Process for preparing organotin compounds
Provided is an efficient and effective process for preparing certain organotin compounds having alkyl and alkylamino substituents. The process provides the organotin compounds in a highly pure crystalline form which are particularly useful as precursors in the deposition of high-purity tin oxide films in, for example, extreme ultraviolet light (EUV) lithography techniques used in the manufacture of certain microelectronic devices.
1. A process for preparing a monoalkyl tris(dialkylamido) tin compound of Formula (I):
wherein each R is the same or different and is a C 1 -C 4 alkyl group and R 1 is a substituted or unsubstituted saturated or unsaturated linear, branched, or cyclic C 1 -C 5 group; wherein the process comprises:
contacting a compound of Formula (A)
with a compound of Formula R 1 —X, wherein X is bromo, iodo, or chloro.
2. The process of claim 1 , wherein each R is independently a methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, or sec-butyl group.
3. The process of claim 1 , wherein each R is a methyl group.
4. The process of claim 1 , wherein R 1 is a methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, sec-butyl, n-pentyl, iso-pentyl, or neopentyl group.
5. The process of claim 1 , wherein R 1 is a cyclic C 1 -C 5 group.
6. The process of claim 1 , wherein R 1 is a vinyl group or an acetylenyl group.
7. The process of claim 1 , wherein R 1 is substituted with one or more halogen groups.
8. The process of claim 1 , wherein R 1 is an alkylether group.
9. The process of claim 1 , wherein each R is a methyl group and R 1 is an isopropyl group.
10. The process of claim 1 , wherein X is iodo.
11. The process of claim 1 , wherein the process is conducted in a non-polar aprotic solvent.
12. The process of claim 1 , wherein the process further comprises preparing the compound of Formula (A) by reacting tin(II) chloride with a compound of Formula M-N(R) 2 , wherein M is sodium, lithium, and potassium.
13. The process of claim 12 , wherein the compound of Formula M-N(R) 2 is Li—N(CH 3 ) 2 .
14. The process of claim 12 , wherein the process is conducted in one reaction vessel.
15. A compound of the Formula (II):
wherein each R is the same or different and is a C 1 -C 4 alkyl group and X is iodo, bromo, and chloro, provided that wherein X is chloro, R is other than a methyl group.
16. The compound of claim 15 , wherein each R is the same or different and is a C 1 -C 4 alkyl and X is iodo and bromo.
17. The compound of claim 15 , wherein each R is a methyl group and X is iodo.
18. The compound of claim 17 in crystalline form and having the structure as set forth in FIG. 1 .