CN113430069A - Low-hydroxylamine water-based cleaning solution, and preparation method and application thereof - Google Patents

Low-hydroxylamine water-based cleaning solution, and preparation method and application thereof Download PDF

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CN113430069A
CN113430069A CN202010209649.XA CN202010209649A CN113430069A CN 113430069 A CN113430069 A CN 113430069A CN 202010209649 A CN202010209649 A CN 202010209649A CN 113430069 A CN113430069 A CN 113430069A
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hydroxylamine
cyclodextrin
alkyl ether
alkylene glycol
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王溯
蒋闯
冯强强
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Shanghai Xinyang Semiconductor Material Co Ltd
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Shanghai Xinyang Semiconductor Material Co Ltd
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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
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    • C—CHEMISTRY; METALLURGY
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    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/046—Salts
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    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2065—Polyhydric alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/225—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin etherified, e.g. CMC
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; Quaternized amines
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02041—Cleaning
    • H01L21/02057—Cleaning during device manufacture
    • H01L21/02068—Cleaning during device manufacture during, before or after processing of conductive layers, e.g. polysilicon or amorphous silicon layers
    • H01L21/02071—Cleaning during device manufacture during, before or after processing of conductive layers, e.g. polysilicon or amorphous silicon layers the processing being a delineation, e.g. RIE, of conductive layers
    • 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
    • H01L21/02082—Cleaning product to be cleaned
    • 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
    • H01L21/70—Manufacture or treatment of devices consisting of a plurality of solid state components formed in or on a common substrate or of parts thereof; Manufacture of integrated circuit devices or of parts thereof
    • H01L21/71—Manufacture of specific parts of devices defined in group H01L21/70
    • H01L21/768—Applying interconnections to be used for carrying current between separate components within a device comprising conductors and dielectrics
    • H01L21/76838—Applying interconnections to be used for carrying current between separate components within a device comprising conductors and dielectrics characterised by the formation and the after-treatment of the conductors
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    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
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    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
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Abstract

The invention discloses a low-hydroxylamine water-based cleaning solution, a preparation method and application thereof. The invention provides a low-hydroxylamine water-based cleaning solution which is characterized by being prepared from the following raw materials in parts by mass: 0.1-5% of hydroxylamine compound, 0.5-20% of alcohol amine, 0.1-20% of quaternary ammonium base, 0.01-30% of chelating agent, 0.1-20% of polyquaternary ammonium salt surfactant, 0.1-15% of nonionic surfactant, 0.1-25% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials. The low-hydroxylamine water-based cleaning solution disclosed by the invention has strong corrosion inhibition on various metals and dielectrics and good cleaning effect.

Description

Low-hydroxylamine water-based cleaning solution, and preparation method and application thereof
Technical Field
The invention relates to a low-hydroxylamine water-based cleaning solution, a preparation method and application thereof.
Background
In the chip manufacturing technology, the cleaning solution of residues after the aluminum interconnection plasma etching is mainly hydroxylamine cleaning solution. With the continuous advance of technology nodes, more and more materials are introduced, such as metal materials of titanium, tungsten, titanium nitride, and the like, and low-k dielectric materials, and the compatibility of the conventional hydroxylamine cleaning solution with various materials is challenged. The development of hydroxylamine cleaning solutions with high compatibility is a problem to be solved in the art.
Disclosure of Invention
The invention provides a low-hydroxylamine water-based cleaning solution, a preparation method and application thereof, aiming at overcoming the defect of poor compatibility of the existing hydroxylamine cleaning solution to various metals and dielectric materials. The low-hydroxylamine water-based cleaning solution disclosed by the invention has strong corrosion inhibition on various metals and dielectrics and good cleaning effect.
The present invention solves the above technical problems by the following technical solutions.
The invention provides a low-hydroxylamine water-based cleaning solution which is prepared from the following raw materials in parts by mass: 0.1-5% of hydroxylamine compound, 0.5-20% of alcohol amine, 0.1-20% of quaternary ammonium base, 0.01-30% of chelating agent, 0.1-20% of polyquaternary ammonium salt surfactant, 0.1-15% of nonionic surfactant, 0.1-25% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials;
wherein the polyquaternium surfactant is polyquaternium-16;
the nonionic surfactant is one or more of EO-PO polymer L42, EO-PO polymer L43 and EO-PO polymer L44.
In the low-hydroxylamine water-based cleaning solution, the hydroxylamine compound can be one or more of hydroxylamine, N-methyl hydroxylamine, N-ethyl hydroxylamine, N-diethyl hydroxylamine, hydroxylamine sulfate, hydroxylamine nitrate, hydroxylamine phosphate, hydroxylamine chloride, hydroxylamine oxalate and hydroxylamine citrate, and hydroxylamine is preferred.
In the low hydroxylamine water-based cleaning solution, the mass fraction of the hydroxylamine compound can be 0.5-5%, preferably 1-5% (such as 1%, 2%, 5%), and the mass fraction is the mass percentage of the hydroxylamine compound in the total mass of the raw materials.
In the low hydroxylamine water-based cleaning solution, the alcohol amine may be an alcohol amine conventionally used in the art, preferably one or more of monoethanolamine, diethanolamine, triethanolamine, 2-aminoethanol, 1-amino-2-propanol, 1-amino-3-propanol, 2- (2-aminoethoxy) ethanol, 2- (2-aminoethylamino) ethylamine, trimethanolamine, diglycolamine, dilanolamine, n-propanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine and diethanomonoisopropanolamine, more preferably one or more of monoethanolamine, triethanolamine, diglycolamine and isopropanolamine.
In the low-hydroxylamine water-based cleaning solution, the mass fraction of the alcohol amine can be 1-10%, preferably 5-7% (such as 5%, 6%, 7%), and the mass fraction is the percentage of the mass of the alcohol amine in the total mass of the raw materials.
In the low hydroxylamine aqueous cleaning solution, the quaternary ammonium hydroxide may be one conventionally used in the art, preferably tetramethylammonium hydroxide (TMAH), trimethyl-2-hydroxyethylammonium hydroxide (choline), trimethyl-3-hydroxypropylammonium hydroxide, trimethyl-3-hydroxybutylammonium hydroxide, trimethyl-4-hydroxybutylammonium hydroxide, triethyl-2-hydroxyethylammonium hydroxide, tripropyl-2-hydroxyethylammonium hydroxide, tributyl-2-hydroxyethylammonium hydroxide, dimethylethyl-2-hydroxyethylammonium hydroxide, dimethylbis- (2-hydroxyethyl) ammonium hydroxide, monomethyltriethanolamine hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, ammonium hydroxide, ammonium hydroxide, ammonium salt, ammonium hydroxide, ammonium salt, ammonium salt, or the salt, One or more of tetraethylammonium hydroxide, monomethyltriethylammonium hydroxide, monomethyltripropylammonium hydroxide, monomethyltributylammonium hydroxide, monoethyltrimethylammonium hydroxide, monoethyltributylammonium hydroxide, dimethyldiethylammonium hydroxide, dimethyldibutylammonium hydroxide and benzyltrimethylammonium hydroxide, more preferably tetramethylammonium hydroxide and/or choline.
In the low hydroxylamine water-based cleaning solution, the mass fraction of the quaternary ammonium hydroxide can be 1% to 10%, preferably 5% to 10% (e.g., 5%, 7.5%, 10%), and the mass fraction is the percentage of the mass of the quaternary ammonium hydroxide in the total mass of the raw materials.
In the low hydroxylamine water-based cleaning solution, the chelating agent may be a chelating agent conventionally used in the art, preferably catechol (catechol), pyrogallol, gallic acid, alkyl gallate (e.g., methyl gallate and/or propyl gallate), alkyl catechol (e.g., one or more of methyl catechol, ethyl catechol, and tert-butyl catechol), one or more of malonic acid, maleic acid, and tartaric acid, more preferably one or more of gallic acid, malonic acid, and tartaric acid.
In the low hydroxylamine water-based cleaning solution, the mass fraction of the chelating agent can be 1-10%, preferably 5-10% (such as 5%, 6%, 10%), and the mass fraction is the percentage of the mass of the chelating agent in the total mass of the raw materials.
In the low-hydroxylamine water-based cleaning solution, the mass fraction of the polyquaternium surfactant can be 0.5-5%, preferably 1-2% (such as 1%, 1.5% and 2%), and the mass fraction is the mass percentage of the polyquaternium surfactant in the total mass of the raw materials.
In the low hydroxylamine water-based cleaning solution, the non-ionic surfactant is preferably EO-PO polymer L42.
In the low hydroxylamine water-based cleaning solution, the mass fraction of the nonionic surfactant can be 1% to 5%, preferably 1% to 2% (e.g., 1% or 2%), and the mass fraction is the mass percentage of the nonionic surfactant to the total mass of the raw materials.
In the low hydroxylamine water-based cleaning solution, the preparation method of the cyclodextrin modified alkylene glycol alkyl ether compound can be a conventional method for preparing the compound in the field, and refer to patent application CN 107765514A. The cyclodextrin modified alkylene glycol alkyl ether compound can be prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, and comprises the following steps:
(1) reacting a mixed solution of an alkylene glycol alkyl ether compound, maleic anhydride and a solvent to obtain a substance A;
(2) and (2) reacting the substance A obtained in the step (1), cyclodextrin and p-toluenesulfonic acid in a solvent to obtain the compound.
Wherein the cyclodextrin can be one or more of alpha-cyclodextrin, beta-cyclodextrin and gamma-cyclodextrin, and beta-cyclodextrin is preferred.
The alkylene glycol alkyl ether compound can be one or more of monoalkylene glycol monoalkyl ether, dialkylene glycol monoalkyl ether and trialkylene glycol monoalkyl ether, preferably monoalkylene glycol monoalkyl ether and/or dialkylene glycol monoalkyl ether, and more preferably ethylene glycol monobutyl ether and/or diethylene glycol monobutyl ether. The monoalkylene glycol monoalkyl ether is preferably one or more of ethylene glycol monobutyl ether, ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; the dialkylene glycol monoalkyl ether is preferably diethylene glycol monobutyl ether and/or diethylene glycol monomethyl ether; the said trialkyl glycol monoalkyl ether is preferably one or more of triethylene glycol monobutyl ether, triethylene glycol monoether, triethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether and tripropylene glycol monomethyl ether.
In the step (1), the feeding molar ratio of the alkylene glycol alkyl ether compound to the maleic anhydride can be the feeding molar ratio which is conventional in the field, and is preferably 1.01-1.05: 1;
in step (1), the solvent may be a solvent conventional in the art, and is preferably an aromatic hydrocarbon solvent (e.g., toluene).
In step (1), the temperature of the reaction may be a temperature conventional in the art, and is preferably 80 ℃ to 100 ℃ (e.g., 90 ℃).
In step (1), the reaction time may be a time conventional in the art, and is preferably 8 to 12 hours.
In the step (2), the feeding molar ratio of the substance A and the cyclodextrin can be the conventional feeding molar ratio in the field, and is preferably 1:1.2-1:1.
In the step (2), the mass of the p-toluenesulfonic acid can be conventional in the field, and is preferably 0.01-1% of the total mass of the substance A and the cyclodextrin.
In step (2), the solvent may be a solvent conventional in the art, and is preferably an aromatic hydrocarbon solvent (e.g., toluene).
In step (2), the temperature of the reaction may be a temperature conventional in the art, and is preferably 120 ℃ to 140 ℃ (e.g., 130 ℃).
In step (2), the reaction time may be a time conventional in the art, and is preferably 32 to 38 hours (e.g., 36 hours).
In the low-hydroxylamine water-based cleaning solution, the mass fraction of the cyclodextrin modified alkylene glycol alkyl ether compound can be 0.5-10%, preferably 1-5% (such as 1%, 2%, 5%), and the mass fraction is the mass percentage of the cyclodextrin modified alkylene glycol alkyl ether compound in the total mass of the raw materials.
In the low hydroxylamine water-based cleaning solution, the water is preferably one or more of deionized water, pure water and ultrapure water, and is more preferably deionized water.
In certain preferred embodiments of the present invention, the low hydroxylamine water-based cleaning solution is prepared from the following raw materials, wherein the raw materials comprise the following components in percentage by mass: 0.5-5% of hydroxylamine compound, 1-10% of alcohol amine, 1-10% of quaternary ammonium base, 1-10% of chelating agent, 0.5-5% of polyquaternary ammonium salt surfactant, 1-5% of nonionic surfactant, 0.5-10% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials.
In certain preferred embodiments of the present invention, the low hydroxylamine water-based cleaning solution is prepared from the following raw materials, wherein the raw materials comprise the following components in percentage by mass: 1-5% of hydroxylamine compound, 5-7% of alcohol amine, 5-10% of quaternary ammonium base, 5-10% of chelating agent, 1-2% of polyquaternary ammonium salt surfactant, 1-2% of nonionic surfactant, 1-5% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials.
In certain preferred embodiments of the present invention, the low hydroxylamine water-based cleaning solution is prepared from the following raw materials, wherein the raw materials comprise the following components in percentage by mass: 0.1-5% of hydroxylamine compound, 0.5-20% of alcohol amine, 0.1-20% of quaternary ammonium base, 0.01-30% of chelating agent, 0.1-20% of polyquaternary ammonium salt surfactant, 0.1-15% of nonionic surfactant, 0.1-25% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials.
In certain preferred embodiments of the present invention, the low hydroxylamine water-based cleaning solution is prepared from the following raw materials, wherein the raw materials comprise the following components in percentage by mass: 0.5-5% of hydroxylamine compound, 1-10% of alcohol amine, 1-10% of quaternary ammonium base, 1-10% of chelating agent, 0.5-5% of polyquaternary ammonium salt surfactant, 1-5% of nonionic surfactant, 0.5-10% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials.
In certain preferred embodiments of the present invention, the low hydroxylamine water-based cleaning solution is prepared from the following raw materials, wherein the raw materials comprise the following components in percentage by mass: 1-5% of hydroxylamine compound, 5-7% of alcohol amine, 5-10% of quaternary ammonium base, 5-10% of chelating agent, 1-2% of polyquaternary ammonium salt surfactant, 1-2% of nonionic surfactant, 1-5% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials.
The invention also provides a preparation method of the low hydroxylamine water-based cleaning solution, which comprises the following steps: and mixing the raw materials to obtain the low hydroxylamine water-based cleaning solution.
Wherein, the solid component in the raw material components is preferably added into the liquid component and stirred uniformly.
Wherein the temperature of the mixing may be room temperature.
The invention also provides application of the low hydroxylamine water-based cleaning solution in cleaning a semiconductor device after plasma etching.
Wherein, the substrate of plasma etching is preferably an aluminum interconnection substrate.
Wherein the temperature of the washing can be 60 ℃ to 75 ℃ (for example 75 ℃). The washing time may be 5min to 30min (e.g., 20 min).
In the present invention, the term "alkyl" refers to a straight or branched chain alkyl group having the specified number of carbon atoms. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like.
In the present invention, the term "hydroxylamine compounds" means compounds containing a fragment
Figure BDA0002422380640000061
A class of compounds of (1).
In the present invention, "room temperature" means 10 to 40 ℃ unless otherwise specified.
On the basis of the common knowledge in the field, the above preferred conditions can be combined randomly to obtain the preferred embodiments of the invention.
The reagents and starting materials used in the present invention are commercially available.
The positive progress effects of the invention are as follows: the low-hydroxylamine water-based cleaning solution disclosed by the invention has a low corrosion rate on aluminum, titanium, tungsten, tantalum, titanium nitride, titanium tungsten, tetraethyl orthosilicate (TEOS), silicon nitride, polysilicon and the like, has strong corrosion inhibition on various metals and dielectrics, and has good compatibility and a good cleaning effect.
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions.
Abbreviations referred to in the examples are as follows:
TMAH-tetramethylammonium hydroxide;
al-aluminum; ti-titanium; w-tungsten; TiN-titanium nitride; TEOS-ethyl orthosilicate; SiN-silicon nitride; TiW-titanium tungsten; ta-tantalum.
The EO-PO products in the examples were obtained from Nantong Koilai chemical Co.
Examples 1 to 14
Preparation of cyclodextrin modified alkylene glycol alkyl ether compound
The cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and alkylene glycol alkyl ether compound, and comprises the following steps:
(1) reacting a mixed solution of an alkylene glycol alkyl ether compound, maleic anhydride and a solvent to obtain a substance A; wherein the feeding molar ratio of the alkylene glycol alkyl ether compound to the maleic anhydride is 1.01-1.05: 1. The solvent is preferably an aromatic hydrocarbon solvent, and is more preferably toluene; the temperature of the reaction is preferably 80 ℃ to 100 ℃, for example, 90 ℃; the reaction time is preferably 8 to 12 hours.
(2) Dissolving the substance A obtained in the step (1), cyclodextrin and p-toluenesulfonic acid in a solvent to react to obtain a cyclodextrin modified alkylene glycol alkyl ether compound; wherein the feeding molar ratio of the substance A to the cyclodextrin is 1:1.2-1:1.6, and the mass of the p-toluenesulfonic acid is 0.01-1% of the total mass of the substance A and the cyclodextrin. The solvent is preferably an aromatic hydrocarbon solvent, and is more preferably toluene; the temperature of the reaction is preferably 120 ℃ to 140 ℃, for example, 130 ℃; the reaction time is preferably 32 to 38 hours, for example, 36 hours.
The cyclodextrin can be one or more of alpha-cyclodextrin, beta-cyclodextrin and gamma-cyclodextrin, and beta-cyclodextrin is preferred.
The alkylene glycol alkyl ether compound is preferably one or more of monoalkylene glycol monoalkyl ether, dialkylene glycol monoalkyl ether and trialkylene glycol monoalkyl ether. The monoalkylene glycol monoalkyl ether is preferably one or more of ethylene glycol monobutyl ether, ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; the dialkylene glycol monoalkyl ether is preferably diethylene glycol monobutyl ether and/or diethylene glycol monomethyl ether; the said trialkyl glycol monoalkyl ether is preferably one or more of triethylene glycol monobutyl ether, triethylene glycol monoether, triethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether and tripropylene glycol monomethyl ether.
Preparation of low hydroxylamine water-base cleaning liquid
The raw material components of the low hydroxylamine water-based cleaning solution are as follows: the kinds and contents of the hydroxylamine-based compound, the alcohol amine, the quaternary ammonium base, the chelating agent, the polyquaternary ammonium salt surfactant, the nonionic surfactant, and the cyclodextrin-modified alkylene glycol alkyl ether compound are shown in tables 1 and 2; the water in the low hydroxylamine water-based cleaning solution is deionized water, and the balance is made up by the deionized water.
In the following examples, the preparation method of the low hydroxylamine water-based cleaning solution is to add the solid components in the raw material components in the examples to the liquid components and stir them uniformly.
In the following examples, the specific operation temperature is not limited, and all the operations are carried out at room temperature.
TABLE 1 kinds of raw material components of the low-hydroxylamine aqueous cleaning solution
Figure BDA0002422380640000081
Figure BDA0002422380640000091
TABLE 2 Mass fractions of respective raw material components of the low-hydroxylamine aqueous cleaning solution
Figure BDA0002422380640000092
Figure BDA0002422380640000101
In table 1, the cyclodextrin-modified alkylene glycol alkyl ether compound (a1-a2) was prepared as described above, and the alkylene glycol alkyl ether compound and cyclodextrin involved in the steps (1) and (2) are shown in table 3.
TABLE 3
Numbering Alkylene glycol alkyl ether compound Cyclodextrin
A1 Ethylene glycol monobutyl ether Beta-cyclodextrin
A2 Diethylene glycol monobutyl ether Beta-cyclodextrin
Application examples 1 to 14
Etching rate of a sample to be detected: dummy wafers of a single material, such as aluminum, copper, titanium nitride, tungsten, cobalt, dielectric materials (low-k or high-k), etc., are deposited on a silicon wafer.
Etching experiment: statically dipping a sample to be detected in a low hydroxylamine water-based cleaning solution for 30min at 75 ℃, cleaning by deionized water and drying by nitrogen.
Method for measuring etch rate (A/min): the thickness of the sample before and after etching was measured, respectively, with a metal sample being measured for thickness using a four-point probe apparatus (createst-e of Napson, japan) and a non-metal sample being measured for thickness using an optical film thickness measuring apparatus (filmmetrics F20, usa).
The corrosion effect is classified into four grades: good A-compatibility without undercutting; b-there is very slight undercut; c-there is little undercut; d-undercut is more pronounced and severe.
(2) Measurement of cleaning Effect
Cleaning effect to detect samples: patterned wafers with post plasma etch and post ash residues with pattern features (metal lines, vias via, metal pads pad, trench, etc.).
The cleaning effect experiment method comprises the following steps: statically dipping the sample in a low hydroxylamine water-based cleaning solution for 20min at 75 ℃, then cleaning the sample by deionized water and drying the sample by nitrogen. The cleaning and corrosion effects were observed by electron microscope SEM.
The cleaning effect is divided into four grades: a-no residue was observed; b-very little residue was observed; C-Small residue observed; d-significantly more residue was observed.
The etching rate (A/min), etching effect and cleaning effect of the low hydroxylamine water-based cleaning solutions of examples 1 to 14 are shown in Table 4.
TABLE 4
Figure BDA0002422380640000111
From the application examples (1-14), the low-hydroxylamine water-based cleaning solution disclosed by the invention has lower etching rates on Al, Ti, W, TiN, TEOS, SiN, TiW, Ta, polysilicon and the like, and the corrosion inhibition performance is better; and after the patterned wafer with the through hole characteristic and the patterned wafer with the metal wire characteristic are cleaned by the low hydroxylamine water-based cleaning solution, almost no undercut phenomenon is observed, which shows that the low hydroxylamine water-based cleaning solution has good compatibility to various metals and dielectrics.
In addition, after the patterned wafer with the through hole feature and the patterned wafer with the metal line feature were cleaned with the low hydroxylamine aqueous based cleaning solution of the present invention, almost no residue was observed, indicating that the cleaning effect was good.
Comparative examples 1 to 10
The preparation process is as in examples 1 to 14.
TABLE 5 kinds of raw material components of the low-hydroxylamine aqueous cleaning solutions
Figure BDA0002422380640000121
Figure BDA0002422380640000131
TABLE 6 Mass fractions of respective raw material components of the low-hydroxylamine aqueous-based cleaning solution
Figure BDA0002422380640000132
The low hydroxylamine aqueous cleaning liquids of comparative examples 1 to 10 were subjected to the etching rate (A/min), the etching effect and the cleaning effect in the same manner as in application examples 1 to 14, and the results are shown in Table 7.
TABLE 7
Figure BDA0002422380640000133
Figure BDA0002422380640000141
As can be seen from Table 7, the low hydroxylamine aqueous cleaning solutions of comparative examples 1 to 10 showed significantly higher etching rates for CAl, Ti, W, TiN, TEOS, SiN, TiW, Ta and polysilicon and inferior corrosion inhibition performance as compared with examples 1 to 14.
Also, after the patterned wafers having the via hole features and the patterned wafers having the metal line features were cleaned with the low hydroxylamine aqueous based cleaning solutions of comparative examples 1 to 10, a severe undercut phenomenon occurred with more residue.

Claims (10)

1. The low-hydroxylamine water-based cleaning solution is characterized by being prepared from the following raw materials in parts by mass: 0.1-5% of hydroxylamine compound, 0.5-20% of alcohol amine, 0.1-20% of quaternary ammonium base, 0.01-30% of chelating agent, 0.1-20% of polyquaternary ammonium salt surfactant, 0.1-15% of nonionic surfactant, 0.1-25% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials;
wherein the polyquaternium surfactant is polyquaternium-16;
the nonionic surfactant is one or more of EO-PO polymer L42, EO-PO polymer L43 and EO-PO polymer L44.
2. The low hydroxylamine aqueous cleaning solution of claim 1 wherein,
the mass fraction of the hydroxylamine compound is 0.5-5%, and the mass fraction is the percentage of the mass of the hydroxylamine compound in the total mass of the raw materials;
and/or the mass fraction of the alcohol amine is 1-10%, and the mass fraction is the percentage of the mass of the alcohol amine in the total mass of the raw materials;
and/or the mass fraction of the quaternary ammonium hydroxide is 1-10%, and the mass fraction is the percentage of the mass of the quaternary ammonium hydroxide in the total mass of the raw materials;
and/or the mass fraction of the chelating agent is 1-10%, and the mass fraction is the percentage of the mass of the chelating agent in the total mass of the raw materials;
and/or the mass fraction of the polyquaternium surfactant is 0.5-5%, and the mass fraction is the percentage of the mass of the polyquaternium surfactant in the total mass of the raw materials;
and/or the mass fraction of the nonionic surfactant is 1-5%, and the mass fraction is the percentage of the mass of the nonionic surfactant in the total mass of the raw materials;
and/or the mass fraction of the cyclodextrin modified alkylene glycol alkyl ether compound is 0.5-10%, and the mass fraction is the mass percentage of the cyclodextrin modified alkylene glycol alkyl ether compound in the total mass of the raw materials.
3. The low hydroxylamine aqueous cleaning solution of claim 2 wherein,
the mass fraction of the hydroxylamine compound is 1% -5%, and the mass fraction is the percentage of the hydroxylamine compound in the total mass of the raw materials;
and/or the mass fraction of the alcohol amine is 5-7%, and the mass fraction is the percentage of the mass of the alcohol amine in the total mass of the raw materials;
and/or the mass fraction of the quaternary ammonium hydroxide is 5-10%, and the mass fraction is the percentage of the mass of the quaternary ammonium hydroxide in the total mass of the raw materials;
and/or the mass fraction of the chelating agent is 5-10%, and the mass fraction is the percentage of the mass of the chelating agent in the total mass of the raw materials;
and/or the mass fraction of the polyquaternium surfactant is 1-2%, and the mass fraction is the percentage of the total mass of the raw materials in the mass of the polyquaternium surfactant;
and/or the mass fraction of the nonionic surfactant is 1-2%, and the mass fraction is the percentage of the mass of the nonionic surfactant in the total mass of the raw materials;
and/or the mass fraction of the cyclodextrin modified alkylene glycol alkyl ether compound is 1-5%, and the mass fraction is the percentage of the mass of the cyclodextrin modified alkylene glycol alkyl ether compound in the total mass of the raw materials.
4. The low hydroxylamine aqueous cleaning solution of claim 1 wherein,
the hydroxylamine compound is one or more of hydroxylamine, N-methylhydroxylamine, N-ethylhydroxylamine, N-diethylhydroxylamine, hydroxylamine sulfate, hydroxylamine nitrate, hydroxylamine phosphate, hydroxylamine chloride, hydroxylamine oxalate and hydroxylamine citrate;
and/or the alcohol amine is one or more of monoethanolamine, diethanolamine, triethanolamine, 2-aminoethanol, 1-amino-2-propanol, 1-amino-3-propanol, 2- (2-aminoethoxy) ethanol, 2- (2-aminoethylamino) ethylamine, trimethanolamine, diglycolamine, dilactolamine, n-propanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine and diethanolisopropanolamine;
and/or the quaternary ammonium base is tetramethylammonium hydroxide, choline, trimethyl-3-hydroxypropylammonium hydroxide, trimethyl-3-hydroxybutylammonium hydroxide, trimethyl-4-hydroxybutylammonium hydroxide, triethyl-2-hydroxyethylammonium hydroxide, tripropyl-2-hydroxyethylammonium hydroxide, tributyl-2-hydroxyethylammonium hydroxide, dimethylethyl-2-hydroxyethylammonium hydroxide, dimethyldi- (2-hydroxyethyl) ammonium hydroxide, monomethyltriethanolamine hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, tetraethanolammonium hydroxide, monomethyltriethylammonium hydroxide, monomethyltripropylammonium hydroxide, monomethyltributylammonium hydroxide, tetramethylammonium hydroxide, or mixtures thereof, One or more of monoethyltrimethylammonium hydroxide, monoethyltributylammonium hydroxide, dimethyldiethylammonium hydroxide, dimethyldibutylammonium hydroxide and benzyltrimethylammonium hydroxide;
and/or the chelating agent is one or more of catechol, pyrogallol, gallic acid, alkyl gallate, alkyl catechol, malonic acid, maleic acid and tartaric acid;
and/or, the nonionic surfactant is EO-PO polymer L42;
and/or the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, and comprises the following steps:
(1) reacting a mixed solution of an alkylene glycol alkyl ether compound, maleic anhydride and a solvent to obtain a substance A;
(2) reacting the substance A obtained in the step (1), cyclodextrin and p-toluenesulfonic acid in a solvent to obtain the compound A;
and/or the water is one or more of deionized water, pure water and ultrapure water.
5. The low hydroxylamine aqueous cleaning solution of claim 4 wherein,
when the chelating agent is alkyl gallate, the alkyl gallate is methyl gallate and/or propyl gallate;
and/or, when the chelating agent is alkyl catechol, the alkyl catechol is one or more of methyl catechol, ethyl catechol and tert-butyl catechol;
and/or when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, the cyclodextrin is one or more of alpha-cyclodextrin, beta-cyclodextrin and gamma-cyclodextrin;
and/or when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, the alkylene glycol alkyl ether compound is one or more of monoalkylene glycol monoalkyl ether, dialkylene glycol monoalkyl ether and trialkylene glycol monoalkyl ether;
the monoalkylene glycol monoalkyl ether is preferably one or more of ethylene glycol monobutyl ether, ethylene glycol monomethyl ether and ethylene glycol monoethyl ether;
the dialkylene glycol monoalkyl ether is preferably diethylene glycol monobutyl ether and/or diethylene glycol monomethyl ether;
the preferable trialkyl glycol monoalkyl ether is one or more of triethylene glycol monobutyl ether, triethylene glycol monoether, triethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether and tripropylene glycol monomethyl ether;
and/or when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, in the step (1), the feeding molar ratio of the alkylene glycol alkyl ether compound to the maleic anhydride is 1.01-1.05: 1;
and/or, when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, in the step (1), the solvent is an aromatic hydrocarbon solvent;
and/or when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, in the step (1), the reaction temperature is 80-100 ℃;
and/or, when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, in the step (1), the reaction time is 8-12 hours;
and/or when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, in the step (2), the feeding molar ratio of the substance A to the cyclodextrin is 1:1.2-1: 1.6;
and/or when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, in the step (2), the mass of the p-toluenesulfonic acid is 0.01-1% of the total mass of the substance A and the cyclodextrin;
and/or, when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, in the step (2), the solvent is an aromatic hydrocarbon solvent;
and/or when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, in the step (2), the reaction temperature is 120-140 ℃;
and/or, when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared by reacting cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, in the step (2), the reaction time is 32-38 hours.
6. The low hydroxylamine aqueous cleaning solution of claim 4 wherein,
the hydroxylamine compound is hydroxylamine;
and/or the alcohol amine is one or more of monoethanolamine, triethanolamine, diglycolamine and isopropanolamine;
and/or, the quaternary ammonium hydroxide is tetramethylammonium hydroxide and/or choline;
and/or the chelating agent is one or more of gallic acid, malonic acid and tartaric acid;
and/or, when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared from cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, the cyclodextrin is beta-cyclodextrin;
and/or when the cyclodextrin modified alkylene glycol alkyl ether compound is prepared from cyclodextrin, maleic anhydride and an alkylene glycol alkyl ether compound, the alkylene glycol alkyl ether compound is ethylene glycol monobutyl ether and/or diethylene glycol monobutyl ether;
and/or the water is deionized water.
7. The aqueous cleaning solution of hydroxylamine of claim 1 to 6, wherein the aqueous cleaning solution of hydroxylamine is one of the following solutions,
scheme 1:
the low-hydroxylamine water-based cleaning solution is prepared from the following raw materials in parts by mass: 0.5-5% of hydroxylamine compound, 1-10% of alcohol amine, 1-10% of quaternary ammonium base, 1-10% of chelating agent, 0.5-5% of polyquaternary ammonium salt surfactant, 1-5% of nonionic surfactant, 0.5-10% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials;
scheme 2:
the low-hydroxylamine water-based cleaning solution is prepared from the following raw materials in parts by mass: 1-5% of hydroxylamine compound, 5-7% of alcohol amine, 5-10% of quaternary ammonium base, 5-10% of chelating agent, 1-2% of polyquaternary ammonium salt surfactant, 1-2% of nonionic surfactant, 1-5% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials;
scheme 3:
the low-hydroxylamine water-based cleaning solution is prepared from the following raw materials in parts by mass: 0.1-5% of hydroxylamine compound, 0.5-20% of alcohol amine, 0.1-20% of quaternary ammonium base, 0.01-30% of chelating agent, 0.1-20% of polyquaternary ammonium salt surfactant, 0.1-15% of nonionic surfactant, 0.1-25% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials;
scheme 4:
the low-hydroxylamine water-based cleaning solution is prepared from the following raw materials in parts by mass: 0.5-5% of hydroxylamine compound, 1-10% of alcohol amine, 1-10% of quaternary ammonium base, 1-10% of chelating agent, 0.5-5% of polyquaternary ammonium salt surfactant, 1-5% of nonionic surfactant, 0.5-10% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials;
scheme 5:
the low-hydroxylamine water-based cleaning solution is prepared from the following raw materials in parts by mass: 1-5% of hydroxylamine compound, 5-7% of alcohol amine, 5-10% of quaternary ammonium base, 5-10% of chelating agent, 1-2% of polyquaternary ammonium salt surfactant, 1-2% of nonionic surfactant, 1-5% of cyclodextrin modified alkylene glycol alkyl ether compound and the balance of water, wherein the mass fraction is the percentage of the mass of each component in the total mass of the raw materials.
8. A method of preparing a low hydroxylamine aqueous based cleaning solution as claimed in any one of claims 1 to 7, comprising the steps of: and mixing the raw materials to obtain the low hydroxylamine water-based cleaning solution.
9. The method for producing a low hydroxylamine aqueous based cleaning solution as claimed in claim 8,
the mixing is to add the solid component in the raw material components into the liquid component and stir the mixture evenly;
and/or the temperature of the mixing is room temperature.
10. Use of a low hydroxylamine aqueous based cleaning solution as defined in any one of claims 1 to 7 for cleaning a semiconductor device after plasma etching;
wherein, the substrate of plasma etching is preferably an aluminum interconnection substrate;
the cleaning temperature is preferably 60-75 ℃;
the cleaning time is preferably 5min-30 min.
CN202010209649.XA 2020-03-23 2020-03-23 Low-hydroxylamine water-based cleaning solution, and preparation method and application thereof Pending CN113430069A (en)

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