JPH0825956B2 - New liquid crystal compound - Google Patents

Description

The present invention relates to a new liquid crystal compound.

More specifically, the present invention relates to the general formula [I] [In the formula, R ¹ and R ² are each independently a C _{2 to} C ₁₆ linear alkyl group, * is an asymmetric center, and X is O—CH ₂ or CH ₂ —O. ] It is related with the optically active compound represented by these, or its racemate, and the liquid-crystal composition containing this compound.

Conventionally, liquid crystal compounds have been used as liquid crystal materials in various electro-optical display devices. The optimum liquid crystal substance properties vary depending on the display method, but the
It is required to be physically, chemically and electrically stable against light, electric field and the like.

In addition, the temperature range of the liquid crystal is wide, the driving voltage is low, the response speed is fast, and the time division characteristic is good.
A wide viewing angle is also required.

However, no single compound satisfying these conditions has been obtained so far, and in practice, several kinds of liquid crystal compounds or non-liquid crystal compounds each having excellent properties are mixed to prepare a liquid crystal composition. The current situation is to obtain a material that can withstand some use.

An object of the present invention is to provide a compound which is advantageous as a material for a liquid crystal composition having excellent practical performance. For this purpose, the present inventors have synthesized a large number of compounds having a 2-substituted propionic acid ester skeleton in the compound, and have found the compound of the present invention.

The compound of the present invention is colorless to pale yellow in a pure state, is chemically stable, and has a wide liquid crystal temperature range.

In addition, other liquid crystal materials, such as existing biphenyl-based materials,
It has excellent compatibility with phenylcyclohexane type, benzoic acid phenyl ester type, cyclohexanecarboxylic acid phenyl ester type, Schiff base type, azoxy type, phenylpyrimidine type, phenyl metadioxane type, etc. We have found that it is a useful component that constitutes a liquid crystal composition with a wide liquid crystal temperature range and excellent response characteristics.

The compound of the present invention can be produced by various methods, for example, the following method.

(1) etherification of 1-n-alkyloxy-4-halomethyl-benzene and n-alkyl 2- (4'-hydroxy-4-biphenyloxy) propionate in the presence of a base, (2) 4-n -Alkyloxy-phenol, 2-
Etherification of (4'-halomethyl-4-biphenyloxy) n-alkyl propionate in the presence of a base, (3) 4-{[4 '-(1- (n-alkyloxycarbonyl) ethyl) oxy-4 Alkylation of -biphenyl] methyloxy} -phenol by reaction with an n-alkyl halide in the presence of a base in an anhydrous solvent, (4) 4-{[4 '-(1- (n-alkyloxycarbonyl)) Alkylation of ethyl) oxy-4-biphenyl] oxymethyl} -phenol by reaction with an n-alkyl halide in the presence of a base in an anhydrous solvent, (5) 2- (4 ′-(4-alkoxybenzyloxy) )
Esterification by reaction of acid halide of -4-biphenyloxy) propionic acid with n-alkyl alcohol, (6) acid halide of 2- (4 '-(4-alkoxyphenoxy) methyl-4-biphenyloxy) propionic acid esterification by reaction of n-alkyl alcohol, (7) in the presence of a base of 4-hydroxy-4 ′-(4-n-alkyloxyphenyl) methyloxy) biphenyl and n-alkyl 2- (sulfonyloxy) propionate Condensation reaction with (8) 4-hydroxy-4 ′-(4-n-alkyloxyphenyl) oxymethyl) biphenyl and n-alkyl 2- (sulfonyloxy) propionate in the presence of a base, Etc.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.

[Example 1] Preparation of optically active 2- [4 '-(4-n-octyloxybenzyloxy) -4-biphenyloxy] propionic acid n-butyl ester.

Optically active 2- (4'-hydroxy-4-biphenyloxy) propionic acid n-butyl ester (314 mg) was dissolved in acetonitrile (10 ml), and 4-n-octyloxybenzyl chloride (358 mg) and potassium carbonate (304 mg) were added. Heated to reflux for hours. 30 ml of water and chloroform in the reaction solution
The crude product obtained by adding 30 ml of liquid and separating the solution, washing the chloroform layer with water and concentrating, was purified by silica gel column chromatography to give optically active 2- [4 '-(4-n-octyloxybenzyloxy). -4-Biphenyloxy]
250 mg (yield 47%) of propionic acid n-butyl ester was obtained.

▲ [α] ²⁵ _D ▼ + 18.3 ° (c = 1.04, chloroform) IR (KBr): 2900,1750,1605,1500,1240,810cm ^-1 NMR (CDCl ₃ ) δ7.6-6.8 (m, 12H ), 5.00 (s, 2H), 4.78 (q, J = 7Hz, 1H), 4.17 (t, J = 6Hz, 2H), 3.95 (t, J
= 6Hz, 2H), 1.62 (d, J = 7Hz, 3H), 2.0 to 0.8 (m, 22H) MS (m / e): 532 (M ⁺ , 27), 326 (12), 219 (100), 107 (71) [Example 2] Production of optically active 2- [4 '-(4-n-octyloxybenzyloxy) -4-biphenyloxy] propionic acid n-hexyl ester.

Optically active 2- (4'-hydroxy-4-biphenyloxy) propionic acid n-butyl ester (342 mg) was dissolved in acetonitrile (10 ml), and 4-n-octyloxybenzyl chloride (358 mg) and potassium carbonate (304 mg) were added. Heated to reflux for hours. 30 ml of water and chloroform in the reaction solution
The crude product obtained by adding 30 ml of liquid and separating the solution, washing the chloroform layer with water and concentrating, was purified by silica gel column chromatography to give optically active 2- [4 '-(4-n-octyloxybenzyloxy). -4-Biphenyloxy]
360 mg of propionic acid n-hexyl ester (64% yield)
I got

▲ [α] ²⁵ _D ▼ + 19.1 ° (c = 0.721 chloroform) IR (KBr): 2900,1740,1605,1500,1240,810cm ^-1 NMR (CDCl ₃ ) δ7.6-6.8 (m, 12H) , 5.00 (s, 2H), 4.75 (q, J = 7Hz, 1H), 4.18 (t, J = 6Hz, 2H), 3.98 (t, J = 6Hz, 2H), 1.65 (d, J = 7Hz, 3H) ), 2.0 to 0.9 (m, 26H) MS (m / e): 560 (M ⁺ , 22), 342 (11), 219 (100), 107 (57) [Example 3] Preparation of optically active 2- [4 '-(4-n-octyloxyphenoxymethyl) -4-biphenyloxy] propionic acid n-hexyl ester.

202 mg of optically active 2- (p-toluenesulfonyloxy) propionic acid n-hexyl ester (▲ [α] ²⁵ _D ▼
−26.7 ° (c = 1.4, chloroform)) and 4-hydroxy-4 ′-(4-n-octyloxyphenoxymethyl) biphenyl 164 mg were dissolved in acetonitrile 10 ml,
138 mg of potassium carbonate was added thereto, and the mixture was heated under reflux for 16 hours.

30 ml of water and 30 ml of chloroform were added to the reaction mixture for liquid separation,
The crude product obtained by washing the chloroform layer with water and then concentrating it was separated and purified by silica gel column chromatography to give optically active 2- [4 '-(4-n-octyloxyphenoxymethyl) -4-biphenyloxy] propionic acid. 182 mg (yield 60%) of n-hexyl ester was obtained.

▲ [α] ²⁵ _D ▼ + 22.2 ° (c = 0.563 chloroform) IR (KBr): 2900,1740,1605,1510,820cm ^-1 NMR (CDCl ₃ ) δ7.6〜6.8 (m, 12H), 4.96 (S, 2H), 4.72 (q, J = 7Hz, 1H), 4.10 (t, J = 6Hz, 2H), 3.84 (t, J = 6Hz, 2H), 1.60 (d, J = 7Hz, 3H), 1.9 to 0.7 (m, 26H) MS (m / e): 560 (M ⁺ , 3), 339 (100), 183 (4)

Claims (2)

[Claims] 1. A general formula [I]: [In the formula, R ¹ and R ² each independently represent a C _{2 to} C ₁₆ linear alkyl group, * represents an asymmetric center, and X represents O—CH ₂ or CH ₂ —O. ] The optically active compound represented by these, or its racemic body. 2. A compound of the general formula [I]: [In the formula, R ¹ and R ² are each independently a C _{2 to} C ₁₆ linear alkyl group, * is an asymmetric center, and X is O—CH ₂ or CH ₂ —O. ] The liquid crystal composition characterized by containing 1 type (s) or 2 or more types of the optically active compound represented by these.