# US 2014/0192286 A1 · Cholesteric liquid crystal mixture, film, selective reflective plate, laminate, laminated glass

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- Number: US 2014/0192286 A1
- Document ID: US20140192286A1
- Status: Published application
- Kind: A1
- Application number: 14/204,822
- Filed: 2014-03-11
- Published: 2014-07-10
- Earliest claimed: 2011-09-12
- Assignees: FUJIFILM Corporation
- Applicants: Fujifilm Corporation
- Inventors: Tomoki TASAKA; Yasuhiro ISHIWATA; Minoru UEMURA; Takao TAGUCHI; Masao NAKAJIMA; Shunya KATOH
- Web page: https://patentgrep.com/patent/US20140192286A1

## CPC

- C09K 19/56: Aligning agents
- B32B 17/10036: {comprising two outer glass sheets}
- B32B 17/10293: {Edge features, e.g. inserts or holes}
- B32B 17/10504: {Liquid crystal layer}
- B32B 17/10761: {containing vinyl acetal}
- B60J 3/04: adjustable in transparency
- C09K 19/2007: {the chain containing -COO- or -OCO- groups}
- G02B 5/208: {for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation}
- 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)}
- C09K 2019/0448: {the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate}
- C09K 2019/2078: {Ph-COO-Ph-COO-Ph}
- G02F 2201/343: cholesteric liquid crystal reflector
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B60J: WINDOWS, WINDSCREENS, NON-FIXED ROOFS, DOORS, OR SIMILAR DEVICES FOR VEHICLES; REMOVABLE EXTERNAL PROTECTIVE COVERINGS SPECIALLY ADAPTED FOR VEHICLES (fastening, suspending, closing, or opening of such devices E05)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS

## 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

### Claim 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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.

### Claim 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.

### Claim 7 (depends on 6)

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

### Claim 8 (depends on 6)

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

### Claim 9 (depends on 6)

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

### Claim 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.

### Claim 11 (depends on 10)

The selective reflector according to claim 10, containing a λ/2 plate.

### Claim 12 (depends on 10)

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

### Claim 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.

### Claim 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.

### Claim 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.

### Claim 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.