Polymer, radiation-sensitive composition, monomer, and method of producing compound
A polymer includes a repeating unit shown by a general formula (1). R 1 represents a hydrogen atom, a methyl group, a fluorine atom, or a trifluoromethyl group. R 2 represents a substituted or unsubstituted aryl group having 6 to 22 carbon atoms. Y represents a carbon atom. X represents —X 1 Z 1 X 2 — which is an atomic group which forms a cyclic structure including a heteroatom together with Y. Z 1 represents —O—, —S—, —CO—, —COO—, —SO—, or —SO 2 —. Each of X 1 and X 2 individually represents a single bond, a methylene group, or an alkylene group having 2 to 25 carbon atoms. Each of X 1 and X 2 is unsubstituted or substituted with a substituent, and optionally a carbon atom included in X 1 and a carbon atom included in X 2 are bonded via a divalent group.
1. A polymer comprising:
a repeating unit shown by a general formula (1),
wherein
R 1 represents a hydrogen atom, a methyl group, a fluorine atom, or a trifluoromethyl group,
R 2 represents a substituted or unsubstituted aryl group having 6 to 22 carbon atoms,
Y represents a carbon atom, and
X represents —X 1 Z 1 X 2 — which is an atomic group which forms a cyclic structure including a heteroatom together with Y, wherein
Z 1 represents —O—, —S—, —CO—, —COO—, —SO—, or —SO 2 —, and
each of X 1 and X 2 individually represents a single bond, a methylene group, or an alkylene group having 2 to 25 carbon atoms, each of X 1 and X 2 being unsubstituted or substituted with a substituent, and optionally a carbon atom included in X 1 and a carbon atom include in X 2 being bonded via a divalent group.
2. The polymer according to claim 1 , wherein the repeating unit shown by the general formula (1) is a repeating unit shown by a general formula (1-1),
wherein
n is an integer from 0 to 3,
R 1 represents a hydrogen atom, a methyl group, a fluorine atom, or a trifluoromethyl group,
R 3 represents a monovalent organic group, a hydroxyl group, or a halogen atom,
Y represents a carbon atom, and
X represents —X 1 Z 1 X 2 — which is an atomic group which forms a cyclic structure including a heteroatom together with Y, wherein
Z 1 represents —O—, —S—, —CO—, —COO—, —SO—, or —SO 2 —, and
each of X 1 and X 2 individually represents a single bond, a methylene group, or an alkylene group having 2 to 25 carbon atoms, each of X 1 and X 2 being unsubstituted or substituted with a substituent, and optionally a carbon atom included in X 1 and a carbon atom included in X 2 being bonded via a divalent group.
3. The polymer according to claim 1 , further comprising:
one of a repeating unit shown by a general formula (2), a repeating unit shown by a general formula (3), a repeating unit shown by a general formula (4), a repeating unit shown by a general formula (5), a repeating unit shown by a general formula (N), or a combination thereof,
wherein R 4 represents a hydrogen atom or a methyl group, R 5 represents a hydrogen atom or a monovalent organic group, i is an integer from 0 to 3, and j is an integer from 0 to 3, wherein 0≦i+j≦5 is satisfied,
wherein R 6 represents a hydrogen atom or a methyl group, R 7 represents a hydrogen atom or a monovalent organic group, k is an integer from 0 to 3, and l is an integer from 0 to 3, wherein 0≦k+l≦5 is satisfied,
wherein R 8 represents a hydrogen atom or a methyl group, R 9 represents a hydrogen atom or a monovalent organic group, m is an integer from 0 to 3, and n is an integer from 0 to 3, wherein 0≦m+n≦5 is satisfied,
wherein R 10 represents a hydrogen atom or a methyl group, R 11 represents a hydrogen atom or a monovalent organic group, r is an integer from 0 to 3, and s is an integer from 0 to 3,
wherein R represents a hydrogen atom or methyl group.
4. A radiation-sensitive composition comprising:
the polymer according to claim 1 , the polymer containing an acid-labile group; and
a photoacid generator.
5. The radiation-sensitive composition according to claim 4 , wherein the photoacid generator is a compound shown by a general formula (b1),
M + Z − (b1)
wherein M + represents a monovalent onium cation, and Z − represents a monovalent anion shown by a general formula (9-1) or (9-2),
wherein
each of R 14 and R 15 individually represents an alkyl group having 1 to 20 carbon atoms and being substituted with at least one fluorine atom, or R 14 and R 15 bond to each other to form a cyclic structure having 1 to 20 carbon atoms and being substituted with at least one fluorine atom, and
each of R 16 , R 17 , and R 18 individually represents an alkyl group having 1 to 20 carbon atoms and being substituted with at least one fluorine atom, or
two of R 16 , R 17 , and R 18 bond to each other to form a cyclic structure having 1 to 20 carbon atoms and being substituted with at least one fluorine atom, and the remainder of R 16 , R 17 , and R 18 represents an alkyl group having 1 to 20 carbon atoms and being substituted with at least one fluorine atom.
6. A monomer which is a compound shown bra general formula (10),
wherein
R 1 represents a hydrogen atom, a methyl group, a fluorine atom, or a trifluoromethyl group,
R 2 represents a substituted or unsubstituted aryl group having 6 to 22 carbon atoms,
Y represents a carbon atom, and
X represents —X 1 Z 1 X 2 — which is an atomic group which forms a cyclic structure including a heteroatom together with Y, wherein
Z 1 represents —O—, —S—, —CO—, —COO—, —SO—, or —SO 2 —, and
each of X 1 and X 2 individually represents a single bond, a methylene group, or an alkylene group having 2 to 25 carbon atoms, each of X 1 and X 2 being unsubstituted or substituted with a substituent, and optionally a carbon atom included in X 1 and a carbon atom included in X 2 being bonded via a divalent group.
7. A method of producing a compound shown by a general formula (10), comprising:
providing a first compound shown by a formula (AA) and a second compound, the second compound having a partial structure shown by a formula (BB); and
reacting the first compound and the second compound to replace Y 1 in the first compound with the partial structure in the second compound,
wherein
R 1 represents a hydrogen atom, a methyl group, a fluorine atom, or a trifluoromethyl group,
R 2 represents a substituted or unsubstituted aryl group having 6 to 22 carbon atoms,
Y represents a carbon atom,
Y 1 represents a halogen atom, and
X represents —X 1 Z 1 X 2 — which is an atomic group which forms a cyclic structure including a heteroatom together with Y, wherein
Z 1 represents —O—, —S—, —CO—, —COO—, —SO—, or —SO 2 —, and
each of X 1 and X 2 individually represents a single bond, a methylene group, or an alkylene group having 2 to 25 carbon atoms, each of X and X 2 being unsubstituted or substituted with a substituent, and optionally a carbon atom included in X 1 and a carbon atom included in X 2 being bonded via a divalent group.