Deuterated organotin compounds, methods of synthesis and radiation patterning

Abstract

Organotin compounds are presented that are represented by the formula RSnL, wherein R is a deuterated hydrocarbyl group and L is a hydrolysable ligand. Two different synthesis techniques are described for synthesizing these compositions. A first method involves reacting a primary halide hydrocarbyl compound (R—X, where X is a halide atom) with an organometallic composition comprising SnLmoieties associated with metal cations M, where M is an alkali metal, alkaline earth metal, and/or pseudo-alkaline earth metal (Zn, Cd, or Hg), and L is either an amide ligand resulting in an alkali metal tin triamide compound or an acetylide ligand resulting in an alkali metal tin triacetylide, to form correspondingly a monohydrocarbyl tin triamide (RSn(NR')) or a monohydrocarbyl tin triacetylide (RSn(C═CR)). An alternative approach involves reacting a Grignard reagent RMgX with SnLin a solution comprising an organic solvent to form a monoorgano tin tralkylamide, a monoorgano tin trialkoxide, monoorgano tin tri acetylide or monoorgano tin tricarboxylate. The compositions are useful for radiation patterning, especially with EUV radiation.