CHOLESTERIC LIQUID CRYSTAL MIXTURE, FILM, SELECTIVE REFLECTIVE PLATE, LAMINATE, LAMINATED GLASS

• US 20140192286A1
• Filed: 03/11/2014
• Published: 07/10/2014
• Est. Priority Date: 09/12/2011
• Status: Active Grant

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Inventors: TASAKA, Tomoki, ISHIWATA, Yasuhiro, UEMURA, Minoru, TAGUCHI, Takao, KATOH, Shunya, NAKAJIMA, Masao
• Granted Patent: US 9,481,830 B2
• Time in Patent Office: Days
• US Class Current: 349/16
• CPC Class Codes: B32B 17/10005 laminated safety glass or glazing
• CPC Class Codes: B32B 17/10036 comprising two outer glass sheets
• CPC Class Codes: B32B 17/10293 Edge features, e.g. inserts or holes
• CPC Class Codes: B32B 17/10504 Liquid crystal layer
• CPC Class Codes: B32B 17/10761 containing vinyl acetal
• CPC Class Codes: B32B 2367/00 Polyesters, e.g. PET, i.e. polyethylene terephthalate
• CPC Class Codes: B60J 3/04 adjustable in transparency
• CPC Class Codes: C09K 19/2007 the chain containing -COO- or -OCO- groups
• CPC Class Codes: C09K 19/56 Aligning agents
• CPC Class Codes: C09K 2019/0448 the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
• CPC Class Codes: C09K 2019/2078 Ph-COO-Ph-COO-Ph
• CPC Class Codes: G02B 5/208 for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
• CPC Class Codes: G02B 5/3016 involving passive liquid crystal elements optical properties of liquid crystals G02F1/0063; polarising elements associated with active liquid crystal devices G02F1/133528
• CPC Class Codes: G02F 2201/343 cholesteric liquid crystal reflector

Abstract

A cholesteric liquid-crystal mixture containing a compound represented by the general formula (Ia), a compound represented by the general formula (Ib), a fluorine-containing horizontal alignment agent and a polymerization initiator is capable of forming a film which is prevented from precipitation of liquid-crystal compounds therein, of which the haze is reduced and which has a broad reflection width.

Z¹—Y¹-A¹-Y³-M¹-Y⁴-A²-Y²—Z²  General Formula (Ia)

Z³—Y⁵-A³-Y⁷-M²-P  General Formula (Ib)

Claims

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), a fluorine-containing horizontal alignment agent and a polymerization initiator:

Z¹—

Y¹-A¹-Y³-M¹-Y⁴-A²-Y²—

Z² 

 

General Formula (Ia)

Z³—

Y⁵-A³-Y⁷-M²-P 

 

General Formula (Ib)

wherein, in the general formulae (Ia) and (Ib), Z¹, Z² and Z³ each independently represent a polymerizable group;

A¹, A² and A³ each independently represent a spacer having an atom-bonding chain length of from 1 to 30, provided that the spacer represents an alkylene group, or a linking group of multiple alkylene groups bonding to each other via —

O—

or —

CO—

;

M¹ and M² each independently represent (-T¹-Y⁸)_n-T²-;

n indicates a natural number;

when n is 2 or more, then multiple (-T¹-Y⁸)'"'"'s may be the same or different;

T¹ and T² each independently represent a saturated or unsaturated hydrocarbon ring, or a saturated or unsaturated hetero ring, provided that the hydrocarbon ring and the hetero ring may have a substituent;

Y¹, Y², Y³, Y⁴, Y⁵, Y⁷, and Y⁸ each independently represent a single bond, —

O—

, —

CO—

, —

O—

CO—

, —

CO—

O—

or —

O—

CO—

O—

;

P represents a hydrogen atom or an alkyl group having from 1 to 15 carbon atoms.

2. The cholesteric liquid-crystal mixture according to claim 1, wherein T¹ and T² in the general formulae (Ia) and (Ib) each independently represent a saturated or unsaturated hydrocarbon ring, or a saturated or unsaturated hetero ring, provided that the hydrocarbon ring and the hetero ring may have an alkyl group or an alkoxy group as the substituent.

3. The cholesteric liquid-crystal mixture according to claim 1, wherein the content of the compound represented by the general formula (Ib) relative to the content of the compound represented by the general formula (Ia) is from 5 to 40% by mass.

4. 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 hydrocarbon ring or hetero ring of the hydrocarbon ring and the hetero ring represented by T¹ and T² has an alkyl group or an alkoxy group, and the compound represented by the general formula (Ib) is a compound in which the hydrocarbon ring and the hetero ring represented by T¹ and T² each are an unsubstituted hydrocarbon ring or hetero ring.

5. The cholesteric liquid-crystal mixture according to claim 1, wherein in the compound represented by the general formula (Ia), n that indicates M¹ is from 2 to 4.

6. A film comprising a support and, as formed on the support, a liquid-crystal layer in which a cholesteric liquid-crystal phase formed by polymerizing s cholesteric liquid-crystal mixture is fixed, 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), a fluorine-containing horizontal alignment agent and a polymerization initiator:

Z¹—

Y¹-A¹-Y³-M¹-Y⁴-A²-Y²—

Z² 

 

General Formula (Ia)

Z³—

Y⁵-A³-Y⁷-M²-P 

 

General Formula (Ib)

wherein, in the general formulae (Ia) and (Ib), Z¹, Z² and Z³ each independently represent a polymerizable group;

A¹, A² and A³ each independently represent a spacer having an atom-bonding chain length of from 1 to 30, provided that the spacer represents an alkylene group, or a linking group of multiple alkylene groups bonding to each other via —

O—

or —

CO—

;

M¹ and M² each independently represent (-T¹-Y⁸)_n-T²-;

n indicates a natural number;

when n is 2 or more, then multiple (-T¹-Y⁸)'"'"'s may be the same or different;

T¹ and T² each independently represent a saturated or unsaturated hydrocarbon ring, or a saturated or unsaturated hetero ring, provided that the hydrocarbon ring and the hetero ring may have a substituent;

Y¹, Y², Y³, Y⁵, Y⁷ and Y⁸ each independently represent a single bond, —

O—

, —

CO—

, —

O—

CO—

, —

CO—

O—

or —

O—

CO—

O—

;

P represents a hydrogen atom or an alkyl group having from 1 to 15 carbon atoms.

7. The film according to claim 6, containing two or more liquid-crystal layers each with the cholesteric liquid-crystal phase fixed therein.

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

9. The film according to claim 6, exhibiting a selective reflection characteristic in a UV or visible wavelength region.

10. A selective reflector comprising a film comprising a support and, as formed on the support, a liquid-crystal layer in which a cholesteric liquid-crystal phase formed by polymerizing s cholesteric liquid-crystal mixture is fixed, 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), a fluorine-containing horizontal alignment agent and a polymerization initiator:

Z¹—

Y¹-A¹-Y³-M¹-Y⁴-A²-Y²—

Z² 

 

General Formula (Ia)

Z³—

Y⁵-A³-Y⁷-M²-P 

 

General Formula (Ib)

wherein, in the general formulae (Ia) and (Ib), Z¹, Z² and Z³ each independently represent a polymerizable group;

A¹, A² and A³ each independently represent a spacer having an atom-bonding chain length of from 1 to 30, provided that the spacer represents an alkylene group, or a linking group of multiple alkylene groups bonding to each other via —

O—

or —

CO—

;

M¹ and M² each independently represent (-T¹-Y⁸)_n-T²-;

n indicates a natural number;

when n is 2 or more, then multiple (-T¹-Y⁸)'"'"'s may be the same or different;

T¹ and T² each independently represent a saturated or unsaturated hydrocarbon ring, or a saturated or unsaturated hetero ring, provided that the hydrocarbon ring and the hetero ring may have a substituent;

Y¹, Y², Y³, Y⁴, Y⁵, Y⁷ and Y⁸ each independently represent a single bond, —

O—

, —

CO—

, —

O—

CO—

, —

CO—

O—

or —

O—

CO—

O—

;

P represents a hydrogen atom or an alkyl group having from 1 to 15 carbon atoms.

11. The selective reflector according to claim 10, containing a λ

/2 plate.

12. The selective reflector according to claim 10, having a highly-adhesive layer as the outermost layer.

13. A laminate which is formed by the use of a selective reflector and which has at least a liquid-crystal layer formed by fixing the cholesteric liquid-crystal phase of the selective reflector, wherein the selective reflector comprises a film comprising a support and, as formed on the support, a liquid-crystal layer in which a cholesteric liquid-crystal phase formed by polymerizing s cholesteric liquid-crystal mixture is fixed, 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), a fluorine-containing horizontal alignment agent and a polymerization initiator:

Z¹—

Y¹-A¹-Y³-M¹-Y⁴-A²-Y²—

Z² 

 

General Formula (Ia)

Z³—

Y⁵-A³-Y⁷-M²-P 

 

General Formula (Ib)

wherein, in the general formulae (Ia) and (Ib), Z¹, Z² and Z³ each independently represent a polymerizable group;

A¹, A² and A³ each independently represent a spacer having an atom-bonding chain length of from 1 to 30, provided that the spacer represents an alkylene group, or a linking group of multiple alkylene groups bonding to each other via —

O—

or —

CO—

;

M¹ and M² each independently represent (-T¹-Y⁸)_n-T²-;

n indicates a natural number;

when n is 2 or more, then multiple (-T¹-Y⁸)'"'"'s may be the same or different;

T¹ and T² each independently represent a saturated or unsaturated hydrocarbon ring, or a saturated or unsaturated hetero ring, provided that the hydrocarbon ring and the hetero ring may have a substituent;

Y¹, Y², Y³, Y⁴, Y⁵, Y⁷ and Y⁸ each independently represent a single bond, —

O—

, —

CO—

, —

O—

CO—

, —

CO—

O—

or —

O—

CO—

O—

;

P represents a hydrogen atom or an alkyl group having from 1 to 15 carbon atoms.

14. A laminated glass comprising a laminate and at least two glass sheets, wherein:

the laminate is sandwiched between the two glass sheets,

the laminate is formed by the use of a selective reflector and has at least a liquid-crystal layer formed by fixing the cholesteric liquid-crystal phase of the selective reflector, and

the selective reflector comprises a film comprising a support and, as formed on the support, a liquid-crystal layer in which a cholesteric liquid-crystal phase formed by polymerizing s cholesteric liquid-crystal mixture is fixed, 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), a fluorine-containing horizontal alignment agent and a polymerization initiator;

Z¹—

Y¹-A¹-Y³-M¹-Y⁴-A²-Y²—

Z² 

 

General Formula (Ia)

Z³—

Y⁵-A³-Y⁷-M²-P 

 

General Formula (Ib)

wherein, in the general formulae (Ia) and (Ib), Z¹, Z² and Z³ each independently represent a polymerizable group;

A¹, A² and A³ each independently represent a spacer having an atom-bonding chain length of from 1 to 30, provided that the spacer represents an alkylene group, or a linking group of multiple alkylene groups bonding to each other via —

O—

or —

CO—

;

M¹ and M² each independently represent (-T¹-Y⁸)_n-T²-;

n indicates a natural number;

when n is 2 or more, then multiple (-T¹-Y⁸)'"'"'s may be the same or different;

T¹ and T² each independently represent a saturated or unsaturated hydrocarbon ring, or a saturated or unsaturated hetero ring, provided that the hydrocarbon ring and the hetero ring may have a substituent;

Y¹, Y², Y³, Y⁴, Y⁵, Y⁷ and Y⁸ each independently represent a single bond, —

O—

, —

CO—

, —

O—

CO—

, —

CO—

O—

or —

O—

CO—

O—

;

P represents a hydrogen atom or an alkyl group having from 1 to 15 carbon atoms.

15. A windshield for automobiles, comprising a laminate glass comprising a laminate and at least two glass sheets, wherein:

the laminate is sandwiched between the two glass sheets,

the laminate is formed by the use of a selective reflector and has at least a liquid-crystal layer formed by fixing the cholesteric liquid-crystal phase of the selective reflector, and

the selective reflector comprises a film comprising a support and, as formed on the support, a liquid-crystal layer in which a cholesteric liquid-crystal phase formed by polymerizing s cholesteric liquid-crystal mixture is fixed, 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), a fluorine-containing horizontal alignment agent and a polymerization initiator;

Z¹—

Y¹-A¹-Y³-M¹-Y⁴-A²-Y²—

Z² 

 

General Formula (Ia)

Z³—

Y⁵-A³-Y⁷-M²-P 

 

General Formula (Ib)

wherein, in the general formulae (Ia) and (Ib), Z¹, Z² and Z³ each independently represent a polymerizable group;

A¹, A² and A³ each independently represent a spacer having an atom-bonding chain length of from 1 to 30, provided that the spacer represents an alkylene group, or a linking group of multiple alkylene groups bonding to each other via —

O—

or —

CO—

;

M¹ and M² each independently represent (-T¹-Y⁸)_n-T²-;

n indicates a natural number;

when n is 2 or more, then multiple (-T¹-Y⁸)'"'"'s may be the same or different;

T¹ and T² each independently represent a saturated or unsaturated hydrocarbon ring, or a saturated or unsaturated hetero ring, provided that the hydrocarbon ring and the hetero ring may have a substituent;

Y¹, Y², Y³, Y⁴, Y⁵, Y⁷ and Y⁸ each independently represent a single bond, —

O—

, —

CO—

, —

O—

CO—

, —

CO—

O—

or —

O—

CO—

O—

;

P represents a hydrogen atom or an alkyl group having from 1 to 15 carbon atoms.

16. Glass for building materials, comprising a laminate glass comprising a laminate and at least two glass sheets, wherein:

the laminate is sandwiched between the two glass sheets,

the laminate is formed by the use of a selective reflector and has at least a liquid-crystal layer formed by fixing the cholesteric liquid-crystal phase of the selective reflector, and

the selective reflector comprises a film comprising a support and, as formed on the support, a liquid-crystal layer in which a cholesteric liquid-crystal phase formed by polymerizing s cholesteric liquid-crystal mixture is fixed, 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), a fluorine-containing horizontal alignment agent and a polymerization initiator;

Z¹—

Y¹-A¹-Y³-M¹-Y⁴-A²-Y²—

Z² 

 

General Formula (Ia)

Z³—

Y⁵-A³-Y⁷-M²-P 

 

General Formula (Ib)

wherein, in the general formulae (Ia) and (Ib), Z¹, Z² and Z³ each independently represent a polymerizable group;

A¹, A² and A³ each independently represent a spacer having an atom-bonding chain length of from 1 to 30, provided that the spacer represents an alkylene group, or a linking group of multiple alkylene groups bonding to each other via —

O—

or —

CO—

;

M¹ and M² each independently represent (-T¹-Y⁸)_n-T²-;

n indicates a natural number;

when n is 2 or more, then multiple (-T¹-Y⁸)'"'"'s may be the same or different;

T¹ and T² each independently represent a saturated or unsaturated hydrocarbon ring, or a saturated or unsaturated hetero ring, provided that the hydrocarbon ring and the hetero ring may have a substituent;

Y¹, Y², Y³, Y⁴, Y⁵, Y⁷ and Y⁸ each independently represent a single bond, —

O—

, —

CO—

, —

O—

CO—

, —

CO—

O—

or —

O—

CO—

O—

;

P represents a hydrogen atom or an alkyl group having from 1 to 15 carbon atoms.