JPH03145450A - Phenylacetylene compound - Google Patents

Abstract

NEW MATERIAL:A phenylacetylene compound expressed by formula I[R<1> and R<2> are 1-10C alkyl or alkoxy; A, Y and Z each are independently 1,4-phenylene (one or two CH groups present in the group may be substituted with N and one or two H present in the group may be substituted with F) or trans-1,4- cyclohexylene; B is -COO-, -OCO-, CH2O-, -O-CH2 or -CH2CH2-; W is -CH2CH2-; k, l, m and n are 0 or 1]. EXAMPLE:1-(3-Cyano-4-ethoxy)-2-(4-propylphenyl)acetylene. USE:Useful as a liquid crystal for liquid crystal display elements and excellent in compatibility with itself or other liquid crystalline compounds. PREPARATION:An acetylene derivative expressed by formula II is reacted with a compound expressed by formula III (X is CL or Br) to provide a compound expressed by formula IV, which is then reacted with a cyaogenating agent in a polar aprotic solvent. The produced complex is then decomposed to afford the compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a novel liquid crystal compound useful for liquid crystal display elements and a liquid crystal composition containing the compound.

(Prior Art) Display devices using liquid crystals utilize electro-optical effects based on the anisotropy of dielectric constant and electrical conductivity of liquid crystal substances.

Liquid crystal display methods include dynamic scattering type (DS type), twisted nematic type (TN type), super twisted nematic type (STN type), phase change type (PC type), and electric field controlled birefringence type (ECB type). There are various methods such as , guest-host type (GH type).

The ECB type was announced in 1971 (M, 5chiek
el and, Fahrenschon+ ^p
p1. Phys, Lett, 19 (197
1) 391"), it has gained attention as a display method that has the potential to increase the capacity of high-quality black and white displays using simple matrix drive. Along with this, liquid crystals with negative dielectric index anisotropy have been used. Demands for compositions are increasing.

This is because the response speed is inversely proportional to the square of the cell thickness, so Δ
This is because the larger n is, the thinner the cell thickness can be, which is advantageous for improving response speed.

Currently, there is no single compound that satisfies all of these requirements, and in fact, liquid crystal compositions obtained by mixing several types of liquid crystal compounds are used.

Known compounds that have been developed so far and have a negative Δε include those that have a 2,3-dicyanophenyl group in their molecular structure, cyclohexane derivatives that have a cyano group in the axial position, and pyridazine derivatives. Are known. For example, a compound having a 2,3-dicyanophenyl group in its molecular structure (Japanese Unexamined Patent Publication No. 10557/1983)
Although it has the advantage of having a large negative Δe, it has the disadvantage of poor solubility and high viscosity, and it is also a cyclohexane derivative having a cyano group at the axial position (R.

Eidenschink, G., Baas, M.
Romer, B., 5cheubj2e.

Angew, Chem, 96 (1984) 151
．． ) does not have a very large negative Δε, despite having a molecular structure with a cyano group in the short axis direction of the molecule. and pyridazine derivatives (JP-A-59-1064)
Most of them do not have a liquid crystal phase, and when mixed with other liquid crystal compounds, the disadvantage is that the clearing point of the liquid crystal phase decreases.

And these series of compounds have a somewhat large negative Δε
However, it does not have a large Δn in general.

(Objective of the Invention) An object of the present invention is to provide a liquid crystalline compound having a large Δn and a negatively large Δε and having excellent compatibility with itself or with other liquid crystalline compounds.

(Structure of the Invention) That is, the present invention provides - formula % formula % (1) (In the formula (f), R1 and R2 each independently represent an alkyl group or an alkoxy group having 1 to 10 carbon atoms, and A
, Y, Z are each independently 1,4-phenylene (one or two C present in this group) I group may be replaced with N, and one or two C present in this group (H may be replaced with F) or trans-C4-cyclohexylene, B is -COO-,
-0CO-, -CIltO-, -0-CIl□- or -C1(ICH!-), W indicates -CH, C1,-, and k, l, m, and n are each independently 0 or 1. A liquid crystal composition containing a phenylacetylene compound represented by the following formula and at least one thereof.

(Actions and Effects of the Invention) The compound (1) (2) of the present invention can be used as a constituent component of a liquid crystal composition for a liquid crystal display element based on a DS type, TN type, STN type, DC type, ECB type, or GH type. can be done, but
The compound of formula (1) is characterized by having a relatively large Δn and a relatively large Δε, so it can be particularly suitably used as a component of a liquid crystal composition for a display element based on the ECB type.

The compound represented by formula (1) has a wide range of uses as a liquid crystal for liquid crystal elements, and by selecting its substituent, it can be added to a liquid crystal composition consisting of other compounds to improve the Δε of the liquid crystal composition.
and Δn can be set to a preferable value.

The compound represented by the formula (N is colorless in its pure state,
Many of these compounds have a liquid crystal phase in a temperature range suitable for use as a display element, and these compounds are extremely stable against chemical, thermal, or light effects.

The compound represented by formula (I) has the following partial formulas (Ia) to (
Compounds represented by Ii) are included.

CN Among these, sub-formulas (Ia), (Ib), (I
Particularly preferred are compounds represented by c) and (Ig).

The compound represented by sub-formula (Ia) further includes preferred compounds represented by sub-formulas (Iaa) to (lad) below.

CN (Phe is 1,4-phenylene unsubstituted or having one or more F atoms as a substituent, Cy
C is trans-1,4-cyclohexylene, Py
d represents pyridine-2,5-diyl and Pyr represents pyrimidine-2,5-diyl. The same applies hereinafter) The compound represented by the partial formula (Ib) further includes preferred compounds represented by the following partial formulas (I ba) to (I bl).

C.N. Subexpression (1 ) The compound represented by Further below subexpression of () %formula%) preferred indicated by Compounds included.

Compounds included.

CN In each of the above formulas, R1 and R2 are linear or branched alkyl groups or alkoxy groups, preferably linear alkyl groups or alkoxy groups having 1 to 8 carbon atoms, particularly preferably carbon atoms. It is a linear alkyl group having 2 to 7 numbers.

Compounds of formula (1) with branched R1, RZ have improved solubility in customary liquid crystal substrates and are therefore important in some cases, especially when they are optically active. It is important as a doping agent. Branched groups of this type generally have one chain branch.

The liquid crystal composition of the present invention contains 2 to 25 types, preferably 3 to 15 types, containing at least one type of compound represented by 2N).
Consists of seeds. Components other than the compounds of formula (I) include nematic substances, in particular azoxybenzene compounds, benzylideneaniline compounds, biphenyl compounds, terphenyl compounds, phenyl or cyclohexylbenzoate compounds, phenyl or cyclohexylcyclohexanecarboxylate compounds, phenyl Cyclohexane compound, cyclohexyl biphenyl compound, cyclohexylcyclohexane compound, cyclohexylnaphthalene compound, 1.4-biscyclohexylbenzene compound, 4.4'-biscyclohexylbiphenyl compound,
Phenylpyrimidine compounds or cyclohexylpyrimidine compounds, phenylpyridazine compounds or cyclohexylpyridazine compounds and their N-oxide compounds, phenyldioxane compounds or cyclohexyldioxane compounds, phenyl-1,3-dithiane compounds or cyclohexyl-1,3- dithiane compound, 1.2-
diphenylethane compounds, ■-phenyl-2-cyclohexylethane compounds, 1,2-dicyclohexylethane compounds, optionally 10genated stilbene compounds, benzylphenyl ether compounds, tolan compounds, and substituted cinnamic acid compounds. It is preferable to select from known substances belonging to the group.

The composition according to the present invention comprises one of the compounds represented by formula (1).
Contains the species or species in an amount of about 0.1 to 40% by weight. More preferably, one of the compounds represented by formula (1)
The species or species are contained in an amount of 10 to 300 to 30 by weight.

The compositions according to the invention are manufactured in a manner customary per se. Generally, the components are dissolved in each other, preferably at elevated temperatures.

(Production method of compound) An example of the method for producing the compound of the present invention is shown by the following formula.

(It) R”-(Z),-(Ka),-Y-CmiC) I(IV) Pd [PPt+3) zcl z, Cu1
Et NH (Vl) (In the above formula, R', R'', A, B, Y, W, Zk
, l, m and n are the same as above, and X represents cl or Br. ) That is, the method known from aldehyde derivative (II) (
J, Villieras, p, Perriot+
J, F, Nor+aant.

5ynthesis (1975) 458) to dichloroolefin (1), acetylene derivative (
IV) and to which the iodide (V) is treated with a palladium catalyst (e.g.
bistriphenylphosphine palladium dichloride) and copper iodide according to the literature method (Tetrah
edron Letters, 50 (1975)
4467) to obtain halo-substituted phenylacetylene derivative 4 (Vl), to which N-methyl-2-
A cyanating agent such as copper cyanide, sodium cyanide, potassium cyanide is reacted in a polar aprotic solvent such as pyrrolidone, DMF, DMSO, or HMP, and the resulting complex is decomposed with iron chloride, ethylenediamine, etc. The desired compound (1) can be obtained by purification using a conventional method.

(Examples) Hereinafter, the present invention will be explained in more detail with reference to specific examples.

In the examples, the "rN-1 point" refers to the "nematic phase-isotropic liquid phase transition point".

Example 1 (Production of 1-(3-cyano-4-ethoxy)-2-(4-propylphenyl)acetylene) 29.9 g (0,091 mol) of 3-bromo-4-ethoxyiodobenzene
was dissolved in 100 mt' of diethylamine. Under a nitrogen gas flow, 0.96 g of dichlorobistriphenylphosphine palladium (II) and 0.52 g of cuprous iodide
g and stirred at room temperature for about 30 minutes. To this solution, add 13.2 g of 4-propylphenylacetylene to n-
The reaction temperature was 30℃.
was added at a rate that did not exceed . Thereafter, the mixture was stirred and reacted at room temperature for 20 hours. 300 ml of water was added to the reaction mixture, and the liberated oil was extracted with 50 l of raw butane. The extract was washed with dilute hydrochloric acid, a dilute aqueous alkaline solution, and then water until the washing solution became neutral, and then dried over anhydrous sodium sulfate. After this, the n-hebutane solution was filtered off and the n-hebutane solution was filtered off.
Hebutane was distilled off, and the resulting concentrated residue was distilled under reduced pressure (bp220'C7'3.5 steel-11g) 1
5.0 g of crude target product was obtained. This is 40mj! of ethyl alcohol to give 13.3 g of 1-(3-
Bromo-4-ethoxyphenyl)-2-(4-propylphenyl)acetylene was obtained. Melting point: 81.7°C. This is 100m7! of N-methyl-2-pyrrolidone and cyanide HPf5. Og was added and the mixture was reacted under reflux for 10 hours. After the reaction is complete, add 8.8g of iron chloride to the reaction solution.
A solution prepared by dissolving 50 II of water and 7 ml of concentrated hydrochloric acid was added thereto, and the mixture was heated and stirred at 60° C. for 1 hour. After that, the reaction solution was added to 300 ml of water, and the liberated oil was mixed with 1 ml of toluene.
Extracted with OOra1. The extract was washed with water, the toluene layer was dried over anhydrous sodium sulfate, and the toluene was distilled off. The fractions showing a single spot on TLC were collected and concentrated, and the residue was recrystallized from ethyl alcohol to obtain 1-(3-cyano-4-ethoxyphenyl') of 6.58. -2-(4-propylphenyl)acetylene (compound number 1) was obtained.

The melting point of this product was 93.9°C, Δε obtained by extrapolation was -4.2, and Δn obtained by extrapolation was 0.198, which was a very large value.

The following compounds are produced in the same manner.

(Compound 2) l-(3-cyano-4-propoxyphenyl')-2-(4-butylphenyl)acetylene, (Compound 3) l-(3-cyano-4-butyloxyphenyl')-2 -(4-ethylphenyl)acetylene, (Compound 4) 1- (3-cyano-4-ethylphenyl)-2-(4-butylphenyl)acetylene, (Compound N15) 1- (3-cyano-4- propylphenyl)-2-(4-propylphenyl)acetylene, (compound N116)1- (3-cyano-4-butylphenyl)-2-(4-ethylphenyl)acetylene, (compound Il&17)1- (2- Cyano-4-ethoxyphenyl)-2-(4-butylphenyl)acetylene, (Compound NL18) l-(2-cyano-4-propoxyphenyl)-2-(4-propylphenyl)acetylene, (Compound 9) l-(2-cyano-4-butyloxyphenyl)-2-(4-ethylphenyl)acetylene, (Compound 10) 1-(2-cyano-4-ethylphenyl)-2-(4-7'tylphenyl ) acetylene, (compound 1'& L11) 1- (2-cyano-4-
(compound 11h12) 1-(2-cyano-4-butylphenyl)-2-(4-ethylphenyl)acetylene.

Example 2 According to the method of Example 1, the corresponding 3-bromo-4-ethoxydhenase: /29.9 g (0,091 mol) and 21.8 g of 4-(4-butylcyclohexyl)phenylacetylene 1-(3-bromo-4-
Ethoxyphenyl)-2-(4-(4-butylcyclohexyl)phenyl)acetylene was obtained, which was cyanated according to the method of Example 1 and purified by a conventional method to obtain 8.8
g of 1-(3-cyano-4-ethoxyphenyl)-2
-(4(4-butylcyclohexyl)phenyl)acetylene (compound 1tl 3) was obtained.

The following compounds are produced in the same manner.

(Compound 14) 1-(3-cyano-4-propoxyphenyl)-2-(4-(4-propylcyclohexyl)
phenyl)acetylene, (compound 11h15) 1-
(3-cyano-4-butyloxyphenyl)-2-(
4-(4-ethylcyclohexyl)phenyl)acetylene, (compound 11h16) l-(3-cyano-4-
ethylphenyl)-2-(4-(4-butylcyclohexyl)phenyl)acetylene, (Compound N117) 1-(3-cyano-4-propylphenyl)-2-(4-(4-propylcyclohexyl)phenyl)acetylene , (compound ll & 1lB) 1- (3-cyano-4-
butylphenyl)-2-(4-(4-ethylcyclohexyl)phenyl)acetylene, (Compound 19) 1-(2-cyano-4-ethoxyphenyl)-2-(4-(4-butylcyclohexyl)phenyl) Acetylene, (Compound 20) 1-(2-cyano-4-propoxyphenyl)-2-(4-(4-propylcyclohexyl)
phenyl)acetylene, (compound number 21) 1-(2-cyano-4-butyloxyphenyl)-2-(4-(4-
Ethylcyclohexyl)phenyl)acetylene, (Compound 11h22) l -(2-cyano-4-ethylphenyl)-2-(4-(4-butylcyclohexyl)phenyl)acetylene, (Compound 23) 1-(2-cyano -4-propylphenyl)-2-(4-(4-propylcyclohexyl)phenyl)acetylene, (Compound Light 24) 1-(2-cyano-4-butylphenyl")-2-(4-(4-ethyl) cyclohexyl)phenyl)acetylene.

Example 3 Following the method of Example 1, 29.9 g (0,091 mol) of the corresponding 3-bromo-4-ethoxyiodobenzene and 21.9 g (0,091 mol) of 4-(2-(4-butylcyclohexyl)ethyl)phenylacetylene were prepared. 8g of 1-(3-
Bromo-4-ethoxyphenyl)-2-(4-(2-(
4-Butylcyclohexyl)ethyl)phenyl)acetylene was obtained. It was cyanated according to the method of Example 1, and purified by a conventional method to produce 9.2 g of 1-(3-cyano-
4-ethoxyphenyl)-2-(4-(2-(4-butylcyclohexyl)ethyl)phenyl)acetylene (Compound No. 25) was obtained.

The following compounds are produced in the same manner.

(Compound 26) 1-(3-cyano-4-propoxyphenyl)-2-(4-(2-(4-propylcyclohexyl)ethyl)phenyl)acetylene, (Compound 27) 1-(3-cyano- 4-Butyloxyphenyl)-2-(4-(2-(4-ethylcyclohexyl)ethyl)phenyl)acetylene, (Compound Light 28) 1-(3-cyano-4-ethylphenyl)-2-(4- (2-(4-butylcyclohexyl)
Ethyl)phenyl)acetylene, (Compound 29) 1-(3-cyano-4-propylphenyl)-2-(4-(2-(4-propylcyclohexyl)ethyl)phenyl)acetylene, (Compound 1'h30) l-(3-cyano-4-butylphenyl")-2-(4-(2-(4-ethylcyclohexyl)ethyl)phenyl)acetylene, (Combination beginning 31) l-(2-cyano-4-ethoxy phenyl)-2-(4-(2-(4-butylcyclohexyl)ethylronphenyl)acetylene, (Compound Il&132) 1-(2-cyano-4-
propoxyphenyl)-2-(4-(2-(4-propylcyclohexyl)ethyl)phenyl)acetylene, (compound+lyJ floor 33) 1-(2-cyano-4-butyloxyphenyl)-2-(4-( 2-(4-ethylcyclohexyl)ethyl)phenyl)acetylene, (compound 1'h34) 1-(2-cyano-4-ethylphenyl)-2-(4-(2-(4-butylcyclohexyl)ethyl)phenyl ) Acetylene, (Compound 35) 1-(2-cyano-4-propylphenyl') -2-(4-(2-(4-propylcyclohexyl)ethyl)phenyl)acetylene, (Compound 36) 1-( 2-cyano-4-butylphenyl)-2-(4-(2-(4-ethylcyclohexyl)
Ethyl) phenyl) acetylene.

Example 4 According to the method of Example 1, 29.9 g (0,091 mol) of the corresponding 3-bromo-4-ethoxyiodobenzene and 21.9 g of 4-butylbiphenyl-4'-acetylene were prepared.
g to obtain L-(3-bromo-4-ethoxyphenyl)-2-(4'-butylbiphenyl-4-yl)acetylene.

They were cyanated according to the method of Example 1, and purified by a conventional method to obtain 7.2 g of 1-(3-cyano-4-ethoxyphenyl)-2-(4'-butylbiphenyl-4-yl). ) Acetylene (Compound Hikari 37) was obtained.

The following compounds are produced in the same manner.

(Compound 38) 1-(3-cyano-4-propoxyphenyl)-2-(4'-propylbiphenyl-4-yl)acetylene, (Compound 39) 1-(3-cyano-4-butyloxyphenyl) )-2-(4'-ethylbiphenyl-4-yl)acetylene, (Compound 40)1-(3-cyano-4-ethylphenyl)-2-(4'-butylbiphenyl-4-yl)
Acetylene, (Compound NQ41) 1-(3-cyano-4-propylphenyl)-2-(4'-propylbiphenyl-4
-yl)acetylene, (compound IVk142) 1-(3-cyano-4-
butylphenyl)-2-(4'-ethylbiphenyl-4
-yl) acetylene, (Compound Magnetism 43) 1-(2-cyano-4-ethoxyphenyl)-2-(4'-butylbiphenyl-4-yl)acetylene, (Compound Nl144) 1-(2-cyano- 4-propoxyphenyl') -2-(4'-propylbiphenyl-4-yl)acetylene, (Compound 45) 1-(2-cyano-4-butyloxyphenyl)-2-(4'-ethylbiphenyl- 4-yl)acetylene, (Compound 11h46) 1-(2-cyano-4-ethylphenyl)-2-(4'-7" tylbiphenyl-4-yl)acetylene, (Compound 47) L-(2- Cyano-4-propylphenyl)-2-(4'-propylbiphenyl-4-yl)
Acetylene, (Compound Magnetism 48) 1-(2-cyano-4-butylphenyl)-2-(4'-ethylbiphenyl 4-yl)acetylene.

Example 5 The corresponding 3-bromo-4-(4
-ethylcyclohexylcarbonyloxy)-1-iodobenzene (21.84 g (0.05 mol)) and 4-butylphenylacetylene (7.9 g) were reacted.
Bromo-4-(4-ethylcyclohexylcarbonyloxy)phenyl)-2-(4-butylphenyl)acetylene was obtained. It was cyanated according to the method of Example I and purified by a conventional method to produce 5.9 g of 1-(3-cyano-
4(4-ethylcyclohexylcarbonyloxy)phenyl')-2-(4-butylphenyl)acetylene (compound 49) was obtained.

The following compounds are produced in the same manner.

(Compound 11h50) 1- (3-cyano-4-(
4-Propylcyclohexylcarbonyloxy)phenyl)-2-(4-propylphenyl)acetylene, (Compound lI&L51) 1-(3-cyano-4-(
4-butylcyclohexylcarbonyloxy)phenyl)-2-(4-ethylphenyl)acetylene, (Compound Kinetic 52) 1-(2-cyano-4-(4-ethylcyclohexylcarbonyloxy)phenyl)-2-(
4-Butylphenyl)acetylene, (Compound Magnetism 53) 1-(2-cyano-4-(4-propylcyclohexylcarbonyloxy)phenyl)-2-
(4-propylphenyl)acetylene, (compound magnetism 54) 1-(2-cyano-4-(4-butylcyclohexylcarbonyloxy)phenylene-2-(4
-ethylphenyl)acetylene.

Example 6 The corresponding 3-bromo4-(4-
ethylbenzoyloxy)-1-iodobenzene21.
5 g (0.05 mol) and 7.9 g of 4-butylphenylacetylene were reacted to form 1-(3-fromo4-(4
-ethylbenzoyloxy)phenyl)-2-(4-butylphenyl)acetylene was obtained. It was cyanated according to the method of Example 1, and purified by the usual method to give 6.2 g.
1-(3-dia2-4-(4-ethylbenzoyloxy)phenyl)-2-(4-butylphenyl)acetylene (compound No. 55) was obtained.

The following compounds are produced in the same manner.

(Compound Magnetism 56) 1-(3-cyano-4-(4-propylbenzoyloxy)phenyl)-2-(4-propylphenyl)acetylene, (Compound 57) I-(3-cyano-4-( 4-butylbenzoyloxy)phenyl)
-2-(4-ethylphenyl)acetylene, (Compound 11h59) 1-(2-cyano-4-(4-ethylbenzoyloxy)phenyl)-2-(4-butylphenyl)acetylene, (Compound 11h59) 1- (2-cyano-4-(
4-propylbenzoyloxy)phenyl)-2=(4
-propylphenyl)acetylene, (combined magnetokinetic 60) 1
-(2-cyano-4-(4-butylbenzoyloxy)
phenyl)-2-(4-ethylphenyl)acetylene.

Example 7 29.9 g (0,091 mol) of the corresponding 3-bromo-4-ethoxyiodobenzene according to the method of Example 1
and 14.5 g of 5-butylpyridyl-2-acetylene were reacted to form 1-(3-bromo-4-ethoxyphenyl)-
2-(5-butylpyridyl-2-yl)acetylene was obtained. Furthermore, it was cyanated according to the method of Example 1, and purified by a conventional method to obtain 5.9 g of 1-(3-cyano-4-ethoxyphenyl)-2-(5-butylpyridyl-2-yl)acetylene ( Compound 11h61) was obtained.

The following compounds are produced in the same manner.

(Compound magnetism 62) 1-(3-cyano-4-propoxyphenyl)-2-(5-propylpyridyl-2-yl)
Acetylene, (Compound magnetokine 63) 1-(3-cyano-4-butyloxyphenyl)-2-(5-ethylpyridyl-2-yl)acetylene, (Compound magnetokine 64) 1-(3-cyano-4 -ethylphenyl")-2-(5-butylpyridyl-2yl)acetylene, (Combined Magnetism 65) 1-(3-cyano-4-propylphenyl)-2-(5-propylpyridyl-2-yl)acetylene, (Compound 11h66) 1-(3-cyano-4-butylphenyl)-2-(5-ethylpyridyl-2-yl)acetylene, (Compound Kinetic 67) 1-(2-cyano-4-ethoxyphenyl)- 2-(5-Butylpyridyl-2-yl)acetylene, (Compound 11kL68) 1-(2-cyano-4-
Propoxyphenyl)-2-(5-propylpyridyl-2-yl)acetylene, (Compound Magnetism 69)1-(2-cyano-4-butyloxyphenyl)-2-(5-ethylpyridyl-2-yl) Acetylene, (Compound Magnetism 70) l-(2-cyano-4-ethylphenyl)-2-(5-butylpyridyl-2-yl)acetylene, (Compound Magnetism 71) 1-(2-cyano-4- (compound 11h72) 1-(2-cyano-4-butylphenyl)-2-(5-ethylpyridyl-2-yl)acetylene.

Example 8 29.9 g (0,091 mol) of the corresponding 3-bromo-4-ethoxyiodobenzene according to the method of Example 1
and 14.6 g of 5-butylpyrimidinyl-2-acetylene
to react with 1-(3-bromo-4-ethoxyphenyl)
-2-(5-butylpyrimidinyl-2-yl)acetylene was obtained. It was cyanated according to the method of Example 1, purified by a conventional method, and 5.5 g of 1-(3-cyano-4-
ethoxyphenyl)-2-(5-butylpyrimidinyl-
2-yl)acetylene (compound Na73) was obtained.

The following compounds are produced in the same manner.

(Compound 11h74) 1-(3-cyano-4-propoxyphenyl)-2-(5-propylpyrimidinyl-2-yl)acetylene, (Compound Il!175) 1-(3-cyano-4-
butyloxyphenyl) -2-(5-ethylpyrimidinyl-2-yl)acetylene, (Compound 76) 1-(3-cyano-4-ethylphenyl)-2-(5-7'ylpyrimidinyl-2-yl) ) Acetylene, (Compound Magnetism 77) 1-(3-cyano-4-propylphenyl)-2-, (5-propylpyrimidinyl-2-yl)acetylene, (Compound N1178) 1- (3-cyano-4- butylphenyl)-2-(5-ethylpyrimidinyl-2-yl)acetylene, (Compound Magnetism 79)1-(2-cyano-4-ethoxyphenyl')-2-(5-butylpyrimidinyl-2-yl)
Acetylene, (Compound 14180) 1- (2-cyano-4-propoxyphenyl) -2-(5-propylpyrimidinyl-2-yl)acetylene, (Compound 11h81) 1- (2-cyano-4-butyloxyphenyl) -2-(5-ethylpyrimidinyl-2-yl)acetylene, (compound 11h82) 1-(2-cyano-4-ethylphenyl)-2-(5-butylpyrimidinyl-2-yl)acetylene, (compound magnetokinetic 83) 1-(2-cyano-4-propylphenyl)-2-(5-propylpyrimidinyl-2-yl)acetylene, (Compound N184) 1-(2-cyano-4-butylphenyl)-2-(5 -ethylpyrimidinyl-2-yl)acetylene.

Example 9 The corresponding 3-bromo 4 (
21.8 g (0.05 mol) of 2-(4-ethoxycyclohexyl)ethyl)-1-iodobenzene and 7.9 g of 4-butylphenylacetylene were reacted to form 1-(3-
Bromo-4-(2-(4-ethoxycyclohexyl)ethyl)phenyl)-2-(4butylphenyl)acetylene was obtained. Furthermore, it was cyanated according to the method of Example 1, and purified by the usual method to produce 7.2 g of 1-(3-cyano-
4-(2(4-ethoxycyclohexyl)ethyl)phenyl)-2-(4-7'tylphenyl)acetylene (compound N185) was obtained.

The following compounds are produced in the same manner.

(Compound 11m86) 1- (3-cyano-4-(
2-(4-propoxycyclohexyl)ethyl)phenyl)-2-(4-propylphenyl)acetylene, (Compound Magnetism 87)l-(3-cyano-4-(2-(4-
butyloxycyclohexyl)ethyl)phenyl)-2
-(4-ethylphenyl)acetylene, (compound 11h8B) l -(3-cyano-4-(
2-(4-ethylcyclohexyl)ethyl)phenyl)
-2-(4-7'tylphenyl)acetylene, (Combined Magnetism 89)1-(3-cyano-4-(2-(4-
propylcyclohexyl)ethyl)phenyl)-2-(
4-propylphenyl)acetylene, (compound 11h90) 1-(3-cyano-4-(
2-(4-butylcyclohexyl)ethyl)phenyl)
-2-(4-ethylphenyl)acetylene, (compound 11h91) 1-(2-cyano-4-(
2-(4-ethoxycyclohexyl)ethyl)phenyl)-2-(4-butylphenyl)acetylene, (Compound Magnetism 92)l-(2-cyano-4-(2-(4-
propoxycyclohexyl)ethyl)phenyl)-2-
(4-propylphenyl)acetylene, (compound magnetism 93)1-(2-cyano-4-(2-(4-
butyloxycyclohexyl)ethyl)phenyl)-2
-(4-ethylphenyl)acetylene, (compound magnetism 94)1-(2-cyano-4-(2-(4-
ethylcyclohexyl)ethyl)phenyl)-2-(4
-7'tylphenyl)acetylene, (compound magnetokinetic 95)l-(2-cyano-4-(2-(4-
propylcyclohexyl)ethyl)phenyl)-2-(
4-7”ropylphenyl)acetylene, (compound 11h96) l -(2-cyano-4-(
2-(4-butylcyclohexyl)ethyl)phenyl)
-2-(4-ethylphenyl)acetylene.

Example 10 (composition) The N-1 point of liquid crystal composition A consisting of: 64.0°C and 25°C
The viscosity at is 13.3cP, Δn is 0.085, Δε
was -1,07.

90% by weight of this liquid crystal composition A was added with flame 1-(3-cyano-
4-ethoxyphenyl)-2(4-propylphenyl)
N of the liquid crystal composition containing 10fffffi% of acetylene
-1 point slightly decreased to 56.1℃, viscosity at 20℃ was 19.1cP, Δn increased to 0.099, and Δε was -
The absolute value increased to 1 and 4.

According to this example, the compound of general formula (1) can be used without significantly lowering the N-1 point of the base liquid crystal composition, minimizing the increase in viscosity, and increasing the absolute values of Δn and Δε. It can be understood that it has the effect of increasing the

(Effects of the Invention) According to the present invention, a liquid crystal compound having a large negative dielectric anisotropy value and a large refractive index anisotropy value, and a liquid crystal composition suitable as a component of a liquid crystal display element can be obtained. .

that's all

Claims (3)

[Claims] (1) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼…(I) (In formula (I), R^1 and R^2 each independently represent an alkyl group or an alkoxy group having 1 to 10 carbon atoms, A, Y, and Z each independently represent 1,4-phenylene (one or two CH groups present in this group may be replaced with N, and one or two CH groups present in this group may be replaced with N).
(H may be replaced by F) or trans-
1,4-cyclohexylene, B is -COO-, -
OCO-, -CH_2O-, -O-CH_2- or -
CH_2CH_2-, W is -CH_2CH_2-
and k, l, m, and n are each independently 0 or 1). (2) A liquid crystal composition containing at least one compound of formula (2) according to claim 1. (3) A liquid crystal display element comprising the liquid crystal composition according to claim 2.