IP Library Granted Patent US 8,685,274
Granted Patent B2
US 8,685,274 · App. 13/157,908 · Granted Apr 1, 2014

Compound having a five-membered ring, the liquid crystal composition and the liquid crystal display device

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Quick Facts
Patent No.
US 8,685,274
App. No.
13/157,908
Granted
Apr 1, 2014
Kind
B2
Abstract

The invention provides a liquid crystal compound that has an excellent compatibility with other liquid crystal compounds and also has at least one of characteristics such as a high stability to heat, light or the like, a suitable refractive index anisotropy (Δn), a low threshold voltage and a suitable dielectric anisotropy (Δ∈). A compound represented by formula (1). For example, R 1 is alkyl having 1 to 10 carbons, R 2 is halogen or alkenyl having 2 to 10 carbons; the ring A 1 , the ring A 2 and the ring A 3 are 1,4-cyclohexylene or 1,4-phenylene; Z 1 , Z 2 and Z 3 are a single bond or alkylene having 1 to 4 carbons; G is —CH 2 — or —O—; and m is 1, and n and p is 0 or 1.

Claims (70)

1. A compound represented by formula (1):

wherein

R 1 is alkyl having 1 to 10 carbons, and in the alkyl, arbitrary —CH 2 — may be replaced by —O— and arbitrary —(CH 2 ) 2 — may be replaced by —CH═CH—;

R 2 is alkenyl having 2 to 10 carbons;

the ring A 1 , the ring A 2 and the ring A 3 are each independently 1,4-cyclohexylene or 1,4-phenylene;

Z 1 , Z 2 and Z 3 are each independently a single bond, —(CH 2 ) 2 —, —(CH 2 ) 4 —, —COO—, —OCO—, —CH═CH—, —CF═CF—, —CH 2 O— or —OCH 2 —;

G is —CH 2 ; and

m, n and p are each independently 0 or 1, and the sum of m, n and p is 1, 2 or 3.

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

R 1 is alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyl having 2 to 10 carbons;

and

Z 1 , Z 2 and Z 3 are each independently a single bond, —(CH 2 ) 2 —, —(CH 2 ) 4 —.

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

R 1 is alkyl having 1 to 7 carbons, alkoxy having 1 to 6 carbons or alkenyl having 2 to 7 carbons; R 2 is alkenyl having 2 to 7 carbons;

and

Z 1 , Z 2 and Z 3 are a single bond.

4. A liquid crystal composition comprising a first component and a second component, wherein the first component is at least one compound selected from the compounds according to claim 1 .

5. The liquid crystal composition according to claim 4 , wherein the second component is at least one compound selected from the group of compounds represented by formulas (2), (3) and (4):

wherein

R 3 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 1 is fluorine, chlorine, —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 each independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 1-tetrahydropyran-2,5-diyl, or 1,4-phenylene in which arbitrary hydrogen may be replaced by fluorine;

Z 4 and Z 5 are each independently —(CH 2 ) 2 —, —(CH 2 ) 4 —, —COO—, —CF 2 O—, —OCF 2 —, —CH═CH—, —C≡C—, —CH 2 O— or a single bond; and

L 1 and L 2 are each independently hydrogen or fluorine.

6. The liquid crystal composition according to claim 4 , wherein the second component is at least one compound selected from the group of compounds represented by formula (5):

wherein

R 4 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 —C≡N or —C≡C—CN;

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

Z 6 is —(CH 2 ) 2 —, —COO—, —CF 2 O—, —OCF 2 —, —C≡C—, —CH 2 O— or a single bond;

L 3 and L 4 are each independently hydrogen or fluorine; and

q is 0, 1 or 2, and r is 0 or 1.

7. The liquid crystal composition according to claim 4 , wherein the second component is at least one compound selected from the group of compounds represented by formulas (6), (7), (8), (9), (10) and (11):

wherein

R 5 and R 6 are each independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, in the alkyl and the alkenyl, arbitrary —CH 2 — may be replaced by —O—, and in the alkenyl, arbitrary hydrogen may be replaced by fluorine;

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

Z 7 , Z 8 , Z 9 and Z 10 are each independently —(CH 2 ) 2 —, —COO—, —CH 2 O—, —OCF 2 —, —OCF 2 (CH 2 ) 2 — or a single bond;

L 5 and L 6 are each independently fluorine or chlorine; and

j, k, l, s, t and u are each independently 0 or 1, and the sum of k, l, s and t is 1 or 2.

8. The liquid crystal composition according to claim 4 , wherein the second component is at least one compound selected from the group of compounds represented by formulas (12), (13) and (14):

wherein

R 7 and R 8 are each 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—, and in the alkenyl, arbitrary hydrogen may be replaced by fluorine;

the ring E 1 , the ring E 2 and the ring E 3 are each 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

Z 11 and Z 12 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond.

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

wherein

R 4 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 —C≡N or —C≡C—CN;

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

Z 6 is —(CH 2 ) 2 —, —COO—, —CF 2 O—, —OCF 2 —, —C≡C—, —CH 2 O— or a single bond;

L 3 and L 4 are each independently hydrogen or fluorine; and

q is 0, 1 or 2, and r is 0 or 1.

10. The liquid crystal composition according to claim 5 , further comprising at least one compound selected from the group of compounds represented by formulas (12), (13) and (14):

wherein

R 7 and R 8 are each 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—, and in the alkenyl, arbitrary hydrogen may be replaced by fluorine;

the ring E 1 , the ring E 2 and the ring E 3 are each 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

Z 11 and Z 12 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond.

11. The liquid crystal composition according to claim 6 , further comprising at least one compound selected from the group of compounds represented by formulas (12), (13) and (14):

wherein

R 7 and R 8 are each 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—, and in the alkenyl, arbitrary hydrogen may be replaced by fluorine;

the ring E 1 , the ring E 2 and the ring E 3 are each 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

Z 11 and Z 12 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond.

12. The liquid crystal composition according to claim 7 , further comprising at least one compound selected from the group of compounds represented by formulas (12), (13) and (14):

wherein

R 7 and R 8 are each 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—, and in the alkenyl, arbitrary hydrogen may be replaced by fluorine;

the ring E 1 , the ring E 2 and the ring E 3 are each 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

Z 11 and Z 12 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond.

13. The liquid crystal composition according to claim 4 , further comprising at least one optically active compound and/or at least one polymerizable compound.

14. The liquid crystal composition according to claim 4 , wherein further comprising at least one antioxidant and/or at least one ultraviolet light absorber.

15. A liquid crystal display device containing the liquid crystal composition according to claim 4 .

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 →