JPS63205639A - Liquid crystal display element - Google Patents

Abstract

PURPOSE:To improve orientability and moisture resistance by incorporating an arom. polyether amide sulfone polymer having a specific repeating unit into a titled element. CONSTITUTION:This element contains the arom. polyether amide sulfone polymer having the repeating unit expressed by the formula I. In the formula, R1-R4 respectively independently denote hydrogen, lower alkyl group, lower alkoxy group or halogen, Ar denotes a p-phenylene group, m-phenylene group, diphenylene group, naphthylene group, etc. The arom. polyether amide sulfone polymer is insoluble in liquid crystals and water. An orientation control film is obtd. by dissolving this polymer in a specific solvent, coating the soln. prepd. on a substrate having a transparent conductive film consisting of indium oxide, etc., and drying the coating under heating, then rubbing the film. Two sheets of the substrates having such orientation control films are disposed in parallel to face each other and the liquid crystal is sealed therebetween. The orientability and moisture resistance of the liquid crystal are thereby improved.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a liquid crystal display element using a specific alignment control film.

(Prior Art) Parallel alignment processing methods for liquid crystal displays include methods of obliquely depositing oxides such as 8i0 on the substrate surface, and silane-based methods.

Apply a solution of titanium-based coupling agent, carbon, polyvinyl alcohol, fluororesin, silicone resin, polyamide, polyamideimide, polyimide, etc. to the substrate surface K.
ll! Remove the solvent (or harden reaction) by heating and drying, rubbing (rubbing in a certain direction with a cloth, etc.)
Methods have been proposed and put into practical use, but none of them have had sufficient characteristics. Recently, methods using plasma polymerized films, Leon beams, and plasma etching have been proposed, but these are not practical.

(Problems to be Solved by the Invention) The conventional alignment treatment method of obliquely vapor depositing an oxide such as 8i0 is not reliable when used as a device.

Although it has excellent durability, it requires patch processing, requires 9 hours of equipment, and increases manufacturing costs, making it impractical. Furthermore, this method is not suitable for the recent trends of increasing size and color. In addition, since the polyvinyl alcohol formulation that has been put into practical use in some areas is water-soluble, it is possible to print patterns such as off-cut and 7-lex on the substrate surface, and although it is excellent in workability, it is not suitable for devices. There are problems in that the moisture resistance reliability is poor (especially for plastic substrates) and the refractive index of the film is low, so the pattern of the transparent electrode can be seen even when the light is not lit (visibility).

Furthermore, the polyimide alignment agents commonly used at present are of excessive quality in terms of heat resistance and have a slight yellowish-brown color, which deteriorates the quality of one display.

Furthermore, since heat treatment is performed at 300° C. or higher for 30 minutes or more to complete the condensation of the imide rings, plastic cannot be used as the substrate material, and discoloration will occur if a color filter is incorporated. Furthermore, since high-temperature processing is performed, there are various process problems such as warping of the substrate and deformation of the rack. Furthermore, Japanese Patent Application Laid-Open No. 55-9518 discloses a liquid crystal display panel using a polymeric material (such as nylon) having an amide bond as an alignment treatment film, but this method requires the preparation of a solution of the alignment control film material.

The work must be carried out at extremely high temperatures, which is not always satisfactory.

Further, JP-A-58-37621 discloses a liquid crystal display element using aromatic polyetheramide as an alignment treatment film, but this method is not suitable.

Although it has excellent workability, the heat resistance of the resin is low.

Also, due to poor adhesion to the substrate, there are problems with reliability and the results are not necessarily satisfactory.

Therefore, the present invention solves the above-mentioned problems, enables pattern printing such as offset and flexography, and prints at 200°C.
The purpose of this invention is to provide a liquid crystal display element having an alignment control film that can be formed even at low temperatures below and has heat resistance.

(Means for Solving the Problems) The present invention provides that the alignment control film of a liquid crystal display element has the general formula (): % formula % () [where Rt, &s Rs and R4 each independently represent hydrogen or lower alkyl. group, lower alkoxy group or halogen, and Ar represents a p-phenylene group, a diphenylene group, a naphthylene group, or CHx or -CHx-. The present invention relates to a liquid crystal display element containing an etheramide sulfone polymer.

The aromatic polyetheramide sulfone polymer mentioned above is insoluble in liquid crystal and water, and this polymer is
An alignment control film is obtained by dissolving the solution in a certain solvent, coating it on a substrate having a transparent conductive film such as indium oxide, heating and drying it, and then rubbing it.

A relatively low heating temperature of 100 to 200°C is sufficient. A substrate 2 having an alignment control film prepared by K as described above.
By arranging the sheets parallel to each other and sealing the liquid crystal between them, a liquid crystal display element having satisfactory characteristics can be completed.

The liquid crystal display element of the present invention generally has good liquid crystal orientation and good moisture resistance. Therefore, substrate materials include glass, metal plates such as silicon, aluminum, and nickel, and epoxy acrylate resin.

A film or sheet made of polyethylene terephthalate or the like with a transparent conductive film can be used.In addition to this, a film or sheet with a liquid crystal insoluble film or a film or sheet whose surface has been treated so that it will not be dissolved by the liquid crystal It is applicable to any type of material (having a film), and is not particularly limited. Therefore, any conventionally known material may be used.

In the present invention, after applying a specific aromatic polyetheramide sulfone polymer solution to the substrate.

Since it is sufficient to simply evaporate and dry the solvent, an alignment control film can be obtained at low temperature and in a short time. For example, the film thickness to be formed is 200-30000A, preferably 500-20A
Since it is very thin with approximately 0OA, it can be sufficiently dried even at temperatures below the boiling point. Therefore.

Compared to the conventional method of obliquely depositing a thin film made of KS ioz or the like on a conventional substrate (mainly a glass plate) or the method of forming a polyimide film, it is possible to obtain an inexpensive liquid crystal display element very easily.

The aromatic polyetheramide sulfone polymer used in the present invention can be produced, for example, as follows.

Aromatic diamine represented by general formula (If) (wherein R1, R,, R3 and R4 are the same as above) and general formula a) XO
C-Ar-COX...""Ql
l) (where Artip-phenylene group is 9m-phenylene and xti represents chlorine or bromine), aromatic dicarboxylic acid cybalide can be prepared by known methods 9, such as solution polymerization method or as shown in JP-A-52-23198. It is obtained by reacting according to the method described above.

As the aromatic diamine represented by general formula (n).

Bis(4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, bis[3-methyl-4-(4-aminophenoxy)phenyl]sulfone.

Bis[3-chloro-4-(4-aminophenoxy)phenyl]sulfone, bis(3-promo 4-(4-aminophenoxy)phenyl)sulfone.

Bis[3-ethyl-4-(4-aminophenoxy)phenyl]sulfone, bis(3-7'ropyru-4-(4-aminophenoxy)phenyl)sulfone.

Bis[3-isopropyl-4-(4-aminophenoxy)phenyl]sulfone, bis[3-butyl-4-(4-
7minophenoxy)phenyl]sulfone, bis(3-5
ec-Butyl-4-(4-aminophenoxy)phenyl]sulfone, bis(3-methoxy-4-(4-aminophenoxy)phenyl)sulfone, bis[3-ethoxy-
4-(4-aminophenoxy)phenyl]sulfone, bis[3,5-dimethyl-4-(4-aminophenoxy)
phenyl]sulfone, bis(&5-dichloro4-(4
-aminophenoxy)phenyl]sulfone.

Bis(3,5-dibromo-4-(4-aminophenoxy)phenyl)sulfone, bis[λ5-dimethoxy4-
(4-aminophenoxy)phenyl]sulfone, bis[
3-chloro-4-(4-aminophenoxy)-5-methylphenyl]sulfone.

Bis[3-methyl-4-(3-aminophenoxy)phenyl]sulfone, bis[3-chloro-4-(3-aminophenoxy)phenyl]sulfone.

Bis[3-promo4-(3-aminophenoxy)phenyl]sulfone, bis[3-ethyl-4-(3-aminophenoxy)phenyl]sulfone.

Bis[3-propyl-4-(3-aminophenoxy)phenyl]sulfone, bis[3-isopropyl-4-(3
-aminophenoxy)phenyl]sulfone, bis[3-
Butyl-4-(3-aminophenoxy)phenyl]sulfone, bis(3-5ee-butyl-4-(3-aminophenoxy)phenyl)sulfone, bis[3-methoxy-
4-(3-aminophenoxy)phenyl]sulfone, bis[3-ethoxy-4-(3-aminophenoxy)phenyl]sulfone, bis(3,5-dimethyl-4-(3-
Aminophenoxy)phenyl]sulfone.

Bis[3,5-dichloro-4-(3-aminophenoxy)phenyl]sulfone, bis[3,5-dibromo-4-
(3-aminophenoxy)phenyl]sulfone, bis[
[lambda]5-dimethoxy4-(3-aminophenoxy)phenyl]sulfone, bis[3-chloro-4-('3-aminophenoxy)-5-methylphenyl]sulfo/natoka.

As the aromatic dicarboxylic acid cybaride represented by the general formula (ll[3) used in the present invention, all known aromatic dicarboxylic acid cybarides belonging to this are useful. For example, terephthalic acid dichloride, terephthalic acid dibromide.

Isophthalic acid dichloride, inophthalic acid diproma ()
', 4.4'-diphenyl ether dicarboxylic acid dichloride, 44'-diphenyl ether dicarboxylic acid dibromide, 4.4'-diphenylsulfone dicarboxylic acid dichloride Q4+'-diphenyl sulfone dicarboxylic acid dibromide, 44'-diphenyl dicarboxylic acid dichloride, 44 Examples include '-di7-dicarboxylic acid bromide, L5-naphthalene dicarboxylic acid dichloride, and 1,5-naphthalene dicarboxylic acid dichloride, and at least one of them is used.

The orientation ratio of the aromatic diamine and the aromatic dicarboxylic acid civalide is preferably 1 equivalent of the former to 0.9 equivalent of the latter.
~ L2 equivalent. If it is outside the above range, a product with a high molecular weight will be obtained.

There is a tendency that only oligomer-like products that do not exhibit resin-like properties are obtained. Particularly preferably, the latter aromatic dicarboxylic acid halide is in a range of 0.97 to 1.03 equivalents per equivalent of the former aromatic diamine. In particular, when the amounts are equal, the maximum molecular weight of the target aromatic polyamide sulfone resin can be obtained.

A portion of the aromatic diamine can be replaced by other known aromatic diamines up to 85 mol. From the viewpoint of solvent resistance and coloring properties, the amount should preferably be 50%, particularly preferably 30% (based on the total amount of aromatic diamine). Examples of other aromatic diamines include tbm-phenylenediamine, p
-phenylenediamine, 4.4'-diaminodiphenylmethane, 44'-diaminodiphenyl ether, 44'
-Diaminodiphenylsulfone #212- (4,
4'-diaminodiphenyl)furopane, 44'-diaminodiphenylsulfide, 1,5-diaminonaphthalene, 4,4'-diaminodiphenylethane, m-)luenediamine, 1)-)luenediamine, 3.4'-diaminobenzanilide e L4-diaminonaphthalene, 3'-cyclo44'-diaminodiphenyl, pentidine, 4.4'-diaminodiphenylamine, 4.4'
-diaminodiphenyl-N-methylamine, 44'-diaminodiphenyl-N-phenylamine, tome 3'-diaminodiphenylsulfone, 44'-diamino, diphenyldiethylsilane, 44'-diaminodiphenylsilane, 2,2-bis( Examples include 4-(4-aminophenoxy)phenyl]propane, and at least one of these is used.

Additionally, known aliphatic diamines such as piperazine,
Hexamethylene diamine, heptamethylene diamine, octamethylene diamine, nonamethylene diamine, decamethylene diamine, p-xylylene diamine, m-xylylene diamine, tetramethylene diamine, dodecamethylene diamine.

4.4'-dimethylhbutamethylenediamine, 3-methylhbutamethylenediamine, 2. Ll-cyamidodecal, 1.1.2-diaminooctadecane, etc. can also be used in combination with the above aromatic diamine. Furthermore, in order to improve the adhesion to the base material, known diamines having silicon groups introduced therein, for example, can be used.

3-bis(aminopropyl)tetramethyldisiloxane, 1.3-bis(aminopropyl)tetraphenyldisiloxane, 1.3-bis(aminopropyl)hexamethyltrisiloxane, etc. may be used in combination with the above aromatic diamine. can. However, as the amount of K added is increased, the heat resistance gradually decreases, so the amount of K added should be determined so as not to impair the purpose of the present invention, preferably 30 molti or less, 4! Preferably 10 molt or less (
Based on total diamine amount. ) are used together within the range.

When the aforementioned various diamines are used in combination, the blending ratio of all the diamine components and the aromatic dicarboxylic acid cybaride can be set on exactly the same basis as described above.

In the present invention, for the 9 reaction, a known method used for the reaction between an amine and an acid can be used as is, and the conditions are not particularly limited. For example, interfacial polycondensation method.

This can be achieved by a solution polycondensation method, a solution-polycondensation method, or the like. In the interfacial polycondensation reaction, a known water-soluble neutralizing agent described below is used. Also, triethylamine and pyridine in the case of solution polymerization method.

A known neutralizing agent consisting of a tertiary amine such as tributylamine is used. A reaction solvent is used in the interfacial polycondensation method and the solution polymerization method, but this solvent must be capable of dissolving at least one of aromatic diamine or aromatic dicarboxylic acid civalide, preferably both. . A representative example of a particularly effective reaction solvent used in the interfacial polycondensation process is cyclohexanone. Some examples of other solvents that can be used include methylene chloride, trichlene, and percrene.

Ethane dichloride, nitrobenzene, chloroform.

Carbon tetrachloride, diisobutyl ketone, acetophenone, p
-Methylacetophenone, etc.

The reaction solvent used in the solution polymerization method is N, N-
Dimethylformamide, N,N-dimethylacetamide, N,N-diethylformamide, N,N-diethylacetamide, N,N-dimethylmethoxyacetamide, dimethylsulfoxide, N-methyl-2-pyrrolidone, pyridine, dimethylsulfone, hexamethyl Phosphoramide, tetramethylene sulfone, dimethyltetramethylene sulfone.

1,3-dimethylimidazolidinone and the like are preferred.

Two or more reaction solvents may be used in combination, if necessary, to facilitate the dissolution operation. Further, in order to obtain a product with as high a molecular weight as possible, it is preferable to use a highly dehydrated solvent for dissolving the aromatic dicarboxylic acid cybalide. In particular, N,N-dimethylformamide, N,
When carrying out solution polycondensation using a polar solvent such as N-dimethylacetamide or N-methyl-2-pyrrolidone, 2 to 10% by weight of lithium chloride or calcium chloride is used as a co-solvent.

Synthesis by adding rhodan calcium or the like is advantageous because the solubility increases significantly.

The aromatic polyetheramide sulfone polymer of the present invention is
It is preferable that the reduced viscosity of a 0.2% dimethylformamide solution at 30° C. is 0.3 to λOd//g.

If this reduced viscosity is too small.

Solvent resistance decreases, and if it is too large, solubility in polar solvents tends to decrease.

Examples of solvents in which the aromatic polyetheramide sulfone polymer is dissolved during the preparation of the alignment control film include dimethyl sulfoxide, dimethyl formamide, dimethyl acetamide,
A solvent such as N-methyl-2-pyrrone, dimethylimidazolidinone, cyclohexanone, etc. alone or a mixture thereof, and a mixture thereof to the extent that the aromatic polyetheramide sulfone polymer can be dissolved may be used. can.

For example, rather than using the above solvents alone, cellosolves,
A mixed solvent containing appropriate amounts of toluene, xylene, etc. may yield a better film, and any solvent other than the above may be used without particular limitation as long as it can dissolve the aromatic polyetheramide sulfone polymer. 9 In the present invention, K is used to improve film formability and the like.

Other polymers may also be present.

(Example) Next, the present invention will be explained based on examples.

The present invention is not limited to these in any way.

The orientation of the liquid crystal display element was evaluated based on the angle formed between the long axis direction of the liquid crystal molecules and the surface of the substrate, that is, the inclination (tilt angle θ) K between the substrate and the long axis of the liquid crystal molecules. For good orientation, a tilt angle of approximately 1.0 to 10 is desirable, which not only increases the absolute value of the contrast ratio but also reduces defects such as reverse twist. [For details on tilt angle and its measurement method, please refer to the Journal Op.
Applied Physics (Journal of A
ppliedPhysics) *Volume 19 (1980)
, Nlll0. 2013-4].

Example 1 1 of an acid chloride mixture consisting of 50% by weight of terephthalic acid dichloride and 50% by weight of isophthalic acid dichloride
0wt% cyclohexanone solution (4-(4-
7minophenoxy)phenyl]sulfone 95% by weight and 1
．． A 20% by weight cyclohexanone solution of a diamine mixture consisting of 5% by weight of 3-bis(acinopropyl)tetramethylenedisiloxane was prepared in an amount of 10% in the presence of an aqueous sodium hydroxide solution in such a proportion that the acid chloride and diamine were equimolar. to react the acid chloride and diamine,
The resulting aromatic polyetheramide sulfone polymer was isolated. This was dissolved again in dimethylformamide, neutralized with methanol, and then purified to completely isolate the aromatic polyetheramide sulfone polymer, which was carried out three times. The reduced viscosity of this polymer (01 sp7) (dimethylformamide α2% by weight solution, measured at 30°C, hereinafter the same) is 1.0 dl! /9 at nine. In addition, when we measured the glass transition temperature (Tg) of this polymer, we found that it was 6 at 260°C.
Riku.

This polymer 39 was dissolved in a 6=4 mixture*'ygtc of N-methylpyrrolidone and butyl cellosolve acetate,
3 weight-varnishes were made.

The nonapolymer varnish obtained in this manner was applied to a thoroughly cleaned glass plate having a transparent conductive film using a stainer for 20 GO.
After uniformly applying the coating at 150° C. rpm, the solvent was evaporated by drying at 150° C. for 30 minutes to form an orientation control film with a thickness of 1000. This film was rubbed in a certain direction with felt to produce a glass substrate having an orientation control film.

The alignment control films of the two glass substrates thus produced were placed facing each other, and sealed with a 92-liquid type sealant mixed with 10μ glass fibers. (Sealant curing F! 120°C for 30 minutes.) A phenylcyclohexane-based liquid crystal (Merck Co., Ltd. 11.ZLI-1132) was placed between the alignment control films of this element, and between two orthogonal polarizing plates. When the orientation of the liquid crystal was examined, it was found to be good (tilt angle 22 degrees). A cell prepared in the same manner before placing the liquid crystal was heat-treated at 200°C for 2 hours.
When ZLI-1132 liquid crystals were arranged in the same manner and the alignment of the liquid crystal was examined between two orthogonal polarizing plates, good alignment was shown (tilt angle of 12 degrees).

Example 2 A solution of 100% by weight of terephthalic acid dichloride in 10% by weight of cyclohexanone and 20% by weight of an aromatic diamine mixture consisting of 90% by weight of bis[4-(3-aminophenoxy)phenylsulfone] and 10% by weight of 44'-diaminodiphenyl ether. Add 1 cyclohexanone solution to the acid chloride and aromatic diamine in equal proportions.
The acid chloride and diamine were reacted by mixing in the presence of a 0 weight aqueous sodium hydroxide solution, and the resulting aromatic polyetheramide sulfone polymer was isolated.

This was dissolved into dimethylformamide again, and this was poured into methanol to isolate an aromatic polyetheramide sulfone polymer. The purification method was performed three times, and the glass transition temperature (Tg) of this polymer was measured. When I checked the temperature, it was 255°C.

This polymer 39 was dissolved in 979 a 6:4 mixture of dimethylimidazolidinone and phenyl cellosolve, and 3 wt.
Make varnish and mourn.

The thus obtained polymer varnish was placed on a glass plate having a transparent conductive film which had been thoroughly washed, using a spinner.
After uniformly coating the film at 180° C. for 30 minutes to evaporate the solvent, an orientation control film with a thickness of 900 Å was formed.

This film was rubbed in a certain direction with felt to produce a glass substrate having an orientation control film.

Next, two glass substrates were placed with the alignment control films facing each other, and sealed with a two-component sealant containing 10 μm glass fiber. (Sealant curing #1120℃
- Run for 30 minutes. ) Between the alignment control films of this element, phenylcyclohexane-based liquid crystal (manufactured by Merck & Co., Ltd., ZLI-
1132) and examined the alignment of the liquid crystal between two orthogonal polarizing plates, it was found that the alignment was good.
0 degrees). It was produced in the same manner. ZLI-113 was heat-treated at 200°C for 2 hours before the liquid crystal was placed on the cell.
When two liquid crystals were arranged in the same way and the alignment of the liquid crystal was examined between two orthogonal polarizing plates, good alignment was found (tilt angle 20 degrees).

Example 3 l of an acid chloride mixture consisting of 50% by weight of terephthalic acid dichloride and 50% by weight of isophthalic acid dichloride
O weight ratio is hexanone solution (4-(4-
aminophenoxy) phenyl sulfone 60% by weight and 4
4'-diaminodiphenylsulfone 33 wt.- and 1.3
-Bis(aminopropyl)tetramethyldisiloxane 7
A 20% by weight cyclohexanone solution of a diamine mixture consisting of 20% by weight is mixed in the presence of a 10% by weight aqueous sodium hydroxide solution in such a proportion that the acid chloride and diamine are equimolar, and the acid chloride and diamine are reacted. The resulting aromatic polyetheramide sulfone polymer was isolated. The glass transition temperature (Tg) of the aromatic polyetheramide sulfone polymer was measured by dissolving it again in dimethylformamide and pouring it into methanol, and it was found to be 260°C. 9. 3 g of this polymer was dissolved in 97B, a 6:4 mixture of dimethylformamide and ethyl cellosolve acetate to prepare a 3% by weight varnish.

The thus obtained polymer varnish was placed on a glass plate having a transparent conductive film which had been thoroughly washed and was heated at 2000 rpm using a spinner.
After uniformly coating the film at 120°C, the solvent was evaporated by drying at 120°C for 30 minutes to form an orientation control film with a thickness of 800λ.

This film was rubbed in a certain direction with felt to create a glass substrate with an orientation control film.

The alignment control films of the two glass substrates thus prepared were placed facing each other and sealed with a two-component type sealant mixed with 10 μm glass fiber. (The sealant was cured at 120°C for 30 minutes.) A phenylcyclohexane-based liquid crystal (Merck Co., Ltd. 11.ZLI-1132) was placed between the alignment control films of this element, and the liquid crystal was placed between two orthogonal polarizing plates. When the orientation was examined, it was found to be good (tilt angle: 41 degrees). It was prepared in the same manner. The cell was heat-treated at 200℃ for 2 hours before placing the liquid crystal,
When ZLI-1132 liquid crystals were arranged in the same manner and the alignment of the liquid crystal was examined between two orthogonal polarizing plates, good alignment was shown (tilt angle of 11 degrees).

Example 4 10% by weight cyclohexanone solution of 100% by weight of terephthalic acid dichloride and 60% by weight of bis[4-(4-aminophenoxy)phenyl]sulfone and 22-bisC
4-(4-aminophenoxy)phenyl]propane 35
A 20% by weight cyclohegisanone solution of a diamine mixture consisting of 5% by weight of 1.3-bis(aminopropyl)tetramethyldisiloxane was added to 10% by weight of water in such a proportion that the acid chloride and diamine were equimolar. The acid chloride and diamine were reacted by mixing in the presence of an aqueous sodium oxide solution, and the resulting aromatic polyetheramide sulfone polymer was isolated. This was dissolved again in dimethylformamide, poured into methanol, and the glass transition temperature (Tg) of the aromatic polyetheramitos polymer was measured and found to be 250°C.

This polymer 3 was dissolved in 979, a 5:5 mixture of N-methylpyrrolidone and butyl cellosolve acetate to prepare a 3% by weight varnish.

The thus obtained polymer varnish was placed on a glass plate having a transparent conductive film which had been thoroughly washed and was heated at 2000 rpm using a spinner.
After uniformly coating the film at 150° C., the solvent was evaporated by drying at 150° C. for 30 minutes to form an orientation control film with a thickness of 1050 Å. This film was rubbed in a certain direction with felt to produce a glass substrate having an orientation control film.

The alignment control films of the two glass substrates prepared in this manner were placed facing each other, and sealed with a two-component sealant containing 10μ glass fiber.9. (The seal cocoon was cured at 120°C for 30 minutes.) A phenylcyclohexane liquid crystal (manufactured by Merck & Co., Ltd., ZLI-1132) was placed between the alignment control films of this element, and the liquid crystal was placed between two orthogonal polarizing plates. When the orientation was examined, it was found that the orientation was good (tilt angle 40 degrees). Z
LI-1132 liquid crystals were arranged in the same manner, and the alignment of the liquid crystal was examined between two orthogonal polarizing plates, and the results showed good alignment (tilt angle of 20 degrees).

Comparative Example 1 of an acid chloride mixture consisting of 50% by weight of terephthalic acid dichloride and 50% by weight of isophthalic acid dichloride
0wt% cyclohexanone solution x□:2. z-bis (
4-(4-aminophenoxy)phenyl]propane 10
0wt $0 A 20wt% cyclohexanone solution is mixed in the presence of a 10wt aqueous sodium hydroxide solution in such a proportion that the acid chloride and diamine are equimolar, the acid chloride and the diamine are reacted, and the resulting polymer is isolated.

This was dissolved again in dimethylformamide and poured into methanol to isolate the polymer.The glass transition temperature (Tg) of this polymer was measured and was found to be 220°C.
Met.

Three parts of this polymer were dissolved in 6-4 mixture 979 of N-methylpyrrolidone and butyl cellosolve acetate to prepare a 3% by weight varnish.

The nine-polymer varnish obtained in this way was thoroughly washed and spun at 2,000 rp using a pressure spinner on a glass plate having a transparent conductive film.
After applying the film uniformly using rn, the film was dried at 150° C. for 30 minutes to evaporate the solvent, thereby forming an orientation control film with a thickness of 900 Å. This film was rubbed in a certain direction with felt to produce a glass substrate having an orientation control film.

The alignment control films of the two glass substrates thus produced were placed facing each other and sealed with a two-component type sealant mixed with 10 μm glass fiber. (The sealing agent was cured at 120°C for 30 minutes.) A phenylcyclohexane-based liquid crystal (manufactured by Merck & Co., Ltd., ZLI-1132) was placed between the alignment control films of this element, and the liquid crystal was placed between two orthogonal polarizing plates. When the orientation was examined, it was found that the orientation was good (tilt angle: 2.1 degrees). Z
When LI-1132 liquid crystals were arranged in the same space and the alignment of the liquid crystals was examined between two orthogonal polarizing plates, domains were generated near the sealant, and there were areas with poor alignment.

(Effects of the Invention) According to the present invention, by using a specific aromatic polyetheramide sulfone polymer as an alignment control film material,
An alignment control film that can be processed at a low temperature of +11100 to 200°C, that is, a film made of a specific aromatic polyetheramide sulfone polymer, can be used as a substrate material.
It is not limited to glass, but resin films or resin plates can also be used.

(2) Since the alignment control film material is a resin insoluble in water and liquid crystal, a liquid crystal display element with excellent moisture resistance can be obtained.

As a result, it is possible to provide a liquid crystal display element that is lightweight and thin, and it is also possible to obtain a liquid crystal display element that is cheaper than the conventional method.

Note that the device of the present invention can also provide color display by arranging a guest-host type liquid crystal. Moreover, one element of the present invention is T
It may also be one using PT.

Claims (1)

[Claims] 1. The alignment control film of a liquid crystal display element has a general formula (I): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ...... (I) [In the formula, R_1, R_2, R_3 and R_4 are Each independently represents hydrogen, a lower alkyl group, a lower alkoxy group, or a halogen, and Ar is a p-phenylene group, m-phenylene group, diphenylene group, naphthylene group, or ▲a mathematical formula, a chemical formula, a table, etc.▼ (in the formula, Y is -O-, -SO_2-, -C-, -S-, ▲
A liquid crystal display element containing an aromatic polyetheramide sulfone polymer having a repeating unit represented by ▼ or -CH_2-, which has mathematical formulas, chemical formulas, tables, etc.