Cholesteric liquid crystal mixture, film, IR reflection plate, laminate, and laminated glass

Patent metadata

Field	Value
Publication number	US-9534727-B2
Application number	US-201414497767-A
Country	US
Kind code	B2
Filing date	Sep 26, 2014
Priority date	Mar 28, 2012
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

A cholesteric liquid crystal mixture containing a compound represented by Z 1 —Y 1 -A 1 -Y 3 -M 1 -Y 4 -A 2 -Y 2 —Z 2 , a compound represented by Z 3 —Y 5 -A 3 -Y 7 -M 2 -P, and a tri- or higher functional polymerizable monomer suppresses deposition of a liquid crystal at the time of forming a film, exhibits a wide characteristic reflection bandwidth of the film. Z 1 to Z 3 represent a polymerizable group; A 1 to A 3 represent an alkylene spacer having a chain of 1 to 30 atoms; M 1 and M 2 represent (-T 1 -Y 8 ) n -T 2 -; n indicates a natural number; T 1 and T 2 represent a hydrocarbon or heterocyclic ring; Y 1 to Y 5 , Y 7 and Y 8 represent a single bond, —O—, —CO—, —O—CO—, —CO—O— or —O—CO—O—; and P represents a hydrogen atom or an alkyl group.

First claim

What is claimed is:

1. A cholesteric liquid crystal mixture, containing a compound represented by the following general formula (Ia), a compound represented by the following general formula (Ib), and a tri- or higher functional polymerizable monomer:
Z 1 —Y 1 -A 1 -Y 3 -M 1 -Y 4 -A 2 -Y 2 —Z 2 ,  General Formula (Ia)

Z 3 —Y 5 -A 3 -Y 7 -M 2 -P  General Formula (Ib)

wherein Z 1 , Z 2 and Z 3 each independently represent an acryloyl group or a methacryloyl group; A 1 , A 2 and A 3 each independently represent an alkylene group having an atom-bonding chain length of 1 to 12; M 1 and M 2 each independently represent (-T 1 -Y 8 ) n -T 2 -; n indicates 2, multiple (-T 1 -Y 8 )'s may be the same or different; T 1 and T 2 each independently represent a 1,4-phenylene group, provided that the 1,4-phenylene group may have a substituent; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 7 and Y 8 each independently represent —O—, —CO—, —O—CO—, —CO—O— or —O—CO—O—; and P represents an alkyl group having 1 to 15 carbon atoms.

2. The cholesteric liquid crystal mixture according to claim 1 , wherein the tri- or higher polymerizable monomer is contained in an amount of 0.1% by mass to 10% by mass with respect to the total amount of the liquid crystal compound contained in the cholesteric liquid crystal mixture.

3. The cholesteric liquid crystal mixture according to claim 1 , further containing a polymerization initiator.

4. The cholesteric liquid crystal mixture according to claim 1 , wherein T 1 and T 2 in the general formulae (Ia) and (Ib) each independently represent a 1-4-phenylene group, provided that the 1,4-phenylene group may have an alkyl group or an alkoxy group as a substituent.

5. The cholesteric liquid crystal mixture according to claim 1 , wherein:
the compound represented by the general formula (Ia) is a compound in which at least one 1,4-phenylene group of the 1,4-phenylene group represented by T 1 and T 2 has an alkyl group or an alkoxy group, and
the compound represented by the general formula (Ib) is a compound in which T 1 and T 2 each are an unsubstituted 1,4-phenylene group.

6. A film comprising a liquid crystal film obtained by fixing a cholesteric liquid crystal phase formed by polymerizing a cholesteric liquid crystal mixture, wherein:
the cholesteric liquid crystal mixture contains a compound represented by the following general formula (Ia), a compound represented by the following general formula (Ib), and a tri- or higher functional polymerizable monomer:
Z 1 —Y 1 -A 1 -Y 3 -M 1 -Y 4 -A 2 -Y 2 —Z 2 ,  General Formula (Ia)

Z 3 —Y 5 -A 3 -Y 7 -M 2 -P  General Formula (Ib)

wherein Z 1 , Z 2 and Z 3 each independently represent an acryloyl group or a methacryloyl group; A 1 , A 2 and A 3 each independently represent an alkylene group having an atom-bonding chain length of 1 to 12; M 1 and M 2 each independently represent (-T 1 -Y 8 ) n -T 2 -; n indicates 2, multiple (-T 1 -Y 8 )'s may be the same or different; T 1 and T 2 each independently represent a 1,4-phenylene group, provided that the 1,4-phenylene group may have a substituent; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 7 and Y 8 each independently represent —O—, —CO—, —O—CO—, —CO—O— or —O—CO—O—; and P represents an alkyl group having 1 to 15 carbon atoms.

7. The film according to claim 6 , further comprising two or more liquid crystal films obtained by fixing the cholesteric liquid crystal phase therein.

8. The film according to claim 6 , wherein a selective reflection characteristic is exhibited in an IR wavelength region.

9. An IR reflection plate, comprising a film comprising a liquid crystal film obtained by fixing a cholesteric liquid crystal phase formed by polymerizing a cholesteric liquid crystal mixture, wherein:
the cholesteric liquid crystal mixture contains a compound represented by the following general formula (Ia), a compound represented by the following general formula (Ib), and a tri- or higher functional polymerizable monomer:
Z 1 —Y 1 -A 1 -Y 3 -M 1 -Y 4 -A 2 -Y 2 —Z 2 ,  General Formula (Ia)

Z 3 —Y 5 -A 3 -Y 7 -M 2 -P  General Formula (Ib)

wherein Z 1 , Z 2 and Z 3 each independently represent an acryloyl group or a methacryloyl group; A 1 , A 2 and A 3 each independently represent an alkylene group having an atom-bonding chain length of 1 to 12; M 1 and M 2 each independently represent (-T 1 -Y 8 ) n -T 2 -; n indicates 2, multiple (-T 1 -Y 8 )'s may be the same or different; T 1 and T 2 each independently represent a 1,4-phenylene group, provided that the 1,4-phenylene group may have a substituent; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 7 and Y 8 each independently represent —O—, —CO—, —O—CO—, —CO—O— or —O—CO—O—; and P represents an alkyl group having 1 to 15 carbon atoms.

10. The IR reflection plate according to claim 9 , comprising a λ/2 plate.

11. A laminate which is formed by the use of an IR reflection plate and includes an interlayer film on any one of an outmost layer of a liquid crystal film obtained by fixing the cholesteric liquid crystal phase of the IR reflection plate, wherein:
the IR reflection plate comprises a film which comprises a liquid crystal film obtained by fixing a cholesteric liquid crystal phase formed by polymerizing a cholesteric liquid crystal mixture, and
the cholesteric liquid crystal mixture contains a compound represented by the following general formula (Ia), a compound represented by the following general formula (Ib), and a tri- or higher functional polymerizable monomer:
Z 1 —Y 1 -A 1 -Y 3 -M 1 -Y 4 -A 2 -Y 2 —Z 2 ,  General Formula (Ia)

Z 3 —Y 5 -A 3 -Y 7 -M 2 -P  General Formula (Ib)

wherein Z 1 , Z 2 and Z 3 each independently represent an acryloyl group or a methacryloyl group; A 1 , A 2 and A 3 each independently represent an alyllene group having an atom-bonding chain length of 1 to 12; M 1 and M 2 each independently represent (-T 1 -Y 8 ) n -T 2 -; n indicates 2, multiple (-T 1 -Y 8 )'s may be the same or different; T 1 and T 2 each independently represent a 1,4-phenylene group, provided that the 1,4-phenylene group may have a substituent; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 7 and Y 8 each independently represent —O—, —CO—, —O—CO—, —CO—O— or —O—CO—O—; and P represents an alkyl group having 1 to 15 carbon atoms.

12. The laminate according to claim 11 , wherein the interlayer film is a resin interlayer film containing polyvinyl butyral as a main component.

13. A laminated glass comprising a laminate and at least two sheets of glass plates, wherein:
the laminate is inserted into the two sheets of glass,
the laminate is formed by the use of an IR reflection plate and includes an interlayer film on any one of an outmost layer of a liquid crystal film obtained by fixing the cholesteric liquid crystal phase of the IR reflection plate,
the IR reflection plate comprises a film which comprises a liquid crystal film obtained by fixing a cholesteric liquid crystal phase formed by polymerizing a cholesteric liquid crystal mixture, and
the cholesteric liquid crystal mixture contains a compound represented by the following general formula (Ia), a compound represented by the following general formula (Ib), and a tri- or higher functional polymerizable monomer:
Z 1 —Y 1 -A 1 -Y 3 -M 1 -Y 4 -A 2 -Y 2 —Z 2 ,  General Formula (Ia)

Z 3 —Y 5 -A 3 -Y 7 -M 2 -P  General Formula (Ib)

wherein Z 1 , Z 2 and Z 3 each independently represent an acryloyl group or a methacryloyl group; A 1 , A 2 and A 3 each independently represent an alkylene group having an atom-bonding chain length of 1 to 12; M 1 and M 2 each independently represent (-T 1 -Y 8 ) n -T 2 -; n in

Assignees

• Fujifilm Corp

Inventors

• Tasaka Tomoki
• Kimura Masaomi
• Nakajima Masao
• Hashizume Taro

Classifications

• C09K19/3475 Primary

  the heterocyclic ring being a six-membered aromatic ring containing at least three nitrogen atoms · CPC title

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• Y10T428/31859

  Next to an aldehyde or ketone condensation product · CPC title

• C09K2019/0429

  the specific unit being a carbocyclic or heterocyclic discotic unit · CPC title

• C09K2219/03

  in the form of films, e.g. films after polymerisation of LC precursor · CPC title