Diamine compound and preparation method thereof, liquid crystal alignment agent, liquid crystal alignment film, liquid crystal display element

A technology of liquid crystal alignment agent and amine compound, applied in the field of new structure diamine compound and its preparation, can solve the problems of inability to solve the problem of friction method, reduced process efficiency, insufficient environmental affinity, etc., to ensure safety and economy. Effect

Inactive Publication Date: 2015-08-05
DONGJIN SEMICHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First, because static electricity may destroy thin film transistor (TFT) devices, production machinery generally has countermeasures against static electricity, but the rubbing method has the disadvantage of not being able to provide a complete solution to the static electricity generated during the alignment process
Second, dust may be generated during the alignment process by rubbing, so a subsequent cleaning process is required, which may reduce the process efficiency
Third, the friction conditions of the flat part and the stepped part of the alignment layer with the stepped part are different from each other, so that there is a high possibility of alignment fixing force and uneven inclination angle
Fourth, the production process of the alignment layer with separated aligned pixels is complicated by rubbing in only one direction
Fifth, in order to be able to rub large substrates evenly, special equipment is also required
[0006] Therefore, there is a need for a solution that can solve the problems of poor economy, insufficient environmental affinity, poor stability, and the prepared optical patterns will lead to product performance degradation in the existing optical pattern forming process.

Method used

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  • Diamine compound and preparation method thereof, liquid crystal alignment agent, liquid crystal alignment film, liquid crystal display element
  • Diamine compound and preparation method thereof, liquid crystal alignment agent, liquid crystal alignment film, liquid crystal display element
  • Diamine compound and preparation method thereof, liquid crystal alignment agent, liquid crystal alignment film, liquid crystal display element

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preparation example Construction

[0067] The preparation method of the diamine compound represented by the chemical formula 10 comprises the following steps:

[0068] reacting the compound represented by the following Chemical Formula 6 with the compound represented by the following Chemical Formula 8 to prepare the compound represented by the following Chemical Formula 9; and

[0069] removing the protecting group PG of the compound represented by the following chemical formula 9;

[0070] [chemical formula 6]

[0071]

[0072] [chemical formula 8]

[0073]

[0074] [chemical formula 9]

[0075]

[0076] [chemical formula 10]

[0077]

[0078] In chemical formulas 6, 8, 9 and 10, n is an integer from 1 to 20; R 1 to R 8 are the same or different, and independently represent H, CN, NO2, CF3, halogen, an alkyl group with 1 to 10 carbon atoms, or an alkoxy group with 1 to 10 carbon atoms; PG is benzyloxycarbonyl (carbobenzyloxy, Cbz), p-Methoxybenzyl carbonyl (p-Methoxybenzyl carbonyl, Moz), te...

preparation Embodiment 1

[0201] Preparation of Chemical Formula 10 (n=1, R 1 ～R 8 =H, when PG=BOC) compound

[0202] [Reaction Formula Ⅰ]

[0203]

[0204] Dissolve 95.0 g (0.74 mol) of the raw material 4,4,4-trifluorobutan-1-ol (chemical formula 1) in 135 ml (0.97 mol) of triethylamine (TEA) and 1 L of dichloromethane (Methylene Chloride, MC) and cooled to 0°C. To the resulting material was slowly added 63.0 ml (62.0 ml) of methanesulfonyl chloride (MsCl) over 30 minutes. The mixture was stirred at 0°C for 10 minutes and allowed to react at room temperature for 2 hours to prepare 4,4,4-trifluorobutyl methanesulfonate (4,4,4-trifluorobutyl methanesulfonate) (Chemical Formula 2 ).

[0205] The compound of chemical formula 2 was detected by NMR, and the results were as follows.

[0206] 1 H NMR (400MHz, CDCl 3 ) δ4.30 (t, 2H), 3.04 (s, 3H), 2.28 (m, 2H), 2.05 (m, 2H)

[0207] [Reaction Formula Ⅱ]

[0208]

[0209] Next, 75.9g (0.56mol) of 4-hydroxyacetophenone (4-hydroxyacetophe...

preparation Embodiment 2

[0228] Preparation of the compound of chemical formula 23 (n=1, R1~R8=H, PG=BOC)

[0229] [Reaction Formula Ⅵ]

[0230]

[0231] 95.0 (0.74mol) of the raw material 4,4,4-trifluorobutan-1-ol (chemical formula 1) was dissolved in 135ml (0.97mol) of triethylamine and 1L of dichloromethane, and within 30 minutes At 0°C, 63.0ml (0.81mol) of methanesulfonyl chloride (methanesulfonyl chloride, MsCl) was slowly added. The mixture was stirred at 0°C for 10 minutes, and reacted at room temperature for 2 hours to prepare 4,4,4-trifluorobutyl methanesulfonate (Chemical Formula 2).

[0232] The compound of chemical formula 2 was detected by NMR, and the results were as follows.

[0233] 1 H NMR (400MHz, CDCl 3 ) δ4.30 (t, 2H), 3.04 (s, 3H), 2.28 (m, 2H), 2.05 (m, 2H)

[0234] [Reaction formula VII]

[0235]

[0236] Dissolve 72.5g (0.53mol) of 4-hydroxyacetophenone (4-hydroxyacetophenone) (chemical formula 3) in 700mL of DMF, and make it with 152g (0.64mol) of methanesulfonic...

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Abstract

The present invention relates to an amine compound, a method for preparing same, and a liquid crystal alignment agent, a liquid crystal alignment film, and a liquid crystal display device, having same. A liquid crystal alignment agent having polyamic acid or polyimide prepared using the amine compound of the present invention enables a liquid crystal alignment film and a liquid crystal display device having an excellent thermal stability even after forming the liquid crystal alignment film, and expressing high alignment and stability even after an ultraviolet ray irradiation.

Description

[0001] This application claims priority based on Korean Patent No. 10-2011-0047028 filed with the Korean Intellectual Property Office on May 18, 2011 and Korean Patent No. 10-2011-0047030 filed with the Korean Intellectual Property Office on May 18, 2011 , the entire contents of these patents are incorporated in this application by reference. technical field [0002] The invention relates to a diamine compound and a preparation method thereof, a liquid crystal alignment agent, a liquid crystal alignment film and a liquid crystal display element. More specifically, it relates to a new structural diamine compound that can be used as an optical alignment agent, a preparation method thereof, a liquid crystal alignment agent, a liquid crystal alignment film, and a liquid crystal display element. Background technique [0003] In the structural material of the liquid crystal display, the liquid crystal alignment film is in contact with the liquid crystal molecules to align the liqu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C225/22C07C221/00C08G73/10C09K19/56
CPCG02F1/133723C09K19/56C07C225/22C08G73/10C08L79/08G02F1/1337
Inventor 李成奎崔珍郁安龙昊苏相琓
Owner DONGJIN SEMICHEM CO LTD
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