Polymer composition and liquid crystal alignment film for transverse electric field driving liquid crystal display element

Abstract

The present invention provides a polymer composition that includes: [ I ] (A) a photosensitive branched polymer that exhibits crystallinity in a prescribed temperature range, said polymer having a side chain represented by formula (0) and further having a side chain (a) having a group selected from the group consisting of nitrogen-containing aromatic heterocyclic groups, amide groups, and urethane groups; and (B) an organic solvent. The invention further provides a method for producing a substrate that has a liquid crystal alignment film, the method having a step for forming a coating film by applying the composition to a substrate having a conductive film for driving a transverse electric field, a step for irradiating the obtained coating film with polarized UV rays, and a step for heating the obtained coating film. The invention provides a liquid crystal alignment film with excellent burn-in properties, to which an alignment control function has been imparted with high efficiency, due to the polymer composition and a transverse electric field driving liquid crystal display element.

Description

technical field

[0001] The present invention relates to a novel polymer composition, a liquid crystal alignment film for a transverse electric field-driven liquid crystal display element using the same, and a method for manufacturing a substrate having the alignment film. Furthermore, the present invention relates to a novel 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 a...

Examples

preparation example Construction

[0236] [Preparation of polymer composition]

[0237] 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.

[0238] In the polymer composition of the present embodiment, all of the above-mentioned resin components may be the above-mentioned photosensitive side chain polymers capable of exhibiting liquid crystallin...

Embodiment

[0350] Methacrylic monomers MA1 and MA2 used in Examples; GMA, HBAGE, G1 and additive T1 which are monomers having an epoxy side chain are shown below.

[0351] In addition, MA1 and MA2 were respectively synthesize|combined 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).

[0352] G1 was synthesized by the synthesis method described in Synthesis Example 1 below.

[0353] GMA (glycidyl methacrylate), HBAGE (hydroxybutyl acrylate glycidyl ether), and additive T1 (3-aminomethylpyridine) used commercially available ones.

[0354]

Synthetic example 1

[0356] Synthesis of Specific Glycidyl Compounds (C1)

[0357]

[0358] Add (COCl) to THF (tetrahydrofuran) solution (184 g) of carboxylic acid derivative (MA2) (18.4 g, 60 mmol) 2 (Oxalyl chloride) (11.4 g, 90 mmol) and 2 drops of DMF (dimethylformamide) were reacted at room temperature for 2 hours. The solid obtained by concentrating this solution was dissolved in THF (350 g). This solution was added dropwise to a THF solution (88 g) of glycidol (8.89 g, 120 mmol) and triethylamine (13.4 g, 132 mmol) over 1 hour, and reacted for 18 hours. Then, ethyl acetate (500g) was added, the organic phase was wash|cleaned 3 times with water (300g), and it dried with magnesium sulfate. After removing magnesium sulfate by filtration, it concentrated and obtained the crude product. The resulting crude product was chromatographed on silica gel using ethyl acetate and hexanes to afford C1 as a white solid. (yield: 14.9 g, yield: 69%).

[0359] Glycidyl derivatives (C1):

[0360] 1 H...

technical field

[0001] The present invention relates to a novel polymer composition, a liquid crystal alignment film for a transverse electric field-driven liquid crystal display element using the same, and a method for manufacturing a substrate having the alignment film. Furthermore, the present invention relates to a novel 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 a...

Examples

preparation example Construction

[0236] [Preparation of polymer composition]

[0237] 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.

[0238] In the polymer composition of the present embodiment, all of the above-mentioned resin components may be the above-mentioned photosensitive side chain polymers capable of exhibiting liquid crystallin...

Embodiment

[0350] Methacrylic monomers MA1 and MA2 used in Examples; GMA, HBAGE, G1 and additive T1 which are monomers having an epoxy side chain are shown below.

[0351] In addition, MA1 and MA2 were respectively synthesize|combined 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).

[0352] G1 was synthesized by the synthesis method described in Synthesis Example 1 below.

[0353] GMA (glycidyl methacrylate), HBAGE (hydroxybutyl acrylate glycidyl ether), and additive T1 (3-aminomethylpyridine) used commercially available ones.

[0354]

Synthetic example 1

[0356] Synthesis of Specific Glycidyl Compounds (C1)

[0357]

[0358] Add (COCl) to THF (tetrahydrofuran) solution (184 g) of carboxylic acid derivative (MA2) (18.4 g, 60 mmol) 2 (Oxalyl chloride) (11.4 g, 90 mmol) and 2 drops of DMF (dimethylformamide) were reacted at room temperature for 2 hours. The solid obtained by concentrating this solution was dissolved in THF (350 g). This solution was added dropwise to a THF solution (88 g) of glycidol (8.89 g, 120 mmol) and triethylamine (13.4 g, 132 mmol) over 1 hour, and reacted for 18 hours. Then, ethyl acetate (500g) was added, the organic phase was wash|cleaned 3 times with water (300g), and it dried with magnesium sulfate. After removing magnesium sulfate by filtration, it concentrated and obtained the crude product. The resulting crude product was chromatographed on silica gel using ethyl acetate and hexanes to afford C1 as a white solid. (yield: 14.9 g, yield: 69%).

[0359] Glycidyl derivatives (C1):

[0360] 1 H...

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