Liquid crystal compound, liquid crystal composition and, liquid crystal display device

1. A compound represented by formula (1):

wherein R is hydrogen, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons, or alkenyloxy having 2 to 11 carbons;

ring A 1 , ring A 2 , and ring A 3 are each independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and in these rings, hydrogen may be replaced by halogen;

Z 1 , Z 2 , and Z 3 are each independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CF═CF—, —(CH 2 ) 4 —, —(CH 2 ) 2 CF 2 O—, —OCF 2 (CH 2 ) 2 —, —CH═CH(CH 2 ) 2 —, or —(CH 2 ) 2 CH═CH—;

L 1 and L 2 are each independently hydrogen or halogen, and at least one of L 1 and L 2 is halogen;

W is —CH═CH— or —C≡C—, wherein both L 1 and L 2 are halogen when W is —CH═CH—; and

n and m are each independently an integer of 0 to 2, and the sum of n and m is an integer of 0 to 3.

2. The compound according to claim 1 , wherein ring A 1 , ring A 2 , and ring A 3 are each independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene in which arbitrary hydrogen is replaced by fluorine.

3. The compound according to claim 2 , wherein Z 1 , Z 2 , and Z 3 are each independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, or —CF═CF—.

4. A compound represented by formula (1-1):

wherein R is hydrogen, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkoxy having 1 to 11 carbons;

ring A 1 , ring A 2 , and ring A 3 are each independently, 1,4-cyclohexylene, 1,4-phenylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene in which arbitrary hydrogen is replaced by fluorine;

Z 1 , Z 2 , and Z 3 are each independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, or —CF═CF—;

W is —CH═CH— or —C≡C—;

L 1 is hydrogen, fluorine, or chlorine; and

n and m are each independently an integer of 0 to 2, and the sum of n and m is an integer of 0 to 3.

5. The compound according to claim 4 , wherein ring A 1 , ring A 2 , and ring A 3 are each independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which arbitrary hydrogen is replaced by fluorine.

6. The compound according to claim 4 , wherein at least one of ring A 1 , ring A 2 , and ring A 3 is 1,3-dioxane-2,5-diyl.

7. The compound according to claim 4 , wherein at least one of ring A 1 , ring A 2 , and ring A 3 is tetrahydropyran-2,5-diyl.

8. The compound according to claim 4 , wherein at least one of ring A 1 , ring A 2 , and ring A 3 is pyrimidine-2,5-diyl.

9. The compound according to claim 5 , wherein Z 1 , Z 2 , and Z 3 are each independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —CF 2 O—, or —CH 2 O—.

10. The compound according to claim 5 , wherein Z 1 , Z 2 , and Z 3 are a single bond.

11. A compound represented by any one of formulas (1-2) to (1-10):

wherein Ra is independently hydrogen, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkoxy having 1 to 11 carbons;

Z 1 , Z 2 , and Z 3 are each independently a single bond, —CH 2 CH 2 —, —CH═CH—, —COO—, or —CF 2 O—;

X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are each independently hydrogen or fluorine; and

W is independently —CH═CH— or —C≡C—.

12. The compound according to claim 11 , wherein Z 1 , Z 2 , and Z 3 are a single bond in formulas (1-2) to (1-10).

13. The compound according to claim 12 , wherein X 1 is fluorine, and X 2 , X 3 , X 4 , X 5 , and X 6 are hydrogen in formulas (1-2) to (1-10).

14. The compound according to claim 12 , wherein X 1 and X 2 are fluorine, and X 3 , X 4 , X 5 , and X 6 are hydrogen in formulas (1-2) to (1-10).

15. The compound according to claim 12 , wherein X 1 and X 3 are fluorine, and X 2 , X 4 , X 5 , and X 6 are hydrogen in formulas (1-2) to (1-10).

16. The compound according to claim 12 , wherein X 1 , X 2 , and X 3 are fluorine, and X 4 , X 5 , and X 6 are hydrogen in formulas (1-2) to (1-10).

17. The compound according to claim 12 , wherein W is —CH═CH— in formulas (1-2) to (1-10).

18. A liquid crystal composition comprising at least one compound according to claim 4 .

19. The liquid crystal composition according to claim 18 , further comprising at least one compound selected from the group of compounds each represented by formulas (2), (3), and (4):

wherein R 1 is independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH2- may be replaced by —O—;

M 1 is independently fluorine, chlorine, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 , or —OCF 2 CHFCF 3 ;

ring B 1 , ring B 2 , and ring B 3 are each independently 1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, tetrahydropyran-2,5-diyl, or 1,4-phenylene in which arbitrary hydrogen is replaced by fluorine;

Z 4 and Z 5 are each independently —(CH 2 ) 2 —, —(CH 2 ) 4 —, —COO—, —CF 2 O—, —OCF 2 —, —CH═CH—, or a single bond; and

L 3 and L 4 are each independently hydrogen or fluorine.

20. The liquid crystal composition according to claim 18 , further comprising at least one compound selected from the group of compounds represented by formula (5):

wherein R 2 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH 2 — may be replaced by —O—;

M 2 is —C≡N or —C≡C—C≡N;

ring C 1 , ring C 2 , and ring C 3 are each independently 1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, tetrahydropyran-2,5-diyl, or 1,4-phenylene in which arbitrary hydrogen is replaced by fluorine;

Z 6 is —(CH 2 ) 2 —, —COO—, —CF 2 O—, —OCF 2 —, —C≡C—, —CH 2 O—, or a single bond;

L 5 and L 6 are each independently hydrogen or fluorine; and

q is an integer of 0 to 2 and r is 0 or 1.

21. The liquid crystal composition according to claim 18 , further comprising at least one compound selected from the group of compounds each represented by formulas (6), (7), (8), (9), and (10):

wherein R 3 and R 4 are each independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH 2 — may be replaced by —O—;

ring D 1 and ring D 2 are each independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, decahydronaphthalene-2,6-diyl, or 1,4-phenylene in which arbitrary hydrogen is replaced by fluorine;

Z 7 and Z 8 are each independently —(CH 2 ) 2 —, —COO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —(CH 2 ) 2 CF 2 O—, —OCF 2 (CH 2 ) 2 —, or a single bond; and

L 8 and L 9 are each independently chlorine or fluorine.

22. The liquid crystal composition according to claim 18 , further comprising at least one compound selected from the group of compounds each represented by formulas (11), (12), and (13):

wherein R 5 and R 6 are each independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH 2 — may be replaced by —O—;

ring E 1 , ring E 2 , and ring E 3 are each independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene; and

Z 9 and Z 10 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH—, or a single bond, and Z 11 is —COO— or a single bond.

23. The liquid crystal composition according to claim 20 , further comprising at least one compound selected from the group of compounds each represented by formulas (11), (12), and (13):

wherein R 5 and R 6 are each independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH 2 — may be replaced by —O—;

ring E 1 , ring E 2 , and ring E 3 are each independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene; and

Z 9 and Z 10 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH—, or a single bond, and Z 11 is —COO— or a single bond.

24. The liquid crystal composition according to claim 21 , further comprising at least one compound selected from the group of compounds each represented by formulas (11), (12), and (13):

wherein R 5 and R 6 are each independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH 2 — may be replaced by —O—;

ring E 1 , ring E 2 , and ring E 3 are each independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene; and

Z 9 and Z 10 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH—, or a single bond, and Z 11 is —COO— or a single bond.

25. The liquid crystal composition according to claim 18 , further comprising at least one optically active compound.

26. The liquid crystal composition according to claim 18 , further comprising at least one antioxidant and/or ultraviolet absorber.

27. A liquid crystal display element comprising the liquid crystal composition according to claim 18 .

28. The liquid crystal composition according to claim 19 , further comprising at least one compound selected from the group of compounds represented by formula (5):

wherein R 2 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH 2 — may be replaced by —O—;

M 2 is —C≡N or —C≡C—C≡N;

ring C 1 , ring C 2 , and ring C 3 are each independently 1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, tetrahydropyran-2,5-diyl, or 1,4-phenylene in which arbitrary hydrogen is replaced by fluorine;

Z 6 is —(CH 2 ) 2 —, —COO—, —CF 2 O—, —OCF 2 —, —C≡C—, —CH 2 O—, or a single bond;

L 5 and L 6 are each independently hydrogen or fluorine; and

q is an integer of 0 to 2 and r is 0 or 1.

29. The liquid crystal composition according to claim 19 , further comprising at least one compound selected from the group of compounds each represented by formulas (11), (12), and (13):

wherein R 5 and R 6 are each independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl, arbitrary hydrogen may be replaced by fluorine, and arbitrary —CH 2 — may be replaced by —O—;

ring E 1 , ring E 2 , and ring E 3 are each independently 1,4-cyclohexylene, pyrimidine-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene; and

Z 9 and Z 10 are each independently —C≡C—, —COO—, —(CH 2 ) 2 —, —CH═CH—, or a single bond, and Z 11 is —COO— or a single bond.