Tetracyclic liquid crystalline compound having two atom-bonded group and 2,3-difluorophenylene, liquid crystal composition and liquid crystal display element

A compound and phenylene technology, applied in the field of liquid crystal display elements, can solve problems such as unclear performance of liquid crystals, and achieve the effects of short response time, wide temperature range, and large contrast ratio

Active Publication Date: 2018-08-31
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0025] Compounds (A)~Compounds (J) have been disclosed, but the properties of liquid crystals are unknown

Method used

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  • Tetracyclic liquid crystalline compound having two atom-bonded group and 2,3-difluorophenylene, liquid crystal composition and liquid crystal display element
  • Tetracyclic liquid crystalline compound having two atom-bonded group and 2,3-difluorophenylene, liquid crystal composition and liquid crystal display element
  • Tetracyclic liquid crystalline compound having two atom-bonded group and 2,3-difluorophenylene, liquid crystal composition and liquid crystal display element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0238] 1. Examples of compound (1)

[0239] 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 compounds were 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.

[0240] NMR analysis: For measurement, DRX-500 manufactured by Bruker BioSpin was used. 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 accumulati...

Synthetic example 1

[0274] Synthesis of Compound (No.121)

[0275]

[0276] Step 1:

[0277] The tetrahydrofuran (Tetrahydrofuran, THF) (100mL) solution of the compound (T-2) (15.5g, 27.5mmol) synthesized by a known method was cooled to -60°C, and potassium tert-butoxide (3.08g, 27.5mmol) was added dropwise. ), and stirred for 1 hour. Thereto, a THF (100 mL) solution of compound (T-1) (6.7 g, 25 mmol) synthesized by a known method was added dropwise, and the mixture was returned to room temperature while stirring. The reaction mixture was poured into water, subjected to usual post-treatment, and purified by silica gel chromatography. Solmix A-11 (100 mL), toluene (50 mL) and 6N hydrochloric acid (20 mL) were added to the purified product (8.3 g, 17.6 mmol; 70%), and heated to reflux for 4 days. It purified by column chromatography and recrystallization after usual post-processing, and obtained compound (No. 121) (4.6 g, 9.75 mmol; 55%).

[0278] 1 H-NMR (CDCl 3 ;δppm): 6.84(1H,dt,7.5Hz,2...

Synthetic example 2

[0281] Synthesis of Compound (No.122)

[0282]

[0283] Step 1:

[0284] (Methoxymethyl)triphenylphosphonium chloride (482.08g, 1.41mol) in THF (2L) was cooled to -60°C, potassium tert-butoxide (215.66g, 1.92mol) was added dropwise, and stirred for 1 Hour. Thereto, a THF (900 mL) solution of compound (T-3) (300.67 g, 1.26 mol) synthesized by a known method was added dropwise, and the mixture was returned to room temperature while stirring. The reaction mixture was poured into water, subjected to usual post-treatment, and purified by silica gel chromatography to obtain compound (T-4) (293.17 g, 1.10 mol; 87%).

[0285] Step 2:

[0286] Add 6N hydrochloric acid (180mL, 1.08mol) dropwise to compound (T-4) (293.17g, 1.10mol) and 2,2-dimethyl-1,3-propanediol (125.71g, 1.21mol) in acetone solution , and stirred at room temperature for several days. The usual post-treatment was carried out, followed by purification by silica gel chromatography and recrystallization to obtain ...

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Abstract

The means according to the present invention are: a compound represented by formula (1); a liquid crystal composition containing this compound; and a liquid crystal display element comprising this composition. In formula (1), each of R1 and R2 independently represents an alkyl group having 1-15 carbon atoms or the like; each of ring A1, ring A2 and ring A3 independently represents 1,4-cyclohexylene, 1,4-phenylene or the like; and each of Z1, Z2 and Z3 independently represents a single bond or the like.

Description

technical field [0001] The present 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 2,3-difluorophenylene and negative dielectric constant anisotropy, a liquid crystal composition containing it, and a liquid crystal display element containing the composition . Background technique [0002] In liquid crystal display elements, the classification based on the action mode of liquid crystal molecules is phase change (phase change, PC), twisted nematic (twisted nematic, TN), super twisted nematic (super twisted nematic, STN), electrically controlled birefringence (electrically controlled birefringence, ECB), optically compensated bend (OCB), in-plane switching (IPS), vertical alignment (vertical alignment, VA), fringe field switching (fringe field switching, FFS), electric field Sensing photoreactive alignment (field-induced photo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C07D309/06C09K19/12C09K19/14C09K19/18C09K19/20C09K19/30C09K19/32C09K19/34C09K19/42G02F1/13
CPCC07D309/06C07C43/225C09K19/12C09K19/14C09K19/18C09K19/20C09K19/30C09K19/42G02F1/13C09K19/3028C09K19/3048C09K19/3066C09K19/3068C09K19/3402C09K2019/0466C09K2019/123C09K2019/181C09K2019/3004C09K2019/3009C09K2019/301C09K2019/3016C09K2019/3019C09K2019/3027C09K2019/3042C09K2019/3422C09K2019/3039C09K19/32
Inventor 森绚子木村敬二佐藤祯治
Owner JNC CORP
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