Photochemically active chiral compounds and compositions containing the same
The present invention relates to a phototunable chiral dopant represented by the following structure: wherein: A, B, C and D are independent divalent groups; X and Z are any independently selected substituent; n is an integer and independently varies from 0 to 3; q is an integer and independently varies from 0 to 5; RNG1 and RNG2 independently represent any ring group; m represents an integer independently varying from 0 to 4; p represents an integer independently varying from 1 to 4; Q independently represents a carbon C—R C , or nitrogen, wherein R C is independently hydrogen or any substituent. The invention also relates to the use of the dopant in a liquid crystalline composition and a display containing the same, as well as a material composition comprising an enantiomeric excess of one enantiomer of the compound.
1. A material composition comprising an enantiomeric excess of one enantiomer of a compound
wherein:
A and C are the same and selected from one of CH 2 , —O—, and —C(R1)(R2)-;
B and D are the same, but independent of A and C, and are selected from one of CH 2 , —O—, and C(R1)(R2);
wherein R1 and R2 are independently selected from a C 1 -C 5 alkyl group and C 1 -C 5
alkoxy group and optionally wherein if R1 and R2 groups are on the same ring, they can form a fused ring;
X is each independently selected from one of one or more H atoms and a halogen;
Z is selected from one of an H atom, halogen, CN, straight, chain, branched alkyl, alkoxyl, and nitrogen based substituent groups;
RNG1 and RNG2 are each independently selected from one of 1,4-phenylene in which, one or more CH groups may be replaced by N, 1,4-cyclohexylene in which, one or two non-adjacent CH2 groups may be replaced by O and/or S, 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and mono- or poly-substituted derivatives of such compounds substituted with halogen, cyano or nitro groups, or alkyl, alkoxy or alkanoyl groups having 1 to 12 C atoms wherein one or more H atoms may be substituted by an F or Cl;
n represents an integer independently varying from 0 to 3;
m represents an integer independently varying from 0 to 2;
p represents an integer independently varying from 1 to 4;
q represents an integer independently varying from 0 to 5; and
Q each independently represents a carbon C—Rc, or nitrogen, wherein Rc is independently hydrogen or any substituent.
2. The material of claim 1 wherein A and B comprise a first five membered ring, and C and D comprise a second five membered ring, wherein said first ring and said second ring share a spirocarbon atom to which A and C are attached.
3. The material of claim 1 wherein A, B, C and D are independently methylene or di-substituted carbon (C(R1(R2)).
4. The material of claim 1 wherein A, B, C and D are methylene (—CH 2 —).
5. The material of claim 1 wherein Z is an alkoxy (C1-C8) or a nitrogen based substituent group.
6. The material of claim 1 wherein Z is an alkoxy (C1-C8).
7. The material of claim 1 wherein X is hydrogen.
8. The material of claim 1 wherein n is 0.
9. The material of claim 1 wherein q is 1.
10. The material of claim 1 wherein m is independently 0 or 1.
11. The material of claim 1 wherein p is 1.
12. The material of claim 1 wherein the stereochemistry of(-Q═Q-) independently is trans (E) or cis (Z).
13. The material of claim 1 wherein the stereochemistry of(-Q═Q-) is trans.
14. The material of claim 1 wherein Q is C—R c .
15. The material of claim 14 wherein R c is hydrogen.
16. The material of claim 1 represented by Structure 2:
17. The material of claim 16 wherein R c is hydrogen.
18. The material of claim 16 wherein the stereochemistry of (R c C═CR c ) independently is trans or cis.
19. The material of claim 18 wherein R c C═CR c is trans.
20. The material of claim 16 wherein Z is an alkoxy (C1-C8) or a nitrogen based substituent group.
21. The material of claim 16 wherein Z is an alkoxy (C1-C8).
22. The material of claim 16 wherein q is 1.
23. The material of claim 16 wherein RNG1 and RGN2 are 1,4-phenylene.
24. The material of claim 16 wherein m is independently 0 or 1.
25. The material of claim 16 wherein p is 1.
26. The material of claim 16 wherein X is hydrogen.
27. The material of claim 16 wherein n is 1.
28. The material of claim 1 represented by Structure 3:
29. The material of claim 28 wherein R c is hydrogen.
30. The material of claim 28 wherein X is hydrogen.
31. The material of claim 28 wherein Z is an alkoxy (C1-C8) or a nitrogen based substituent group.
32. The material of claim 28 wherein Z is an alkoxy (C1-C8).