Liquid crystal compound having vinylene group, liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-10155905-B2
Application number	US-201615046452-A
Country	US
Kind code	B2
Filing date	Feb 18, 2016
Priority date	Feb 24, 2015
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

Abstract

A compound is represented by formula (1).

In formula (1), R 1 is hydrogen, fluorine, 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, —COO— or the like; X 1 is hydrogen, fluorine, —CF 3 , or —OCF 3 ; L 1 and L 2 are independently hydrogen or fluorine; and a is 0 or 1, and b is 0 or 1.

First claim

What is claimed is:

1. A compound represented by formula (1-g),

wherein in formula (1-g),
R 1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, wherein at least one —CH 2 — in the alkyl or alkenyl is optionally replaced with —O—;
X 1 is hydrogen, fluorine, —CF 3 , or —OCF 3 ; and
L 1 , L 2 , L 3 and L 4 are independently hydrogen or fluorine, wherein at least one of L 1 and L 2 is fluorine.

2. The compound of claim 1 , represented by any one of formulae (1-k) to (1-m),

wherein in formulae (1-k) to (1-m),
R 1 is alkyl having 1 to 5 carbons or alkenyl having 2 to 5 carbons, wherein at least one —CH 2 — in the alkyl or alkenyl is optionally replaced with —O—;
X 1 is hydrogen, fluorine, —CF 3 , or —OCF 3 ; and
L 1 and L 2 are independently hydrogen or fluorine, wherein at least one of L 1 and L 2 is fluorine.

3. The compound of claim 2 , wherein in formulae (1-k) to (1-m) of claim 2 , R 1 is alkyl having 1 to 5 carbons or alkenyl having 2 to 5 carbons; X 1 is fluorine; and L 1 and L 2 are independently hydrogen or fluorine, wherein at least one of L 1 and L 2 is fluorine.

4. The compound of claim 2 , wherein in formulae (1-k) to (1-m) of claim 2 , R 1 is alkyl having 1 to 5 carbons or alkenyl having 2 to 5 carbons; X 1 is —CF 3 ; and L 1 and L 2 are independently hydrogen or fluorine, wherein at least one of L 1 and L 2 is fluorine.

5. The compound of claim 2 , wherein in formulae (1-k) to (1-m) of claim 2 , R 1 is alkyl having 1 to 5 carbons or alkenyl having 2 to 5 carbons; X 1 is —OCF 3 ; and L 1 and L 2 are independently hydrogen or fluorine, wherein at least one of L 1 and L 2 is fluorine.

6. A liquid crystal composition containing at least one compound of claim 1 .

7. The liquid crystal composition of claim 6 , further containing at least one compound selected from the group consisting of compounds represented by formulae (2) to (4),

wherein in formulae (2) to (4),
R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, wherein at least one —CH 2 — in the alkyl or alkenyl is optionally replaced with —O—, and at least one hydrogen in the alkyl or alkenyl is optionally replaced with 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, —CH 2 CH 2 —, —CH═CH—, —C≡C—, or —COO—.

8. The liquid crystal composition of claim 6 , further containing at least one compound selected from the group consisting of compounds represented by formulae (5) to (7),

wherein in formulae (5) to (7),
R 13 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, wherein at least one —CH 2 — in the alkyl and alkenyl is optionally replaced with —O—, and at least one hydrogen in the alkyl and alkenyl is optionally replaced with 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 in which at least one hydrogen is optionally replaced with 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, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, or —(CH 2 ) 4 —; and
L 11 and L 12 are independently hydrogen or fluorine.

9. The liquid crystal composition of claim 6 , further containing at least one compound represented by formula (8),

wherein in formula (8),
R 14 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, wherein at least one —CH 2 — in the alkyl and alkenyl is optionally replaced with —O—, and at least one hydrogen in the alkyl and alkenyl is optionally replaced with fluorine;
X 12 is —C≡N or —C≡C—C≡N;
ring D 1 is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen is optionally replaced with fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl;
Z 17 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.

10. The liquid crystal composition of claim 6 , further containing at least one compound selected from the group consisting of compounds represented by formulae (9) to (15),

wherein in formulae (9) to (15),
R 15 and R 16 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, wherein at least one —CH 2 — in the alkyl and alkenyl is optionally replaced with —O—, and at least one hydrogen in the alkyl and alkenyl is optionally replaced with fluorine;
R 17 is hydrogen, fluorine, alkyl having 1 to 10 carbons, or alkenyl having 2 to 10 carbons, wherein at least one —CH 2 — in the alkyl and alkenyl is optionally replaced with —O—, and at least one hydrogen in the alkyl and alkenyl is optionally replaced with 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 in which at least one hydrogen is optionally replaced with 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 18 , Z 19 , Z 20 , and Z 21 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;
S 11 is hydrogen or methyl;
X is —CHF— or —CF 2 —; and
j, k, m, n, p, q, r and s are independently 0 or 1, the sum of k, m, n and p is 1 or 2, the sum of q, r and s is 0, 1, 2, or 3, and t is 1, 2, or 3.

11. The liquid crystal composition of claim 6 , further containing at least one of a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorbent, a light stabilizer, a heat stabilizer, a dye and a defoamer.

12. A liquid crystal display device, containing the liquid crystal composition of claim 6 .

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Gotoh Yasuyuki
• Kimura Keiji

Classifications

• C07D213/68

  attached in position 4 · CPC title

• C09K2019/3083

  Cy-Ph-COO-Ph · CPC title

• C07D309/06

  Radicals substituted by oxygen atoms · CPC title

• C07D239/28

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms · CPC title

• C09K19/3048

  in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds · CPC title