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Novel liquid crystal orientation agent, diamine, and polyimide precursor

A polyimide precursor, liquid crystal aligning agent technology, applied in liquid crystal materials, chemical instruments and methods, instruments, etc., can solve the problems of insufficient liquid crystal recovery, reduced contrast, close distance between pixel electrodes and general electrodes, etc. The effect of high voltage holding ratio and brush abrasion resistance

Active Publication Date: 2016-09-28
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In particular, in the liquid crystal display element of the transverse electric field method, there are few electrodes formed in the substrate, so when the voltage retention rate of the liquid crystal alignment film is weak, a sufficient voltage cannot be applied to the liquid crystal, and the display contrast is reduced. Compared with the horizontal electric field method, the distance between the pixel electrode and the common electrode of the horizontal electric field method is short, so there is the following problem: a strong electric field is applied to the alignment film and the liquid crystal layer, and these defects are easy to become obvious
If the alignment stability is lacking, the liquid crystal will not return to the initial state when the liquid crystal is driven for a long time, which will cause a decrease in contrast, afterimage or afterimage

Method used

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  • Novel liquid crystal orientation agent, diamine, and polyimide precursor
  • Novel liquid crystal orientation agent, diamine, and polyimide precursor
  • Novel liquid crystal orientation agent, diamine, and polyimide precursor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0268] Synthesis of (DA-1)

[0269]

[0270]Under a nitrogen atmosphere, dimethylformamide (390 g), 4-fluoronitrobenzene (65.0 g, 0.461 mol), 4-aminomethylpiperidine (25.0 g, 0.219 mol) and carbonic acid were added to a four-necked flask. Potassium (90.9 g, 0.658 mol) was reacted at 60°C. After heating and stirring for 22 hours, the disappearance of the intermediate was confirmed by HPLC. Thereafter, potassium carbonate was removed by filtration, and potassium carbonate was washed twice with 250 g of dimethylformamide. The obtained solution was distilled off under reduced pressure until the content became 295 g, and then 1.50 kg of water was added to precipitate the compound (11). Thereafter, the precipitate was collected by filtration and dried to obtain a crude product of compound (11). The obtained crude product was purified by recrystallization from tetrahydrofuran to obtain compound (11) (58.8 g, 0.165 mol, yield: 75.3%) as a yellow solid.

[0271] HPLC measurement...

Embodiment 2

[0286] Synthesis of (DA-2)

[0287]

[0288] Under a nitrogen atmosphere, tetrahydrofuran (534 g), compound (11) (21.4 g, 0.0601 mol) obtained by (Example 1) and potassium tert-butoxide (8.10 g, 0.0722 mol) were added to a four-necked flask. Methyl iodide (9.35 g, 0.0660 mol) was added dropwise to the stirred solution, and the temperature was raised to 40°C. After reacting for 24 hours, methyl iodide (10.2 g, 0.0717 mol) and potassium tert-butoxide (2.98 g, 0.0266 mol) were further added, and the disappearance of the raw materials was confirmed by HPLC. Thereafter, 100 g of water was added to terminate the reaction. To the crude product obtained by distilling off the reaction liquid under reduced pressure, 500 g of water was added, stirred for 24 hours in a slurry state, and the solid was filtered and dried. Thereafter, recrystallization was performed from tetrahydrofuran to obtain compound (13) (17.4 g, 0.0470 mol) as a yellow solid in a yield of 78.2%.

[0289] 1 H-NM...

Embodiment 3

[0307] Measure 1.98 g (5.00 mmol) of DA-1 into a 50 mL four-neck flask equipped with a stirring device and a nitrogen gas introduction tube, add 20.8 g of NMP, and stir while feeding nitrogen to dissolve it. While stirring this diamine solution, 1.03 g (4.75 mmol) of acid dianhydride (A) was added, and 5.20 g of NMP was further added, and stirred at 23° C. for 3 hours under a nitrogen atmosphere to obtain a polyamic acid solution (PAA-1) . The viscosity of this polyamic acid solution at a temperature of 25° C. was 134 mPa·s.

[0308] Take 7.92 g of the polyamic acid solution (PAA-1) obtained in Synthesis Example 2 into a 100 mL Erlenmeyer flask with a stirring bar, add 2.56 g of NMP, 3-glycidoxypropyltriethoxysilane The liquid crystal aligning agent (A-1) was obtained by stirring 0.67g of 1 mass % NMP solution, BCS3.72g with the magnetic stirrer for 2 hours.

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Abstract

The invention discloses a novel liquid crystal orientation agent, a diamine, and a polyimide precursor. Provided is a liquid crystal orientation agent from which it is possible to obtain a liquid crystal orientation film which has a high voltage retention rate and high rubbing resistance, and is capable of quickly reducing a stored charge, and specifically, is capable of suppressing a shift in the rubbing direction and in the liquid-crystal orientation direction in an in-plane switching device. Provided are: a polyimide precursor obtained by reacting a tetracarboxylic acid derivative component with a diamine component containing a diamine represented by formula (1); and a liquid crystal orientation agent containing one or more types of polymer selected from a group consisting of polyimides obtained by ring-closing the polyimide precursor. (R1 represents hydrogen or a monovalent organic group. Q1 represents a C1-5 alkylene group, Cy is a divalent group comprising azetidine, pyrrolidine, piperidine, or hexamethyleneimine, and a substituent group may be bonded to the ring segment of these groups. R2 and R3 are monovalent organic groups, and q and r each independently represents an integer of 0-4. In addition, when the sum of q and r is 2 or more, the plurality of R2 and R3 are as defined above.) (as shown in the description)

Description

technical field [0001] This invention relates to the novel diamine useful as a raw material of the polymer used for a novel liquid crystal aligning agent, this liquid crystal aligning agent, the polyimide precursor obtained using this diamine, and polyimide. Background technique [0002] Liquid crystal display elements have been widely used as displays in computers, mobile phones, and television receivers. As driving methods, longitudinal electric fields such as the TN (Twisted Nematic) method and the VA (Vertical Alignment) method are known. mode; IPS (In-Plane-Switching) mode, FFS (Fringe Field Switching, Fringe Field Switching) mode and other transverse electric field modes. [0003] Generally, compared with the conventional longitudinal electric field method in which liquid crystal is driven by applying voltages to electrodes formed on the upper and lower substrates, the lateral electric field method in which electrodes are formed on only one side of the substrate and an...

Claims

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Application Information

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IPC IPC(8): C07D211/26C08G73/10G02F1/1337
CPCC07D211/26C08G73/10C08G73/1082G02F1/133723C07D211/06C08G73/1003C08G73/1007C09K19/56G02F1/1337C09K2219/03
Inventor 巴幸司石井秀则石川和典坂本谦治佐久间大辅原田佳和
Owner NISSAN CHEM IND LTD
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