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Novel tetracyclic diene liquid crystal compound and preparation method thereof

A technology of liquid crystal compound and tetracyclic diene, which is applied in the field of new tetracyclic diene liquid crystal compound and its preparation, can solve problems such as small dielectric anisotropy value, improve steepness and viewing angle, avoid side reactions, design reasonable effect

Active Publication Date: 2013-02-20
HEBEI MAIERSTON ELECTRONICS MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although this type of compound has high resistivity and good stability, but the dielectric anisotropy value is small

Method used

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  • Novel tetracyclic diene liquid crystal compound and preparation method thereof
  • Novel tetracyclic diene liquid crystal compound and preparation method thereof
  • Novel tetracyclic diene liquid crystal compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052]Preparation of Example 14-(2-(4-(3,4-difluorophenyl)cyclohexyl)vinyl)-4'-ethylene bicyclohexane

[0053]

[0054] 3,4-difluorophenyl cyclohexyl ketone 80g, according to 3,4-difluorophenyl cyclohexyl ketone: chloromethyl ether phosphine salt: potassium tert-butoxide (mol: mol: mol) = 1: 1.2: 1.5 feeding . Put 300mL tetrahydrofuran solution containing chloromethyl ether phosphonium salt into a 1000mL four-neck flask, cool to below -10°C under nitrogen protection, maintain for 10min, then gradually add potassium tert-butoxide and keep stirring for 30min below 10°C. Add dropwise 3,4-difluorophenylcyclohexyl ketone in 300 mL tetrahydrofuran at below 10°C. After the addition is complete, let it rise to room temperature naturally and react for 4 hours. After the reaction was completed, an appropriate amount of saturated solution of sodium bicarbonate was added until no white precipitate was formed. Separate the liquid, dry the organic phase with anhydrous sodium sulfate ov...

Embodiment 2

[0087] Preparation of Example 24-(2-(4-p-tolylcyclohexyl)vinyl)-4'-ethylene bicyclohexane

[0088] In the process of preparing intermediate I, p-methylphenylcyclohexyl ketone was used as a raw material to react with phosphonium chloromethyl ether to prepare vinyl ether through Wittig reaction, and the rest of the process was the same as that of Example 1. 4-(2-(4-p-tolylcyclohexyl) vinyl)-4'-ethylene bicyclohexane can be obtained, and its structural formula is as follows:

[0089]

[0090] The synthesized compounds were characterized by MS and 1HMR methods to confirm their structures.

[0091]

[0092] MS: m / z: 726.70 (100.0%), 727.71 (58.4%), 728.71 (16.7%), 729.71 (3.0%)

[0093] MP: 190.3°C

[0094] 1 H NMR (CDCl 3 / TMS)δ H : 7.26~6.90(m, 4H, H 1 );5.80~5.73(m,1H,H 2 ); 5.34(t, 2H, H 3 , J=4.4Hz); 4.97~4.86(m, 2H, H 4 ); 2.42(t,1H,H 5 , J=4.9Hz); 2.39(s, 3H, H 9 ); 1.94~1.79(m, 12H, H 7 ); 1.53~1.42(m, 2H, H 5 ); 1.40~1.37(m, 3H, H 6 ); 1.25~1.02(m, 12H, H...

Embodiment 3

[0097] In the same way, use

[0098]

[0099] Used in the process of preparing intermediate I in replacing embodiment 2

[0100]

[0101] Other process is identical with embodiment 2, can finally make:

[0102]

[0103] MP: 199.1°C

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Abstract

The invention relates to a novel tetracyclic diene liquid crystal compound and a preparation method thereof, and the structure of the liquid crystal compound is as follows; wherein R is F, CH3 or CH3O; R1-R4 are H or F; R5 is H or CmH2m+1; and m is 1-15. The preparation method of the novel tetracyclic diene liquid crystal compound is characterized in that an intermediate A (trans-substituted phenyl cyclohexyl methyl iodide triphenyl phosphine salt) and an intermediate B (different substituted vinyl dicyclohexyl formaldehyde) are connected by a Wittig reaction to introduce a double bond in the molecule of a target product, and then a required trans-compound is obtained by double bond translocation.

Description

technical field [0001] The invention relates to a novel tetracyclic diene liquid crystal compound and a preparation method thereof. Background technique [0002] The most widely and most important application of liquid crystal materials is in electronic display - liquid crystal display. Driven by informatization, LCD TVs, notebook computers, mobile phones and other electronic products are becoming more and more popular, and people's requirements for the performance of liquid crystal materials are also increasing. keep improving. The liquid crystal material used for flat panel display is usually made by mixing 5-20 liquid crystal compounds with different characteristics in a certain proportion. Each compound contributes differently to the liquid crystal formula. The mixed liquid crystal composition must satisfy a wide Working temperature range, low working voltage, low viscosity, fast response, good chemical stability, high-definition bright spots, good mutual solubility, hi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/225
CPCY02P20/55
Inventor 仲锡军段二红李洪胜赵地顺张习军王开芳
Owner HEBEI MAIERSTON ELECTRONICS MATERIAL
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