Copolymer and optical film using same

Patent metadata

Field	Value
Publication number	US-11225540-B2
Application number	US-201716467414-A
Country	US
Kind code	B2
Filing date	Dec 4, 2017
Priority date	Dec 7, 2016
Publication date	Jan 18, 2022
Grant date	Jan 18, 2022

Abstract

A novel copolymer suitable for an optical film which is excellent in optical characteristics and has high retardation even in a thin film state, and an optical film containing the same are provided. A copolymer excellent in optical characteristics and easy to form a composite with a different polymer, and an optical film composed of the same are also provided.

First claim

The invention claimed is:

1. A copolymer, comprising:
a residue unit A of formula (1); and
a residue unit B of formula (2):

wherein R 1 and R 2 each independently represent hydrogen provided that the case where R 1 and R 2 are both hydrogen is excluded, a cyano group, an ester group (—C(═O)OX 1 ), an amide group (—C(═O)N(X 2 )(X 3 )), or an acyl group (—C(═O)X 4 ), where X 1 to X 3 each independently represent a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, and X 4 represents a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic group having 3 to 14 carbon atoms;
R 3 to R 7 each independently represent hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, a cyclic group having 3 to 14 carbon atoms, a halogen, a hydroxy group, a carboxy group, a nitro group, a cyano group, an alkoxy group (—OX 5 ), an ester group (—C(═O)OX 6 ), an amide group (—C(═O)N(X 7 )(X 8 )), an acyl group (—C(═O)X 9 ), an amino group (—N(X 10 )(X 11 )), or a sulfonyl group (—SOOX 12 ), where X 5 to X 8 each independently represent a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, and X 9 to X 12 each independently represent hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms;
at least one of R 3 to R 7 is a hydroxy group; and
adjacent substituents among R 3 to R 7 may form a fused ring structure each other,

wherein R 8 represents an m-membered heterocyclic residue including one or more heteroatoms or a 5-membered or 6-membered ring residue containing no heteroatom, and m represents an integer of 5 to 10; and
the m-membered heterocyclic residue, the 5-membered ring residue, and the 6-membered ring residue may form a fused ring structure with another cyclic structure.

2. The copolymer according to claim 1 , wherein R 1 is selected from the group consisting of a cyano group, an ester group, an amide group, and an acyl group.

3. The copolymer according to claim 1 , wherein R 2 is a cyano group.

4. The copolymer according to claim 1 , wherein R 8 is a 5-membered heterocyclic residue or a 6-membered heterocyclic residue including at least one nitrogen atom or oxygen atom as a heteroatom, and
the 5-membered heterocyclic residue and the 6-membered heterocyclic residue may form a fused ring structure with another cyclic structure.

5. The copolymer according to claim 1 , wherein the residue unit A of the formula (1) is at least one selected from the group consisting of an α-cyanocinnamate ester residue unit, a benzalmalononitrile residue unit, a nitrobenzalmalononitrile residue unit, a cinnamonitrile residue unit, a chalcone residue unit, an alkoxychalcone residue unit, a benzylidenemalonate diester residue unit, and an N,N-dialkylcinnamamide residue unit.

6. The copolymer according to claim 1 ,
wherein the residue unit B is a residue unit of formula (3) and/or a residue unit of formula (4):

wherein R 9 to R 16 each independently represent hydrogen, a halogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, a cyclic group having 3 to 14 carbon atoms, a cyano group, a nitro group, a hydroxy group, a carboxy group, a thiol group, an alkoxy group (—OX 13 ), an ester group (—C(═O)OX 14 or —CO(═O)—X 15 ), an amide group (—C(═O)N(X 16 )(X 17 ) or —NX 18 C(═O)X 19 ), an acyl group (—C(═O)X 20 ), or an amino group (—N(X 21 )(X 22 )), where X 13 to X 15 each independently represent a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic group having 3 to 14 carbon atoms, X 16 to X 22 each independently represent hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic group having 3 to 14 carbon atoms;
adjacent substituents among R 9 to R 16 may form a fused ring structure each other; and
R 9 and R 15 , and, R 10 and R 16 may consist of the same atoms and may form a ring structure,

wherein R 17 to R 20 each independently represent hydrogen, a halogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, a cyclic group having 3 to 14 carbon atoms, a cyano group, a nitro group, a hydroxy group, a carboxy group, a thiol group, an alkoxy group (—OX 23 ), an ester group (—C(═O)OX 24 or —CO(═O)—X 25 ), an amide group (—C(═O)N(X 26 )(X 27 ) or —NX 28 C(═O)X 29 ), an acyl group (—C(═O)X 30 ), or an amino group (—N(X 31 )(X 32 )), where X 23 to X 25 each independently represent a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic group having 3 to 14 carbon atoms, X 26 to X 32 each independently represent hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic group having 3 to 14 carbon atoms;
adjacent substituents among R 17 to R 20 may form a fused ring structure each other; and
R 17 and R 18 , and, R 19 and R 20 may consist of the same atoms and may form a ring structure.

7. The copolymer according to claim 1 , wherein a molar ratio AB of the residue unit A of the formula (1) to the residue unit B of the formula (2) falls within the range of 0.05 to 6.

8. The copolymer according to claim 6 , wherein the copolymer has a number-average molecular weight of 3,000 to 500,000 in terms of standard polystyrene when the residue unit B is a residue unit B of other than the formula (4) or in terms of standard pullulan when the residue unit B is a residue unit of the formula (4).

9. A process for producing the copolymer of claim 1 , comprising:
conducting polymerization of a monomer of formula (5):

wherein R 1 and R 2 each independently represent hydrogen, provided that the case where R 1 and R 2 are both hydrogen is excluded, a cyano group, an ester group (—C(═O)OX 1 ), an amide group (—C(═O)N(X 2 )(X 3 )), or an acyl group (—C(═O)X 4 ), where X 1 to X 3 each independently represent a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, and X 4 represents a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic group having 3 to 14 carbon atoms;
R 3 to R 7 each independently represent hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, a cyclic group having 3 to 14 carbon atoms, a halogen, a hydroxy group, a carboxy group, a nitro group, a cyano group, an alkoxy group (—OX 5 ), an ester group (—C(═O)OX 6 ), an amide group (—C(═O)N(X 7 )(X 8 )), an acyl group (—C(═O)X 9 ), an amino group (—N(X 10 )(X 11 )), or a sulfonic acid group (—

Assignees

• Tosoh Corp

Inventors

• Fujii Yasuyoshi
• Ito Saki

Classifications

• C09D125/18

  Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen · CPC title

• C08F212/32

  containing two or more rings · CPC title

• C08F212/08

  Styrene · CPC title

• G02F1/133634

  the refractive index Nz perpendicular to the element surface being different from in-plane refractive indices Nx and Ny, e.g. biaxial or with normal optical axis · CPC title

• C09D133/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title