High polarization ferroelectric liquid crystal compositions

• US 7,195,719 B1
• Filed: 01/03/2002
• Issued: 03/27/2007
• Est. Priority Date: 01/03/2001
• Status: Expired due to Fees

• Current Assignee: Citizen Finetech Miyota Company Limited (Citizen Electronics Company Limited)
• Original Assignee: Displaytech Inc (Micron Technology, Inc.)
• Inventors: Wand, Michael, Thurmes, William N., Chen, Xin Hua
• Primary Examiner(s): WU, SHEAN CHIU
• Application Number:
  US10/038,054
• Time in Patent Office: 1,909 Days
• Field of Search: 428/1.1, 252/299.61, 252/299.5, 252/299.63, 252/299.64, 252/299.66, 252/299.67, 544/298, 544/334, 544/242, 544/335, 549/324, 549/455, 549/563
• US Class Current: 252/299.61
• CPC Class Codes: C07D 239/26 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C09K 19/0225 Ferroelectric
• CPC Class Codes: C09K 19/3458 Uncondensed pyrimidines
• CPC Class Codes: C09K 19/3469 Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-
• CPC Class Codes: C09K 19/586 Optically active dopants; chiral dopants
• CPC Class Codes: C09K 19/588 Heterocyclic compounds

Abstract

The invention relates to chiral nonracemic liquid crystal compounds having achiral tails comprising a perfluoroalkyl terminal portion which are useful as components in liquid crystal to impart high polarization to the mixture. The materials of this invention can be combined with known liquid crystal host materials to impart improved properties. Chiral nonracemic compounds of this invention can function as additives or dopants in host materials to impart chirality into an LC material.

Claims

1. A chiral, non-racemic liquid crystal composition comprising a chiral compound of the formula:

C_nF_2n+1C_mH_2m—

Y—

R^T-[A]_a-[R^A]_p-[B]_b—

[R^B]_q—

XCR

wherein

n is an integer from 1 to 20;

m is an integer from 2 to 20;

a, b, p and q are either 0 or 1, when p is 0, a is 0 and when q is 0, b is 0;

Y is a single bond or oxygen;

X is selected from the group consisting of a single bond, oxygen, —

CO—

, —

O—

CO—

, —

CO—

O— and

a lower alkylene group where one or more carbon atoms is optionally substituted with one or more of oxygen or —

CO—

;

CR is selected from the group consisting of;

2. The composition of claim 1 wherein CR is selected from the group consisting:

3. The composition of claim 1 wherein each of R^T, R^A, and R^B is independently selected from the group consisting of naphthylene, phenylene, cyclohexylene, cyclohexenylene, pyrimidinylene, pyridinylene, 1,2,34-tetrahydronaphthylene, and 1,4-dihydronaphthylene.

4. The composition of claim 1, wherein said mesogenic core is a biaryl moiety.

5. The composition of claim 1 wherein said mesogenic core selected from the group consisting of:

6. The composition of claim 1, wherein said chiral, non-racemic liquid crystal composition further comprises an achiral liquid crystal host.

7. The composition of claim 6, wherein the said achiral liquid crystal host comprises an achiral compound selected from the group consisting of:

8. The composition of claim 1 wherein n=m.

9. The composition of claim 1 wherein Y is O.

10. The composition of claim 1 wherein the total amount of chiral compound in said chiral, non-racemic liquid crystal composition is 10% or less.

11. The composition of claim 1 which has Ps of 10 nC/cm² or more at room temperature.

12. The composition of claim 11 wherein the total amount of chiral compound in said chiral, non-racemic liquid crystal composition is 5% by weight or less.

13. A compound having the formula:

15. A chiral, non-racemic liquid crystal composition which comprises one or more chiral compounds of claim 13.

14. A chiral, non-racemic liquid crystal composition comprising a chiral compound of the formula:

C_nF_2n+1C_mH_2m—

Y—

R^T—

[A]_a—

[R^A]_p—

[B]_b—

[R^B]_q—

XCR

wherein

n is an integer from 1 to 20;

m is an integer from 2 to 20;

a, b, p and q are either 0 or 1, when p is 0, a is 0 and when q is 0, b is 0;

Y is a singe bond or an oxygen;

X is selected from the group consisting of a single bond, oxygen, —

CO—

, —

O—

CO—

, —

CO—

O— and

a lower alkyl group where one or more carbon atoms is optionally substituted with one or more of oxygen or —

CO—

;

CR is selected from the group consisting of;

17. The chiral, non-racemic liquid crystal composition of claim 14, wherein the chiral compound is the formula:

16. A compound of the formula:

18. A non-racemic liquid crystal composition comprising a rod-like chiral liquid crystal compound and optionally an achiral liquid crystal host, wherein said rod-like chiral liquid crystal compound comprises a mesogenic core moiety having an achiral fluorinated alkyl tail on one end of the long axis of said mesogenic core moiety and a chiral tail on the other end of the long axis of said mesogenic core moiety, wherein:

said mesogenic core comprises a cyclic ring system, wherein said cyclic ring system is selected from the group consisting of cycloalkylene, cycloalkenylene, heterocycloalkylene, heterocycloalkenylene, arylene, heteroarylene, and a combination of two or more thereof; and

said chiral tail comprises a chiral moiety selected from the group consisting of;

19. The non-racemic liquid crystal composition of claim 18, wherein said mesogenic core moiety comprises three cyclic ring systems or less.

20. The non-racemic liquid crystal composition of claim 19, wherein each of said cyclic ring system is selected from the group consisting of cyclohexylene, cyclohexenylene, heterocycloalkylene comprising one or two ring nitrogen atoms, heterocycloalkenylene comprising one or two ring nitrogen atoms, phenylene, naphthylene, an heteroarylene comprising one or two ring nitrogen atoms.

21. The non-racemic liquid crystal composition of claim 18, wherein each of said cyclic ring system is independently a six-membered monocyclic ring system or a ten-membered bicyclic ring system.

22. A rod-like liquid crystal compound comprising mesogenic core moiety, wherein said mesogenic core moiety is substituted with an achiral fluorinated alkyl substituent on one end of the long axis of said mesogenic core moiety and a chiral substituent on the other end of the long axis of said mesogenic core moiety, wherein:

said mesogenic core comprises a cyclic ring system, wherein said cyclic ring system is selected from the group consisting of cycloalkylene, cycloalkenylene, heterocycloalkylene, heterocycloalkenylene, arylene, heteroarylene, and a combination of two or more thereof, and

said chiral substituent comprises a chiral moiety selected from the group consisting of;