# US 10,310,303 B2 · Liquid crystal compound, liquid crystal composition and liquid crystal display device using the same

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- Number: US 10,310,303 B2
- Document ID: US10310303B2
- Status: Granted
- Kind: B2
- Application number: 15/597,186
- Filed: 2017-05-17
- Published: 2017-11-23
- Granted: 2019-06-04
- Earliest claimed: 2016-05-20
- Assignees: National University Corporation Chiba University; Jnc Corporation; Jnc Petrochemical Corporation
- Applicants: National University Corporation Chiba University; JNC Corporation; JNC Petrochemical Corporation
- Inventors: Keiki Kishikawa; Sang Ho Lee; Yasuyuki Sasada; Tokifumi Masukawa
- Web page: https://patentgrep.com/patent/US10310303B2

## CPC

- G02F 1/133: Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements (arrangements or circuits for control of liquid crystal elements in a matrix, not structurally associated with these elements G09G3/36)
- C09K 19/20: linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters {or ethers}
- C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K 19/322: {Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring}
- C09K 19/44: containing compounds with benzene rings directly linked
- C09K 19/3066: {in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers}
- C09K 2019/0448: {the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate}
- C09K 2019/2042: {Ph-Ph-COO-Ph}
- C09K 2019/2078: {Ph-COO-Ph-COO-Ph}
- C09K 2019/3012: {Cy-Cy-Cy-Ph, or more Cy rings}
- C09K 2019/3021: {Cy-Ph-Ph-Cy}
- 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
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Provided is a liquid crystal compound that can obtain a high-speed response and a sufficient contrast ratio in switching of a display device. A compound represented by formula (1) described below is utilized. In formula (1), ring A is naphthylene, phenantolylene or anthracenylene, and in the groups, at least one piece of hydrogen may be replaced by halogen, —CH3, —C2H5, —CF3, —CHF2, —CH2F, —OCF3, —OCHF2 or —OCH2F; and X1, X2, X3, X4, X5, Y1, Y2, Y3, Y4 and Y5 are independently hydrogen or fluorine, but at least two or more of X1, X2, X3, X4, X5, Y1, Y2, Y3, Y4 and Y5 is fluorine.

## Claims

### Claim 1

A compound, represented by formula (1):
wherein, in formula (1),
ring A is naphthylene, phenanthrenylene, or anthracenylene wherein at least one hydrogen may be replaced by halogen, —CH3, —C2H5, —CF3, —CHF2, —CH2F, —OCF3, —OCHF2, or —OCH2F; and
X1, X2, X3, X4, X5, Y1, Y2, Y3, Y4, and Y5 are independently hydrogen or fluorine, but at least two of X1, X2, X3, X4, X5, Y1, Y2, Y3, Y4, and Y5 are fluorine.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein, in formula (1), ring A is naphthylene, phenanthrenylene, or anthracenylene wherein at least one hydrogen may be independently replaced by fluorine, —CH3, or —CF3.

### Claim 3 (depends on 1)

The compound according to claim 1, represented by any one of formulas (1-1) to (1-12)
wherein, in formulas (1-1) to (1-12),
T1, T2, T3, T4, T5, T6, T7, T8, T9, and T10 are independently hydrogen, halogen, —CH3, —C2H5, —CF3, —CHF2, —CH2F, —OCF3, —OCHF2, or —OCH2F; and
X1, X2, X3, X4, X5, Y1, Y2, Y3, Y4, and Y5 are independently hydrogen or fluorine, but at least two of X1, X2, X3, X4, X5, Y1, Y2, Y3, Y4, and Y5 are fluorine.

### Claim 4 (depends on 3)

The compound according to claim 3, wherein, in formulas (1-1) to (1-12), T1, T2, T3, T4, T5, T6, T7, T8, T9, and T10 are independently hydrogen, fluorine, or —CH3.

### Claim 5 (depends on 3)

The compound according to claim 3, wherein, in formulas (1-1) to (1-12), X2, X3, Y2, and Y3 are fluorine.

### Claim 6 (depends on 3)

The compound according to claim 3, represented by any one of formula (1-1), formula (1-2), formula (1-5), formula (1-6), formula (1-11), or formula (1-12).

### Claim 7 (depends on 3)

The compound according to claim 3, represented by any one of formula (1-3), formula (1-4), formula (1-7), formula (1-8), formula (1-9), or formula (1-10).

### Claim 8 (depends on 3)

The compound according to claim 3, represented by any one of formula (1-1-A), formula (1-2-A), formula (1-5-A), formula (1-6-A), formula (1-11-A), and formula (1-12-A):
wherein, in formula (1-1-A), formula (1-2-A), formula (1-5-A), formula (1-6-A), formula (111-A), and formula (1-12-A), X1 and Y1 are independently hydrogen or fluorine.

### Claim 9 (depends on 8)

The compound according to claim 8, wherein, in formula (1-1-A), formula (1-2-A), formula (1-5-A), formula (1-6-A), formula (1-11-A), and formula (1-12-A), both of X1 and Y1 are hydrogen.

### Claim 10 (depends on 9)

The compound according to claim 9, represented by formula (1-1-A) and formula (1-2-A).

### Claim 11 (depends on 1)

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

### Claim 12 (depends on 11)

The liquid crystal composition according to claim 11, further containing at least one compound selected from the group consisting of compounds represented by formulas (2) to (4):
wherein, in formulas (2) to (4),
ring B1, ring B2, ring B3, and ring B4 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5diyl;
R11 and R12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10carbons, and in the alkyl and the alkenyl, at least one —CH2— may be replaced by —O—, and in the alkyl and the alkenyl, at least one hydrogen may be replaced by fluorine;
and
Z11, Z12, and Z13 are independently a single bond, —COO—, —CH2CH2—, —CH═CH—, or —C≡C—.

### Claim 13 (depends on 11)

The liquid crystal composition according to claim 11, further containing at least one compound selected from the group consisting of compounds represented by formulas (5) to (7):
wherein, in formulas (5) to (7),
ring C1, ring C2, and ring C3 are independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl;
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 —CH2— may be replaced by —O—, and in the alkyl and the alkenyl, at least one hydrogen may be replaced by fluorine;
X11 is fluorine, chlorine, —OCF3, —OCHF2, —CF3, —CHF2, —CH2F, —OCF2CHF2, or —OCF2CHFCF3;
Z14, Z15, and Z16 are independently a single bond, —COO—, —OCO—, —CH2O—, —OCH2—, —CF2O—, —OCF2—, —CH2CH2—, —CH═CH—, —C≡C—, or —(CH2)4—; and
L11 and L12 are independently hydrogen or fluorine.

### Claim 14 (depends on 11)

The liquid crystal composition according to claim 11, further containing at least one compound represented by formula (8):
wherein, in formula (8),
ring D1 is 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;
R14 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one —CH2— may be replaced by —O—, and in the alkyl and the alkenyl, at least one hydrogen may be replaced by fluorine;
X12 is —C≡N or —C≡C—C≡N;
Z17 is a single bond, —COO—, —OCO—, —CH2O—, —OCH2—, —CF2O—, —OCF2—, —CH2CH2—, or —C≡C—;
L13 and L14 are independently hydrogen or fluorine; and
i is 1, 2, 3, or 4.

### Claim 15 (depends on 11)

The liquid crystal composition according to claim 11, further containing at least one compound selected from the group consisting of compounds represented by formulas (9) to (15):
wherein, in formulas (9) to (15),
ring E1, ring E2, ring E3, and ring E4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl;
ring E5 and ring E6 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl;
R15 and R16 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 —CH2— may be replaced by —O—, and in the alkyl and the alkenyl, at least one hydrogen may be replaced by fluorine;
R17 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 —CH2—may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;
Z18, Z19, Z20, and Z21 are independently a single bond, —COO—, —OCO—, —CH2O—, —OCH2—, —CF2O—, —OCF2—, —CH2CH2—, —CF2OCH2CH2,or —OCF2CH2CH2—;
L15 and L16 are independently fluorine or chlorine;
S11 is hydrogen or methyl;
X is —CHF— or —CF2—; 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 1, 2, or 3.

### Claim 16 (depends on 11)

A liquid crystal display device, including the liquid crystal composition according to claim 11.