Chroman dervative and liquid-crystal composition containing the compound

• US 20060163536A1
• Filed: 06/25/2004
• Published: 07/27/2006
• Est. Priority Date: 06/30/2003
• Status: Active Grant

• Current Assignee: Dainippon Ink and Chemicals Incorporated
• Original Assignee: Dainippon Ink and Chemicals Incorporated
• Inventors: Matsumoto, Takashi, Kusumoto, Tetsuo, Kawakami, Shotaro
• Granted Patent: US 7,226,644 B2
• Time in Patent Office: Days
• US Class Current: 252/299.610
• CPC Class Codes: C09K 19/3402 having oxygen as hetero atom sugars C09K19/0422
• CPC Class Codes: C09K 2019/3425 Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems
• CPC Class Codes: C09K 2323/00 Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
• CPC Class Codes: C09K 2323/03 Viewing layer characterised by chemical composition

Abstract

The present invention relates to a liquid crystal compound which has negative dielectric anisotropy and a large absolute value thereof; and a liquid crystal display element which contains the compound as a constituent element and has a negative value of dielectric anisotropy in the vertical alignment mode, IPS, or the like. The liquid-crystal display element has a structure including a pair of substrates and a liquid crystal sandwiched therebetween, and includes at least an alignment control layer, a transparent electrode, and a polarizing plate, in which the liquid crystal includes at least one compound having a partial structure represented by general formula (A):
(wherein W¹ and W² each independently represents fluorine, chlorine, —CF₃, —CF₂H, —OCF₃, or —OCF₂H) and has negative dielectric anistropy.

Claims

1. A liquid crystal display element:

having a structure comprising a pair of substrates, and a liquid crystal composition sandwiched between the substrates;

comprising at least an alignment control layer, a transparent electrode, and a polarizing plate; and

characterized in that the liquid crystal composition comprises at least one liquid crystal compound having a partial structure represented by general formula (A);

(wherein W¹ and W² each independently represents fluorine, chlorine, —

CF₃, —

CF₂H, —

OCF₃, or —

OCF₂H) and has a negative dielectric anistropy.

2. A liquid crystal display element according to claim 1, wherein W¹ and W² represent fluorine in the general formula (A).

16. A liquid crystal display element according to claim 1, comprising at least one compound represented by the general formula (2) according to claim 15.

20. A liquid crystal display element according to claim 1, wherein the liquid crystal display element has an active matrix drive system.

21. A liquid crystal display element according to claim 1, wherein the liquid crystal display element has a liquid crystal alignment regulated by the alignment control layer to be vertical to a surface of the substrate.

3. A compound represented by general formula (1):

4. A compound according to claim 3, wherein R¹ and R² each independently represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms (in which one CH₂ group may be substituted by oxygen), and W¹ and W² represent fluorine in the general formula (1).

5. A compound according to claim 3, wherein A¹, A², A³ and A⁴ each independently represents a trans1,4-cyclohexylene group, a 1,4-phenylene group which may be substituted by at least one fluorine, or a 1,4-bicyclo[2.2.2]octylene group in the general formula (1).

6. A compound according to claim 3, wherein Z¹, Z², Z³, and Z⁴ each independently represents —

CH₂CH₂—

, —

CH═

CH—

, —

CF₂CF₂—

, —

CF═

CF—

, —

CH₂O—

, —

OCH₂—

, —

C≡

C—

, —

CF₂O—

, —

OCF₂—

or a single bond in the general formula (1).

7. A compound according to claim 3, wherein the sum of a, b, c, and d is 1 or 2 in the general formula (1).

8. A compound according to claim 3, wherein R¹ and R² each independently represents an alkyl group having 1 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms (in which a CH₂ group may be substituted by oxygen), W¹ and W² represent fluorine, A¹, A², A³, and A⁴ each independently represents a trans-1,4-cyclohexylene group, a 1,4-phenylene group which may be substituted by at least one fluorine, or a 1,4-bicyclo[2.2.2]octylene group, Z¹, Z², Z³ and Z⁴ each independently represents —

CH₂CH₂—

, —

CH═

CH—

, —

CF₂CF₂—

, —

CF═

CF—

, —

CH₂O—

, —

OCH₂—

, —

C≡

C—

, —

CF₂O—

, —

OCF₂—

, or a single bond, and the sum of a, b, c, and d is 1 or 2 in the general formula (1).

9. A compound according to claim 3, wherein R¹ and R² each independently represents an alkyl group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkoxyl group having 1 to 7 carbon atoms, A¹, A², A³, and A⁴ each independently represents a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, or a 2,3-difluoro-1,4-phenylene group, Z¹, Z², Z³, and Z⁴ each independently represents —

CH₂CH₂—

, —

CH₂O—

, —

OCH₂—

, or a single bond, W¹ and W² represent fluorine, and the sum of a, b, c, and d is 1 or 2 in the general formula (1).

10. A compound according to claim 9, wherein A¹, A², A³, and A⁴ each independently represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group in the general formula (1).

13. A liquid crystal composition comprising at least one liquid crystal compound according to any one of claims 3 to 10.

15. A liquid crystal composition according to claim 13, comprising at least one compound represented by general formula (2):

R³—

B¹—

Y¹—

(B²—

Y²)_p—

R⁴ 

 

(2)

(wherein,

R³ and R⁴ each independently represents hydrogen, an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms, in which one CH₂ group or at least two CH₂ groups that are not adjacent to each other may be substituted by oxygen or sulfur, or in which at least one hydrogen may be substitued by fluorine or chlorine,

B¹ and B² each independently represents a trans-1,4-cyclohexylene group (in which one CH₂ group or two CH₂ groups that are not adjacent to each other may be substituted by oxygen or sulfur), a 1,4-phenylene group (in which at least one CH group may be substituted by nitrogen), a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, in which hydrogen may be substituted by —

CN or halogen,

Y¹ and Y² each independently represents —

CH₂CH₂—

, —

CH═

CH—

, —

CH(CH₃)CH₂—

, —

CH₂CH(CH₃)—

, —

CH(CH₃)CH(CH₃)—

, —

CF₂CF₂—

, —

CF═

CF—

, —

CH₂O—

, —

OCH₂—

, —

OCH(CH₃)—

, —

CH(CH₃)O—

, —

(CH₂)₄—

, —

(CH₂)₃O—

, —

O(CH₂)₃—

, —

C≡

C—

, —

CF₂O—

, —

OCF₂—

, —

COO—

, —

OCO, —

COS, —

SCO—

, or a single bond,

when Y² and B² respectively exist in plural, they may be identical to each other or different from each other, and

p represents 0, 1 or

     2).

17. A liquid crystal composition according to claim 13, comprising at least one compound selected from the group consisting of compounds represented by general formula (3a), general formula (3b), and general formula (3c):

18. A liquid crystal composition according to claim 13, wherein a content ratio of the liquid crystal compound according to any one of claims 3 to 10 is 2 to 30% by mass.

19. A liquid crystal composition according to claim 13, wherein the liquid crystal composition has a dielectric anisotropy value of no more than −

0.2.

11. (canceled)

12. (canceled)

14. (canceled)