# US 10,308,870 B2 · Liquid crystal medium, optical device and liquid crystal compound

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- Number: US 10,308,870 B2
- Document ID: US10308870B2
- Status: Granted
- Kind: B2
- Application number: 15/100,979
- Filed: 2014-12-04
- Published: 2016-10-20
- Granted: 2019-06-04
- Earliest claimed: 2013-12-10
- Assignees: Jnc Corporation; Jnc Petrochemical Corporation
- Applicants: Jnc Corporation; Jnc Petrochemical Corporation
- Inventors: Yasuhiro Haseba; Koki Sago; Shinichi Yamamoto
- Web page: https://patentgrep.com/patent/US10308870B2

## CPC

- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- C07C 43/225: containing halogen
- C09K 19/20: linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters {or ethers}
- C09K 19/3444: {the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine}
- C09K 19/3458: {Uncondensed pyrimidines}
- C09K 19/56: Aligning agents
- C09K 19/586: {Optically active dopants; chiral dopants}
- C09K 19/588: {Heterocyclic compounds}
- C09K 2019/0466: {the linking chain being a -CF2O- chain}
- C09K 2019/3422: {the heterocyclic ring being a six-membered ring}
- G02F 1/134309: {characterised by their geometrical arrangement}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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 liquid crystal medium that has stability to heat, light and so forth, a wide temperature range of a liquid crystal phase and significantly large dielectric anisotropy to develop an optically isotropic liquid crystal phase is required. Moreover, various optical devices that can be used in a wide temperature range, and have a short response time, a large contrast ratio and a low drive voltage are required. A liquid crystal composition contains an achiral component T containing at least one compound (1) represented by formula (1) and a chiral agent to develop an optically isotropic liquid crystal phase, wherein in formula (1), R1 is alkyl having 1 to 12 carbons, L1, L2 and L3 are each independently hydrogen, fluorine or chlorine; and Y1 is fluorine, CF3, or —OCF3.

## Claims

### Claim 1

A liquid crystal composition that contains an achiral component T containing at least one compound (1) represented by formula (1) as a first component and a chiral agent containing at least one compound represented by formulas (K6) to (K7) to develop an optically isotropic liquid crystal phase:
wherein, in formula (1), R1 is hydrogen, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkynyl having 2 to 12 carbons or alkoxy having 1 to 11 carbons; L1 is fluorine, L2 is hydrogen and L3 is fluorine; and Y1 is fluorine, CF3 or —OCF3;
wherein, in the formulas, RK is each independently hydrogen, halogen, —C≡N, —N═C═O, —N═C═S or alkyl having 1 to 12 carbons, at least one piece of —CH2— in RK may be replaced by —O—, —S—, —COO— or —OCO—, at least one piece of —CH2—CH2— in RK may be replaced by —CH═CH—, —CF═CF— or and at least one piece of hydrogen in RK may be replaced by fluorine or chlorine;
AK is each independently an aromatic 6-membered to 8-membered ring, a non-aromatic 3-membered to 8-membered ring or a condensed ring having 9 or more carbons, and at least one piece of hydrogen of the rings may be replaced by halogen, alkyl or haloalkyl having 1 to 3 carbons, —CH2— of the rings may be replaced by —O—, —S— or —NH—, and —CH═ may be replaced by —N═;
ZK is each independently a single bond or alkylene having 1 to 8 carbons, at least one piece of —CH2— in ZK may be replaced by —O—, —S—, —COO—, —OCO—, —CSO—, —OCS—, —CH═N— or —N═CH—, at least one piece of —CH2—CH2— in ZK may be replaced by —CH═CH—, —CF═CF— or and at least one piece of hydrogen of ZK may be replaced by halogen;
XK is each independently a single bond, —COO—, —OCO—, —CH2O—, —OCH2—, —OCF2— or —CH2CH2—; and
mK is each independently an integer from 1 to 3.

### Claim 2 (depends on 1)

The liquid crystal composition according to claim 1, further containing at least one of compound (3) represented by formula (3) or compound (7) represented by formula (7) as a second component of the achiral component T:
wherein, in formula (3), R3 is hydrogen or alkyl having 1 to 12 carbons, at least one piece of —CH2— in R3 may be replaced by —O—, —S—, —COO— or —OCO—, at least one piece of —CH2—CH2— in R3 may be replaced by —CH═CH—, —CF═CF— or —C≡C—, and at least one piece of hydrogen in R3 may be replaced by fluorine or chlorine, however, in R3, a case where —O— and —CH═CH— are adjacent is excluded, and a case where —CO— and —CH═CH— are adjacent is excluded;
Z31, Z32, Z33 and Z34 are each independently a single bond or alkylene having 1 to 4 carbons, and at least one piece of —CH2— in the alkylene may be replaced by —O—, —COO— or —CF2O—;
L31, L32, L33, L34, L35 and L36 are each independently hydrogen or fluorine;
X3 is hydrogen, halogen, —SF5 or alkyl having 1 to 10 carbons, at least one piece of —CH2— in X3 may be replaced by —O—, —S—, —COO— or —OCO—, at least one piece of —CH2—CH2— in X3 may be replaced by —CH═CH—, —CF═CF— or —C≡C—, and at least one piece of hydrogen in X3 may be replaced by fluorine or chlorine, however, in X3, a case where —O— and —CH═CH— are adjacent is excluded, and a case where —CO— and —CH═CH— are adjacent is excluded;
n31 and n32 are each independently 0 or 1;
however, when n31+n32=1 and Z33 is CF2O, both L35 and L36 are fluorine;
wherein, in formula (7), R7 is hydrogen or alkyl having 1 to 12 carbons, at least one piece of —CH2— in R7 may be replaced by —O—, —S—, —COO— or —OCO—, at least one piece of —CH2—CH2— in R7 may be replaced by —CH═CH—, —CF═CF— or —C≡C—, and at least one piece of hydrogen in R7 may be replaced by fluorine or chlorine, however, in R7, a case where —O— and —CH═CH— are adjacent is excluded, and a case where —CO— and —CH═CH— are adjacent is excluded;
L71, L72, L73, L74, L75, L76, L77 and L78 are each independently hydrogen or fluorine;
Z71, Z72 and Z73 are each independently a single bond, —COO— or —CF2O—;
n71 and n72 are each independently 0 or 1; and
X7 is hydrogen, halogen, —SF5 or alkyl having 1 to 10 carbons, at least one piece of —CH2— in X7 may be replaced by —O—, —S—, —COO— or —OCO—, at least one piece of —CH2—CH2— in X7 may be replaced by —CH═CH—, —CF═CF— or —C≡C—, at least one piece of hydrogen in X7 may be replaced by fluorine or chlorine, however, in X7, a case where —O— and —CH═CH— are adjacent is excluded, and a case where —CO— and —CH═CH— are adjacent is excluded.

### Claim 3 (depends on 2)

The liquid crystal composition according to claim 2, wherein compound (3) is a compound represented by any one of formula (3-2) or (3-3):
wherein, in the formulas, R3A is each independently alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkoxy having 1 to 11 carbons;
L31, L32, L33, L34 and L35 are each independently hydrogen or fluorine; and X3A is fluorine, chlorine, —CF3 or —OCF3.

### Claim 4 (depends on 2)

The liquid crystal composition according to claim 2, wherein compound (7) is a compound represented by any one of formulas (7-1) to (7-8):
wherein, in the formulas, R7A is each independently hydrogen, alkyl having 1 to 12 carbons or alkenyl having 2 to 12 carbons or alkoxy having 1 to 11 carbons;
L72, L74, L75, L76, L77 and L78 are each independently hydrogen or fluorine;
X7A is each independently fluorine, chlorine, —CF3 or —OCF3, and
Z71 and Z72 are each independently a single bond, —COO— or —CF2O—, but at least one thereof is —COO— or —CF2O—.

### Claim 5 (depends on 2)

The liquid crystal composition according to claim 2, wherein compound (7) is a compound represented by any one of formulas (7-2-2-E), (7-2-5-E), (7-2-7-E), (7-2-2-F), (7-2-5-F), (7-2-6-F) or (7-2-7-F):
wherein, in the formulas, R7A is each independently alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkoxy having 1 to 11 carbons; and
X7A is fluorine, chlorine, —CF3 or —OCF3.

### Claim 6 (depends on 2)

The liquid crystal composition according to claim 2, containing 20% by weight to 60% by weight of compound (3) in total or 30% by weight to 70% by weight of compound (7) in total, in addition to 10% by weight to 30% by weight of compound (1) in total, based on the total weight of the achiral component T.

### Claim 7 (depends on 1)

The liquid crystal composition according to claim 1, further containing at least one of compound (4) represented by formula (4) and compound (2) represented by formula (2) as a third component of the achiral component T;
wherein, in formula (4), R4 is alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkoxy having 1 to 11 carbons;
B41, B42, B43, and B44 are each independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, 3,5-dichloro-1,4-phenylene or pyrimidine 2,5-diyl;
Z41, Z42, Z43 and Z44 are each independently a single bond, ethylene, —COO—, —OCO—, —CF2O— or —OCF2—;
L48 and L49 are each independently hydrogen or fluorine;
X4 is fluorine, chlorine, —CF3 or —OCF3;
n41 and n42 are each independently 0 or 1;
however, a case where all of B41, B42, B43 and B44 are 1,4-phenylene replaced by fluorine is excluded; and
when n41+n42=1 and Z43 is —CF2O—, both L48 and L49 are fluorine;
wherein, in formula (2), R2 is hydrogen or alkyl having 1 to 12 carbons, at least one piece of —CH2— in R2 may be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, and at least one piece of hydrogen in R2 may be replaced by halogen or alkyl having 1 to 3 carbons;
however, in R2, a case where —O— and —CH═CH— are adjacent is exclude, and a case where —CO— and —CH═CH— are adjacent is excluded;
A21, A22, A23, A24 and A25 are each independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 1,4-phenylene in which one or two pieces of hydrogen are replaced by fluorine, 1,4-phenylene in which two pieces of hydrogen are each replaced by fluorine and chlorine, pyridine-2,5-diyl or pyrimidine-2,5-diyl;
Z21, Z22, Z23, Z24, Z25 and Z26 are each independently a single bond or alkylene having 1 to 4 carbons, and at least one piece of —CH2— in the alkylene may be replaced by —O—, —COO— or —CF2O—;
L21, L22 and L23 are each independently hydrogen or fluorine;
X2 is fluorine, chlorine, —CF3 or —OCF3;
n21, n22, n23, n24 and n25 are each independently 0 or 1, and an expression: 2≤n21+n22+n23+n24+n25≤3 holds,
however, when n21+n22+n23+n24+n25=2, both L22 and L23 are fluorine.

### Claim 8 (depends on 7)

The liquid crystal composition according to claim 7, wherein compound (4) is a compound represented by any one of formulas (4-1) to (4-9):
wherein, in the formulas, R4A is each independently alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkoxy having 1 to 11 carbons;
X4A is fluorine, chlorine, —CF3 or —OCF3; and
L40 to L49 are each independently hydrogen or fluorine.

### Claim 9 (depends on 7)

The liquid crystal composition according to claim 7, wherein compound (2) is a compound represented by any one of formulas (2-1-1-2), (2-1-2-1), (2-1-3-1), (2-1-3-2), (2-1-4-2) or (2-1-4-3):
wherein, in the formulas, R2A is each independently alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkoxy having 1 to 11 carbons;
(F) is each independently hydrogen or fluorine; and
X2A is fluorine chlorine —CF3 or —OCF3.

### Claim 10 (depends on 1)

The liquid crystal composition according to claim 1, exhibiting a chiral nematic phase at any temperature in a temperature range from −20° C. to 70° C., and having 700 nanometers or less in a helical pitch in at least part of the temperature range.

### Claim 11 (depends on 1)

A mixture, containing the liquid crystal composition according to claim 1 and a polymerizable monomer.

### Claim 12 (depends on 11)

A composite material of polymer and liquid crystal, obtained by polymerizing the mixture according to claim 11 and used for a device driven by an optically isotropic liquid crystal phase.