Sulfonates, polymers, resist compositions and patterning process
AssigneesShin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Company, Limited
InventorsYuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Haruhiko Komoriya, Satoru Miyazawa
Life of this patent
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Abstract
A sulfonate compound having formula (1) is novel wherein R1 to R3 are H, F or C1-20 alkyl or fluoroalkyl, at least one of R1 to R3 contains F. A polymer comprising units derived from the sulfonate compound is used as a base resin to formulate a resist composition which is sensitive to high-energy radiation, maintains high transparency at a wavelength of up to 200 nm, and has improved alkali dissolution contrast and plasma etching resistance
Claims19
A sulfonate compound having the following general formula (1):
- wherein R1 to R3 each are fluorine or a straight, branched or cyclic alkyl or fluorinated alkyl group of 1 to 20 carbon atoms, at least one of R1 to R3 contains fluorine, R1 and R2, R1 and R3, or R2 and R3, taken together, may form a ring, each of R1 to R3 is a straight or branched alkylene or fluorinated alkylene group of 1 to 18 carbon atoms, when they form a ring.
A polymer comprising recurring units of the following general formula (2) and having a weight average molecular weight of 1,000 to 500,000,
- wherein R1 to R3 each are fluorine or a straight, branched or cyclic alkyl or fluorinated alkyl group of 1 to 20 carbon atoms, at least one of R1 to R3 contains fluorine, R1 and R2, R1 and R3, or R2 and R3, taken together, may form a ring, each of R1 to R3 is a straight or branched alkylene or fluorinated alkylene group of 1 to 18 carbon atoms, when they form a ring.
A polymer comprising recurring units of the following general formula (2) and recurring units of at least one type selected from the following general formulae (3a) to (3f) and having a weight average molecular weight of 1,000 to 500,000,
- wherein R1 to R3 each are fluorine or a straight, branched or cyclic alkyl or fluorinated alkyl group of 1 to 20 carbon atoms, at least one of R1 to R3 contains fluorine, R1 and R2, R1 and R3or R2 and R3, taken together, may form a ring, each of R1 to R3 is a straight or branched alkylene or fluorinated alkylene group of 1 to 18 carbon atoms, when they form a ring,
- wherein R4, R5, R7, R8 and R15 each are a single bond or a straight, branched or cyclic alkylene or fluorinated alkylene group of 1 to 20 carbon atoms, R6, R9, R12 and R18 each are hydrogen or an acid labile group, R10, R11, R13, R14, R16 and R17 each are hydrogen, fluorine, a straight, branched or cyclic alkyl or fluorinated alkyl group of 1 to 20 carbon atoms, at least one of R16 and R17 contains at least one fluorine atom, R19 is a straight, branched or cyclic fluorinated alkyl group of 1 to 20 carbon atoms, “a” and “b” each are 1 or 2.
A polymer comprising recurring units of the following general formula (2) and recurring units of the following general formula (4) and having a weight average molecular weight of 1,000 to 500,000,
- wherein R1 to R3 each are fluorine or a straight, branched or cyclic alkyl or fluorinated alkyl group of 1 to 20 carbon atoms, at least one of R1 to R3 contains fluorine, R1 and R2, R1 and R3, or R2 and R3, taken together, may form a ring, each of R1 to R3 is a straight or branched alkylene or fluorinated alkylene group of 1 to 18 carbon atoms, when they form a ring,
- wherein R20 is a methylene group, oxygen atom or sulfur atom, R21 to R24 each are hydrogen, fluorine, —R25—OR26, —R25—CO2R26 or a straight, branched or cyclic alkyl or fluorinated alkyl group of 1 to 20 carbon atoms, at least one of R21 to R24 containing —R25—OR26 or —R25CO2R26, R25 is a single bond or a straight, branched or cyclic alkylene or fluorinated alkylene group of 1 to 20 carbon atoms, R26 is hydrogen, an acid labile group, adhesive group or a straight, branched or cyclic fluorinated alkyl group of 1 to 20 carbon atoms which may contain a hydrophilic group,3 and c is 0 or 1.
A polymer comprising recurring units of the following general formula (2) and recurring units of at the following general formula (5) and having a weight average molecular weight of 1,000 to 500,000,
- wherein R1to R3 each are fluorine or a straight, branched or cyclic alkyl or fluorinated alkyl group of 1 to 20 carbon atoms, at least one of R1 to R3 contains fluorine, R1 and R2, R1 and R3 or R2 and R3, taken together, may form a ring, each of R1 to R3 is a straight or branched alkylene or fluorinated alkylene group of 1 to 18 carbon atoms, when they form a ring,
- wherein R31 is hydrogen, fluorine or a straight, branched or cyclic alkyl or fluorinated alkyl group of 1 to 20 carbon atoms, R32 is a single bond or a straight, branched or cyclic alkylene or fluorinated alkylene group of 1 to 20 carbon atoms, R33 is hydrogen or an acid labile group, R34 is fluorine or a straight, branched or cyclic fluorinated alkyl group of 1 to 20 carbon atoms, d is 1 or 2, and e is an integer of 0 to 4, satisfying 1≦d+e≦5.
A polymer comprising recurring units of the following general formula (2) and recurring units of the following general formula (6) and having a weight average molecular weight of 1,000 to 500,000,
- wherein R1 to R3 each are fluorine or a straight, branched or cyclic alkyl or fluorinated alkyl group of 1 to 20 carbon atoms, at least one of R1 to R3 contains fluorine, R1 and R2, R1 and R3, or R2 and R3, taken together, may form a ring, each of R1 to R3 is a straight or branched alkylene or fluorinated alkylene group of 1 to 18 carbon atoms, when they form a ring,
- wherein R41to R43 each are hydrogen, fluorine or a straight, branched or cyclic alkyl or fluorinated alkyl group of 1 to 20 carbon atoms, and R44 is hydrogen, an acid labile group, an adhesive group or a straight, branched or cyclic fluorinated alkyl group of 1 to 20 carbon atoms which may contain a hydrophilic group such as hydroxyl.
Dependencies are inferred from the claim text.