Dibenzothiophene polymerizable compound and application thereof

Abstract

The invention relates to a dibenzothiophene polymerizable compound and an application thereof. The compound has a structure as shown in a general formula I. Compared with the prior art, the polymerizable liquid crystal compound disclosed by the invention has good solubility and a better alignment effect, the polymerization rate is higher, polymerization is more complete, and the residue amount islower, so that the problem of poor display is improved to a large extent. Furthermore, a liquid crystal composition containing the compound has relatively low viscosity, can realize rapid response andhas moderate dielectric anisotropy delta epsilon. A liquid crystal display element or liquid crystal display comprising the liquid crystal composition has a wide nematic phase temperature range, suitable or relatively high birefringence anisotropy delta n, higher electrical resistivity, good ultraviolet resistance, high charge retention rate, low steam pressure and the like.

Description

technical field

[0001] The invention belongs to the field of liquid crystal compounds and applications thereof, and relates to a dibenzothiophene polymerizable compound and applications thereof. Background technique

[0002] In recent years, liquid crystal display devices have developed more and more rapidly. The application of liquid crystal materials as environmental materials in information display materials, organic optoelectronic materials and other fields has great research value and bright application prospects, and different types have also been developed, such as vehicle-mounted small Liquid crystal display devices, portable liquid crystal display devices, ultra-thin liquid crystal display devices, etc., are making progress in the development of this field. Taking TV as an example, it is characterized by light weight, small space occupation, and easy movement. There are also notebook-type personal computers, Pocket PCs, mobile phones, etc., commercial TFT-LCD produc...

Examples

Embodiment 1

[0058] The structural formula of the liquid crystal compound is:

[0059]

[0060] The synthetic route for preparing compound BYLC-01 is as follows:

[0061]

[0062] Specific steps are as follows:

[0063] (1) Synthesis of compound BYLC-01-1:

[0064] Add 40.5g of 3-benzyloxy-7-bromo-4,6-difluorodibenzothiophene, 20g of diethyl malonate, 14g of potassium tert-butoxide, and 300ml of tetrahydrofuran into the reaction flask, and control the temperature at 50°C to 60°C React at ℃ for 6 hours, lower to room temperature, adjust the pH value to neutral with dilute hydrochloric acid, perform conventional post-treatment, and recrystallize to obtain 43.5 g of light yellow solid (compound BYLC-01-1), HPLC: 99.4%, yield 85.0%;

[0065] (2) Synthesis of compound BYLC-01-2:

[0066] Add 10.0g of aluminum hydride and 500mL of tetrahydrofuran into the reaction flask, cool down to 0°C, control the temperature at 0°C to 10°C, add dropwise a solution composed of 43.5g of compound BYLC-...

Embodiment 2

[0074] The structural formula of the liquid crystal compound is:

[0075]

[0076] The synthetic route for preparing compound BYLC-02 is as follows:

[0077]

[0078] Specific steps are as follows:

[0079] Synthesis of compound BYLC-02:

[0080] Under the protection of nitrogen, add 31.0g of compound BYLC-01-3, 38.4g of triethylamine and 250mL of dichloromethane into the reaction flask, cool down to -10°C, control the temperature from -10°C to 0°C, and add 32.0g of acryloyl chloride dropwise, Rise to room temperature and react for 6 hours. Pour the reaction solution into water, neutralize it with aqueous uranium bicarbonate solution, perform conventional post-treatment, purify by chromatography, elute with n-hexane, and recrystallize from ethanol to obtain 38.9 g of a white solid (compound BYLC-02), LC : 99.6%, yield: 82.5%.

[0081] The obtained white solid BYLC-02 was analyzed by GC-MS, and the m / z of the product was 472.1 (M+).

[0082] 1 H-NMR (300MHz, CDCl 3 ...

Embodiment 3

[0084]

[0085] The synthetic route for preparing compound BYLC-03 is as follows:

[0086]

[0087] Specific steps are as follows:

[0088] (1) Synthesis of compound BYLC-03-1:

[0089]Under the protection of nitrogen, add 40.5g 3-benzyloxy-7-bromo-4,6-difluorodibenzothiophene and 300ml tetrahydrofuran into the reaction flask, cool down to -70℃~-80℃, add dropwise 0.13mol n-butyl Lithium base, temperature control -70℃~-80℃, react for 1h, add 18.0g trimethyl borate dropwise, return to -30℃ naturally, acidify with dilute hydrochloric acid to adjust the pH value to less than 2, carry out conventional post-treatment, and recrystallize to obtain shallow Yellow solid (compound BYLC-03-1) 32.3g, LC: 98.5%, yield 87.3%;

[0090] (2) Synthesis of compound BYLC-03-2:

[0091] Add 32.3g of compound BYLC-03-1, 18.5g of p-bromoiodobenzene, 18.0g of anhydrous potassium carbonate, 200ml of toluene, 150ml of ethanol, 150ml of water, 0.3g of tetrakistriphenylphosphine palladium into th...

technical field

[0001] The invention belongs to the field of liquid crystal compounds and applications thereof, and relates to a dibenzothiophene polymerizable compound and applications thereof. Background technique

[0002] In recent years, liquid crystal display devices have developed more and more rapidly. The application of liquid crystal materials as environmental materials in information display materials, organic optoelectronic materials and other fields has great research value and bright application prospects, and different types have also been developed, such as vehicle-mounted small Liquid crystal display devices, portable liquid crystal display devices, ultra-thin liquid crystal display devices, etc., are making progress in the development of this field. Taking TV as an example, it is characterized by light weight, small space occupation, and easy movement. There are also notebook-type personal computers, Pocket PCs, mobile phones, etc., commercial TFT-LCD produc...

Examples

Embodiment 1

[0058] The structural formula of the liquid crystal compound is:

[0059]

[0060] The synthetic route for preparing compound BYLC-01 is as follows:

[0061]

[0062] Specific steps are as follows:

[0063] (1) Synthesis of compound BYLC-01-1:

[0064] Add 40.5g of 3-benzyloxy-7-bromo-4,6-difluorodibenzothiophene, 20g of diethyl malonate, 14g of potassium tert-butoxide, and 300ml of tetrahydrofuran into the reaction flask, and control the temperature at 50°C to 60°C React at ℃ for 6 hours, lower to room temperature, adjust the pH value to neutral with dilute hydrochloric acid, perform conventional post-treatment, and recrystallize to obtain 43.5 g of light yellow solid (compound BYLC-01-1), HPLC: 99.4%, yield 85.0%;

[0065] (2) Synthesis of compound BYLC-01-2:

[0066] Add 10.0g of aluminum hydride and 500mL of tetrahydrofuran into the reaction flask, cool down to 0°C, control the temperature at 0°C to 10°C, add dropwise a solution composed of 43.5g of compound BYLC-...

Embodiment 2

[0074] The structural formula of the liquid crystal compound is:

[0075]

[0076] The synthetic route for preparing compound BYLC-02 is as follows:

[0077]

[0078] Specific steps are as follows:

[0079] Synthesis of compound BYLC-02:

[0080] Under the protection of nitrogen, add 31.0g of compound BYLC-01-3, 38.4g of triethylamine and 250mL of dichloromethane into the reaction flask, cool down to -10°C, control the temperature from -10°C to 0°C, and add 32.0g of acryloyl chloride dropwise, Rise to room temperature and react for 6 hours. Pour the reaction solution into water, neutralize it with aqueous uranium bicarbonate solution, perform conventional post-treatment, purify by chromatography, elute with n-hexane, and recrystallize from ethanol to obtain 38.9 g of a white solid (compound BYLC-02), LC : 99.6%, yield: 82.5%.

[0081] The obtained white solid BYLC-02 was analyzed by GC-MS, and the m / z of the product was 472.1 (M+).

[0082] 1 H-NMR (300MHz, CDCl 3 ...

Embodiment 3

[0084]

[0085] The synthetic route for preparing compound BYLC-03 is as follows:

[0086]

[0087] Specific steps are as follows:

[0088] (1) Synthesis of compound BYLC-03-1:

[0089]Under the protection of nitrogen, add 40.5g 3-benzyloxy-7-bromo-4,6-difluorodibenzothiophene and 300ml tetrahydrofuran into the reaction flask, cool down to -70℃~-80℃, add dropwise 0.13mol n-butyl Lithium base, temperature control -70℃~-80℃, react for 1h, add 18.0g trimethyl borate dropwise, return to -30℃ naturally, acidify with dilute hydrochloric acid to adjust the pH value to less than 2, carry out conventional post-treatment, and recrystallize to obtain shallow Yellow solid (compound BYLC-03-1) 32.3g, LC: 98.5%, yield 87.3%;

[0090] (2) Synthesis of compound BYLC-03-2:

[0091] Add 32.3g of compound BYLC-03-1, 18.5g of p-bromoiodobenzene, 18.0g of anhydrous potassium carbonate, 200ml of toluene, 150ml of ethanol, 150ml of water, 0.3g of tetrakistriphenylphosphine palladium into th...

Images