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

Patent metadata

Field	Value
Publication number	US-2016376503-A1
Application number	US-201515121382-A
Country	US
Kind code	A1
Filing date	Feb 4, 2015
Priority date	Feb 28, 2014
Publication date	Dec 29, 2016
Grant date	—

Abstract

Shown is a liquid crystal compound satisfying at least one of physical properties such as high stability to heat, light and so forth, a high clearing point, a low minimum temperature of a liquid crystal phase, small viscosity, suitable optical anisotropy, large negative dielectric anisotropy, a suitable elastic constant and excellent compatibility with other liquid crystal compounds. The compound is represented by formula (1).

In the formula, for example, R 1 and R 2 are alkyl having 1 to 15 carbons, and ring A 1 , ring A 2 and ring A 3 are 1,4-cyclohexylene or 1,4-cyclohexenylene, Z 1 , Z 2 and Z 3 are a single bond or —(CH 2 ) 2 —, a, b and c are 0 or 1, and a sum of a, b, and c is 0, 1 or 2.

First claim

1 . A compound represented by formula (1):

wherein, in formula (1),
R 1 and R 2 are independently alkyl having 1 to 15 carbons or alkenyl having 2 to 15 carbons, and in the groups, at least one piece of hydrogen may be replaced by halogen;
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 piece of hydrogen is replaced by halogen, or tetrahydropyran-2,5-diyl;
Z 1 , Z 2 and Z 3 independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —C≡C—, —CF═CF—, —(CH 2 ) 4 —, —CH═CH—(CH 2 ) 2 — or —(CH 2 ) 2 —CH═CH—; and
a, b and c are independently 0 or 1, and a sum of a, b and c is 0, 1 or 2.

2 . The compound according to claim 1 , wherein, in the formula (1), R 1 and R 2 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkyl having 1 to 10 carbons in which at least one piece of hydrogen is replaced by fluorine, or alkenyl having 2 to 10 carbons in which at least one piece of hydrogen is replaced by fluorine, and Z 1 , Z 2 and Z 3 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —(CH 2 ) 4 —, —CH═CH—(CH 2 ) 2 — or —(CH 2 ) 2 —CH═CH—.

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

wherein, formulas (1-1) to (1-4),
R 1 and R 2 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkyl having 1 to 10 carbons in which at least one piece of hydrogen is replaced by fluorine;
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 piece of hydrogen is replaced by fluorine, or tetrahydropyran-2,5-diyl;
Z 1 is a single bond, —(CH 2 ) 2 — or —CH═CH—;
Z 2 is a single bond, —(CH 2 ) 2 —, —(CH 2 ) 4 — or —CH═CH—(CH 2 ) 2 —; and
Z 3 is a single bond, —(CH 2 ) 2 —, —(CH 2 ) 4 — or —(CH 2 ) 2 —CH═CH—.

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

wherein, in formulas (1-5) to (1-12),
R 1 and R 2 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons; and

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 piece of hydrogen is replaced by fluorine, or tetrahydropyran-2,5-diyl.

5 . The compound according to claim 1 , represented by any one of formulas (1-13) to (1-22):

wherein, in formulas (1-13) to (1-22), R 1 and R 2 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons; and L 1 and L 2 are independently hydrogen or fluorine.

6 . The compound according to claim 1 , represented by any one of formulas (1-23) to (1-25):

wherein, in formulas (1-23) to (1-25), R 1 and R 2 are independently alkyl having 1 to 7 carbons or alkenyl having 2 to 7 carbons.

7 . A liquid crystal composition, containing at least one of compounds described in claim 1 .

8 . The liquid crystal composition according to claim 7 , 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 piece of hydrogen may be replaced by fluorine, and at least one piece 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, 2,5-difluoro-1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl 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—, —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 according to claim 7 , further containing at least one compound selected from the group of compounds represented by formula (5):

wherein, in the 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 piece of hydrogen may be replaced by fluorine, and at least one piece 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, 2,5-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 —, —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 according to claim 7 , 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 piece 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 piece of —CH 2 — may be replaced by —O—, and at least one piece 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 piece 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, 2 or 3.

11 . The liquid crystal composition according to claim 7 , further containing at least one compound selected from the group of compounds represented by formulas (13) to (15):

wherein, in formulas (13) to (15),
R 16 and R 17 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl or the alkenyl, at least one piece of —CH 2 — may be replaced by —O—, and at least one piece of hydrogen may be replaced by fluorine;
ring E 1 , ring E 2 , rin

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Tanaka Hiroyuki
• Hirata Kenji
• Yano Masakazu

Classifications

• C09K2019/122

  Ph-Ph · CPC title

• C09K19/32 Primary

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title

• C09K2019/3004

  Cy-Cy · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C09K2019/3422

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