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Liquid crystal aligning agent for forming liquid crystal alignment film, liquid crystal alignment film and liquid crystal display device using the same

A liquid crystal aligning agent, the technology of making tetracarboxylic dianhydride, applied in liquid crystal materials, optics, instruments, etc., can solve problems such as inability to prevent poor display, insufficient film hardness, and scratches on liquid crystal alignment films

Active Publication Date: 2016-09-28
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, if this kind of photo-alignment film is applied to an actual liquid crystal display element, since the film hardness is low compared with the liquid crystal alignment film widely used in the rubbing method, there is the following problem: Fine scratches are generated on the alignment film, and the resulting foreign matter degrades the display quality of the liquid crystal display element
However, it is known that adding such a crosslinking agent can improve the film hardness, but the orientation of the liquid crystal will be greatly reduced, and in the case of an FFS mode liquid crystal display element, after driving for a long time, afterimages will occur.
In addition, there is also a crosslinking agent that does not reduce the orientation of liquid crystals, but the film hardness is insufficient for such a crosslinking agent, and when it is used as a liquid crystal display element, it is impossible to prevent damage caused by scratches on the liquid crystal alignment film. show bad generation

Method used

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  • Liquid crystal aligning agent for forming liquid crystal alignment film, liquid crystal alignment film and liquid crystal display device using the same
  • Liquid crystal aligning agent for forming liquid crystal alignment film, liquid crystal alignment film and liquid crystal display device using the same
  • Liquid crystal aligning agent for forming liquid crystal alignment film, liquid crystal alignment film and liquid crystal display device using the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0614] Hereinafter, the present invention will be described by way of examples. In addition, the evaluation methods and compounds used in the examples are as follows.

[0615]

[0616] 1. Weight average molecular weight (Mw)

[0617] The weight average molecular weight of a polyamic acid is calculated|required by the GPC method using 2695 separation module · 2414 differential refractometers (made by Waters), and performing polystyrene conversion. The polyamic acid obtained was diluted with a phosphoric acid-dimethylformamide (DMF) mixed solution (phosphoric acid / DMF=0.6 / 100: weight ratio) so that the polyamic acid concentration became about 2 wt%. HSPgel RT MB-M (manufactured by Waters) was used as a column, and the mixed solution was used as a developing solvent, and the measurement was performed under the conditions of a column temperature of 50° C. and a flow rate of 0.40 mL / min. As the standard polystyrene, TSK standard polystyrene manufactured by Tosoh Co., Ltd. was u...

Synthetic example 1

[0650] [Synthesis Example 1] Synthesis of Compounds Represented by Formula (1-4)

[0651]

[0652] Construction of cyclohexene ring

[0653]

[0654] 1,7-octadiene (50.0 g, 453.7 mmol) and 1,3-butadiene (73.6 g, 1360 mmol) were added to a 1,000 mL three-necked flask equipped with a thermometer and a reflux tube, and 500 mL of xylene was added thereto. The solution was stirred at reflux for 48 hours. The solvent was distilled off under reduced pressure to obtain a crude product. The obtained precursor was purified by silica gel column chromatography to obtain the following compounds. Yield 52.1 g, yield 53%.

[0655]

[0656] Epoxylation

[0657]

[0658] Into a 1000 mL three-necked flask equipped with a thermometer and a reflux tube, the compound (50.0 g, 229.0 mmol) obtained in the first stage was charged, and 100 mL of dichloromethane was added thereto. A dichloromethane solution (200 mL) of m-chloroperoxybenzoic acid (158.0 g, 915.8 mmol) was added dropwis...

Synthetic example 2

[0660] [Synthesis Example 2] Synthesis of Compounds Represented by Formula (1-5)

[0661]

[0662] Construction of cyclohexene ring

[0663]

[0664] In a 300mL three-necked flask equipped with a thermometer and a reflux tube, add 1,11-dodecanadiene (10.0g, 60.1mmol) and 1,3-butadiene (9.76g, 180.4mmol), and add di Toluene 100mL. The solution was stirred under reflux for 48 hours, and then, the solvent was distilled off under reduced pressure to obtain a crude product. The obtained precursor was purified by silica gel column chromatography to obtain the following compounds. Yield 5.3 g, 32% yield.

[0665]

[0666] Epoxylation

[0667]

[0668] Into a 300 mL three-necked flask equipped with a thermometer and a reflux tube, the compound (5.0 g, 18.2 mmol) obtained in the first stage was charged, and 20 mL of dichloromethane was added thereto. A dichloromethane solution (40 mL) of m-chloroperoxybenzoic acid (12.6 g, 72.9 mmol) was added dropwise while cooling t...

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PUM

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Abstract

The invention relates to a liquid crystal aligning agent, a liquid crystal alignment film, and a liquid crystal display element; the liquid crystal aligning agent comprises at least one of the following compound represented by the formula (1); the liquid crystal aligning agent can form the liquid crystal alignment film with high hardness and excellent liquid alignment performance, and the film is hard to scratch; the liquid crystal display element using the liquid crystal aligning film cannot have bad bright spot caused by foreign matters, and display feature is excellent; in the formula 1, R1 represents a single bond, carbon number 1-8 linear chain alkylene, carbon number 2-8 branch chain alkylene, or carbon number 3-8 divalent organic group with an alicyclic structure.

Description

technical field [0001] The present invention relates to a liquid crystal aligning agent containing polyamic acid or its derivatives and a specific compound, a liquid crystal aligning film formed using the liquid crystal aligning agent, and a liquid crystal display element including the liquid crystal aligning film. Background technique [0002] Monitors of personal computers, LCD TVs, View Finders of video cameras, projection displays and other display devices, and optoelectronics such as optical printing heads, optical Fourier transform elements, and light valves )-related components and the like, and the mainstream of liquid crystal display elements that have been commercialized and widely distributed today are display elements using nematic liquid crystals. The display modes of nematic liquid crystal display elements are widely known as twisted nematic (Twisted Nematic, TN) mode and super twisted nematic (Super Twisted Nematic, STN) mode. In recent years, in order to imp...

Claims

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Application Information

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IPC IPC(8): C09K19/56G02F1/1337
CPCC09K19/542C09K19/56G02F1/133723
Inventor 小口雄二郎森隆浩
Owner JNC CORP
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