Octahydro binaphthyl-based chiral compound-containing liquid-crystal composition and optical element

• US 9,458,125 B2
• Filed: 12/12/2013
• Issued: 10/04/2016
• Est. Priority Date: 12/17/2012
• Status: Active Grant

• Current Assignee: JNC Corporation (Chisso Corporation), JNC Petrochemical Corporation (Chisso Corporation)
• Original Assignee: JNC Corporation (Chisso Corporation), JNC Petrochemical Corporation (Chisso Corporation)
• Inventors: Sago, Koki, Yamamoto, Shin-Ichi
• Primary Examiner(s): Visconti, Geraldina
• Application Number:
  US14/649,917
• Publication Number:
  US 20150291548A1
• Time in Patent Office: 1,027 Days
• Field of Search: 252/299.01, 252/299.6, 252/299.62, 428/1.1
• US Class Current: 1/1
• 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 309/04 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 317/10 not condensed with other rings
• CPC Class Codes: C07D 317/12 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
• CPC Class Codes: C07D 319/06 not condensed with other rings
• CPC Class Codes: C07D 321/00 Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 407/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 493/18 Bridged systems
• 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 19/34 containing at least one heterocyclic ring
• CPC Class Codes: C09K 19/542 Macromolecular compounds
• CPC Class Codes: C09K 19/586 Optically active dopants; chiral dopants
• CPC Class Codes: C09K 19/588 Heterocyclic compounds
• CPC Class Codes: C09K 2019/0411 containing a chlorofluoro-benzene, e.g. 2-chloro-3-fluoro-phenylene-1,4-diyl
• CPC Class Codes: C09K 2019/0466 the linking chain being a -CF2O- chain
• CPC Class Codes: C09K 2019/323 containing a binaphthyl
• CPC Class Codes: C09K 2019/325 containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)
• CPC Class Codes: C09K 2019/3422 the heterocyclic ring being a six-membered ring
• CPC Class Codes: C09K 2019/3427 Six-membered ring with 3 or more oxygen atoms
• CPC Class Codes: C09K 2019/343 : the heterocyclic ring being a seven-membered ring
• CPC Class Codes: C09K 2019/3433 : Seven-membered ring with oxygen(s) in fused, bridged or spiro ring systems
• CPC Class Codes: G02F 1/137 : characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
• CPC Class Codes: G02F 1/13793 : Blue phases

Abstract

A liquid-crystal composition is composed of at least one chiral compound represented by general formula (K1) or (K2) and at least one achiral liquid-crystal component:

(wherein, in formulas (K1) and (K2), R^k1 is, for example, alkyl having 1 to 5 carbons, R^k2 is, for example, alkyl having 1 to 20 carbons, ring A^k1 is, for example, 1,4-phenylene, X^k1 is, for example, a single bond, Y^k1 is, for example, —(CH₂)_n—, n is an integer from 0 to 20, Z^k1 is, for example, a single bond, mk1 is, for example, an integer from 2 to 4, and nk1 and nk2 are, for example, an integer from 0 to 2).

Claims

1. A liquid-crystal composition, comprising at least one chiral compound represented by general formula (K1) or (K2) and at least one achiral liquid-crystal component:

6. The liquid-crystal composition according to claim 1, containing at least one compound represented by general formula (1-A) is contained in the achiral liquid-crystal component:

7. The liquid-crystal composition according to claim 6, containing a compound represented by general formula (1-A) in an amount of 50 to 100% by weight in the achiral liquid-crystal component.

8. The liquid-crystal composition according to claim 6, containing a compound represented by general formula (1-A) in an amount of 50 to 100% by weight in the achiral liquid-crystal component, and further containing at least one chiral compound selected from compounds represented by general formulas (K11) to (K15):

9. The liquid-crystal composition according to claim 1, containing at least one compound represented by any one of general formulas (1-A-01) to (1-A-16) in the achiral liquid-crystal component:

10. The liquid-crystal composition according to claim 9, containing at least one compound represented by any one of general formulas (1-A-01) to (1-A-16) in the achiral liquid-crystal component, wherein a content of the compound is 50 to 100% by weight.

11. The liquid-crystal composition according to claim 9, containing at least one compound represented by any one of general formulas (1-A-01) to (1-A-16) in the achiral liquid-crystal component, and further containing at least one compound represented by general formulas (K11) to (K15) in chiral component K:

12. The liquid-crystal composition according to claim 1, wherein a content of the chiral compound is 0.1 to 30% by weight.

13. The liquid-crystal composition according to claim 1, exhibiting a chiral nematic phase of at least 1°

C. or more in the temperature range of 20 to 70°

C., wherein a helical pitch is 700 nanometers or less at least partially in the temperature range.

14. A monomer-liquid-crystal mixture, containing the liquid-crystal composition according to claim 1 and a polymerizable monomer.

15. The monomer-liquid-crystal mixture according to claim 14, exhibiting a chiral nematic phase of at least 1°

C. or more in the temperature range of −

20 to 70°

C., wherein a helical pitch is 700 nanometers or less at least partially in the temperature range.

16. A polymer-liquid-crystal composite material, obtained by polymerizing the monomer-liquid-crystal mixture according to claim 14, and used in an element driven in the optically isotropic liquid-crystal phase.

17. A polymer-liquid-crystal composite material, obtained by polymerizing the monomer-liquid-crystal mixture according to claim 14 in a non-liquid-crystal isotropic phase or an optically isotropic liquid-crystal phase, and is used for an element driven in the optically isotropic liquid-crystal phase.

18. A liquid-crystal device, having an electrode arranged on one side or both sides, a liquid-crystal composition or a polymer-liquid-crystal composite material arranged between substrates, and an electric field applying means for applying an electric field to the liquid-crystal composition or the polymer-liquid-crystal composite material through the electrode, wherein the polymer-liquid-crystal composite material is according to claim 16.

2. A liquid-crystal composition, comprising at least one chiral compound selected from compounds represented by general formulas (K1-1) to (K1-6) and at least one achiral liquid-crystal component:

3. A liquid-crystal composition, comprising at least one chiral compound represented by general formula (K2-1) or (K2-2) and at least one achiral liquid-crystal component:

4. A liquid-crystal composition, comprising at least one chiral compound represented by general formula (K1-1-1), (K1-1-2), (K1-2-1), (K1-2-2), (K1-4-1), (K1-4-2), (K1-5-1) or (K1-5-2) and at least one achiral liquid-crystal component:

5. A liquid-crystal composition, comprising at least one chiral compound represented by general formula (K2-1-1), (K2-1-2), (K2-2-1), (K2-2-2) or (K2-2-3) and at least one achiral liquid-crystal component:

19. A chiral compound represented by general formula (K1-5-1) or (K1-5-2):

20. A chiral compound represented by general formula (K2-1-1), (K2-1-2), (K2-2-1) or (K2-2-3):