Liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-10442992-B2
Application number	US-201615775836-A
Country	US
Kind code	B2
Filing date	Jul 6, 2016
Priority date	Dec 17, 2015
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

Abstract

A nematic liquid crystal composition has negative dielectric anisotropy and contains at least one polar compound selected from the group of compounds represented by formula (1) as a first additive, and the liquid crystal display device includes the composition. In formula (1), R 1 is hydrogen, halogen, alkyl having 1 to 12 carbons or the like; R 2 is a group represented by —OH, —OR 0 , —NH 2 , —NHR 0 or —N(R 0 ) 2 , in which R 0 is alkyl having 1 to 5 carbons; ring A and ring B are independently 1,4-cyclohexylene, 1,4-phenylene or the like; Z 1 is a single bond or the like; Sp 1 and Sp 2 are independently a single bond, alkylene having 1 to 7 carbons or the like; and a is 0 to 4.

First claim

What is claimed is:

1. A liquid crystal composition that has negative dielectric anisotropy, and contains at least one polar compound represented by formula (1) as a first additive:

wherein, in formula (1), R 1 is hydrogen, halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine; R 2 is a group represented by —OH, —OR 0 , —NH 2 , —NHR 0 or —N(R 0 ) 2 , in which R 0 is alkyl having 1 to 5 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—, and in the groups, at least one hydrogen may be replaced by fluorine; ring A and ring B are independently, 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Z 1 is a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—OCH 2 — or —CF═CF—; Sp 1 and Sp 2 are independently a single bond or alkylene having 1 to 7 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —COO— or —OCO—, and at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine; and a is 0, 1, 2, 3 or 4.

2. The liquid crystal composition according to claim 1 , wherein the first additive is at least one polar compound selected from the group of compounds represented by formula (1-1) to formula (1-9):

wherein, in formula (1-1) to formula (1-9), R′ is hydrogen, halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Z′ is a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 — or —CF═CF—; Sp 1 and Sp 2 are independently a single bond or alkylene having 1 to 7 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —COO— or —OCO—, and at least one CH 2 CH 2 — may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine; and L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 , L 10 , L 11 and L 12 are independently hydrogen, fluorine, methyl or ethyl.

3. The liquid crystal composition according to claim 1 , wherein a proportion of the first additive is in the range from 0.05% by weight to 10% by weight based on the weight of the liquid crystal composition.

4. The liquid crystal composition according to claim 1 , containing at least one compound represented by formula (2) as a first component:

wherein, in formula (2), R 3 and R 4 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkenyloxy having 2 to 12 carbons; ring C and ring E are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine, or tetrahydropyran-2,5-diyl; ring D is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochroman-2,6-diyl; Z 2 and Z 3 are independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—; and b is 1, 2 or 3, c is 0 or 1, and a sum of b and c is 3 or less.

5. The liquid crystal composition according to claim 4 , containing at least one compound selected from the group of compounds represented by formula (2-1) to formula (2-22) as the first component:

wherein, in formula (2-1) to formula (2-22), R 3 and R 4 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkenyloxy having 2 to 12 carbons.

6. The liquid crystal composition according to claim 4 , wherein a proportion of the first component is in the range from 10% by weight to 90% by weight based on the weight of the liquid crystal composition.

7. The liquid crystal composition according to claim 1 , containing at least one compound represented by formula (3) as a second component:

wherein, in formula (3), R 5 and R 6 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine; ring F and ring G are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z 4 is a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—; and d is 1, 2 or 3.

8. The liquid crystal composition according to claim 7 , containing at least one compound selected from the group of compounds represented by formula (3-1) to formula (3-13) as the second component:

wherein, in formula (3-1) to formula (3-13), R 5 and R 6 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine.

9. The liquid crystal composition according to claim 7 , wherein a proportion of the second component is in the range from 10% by weight to 70% by weight based on the weight of the liquid crystal composition.

10. The liquid crystal composition according to claim 1 , containing at least one polymerizable compound represented by formula (4) as a second additive:

wherein, in formula (4), ring J and ring P are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons,

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Saito Masayuki
• Ogita Kazuhiro
• Kondo Fumitaka

Classifications

• G02F1/1337 Primary

  Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers · CPC title

• C09K19/32

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

• C09K19/30

  containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings · CPC title

• C09K19/42 Primary

  Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 · CPC title

• C09K19/12

  at least two benzene rings directly linked, e.g. biphenyls · CPC title