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WO2010086893A1 - Agent de nettoyage pour semi-conducteur à câblage de cuivre - Google Patents

Agent de nettoyage pour semi-conducteur à câblage de cuivre Download PDF

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Publication number
WO2010086893A1
WO2010086893A1 PCT/JP2009/000294 JP2009000294W WO2010086893A1 WO 2010086893 A1 WO2010086893 A1 WO 2010086893A1 JP 2009000294 W JP2009000294 W JP 2009000294W WO 2010086893 A1 WO2010086893 A1 WO 2010086893A1
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WIPO (PCT)
Prior art keywords
cleaning agent
copper wiring
hydroxyl group
copper
acid
Prior art date
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Ceased
Application number
PCT/JP2009/000294
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English (en)
Japanese (ja)
Inventor
中西睦
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Sanyo Chemical Industries Ltd
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Sanyo Chemical Industries Ltd
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Priority to PCT/JP2009/000294 priority Critical patent/WO2010086893A1/fr
Publication of WO2010086893A1 publication Critical patent/WO2010086893A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/265—Carboxylic acids or salts thereof
    • 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
    • C11D7/3209—Amines or imines with one to four nitrogen atoms; Quaternized amines
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
    • C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
    • C23G1/10—Other heavy metals
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
    • C23G1/24—Cleaning or pickling metallic material with solutions or molten salts with neutral solutions
    • C23G1/26—Cleaning or pickling metallic material with solutions or molten salts with neutral solutions using inhibitors
    • H10P70/277—
    • 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 cleaning agent for a copper wiring semiconductor.
  • Patent Document 1 tetraalkylammonium hydroxide as a cleaning agent for copper wiring semiconductors, which removes particles (such as inorganic fine particles of abrasives) adhering to the copper wiring in the polishing process and suppresses corrosion of the copper wiring
  • Cleaning agents containing effective amounts of corrosion inhibitors benzotriazole, gallic acid, etc.
  • complexing agents acetone oxime, alanine, etc.
  • the organic residue derived from the abrasive is an insoluble complex composed of an antirust agent and copper ions, and examples of the main antirust agent include benzotriazole and quinaldic acid (Patent Document 3). JP 2003-536258 A JP 2008-528762 A JP 2003-168660 A
  • the present invention provides a removal performance (removal rate and removal rate) of organic residues (benzotriazole and quinaldic acid) derived from the polishing process, a copper wiring corrosion inhibition effect (a copper elution amount as a copper corrosion inhibition performance, and an insulating film)
  • An object of the present invention is to provide a cleaning agent for a copper wiring semiconductor excellent in removal of metals such as zinc remaining thereon.
  • the present invention relates to an organic amine (A), a quaternary ammonium compound (B), at least one polyvalent hydroxyl group-containing compound (C) selected from the group consisting of the following (C1) to (C4), hydroxytricarboxylic acid
  • C1 Polyhydric hydroxyl group-containing aliphatic hydrocarbon or polyhydric hydroxyl group-containing alicyclic hydrocarbon
  • C2 Polyhydric hydroxyl group-containing aliphatic hydrocarbon in which the methylene group in the molecular chain is substituted only with an ether group Hydroxyl group-containing alicyclic hydrocarbon
  • C3 polyvinyl alcohols
  • C4 saccharides
  • the cleaning agent for copper wiring semiconductors of the present invention is excellent in removal of organic residues derived from abrasives and removal of metal residues on the insulating film, and is excellent in copper corrosion inhibition performance of copper wiring.
  • a semiconductor substrate or semiconductor element of the present invention a semiconductor substrate or semiconductor element having excellent contact resistance and no short circuit of wiring can be easily obtained.
  • the cleaning agent for copper wiring semiconductor according to the present invention comprises organic amine (A), quaternary ammonium compound (B), polyvalent hydroxyl group-containing compound (C), specific hydroxycarboxylic acid (D) and water (W) as essential components.
  • the hydroxycarboxylic acid (D) is hydroxytricarboxylic acid (D1), hydroxytetracarboxylic acid (D2), or a combination thereof.
  • organic amine (A) examples include aliphatic amine (A1) and cyclic amine (A2).
  • the aliphatic amine (A1) includes an alkylamine (A11) having 1 to 6 carbon atoms (hereinafter abbreviated as C), an alkanolamine (A12) having 2 to 6 carbon atoms, an alkylenediamine (A13) having 2 to 5 carbon atoms, and an amino group. And 3 to 6 polyamines (A14).
  • C1-6 alkylamines (A11) include methylamine, ethylamine, propylamine, isopropylamine, hexylamine and other monoalkylamines; dimethylamine, ethylmethylamine, propylmethylamine, butylmethylamine, diethylamine, propylethylamine And dialkylamines such as diisopropylamine; and trialkylamines such as trimethylamine, ethyldimethylamine, diethylmethylamine, triethylamine, tri-n-propylamine, and tri-n-butylamine.
  • Examples of the C2-6 alkanolamine (A12) include monoethanolamine, diethanolamine, triethanolamine, dimethylaminoethanol, diethylaminoethanol, 2-amino-2-methyl-1-propanol, N- (aminoethyl) ethanolamine, N, N-dimethyl-2-aminoethanol, 2- (2-aminoethylaminoethanol) and the like can be mentioned.
  • Examples of the C2-5 alkylene diamine (A13) include 1,2-diaminoethane, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, 1,6-diaminohexane, and the like. .
  • the polyamine (A14) having 3 to 6 amino groups is a polyamine in which a C2-6 alkylene chain is sandwiched between two amino groups, and includes triethylenetetramine, tetraethylenepentamine, and hexaethylenepentane. And amine, iminobispropylamine, bis (hexamethylene) triamine, and pentaethylenehexamine.
  • Examples of the cyclic amine (A2) include an aromatic amine (A21), an alicyclic amine (A22), and a heterocyclic amine (A23).
  • aromatic amine (A21) examples include aniline, 1,3-phenylenediamine, 2,4-tolylenediamine, 1,3-xylylenediamine, 1,5-naphthalenediamine, 2,3-anthracenediamine, and the like. It is done.
  • Examples of the alicyclic amine (A22) include isophorone diamine and 1,2-cyclohexane diamine.
  • heterocyclic amine (A23) examples include piperazine, N-aminoethylpiperazine, 1,4-diaminoethylpiperazine, and the like.
  • organic amines (A) an aliphatic amine (A1) is preferable from the viewpoint of water solubility, and a C2-6 alkanolamine (A12) is more preferable from the viewpoint of organic residue removal performance.
  • a C2-6 alkanolamine (A12) is more preferable from the viewpoint of organic residue removal performance.
  • monoethanolamine and triethanolamine are preferred. Particularly preferred is monoethanolamine.
  • organic amine (A) is organic amine (A), quaternary ammonium compound (B), polyvalent hydroxyl group-containing compound (C), hydroxycarboxylic acid (D) and Based on the total weight of water (W), it is usually 0.001 to 5% by weight, preferably 0.005 to 3% by weight, more preferably 0.01 to 2% by weight, particularly preferably 0.01 to 2% by weight. 1% by weight.
  • Examples of the quaternary ammonium compound (B) include tetraalkylammonium salts, trialkyl-hydroxyalkylammonium salts, dialkyl-bis (hydroxyalkyl) ammonium salts, and tris (hydroxyalkyl) alkylammonium salts.
  • quaternary ammonium compounds (B) from the viewpoint of detergency, tetraalkylammonium hydroxide, (hydroxyalkyl) trialkylammonium hydroxide, bis (hydroxyalkyl) dialkylammonium hydroxide and tris (hydroxyalkyl) alkyl Ammonium hydroxide is preferred.
  • tetraalkylammonium hydroxide and (hydroxyalkyl) trialkylammonium hydroxide are preferred from the viewpoint of copper corrosion inhibition, more preferably tetramethylammonium hydroxide, tetraethylammonium hydroxide, (hydroxyethyl) trimethylammonium hydroxide ( Choline) is preferred, and tetramethylammonium hydroxide and (hydroxyethyl) trimethylammonium hydroxide are particularly preferred.
  • the content of the quaternary ammonium compound (B) is organic amine (A), quaternary ammonium compound (B), polyhydric hydroxyl group-containing compound (C), hydroxycarboxylic acid (D) from the viewpoint of detergency and copper corrosion inhibition. ) And water (W), usually 0.01 to 10% by weight, preferably 0.02 to 5% by weight, more preferably 0.05 to 2% by weight.
  • the polyvalent hydroxyl group-containing compound (C) is a compound containing two or more hydroxyl groups, and is at least one compound selected from the group consisting of the following (C1) to (C4).
  • C1 Polyhydric hydroxyl group-containing aliphatic hydrocarbon or polyhydric hydroxyl group-containing alicyclic hydrocarbon
  • C2 Polyhydric hydroxyl group-containing aliphatic hydrocarbon in which the methylene group in the molecular chain is substituted only with an ether group
  • the hydroxyl group-containing alicyclic hydrocarbon (C3): polyvinyl alcohols (C4): saccharides (C1) to (C4) will be described in further detail.
  • Examples of the polyvalent hydroxyl group-containing aliphatic hydrocarbon or polyvalent hydroxyl group-containing alicyclic hydrocarbon (C1) include polyvalent hydroxyl group-containing aliphatic hydrocarbon (C1a) and polyvalent hydroxyl group-containing alicyclic hydrocarbon (C1b). .
  • the hydrocarbon group portion may be linear or branched, and may be a saturated hydrocarbon group or an unsaturated hydrocarbon group. Is mentioned. Specific examples include the following compounds depending on the number of hydroxyl groups.
  • C1a1 Polyhydric hydroxyl group-containing aliphatic hydrocarbon containing two hydroxyl groups, specifically C2-13 alkylene glycols such as ethylene glycol, 1,2-propanediol, 1,3-butanediol, 2- Examples include butene-1,4-diol, 1-pentene-3,5-diol, 3-hexene-2,5-diol, and the like.
  • (C1a2) Polyhydric hydroxyl group-containing aliphatic hydrocarbons containing three hydroxyl groups, for example 1,2,3-propanetriol, 1,2,5-pentanetriol, 2,3,4-pentanetriol, 1,2,6 -Hexanetriol, 1,2,3-octanetriol, trimethylolpropane, 2,4-dimethyl-1,3,5-pentanetriol, 3-ethyl-2,4-dimethylpentane-2,3,4-triol 1,3,5-trihydroxy-3-methylpentane and the like.
  • (C1a3) Polyhydric hydroxyl group-containing aliphatic hydrocarbons containing 4 or more hydroxyl groups such as erythritol, threitol, butanetetraol, 1,1,5,5-pentanetetraol, 1,2,5,6-hexane Examples include tetraol, 1,2,6,7-heptanetetraol, D-sorbitol, xylitol and the like.
  • Examples of the polyvalent hydroxyl group-containing alicyclic hydrocarbon (C1b) include the following compounds depending on the number of hydroxyl groups contained in the molecule.
  • (C1b1) Polyhydric hydroxyl group-containing alicyclic hydrocarbon containing two hydroxyl groups Examples include 1,4-cyclohexanediol, 1,3-cyclohexanediol, 1,2-cycloheptanediol, and the like.
  • C1b2 Polyhydric hydroxyl group-containing alicyclic hydrocarbons containing 3 or more hydroxyl groups such as 1,3,5-cyclohexanetriol, 1,2,3-cyclohexanetriol, 1,2,3,5-cyclohexanetetraol , Inositol, cyclopentanepentaol, and the like.
  • (C1a) is preferable from the viewpoint of stability and solubility, and from the viewpoint of organic residue removal of the cleaning agent for copper wiring semiconductors, a polyhydric hydroxyl group-containing aliphatic group containing 4 or more hydroxyl groups. Hydrocarbon (C1a3) is preferred, and D-sorbitol is particularly preferred.
  • polyhydric hydroxyl group-containing aliphatic hydrocarbons or polyhydric hydroxyl group-containing alicyclic hydrocarbons (C2) in which the methylene group in the molecular chain is substituted only with an ether group the methylene group in the molecular chain is substituted only with an ether group
  • polyhydric hydroxyl group-containing alicyclic hydrocarbons (C2b) in which the methylene group in the molecular chain is substituted only with ether groups are examples of polyhydric hydroxyl group-containing aliphatic hydrocarbons or polyhydric hydroxyl group-containing alicyclic hydrocarbons (C2) in which the methylene group in the molecular chain is substituted only with an ether group
  • polyhydric hydroxyl group-containing alicyclic hydrocarbons (C2b) in which the methylene group in the molecular chain is substituted only with ether groups the polyhydric hydroxyl group-containing aliphatic hydrocarbons or polyhydric hydroxyl group-containing
  • the hydrocarbon group portion may be linear or branched, and may be a saturated hydrocarbon group or an unsaturated hydrocarbon group. Depending on the number of hydroxyl groups contained in the molecule, the following (C2a1) And (C2a2).
  • (C2a1) A polyhydric hydroxyl group-containing aliphatic hydrocarbon in which the methylene group in the molecular chain is substituted only with an ether group and contains two hydroxyl groups, such as diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, glycerin monomethyl ether, glycerin And monoethyl ether.
  • (C2a2) Polyhydric hydroxyl group-containing aliphatic hydrocarbon in which the methylene group in the molecular chain is substituted only with an ether group and contains 3 or more hydroxyl groups, for example, bispentaerythritol, tripentaerythritol, 5- (hydroxymethyl) -4 -Oxahexane-1,2,6-triol and the like.
  • Examples of (C2b) include alicyclic hydrocarbons having two or more hydroxyl groups in the molecular chain and having the methylene group in the molecular chain substituted with an ether group, such as ethylene oxide of 1,4-cyclohexanediol.
  • (C2a) is preferred from the viewpoint of solubility in water (W).
  • (C2a1) is preferable from the viewpoint of detergency, more preferably diethylene glycol, triethylene glycol, tetraethylene glycol, and particularly preferably triethylene glycol.
  • Polyvinyl alcohols (C3) include polyvinyl alcohol having a saponification degree of 58% or more, modified polyvinyl alcohol having a modification rate of 50% or less (sulfonic acid group modification, cation modification, cyanoethyl group modification, silanol group modification, terminal thiol modification) , Nonionic group-modified polyvinyl alcohol) and the like.
  • the degree of saponification is 58% or more, the molecule may have an ester group derived from polyvinyl acetate.
  • polyvinyl alcohol sulfonic acid-modified polyvinyl alcohol, and cation-modified polyvinyl alcohol are preferable from the viewpoint of detergency, and polyvinyl alcohol is preferable from the viewpoint of copper corrosion inhibition effect, and particularly preferably, the degree of saponification is 80. % Of polyvinyl alcohol.
  • the weight average molecular weight of (C3) is usually from 1,000 to less than 1,000,000 from the viewpoint of detergency and solubility, and from the viewpoint of detergency, the weight average molecular weight is from 5,000 to 500,000.
  • the weight average molecular weight is 5,000 or more and less than 300,000, and the weight average molecular weight is 5,000 or more and less than 100,000.
  • saccharides As saccharides (C4), monosaccharides, polysaccharides (C4a); and some of them are substituted with hydrogen groups, carbonyl groups, carboxyl groups, formyl groups, sulfonyl groups, ether groups, amide groups, amino groups, or phosphono groups.
  • Sugar derivative (C4b) As saccharides (C4), monosaccharides, polysaccharides (C4a); and some of them are substituted with hydrogen groups, carbonyl groups, carboxyl groups, formyl groups, sulfonyl groups, ether groups, amide groups, amino groups, or phosphono groups.
  • Sugar derivative (C4b) As saccharides (C4), monosaccharides, polysaccharides (C4a); and some of them are substituted with hydrogen groups, carbonyl groups, carboxyl groups, formyl groups, sulfonyl groups, ether groups, amide groups, amino groups, or phosphono groups.
  • C4a Monosaccharides and polysaccharides such as D-glucose, D-galactose, sucrose, D-(+)-trehalose, lactose, D-raffinose, fructooligosaccharide, galactooligosaccharide, starch, amylose and dextrin.
  • (C4b) sugar derivatives such as glucuronic acid, gluconic acid, glucaric acid, galactaric acid, oxidized starch, starch acetate, glucosamine, galactosamine, mannosamine, ketosamine, acetylglucosamine, acetylmannosamine, acetylneuraminic acid, hydroxypropyl starch, carboxy Examples include methyl starch.
  • (C4b) is preferable from the viewpoint of detergency, and glucosamine, galactosamine, mannosamine, ketosamine, acetylglucosamine, and acetylmannosamine are preferable from the viewpoint of organic residue removal of the cleaning agent for copper wiring semiconductors. From the viewpoint of the stability of the copper wiring semiconductor cleaning agent, glucosamine, galactosamine, mannosamine and ketosamine are more preferable, and glucosamine and mannosamine are particularly preferable.
  • the polyvalent hydroxyl group-containing aromatic hydrocarbon in the polyvalent hydroxyl group-containing compound (C) is excluded from the viewpoint of easily remaining on the insulating film as an organic residue after washing.
  • hydroquinone, gallic acid, and the like are not desirable because they remain on the insulating film as organic residues even though the detergency is not improved.
  • the polyvinyl alcohols (C3) may further contain an ester group in addition to the hydroxyl group, but other (C1), (C2), (C4 ) Excludes compounds having an ester group in addition to the hydroxyl group.
  • a compound containing an ester group is generally not desirable because it is poor in stability of the cleaning agent, such as being hydrolyzed in the cleaning agent to form a compound that is hardly soluble in water.
  • ascorbic acid has an ester group in addition to the four hydroxyl groups, and does not fall under (C) of the present invention.
  • polyvalent hydroxyl group-containing compound (C) one type of compound may be used alone, or a plurality of types of compounds may be used in combination. Of the (C1) to (C4) as the polyvalent hydroxyl group-containing compound (C), (C1) is preferred.
  • the ratio n1 / n2 is the viewpoint of the cleaning properties and solubility of the cleaning agent for copper wiring semiconductors. Therefore, it is usually 0.05 to 1.0, preferably 0.1 to 1.0, more preferably 0.15 to 1.0, and particularly preferably 0.3 to 1.0.
  • n1 / n2 is usually 0.1 to 1.0, preferably 0.15 to 1.0, more preferably 0.5 to 1.0, and particularly preferably 0.8 to 1.0. 1.0.
  • n1 / n2 is usually 0.05 to 0.8, preferably 0.1 to 0.8, and more preferably 0.3 to 0.8. In the case of (C2), it is considered that there is no compound having n1 / n2 greater than 0.8.
  • n1 / n2 is usually 0.05 to 0.5, preferably 0.1 to 0.5, more preferably 0.3 to 0.5. In the case of (C3), it is considered that there is no compound having n1 / n2 greater than 0.5.
  • n1 / n2 is usually 0.1 to 1.0, preferably 0.3 to 1.0, more preferably 0.5 to 1.0, more preferably 0.7 to 1. .0.
  • the content of the polyhydric hydroxyl group-containing compound (C) when used as a cleaning agent is selected from the viewpoints of detergency and copper corrosion inhibition, organic amine (A), quaternary ammonium compound (B), polyhydric hydroxyl group-containing compound (C). ), Hydroxycarboxylic acid (D) and water (W) based on the total weight, usually 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, more preferably 0.01 to 6% by weight. %, More preferably 0.01 to 4% by weight.
  • these contents are organic amine (A), quaternary ammonium compound (B), polyvalent hydroxyl group-containing compound (C), hydroxycarboxylic acid (D) and water ( Based on the total weight of W), it is preferably 0.001 to 5% by weight, more preferably 0.01 to 2% by weight, more preferably 0.05 to 2% by weight.
  • the content is the sum of organic amine (A), quaternary ammonium compound (B), polyvalent hydroxyl group-containing compound (C), hydroxycarboxylic acid (D) and water (W). Based on the weight, it is preferably 0.0001 to 2% by weight, more preferably 0.0005 to 0.5% by weight, more preferably 0.001 to 0.1% by weight.
  • the content is the total weight of organic amine (A), quaternary ammonium compound (B), polyvalent hydroxyl group-containing compound (C), hydroxycarboxylic acid (D) and water (W). Based on this, it is preferably 0.01 to 20% by weight, more preferably 0.05 to 10% by weight, and still more preferably 0.1 to 5% by weight.
  • hydroxycarboxylic acid (D) examples include hydroxytricarboxylic acid (D1), hydroxytetracarboxylic acid (D2), and combinations thereof.
  • Examples of the hydroxytricarboxylic acid (D1) include partially esterified products of citric acid, pentanetetracarboxylic acid and propylene glycol.
  • Examples of the hydroxytetracarboxylic acid (D2) include partially esterified products of benzenepentacarboxylic acid and ethylene glycol.
  • hydroxycarboxylic acid (D) hydroxytricarboxylic acid (D1) is preferable from the viewpoint of copper corrosion inhibition, and citric acid is particularly preferable.
  • the content of the hydroxycarboxylic acid (D) is usually 0.05 to 50 based on the total number of moles of the organic amine (A) and the quaternary ammonium compound (B) from the viewpoint of copper corrosion suppression and metal residue removal.
  • the mol% is preferably 0.1 to 40 mol%, more preferably 1 to 33 mol%, and particularly preferably 5 to 25 mol%.
  • the electrical conductivity ( ⁇ S / cm; 25 ° C.) of water (W) is from the viewpoint of cleanability, availability, and prevention of re-contamination of copper wiring (reattachment of metal ions in water to copper wiring). In general, it is 0.055 to 0.2, preferably 0.056 to 0.1, and more preferably 0.057 to 0.08. As such water with low electrical conductivity, ultrapure water is preferable.
  • the electric conductivity is measured according to JIS K0400-13-10: 1999.
  • the content of water (W) when used as a cleaning agent is organic amine (A), quaternary ammonium compound (B), polyhydric hydroxyl group-containing compound (C), hydroxycarboxylic acid from the viewpoints of detergency and solution viscosity.
  • organic amine (A) quaternary ammonium compound (B)
  • polyhydric hydroxyl group-containing compound (C) hydroxycarboxylic acid from the viewpoints of detergency and solution viscosity.
  • the cleaning agent for copper wiring semiconductor of the present invention is an essential component other than organic amine (A), quaternary ammonium compound (B), polyvalent hydroxyl group-containing compound (C), hydroxycarboxylic acid (D) and water (W). If necessary, a surfactant (F1), a water-soluble reducing agent (F2), a complexing agent (F3) and the like may be added as the other component (F).
  • Surfactant (F1) can be added from the viewpoint of improving organic residue removability and metal impurity removability.
  • examples of such surfactants include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants.
  • the content of the surfactant may be an amount necessary to reduce the surface tension of the cleaning agent, and based on the weight of the cleaning agent for copper wiring semiconductor (E) of the present invention, Usually, it is 0.001 to 1% by weight, preferably 0.005 to 0.3% by weight, particularly preferably 0.01 to 0.1% by weight.
  • Examples of the water-soluble reducing agent (F2) include organic reducing agents and inorganic reducing agents.
  • Examples of organic reducing agents include oxalic acid (salt), hydrogen oxalate (salt), C6-9 aldehydes, C6-30 phenolic compounds and benzaldehyde, and inorganic reducing agents include sulfurous acid (salt) and thiosulfuric acid ( Salt).
  • organic reducing agents are preferred from the viewpoints of water solubility and copper corrosion inhibition effect, more preferably aliphatic organic reducing agents, and particularly preferably oxalic acid (salt).
  • the content of the water-soluble reducing agent is usually 0. 0 based on the weight of the cleaning agent for copper wiring semiconductor (E) of the present invention from the viewpoint of improving the corrosion inhibition effect of the copper wiring. It is 001 to 1.0% by weight, more preferably 0.01 to 0.5% by weight, and particularly preferably 0.05 to 0.1% by weight.
  • Complexing agent (F3) includes C1-6 aromatic or aliphatic hydroxycarboxylic acid (salt), C9-23 heterocyclic group having at least one of hydroxyl group or carboxyl group, C6-9 phosphonic acid (Salt) etc. are mentioned.
  • aliphatic hydroxycarboxylic acid (salt) and polycarboxylic acid (salt) are preferred, and aliphatic hydroxycarboxylic acid (salt) is particularly preferred from the viewpoint of improving the copper corrosion inhibition effect.
  • the content of the complexing agent is usually from 0.001 to 0.001 based on the weight of the cleaning agent (E) for copper wiring semiconductor of the present invention from the viewpoint of improving the corrosion inhibiting effect of the copper wiring. It is 0.5% by weight, preferably 0.01 to 0.3% by weight, particularly preferably 0.05 to 0.1% by weight. When the content of the complexing agent is more than 0.5% by weight, the corrosion inhibiting effect is lowered.
  • the cleaning agent for a copper wiring semiconductor of the present invention comprises an organic amine (A), a quaternary ammonium compound (B), a polyvalent hydroxyl group-containing compound (C), a hydroxycarboxylic acid (D), and other components (F) as necessary. It can be produced by mixing with water (W).
  • the mixing method is not particularly limited, but from the viewpoint of easy and uniform mixing in a short time, water (W), polyhydric hydroxyl group-containing compound (C) and hydroxycarboxylic acid (D) are mixed, followed by A method of mixing the organic amine (A) and, if necessary, the other component (F) is preferable.
  • the temperature and time for uniform mixing are not limited and can be determined appropriately according to the scale and equipment to be manufactured.
  • a stirrer or a disperser can be used.
  • the stirrer include a mechanical stirrer and a magnetic stirrer.
  • the disperser include a homogenizer, an ultrasonic disperser, a ball mill, and a bead mill.
  • the copper wiring semiconductor cleaning agent of the present invention can be used in a cleaning method for cleaning a semiconductor substrate or a semiconductor element having a copper wiring.
  • a cleaning method for cleaning a semiconductor substrate or a semiconductor element having a copper wiring a single wafer method and a batch method can be given.
  • the single wafer method is a method in which a semiconductor substrate or a semiconductor element is rotated one by one, and a cleaning is performed using a brush while injecting a cleaning agent for a copper wiring semiconductor.
  • the batch method is a plurality of semiconductor substrates or semiconductor elements. Is cleaned by immersing it in a cleaning agent for copper wiring semiconductors.
  • the copper wiring semiconductor cleaning agent (E) of the present invention is used in the process of manufacturing a semiconductor substrate or a semiconductor element having copper wiring, after resist development, after dry etching, after wet etching, after dry ashing, after resist stripping, and CMP.
  • CMP Chemical Mechanical Polishing
  • process (I) a cleaning process
  • it is preferably used in the cleaning step after CMP treatment.
  • a step (II) of capping with a silicon compound is included after the above step (I) for the purpose of forming the next copper wiring pattern on the upper layer. Since the cleaning agent for copper wiring semiconductor (E) of the present invention is excellent not only on the copper wiring but also on the organic residue removal property and metal impurity removal property on the insulating film, it can be easily used in the step (II). Silicon compounds can be capped. Examples of the silicon compound to be capped include silicon oxide, silicon nitride, and silicon carbide.
  • Example 1 Put 96.67 parts of water in a polyethylene container, 0.035 parts of monoethanolamine (A-1) (trade name: 2-aminoethanol, purity 97%, Wako Pure Chemical Industries, Ltd.), 25% tetramethylammonium hydroxide Aqueous solution (B-1) (trade name: 25% tetramethylammonium hydroxide solution, 25% purity aqueous solution, manufactured by Tama Chemical Co., Ltd.) 2.88 parts, D-sorbitol (C-1) (trade name: D-sorbitol, Purity 98%, manufactured by Wako Pure Chemical Co., Ltd.
  • A-1 monoethanolamine
  • B-1 trade name: 25% tetramethylammonium hydroxide solution, 25% purity aqueous solution, manufactured by Tama Chemical Co., Ltd.
  • C-1 D-sorbitol, Purity 98%, manufactured by Wako Pure Chemical Co., Ltd.
  • citric acid (trade name: citric acid, purity 99.5%, manufactured by Wako Pure Chemical Industries, Ltd., equivalent to hydroxycarboxylic acid (D)) 0.1 part. Then, the mixture was stirred with a magnetic stirrer to obtain a copper wiring semiconductor cleaning agent (E-1) of the present invention.
  • Examples 2 to 17 The components were blended in the same manner as in Example 1 at the blending ratio shown in Table 1, to obtain copper wiring semiconductor cleaning agents (E-2) to (E-17).
  • the content of each component of the organic amine (A), the quaternary ammonium compound (B), the polyvalent hydroxyl group-containing compound (C), and the hydroxycarboxylic acid (D) is shown by weight%.
  • the 25% tetramethylammonium hydroxide solution (B-1) was blended as the quaternary ammonium compound (B), it was blended in such a manner that the solid content was a predetermined content.
  • TMAH tetramethylammonium hydroxide choline: (hydroxyethyl) trimethylammonium hydroxide
  • TEAH tetraethylammonium hydroxide
  • PVA polyvinyl alcohol PVA having a weight average molecular weight of 250,000 and a saponification degree of 82%
  • Mw 10,000 weight
  • Polyvinyl alcohol S-PVA (Mw 400,000) having an average molecular weight of 10,000 and a saponification degree of 65%: a compound obtained by modifying polyvinyl alcohol having a weight average molecular weight of 400,000 and a saponification degree of 80% with sulfonic acid
  • TMAH tetramethylammonium hydroxide
  • PGME propylene glycol monomethyl ether
  • HEDA 1-hydroxyethane-1,2-dicarboxylic acid
  • Table 2 shows propylene glycol monomethyl ether (PGME) as components other than (A) to (D).
  • HEDA propylene glycol monomethyl ether
  • PGME is a compound having only one hydroxyl group
  • ascorbic acid is a compound having an ester group in addition to four hydroxyl groups
  • gallic acid is an aromatic hydrocarbon compound having three hydroxyl groups, the (C1 ) To (C4).
  • lactic acid is a hydroxy monocarboxylic acid
  • HEDA is a hydroxy dicarboxylic acid
  • trimellitic acid is a tricarboxylic acid not containing a hydroxyl group
  • pyromellitic acid is a tetracarboxylic acid not containing a hydroxyl group, it falls under (D) of the present invention. do not do.
  • Copper wiring semiconductor cleaning agents (E-1) to (E-17) of the present invention prepared in Examples 1 to 17 and copper wiring semiconductor cleaning agents for comparison prepared in Comparative Examples 1 to 12
  • the removal rate of organic residues (benzotriazole and quinaldic acid), benzotriazole removal rate, copper corrosion inhibition performance, and metal residue removability of (E′-1) to (E′-12) were measured by the following methods: evaluated. The evaluation results are shown in Table 3.
  • the organic residue removal rate was measured by a QCM (Quartz Crystal Microbalance) method according to the following procedure.
  • the QCM method is a measurement method that utilizes the principle that when a substance is adsorbed on the surface of a quartz crystal vibrating at a constant frequency, the frequency decreases by the amount of the substance, and when desorbed, the frequency increases.
  • a mass change measuring device HZ-5000 type, manufactured by Hokuto Denko
  • Two types of organic residues were evaluated: benzotriazole and quinaldic acid.
  • Organic residue liquid 1 organic residue of benzotriazole
  • organic residue liquid 2 Organic residue liquid 2 (Organic residue of quinaldic acid) 30 g of hydrogen peroxide solution with a concentration of 30%, 0.8 g of quinaldic acid, 2.0 g of maleic acid, 0.4 g of ammonium dodecylbenzenesulfonate, and 200 g of water are mixed, and the pH is adjusted to 9 with an aqueous potassium hydroxide (KOH) solution.
  • KOH potassium hydroxide
  • the QCM electrode was immersed in a 5% tetramethylammonium hydroxide aqueous solution for 120 seconds and then immersed in 1 L of water for 60 seconds to prepare a QCM electrode to which an organic residue containing quinaldic acid was adhered.
  • the benzotriazole removal rate was evaluated according to the following procedure.
  • (1) Cleaning of a copper-plated silicon wafer A wafer in which a silicon wafer is copper-plated (manufactured by Advanced Material Technology, "Cu-plated 10000A Wafer", copper-plated film thickness 1.0 ⁇ m) is longitudinally 1. It was cut into 5 cm ⁇ 1.5 cm, immersed in a 10% aqueous acetic acid solution for 1 minute, and then washed with water.
  • the amount of benzotriazole attached to the copper-plated wafer was determined by measuring the amount of nitrogen derived from benzotriazole using an X-ray photoelectron spectrometer (ESCA-5400, manufactured by ULVAC-PHI). It confirmed by measuring using. Specifically, using XPS, the number of photoelectrons was measured in a binding energy range of 397 eV to 399 eV, and a peak area value in a range of 397.5 to 398.4 eV derived from nitrogen was obtained. As the soft X-ray, MgK ⁇ ray (1253.6 eV) was used.
  • Xa Peak area value of nitrogen derived from benzotriazole before organic residue removal.
  • Xb Peak area value of nitrogen derived from benzotriazole after organic residue removal.
  • the copper corrosion suppression performance was evaluated by immersing the copper-plated wafer in a cleaning agent for copper wiring semiconductors and then quantifying the concentration of copper eluted from the copper-plated wafer. It was determined that the smaller the copper elution amount per unit area, the better the copper corrosion inhibition performance.
  • the concentration of copper was measured with an ICP-MS analyzer (inductively coupled plasma mass spectrometer) (Agilent Technology, Agilent 7500cs type).
  • a copper-plated wafer was cut into a length of 1.0 cm and a width of 2.0 cm, immersed in a 10% aqueous acetic acid solution for 1 minute, and then washed with water.
  • Cu con Copper concentration in the measurement solution measured by ICP-MS analysis (ppm ( ⁇ g / g))
  • C1 Liquid amount (g) of cleaning agent for copper wiring semiconductor dipped in a copper plated wafer
  • C2 Liquid amount (g) of cleaning agent for copper wiring semiconductor taken out before pH adjustment
  • C3 Amount of measurement liquid (g)
  • S Cu Area of the copper plating surface in the copper plating wafer (cm 2 )
  • TEOS tetraethoxysilane
  • P-TEOS 1.5 ⁇ silicon wafer coated with tetraethoxysilane
  • film thickness of tetraethoxysilane 1.5 ⁇ m.
  • TEOS wafer was cut into a length of 1.0 cm ⁇ width of 2.0 cm, washed with isopropyl alcohol, then immersed in a 1% aqueous citric acid solution for 1 minute, and washed with water.
  • test piece was taken out from the cleaning agent for copper wiring semiconductor after the test piece was immersed in 10 g of the cleaning agent for copper wiring semiconductor for comparison with the present invention for 1 minute.
  • Zn con zinc concentration (ppb (ng / g)) in the measurement liquid quantified by ICP-MS analysis
  • D1 Liquid amount (g) of the cleaning agent for copper wiring semiconductor in which the test piece was immersed
  • D2 Liquid amount (g) of cleaning agent for copper wiring semiconductor taken out before pH adjustment
  • D3 Amount of measurement liquid (g)
  • S TEOS Area of the TEOS coating surface on the TEOS wafer (cm 2 )
  • the cleaning agent for copper wiring semiconductors of the present invention has excellent organic residue (benzotriazole, quinaldic acid, etc.) removability, copper wiring corrosion inhibition ability, and removal of metal residues derived from abrasives and polishing equipment. It can be suitably used as a semiconductor cleaning agent for wiring.
  • the cleaning agent for copper wiring semiconductor of the present invention is excellent not only on the copper wiring but also on the organic residue removal property and metal impurity removal property on the insulating film. Therefore, after wet etching, resist stripping, CMP treatment In the step of capping the silicon compound following the washing step such as before and after, the silicon compound can be easily capped.

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Abstract

L'invention porte sur un agent de nettoyage pour des semi-conducteurs à câblage de cuivre, lequel agent présente des performances de retrait élevées de résidus organiques (benzotriazole et acide quinaldique) formés durant une étape de polissage, tout en ayant un effet de suppression élevé d'une corrosion d'un câblage en cuivre. L'agent de nettoyage présente également d'excellentes performances de retrait de résidus métalliques sur un film isolant. De façon spécifique, l'invention porte sur un agent de nettoyage pour semi-conducteurs à câblage de cuivre, lequel agent contient, comme composants indispensables, un amine organique (A), un composé d'ammonium quaternaire (B), un composé contenant un groupe hydroxyle polyvalent spécifique (C), au moins un acide hydroxycarboxylique (D) choisi dans le groupe comprenant des acides hydroxytricarbolyxiques et des acides hydroxytétracarboxyliques, et de l'eau (W).
PCT/JP2009/000294 2009-01-27 2009-01-27 Agent de nettoyage pour semi-conducteur à câblage de cuivre Ceased WO2010086893A1 (fr)

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JP2013049753A (ja) * 2011-08-30 2013-03-14 Dongwoo Fine-Chem Co Ltd 洗浄剤組成物及びそれを用いた液晶表示装置用アレイ基板の製造方法
WO2013176122A1 (fr) * 2012-05-25 2013-11-28 日産化学工業株式会社 Composition de solution de polissage pour des tranches
WO2014017183A1 (fr) * 2012-07-24 2014-01-30 三井金属鉱業株式会社 Film d'électrode et élément électroluminescent organique
CN105190445A (zh) * 2013-05-09 2015-12-23 Az电子材料（卢森堡）有限公司 刻蚀用清洗液以及使用其的图案形成方法
WO2016151645A1 (fr) * 2015-03-24 2016-09-29 パナソニックＩｐマネジメント株式会社 Liquide de décapage de produit de réserve
JP2018127578A (ja) * 2017-02-10 2018-08-16 荒川化学工業株式会社 防錆膜用の除去剤
CN110873672A (zh) * 2018-08-30 2020-03-10 西部超导材料科技股份有限公司 一种wic镶嵌线铜比测量的方法
JP2020096053A (ja) * 2018-12-11 2020-06-18 三菱ケミカル株式会社 洗浄液、洗浄方法及び半導体ウェハの製造方法
CN115895802A (zh) * 2022-11-10 2023-04-04 江西兆驰半导体有限公司 一种去胶液、制备方法及应用

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Cited By (20)

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Publication number Priority date Publication date Assignee Title
JP2013049753A (ja) * 2011-08-30 2013-03-14 Dongwoo Fine-Chem Co Ltd 洗浄剤組成物及びそれを用いた液晶表示装置用アレイ基板の製造方法
WO2013176122A1 (fr) * 2012-05-25 2013-11-28 日産化学工業株式会社 Composition de solution de polissage pour des tranches
US9133366B2 (en) 2012-05-25 2015-09-15 Nissan Chemical Industries, Ltd. Polishing liquid composition for wafers
JPWO2013176122A1 (ja) * 2012-05-25 2016-01-14 日産化学工業株式会社 ウェーハ用研磨液組成物
WO2014017183A1 (fr) * 2012-07-24 2014-01-30 三井金属鉱業株式会社 Film d'électrode et élément électroluminescent organique
CN104472012A (zh) * 2012-07-24 2015-03-25 三井金属矿业株式会社 电极箔和有机发光器件
US20150207096A1 (en) * 2012-07-24 2015-07-23 Mitsui Mining & Smelting Co., Ltd. Electrode Foil and Organic Light-Emitting Device
CN104472012B (zh) * 2012-07-24 2016-06-29 三井金属矿业株式会社 电极箔和有机发光器件
JPWO2014017183A1 (ja) * 2012-07-24 2016-07-07 三井金属鉱業株式会社 電極箔及び有機発光デバイス
US9508951B2 (en) 2012-07-24 2016-11-29 Mitsui Mining & Smelting Co., Ltd. Electrode foil and organic light-emitting device
CN105190445B (zh) * 2013-05-09 2019-07-05 Az电子材料（卢森堡）有限公司 刻蚀用清洗液以及使用其的图案形成方法
CN105190445A (zh) * 2013-05-09 2015-12-23 Az电子材料（卢森堡）有限公司 刻蚀用清洗液以及使用其的图案形成方法
WO2016151645A1 (fr) * 2015-03-24 2016-09-29 パナソニックＩｐマネジメント株式会社 Liquide de décapage de produit de réserve
KR20180092887A (ko) * 2017-02-10 2018-08-20 아라까와 가가꾸 고교 가부시끼가이샤 방청막용 제거제
JP2018127578A (ja) * 2017-02-10 2018-08-16 荒川化学工業株式会社 防錆膜用の除去剤
KR102335365B1 (ko) * 2017-02-10 2021-12-03 아라까와 가가꾸 고교 가부시끼가이샤 방청막용 제거제
CN110873672A (zh) * 2018-08-30 2020-03-10 西部超导材料科技股份有限公司 一种wic镶嵌线铜比测量的方法
JP2020096053A (ja) * 2018-12-11 2020-06-18 三菱ケミカル株式会社 洗浄液、洗浄方法及び半導体ウェハの製造方法
JP7192461B2 (ja) 2018-12-11 2022-12-20 三菱ケミカル株式会社 洗浄液、洗浄方法及び半導体ウェハの製造方法
CN115895802A (zh) * 2022-11-10 2023-04-04 江西兆驰半导体有限公司 一种去胶液、制备方法及应用

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