WO2007148574A1 - Agent de décapage de resist - Google Patents

Agent de décapage de resist Download PDF

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Publication number
WO2007148574A1
WO2007148574A1 PCT/JP2007/061867 JP2007061867W WO2007148574A1 WO 2007148574 A1 WO2007148574 A1 WO 2007148574A1 JP 2007061867 W JP2007061867 W JP 2007061867W WO 2007148574 A1 WO2007148574 A1 WO 2007148574A1
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WO
WIPO (PCT)
Prior art keywords
resist
acid
stripping
anticorrosion
weight
Prior art date
Application number
PCT/JP2007/061867
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English (en)
Japanese (ja)
Inventor
Yasushi Shiraki
Toyozo Fujioka
Shigeru Matsuo
Original Assignee
Idemitsu Kosan Co., Ltd.
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Publication date
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Priority to JP2008522407A priority Critical patent/JPWO2007148574A1/ja
Publication of WO2007148574A1 publication Critical patent/WO2007148574A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/046—Salts
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3227—Ethers thereof
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • 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
    • H01L21/02057—Cleaning during device manufacture
    • H01L21/0206—Cleaning during device manufacture during, before or after processing of insulating layers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C11D2111/22—Electronic devices, e.g. PCBs or semiconductors

Definitions

  • the present invention relates to a resist stripper.
  • the resist remover of the present invention is excellent in releasability, safe from flammability, and excellent in corrosion resistance that does not corrode the conductor.
  • Integrated circuits such as IC and LSI, display devices such as LCD and EL elements, printed circuit boards, and the like are manufactured using photolithography technology.
  • unnecessary resist photosensitive agent
  • resist stripper unnecessary resist
  • the mainstay is resist strippers containing amine compounds with excellent stripping properties.
  • This amine release agent can be classified into a solvent type and an aqueous type.
  • a solvent based release agent dimethyl sulfoxide (about 30 weight 0/0) + monoethanol ⁇ Min (about 70 weight 0/0) and, like Monoe Tanoruamin + N-methylpyrrolidone is used.
  • an aqueous release agent water (about 20 to 30 wt%) + diethylene glycol monobutyl ether (about 20-30 by weight 0 / o) + monoethanol ⁇ Min (about 30-40 weight 0/0), alkyl benzene sulfonic acid + Functional water (ozone water), acid (sulfuric acid + hydrogen peroxide) + functional water (ozone water) are used.
  • Patent Document 1 discloses a photoresist stripper containing a product obtained by reacting alkanolamine and formaldehyde. This product is produced by reacting an alkanolamine with formaldehyde in a formaldehyde / alkanolamine (molar ratio) at a ratio of 0.8 or less.
  • Patent Document 2 discloses a photoresist stripping composition comprising an alkanolamine compound, a sulfone compound or a sulfoxide compound, and a hydroxy compound.
  • Patent Document 3 discloses a resist remover having a stable pH and containing at least a hydroxycarboxylic acid and water.
  • the hydroxycarboxylic acid contained after the production has a ratio of the condensate of two or more molecules to the hydroxycarboxylic acid monomer (ie, the condensate / monomer) is 1/9 or less. Have been adjusted so that.
  • Patent Document 4 discloses a stripping agent that strips a resist for using an alloy of copper and silver in a wiring process.
  • This resist stripper contains piperazines.
  • Patent Document 5 discloses a resist stripper containing tetraethylenepentamine and ether alcohol.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2004-219486
  • Patent Document 2 JP 05-281753 A
  • Patent Document 3 Japanese Patent Laid-Open No. 2005-049438
  • Patent Document 4 Japanese Unexamined Patent Application Publication No. 2004-205674
  • Patent Document 5 Japanese Unexamined Patent Application Publication No. 2004-205675
  • the technologies described in the above patent documents have been developed for the purpose of improving resist stripping performance and preventing corrosion of conductors (such as wiring made of copper (Cu) or aluminum (A1)). However, there is a problem that these technologies still cannot satisfy both purposes completely.
  • the present invention has been made in view of the above problems, and provides a resist stripper that has excellent releasability, is safe without flammability, and has excellent corrosion resistance that does not corrode conductors. With the goal.
  • the present inventor has made extensive studies in view of the above situation. As a result, a specific novel alkoxyamide compound having high amphiphilic properties was used as a resist stripper. This resist stripper was excellent in anticorrosion properties, and was excellent in both strength and stripping performance. The present invention has been completed in this way.
  • the resist remover of the present invention contains a compound represented by the formula (1).
  • R is an alkyl group having 1 to 18 carbon atoms.
  • R and R are
  • R and R may be the same or different from each other, and
  • the alkoxyamide-based resist stripper has high stripping performance and is extremely excellent in corrosion resistance against copper and aluminum. Further, since this resist stripper is water-soluble, no IPA (isopropyl alcohol) rinse is required, and productivity can be improved.
  • the compound represented by the formula (1) Preferably, about 20 to 100% by weight of the compound represented by the formula (1) and about 0 to 80% by weight of water are included.
  • the resist remover can also be used as a water-mixed resist remover.
  • resist stripping agents can be made non-hazardous by eliminating flammability by using a water mixture. Can be handled.
  • the resist stripper has high stripping performance even at a high water dilution rate, and the amount of resist stripper used can be reduced. Furthermore, even when the resist stripping agent is not a water mixture, the safety can be improved because the alkoxyamide compound itself has a high flash point.
  • the carbon numbers of R and R are:! -4.
  • the resist stripping agent can suppress that the solubility to water falls, and water rinse becomes possible.
  • the carbon number of R and R is 1, and the carbon number of R is:
  • the resist stripper can suppress the decrease in water solubility without decreasing the resist strippability.
  • the carbon number of R and R is 2, and the carbon number of R is:! -6
  • the resist stripper can suppress the decrease in water solubility without decreasing the resist strippability.
  • an anticorrosive agent a chelating agent, a peeling accelerator, a reducing agent, an oxidizing agent, a surfactant, a buffering agent and / or an antioxidant are added.
  • the resist stripper can suppress performance deterioration due to oxidation.
  • FIG. 1 shows Table 1 showing release agent types (composition of the release liquid), release performance and anticorrosion performance for Examples 1 to 15.
  • FIG. 2 shows Table 2 showing the release agent type (composition of the release solution), release performance and anticorrosion performance for Comparative Examples:!
  • the resist remover of the present invention is used in the production of liquid crystal display panels and semiconductor elements. It is. That is, the resist (photosensitive agent) that is no longer necessary in the photolithography process is dissolved and removed.
  • the resist stripper of this embodiment is configured to include an alkoxyamide compound represented by the formula (1).
  • R is an alkyl group having 1 to 18 carbon atoms.
  • R and R are
  • a monovalent hydrocarbon group which may have a hydrogen atom or an ether bond having 1 to 6 carbon atoms.
  • examples of the alkyl group of R include a methylol group, an ethyl group, various propyl groups, and various butylenes.
  • This alkyl group is particularly preferably one having 1 to 6 carbon atoms, preferably one having 1 to 8 carbon atoms.
  • the hydrocarbon group for R and R may be either linear or branched.
  • Saturated hydrocarbon groups are preferred. Examples thereof include a methyl group, an ethyl group, various propyl groups, various butyl groups, a methoxymethyl group, a methoxyethyl group, and an ethoxyethyl group, and the methyl group is the most common.
  • R and R may be the same or different
  • This ring structure may be a heterocyclic structure in which nitrogen is a heteroatom, or may be a heterocyclic structure in which a nitrogen atom and an oxygen atom are heteroatoms.
  • Examples of the group having a heterocyclic structure include a 1_pyrrolidinyl group, a piperidino group, and a morpholino group.
  • alkoxyamide-based compounds examples include 3-methoxy-1-N, N-dimethylpropionamide, 3_butoxy_N, N-dimethylpropionamide, 3-methoxy-1-N, N-jetylpropionamide, 3 -Ethoxy_N, N-Jetylpropionamide can be cited as S [0019]
  • the number of carbon atoms of R and R is 1 to 4, more preferably R and R.
  • the carbon number of R and R is 1, the carbon number of R is preferably 1 to 8.
  • R has 1 to 6 carbon atoms. This will remove the resist
  • R and R may have 1 to 6 carbon atoms.
  • R has 1 to 3 carbon atoms. This will remove the resist
  • R and R have 2 carbon atoms
  • the alkoxyamide compound represented by the above formula (1) is usually mixed with water and used as a water mixed resist remover.
  • This resist stripper can be handled as a non-hazardous material because it is not flammable by using a water mixture.
  • this resist stripper has high stripping performance even at a high water dilution rate, and can reduce the amount of resist stripper used. Furthermore, even when not using a water mixture, it can be used as a resist remover. Further, since the alkoxyamide compound itself is a third petroleum with a high flash point, safety can be improved.
  • the resist stripper contains about 20 to 100% by weight of the compound represented by the formula (1) and about 0 to 80% by weight of water. More preferably, it contains about 25 to 100% by weight of the compound represented by formula (1) and about 0 to 75% by weight of water, and more preferably about 40 to 100% by weight. A compound represented by the formula (1) and 0 to 60% by weight of water are included. In this way, the stripping performance of the resist stripper can be exhibited well.
  • the addition amount is about 5 to 80% by weight, preferably about 20 to 60% by weight. That is, when the compound represented by the formula (1) is less than about 40% by weight or exceeds about 80% by weight, depending on the compound represented by the formula (1), the peeling performance with respect to the resist is lowered. Because there is a worry to do.
  • the amount of water added is preferably about 0 to 80% by weight, more preferably about 0 to 40% by weight. Good. In this way, if the peeling performance with respect to the resist deteriorates, it is possible to prevent problems.
  • the resist stripper of this embodiment is preferably added with an anticorrosive, a chelating agent, a stripping accelerator, a reducing agent, an oxidizing agent, a surfactant, a buffering agent, Z or an antioxidant, and the like.
  • an anticorrosive e.g., a chelating agent, a stripping accelerator, a reducing agent, an oxidizing agent, a surfactant, a buffering agent, Z or an antioxidant, and the like.
  • Toyole e.g., when a surfactant is added, the permeability to fine gaps is improved, and the peelability of the resist can be improved. Moreover, the performance deterioration by oxidation can be suppressed by adding antioxidant as needed.
  • the above anticorrosives, chelating agents, peeling accelerators, reducing agents, oxidizing agents, surfactants and antioxidants can be used alone or in combination of two or more.
  • anticorrosive or chelating agent examples include aromatic hydroxy compounds, acetylene alcohols, carboxyl group-containing organic compounds and anhydrides, triazole compounds, saccharides, and oxime compounds.
  • aromatic hydroxy compounds examples include aromatic hydroxy compounds, acetylene alcohols, carboxyl group-containing organic compounds and anhydrides, triazole compounds, saccharides, and oxime compounds.
  • triazole compounds examples include triazole compounds, saccharides, and oxime compounds.
  • aromatic hydroxy compound phenol, cresol, xylenol, pyro-power teconole, resorcinol, hydroquinone, pyrogallol, 1,2,4-benzenetriol, salicyl alcohol, p-hydroxybenzyl alcohol, o-hydroxybenzyl alcohol Nore, p-hydroxyphenethyl alcohol, p-aminophenol, m-aminophenol, diaminophenol, aminoresorcinol, ⁇ -hydroxybenzoic acid, o-hydroxybenzoic acid, 2,4-dihydroxybenzoic acid, Examples include 2,5-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, gallic acid, and the like.
  • carboxyl group-containing organic compound and its anhydride formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, oxalic acid, malonic acid, succinic acid, gnoretalic acid, maleic acid, fumaric acid, benzoic acid, phthalic acid, 1,2,3_Benzenetricarboxylic acid, glycolic acid, lactic acid, malic acid, succinic acid, acetic anhydride, phthalic anhydride, maleic anhydride, succinic anhydride, salicylic acid, tartaric acid, acrylic acid, ⁇ -linolenic acid, etc. be able to.
  • Examples of the triazole compound include benzotriazole, ⁇ _tolyltriazole, m-tolyltriazole, p_trinortriazolole, carboxybenzotriazole, 1-hydroxybenzazotriazole, nitrobenzotriazole, dihydroxypropylbenzotriazole, And aminotriazole.
  • saccharide examples include sorbitol, xylitol, palatinit, arabitol, mannitol, sucrose, starch and the like.
  • oxime compounds examples include dimethyl darilioxime and diphenyl daroxime.
  • the above anticorrosive or chelating agent may be used either alone or as a mixture thereof.
  • Examples of the release accelerator include benzenesulfonic acid, toluenesulfonic acid, xylenesulfonic acid, phenolsulfonic acid, or alkylbenzenesulfonic acid such as methyl, propyl, heptyl, octyl, decyl, dodecyl, and the like.
  • the above peeling accelerator may be used either alone or as a mixture thereof.
  • Examples of the reducing agent include hyposulfite, sulfate-based reducing agents, amine-based reducing agents, and other reducing agents.
  • hyposulfite and sulfate-based reducing agent examples include sodium thiosulfate, sodium dithionite, sodium pyrosulfite, and sodium metabisulfite.
  • amine reducing agent examples include hydroxyreamine, monoethanolamine, tryptophan, histidine, methionine, and phenylalanine.
  • reducing agents include ascorbic acid, butynediols, unsaturated ketones, uric acid , Tetraamisole, hydrazines, and derivatives thereof, including strong rubazates, oximes, hydroquinone, pyrogallol, gallic acid, 2,4,5-trihydroxybutyrophenone, tocopheronole, 6-hydroxy -2,5,7,8-tetramethylchroman-2-carboxylic acid, butylated hydroxytoluene (BHT), butylated hydroxybenzene (BHA), 2,6-di-tert-butyl- Four
  • reducing agent may be used either alone or as a mixture thereof.
  • oxidizing agent ozone, hydrogen peroxide, hypochlorous acid or hypochlorite, chlorous acid or chlorite, perchloric acid or perchlorate, hypobromous acid or the following Bromate, bromate or bromate, perbromate or perbromate, hypoiodic acid or hypoiodite, iodic acid or iodate, periodic acid or periodic acid Salt, persulfate or persulfate, peracetic acid or peracetate, perpropionic acid or perpropionate, perbenzoic acid or perbenzoate, tert-ptylnoide oral peroxide, ethylbenzennoide oral peroxide, cumene Examples include Hyde mouth peroxide.
  • the oxidizing agent may be used either alone or as a mixture thereof.
  • surfactant examples include cationic, anionic, nonionic, and fluorine surfactants.
  • Cationic surfactants such as alkyltrimethylammonium salt, alkylamidoamine, alkyldimethylbenzylammonium salt, polyethylenepolyamine cation resin, cetyltrimethylammonium chloride, quaternary ammonium salt, etc.
  • a surfactant may be mentioned.
  • Nonionic surfactants include polyoxyalkylene alkyl ether, polyoxyalkylene alkyl phenyl ether, polyoxyalkylene glycol fatty acid ester, polyoxyalkylene sorbite fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid. Listed are ester-based surfactants.
  • an anionic surfactant a group that exhibits anionic properties in water, A group to be formed (hereinafter referred to as a sulfonic acid group), a group to form a sulfate ester (hereinafter referred to as a sulfate ester group), a group to form a phosphate ester (hereinafter referred to as a phosphate ester group), Examples include groups that form carboxylic acids (hereinafter referred to as carboxylic acid groups).
  • Examples of the compound having a sulfonic acid group include alkyl diphenyl ether disulfonic acid, alkylene disulfonic acid, naphthalene sulfonic acid formalin condensate, phenol sulfonic acid formalin condensate, and phenol phenol sulfonic acid formalin condensate.
  • a compound having two or more anionic functional groups in the child structure a compound such as an alkylbenzene sulfonic acid, a dialkyl succinate sulfonic acid, a monoalkyl succinate sulfonic acid, an alkyl phenoxy succinate sulfonic acid, or a salt thereof. Can be mentioned.
  • Examples of the compound having a sulfate ester group include methyl taurines such as alkyl methyl taurine, acyl methyl taurine, fatty acid methyl taurine, polyoxyalkylene alkyl phenolate ester sulfate sulfate, polyoxyalkylene vinyleno quinoleate ester sulfate ester, Examples thereof include compounds such as polyoxyalkylene polycyclic phenyl ether sulfate, polyoxyalkylene aryl ether sulfate, and salts thereof.
  • Examples of the compound having a phosphoric ester group include compounds such as polyoxyalkylene alkyl ether phosphoric acid and polyoxyalkylene alkyl phenyl ether phosphoric acid, and salts thereof.
  • Examples of the compound having a carboxylic acid group include sarcosine compounds such as isyl sarcosine and fatty acid sarcosine, fatty acid compounds such as coconut oil, oleic acid, acrylic acid and ⁇ -linolenic acid, and salts thereof.
  • compounds having two different anionic functional groups in the molecular structure include compounds such as alkylsulfosuccinic acid and polyoxyalkylenealkylsulfosuccinic acid, which are compounds having a sulfonic acid group and a carboxylic acid group, or salts thereof.
  • fluorosurfactant examples include a perfluoroalkylethylene oxide adduct, a perfluoroalkyl phosphate ester, and a perfluoroalkylphenylglycine.
  • the above surfactants may be used either alone or as a mixture thereof.
  • Examples of the buffer include inorganic acid salts and organic acid salts.
  • organic acids useful in buffer systems include, but are not limited to, formic acid, trifluoroacetic acid, propionic acid, butyric acid, valeric acid, heptanoic acid, lactic acid, oxalic acid, malic acid, malonic acid, succinic acid, fumaric acid, adipine Examples include acids, benzoic acid, phthalic acid and citrate.
  • Conjugate bases useful in the buffer system of the present invention include organic acid salts, ammonia, tetramethylammonium hydroxide, tetraalkylammonium hydroxide, 2_ (methylamino) ethanol, monoisopropanol.
  • the salt is at least one selected from the group consisting of carboxylate, sulfate, sulfonate, phosphonate, nitrate, hydrochloride and borate. Specifically, ammonium acetate, ammonium citrate, ammonium oxalate, ammonium sulfosuccinate, ammonium sulfate, ammonium methanesulfonate, ammonium phosphonate, ammonium nitrate, ammonium chloride, ammonium tetraborate, ammonium acrylic acid, etc. Is mentioned. Paying attention to cations, in addition to ammonium salt, amin salt or quaternary ammonium salt may be used.
  • amines examples include hydroxylamines such as hydroxylamine, jetylhydroxylamine, anolamines such as ethylamine, propanediamine, dibutylamine, and trimethylamine, monoethanolamine, methylethanolamine, and methyljetanolamine.
  • Alkanolamines such as triethanolamine, monoisopropanolamine, diglycolamine, N, N-dimethyl-1-2- (2-aminoethoxy) ethanol, aromatic amines such as aniline and benzylamine, Morpholines such as ethylmorpholine, hydroxymorpholine, aminopropylone morpholine, 1 _ (2-aminoethyl) piperidine, 1 _ (2 _ Hydroxyethyl) piperazine, 1- (2 aminoethyl) piperazine, 1 (3-aminoprohi.
  • Alkanolamines such as triethanolamine, monoisopropanolamine, diglycolamine, N, N-dimethyl-1-2- (2-aminoethoxy) ethanol, aromatic amines such as aniline and benzylamine, Morpholines such as ethylmorpholine, hydroxymorpholine, aminopropylone morpholine, 1 _ (2-aminoethyl
  • Nore mono-imita, Norole, 1,8-diazabi'cyclo [5.4.0] undec-7 -ene, NN N '-trimethylaminoethanolamine, pentamethyljetylenetriamine and the like.
  • the amine is not particularly limited as long as it exhibits basicity.
  • quaternary ammonium ions that form quaternary ammonium salts include tetramethyl ammonium ion, tetraethyl ammonium ion, triethyl methyl ammonium ion, lauryl trimethyl ammonium ion, and benzyl trimethyl ammonium ion.
  • the above buffering agents may be used either alone or as a mixture thereof.
  • examples thereof include bisphenol compounds such as phenol), 4,4, -methylenebis (2,6 di-tert-butylphenol), 4,4'-butylidenebis (3-methyl-6-tertbutylphenol), and the like.
  • phosphite antioxidants such as triphenyl phosphate, trisnoylphenyl phosphite and tris (mono and di-noylphenyl) phosphate can be mentioned.
  • sulfur-based antioxidants such as dilauryl dipropionate and distearyl thiodipropionate can be mentioned.
  • the above antioxidants may be used either alone or as a mixture thereof. Also acid
  • the amount of antioxidation agent used is preferably about 0.01 to 1.0% by weight based on the resist stripper.
  • the resist remover that is effective in the present embodiment uses the alkoxyamide-based compound represented by the formula (1), so that it has high peeling performance and is anticorrosive against copper, aluminum, and the like. It is very excellent in sex.
  • a water-based release agent it is flammable and safe, and since it has water solubility, it can be rinsed with water and does not require an IPA rinse, thus improving productivity. be able to.
  • FIG. 1 shows Table 1 showing the release agent type (composition of the release solution), release performance, and anticorrosion performance for Examples 1 to 15.
  • FIG. 2 shows Table 2 showing the release agent type (the composition of the release solution), the release performance and the anticorrosion performance for Comparative Examples:!
  • Substrate A film-forming glass (size: about 100 mm X 100 mm) manufactured by Hitachi Metals, Ltd. was used.
  • HPR204 naphthoquinone diazide / Novolac resin
  • Fuji Film Electronics Materials Co., Ltd. was applied and baked in an oven at a predetermined temperature for about 15 minutes. That is, Examples 1, 2, 3, 5-8, 10-: 15 and Comparative Examples 1, 3-6 were baked in an oven at about 130 ° C. for about 15 minutes. In Examples 4 and 9, and Comparative Example 2, those baked in an oven at about 150 ° C. for about 15 minutes were used.
  • ⁇ It takes less than 40 seconds to become transparent.
  • the predetermined temperature when stirring is room temperature (for example, 0-30 ° C). , Usually 20-25 ° C).
  • the predetermined temperature during stirring was set to about 40 ° C.
  • Resist stripping—2 About 5 ml of the stripping agent and the above-prepared resist substrate test piece are placed in a sample bottle of about 30 ml and stirred for about 60se C at a predetermined temperature. Then, the resist substrate was taken out and immediately rinsed with acetone, and then the surface after drying at about 50 ° C. for about 30 minutes was observed and judged as follows.
  • ⁇ There is no cloudy portion on the glass substrate surface, and the resist is completely washed and peeled off.
  • ⁇ The glass substrate surface has a slightly cloudy portion, and the resist is almost removed by washing.
  • the predetermined temperature for stirring for about 60 seconds is the room temperature (for example, 0-30 °). C, usually 20-25 ° C). In Examples 4 and 9, and Comparative Example 2, the predetermined temperature when stirring for about 60 seconds was about 40 ° C.
  • the anticorrosion performance was evaluated by the following two evaluation methods.
  • Anticorrosion-1 Put a release agent in a sample bottle of about 30ml, immerse a copper wire of about 0.5mm in diameter about 100mm in diameter, and observe the degree of coloration after 1 week. It was judged.
  • ⁇ No discoloration at all. ⁇ : Slightly discolored to light blue.
  • Anti-corrosion—2 Make a Mo (molybdenum) / Al / Mo multilayer wiring board, put this test piece (about 10mm x 5mm) into a sample bottle of about 30ml, add about 5ml of release agent, and add about 40 ° Soaked in C for about 5 minutes. Immersion 'After the corrosion operation, observation was made according to the following procedure, and judgment was made as follows.
  • step 1 perform IPA rinse, as step 2, perform acetone rinse, and as step 3, dry at approximately 50 ° C for approximately 30 minutes, and then use SEM (scanning electron microscope) to determine the degree of corrosion of A1. Was observed.
  • SEM scanning electron microscope
  • a resist release agent comprising about 80% by weight of 3-methoxy-N, N dimethylpropionamide (abbreviated as MDMPA as appropriate) and about 20% by weight of water. Prepared. Subsequently, the peeling test and the corrosion test were performed.
  • Resist stripping property-1 ⁇ (Time until the substrate became transparent was 38 seconds.)
  • Resist stripping property 2 :
  • a resist release agent comprising about 60% by weight of 3-methoxy-N, N-dimethylpropionamide and about 40% by weight of water was prepared. Subsequently, the above peeling test and corrosion test were conducted.
  • Resist strippability-1 ⁇ (Time until substrate became transparent was 39 seconds.)
  • Resist strippability 2 Anticorrosion 1: 0
  • This resist stripper has a slightly cloudy portion on the glass substrate surface in resist stripping property 2, and the resist is almost cleaned and stripped (a small amount of resist residue is observed). In addition, this resist stripper was excellent in stripping performance and corrosion resistance in other tests.
  • a release agent according to Example 3 a resist release agent comprising about 100% by weight of 3-methoxy-N, N dimethylpropionamide was prepared. Subsequently, the above peeling test and corrosion test were conducted.
  • Resist stripping property-1 ⁇ (Time until the substrate became transparent was 32 seconds.)
  • Resist stripping property 2 :
  • a release agent according to Example 4 a resist release agent composed of about 100% by weight of 3 methoxy-N, N-dimethylpropionamide was prepared. Subsequently, the above peeling test and corrosion test were conducted.
  • Resist stripping property-1 ⁇ (Time until the substrate becomes transparent was 35 seconds.)
  • Resist stripping property 2 ⁇
  • a release agent according to Example 5 about 100% by weight of 3_butoxy-N, N-dimethylpropylene was used. A resist stripper made of lopionamide (abbreviated as BDMPA as appropriate) was prepared. Subsequently, the above peeling test and corrosion test were conducted.
  • BDMPA lopionamide
  • Resist releasability _ 1 ⁇ (Time until substrate became transparent was 31 seconds.)
  • Resist releasability — 2 ⁇
  • This resist stripper has a slightly cloudy portion on the surface of the glass substrate in resist stripping property-2, and the resist is almost cleaned and stripped (a small amount of resist residue is recognized). In addition, this resist stripper was excellent in stripping performance and corrosion resistance in other tests.
  • a release agent according to Example 6 a resist release agent comprising about 80 wt% of 3 butoxy-N, N dimethylpropionamide and about 20 wt% of water was prepared. Subsequently, the above peeling test and corrosion test were conducted.
  • Resist releasability _ 1 ⁇ (The time until the substrate became transparent was 24 seconds.)
  • Resist releasability — 2 ⁇
  • This resist stripper has a slightly cloudy portion on the surface of the glass substrate in resist stripping property-2, and the resist is almost cleaned and stripped (a small amount of resist residue is recognized). In addition, this resist stripper was excellent in stripping performance and corrosion resistance in other tests.
  • a release agent according to Example 7 a resist release agent comprising about 60% by weight of 3 butoxy-N, N dimethylpropionamide and about 40% by weight of water was prepared. Subsequently, the above peeling test and corrosion test were conducted. The test results are shown in Table 1.
  • Resist strippability-1 (Time until the substrate became transparent was 29 seconds.)
  • Resist stripp 2 (Time until the substrate became transparent was 29 seconds.)
  • a resist release agent comprising about 40% by weight of 3 butoxy-N, N dimethylpropionamide and about 60% by weight of water was prepared. Subsequently, the above peeling test and corrosion test were conducted.
  • Resist strippability-1 (Time until the substrate became transparent was 24 seconds.)
  • Resist stripp 2 (Time until the substrate became transparent was 24 seconds.)
  • a resist release agent comprising about 60% by weight of 3_butoxy-N, N-dimethylpropionamide and about 40% by weight of water was prepared. Subsequently, the above peeling test and corrosion test were conducted.
  • Resist strippability-1 ⁇ (Time until substrate became transparent was 39 seconds.)
  • Resist strippability 2 :
  • This resist stripper has a slightly cloudy portion on the glass substrate surface in resist stripping property 2, and the resist is almost cleaned and stripped (a small amount of resist residue is observed). In addition, this resist stripper is used in other tests for stripping performance and corrosion resistance. It was excellent.
  • a resist release agent comprising about 100% by weight of 3-methoxy-N, N-jetinorepropionamide (abbreviated as MDEPA as appropriate) was prepared. Subsequently, the peeling test and the corrosion test were performed.
  • MDEPA 3-methoxy-N, N-jetinorepropionamide
  • Resist stripping property-1 ⁇ (Time until the substrate becomes transparent was 30 seconds.)
  • Resist stripping property 2 :
  • a resist remover comprising about 80% by weight of 3-methoxy-1-N, N-jetylpropionamide and about 20% by weight of water was prepared as a remover useful for Example 11. Subsequently, the above peeling test and corrosion test were conducted.
  • Resist releasability _ 1 0 (Time until the substrate became transparent was 18 seconds.)
  • Resist releasability — 2 0 (Time until the substrate became transparent was 18 seconds.)
  • a resist stripping agent according to Example 12 a resist stripping agent comprising about 60% by weight of 3-methoxy-N, N-jetylpropionamide and about 40% by weight of water was prepared. Subsequently, the above peeling test and corrosion test were conducted.
  • Resist releasability _ 1 0 (Time until the substrate became transparent was 28 seconds.)
  • Resist releasability — 2 0
  • Anticorrosion 1 0
  • a resist stripping agent comprising about 100% by weight of 3 ethoxy N, N jetyl propionamide (abbreviated as EDEPA as appropriate) was prepared. Subsequently, the above peeling test and corrosion test were conducted.
  • EDEPA N jetyl propionamide
  • Resist stripping property-1 ⁇ (Time until the substrate became transparent was 19 seconds.)
  • Resist stripping property 2 :
  • This resist stripper has a slightly cloudy portion on the glass substrate surface in resist stripping property 2, and the resist is almost cleaned and stripped (a small amount of resist residue is observed). In addition, this resist stripper was excellent in stripping performance and corrosion resistance in other tests.
  • a resist stripping agent according to Example 14 a resist stripping agent comprising about 80% by weight of 3_ethoxy_N, N-jetylpropionamide and about 20% by weight of water was prepared. Subsequently, the above peeling test and corrosion test were conducted.
  • Resist stripping property-1 ⁇ (Time until the substrate became transparent was 19 seconds.)
  • Resist stripping property 2 :
  • Resist releasability _ 1 ⁇ (The time until the substrate became transparent was 29 seconds.)
  • Resist releasability — 2 ⁇
  • This resist stripper has a slightly cloudy portion on the surface of the glass substrate in resist stripping property-2, and the resist is almost cleaned and stripped (a small amount of resist residue is recognized). In addition, this resist stripper was excellent in stripping performance and corrosion resistance in other tests.
  • Resist releasability _ 1 X (Time until the substrate became transparent was 45 seconds.)
  • Resist releasability — 2 ⁇
  • This resist stripper required a long time for stripping in the resist stripping_1, and a small amount of resist residue was observed in the resist stripping_2. In addition, this resist stripper turned slightly light blue in anticorrosion property_1, and further, A1 eluted slightly in anticorrosion property_2, and corrosion was observed.
  • Resist stripping property-1 X (Time until the substrate became transparent was 50 seconds.)
  • Resist stripping property 2 :
  • This resist stripper required a long time for stripping in the resist stripping_1, and a small amount of resist residue was observed in the resist stripping_2. In addition, this resist stripper turned slightly light blue in anticorrosion property_1, and further, A1 eluted slightly in anticorrosion property_2, and corrosion was observed.
  • Resist strippability-1 X (Time until the substrate became transparent was 56 seconds.)
  • Resist strippability-2 X
  • This resist stripper requires a long time for stripping in resist stripping_1, and in resist stripping_2, more than half of the surface of the glass substrate is cloudy, and cleaning stripping is insufficient. The resist remained. In addition, this resist stripper turned slightly light blue in the anticorrosion property_1, and further, in the anticorrosion property_2, A1 was slightly eluted and corrosion was observed.
  • Resist strippability-1 ⁇ (Time to clear the substrate was 38 seconds.)
  • Resist strippability 2 ⁇
  • resist stripper had excellent strippability in resist strippability-1, a small amount of resist residue was observed in resist strippability_2. In addition, this resist stripper clearly turned blue in anticorrosion property 1 and, further, in the anticorrosion property 2, A1 was clearly eluted and severe corrosion was observed.
  • Resist strippability-1 (Time until the substrate became transparent was 24 seconds.)
  • Resist stripp 2 (Time until the substrate became transparent was 24 seconds.)
  • This resist remover was excellent in peelability.
  • this resist stripper clearly turned blue in the anticorrosion property_1, and further, in the anticorrosion property_2, A1 was clearly eluted and severe corrosion was observed.
  • Resist strippability-1 ⁇ (Time until the substrate became transparent was 29 seconds.)
  • Resist strippability 2 :
  • Anticorrosive 1 X
  • Anticorrosion 2 X
  • resist stripper was excellent in stripping property in resist stripping property 1, a small amount of resist residue was observed in resist stripping property 2. In addition, this resist stripper clearly turned blue in anticorrosion property 1 and, further, in the anticorrosion property 2, A1 was clearly eluted and severe corrosion was observed.
  • resist stripper of the present invention has been described with reference to the preferred embodiment, the resist stripper according to the present invention is not limited to the above-described embodiment. Needless to say, it is possible to implement this change.
  • the compound represented by the formula (1) contained in the resist stripper is not limited to one type, for example, a resist stripper containing two or more compounds represented by the formula (1). There may be.
  • liquid crystal / semiconductor resist removers are not limited to liquid crystal / semiconductor resist removers.
  • print board removers for example, print board removers, resist developers, flux cleaners, resin solvents (for example, polyimide resin solvents, polyamides) It is also used as a solvent for resins.
  • resin solvents for example, polyimide resin solvents, polyamides

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Abstract

L'invention concerne un agent de décapage de resist présentant d'excellentes propriétés de décapage. Cet agent n'est pas inflammable, et par conséquent il est sûr. Il ne provoque pas de corrosion d'une matière conductrice et par conséquent présente d'excellentes propriétés anticorrosion. Cet agent de décapage de résiste comprend un composé de formule (1). Dans cette formule, R3 désigne un groupe alkyle présentant 1 à 18 atomes de carbone, et R1 et R2 désignent indépendamment un atome d'hydrogène ou un groupe d'hydrocarbures présentant un à six atomes de carbone qui peuvent présenter une liaison éther.
PCT/JP2007/061867 2006-06-21 2007-06-13 Agent de décapage de resist WO2007148574A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008015218A (ja) * 2006-07-06 2008-01-24 Idemitsu Kosan Co Ltd レブリン酸アミド類を用いたレジスト剥離剤、溶剤、洗浄剤
JP2009249297A (ja) * 2008-04-02 2009-10-29 Idemitsu Kosan Co Ltd Ｎ，ｎ−ジメチルプロピオンアミド化合物及びその製造方法、並びにそれを用いたレジスト剥離剤
WO2010090146A1 (fr) * 2009-02-03 2010-08-12 出光興産株式会社 Composition de décapage de résist et procédé de décapage de résist utilisant celle-ci
WO2011012562A2 (fr) 2009-07-31 2011-02-03 Basf Se Composition liquide contenant un pesticide, un tensioactif non ionique et un amide propionique
WO2018088511A1 (fr) * 2016-11-11 2018-05-17 株式会社カネコ化学 Agent de démoulage pour article durci de résine durcissable, agent lubrifiant pour article durci de résine durcissable, et agent de réduction de volume pour mousse durcie de résine durcissable

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JPH02981A (ja) * 1988-02-25 1990-01-05 Hoya Corp 感光性樹脂用剥離液及びこれを用いる感光性樹脂の剥離方法
JP2000199972A (ja) * 1998-08-05 2000-07-18 Samsung Electronics Co Ltd アルコキシｎ―ヒドロキシアルキルアルカンアミドからなるレジスト除去剤、レジスト除去用組成物、これらの製造方法及びこれらを用いたレジスト除去方法
JP2001152190A (ja) * 1999-11-26 2001-06-05 Samsung Electronics Co Ltd レジスト除去用組成物及びこれを用いたレジスト除去方法
JP2003098691A (ja) * 2001-08-17 2003-04-04 Samsung Electronics Co Ltd レジスト除去用組成物及びこれを利用したレジスト除去方法
JP2005047885A (ja) * 2003-07-17 2005-02-24 Idemitsu Kosan Co Ltd β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法

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Publication number Priority date Publication date Assignee Title
JPH02981A (ja) * 1988-02-25 1990-01-05 Hoya Corp 感光性樹脂用剥離液及びこれを用いる感光性樹脂の剥離方法
JP2000199972A (ja) * 1998-08-05 2000-07-18 Samsung Electronics Co Ltd アルコキシｎ―ヒドロキシアルキルアルカンアミドからなるレジスト除去剤、レジスト除去用組成物、これらの製造方法及びこれらを用いたレジスト除去方法
JP2001152190A (ja) * 1999-11-26 2001-06-05 Samsung Electronics Co Ltd レジスト除去用組成物及びこれを用いたレジスト除去方法
JP2003098691A (ja) * 2001-08-17 2003-04-04 Samsung Electronics Co Ltd レジスト除去用組成物及びこれを利用したレジスト除去方法
JP2005047885A (ja) * 2003-07-17 2005-02-24 Idemitsu Kosan Co Ltd β−アルコキシプロピオンアミド類、溶剤、洗浄剤および液状薬剤組成物、並びにβ−アルコキシプロピオンアミド類の製造方法

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008015218A (ja) * 2006-07-06 2008-01-24 Idemitsu Kosan Co Ltd レブリン酸アミド類を用いたレジスト剥離剤、溶剤、洗浄剤
JP2009249297A (ja) * 2008-04-02 2009-10-29 Idemitsu Kosan Co Ltd Ｎ，ｎ−ジメチルプロピオンアミド化合物及びその製造方法、並びにそれを用いたレジスト剥離剤
WO2010090146A1 (fr) * 2009-02-03 2010-08-12 出光興産株式会社 Composition de décapage de résist et procédé de décapage de résist utilisant celle-ci
US20110287995A1 (en) * 2009-02-03 2011-11-24 Idemitsu Kosan Co., Ltd. Resist remover composition and method for removing resist using same
JP5238043B2 (ja) * 2009-02-03 2013-07-17 出光興産株式会社 レジスト剥離剤組成物及びそれを用いたレジスト剥離方法
US8563495B2 (en) 2009-02-03 2013-10-22 Idemitsu Kosan Co., Ltd. Resist remover composition and method for removing resist using same
TWI452446B (zh) * 2009-02-03 2014-09-11 Idemitsu Kosan Co A photoresist stripping agent composition and a method of peeling using the same
CN102301283B (zh) * 2009-02-03 2014-10-08 出光兴产株式会社 抗蚀剂剥离剂组合物以及使用该组合物的抗蚀剂剥离方法
KR101487853B1 (ko) * 2009-02-03 2015-01-29 이데미쓰 고산 가부시키가이샤 레지스트 박리제 조성물 및 그것을 이용한 레지스트 박리 방법
WO2011012562A2 (fr) 2009-07-31 2011-02-03 Basf Se Composition liquide contenant un pesticide, un tensioactif non ionique et un amide propionique
WO2018088511A1 (fr) * 2016-11-11 2018-05-17 株式会社カネコ化学 Agent de démoulage pour article durci de résine durcissable, agent lubrifiant pour article durci de résine durcissable, et agent de réduction de volume pour mousse durcie de résine durcissable
JPWO2018088511A1 (ja) * 2016-11-11 2018-11-08 株式会社カネコ化学 硬化性樹脂の硬化物の剥離剤、硬化性樹脂の硬化物の膨潤剤及び硬化性樹脂の硬化フォームの減容剤

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