Copolymer for organic antireflective film, monomer, and composition comprising the copolymer

1. A copolymer for organic antireflective films, comprising a repeating unit represented by the following formula (1):

wherein in the formula (1), R 1 represents any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, and a heteroalkyl group having 1 to 6 carbon atoms;

R 2 represents any one selected from the group consisting of CR′R″, NR′, O and S; R′ and R″ each independently represent any one selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 5 carbon atoms;

R 3 is any one selected from the group consisting of groups represented by the following formulas (1-1) to (1-8):

m and n satisfy the following relations: m+n=1, 0.05<m/(m+n)<0.95, and 0.05<n/(m+n)<0.95; and

A represents the following formula (2) or formula (3):

wherein in the formula (2), R 4 represents any one selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 10 carbon atoms;

R 5 represents any one selected from the group consisting of a hydrogen atom, an alkyl group, a heteroalkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an arylalkyl group and a heteroarylalkyl group, and at least one hydrogen atom contained in R 5 is substituted by any one selected from the group consisting of a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group and combinations thereof; and

wherein in the formula (3), R 6 represents any one selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, a heteroalkyl group and a cycloheteroalkyl group

wherein in the formulas (1-1) to (1-8),

X 11 , X 21 , X 22 , X 31 , X 32 , X 33 , X 51 , X 52 , X 61 , X 62 , X 71 , X 72 , X 73 , X 81 and X 82 each independently represent any one selected from the group consisting of a halogen atom, a cyano group, a nitro group, a phenyl group and perfluoroalkyl group;

R′″ represents any one selected from the group consisting of a hydrogen atom and a methyl group; X 41 represents a halogen atom; a represents an integer from 1 to 3; b represents an integer from 1 to 3, the sum a+b is 3;

X 63 represents any one selected from the group consisting of O, NR′, S and CO;

p11 represents an integer from 1 to 5;

p21 and p22 each independently represent an integer from 1 to 4, the sum of p21 and p22 does not exceed 5;

p31 to p33 each independently represent an integer from 1 to 3, the sum of p31 to p33 does not exceed 5;

p41 represents an integer from 1 to 5;

p51 and p52 each independently represent an integer from 1 to 5, the sum of p51 and p52 does not exceed 9;

p61 and p62 each independently represent an integer from 1 to 5, the sum of p61 and p62 does not exceed 9;

p71 and p73 each independently represent an integer from 1 to 5, p72 represents an integer from 1 to 2, the sum of p71 to p73 does not exceed 9;

p81 represents an integer from 1 to 4; p82 represents an integer from 1 to 3; and the sum of p81 and p82 does not exceed 6, and wherein the copolymer has a weight-average molecular weight as calculated relative to polystyrene standards of 5,000 g/mol to 20,000 g/mol.

2. A copolymer for organic antireflective films comprising any one selected from the group consisting of repeating units represented by the following formulas (2-1) to (2-6):

wherein in the formulas (2-1) to (2-6), X′ 11 , X′ 21 , X′ 31 , X′ 32 , X′ 41 , X′ 42 , X′ 51 , X′ 52 , X′ 61 and X′ 62 each independently represent any one selected from the group consisting of a halogen atom, a perfluoroalkyl group, a cyano group, a nitro group and a phenyl group;

m and n satisfy the following relations: m+n=1, 0.05<m/(m+n)<0.95, and 0.05<n/(m+n)<0.95;

p′11 and p′12 each independently represent an integer from 1 to 5;

p′31, p′32, p′41 and p′42 each independently represent an integer from 1 to 4, the sum of p′31 and p′32 does not exceed 5; the sum of p′41 and p′42 does not exceed 5;

p′51 and p′61 each independently represent an integer from 1 to 5; and p′52 and p′62 each independently represent an integer from 1 to 4.

3. A composition for organic antireflective films, comprising a copolymer having a repeating unit represented by the following formula (1):

wherein in the formula (1), R 1 represents any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, and a heteroalkyl group having 1 to 6 carbon atoms; R 2 represents any one selected from the group consisting of CR′R″, NR′, O and S; R′ and R″ each independently represent any one selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 5 carbon atoms; R 3 is any one selected from the group consisting of groups represented by the following formulas (1-1) to (1-8); m and n satisfy the following relations: m+n=1, 0.05<m/(m+n)<0.95, and 0.05<n/(m+n)<0.95; and A represents the following formula (2) or formula (3):

wherein in the formula (2), R 4 represents any one selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 10 carbon atoms; R 5 represents any one selected from the group consisting of a hydrogen atom, an alkyl group, a heteroalkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an arylalkyl group and a heteroarylalkyl group, and at least one hydrogen atom contained in R 5 is substituted by any one selected from the group consisting of a hydroxyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group and combinations thereof;

wherein in the formula (3), R 6 represents any one selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, a heteroalkyl group and a cycloheteroalkyl group;

wherein in the formulas (1-1) to (1-8),

X 11 , X 21 , X 22 , X 31 , X 32 , X 33 , X 51 , X 52 , X 61 , X 62 , X 71 , X 72 , X 73 , X 81 and X 82 each independently represent any one selected from the group consisting of a halogen atom, a cyano group, a nitro group and a phenyl group;

R′″ represents any one selected from the group consisting of a hydrogen atom and a methyl group; X 41 represents a halogen atom; a represents an integer from 1 to 3; b represents an integer from 1 to 3, the sum a+b is 3;

X 63 represents any one selected from the group consisting of O, NR′, S and CO;

p11 represents an integer from 1 to 5;

p21 and p22 each independently represent an integer from 1 to 4, the sum of p21 and p22 does not exceed 5;

p31 to p33 each independently represent an integer from 1 to 3, the sum of p31 to p33 does not exceed 5;

p41 represents an integer from 1 to 5;

p51 and p52 each independently represent an integer from 1 to 5, the sum of p51 and p52 does not exceed 9;

p61 and p62 each independently represent an integer from 1 to 5, the sum of p61 and p62 does not exceed 9;

p71 and p73 each independently represent an integer from 1 to 5, p72 represents an integer from 1 to 2, the sum of p71 to p73 does not exceed 9;

p81 represents an integer from 1 to 4; p82 represents an integer from 1 to 3; and the sum of p81 and p82 does not exceed 6.

4. A composition for organic antireflective films, comprising the copolymer according to claim 2 .

5. The copolymer for organic antireflective films according to claim 2 , wherein the copolymer for organic antireflective films has a weight average molecular weight as calculated relative to polystyrene standards of 1,000 g/mol to 100,000 g/mol.

6. The composition for organic antireflective films according to claim 3 , wherein the copolymer for organic antireflective films has a weight average molecular weight as calculated relative to polystyrene standards of 1,000 g/mol to 100,000 g/mol.