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-2016200980-A1
Application number	US-201415023366-A
Country	US
Kind code	A1
Filing date	Aug 25, 2014
Priority date	Sep 19, 2013
Publication date	Jul 14, 2016
Grant date	—

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

1 . A compound, which is represented by the following formula (1):

in the formula (1):
R 1 and R 2 each independently represent hydrogen, a halogen, or an alkyl having 1 to 20 carbon atoms, in the alkyl, at least one —CH 2 — may be substituted by —O— or —S— and at least one —(CH 2 ) 2 — may be substituted by —CH═CH—, and in the groups, at least one hydrogen may be substituted by a halogen;
a ring A 1 and a ring A 2 each independently represent 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is substituted by a halogen, 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, naphthalene-2,6-diyl in which at least one hydrogen is substituted by a halogen, pyridine-2,5-diyl, or 5,5,6,6-tetrafluoro-1,3-cyclohexadiene-1,4-diyl;
Z 1 and Z 2 each independently represent a single bond or an alkylene having 1 to 4 carbon atoms, in the alkylene, at least one —CH 2 — may be substituted by —O— or —COO— and at least one —(CH 2 ) 2 — may be substituted by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be substituted by a halogen; and
a and b each independently represent 0, 1, 2, 3, or 4, a sum of a and b is 4 or less, and when a or b represents 2 or more, any two rings A 1 , any two rings A 2 , any two Z 1 's, or any two Z 2 's may be identical to or different from each other.

2 . A compound according to claim 1 , wherein, in the formula (1), Z 1 and Z 2 each independently represent a single bond, —(CH 2 ) 2 —, —CH—CH—, —CF—CF—, —CFC—, —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—.

3 . A compound according to claim 1 , wherein, in the formula (1):
R 1 and R 2 each independently represent hydrogen, fluorine, chlorine, or an alkyl having 1 to 10 carbon atoms, in the alkyl, at least one —CH 2 — may be substituted by —O— and at least one —(CH 2 ) 2 — may be substituted by —CH—CH—, and in the groups, at least one hydrogen may be substituted by fluorine or chlorine; the ring A 1 and the ring A 2 each independently represent 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is substituted by a halogen, tetrahydropyran-2,5-diyl, or 5,5,6,6-tetrafluoro-1,3-cyclohexadiene-1,4-diyl; and Z 1 and Z 2 each independently represent a single bond, —(CH 2 ) 2 —, —CH—CH—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, or —OCH 2 —.

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

5 . A compound according to claim 1 , wherein the compound is represented by any one of the following formulae (1-1) to (1-5):

in the formulae (1-1) to (1-5):
R 1 and R 2 each independently represent hydrogen, fluorine, an alkyl having 1 to 10 carbon atoms, an alkenyl having 2 to 10 carbon atoms, an alkoxy having 1 to 9 carbon atoms, or an alkenyloxy having 2 to 9 carbon atoms, and in the groups, at least one hydrogen may be substituted by fluorine;
a ring A 1 , a ring A 2 , a ring A 3 , and a ring A 4 each independently represent 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is substituted by a halogen, tetrahydropyran-2,5-diyl, or 5,5,6,6-tetrafluoro-1,3-cyclohexadiene-1,4-diyl; and
Z 1 , Z 2 , Z 3 , and Z 4 each independently represent a single bond, —(CH 2 ) 2 —, —CH═CH—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, or —OCH 2 —.

6 . A compound according to claim 5 , wherein, in the formulae (1-1) to (1-5), at least one of Z 1 , Z 2 , Z 3 , or Z 4 represents —(CH 2 ) 2 —, —CH—CH—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, or —OCH 2 —.

7 . A compound according to claim 1 , wherein the compound is represented by any one of the following formula (1-6) to formula (1-10):

in the formulae (1-6) to (1-10):
R 1 and R 2 each independently represent hydrogen, fluorine, an alkyl having 1 to 10 carbon atoms, an alkenyl having 2 to 10 carbon atoms, an alkoxy having 1 to 9 carbon atoms, or an alkenyloxy having 2 to 9 carbon atoms, and in the groups, at least one hydrogen may be substituted by fluorine; and
a ring A 1 , a ring A 2 , a ring A 3 , and a ring A 4 each independently represent 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is substituted by a halogen, tetrahydropyran-2,5-diyl, or 5,5,6,6-tetrafluoro-1,3-cyclohexadiene-1,4-diyl.

8 . A compound according to claim 7 , wherein, in the formulae (1-6) to (1-10), the ring A 1 , the ring A 2 , the ring A 3 , and the ring A 4 each independently represent 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is substituted by a halogen, or tetrahydropyran-2,5-diyl.

9 . A compound according to claim 7 , wherein the compound is represented by the formula (1-6), (1-8), or (1-10), and R 2 represents hydrogen.

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

11 . A liquid crystal composition according to claim 10 , 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, m, 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.

12 . A liquid crystal composition according to claim 10 ,
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 eac

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Yano Tomohiro

Classifications

• C09K19/0403

  the structure containing one or more specific, optionally substituted ring or ring systems · CPC title

• C09K19/3098

  Unsaturated non-aromatic rings, e.g. cyclohexene rings · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C23/18 Primary

  Polycyclic halogenated hydrocarbons · CPC title