(Meth)acrylate, polymer and resist composition
View Patent ↗A polymer contains a constituent unit having a specific acetal skeleton. This polymer is able to be used as a resist resin in DUV excimer laser lithography, electron beam lithography, EUV lithography, or the like.
1. A copolymer consisting essentially of:
a constituent unit consisting of a monomer represented by the following formula (1):
wherein
R represents a hydrogen atom or a methyl group,
R 1 represents a methyl group and
R 2 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, or
R 1 and R 2 are combined with each other to form a ring structure;
A 1 represents a single bond, alkylene, oxyalkylene, —C(O)O—, or —CH 2 CH 2 OC(O)—;
A 2 represents a single bond, alkylene, oxyalkylene, —CO—, —C(O)O—, or —C(O)OCH 2 CH 2 —; and
Z represents a cyclohexane ring, norbornane ring, bicyclo[2.2.2]octane ring, or tetracyclo[4.4.0.1 2,5 .1 7,10 ]dodecane ring, all of which may have a substituent;
one or more constituent units derived from a monomer having a lactone structure in a molecule, and,
one or more constituent units derived from a monomer containing an alicylic skeleton having a hydroxy group or a cyano group in a molecule, and
one or more constituent units derived from monomers selected from the group consisting of monomers represented by the following formulae (6-1), (6-2), (6-4), (6-5), (6-14), (6-15), (6-16), (6-18), (6-57), (6-58), (6-65), (6-66), and (6-67):
wherein R represents a hydrogen atom or a methyl group.
2. A copolymer according to claim 1 , further comprising one or more constituent units derived from monomers selected from the group consisting of monomers represented by the following formulae (6-22) and (6-64):
wherein R represents a hydrogen atom or a methyl group.
3. A resin composition comprising the copolymer according to claim 1 .
4. A pattern forming method comprising the steps of:
coating the resist composition according to claim 1 on a to-be-processed substrate,
exposing the coated substrate to light having a wavelength of 250 nm or less, and
developing the exposed substrate using a developing solution to form a pattern.
5. A copolymer consisting essentially of:
a constituent unit consisting of a monomer represented by the following formula (1):
wherein
R represents a hydrogen atom or a methyl group,
R 1 represents a methyl group and
R 2 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, or
R 1 and R 2 are combined with each other to form a ring structure;
A 1 represents a single bond, alkylene, oxyalkylene, —C(O)O—, or —CH 2 CH 7 OC(O)—;
A 2 represents a single bond, alkylene, oxyalkylene, —CO—, —C(O)O—, or —C(O)OCH 2 CH 2 —; and
Z represents a cyclohexane ring, norbornane ring, bicyclo[2.2.2]octane ring, or tetracyclo[4.4.0.1 2,5 .1 7,10 ]dodecane ring, each of which may have a substituent;
one or more units derived from a monomer having a lactone structure in a molecule, and,
one or more constituent units derived from a monomer containing an alicylic skeleton having a hydroxy group or a cyano group in a molecule;
wherein said one or more constituent units derived from a monomer containing an alicylic skeleton having a hydroxy group or a cyano group in a molecule are selected from constituent units derived from a monomer selected from the group consisting of: monomers represented by the following formulae (6-19) and (6-74):
wherein R represents a hydrogen atom or a methyl group.
6. A copolymer consisting essentially of: a constituent unit derived from a monomer represented by the following formula (3):
wherein
R represents a hydrogen atom or a methyl group,
R 1 represents a methyl group and
R 2 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,
A 1 represents a single bond, alkylene, oxyalkylene, —C(O)O—, or —CH 2 CH 2 OC(O)—;
A 2 represents a single bond, alkylene, oxyalkylene, —CO—, —C(O)O—, or —C(O)OCH 2 CH 2 —; and
Z represents a cyclohexane ring which may have a substituent; and
one or more constituent units derived from one or more monomers containing a lactone structure in the molecule.
7. A copolymer consisting essentially of: a constituent unit derived from a monomer represented by the following formula (3):
wherein
R represents a hydrogen atom or a methyl group,
R 1 represents a methyl group and
R 2 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,
A 1 represents a single bond, alkylene, oxyalkylene, —C(O)O—, or —CH 2 CH 2 OC(O)—;
A2 represents a single bond, alkylene, oxyalkylene, —CO—, —C(O)O—, or —C(O)OCH 2 CH 2 —; and
Z represents bicyclo[2.2.2]octane ring which may have a substituent; and
one or more constituent units derived from one or more monomers containing a lactone structure in the molecule.
8. A copolymer consisting essentially of:
25 to 70 mol % of a constituent unit represented by the following formula (1):
wherein
R represents a hydrogen atom or a methyl group,
R 1 represents a methyl group and
R 2 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, or
R 1 and R 2 are combined with each other to form a ring structure;
A 1 represents a single bond, alkylene, oxyalkylene, —C(O)O—, or —CH 2 CH 2 OC(O)—;
A 2 represents a single bond, alkylene, oxyalkylene, —CO—, —C(O)O—, or —C(O)OCH 2 CH 2 —; and
Z represents a norbornane ring which may have a substituent;
25 to 70 mol % of a constituent unit derived from at least one monomer containing a lactone structure in the molecule; and
5 to 20 mol % of a constituent unit derived from at least one monomer selected from the group consisting of a monomer containing alicyclic skeleton having a hydroxy group and a monomer containing alicyclic skeleton having a cyano group.
9. A copolymer consisting essentially of:
25 to 70 mol % of a constituent unit represented by the following formula (1):
wherein
R represents a hydrogen atom or a methyl group,
R 1 represents a methyl group and
R 2 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, or
R 1 and R 2 are combined with each other to form a ring structure;
A 1 represents a single bond, alkylene, oxyalkylene, —C(O)O—, or —CH 2 CH 2 OC(O)—;
A 2 represents a single bond, alkylene, oxyalkylene, —CO—, —C(O)O—, or —C(O)OCH 2 CH 2 —; and
Z represents a bicyclo[2.2.2]octane ring which may have a substituent;
25 to 70 mol % of a constituent unit derived from at least one monomer containing a lactone structure in the molecule; and
5 to 20 mol % of a constituent unit derived from at least one monomer selected from the group consisting of a monomer containing alicyclic skeleton having a hydroxy group and a monomer containing alicyclic skeleton having a cyano group.
10. A copolymer consisting essentially of:
25 to 70 mol % of a constituent unit represented by the following formula (1):
wherein
R represents a hydrogen atom or a methyl group,
R 1 represents a methyl group and
R 2 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, or
R 1 and R 2 are combined with each other to form a ring structure;
A 1 represents a single bond, alkylene, oxyalkylene, —C(O)O—, or —CH 2 CH 2 OC(O)—;
A 2 represents a single bond, alkylene, oxyalkylene, —CO—, —C(O)O—, or —C(O)OCH 2 CH 2 —; and
Z represents a tetracyclo[4.4.0.1 2,5 .1 7,10 ]dodecane ring which may have a substituent;
25 to 70 mol % of a constituent unit derived from at least one monomer containing a lactone structure in the molecule; and
5 to 20 mol % of a constituent unit derived from at least one monomer selected from the group consisting of a monomer containing alicyclic skeleton having a hydroxy group and a monomer containing alicyclic skeleton having a cyano group.
11. A copolymer consisting essentially of:
a constituent unit consisting of a monomer represented by the following formula (1):
wherein
R represents a hydrogen atom or a methyl group,
R 1 represents a methyl group and
R 2 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, or
R 1 and R 2 are combined with each other to form a ring structure;
A 1 represents a single bond, alkylene, oxyalkylene, —C(O)O—, or —CH 2 CH 2 OC(O)—;
A 2 represents a single bond, alkylene, oxyalkylene, —CO—, —C(O)O—, or —C(O)OCH 2 CH 2 —; and
Z represents a cyclohexane ring, norbornane ring, bicyclo[2.2.2]octane ring, or tetracyclo[4.4.0.1 2,5 .1 7,10 ]dodecane ring, each of which may have a substituent;
one or more units derived from a monomer having a lactone structure in a molecule,
one or more constituent units derived from monomers selected from the group consisting of: monomers represented by the following formulae (6-1), (6-2), (6-4), (6-5), (6-14), (6-15), (6-16), (6-18), (6-57), (6-58), (6-65), (6-66), and (6-67):
wherein R represents a hydrogen atom or a methyl group, and
one or more constituent units derived from monomers selected from the group consisting of monomers represented by the following formulae (6-22) and (6-64):
wherein R represents a hydrogen atom or a methyl group.
12. A copolymer consisting essentially of:
a constituent unit consisting of a monomer represented by the following formula (1):
wherein
R represents a hydrogen atom or a methyl group,
R 1 represents a methyl group and
R 2 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, or
R 1 and R 2 are combined with each other to form a ring structure;
A 1 represents a single bond, alkylene, oxyalkylene, —C(O)O—, or —CH 2 CH 2 OC(O)—;
A 2 represents a single bond, alkylene, oxyalkylene, —CO—, —C(O)O—, or —C(O)OCH 2 CH 2 —; and
Z represents a cyclohexane ring, norbornane ring, bicyclo[2.2.2]octane ring, or tetracyclo[4.4.0.1 2,5 .1 7,10 ]dodecane ring, all of which may have a substituent;
one or more units derived from a monomer having a lactone structure in a molecule,
one or more constituent units derived from a monomer containing an alicylic skeleton having a hydroxy group or a cyano group in a molecule, and
one or more constituent units derived from monomers selected from the group consisting of monomers represented by the following formulae (6-22) and (6-64):
wherein R represents a hydrogen atom or a methyl group.