Precursors to fluoroalkanol-containing olefin monomers, and associated methods of synthesis and use
AssigneeInternational Business Machines Corporation
InventorsGregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
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Abstract
The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted α,β-unsaturated esters. The fluoroalkanol-substituted α,β-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.
Claims20
An alkene fluoroalkanol having the structure of formula (III)
- wherein:
- R1 is selected from hydrogen, C1-C24 alkyl, substituted C1-C24 alkyl, C1-C24 alkoxy, and substituted C1-C24 alkoxy, wherein the substituted C1-C24 alkyl is not fluorinated C1-C24 hydroxyalkyl;
- R2 is selected from hydrogen, C1-C24 alkyl and substituted C1-C24 alkyl, wherein the substituted C1-C24 alkyl is not fluorinated C1-C24 hydroxyalkyl;
- R3, R4, and R5 are independently selected from hydrogen, C1-C24 alkyl, and substituted C1-C24 alkyl, provided that any two of R1, R2, R3, R4, and R5 excluding the pairing of R1 with R3 and further excluding the pairing of R2 with R3 are taken together to form a ring;
- R6A is selected from fluorinated C1-C24 alkyl and —(CO)—R, in which R is hydrogen, hydroxyl, halo, C1-C24 alkyl, substituted C1-C24 alkyl, amino, C1-C24 alkylamino, or di(C1-C24 alkyl)amino;
- and
- R7A is fluorinated C1-C24 alkyl, and further wherein when two of R1, R2, and R3 are hydrogen, then R6A and R7A are taken together to form a ring.
An alkene fluoroalkanol having the structure of formula (III)
- wherein:
- R1 is selected from hydrogen, C1-C24 alkyl, substituted C1-C24 alkyl, C1-C24 alkoxy, and substituted C1-C24 alkoxy, wherein the substituted C1-C24 alkyl is not fluorinated C1-C24 hydroxyalkyl;
- R2 is selected from hydrogen, C1-C24 alkyl and substituted C1-C24 alkyl, wherein the substituted C1-C24 alkyl is not fluorinated C1-C24 hydroxyalkyl and further provided that R1 and R2 are not both hydrogen;
- R3 is selected from C1-C24 alkyl and substituted C1-C24 alkyl;
- R4 and R5 are independently selected from hydrogen, C1-C24 alkyl, and substituted C1-C24 alkyl, and further wherein any two of R1, R2, R3, R4 and R5 are taken together to form a ring;
- R6A is selected from hydrogen, C1-C24 alkyl, substituted C1-C24 alkyl, and —(CO)—R in which R is hydrogen, hydroxyl, halo, C1-C24 alkyl, substituted C1-C24 alkyl, amino, C1-C24 alkylamino, or di(C1-C24 alkyl)amino;
- and
- R7A is C1-C24 alkyl or substituted C1-C24 alkyl, and further wherein R6A and R7A may be taken together to form a ring, with the proviso that at least one of R6A and R7A is fluorinated.
An alkene fluoroalkanol having the structure of formula (III)
- wherein:
- R1 is selected from hydrogen, C1-C24 alkyl, substituted C1-C24 alkyl, C1-C24 alkoxy, and substituted C1-C24 alkoxy, wherein the substituted C1-C24 alkyl is not fluorinated C1-C24 hydroxyalkyl;
- R2 is selected from hydrogen, C1-C24 alkyl and substituted C1-C24 alkyl, wherein the substituted C1-C24 alkyl is not fluorinated C1-C24 hydroxyalkyl;
- R3, R4, and R5 are independently selected from hydrogen, C1-C24 alkyl, and substituted C1-C24 alkyl, provided that:
- (a) R1 or R2 is taken together with R3 to form a ring;
- or (b) R4 or R5 is taken together with R3 to form a ring;
- R6A is selected from hydrogen, C1-C24 alkyl, substituted C1-C24 alkyl, and —(CO)—R, in which R is hydrogen, hydroxyl, halo, C1-C24 alkyl, substituted C1-C24 alkyl, amino, C1-C24 alkylamino, or di(C1-C24 alkyl)amino;
- and
- R7A is C1-C24 alkyl or substituted C1-C24 alkyl and further wherein R6A and R7A may be taken together to form a ring.
Dependencies are inferred from the claim text.