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Liquid crystal aligning agent, liquid crystal aligning film and liquid crystal display element

A technology of liquid crystal alignment agent and liquid crystal alignment film, which is applied in the new diamine field, can solve the problems of liquid crystal alignment film scars, defects, and insufficient mechanical strength of rubbing treatment, and achieve high reliability.

Active Publication Date: 2015-08-05
NISSAN CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In recent years, when firing polyimide-based liquid crystal alignment films at low temperatures, insufficient mechanical strength of the film against rubbing has become a problem.
That is, there are defects such as scratches on the surface of the liquid crystal alignment film and a part of the film being peeled off from the substrate during the rubbing treatment.
In low-temperature firing, since the strength of the film is insufficient compared with the usual firing temperature, the defects caused by the rubbing treatment become a more serious problem.

Method used

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  • Liquid crystal aligning agent, liquid crystal aligning film and liquid crystal display element
  • Liquid crystal aligning agent, liquid crystal aligning film and liquid crystal display element
  • Liquid crystal aligning agent, liquid crystal aligning film and liquid crystal display element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0136] (Example 1) Synthesis of DA-1

[0137] [chemical 11]

[0138]

Synthetic example 1）

[0139] (Synthesis Example 1) Synthesis of DA-1-1, a precursor of DA-1

[0140] [chemical 12]

[0141]

[0142] Add 56.8g of 2,4-dinitrofluorobenzene, 300mL of toluene, 137.0g of 1,4-butanediol and 37.0g of triethylamine into a 500mL three-neck flask, heat the system to 100°C and stir. After the reaction, 1N hydrochloric acid was added to adjust the pH to 6-7. The organic layer was extracted with ethyl acetate, and anhydrous magnesium sulfate was added to the organic layer for dehydration and drying. After filtration, the solvent was distilled off with a rotary evaporator to obtain 69.9 g of the target object (yellow viscous body) (yield 89%). Target 1 The H-NMR measurement results are shown below. From the above results, it was confirmed that the obtained solid was the target object DA-1-1. 1 H-NMR refers to the nuclear magnetic resonance spectrum of hydrogen atoms in molecules.

[0143] 1 H NMR (400MHz, [D 6 ]-DMSO): δ8.75-8.76(d,1H),8.48-8.51(d,2H),7.57(s,1H),4.33-...

Synthetic example 2）

[0144] (Synthesis Example 2) Synthesis of DA-1-2, a precursor of DA-1

[0145] [chemical 13]

[0146]

[0147] Add 38.43 g of DA-1-1, 350 mL of methylene chloride, 20.6 g of methanesulfonyl chloride, and 37.9 g of triethylamine into a 500 mL three-necked flask, and stir at room temperature. After the reaction was finished, extract the organic layer with ethyl acetate, add anhydrous magnesium sulfate to the organic layer for dehydration and drying, after filtering, remove the solvent by distillation with a rotary evaporator to obtain 48.8g of the target object (orange viscous body) (yield 97%). Target 1 The H-NMR measurement results are shown below. From the above results, it was confirmed that the obtained solid was the target object DA-1-2.

[0148] 1 H NMR (400MHz, [D 6 ]-DMSO): δ8.75-8.77(d,1H),8.48-8.52(d,1H),7.57-7.60(d,1H),4.25-4.40(m,4H),3.18-3.19(t,3H ),1.84-1.89(m,4H)

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Abstract

Disclosed are: a material for a liquid crystal alignment film, which does not undergo film detachment or scratching during rubbing even when the material is burned at a temperature of 200°C or lower and can achieve good liquid crystal alignment properties; and a novel diamine which is used in the material. Specifically disclosed is a liquid crystal aligning agent comprising at least one polymer selected from the group consisting of a polyamic acid and a polyimide produced by dehydrating and ring-closing the polyamic acid, wherein a diamine component comprises a diamine represented by formula [3]. (In the formula, R3 represents a group selected from the group consisting of -CH2-, -O-, -CONH-, -NHCO-, -COO-, -OCO- and -NH-; R4 represents a single bond or an alkylene group having 1-10 carbon atoms; R5 represents a single bond, -CH2-, -O- or -NH-; R6 represents a bivalent organic group which is composed of one or several rings, has at last one aromatic ring at an terminal thereof, and has 5-18 carbon atoms; and R7 represents a hydrogen atom, a methyl group or the like.)

Description

technical field [0001] This invention relates to the liquid crystal aligning agent used at the time of manufacture of a liquid crystal aligning film, the liquid crystal aligning film obtained from this liquid crystal aligning agent, the liquid crystal display element which has this liquid crystal aligning film, and novel diamine suitable for these. Background technique [0002] For liquid crystal display elements used in liquid crystal televisions, liquid crystal monitors, and liquid crystal displays of portable devices, most polyamide-based liquid crystal aligning films are used because they are excellent in productivity, chemical durability, and thermal durability. The polyimide-based liquid crystal alignment film is usually fired at a temperature of about 200 to 250° C. by coating a solution of polyimide or a solution of polyamic acid as a precursor of polyimide on a substrate. to make. [0003] The firing process when producing polyimide-based liquid crystal alignment f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G02F1/1337C07C217/84C07C229/60C08G73/10
CPCC07C229/60G02F1/133723C07C217/84C08G73/10G02F1/1337
Inventor 森内正人
Owner NISSAN CHEM CORP