Patent Application
20240352051
The present disclosure relates to compositions comprising multi-nuclear tin compounds and related methods.
Some precursors are useful in the manufacture of microelectronic devices. The manufacture of such devices can involve use of extreme ultraviolet (EUV) lithography to form thin films.
Some embodiments relate to a method comprising: contacting a mono-substituted tin (IV) amide compound with a silanol compound to form a mixed-ligand multi-nuclear tin compound, wherein the mono-substituted tin (IV) amide compound is a compound of the formula: RSn(NR12)3, where: R is at least one of an alkyl, an alkenyl, an alkynyl, a cycloalkyl, an aryl, a silyl, a silylalkyl, an aminoalkyl, an alkoxyalkyl, an aralkyl, a fluoroalkyl, a haloalkyl, a silylated alkoxide, an ether, an amine, a halide, an imide, a cyanate, a nitrile, an alkoxide, a carboxylate, an enolate, an ester, a cyclopentadienyl, or any combination thereof; R1 is independently a hydrogen, an alkyl, a cycloalkyl, or an aryl, or each R1 is bonded to each other to form a C3-C20 N-heterocycle; wherein the silanol compound is a compound of the formula: HOSiR23, where: R2 is independently at least one of a hydrogen, a halide, an alkyl, an alkenyl, an alkynyl, a cycloalkyl, an aryl, an aralkyl, an alkaryl, or a haloalkyl.
Some embodiments relate to a composition comprising: a mixed-ligand multi-nuclear tin compound of the formula: [R2Sn2(NR12)n(OSiR23)6-n]x, where: R is at least one of an alkyl, an alkenyl, an alkynyl, a cycloalkyl, an aryl, a silyl, a silylalkyl, an aminoalkyl, an alkoxyalkyl, an aralkyl, a fluoroalkyl, a haloalkyl, a silylated alkoxide, an ether, an amine, a halide, an imide, a cyanate, a nitrile, an alkoxide, a carboxylate, an enolate, an ester, a cyclopentadienyl, or any combination thereof; R1 is independently a hydrogen, an alkyl, a cycloalkyl, or an aryl, or each R2 is bonded to each other to form a C3-C20 N-heterocycle; R2 is independently at least one of a hydrogen, a halide, an alkyl, an alkenyl, an alkynyl, a cycloalkyl, an aryl, an aralkyl, an alkaryl, or a haloalkyl; x is 1, 1.5, or 2; n is 1 to 5.
Some embodiments of the disclosure are herein described, by way of example only, with reference to the accompanying drawings. With specific reference now to the drawings in detail, it is stressed that the embodiments shown are by way of example and for purposes of illustrative discussion of embodiments of the disclosure. In this regard, the description taken with the drawings makes apparent to those skilled in the art how embodiments of the disclosure may be practiced.
Among those benefits and improvements that have been disclosed, other objects and advantages of this disclosure will become apparent from the following description taken in conjunction with the accompanying figures. Detailed embodiments of the present disclosure are disclosed herein; however, it is to be understood that the disclosed embodiments are merely illustrative of the disclosure that may be embodied in various forms. In addition, each of the examples given regarding the various embodiments of the disclosure which are intended to be illustrative, and not restrictive.
Any prior patents and publications referenced herein are incorporated by reference in their entireties.
Throughout the specification and claims, the following terms take the meanings explicitly associated herein, unless the context clearly dictates otherwise. The phrases “in one embodiment,” “in an embodiment,” and “in some embodiments” as used herein do not necessarily refer to the same embodiment(s), though it may. Furthermore, the phrases “in another embodiment” and “in some other embodiments” as used herein do not necessarily refer to a different embodiment, although it may. All embodiments of the disclosure are intended to be combinable without departing from the scope or spirit of the disclosure.
As used herein, the term “based on” is not exclusive and allows for being based on additional factors not described, unless the context clearly dictates otherwise. In addition, throughout the specification, the meaning of “a,” “an,” and “the” include plural references. The meaning of “in” includes “in” and “on.”
As used herein, the term “alkyl” refers to a hydrocarbyl having from 1 to 30 carbon atoms. The alkyl may be attached via a single bond. An alkyl having n carbon atoms may be designated as a “Cn alkyl.” For example, a “C3 alkyl” may include n-propyl and isopropyl. An alkyl having a range of carbon atoms, such as 1 to 30 carbon atoms, may be designated as a C1-C30 alkyl. 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 comprises or is selected from the group consisting of at least one of a C1-C30 alkyl, C1-C29 alkyl, C1-C28 alkyl, C1-C27 alkyl, C1-C27 alkyl, C1-C26 alkyl, C1-C25 alkyl, C1-C24 alkyl, C1-C23 alkyl, C1-C22 alkyl, C1-C21 alkyl, C1-C20 alkyl, C1-C19 alkyl, C1-C18 alkyl, C1-C17 alkyl, C1-C16 alkyl, C1-C15 alkyl, C1-C14 alkyl, C1-C13 alkyl, C1-C12 alkyl, C1-C11 alkyl, C1-C10 alkyl, a C1-C9 alkyl, a C1-C8 alkyl, a C1-C7 alkyl, a C1-C6 alkyl, a C1-C5 alkyl, a C1-C4 alkyl, a C1-C5 alkyl, a C1-C2 alkyl, a C2-C30 alkyl, a C5-C30 alkyl, a C4-C30 alkyl, a C5-C30 alkyl, a C6-C30 alkyl, a C7-C30 alkyl, a C8-C30 alkyl, a C9-C30 alkyl, a C10-C30 alkyl, a C11-C30 alkyl, a C12-C30 alkyl, a C13-C30 alkyl, a C14-C30 alkyl, a C15-C30 alkyl, a C16-C30 alkyl, a C17-C30 alkyl, a C18-C30 alkyl, a C19-C30 alkyl, a C20-C30 alkyl, a C21-C30 alkyl, a C22-C30 alkyl, a C23-C30 alkyl, a C24-C30 alkyl, a C25-C30 alkyl, a C26-C30 alkyl, a C27-C30 alkyl, a C28-C30 alkyl, a C29-C30 alkyl, a C2-C10 alkyl, a C3-C10 alkyl, a C4-C10 alkyl, a C5-C10 alkyl, a C6-C10 alkyl, a C7-C10 alkyl, a C8-C10 alkyl, a C2-C9 alkyl, a C2-C8 alkyl, a C2-C7 alkyl, a C2-C6 alkyl, a C2-C5 alkyl, a C8-C5 alkyl, or any combination thereof. In some embodiments, the alkyl comprises or is selected from the group consisting of at least one of methyl, ethyl, n-propyl, 1-methylethyl (iso-propyl), n-butyl, iso-butyl, sec-butyl, n-pentyl, 1,1-dimethylethyl (t-butyl), n-pentyl, iso-pentyl, 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 alkyls, alkenyls, alkynyls, and/or cycloalkyls.
As used herein, the term “alkenyl” refers to a hydrocarbyl having from 1 to 30 carbon atoms and at least one carbon-carbon double bond. In some embodiments, the alkenyl comprises or is selected from the group consisting of at least one of a C1-C30 alkenyl, C1-C29 alkenyl, C1-C28 alkenyl, C1-C27 alkenyl, C1-C27 alkenyl, C1-C26 alkenyl, C1-C25 alkenyl, C1-C24 alkenyl, C1-C23 alkenyl, C1-C22 alkenyl, C1-C21 alkenyl, C1-C20 alkenyl, C1-C19 alkenyl, C1-C18 alkenyl, C1-C17 alkenyl, C1-C16 alkenyl, C1-C15 alkenyl, C1-C14 alkenyl, C1-C13 alkenyl, C1-C12 alkenyl, C1-C11 alkenyl, C1-C10 alkenyl, a C1-C9 alkenyl, a C1-C8 alkenyl, a C1-C7 alkenyl, a C1-C6 alkenyl, a C1-C5 alkenyl, a C1-C4 alkenyl, a C1-C3 alkenyl, a C1-C2 alkenyl, a C2-C30 alkenyl, a C3-C30 alkenyl, a C4-C30 alkenyl, a C5-C30 alkenyl, a C6-C30 alkenyl, a C7-C30 alkenyl, a C8-C30 alkenyl, a C9-C30 alkenyl, a C10-C30 alkenyl, a C11-C30 alkenyl, a C12-C30 alkenyl, a C13-C30 alkenyl, a C14-C30 alkenyl, a C15-C30 alkenyl, a C16-C30 alkenyl, a C17-C30 alkenyl, a C18-C30 alkenyl, a C19-C30 alkenyl, a C20-C30 alkenyl, a C21-C30 alkenyl, a C22-C30 alkenyl, a C23-C30 alkenyl, a C24-C30 alkenyl, a C25-C30 alkenyl, a C26-C30 alkenyl, a C27-C30 alkenyl, a C28-C30 alkenyl, a C29-C30 alkenyl, a C2-C10 alkenyl, a C5-C10 alkenyl, a C4-C10 alkenyl, a C5-C10 alkenyl, a C6-C10 alkenyl, a C7-C10 alkenyl, a C8-C10 alkenyl, a C2-C9 alkenyl, a C2-C8 alkenyl, a C2-C7 alkenyl, a C2-C6 alkenyl, a C2-C5 alkenyl, a C3-C5 alkenyl, or any combination thereof. Examples of alkenyl groups include, without limitation, at least one of 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, 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.
As used herein, the term “alkynyl” refers to a hydrocarbyl having from 1 to 30 carbon atoms and at least one carbon-carbon triple bond. In some embodiments, the alkynyl comprises or is selected from the group consisting of at least one of a C1-C30 alkynyl, C1-C29 alkynyl, C1-C28 alkynyl, C1-C27 alkynyl, C1-C27 alkynyl, C1-C26 alkynyl, C1-C25 alkynyl, C1-C24 alkynyl, C1-C23 alkynyl, C1-C22 alkynyl, C1-C21 alkynyl, C1-C20 alkynyl, C1-C19 alkynyl, C1-C18 alkynyl, C1-C17 alkynyl, C1-C16 alkynyl, C1-C15 alkynyl, C1-C14 alkynyl, C1-C13 alkynyl, C1-C12 alkynyl, C1-C11 alkynyl, C1-C10 alkynyl, a C1-C9 alkynyl, a C1-C8 alkynyl, a C1-C7 alkynyl, a C1-C6 alkynyl, a C1-C5 alkynyl, a C1-C4 alkynyl, a C1-C3 alkynyl, a C1-C2 alkynyl, a C2-C30 alkynyl, a C3-C30 alkynyl, a C4-C30 alkynyl, a C5-C30 alkynyl, a C6-C30 alkynyl, a C7-C30 alkynyl, a C8-C30 alkynyl, a C9-C30 alkynyl, a C10-C30 alkynyl, a C11-C30 alkynyl, a C12-C30 alkynyl, a C13-C30 alkynyl, a C14-C30 alkynyl, a C15-C30 alkynyl, a C16-C30 alkynyl, a C17-C30 alkynyl, a C18-C30 alkynyl, a C19-C30 alkynyl, a C20-C30 alkynyl, a C21-C30 alkynyl, a C22-C30 alkynyl, a C23-C30 alkynyl, a C24-C30 alkynyl, a C25-C30 alkynyl, a C26-C30 alkynyl, a C27-C30 alkynyl, a C28-C30 alkynyl, a C29-C30 alkynyl, a C2-C10 alkynyl, a C3-C10 alkynyl, a C4-C10 alkynyl, a C5-C10 alkynyl, a C6-C10 alkynyl, a C7-C10 alkynyl, a C8-C10 alkynyl, a C2-C9 alkynyl, a C2-C8 alkynyl, a C2-C7 alkynyl, a C2-C6 alkynyl, a C2-C5 alkynyl, a C3-C5 alkynyl, or any combination thereof. Examples of alkynyl groups include, without limitation, at least one of ethynyl, propynyl, n-butynyl, n-pentynyl, 3-methyl-1-butynyl, n-hexynyl, methyl-pentynyl, or any combination thereof.
As used herein, the term “cycloalkyl” refers to a non-aromatic carbocyclic ring having from 3 to 8 carbon atoms in the ring. The term includes a monocyclic non-aromatic carbocyclic ring and a polycyclic non-aromatic carbocyclic ring. 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 more than one cyclic ring structure, which may be fused, bridged, spiro, or otherwise bonded ring structures. For example, two or more cycloalkyls may be fused, bridged, or fused and bridged to obtain the polycyclic non-aromatic carbocyclic ring. In some embodiments, the cycloalkyl may comprise, consist of, or consist essentially of, or may be selected from the group consisting of, at least one of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, or any combination thereof.
As used herein, the term “aryl” refers to a monocyclic or polycyclic aromatic hydrocarbon. The number of carbon atoms of the aryl may be in a range of 5 carbon atoms to 100 carbon atoms. In some embodiments, the aryl has 5 to 20 carbon atoms. For example, in some embodiments, the 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 more than one aromatic ring structure, which may be fused, bridged, spiro, or otherwise bonded ring structures. In some embodiments, the aryl is —C6H5.
As used herein, the term “amino” and/or “amine” refer to a functional group of formula —N(RaRb), wherein Ra and Rb are independently a hydrogen, an alkyl (as defined herein), or a silyl (as defined herein), or Ra and Rb are bonded to each other to form a C3-C20 N-heterocycle. In some embodiments, the amino may comprise an alkylamino or a dialkylamino. In some embodiments, the amino may comprise 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 the alkylaminos may include, without limitation, one or more of the following: primary alkylaminos, such as, for example and without limitation, 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 alkylaminos, such as, for example and without limitation, 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.
As used herein, the term “alkoxy” refers to a functional group of formula —ORc, wherein Rc is an alkyl (as defined herein), a silylalkyl, a cycloalkyl, or an aryl. In some embodiments, the alkoxy may comprise, consist of, or consist essentially of, or may selected from the group 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.
As used herein, the term “silyl” refers to a functional group of formula —Si(ReRfRg), where each of Re, Rf, and Rg is independently a hydrogen or an alkyl, as defined herein. In some embodiments, the silyl is a functional group of formula —SiH3. In some embodiments, the silyl is a functional group of formula —SiReH2, where Re is not hydrogen. In some embodiments, the silyl is a functional group of formula —SiReRfH, where Re and Rf are not hydrogen. In some embodiments, the silyl is a functional group of the formula —Si(ReRfRg), where Re, Rf, and Rg are not hydrogen. In some embodiments, the silyl is a functional group of formula —Si(CH3)3.
As used herein, the term “alkoxyalkyl” refers to an alkyl as defined herein, wherein at least one of the hydrogen atoms of the alkyl is replaced with an alkoxy as defined herein. In some embodiments, the term “alkoxyalkyl” refers to a functional group of formula -(alkyl) ORa, wherein the alkyl is defined above and wherein the Ra is defined above. In some embodiments, the alkoxyalkyl is a functional group of formula —(CH2)nORa, where n is 1 to 10 and Ra is defined above. In some embodiments, the alkoxyalkyl is a functional group of the formula —CH2CH2OCH3.
As used herein, the term “aralkyl” refers to an alkyl as defined herein, wherein 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), wherein the alkyl is defined herein and the aryl is defined herein. In some embodiments, the aralkyl is —CH2 (C6H5).
As used herein, the term “aminoalkyl” refers to an alkyl as defined herein, wherein at least one of the hydrogen atoms of the alkyl is replaced with an amino as defined herein. In some embodiments, the term “aminoalkyl” refers to a functional group of formula -(alkyl) N(RbRcRd), wherein the alkyl is defined above and wherein Rb, Rc, and Rd are defined above. In some embodiments, the aminoalkyl is —CH2N(CH3)2. In some embodiments, the aminoalkyl is —(CH2) 3N(CH3)2. In some embodiments, the aminoalkyl is aminomethyl (—CH2NH2). In some embodiments, the aminoalkyl is N,N-dimethylaminoethyl (—CH2CH2N(CH3)2). In some embodiments, the aminoalkyl is 3-(N-cyclopropylamino) propyl (—CH2CH2CH2NH—Pr).
As used herein, the term “silylalkyl” refers to an alkyl as defined herein, wherein at least one of the hydrogen atoms of the alkyl is replaced with a silyl as defined herein. In some embodiments, the term “silylalkyl” refers to a functional group of formula -(alkyl)Si(ReRfRg), wherein the alkyl is defined above and wherein Re, Rf, and Rg are defined above. In some embodiments, the silylalky is a functional group of formula —(CH2)mSi(ReRfRg), where m is 1 to 10 and where Re, Rf, and Rg are defined above. In some embodiments, the silylalkyl is a functional group of formula —CH2Si(CH3)3.
As used herein, the term “haloalkyl” refers to an alkyl as defined here, wherein at least one of the hydrogen atoms of the alkyl is replaced with a halide as defined herein. In some embodiments, the haloalkyl comprises a fluoroalkyl. In some embodiments, the fluoroalkyl comprises at least one of —CH2CF3, —CH(CF3)2, —CH2F, —CH2CH2F, —CF3, —CF2CF3, or any combination thereof.
As used herein, the term “halide” refers to a —Cl, —Br, —I, or —F.
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 a lithium cation, a sodium cation, a potassium cation, a rubidium cation, a cesium cation, a francium cation, a beryllium cation, a magnesium cation, a calcium cation, a strontium cation, a barium cation, a radium cation, a scandium cation, a titanium cation, a vanadium cation, a chromium cation, a manganese cation, an iron cation, a cobalt cation, a nickel cation, a copper cation, a zinc cation, a yttrium cation, a zirconium cation, a niobium cation, a molybdenum cation, a technetium cation, a ruthenium cation, a rhodium cation, a palladium cation, a silver cation, a cadmium cation, a hafnium cation, a tantalum cation, a tungsten cation, a rhenium cation, an osmium cation, an iridium cation, a platinum cation, a gold cation, a mercury cation, an aluminum cation, a gallium cation, an indium cation, tin cation, a thallium cation, a lead cation, a bismuth cation, or a polonium cation. The charge(s) of the metal cations are known and, for simplicity, thus are not repeated here; however, it will be appreciated that the metal cations can have any known charge. For example, in some embodiments, the metal cation comprises Li+, Na+, K+, Rb+, Cs+, Mg2+, Ca2+, Sr2+, Ba2+, Zn2+, Sn2+, or Sn4+. In some embodiments, the metal cation is Sn2+. In some embodiments, the metal cation is Sn4+.
Some embodiments relate to precursors and related methods. At least some of these embodiments relate to precursors useful in the fabrication of microelectronic devices, including semiconductor devices, and the like. For example, the precursors can be used to form silicon-containing films by one or more deposition processes. Examples of deposition processes include, without limitation, at least one of a chemical vapor deposition (CVD) process, a digital or pulsed chemical vapor deposition process, a plasma-enhanced cyclical 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.
At step 102, the method 100 comprises obtaining a mono-substituted tin (IV) amide compound. In some embodiments, the mono-substituted tin (IV) amide compound is a compound of the formula:
RSn(NR12)3,
In some embodiments, R is at least one of—CH2CF3, —CH(CF3)2, —CH2F, —CH2CH2F, —CF3, —CF2CF3, or any combination thereof. In some embodiments, R is at least one of—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, —Si(CH3)3, or any combination thereof.
In some embodiments, R1 is independently at least one of a hydrogen, a methyl, an ethyl, an isopropyl, a tert-butyl, an n-butyl, a phenyl, or any combination thereof.
In some embodiments, the mono-substituted tin (IV) amide compound comprises iPrSn(N(CH3)2)3.
At step 104, the method 100 comprises obtaining a silanol compound. In some embodiments, the silanol compound is a compound of the formula:
HOSiR23
In some embodiments, the silanol compound comprises trimethylsilanol.
In some embodiments, R is isopropyl; R1 is methyl; and R2 is methyl.
At step 106, the method 100 comprises contacting a mono-substituted tin (IV) amide compound with a silanol compound to form a multi-nuclear tin compound.
In some embodiments, the contacting comprises reacting the mono-substituted tin (IV) amide compound with the silanol compound. In some embodiments, the contacting comprises mixing the mono-substituted tin (IV) amide compound and the silanol compound. In some embodiments, the contacting comprises agitating the mono-substituted tin (IV) amide compound and the silanol compound. In some embodiments, the contacting comprises adding the mono-substituted tin (IV) amide compound and the silanol compound to a reaction vessel. In some embodiments, the contacting comprises dissolving the mono-substituted tin (IV) amide compound and the silanol compound. In some embodiments, the contacting comprises combining the mono-substituted tin (IV) amide compound and the silanol compound. In some embodiments, the contacting is performed in solution.
In some embodiments, the multi-nuclear tin compound comprises a mixed-ligand multi-nuclear tin compound. In some embodiments, the mixed-ligand multi-nuclear tin compound comprises a compound of the formula:
[R2Sn2(NR12)n(OSiR23)6-n]x
In some embodiments, each R is the same. In some embodiments, at least two R is the same. In some embodiments, each R is different. In some embodiments, at least two R is different.
In some embodiments, each R1 is the same. In some embodiments, at least two R1 is the same. In some embodiments, each R1 is different. In some embodiments, at least two R1 is different.
In some embodiments, each R2 is the same. In some embodiments, at least two R2 is the same. In some embodiments, each R2 is different. In some embodiments, at least two R2 is different.
In some embodiments, the mixed-ligand multi-nuclear tin compound is a compound of the formula:
In some embodiments, the mixed-ligand multi-nuclear tin compound is a compound of the formula:
Some embodiments relate to a composition comprising a multi-nuclear tin compound. In some embodiments, the multi-nuclear tin compound comprises a mixed-ligand multi-nuclear tin compound. In some embodiments, the mixed-ligand multi-nuclear tin compound comprises a compound of the formula:
[R2Sn2(NR12)n(OSiR23)6-n]x
In some embodiments, each R is the same. In some embodiments, at least two R is the same. In some embodiments, each R is different. In some embodiments, at least two R is different.
In some embodiments, each R1 is the same. In some embodiments, at least two R1 is the same. In some embodiments, each R1 is different. In some embodiments, at least two R1 is different.
In some embodiments, each R2 is the same. In some embodiments, at least two R2 is the same. In some embodiments, each R2 is different. In some embodiments, at least two R2 is different.
In some embodiments, the mixed-ligand multi-nuclear tin compound is a compound of the formula:
In some embodiments, the mixed-ligand multi-nuclear tin compound comprises a compound of the formula:
In some embodiments, a purity of the mixed-ligand multi-nuclear tin compound is at least 99.9%. In some embodiments, a purity of the mixed-ligand multi-nuclear tin 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, a purity of the mixed-ligand multi-nuclear tin compound is 70% to 95%, 75% to 95%, 80% to 95%, 85% to 95%, 90% to 95%, 70% to 90%, 70% to 85%, 70% to 80%, 70% to 75%, or any range or subrange between 70% and 95%. In some embodiments, a purity of the mixed-ligand multi-nuclear tin compound is 95% to 99.9999%, 95% to 99.999%, 95% to 99.99%, 95% to 99.9%, 95% to 99%, 95% to 98%, 95% to 97%, 95% to 96%, 96% to 99.9999%, 97% to 99.9999%, 98% to 99.9999%, 99% to 99.9999%, 99.9% to 99.9999%, 99.99% to 99.9999%, 99.999% to 99.9999%, or any range or subrange between 95% to 99.9999%.
iPrSn(N(CH3)2)3 (5.0 g, 17.0 mmol) (CAS #1913978-89-8) was placed in a 40 mL amber vial equipped with a magnetic stir bar and diluted with 20 mL of hexanes. The addition of a trimethylsilanol (CAS #1066-40-6) hexanes solution (4.64 g, 51.5 mmol, in 10 mL of hexanes) to the stirred tin amide solution over the course of 5 minutes resulted in an exotherm. Upon complete addition the colorless solution and was stirred for 12 hours, whereby the volatiles were removed under reduced pressure to yield the product as a brilliant white microcrystalline solid, mass: 6.68 g, yield: 91.6%. Purity: 99.96% by 1H-NMR. Melting point: (63.5° C. by DSC). Crystals suitable for X-ray crystallography were grown from the slow evaporation of a concentrated hexanes solution. 1H{13C}-NMR (400 MHZ, C6D6, 298K): 0.28 (s, 45H); 1.22 (d, 12H); 1.74 (sept, 2H); 2.63 (s, 6H) ppm; 13C{1H}-NMR (100 MHZ, C6D6, 298K): 3.68; 20.10; 28.11; 42.63 ppm; 119Sn{1H}-NMR (149 MHZ, C6D6, 298K): −310.37 ppm. 29Si{1H}-NMR (79 MHZ, C6D6, 298K): 8.58 ppm.
Various Aspects are described below. It is to be understood that any one or more of the features recited in the following Aspect(s) can be combined with any one or more other Aspect(s).
Aspect 1. A method comprising:
RSn(NR12)3,
HOSiR23
Aspect 2. The method according to Aspect 1, wherein R comprises at least one of —CH2CF3, —CH(CF3)2, —CH2F, —CH2CH2F, —CF3, —CF2CF3, or any combination thereof.
Aspect 3. The method according to any one of Aspects 1-2, wherein R comprises at least one of —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, —Si(CH3)3, or any combination thereof.
Aspect 4. The method according to any one of Aspects 1-3, wherein R1 is independently a hydrogen, a methyl, an ethyl, an isopropyl, a tert-butyl, an n-butyl, or a phenyl.
Aspect 5. The method according to any one of Aspects 1-4, wherein:
Aspect 6. The method according to any one of Aspects 1-5, wherein the mono-substituted tin (IV) amide compound comprises iPrSn(N(CH3)2)3.
Aspect 7. The method according to Aspect 6, wherein the silanol compound comprises trimethylsilanol.
Aspect 8. The method according to any one of Aspects 1-7, wherein the mixed-ligand multi-nuclear tin compound is a compound of the formula:
[R2Sn2(NR12)n(OSiR23)6-n]x
Aspect 9. The method according to any one of Aspects 1-8, wherein the mixed-ligand multi-nuclear tin compound is a compound of the formula:
Aspect 10. The method according to any one of Aspects 1-9, wherein R comprises at least one of —CH2CF3, —CH(CF3)2, —CH2F, —CH2CH2F, —CF3, —CF2CF3, or any combination thereof.
Aspect 11. The method according to any one of Aspects 1-10, wherein R comprises at least one of —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, —Si(CH3)3, or any combination thereof.
Aspect 12. The method according to any one of Aspects 1-11, wherein R2 is independently a hydrogen, a methyl, an ethyl, an isopropyl, a tert-butyl, an n-butyl, or a phenyl.
Aspect 13. The method according to any one of Aspects 1-12, wherein the mixed-ligand multi-nuclear tin compound is a compound of the formula:
Aspect 14. A composition comprising:
[R2Sn2(NR12)n(OSiR23)6-n]x
Aspect 15. The composition according to Aspect 14, wherein the mixed-ligand multi-nuclear tin compound is a compound of the formula:
Aspect 16. The composition according to any one of Aspects 14-15, wherein R comprises at least one of —CH2CF3, —CH(CF3)2, —CH2F, —CH2CH2F, —CF3, —CF2CF3, or any combination thereof.
Aspect 17. The method according to any one of Aspects 14-16, wherein R comprises at least one of —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, —Si(CH3)3, or any combination thereof.
Aspect 18. The composition according to any one of Aspects 14-17, wherein R2 is independently a hydrogen, a methyl, an ethyl, an isopropyl, a tert-butyl, an n-butyl, or a phenyl.
Aspect 19. The composition according to any one of Aspects 14-18, wherein the mixed-ligand multi-nuclear tin compound comprises a compound of the formula:
Aspect 20. The composition according to any one of Aspects 14-19, wherein a purity of the mixed-ligand multi-nuclear tin compound is at least 99.9%.
It is to be understood that changes may be made in detail, especially in matters of the construction materials employed and the shape, size, and arrangement of parts without departing from the scope of the present disclosure. This Specification and the embodiments described are examples, with the true scope and spirit of the disclosure being indicated by the claims that follow.
This application claims the benefit under 35 USC 119 of U.S. Provisional Patent Application No. 63/460,663, filed Apr. 20, 2023, the disclosure of which is hereby incorporated herein by reference in its entirety.
| Number | Date | Country | |
|---|---|---|---|
| 63460663 | Apr 2023 | US |
