Liquid crystal compound having polyfluoro-2-butenoxy group, liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-10358602-B2
Application number	US-201715649803-A
Country	US
Kind code	B2
Filing date	Jul 14, 2017
Priority date	Jul 28, 2016
Publication date	Jul 23, 2019
Grant date	Jul 23, 2019

Abstract

Provided are a liquid crystal compound having larger dielectric anisotropy and superb heating reliability in comparison with a similar compound, a liquid crystal composition containing the compound and a liquid crystal display device including the composition. A compound is represented by formula (1).

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

First claim

What is claimed is:

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

wherein, in formula (1),
R 1 is alkyl having 1 to 15 carbons, and in the R 1 , at least one —CH 2 — may be replaced by —O— or —S—, at least one —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and at least one hydrogen may be replaced by halogen;
ring A 1 is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one 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, and at least one hydrogen directly bonded to the rings may be replaced by halogen;
Z 1 is 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 and L 2 are independently hydrogen or halogen;
Y 1 and Y 2 are independently hydrogen or halogen; and
a is 1, 2, 3 or 4.

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 is 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 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;
L 1 and L 2 are independently hydrogen, fluorine or chlorine; and
Y 1 and Y 2 are independently hydrogen, fluorine or chlorine.

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 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;
L 1 and L 2 are independently hydrogen or fluorine; and
Y 1 and Y 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;
L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 are independently hydrogen or fluorine; and
Y 1 and Y 2 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;
L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 are independently hydrogen or fluorine; and
Y 1 and Y 2 are independently hydrogen or fluorine.

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 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
Z 11 , Z 12 and Z 13 are independently a single bond, —COO—, —CH 2 CH 2 —, —CH═CH— or —C≡C—.

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 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 1 and L 12 are independently hydrogen or fluorine.

11. The liquid crystal composition according to claim 8 , further containing a compound represented by formulas (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 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 , R 16 and R 17 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 at least one hydrogen may be replaced by fluorine, and R 17 may be hydrogen or fluorine;
ring E 1 , ring E 2 , ring E 3 and ring E 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl;
ring E 5 and ring E 6 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl;
Z

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• TAKATA Akihiro

Classifications

• C09K19/44 Primary

  containing compounds with benzene rings directly linked · CPC title

• C09K19/066

  containing one heterocyclic ring having oxygen as heteroatom · CPC title

• C09K2019/0466

  the linking chain being a -CF2O- chain · CPC title

• C09K19/04 Primary

  characterised by the chemical structure of the liquid crystal components {, e.g. by a specific unit} · CPC title

• C09K2019/0444

  characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group · CPC title