Disilylamine precursors and related methods

Abstract

A composition comprising a disilylamine precursor, the disilylamine precursor comprising a functional group attached to a nitrogen atom of the disilylamine precursor, the functional group comprising alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl. Related methods are provided, including methods for forming the disilylamine precursor, and methods for vapor deposition.

Description

[Technical Field]

[0001] This disclosure relates to disilylamine precursors for vapor deposition processes and related methods. [Background technology]

[0002] Vapor deposition processes use precursors that are vaporized and deposited as a film on a substrate. Summary of the Invention

[0003]

[0003] Some embodiments relate to precursors. In some embodiments, the precursors have the formula: Contains compound TIFF2025536763000002.tif43170,

[0004] During the ceremony,

[0005] R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0006] R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0007] R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0008] R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0009] R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0010] R 6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0011] R 7is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl.

[0004]

[0012] Some embodiments relate to a method for forming a precursor. In some embodiments, the method includes obtaining an amine compound. In some embodiments, the method includes obtaining at least one silylhalide compound. In some embodiments, the method includes contacting the amine compound with the at least one silylhalide compound to form a precursor. In some embodiments, the precursor has the formula: The compound is TIFF2025536763000003.tif43170.

[0013] During the ceremony,

[0014] R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0015] R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0016] R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0017] R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0018] R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0019] R 6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0020] R 7 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl.

[0005]

[0021] Some embodiments relate to methods for vapor deposition. In some embodiments, the methods include obtaining a precursor. In some embodiments, the precursor has the formula: Contains compound TIFF2025536763000004.tif43170,

[0022] During the ceremony,

[0023] R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0024] R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0025] R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0026] R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0027] R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0028] R 6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0029] R 7 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl. In some embodiments, the method includes vaporizing the precursor to obtain a vaporized precursor. In some embodiments, the method includes contacting the vaporized precursor with a substrate under vapor deposition conditions to form a silicon-containing film on the substrate.

[0006]

[0030] 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]

[0007] [Figure 1]

[0031] FIG. 1 is a flow diagram of a method for forming a precursor, according to some embodiments. [Figure 2]

[0032] FIG. 1 is a flow diagram of a method for making a silicon-containing film, according to some embodiments. [Figure 3]

[0033] FIG. 2 is a schematic diagram of a reaction scheme for forming a precursor, according to some embodiments. [Figure 4]

[0034] FIG. 2 is a schematic diagram of a reaction scheme for forming a precursor, according to some embodiments. [Figure 5]

[0035] 1 is a proton nuclear magnetic resonance spectrum ( 1 H NMR) of a precursor according to some embodiments. [Figure 6]

[0036] 1 is a proton nuclear magnetic resonance spectrum ( 1 H NMR) of a precursor according to some embodiments. [Figure 7]

[0037] 1 is a proton nuclear magnetic resonance spectrum ( 1 H NMR) of a precursor according to some embodiments. [Figure 8]

[0038] 1 is a proton nuclear magnetic resonance spectrum ( 1 H NMR) of a precursor according to some embodiments. DETAILED DESCRIPTION OF THE INVENTION

[0008]

[0039] 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.

[0009]

[0040] All prior patents and publications referenced herein are incorporated by reference in their entirety.

[0010]

[0041] 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.

[0011]

[0042] As used herein, the term "based on" is not exclusive and allows for the use of additional unlisted factors unless the context clearly dictates otherwise. Additionally, throughout this specification, the meanings of "a," "an," and "the" include plural references. The meaning of "in" includes "in" and "on."

[0012]

[0043] 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 nFor 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 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, 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 10The alkyl may comprise, consist essentially of, or 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, C3-C4 alkyl, or any combination thereof. In some embodiments, the alkyl is a linear C1-C4 alkyl. In some embodiments, the alkyl is a branched C3-C4 alkyl. In some embodiments, alkyl can comprise, consist of, consist essentially of, or be selected from the group consisting of at least one of methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, isobutyl, sec-butyl, n-pentyl, 1,1-dimethylethyl (t-butyl), n-pentyl, isopentyl, n-hexyl, isohexyl, 3-methylhexyl, 2-methylhexyl, octyl, decyl, dodecyl, octadecyl, or any combination thereof. In some embodiments, alkyl is substituted with one or more substituents.

[0013]

[0044] As used herein, the term "alkenyl" refers to a hydrocarbyl having 1 to 10 carbon atoms and at least one carbon-carbon double bond. 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, In some embodiments, the alkenyl is substituted with one or more substituents, and the alkenyl may be 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.

[0014]

[0045] As used herein, the term "alkynyl" refers to a hydrocarbyl having 1 to 10 carbon atoms and at least one carbon-carbon triple bond. Examples of alkynyl groups include, but are not limited to, at least one of ethynyl, propynyl, n-butynyl, n-pentynyl, 3-methyl-1-butynyl, n-hexynyl, methyl-pentynyl, or any combination thereof. In some embodiments, the alkynyl is substituted with one or more substituents.

[0015]

[0046] As used herein, the term "cycloalkyl" refers to a non-aromatic carbocyclic ring having 3 to 8 carbon atoms within the ring. In some embodiments, cycloalkyl includes C3-C6 cycloalkyl. In some embodiments, cycloalkyl includes C3-C5 cycloalkyl. In some embodiments, cycloalkyl includes C3-C4 cycloalkyl. The term includes monocyclic non-aromatic carbocyclic rings and polycyclic non-aromatic carbocyclic rings. 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, cycloalkyl can comprise, 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. In some embodiments, cycloalkyl is substituted with one or more substituents.

[0016]

[0047] 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 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. Examples of aryl include, but are not limited to, phenyl, biphenyl, naphthyl, and the like. In some embodiments, an aryl includes benzyl. In some embodiments, an aryl is substituted with one or more substituents.

[0017]

[0048] Non-limiting examples of aryl include, but are not limited to, benzene, toluene, xylene (e.g., o-xylene, m-xylene, p-xylene), t-butyltoluene (e.g., ot-butyltoluene, mt-butyltoluene, pt-butyltoluene), ethylmethylbenzene (e.g., 1-ethyl-4-methylbenzene, 1-ethyl-3-methylbenzene), 1-isopropyl-4-methylbenzene, 1-t-butyl-4-methylbenzene, mesitylene, pseudocumene, durene, methylbenzene, dimethylbenzene, trimethylbenzene, ethylbenzene, and at least one of benzene, diethylbenzene (e.g., 1,4-diethylbenzene), triethylbenzene, propylbenzene, butylbenzene, iso-butylbenzene, sec-butylbenzene, t-butylbenzene, hexylbenzene, styrene, naphthalene, anthracene, phenanthrene, biphenyl, terphenyl, methylnaphthalene, biphenylene, dimethylnaphthalene, methylanthracene, 4,4′-dimethylbiphenyl, bibenzyl, diphenylmethane, any isomer thereof, or any combination thereof.

[0018]

[0049] As used herein, the term "amine" refers to an amine having the formula -N(R a R b R c ) functional group, in which R a , R b and R c each is independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl, or R a , R b and R c two of R are linked to form a 3- to 6-membered ring. a , R b or R c is hydrogen, the amine has the formula: -NH(R b R c) functional group. In some embodiments, the term "amine" includes amino, 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 alkylamine, a dialkylamine, or a trialkylamine. 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 amines include, but are not limited to, primary amines, 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; secondary amines, such as, but not limited to, dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diisobutylamine, di-se c-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; and tertiary amines such as, but not limited to, one or more of trimethylamine, triethylamine, tripropylamine, tributylamine, tripentylamine, dimethylethylamine, methyldiethylamine, and methyldipropylamine.Examples of polyamines may include, but are not limited to, one or more of the following: ethylenediamine, propylenediamine, trimethylenediamine, tetramethylenediamine, 1,3-diaminobutane, 2,3-diaminobutane, pentamethylenediamine, 2,4-diaminopentane, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, N-methylethylenediamine, N,N-dimethylethylenediamine, trimethylethylenediamine, N-ethylethylenediamine, N,N-diethylethylenediamine, triethylethylenediamine, 1,2,3-triaminopropane, hydrazine, tris(2-aminoethyl)amine, tetra(aminomethyl)methane, diethylenetriamine, triethylenetetramine, tetraethylpentamine, heptaethyleneoctamine, nonaethylenedecamine, and diazabicycloundecene. In some embodiments, the amine is substituted with one or more substituents.

[0019]

[0050] In some embodiments, the polyamine compound comprises, consists of, consists essentially of, or is selected from the group consisting of at least one of ethylenediamine, propylenediamine, trimethylenediamine, triethylenediamine, methylpentanediamine, tetramethylenediamine, 1,3-diaminobutane, 2,3-diaminobutane, pentamethylenediamine, 2,4-diaminopentane, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, 1,2,3-triaminopropane, hydrazine, tetra(aminomethyl)methane, or any combination thereof. In some embodiments, the polyamine compound comprises, consists of, consists essentially of, or is selected from the group consisting of at least one of N-methylethylenediamine, N,N-dimethylethylenediamine, trimethylethylenediamine, N-ethylethylenediamine, N,N-diethylethylenediamine, triethylethylenediamine, or any combination thereof. In some embodiments, the polyamine compound is selected from the group comprising, consisting of, consisting essentially of, or comprising at least one of tris(2-aminoethyl)amine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, heptaethyleneoctamine, nonaethylenedecamine, N',N'-bis(2-aminoethyl)ethane-1,2-diamine, or any combination thereof. In some embodiments, the polyamine compound comprises at least one of 1,2-ethanediamine; 1,2-propanediamine; 1,3-propanediamine; 1,4-butanediamine; 1,6-hexanediamine; 2-methyl-1,5-pentanediamine; 2,2(4),4-trimethylhexanediamine; 2,2,4-trimethyl-1,6-hexanediamine; 2,4,4-trimethyl-1,6-hexanediamine; or any combination thereof.

[0020]

[0051] As used herein, the term "contacting" refers to direct contact or immediate proximity or closeness. In some embodiments, contacting is sufficient to cause two or more components to react. The term "contacting" includes, for example, but is not limited to, at least one of mixing, combining, reacting, adding, dissolving, solubilizing, or any combination thereof.

[0021]

[0052] As used herein, the term "silicon-containing film" refers to a film containing at least one of silicon, silicon nitride, silicon oxynitride, silicon oxide, silicon dioxide, silicon carbide, silicon carbonitride, silicon oxycarbonitride, carbon-doped silicon nitride, carbon-doped silicon oxide, carbon-doped silicon oxynitride, or any combination thereof. For example, the silicon-containing film can include at least one of SiO film, SiN film, SiOC film, SiCN film, SiOCN film, or any combination thereof. In some embodiments, the silicon-containing film has a thickness of 20 Å to 2000 Å.

[0022]

[0053] Some embodiments relate to disilylamine precursors and related methods. At least some of these embodiments relate to disilylamine precursors useful in the manufacture of microelectronic devices, including semiconductor devices. For example, the disilylamine precursors can be used to form silicon-containing films by one or more deposition processes. 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.

[0023]

[0054] Disilylamine precursors, including but not limited to, aminosilanes, are provided that are useful for thin film deposition. The disilylamine precursors disclosed herein can exist in a liquid state at room temperature and atmospheric pressure. The disilylamine precursors disclosed herein can exhibit improved atomic layer deposition SiO2 growth rates compared to conventional precursors. The disilylamine precursors may not produce undesirable reaction by-products and impurities. In some embodiments, the disilylamine precursors exhibit excellent low-temperature SiO2 growth using plasma-enhanced atomic layer deposition processes and thermal atomic layer deposition processes. Furthermore, the disilylamine precursors are halogen-free and highly pure. The disilylamine precursors disclosed herein can be useful for forming high-quality, high-growth-rate silicon-containing films, including but not limited to, SiO, SiN, SiOC, SiCN, and SiOCN, at low temperatures.

[0024]

[0055] In some embodiments, the precursor has the formula: Contains compound TIFF2025536763000005.tif43170,

[0056] During the ceremony,

[0057] R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0058] R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0059] R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0060] R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0061] R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0062] R 6is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0063] R 7 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl.

[0025]

[0064] In some embodiments, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 or any combination thereof does not contain silicon. 1 does not contain silicon. In some embodiments, R 2 does not contain silicon. In some embodiments, R 3 does not contain silicon. In some embodiments, R 4 does not contain silicon. In some embodiments, R 5 does not contain silicon. In some embodiments, R 6 does not contain silicon. In some embodiments, R 7 does not contain silicon.

[0026]

[0065] In some embodiments, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 7 or any combination thereof, at least one of R 2 is not hydrogen. In some embodiments, R 3 is not hydrogen. In some embodiments, R 4 is not hydrogen. In some embodiments, R 5 is not hydrogen. In some embodiments, R 6 is not hydrogen. In some embodiments, R 7 is not hydrogen. In some embodiments, R2 , R 3 and R 4 is not hydrogen. In some embodiments, R 5 , R 6 and R 7 is not hydrogen.

[0027]

[0066] In some embodiments, the precursor does not include a halide, hi some embodiments, the precursor does not include at least one of F, Cl, Br, I, or any combination thereof.

[0028]

[0067] In some embodiments, the precursor is in the liquid phase at ambient temperature and pressure. In some embodiments, the disilylamine precursor is a liquid at a temperature of 20° C. to 30° C. In some embodiments, the disilylamine precursor is a liquid at atmospheric pressure.

[0029]

[0068] Examples of precursors include, but are not limited to, the following structures: TIFF2025536763000006.tif194170TIFF2025536763000007.tif229170TIFF2025536763000008.tif243170TIFF2025536763000009.tif133170.

[0030]

[0069] FIG. 1 is a flow diagram of a method 100 for forming a precursor, according to some embodiments. In some embodiments, method 100 is useful for forming any of the precursors disclosed herein. As shown in FIG. 1 , the method for forming the precursor may include, consist of, or consist essentially of, one or more of the following steps, in any order: step 102 of obtaining an amine compound; step 104 of obtaining at least one silyl halide compound; and step 106 of contacting the amine compound with at least one silyl halide compound to form a precursor. In some embodiments, method 100 proceeds entirely in the liquid phase. In some embodiments, the resulting precursor is a liquid. In some embodiments, the amine compound is a liquid. In some embodiments, the silyl halide compound is a liquid.

[0031]

[0070] In step 102, in some embodiments, method 100 includes obtaining an amine compound. In some embodiments, the amine compound has the formula: Contains compound TIFF2025536763000010.tif8170,

[0071] During the ceremony,

[0072] R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl.

[0032]

[0073] In some embodiments, R 1 does not contain silicon. In some embodiments, R 1 does not contain halides.

[0033]

[0074] In step 104, in some embodiments, the method includes obtaining at least one silyl halide compound. In some embodiments, the at least one silyl halide compound has the formula: Contains compound TIFF2025536763000011.tif36170,

[0075] During the ceremony,

[0076] X1 is F, Cl, Br or I;

[0077] R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or benzyl;

[0078] R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or benzyl;

[0079] R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl.

[0034]

[0080] In some embodiments, R 2 , R 3 , R 4 or any combination thereof does not contain silicon. 2 does not contain silicon. In some embodiments, R 3 does not contain silicon. In some embodiments, R 4 does not contain silicon.

[0035]

[0081] In some embodiments, R 2 , R 3 , R 4 or any combination thereof, at least one of R 2 is not hydrogen. In some embodiments, R 3 does not contain hydrogen. In some embodiments, R 4 does not contain hydrogen. In some embodiments, R 2 , R 3 and R 4 is not hydrogen.

[0036]

[0082] In some embodiments, the at least one silyl halide compound does not contain a halide. In some embodiments, the at least one silyl halide compound does not contain at least one of F, Cl, Br, I, or any combination thereof.

[0037]

[0083] In some embodiments, at least one silyl halide compound has the formula: Contains compound TIFF2025536763000012.tif36170,

[0084] During the ceremony,

[0085] X2 is F, Cl, Br or I;

[0086] R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or benzyl;

[0087] R 6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or benzyl;

[0088] R 7 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl.

[0038]

[0089] In some embodiments, R 5 , R 6 , R 7 or any combination thereof does not contain silicon. 5 does not contain silicon. In some embodiments, R 6 does not contain silicon. In some embodiments, R 7 does not contain silicon.

[0039]

[0090] In some embodiments, R 5 , R 6 , R 7 or any combination thereof, at least one of R 5 is not hydrogen. In some embodiments, R 6 is not hydrogen. In some embodiments, R 7 does not contain hydrogen. In some embodiments, R 5 , R 6 and R 7 is not hydrogen.

[0040]

[0091] In some embodiments, the at least one silyl halide compound does not contain a halide. In some embodiments, the at least one silyl halide compound does not contain at least one of F, Cl, Br, I, or any combination thereof.

[0041]

[0092] In some embodiments, the molar ratio of the amine compound to the silyl halide compound is at least 1:1. In some embodiments, the molar ratio of the amine compound to the silyl halide compound is from 1:1 to 1:10, or any range or subrange therebetween. In some embodiments, the molar ratio of the amine compound to the silyl halide compound is from 1:1 to 1:10, 1:1 to 1:9, 1:1 to 1:8, 1:1 to 1:7, 1:1 to 1:6, 1:1 to 1:5, 1:1 to 1:4, 1:1 to 1:3, or 1:1 to 1:2.

[0042]

[0093] In step 106, in some embodiments, the method 100 includes contacting an amine compound with at least one silyl halide compound.

[0043]

[0094] In some embodiments, contacting comprises direct contacting or immediate proximity or close proximity. In some embodiments, contacting comprises combining or adding to a reaction flask, reaction vial, or reactor. In some embodiments, contacting comprises at least one of dissolving, solubilizing, reacting, or stirring. In some embodiments, contacting comprises dropwise addition.

[0044]

[0095] In some embodiments, the amine compound is contacted with only one silyl halide compound. In some embodiments, the amine compound is contacted with two or more silyl halide compounds. In some embodiments, for example, the amine compound is contacted with a first silyl halide compound to form an intermediate. In some embodiments, the intermediate is contacted with a second silyl halide compound to form a precursor. Any of the silyl halide compounds disclosed herein can be employed as the silyl halide compound, the first silyl halide compound, the second silyl halide compound, or any combination thereof without departing from the scope of the present disclosure.

[0045]

[0096] In some embodiments, the first silyl halide compound has the formula: Contains compound TIFF2025536763000013.tif36170,

[0097] During the ceremony,

[0098] X1 is F, Cl, Br or I;

[0099] R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or benzyl;

[0100] R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or benzyl;

[0101] R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl.

[0046]

[0102] In some embodiments, R 2 , R 3 , R 4 or any combination thereof does not contain silicon. 2 does not contain silicon. In some embodiments, R 3 does not contain silicon. In some embodiments, R 4 does not contain silicon.

[0047]

[0103] In some embodiments, R 2 , R 3 , R 4 or any combination thereof, at least one of R 2 is not hydrogen. In some embodiments, R 3 is not hydrogen. In some embodiments, R 4 does not contain hydrogen. In some embodiments, R 2 , R 3 and R 4 is not hydrogen.

[0048]

[0104] In some embodiments, the first silyl halide compound does not include a halide. In some embodiments, the first silyl halide compound does not include at least one of F, Cl, Br, I, or any combination thereof.

[0049]

[0105] In some embodiments, the intermediate has the formula: TIFF2025536763000014.tif36170 compound,

[0106] During the ceremony,

[0107] R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0108] R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0109] R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0110] R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl.

[0050]

[0111] In some embodiments, the second silyl halide compound has the formula: Contains compound TIFF2025536763000015.tif36170,

[0112] During the ceremony,

[0113] X2 is F, Cl, Br or I;

[0114] R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or benzyl;

[0115] R 6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or benzyl;

[0116] R 7 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl.

[0051]

[0117] In some embodiments, R 5 , R 6 , R 7 or any combination thereof does not contain silicon. 5 does not contain silicon. In some embodiments, R 6 does not contain silicon. In some embodiments, R 7 does not contain silicon.

[0052]

[0118] In some embodiments, R 5 , R 6 , R 7 or any combination thereof, at least one of R 5 is not hydrogen. In some embodiments, R 6 is not hydrogen. In some embodiments, R 7 is not hydrogen. In some embodiments, R 5 , R 6 and R 7 is not hydrogen.

[0053]

[0119] In some embodiments, the second silyl halide compound does not include a halide. In some embodiments, the second silyl halide compound does not include at least one of F, Cl, Br, I, or any combination thereof.

[0054]

[0120] In some embodiments, the precursor has the formula: Contains compound TIFF2025536763000016.tif43170,

[0121] During the ceremony,

[0122] R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0123] R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0124] R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0125] R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0126] R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0127] R 6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl;

[0128] R 7 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl.

[0055]

[0129] In some embodiments, the contacting proceeds in a solvent. In some embodiments, the solvent comprises at least one of CHCl, EtO, n-hexane, EtOAc, THF, or any combination thereof. In some embodiments, the contacting proceeds in the presence of an alkyllithium. In some embodiments, the alkyllithium comprises at least one of methyllithium, n-butyllithium, t-butyllithium, or any combination thereof.

[0056]

[0130] In some embodiments, the contacting is carried out at or under heating to a temperature within the range of -50°C to 50°C, or any range or subrange therebetween. In some embodiments, for example, the heating is carried out at a temperature of -50°C to 45°C, -50°C to 40°C, -50°C to 35°C, -50°C to 30°C, -50°C to 25°C, -50°C to 20°C, -50°C to 15°C, -50°C to 10°C, -50°C to 5°C, -50°C to 0°C, -50°C to -5°C, -50°C to -10°C, -50°C to -15°C, -50°C to -20°C, -50°C to -25°C, -50°C to -30°C, -50°C to -35°C, -50°C to -40°C, The reaction is carried out at or to a temperature within the range of -50°C to -45°C, -45°C to 50°C, -40°C to 50°C, -35°C to 50°C, -30°C to 50°C, -25°C to 50°C, -20°C to 50°C, -15°C to 50°C, -10°C to 50°C, -5°C to 50°C, 0°C to 50°C, 5°C to 50°C, 10°C to 50°C, 15°C to 50°C, 20°C to 50°C, 25°C to 50°C, 30°C to 50°C, 35°C to 50°C, 40°C to 50°C, or 45°C to 50°C.

[0057]

[0131] 2 is a flow diagram of a method 200 for making a silicon-containing film according to some embodiments. As shown in FIG. 2, the method 200 for making a silicon-containing film 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 silicon-containing film on the substrate.

[0058]

[0132] Step 202 can include, consist of, or consist essentially of obtaining a precursor. The precursor may include, consist of, or consist essentially of any one or more of the precursors disclosed herein. Obtaining may include obtaining a vessel or other container containing the precursor. In some embodiments, the precursor may be obtained in a vessel or other container in which the precursor is vaporized.

[0059]

[0133] 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 silicon-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.

[0060]

[0134] 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.

[0061]

[0135] 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.

[0062]

[0136] 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 silicon-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, for example, 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.

[0063]

[0137] 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.

[0064]

[0138] 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.

[0065]

[0139] The deposition temperature can be from 200° C. to 2500° C. In some embodiments, the deposition temperature can be from 500° C. to 700° C. For example, in some embodiments, the deposition temperature can be from 500° C. to 680° C., 500° C. to 660° C., 500° C. to 640° C., 500° C. to 620° C., 500° C. to 600° C., 500° C. to 580° C., 500° C. to 560° C., 500° C. to 540° C., 500° C. to 520° C., 520° C. to 700° C., 540° C. to 700° C., 560° C. to 700° C., 580° C. to 700° C., 600° C. to 700° C., 620° C. to 700° C., 640° C. to 700° C., 660° C. to 700° C., or 680° C. to 700° C. In other embodiments, the deposition temperature is from greater than 200° C. to 2500° C., 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℃ to 2400℃, 750℃ to 2400℃, 775℃ to 2400℃, 800℃ to 2400℃, 825℃ to 2400℃, 850℃ to 2400℃, 875℃ to 2400℃, 900℃ to 2400℃, 925℃ to 2400℃, 950℃ to 2400℃, 975℃ to 2400℃, 1000℃ to 2400℃, 1025℃ to 2400℃, 1050℃ to 2400℃, 1075℃ to 2400℃, 1100℃ to 2400℃, 1200℃ to 2400℃, 1300℃ to 2400℃, 1400℃ to 2400℃, 1500℃ to 2400℃, 1600℃ to 2400℃, 170 The temperature may be from 0°C to 2400°C, 1800°C to 2400°C, 1900°C to 2400°C, 2000°C to 2400°C, 2100°C to 2400°C, 2200°C to 2400°C, 2300°C to 2400°C, 500°C to 2000°C, 500°C to 1900°C, 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.

[0066]

[0140] 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.

[0067]

[0141] The deposition pressure can be a pressure of 0.001 Torr to 100 Torr. For example, in some embodiments, the deposition pressure can be a pressure of 1 Torr to 30 Torr, 1 Torr to 25 Torr, 1 Torr to 20 Torr, 1 Torr to 15 Torr, 1 Torr to 10 Torr, 5 Torr to 50 Torr, 5 Torr to 40 Torr, 5 Torr to 30 Torr, 5 Torr to 20 Torr, or 5 Torr to 15 Torr. In other embodiments, the deposition pressure is from 1 Torr to 100 Torr, 5 Torr to 100 Torr, 10 Torr to 100 Torr, 15 Torr to 100 Torr, 20 Torr to 100 Torr, 25 Torr to 100 Torr, 30 Torr to 100 Torr, 35 Torr to 100 Torr, 40 Torr to 100 Torr, 45 Torr to 100 Torr, 50 Torr to 100 Torr, 55 Torr to 100 Torr, 60 Torr to The pressure can 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 may be a pressure of 1 mTorr to 100 mTorr, 1 mTorr to 90 mTorr, 1 mTorr to 80 mTorr, 1 mTorr to 70 mTorr, 1 mTorr to 60 mTorr, 1 mTorr to 50 mTorr, 1 mTorr to 40 mTorr, 1 mTorr to 30 mTorr, 1 mTorr to 20 mTorr, 1 mTorr to 10 mTorr, 100 mTorr to 300 mTorr, 150 mTorr to 300 mTorr, 200 mTorr to 300 mTorr, or 150 mTorr to 250 mTorr, or 150 mTorr to 225 mTorr.

[0068]

[0142] 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. In some embodiments, the silicon-containing film may comprise, consist of, or consist essentially of at least one of silicon, silicon nitride, silicon oxynitride, silicon oxide, silicon dioxide, silicon carbide, silicon carbonitride, silicon oxycarbonitride, carbon-doped silicon nitride, carbon-doped silicon oxide, carbon-doped silicon oxynitride, or any combination thereof. In some embodiments, the substrate may comprise other silicon-based substrates, such as, for example, one or more of a polysilicon substrate, a metal substrate, and a dielectric substrate.

[0069]

[0143] Some embodiments relate to a silicon-containing film on the surface of a substrate. In some embodiments, the silicon-containing film comprises any film formed according to the methods disclosed herein. In some embodiments, the silicon-containing film comprises any film prepared from the precursors disclosed herein. [Example]

[0070] Example 1 Synthesis of bis(dimethylsilyl)cyclohexylamine TIFF2025536763000017.tif29170

[0144] Triethylamine (38.6 g, 0.381 mol) was added to (CH3)2SiHCl (35.2 g, 0.37 mol) in THF at 30 °C. Vapors were generated in the reactor immediately upon injection, and the mixture became cloudy. After 30 minutes of reaction time, cyclohexylamine (18.0 g, 0.182 mol) was added to the mixture. After 7 days of reaction time at room temperature, the mixture was filtered through a glass filter and flushed with THF. The conversion of cyclohexylamine to the precursor was determined by GC-FID analysis of the reaction mixture. The GC-FID distribution was approximately 97% single peak, with less than 3% impurities. Volatiles were removed using a distillation system at 200 to 300 Torr and an internal temperature of 35 to 50 °C. The product was distilled at 30 to 40 °C and 0.8 to 1 Torr to obtain 16.08 g of the precursor in 41% yield. The main product was 1 This was confirmed by 1 H NMR spectroscopy (Figure 5).

[0071] Example 2 Synthesis of bis(dimethylsilyl)(t-butyl)amine TIFF2025536763000018.tif28170

[0145] (CH3)2SiHCl (53.0 g, 0.56 mol) in THF was cooled to -40 °C and stirred for 30 minutes. tert-Butylamine (81.9 g, 1.12 mol) was added to the mixture, and the mixture was stirred overnight without cooling. The mixture was filtered through a glass filter and rinsed with THF. A 2.5 M solution of n-BuLi (224.1 mL, 0.56 mol) was added to the filtered mixture at 0 °C, and the mixture was stirred overnight without cooling. (CH3)2SiHCl (53.0 g, 0.56 mol) was added to the mixture at 0 °C, and the mixture was stirred overnight without cooling. The mixture was filtered through a glass filter, and the volatiles were removed at 200 to 300 Torr and an internal temperature of 30 to 35 °C. The concentrated mixture was filtered through a glass filter, and n-hex was added to remove impurities. The mixture was filtered through a glass filter, and the volatiles were removed in a distillation system at 200 to 300 Torr and an internal temperature of 35 to 35°C. The product was distilled at 40 to 45°C and 10 to 15 Torr to give 53.8 g of the precursor in an overall yield of 50.7%. The main product was 1This was confirmed by 1 H NMR spectroscopy (Figure 6).

[0072] Example 3 Synthesis of bis(dimethylsilyl)(isopropyl)amine TIFF2025536763000019.tif23170

[0146] Isopropylamine (26 g, 0.44 mol) was added to (CH3)2SiHCl (43.7 g, 0.46 mol) in THF at 30 °C, and the mixture was stirred overnight. Vapors were generated in the reactor immediately upon injection, and the mixture became cloudy. The mixture was filtered through a glass filter and flushed with THF. The conversion of isopropylamine to the precursor was determined by GC-FID analysis of the reaction mixture, which showed a nearly 99% single peak distribution with less than 1% impurities. Volatiles were removed using a distillation system at 100 to 200 Torr and an internal temperature of 30 to 40 °C. The product was distilled at 30 to 35 °C and 5 to 10 Torr to obtain 33.19 g of the precursor in 44% yield. The main product was 1 This was confirmed by 1 H NMR spectroscopy (Figure 7).

[0073] Example 4 Synthesis of N-ethylbis(dimethylsilyl)amine TIFF2025536763000020.tif23170

[0147] Ethylamine (8.2 g, 0.182 mol) was added to (CH3)2SiHCl (39.74 g, 0.42 mol) in THF at 30 °C, and the mixture was stirred overnight. Vapors were generated in the reactor immediately upon injection, and the mixture became cloudy. After a reaction time of 1 day at room temperature, the mixture was filtered through a glass filter and flushed with THF. The conversion of ethylamine to the precursor was determined by GC-FID analysis of the reaction mixture, which showed a nearly 98% single peak distribution with less than 2% impurities. Volatiles were removed using a distillation system at 150 to 200 Torr and an internal temperature of 35 to 40 °C. The product was distilled at 25 to 28 °C and 8 to 10 Torr to obtain 17.2 g of the precursor in 53.4% ​​yield. The main product was 1 This was confirmed by 1 H NMR spectroscopy (Figure 8).

[0074]

[0148] Aspects

[0149] 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. Embodiment 1. A precursor comprising: formula: Contains compound TIFF2025536763000021.tif43170, During the ceremony, R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 7 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; Precursor. Aspect 2.R 1 is alkyl. Aspect 3.R 1 is a linear C1-C4 alkyl. Aspect 4.R 1 A precursor according to any one of aspects 1 to 3, wherein is a branched C3-C4 alkyl. Aspect 5.R 1A precursor according to any one of aspects 1 to 4, wherein is cycloalkyl. Aspect 6.R 1 A precursor according to any one of aspects 1 to 5, wherein is C3-C6 cycloalkyl. Aspect 7.R 1 A precursor according to any one of aspects 1 to 6, wherein is aryl. Aspect 8.R 1 A precursor according to any one of aspects 1 to 7, wherein is benzyl. Aspect 9.R 1 Aspect 9. The precursor of any one of aspects 1 to 8, wherein Aspect 10.R 2 , R 3 , R 4 , R 5 , R 6 and R 7 but does not comprise silicon. Embodiment 11. The precursor of any one of embodiments 1 to 10, wherein the precursor does not contain a halide. Aspect 12. The precursor of any one of aspects 1 to 11, wherein the precursor is in a liquid phase at ambient temperature and pressure. Aspect 13. A compound comprising: 13. The precursor of any one of aspects 1 to 12, comprising at least one of: TIFF2025536763000022.tif194170 TIFF2025536763000023.tif229170 TIFF2025536763000024.tif243170 TIFF2025536763000025.tif133170; or any combination thereof. Embodiment 14. A method for forming a precursor, comprising: Obtaining an amine compound; obtaining at least one silyl halide compound; contacting an amine compound with at least one silyl halide compound to form a precursor; Including, The precursor has the formula: The compound is TIFF2025536763000026.tif43170. During the ceremony, R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 7 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; method. Aspect 15. The amine compound has the formula: The compound is TIFF2025536763000027.tif8170. During the ceremony, R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; 15. The method of embodiment 14. Embodiment 16. At least one silyl halide compound has the formula: TIFF2025536763000028.tif36170 compound, During the ceremony, X1 is F, Cl, Br or I; R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; 16. The method according to embodiment 14 or 15. 17. At least one silyl halide compound has the formula: TIFF2025536763000029.tif36170 compound, During the ceremony, X2 is F, Cl, Br or I; R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 7 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; 17. The method of any one of embodiments 14 to 16. Embodiment 18 The method of any one of embodiments 14 to 17, wherein the molar ratio of the amine compound to the silyl halide compound is at least 1:1. Embodiment 19 The method of any one of embodiments 14 to 18, wherein the molar ratio of the amine compound to the silyl halide compound is at least 1:2. Aspect 20. The contacting step comprises: contacting an amine compound with a first silyl halide compound to form an intermediate; contacting the intermediate with a second silyl halide compound to obtain a precursor; The intermediate is of the formula: TIFF2025536763000030.tif36170 compound, During the ceremony, R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; 20. The method of any one of embodiments 14 to 19. Embodiment 21. The method of any one of embodiments 14 to 20, wherein the contacting comprises contacting in a solvent, and the solvent comprises at least one of CH2Cl2, Et2O, n-hexane, EtOAc, THF, or any combination thereof. Embodiment 22 The method of any one of embodiments 14 to 21, wherein the contacting comprises contacting in the presence of an alkyllithium. Aspect 23. The method of aspect 22, wherein the alkyllithium comprises at least one of methyllithium, n-butyllithium, t-butyllithium, or any combination thereof. Aspect 24.R 1 24. The method of any one of embodiments 14 to 23, wherein Aspect 25.R 2 , R 3 , R 4 , R 5 , R 6 and R 7 25. The method of any one of aspects 14 to 24, wherein the silicon-containing polymer is silicon-free. Aspect 26 The method of any one of aspects 14 to 25, wherein the amine compound and the silyl halide compound are in a liquid phase. Embodiment 27. A method for vapor deposition, comprising: obtaining a precursor, the precursor having the formula: TIFF2025536763000031.tif43170[In the formula, R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 4 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 6 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R 7 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; obtaining a precursor comprising a compound of vaporizing the precursor to obtain a vaporized precursor; contacting the vaporized precursor with the substrate under vapor deposition conditions to form a silicon-containing film on the substrate; A method comprising: Embodiment 28. The method of embodiment 27, wherein the vapor deposition conditions comprise plasma-enhanced atomic layer deposition conditions. Embodiment 29 The method of embodiment 27 or 28, wherein the vapor deposition conditions comprise thermal atomic layer deposition conditions. Embodiment 30. The method of any one of embodiments 27 to 29, wherein the silicon-containing film comprises at least one of SiO, SiN, SiOC, SiCN, SiOCN, or any combination thereof. 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. A precursor comprising: formula: and During the ceremony, R １ is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ２ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ３ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ４ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ５ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ６ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ７ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; Precursor.

2. R １ The precursor of claim 1 , wherein is alkyl.

3. R １ is a linear C １ -C ４ The precursor of claim 1 , which is an alkyl.

4. R １ Branched C ３ -C ４ The precursor of claim 1 , which is an alkyl.

5. R １ The precursor of claim 1 , wherein is cycloalkyl.

6. R １ is C ３ -C ６ The precursor of claim 1 which is a cycloalkyl.

7. R １ The precursor of claim 1 , wherein is aryl.

8. R １ The precursor of claim 1 , wherein is benzyl.

9. R １ The precursor of claim 1 , wherein is silicon-free.

10. The following compounds: or any combination thereof.

11. 1. A method for forming a precursor, comprising: Obtaining an amine compound; obtaining at least one silyl halide compound; contacting the amine compound with the at least one silyl halide compound to form the precursor; Including, The precursor has the formula: is a compound of During the ceremony, R １ is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ２ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ３ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ４ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ５ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ６ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ７ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; method.

12. The amine compound has the formula: is a compound of During the ceremony, R １ is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; The method of claim 11.

13. The at least one silyl halide compound has the formula: is a compound of During the ceremony, X １ is F, Cl, Br or I; R ２ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ３ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ４ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; The method of claim 11.

14. The at least one silyl halide compound has the formula: is a compound of During the ceremony, X ２ is F, Cl, Br or I; R ５ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ６ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ７ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; The method of claim 11.

15. 12. The method of claim 11, wherein the molar ratio of the amine compound to the silyl halide compound is at least 1:

1.

16. 12. The method of claim 11, wherein the molar ratio of the amine compound to the silyl halide compound is at least 1:

2.

17. The contacting comprises: contacting the amine compound with the first silyl halide compound to form an intermediate; contacting the intermediate with a second silyl halide compound to obtain the precursor; The intermediate has the formula: is a compound of During the ceremony, R １ is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ２ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ３ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ４ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; The method of claim 11.

18. The contacting may comprise contacting in a solvent, the solvent being CH ２ Cl ２ , Et ２ 12. The method of claim 11, comprising at least one of O, n-hexane, EtOAc, THF, or any combination thereof.

19. 1. A method for vapor deposition comprising: obtaining a precursor, the precursor having the formula: [In the formula, R １ is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ２ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ３ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ４ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ５ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ６ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; R ７ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or benzyl; obtaining a precursor comprising a compound of vaporizing the precursor to obtain a vaporized precursor; contacting the vaporized precursor with a substrate under vapor deposition conditions to form a silicon-containing film on the substrate; A method comprising:

20. 28. The method of claim 27, wherein the vapor deposition conditions comprise plasma-enhanced atomic layer deposition conditions.

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