Polymerizable fluorinated ester compounds and their preparing processes
AssigneeShin-Etsu Chemical Co., Ltd.
InventorsTakeshi Kinsho, Takeru Watanabe
Life of this patent
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Abstract
Polymerizable fluorinated ester compounds having formulae (1) and (2) are novel wherein R1 is H, methyl or trifluoromethyl, R2 and R3 are H or a monovalent hydrocarbon group, R2 and R3 may form a ring, R4 is H, OH or a monovalent hydrocarbon group, and R5 is an acid labile group. They are useful as monomers to produce polymers for the manufacture of radiation-sensitive resist compositions which have high transparency to radiation having a wavelength of up to 500 nm and exhibit good development properties due to the presence of phenol-like acidic hydroxyl groups
Claims5
A polymerizable fluorinated ester compound having the general formula (1) or (2):
- wherein R1 is hydrogen, methyl or trifluoromethyl, R2 and R3 are each independently hydrogen or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom, a pair of R2 and R3 may bond together to form a ring with the carbon atom to which they are bonded, and each of R2 and R3 is a divalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom when they form a ring, R4 is hydrogen, hydroxyl, or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom, and R5 is an acid labile group.
A process for preparing a polymerizable fluorinated ester compound having the general formula (1), comprising the steps of
- reacting a ketoalcohol compound having the general formula (3) with a compound of the general formula:
- R4—Z to form a diol compound having the general formula (4), and acylating the diol compound to form a polymerizable fluorinated ester compound having the general formula (1):
- wherein R1 is hydrogen, methyl or trifluoromethyl, R2 and R3 are each independently hydrogen or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom, a pair of R2 and R3 may bond together to form a ring with the carbon atom to which they are bonded, and each of R2 and R3 is a divalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom when they form a ring, R4 is hydrogen, hydroxyl, or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom, and Z is such a monovalent group that R4—Z provides a R4 anion equivalent.
A process for preparing a polymerizable fluorinated ester compound having the general formula (1), comprising the steps of
- reacting a ketoalcohol compound having the general formula (3) with a compound of the general formula:
- R4—Z to form a diol compound having the general formula (4),
- protecting the diol compound to form an alcohol compound having the general formula (5),
- acylating the alcohol compound to form a protected polymerizable fluorinated ester compound having the general formula (6), and
- deprotecting the compound of formula (6) into a polymerizable fluorinated ester compound having the general formula (1):
- wherein R1 is hydrogen, methyl or trifluoromethyl, R2 and R3 are each independently hydrogen or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom, a pair of R2 and R3 may bond together to form a ring with the carbon atom to which they are bonded, and each of R2 and R3 is a divalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom when they form a ring, R4 is hydrogen, hydroxyl, or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom, R6 is a protective group, and Z is such a monovalent group that R4—Z provides a R4 anion equivalent.
A process for preparing a polymerizable fluorinated ester compound having the general formula (2), comprising the steps of
- reacting a ketoalcohol compound having the general formula (3) with a compound of the general formula:
- R4—Z to form a diol compound having the general formula (4),
- protecting the diol compound with an acid labile group to form an alcohol compound having the general formula (7), and
- acylating the alcohol compound to form a polymerizable fluorinated ester compound having the general formula (2):
- wherein R1 is hydrogen, methyl or trifluoromethyl, R2 and R3 are each independently hydrogen or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom, a pair of R2 and R3 may bond together to form a ring with the carbon atom to which they are bonded, and each of R2 and R3 is a divalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom when they form a ring, R4 is hydrogen, hydroxyl, or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom, R5 is an acid labile group, and Z is such a monovalent group that R4—Z provides a R4 anion equivalent.
A process for preparing a polymerizable fluorinated ester compound having the general formula (2), comprising the step of protecting a polymerizable fluorinated ester compound having the general formula (1) with an acid labile group to form a polymerizable fluorinated ester compound having the general formula (2):
- wherein R1 is hydrogen, methyl or trifluoromethyl, R2 and R3 are each independently hydrogen or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom, a pair of R2 and R3 may bond together to form a ring with the carbon atom to which they are bonded, and each of R2 and R3 is a divalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom when they form a ring, R4 is hydrogen, hydroxyl, or a monovalent hydrocarbon group of 1 to 15 carbon atoms which may contain at least one hetero atom, and R5 is an acid labile group.
Dependencies are inferred from the claim text.