Naphthalene series liquid crystal monomer compound containing isothiocyano group as well as preparation method and application of naphthalene series liquid crystal monomer compound

A liquid crystal monomer and isothiocyanate technology, applied in chemical instruments and methods, liquid crystal materials, organic chemistry, etc., to achieve high birefringence, simple preparation method, and improve the effect of clearing point

Pending Publication Date: 2022-03-22
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no liquid crystal material that can fully meet the above conditions at the same time.

Method used

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  • Naphthalene series liquid crystal monomer compound containing isothiocyano group as well as preparation method and application of naphthalene series liquid crystal monomer compound
  • Naphthalene series liquid crystal monomer compound containing isothiocyano group as well as preparation method and application of naphthalene series liquid crystal monomer compound
  • Naphthalene series liquid crystal monomer compound containing isothiocyano group as well as preparation method and application of naphthalene series liquid crystal monomer compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] in formula middle

[0084] with R 1 The structure is -C 2 h 5 , R 2 The structure is -n-C 5 h 11 For example, Y 1 , Y 2 =H (abbreviated as 5BTNENCS), introduces the synthesis method of the isothiocyanate-containing naphthalene series liquid crystal monomer compound:

[0085] Step 1: Synthesis of intermediate m1:

[0086] Add 118.50g (0.5mol) of 2-bromo-6-methoxynaphthalene and 826g of dichloroethane into a 2L three-necked flask, cool down to -10-0°C, and add 79.98g (0.6mol) of aluminum trichloride. Add 47.10 g (0.6 mol) of acetyl chloride dropwise. After the addition is complete, the temperature of the system is raised to 0-10°C. Insulation reaction 2h. Hydrolyzed, the organic phase was washed to neutrality. The solvent was removed to obtain 122.0 g of light yellow solid m1, the GC purity was ≥94%, and the yield was 87.41%.

[0087] Step 2: Synthesis of intermediate m2

[0088] Add 122.00g (0.44mol) of intermediate m1 and 610.00g of diethylene glycol into...

Embodiment 2

[0101] in formula middle

[0102] with R 1 The structure is -C 2 h 5 , R 2 The structure is -n-C 5 h 11 As an example (abbreviated as 5PTNENCS), the synthesis method of this isothiocyano-containing naphthalene series liquid crystal monomer compound is introduced:

[0103] Step 1: Synthesis of intermediate m1

[0104] Put 7.6g (43mmol) of 4-pentyl-1-phenylacetylene, 10g (39mmol) of the compound (intermediate m3 in Example 1), and 60.0g of triethylamine into a 250mL three-necked flask. Stir the system to dissolve, and use nitrogen to fully replace the air in the system. Catalyst 0.2804g (0.4mmol) PdCl 2 (PPh 3 ) 2 , 0.1524g (0.8mmol) CuI, 0.3144g (1.2mmol) PPh 3 , 0.4848g (4mmol) of DMAP was put into the system, the temperature was raised to an internal temperature of 85-90°C, and the reaction was kept for 8 hours. Triethylamine was distilled off under atmospheric pressure, 200 g of toluene was added, suction filtered, the filtrate was washed with water until neutr...

Embodiment 3

[0110] in formula middle

[0111] with R 1 The structure is -C 2 h 5 , R 2 The structure is -n-C 3 h 7 As an example (abbreviated as 3HPTNENCS), the synthesis method of this isothiocyano-containing naphthalene series liquid crystal monomer compound is introduced:

[0112] Step 1: Synthesis of intermediate m1

[0113] Put 8.8g (0.045mol) 1-ethynyl-4-(4-propylcyclohexyl)benzene, 7.5g (0.03mol) compound (intermediate m3 in Example 1), 60.0g triethylamine into 250mL three ports in the bottle. Stir the system to dissolve, and use nitrogen to fully replace the air in the system. Catalyst 0.2103g (0.3mmol) PdCl 2 (PPh 3 ) 2 , 0.1143g (0.6mmol) CuI, 0.2358g (0.9mmol) PPh 3 , 0.3836g (3mmol) of DMAP was put into the system, the temperature was raised to 85-90°C, and the reaction was kept for 8h. Triethylamine was distilled off under atmospheric pressure, 200 g of toluene was added, suction filtered, the filtrate was washed with water until neutral, and the organic phase ...

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Abstract

The invention relates to an isothiocyano group-containing naphthalene series liquid crystal monomer compound, and belongs to the technical field of liquid crystal materials, the structural formula of the liquid crystal monomer compound is shown as follows: R1 and R2 are independently selected from any one of alkyl and alkoxy; x is any one of a phenyl group, a biphenyl group, a benzyne group and a biphenyl alkynyl group. The naphthalene series liquid crystal monomer compound containing the isothiocyano group is applied to a liquid crystal composition, a liquid crystal display and a high-frequency technical component, and the high-frequency technical component is a liquid crystal-based antenna element, a phase shifter, a tunable optical filter or a tunable metamaterial structure. The naphthalene-series liquid crystal compound containing the isothiocyano group has a relatively high birefringence, a relatively wide nematic phase temperature, relatively high anisotropy and dielectric constant and capability of improving the performance of a liquid crystal component, and the clearing point of the liquid crystal component can be improved.

Description

technical field [0001] The invention relates to a naphthalene series liquid crystal monomer compound containing isothiocyanate, a preparation method and an application thereof, and belongs to the technical field of liquid crystal materials. Background technique [0002] One of the main characteristics of liquid crystals is birefringence with refractive index anisotropy. With the continuous development of liquid crystal display technology and the continuous improvement of people's requirements for liquid crystal display. Liquid crystal materials with fast response, low viscosity and high birefringence have become a focus of attention. It is well known that liquid crystal monomers with high birefringence tend to have high viscosity. High birefringence and low viscosity are mutually contradictory. However, liquid crystal monomers with relatively high birefringence and relatively low viscosity can be obtained through molecular design. group. The isothiocyanate-containing na...

Claims

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Application Information

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IPC IPC(8): C07C331/28C09K19/32G02F1/1333
CPCC07C331/28C09K19/322G02F1/1333
Inventor 王连义孙德生胡葆华牟霖蕾周上群宣力琪
Owner VALIANT CO LTD
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