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

Patent metadata

Field	Value
Publication number	US-10563126-B2
Application number	US-201615579193-A
Country	US
Kind code	B2
Filing date	May 10, 2016
Priority date	Jun 8, 2015
Publication date	Feb 18, 2020
Grant date	Feb 18, 2020

Abstract

A liquid crystal compound is represented by formula (1):

In formula (1), R 1 is alkyl or the like; ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-phenylene or the like; Z 1 , Z 2 and Z 3 are independently a single bond, —CF 2 O— or the like; X 1 is fluorine, chlorine, —CF 3 or the like; L 1 and L 2 are independently hydrogen, fluorine or the like; a and b are independently 0, 1, 2 or 3; and W is a group represented by formula (1a) or formula (1b);

In formula (1a) and formula (1b), L 3 to L 8 are independently hydrogen, fluorine or the like.

First claim

What is claimed is:

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

wherein, in formula (1),
R 1 is hydrogen, fluorine or alkyl having 1 to 20 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine;
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl or pyridine-2,5-diyl, and at least one hydrogen on the rings may be replaced by halogen;
Z 1 , Z 2 and Z 3 are independently a single bond or alkylene having 1 to 4 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O— or —COO—, and at least one —(CH 2 ) 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen;
X 1 is fluorine, chlorine, —SF 5 , —C≡N, —N═C═S, —C≡C—CF 3 , —C≡C—CN, polyfluoroalkyl having 1 to 7 carbons, perfluoroalkyl having 1 to 7 carbons, polyfluoroalkenyl having 1 to 7 carbons, perfluoroalkoxy having 1 to 7 carbons, polyfluoroalkoxy having 1 to 7 carbons or perfluoroalkoxy having 1 to 7 carbons;
L 1 and L 2 are independently hydrogen, fluorine or chlorine;
a and b are independently 0, 1, 2 or 3, and a sum of a and b is 3 or less, and when a or b is two or more, two of rings A 1 and A 2 and two of Z 1 and Z 2 may be identical or different; and
W is a group represented by formula (1a) or formula (1b);

wherein, in formula (1a) and formula (1b),
L 3 , L 4 , L 5 , L 6 , L 7 and L 8 are independently hydrogen, fluorine, or chlorine.

2. The compound according to claim 1 , wherein,
in formula (1),
R 1 is hydrogen, fluorine or alkyl having 1 to 20 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine;
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which one at least hydrogen may be replaced by halogen, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl;
Z 1 , Z 2 and Z 3 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —(CH 2 ) 4 —, —(CH 2 ) 2 CF 2 O—, —(CH 2 ) 2 OCF 2 —, —CF 2 O(CH 2 ) 2 —, —OCF 2 (CH 2 ) 2 —, —CH═CH—(CH 2 ) 2 — or —(CH 2 ) 2 —CH═CH—;
X 1 is fluorine, chlorine, —SF 5 , —C≡N, —N═C═S, —C≡C—CF 3 , —C≡C—C≡N, polyfluoroalkyl having 1 to 3 carbons, perfluoroalkyl having 1 to 3 carbons, polyfluoroalkenyl having 1 to 3 carbons, perfluoroalkenyl having 1 to 3 carbons, polyfluoroalkoxy having 1 to 3 carbons or perfluoroalkoxy having 1 to 3 carbons; and
L 1 and L 2 are independently hydrogen or fluorine.

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

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

wherein, in formulas (1-1) to (1-12), R 1 is hydrogen, fluorine or alkyl having 1 to 10 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine;
ring A 1 , ring A 2 and ring A 3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one hydrogen may be replaced by halogen, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl;
Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —(CH 2 ) 4 —, —(CH 2 ) 2 CF 2 O—, —(CH 2 ) 2 OCF 2 —, —CF 2 O(CH 2 ) 2 —, —OCF 2 (CH 2 ) 2 —, —CH═CH—(CH 2 ) 2 — or —(CH 2 ) 2 —CH═CH—;
X 1 is fluorine, —CF 3 or —OCF 3 ;
L 1 and L 2 are independently hydrogen or fluorine; and
L 3 , L 4 , L 5 , L 6 , L 7 and L 8 are independently hydrogen or fluorine.

5. The compound according to claim 4 , wherein, in formulas (1-1) to (1-12), R 1 is alkyl having 1 to 10 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine; and
Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —C≡C—, —(CH 2 ) 2 OCF 2 — or —OCH 2 —.

6. The compound according to claim 5 , represented by any one of formulas (1-3), (1-5), (1-6), (1-9), (1-11) and (1-12):

wherein R 1 is alkyl having 1 to 10 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine;
ring A 2 and ring A 3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one hydrogen may be replaced by halogen, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl;
Z 2 , Z 3 and Z 4 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —C≡C—, —(CH 2 ) 2 OCF 2 — or —OCH 2 —;
X 1 is fluorine, —CF 3 or —OCF 3 ;
L 1 and L 2 are independently hydrogen or fluorine; and
L 3 , L 4 , L 5 , L 6 , L 7 and L 8 are independently hydrogen or fluorine.

7. The compound according to claim 5 , represented by any one of formulas (1-3), (1-5) and (1-6), and R 1 being alkoxy having 1 to 6 carbons:

wherein R 1 is alkyl having 1 to 10 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine;
ring A 2 and ring A 3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one hydrogen may be replaced by halogen, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl;
Z 2 , Z 3 and Z 4 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —C≡C—, —(CH 2 ) 2 OCF 2 — or —OCH 2 —;
X 1 is fluorine, —CF 3 or —OCF 3 ;
L 1 and L 2 are independently hydrogen, fluorine or chlorine; and
L 3 , L 4 and L 5 are independently hydrogen or fluorine.

8. A liquid crystal composition, containing the 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, in the alkyl or the alkenyl, at least one —CH 2 — may be replaced by —O—, and 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

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Yano Tomohiro

Classifications

• C09K19/32

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title

• C09K19/52

  characterised by components which are not liquid crystals, e.g. additives {with special physical aspect: solvents, solid particles} · CPC title

• C09K2019/3004

  Cy-Cy · CPC title

• C09K2019/3027

  Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title