# US 9,518,222 B2 · Liquid crystal compound, liquid crystal composition and liquid crystal display device

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- Number: US 9,518,222 B2
- Document ID: US9518222B2
- Status: Granted
- Kind: B2
- Application number: 14/820,229
- Filed: 2015-08-06
- Published: 2016-02-18
- Granted: 2016-12-13
- Earliest claimed: 2014-08-06
- Assignees: Jnc Corporation; Jnc Petrochemical Corporation
- Applicants: Jnc Corporation; Jnc Petrochemical Corporation
- Inventors: Mayumi Goto; Hiroyuki Tanaka
- Web page: https://patentgrep.com/patent/US9518222B2

## CPC

- C09K 19/322: {Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring}
- C07C 43/225: containing halogen
- C07C 255/54: containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
- C07D 213/30: Oxygen atoms
- C07D 239/26: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 239/34: One oxygen atom
- C07D 309/06: Radicals substituted by oxygen atoms
- C07D 319/06: not condensed with other rings
- C07D 493/08: Bridged systems
- C09K 19/20: linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters {or ethers}
- C09K 19/3066: {in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers}
- C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K 19/3458: {Uncondensed pyrimidines}
- C09K 2019/0466: {the linking chain being a -CF2O- chain}
- C09K 2019/3009: {Cy-Ph}
- C09K 2019/3016: {Cy-Ph-Ph}
- C09K 2019/3025: {Cy-Ph-Ph-Ph}
- C09K 2019/323: {containing a binaphthyl}
- C09K 2019/3422: {the heterocyclic ring being a six-membered ring}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

To provide a liquid crystal compound satisfying at least one physical property such as high stability to light, a high clearing point, low minimum temperature of a liquid crystal phase, small viscosity, suitable optical anisotropy, large dielectric anisotropy, large dielectric constant in a minor-axis direction, suitable elastic constant, excellent compatibility, a liquid crystal composition containing the compound and a liquid crystal display device including the composition. The compound is represented by formula (1): wherein, for example, R1 is alkyl having 1 to 15 carbons, rings A1 to A4 are 1,4-cyclohexylene or 1,4-phenylene, at least one of Z1 to Z5 is —CF2O—, and X1 is fluorine or —OCF3; W1 is a group represented by formula (1a) or (1b); wherein, Y1 to Y5 are fluorine; W2 is a group represented by formula (1c) or (1d); wherein, L1 to L5 are fluorine; and a, b, c and d are independently 0 or 1.

## Claims

### Claim 1

A compound represented by formula (1):
wherein, in formula (1),
R1 is alkyl having 1 to 15 carbons, in the alkyl, at least one of —CH2— may be replaced by —O— or —S—, at least one of —(CH2)2— may be replaced by —CH═CH—, and in the groups, at least one of hydrogen may be replaced by halogen;
ring A1, ring A2, ring A3 and ring A4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, chroman-2,6-diyl, 2,3-dihydro-1H-indene-2,5-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and at least one of hydrogen directly bonded with the above rings may be replaced by halogen;
W1 is a group represented by formula (1a) or formula (1b);
wherein, in formula (1a) and formula (1b),
Y1 and Y2 are independently fluorine or chlorine, Y3, Y4 and Y5 are independently hydrogen, fluorine or chlorine, and at least two of Y3, Y4 and Y5 is fluorine or chlorine; and
in formula (1),
W2 is a group represented by formula (1c) or formula (1d);
wherein, in formula (1c) and formula (1d),
L1, L2, L3, L4 and L5 are independently hydrogen, fluorine or chlorine; and
in formula (1),
when W1 is represented by formula (1a) and W2 is represented by formula (1c), at least one of ring A1, ring A2, ring A3 and ring A4 is naphthalene-2,6-diyl in which at least one of hydrogen may be replaced by halogen;
X1 is fluorine, —C≡N, —N═C═S or alkyl having 1 to 10 carbons in which at least one of hydrogen is replaced by fluorine, alkenyl having 2 to 10 carbons in which at least one of hydrogen is replaced by fluorine, alkoxy having 1 to 9 carbons in which at least one of hydrogen was replaced by fluorine, or alkenyloxy having 2 to 9 carbons in which at least one of hydrogen is replaced by fluorine;
a, b, c and d are independently 0 or 1, and a sum of a, b, c and d is 0, 1, 2 or 3;
Z1, Z2, Z3, Z4 and Z5 are independently a single bond or alkylene having 1-6 carbons, in the alkylene, at least one of —CH2— may be replaced by —O—, —S—, —CO— or —SiH2—, one or two of —CH2CH2— may be replaced by —CH═CH— or —C≡C—, and in the divalent groups, at least one of hydrogen may be replaced by fluorine or chlorine; and
at least one of Z1 in the case where a is 1, Z2 in the case where b is 1, Z3 in the case where c is 1, Z4 in the case where d is 1, and Z5 is —CF2O—.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein, in formula (1) described in claim 1,
R1 is alkyl having 1 to 15 carbons, alkenyl having 2 to 15 carbons, alkoxy having 1 to 14 carbons or alkenyloxy having 2 to 14 carbons, and in the groups, at least one of hydrogen may be replaced by fluorine;
X1 is fluorine, —C≡N, —N═C═S, —CHF, —CHF2, —CF3, —(CH2)2—F, —CH2CF3, —CF2CF3, —(CH2)3—F, —(CH2)2—CF3, —(CF2)3—F, —(CH2)4—F, —(CH2)3—CF3, —(CF2)4—F, —(CF2)5—F, —(CF2)6—F, —(CF2)7—F, —OCH2F, —OCHF2, —OCF3, —O—(CH2)2—F, —OCH2CF3, —OCF2CF3, —O—(CH2)3—F, —O—(CH2)2—CF3, —O—(CF2)3—F, —O(CH2)4—F, —O—(CH2)3—CF3, —O—(CF2)4—F, —O—(CF2)5—F, —O—(CF2)6—F, —CH═CHF, —CH═CF2, —CF═CHF, —CF═CF2, —CH═CHCH2F, —CH═CHCF3, —CF═CHCF3, —CF═CFCF3, —(CH2)2—CH═CF2, —(CH2)2—CF═CF2, —(CH2)2—CH═CHCF3, —(CH2)2—CF═CHCF3 or —(CH2)2—CF═CFCF3; and
Z1, Z2, Z3, Z4 and Z5 are independently a single bond, —(CH2)2—, —(CH2)4—, —COO—, —OCO—, —CH2O—, —OCH2—, —CF2O—, —OCF2—, —CH═CH—, —CF═CF—, —C≡C—, —(CH2)2COO—, —OCO(CH2)2—, —(CH2)2CF2O—, —OCF2(CH2)2—, —(CH2)3O— or —O(CH2)3—.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein, in formula (1) described in claim 1,
R1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyloxy having 2 to 9 carbons, and in the groups, at least one of hydrogen may be replaced by fluorine; and
X1 is fluorine, —C≡N, —CF3, —CHF2, —OCF3, —OCHF2, —CH═CHCF3, —CF═CHCF3 or —CF═CFCF3.

### Claim 4 (depends on 1)

The compound according to claim 1, represented by any one of formulas (1-1) to (1-8):
wherein, in formulas (1-1) to (1-8),
R1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy 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 of hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, naphthalene-2,6-diyl, or naphthalene-2,6-diyl in which at least one of hydrogen is replaced by fluorine;
W1 is a group represented by formula (1a) or formula (1b);
wherein, in formula (1a) and formula (1b),
Y1 and Y2 are fluorine, Y3, Y4 and Y5 are independently hydrogen or fluorine, and at least two of Y3, Y4 and Y5 is fluorine; and
in formulas (1-1) to (1-8),
W2 is a group represented by formula (1c) or formula (1d);
wherein, in formula (1c) and formula (1d),
L1, L2, L3, L4 and L5 are independently hydrogen or fluorine; and
in formulas (1-1) to (1-8),
when W1 is represented by formula (1a) and W2 is represented by formula (1c), at least one of ring A1, ring A2, ring A3 and ring A4 is naphthalene-2,6-diyl in which at least one of hydrogen may be replaced by halogen;
Z1, Z2, Z3, Z4 and Z5 are independently a single bond, —(CH2)2—, —(CH2)4—, —COO—, —OCO—, —CH2O—, —OCH2—, —CF2O—, —OCF2—, —CH═CH—, —CF═CF—, —C≡C—, —(CH2)2COO—, —OCO(CH2)2—, —(CH2)2CF2O—, —OCF2(CH2)2—, —(CH2)3O— or —O(CH2)3—, and at least one of Z1, Z2, Z3, Z4 and Z5 is —CF2O—; and
X1 is fluorine, —CF3, —CHF2, —OCF3 or —OCHF2.

### Claim 5 (depends on 1)

The compound according to claim 1, represented by any one of formulas (1-9) to (1-29):
wherein, in formulas (1-9) to (1-29),
R1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons;
ring A1, ring A2 and ring A3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, naphthalene-2,6-diyl, or naphthalene-2,6-diyl in which at least one of hydrogen is replaced by fluorine;
Z1, Z2, Z3 and Z5 are independently a single bond, —(CH2)2—, —(CH2)4—, —COO—, —OCO—, —CH2O—, —OCH2—, —CF2O—, —OCF2—, and at least one of Z1, Z2, Z3 and Z5 is —CF2O—;
X1 is fluorine, —CF3 or —OCF3; and
L1, L2, L3, L4, L5, L6, L7, L8, Y1, Y2, Y3, Y4 and Y5 are independently hydrogen or fluorine.

### Claim 6 (depends on 1)

The compound according to claim 1, represented by any one of formulas (1-30) to (1-54):
wherein, in formulas (1-30) to (1-54),
R1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons;
ring A1, ring A2 and ring A3 are independently 1,4-cyclohexylene, 1,4-yclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, naphthalene-2,6-diyl, or naphthalene-2,6-diyl in which at least one of hydrogen is replaced by fluorine;
Z1, Z2, Z3 and Z5 are independently a single bond, —(CH2)2—, —COO—, —OCO—, —CH2O—, —OCH2—, —CF2O— and —OCF2—;
X1 is fluorine, —CF3 or —OCF3; and
L1, L2, L3, L4, L5, L6, L7, L8 and Y5 are independently hydrogen or fluorine.

### Claim 7 (depends on 1)

The compound according to claim 1, represented by any one of formulas (1-55) to (1-78):
wherein, in formulas (1-55) to (1-78),
R1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons;
X1 is fluorine, —CF3 or —OCF3; and
L2, L3, L5, L6, L7, L8 and Y5 are hydrogen or fluorine.

### Claim 8 (depends on 1)

The compound according to claim 1, represented by any one of formulas (1-79) to (1-98):
wherein, in formulas (1-79) to (1-98),
R1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons;
X1 is fluorine, —CF3 or —OCF3; and
L2 and L5 are hydrogen or fluorine.

### 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 (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 of hydrogen may be replaced by fluorine and at least one 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, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 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 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 formula (5):
wherein, in formula (5),
R12 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of hydrogen may be replaced by fluorine and at least one of —CH2— may be replaced by —O—;
X12 is —C≡N or —C≡C—C≡N;
ring C1 is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;
Z14 is a single bond, —CH2CH2—, —C≡C—, —COO—, —CF2O—, —OCF2— or —CH2O—;
L13 and L14 are independently hydrogen or fluorine; and
i is 1, 2, 3 or 4.

### Claim 12 (depends on 9)

The liquid crystal composition according 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 and R14 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 of —CH2— may be replaced by —O—;
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 of —CH2— may be replaced by —O— and at least one 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 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—, —COO—, —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, a sum of q, r and s is 0, 1, 2 or 3, and t is independently 1, 2 or 3.

### Claim 13 (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 or the alkenyl, at least one of —CH2— may be replaced by —O— and at least one 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 14 (depends on 9)

The liquid crystal composition according to claim 9, further containing at least one of a polymerizable compound, an optically active compound, an antioxidant, an ultraviolet light absorber, a light stabilizer, a heat stabilizer and an antifoaming agent.

### Claim 15 (depends on 9)

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