Synthesis and application of novel functional material based on diazosulfide

A technology of benzothiadiazole and functional materials, applied in the direction of luminescent materials, liquid crystal materials, color-changing fluorescent materials, etc., can solve the problems of unreported complex liquid crystal phase and phase structure, and achieve high-efficiency luminous performance and liquid crystal performance, the effect of improving liquid crystal performance and solubility performance

Active Publication Date: 2019-06-14
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research on liquid crystal compounds based on 2,1,3-benzothiadiazole is still in an initial stage, and many complex liquid crystal phases have not been reported exactly.
Although liquid crystal behavior similar to columnar phase liquid crystal texture has been found in some molecules with multiple alkyl chains at the end, that is, multi-chain molecules, the exact phase structure has not been reported yet.

Method used

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  • Synthesis and application of novel functional material based on diazosulfide
  • Synthesis and application of novel functional material based on diazosulfide
  • Synthesis and application of novel functional material based on diazosulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] Under ice-cooling, add 4,7-dibromo-2,1,3-benzothiadiazole (6.0 g, 20.5 mmol) and H 2 SO 4 (12 mL), followed by slow dropwise addition of HNO 3 (24 mL). After reacting at room temperature for 6 hours, the reactant was poured into ice water, and suction filtered to obtain 5.12 g of a yellow solid (yield 73%). 1 H NMR (400 MHz, CDCl 3 ) δ 8.28 (s, 1H).

Embodiment 2

[0023]

[0024] Add 4,7-dibromo-2,1,3-benzothiadiazole-5-nitro (5.0 g, 14.7 mmol) and glacial acetic acid (120 mL) into a 200 mL two-necked flask, place in an ice bath, and separate Iron powder (4.2 g, 73.7 mmol) was added in batches. After reacting at room temperature for 12 hours, the reactant was poured into ice water, and suction filtered to obtain 4.3 g of a tan solid (95% yield). 1 H NMR (400 MHz, CDCl 3 ) δ 7.47 (s,1H), 4.64 (s, 2H).

Embodiment 3

[0026]

[0027]

[0028]

[0029]

[0030] Preparation of compound sm1

[0031] Add 4,7-dibromo-2,1,3-benzothiadiazol-5-amine (1.0 g, 3.24mmol), 4-tert-butylphenylboronic acid (1.0 g, 7.14mmol ), tetrakistriphenylphosphine palladium (187mg, 0.0162mmol), ethanol (10 mL), toluene (30 mL) and 2M potassium carbonate aqueous solution (10 mL), the mixture was refluxed under nitrogen for 24 hours. After the reactants were cooled to room temperature, the mixture was washed with CH 2 Cl 2 (3×30 mL) extraction; the organic layer was successively washed with water (60 mL), dried, and evaporated under reduced pressure to remove the solvent; the residue was column layered with petroleum ether:dichloromethane (V:V=1:2) as the eluent After separation and recrystallization, 430 mg of the target product was obtained (yield: 39%). 1 H NMR (300 MHz, CDCl 3 ) δ 7.86 (d, J = 8.4 Hz, 2H), 7.61-7.53 (m, 6H),7.28 (s, 1H), 4.25 (s, 2H), 1.40 (s, 19H).

[0032] Preparation of compoun...

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PUM

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Abstract

The invention discloses a novel functional material based on diazosulfide and application thereof. The material is a liquid crystal luminescent material prepared by taking a diazosulfide rigid unit asa luminescent core and introducing an alkyl chain or a liquid crystal element into the lateral part of a molecular rigid skeleton. Through the structure, luminescence property can be adjusted by adjusting the energy gaps of group regulatory molecules at two ends of the luminescent core unit; the liquid crystal element on the side wall of the molecular structure is capable of effectively regulating and controlling the liquid crystal property, so that a high-efficiency liquid crystal luminescent material can be acquired; the material has abundant photophysical performance; the luminescent color of the material changes along with the change of external conditions; when the material is used as a luminescent layer dopant for preparing an organic light-emitting device, the maximal external quantum efficiency of device is 1.20%.

Description

technical field [0001] The present invention relates to a new type of multifunctional material, in particular to the synthesis and application of a new type of functional material based on benzothiadiazole: using benzothiadiazole derivatives and benzoic acid derivatives to obtain liquid crystal, The invention relates to a multifunctional material with properties such as chromism and acid chromism; it also relates to the application of this kind of material as a light-emitting doped layer to prepare an electroluminescent diode, and belongs to the technical field of organic photoelectric materials. Background technique [0002] 2,1,3-Benzothiadiazole has the advantages of strong electron affinity, coplanarity and good adjustment of the energy gap of the compound, and is widely used in the construction of conjugated compounds in the field of semiconductors. Such as organic electroluminescent diodes, organic solar cells, and light-harvesting materials. Because of the good plana...

Claims

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Application Information

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IPC IPC(8): C07D417/14C07D285/14C09K9/02C09K11/06C09K19/34H01L51/54
Inventor 王亚飞钱高威朱卫国
Owner CHANGZHOU UNIV
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