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.
Claims17
A method for synthesizing an alkene fluoroalkanol, comprising contacting (a) an olefinic reactant with (b) a fluorinated ketone, under reaction conditions and for a time period effective to allow addition of the olefinic reactant to the carbonyl carbon of the fluorinated ketone, wherein the olefinic reactant has the structure of formula (I)
- 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 wherein not more than one of R1 and R2 is H;
- and
- R3, R4, and R5 are independently selected from hydrogen, C1-C24 alkyl, and substituted C1-C24 alkyl, provided that two of R3, R4, and R5 are taken together to form a ring,
- wherein the contacting produces an alkaline fluoroalkanol that has 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 wherein not more than one of R1 and R2 is H;
- and
- R3, R4, and R5 are independently selected from hydrogen, C1-C24 alkyl, and substituted C1-C24 alkyl, provided that two of R3, R4, and R5 are taken together to form a ring;
- R6 is selected from hydrogen, C1-C24 alkyl, substituted C1-C24 alkyl, C3-C25 acylmethyl, (fluorinated C2-C24 acyl)-substituted methyl, (fluorinated C2-C24 acyl)-substituted difluoromethyl, 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
- R7 is C1-C24 alkyl or fluorinated C1-C24 alkyl, with the proviso that at least one of R6 and R7 is fluorinated.
Dependencies are inferred from the claim text.