2,2′-binaphthalene ester chiral dopants for cholesteric liquid crystal displays
View Patent ↗A liquid crystal composition comprising a chiral dopant compound represented by the following structure (Structure 1): wherein: R1 and R2 are independently hydrogen, —(C═O)R9, —(C═O)R10, alkyl, aryl, alkaryl, alkenyl, cycloalkyl, alkoxyaryl, or heterocyclic all either substituted or unsubstituted, or combine to form a carbocyclic or heterocyclic ring; and R3-R9 are as described in the disclosure. Also featured are liquid crystal compositions comprising a chiral dopant compound represented by any of Structure 2-4 as described in the disclosure.
1. A liquid crystal composition comprising a chiral dopant compound represented by the following structure:
wherein:
R 1 and R 2 are independently hydrogen, —(C═O)R 9 , —(C═O)R 10 , alkyl, aryl, alkaryl, alkenyl, cycloalkyl, alkoxyaryl, or heterocyclic all either substituted or unsubstituted, or combine to form a carbocyclic ring;
R 3 is hydrogen, halogen, cyano, alkoxy, NHCOR 9 , NHSO 9 R 9 , COOR 9 , OCOR 9 , aryl, alkyl, alkenyl, cycloalkyl, or heterocyclic all either substituted or unsubstituted;
R 4 is hydrogen, alkyl, aryl, alkenyl, cycloalkyl, or heterocyclic all either substituted or unsubstituted;
R 5 , R 6 , R 7 , and R 8 are independently hydrogen, halogen, cyano, alkoxy, NHCOR 9 , NHSO 2 R 9 , COOR 9 , OCOR 9 , aryl, alkyl, alkenyl, cycloalkyl, alkoxyaryl or heterocyclic all either substituted or unsubstituted, or combine with each other, or R 5 can combine with R 4 , to form a carbocyclic or heterocyclic ring;
R 9 and R 10 are independently alkyl, alkoxy, aryl, naphthyl, styryl, alkenyl, cycloalkyl, alkoxyaryl, cycloalkoxy, or heterocyclic all either substituted or unsubstituted, or combine to form a carbocyclic ring.
2. A liquid crystal composition of claim 1 comprising an enantiomerically excess of one enantiomer of said chiral dopant compound.
3. A liquid crystal composition of claim 1 wherein R 9 and R 10 are aryl either substituted or unsubstituted as defined by: —R 9 or —R 10 =—(Y—K) p —Z: wherein K is a single bond or double bond or bivalent linking selected from the group consisting of: —C(═O)O—; —O(C═O)—; —CH 2 CH 2 —; —CH═CH—; —C≡C—; —OCH 2 —; —CH 2 O—; —N═CH—; —CH═N—; —O(C═O)O—; —C≡C—C≡C—; —COCH═CH—; —CH═CHCO—; —O—; —S—; and SO 2 ; as long as oxygen atoms are not linked directly to one another; wherein Y and Z independently are optionally selected from the group consisting of: 1,4-phenylene in which, in addition, one or more methylene may be replaced by —N═; 1,4-cyclohexyl in which, in addition, one or more non-adjacent methylene units may be replaced by O or S; 1,4-cyclohexylene; 1,4-bicyclo[2.2.2]octylene; piperidine-1,4-diyl; decahydronaphthalene-1,6-diyl; and 1,2,3,4-tetrahydronaphthalene-1,6-diyl; wherein each of the Y or Z groups may be unsubstituted or mono-substituted or poly-substituted with halogen, cyano, isocyanato, or nitro groups, or alkyl, alkoxyl, or alkanoyl groups bearing 1-12 carbons where one or more hydrogens may be replaced with chlorine or fluorine; and wherein p=0, 1, 2, 3, 4.
4. A liquid crystal composition of claim 1 wherein R 3 is an aryl group either substituted or unsubstituted.
5. A liquid crystal composition of claim 1 comprising said chiral dopant admixed with a liquid crystal material, wherein said chiral dopant compound is optionally in a polymerized form.
6. A liquid crystal composition of claim 5 further comprising a polymer binder in which domains of the liquid crystal material are dispersed.
7. A liquid crystal composition of claim 5 further comprising at least one of a catalyst, a sensitizer, a stabilizer, a co-reacting monomer, or a surface-active compound.
8. A liquid crystalline composition of claim 5 wherein the liquid crystalline composition is STN, TN, chiral nematic, or ferroelectric.
9. A liquid crystalline composition of claim 5 which is chiral nematic.
10. A liquid crystal display, electronic writer/tablet, electronic skin, optical element, or color filter comprising the liquid crystal composition of claim 5 .
11. A liquid crystal display, electronic writer/tablet, electronic skin, optical element, or color filter comprising the liquid crystal composition of claim 6 .
12. A liquid crystal display, electronic writer/tablet, electronic skin, optical element, or color filter comprising the liquid crystal composition of claim 7 .
13. The display of claim 10 wherein the display is selected from the group consisting of a STN, TN, TFT-TN, guest-host, phase change, polymer free cholesteric texture, polymer stabilized cholesteric texture and ferroelectric display.
14. A liquid crystal composition comprising a chiral dopant compound represented by the following structure:
wherein:
R 3 is hydrogen, halogen, cyano, alkoxy, NHCOR 9 , NHSO 2 R 9 , COOR 9 , OCOR 9 , aryl, alkyl, alkenyl, cycloalkyl, or heterocyclic all either substituted or unsubstituted;
R 4 is hydrogen, alkyl, aryl, alkenyl, cycloalkyl, or heterocyclic all either substituted or unsubstituted;
R 5 , R 6 , R 7 , and R 8 are independently hydrogen, halogen, cyano, alkoxy, NHCOR 9 , NHSO 2 R 9 , COOR 9 , OCOR 9 , aryl, alkyl, alkenyl, cycloalkyl, alkoxyaryl or heterocyclic all either substituted or unsubstituted, or combine with each other, or R 5 can combine with R 4 , to form a carbocyclic or heterocyclic ring;
R 9 is independently alkyl, aryl, alkenyl, cycloalkyl, alkoxyaryl or heterocyclic all either substituted or unsubstituted;
R 11 and R 12 are independently alkyl, alkoxy, aryl, naphthyl, styryl, alkenyl, cycloalkyl, cycloalkyloxy, alkoxyaryl or heterocyclic all either substituted or unsubstituted, or combine to form a carbocyclic or heterocyclic ring.
15. A liquid crystal composition of claim 14 comprising an enantiomerically excess of one enantiomer of said chiral dopant compound.
16. A liquid crystal composition of claim 14 wherein R 11 and R 12 are aryl either substituted or unsubstituted as defined by: —R 11 or —R 12 =—(Y—K) p —Z: wherein K is a single bond or double bond or bivalent linking selected from the group consisting of: —C(═O)O—; —O(C═O)—; —CH 2 CH 2 —; —CH═CH—; —C≡C—; —OCH 2 —; —CH 2 O—; —N═CH—; —CH═N—; —O(C═O)O—; —C≡C—C≡C—; —COCH═CH—; —CH═CHCO—; —O—; —S—; and SO 2 ; as long as oxygen atoms are not linked directly to one another; wherein Y and Z independently are optionally selected from the group consisting of: 1,4-phenylene in which, in addition, one or more methylene may be replaced by —N═; 1,4-cyclohexyl in which, in addition, one or more non-adjacent methylene units may be replaced by O or S; 1,4-cyclohexylene; 1,4-bicyclo[2.2.2]octylene; piperidine-1,4-diyl; decahydronaphthalene-1,6-diyl; and 1,2,3,4-tetrahydronaphthalene-1,6-diyl; wherein each of the Y or Z groups may be unsubstituted or mono-substituted or poly-substituted with halogen, cyano, isocyanato, or nitro groups, or alkyl, alkoxyl, or alkanoyl groups bearing 1-12 carbons where one or more hydrogens may be replaced with chlorine or fluorine; and wherein p=0, 1, 2, 3, 4.
17. A liquid crystal composition of claim 14 wherein R 3 is an aryl group either substituted or unsubstituted.
18. A liquid crystal composition of claim 14 comprising said chiral dopant admixed with a liquid crystal material, wherein said chiral dopant compound is optionally in a polymerized form.
19. A liquid crystal composition of claim 18 further comprising a polymer binder in which domains of the liquid crystal material are dispersed.
20. A liquid crystal composition of claim 18 further comprising at least one of a catalyst, a sensitizer, a stabilizer, a co-reacting monomer, or a surface-active compound.
21. A liquid crystalline composition of claim 18 wherein the liquid crystalline composition is STN, TN, chiral nematic, or ferroelectric.
22. A liquid crystalline composition of claim 18 which is chiral nematic.
23. A liquid crystal display, electronic writer/tablet, electronic skin, optical element, or color filter comprising the liquid crystal composition of claim 18 .
24. The display of claim 23 wherein the display is selected from the group consisting of a STN, TN, TFT-TN, guest-host, phase change, polymer free cholesteric texture, polymer stabilized cholesteric texture and ferroelectric display.
25. A liquid crystal composition of claim 1 , wherein: R 1 and R 2 are —(C═O)R 9 and —(C═O)R 10 , respectively.
26. A liquid crystal composition of claim 25 comprising an enantiomerically excess of one enantiomer of said chiral dopant compound.
27. A liquid crystal composition of claim 25 wherein R 9 and R 10 are aryl either substituted or unsubstituted as defined by: —R 9 or —R 10 =—(Y—K) p —Z: wherein K is a single bond or double bond or bivalent linking selected from the group consisting of: —C(═O)O—; —O(C═O)—; —CH 2 CH 2 —; —CH═CH—; —C≡C—; —OCH 2 —; —CH 2 O—; —N═CH—; —CH═N—; —O(C═O)O—; —C≡C—C≡C—; —COCH═CH—; —CH═CHCO—; —O—; —S—; and SO 2 ; as long as oxygen atoms are not linked directly to one another; wherein Y and Z independently are optionally selected from the group consisting of: 1,4-phenylene in which, in addition, one or more methylene may be replaced by —N═; 1,4-cyclohexyl in which, in addition, one or more non-adjacent methylene units may be replaced by O or S; 1,4-cyclohexylene; 1,4-bicyclo[2.2.2]octylene; piperidine-1,4-diyl; decahydronaphthalene-1,6-diyl; and 1,2,3,4-tetrahydronaphthalene-1,6-diyl; wherein each of the Y or Z groups may be unsubstituted or mono-substituted or poly-substituted with halogen, cyano, isocyanato, or nitro groups, or alkyl, alkoxyl, or alkanoyl groups bearing 1-12 carbons where one or more hydrogens may be replaced with chlorine or fluorine; and wherein p=0, 1, 2, 3, 4.
28. A liquid crystal composition of claim 25 wherein R 3 is an aryl group either substituted or unsubstituted.
29. A liquid crystal composition of claim 25 comprising said chiral dopant admixed with a liquid crystal material, wherein said chiral dopant compound is optionally in a polymerized form.
30. A liquid crystal composition of claim 29 further comprising a polymer binder in which domains of the liquid crystal material are dispersed.
31. A liquid crystal composition of claim 29 further comprising at least one of a catalyst, a sensitizer, a stabilizer, a co-reacting monomer, or a surface-active compound.
32. A liquid crystalline composition of claim 29 wherein the liquid crystalline composition is STN, TN, chiral nematic, or ferroelectric.
33. A liquid crystalline composition of claim 29 which is chiral nematic.
34. A liquid crystal display, electronic writer/tablet, electronic skin, optical element, or color filter comprising the liquid crystal composition of claim 29 .
35. The display of claim 34 wherein the display is selected from the group consisting of a STN, TN, TFT-TN, guest-host, phase change, polymer free cholesteric texture, polymer stabilized cholesteric texture and ferroelectric display.