JP2002302675A - Liquid crystal composition, liquid crystal device using the same, and azo compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a liquid crystal composition which exhibits a high dichroic ratio and, when used for a display element, can improve the contrast of display. SOLUTION: This liquid crystal composition contains a compound represented by formula (1) [wherein D<1> and D<2> are each a chromophore; L<1> and L<2> are each a linking group; n1 and n2 are each 0 or 1; and Q is a divalent group represented by formula (Q) (wherein X and Y are each nitrogen atom or CH; n is an integer of 1-5; each of X and Y, being present in a number of 2n as the total, may be the same or different from each other provided at least one of them is nitrogen atom; and R<1> to R<8> are each hydrogen atom or a substituent)].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel liquid crystal device, particularly to a guest-host type liquid crystal device, and more particularly to a liquid crystal composition and a novel azo compound which can be used for a guest-host type liquid crystal device.

[0002]

2. Description of the Related Art Many types of liquid crystal elements have been proposed (for example, edited by the 142nd Committee of the Japan Society for the Promotion of Science, Liquid Crystal Device Handbook, Nikkan Kogyo Shimbun, 1989).
Year). For example, in a guest-host type liquid crystal element, a liquid crystal composition in which a dichroic dye is dissolved in a liquid crystal is sealed in a cell, an electric field is applied to the cell, and the dichroic dye is adjusted according to the movement of the liquid crystal by the electric field. In this method, the display is performed by changing the orientation of the cell and changing the light absorption state of the cell. This guest-host method is expected as a reflection type liquid crystal element in that bright display is possible. Here, as for the guest host method, for example, “Handbook of Liquid Crystal
s "(B. Bahadur, D. Demus, J. Goodby, GW Gray,
HW Spiess, V. Vill, Vol. 2A, Wiley-VCH, 1998
), Chapter 3.4, pages 257-302. For dichroic dyes used in liquid crystal devices, see “Dichroic Dyes for Liquid Crystal Display”.
(By AVIvashchenko, CRC, 1994) has a detailed description.

A dichroic dye used in a liquid crystal element is required to have appropriate absorption characteristics, high order parameters, and high performance such as high solubility and durability in a host liquid crystal. Here, the order parameter S is given by S = (3) when the molecular long axis of a molecule which is thermally fluctuated is inclined with respect to the director by a time average deviation angle θ.
cos ² θ-1) / 2. When S = 0.0, it indicates that the molecule is in a completely disordered state.
A value of 1.0 indicates that the molecules are aligned with the molecular long axis aligned with the direction of the director. Conventional 2
The chromatic dye does not give a sufficiently high order parameter, and as a result, the display contrast in the guest-host type liquid crystal display device has been reduced.

[0004]

SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned problems, and a liquid crystal composition exhibiting a high two-color ratio and capable of improving display contrast when used in a display device. It is an object to provide a liquid crystal element. Another object of the present invention is to provide a novel azo compound useful as a dichroic dye, particularly, a novel azo compound giving a high order parameter.

[0005]

Means for Solving the Problems In order to solve the above problems, the liquid crystal composition of the present invention is characterized by containing a compound represented by the following general formula (1).

[0006]

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In the formula, D ¹ and D ² each independently represent a chromophore; L ¹ and L ² each independently represent a linking group;
¹ and n ² each independently represent 0 or 1, and Q represents a divalent group represented by the following general formula (Q).

[0008]

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In the formula, X and Y each represent a nitrogen atom or CH, and n represents an integer of 1 to 5. 2n in total
X and Y may be the same or different, but at least one is a nitrogen atom. R
^{1 to} R ⁸ each independently represent a hydrogen atom or a substituent;
Two of ^{1 to} R ⁸ bonded to adjacent carbon atoms may be bonded to each other to form a ring. When n is 2 or more, a plurality of R ^{1 to} R ⁸ may be the same or different.

In the liquid crystal composition of the present invention, D ¹ and D ² are preferably a chromophore of an azo dye or an anthraquinone dye.

In the liquid crystal composition of the present invention, the compound represented by the general formula (1) is preferably represented by the following general formula (2).

[0012]

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[0013] In the formula, Ar ¹ to Ar ⁴ of the substituted or unsubstituted each independently represents an aryl group or a heteroaryl group, L ¹ and L ² each independently represent a linking group, n ¹
And n ² each independently represent 0 or 1, and Q represents a divalent group represented by the following general formula (Q).

[0014]

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In the formula, X and Y each represent a nitrogen atom or CH, and n represents an integer of 1 to 5. 2n in total
X and Y may be the same or different, but at least one is a nitrogen atom. R
^{1 to} R ⁸ each independently represent a hydrogen atom or a substituent;
Two of ^{1 to} R ⁸ bonded to adjacent carbon atoms may be bonded to each other to form a ring. When n is 2 or more, a plurality of R ^{1 to} R ⁸ may be the same or different.

In the liquid crystal composition of the present invention, the divalent group represented by Q in the general formulas (1) and (2) is represented by the following general formulas (Q-1) to (Q-3). And preferably contains any divalent group represented by the following general formula (Q-
More preferably, it is any of the divalent groups represented by 1) to (Q-3).

[0017]

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Wherein R ^{11 to} R ¹⁸ , R ^{21 to} R ²⁸ and R ³¹
To R ³⁸ each independently represent a hydrogen atom or a substituent,
Two of R ^{11 to} R ¹⁸ , R ^{21 to} R ^28, and R ^{31 to} R ³⁸ which are bonded to adjacent carbon atoms may be bonded to each other to form a ring.

The compound represented by the general formula (1) is preferably a compound represented by any of the following general formulas (3) to (5).

[0020]

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In the formula, Ar ^{1 to} Ar ⁴ each independently represent a substituted or unsubstituted aryl group or heteroaryl group.

In order to solve the above problems, a liquid crystal device according to the present invention is characterized by having a liquid crystal layer containing the liquid crystal composition according to the present invention. In order to solve the above problems, the azo compound of the present invention is represented by the following general formula (6).

[0023]

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In the formula, Ar ^{1 to} Ar ⁴ each independently represent a substituted or unsubstituted aryl or heteroaryl group, L ¹ and L ² each independently represent a linking group, and n ¹ and n ² Each independently represents 0 or 1, and R ^{11 to} R ¹⁸
And R ^{21 to} R ²⁸ each independently represent a hydrogen atom or a substituent, and two of R ^{11 to} R ¹⁸ and R ^{21 to} R ²⁸ bonded to adjacent carbon atoms are bonded to each other to form a ring. It may be formed.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. In this specification, “to” indicates a range including numerical values described before and after it as a minimum value and a maximum value, respectively.

The liquid crystal composition of the present invention has the following general formula (1)
Characterized by containing a compound represented by the formula: The compound represented by the following general formula (1) has a function as a dichroic dye, gives a high order parameter, and contributes to an improvement in the dichroic ratio of the liquid crystal composition.

[0026]

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In the general formula (1), D ¹ and D ²
Each independently represents a chromophore. About the chromophore,
There is no particular limitation, and examples thereof include chromophores such as azo dyes, anthraquinone dyes, perylene dyes, merocyanine dyes, azomethine dyes, phthaloperylene dyes, indigo dyes, azulene dyes, dioxazine dyes, and polythiophene dyes. Specifically, "Dichroic Dyes for Liqu
id Crystal Display ”(by AV Ivashchenko, CRC
Co., 1994). Preferred are chromophores of azo dyes, anthraquinone dyes or perylene dyes, and particularly preferred are chromophores of azo dyes or anthraquinone dyes.

When the chromophore is an azo dye chromophore, the kind thereof is not particularly limited, and may be any chromophore such as a monoazo dye, a bisazo dye, a trisazo dye, a tetrakisazo dye or a pentakisazo dye. . Preferred are chromophores of monoazo dyes, bisazo dyes and trisazo dyes. A chromophore of an azo dye having a ring structure is preferable, for example, an aromatic group (benzene ring, naphthalene ring, etc.) and / or a heterocyclic ring (quinoline ring, pyridine ring, thiazole ring, benzothiazole ring, oxazole ring, benzoxazole ring) , An imidazole ring, a benzimidazole ring, a pyrimidine ring, etc.).

When the chromophore is a chromophore of an anthraquinone dye, a chromophore of an anthraquinone dye having a substituent containing at least one of an oxygen atom, a sulfur atom and a nitrogen atom is preferable, for example, alkoxy, aryloxy, alkylthio, An anthraquinone dye chromophore having an arylthio, alkylamino, or arylamino group as a substituent is preferable. The number of substituents on the anthraquinone ring of the substituent is not particularly limited, but is preferably di-, tri-, or tetrakis-substitution, and particularly preferably di- or tri-substitution. The position of the substituent on the anthraquinone ring is not particularly limited, but is preferably 1,4.
Di-substitution, 1,5-di substitution, 1,4,5-tri substitution,
1,2,4-position tri-substitution, 1,2,5-position tri-substitution, 1,
It is a tetra-substituted structure at the 4,5,8-position or a tetra-substituted 1,2,5,6-position.

In the general formula (1), L ¹ and L ²
Each independently represents a linking group. n ¹ and n ² each represent 0 or 1, and when n ¹ and n ² are 0, Q is D ¹
And D ² by a single bond. The linking groups represented by L ¹ and L ² each consist of at least one atom selected from a carbon atom, a nitrogen atom, a sulfur atom and an oxygen atom, or an atomic group containing at least one atom. As the linking group, an alkylene group having 1 to 20 carbon atoms (for example, a methylene group, an ethylene group, a propylene group,
A butylene group, a pentylene group, a 1,4-cyclohexylene group), an arylene group having 6 to 30 carbon atoms (e.g., p-phenylene group, o-phenylene group, m-phenylene group,
1,4-naphthylene group, 1,3-naphthylene group, 4,
4'-biphenylene group, 4,4'-2,2'-dimethylbiphenylene group, 4,4'-2,2'-dimethoxybiphenylene group, 4,4'-2,2'-dichlorobiphenylene group), carbon Alkenylene groups of 2 to 20 (eg ethenylene group), alkynylene groups of 2 to 20 carbon atoms (eg ethinylene group), amide group, ester group, sulfamide group, sulfonate group, ureido group, sulfonyl group, sulfinyl Group, thioether group, ether group,
1 selected from a carbonyl group, -NR- (where R represents a hydrogen atom, an alkyl group or an aryl group) and a divalent heterocyclic group (for example, a 2,6-pyridinylene group)
1 or more carbon atoms composed of a combination of two or more species
60 linking groups.

These linking groups may be further substituted with a substituent.
^The substituents exemplified as the substituents represented by ^{1 to} R ⁸ are exemplified.

The compound represented by the general formula (1) is represented by n
¹ and n ² are 0, or n ¹ and n ² are 1 and L ¹ and L ² are an alkylene group, an arylene group, an alkynylene group, an ether group (—O—) and a carbonyl group (—C (= Preferably, the linking group contains at least one of O)-). Further, n ¹ and n ² is 0 or n ¹ and n ² is 1 and the L ¹ and L ² is an alkylene group, an ether group (-O-) and / or a carbonyl group (-C (= More preferably, the linking group contains O)-).

In the general formula (1), Q represents a divalent group represented by the following general formula (Q).

[0034]

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In the general formula (Q), R ^{1 to} R ⁸ each independently represent a hydrogen atom or a substituent. Examples of the substituent include a halogen atom (e.g., chlorine, bromine, iodine, fluorine); a mercapto group; a cyano group; a carboxyl group; a phosphoric acid group; a sulfo group; a hydroxy group; -8, more preferably 2-5 carbon atoms
(E.g., methylcarbamoyl group, ethylcarbamoyl group, morpholinocarbonyl group); a sulfamoyl group having 0 to 10, preferably 2 to 8, more preferably 2 to 5 carbon atoms (e.g., methylsulfo group) Famoyl group, ethylsulfamoyl group, piperidinosulfonyl group); nitro group; unsubstituted alkyl group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms (for example, Methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group); a substituted alkyl having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms. Groups (for example, hydroxymethyl, trifluoromethyl, benzyl, carboxyethyl, ethoxycarbonylmethyl, Ruaminomechiru group); a carbon number 2
18, preferably a substituted or unsubstituted alkenyl group having 3 to 10 carbon atoms, more preferably 3 to 5 carbon atoms (for example,
Vinyl group, phenylethenyl group); having 2 to 18 carbon atoms, preferably 3 to 10 carbon atoms, more preferably 3 to 5 carbon atoms
Substituted or unsubstituted alkynyl group (for example, ethynyl group, phenylethynyl group); a substituted or unsubstituted cyclic aliphatic group having 2 to 18 carbon atoms, preferably 3 to 10 carbon atoms, and more preferably 3 to 5 carbon atoms Hydrocarbon group (for example, 1-cyclohexenyl group, cyclohexyl group, cyclopentyl group, 4-methylcyclohexyl group, 4-ethylcyclohexyl group, 4-propylcyclohexyl group, 4-butylcyclohexyl group);

C 1-20, preferably C 1-1
0, more preferably an alkoxy group having 1 to 8 carbon atoms (for example, methoxy group, ethoxy group, 2-methoxyethoxy group, 2-phenylethoxy group); 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms, and Preferably 6-1 carbon atoms
0 aryloxy group (for example, phenoxy group, p-methylphenoxy group, p-chlorophenoxy group, naphthoxy group); having 1 to 20 carbon atoms, preferably 2 to 12 carbon atoms;
More preferably, an acyl group having 2 to 8 carbon atoms (for example, an acetyl group, a benzoyl group, or a trichloroacetyl group); an acyloxy group having 1 to 20 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 8 carbon atoms. (E.g., acetyloxy group, benzoyloxy group);
Preferably it has 2 to 12 carbon atoms, more preferably 2 carbon atoms.
To 8 acylamino groups (for example, an acetylamino group);
C1-C20, preferably C1-C10, more preferably C1-C8 sulfonyl group (e.g., methanesulfonyl group, ethanesulfonyl group, benzenesulfonyl group); C1-C20, preferably carbon Equations 1 to 10,
More preferably, a sulfinyl group having 1 to 8 carbon atoms (e.g., methanesulfinyl group, ethanesulfinyl group, benzenesulfinyl group); 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms Sulfonylamino group (for example, methanesulfonylamino group,
Ethanesulfonylamino group, benzenesulfonylamino group); amino group; having 1 to 20 carbon atoms, preferably 1 carbon atom
To 12, more preferably a substituted amino group having 1 to 8 carbon atoms (for example, a methylamino group, a dimethylamino group, a benzylamino group, an anilino group, a diphenylamino group); 10, more preferably an ammonium group having 3 to 6 carbon atoms (eg, a trimethylammonium group, a triethylammonium group); a hydrazino group having 0 to 15 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms (For example, a trimethylhydrazino group);

C 1 -C 15, preferably C 1 -C 1
0, more preferably a ureido group having 1 to 6 carbon atoms (e.g., ureide group, N, N-dimethylureido group); 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. (E.g., a succinimide group); an alkylthio group having 1 to 20, preferably 1 to 12, and more preferably 1 to 8 carbon atoms (e.g., a methylthio group, an ethylthio group, and a propylthio group);
An arylthio group having 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms, more preferably 6 to 10 carbon atoms (for example, phenylthio group, p-methylphenylthio group, p-chlorophenylthio group, 2-pyridylthio group, naphthylthio Group); an alkoxycarbonyl group having 2 to 20 carbon atoms, preferably 2 to 12 carbon atoms, more preferably 2 to 8 carbon atoms (eg, methoxycarbonyl group, ethoxycarbonyl group, 2-benzyloxycarbonyl group); 6-2
0, preferably an aryloxycarbonyl group having 6 to 12 carbon atoms, more preferably 6 to 10 carbon atoms (for example, a phenoxycarbonyl group); 6 to 20 carbon atoms, preferably 6 to 15 carbon atoms, more preferably 5 to 15 carbon atoms 6 to 10 substituted or unsubstituted aryl groups (for example, phenyl group, naphthyl group, p-carboxyphenyl group, p-nitrophenyl group, 3,5-dichlorophenyl group, p-cyanophenyl group, m-fluorophenyl group , A p-tolyl group); a substituted or unsubstituted heterocyclic group having 1 to 20 carbon atoms, preferably 2 to 10 carbon atoms, more preferably 4 to 6 carbon atoms (for example, pyridyl group, 5-methylpyridyl group, Thienyl group, furyl group, morpholino group, tetrahydrofurfuryl group).

Further, two of R ^{1 to} R ⁸ bonded to adjacent carbon atoms may be bonded to each other to form a ring. The formed ring includes a benzene ring and a naphthalene ring.

Each of R ^{1 to} R ⁸ is preferably a hydrogen atom, a halogen atom, an alkyl group, an aryl group or an alkoxy group, and is preferably a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a trifluoromethyl group, a phenyl group or It is more preferably a trifluoromethoxy group, and particularly preferably a hydrogen atom.

In the general formula (Q), X and Y represent a nitrogen atom or CH, and n represents an integer of 1 to 5. n is preferably 1 to 3. 2n in total
X and Y may be the same or different, but at least one is a nitrogen atom.

The Q is represented by the following general formulas (Q-1) to (Q-
It preferably contains a divalent group represented by any of 3), and more preferably one of the following general formulas (Q-1) to (Q-3).

[0042]

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In the general formulas (Q-1) to (Q-3), R ^{11 to} R ¹⁸ , R ^{21 to} R ²⁸ and R ^{31 to} R ³⁸ each independently represent a hydrogen atom or a substituent; R ^{11 to} R ¹⁸ , R
Two of R ^{21 to} R ²⁸ and R ^{31 to} R ³⁸ bonded to adjacent carbon atoms may be bonded to each other to form a ring. The substituents represented by R ^{11 to} R ¹⁸ , R ^{21 to} R ²⁸ and R ^{31 to} R ³⁸ are the same as the substituents represented by R ^{1 to} R ⁸ ,
The same applies to preferred specific examples. R ^{11 to} R ¹⁸ , R
²¹ two of to R ²⁸ and R ³¹ to R ³⁸ for also rings formed by bonding, it is the same as those for R ¹ to R ^8.

Among the compounds represented by the general formula (1), a compound represented by the following general formula (2) is preferable.

[0045]

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In the general formula (2), Q has the same meaning as Q in the general formula (1), and the preferred range is also the same.

In the general formula (2), Ar ^{1 to} Ar ⁴
Each independently represents a substituted or unsubstituted aryl group or heteroaryl group. The aryl group includes both those having a single ring structure and those having a condensed ring structure. An aryl group having 2 to 20 carbon atoms is preferable, and specifically, an aryl group including a benzene ring, a naphthalene ring, and an anthracene ring is preferable. The heteroaryl group includes both a single ring structure and a condensed ring structure. As the heteroaryl group, a heteroaryl group having 2 to 20 carbon atoms is preferable, and a pyridine ring, a quinoline ring, an isoquinoline ring, a pyrimidine ring, a pyrazine ring, a thiophene ring, a furan ring, an oxazole ring, a thiazole ring, an imidazole ring, and a pyrazole ring A group containing a ring, an oxadiazole ring, a thiadiazole ring, or a triazole ring, or a heterocyclic ring formed by condensing two or more of these heteroaromatic rings or one or more of these heteroaromatic rings with the aromatic ring of the aryl group described above. And a group containing a condensed ring.

When Ar ^{1 to} Ar ⁴ have a substituent, examples of the substituent include those described above as the substituents represented by R ^{1 to} R ⁸ , and -N = N-Ar ⁵ and-.
^{N = N-Ar 6 -N =} N-Ar 7 azo group such groups are exemplified. Here, Ar ⁵ , Ar ⁶ , and Ar ⁷ are Ar ¹ to Ar ¹ shown above.
Synonymous with Ar ⁴ , both specific examples and examples of substituents are Ar ^{1 to} A
It is the same as those shown in r ^4. When Ar ^{1 to} Ar ⁴ have a substituent, the substituent is preferably a halogen atom, an alkyl group, an aryl group or an alkoxy group, and is preferably a fluorine atom, a chlorine atom, a methyl group, a trifluoromethyl group, a phenyl group or a trialkyl group. Preferably it is a fluoromethoxy group. Further, as the substituent of Ar ^{1 to} Ar ⁴ ,
-N = N-Ar ⁵ group and -N = N-Ar ⁶ -N = NA
An r ⁷ group is also preferable, and a compound having a polyazo dye structure is also preferable.

In the general formula (2), n ¹ , n ² , L ¹ and L ² have the same meanings as those in the general formula (1). In the general formula (2), n ¹ is 0 and Ar ¹
Is preferably a nitrogen atom. In the general formula (2), n ² is 1, Y bonded to L ² is CH, and L ² is a carbonyl group —C
It is preferably a linking group containing (＝ O) — and / or an ether group (—O—).

Among the compounds represented by the general formula (2), n ¹ and n ² are 0 and Q is the same as that of the general formula (Q-
1) to the divalent group of any of (Q-3), and R ¹
Compounds in which all of R ⁸ to R ⁸ are hydrogen atoms, that is, compounds represented by any of the following formulas (3) to (5) are particularly preferred.

[0051]

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In the general formulas (3) to (5), Ar
^{1 to} Ar ⁴ each independently represent a substituted or unsubstituted aryl group or heteroaryl group. The aryl group and the heteroaryl group are as defined above, and the preferred ranges are also the same.

The compound represented by the general formula (2) includes a compound represented by the following general formula (6).

[0054]

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[0055] In the formula, Ar ¹ to Ar ⁴ of the substituted or unsubstituted each independently represents an aryl group or a heteroaryl group, L ¹ and L ² each independently represent a linking group, n ¹
And n ² each independently represent 0 or 1, and R ^{11 to} R
¹⁸ and R ^{21 to} R ²⁸ each independently represent a hydrogen atom or a substituent, and two of R ^{11 to} R ¹⁸ and R ^{21 to} R ²⁸ bonded to adjacent carbon atoms are bonded to each other to form a ring. May be formed. In the general formula (6), Ar ¹
-Ar ⁴ , R ¹¹ -R ¹⁸ and R ²¹ -R ²⁸ are as defined for each group in the general formulas (2) and (Q-2), and specific examples and preferred ranges thereof The same is true for In the general formula (6), n ¹ and n ² are preferably 0.

Specific examples (exemplary compounds 1 to 77) of the compound represented by the general formula (1) are shown below, but the present invention is not limited by the following specific examples.

[0057]

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[0058]

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[0059]

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[0060]

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[0061]

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[0062]

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[0063]

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[0064]

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The compound represented by the general formula (1) is
"Dichroic Dyes for Liquid CrystalDisplay" (AV
Ivashchenko, CRC, 1994), "Review Synthetic Dyes" (Horiguchi Hiroshi, Sankyo Shuppan, 1968) and the methods described in the references cited therein can be synthesized.

In the liquid crystal composition of the present invention, one kind of the compound represented by the general formula (1) may be used alone, or a plurality of kinds may be mixed and used. When a plurality of types of dyes are mixed, two or more of the compounds represented by the general formula (1) may be used as a mixture, or may be used in combination with the compound represented by the general formula (1). May be used in combination. Examples of dichroic dyes that can be used in combination include, for example, “Dichroic Dyes for Liquid Crystal Display”
(AV Ivashchenko, CRC, 1994) can be used. For example, when the liquid crystal composition of the present invention is used for black display, it is necessary to absorb light in the entire visible region, and it is preferable to use a mixture of a plurality of dichroic dyes.

The host liquid crystal that can be used in the liquid crystal composition of the present invention is not particularly limited as long as it can coexist with the compound represented by the general formula (1). For example, a nematic phase or a smectic phase can be used. The following liquid crystal compounds can be used. Specific examples thereof include an azomethine compound, a cyanobiphenyl compound, a cyanophenyl ester, a fluorine-substituted phenyl ester, a cyclohexanecarboxylic acid phenyl ester, a fluorine-substituted cyclohexanecarboxylic acid phenyl ester, a cyanophenylcyclohexane, a fluorine-substituted phenylcyclohexane, a cyano-substituted phenylpyrimidine, Fluorine-substituted phenylpyrimidine, alkoxy-substituted phenylpyrimidine, fluorine-substituted alkoxy-substituted phenylpyrimidine, phenyldioxane, tolan compound,
Fluorine-substituted tolan compounds, alkenylcyclohexylbenzonitrile, and the like. Liquid Crystal Device Handbook (edited by the 142nd Committee of the Japan Society for the Promotion of Science, Nikkan Kogyo Shimbun, 1989), pp. 154-192 and 7
The liquid crystal compounds described on pages 15 to 722 can be used. A fluorine-substituted host liquid crystal suitable for driving a TFT can also be used.

The liquid crystal composition of the present invention has the purpose of adjusting the physical properties of the host liquid crystal to a desired range (for example, to adjust the temperature range of the liquid crystal phase to a desired range).
A compound having no liquid crystallinity may be added. Further, compounds such as a chiral compound, an ultraviolet absorber, and an antioxidant may be contained. Such additives are described in, for example, "Liquid Crystal Device Handbook" (edited by the 142nd Committee of the Japan Society for the Promotion of Science, Nikkan Kogyo Shimbun, 1989), 199-20.
TN and STN chiral agents described on page 2.

In the liquid crystal composition of the present invention, the content of the host liquid crystal and the compound represented by the general formula (1) is not particularly limited, but the content of the compound represented by the general formula (1) is not limited. Is 0.1 to the content of the host liquid crystal.
It is preferably 15% by mass, particularly preferably 0.5 to 6% by mass.

The liquid crystal composition of the present invention can be prepared by dissolving the compound represented by the general formula (1) in a host liquid crystal. The dissolution can be performed using mechanical stirring, heating, ultrasonic waves or a combination thereof.

The liquid crystal device of the present invention is a liquid crystal device having a liquid crystal layer containing the liquid crystal composition of the present invention. The liquid crystal element of the present invention can be composed of, for example, a pair of electrode substrates and a liquid crystal layer containing the liquid crystal composition of the present invention sandwiched between the pair of electrode substrates. As the electrode substrate, one obtained by forming an electrode layer on a substrate usually made of glass or plastic can be used. Examples of the plastic substrate include an acrylic resin, a polycarbonate resin, and an epoxy resin. For the substrate, see, for example, 218-23 of “Liquid Crystal Device Handbook” (edited by the 142nd Committee of the Japan Society for the Promotion of Science, Nikkan Kogyo Shimbun, 1989).
Those described on page 1 can be used. The electrode layer formed on the substrate is preferably a transparent electrode layer. For example, indium oxide, indium tin oxide (ITO),
It can be formed from tin oxide or the like. For the transparent electrode, see, for example, “Liquid Crystal Device Handbook” (edited by the 142nd Committee of the Japan Society for the Promotion of Science, Nikkan Kogyo Shimbun, 1989).
Year)), pages 232 to 239.

It is preferable that an alignment-treated layer (alignment film) is formed on the surface of the substrate in contact with the liquid crystal layer. As the alignment treatment, for example, a method of applying and aligning a quaternary ammonium salt, a method of applying polyimide and aligning by rubbing treatment, a method of aligning by depositing SiO _x in an oblique direction, and further, photoisomerization An alignment method by light irradiation used is exemplified. For the alignment film, for example, see “Liquid Crystal Device Handbook” (edited by the 142nd Committee of the Japan Society for the Promotion of Science, Nikkan Kogyo Shimbun, 1989).
Years), pp. 240-256.

In the liquid crystal device of the present invention, for example, a pair of substrates are opposed to each other at a distance of 1 to 50 μm via a spacer or the like, and the liquid crystal composition of the present invention is injected into a space formed between the substrates. Can be produced. About the spacer, for example, "Liquid crystal device handbook"
(The 142nd Committee of the Japan Society for the Promotion of Science, Nikkan Kogyo Shimbun,
1989), pp. 257-262.

The liquid crystal element of the present invention can be driven by a simple matrix driving method or an active matrix driving method using a thin film transistor (TFT) or the like. For the driving method, for example, see “Liquid Crystal Device Handbook” (edited by the 142nd Committee of the Japan Society for the Promotion of Science,
The details are described on pages 387 to 460 of Nikkan Kogyo Shimbun, 1989) and can be used as a driving method of the liquid crystal element of the present invention.

The liquid crystal device of the present invention can be used for a liquid crystal display. Although there is no particular limitation on the method, for example, “Liquid Crystal Device Handbook” (edited by the 142nd Committee of the Japan Society for the Promotion of Science, Nikkan Kogyo Shimbun, 19
89), page 309, guest-host system, homogeneous alignment, homeotropic alignment, W
focal-conic orientation and homeotropic orientation as a hite-Taylor type (phase transition), Su
combination with per Twisted Nematic (STN), combination with ferroelectric liquid crystal (FLC), and "reflective color LCD comprehensive technology" (supervised by Tatsuo Uchida,
Helmier type GH mode, １ ／ wavelength plate type GH mode, and two-layer type described in Chapter 2-1 (GH mode reflection type color LCD), pages 15 to 16 of CMC Corporation, 1999). GH mode, phase transition type G
H mode, polymer dispersed liquid crystal (PDLC) type GH mode, and the like.

Further, the liquid crystal device of the present invention is disclosed in
67990, 10-239702, 10-13
No. 3223, No. 10-339881, No. 11-524
No. 11, 11-64880, JP-A-2000-221
It can be used for a laminated GH mode described in various publications such as 538, and a GH mode liquid crystal display using microcapsules described in Japanese Patent Application Laid-Open No. 11-24090. Further, Japanese Patent Application Laid-Open No. 6-235
No. 931, No. 6-235940, No. 6-265859
Nos. 7-56174, 9-146124, 9
No. 197388, No. 10-20346, No. 10-3
No. 1207, No. 10-31216, No. 10-3123
No. 1, No. 10-31232, No. 10-31233,
No. 10-31234, No. 10-82986, No. 10
-90674, 10-11113, 10-1
No. 11523, No. 10-123509, No. 10-12
No. 3510, No. 10-206581, No. 10-253
No. 993, No. 10-268300, No. 11-1492
No. 52, JP-A-2000-2874, etc., can be used for the reflection type liquid crystal display.
Also, JP-A-5-61025 and JP-A-5-265053
Nos. 6-3691 and 6-23061 and 5-2
Nos. 03940, 6-242423, 6-2893
No. 76, No. 8-278490, No. 9-81174, etc. can be used for a polymer dispersed liquid crystal type GH mode liquid crystal display.

In addition, the liquid crystal device of the present invention can be applied to a spatial light modulator, a light or heat writing type liquid crystal display, and the like.

[0078]

The present invention will be described more specifically with reference to the following examples. Materials, reagents, ratios, operations, and the like shown in the following examples can be appropriately changed without departing from the gist of the present invention. Therefore, the scope of the present invention is not limited to the following specific examples. <Example 1: Synthesis of exemplified compound 10>

[0079]

Embedded image

1.35 g of the raw material (1) was dissolved in 30 mL of acetic acid, and 3 mL of concentrated hydrochloric acid was added under ice-cooling. Under ice-cooling, 0.76 g of sodium nitrite was added, and the mixture was stirred for 1 hour. The obtained reaction solution was treated at room temperature with the starting material (2) under 3.
36 g of tetrahydrofuran solution was dropped into 40 mL and stirred for 10 hours. Water was added to the reaction solution, the organic matter was extracted with chloroform, dried, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel chromatography (eluent was a 10: 1 mixed solvent of chloroform and methanol). Then, 0.28 g of a target compound (exemplified compound 10) was obtained as a yellow powder. The properties of the obtained compound are shown below. Maximum absorption wavelength 520 nm (dimethylformamide) Absorption coefficient 6.6 × 10 ⁴

Example 2 1 mg of each of the compounds shown in Table 1 below was used in a commercially available liquid crystal (trade name "ZLI-1132";
E. FIG. (Manufactured by Merck) 100 mg to prepare liquid crystal compositions. Each of the obtained liquid crystal compositions was injected into a commercially available substrate for a liquid crystal cell, thereby producing a guest-host liquid crystal element. The liquid crystal cell substrate used was E.I. H. C. A glass plate (thickness 0.7 mm) on which an ITO transparent electrode layer and a polyimide alignment film (with parallel arrangement by rubbing treatment) were formed, and a cell gap of 8
μm, with an epoxy resin seal.

Each of the manufactured liquid crystal elements was irradiated with polarized light parallel to and perpendicular to the rubbing direction, and the respective absorption spectra (A‖ and A⊥) were measured by Shimadz.
It was measured by uUV3100. A at the maximum absorption wavelength
From ‖ and A⊥, the order parameter S was determined for each according to Equation 1 below. The determined order parameter S is shown together with λmax (nm). Formula 1 S = (A‖−A⊥) / (A‖ + 2 × A⊥)

[0083]

[Table 1]

[0084]

Embedded image

From the results shown in Table 1, the liquid crystal composition using the compound represented by the general formula (1) exhibited higher order parameters and a higher two-color ratio than the conventionally known comparative dye 1. Found to give.

Example 3 A commercially available fluorine-based liquid crystal (trade name: ZLI-4792; E. Mer.
ck) and the order parameter S was measured by the same operation as in Example 2 to find that S = 0.81. It has been found that when the compound represented by the general formula (1) is used, a liquid crystal composition exhibiting high order parameters can be obtained even when a fluorine-based host liquid crystal is used.

[0087]

According to the present invention, it is possible to provide a liquid crystal composition and a liquid crystal element which exhibit a high two-color ratio and which can improve display contrast when used in a display element. Further, according to the present invention, a novel azo compound useful as a dichroic dye, in particular, a novel azo compound giving a high order parameter can be provided.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) G02F 1/13 500 G02F 1/13 500

Claims (8)

[Claims] 1. A liquid crystal composition comprising a compound represented by the following general formula (1). Embedded image (Wherein D ¹ and D ² each independently represent a chromophore;
¹ and L ² each independently represent a linking group, and n ¹ and n ²
Each independently represents 0 or 1, and Q represents a divalent group represented by the following general formula (Q). ) (In the formula, X and Y represent a nitrogen atom or CH, and n represents an integer of any of 1 to 5. Xn and Y present in a total of 2n may be the same or different. R ^{1 to} R ⁸ each independently represent a hydrogen atom or a substituent, and two of R ^{1 to} R ⁸ bonded to adjacent carbon atoms are bonded to each other. And when n is 2 or more,
A plurality of R ^{1 to} R ⁸ may be the same or different. ) 2. The liquid crystal composition according to claim 1, wherein D ¹ and D ² are chromophores of an azo dye or an anthraquinone dye. 3. The liquid crystal composition according to claim 1, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2). Embedded image (Expressed in the formula, Ar ¹ to Ar ⁴ of the substituted or unsubstituted each independently is an aryl group or a heteroaryl group, L ¹
And L ² each independently represent a linking group, and n ¹ and n ²
Each independently represents 0 or 1, and Q represents a divalent group represented by the following formula (Q). ) (In the formula, X and Y represent a nitrogen atom or CH, and n represents an integer of any of 1 to 5. Xn and Y present in a total of 2n may be the same or different. R ^{1 to} R ⁸ each independently represent a hydrogen atom or a substituent, and two of R ^{1 to} R ⁸ bonded to adjacent carbon atoms are bonded to each other. And when n is 2 or more,
A plurality of R ^{1 to} R ⁸ may be the same or different. ) 4. The divalent group represented by Q includes any divalent group represented by the following general formulas (Q-1) to (Q-3). 4. The liquid crystal composition according to any one of items 1 to 3. Embedded image (Wherein, R ^{11 to} R ¹⁸ , R ^{21 to} R ²⁸ and R ^{31 to} R ³⁸ are
It represents a hydrogen atom or a substituent each independently, R ¹¹ ~
Two of R ¹⁸ , R ^{21 to} R ²⁸ and R ^{31 to} R ³⁸ which are bonded to adjacent carbon atoms may be bonded to each other to form a ring. ) 5. The divalent group represented by Q is any of the divalent groups represented by the general formulas (Q-1) to (Q-3). 4. The liquid crystal composition according to any one of items 1 to 3. 6. The compound represented by the general formula (1):
The liquid crystal composition according to claim 1, which is a compound represented by any one of the following general formulas (3) to (5). Embedded image (In the formula, Ar ^{1 to} Ar ⁴ each independently represent a substituted or unsubstituted aryl group or heteroaryl group.) 7. A liquid crystal device comprising a liquid crystal layer containing the liquid crystal composition according to claim 1. 8. An azo compound represented by the following general formula (6). Embedded image (Wherein, Ar ^{1 to} Ar ⁴ each independently represent a substituted or unsubstituted aryl group or heteroaryl group, L ¹ and L ² each independently represent a linking group, and n ¹ and n ² each represent Independently represents 0 or 1, and R ^{11 to} R ¹⁸ and R ²¹
To R ²⁸ each independently represent a hydrogen atom or a substituent,
Two of R ^{11 to} R ¹⁸ and R ^{21 to} R ²⁸ which are bonded to adjacent carbon atoms may be bonded to each other to form a ring. )