Functionalized organotin precursors and related methods

Abstract

Precursors useful for forming tin-containing films are provided. The precursors include functionalized tin compounds in which one or more ligands are coordinated to Sn and the Sn is functionalized with at least one functional group. Methods for forming the precursors and for forming tin-containing films using the precursors are also provided.

Description

[Technical Field]

[0001]

[0001] This disclosure relates to functionalized organotin precursors and related methods. [Background technology]

[0002]

[0002] Some precursors are useful in the fabrication of microelectronic devices, which may involve the use of extreme ultraviolet (EUV) lithography to form thin films. Summary of the Invention

[0003] Some embodiments relate to compositions. In some embodiments, the compositions comprise a compound of the following formula: Contains the precursor to TIFF2025537025000002.tif35170,

[0004] During the ceremony,

[0005] R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl;

[0006] L 1 , L 2 and L 3 are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate.

[0004]

[0007] In some embodiments, the precursor has a purity of at least 99%.

[0005]

[0008] In some embodiments, R is —CH 3 or —CH(CH 3 ) 2 .

[0006]

[0009] In some embodiments, R is —C 6 H 5 .

[0007]

[0010] In some embodiments, R is —CH 2 (C 6 H 5 ).

[0008]

[0011] In some embodiments, R is —CH 2 N(CH 3 ) 2 or —(CH 2 ) 3 N(CH 3 ) 2 .

[0009]

[0012] In some embodiments, R is —CH 2 CH 2 OCH 3 .

[0010]

[0013] In some embodiments, R is —CH 2 Si(CH 3 ) 3 .

[0011]

[0014] In some embodiments, R is —Si(CH 3 ) 3 .

[0012]

[0015] In some embodiments, L 1 , L 2 and L 3 are, independently, the following: At least one of TIFF2025537025000003.tif223170TIFF2025537025000004.tif148170,

[0016] During the ceremony,

[0017] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl.

[0013]

[0018] In some embodiments, L 1 , L 2 or L 3 is -N(CH3)2.

[0014]

[0019] In some embodiments, the precursor has the following chemical structure: I have TIFF2025537025000005.tif49170.

[0015]

[0020] In some embodiments, the precursor has the following chemical structure: I have TIFF2025537025000006.tif61170.

[0016]

[0021] Some embodiments relate to a method. In some embodiments, the method includes obtaining a tin compound. In some embodiments, the method includes obtaining a halogen compound. In some embodiments, the method includes contacting a tin compound with a halogen compound to obtain a compound of the formula: forming a precursor of TIFF2025537025000007.tif35170;

[0022] During the ceremony,

[0023] R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl;

[0024] L 1 , L 2 and L 3 are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate.

[0017]

[0025] In some embodiments, the tin compound comprises at least one compound of the formula: SnL2, wherein each L is independently selected from the group consisting of: L 1 , L 2 or L 3 where L 1 , L 2 or L 3 are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate.

[0018]

[0026] In some embodiments, L 1 , L 2 and L 3 are, independently, the following: At least one of TIFF2025537025000008.tif223170TIFF2025537025000009.tif148170,

[0027] During the ceremony,

[0028] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl.

[0019]

[0029] In some embodiments, the halogen compound has the formula: The compound is TIFF2025537025000010.tif7170.

[0030] During the ceremony,

[0031] R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl;

[0032] X is Cl, Br, F or I.

[0020]

[0033] In some embodiments, the tin compound and the halogen compound are contacted in a solvent.

[0021]

[0034] In some embodiments, the solvent comprises hexane.

[0022]

[0035] In some embodiments, the contacting is carried out under heating at a temperature in the range of 30°C to 150°C.

[0023]

[0036] Some embodiments relate to a method. In some embodiments, the method includes obtaining a precursor, the precursor having the formula: TIFF2025537025000011.tif35170,

[0037] During the ceremony,

[0038] R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl;

[0039] L 1 , L 2 and L 3 are each independently an amide, an alkoxide, an acetylide, a carbamate, or a carboxylate. In some embodiments, the method includes obtaining at least one co-reactant precursor. In some embodiments, the method includes vaporizing a precursor to obtain a vaporized precursor. In some embodiments, the method includes vaporizing at least one co-reactant precursor to obtain at least one vaporized co-reactant precursor. In some embodiments, the method includes contacting the at least one vaporized precursor, the at least one vaporized co-reactant precursor, or any combination thereof, with a substrate under vapor deposition conditions to form a tin-containing film on the substrate.

[0024]

[0040] In some embodiments, the precursor has a purity of at least 99%.

[0025]

[0041] In some embodiments, R is —CH 3 or —CH(CH 3 ) 2 .

[0026]

[0042] In some embodiments, R is —C 6 H 5 .

[0027]

[0043] In some embodiments, R is —CH 2 (C 6 H 5 ).

[0028]

[0044] In some embodiments, R is —CH 2 N(CH 3 ) 2 or —(CH 2 ) 3 N(CH 3 ) 2 .

[0029]

[0045] In some embodiments, R is —CH 2 CH 2 OCH 3 .

[0030]

[0046] In some embodiments, R is —CH 2 Si(CH 3 ) 3 .

[0031]

[0047] In some embodiments, R is —Si(CH 3 ) 3 .

[0032]

[0048] In some embodiments, L 1 , L 2 and L 3 are, independently, the following: At least one of TIFF2025537025000012.tif223170TIFF2025537025000013.tif148170,

[0049] During the ceremony,

[0050] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl.

[0033]

[0051] In some embodiments, L 1 , L 2 or L 3 is -N(CH3)2.

[0034]

[0052] In some embodiments, the precursor has the following chemical structure: I have TIFF2025537025000014.tif49170.

[0035]

[0053] In some embodiments, the precursor has the following chemical structure: I have TIFF2025537025000015.tif61170.

[0036]

[0054] Certain embodiments of the present disclosure are herein described, by way of example only, with reference to the accompanying drawings. Referring now in detail to the drawings, it is emphasized that the illustrated embodiments are exemplary and are intended for illustrative discussion of embodiments of the present disclosure. In this regard, when described in conjunction with the drawings, it will become apparent to those skilled in the art how embodiments of the present disclosure may be practiced. [Brief explanation of the drawings]

[0037] [Figure 1]

[0055] FIG. 1 is a flow diagram of a method for preparing a precursor, according to some embodiments. [Figure 2]

[0056] FIG. 1 is a flow diagram of a method for making a tin-containing film, according to some embodiments. DETAILED DESCRIPTION OF THE INVENTION

[0038]

[0057] Among the benefits and improvements disclosed, other objects and advantages of the present disclosure will become apparent from the following description taken in conjunction with the accompanying drawings. While detailed embodiments of the present disclosure are disclosed herein, it should be understood that the disclosed embodiments are merely exemplary of the present disclosure, which may be embodied in various forms. Moreover, the examples given of various embodiments of the present disclosure are intended to be illustrative rather than limiting.

[0039]

[0058] All prior patents and publications referenced herein are incorporated by reference in their entirety.

[0040]

[0059] Throughout this specification and claims, the following terms have the meanings expressly associated therewith unless the context clearly dictates otherwise. As used herein, the phrases "in one embodiment," "in an embodiment," and "in some embodiments" do not necessarily refer to the same embodiment, although they may. Additionally, as used herein, the phrases "in another embodiment" and "in some other embodiments" do not necessarily refer to different embodiments, although they may. It is intended that all embodiments of the present disclosure be combinable without departing from the scope or spirit of the disclosure.

[0041]

[0060] As used herein, the term "based on" is not exclusive and allows for the use of additional unrecited factors unless the context clearly indicates otherwise. Additionally, throughout this specification, the meanings of "a," "an," and "the" include plural references. The meaning of "in" includes "in" and "on."

[0042]

[0061] As used herein, the term "alkyl" refers to a hydrocarbyl having 1 to 30 carbon atoms. The alkyl may be attached via a single bond. An alkyl having n carbon atoms is referred to as "C n For example, "C alkyl" can include n-propyl and isopropyl. Alkyl having a range of carbon atoms, such as 1 to 30 carbon atoms, can be specified as C1-C 30 In some embodiments, alkyl may be specified as alkyl. In some embodiments, alkyl is linear. In some embodiments, alkyl is branched. In some embodiments, alkyl is substituted. In some embodiments, alkyl is unsubstituted. In some embodiments, alkyl is C-C 30 Alkyl, C1-C 29 Alkyl, C1-C 28 Alkyl, C1-C 27 Alkyl, C1-C 27 Alkyl, C1-C 26 Alkyl, C1-C25 Alkyl, C1-C 24 Alkyl, C1-C 23 Alkyl, C1-C 22 Alkyl, C1-C 21 Alkyl, C1-C 20 Alkyl, C1-C 19 Alkyl, C1-C 18 Alkyl, C1-C 17 Alkyl, C1-C 16 Alkyl, C1-C 15 Alkyl, C1-C 14 Alkyl, C1-C 13 Alkyl, C1-C 12 Alkyl, C1-C 11 Alkyl, C1-C 10 Alkyl, C1-C9 alkyl, C1-C8 alkyl, C1-C7 alkyl, C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl, C1-C2 alkyl, C2-C 30 Alkyl, C3-C 30 Alkyl, C4-C 30 Alkyl, C5-C 30 Alkyl, C6-C 30 Alkyl, C7-C 30 Alkyl, C8-C 30 Alkyl, C9-C 30 Alkyl, C 10 -C 30 Alkyl, C 11 -C 30 Alkyl, C 12 -C 30 Alkyl, C 13 -C 30 Alkyl, C 14 -C 30 Alkyl, C 15 -C 30 Alkyl, C 16 -C 30 Alkyl, C 17 -C 30 Alkyl, C 18 -C 30 Alkyl, C 19 -C 30 Alkyl, C 20 -C 30 Alkyl, C 21 -C30 Alkyl, C 22 -C 30 Alkyl, C 23 -C 30 Alkyl, C 24 -C 30 Alkyl, C 25 -C 30 Alkyl, C 26 -C 30 Alkyl, C 27 -C 30 Alkyl, C 28 -C 30 Alkyl, C 29 -C 30 Alkyl, C2-C 10 Alkyl, C3-C 10 Alkyl, C4-C 10 Alkyl, C5-C 10 Alkyl, C6-C 10 Alkyl, C7-C 10 Alkyl, C8-C 10

[0023] The term "alkyl" may be selected from the group consisting of at least one of alkyl, C2-C9 alkyl, C2-C8 alkyl, C2-C7 alkyl, C2-C6 alkyl, C2-C5 alkyl, C3-C5 alkyl, or any combination thereof. In some embodiments, the alkyl may be selected from the group consisting of at least one of methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, iso-butyl, sec-butyl, n-pentyl, 1,1-dimethylethyl (t-butyl), n-pentyl, isopentyl, n-hexyl, isohexyl, 3-methylhexyl, 2-methylhexyl, heptyl, octyl, nonyl, decyl, dodecyl, octadecyl, or any combination thereof. In some embodiments, the term "alkyl" refers generally to alkyl, alkenyl, alkynyl, and / or cycloalkyl.

[0043]

[0062] As used herein, the term "alkenyl" refers to a hydrocarbyl having 1 to 30 carbon atoms and at least one carbon-carbon double bond. In some embodiments, alkenyl is a C-C 30 Alkenyl, C1-C29 Alkenyl, C1-C 28 Alkenyl, C1-C 27 Alkenyl, C1-C 27 Alkenyl, C1-C 26 Alkenyl, C1-C 25 Alkenyl, C1-C 24 Alkenyl, C1-C 23 Alkenyl, C1-C 22 Alkenyl, C1-C 21 Alkenyl, C1-C 20 Alkenyl, C1-C 19 Alkenyl, C1-C 18 Alkenyl, C1-C 17 Alkenyl, C1-C 16 Alkenyl, C1-C 15 Alkenyl, C1-C 14 Alkenyl, C1-C 13 Alkenyl, C1-C 12 Alkenyl, C1-C 11 Alkenyl, C1-C 10 Alkenyl, C1-C 9ア alkenyl, C1-C8 alkenyl, C1-C7 alkenyl, C1-C6 alkenyl, C1-C5 alkenyl, C1-C4 alkenyl, C1-C3 alkenyl, C1-C2 alkenyl, C2-C 30 Alkenyl, C3-C 30 Alkenyl, C4-C 30 Alkenyl, C5-C 30 Alkenyl, C6-C 30 Alkenyl, C7-C 30 Alkenyl, C8-C 30 Alkenyl, C9-C 30 Alkenyl, C 10 -C 30 Alkenyl, C 11 -C 30 Alkenyl, C 12 -C 30 Alkenyl, C 13 -C 30 Alkenyl, C 14 -C 30 Alkenyl, C 15 -C 30 Alkenyl, C 16 -C 30Alkenyl, C 17 -C 30 Alkenyl, C 18 -C 30 Alkenyl, C 19 -C 30 Alkenyl, C 20 -C 30 Alkenyl, C 21 -C 30 Alkenyl, C 22 -C 30 Alkenyl, C 23 -C 30 Alkenyl, C 24 -C 30 Alkenyl, C 25 -C 30 Alkenyl, C 26 -C 30 Alkenyl, C 27 -C 30 Alkenyl, C 28 -C 30 Alkenyl, C 29 -C 30 Alkenyl, C2-C 10 Alkenyl, C3-C 10 Alkenyl, C4-C 10 Alkenyl, C5-C 10 Alkenyl, C6-C 10 Alkenyl, C7-C 10 Alkenyl, C8-C 10The alkenyl group may include, but is not limited to, at least one of alkenyl, C2-C9 alkenyl, C2-C8 alkenyl, C2-C7 alkenyl, C2-C6 alkenyl, C2-C5 alkenyl, C3-C5 alkenyl, or any combination thereof. Examples of alkenyl groups include, but are not limited to, vinyl, allyl, 1-methylvinyl, 1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 2,4-pentadienyl, 1,4-pentadienyl, 3-methyl-2-butenyl, At least one of 1-hexenyl, 2-hexenyl, 3-hexenyl, 1,3-hexadienyl, 1,4-hexadienyl, 2-methylpentenyl, 1-heptenyl, 3-heptenyl, 1-octenyl, 1,3-octadienyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 1-decenyl, 3-decenyl, 1-undecenyl, oleyl, linoleyl, linolenyl, or any combination thereof.

[0044]

[0063] As used herein, the term "alkynyl" refers to a hydrocarbyl having 1 to 30 carbon atoms and at least one carbon-carbon triple bond. In some embodiments, alkynyl is a C1-C 30 Alkynyl, C1-C 29 Alkynyl, C1-C 28 Alkynyl, C1-C 27 Alkynyl, C1-C 27 Alkynyl, C1-C 26 Alkynyl, C1-C 25 Alkynyl, C1-C 24 Alkynyl, C1-C 23 Alkynyl, C1-C 22 Alkynyl, C1-C 21 Alkynyl, C1-C 20 Alkynyl, C1-C 19 Alkynyl, C1-C 18 Alkynyl, C1-C 17 Alkynyl, C1-C 16Alkynyl, C1-C 15 Alkynyl, C1-C 14 Alkynyl, C1-C 13 Alkynyl, C1-C 12 Alkynyl, C1-C 11 Alkynyl, C1-C 10 Alkynyl, C1-C9 alkynyl, C1-C8 alkynyl, C1-C7 alkynyl, C1-C6 alkynyl, C1-C5 alkynyl, C1-C4 alkynyl, C1-C3 alkynyl, C1-C2 alkynyl, C2-C 30 Alkynyl, C3-C 30 Alkynyl, C4-C 30 Alkynyl, C5-C 30 Alkynyl, C6-C 30 Alkynyl, C7-C 30 Alkynyl, C8-C 30 Alkynyl, C9-C 30 Alkynyl, C 10 -C 30 Alkynyl, C 11 -C 30 Alkynyl, C 12 -C 30 Alkynyl, C 13 -C 30 Alkynyl, C 14 -C 30 Alkynyl, C 15 -C 30 Alkynyl, C 16 -C 30 Alkynyl, C 17 -C 30 Alkynyl, C 18 -C 30 Alkynyl, C 19 -C 30 Alkynyl, C 20 -C 30 Alkynyl, C 21 -C 30 Alkynyl, C 22 -C 30 Alkynyl, C 23 -C 30 Alkynyl, C 24 -C 30 Alkynyl, C 25 -C 30 Alkynyl, C 26 -C30 Alkynyl, C 27 -C 30 Alkynyl, C 28 -C 30 Alkynyl, C 29 -C 30 Alkynyl, C2-C 10 Alkynyl, C3-C 10 Alkynyl, C4-C 10 Alkynyl, C5-C 10 Alkynyl, C6-C 10 Alkynyl, C7-C 10 Alkynyl, C8-C 10 and n-, n-hexynyl, methyl-pent ...

[0045]

[0064] As used herein, the term "cycloalkyl" refers to a non-aromatic carbocyclic ring having 3 to 8 carbon atoms within the ring. This term includes monocyclic non-aromatic carbocyclic rings and polycyclic non-aromatic carbocyclic rings. The term "monocyclic," when used as a modifier, refers to a cycloalkyl having a single cyclic ring structure. The term "polycyclic," when used as a modifier, refers to a cycloalkyl having two or more cyclic ring structures, which may be fused, bridged, spiro, or otherwise linked ring structures. For example, two or more cycloalkyls may be fused, bridged, or fused and bridged to give a polycyclic non-aromatic carbocyclic ring. In some embodiments, a cycloalkyl may comprise, consist of, consist essentially of, or be selected from the group consisting of at least one of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, or any combination thereof.

[0046]

[0065] As used herein, the term "aryl" refers to a monocyclic or polycyclic aromatic hydrocarbon. The number of carbon atoms in an aryl can range from 5 carbon atoms to 100 carbon atoms. In some embodiments, an aryl has 5 to 20 carbon atoms. For example, in some embodiments, an aryl has 6 to 8 carbon atoms, 6 to 10 carbon atoms, 6 to 12 carbon atoms, 6 to 15 carbon atoms, or 6 to 20 carbon atoms. The term "monocyclic," when used as a modifier, refers to an aryl having a single aromatic ring structure. The term "polycyclic," when used as a modifier, refers to an aryl having two or more aromatic ring structures, which may be fused, bridged, spiro, or otherwise linked ring structures. In some embodiments, an aryl is -CH.

[0047]

[0066] As used herein, the term "alkoxy" refers to a group of the formula -OR a In the formula, R a is alkyl, as defined herein. In some embodiments, alkoxy can comprise, consist essentially of, or be selected from the group consisting of at least one of methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, or any combination thereof.

[0048]

[0067] As used herein, the terms “amine” and “amino” refer to a group of the formula —N(R b R c R d ) functional group, in which R b , R c and R dis independently hydrogen or alkyl, as defined herein. In some embodiments, the amine can comprise, consist of, or consist essentially of a primary amine, a secondary amine, a tertiary amine, or a quaternary amine. In some embodiments, the amine can comprise, consist of, or consist essentially of an alkyl amine, a dialkyl amine, or a trialkyl amine. In some embodiments, the amine can comprise, consist of, or consist of, or be selected from the group consisting of, methylamine, dimethylamine, ethylamine, diethylamine, isopropylamine, di-isopropylamine, butylamine, sec-butylamine, tert-butylamine, di-sec-butylamine, isobutylamine, di-isobutylamine, di-tert-pentylamine, ethylmethylamine, isopropyl-n-propylamine, or any combination thereof.Examples of alkylamines include, but are not limited to, primary alkylamines, such as, but not limited to, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, sec-butylamine, isobutylamine, t-butylamine, pentylamine, 2-aminopentane, 3-aminopentane, 1-amino-2-methylbutane, 2-amino-2-methylbutane, 3-amino-2-methylbutane, 4-amino-2-methylbutane, hexylamine, 5-amino-2-methylpentane, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, and octadecylamine; and secondary alkylamines, such as, but not limited to, may include one or more of dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diisobutylamine, di-sec-butylamine, di-t-butylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, methylethylamine, methylpropylamine, methylisopropylamine, methylbutylamine, methylisobutylamine, methyl-sec-butylamine, methyl-t-butylamine, methylamylamine, methylisoamylamine, ethylpropylamine, ethylisopropylamine, ethylbutylamine, ethylisobutylamine, ethyl-sec-butylamine, ethylamine, ethylisoamylamine, propylbutylamine, and propylisobutylamine. In some embodiments, the amine is —N(CH3)2.

[0049]

[0068] As used herein, the term "silyl" refers to a group of the formula -Si(R e R f R g ) functional group, in which R e , R f and R gEach of is independently hydrogen or alkyl, as defined herein. In some embodiments, the silyl is a functional group of formula -SiH. In some embodiments, the silyl is a functional group of formula -SiR e H2 functional group, where R e is not hydrogen. In some embodiments, silyl is of the formula -SiR e R f H functional group, where R e and R f is not hydrogen. In some embodiments, silyl is represented by the formula -Si(R e R f R g ) functional group, wherein R e , R f and R g is not hydrogen. In some embodiments, the silyl is a functional group of formula -Si(CH3)3.

[0050]

[0069] As used herein, the term "alkoxyalkyl" refers to an alkyl, as defined herein, in which at least one of the alkyl's hydrogen atoms has been replaced with an alkoxy, as defined herein. In some embodiments, the term "alkoxyalkyl" refers to a group of the formula -(alkyl)OR a where alkyl is defined above and R a is defined above. In some embodiments, alkoxyalkyl is of the formula -(CH) n OR a where n is 1 to 10, and R a is defined above. In some embodiments, the alkoxyalkyl is a functional group of formula -CH2CH2OCH3.

[0051]

[0070] As used herein, the term "aralkyl" refers to an alkyl, as defined herein, in which at least one of the hydrogen atoms of the alkyl is replaced with an aryl, as defined herein. In some embodiments, the term "aralkyl" refers to a functional group of formula -(alkyl)(aryl), where alkyl is defined herein and aryl is defined herein. In some embodiments, the aralkyl is -CH(CH).

[0052]

[0071] As used herein, the term "aminoalkyl" refers to an alkyl, as defined herein, in which at least one of the hydrogen atoms of the alkyl has been replaced with an amino, as defined herein. In some embodiments, the term "aminoalkyl" refers to a group of the formula -(alkyl)N(R b R c R d ), where alkyl is defined above and R b , R c and R d is defined above. In some embodiments, the aminoalkyl is -CHN(CH). In some embodiments, the aminoalkyl is -(CH)N(CH). In some embodiments, the aminoalkyl is aminomethyl (-CHNH). In some embodiments, the aminoalkyl is N,N-dimethylaminoethyl (-CHCHN(CH)). In some embodiments, the aminoalkyl is 3-(N-cyclopropylamino)propyl (-CHCHCHNH-Pr).

[0053]

[0072] As used herein, the term "silylalkyl" refers to an alkyl, as defined herein, in which at least one of the hydrogen atoms of the alkyl has been replaced with a silyl, as defined herein. In some embodiments, the term "silylalkyl" refers to a group of the formula -(alkyl)Si(R e R f R g ), where alkyl is defined above and R e, R f and R g is defined above. In some embodiments, the silylalkyl has the formula -(CH) m Si(R e R f R g ) functional group, wherein m is 1 to 10, and R e , R f and R g is defined above. In some embodiments, the silylalkyl is a functional group of formula -CH2Si(CH3)3.

[0054]

[0073] As used herein, the term "halide" refers to -Cl, -Br, -I, or -F.

[0055]

[0074] Some embodiments relate to precursor compositions and related methods. The precursor compositions disclosed herein include, among other things, alkyl-substituted precursors and silyl-substituted precursors. The precursor compositions can be used to form tin-containing films useful in the fabrication of microelectronic devices, including semiconductor devices. For example, the precursor compositions can be used to form functionalized tin oxide films (RSnO x The functionalized tin oxide films can be used, among other things, as reflective coatings for dry resist applications and extreme ultraviolet (EUV) lithography. According to the methods disclosed herein, the precursor compositions can be formed in high yield and purity while minimizing the number of steps required to manufacture the precursor compositions.

[0056]

[0075] Tin-containing films can also be formed according to the methods disclosed herein. That is, the tin-containing films disclosed herein can be formed by one or more deposition processes utilizing precursor compositions. Examples of deposition processes include, but are not limited to, at least one of a chemical vapor deposition (CVD) process, a digital or pulsed chemical vapor deposition process, a plasma-enhanced cyclic chemical vapor deposition process (PECCVD), a flowable chemical vapor deposition process (FCVD), an atomic layer deposition (ALD) process, a thermal atomic layer deposition, a plasma-enhanced atomic layer deposition (PEALD) process, a metal-organic chemical vapor deposition (MOCVD) process, a plasma-enhanced chemical vapor deposition (PECVD) process, or any combination thereof.

[0057]

[0076] The precursor composition may include a precursor. In some embodiments, the precursor is a functionalized tin compound in which one or more ligands are coordinated to tin (Sn). In some embodiments, the tin compound is functionalized with an alkyl group, which may be saturated or unsaturated, cyclic or acyclic, substituted or unsubstituted. In some embodiments, the tin compound is functionalized with a silyl group. The functional group may include one or more substituents. In some embodiments, the substituents include at least one of nitrogen, silicon, oxygen, chlorine, bromine, fluorine, iodine, nitrile, imine, carbonyl, or any combination thereof.

[0058]

[0077] In some embodiments, the precursor composition has the following formula: Contains the precursor to TIFF2025537025000016.tif35170,

[0078] During the ceremony,

[0079] R is a functional group;

[0080] L 1 , L 2 and L 3 is a ligand coordinated to Sn.

[0059]

[0081] In some embodiments, R is hydrocarbyl. In some embodiments, R is hydrosilyl. In some embodiments, R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, or any combination thereof. In some embodiments, R is alkyl. In some embodiments, R is alkenyl. In some embodiments, R is alkynyl. In some embodiments, R is cycloalkyl. In some embodiments, R is aryl. In some embodiments, R is silyl. In some embodiments, R is silylalkyl. In some embodiments, R is aminoalkyl. In some embodiments, R is alkoxyalkyl. In some embodiments, R is aralkyl. In some embodiments, R comprises a halide. In some embodiments, R comprises at least one of nitrile, imine, carbonyl, nitrogen, silicon, oxygen, chlorine, bromine, fluorine, element, or any combination thereof.

[0060]

[0082] In some embodiments, L 1 , L 2 and L 3 are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate. 1 , L 2 and L 3 are each independently an amine, an alkoxy, an alkenyl, an alkynyl, a carbamate, or a carboxyl. 1 , L 2 and L 3 are, independently, the following: At least one of TIFF2025537025000017.tif223170TIFF2025537025000018.tif148170,

[0083] During the ceremony,

[0084] R 1 , R 2, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl.

[0061]

[0085] In some embodiments, the precursor composition has the following formula: Contains precursor to TIFF2025537025000019.tif49170.

[0062]

[0086] In some embodiments, the precursor composition has the following formula: Contains precursor to TIFF2025537025000020.tif61170.

[0063]

[0087] 1 is a flow diagram of a method 100 for preparing a precursor, according to some embodiments. As shown in FIG. 1, the method 100 for preparing a precursor can include one or more of the following steps: obtaining a tin compound in step 102; obtaining a halogen compound in step 104; and contacting the tin compound with the halogen compound to form a precursor in step 106. In some embodiments, the precursor has the formula: TIFF2025537025000021.tif35170,

[0088] During the ceremony,

[0089] R is a functional group;

[0090] L 1 , L 2 and L 3 is a ligand coordinated to Sn.

[0064]

[0091] In some embodiments, the tin compound comprises at least one compound of the formula: SnL2, wherein each L is independently selected from the group consisting of: L 1 , L 2 or L 3is.

[0065]

[0092] In some embodiments, L 1 , L 2 and L 3 is each independently at least one of an amide, an alkoxide, an acetylide, a carbamate, a carboxylate, or any combination thereof. 1 , L 2 and L 3 is each independently at least one of an amine, an alkoxy, an alkenyl, an alkynyl, a carbamate, a carboxyl, or any combination thereof. 1 , L 2 and L 3 are, independently, the following: At least one of TIFF2025537025000022.tif223170TIFF2025537025000023.tif148170,

[0093] During the ceremony,

[0094] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl.

[0066]

[0095] In some embodiments, the halogen compound has the formula: The compound is TIFF2025537025000024.tif7170.

[0096] During the ceremony,

[0097] R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl;

[0098] X is Cl, Br, F or I.

[0067]

[0099] In some embodiments, the contacting comprises direct contacting or immediate proximity or close proximity. In some embodiments, the contacting comprises combining or adding to a reaction flask, reaction vial, or reactor. In some embodiments, the contacting comprises at least one of diluting the tin compound, diluting the halogen compound, dissolving the tin compound, dissolving the halogen compound, stirring the tin compound, stirring the halogen compound, or any combination thereof. In some embodiments, the contacting comprises adding the halogen compound to the tin compound dropwise. In some embodiments, the contacting comprises adding the tin compound to the halogen compound dropwise. In some embodiments, the contacting is performed under heating.

[0068]

[0100] In some embodiments, the contacting is carried out under heating at or to a temperature in the range of 30° C. to 150° C. In some embodiments, the heating is carried out at or to a temperature in the range of 30° C. to 140° C., 30° C. to 130° C., 30° C. to 120° C., 30° C. to 110° C., 30° C. to 100° C., 30° C. to 90° C., 30° C. to 80° C., 30° C. to 70° C., 30° C. to 60° C., 30° C. to 50° C., 30° C. to 40° C., 40° C. to 150° C., 50° C. to 150° C., 60° C. to 150° C., 70° C. to 150° C., 80° C. to 150° C., 90° C. to 150° C., 100° C. to 150° C., 110° C. to 150° C., 120° C. to 150° C., 130° C. to 150° C., or 140° C. to 150° C.

[0069]

[0101] In some embodiments, the contacting is carried out in a solvent. In some embodiments, the solvent comprises hexane.

[0070]

[0102] In some embodiments, the precursor is selected from the group consisting of aryl, ... Formed according to TIFF2025537025000025.tif20170,

[0103] During the ceremony,

[0104] R is defined above;

[0105] X is defined above;

[0106] Each L is independently 1 , L 2 or L 3 is.

[0071]

[0107] 2 is a flow diagram of a method for making a tin-containing film 200, according to some embodiments. As shown in FIG. 2, the method for making the tin-containing film 200 may include, consist of, or consist essentially of one or more of the following steps: obtaining a precursor 202, obtaining at least one co-reactant precursor 204, vaporizing the precursor to obtain a vaporized precursor 206, vaporizing the at least one co-reactant precursor to obtain at least one vaporized co-reactant precursor 208, and contacting at least one of the vaporized precursor, the at least one vaporized co-reactant precursor, or any combination thereof, with a substrate under vapor deposition conditions 210 to form a tin-containing film on the substrate.

[0072]

[0108] Step 202 can include, consist of, or consist essentially of obtaining a precursor. The precursor can include, consist of, or consist essentially of any one or more of the precursors disclosed herein. Obtaining can include obtaining a vessel or other container containing the precursor. In some embodiments, the precursor can be obtained in a vessel or other container from which the precursor is vaporized.

[0073]

[0109] Step 204 may include, consist of, or consist essentially of obtaining at least one co-reactant precursor. In some embodiments, the at least one co-reactant precursor comprises, consists of, consists essentially of, or is selected from the group consisting of at least one of an oxidizing gas, a reducing gas, a hydrocarbon, or any combination thereof. The at least one co-reactant precursor may be selected to obtain a desired tin-containing film. In some embodiments, the at least one co-reactant precursor may comprise, consist of, or consist essentially of at least one of N2, H2, NH3, N2H4, CH3HNNH2, CH3HNNHCH3, NCH3H2, NCH3CH2H2, N(CH3)2H, N(CH3CH2)2H, N(CH3)3, N(CH3CH2)3, Si(CH3)2NH, pyrazoline, pyridine, ethylenediamine, or any combination thereof. In some embodiments, the at least one co-reactant precursor may comprise, consist of, or consist essentially of at least one of H, O, O, HO, HO, NO, NO, NO, CO, CO, a carboxylic acid, an alcohol, a diol, or any combination thereof. In some embodiments, the at least one co-reactant precursor comprises, consists of, or consists essentially of at least one of methane, ethane, ethylene, acetylene, or any combination thereof. Obtaining may include obtaining a vessel or other container containing the at least one co-reactant precursor. In some embodiments, the at least one co-reactant precursor may be obtained in a vessel or other container from which the at least one co-reactant precursor is vaporized. In some embodiments, the method further includes an inert gas, such as, for example, at least one of argon, helium, nitrogen, or any combination thereof.

[0074]

[0110] Step 206 may include, consist of, or consist essentially of vaporizing the precursor to obtain a vaporized precursor. Vaporizing may include, consist of, or consist essentially of heating the precursor sufficiently to obtain a vaporized precursor. In some embodiments, vaporizing may include, consist of, or consist essentially of heating a container containing the precursor. In some embodiments, vaporizing may include, consist of, or consist essentially of heating the precursor in a deposition chamber in which the vapor deposition process is performed. In some embodiments, vaporizing may include, consist of, or consist essentially of heating a conduit for delivering the precursor, vaporized precursor, or any combination thereof, for example, to the deposition chamber. In some embodiments, vaporizing may include, consist of, or consist essentially of operating a vapor delivery system containing the precursor. In some embodiments, vaporizing may include, consist of, or consist essentially of heating the precursor to a temperature sufficient to vaporize it to obtain the vaporized precursor. In some embodiments, vaporizing may include, consist of, or consist essentially of heating to a temperature below the decomposition temperature of at least one of the precursor, the vaporized precursor, or any combination thereof. In some embodiments, the precursor may be in the gas phase, in which case step 206 is optional and not required. For example, the precursor may include, consist of, or consist essentially of the vaporized precursor.

[0075]

[0111] Step 208 may include, consist of, or consist essentially of vaporizing at least one co-reactant precursor to obtain at least one vaporized co-reactant precursor. In some embodiments, vaporizing may include, consist of, or consist essentially of heating the at least one co-reactant precursor sufficient to obtain at least one vaporized co-reactant precursor. In some embodiments, vaporizing may include, consist of, or consist essentially of heating a container containing the at least one co-reactant precursor. In some embodiments, vaporizing may include, consist of, or consist essentially of heating the at least one co-reactant precursor in a deposition chamber in which the vapor deposition process is performed. In some embodiments, vaporizing may include, consist of, or consist essentially of heating a conduit for delivering the at least one co-reactant precursor, the at least one vaporized co-reactant precursor, or any combination thereof, e.g., to the deposition chamber. In some embodiments, vaporizing may include, consist of, or consist essentially of operating a vapor delivery system containing at least one co-reactant precursor. In some embodiments, vaporizing may include, consist of, or consist essentially of heating at least one co-reactant precursor to a temperature sufficient to vaporize it to obtain at least one vaporized co-reactant precursor. In some embodiments, vaporizing may include, consist of, or consist essentially of heating to a temperature below the decomposition temperature of at least one of the at least one co-reactant precursor, the at least one vaporized co-reactant precursor, or any combination thereof. In some embodiments, at least one co-reactant precursor may be in the vapor phase, in which case step 108 is optional and not required. For example, at least one co-reactant precursor may include, consist of, or consist essentially of at least one vaporized co-reactant precursor.

[0076]

[0112] Step 210 may include, consist of, or consist essentially of contacting at least one of the vaporized precursor, at least one vaporized co-reactant precursor, or any combination thereof, with a substrate under vapor deposition conditions sufficient to form a tin-containing film on the surface of the substrate. The contacting may occur in any system, apparatus, device, assembly, chamber, or component thereof suitable for a vapor deposition process, including, but not limited to, a deposition chamber. The vaporized precursor and at least one co-reactant precursor may be contacted with the substrate simultaneously or at different times. For example, the vaporized precursor, the at least one vaporized co-reactant precursor, and the substrate may each be present in the deposition chamber at the same time. That is, in some embodiments, the contacting may include contemporaneous or simultaneous contacting of the vaporized precursor and at least one vaporized co-reactant precursor with the substrate. Alternatively, the vaporized precursor and at least one vaporized co-reactant precursor may each be present in the deposition chamber at different times. That is, in some embodiments, the contacting may involve alternating and / or sequential contacting of a vaporized precursor with the substrate followed by contacting at least one vaporized co-reactant precursor with the substrate in one or more cycles.

[0077]

[0113] The vapor deposition conditions may include conditions for a vapor deposition process. Examples of vapor deposition conditions include, but are not limited to, vapor deposition conditions for a vapor deposition process including at least one of a chemical vapor deposition (CVD) process, a digital or pulsed chemical vapor deposition process, a plasma-enhanced cyclic chemical vapor deposition process (PECCVD), a flowable chemical vapor deposition process (FCVD), an atomic layer deposition (ALD) process, a thermal atomic layer deposition, a plasma-enhanced atomic layer deposition (PEALD) process, a metal-organic chemical vapor deposition (MOCVD) process, a plasma-enhanced chemical vapor deposition (PECVD) process, or any combination thereof.

[0078]

[0114] The vapor deposition conditions can include, consist of, or consist essentially of a deposition temperature. The deposition temperature can be a temperature below the thermal decomposition temperature of at least one of the vaporized precursor, at least one vaporized co-reactant precursor, or any combination thereof. The deposition temperature can be sufficiently high to reduce or avoid condensation of at least one of the vaporized precursor, at least one vaporized co-reactant precursor, or any combination thereof. In some embodiments, the substrate can be heated to the deposition temperature. In some embodiments, the chamber or other container in which the substrate is contacted with the vaporized precursor and at least one vaporized co-reactant precursor is heated to the deposition temperature. In some embodiments, at least one of the vaporized precursor, at least one vaporized co-reactant precursor, or any combination thereof can be heated to the deposition temperature.

[0079]

[0115] The deposition temperature can be between 200° C. and 2500° C. In some embodiments, the deposition temperature can be between 500° C. and 700° C. For example, in some embodiments, the deposition temperature can be between 500° C. and 680° C., 500° C. and 660° C., 500° C. and 640° C., 500° C. and 620° C., 500° C. and 600° C., 500° C. and 580° C., 500° C. and 560° C., 500° C. and 540° C., 500° C. and 520° C., 520° C. and 700° C., 540° C. and 700° C., 560° C. and 700° C., 580° C. and 700° C., 600° C. and 700° C., 620° C. and 700° C., 640° C. and 700° C., 660° C. and 700° C., or 680° C. and 700° C. In other embodiments, the deposition temperature may be, for example, but not limited to, 400°C to 2000°C, 500°C to 2000°C, 550°C to 2400°C, 600°C to 2400°C, 625°C to 2400°C, 650°C to 2400°C, 675°C to 2400°C, 700°C to 2400°C, 725°C to 2400°C, 750°C to 2400°C, 775°C to 2400°C, 800°C to 2400°C, 900°C to 2400°C, 925°C to 2400°C, 950°C to 2400°C, 975 ... 400℃, 825℃~2400℃, 850℃~2400℃, 875℃~2400℃, 900℃~2400℃, 925℃~2400℃, 950℃~2400℃, 975℃~2400℃, 1000℃~2400℃, 1025℃~2400℃, 1050℃~2400℃, 1075℃~2400℃, 1100℃~2400℃, 1200℃~2400℃, 1 300℃~2400℃, 1400℃~2400℃, 1500℃~2400℃, 1600℃~2400℃, 1700℃~2400℃, 1800℃~2400℃, 1900℃~2400℃, 2000℃~2400℃, 2100℃~2400℃, 2200℃~2400℃, 2300℃~2400℃, 500℃~2000℃, 500℃~1900℃, 5 The temperature may be greater than 200°C to 2500°C, such as 500°C to 1800°C, 500°C to 1700°C, 500°C to 1600°C, 500°C to 1500°C, 500°C to 1400°C, 500°C to 1300°C, 500°C to 1200°C, 500°C to 1100°C, 500°C to 1000°C, 500°C to 1000°C, 500°C to 900°C, or 500°C to 800°C.

[0080]

[0116] Vapor deposition conditions can include, consist of, or consist essentially of a deposition pressure. In some embodiments, the deposition pressure can include, consist of, or consist essentially of the vapor pressure of at least one of the vaporized precursor, at least one vaporized co-reactant precursor, or any combination thereof. In some embodiments, the deposition pressure can include, consist of, or consist essentially of the chamber pressure.

[0081]

[0117] The deposition pressure can be a pressure between 0.001 Torr and 100 Torr. For example, in some embodiments, the deposition pressure can be a pressure between 1 Torr and 30 Torr, 1 Torr and 25 Torr, 1 Torr and 20 Torr, 1 Torr and 15 Torr, 1 Torr and 10 Torr, 5 Torr and 50 Torr, 5 Torr and 40 Torr, 5 Torr and 30 Torr, 5 Torr and 20 Torr, or 5 Torr and 15 Torr. In other embodiments, the deposition pressure is between 1 Torr and 100 Torr, between 5 Torr and 100 Torr, between 10 Torr and 100 Torr, between 15 Torr and 100 Torr, between 20 Torr and 100 Torr, between 25 Torr and 100 Torr, between 30 Torr and 100 Torr, between 35 Torr and 100 Torr, between 40 Torr and 100 Torr, between 45 Torr and 100 Torr, between 50 Torr and 100 Torr, between 55 Torr and 100 Torr, between 60 Torr and The pressure may be 100 Torr, 65 Torr to 100 Torr, 70 Torr to 100 Torr, 75 Torr to 100 Torr, 80 Torr to 100 Torr, 85 Torr to 100 Torr, 90 Torr to 100 Torr, 95 Torr to 100 Torr, 1 Torr to 95 Torr, 1 Torr to 90 Torr, 1 Torr to 85 Torr, 1 Torr to 80 Torr, 1 Torr to 75 Torr, or 1 Torr to 70 Torr. In other further embodiments, the deposition pressure can be a pressure between 1 mTorr and 100 mTorr, between 1 mTorr and 90 mTorr, between 1 mTorr and 80 mTorr, between 1 mTorr and 70 mTorr, between 1 mTorr and 60 mTorr, between 1 mTorr and 50 mTorr, between 1 mTorr and 40 mTorr, between 1 mTorr and 30 mTorr, between 1 mTorr and 20 mTorr, between 1 mTorr and 10 mTorr, between 100 mTorr and 300 mTorr, between 150 mTorr and 300 mTorr, between 200 mTorr and 300 mTorr, or between 150 mTorr and 250 mTorr, or between 150 mTorr and 225 mTorr.

[0082]

[0118] The substrate may comprise, consist of, or consist essentially of at least one of Si, Co, Cu, Al, W, WN, WC, TiN, Mo, MoC, SiO2, W, SiN, WCN, Al2O3, AlN, ZrO2, La2O3, TaN, RuO2, IrO2, Nb2O3, YO3, hafnium oxide, or any combination thereof.

[0083]

[0119] The tin-containing film can comprise tin oxide or a tin oxide film. In some embodiments, the tin-containing film comprises a functionalized tin oxide. In some embodiments, the tin-containing film has the formula: RSnO z wherein z is 1 to 6. In some embodiments, R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, or any combination thereof.

[0084]

[0120] In some embodiments, the present invention relates to a tin-containing film on a surface of a substrate. In some embodiments, the tin-containing film includes any film formed according to the methods disclosed herein. In some embodiments, the tin-containing film includes any film prepared from a precursor disclosed herein. [Example]

[0085] Example 1 Synthesis of Me3SiCH2Sn(NMe2)3 TIFF2025537025000026.tif134170

[0121] [Sn(N(CH3)2)2]2 (20.0 g, 48.1 mmol) was placed in a 500 mL Schlenk flask equipped with a magnetic stir bar and diluted with 250 mL of hexane. 1CH2Si(CH3)3 (10.8 g, 50.5 mmol) was diluted with 5 mL of hexane and added directly to the [Sn(N(CH3)2)2]2 solution with stirring. After the addition was complete, the reaction was stirred at 60 °C, and after 30 min the reaction mixture turned pale yellow. After heating for 16 h, the reaction mixture was cooled to room temperature and turned pale yellow with a crystalline pale yellow precipitate. The mother liquor was filtered through a disposable polyethylene filter frit into a 500 mL Schlenk flask, and the resulting pale yellow solution was dried under reduced pressure to give crude (CH3)3SiCH2Sn(N(CH3)2)3 as a pale yellow liquid. The product was distilled under reduced pressure (42-49°C, 190-160 mTorr) and collected as a colorless liquid. Mass: 6.15 g (37.9% yield). Purity: 119 Sn-NMR shows 99.59%. 1 H{ 13 C}-NMR(400MHz, C6D6, 298K):-0.02(s,2H);0.06(s,9H);2.73(s,18H)ppm; 13 C{ 1 H}-NMR(100MHz,C6D6,298K):-4.30,1.27,43.07ppm; 29 Si-NMR(79MHz,C6D6,298K):2.57ppm; 119 Sn{ 1 H}-NMR(149MHz,C6D6,298K):-17.21ppm.

[0086] Example 2 Synthesis of (CH3)2N(CH2)3Sn(N(CH3)2)3 TIFF2025537025000027.tif157170

[0122] [Sn(N(CH3)2)2]2 (2.0 g, 4.81 mmol) was placed in a 40 mL amber vial equipped with a magnetic stir bar and dissolved in 20 mL of hexane. Separately, 1,3-diiodopropane was diluted with 5 mL of hexane and added dropwise to the [Sn(N(CH3)2)2]2 solution over 2 minutes with stirring. After the addition was complete, the reaction was stirred at 60 °C. After 12 hours, the reaction, which showed a yellow mixture, was filtered through a disposable polyethylene filter frit. The vial and filter cake were washed with 2 mL of hexane, and the combined organics were dried under reduced pressure to give (CH3)2N(CH2)3Sn(N(CH3)2)3 as a yellow liquid. Mass: 0.68 g, Yield: 41.9%. 1 H{ 13 C}-NMR(400MHz, C6D6, 298K):1.13(t,2H);1.68(quintet,2H);2.05(s,6H);2.12(t,2H);2.77(s,18H)ppm; 13 C{ 1 H}-NMR(100MHz,C6D6,298K):9.61,23.75,43.41,45.59,62.61ppm; 119 Sn{ 1 H}-NMR(149MHz,C6D6,298K):-39.89ppm.

[0087]

[0123] Aspects

[0124] Various aspects are described below. It should be understood that any one or more of the features listed in the following aspects can be combined with any one or more other aspects. Aspect 1. Formula: 1. A composition comprising a precursor of TIFF2025537025000028.tif35170, During the ceremony, R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; L 1 , L 2 and L 3are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate; composition. Embodiment 2. The composition of embodiment 1, wherein the precursor has a purity of at least 99%. Aspect 3. The composition of Aspect 1 or 2, wherein R is —CH 3 or —CH(CH 3 ) 2 . Aspect 4. The composition of any one of Aspects 1 to 3, wherein R is —C 6 H 5 . Aspect 5. The composition of any one of aspects 1 to 4, wherein R is —CH 2 (C 6 H 5 ). Aspect 6. The composition of any one of aspects 1 to 5, wherein R is —CH 2 N(CH 3 ) 2 or —(CH 2 ) 3 N(CH 3 ) 2 . Aspect 7. The composition of any one of aspects 1 to 6, wherein R is —CH 2 CH 2 OCH 3 . Aspect 8. The composition of any one of aspects 1 to 7, wherein R is —CH 2 Si(CH 3 ) 3 . Embodiment 9. The composition of any one of embodiments 1 to 8, wherein R is —Si(CH 3 ) 3 . Aspect 10.L 1 , L 2 and L 3 but, independently of each other, At least one of TIFF2025537025000029.tif223170TIFF2025537025000030.tif148170, During the ceremony, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; 10. The method of any one of aspects 1 to 9. Aspect 11.L 1 , L2 or L 3 Aspect 11. The composition of any one of aspects 1 to 10, wherein is —N(CH 3 ) 2 . Aspect 12. The precursor has the chemical structure: 12. The composition of any one of embodiments 1 to 11, having TIFF2025537025000031.tif49170. Aspect 13. The precursor has the chemical structure: 13. The composition of any one of embodiments 1 to 12, having TIFF2025537025000032.tif61170. Aspect 14. Obtaining a tin compound and obtaining a halogen compound; A tin compound is contacted with a halogen compound to form a compound of the formula: forming a precursor of TIFF2025537025000033.tif35170; During the ceremony, R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; L 1 , L 2 and L 3 are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate; method. Embodiment 15. The tin compound comprises at least one compound of the formula: SnL2; Each L is independently 1 , L 2 or L 3 and L 1 , L 2 or L 3 are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate; 15. The method of embodiment 14. Aspect 16.L 1 , L 2 and L 3 but, independently of each other, At least one of TIFF2025537025000034.tif223170TIFF2025537025000035.tif148170, During the ceremony, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; 16. The method according to embodiment 14 or 15. 17. A halogen compound having the formula: The compound is TIFF2025537025000036.tif7170. During the ceremony, R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; X is Cl, Br, F or I; 17. The method of any one of embodiments 14 to 16. Aspect 18. The method of any one of Aspects 14 to 17, wherein the tin compound and the halogen compound are contacted in a solvent. Embodiment 19. The method of embodiment 18, wherein the solvent comprises hexane. Embodiment 20. The method of any one of embodiments 14 to 19, wherein the contacting is carried out under heating at a temperature in the range of 30°C to 150°C. Embodiment 21. Obtaining a precursor, The precursor has the formula: TIFF2025537025000037.tif35170, During the ceremony, R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; L1 , L 2 and L 3 are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate; Obtaining a precursor; obtaining at least one coreactant precursor; vaporizing the precursor to obtain a vaporized precursor; vaporizing at least one co-reactant precursor to obtain at least one vaporized co-reactant precursor; contacting at least one of the vaporized precursor, at least one vaporized co-reactant precursor, or any combination thereof, with a substrate under vapor deposition conditions to form a tin-containing film on the substrate; A method comprising: Embodiment 22 The method of embodiment 21, wherein the precursor has a purity of at least 99%. Aspect 23. The method of aspect 21 or 2, wherein R is —CH 3 or —CH(CH 3 ) 2 . Embodiment 24. The method of any one of embodiments 21 to 23, wherein R is —C 6 H 5 . Embodiment 25. The method of any one of embodiments 21 to 24, wherein R is —CH 2 (C 6 H 5 ). Aspect 26. A method according to any one of aspects 21 to 25, wherein R is -CH2N(CH3)2 or -(CH2)3N(CH3)2. Embodiment 27. The method of any one of embodiments 21 to 26, wherein R is —CH 2 CH 2 OCH 3 . Embodiment 28. The method of any one of embodiments 21 to 27, wherein R is —CH 2 Si(CH 3 ) 3 . Embodiment 29. The method of any one of embodiments 21 to 28, wherein R is —Si(CH 3 ) 3 . Aspect 30.L 1 , L 2 and L 3 but, independently of each other, At least one of TIFF2025537025000038.tif223170TIFF2025537025000039.tif148170, During the ceremony, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; 30. The method of any one of embodiments 21 to 29. Aspect 31.L 1 , L 2 or L 3 Aspect 31. The method of any one of aspects 21 to 30, wherein is —N(CH 3 ) 2 . Aspect 32. The precursor has the chemical structure: 32. The method of any one of embodiments 21 to 31, having TIFF2025537025000040.tif49170. Aspect 33. The precursor has the chemical structure: 33. The method of any one of embodiments 21 to 32, having TIFF2025537025000041.tif61170. It will be understood that changes in detail may be made, particularly in matters of materials of construction employed and shape, size and arrangement of parts, without departing from the scope of the present disclosure. The specification and described embodiments are exemplary, with the true scope and spirit of the present disclosure being indicated by the appended claims.

Claims

1. formula: a precursor of During the ceremony, R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; L １ , L ２ and L ３ are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate; composition.

2. The composition of claim 1 , wherein the precursor has a purity of at least 99%.

3. R is -CH ３ or -CH(CH ３ ) ２ The composition of claim 1 ,

4. R is -C ６ H ５ The composition of claim 1 ,

5. R is -CH ２ (C ６ H ５ 2. The composition of claim 1, wherein

6. R is -CH ２ N (CH ３ ) ２ or -(CH ２ ) ３ N (CH ３ ) ２ The composition of claim 1 ,

7. R is -CH ２ CH ２ OCH ３ The composition of claim 1 ,

8. R is -CH ２ Si(CH ３ ) ３ The composition of claim 1 ,

9. R is -Si(CH ３ ) ３ The composition of claim 1 ,

10. L １ , L ２ and L ３ but, independently of each other, the following: at least one of During the ceremony, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ and R １０ are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; The composition of claim 1.

11. L １ , L ２ or L ３ But -N(CH ３ ) ２ The composition of claim 1 ,

12. The precursor has the chemical structure:

10. The composition of claim 1, wherein

13. The precursor has the chemical structure:

10. The composition of claim 1, wherein

14. obtaining a tin compound; obtaining a halogen compound; The tin compound and the halogen compound are contacted to form a compound of the formula: forming a precursor of Including, During the ceremony, R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; L １ , L ２ and L ３ are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate; method.

15. The tin compound has the formula: SnL ２ and Each L is independently L １ , L ２ or L ３ and L １ , L ２ or L ３ are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate; 15. The method of claim 14.

16. L １ , L ２ and L ３ but, independently of each other, the following: at least one of During the ceremony, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ and R １０ are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; 15. The method of claim 14.

17. The halogen compound has the formula: is a compound of During the ceremony, R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; X is Cl, Br, F or I; 15. The method of claim 14.

18. 15. The method of claim 14, wherein the tin compound and the halogen compound are contacted in a solvent.

19. 20. The method of claim 18, wherein the solvent comprises hexane.

20. 15. The method of claim 14, wherein the contacting is carried out under heating at a temperature in the range of 30°C to 150°C.

21. Obtaining a precursor, The precursor has the formula: and During the ceremony, R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; L １ , L ２ and L ３ are each independently an amide, alkoxide, acetylide, carbamate, or carboxylate; Obtaining a precursor; obtaining at least one coreactant precursor; vaporizing the precursor to obtain a vaporized precursor; vaporizing the at least one co-reactant precursor to obtain at least one vaporized co-reactant precursor; contacting at least one of the vaporized precursor, the at least one vaporized co-reactant precursor, or any combination thereof, with a substrate under vapor deposition conditions to form a tin-containing film on the substrate; A method comprising:

22. 22. The method of claim 21, wherein the precursor has a purity of at least 99%.

23. R is -CH ３ or -CH(CH ３ ) ２ 22. The method of claim 21, wherein:

24. R is -C ６ H ５ 22. The method of claim 21, wherein:

25. R is -CH ２ (C ６ H ５ 22. The method of claim 21 , wherein

26. R is -CH ２ N (CH ３ ) ２ or -(CH ２ ) ３ N (CH ３ ) ２ 22. The method of claim 21, wherein:

27. R is -CH ２ CH ２ OCH ３ 22. The method of claim 21, wherein:

28. R is -CH ２ Si(CH ３ ) ３ 22. The method of claim 21, wherein:

29. R is -Si(CH ３ ) ３ 22. The method of claim 21, wherein:

30. L １ , L ２ and L ３ but, independently of each other, the following: at least one of During the ceremony, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ and R １０ are each independently alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, or aralkyl; 22. The method of claim 21.

31. L １ , L ２ or L ３ But -N(CH ３ ) ２ 22. The method of claim 21, wherein:

32. The precursor has the chemical structure:

22. The method of claim 21, comprising:

33. The precursor has the chemical structure:

22. The method of claim 21, comprising:

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