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WO2022244593A1 - Composition de décomposition/nettoyage, son procédé de production, et procédé de nettoyage de polymère adhésif - Google Patents

Composition de décomposition/nettoyage, son procédé de production, et procédé de nettoyage de polymère adhésif Download PDF

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Publication number
WO2022244593A1
WO2022244593A1 PCT/JP2022/018477 JP2022018477W WO2022244593A1 WO 2022244593 A1 WO2022244593 A1 WO 2022244593A1 JP 2022018477 W JP2022018477 W JP 2022018477W WO 2022244593 A1 WO2022244593 A1 WO 2022244593A1
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Prior art keywords
cleaning composition
compound
mass
substituted
composition according
Prior art date
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PCT/JP2022/018477
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English (en)
Japanese (ja)
Inventor
晋 中崎
邦明 宮原
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昭和電工株式会社
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Priority to KR1020237026897A priority Critical patent/KR20230129500A/ko
Priority to JP2023522582A priority patent/JPWO2022244593A1/ja
Publication of WO2022244593A1 publication Critical patent/WO2022244593A1/fr

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    • 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
    • C11D7/50—Solvents
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
    • C11D7/5095—Mixtures including solvents containing other heteroatoms than oxygen, e.g. nitriles, amides, nitroalkanes, siloxanes or thioethers
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B08—CLEANING
    • B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
    • B08B3/00—Cleaning by methods involving the use or presence of liquid or steam
    • B08B3/04—Cleaning involving contact with liquid
    • 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
    • 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
    • C11D7/28—Organic compounds containing halogen
    • 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
    • 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
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5013—Organic solvents 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
    • C11D7/5077—Mixtures of only oxygen-containing solvents
    • C11D7/5086—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being different from alcohols, e.g. mixtures of water and ethers
    • 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
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
    • H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting

Definitions

  • the present disclosure relates to a degradable cleaning composition, a method for producing the same, and a method for cleaning an adhesive polymer.
  • the present disclosure is used for decomposing and cleaning an adhesive containing an adhesive polymer used for temporary bonding between a device wafer and a support wafer (carrier wafer), which remains on the device wafer in a semiconductor wafer thinning process. and a method for producing the same, and a method for cleaning an adhesive polymer using the composition.
  • the thickness of each semiconductor wafer is reduced, and multiple semiconductor wafers connected by through-silicon vias (TSV) are stacked.
  • TSV through-silicon vias
  • the surface (rear surface) of the device wafer on which semiconductor devices are formed is thinned by polishing, and then electrodes including TSVs are formed on the rear surface.
  • a support wafer also called a carrier wafer
  • a support wafer is temporarily adhered to the semiconductor device forming surface of the device wafer with an adhesive in order to give the device wafer mechanical strength.
  • Glass wafers or silicon wafers are used as support wafers.
  • a metal wiring or electrode pad containing Al, Cu, Ni, Au, etc., an inorganic film such as an oxide film, a nitride film, or a resin containing polyimide or the like is applied to the polished surface (back surface) of the device wafer as necessary A layer is formed.
  • the device wafer is fixed to the tape by laminating the back surface of the device wafer to the tape having the acrylic adhesive layer fixed by the ring frame.
  • the device wafer is then separated from the support wafer (debonding), the adhesive on the device wafer is stripped off, and the adhesive residue on the device wafer is washed off using a cleaning agent.
  • an adhesive containing a polyorganosiloxane compound with good heat resistance as an adhesive polymer is used.
  • the cleaning agent is required to have two functions of severing Si—O bonds and dissolving decomposition products with a solvent.
  • cleaning agents include those obtained by dissolving a fluorine-based compound such as tetrabutylammonium fluoride (TBAF) in a polar aprotic solvent. Since the fluoride ions in TBAF are involved in the breaking of Si--O bonds through the formation of Si--F bonds, they can impart etching performance to the cleaning agent.
  • Polar aprotic solvents can dissolve TBAF and do not solvate fluoride ions via hydrogen bonding, thus increasing the reactivity of fluoride ions.
  • Non-Patent Document 1 Advanced Materials, 11, 6, 492 (1999)
  • a 1.0 M TBAF solution using aprotic THF as a solvent is used to decompose and dissolve polydimethylsiloxane (PDMS).
  • PDMS polydimethylsiloxane
  • Non-Patent Document 2 (Advanced Materials, 13, 8, 570 (2001)), NMP, DMF and DMSO, which are aprotic solvents like THF, are used as solvents for TBAF.
  • Non-Patent Document 3 (Macromolecular Chemistry and Physics, 217, 284-291 (2016)) describes the results of examining the etching rate of PDMS with TBAF / organic solvent for each solvent, and THF and For DMF, a comparison of etch rates of TBAF solutions using mixed solvents with varying ratios of THF/DMF is also described.
  • the role of the solvent in the decomposition cleaning composition containing a fluorine compound such as TBAF and a solvent is to sufficiently dissolve the highly polar fluorine compound, which is a reactive substance, while ensuring the reactivity of the fluoride ion contained in the fluorine compound. , to dissolve the decomposition products of the adhesive.
  • Aprotic N-substituted amide compounds such as N-methylpyrrolidone (NMP) are capable of dissolving the adhesive decomposition products without adversely affecting fluoride ion reactivity and are therefore useful in dissolving cleaning compositions. It is known that it can be advantageously used as a solvent for
  • aprotic N-substituted amide compound is used as a solvent for the decomposing cleaning composition, a sufficient etching rate (ER) may not be obtained.
  • An object of the present disclosure is to provide a decomposing cleaning composition that exhibits a high etching rate.
  • a decomposition cleaning composition comprising a quaternary alkylammonium fluoride or hydrate thereof and an N-substituted amide compound having two alkyl groups attached to the amide nitrogen atom includes the N-substituted amide compound is inevitably included in oxide derivatives (peroxides, hydroxides, or imide compounds) generated by oxidation, and by setting the content of such oxide derivatives to a predetermined value or less, high etching We have found that speed can be obtained.
  • oxide derivatives peroxides, hydroxides, or imide compounds
  • a decomposition cleaning composition containing (A) an N-substituted amide compound having two alkyl groups bonded to an amide nitrogen atom and (B) a quaternary alkylammonium fluoride or a hydrate thereof as an aprotic solvent.
  • the content of the (A) N-substituted amidated derivative, which is a compound in which two hydrogen atoms on the carbon atom at the ⁇ -position of the amide nitrogen atom of the N-substituted amide compound are substituted with an oxo group is A decomposing cleaning composition having a content of 550 ppm by mass or less.
  • the decomposing cleaning composition according to [1] which has a bromide ion concentration of 100 ppm by mass or less.
  • the (A) N-substituted amide compound has the formula (1): (In Formula (1), R 1 represents an alkyl group having 1 to 4 carbon atoms.)
  • a 2-pyrrolidone derivative compound represented by The N-substituted amidated derivative has the formula (4): (In formula (4), R 1 represents an alkyl group having 1 to 4 carbon atoms.)
  • the (C) ether compound has the formula (2): R2O ( CnH2nO ) xR3 ( 2 ) (In formula (2), R 2 and R 3 are each independently a group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and t-butyl groups.
  • the (C) ether compound has the formula (3): R4OR5 ( 3 ) (In the formula, R 4 and R 5 each independently represent an alkyl group having 4 to 8 carbon atoms.)
  • the quaternary alkylammonium fluoride is a tetraalkylammonium fluoride represented by R 6 R 7 R 8 R 9 N + F- , wherein R 6 to R 9 are each independently a methyl group;
  • Decomposition cleaning comprising mixing the (A) N-substituted amide compound and the (B) quaternary alkylammonium fluoride or its hydrate so that the composition is 550 mass ppm or less.
  • a method of making the composition comprising mixing the (A) N-substituted amide compound and the (B) quaternary alkylammonium fluoride or its hydrate so that the composition is 550 mass ppm or less.
  • the disassembly cleaning composition of the present disclosure exhibits a high etching rate.
  • Example 16 decomposition cleaning compositions of Example 16 (denoted as N 2 ) and Comparative Example 7 (denoted as Air), and tetrabutylammonium bifluoride (denoted as TBAHF2).
  • the decomposition cleaning composition of one embodiment comprises, as an aprotic solvent, (A) an N-substituted amide compound having two alkyl groups attached to the amide nitrogen atom, and (B) a quaternary alkylammonium fluoride or a hydrated form thereof. contains things.
  • an N-substituted amide which is a compound in which two hydrogen atoms on the ⁇ -position carbon atom of the amide nitrogen atom of the N-substituted amide compound are substituted with oxo groups;
  • the content of the oxidized derivative (also simply referred to as “N-substituted amidated oxidized derivative” in the present disclosure) is 550 mass ppm or less.
  • the decomposition cleaning composition of the present disclosure contains an N-substituted amide compound having two alkyl groups bonded to the amide nitrogen atom (also simply referred to as "N-substituted amide compound" in the present disclosure) as an aprotic solvent.
  • N-substituted amide compounds are known to be slowly oxidized on contact with oxygen to produce oxidized derivatives.
  • NMP N-methylpyrrolidone
  • NMS imide compound N-methylsuccinimide
  • the content of the compound in which two hydrogen atoms on the ⁇ -position carbon atom of the amide nitrogen atom of the N-substituted amide compound are substituted with oxo groups is less than or equal to a predetermined value. Therefore, a high etching rate can be obtained.
  • the two alkyl groups in the N-substituted amide compounds may be the same or different.
  • the number of carbon atoms in each alkyl group is preferably 1-10, more preferably 1-5.
  • One alkyl group may participate in the formation of a cyclic amide compound.
  • N-substituted amide compounds also include urea compounds (carbamide compounds) having two alkyl groups attached to the amide nitrogen atom.
  • urea compounds caramide compounds
  • Various compounds can be used as the N-substituted amide compound without particular limitation.
  • Acyclic N-substituted amides such as N,N-dimethylpropionamide, N,N-diethylpropionamide, tetramethylurea, 2-pyrrolidone derivatives, 2-piperidone derivatives, ⁇ -caprolactam derivatives, 1,3-dimethyl- 2-imidazolidinone, 1-methyl-3-ethyl-2-imidazolidinone, 1,3-diethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2 ( Cyclic N-substituted amides such as 1H)-pyrimidinone (N,N'-dimethylpropylene urea). Among these, it is preferable to use cyclic N-substituted amides.
  • the N-substituted amide compounds may be one or a combination of two or more.
  • the N-substituted amide compound has the formula (1): (In Formula (1), R 1 represents an alkyl group having 1 to 4 carbon atoms.) It is a 2-pyrrolidone derivative compound represented by Examples of alkyl groups having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group and t-butyl group.
  • Examples of 2-pyrrolidone derivative compounds represented by formula (1) include N-methylpyrrolidone (NMP), N-ethylpyrrolidone (NEP), N-propylpyrrolidone, N-butylpyrrolidone and the like.
  • N-substituted amide compounds of formula (1) where R 1 is a methyl group or an ethyl group are A certain 2-pyrrolidone derivative compound is preferable, and a 2-pyrrolidone derivative compound in which R 1 is a methyl group in formula (1), that is, N-methylpyrrolidone is more preferable.
  • the content of the N-substituted amide compound in the decomposition cleaning composition is 70 to 99.99% by mass, preferably 80 to 99.95% by mass, more preferably 90 to 99.9% by mass. % is more preferable.
  • the decomposition cleaning composition contains an ether compound, which will be described later, the total content of the N-substituted amide compound and the ether compound in the decomposition cleaning composition is preferably 70 to 99.99% by mass, more preferably 80 to 99.95%. % by mass is more preferred, and 90 to 99.9% by mass is even more preferred.
  • the content of the N-substituted amidated derivative in the decomposition cleaning composition of one embodiment is 550 mass ppm or less.
  • the content of N-substituted amidated derivatives is determined by gas chromatography using the conditions described in the Examples.
  • the content of the N-substituted amidated derivative in the decomposing cleaning composition is preferably 500 mass ppm or less, more preferably 450 mass ppm or less.
  • the N-substituted amidated derivative is represented by Formula (4): (In formula (4), R 1 represents an alkyl group having 1 to 4 carbon atoms.) is an N-substituted succinimide compound represented by
  • Quaternary alkylammonium fluoride or its hydrate release fluoride ions that participate in breaking Si—O bonds.
  • the quaternary alkylammonium moiety allows the salts, quaternary alkylammonium fluorides, to dissolve in aprotic solvents.
  • Various compounds can be used as the quaternary alkylammonium fluoride without particular limitation. Hydrates of quaternary alkylammonium fluorides include, for example, trihydrate, tetrahydrate and pentahydrate.
  • the quaternary alkylammonium fluoride may be one or a combination of two or more.
  • the quaternary alkylammonium fluoride nonhydrate and hydrate can be used in any ratio.
  • the quaternary alkylammonium fluoride is a tetraalkylammonium fluoride represented by R 6 R 7 R 8 R 9 N + F- , where R 6 to R 9 are each independently a methyl group , an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group. From the standpoint of availability, all of R 6 to R 9 are preferably the same alkyl group.
  • Such quaternary alkylammonium fluorides include tetramethylammonium fluoride, tetraethylammonium fluoride, tetrapropylammonium fluoride, tetrabutylammonium fluoride and the like. From the viewpoints of decomposition and cleaning performance, availability, price, etc., the quaternary alkylammonium fluoride is preferably tetrabutylammonium fluoride (TBAF).
  • TBAF tetrabutylammonium fluoride
  • the content of the quaternary alkylammonium fluoride in the decomposing cleaning composition is 0.01 to 10% by mass.
  • “content of quaternary alkylammonium fluoride” means, when the composition contains a hydrate of quaternary alkylammonium fluoride, quaternary It is a value converted as the mass of only the alkylammonium fluoride.
  • the content of the quaternary alkylammonium fluoride in the decomposing and cleaning composition is preferably 0.01 to 5% by mass, more preferably 0.05 to 2% by mass, and more preferably 0.1 to 1% by mass. % by mass is more preferred.
  • the content of the quaternary alkylammonium fluoride in the decomposition cleaning composition is preferably 0.5 to 9% by mass, more preferably 1 to 8% by mass. It is more preferably ⁇ 5% by mass or 4 to 8% by mass.
  • the content of quaternary alkylammonium fluorides in the decomposition cleaning composition may be reduced to 4. % by mass or less, or 3% by mass or less. If a higher etching rate is required, the content of the quaternary alkylammonium fluoride in the decomposition cleaning composition may be 5 wt% or more, 6 wt% or more, or 7 wt% or more.
  • the decomposition cleaning composition may further contain an ether compound as an aprotic solvent.
  • Ether compounds can be combined with N-substituted amide compounds to form mixed solvent systems that exhibit a high affinity for adhesive surfaces.
  • a composition using such a mixed solvent system can achieve a high etching rate by effectively utilizing the reaction activity of the quaternary alkylammonium fluoride.
  • Various compounds can be used as the ether compound without any particular limitation.
  • Ether compounds may be one or a combination of two or more.
  • the ether compound preferably does not contain an ester structure or an amide structure.
  • the ether compound has the formula (2): R2O ( CnH2nO ) xR3 ( 2 )
  • R 2 and R 3 are each independently a group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and t-butyl groups. represents an alkyl group selected from the above, n is 2 or 3, and x is an integer of 1 to 4.
  • dialkyl ethers of glycols represented by formula (2) ethylene glycol dimethyl ether, propylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, tripropylene glycol dimethyl ether, tripropylene glycol diethyl ether, tripropylene glycol di-n-butyl ether, tetra ethylene glycol dimethyl ether, tetrapropylene glycol dimethyl ether and the like.
  • the dialkyl ether of glycol represented by formula (2) is preferably diethylene glycol dimethyl ether or dipropylene glycol dimethyl ether from the viewpoints of decomposition cleaning performance, availability, price, etc., and a high etching rate can be obtained with a wide range of compositions. Therefore, dipropylene glycol dimethyl ether is more preferable.
  • the content of the dialkyl ether of the glycol represented by formula (2) is preferably 10 to 80% by mass, preferably 15 to 70% by mass, when the aprotic solvent is 100% by mass. More preferably, it is 20 to 60% by mass. In another embodiment, the content of the dialkyl ether of the glycol represented by formula (2) is preferably 0 to 60% by mass, preferably 3 to 50% by mass, when the aprotic solvent is 100% by mass. % by mass is more preferred, and 5 to 40% by mass is even more preferred.
  • the ether compound has the formula (3): R4OR5 ( 3 ) (In the formula, R 4 and R 5 each independently represent an alkyl group having 4 to 8 carbon atoms.) Including a dialkyl ether represented by
  • the ether compound may include a dialkyl ether of glycol represented by formula (2) and a dialkyl ether represented by formula (3).
  • Dialkyl ethers represented by formula (3) include dibutyl ether, dipentyl ether, dihexyl ether, diheptyl ether, dioctyl ether, butylhexyl ether, butyloctyl ether, and the like.
  • the dialkyl ether represented by formula (3) is preferably dibutyl ether from the viewpoints of decomposition and washing performance, availability, price, and the like.
  • the content of the dialkyl ether represented by formula (3) is preferably 0 to 50% by mass, more preferably 1 to 35% by mass, when the aprotic solvent is 100% by mass. , more preferably 2 to 30% by mass.
  • a higher etching rate can be obtained by setting the content of the dialkyl ether represented by the formula (3) to 0% by mass or more and 50% by mass or less.
  • the content of the dialkyl ether represented by formula (3) is preferably 30 to 70% by mass, preferably 35 to 65% by mass, when the aprotic solvent is 100% by mass. It is more preferable to set it to 40 to 60% by mass.
  • the ether compound has a flash point of 21°C or higher.
  • Tetrahydrofuran THF, flash point -17°C, hazardous material Class 4 class 1 petroleum
  • the requirements for equipment, work environment, etc. in the production and use of the composition can be reduced.
  • diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, and dibutyl ether have flash points of 51° C., 60° C., and 25° C., respectively.
  • the flash point is measured by the tag sealing method (JIS K 2265-1:2007).
  • the content of the N-substituted amide compound is 10-90% by weight and the content of the ether compound is 90-10% by weight, based on 100% by weight of the aprotic solvent.
  • the content of the N-substituted amide compound is preferably 15 to 85% by mass, and the content of the ether compound is preferably 85 to 15% by mass. is more preferably 25 to 65% by mass, and the content of the ether compound is 75 to 35% by mass.
  • the content of the N-substituted amide compound is 40 to 80% by mass and the content of the ether compound is 60 to 20% by mass when the aprotic solvent is 100% by mass. .
  • the quaternary alkylammonium fluoride and its hydrate can be uniformly dissolved in the composition, and various adhesive surfaces can be coated. A high etching rate can be obtained.
  • the content of the N-substituted amide compound is 20 to 90% by mass
  • the content of the dialkyl ether of the glycol represented by formula (2) is 10 to 80% by mass
  • the content of the dialkyl ether represented by formula (3) is 0 to 30% by mass.
  • the content of the N-substituted amide compound is 25 to 80% by mass
  • the content of the dialkyl ether of the glycol represented by formula (2) is 20 to 60% by mass
  • the content is represented by formula (3)
  • the content of dialkyl ether is 0 to 30% by mass.
  • the content of the N-substituted amide compound is 20 to 90% by mass, and the content of the dialkyl ether of the glycol represented by formula (2) is 0 to 70% by mass, and the content of the dialkyl ether represented by formula (3) is 0 to 30% by mass.
  • the content of the N-substituted amide compound is 30 to 85% by mass
  • the content of the dialkyl ether of the glycol represented by formula (2) is 3 to 50% by mass
  • the content is represented by formula (3)
  • the content of dialkyl ether is 0 to 30% by mass.
  • the content of the N-substituted amide compound is 20 to 80% by mass and the dialkyl ether of the glycol represented by formula (2) is contained when the aprotic solvent is 100% by mass.
  • the content of the dialkyl ether represented by formula (3) is 30 to 60% by mass.
  • the decomposing cleaning composition may contain additives such as antioxidants, surfactants, antiseptics, antifoaming agents, etc. as optional components within a range that does not significantly impair the effects of the present invention.
  • the dissolution cleaning composition is substantially free or free of protic solvents.
  • the content of protic solvent in the composition can be 5% by mass or less, 3% by mass or less, or 1% by mass or less.
  • a protic solvent that may be included in the composition may be water derived from a quaternary alkylammonium fluoride hydrate.
  • the disintegrating cleaning composition is substantially free or free of aprotic solvents selected from ketones and esters.
  • the content of aprotic solvents selected from ketones and esters in the composition can be 1% by mass or less, 0.5% by mass or less, or 0.1% by mass or less.
  • the bromide ion concentration in the decomposition cleaning composition is 100 ppm by weight or less. Bromide ion concentration is determined by ion chromatography using the conditions described in the Examples.
  • the bromide ion concentration in the decomposing cleaning composition is preferably 90 mass ppm or less, more preferably 70 mass ppm or less. Dissolving cleaning compositions may have color variations even when prepared with the same formula. By setting the bromide ion concentration in the decomposing cleaning composition to 100 ppm by mass or less, it is possible to reduce variations in the color of the decomposing cleaning composition.
  • the method for producing the decomposing cleaning composition is not particularly limited.
  • the decomposition cleaning composition can be prepared by mixing the N-substituted amide compound, the quaternary alkylammonium fluoride or its hydrate, and other optional ingredients.
  • the decomposing cleaning composition is preferably prepared by mixing the N-substituted amide compound, the quaternary alkylammonium fluoride or its hydrate, and other optional ingredients under an inert gas atmosphere.
  • an N-substituted amide compound, a quaternary alkylammonium fluoride or a hydrate thereof, and other optional components are stirred and mixed using a stirrer or the like, A method of dissolving a quaternary alkylammonium fluoride or a hydrate thereof in a solvent can be mentioned.
  • the inert gas is preferably argon gas or nitrogen gas, more preferably nitrogen gas.
  • the peroxide value (POV) of the N-substituted amide compound used for producing the decomposing cleaning composition is preferably 10 meq/L or less. Peroxide value is determined by the iodometric titration method using the conditions described in the Examples.
  • the peroxide value of the N-substituted amide compound is more preferably 7 meq/L or less, more preferably 5 meq/L or less.
  • the peroxide value of the N-substituted amide compound serves as an indicator of the degree of oxidation of the N-substituted amide compound.
  • the content of the N-substituted amide oxidation derivative in the decomposition cleaning composition can be reduced, and the decomposition cleaning composition has a high etching rate. can be obtained.
  • the dissolving cleaning composition of the present disclosure can be used as a dissolving cleaning composition for adhesive polymers contained in various adhesives.
  • the adhesive polymer is not particularly limited as long as it can be cleaned using the disassembly cleaning composition of the present disclosure.
  • the adhesive may optionally contain curing agents, curing accelerators, cross-linking agents, surfactants, leveling agents, fillers, and the like.
  • the adhesive polymer contains Si—O bonds.
  • the adhesive polymer becomes low-molecular-weight or loses its crosslinked structure by cleaving the Si—O bond by the fluoride ion of the quaternary alkylammonium fluoride, and becomes soluble in the solvent. Polymer can be removed.
  • the adhesive polymer containing Si—O bonds is preferably a polyorganosiloxane compound. Since the polyorganosiloxane compound contains many siloxane bonds (Si--O--Si), it can be effectively decomposed and cleaned using the decomposing cleaning composition.
  • Examples of polyorganosiloxane compounds include silicone resins such as silicone elastomers, silicone gels, and MQ resins, and modified products thereof such as epoxy modified products, acrylic modified products, methacrylic modified products, amino modified products, and mercapto modified products. .
  • the polyorganosiloxane compound may be a silicone-modified polymer such as silicone-modified polyurethane or silicone-modified acrylic resin.
  • the adhesive polymer is an addition-curable silicone elastomer, silicone gel, or silicone resin.
  • These addition-curable silicones contain ethylenically unsaturated group-containing polyorganosiloxanes, such as vinyl-terminated polydimethylsiloxanes or vinyl-terminated MQ resins, and polyorganohydrogensiloxanes, such as polymethylhydrogensiloxanes, as crosslinkers, It is cured using a hydrosilylation catalyst such as a platinum catalyst.
  • the adhesive polymer may contain at least one selected from the group consisting of methyl group-containing polyorganosiloxane, epoxy group-containing polyorganosiloxane, and phenyl group-containing polyorganosiloxane.
  • These polyorganosiloxanes are preferably at least one selected from the group consisting of polydimethylsiloxane, epoxy group-containing polydimethylsiloxane, and phenyl group-containing polydimethylsiloxane.
  • the addition-curable silicone may be combined with at least one selected from the group consisting of methyl group-containing polyorganosiloxane, epoxy group-containing polyorganosiloxane, and phenyl group-containing polyorganosiloxane.
  • Method for cleaning adhesive polymer Cleaning of the adhesive polymer on a substrate such as a silicon wafer can be done in a variety of ways known in the art using the dissolution cleaning composition.
  • a decomposing cleaning composition is discharged onto the substrate so as to come into contact with the adhesive polymer (spin etch). Examples include spraying the degradable cleaning composition onto the adhesive polymer on the substrate (spray), and immersing the substrate having the adhesive polymer in a tank containing the degradable cleaning composition (dipping).
  • the temperature for disassembly and washing may vary depending on the type and amount of adhesive polymer deposited on the substrate, and is generally 20°C to 90°C, preferably 40°C to 60°C.
  • the time for disassembly and cleaning may vary depending on the type and amount of adhesive polymer deposited on the substrate, and is generally 5 seconds to 10 hours, preferably 10 seconds to 2 hours. Ultrasound may be applied to the bath of the destructive cleaning composition or the substrate during destructive cleaning.
  • the substrate may be rinsed with an alcohol such as isopropyl alcohol (IPA), ion-exchanged water (DIW), or the like, and the substrate may be rinsed with nitrogen gas, air, or the like, under normal pressure or under reduced pressure. It may be dried by heating or the like.
  • IPA isopropyl alcohol
  • DIW ion-exchanged water
  • a method of manufacturing a device wafer includes cleaning an adhesive polymer on the device wafer with a dissolution cleaning composition. After cleaning, the device wafer may be rinsed or dried if desired.
  • the device wafer manufacturing method further includes the following steps: obtaining a device wafer by forming semiconductor devices on a base material such as a silicon wafer; Temporarily bonding the device wafer and the support wafer via an adhesive containing an adhesive polymer, thinning the device wafer by polishing the opposite side (back surface) of the device forming surface of the device wafer, and supporting from the device wafer separating the wafers. Formation of the semiconductor device, temporary bonding of the device wafer and the support wafer, polishing of the back surface of the device wafer, and separation of the device wafer from the support wafer can be performed by conventionally known methods, and are not particularly limited.
  • the disassembly cleaning composition can be used to reclaim support wafers used in the manufacture of device wafers.
  • a method of reclaiming a support wafer includes cleaning the adhesive polymer on the support wafer with a degradative cleaning composition. After cleaning, the support wafer may be rinsed or dried if desired.
  • NMP N-methylpyrrolidone
  • the mixed solution was taken out from the dark place, and 30 mL of distilled water and 8 mL of 1% starch aqueous solution were added to the mixed solution to obtain a sample for titration.
  • a 0.01 M sodium thiosulfate aqueous solution (Kanto Kagaku Co., Ltd.) was added dropwise to the sample for titration using a 2 mL microburette until the color of the mixed solution became colorless and transparent.
  • the peroxide value (POV) was calculated from the following formula, with the volume of the dropped 0.01 M sodium thiosulfate aqueous solution as V (mL).
  • Table 1 shows the peroxide values and NMS concentrations of NMP-1 to NMP-4.
  • TBAF tetrabutylammonium fluoride trihydrate
  • the bromine contained in the sample was absorbed by bubbling the gas generated by combustion decomposition into 5 mL of absorption liquid.
  • An absorption liquid was prepared by the following procedure. 10.6 g of sodium carbonate (special grade, Kanto Kagaku Co., Ltd.) was dissolved in deionized water. A 1 M Na 2 CO 3 aqueous solution was prepared by putting the obtained solution into a 100 mL volumetric flask and making up the volume.
  • bromide ions contained in TBAF.3H 2 O were calculated.
  • the bromide ion concentrations of the two commercial TBAF.3H 2 O were 10 mass ppm and 1000 mass ppm, respectively.
  • TBAF - Br10 TBAF.3H.sub.2O with a bromide ion concentration of 10 mass ppm
  • TBAF - Br1000 TBAF.3H.sub.2O with a bromide ion concentration of 1000 mass ppm
  • Degradative cleaning compositions were prepared using NMP-1 through NMP-4, and TBAF-Br10 and TBAF-Br1000.
  • Example 1 In a glove box filled with nitrogen gas, 4.748 g of TBAF-Br1000 was added to a 125 mL polyethylene container, 35.157 g of NMP-1, 3.504 g of dipropylene glycol dimethyl ether (DPGDME), and 6.598 g. dibutyl ether (DBE) in this order and mixed to dissolve TBAF-Br1000. In this way, a 7.7% by mass TBAF mixed solvent containing 95 mass ppm (calculated value) of bromide ions and having a mass ratio of NMP:DPGDME:DBE of 0.777:0.077:0.146 was decomposed and washed. A composition was prepared. The decomposition cleaning composition was transferred to a 50 mL glass colorimetric tube, sealed with nitrogen gas, and then the colorimetric tube was sealed with a glass stopper.
  • DPGDME dipropylene glycol dimethyl ether
  • DBE dibutyl ether
  • Example 2 In a glove box sealed with nitrogen gas, 3.561 g of TBAF-Br1000 and 1.189 g of TBAF-Br10 were added to a 125 mL polyethylene container, 35.147 g of NMP-1, 3.502 g of DPGDME, 6 TBAF-Br1000 and TBAF-Br10 were dissolved by sequentially charging 0.598 g of DBE and mixing. In this way, a 7.7% by mass TBAF mixed solvent containing 71 mass ppm (calculated value) of bromide ions and having a mass ratio of NMP:DPGDME:DBE of 0.777:0.077:0.146 was decomposed and washed. A composition was prepared. The decomposition cleaning composition was transferred to a 50 mL glass colorimetric tube, sealed with nitrogen gas, and then the colorimetric tube was sealed with a glass stopper.
  • Examples 3 to 15, Comparative Examples 1 to 6 A disassembly cleaning composition was prepared in the same manner as in Example 1 or 2, except that the composition was as shown in Table 2.
  • etch rate (ER) of the dissolving cleaning composition was calculated by dividing the difference in thickness of the specimen before and after immersion by the time immersed in the dissolving cleaning composition.
  • Etching rate (ER) ( ⁇ m / min) [(thickness of test piece before immersion - thickness of test piece after immersion, washing and drying) ( ⁇ m)] / immersion time (3 minutes)
  • Table 2 shows the compositions and evaluation results of Examples 1 to 15 and Comparative Examples 1 to 6.
  • Example 16 and Comparative Example 7 By the same procedure as in Example 1, a decomposition cleaning composition was prepared with a 5% by mass TBAF mixed solvent in which the mass ratio of NMP:DPGDME was 0.764:0.236. The prepared decomposition cleaning composition was stored in a nitrogen gas atmosphere for 16 months to obtain a decomposition cleaning composition of Example 16 having an N-methylsuccinimide (NMS) concentration of 550 ppm or less. A similarly prepared decomposition cleaning composition was stored in an air atmosphere for 16 months to obtain a decomposition cleaning composition of Comparative Example 7 having an N-methylsuccinimide (NMS) concentration of greater than 550 ppm.
  • NPS N-methylsuccinimide
  • FIG. 1 shows the decomposition cleaning compositions of Example 16 (denoted as N2 ) and Comparative Example 7 (denoted as Air), and 19 F of tetrabutylammonium bifluoride (denoted as TBAHF2, manufactured by Sigma-Aldrich Japan G.K.). NMR spectra are shown.
  • the high intensity peak near ⁇ 115 ppm observed in the decomposing cleaning composition of Example 16 is attributed to fluoride ions (F ⁇ ) derived from tetrabutylammonium fluoride.
  • the peak around ⁇ 115 ppm disappeared, and instead the area of the peak around ⁇ 148 to ⁇ 150 ppm attributed to bifluoride ion (HF 2 ⁇ ) increased. .
  • the decomposing cleaning composition of the present invention is suitable for decomposing and cleaning the residue of adhesives used in the thinning process of semiconductor wafers, particularly adhesives containing polyorganosiloxane compounds as adhesive polymers, from device wafers. can be used.

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Abstract

L'invention concerne une composition de décomposition/nettoyage ayant une vitesse de gravure élevée. La composition de décomposition/nettoyage contient : (A) un composé amide N-substitué, dans lequel 2 groupes alkyle sont liés à un atome d'azote amide, en tant que solvant aprotique ; et (B) un fluorure d'alkyle d'ammonium quaternaire ou un hydrate de celui-ci. La teneur en dérivé d'acide amidique N-substitué, qui est un composé dans lequel 2 atomes d'hydrogène sur un atome de carbone en position α de l'atome d'azote amidique du composé amidique N-substitué (A) sont substitués par des groupes oxo, est inférieure ou égale à 550 ppm en masse.
PCT/JP2022/018477 2021-05-21 2022-04-21 Composition de décomposition/nettoyage, son procédé de production, et procédé de nettoyage de polymère adhésif WO2022244593A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020080060A1 (fr) * 2018-10-16 2020-04-23 昭和電工株式会社 Composition, procédé de nettoyage de polymère adhésif, procédé de production de tranche de dispositif, et procédé de régénération de tranche de support
WO2020148968A1 (fr) * 2019-01-15 2020-07-23 昭和電工株式会社 Composition de décomposition/nettoyage, procédé pour le nettoyage d'un polymère adhésif et procédé pour la production d'une tranche de dispositif
WO2020166702A1 (fr) * 2019-02-15 2020-08-20 日産化学株式会社 Composition d'agent de nettoyage et procédé de nettoyage
WO2021039274A1 (fr) * 2019-08-27 2021-03-04 昭和電工株式会社 Composition et procédé pour nettoyer un polymère adhésif

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020080060A1 (fr) * 2018-10-16 2020-04-23 昭和電工株式会社 Composition, procédé de nettoyage de polymère adhésif, procédé de production de tranche de dispositif, et procédé de régénération de tranche de support
WO2020148968A1 (fr) * 2019-01-15 2020-07-23 昭和電工株式会社 Composition de décomposition/nettoyage, procédé pour le nettoyage d'un polymère adhésif et procédé pour la production d'une tranche de dispositif
WO2020166702A1 (fr) * 2019-02-15 2020-08-20 日産化学株式会社 Composition d'agent de nettoyage et procédé de nettoyage
WO2021039274A1 (fr) * 2019-08-27 2021-03-04 昭和電工株式会社 Composition et procédé pour nettoyer un polymère adhésif

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