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Fused ring polymer donor material based on benzothiadiazole or benzoselenodiazole and preparation method thereof

A technology of benzothiadiazole and benzoselenadiazole, which achieves the effects of high atomic economy, improved planarity and strong light absorption range

Active Publication Date: 2022-06-14
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most DArP defects (e.g., β-defects, branching, cross-linking, homo-coupling) will still be embedded in the polymer structure compared to by-products in C–H functionalization reactions of small molecules, which are usually easy to isolate, which is The main bottleneck of its mass production

Method used

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  • Fused ring polymer donor material based on benzothiadiazole or benzoselenodiazole and preparation method thereof
  • Fused ring polymer donor material based on benzothiadiazole or benzoselenodiazole and preparation method thereof
  • Fused ring polymer donor material based on benzothiadiazole or benzoselenodiazole and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0051] Example 1. Preparation of conjugated polymers based on benzothiadiazole and benzoselenodiazole units

[0052] This example provides two soluble conjugated polymers based on benzothiadiazole or benzoselenodiazole units, the structural formulas of which are shown in Table 1, and their synthetic routes can be found in figure 1 .

[0053] Table 1

[0054]

[0055] 1.1. Preparation of monomer M1

[0056] The synthetic route of the first monomer M1 of the two polymers is exactly the same, which specifically includes the following steps:

[0057] Synthesis of a, 7-bromo-5-nitro-4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole:

[0058] Under argon conditions, 4,7-dibromo-5-nitrobenzo[c][1,2,5]thiadiazole (i.e. starting material A, synthetic reference patent literature: CN109879870A based on benzothiadiazole Synthesis and application of new functional materials of oxadiazole) (3.3896g, 10mmol), 2-(tributyltin-based) thiophene (3.7319g, 10mmol) and 50mL of dry THF were added t...

Embodiment 2

[0077] Adopt gel permeation chromatography to test the molecular weight of two kinds of donor materials: the number average molecular weight (M) of P1 and P2 n ) are 103.8kDa, 56.2kDa respectively, weight average molecular weight (M w ) were 359.8kDa and 310.0kDa, respectively, and the polydispersity index PDI were 3.46 and 5.51, respectively.

[0078] The thermogravimetric curve of embodiment 3, polymer P1 and P2

Embodiment 3

[0079] From the TGA curves, it can be seen that under an inert atmosphere, the decomposition temperatures corresponding to 5% mass loss of polymers P1 and P2 reach 435°C and 350°C respectively, indicating that they have good thermal stability, showing that the two can be used as donor materials Applications in organic solar cell devices and other optoelectronic device requirements.

[0080] The ultraviolet-visible absorption spectrum of embodiment 4, polymer P1 and P2

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Abstract

The invention relates to a fused-ring polymer donor material based on benzothiadiazole or benzoselenodiazole and a preparation method thereof. The two conjugated polymers involved in the present invention have broad and strong absorption in the visible-near infrared region. At the same time, the introduction of alkyl side chains on the N site of the five-membered heterocyclic ring connected between benzodiazole and thiophene provides good solubility for the present invention, so it helps solution processing, so the present invention is used as a semiconductor active layer donor The material has potential applications in organic solar cell devices. The two conjugated polymers in the present invention are formed by activated polymerization of hydrocarbons. The method has simple synthesis steps, has no metal by-products, and can obtain polymers with higher molecular weight and fewer structural defects. The polymerization method involved in the present invention is intended to comply with the principles of green chemistry.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and in particular relates to a conjugated polymer based on heteroatom-substituted benzothiadiazole units and a preparation method thereof. Background technique [0002] Organic solar cells have attracted much attention due to their advantages such as low preparation cost, easy adjustment of function and structure, good flexibility and film-forming properties, and easy fabrication of large-area flexible devices. [0003] In terms of material structure, the heavy atom substitution effect in conjugated polymers has gradually become a research hotspot. Through the introduction of "heavy" atoms (below S in group VIA) and a relatively simple synthetic route, a narrow highest occupied molecular orbital (HOMO)-lowest Donor material that does not occupy a molecular orbital (LUMO) gap (<1eV). Among the broad range of donor repeating units, a few structures are widely used in heavy atom ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12
CPCC08G61/124C08G61/126C08G61/123C08G2261/11C08G2261/1412C08G2261/3241C08G2261/3243C08G2261/3246C08G2261/3247C08G2261/91
Inventor 邓平钱皓晨孟岩
Owner FUZHOU UNIV
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