# US 8,465,674 B2 · Decahydronaphthalene compound, liquid crystal composition including the compound and liquid crystal display device containing the liquid crystal composition

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- Number: US 8,465,674 B2
- Document ID: US8465674B2
- Status: Granted
- Kind: B2
- Application number: 13/390,936
- Filed: 2010-08-09
- Published: 2012-06-14
- Granted: 2013-06-18
- Earliest claimed: 2009-08-18
- Assignees: Jnc Corporation; Jnc Petrochemical Corporation
- Applicants: Tokifumi Masukawa
- Inventors: Tokifumi Masukawa
- Web page: https://patentgrep.com/patent/US8465674B2

## CPC

- C09K 19/322: {Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring}
- C09K 2019/0407: {containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone}
- C09K 2019/326: {containing a decahydronaphthalene, e.g. -2,6-diyl (decalin)}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A compound represented by the formula (1) is provided. In the formula (1), for example, R1 and R2 are alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyl having 2 to 10 carbons; the ring A and the ring B are 1,4-cyclohexylene or 1,4-phenylene; Z1 and Z2 are a single bond and Z3 is —CH2O— or —OCH2—; Y1 and Y2 are halogen, —CF3, —CHF2, —CH2F, —OCF3, —OCHF2 or —OCH2F; and m and n is 0, 1 or 2, p is 1 or 2, and the sum of m, n and p is 1, 2 or 3.

## Claims

### Claim 1

A compound represented by the formula (1):
in the formula (1), R1 and R2 are independently alkyl having 1 to 10 carbons, and in the alkyl, arbitrary —CH2— may be replaced by —O—, —S—, —CO— or —SiH2 —, and arbitrary —(CH2)2— may be replaced by —CH═CH— or —C≡C—;
the ring A and the ring B are independently 1,4-cyclohexylene or 1,4-phenylene, and in the rings, arbitrary one —CH2— may be replaced by —O—, —S—, —CO— or —SiH2— and arbitrary —(CH2)2— may be replaced by —CH═CH—, in the 1,4-phenylene, arbitrary —CH═ may be replaced by —N═, and in the rings, arbitrary hydrogen may be replaced by halogen, —CF3, —CHF2, —CH2F, —OCF3, —OCHF2 or —OCH2 F;
Z1 and Z2 are independently a single bond or alkylene having 1 to 4 carbons, and in the alkylene, arbitrary —CH2— may be replaced by —O—, —S—, —CO— or —SiH2—, arbitrary —CH2)2— may be replaced by —CH═CH— or —C≡C—, and arbitrary hydrogen may be replaced by halogen; and Z3 is —CH2O— or —OCH2—;
Y1 and Y2 are independently halogen, —CF3, —CHF2, —CH2F, —OCF3, —OCHF2 or —OCH2F; and
m and n are independently 0, 1 or 2, p is 1 or 2, and the sum of m, n and p is 1, 2 or 3.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein in the formula (1), Rl and R2 are independently alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyl having 2 to 10 carbons;
the ring A and the ring B are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene or pyrimidine-2,5-diyl;
Z1 and Z2 are independently a single bond, —(CH2)2—, —(CH2)4—, —COO—, —OCO—, —CF2O—, —OCF2—CH═CH—, —CF═CF—, —CH≡C—, —CH2O— or —OCH2—; and
Y1 and Y2 are independently fluorine or chlorine.

### Claim 3 (depends on 2)

The compound according to claim 2, wherein in the formula (1), R2 is alkoxy having 1 to 9 carbons.

### Claim 4 (depends on 2)

The compound according to claim 2, wherein in the formula (1), Z3 is —CH2O—.

### Claim 5 (depends on 2)

The compound according to claim 2, wherein in the formula (1), Rl is alkyl having 1 to 7 carbons, alkoxy having 2 to 6 carbons or alkenyl having 2 to 7 carbons; and R2 is alkoxy having 2 to 6 carbons;
the ring A and the ring B are independently 1,4-cyclohexylene or 1,4-phenylene;
Z1 and Z2 are independently a single bond, —(CH2)2—, —COO—, —OCO—, —CH═CH—, —CH2O— or —OCH2—; and
Y1 and Y2 are fluorine.

### Claim 6 (depends on 2)

The compound according to claim 2, wherein in the formula (1), Z1 and Z2 are a single bond.

### Claim 7

A compound represented by the formula (1-1):
in the formula (1-1), R1 is alkyl having 1 to 7 carbons, alkoxy having 2 to 6 carbons or alkenyl having 2 to 7 carbons; and R2 is alkoxy having 2 to 6 carbons.

### Claim 8

A compound represented by the formula (1-2) or (1-3):
in the formulas (1-2) and (1-3), R1 is alkyl having 1 to 7 carbons, alkoxy having 2 to 6 carbons or alkenyl having 2 to 7 carbons; R2 is alkoxy having 2 to 6 carbons; and the ring A and the ring B are independently 1,4-cyclohexylene or 1,4-phenylene.

### Claim 9

A compound represented by the formula (1-4):
in the formula (1-4), R1 is alkyl having 1 to 7 carbons, alkoxy having 2 to 6 carbons or alkenyl having 2 to 7 carbons; and R2 is alkoxy having 2 to 6 carbons.

### Claim 10

A compound represented by the formula (1-5) or (1-6):
in the formulas (1-5) and (1-6), RI is alkyl having 1 to 7 carbons, alkoxy having 2 to 6 carbons or alkenyl having 2 to 7 carbons; R2 is alkoxy having 2 to 6 carbons; and the ring A and the ring B are independently 1,4-cyclohexylene or 1,4-phenylene.

### Claim 11 (depends on 2)

A liquid crystal composition including a first component and a second component, wherein the first component is at least one selected from compounds according to claim 2.

### Claim 12 (depends on 11)

The liquid crystal composition according to claim 11, including at least one compound selected from the group of compounds represented by the general formulas (2), (3) and (4) as the second component:
in the formulas (2)-(4), R3 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, arbitrary hydrogen may be replaced by fluorine and arbitrary —CH2— may be replaced by —O—;
Xl is independently fluorine, chlorine, —OCF3, —OCHF2, —CF3 , —CHF2, —CH2F, —OCF2 CHF2 or —OCF2 CHFCF3;
the ring Al , the ring A2 and the ring A3 are independently 1,4-cyclohexylene, 1,3-dioxane-2,5diyl-pyrimidine-2,5-diyl, 1-tetrahydropyran-2,5-diyl or 1,4-phenylene in which arbitrary hydrogen may be replaced by fluorine;
Z4 and Z5 are independently —(CH2)2—, —CH2)4 —, —COO—, —CF2O—, —OCF2—, —CH═CH—, —C≡C—, —CH2O— or a single bond; and
L1 and L2 are independently hydrogen or fluorine.

### Claim 13 (depends on 11)

The liquid crystal composition according to claim 11, including at least one compound selected from the group of compounds represented by the general formula (5) as the second component:
in the formula (5), R4 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, arbitrary hydrogen may be replaced by fluorine and arbitrary —CH2— may be replaced by —O—;
X2 is —C≡N or —C≡C—CN;
the ring B1 , the ring B2 and the ring B3 are independently 1,4-cyclohexylene, 1,4-phenylene in which arbitrary hydrogen may be replaced by fluorine, 1,3-dioxane-2,5-diyl, 1-tetrahydropyran-2,5-diyl or pyrimidine-2,5-diyl;
Z6 is —(CH2)2—, —COO—, —CF2O—, —OCF2—, —C≡C—, —CH2O— or a single bond;
L3 and L4 are independently hydrogen or fluorine; and
q is 0, 1 or 2, and r is 0 or 1.

### Claim 14 (depends on 11)

The liquid crystal composition according to claim 11, including at least one compound selected from the group of compounds represented by the general formulas (6), (7), (8), (9), (10) and (11) as the second component:
in the formulas (6)-(11), 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 arbitrary —CH2— may be replaced by —O—, and in the alkenyl arbitrary hydrogen may be replaced by fluorine;
the ring C1, the ring C2 , the ring C3 and the ring C4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which arbitrary hydrogen may be replaced by fluorine, 6-tetrahydropyran-2,5-diyl or decahydro-2,6-naphthalene;
Z7 , Z8 , Z9 and Z10 are independently —(CH2)2—, —COO—, —CH2O—, —OCF2—, —OCF2(CH2)2— or a single bond;
L5 and L6 are independently fluorine or chlorine; and
j, k, 1, m, n and s are independently 0 or 1, and the sum of k, 1, m and n is 1 or 2.

### Claim 15 (depends on 11)

The liquid crystal composition according to claim 11, including at least one compound selected from the group of compounds represented by the general formulas (12), (13) and (14) as the second component:
in the formulas (12)-(14), R7 and R8 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkenyl, arbitrary hydrogen may be replaced by fluorine and arbitrary —CH2— may be replaced by —O—;
the ring D1 , the ring D2 and the 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
11 and Z12 are independently —C≡C—, —COO—, —(CH2)2—, —CH═CH— or a single bond.

### Claim 16 (depends on 12)

The liquid crystal composition according to claim 12, further including at least one compound selected from the group of compounds represented by the general formula (5):
in the formula (5), R4 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, arbitrary hydrogen may be replaced by fluorine and arbitrary —CH2— may be replaced by —O—;
X2 is —C≡N or —C═C—CN;
the ring B1, the ring B2 and the ring B3 are independently 1,4-cyclohexylene, 1,4-phenylene in which arbitrary hydrogen may be replaced by fluorine, 1,3-dioxane-2,5-diyl, 1-tetrahydropyran-2,5-diyl or pyrimidine-2,5-diyl;
Z6 is —(CH2)2—, —COO—, —CF2O—, —OCF2—, —C≡C—, —CH2— or a single bond;
L3 and L4 are independently hydrogen or fluorine; and
q is 0, 1 or 2, and r is 0 or 1.

### Claim 17 (depends on 12)

The liquid crystal composition according to claim 12, further including at least one compound selected from the group of compounds represented by the general formulas (12), (13) and (14):
in the formulas (12)-(14), R7 and R8 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkenyl, arbitrary hydrogen may be replaced by fluorine and arbitrary —CH2— may be replaced by —O—;
the ring D1, the ring D2 and the 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
Z11 and Z12 are independently —C≡C—, —COO—, —(CH2) 2—, —CH— or a single bond.

### Claim 18 (depends on 13)

The liquid crystal composition according to claim 13, further including at least one compound selected from the group of compounds represented by the general formulas (12), (13) and (14):
in the formulas (12)-(14), R7 and R8 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkenyl, arbitrary hydrogen may be replaced by fluorine and arbitrary —CH2— may be replaced by —O—;
the ring D1, the ring D2 and the 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
Z11 and Z12 are independently —C≡C—, —COO—, —(CH2)2—, —CH═CH— or a single bond.

### Claim 19 (depends on 14)

The liquid crystal composition according to claim 14, further including at least one compound selected from the group of compounds represented by the general formulas (12), (13) and (14):
in the formulas (12)-(14), R7 and R8 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkenyl, arbitrary hydrogen may be replaced by fluorine and arbitrary —CH2— may be replaced by —O—;
the ring D1, the ring D2 and the 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
Z11 and Z12 are independently —C≡C—, —COO—, —(CH2)2—, —CH═CH— or a single bond.

### Claim 20 (depends on 11)

The liquid crystal composition according to claim 11, further including at least one optically active compound and/or at least one polymerizable compound.

### Claim 21 (depends on 11)

The liquid crystal composition according to claim 11, further including at least one antioxidant and/or at least one ultraviolet light absorber.

### Claim 22 (depends on 11)

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