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Polyamic acid ester liquid crystal alignment agent, and liquid crystal alignment film using same

A technology of liquid crystal aligning agent and polyamic acid ester, which is applied in coatings, instruments, optics, etc., can solve the problems of unimproved properties of polyimide liquid crystal aligning agents, high volume resistivity, and high residual charge. Achieve the effect of improving reliability, improving electrical characteristics, and improving interface characteristics

Active Publication Date: 2013-01-23
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, polyamic acid ester usually has problems such as high volume resistivity and high residual charge when DC voltage is applied.
But, there is no method for improving the characteristics of the polyimide liquid crystal aligning agent containing polyamic acid ester at present

Method used

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  • Polyamic acid ester liquid crystal alignment agent, and liquid crystal alignment film using same
  • Polyamic acid ester liquid crystal alignment agent, and liquid crystal alignment film using same
  • Polyamic acid ester liquid crystal alignment agent, and liquid crystal alignment film using same

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1）A-5

[0362] (Synthesis Example 1) Synthesis of A-5

[0363] The diamine compound (A-5) was synthesized through the four-step route shown below.

[0364] Step 1: Synthesis of compound (A5)

[0365] [Chemical 58]

[0366]

[0367] Add propargylamine (8.81g, 160mmol), N,N-dimethylformamide (112mL), and potassium carbonate (18.5g, 134mmol) in sequence in a 500mL eggplant-shaped flask to make it 0°C, and use A solution obtained by dissolving tert-butyl bromoacetate (21.9 g, 112 mmol) in N,N-dimethylformamide (80 mL) was added dropwise with stirring for about 1 hour. After completion of the dropwise addition, the reaction solution was brought to room temperature and stirred for 20 hours. Then, the solid content was removed by filtration, 1 L of ethyl acetate was added to the filtrate, and the mixture was washed four times with 300 mL of water and once with 300 mL of saturated brine. Then, the organic layer was dried over magnesium sulfate, and the solvent was distilled off under r...

Synthetic example 2）A-2

[0380] (Synthesis Example 2) Synthesis of A-2

[0381] The diamine compound (A-2) was synthesized by the 2-step route shown below.

[0382] Step 1: Synthesis of compound (A8)

[0383] [Chemical 61]

[0384]

[0385] Add 2-iodo-4-nitroaniline (5.11g, 19.4mmol), bis(triphenylphosphine)palladium(II) dichloride (281.7mg, 0.401mmol) into a four-necked flask replaced with nitrogen, iodine Copper chloride (160.7mg, 0.844mmol) and 30ml of diethylamine were stirred at room temperature (20°C) for 10 minutes. Then, t-butyl N-propargylglycine (compound (5)) (3.72 g, 24.0 mmol) was added, and the mixture was stirred at room temperature (20° C.) for 4 hours. After confirming the disappearance of the raw materials by HPLC, 200 ml of ethyl acetate and 200 ml of a 1M ammonium chloride aqueous solution were added for extraction. The obtained organic layer was washed twice with a 1M aqueous ammonium chloride solution, and dried over anhydrous magnesium sulfate. After removing the desicca...

Synthetic example 3

[0390]Make a 3L four-necked flask with a stirring device a nitrogen atmosphere, add 44.04g (0.407mol) of p-phenylenediamine, 43.59g (0.115mol) of diamine (A-5), add NMP 1891g and pyridine as a base 92.19g (1.17mol), stirred to dissolve. Next, stirring this diamine solution, 157.90 g (0.486 mol) of 1,3DM-CBDE-Cl was added, and it was made to react under water cooling for 4 hours. 2101 g of NMP was added to the obtained polyamic acid ester solution, it stirred for 30 minutes, and the polyamic acid ester solution which can obtain 5 weight% of solid content was obtained. The obtained polyamic acid ester solution was added to 21012g of water while being stirred, and the precipitated white precipitate was filtered out, followed by washing once with 21012g of water, once with 21012g of ethanol, and three times with 5253g of ethanol. After drying, 175.94 g of white polyamic acid ester resin powder was obtained. The yield was 83.7%. Moreover, the molecular weight of this polyamic ac...

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Abstract

Disclosed is a liquid crystal alignment agent which can reduce microscopic irregularities on the surface of liquid crystal alignment films, improves liquid crystal alignment properties, and has improved electrical characteristics of every kind. The liquid crystal alignment agent contains component (A), component (B) and component (C). Component (A): a polyamic acid ester obtained from a tetracarboxylic acid dialkyl ester derivative containing a tetracarboxylic acid dialkyl ester derivative represented by general formula (1) as at least 60 mol% of the total tetracarboxylic acid dialkyl ester derivative, and a diamine containing at least one diamine selected from the diamines represented by general formulae (2-5). Component (B): a polyamic acid obtained from a tetracarboxylic acid dianhydride, and a diamine. Component (C): a mixed solvent containing at least one type of organic solvent (C1) selected from a group comprising -butyrolactone and derivatives thereof, and at least one type of organic solvent (C2) selected from a group comprising N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, and derivatives thereof, and in which the content of the organic solvent (C2) is 2%-30% by mass relative to the total amount of both organic solvents (C1, C2). (In general formula (1), R1 is a C1-5 alkyl group, and R2 is a hydroxyl group or a chlorine atom.) (In general formulae (2-5), A1 is a single bond, an ester bond, an amide bond, thioester bond, or a C2-10 divalent organic group, A2 is a halogen atom, a hydroxyl group, an amino group, a thiol group, a nitro group, a phospate group, or a C1-20 monovalent organic group, a is an integer from 1-4, and when a is 2 or higher, the structure of A2 can be the same or different).

Description

technical field [0001] This invention relates to the liquid crystal aligning agent containing the polyamic acid ester used for producing a liquid crystal aligning film, and the liquid crystal aligning film obtained from this liquid crystal aligning agent. Background technique [0002] The liquid crystal display element used for a liquid crystal television, a liquid crystal display, etc. is normally provided with the liquid crystal aligning film for suppressing the orientation state of a liquid crystal in an element. So far, as a liquid crystal aligning film, a liquid crystal aligning agent mainly composed of a polyimide precursor such as polyamic acid (polyamic acid) or a solution of a soluble polyimide is applied to a glass substrate and fired. Polyimide liquid crystal alignment film. [0003] With the high-definition of liquid crystal display elements, considering the requirements for the control of the contrast reduction of liquid crystal display elements and the reducti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G02F1/1337C08G73/10
CPCC09D179/08G02F1/1337C08G73/1075C08G73/1078C08L79/08C08L2205/02
Inventor 作本直树野口勇步长尾将人饭沼洋介
Owner NISSAN CHEM IND LTD
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