Cyclic azastannane and cyclic oxostannane compounds and methods for preparation thereof
View Patent ↗Cyclic azastannanes and cyclic oxostannanes having formulas (I) and (II) where X is an alkoxy or dialkylamino group are a new class of cyclic compounds. These compounds have desirably high vapor pressure and high purity (containing low levels of polyalkyl contaminants after purification), and have particular interest for EUV photoresist applications. Methods for preparing these compounds are described.
1. A cyclic azastannane having formula (I):
wherein X is OR or NR′ 2 , n is an integer of 1 to 3, R is a primary, secondary, or tertiary alkyl group having 1 to about 5 carbon atoms or a substituted or unsubstituted aryl group having about 6 to about 10 carbon atoms, R′ is a primary alkyl group having 1 to about 2 carbon atoms, R″ is hydrogen, a substituted or unsubstituted primary, secondary, or tertiary, saturated or unsaturated, linear, branched, or cyclic alkyl group having 1 to about 20 carbon atoms, a substituted or unsubstituted, branched or linear aralkyl group having about 7 to about 10 carbon atoms, or a substituted or unsubstituted aryl group having about 6 to about 10 carbon atoms, and R″′ is hydrogen, a substituted or unsubstituted primary, secondary, or tertiary, saturated or unsaturated, linear, branched, or cyclic alkyl group having 1 to about 20 carbon atoms, a substituted or unsubstituted, branched or linear aralkyl group having about 7 to about 10 carbon atoms, or a substituted or unsubstituted aryl group having about 6 to about 10 carbon atoms.
2. The cyclic azastannane according to claim 1 , wherein the cyclic azastannane is N,N,N′,N′,1-pentamethyl-1,2-azastannolidine-2,2-diamine; 1-ethyl-N,N,N′,N′-tetramethyl-1,2-azastannolidine-2,2-diamine; N,N,N′,N′-tetramethyl-1-vinyl-1,2-azastannolidine-2,2-diamine, 2,2-di-tert-butoxy-1-methyl-1,2-azastannolidine; 2,2-di-tert-butoxy-1-ethyl-1,2-azastannolidine; or 2,2-di-tert-butoxy-1-vinyl-1,2-azastannolidine.
3. The cyclic azastannane according to claim 1 , having a purity of at least about 90 mol %.
4. A cyclic oxostannane having formula (II):
wherein X is OR or NR′ 2 , n is an integer of 1 to 3, R is a primary, secondary, or tertiary alkyl group having 1 to about 5 carbon atoms or a substituted or unsubstituted aryl group having about 6 to about 10 carbon atoms, R′ is a primary alkyl group having 1 to about 2 carbon atoms, and R″′ is hydrogen, a substituted or unsubstituted primary, secondary, or tertiary, saturated or unsaturated, linear, branched, or cyclic alkyl group having 1 to about 20 carbon atoms, a substituted or unsubstituted, branched or linear aralkyl group having about 7 to about 10 carbon atoms, or a substituted or unsubstituted aryl group having about 6 to about 10 carbon atoms.
5. The cyclic oxostannane according to claim 4 , wherein the cyclic oxostannane is, 2-dimethoxy-1,2-oxastannolane; 2,2-di-tert-butoxy-1,2-oxastannolane; and 2,2-di-tert-butoxy-3-methyl-1,2-oxastannolane.
6. The cyclic oxostannane according to claim 4 , having a purity of at least about 90 mol %.
7. A method for producing a cyclic azastannane according to claim 1 wherein X is OR, the method comprising reacting an aminoalkyltrialkoxystannane or aminoalkyltriaryloxystannane with a compound selected from the group consisting of HMDZ, an ammonium salt, sulfuric acid, a phosphonium salt, and an organolithium compound.
8. A method for producing a cyclic azastannane according to claim 1 wherein X is NR′ 2 , the method comprising heating an aminoalkyltrialkylaminostannane to effect cyclization.
9. A method for producing a cyclic oxostannane according to claim 4 , wherein X is OR, the method comprising reacting a trichlorostannyl alcohol with a metal alkoxide to produce a trialkoxystannyl alcohol, and heating the trialkoxystannyl alcohol to effective cyclization.
10. A method for producing a cyclic oxostannane according to claim 4 , wherein X is NR′ 2 , the method comprising reacting a (dialkylamino)trimethylsilane with a cyclic oxostannane having formula (II) wherein X is OR and R is a primary, secondary, or tertiary alkyl group having 1 to about 5 carbon atoms or a substituted or unsubstituted aryl group having about 6 to about 10 carbon atoms.