# US 2013/0240784 A1 · Compound having dihydrophenanthrene, liquid crystal composition and liquid crystal display device

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- Number: US 2013/0240784 A1
- Document ID: US20130240784A1
- Status: Published application
- Kind: A1
- Application number: 13/991,170
- Filed: 2011-12-09
- Published: 2013-09-19
- Earliest claimed: 2010-12-21
- Assignees: Jnc Petrochemical Corporation; Jnc Corporation
- Inventors: Kenji Hirata; Hiroki Ookawa
- Web page: https://patentgrep.com/patent/US20130240784A1

## CPC

- C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C07C 25/22: with condensed rings
- C07C 25/24: Halogenated aromatic hydrocarbons with unsaturated side chains
- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- C07C 2603/26: Phenanthrenes; Hydrogenated phenanthrenes
- C09K 2019/3425: {Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems}
- G02F 1/13712: {the liquid crystal having negative dielectric anisotropy}
- G02F 2201/086: UV absorbing
- 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

To provide a liquid crystal compound having a large negative dielectric anisotropy (Δ∈), and having at least one of characteristics such as a high stability to heat, light and so forth, a high clearing point, a suitable refractive index anisotropy (Δn) and an excellent compatibility with other liquid crystal compounds, and an intermediate thereof. A solution is a compound represented by formula (1): wherein, for example, R1 and R2 are alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons; ring A1, ring A2 and ring A3 are 1,4-cyclohexylene or 1,4-phenylene; Z1, Z2 and Z3 are a single bond or —(CH2)2—; X is —CF2— or —CHF—; and l, m and n are 0 or 1.

## Claims

### Claim 1

A compound represented by formula (1):
wherein, in formula (1), R1 and R2 are independently hydrogen, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons, and in the alkyl, the alkenyl, the alkoxy, the alkoxyalkyl and the alkenyloxy, at least one of hydrogen may be replaced by fluorine;
ring A1, ring A2 and ring A3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl, and in the rings, at least one of hydrogen may be replaced by fluorine;
Z1, Z2 and Z3 are independently a single bond, —(CH2)2—, —OCH2—, —CH2O—, —COO—, —COO—, —CF2O— or —OCF2—;
X is independently —C(═O)—, —CHF— or —CF2—; and
l, m and n are independently 0 or 1.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein, in formula (1), R1 and R2 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons; and
ring A1, ring A2 and ring A3 are independently 1,4-cyclohexylene,
1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene.

### Claim 3 (depends on 2)

The compound according to claim 2, wherein, in formula (1), ring A1, ring A2 and ring A3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein, in formula (1), a sum of l, m and n is 0, 1 or 2.

### Claim 5 (depends on 1)

The compound according to claim 1, represented by formula (1-1):
wherein, in formula (I-1), ring A1 is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene;
R1 and R2 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons;
Z1 is a single bond, —(CH2)2—, —OCH2—, —CH2O—, —COO—, —COO—, —CF2O— or —OCF2—;
X is independently —C(═O)—, —CHF— or —CF2—; and 1 is 0 or 1.

### Claim 6 (depends on 5)

The compound according to claim 5, wherein, in formula (1), Z1 is a single bond, —(CH2)2—, —CH2O—, —COO— or —CF2O—.

### Claim 7 (depends on 6)

The compound according to claim 6, wherein, in formula (1-1), ring A1 is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene or 2,3-difluoro-1,4-phenylene.

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 8)

The liquid crystal composition according to claim 8, further containing at least one compound selected from the group of compounds represented by formulas (2), (3), (4), (5), (6) and (7):
wherein, in the formulas, R3 and R4 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 hydrogen may be replaced by fluorine, and at least one of —CH2— may be replaced by —O—;
ring C1, ring C2, ring C3 and ring C4 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 decahydro-2,6-naphthalene;
Z4, Z5, Z6 and Z7 are independently —(CH2)2—, —COO—, —CH2O—, —OCF2—, —OCF2(CH2)2— or a single bond;
L5 and L6 are independently fluorine or chlorine; and
p, q, r, s, t and u are independently 0 or 1, and a sum of q, r, s and t is 1 or 2.

### Claim 10 (depends on 8)

The liquid crystal composition according to claim 8, further containing at least one compound selected from the group of compounds represented by formulas (8), (9) and (10):
wherein, in the formulas, R5 and R6 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 hydrogen may be replaced by fluorine, and at least one of —CH9— may be replaced by —O—;
ring D1, ring D2 and ring D3 are independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; and
Z8 and Z9 are independently —C═C—, —COO—, —(CH2)2—, —CH—CH— or a single bond.

### 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 (8), (9) and (10).

### Claim 12 (depends on 8)

The liquid crystal composition according to claim 8, further containing at least one optically active compound and/or one polymerizable compound.

### Claim 13 (depends on 8)

The liquid crystal composition according to claim 8, containing at least one antioxidant and/or one ultraviolet light absorber.

### Claim 14 (depends on 8)

A liquid crystal display device including the liquid crystal composition according to claim 8.