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Alkenyl side-chain conjugated indacenodifuranyl polymer material as well as preparation method and application thereof

A polymer material, furan-based technology, used in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve the problem of reducing the degree of conjugation of IDT units, the contribution of π-conjugated systems of IDT units, and the light absorption capacity of polymers. The effect is not ideal and other problems, to achieve the effect of good photovoltaic performance, good photophysical performance and electrochemical performance

Inactive Publication Date: 2020-04-17
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported modification methods are still unsatisfactory in terms of broadening the polymer absorption spectrum and increasing the light absorption capacity of the polymer, so exploring new modification strategies is also the goal of researchers.
[0004] In general, IDT unit 4, 9-bit SP 3 The side chain connected by the hybrid carbon atom does not contribute to the formation of the π-conjugated system of the IDT unit, but the degree of conjugation of the IDT unit is reduced due to the steric hindrance of the side chain

Method used

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  • Alkenyl side-chain conjugated indacenodifuranyl polymer material as well as preparation method and application thereof
  • Alkenyl side-chain conjugated indacenodifuranyl polymer material as well as preparation method and application thereof
  • Alkenyl side-chain conjugated indacenodifuranyl polymer material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Synthesis of difuran-based polymer material (PIDF-TC6C8-BT) with conjugated alkenyl side chain

[0055] The synthetic route is as follows:

[0056]

[0057] (1) Synthesis of compound 2

[0058] With 2,5-dibromo-diethyl terephthalate (1.52g, 4.0 mmol), 2-tributyltinfuran (2.90g, 9.2mmol), three (dibenzylideneacetone) two palladium (0.037g, 0.04 mmol), tris(o-methylphenyl)phosphine (0.013 g, 0.044 mmol) were placed in a 100 mL single-necked flask, vacuumed and filled with nitrogen cyclically 2-3 times, and 50 mL of anhydrous toluene was added under the protection of nitrogen . Place the reaction flask in an oil bath and heat to 120 o C overnight (14~16h). After the mixture was cooled to room temperature, the mixed liquid was poured into deionized water, and the aqueous phase was extracted with 3×30 mL of dichloromethane. The organic phases were combined, washed with a saturated aqueous sodium chloride solution, the organic phases were collected and dried over anhydrous magne...

Embodiment 2

[0075] The specific process is the same as in Example 1, except that 1-bromo-2-hexyl-decane in step (5) is replaced by n-hexadecane.

[0076] Add IDF-T-C16 (0.20 mmol, 206.5 mg), 4,7-dibromo-2,1,3-bisfluorobenzothiadiazole (0.21 mmol, 60.3 mg), tetrakis (triphenylphosphine) palladium (11.56mg, 0.01mmol) is added to the N 2 Protect the device in a 25.0 mL single-necked flask. Then, evacuate and fill with nitrogen cyclically 3-4 times, and inject 10 mL of anhydrous toluene and 1 mL of anhydrous N,N-dimethylformamide with a syringe under the protection of nitrogen. After the addition, the mixture was evacuated again and filled with nitrogen. Then quickly heat to 120 o C reflux the reaction, and observe the change in the viscosity of the mixture. When the rotor speed in the reaction flask slows down and the mixture becomes viscous, use a syringe to inject 0.1 mL of 2-tributylstannane furan, and continue to stir for 2.0 h. Then use a syringe to inject 0.1 mL of p-bromofluorobenzene...

Embodiment 3

[0080] The alkenyl side chain conjugated difuran-based polymer materials (PIDF-TC6C8-BT and PIDF-TC16-BT) prepared in Example 1-2 were dissolved in chloroform to form 10 -4 mg / mL solution, and use a pipette to measure 60μL of chloroform solution spin-coated on pretreated quartz glass (15mm×15mm), air dry, test the UV-visible absorption spectrum of the polymer film, see details Figure 4 . According to formula E gap =1240 / λ onset It is calculated that the optical energy gaps of PIDF-TC6C8-BT and PIDF-TC16-BT under the spectrum are both 1.57eV, which are narrow band gap polymer materials.

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Abstract

The invention discloses an alkenyl side chain conjugated indacenodifuranyl polymer material as well as a preparation method and an application thereof. The structural formula of the alkenyl side-chainconjugated indacenodifuranyl polymer material is shown in the specification, wherein R is n-hexyl, n-octyl, n-hexadecyl, n-hexadecyl, or other alkanes and aromatic hydrocarbons, and n is 9-20; furthermore, the series of polymers PIDF-TCx-BT designed and synthesized by the invention have a relatively high conjugate plane, a relatively high HOMO energy level, relatively wide light capturing capability and a relatively good electron energy level; wherein polymers PIDF-TC6C8-BT and PIDF-TC16-BT of which the side chains are 2-hexyldecyl and hexadecyl are taken as examples, the tests find that thephotoelectric conversion efficiency of a battery prepared from the alkenyl side chain conjugated indacenodifuranyl polymer material prepared by the invention can be greater than 7% under optimizationtreatment, and the product has great photovoltaic potential.

Description

Technical field [0001] The invention covers the fields of organic synthetic chemistry and functional material chemistry, and in particular relates to a difuran-based polymer material with conjugated alkenyl side chains, and a preparation method and application thereof. Background technique [0002] With the rapid development of the world, the reserves of traditional fossil energy are gradually decreasing. At the same time, the social and environmental problems caused by the massive consumption of fossil energy are increasing. Therefore, the search for new energy is considered to be related to the country’s economic and social development, the improvement of people’s lives, and the society. The important issue of long-term stability is also the top priority to fully guarantee the world's energy security. Solar energy is considered to be the most promising new energy source for development in the 21st century and beyond due to its clean, environmentally friendly, abundant reserves,...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/42H01L51/46
CPCC08G61/125C08G61/123C08G2261/124C08G2261/1414C08G2261/146C08G2261/18C08G2261/3242C08G2261/3246C08G2261/414C08G2261/91H10K85/111H10K85/151H10K30/00Y02E10/549
Inventor 高跃岳谭付瑞刘荣董琛张伟风
Owner HENAN UNIVERSITY
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