JPS60163864A - 2,5-disubstituted pyridine, manufacture, liquid crystal material and electrooptical device - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] The present invention relates to heterocyclic compounds, more particularly λ.

! - Disubstituted pyridines, processes for their production, liquid crystal materials for information display and processing systems (meaomorphlam
material) and electro-optical devices.

! , j-disubstituted pyridines are useful in organic synthesis intermediates, liquid crystals, pharmaceutical compositions, and many other applications.

The most important application of liquid crystals is their use as agents in electro-optical devices for information display and processing. Liquid crystal materials used for this purpose are subject to a whole series of requirements, the most important of which are operating temperature range and dielectric constant. These properties should always be considered first in selecting the liquid crystal material components.

The most well-known liquid crystal electro-optical device is the twist display, which uses a nematic liquid crystal material with positive dielectric anisotropy (Δε<0). This property is achieved by incorporating into the liquid crystal material a nitrile group-containing component with a permanent dipole moment oriented in the direction of the long axis of the molecule.

Examples of such compounds include cyanobiphenyls of formula (1) (UK Patents Nos. 1, 2, 2 & 2 & C1, CIIX, /7 issued in 1999) and compounds of formula (II)
cyanophenylcyclohexane (Soviet Patent No. 7)
J gs / No., Int, C1, CO ri 3/
341. /77g (see publication).

In the formula, R represents cn H2fFF1, and n represents an integer from 3 to g.

Recently known liquid crystal compounds have the general formula (wherein R1 and R2 are CnH2n+1, and n is /~
, g is represented) +,4t-dialkyl-2,3-diphenylpyridine (D, Demus et al., I.F 1
iisa igeKrlstale in Table
lan, /ri74', “ME B Deutache
rVerlag f ”i rGrundstoff
1nduatrie” Publisher, Leipzig, p2!'
(see I).

The use of these compounds for liquid crystal materials with positive dielectric anisotropy is limited by their very high melting points (100° C. to 273° C.) and low dielectric constants.

In fact, many liquid crystalline -,1-disubstituted pyridines containing nitrile groups are also known (■-■).

(In the formula, R = Cn Hzn + 1, n = A ~ri)
(In the formula, R = CnH2n+1, n = 4' ~ J') (
In the formula, R= Cn H2n+1, n-4' ~ f) Formula (
The phase transition temperatures of the compounds IV) to (VI) do not fully satisfy the requirements imposed on the components of the liquid crystal material. Thus, the compound of formula (IV) (n = l-) has a low clearing point (g"c) and a relatively high melting point b (SS"
C) (A, 1. Pavljucbenko, E
, 1. Kovahev.

V. V. Tltov, “Khlm lja get
erocykl 1choaklkhsoedinen
y” (“Chemistry of Heterocyclic Compounds” Russian Magazine) Zinat
ne Publisher, Riga /ri J'/, NO/, pp, I
! - see JfJ). Compounds of formulas (V) and (Vl) also have very high melting points (5g°C to 27°C), and no tautotropic liquid crystals have been found among the compounds of formula (V).
-The clearing point of the degraded compound (W) is within the range of ♂O-''10°C (A.

1, Pavljuchenko, V, V, Tl
tov, N, 1. Sm1rnova.

V. T. Qrachev, “Chemistry of Heterocyclic Compounds” magazine, “Zinatne” Publisher, Riga, / Ri 1
0. Na7. pp, Ir1-r/reference).

The dielectric constants of the compounds of formulas QV) to (VI) are not particularly high.

Although the compound of formula (■) is simply described as liquid-crystalline, its properties or the method for its preparation are not disclosed in the literature (V, T, Gracbev).

B., E., Zaitaev, E., M., Itako.
vlch, A, 1. Pavljuchenko.

V, V, Titov, K, M, DJumaev, r Molecular Crystals and
LIquld Crystala J, /rif/,
vol.

it, Nn //2, pp, /33~/4'
(see J).

Cyanopyphenyl derivative of formula (■) and cyanophenylcyclohexane M of formula (It)! The conductors are those used for nematic liquid crystal materials. For example, 3゛0
molar ratio goupentyl-t'-cyanopiphenyl, Δ molar ratio gouhebutyl-l'-cyanobiphenyl, 76 molar ratio goupentyl-t'-cyanobiphenyl,
A liquid crystal material consisting of l-pentyl+f-cyanoterephenyl and tamor group is known, and has the following properties. Δε=/l/,, liquid crystal temperature range (range
of exit of meao-phas
e) - Tal 16θ℃, threshold voltage of twist effect (Utbr,) = /, jV, saturation voltage (U
sat, )=/, ri+V. This mixture was found to be very useful in the manufacture of display devices and was given the trade name E7 (
(available from BDHCo, UK).

A mixture based on cyanophenylcyclohexane of formula (II) has a small Δε value and therefore a relatively high threshold voltage and control voltage.

It is an object of the present invention to provide J,j-disubstituted pyridines which have positive dielectric anisotropy and are suitable for effective use as components of liquid crystal materials.

Another object of the invention is that λ,! is simple and does not require high material costs and can be easily implemented on a commercial scale. - To provide a method for producing disubstituted pyridine.

Another object of the invention is to have a wide operating temperature range;
If the threshold voltage and control voltage are small positive
An object of the present invention is to provide a liquid crystal material having anisotropy.

Yet another object of the present invention is to provide an electro-optical device for monochrome or color information display that can be used effectively under both static and multiplex control conditions.

These objectives are achieved by the following general formula according to the invention, where R is Cn H21+1, Cn H2n+10, n is ti-r
) is a new 2. This is accomplished by providing a j'-disubstituted pyridine.

These compounds of formula (■) under normal conditions consist of colorless crystals that are stable during storage and under operating conditions in electro-optical devices. The melting and clearing points of these compounds and their dielectric constants make them very favorable for their use as components of liquid crystal materials.

According to the invention, co,j-disubstituted pyridines of formula (■) are prepared by reacting pyrylium salts of formula (■) with ammonium acetate in an organic medium according to the following formula:

In the formula, R is Cn H2n+1 or Cn H2n+t
O, and n represents <z−y.

The pyrylium salt (IX) is prepared from substituted phenylacetic acid and guccianoacetophenone according to the following formula.As can be seen from the above formula, the compound of formula Q'1ll) is based on relatively cheap and readily available raw materials. - The method consists of a few steps that do not require complex processing equipment and can be easily carried out on an industrial scale.

The present invention also provides general formula (Vffl) and general formula (■): where -R= CnH2n+4 s enH21H-10
, n = 41~g, where R= Cn I (2n+1, n-/~ri,
The present invention relates to a liquid crystal material containing at least one type of λ,j'-disubstituted pyridine represented by:

According to the invention, this material can further include organic dielectrics and dichroic dyes can be added for the purpose of color display of information on the housing.

The liquid crystal material has the formula (■) already known in the literature,
J-disubstituted pyridine is present (V, T, Grac
hev.

B, E. Zaltsev, E. M. Itskov
ich, A, 1. Pavljuchen-ko
, V.V., Titov, K.M., Djurnae.
Author: v 1 [Malecular Crystals an
d Liquid CrystalaJ/! #/.

vol, Aj, Nn///2. pp, /33~
/112). However, neither the properties of such compounds nor their preparation methods have been disclosed to date. These compounds can be prepared from the corresponding pyrylium salts according to the following formulas.

C10 key (X) (■) In the formula, R represents Cn　H2n+1, and n represents /.

In both cases, the main steps in the synthesis are from the pyrylium salt to 2. This is a conversion to a j′-disubstituted pyridine derivative.

Bromine derivatives of formula (X) are converted to the desired products of formula (■) in conventional manner, ie by treatment with copper cyanide.

The phase transition temperature and dielectric constant of the compound (■) make it favorable for its use as a component of liquid crystal materials.

The present invention provides a liquid crystal display device that has a broad operating temperature range and a large positive dielectric anisotropy, and is capable of producing an electro-optical device that operates effectively under both static and dynamic control conditions. It enables the production of materials.

The present invention also provides 2. of the general formula (■) and (or) the general formula (■), which is interposed between two non-electrical optically transparent plates each having a transparent electrode inside. The present invention relates to an electro-optical device including a liquid crystal effecting agent (at least one type of j-disubstituted pyridine). A polarizing plate can be provided on the outside of the transparent plate.

This electro-optical device according to the present invention will be explained with reference to the accompanying drawings showing its principle diagram. The device comprises two glass plates or other non-conducting transparent plates positioned opposite each other.
It consists of an effecting body (liquid crystal material layer) interposed between. board-
A transparent electrode 3 is fixed to the inner surface of the transparent electrode 3, and a conductive wire 1 for connecting to a power source (not shown) is provided on the transparent electrode 3.

If liquid crystal materials containing dichroic dyes are used, the device can be used without polarizers or on the outside of one plate 2 -
It is possible to provide and use a number of polarizing plates j. When operated under twist display conditions, the device should be provided with two polarizing plates 3 on the outside of both plates.

Due to the device according to the invention, the liquid crystal material molecules in their initial state (before application of the electric field) are aligned parallel to the transparent plate. As a result, the orientation direction on one plate of the twist display device forms an angle of γd with respect to the orientation direction on the other plate.

When an electric field is applied, the liquid crystal molecules are reoriented so that their long axes are perpendicular to the plates. This is visually manifested as a color change of the cell (when using liquid crystal materials containing dichroic dyes) or blackening (under twisted conditions).

The invention will be further explained in the following sections/~3, where Examples/~3 show the method for preparing the compound of formula (■) and its properties, and Examples 10~/6 illustrate the preparation of the compound of formula (■). Example 7 to IA3 shows the manufacturing method of liquid crystal material for twist display device and its properties (Example 77 to IA3).
o) and a method for manufacturing a liquid crystal material containing a dichroic dye and its properties (Example≠/~Hiroshi 3).

Example 1 This example and Examples 2 below illustrate the preparation of a compound of formula (■).

03 moles of anhydrous dimethylformamide, 0 phosphorus oxychloride
．． 3 mol are added dropwise at 0'C, then o, i mol of goobutylphenyl acetic acid are added in portions at a temperature of -10°C.

The mixture was incubated at 20 °C for 7 h, at AO °C for 2 h and at go °C.
Stir for 5 hours. The dimethylbormamide is distilled off in vacuo, the residue is cooled, and the residue is mixed at a temperature of -10 DEG C. with 0.7 mol of water), O ml of water in the form of a saturated aqueous solution and 0.7 mol of magnesium perchlorate. The precipitated salt is separated off and washed with ether to give the salt 2i,zi with a melting point of 102°C.

Salt produced in this way! i anhydrous pyridine 10
ml solution +-cyanoacetophenone 0.0/
Add 2 moles of Ir, then 2 moles of sodium methylate
．． Add the jM bath solution slowly dropwise at a temperature of 20°C.

Stirring was continued for 2 liters at 20°C for 1 hour, and pyridine was distilled off.
The residue is treated with water and extracted with benzene. Benzene was distilled off and the residue was recrystallized from methanol.
Dissolve in 0-. The obtained solution was added to 2N hydrochloric acid,
Stir for 30 minutes, filter the residue and wash with methanol.
After dissolving in 10ml of acetic acid, 70ml of perchloric acid
Add slowly dropwise.

After diluting the mixture with diethyl ether and filtering off the residue,
Dissolve in a mixture of 30 rttl acetic acid and rg ammonium acetate. The mixture was stirred for 2 hours, poured into water after cooling, and the residue was filtered off and recrystallized from methanol.
r-(ll-butylphenyl)-2-(4'-cyanophenyl)-pyridine having a melting point of 5°C and a clearing point of 233°C is obtained. Dielectric constant (measured at yj”c): εH”23. t,
ε1=t, 3, Δg=10/7.3 Table/ shows examples λ~ showing the properties of compounds corresponding to formula (■) and obtained by the same method as described in Example 1 above. List the following.

Table/ r-(+-alkyl or alkoxyphenyl) of the following formula
-,! Properties of -(Il-cyanophenyl)-pyridine
Example 1O This example describes the preparation of a compound of formula (■).

! -Production of phthyl, 2-(ll-cyanophenyl)-pyridine N-(hexenyl-/)-piperidine 10,29 and triethylamine♂, JlI- diethyl ether solution 10
20 g of a diethyl ether solution of p-7''comophenyl-β-chlorovinylketone/4',7II was added dropwise with stirring and left at room temperature for 72 hours.The reaction mixture was diluted with water and the ether was distilled off. The residue is filtered off and, after washing once with water, is mixed with a solution of 54% perchloric acid ΔG in water. The mixture is heated under reflux for 5 minutes. The precipitate that forms After cooling, the material was filtered, washed with ether and diluted with vinegar (fHjoml and ammonium acetate ao).
Mix with the solution of g. The mixture was refluxed for 1 hour and 30% water
Pour into 0 ml and extract with benzene.

The benzene extract is washed with water, dried over sodium sulfate, and then the benzene is distilled off. The residue was recrystallized from benzene to give 1-butyl-λ-(ll-7
"Romophenyl)-hyridine".

! A mixture of -phthyl,2-(4Z-bromophenyl)-pyridine zg, copper cyanide Ar,j(l) and N-methylpyrrolidonyl Oml was refluxed for 2 hours, cooled and J
Pour the extract into a mixture of Bml of ammonia water and 10oml of water, wash the extract with water, neutralize it, and add sulfuric acid) After drying with IJum, pass through an alumina bed with an activity of ■, and elute with benzene. Do it with The benzene was distilled off and the residue was recrystallized from hexane to obtain j-butyl-,2-(lI-cyanophenyl)-pyridine having a melting point of 3/''C and a clearing point of 27.!C.

ε) 1-2, εl == lI3, Δε = +73
Other compounds of general formula (■) are obtained in the same manner as in Example 30.

Their properties are shown in the table below.

Complete table (■)! -alkyl-λ- (tercyanophenyl)
Properties of pyridine 1/, 2 AX, 0 3. ! r, jt 37 /4'
10, 2J/, 2 3 11J3 '13, 7 31r
Ta1. t +, u, j/3, t 3.2. Ko lI
3. J, 2ta / / 10 / J' / Hiro Otsu Kootsu 23
λ,t,2j,! /, 2 +/I, j/, 5 7
．． 2g, j 4'7,! 4' Ta, j +/j,! /
6 139. j lI3 − − +Example 17 Production of liquid crystal material j-Petyl-(lI-cyanophenyl)pyridine 3
ri, θ molar ratio, j-hexyl-,! -(4t-cyanophenyl)-pyridine 1Io3molti and 1-(+-amylphenyl)-,2-(4t-cyanophenyl)pyridine 20. Charge the molar mass into a glass beaker, heat it to 70°C while stirring, and then cool it in a room temperature cabinet. In this way, it has the following properties and ready-to-use viscosity = ,2
7 cPa (2j'C).

Example 1zP-λg In the same manner as described in Example 7 above, the formula (Vlr)
Other liquid crystal materials can be obtained by mixing the compound of formula (■). The resulting liquid crystal material has the composition and properties shown in Table 3 below.

Table 3 Liquid crystal materials containing compounds of the following formula (■) (■) / 2 3 g/g VI I I C3Hu 22JVII C5H
33.0 VII CuHg IAIA, 2 /9 VIII c5H1t, 2j,, tVI I
C2H5co1,0 VI I CuHg / j, r VI I C6H133,2,7 20VI I I C6H1327,2VTI Cll
Hg II/, 7 VII C6I (13J/, / -2/ VIII C11H9/, 5', 2VII
CuHg 3Y, 2 VII C3H1t J', RIVI I (4H17/ 3.7 -Z-I VI I I C7H15/ AJVII
CIIB9 3θ, Hiro VI I C3H1l, 2/j VI I C6H133t, 3 force VI I I C3HH/4t, J VII C3H7/9.2 VI I CuHg 241.7 VI I C3HH/ A, ? VIIC6H13, 2 evening, 0, ), Q VI I I C [1H170/ 1.3V
II cH3,2J-,7 VIT C3H11,2g vIIc7) (1520J VI I C9I(19/ 0.1 (-tJ] -)-!; /, 2 VII C exit 13 30, 7 VII C7H15/7j VI I C3H1? ?, 0 Yu6 VIII C3HH/jj VII C2H5/3.J VII C3H11/Ri・4 VII C6H13X1./ VII C7H45/J −、 7 VI I C8H177, rij7 VIII C7H15/, O VI I C2H5/ 0.O VI I C'3) (7/ A, A VI I CuHg, 2/, / VII C3HH/u, j VI I c6H13,2 /, J VII C7H4510J VI I Cglh7 !, / (,V) VI I C2H5/ l,,j VI I C3H727,,j VII C3H11 7 VII C7H15,2/,j VI I C[1H17/ /, / Table 3 (continued) Example number Properties of liquid crystal material/jl, 7 lrri/zaichi ≠ +79 0.ta /,! +, 20.O9 1/J -4-A1 /, Ot, g +19..2 :L
o-! + Zahiro /, / /, j +/r, t Yuno-7+7QA I, /j /, t +/r, 0.2ko1/3 +t7 /, 2 /j + /1.0yu3 -21 +A3 /, / /-j +/r, 21 1/ko +7g /, /o /, 1. ! 10/za, OJ -74+74A /,, 2 /, lzzj +/f0(2
7) Colo 1 Δ +A2/, 3 /, 7 +/Otsukoko7 1/A +Gθ /, Or /, j +/ri, 0ko8 -lko +'A3 /, OA-/, Guj 10 liters (2g
) Examples q-35 These examples illustrate the production and properties of liquid crystal materials containing organic dielectrics.

In the same manner as described in Example 1, organic derivatives (1) of cyanobiphae = A were added to compounds (■) and (■).
By mixing the = derivative and the cyanophenylcyclohexane derivative of formula (II), other liquid crystal materials having the composition and properties shown in Table 1 are prepared.

Table: Liquid crystal material example number containing a compound of the following formula Composition of liquid crystal material Compound R weight % / , 2 3 ≠ 29 II C3H73A, I I I C3H1130, II c7) (15,2/, / VIII C3HH/2 I , 7 VIII C7H151. I C3HH10+0 VIII CuHg0 /7,9 VI I CuHg 2, 3 VII C3Hu /7.j VII C6H132, 3 3 da II C3H731,3 I I C3HH20,j VIII C7H15/2.t VII C3H1, /4Z, # V engineering I C6H13ko1.7 (3 units) 35 I C3B70 //J I CuHg0 7, O I C3H11010,3 I C6H1:50 7.J I C7) 1150 2.4! I C3H470/ 3.A I C , HI3 J-, 1r VIII C3HHz, t VI I C3HH/ 9.A Table (continued) Example number Characteristic temperature of liquid crystal material [''C] Voltage [v] / j A 7 F +1.9 1 &+7' A /, & 2,3!r 0 -3 + O1, G /J 3/ 1/K 7za 1.6 +2.2 3t -22+6 Otsu /, ≠ 7.ri S -7+70 /,, 2 / +7 (3S) Example 3A In a similar manner as described in the previous example/g, μm butylbenzoic acid chloride-cyanophenyl ester,
Hexylbenzoic acid guccianophenyl ester 21. A
Weight, μm to butyl benzoic acid cucyanophenyl ester #, t'M amount %,! -Methyl-, 2-(cucyanophenyl)kylidine s, oxx-, terethyl-, 2-
(+-cyanophenyl)hyridine 71.2% by weight, '-
Propylleuco(coucyanophenyl)-pyridine 39
0 weight S, '-heptyl-λ-(lIL-cyanophenyl)-pyridine 73.6 weight, j-octyl-1-(
gucyanophenyl)-pyridine, j-nonyl-λ-(
Cucyanophenyl)-pyridine 3. r weight clerk and j
A liquid crystal material consisting of 390% by weight of -(couhexylphenyl)-j-(hiro-cyanophenyl)-pyridine is obtained. m, p, = -/: 1℃, clear point = +72℃,
Uthr, == 1. OV, Usat, = /
,jV.

Example 37 Follow the steps in Example/g! -Propyl-λ-(g(3A
) monocyanophenyl)-pyridine J''wt%, '-amyl-2-(lI-cyanophenyl)-pyridine 390
Weight%, "-trans-butylcyclohexanecarboxylic acid couethyloxyphenyl ester/lr, Oi amount%
, It-trans-hexylcyclohexanecarboxylic acid≠-ethyloxyphenyl ester fluoroM (t'
I) A liquid crystal material consisting of ≠-(Hiroshi-trans-butylcyclohexanecarbonyloxy)-cuscyanodiphenyl//, 0 weight ratio is obtained. The resulting material has the following properties: m, p, = -g6℃, clear point = +6g"c
, U thr, = 1.31 A V , U sat
, = /J/V.

Example 3g In a similar manner to Example/Process, a liquid crystal material is produced which is particularly suitable for use under multiplex control conditions.

The materials are trans-≠-n-butylcyclohexanecarboxylic acid 3o, O weight factor, trans-4t-n-hexylcyclohexanecarboxylic acid 3theta weight factor, cochlorop-(4I--n-hebutylbenzoyloxy)benzoic acid. Gucyanophenyl ester 10]i amount 9L-t
-Propyl-(gucyanophenyl)-pyri 2fufu 0 weight ratio and! - Hexyluko (Hiro-cyanophenyl) - Pyrile 10 weight ratio υ. The material produced in this way has m, p.

Nita ℃, clear point = +grc, U thr, = /,
A V , multiplex ratio /:6.

Example 39 In a similar manner to Example/Process, a liquid crystal material is obtained which is particularly suitable for use under multiplex control conditions.

The materials are: 290% by weight of trans-Hiroshi-butylcyclohexanecarboxylic acid, 2. f, 0 times 1, it'-octyl-
≠-cyanopyphenyl/Ja weight%, J--ethyl-2
-(gucyanophenyl)-pyrylev2. Fuju I1 Section,
! -propyl=2-(gucyanophenyl)-hyricin/i0 i% by weight, s-hexyl-λ-(gucyanophenyl)-pyrylev 2.5% by weight. The material produced in this manner has a melting point of -s'C and a clearing point of +70℃.
, U thr, = /,7 V, and multiplex ratio /:j.

Example G In a similar manner to that described in Example/g above, j-butyl-(gucyanophenyl)-pyridine 24A, 7 parts by weight, j-amyl-1-(gucyanophenyl)-pyridine/'l/ Weight 1, '-hexyluko-(gucyanophenyl)-pyrisif 2114 Weight ratio, j-(≠-butylphenyl)-2-(Hiro-cyanophenyl)-pyridine t
A liquid-crystal material is obtained consisting of 10 parts by weight of guamyl rug'-cyanobiphenyl and 2.2 parts by weight of a red dichroic dye with a positive dichroic ratio io. The material produced in this way has m, p, = -/7℃,
Clear point=+72. ．． lt'C:, Uthr.

= /, / V, Usat, = /, J' V
fal. i: On a sailboat, a twist display can form a colorless symbol on a red background.

Example 1 As described in Example/Za, Obutyluko (gucyanophenyl)-Pyrilef 290 weight ratio,! -amyl~λ-(4t-cyanophenyl)-pyridiyzZ3ml
, s-hexyl-λ-(gucyanophenyl)-pyridine, 29.7 weight factor 1. ．． t-(<z-butylphenyl)-,! -(4=-cyanophenyl)-pyri 2fufufu,
weight, guamyl-7'-cyanobiphenyl 10.
A liquid crystal material consisting of 2 weights φ and a golden yellow dye /, ON amount ratio is obtained. The obtained material is m,p,-/za°c,4
Bright point 72℃, Uthr, =Otsu/VXUaat, =/
, , 5'V can form black symbols on a golden background with a twist display.

Example/In a similar manner as described in Section 1, trans-+-furopyru(<2-cyanophenyl)-cyclohexane 2
t, ♂Mi%,) lance-guamyl-(l-cyanophenyl)cyclohexa 2110 weight to j-armylu,
2-(&-cyanophenyl)-pyri2ph 1.2. weight ratio, j-hexyl-(l-cyanophenyl)-pyridine/9. /weight, s-(lI-hephthylphenyl)
-,2-(9-cyanophenyl)-pyridine ii, l1
Red dye with weight i% and negative dichroism/2. A liquid crystal material having a weight ratio of 0 is obtained.

The material thus produced is rn,p,-/g'C
S? A bright point +63℃, Uthr, =/, jvUaat
,=,2. With OV, a pink symbol can be formed on a solid background.

Example≠3 Trans-gupropyl-(ll-cyanophenyl)-cyclohexane 3
0.0MftN6, 'l-amyl(+-cyanophenyl)-cyclohexane, %X to 201.2! -amylu, 2-(+-cyanophenyl)-pyridine/4',
, 2II weight%, 3-hexyl-,2-(<2-cyanophenyl)-pyridine, 2/, 4 by weight, j-(
*-octylphenyl)-, 2-(+-cyanophenyl)-bili2fufu23fu, and has positive dichroism in the absorption band of l130nm-,! A dye with negative dichroism in the absorption band of lIOnm/,! A liquid crystal material consisting of a weight factor is obtained.

The material produced in this way has m, p, -yuO ℃, clearing point + &&, j'c, U thr, = /, 'l
V, Uaat, = /, riV, and a violet-colored symbol can be formed on a yellow background.

[Brief explanation of the drawing]

The drawing is a sectional view for explaining the principle of an electro-optical device. Applicant's agent: Kiyokin Inomata ■Applicant: Alexander, Wasi Soviet Union. Lievitsch, Ivas Rast, Ulychenko-Be, 57 ■Applicant Vadim, Mikhailou Soviet Union Vytsch, Shoshint, Ulitsch ■Applicant Polis, Georgiou Soviet Union Moynch, Gripov 8, Kabe, -〇Applicant Vladimir, Ivanov Soviet Union Moytschi, Grigos-, 36 ■Applicants Galina, Ivanovna, Soviet Union Khkarpushkinat, Ulitsut□ ■Applicants Yuri, Piotro Soviet Union Huytschi, Bobylevt, Prosbak0 Applicant Alexander, Iva Soviet Union Tonowich, Vasily Oblast , Fukabe,
32 ■Applicant Vladimir, Alekse Soviet Union Moevitsch, Kozno-, Af ■Applicant Valentin, Alek Soviet Union Doseyutchy, Tsverast, Likhatilgoprudny, Moskovskaya, Oblast, Verbomayskaya, 44
-A, Kaliazino, Moskovskaya, Oplus r1
Porewaya, 7, Kabe, 69 Skwa, 10346 & Berezovaya, Aleya, 0 Skwa, 10357\Kolpus 91 East Kabeliazino, Moskovskaya, Oplus γ, Borewaya, 10, Kabe, 36 Riadino, Moskovskoy, Oblast, Mila, 10
, Kabe, 6 Khulekoprgoprudny, Moskovskaya, Ulitsya, Teatralnaya, 12A, Skwa, 103460
, Korgys 20 ＼ Kabelkoprudny, Moskovskaya, Obraskoye, Shotsse, 20, Furbus, ＠ Applicant Gennady, Alek Soseyevich,
Bere 1, Snev ■Applicants Mikhail, Ivanoui Sotschi, Balnikra-Et Federation Moscow, Ulitsa, Cominterna,
3 Corpus, 1, Carvey, 6

Claims (1)

[Claims] General formula 15 (R in the formula is Cn H2n+1 and i'j: Cn
H2n+10, n represents tg) J,j-disubstituted pyridine. 2. General formula (R in the formula is CnH2n+1 or CnH2n+1
0 and n represents 9 to g) is reacted with ammonium acetate in an organic medium in a general formula (where R is Cn H2n+1 or Cn H2n+1
0, n is 4 (-, represents r) 2,! - A method for producing a disubstituted pyridine. 3. General formula (R in the formula is CnH21+1 or CnH2n+t
(represents O, nt/i - r) and (Kakitake) Co,j-disubstituted pyridine represented by the general formula (R' in the formula is Cn 1 (2n+1, n is l-7)) 1. The liquid crystal material according to claim 3, in which the organic dielectric material is present in a casing of 50% by weight. The liquid crystal material according to claim 3 or 7, which includes the liquid crystal material according to claim 3 or claim 7.
~． A liquid crystal effecting body (1) made of a liquid crystal material according to any one of item 5'-7, and a transparent electrode (3) located inside a transparent plate (2) and having a conductor for power connection. An electro-optical device characterized by: