Dihydropyran compound, liquid crystal composition and liquid crystal display device

1. A compound represented by formula (1):

wherein, in formula (1),

R a and R b are independently alkyl having 1 to 10 carbons, and in the alkyl, at least one of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, and at least one of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—;

ring A 1 , A 2 , A 3 and A 4 are independently 1,4-cyclohexylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-xanthene-2,6-diyl or 9H-fluorene-2,7-diyl, and in the groups, at least one of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one of —CH 2 CH 2 — may be replaced by —CH═CH— or —CH═N—, and in the divalent groups, at least one of hydrogen may be replaced by fluorine, chlorine, —C≡N, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 or —OCH 2 F; and

P is a divalent group represented by formula (pr-1) or (pr-2):

wherein, Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond or alkylene having 1 to 6 carbons, and in the alkylene, at least one of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, one or two of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the divalent groups, at least one of hydrogen may be replaced by fluorine or chlorine;

a, b, c and d are independently 0, 1 or 2, and a sum of a, b, c and d is 5 or less;

however, when P is represented by formula (pr-1), R a is alkyl, R b is alkoxy, a is 1, b is 0, c and d are 1, A 1 is cyclohexylene, A 3 and A 4 are 2,3-difluorophenylene, Z 1 and Z 4 are a single bond and Z 3 is alkylene having 2 carbons, in the alkylene, at least one of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, or one of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the divalent groups, at least one of hydrogen may be replaced by fluorine or chlorine;

moreover, when P is represented by formula (pr-2), R a is alkoxy, R b is alkyl, a and b are 1, c is 1, d is 0, A 1 and A 2 are 2,3-difluorophenylene, A 3 is cyclohexylene, Z 1 and Z 3 are a single bond and Z 2 is alkylene having 2 carbons, in the alkylene, at least one of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, or one of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the divalent groups, at least one of hydrogen may be replaced by fluorine or chlorine.

2. The compound according to claim 1 , represented by formulas (1-1) to (1-3):

wherein, in formulas (1-1) to (1-3),

R a and R b are independently hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one of —CH 2 — may be replaced by —O— or —S—, and at least one of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—;

ring A 1 and A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexene-1,4-diyl, tetrahydropyran-2,5-diyl, tetrahydro-2H-pyran-2-one-3,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2-chloro-1,4-phenylene, 2-fluoro-3-chloro-1,4-phenylene, 2,3-dichloro-1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl or naphthalene-2,6-diyl, and in the divalent groups, at least one of hydrogen may be replaced by fluorine, chlorine, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 or —OCH 2 F; and

P is a divalent group represented by formula (pr-1) or (pr-2):

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

Y 1 , Y 2 and Y 3 are independently hydrogen, fluorine, chlorine, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 or —OCH 2 F; and

a and b are independently 0, 1, 2 or 3, and a sum of a and b is 4 or less; and

in formula (1-1), when R a is alkyl, R b is alkoxy, a and b are 1, A 1 is cyclohexylene, A 2 is 2,3-difluorophenylene, Z 1 and Z 3 are a single bond, Z 2 is —CH 2 CH 2 — and Y 1 and Y 2 are fluorine, P is a divalent group represented by formula (pr-2).

3. The compound according to claim 2 , represented by any one of formulas (1-11a) to (1-13a) and formulas (1-11b) to (1-13b):

wherein, in formulas (1-11a) to (1-13a) and formulas (1-11b) to (1-13b),

R a and R b are independently alkyl having 1 to 10 carbons, and in the alkyl, one or two of —CH 2 — may be replaced by —O— or —S—, and one or two of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—;

ring A 1 and A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexene-1,4-diyl, tetrahydropyran-2,5-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2-chloro-1,4-phenylene, 2-fluoro-3-chloro-1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl or naphthalene-2,6-diyl;

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

Y 1 and Y 2 are independently fluorine or chlorine.

4. The compound according to claim 3 , wherein, in formulas (1-11a) to (1-13a) and formulas (1-11b) to (1-13b),

R a and R b are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons;

ring A 1 and A 2 are independently 1,4-cyclohexylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2-chloro-1,4-phenylene, 2-fluoro-3-chloro-1,4-phenylene or pyrimidine-2,5-diyl;

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

Y 1 and Y 2 are independently fluorine or chlorine.

5. The compound according to claim 2 , represented by any one of formulas (1-21a) to (1-23a) and formulas (1-21b) to (1-23b):

wherein, in formulas (1-21a) to (1-23a) and formulas (1-21b) to (1-23b),

R a and R b are independently alkyl having 1 to 10 carbons, and in the alkyl, one or two of —CH 2 — may be replaced by —O— or —S—, and one or two of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—;

ring A 1 and A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexene-1,4-diyl, tetrahydropyran-2,5-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2-chloro-1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl or naphthalene-2,6-diyl;

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

Y 1 and Y 3 are independently hydrogen, fluorine or chlorine.

6. The compound according to claim 5 , wherein, in formulas (1-21a) to (1-23a) and formulas (1-21b) to (1-23b),

R a and R b are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons;

ring A 1 and A 2 are independently 1,4-cyclohexylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2-chloro-1,4-phenylene or pyrimidine-2,5-diyl;

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

Y 1 and Y 3 are independently hydrogen or fluorine.

7. The compound according to claim 2 , represented by any one of formulas (1-31) to (1-36):

wherein, in formulas (1-31) to (1-36),

R a and R b are independently alkyl having 1 to 10 carbons, and in the alkyl, one or two of —CH 2 — may be replaced by —O— or —S—, and one or two of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—;

ring A 1 and A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexene-1,4-diyl, tetrahydropyran-2,5-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2-chloro-1,4-phenylene, 2-fluoro-3-chloro-1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl or naphthalene-2,6-diyl; and

P is a divalent group represented by formula (pr-1) or (pr-2):

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

8. The compound according to claim 2 , represented by any one of formulas (1-14) to (1-16) and formulas (1-24) to (1-26):

wherein, in formulas (1-14) to (1-16) and formulas (1-24) to (1-26),

R a and R b are independently alkyl having 1 to 10 carbons, and in the alkyl, one or two of —CH 2 — may be replaced by —O— or —S—, and one or two of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—;

ring A 1 and A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexene-1,4-diyl, tetrahydropyran-2,5-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2-chloro-1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl or naphthalene-2,6-diyl; and

P is a divalent group represented by formula (pr-1) or (pr-2):

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

in formulas (1-14) to (1-16), Y 1 and Y 2 are independently fluorine or chlorine, and in formulas (1-24) to (1-26), Y 1 and Y 3 are independently hydrogen, fluorine or chlorine.

9. The compound according to claim 8 , wherein, in formulas (1-14) to (1-16) and formulas (1-24) to (1-26) according to claim 8 ,

R a and R b are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons;

ring A 1 and A 2 are independently 1,4-cyclohexylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2-chloro-1,4-phenylene or pyrimidine-2,5-diyl;

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

Y 1 and Y 2 are independently hydrogen or fluorine.

10. The compound according to claim 2 , represented by any one of formula (1-111a), formula (1-121a), formula (1-131a), formula (1-141a), formula (1-151a), formula (1-161a), formula (1-111b), formula (1-121b), formula (1-131b), formula (1-141b), formula (1-151b) and formula (1-161b):

wherein, in formula (1-111a), formula (1-121a), formula (1-131a), formula (1-141a), formula (1-151a), formula (1-161a), formula (1-111b), formula (1-121b), formula (1-131b), formula (1-141b), formula (1-151b) and formula (1-161b), R e and R g are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons; and

ring A 5 is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene.

11. The compound according to claim 2 , represented by any one of formula (1-211a), formula (1-212a), formula (1-213a), formula (1-231a), formula (1-311a), formula (1-331a), formula (1-361a), formula (1-211b), formula (1-212b), formula (1-213b), formula (1-231b), formula (1-311b), formula (1-331b) and formula (1-361b):

wherein, R h and R k are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons; and

ring A 6 is 1,4-cyclohexylene, 1,4-phenylene or 2-fluoro-1,4-phenylene; and ring A 7 is 1,4-phenylene or 2-fluoro-1,4-phenylene.

12. A liquid crystal composition, containing the compound according to claim 2 .

13. A liquid crystal composition having a nematic phase and containing at least one compound selected from the group of compounds represented by formula (1) as a first component and at least one compound selected from the group of compounds represented by formulas (2) to (4) as a second component:

wherein, in formula (1),

R a and R h are independently alkyl having 1 to 10 carbons, and in the alkyl, at least one of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, and at least one of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—;

ring A 1 , A 2 , A 3 and A 4 independently 1,4-cyclohexylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-xanthene-2,6-diyl or 9H-fluorene-2,7-diyl, and in the groups, at least one of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one of —CH 2 CH 2 — may be replaced by —CH═CH— or —CH═N—, and in the divalent groups, at least one of hydrogen may be replaced by fluorine, chlorine, —C≡N, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 or —OCH 2 F; and

P is a divalent group represented by formula (pr-1) or (pr-2):

wherein, Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond or alkylene having 1 to 6 carbons, and in the alkylene, at least one of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, one or two of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the divalent groups, at least one of hydrogen may be replaced by fluorine or chlorine; and

a, b, c and d are independently 0, 1 or 2, and a sum of a, b, c and d is 5 or less;

wherein, in formulas (2) to (4),

R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl or the alkenyl, at least one of —CH 2 — may be replaced by —O—, and at least one of hydrogen may be replaced by fluorine;

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

Z 11 , Z 12 and Z 13 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C— or —COO—.

14. The liquid crystal composition according to claim 13 , further containing at least one compound selected from the group of compounds represented by formulas (5) to (7) as a third component:

wherein, in formulas (5) to (7),

R 13 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of —CH 2 — may be replaced by —O—, and at least one of hydrogen may be replaced by fluorine;

X 11 is fluorine, chlorine, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 or —OCF 2 CHFCF 3 ;

ring C 1 , ring C 2 and ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one of hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

Z 14 , Z 15 and Z 16 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —CF 2 O—, —OCF 2 —, —CH 2 O— or —(CH 2 ) 4 —; and

L 11 and L 12 are independently hydrogen or fluorine.

15. The liquid crystal composition according to claim 13 , further containing at least one compound selected from the group of compounds represented by formula (8) as the third component:

wherein, in formula (8),

R 14 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of —CH 2 — may be replaced by —O—, and at least one of hydrogen may be replaced by fluorine;

X 12 is —C≡N or —C≡C—C≡N;

ring D 1 is 1,4-cyclohexylene, 1,4-phenylene in which at least one of hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

Z 17 is a single bond, —CH 2 CH 2 —, —COO—, —CF 2 O—, —OCF 2 — or —CH 2 O—;

L 13 and L 14 are independently hydrogen or fluorine; and

i is 1, 2, 3 or 4.

16. The liquid crystal composition according to claim 13 , further containing at least one compound selected from the group of compounds represented by formulas (9) to (15) as the third component:

wherein, in formulas (9) to (15),

R 15 and R 16 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of —CH 2 — may be replaced by —O—, and at least one of hydrogen may be replaced by fluorine;

R 17 is hydrogen, fluorine, alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of —CH 2 — may be replaced by —O—, and at least one of hydrogen may be replaced by fluorine;

ring E 1 , ring E 2 , ring E 3 and ring E 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one of hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl;

ring E 5 and ring E 6 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl;

Z 18 , Z 19 , Z 20 and Z 21 are independently a single bond, —CH 2 CH 2 —, —COO—, —CH 2 O—, —OCF 2 — or —OCF 2 CH 2 CH 2 —;

L 15 and L 16 are independently fluorine or chlorine;

S 11 is hydrogen or methyl;

X is —CHF— or —CF 2 —; and

j, k, m, n, p, q, r and s are independently 0 or 1, a sum of k, m, n and p is 1 or 2, a sum of q, r and s is 0, 1, 2 or 3, and t is 1, 2 or 3.

17. A liquid crystal display device, including the liquid crystal composition according to claim 12 .