Compound, fluorine-containing polymer, radiation-sensitive resin composition and method for producing compound
A compound has a following general formula (1). R 0 represents an (n+1)-valent linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, or the like. R 1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group. R 2 represents a single bond or the like. R 3 represent a linear or branched alkyl group having 1 to 4 carbon atoms or the like. X represents a linear or branched fluoroalkylene group having 1 to 10 carbon atoms, and n is an integer from 1 to 5.
1. A compound having a general formula (1),
wherein
n is an integer from 2 to 5,
R 0 represents an (n+1)-valent linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, or an (n+1)-valent alicyclic hydrocarbon group having 3 to 20 carbon atoms,
R 1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group,
R 2 represents a single bond, a methylene group, an ethylene group, a 1-methylethylene group, a 2-methylethylene group, or a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms,
each R 2 is a same as or different from each other,
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, or
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, and two of R 3 groups bond to form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms together with the carbon atom bonded to the two of R 3 groups,
X represents a linear or branched fluoroalkylene group having 1 to 10 carbon atoms, and
each X is a same as or different from each other.
2. The compound according to claim 1 , the compound being shown by a general formula (1a),
wherein
n is an integer from 2 to 5,
R 1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group,
R 2 represents a single bond, a methylene group, an ethylene group, a 1-methylethylene group, a 2-methylethylene group, or a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms,
each R 2 is a same as or different from each other,
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, or
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, and two of R 3 groups bond to form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms together with the carbon atom bonded to the two of R 3 groups,
X represents a linear or branched fluoroalkylene group having 1 to 10 carbon atoms, and
each X is a same as or different from each other.
3. A compound having a general formula (1),
wherein
n is 2,
R 0 represents an (n+1)-valent linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, an (n+1)-valent alicyclic hydrocarbon group having 3 to 20 carbon atoms, or an (n+1)-valent aromatic hydrocarbon group having 6 to 20 carbon atoms,
R 1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group,
R 2 represents a single bond, a methylene group, an ethylene group, a 1-methylethylene group, a 2-methylethylene group, or a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms,
each R 2 is a same as or different from each other,
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, or
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, and two of R 3 groups bond to form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms together with the carbon atom bonded to the two of R 3 groups,
X represents a linear or branched fluoroalkylene group having 1 to 10 carbon atoms, and
each X is a same as or different from each other.
4. The compound according to claim 3 , the compound being shown by a general formula (1-2),
wherein
R 1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group,
each R 2 independently represents a single bond, a methylene group, an ethylene group, a 1-methylethylene group, a 2-methylethylene group, or a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms,
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, or
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, and two of R 3 groups bond to form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms together with the carbon atom bonded to the two of R 3 groups, and
each X independently represents a linear or branched fluoroalkylene group having 1 to 10 carbon atoms.
5. A fluorine-containing polymer comprising a repeating unit (1) derived from the compound according to claim 1 .
6. A fluorine-containing polymer comprising a repeating unit shown by a general formula (I),
wherein
n is an integer from 2 to 5,
R 0 represents an (n+1)-valent linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, or an (n+1)-valent alicyclic hydrocarbon group having 3 to 20 carbon atoms,
R 1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group,
R 2 represents a single bond, a methylene group, an ethylene group, a 1-methylethylene group, a 2-methylethylene group, or a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms,
each R 2 is a same as or different from each other,
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, or
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, and two of R 3 groups bond to form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms together with the carbon atom bonded to the two of R 3 groups,
X represents a linear or branched fluoroalkylene group having 1 to 10 carbon atoms, and
each X is a same as or different from each other.
7. The fluorine-containing polymer according to claim 6 , wherein the repeating unit shown by the general formula (I) is a repeating unit shown by a general formula (Ia),
wherein
n is an integer from 2 to 5,
R 1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group,
R 2 represents a single bond, a methylene group, an ethylene group, a 1-methylethylene group, a 2-methylethylene group, or a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms,
each R 2 is a same as or different from each other,
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, or
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, and two of R 3 groups bond to form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms together with the carbon atom bonded to the two of R 3 groups,
X represents a linear or branched fluoroalkylene group having 1 to 10 carbon atoms, and
each X is a same as or different from each other.
8. The fluorine-containing polymer according to claim 7 , wherein the repeating unit shown by the general formula (Ia) is a repeating unit shown by a general formula (I-2),
wherein
R 1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group,
each R 2 independently represents a single bond, a methylene group, an ethylene group, a 1-methylethylene group, a 2-methylethylene group, or a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms,
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, or
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, and two of R 3 groups bond to form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms together with the carbon atom bonded to the two of R 3 groups, and
each X independently represents a linear or branched fluoroalkylene group having 1 to 10 carbon atoms.
9. A radiation-sensitive resin composition comprising:
(A) the fluorine-containing polymer according to claim 5 , and
(B) an acid-labile group-containing polymer, the acid-labile group-containing polymer excluding the fluorine-containing polymer (A).
10. The radiation-sensitive resin composition according to claim 9 , wherein a content of the fluorine-containing polymer (A) in the composition is 0.1 to 40 parts by mass based on 100 parts by mass of the acid-labile group-containing polymer (B).
11. A method of producing a compound comprising reacting a compound shown by a general formula (1-0) with a compound shown by a general formula (0),
wherein
n is an integer from 2 to 5,
R 0 represents an (n+1)-valent linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, or an (n+1)-valent alicyclic hydrocarbon group having 3 to 20 carbon atoms,
R 1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group,
R 2 represents a single bond, a methylene group, an ethylene group, a 1-methylethylene group, a 2-methylethylene group, or a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms,
each R 2 is a same as or different from each other,
X represents a linear or branched fluoroalkylene group having 1 to 10 carbon atoms, and
each X is a same as or different from each other,
and wherein
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, or
each R 3 independently represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a linear or branched alkyl group having 1 to 4 carbon atoms, and two of R 3 groups bond to form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms together with the carbon atom bonded to the two of R 3 groups.