JPH0674425B2 - Liquid crystal composition and display device - Google Patents

Description

TECHNICAL FIELD The present invention relates to a color liquid crystal composition having excellent light resistance and a display device.

(Prior Art) A display device utilizing the guest-host effect in which a dichroic dye is added to liquid crystal has 1) a wide viewing angle, 2) various display colors can be easily realized by selecting a dye, and 3) polarized light Since it does not necessarily require a plate, bright display is possible, and so on, it is attracting attention as a display element particularly suitable for medium to large display.

(Problems to be Solved by the Invention) However, conventionally, it is difficult for a display device using a guest-host effect by adding a dichroic dye to liquid crystal, to simultaneously satisfy high contrast, long life and various hues. Met. This is due to the fact that there are few dichroic dyes that have both excellent dichroism and light resistance, and when different types of dyes are blended, photodegradation of one of the dyes, especially deterioration by ultraviolet light, is often accelerated. The light resistance is lower than that when the dye is used alone. The deterioration due to the light thus generated is observed as discoloration or fading, and there is a problem that it is measured as an increase in current consumption. Therefore, also conventionally, for example, black, brown,
The problem that it is difficult to achieve both contrast and long life for a wide variety of hues such as dark blue that requires the addition of three types of dichroic dyes of yellow, red and blue. was there.

An object of the present invention is to provide a color liquid crystal composition and a display device capable of solving the above conventional problems.

(Means for Solving the Problems) As a result of intensive studies to achieve the above object, the present inventors have found a liquid crystal composition having both excellent contrast and life, and completed the present invention. That is, the present invention has the general formula [I] (In the formula, R ¹ and R ² represent a hydrogen atom, an alkyl group, an alkoxyalkyl group or an alkoxy group.) And a general formula [II] (In the formula, R ³ represents a hydrogen atom, an alkyl group, an alkoxyalkyl group or an alkoxy group, and X represents a hydrogen atom, a halogen atom or a carboxylic acid ester group.) And a general formula [ III) (In the formula, R ⁴ represents an alkyl group, an alkoxyalkyl group or an alkoxy group, and R ⁵ represents a hydrogen atom, an alkyl group, an alkoxyalkyl group or an aryl group.) At least one dichroic dye A gist of the present invention is a liquid crystal composition containing the same, and a liquid crystal display device in which at least one of the liquid crystal compositions is carried between transparent electrode substrates.

To explain the present invention in more detail, the general formula [I] shown above,
As R ^{1 to} R ⁴ in [II] and [III], a hydrogen atom,
A methyl group, an ethyl group, a linear or branched propyl group,
Alkyl groups such as butyl group, pentyl group, hexyl group, octyl group, nonyl group, dodecyl group; alkoxy such as methoxy group, ethoxy group, linear or branched propoxy group, butoxy group, pentoxy group, octoxy group, etc. Groups. X in the general formula [II] shown above is a hydrogen atom; a halogen atom such as a chlorine atom or a bromine atom; a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, an octoxycarbonyl group, a butylphenoxycarbonyl group, an octyl group. Examples of the carboxylic acid ester group such as enoxycarbonyl group, butoxyphenoxycarbonyl group, trans-4-butylcyclohexyloxycarbonyl group, trans-4-octylcyclohexyloxycarbonyl group, R in the general formula [III] shown above.
⁵ is an alkyl group such as hydrogen atom, methyl group, ethyl group, linear or branched propyl group, butyl group, pentyl group, hexyl group, octyl group, nonyl group, dodecyl group; methoxyethyl group, butoxy group Examples thereof include alkoxyalkyl groups such as ethyl group, methoxypropyl group and butoxypropyl group; aryl groups such as phenyl group, butylphenyl group, octylphenyl group, butoxyphenyl group and octyloxyphenyl group.

The liquid crystal substance used in the present invention has the following general formula: (In the formula, R ⁶ and R ⁷ are an alkyl group, an alkoxyalkyl group,
Alkoxy group, alkylphenyl group, alkoxyalkylphenyl group, alkoxyphenyl group, alkylcyclohexyl group, alkoxyalkylcyclohexyl group, alkylcyclohexylphenyl group, cyanophenyl group,
Cyano group, halogen atom, alkoxycarbonyl group, alkoxyalkoxycarbonyl group, alkylphenoxycarbonyl group, alkoxyalkylphenoxycarbonyl group, alkoxyphenoxycarbonyl group, alkylcyclohexyloxycarbonyl group, alkylcyclohexyloxycarbonyl group, alkyl Cyclohexylphenoxycarbonyl group, cyanophenoxycarbonyl group,
Halogenophenoxycarbonyl group, alkylphenylalkyl group, alkoxyalkylphenylalkyl group, alkoxyphenylalkyl group, alkylcyclohexylalkyl group, alkoxyalkoxycyclohexylalkyl group, alkylcyclohexylphenylalkyl group,
It represents a cyanophenylalkyl group, and may have an optically active center in the alkyl chain or the alkoxy chain. ) A liquid crystal substance such as a simple substance of the compound represented by the formula) 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 and an antioxidant.

The liquid crystal composition of the present invention can be easily prepared by dissolving at least one of the dyes represented by the general formulas [I], [II] and [III] shown above in the liquid crystal substance.

(Function) By supporting the liquid crystal composition thus prepared between the electrode substrates, at least one of which is transparent, a color liquid crystal display device having an excellent light resistance to which the guest-host effect is applied [Shouichi Matsumoto, Kakuda] Ichiyoshi, "Latest LCD Technologies," pages 34-35, published by the Industrial Research Board (1983); JLFergason, SID85 Di
gest, P68 (1985), etc. ] Can be configured.

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

Example 1 The following structural formula [IV] 0.38 g of the dye represented by and the following structural formula [V] 0.28 g of the dye represented by and the following structural color [VI] 0.14 g of a dye represented by the following structural formula [VII] In the liquid crystal composition of the present invention by blending and dissolving 0.21 g of the dye shown in 10 g of a liquid crystal mixture containing a phenylcyclohexane compound commercially available under the trade name ZLI-1840 (manufactured by E. Merck) as a main component. Was prepared.

This was made of a glass plate with a transparent electrode treated with polyimide, and was enclosed in a cell with a gap of 9 μm configured so that the transparent electrodes face each other, and a light resistance test was performed with a fade meter (carbon arc light source). As a result,
Hue change after 300 hours: ΔE (L ^* a ^* b ^* method) is 1 or less, and each absorption peak (467 nm, 538 nm, 579 nm, 640 n)
The rate of change in absorbance of m) was 2% or less. It should be noted that, as compared with the composition prepared by removing the dye represented by [IV] from the composition, the composition exhibited a smaller change in hue and a change in absorbance, and exhibited excellent light resistance.

Example 2 Structural formula [VIII] below 0.32 g of the dye represented by and the following structural formula [IX] 0.21 g of the dye represented by the following structural formula [X] 0.31 g of the dye represented by the following, in a liquid crystal mixture 10 g containing a phenylcyclohexane compound commercially available under the trade name ZLI-1840 (manufactured by E. Merck) as a main component, compounded and dissolved to obtain a liquid crystal composition of the present invention. Was prepared.

Using this composition as a sample, a light fastness test was conducted in the same manner as in Example 1, and as a result, the absorption peak after 300 hours (468 nm, 530 nm, 6
The rate of change in absorbance at 60 nm) was 2% or less.

Example 3 0.04 g of the dye represented by the structural formula [IV], 0.18 g of the dye represented by the structural formula [V], 0.12 g of the dye represented by the structural formula [VI] and the structural formula [VII] Pigment
0.19 g was mixed and dissolved in 10 g of a liquid crystal mixture containing a phenylcyclohexane compound as a main component, which is commercially available under the trade name ZLI-1565 (manufactured by E. Merck) to prepare a liquid crystal composition of the present invention.

Using this composition as a sample, a light resistance test was conducted in the same manner as in Example 1. As a result, the absorbance at each absorption peak was higher than that of the composition prepared by removing the dye represented by the structural formula [IV] from the composition. Change rate of 2% or less and hue change: ΔE (L ^* a
^{When the *} b ^* method) was 3 or less, both were small and showed excellent light resistance.

Example 4 Instead of the dye represented by the structural formula [IX] in Example 2, the following structural formula [IX '] A liquid crystal composition of the present invention was prepared in the same manner as in Example 2 except that 0.2 g of the dye shown in was used, and a light fastness test was conducted in the same manner as in Example 1. As a result, the change in absorbance at each absorption peak was observed. The rate was 2% or less.

(Effects of the Invention) As is clear from the above results, the color liquid crystal composition containing the combination of the specific dichroic dyes of the present invention and the liquid crystal display device using the liquid crystal composition are added with the dichroic dyes. A variety of hues such as black, brown, and dark blue that utilize the guest-host effect and have excellent light resistance, and in particular require blending of three types of dichroic dyes of yellow type, red type and blue type. With respect to the above, it is possible to achieve both the contrast and the long service life, which have been difficult to achieve in the past, with the industrially significant effect.

Claims (2)

[Claims] 1. A general formula [I] (In the formula, R ¹ and R ² represent a hydrogen atom, an alkyl group, an alkoxyalkyl group or an alkoxy group.) And a general formula [II] (In the formula, R ³ represents a hydrogen atom, an alkyl group, an alkoxyalkyl group or an alkoxy group, and X represents a hydrogen atom, a halogen atom or a carboxylic acid ester group.) And a general formula [ III) (In the formula, R ⁴ represents an alkyl group, an alkoxyalkyl group or an alkoxy group, and R ⁵ represents a hydrogen atom, an alkyl group, an alkoxyalkyl group or an aryl group.) At least one dichroic dye A liquid crystal composition comprising: 2. A liquid crystal display device comprising a liquid crystal composition carried between electrode substrates, at least one of which is transparent, characterized in that the liquid crystal composition according to claim 1 is used as the liquid crystal composition. Liquid crystal display device.