JPS5922964A - Azo-based polychroic dyestuff and liquid crystal composition containing the same - Google Patents

Abstract

NEW MATERIAL:An azo-based polychroic dyestuff of formula I [A<1> is a group of formula II (U<1> and U<2> are each H, halogen, CH3, etc.) or III; X<1> is H, (alkoxy)alkyl, aryloxy alkyl, alkoxy, aryl, halogen, etc.; Z<1>-Z<3> are each H, halogen, alkyl, alkoxy, etc.; Y is O or -NR<1>- (R<1> is H, alkyl, etc.)]. EXAMPLE:A compound of formula IV. USE:Polychroic dyestuffs with high order parameter, usable as a component of liquid crystal composition. PROCESS:For example, an amino compound of formula D<1>-NH2 (C<1> is an aromatic group with no ionic group) is subjected to diazo coupling with a compound of formula V to prepare the objective dyestuff.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an azo pleochroic dye and a liquid crystal composition containing the azo pleochroic dye.

A pleochroic dye is a dye whose absorption intensity of light differs depending on the direction of the dye molecule.In other words, this dye exhibits the property that the absorption transition moment is at its maximum when the direction of the absorption transition moment is parallel to the electric vector of the light. The absorption strength is similar to that of a dog.1. The absorption intensity is the smallest when it is vertical.

In the liquid crystal display element described above, the orientation of the dye molecules can be changed by utilizing the fact that the alignment direction of the liquid crystal molecules changes when an electric field is applied. This allows the color of the liquid crystal display element to be changed by applying a voltage. Considering the liquid crystal compound as the host and the dye as the guest, this color change is called the guest-host effect.

Among pleochroic dyes, especially those with parallel dichroism, the direction of the visible light absorption transition moment is almost parallel to the long axis direction of the molecule, and it dissolves as a guest molecule in the host liquid crystal. When this happens, the dye molecule long axes have the property of being aligned in the same direction as the alignment direction of the liquid crystal molecule axes.

For example, in a liquid crystal display element subjected to a homogeneous alignment treatment in which the liquid crystal composition consists of a pleochroic dye with parallel dichroism and a nematic liquid crystal compound with positive anisotropy, the long axis of the dye molecule is Similarly, a homogeneous orientation is formed parallel to the electrode surface and aligned in a constant direction. When white light propagates in a direction perpendicular to the electrode plane and polarized in the same direction as the alignment direction of the liquid crystal molecules through the liquid crystal layer in such an aligned state, its electric vector becomes parallel to the dye molecules. , a specific wavelength range is particularly strongly absorbed, and as a result, the liquid crystal layer becomes strongly colored. Next, when a full electric field is applied to the liquid crystal layer, the long axes of the dye molecules form a homeotropic alignment because the diTL anisotropy of the host liquid crystal is positive.

Then, the long axis of the dye molecule is perpendicular to the electric vector of the incident white light, so that the incident light is hardly absorbed by the dye molecule, resulting in the liquid crystal layer being in a weakly colored state.

The guest-host effect is not limited to those using the above-mentioned nematic liquid crystal compounds, but can also be dramatically obtained using, for example, those using smectic liquid crystal compounds or those making full use of the cholesteric-nematic phase transition. In the case of utilizing the phase transition, each molecule of the cholesteric liquid crystal assumes a helical molecular arrangement in an element subjected to homogeneous alignment treatment. When white light propagates perpendicular to the gold electrode in the liquid crystal layer, the dye molecules are oriented in various directions, so that specific wavelength regions of all polarized light components are particularly strongly absorbed by the dye molecules. As a result, the liquid crystal layer becomes strongly colored. Next, the liquid crystal layer IC [when positive gold is applied, cholesteric liquid crystal nN
When the anisotropy is positive, the helical molecular arrangement is dissolved and the long axes of the dye molecules form a homeotropic alignment similar to that of liquid crystal molecules. As a result, the liquid crystal layer becomes weakly colored.

The above pleochroic dyes have (1) high order parameters (represented by the symbol S)% in the host liquid crystal (2) sufficient solubility in the host liquid crystal (131) high stability against heat and electricity. , and (4) an arbitrary hue depending on the purpose is required. In particular, in order to enhance the contrast of the element, at least (1) and (2) above are required.

The order parameter S is calculated using equation (1), and is experimentally determined using equation (It). In the formula %COθ! The term 0 is the time-averaged angle between the absorption axis of the dye molecule and the alignment direction of the liquid crystal molecules, and A7/A is the angle between the absorption axis of the dye molecule and the alignment direction of the liquid crystal molecules, and A7/A are the angles that are parallel and perpendicular to the alignment direction of the liquid crystal molecule, respectively. It is determined by the absorbance of dye molecules against polarized light.

B == (j cos'θ−/ )/, 2
・・・・・・(1) S=(A/−A soil)/(−2A↓10A/) ・・・・・・(It) For parallel dichroic pleochroic pigments, the S value is The closer you get to the theoretical maximum value, the more
The degree of residual color in a weakly colored state is reduced, and EA enables clear display with high contrast.

An object of the present invention is to provide a liquid crystal composition and a display body capable of displaying novel parallel dichroic pleochroic dyes with large contrast and clear display that satisfies the above-mentioned requirements +1), +21, and (3). be.

The relationship between the molecular structure and color properties of pleochroic dyes has not yet been fully clarified, and the above-mentioned performance requirements for the desired hue cannot be achieved. It is a difficult task to select all the pleochroic dyes that satisfy all of them, and it is not easy to select them by analogy from known materials.

As a result of extensive studies, the present inventors have determined that order parameters and solubility, especially pleochroic dyes, can be improved by introducing a benzene ring or a cyclohexane ring into an azo dye matrix through a -NH-OH,- bond. The present invention was completed with the conclusion that the characterizing order parameters would be significantly improved.

That is, known literature in which the influence of % substituents on order parameters is discussed, such as A, J31oom
and Pl, L, ni, Humg, MO'l, 0r
y8t,'L1g.

Crypt, , /ri77 VolgOp27.3-
．． 2.2/ and Hidehiro Seki, Tatsuo Uchida, et al.'s research report gD-77-/jp/-7 of the Institute of Electronics and Communication Engineers, generally the following basic skeleton (in the formula, ge is an aromatic group) is used. In the azo dye that has
As the substituent Ra, H4 increases in the order of methyl group, ethyl group, propyl group, butyl group, etc.,
It is known that when the order parameter decreases.

However, as is clear from the following comparative example, the fact that the dye of the present invention containing a monosubstituent with a large number of carbon atoms exhibits a high-order Φ parameter is something that could not be expected from the prior art.

Comparative Example 1 0, N QN=NONHOH, -C>oC,H, (n
) (dye of the present invention) 0. / 7 Comparative example 4 ρ, female 7 IJ (I3-00.H, (n) θ, 7
4t (dye of the present invention) Comparative example 3 (conventional dye) (dye of the present invention) 0.77 Comparative example order parameter 0.72 (n) Mackerel 0-C) -011,11N-C>kN-CJ
N=N (yN=YNHOH,000,H,,(n)
0, r
It is known that when the number of carbon atoms in 4 is small, such as in a methyl group, the solubility decreases. Therefore, it is possible to optimize the solubility for liquid crystal mixtures without incurring a decrease in order parameters.

That is, the gist of the present invention is as follows.

General formula [■] , zf' represents a hydrogen atom, a hydrogen atom, an alkyl group, an alkoxy group, an acylamino group, a cyanide group, and 2' and
Additionally, ka and z' may be linked to each other to form an aromatic ring. Y represents an oxygen atom or a 1-N- group, R1 represents a hydrogen atom or an alkyl group, and R1n may be connected to z4 to Z6 to form a star. Azo-based multicolors represented by (A to G represent a hydrogen atom, a hydrogen atom, a methyl group, a methoxy group, an ethoxy group, and D' and D'' represent an aromatic group that does not have an ionic foundation.) liquid crystal compositions containing color pigments and pigments.

The present invention will be fully explained below.

Specific examples of aromatic groups not containing an ionic group of D' to DI in the general formula [IJ include penzene-based, naphthalene-based, or heterocyclic aromatic groups; These aromatic groups may be substituted with nonionic groups, and are preferred nonionic groups. Examples of the functional group include an alkoxy group, a cycloalkyl group, an alkyl group or a cycloalkyl group that may be substituted with an aryl group; an alkyl group, an alkoxy group, a cycloalkyl group, an aryl group, a cyano group,
A carboxylic acid ester group, an aryl group which may be substituted with a halogen atom or an acyloxy group; an arylazo group;
Heterocyclic azo group; Halogen atom; Carboxylic acid ester group Niacyloxy group; Trifluoromethyl group; Nitro group;
Alkylsulfonyl group; sulfonic acid ester group; amino group; acylamino group; cyclic amide group such as pyrrolidino group, mornolino group, piperidino group, piperazino group; may be substituted with alkoxy group, aryl group ° or cycloalkyl group Alkylamino group or dialkylamino group; examples include heterocyclic groups such as pyridine ring, pyrimidine ring, thiazole ring, oxazole ring, oxadiazole ring, thiadiazole ring, thiophene ring, furan ring, and dioxane ring.

Specific examples of 2-2 include hydrogen atoms, alkyl groups such as methyl groups and ethyl groups, alkoxy groups such as methoxy groups and ethoxy groups, acylamino groups such as acetylamino groups, and halogen atoms such as fluorine atoms, chlorine atoms, and bromine atoms. Examples include atoms and cyano groups.

Specific examples of 1S and x2 include a hydrogen atom, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, a linear or branched chain having a number of carbon atoms of / to /I, an alkyl group, or an alkoxy group: carbon Number of atoms: /~/-20 Straight chain or branched chain alkyl group, or cycloalkyl group or aryl group that may be substituted with an alkoxy group: an alkoxyalkyl group, an alkoxyalkoxy group, having 20 or less carbon atoms, or Dialkylaminoalkyl group; includes an aryloxyalkyl group or an arylaminoalkyl group which may be substituted with a nonionic substituent such as an alkyl group, an alkoxy group, a cycloalkyl group, an aryl group, an aromatic azo group, and further Examples of xl include e and a group represented by the following general formula [...], and f includes an alkylaminoalkyl group having 20 or less carbon atoms. Among these, xl includes an azo dye group represented by the following general formula Ell] (in the formula, Y is an oxygen atom, -N- group, uj is a hydrogen atom,
An alkyl group preferably represents an alkyl group with up to 1 carbon atoms/-. ) is one of the preferred ones. i.e. 1
In the present invention, in the case where the azo dye skeleton has an -NHO-bond at the end, the azo dye skeleton may have a plurality of C7) NI(OHt- bonds in the middle and/or at the end).

In addition to the disazo e skeleton, polyazo skeletons such as trisazo, tetrakisazo, and pentakisazo may also be mentioned, and these dye skeletons may have a heterocycle containing a nitrogen atom, an ionic atom, or an oxygen atom. These azo dye skeletons may contain nonionic substituents, and among the nonionic substituents.

It is preferable that the sum of the carbon numbers of the alkyl chains contained in both the substituents located at both ends in the long axis direction of the dye molecule is 3 or more.

The dye of the present invention has, for example, the same meaning as in the following general formula % (wherein d represents the general formula III). ), known diazotization and coupling methods, the following general formula (wherein 21-I, AI, and X'' have the same meanings as in the front nail general formula [1]) It can be produced by reacting with a compound represented by ) using a conventional method.

In addition, as another manufacturing method, the following general formula (in the formula, D''
zl~11 has the same meaning as in front claw general formula C1)
ft, all have. ) is represented by the following general formula % (in the formula, 5xVi halogen atom, sulfonyloxy group, %AI, and X' have the same meanings as in the front nail general formula [I]). Is there a known method of reacting with a nitro compound, or two molecules of a nitro compound? Known methods for synthesizing an azo compound by reduction can also be applied.

The nematic liquid crystal used in the present invention can be selected from a wide range as long as it exhibits a nematic state in the operating temperature range.

Further, by adding an optically active substance to such a nematic liquid crystal, it is possible to make it take a cholesteric fMk. Examples of nematic liquid crystals include the substances shown in Table 1 or derivatives thereof.

Table 1 In the above table, R' is an alkyl group or an alkoxy group,
represents a nitro group, a cyano group, or a halogen atom.

All of the liquid crystals in Table 1 have positive dielectric anisotropy, but the known ester-based, azoxy-based, azo-based liquid crystals, which have negative dielectric anisotropy,
A silane-based, pyrimidine-based, diester-based, or vinyl ester-based liquid crystal can also be mixed with a liquid crystal having positive dielectric anisotropy to form a positive liquid crystal as a whole.

'Also. ujM,! Of course, even a liquid crystal with negative fi4 orientation can be used as is if an appropriate element configuration and driving method are used.

The host liquid crystal substance used in the present invention may be any of the liquid crystal compounds shown in Table 1 or a mixture thereof, but the following four
tN class liquid crystal compound ○s'kh k-g 3. r
, y7gIBe4 from Merck & Co. as a mixture of ZLnie//! 1.2 and the following seven types of liquid crystal compounds ,2
”IN amount 9bOxH+tOM ON/&! A liquid crystal material sold under the trade name E-7 by the company Brlt, ieh Drug House as a mixture of %C, H++WcN']it% has been found to be particularly useful in the present invention.

As the optically active substance added to the liquid crystal composition of the present invention, chiral nematic compounds such as 1,2-methylbutyl group, 3-methylbutoxy group, 3-methylpentyl group, 3-
There are compounds introduced into optically active nematic liquid crystal compounds such as methylpentoxy group, goomethylhexyl group, and goomethylhexyl group. Tokukai Akira again! r/-4t!
Alcohol fat conductors such as t-menthol and d-borneol shown in Publication No. 86, d-camphor, ketone derivatives such as 3-methylcyclohexane, d-citronella relatives, t-
Of course, optically active substances such as carboxylic acid fatty conductors such as phosphoric acid, aldehyde derivatives such as d-linoneral, alkene derivatives such as d-linonene, and other amine, amide, and nitrile derivatives can be used.

As the device used in the present invention, any known liquid or crystal display device can be used. That is, in general, transparent electrodes in an arbitrary pattern are provided on two glass substrates, at least one of which is transparent, and a VC element is placed so that the two glass substrates are parallel to each other with an appropriate spacer interposed so that the electrode surfaces face each other. The complete configuration is used. In this case, the gap between the p elements is determined by the spacer. The element gap is 3~
700 μm, especially j, jrO μm is preferable from a practical standpoint.

Examples of parallel dichroic pleochroic dyes used in the liquid crystal composition of the present invention and liquid crystal compositions using these dyes will be specifically described below using Examples.

Examples Examples of the pleochroic dyes of the present invention are shown in Table 1 along with the order e-grammeter (S) and hue.

The characteristics of each dye listed in Table 2 were investigated as follows. That is, one of the dyes shown in Table 1 is added as a pleochroic dye to the above-mentioned phenylcyclohexane-based mixed liquid crystal ZL//J, 2, and heated to 70'Q or higher to make the liquid crystal isotropic. The process of stirring the liquid well and leaving it to cool was repeated to dissolve the dye.

The above-mentioned liquid crystal composition made of PA in this way has a transparent electrode, and the surface in contact with the liquid crystal is coated with polyamide resin gold and cured, then rubbed and subjected to a homogeneous alignment treatment. It was sealed in an element with a diameter of 70~/θθμm. When no voltage is applied in the element subjected to the alignment treatment, the liquid crystal composition is in a homogeneous alignment state as shown in FIG. 1, and the dye molecules are also aligned in the same manner according to the host liquid crystal.

The structure of the liquid crystal display element shown in FIG. 1 is a general one except that the liquid crystal composition of this example is sealed.

That is, the element has upper and lower transparent glass substrates.

Transparent electrodes formed inside each substrate, liquid crystal molecules 3 sandwiched between each substrate, and polychromatic light are polarized in direction 2 and reach the element as incident white polarized light ♂. . still,
ri is an observer.

The absorption spectrum of the liquid crystal composition of this example was measured using light polarized parallel to the orientation direction of the liquid crystal molecules and fc light polarized perpendicular to the image. Find the maximum absorption wavelength on A/// and A1ζ. In determining the absorbance of the dye, corrections were made for absorption by the host liquid crystal and glass substrate and reflection loss V of the element. Using the absorbance value A/ of the dye for each of the above-mentioned polarized lights and the value on A obtained in this way,
The S value was calculated from the above formula (II).

Example 2 Ethyl P-aminobenzoate/! -t, V, who Hydrochloric acid 3-1 water 20 ml ICO~j 'O with sodium nitrite 0.7! After stirring for 3 hours at the same temperature, sulfamic acid was added to eliminate all excess sodium nitrite, and a diazo solution was prepared by FA.

Add diazo liquid gold to a mixture of the following compound 2.9tf synthesized by a known method and tetrahydrofuran θrnl, and at 70°C or below! Let it react for a while, add 〃ml of water and precipitate? After removing F, it was purified by Kazimkuroit method to obtain pigment gold in the λth surface layer. The melting point of this dye is 73.2~/! 9. ! 'O aashi.

The aforementioned phenylschiff tetrahexane mixed liquid crystal ZL knee//
The maximum absorption wavelength in J and Z was G J Onm. Example 3 The following compounds were all reacted with P-nitroaniline in the same manner as in Example A to synthesize the dyes shown in Table 2 Ar. The melting point of this dye is /, 26”, j ~ /, 22
The maximum absorption wavelength was 4t70 nm.

EXAMPLE 2 Cyanitroaniline and the following compound were reacted in a manner similar to that described in Example 2 to completely synthesize the dyes shown in Table 12 A//.

The melting point of this dye was //7~//♂°C, and the maximum absorption wavelength was 6/7 nm.

Example! syl-butoxyaniline by a method according to Example-,
The following compounds were all reacted to complete the synthesis of the dye of 2nd Copper/3. The melting point of this dye is 7.2t~/λ6. !゛0
In fact, the maximum absorption wavelength was q≦nm.

Example 6 The following compound was completely reacted with the following compound oNHCH, -<2>OCs Hu(n) by a method similar to that in Example A, to completely synthesize the dyes shown in Table λ A2j. The melting point of this dye is 727~/λ7°! °C, the maximum absorption wavelength was 9 nm.

Example 7 The following compound was reacted with the following compound in accordance with a method similar to Example 2 to completely synthesize the dye shown in Table λ Jj7. The melting point of this dye is /72~/2♂!゛0, maximum absorption wavelength Vi! It was GJ'nm.

Example ♂ The following compound was reacted with all of the following compounds by a method similar to Example λ, and the following color was determined in Table d Notification 2. Synthesized. The melting point of this dye is 72t, t~/2, J-
°C, the maximum absorption wavelength was j J 2 nm.

EXAMPLES The following compounds were reacted with p-aminoazobenzene in a manner similar to that described in Example 1 to completely synthesize the dyes shown in Table A 37. The melting point of this dye is /14t,j~/,3
The maximum absorption wavelength was 6θn.

Example 10 The following compound was reacted with the following compound according to a method similar to that of Example 1 to synthesize the pigment shown in Table 2, 1639. The melting point of this Ebisu element is 72-726°! ℃ Example // By the method according to Example 1, the following compound and the lower compound were reacted to completely synthesize the dye of Table 2, No. 16. The melting point of this dye is / /I, ,t~//
The temperature was 91.2°C, and the % maximum absorption wavelength was 609 nm.

Example/, l! According to a method similar to Example 1, the following compounds were reacted with each other to synthesize the dyes shown in Table 2, 16. The melting point of this dye is /7/,♂~/23. θ°
p in C, the maximum absorption wavelength is jg1. It was nm.

Example 3 The following compound was reacted with the following compound according to a method similar to Example 2 to synthesize the dye of the second surface layer 2. The melting point of this dye is /θg. 3~10j, 0°
0, and the maximum absorption wavelength is! /tr nm.

Example/G p-aminoazobe by a method similar to Example No. Bunsen and the following compounds NHCOOH.

By reacting with @, 2, the pigment of the surface layer 9 was totally synthesized. The melting point of this dye is 2//, 0-. 2//, J゛0 de p,
The maximum absorption wavelength was t o 9 nm 〇Example/! P-aminoazobenzene was reacted with the following compound by the method described in Example 1 to synthesize the dye of No. 2 Omoteya j7. The melting point of this dye is /6.0~166.5°
C), and the maximum absorption wavelength was j, 2♂nm.

Example 1 was reacted with p-aminoazobenzene in a manner similar to Example 1 to synthesize the dye Aj9 shown in Table 1. The melting point of the actual color chart is /lJ~/nigu℃,
What is the maximum absorption wavelength? /gnm.

Example 2 The following compounds were reacted with p-aminoazobenzene by a method based on Example 2, and the dyes shown in Table 2 A were completely synthesized. The melting point of this dye is 7.2? , ri~/, 30'
0 and the maximum absorption wavelength was j/gnm.

Example/? I) All of the following compounds were reacted with p-aminoazobenzene according to the Kita method according to Example 1 to synthesize dyes shown in Table I6≦-. The melting point of this dye is 10. Z, 3~・103.
At θ°0 and υ, the maximum absorption wavelength is! / It was evening nm.

Example 9 The following compound was reacted with the following compound by a method according to Example 1 to completely synthesize the dye shown in Table 2, 46g. The melting point of this dye is 73! ~/! ? , J°
If it is 0, the maximum absorption wavelength is! / (5' nm).

Example 20 A dye for the second surface layer g was synthesized by reacting all of the following compounds with each other by a method similar to Example 20. The melting point of this dye is 99. J~/θo'.

So, it was.

Example, 2/ All of the following compounds were reacted with each other by a method similar to Example 2 to obtain the dye of Table a, zl. Synthesized. The melting point of this dye is /, 2/, θ~/, 2/J
It was -・ at ℃.

Example 22 Dye 7 in Table 1623 was synthesized by combining p-aminoazobenzene with the following compound k)i, ratio) according to the method described in Example A. The melting point of this dye is /3. ? , ,f~/,I9J'
O-,,'--xrrx=ki was there.

EXAMPLES The following compound and the following chemical substances were reacted to synthesize the dye shown in Table 2 in accordance with the method described in Example 1. The melting point of this dye is //a,j~//7. ．． 2
At C, the large absorption wavelength was t/2 nm.

Example 2 A dye having a diameter of mm' tθ was synthesized by reacting all of the following compounds with each other according to the method described in Example 2. The melting point of this dye is 2r,j~9 daC,
What is the maximum absorption wavelength? /4t nm.

Example 2! Compound below H2N-G IJ == NG N H.

/, 0!17. @ Hydrochloric acid 3-1 water, 2jnd. ~! °c
In a nitrous furnace, add 0.7 g gold of soda and stir at the same temperature for 4 hours.
, G o O, H, , (n) 2.96 jl was added to a mixture of 30 d of N-methylpyrrolidone, reacted at 10° or less for 6 hours, and water 704 was added to form a precipitate. After being taken in a furnace, it was purified by a chromatographic method to obtain a color spectrum of No. λ Omoteya Octopus. The melting point of this dye is 232~λJJ''Q,
What is the maximum absorption wavelength? /6 nm.

Example-26 Example 2! The following compound was reacted with the following compound according to a method similar to the above, to synthesize a colored kite shown in Table λ, 162. The melting point of this dye is /l~/77°0 Example-! 2 Example-2! By a method according to the method, the above compound and the following ft, compound ? Let it react, the Ωth surface layer? The melting point of 770 pigment colors synthesized is 2.2~2.2t
, 7゛0, maximum absorption wavelength is /s / / nm
Met.

and the following compounds were reacted to synthesize the dye color of the 1st 2nd surface layer/θθ. The melting point of this Ebisu element is 23/, j~, 23
-d, and the maximum absorption wavelength was j4t(!' nm).

By the method according to Example d! ') By reacting p-butoxyaniline with the following compound, the dye shown in Table 12 AI/2 was synthesized. The melting point of the dye was C2/~, 2.29°C, R large absorption The wavelength was g j j , nln.

Example JO The following compound u was reacted with the following compounds in a manner similar to Example 1 to completely synthesize the dye AN shown in Table λ A//l. The melting point of this dye is 2/θ! The maximum absorption wavelength was 66 nm.

[Brief explanation of drawings]

Figure 1 and Figure 1! The figure is a schematic cross-sectional view of the example system of the present invention in a state where no voltage is applied. A spectral characteristic diagram of the example system of the present invention used, and Fig. g is a schematic cross-sectional view of the voltage applied state of the example system of the present invention. ...Pleochroic dye molecule Applicant Mitsubishi Chemical Industries, Ltd. Hitachi, Ltd. Agent Patent attorney Yo Hase - 7 others Figure 1 Figure 2 Yoshinaga Nagishi (nm) Figure 73 Yonaga (nA) ) 4 Nagi Rincho (Nishiki) Figure 5 Man (:1 Figure 11 Continued from page 1 0 Inventor Junko Iwanami Mitsubishi Chemical Industries, Ltd. Research Center, 1000 Kamoshida-cho, Midori-ku, Yokohama ■Applicant Mitsubishi Kasei Kogyo Co., Ltd. 2-5-2 Marunouchi, Chiyoda-ku, Tokyo

Claims (4)

[Claims] (1) General formula [■] is a hydrogen atom, an alkyl group, an alkoxyalkyl group, an aryloxyalkyl group, a dialkylaminoalkyl group,
Arylaminoalkyl group, cycloalkyl group, alkoxy group, alkoxyalkoxy group, aryl group, halogen represent hydrogen atom, halogen atom, alkyl group, alkoxy group, acylamino group, cyan group, and zl and l and 7 and 2 are , may be linked to each other to form an aromatic @total structure. Y represents the acid R' alkyl group, and R' is connected to 24-l to ff
1k may be formed. ul, ul is a hydrogen atom, a halogen atom, a methyl group, a methoxy group, an ethochroic dye. (2) In general formula (1), D' represents an aromatic group that does not contain 2g, and zY to Z9 are hydrogen atoms,
halogen atom, alkyl group, alkoxy group, acylamino group, cyanide group, and z7 and z8 may be connected to each other to form an aromatic ring). sex pigment. (3) In the general formula [1], Dl represents U' hydrogen atom or an alkyl group, zjo to zls represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an acylamino group, or a cyano group, and zl.佳Hi z′1, Z”
and U Z″Z hiIc Z” and U Z” tri
They may be connected to each other to form a complete aromatic ring, and 210 to z
′! may be linked to R' to form a nitrogen-containing it shadow. Ul
1%U' represents a hydrogen atom, halogen atom, methyl group, methoxy group, or ethoxy group, xl represents a hydrogen atom, an alkyl group, an alkoxy-alkyl group, an aryloxyalkyl group, an alkylaminoalkyl group, or a dialkylaminoalkyl group. , arylaminoalkyl group, cycloalkyl group, alkoxy group, alkoxyalkoxy group, aryl group, and halogen atom. ) The azo pleochroic dye according to claim 1. (4) General formula [I] Ruaminoalkyl group, arylaminoalkyl group, cycloalkyl group, alkoxy group, alkoxyalkoxy group, aryl group, halogen is hydrogen atom, halogen atom, alkyl group, alkoxy group, acylamino group, cyanogen Show the fund and also zl and 2! Also, 2' and 2' may be connected to each other to form a complete aromatic ring. Y represents an acid atom or a -N- group, R1 represents a hydrogen atom or an alkyl group, and R1 may be linked to z4 to z6 to form a complete ring. υ and υ represent a hydrogen atom, a halogen atom, a methyl group, a methoxy group, and an ethoxy group, and D' and D2 represent an aromatic group that does not include all ionic groups. ) 0 liquid crystal composition containing an azo pleochroic dye 1 Of course.