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

Patent metadata

Field	Value
Publication number	US-9657229-B2
Application number	US-201414767580-A
Country	US
Kind code	B2
Filing date	Jan 27, 2014
Priority date	Feb 13, 2013
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

To provide a liquid crystal compound satisfying at least one of physical properties such as high stability to light, a high clearing point, a low minimum temperature of a liquid crystal phase, small viscosity, suitable optical anisotropy, large dielectric anisotropy, a large dielectric constant in a minor axis direction, a suitable elastic constant and excellent compatibility; a liquid crystal composition containing the compound; and a liquid crystal display device including the composition.
The compound is represented by formula (1).

For example, R 1 is alkyl having 1 to 15 carbons, ring A 1 to ring A 4 are 1,4-cyclohexylene or 1,4-phenylene, Z 1 to Z 4 are a single bond, —(CH 2 ) 2 —, —COO— or —CH 2 O—, X 1 is halogen, —C≡N, —CF 3 or —OCF 3 , L 1 and L 2 are hydrogen or fluorine, Y 1 and Y 2 are fluorine; a, b, c and d each are 0 or 1, and a sum thereof is 1 or 2.

First claim

What is claimed is:

1. A compound having a positive dielectric anisotropy represented by formula (1):

wherein, in formula (1),
R 1 is alkyl having 1 to 15 carbons, in the alkyl, at least one of —CH 2 — may be replaced by —O— or —S—, at least one of —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the groups, at least one of hydrogen may be replaced by halogen;
ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one 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 , Z 2 , Z 3 and Z 4 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 — or —CF═CF—;
X 1 is fluorine, chlorine, —C≡N, —CF 3 , —CHF 2 , —OCF 3 , —OCHF 2 , —CH═CHCF 3 , —CF═CHCF 3 , or —CF═CFCF 3 ;
L 1 is fluorine and L 2 is hydrogen or fluorine;
Y 1 and Y 2 are independently fluorine or chlorine;
a, b, c and d are independently 0 or 1, a sum of a, b, c and d is 0, 1, 2 or 3.

2. The compound according to claim 1 , wherein, in formula (1) described in claim 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) described in claim 1 , R 1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyloxy having 2 to 9 carbons.

4. The compound according to claim 1 , represented by any one of formulas (1-1) to (1-8):

wherein, in formulas (1-1) to (1-8),
R 1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons;
ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one of hydrogen is replaced by halogen, 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 ) 2 —, —COO—, —CF 2 O—, —CH 2 O— or —OCH 2 —;
X 1 is fluorine, —CF 3 or —OCF 3 ;
L 1 is fluorine and L 2 is hydrogen or fluorine; and
Y 1 and Y 2 are independently fluorine or chlorine.

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

wherein, in formulas (1-9) to (1-12),
R 1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons;
ring A 1 , ring A 2 and ring A 3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl;
X 1 is fluorine, —CF 3 or —OCF 3 ; and
L 1 is fluorine and L 2 is hydrogen or fluorine.

6. The compound according to claim 1 , represented by any one of formulas (1-13) to (1-27):

wherein, in formulas (1-13) to (1-27), R 1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons; X 1 is fluorine, —CF 3 or —OCF 3 ; and L 1 is fluorine; 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 (1-28) to (1-30):

wherein, in formulas (1-28) to (1-30), R 1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons; X 1 is fluorine, —CF 3 or —OCF 3 ; and L 1 is 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 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of hydrogen may be replaced by fluorine, and at least one 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, 2-fluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 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—, —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 of hydrogen may be replaced by fluorine, and at least one 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, 2-fluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 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 of —CH 2 — may be replaced by —O—;
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 of —CH 2 — may be replaced by —O—, and at least one 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 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

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Tanaka Hiroyuki
• Endou Hiroshi

Classifications

• C09K2019/3027

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

• C09K2019/3077

  Cy-Cy-COO-Ph · CPC title

• C09K2019/3422

  the heterocyclic ring being a six-membered ring · CPC title

• C07D493/08

  Bridged systems · CPC title

• C07D319/06

  not condensed with other rings · CPC title