Method for producing substrate having liquid crystal alignment film for transverse electric field driving type liquid crystal display elements

Abstract

The present invention provides a highly reliable transverse electric field driving type liquid crystal display element which is provided with alignment control ability at high efficiency and has excellent screen burn-in characteristics. The present invention provides a method for producing a substrate having a transverse electric field driving type liquid crystal alignment film, in which a liquid crystal alignment film for transverse electric field driving type liquid crystal display elements provided with alignment control ability is obtained by performing: [I] a step for forming a coating film by applying a polymer composition to a substrate having a conductive film for transverse electric field driving, said polymer composition containing (A) a photosensitive side-chain polymer which exhibits liquid crystallinity within a predetermined temperature range, and which has one or more repeating units that are selected from among cyclic amine structures wherein two carbon atoms adjacent to a nitrogen atom respectively have two substituents represented by formula (S) (wherein R11 represents a single bond or the like, X represents a single bond and R12 represents a hydrocarbon group), and (B) an organic solvent; [II] a step for irradiating the coating film obtained in step [I] with polarized ultraviolet light; and [III] a step for heating the coating film obtained in step [II].-R11-X-R12(S).

Description

technical field

[0001] The present invention relates to a method for manufacturing a substrate having a liquid crystal alignment film for a transverse electric field drive type liquid crystal display element. More specifically, it relates to a new method for producing a liquid crystal display element excellent in image sticking characteristics. Background technique

[0002] Liquid crystal display devices are known as display devices that are light in weight, thin in cross-section, and low in power consumption. In recent years, they have been used in large-scale television applications, etc., and have achieved remarkable development. The liquid crystal display element is constituted, for example, by sandwiching a liquid crystal layer between a pair of transparent substrates provided with electrodes. Also, in a liquid crystal display element, an organic film containing an organic material is used as a liquid crystal alignment film to bring liquid crystals into a desired align...

Examples

preparation example Construction

[0362] [Preparation of polymer composition]

[0363] The polymer composition used in the present invention is preferably prepared in the form of a coating liquid so as to be suitable for forming a liquid crystal aligning film. That is, the polymer composition used in the present invention is preferably prepared in the form of a solution in which a resin component for forming a resin coating is dissolved in an organic solvent. Here, the resin component refers to a resin component containing the above-mentioned photosensitive side chain type polymer capable of expressing liquid crystallinity. In this case, the content of the resin component is preferably 1% by mass to 20% by mass, more preferably 3% by mass to 15% by mass, particularly preferably 3% by mass to 10% by mass.

[0364] In the polymer composition of this embodiment, the above-mentioned resin components may all be the above-mentioned photosensitive side-chain polymers capable of exhibiting liquid crystallinity,...

Embodiment

[0434] The methacrylic monomers MA1 to MA5 used in Examples are shown below.

[0435] In addition, MA1 and M2 were respectively synthesized as follows. That is, MA1 was synthesized by the synthesis method described in the patent document (WO2011-084546). MA2 was synthesized by the synthesis method described in the patent document (Japanese Patent Laid-Open No. 9-118717).

[0436] A commercially available product was used for MA3.

[0437] MA4 used commercially available M6BC (manufactured by Midori Chemical Co., Ltd.).

[0438] MA5 is a novel compound that has not been disclosed in literature or the like. MA5 was synthesized using MA2 and MA5-1, the details of which are described in "" below. It should be noted that MA5-1 was synthesized by the synthesis method described in literature (LiquidCrystals (2005), 32(8), 1031-1044.).

[0439]

[0440] In addition, the abbreviations of the reagents used in this example are shown below.

[0441] (Organic solv...

Synthetic example 1

[0455] MA1 (1.99g, 6.0mmol), MA2 (7.35g, 24.0mmol), MA3 (0.33g, 1.5mmol) were dissolved in THF (85.45g), and after degassing with a diaphragm pump, AIBN (0.246g, 1.5 mmol) and degassed again. Then, it was made to react at 50 degreeC for 24 hours, and the polymer solution of the methacrylate was obtained. This polymer solution was added dropwise to diethyl ether (2000 ml), and the resulting precipitate was filtered. This deposit was wash|cleaned with diethyl ether, and it dried under reduced pressure in the oven of 40 degreeC, and obtained the methacrylate polymer powder.

[0456] NMP54.0g was added to the obtained powder 6.0g, and it stirred at room temperature for 3 hours. BC (40.0g) was added and stirred to this solution, and liquid crystal aligning agent solution A1 was obtained.

technical field

[0001] The present invention relates to a method for manufacturing a substrate having a liquid crystal alignment film for a transverse electric field drive type liquid crystal display element. More specifically, it relates to a new method for producing a liquid crystal display element excellent in image sticking characteristics. Background technique

[0002] Liquid crystal display devices are known as display devices that are light in weight, thin in cross-section, and low in power consumption. In recent years, they have been used in large-scale television applications, etc., and have achieved remarkable development. The liquid crystal display element is constituted, for example, by sandwiching a liquid crystal layer between a pair of transparent substrates provided with electrodes. Also, in a liquid crystal display element, an organic film containing an organic material is used as a liquid crystal alignment film to bring liquid crystals into a desired align...

Examples

preparation example Construction

[0362] [Preparation of polymer composition]

[0363] The polymer composition used in the present invention is preferably prepared in the form of a coating liquid so as to be suitable for forming a liquid crystal aligning film. That is, the polymer composition used in the present invention is preferably prepared in the form of a solution in which a resin component for forming a resin coating is dissolved in an organic solvent. Here, the resin component refers to a resin component containing the above-mentioned photosensitive side chain type polymer capable of expressing liquid crystallinity. In this case, the content of the resin component is preferably 1% by mass to 20% by mass, more preferably 3% by mass to 15% by mass, particularly preferably 3% by mass to 10% by mass.

[0364] In the polymer composition of this embodiment, the above-mentioned resin components may all be the above-mentioned photosensitive side-chain polymers capable of exhibiting liquid crystallinity,...

Embodiment

[0434] The methacrylic monomers MA1 to MA5 used in Examples are shown below.

[0435] In addition, MA1 and M2 were respectively synthesized as follows. That is, MA1 was synthesized by the synthesis method described in the patent document (WO2011-084546). MA2 was synthesized by the synthesis method described in the patent document (Japanese Patent Laid-Open No. 9-118717).

[0436] A commercially available product was used for MA3.

[0437] MA4 used commercially available M6BC (manufactured by Midori Chemical Co., Ltd.).

[0438] MA5 is a novel compound that has not been disclosed in literature or the like. MA5 was synthesized using MA2 and MA5-1, the details of which are described in "" below. It should be noted that MA5-1 was synthesized by the synthesis method described in literature (LiquidCrystals (2005), 32(8), 1031-1044.).

[0439]

[0440] In addition, the abbreviations of the reagents used in this example are shown below.

[0441] (Organic solv...

Synthetic example 1

[0455] MA1 (1.99g, 6.0mmol), MA2 (7.35g, 24.0mmol), MA3 (0.33g, 1.5mmol) were dissolved in THF (85.45g), and after degassing with a diaphragm pump, AIBN (0.246g, 1.5 mmol) and degassed again. Then, it was made to react at 50 degreeC for 24 hours, and the polymer solution of the methacrylate was obtained. This polymer solution was added dropwise to diethyl ether (2000 ml), and the resulting precipitate was filtered. This deposit was wash|cleaned with diethyl ether, and it dried under reduced pressure in the oven of 40 degreeC, and obtained the methacrylate polymer powder.

[0456] NMP54.0g was added to the obtained powder 6.0g, and it stirred at room temperature for 3 hours. BC (40.0g) was added and stirred to this solution, and liquid crystal aligning agent solution A1 was obtained.

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