# US 10,308,871 B2 · Liquid crystal compound having benzothiophene, liquid crystal composition and liquid crystal display device

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- Number: US 10,308,871 B2
- Document ID: US10308871B2
- Status: Granted
- Kind: B2
- Application number: 15/547,063
- Filed: 2016-02-10
- Published: 2018-01-18
- Granted: 2019-06-04
- Earliest claimed: 2015-02-19
- Assignees: Jnc Corporation; Jnc Petrochemical Corporation
- Applicants: Jnc Corporation; Jnc Petrochemical Corporation
- Inventors: Tomohiro Yano
- Web page: https://patentgrep.com/patent/US10308871B2

## CPC

- C09K 19/3491: {having sulfur as hetero atom}
- C07D 333/54: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D 333/56: Radicals substituted by oxygen atoms
- C07D 333/64: Oxygen atoms
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/08: linked by a carbon chain containing alicyclic rings
- C07D 409/10: linked by a carbon chain containing aromatic rings
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C09K 19/30: containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K 19/34: containing at least one heterocyclic ring
- C09K 19/42: Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K 19/54: Additives having no specific mesophase {characterised by their chemical composition}
- C09K 19/542: {Macromolecular compounds}
- C09K 19/586: {Optically active dopants; chiral dopants}
- G02F 1/13: based on liquid crystals, e.g. single liquid crystal display cells
- C09K 2019/548: {stabilizing the alignment; Polymer stabilized alignment}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

Provided is a liquid crystal compound that has high stability to heat, light and so forth, a high clearing point, low minimum temperature of a liquid crystal phase, small viscosity, suitable optical anisotropy, large negative dielectric anisotropy, a suitable elastic constant and excellent compatibility with other liquid crystal compounds, a liquid crystal composition containing the compound and a liquid crystal display device including the composition. The compound is represented by formula (1). For example, R1 is alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyl having 2 to 10 carbons; R2 is alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyl having 3 to 10 carbons; ring A1 is 1,4-cyclohexylene or 1,4-phenylene; ring A2 is 1,4-cyclohexylene or 1,4-phenylene; Z1 and Z2 are a single bond; Z3 is —O— or a single bond; and L1 is F, CF3 or CF2H.

## Claims

### Claim 1

A compound, represented by formula (1):
wherein, in formula (1),
R1 and R2 are independently hydrogen, halogen or alkyl having 1 to 20 carbons, and in the alkyl, at least one piece of —CH2— may be replaced by —O— or —S—, at least one piece of —(CH2)2— may replace by —CH═CH—, and in the groups, at least one piece of hydrogen may be replaced by halogen;
ring A1 and ring A2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, or pyridine-2,5-diyl, and at least one piece of hydrogen on the rings may be replaced by halogen;
Z1 and Z2 are independently a single bond or alkylene having 1 to 4 carbons, in the alkylene, at least one piece of —CH2— may be replaced by —O— or —COO—, and at least one piece of —(CH2)2— may replace by —CH=CH— or —C≡C—, and in the groups, at least one piece of hydrogen may be replaced by halogen;
Z3 is —O— or a single bond;
L1 is F, CF3 or CF2H; and
a and b are independently 0, 1, 2, 3 or 4, and a sum of a and b is 4 or less, and when a or b is 2 or more, two of arbitrary ring A1, two of arbitrary ring A2, two pieces of arbitrary Z1 or two pieces of arbitrary Z2 may be identical or different.

### Claim 2 (depends on 1)

The compound according to claim 1, represented by formula (1-2):
wherein, in formula (1-2),
R1 and R2 are independently hydrogen, halogen or alkyl having 1 to 20 carbons, and in the alkyl, at least one piece of —CH2— may be replaced by —O— or —S—, at least one piece of —(CH2)2— may replace by —CH═CH—, and in the groups, at least one piece of hydrogen may be replaced by halogen;
ring A1 and ring A2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, or pyridine-2,5-diyl, and at least one piece of hydrogen on the rings may be replaced by halogen;
Z1 and Z2 are independently a single bond or alkylene having 1 to 4 carbons, in the alkylene, at least one piece of —CH2— may be replaced by —O— or —COO—, and at least one piece of —(CH2)2— may replace by —CH═CH— or and in the groups, at least one piece of hydrogen may be replaced by halogen;
Z3 is —O— or a single bond; and
a and b are independently 0, 1, 2, 3 or 4, and a sum of a and b is 4 or less, and when a or b is 2 or more, two of ring A′ and A2, and two of Z1 and Z2 may be identical or different.

### Claim 3 (depends on 2)

The compound according to claim 2, wherein, in formula (1-2), R1 and R2 are independently chlorine, fluorine, alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkenyl having 2 to 10 carbons, polyfluoroalkyl having 1 to 10 carbons or polyfluoroalkyl having 1 to 9 carbons;
ring A1 and ring A2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one piece of hydrogen may be replaced by halogen, or tetrahydropyran-2,5-diyl;
Z1 and Z2 are independently a single bond, —(CH2)2—, —CH═CH—, —CF═CF—, —COO—, —OCO—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —(CH2)4—, —(CH2)2CF2O—, —(CH2)2OCF2-5—CF2O(CH2)2—, —OCF2 (CH2)2—CH═CH—(CH2)2— or —(CH2)2—CH═CH—; and
a and b are independently 0, 1, 2, 3 or 4, and a sum of a and b is 4 or less.

### Claim 4 (depends on 2)

The compound according to claim 2, wherein, in formula (1-2), a sum of a and b is 0, 1, 2 or 3;
R1 and R2 are independently chlorine, fluorine, alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkenyl having 2 to 10 carbons, polyfluoroalkyl having 1 to 10 carbons or polyfluoroalkyl having 1 to 9 carbons;
ring A1 and ring A2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one piece of hydrogen may be replaced by halogen, tetrahydropyran-2,5-diyl; and
Z1 and Z2 are independently a single bond, —(CH2)2—, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —(CH2)4—, —(CH2)2CF2O—, —(CH2)2OCF2—CF2O(CH2)2—, —OCF2 (CH2)2—CH═CH—(CH2)2— or —(CH2)2—CH═CH—.

### Claim 5 (depends on 1)

The compound according to claim 1, represented by any one of formulas (1-2-1) to (1-2-10):
wherein, in formulas (1-2-1) to (1-2-10), R1 and R2 are independently chlorine, fluorine, alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkenyl having 2 to 10 carbons, polyfluoroalkyl having 1 to 10 carbons or polyfluoroalkyl having 1 to 9 carbons;
ring A1, ring A2, ring A3 and ring A4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one piece of hydrogen is replaced by halogen, or tetrahydropyran-2,5-diyl; and
Z1, Z2, Z4 and Z5 are independently a single bond, —(CH2)2—CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —(CH2)4—, —(CH2)2CF2O—, —(CH2)2OCF2—CF2O(CH2)2—, —OCF2 (CH2)2—CH═CH—(CH2)2— or —(CH2)2—CH═CH—.

### Claim 6 (depends on 5)

The compound according to claim 5, wherein, in formulas (1-2-1) to (1-2-10), R1 and R2 are independently fluorine, alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkenyl having 2 to 10 carbons or polyfluoroalkyl having 1 to 9 carbons;
ring A1, ring A2, ring A3 and ring A4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one piece of hydrogen may be replaced by halogen, or tetrahydropyran-2,5-diyl; and
Z1, Z2, Z4 and Z5 are independently a single bond, —(CH2)2—CH═CH—, —CF2O—, —OCF2—, —CH2O— or —OCH2—.

### Claim 7 (depends on 6)

The compound according to claim 6, represented by any one of formulas (1-2-4), (1-2-7) and (1-2-9):

### Claim 8 (depends on 6)

The compound according to claim 6, represented by any one of formulas (1-2-1), (1-2-5), (1-2-8) and (1-2-10), wherein, R1 is alkoxy having 1 to 6 carbons:

### Claim 9 (depends on 1)

A liquid crystal composition, containing at least one compound according to claim 1.

### Claim 10 (depends on 9)

The liquid crystal composition according to claim 9, further containing at least one compound selected from the group of compounds represented by formulas (6) to (12):
wherein in formulas (6) to (12),
R13 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH2— may be replaced by —O—, and at least one piece of hydrogen may be replaced by fluorine;
R14 is alkyl having 1 to 10 carbons, in the alkyl, at least one piece of —CH2— may be replaced by —O—, and at least one piece of hydrogen may be replaced by fluorine;
R15 is hydrogen, fluorine, alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH2— may be replaced by —O—, and at least one piece of hydrogen may be replaced by fluorine;
S11 is hydrogen or methyl;
X is —CF2—, —O— or —CHF—;
ring D1, ring D2, ring D3 and ring D4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one piece of hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl;
ring D5 and ring D6 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl;
Z15, Z16, Z17 and Z18 are independently a single bond, —CH2CH2—, —OCO—, —CH2O—, —OCF2— or —OCF2CH2CH2—;
L15 and L16 are independently fluorine or chlorine; and
j, k, m, n, p, q, r and s are independently 0 or 1, a sum of k, m, n and p is 1 or 2, and a sum of q, r and s is 0, 1, 2 or 3, and t is 1, 2 or 3.

### Claim 11 (depends on 9)

The liquid crystal composition according to claim 9, further containing at least one compound selected from the group of compounds represented by formulas (13) to (15):
wherein in formulas (13) to (15),
R16 and R17 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH2— may be replaced by —O—, and at least one piece of hydrogen may be replaced by fluorine;
ring E1, ring E2, ring E3 and ring E4 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene or pyrimidine-2,5-diyl; and
Z19, Z20 and Z21 are independently a single bond, —CH2CH2—, —CH—CH—, —C≡C— or —COO—.

### Claim 12 (depends on 9)

The liquid crystal composition according to claim 9, further containing at least one compound selected from the group of compounds represented by formulas (2) to (4):
wherein in formulas (2) to (4),
R11 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of hydrogen may be replaced by fluorine, and at least one piece of —CH2— may be replaced by —O—;
X11 is fluorine, chlorine, —OCF3, —OCHF2, —CF3, —CHF2, —CH2F, —OCF2CHF2 or —OCF2CHFCF3;
ring B1, ring B2 and ring B3 are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one piece of hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl;
Z11, Z12 and Z13 are independently a single bond, —CH2CH2—, —CH═CH—, —C≡C—, —COO—, —CF2O—, —OCF2—, —CH2O— or —(CH2)4—; and
L11 and L12 are independently hydrogen or fluorine.

### Claim 13 (depends on 9)

The liquid crystal composition according to claim 9, further containing at least one optically active compound and/or at least one polymerizable compound.

### Claim 14 (depends on 9)

The liquid crystal composition according to claim 9, further containing at least one antioxidant and/or at least one ultraviolet light absorbent.

### Claim 15 (depends on 9)

A liquid crystal display device, including the liquid crystal composition according to claim 9.

### Claim 16 (depends on 9)

A liquid crystal display device, wherein the liquid crystal composition according to claim 9 is encapsulated.