JPS6127972A - 5-alkyl-2-(4-(beta-alkoxyethoxy)-4'-biphenylyl)pyrimidine - Google Patents

Abstract

NEW MATERIAL:A 5-alkyl-2-[4-(beta-alkoxyethoxy)-4'-biphenylyl]pyrimidine expressed by formula I (R<1> and R<2> are 1-10C alkyl). EXAMPLE:5-Propyl-2-[4-(beta-ethoxyethoxy)-4'-biphenylyl]pyrimidine. USE:A component in liquid crystal materials, capable of giving high dielectric anisotropy value of a liquid crystal composition for TN display element containing the above-mentioned compound, and having wide liquid crystal temperature range and great anisotropy of refractive index. PREPARATION:A 4-(beta-alkoxyethoxy)-4'-cyanobiphenyl expressed by formula II is reacted with hydrogen chloride to give an imide ether derivative expressed by formula III, which is then reacted with ammonia to afford an amidine hydrochloride derivative expressed by formula IV. The resultant amidine hydrochloride derivative expressed by formula IV is then reacted with an acrolein derivative expressed by formula V to give the aimed compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel organic compounds, and more particularly to novel liquid crystal compounds useful as components of liquid crystal materials.

As is well known, liquid crystal compounds are used in various display devices by utilizing properties such as dielectric anisotropy and refractive index anisotropy in the liquid crystal phase. These displays are liquid crystal display elements that apply the electro-optic effect of liquid crystals, and some i are devices that apply the thermo-optic effect and other optical effects of liquid crystals. Together with advances in electronics, twisted nematic effects, guest・A large number of liquid crystal compounds are used in liquid crystal display devices that utilize electric field effects such as host effects.
Ru.

When these liquid crystal materials are used as individual compounds, their physical properties 1
For example, there is no material that can withstand practical use due to the liquid crystal temperature range, operating voltage, response performance, etc., and in practice, it is necessary to mix several types of liquid crystal compounds or non-liquid crystal compounds to obtain a material that can withstand use. I am in a situation where I am.

An object of the present invention is to provide a compound useful as a liquid crystal component constituting an FKT crystal composition that has excellent practical performance and is physically and chemically stable.

The present invention relates to 6-furkyl-2-(4-(
This is a liquid crystal composition containing β-alcopyrimidine and the compound.

The compound (I) of the present invention has a positive and significantly large galvanic anisotropy, a large refractive index anisotropy, and a wide liquid crystal temperature range, and also has heat, light, and temperature required as a raw material for a liquid crystal display. ,
It is a liquid crystal compound with excellent stability against electricity.

The compound of the present invention has good O compatibility with other liquid crystal compounds, so it can be used, for example, with bi7-enyl-based compounds, ester-based compounds, Schiff μ, and chitin carbon 1! It can be mixed with a liquid crystal composition consisting of several types of liquid crystal compounds such as phenyl ester type, phenylcyclohexane type, phenylmetadioxane type, and pyrimidine type.

The liquid crystal composition for TN display elements containing the compound of the present invention has excellent characteristics such as a large dielectric anisotropy value, a wide liquid crystal temperature range, and a wide anisotropy of the folded paper. ,
A liquid crystal display device using a cough liquid crystal composition can be used in a wide temperature range, and exhibits effects such as improved responsiveness, sharpness, and contrast.

The compound of the present invention can be synthesized according to the following reaction formula.

(In the formula, 11 or R2 represents an alkyl group having 1 to 10 carbon atoms.) First, 4-(β-fluoxyethoxy) +7-77 nobiphenyl (1) was reacted with hydrogen chloride gas in a 7-norcoal solvent. , to obtain an imide ether derivative (2).

Next, compound (1) is reacted with ammonia gas in an alcohol solvent to obtain a 7-midine hydrochloride derivative (conversion). Next, the compound (t) and the acrolein derivative (V) are combined with a suitable base catalyst (e.g., metal alcoholade, sodium hydroxide, l,8-cyazubicyclo(5,4,0)-7-
undecene, etc.), a condensation cyclization reaction is carried out to obtain the target compound (I).

The compounds of the present invention will be explained in detail with reference to Examples below.

Example 1 5-propyl-2-(4-(β-ethoxyethoxy)
+ 4'-biphenyl]pyrimidine anhydrous methanol lO
〇- Sodium hydroxide 2,5 f (0,06 mo
l) and dissolve 4-(β-ethoxyethoxy) ++
47-Piphenylylcampoquinamidine hydrochloride 10? (0
,03 mol) and 4.4 t (0.03 mol) of α-propyl-β-dimethylaminoacidol. After boiling for 2 hours while stirring with a filter, methanol was distilled off. Add 200 mg of water and 20 mg of toluene to the reaction residue.
The product was extracted into a toluene layer, the extract was washed with water, the toluene was distilled off, and the remaining solid was recrystallized three times with ethanol to obtain 5-7' E-pil-2.
-(4-(β-ethoxyethoxy)-4'-biphenylyl)pyrimidine 62 (αo2 mol) was obtained.

The elemental analysis values of this compound were in good agreement with the theoretical values as shown below.

Moreover, the phase transition point of this compound was as follows. The crystal-nematic phase transition point (hereinafter abbreviated as C-N point) is:
116°C, nematic-isotropic liquid phase transition point (hereinafter referred to as N-I
(abbreviated as point) was 184°C.

Examples 2 to 6 Table 1 shows metal compounds of formula (1) synthesized by a method similar to Example 1 and their phase transition points.

Here, the crystal phase is abbreviated as C, the smectic phase as S, the nematic phase as N, and the isotropic liquid phase as I, and the mark in the lower column indicates the presence of the above phases.

Table 1 Example F (Application example) The N-1 point of the liquid crystal composition (A) is 52.1°C,
The viscosity η3o at 20°C is 23.4 cP, the dielectric anisotropy Δε is 11.2 (ε1 mouth 15.9, εi bow 7), and when this is sealed in a TN cell with a cell thickness of 1 μm, the threshold voltage is 1 .54V, the saturation voltage is 2.13V,
The refractive index anisotropy Δn is 0.119 (n・-1,609,
noml, 490).

One portion of the compound 5-propyl-2-(4-(β-ethoxyethoxy)++41-biphenylyl)pyrimidine shown in Example 1 of the present invention was added to 85 parts by weight of the liquid crystal compound (4).
The N-1 point of the liquid crystal composition to which 1 part of 51ff was added was 64.4°C.
, Ri2o is 30.4 aP, and Δε is 11
．． 7 (a, -16,9, C -5,2), and when this is sealed in the same TN cell, the threshold voltage is 1.59'l/, and the saturation voltage is 2.2fV. and Δ
nu Q, 133 (ms-1,629, noml, 4
96).

that's all

Claims (2)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1 or R^2 represents an alkyl group having 1 to 10 carbon atoms.) 5-alkyl-2-[4 −
(β-alkoxyethoxy)-4'-biphenylyl]pyrimidine. (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1 or R^2 represents an alkyl group having 1 to 10 carbon atoms.) 5-alkyl-2-[4 −
A liquid crystal composition containing at least one type of (β-alkoxyethoxy)-4'-biphenylyl]pyrimidine.