Process for preparing organotin compounds
Provided is a facile methodology for preparing certain organotin compounds having alkyl and alkylamino or alkyl and alkoxy substituents. The process provides the organotin compounds in a highly pure 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 compound of the Formula (I):
wherein each R is independently chosen from C 1 -C 5 alkyl groups, each R 1 is independently chosen from C 1 -C 5 alkyl groups, and R 2 is chosen from a vinyl group or an acetylenyl group, wherein the process comprises:
contacting a compound of the Formula (A)
with a compound of the Formula L-R 2 , wherein L is leaving group, and M is chosen from sodium, lithium, or potassium.
2. The process of claim 1 , wherein L is a halide or a substituted or unsubstituted aromatic or alkyl sulfonate.
3. The process of claim 1 , wherein L is bromo, iodo, or chloro.
4. The process of claim 1 , wherein each R and each R 1 is independently chosen from C 1 -C 3 alkyl group.
5. The process of claim 1 , wherein the compound of Formula A is prepared by reaction of a dihalostannane with a compound of the Formula (B):
6. The process of claim 5 , wherein the dihalostannane is SnCl 2 .
7. A process for preparing a compound of Formula (I):
wherein each R is independently chosen from C 1 -C 5 alkyl groups, each R 1 is independently chosen from C 1 -C 5 alkyl groups, and R 2 is chosen from hydrogen or C 1 -C 5 alkyl groups, wherein the process comprises:
contacting a compound of Formula (II):
wherein each R 3 is independently chosen from straight or branched chain C 1 -C 8 alkyl groups, a phenyl group, and substituted phenyl groups,
with a compound of Formula (R 4 ) 3 Si—N(R)(R 1 ), wherein R 4 is chosen from C 1 -C 3 alkyl groups.
8. The process of claim 7 , wherein R 3 is a substituted phenyl group selected from phenyl groups substituted one or more times with groups chosen from C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfonyl, hydroxy, cyano, nitro, halo, trihalomethyl, phenyl, phenoxy, and C 3 -C 6 cycloalkyl.
9. The process of claim 8 , wherein substituted phenyl group is a 2,6-di-t-butylphen-1-yl group or a 2,4,6-trimethylphenyl group.
10. The process of claim 7 , wherein the compound of the formula (R 4 ) 3 Si—N(R)(R 1 ) is (CH 3 ) 3 Si—N(CH 3 ) 2 .
11. The process of claim 7 , wherein the compound of Formula (II) is prepared by reacting a diahalostannane with a compound of Formula M-OR 3 , wherein M is chosen from sodium, lithium, or potassium to provide a compound of Formula (C):
wherein n is greater than or equal to 1.
12. The process of claim 11 , wherein the compound of Formula (C) is further reacted with a compound of Formula X—R 2 to provide the compound of Formula (II).
13. A compound of Formula (II):
wherein each R 3 is independently chosen from straight or branched chain C 1 -C 8 alkyl groups, a phenyl group, and substituted phenyl groups, and R 2 is chosen from hydrogen or C 1 -C 5 alkyl groups wherein R 3 is 2,6-di-t-butylphen-1-yl or 2,4,6-trimethylphenyl.