Compound having perfluoroalkyl terminal group and CF2O bonding group, liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-9546181-B2
Application number	US-201514951104-A
Country	US
Kind code	B2
Filing date	Nov 24, 2015
Priority date	Nov 27, 2014
Publication date	Jan 17, 2017
Grant date	Jan 17, 2017

Abstract

The subject is to provide a liquid crystal compound satisfying at least one of physical properties such as a high stability to heat or light, a high clearing point (or a high maximum temperature), a low minimum temperature of a liquid crystal phase, a small viscosity, a suitable optical anisotropy, a large dielectic anisotropy, a suitable elastic constant and an excellent compatibility with any other liquid crystal compound, a liquid crystal composition including this compound and a liquid crystal display device including this composition. The compound is represented by the following formula (1a):

wherein R 1 is alkyl having 1 to 15 carbons or the like; ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-phenylene, naphthalene-2,6-diyl or the like; Z 1 and Z 2 are independently a single bond or the like; o and p are independently 0, 1 or 2; and n is an integer from 2 to 10.

First claim

What is claimed is:

1. A compound represented by formula (1a):

in formula (1a),
R 1 is alkyl having 1 to 15 carbons, and in the alkyl at least one —CH 2 — may be replaced by —O— or —S— and at least one —CH 2 CH 2 — may be replaced by —CH═CH—;
ring A 1 , ring A 2 and ring A 3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 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, pyridine-2,5-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and in these rings at least one hydrogen may be replaced by fluorine or chlorine;
ring A 4 is 1,4-phenylene or naphthalene-2,6-diyl, and in these rings at least one hydrogen may be replaced by fluorine or chlorine;
Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 — or —CF═CF—;
o and p are independently 0, 1 or 2, and the sum of o and p is 0, 1 or 2; and
n is an integer from 2 to 10.

2. The compound according to claim 1 , wherein in formula (1a) according to claim 1 , ring A 3 is 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine, naphthalene-2,6-diyl or naphthalene-2,6-diyl in which at least one hydrogen has been replaced by fluorine or chlorine.

3. The compound according to claim 1 , wherein the compound is represented by formula (1b):

in formula (1b),
R 1 is alkyl having 1 to 15 carbons, and in the alkyl at least one —CH 2 — may be replaced by —O— and at least one —CH 2 CH 2 — may be replaced by —CH═CH—;
ring A 1 is 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at least one hydrogen has been replaced by fluorine or chlorine, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl or 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl;
ring A 2 is 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine, naphthalene-2,6-diyl or naphthalene-2,6-diyl in which at least one hydrogen has been replaced by fluorine or chlorine;
ring A 3 is 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine, naphthalene-2,6-diyl or naphthalene-2,6-diyl in which at least one hydrogen has been replaced by fluorine or chlorine;
Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 — or —CF═CF—;
L 1 and L 2 are independently hydrogen, fluorine or chlorine;
o and p are independently 0, 1 or 2, and the sum of o and p is 0, 1 or 2; and
n is an integer from 2 to 10.

4. The compound according to claim 3 , wherein in formula (1b) according to claim 3 , R 1 is alkyl having 1 to 15 carbons, alkoxy having 1 to 14 carbons, alkenyl having 2 to 15 carbons or alkenyloxy having 2 to 14 carbons; and Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —CF 2 O— or —COO—.

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

in formulas (1-1) to (1-4),
R 1 is alkyl having 1 to 15 carbons, alkoxy having 1 to 14 carbons, alkenyl having 2 to 15 carbons or alkenyloxy having 2 to 14 carbons;
ring A 1 is 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at least one hydrogen has been replaced by fluorine or chlorine, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl;
ring A 2 is 1,4-cyclohexylene, 1,4-phenylene or 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine, naphthalene-2,6-diyl or naphthalene-2,6-diyl in which at least one hydrogen has been replaced by fluorine or chlorine;
ring A 3 is 1,4-phenylene or 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine, naphthalene-2,6-diyl or naphthalene-2,6-diyl in which at least one hydrogen has been replaced by fluorine or chlorine;
Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 — or —CH═CH—;
L 1 and L 2 are independently hydrogen or fluorine; and
n is an integer from 2 to 10.

6. The compound according to claim 5 , wherein in formulas (1-1) to (1-4) according to claim 5 , R 1 is alkyl having 1 to 15 carbons or alkenyl having 2 to 15 carbons.

7. The compound according to claim 1 , wherein the compound is represented by any one of formulas (1-5) to (1-37):

in formulas (1-5) to (1-37), R 1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons; L 1 and L 2 are independently hydrogen or fluorine; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 are independently hydrogen or fluorine; Z 1 is a single bond, —CH 2 CH 2 — or —CH═CH—; and n is an integer from 2 to 10.

8. The compound according to claim 1 , wherein the compound is represented by any one of formulas (1-38) to (1-45):

in formulas (1-38) to (1-45), R 1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons; L 1 and L 2 are independently hydrogen or fluorine; Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are independently hydrogen or fluorine; and n is an integer from 2 to 10.

9. The compound according to claim 8 , wherein in formulas (1-38) to (1-45) according to claim 8 , R 1 is alkyl having 1 to 10 carbons; L 1 and L 2 are fluorine; and Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 are independently hydrogen or fluorine.

10. A liquid crystal composition including at least one of compounds according to claim 1 .

11. The liquid crystal composition according to claim 10 , further including at least one compound selected from the group of compounds represented by formulas (2) to (4):

in formulas (2) to (4),
R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl at least one —CH 2 — may be replaced by —O— and at least one hydrogen may be replaced by 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—.

12. The liquid crystal composition according to claim 10 , further including at least one compound selected from the group of compounds represented by formulas (5) to (7):

in formula (5) to (7),
R 13 is alkyl having 1 to

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Fujimori Sayaka
• Tanaka Hiroyuki

Classifications

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K19/3402

  having oxygen as hetero atom (sugars C09K19/0422) · CPC title

• C07D309/06

  Radicals substituted by oxygen atoms · CPC title

• C09K2019/3071

  Cy-Cy-COO-Cy · CPC title

• C09K19/3068

  chain containing -COO- or -OCO- groups · CPC title