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Preparation method and application of a wide bandgap star non-fullerene small molecule acceptor

A small molecule acceptor, non-fullerene technology, applied in semiconductor/solid-state device manufacturing, electric solid-state devices, semiconductor devices, etc., can solve the problems of large phase separation, poor morphology, affecting the energy conversion efficiency of organic solar cells, etc. , to achieve the effect of high energy conversion efficiency

Active Publication Date: 2020-03-03
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Small molecule acceptors usually have good crystallinity, and after blending with polymer donor materials to form an active layer, they will form a large phase separation, resulting in poor morphology, which affects the energy conversion efficiency of organic solar cells, Therefore, the development of small molecule receptors with three-dimensional structure can effectively solve this problem

Method used

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  • Preparation method and application of a wide bandgap star non-fullerene small molecule acceptor
  • Preparation method and application of a wide bandgap star non-fullerene small molecule acceptor
  • Preparation method and application of a wide bandgap star non-fullerene small molecule acceptor

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Embodiment 1

[0024] An organic small molecule receptor with a chemical structure of 2,7,12-TrBRCN, the synthesis route of which is as follows:

[0025]

[0026] Compound 1 can be reported according to literature (J.Am.Chem.Soc., 2016, 138, 2528-2531; J.Am.Chem.Soc., 2015, 137, 3901-3909; Nature Communications, 2016, 7, 12469) step synthesis. Compound 5 can be synthesized according to the steps reported in the literature (J.Am.Chem.Soc., 2015, 137, 898-904).

[0027] Synthesis of compound 2: Dissolve compound 1 (0.30g, 0.39mmol), diboronic acid pinacolone ester (0.69g, 2.70mmol) potassium acetate (0.30g, 3.05mmol) in dry DMF (30mL), remove oxygen , under nitrogen protection, adding PdCl 2 (dppf) 2 (0.029g, 0.04mmol), reflux for 48h. After the reaction, DMF was removed under reduced pressure, extracted with dichloromethane, and dried over anhydrous magnesium sulfate. After filtration, the crude product was separated and purified by column chromatography (silica gel; eluent: petroleum...

Embodiment 2

[0035] A small organic molecule receptor with a chemical structure of 3,8,13-TrBRCN, the synthesis route of which is as follows:

[0036]

[0037] Compound 4 can be synthesized according to the steps reported in literature (Chem. Eur. J. 2015, 21, 13052-13057).

[0038] Synthesis of Compound 5: Compound 4 (3.28g, 15.6mmol), p-toluenesulfonic acid monohydrate (12.7g, 66.6mmol), propionic acid (3.69g, 49.7mmol) were dissolved in 15mL o-dichlorobenzene. The reaction solution was heated to 105°C and stirred for 16h. After cooling to room temperature, the reaction solution was poured into methanol, neutralized with sodium hydroxide, and the solid was collected by filtration. The obtained solid was washed with methanol and ethanol, and recrystallized with tetrachloroethane to obtain product 5 as a pale yellow solid (2.54 g, yield: 84%).

[0039] Synthesis of compound 6: Compound 5 (1.1 g, 1.91 mmol) and potassium tert-butoxide (4.28 g, 38.2 mmol) were added to dry tetrahydrofur...

Embodiment 3

[0049] Absorption Spectra Measurement of Small Organic Molecule Receptors 2,7,12-TrBRCN and 3,8,13-TrBRCN

[0050] figure 1 and figure 2 UV-Vis absorption spectra of small molecule acceptors 2,7,12-TrBRCN and 3,8,13-TrBRCN in chloroform solution and on quartz plate, respectively.

[0051] Depend on figure 1It can be seen that the maximum absorption value of 2,7,12-TrBRCN film is about 475nm, the peak value is about 575nm, and its optical bandgap is 2.16eV (the optical bandgap is based on the formula E g =1240 / λ onset calculation, where E g is the optical bandgap, λ onset is the peak value of film absorption).

[0052] Depend on figure 2 It can be seen that the maximum absorption value of 3,8,13-TrBRCN film is about 500nm, the peak value is about 600nm, and its optical bandgap is 2.07eV (the optical bandgap can be calculated according to the formula E g =1240 / λ onset calculation, where E g is the optical bandgap, λ onset is the maximum absorption sideband value abs...

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Abstract

The invention discloses a preparation method for a broad-band gap star-shaped non-fullerene micromolecule receptor and application of the receptor in an organic solar battery. The structural formula of micromolecules is of formula I as shown in the specification. The micromolecule receptor material with broad-band gaps, which is disclosed by the invention, has relatively good electron conduction properties and is in good absorption complementation and energy matching with a narrow-band gap polymer donor material PTB7-Th and the like. The micromolecule receptor is applied to the organic solar battery, open circuit voltage of 0.95V and energy conversion efficiency of about 8.23-10.14% can be acquired, and the application prospect of the broad-band gap star-shaped non-fullerene micromoleculereceptor in the organic photovoltaic field is sufficiently widened.

Description

technical field [0001] The invention belongs to the field of organic semiconductor materials, and relates to a star-shaped small molecule acceptor with a wide band gap and a preparation method thereof and an application in an organic solar cell with trisindene as the core. Background technique [0002] Solar energy has the characteristics of inexhaustibility, inexhaustibility, cleanness, no pollution, and no space limitation, and is an ideal renewable energy source. As one of the important forms of utilizing solar energy, solar cells have attracted much attention. Among them, as a typical representative of the third-generation solar cells, organic solar cells have become a research hotspot due to their advantages of light weight, flexibility, low cost, and large-area preparation. In recent years, the efficiency of bulk heterojunction organic solar cells has been greatly improved by synthesizing new donor and acceptor materials, optimizing the preparation process, and optimi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14H01L51/42H01L51/46
CPCY02E10/549
Inventor 彭强武文林张光军徐小鹏
Owner SICHUAN UNIV
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