Liquid crystal compound having difluoropropenyleneoxy bonding group
View Patent ↗The invention provides a liquid crystal compound having general physical properties necessary for the compound, namely stability to heat, light and so forth, a wide temperature range of a liquid crystal phase, a high clearing point, a good compatibility with other compounds, a large optical anisotropy and a large dielectric anisotropy; a compound represented by formula (1): wherein, for example, R 1 is alkyl having 1 to 20 carbons; ring A 1 and ring A 4 each are 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which arbitrary hydrogen is replaced by halogen; Z 1 and Z 4 each are a single bond; L 1 , L 2 , L 3 and L 4 each are hydrogen or fluorine; and X 1 is fluorine, chlorine, —CF 3 or —OCF 3 .
1. A compound represented by formula (1):
wherein, in formula (1), R 1 is alkyl having 1 to 20 carbons, and in the alkyl, arbitrary —CH 2 — may be replaced by —O—, —S— or —CH═CH—; ring A 1 and ring A 4 are independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, tetrahydropyran-2,5-diyl, 1,4-phenylene, or 1,4-phenylene in which arbitrary hydrogen is replaced by halogen; Z 1 and Z 4 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CF═CF—, —(CH 2 ) 4 —, —(CH 2 ) 2 CF 2 O—, —(CH 2 ) 2 OCF 2 —, —CF 2 —O—(CH 2 ) 2 —, —CF 2 (CH 2 ) 2 —, —CH═CH— (CH 2 ) 2 — or —(CH 2 ) 2 —CH═CH—; L 1 , L 2 , L 3 and L 4 are independently hydrogen, fluorine or chlorine; X 1 is hydrogen, halogen, —C≡N, —N═C═S, —SF 5 or alkyl having 1 to 10 carbons, and in the alkyl, arbitrary —CH 2 — may be replaced by —O—, —S— or —CH═CH—, and arbitrary hydrogen may be replaced by halogen; 1 and o are independently an integer from 0 to 3, and a sum of 1 and o is 3 or less; and when 1 is 1, o is 0, ring A 1 is 1,4-phenylene and X 1 is fluorine, at least one of L 1 , L 2 , L 3 and L 4 is hydrogen.
2. The compound according to claim 1 , wherein, in formula (1), R 1 is alkyl having 1 to 20 carbons, alkenyl having 2 to 21 carbons, alkoxy having 1 to 19 carbons, alkenyloxy having 2 to 20 carbons or alkylthio having 1 to 19 carbons; X 1 is hydrogen, halogen, —C≡N, —N═C═S, —SF S , alkyl having 1 to 10 carbons, alkenyl having 2 to 11 carbons, alkoxy having 1 to 9 carbons, alkenyloxy having 2 to 10 carbons, thioalkyl having 1 to 9 carbons, —CH 2 F, —CHF 2 , —CF 3 , —(CH 2 ) 2 —F, —CF 2 CH 2 F, —CF 2 CHF 2 , —CH 2 CF 3 , —CF 2 CF 3 , —(CH 2 ) 3 —F, —(CF 2 ) 3 —F, —CF 2 CHFCF 3 , —CHFCF 2 CF 3 , —(CH 2 ) 4 —F, —(CF 2 ) 4 —F, —(CH 2 ) 5 —F, —(CF 2 ) 5 —F, —OCH 2 F, —OCHF 2 , —OCF 3 , —O—(CH 2 ) 2 —F, —OCF 2 CH 2 F, —OCF 2 CHF 2 , —OCH 2 CF 3 , —O—(CH 2 ) 3 —F, —O— (CF 2 ) 3 —F, —OCF 2 CHFCF 3 , —OCHFCF 2 CF 3 , —O(CH 2 ) 4 —F, —O— (CF 2 ) 4 —F, —O—(CH 2 ) 5 —F, —O— (CF 2 ) 5 —F, —CH═CHF, —CH═CF 2 , —CF═CHF, —CH═CHCH 2 F, —CH═CHCF 3 , —(CH 2 ) 2 —CH═CF 2 , —CH 2 CH═CHCF 3 or —CH═CHCF 2 CF 3 .
3. The compound according to claim 1 , wherein, in formula (1), R 1 is alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyloxy having 2 to 12 carbons; Z 1 and Z 4 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —CF 2 O—, —CH 2 O— or —OCH 2 —; and X 1 is fluorine, chlorine, —C≡N, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 or —OCH 2 F.
4. The compound according to claim 1 , wherein, in formula (1), R 1 is alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons or alkoxy having 1 to 12 carbons; Z 1 and Z 4 are independently a single bond, —CH 2 CH 2 — or —CH═CH—; and X 1 is fluorine, chlorine, —CF 3 or —OCF 3 .
5. The compound according to claim 1 , wherein the compound is represented by any one of formula (1-1) to formula (1-5):
wherein, in the formulas, R 1 is alkyl having 1 to 12 carbons or alkenyl having 2 to 12 carbons; ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, tetrahydropyran-2,5-diyl, 1,4-phenylene, or 1,4-phenylene in which arbitrary hydrogen is replaced by halogen; L 1 , L 2 , L 3 and L 4 are independently hydrogen, chlorine or fluorine; X 1 is fluorine, chlorine, —CF 3 or —OCF 3 ; and then, when ring A 1 is 1,4-phenylene and X 1 is fluorine in formula (1-1), at least one of L 1 , L 2 , L 3 and L 4 is hydrogen.
6. The compound according to claim 1 , wherein the compound is represented by any one of formula (1-6) to formula (1-38):
wherein, in the formulas, R 1 is alkyl having 1 to 12 carbons; L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 and L 9 are independently hydrogen, chlorine or fluorine; X 1 is fluorine, chlorine, —CF 3 or —OCF 3 ; and then, when X 1 is fluorine in formula (1-6), at least one of L 1 , L 2 , L 3 and L 4 is hydrogen.
7. The compound according to claim 1 , wherein the compound is represented by any one of formula (1-39) to formula (1-49):
wherein, in the formulas, R 1 is alkyl having 1 to 12 carbons; L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 and L 9 are independently hydrogen or fluorine; X 1 is fluorine, chlorine, —CF 3 or —OCF 3 ; and then, when X 1 is fluorine in formula (1-39), at least one of L 1 , L 2 , L 3 and L 4 is hydrogen.