IP Library Granted Patent US 8,580,147
Granted Patent B2
US 8,580,147 · App. 13/496,201 · Granted Nov 12, 2013

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

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Quick Facts
Patent No.
US 8,580,147
App. No.
13/496,201
Granted
Nov 12, 2013
Kind
B2
Abstract

A liquid crystal compound represented by formula (1-1). For example, R 1 and R 2 are independently hydrogen, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons; the ring A 1 is trans-1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl; L 1 and L 2 are independently hydrogen or fluorine, and at least one of them is fluorine; and Z 1 , Z 2 and Z 3 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —C≡C—, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

Claims (67)

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

wherein R 1 and R 2 are independently hydrogen, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons;

the ring A 1 is trans-1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl;

L 1 and L 2 are independently hydrogen or fluorine, and at least one of them is fluorine; and

Z 1 , Z 2 and Z 3 are independently a single bond, —(CH 2 ) 2 —, —CH═CH—, —C≡C—, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

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

wherein R 3 and R 4 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons;

the ring A 2 is trans-1,4-cyclohexylene or 1,4-cyclohexenylene;

L 3 and L 4 are independently hydrogen or fluorine, and at least one of them is fluorine; and

Z 4 is a single bond, —(CH 2 ) 2 —, —CH═CH—, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

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

wherein R 5 and R 6 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons;

the ring A 3 is trans-1,4-cyclohexylene or 1,4-cyclohexenylene;

L 5 and L 6 are independently hydrogen or fluorine, and at least one of them is fluorine; and

Z 5 is —(CH 2 ) 2 —, —CH═CH—, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

4. The compound according to claim 1 , wherein the compound is represented by formula (1-4):

wherein R 7 and R 8 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons;

the ring A 4 is trans-1,4-cyclohexylene or 1,4-cyclohexenylene;

L 7 and L 8 are independently hydrogen or fluorine, and at least one of them is fluorine; and

Z 6 is —(CH 2 ) 2 —, —CH═CH—, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

5. The compound according to claim 2 , wherein the compound is represented by any one of formulas (1-5) and (1-6):

wherein R 3 and R 4 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons; and

Z 4 is a single bond, —(CH 2 ) 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

6. The compound according to claim 3 , wherein the compound is represented by formula (1-7):

wherein R 5 and R 6 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons; and

Z 5 is —(CH 2 ) 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

7. The compound according to claim 4 , wherein the compound is represented by any one of formulas (1-8) and (1-9):

wherein R 7 and R 8 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons; and

Z 6 is —(CH 2 ) 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

8. The compound according to claim 2 , wherein the compound is represented by formula (1-10):

wherein R 3 and R 4 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons; and

Z 4 is a single bond, —(CH 2 ) 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

9. The compound according to claim 3 , wherein the compound is represented by formula (1-11):

wherein R 5 and R 6 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons; and

Z 5 is —(CH 2 ) 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

10. The compound according to claim 4 , wherein the compound is represented by formula (1-12):

wherein R 7 and R 8 are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons; and

Z 6 is —(CH 2 ) 2 —, —CH 2 O—, —OCH 2 —, —COO— or —OCO—.

11. A liquid crystal composition comprising a compound according to claim 1 .

12. The liquid crystal composition according to claim 11 , further comprising at least one compound selected from the group of compounds represented by formulas (2), (3) and (4):

wherein R 9 is independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH 2 — may be replaced by —O—;

X 1 is fluorine, halogen, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 or —OCF 2 CHFCF 3 ;

the ring B 1 , the ring B 2 and the ring B 3 are independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 1-pyran-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 3,5-difluoro-1,4-phenylene;

Z 7 and Z 8 are independently —(CH 2 ) 2 —, —(CH 2 ) 4 —, —COO—, —OCF 2 —, —CH═CH—, —C≡C—, —CH 2 O— or a single bond; and

L 9 and L 10 are independently hydrogen or fluorine.

13. The liquid crystal composition according to claim 11 , further comprising at least one compound selected from the group of compounds represented by formula (5):

wherein R 10 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH 2 — may be replaced by —O—;

X 2 is or —C≡C—C≡N;

the ring C 1 , the ring C 2 and the ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene in which arbitrary hydrogen may be replaced by fluorine, 1,3-dioxane-2,5-diyl, 1-pyran-2,5-diyl or pyrimidine-2,5-diyl;

Z 9 is —(CH 2 ) 2 —, —COO—, —CF 2 O—, —OCF 2 —, —C≡C—, —CH 2 O— or a single bond;

L 11 and L 12 are independently hydrogen or fluorine; and

o is 0, 1 or 2, p is 0 or 1, and the sum of o; and p is 0, 1, 2 or 3.

14. The liquid crystal composition according to claim 11 , further comprising at least one compound selected from the group of compounds represented by formulas (6), (7), (8), (9), (10) and (11):

wherein 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 the alkenyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH 2 — may be replaced by —O—;

the ring D 1 , the ring D 2 , the ring D 3 and the ring D 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which arbitrary hydrogen may be replaced by fluorine, 6-pyran-2,5-diyl or decahydro-2,6-naphthalene;

Z 10 , Z 11 , Z 12 an Z 13 are independently —(CH 2 ) 2 —, —COO—, —CH 2 O—, —OCF 2 —, —OCF 2 (CH 2 ) 2 — or a single bond;

L 13 and L 14 are independently fluorine or halogen; and

q, r, s, t, u and v are independently 0 or 1, and the sum of r, s, t and u is 1 or 2.

15. The liquid crystal composition according to claim 11 , further comprising at least one compound selected from the group of compounds represented by formulas (12), (13) and (14):

wherein 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, arbitrary —CH 2 — may be replaced by —O—;

the ring E 1 , the ring E 2 and the ring E 3 are independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; and

and Z 15 are independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond.

16. The liquid crystal composition according to claim 12 , further comprising at least one compound selected from the group of compounds represented by formula (5).

17. The liquid crystal composition according to claim 14 , further comprising at least one compound selected from the group of compounds represented by formulas (12), (13) and (14).

18. The liquid crystal composition according to claim 11 , further comprising at least one optically active compound and/or at least one polymerizable compound.

19. The liquid crystal composition according to claim 11 , further comprising at least one antioxidant and/or at least one ultraviolet light absorber.

20. A liquid crystal display device comprising the liquid crystal composition according to claim 11 .

Assignments (1)
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 →