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

• US 7,758,931 B2
• Filed: 06/29/2009
• Issued: 07/20/2010
• Est. Priority Date: 03/03/2005
• Status: Active Grant

• Current Assignee: JNC Corporation (Chisso Corporation)
• Original Assignee: Chisso Corporation, Chisso Petrochemical Corporation (Chisso Corporation)
• Inventors: Sugiura, Teruyo, Shimada, Teru, Goto, Yasuyuki
• Primary Examiner(s): WU, SHEAN CHIU
• Application Number:
  US12/494,172
• Publication Number:
  US 20090264683A1
• Time in Patent Office: 386 Days
• Field of Search: 428/1.1, 252/299.63, 252/299.66, 568/647, 568/656, 570/127, 570/129, 570/182
• US Class Current: 428/1.1
• CPC Class Codes: C07C 25/13 containing fluorine
• CPC Class Codes: C07C 43/225 containing halogen
• CPC Class Codes: C09K 19/12 at least two benzene rings directly linked, e.g. biphenyls
• CPC Class Codes: C09K 19/14 linked by a carbon chain
• CPC Class Codes: C09K 19/20 linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
• CPC Class Codes: C09K 19/3003 Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
• CPC Class Codes: C09K 19/3028 in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
• CPC Class Codes: C09K 19/3066 in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
• CPC Class Codes: C09K 2019/0407 containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
• CPC Class Codes: C09K 2019/0411 containing a chlorofluoro-benzene, e.g. 2-chloro-3-fluoro-phenylene-1,4-diyl
• CPC Class Codes: C09K 2019/123 Ph-Ph-Ph
• CPC Class Codes: C09K 2019/301 Cy-Cy-Ph
• CPC Class Codes: C09K 2019/3016 Cy-Ph-Ph
• CPC Class Codes: C09K 2323/00 Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition

Abstract

Such a liquid crystal compound is provided that has stability to heat, light and so forth, has a nematic phase in a wide temperature range, has a small viscosity, a suitable optical anisotropy, and suitable elastic constants K₃₃ and K₁₁ (K₃₃: bend elastic constant, K₁₁: splay elastic constant), and has suitable negative dielectric anisotropy and excellent compatibility with other liquid crystal compounds. A liquid crystal composition containing the liquid crystal compound, and a liquid crystal display device containing the liquid crystal composition are also provided.

The liquid crystal compound is represented by one of formulas (a) to (d), the liquid crystal composition contains the liquid crystal compound, and the liquid crystal display device contains the liquid crystal composition:

wherein Ra and Rb are independently linear alkyl or linear alkoxy, rings A¹, A², B and C are independently trans-1,4-cyclohexylene or 1,4-phenylene, Z¹¹, Z¹², Z² and Z³ are independently a single bond or alkylene, and one of X₁ and X₂ is fluorine, and the other thereof is chlorine.

Claims

1. A liquid crystal compound represented by one of formulas (b) to (d):

7. A liquid crystal composition comprising the liquid crystal compound according to claim 1.

8. A liquid crystal display device comprising a liquid crystal composition comprising the liquid crystal compound according to claim 1.

2. A liquid crystal compound represented by one of formulas (b-1) to (d-1):

3. A liquid crystal compound represented by one of formulas (b-2-1) to (b-7-1):

4. The liquid crystal compound according to claim 3, wherein the compound represented by one of formulas (b-2-1) to (b-7-1), wherein Ra₂ is linear alkyl having 1 to 10 carbons, and Rb₂ is linear alkoxy having 1 to 9 carbons.

5. A liquid crystal compound represented by one of formulas (b-8-1) to (b-10-1):

6. The liquid crystal compound according to claim 5, wherein the compound represented by one of formulas (b-8-1) to (b-10-1), wherein Ra₃ is linear alkyl having 1 to 10 carbons.

9. A liquid crystal compound represented by one of formulas (b-2) to (d-2):

10. The liquid crystal compound according to claim 9, wherein the compound represented by formula (b-2), wherein Ra₁ and Rb₁ are independently linear alkyl having 1 to 10 carbons, linear alkoxy having 1 to 9 carbons, linear alkoxyalkyl having 1 to 9 carbons, linear alkenyl having 2 to 10 carbons, or linear alkenyloxy having 2 to 9 carbons, Z¹¹ is a single bond or —

(CH₂)₂— and

Z¹², Z² and Z³ are independently a single bond, —

(CH₂)₂—

, —

CH═

CH—

, —

CH₂O—

or —

OCH₂—

.

11. The liquid crystal compound according to claim 9, wherein the compound represented by formula (c-2) or (d-2), wherein Ra₁ and Rb₁ are independently linear alkyl having 1 to 10 carbons, linear alkoxy having 1 to 9 carbons, linear alkoxyalkyl having 1 to 9 carbons, or linear alkenyl having 2 to 10 carbons, and

Z¹¹ is a single bond or —

(CH₂)₂— and

Z¹², Z² and Z³ are independently a single bond, —

(CH₂)₂—

, —

CH═

CH—

, —

CH₂O—

or —

OCH₂—

.

12. The liquid crystal compound according to claim 9, wherein the compound represented by one of formulas (b-2) to (d-2), wherein Ra₁ is linear alkyl having 1 to 10 carbons or linear alkenyl having 2 to 10 carbons, Rb₁ is linear alkyl having 1 to 10 carbons or linear alkoxy having 1 to 9 carbons;

Z¹¹ is a single bond or —

(CH₂)₂— and

Z¹², Z² and Z³ are independently a single bond, —

(CH₂)₂—

, —

CH═

CH—

, —

CH₂O—

or —

OCH₂—

.

13. The liquid crystal compound according to claim 9, wherein the compound represented by one of formulas (b-2) to (d-2), wherein Z¹¹ is a single bond or —

(CH₂)₂— and

Z¹², Z² and Z³ are independently a single bond, —

(CH₂)₂—

or —

CH═

CH—

.

14. The liquid crystal compound according to claim 9, wherein the compound represented by one of formulas (b-2) to (d-2), wherein Ra₁ is linear alkyl having 1 to 10 carbons or linear alkenyl having 2 to 10 carbons, Rb₁ is linear alkoxy having 1 to 9 carbons, Z¹¹ is a single bond or —

(CH₂)₂— and

Z¹² and Z³ are independently a single bond, —

(CH₂)₂—

, —

CH═

CH—

, —

CH₂O—

or —

OCH₂—

, and Z² is —

CH₂O—

.