Liquid crystal compound having chroman ring, liquid crystal composition comprising the compound and liquid crystal display device comprising the composition
View Patent ↗The present invention relates to a compound having a chroman ring, which has good thermal and optical stability, adequate optical anisotropy, adequate dielectric anisotropy and superior compatibility with other liquid crystal compounds, a liquid crystal composition comprising the compound, and a liquid crystal device comprising the composition. A compound represented by formula (1) below is provided: where R a is hydrogen or C 1 -C 20 alkyl; R b is halogen, —CN, alkyl (at least one hydrogen of which is replaced by halogen), alkenyl (at least one hydrogen of which may be replaced by halogen), or alkoxy (at least one hydrogen of which may be replaced by halogen); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-phenylene, in which any —CH 2 — may be replaced by —O— or —S—, any —CH═ may be replaced by —N═ and any hydrogen may be replaced by halogen, methyl or —CF 3 ; each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond or C 1 -C 4 alkylene; each of h, k, m and n is independently 0, 1 or 2, the sum of h, k, m and n being 1, 2 or 3; and Q is one of the group represented by formulas (q1), (q2) and (q3) below: where X 1 is hydrogen, halogen, methyl, ethyl, methoxy, ethoxy, —CF 3 , —CF 2 H, —CFH 2 , —OCF 3 , —OCF 2 H, or —OCFH 2 ; and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently hydrogen, halogen or methyl.
1. A compound represented by formula (1):
where R a is hydrogen or C 1 -C 20 alkyl (any —CH 2 — of which may be replaced by —O—, —CH═CH— or —C≡C—); R b is halogen, —CN, C 1 -C 20 alkyl (at least one hydrogen of which is replaced by halogen), C 2 -C 20 alkenyl (at least one hydrogen of which may be replaced by halogen), or C 1 -C 20 alkoxy (at least one hydrogen of which may be replaced by halogen); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene, 1,4-cyclohexenylene, or 1,4-phenylene (any —CH 2 — of which may be replaced by —O— or —S—, any —CH═ of which may be replaced by —N═ and any hydrogen of which may be replaced by halogen, methyl or —CF 3 ); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond, or C 1 -C 4 alkylene (any —CH 2 — of which may be replaced by —O—, —S—, —CH═CH—, —CF═CF— or —C≡C— and any hydrogen of C 1 -C 4 alkylene may be replaced by halogen); each of h, k, m and n is independently 0, 1 or 2, the sum of h, k, m and n being 1, 2 or 3; and Q is any one of the groups represented by formulas (q1), (q2) and (q3):
where X 1 is hydrogen or halogen; and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently hydrogen, halogen or methyl.
2. The compound according to claim 1 , wherein Q is the group represented by formula (q1), X 1 is hydrogen and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently hydrogen or fluorine.
3. The compound according to claim 1 , wherein Q is the group represented by formula (q1), X 1 is fluorine and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently hydrogen or fluorine.
4. The compound according to claim 1 , wherein Q is the group represented by formula (q2), X 1 is hydrogen or fluorine and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently hydrogen or fluorine.
5. The compound according to claim 1 , wherein Q is the group represented by formula (q3), X 1 is hydrogen or fluorine and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently hydrogen or fluorine.
6. A compound represented by any one of formulas (1-1) to (1-5):
where R a is hydrogen, C 1 -C 10 alkyl, C 1 -C 10 alkoxy or C 2 -C 10 alkenyl; R b is halogen, —CN, C 1 -C 10 alkyl (at least one hydrogen of which is replaced by halogen), C 2 -C 10 alkenyl (at least one hydrogen of which may be replaced by halogen), or C 1 -C 10 alkoxy (at least one hydrogen of which may be replaced by halogen); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 O— or —OCF 2 —; X 1 is hydrogen or fluorine; and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently hydrogen, halogen or methyl.
7. The compound according to claim 6 , wherein X 1 is fluorine.
8. The compound according to claim 6 , wherein X 1 is fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond or —CH 2 CH 2 —; each of Y 1 , Y 2 , Y 3 and Y 4 is independently hydrogen, fluorine or methyl; and Y 5 is hydrogen.
9. The compound according to claim 6 , wherein X 1 is fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond or —CH 2 CH 2 —; each of Y 1 , Y 2 , Y 3 and Y 4 is hydrogen; and Y 5 is fluorine or chlorine.
10. The compound according to claim 6 , wherein X 1 is fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is a single bond; each of Y 1 , Y 2 , Y 3 and Y 4 is independently hydrogen, fluorine or methyl; and Y 5 is hydrogen.
11. The compound according to claim 6 , wherein X 1 is fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is a single bond; and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is hydrogen.
12. The compound according to claim 6 , wherein X 1 is hydrogen.
13. The compound according to claim 6 , wherein X 1 is hydrogen; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond or —CH 2 CH 2 —; each of Y 1 , Y 2 , Y 3 and Y 4 is independently hydrogen, fluorine or methyl; and Y 5 is hydrogen.
14. The compound according to claim 6 , wherein X 1 is hydrogen; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond or —CH 2 CH 2 —; each of Y 1 , Y 2 , Y 3 and Y 4 is hydrogen; and Y 5 is fluorine or chlorine.
15. The compound according to claim 6 , wherein X 1 is hydrogen; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is a single bond; each of Y 1 , Y 2 , Y 3 and Y 4 is independently hydrogen, fluorine or methyl; and Y 5 is hydrogen.
16. The compound according to claim 6 , wherein X 1 is hydrogen; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2, A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is a single bond; and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is hydrogen.
17. A compound represented by any one of formulas (1-6) to (1-10):
where R a is hydrogen, C 1 -C 10 alkyl, C 1 -C 10 alkoxy or C 2 -C 10 alkenyl; R b is halogen, —CN, C 1 -C 10 alkyl (at least one hydrogen of which is replaced by halogen), C 1 -C 10 alkoxy (at least one hydrogen of which may be replaced by halogen), or C 2 -C 10 alkenyl (at least one hydrogen of which may be replaced by halogen); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 O— or —OCF 2 —; X 1 is hydrogen or fluorine; and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently hydrogen, halogen or methyl.
18. The compound according to claim 17 , wherein X 1 is hydrogen or fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond or —CH 2 CH 2 —; each of Y 1 , Y 2 , Y 3 and Y 4 is independently hydrogen, fluorine or methyl; and Y 5 is hydrogen.
19. The compound according to claim 17 , wherein X 1 is hydrogen or fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond or —CH 2 CH 2 —; each of Y 1 , Y 2 , Y 3 and Y 4 is hydrogen; and Y 5 is fluorine or chlorine.
20. The compound according to claim 17 , wherein X 1 is hydrogen or fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is a single bond; each of Y 1 , Y 2 , Y 3 and Y 4 is independently hydrogen, fluorine or methyl; and Y 5 is hydrogen.
21. The compound according to claim 17 , wherein X 1 is hydrogen or fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is a single bond; and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is hydrogen.
22. A compound represented by any one of formulas (1-11) to (1-15):
where R a is hydrogen, C 1 -C 10 alkyl, C 1 -C 10 alkoxy or C 2 -C 10 alkenyl; R b is halogen, —CN, C 1 -C 10 alkyl (at least one hydrogen of which is replaced by halogen), C 1 -C 10 alkoxy (at least one hydrogen of which may be replaced by halogen), or C 2 -C 10 alkenyl (at least one hydrogen of which may be replaced by halogen); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 O— or —OCF 2 —; X 1 is hydrogen or fluorine; and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is independently hydrogen, halogen or methyl.
23. The compound according to claim 22 , wherein X 1 is hydrogen or fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond or —CH 2 CH 2 —; each of Y 1 , Y 2 , Y 3 and Y 4 is independently hydrogen, fluorine or methyl; and Y 5 is hydrogen.
24. The compound according to claim 22 , wherein X 1 is hydrogen or fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is independently a single bond or —CH 2 CH 2 —; each of Y 1 , Y 2 , Y 3 and Y 4 is hydrogen; and Y 5 is fluorine or chlorine.
25. The compound according to claim 22 , wherein X 1 is hydrogen or fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is a single bond; each of Y 1 , Y 2 , Y 3 and Y 4 is independently hydrogen, fluorine or methyl; and Y 5 is hydrogen.
26. The compound according to claim 22 , wherein X 1 is hydrogen or fluorine; R a is hydrogen, C 1 -C 7 alkyl or C 2 -C 7 alkenyl; R b is halogen, —CN, —OCF 3 , —OCF 2 H, or C 1 -C 7 alkyl (at least one hydrogen of which is replaced by fluorine); each of A 1 , A 2 , A 3 and A 4 is independently 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 1 , Z 2 , Z 3 and Z 4 is a single bond; and each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is hydrogen.
27. A liquid crystal composition which comprises at least two compounds, at least one of which is a compound of claim 1 and at least one of which may be an optically active compound.
28. A liquid crystal composition which comprises at least one compound of claim 1 and at least one compound selected from the group consisting of the compounds represented by formulas (2), (3) and (4), and may comprise at least one optically active compound:
where R 1 is C 1 -C 10 alkyl (any —CH 2 — of which may be replaced by —O— or —CH═CH— and any hydrogen of which may be replaced by fluorine); X 2 is fluorine, chlorine, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 , or —OCF 2 CHFCF 3 ; each of ring B and ring D is independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); ring E is 1,4-cyclohexylene or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); each of Z 5 and Z 6 is independently —(CH 2 ) 2 —, —(CH 2 ) 4 —, —COO—, —CF 2 O—, —OCF 2 —, —CH═CH— or a single bond; and each of L 1 and L 2 is independently hydrogen or fluorine.
29. A liquid crystal composition which comprises at least one compound of claim 1 and at least one compound selected from the group consisting of the compounds represented by formulas (5) and (6), and may comprise at least one optically active compound:
where each of R 2 and R 3 is independently C 1 -C 10 alkyl (any —CH 2 — of which may be replaced by —O— or —CH═CH— and any hydrogen of which may be replaced by fluorine); X 3 is —CN or —C≡C—CN; ring G is 1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; ring J is 1,4-cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); ring K is 1,4-cyclohexylene or 1,4-phenylene; Z 7 is —(CH 2 ) 2 —, —COO—, —CF 2 O—, —OCF 2 — or a single bond; each of L 3 , L 4 and L 5 is independently hydrogen or fluorine; and each of b, c and d is independently 0 or 1.
30. A liquid crystal composition which comprises at least one compound of claim 1 and at least one compound selected from the group consisting of the compounds represented by formulas (7) to (9), and may comprise at least one optically active compound:
where each of R 4 and R 5 is independently C 1 -C 10 alkyl (any —CH 2 — of which may be replaced by —O— or —CH═CH— and any hydrogen of which may be replaced by fluorine); each of ring M, ring P and ring Q is independently 1,4-cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); and each of Z 7 and Z 8 is independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond.
31. The composition according to claim 28 , which further comprises at least one compound selected from the group consisting of the compounds represented by formulas (5) and (6):
where each of R 2 and R 3 is independently C 1 -C 10 alkyl (any —CH 2 — of which may be replaced by —O— or —CH═CH— and any hydrogen of which may be replaced by fluorine); X 3 is —CN or —C≡C—CN; ring G is 1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; ring J is 1,4-cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); ring K is 1,4-cyclohexylene or 1,4-phenylene; Z 7 is —(CH 2 ) 2 —, —COO—, —CF 2 O—, —OCF 2 — or a single bond; each of L 3 , L 4 and L 5 is independently hydrogen or fluorine; and each of b, c and d is independently 0 or 1.
32. The composition according to claim 28 , which further comprises at least one compound selected from the group consisting of the compounds represented by formulas (7), (8) and (9):
where each of R 4 and R 5 is independently C 1 -C 10 alkyl (any —CH 2 — of which may be replaced by —O— or —CH═CH— and any hydrogen of which may be replaced by fluorine); each of ring M, ring P and ring Q is independently 1,4-cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); and each of Z 7 and Z 8 is independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond.
33. The composition according to claim 29 , which further comprises at least one compound selected from the group consisting of the compounds represented by formulas (7), (8) and (9):
where each of R 4 and R 5 is independently C 1 -C 10 alkyl (any —CH 2 — of which may be replaced by —O— or —CH═CH— and any hydrogen of which may be replaced by fluorine); each of ring M, ring P and ring Q is independently 1,4-cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene (any hydrogen of which may be replaced by fluorine); and each of Z 7 and Z 8 is independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH— or a single bond.
34. A liquid crystal device comprising the liquid crystal composition of claim 27 .
35. A liquid crystal device comprising the liquid crystal composition of claim 28 .
36. A liquid crystal device comprising the liquid crystal composition of claim 29 .
37. A liquid crystal device comprising the liquid crystal composition of claim 30 .
38. A liquid crystal device comprising the liquid crystal composition of claim 31 .
39. A liquid crystal device comprising the liquid crystal composition of claim 32 .
40. A liquid crystal device comprising the liquid crystal composition of claim 33 .