JPH0428788A - Liquid crystal composition and liquid crystal element - 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 [Field of Industrial Application] The present invention relates to a liquid crystal composition used in a liquid crystal element used in a display element or the like, and a liquid crystal element using the liquid crystal composition.

[Prior art and problems to be solved by the invention] Although liquid crystal elements have the remarkable feature of being able to operate with low power and low voltage, they are also easily activated by static electricity, etc., which makes it difficult to assemble the panel. Alternatively, it becomes an obstacle in the process of mounting the panel on a calculator, etc., and there is a problem in that it lowers the efficiency of final inspection and quality inspection in particular.

This problem can be solved by using a liquid crystal composition whose resistivity is controlled to about 109Ω·cam, but in order to obtain such a liquid crystal composition, it is necessary to
Conventionally, attempts have been made to add ionic substances such as quaternary ammonium salts to liquid crystal compositions that exhibit a resistivity higher than that of Cra. However, these materials have insufficient compatibility and solubility with non-ionic ordinary liquid crystal materials, and are easily adsorbed near the injection port of the liquid crystal cell, making it difficult to distribute them uniformly in the liquid crystal cell. It had some problems.

SUMMARY OF THE INVENTION An object of the present invention is to provide a liquid crystal element that is less susceptible to damage caused by static electricity, and a stable liquid crystal composition with low specific resistance for realizing this element.

[Means to solve the problem]

The present invention is based on the novel finding that although cryptands are nonionic substances, the addition of a small amount of cryptands significantly reduces the resistivity of a liquid crystal composition. and a liquid crystal element using the same. The present invention will be explained in detail below.

The resistivity of a liquid crystal composition, like other liquid substances, largely depends on its purity, but liquid crystal elements using liquid crystal compositions containing impurities often have problems with their lifespan, so they are usually There are sufficiently purified liquid crystal compositions available on the market, and such liquid crystal compositions are usually 1010
It has a specific resistance of ~1014Ω·Cl11. By adding cryptands at a low concentration to these liquid crystal compositions, the specific resistance can be lowered to a level of 10 9 Ω·cm.

The cryptands used in the present invention are expressed by the following formula (1
).

RI3 N -R14 (wherein R1 and R14 each independently represent a hydrogen atom, an alkyl group, an alkoxyalkyl group, an arylalkyl group, or an allyl group, and m and n each independently represent 0 or an integer of 1 to 5) represents.

Furthermore, R1 to R'R'-R" and R9 to RI2 may each form a ring, and RI3 and R14 may be bonded to each other to form -C2Ha (OC2Hn) I
(12 represents an integer of 1 to 5) may also be formed. ) Specific examples of these include 1,4.10trioxa-7,13-diazacyclopentadecane, 1,7,1
0.16-tetraoxa-413-diazacyclooctadecane, 4.13-didecyl-1,7,10,16-tetraoxer 4゜13-diazacyclooctadecane, 1
, 7.10° 13.19-pentaoxa-4,16-thiazacycloheneicosane, 4,7,13.18-tetraoxa-1,10-diazabicyclo(8,5,5)eicosane, 4,7. 13.16.21-pentaoxa-1
, 10-diazabicyclo(8,8,5)tricosane, 5
-Decyl-4,7,13,16゜21-pentaoxa-
1,10-diazabicyclo(8,8,5)) lycosane,
4,7,13,16゜21.24-hexaoxa-1,
10-diazabicyclo(8,8,8)hexacosane, 5
．． 6-benzo-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo(8,8,8)-
Hexacosane, 5.6-14.15-dibenzo-4,7
,13,16,21,24-hexaoxerl,10-
Diazabicyclo(8,8,8)hexacosane, 5-decyl-4,7,13,1621,24-hexaoxa-1
, 10-diazabicyclo-(8,8,8)-hexacosane and other cryptands.

Further, examples of the liquid crystal used in the present invention include various liquid crystal compounds shown by the following structural formulas and mixtures thereof.

(In the formula, RIS and R1- are each independently an alkyl group, an alkoxyalkyl group, an alkoxy group, an alkylphenyl group, an alkoxyalkylphenyl group, an alkoxyphenyl group, an alkylcyclohexyl group, an alkoxyalkylcyclohexyl group, and an alkylcyclohexylphenyl group. group, cyanophenyl group, cyano group, halogen atom, alkoxycarbonyl group, alkoxyalkoxycarbonyl group, alkylphenoxycarbonyl group, alkoxyalkylphenoxycarbonyl group, alkoxyphenoxycarbonyl group, alkylcyclohexyloxycarbonyl group, alkoxycyclohexyloxy carbonyl group, alkylcyclohexylphenoxycarbonyl group,
Cyanophenoxycarbonyl group, halogen phenoxycarbonyl group, alkylphenylalkyl group, alkoxyalkylphenylalkyl group, alkoxyphenylalkyl group, alkylcyclohexylalkyl group, alkoxyalkoxycyclohexylalkyl group, alkylcyclohexylphenylalkyl group, cyanophenylalkyl group and may have an optically active center in the alkyl chain or alkoxy chain. Furthermore, the phenyl group or phenoxy group in "RISR" may be substituted with a halogen atom such as a fluorine atom or a chlorine atom. Also, X and Y each represent a hydrogen atom or a halogen atom such as a fluorine atom or a chlorine atom. .

The cryptands used in the present invention can be added to the liquid crystal at a concentration within a range that does not significantly impair the transition point of the liquid crystal to an isotropic state and the stability of precipitation, separation, etc., but usually 0.
109Ω・CI with addition amount in the range of 3 to 3.0% by weight
The specific resistance can be reduced to 1 Lebel.

In the liquid crystal composition of the present invention, two or more different types of cryptan can be used in combination.

The liquid crystal composition of the present invention can be easily obtained by mixing cryptands and liquid crystal using a known method.

Further, optically active substances such as cholesteryl nonanoate, additives such as antioxidants, dichroic dyes commonly used in liquid crystal compositions, etc. may be used in combination.

The liquid crystal element of the present invention is a liquid crystal element constructed by sandwiching the above liquid crystal composition between the electrode-equipped substrates, at least one of which is transparent, and can be used in TN mode, guest-host mode, etc. Known field-effect mode and thermal writing mode liquid crystal elements [Mitsuharu Okano and Shunsuke Kobayashi [r-liquid crystal] application results, Baifukan, p. 13-p. 47;
J. L. Ferguson.

SID 85 Digest, p 68 (19
85) etc.].

Among these, preferred examples include field effect type liquid crystal elements such as TN mode and scattering control mode using easily charged substrates such as plastic films.

〔Effect of the invention〕

According to the present invention, a stable liquid crystal composition with a low specific resistance value can be obtained, and by using this composition, a liquid crystal element with few disturbances caused by static electricity can be constructed.

〔Example〕

EXAMPLES Hereinafter, the present invention will be explained in detail with reference to Examples, but the present invention is not limited by these Examples in any way.

Example 1 Cryptand (1°4.1
0-) Lyoxer 7.13-diazacyclopentadecane) Ig was dissolved in 100 g of a liquid crystal composition containing a phenylcyclohexane compound as a main component, which is commercially available under the trade name ZLI-1565 (E, manufactured by MERCK). A liquid crystal composition-① was prepared. This has a capacity of 1 ml and an electrode spacing of 1
．． 5 mm liquid electrode cell (manufactured by Ando Electric: LE-2
1), and measured the minute current value when a DC voltage of 10 V was applied using a high-sensitivity vibratory capacitance universal electrometer, and calculated the specific resistance value from the cell constant. In the case of only liquid crystal mixture ZLI-1565 5X10” (Ω・
CII+), whereas the liquid crystal composition -■ containing the cryptand of the present invention had a resistance of 6×10' (Ω·c+s).

After coating this liquid crystal composition -■ with polyimide resin and curing it,
Made of rubbed glass plate with transparent electrodes, 90°
The glass plates were sealed in a cell with a gap of 9 µm configured to have a twisted orientation, and the polarizing films were pasted together so that the rubbing direction of each glass plate and the transmission axis direction of the polarizing film matched, as shown in Figures 1 and 2. A TN type liquid crystal device shown in the figure was constructed. This liquid crystal element uses a square wave (5V, 64Hz
) was applied, and blinking was confirmed by turning the voltage ON and OFF.

Example 2 Cryptand (4゜13-
Didecyl-1,7,10,16-tetraoxa-4,1
3-Diazacyclooctadecane) 1g under the trade name ZLI-
1565 (E, manufactured by MERCK) and dissolved it in 200 g of a commercially available liquid crystal composition whose main component is a phenylcyclohexane compound to prepare a liquid crystal composition -1.

As a result of calculating the specific resistance value using the same measuring method as in Example 1, it was found that the liquid crystal composition containing the cryptand of the present invention
was 4×10′ (Ω·cm). This liquid crystal composition-
A liquid crystal device was produced in the same manner as in Example 1 using (2). When a rectangular wave (5 V, 64 Hz) was applied to this liquid crystal element, blinking was confirmed by turning the voltage ON and OFF.

Example 3 Cryptand (4°7.1
3.18-tetraoxa-1,10-diazabicyclo(
8,5,5) Eicosane) Ig under the trade name ZLI-156
Liquid crystal composition 1 whose main component is a phenylcyclohexane compound commercially available as 5 (manufactured by E1 MERCK)
00g to prepare a liquid crystal composition-■. As a result of calculating the specific resistance value using the same measuring method as in Example 1, it was found that the liquid crystal composition containing the cryptand of the present invention -■ was 9
This liquid crystal composition was X109(Ω・c+w)-■
A liquid crystal element was produced in the same manner as in Example 1 using the following. When a rectangular wave (5 V, 64 Hz) was applied to this liquid crystal element, blinking was confirmed by turning the voltage ON and OFF.

Example 4 Cryptand (4°7.1
3,16.21-pentaoxa-1,10-diazabicyclo(8,8,5)) lycosane) Ig under the trade name ZLI-
1565 (manufactured by E9MERCK) and dissolved in 100 g of a commercially available liquid crystal composition whose main component is a phenylcyclohexane compound to prepare a liquid crystal composition -1.

As a result of calculating the specific resistance value using the same measuring method as in Example 1, the liquid crystal composition containing the cryptand of the present invention -
■ was 6×10' (Ω·cm). Using this liquid crystal composition -1, a liquid crystal element was produced in the same manner as in Example 1. This liquid crystal element has a rectangular wave (5■.

When a voltage of 64 Hz) was applied, blinking was confirmed by turning the voltage ON and OFF.

Example 5 Cryptand (47,13
, 16,21,24-hexaoxa-1゜10-diazabicyclo(8,8,8)hexacosane) Ig is a commercially available phenylcyclohexane compound commercially available under the trade name ZLI-1565 (manufactured by E0MERCK). A liquid crystal composition (2) was prepared by dissolving it in 200 g of the liquid crystal composition. The specific resistance value was calculated using the same measuring method as in Example 1, and as a result, the liquid crystal composition V containing the cryptand of the present invention had a resistivity of 6×10′ (Ω·cm).

Using this liquid crystal composition -1, a liquid crystal element was produced in the same manner as in Example 1. This liquid crystal element has a rectangular wave (5V
, 64 Hz) was applied, and blinking was confirmed by turning the voltage ON and OFF.

[Brief explanation of the drawing]

FIG. 1 shows a schematic cross-sectional view of a TN type liquid crystal element according to the present invention in a state where no voltage is applied. DESCRIPTION OF SYMBOLS 1... Incident light, 2... Polarizing plate, 3... Transparent glass plate, 4... Transparent electrode, 5... Alignment film, 6... Liquid crystal composition. FIG. 2 shows a schematic cross-sectional view of a TN type liquid crystal element according to the present invention in a voltage applied state. DESCRIPTION OF SYMBOLS 1... Incident light, 2... Polarizing plate, 3... Transparent glass plate, 4... Transparent electrode, 5... Alignment film, 6... Liquid crystal composition.

Claims (2)

[Claims] (1) A liquid crystal composition containing at least one type of cryptand represented by the following general formula [I]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I] (In the formula, R^1 to R^1^4 each independently represent a hydrogen atom, an alkyl group, an alkoxyalkyl group, an arylalkyl group, or an allyl group, m and n each independently represent 0 or an integer of 1 to 5. Also, R^1 to R^4, R^5 to R^6 and R^9 to
R^1^2 may each form a ring, R^1^2
3 and R^1^4 are combined with each other to form -C_2H_4(
OC_2H_4)_l- (l represents an integer from 1 to 5)
A group represented by may be formed. ) (2) A liquid crystal element using the liquid crystal composition according to claim 1.