IP Library Granted Patent US 9,879,183
Granted Patent B2
US 9,879,183 · App. 15/317,412 · Granted Jan 30, 2018

Liquid crystal compound having CF

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Quick Facts
Patent No.
US 9,879,183
App. No.
15/317,412
Granted
Jan 30, 2018
Kind
B2
Abstract

To show a liquid crystal compound satisfying at least one of physical properties such as high chemical stability, a high clearing point, a low minimum temperature of a liquid crystal phase, low viscosity, large optical anisotropy, large dielectric anisotropy, a suitable elastic constant and excellent compatibility with other liquid crystal compounds, a liquid crystal composition containing the compound and a liquid crystal display device including the composition. A compound is represented by formula (1).

Claims (62)

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

wherein, in formula (1),

R 1 is alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —CH 2 — may be replaced by —O—, and at least one piece of —CH 2 CH 2 — may be replaced by —CH═CH—, 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, 2-halogeno-1,4-phenylene, 2,6-dihalogeno-1,4-phenylene, pyrimidine-2,5-diyl or pyridine-2,5-diyl;

Z 1 and Z 2 are independently a single bond or—C≡C—, but at least one is —C≡C—;

L 1 is halogen, —OCF 3 or —CF 3 ;

L 2 and L 3 are independently hydrogen or halogen, but at least one is halogen; and

m and n are independently 0, 1 or 2, and a sum of m and n is 1 or 2.

2. The compound according to claim 1 , wherein in formula (1)

R 1 is alkyl having 1 to 15 carbons, alkenyl having 2 to 15 carbons, alkoxy having 2 to 15 carbons, alkyl having 1 to 15 carbons in which at least one piece of hydrogen is replaced by halogen, alkenyl having 2 to 15 carbons in which at least one piece of hydrogen is replaced by halogen, or alkoxy having 2 to 15 carbons in which at least one piece of hydrogen is replaced by halogen;

ring A 1 , ring A 2 and ring A 3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 2-halogeno-1,4-phenylene, 2,6-dihalogeno-1,4-phenylene, pyrimidine-2,5-diyl or pyridine-2,5-diyl;

Z 1 and Z 2 are independently a single bond or —C≡C—, and at least one of m pieces of Z 1 and n pieces of Z 2 is —C≡C—;

L 1 is halogen, —OCF 3 or —CF 3 ;

L 2 and L 3 are independently hydrogen or halogen, but at least one is halogen; and

m and n are independently 0, 1 or 2, and a sum of m and n is 1 or 2.

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

wherein, in formulas (1-1) to (1-3),

R 1 is alkyl having 1 to 15 carbons, alkenyl having 2 to 15 carbons, alkoxy having 1 to 14 carbons or alkenyloxy having 2 to 14 carbons;

ring A 1 , ring A 2 and ring A 3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 2-halogeno-1,4-phenylene, 2,6-dihalogeno-1,4-phenylene, pyrimidine-2,5-diyl or pyridine-2,5-diyl;

Z 1 and Z 2 are independently a single bond or —C≡C—, and at least one of m pieces of Z 1 and n pieces of Z 2 is —C≡C—;

L 1 is halogen, —OCF 3 or —CF 3 ; and

L 2 and L 3 are independently hydrogen or fluorine, and at least one is fluorine.

4. The compound according to claim 3 , wherein, in formulas (1-1) to (1-3), ring A 1 , ring A 2 and ring A 3 are independently 1,4-phenylene, 2-halogeno-1,4-phenylene, 2,6-dihalogeno-1,4-phenylene, pyrimidine-2,5-diyl or pyridine-2,5-diyl; and L 1 is fluorine, —OCF 3 or —CF 3 .

5. The compound according to claim 1 , represented by any one of formulas (1-4) to (1-28):

wherein, in formulas (1-4) to (1-28), R 1 is alkyl having 1 to 15 carbons, alkenyl having 2 to 15 carbons, alkoxy having 1 to 14 carbons or alkenyloxy having 2 to 14 carbons; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , and Y 6 are independently hydrogen, fluorine or chlorine; L 1 is fluorine, chlorine, —OCF 3 or —CF 3 ; and L 2 and L 3 are independently hydrogen or fluorine, but at least one is fluorine.

6. The compound according to claim 5 , wherein, in formulas (1-4) to (1-28), L 1 is fluorine or —CF 3 .

7. A liquid crystal composition, containing at least one compound according to 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 oralkenyl 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 , or —OCF 2 CHFCF 3 ;

ring B 1 , ring B 2 and ring B 3 are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one piece of hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

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 when any one of Z 11 , Z 12 and Z 13 is —CF 2 O—, others are a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCF 2 —, —CH 2 O— or —(CH 2 ) 4 —, and when any one of Z 11 , Z 12 and Z 13 is —CF 2 O—, others are a single bond, —CH 2 CH 2 —, —CH═CH—, —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 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 is —C≡N or —C≡C—C≡N;

ring C 1 is 1,4-cyclohexylene, 1,4-phenylene in which at least one piece of hydrogen may be replaced by fluorine, 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 —, —C≡C—, —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—, and at least one piece of hydrogen may be replaced by fluorine;

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 13 and X 14 are independently —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 , ring E 3 and ring E 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 19 , Z 20 and Z 21 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C— or —COO—.

12. The liquid crystal composition according to claim 7 , further containing at least one of a polymerizable compound, an optically active compound, an antioxidant, an ultraviolet light absorber, a light stabilizer, a heat stabilizer and an antifoaming agent.

13. A liquid crystal display device, including the liquid crystal composition according to claim 7 .

14. The liquid crystal display device according to claim 13 , wherein the liquid crystal composition is encapsulated.

15. The liquid crystal display device according to claim 13 , wherein the liquid crystal composition is used in a lens to be utilized for switching between 2D and 3D.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2025
From: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
To: JIANGSU HECHENG DISPLAY TECHNOLOGY CO., LTD.
Reel/Frame 072472/0393 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2016
From: TAKAHASHI, MICHIKO; FUJIMORI, SAYAKA; SASADA, YASUYUKI
To: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
Reel/Frame 040653/0981 →