Liquid crystal composition and liquid crystal display device
View Patent ↗A liquid crystal composition satisfies at least one of characteristics such as a high maximum temperature of a nematic phase, a low minimum temperature of the nematic phase, small viscosity, suitable optical anisotropy, large negative dielectric anisotropy, large specific resistance, high stability to ultraviolet light and heat, or has a suitable balance regarding at least two of the characteristics. The composition contains a specific compound having high stability to ultraviolet light as a first component, and a liquid crystal display device includes the composition. The composition may contain a specific compound having large negative dielectric anisotropy as a second component, a specific compound having high maximum temperature or small viscosity as a third component, and a specific compound having a polymerizable group as an additive component.
1. A liquid crystal composition that has a negative dielectric anisotropy, and contains at least one compound represented by formula (1) as a first component:
wherein, in formula (1), R 1 , R 2 and R 3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least one of hydrogen is replaced by fluorine, in which R 2 may be hydrogen; ring A is 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, or 1,4-phenylene in which at least one of hydrogen is replaced by fluorine, chlorine or methyl; X 1 , X 2 and X 3 are independently fluorine, chlorine, or alkyl having 1 to 12 carbons in which at least one of hydrogen may be replaced by fluorine; Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—; a, b and c are independently 0, 1, 2, 3 or 4; and d is 0, 1 or 2.
2. The liquid crystal composition according to claim 1 , containing at least one compound selected from the group of compounds represented by formulas (1-1) to (1-3) as the first component:
wherein, in formula (1-1) to formula (1-3), R 1 and R 3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least one of hydrogen is replaced by fluorine; rings A 1 and A 2 are independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, or 1,4-phenylene in which at least one of hydrogen is replaced by fluorine, chlorine or methyl; X 1 , X 2 and X 3 are independently fluorine, chlorine, or alkyl having 1 to 12 carbons in which at least one of hydrogen may be replaced by fluorine; and a, b and c are independently 0, 1, 2, 3 or 4.
3. The liquid crystal composition according to claim 1 , containing at least one compound selected from the group of compounds represented by formulas (1-1-1) to (1-1-9), formula (1-2-1) and formula (1-2-2) as the first component:
wherein, in formulas (1-1-1) to (1-1-9), formula (1-2-1) and formula (1-2-2), R 1 and R 3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least one of hydrogen is replaced by fluorine.
4. The liquid crystal composition according to claim 1 , wherein a ratio of the first component is in the range of 0.03% by weight to 10% by weight based on the weight of the liquid crystal composition.
5. The liquid crystal composition according to claim 1 , containing at least one compound represented by formula (2) as a second component:
wherein, in formula (2), R 4 and R 5 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 B and ring D are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine or chlorine, or tetrahydropyran-2,5-diyl; ring C 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 5 and Z 6 are independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—; and e is 1, 2 or 3, f is 0 or 1 and a sum of e and f is 3 or less.
6. The liquid crystal composition according to claim 5 , containing at least one compound selected from the group of compounds represented by formulas (2-1) to (2-19) as the second component:
wherein, in formula (2-1) to formula (2-19), R 4 and R 5 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.
7. The liquid crystal composition according to claim 5 , wherein a ratio of the second component is in the range of 10% by weight to 90% by weight based on the weight of the liquid crystal composition.
8. The liquid crystal composition according to claim 1 , further containing at least one compound represented by formula (3) as a third component:
wherein, in formula (3), R 6 and R 7 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least one of hydrogen is replaced by fluorine; ring E and ring F are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z 7 is a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—; and g is 1, 2 or 3.
9. The liquid crystal composition according to claim 8 , containing at least one compound selected from the group of compounds represented by formulas (3-1) to (3-13) as the third component:
wherein, in formula (3-1) to formula (3-13), R 6 and R 7 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least one of hydrogen is replaced by fluorine.
10. The liquid crystal composition according to claim 8 , wherein a ratio of the third component is in the range of 10% by weight to 90% by weight based on the weight of the liquid crystal composition.
11. The liquid crystal composition according to claim 1 , containing at least one polymerizable compound represented by formula (4) as an additive component:
wherein, in formula (4), ring G and ring J 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 of hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by halogen; ring I is 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 or pyridine-2,5-diyl, and in the rings, at least one of hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by halogen; Z 8 and Z 9 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one of —CH 2 — may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one of —CH 2 —CH 2 — may be replaced by —CH═CH—, —C(CH 3 )═CH—, —CH═C(CH 3 )— or —C(CH 3 )═C(CH 3 )—, and in the groups, at least one of hydrogen may be replaced by fluorine or chlorine; P 1 , P 2 and P 3 are a polymerizable group; Sp 1 , Sp 2 and Sp 3 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one of —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, and at least one of —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one of hydrogen may be replaced by fluorine or chlorine; h is 0, 1 or 2; and j, k and m are independently 0, 1, 2, 3 or 4, and a sum of j, k and m is 1 or more.
12. The liquid crystal composition according to claim 11 , wherein in formula (4), P 1 , P 2 and P 3 are independently a polymerizable group selected from the group of groups represented by formulas (P-1) to (P-5):
wherein, in formula (P-1) to formula (P-3), M 1 , M 2 and M 3 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one of hydrogen is replaced by halogen; in formula (P-5), n 1 is 1, 2, 3 or 4; when both P 1 and P 3 are a group represented by formula (P-4), in formula (4), at least one of Sp 1 and Sp 3 is alkylene in which at least one of —CH 2 — is replaced by —O—, —COO—, —OCO— or —OCOO—.
13. The liquid crystal composition according to claim 11 , containing at least one polymerizable compound selected from the group of compounds represented by formulas (4-1) to (4-27) as the additive component:
wherein, in formula (4-1) to formula (4-27), P 4 , P 5 and P 6 are independently a group represented by formulas (P-1) to (P-3);
wherein, in formula (P-1) to formula (P-3), M 1 , M 2 and M 3 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one of hydrogen is replaced by halogen; in formula (4-1) to formula (4-27), Sp 1 , Sp 2 and Sp 3 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one of —CH 2 — may be replaced by —O—, —COO—, —OCO— or —OCOO—, and at least one of —CH 2 —CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one of hydrogen may be replaced by fluorine or chlorine.
14. The liquid crystal composition according to claim 11 , wherein a ratio of addition of the additive component is in the range of 0.03% by weight to 10% by weight, based on the weight of the liquid crystal composition before adding an additive thereto.
15. A liquid crystal display device, including the liquid crystal composition according to claim 1 .
16. The liquid crystal display device according to claim 15 , wherein an operating mode in the liquid crystal display device is an IPS mode, a VA mode, an FFS mode or an FPA mode, and a driving mode in the liquid crystal display device is an active matrix mode.
17. A polymer sustained alignment mode liquid crystal display device, wherein the liquid crystal display device includes the liquid crystal composition according to claim 11 , and a polymerizable compound in the composition is polymerized.
18. The liquid crystal composition according to claim 5 , further containing at least one compound represented by formula (3) as a third component:
wherein, in formula (3), R 6 and R 7 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least one of hydrogen is replaced by fluorine; ring E and ring F are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z 7 is a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—; and g is 1, 2 or 3.