Liquid crystal compound having tetrafluoro cyclohexadiene structure showing negative anisotropy, liquid crystal composition, and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-10221114-B2
Application number	US-201415023366-A
Country	US
Kind code	B2
Filing date	Aug 25, 2014
Priority date	Sep 19, 2013
Publication date	Mar 5, 2019
Grant date	Mar 5, 2019

Abstract

A liquid crystal compound is represented by the formula (1). For example, in the formula (1): R 1 and R 2 each represent an alkyl having 1 to 10 carbon atoms, an alkenyl having 2 to 10 carbon atoms, or an alkoxy having 1 to 9 carbon atoms; a ring A 1 and a ring A 2 each represent 1,4-cyclohexylene or 1,4-phenylene; Z 1 and Z 2 each represent a single bond, —(CH 2 ) 2 —, —CH═CH—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, or —OCH 2 —; and a and b each represent 0, 1, 2, or 3 and the sum of a and b is 4 or less.

First claim

The invention claimed is:

1. A compound of formula (1-8), formula (1-10):

in which:
R 1 represents C 3 H 7 ;
a ring A 1 , and a ring A 3 each independently represent 5,5,6,6-tetrafluoro-1,3-cyclohexadiene-1,4-diyl; and
R 2 represents hydrogen.

2. A liquid crystal composition, comprising at least one of the compounds of claim 1 .

3. A liquid crystal composition according to claim 2 , further comprising at least one compound selected from the group consisting of compounds represented by the following formulae (6) to (12):

in the formulae (6) to (12):
R 13 represents an alkyl having 1 to 10 carbon atoms or an alkenyl having 2 to 10 carbon atoms, and in the alkyl and the alkenyl, at least one —CH 2 — may be substituted by —O— and at least one hydrogen may be substituted by fluorine;
R 14 represents an alkyl having 1 to 10 carbon atoms, and in the alkyl, at least one —CH 2 — may be substituted by —O— and at least one hydrogen may be substituted by fluorine;
R 15 represents hydrogen, fluorine, an alkyl having 1 to 10 carbon atoms, or an alkenyl having 2 to 10 carbon atoms, and in the alkyl and the alkenyl, at least one —CH 2 — may be substituted by —O— and at least one hydrogen may be substituted by fluorine;
S 11 represents hydrogen or methyl;
X represents —CF 2 —, —O—, or —CHF—;
a ring D 1 , a ring D 2 , a ring D 3 , and a ring D 4 each independently represent 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one hydrogen may be substituted by fluorine, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl;
a ring D 5 and a ring D 6 each independently represent 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 each independently represent 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 each independently represent fluorine or chlorine; and
j, k, m, n, p, q, r, and s each independently represent 0 or 1, a sum of k, n, and p is 1 or 2, a sum of q, r, and s is 0, 1, 2, or 3, and t represents 1, 2, or 3.

4. A liquid crystal composition according to claim 2 , further comprising at least one compound selected from the group consisting of compounds represented by the following formulae (13) to (15):

in the formulae (13) to (15):
R 16 and R 17 each independently represent an alkyl having 1 to 10 carbon atoms or an alkenyl having 2 to 10 carbon atoms, and in the alkyl and the alkenyl, at least one —CH 2 — may be substituted by —O— and at least one hydrogen may be substituted by fluorine;
a ring E 1 , a ring E 2 , a ring E 3 , and a ring E 4 each independently represent 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5-diyl; and
Z 19 , Z 20 , and Z 21 each independently represent a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, or —COO—.

5. A liquid crystal composition according to claim 2 , further comprising at least one compound selected from the group consisting of compounds represented by the following formulae (2) to (4):

in the formulae (2) to (4):
R 11 represents an alkyl having 1 to 10 carbon atoms or an alkenyl having 2 to 10 carbon atoms, and in the alkyl and the alkenyl, at least one hydrogen may be substituted by fluorine and at least one —CH 2 — may be substituted by —O—;
X 11 represents fluorine, chlorine, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CF 2 CHF 2 , or —OCF 2 CHFCF 3 ;
a ring B 1 , a ring B 2 , and a ring B 3 each independently represent 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be substituted by fluorine, tetrahydropyran-2,5-diyl or pyrimidine-2,5-diyl;
Z 11 , Z 12 , and Z 13 each independently represent 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 each independently represent hydrogen or fluorine.

6. A liquid crystal composition according to claim 2 , further comprising at least one compound selected from the group consisting of compounds represented by the following formula (5):

in the formula (5):
R 12 represents an alkyl having 1 to 10 carbon atoms or an alkenyl having 2 to 10 carbon atoms, and in the alkyl and the alkenyl, at least one hydrogen may be substituted by fluorine and at least one —CH 2 — may be substituted by —O—;
X 12 represents —C≡N or —C≡C—C≡N;
a ring C 1 represents 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be substituted by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl;
Z 14 represents a single bond, —CH 2 CH 2 —, —C≡C—, —COO—, —CF 2 O—, —OCF 2 —, or —CH 2 O—;
L 13 and L 14 each independently represent hydrogen or fluorine; and
i represents 1, 2, 3, or 4.

7. A liquid crystal composition according to claim 2 , further comprising at least one optically active compound and/or polymerizable compound.

8. A liquid crystal composition according to claim 2 , further comprising at least one antioxidant and/or UV absorber.

9. A liquid crystal display device, comprising the liquid crystal composition of claim 2 .

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Yano Tomohiro

Classifications

• C09K2019/3009

  Cy-Ph · CPC title

• C09K2019/3004

  Cy-Cy · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C09K2019/3016

  Cy-Ph-Ph · CPC title