Liquid crystal aligning agent containing crosslinkable compound having photoreactive group

A liquid crystal aligning agent and cross-linking technology, which is applied in the field of liquid crystal display elements, and can solve the problems of low solubility of photopolymerizable compounds and precipitation of addition amount.

Active Publication Date: 2018-02-06
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the liquid crystal display element of the PSA method has the following problems: the solubility of the photopolymerizable compound added to the liquid crystal is low, and when the addition amount is increased, it will precipitate at low temperature
However, the low solubility of the photopolymerizable compound in the liquid crystal aligning agent is a problem

Method used

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  • Liquid crystal aligning agent containing crosslinkable compound having photoreactive group
  • Liquid crystal aligning agent containing crosslinkable compound having photoreactive group
  • Liquid crystal aligning agent containing crosslinkable compound having photoreactive group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0256] Although Examples and Comparative Examples are given below and the present invention will be described in more detail, the explanation of the present invention is not limited to these Examples. It should be noted that the abbreviations in the examples are as follows.

[0257]

[0258]

[0259] RM: 5,5-(biphenyl-4,4'-diylbis(oxygen))bis(pentane-5,1-diyl)bis(2-methacrylate)

[0260]

[0261] BODA: Bicyclo[3,3,0]octane-2,4,6,8-tetracarboxylic dianhydride

[0262] CBDA: 1,2,3,4-cyclobutanetetracarboxylic dianhydride

[0263] TCA: 2,3,5-Tricarboxycyclopentylacetic dianhydride

[0264]

[0265] PCH: 1,3-diamino-3-[4-(4-heptylcyclohexyl)phenoxy]benzene

[0266] DA-Col: Cholesteryl 3,5-diaminobenzoate

[0267] DBA: 3,5-diaminobenzoic acid

[0268] DA-1: 2-(methacryloyloxy)ethyl-3,5-diaminobenzoate

[0269] DA-2: N 1 ,N 1 -Diarylbenzene-1,2,4-triamine

[0270]

[0271] 3-AMP: 3-pyridylmethylamine

[0272] (NMP: N-methyl-2-pyrrolidone

[0273] BCS: Butyl...

Synthetic example 1

[0283] (Synthesis Example 1) Synthesis of CL-1

[0284] (Step 1) Synthesis of CL-1-1, the precursor of CL-1

[0285]

[0286] 10.9 g of 3,3',5,5'-tetrakis(methoxymethyl)-[1,1'-biphenyl]-4,4'-diol, 200 mL of DMF, 12.3 g of 6-chloro-1-hexanol, 24.9 g of potassium carbonate, and 2.5 g of potassium iodide were stirred while heating to 100°C. After the reaction, the reaction system was poured into 1 L of water, neutralized with 1N-hydrochloric acid (HCl) aqueous solution, and the precipitate was filtered. This filtrate was dried to obtain 16.9 g of CL-1-1 (yellow solid) (99% yield).

[0287] (Step 2) Synthesis of CL-1 from precursors

[0288]

[0289] CL-1-116.9 g, 7.30 g of triethylamine, and 160 mL of THF were added to a 300 mL four-necked flask. The inside of the system was cooled to 0° C., 7.30 g of methacryloyl chloride was added, and stirred at room temperature (rt: 25° C.). After completion of the reaction, the reaction system was poured into 500 mL of water, and ...

Synthetic example 2

[0292] (Synthesis Example 2) Synthesis of CL-2

[0293] (Step 1) Synthesis of CL-2-1, the precursor of CL-2

[0294]

[0295]17.8 g of trans-methyl p-coumarate, 250 mL of DMF, 20.5 g of 6-chloro-1-hexanol, 41.5 g of potassium carbonate, and 1.7 g of potassium iodide were added to a 500 mL three-necked flask, and stirred at 100°C. After the reaction, the reaction system was poured into 1.2 L of water, neutralized with 1N-hydrochloric acid (HCl) aqueous solution, and the precipitate was filtered. The filtrate was dissolved in 300 mL of ethyl acetate, extracted with saturated brine, dehydrated and dried by adding anhydrous magnesium sulfate to the organic layer, filtered, and the solvent was distilled off using a rotary evaporator to obtain 25.6 g of the target compound CL -2-1 (white solid) (92% yield).

[0296] (Step 2) Synthesis of CL-2-2, the precursor of CL-2

[0297]

[0298] 25.6 g of CL-2-1, 200 mL of THF, and 11.2 g of triethylamine were added to a 500 mL three-...

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Abstract

Provided is a liquid crystal aligning agent which exhibits excellent storage stability during refrigerated storage by using a crosslinkable compound that comprises a photoreactive group and has high solubility in liquid crystal aligning agents. This liquid crystal aligning agent is capable of improving the response speed of a liquid crystal display element which comprises a liquid crystal alignment film that is formed from this liquid crystal aligning agent. A liquid crystal aligning agent which contains a crosslinkable compound represented by formula [1] wherein two or more polymerizable groups (Py1, Py2) and ten or less crosslinkable groups (CL1, CL2) are bonded to a parent nucleus that is composed of a divalent or higher-valent organic group. (In formula [1], L-M-R represents a parent nucleus; each of L and R represents a carbon ring or heterocyclic ring having 4-12 carbon atoms; M represents a single bond or the like; each of S1, S2, S3 and S4 represents a single bond or the like; each of l, o, n and m represents an integer of 1 or more; n + m is 10 or less; and l + o is 10 or less.)

Description

technical field [0001] The present invention relates to a liquid crystal aligning agent containing a cross-linking compound into which a structure photopolymerized by ultraviolet (UV) irradiation (photoreactive group). Background technique [0002] In recent years, among the display methods of liquid crystal display elements, vertical alignment type (VA method) liquid crystal display elements have been widely used in large-screen liquid crystal televisions, high-definition mobile applications (digital cameras, display parts of mobile phones), and the like. Known in the VA method are: the MVA method (MultiVertical Alignment, wide-area vertical alignment) in which protrusions for controlling the liquid crystal tilting direction are formed on the TFT substrate and the color filter substrate; the slit is formed on the ITO electrode of the substrate and used The PVA (Patterned Vertical Alignment) method in which the electric field controls the tilting direction of the liquid cry...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G02F1/1337C07C43/215C07C69/736C08F12/34C08F20/30C08K5/06C08K5/10C08L79/08C08L83/04
CPCC08F12/22C08F12/32C08F12/34C08G77/20C08K5/10C08L83/04C09K19/20C09K2019/0448G02F1/133711
Inventor 森内正人芦泽亮一桥本淳后藤耕平
Owner NISSAN CHEM IND LTD
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