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Diamine compound as well as preparation method and application thereof

A kind of amine compound and compound technology, applied in the field of diamine compound and its preparation, can solve the problems of image afterimage, difficult ionic charge detachment, etc., and achieve the effect of simple preparation process, low residual DC charge, and easy promotion

Active Publication Date: 2020-09-29
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, when a voltage is applied to the liquid crystal display, the generated ionic charges will be absorbed by the liquid crystal alignment film, and even after the applied voltage is released, it is difficult to detach the ionic charges from the liquid crystal alignment film , resulting in the problem of afterimages on the screen

Method used

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  • Diamine compound as well as preparation method and application thereof
  • Diamine compound as well as preparation method and application thereof
  • Diamine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] A diamine compound, its structural formula is:

[0059]

[0060] The synthetic route for preparing compound I-1 is as follows:

[0061]

[0062] Specific steps are as follows:

[0063] (1) Synthesis of compound I-b-1

[0064] Add 28.8g of compound I-a-1 and 200ml of tetrahydrofuran into the reaction kettle, pass ammonia gas at room temperature until the pressure is 0.5MPa-1.0Mpa, raise the temperature to 200°C for 6 hours, lower the temperature and reduce the pressure, and quench the reaction with saturated aqueous sodium bicarbonate solution. Conventional post-treatment, recrystallization from n-heptane gave 28.6 g of off-white solid (compound I-b-1), HPLC: 99.6%, yield 87.2%;

[0065] (2) Synthesis of compound I-1

[0066] Under the protection of nitrogen, add 25.0g I-b-1 and 200ml tetrahydrofuran to the reaction bottle, add 66.5g diethylaminosulfur trifluoride dropwise under temperature control -70℃~-60℃, and react under temperature control -70℃~-60℃ 1 hour...

Embodiment 2

[0070] A diamine compound, its structural formula is:

[0071]

[0072] The synthetic route for preparing compound 1-3 is as follows:

[0073]

[0074] (1) Synthesis of compound I-c-1

[0075] Add 55.0g of compound I-b-1 and 250ml of tetrahydrofuran into the reaction bottle, add 13.5g of potassium borohydride aqueous solution dropwise at a temperature of 10°C to 30°C, and react for 3 hours at a temperature of 50°C to 60°C after dropping, then add dilute hydrochloric acid to quench the reaction. After conventional post-treatment, recrystallization from n-heptane gave 51.5 g of off-white solid (compound I-c-1), HPLC: 99.2%, yield 92.8%;

[0076] (2) Synthesis of compound I-3

[0077] Under the protection of nitrogen, add 50.0g I-c-1, 300ml tetrahydrofuran to the reaction bottle, add 86.8g diethylaminosulfur trifluoride dropwise under temperature control -70℃~-60℃, and react under temperature control -70℃~-60℃ 1 hour, naturally return to -30°C, add saturated aqueous sodi...

experiment example 1

[0081] 15.9 grams (0.05 moles) of compound I-1, 9.8 grams (0.05 moles) of CBDA were dissolved in 92.8 grams of NMP (N-methylpyrrolidone), reacted at room temperature for 12 hours, and then added 348 grams of NMP to carry out Dilute to obtain a polyamic acid solution (specific viscosity: 0.57dl / g).

[0082] Then, the polyamic acid solution was spin-coated on a glass substrate with a transparent electrode at 3000 rpm.

[0083] Then, it was heated at 200° C. for 30 minutes to form a polyimide film, which was assembled into a liquid crystal cell assembled in a parallel direction by using a spacer of 40 μm. After pouring liquid crystal (model: BYLC-1000, manufactured by Bayi Space-Time Liquid Crystal Technology Co., Ltd.), the liquid crystal cell rotates between the orthogonal Nicol prisms and presents a state of total darkness, which is obtained by using a pre-tilt angle measuring machine. The value of the pretilt angle is 87°; after testing, the residual DC charge is 93mV.

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Abstract

The invention relates to the field of liquid crystal materials, in particular to a diamine compound and a preparation method and application thereof. The structure of the diamine compound is shown asa formula I in the specification. When the diamine compound is prepared, a compound I-a raw material reacts with ammonia gas to obtain a compound I-b, and the compound I-b reacts with a fluorinating reagent to obtain a compound I. The invention further provides application of the diamine compound in the field of liquid crystal display. The provided diamine compound can improve the efficiency of aliquid crystal display element, and the prepared polyamide acid, polyimide and liquid crystal alignment agent all have good properties such as chemical stability and thermal stability, so that a formed liquid crystal alignment film has a higher pre-tilt angle; the prepared liquid crystal display element has fewer residual direct current charges, and thus the liquid crystal display element has higher efficiency. The preparation method is stable and efficient, raw materials are easy to obtain, the preparation process is simple, and popularization of the diamine compound is facilitated.

Description

technical field [0001] The invention relates to the field of liquid crystal materials. Specifically, it relates to a diamine compound and its preparation method and application. Background technique [0002] Among liquid crystal displays, a twisted nematic (TN) field effect type liquid crystal display using a nematic liquid crystal having a positive dielectric anisotropy is typical. Generally speaking, liquid crystal molecules are placed between a pair of substrates containing electrodes, and the alignment directions of the two substrates are perpendicular to each other, and the arrangement of liquid crystal molecules can be controlled by controlling the electric field. For this type of liquid crystal display, it is very important to form an alignment with a uniform tilt angle between the long axis direction of the liquid crystal molecules and the surface of the substrate. The material that aligns the liquid crystal molecules in a uniform pretilt angle is generally called ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/38C07C209/74C09K19/56C09K19/52G02F1/1337C08G73/10C08J5/18C08L79/08
CPCC07C211/38C09K19/56C09K19/542G02F1/133723G02F1/133711C08G73/10C08J5/18C07C2603/90C08J2379/08
Inventor 戴雄张嫣然高立龙储士红田会强姜天孟陈海光
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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