Liquid crystal compound having 1,1,3,3-tetrafluoroallyloxy group, liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-9951277-B2
Application number	US-201515121383-A
Country	US
Kind code	B2
Filing date	Feb 19, 2015
Priority date	Feb 25, 2014
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

To show a liquid crystal compound satisfying at least one of physical properties such as a high stability to heat, light or the like, a high clearing point, a low minimum temperature of a liquid crystal phase, a small viscosity, a suitable optical anisotropy, a large dielectric anisotropy, a suitable elastic constant and an excellent compatibility with other liquid crystal compounds, a liquid crystal composition containing the compound and a liquid crystal display device including the composition.
A compound represented by formula (1):

wherein, in formula (1),
for example, R 1 is alkyl having 1 to 15 carbons; ring A 1 and ring A 2 are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one piece of hydrogen is replaced by halogen, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl; Z 1 and Z 2 are a single bond or —CF 2 O—; L 1 , L 2 and L 3 are halogen or hydrogen; and a is 0 to 3.

First claim

What is claimed is:

1. A compound, represented by formula (1):

wherein, in formula (1),
R 1 is alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —CH 2 — may be replaced by —O—, and at least one piece of —CH 2 CH 2 — may be replaced by —CH═CH—, and in the groups, at least one piece of hydrogen may be replaced by halogen;
ring A 1 and ring A 2 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, 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 or pyridine-2,5-diyl;
Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —C≡C—, —CH═CH—, —CF═CF—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—;
L 1 , L 2 and L 3 are independently hydrogen or halogen; and
a is 0, 1, 2 or 3.

2. The compound according to claim 1 , wherein, in formula (1), R 1 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.

3. The compound according to claim 1 , wherein, in formula (1), Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —C≡C—, —CH═CH—, —CF 2 O— or —COO—.

4. The compound according to claim 1 , represented by any one of formulas (1-1) to (1-4):

wherein, in formulas (1-1) to (1-4),
ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one piece of hydrogen is replaced by halogen, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl;
Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —CF 2 O— or —COO—;
R 1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons; and
L 1 and L 2 are independently hydrogen or halogen.

5. The compound according to claim 4 ,
wherein, in formulas (1-1) to (1-4),
ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one piece of hydrogen is replaced by fluorine or chlorine, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl;
Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond, —CH 2 CH 2 —, —CH═CH— or —CF 2 O—;

R 1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons; and
L 1 and L 2 are independently hydrogen or fluorine

6. The compound according to claim 1 , represented by any one of formulas (1-5) to (1-12):

wherein, in formulas (1-5) to (1-12),
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl;
Z 1 and Z 2 are independently a single bond or —CF 2 O—;
R 1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons; and
L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 are independently hydrogen or fluorine.

7. The compound according to claim 1 , represented by any one of formulas (1-13) to (1-23):

wherein, in formulas (1-13) to (1-23),
R 1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons; and
L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 are independently hydrogen or fluorine.

8. A liquid crystal composition, containing at least one of the compounds according to claim 1 .

9. The liquid crystal composition according to claim 8 , further containing at least one compound selected from the group of compounds represented by formulas (2) to (4):

wherein, in formulas (2) to (4),
R 11 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 —CH 2 — may be replaced by —O—;
X 11 is fluorine, chlorine, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 or —OCF 2 CHFCF 3 ;
ring B 1 , ring B 2 and ring B 3 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;
Z 11 , Z 12 and Z 13 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —CF 2 O—, —OCF 2 —, —CH 2 O— or —(CH 2 ) 4 —; and
L 11 and L 12 are independently hydrogen or fluorine.

10. The liquid crystal composition according to claim 8 , further containing at least one compound selected from the group of compounds represented by formula (5):

wherein, in formula (5),
R 12 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 —CH 2 — may be replaced by —O—;
X 12 is —C≡N or —C≡C—C≡N;
ring C 1 is 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;
Z 14 is a single bond, —CH 2 CH 2 —, —C≡C—, —COO—, —CF 2 O—, —OCF 2 — or —CH 2 O—;
L 13 and L 14 are independently hydrogen or fluorine; and
i is 1, 2, 3 or 4.

11. The liquid crystal composition according to claim 8 , further containing at least one compound selected from the group of compounds represented by formulas (6) to (12):

wherein, in formulas (6) to (12),
R 13 and R 14 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 —CH 2 — may be replaced by —O—, and at least one piece of hydrogen may be replaced by fluorine;
R 15 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 —CH 2 — may be replaced by —O—, and at least one piece of hydrogen may be replaced by fluorine;
S 11 is hydrogen or methyl;
X is —CF 2 —, —O— or —CHF—;
ring D 1 , ring D 2 , ring D 3 and ring D 4 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 D 5 and ring D 6 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl;
Z 15 , Z 16 , Z 17 and Z 18 are independently a single bond, —CH 2 CH 2 —, —COO—, —CH 2 O—, —OCF 2 — or —OCF 2 CH 2 CH 2 —;
L 15 and L 16 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 1, 2 or 3.

12. The liquid crystal composition according to claim 8 , further containing at least one compound selected from the group of compounds represented by formulas (13) to (15):

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• TAKATA Akihiro
• Kubo Takahiro

Classifications

• C07C43/225

  containing halogen · CPC title

• C09K2019/3077

  Cy-Cy-COO-Ph · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C07D309/06

  Radicals substituted by oxygen atoms · CPC title

• C07D213/30

  Oxygen atoms · CPC title