaminants
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
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Definitions
- the present invention relates to a foreign matter removing coating film forming composition, a foreign matter removing method on a substrate, a substrate processing method, and a method for producing a laminated substrate, which can remove foreign matters formed on a substrate by a simple method.
- the present invention relates to a coating film forming composition for removing foreign matter, which is used in a semiconductor wafer temporary bonding step for manufacturing a semiconductor device.
- the semiconductor substrate (wafer) is affixed to the support substrate, especially in the so-called post-process, followed by back grinding (grinding), wiring creation process, etc., and then the support substrate is peeled off to obtain the desired semiconductor substrate
- the process of obtaining is being studied.
- the wafer is affixed with an adhesive (liquid composition containing polymer, back grind tape, dicing tape, etc.) resistant to subsequent processes (heating process, chemical treatment process), and then semiconductor
- substrate is performed, the contact bonding layer contained in an adhesive agent may remain as a foreign material (residue) on a board
- Patent Document 1 An antireflection film that can be dissolved in a developer for photoresist and developed and removed simultaneously with the photoresist is disclosed in an antireflection film used in semiconductor lithography (Patent Document 2).
- the problem to be solved by the present invention is to provide a simple method for removing foreign matters formed on a substrate in a semiconductor wafer temporary bonding step of semiconductor device manufacture, for example, and used in such a method. It is providing the coating film forming composition for a foreign material removal.
- the foreign matter removing coating film of the present invention is not limited to the temporary adhesion step as long as it is for removing foreign matter on the substrate.
- the coating for removing foreign substances is applied and baked in advance on the substrate bonding surface, and after forming a coating film, the bonding process, the wafer temporary bonding process, and the wafer peeling process are performed, and then with a developer. As a result of cleaning, it was found that the peeling residue after adhesion could be completely removed and the substrate was not damaged, and the present invention was completed.
- the present invention includes the following.
- a coating film forming composition for removing foreign matter which contains a polymer and a solvent and can form a coating film that dissolves in a developer.
- Composition Composition.
- the polymer is (a) a structural unit derived from a tetracarboxylic dianhydride compound, (b) a diamine compound having at least one carboxyl group, and (a) a tetracarboxylic dianhydride compound.
- composition according to [1] which is a polyamic acid having a structural unit derived from a diamine compound different from (b).
- a coating film for removing foreign matter which is a fired product of a coating film made of the composition according to any one of [1] to [4].
- step of forming the foreign matter includes a step of forming an adhesive layer on the coating film and a step of peeling the adhesive layer thereafter.
- step of forming the foreign matter includes a step of forming an adhesive layer on the coating film and a step of peeling the adhesive layer thereafter.
- the foreign matter is a peeling residue of the adhesive layer.
- the polymer is represented by the formula (1): (Wherein A 1 represents a tetravalent organic group and B 1 represents a trivalent organic group).
- the composition according to [12] further comprising a polyamic acid having a structure represented by: object.
- composition according to [12], wherein the polyamic acid is a polyamic acid produced from (a) a tetracarboxylic dianhydride compound and (b) a diamine compound having at least one carboxyl group.
- the polyamic acid is (a) a tetracarboxylic dianhydride compound, (b) a diamine compound having at least one carboxyl group, and (c) a polyamic acid produced from the diamine compound.
- [20] The composition according to [12] or [13], further comprising a compound having at least two epoxy groups.
- the method according to [22] further comprising a step of forming an adhesive layer after the step of forming the coating film and then peeling the adhesive layer.
- the foreign matter removing coating film of the present invention is formed on a substrate (processing substrate) in advance during a wafer temporary bonding process of a semiconductor wafer, and the substrate is bonded to a support substrate using an adhesive layer, and then in a wafer peeling process.
- the coating film for removing foreign matter of the present invention has resistance to a semiconductor substrate processing process (heat, chemicals) after temporary bonding, particularly when used in a temporary bonding process of a semiconductor wafer.
- the foreign matter removing coating film forming composition of the present invention contains a polymer soluble in a developer.
- the polymer is not particularly limited as long as it is soluble in a developer, but when used in a semiconductor wafer temporary bonding process, the polymer has resistance to a semiconductor substrate processing process (heat, chemicals) after temporary bonding. It is preferable that Specific examples include polyamic acid, vinyl polymer polymer reacted with olefin, polyamide, polyester, polycarbonate, polyurethane and the like, and preferably includes polyamic acid having a structure represented by formula (1) and a solvent. Furthermore, it is preferable to include a compound having at least two epoxy groups.
- the coating film forming composition for removing a foreign substance of the present invention comprises a polyamic acid having a structure represented by the formula (1) and a structure represented by the formula (2) and a solvent. Furthermore, it is preferable to include a compound having at least two epoxy groups. And the coating film forming composition for foreign substance removal of this invention contains a light absorbing compound, surfactant, etc. as arbitrary components.
- the ratio of the solid content in the coating film forming composition for removing a foreign substance of the present invention is not particularly limited as long as each component is uniformly dissolved, but is 0.5 to 50% by mass, for example, 1 ⁇ 30% by mass.
- the solid content is obtained by removing the solvent component from all the components of the foreign matter removing coating film forming composition.
- the foreign substance is a substance other than the target object attached on the substrate.
- it is an unnecessary substance in the semiconductor device manufacturing process. For example, particles adhering to the wafer, metal impurities, post-etching residues, adhesive stripping residues and the like can be mentioned.
- the foreign matter removing coating film of the present invention is formed by forming the coating film of the present invention before applying the adhesive in the step of bonding the wafers with an adhesive and then peeling the adhesive, and then bonding and peeling the wafer. It is particularly preferably used in order to remove foreign matter (adhesive residue) after performing the process.
- the dissolution of the foreign matter removing coating film of the present invention in the developer means that the coating film dissolves in the developer and does not exist from the substrate when immersed or washed in the developer described later.
- the dissolution referred to in the present invention means that the film formed on the substrate is removed by at least 90% or more from the initially formed film thickness (that is, the film thickness of the remaining film is initially set).
- the film thickness of the remaining film is 5% or less of the initial film thickness
- the film thickness of the remaining film is initially 1% or less of the film thickness
- most preferably 100% is removed (that is, the remaining film thickness is 0% of the initial film thickness (no remaining film)).
- the coating film forming composition for removing foreign matter of the present invention will be specifically described.
- the foreign matter removing coating film forming composition of the present invention has a polyamic acid having a structure represented by formula (1), or a structure represented by formula (1) and a structure represented by formula (2). It contains polyamic acid.
- a 1 represents a tetravalent organic group
- B 1 represents a trivalent organic group.
- a 1 include formulas (3) to (10) (wherein X is an alkyl group having 1 to 5 carbon atoms, a chlorine atom, a bromine atom, a fluorine atom, or an alkoxy group having 1 to 5 carbon atoms). Represents a hydroxyl group, a carboxyl group, a phenoxy group, a trifluoromethyl group or a nitro group, and m represents a number of 0, 1 or 2.
- Examples of B 1 include formulas (11) to (18) (wherein Y is an alkyl group having 1 to 5 carbon atoms, a chlorine atom, a bromine atom, a fluorine atom, or an alkoxy group having 1 to 5 carbon atoms). Represents a hydroxyl group, a carboxyl group, a phenoxy group, a trifluoromethyl group or a nitro group, and m represents a number of 0, 1 or 2.
- a 2 represents a tetravalent organic group
- B 2 represents a divalent organic group.
- a 2 include formulas (3) to (10).
- B 2 include formulas (19) to (27) (wherein Z is an alkyl group having 1 to 5 carbon atoms, a chlorine atom, a bromine atom, a fluorine atom, or an alkoxy group having 1 to 5 carbon atoms).
- Z is an alkyl group having 1 to 5 carbon atoms, a chlorine atom, a bromine atom, a fluorine atom, or an alkoxy group having 1 to 5 carbon atoms.
- m represents a number of 0, 1 or 2.
- the weight average molecular weight of the polyamic acid used in the present invention is, for example, 1000 to 100,000 in terms of polystyrene, or 1,000 to 50,000, and preferably 2,000 to 50,000.
- weight average molecular weight is 1000 or less, the solubility of the formed foreign matter removal coating film in the solvent used in the adhesive layer increases, and as a result, intermixing with the adhesive layer (mixing of layers) ) May occur.
- weight average molecular weight is 100,000 or more, the formed foreign matter removing coating film has insufficient solubility in the developer, and a residue may be present after development.
- the method of obtaining the polyamic acid contained in the foreign matter removing coating film forming composition of the present invention is not particularly limited and can be produced by an existing method.
- a polyamic acid can be produced by reacting and polymerizing a diamine compound and a tetracarboxylic acid or a derivative thereof such as a tetracarboxylic dianhydride compound or a dicarboxylic acid dihalide.
- the silyl ester moiety can be decomposed with an acid to produce a polyamic acid.
- the polyamic acid contained in the foreign matter removing coating film forming composition of the present invention can be produced from (a) a tetracarboxylic dianhydride compound and (b) a diamine compound having at least one carboxyl group, (A) a tetracarboxylic dianhydride compound, (b) a diamine compound having at least one carboxyl group, and (c) a diamine compound.
- the (a) tetracarboxylic dianhydride compound used in the production of the polyamic acid used in the present invention is not particularly limited, and these may be used alone or in combination of two or more. it can. Specific examples include pyromellitic dianhydride, 3,3′-, 4,4′-biphenyltetracarboxylic dianhydride, 3,3′-, 4,4′-benzophenone tetracarboxylic dianhydride, Aromatic tetracarboxylic acids such as 3,3′-, 4,4′-diphenyl ether tetracarboxylic dianhydride, 3,3′-, 4,4′-diphenylsulfone tetracarboxylic dianhydride, 1,2, 3,4-cyclobutanetetracarboxylic dianhydride, 1,2-dimethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-tetramethyl-1,2,3 ,
- the diamine compound having at least one carboxyl group used in the production of the polyamic acid used in the present invention is not particularly limited, and these may be used alone or in combination of two or more. be able to. Specific examples include 2,4-diaminobenzoic acid, 2,5-diaminobenzoic acid, 3,5-diaminobenzoic acid, 4,6-diamino-1,3-benzenedicarboxylic acid, 2,5-diamino-1 , 4-benzenedicarboxylic acid, bis (4-amino-3-carboxyphenyl) ether, bis (4-amino-3,5-dicarboxyphenyl) ether, bis (4-amino-3-carboxyphenyl) sulfone, bis (4-amino-3,5-dicarboxyphenyl) sulfone, 4,4′-diamino-3,3′-dicarboxybiphenyl, 4,4′-diamino-3,3
- the (c) diamine compound used in the production of the polyamic acid used in the present invention is not particularly limited, but (b) a diamine compound different from the diamine compound having at least one carboxyl group.
- the diamine compound preferably has no carboxyl group. In addition, these may be used alone or in combination of two or more.
- Specific examples include 2,4-diaminophenol, 3,5-diaminophenol, 2,5-diaminophenol, 4,6-diaminoresorcinol, 2,5-diaminohydroquinone, bis (3-amino-4-hydroxyphenyl) ) Ether, bis (4-amino-3-hydroxyphenyl) ether, bis (4-amino-3,5-dihydroxyphenyl) ether, bis (3-amino-4-hydroxyphenyl) methane, bis (4-amino-) 3-hydroxyphenyl) methane, bis (4-amino-3,5-dihydroxyphenyl) methane, bis (3-amino-4-hydroxyphenyl) sulfone, bis (4-amino-3-hydroxyphenyl) sulfone, bis ( 4-amino-3,5-dihydroxyphenyl) sulfone, 2,2-bis (3-amino -4-hydroxyphenyl) hexafluoropropan
- a diamine compound having at least one carboxyl group and (c) a diamine compound are used in the production of the polyamic acid used in the present invention, (b) a diamine having at least one carboxyl group in the total diamine compounds
- the proportion of the compound is, for example, 1 to 99% by mass, and for example 5 to 80% by mass, or 10 to 60% by mass.
- the proportion of the diamine compound having at least one carboxyl group is less than this, the solubility of the formed foreign matter removing coating film in the developer is insufficient.
- the polyamic acid used in the present invention is (a) a tetracarboxylic dianhydride compound and (b) at least one carboxyl group, or (a) a tetracarboxylic dianhydride compound, (b) at least one carboxyl group.
- the diamine compound is produced from the diamine compound, the ratio of the total number of moles of the diamine compound to the total number of moles of the tetracarboxylic dianhydride compound is 0.8 to 1.2. desirable. As in the normal polycondensation reaction, the closer the molar ratio is to 1, the higher the degree of polymerization of the polyamic acid produced and the higher the molecular weight.
- the reaction temperature of the reaction between the diamine compound and the tetracarboxylic dianhydride compound can be selected from -20 ° C to + 150 ° C, preferably -5 ° C to + 100 ° C.
- a high molecular weight polyamic acid can be obtained at a reaction temperature of 5 ° C. to 40 ° C. and a reaction time of 1 to 48 hours.
- a reaction time of 10 hours or longer at 40 to 80 ° C. is more preferable.
- the reaction of the diamine compound and the tetracarboxylic dianhydride compound can be performed in a solvent.
- Solvents that can be used in this case include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, N-vinylpyrrolidone, N-methylcaprolactam, dimethylsulfoxide, tetramethylurea, pyridine, dimethylsulfone, Hexamethyl sulfoxide, m-cresol, ⁇ -butyrolactone, ethyl acetate, butyl acetate, ethyl lactate, methyl 3-methoxypropionate, methyl 2-methoxypropionate, ethyl 3-methoxypropionate, ethyl 2-methoxypropionate, 3 -Ethyl ethoxypropionate, ethyl 2-ethoxypropionate, ethylene glycol dimethyl ether, diethylene glycol
- the solution containing the polyamic acid thus obtained can be used as it is for the preparation of the foreign matter removing coating film forming composition. Further, the polyamic acid may be precipitated and isolated in a poor solvent such as methanol or ethanol and recovered for use.
- Examples of the polyamic acid contained in the foreign matter removal coating film-forming composition of the present invention include the following polyamic acids (29) to (41) (wherein p 1 , p 2 , p 3 and p 4 represents the proportion of each structure in the polyamic acid).
- (29) to (36) are polyamic acids produced from one kind of tetracarboxylic dianhydride compound and two kinds of diamine compounds
- (37) and (38) are two kinds of tetracarboxylic acid diacids.
- (39) is a polyamic acid produced from two tetracarboxylic dianhydride compounds and two diamine compounds
- And (41) are polyamic acids produced from a kind of tetracarboxylic dianhydride compound and a kind of diamine compound.
- the foreign matter removing coating film forming composition of the present invention may contain a compound having at least two epoxy groups.
- a compound is not particularly limited as long as it is a compound having an epoxy group.
- a polymer having an epoxy group can be used as the compound having at least two epoxy groups.
- any polymer having an epoxy group can be used without particular limitation.
- Such a polymer can be produced by addition polymerization using an addition polymerizable monomer having an epoxy group, and a reaction between a polymer compound having a hydroxyl group and a compound having an epoxy group such as epichlorohydrin or glycidyl tosylate.
- addition polymerization polymers such as polyglycidyl acrylate, a copolymer of glycidyl methacrylate and ethyl methacrylate, a copolymer of glycidyl methacrylate, styrene and 2-hydroxyethyl methacrylate, and a condensation polymerization polymer such as epoxy novolac.
- the weight average molecular weight of such a polymer is, for example, 300 to 200000.
- Examples of the compound having at least two epoxy groups include YH-434 and YH434L (trade name, manufactured by Tohto Kasei Co., Ltd.) as epoxy resins having amino groups, and Epolede GT as an epoxy resin having a cyclohexene oxide structure.
- YH-434 and YH434L trade name, manufactured by Tohto Kasei Co., Ltd.
- Epolede GT as an epoxy resin having a cyclohexene oxide structure.
- -401, GT-403, GT-301, GT-302, Celoxide 2021, Celoxide 3000 (manufactured by Daicel Chemical Co., Ltd., trade name), and bisphenol A type epoxy resins include Epicoat 1001, 1002, and the like.
- Examples of the epoxy resin include EOCN-102, EOCN-103S, EOCN-104S, EOCN-1020, EOCN-1025, EOCN-1027 (above, Nippon Kayaku Co., Ltd., trade name), Epicoat 180S75 (Oilized Shell Epoxy)
- a cycloaliphatic epoxy resin Denacol EX-252 (trade name, manufactured by Nagase ChemteX Corp.), CY175, CY177, CY179 (above, CIBA-GEIGYGAG) Manufactured, trade name), Araldite CY-182, CY-192, CY-184 (above, CIBA) -GEIGY A.G, trade name), Epicron 200, 400 (above, Dainippon Ink Industries, trade name), Epicoat 871, 872 (above, Yuka Shell Epoxy Co., Ltd., product) No.), ED-5661, ED-5661 (trade name, manufactured by Celanese Coating Co., Ltd
- the content of the compound having at least two epoxy groups is, for example, 5 to 70 parts by mass, or 10 to 60 parts by mass, preferably 15 to 45 parts by mass with respect to 100 parts by mass of the polyamic acid. .
- the degree of cure of the coating film for removing foreign matter is insufficient, and for example, it may dissolve in the adhesive layer and cause intermixing. If it exceeds 70 parts by mass, sufficient solubility in the developer cannot be obtained.
- the coating film forming composition for removing foreign matter of the present invention can be easily prepared by uniformly mixing the above components, and is used in a solution state after being dissolved in an appropriate solvent.
- solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate.
- the thus prepared foreign matter removing coating film resin composition solution is preferably used after being filtered using a filter having a pore size of about 0.2 ⁇ m.
- the foreign matter removing coating film resin composition solution thus prepared is also excellent in long-term storage stability at room temperature.
- the coating film forming composition for removing foreign matter according to the present invention can contain a light-absorbing compound, a surfactant and the like as optional components in addition to the polyamic acid, the compound having at least two epoxy groups and a solvent. .
- the light absorbing compound is not particularly limited as long as it is a compound having absorption at the exposure wavelength to be used.
- a compound having an aromatic ring structure such as an anthracene ring, naphthalene ring, benzene ring, quinoline ring or triazine ring is preferably used.
- a compound having a phenolic hydroxyl group, a carboxyl group or a sulfonic acid group is preferably used.
- Examples of the light-absorbing compound having a large absorption with respect to light having a wavelength of 248 nm include 1-naphthalenecarboxylic acid, 2-naphthalenecarboxylic acid, 1-naphthol, 2-naphthol, 1-aminonaphthalene, 1-hydroxy-2- Naphthalenecarboxylic acid, 3-hydroxy-2-naphthalenecarboxylic acid, 3,7-dihydroxy-2-naphthalenecarboxylic acid, 6-bromo-2-hydroxynaphthalene, 1,2-naphthalenedicarboxylic acid, 1,3-naphthalenedicarboxylic acid 1,4-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 1,6-naphthalenedicarboxylic acid, 1,7-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 6-Naphthalenedi
- Examples of the light-absorbing compound having large absorption with respect to light having a wavelength of 193 nm include benzoic acid, 4-methylbenzoic acid, o-phthalic acid, m-phthalic acid, p-phthalic acid, and 2-methoxybenzoic acid.
- absorptive compounds can be used by reacting with a polymer or a compound having one or more reactive groups in order to suppress sublimation during firing for forming a coating film for removing foreign substances.
- Ar represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, It represents a benzene ring, naphthalene ring or anthracene ring which may be substituted with a thioalkyl group having 1 to 5 carbon atoms, a carboxyl group, a phenoxy group, an acetyl group, an alkoxycarbonyl group having 1 to 5 carbon atoms or a vinyl group.
- the above absorbent compounds can be used alone or in combination of two or more.
- the content thereof is, for example, 1 to 300 parts by mass, or 1 to 200 parts by mass, for example 1 to 100 parts by mass with respect to 100 parts by mass of the polyamic acid. Or 5 to 100 parts by mass.
- the absorbent compound exceeds 300 parts by mass, the solubility of the foreign matter removing coating film in the developer may be reduced, or the foreign matter removing coating film may intermix with the adhesive layer.
- the foreign matter removing coating film forming composition of the present invention can contain an acid generator.
- the acid generator include thermal acid generators such as 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and other organic sulfonic acid alkyl esters, bis (4-tert- And photoacid generators such as butylphenyl) iodonium trifluoromethanesulfonate, triphenylsulfonium trifluoromethanesulfonate, phenyl-bis (trichloromethyl) -s-triazine, benzoin tosylate, and N-hydroxysuccinimide trifluoromethanesulfonate.
- the amount of the acid generator added is 10% by mass or less, preferably 3% by mass or less, if necessary, in the solid content of the coating film forming composition for removing foreign matter.
- the polyphenol compound and the carboxyl group-containing compound can be added to the foreign matter removing coating film forming composition of the present invention for the purpose of accelerating the dissolution rate in the developer.
- a compound is not particularly limited, and examples thereof include tris-hydroxyphenylethane, bisphenol-A, bisphenol-S, 4,4′-isopropylidene-di-o-cresol, and 5-tert-butyl pyrogallol.
- Diphenol bisphenol-AP, bisphenol-P, 5- ⁇ , ⁇ -dimethyl-4-hydroxybenzylsalicylic acid, ⁇ , ⁇ , ⁇ '-tris (4-hydroxyphenyl) -1-ethyl-4-isopropylbenzene, Multivalent phenols such as 5,5′-di-tert-butyl-2,2 ′, 4,4′-tetrahydroxybenzophenone , Pyromellitic acid, phthalic acid, trimeric acid, 4-sulfophthalic acid, benzenehexacarboxylic acid, 2,3-naphthalenedicarboxylic acid, 4-hydroxyphthalic acid, 3,4-dihydroxyphthalic acid, 4,5-dihydroxy Phthal
- an acid such as tert-butyl group, tetrahydropyranyl group, 1-ethoxyethyl group and trimethylsilyl group is used for the purpose of adjusting the dissolution rate in the developer.
- a compound having a carboxyl group or a phenolic hydroxyl group protected with a group that is easily decomposed in the presence can be added.
- Examples of such compounds include di-tert-butyl malonate, tert-butyl acetate, tert-butyl propionate, tert-butyl acetoacetate, tert-amyl acetate, benzoic acid-tert-butyl ester and tert-butyl pivalate. And the like. Further, compounds of formulas (46) to (54) can be exemplified.
- These compounds can easily form a carboxyl group or a phenolic hydroxyl group in the presence of an acid, and give a compound having increased solubility in an alkaline developer. Therefore, these compounds are preferably added together with the photoacid generator to the foreign matter removing coating film forming composition.
- foreign matter removal formed from the foreign matter removal coating film forming composition comprising a compound having a carboxyl group or phenolic hydroxyl group protected with a group that is easily decomposed in the presence of the acid and a photoacid generator
- a compound having a carboxyl group or a phenolic hydroxyl group protected by a group that is easily decomposed in the presence of an acid by an acid generated from a photoacid generator upon exposure in the exposed portion As a result, the solubility of the exposed portion of the foreign matter removing coating film in the alkaline solution is increased.
- the unexposed part there is no change in the compound having a carboxyl group or a phenolic hydroxyl group protected with a group that is easily decomposed in the presence of an acid, and the alkaline solution of the coating film for removing foreign matters in the part is not changed. It does not increase the solubility in water. Therefore, by using a photoacid generator together with a compound having a carboxyl group or phenolic hydroxyl group protected with a group that is easily decomposed in the presence of an acid, an exposed portion of the coating film for removing foreign matter after exposure Therefore, it is possible to make a difference in the solubility of the non-exposed portion with respect to the alkaline developer, thereby facilitating pattern formation by development.
- the content thereof is, for example, 50 to 100 parts by mass with respect to 100 parts by mass of the polyamic acid. 1 part by mass, or 30 to 5 parts by mass, and for example 20 to 10 parts by mass.
- a photoacid generator is used with a compound having a carboxyl group or phenolic hydroxyl group protected with a group that is easily decomposed in the presence of an acid, its content is easily decomposed in the presence of an acid.
- the foreign matter removing coating film forming composition of the present invention can contain a surfactant.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene nonylphenol ether.
- Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as tan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, EFTTOP EF301, EF303, EF352 (Trade name, manufactured by Tochem Products Co., Ltd.), MegaFuck F171, F173 (trade name, manufactured by Dainippon Ink & Chemicals, Inc.), Florad FC430, FC431 (trade name, manufactured by Sumitomo 3M Limited), Asahi Fluorosurfactants such as Guard AG710, Surflon S-382, SC101, SC102, SC103, SC104, SC105, SC106 (trade name, manufactured by Asahi Glass Co., Ltd.), organosiloxane polymer KP341 (Shin-Ets
- the compounding amount of these surfactants is usually 0.2% by mass or less, preferably 0.1% by mass or less, based on all components of the coating film forming composition for removing foreign matter of the present invention.
- These surfactants may be added alone or in combination of two or more.
- the foreign matter removing coating film forming composition of the present invention may further contain a rheology adjusting agent, an adhesion auxiliary agent and the like as necessary.
- the composition for forming a coating film for removing foreign matter according to the present invention on a semiconductor substrate for example, a silicon / silicon dioxide coated substrate, a silicon nitride substrate, a glass substrate, an ITO substrate, etc.
- a coating method such as a spinner, coater, or dipping.
- An object is applied and then fired to form a foreign matter removing coating film.
- the conditions for firing are appropriately selected from firing temperatures of 80 ° C. to 300 ° C. and firing times of 0.3 to 60 minutes.
- the film thickness of the foreign matter removing coating film of the present invention is usually 1 ⁇ m to 5 nm, preferably 500 to 10 nm, and most preferably 300 to 15 nm.
- the dissolution rate of the formed foreign matter removing coating film in the photoresist developer is 0.1 nm to 50 nm per second, preferably 0.2 nm to 40 nm per second, and more preferably 0.3 to 20 nm. .
- the dissolution rate is smaller than this, the time required for removing the foreign matter removing coating film becomes longer, leading to a decrease in productivity.
- the foreign matter removing coating film formed from the foreign matter removing coating film forming composition of the present invention can control the dissolution rate of the foreign matter removing coating film in the developer by changing the baking conditions at the time of formation. It is. In the case of a fixed baking time, the higher the baking temperature, the more the foreign matter removing coating film can be formed with a lower dissolution rate in the developer.
- the foreign matter removing coating film of the present application may be exposed after the film is formed.
- the exposure may be performed on the entire surface of the wafer or through a mask having a predetermined pattern.
- a KrF excimer laser (wavelength 248 nm), an ArF excimer laser (wavelength 193 nm), an F2 excimer laser (wavelength 157 nm), or the like can be used.
- post-exposure heating PEB: Post-Exposure-Bake
- PEB Post-Exposure-Bake
- Developers include aqueous solutions of alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, aqueous solutions of quaternary ammonium hydroxides such as tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline, ethanolamine, propylamine, An alkaline aqueous solution such as an aqueous amine solution such as ethylenediamine can be mentioned as an example. Further, a surfactant or the like can be added to these developers.
- the conditions for removing the foreign matter removing coating film are appropriately selected from a temperature of 5 ° C. to 50 ° C., a time of 2 to 500 seconds, or a time of 3 to 400 seconds.
- the foreign matter removing coating film formed from the foreign matter removing coating film forming composition of the present invention can be easily used at room temperature (for example, 25 ° C.) using a 2.38 mass% aqueous tetramethylammonium hydroxide solution. Peeling can be performed.
- the coating film for removing foreign matter according to the present invention can be optimally adjusted for film removal conditions because the dissolution rate in the developer changes depending on the baking temperature of the film. For example, when using a substrate that lacks resistance to the developer, the film can be removed in a short time by lowering the baking temperature of the film, thereby minimizing damage to the substrate. it can. For example, when firing at 190 ° C. as described in Examples 1 to 4, the film can be removed within 5 seconds.
- the foreign matter removing method of the present application includes a step of applying the composition on a substrate and baking to form a coating film, a step of forming foreign matter on the film, and a developer to act on the film to form the film.
- a foreign matter removing method including a removing step.
- a step of forming an adhesive layer and then peeling the adhesive layer may be further included.
- the foreign matter may be a peeling residue after forming the adhesive layer.
- the substrate examples include glass, metal-containing compounds, and metalloid-containing compounds.
- the metal-containing compound or metalloid-containing compound is, for example, a metal oxide as a basic component, a ceramic, a semiconductor such as silicon, a metal oxide or metalloid oxide (silicon Oxides, alumina, etc.), metal solids or metalloid carbides, metal nitrides or metalloid nitrides (silicon nitride, etc.), inorganic solid materials such as molded bodies of inorganic compounds such as metal borides or metalloid borides, aluminum , Nickel titanium, and stainless steel (SUS304, SUS316, SUS316L, etc.) are preferable, and a silicon substrate (for example, a silicon wafer for semiconductors used for manufacturing semiconductor devices) is preferable.
- ⁇ Substrate processing method> Applying the above composition onto a substrate and baking to form a coating film; forming an adhesive layer on the film; temporarily attaching another substrate to the substrate; It is a substrate processing method including the process of peeling and the process of peeling this film
- the substrate processing method of the present application is applied to, for example, a so-called wafer temporary bonding process.
- the adhesive layer is formed by a known adhesive and method.
- the adhesive include a wafer temporary adhesive of a coating type described in International Publication No. 2015/190438, a temporary bonding material of Thin Materials Co., Ltd. (Nissan Chemical Industry Co., Ltd.), and a semiconductor wafer temporary bonding manufactured by Toray Industries, Inc.
- WaferBOND registered trademark
- CR-200, HT-10.10 made by Brewer Science Co., Ltd.
- a tape-like adhesive for example, a backgrinding tape (for example, 3M TM temporary fixing pressure-sensitive adhesive tape) ATT-4025 (manufactured by 3M Japan Co., Ltd.), E series, P series, S series (manufactured by Lintec Co., Ltd., trade name), Icros tape (registered trademark) (manufactured by Mitsui Chemicals, Inc.)), dicing tape ( For example, solvent-resistant dicing tape (trade name, manufactured by Nitto Denko Corporation), temperature-sensitive viscosity Sheet Intelimer (registered trademark) tape (made by Nitta Co., Ltd.), Intelimer (registered trademark) may be used tape (anchor Techno Co., Ltd.), and the like). It may also be a wafer adhesive applied in a specific wafer handling system (eg Zero Newton
- the back grind tape is composed of a base film, an adhesive layer, and a release film.
- a soft thermoplastic film such as ethylene-vinyl acetate copolymer (EVA) has been used for some time, but a rigid film such as polyethylene terephthalate (PET) is used for the purpose of improving the support of the wafer.
- PET polyethylene terephthalate
- stretched films After that, further improvements were made, and a laminate design of two types of films with different elastic moduli, such as a laminate design of PET and ethylene copolymer, and a laminate design of polypropylene (PP) and ethylene copolymer were reported. Yes.
- Acrylic is generally used as the adhesive.
- the acrylic pressure-sensitive adhesive is known to be designed to crosslink by reacting an acrylic copolymer mainly composed of a monomer having a low glass transition temperature such as butyl acrylate and a curing agent. Since the back grind tape is used by being affixed to the wafer circuit surface, there is a concern about contamination due to the adhesive after the tape is peeled off. For this reason, even if the adhesive remains, it has been reported that it is washed and removed with water, and a design using an emulsion adhesive is reported, but complete removal is difficult.
- an adhesive layer is formed so that foreign matter (adhesive residue) in the subsequent peeling process can be completely removed by washing with a developer, etc. There will be no damage to the wiring.
- the substrate is subjected to a process including a step of applying the above composition onto a substrate and baking to form a coating film, a step of forming an adhesive layer on the film, and a step of attaching the other substrate to the substrate.
- a laminated substrate having the structure of the film-adhesive layer-substrate can be produced.
- one is a semiconductor substrate
- the other is a support substrate for maintaining the shape of the semiconductor substrate
- the adhesive layer is preferably, for example, such that the semiconductor substrate and the support substrate can be peeled again.
- the adhesive layer is as described above.
- Example 1 (Synthesis of polyamic acid) Pyromellitic dianhydride 4.36 g, diaminobenzoic acid 1.19 g, 2,2-bis (3-amino-4-toluyl) hexafluoropropane 4.26 g in propylene glycol monomethyl ether 55.6 g at 60 ° C. By reacting for a time, a solution [A] containing polyamic acid was obtained.
- a solution [1] of a coating film forming composition for removing foreign matter was prepared by adding 67.5 g of monomethyl ether acetate and stirring at room temperature for 30 minutes.
- the refractive index (n value) at a wavelength of 248 nm is 1.67
- the attenuation coefficient (k value) is 0.39
- the refractive index at a wavelength of 193 nm (n value). was 1.53 and the attenuation coefficient (k value) was 0.42.
- the coating film for a foreign material removal was similarly formed by making baking temperature into 190 degreeC, 210 degreeC, and 220 degreeC. It was confirmed that these foreign matter removing coating films were insoluble in ethyl lactate and propylene glycol monomethyl ether acetate.
- the dissolution rate of the foreign matter-removing coating film in the developer (trade name NMD-3, manufactured by Tokyo Ohka Kogyo Co., Ltd.) was measured using a resist development analyzer (manufactured by Risotech Japan Co., Ltd.). The temperature around the analyzer was 25 ° C.
- the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 190 ° C. and a firing time of 60 seconds was 10.7 nm per second.
- the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 200 ° C. and a firing time of 60 seconds is 2.0 nm per second, and the dissolution rate of the foreign matter removal coating film formed at a firing temperature of 210 ° C.
- the dissolution rate of the foreign matter removing coating film formed at 0.9 nm, the baking temperature of 220 ° C., and the baking time of 60 seconds was 0.61 nm per second. That is, a foreign matter removing coating film formed at a firing temperature of 190 ° C. and a firing time of 60 seconds is 3.7 seconds, a foreign matter removing coating film formed at a firing temperature of 200 ° C. and a firing time of 60 seconds is 20 seconds, and a firing temperature of 210
- the foreign matter removing coating film formed at a baking temperature of 60 ° C. for about 44.4 seconds can be completely removed in about 65.6 seconds for the foreign matter removing coating film formed at a baking temperature of 220 ° C.
- the coating solution forming composition [1] for removing foreign matter is applied onto a silicon wafer substrate using a spinner and then baked on a hot plate at 220 ° C. for 60 seconds to form a coating film for removing foreign matter having a thickness of 40 nm. did.
- a positive photoresist film for KrF was formed on the resulting foreign matter removal coating film, and exposed with a KrF excimer laser (wavelength 248 nm) through a mask set to form a 200 nm line / space pattern.
- Example 2 (Preparation of coating film forming composition for removing foreign matter) 4.38 g of the solution [a] containing the light-absorbing compound used in Example 1 in 14.0 g of the polyamic acid solution [A] used in Example 1, 0.630 g of tris (2,3-epoxypropyl) isocyanurate, Add 0.0450 g of 2,4,6-tris (4-hydroxyphenylmethyl) -1,3-benzenediol, 52.8 g of propylene glycol monomethyl ether, and 67.5 g of propylene glycol monomethyl ether acetate, and stir at room temperature for 30 minutes. As a result, a solution [2] of the coating film forming composition for removing foreign matter was prepared.
- the refractive index (n value) at a wavelength of 248 nm is 1.67
- the attenuation coefficient (k value) is 0.39
- the refractive index at a wavelength of 193 nm (n value). was 1.53 and the attenuation coefficient (k value) was 0.42.
- the coating film for a foreign material removal was similarly formed by making baking temperature into 190 degreeC, 210 degreeC, and 220 degreeC. It was confirmed that these foreign matter removing coating films were insoluble in ethyl lactate and propylene glycol monomethyl ether acetate.
- the dissolution rate of the foreign matter-removing coating film in the developer (trade name NMD-3, manufactured by Tokyo Ohka Kogyo Co., Ltd.) was measured using a resist development analyzer (manufactured by Risotech Japan Co., Ltd.). The temperature around the analyzer was 25 ° C.
- the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 190 ° C. and a firing time of 60 seconds was 11.7 nm per second.
- the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 200 ° C. and a firing time of 60 seconds is 2.3 nm per second, and the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 210 ° C.
- the dissolution rate of the foreign matter removing coating film formed at 1.1 nm, baking temperature 220 ° C. and baking time 60 seconds was 0.83 nm per second. That is, the foreign matter removal coating film formed at a firing temperature of 190 ° C. and a firing time of 60 seconds is about 3.4 seconds, and the foreign matter removal coating film formed at a firing temperature of 200 ° C. and a firing time of 60 seconds is about 17.4 seconds.
- the foreign matter removal coating film formed at a firing temperature of 210 ° C. and a firing time of 60 seconds is about 36.4 seconds, and the foreign matter removal coating film formed at a firing temperature of 220 ° C. and a firing time of 60 seconds is about 48.2 seconds.
- the coating solution forming composition [2] for removing foreign matter is applied onto a silicon wafer substrate using a spinner and then baked on a hot plate at 220 ° C. for 60 seconds to form a coating film for removing foreign matter having a thickness of 40 nm. did.
- a positive photoresist film for KrF was formed on the resulting foreign matter removal coating film, and exposed with a KrF excimer laser (wavelength 248 nm) through a mask set to form a 200 nm line / space pattern.
- Example 3 (Synthesis of polyamic acid) Pyromellitic dianhydride 4.36 g, diaminobenzoic acid 0.89 g, 2,2-bis (3-amino-4-toluyl) hexafluoropropane 4.97 g in propylene glycol monomethyl ether 55.6 g at 60 ° C. By reacting for a time, a solution [B] containing polyamic acid was obtained.
- the foreign substance removal coating film forming composition solution [3] is applied onto a silicon wafer substrate using a spinner and then baked on a hot plate at 200 ° C. for 60 seconds to form a foreign substance removal coating film having a thickness of 40 nm. Formed.
- the resulting foreign matter removal coating film was insoluble in ethyl lactate and propylene glycol monomethyl ether acetate.
- the refractive index (n value) at a wavelength of 248 nm is 1.67
- the attenuation coefficient (k value) is 0.39
- the refractive index at a wavelength of 193 nm (n value). was 1.53 and the attenuation coefficient (k value) was 0.42.
- the coating film for a foreign material removal was similarly formed by making baking temperature into 190 degreeC, 210 degreeC, and 220 degreeC. It was confirmed that these foreign matter removing coating films were insoluble in ethyl lactate and propylene glycol monomethyl ether acetate.
- the dissolution rate of the foreign matter-removing coating film in the developer (trade name NMD-3, manufactured by Tokyo Ohka Kogyo Co., Ltd.) was measured using a resist development analyzer (manufactured by Risotech Japan Co., Ltd.). The temperature around the analyzer was 25 ° C.
- the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 190 ° C. and a firing time of 60 seconds was 9.7 nm per second.
- the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 200 ° C. and a firing time of 60 seconds is 1.7 nm per second, and the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 210 ° C.
- the dissolution rate of the foreign matter removing coating film formed at 0.7 nm, the baking temperature of 220 ° C., and the baking time of 60 seconds was 0.53 nm per second. That is, the foreign matter removing coating film formed at a firing temperature of 190 ° C. and a firing time of 60 seconds is about 4.1 seconds, and the foreign matter removing coating film formed at a firing temperature of 200 ° C. and a firing time of 60 seconds is about 23.5 seconds.
- the foreign matter removal coating film formed at a firing temperature of 210 ° C. and a firing time of 60 seconds is about 57.1 seconds, and the foreign matter removal coating film formed at a firing temperature of 220 ° C.
- a firing time of 60 seconds is about 75.5 seconds. Since it can be completely removed, the foreign matter present on the foreign matter removing coating film can also be removed.
- the solution [3] of the foreign matter removing coating film forming composition is applied onto a silicon wafer substrate using a spinner, it is baked on a hot plate at 210 ° C. for 60 seconds to form a foreign matter removing coating film having a thickness of 40 nm. did.
- a positive photoresist film for KrF was formed on the resulting foreign matter removal coating film, and exposed with a KrF excimer laser (wavelength 248 nm) through a mask set to form a 200 nm line / space pattern.
- Example 4 (Preparation of coating film forming composition for removing foreign matter) 4.38 g of the solution [a] containing the light-absorbing compound used in Example 1 to 14.0 g of the polyamic acid solution [A] used in Example 1, 0.630 g of 4,4′-methylenebis (diglycidylaniline) ( Toto Kasei Co., Ltd.), 52.8 g of propylene glycol monomethyl ether and 67.5 g of propylene glycol monomethyl ether acetate were added and stirred at room temperature for 30 minutes to prepare a solution [4] of a coating film forming composition for removing foreign matter.
- 4′-methylenebis diglycidylaniline
- the foreign substance removal coating film forming composition solution [4] is applied onto a silicon wafer substrate using a spinner and then baked on a hot plate at 200 ° C. for 60 seconds to form a foreign substance removal coating film having a thickness of 40 nm. Formed.
- the resulting foreign matter removal coating film was insoluble in ethyl lactate and propylene glycol monomethyl ether acetate.
- the refractive index (n value) at a wavelength of 248 nm is 1.67
- the attenuation coefficient (k value) is 0.39
- the refractive index at a wavelength of 193 nm (n value). was 1.53 and the attenuation coefficient (k value) was 0.42.
- the coating film for a foreign material removal was similarly formed by making baking temperature into 190 degreeC, 210 degreeC, and 220 degreeC. It was confirmed that these foreign matter removing coating films were insoluble in ethyl lactate and propylene glycol monomethyl ether acetate.
- the dissolution rate of the foreign matter-removing coating film in the developer (trade name NMD-3, manufactured by Tokyo Ohka Kogyo Co., Ltd.) was measured using a resist development analyzer (manufactured by Risotech Japan Co., Ltd.). The temperature around the analyzer was 25 ° C.
- the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 190 ° C. and a firing time of 60 seconds was 9.7 nm per second.
- the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 200 ° C. and a firing time of 60 seconds is 0.55 nm per second, and the dissolution rate of the foreign matter removal coating film formed at a firing temperature of 210 ° C.
- the dissolution rate of the foreign matter removing coating film formed at 0.37 nm, a baking temperature of 220 ° C., and a baking time of 60 seconds was 0.13 nm per second. That is, the foreign matter removing coating film formed at a firing temperature of 190 ° C. and a firing time of 60 seconds is about 4.1 seconds, and the foreign matter removing coating film formed at a firing temperature of 200 ° C. and a firing time of 60 seconds is about 72.7 seconds.
- the foreign matter removal coating film formed at a firing temperature of 210 ° C. and a firing time of 60 seconds is about 108.1 seconds, and the foreign matter removal coating film formed at a firing temperature of 220 ° C.
- a firing time of 60 seconds is about 307.7 seconds. Since it can be completely removed, the foreign matter present on the foreign matter removing coating film can also be removed.
- the solution [4] of the foreign matter removal coating film forming composition is applied onto a silicon wafer substrate using a spinner, it is baked on a hot plate at 210 ° C. for 60 seconds to form a foreign matter removal coating film having a thickness of 40 nm. did.
- a positive photoresist film for KrF was formed on the resulting foreign matter removal coating film, and exposed with a KrF excimer laser (wavelength 248 nm) through a mask set to form a 200 nm line / space pattern.
- the refractive index (n value) at a wavelength of 248 nm is 1.80
- the attenuation coefficient (k value) is 0.44
- the refractive index at a wavelength of 193 nm (n value). was 1.50
- the attenuation coefficient (k value) was 0.44
- the coating film for foreign material removal was similarly formed by making baking temperature into 170 degreeC and 180 degreeC. It was confirmed that these foreign matter removing coating films were insoluble in ethyl lactate and propylene glycol monomethyl ether acetate.
- the dissolution rate of the foreign matter-removing coating film in the developer (trade name NMD-3, manufactured by Tokyo Ohka Kogyo Co., Ltd.) was measured using a resist development analyzer (manufactured by Risotech Japan Co., Ltd.). The temperature around the analyzer was 25 ° C.
- the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 170 ° C. and a firing time of 60 seconds was 2.35 nm per second, and the dissolution rate of the foreign matter removing coating film formed at a firing temperature of 175 ° C. and a firing time of 60 seconds was 2.2. It was 00 nm.
- a foreign matter removing coating film formed at a firing temperature of 170 ° C. and a firing time of 60 seconds is 17 seconds
- a foreign matter removing coating film formed at a firing temperature of 175 ° C. and a firing time of 60 seconds is 20 seconds
- the solution [5] of the foreign matter removing coating film forming composition is applied on a silicon wafer substrate using a spinner, it is baked on a hot plate at 220 ° C.
- a positive photoresist film for KrF was formed on the resulting foreign matter removal coating film, and exposed with a KrF excimer laser (wavelength 248 nm) through a mask set to form a 200 nm line / space pattern. After 90 seconds post-exposure heating at 110 ° C., paddle for 60 seconds using 2.38% tetramethylammonium hydroxide aqueous solution (trade name NMD-3, manufactured by Tokyo Ohka Kogyo Co., Ltd.) as a photoresist developer. Development was performed. The exposed part of the coating film for removing foreign substances as well as the photoresist was dissolved in the exposed part, and no residual film was seen even at 200 nm line / space.
- the foreign substance removal coating film forming composition solution [6] is applied onto a silicon wafer substrate using a spinner and then baked on a hot plate at 200 ° C. for 60 seconds to form a foreign substance removal coating film having a thickness of 40 nm. Formed.
- the resulting foreign matter removal coating film was insoluble in ethyl lactate and propylene glycol monomethyl ether acetate.
- the refractive index (n value) at a wavelength of 248 nm was 1.68
- the attenuation coefficient (k value) was 0.40
- the refractive index at a wavelength of 193 nm (n value). was 1.53
- the attenuation coefficient (k value) was 0.42.
- the foreign matter removing coating film formed from the foreign matter removing coating film forming composition solution [6] is applied to a 2.38% tetramethylammonium hydroxide aqueous solution (trade name NMD-3, manufactured by Tokyo Ohka Kogyo Co., Ltd.). It was insoluble.
- the foreign substance removing coating film forming composition solution [5] is applied onto a silicon wafer substrate using a spinner and then baked on a hot plate at 160 ° C., 175 ° C. and 190 ° C. for 60 seconds to form a foreign substance having a film thickness of 40 nm. A coating film for removal was formed.
- the present invention relates to a foreign matter removing coating film forming composition, a foreign matter removing method on a substrate, a substrate processing method, and a method for producing a laminated substrate, which can remove foreign matters formed on a substrate by a simple method.
- a coating film forming composition for removing foreign matter which is used in a semiconductor wafer temporary bonding process for manufacturing a semiconductor device, can be provided.
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Abstract
Description
支持基板に貼り付けを行う際、その後の工程(加熱工程、薬液処理工程)に耐性を有する接着剤(ポリマーを含む液状組成物、バックグラインドテープ、ダイシングテープ等)によりウエハーを貼り付け、その後半導体基板を剥離する工程が行われるが、その際に接着剤に含まれる接着層が、基板上に異物(残渣)として残ってしまう場合がある。これは、基板上に予め配線等が形成された半導体基板表面に直接接着層を形成する場合、特に顕著に発生する。
この異物は、公知の有機溶剤、液状薬品等で洗浄等を行っても、完全に取り除けない場合がある。
支持基板と半導体ウエハーとを接着性組成物で接着し、半導体ウエハーの裏面を研磨した後に接着剤をエッチング液で除去する方法が開示されている(特許文献1)。
半導体リソグラフィーにおいて使用される反射防止膜において、フォトレジスト用現像液に溶解し、フォトレジストと同時に現像除去することができる反射防止膜が開示されている(特許文献2)。
なお、本願発明の異物除去用コーティング膜は、基板上の異物除去のためであれば上記仮接着工程に限定されない。
[1] ポリマー及び溶剤を含み、現像液に溶解するコーティング膜を形成し得る、異物除去用コーティング膜形成組成物。
[2] 前記ポリマーが、(a)テトラカルボン酸二無水物化合物と、(b)少なくとも一つのカルボキシル基を有するジアミン化合物とから誘導される構造単位を有するポリアミド酸である、[1]に記載の組成物。
[3] 前記ポリマーが(a)テトラカルボン酸二無水物化合物と、(b)少なくとも一つのカルボキシル基を有するジアミン化合物とから誘導される構造単位、及び
(a)テトラカルボン酸二無水物化合物と、(c)(b)と異なるジアミン化合物とから誘導される構造単位を有するポリアミド酸である、[1]に記載の組成物。
[4] 前記(c)ジアミン化合物が、カルボキシル基を有さないジアミン化合物である、[3]に記載の組成物。
[5] [1]乃至[4]のいずれか1項に記載の組成物からなる塗布膜の焼成物であることを特徴とする異物除去用コーティング膜。
[6] [1]乃至[4]のいずれか1項に記載の組成物を基板上に塗布し焼成してコーティング膜を形成する工程、該コーティング膜上に異物が形成される工程、及び該コーティング膜を異物と共に現像液にて除去する工程を含む、異物除去方法。
[7] 前記異物が形成される工程が、前記コーティング膜上に接着層を形成する工程、及び、その後、前記接着層を剥離する工程を含む、[6]に記載の方法。
[8] 前記異物が、前記接着層の剥離残渣である、[7]に記載の方法。
[9] [1]乃至[4]のいずれか1項に記載の組成物を第一基板上に塗布し焼成して
コーティング膜を形成する工程、
前記コーティング膜上に接着層を形成する工程、
第二基板を前記接着層を介して前記第一基板に仮貼り付けする工程、
前記第二基板を前記第一基板から剥離する工程、及び
前記第二基板の剥離後に前記第一基板上に残存する前記コーティング膜を前記接着層と共に現像液にて除去する工程を含む、基板処理方法。
[10] [1]乃至[4]のいずれか1項に記載の組成物を第一基板上に塗布し焼成してコーティング膜を形成する工程、
前記コーティング膜上に接着層を形成する工程、及び
第二基板を前記第一基板に貼り付ける工程、を含む積層基板の製造方法。
[12] 上記ポリマーが、式(1):
(式中、A1は4価の有機基を表し、B1は3価の有機基を表す)で表される構造を有するポリアミド酸を含むポリマーである、[11]に記載の組成物。
[13] 式(1)で表される構造と、式(2):
(式中、A2は4価の有機基を表し、B2は2価の有機基を表す)で表される構造を有するポリアミド酸とをさらに含むポリマーである、[12]に記載の組成物。
[14] 前記ポリアミド酸が(a)テトラカルボン酸二無水物化合物と(b)少なくとも一つのカルボキシル基を有するジアミン化合物から製造されるポリアミド酸である、[12]に記載の組成物。
[15] 前記ポリアミド酸が(a)テトラカルボン酸二無水物化合物、(b)少なくとも一つのカルボキシル基を有するジアミン化合物、及び(c)ジアミン化合物から製造されるポリアミド酸である、[13]に記載の組成物。
[16] 前記(a)テトラカルボン酸二無水物化合物が少なくとも一つのベンゼン環構造を有するテトラカルボン酸二無水物化合物である、[14]又は[15]に記載の組成物。
[17] 前記(b)少なくとも一つのカルボキシル基を有するジアミン化合物が少なくとも一つのベンゼン環構造を有するジアミン化合物である、[14]又は[15]に記載の組成物。
[18] 前記(c)ジアミン化合物が二つのベンゼン環構造を有するジアミン化合物である、[15]に記載の組成物。
[19] 前記ポリアミド酸の重量平均分子量が1000~50000である、[12]又[13]に記載の組成物。
[20] さらに、少なくとも二つのエポキシ基を有する化合物を含む、[12]又[13]に記載の組成物。
[21] [11]乃至[20]のいずれか1項に記載の組成物を基板上に塗布し焼成することにより形成される異物除去用コーティング膜。
[22] [11]乃至[20]のいずれか1項に記載の組成物を基板上に塗布し焼成してコーティング膜を形成する工程、該コーティング膜上に異物が形成される工程、及び該コーティング膜を現像液にて除去する工程を含む、異物除去方法。
[23] 前記コーティング膜を形成する工程後、接着層を形成し、次いで接着層を剥離する工程をさらに含む、[22]に記載の方法。
[24] 前記異物が、接着層形成後の剥離残渣である、[22]に記載の方法。
[25] [11]乃至[20]のいずれか1項に記載の組成物を基板上に塗布し焼成してコーティング膜を形成する工程、該膜上に接着層を形成する工程、もう一方の基板を該基板に仮貼り付けする工程、もう一方の基板を剥離する工程、及び該膜を現像液にて除去する工程を含む、基板処理方法。
[26] [11]乃至[20]のいずれか1項に記載の組成物を基板上に塗布し焼成してコーティング膜を形成する工程、該膜上に接着層を形成する工程、もう一方の基板を該基板に貼り付ける工程、を含む積層基板の製造方法。
本発明の異物除去用コーティング膜は、特に半導体ウエハーの仮貼り工程で使用される場合、仮貼り後の半導体基板加工プロセス(熱、薬品)に対して耐性を有する。
本発明の異物除去用コーティング膜形成組成物は、現像液に可溶なポリマーを含む。ポリマーは現像液に溶解するものであれば特に制限はないが、半導体ウエハーの仮貼り工程で使用される場合は、仮貼り後の半導体基板加工プロセス(熱、薬品)に対して耐性を有するポリマーであることが好ましい。具体例としてポリアミド酸、オレフィンが反応したビニル重合ポリマー、ポリアミド、ポリエステル、ポリカーボネート、ポリウレタン等が挙げられるが、好ましくは式(1)で表される構造を有するポリアミド酸及び溶剤を含むものである。さらに少なくとも二つのエポキシ基を有する化合物を含むことが好ましい。また、本発明の異物除去用コーティング膜形成組成物は、式(1)で表される構造と式(2)で表される構造とを有するポリアミド酸及び溶剤を含むものである。さらに少なくとも二つのエポキシ基を有する化合物を含むことが好ましい。そして、本発明の異物除去用コーティング膜形成組成物は、任意成分として、吸光性化合物、界面活性剤等を含有するものである。
本発明の異物除去用コーティング膜形成組成物は式(1)で表される構造を有するポリアミド酸、または、式(1)で表される構造と式(2)で表される構造とを有するポリアミド酸を含むものである。
式(1)においてA1は4価の有機基を表し、B1は3価の有機基を表す。A1としては、例えば、式(3)~(10)が挙げられる(式中Xは、炭素数1~5のアルキル基、塩素原子、臭素原子、フッ素原子、炭素数1~5のアルコキシ基、水酸基、カルボキシル基、フェノキシ基、トリフルオロメチル基またはニトロ基を表し、mは0、1又は2の数を表す)。
B2としては、例えば、式(19)~(27)が挙げられる(式中Zは、炭素数1~5のアルキル基、塩素原子、臭素原子、フッ素原子、炭素数1~5のアルコキシ基、水酸基、カルボキシル基、フェノキシ基、トリフルオロメチル基またはニトロ基を表し、mは0、1又は2の数を表す)。
本発明の異物除去用コーティング膜形成組成物は少なくとも二つのエポキシ基を有する化合物を含有してもよい。そのような化合物としては、エポキシ基を有する化合物であれば特に限定はない。例えば、トリス(2,3-エポキシプロピル)イソシアヌレート、1,4-ブタンジオールジグリシジルエーテル、1,2-エポキシ-4-(エポキシエチル)シクロヘキサン、グリセロールトリグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、2,6-ジグリシジルフェニルグリシジルエーテル、1,1,3-トリス[p-(2,3-エポキシプロポキシ)フェニル]プロパン、1,2-シクロヘキサンジカルボン酸ジグリシジルエステル、4,4’-メチレンビス(N,N-ジグリシジルアニリン)、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、トリメチロールエタントリグリシジルエーテル及びビスフェノール-A-ジグリシジルエーテル、ペンタエリスリトールポリグリシジルエーテル等を挙げることができる。
本発明の異物除去用コーティング膜形成組成物は、上記の各成分を均一に混合することによって容易に調製することができ、適当な溶剤に溶解されて溶液状態で用いられる。そのような溶剤としては、例えば、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、メチルセロソルブアセテート、エチルセロソルブアセテート、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールプロピルエーテルアセテート、トルエン、キシレン、メチルエチルケトン、シクロペンタノン、シクロヘキサノン、2-ヒドロキシプロピオン酸エチル、2-ヒドロキシ-2-メチルプロピオン酸エチル、エトキシ酢酸エチル、ヒドロキシ酢酸エチル、2-ヒドロキシ-3-メチルブタン酸メチル、3-メトキシプロピオン酸メチル、3-メトキシプロピオン酸エチル、3-エトキシプロピオン酸エチル、3-エトキシプロピオン酸メチル、ピルビン酸メチル、ピルビン酸エチル、酢酸エチル、酢酸ブチル、乳酸エチル、乳酸ブチル、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等を用いることができる。これらの溶剤は単独または2種以上の組合せで使用することができる。さらに、プロピレングリコールモノブチルエーテル、プロピレングリコールモノブチルエーテルアセテート等の高沸点溶剤を混合して使用することができる。
そのため、これらの化合物は光酸発生剤と共に異物除去用コーティング膜形成組成物に添加されることが好ましい。すなわち、上記の酸の存在下で容易に分解される基で保護されたカルボキシル基又はフェノール性水酸基を有する化合物と光酸発生剤とを含む異物除去用コーティング膜形成組成物から形成された異物除去用コーティング膜にあっては、その露光された部分では露光によって光酸発生剤から発生した酸によって、酸の存在下で容易に分解される基で保護されたカルボキシル基又はフェノール性水酸基を有する化合物のカルボキシル基又はフェノール性水酸基が再生し、その結果、露光された部分の異物除去用コーティング膜のアルカリ性溶液に対する溶解性が高まることとなる。これに対し、露光されていない部分では酸の存在下で容易に分解される基で保護されたカルボキシル基又はフェノール性水酸基を有する化合物に変化はなく、その部分の異物除去用コーティング膜のアルカリ性溶液に対する溶解性を高めることとはならない。このため、酸の存在下で容易に分解される基で保護されたカルボキシル基又はフェノール性水酸基を有する化合物と光酸発生剤を共に使用することにより、露光後の異物除去用コーティング膜の露光部と非露光部のアルカリ性の現像液に対する溶解性に差をつけることができるようになり、現像によるパターン形成を容易なものとする。
半導体基板(例えば、シリコン/二酸化シリコン被覆基板、シリコンナイトライド基板、ガラス基板、ITO基板等)の上に、スピナー、コーター、浸漬等の適当な塗布方法により本発明の異物除去用コーティング膜形成組成物が塗布され、その後、焼成することにより異物除去用コーティング膜が形成される。焼成する条件としては、焼成温度80℃~300℃、焼成時間0.3~60分間の中から適宜、選択される。
本願の異物除去方法は、上記組成物を基板上に塗布し焼成してコーティング膜を形成する工程、該膜上に異物が形成される工程、及び該膜に現像液を作用させて該膜を除去する工程を含む、異物除去方法である。
上記の組成物を基板上に塗布し焼成してコーティング膜を形成する工程、該膜上に接着層を形成する工程、もう一方の基板を該基板に仮貼り付けする工程、もう一方の基板を剥離する工程、及び該膜を現像液で剥離する工程を含む、基板処理方法である。
本願の基板処理方法は、例えばいわゆるウエハー仮貼り工程に適用される。
接着剤層は、公知の接着剤と方法によって形成される。接着剤としては例えば国際公開第2015/190438号等に記載の塗布タイプのウエハー仮接着剤、ThinMaterials社の仮貼り合わせ材料(日産化学工業(株))、東レ株式会社製の半導体用ウエハー仮貼り材料、WaferBOND(登録商標)CR-200、HT-10.10(ブリューワーサイエンス社製)を用いてもよいし、テープ状接着剤(例えば、バックグラインド用テープ(例えば、3MTM仮固定用粘着テープ ATT-4025(スリーエム ジャパン株式会社製)、Eシリーズ、Pシリーズ、Sシリーズ(リンテック株式会社製、商品名)、イクロステープ(登録商標)(三井化学東セロ株式会社製))、ダイシング用テープ(例えば、耐溶剤ダイシングテープ(日東電工株式会社製、商品名)、感温性粘着シート インテリマー(登録商標)テープ(ニッタ株式会社製)、インテリマー(登録商標)テープ(アンカーテクノ株式会社製)等)を用いてもよい。
特定のウエハーハンドリングシステム(例えば、Zero Newton(登録商標)(東京応化工業(株))中に適用されるウエハー用接着剤でもよい。
上記の組成物を基板上に塗布し焼成してコーティング膜を形成する工程、該膜上に接着層を形成する工程、もう一方の基板を該基板に貼り付ける工程、を含む工程を経て、基板―該膜―接着層―基板の構成を有する積層基板が製造できる。好ましくは、一方が半導体基板、もう一方が半導体基板の形状を保持するための支持基板であり、接着層は、例えば半導体基板と支持基板が再度剥離できるものが好ましい。接着層は上記に記載の通りである。
(ポリアミド酸の合成)
ピロメリット酸二無水物4.36g、ジアミノ安息香酸1.19g、2,2-ビス(3-アミノ-4-トルイル)ヘキサフルオロプロパン4.26gをプロピレングリコールモノメチルエーテル55.6g中60℃で25時間反応することによって、ポリアミド酸を含む溶液[A]を得た。
(吸光性化合物の合成)
3、7-ジヒドロキシ-2-ナフトエ酸19.0g、トリス(2,3-エポキシプロピル)イソシアヌレート10g、ベンジルトリエチルアンモニウムクロリド0.552gをシクロヘキサノン118g中130℃で24時間反応させることで吸光性化合物を含む溶液[a]を得た。
(異物除去用コーティング膜形成組成物の調製)
ポリアミド酸を含む溶液[A]14.0gに吸光性化合物を含む溶液[a]4.38g、トリス(2,3-エポキシプロピル)イソシアヌレート0.630g、プロピレングリコールモノメチルエーテル52.3g、プロピレングリコールモノメチルエーテルアセテート67.5gを添加し室温で30分間攪拌することにより異物除去用コーティング膜形成組成物の溶液[1]を調製した。
この異物除去用コーティング膜形成組成物の溶液[1]をシリコンウエハー基板上にスピナーを用いて塗布した後、ホットプレート上で200℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜は乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であった。この異物除去用コーティング膜をエリプソメーターで測定した結果、波長248nmでの屈折率(n値)は1.67、減衰係数(k値)は0.39、波長193nmでの屈折率(n値)は1.53、減衰係数(k値)は0.42であった。
また、焼成温度を190℃、210℃及び220℃として同様に異物除去用コーティング膜を形成した。そして、これらの異物除去用コーティング膜が乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であることを確認した。
次に、現像液(東京応化工業(株)製、商品名NMD-3)に対する異物除去用コーティング膜の溶解速度をレジスト現像アナライザー(リソテックジャパン(株)製)を用いて測定した。アナライザー周辺の温度は25℃であった。焼成温度190℃、焼成時間60秒で形成した異物除去用コーティング膜の溶解速度は毎秒10.7nmであった。また、焼成温度200℃、焼成時間60秒で形成した異物除去用コーティング膜の溶解速度は毎秒2.0nm、焼成温度210℃、焼成時間60秒で形成した異物除去用コーティング膜の溶解速度は毎秒0.9nm、焼成温度220℃、焼成時間60秒で形成した異物除去用コーティング膜の溶解速度は毎秒0.61nmであった。つまり焼成温度190℃、焼成時間60秒で形成した異物除去用コーティング膜は3.7秒で、焼成温度200℃、焼成時間60秒で形成した異物除去用コーティング膜は20秒で、焼成温度210℃、焼成時間60秒で形成した異物除去用コーティング膜は約44.4秒で、焼成温度220℃、焼成時間60秒で形成した異物除去用コーティング膜は約65.6秒で完全に除去できるため、本異物除去用コーティング膜上に存在する異物も除去できることになる。
異物除去用コーティング膜形成組成物の溶液[1]をシリコンウエハー基板上にスピナーを用いて塗布した後、ホットプレート上で220℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜上にKrF用ポジ型フォトレジスト膜を形成し、200nmのライン/スペースパターンが形成されるように設定されたマスクを通して、KrFエキシマレーザー(波長248nm)で露光した。
110℃で90秒間露光後加熱を行った後、フォトレジスト用現像液として2.38%テトラメチルアンモニウムヒドロキシド水溶液(東京応化工業(株)製、商品名NMD-3)を用いて60秒間パドル現像を行った。フォトレジストとともに異物除去用コーティング膜も露光部は溶解し、200nmのライン/スペースでも残膜は見られなかった。
(異物除去用コーティング膜形成組成物の調製)
実施例1で用いたポリアミド酸溶液[A]14.0gに実施例1で用いた吸光性化合物を含む溶液[a]4.38g、トリス(2,3-エポキシプロピル)イソシアヌレート0.630g、2、4,6-トリス(4-ヒドロキシフェニルメチル)-1,3-ベンゼンジオール0.0450g、プロピレングリコールモノメチルエーテル52.8g、プロピレングリコールモノメチルエーテルアセテート67.5gを添加し室温で30分間攪拌することにより異物除去用コーティング膜形成組成物の溶液[2]を調製した。
(異物除去用コーティング膜形成組成物の評価)
この異物除去用コーティング膜形成組成物の溶液[2]をシリコンウエハー基板上にスピナーを用いて塗布した後、ホットプレート上で200℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜は乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であった。この異物除去用コーティング膜をエリプソメーターで測定した結果、波長248nmでの屈折率(n値)は1.67、減衰係数(k値)は0.39、波長193nmでの屈折率(n値)は1.53、減衰係数(k値)は0.42であった。
また、焼成温度を190℃、210℃及び220℃として同様に異物除去用コーティング膜を形成した。そして、これらの異物除去用コーティング膜が乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であることを確認した。
つまり焼成温度190℃、焼成時間60秒で形成した異物除去用コーティング膜は約3.4秒で、焼成温度200℃、焼成時間60秒で形成した異物除去用コーティング膜は約17.4秒で、焼成温度210℃、焼成時間60秒で形成した異物除去用コーティング膜は約36.4秒で、焼成温度220℃、焼成時間60秒で形成した異物除去用コーティング膜は約48.2秒で完全に除去できるため、本異物除去用コーティング膜上に存在する異物も除去できることになる。
異物除去用コーティング膜形成組成物の溶液[2]をシリコンウエハー基板上にスピナーを用いて塗布した後、ホットプレート上で220℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜上にKrF用ポジ型フォトレジスト膜を形成し、200nmのライン/スペースパターンが形成されるように設定されたマスクを通して、KrFエキシマレーザー(波長248nm)で露光した。110℃で90秒間露光後加熱を行った後、フォトレジスト用現像液として2.38%テトラメチルアンモニウムヒドロキシド水溶液(東京応化工業(株)製、商品名NMD-3)を用いて60秒間パドル現像を行った。フォトレジストとともに異物除去用コーティング膜も露光部は溶解し、200nmのライン/スペースでも残膜は見られなかった。
(ポリアミド酸の合成)
ピロメリット酸二無水物4.36g、ジアミノ安息香酸0.89g、2,2-ビス(3-アミノ-4-トルイル)ヘキサフルオロプロパン4.97gをプロピレングリコールモノメチルエーテル55.6g中60℃で25時間反応することでポリアミド酸を含む溶液[B]を得た。
(異物除去用コーティング膜形成組成物の調製)
ポリアミド酸を含む溶液[B]14.0gに実施例1で用いた吸光性化合物を含む溶液[a]4.38g、トリス(2,3-エポキシプロピル)イソシアヌレート0.630g、プロピレングリコールモノメチルエーテル52.4g、プロピレングリコールモノメチルエーテルアセテート67.5gを添加し室温で30分間攪拌することにより異物除去用コーティング膜形成組成物の溶液[3]を調製した。
(異物除去用コーティング膜形成組成物の評価)
この異物除去用コーティング膜形成組成物の溶液[3]をシリコンウエハー基板上にスピナーを用いて塗布した後、ホットプレート上で200℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜は乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であった。この異物除去用コーティング膜をエリプソメーターで測定した結果、波長248nmでの屈折率(n値)は1.67、減衰係数(k値)は0.39、波長193nmでの屈折率(n値)は1.53、減衰係数(k値)は0.42であった。
また、焼成温度を190℃、210℃及び220℃として同様に異物除去用コーティング膜を形成した。そして、これらの異物除去用コーティング膜が乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であることを確認した。
つまり焼成温度190℃、焼成時間60秒で形成した異物除去用コーティング膜は約4.1秒で、焼成温度200℃、焼成時間60秒で形成した異物除去用コーティング膜は約23.5秒で、焼成温度210℃、焼成時間60秒で形成した異物除去用コーティング膜は約57.1秒で、焼成温度220℃、焼成時間60秒で形成した異物除去用コーティング膜は約75.5秒で完全に除去できるため、本異物除去用コーティング膜上に存在する異物も除去できることになる。
異物除去用コーティング膜形成組成物の溶液[3]をシリコンウエハー基板上にスピナーを用いて塗布した後、ホットプレート上で210℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜上にKrF用ポジ型フォトレジスト膜を形成し、200nmのライン/スペースパターンが形成されるように設定されたマスクを通して、KrFエキシマレーザー(波長248nm)で露光した。
110℃で90秒間露光後加熱を行った後、フォトレジスト用現像液として2.38%テトラメチルアンモニウムヒドロキシド水溶液(東京応化工業(株)製、商品名NMD-3)を用いて60秒間パドル現像を行った。フォトレジストとともに異物除去用コーティング膜も露光部は溶解し、200nmのライン/スペースでも残膜は見られなかった。
(異物除去用コーティング膜形成組成物の調製)
実施例1で用いたポリアミド酸溶液[A]14.0gに実施例1で用いた吸光性化合物を含む溶液[a]4.38g、4,4’-メチレンビス(ジグリシジルアニリン)0.630g(東都化成製)、プロピレングリコールモノメチルエーテル52.8g、プロピレングリコールモノメチルエーテルアセテート67.5gを添加し室温で30分間攪拌することにより異物除去用コーティング膜形成組成物の溶液[4]を調製した。
(異物除去用コーティング膜形成組成物の評価)
この異物除去用コーティング膜形成組成物の溶液[4]をシリコンウエハー基板上にスピナーを用いて塗布した後、ホットプレート上で200℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜は乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であった。この異物除去用コーティング膜をエリプソメーターで測定した結果、波長248nmでの屈折率(n値)は1.67、減衰係数(k値)は0.39、波長193nmでの屈折率(n値)は1.53、減衰係数(k値)は0.42であった。
また、焼成温度を190℃、210℃及び220℃として同様に異物除去用コーティング膜を形成した。そして、これらの異物除去用コーティング膜が乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であることを確認した。
つまり焼成温度190℃、焼成時間60秒で形成した異物除去用コーティング膜は約4.1秒で、焼成温度200℃、焼成時間60秒で形成した異物除去用コーティング膜は約72.7秒で、焼成温度210℃、焼成時間60秒で形成した異物除去用コーティング膜は約108.1秒で、焼成温度220℃、焼成時間60秒で形成した異物除去用コーティング膜は約307.7秒で完全に除去できるため、本異物除去用コーティング膜上に存在する異物も除去できることになる。
異物除去用コーティング膜形成組成物の溶液[4]をシリコンウエハー基板上にスピナーを用いて塗布した後、ホットプレート上で210℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜上にKrF用ポジ型フォトレジスト膜を形成し、200nmのライン/スペースパターンが形成されるように設定されたマスクを通して、KrFエキシマレーザー(波長248nm)で露光した。
110℃で90秒間露光後加熱を行った後、フォトレジスト用現像液として2.38%テトラメチルアンモニウムヒドロキシド水溶液(東京応化工業(株)製、商品名NMD-3)を用いて60秒間パドル現像を行った。フォトレジストとともに異物除去用コーティング膜も露光部は溶解し、200nmのライン/スペースでも残膜は見られなかった。
(ポリアミド酸の合成)
4,4’-(ヘキサフルオロイソプロピリデン)ジフタル酸二無水物17.8g、3,5-ジアミノ安息香酸3.12g及びビス(4-アミノフェニルスルホン)4.92gをプロピレングリコールモノメチルエーテル145.6g中80℃で20時間反応することによって、ポリアミド酸を含む溶液[C]を得た。得られたポリアミド酸のGPC分析を行ったところ、重量平均分子量Mw=8600(標準ポリスチレン換算)、数平均分子量Mn=5200であった。
(異物除去用コーティング膜形成組成物の調製)
ポリアミド酸を含む溶液[C]25.0gに吸光性化合物溶液[a]4.15g、4,4’-メチレンビス(N,N-ジグリシジルアニリン)1.13g、3,7-ジヒドロキシナフトエ酸0.825g、トリフェニルスルホニウムトリフルオロメタンスルホネート0.124g、プロピレングリコールモノメチルエーテル82.8g、プロピレングリコールモノメチルエーテルアセテート127g、シクロヘキサノン10.0gを添加し室温で30分間攪拌することにより異物除去用コーティング膜形成組成物の溶液[5]を調製した。
この異物除去用コーティング膜形成組成物の溶液[5]をシリコンウェハー基板上にスピナーを用いて塗布した後、ホットプレート上で175℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜はプロピレングリコール、乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であった。この異物除去用コーティング膜をエリプソメーターで測定した結果、波長248nmでの屈折率(n値)は1.80、減衰係数(k値)は0.44、波長193nmでの屈折率(n値)は1.50、減衰係数(k値)は0.44であった。
また、焼成温度を170℃及び180℃として同様に異物除去用コーティング膜を形成した。そして、これらの異物除去用コーティング膜が乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であることを確認した。
次に、現像液(東京応化工業(株)製、商品名NMD-3)に対する異物除去用コーティング膜の溶解速度をレジスト現像アナライザー(リソテックジャパン(株)製)を用いて測定した。アナライザー周辺の温度は25℃であった。焼成温度170℃、焼成時間60秒で形成した異物除去用コーティング膜の溶解速度は毎秒2.35nm、焼成温度175℃、焼成時間60秒で形成した異物除去用コーティング膜の溶解速度は毎秒2.00nmであった。焼成温度180℃、焼成時間60秒で形成した異物除去用コーティング膜の溶解速度は毎秒1.82nmであった。
つまり焼成温度170℃、焼成時間60秒で形成した異物除去用コーティング膜は17秒で、焼成温度175℃、焼成時間60秒で形成した異物除去用コーティング膜は20秒で、焼成温度180℃、焼成時間60秒で形成した異物除去用コーティング膜は22秒で完全に除去できるため、本異物除去用コーティング膜上に存在する異物も除去できることになる。
異物除去用コーティング膜形成組成物の溶液[5]をシリコンウェハー基板上にスピナーを用いて塗布した後、ホットプレート上で220℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜上にKrF用ポジ型フォトレジスト膜を形成し、200nmのライン/スペースパターンが形成されるように設定されたマスクを通して、KrFエキシマレーザー(波長248nm)で露光した。110℃で90秒間露光後加熱を行った後、フォトレジスト用現像液として2.38%テトラメチルアンモニウムヒドロキシド水溶液(東京応化工業(株)製、商品名NMD-3)を用いて60秒間パドル現像を行った。フォトレジストとともに異物除去用コーティング膜も露光部は溶解し、200nmのライン/スペースでも残膜は見られなかった。
(ポリアミド酸の合成)
ピロメリット酸二無水物4.36g、p-フェニレンジアミン0.838g、2,2-ビス(3-アミノ-4-トルイル)ヘキサフルオロプロパン4.26gをプロピレングリコールモノメチルエーテル55.6g中60℃で25時間反応することでポリアミド酸溶液[D]を得た。得られたポリアミド酸のGPC分析を行ったところ、重量平均分子量Mw=8600(標準ポリスチレン換算)、数平均分子量Mn=4800であった。
(異物除去用コーティング膜形成組成物の調製)
ポリアミド酸溶液[D]14.0gに実施例1で用いた吸光性化合物溶液[a]4.38g、トリス(2,3-エポキシプロピル)イソシアヌレート0.630g、プロピレングリコールモノメチルエーテル52.3g、プロピレングリコールモノメチルエーテルアセテート67.5gを添加し室温で30分間攪拌することにより異物除去用コーティング膜形成組成物の溶液[6]を調製した。
この異物除去用コーティング膜形成組成物の溶液[6]をシリコンウエハー基板上にスピナーを用いて塗布した後、ホットプレート上で200℃、60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。得られた異物除去用コーティング膜は乳酸エチル及びプロピレングリコールモノメチルエーテルアセテートに不溶であった。この異物除去用コーティング膜をエリプソメーターで測定した結果、波長248nmでの屈折率(n値)は1.68、減衰係数(k値)は0.40、波長193nmでの屈折率(n値)は1.53、減衰係数(k値)は0.42であった。
この異物除去用コーティング膜形成組成物の溶液[6]から形成した異物除去用コーティング膜は、2.38%テトラメチルアンモニウムヒドロキシド水溶液(東京応化工業(株)製、商品名NMD-3)に不溶であった。
(膜形成後の引き置きの影響評価)
異物除去用コーティング膜形成組成物の溶液[5]をシリコンウエハー基板上にスピナーを用いて塗布した後、ホットプレート上で160℃、175℃及び190℃で60秒間焼成して膜厚40nmの異物除去用コーティング膜を形成した。膜形成直後、及びウエハケース内に1日、3日、7日放置したウエハー各々を2.38%テトラメチルアンモニウムヒドロキシド水溶液(東京応化工業(株)製、商品名NMD-3)を用いて60秒間パドル現像を行い、膜が形成されていたウエハー面上の膜厚をエリプソメーターで測定した。その結果、上記全ての条件において、残膜は1nm以下となったことから、膜形成後7日放置した後でも、膜形成直後と同様な膜除去性を有することが確認された。
Claims (10)
- ポリマー及び溶剤を含み、現像液に溶解するコーティング膜を形成し得る、異物除去用
コーティング膜形成組成物。 - 前記ポリマーが、(a)テトラカルボン酸二無水物化合物と、(b)少なくとも一つのカルボキシル基を有するジアミン化合物とから誘導される構造単位を有するポリアミド酸である、請求項1に記載の組成物。
- 前記ポリマーが、(a)テトラカルボン酸二無水物化合物と、(b)少なくとも一つのカルボキシル基を有するジアミン化合物とから誘導される構造単位、及び
(a)テトラカルボン酸二無水物化合物と、(c)(b)と異なるジアミン化合物とから誘導される構造単位を有するポリアミド酸である、請求項1に記載の組成物。 - 前記(c)ジアミン化合物が、カルボキシル基を有さないジアミン化合物である、請求項3に記載の組成物。
- 請求項1乃至請求4のいずれか1項に記載の組成物からなる塗布膜の焼成物であることを特徴とする異物除去用コーティング膜。
- 請求項1乃至請求項4のいずれか1項に記載の組成物を基板上に塗布し焼成してコーティング膜を形成する工程、該コーティング膜上に異物が形成される工程、及び該コーティング膜を異物と共に現像液にて除去する工程を含む、異物除去方法。
- 前記異物が形成される工程が、
前記コーティング膜上に接着層を形成する工程、及び、その後、前記接着層を剥離する工程を含む、請求項6に記載の方法。 - 前記異物が、前記接着層の剥離残渣である、請求項7に記載の方法。
- 請求項1乃至請求項4のいずれか1項に記載の組成物を第一基板上に塗布し焼成して
コーティング膜を形成する工程、
前記コーティング膜上に接着層を形成する工程、
第二基板を前記接着層を介して前記第一基板に仮貼り付けする工程、
前記第二基板を前記第一基板から剥離する工程、及び
前記第二基板の剥離後に前記第一基板上に残存する前記コーティング膜を前記接着層と共
に現像液にて除去する工程を含む、基板処理方法。 - 請求項1乃至請求項4のいずれか1項に記載の組成物を第一基板上に塗布し焼成して
コーティング膜を形成する工程、
前記コーティング膜上に接着層を形成する工程、及び
第二基板を前記第一基板に貼り付ける工程、を含む積層基板の製造方法。
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