Liquid crystal compound having tercyclohexyl, liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-9994770-B2
Application number	US-201715453627-A
Country	US
Kind code	B2
Filing date	Mar 8, 2017
Priority date	Mar 10, 2016
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

Provided is a liquid crystal compound satisfying at least one of physical properties such as high stability to heat and light, a high clearing point (or high maximum temperature), low minimum temperature of a liquid crystal phase, small viscosity, suitable optical anisotropy, large dielectric anisotropy, a suitable elastic constant and 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), R 1 is alkoxy having 1 to 9 carbons or the like; R 2 is alkenyl having 2 to 10 carbons; Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH— or the like; and a and b are independently 0 or 1.

First claim

What is claimed is:

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

wherein, in formula (1),
R 1 is a group in which at least one —CH 2 — of alkyl having 1 to 10 carbons is replaced by —O—, and in the group, at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and at least one hydrogen may be replaced by fluorine;
R 2 is alkenyl having 2 to 10 carbons, and in the group, at least one hydrogen bonding with carbon forming a double bond may be replaced by fluorine or chlorine;
Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —OCH 2 —, —CH 2 O—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CF 2 CF 2 —, —CF═CF—, —(CH 2 ) 4 —, —CH═CH—(CH 2 ) 2 — or —(CH 2 ) 2 —CH═CH—; and
a and b are independently 0 or 1.

2. The compound according to claim 1 , wherein, in formula (1),
R 1 is alkoxy having 1 to 9 carbons, alkoxyalkyl having 1 to 9 carbons, alkenyloxy having 2 to 9 carbons or alkenyloxyalkyl having 2 to 9 carbons, and in the groups, at least one hydrogen may be replaced by fluorine;
R 2 is alkenyl having 2 to 10 carbons, and in the group, at least one hydrogen bonding with carbon forming a double bond may be replaced by fluorine;
Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —OCH 2 — or —CH 2 O—; and
a and b are independently 0 or 1.

3. 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),
R 1 is alkoxy having 1 to 9 carbons or alkenyloxy having 2 to 9 carbons, and in the groups, at least one hydrogen may be replaced by fluorine;
R 2 is alkenyl having 2 to 10 carbons, and in the group, at least one hydrogen bonding with carbon forming a double bond may be replaced by fluorine; and
Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —OCH 2 — or —CH 2 O—.

4. The compound according to claim 1 , represented by any one of formulas (1-5) to (1-10):

wherein, in formulas (1-15) to (1-22), R 3 is alkyl having 1 to 9 carbons.

5. The compound according to claim 1 , represented by any one of formulas (1-11) to (1-14):

wherein, in formulas (1-11) to (1-14),
R 1 is alkoxy having 1 to 9 carbons; and
R 2 is alkenyl having 2 to 10 carbons, and in the group, at least one hydrogen bonding with carbon forming a double bond may be replaced by fluorine.

6. The compound according to claim 1 , represented by any one of formulas (1-15) to (1-22):

Z 11 , Z 12 and Z 13 are independently a single bond, —COO—, —CH 2 CH 2 —, —CH═CH— or —C≡C—; and
in formula (3), when all of ring B 1 , ring B 2 and ring B 3 are 1,4-cyclohexylene, R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the monovalent groups, at least one hydrogen may be replaced by fluorine; and
in formula (4), when all of ring B 1 , ring B 2 , ring B 3 and ring B 4 are 1,4-cyclohexylene, R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the monovalent groups, at least one hydrogen may be replaced by fluorine.

7. The compound according to claim 1 , represented by any one of formulas (1-23) to (1-26):

wherein, in formulas (1-23) to (1-26), R 3 is alkyl having 1 to 6 carbons.

8. A liquid crystal composition, containing at least one compound 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 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the groups, at least one —CH 2 — may be replaced by —O—, and in the monovalent groups, at least one hydrogen may be replaced by fluorine;
ring B 1 , ring B 2 , ring B 3 and ring B 4 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

wherein, in formulas (1-5) to (1-10),
R 1 is alkoxy having 1 to 9 carbons or alkenyloxy having 2 to 9 carbons; and
R 2 is alkenyl having 2 to 10 carbons, and in the group, at least one hydrogen bonding with carbon forming a double bond may be replaced by fluorine.

10. The liquid crystal composition according to claim 8 , further containing at least one compound selected from the group of compounds represented by formulas (5) to (7):

wherein, in formulas (5) to (7),
R 13 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the groups, at least one —CH 2 — may be replaced by —O—, and in the monovalent groups, at least one hydrogen may be replaced by fluorine;
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 C 1 , ring C 2 and ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene, 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;
Z 14 , Z 15 and Z 16 are independently a single bond, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CH═CH—, —C≡C— or —(CH 2 ) 4 —; and
L 11 and L 12 are independently hydrogen or fluorine.

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

wherein, in formula (8),
R 14 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the groups, at least one —CH 2 — may be replaced by —O—, and in the monovalent groups, at least one hydrogen may be replaced by fluorine;
X 12 is —C≡N or —C≡C—C≡N;
ring D 1 is 1,4-cyclohexylene, 1,4-phenylene, 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;
Z 17 is a single bond, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 — or —C≡C—;
L 13 and L 14 are independently hydrogen or fluorine; and
i is 1, 2, 3 or 4.

12. The liquid crystal composition according to claim 8 , further containing at least one compound selected from the group of compounds represented by formulas (9) to (15):

wherein, in formulas (9) to (15),
R 15 and R 16 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the groups, at least one —CH 2 — may be replaced by —O—, and in the monovalent groups, at least one hydrogen may be replaced by fluorine;
R 17 is hydrogen, fluorine, alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the a

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Tanaka Hiroyuki
• TAKATA Akihiro

Classifications

• C09K19/3003 Primary

  Compounds containing at least two rings in which the different rings are directly linked (covalent bond) · CPC title

• C09K19/3001

  Cyclohexane rings · CPC title

• C09K2019/3004

  Cy-Cy · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C09K2019/3016

  Cy-Ph-Ph · CPC title