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Fused-ring polymer donor material based on benzothiadiazole or benzoselenadiazole and preparation method of fused-ring polymer

A technology of benzothiadiazole and benzoselenodiazole, which is applied in the field of conjugated polymers of benzothiadiazole units and its preparation, to achieve strong light absorption range, low HOMO energy level, and high atom economy Effect

Active Publication Date: 2021-12-07
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 benzoselenadiazole and preparation method of fused-ring polymer
  • Fused-ring polymer donor material based on benzothiadiazole or benzoselenadiazole and preparation method of fused-ring polymer
  • Fused-ring polymer donor material based on benzothiadiazole or benzoselenadiazole and preparation method of fused-ring polymer

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Experimental program
Comparison scheme
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

[0076] The molecular weight of embodiment 2, polymer P1 and P2

[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.

Embodiment 3

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

[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.

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Abstract

The invention relates to a fused-ring polymer donor material based on benzothiadiazole or benzoselenadiazole and a preparation method of the fused-ring polymer donor material. Two conjugated polymers involved in the invention have wide and strong absorption in a visible-near infrared region. Meanwhile, an alkyl side chain is introduced to an N site of a five-membered heterocycle connected between benzodiazole and thiophene, so that good solubility is provided, solution processing is facilitated, and the polymer serving as a semiconductor active layer donor material has potential application prospects in organic solar cell devices. The two conjugated polymers are formed through hydrocarbon activation polymerization. The method is simple in synthesis step and free of metal by-products, and the polymer with higher molecular weight and fewer structural defects can be obtained. The polymerization method disclosed by the invention aims to accord with the principle 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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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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