IP Library Granted Patent US 10,308,871
Granted Patent B2
US 10,308,871 · App. 15/547,063 · Granted Jun 4, 2019

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

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,308,871
App. No.
15/547,063
Granted
Jun 4, 2019
Kind
B2
Abstract

Provided is a liquid crystal compound that has high stability to heat, light and so forth, a high clearing point, 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, a liquid crystal composition containing the compound and a liquid crystal display device including the composition. The compound is represented by formula (1). For example, R 1 is alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyl having 2 to 10 carbons; R 2 is alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyl having 3 to 10 carbons; ring A 1 is 1,4-cyclohexylene or 1,4-phenylene; ring A 2 is 1,4-cyclohexylene or 1,4-phenylene; Z 1 and Z 2 are a single bond; Z 3 is —O— or a single bond; and L 1 is F, CF 3 or CF 2 H.

Claims (61)

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

wherein, in formula (1),

R 1 and R 2 are independently hydrogen, halogen or alkyl having 1 to 20 carbons, and in the alkyl, at least one piece of —CH 2 — may be replaced by —O— or —S—, at least one piece of —(CH 2 ) 2 — may replace by —CH═CH—, and in the groups, at least one piece of hydrogen may be replaced by halogen;

ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, or pyridine-2,5-diyl, and at least one piece of hydrogen on the rings may be replaced by halogen;

Z 1 and Z 2 are independently a single bond or alkylene having 1 to 4 carbons, in the alkylene, at least one piece of —CH 2 — may be replaced by —O— or —COO—, and at least one piece of —(CH 2 ) 2 — may replace by —CH=CH— or —C≡C—, and in the groups, at least one piece of hydrogen may be replaced by halogen;

Z 3 is —O— or a single bond;

L 1 is F, CF 3 or CF 2 H; and

a and b are independently 0, 1, 2, 3 or 4, and a sum of a and b is 4 or less, and when a or b is 2 or more, two of arbitrary ring A 1 , two of arbitrary ring A 2 , two pieces of arbitrary Z 1 or two pieces of arbitrary Z 2 may be identical or different.

2. The compound according to claim 1 , represented by formula (1-2):

wherein, in formula (1-2),

R 1 and R 2 are independently hydrogen, halogen or alkyl having 1 to 20 carbons, and in the alkyl, at least one piece of —CH 2 — may be replaced by —O— or —S—, at least one piece of —(CH 2 ) 2 — may replace by —CH═CH—, and in the groups, at least one piece of hydrogen may be replaced by halogen;

ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, or pyridine-2,5-diyl, and at least one piece of hydrogen on the rings may be replaced by halogen;

Z 1 and Z 2 are independently a single bond or alkylene having 1 to 4 carbons, in the alkylene, at least one piece of —CH 2 — may be replaced by —O— or —COO—, and at least one piece of —(CH 2 ) 2 — may replace by —CH═CH— or and in the groups, at least one piece of hydrogen may be replaced by halogen;

Z 3 is —O— or a single bond; and

a and b are independently 0, 1, 2, 3 or 4, and a sum of a and b is 4 or less, and when a or b is 2 or more, two of ring A′ and A 2 , and two of Z 1 and Z 2 may be identical or different.

3. The compound according to claim 2 , wherein, in formula (1-2), R 1 and R 2 are independently chlorine, fluorine, alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkenyl having 2 to 10 carbons, polyfluoroalkyl having 1 to 10 carbons or polyfluoroalkyl having 1 to 9 carbons;

ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one piece of hydrogen may be replaced by halogen, or tetrahydropyran-2,5-diyl;

Z 1 and Z 2 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —CF═CF—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —(CH 2 ) 4 —, —(CH 2 ) 2 CF 2 O—, —(CH 2 ) 2 OCF 2-5 —CF 2 O(CH 2 ) 2 —, —OCF 2 (CH 2 ) 2 —CH═CH—(CH 2 ) 2 — or —(CH 2 ) 2 —CH═CH—; and

a and b are independently 0, 1, 2, 3 or 4, and a sum of a and b is 4 or less.

4. The compound according to claim 2 , wherein, in formula (1-2), a sum of a and b is 0, 1, 2 or 3;

R 1 and R 2 are independently chlorine, fluorine, alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkenyl having 2 to 10 carbons, polyfluoroalkyl having 1 to 10 carbons or polyfluoroalkyl having 1 to 9 carbons;

ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one piece of hydrogen may be replaced by halogen, tetrahydropyran-2,5-diyl; and

Z 1 and Z 2 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —(CH 2 ) 4 —, —(CH 2 ) 2 CF 2 O—, —(CH 2 ) 2 OCF 2 —CF 2 O(CH 2 ) 2 —, —OCF 2 (CH 2 ) 2 —CH═CH—(CH 2 ) 2 — or —(CH 2 ) 2 —CH═CH—.

5. The compound according to claim 1 , represented by any one of formulas (1-2-1) to (1-2-10):

wherein, in formulas (1-2-1) to (1-2-10), R 1 and R 2 are independently chlorine, fluorine, alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkenyl having 2 to 10 carbons, polyfluoroalkyl having 1 to 10 carbons or polyfluoroalkyl having 1 to 9 carbons;

ring A 1 , ring A 2 , ring A 3 and ring A 4 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; and

Z 1 , Z 2 , Z 4 and Z 5 are independently a single bond, —(CH 2 ) 2 —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —(CH 2 ) 4 —, —(CH 2 ) 2 CF 2 O—, —(CH 2 ) 2 OCF 2 —CF 2 O(CH 2 ) 2 —, —OCF 2 (CH 2 ) 2 —CH═CH—(CH 2 ) 2 — or —(CH 2 ) 2 —CH═CH—.

6. The compound according to claim 5 , wherein, in formulas (1-2-1) to (1-2-10), R 1 and R 2 are independently fluorine, alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkenyl having 2 to 10 carbons or polyfluoroalkyl having 1 to 9 carbons;

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

Z 1 , Z 2 , Z 4 and Z 5 are independently a single bond, —(CH 2 ) 2 —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O— or —OCH 2 —.

7. The compound according to claim 6 , represented by any one of formulas (1-2-4), (1-2-7) and (1-2-9):

8. The compound according to claim 6 , represented by any one of formulas (1-2-1), (1-2-5), (1-2-8) and (1-2-10), wherein, R 1 is alkoxy having 1 to 6 carbons:

9. A liquid crystal composition, containing at least one compound according to claim 1 .

10. The liquid crystal composition according to claim 9 , 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 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 —CH 2 — may be replaced by —O—, and at least one piece of hydrogen may be replaced by fluorine;

R 14 is alkyl having 1 to 10 carbons, in the alkyl, 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 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 —, —OCO—, —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, and 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 9 , 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 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;

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 9 , 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 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

L 11 and L 12 are independently hydrogen or fluorine.

13. The liquid crystal composition according to claim 9 , further containing at least one optically active compound and/or at least one polymerizable compound.

14. The liquid crystal composition according to claim 9 , further containing at least one antioxidant and/or at least one ultraviolet light absorbent.

15. A liquid crystal display device, including the liquid crystal composition according to claim 9 .

16. A liquid crystal display device, wherein the liquid crystal composition according to claim 9 is encapsulated.

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 Aug 4, 2017
From: YANO, TOMOHIRO
To: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
Reel/Frame 043194/0959 →
Cited By (2)
US 12,195,454 US 12,377,152