Compositions of Trihaloalkyltin and Related Methods

Abstract

The present disclosure includes a method of obtaining a trihaloalkyltin, obtaining a solvent, and contacting the trihaloalkyltin with the solvent, thereby forming a trihaloalkyltin adduct. The formula: RSnX 3 ·(solv) n [wherein, R is a substituted C 1 ~C 5 alkyl, an unsubstituted C 1 ~C 5 alkyl, a substituted C 1 ~C 5 alkenyl, or an unsubstituted C 1 ~C 5 alkenyl, X is Cl, Br or I, solv is a solvent, and n is at least 1] also describes a composition comprising a trihaloalkyltin adduct.

Description

Technical Field

[0001] The present disclosure relates to the field of compositions of trihaloalkyltin and related methods.

[0002] Priority The present disclosure claims priority to U.S. Provisional Patent No. 63 / 348,859, having a filing date of June 3, 2022, and U.S. Provisional Patent No. 63 / 400,269, having a filing date of August 23, 2022. Both priority documents are incorporated herein by reference.

Background Art

[0003] Films can be used for applications during the manufacture of microelectronic devices. Some films can be made using chemical vapor deposition or atomic layer deposition.

Summary of the Invention

[0004] The present disclosure relates to an adduct of trihaloalkyltin comprising a solvent-based adduct of trihaloalkyltin for the production of high-purity (e.g., greater than 95% purity) extreme ultraviolet atomic layer deposition precursors. In some embodiments, the purity is greater than 99.8%. The present disclosure also relates to the synthesis of compounds such as tris(dimethylamido)tin alkyl compounds with little or no dialkyl impurities.

[0005] The present disclosure addresses the problem of producing high-purity tris(dimethylamido)alkyltin compounds with little or no dialkyl impurities. Further, the present disclosure has fewer steps for synthesizing the compound and lower costs for manufacturing the compound.

[0006] The present disclosure describes a direct route for making RSn(NMe 2 ) 3 In some embodiments, as further described herein, R can be isopropenyl, isopropyl, or ethyl. By a solvent-based approach, the present disclosure provides R 2 Sn(NMe2 ) 2 To reduce the impurity profile, the need to make an adduct of RSnCl 3 compound with HNMe 2 can be avoided.

[0007] The synthesis depends on the R group and the solvent / solution. The choice of solvent / solution (e.g., tetrahydrofuran (THF), dimethoxyethane (DME), or hexane) is a factor that provides a sufficient yield and purity of the final product.

[0008] The present disclosure effectively provides synthons for producing the desired tris(dimethylamide)alkyltin product in high purity using a coordinating solvent, the isolable alkyltin trichloride adduct alkylSnCl 3 (solv) 1-2 is formed. The method of the present disclosure requires fewer reagents and steps than current processes for producing alkyltin trichloride adducts and thus provides a faster and less expensive process.

[0009] In some embodiments, the techniques described herein relate to a method comprising obtaining a trihaloalkyltin, obtaining a solvent, solution, or any combination thereof, and contacting the trihaloalkyltin with the solvent, solution, or any combination thereof to form a trihaloalkyltin adduct.

[0010] In some embodiments, the techniques described herein relate to a method that does not include forming a trihaloalkyltin-amine adduct.

[0011] In some embodiments, the techniques described herein relate to a method in which the trihaloalkyltin-amine adduct is a trihaloalkyltin-(HNMe 2 ) adduct.

[0012] In some embodiments, the trihaloalkyltin described herein has the formula: RSnX3 [In the formula, R is a substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, and X is Cl, Br, or I], and relates to a method of a compound.

[0013] In some embodiments, the techniques described herein relate to methods where R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 CF 2 HCH 2 CFH 2 CH 2 CFH 2 , or CFH

[0014] In some embodiments, the techniques described herein relate to methods where R is alkoxy.

[0015] In some embodiments, the techniques described herein relate to methods where R is vinyl, allyl, propynyl, propenyl, or any isomers thereof.

[0016] In some embodiments, the techniques described herein relate to methods where the solvent comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

[0017] In some embodiments, the techniques described herein relate to methods in which the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0018] In some embodiments, the techniques described herein relate to methods in which the trihaloalkyltin adduct is a compound of the formula: RSnX 3 ·(solv) n [wherein R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, X is Cl, Br or I, solv is a solvent, and n is at least 1].

[0019] In some embodiments, the techniques described herein relate to methods that include obtaining a trihaloalkyltin adduct, obtaining a lithium dialkylamide, and contacting the trihaloalkyltin adduct with the lithium dialkylamide to form a tris(dialkylamide)alkyltin product.

[0020] In some embodiments, the techniques described herein relate to methods that do not include forming a trihaloalkyltin-amine adduct.

[0021] In some embodiments, the techniques described herein relate to methods in which the trihaloalkyltin-amine adduct is a trihaloalkyltin-(HNMe 2 ) adduct.

[0022] In some embodiments, the techniques described herein relate to methods in which the trihaloalkyltin adduct is a compound of the formula: RSnX 3 ·(solv) n [wherein R is a substituted C 1 -C 5 alkyl, an unsubstituted C 1 -C 5 alkyl, a substituted C 1 -C 5 alkenyl, or an unsubstituted C 1 -C 5 alkenyl, X is Cl, Br or I, solv is a solvent, and n is at least 1].

[0023] In some embodiments, the techniques described herein relate to methods in which R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 , CF 2 HCH 2 , CFH 2 CH 2 , or CFH 2 . In some embodiments, the techniques described herein relate to methods in which R is an alkoxy.

[0024] In some embodiments, the techniques described herein relate to methods in which R is vinyl, allyl, propynyl, propenyl, or any isomers thereof.

[0025] In some embodiments, the techniques described herein relate to a method in which the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, hexane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0026] In some embodiments, the techniques described herein relate to a method in which the lithium dialkylamide is a compound of the formula: LiN(R 1 ) 2 [wherein R 1 is C 1 to C 3 alkyl].

[0027] In some embodiments, the techniques described herein relate to a method in which the tris(dialkylamide)alkyltin product is of the formula: TIFF2025518177000002.tif48170[wherein R is substituted C 1 to C 5 alkyl, unsubstituted C 1 to C 5 alkyl, substituted C 1 to C 5 alkenyl, or unsubstituted C 1 to C 5 alkenyl, and each R1 is independently C 1 to C 3 alkyl].

[0028] In some embodiments, the techniques described herein relate to a method comprising obtaining a trihaloalkyltin, obtaining a solvent, a solution, or any combination thereof, contacting the trihaloalkyltin with the solvent, the solution, or any combination thereof to form a trihaloalkyltin adduct, obtaining a lithium dialkylamide, and contacting the trihaloalkyltin adduct with the lithium dialkylamide to form a tris(dialkylamide)alkyltin product.

[0029] In some embodiments, the techniques described herein relate to a method that does not include forming a trihaloalkyltin-amine adduct.

[0030] In some embodiments, the techniques described herein relate to a method in which the trihaloalkyltin-amine adduct is a trihaloalkyltin-(HNMe 2 ) adduct.

[0031] In some embodiments, the techniques described herein relate to a method in which the trihaloalkyltin is a compound of the formula: RSnX 3 [wherein R is a substituted C 1 -C 5 alkyl, an unsubstituted C 1 -C 5 alkyl, a substituted C 1 -C 5 alkenyl, or an unsubstituted C 1 -C 5 alkenyl, and X is Cl, Br, or I].

[0032] In some embodiments, the techniques described herein relate to a method in which R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 , CF 2 HCH 2 , CFH 2 CH 2 , or CFH2 Relates to a method. In some embodiments, the techniques described herein relate to a method in which R is an alkoxy group.

[0033] In some embodiments, the techniques described herein relate to a method in which R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0034] In some embodiments, the techniques described herein relate to a method in which the solvent comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

[0035] In some embodiments, the techniques described herein relate to a method in which the solution comprises at least one of hexane, pentane, toluene, or any combination thereof.

[0036] In some embodiments, the techniques described herein relate to a method in which the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomer thereof, or any combination thereof.

[0037] In some embodiments, the techniques described herein relate to a trihaloalkyltin adduct having the formula: RSnX 3 ·(solv) n [wherein, R is a substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, X is Cl, Br or I, solv is a solvent, and n is at least 1] of the compound.

[0038] In some embodiments, the techniques described herein are such that the lithium dialkylamide has the formula: LiN(R 1 ) 2 [wherein R 1 is C 1 ~C 3 alkyl-containing] of the compound.

[0039] In some embodiments, the techniques described herein are such that the tris(dialkylamide)alkyltin product has the formula: TIFF2025518177000003.tif48170[wherein R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, and each R 1 is independently C 1 ~C 3 alkyl] of the compound.

[0040] In some embodiments, the techniques described herein are such that the formula: RSnX 3 ·(solv) n [wherein R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5Relates to a composition comprising a trihalogenated alkyltin adduct of the formula: [[wherein R is alkenyl, X is Cl, Br or I, solv is a solvent, and n is at least 1]].

[0041] In some embodiments, the techniques described herein relate to a composition wherein the solvent comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), hexane, or any combination thereof.

[0042] In some embodiments, the techniques described herein relate to a composition wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, hexane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0043] In some embodiments, the techniques described herein relate to a compound of the formula: TIFF2025518177000004.tif48170[wherein R is substituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, and each R1 is independently C 1 ~C 3 alkyl].

[0044] In some embodiments, the techniques described herein relate to compositions wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 、CF 2 HCH 2 、CFH 2 CH 2 、or CFH 2 . In some embodiments, the techniques described herein relate to methods wherein R is alkoxy.

[0045] In some embodiments, the techniques described herein relate to compositions wherein R is vinyl, allyl, propynyl, propenyl, or any isomers thereof.

[0046] In some embodiments, the techniques described herein relate to compositions comprising the reaction product of a trihaloalkyltin adduct and a lithium dialkylamide, the reaction product having the formula: TIFF2025518177000005.tif48170[wherein R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, and each R 1 is independently C 1 ~C 5 alkyl].

[0047] In some embodiments, the techniques described herein relate to compositions wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 、CF 2 HCH 2 、CFH 2 CH2 or CFH 2 relates to a composition that is. In some embodiments, the techniques described herein relate to a method in which R is an alkoxy group.

[0048] In some embodiments, the techniques described herein relate to a composition in which R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0049] In some embodiments, the techniques described herein relate to the formula: RSnX 3 [wherein R is a substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, and X is Cl, Br or I] relates to a composition comprising an atomic layer deposition precursor comprising a trihalogenated alkyltin adduct.

[0050] In some embodiments, the techniques described herein relate to a composition in which R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 、CF 2 HCH 2 、CFH 2 CH 2 、or CFH 2 is.

[0051] In some embodiments, the techniques described herein relate to a composition in which R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0052] In some embodiments, the techniques described herein relate to the formula: RSnX 3 [wherein R is a substituted C 1 ~C 5 alkyl, unsubstituted C1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 relates to a composition comprising a chemical vapor deposition precursor comprising a trihalogenated alkyltin adduct wherein R is alkenyl and X is Cl, Br or I.

[0053] In some embodiments, the techniques described herein relate to compositions wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 , CF 2 HCH 2 , CFH 2 CH 2 , or CFH 2 and relates to a composition.

[0054] In some embodiments, the techniques described herein relate to compositions wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0055] In some embodiments, the techniques described herein relate to a formula: TIFF2025518177000006.tif42170

[0056] [wherein,

[0057] R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, and

[0058] R 2 is independently substituted C 1 ~C 4 alkyl or unsubstituted C 1~C 4 is alkyl, substituted C 1 ~C 4 The alkyl contains a fluorine-containing substituent] relates to a compound containing the compound of.

[0059] In some embodiments, the techniques described herein are for R 2 of C 1 ~C 4 relate to compositions wherein the alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, or tert-butyl.

[0060] In some embodiments, the techniques described herein are for compositions wherein the fluorine-containing substituent is -CH 2 CF 3 , -CH(CF 3 ) 2 , or -(CH a ) n (CH b F c ) m wherein a = 0 to 3; b = 0 to 2; c = 1 to 3; n = 0 to 3; m = 1 to 4.

[0061] In some embodiments, the techniques described herein are for compositions wherein -(CH a ) n (CH b F c ) m is -CH 2 F, -CH 2 CH 2 F, -CF 3 , or -CF 2 CF 3 .

[0062] In some embodiments, the techniques described herein are for compositions wherein R 2 is saturated alkyl or unsaturated alkyl.

[0063] In some embodiments, the techniques described herein are for compositions wherein OR 2 is -OCH 2C≡CH or -OCH=CH 2 relates to a composition that is

[0064] In some embodiments, the technology described herein is of the formula: RSn(OR 2 ) 3 [wherein, R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, and R 2 are independently substituted C 1 ~C 4 alkyl or unsubstituted C 1 ~C 4 alkyl, and substituted C 1 ~C 4 alkyl contains a fluorine-containing substituent] and relates to a composition containing a compound of

[0065] In some embodiments, the technology described herein is such that the C 2 of R 1 ~C 4 alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, or tert-butyl, and relates to a composition

[0066] In some embodiments, the technology described herein is such that the fluorine-containing substituent is -CH 2 CF 3 , -CH(CF 3 ) 2 , or -(CH a ) n (CH b F c ) m wherein a = 0 to 3; b = 0 to 2; c = 1 to 3; n = 0 to 3; m = 1 to 4, and relates to a composition

[0067] In some embodiments, the technology described herein is such that -(CH a ) n (CHb F c ) m is -CH 2 F, -CH 2 CH 2 F, -CF 3 , or -CF 2 CF 3 relates to a composition that is

[0068] In some embodiments, the techniques described herein relate to a composition in which R 2 is a saturated alkyl or an unsaturated alkyl.

[0069] In some embodiments, the techniques described herein relate to a composition in which OR 2 is -OCH 2 C≡CH or -OCH=CH 2 is.

[0070] Some embodiments of the present disclosure are described herein by way of example only with reference to the accompanying drawings. Referring particularly to the drawings in detail here, it is emphasized that the embodiments shown are by way of example and for purposes of illustrative explanation of the embodiments of the present disclosure. In this regard, the description made with the use of the drawings makes it clear to those skilled in the art how the embodiments of the present disclosure can be implemented.

Brief Description of the Drawings

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DETAILED DESCRIPTION OF THE INVENTION

[0072] Among these disclosed advantages and improvements, other objects and advantages of the present disclosure will become apparent from the following description in conjunction with the accompanying drawings. Specific embodiments of the present disclosure are disclosed herein. However, it should be understood that the disclosed embodiments are merely exemplary of the present disclosure, which can be embodied in various forms. Further, each of the examples given with respect to the various embodiments of the present disclosure is intended to be illustrative and not limiting.

[0073] All prior patents and publications referred to in this specification are incorporated by reference in their entirety.

[0074] Throughout the specification and claims, the following terms take the meanings explicitly associated with them in this specification, unless the context clearly indicates otherwise. The phrases "in one embodiment," "in embodiments," and "in some embodiments" as used herein do not necessarily refer to the same embodiment, but may. Further, the phrases "in another embodiment" and "in some other embodiments" as used herein do not necessarily refer to different embodiments, but may. All embodiments of the present disclosure are intended to be combinable without departing from the scope or spirit of the present disclosure.

[0075] As used herein, the term "based on" is not exclusive and allows for being based on additional factors not recited, unless the context clearly dictates otherwise. Further, throughout this specification, the meanings of "a," "an," and "the" include plural references. The meaning of "in" includes "in" and "on."

[0076] FIG. 1 shows a non-limiting embodiment of method 100 of the present disclosure described herein. Method 100 includes one or more of the following steps. The first step 110 includes obtaining an alkyl tin trihalide. The second step 120 includes obtaining a solvent, a solution, or any combination thereof. The third step 130 includes contacting the alkyl tin trihalide with a solvent, a solution, or any combination thereof, thereby forming an alkyl tin trihalide adduct. The fourth step 140 includes obtaining the alkyl tin trihalide adduct. The fifth step 150 includes obtaining a lithium dialkylamide. The sixth step 160 includes contacting the alkyl tin trihalide adduct with the lithium dialkylamide, thereby forming a tris(dialkylamide)alkyl tin product.

[0077] Method 100 can include any combination of steps. For example, in some embodiments, method 100 can include a first step 110, a second step 120, and a third step 130. In some embodiments, method 100 can include a fourth step 140, a fifth step 150, and a sixth step 160. In some embodiments, method 100 can include the first step 110, the second step 120, and the third step 130, the fourth step 140, the fifth step 150, and the sixth step 160.

[0078] In some embodiments, method 100 does not include forming a trihaloalkyltin - amine adduct. In some embodiments, the trihaloalkyltin - amine adduct is a trihaloalkyltin-(HNMe 2 ) adduct. For example, in some embodiments, the trihaloalkyltin-(HNMe 2 ) adduct has two amines-(HNMe 2 ) 2 .

[0079] The present disclosure relates to an adduct of a trihaloalkyltin comprising a solvent - based adduct of a trihaloalkyltin for the manufacture of a high - purity (e.g., greater than 95% purity) extreme ultraviolet atomic layer deposition precursor. In some embodiments, the purity is greater than 95%, 95.5%, 96%, 96.5%, 97%, 97.5%, 98%, 98.5%, 99%, 99.1%, 99.2%, 99.3%, 99.4%, 99.5%, 99.6%, 99.7%, 99.8%, 99.9%, 99.91%, 99.92%, 99.93%, 99.94%, 99.95%, 99.96%, 99.97%, 99.98%, or 99.99%.

[0080] In some embodiments, the trihaloalkyltin (see, e.g., the first step 110) is a compound of the formula RSnX 3 . In some embodiments, R is a substituted C 1 ~C 5 alkyl, an unsubstituted C 1~C 5 Alkyl, substituted C 1 ~C 5 Alkenyl, unsubstituted C 1 ~C 5 Alkenyl, substituted C 1 ~C 5 Alkynyl, or unsubstituted C 1 ~C 5 is alkynyl. In some embodiments, X is Cl, Br, or I.

[0081] In some embodiments, the solvent (see, e.g., the second step 120) comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

[0082] In some embodiments, the solution (see, e.g., the second step 120) comprises at least one of hexane, pentane, toluene, or any combination thereof.

[0083] In some embodiments, the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0084] In some embodiments, the trihaloalkyltin adduct (see, e.g., the third step 130 and / or the fourth step 140) has the formula RSnX 3 ·(solv) nis a compound. In some embodiments, R is a substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl. X is Cl, Br, or I. In some embodiments, solv is a solvent. In some embodiments, n is at least 1.

[0085] In some embodiments, lithium dialkylamide (see, e.g., step 5 150) is a compound of the formula LiN(R 1 ) 2 . In some embodiments, R 1 is C 1 ~C 3 alkyl.

[0086] In some embodiments, the present disclosure includes a composition comprising a tris(dialkylamide)alkyltin product (see, e.g., step 6 160).

[0087] In some embodiments, the present disclosure includes a composition comprising a reaction product of a trihalogenated alkyltin adduct and a lithium dialkylamide.

[0088] In some embodiments, the tris(dialkylamide)alkyltin product (see, e.g., step 6 160) is a compound of the formula: TIFF2025518177000007.tif48170.

[0089] In some embodiments, R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 , CF 2 HCH 2 , CFH 2 CH2 , CFH 2 or is an alkoxy group.

[0090] In some embodiments, R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0091] In some embodiments, R is a substituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl. In some embodiments, each R 1 is independently C 1 ~C 3 alkyl.

[0092] In some embodiments, each R and each R 1 can be independently selected from straight-chain or branched-chain alkyl groups including methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, or sec-pentyl groups. In one particular embodiment, each R and each R 1 is independently selected from C 1 ~C 3 alkyl groups such as methyl, ethyl, or propyl groups. In some embodiments, R or R 1 can be a substituted or unsubstituted straight-chain or branched-chain alkyl group selected from C 1 ~C 5 alkyl groups. For example, R or R 1 can be a straight-chain or branched-chain alkyl group including methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, or sec-pentyl groups. Further, R or R 1 can be a cyclic C 1 ~C 5 group such as a cyclopropyl group. Also, R or R 1 can be an unsaturated C 1 ~C5 may also be a radical. R or R 1 Either of the radicals may be further substituted with one or more halogen groups or ether groups, etc. For example, R or R 1 is a fluorinated alkyl group having the formula -(CH a ) n (CH b F c ) m [wherein, a = 0 to 3; b = 0 to 2; c = 1 to 3; n = 0 to 3; m = 1 to 4], and may include monofluorinated C 2 F or -CH 2 CH 2 F groups such as alkyl groups, and perfluorinated C 1 ~C 5 alkyl groups, and -CF 3 or -CF 2 CF 3 groups such as perfluorinated C 1 ~C 5 groups. Alternatively, R or R 1 may be an alkyl ether group, and the alkyl portion is a C 1 ~C 5 alkyl group. In one specific embodiment, each R and each R 1 is methyl, ethyl, or isopropyl.

[0093] In some embodiments, R or R 1 may be alkyl, alkenyl, alkynyl, alkoxide, carboxylate, ether, nitrile, or imide.

[0094] In some embodiments, R or R 1 is C 1 ~C 5 alkyl (methyl, ethyl, n-propyl, isopropyl, cyclopropyl, sec-butyl, n-butyl, tert-butyl, isoamyl, cyclopentadienyl, vinyl, ethynyl, propynyl, isopropenyl or acetyl).

[0095] In some embodiments, R or R 1is C containing a substituted phenyl or substituted cyclopentadienyl (e.g., indenyl). 6 ~C n may be phenyl.

[0096] In some embodiments, R or R 1 is CF 3 , -CF 2 H, -CFH 2 , CF 3 CH 2 , CF 2 HCH 2 , CFH 2 CH 2 , ICH 2 CH 2 (iodoethane), CH 3 OCH 2 , CH 3 CH 2 OCH 2 , CH 3 CH- 2 OCH 2 CH 2 , CH 3 OCH 2 CH 2 , or a functionalized alkyl containing -C≡N may be used.

[0097] In some embodiments, R or R 1 is CF 3 CO 2 (trifluoroacetate) or CH 3 CO 2 (acetate) may be a carboxylate containing.

[0098] In some embodiments, R or R 1 is an alkoxide (CX n H 3-n CX m H 2-m O-, where X = F, Cl, Br, I and n, m = 0 to 3). For example, R or R 1 is CF 3 CH 2 O- (trifluoroethoxide), CH 3 O- (methoxide), CH3 CH 2 O-(ethoxide), (CH 3 ) 2 CHO-(isopropoxide), (CH 3 ) 3 CO-(tert-butoxide), or HC≡CO-(propargyl alkoxide) may also be used.

[0099] In some embodiments, R or R 1 may be any combination of the compounds described in this disclosure (e.g., fluoroether or fluoroalkoxide).

[0100] Some embodiments relate to a composition. In some embodiments, the composition comprises an atomic layer deposition precursor comprising a trihalogenated alkyltin of the formula: RSnX 3 .

[0101] In some embodiments, R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl. In some embodiments, X is Cl, Br, or I.

[0102] In some embodiments, R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 , CF 2 HCH 2 , CFH 2 CH 2 , or CFH 2 .

[0103] In some embodiments, R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0104] Some embodiments relate to a composition. In some embodiments, the composition comprises a chemical vapor deposition precursor comprising a trihalogenated alkyl tin of the formula: RSnX 3 wherein the chemical vapor deposition precursor comprises a trihalogenated alkyl tin of the formula: RSnX

[0105] In some embodiments, R is a substituted C 1 ~C 5 alkyl, an unsubstituted C 1 ~C 5 alkyl, a substituted C 1 ~C 5 alkenyl, or an unsubstituted C 1 ~C 5 alkenyl. In some embodiments, X is Cl, Br, or I.

[0106] In some embodiments, R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 、CF 2 HCH 2 、CFH 2 CH 2 、or CFH 2 。

[0107] In some embodiments, R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0108] Some embodiments relate to a composition comprising a compound of the formula: TIFF2025518177000008.tif42170.

[0109] In some embodiments, R is a substituted C 1 ~C 5 alkyl, an unsubstituted C 1 ~C 5 alkyl, a substituted C 1 ~C 5 alkenyl, or an unsubstituted C 1 ~C 5 alkenyl.

[0110] In some embodiments, R 2 is, independently, substituted C 1 ~C 4 alkyl or unsubstituted C 1 ~C 4 alkyl. In some embodiments, the substituted C 1 ~C 4 alkyl contains a fluorine-containing substituent.

[0111] In some embodiments, the C 2 of R 1 ~C 4 alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, or tert-butyl.

[0112] In some embodiments, the fluorine-containing substituent is -CH 2 CF 3 , -CH(CF 3 ) 2 , or -(CH a ) n (CH b F c ) m wherein: a = 0 to 3; b = 0 to 2; c = 1 to 3; n = 0 to 3; m = 1 to 4.

[0113] In some embodiments, -(CH a ) n (CH b F c ) m is -CH 2 F, -CH 2 CH 2 F, -CF 3 , or -CF 2 CF 3 .

[0114] In some embodiments, R 2 is saturated alkyl or unsaturated alkyl.

[0115] In some embodiments, OR 2 is -OCH2 C≡CH or -OCH=CH 2 is.

[0116] Some embodiments relate to a composition comprising a compound of the formula: RSn(OR 2 ) 3 .

[0117] In some embodiments, R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl.

[0118] In some embodiments, R 2 is independently substituted C 1 ~C 4 alkyl or unsubstituted C 1 ~C 4 alkyl. In some embodiments, substituted C 1 ~C 4 alkyl contains a fluorine-containing substituent.

[0119] In some embodiments, the C 2 of R 1 ~C 4 alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, or tert-butyl.

[0120] In some embodiments, the fluorine-containing substituent is -CH 2 CF 3 , -CH(CF 3 ) 2 , or -(CH a ) n (CH b F c ) m , where a = 0 to 3; b = 0 to 2; c = 1 to 3; n = 0 to 3; m = 1 to 4.

[0121] In some embodiments, -(CH a ) n (CH b F c ) m is -CH 2 F, -CH 2 CH 2 F, -CF 3 , or -CF 2 CF 3 .

[0122] In some embodiments, R 2 is a saturated alkyl or an unsaturated alkyl.

[0123] In some embodiments, OR 2 is -OCH 2 C≡CH or -OCH=CH 2 .

Example

[0124] Example 1: Synthesis of EtSnCl 3 (THF) 2 In a glove box filled with nitrogen, EtSnCl

[0125] (0.500 g, 1.96 mmol) was placed in a 40 mL vial and diluted with hexane (2 mL). When tetrahydrofuran (0.71 g, 9.84 mmol) was added dropwise to the EtSnCl 3 solution, a white precipitate immediately formed. After the addition of THF was complete, the vial was placed in a freezer at -35 °C for 1 hour, the mother liquor was removed with a pipette, and the remaining white solid was warmed to room temperature and dried under reduced pressure. Upon heating, the product melted to form a colorless liquid. Mass: 3.12 g, yield 99.7%. 3 H-NMR (400 MHz, CDCl 1 , 298 K): 1.32 (t, 3H); 1.74 (t, 8H); 2.13 (q, 2H); 3.67 (t, 8H) ppm; 3 C{ 13 H}-NMR (100 MHz, CDCl 1 , 298 K): 3, 298 K): 9.46; 25.07; 29.20; 68.32 ppm; 119 Sn{ 1 H}-NMR (149 MHz, CDCl 3 , 298 K): -150.98 ppm.

[0126] Figure 2 shows the 3 H-NMR of EtSnCl 3 (THF) 2 recorded in 1 CDCl

[0127] Example 2: Synthesis of EtSnCl 3 (DME)

[0128] In a nitrogen-filled glove box, EtSnCl 3 (0.500 g, 1.96 mmol) was placed in a 40 mL vial and diluted with hexane (2 mL). Dimethoxyethane (1.13 g, 12.5 mmol) was added dropwise to the EtSnCl 3 solution, and a white precipitate immediately formed. After the addition of DME was complete, the vial was placed in a -35 °C freezer for 1 hour. The mother liquor was removed with a pipette, and the remaining white solid was warmed to room temperature and dried under reduced pressure. Mass: 2.70 g, yield 98.8%). M.P.: 61.9 °C (by DSC). X-ray quality crystals were grown by cooling a saturated DME solution of EtSnCl 3 (DME) at -35 °C. 1 H-NMR (400 MHz, CDCl 3, 298 K): 1.46 (t, 3H); 2.28 (q, 2H); 3.39 (s, 6H); 3.56 (s, 4H) ppm; 13 C{ 1 H}-NMR (100 MHz, CDCl 3, 298 K): 9.54; 28.22; 59.26; 71.44 ppm; 119 Sn{ 1 H}-NMR (149 MHz, CDCl 3, 298 K): -49.63 ppm.

[0129] Figure 3 shows the three-dimensional solid-state structure of EtSnCl3(DME) determined by X-ray crystallography. Table 1 shows the 3 crystal data and structure refinement of EtSnCl TIFF2025518177000009.tif189170

[0130] Figure 4 shows the 3 1H-NMR of EtSnCl 3 (DME) recorded in CDCl 1 .

[0131] Example 3: Synthesis of EtSn(NMe 3 )(THF) using EtSnCl 2 (THF) 2 3

[0132] In a glove box filled with nitrogen, EtSnCl 3 (3.0 g, 11.8 mmol) was placed in a 40 mL vial and diluted with tetrahydrofuran (4 mL, 49.2 mmol), resulting in exotherm and presenting as a colorless solution. Separately, LiNMe 2 (1.89 g, 37.1 mmol) was placed in a 40 mL amber vial equipped with a magnetic stir bar and diluted with hexane (10 mL). After cooling to room temperature, the solution of EtSnCl 3 (THF) 2 was added dropwise to the LiNMe 2 mixture over 5 minutes with stirring, resulting in immediate exotherm and formation of a white precipitate. At that point, the resulting white mixture was stirred overnight.

[0133] The next morning, the reaction presented as a white mixture was filtered through a syringe filter, and the organic solution was dried under reduced pressure to obtain a pale yellow solid and a white solid. The concentrated C 6 D 6 solution recorded for the product 1 1H-, 13 13C-, and 119 ​​It was confirmed by Sn-NMR that the target molecule was synthesized with an initial purity of >98.5%. A long-term 119 Sn-NMR experiment was carried out to 2 Et 2 ) 2 (27.7 ppm) and Et 3 Sn(NMe 2 )(52.6 ppm) were 119 confirmed not to be detected by Sn-NMR.

[0134] Figure 5 shows the 6 CD 6 recorded Sn-NMR of EtSn(NMe 3 (THF) 2 synthesized from 2 ) 3 . 119

[0135] Example 4: Synthesis of EtSn(NMe 3 ) 2 using EtSnCl 3 (DME)

[0136] In a nitrogen-filled glove box, when EtSnCl 3 (3.0 g, 11.8 mmol) was added to dimethoxyethane (5 mL, 59.0 mmol), exotherm occurred and it was presented as a colorless solution. Separately, LiNMe 2 (1.89 g, 37.1 mmol) was placed in a 40 mL amber vial equipped with a magnetic stir bar and diluted with a 1:1 solution of DME / hexane (10 mL). After cooling to room temperature, the EtSnCl 3 (DME) solution was added dropwise to the LiNMe 2 mixture over 5 minutes with stirring, and exotherm and a white precipitate were immediately formed. At that point, the resulting white mixture was stirred overnight.

[0137] The next morning, the reactants were presented as a white mixture, and the solvent was removed under reduced pressure to produce a white matrix. The product was extracted with hexane (10 mL), and the resulting white mixture was filtered through a 0.2 μm syringe filter. The organic solution was dried under reduced pressure to obtain the product as a pale yellow liquid, and the product (1.44 g, 5.14 mmol) was isolated in a yield of 43.6%. The concentrated C of the product 6 D 6 recorded for the solution 1 H-, 13 C-, and 119 Sn-NMR confirmed that the target molecule was synthesized with an initial purity of >95%.

[0138] Figure 6 shows the 6 D 6 EtSnCl recorded in C 3 (DME)-synthesized EtSn(NMe 2 ) 3 of 119 Sn-NMR. A long-term Sn-NMR experiment collecting over 10,000 scans was carried out to confirm that Et 119 Sn-NMR did not detect Et 2 Sn(NMe 2 ) 2 (27.7 ppm) and Et 3 Sn(NMe 2 )(52.6 ppm). 119

[0139] Example 5: Synthesis of VinylSnCl 3 (DME)

[0140] Figure 7 shows the solid-state three-dimensional structure of vinylSnCl3(DME) determined by X-ray crystallography. Table 2 shows the crystal data and structure refinement of vinylSnCl 3 (DME). TIFF2025518177000010.tif189170

[0141] ​In a glove box filled with nitrogen, dimethoxyethane (DME) (2.6 g, 28.8 mmol) was placed in a 40 mL vial, and vinylSnCl 3 (2.0 g, 7.93 mmol) was added dropwise, immediately producing a white precipitate and heat. Crystals of X-ray quality were grown by cooling a saturated DME solution of vinylSnCl 3 (DME) to -35 °C.

[0142] Figure 8 shows the 3 Sn-NMR of vinylSnCl 119 (DME) recorded in DME. 119 Sn{ 1 H}-NMR (149 MHz, DME, 298 K): -381.7 ppm (impurity from starting vinylSnCl 3 at -291.6 ppm).

[0143] Example 6: Synthesis of VinylSn(NMe 3 (DME) using VinylSnCl 2 ) 3

[0144] In a glove box filled with nitrogen, vinylSnCl 3 (15 g, 59.4 mmol) was added dropwise to dimethoxyethane (15 mL, 144 mmol) in a 250 mL flask equipped with a stir bar. 50 mL of hexane was added to the flask to crash out the vinylSnCl3 adduct and make the mixture a suspension. LiNMe 2 (9.38 g, 184 mmol) solid was added portionwise over 3.5 hours. The resulting white mixture was stirred overnight.

[0145] Volatiles were removed under reduced pressure. The residue was extracted with hexane and filtered through a polypropylene (PP) frit filter. The organic solution was dried under reduced pressure to give the product as a pale yellow liquid. The concentrated C 6 D 6 solution recorded 119Sn-NMR showed a.

[0146] Example 7: Isopropenyl SnCl 3 (DME) synthesis

[0147] Figure 9, the three-dimensional structure of isopropenyl SnCl 3 (DME) in the solid state is shown. Table 3 shows the crystal data and structure refinement of isopropenyl SnCl 3 (DME). TIFF2025518177000011.tif189170

[0148] In a glove box filled with nitrogen, isopropenyl SnCl 3 (2.0 g, 7.51 mmol) was placed in a 40 mL vial and diluted with hexane (7 mL). Dimethoxyethane (1.73 g, 19.1 mmol) was added dropwise to the isopropenyl SnCl 3 solution, and a white precipitate immediately formed. After the addition of DME was complete, the vial was stirred at room temperature for 1 hour. Volatile substances were removed under reduced pressure, and the white solid was washed with hexane. Then, the remaining white solid was dried under reduced pressure. Mass: 2.63 g, (yield 97.7%). X-ray quality crystals were grown by cooling a saturated DME solution of isopropenyl SnCl 3 (DME) to -35 °C.

[0149] Figure 10 shows the 6 C 6 H-NMR of isopropenyl SnCl 3 (DME) recorded at 1 . 1 H-NMR (400 MHz, C 6 D 6, 298 K): 1.43 (s, 3H); 3.06 (s, 6H); 3.17 (s, 4H); 4.99 and 5.08 (s, 2H) ppm.

[0150] C 6 D 6 H-NMR of isopropenyl SnCl 3(DME) of 13 C-NMR. 13 C{ 1 H}-NMR (100 MHz, C 6 D 6, 298 K): 22.72; 58.73; 71.35; 131.34; 146.96 ppm.

[0151] C 6 D 6 Recorded isopropenyl SnCl 3 (DME) of 119 Sn-NMR. 119 Sn{ 1 H}-NMR (149 MHz, C 6 D 6, 298 K): -106.9 ppm.

[0152] Example 8: Synthesis of isopropenyl Sn(NMe 3 )(DME) using isopropenyl SnCl 2 ) 3 in

[0153] In a nitrogen-filled glove box, isopropenyl SnCl 3 (2.0 g, 7.51 mmol) was added to dimethoxyethane (5 mL, 59.0 mmol), and heat was generated, presenting as a white solid in the solution. The excess DME was removed under reduced pressure, and the solid was suspended in 10 mL of hexane. Separately, LiNMe 2 (1.14 g, 22.5 mmol) was placed in a 40 mL amber vial equipped with a magnetic stir bar and diluted with a 1:1 solution of THF / hexane (12 mL). While stirring the LiNMe 2 mixture, it was added dropwise to the isopropenyl SnCl 3 (DME) suspension, and heat generation and a white precipitate occurred. At that point, the resulting white mixture was stirred for 1 hour.

[0154] The reactants were presented as a pale yellow turbid mixture. The resulting mixture was filtered through a 0.2 μm syringe filter, and the organic solution was dried under reduced pressure to obtain the product as a pale yellow liquid. 1.4 g (4.79 mmol) was isolated in a yield of 63.9%. The concentrated C of the product 6 D 6 recorded for the solution 1 H-, 13 C-, and 119 Sn-NMR confirmed that the target molecule was synthesized with an initial purity of >85%.

[0155] Figure 11 shows the 6 D 6 Sn-NMR of isopropenyl SnCl 3 (DME) synthesized from (DME) in THF / hexane solvent recorded in C 2 )(DME) 3 of 119 which is shown.

[0156] Example 9: Synthesis of isopropenyl Sn(NMe 3 (DME) using isopropenyl SnCl 2 )(DME) 3 in

[0157] In a nitrogen-filled glove box, isopropenyl SnCl 3 (DME) adduct (2.6 g, 7.25 mmol) was dissolved in dimethoxyethane (5 mL, 59.0 mmol) in a 40 mL amber vial equipped with a stir bar. Separately, LiNMe 2 (1.13 g, 22.2 mmol) was suspended in a 1:1 solution of DME / hexane (10 mL). When the LiNMe 2 mixture was added dropwise to the isopropenyl SnCl 3 (DME) suspension with stirring, exotherm and a white precipitate occurred, at which point the resulting white mixture was stirred overnight.

[0158] The volatile substances were removed under reduced pressure. The residue was extracted with hexane and filtered through a polypropylene (PP) frit filter. The organic solution was dried under reduced pressure to obtain the product as a pale yellow liquid. 1.08 g (3.69 mmol) was isolated in a yield of 50.9%. The concentrated C of the product 6 D 6 recorded for the solution 1 H-, 13 C-, and 119 Sn-NMR confirmed that the target molecule was synthesized with an initial purity of >65%. Figure 12 shows the C 6 D 6 recorded for isopropenyl SnCl in DME / hexane solvent 3 (DME)-synthesized isopropenyl Sn(NMe 2 ) 3 of 119 Sn-NMR.

[0159] Example 10: Synthesis of isopropenyl Sn(NMe 3 (DME) using isopropenyl SnCl in hexane 2 ) 3

[0160] In a nitrogen-filled glove box, isopropenyl SnCl 3 (2.6 g, 7.25 mmol) in hexane (5 mL) was added to a 40 mL amber vial equipped with a stir bar, and LiNMe 2 (1.15 g, 22.7 mmol) was suspended in hexane (10 mL). Exotherm and formation of a white precipitate were observed, and the resulting mixture was stirred overnight.

[0161] The mixture was filtered through a polypropylene (PP) frit filter. The solid was further extracted with 5 mL of hexane solvent. The organic solution was dried under reduced pressure to obtain the product as a pale yellow liquid. 1.97 g (6.74 mmol) was isolated in a yield of 89.9%. The concentrated C 6 D 6 recorded for the solution 1 H-, 13 C-, and 119 ​It was confirmed by Sn-NMR that the target molecule was synthesized with an initial purity of >93%. Figure 13 is C 6 D 6 recorded in hexane solvent of isopropenyl SnCl 3 synthesized from isopropenyl Sn(NMe 2 ) 3 of 119 Sn-NMR is shown.

[0162] C 6 D 6 recorded in isopropenyl Sn(NMe 2 ) 3 of 119 Sn-NMR. 119 Sn{ 1 H}-NMR(149 MHz, C 6 D 6, 298 K): -87.4 ppm (1.0%), -99.6 ppm (93.1%), -119.0 ppm (5.9%).

[0163] Aspect

[0164] Various aspects will be described below. It should be understood that any one or more of the features described in the following aspects can be combined with any one or more of the other aspects.

[0165] Aspect 1. A method comprising obtaining a trihaloalkyltin, obtaining a solvent, a solution, or any combination thereof, and contacting the trihaloalkyltin with the solvent, the solution, or any combination thereof to form a trihaloalkyltin adduct.

[0166] Aspect 2. The method according to Aspect 1, wherein the method does not include forming a trihaloalkyltin-amine adduct.

[0167] Aspect 3. The method according to Aspect 1 or 2, wherein the trihaloalkyltin-amine adduct is a trihaloalkyltin-(HNMe 2 ) adduct.

[0168] Aspect 4. The trihaloalkyltin is a compound of the formula: RSnX 3 [wherein, R is a substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, and X is Cl, Br or I], the method according to any one of Aspects 1 to 3.

[0169] Aspect 5. R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 CF 2 HCH 2 CFH 2 CH 2 or CFH 2 , the method according to Aspect 4. In some aspects, the techniques described herein relate to methods in which R is an alkoxy.

[0170] Aspect 6. R is vinyl, allyl, propynyl, propenyl, or any isomer thereof, the method according to Aspect 4.

[0171] Aspect 7. The solvent contains at least one of tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof, the method according to any one of Aspects 1 to 6.

[0172] Aspect 8. The solution contains at least one of hexane, pentane, toluene, or any combination thereof, the method according to any one of Aspects 1 to 6.

[0173] Aspect 9. The method according to any one of Aspects 1 to 8, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0174] Aspect 10. The method according to any one of Aspects 1 to 9, wherein the trihaloalkyltin adduct is a compound of the formula: RSnX 3 ·(solv) n [wherein R is a substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, X is Cl, Br or I, solv is a solvent, and n is at least 1].

[0175] Aspect 11. A method comprising obtaining a trihaloalkyltin adduct, obtaining a lithium dialkylamide, and contacting the trihaloalkyltin adduct with the lithium dialkylamide to form a tris(dialkylamide)alkyltin product.

[0176] Aspect 12. The method according to Aspect 11, wherein the method does not include forming a trihaloalkyltin-amine adduct.

[0177] Aspect 13. The method according to aspect 12, wherein the trihaloalkyltin-amine adduct is a trihaloalkyltin-(HNMe 2 ) adduct.

[0178] Aspect 14. The trihaloalkyltin adduct is a compound of the formula: RSnX 3 ·(solv) n [wherein, R is a substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, X is Cl, Br or I, solv is a solvent, and n is at least 1], the method according to any one of aspects 11 to 13.

[0179] Aspect 15. The method according to aspect 14, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 、CF 2 HCH 2 、CFH 2 CH 2 、or CFH 2 . In some aspects, the techniques described herein relate to methods where R is an alkoxy.

[0180] Aspect 16. The method according to aspect 14, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0181] Aspect 17. The method according to Aspect 14, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, hexane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0182] Aspect 18. The method according to any one of Aspects 11 to 17, wherein the lithium dialkylamide is a compound of the formula: LiN(R 1 ) 2 [wherein R 1 is C 1 to C 3 alkyl].

[0183] Aspect 19. The method according to any one of Aspects 11 to 18, wherein the tris(dialkylamide)alkyltin product is a compound of the formula: TIFF2025518177000012.tif48170[wherein R is substituted C 1 to C 5 alkyl, unsubstituted C 1 to C 5 alkyl, substituted C 1 to C 5 alkenyl, or unsubstituted C 1 to C 5 alkenyl, and each R 1 is independently C 1 to C 3 alkyl].

[0184] Aspect 20. A method comprising obtaining a trihaloalkyltin, obtaining a solvent, a solution, or any combination thereof, contacting the trihaloalkyltin with the solvent, the solution, or any combination thereof to form a trihaloalkyltin adduct, obtaining a lithium dialkylamide, and contacting the trihaloalkyltin adduct with the lithium dialkylamide to form a tris(dialkylamide)alkyltin product.

[0185] Aspect 21. The method according to aspect 20, wherein the method does not include forming a trihaloalkyltin-amine adduct.

[0186] Aspect 22. The method according to aspect 21, wherein the trihaloalkyltin-amine adduct is a trihaloalkyltin-(HNMe 2 ) adduct.

[0187] Aspect 23. The trihaloalkyltin is a compound of the formula: RSnX 3 [wherein R is a substituted C 1 -C 5 alkyl, an unsubstituted C 1 -C 5 alkyl, a substituted C 1 -C 5 alkenyl, or an unsubstituted C 1 -C 5 alkenyl, and X is Cl, Br or I], the method according to any one of aspects 20 to 22.

[0188] Aspect 24. R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 , CF 2 HCH 2 , CFH 2 CH 2 , or CFH 2 . In some aspects, the techniques described herein relate to methods in which R is an alkoxy.

[0189] Aspect 25. The method according to aspect 23, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0190] Aspect 26. The method according to any one of aspects 20 to 25, wherein the solvent comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

[0191] Aspect 27. The method according to any one of aspects 20 to 26, wherein the solution comprises at least one of hexane, pentane, toluene, or any combination thereof.

[0192] Aspect 28. The method according to any one of aspects 20 to 27, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomer thereof, or any combination thereof.

[0193] Aspect 29. The trihaloalkyltin adduct has the formula: RSnX 3 ·(solv) n [wherein, R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5The method according to any one of embodiments 20 to 28, which is a compound where it is alkenyl, X is Cl, Br or I, solv is a solvent, and n is at least 1.

[0194] Embodiment 30. The lithium dialkylamide is of the formula: LiN(R 1 ) 2 [wherein R 1 is C 1 to C 3 alkyl-containing] The method according to any one of embodiments 20 to 29.

[0195] Embodiment 31. The tris(dialkylamide)alkyltin product is of the formula: TIFF2025518177000013.tif48170[wherein R is substituted C 1 to C 5 alkyl, unsubstituted C 1 to C 5 alkyl, substituted C 1 to C 5 alkenyl, or unsubstituted C 1 to C 5 alkenyl, and each R 1 is independently C 1 to C 3 alkyl] The method according to any one of embodiments 20 to 30.

[0196] Embodiment 32. A composition comprising a trihalogenated alkyltin adduct of the formula: RSnX 3 ·(solv) n [wherein R is substituted C 1 to C 5 alkyl, unsubstituted C 1 to C 5 alkyl, substituted C 1 to C 5 alkenyl, or unsubstituted C 1 to C 5 alkenyl, X is Cl, Br or I, solv is a solvent, and n is at least 1.

[0197] Aspect 33. The composition according to aspect 32, wherein the solvent comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), hexane, or any combination thereof.

[0198] Aspect 34. The composition according to aspect 32, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, hexane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0199] Aspect 35. A composition comprising a tris(dialkylamide)alkyltin product of the formula: TIFF2025518177000014.tif48170 [wherein R is a substituted C 1 ~C 5 alkyl, a substituted C 1 ~C 5 alkenyl, or an unsubstituted C 1 ~C 5 alkenyl, and each R 1 is independently a C 1 ~C 3 alkyl].

[0200] Aspect 36. R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 、CF 2 HCH 2 、CFH 2 CH 2、 or CFH 2 The composition according to embodiment 35, which is as described above. In some embodiments, the techniques described herein relate to methods in which R is an alkoxy group.

[0201] Embodiment 37. The composition according to embodiment 35, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0202] Embodiment 38. A composition comprising a reaction product of a trihaloalkyltin adduct and a lithium dialkylamide, the reaction product having the formula: TIFF2025518177000015.tif48170[wherein R is a substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, and each R 1 is independently C 1 ~C 5 alkyl] is a compound composition.

[0203] Embodiment 39. The composition according to embodiment 38, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 、 CF 2 HCH 2 、 CFH 2 CH 2 、 or CFH 2 is as described in embodiment 38.

[0204] Embodiment 40. The composition according to embodiment 38, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0205] Embodiment 41. Formula: RSnX 3 [wherein, R is a substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 is alkenyl, and X is Cl, Br, or I] atomic layer deposition precursor comprising a trihalogenated alkyltin adduct composition comprising the same.

[0206] Aspect 42. The composition according to Aspect 41, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 CF 2 HCH 2 CFH 2 CH 2 or CFH 2 is as described in Aspect 41.

[0207] Aspect 43. The composition according to Aspect 41, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0208] Aspect 44. Formula: RSnX 3 [wherein, R is a substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 is alkenyl, and X is Cl, Br, or I] chemical vapor deposition precursor comprising a trihalogenated alkyltin adduct composition comprising the same.

[0209] Aspect 45. R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF 3 CH 2 、CF 2 HCH 2 、CFH 2 CH 2 、 or CFH 2 and is the composition according to Aspect 44.

[0210] Aspect 46. R is vinyl, allyl, propynyl, propenyl, or any isomer thereof, and is the composition according to Aspect 44.

[0211] Aspect 47. Formula: TIFF2025518177000016.tif42170 [wherein, R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5 alkenyl, and R 2 is independently substituted C 1 ~C 4 alkyl or unsubstituted C 1 ~C 4 alkyl, and substituted C 1 ~C 4 alkyl contains a fluorine-containing substituent] of the compound and contains the composition.

[0212] Aspect 48. The C 2 of R 1 ~C 4 alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, or tert-butyl, and is the composition according to Aspect 47.

[0213] Aspect 49. The fluorine-containing substituent is -CH2 CF 3 、 -CH(CF 3 ) 2 、 or -(CH a ) n (CH b F c ) m and contains wherein: a = 0 to 3; b = 0 to 2; c = 1 to 3; n = 0 to 3; m = 1 to 4 is the composition according to embodiment 47.

[0214] Embodiment 50. -(CH a ) n (CH b F c ) m is -CH 2 F, -CH 2 CH 2 F, -CF 3 , or -CF 2 CF 3 is the composition according to embodiment 49.

[0215] Embodiment 51. R 2 is saturated alkyl or unsaturated alkyl, the composition according to embodiment 47.

[0216] Embodiment 52. OR 2 is -OCH 2 C≡CH or -OCH=CH 2 is the composition according to embodiment 47.

[0217] Embodiment 53. Formula: RSn(OR 2 ) 3 [wherein, R is substituted C 1 ~C 5 alkyl, unsubstituted C 1 ~C 5 alkyl, substituted C 1 ~C 5 alkenyl, or unsubstituted C 1 ~C 5is alkenyl, R 2 is, independently, substituted C 1 ~C 4 alkyl or unsubstituted C 1 ~C 4 alkyl, substituted C 1 ~C 4 alkyl contains a fluorine-containing substituent] compound composition comprising.

[0218] Aspect 54. R 2 of C 1 ~C 4 alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, or tert-butyl, the composition according to aspect 53.

[0219] Aspect 55. The fluorine-containing substituent is -CH 2 CF 3 , -CH(CF 3 ) 2 , or -(CH a ) n (CH b F c ) m and includes, wherein: a = 0 to 3; b = 0 to 2; c = 1 to 3; n = 0 to 3; m = 1 to 4 is, the composition according to aspect 53.

[0220] Aspect 56. -(CH a ) n (CH b F c ) m is -CH 2 F, -CH 2 CH 2 F, -CF 3 , or -CF 2 CF 3 is, the composition according to aspect 55.

[0221] Aspect 57.R 2 The composition according to aspect 53, wherein 2 is a saturated alkyl or an unsaturated alkyl.

[0222] Aspect 58.OR 2 is -OCH 2 C≡CH or -OCH=CH 2 The composition according to aspect 53, wherein 2 is -OCHC≡CH or -OCH=CH 2 .

[0223] It should be understood that changes may be made in detail, particularly with regard to the constituent materials used and the shape, size, and arrangement of the parts, without departing from the scope of the present disclosure. The present specification and the described embodiments are examples, and the true scope and spirit of the present disclosure are indicated by the appended claims.

Claims

1. obtaining a trihaloalkyltin; obtaining a solvent, a solution, or any combination thereof; contacting the trihaloalkyltin with a solvent, a solution, or any combination thereof to form a trihaloalkyltin adduct A method comprising:

2. The method according to claim 1, which does not include forming a trihaloalkyltin-amine adduct.

3. The method according to claim 2, wherein the trihaloalkyltin-amine adduct is a trihaloalkyltin-(HNM e ２ ). adduct).

4. The trihaloalkyltin is of the formula: RSnX ３ [wherein, R is a substituted C １ -C ５ alkyl, unsubstituted C １ -C ５ alkyl, substituted C １ -C ５ alkenyl, or unsubstituted C １ -C ５ alkenyl, and X is Cl, Br or I] is a compound of, the method according to claim 1.

5. R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF ３ CH ２ CF ２ HCH ２ CFH ２ CH ２ or CFH ２ and the method according to claim 4, wherein the method is as described above.

6. The method according to claim 4, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

7. The method according to claim 1, wherein the solvent comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

8. The method according to claim 1, wherein the solution comprises at least one of hexane, pentane, toluene, or any combination thereof.

9. The method according to claim 1, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

10. The trihaloalkyltin adduct is of the formula: RSnX ３ ・(solv) ｎ [wherein, R is a substituted C １ ~C ５ alkyl, an unsubstituted C １ ~C ５ alkyl, a substituted C １ ~C ５ alkenyl, or an unsubstituted C １ ~C ５ alkenyl, and X is Cl, Br or I; solv is a solvent; n is at least 1] is a compound of, the method according to claim 1.

11. obtaining a trihaloalkyltin adduct; obtaining a lithium dialkylamide; contacting the trihaloalkyltin adduct with the lithium dialkylamide to form a tris(dialkylamide)alkyltin product A method comprising:

12. The method according to claim 11, which does not include forming a trihaloalkyltin-amine adduct.

13. The method according to claim 12, wherein the trihaloalkyltin-amine adduct is a trihaloalkyltin-(HNM ２ e) adduct.

14. The trihaloalkyltin adduct is of the formula: RSnX ３ ・(solv) ｎ [wherein, R is a substituted C １ ~C ５ alkyl, unsubstituted C １ ~C ５ alkyl, substituted C １ ~C ５ alkenyl, or unsubstituted C １ ~C ５ alkenyl, and X is Cl, Br or I, solv is a solvent, n is at least 1] The method according to claim 11, which is a compound of.

15. R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF ３ CH ２ 、CF ２ HCH ２ 、CFH ２ CH ２ 、or CFH ２ and the method according to claim 14, wherein it is

16. The method according to claim 14, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

17. The solvent is acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, hexane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomer thereof, or at least one of any combination thereof. The method according to claim 14.

18. The lithium dialkylamide is of the formula: LiN(R １ ) ２ [wherein, R １ is C １ to C ３ alkyl-containing] The method according to claim 11, which is a compound of.

19. The tris(dialkylamide)alkyltin product is of the formula: [wherein, R is a substituted C １ -C ５ alkyl, unsubstituted C １ -C ５ alkyl, substituted C １ -C ５ alkenyl, or unsubstituted C １ -C ５ alkenyl, and Each R １ is independently C １ to C ３ alkyl] The method according to claim 11, which is a compound of.

20. Obtaining a trihaloalkyltin, Obtaining a solvent, solution, or any combination thereof, Contacting the trihaloalkyltin with a solvent, solution, or any combination thereof to form a trihaloalkyltin adduct, Obtaining a lithium dialkylamide, Contacting the trihaloalkyltin adduct with the lithium dialkylamide to form a tris(dialkylamide)alkyltin product A method comprising.

21. The method according to claim 20, wherein the method does not include forming a trihaloalkyltin-amine adduct.

22. The method according to claim 21, wherein the trihaloalkyltin-amine adduct is a trihaloalkyltin-(HNM ２ e ２ )-adduct.

23. The trihaloalkyltin is of the formula: RSnX ３ [wherein, R is a substituted C １ ~C ５ alkyl, unsubstituted C １ ~C ５ alkyl, substituted C １ ~C ５ alkenyl, or unsubstituted C １ ~C ５ alkenyl, and X is Cl, Br or I] The method according to claim 20, which is a compound of.

24. R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF ３ CH ２ 、CF ２ HCH ２ 、CFH ２ CH ２ 、or CFH ２ and the method according to claim 23

25. The method according to claim 23, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

26. The method according to claim 20, wherein the solvent comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

27. The method according to claim 20, wherein the solution comprises at least one of hexane, pentane, toluene, or any combination thereof.

28. The method according to claim 20, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomer thereof, or any combination thereof.

29. The trihaloalkyltin adduct is a compound of the formula: RSnX ３ ・(solv) ｎ [wherein, R is a substituted C １ ~C ５ alkyl, unsubstituted C １ ~C ５ alkyl, substituted C １ ~C ５ alkenyl, or unsubstituted C １ ~C ５ alkenyl, and X is Cl, Br or I; solv is a solvent; n is at least 1] The method according to claim 20.

30. The lithium dialkylamide is a compound of the formula: LiN(R １ ) ２ [wherein, R １ is C １ to C ３ alkyl-containing] The method according to claim 20.

31. The tris(dialkylamide)alkyltin product is a compound of the formula: [wherein, R is a substituted C １ -C ５ alkyl, unsubstituted C １ -C ５ alkyl, substituted C １ -C ５ alkenyl, or unsubstituted C １ -C ５ alkenyl, and Each R １ is independently C １ to C ３ alkyl] The method according to claim 20.

32. The formula: RSnX ３ ・(solv) ｎ [wherein, R is a substituted C １ -C ５ alkyl, an unsubstituted C １ -C ５ alkyl, a substituted C １ -C ５ alkenyl, or an unsubstituted C １ -C ５ alkenyl, and X is Cl, Br or I; solv is a solvent; n is at least 1] A composition comprising a trihaloalkyltin adduct.

33. The composition according to claim 32, wherein the solvent comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), hexane, or any combination thereof.

34. The composition according to claim 32, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, hexane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

35. Formula: [wherein, R is a substituted C １ -C ５ alkyl, substituted C １ -C ５ alkenyl, or unsubstituted C １ -C ５ alkenyl, and Each R １ is independently C １ to C ３ alkyl] A composition comprising a tris(dialkylamide)alkyltin product

36.

37. R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF ３ CH ２ 、CF ２ HCH ２ 、CFH ２ CH ２ 、or CFH ２ and is the composition according to claim 35. The composition according to claim 35, wherein R is vinyl, allyl, propynyl, propenyl, or any isomers thereof.

38. A composition comprising a reaction product of an alkyltin trihalide adduct and a lithium dialkylamide, wherein the reaction product is a compound of the formula:

39. [wherein, R is a substituted C １ -C ５ alkyl, unsubstituted C １ -C ５ alkyl, substituted C １ -C ５ alkenyl, or unsubstituted C １ -C ５ alkenyl, and Each R １ is independently C １ to C ５ alkyl]

40. The composition according to claim 38, wherein R is vinyl, allyl, propynyl, propenyl, or any isomers thereof. R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF ３ CH ２ 、CF ２ HCH ２ 、CFH ２ CH ２ 、or CFH ２ and is the composition according to claim 38.

41. Formula: [wherein a composition comprising an atomic layer deposition precursor comprising an alkyltin trihalide of RSnX ３

42. R is a substituted C １ -C ５ alkyl, unsubstituted C １ -C ５ alkyl, substituted C １ -C ５ alkenyl, or unsubstituted C １ -C ５ alkenyl, and X is Cl, Br or I]

43. The composition according to claim 41, wherein R is vinyl, allyl, propynyl, propenyl, or any isomers thereof.

44. R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF ３ CH ２ 、CF ２ HCH ２ 、CFH ２ CH ２ 、or CFH ２ and the composition according to claim 41 Formula: a composition comprising a chemical vapor deposition precursor comprising an alkyltin trihalide of

45.

46. RSnX ３ [wherein, R is a substituted C １ -C ５ alkyl, unsubstituted C １ -C ５ alkyl, substituted C １ -C ５ alkenyl, or unsubstituted C １ -C ５ alkenyl, and X is Cl, Br or I] The composition according to claim 44, wherein R is vinyl, allyl, propynyl, propenyl, or any isomers thereof.

47. Formula: R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, t-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF ３ CH ２ 、CF ２ HCH ２ 、CFH ２ CH ２ 、or CFH ２ and the composition according to claim 44, wherein the composition is as defined above. [wherein a composition comprising a compound of

48.

49. In the formula: R is a substituted C １ ~C ５ alkyl, an unsubstituted C １ ~C ５ alkyl, a substituted C １ ~C ５ alkenyl, or an unsubstituted C １ ~C ５ alkenyl, and R ２ is, independently, a substituted C １ -C ４ alkyl or an unsubstituted C １ -C ４ alkyl, and Replacement C １ ~C ４ The alkyl group contains a fluorine-containing substituent] a = 0 to 3; b = 0 to 2; R ２ of C １ -C ４ The composition according to claim 47, wherein the alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, or tert-butyl. c = 1 to 3; The fluorine-containing substituent is -CH ２ CF ３ , -CH(CF ３ ) ２ , or -(CH ａ ) ｎ (CH ｂ F ｃ ) ｍ and includes n = 0 to 3; m = 1 to 4 The composition according to claim 47.

50.

51.

52.

53. Formula: -(CH ａ ) ｎ (CH ｂ F ｃ ) ｍ is -CH ２ F, -CH ２ CH ２ F, -CF ３ , or -CF ２ CF ３ and is the composition according to claim 49. [wherein R ２ The composition according to claim 47, wherein R is a saturated alkyl or an unsaturated alkyl. a composition comprising a compound of OR ２ is -OCH ２ C≡CH or -OCH=CH ２ The composition according to claim 47, wherein it is such.

54.

55. RSn(OR ２ ) ３ In the formula: R is a substituted C １ ~C ５ alkyl, an unsubstituted C １ ~C ５ alkyl, a substituted C １ ~C ５ alkenyl, or an unsubstituted C １ ~C ５ alkenyl, and R ２ is, independently, substituted C １ -C ４ alkyl or unsubstituted C １ -C ４ alkyl, and Replacement C １ ~C ４ The alkyl group contains a fluorine-containing substituent] a = 0 to 3; b = 0 to 2; R ２ of C １ to C ４ The composition according to claim 53, wherein the alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, or tert-butyl. c = 1 to 3; The fluorine-containing substituent is -CH ２ CF ３ , -CH(CF ３ ), or -(CH ２ ), or -(CH ａ )(CH ｎ )(CH ｂ F ｃ ), and ｍ includes n = 0 to 3; ​ ​ ​ ​ m = 1 to 4 The composition according to claim 53, wherein Claim 56 -(CH ａ ) ｎ (CH ｂ F ｃ ) ｍ is -CH ２ F, -CH ２ CH ２ F, -CF ３ , or -CF ２ CF ３ and the composition according to claim 55 Claim 57 R ２ The composition according to claim 53, wherein R is a saturated alkyl or an unsaturated alkyl. Claim 58 OR ２ is - OCH ２ C≡CH or - OCH = CH ２ The composition according to claim 53, wherein the composition is as described above.

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