Ester compounds, polymers, resist compositions and patterning process
AssigneeShin-Etsu Chemical Co., Ltd.
InventorsTakeshi Kinsho, Tsunehiro Nishi, Hideshi Kurihara, Mutsuo Nakashima, Koji Hasegawa, Takeru Watanabe
Life of this patent
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Abstract
A novel ester compound having an exo-form 2-alkylbicyclo[2.2.1]heptan-2-yl group as the protective group is provided as well as a polymer comprising units of the ester compound. The polymer is used as a base resin to formulate a resist composition having a higher sensitivity, resolution and etching resistance than conventional resist compositions.
Claims19
An ester compound of formula (1):
- wherein R1 is hydrogen, methyl or CH2CO2R14;
- R2 is hydrogen, methyl or CO2R14;
- R3 is a straight, branched or cyclic alkyl group of 1 to 8 carbon atoms or a substituted or unsubstituted aryl group of 6 to 20 carbon atoms;
- R4 to R13 each are hydrogen or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain a hetero atom and R4 to R13, taken together, may form a ring, and when they form a ring, they represent divalent hydrocarbon groups of 1 to 15 carbon atoms which may contain a hetero atom, or two of R4 to R13 which are attached to adjacent carbon atoms may directly bond together to form a double bond;
- R14 is a straight, branched or cyclic alkyl of 1 to 15 carbon atoms;
- and k is equal to 0 or 1, with the proviso that the formula also represents an enantiomer.
A polymer comprising units of an ester compound of formula (1a-1)
- wherein R1 is hydrogen, methyl or CH2CO2R14;
- R2 is hydrogen, methyl or CO2R14;
- R3 is a straight, branched or cyclic alkyl group of 1 to 8 carbon atoms or a substituted or unsubstituted aryl group of 6 to 20 carbon atoms;
- R4 to R13 each are hydrogen or monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain a hetero atom and R4 to R13, taken together, may form a ring, and when they form a ring, they represent divalent hydrocarbon groups of 1 to 15 carbon atoms which may contain a hetero atom, or two of R4 to R13 which are attached to adjacent carbon atoms may directly bond together to form a double bond;
- R14 is a straight, branched or cyclic alkyl of 1 to 15 carbon atoms;
- and k is equal to 0 or 1, with the proviso that the formula also represents an enantiomer,
- said polymer having a weight average molecular weight of 1,000 to 500,000.
A method for preparing a polymer comprising effecting radical polymerization, anionic polymerization or coordination polymerization between an ester compound of formula (1)
- wherein R1 is hydrogen, methyl or CH2CO2R14;
- R2 is hydrogen, methyl or CO2R14;
- R3 is a straight, branched or cyclic alkyl group of 1 to 8 carbon atoms or a substituted or unsubstituted aryl group of 6 to 20 carbon atoms;
- R4 to R13 each are hydrogen or monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain a hetero atom and R4 to R13, taken together, may form a ring, and when they form a ring, they represent divalent hydrocarbon groups of 1 to 15 carbon atoms which may contain a hetero atom, or two of R4 to R13 which are attached to adjacent carbon atoms may directly bond together to form a double bond;
- R14 is a straight, branched or cyclic alkyl of 1 to 15 carbon atoms;
- and k is equal to 0 or 1, with the proviso that the formula also represents an enantiomer
- and another compound having a carbon-to-carbon double bond.
Dependencies are inferred from the claim text.