Side difluorine substituted diphenylacetylene liquid crystal compound, preparation method for same and application thereof

Abstract

The invention discloses a side difluorine substituted diphenylacetylene liquid crystal compound, a preparation method for the same and application thereof. The compound is represented by the structural general formula I. The liquid crystal molecule performance is improved by introducing fluorine atoms into a molecular structure, increasing the molecular width and the fluorine atom number, decreasing the melting point and enhancing intermiscibility, and a molecular shape is transformed by leading two rodlike molecules including side difluorines to be in acetylenic bond linkage, so that the Z-shaped compound is formed. The side fluorine atom substituted liquid crystal compound is high in resistivity, has high dielectric anisotropy, is capable of meeting the requirement of a VA-TFT mode, and can be used as liquid crystal display materials and liquid crystal monomers. (Formula I).

Description

technical field

[0001] The invention relates to a lateral difluoro-substituted tolanyl liquid crystal compound and its preparation method and application. Background technique

[0002] Liquid crystal materials are developed rapidly along with the development of liquid crystal displays. Among them, the nematic liquid crystals used for display are the fastest-growing type of liquid crystal materials. Nematic liquid crystal materials have many types such as TN type, STN type, and TFT type. a display mode. With the development of electronic information technology, people have higher requirements for the response speed and image quality of the display, which puts forward higher performance requirements for liquid crystal materials.

[0003] According to the use requirements of display devices, liquid crystal compounds should meet the following performance requirements:

[0004] Liquid crystal material has light, heat and electrical stability;

[0005] Has a wide nematic phase ...

Examples

Embodiment 1

[0082] Embodiment 1 compound formula I-1 (R 1 =C 2 h 5 , R 2 =C 2 h 5 ) preparation

[0083]

[0084] (Formula I-1)

[0085] Step 1: Preparation of 5-(4-(4'-ethylcyclohexyl)cyclohexyl)-2,3-difluoroiodobenzene

[0086]

[0087] In the 1000ml reaction bottle, drop into 0.10mol 5-(4-(4'-ethylcyclohexyl)cyclohexyl)-1,2-difluorobenzene, drop into 300ml THF, under N 2 Under protection, use a liquid nitrogen / ethanol bath to lower the temperature of the system below -80°C, add 0.15 moln-BuLi hexane solution dropwise, and keep it below -80°C to react for 1 hour after dropping. Maintain the temperature, and add dropwise a THF solution containing 0.15 mol of iodine. After the dropwise addition, keep the temperature for reaction for 1 hour, and then gradually rise to room temperature for reaction for 2 hours. Then add 100ml saturated aqueous sodium thiosulfate solution, separate the organic phase, wash 3 times with 30ml saturated brine, dry the organic phase with anhydrous s...

Embodiment 2

[0102] Embodiment 2 compound formula I-3 (R 1 =C 3 h 7 , R 2 =C 5 h 11 ) preparation

[0103]

[0104] (Formula I-3)

[0105] Step 1: Preparation of 5-(4-(4'-propylcyclohexyl)cyclohexyl)-2,3-difluoroiodobenzene

[0106] In the 1000ml reaction bottle, drop into 0.10mol 5-(4-(4'-propylcyclohexyl)cyclohexyl)-1,2-difluorobenzene, drop into 300ml THF, under N 2 Under protection, use a liquid nitrogen / ethanol bath to lower the temperature of the system below -80°C, add 0.15 moln-BuLi hexane solution dropwise, and keep it below -80°C to react for 1 hour after dropping. Maintain the temperature, and add dropwise a THF solution containing 0.15 mol of iodine. After the dropwise addition, keep the temperature for reaction for 1 hour, and then gradually rise to room temperature for reaction for 2 hours. Then add 100ml saturated aqueous sodium thiosulfate solution, separate the organic phase, wash 3 times with 30ml saturated brine, dry the organic phase with anhydrous sodium sul...

Embodiment 3

[0121] Embodiment 3 compound formula I-14 (R 1 =C 3 h 7 , R 2 =C 3 h 7 ) preparation

[0122]

[0123] (Formula I-14)

[0124] Step 1: Preparation of 2,3,3',4'-tetrafluoro-5'-iodo-4-propylbiphenyl

[0125] In the 1000ml reaction flask, drop into 0.10mol 2,3,3',4'-tetrafluoro-4-propyl biphenyl and 300ml THF, in N 2 Under protection, use a liquid nitrogen / ethanol bath to lower the temperature of the system below -80°C, add 0.15mol n-BuLi in hexane dropwise, and keep the temperature below -80°C to react for 1 hour after dropping. Maintain the temperature, and add dropwise a THF solution containing 0.15 mol of iodine. After the dropwise addition, keep the temperature for reaction for 1 hour, and then gradually rise to room temperature for reaction for 2 hours. Then add 100ml of saturated aqueous sodium thiosulfate solution, separate the organic phase, wash 3 times with 50ml of saturated brine, dry the organic phase with anhydrous sodium sulfate, and spin dry under reduc...

technical field

[0001] The invention relates to a lateral difluoro-substituted tolanyl liquid crystal compound and its preparation method and application. Background technique

[0002] Liquid crystal materials are developed rapidly along with the development of liquid crystal displays. Among them, the nematic liquid crystals used for display are the fastest-growing type of liquid crystal materials. Nematic liquid crystal materials have many types such as TN type, STN type, and TFT type. a display mode. With the development of electronic information technology, people have higher requirements for the response speed and image quality of the display, which puts forward higher performance requirements for liquid crystal materials.

[0003] According to the use requirements of display devices, liquid crystal compounds should meet the following performance requirements:

[0004] Liquid crystal material has light, heat and electrical stability;

[0005] Has a wide nematic phase ...

Examples

Embodiment 1

[0082] Embodiment 1 compound formula I-1 (R 1 =C 2 h 5 , R 2 =C 2 h 5 ) preparation

[0083]

[0084] (Formula I-1)

[0085] Step 1: Preparation of 5-(4-(4'-ethylcyclohexyl)cyclohexyl)-2,3-difluoroiodobenzene

[0086]

[0087] In the 1000ml reaction bottle, drop into 0.10mol 5-(4-(4'-ethylcyclohexyl)cyclohexyl)-1,2-difluorobenzene, drop into 300ml THF, under N 2 Under protection, use a liquid nitrogen / ethanol bath to lower the temperature of the system below -80°C, add 0.15 moln-BuLi hexane solution dropwise, and keep it below -80°C to react for 1 hour after dropping. Maintain the temperature, and add dropwise a THF solution containing 0.15 mol of iodine. After the dropwise addition, keep the temperature for reaction for 1 hour, and then gradually rise to room temperature for reaction for 2 hours. Then add 100ml saturated aqueous sodium thiosulfate solution, separate the organic phase, wash 3 times with 30ml saturated brine, dry the organic phase with anhydrous s...

Embodiment 2

[0102] Embodiment 2 compound formula I-3 (R 1 =C 3 h 7 , R 2 =C 5 h 11 ) preparation

[0103]

[0104] (Formula I-3)

[0105] Step 1: Preparation of 5-(4-(4'-propylcyclohexyl)cyclohexyl)-2,3-difluoroiodobenzene

[0106] In the 1000ml reaction bottle, drop into 0.10mol 5-(4-(4'-propylcyclohexyl)cyclohexyl)-1,2-difluorobenzene, drop into 300ml THF, under N 2 Under protection, use a liquid nitrogen / ethanol bath to lower the temperature of the system below -80°C, add 0.15 moln-BuLi hexane solution dropwise, and keep it below -80°C to react for 1 hour after dropping. Maintain the temperature, and add dropwise a THF solution containing 0.15 mol of iodine. After the dropwise addition, keep the temperature for reaction for 1 hour, and then gradually rise to room temperature for reaction for 2 hours. Then add 100ml saturated aqueous sodium thiosulfate solution, separate the organic phase, wash 3 times with 30ml saturated brine, dry the organic phase with anhydrous sodium sul...

Embodiment 3

[0121] Embodiment 3 compound formula I-14 (R 1 =C 3 h 7 , R 2 =C 3 h 7 ) preparation

[0122]

[0123] (Formula I-14)

[0124] Step 1: Preparation of 2,3,3',4'-tetrafluoro-5'-iodo-4-propylbiphenyl

[0125] In the 1000ml reaction flask, drop into 0.10mol 2,3,3',4'-tetrafluoro-4-propyl biphenyl and 300ml THF, in N 2 Under protection, use a liquid nitrogen / ethanol bath to lower the temperature of the system below -80°C, add 0.15mol n-BuLi in hexane dropwise, and keep the temperature below -80°C to react for 1 hour after dropping. Maintain the temperature, and add dropwise a THF solution containing 0.15 mol of iodine. After the dropwise addition, keep the temperature for reaction for 1 hour, and then gradually rise to room temperature for reaction for 2 hours. Then add 100ml of saturated aqueous sodium thiosulfate solution, separate the organic phase, wash 3 times with 50ml of saturated brine, dry the organic phase with anhydrous sodium sulfate, and spin dry under reduc...

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