WO2024257814A1 - Liquide de nettoyage, procédé de nettoyage, et procédé de fabrication d'élément semi-conducteur - Google Patents

Liquide de nettoyage, procédé de nettoyage, et procédé de fabrication d'élément semi-conducteur Download PDF

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Publication number
WO2024257814A1
WO2024257814A1 PCT/JP2024/021389 JP2024021389W WO2024257814A1 WO 2024257814 A1 WO2024257814 A1 WO 2024257814A1 JP 2024021389 W JP2024021389 W JP 2024021389W WO 2024257814 A1 WO2024257814 A1 WO 2024257814A1
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Prior art keywords
cleaning solution
group
cleaning
solution according
acid
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PCT/JP2024/021389
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English (en)
Japanese (ja)
Inventor
紘明 岩本
歩 鈴木
暢介 瀬戸
愛姫子 大▲崎▼
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AGC Inc
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Asahi Glass Co Ltd
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Priority to JP2025527978A priority Critical patent/JPWO2024257814A1/ja
Priority to CN202480033606.7A priority patent/CN121153103A/zh
Publication of WO2024257814A1 publication Critical patent/WO2024257814A1/fr
Anticipated expiration legal-status Critical
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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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/08—Liquid soap, e.g. for dispensers; capsuled
    • 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
    • C11D7/02—Inorganic compounds
    • C11D7/04—Water-soluble compounds
    • C11D7/08—Acids
    • 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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P52/00—Grinding, lapping or polishing of wafers, substrates or parts of devices

Definitions

  • the present invention relates to a cleaning solution, a cleaning method, and a method for manufacturing semiconductor devices.
  • a method for manufacturing a semiconductor element is to sequentially form a conductive film, an insulating film, a resist film, etc. on a semiconductor substrate such as a silicon wafer, form a circuit pattern through processes such as lithography and etching, and then form an oxide film, followed by planarization through chemical mechanical polishing (CMP). Furthermore, a new layer may be stacked on the flat surface to form a multi-layer semiconductor element.
  • CMP chemical mechanical polishing
  • polishing is performed using a slurry-like polishing agent containing abrasive particles (also called abrasive grains).
  • abrasive particles also called abrasive grains.
  • cerium compound-containing particles are preferably used as the abrasive grains from the viewpoint of improving the polishing rate.
  • the surface of the semiconductor element may contain unnecessary components such as polishing agent components (e.g., abrasive grains and organic components such as polymers) and polishing debris, etc. Therefore, the semiconductor element after the CMP process is generally cleaned with a cleaning solution.
  • cerium compound-containing particles may be difficult to remove because they form bonds with the surfaces of silicon compound films such as silicon dioxide films and silicon nitride films during the CMP process, or may adhere strongly due to the attractive force of zeta potential under acidic conditions. Therefore, cleaning has traditionally been performed using strong chemicals such as diluted hydrofluoric acid and sulfuric acid/hydrogen peroxide, but development of cleaning solutions with better handling properties is underway.
  • Patent Document 1 discloses an aqueous cleaning liquid containing an inorganic acid containing a fluorine atom (excluding hydrogen fluoride) or a salt thereof. Furthermore, Patent Document 2 discloses a post-CMP cleaning composition containing a specific organic acid, a specific fluoride, a specific additive, and the like. Patent Documents 1 and 2 do not disclose an embodiment including a fluoropolymer having an acidic group.
  • This disclosure has been made in consideration of the above circumstances, and aims to provide a cleaning solution that can effectively remove abrasive grains and organic components adhering to an object to be cleaned, a cleaning method that uses the cleaning solution, and a method for manufacturing semiconductor elements.
  • a cleaning solution for removing abrasive grains comprising a fluoropolymer having an acidic group and water.
  • R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or a chlorine atom
  • R3 is a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, or a fluoromethyl group
  • R f1 is a linear or branched fluoroalkyl chain which may contain an etheric oxygen atom, Or, R 2 and R f1 are linked to each other to form a straight or branched fluoroalkyl
  • R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or a chlorine atom;
  • R3 is a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, or a fluoromethyl group;
  • R f1 is a linear or branched fluoroalkylene group which may contain an etheric oxygen atom, and when R f1 is a fluoroalkylene group which does not contain an etheric oxygen atom, it has 1 to 10 carbon atoms,
  • Z is -SO3H , -SO3Z1 , -CO2H , -CO2Z1 , -PO(OH) 2 , -PO3 ( OZ1 ) 2 , or OH, and Z1 is a cation.
  • the cleaning solution according to [17] above, wherein the exposed surface contains at least one material selected from the group consisting of silicon dioxide and silicon nitride.
  • the present disclosure provides a cleaning solution that can effectively remove abrasive grains and organic components adhering to an object to be cleaned, a cleaning method that uses the cleaning solution, and a method for manufacturing semiconductor devices.
  • fluoroalkylene chain refers to a group obtained by removing the required number of fluorine atoms and hydrogen atoms from a straight-chain, branched, or cyclic fluoroalkane.
  • a "divalent fluoroalkylene chain” refers to a group obtained by removing a total of two fluorine atoms and hydrogen atoms from a fluoroalkane, and is also called a "fluoroalkylene group.” The required number can be determined from the chemical formula.
  • the cleaning solution of the present disclosure is characterized by containing a fluoropolymer having an acidic group (hereinafter, sometimes simply referred to as "fluoropolymer”) and water.
  • fluoropolymer having an acidic group
  • the fluoropolymer having an acidic group appropriately controls the zeta potential, inhibits the adsorption or bonding between the object to be cleaned and the abrasive component, and makes it easier to peel off the abrasive grains and organic components attached to the object to be cleaned.
  • the fluoropolymer adsorbs to the peeled abrasive grain components and functions as a dispersant, preventing them from re-adhering to the surface of the object to be cleaned.
  • the abrasive components can be effectively removed from the surface of the object to be cleaned.
  • This cleaning solution can be suitably used for removing abrasive grains, and in particular, can effectively remove abrasive grains bonded or attached to the substrate surface after the CMP process.
  • the cleaning solution contains at least a fluoropolymer having an acidic group and water, and may further contain other components within the range in which the effects of the present invention are achieved. Each component that may be contained in the polishing agent will be described below.
  • the fluoropolymer having an acidic group used in the present cleaning solution is a polymer having at least one acidic group and at least one fluorine atom in the molecule.
  • the fluoropolymer is preferably one that becomes uniform in water and is preferably one that can be dispersed or dissolved in water.
  • the acidic group is a proton-donating group, and specific examples thereof include a sulfonic acid group, a carboxy group, a phosphoric acid group, and a hydroxy group, which may be in the form of a salt.
  • the proportion of fluorine atoms in the polymer represented by the following formula (I) is preferably 60% or more, more preferably 80% or more, and even more preferably substantially 100% (perfluoropolymer).
  • Formula (I): Percentage of fluorine atoms (%) (number of fluorine atoms)/ ⁇ (number of fluorine atoms)+(number of hydrogen atoms) ⁇ 100
  • the fluoropolymer may have at least one acidic group.
  • concentration of the acidic group in the polymer per unit mass represented by the following formula (II) is preferably 0.3 mmol/g or more, more preferably 0.8 mmol/g or more.
  • the upper limit is not particularly limited, but from the viewpoint of excellent handleability of the polymer, it is preferably 4.0 mmol/g or less.
  • the TQ value (volume flow rate value) of the fluoropolymer having sulfonic acid groups is preferably 200 to 300°C, more preferably 220 to 300°C, and particularly preferably 240 to 290°C. If the TQ value is equal to or greater than the lower limit of the above range, the fluoropolymer has a sufficient molecular weight to effectively disperse particles. If the TQ value is equal to or less than the upper limit of the above range, the solubility of the fluoropolymer is improved, allowing a homogeneous solution to be prepared as a cleaning liquid.
  • the TQ value is an index of the molecular weight of a fluoropolymer having a sulfonic acid group.
  • TQ value the temperature at which the extrusion rate becomes 100 mm 3 /sec when the above fluoropolymer is melt-extruded using a nozzle having a length of 1 mm and an inner diameter of 1 mm under an extrusion pressure of 2.94 MPa.
  • the number average molecular weight (Mn) of the fluoropolymer having a carboxylic acid group is preferably 1,000 or more, more preferably 1,500 or more, and particularly preferably 2,500 or more.
  • Mn of the fluoropolymer is preferably 1,000,000 or less, more preferably 900,000 or less, and particularly preferably 800,000 or less.
  • the Mn is a value determined by gel permeation chromatography (GPC) in terms of standard polystyrene.
  • the fluoropolymer preferably has a unit represented by the following formula (1) (also referred to as structural unit (1)) from the viewpoints of excellent cleanability, ability to prevent redeposition of abrasive grains, and solubility in water.
  • R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom, or a chlorine atom;
  • R3 is a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, or a fluoromethyl group;
  • R f1 is a linear or branched fluoroalkyl chain which may contain an etheric oxygen atom, Or, R 2 and R f1 are linked to each other to form a straight or branched fluoroalkyl chain which may contain an ether oxygen atom between carbon atoms;
  • R 3 and R f1 are linked to each other to form a linear or branched fluoroalkyl chain which may contain an ether oxygen atom between carbon atoms;
  • Z is -SO3H , -SO3Z1 , -CO2H , -CO2Z1 ,
  • R2 and R3 are not linked to Rf1 .
  • R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom or a chlorine atom. From the viewpoint of superior cleaning properties, a fluorine atom or a chlorine atom is preferred, and a fluorine atom is more preferred.
  • R3 is a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, or a fluoromethyl group. Examples of the fluoromethyl group include CH2F- , CHF2- , and CF3- , with CHF2- and CF3- being preferred, and CF3- (perfluoromethyl group) being more preferred.
  • a fluorine atom, a chlorine atom, or a fluoromethyl group is preferred, a fluorine atom or a fluoromethyl group is more preferred, and a fluorine atom is even more preferred.
  • R f1 is a linear or branched fluoroalkyl chain which may contain an ethereal oxygen atom.
  • the ethereal oxygen atom may be present between carbon atoms constituting R f1 , or the end bonded to CR 3 may be an ethereal oxygen atom, i.e., an oxyfluoroalkyl chain.
  • R f1 in the formula (1) when n is 1, that is, when one structural unit (1) contains one Z, will be described.
  • the linear or branched fluoroalkyl chain containing an etheric oxygen atom between carbon atoms in R f1 is a fluoroalkylene group.
  • the fluoroalkylene group include groups represented by the following formula (F1). -R f11 -(OR f11 ) m1 -*...(F1)
  • Each R f11 independently represents a linear or branched fluoroalkylene group having 1 to 6 carbon atoms; m1 represents an integer of 1 to 200; and * represents a bond to Z.
  • R f11 include -CF 2 -, -CHF-; -CF 2 CF 2 -, -CHFCF 2 -, -CHFCHF-, -CH 2 CF 2 -, -CH 2 CHF-; -CF 2 CF 2 CF 2 -, -CF 2 CHFCF 2 -, -CF 2 CH 2 CF 2 -, -CHFCF 2 CF 2 -, -CHFCHF 2 -, -CHFCHFCHF-, -CHFCH 2 CF 2 -, -CH 2 CF 2 CF 2 -, -CH 2 CHFCF 2 -, -CH 2 CHFCF 2 -, -CH 2 CHFCF-, -CH 2 CHFCHF-, -CH 2 CH 2 CHF-, -CH 2 CHFCHF-, -CH 2 CH 2 CHF-, -CF(CF 3 )CF 2 -, -CF(CHF 2 ) CF 2 -, -CF(
  • R f11 may be the same or different. From the viewpoint of superior cleaning properties, R f11 is preferably a perfluoroalkylene group. The number of carbon atoms in R f11 is preferably 1 to 4, and more preferably 2 to 3. m1 may be 1 to 200, and from the viewpoint of superior cleaning properties, it is preferably 1 to 150, and more preferably 1 to 120.
  • the linear or branched fluoroalkyl chain containing an etheric oxygen atom between carbon atoms in R f1 is an oxyfluoroalkylene group.
  • the oxyfluoroalkylene group include groups represented by the following formula (F2). -(OR f12 ) m2 -*...(F2)
  • Each R f12 independently represents a linear or branched fluoroalkylene group having 1 to 6 carbon atoms
  • m2 represents an integer of 1 to 200
  • * represents a bond to Z.
  • Specific examples and preferred embodiments of Rf12 are the same as those of Rf11 .
  • Specific examples and preferred embodiments of m2 are the same as those of m1.
  • the fluoroalkyl chain in R f1 that does not contain an etheric oxygen atom between carbon atoms includes a group represented by the following formula (F3). -(O) m3 -R f13 -*...(F3)
  • R f13 is a linear or branched fluoroalkylene group having 1 to 10 carbon atoms
  • m3 is 0 or 1
  • * is a bond to Z.
  • R f13 include, in addition to those listed for R f11 , -CF 2 CF 2 CF 2 CF 2 CF 2 CF 2 CF 2 -, -CF 2 CF 2 CF 2 CF 2 CF 2 CF 2 CF 2 -, -CF 2 CF 2 CF 2 CF 2 CF 2 CF 2 CF 2 -, -CF 2 CF 2 CF 2 CF 2 CF 2 CF 2 CF 2 -, -CF 2 CF 2 CF 2 CF 2 CF 2 CF 2 CF 2 - , etc.
  • the preferred number of carbon atoms for R f13 is 1 to 6, and the more preferred structure is the same as that for R f11 , with a perfluoroalkylene group being preferred.
  • R f1 in the formula (1) when n is 2, that is, when one structural unit (1) contains two Zs, will be described.
  • Examples of the linear or branched fluoroalkyl chain which may contain an etheric oxygen atom in R f1 include a group represented by the following formula (F4).
  • Each R f14 is independently a linear or branched fluoroalkylene group having 1 to 6 carbon atoms
  • R f15 is a linear or branched fluoroalkyl chain having 1 to 6 carbon atoms
  • each L 1 is independently a linear or branched fluoroalkylene group which may contain an etheric oxygen atom
  • m4 is 0 or 1
  • m5 is an integer of 0 to 200
  • * is a bond to Z.
  • Specific examples and preferred embodiments of R f14 are the same as those of R f11 .
  • R f15 include trivalent groups in which any one hydrogen atom or fluorine atom has been removed from the specific examples of R f11 .
  • m5 may be from 0 to 200, and from the viewpoint of superior cleaning properties, it is preferably from 0 to 150, and more preferably from 0 to 120.
  • L1 examples include groups represented by the following formula (L1). -(O) p1 -L f1 -(OL f2 ) p2 -*...(L1)
  • L f1 and L f2 each independently represent a linear or branched fluoroalkylene group having 1 to 6 carbon atoms; p1 is 0 or 1; p2 is an integer of 0 to 200; and * represents a bond to Z.
  • L f1 and L f2 are the same as those of R f11 , and a perfluoroalkylene group is preferred, provided that when p1 is 0, R f15 L 1 or R f15 L 12 preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms.
  • p2 may be an integer of 0 to 200, and is preferably an integer of 0 to 100, and more preferably an integer of 0 to 50, from the viewpoint of superior cleaning properties.
  • the fluoroalkyl chain in R f1 that does not contain an etheric oxygen atom between carbon atoms includes a group represented by the following formula (F5). -(O) m6 -R f16 -*...(F5)
  • R f16 is a linear or branched trivalent fluoroalkyl chain having 1 to 10 carbon atoms, m3 is 0 or 1, and * is a bond to Z.
  • Specific examples of R f16 include trivalent groups in which any one hydrogen atom or fluorine atom has been removed from the specific examples of R f13 .
  • R2 and Rf1 are linked together.
  • R 1 is a hydrogen atom, a fluorine atom or a chlorine atom, and from the viewpoint of cleaning properties, a fluorine atom or a chlorine atom is preferred, and a fluorine atom is more preferred.
  • R3 is a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, or a fluoromethyl group. From the viewpoint of cleaning properties, a fluorine atom, a chlorine atom, or a fluoromethyl group is preferable, a fluorine atom or a fluoromethyl group is more preferable, and a fluorine atom is even more preferable.
  • R f17 each independently represents a linear or branched fluoroalkylene group having 1 to 6 carbon atoms, m7 is 0 or 1, m8 is an integer of 0 to 50, m9 is 0 or 1, * is a bond on the CR1 side, and ** is a bond on the CR3 side.
  • R f17 are the same as those of R f11 , except that at least one of R f17 has a bond to Z, and the R f17 having the bond can be a residue obtained by removing one or two arbitrary hydrogen atoms or fluorine atoms from the specific examples of R f11 .
  • R f17 is preferably a perfluoroalkylene group.
  • m8 is an integer of 0 to 50, preferably 0 to 12, and more preferably 0 to 6.
  • R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom or a chlorine atom. From the viewpoint of cleaning properties, a fluorine atom or a chlorine atom is preferred, and a fluorine atom is more preferred.
  • R f18 each independently represents a linear or branched fluoroalkylene group having 1 to 6 carbon atoms, m10 is 0 or 1, m11 is an integer of 0 to 50, m12 is 0 or 1, * represents a bond on the CR1 side, and ** represents a bond on the CR3 side.
  • R f18 are the same as those of R f11 , except that at least one of R f18 has a bond to Z, and the R f18 having the bond can be a residue obtained by removing one or two arbitrary hydrogen atoms or fluorine atoms from the specific examples of R f11 .
  • R f18 is preferably a perfluoroalkylene group.
  • m11 is an integer of 0 to 50, preferably 0 to 12, and more preferably 0 to 6.
  • Z is -SO3H , -SO3Z1 , -CO2H , -CO2Z1, -PO3H, -PO3Z1, or OH, and Z1 is a cation.
  • Z1 include alkali metal ions such as sodium ion and potassium ion, and ammonium ions obtained by neutralization with ammonia or ethanolamine from the viewpoint of superior cleaning properties, with ammonium ions obtained by neutralization with ammonia or ethanolamine being preferred.
  • Z is preferably -SO3H , -SO3Z1 , -CO2H , or OH from the viewpoint of further improving cleaning properties and easiness of polymer synthesis.
  • each of the multiple symbols may be the same or different.
  • R 1 , R 2 and R 3 of the unit represented by formula (1) are all fluorine atoms.
  • the fluoroalkylene chain or oxyfluoroalkylene chain in R f1 is a perfluoroalkylene chain or an oxyperfluoroalkylene chain.
  • n is an integer of 1 to 200
  • the acidic group may be in the form of a salt.
  • the structural unit (1) preferably has (i) of embodiment (I), and is preferably a unit represented by the following formula (1A): -[CR 1 R 2 -CR 3 (R f1 -Z)] - ...
  • Z is -SO3H , -SO3Z1 , -CO2H , -CO2Z1 , -PO(OH) 2 , -PO3 ( OZ1 ) 2 , or OH, and Z1 is a cation.
  • the symbols in formula (1A) are the same as those in formula (1), and the preferred embodiments are also as described above, so that the explanation thereof will be omitted here.
  • the present fluoropolymer may be a polymer consisting only of units represented by formula (1), or may be a copolymer containing other structural units.
  • Examples of other structural units include the following structural units (11) to (13).
  • Structural unit (11) A structural unit having an acidic group and a fluorine atom, and having a structure different from that of formula (1)
  • Structural unit (12) A structural unit having a fluorine atom and no acidic group
  • Structural unit (13) A structural unit not having a fluorine atom
  • Examples of the structural unit (11) include units derived from monomers in which at least one hydrogen atom has been substituted with a fluorine atom in a monomer having a known acidic group, such as (meth)acrylic acid.
  • R 21 and R 22 each independently represent a hydrogen atom, a fluorine atom or a chlorine atom. From the viewpoint of cleaning properties, a fluorine atom or a chlorine atom is preferred, and a fluorine atom is more preferred.
  • R 23 is a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, or a fluoromethyl group. From the viewpoint of cleaning properties, a fluorine atom, a chlorine atom, or a fluoromethyl group is preferable, a fluorine atom or a fluoromethyl group is more preferable, and a fluorine atom is even more preferable.
  • Rf21 are the same as those of Rf11 .
  • Specific examples and preferred embodiments of m21 are the same as those of m1.
  • R25 is preferably a fluorine atom.
  • each R f22 independently represents a linear or branched fluoroalkylene group having 1 to 6 carbon atoms
  • m22 represents an integer of 1 to 200
  • R 26 represents a hydrogen atom or a fluorine atom.
  • Specific examples and preferred embodiments of Rf22 are the same as those of Rf11 .
  • Specific examples and preferred embodiments of m22 are the same as those of m1.
  • the fluoroalkyl group or oxyfluoroalkyl group not containing an etheric oxygen atom between carbon atoms in R 24 includes groups represented by the following formula (23). -(O) m23 -R f23 -R 27 ...(23)
  • R f23 is a linear or branched fluoroalkyl group having 1 to 10 carbon atoms
  • m23 is 0 or 1
  • R 27 is a hydrogen atom or a fluorine atom.
  • Specific examples and preferred embodiments of R f23 are the same as those of R f11 and R f13 .
  • each of the multiple symbols may be the same or different.
  • R 21 and R 22 of the unit represented by formula (12) are both fluorine atoms.
  • R 23 is preferably a fluorine atom or a fluoromethyl group, and more preferably a fluorine atom.
  • R 24 is preferably a fluorine atom, a linear or branched perfluoroalkyl group which may contain an etheric oxygen atom between the carbon-carbon atom, or a linear or branched oxyperfluoroalkyl group which may contain an etheric oxygen atom between the carbon-carbon atom, and more preferably a fluorine atom.
  • the structural unit (12) include the following: -CF 2 -CF 2 - -CF 2 -CF (OCF 2 CF 2 CF 3 )- -CF2- CF ⁇ OCF2CF ( CF3 ) OCF2CF3 ⁇ - -CF 2 -CF ⁇ OCF 2 CF (CF 3 )OCF 2 CF 2 CF 3 ⁇ - -CF2- CF[ CF2O ⁇ CF ( CF3 ) CF2O ⁇ nCF2 ( CF3 )]- -CF2 - CF ( OCF2CF2CF2OCF2CF3 ) - -CF2 - CF ( OCF2CF2OCF2CF3 ) - -CF 2 -CF (OCF 2 CF 2 CF 2 CF 3 )- -CF 2 -CF(OCF 3 )-
  • n is an integer from 1 to 200.
  • Examples of the structural unit (13) include structural units derived from known monomers that do not contain fluorine atoms.
  • monomers include vinyl monomers such as ethylene, vinyl chloride, vinylidene chloride, styrene, methylstyrene, vinyltoluene, and p-t-butylstyrene; (meth)acrylate monomers such as methyl (meth)acrylate, ethyl (meth)acrylate, and n-propyl (meth)acrylate; acrylamide monomers such as (meth)acrylamide, N,N-dimethyl (meth)acrylamide, and N,N-diethyl (meth)acrylamide; and (meth)acrylic acid.
  • vinyl monomers such as ethylene, vinyl chloride, vinylidene chloride, styrene, methylstyrene, vinyltoluene, and p-t-butylstyrene
  • (meth)acrylate monomers such
  • the fluoropolymer used in the present cleaning solution preferably contains the structural unit (1), more preferably the structural unit (1A), and from the viewpoints of improved cleaning properties and polymer handleability, it is preferred that the fluoropolymer further contains the structural unit (12).
  • the structural unit (12) is contained, the molar ratio of the structural unit (1) to the structural unit (12) is preferably from 5:95 to 60:40, more preferably from 10:90 to 50:50, and even more preferably from 15:85 to 40:60.
  • the structural unit (13) is preferably present in an amount of no more than 10 mol %, more preferably no more than 5 mol %, and even more preferably no more than 1 mol %, relative to all structural units constituting the fluoropolymer, and it is particularly preferable that the structural unit (13) is not present.
  • each constituent unit is not particularly limited, and may be a random copolymer or a block copolymer. From the viewpoint of excellent cleaning properties, a random copolymer is preferred.
  • the proportion of the fluoropolymer in the cleaning solution is preferably 0.001 to 30 mass% relative to the total amount of the cleaning solution, more preferably 0.005 to 20 mass%, and particularly preferably 0.01 to 10 mass%. Note that a cleaning solution containing a high concentration of the fluoropolymer may be prepared and then appropriately diluted at the time of use.
  • the synthesis method of the fluoropolymer is not particularly limited.
  • the following monomer (1a) corresponding to the structural unit (1) and the following monomer (12a) corresponding to the structural unit (12) may be mixed, and an initiator may be further added to polymerize the mixture by a known polymerization method such as solution polymerization, bulk polymerization, or various radical polymerizations. Solution polymerization is preferred in terms of ease of adjusting the number average molecular weight of the polymer.
  • a block of the structural unit (1) may be synthesized first, and the monomer (12a) may be polymerized to the block of the structural unit (1), or the order of synthesis may be reversed in the production method.
  • the block of the structural unit (1) and the block of the structural unit (12) may be synthesized separately, and then the block of the structural unit (1) and the block of the structural unit (12) may be coupled.
  • CR 1 R 2 CR 3 ⁇ R f1 - (Z) n ⁇ ...(1a)
  • CR21R22 CR23R24 ... ( 12a )
  • the symbols in the formula are as defined above.
  • the cleaning solution may further contain other components, such as a reducing compound, a complexing agent, a heterocyclic aromatic compound, an acidic compound, a preservative, a rust inhibitor, a surfactant, a basic compound, and a water-soluble organic solvent.
  • the cleaning solution may contain a reducing compound that, for example, reduces cerium ( CeO4 ) bonded to silicon oxide on the surface to be cleaned to water-soluble Ce3 + , making it easier to remove from the surface to be cleaned and improving the cleaning effect.
  • the reducing compound can be appropriately selected from those having a reducing effect on the abrasive grain components.
  • the reducing compound is preferably gallic acid or its salt, gallic acid ester, pyrogallol, catechol, resorcinol, thiosulfuric acid or its salt, dithioic acid or its salt, ascorbic acid, uric acid, diphosphorous acid or its salt, oxalic acid or its salt, hydrogen peroxide, or hydroquinone.
  • the proportion of the reducing compound in the cleaning solution is preferably 0.001% by mass to 30% by mass, more preferably 0.005% by mass to 20% by mass, and even more preferably 0.01% by mass to 10% by mass, based on the total amount of the cleaning solution.
  • the cleaning solution may contain a complexing agent.
  • the complexing agent can be appropriately selected from among those that form complexes with the metal components in the abrasive grains and the metal components in the residues derived from the substrate generated by polishing.
  • the complexing agent is preferably an organic compound having a molecular weight of 1,000 g/mol or less and having two or more substituents selected from a carboxyl group, an amino group, a phosphoryl group, a sulfonic acid group, and a hydroxyl group in the molecule.
  • the complexing agent may be tetramethylethylenediamine (TMEDA), ethylenediaminetetraacetic acid (EDTA), N-hydroxyethylethylenediaminetriacetic acid (NHEDTA), nitrilotriacetic acid (NTA), diethylenetriaminepentaacetic acid (DPTA), ethanol diglycinate, citric acid, malic acid, gluconic acid, oxalic acid, phosphoric acid, tartaric acid, malonic acid, succinic acid, dimercaptosuccinic acid, glutaric acid, maleic acid, phthalic acid, fumaric acid, methyldiphosphonic acid, aminotrismethylenephosphonic acid, ethylidene-diphosphonic acid, 1-methyl-2-methyl-2-propanediol ...
  • TEDA tetramethylethylenediamine
  • EDTA ethylenediaminetetraacetic acid
  • NHEDTA N-hydroxyethylethylenediaminetriace
  • 1,1-hydroxyethane-1,1-diphosphonic acid HEDP
  • 1-hydroxypropylidene-1,1-diphosphonic acid ethylaminobismethylenephosphonic acid
  • dodecylaminobismethylenephosphonic acid nitrilotrismethylenephosphonic acid
  • ethylenediaminebismethylenephosphonic acid ethylenediaminetetrakismethylenephosphonic acid, hexadiaminetetrakismethylenephosphonic acid, diethylenetriaminepentamethylenephosphonic acid, and 1,2-propanediaminepentamethylenephosphonic acid or ammonium salts.
  • the content of the complexing agent in the cleaning solution is preferably 0.01 to 30% by mass, more preferably 0.05 to 20% by mass, and still more preferably 0.1 to 10% by mass, based on the total amount of the cleaning solution.
  • the cleaning solution may contain a heterocyclic aromatic compound.
  • the cleaning solution containing the heterocyclic aromatic compound is less susceptible to deterioration of quality due to microorganisms and the like, and can provide a more excellent cleaning effect.
  • the heterocyclic aromatic compound include imidazole compounds, pyrazole compounds, thiazole compounds, and triazole compounds.
  • the imidazole compounds include imidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 1-benzyl-2-methylimidazole, and 1-benzyl-2-phenylimidazole.
  • Examples of the pyrazole compounds include pyrazole, 3-methylpyrazole, and 3,5-dimethylpyrazole.
  • Examples of the thiazole compounds include benzisothiazoline, isothiazolin, 1,2-benzisothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-(thiocyanomethylthio)benzthiazole, 2-mercaptobenzthiazole, and 3-allyloxy-1,2-benzisothiazole-1,1-oxide.
  • Examples of the triazole compounds include 1H-benzotriazole, 4-methyl-1H-benzotriazole, and 5-methyl-1H-benzotriazole.
  • the content of the heterocyclic aromatic compound in the cleaning solution is preferably 0.01 to 30 mass %, more preferably 0.05 to 20 mass %, and particularly preferably 0.1 to 10 mass %, based on the total amount of the cleaning solution.
  • the cleaning solution may contain a surfactant, which may be ionic or nonionic.
  • Surfactants include salts containing suitable hydrophobic groups such as alkyl carboxylates, alkyl polyacrylates, alkyl sulfates, alkyl phosphates, alkyl bicarboxylates, alkyl bisulfates, alkyl biphosphates, substituted aryl carboxylates, substituted aryl sulfates, substituted aryl phosphates, substituted aryl bicarboxylates, substituted aryl bisulfates, substituted aryl biphosphates, long chain alcohols, ethoxylated alcohols, ethoxylated acetylenic diol surfactants, polyethylene glycol alkyl ethers, propylene glycol alkyl ethers, glucoside alkyl ethers, polyethylene glycol octylphenyl ethers, polyethylene glycol alkyl
  • the cleaning solution may contain an acidic compound other than the fluoropolymer having an acidic group.
  • the acidic compound is used for the purpose of adjusting the pH, etc.
  • inorganic acids such as nitric acid, sulfuric acid, hydrochloric acid, phosphoric acid, and condensed phosphoric acid are preferable.
  • the cleaning solution may contain a basic compound for the purpose of adjusting the pH, etc.
  • the basic compound include monoethanolamine (MEA), diethanolamine, triethanolamine (TMA), morpholine, isopropylamine, hydroxylamine, diisopropanolamine, diglycolamine, triethylamine, N-methylmorpholine, methylethanolamine, N-aminopropylmorpholine, and 3-amino-propanol, tetramethylammonium hydroxide (TMAH), ammonium hydroxide, tetraethylammonium hydroxide (TEAH), tetrapropylammonium hydroxide (TPAH), tetrabutylammonium hydroxide (TBAH), tributylmethylammonium hydroxide (TBMAH), benzyltrimethylammonium hydroxide (BTMAH), choline, choline hydroxide, ethyltrimethylammonium hydroxide, ethy
  • the cleaning performance of this cleaning solution can be improved by adjusting the pH to within the range of 1 to 12.
  • the pH is preferably 7 or less, and more preferably 1 to 5, in order to further improve cleaning performance.
  • the pH is preferably 7 or more, and more preferably 8 to 12, in order to further improve cleaning performance.
  • the cleaning solution may contain a water-soluble organic solvent.
  • the water-soluble organic solvent include propylene glycol (PG), glycol ether, and aprotic solvents.
  • examples of the aprotic solvent include N-methylpyrrolidone (NMP), dimethylsulfoxide (DMSO), dimethylacetamide (DMAC), sulfolane, and dimethylformamide (DMF).
  • the water-soluble organic solvent may be a mixed solvent of two or more kinds.
  • This cleaning liquid is suitable as a cleaning liquid for removing abrasive grains from a surface to be cleaned, and can also effectively remove organic components such as polymers contained in the abrasive.
  • the surface to be cleaned may be an exposed surface (surface) of a semiconductor substrate, and the exposed surface may include a silicon dioxide surface and/or a silicon nitride surface.
  • the surface to be cleaned may be an exposed surface that has been polished using an abrasive containing abrasive grains. Examples of the abrasive grains include silica particles, alumina particles, zirconia particles, titania particles, germania particles, and cerium compound-containing particles.
  • the present cleaning solution is particularly suitable for cerium compound-containing particles such as ceria particles and cerium hydroxide particles.
  • the present cleaning solution can also be suitably used for fine abrasive grains, and exhibits excellent cleaning effects even for abrasive grains having an average particle size of 300 nm or less, for example.
  • the cleaning target for which this cleaning solution exhibits particularly excellent effects is a semiconductor substrate after CMP processing using an abrasive containing cerium compound-containing particles as abrasive grains, and which includes an exposed surface on which an oxide film, nitride film, etc. remain. Cerium particles adsorbed or bonded to the oxide film, etc. remain on the exposed surface, and this cleaning solution can suitably remove these particles.
  • the cleaning method of the present disclosure includes cleaning the surface to be cleaned using the above-mentioned cleaning liquid.
  • cleaning liquid is supplied to the surface to be cleaned such as a semiconductor substrate while a cleaning member such as a pad or brush is physically brought into contact with the surface to be cleaned to remove abrasive grains
  • immersion cleaning in which an object to be cleaned including the surface to be cleaned is immersed in the cleaning liquid
  • spin-drop cleaning in which the cleaning liquid is dropped onto the object to be cleaned while rotating it
  • spray cleaning in which the cleaning liquid is sprayed.
  • ultrasonic treatment may be performed on the cleaning liquid.
  • the above-mentioned cleaning process may be performed only once, or may be performed two or more times.
  • the temperature of the cleaning liquid may be appropriately adjusted in consideration of the heat resistance of the object to be cleaned, etc.
  • the temperature of the cleaning liquid may be appropriately adjusted within the range of, for example, 10 to 60°C, and preferably 15 to 50°C.
  • the cleaning time may be appropriately adjusted within the range of 10 seconds to 5 minutes, and is preferably 20 seconds to 3 minutes.
  • the present disclosure further provides a semiconductor element obtained by the above cleaning method.
  • the semiconductor element obtained by the above cleaning method has a clean surface with few abrasive grains or polishing residues.
  • the present invention will be specifically explained below with reference to examples and comparative examples, but the present invention is not limited to these examples.
  • the room temperature is 20 to 25°C.
  • Examples 1 to 15 are examples, and Examples 16 to 19 are comparative examples.
  • evaluation items and evaluation methods are as follows. ⁇ pH> While stirring with a magnetic stirrer, the pH of the cleaning solution was measured with a commercially available pH meter, using a pH meter "F-2000PI-S” and a Tou pH electrode "9615S-10D” manufactured by Horiba, Ltd.
  • ⁇ Cerium oxide and organic component removal performance> (Preparation of polished substrate) A commercially available slurry-like abrasive (polishing slurry) containing cerium oxide particles having an average particle size of 300 nm or less, an organic component such as a polymer, a surfactant, and water was prepared. One surface of the quartz glass plate was polished for 30 seconds using a commercially available CMP device and the above-mentioned abrasive. A "FAM12B" manufactured by SpeedFam was used as the CMP device. A hard urethane pad was used as the polishing pad.
  • polishing pressure was 14 kPa
  • the platen rotation speed was 40 rpm
  • 30 cc of chemical solution was poured per minute to perform polishing for 5 minutes. Polishing was performed under the above conditions, and the substrate was rinsed several times with pure water and then submerged and stored to obtain a ceria-contaminated substrate.
  • the obtained ceria-contaminated SiO2 substrate was subjected to PVA disk sponge cleaning (rotation speed 300 rpm, substrate conveying speed 12.5 mm/s, cleaning process using 5 ml of cleaning solution was performed twice for each substrate). After rinsing with pure water several times, the substrate was dried to obtain a substrate after cleaning.
  • the polished substrate after the above treatment is referred to as "polished substrate after post-cleaning”.
  • Fluoropolymer 1 A binary water-soluble fluorocopolymer containing a tetrafluoroethylene (-CF 2 CF 2 -) structure and a SO 3 H group-containing fluoroalkylene (-CF 2 CF(OCF 2 CF(CF 3 )OCF 2 CF 2 SO 3 H)-) structure in a molar ratio of 73:27.
  • the concentration of acidic groups per unit mass is 1.40 mmol/g.
  • Fluoropolymer 2 a binary water-soluble fluorocopolymer containing the above monomer unit structures in a molar ratio of 78:22.
  • the concentration of acidic groups per unit mass is 1.25 mmol/g.
  • Fluoropolymer 3 a binary water-soluble polymer containing the above monomer unit structures in a molar ratio of 82:18.
  • the concentration of acidic groups per unit mass is 1.10 mmol/g.
  • Fluoropolymer 4 A water-soluble fluorine homopolymer formed only of a CO 2 H group-containing fluoroalkylene (-CF 2 CF(OCF 2 CF 2 CF 2 CO 2 H)-) structure.
  • the concentration of acidic groups per unit mass was 3.42 mmol/g.
  • Fluoropolymer 5 A water-soluble fluorine homopolymer formed solely of a CO 2 H group-containing fluoroalkylene (-CF 2 CF(OCF 2 CF(CF 3 )OCF 2 CF 2 CO 2 H)-) structure. The concentration of acidic groups per unit mass is 2.45 mmol/g. Polyacrylic acid (water-soluble polymer for comparison): purity 100% by mass, reagent.
  • ⁇ pH Adjuster> Inorganic acid compounds 0.1N HNO 3 aq.: 0.1N nitric acid aqueous solution, reagent. 0.1N polyphosphoric acid aq.: 0.1N condensed phosphoric acid (P(O)(OH)O) n , reagent. (Basic Compound) 0.1N triethanolamine aq.: 0.1N triethanolamine aqueous solution, reagent.
  • Citric acid 100% purity by mass, reagent.
  • HEDP 1-hydroxyethylidene-1,1-diphosphonic acid, purity 60% by mass, manufactured by Chelest Corporation "Chelest PH-210".
  • Example 1 At room temperature, 0.2 g of fluoropolymer 1 and 0.3 g of 0.075% KB-838 were added to 99.5% ultrapure water and mixed with stirring to prepare a cleaning liquid. The total concentration of the pH adjuster, reducing compound, organic acid compound, and heterocyclic aromatic compound was determined as the amount of active ingredients (total content of active ingredients, total concentration of active ingredients). The total concentration of the active ingredients was 0.20 mass%. The pH of the cleaning solution was 3.00. The compounding compositions and the evaluation results are shown in Table 1.
  • Examples 2 to 19 A cleaning solution was prepared in the same manner as in Example 1, except that the blending composition was changed to that shown in Table 1. The blending composition and the evaluation results are shown in Table 1.
  • the cleaning solution disclosed herein can be used, for example, as a cleaning solution for abrasives used in CMP, and contributes to improving the production efficiency of semiconductor elements.

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Abstract

L'invention fournit un liquide de nettoyage permettant de retirer efficacement des grains abrasifs et des composants organiques en adhésion sur un objet à nettoyer, un procédé de nettoyage mettant en œuvre ledit liquide de nettoyage, et un procédé de fabrication d'élément semi-conducteur.　Plus précisément, l'invention concerne un liquide de nettoyage pour retrait de grains abrasifs qui contient un polymère fluoré possédant un groupe acide, et une eau.
PCT/JP2024/021389 2023-06-14 2024-06-12 Liquide de nettoyage, procédé de nettoyage, et procédé de fabrication d'élément semi-conducteur Ceased WO2024257814A1 (fr)

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Citations (5)

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Publication number Priority date Publication date Assignee Title
JP2016138282A (ja) * 2007-05-17 2016-08-04 アドバンスド テクノロジー マテリアルズ，インコーポレイテッド Ｃｍｐ後洗浄配合物用の新規な酸化防止剤
JP2017536332A (ja) * 2014-09-23 2017-12-07 スリーエム イノベイティブ プロパティズ カンパニー 窒素含有ハイドロフルオロエーテル及びその使用方法
WO2019181435A1 (fr) * 2018-03-22 2019-09-26 富士フイルム株式会社 Dispositif de filtration, dispositif de purification, et procédé de fabrication de médicament liquide
JP2020004968A (ja) * 2018-06-26 2020-01-09 バーサム マテリアルズ ユーエス，リミティド ライアビリティ カンパニー ポスト化学機械平坦化（ｃｍｐ）洗浄
WO2023095806A1 (fr) * 2021-11-25 2023-06-01 Ａｇｃ株式会社 Composé, composition, agent de traitement de surface, liquide de revêtement, article et procédé de fabrication d'un article

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016138282A (ja) * 2007-05-17 2016-08-04 アドバンスド テクノロジー マテリアルズ，インコーポレイテッド Ｃｍｐ後洗浄配合物用の新規な酸化防止剤
JP2017536332A (ja) * 2014-09-23 2017-12-07 スリーエム イノベイティブ プロパティズ カンパニー 窒素含有ハイドロフルオロエーテル及びその使用方法
WO2019181435A1 (fr) * 2018-03-22 2019-09-26 富士フイルム株式会社 Dispositif de filtration, dispositif de purification, et procédé de fabrication de médicament liquide
JP2020004968A (ja) * 2018-06-26 2020-01-09 バーサム マテリアルズ ユーエス，リミティド ライアビリティ カンパニー ポスト化学機械平坦化（ｃｍｐ）洗浄
JP2022009467A (ja) * 2018-06-26 2022-01-14 バーサム マテリアルズ ユーエス，リミティド ライアビリティ カンパニー ポスト化学機械平坦化（ｃｍｐ）洗浄
WO2023095806A1 (fr) * 2021-11-25 2023-06-01 Ａｇｃ株式会社 Composé, composition, agent de traitement de surface, liquide de revêtement, article et procédé de fabrication d'un article

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