Compositions of alkyltin trihalide and related methods

Abstract

The present disclosure includes a method of obtaining an alkyltin trihalide, obtaining a solvent, and contacting the alkyltin trihalide with the solvent to form an alkyltin trihalide adduct. Also described is a composition comprising: an alkyltin trihalide adduct of the formula RSnX3. (solv) n wherein: R is a substituted C1-C5 alkyl group, an unsubstituted C1-C5 alkyl group, a substituted C1-C5 alkenyl group, or an unsubstituted C1-C5 alkenyl group; x is Cl, Br or I; solv is used as a solvent; and n is at least 1.

Description

Technical Field

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

[0002] priority

[0003] The present disclosure claims priority to U.S. Provisional Patent No. 63 / 348,859, filed on June 3, 2022, and U.S. Provisional Patent No. 63 / 400,269, filed on August 23, 2022. Both priority documents are incorporated herein by reference. Background Art

[0004] Thin films can be used in applications during the manufacture of microelectronic devices. Some thin films can be produced using chemical vapor deposition or atomic layer deposition. Summary of the invention

[0005] The present disclosure is directed to alkyltin trihalide adducts, including solvent-based alkyltin trihalide adducts, which are used to make 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 with low to no dialkyl impurities, such as tris(dimethylamino)tin alkyl compounds.

[0006] The present disclosure solves the problem of producing high purity tris(dimethylamino)alkyltin compounds with low to zero content of dialkyl impurities. In addition, the present disclosure requires very few steps to synthesize the compounds and requires low cost to produce the compounds.

[0007] The present disclosure describes a direct route to prepare RSn(NMe2)3. In some embodiments and as further described herein, R may be isopropenyl, isopropyl, or ethyl. The solvent-based route allows the present disclosure to avoid the need to prepare HNMe2 adducts of RSnCl3 compounds to reduce the impurity profile of R2Sn(NMe2)2.

[0008] The synthesis is R group and solvent / solvent dependent. Solvent / solvent selection (e.g., tetrahydrofuran (THF), dimethoxyethane (DME), or hexanes) is a factor in providing the final product in appropriate yield and purity.

[0009] The present disclosure uses a coordinating solvent to form a separable alkyltin trichloride adduct alkylSnCl3(solv) 1-2 , which effectively provides a synthon for producing the desired tris(dimethylamino)alkyltin product of interest in high purity. The disclosed method requires fewer reagents and steps to make the alkyltin trichloride adduct than current processes, and thus presents a faster and cheaper process.

[0010] In some aspects, the technology described herein relates to a method comprising: obtaining an alkyltin trihalide; obtaining a solvent, a solution, or any combination thereof; and contacting the alkyltin trihalide with the solvent, the solution, or any combination thereof to form an alkyltin trihalide adduct.

[0011] In some aspects, the technology described herein relates to a method wherein the method does not include forming an alkyltin trihalide-amine adduct.

[0012] In some aspects, the technology described herein relates to a method wherein the alkyltin trihalide-amine adduct is an alkyltin trihalide-(HNMe2) adduct.

[0013] In some aspects, the technology described herein relates to a method wherein the alkyltin trihalide is a compound of the formula: RSnX3, wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; and X is Cl, Br, or I.

[0014] In some aspects, the technology described herein relates to a method wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2. In some aspects, the technology described herein relates to a method wherein R is alkoxy.

[0015] In some aspects, the technology described herein relates to a method wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0016] In some aspects, the technology described herein relates to a method wherein the solvent comprises at least one of: tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

[0017] In some aspects, the technology described herein relates to a method wherein the solution includes at least one of: hexane, pentane, toluene, or any combination thereof.

[0018] In some aspects, the technology described herein relates to a method wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0019] In some aspects, the technology described herein relates to a method wherein the alkyltin trihalide adduct is a compound of the formula: RSnX3·(solv) n , wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; X is Cl, Br, or I; solv is a solvent; and n is at least 1.

[0020] In some aspects, the technology described herein relates to a method comprising: obtaining an alkyltin trihalide adduct; obtaining a lithium dialkylamide; and contacting the alkyltin trihalide adduct with the lithium dialkylamide to form a tris(dialkylamido)alkyltin product.

[0021] In some aspects, the technology described herein relates to a method wherein the method does not include forming an alkyltin trihalide-amine adduct.

[0022] In some aspects, the technology described herein relates to a method wherein the alkyltin trihalide-amine adduct is an alkyltin trihalide-(HNMe2) adduct.

[0023] In some aspects, the technology described herein relates to a method wherein the alkyltin trihalide adduct is a compound of the formula: RSnX3·(solv) n , wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; X is Cl, Br, or I; solv is a solvent; and n is at least 1.

[0024] In some aspects, the technology described herein relates to a method wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2. In some aspects, the technology described herein relates to a method wherein R is alkoxy.

[0025] In some aspects, the technology described herein relates to a method wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0026] In some aspects, the technology described herein relates to a method wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, hexane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0027] In some aspects, the technology described herein relates to a method wherein the lithium dialkylamide is a compound of the formula: LiN(R 1 )2, where: R 1 Including C1-C3 alkyl.

[0028] In some aspects, the technology described herein relates to a method wherein the tri(dialkylamido)alkyltin product is a compound of the formula:

[0029]

[0030] wherein R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; and wherein each R 1 are independently C1-C3 alkyl.

[0031] In some aspects, the technology described herein relates to a method comprising: obtaining an alkyltin trihalide; obtaining a solvent, a solution, or any combination thereof; and contacting the alkyltin trihalide with the solvent, the solution, or any combination thereof to form an alkyltin trihalide adduct; obtaining a lithium dialkylamide; and contacting the alkyltin trihalide adduct with the lithium dialkylamide to form a tris(dialkylamido)alkyltin product.

[0032] In some aspects, the technology described herein relates to a method wherein the method does not include forming an alkyltin trihalide-amine adduct.

[0033] In some aspects, the technology described herein relates to a method wherein the alkyltin trihalide-amine adduct is an alkyltin trihalide-(HNMe2) adduct.

[0034] In some aspects, the technology described herein relates to a method wherein the alkyltin trihalide is a compound of the formula: RSnX3, wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; and X is Cl, Br, or I.

[0035] In some aspects, the technology described herein relates to a method wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2. In some aspects, the technology described herein relates to a method wherein R is alkoxy.

[0036] In some aspects, the technology described herein relates to a method wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0037] In some aspects, the technology described herein relates to a method wherein the solvent comprises at least one of: tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

[0038] In some aspects, the technology described herein relates to a method wherein the solution includes at least one of: hexane, pentane, toluene, or any combination thereof.

[0039] In some aspects, the technology described herein relates to a method wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0040] In some aspects, the technology described herein relates to a method wherein the alkyltin trihalide adduct is a compound of the formula: RSnX3·(solv) n , wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; X is Cl, Br, or I; solv is a solvent; and n is at least 1.

[0041] In some aspects, the technology described herein relates to a method wherein the lithium dialkylamide is a compound of the formula: LiN(R 1)2, where: R 1 Including C1-C3 alkyl.

[0042] In some aspects, the technology described herein relates to a method wherein the tri(dialkylamido)alkyltin product is a compound of the formula:

[0043]

[0044] wherein R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; wherein each R 1 are independently C1-C3 alkyl.

[0045] In some aspects, the technology described herein relates to a composition comprising: an alkyltin trihalide adduct of the formula: RSnX3·(solv) n , wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; X is Cl, Br, or I; solv is a solvent; and n is at least 1.

[0046] In some aspects, the technology described herein relates to a composition wherein the solvent comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), hexane, or any combination thereof.

[0047] In some aspects, the technology described herein relates to a composition wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, hexane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0048] In some aspects, the technology described herein relates to a composition comprising: a tri(dialkylamido)alkyltin product of the formula:

[0049]

[0050] wherein R is a substituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; wherein each R 1 are independently C1-C3 alkyl.

[0051] In some aspects, the technology described herein relates to a composition, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2. In some aspects, the technology described herein relates to a method, wherein R is alkoxy.

[0052] In some aspects, the technology described herein relates to a composition wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0053] In some aspects, the technology described herein relates to a composition comprising: a reaction product of an alkyltin trihalide adduct and a lithium dialkylamide, wherein the reaction product comprises a compound of the formula:

[0054]

[0055] wherein R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; wherein each R 1 are independently C1-C5 alkyl.

[0056] In some aspects, the technology described herein relates to a composition, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2. In some aspects, the technology described herein relates to a method, wherein R is alkoxy.

[0057] In some aspects, the technology described herein relates to a composition wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0058] In some aspects, the technology described herein relates to a composition comprising an atomic layer deposition precursor comprising an alkyl tin trihalide of the formula: RSnX3, wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; and X is Cl, Br, or I.

[0059] In some aspects, the technology described herein relates to a composition wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2, or CFH2.

[0060] In some aspects, the technology described herein relates to a composition wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0061] In some aspects, the technology described herein relates to a composition comprising a chemical vapor deposition precursor comprising an alkyl tin trihalide of the formula: RSnX3, wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; and X is Cl, Br, or I.

[0062] In some aspects, the technology described herein relates to a composition wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2, or CFH2.

[0063] In some aspects, the technology described herein relates to a composition wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0064] In some aspects, the technology described herein relates to a composition comprising a compound of the formula:

[0065]

[0066] in:

[0067] R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl;

[0068] R 2 is independently a substituted C1-C4 alkyl group or an unsubstituted C1-C4 alkyl group, wherein the substituted C1-C4 alkyl group contains a fluorine-containing substituent.

[0069] In some aspects, the technology described herein relates to a composition wherein R 2 The C1-C4 alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

[0070] In some aspects, the technology described herein relates to a composition wherein the fluorine-containing substituent comprises -CH2CF3, -CH(CF3)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.

[0071] In some aspects, the technology described herein relates to a composition wherein -(CH a ) n (CH b F c ) m It is -CH2F, -CH2CH2F, -CF3 or -CF2CF3.

[0072] In some aspects, the technology described herein relates to a composition wherein R 2 It is a saturated alkyl group or an unsaturated alkyl group.

[0073] In some aspects, the technology described herein relates to a composition wherein OR 2 It is -OCH2C≡CH or -OCH=CH2.

[0074] In some aspects, the technology described herein relates to a composition comprising a compound of the formula: RSn(OR 2 )3, wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; R 2 is independently a substituted C1-C4 alkyl group or an unsubstituted C1-C4 alkyl group, wherein the substituted C1-C4 alkyl group contains a fluorine-containing substituent.

[0075] In some aspects, the technology described herein relates to a composition wherein R 2 The C1-C4 alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

[0076] In some aspects, the technology described herein relates to a composition wherein the fluorine-containing substituent comprises -CH2CF3, -CH(CF3)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.

[0077] In some aspects, the technology described herein relates to a composition wherein -(CH a ) n (CH b F c ) m It is -CH2F, -CH2CH2F, -CF3 or -CF2CF3.

[0078] In some aspects, the technology described herein relates to a composition wherein R 2It is a saturated alkyl group or an unsaturated alkyl group.

[0079] In some aspects, the technology described herein relates to a composition wherein OR 2 It is -OCH2C≡CH or -OCH=CH2. BRIEF DESCRIPTION OF THE DRAWINGS

[0080] As an example only, some embodiments of the present disclosure are described herein with reference to the accompanying drawings. With specific reference now to the drawings in detail, it should be emphasized that the embodiments shown are by way of example and for the purpose of illustrative discussion of the embodiments of the present disclosure. In this regard, the description in conjunction with the drawings makes it apparent to those skilled in the art how the embodiments of the present disclosure may be practiced.

[0081] Figure 1 Non-limiting examples of the methods of the present disclosure are depicted herein.

[0082] Figure 2 Shows the recorded EtSnCl3(THF)2 in CDCl3 1 H-NMR.

[0083] Figure 3 Shown is the solid-state 3D structure of EtSnCl3(DME) as determined by X-ray crystallography.

[0084] Figure 4 Shows the EtSnCl3(DME) recorded in CDCl3 1 H-NMR.

[0085] Figure 5 Showing the synthesis of EtSn(NMe2)3 from EtSnCl3(THF)2 recorded in C6D6 119 Sn-NMR.

[0086] Figure 6 Shows the synthesis of EtSn(NMe2)3 from EtSnCl3(DME) recorded in C6D6 119 Sn-NMR.

[0087] Figure 7 Shown is the solid-state 3D structure of vinyl SnCl3(DME) as determined by X-ray crystallography.

[0088] Figure 8 Shows the vinyl SnCl3 (DME) recorded in DME 119 Sn-NMR.

[0089] Fig. 9 Shown is the solid-state 3D structure of isopropenylSnCl3(DME) as determined by X-ray crystallography.

[0090] Fig.10 Shows the isopropenyl SnCl3 (DME) recorded in C6D6 1 H-NMR.

[0091] Fig.11 The synthesis of isopropenyl Sn(NMe2)3 from isopropenyl SnCl3(DME) in THF / hexane solvent recorded in C6D6 is shown. 119 Sn-NMR.

[0092] Fig.12 Shows the synthesis of isopropenyl Sn(NMe2)3 from DME / hexane solvent containing isopropenyl SnCl3(DME) recorded in C6D6 119 Sn-NMR.

[0093] Fig.13 The synthesis of isopropenyl Sn(NMe2)3 from hexane solvent containing isopropenyl SnCl3 recorded in C6D6 is shown. 119 Sn-NMR. DETAILED DESCRIPTION

[0094] Among those benefits and improvements disclosed, other objects and advantages of the present disclosure will become apparent from the following description in conjunction with the accompanying drawings. Detailed embodiments of the present disclosure are disclosed herein; however, it should be understood that the disclosed embodiments are merely illustrative of the present disclosure that can be embodied in various forms. In addition, each of the examples given with respect to the various embodiments of the present disclosure is intended to be illustrative rather than restrictive.

[0095] All prior patents and publications referenced herein are incorporated by reference in their entirety.

[0096] Throughout this specification and claims, unless the context clearly dictates otherwise, the following terms adopt the meanings explicitly associated herein. As used herein, the phrases "in one embodiment," "in an embodiment," and "in some embodiments" do not necessarily refer to the same embodiment, but they may refer to the same embodiment. In addition, as used herein, "in another embodiment" and "in some other embodiments" do not necessarily refer to different embodiments, but they may refer to different embodiments. All embodiments of the present disclosure are intended to be combined without departing from the scope or spirit of the present disclosure.

[0097] As used herein, unless the context clearly dictates otherwise, the term "based on" is not exclusive and allows for being based on additional factors not described. In addition, throughout this specification, the meaning of "a / an" and "the" includes plural references. The meaning of "in" includes "in" and "on".

[0098] Figure 1 A non-limiting embodiment of the method 100 of the present disclosure described herein is depicted. The method 100 includes one or more of the following steps. A first step 110 includes obtaining an alkyltin trihalide. A second step 120 includes obtaining a solvent, a solution, or any combination thereof. A third step 130 includes contacting the alkyltin trihalide with a solvent, a solution, or any combination thereof to form an alkyltin trihalide adduct. A fourth step 140 includes obtaining an alkyltin trihalide adduct. A fifth step 150 includes obtaining a lithium dialkylamide. A sixth step 160 includes contacting the alkyltin trihalide adduct with a lithium dialkylamide to form a tri(dialkylamido)alkyltin product.

[0099] The method 100 may include any combination of the steps. For example, in some embodiments, the method 100 may be a first step 110, a second step 120, and a third step 130. In some embodiments, the method 100 may be a fourth step 140, a fifth step 150, and a sixth step 160. In some embodiments, the method 100 may be a first step 110, a second step 120, and a third step 130, a fourth step 140, a fifth step 150, and a sixth step 160.

[0100] In some embodiments, method 100 does not include forming an alkyltin trihalide-amine adduct. In some embodiments, the alkyltin trihalide-amine adduct is an alkyltin trihalide-(HNMe2) adduct. For example, in some embodiments, the alkyltin trihalide-(HNMe2) adduct has two amines-(HNMe2)2.

[0101] The present disclosure is directed to alkyltin trihalide adducts (including solvent-based alkyltin trihalide adducts) for use in making high purity (e.g., greater than 95% purity) extreme ultraviolet atomic layer deposition precursors. 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%.

[0102] In some embodiments, the alkyltin trihalide (e.g., see first step 110) is a compound of formula RSnX3. In some embodiments, R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, an unsubstituted C1-C5 alkenyl, a substituted C1-C5 alkynyl, or an unsubstituted C1-C5 alkynyl. In some embodiments, X is Cl, Br, or I.

[0103] In some embodiments, the solvent (eg, see second step 120 ) includes at least one of tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

[0104] In some embodiments, the solution (eg, see second step 120 ) includes at least one of: hexane, pentane, toluene, or any combination thereof.

[0105] In some embodiments, the solvent includes at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0106] In some embodiments, the alkyltin trihalide adduct (eg, see third step 130 and / or fourth step 140) is of the formula RSnX3·(solv) n In some embodiments, R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl. X is Cl, Br, or I. In some embodiments, solv is a solvent. In some embodiments, n is at least 1.

[0107] In some embodiments, the lithium dialkylamide (eg, see fifth step 150) is of the formula LiN(R 1 )2. In some embodiments, R 1 It is a C1-C3 alkyl group.

[0108] In some embodiments, the present disclosure includes a composition including a tris(dialkylamido)alkyltin product (eg, see sixth step 160).

[0109] In some embodiments, the present disclosure includes a composition including the reaction product of an alkyltin trihalide adduct and a lithium dialkylamide.

[0110] In some embodiments, the tris(dialkylamido)alkyltin product (eg, see sixth step 160) is a compound of the formula:

[0111]

[0112] In some embodiments, R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2, CFH2, or alkoxy.

[0113] In some embodiments, R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0114] In some embodiments, R is a substituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl. 1 are independently C1-C3 alkyl.

[0115] In some embodiments, each R and each R 1 can be independently selected from a straight chain or branched alkyl group, including methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl or sec-pentyl. In a specific embodiment, each R and each R 1 is independently selected from a C1-C3 alkyl group, such as a methyl, ethyl or propyl group. 1 is selected from C1-C5 alkyl, which may be a substituted or unsubstituted straight chain or branched alkyl. For example, R or R 1 It can be a straight chain or branched alkyl group, including methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl or sec-pentyl. 1 It may be a cyclic C1-C5 group, such as a cyclopropyl group. 1 It may be an unsaturated C1-C5 group, such as vinyl or ethynyl. 1 Any of the groups may be further substituted, for example, by one or more halogen groups or ether groups. 1 It may be a compound 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, including monofluorinated C1-C5 alkyl groups (e.g., -CH2F or -CH2CH2F groups) and perfluorinated C1-C5 groups (e.g., -CF3 or -CF2CF3 groups). Alternatively, R or R 1It may be an alkyl ether group, wherein the alkyl portion is a C1-C5 alkyl group. 1 It is methyl, ethyl or isopropyl.

[0116] In some embodiments, R or R 1 It may be an alkyl, alkenyl, alkynyl, alkoxide, carboxylate, ether, nitrile or imide.

[0117] In some embodiments, R or R 1 It may be a C1-C5 alkyl group (methyl, ethyl, n-propyl, isopropyl, cyclopropyl, sec-butyl, n-butyl, tert-butyl, isopentyl, cyclopentadienyl, vinyl, ethynyl, propynyl, isopropenyl or acetyl).

[0118] In some embodiments, R or R 1 Can be C6-C n Phenyl, including substituted phenyl or substituted substituted cyclopentadienyl (eg, indene).

[0119] In some embodiments, R or R 1 It may be a functionalized alkyl group, including -CF3, -CF2H, -CFH2, CF3CH2, CF2HCH2, CFH2CH2, ICH2CH2 (ethyl iodide), CH3OCH2, CH3CH2OCH2-, CH3CH2OCH2CH2-, CH3OCH2CH2- or -C≡N.

[0120] In some embodiments, R or R 1 It may be a carboxylic acid ester, including CF3CO2 (trifluoroacetate) or CH3CO2 (acetate).

[0121] In some embodiments, R or R 1 Can be alcohol salt (CX n H 3-n CX m H 2-m O-, wherein X = F, Cl, Br, I, and n, m = 0-3). For example, R or R 1 It can be CF3CH2O-(trifluoroethanolate), CH3O-(methoxide), CH3CH2O-(ethanolate), (CH3)2CHO-(isopropoxide), (CH3)3CO-(tert-butoxide) or HC≡CO-(propargyloxide).

[0122] In some embodiments, R or R 1 Any combination of compounds described in the present disclosure (eg, fluoroethers or fluoroalkoxides) may be used.

[0123] Some embodiments relate to a composition. In some embodiments, the composition comprises an atomic layer deposition precursor comprising an alkyltin trihalide of the formula: RSnX3.

[0124] In some embodiments, R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl. In some embodiments, X is Cl, Br or I.

[0125] In some embodiments, R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2, or CFH2.

[0126] In some embodiments, R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0127] Some embodiments relate to a composition. In some embodiments, the composition comprises a chemical vapor deposition precursor comprising an alkyltin trihalide of the formula: RSnX3.

[0128] In some embodiments, R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl. In some embodiments, X is Cl, Br or I.

[0129] In some embodiments, R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2, or CFH2.

[0130] In some embodiments, R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0131] Some embodiments relate to a composition comprising a compound of the formula:

[0132]

[0133] In some embodiments, R is substituted C1-C5 alkyl, unsubstituted C1-C5 alkyl, substituted C1-C5 alkenyl, or unsubstituted C1-C5 alkenyl.

[0134] In some embodiments, R 2 is independently a substituted C1-C4 alkyl or an unsubstituted C1-C4 alkyl. In some embodiments, the substituted C1-C4 alkyl comprises a fluorine-containing substituent.

[0135] In some embodiments, R 2The C1-C4 alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

[0136] In some embodiments, the fluorine-containing substituent comprises -CH2CF3, -CH(CF3)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.

[0137] In some embodiments, -(CH a ) n (CH b F c ) m It is -CH2F, -CH2CH2F, -CF3 or -CF2CF3.

[0138] In some embodiments, R 2 It is a saturated alkyl group or an unsaturated alkyl group.

[0139] In some embodiments, OR 2 It is -OCH2C≡CH or -OCH=CH2.

[0140] Some embodiments relate to a composition comprising a compound of the formula: RSn(OR 2 )3.

[0141] In some embodiments, R is substituted C1-C5 alkyl, unsubstituted C1-C5 alkyl, substituted C1-C5 alkenyl, or unsubstituted C1-C5 alkenyl.

[0142] In some embodiments, R 2 is independently a substituted C1-C4 alkyl or an unsubstituted C1-C4 alkyl. In some embodiments, the substituted C1-C4 alkyl comprises a fluorine-containing substituent.

[0143] In some embodiments, R 2 The C1-C4 alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

[0144] In some embodiments, the fluorine-containing substituent comprises -CH2CF3, -CH(CF3)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.

[0145] In some embodiments, -(CH a ) n (CH b F c ) m It is -CH2F, -CH2CH2F, -CF3 or -CF2CF3.

[0146] In some embodiments, R 2 It is a saturated alkyl group or an unsaturated alkyl group.

[0147] In some embodiments, OR 2 It is -OCH2C≡CH or -OCH=CH2.

[0148] Examples

[0149] Example 1: Synthesis of EtSnCl3(THF)2

[0150] In a nitrogen-filled glove box, EtSnCl (0.500 g, 1.96 mmol) was placed in a 40 mL vial and diluted with hexane (2 mL). Tetrahydrofuran (0.71 g, 9.84 mmol) was added dropwise to the EtSnCl solution, causing a white precipitate to be produced immediately. After complete addition of THF, the vial was placed in a freezer at -35 ° C for 1 hour, the mother liquor was drawn off, and the remaining white solid was warmed to room temperature and dried under reduced pressure. After heating, the product melted to form a colorless liquid. Quality: 3.12 g, 99.7% yield. 1 H-NMR (400MHz, CDCl3, 298K): 1.32(t,3H); 1.74(t,8H); 2.13(q,2H); 3.67(t,8H)ppm; 13 C{ 1 H}-NMR (100MHz, CDCl3, 298K): 9.46; 25.07; 29.20; 68.32ppm; 119 Sn{ 1 H}-NMR (149MHz, CDCl3, 298K): -150.98ppm.

[0151] Figure 2 Shows the recorded EtSnCl3(THF)2 in CDCl3 1 H-NMR.

[0152] Example 2: Synthesis of EtSnCl3(DME)

[0153] In a nitrogen filled glove box, EtSnCl3 (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 EtSnCl3 solution, causing an immediate white precipitate to form. After complete addition of DME, the vial was placed in a freezer at -35°C for 1 hour, the mother liquor was drawn off, and the remaining white solid was warmed to room temperature and dried under reduced pressure. Mass: 2.70 g, 98.8% yield. MP: 61.9°C (by DSC). X-ray quality crystals were grown by cooling a saturated DME solution of EtSnCl3 (DME) at -35°C. 1 H-NMR (400MHz, CDCl3, 298K): 1.46 (t, 3H); 2.28 (q, 2H); 3.39 (s, 6H); 3.56 (s, 4H) ppm; 13 C{ 1 H}-NMR (100MHz, CDCl3, 298K): 9.54; 28.22; 59.26; 71.44ppm; 119 Sn{ 1 H}-NMR (149MHz, CDCl3, 298K): -49.63ppm.

[0154] Figure 3 The solid-state 3D structure of EtSnCl3(DME) as determined by X-ray crystallography is shown in Table 1. The crystal data and structure refinement of EtSnCl3(DME) are shown in Table 1.

[0155] Table 1: Crystallographic data and structure refinement of EtSnCl3(DME).

[0156]

[0157]

[0158] Figure 4 Shows the EtSnCl3(DME) recorded in CDCl3 1 H-NMR.

[0159] Example 3: Synthesis of EtSn(NMe2)3 using EtSnCl3(THF)2

[0160] In a nitrogen-filled glove box, EtSnCl (3.0 g, 11.8 mmol) was placed in a 40 mL vial and diluted with tetrahydrofuran (4 mL, 49.2 mmol), causing an exotherm and appearing as a colorless solution. Separately, LiNMe (1.89 g, 37.1 mmol) was placed in a 40 mL amber vial equipped with a magnetic stir bar and diluted with hexanes (10 mL). After cooling to room temperature, the EtSnCl (THF) solution was added dropwise to the LiNMe mixture under stirring over the course of 5 minutes, causing an exotherm and producing a white precipitate, at which point the resulting white mixture was stirred overnight.

[0161] The next morning, the reaction, which appeared as a white mixture, was filtered through a syringe filter and the organic solution was dried under reduced pressure to obtain a light yellow solid and a white solid. 1 H-, 13 C- and 119 Sn-NMR confirmed that the target molecule had been synthesized with >98.5% initial purity. Long-term analysis with over 10,000 scans collected 119 Sn-NMR experiments were performed to confirm that Et2Sn(NMe2)2 (27.7 ppm) and Et3Sn(NMe2) (52.6 ppm) were not 119 Sn-NMR detected.

[0162] Figure 5 Showing the synthesis of EtSn(NMe2)3 from EtSnCl3(THF)2 recorded in C6D6 119 Sn-NMR.

[0163] Example 4: Synthesis of EtSn(NMe2)3 using EtSnCl3(DME)

[0164] In a nitrogen-filled glove box, EtSnCl3 (3.0 g, 11.8 mmol) was added to dimethoxyethane (5 mL, 59.0 mmol), causing an exotherm and a colorless solution to appear. Separately, LiNMe2 (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 EtSnCl3 (DME) solution was added dropwise to the LiNMe2 mixture under stirring over the course of 5 minutes, causing an exotherm and the production of a white precipitate, at which point the resulting white mixture was stirred overnight.

[0165] The next morning, the reaction was a white mixture, and the solvent was removed under reduced pressure to produce a white matrix. The product was extracted with hexane (10 mL), the resulting white 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 light yellow liquid, and separated to obtain the product (1.44 g, 5.14 mmol), with a yield of 43.6%. The product was recorded on the concentrated C6D6 solution 1 H-, 13 C- and 119 Sn-NMR confirmed that the target molecule had been synthesized with >95% initial purity.

[0166] Figure 6 Shows the synthesis of EtSn(NMe2)3 from EtSnCl3(DME) recorded in C6D6 119 Sn-NMR. Long-term collection of more than 10,000 scans 119 Sn-NMR experiments were performed to confirm that Et2Sn(NMe2)2 (27.7 ppm) and Et3Sn(NMe2) (52.6 ppm) were not 119 Sn-NMR detected.

[0167] Example 5: Synthesis of Vinyl SnCl3(DME)

[0168] Figure 7 The solid-state 3D structure of vinyl SnCl3(DME) as determined by X-ray crystallography is shown. Table 2 shows the crystal data and structure refinement of vinyl SnCl3(DME).

[0169] Table 2: Crystallographic data and structure refinement of vinylSnCl3(DME).

[0170]

[0171]

[0172] In a nitrogen-filled glove box, dimethoxyethane (DME) (2.6 g, 28.8 mmol) was placed in a 40 mL vial, and vinyl SnCl (2.0 g, 7.93 mmol) was added dropwise, causing an immediate white precipitate and exotherm. X-ray quality crystals were grown by cooling a saturated DME solution of vinyl SnCl (DME) layered with hexane at -35 °C.

[0173] Figure 8 Shows the vinyl SnCl3 (DME) recorded in DME 119 Sn-NMR. 119 Sn{ 1H}-NMR (149 MHz, DME, 298K): -381.7 ppm (impurity from starting vinyl SnCl 3 at -291.6 ppm).

[0174] Example 6: Synthesis of Vinyl Sn(NMe2)3 Using DME / Hexane Containing Vinyl SnCl3(DME)

[0175] In a nitrogen-filled glove box, vinyl SnCl (15 g, 59.4 mmol) was added dropwise to dimethoxyethane (15 mL, 144 mmol) in a 250 mL flask equipped with a stirring bar. 50 mL of hexane was added to the flask and caused the vinyl SnCl adduct to crash out of the solution and mixture, becoming a suspension. Over 3.5 hours, LiNMe (9.38 g, 184 mmol) solid was added in small portions. The resulting white mixture was stirred overnight.

[0176] The volatiles were removed in vacuo. The residue was extracted with hexanes and filtered through a polypropylene (PP) sintered filter. The organic solution was dried under reduced pressure to give the product as a pale yellow liquid. 119 Sn-NMR recorded on a concentrated C6D6 solution of the product showed a.

[0177] Example 7: Synthesis of isopropenyl SnCl3 (DME)

[0178] Fig. 9 The solid-state 3D structure of isopropenyl SnCl3(DME) as determined by X-ray crystallography is shown. Table 3 shows the crystal data and structure refinement of isopropenyl SnCl3(DME).

[0179] Table 3: Crystallographic data and structure refinement of isopropenylSnCl3(DME).

[0180]

[0181] In nitrogen filled glove box, isopropenyl SnCl (2.0g, 7.51mmol) is placed in 40mL vial and diluted with hexane (7mL).Dimethoxyethane (1.73g, 19.1mmol) is added dropwise to isopropenyl SnCl solution, so as to produce white precipitate immediately.After adding DME completely, the vial is stirred at room temperature for 1 hour.Volatiles are removed by vacuum, and the white solid is washed with hexane.Then the remaining white solid is dried under reduced pressure.Quality: 2.63g, (97.7% yield).By cooling the isopropenyl SnCl of hexane layering at -35°C (DME) saturated DME solution to make X-ray quality crystal growth.

[0182] Fig.10Shows the isopropenyl SnCl3 (DME) recorded in C6D6 1 H-NMR. 1 H-NMR (400MHz, C6D6, 298K): 1.43 (s, 3H); 3.06 (s, 6H); 3.17 (s, 4H); 4.99 and 5.08 (s, 2H) ppm.

[0183] For the isopropenyl SnCl3 (DME) recorded in C6D6 13 C-NMR. 13 C{ 1 H}-NMR (100MHz, C6D6, 298K): 22.72; 58.73; 71.35; 131.34; 146.96ppm.

[0184] For the isopropenyl SnCl3 (DME) recorded in C6D6 119 Sn-NMR. 119 Sn{ 1 H}-NMR (149MHz, C6D6, 298K): -106.9ppm.

[0185] Example 8: Synthesis of isopropenyl Sn(NMe2)3 using THF / hexane containing isopropenyl SnCl3(DME)

[0186] In a nitrogen filled glove box, isopropenyl SnCl (2.0 g, 7.51 mmol) is added to dimethoxyethane (5 mL, 59.0 mmol), causing heat release and presenting as a white solid in the solution. Excess DME is removed in vacuo, and the solid is suspended in 10 mL hexane. Separately, LiNMe (1.14 g, 22.5 mmol) is placed in a 40 mL amber vial equipped with a magnetic stirring bar, and diluted with a 1: 1 solution (12 mL) of THF / hexane. Under stirring, the LiNMe mixture is added dropwise to the isopropenyl SnCl (DME) suspension, causing heat release and producing a white precipitate, and the resulting white mixture is stirred for 1 hour.

[0187] The reaction product appeared 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 with a yield of 63.9%. The product was recorded on the concentrated C6D6 solution. 1 H-, 13 C- and 119 Sn-NMR confirmed that the target molecule had been synthesized with >85% initial purity.

[0188] Fig.11The synthesis of isopropenyl Sn(NMe2)3 from isopropenyl SnCl3(DME) in THF / hexane solvent recorded in C6D6 is shown. 119 Sn-NMR.

[0189] Example 9: Synthesis of isopropenyl Sn(NMe2)3 using DME / hexane containing isopropenyl SnCl3(DME)

[0190] In a nitrogen-filled glove box, isopropenyl SnCl (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 stirring bar. Separately, LiNMe (1.13 g, 22.2 mmol) was suspended in a 1:1 solution (10 mL) of DME / hexane. The LiNMe mixture was added dropwise to the isopropenyl SnCl (DME) suspension under stirring, causing an exotherm and producing a white precipitate, and the resulting white mixture was stirred overnight.

[0191] The volatiles were removed in vacuo. The residue was extracted with hexane and filtered through a polypropylene (PP) sintered filter. The organic solution was dried under reduced pressure to give the product as a pale yellow liquid. 1.08 g (3.69 mmol) was isolated, 50.9% yield. The product was recorded on the concentrated C6D6 solution 1 H-, 13 C- and 119 Sn-NMR confirmed that the target molecule had been synthesized with >65% initial purity. Fig.12 Shows the synthesis of isopropenyl Sn(NMe2)3 from DME / hexane solvent containing isopropenyl SnCl3(DME) recorded in C6D6 119 Sn-NMR.

[0192] Example 10: Synthesis of isopropenyl Sn(NMe2)3 using hexane containing isopropenyl SnCl3(DME)

[0193] In a nitrogen-filled glove box, isopropenyl SnCl3 (2.6 g, 7.25 mmol) in hexane (5 mL) was added to a 40 mL amber vial with a stirring bar in which LiNMe2 (1.15 g, 22.7 mmol) was suspended in hexane (10 mL). An exotherm was observed and a white precipitate was produced, and the resulting mixture was stirred overnight.

[0194] The mixture was filtered through a polypropylene (PP) sintered filter. The solid was extracted with an additional 5 mL of hexane solvent. The organic solution was dried under reduced pressure to give the product as a pale yellow liquid. 1.97 g (6.74 mmol) was isolated, 89.9% yield. The product was recorded on the concentrated C6D6 solution1 H-, 13 C- and 119 Sn-NMR confirmed that the target molecule had been synthesized with >93% initial purity. Fig.13 The synthesis of isopropenyl Sn(NMe2)3 from hexane solvent containing isopropenyl SnCl3 recorded in C6D6 is shown. 119 Sn-NMR.

[0195] For the isopropenyl Sn(NMe2)3 recorded in C6D6 119 Sn-NMR. 119 Sn{ 1 H}-NMR (149MHz, C6D6, 298K): -87.4ppm (1.0%), -99.6ppm (93.1%), -119.0ppm (5.9%).

[0196] aspect

[0197] Various aspects are described below. It should be understood that any one or more features recited in the following aspects may be combined with any one or more other aspects.

[0198] Aspect 1. A method comprising: obtaining an alkyltin trihalide; obtaining a solvent, a solution, or any combination thereof; and contacting the alkyltin trihalide with the solvent, the solution, or any combination thereof to form an alkyltin trihalide adduct.

[0199] Aspect 2. The method according to aspect 1, wherein the method does not comprise forming an alkyltin trihalide-amine adduct.

[0200] Aspect 3. The method according to aspect 1 or 2, wherein the alkyltin trihalide-amine adduct is an alkyltin trihalide-(HNMe2) adduct.

[0201] Aspect 4. A method according to any one of the preceding aspects, wherein the alkyl tin trihalide is a compound of the following formula: RSnX3, wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; and X is Cl, Br or I.

[0202] Aspect 5. The method according to aspect 4, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2. In some aspects, the technology described herein relates to a method, wherein R is alkoxy.

[0203] Aspect 6. The method according to aspect 4, wherein R is vinyl, allyl, propynyl, propenyl or any isomer thereof.

[0204] Aspect 7. The method according to any one of the preceding aspects, wherein the solvent comprises at least one of the following: tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

[0205] Aspect 8. The method according to any one of aspects 1 to 6, wherein the solution comprises at least one of the following: hexane, pentane, toluene, or any combination thereof.

[0206] Aspect 9. A method according to any of the preceding aspects, wherein the solvent comprises at least one of the following: acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol, methyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, ethanol, ethyl acetate, ethylene glycol, glycerol, heptane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0207] Aspect 10. The method according to any one of the preceding aspects, wherein the trihalogenated alkyltin adduct is a compound of the formula: RSnX3·(solv) n , wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; X is Cl, Br, or I; solv is a solvent; and n is at least 1.

[0208] Aspect 11. A method comprising: obtaining an alkyltin trihalide adduct; obtaining a lithium dialkylamide; and contacting the alkyltin trihalide adduct with the lithium dialkylamide to form a tris(dialkylamido)alkyltin product.

[0209] Aspect 12. The method according to aspect 11, wherein the method does not comprise forming an alkyltin trihalide-amine adduct.

[0210] Aspect 13. The method according to aspect 12, wherein the alkyltin trihalide-amine adduct is an alkyltin trihalide-(HNMe2) adduct.

[0211] Aspect 14. The method according to any one of the preceding aspects, wherein the trihalogenated alkyltin adduct is a compound of the formula: RSnX3·(solv) n, wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; X is Cl, Br, or I; solv is a solvent; and n is at least 1.

[0212] Aspect 15. The method according to aspect 14, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2. In some aspects, the technology described herein relates to a method, wherein R is alkoxy.

[0213] Aspect 16. The method according to aspect 14, wherein R is vinyl, allyl, propynyl, propenyl or any isomer thereof.

[0214] Aspect 17. The method according to aspect 14, wherein the solvent comprises at least one of the following: acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, hexane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0215] Aspect 18. The method according to any one of the preceding aspects, wherein the lithium dialkylamide is a compound of the formula: LiN(R 1 )2, where: R 1 Contains C1-C3 alkyl.

[0216] Aspect 19. The method according to any one of the preceding aspects, wherein the tri(dialkylamido)alkyltin product is a compound of the formula:

[0217]

[0218] wherein R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; and wherein each R 1 are independently C1-C3 alkyl.

[0219] Aspect 20. A method comprising: obtaining an alkyltin trihalide; obtaining a solvent, a solution, or any combination thereof; and contacting the alkyltin trihalide with the solvent, the solution, or any combination thereof to form an alkyltin trihalide adduct; obtaining a lithium dialkylamide; and contacting the alkyltin trihalide adduct with the lithium dialkylamide to form a tris(dialkylamido)alkyltin product.

[0220] Aspect 21. The method according to aspect 20, wherein the method does not comprise forming an alkyltin trihalide-amine adduct.

[0221] Aspect 22. The method according to aspect 21, wherein the alkyltin trihalide-amine adduct is an alkyltin trihalide-(HNMe2) adduct.

[0222] Aspect 23. A method according to any one of the preceding aspects, wherein the alkyl tin trihalide is a compound of the formula: RSnX3, wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; and X is Cl, Br or I.

[0223] Aspect 24. The method according to aspect 23, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2. In some aspects, the technology described herein relates to a method, wherein R is alkoxy.

[0224] Aspect 25. The method according to aspect 23, wherein R is vinyl, allyl, propynyl, propenyl or any isomer thereof.

[0225] Aspect 26. The method according to any one of the preceding aspects, wherein the solvent comprises at least one of: tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof.

[0226] Aspect 27. The method according to any of the preceding aspects, wherein the solution comprises at least one of the following: hexane, pentane, toluene, or any combination thereof.

[0227] Aspect 28. A method according to any of the preceding aspects, wherein the solvent comprises at least one of the following: acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0228] Aspect 29. The method according to any one of the preceding aspects, wherein the trihalogenated alkyltin adduct is a compound of the formula: RSnX3·(solv) n , wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; X is Cl, Br, or I; solv is a solvent; and n is at least 1.

[0229] Aspect 30. The method according to any one of the preceding aspects, wherein the lithium dialkylamide is a compound of the formula: LiN(R 1 )2, where: R 1 Contains C1-C3 alkyl.

[0230] Aspect 31. The method according to any one of the preceding aspects, wherein the tri(dialkylamido)alkyltin product is a compound of the formula:

[0231]

[0232] wherein R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; wherein each R 1 are independently C1-C3 alkyl.

[0233] Aspect 32. A composition comprising: an alkyltin trihalide adduct of the formula: RSnX3·(solv) n , wherein: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; X is Cl, Br, or I; solv is a solvent; and n is at least 1.

[0234] Aspect 33. The composition according to aspect 32, wherein the solvent comprises at least one of the following: tetrahydrofuran (THF), dimethoxyethane (DME), hexane, or any combination thereof.

[0235] Aspect 34. The composition according to aspect 32, wherein the solvent comprises at least one of the following: acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, hexane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

[0236] Aspect 35. A composition comprising: a tri(dialkylamido)alkyltin product of the formula:

[0237]

[0238] wherein R is a substituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; wherein each R 1 are independently C1-C3 alkyl.

[0239] Aspect 36. The composition of aspect 35, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2, or CFH2. In some aspects, the technology described herein relates to a method, wherein R is alkoxy.

[0240] Aspect 37. The composition according to aspect 35, wherein R is vinyl, allyl, propynyl, propenyl or any isomer thereof.

[0241] Aspect 38. A composition comprising: a reaction product of an alkyltin trihalide adduct and a lithium dialkylamide, wherein the reaction product comprises a compound of the formula:

[0242]

[0243] wherein R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; wherein each R 1 are independently C1-C5 alkyl.

[0244] Aspect 39. A composition according to aspect 38, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2.

[0245] Aspect 40. The composition of aspect 38, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0246] Aspect 41. A composition comprising:

[0247] An atomic layer deposition precursor comprising an alkyltin trihalide of the formula:

[0248] RSnX3,

[0249] in:

[0250] R is a substituted C1-C5 alkyl group, an unsubstituted C1-C5 alkyl group, a substituted C1-C5 alkenyl group, or an unsubstituted C1-C5 alkenyl group; and

[0251] X is Cl, Br or I.

[0252] Aspect 42. A composition according to aspect 41, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2.

[0253] Aspect 43. The composition according to aspect 41, wherein R is vinyl, allyl, propynyl, propenyl or any isomer thereof.

[0254] Aspect 44. A composition comprising:

[0255] A chemical vapor deposition precursor comprising an alkyltin trihalide of the formula:

[0256] RSnX3,

[0257] in:

[0258] R is a substituted C1-C5 alkyl group, an unsubstituted C1-C5 alkyl group, a substituted C1-C5 alkenyl group, or an unsubstituted C1-C5 alkenyl group; and

[0259] X is Cl, Br or I.

[0260] Aspect 45. A composition according to aspect 44, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2.

[0261] Aspect 46. The composition of aspect 44, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

[0262] Aspect 47. A composition comprising:

[0263] The compound of the formula:

[0264]

[0265] in:

[0266] R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl;

[0267] R 2 are independently substituted C1-C4 alkyl or unsubstituted C1-C4 alkyl,

[0268] wherein the substituted C1-C4 alkyl group contains a fluorine-containing substituent.

[0269] Aspect 48. The composition according to aspect 47, wherein R 2 The C1-C4 alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

[0270] Aspect 49. The composition according to aspect 47, wherein the fluorine-containing substituent comprises -CH2CF3, -CH(CF3)2 or -(CH a ) n (CH b F c ) m ,

[0271] in:

[0272] a=0 to 3;

[0273] b = 0 to 2;

[0274] c = 1 to 3;

[0275] n = 0 to 3;

[0276] m=1 to 4.

[0277] Aspect 50. The composition according to aspect 49, wherein -(CH a ) n (CH b F c ) m It is -CH2F, -CH2CH2F, -CF3 or -CF2CF3.

[0278] Aspect 51. The composition according to aspect 47, wherein R 2 It is a saturated alkyl group or an unsaturated alkyl group.

[0279] Aspect 52. The composition according to aspect 47, wherein OR2 It is -OCH2C≡CH or -OCH=CH2.

[0280] Aspect 53. A composition comprising:

[0281] The compound of the formula:

[0282] RSn(OR 2 )3

[0283] in:

[0284] R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl;

[0285] R 2 are independently substituted C1-C4 alkyl or unsubstituted C1-C4 alkyl,

[0286] wherein the substituted C1-C4 alkyl group contains a fluorine-containing substituent.

[0287] Aspect 54. The composition according to aspect 53, wherein R 2 The C1-C4 alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

[0288] Aspect 55. The composition according to aspect 53, wherein the fluorine-containing substituent comprises -CH2CF3, -CH(CF3)2 or -(CH a ) n (CH b F c ) m ,

[0289] in:

[0290] a=0 to 3;

[0291] b = 0 to 2;

[0292] c = 1 to 3;

[0293] n = 0 to 3;

[0294] m=1 to 4.

[0295] Aspect 56. The composition according to aspect 55, wherein -(CH a ) n (CH b F c ) m It is -CH2F, -CH2CH2F, -CF3 or -CF2CF3.

[0296] Aspect 57. The composition according to aspect 53, wherein R 2 It is a saturated alkyl group or an unsaturated alkyl group.

[0297] Aspect 58. The composition according to aspect 53, wherein OR 2 It is -OCH2C≡CH or -OCH=CH2.

[0298] It should be understood that changes may be made in detail, especially in the construction materials employed, and the shape, size, and arrangement of parts without departing from the scope of the present disclosure. The specification and described embodiments are examples, with the true scope and spirit of the present disclosure being indicated by the appended claims.

Claims

1. A method comprising: Obtaining an alkyltin trihalide; obtaining a solvent, a solution, or any combination thereof; and The alkyltin trihalide is contacted with the solvent, the solution, or any combination thereof to form an alkyltin trihalide adduct.

2. The method of claim 1, wherein the method does not comprise forming an alkyltin trihalide-amine adduct.

3. The method according to claim 2, wherein the alkyltin trihalide-amine adduct is an alkyltin trihalide-(HNMe2) adduct.

4. The method according to claim 1, wherein the alkyltin trihalide is a compound of the formula: RSnX3, in: R is a substituted C1-C5 alkyl group, an unsubstituted C1-C5 alkyl group, a substituted C1-C5 alkenyl group, or an unsubstituted C1-C5 alkenyl group; and X is Cl, Br or I.

5. The method of claim 4, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2.

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

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

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

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

10. The method according to claim 1, wherein the alkyltin trihalide adduct is a compound of the formula: RSnX3·(silver) n , in: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; X is Cl, Br or I; solv is a solvent; and n is at least 1.

11. A method comprising: Obtaining an alkyltin trihalide adduct; Obtaining a lithium dialkylamide; and The alkyltin trihalide adduct is contacted with the lithium dialkylamide to form a tris(dialkylamido)alkyltin product.

12. The method of claim 11, wherein the method does not comprise forming an alkyltin trihalide-amine adduct.

13. The method according to claim 12, wherein the alkyltin trihalide-amine adduct is an alkyltin trihalide-(HNMe2) adduct.

14. The method according to claim 11, wherein the alkyltin trihalide adduct is a compound of the formula: RSnX3·(silver) n , in: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; X is Cl, Br or I; solv is a solvent; and n is at least 1.

15. The method of claim 14, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2.

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

17. The method of claim 14, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, hexane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

18. The method according to claim 11, wherein the dialkyl lithium amide is a compound of the formula: LiN(R 1 )2, in: R 1 Contains C1-C3 alkyl.

19. The method of claim 11, wherein the tri(dialkylamido)alkyltin product is a compound of the formula: wherein R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; and Among them, each R 1 are independently C1-C3 alkyl.

20. A method comprising: Obtaining an alkyltin trihalide; obtaining a solvent, a solution, or any combination thereof; and contacting the alkyltin trihalide with the solvent, the solution, or any combination thereof to form an alkyltin trihalide adduct; Obtaining a lithium dialkylamide; and The alkyltin trihalide adduct is contacted with the lithium dialkylamide to form a tris(dialkylamido)alkyltin product.

21. The method of claim 20, wherein the method does not comprise forming an alkyltin trihalide-amine adduct.

22. The method according to claim 21, wherein the alkyltin trihalide-amine adduct is an alkyltin trihalide-(HNMe2) adduct.

23. The method of claim 20, wherein the alkyltin trihalide is a compound of the formula: RSnX3, in: R is a substituted C1-C5 alkyl group, an unsubstituted C1-C5 alkyl group, a substituted C1-C5 alkenyl group, or an unsubstituted C1-C5 alkenyl group; and X is Cl, Br or I.

24. The method of claim 23, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2.

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

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

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

28. The method of claim 20, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

29. The method according to claim 20, wherein the alkyltin trihalide adduct is a compound of the formula: RSnX3·(silver) n , in: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; X is Cl, Br or I; solv is a solvent; and n is at least 1.

30. The method of claim 20, wherein the lithium dialkylamide is a compound of the formula: LiN(R 1 )2, in: R 1 Contains C1-C3 alkyl.

31. The method of claim 20, wherein the tris(dialkylamido)alkyltin product is a compound of the formula: wherein R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; Among them, each R 1 are independently C1-C3 alkyl.

32. A composition comprising: Alkyltin trihalide adducts of the formula: RSnX3·(silver) n , in: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; X is Cl, Br or I; solv is a solvent; and n is at least 1.

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

34. The composition of claim 32, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, tert-butanol, 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, glycerol, heptane, hexane, methanol, methyl tert-butyl ether, dichloromethane, N-methyl-2-pyrrolidone, pentane, petroleum ether, propanol, pyridine, tetrahydrofuran, toluene, triethylamine, water, xylene, any isomers thereof, or any combination thereof.

35. A composition comprising: The tri(dialkylamido)alkyltin product of the formula: wherein R is a substituted C1-C5 alkyl, a substituted C1-C5 alkenyl, or an unsubstituted C1-C5 alkenyl; Among them, each R 1 are independently C1-C3 alkyl.

36. The composition of claim 35, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2.

37. The composition of claim 35, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

38. A composition comprising: The reaction products of alkyltin trihalide adducts and lithium dialkylamides, wherein the reaction product comprises a compound of the formula: wherein R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; Among them, each R 1 are independently C1-C5 alkyl.

39. The composition of claim 38, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2 or CFH2.

40. The composition of claim 38, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

41. A composition comprising: An atomic layer deposition precursor comprising an alkyltin trihalide of the formula: RSnX3, in: R is a substituted C1-C5 alkyl group, an unsubstituted C1-C5 alkyl group, a substituted C1-C5 alkenyl group, or an unsubstituted C1-C5 alkenyl group; and X is Cl, Br or I.

42. The composition of claim 41, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2, or CFH2.

43. The composition of claim 41, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

44. A composition comprising: A chemical vapor deposition precursor comprising an alkyltin trihalide of the formula: RSnX3, in: R is a substituted C1-C5 alkyl group, an unsubstituted C1-C5 alkyl group, a substituted C1-C5 alkenyl group, or an unsubstituted C1-C5 alkenyl group; and X is Cl, Br or I.

45. The composition of claim 44, wherein R is methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, isopentyl, sec-pentyl, CF3CH2, CF2HCH2, CFH2CH2, or CFH2.

46. ​​The composition of claim 44, wherein R is vinyl, allyl, propynyl, propenyl, or any isomer thereof.

47. A composition comprising: The compound of the formula: in: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; R 2 are independently substituted C1-C4 alkyl or unsubstituted C1-C4 alkyl, wherein the substituted C1-C4 alkyl group contains a fluorine-containing substituent.

48. The composition according to claim 47, wherein R 2 The C1-C4 alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

49. The composition of claim 47, wherein the fluorine-containing substituent comprises -CH2CF3, -CH(CF3)2, or -(CH a ) n (CH b F c ) m , in: a=0 to 3; b = 0 to 2; c = 1 to 3; n = 0 to 3; m=1 to 4.

50. The composition according to claim 49, wherein -(CH a ) n (CH b F c ) m It is -CH2F, -CH2CH2F, -CF3 or -CF2CF3.

51. The composition according to claim 47, wherein R 2 It is a saturated alkyl group or an unsaturated alkyl group.

52. The composition of claim 47, wherein OR 2 It is -OCH2C≡CH or -OCH=CH2.

53. A composition comprising: The compound of the formula: RSn(OR 2 )3 in: R is a substituted C1-C5 alkyl, an unsubstituted C1-C5 alkyl, a substituted C1-C5 alkenyl or an unsubstituted C1-C5 alkenyl; R 2 are independently substituted C1-C4 alkyl or unsubstituted C1-C4 alkyl, wherein the substituted C1-C4 alkyl group contains a fluorine-containing substituent.

54. The composition according to claim 53, wherein R 2 The C1-C4 alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.

55. The composition of claim 53, wherein the fluorine-containing substituent comprises -CH2CF3, -CH(CF3)2 or -(CH a ) n (CH b F c ) m , in: a=0 to 3; b = 0 to 2; c = 1 to 3; n = 0 to 3; m=1 to 4.

56. The composition according to claim 55, wherein -(CH a ) n (CH b F c ) m It is -CH2F, -CH2CH2F, -CF3 or -CF2CF3.

57. The composition according to claim 53, wherein R 2 It is a saturated alkyl group or an unsaturated alkyl group.

58. The composition according to claim 53, wherein OR 2 It is -OCH2C≡CH or -OCH=CH2.

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