JPS61291536A - Crotyloxybenzene derivative - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [R is 1-9C n-alkyl; the ring A is cyclohexane ring or group of formula V; the cyclohexane ring has trans (equatrial-equatrial) configuration; crotyl group has transconfiguration]. USE:An electro-optical displaying material. It has excellent high speed response or steep transmittance-voltage characteristics and relatively high N-I transition temperature. It can be used as a material for dynamic light-scattering display cell by mixing with other nematic liquid crystal compound or as a material for field effect display cell. PREPARATION:The compound of formula I can be produced by reacting the compound of formula II with an alkali such as KOH in an organic solvent such as ethanol and reacting the resultant phenolate with trans-crotyl chloride of formula III.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to novel rotyloxybenzene derivatives useful as electro-optic display materials.

[Conventional technology]

M-Shut (M-8) is a typical liquid crystal display cell.
ehadt) etc. (APPLIED pHYsIcs
LETTERS Dan 127-128 (1971), nine field-effect mode cells or G-H Heilmeler et al. (PROCEEDI)
NG OF THE 1. E, E, E.

561162-1171 (1968): Dynamic scattering mode cell proposed by l K or CAPPIJED such as G-H Beilmeyer (G-HH*11m5ier) etc.
PHYSIC8LETTER8tan91 (1968)) or D L White
) etc. (JOURNAL OF APPLIED PHYS
There is a dust host type cell proposed by IC 845, 4718 (1974).

Among these liquid crystal display cells, field effect cells are particularly excellent and are currently widely used. Field-effect cells are required to have various characteristics, and high-speed response and steep transmittance-voltage characteristics are important characteristics required for producing a TN-LCD with a large amount of information. Currently, nematic liquid crystal materials for high-speed response have low viscosity. ) is useful, and has a steep transmittance-voltage characteristic.
11 values (spray K) are each known to be useful.

The excellent properties of these compounds (low viscosity and stiffness).In general, most of the liquid crystal materials that can be used for practical purposes usually consist of a compound that has a nematic phase near room temperature and a compound that has a nematic phase at a temperature higher than room temperature. prepared by mixing seeds or more ingredients.Currently T
Many of the mixed liquid crystals practically used for N-LCD production are required to have a nematic phase over the entire temperature range of at least -30°C to +65°C.

Therefore, in order to increase the N-I transition temperature, N-I transition is usually applied to a liquid crystal compound containing a compound (b) with excellent high-speed response or a compound (b) with steep transmittance-voltage characteristics. A mixture of liquid crystal compounds having three high-temperature rings is used. However, although the N-I transition temperature increases by mixing a compound having three rings, a compound having the (&) compound or the (b) compound and having a high N-I transition temperature has been desired.

[Problem that the invention seeks to solve]

An object of the present invention is to provide a compound that has excellent high-speed response or steep transmittance-voltage characteristics, and has a relatively high N-I transition temperature.

[Rounding method to solve problems]

The present invention solves the above problems by providing a compound represented by the general formula:

The compound of formula (1) according to the present invention can be produced according to the following production method. However, if the following formula (In is replaced by the formula (I
The compound of F) is reacted with an alkali such as potassium hydroxide in an organic solvent such as ethanol to form a phenolate;
This is reacted with trans-crotyl chloride to produce a compound of formula (1).

Table 1 lists the transition temperatures of representative compounds of formula (1) thus produced.

From the data posted in Table 1, the N of the compound A1 of the present invention
-I transition temperature is 58°C and the corresponding formulas c, a, (28
The N-I transition temperature of ρ)-QC4H is 32℃, and that of ρ) is 26℃.
expensive. The N-I transition temperature of the compound of &2 is 61°C, which is 8°C higher than the N-I transition temperature of the corresponding compound of 2〇 bHls < large DOC4H, which is 53°C.

As described above, it can be seen that the compound of the present invention has a higher N-I transition temperature than the known nematic liquid crystal compound (compound of formula R4u') which has excellent properties.

The compound of formula (1) according to the present invention can be used in a mixture with other nematic liquid crystal compounds as a material for a dynamic light scattering display cell or as a material for a field effect display cell.

Thus, preferred representative examples which can be used in admixture with compounds of formula (I) include, for example, 4.4'-substituted benzoic acid phenyl ester, 4.4'-substituted cyclohexane carmenic acid phenyl ester, 4.4'-substituted cyclohexanecarmenic acid phenyl ester, .4'-substituted cyclohexane carmenic acid biphenyl ester, 4(4
-Substituted cyclohexanecaryloxy)benzoic acid 4'
-Substituted phenyl ester 4 (4-substituted cyclohexyl)
Benzoic acid 4'-substituted phenyl ester, 4(4-substituted cyclohexyl)benzoic acid 4'-substituted cyclohexyl ester, 4,4'-substituted biphenyl, 4,4'-substituted phenylcyclohexane, 4,4'-directly substituted ter phenyl, 4
, 4'-biphenylcyclohexane, 2 ('i' -
Examples include 5-f-substituted pyrimidine (phenyl) and 5-f-substituted pyrimidine.

〔Example〕

Example 1 Compound 4.7.9 (0,0
22mob) was dissolved in ethanol 33+t, and 85
After adding 1.511% (0,023 mot) of potassium hydroxide, 2.21 (0,024 mot) of trans-crotyl chloride was added dropwise at reflux temperature while stirring, and the mixture was further reacted at the same temperature for 5 hours. . After cooling, water was added to the reaction mixture, the reaction product was extracted with ether, the extract was washed with water, and after drying, the ether was distilled off from this liquid.

The obtained reaction product was purified by recrystallization from ethanol to obtain the following compound 4.51 (0,017 mot).

Yield 7712 Transition temperature 43°C (C-+N) 58°C (N#I) Example 2 Formula n-c 6H1,%H'' Compound 10.01!(0,0
391m6t) Dissolved in 70m/pnol,
85% potassium hydroxide 2.81 (0,043mol)
3.911 (0,043 mot) of trans-crotyl chloride was added dropwise to the mixture at reflux temperature while stirring, and the mixture was further reacted at the same temperature for 7 hours. After cooling, water was added to the reaction mixture, the reaction product was extracted with ether, the extract was washed with water, and after drying, the ether was distilled off from this liquid.

The obtained nine reaction products were purified by recrystallization from ethanol to obtain the following compound 9.41 (0,030 mot).

Yield: 77% Transition temperature: 54°C (C-+N) 61°C (N=I) [Effects of the invention] The compound of formula (1) according to the present invention has a higher N-I than the conventionally known crystalline compound 2. It is a compound that has steep transmittance-voltage characteristics due to liquid crystallization with a high transition temperature, or excellent high-speed response due to having a % skeleton.

Claims (1)

[Claims] General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R represents a linear alkyl group having 1 to 9 carbon atoms, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , cyclohexane ring, or ▲Mathematical formulas, chemical formulas, tables, etc.▼
, the cyclohexane ring has a trans (equatorial-equatorial) configuration, and the crotyl group has a trans configuration. ] A compound represented by