POLYMERIZABLE POLAR COMPOUND, LIQUID CRYSTAL COMPOSITION, AND LIQUID CRYSTAL DISPLAY ELEMENT

Abstract

Compound (1) is provided.

R.sup.1-MES-Sp.sup.1-P.sup.1(1)

In compound (1), R.sup.1 is alkyl having 1 to 15 carbons; MES is a mesogen group having an at least one ring; Sp.sup.1 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one hydrogen is replaced by group (1a); P.sup.1 is group (1e) or (1f);

##STR00001##

wherein, M.sup.1, M.sup.2, M.sup.3 and M.sup.4 are hydrogen; Sp.sup.2 and Sp.sup.3 are a single bond or alkylene having 1 to 10 carbons; R.sup.2 is alkyl having 1 to 15 carbons; R.sup.3 is group (1g), (1h) or (1i);

##STR00002##

wherein, Sp.sup.4 and Sp.sup.5 are a single bond or alkylene having 1 to 10 carbons; S.sup.1 is >CH, and S.sup.2 is >C<; and X is OH.

Claims

1. A compound, represented by formula (1):
R.sup.1-MES-Sp.sup.1-P.sup.1(1) wherein, in formula (1), R.sup.1 is alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O or S, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by halogen; MES is a mesogen group having at least one ring; Sp.sup.1 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by halogen, and in the groups, at least one hydrogen is replaced by a group selected from groups represented by formula (1a), formula (1b), formula (1c) and formula (1 d); ##STR00421## wherein, in formula (1a), formula (1b), formula (1c) and formula (1d), Sp.sup.2 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by halogen; M.sup.1 and M.sup.2 are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen; R.sup.2 is hydrogen or alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O or S, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by halogen; and in formula (1), P.sup.1 is a group selected from groups represented by formula (1e) and formula (1f); ##STR00422## wherein, in formula (1e) and (1f), Sp.sup.3 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, NH, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by halogen; M.sup.3 and M.sup.4 are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen; X.sup.1 is OH, NH.sub.2, OR.sup.5, N(R.sup.5).sub.2, COOH, SH, B(OH).sub.2 or Si(R.sup.5).sub.3; and R.sup.3 is a group selected from groups represented by formula (1g), formula (1h) and formula (1i); ##STR00423## wherein, in formula (1g), formula (1h) and formula (1i), Sp.sup.4 and Sp.sup.5 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, NH, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by halogen; S.sup.1 is >CH or >N; S.sup.2 is >C< or >Si<; X.sup.1 is OH, NH.sub.2, OR.sup.5, N(R.sup.5).sub.2, COOH, SH, B(OH).sub.2 or Si(R.sup.5).sub.3; and in OR.sup.5, N(R.sup.5).sub.2 and Si(R.sup.5).sub.3, R.sup.5 is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH, and in the groups, at least one hydrogen may be replaced by halogen.

2. The compound according to claim 1, represented by formula (1-1): ##STR00424## wherein, in formula (1-1), R.sup.1 is alkyl having 1 to 12 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; ring A.sup.1 and ring A.sup.2 are independently 1,4-cycloxylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl, or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, 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, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; a is 0, 1, 2, 3 or 4; Z.sup.1 is a single bond or alkylene having 1 to 6 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; Sp.sup.1 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine, and in the groups, at least one hydrogen is replaced by a polymerizable group represented by formula (1a); ##STR00425## wherein, in formula (1a), Sp.sup.2 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, NH, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by halogen; M.sup.1 and M.sup.2 are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; R.sup.2 is hydrogen or alkylene having 1 to 15 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O or S, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; and in formula (1-1), P.sup.1 is a group selected from groups represented by formula (1e) and formula (1f); ##STR00426## wherein, in formula (1e) and formula (1f), Sp.sup.3 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, NH, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; M.sup.3 and M.sup.4 are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; X.sup.1 is OH, NH.sub.2, OR.sup.5, N(R.sup.5).sub.2, COOH, SH or Si(R.sup.5).sub.3; and R.sup.3 is a group selected from groups represented by formula (1g) and formula (1h); ##STR00427## wherein, in formula (1g) and formula (1h), Sp.sup.4 and Sp.sup.5 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, NH, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; S.sup.1 is >CH or >N; X.sup.1 is OH, NH.sub.2, OR.sup.5, N(R.sup.5).sub.2, COOH, SH or Si(R.sup.5).sub.3; and in OR.sup.5, N(R.sup.5).sub.2 and Si(R.sup.5).sub.3, R.sup.5 is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine.

3. The compound according to claim 2, wherein, in formula (1-1), Z.sup.1 is a single bond, (CH.sub.2).sub.2, (CH.sub.2).sub.4, CHCH, CC, COO, OCO, CF.sub.2O, OCF.sub.2, CH.sub.2O, OCH.sub.2 or CFCF; and in formula (1a), M.sup.1 and M.sup.4 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine; and in formula (1e), M.sup.3 and M.sup.4 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine; and R.sup.3 is a group represented by formula (1g).

4. The compound according to claim 2, wherein, in formula (1-1), ring A.sup.1 and ring A.sup.2 are independently 1,4-cycloxylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyloxy having 2 to 9 carbons, and in the groups, at least one hydrogen may be replaced by fluorine; Sp.sup.1 is a single bond or alkylene having 1 to 8 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine, and in the groups, at least one hydrogen is replaced by a group represented by formula (1a); ##STR00428## wherein, in formula (1a), Sp.sup.2 is a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, NH, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by halogen; M.sup.1 and M.sup.2 are independently hydrogen, fluorine, methyl, ethyl or trifluoromethyl; R.sup.2 is hydrogen or alkylene having 1 to 8 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; and in formula (1-1) P.sup.1 is a group selected from groups represented by formula (1e) and formula (1f); ##STR00429## wherein, in formula (1e) and formula (1f), Sp.sup.3 is a single bond or alkylene having 1 to 5 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; M.sup.3 and M.sup.4 are independently hydrogen, fluorine, methyl, ethyl or trifluoromethyl; X.sup.1 is OH, NH.sub.2 or N(R.sup.5).sub.2; and R.sup.3 is a group represented by formula (1g);
-Sp.sup.4-X.sup.1 (1g) wherein, in formula (1g), Sp.sup.4 is a single bond or alkylene having 1 to 5 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; X.sup.1 is OH, NH.sub.2 or N(R.sup.5).sub.2; and in N(R.sup.5).sub.2, R.sup.5 is hydrogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH, and in the groups, at least one hydrogen may be replaced by fluorine.

5. The compound according to claim 1, represented by formula (1-2) or formula (1-3): ##STR00430## wherein, in formula (1-2) and formula (1-3), R.sup.1 is alkyl having 1 to 12 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; ring A.sup.1 and ring A.sup.2 are independently 1,4-cycloxylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, alkyl having 1 to 8 carbons, alkenyl having 2 to 8 carbons, alkoxy having 1 to 7 carbons or alkenyloxy having 2 to 7 carbons, and in the groups, at least one hydrogen may be replaced by fluorine; Z.sup.1 is a single bond, (CH.sub.2).sub.2, (CH.sub.2).sub.4, CHCH, CC, CF.sub.2O, OCF.sub.2, CH.sub.2O, OCH.sub.2 or CFCF; a is 0, 1, 2, 3 or 4; l is 0, 1, 2, 3, 4, 5 or 6, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; Sp.sup.2 is a single bond or alkylene having 1 to 5 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; M.sup.1 and M.sup.2 are independently hydrogen, fluorine, methyl, ethyl or trifluoromethyl; R.sup.2 is hydrogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O or S, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; Sp.sup.3 is a single bond or alkylene having 1 to 5 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO or COO, and in the groups, at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; M.sup.3 and M.sup.4 are independently hydrogen, fluorine, methyl, ethyl or trifluoromethyl; Sp.sup.4 is a single bond, alkylene having 1 to 5 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO or COO, and at least one piece of (CH.sub.2).sub.2-may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; X.sup.1 is OH or N(R.sup.5).sub.2; and in N(R.sup.5).sub.2, R.sup.5 is hydrogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH, and in the groups, at least one hydrogen may be replaced by fluorine.

6. The compound according to claim 5, wherein, in formula (1-2) and formula (1-3), R.sup.1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons, and in the groups, at least one hydrogen may be replaced by fluorine; ring A.sup.1 and ring A.sup.2 are independently 1,4-cycloxylene, 1,4-phenylene, naphthalene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 5 carbons; a is 0, 1, 2, 3 or 4; l is 0, 1, 2, 3, 4, 5 or 6, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine; Z.sup.1 is a single bond, (CH.sub.2).sub.2, (CH.sub.2).sub.4, CHCH, CF.sub.2O OCF.sub.2, CH.sub.2O or OCH.sub.2; Sp.sup.2 is a single bond or alkylene having 1 to 5 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH; M.sup.1 and M.sup.2 are independently hydrogen, methyl or ethyl; R.sup.2 is hydrogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH; Sp.sup.3 is a single bond or alkylene having 1 to 5 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH; M.sup.3 and M.sup.4 are independently hydrogen, fluorine, methyl or ethyl; Sp.sup.4 is a single bond or alkylene having 1 to 5 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH; X.sup.1 is OH or N(R.sup.5).sub.2; and in N(R.sup.5).sub.2, R.sup.5 is hydrogen or alkyl having 1 to 3 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O.

7. The compound according to claim 5, wherein, in formula (1-2) and formula (1-3), R.sup.1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons; ring A.sup.1 and ring A.sup.2 are independently 1,4-cycloxylene, 1,4-phenylene or naphthalene-2,6-diyl, and in the rings, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 5 carbons; a is 0, 1, 2 or 3; l is 0, 1, 2, 3, 4, 5 or 6, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO, OCO or OCOO, and at least one piece of (CH.sub.2).sub.2 may be replaced by CHCH or CC; Z.sup.1 is a single bond, (CH.sub.2).sub.2 or (CH.sub.2).sub.4; Sp.sup.2 is a single bond or alkylene having 1 to 3 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O; M.sup.1 and M.sup.2 are independently hydrogen or methyl; R.sup.2 is hydrogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one piece of CH.sub.2 may be replaced by O; Sp.sup.3 is a single bond or alkylene having 1 to 3 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O; M.sup.3 and M.sup.4 are independently hydrogen or methyl; Sp.sup.4 is a single bond or alkylene having 1 to 3 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O; and X.sup.1 is OH.

8. The compound according to claim 1, represented by any one of formula (1-4) to formula (1-41), formula (1-42) to formula (1-60), formula (1-61) to formula (1-98), and formula (1-99) to formula (1-117): ##STR00431## ##STR00432## ##STR00433## ##STR00434## ##STR00435## ##STR00436## ##STR00437## ##STR00438## ##STR00439## ##STR00440## ##STR00441## ##STR00442## ##STR00443## wherein, in formula (1-4) to formula (1-41), R.sup.1 is alkyl having 1 to 10 carbons; Z.sup.1, Z.sup.2 and Z.sup.3 are independently a single bond, (CH.sub.2).sub.2 or (CH.sub.2).sub.4; Sp.sup.2, Sp.sup.3 and Sp.sup.4 are independently alkylene having 1 to 5 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O; L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, L.sup.7, L.sup.8, L.sup.9, L.sup.10, L.sup.11 and L.sup.12 are independently hydrogen, fluorine, methyl or ethyl; and l is 0, 1, 2, 3, 4, 5 or 6, and in formula (1-42) to formula (1-60), R.sup.1 is alkyl having 1 to 10 carbons; Z.sup.1, Z.sup.2 and Z.sup.3 are independently a single bond, (CH.sub.2).sub.2 or (CH.sub.2).sub.4; Sp.sup.2, Sp.sup.3 and Sp.sup.4 are independently alkylene having 1 to 5 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O; L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, L.sup.7, L.sup.8, L.sup.9, L.sup.10, L.sup.11 and L.sup.12 are independently hydrogen, fluorine, methyl or ethyl; and l is 0, 1, 2, 3, 4, 5 or 6, and in formula (1-61) to formula (1-98), R.sup.1 is alkyl having 1 to 10 carbons; Sp.sup.2 and Sp.sup.3 are independently alkylene having 1 to 3 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O; L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, L.sup.7, L.sup.8, L.sup.9, L.sup.10, L.sup.11 and L.sup.12 are independently hydrogen, fluorine or methyl; and l is 1, 2, 3 or 4, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, and in formula (1-99) to formula (1-117), R.sup.1 is alkyl having 1 to 10 carbons; Sp.sup.2 and Sp.sup.3 are independently alkylene having 1 to 3 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O; L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, L.sup.7, L.sup.8, L.sup.9, L.sup.10, L.sup.11 and L.sup.12 are independently hydrogen, fluorine or methyl; and l is 1, 2, 3 or 4, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O.

9. (canceled)

10. (canceled)

11. (canceled)

12. A liquid crystal composition, containing at least one of the compounds according to claim 1.

13. The liquid crystal composition according to claim 12, further containing at least one compound selected from the group of compounds represented by formula (2) to formula (4): ##STR00444## wherein, in formula (2) to formula (4), R.sup.11 and R.sup.12 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 piece of CH.sub.2 may be replaced by O, and in the groups, at least one hydrogen may be replaced by fluorine; ring B.sup.1, ring B.sup.2, ring B.sup.3 and ring B.sup.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.sup.11, Z.sup.12 and Z.sup.13 are independently a single bond, CH.sub.2CH.sub.2, CHCH, CC or COO.

14. The liquid crystal composition according to claim 12, further containing at least one compound selected from the group of compounds represented by formula (5) to formula (7): ##STR00445## wherein, in formula (5) to formula (7), R.sup.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 piece of CH.sub.2 may be replaced by O, and in the groups, at least one hydrogen may be replaced by fluorine; X.sup.11 is fluorine, chlorine, OCF.sub.3, OCHF.sub.2, CF.sub.3, CHF.sub.2, CH.sub.2F, OCF.sub.2CHF.sub.2 or OCF.sub.2CHFCF.sub.3; ring C.sup.1, ring C.sup.2 and ring C.sup.3 are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; Z.sup.14, Z.sup.15 and Z.sup.16 are independently a single bond, CH.sub.2CH.sub.2, CHCH, CC, COO, CF2O, OCF2-, CH2O- or (CH.sub.2).sub.4; and L.sup.11 and L.sup.12 are independently hydrogen or fluorine.

15. The liquid crystal composition according to claim 12, further containing at least one compound of compounds represented by formula (8): ##STR00446## wherein, in formula (8), R.sup.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 piece of CH.sub.2 may be replaced by O, and in the groups, at least one hydrogen may be replaced by fluorine; X.sup.12 is CN or CCCN; ring D.sup.1 is 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; Z.sup.17 is a single bond, CH.sub.2CH.sub.2, CC, COO, CF.sub.2O, OCF.sub.2 or CH.sub.2O; L.sup.13 and L.sup.14 are independently hydrogen or fluorine; and i is 1, 2, 3 or 4.

16. The liquid crystal composition according to claim 12, further containing at least one compound selected from the group of compounds represented by formula (9) to formula (15): ##STR00447## wherein, in formula (9) to formula (15), R.sup.15, R.sup.16 and R.sup.17 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 piece of CH.sub.2 may be replaced by O, and in the groups, at least one hydrogen may be replaced by fluorine, and R.sup.17 may be hydrogen or fluorine; ring E.sup.1, ring E.sup.2, ring E.sup.3 and ring E.sup.4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl; ring E.sup.5 and ring E.sup.6 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl; Z.sup.18, Z.sup.19, Z.sup.20 and Z.sup.21 are independently a single bond, CH.sub.2CH.sub.2, COO, CH.sub.2O, OCF.sub.2 or OCF.sub.2CH.sub.2CH.sub.2; L.sup.15 and L.sup.16 are independently fluorine or chlorine; S.sup.11 is hydrogen or methyl; X is CHF or CF.sub.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. The liquid crystal composition according to claim 12, further containing at least one compound of polymerizable compounds represented by formula (16): ##STR00448## wherein, in formula (16), ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in the rings, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen; ring G is 1,4-cycloxylene, 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 the rings, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen; Z.sup.22 and Z.sup.23 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO or OCO, and at least one piece of CH.sub.2CH.sub.2 may be replaced by CHCH, C(CH.sub.3)CH, CHC(CH.sub.3) or C(CH.sub.3)C(CH.sub.3), and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; P.sup.11, P.sup.12 and P.sup.13 are independently a polymerizable group; Sp.sup.11, Sp.sup.12 and Sp.sup.13 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, COO, OCO or OCOO, and at least one piece of CH.sub.2CH.sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; 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.

18. The liquid crystal composition according to claim 17, wherein, in formula (16), P.sup.11, P.sup.12 and P.sup.13 are independently a group selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5): ##STR00449## wherein, in formula (P-1) to formula (P-5), M.sup.11, M.sup.12 and M.sup.13 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen.

19. The liquid crystal composition according to claim 17, wherein the polymerizable compound represented by formula (16) is at least one compound selected from the group of polymerizable compounds represented by formula (16-1) to formula (16-7): ##STR00450## wherein, in formula (16-1) to formula (16-7), L.sup.31, L.sup.32, L.sup.33, L.sup.34, L.sup.35, L.sup.35, L.sup.36, L.sup.37 and L.sup.38 are independently hydrogen, fluorine or methyl; Sp.sup.11, Sp.sup.12 and Sp.sup.13 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, COO, OCO or OCOO, and at least one piece of CH.sub.2CH.sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; and P.sup.11, P.sup.12 and P.sup.13 are independently a group selected from the group of polymerizable groups represented by formula (P-1) to formula (P-3): ##STR00451## wherein, in formula (P-1) to formula (P-3), M.sup.11, M.sup.12 and M.sup.13 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen.

20. The liquid crystal composition according to claim 12, further containing at least one of a polymerizable compound different from the compound represented by formula (1), or formula (16) described below, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet light absorber, a light stabilizer, a heat stabilizer and an antifoaming agent: ##STR00452## wherein, in formula (16), ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in the rings, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen; ring G is 1,4-cycloxylene, 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 the rings, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen; Z.sup.22 and Z.sup.23 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, CO, COO or OCO, and at least one piece of CH.sub.2CH.sub.2 may be replaced by CHCH, C(CH.sub.3)CH, CHC(CH.sub.3) or C(CH.sub.3)C(CH.sub.3), and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; P.sup.11, P.sup.12 and P.sup.13 are independently a polymerizable group; Sp.sup.11, Sp.sup.12 and Sp.sup.13 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of CH.sub.2 may be replaced by O, COO, OCO or OCOO, and at least one piece of CH.sub.2CH.sub.2 may be replaced by CHCH or CC, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; 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.

21. A liquid crystal display device, including at least one of the liquid crystal compositions according to claim 12.

Description

EXAMPLES

[0306] The invention will be described in greater detail by way of Examples (including Synthesis Examples and Use Examples). However, the invention is not limited by the Examples. The invention includes a mixture of a composition in Use Example 1 and a composition in Use Example 2. The invention also includes a mixture prepared by mixing at least two of the compositions in the Use Examples.

1. Example of Compound (1)

[0307] Unless otherwise described, a reaction was carried out under a nitrogen atmosphere. Compound (1) was prepared by a procedure shown in Example 1 or the like. The thus prepared compound was identified by methods such as an NMR analysis. Characteristics of compound (1), a liquid crystal compound, a composition and a device were measured according to methods described below.

[0308] NMR analysis: For measurement, DRX-500 made by Bruker BioSpin Corporation was used. In .sup.1H-NMR measurement, a sample was dissolved in a deuterated solvent such as CDCl.sub.3, and measurement was carried out under conditions of room temperature, 500 MHz and 16 times of accumulation. Tetramethylsilane was used as an internal standard. In .sup.19F-NMR measurement, CFCl.sub.3 was used as an internal standard, and measurement was carried out under conditions of 24 times of accumulation. In explaining nuclear magnetic resonance spectra obtained, s, d, t, q, quin, sex and m stand for a singlet, a doublet, a triplet, a quartet, a quintet, a sextet and a multiplet, and br being broad, respectively.

[0309] Gas chromatographic analysis: For measurement, GC-2010 Gas Chromatograph made by Shimadzu Corporation was used. As a column, a capillary column DB-1 (length 60 m, bore 0.25 mm, film thickness 0.25 m) made by Agilent Technologies, Inc. was used. As a carrier gas, helium (1 mL/minute) was used. A temperature of a sample vaporizing chamber was set to 300 C., and a temperature of a detector (FID) was set to 300 C. A sample was dissolved in acetone and prepared to be a 1 weight % solution, and then 1 microliter of the solution obtained was injected into the sample vaporizing chamber. As a recorder, GC Solution System made by Shimadzu Corporation or the like was used.

[0310] HPLC analysis: For measurement, Prominence (LC-20AD; SPD-20A) made by Shimadzu Corporation was used. As a column, YMC-Pack ODS-A (length 150 mm, bore 4.6 mm, particle diameter 5 m) made by YMC Co., Ltd. was used. As an eluate, acetonitrile and water were appropriately mixed and used. As a detector, a UV detector, an RI detector, a CORONA detector or the like was appropriately used. When the UV detector was used, a detection wavelength was set to 254 nanometers. A sample was dissolved in acetonitrile and prepared to be a 0.1 weight % solution, and then 1 microliter of the solution was introduced into a sample chamber. As a recorder, C-R7Aplus made by Shimadzu Corporation was used.

[0311] Ultraviolet-visible spectrophotometry: For measurement, PharmaSpec UV-1700 made by Shimadzu Corporation was used. A detection wavelength was adjusted in the range of 190 nanometers to 700 nanometers. A sample was dissolved in acetonitrile and prepared to be a 0.01 mmol/L solution, and measurement was carried out by putting the solution in a quartz cell (optical path length: 1 cm).

[0312] Sample for measurement: Upon measuring phase structure and a transition temperature (a clearing point, a melting point, a polymerization starting temperature or the like), the compound itself was used as a sample.

[0313] Measuring method: Characteristics were measured according to the methods described below. Most of the methods are described in the Standard of Japan Electronics and Information Technology Industries Association (hereinafter, abbreviated as JEITA) discussed and established in JEITA (JEITA ED-2521B), or modified thereon. No thin film transistor (TFT) was attached to a TN device used for measurement.

(1) Phase Structure

[0314] A sample was placed on a hot plate of a melting point apparatus (FP-52 Hot Stage made by Mettler-Toledo International Inc.) equipped with a polarizing microscope. A state of phase and a change thereof were observed with the polarizing microscope while the sample was heated at a rate of 3 C. per minute, and a kind of the phase was specified.

(2) Transition Temperature ( C.)

[0315] For measurement, a scanning calorimeter, Diamond DSC System, made by PerkinElmer, Inc., or a high sensitivity differential scanning calorimeter, X-DSC7000, made by SSI NanoTechnology Inc. was used. A sample was heated and then cooled at a rate of 3 C. per minute, and a starting point of an endothermic peak or an exothermic peak caused by a phase change of the sample was determined by extrapolation, and thus a transition temperature was determined. A melting point and a polymerization starting temperature of a compound were also measured using the apparatus. Temperature at which a compound undergoes transition from a solid to a liquid crystal phase such as a smectic phase and a nematic phase may be occasionally abbreviated as minimum temperature of the liquid crystal phase. Temperature at which the compound undergoes transition from the liquid crystal phase to liquid may be occasionally abbreviated as clearing point.

[0316] A crystal was expressed as C. When kinds of the crystals were distinguishable, each of the crystals was expressed as C.sup.1 or C.sub.2. The smectic phase or the nematic phase was expressed as S or N. When a smectic A phase, a smectic B phase, a smectic C phase or a smectic F phase was distinguishable among the smectic phases, the phases were expressed as S.sub.A, S.sub.B, S.sub.C or S.sub.F, respectively. A liquid (isotropic) was expressed as I. A transition temperature was expressed as C 50.0 N 100.0 I, for example. The expression indicates that a transition temperature from the crystals to the nematic phase is 50.0 C., and a transition temperature from the nematic phase to the liquid is 100.0 C.

(3) Maximum Temperature of Nematic Phase (T.SUB.NI .or NI; C.)

[0317] A sample was placed on a hot plate in a melting point apparatus equipped with a polarizing microscope, and heated at a rate of 1 C. per minute. Temperature when part of the sample changed from a nematic phase to an isotropic liquid was measured. A maximum temperature of the nematic phase may be occasionally abbreviated as maximum temperature. When the sample was a mixture of compound (1) and the base liquid crystal, the maximum temperature was expressed in terms of a symbol T.sub.NI. When the sample was a mixture of compound (1) and a compound such as component B, compound C and compound D, the maximum temperature was expressed using a symbol NI.

(4) Minimum Temperature of a Nematic Phase (T.SUB.C.; C.)

[0318] Samples each having a nematic phase were put in glass vials and kept in freezers at temperatures of 0 C., 10 C., 20 C., 30 C. and 40 C. for 10 days, and then liquid crystal phases were observed. For example, when the sample was maintained in the nematic phase at 20 C. and changed to crystals or a smectic phase at 30 C., T.sub.C was expressed as T.sub.C20 C. A minimum temperature of the nematic phase may be occasionally abbreviated as minimum temperature.

(5) Viscosity (Bulk Viscosity; r; Measured at 20 C.; mPa.Math.s)

[0319] For measurement, a cone-plate (E type) rotational viscometer made by Tokyo Keiki Inc. was used.

(6) Optical Anisotropy (Refractive Index Anisotropy; n; Measured at 25 C.)

[0320] Measurement was carried out by an Abbe refractometer with a polarizing plate mounted on an ocular, using light at a wavelength of 589 nanometers. A surface of a main prism was rubbed in one direction, and then a sample was added dropwise onto the main prism. A refractive index (n) was measured when a direction of polarized light was parallel to a direction of rubbing. A refractive index (n) was measured when the direction of polarized light was perpendicular to the direction of rubbing. A value of optical anisotropy was calculated from an equation: n=nn.

(7) Specific Resistance (; Measured at 25 C.; cm)

[0321] Into a vessel equipped with electrodes, 1.0 milliliter of a sample was injected. A direct current voltage (10V) was applied to the vessel, and a direct current after 10 seconds was measured. Specific resistance was calculated from the following equation: (specific resistance)={(voltage)(electric capacity of a vessel)}/{(direct current)(dielectric constant of vacuum)}.

[0322] The measuring method of the characteristics may be different between a sample having positive dielectric anisotropy and a sample having negative dielectric anisotropy. When the dielectric anisotropy was positive, the measuring method was described in measurement (8a) to measurement (12a). When the dielectric anisotropy was negative, the measuring method was described in measurement (8b) to measurement (12b).

(8a) Viscosity (Rotational Viscosity; 1; Measured at 25 C.; mPa.Math.s)

[0323] Positive dielectric anisotropy: Measurement was carried out according to a method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, p. 37 (1995). A sample was put in a TN device in which a twist angle was 0 degrees and a distance (cell gap) between two glass substrates was 5 micrometers. A voltage was applied stepwise to the device in the range of 16 V to 19.5 V at an increment of 0.5 V. After a period of 0.2 second with no voltage application, a voltage was repeatedly applied under conditions of only one rectangular wave (rectangular pulse; 0.2 second) and no voltage application (2 seconds). A peak current and a peak time of transient current generated by the applied voltage were measured. A value of rotational viscosity was obtained from the measured values and calculation equation (8) described on page 40 of the paper presented by M. Imai et al. A value of dielectric anisotropy required for the calculation was determined using the device by which the rotational viscosity was measured and by a method described below.

(8b) Viscosity (Rotational Viscosity; 1; Measured at 25 C.; mPa.Math.s)

[0324] Negative dielectric anisotropy: Measurement was carried out according to a method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, p. 37 (1995). A sample was put in a VA device in which a distance (cell gap) between two glass substrates was 20 micrometers. A voltage was applied stepwise to the device in the range of 39 V to 50 V at an increment of 1 V. After a period of 0.2 second with no voltage application, a voltage was repeatedly applied under conditions of only one rectangular wave (rectangular pulse; 0.2 second) and no voltage application (2 seconds). A peak current and a peak time of transient current generated by the applied voltage were measured. A value of rotational viscosity was obtained from the measured values and calculation equation (8) described on page 40 of the paper presented by M. Imai et al. As dielectric anisotropy required for the calculation, a value measured in a section of dielectric anisotropy described below was used.

(9a) Dielectric Anisotropy (; Measured at 25 C.)

[0325] Positive dielectric anisotropy: A sample was put in a TN device in which a distance (cell gap) between two glass substrates was 9 micrometers and a twist angle was 80 degrees. Sine waves (10 V, 1 kHz) were applied to the device, and after 2 seconds, a dielectric constant () of liquid crystal molecules in a major axis direction was measured. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, a dielectric constant () of liquid crystal molecules in a minor axis direction was measured. A value of dielectric anisotropy was calculated from an equation: =.

(9b) Dielectric Anisotropy (; Measured at 25 C.)

[0326] Negative dielectric anisotropy: A value of dielectric anisotropy was calculated from an equation: =. A dielectric constant ( and ) was measured as described below.

[0327] (1) Measurement of dielectric constant (): An ethanol (20 mL) solution of octadecyltriethoxysilane (0.16 mL) was applied to a well-cleaned glass substrate. After rotating the glass substrate with a spinner, the glass substrate was heated at 150 C. for 1 hour. A sample was put in a VA device in which a distance (cell gap) between two glass substrates was 4 micrometers, and the device was sealed with an ultraviolet-curable adhesive. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, a dielectric constant (ell) of liquid crystal molecules in a major axis direction was measured.

[0328] (2) Measurement of dielectric constant (): A polyimide solution was applied to a well-cleaned glass substrate. After calcining the glass substrate, rubbing treatment was applied to the alignment film obtained. A sample was put in a TN device in which a distance (cell gap) between two glass substrates was 9 micrometers and a twist angle was 80 degrees. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, a dielectric constant () of liquid crystal molecules in a minor axis direction was measured.

(10a) Elastic Constant (K; Measured at 25 C.; pN)

[0329] Positive dielectric anisotropy: For measurement, HP4284A LCR Meter made by Yokogawa-Hewlett-Packard Co. was used. A sample was put in a horizontal alignment device in which a distance (cell gap) between two glass substrates was 20 micrometers. An electric charge of 0 V to 20 V was applied to the device, and electrostatic capacity and applied voltage were measured. The measured values of electrostatic capacity (C) and applied voltage (V) were fitted to equation (2.98) and equation (2.101) on page 75 of Liquid Crystal Device Handbook (Ekisho Debaisu Handobukku in Japanese; The Nikkan Kogyo Shimbun, Ltd.) and values of K.sub.11 and K.sub.33 were obtained from equation (2.99). Next, K.sub.22 was calculated using the previously determined values of K.sub.11 and K.sub.33 in equation (3.18) on page 171. Elastic constant K was expressed in terms of a mean value of the thus determined K.sub.11, K.sub.22 and K.sub.33.

(10b) Elastic Constant (K.sub.11 and K.sub.33; Measured at 25 C.; pN)

[0330] Negative dielectric anisotropy: For measurement, Elastic Constant Measurement System Model EC-1 made by TOYO Corporation was used. A sample was put in a vertical alignment device in which a distance (cell gap) between two glass substrates was 20 micrometers. An electric charge of 20 V to 0 V was applied to the device, and electrostatic capacity and applied voltage were measured. The measured values of electrostatic capacity (C) and applied voltage (V) were fitted to equation (2.98) and equation (2.101) on page 75 of Liquid Crystal Device Handbook (Ekisho Debaisu Handobukku in Japanese; Nikkan Kogyo Shimbun, Ltd.), and values of elastic constant were obtained from equation (2.100).

(11a) Threshold voltage (Vth; measured at 25 C.; V)

[0331] Positive dielectric anisotropy: For measurement, an LCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used. A light source was a halogen lamp. A sample was put in a normally white mode TN device in which a distance (cell gap) between two glass substrates was 0.45/n (m) and a twist angle was 80 degrees. A voltage (32 Hz, rectangular waves) to be applied to the device was stepwise increased from 0 V to 10 V at an increment of 0.02 V. On the occasion, the device was irradiated with light from a direction perpendicular to the device, and an amount of light transmitted through the device was measured. A voltage-transmittance curve was prepared, in which the maximum amount of light corresponds to 100% transmittance and the minimum amount of light corresponds to 0% transmittance. A threshold voltage is expressed in terms of a voltage at 90% transmittance.

(11b) Threshold Voltage (Vth; Measured at 25 C.; V)

[0332] Negative dielectric anisotropy: For measurement, an LCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used. A light source was a halogen lamp. A sample was put in a normally black mode VA device in which a distance (cell gap) between two glass substrates was 4 micrometers and a rubbing direction was anti-parallel, and the device was sealed with an ultraviolet-curable adhesive. A voltage (60 Hz, rectangular waves) to be applied to the device was stepwise increased from 0 V to 20 V at an increment of 0.02 V. On the occasion, the device was irradiated with light from a direction perpendicular to the device, and an amount of light transmitted through the device was measured. A voltage-transmittance curve was prepared, in which the maximum amount of light corresponds to 100% transmittance and the minimum amount of light corresponds to 0% transmittance. A threshold voltage is expressed in terms of a voltage at 10% transmittance.

(12a) Response Time (; Measured at 25 C.; ms)

[0333] Positive dielectric anisotropy: For measurement, an LCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used. A light source was a halogen lamp. A low-pass filter was set to 5 kHz. A sample was put in a normally white mode TN device in which a distance (cell gap) between two glass substrates was 5.0 micrometers and a twist angle was 80 degrees. A voltage (rectangular waves; 60 Hz, 5 V, 0.5 second) was applied to the device. On the occasion, the device was irradiated with light from a direction perpendicular to the device, and an amount of light transmitted through the device was measured. The maximum amount of light corresponds to 100% transmittance, and the minimum amount of light corresponds to 0% transmittance. A rise time (r; millisecond) was expressed in terms of time required for a change from 90% transmittance to 10% transmittance. A fall time (f; millisecond) was expressed in terms of time required for a change from 10% transmittance to 90% transmittance. A response time was expressed by a sum of the rise time and the fall time thus determined.

(12b) Response Time (; Measured at 25 C.; ms)

[0334] Negative dielectric anisotropy: For measurement, an LCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used. A light source was a halogen lamp. A low-pass filter was set to 5 kHz. A sample was put in a normally black mode PVA device in which a distance (cell gap) between two glass substrates was 3.2 micrometers, and a rubbing direction was anti-parallel. The device was sealed with an ultraviolet-curable adhesive. The device was applied with a voltage of a little exceeding a threshold voltage for 1 minute, and then was irradiated with ultraviolet light of 23.5 mW/cm.sup.2 for 8 minutes, while applying a voltage of 5.6 V. A voltage (rectangular waves; 60 Hz, 10 V, 0.5 second) was applied to the device. On the occasion, the device was irradiated with light from a direction perpendicular to the device, and an amount of light transmitted through the device was measured. The maximum amount of light corresponds to 100% transmittance, and the minimum amount of light corresponds to 0% transmittance. A response time was expressed in terms of time required for a change from 90% transmittance to 10% transmittance (fall time; millisecond).

(13) Voltage Holding Ratio

[0335] A polymerizable compound was polymerized by irradiation with ultraviolet light by using Black Light F40T10/BL (a peak wavelength of 369 nm) made by EYE GRAPHICS CO., LTD. The device was charged by applying a pulse voltage (60 microseconds at 1 V) at 60 C. A decaying voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and area A between a voltage curve and a horizontal axis in a unit cycle was determined. Area B is an area without decay. A voltage holding ratio is expressed in terms of a percentage of area A to area B.

Raw Material

[0336] Solmix A-11 (registered trademark) is a mixture of ethanol (85.5%), methanol (13.4%) and isopropanol (1.1%), and was purchased from Japan Alcohol Trading Co., Ltd.

Synthesis Example 1

Synthesis of Compound (1-6-1)

[0337] ##STR00106##

First Step

[0338] Compound (T-1) (40.0 g), triethyl phosphonoacetate (40.7 g) and toluene (800 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Sodium ethoxide (20% ethanol solution) (61.8 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 12 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=4:1 in a volume ratio) to obtain compound (T-2) (42.0 g; 83%).

Second Step

[0339] Compound (T-2) (42.0 g), toluene (400 mL) and isopropanol (400 mL) were put in a reaction vessel, and Pd/C (0.7 g) was added thereto, and the resulting mixture was stirred under a hydrogen atmosphere at room temperature for 24 hours. The reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with brine, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=4:1 in a volume ratio) to obtain compound (T-3) (40.1 g; 95%).

Third Step

[0340] Compound (T-3) (40.1 g) and THF (400 mL) were put in a reaction vessel, and the resulting mixture was cooled to 60 C. Lithium diisopropylamide (LDA) (1.13 M; a THF solution; 142 mL) was slowly added dropwise thereto, and the resulting mixture was stirred for 1 hour. Methyl chloroformate (11.0 mL) was slowly added dropwise thereto, and the resulting mixture was stirred for 5 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water and the aqueous layer was extracted with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=4:1 in a volume ratio) to obtain compound (T-4) (30.5 g; 65%).

Fourth Step

[0341] Lithium aluminum hydride (1.7 g) and THF (300 mL) were put in a reaction vessel, and the resulting mixture was cooled with ice. A THF (600 mL) solution of compound (T-4) (30.5 g) was slowly added thereto, and the resulting mixture was stirred for 3 hours while returning to room temperature. The reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with brine, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=1:1 in a volume ratio). The resulting solution was further purified by recrystallization from heptane to obtain compound (T-5) (20.1 g; 80%).

Fifth Step

[0342] Compound (T-5) (20.1 g), triethylamine (10.3 mL) and THF (200 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Methacryloyl chloride (6.0 mL) was slowly added dropwise thereto, and the resulting mixture was stirred for 4 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=9:1 in a volume ratio) to obtain compound (1-6-1) (7.7 g; 32%).

[0343] An NMR analysis value of compound (1-6-1) obtained is as described below.

[0344] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.11 (s, 1H), 5.58 (s, 1H), 4.29-4.26 (m, 1H), 4.14-4.11 (m, 1H), 3.60-3.57 (m, 1H), 3.50-3.47 (m, 1H), 1.98-1.95 (m, 5H), 1.78-1.67 (m, 8H), 1.32-1.11 (m, 12H), 0.99-0.81 (m, 13H).

[0345] Physical properties of compound (1-6-1) were as described below.

[0346] Transition temperature: C 65.0 I.

Synthesis Example 2

[0347] Synthesis of compound (1-2-1)

##STR00107##

First Step

[0348] Paraformaldehyde (30.0 g), DABCO (56.0 g) and water (600 mL) were put in a reaction vessel, and the resulting mixture was stirred for 15 minutes at room temperature. A THF (1200 mL) solution of compound (T-6) (50.0 g) was added dropwise thereto, and the resulting mixture was stirred at room temperature for 72 hours. The reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=4:1 in a volume ratio) to obtain compound (T-7) (43.2 g; 65%).

Second Step

[0349] Compound (T-7) (42.2 g) was used as a raw material, imidazole (26.3 g) and dichloromethane (800 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. A dichloromethane (100 mL) solution of t-butyldiphenylchlorosilane (106.4 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 12 hours while returning to room temperature. The reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (heptane:ethyl acetate=10:1 in a volume ratio) to obtain compound (T-8) (107.0 g; 90%).

Third Step

[0350] Compound (T-8) (107.0 g), THF (800 mL), methanol (200 mL) and water (100 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Lithium hydroxide monohydrate (24.3 g) was added thereto, and the resulting mixture was stirred for 12 hours while returning to room temperature. The reaction mixture was poured into water, and after 6 N hydrochloric acid (100 mL) was slowly added thereto to acidify the resulting mixture, an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the resulting solution was purified by recrystallization from heptane to obtain compound (T-9) (47.4 g; 48%).

Fourth Step

[0351] Compound (1-6-1) (7.7 g), compound (T-9) (8.0 g), DMAP (1.0 g) and dichloromethane (200 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. A dichloromethane (60 mL) solution of DCC (4.8 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 12 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (heptane:ethyl acetate=19:1 in a volume ratio) to obtain compound (T-10) (9.8 g; 70%).

Fifth Step

[0352] Compound (T-10) (9.8 g) and THF (100 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. TBAF (1.00 M; a THF solution; 16.5 mL) was slowly added thereto, and the resulting mixture was stirred for 1 hour while returning to room temperature. The reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with brine, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=9:1 in a volume ratio). The resulting solution was further purified by recrystallization from heptane to obtain compound (1-2-1) (3.1 g; 47%).

[0353] An NMR analysis value of compound (1-2-1) obtained is as described below.

[0354] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.25 (s, 1H), 6.10 (s, 1H), 5.85 (s, 1H), 5.57 (s, 1H), 4.33 (d, J=4.5 Hz, 2H), 4.27-4.16 (m, 2H), 4.13-4.08 (m, 2H), 2.31 (s, 1H), 2.26-2.22 (m, 1H), 1.94 (s, 3H), 1.81-1.61 (m, 8H), 1.32-1.08 (m, 12H), 1.00-0.79 (m, 13H).

[0355] Physical properties of compound (1-2-1) were as described below.

[0356] Transition temperature: C 49.6 I.

Synthesis Example 3

[0357] Synthesis of compound (1-2-2)

##STR00108## ##STR00109##

First Step

[0358] Compound (T-11) (15.0 g), DMAP (9.33 g), Meldrum's acid (9.54 g), and dichloromethane (250 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. DCC (15.7 g) was slowly added thereto, and the resulting mixture was stirred for 12 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure. The residue and ethanol (250 mL) were put in a reaction vessel, and the resulting mixture was stirred at 70 C. After an insoluble matter was filtered off, the reaction mixture was poured into brine, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (heptane:toluene=1:1 in a volume ratio) to obtain compound (T-12) (10.2 g; 55%).

Second Step

[0359] Lithium aluminum hydride (0.6 g) and THF (100 mL) were put in a reaction vessel, and the resulting mixture was cooled with ice. A THF (100 mL) solution of compound (T-12) (10.2 g) was slowly added thereto, and the resulting mixture was stirred for 3 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with brine, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=1:1 in a volume ratio) to obtain compound (T-13) (7.35 g; 81%).

Third Step

[0360] Compound (T-13) (7.35 g), triethylamine (3.75 mL), N,N-dimethyl-4-aminopyridine (DMAP) (0.27 g) and dichloromethane (200 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Triisopropylsilyl chloride (TIPSCL) (5.05 mL) was slowly added dropwise thereto, and the resulting mixture was stirred for 24 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with brine, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=19:1 in a volume ratio) to obtain compound (T-14) (6.50 g; 60%).

Fourth Step

[0361] Compound (T-14) (6.50 g), triethylamine (3.77 mL) and THF (200 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Methacryloyl chloride (2.00 mL) was slowly added dropwise thereto, and the resulting mixture was stirred for 4 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=1:1 in a volume ratio) to obtain compound (T-15) (4.70 g; 63%).

Fifth Step

[0362] Compound (T-15) (4.70 g) and THF (100 mL) were put in a reaction vessel, and the resulting mixture was cooled at 0 C. TBAF (1.00 M; a THF solution; 10.3 mL) was slowly added thereto, and the resulting mixture was stirred for 1 hour while returning to room temperature. The reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with brine, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=9:1 in a volume ratio) to obtain compound (T-16) (1.50 g; 45%).

Sixth Step

[0363] Compound (T-17) (1.51 g; 55%) was obtained by using compound (T-16) (1.50 g) as a raw material in a manner similar to the technique in the fourth step in Synthesis Example 2.

Seventh Step

[0364] Compound (1-2-2) (0.45 g; 45%) was obtained by using compound (T-17) (1.51 g) as a raw material in a manner similar to the technique in the fifth step in Synthesis Example 2.

[0365] An NMR analysis value of compound (1-2-2) obtained is as described below.

[0366] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.25 (s, 1H), 6.09 (s, 1H), 5.82 (d, J=1.1 Hz, 1H), 5.55 (s, 1H), 5.22-5.17 (m, 1H), 4.32-4.26 (m, 3H), 4.17-4.12 (m, 3H), 2.50 (s, 1H), 2.03-1.89 (m, 5H), 1.83-1.58 (m, 9H), 1.41-1.08 (m, 11H), 0.96-0.78 (m, 13H).

[0367] Physical properties of compound (1-2-2) were as described below.

[0368] Transition temperature: C 61.2 I.

Synthesis Example 4

[0369] ##STR00110##

First Step

[0370] Compound (T-18) (20.0 g) and THF (200 mL) were put in a reaction vessel, and the resulting mixture was cooled to 70 C., and lithium diisopropylamide (LDA) (1.10 M; a THF solution; 68.0 mL) was slowly added dropwise thereto, and the resulting mixture was stirred for 1 hour. Methyl chloroformate (7.00 g) was slowly added thereto, and the resulting mixture was stirred for 4 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=9:1 in a volume ratio) to obtain compound (T-19) (19.4 g; 82%).

Second Step

[0371] Lithium aluminum hydride (1.93 g) and THF (200 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. A THF (100 mL) solution of compound (T-19) (19.4 g) was slowly added thereto, and the resulting mixture was stirred for 3 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=1:1 in a volume ratio) to obtain compound (T-20) (6.0 g; 38%).

Third Step

[0372] Compound (T-20) (6.0 g), triethylamine (3.2 mL), and THF (100 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Methacryloyl chloride (1.8 mL) was slowly added thereto, and the resulting mixture was stirred for 5 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=9:1 in a volume ratio) to obtain compound (1-9-1) (2.5 g; 34%).

[0373] An NMR analysis value of compound (1-9-1) obtained is as described below.

[0374] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.10 (s, 1H), 5.57 (d, J=1.1 Hz, 1H), 4.38 (dd, J=11.4 Hz, J=4.3 Hz, 1H), 4.23 (dd, J=11.3 Hz, J=6.7 Hz, 1H), 3.71-3.68 (m, 1H), 3.63-3.60 (m, 1H), 1.97 (s, 1H), 1.94 (s, 3H), 1.82-1.62 (m, 9H), 1.41-1.18 (m, 7H), 1.14-0.79 (m, 16H).

[0375] Physical properties of compound (1-9-1) were as described below.

[0376] Transition temperature: C 68.4 S.sub.A 89.3 I.

Synthesis Example 5

[0377] ##STR00111##

First Step

[0378] Compound (T-7), 3,4-dihydro-2H-pyran (23.3 g) and pyridinium p-toluenesulfonate (PPTS) (5.80 g) was put in a reaction vessel, and the resulting mixture was stirred at 50 C. for 10 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1 in a volume ratio) to obtain compound (T-21) (39.5 g; 80%).

Second Step

[0379] Compound (T-21) (39.5 g), THF (400 mL) and water (400 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Lithium hydroxide monohydrate (15.4 g) was added thereto, and the resulting mixture was stirred for 12 hours while returning to room temperature. The reaction mixture was poured into water, and after 6N hydrochloric acid (60 mL) was slowly added thereto to acidify the resulting mixture, an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure to obtain compound (T-22) (32.6 g; 95%).

Third Step

[0380] Compound (1-9-1) (2.0 g), compound (T-22) (1.18 g), DMAP (0.32 g), and dichloromethane (100 mL) were put in a reaction vessel, and the resulting mixture was cooled at 0 C. A dichloromethane (60 mL) solution of DCC (1.30 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 12 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=19:1 in a volume ratio) to obtain compound (T-23) (2.37 g; 82%).

Fourth Step

[0381] Compound (T-23) (2.37 g), pyridinium p-toluenesulfonate (PPTS) (0.54 g), THF (50 mL) and methanol (50 mL) were put in a reaction vessel, and the resulting mixture was stirred at 50 C. for 5 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=9:1 in a volume ratio) to obtain compound (1-9-2) (1.50 g; 75%).

[0382] An NMR analysis value of compound (1-9-2) obtained is as described below.

[0383] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.24 (s, 1H), 6.09 (s, 1H), 5.84 (s, 1H), 5.57 (s, 1H), 4.33-4.27 (m, 4H), 4.20-4.16 (m, 2H), 2.34-2.31 (m, 1H), 1.97-1.90 (m, 4H), 1.82-1.67 (m, 8H), 1.43-1.39 (m, 1H), 1.31-1.18 (m, 6H), 1.15-0.75 (m, 16H).

[0384] Physical properties of compound (1-9-2) were as described below.

[0385] Transition temperature: C 66.5 I.

Synthesis Example 6

[0386] ##STR00112##

First Step

[0387] Compound (T-24) (30.0 g), ethanol (14.4 mL), potassium phosphate (53.6 g), copper iodide (1.60 g), ethyl acetoacetate (32.8 g) and dimethyl sulfoxide (DMSO) (500 mL) were put in a reaction vessel, and the resulting mixture was stirred at 80 C. for 6 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=4:1 in a volume ratio) to obtain compound (T-25) (19.5 g; 73%).

Second Step

[0388] Compound (T-26) (16.2 g; 70%) was obtained by using compound (T-25) (19.5 g) as a raw material in a manner similar to the technique in the first step in Synthesis Example 4.

Third Step

[0389] Compound (T-27) (6.0 g; 45%) was obtained by using compound (T-26) (16.2 g) as a raw material in a manner similar to the technique in the second step in Synthesis Example 4.

Third Step

[0390] Compound (1-9-3) (2.3 g; 31%) was obtained by using compound (T-27) (6.0 g) as a raw material in a manner similar to the technique in the third step in Synthesis Example 4.

[0391] An NMR analysis value of compound (1-9-3) obtained is as described below.

[0392] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.18-7.17 (m, 4H), 6.09 (s, 1H), 5.57 (s, 1H), 4.47-4.38 (m, 2H), 3.91-3.85 (m, 2H), 3.19-3.14 (m, 1H), 2.44 (tt, J=12.2 Hz, J=3.0 Hz, 1H), 1.93-1.86 (m, 8H), 1.48-1.38 (m, 2H), 1.34-1.19 (m, 9H), 1.07-0.99 (m, 2H), 0.89 (t, J=6.8 Hz, 3H).

[0393] Physical properties of compound (1-9-3) were as described below.

[0394] Transition temperature: C 36.1 I.

Synthesis Example 7

[0395] ##STR00113##

First Step

[0396] Compound (T-28) (2.2 g; 76%) was obtained by using compound (1-9-3) (2.0 g) as a raw material in a manner similar to the technique in the third step in Synthesis Example 5.

Second Step

[0397] Compound (1-9-4) (1.3 g; 70%) was obtained by using compound (T-28) (2.2 g) as a raw material in a manner similar to the technique in the fourth step in Synthesis Example 5.

[0398] An NMR analysis value of compound (1-9-4) obtained is as follows.

[0399] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.17-7.16 (m, 4H), 6.21 (s, 1H), 6.07 (s, 1H), 5.81 (d, J=1.0 Hz, 1H), 5.55 (s, 1H), 4.46-4.39 (m, 4H), 4.27 (d, J=6.2 Hz, 2H), 3.42-3.37 (m, 1H), 2.44 (tt, J=12.2 Hz, J=3.1 Hz, 1H), 2.22-2.21 (m, 1H), 1.95 (s, 3H), 1.87-1.85 (m, 4H), 1.46-1.38 (m, 2H), 1.34-1.19 (m, 9H), 1.07-0.99 (m, 2H), 0.89 (t, J=7.0 Hz, 3H).

[0400] Physical properties of compound (1-9-4) were as described below.

[0401] Transition temperature: C 52.3 I.

Synthesis Example 8

[0402] ##STR00114##

First Step

[0403] Compound (T-29) (30.0 g), triethyl phosphonoacetate (33.0 g) and toluene (500 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Sodium ethoxide (20% ethanol solution) (50.1 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 6 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=4:1 in a volume ratio) to obtain compound (T-30) (32.8 g; 85%).

Second Step

[0404] Compound (T-30) (32.8 g), toluene (300 mL), IPA (300 mL) and Pd/C (0.55 g) were put in a reaction vessel, and the resulting mixture was stirred under a hydrogen atmosphere for 12 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=4:1 in a volume ratio). The resulting solution was further purified by recrystallization from heptane to obtain compound (T-31) (16.8 g; 51%).

Third Step

[0405] Compound (T-32) (14.1 g; 71%) was obtained by using compound (T-31) (16.8 g) as a raw material in a manner similar to the technique in the first step in Synthesis Example 4.

Fourth Step

[0406] Compound (T-33) (6.0 g; 52%) was obtained by using compound (T-32) (14.1 g) as a raw material in a manner similar to the technique in the second step in Synthesis Example 4.

Fifth Step

[0407] Compound (1-9-5) (2.3 g; 32%) was obtained by using compound (T-33) (6.0 g) as a raw material in a manner similar to the technique in the third step in Synthesis Example 4.

[0408] An NMR analysis value of compound (1-9-5) obtained is as described below.

[0409] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.14-7.10 (m, 4H), 6.12 (s, 1H), 5.59 (s, 1H), 4.43-4.40 (m, 1H), 4.28-4.25 (m, 1H), 3.75-3.64 (m, 2H), 2.55 (t, J=7.6 Hz, 2H), 2.47-2.42 (m, 1H), 2.14 (s, 1H), 1.96-1.91 (m, 7H), 1.74-1.69 (m, 1H), 1.62-1.22 (m, 11H), 0.88 (t, J=6.8 Hz, 3H).

[0410] Physical properties of compound (1-9-5) were as described below.

[0411] Transition temperature: C<50.0 I.

Synthesis Example 9

[0412] ##STR00115##

First Step

[0413] Compound (T-34) (1.9 g; 68%) was obtained by compound (1-9-5) (2.0 g) as a raw material according to the third step in Synthesis Example 5.

Second Step

[0414] Compound (1-9-6) (1.2 g; 75%) was obtained by using compound (T-34) (1.9 g) as a raw material according to the fourth step in Synthesis Example 5.

[0415] An NMR analysis value of compound (1-9-6) obtained is as described below.

[0416] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.13-7.10 (m, 4H), 6.27 (s, 1H), 6.11 (s, 1H), 5.86 (s, 1H), 5.58 (s, 1H), 4.40-4.32 (m, 4H), 4.25-4.20 (m, 2H), 2.56 (t, J=7.6 Hz, 2H), 2.45 (tt, J=12.1 Hz, J=2.9 Hz, 1H), 2.35-2.32 (m, 1H), 2.04-1.91 (m, 7H), 1.62-1.26 (m, 12H), 0.88 (t, J=6.8 Hz, 3H).

[0417] Physical properties of compound (1-9-6) were as described below.

[0418] Transition temperature: C 35.8 I.

Synthesis Example 10

[0419] ##STR00116##

First Step

[0420] In a reaction vessel, 2-(1,3-dioxane-2-yl)ethyltriphenylphosphonium bromide (103.7 g) and THF (500 mL) were put, and the resulting mixture was cooled to 30 C., and potassium t-butoxide (25.4 g) was added thereto, and the resulting mixture was stirred for 1 hour. A THF (300 mL) solution of compound (T-35) (50.0 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 6 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=1:1 in a volume ratio) to obtain compound (T-36) (63.0 g; 92%).

Second Step

[0421] Compound (T-36) (63.0 g), toluene (500 mL), IPA (500 mL) and Pd/C (0.55 g) were put in a reaction vessel, and the resulting mixture was stirred under a hydrogen atmosphere for 16 hours. After an insoluble matter was filtered out, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=1:1 in a volume ratio) to obtain compound (T-37) (60.1 g; 95%).

Third Step

[0422] Compound (T-37) (60.1 g), formic acid (75.8 g) and toluene (1,000 mL) were put in a reaction vessel, and the resulting mixture was stirred at 100 C. for 6 hours. After an insoluble matter was filtered off, the resulting solution was neutralized with a sodium hydrogencarbonate aqueous solution, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography with toluene to obtain compound (T-38) (45.0 g; 89%).

Fourth Step

[0423] Compound (T-38) (45.0 g), potassium peroxymonosulfate (OXONE) (108.3 g) and DMF (1,000 mL) were put in a reaction vessel, and the resulting mixture was stirred at room temperature for 8 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure to obtain compound (T-39) (28.5 g; 60%).

Fifth Step

[0424] Compound (T-39) (28.5 g), sulfuric acid (0.5 mL) and methanol (500 mL) were put in a reaction vessel, and the resulting mixture was stirred at 60 C. for 5 hours. After an insoluble matter was filtered off, the resulting solution was concentrated, and the residue was purified by silica gel chromatography with toluene to obtain compound (T-40) (22.3 g; 75%).

Sixth Step

[0425] Compound (T-41) (18.3 g; 70%) was obtained by using compound (T-40) (22.3 g) as a raw material in a manner similar to the technique in the first step in Synthesis Example 4.

Seventh Step

[0426] Compound (T-42) (5.9 g; 38%) was obtained by using compound (T-41) (18.3 g) as a raw material in a manner similar to the technique in the second step in Synthesis Example 4.

Eighth Step

[0427] Compound (1-9-7) (2.4 g; 34%) was obtained by using compound (T-42) (5.9 g) as a raw material in a manner similar to the technique in the third step in Synthesis Example 4.

[0428] An NMR analysis value of compound (1-9-7) obtained is as described below.

[0429] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.11 (s, 1H), 5.81 (s, 1H), 4.31-4.28 (m, 1H), 4.17-4.14 (m, 1H), 3.63-3.58 (m, 1H), 3.54-3.49 (m, 1H), 1.98-1.95 (m, 4H), 1.84-1.69 (m, 9H), 1.41-1.18 (m, 10H), 1.15-1.06 (m, 4H), 1.02-0.80 (m, 13H).

[0430] Physical properties of compound (1-9-7) were as described below.

[0431] Transition temperature: C 33.6 S.sub.A 101 I.

Synthesis Example 11

[0432] ##STR00117##

First Step

[0433] Compound (T-43) (2.1 g; 74%) was obtained by using compound (1-9-7) (2.0 g) as a raw material in a manner similar to the technique in the third step in Synthesis Example 5.

Second Step

[0434] Compound (1-9-8) (1.3 g; 72%) was obtained by using compound (T-43) (2.1 g) as a raw material in a manner similar to the technique in the fourth step in Synthesis Example 5.

[0435] An NMR analysis value of compound (1-9-8) obtained is as described below.

[0436] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.25 (s, 1H), 6.10 (s, 1H), 5.85 (d, J=1.1 Hz, 1H), 5.57 (s, 1H), 4.33 (d, J=6.5 Hz, 2H), 4.24-4.11 (m, 4H), 2.28 (t, J=6.6 Hz, 1H), 2.09-2.03 (m, 1H), 1.94 (s, 3H), 1.75-1.67 (m, 8H), 1.44-1.39 (m, 2H), 1.32-1.18 (m, 8H), 1.15-1.06 (m, 4H), 1.02-0.79 (m, 13H).

[0437] Physical properties of compound (1-9-8) were as described below.

[0438] Transition temperature: C 71.4 I.

Synthesis Example 12

[0439] ##STR00118##

First Step

[0440] Compound (T-20) (2.0 g), compound (T-22) (2.63 g), DMAP (0.78 g) and dichloromethane (100 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. A dichloromethane (60 mL) solution of DCC (2.92 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 12 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=9:1 in a volume ratio) to obtain compound (T-44) (2.83 g; 68%).

Second Step

[0441] Compound (T-44) (2.83 g), pyridinium p-toluenesulfonate (PPTS) (1.09 g), THF (50 mL) and methanol (50 mL) were put in a reaction vessel, and the resulting mixture was stirred at 50 C. for 8 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=1:1 in a volume ratio) to obtain compound (1-10-1) (1.47 g; 70%).

[0442] An NMR analysis value of compound (1-10-1) obtained is as described below.

[0443] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.24 (s, 2H), 5.82 (s, 2H), 4.35-4.31 (m, 6H), 4.22-4.19 (m, 2H), 2.36 (s, 2H), 1.97-1.91 (s, 1H), 1.82-1.63 (m, 8H), 1.43-1.18 (m, 7H), 1.15-0.79 (m, 16H).

[0444] Physical properties of compound (1-10-1) were as described below.

[0445] Transition temperature: C 102 I.

Synthesis Example 13

[0446] ##STR00119##

First Step

[0447] Compound (T-45) (2.7 g; 64%) was obtained by using compound (T-27) (2.0 g) as a raw material in a manner similar to the technique in the first step in Synthesis Example 12.

Second Step

[0448] Compound (1-10-2) (1.3 g; 65%) was obtained by using compound (T-45) (2.7 g) as a raw material in a manner similar to the technique in the second step in Synthesis Example 12.

[0449] An NMR analysis value of compound (1-10-2) obtained is as described below.

[0450] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.20-7.16 (m, 4H), 6.26 (s, 2H), 5.83 (d, J=0.8 Hz, 2H), 4.46 (d, J=6.6 Hz, 4H), 4.28 (d, J=6.3 Hz, 4H), 3.44-3.39 (m, 1H), 2.44 (tt, J=12.2 Hz, J=3.1 Hz, 1H), 2.16-2.13 (m, 2H), 1.87-1.85 (m, 4H), 1.46-1.19 (m, 11H), 1.07-0.99 (m, 2H), 0.89 (t, J=6.8 Hz, 3H).

[0451] Physical properties of compound (1-10-2) were as described below.

[0452] Transition temperature: C 65.8 I.

Synthesis Example 14

[0453] ##STR00120##

First Step

[0454] Compound (T-46) (2.5 g; 59%) was obtained by using compound (T-33) (2.0 g) as a raw material according to the first step in Synthesis Example 12.

Second Step

[0455] Compound (1-10-3) (1.1 g; 60%) was obtained by using compound compound (T-46) (2.7 g) as a raw material in a manner similar to the technique in the second step in Synthesis Example 12.

[0456] An NMR analysis value of compound (1-10-3) obtained is as described below.

[0457] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.14-7.10 (m, 4H), 6.27 (s, 2H), 5.87 (d, J=1.1 Hz, 2H), 4.39-4.33 (m, 6H), 4.27-4.20 (m, 2H), 2.57-2.54 (m, 2H), 2.45 (tt, J=12.2 Hz, J=3.1 Hz, 1H), 2.38-2.35 (m, 2H), 2.05-1.91 (m, 5H), 1.63-1.1.26 (m, 11H), 0.88 (t, J=6.8 Hz, 3H).

[0458] Physical properties of compound (1-10-3) were as described below.

[0459] Transition temperature: C 65.6 I.

Synthesis Example 15

[0460] ##STR00121##

First Step

[0461] Compound (T-47) (2.7 g; 67%) was obtained by using compound (T-head-42) (2.0 g) as a raw material in a manner similar to the technique in the first step in Synthesis Example 12.

Second Step

[0462] Compound (1-10-4) (1.3 g; 64%) was obtained by using compound (T-47) (2.7 g) as a raw material in a manner similar to the technique in the second step in Synthesis Example 12.

[0463] An NMR analysis value of compound (1-10-4) obtained is as described below.

[0464] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.25 (s, 2H), 5.85 (d, J=1.1 Hz, 2H), 4.33 (d, J=6.3 Hz, 4H), 4.25-4.22 (m, 2H), 4.18-4.14 (m, 2H), 2.30-2.28 (m, 2H), 2.11-2.06 (m, 1H), 1.75-1.67 (m, 8H), 1.44-1.39 (m, 2H), 1.32-0.79 (m, 25H).

[0465] Physical properties of compound (1-10-4) were as described below.

[0466] Transition temperature: C 85.7 S.sub.A 125 I.

Synthesis Example 16

[0467] ##STR00122## ##STR00123##

First Step

[0468] Compound (T-24) (50.0 g) and THF (1,000 mL) were put in a reaction vessel, and the resulting mixture was cooled to 70 C. Isopropylmagnesium chloride-lithium chloride (1.3 M; a THF solution; 130.0 mL) was slowly added dropwise thereto, and the resulting mixture was stirred for 1 hour. DMF (13.0 mL) was added dropwise thereto, and the resulting mixture was stirred for 4 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=4:1 in a volume ratio) to obtain compound (T-48) (34.5 g; 95%).

Second Step

[0469] Methoxymethyl triphenylphosphonium chloride (54.9 g) and THF (1,000 mL) were put in a reaction vessel, and the resulting mixture was cooled to 30 C. Potassium t-butoxide (18.0 g) was added thereto, and the resulting mixture was stirred for 1 hour. A THF (500 mL) solution of compound (T-48) (34.5 g) was added dropwise thereto, and the resulting mixture was stirred for 5 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=1:4 in a volume ratio) to obtain compound (T-49) (31.7 g; 83%).

Third Step

[0470] Compound (T-49) (31.7 g), formic acid (50.9 g) and toluene (1,000 mL) were put in a reaction vessel, and the resulting mixture was stirred at 100 C. for 6 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and the resulting solution was neutralized with sodium hydrogencarbonate water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=4:1 in a volume ratio) to obtain compound (T-50) (26.5 g; 88%).

Fourth Step

[0471] Compound (T-50) (26.5 g), triethyl phosphonoacetate (26.2 g), toluene (500 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Sodium ethoxide (a 20% ethanol solution) (39.7 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 6 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=9:1 in a volume ratio) to obtain compound (T-51) (30.6 g; 92%).

Fifth Step

[0472] Compound (T-51) (30.6 g), Pd/C (0.55 g), toluene (250 mL) and IPA (250 mL) were put in a reaction vessel, and the resulting mixture was stirred under a hydrogen atmosphere for 12 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=9:1 in a volume ratio) to obtain compound (T-52) (29.2 g; 95%).

Sixth Step

[0473] Compound (T-52) (29.2 g) and THF (250 mL) were put in a reaction vessel, and the resulting mixture was cooled to 70 C. Lithium diisopropylamide (LDA) (1.1M; a THF solution; 92.5 mL) was slowly added dropwise thereto. The resulting mixture was stirred for 1 hour, and benzyl chloromethyl ether (16.0 g) was added dropwise thereto, and the resulting mixture was stirred for 12 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=9:1 in a volume ratio) to obtain compound (T-53) (31.5 g; 80%).

Seventh Step

[0474] Compound (T-53) (31.5 g), palladium hydroxide (0.28 g), toluene (250 mL) and IPA (250 mL) were put in a reaction vessel, and the resulting mixture was stirred under a hydrogen atmosphere for 12 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=4:1 in a volume ratio) to obtain compound (T-54) (23.3 g; 92%).

Eighth Step

[0475] Compound (T-54) (23.3 g), 3,4-dihydro-2H-pyran (5.8 g), pyridinium p-toluenesulfonate (PPTS) (1.5 g) and dichloromethane (500 mL) were put in a reaction vessel, and were stirred at room temperature for 8 hours. The reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=9:1 in a volume ratio) to obtain compound (T-55) (25.4 g; 89%).

Ninth Step

[0476] Lithium aluminum hydride (LAH) (1.2 g) and THF (300 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. A THF (100 mL) solution of compound (T-55) (25.4 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 3 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=4:1 in a volume ratio) to obtain compound (T-56) (19.2 g; 83%).

Tenth Step

[0477] Compound (T-56) (19.2 g), triethylamine (7.6 mL), and THF (200 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Methacryloyl chloride (5.3 mL) was slowly added thereto, and the resulting mixture was stirred for 5 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=19:1 in a volume ratio) to obtain compound (T-57) (17.9 g; 80%).

Eleventh Step

[0478] Compound (T-57) (17.9 g), pyridinium p-toluenesulfonate (PPTS) (4.6 g), THF (200 mL) and methanol (200 mL) were put in a reaction vessel, and the resulting mixture was stirred at 50 C. for 6 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=9:1 in a volume ratio) to obtain compound (1-9-11) (12.4 g; 84%).

[0479] An NMR analysis value of compound (1-9-11) obtained is as described below.

[0480] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.13-7.09 (m, 4H), 6.10 (s, 1H), 5.57 (s, 1H), 4.33-4.30 (m, 1H), 4.23-4.20 (m, 1H), 3.65-3.62 (m, 1H), 3.58-3.54 (m, 1H), 2.66 (t, J=8.0 Hz, 2H), 2.45-2.39 (m, 1H), 1.94-1.81 (m, 8H), 1.74-1.60 (m, 2H), 1.46-1.19 (m, 12H), 1.07-0.99 (m, 2H), 0.89 (t, J=6.9 Hz, 3H).

[0481] Physical properties of compound (1-9-11) were as described below.

[0482] Transition temperature: C 24.7 I.

Synthesis Example 17

[0483] ##STR00124##

First Step

[0484] Compound (T-58) (2.1 g; 74%) was obtained by using compound (1-9-11) (2.0 g) as a raw material in a manner similar to the technique in the third step in Synthesis Example 5.

Second Step

[0485] Compound (1-9-12) (1.4 g; 78%) was obtained by using compound (T-58) (2.1 g) as a raw material in a manner similar to the technique in the fourth step in Synthesis Example 5.

[0486] An NMR analysis value of compound (1-9-12) obtained is as described below.

[0487] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.14-7.08 (m, 4H), 6.24 (s, 1H), 6.10 (s, 1H), 5.85 (s, 1H), 5.57 (s, 1H), 4.32 (d, J=6.1 Hz, 2H), 4.27-4.18 (m, 4H), 2.67 (t, J=7.4 Hz, 2H), 2.45-2.40 (m, 2H), 2.18-2.12 (m, 1H), 1.93 (s, 3H), 1.88-1.84 (m, 4H), 1.77-1.72 (m, 2H), 1.46-1.38 (m, 2H), 1.34-1.19 (m, 9H), 1.07-0.99 (m, 2H), 0.89 (t, J=6.8 Hz, 3H).

[0488] Physical properties of compound (1-9-12) were as described below.

[0489] Transition temperature: C 30.2 S.sub.A-26.3 I.

Synthesis Example 18

[0490] ##STR00125## ##STR00126##

First Step

[0491] Methoxymethyl triphenylphosphonium chloride (84.2 g) and THF (1,000 mL) were put in a reaction vessel, and the resulting mixture was cooled to 30 C. Potassium t-butoxide (27.6 g) was added thereto, and the resulting mixture was stirred for 1 hour. A THF (500 mL) solution of compound (T-29) (50.0 g) was added dropwise thereto, and the resulting mixture was stirred for 5 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=1:4 in a volume ratio) to obtain compound (T-59) (46.3 g; 83%).

Second Step

[0492] Compound (T-59) (46.3 g), p-toluenesulfonic acid (PTSA) (3.2 g), and toluene (1,000 mL) were put in a reaction vessel, and the resulting mixture was stirred at 100 C. for 12 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=1:1 in a volume ratio) to obtain compound (T-60) (49.2 g; 95%).

Third Step

[0493] Compound (T-60) (49.2 g), formic acid (74.4 g) and toluene (1,000 mL) were put in a reaction vessel, and the resulting mixture was stirred at room temperature for 8 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and the resulting solution was neutralized with sodium hydrogencarbonate water. An aqueous layer was subjected to extraction with toluene, and Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=1:1 in a volume ratio) to obtain compound (T-61) (35.0 g; 84%).

Fourth Step

[0494] Methoxymethyl triphenylphosphonium chloride (55.7 g) and THF (1,000 mL) were put in a reaction vessel, and the resulting mixture was cooled to 30 C. Potassium t-butoxide (18.2 g) was added thereto, and the resulting mixture was stirred for 1 hour. A THF (500 mL) solution of compound (T-61) (35.0 g) was added dropwise thereto, and the resulting mixture was stirred for 5 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=1:4 in a volume ratio) to obtain compound (T-62) (36.5 g; 94%).

Fifth Step

[0495] Compound (T-62) (36.5 g), formic acid (58.6 g) and toluene (1,000 mL) were put in a reaction vessel, and the resulting mixture was stirred at 100 C. for 4 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and the resulting solution was neutralized with sodium hydrogencarbonate water. An aqueous layer was subjected to extraction with toluene, and organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=1:1 in a volume ratio) to obtain compound (T-63) (33.0 g; 95%).

Sixth Step

[0496] Compound (T-64) (38.2 g; 92%) was obtained by using compound (T-63) (33.0 g) as a raw material in a manner similar to the technique in the fourth step in Synthesis Example 16.

Seventh Step

[0497] Compound (T-65) (18.7 g; 48%) was obtained by using compound (T-64) (38.2 g) as a raw material in a manner similar to the technique in the fifth step in Synthesis Example 16.

Eighth Step

[0498] Compound (T-66) (21.5 g; 85%) was obtained by using compound (T-65) (18.7 g) as a raw material in a manner similar to the technique in the sixth step in Synthesis Example 16.

Ninth Step

[0499] Compound (T-67) (15.6 g; 90%) was obtained by using compound (T-66) (21.5 g) as a raw material in a manner similar to the technique in the seventh step in Synthesis Example 16.

Tenth Step

[0500] Compound (T-68) (16.8 g; 88%) was obtained by using compound (T-67) (15.6 g) as a raw material in a manner similar to the technique in the eighth step in Synthesis Example 16.

Tenth Step

[0501] Compound (T-69) (13.0 g; 85%) was obtained by using compound (T-68) (16.8 g) as a raw material in a manner similar to the technique in the ninth step in Synthesis Example 16.

Eleventh Step

[0502] Compound (T-70) (11.6 g; 77%) was obtained by using compound (T-69) (13.0 g) as a raw material in a manner similar to the technique in the tenth step in Synthesis Example 16.

Twelfth Step

[0503] Compound (1-9-9) (7.8 g; 82%) was obtained by using compound (T-70) (11.6 g) as a raw material in a manner similar to the technique in the eleventh step in Synthesis Example 16.

[0504] An NMR analysis value of compound (1-9-9) obtained is as described below.

[0505] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.11-7.08 (m, 4H), 6.11 (s, 1H), 5.57 (s, 1H), 4.31-4.28 (m, 1H), 4.19-4.16 (m, 1H), 3.63-3.60 (m, 1H), 3.55-3.52 (m, 1H), 1.95 (s, 3H), 1.89-1.81 (m, 5H), 1.62-1.56 (m, 2H), 1.47-1.28 (m, 12H), 1.09-1.01 (m, 2H), 0.88 (t, J=6.7 Hz, 3H).

[0506] Physical properties of compound (1-9-9) were as described below.

[0507] Transition temperature: C<50 I.

Synthesis Example 19

[0508] ##STR00127##

First Step

[0509] Compound (T-71) (3.2 g; 75%) was obtained by using compound (1-9-9) (3.0 g) as a raw material in a manner similar to the technique in the third step in Synthesis Example 5.

Second Step

[0510] Compound (1-9-10) (1.9 g; 70%) was obtained by using compound (T-71) (3.2 g) as a raw material in a manner similar to the technique in the fourth step in Synthesis Example 5.

[0511] An NMR analysis value of compound (1-9-10) obtained is as described below.

[0512] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.12-7.08 (m, 4H), 6.26 (s, 1H), 6.11 (s, 1H), 5.86 (s, 1H), 5.58 (s, 1H), 4.34 (d, J=6.5 Hz, 2H), 4.26-4.14 (m, 4H), 2.55 (t, J=7.8 Hz, 2H), 2.45-2.40 (m, 1H), 2.34 (s, 1H), 2.13-2.08 (m, 1H), 1.95 (s, 3H), 1.90-1.84 (m, 4H), 1.63-1.56 (m, 2H), 1.48-1.39 (m, 4H), 1.35-1.27 (m, 7H), 1.09-1.01 (m, 2H), 0.88 (t, J=6.8 Hz, 3H).

[0513] Physical properties of compound (1-9-10) were as described below.

[0514] Transition temperature: C 35.9 I.

Synthesis Example 20

[0515] ##STR00128##

First Step

[0516] Compound (T-73) (31.8 g; 70%) was obtained by using compound (T-72) (50.0 g) as a raw material in a manner similar to the technique in the first step in Synthesis Example 6.

Second Step

[0517] Compound (T-74) (26.2 g; 72%) was obtained by using compound (T-73) (31.8 g) as a raw material in a manner similar to the technique in the second step in Synthesis Example 6.

Third Step

[0518] Compound (T-75) (10.1 g; 46%) was obtained by using compound (T-74) (26.2 g) as a raw material in a manner similar to the technique in the third step in Synthesis Example 6.

Fourth Step

[0519] Compound (1-9-41) (3.8 g; 32%) was obtained by using compound (T-75) (10.1 g) as a raw material in a manner similar to the technique in the fourth step in Synthesis Example 6.

[0520] An NMR analysis value of compound (1-9-41) obtained is as described below.

[0521] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.18-7.16 (m, 4H), 6.09 (s, 1H), 5.57 (s, 1H), 4.47-4.38 (m, 2H), 3.91-3.83 (m, 2H), 3.20-3.14 (m, 1H), 2.45-2.40 (m, 1H), 1.97-1.72 (m, 12H), 1.42-0.82 (m, 22H).

[0522] Physical properties of compound (1-9-41) were as described below.

[0523] Transition temperature: C 46.3 I.

##STR00129##

Synthesis Example 21

First Step

[0524] Compound (T-76) (3.1 g; 75%) was obtained by using compound (1-9-41) (3.0 g) as a raw material in a manner similar to the technique in the third step in Synthesis Example 5.

Second Step

[0525] Compound (1-9-42) (1.9 g; 71%) was obtained by using compound (T-76) (3.1 g) as a raw material in a manner similar to the technique in the fourth step in Synthesis Example 5.

[0526] An NMR analysis value of compound (1-9-42) obtained is as described below.

[0527] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.17 (s, 4H), 6.21 (s, 1H), 6.07 (s, 1H), 5.80 (s, 1H), 5.56 (s, 1H), 4.46-4.39 (m, 4H), 4.27 (d, J=6.6 Hz, 2H), 3.42-3.37 (m, 1H), 2.45-2.39 (m, 1H), 2.12 (t, J=6.6 Hz, 1H), 1.91-1.72 (m, 11H), 1.46-0.95 (m, 16H), 0.89-0.82 (m, 5H).

[0528] Physical properties of compound (1-9-42) were as described below.

[0529] Transition temperature: C 80.0 I.

Synthesis Example 22

[0530] ##STR00130## ##STR00131##

First Step

[0531] Compound (T-77) (50.0 g), triethyl phosphonoacetate (48.3 g) and toluene (500 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Sodium ethoxide (20% ethanol solution) (73.3 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 6 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=9:1 in a volume ratio) to obtain compound (T-78) (60.7 g; 97%).

Second Step

[0532] Compound (T-78) (60.7 g), Pd/C (0.51 g), toluene (500 mL) and IPA (50 mL) were put in a reaction vessel, and the resulting mixture was stirred under a hydrogen atmosphere for 12 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with toluene. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:heptane=9:1 in a volume ratio), and the resulting solution was further purified by recrystallization from Solmix to obtain compound (T-79) (33.6 g; 55%).

Third Step

[0533] Compound (T-80) (38.8 g; 86%) was obtained by using compound (T-79) (33.6 g) as a raw material in a manner similar to the technique in the sixth step in Synthesis Example 16.

Fourth Step

[0534] Compound (T-81) (29.8 g; 95%) was obtained by using compound (T-80) (38.8 g) as a raw material in a manner similar to the technique in the seventh step in Synthesis Example 16.

Fifth Step

[0535] Compound (T-82) (34.6 g; 95%) was obtained by using compound (T-81) (29.8 g) as a raw material in a manner similar to the technique in the eighth step in Synthesis Example 16.

Sixth Step

[0536] Compound (T-83) (30.5 g; 97%) was obtained by using compound (T-82) (34.6 g) as a raw material in a manner similar to the technique in the ninth step in Synthesis Example 16.

Seventh Step

[0537] Compound (T-84) (26.6 g; 75%) was obtained by using compound (T-83) (30.5 g) as a raw material in a manner similar to the technique in the tenth step in Synthesis Example 16.

Eighth Step

[0538] Compound (1-9-51) (18.3 g; 83%) was obtained by using compound (T-84) (26.6 g) as a raw material according to the eleventh step in Synthesis Example 16.

[0539] An NMR analysis value of compound (1-9-51) obtained is as described below.

[0540] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.10 (s, 1H), 5.57 (s, 1H), 4.40-4.37 (m, 1H), 4.24-4.20 (m, 1H), 3.69-3.61 (m, 2H), 1.9-1.94 (m, 4H), 1.78-1.58 (m, 9H), 1.43-1.37 (m, 1H), 1.32-1.02 (m, 17H), 0.90-0.79 (m, 9H).

[0541] Physical properties of compound (1-9-51) were as described below.

[0542] Transition temperature: C 54.5 S.sub.A 81.0 I.

Synthesis Example 23

[0543] ##STR00132##

First Step

[0544] Compound (T-85) (3.3 g; 78%) was obtained byusing compound (1-9-51) (3.0 g) as a raw material in a manner similar to the technique in the third step in Synthesis Example 5.

Second Step

[0545] Compound (1-9-52) (2.1 g; 75%) was obtained by using compound (T-85) (3.3 g) as a raw material in a manner similar to the technique in the fourth step in Synthesis Example 5.

[0546] An NMR analysis value of compound (1-9-52) obtained is as described below.

[0547] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.24 (s, 1H), 6.09 (s, 1H), 5.84 (s, 1H), 5.56 (s, 1H), 4.33-4.28 (m, 4H), 4.20-4.16 (m, 2H), 2.28 (t, J=6.6 Hz, 1H), 1.97-1.91 (m, 4H), 1.79-1.69 (m, 8H), 1.47-1.41 (m, 1H), 1.32-1.07 (m, 17H), 0.90-0.82 (m, 9H).

[0548] Physical properties of compound (1-9-52) were as described below.

[0549] Transition temperature: C 64.0 I.

Synthesis Example 24

[0550] ##STR00133##

First Step

[0551] Compound (T-86) (50.0 g), paraformaldehyde (31.7 g), dicyclohexylamine (95.7 mL) and methanol (500 mL) were put in a reaction vessel, and the resulting mixture was stirred at 65 C. for 5 hours. After the reaction mixture was concentrated under reduced pressure, the resulting mixture was poured into water, and an aqueous layer was washed with t-butyl methyl ether. Then, 3N hydrochloric acid (200 mL) was added to the aqueous layer, and precipitated salt was removed by filtration. An aqueous layer obtained was subjected to extraction with ethyl acetate, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and purified by distillation to obtain compound (T-87) (40.4 g; 72%).

Second Step

[0552] Compound (T-20) (8.00 g), compound (T-87) (3.29 g) and dichloromethane (320 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. Thereto, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (5.43 g) and triethylamine (6.1 mL) were added, and the resulting mixture was stirred for 12 hours while returning to room temperature. The reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=3:1 in a volume ratio) to obtain compound (T-88) (4.72 g; 40%).

Third Step

[0553] Compound (T-88) (4.72 g), compound (T-22) (2.58 g), DMAP (0.71 g) and dichloromethane (75 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0 C. A dichloromethane (20 mL) solution of DCC (3.58 g) was slowly added dropwise thereto, and the resulting mixture was stirred for 12 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=10:1 in a volume ratio) to obtain compound (T-89) (6.50 g; 98%).

Fourth Step

[0554] Compound (T-89) (6.50 g), pyridinium p-toluenesulfonate (PPTS) (1.41 g), THF (50 mL) and methanol (50 mL) were put in a reaction vessel, and the resulting mixture was stirred at 50 C. for 4 hours. The reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. Organic layers combined were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=3:1 in a volume ratio), and the resulting solution was further purified by recrystallization from heptane to obtain compound (1-9-54) (4.69 g; 85%).

[0555] An NMR analysis value of compound (1-9-54) obtained is as described below.

[0556] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 6.30 (s, 1H), 6.25 (s, 1H), 5.86 (d, J=1.4 Hz, 1H), 5.85 (s, 1H), 4.38-4.29 (m, 4H), 4.24-4.16 (m, 2H), 4.12 (s, 2H), 3.40 (s, 3H), 2.34-2.29 (m, 1H), 1.97-1.90 (m, 1H), 1.85-1.64 (m, 8H), 1.47-1.38 (m, 1H), 1.33-1.18 (m, 6H), 1.18-0.78 (m, 16H).

[0557] Physical properties of compound (1-9-54) were as follows.

[0558] Transition temperature: C 37.3 I.

Comparative Example 1

[0559] As a comparative compound, compound (S-1) was prepared, and characteristics were measured. The compound was selected because the compound is described in WO 2014/090362 A, and is similar to the compound of the invention.

##STR00134##

[0560] An NMR analysis value of comparative compound (S-1) was as described below.

[0561] .sup.1H-NMR: Chemical shifts (ppm; CDCl.sub.3): 7.57-7.52 (m, 2H), 7.45-7.42 (m, 2H), 7.36-7.30 (m, 1H), 7.04-6.95 (m, 2H), 4.75 (d, 6.0 Hz, 2H), 2.62 (t, J=7.8 Hz, 2H), 1.75-1.64 (m, 3H), 0.98 (t, J=7.4 Hz, 3H).

[0562] Vertical alignability and voltage holding ratios of compound (No. 1-2-1) and compound (No. 1-6-1) and comparative compound (S-1) were compared. In addition, for evaluation, composition (i) and polymerizable compound (RM-1) were used.

[0563] A proportion of components of composition (i) is expressed in terms of weight percent (% by weight).

##STR00135##

[0564] Polymerizable compound (RM-1) is shown below.

##STR00136##

Vertical Alignability

[0565] Polymerizable compound (RM-1) was added to composition (i) in a proportion of 0.4% by weight. Compound (1-2-1), compound (1-6-1) or comparative compound (S-1) was added thereto in a proportion of 3.0% by weight. The resulting mixture was injected into a device having no alignment film in which a distance (cell gap) between two glass substrates was 3.5 micrometers. The polymerizable compound was polymerized by irradiation with ultraviolet light (20J) by using Black Light F40T10/BL (peak wavelength: 369 nm) made by EYE GRAPHICS CO., LTD. The device was charged by applying a pulse voltage (60 microseconds at 1 V) at 60 C. A decaying voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and area A between a voltage curve and a horizontal axis in a unit cycle was determined. Area B is an area without decay. The voltage holding ratio is expressed in terms of a percentage of area A to area B. The device was set to the polarizing microscope, and the device was irradiated with light from below, and presence or absence of light leakage was observed. When liquid crystal molecules were sufficiently aligned and no light passed through the device, vertical alignability was determined as good. When light passing through the device was observed, vertical alignability was expressed as poor.

TABLE-US-00002 TABLE 2 Physical properties of compound (1-2-1), compound (1-6-1) and comparative compound (S-1) [00137] [00138] [00139] Vertical Good Good Good alignability Voltage 83.1% 86.6% 29.6% holding ratio (VHR)

[0566] Physical properties of compound (1-2-1) in Synthesis Example 1, compound (1-6-1) and comparative compound (S-1) are summarized in Table 2. Both the compounds exhibited good vertical alignability in the device having no alignment film. Meanwhile, when compound (1-2-1) and compound (1-6-1) were used, the voltage holding ratio is higher in comparison with the case of using comparative compound (S-1). The reason is that, while the polar compound having such an OH group as in comparative compound (S-1) significantly reduces the voltage holding ratio of the device, reduction of the voltage holding ratio is suppressed by incorporation of the polar compound into the polymer formed by the polymerizable compound by providing the polar compound with polymerizability as in compound (1-2-1) and compound (1-6-1). Accordingly, compound (1-2-1) and compound (1-6-1) are reasonably a superb compound that exhibits good vertical alignability without reducing the voltage holding ratio of the device.

Comparative Example 2

Vertical Alignability

[0567] Polymerizable compound (RM-1) was added to composition (i) in a proportion of 0.4% by weight. Compound (1-1-2), compound (1-6-1) or comparative compound (S-1) was added thereto in a proportion of 0.3% by weight to 5.0% by weight. The resulting mixture was injected into a device having no alignment film, in which a distance (cell gap) between two glass substrates was 3.5 micrometers. The polymerizable compound was polymerized by irradiation (20J) with ultraviolet light by using Black Light F40T10/BL (peak wavelength: 369 nm) made by EYE GRAPHICS CO., LTD. The device was set to a polarizing microscope, and the device was irradiated with light from below, and presence or absence of light leakage was observed. When liquid crystal molecules were sufficiently aligned and no light passed through the device, vertical alignability was determined as good. When light passing through the device was observed, vertical alignability was expressed as poor.

TABLE-US-00003 TABLE 3 Physical properties of compound (1-10-1) and comparative compound (S-1) Addition concentration (% by weight) [00140] [00141] 0.30% Good Poor 0.50% Good Poor 1% Good Poor 3% Good Good 5% Good Good

[0568] Physical properties of the compound (1-10-1) in Synthesis Example 12 and comparative compound (S-1) are summarized in Table 3. While good vertical alignability was not confirmed unless comparative compound (S-1) was added to the liquid crystal composition in a proportion of 3% by weight or more, good vertical alignability was confirmed when compound (1-10-1) was added to the liquid crystal composition in a proportion of 0.3% by weight or more. Accordingly, compound (1-10-1) is reasonably a superb compound that vertically aligns at a concentration lower than the concentration of comparative compound (S-1).

[0569] According to the synthesis method described in Example 1, compounds (1-1-1) to (1-1-20), compounds (1-2-1) to (1-2-200), compounds (1-3-1) to (1-3-140), compounds (1-4-1) to (1-4-134), (1-5-1) to (1-5-20), compounds (1-6-1) to (1-6-180), compounds (1-7-1) to (1-7-140), compounds (1-8-1) to (1-8-134), compounds (1-9-1) to (1-9-80), compounds (1-10-1) to (1-10-180), compound (1-11-1) to (1-11-140) and compounds (1-12-1) to (1-12-220) described below can be prepared.

##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177##

##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223##

##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250##

##STR00251## ##STR00252## ##STR00253## ##STR00254## ##STR00255## ##STR00256## ##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261## ##STR00262## ##STR00263## ##STR00264## ##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271## ##STR00272## ##STR00273## ##STR00274## ##STR00275## ##STR00276## ##STR00277## ##STR00278## ##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288##

##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315## ##STR00316## ##STR00317## ##STR00318## ##STR00319##

##STR00320## ##STR00321## ##STR00322## ##STR00323## ##STR00324## ##STR00325## ##STR00326## ##STR00327## ##STR00328## ##STR00329## ##STR00330## ##STR00331## ##STR00332## ##STR00333## ##STR00334## ##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339## ##STR00340## ##STR00341## ##STR00342## ##STR00343## ##STR00344## ##STR00345## ##STR00346## ##STR00347## ##STR00348## ##STR00349## ##STR00350## ##STR00351## ##STR00352## ##STR00353## ##STR00354## ##STR00355## ##STR00356## ##STR00357## ##STR00358## ##STR00359## ##STR00360## ##STR00361## ##STR00362## ##STR00363## ##STR00364## ##STR00365## ##STR00366## ##STR00367## ##STR00368## ##STR00369## ##STR00370##

2. Examples of Composition

[0570] The compounds in Examples were represented using symbols according to definitions in Table 4 described below. In Table 4, the configuration of 1,4-cyclohexylene is trans. A parenthesized number next to a symbolized compound corresponds to the number of the compound. A symbol (-) means any other liquid crystal compound. A proportion (percentage) of the liquid crystal compound is expressed in terms of weight percent (% by weight) based on the weight of the liquid crystal composition. Values of the characteristics of the composition were summarized in a last part. The characteristics were measured according to the methods described above, and measured values were directly described (without extrapolation).

TABLE-US-00004 TABLE 4 Method of description of compounds using symbols R(A.sub.1)Z.sub.1 . . . Z.sub.n(A.sub.n)R 1) Left-terminal group R Symbol C.sub.nH.sub.2n+1 n- C.sub.nH.sub.2n+1O nO C.sub.mH.sub.2m+1OC.sub.nH.sub.2n mOn CH.sub.2CH V C.sub.nH.sub.2n+1CHCH nV CH.sub.2CHC.sub.nH.sub.2n Vn C.sub.mH.sub.2m+1CHCHC.sub.nH.sub.2n mVn CF.sub.2CH VFF CF.sub.2CHC.sub.nH.sub.2n VFFn 2) Right-terminal group R Symbol C.sub.nH.sub.2n+1 -n OC.sub.nH.sub.2n+1 On COOCH.sub.3 EMe CHCH.sub.2 V CHCHC.sub.nH.sub.2n+1 Vn C.sub.nH.sub.2nCHCH.sub.2 nV C.sub.mH.sub.2mCHCHC.sub.nH.sub.2n+1 mVn CHCF.sub.2 VFF F F Cl CL OCF.sub.3 OCF3 OCF.sub.2H OCF2H CF.sub.3 CF3 OCHCHCF.sub.3 OVCF3 CN C 3) Bonding group Z.sub.n Symbol C.sub.nH.sub.2n n COO E CHCH V CH.sub.2O 1O OCH.sub.2 O1 CF.sub.2O X CC T 4) Ring structure A.sub.n Symbol [00371] H [00372] B [00373] B(F) [00374] B(2F) [00375] B(F,F) [00376] B(2F,5F) [00377] B(2F,3F) [00378] Py [00379] G [00380] ch 5) Examples of description Example 1. 3-HBCL [00381] Example 2. 5-HHBB(F,F)F [00382] Example 3. 3-HBO2 [00383] Example 4. 3-HBB(F,F)F [00384]

Use Example 1

[0571] 3-HHB(F,F)-F (6-3) 10% [0572] 3-H2HB(F,F)-F (6-15) 7% [0573] 4-H2HB(F,F)-F (6-15) 7% [0574] 5-H2HB(F,F)-F (6-15) 9% [0575] 3-HBB(F,F)-F (6-24) 19% [0576] 5-HBB(F,F)-F (6-24) 20% [0577] 3-H2BB(F,F)-F (6-27) 11% [0578] 5-HHBB(F,F)-F (7-6) 3% [0579] 5-HHEBB-F (7-17) 2% [0580] 3-HH2BB(F,F)-F (7-15) 3% [0581] 101-HBBH-4 (4-1) 5% [0582] 101-HBBH-5 (4-1) 4%

[0583] Compound (1-2-1) described below was added to the above composition in a proportion of 3% by weight.

##STR00385##

[0584] NI=100.2 C.; =35.1 mPa.Math.s; n=0.117; =8.9.

[0585] Use Example 2 [0586] 2-HB-C (8-1) 6% [0587] 3-HB-C (8-1) 13% [0588] 3-HB-O2 (2-5) 16% [0589] 2-BTB-1 (2-10) 4% [0590] 3-HHB-F (6-1) 5% [0591] 3-HHB-1 (3-1) 7% [0592] 3-HHB-O1 (3-1) 4% [0593] 3-HHB-3 (3-1) 13% [0594] 3-HHEB-F (6-10) 3% [0595] 5-HHEB-F (6-10) 3% [0596] 2-HHB(F)-F (6-2) 6% [0597] 3-HHB(F)-F (6-2) 6% [0598] 5-HHB(F)-F (6-2) 8% [0599] 3-HHB(F,F)-F (6-3) 6%

[0600] Compound (1-2-2) described below was added to the above composition in a proportion of 2% by weight.

##STR00386##

[0601] NI=93.1 C.; =15.9 mPa.Math.s; n=0.100; =4.8.

Use Example 3

[0602] 7-HB(F,F)-F (5-4) 5% [0603] 3-HB-O2 (2-5) 9% [0604] 2-HHB(F)-F (6-2) 12% [0605] 3-HHB(F)-F (6-2) 8% [0606] 5-HHB(F)-F (6-2) 8% [0607] 2-HBB(F)-F (6-23) 7% [0608] 3-HBB(F)-F (6-23) 10% [0609] 5-HBB(F)-F (6-23) 15% [0610] 2-HBB-F (6-22) 5% [0611] 3-HBB-F (6-22) 5% [0612] 5-HBB-F (6-22) 4% [0613] 3-HBB(F,F)-F (6-24) 4% [0614] 5-HBB(F,F)-F (6-24) 8%

[0615] Compound (1-2-18) described below was added to the above composition in a proportion of 4% by weight.

##STR00387##

[0616] NI=82.0 C.; =23.3 mPa.Math.s; n=0.113; =5.3.

Use Example 4

[0617] 5-HB-CL (5-2) 5% [0618] 7-HB(F)-F (5-3) 5% [0619] 3-HH-4 (2-1) 8% [0620] 3-HH-5 (2-1) 10% [0621] 3-HB-O2 (2-5) 10% [0622] 3-HHEB-F (6-10) 10% [0623] 5-HHEB-F (6-10) 9% [0624] 3-HHEB(F,F)-F (6-12) 9% [0625] 4-HHEB(F,F)-F (6-12) 5% [0626] 3-GHB(F,F)-F (6-109) 5% [0627] 4-GHB(F,F)-F (6-109) 6% [0628] 5-GHB(F,F)-F (6-109) 7% [0629] 2-HHB(F,F)-F (6-3) 5% [0630] 3-HHB(F,F)-F (6-3) 6%

[0631] Compound (1-2-28) described below was added to the above composition in a proportion of 7% by weight.

##STR00388##

[0632] NI=75.5 C.; =20.4 mPa.Math.s; n=0.069; =6.1.

Use Example 5

[0633] 5-HB-CL (5-2) 15% [0634] 3-HH-4 (2-1) 12% [0635] 3-HH-5 (2-1) 4% [0636] 3-HHB-F (6-1) 4% [0637] 3-HHB-CL (6-1) 3% [0638] 4-HHB-CL (6-1) 4% [0639] 3-HHB(F)-F (6-2) 11% [0640] 4-HHB(F)-F (6-2) 10% [0641] 5-HHB(F)-F (6-2) 8% [0642] 7-HHB(F)-F (6-2) 8% [0643] 5-HBB(F)-F (6-23) 3% [0644] 101-HBBH-5 (4-1) 3% [0645] 3-HHBB(F,F)-F (7-6) 3% [0646] 4-HHBB(F,F)-F (7-6) 3% [0647] 5-HHBB(F,F)-F (7-6) 3% [0648] 3-HH2BB(F,F)-F (7-15) 3% [0649] 4-HH2BB(F,F)-F (7-15) 3%

[0650] Compound (1-3-23) described below was added to the above composition in a proportion of 6% by weight.

##STR00389##

[0651] NI=115.9 C.; =19.6 mPa.Math.s; n=0.091; =3.8.

Use Example 6

[0652] 3-HB-CL (5-2) 11% [0653] 3-HH-4 (2-1) 14% [0654] 3-HB-O2 (2-5) 6% [0655] 3-HHB(F,F)-F (6-3) 5% [0656] 3-HBB(F,F)-F (6-24) 32% [0657] 5-HBB(F,F)-F (6-24) 22% [0658] 5-HBB(F)B-2 (4-5) 5% [0659] 5-HBB(F)B-3 (4-5) 5%

[0660] Compound (1-2-77) described below was added to the above composition in a proportion of 3% by weight.

##STR00390##

[0661] NI=72.9 C.; =19.7 mPa.Math.s; n=0.115; =5.5.

Use Example 7

[0662] 5-HB-F (5-2) 12% [0663] 6-HB-F (5-2) 9% [0664] 7-HB-F (5-2) 7% [0665] 2-HHB-OCF3 (6-1) 5% [0666] 3-HHB-OCF3 (6-1) 8% [0667] 4-HHB-OCF3 (6-1) 7% [0668] 5-HHB-OCF3 (6-1) 5% [0669] 3-HH2B-OCF3 (6-4) 5% [0670] 5-HH2B-OCF3 (6-4) 4% [0671] 3-HHB(F,F)-OCF2H (6-3) 3% [0672] 3-HHB(F,F)-OCF3 (6-3) 4% [0673] 3-HH2B(F)-F (6-5) 3% [0674] 3-HBB(F)-F (6-23) 10% [0675] 5-HBB(F)-F (6-23) 10% [0676] 5-HBBH-3 (4-1) 5% [0677] 3-HB(F)BH-3 (4-2) 3%

[0678] Compound (1-2-24) described below was added to the above composition in a proportion of 5% by weight.

##STR00391##

[0679] NI=89.1 C.; =15.1 mPa.Math.s; n=0.094; =4.3.

Use Example 8

[0680] 5-HB-CL (5-1) 14% [0681] 7-HB(F,F)-F (5-4) 5% [0682] 3-HH-4 (2-1) 11% [0683] 3-HH-5 (2-1) 6% [0684] 3-HB-O2 (2-5) 12% [0685] 3-HHB-1 (3-1) 10% [0686] 3-HHB-01 (3-1) 3% [0687] 2-HHB(F)-F (6-2) 5% [0688] 3-HHB(F)-F (6-2) 8% [0689] 5-HHB(F)-F (6-2) 7% [0690] 3-HHB(F,F)-F (6-3) 7% [0691] 3-H2HB(F,F)-F (6-15) 7% [0692] 4-H2HB(F,F)-F (6-15) 5%

[0693] Compound (1-3-68) described below was added to the above composition in a proportion of 2% by weight.

##STR00392##

[0694] NI=71.4 C.; =14.4 mPa.Math.s; n=0.071; =2.9.

Use Example 9

[0695] 5-HB-CL (5-1) 13% [0696] 3-HH-4 (2-5) 5% [0697] 3-HHB-1 (3-1) 5% [0698] 3-HHB(F,F)-F (6-3) 7% [0699] 3-HBB(F,F)-F (6-24) 21% [0700] 5-HBB(F,F)-F (6-24) 13% [0701] 3-HHEB(F,F)-F (6-12) 11% [0702] 4-HHEB(F,F)-F (6-12) 3% [0703] 5-HHEB(F,F)-F (6-12) 3% [0704] 2-HBEB(F,F)-F (6-39) 4% [0705] 3-HBEB(F,F)-F (6-39) 3% [0706] 5-HBEB(F,F)-F (6-39) 3% [0707] 3-HHBB(F,F)-F (7-6) 6% [0708] 5-HB-O2 (2-5) 3%

[0709] Compound (1-2-25) described below was added to the above composition in a proportion of 4% by weight.

##STR00393##

[0710] NI=116.7 C.; =20.6 mPa.Math.s; n=0.093; =4.0.

Use Example 10

[0711] 1V2-BEB(F,F)-C (8-15) 5% [0712] 3-HB-C (8-1) 20% [0713] 2-BTB-1 (2-10) 10% [0714] 5-HH-VFF (2-1) 27% [0715] 3-HHB-1 (3-1) 5% [0716] VFF-HHB-1 (3-1) 9% [0717] VFF2-HHB-1 (3-1) 12% [0718] 3-H2BTB-2 (3-17) 4% [0719] 3-H2BTB-3 (3-17) 4% [0720] 3-H2BTB-4 (3-17) 4%

[0721] Compound (1-4-127) described below was added to the above composition in a proportion of 3% by weight.

##STR00394##

[0722] NI=83.4 C.; =12.2 mPa.Math.s; n=0.131; =6.1.

Use Example 11

[0723] 3-HB-CL (5-2) 5% [0724] 5-HB-CL (5-2) 3% [0725] 3-HHB-OCF3 (6-1) 4% [0726] 3-H2HB-OCF3 (6-13) 5% [0727] 5-H4HB-OCF3 (6-19) 15% [0728] V-HHB(F)-F (6-2) 4% [0729] 3-HHB(F)-F (6-2) 6% [0730] 5-HHB(F)-F (6-2) 6% [0731] 3-H4HB(F,F)-CF3 (6-21) 8% [0732] 5-H4HB(F,F)-CF3 (6-21) 10% [0733] 5-H2HB(F,F)-F (6-15) 7% [0734] 5-H4HB(F,F)-F (6-21) 7% [0735] 2-H2BB(F)-F (6-26) 5% [0736] 3-H2BB(F)-F (6-26) 10% [0737] 3-HBEB(F,F)-F (6-39) 5%

[0738] Compound (1-2-17) described below was added to the above composition in a proportion of 5% by weight.

##STR00395##

[0739] NI=71.5 C.; =26.3 mPa.Math.s; n=0.097; =8.3.

Use Example 12

[0740] 3-HB-O2 (2-5) 13% [0741] 2-BTB-1 (2-10) 4% [0742] 3-HHB-1 (3-1) 9% [0743] 3-HHB-O1 (3-1) 4% [0744] 3-HHB-3 (3-1) 13% [0745] 3-HHB-F (6-1) 4% [0746] 2-HHB(F)-F (6-2) 7% [0747] 3-HHB(F)-F (6-2) 7% [0748] 5-HHB(F)-F (6-2) 7% [0749] 3-HHB(F,F)-F (6-3) 6% [0750] 3-HHEB-F (6-10) 4% [0751] 5-HHEB-F (6-10) 5% [0752] 2-HB-C (8-1) 5% [0753] 3-HB-C (8-1) 12%

[0754] Compound (1-9-1) described below was added to the above composition in a proportion of 2% by weight.

##STR00396##

[0755] NI=101.6 C.; =18.9 mPa.Math.s; n=0.102; =4.7.

Use Example 13

[0756] 3-HH-4 (2-1) 15% [0757] 3-HB-O2 (2-5) 9% [0758] 5-HBB(F)B-2 (4-5) 6% [0759] 5-HBB(F)B-3 (4-5) 4% [0760] 3-HB-CL (5-2) 14% [0761] 3-HHB(F,F)-F (6-3) 5% [0762] 3-HBB(F,F)-F (6-24) 26% [0763] 5-HBB(F,F)-F (6-24) 21%

[0764] Compound (1-9-2) described below was added to the above composition in a proportion of 3% by weight.

##STR00397##

[0765] NI=70.2 C.; =16.3 mPa.Math.s; n=0.112; =4.9.

Use Example 14

[0766] 3-HB-O2 (2-5) 8% [0767] 7-HB(F,F)-F (5-4) 5% [0768] 2-HHB(F)-F (6-2) 7% [0769] 3-HHB(F)-F (6-2) 8% [0770] 5-HHB(F)-F (6-2) 9% [0771] 2-HBB-F (6-22) 5% [0772] 3-HBB-F (6-22) 5% [0773] 5-HBB-F (6-22) 5% [0774] 2-HBB(F)-F (6-23) 10% [0775] 3-HBB(F)-F (6-23) 6% [0776] 5-HBB(F)-F (6-23) 14% [0777] 3-HBB(F,F)-F (6-24) 6% [0778] 5-HBB(F,F)-F (6-24) 12%

[0779] Compound (1-9-3) described below was added to the above composition in a proportion of 1% by weight.

##STR00398##

[0780] NI=80.9 C.; =24.3 mPa.Math.s; n=0.115; =5.4.

Use Example 15

[0781] 3-HH-4 (2-1) 10% [0782] 3-HH-5 (2-1) 4% [0783] 101-HBBH-5 (4-1) 4% [0784] 5-HB-CL (5-2) 16% [0785] 3-HHB-F (6-1) 5% [0786] 3-HHB-CL (6-1) 5% [0787] 4-HHB-CL (6-1) 4% [0788] 3-HHB(F)-F (6-2) 12% [0789] 4-HHB(F)-F (6-2) 7% [0790] 5-HHB(F)-F (6-2) 7% [0791] 7-HHB(F)-F (6-2) 6% [0792] 5-HBB(F)-F (6-23) 3% [0793] 3-HHBB(F,F)-F (7-6) 3% [0794] 4-HHBB(F,F)-F (7-6) 4% [0795] 5-HHBB(F,F)-F (7-6) 3% [0796] 3-HH2BB(F,F)-F (7-15) 3% [0797] 4-HH2BB(F,F)-F (7-15) 4%

[0798] Compound (1-9-4) described below was added to the above composition in a proportion of 4% by weight.

##STR00399##

[0799] NI=120.3 C.; =21.4 mPa.Math.s; n=0.096; =4.0.

Use Example 16

[0800] 101-HBBH-4 (4-1) 3% [0801] 101-HBBH-5 (4-1) 3% [0802] 3-HHB(F,F)-F (6-3) 8% [0803] 3-H2HB(F,F)-F (6-15) 7% [0804] 4-H2HB(F,F)-F (6-15) 6% [0805] 5-H2HB(F,F)-F (6-15) 10% [0806] 3-HBB(F,F)-F (6-24) 20% [0807] 5-HBB(F,F)-F (6-24) 22% [0808] 3-H2BB(F,F)-F (6-27) 12% [0809] 5-HHBB(F,F)-F (7-6) 3% [0810] 3-HH2BB(F. F)-F (7-15) 4% [0811] 5-HHEBB-F (7-17) 2%

[0812] Compound (1-9-5) described below was added to the above composition in a proportion of 7% by weight.

##STR00400##

[0813] NI=95.7 C.; =34.8 mPa.Math.s; n=0.116; =9.1.

Use Example 17

[0814] 5-HBBH-3 (4-1) 5% [0815] 3-HB(F)BH-3 (4-2) 3% [0816] 5-HB-F (5-2) 12% [0817] 6-HB-F (5-2) 9% [0818] 7-HB-F (5-2) 7% [0819] 2-HHB-OCF3 (6-1) 5% [0820] 3-HHB-OCF3 (6-1) 5% [0821] 4-HHB-OCF3 (6-1) 7% [0822] 5-HHB-OCF3 (6-1) 6% [0823] 3-HHB(F,F)-OCF2H (6-3) 5% [0824] 3-HHB(F,F)-OCF3 (6-3) 5% [0825] 3-HH2B-OCF3 (6-4) 5% [0826] 5-HH2B-OCF3 (6-4) 4% [0827] 3-HH2B(F)-F (6-5) 3% [0828] 3-HBB(F)-F (6-23) 8% [0829] 5-HBB(F)-F (6-23) 11%

[0830] Compound (1-9-6) described below was added to the above composition in a proportion of 5% by weight.

##STR00401##

[0831] NI=88.5 C.; =15.7 mPa.Math.s; n=0.093; =4.4.

Use Example 18

[0832] 3-HH-4 (2-1) 10% [0833] 5-HB-O2 (2-5) 5% [0834] 3-HHB-1 (3-1) 4% [0835] 5-HB-CL (5-2) 10% [0836] 3-HHB(F,F)-F (6-3) 8% [0837] 3-HHEB(F,F)-F (6-12) 9% [0838] 4-HHEB(F,F)-F (6-12) 3% [0839] 5-HHEB(F,F)-F (6-12) 3% [0840] 3-HBB(F,F)-F (6-24) 19% [0841] 5-HBB(F,F)-F (6-24) 14% [0842] 2-HBEB(F,F)-F (6-39) 3% [0843] 3-HBEB(F,F)-F (6-39) 4% [0844] 5-HBEB(F,F)-F (6-39) 3% [0845] 3-HHBB(F,F)-F (7-6) 5%

[0846] Compound (1-9-7) described below was added to the above composition in a proportion of 2% by weight.

##STR00402##

[0847] NI=76.9 C.; =19.3 mPa.Math.s; n=0.099; =8.2.

Use Example 19

[0848] 3-HB-CL (5-2) 4% [0849] 5-HB-CL (5-2) 6% [0850] 3-HHB-OCF3 (6-1) 6% [0851] V-HHB(F)-F (6-2) 4% [0852] 3-HHB(F)-F (6-2) 4% [0853] 5-HHB(F)-F (6-2) 6% [0854] 3-H2HB-OCF3 (6-13) 5% [0855] 5-H2HB(F,F)-F (6-15) 6% [0856] 5-H4HB-OCF3 (6-19) 15% [0857] 3-H4HB(F,F)-CF3 (6-21) 8% [0858] 5-H4HB(F,F)-CF3 (6-21) 10% [0859] 5-H4HB(F,F)-F (6-21) 7% [0860] 2-H2BB(F)-F (6-26) 5% [0861] 3-H2BB(F)-F (6-26) 8% [0862] 3-HBEB(F,F)-F (6-39) 6%

[0863] Compound (1-9-8) described below was added to the above composition in a proportion of 3% by weight.

##STR00403##

[0864] NI=70.4 C.; =25.7 mPa.Math.s; n=0.096; =8.5.

Use Example 20

[0865] 3-HH-4 (2-1) 8% [0866] 3-HH-5 (2-1) 6% [0867] 3-HB-O2 (2-5) 14% [0868] 3-HHB-1 (3-1) 8% [0869] 3-HHB-O1 (3-1) 6% [0870] 5-HB-CL (5-2) 15% [0871] 7-HB(F,F)-F (5-4) 5% [0872] 2-HHB(F)-F (6-2) 7% [0873] 3-HHB(F)-F (6-2) 7% [0874] 5-HHB(F)-F (6-2) 7% [0875] 3-HHB(F,F)-F (6-3) 7% [0876] 3-H2HB(F,F)-F (6-15) 5% [0877] 4-H2HB(F,F)-F (6-15) 5%

[0878] Compound (1-10-1) described below was added to the above composition in a proportion of 1% by weight.

##STR00404##

NI=71.4 C.; =14.7 mPa.Math.s; n=0.073; =3.0.

Use Example 21

[0879] 3-HH-4 (2-1) 10% [0880] 3-HH-5 (2-1) 11% [0881] 3-HB-O2 (2-5) 10% [0882] 5-HB-CL (5-2) 3% [0883] 7-HB(F)-F (5-3) 8% [0884] 2-HHB(F,F)-F (6-3) 5% [0885] 3-HHB(F,F)-F (6-3) 4% [0886] 3-HHEB-F (6-10) 9% [0887] 5-HHEB-F (6-10) 8% [0888] 3-HHEB(F,F)-F (6-12) 8% [0889] 4-HHEB(F,F)-F (6-12) 5% [0890] 3-GHB(F,F)-F (6-109) 4% [0891] 4-GHB(F,F)-F (6-109) 7% [0892] 5-GHB(F,F)-F (6-109) 8%

[0893] Compound (1-10-2) described below was added to the above composition in a proportion of 2% by weight.

##STR00405##

[0894] NI=70.9 C.; =19.0 mPa.Math.s; n=0.065; =5.9.

Use Example 22

[0895] 3-HH-4 (2-1) 10% [0896] 3-HH-5 (2-1) 8% [0897] 101-HBBH-5 (4-1) 3% [0898] 5-HB-CL (5-2) 10% [0899] 3-HHB-F (6-1) 5% [0900] 3-HHB-CL (6-1) 3% [0901] 4-HHB-CL (6-1) 4% [0902] 3-HHB(F)-F (6-2) 8% [0903] 4-HHB(F)-F (6-2) 9% [0904] 5-HBB(F)-F (6-2) 10% [0905] 7-HHB(F)-F (6-2) 8% [0906] 5-HBB(F)-F (6-23) 5% [0907] 3-HHBB(F,F)-F (7-6) 4% [0908] 4-HHBB(F,F)-F (7-6) 3% [0909] 5-HHBB(F,F)-F (7-6) 4% [0910] 3-HH2BB(F,F)-F (7-15) 3% [0911] 4-HH2BB(F,F)-F (7-15) 3%

[0912] Compound (1-10-3) described below was added to the above composition in a proportion of 4% by weight.

##STR00406##

[0913] NI=124.8 C.; =22.6 mPa.Math.s; n=0.094; =3.9.

Use Example 23

[0914] 3-HH-4 (2-1) 10% [0915] 3-HB-O2 (2-5) 4% [0916] 5-HB-O2 (2-5) 5% [0917] 3-HHB-1 (3-1) 5% [0918] 5-HB-CL (5-2) 6% [0919] 3-HHB(F,F)-F (6-3) 6% [0920] 3-HHEB(F,F)-F (6-12) 8% [0921] 4-HHEB(F,F)-F (6-12) 3% [0922] 5-HHEB(F,F)-F (6-12) 3% [0923] 3-HBB(F,F)-F (6-24) 18% [0924] 5-HBB(F,F)-F (6-24) 13% [0925] 2-HBEB(F,F)-F (6-39) 4% [0926] 3-HBEB(F,F)-F (6-39) 5% [0927] 5-HBEB(F,F)-F (6-39) 4% [0928] 3-HHBB(F,F)-F (7-6) 6%

[0929] Compound (1-10-4) described below was added to the above composition in a proportion of 3% by weight.

##STR00407##

[0930] NI=79.9 C.; =20.0 mPa.Math.s; n=0.101; =8.3.

Use Example 24

[0931] 3-HB-O2 (2-5) 9% [0932] 7-HB(F,F)-F (5-4) 5% [0933] 2-HHB(F)-F (6-2) 9% [0934] 3-HHB(F)-F (6-2) 9% [0935] 5-HHB(F)-F (6-2) 9% [0936] 2-HBB-F (6-22) 5% [0937] 3-HBB-F (6-22) 5% [0938] 5-HBB-F (6-22) 5% [0939] 2-HBB(F)-F (6-23) 7% [0940] 3-HBB(F)-F (6-23) 5% [0941] 5-HBB(F)-F (6-23) 13% [0942] 3-HBB(F,F)-F (6-24) 8% [0943] 5-HBB(F,F)-F (6-24) 11%

[0944] Compound (1-9-11) described below was added to the above composition in a proportion of 1% by weight.

##STR00408##

[0945] NI=80.8 C.; =203.7 mPa.Math.s; n=0.112; =5.4.

Use Example 25

[0946] 5-HBBH-3 (4-1) 6% [0947] 3-HB(F)BH-3 (4-2) 3% [0948] 5-HB-F (5-2) 12% [0949] 6-HB-F (5-2) 9% [0950] 7-HB-F (5-2) 7% [0951] 2-HHB-OCF3 (6-1) 7% [0952] 3-HHB-OCF3 (6-1) 6% [0953] 4-HHB-OCF3 (6-1) 7% [0954] 5-HHB-OCF3 (6-1) 4% [0955] 3-HHB(F,F)-OCF2H (6-3) 4% [0956] 3-HBB(F,F)-OCF3 (6-3) 4% [0957] 3-HH2B-OCF3 (6-4) 5% [0958] 5-HH2B-OCF3 (6-4) 4% [0959] 3-HH2B(F)-F (6-5) 3% [0960] 3-HBB(F)-F (6-23) 6% [0961] 5-HBB(F)-F (6-23) 13%

[0962] Compound (1-9-12) described below was added to the above composition in a proportion of 3% by weight.

##STR00409##

[0963] NI=90.1 C.; =15.4 mPa.Math.s; n=0.093; =4.3.

Use Example 26

[0964] 3-HH-4 (2-1) 12% [0965] 3-HH-5 (2-1) 12% [0966] 3-HB-O2 (2-5) 10% [0967] 5-HB-CL (5-2) 4% [0968] 7-HB(F)-F (5-3) 5% [0969] 2-HHB(F,F)-F (6-3) 5% [0970] 3-HHB(F,F)-F (6-3) 5% [0971] 3-HHEB-F (6-10) 7% [0972] 5-HHEB-F (6-10) 7% [0973] 3-HHEB(F,F)-F (6-12) 10% [0974] 4-HHEB(F,F)-F (6-12) 3% [0975] 3-GHB(F,F)-F (6-109) 6% [0976] 4-GHB(F,F)-F (6-109) 8% [0977] 5-GHB(F,F)-F (6-109) 6%

[0978] Compound (1-9-9) described below was added to the above composition in a proportion of 3% by weight.

##STR00410##

[0979] NI=70.8 C.; =18.8 mPa.Math.s; n=0.065; =6.1.

Use Example 27

[0980] 3-HH-4 (2-1) 7% [0981] 3-HB-O2 (2-5) 3% [0982] 5-HB-O2 (2-5) 4% [0983] 3-HHB-1 (3-1) 5% [0984] 5-HB-CL (5-2) 8% [0985] 3-HHB(F,F)-F (6-3) 9% [0986] 3-HHEB(F,F)-F (6-12) 9% [0987] 4-HHEB(F,F)-F (6-12) 4% [0988] 5-HHEB(F,F)-F (6-12) 4% [0989] 3-HBB(F,F)-F (6-24) 18% [0990] 5-HBB(F,F)-F (6-24) 13% [0991] 2-HBEB(F,F)-F (6-39) 4% [0992] 3-HBEB(F,F)-F (6-39) 4% [0993] 5-HBEB(F,F)-F (6-39) 4% [0994] 3-HHBB(F,F)-F (7-6) 4%

[0995] Compound (1-9-10) described below was added to the above composition in a proportion of 3% by weight.

##STR00411##

[0996] NI=77.9 C.; =20.6 mPa.Math.s; n=0.100; =8.5.

Use Example 28

[0997] 3-HH-4 (2-1) 9% [0998] 3-HB-O2 (2-5) 5% [0999] 5-HB-O2 (2-5) 5% [1000] 3-HHB-1 (3-1) 6% [1001] 5-HB-CL (5-2) 5% [1002] 3-HHB(F,F)-F (6-3) 5% [1003] 3-HHEB(F,F)-F (6-12) 6% [1004] 4-HHEB(F,F)-F (6-12) 5% [1005] 5-HHEB(F,F)-F (6-12) 4% [1006] 3-HBB(F,F)-F (6-24) 17% [1007] 5-HBB(F,F)-F (6-24) 13% [1008] 2-HBEB(F,F)-F (6-39) 5% [1009] 3-HBEB(F,F)-F (6-39) 5% [1010] 5-HBEB(F,F)-F (6-39) 5% [1011] 3-HHBB(F,F)-F (7-6) 5%

[1012] Compound (1-9-41) described below was added to the above composition in a proportion of 2% by weight.

##STR00412##

[1013] NI=80.2 C.; =20.5 mPa.Math.s; n=0.101; =8.5.

Use Example 29

[1014] 3-HB-O2 (2-5) 16% [1015] 2-BTB-1 (2-10) 4% [1016] 3-HHB-1 (3-1) 6% [1017] 3-HHB-01 (3-1) 5% [1018] 3-HHB-3 (3-1) 10% [1019] 3-HHB-F (6-1) 5% [1020] 2-HHB(F)-F (6-2) 5% [1021] 3-HHB(F)-F (6-2) 5% [1022] 5-HHB(F)-F (6-2) 5% [1023] 3-HHB(F,F)-F (6-3) 6% [1024] 3-HHEB-F (6-10) 6% [1025] 5-HHEB-F (6-10) 6% [1026] 2-HB-C (8-1) 6% [1027] 3-HB-C (8-1) 15%

[1028] Compound (1-9-42) described below was added to the above composition in a proportion of 2% by weight.

##STR00413##

[1029] NI=98.9 C.; =19.5 mPa.Math.s; n=0.105; =4.9.

Use Example 30

[1030] 3-HH-4 (2-1) 10% [1031] 3-HH-5 (2-1) 5% [1032] 101-HBBH-5 (4-1) 5% [1033] 5-HB-CL (5-2) 15% [1034] 3-HHB-F (6-1) 4% [1035] 3-HHB-CL (6-1) 4% [1036] 4-HHB-CL (6-1) 4% [1037] 3-HHB(F)-F (6-2) 10% [1038] 4-HHB(F)-F (6-2) 5% [1039] 5-HHB(F)-F (6-2) 5% [1040] 7-HHB(F)-F (6-2) 7% [1041] 5-HBB(F)-F (6-23) 5% [1042] 3-HHBB(F,F)-F (7-6) 5% [1043] 4-HHBB(F,F)-F (7-6) 5% [1044] 5-HHBB(F,F)-F (7-6) 5% [1045] 3-HH2BB(F,F)-F (7-15) 3% [1046] 4-HH2BB(F,F)-F (7-15) 3%

[1047] Compound (1-9-52) described below was added to the above composition in a proportion of 3% by weight.

##STR00414##

[1048] NI=126.8 C.; =25.3 mPa.Math.s; n=0.100; =4.2.

Use Example 31

[1049] 3-HB-CL (5-2) 4% [1050] 5-HB-CL (5-2) 5% [1051] 3-HHB-OCF3 (6-1) 6% [1052] V-HHB(F)-F (6-2) 6% [1053] 3-HHB(F)-F (6-2) 6% [1054] 5-HHB(F)-F (6-2) 6% [1055] 3-H2HB-OCF3 (6-13) 5% [1056] 5-H2HB(F,F)-F (6-15) 5% [1057] 5-H4HB-OCF3 (6-19) 15% [1058] 3-H4HB(F,F)-CF3 (6-21) 8% [1059] 5-H4HB(F,F)-CF3 (6-21) 10% [1060] 5-H4HB(F,F)-F (6-21) 7% [1061] 2-H2BB(F)-F (6-26) 5% [1062] 3-H2BB(F)-F (6-26) 6% [1063] 3-HBEB(F,F)-F (6-39) 6%

[1064] Compound (1-9-51) described below was added to the above composition in a proportion of 1.5% by weight.

##STR00415##

[1065] NI=72.0 C.; =25.9 mPa.Math.s; n=0.096; =8.5.

Use Example 32

[1066] 101-HBBH-4 (4-1) 5% [1067] 101-HBBH-5 (4-1) 5% [1068] 3-HHB(F,F)-F (6-3) 5% [1069] 3-H2HB(F,F)-F (6-15) 6% [1070] 4-H2HB(F,F)-F (6-15) 7% [1071] 5-H2HB(F,F)-F (6-15) 7% [1072] 3-HBB(F,F)-F (6-24) 20% [1073] 5-HBB(F,F)-F (6-24) 22% [1074] 3-H2BB(F,F)-F (6-27) 15% [1075] 5-HHBB(F,F)-F (7-6) 3% [1076] 3-HH2BB(F,F)-F (7-15) 3% [1077] 5-HHEBB-F (7-17) 2%

[1078] Compound (1-9-53) described below was added to the above composition in a proportion of 3% by weight.

##STR00416##

[1079] NI=100.2 C.; =35.9 mPa.Math.s; n=0.121; =9.0.

Use Example 33

[1080] 3-HH-4 (2-1) 16% [1081] 3-HB-O2 (2-5) 10% [1082] 5-HBB(F)B-2 (4-5) 5% [1083] 5-HBB(F)B-3 (4-5) 4% [1084] 3-HB-CL (5-2) 10% [1085] 3-HHB(F,F)-F (6-3) 6% [1086] 3-HBB(F,F)-F (6-24) 27% [1087] 5-HBB(F,F)-F (6-24) 22%

[1088] Compound (1-9-54) described below was added to the above composition in a proportion of 2% by weight.

##STR00417##

[1089] NI=71.2 C.; =17.1 mPa.Math.s; n=0.111; =5.0.

Use Example 34

[1090] 3-HH-4 (2-1) 6% [1091] 3-HH-5 (2-1) 6% [1092] 3-HB-O2 (2-5) 15% [1093] 3-HHB-1 (3-1) 6% [1094] 3-HHB-01 (3-1) 9% [1095] 5-HB-CL (5-2) 15% [1096] 7-HB(F,F)-F (5-4) 6% [1097] 2-HHB(F)-F (6-2) 6% [1098] 3-HHB(F)-F (6-2) 6% [1099] 5-HHB(F)-F (6-2) 7% [1100] 3-HHB(F,F)-F (6-3) 6% [1101] 3-H2HB(F,F)-F (6-15) 6% [1102] 4-H2HB(F,F)-F (6-15) 6%

[1103] Compound (1-9-55) described below was added to the above composition in a proportion of 1% by weight.

##STR00418##

[1104] NI=70.7 C.; =15.3 mPa.Math.s; n=0.074; =3.0.

Use Example 35

[1105] 3-HH-4 (2-1) 13% [1106] 3-HH-5 (2-1) 6% [1107] 101-HBBH-5 (4-1) 4% [1108] 5-HB-CL (5-2) 13% [1109] 3-HHB-F (6-1) 3% [1110] 3-HHB-CL (6-1) 4% [1111] 4-HHB-CL (6-1) 4% [1112] 3-HHB(F)-F (6-2) 7% [1113] 4-HHB(F)-F (6-2) 7% [1114] 5-HHB(F)-F (6-2) 7% [1115] 7-HHB(F)-F (6-2) 7% [1116] 5-HBB(F)-F (6-23) 7% [1117] 3-HHBB(F,F)-F (7-6) 4% [1118] 4-HHBB(F,F)-F (7-6) 4% [1119] 5-HHBB(F,F)-F (7-6) 4% [1120] 3-HH2BB(F,F)-F (7-15) 3% [1121] 4-HH2BB(F,F)-F (7-15) 3%

[1122] Compound (1-9-56) described below was added to the above composition in a proportion of 3% by weight.

##STR00419##

[1123] NI=124.8 C.; =23.5 mPa.Math.s; n=0.096; =3.9.

Use Example 36

[1124] 3-HH-4 (2-1) 11% [1125] 3-HH-5 (2-1) 5% [1126] 101-HBBH-5 (4-1) 5% [1127] 5-HB-CL (5-2) 15% [1128] 3-HHB-F (6-1) 5% [1129] 3-HHB-CL (6-1) 3% [1130] 4-HHB-CL (6-1) 4% [1131] 3-HHB(F)-F (6-2) 10% [1132] 4-HHB(F)-F (6-2) 8% [1133] 5-HHB(F)-F (6-2) 7% [1134] 7-HHB(F)-F (6-2) 6% [1135] 5-HBB(F)-F (6-23) 5% [1136] 3-HHBB(F,F)-F (7-6) 4% [1137] 4-HHBB(F,F)-F (7-6) 3% [1138] 5-HHBB(F,F)-F (7-6) 3% [1139] 3-HH2BB(F,F)-F (7-15) 3% [1140] 4-HH2BB(F,F)-F (7-15) 3%

[1141] Compound (1-9-57) described below was added to the above composition in a proportion of 2% by weight.

##STR00420##

[1142] NI=121.9 C.; =21.8 mPa.Math.s; n=0.096; =3.9.

INDUSTRIAL APPLICABILITY

[1143] A liquid crystal composition containing compound (1) can be used in a display device such as a liquid crystal projector and a liquid crystal television.