# US 8,771,810 B2 · Polymerizable composition, polymer, and film

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- Number: US 8,771,810 B2
- Document ID: US8771810B2
- Status: Granted
- Kind: B2
- Application number: 13/716,386
- Filed: 2012-12-17
- Published: 2013-05-02
- Granted: 2014-07-08
- Earliest claimed: 2010-06-22
- Assignees: FUJIFILM Corporation
- Applicants: FUJIFILM Corporation
- Inventors: Masatoshi Mizumura; Shunya Katoh; Yasuhiro Ishiwata; Masaomi Kimura
- Web page: https://patentgrep.com/patent/US8771810B2

## CPC

- C07C 251/24: having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
- C07C 327/30: having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C08J 5/18: Manufacture of films or sheets
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- C08J 2333/14: of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C09K 2323/03: Viewing layer characterised by chemical composition
- C09K 2323/035: Ester polymer, e.g. polycarbonate, polyacrylate or polyester
- G02B 5/20: Filters (polarising elements G02B5/30)
- G02B 5/3041: {comprising multiple thin layers, e.g. multilayer stacks}
- G02B 5/3083: {Birefringent or phase retarding elements (G02B5/3008, G02B5/3016 take precedence; systems for polarisation control G02B27/286; manufacturing phase modulating patterns by lithographic processes G03F7/001)}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A polymerizable composition containing a compound represented by the formula (I) or the formula (I′) is useful for formation of films having a high Δn with no coloration. P1 and P2 each are a polymerizable group; m1 and m2 each are an integer of from 1 to 10; A1 to A4 each are a predetermined cyclic group; R is a hydrogen atom or an alkyl; in the formula (I), Z1 is —COO—, —COO—, —OCO—CH═CH—, —NHCO— or —NR1CO—; L1 and L2 each are —O—, —S—, —COO—, —COO—, —OCO—CH═CH—, —OCOO—, —NHCO— or —NR1CO; n1 is 1 or 2; in the formula (I′), Z1 and Z2 each are —COO—, —OCO—, —NHCO— or NR1CO; L1 and L2 each are —O—, —S—, —COO—, —OCO—, —OCOO—, —NHCO— or NR1CO; n1 and n2 each are 1 or 2.

## Claims

### Claim 1

A polymerizable composition containing at least one compound represented by the following formula (A):
wherein P1 and P2 each represents a polymerizable group selected from the groups represented by the following formulae (P-1) to (P-5):
wherein R11 to R13 each represents a hydrogen atom or a methyl group;
m1 and m2 each indicates an integer of from 2 to 8, and of m1 or m2 CH2's, one CH2 or two or more CH2's not adjacent to each other may be replaced by an oxygen atom or a sulfur atom;
n1 is 0, 1 or 2;
n2 is 1 or 2;
A1, A2, A3 and A4 each represents a substituted or unsubstituted, 5- to 18-membered aromatic hydrocarbon ring or 5- to 18-membered aromatic hetero ring residue;
R represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms, however, when n1 is 1 or 2, R may be an alkyl group having from 5 to 8 carbon atoms;
Z1 and Z2 each represents —COO—, —OCO—, —NHCO— or —NR1CO—, and R1 represents an alkyl group having from 1 to 10 carbon atoms, however, when n1 is 0, Z2 may be —OCO—CH═CH—;
L1 and L2 each represents —O—, —S—, —COO—, —OCO—, —OCOO—, —NHCO— or —NR1CO, and R1 represents an alkyl group having from 1 to 10 carbon atoms, however, when n1 is 0, L1 and L2 each may be —OCO—CH═CH—.

### Claim 2 (depends on 1)

The polymerizable composition according to claim 1, which contains, as the compound represented by the formula (A), at least one compound represented by the following formula (I):
wherein P1 and P2 each represents a polymerizable group selected from the groups represented by the formulae (P-1) to (P-5) in claim 1;
m1 and m2 each indicates an integer of from 2 to 8, and of m1 or m2 CH2's, one CH2 or two or more CH2's not adjacent to each other may be replaced by an oxygen atom or a sulfur atom;
A1, A2 and A3 each represents a substituted or unsubstituted, 5- to 18-membered aromatic hydrocarbon ring or 5- to 18-membered aromatic hetero ring residue;
R represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
Z1 represents —COO—, —OCO—, —OCO—CH═CH—, —NHCO— or —NR1CO, and R1 represents an alkyl group having from 1 to 10 carbon atoms;
L1 and L2 each represents —O—, —S—, —COO—, —OCO—, —OCO—CH═CH—, —OCOO—, —NHCO— or —NR1CO, and R1 represents an alkyl group having from 1 to 10 carbon atoms; and
n1 is 1 or 2.

### Claim 3 (depends on 2)

The polymerizable composition according to claim 2, wherein A1, A2 and A3 each is an unsubstituted, 5- to 18-membered aromatic hydrocarbon ring or 5- to 18-membered aromatic hetero ring residue, or at least one of A1, A2 and A3 is a 5- to 18-membered aromatic hydrocarbon ring or 5- to 18-membered aromatic hetero ring residue substituted with an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an amide group having from 2 to 5 carbon atoms, an alkoxycarbonyl group having from 2 to 5 carbon atoms, an acyloxy group having from 2 to 5 carbon atoms, an acyl group having from 2 to 5 carbon atoms, a cyano group or a halogen atom.

### Claim 4 (depends on 2)

The polymerizable composition according to claim 2, wherein, in the formula (I), n1 is 1, and A1, A2 and A3 each is 1,4-phenylene optionally having a substituent.

### Claim 5 (depends on 2)

The polymerizable composition according to claim 2, wherein, in the formula (I), L1 and L2 each is —O—, and Z1 is —OCO— or —OCO—CH═CH—.

### Claim 6 (depends on 1)

The polymerizable composition according to claim 1, which contains, as the compound represented by the formula (A), at least one compound represented by the following formula (I′):
wherein P1 and P2 each represents a polymerizable group selected from the groups represented by the formulae (P-1) to (P-5) in claim 1;
m1 and m2 each indicates an integer of from 2 to 8, and of m1 or m2 CH2's, one CH2 or two or more CH2's not adjacent to each other may be replaced by an oxygen atom or a sulfur atom;
A1, A2, A3 and A4 each represents a substituted or unsubstituted, 5- to 18-membered aromatic hydrocarbon ring or 5- to 18-membered aromatic hetero ring residue;
R represents a hydrogen atom or an alkyl group having from 1 to 8 carbon atoms;
Z1 and Z2 each represents —COO—, —OCO—, —NHCO— or —NR1CO—, and R1 represents an alkyl group having from 1 to 10 carbon atoms;
L1 and L2 each represents —O—, —S—, —COO—, —OCO—, —OCOO—, —NHCO— or —NR1CO, and R1 represents an alkyl group having from 1 to 10 carbon atoms; and
n1 and n2 each is 1 or 2.

### Claim 7 (depends on 6)

The polymerizable composition according to claim 6, wherein, in the formula (I′), A2 and A3 each is 1,4-phenylene optionally having a substituent, and n1=n2=1.

### Claim 8 (depends on 7)

The polymerizable composition according to claim 7, wherein, in the formula (I′), A1 and A4 each is 1,4-phenylene.

### Claim 9 (depends on 6)

The polymerizable composition according to claim 6, wherein A1, A2, A3 and A4 each represents an unsubstituted, 5- to 18-membered aromatic hydrocarbon ring or 5- to 18-membered aromatic hetero ring residue, or at least one of A1, A2, A3 and A4 is a 5- to 18-membered aromatic hydrocarbon ring or 5- to 18-membered aromatic hetero ring residue substituted with an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an amide group having from 2 to 5 carbon atoms, an alkoxycarbonyl group having from 2 to 5 carbon atoms, an acyloxy group having from 2 to 5 carbon atoms, an acyl group having from 2 to 5 carbon atoms, a cyano group or a halogen atom.

### Claim 10 (depends on 1)

The polymerizable composition according to claim 1, wherein, in the formula (A), P1 and P2 each is a methacrylate group or an acrylate group.

### Claim 11 (depends on 1)

The polymerizable composition according to claim 1, which further contains at least one chiral compound.

### Claim 12

A polymer produced by polymerizing a polymerizable composition containing at least one compound represented by the following formula (A):
wherein P1 and P2 each represents a polymerizable group selected from the groups represented by the following formulae (P-1) to (P-5):
wherein R11 to R13 each represents a hydrogen atom or a methyl group;
m1 and m2 each indicates an integer of from 2 to 8, and of m1 or m2 CH2's, one CH2 or two or more CH2's not adjacent to each other may be replaced by an oxygen atom or a sulfur atom;
n1 is 0, 1 or 2;
n2 is 1 or 2;
A1, A2, A3 and A4 each represents a substituted or unsubstituted, 5- to 18-membered aromatic hydrocarbon ring or 5- to 18-membered aromatic hetero ring residue;
R represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms, however, when n1 is 1 or 2, R may be an alkyl group having from 5 to 8 carbon atoms;
Z1 and Z2 each represents —COO—, —OCO—, —NHCO— or —NR1CO—, and R1 represents an alkyl group having from 1 to 10 carbon atoms, however, when n1 is 0, Z2 may be —OCO—CH═CH—;
L1 and L2 each represents —O—, —S—, —COO—, —OCO—, —OCOO—, —NHCO— or —NR1CO, and R1 represents an alkyl group having from 1 to 10 carbon atoms, however, when n1 is 0, L1 and L2 each may be —OCO—CH═CH—.

### Claim 13

A film containing at least one polymer produced by polymerizing a polymerizable composition containing at least one compound represented by the following formula (A):
wherein P1 and P2 each represents a polymerizable group selected from the groups represented by the following formulae (P-1) to (P-5):
wherein R11 to R13 each represents a hydrogen atom or a methyl group;
m1 and m2 each indicates an integer of from 2 to 8, and of m1 or m2 CH2's, one CH2 or two or more CH2's not adjacent to each other may be replaced by an oxygen atom or a sulfur atom;
n1 is 0, 1 or 2;
n2 is 1 or 2;
A1, A2, A3 and A4 each represents a substituted or unsubstituted, 5- to 18-membered aromatic hydrocarbon ring or 5- to 18-membered aromatic hetero ring residue;
R represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms, however, when n1 is 1 or 2, R may be an alkyl group having from 5 to 8 carbon atoms;
Z1 and Z2 each represents —COO—, —OCO—, —NHCO— or —NR1CO—, and R1 represents an alkyl group having from 1 to 10 carbon atoms, however, when n1 is 0, Z2 may be —OCO—CH═CH—;
L1 and L2 each represents —O—, —S—, —COO—, —OCO—, —OCOO—, —NHCO— or —NR1CO, and R1 represents an alkyl group having from 1 to 10 carbon atoms, however, when n1 is 0, L1 and L2 each may be —OCO—CH═CH—.

### Claim 14 (depends on 13)

The film according to claim 13, wherein the polymerizable composition further contains at least one chiral compound, and the film is produced by fixing the cholesteric liquid-crystal phase of the polymerizable composition.

### Claim 15 (depends on 13)

The film according to claim 13, which shows optical anisotropy.

### Claim 16 (depends on 13)

The film according to claim 13, which shows selective reflection characteristics.

### Claim 17 (depends on 16)

The film according to claim 16, which shows selective reflection characteristics in the IR wavelength range.

### Claim 18 (depends on 13)

The film according to claim 13, which is colorless.