Process for preparing organotin compounds
Provided is a facile process for preparing certain organotin compounds having alkyl and alkylamino substituents. The process provides organotin precursor compounds, for example tris(dimethylamido)isopropyl tin, in a highly pure form. As such, the products of the process are particularly useful in the deposition of high-purity tin oxide films in, for example, extreme ultraviolet light (EUV) lithography techniques used in microelectronic device manufacturing.
1. A process for preparing a composition comprising a compound of Formula (I):
wherein each R is independently chosen from a C 1 -C 5 alkyl group, and R 1 is chosen from a C 1 -C 5 alkyl group, which comprises combining:
a) a compound of Formula R 1 SnX 3 , wherein X is chosen from Cl, I, and Br,
b) a compound of Formula Li(R) 2 N, and
c) a compound of Formula and R 2 NH,
wherein the compound of Formula R 2 NH is present in a molar excess over the compound of Formula R 1 SnX 3 .
2. The process of claim 1 , wherein R and R 1 are independently chosen from a C 1 -C 3 alkyl group.
3. The process of claim 1 , wherein R 1 is isopropyl and X is chloro.
4. The process of claim 1 , wherein the compound of Formula (I) is tris(dimethyl-amido)isopropyl tin; tris(diethylamido)isopropyl tin; tris(dipropylamido)isopropyl tin; tris(methylethylamido)isopropyl tin; tris(diisopropylamido)isopropyl tin; tris(di-t-butyl-amido)isopropyl tin; tris(di-n-butylamido)isopropyl tin; tris(di-sec-butylamido)isopropyl tin; tris(di-neopentylamido)isopropyl tin; tris(dimethylamido)methyl tin; tris(diethylamido)methyl tin; tris(di-n-propylamido)methyl tin; tris(methylethylamido)methyl tin; tris(diisopropylamido)methyl tin; tris(di-t-butylamido)methyl tin; tris(di-n-butylamido)methyl tin; tris(di-sec-butylamido)methyl tin; tris(di-neopentylamido)methyl tin; tris(dimethylamido)ethyl tin; tris(diethylamido)ethyl tin; tris(di-n-propylamido)ethyl tin; tris(methylethylamido)ethyl tin; tris(diisopropylamido)ethyl tin; tris(di-t-butylamido)ethyl tin; tris(di-n-butylamido)ethyl tin; tris(di-sec-butylamido)ethyl tin; tris(di-neopentylamido)ethyl tin; tris(dimethylamido)n-propyl tin; tris(diethylamido)n-propyl tin; tris(di-n-propylamido)n-propyl tin; tris(methylethylamido)n-propyl tin; tris(diisopropylamido)n-propyl tin; tris(di-t-butylamido)n-propyl tin; tris(di-n-butylamido)n-propyl tin; tris(di-sec-butylamido)n-propyl tin; tris(di-neopentylamido)n-propyl tin; tris(dimethylamido)n-butyl tin; tris(diethylamido)n-butyl tin; tris(dipropylamido)n-butyl tin; tris(methylethylamido)n-butyl tin; tris(diisopropylamido)n-butyl tin; tris(di-t-butylamido)n-butyl tin; tris(di-n-butylamido)n-butyl tin; tris(di-sec-butylamido)n-butyl tin; or tris(di-neopentylamido)n-butyl tin.
5. The process of claim 1 , wherein the compound of Formula (I) is chosen from tris(dimethylamido)isopropyl tin; tris(diethylamido)isopropyl tin; tris(dipropylamido)isopropyl tin; tris(methylethylamido)isopropyl tin; tris(diisopropylamido)isopropyl tin; tris(di-t-butylamido)isopropyl tin; tris(di-n-butylamido)isopropyl tin; tris(di-sec-butylamido)isopropyl tin; and tris(di-neopentylamido)isopropyl tin.
6. The process of claim 1 , wherein the compound of Formula Li(R) 2 N is lithium dimethylamide, the compound of Formula R 2 NH is dimethylamine, and the compound of Formula R 1 SnX 3 is isopropyl-tin trichloride.
7. The process of claim 1 , wherein the compound of Formula (I) is prepared from a compound of Formula (A):
8. The process of claim 7 , wherein the compound of Formula (A) is prepared by a reaction of the compound of Formula R 2 NH and the compound of Formula R 1 SnX 3 , wherein the compound of Formula R 2 NH is in excess of the compound of Formula R 1 SnX 3 .
9. The process of claim 7 , wherein the compound of Formula (I) is prepared by reaction of the compound of Formula (A) and the compound of Formula Li(R) 2 N.
10. The process of claim 7 , wherein the compound of Formula Li(R) 2 N is present in a molar excess of about 3 to about 3.2 molar equivalents, relative to the compound of Formula (A).
11. The process of claim 7 , wherein the compound of Formula (I) is a compound of Formula (I-a):
the compound of Formula (A) is a compound of Formula (A-a):
and the compound of Formula Li(R) 2 N is lithium dimethylamide.
12. The process of claim 7 , wherein the compound of Formula (I) is a compound of Formula (I-d):
the compound of Formula (A) is a compound of Formula (A-d):
and the compound of Formula Li(R) 2 N is lithium dimethylamide.
13. The process of claim 1 , wherein, the compound of Formula R 1 SnX 3 , wherein X is chloro or bromo and R 1 is chosen from a C 1 -C 5 alkyl group, is prepared by reacting a compound of Formula R 1 SnR 4 3 and a mono iodo chloride or bromide respectively, wherein R 4 is chosen from aryl, C 2 -C 8 alkenyl, and C 2 -C 8 alkynyl.
14. The process of claim 1 , wherein the compound of Formula R 1 SnX 3 , wherein X is chloro, bromo, or iodo and R 1 is chosen from a C 1 -C 5 alkyl group, is prepared by contacting a compound of Formula R 1 SnR 2 3 , wherein R 2 is chosen from aryl or C 2 -C 8 alkenyl, with a compound of Formula SnX 4 .