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Novel polymer and diamine compound, liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element

A liquid crystal aligning agent, amine compound technology, applied in optical elements, polarizing elements, organic chemistry, etc., can solve the problems of lower brightness, lower liquid crystal display quality, higher ion density, etc., and achieve high voltage retention and brush abrasion resistance. , indicates the effect of excellent characteristics and high availability

Pending Publication Date: 2019-08-13
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the ion density is high, the voltage applied to the liquid crystal decreases during the frame period, resulting in a decrease in brightness, which sometimes affects normal grayscale representation
In addition, even if the initial ion density is low, there is a problem when the ion density becomes high after a high-temperature accelerated test
The long-term reliability reduction caused by such residual charges and ionic impurities, and the occurrence of image sticking will reduce the quality of liquid crystal display, so it becomes a problem

Method used

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  • Novel polymer and diamine compound, liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element
  • Novel polymer and diamine compound, liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element
  • Novel polymer and diamine compound, liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0188] The present invention will be described in more detail with reference to examples below, but the present invention is not limited thereto. The abbreviations of the compounds used in the present examples and comparative examples and the method of property evaluation are as follows.

[0189] NMP: N-methyl-2-pyrrolidone

[0190] BCS: Butyl Cellosolve

[0191] GBL: gamma-butyrolactone

[0192] DA-1-1: a compound represented by the following formula DA-1-1

[0193] DA-1-2: a compound represented by the following formula DA-1-2

[0194] DA-1-3: a compound represented by the following formula DA-1-3

[0195] DA-1-4: a compound represented by the following formula DA-1-4

[0196] DA-1-5: a compound represented by the following formula DA-1-5

[0197] DA-1-6: a compound represented by the following formula DA-1-6

[0198] DA-1-7: a compound represented by the following formula DA-1-7

[0199] DA-1-8: a compound represented by the following formula DA-1-8

[0200] DA-1-9...

Embodiment A1

[0203] (Embodiment A1: synthesis of specific diamine)

[0204] Synthesis of (DA-1-1)

[0205]

[0206]After adding 8 g (29.8 mmol) of N,N'-(1,4-phenylene) bismaleimide and 160 g of tetrahydrofuran (henceforth THF) to a flask, it cooled with ice. To this mixture was added 9.801 g (65.2 mmol) of 4-(2-methylaminoethyl)aniline. Then, after gradually returning to room temperature, it was stirred at room temperature for 1 day. After confirming the completion of the reaction, THF was distilled off under reduced pressure. 140 g of methanol was added to the obtained residue, followed by stirring. The resulting precipitate was filtered. The filtrate was added to 140 g of methanol, stirred and filtered again to obtain crystals. The obtained crystals were dried at 50° C. to obtain 12.44 g of the target compound (DA-1-1) (yield 73%, HPLC area percentage: 99.1%).

[0207] 1H-NMR (CDCl3, δppm): 7.35 (s, 4H), 6.88 (d, 4H), 6.49 (d, 4H), 4.82 (brs, 4H), 4.19 (dd, 2H), 2.89-2.98 (m, 2...

Embodiment A2

[0208] (Embodiment A2: synthesis of specific diamine)

[0209] Synthesis of (DA-1-2)

[0210]

[0211] 1.00 g (3.73 mmol) of N,N'-(1,4-phenylene) bismaleimide and 10 g of THF were added to the flask, followed by cooling with ice. To this mixture was added 1.00 g (8.19 mmol) of 3-aminomethylaniline. Then, after gradually returning to room temperature, it was stirred at room temperature for 1 day. After confirming the completion of the reaction, THF was distilled off under reduced pressure. Isopropanol (hereinafter referred to as IPA) was added to the obtained residue and stirred to obtain crystals. The obtained crystals were filtered, and the filtered crystals were dried at 50° C. to obtain 0.55 g of the target compound (DA-1-2) (yield 29%).

[0212] 1H-NMR (d6-DMSO, δppm): 7.40(s, 4H), 6.93-6.99(m, 2H), 6.58-6.61(m, 2H), 6.49-6.53(m, 2H), 6.42-6.47(m , 2H), 4.99(brs, 4H), 3.71-3.90(m, 6H), 3.00-3.08(m, 2H), 2.87(brs, 2H), 2.56-2.63(m, 2H)

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PUM

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Abstract

Provided are: a method for producing a diamine compound represented by formula (1), the method comprising a step of reacting the bismaleimide compound represented by formula (A) with either a diaminocompound in which P1 in the compound represented by formula (B) is an amino group, or a nitroamino compound in which P1 in the compound represented by formula (B) is a nitro group; the diamine represented by formula (1); a polymer obtained therefrom; and a liquid crystal alignment agent containing the polymer. [Chemical formula 1] R represents a hydrogen atom or a monovalent organic group, R1 represents a hydrogen atom, or a linear or branched C1-C5 alkyl group or aryl group, the two R1s in the same maleimide ring may be the same as or different from one another, and the two R1s may combine toform a C3-C6 alkylene, W1 represents a single bond or a divalent organic group, W2 represents a divalent organic group, Ar1 represents an aromatic ring, and L1 represents a C1-20 alkylene.

Description

technical field [0001] This invention relates to the novel diamine compound (it abbreviates also diamine in this specification) useful as a raw material of the polymer used for a liquid crystal aligning film, and the polymer obtained using this diamine. More specifically, the present invention relates to, for example, polyimides suitable for use in electronic materials and diamines as raw material monomers thereof. Moreover, this invention relates to the polyamic acid obtained using this diamine, a polyamic acid ester, a polyimide, a liquid crystal aligning agent, a liquid crystal aligning film, and a liquid crystal display element. Background technique [0002] Generally, polyimide resins are widely used as electronic materials such as liquid crystal display elements, protective materials in semiconductors, insulating materials, and color filters due to their high mechanical strength, heat resistance, insulation, and solvent resistance. . In addition, recently, polyimide ...

Claims

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Application Information

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IPC IPC(8): C07D207/416C08G73/10G02F1/1337
CPCC07D207/416C09K19/56G02F1/1337C08G73/10G02B1/111G02B5/30
Inventor 北浩结城达也
Owner NISSAN CHEM IND LTD
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