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Narrow-band gap polymer based on benzobithiadiazole or thiadiazole quinoxaline as well as preparation method and application of narrow-band gap polymer

A technology of thiadiazole quinoxaline and benzobisthiadiazole is applied in the field of narrow-bandgap polymers and their preparation, which can solve the problems of high toxicity of organic tin salts, complicated synthesis steps and the like, and achieves few synthesis steps and high electron density. Mobility, simple preparation effect

Pending Publication Date: 2022-03-11
THE CHINESE UNIV OF HONG KONG SHENZHEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In addition, in the past, the synthesis of such polymers was mostly obtained through traditional coupling methods (such as Suzuki coupling reaction and Stille coupling reaction), which have the disadvantages of cumbersome synthesis steps and high toxicity of organotin salts.

Method used

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  • Narrow-band gap polymer based on benzobithiadiazole or thiadiazole quinoxaline as well as preparation method and application of narrow-band gap polymer
  • Narrow-band gap polymer based on benzobithiadiazole or thiadiazole quinoxaline as well as preparation method and application of narrow-band gap polymer
  • Narrow-band gap polymer based on benzobithiadiazole or thiadiazole quinoxaline as well as preparation method and application of narrow-band gap polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] This embodiment provides a narrow bandgap polymer, its structural formula is:

[0061]

[0062] Among them, R 2 For 2-octyl dodecyl.

[0063] The preparation method and reaction equation of this polymer are as follows:

[0064]

[0065] Trisdibenzylideneacetone dipalladium (Pd 2 (dba) 3 ) is the catalyst, and three p-benzyloxyphosphorus ((o-MeOPh) 3 P) is the ligand of the above catalyst, potassium carbonate (K 2 CO 3 ) plays the role of neutralizing the acid produced by the reaction and activating the catalyst, trimethylacetic acid (PivOH) acts as a catalytic proton shuttle, cooperates with the palladium center to reduce the cracking energy of the C-H bond, and promotes the reaction. 0.097mmol compound 2, 0.097mmol compound 5, 0.005mmol tridibenzylidene acetone dipalladium (Pd 2 (dba) 3 ), 0.01mmol tri-p-phenylmethoxyphosphorus ((o-MeOPh) 3 P), 0.05mmol trimethylacetic acid (PivOH) and 0.5mmol potassium carbonate (K 2 CO 3 ) was dissolved in 0.5 mL o-x...

Embodiment 2

[0068] This embodiment provides a narrow bandgap polymer, its structural formula is:

[0069]

[0070] Among them, R 2 For 2-octyl dodecyl.

[0071] The preparation method and reaction equation of this polymer are as follows:

[0072]

[0073] The mechanism, process and aftertreatment of this reaction are the same as in Example 1. The dosage is: 0.092mmol compound 2, 0.092mmol compound 6, 0.005mmol tridibenzylidene acetone dipalladium (Pd 2 (dba) 3 ), 0.01mmol tri-p-phenylmethoxyphosphorus ((o-MeOPh) 3 P), 0.05mmol trimethylacetic acid (PivOH) and 0.5mmol potassium carbonate (K 2 CO 3 ) was dissolved in 0.46mL o-xylene. The final post-treatment gave the above-mentioned polymer, denoted as polymer 11, with a yield of 92%.

[0074] figure 2 For the proton nuclear magnetic spectrum (500MHz, C of the polymer 11 that embodiment 2 obtains 2 D. 2 Cl 4 , 100°C).

Embodiment 3

[0076] This embodiment provides a narrow bandgap polymer, its structural formula is:

[0077]

[0078] Among them, R 2 is 2-octyldodecyl, R 6 For dodecyl.

[0079] The preparation method and reaction equation of this polymer are as follows:

[0080]

[0081] The mechanism, process and aftertreatment of this reaction are the same as in Example 1. The dosage is: 0.092mmol compound 2, 0.092mmol compound 7, 0.005mmol tridibenzylidene acetone dipalladium (Pd 2 (dba) 3 ), 0.01mmol tri-p-phenylmethoxyphosphorus ((o-MeOPh) 3 P), 0.05mmol trimethylacetic acid (PivOH) and 0.5mmol potassium carbonate (K 2 CO 3 ) was dissolved in 0.46mL o-xylene. The final post-treatment gave the above-mentioned polymer, denoted as polymer 12, with a yield of 38%.

[0082] image 3 For the proton nuclear magnetic spectrum (500MHz, C of the polymer 12 that embodiment 3 obtains 2 D. 2 Cl 4 , 100°C). Polymer 12 can confirm that the two monomers have been copolymerized through NMR spectra ...

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Abstract

The invention provides a narrow-band gap polymer based on benzobis (thiadiazole) or thiadiazole quinoxaline as well as a preparation method and application of the narrow-band gap polymer. The invention discloses a narrow-band gap polymer based on benzobithiadiazole or thiadiazole quinoxaline. The narrow-band gap polymer is obtained by polycondensation of an electron acceptor and an electron donor or polycondensation of different electron acceptors. The preparation method comprises the following steps: mixing raw materials including an electron acceptor and an electron donor or different electron acceptors and ligands, a catalyst and an organic solvent, and heating to react to obtain a product. The narrow-band-gap polymer can be used for organic light-emitting diodes, polymer solar cells, organic photovoltaics, organic light detectors and photo-thermal conversion devices. According to the narrow-band gap polymer provided by the invention, the special optical and potential electrochemical properties can help to develop better n-type and bipolar polymer semiconductors and conductors.

Description

technical field [0001] The application relates to the field of new materials, in particular to a narrow bandgap polymer based on benzobisthiadiazole or thiadiazoquinoxaline and its preparation method and application. Background technique [0002] Organic π-conjugated small molecules and polymers are promising semiconductor materials for a new generation of optoelectronic devices due to their light weight, solution processability, mechanical flexibility, and various finely tunable structures and properties synthesized. The optoelectronic properties and device performance of DA copolymers can be tuned conveniently by selecting π-conjugated building blocks with different chemical structures. For example, the use of strong acceptor units leads to n-type mobility of low bandgap polymers above 1 cm 2 / Vs. Some strong acceptor units have been reported, such as diketopyrrole (DPP), naphthalene diimide (NDI) and isoindigo (IID). [0003] Finding more π-conjugated building blocks w...

Claims

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Application Information

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IPC IPC(8): C08G61/12
CPCC08G61/126C08G61/123C08G61/122C08G61/124C08G2261/124C08G2261/3223C08G2261/3246C08G2261/3241C08G2261/3243C08G2261/3242C08G2261/514C08G2261/94C08G2261/91C08G2261/95C08G2261/52Y02E10/549
Inventor 王明锋江烽邓显君
Owner THE CHINESE UNIV OF HONG KONG SHENZHEN
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