Polymerizable polar compound, liquid crystal composition and liquid crystal display element
To provide a polar compound having high chemical stability, a high ability to align liquid crystal molecules, and high solubility in a liquid crystal composition, and a high voltage holding ratio of a liquid crystal display element. A compound represented by Formula (1): R 1 is a hydrogen atom or an alkyl group that may be substituted; a is 2 to 12; and R 2 is Formula (1-a), Formula (1-b), and Formula (1-c); Sp 1 to Sp 3 are a single bond or an alkylene group that may be substituted; M 1 and M 2 are H, F, Cl, or an alkyl group that may be substituted; and X 1 is —OH, —NH 2 , —OR 3 , —N(R 3 ) 2 , —COOH, —SH or —Si(R 3 ) 3 .
1. A compound represented by Formula (1):
in Formula (1),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O— or —S—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH— or —C≡C—, and in these groups represented by R 1 , at least one hydrogen atom is optionally substituted with a fluorine or chlorine atom;
a is an integer of 2 to 12;
M 1 and M 2 are independently a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is substituted with a fluorine atom or a chlorine atom; and
R 2 is a group selected from among groups represented by Formula (1-a), Formula (1-b), and Formula (1-c);
in Formula (1-a), Formula (1-b), and Formula (1-c),
Sp 2 and Sp 3 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH— or —C≡C—, and in these groups represented by Sp 2 and Sp 3 , at least one hydrogen atom is optionally substituted with a fluorine or chlorine atom;
R 3 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, or an alkoxyalkyl group having 1 to 9 carbon atoms;
X 1 is independently —OH, —NH 2 , —N(R 4 ) 2 , —COOH, —SH, or —Si(R 4 ) 3 ;
in —N(R 4 ) 2 , and —Si(R 4 ) 3 ,
R 4 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by R 4 , at least one hydrogen atom is optionally substituted with a fluorine or chlorine atom,
in Formula (1),
Sp 1 is a single bond or an alkylene group having 1 to 15 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH— or —C≡C—, and in these groups represented by Sp 1 , at least one hydrogen atom is optionally substituted with a fluorine atom, a chlorine atom, or a group represented by Formula (1-d);
in Formula (1-d),
Sp 4 is a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH— or —C≡C—, and in these groups represented by Sp 4 , at least one hydrogen atom is optionally substituted with a fluorine or chlorine atom;
M 3 and M 4 are independently a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is substituted with a fluorine atom or a chlorine atom; and
R 5 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH— or —C≡C—, and at least one hydrogen atom is optionally substituted with a fluorine atom or a chlorine atom.
2. The compound according to claim 1 , wherein, in Formula (1), R 2 is a group represented by Formula (1-a) or Formula (1-b).
3. The compound according to claim 1 , wherein, in Formula (1), R 2 is a group represented by Formula (1-a) or Formula (1-b), and in Formula (1-a) and Formula (1-b), X 1 is independently —OH, —NH 2 , —COOH, or —SH.
4. The compound according to claim 1 , which is represented by any one of Formula (1-1) to Formula (1-6):
in Formula (1-1) to Formula (1-6),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by R 1 , at least one hydrogen atom is optionally substituted with a fluorine atom;
a is an integer of 2 to 8;
Sp 1 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by Sp 1 , Sp 2 , Sp 3 , and Sp 4 , at least one hydrogen atom is optionally substituted with a fluorine atom;
Sp 5 and Sp 6 are independently a single bond or an alkylene group having 1 to 7 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by Sp 5 and Sp 6 , at least one hydrogen atom is optionally substituted with a fluorine atom;
R 3 is a hydrogen, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkoxyalkyl group having 1 to 6 carbon atoms;
R 5 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
5. The compound according to claim 1 , which is represented by any one of Formula (1-7) to Formula (1-24):
in Formula (1-7) to Formula (1-24),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—;
a is an integer of 2 to 8;
Sp 1 is a single bond or an alkylene group having 1 to 7 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—; and
R 3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
6. The compound according to claim 1 , which is represented by any one of Formula (1-25) to Formula (1-48):
in Formula (1-25) to Formula (1-48),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—;
Sp 1 is a single bond or an alkylene group having 1 to 7 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—.
7. The compound according to claim 1 , which is represented by any one of Formula (1-49) to Formula (1-56):
in Formula (1-49) to Formula (1-56),
R 1 is an alkyl group having 1 to 10 carbon atoms.
8. A liquid crystal composition comprising at least one compound according to claim 1 .
9. The liquid crystal composition according to claim 8 , which comprises at least one compound selected from the group of compounds represented by Formulae (2) to (4):
in Formulae (2) to (4),
R 11 and R 12 are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in these alkyl and alkenyl groups, at least one —CH 2 — is optionally substituted with —O—, and in these groups represented by R 11 and R 12 , at least one hydrogen atom is optionally substituted with a fluorine atom;
the ring B 1 , the ring B 2 , the ring B 3 , and the 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, —COO—, —CH 2 CH 2 —, —CH═CH—, or —C≡C—.
10. The liquid crystal composition according to claim 8 , which comprises at least one compound selected from the group of compounds represented by Formulae (5) to (7):
in Formulae (5) to (7),
R 13 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in these alkyl and alkenyl groups, at least one —CH 2 — is optionally substituted with —O—, and in these groups represented by R 13 , at least one hydrogen atom is optionally substituted with a fluorine atom;
X 11 is a fluorine atom, a chlorine atom, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2, —CH 2 F, —OCF 2 CHF 2 , or —OCF 2 CHFCF 3 ;
the ring C 1 , the ring C 2 , and the ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene in which at least one hydrogen atom is substituted with a fluorine atom;
Z 14 , Z 15 , and Z 16 are independently a single bond, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CH═CH—, —C≡C—, or —(CH 2 ) 4 —; and
L 11 and L 12 are independently a hydrogen atom or a fluorine atom.
11. The liquid crystal composition according to claim 8 , which comprises at least one compound selected from the group of compounds represented by Formula (8):
in Formula (8),
R 14 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in these alkyl and alkenyl groups, at least one —CH 2 — is optionally substituted with —O—, and in these groups represented by R 14 , at least one hydrogen atom is optionally substituted with a fluorine atom;)
X 12 is —C≡N or —C≡C—C≡N;
the ring D 1 is 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene in which at least one hydrogen atom is substituted with a fluorine atom;
Z 17 is a single bond, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, or —C≡C—;
L 13 and L 14 are independently a hydrogen atom or a fluorine atom; and
i is 1, 2, 3, or 4.
12. The liquid crystal composition according to claim 8 , which comprises at least one compound selected from the group of compounds represented by Formulae (11) to (19):
in Formulae (11) to (19),
R 15 , R 16 , and R 17 are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in these alkyl and alkenyl groups, at least one —CH 2 — is optionally substituted with —O—, and in these groups represented by R 15 , R 16 , and R 17 , at least one hydrogen atom is optionally substituted with a fluorine atom, and R 17 may be a hydrogen atom or a fluorine atom;
the ring E 1 , the ring E 2 , the ring E 3 , and the ring E 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, decahydronaphthalene-2,6-diyl, or 1,4-phenylene in which at least one hydrogen atom is substituted with a fluorine atom;
the ring E 5 and the 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, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 OCH 2 CH 2 —, or —OCF 2 CH 2 CH 2 —;
L 15 and L 16 are independently a fluorine atom or a chlorine atom;
S 11 is a hydrogen atom or a methyl group;
X is —CHF— or —CF 2 —;
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, and a sum of q, r, and s is 0, 1, 2, or 3, and
t is 1, 2, or 3.
13. The liquid crystal composition according to claim 8 , which comprises at least one polymerizable compound represented by Formula (20) other than the compound represented by Formula (1):
in Formula (20),
the ring F and the ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl, or pyridin-2-yl, and in these rings, at least one hydrogen atom is optionally substituted with a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom;
the ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, phenanthrene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, and in these rings, at least one hydrogen atom is optionally substituted with a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom;
Z 22 and Z 23 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, —CO—, —COO—, or —OCO—, and at least one —CH 2 CH 2 — is optionally substituted with —CH═CH—, —C(CH 3 )═CH—, —CH═C(CH 3 )—, or —C(CH 3 )═C(CH 3 )—, and in these groups represented by Z 22 and Z 23 , at least one hydrogen atom is optionally substituted with a fluorine or chlorine atom;
P 11 , P 12 , and P 13 are independently a polymerizable group;
Sp 11 , Sp 12 , and Sp 13 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, —COO—, —OCO—, or —OCOO—, and at least one —CH 2 CH 2 — is optionally substituted with —CH═CH— or —C≡C—, and in these groups represented by Sp 11 , Sp 12 , and Sp 13 , at least one hydrogen atom is optionally substituted with a fluorine or chlorine atom;
u is 0, 1, or 2; and
f, g, and h are independently 0, 1, 2, 3, or 4, and a sum of f, g, and h is 1 or more.
14. The liquid crystal composition according to claim 13 , wherein, in Formula (20), P 11 , P 12 , and P 13 are independently a group selected from the group of polymerizable groups represented by Formula (P-1) to Formula (P-5):
in Formula (P-1) to Formula (P-5),
M 11 , M 12 , and M 13 are independently a hydrogen atom, a fluorine atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom.
15. The liquid crystal composition according to claim 13 , wherein the polymerizable compound represented by Formula (20) is at least one compound selected from the group of polymerizable compounds represented by Formula (20-1) to Formula (20-7):
in Formula (20-1) to Formula (20-7),
L 31 , L 32 , L 33 , L 34 , L 35 , L 36 , L 37 , and L 38 are independently a hydrogen atom, a fluorine atom, or a methyl group;
Sp 11 , Sp 12 , and Sp 13 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, —COO—, —OCO—, or —OCOO—, and at least one —CH 2 CH 2 — is optionally substituted with —CH═CH— or —C≡C—, and in these groups represented by Sp 11 , Sp 12 , and Sp 13 , at least one hydrogen atom is optionally substituted with a fluorine atom or a chlorine atom;
P 11 , P 12 , and P 13 are independently a group selected from the group of polymerizable groups represented by Formula (P-1) to Formula (P-3),
in Formula (P-1) to Formula (P-3),
M 11 , M 12 , and M 13 are independently a hydrogen atom, a fluorine atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom.
16. The liquid crystal composition according to claim 13 , which comprises at least one selected from the group consisting of a polymerizable compound different from the compound represented by Formula (1) or Formula (20), a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, a UV absorber, a light stabilizer, a heat stabilizer, a dye, and an antifoaming agent.
17. A liquid crystal display element including a product obtained by polymerizing the liquid crystal composition according to claim 8 .
18. The compound according to claim 2 , which is represented by any one of Formula (1-1) to Formula (1-6):
in Formula (1-1) to Formula (1-6),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by R 1 , at least one hydrogen atom is optionally substituted with a fluorine atom;
a is an integer of 2 to 8;
Sp 1 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 - is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by Sp 1 , Sp 2 , Sp 3 , and Sp 4 , at least one hydrogen atom is optionally substituted with a fluorine atom;
Sp 5 and Sp 6 are independently a single bond or an alkylene group having 1 to 7 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by Sp 5 and Sp 6 , at least one hydrogen atom is optionally substituted with a fluorine atom;
R 3 is a hydrogen, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkoxyalkyl group having 1 to 6 carbon atoms;
R 5 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
19. The compound according to claim 3 , which is represented by any one of Formula (1-1) to Formula (1-6):
in Formula (1-1) to Formula (1-6),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by R 1 , at least one hydrogen atom is optionally substituted with a fluorine atom;
a is an integer of 2 to 8;
Sp 1 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in this alkylene group, at least one —CH 2 - is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by Sp 1 , Sp 2 , Sp 3 , and Sp 4 , at least one hydrogen atom is optionally substituted with a fluorine atom;
Sp 5 and Sp 6 are independently a single bond or an alkylene group having 1 to 7 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—, and in these groups represented by Sp 5 and Sp 6 , at least one hydrogen atom is optionally substituted with a fluorine atom;
R 3 is a hydrogen, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkoxyalkyl group having 1 to 6 carbon atoms;
R 5 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
20. The compound according to claim 2 , which is represented by any one of Formula (1-7) to Formula (1-24):
in Formula (1-7) to Formula (1-24),
R 1 is an alkyl group having 1 to 15 carbon atoms, and in this alkyl group, at least one —CH 2 — is optionally substituted with —O—, and at least one —(CH 2 ) 2 — is optionally substituted with —CH═CH—;
a is an integer of 2 to 8;
Sp 1 is a single bond or an alkylene group having 1 to 7 carbon atoms, and in this alkylene group, at least one —CH 2 — is optionally substituted with —O—; and
R 3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.