Compositions and related methods for extreme ultraviolet lithography

Abstract

Mono-substituted tin silanolate compounds and related methods are provided. The methods include contacting a mono-substituted tin(IV) compound with a silanolate reactant to form the mono-substituted tin silanolate compound. The compositions include the mono-substituted tin silanolate compound.

Description

[Technical Field]

[0001] The present disclosure relates to compositions useful in extreme ultraviolet (EUV) lithography and related applications, as well as related methods. [Background technology]

[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 are represented by Formula I:A n M(X) 4-n With respect to compounds of formula (I), M is Sn; n is 0, 1, 2, 3, or 4; and A is alkyl, alkenyl, alkynyl, carboxylate, enolate, ester, imide, alkoxide, cyclopentadienyl, ether, nitrile, cyano, isocyanate, or a combination thereof.

[0004] Some embodiments are methods comprising contacting a mono-substituted tin(IV) compound with a silanolate reactant to form a mono-substituted tin silanolate compound; the mono-substituted tin(IV) compound has the formula: RSnQ3, where R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or or any combination thereof; Q is independently at least one of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, silanolate, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; and the silanolate reactant comprises a compound of the formula: M(OSiR 2 3) n wherein M is an alkali metal cation, alkaline earth metal cation, transition metal cation, or post-transition metal cation; R 2 is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, or haloalkyl; and n is 1-4.

[0005] Some embodiments provide a composition comprising a compound of the formula: RSn(OSiR 23)3, wherein R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; and R 2 is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, or haloalkyl)

[0006] Some embodiments of the present disclosure are described herein, by way of example only, with reference to the accompanying drawings. Referring now in detail and specifically to the drawings, it is emphasized that the illustrated embodiments are by way of example and for illustrative purposes of illustrating embodiments of the present disclosure. In this regard, the description made with the drawings will make apparent to those skilled in the art how embodiments of the present disclosure may be practiced. [Brief explanation of the drawings]

[0007] [Figure 1] 1 is a flowchart of a method for producing a mono-substituted tin silanolate compound, according to some embodiments. [Figure 2] 1 shows a schematic cross-sectional view of a non-limiting embodiment of an ampoule, according to some embodiments. [Figure 3] 1 is a thermogravimetric analysis (TGA) of iPrSn(OSi(CH3)3)3, according to some embodiments. [Figure 4] 1 is a thermogravimetric analysis (TGA) of vinylSn(OSi(CH3)3)3, according to some embodiments. DETAILED DESCRIPTION OF THE INVENTION

[0008] Among these disclosed benefits and improvements, 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, each example given with respect to various embodiments of the present disclosure is intended to be illustrative and not limiting.

[0009] Any prior patents and publications referenced herein are incorporated by reference in their entirety.

[0010] Throughout the specification and claims, the following terms take on the meanings explicitly associated therewith unless the context clearly dictates otherwise. The phrases "in one embodiment," "in an embodiment," and "in some embodiments," when used herein, do not necessarily refer to the same embodiment, but may. Furthermore, the phrases "in another embodiment" and "in some other embodiments," when used herein, do not necessarily refer to different embodiments, but may refer to different embodiments. It is intended that all embodiments of the present disclosure be combinable without departing from the scope or spirit of the disclosure.

[0011] As used herein, the term "based on" is not exclusive and allows for based on additional factors not listed, unless the context clearly dictates otherwise. Furthermore, throughout this specification, the meanings of "a," "an," and "the" include plural referents. The meaning of "in" includes "in" and "on."

[0012] As used herein, the term "aliphatic hydrocarbon" refers to a monovalent or polyvalent aliphatic hydrocarbon group. This term includes, for example, but is not limited to, at least one of a monovalent alkyl group, a polyvalent alkyl group, a monovalent alkenyl group, a polyvalent alkenyl group, a monovalent alkynyl group, a polyvalent alkynyl group, or any combination thereof. The term polyvalent includes, for example, but is not limited to, at least one of a divalent group, a trivalent group, a tetravalent group, or any combination thereof, among other polyvalent groups. Non-limiting examples of aliphatic hydrocarbons include at least one of a monovalent alkyl group, a divalent alkyl group, a trivalent alkyl group, or a tetravalent alkyl group. In some embodiments, the aliphatic hydrocarbon does not contain heteroatoms. In some embodiments, the aliphatic hydrocarbon does not contain any cyclic compounds, such as, for example, but not limited to, cycloalkanes.

[0013] As used herein, the term "alkyl" refers to a hydrocarbyl having 1 to 30 carbon atoms. The alkyl may be attached through 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 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 C1-C 30 Alkyl, C1-C 29 Alkyl, C1-C 28 Alkyl, C1-C 27 Alkyl, C1-C 27 Alkyl, C1-C 26 Alkyl, C1-C 25 Alkyl, C1-C 24 Alkyl, C1-C 23 Alkyl, C1-C 22 Alkyl, C1-C 21 Alkyl, C1-C20 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 ~C 30 Alkyl, C 22 ~C 30 Alkyl, C 23 ~C 30 Alkyl, C 24 ~C 30Alkyl, 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] In some embodiments, the alkyl group includes or is 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 group includes or is 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.

[0014] 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 C1-C 30 Alkenyl, C1-C 29 Alkenyl, C1-C 28 Alkenyl, C1-C 27 Alkenyl, C1-C 27 Alkenyl, C1-C 26 Alkenyl, C1-C25 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-C9 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 30 Alkenyl, C 17 ~C 30 Alkenyl, C 18 ~C 30 Alkenyl, C 19 ~C 30 Alkenyl, C 20 ~C30 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 10 The 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.

[0015] 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 16 Alkynyl, 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, C13 ~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 ~C 30 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-hexynyl, n-pentynyl, 3-methyl-1-butynyl, 3-methyl-1-butynyl, 3-methyl-2-pent ...

[0016] As used herein, the term "cycloalkyl" refers to a non-aromatic carbocyclic group having 3 to 8 carbon atoms in 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 that 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 form a polycyclic non-aromatic carbocyclic ring. In some embodiments, a cycloalkyl may be selected from the group comprising, consisting of, consisting essentially of, or consisting of at least one of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, or any combination thereof.

[0017] 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.

[0018] As used herein, the terms “amino” and / or “amine” refer to a group of the formula —N(R a R b ) functional group, in which R a and R bare independently hydrogen, alkyl (as defined herein), or silyl (as defined herein), or R a and R b are bonded to each other and C3~C 20Forms an N-heterocycle. In some embodiments, amino can include alkylamino or dialkylamino. In some embodiments, amino can include at least one of methylamino, dimethylamino, ethylamino, diethylamino, isopropylamino, di-isopropylamino, butylamino, sec-butylamino, tert-butylamino, di-sec-butylamino, isobutylamino, di-isobutylamino, di-tert-pentylamino, ethylmethylamino, isopropyl-n-propylamino, or any combination thereof. Examples of alkylamino may include, but are not limited to, one or more of the following: primary alkylamino, such as, but not limited to, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, t-butylamino, pentylamino, 2-aminopentane, 3-aminopentane, 1-amino-2-methylbutane, 2-amino-2-methylbutane, 3-amino-2-methylbutane, 4-amino-2-methylbutane, hexylamino, 5-amino-2-methylpentane, heptylamino, octylamino, nonylamino, decylamino, undecylamino, dodecylamino, tridecylamino, tetradecylamino, pentadecylamino, hexadecylamino, heptadecylamino, and octadecylamino; and secondary Alkylamino, such as, but not limited to, dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino, diisobutylamino, di-sec-butylamino, di-t-butylamino, dipentylamino, dihexylamino, diheptylamino, dioctylamino, dinonylamino, didecylamino, methylethylamino, methylpropylamino, methylisopropylamino, methylbutylamino, methylisobutylamino, methyl-sec-butylamino, methyl-t-butylamino, methylamylamino, methylisoamylamino, ethylpropylamino, ethylisopropylamino, ethylbutylamino, ethylisobutylamino, ethyl-sec-butylamino, ethylamino, ethylisoamylamino, propylbutylamino, and propylisobutylamino.

[0019] As used herein, the term "alkoxy" refers to a group of the formula -OR c In the formula, R c is alkyl (as defined herein), silylalkyl, cycloalkyl, or aryl. In some embodiments, alkoxy can be selected from the group comprising, consisting of, consisting essentially of, or consisting of at least one of methoxy, ethoxy, methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, or any combination thereof.

[0020] 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 g are each 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 represented by 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.

[0021] 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.

[0022] 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).

[0023] 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 dis defined above. In some embodiments, an aminoalkyl is —CHN(CH). In some embodiments, an aminoalkyl is —(CH)N(CH). In some embodiments, an aminoalkyl is aminomethyl (—CHNH). In some embodiments, an aminoalkyl is N,N-dimethylaminoethyl (—CHCHN(CH)). In some embodiments, an aminoalkyl is 3-(N-cyclopropylamino)propyl (—CHCHCHNH-Pr).

[0024] 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 —CH 2 Si(CH 3 ) 3 .

[0025] As used herein, the term "haloalkyl" refers to an alkyl, as defined herein, in which at least one of the hydrogen atoms of the alkyl has been replaced with a halide, as defined herein. In some embodiments, haloalkyl includes fluoroalkyl. In some embodiments, fluoroalkyl includes -CHCF, -CH(CF), -CHF, -CHCHF, -CF 3、-CF2CF3, or any combination thereof.

[0026] As used herein, the term "halide" refers to -Cl, -Br, -I, or -F.

[0027] As used herein, the term "metal cation" refers to at least one of an alkali metal cation, an alkaline earth metal cation, a transition metal cation, a post-transition metal cation, or any combination thereof. In some embodiments, the metal cation comprises lithium cation, sodium cation, potassium cation, rubidium cation, cesium cation, francium cation, beryllium cation, magnesium cation, calcium cation, strontium cation, barium cation, radium cation, scandium cation, titanium cation, vanadium cation, chromium cation, manganese cation, iron cation, cobalt cation, nickel cation, copper cation, zinc cation, yttrium cation, zirconium cation, niobium cation, molybdenum cation, technetium cation, ruthenium cation, rhodium cation, palladium cation, silver cation, cadmium cation, hafnium cation, tantalum cation, tungsten cation, rhenium cation, osmium cation, iridium cation, platinum cation, gold cation, mercury cation, aluminum cation, gallium cation, indium cation, tin cation, thalum cation, lead cation, bismuth cation, or polonium cation. The charges of metal cations are known and will not be repeated here for brevity, although it will be understood that the metal cation can have any known charge. For example, in some embodiments, the metal cation is Li + , Na + , K. + , Rb + , Cs + , Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Zn 2+ , Sn 2+, or Sn 4+ In some embodiments, the metal cation comprises Sn 2+ In some embodiments, the metal cation is Sn 4+ is.

[0028] Some embodiments relate to precursors and related methods. At least some of these embodiments relate to precursors useful for fabricating microelectronic devices, including semiconductor devices. For example, the precursors can be used to form silicon-containing films by one or more vapor deposition methods. Examples of vapor deposition methods 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.

[0029] Some embodiments relate to compounds such as compounds used in tin oxide film growth, extreme ultraviolet lithography, plastics, or radiation sensitive film applications. The compounds include precursors that can be used to produce photoresists, for example, in processes related to the electronics industry.

[0030] Some embodiments relate to compounds for use in applications such as extreme ultraviolet lithography applications. The compounds include precursors targeted for extreme ultraviolet lithography applications, such as extreme ultraviolet hard mask applications. The compounds of the present disclosure can be used as precursors for materials used as hard mask materials in extreme ultraviolet lithography applications.

[0031] In some embodiments, the present disclosure provides a compound of formula I:A n M(X) 4-nIn some embodiments, M is Sn and n is 0, 1, 2, 3, or 4. In some embodiments, "A" is an alkyl, alkenyl, alkynyl, carboxylate, enolate, ester, imide, alkoxide, cyclopentadienyl, ether, nitrile, cyano, isocyanate, or a combination thereof.

[0032] In some embodiments, the compound is: TIFF2025528942000002.tif63170.

[0033] In some embodiments, A of formula I is an enolate. In some embodiments, the enolate is: Contains the structure of TIFF2025528942000003.tif35170.

[0034] In some embodiments, M can include a metal in solid form. For example, in some embodiments, M can include a metal in the form of a powder, particles, or tablets. In some embodiments, M is Sn.

[0035] In some embodiments, R is hydrogen or a C1-C6 alkyl group. For example, in some embodiments, the alkyl is saturated (e.g., a single bond). In some embodiments, the alkyl is unsaturated (e.g., a double bond and / or a triple bond). In some embodiments, the alkyl is linear. In some embodiments, the alkyl is branched. In some embodiments, the alkyl is substituted. In some embodiments, the alkyl is unsubstituted. In some embodiments, the alkyl can comprise, consist of, consist essentially of, or be selected from the group consisting of at least one of C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl, C1-C2 alkyl, C1 alkyl, fluorine-substituted C1-C6 alkyl, or any combination thereof.

[0036] In some embodiments, A and X are the same. For example, A and X can be ligands of the same class / family. In some embodiments, A and X are both alkyl, alkenyl, alkynyl, carboxylate, enolate, ester, imide, alkoxide, cyclopentadienyl, ether, or a combination thereof (i.e., A and X are the same combination of the preceding compounds).

[0037] In some embodiments, A in formula I is of the formula: It is a cyclopentadienyl with TIFF2025528942000004.tif36170.

[0038] In some embodiments, each R 1 ~R 5 are independently selected from hydrogen or a C1-C6 alkyl group. In some embodiments, the C1-C6 alkyl group is branched or unbranched (straight-chain). In some embodiments, the C1-C6 alkyl group is substituted or unsubstituted. For example, in some embodiments, the alkyl is saturated (e.g., a single bond). In some embodiments, the alkyl is unsaturated (e.g., a double bond and / or a triple bond). In some embodiments, the alkyl can be selected from the group comprising, consisting of, consisting essentially of, or consisting of at least one of C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl, C1-C2 alkyl, C1 alkyl, or any combination thereof.

[0039] In some embodiments, n in Formula I is 1. In some embodiments, (X) in Formula I 4-n is (NR2)3, (OR)3, (CCR)3, (CRCR2)3, or H3. In some embodiments, R is hydrogen or a C1-C6 alkyl group. In some embodiments, X is fluoride (F - ), chloride (Cl - ), bromide (Br - ), and iodide (I -In some embodiments, X in Formula I is NR2, OR, CCR, CRCR2, F, Cl, Br, I, or H. In some embodiments, R is hydrogen or a C1-C6 alkyl group. In some embodiments, R is hydrogen, a C1-C6 alkyl group, or a fluorine-substituted C1-C6 alkyl group. In some embodiments, the fluorine-substituted C1-C6 alkyl group is CH2CF3.

[0040] In some embodiments, X is a ligand. In some embodiments, the ligand is cyclopentadienyl, nitrile, or cyanide.

[0041] In some embodiments, A comprises a substituted fluorinated group. In some embodiments, the substituted fluorinated group comprises -OCH2CF3, -OCH(CF3)2, -O2CCF3, or -OC(CF3)CH2.

[0042] In some embodiments, A having a substituted fluorinated group comprises a fluorinated ether, a fluorinated carboxylate, or a fluorinated alkoxide.

[0043]

[0023] Figure 1 is a flow chart of a method 100 for producing a mono-substituted tin silanolate compound according to some embodiments. As shown in Figure 1, the method 100 for producing a mono-substituted tin silanolate compound includes one or more of the following steps: obtaining a mono-substituted tin(IV) compound in step 102, obtaining a silanolate reactant in step 104, and contacting the mono-substituted tin(IV) compound with the silanolate reactant to form the mono-substituted tin silanolate compound in step 106.

[0044] In step 102, method 100 includes providing a mono-substituted tin(IV) compound. In some embodiments, the mono-substituted tin(IV) compound has the formula: RSnQ3 and

[0045] During the ceremony,

[0046] R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; and

[0047] Q is independently at least one of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, silanolate, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof.

[0048] In some embodiments, R is -CH2CF3, -CH(CF3)2, -CH2F, -CH2CH2F, -CF3, -CF2CF3, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -C6H5, -CH2(C6H5), -CH=C at least one of H2, -C≡CCH3, -CH2C≡CH, -CH2C≡CCH3, -C(CH3)=CH2, -HC=CHCH3, -CH2CH=CH2, -CH2N(CH3)2, -(CH2)3N(CH3)2, -CH2CH2OCH3, -CH(CH2)2O, -CH2Si(CH3)3, -Si(CH3)3, or any combination thereof.

[0049] In some embodiments, R is -CHCF, -CH(CF), -CHF, -CHCHF, -CF 3、In some embodiments, R is at least one of -CF2CF3, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -CH6H5, -CH2(C6H5), -CH=CH2, -C≡CCH3, -CH2C≡CH, -CH2C≡CCH3, -C(CH3)=CH2, -HC=CHCH3, -CH2CH=CH2, -CH2N(CH3)2, -(CH2)3N(CH3)2, -CH2C2OCH3, -CH(CH2)2O, -CH2Si(CH3)3, -Si(CH3)3, or any combination thereof.

[0050] In some embodiments, Q is independently —H, —Cl, —Br, —F, —I, —NR 1 2, -OR 1 , -C≡CR 1 , -OSiR 1 3, or any combination thereof, wherein R 1 is independently at least one of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, silanolate, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof.

[0051] In some embodiments, Q is independently at least one of -Cl, -Br, -F, -I, or any combination thereof.

[0052] In some embodiments, Q is independently —H, —NR 1 2, -OR 1 , -C≡CR 1 or any combination thereof, wherein R 1is independently at least one of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, silanolate, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof.

[0053] In some embodiments, Q is -OSiR 1 3, wherein R 1 is independently at least one of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, silanolate, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof.

[0054] In some embodiments, R is -CH2CF3, -CH(CF3)2, -CH2F, -CH2CH2F, -CF3, -CF2CF3, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -C6H5, -CH2(C6H5), -CH=CH2, -C≡CCH3, -CH Q is independently at least one of -H, -Cl, -Br, -F, -I, -NR 1 2, -OR 1 , -C≡CR 1 , -OSiR 13, or any combination thereof, wherein R 1 is independently at least one of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, silanolate, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof.

[0055] In some embodiments, R and Q are different. In some embodiments, R and Q are the same. In some embodiments, R and at least one Q are different. In some embodiments, R and at least one Q are the same.

[0056] In step 104, the method 100 includes obtaining a silanolate reactant. In some embodiments, the silanolate reactant has the formula: M(OSiR 2 3) n and

[0057] During the ceremony,

[0058] M is an alkali metal cation, alkaline earth metal cation, transition metal cation, or post-transition metal cation;

[0059] R 2 is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, haloalkyl, or any combination thereof; and

[0060] n is 1 to 4.

[0061] In some embodiments, R 2 are independently hydrogen, C1 to C 12 Alkyl, C1-C12 Alkenyl, C1-C 12 at least one of alkynyl, phenyl, fluoro, chloro, bromo, iodo, or any combination thereof.

[0062] In some embodiments, R is isopropyl; Q is chloro; and M is Na. + and R 2 is methyl. In some embodiments, R is vinyl; X is chloro; and M is Na + and R 2 is methyl.

[0063] In step 106, the method 100 includes contacting a mono-substituted tin(IV) compound with a silanolate reactant to form a mono-substituted tin silanolate compound.

[0064] In some embodiments, the monosubstituted tin silanolate compound is capable of reacting with the silanolate group in a substitution reaction (e.g., where at least one of the leaving groups Q is -OSiR 2 3). In some embodiments, the contacting comprises reacting the mono-substituted tin(IV) compound with the silanolate reactant. In some embodiments, the contacting comprises mixing the mono-substituted tin(IV) compound with the silanolate reactant. In some embodiments, the contacting comprises stirring the mono-substituted tin(IV) compound with the silanolate reactant. In some embodiments, the contacting comprises adding the mono-substituted tin(IV) compound and the silanolate reactant to a reactor. In some embodiments, the contacting comprises dissolving the mono-substituted tin(IV) compound and the silanolate reactant. In some embodiments, the contacting comprises combining the mono-substituted tin(IV) compound with the silanolate reactant. In some embodiments, the contacting is performed in solution.

[0065] In some embodiments, the monosubstituted tin silanolate compound has the formula: RSn(OSiR 2 3)3 is a compound of

[0066] During the ceremony,

[0067] R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; and

[0068] R 2 is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, haloalkyl, or any combination thereof.

[0069] In some embodiments, R is -CH2CF3, -CH(CF3)2, -CH2F, -CH2CH2F, -CF3, -CF2CF3, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -C6H5, -CH2(C6H5), -CH=C at least one of H2, -C≡CCH3, -CH2C≡CH, -CH2C≡CCH3, -C(CH3)=CH2, -HC=CHCH3, -CH2CH=CH2, -CH2N(CH3)2, -(CH2)3N(CH3)2, -CH2CH2OCH3, -CH(CH2)2O, -CH2Si(CH3)3, -Si(CH3)3, or any combination thereof.

[0070] In some embodiments, R is -CHCF, -CH(CF), -CHF, -CHCHF, -CF 3、In some embodiments, R is at least one of -CF2CF3, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -CH6H5, -CH2(C6H5), -CH=CH2, -C≡CCH3, -CH2C≡CH, -CH2C≡CCH3, -C(CH3)=CH2, -HC=CHCH3, -CH2CH=CH2, -CH2N(CH3)2, -(CH2)3N(CH3)2, -CH2C2OCH3, -CH(CH2)2O, -CH2Si(CH3)3, -Si(CH3)3, or any combination thereof.

[0071] In some embodiments, R 2 are independently hydrogen, C1 to C 12 Alkyl, C1-C 12 Alkenyl, C1-C 12 at least one of alkynyl, phenyl, fluoro, chloro, bromo, iodo, or any combination thereof.

[0072] In some embodiments, the monosubstituted tin silanolate compound has the formula: The compound is TIFF2025528942000005.tif73170.

[0073] During the ceremony,

[0074] R is -CH2CF3, -CH(CF3)2, -CH2F, -CH2CH2F, -CF3, -CF2CF3, -CH3, -CH2CH3, -CH2CH2CH3, - CH(CH3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -C6H5, -CH2(C6H5), -CH=CH2, -C≡CCH3, -CH2C≡CH, -CH2C≡CCH3, -C(CH3)=CH2, -HC=CHCH3, -CH2CH=CH2, -CH2N (CH3)2, -(CH2)3N(CH3)2, -CH2CH2OCH3, -CH(CH2)2O, -CH2Si(CH3)3, or -Si(CH3)3.

[0075] In some embodiments, the monosubstituted tin silanolate compound has the formula: The compound is TIFF2025528942000006.tif85170.

[0076] In some embodiments, the monosubstituted tin silanolate compound has the formula: The compound is TIFF2025528942000007.tif85170.

[0077] Some embodiments relate to a composition. In some embodiments, the composition comprises a mono-substituted tin silanolate compound. In some embodiments, the mono-substituted tin silanolate compound has the formula: RSn(OSiR 2 3)3 is a compound of

[0078] During the ceremony,

[0079] R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; and

[0080] R 2 is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, haloalkyl, or any combination thereof.

[0081] In some embodiments, R is -CH2CF3, -CH(CF3)2, -CH2F, -CH2CH2F, -CF3, -CF2CF3, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -C6H5, -CH2(C6H5), -CH=C at least one of H2, -C≡CCH3, -CH2C≡CH, -CH2C≡CCH3, -C(CH3)=CH2, -HC=CHCH3, -CH2CH=CH2, -CH2N(CH3)2, -(CH2)3N(CH3)2, -CH2CH2OCH3, -CH(CH2)2O, -CH2Si(CH3)3, -Si(CH3)3, or any combination thereof.

[0082] In some embodiments, R is -CHCF, -CH(CF), -CHF, -CHCHF, -CF 3、 In some embodiments, R is at least one of -CF2CF3, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -CH6H5, -CH2(C6H5), -CH=CH2, -C≡CCH3, -CH2C≡CH, -CH2C≡CCH3, -C(CH3)=CH2, -HC=CHCH3, -CH2CH=CH2, -CH2N(CH3)2, -(CH2)3N(CH3)2, -CH2C2OCH3, -CH(CH2)2O, -CH2Si(CH3)3, -Si(CH3)3, or any combination thereof.

[0083] In some embodiments, R 2are independently hydrogen, C1 to C 12 Alkyl, C1-C 12 Alkenyl, C1-C 12 at least one of alkynyl, phenyl, fluoro, chloro, bromo, iodo, or any combination thereof.

[0084] In some embodiments, the monosubstituted tin silanolate compound has the formula: The compound is TIFF2025528942000008.tif73170.

[0085] During the ceremony,

[0086] R is -CH2CF3, -CH(CF3)2, -CH2F, -CH2CH2F, -CF3, -CF2CF3, -CH3, -CH2CH3, -CH2CH2CH3, - CH(CH3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -C6H5, -CH2(C6H5), -CH=CH2, -C≡CCH3, -CH2C≡CH, -CH2C≡CCH3, -C(CH3)=CH2, -HC=CHCH3, -CH2CH=CH2, -CH2N (CH3)2, -(CH2)3N(CH3)2, -CH2CH2OCH3, -CH(CH2)2O, -CH2Si(CH3)3, or -Si(CH3)3.

[0087] In some embodiments, the monosubstituted tin silanolate compound has the formula: The compound is TIFF2025528942000009.tif85170.

[0088] In some embodiments, the monosubstituted tin silanolate compound has the formula: The compound is TIFF2025528942000010.tif85170.

[0089] In some embodiments, the purity of the mono-substituted tin silanolate compound is at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 91%, at least 92%, at least 93%, at least 94%, at least 95%, at least 96%, at least 97%, at least 98%, at least 99%, at least 99.9%, at least 99.99%, at least 99.999%, at least 99.9999%, or greater. In some embodiments, the purity of the mono-substituted tin silanolate compound is 70%-95%, 75%-95%, 80%-95%, 85%-95%, 90%-95%, 70%-90%, 70%-85%, 70%-80%, 70%-75%, or any range or subrange therebetween. In some embodiments, the purity of the mono-substituted tin silanolate compound is between 95% and 99.9999%, between 95% and 99.999%, between 95% and 99.99%, between 95% and 99.9%, between 95% and 99%, between 95% and 98%, between 95% and 97%, between 95% and 96%, between 96% and 99.9999%, between 97% and 99.9999%, between 98% and 99.9999%, between 99% and 99.9999%, between 99.9% and 99.9999%, between 99.99% and 99.9999%, between 99.999% and 99.9999%, or any range or subrange therebetween.

[0090] In some embodiments, the impurity has the formula: R a Sn(OSiR 2 3) b and

[0091] During the ceremony,

[0092] a is 2, 3, or 4;

[0093] b is 0, 1, or 2; and

[0094] R and R 2 is defined above.

[0095] FIG. 2 shows a schematic cross-sectional view of a non-limiting embodiment of an ampoule 200, according to some embodiments. The ampoule 200 houses a tray assembly 202 within an inner chamber 204 of the ampoule 200. The inner chamber 204 has an inner wall surface 206. The tray assembly 202 includes trays 208, each configured to house a vaporizable precursor. In some embodiments, the vaporizable precursor comprises any one or more of the compositions disclosed herein, including compositions comprising a mono-substituted tin silanolate compound. Each of the trays 208 of the tray assembly 202 includes a portion 210 configured to contact (e.g., thermal contact, physical contact, etc.) the inner wall surface 206 of the ampoule 200. The surface-to-surface contact between the portion 210 and the inner wall surface 206 facilitates heat transfer from the ampoule 200 to each tray 208, and thus from each tray 208 to the vaporizable precursor thereon. Various fluid flow paths are defined within the interior chamber 204 of the ampoule 200, allowing fluid to flow upward, downward, or both through the ampoule 200. The ampoule 200 is shown having a generally cylindrical interior chamber. However, it will be understood that the interior chamber 204 of the ampoule may have other shapes without departing from the scope of the present disclosure. [Example]

[0096] Example 1 Synthesis of iPrSn(OSi(CH3)3)3 In a nitrogen-filled glovebox, iPrSnCl3 (20.0 g, 74.5 mmol) (CAS No. 27440-55-7) was placed in a 500 mL round-bottom flask equipped with a magnetic stir bar and diluted with 400 mL of hexanes. NaOSi(CH3)3 (26.2 g, 234 mmol) (CAS No. 18027-10-6) was added directly to the stirred solution using a conical addition funnel over 1 h, resulting in an exotherm and the appearance of a thick, white mixture. Upon completion of the addition, the flask was fitted with a reflux condenser cooled to -4 °C, and the reaction was stirred at 60 °C for 12 h. The reaction was cooled to room temperature, and the resulting thick, white mixture was filtered through a disposable polyethylene filter frit. The frit was washed with 50 mL of hexanes, and the combined organic fractions were dried under reduced pressure to give iPrSn(OSi(CH3)3)3 as a colorless liquid. Mass: 19.27 g, 60.1% yield. The product was placed in a 50 mL Schlenk flask equipped with a magnetic stir bar and placed on a Schlenk line under N working gas, equipped with a short-path distillation head equipped with a thermometer and a 50 mL collection flask. The distillation apparatus was placed under reduced pressure, the condenser was warmed to 25 °C, and the collection flask was cooled using an ice bath. The product was purified by distillation at 40-42 °C and 100-110 mTorr pressure to give iPrSn(O(Si(CH)) as a colorless liquid. Mass of distilled product: 15.11 g, distillation yield 47.3%. 1 H- and 119 The purity by Sn-NMR is >99.9%. 1 H{ 13 C}-NMR(400MHz,C6D6,298K):0.21(s,27H);1.12(d,6H);1.63(sept,1H)ppm; 13 C{ 1 H}-NMR(100MHz,C6D6,298K):3.34;19.65;26.84ppm; 119 Sn{ 1 H}-NMR(149MHz,C6D6,298K):-267.60ppm. 29 Si{ 1H}-NMR (79 MHz, CD, 298 K): 12.08 ppm. Figure 3 is a thermogravimetric analysis (TGA) of iPrSn(OSi(CH) according to some embodiments.

[0097] Example 2 Synthesis of VinylSn(OSi(CH3)3)3 In a nitrogen-filled glovebox, VinylSnCl3 (1.0 g, 3.96 mmol) was placed in a 40 mL amber vial equipped with a stir bar and dissolved in 10 mL of hexanes. NaOSi(CH3)3 (1.34 g, 12.0 mmol) (CAS No. 18027-10-6) was added over 5 minutes. An exotherm and solids were observed. The reaction mixture was then stirred overnight at 60°C. The next day, the thick reaction mixture was filtered through a disposable polyethylene (PE) frit, and the solids were washed with 5 mL of hexanes. The solvent was then removed from the filtrate and dried under reduced pressure. A clear, colorless oil was obtained, and some crystalline material was observed overnight. A minimal amount of hexanes was added to dissolve the solids, and the solution was placed in a -35°C freezer. White crystalline material was observed. The solution was decanted, and the crystalline solid was washed with 2 mL of cold hexanes and then dried under reduced pressure. VinylSn(OSi(CH3)3)3 (1.2 g, 73% yield) 119 It was recovered as a crystalline white solid (83% pure by Sn). 1 H{ 13 C}-NMR(400MHz,C6D6,298K):0.23(s,27H);5.76(2H);5.8-6.6(1H)ppm; 13 C{ 1 H}-NMR(100MHz,C6D6,298K):3.24;131.07;139.99ppm; 119 Sn{ 1 4 is a thermogravimetric analysis (TGA) of vinylSn(OSi(CH3)3)3, according to some embodiments.

[0098] Aspects

[0099] Various embodiments are described below. It should be understood that any one or more of the features described in the following embodiments can be combined with any one or more of the other embodiments. Aspect 1. Formula I:A n M(X) 4-n (I) A compound of formula (I) wherein M is Sn; n is 0, 1, 2, 3, or 4; and A is alkyl, alkenyl, alkynyl, carboxylate, enolate, ester, imide, alkoxide, cyclopentadienyl, ether, nitrile, cyano, isocyanate, or a combination thereof. Aspect 2. The compound of aspect 1, wherein A is an enolate. Aspect 3. Enolate The compound of embodiment 2, comprising the structure of TIFF2025528942000011.tif31170, wherein M is Sn. Aspect 4. The compound of aspect 3, wherein R is hydrogen or a C1-C6 alkyl group. Aspect 5. A has the following formula: The compound of embodiment 1, wherein the compound is a cyclopentadienyl having TIFF2025528942000012.tif36170. Aspect 6. Each R 1 ~R 5 are independently selected from hydrogen or a C1-C6 alkyl group. Aspect 7. The compound according to aspect 6, wherein the C1-C6 alkyl group is branched or unbranched (straight-chain). Embodiment 8. The compound according to embodiment 6, wherein the C1-C6 alkyl group is substituted or unsubstituted. Aspect 9. A compound according to any one of aspects 1 to 8, wherein n is 1. Aspect 10.(X) 4-n is (NR2)3, (OR)3, (CCR)3, (CRCR2)3, or H3. Aspect 11. The compound according to aspect 10, wherein R is hydrogen or a C1-C6 alkyl group. Embodiment 12. A compound according to any one of embodiments 1 to 11, wherein X is NR2, OR, CCR, CRCR2, F, Cl, Br, I, or H. Aspect 13. The compound according to aspect 12, wherein R is hydrogen, a C1-C6 alkyl group, or a fluorine-substituted C1-C6 alkyl group. Aspect 14. The compound according to Aspect 13, wherein the fluorine-substituted C1-C6 alkyl group is CH2CF3. Embodiment 15. The compound of any one of embodiments 1 to 11, wherein X is a ligand. Aspect 16. The compound of aspect 15, wherein the ligand is a cyclopentadienyl, a nitrile, or a cyanide. Embodiment 17. The compound of any one of embodiments 1-16, wherein A comprises a substituted fluorinated group. Embodiment 18. The compound of embodiment 17, wherein A having a substituted fluorinated group comprises —OCH 2 CF 3 , —OCH(CF 3 ) 2 , —O 2 CCF 3 , or —OC(CF 3 )CH 2 . Embodiment 19 The compound of embodiment 17, wherein A having a substituted fluorinated group comprises a fluorinated ether, a fluorinated carboxylate, or a fluorinated alkoxide. Aspect 20. The following: TIFF2025528942000013.tif63170, The compound according to embodiment 1, wherein M is Sn. 21. A method comprising: contacting a mono-substituted tin(IV) compound with a silanolate reactant to form a mono-substituted tin silanolate compound; The monosubstituted tin(IV) compound has the formula: RSnQ3 (In the formula, R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; Q is independently at least one of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, silanolate, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof. Contains the compound; The silanolate reactant has the formula: M(OSiR 2 3) n (In the formula, M is an alkali metal cation, alkaline earth metal cation, transition metal cation, or post-transition metal cation; R 2 is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, or haloalkyl; n is 1 to 4) The method of claim 1, wherein the compound is Aspect 22. R is -CH2CF3, -CH(CF3)2, -CH2F, -CH2CH2F, -CF 3、 22. The method of embodiment 21, wherein the IL-11 is at least one of: -CF2CF3, -CF4CF5, -CF5CF6, -CF6CF7, -CF7CF8, -CF8CF9, -CF9CF1, -CF1CF1, -CF1CF2, -CF1CF3 ... Embodiment 23.R is -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -C6H5, -CH2(C6H5), -CH=CH2, -C≡ CCH3, -CH2C≡CH, -CH2C≡CCH3, -C(CH3)=CH2, -HC=CHCH3, -CH2CH=CH2, -CH2N(CH3)2, -(CH2)3N(CH3)2, -CH2CH2OCH3, -CH(CH2)2O, -CH2Si(CH3) 3、 23. The method of any one of aspects 21-22, wherein the compound is at least one of: —Si(CH3)3, —Si(CH3)3, —Si(CH3)3, or any combination thereof. Embodiment 24. Q is independently -H, -Cl, -Br, -F, -I, -NR 1 2, -OR 1 , -C≡CR 1 , -OSiR 1 3, or any combination thereof; During the ceremony, R 1 is independently at least one of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, silanolate, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof. Embodiment 25. R is isopropyl; Q is chloro; M is Na + and R 2 A method according to any one of aspects 21 to 24, wherein is methyl. Aspect 26. R is vinyl; X is chloro; M is Na + and R 2 Aspect 26. The method of any one of aspects 21 to 25, wherein is methyl. Aspect 27. M is Li + , Na + , K. + , Rb + , Cs + , Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Zn 2+ , Sn 2+ , or Sn 4+ 27. The method of any one of aspects 21 to 26, wherein Aspect 28. M is Sn 4+ 28. The method of any one of aspects 21 to 27, wherein Aspect 29.R 2 are independently hydrogen, C1 to C 12 Alkyl, C1-C 12 Alkenyl, C1-C 12 Aspect 29. The method of any one of aspects 21 to 28, wherein the aryl group is at least one of alkynyl, phenyl, fluoro, chloro, bromo, iodo, or any combination thereof. Aspect 30. A monosubstituted tin silanolate compound has the formula: RSn(OSiR 2 3)3 is a compound of During the ceremony, R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; and R 2 is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, or haloalkyl. Aspect 31. The monosubstituted tin silanolate compound has the formula: The compound is TIFF2025528942000014.tif73170. During the ceremony, R is -CH2CF3, -CH(CF3)2, -CH2F, -CH2CH2F, -CF3, -CF2CF3, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH 3)2, -CH(CH3)CH2CH3, -CH2CH(CH3)2, -C(CH3)3, -(CH2)3CH3, -C6H5, -CH2(C6H5), -CH=CH2, -C 31. The method of any one of aspects 21 to 30, wherein the aryl group is ≡CCH3, -CH2C≡CH, -CH2C≡CCH3, -C(CH3)=CH2, -HC=CHCH3, -CH2CH=CH2, -CH2N(CH3)2, -(CH2)3N(CH3)2, -CH2CH2OCH3, -CH(CH2)2O, -CH2Si(CH3)3, or -Si(CH3)3. Aspect 32. The monosubstituted tin silanolate compound has the formula: The method of any one of aspects 21 to 31, wherein the compound is a compound of TIFF2025528942000015.tif85170. Aspect 33. The monosubstituted tin silanolate compound has the formula: The method of any one of aspects 21 to 32, wherein the compound is a compound of TIFF2025528942000016.tif85170. Embodiment 34. A composition comprising: formula: RSn(OSiR 2 3)3 (In the formula, R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; and R 2 is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, or haloalkyl) A composition comprising a mono-substituted tin silanolate compound of formula: Aspect 35. The monosubstituted tin silanolate compound has the formula: The compound is TIFF2025528942000017.tif73170. During the ceremony, 35. The composition of embodiment 34, wherein R is -CHCF, -CH(CF), -CHF, -CHCHF, -CF, -CFCF, -CH, -CHCH, -CHCHCH, -CH(CH), -CH(CH)CHCH, -CHCH(CH), -C(CH), -(CH)CH, -CHH, -CH(CH), -CH=CH, -C≡CCH, -CHC≡CH, -CHC≡CCH, -C(CH)=CH, -HC=CHCH, -CHCH=CH, -CHN(CH), -(CH)N(CH), -CHCHOCH, -CH(CH)O, -CHSi(CH), or -Si(CH). Aspect 36. The monosubstituted tin silanolate compound has the formula: 36. The composition of any one of aspects 34-35, wherein the composition is a compound of TIFF2025528942000018.tif85170. Aspect 37. The composition of aspect 36, wherein the purity of the mono-substituted tin silanolate compound is at least 99.9%. Aspect 38. The monosubstituted tin silanolate compound has the formula: The composition of any one of embodiments 34 to 37, wherein the compound is a silanolate compound of TIFF2025528942000019.tif85170. Embodiment 39. The composition of embodiment 38, wherein the purity of the mono-substituted tin silanolate compound is at least 80%. Embodiment 40. The composition of any one of embodiments 34-39, wherein the purity of the mono-substituted tin silanolate compound is at least 99.9%. It is to be understood that changes may be made in details, particularly with respect to the construction materials used and the shape, size and arrangement of the parts, without departing from the scope of the present disclosure. The specification and described embodiments are examples, with the true scope and spirit of the present disclosure being indicated by the appended claims.

Claims

1. 1. A method comprising: contacting a mono-substituted tin(IV) compound with a silanolate reactant to form a mono-substituted tin silanolate compound; The monosubstituted tin(IV) compound has the formula: RS.Q ３ (In the formula, R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amide, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; Q is independently at least one of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, silanolate, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amide, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof. The compound of formula (I) is The silanolate reactant has the formula: M(OSiR ２ ３ ) ｎ (In the formula, M is an alkali metal cation, alkaline earth metal cation, transition metal cation, or post-transition metal cation; R ２ is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, or haloalkyl; n is 1 to 4) The method of claim 1, wherein the compound is

2. R is -CH ２ CF ３ , -CH(CF ３ ) ２ , -CH ２ F, -CH ２ CH ２ F, -CF ３、 -CF ２ CF ３ 10. The method of claim 1, wherein the at least one of:

3. R is -CH ３ , -CH ２ CH ３ , -CH ２ CH ２ CH ３ , -CH(CH ３ ) ２ , -CH(CH ３ ) CH ２ CH ３ , -CH ２ CH (CH ３ ) ２ , -C(CH ３ ) ３ , -(CH ２ ) ３ CH ３ , -C ６ H ５ , -CH ２ (C ６ H ５ ), -CH=CH ２ , -C≡CCH ３ , -CH ２ C≡CH, -CH ２ C≡CCH ３ , -C(CH ３ ) = CH ２ , -HC=CHCH ３ , -CH ２ CH=CH ２ , -CH ２ N (CH ３ ) ２ , -(CH ２ ) ３ N (CH ３ ) ２ , -CH ２ CH ２ OCH ３ , -CH(CH ２ ) ２ O, -CH ２ Si(CH ３ ) ３、 -Si(CH ３ ) ３ 10. The method of claim 1, wherein the at least one of:

4. Q is independently —H, —Cl, —Br, —F, —I, or —NR １ ２ , -OR １ , -C≡CR １ , -OSiR １ ３ or any combination thereof; During the ceremony, R １ is independently at least one of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, silanolate, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof.

5. R is isopropyl; Q is chloro; M is Na ＋ and R ２ The method of claim 1 , wherein is methyl.

6. R is vinyl; X is chloro; M is Na ＋ and R ２ The method of claim 1 , wherein is methyl.

7. M is Li ＋ , Na ＋ , K. ＋ , Rb ＋ , Cs ＋ , Mg ２＋ , Ca ２＋ , Sr ２＋ , Ba ２＋ , Zn ２＋ , Sn ２＋ , or Sn ４＋ The method of claim 1, wherein

8. M is Sn ４＋ The method of claim 1, wherein

9. R ２ are independently hydrogen, C １ ~C １２ Alkyl, C １ ~C １２ Alkenyl, C １ ~C １２ 10. The method of claim 1, wherein the alkyl group is at least one of alkynyl, phenyl, fluoro, chloro, bromo, iodo, or any combination thereof.

10. The monosubstituted tin silanolate compound has the formula: RSn(OSiR ２ ３ ) ３ is a compound of During the ceremony, R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; and R ２ 10. The method of claim 1, wherein is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, or haloalkyl.

11. The monosubstituted tin silanolate compound has the formula: is a compound of During the ceremony, Rが、-CH ２ CF ３ 、-CH(CF ３ ) ２ 、-CH ２ F、-CH ２ CH ２ F、-CF ３ 、-CF ２ CF ３ 、-CH ２ CN、-CN、-CH ３ 、-CH ２ CH ３ 、-CH ２ CH ２ CH ３ 、-CH(CH ３ ) ２ 、-CH(CH ３ )CH ２ CH ３ 、-CH ２ CH(CH ３ ) ２ 、-C(CH ３ ) ３ 、-(CH ２ ) ３ CH ３ 、-C ６ H ５ 、-CH ２ (C ６ H ５ )、-CH=CH ２ 、-C≡CCH ３ 、-CH ２ C≡CH、-CH ２ C≡CCH ３ 、-C(CH ３ )=CH ２ HC=CHCH ３ 、-CH ２ CH=CH ２ 、-CH ２ N(CH ３ ) ２ 、-(CH ２ ) ３ N(CH ３ ) ２ 、-CH ２ CH ２ SO ３ 、-CH(CH ２ ) ２ O、-CH ２ H ３ ) ３、 or -Si(CH ３ ) ３ The method of claim 1, wherein

12. The monosubstituted tin silanolate compound has the formula: The method of claim 1, wherein the compound is

13. The monosubstituted tin silanolate compound has the formula: The method of claim 1, wherein the compound is

14. 1. A composition comprising: formula: RSn(OSiR ２ ３ ) ３ (In the formula, R is at least one of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, silyl, silylalkyl, aminoalkyl, alkoxyalkyl, aralkyl, fluoroalkyl, haloalkyl, silylated alkoxide, ether, amine, halide, imide, cyanate, nitrile, alkoxide, carboxylate, enolate, ester, cyclopentadienyl, or any combination thereof; and R ２ is independently at least one of hydrogen, halide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, alkaryl, or haloalkyl. A composition comprising a mono-substituted tin silanolate compound of formula:

15. The monosubstituted tin silanolate compound has the formula: is a compound of During the ceremony, Rが、-CH ２ CF ３ 、-CH(CF ３ ) ２ 、-CH ２ F、-CH ２ CH ２ F、-CF ３ 、-CF ２ CF ３ 、-CH ３ 、-CH ２ CH ３ 、-CH ２ CH ２ CH ３ 、-CH(CH ３ ) ２ 、-CH(CH ３ )CH ２ CH ３ 、-CH ２ CH(CH ３ ) ２ 、-C(CH ３ ) ３ 、-(CH ２ ) ３ CH ３ 、-C ６ H ５ 、-CH ２ (C ６ H ５ )、-CH=CH ２ 、-C≡CCH ３ 、-CH ２ C≡CH、-CH ２ C≡CCH ３ 、-C(CH ３ )=CH ２ HC=CHCH ３ 、-CH ２ CH=CH ２ 、-CH ２ N(CH ３ ) ２ 、-(CH ２ ) ３ N(CH ３ ) ２ 、-CH ２ CH ２ SO ３ 、-CH(CH ２ ) ２ O、-CH ２ H ３ ) ３ 、または-Si(CH ３ ) ３ 15. The composition of claim 14, wherein

16. The monosubstituted tin silanolate compound has the formula:

15. The composition of claim 14, wherein the compound is

17. 17. The composition of claim 16, wherein the purity of the mono-substituted tin silanolate compound is at least 99.9%.

18. The monosubstituted tin silanolate compound has the formula: The composition of claim 14, wherein the silanolate compound is

19. 20. The composition of claim 18, wherein the purity of the mono-substituted tin silanolate compound is at least 80%.

20. 15. The composition of claim 14, wherein the purity of the mono-substituted tin silanolate compound is at least 99.9%.

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