JPS5849325A - 1-cyclohexyl-2-(4'-halophenyl)ethane derivative - Google Patents

Abstract

NEW MATERIAL:The 1-[trans(equatorial-equatorial)-4'-n-alkylcyclohexyl]-2-(4''- halophenyl)ethane of formulaI(R is 1-7C straight-chain alkyl; X is halogen). USE:The displaying material of a liquid crystal display element for electronic calculator, wrist watch, etc. It has high nematic-isotropic transition temperature and low viscosity. It has extermely high chemical stability, does not decompose by water, light, etc., and has colorless milk white appearance. A rapid responce liquid crystal display element having long life and broad nematic temperature range can be produced from the compound. PROCESS:The compound of for formulaIcan be prepared by reacting a halophenyl with the compound of formula II and anhydrous sluminum chloride in carbon disulfide or nitrobenzene, and reacting the resultant compound of formula III with hydrazine and potassium hydroxide in diethylene glycol or triethylene glycol.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel nematic liquid crystal compounds of cyclohexylphenylethane derivatives useful as electro-optic display materials. The nematic liquid crystal provided by the present invention is 1
- 1-(trans(equatorial-equatorial)-4'-n-alkylcyclohexyl)-2-(
The compound 4'-7-lorophenyl)ethane-(-A6゜fu) is a compound with weak positive U* anisotropy, such as M-8chadt (
APPLIED PHYSICB LETTER81B
127-12B (1971)) or the field effect mode cell proposed by G.H.
1m*i@r') etc. [PRO(JEDING OF
THEI EJl, E, 56 1162-1171
(196B)) or the dynamic scattering mode cell proposed by G. H. Beilmeyer (G-HHei1mei@r) [:APP
LIED PHYSIC8LETTER8, i! , 91
(1968)) Now D L White (D
L White ) etc. (JOURNAL OF AP
PLIED PHYSIC 8th, 471B (1974))
It can be applied to the guest-host type cell proposed by

The compound of Tsukasa I) is characterized by a high nematic-isotropic liquid transition temperature and low viscosity, and is also chemically very stable and does not decompose due to moisture, light, etc.
Naturally nothing.

It has many excellent properties such as a milky white color. Therefore, by using the compound of Tsukasa I), it is possible to produce a liquid crystal display element with a long life, a wide nematic temperature range, and a high speed response.

According to the present invention, the compound of formula (1) is produced according to the following production method.

1st step - The halolobiphenyl is diwaxed or reacted with the present compound in nidobenzene to produce the compound 2〇IN).

Second step - The compound of 2Ql[) produced in the first step is reacted with hydrazine and potassium hydroxide in diethylene glycol or triethylene glycol to form the formula (1).
Manufacture the compound.

The transition temperature of the compound of formula (1) thus produced is
Listed in the table.

Table 1 RX Transition temperature <'C) n-C, H, -F 5 (C-4I) -2
5(1,:!N)n CaH,F7(C-4I
) 2 B (IIN)n-C, fan-F
9 (C-+I)-8(raN) In the table, C represents a crystal, N represents a nematic phase, and I represents an isotropic liquid.

When used as a display element material for calculators, wristwatches, and other devices, the compound of formula (1) may be in the form of a mixture of 211 or more of the compounds, or one type of the compound or 2811 or more of the compounds and other nematic liquid crystal compounds and/or Although it can be used in the form of a mixture with a non-nematic liquid crystal compound, preferably, a mixture of two or more compounds of formula (1) is used as a matrix liquid crystal, and this matrix liquid crystal is combined with other nematic liquid crystal compounds and/or Alternatively, it is recommended to use a mixture of non-nematic liquid crystal compounds. Other nematic liquid crystal compounds and/or non-nematic liquid crystal compounds that can be used in combination with the compound of formula (1) include nematic liquid crystal compounds with large positive dielectric constant anisotropy (hereinafter referred to as Np-type liquid crystal); and/or non-nematic liquid crystal compounds that are homologs of Np-type liquid crystals (hereinafter referred to as Np-type liquid crystal homologs), nematic liquid crystal compounds having negative or small positive dielectric constant anisotropy (hereinafter referred to as N! & type liquid crystals); Also included are non-nematic liquid crystal compounds that are homologs of Nn-type liquid crystals (hereinafter referred to as Nn-type liquid crystal homologs), and mixtures thereof.

Preferred specific examples of Np-type liquid crystals and Np-type liquid crystal homologues that can be used in combination with the compound (I) are listed below.

6- In the formula, 8 is n -CmHlm-1-, -1n-Cm%m
Represents either +1-0- (where m is an integer from 1 to 10).

In the formula, R is n-CmH, m4-1m4-1-1n-C+
, -0- (where m is an integer from 1 to 8).

In the formula, R represents n-CmHl·n++1- (however,
m is an integer from 1 to 10).

In the formula, R is n−C哄m+@−1n −CmH1m4, −
It represents either 0-n-Cml or m4-, -8-0- (where m is an integer from 1 to 10).

In the formula, R represents - in nl to n-Cm1 (however, m
is an integer from 1 to 8).

In the formula, R is m' CrnHlm + 5-1n -Cm
Hlm +t -0- (where m is an integer from 1 to 10).

In the formula, R is n-CnaH1m41-1n-CmH,m
Represents either + or -0- (where m is an integer from 1 to B).

In the formula, R represents H-CmHlm + s- (however,
m is an integer from 1 to 10).

In the formula, 8 represents n-CmI (1m+1-, X is F,
Represents either CI or Br11 (where m is 1 to 8
integer).

In the formula, R represents n-CmH1m+t- (however, m is an integer from 1 to 10).

In the formula, R and R' are respectively n-CtaH, m4. - (where m is an lI number from 1 to 5).

'In the formula, R represents n-C111+t- (however, m
is an integer from 1 to 10).

In the formula, R represents n-Cm1 or In+t- (however, 1m
is an integer from 1 to 10).

In the formula, R is ys-CmH! m4-1- (however,
m is 1-100IB).

Next, preferred specific examples of Nn-type liquid crystals and Nu-type liquid crystal analogs that can be used in combination with the compound of formula (1) are listed.

-15: “In the form of a mixture of two or more compounds of formula (1) or in the form of a mixture of two or more compounds of formula (1)
) can be used as a liquid crystal for a DSM cell in the form of a mixture of one or more of the above compounds and the above-mentioned Nn-type liquid crystal and/or its homolog.

In addition, a liquid for FEM cells may be used in the form of a mixture of one or more of the compounds of formula (1), the above-mentioned Np-type liquid crystal and/or its homologue, and the above-mentioned Nn-type liquid crystal and/or its homologue. Can be used by mouth.

Next, the present invention will be specifically explained using examples.

In an example, 16.1 d of anhydrous aluminum chloride (
(1120 mol) was added thereto, and trans=4-n-globylcyclohexyl acetic acid chloride 2[L3,9 (α100 mol) was added dropwise while stirring at room temperature. This is 1
Cool to 0°C and stir until p-fluorobenzene! 6J
i' (Q, 100 mol) was gradually added dropwise to the mixture and reacted at 10°C for 5 hours, then returned to room temperature and reacted for 2 hours. After the reaction, carbon disulfide was distilled off, and the mixture was added to ice water and stirred at 60°C for 1 hour. After cooling, it is extracted with ether, washed with water, dried, and after distilling off the ether, it is vacuum distilled to obtain the following compound 18. IJF (0,0691mo
l) was obtained.

This compound contains triethylene glycol 1ooy, so%
Hydrazine hydride 12.1g (0,193mol
), 85% potassium hydroxide 22. GI ([1346m
ol) and gradually raise the temperature to 150°C while stirring.
The mixture was allowed to react for 3 hours.

After cooling, 150ml of water was added and extracted with n-hexane.

After washing with water and drying over anhydrous sodium sulfate, n-hexane was distilled off and purified by vacuum distillation to obtain 152 g of the following compound (
α0532 mol) was obtained.

15- Yield 5'5.2% Transition temperature 5℃ (C→■)
-25°C (tpN) Example 2 The following compound was obtained in the same manner as in Example 1.

Yield: 57.1% Transition temperature: 9°C (C → Engineering) -
8°C (x+!N) Example 6 Same I! as Example 1! The following compound was obtained in a conventional manner.

Yield 55.8% Transition temperature 7°C (C-+I)
-28℃ (IRN)

Claims (1)

[Claims] A compound represented by