JPH0321693A - Liquid crystal composition and display element using the same composition - 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 r Industrial Application Field The present invention relates to a novel color liquid crystal composition with excellent light resistance and a liquid crystal display element using the composition.

1. Conventional technology] Display elements that utilize the guest-host effect by adding dichroic dyes to liquid crystals have 1) wide viewing angles, 2) a variety of display colors can be easily achieved by selecting the dyes, and 3) polarization. It is attracting attention as a display element particularly suitable for medium to large-sized displays because it does not necessarily require a plate and can provide a bright display.

[Problem to be solved by the invention]

However, conventional display elements that utilize the guest-host effect by adding dichroic dyes to liquid crystals have had difficulty simultaneously satisfying high contrast, long life, and a variety of hues. The reason for this is that there are few dichroic dyes with excellent both dichroism and photometry, and when different types of dyes are combined, photodegradation of one of the dyes, especially UV light, is often accelerated. The problem is that the light resistance is lower than when the dye is used alone. There is a problem in that the deterioration caused by light that occurs in this way is observed as discoloration or fading, and is measured as an increase in current consumption.

Therefore, for various hues that conventionally require the combination of yellow, red, and blue dichroic pigments such as black, brown, and dark blue, it is particularly important to achieve both contrast and long life. The problem was that it was difficult.

An object of the present invention is to provide a novel color liquid crystal composition that can solve the conventional problems as described above, and a liquid crystal display element using the composition.

(Means for Solving the Problems) As a result of intensive studies to achieve the above object, the present inventors have discovered a novel color liquid crystal composition that is excellent in both contrast and lifespan, and have arrived at the present invention. That is, The following general formula rI] (in the formula [■], R3 represents a hydrogen atom, an alkyl group, an alkoxyalkyl group, or an alkoxy group, and Y
represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxyalkyl group, or an alkoxy group, and X1 is the 〇1-position or m
It represents a phenylene group which may have a halogen atom, an alkyl group, or an alkoxy group substituent at the 1-position. ] A quinophthalone dichroic dye represented by the following general formula rll) where Rl is a hydrogen atom, a halogen atom, an alkyl group, an alkoxyalkyl group, an alkoxy group, an alkylphenyl group, an alkoxyphenyl group, or c the following general formula Substituent O OH represented by (1) (wherein R4 is a hydrogen atom, a halogen atom, an alkyl group,
It represents an alkoxyalkyl group, an alkoxy/group, or a cyclohexyl group which may have a substituent of an alkyl group, an alkoxyalkyl group, or an alkoxy group, and X2 is a hydrogen atom,...a rogen atom, an alkylcarboxylic acid ester group, an alkoxy an alkylcarboxylic acid ester group, or a phenylcarboxylic acid ester group having a phenyl group optionally substituted with a hano-rogen atom, an alkyl group, an alkoxyalkyl group or an alkoxy group, or an alkyl group;
Indicates a cyclohexylcarboxylic acid ester group including a cycloxyl group which may be substituted with an alkoxyalkyl group or an alkoxy group. ) An anthraquinone dichroic dye represented by the following general formula (IV) (wherein R5 is a hydrogen atom, an alkyl group, an alkoxyalkyl group, an alkoxy group, or a substituent of an alkyl group, an alkoxyalkyl group, or an alkoxy group) R6 represents a cyclohexyl group which may be substituted with a hydrogen atom, a rogen atom, anolequinole group, an alkoxyalkyl group, an alkoxy group, or an alkyl group, an alkyl group, or an alkoxy group. 7 represents a chlorohexyl group) and an anthraquinone dichroic dye represented by the following general formula 1'V] or an alkoxy group, and R8 is a hydrogen atom, an alkyl group, an anolecoquinalkyl group, or an alkyl group, an alkoxy7 alkyl group, or an alkoxy group having a substituent. Among the anthraquinone dichroic dyes represented by formula r
At least one type of quinophthalone dichroic dye represented by l), at least one type of anthraquinone dichroic dye represented by the general formula [■], anthraquinone dichroic dye represented by the general formula (lV'l) A liquid crystal composition comprising at least one dye, at least one anthraquinone dichroic dye represented by the general formula [■], and a liquid crystal substance; The gist is a liquid crystal display element supported between substrates.

To explain the present invention in more detail, R1 in the above general 2m includes a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom; a methyl group, an ethyl group, a proyl group, a butyl group, Pentyl group, hexyl group, octyl group,
Straight-chain or branched alkyl groups such as nonyl group and dodel/l group; straight-chain or branched alkyl groups such as methoxymethyl group, butoxymethyl group, methoxopyryl group, ethoxyethyl group, butoxyethyl group, etc. alkoxyalkyl group; methoxy group,
Straight or branched alkoxy groups such as ethoxy group, propoquine group, butoxo group, bentoxy group, octokizo group;
Straight chain or branched alkylphenyl groups such as ethylphenyl group, probylphenyl group, butylphenyl group, hexylphenyl group, nonylphenyl group; methoxyphenyl group, ethoxyphenyl group, phthoxyphenyl group, pentoxyphenyl group Examples of R2 in the general formula (1) include a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom; a methyl group; Straight-chain or branched alkyl groups such as ethyl group, proyl group, butyl group, pentyl group, hexyl group, octyl group, nonyl group, dodecyl group; methoxymethyl group, phthoxymethyl group, methoxybrobyl group, ethoxy Straight chain or branched alkoxyalkyl groups such as ethyl group, butoxyethyl group: Straight chain or branched alkoxy groups such as methoxy group, ethoxy group, bropoxo group, butoxy group, pentoxy group, octoxy group, etc. Examples of R3 in the general formula (1) include hydrogen atom;
Methyl group, ethyl group, proyl group, butyl group, pentyl group, hexyl group, octyl group, nonyl group, linear or branched alkyl group of dodecyl group; methoxymethyl group,
Linear or branched alkoxyalkyl groups such as butoxy/methyl group, methoxybrobyl group, ethoxyethyl group, butoxyethyl group; methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, octoxy group Examples include straight-chain or branched alkoxy groups such as
Substituents for the optionally substituted phenylene group of X1 in 1'l include halogen atoms such as fluorine atom, chlorine atom, and bromine atom; methyl group, ethyl group, proyl group,
Straight chain or branched alkyl groups such as butyl group and pentyl group; straight chain or branched alkoxy groups such as methoxy group, ethoxy group, propoxy group, putoxy group, and pentoxy group; As R4 in the general formula (■) and R6 in the general formula (IV) shown above, hydrogen atom; halogen atom such as fluorine atom, chlorine atom, bromine atom; methyl group, ethyl group, proyl group, butyl group, Straight chain or branched alkyl groups such as bentyl group, hexol group, octyl group, nonyl group, dodecyl group; Straight chain such as methoxymethyl group, butoxymethyl group, methoxypropyl group, ethoxyethyl group, butoxyethyl group Straight-chain or branched alkoxyalkyl group: Straight-chain or branched alkoxy group such as methoxy group, ethoxy group, propoxy group, putoxy group, pentoxy group, octoxy group; 7-chlorohexyl group, propyrunchlorohexyl group, butylcyclohexyl group, pentylcyclohexyl group, hexylcyclohexyl group, octylcyclohexyl group, methoxymethylcyclohexyl group, butoxyethyl/pentylcyclohexyl group, pentoxy7butylcyclohexyl group, methoxycyclohexyl group, bropoxinchlorohexyl group groups, linear or branched alkyl groups such as octoxycyclohexyl groups, alkoxoalkyl groups,
Indicates a cyclohexyl group which may be substituted with an alkoxy group, etc., and X2 in the general formula (ll[) shown above is a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom; a methyl group, an ethyl alkylcarphonic acid ester groups having linear or branched alkyl groups such as methoxymethyl, butyl, octyl, etc.; an alkoxyalkylcarboxylic acid ester group having a chain or branched alkoxyalkyl group;
Halogen atoms such as phenyl group, fluorophenyl group, chlorophenyl group, fromophenyl group, ethylphenyl group, phthylphenyl group, octylphenyl group, methkinmethylphenyl group, ptoxyethylphenyl group, phthoxyphenyl group, octyloxyphenyl group, Sulfenylcarboxylic acid ester group with a phenyl group optionally substituted with a linear or branched alkyl group, alkoxy/alkyl group, or alkoxy group; cyclohexyl group, proylcyclohexyl group, butylcyclohexyl group, pentylcyclohexyl group groups, hexylcyclohexyl group, octylcyclohexyl group, methoxymethylcyclohexyl group, butquinethylcyclohexyl group, pentoxy/butylcyclohexyl group, methoxy/butylcyclohexyl group, bropoxinchlorohexyl group, octoxycyclohexyl group, etc. R5 and The general formula shown above (
R7 in V) is a hydrogen atom; a linear or branched alkyl group such as a methyl group, an ethyl group, a probyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, a nonyl group, a dodecyl group, etc. ; Straight-chain or branched alkoxyalkyl groups such as methoxymethyl group, ptoxymethyl group, methoxypropyl group, ethoxyethyl group, butoxyethyl group; methoxy group, ethoxy group, globoxy group, putoxy group, pentoquine group, octoxy group Straight-chain or branched alkoxy groups such as cyclohexyl group, proylcyclohexyl group, butylcyclohexyl group, pentylcyclohexyl group, hek7lycyclohexyl group, octylcyclohexyl group, methoxymethylcyclohexyl group, phthoxy Straight-chain or branched alkyl groups, alkoxyalkyl groups, alkoxy groups such as ethylcyclohexyl group, bentoxybutylcyclohexyl group, methoxycyclo-quizol group, propoxycyclohexyl group, octoxycyclohexyl group Indicates a cyclohexyl group which may be substituted with, and R8 in the above general formula [V] is a hydrogen atom; methyl group, ethyl group, proyl group, butyl group, bentyl group, hexyl group, octyl group, nonyl group , straight-chain or branched alkyl groups such as dodecyl group; straight-chain or branched alkyl groups such as methoxy/methyl group, butoxy7-methyl group, methoxyglobyl group, ethoxy/ethyl group, and poxyethyl group (7) 7-rukoxyalkyl group; cyclohexyl/propylcyclohexyl group, butylcyclohexyl group, benzylcyclohexyl group, hekylenecyclohexyl group, octylzoclohexyl group, methoxymethylcyclohexyl group, butoxy/ethyl 7-hexyl group group, bentoxybutylcyclohexyl group, methoxycyclohexyl group, flopoxycyclohexyl group, octoxycyclohexyl group, straight chain or branched alkyl group, alkoxyalkyl group, alkoxy group, etc. Good cyclohexyl group;
Direct groups such as phenyl group, ethylphenyl group, butylphenyl group, octylphenyl group, methoxymethylphenyl group, phthoxyethylphenyl group, phthoxy/phenyl group, octyloxyphenyl group, fluorophenyl group, chlorophenyl group, promophenyl group, etc. Examples include chain or branched alkyl groups, alkoxyalkyl groups, alkoxy groups, and phenyl groups optionally substituted with halogen atoms.

More specifically, the general formula ('l) shown above, CI. ) is the structure of the quinophthane dichroic dye R2 R3 -C5H11(n)? C8H1■(n) {} {} -C5H,1(n) -C5H11(n) {} O -CH2-0-CH3 -H {t{} ? C5H,■(n)? C5H, ■(n) {} O etc., and the structure of the anthraquinone dichroic dye represented by the general formula (IV) shown above is the structure of a chromatic dye. As R5 -H {E)-0-C5H11(n) {n, H7(n) 80-C4H9(t) {}C2H4-O-C3H7(n) -C6H13(n) -C2H4-O-CH3 -O-C5H1, (n)? C8H,■(n) ACH2-0-C3H7(n) etc., and the like are mentioned, and as a liquid crystal material used in the present invention as the structure of the anthraquinone dichroic dye represented by the general formula rV) shown above, Is the following general formula R7 -C4H9(n) -H R8? 4H9(n) uC4H9(n) {$CH2
-0-C3H7(n) -H-C5H,■(n)
8CH2-0-C2H5-0-CH3uc2H5
-0-CH3 and the like.

(In the formula, R9, RIO is an alkyl group, an alkoxyalkyl group, an alkoxy group, an alkylphenyl group, an alkoxyalkylphenyl group, an alkoxyphenyl group, an alkylcyclohexyl group, an alkoxyalkylcyclohexyl group, an alkylcyclohexylphenyl group, a cyanophenyl group. , /ano group, halogen atom, alkoxycarbonyl group, alkoxyalkoxycarbonyl group, alkylphenoxycarbonyl group, alkoxyalkylphenoki7carbonyl group, alkoxyphenoxocarbonyl group,
Alkylcyclohexyl/ruoxycarbonyl group, alkylcyclohexyloxy/carponyl group, alkylcyclohexylphenox7carbonyl group, cyanophenoxycarbonyl group, halogenphenoxocarbonyl group, alkylphenylalkyl group, alkoxyalkylphenylalkyl group, alkoxyphenyl group It represents an alkyl group, an alkylcyclohexylalkyl group, an alkoxyalkoxycyclohexylalkyl group, an alkylcyclohexylphenylalkyl group, and a cyanophenylalkyl group, and may have an optically active center in the alkyl chain or alkoxy chain. Further, the phenyl group or fenoquine group in R9 and R10 may be substituted with a nitrogen atom such as a fluorine atom or a chlorine atom. Moreover, X3 is a hydrogen atom or a fluorine atom,
Indicates a halogen atom such as a chlorine atom. ) or a mixture thereof.

Further, the liquid crystal mixture may contain an optically active substance such as cholesteryl nonanoate, or an additive such as an ultraviolet absorber or an antioxidant.

The liquid crystal composition of the present invention has the general formula (1), 1"I)
, CIV) and [v] by dissolving at least one type of each of the dyes shown in [v] in the liquid crystal substance.

[Effect]

By supporting the liquid crystal composition prepared in this way between electrode substrates, at least one of which is transparent, a color liquid crystal display element with excellent light resistance applying the guest-host effect (Shoichi Matsumoto, Ichiyoshi Kakuda, “Latest technology of liquid crystal” 34-3
5 pages, published by Kogyo Kenkyukai (1983)
; J, L, Ferguson, SID 85 D
igest, p68 (1985), etc. ] can be configured.

(Example) Next, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to the following examples unless it exceeds the gist thereof.

In the following examples, the quality of dichroism is determined by the order parameter (S) of the dye compound obtained from the following formula.
Evaluated by.

Here, A and A↓ are the absorbances of the dye for light polarized parallel and perpendicular to the alignment direction of the liquid crystal, respectively. Specifically, the order parameter (8) is a value that indicates the display contrast of a guest-host type liquid crystal display element.Theoretically, as this value approaches 1, the degree of residual color in white areas decreases, making it brighter. Clear display with high contrast is possible.

1. Regarding the dyes of the present invention used in the following examples, their respective structural formulas with [厘] added are shown in Table 1 below.
I listed it as 1.

Table-1 (Part 2) Table-1 (Part 1) Table-1 (Part 3 Table-1 (Part 4) Table-1 (Part 5) Example 1 The dichroic dyes listed in Table-1 below were Product name ZL l-
Liquid crystal composition-1 was prepared by dissolving it in liquid crystal mixture 1007 mainly containing a phenyl-7-chlorohexane compound commercially available as 1565 (E, manufactured by MERCK).
adjusted.

Dye ['l-1) 0.65f (1-2) o. 7oy CI [-1) 1.88ノ (■-1) 0.95t (V-1) 0.85f (■-9) 0.75f This was coated with polyimide resin and cured, then rubbed and subjected to homogeneous alignment treatment. The gear 1 is made of a glass plate with transparent electrodes and is configured such that the orientation treated surfaces face each other.
A liquid crystal display element was produced by encapsulating it in a 9 μm cell.

The order parameter 6> of this liquid crystal display element was calculated and found to be 0.74, 0.73, and 0.73 at 574 nm, 539 nm, and 458 nm, respectively. A light resistance test was conducted on a cell containing Uniform Liquid Crystal Composition I using a fade meter (carbon arc light source). -7, and the change in absorbance of each absorption peak (574 nm, 539 nm, 458 nm) was 3% or less.

Example 2 The dichroic dye shown in Table 1 below was used under the trade name zLI-1.
A liquid crystal composition was prepared by dissolving it in a liquid crystal mixture 100f whose main component is a phenylcyclohexane compound commercially available as 565 (manufactured by E.MERC).

Dye (1-3) 0.95F (1-4') 0.85F (III-2) 1. asy (1-3) 1. x7y (TN-3) 1.20r (V-2') o. 3sy (:V-3':l o.44t rV-4) o. 6 sy ('i-9) 1. x4y [V-to) o. 6sy This is made of a glass plate with a transparent electrode that has been homogeneously aligned by applying and curing a polyimide resin and rubbing it, and the gear 1 is configured so that the alignment treated surfaces face each other.
A liquid crystal display element was produced by encapsulating it in a 9 μm cell.

As a result of calculating the order parameter 6) of this liquid crystal display element, 574 nm, 538 nm, and 460 nmK
k and were 0.74, 0.72 and 0.73, respectively. As a result of carrying out a light resistance test using a fade meter (carbon arc light source) on a cell filled with liquid crystal composition -■, the hue change after 200 hours: △E''(L"a"b
” method) must be 3.2 or less, and the increase rate of current value I/Io (
The applied voltage: 5v, 32Hz) was 2.7, and the absorbance change of each absorption peak (574nm, 538nm, and 46onm) was 3 or less.

Example 3 The black dichroic dye shown in Table 1 below was manufactured under the trade name ZL1-1.
A liquid crystal composition 1 was prepared by dissolving it in a liquid crystal mixture 1005' whose main component is a phenylcyclohexane compound commercially available as s6s (E, MERCK Co., Ltd.).

Dye ({ 5) 0.609 (1-6) 0.555' (1-7) 0.60r Nll-4) t. ttr (II-6) x. 4sr (■-21) 1.225+ (■-4) 1.14 g CV-5) 1. 3 5 1 [V-6]
x. 44t This is made of a glass plate with transparent electrodes that has been coated with polyimide resin and cured, then lapped and homogeneously aligned.
A liquid crystal display element was produced by encapsulating it in a 9 μm cell.

As a result of calculating the order parameter (S) of this liquid crystal display element, it was 0.73 and O,72 for 578 nm and 4 (i2 nm), respectively.Liquid crystal composition 1
As a result of carrying out a light resistance test using a fade meter (carbon arc light source), the cell encapsulated with . △E (L"a'b" method) is 3.7 or less, and the increase rate of current value is 1 / I o (applied voltage = 5■
, 3 2Hz) is &3, and each absorption peak (57
The absorbance change at 8 nm and 462 nm was less than 3.6 times.

Example 4 The dichroic dye shown in Table IA below was used under the trade name ZLl-1.
840 (manufactured by MERCK), a liquid crystal mixture mainly containing a phenyl hexane compound 100? A liquid crystal composition 1 was prepared by dissolving the liquid crystal composition.

Dye ({-1) 1.00f ()-4) 0.439 [1-1) 0.989 (1-5"l t2zy (#-2) 1.33F (V-7') 0.98? (vs] o.ss9 (V-11) o.63y rV-12) o.6sy (V-13) 0.77F After coating and curing polyimide resin, homogeneous alignment treatment was performed by rubbing/gating. A liquid crystal display element was prepared by sealing a glass plate with transparent electrodes in a cell with a gap of 9 μm, with the alignment-treated surfaces facing each other.

As a result of calculating the order parameter 6) of this liquid crystal display element, 577 nm, 541 nm, and 4 5 9 n
m K ,%- were 0.74, 0.73 and 0.73, respectively. As a result of carrying out a light resistance test using a fade meter (carbon arc light source) on a cell filled with liquid crystal composition 1, the hue change after 200 hours: ΔE
(L"a"b7 method) is 3.7 or less, the increase rate of current value 1/Io (applied voltage: 5V, 32Hz) is Z9, and each absorption peak (577nm., 541nm. and 4
The change in absorbance at 59 nm) was 3.5% or less.

Example 5 The dichroic dye shown in Table IA below was used under the trade name ZL +-
1 s 4 0 (E, MERCK Co., Ltd.) A liquid crystal composition -1 was prepared by dissolving it in a liquid crystal mixture 1001 whose main component is a phenylzochlorohexane compound commercially available from Toshite.

Dye CI-8) O, 409 [:l-9) 0.63f [1-10] o. z5y (#-2) o. ssf (1-3) 1.03f (il1-7] 0.639 CW-5) 1. zxy (■-6) 0.96f (V-10) 0.769 CV-14) 0.79F rV-1s:) o. qsr This is made of a glass plate with a transparent electrode that has been homogeneously aligned by applying and curing a polyimide resin and rubbing it, and the gear 1 is configured so that the alignment treated surfaces face each other.
A liquid crystal display element was produced by encapsulating it in a 9 μm cell.

As a result of calculating the order parameter ■ of this liquid crystal display element, 667 nm, 574 nm, 540 nm and 45 nm
At 2 nm, 0.74, 0.73, and 0.7, respectively.
3 and 0.72. As a result of carrying out a light resistance test using a fade meter (carbon arc light source) on a cell filled with liquid crystal composition -■, the hue change after 200 hours was as follows:
ΔE"(L'a'b" method) is 3.5 or less, the increase rate of current value is 1/I0 (applied voltage: sV, 3zHz)
is 8, and each absorption peak (667 nm, s 7
The absorbance change at 4 nm, 540 nm, and 452 nm was 4% or less.

〔Effect of the invention〕

As is clear from the above results, the color liquid crystal composition containing the specific combination of dichroic dyes of the present invention and the liquid crystal display element using the liquid crystal composition have the guest host effect of adding dichroic dyes. Conventionally, it has been used for various hues such as black, brown, and dark flange, which have excellent light resistance and require the combination of dichroic pigments such as yellow, red, and blue. My sister is in trouble. It has a remarkable effect of industrial value, making it possible to achieve both the contrast and long life that were thought to be possible.

Claims (2)

[Claims] (1) The following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・[I
[In the formula, R^1 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxyalkyl group, an alkoxy group, an alkylphenyl group, an alkoxyphenyl group, or a substituent represented by the following general formula [II] ▲ Numerical formula, chemical formula, table etc. ▼・・・・・・[II] (In formula [II], R^3 represents a hydrogen atom, an alkyl group, an alkoxyalkyl group, or an alkoxy group, and Y is ▲ Formula,
There are chemical formulas, tables, etc. ▼ groups or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Indicates groups. ), R^2 is a hydrogen atom,
It represents a halogen atom, an alkyl group, an alkoxyalkyl group, or an alkoxy group, and X^1 represents a phenylene group which may have a halogen atom, alkyl group, or alkoxy group substituent at the o-position or m-position. ] Quinophthalone dichroic dye, the following general formula [III] ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・[III
] (wherein R^4 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxyalkyl group, an alkoxy group, or a cyclohexyl group which may have a substituent of an alkyl group, an alkoxyalkyl group, or an alkoxy group, X^2
is a hydrogen atom, a halogen atom, an alkylcarboxylic acid ester group, an alkoxyalkylcarboxylic acid ester group, or a phenylcarboxylic acid ester group having a phenyl group optionally substituted with a halogen atom, an alkyl group, an alkoxyalkyl group, or an alkoxy group, or an alkyl group,
Indicates a cyclohexylcarboxylic acid ester group having a cyclohexyl group which may be substituted with an alkoxyalkyl group or an alkoxy group. ) Anthraquinone dichroic dye represented by the following general formula [IV] ▲ Numerical formulas, chemical formulas, tables, etc. are available▼・・・・・・[IV] (In the formula, R^5 is a hydrogen atom or an alkyl group , represents an alkoxyalkyl group, an alkoxy group, or an alkyl group, an alkoxyalkyl group, or a cyclohexyl group which may have an alkoxy substituent, and R^6 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxyalkyl group, Anthraquinone dichroic dye represented by an alkoxy group, or a cyclohexyl group optionally substituted with an alkyl group, an alkoxyalkyl group, or an alkoxy group, and the following general formula [V] ▲Mathematical formula, chemical formula, table, etc. There is R^8 represents a cyclohexyl group which may have a hydrogen atom, an alkyl group, an alkoxyalkyl group, or a cyclohexyl group which may have a substituent of an alkyl group, an alkoxyalkyl group or an alkoxy group, or an alkyl group, an alkoxy Among the anthraquinone dichroic dyes represented by the general formula [
At least one quinophthalone dichroic dye represented by [I], at least one anthraquinone dichroic dye represented by general formula [III], and anthraquinone dichroic dye represented by general formula [IV] A liquid crystal composition comprising at least one of the following, at least one anthraquinone dichroic dye represented by the general formula [V], and a liquid crystal substance. (2) A liquid crystal display element, characterized in that a liquid crystal composition is supported between electrode substrates, at least one of which is transparent, and the composition according to claim 1 is used as the liquid crystal composition.