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Compound having dibenzofuran ring, liquid crystal composition, and liquid crystal display element

A compound and group technology, used in organic chemistry, liquid crystal materials, chemical instruments and methods, etc., can solve problems such as insufficient compatibility, and achieve the effects of short response time, wide temperature range, and low threshold voltage

Active Publication Date: 2019-10-01
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compound has a large dielectric anisotropy, but the compatibility at low temperature is not sufficient

Method used

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  • Compound having dibenzofuran ring, liquid crystal composition, and liquid crystal display element
  • Compound having dibenzofuran ring, liquid crystal composition, and liquid crystal display element
  • Compound having dibenzofuran ring, liquid crystal composition, and liquid crystal display element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0245] 1. Examples of compound (1)

[0246] The present invention is illustrated in more detail by way of examples. The Examples are typical examples, and therefore the present invention is not limited by the Examples. Compound (1) was synthesized by the following procedure. The synthesized compound was identified by nuclear magnetic resonance (Nuclear Magnetic Resonance, NMR) analysis and other methods. The physical properties of the compound or composition, and the characteristics of the device were measured by the following methods.

[0247] NMR analysis: DRX-500 manufactured by Bruker BioSpin was used for measurement. exist 1 In the measurement of H-NMR, the sample is dissolved in CDCl 3 and other deuterated solvents, and measured at room temperature, 500 MHz, and accumulated times 16 times. Tetramethylsilane was used as an internal standard. exist 19 In the determination of F-NMR, the CFCl 3 It was used as an internal standard, and it carried out by accumulating ...

Synthetic example 1

[0286] Synthesis of Compound (No.26)

[0287]

[0288] Step 1: Synthesis of compound (T-2)

[0289] Under nitrogen atmosphere, compound (T-1) (16.0g), cyclopentylmethanol (8.39g), triphenylphosphine (26.4g), and tetrahydrofuran (Tetrahydrofuran, THF) (150mL) are put into reactor , cooled on an ice bath. Diethyl azodicarboxylate (DEAD (azodicarboxylic acid diethyl), 2.2M; toluene solution; 45.7 ml) was added, and stirred at room temperature for 8 hours. After the reaction, the reaction mixture was poured into water, and the water layer was extracted with toluene. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Compound (T-2) (19.8 g; 86%) was obtained by purifying the residue by silica gel chromatography (volume ratio, toluene:heptane=1:4).

[0290] Step 2: Synthesis of compound (T-3)

[0291]Under a nitrogen atmosphere, compound (T-2) (19.8 g) and tetrahydrofuran (THF, 200 mL) were put...

Synthetic example 2

[0299] Synthesis of compound (No.3)

[0300]

[0301] Step 1: Synthesis of compound (T-7)

[0302] Under a nitrogen atmosphere, compound (T-6) (60.0 g) and tetrahydrofuran (500 ml) were put into a reactor, and cooled to -70°C. Thereto, n-butyl lithium (1.64M; n-hexane solution; 127.7 ml) was slowly added, followed by stirring for 1 hour. Then, a solution of cyclopentanone (17.6 g) in tetrahydrofuran (50.0 ml) was slowly added, and the mixture was returned to room temperature and stirred for 12 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with toluene. The mixed organic layers were washed with brine, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and purified by silica gel chromatography (volume ratio, ethyl acetate:heptane=1:8), thereby obtaining Compound (T-7) (31.9 g; 57%).

[0303] Step 2: Synthesis of compound (T-8)

[0304] Under a nitrogen atmosphere, compound (T-7) (31.9...

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Abstract

The purpose of the present invention is to provide a liquid crystalline compound; a liquid crystal composition containing the compound; and a liquid crystal display element including the composition,the liquid crystalline compound satisfying at least one physical property among high stability against heat and light, high transparency, low minimum temperature of the liquid crystal phase, low viscosity, proper optical anisotropy, negatively large dielectric anisotropy, proper elastic constant, good compatibility with other liquid crystalline compounds at room temperature and low temperature, and the like. Provided is a compound represented by formula (1), or the like. In the formula, R1 and R2 are hydrogen, C1-10 alkyl, C2-9 alkoxyl, or the like; ring A1 is 1,3-cyclopentylene or the like; Y1 and Y2 are hydrogen, fluorine, or the like; Z1 and Z2 are a single bond, C1-6 alkylene, or the like; ring N1 is 1,4-cyclohexylene, 1,4-penylene, or the like; and n is 0, 1, or 2.

Description

technical field [0001] The invention relates to a liquid crystal compound, a liquid crystal composition and a liquid crystal display element. More specifically, the present invention relates to a liquid crystal compound having a dibenzofuran ring and having a negative dielectric anisotropy, a liquid crystal composition containing the same, and a liquid crystal display device containing the composition. Background technique [0002] In liquid crystal display elements, the classification based on the operation mode of liquid crystal molecules is phase change (phase change, PC), twisted nematic (twisted nematic, TN), super twisted nematic (super twisted nematic, STN), electronically controlled birefringence ( Electrically controlled birefringence (ECB), optically compensated bend (OCB), in-plane switching (IPS), vertical alignment (vertical alignment, VA), fringe field switching (FFS), electric field sensing Field-induced photo-reactive alignment (FPA) and other modes. The co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/91C07D407/04C09K19/12C09K19/18C09K19/20C09K19/30C09K19/32C09K19/34C09K19/42G02F1/13
CPCC07D407/04C07D307/91C09K19/12C09K19/18C09K19/20C09K19/30C09K19/32C09K19/34C09K19/3405C09K19/42G02F1/13C09K2019/3408C09K2019/3009C09K2019/181C09K2019/301C09K2019/3077C09K2019/3004C09K2019/3016C09K2019/3021C09K2019/3019C09K2019/3042C09K19/3028C09K2019/304C09K2019/308C09K2019/3083C09K2019/3422C09K19/3059C09K2019/0466C09K2019/123C09K2019/122C09K2019/3071C09K2019/3425
Inventor 高田章博
Owner JNC CORP
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