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Diamine compound for preparing liquid crystal aligning agent and application of diamine compound

A liquid crystal aligning agent, amine compound technology, applied in liquid crystal materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of poor stability, electrostatic interference, poor orientation, etc., and achieve good electron transmission ability and antistatic performance. Strong and good orientation effect

Active Publication Date: 2019-02-22
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] With the continuous expansion of the application range of LCD, electrostatic interference will appear in many cases. If anti-static treatment is not performed in advance, the part on the electrostatic induction will be displayed for a long time, resulting in the failure to display the required content normally; at the same time during the production process The static electricity generated during the rubbing alignment process, which is currently the most popular in the industry, can easily break through the alignment layer, resulting in a short circuit or poor alignment of the liquid crystal cell. The antistatic properties of oriented films are becoming more and more stringent
[0005] In order to eliminate static interference, the following three methods are currently used: using antistatic polarizers, using antistatic TOP materials or adding antistatic agents to liquid crystals, but the above methods have certain limitations, such as bottom Color restrictions, poor stability and rising costs, etc.

Method used

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  • Diamine compound for preparing liquid crystal aligning agent and application of diamine compound
  • Diamine compound for preparing liquid crystal aligning agent and application of diamine compound
  • Diamine compound for preparing liquid crystal aligning agent and application of diamine compound

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0052] The compound represented by structural formula (1-1) can be synthesized according to the following synthetic route 1:

[0053]

[0054] (1) Synthesis of compound b-1-1a

[0055] 2,8-dihydroxydibenzosulfolane (24.8g, 100mmol), p-nitrochlorobenzene (33.1g, 210mmol), anhydrous potassium carbonate (8.28g, 210mmol) were put into a 1000mL three-necked round bottom flask. 60 mmol) and 300 g of toluene, the bath temperature was raised to 110 °C, stirred and refluxed for 3 hours, followed by TLC until the raw material 2,8-dihydroxydibenzosulfolane had no remaining, the system was lowered to room temperature, the stirring was stopped, and the reaction solution was transferred. In the separatory funnel, wash with water until neutral, remove the solvent toluene to obtain a yellow solid, add 240 g of absolute ethanol and 120 g of THF, stir for 30 min, and filter with suction, and dry the filter cake to obtain 41.69 g of yellow crystals. The product is measured by HPLC-MS, m / z= 4...

Synthetic example 2

[0060] The compounds represented by the structural formulae (1-2) to (1-4) can be synthesized according to the synthetic route 1 by using each dibenzosulfolane compound and each parent nitrobenzene compound. The specific yield, high-resolution mass spectrometry results and elemental analysis results of each product are shown in Table 1 below. In Table 1, Synthesis Examples 2-4, high-resolution mass spectrometry is HPLC-MC, and [M+1] is used to characterize the corresponding compound The molecular ion peak of :

[0061] Table 1 Yield, mass spectrum and elemental analysis data of each compound in Synthesis Examples 2-4

[0062]

Synthetic example 5

[0064] The compound represented by structural formula (1-5) can be synthesized according to the following synthetic route 2:

[0065]

[0066] (1) Synthesis of compound b-1-5a

[0067] 3,7-dicarboxydibenzosulfolane (30.43 g, 100 mmol), 3-fluoro-4-nitrophenol (32.99 g, 210 mmol), DCC (43.30 g) were put into a 1000 mL three-necked round-bottomed flask , 210 mmol) and 500 g of toluene, the bath temperature was raised to 110 ° C and stirred for 3 hours, followed by TLC until the raw material 3,7-dicarboxydibenzosulfolane had no residue, the system was lowered to room temperature and suction filtered, and the filtrate was concentrated to weight For 140g, add 200g of ethanol, a yellow solid is precipitated, suction filtration, dry the filter cake to obtain 44.81g of yellow crystals, the product is detected by HPLC-MS, m / z=582.02, confirmed to be the target product b-1-5a, with 3, Using 7-dicarboxydibenzosulfolane as a standard calculation, the reaction yield was 82%.

[0068] (...

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Abstract

The invention relates to a diamine compound for preparing a liquid crystal aligning agent and application of the diamine compound, and belongs to the technical field of liquid crystal display. The diamine compound contains bisbenzosulfolane conjugated groups and thus has the good electronic transmission capability, and a prepared liquid crystal display element has the antistatic characteristic; and meanwhile, bisbenzosulfolane is of a rigid structure, and thus the prepared liquid crystal display element has the characteristics of high stability and the excellent aligning property. A liquid crystal aligning film and the liquid crystal display element which are prepared through the liquid crystal aligning agent are high in antistatic performance, high in stability and excellent in aligning property, thus the image display quality of the liquid crystal display element is improved, the service life of a product is prolonged, and the product yield is increased, and the diamine compound canbe used for various modes of LCD devices having special requirements for static electricity.

Description

technical field [0001] The invention relates to a diamine compound used for preparing a liquid crystal aligning agent and its application, and belongs to the technical field of liquid crystal display. Background technique [0002] Liquid crystal display elements are classified into various modes according to the electrode structure and the physical properties of the liquid crystal molecules used. Currently known liquid crystal display devices can be divided into: TN type (twisted nematic type), STN type (super twisted nematic type), VA type (vertically oriented type), IPS type (in-plane switching type), FFS type (fringe field switching type) or OCB type (optically compensated bending type). [0003] The liquid crystal alignment film materials used in various liquid crystal display elements mainly include polyamic acid, polyimide, polyamide, polyester and other resin materials. Among them, polyamic acid or polyimide has excellent high temperature resistance. , mechanical str...

Claims

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Application Information

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IPC IPC(8): C07D333/76C09K19/34C09K19/56C08G73/10
CPCC07D333/76C08G73/1085C09K19/3491C09K19/56
Inventor 李士东解万龙王明佼王治国周银波胡葆华
Owner JIANGSU SUNERA TECH CO LTD
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