Liquid crystal compound having benzopyran skeleton, liquid crystal composition, and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-10428273-B2
Application number	US-201715655918-A
Country	US
Kind code	B2
Filing date	Jul 21, 2017
Priority date	Jul 22, 2016
Publication date	Oct 1, 2019
Grant date	Oct 1, 2019

Abstract

Shown are 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 negative dielectric anisotropy, a suitable elastic constant and satisfactory compatibility with other liquid crystal compounds, a liquid crystal composition containing the compound and a liquid crystal display device including the composition. A compound is represented by formula (1), a liquid crystal composition contains the compound, or the like

First claim

What is claimed is:

1. A liquid crystal composition, containing at least one compound represented by formula (1) as component (a):

wherein, in formula (1),
R 1 and R 2 are independently hydrogen, alkyl having 1 to 16 carbons, alkenyl having 2 to 16 carbons, cyclopropyl, cyclobutyl or cyclopentyl, and in the alkyl and the alkenyl, at least one —CH 2 —is optionally replaced by —O—, —S—, —CO—, —COO—, —OCO—, —OCOO—, —C≡C—, cyclopropane-1,2-diyl or —Si(CH 3 ) 2 —, and in the groups, at least one hydrogen is optionally replaced by fluorine or chlorine, and in the groups, at least one —CH 3 is optionally replaced by any one of monovalent groups (G1) to (G4) below;

wherein, in groups (G1) to (G4),
R 3 is alkyl having 1 to 12 carbons or alkenyl having 2 to 12 carbons, and in the alkyl and the alkenyl, at least one —CH 2 — is optionally replaced by —O—, and in the groups, at least one hydrogen is optionally replaced by fluorine or chlorine; and

in formula (1),
ring A 1 and ring A 2 are independently 1 ,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, decahydronaphthalene-2,6-diyl, tetrahydronaphthalene-2,6-diyl or naphthalene-2,6-diyl, and in the groups, one or two pieces of —CH 2 — is optionally replaced by —O—, —S—, —CO—, —CF 2 —, —SiH 2 — or —Si(CH 3 ) 2 —, and one or two pieces of —CH 2 CH 2 — is optionally replaced by —CH═CH— or —CH═N—, and in the groups, at least one hydrogen on an aromatic ring is optionally replaced by halogen, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 , —OCH 2 F, or —C≡N;
Z 1 and Z 2 are independently a single bond or alkylene having 1 to 4 carbons, and one —CH 2 — is optionally replaced by —O— or —CO—, and at least one —CH 2 CH 2 — is optionally replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen is optionally replaced by fluorine or chlorine;
X, L 1 and L 2 are independently hydrogen or halogen;
Y is —CO— or —CF 2 —; and
a and b are independently 0, 1 or 2.

2. The liquid crystal composition according to claim 1 , further containing at least one compound selected from the group of compounds represented by formulas (2) to (4) as component (b):

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 alkyl and the alkenyl, at least one —CH 2 —is optionally replaced by —O—, and in the groups, at least one hydrogen is optionally 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—.

3. The liquid crystal composition according to claim 1 , wherein component (a) is at least one compound represented by formula (1-1):

wherein, in formula (1-1),
R 1 and R 2 are independently hydrogen, alkyl having 1 to 14 carbons or alkenyl having 2 to 14 carbons, and in the alkyl and the alkenyl, one or two pieces of —CH 2 — is optionally replaced by —O—, and in the groups, at least one hydrogen is optionally replaced by fluorine, and in the groups, at least one —CH 3 is optionally replaced by any one of monovalent groups (G1) to (G4) below;

wherein, in groups (G1) to (G4),
R 3 is alkyl having 1 to 10 carbons, and in the alkyl, at least one —CH 2 — is optionally replaced by —O—; and

in formula (1-1),
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, decahydronaphthalene-2,6-diyl, tetrahydronaphthalene-2,6-diyl or naphthalene-2,6-diyl, and in the groups, one or two pieces of —CH 2 — is optionally replaced by —O—, and one or two pieces of —CH 2 CH 2 — is optionally replaced by —CH═CH—, and in the groups, at least one hydrogen on an aromatic ring is optionally replaced by fluorine;
Z 1 and Z 2 are independently a single bond, —O—, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —(CH 2 ) 4 — or —CH 2 CH═CHCH 2 —;
X is hydrogen, fluorine or chlorine;
Y is —CO— or —CF 2 —; and
a and b are independently 0, 1 or 2.

4. The liquid crystal composition according to claim 3 ,
wherein, in formula (1-1),
R 1 and R 2 are independently hydrogen, alkyl having 1 to 14 carbons or alkenyl having 2 to 14 carbons, and in the alkyl and the alkenyl, one or two pieces of —CH 2 — is optionally replaced by —O—, and in the groups, at least one hydrogen is optionally replaced by fluorine;
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, 1,4-phenylene, 3 -fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, pyridine-2,5-diyl or pyrimidine-2,5-diyl;
Z 1 and Z 2 are independently a single bond, —O—, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 — or —CH═CH—;
X is hydrogen or fluorine;
Y is —CO— or —CF 2 —; and
a and b are independently 0, 1 or 2, and a sum of a and b is 0, 1 or 2.

5. The liquid crystal composition according to claim 3 ,
wherein, in formula (1-1),
R 1 and R 2 are independently alkyl having 1 to 8 carbons, alkoxy having 1 to 8 carbons or alkenyl having 2 to 8 carbons;
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-phenylene or 1,4-phenylene in which at least one hydrogen is replaced by fluorine;
Z 1 and Z 2 are independently a single bond, —O—, —COO—, —OCO—, —CH 2 O—, —OCH 2 — or —CH 2 CH 2—;
X is hydrogen or fluorine;
Y is —CO— or —CF 2 —; and
a and b are independently 0, 1 or 2, and a sum of a and b is 0, 1 or 2.

6. The liquid crystal composition according to claim 1 , wherein component (a) is at least one compound selected from the group of compounds represented by formulas (1a) to (1t):

wherein, in formulas (1a) to (1),
R 1 and R 2 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons;
X is hydrogen, fluorine or chlorine; and
Y is —CO— or —CF 2 —.

7. The liquid crystal composition according to claim 1 , wherein component (a) is at least one compound selected from the group of compounds represented by formulas (1 a-1) to (1 t-1):

wherein, in formulas (1a-1) to (1t-1),
R 1 and R 2 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons; and
X is hydrogen or fluorine.

8. The liquid crystal composition according to claim 1 , wherein component (a) is at least one compound selected from the group of compounds represented by formulas (1 a-11) and (1a-12):

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Okumura Kazuo
• Masukawa Tokifumi
• Kimura Keiji

Classifications

• C07D405/08

  linked by a carbon chain containing alicyclic rings · CPC title

• C09K2019/304

  Cy-C2H4-Ph-Ph · CPC title

• C09K2019/181

  Ph-C≡C-Ph · CPC title

• C09K2019/3425

  Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems · CPC title

• C09K2019/3021

  Cy-Ph-Ph-Cy · CPC title