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Benzofuran liquid crystal compound with difluoromethyl ether bridge and composition thereof

A liquid crystal compound, benzofuran technology, applied in the field of liquid crystal displays, benzofuran liquid crystal compounds, to achieve the effect of improving dielectric anisotropy, high-definition bright spots, and good light/thermal stability

Active Publication Date: 2021-08-20
XIAN MODERN CHEM RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patents CN108003895A and DE102004053279A1 respectively disclose liquid crystal materials with 5,6-difluoro and 5,6,7-trifluoro-substituted benzofuran rings, but the dielectric anisotropy of these materials is still at a moderate level

Method used

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  • Benzofuran liquid crystal compound with difluoromethyl ether bridge and composition thereof
  • Benzofuran liquid crystal compound with difluoromethyl ether bridge and composition thereof
  • Benzofuran liquid crystal compound with difluoromethyl ether bridge and composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0119] 2-(4-((3,5-difluoro-4'-propyl-4-biphenyl)difluoromethoxy)-2,6-difluorophenyl)-5,6-difluorobenzene Synthesis of furans

[0120] The specific structure is as follows:

[0121]

[0122] The preparation process is as follows:

[0123] (1) Synthesis of intermediate 4‐(difluoromethyl bromide)‐3,5‐difluoro‐4'‐propyl‐1,1'‐biphenyl

[0124]

[0125] Under the protection of nitrogen, add 3,5-difluoro-4'-propyl-1,1' to a 250mL three-neck round bottom flask equipped with mechanical stirring, thermometer, constant pressure dropping funnel, reflux condenser, and nitrogen air tube. - biphenyl (34.8g, 0.15mol), dry THF (250mL), liquid nitrogen cooled to -78 ° C, began to drop n-butyllithium (79.1mL, 0.19mol, 2.4M n-hexane solution), dropwise After the incubation reaction for 1 hour, add the pre-frozen THF (50mL) solution dissolved in difluorodibromomethane (63g, 0.3mol) dropwise, continue the incubation reaction for 1.5 hours after the drop, gradually rise to room temperature ...

Embodiment 2

[0151] Synthesis of 2-(4-((2,6-difluoro-4-propylphenyl)difluoromethoxy)-2,6-difluorophenyl)-5,6-difluorobenzofuran

[0152] The specific structure is as follows:

[0153]

[0154] The preparation process is as follows:

[0155] (1) Synthesis of intermediate 2-(difluorobromomethyl)-1,3-difluoro-5-propylbenzene

[0156]

[0157] Using 1,3-difluoro-5-propylbenzene to replace the intermediate 4-(difluoromethyl bromide)-3,5-difluoro-4'-propyl-1,1'-biphenyl in Example 1 3,5-difluoro-4'-propyl-1,1'-biphenyl in the step, the compound 2-(difluorobromomethyl)-1,3-difluoro-5- Propylbenzene.

[0158] (2) Synthesis of intermediate 4-(5,6-difluorobenzofuran-2-yl)-3,5-difluorophenol

[0159] Experiment with embodiment 1.

[0160] (3) The target compound 2-(4-((2,6-difluoro-4-propylphenyl)difluoromethoxy)-2,6-difluorophenyl)-5,6-difluorobenzene Synthesis of furans

[0161]

[0162] Using 2-(difluorobromomethyl)-1,3-difluoro-5-propylbenzene instead of Example 1 compound 2-(4-((...

Embodiment 3

[0167] 2-(4-((2,6-difluoro-4-(4-propylcyclohexyl)phenyl)difluoromethoxy)-2,6-difluorophenyl)-5,6-difluoro Synthesis of Benzofuran

[0168] The specific structure is as follows:

[0169]

[0170] The preparation process is as follows:

[0171] (1) Synthesis of intermediate 2-(difluorobromomethyl)-1,3-difluoro-5-(4-propylcyclohexyl)benzene

[0172]

[0173] Using 1,3-difluoro-5-(4-propylcyclohexyl)benzene to replace the intermediate 4-(difluoromethyl bromide)-3,5-difluoro-4'-propyl-1 in Example 1, 3,5-difluoro-4'-propyl-1,1'-biphenyl in the 1'-biphenyl synthesis step, the compound 2-(difluorobromomethyl)-1,3 -Difluoro-5-(4-propylcyclohexyl)benzene.

[0174] (2) Synthesis of intermediate 4-(5,6-difluorobenzofuran-2-yl)-3,5-difluorophenol

[0175] Experiment with embodiment 1.

[0176] (3) The target compound 2-(4-((2,6-difluoro-4-(4-propylcyclohexyl)phenyl)difluoromethoxy)-2,6-difluorophenyl)-5 , Synthesis of 6-Difluorobenzofuran

[0177]

[0178] Using 2-(difluoro...

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Abstract

The invention discloses a benzofuran liquid crystal compound with a difluoromethyl ether bridge, the general structural formula of which is shown in (1): wherein, R 1 It is a straight-chain alkyl, alkenyl or alkoxy group with 1 to 9 carbons; ring A is a benzene ring, trans-cyclohexane, and the hydrogen atoms on the benzene ring can be replaced by one or more fluorine atoms; n = 0 or 1; x 1 ~X 5 is a hydrogen atom or a fluorine atom; and compositions containing the compound. The liquid crystal compound of the present invention has the characteristics of large dielectric anisotropy and high birefringence, and is suitable for TFT liquid crystal display, especially IPS, FFS, TN and VA display modes.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal materials, in particular to a benzofuran liquid crystal compound with difluoromethyl ether bridges, which is mainly used in liquid crystal displays. Background technique [0002] A liquid crystal display uses the properties of optical anisotropy and dielectric anisotropy of liquid crystal materials to realize display functions. According to its display mode, it can be divided into twisted nematic (TN), super twisted nematic (STN), super twisted nematic (STN), dynamic scattering mode (DSP), thin film transistor driving mode (TFT) and so on. TFT liquid crystal display can realize full color, high resolution, wide viewing angle, fast response, etc., and has been widely used. [0003] Liquid crystal material is the key optoelectronic material of liquid crystal display, which has a very important influence on the performance of the display. In practical applications, since any single component...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K19/34C09K19/44
CPCC09K19/3405C09K19/44C09K2019/3408
Inventor 杨晓哲李建李娟利车昭毅莫玲超万丹阳胡明刚安忠维杨诚张璐史凤娇
Owner XIAN MODERN CHEM RES INST
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