Preparation method and application of photovoltaic compound modified by thiophthene (benzoselenophene selenonaphthene)

A compound, optoelectronic technology, applied in the field of material chemistry, can solve the problem of few materials and achieve the effect of high open circuit voltage

Active Publication Date: 2018-03-06
嘉兴禾浦光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with polymer solar cells, solution-processable organic small molecule solar cells have developed rapidly in recent years because of the clear molecular structure and no molecular weight distribution, but there are only a few materials with an efficiency higher than 10%.

Method used

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  • Preparation method and application of photovoltaic compound modified by thiophthene (benzoselenophene selenonaphthene)
  • Preparation method and application of photovoltaic compound modified by thiophthene (benzoselenophene selenonaphthene)
  • Preparation method and application of photovoltaic compound modified by thiophthene (benzoselenophene selenonaphthene)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] Example 1: Synthesis of optoelectronic compounds M1, M2, M3 and M4.

[0109] A kind of organic photoelectric compound that is used for solar cell, the chemical structure of its compound is as shown in formula (I), and wherein several more specific structures are as follows:

[0110]

[0111] where X 1 =X 2 =X 3 =X 4 =S, R 2 =R 4 =C 6 h 13 , R 3 The specific structure after =H is as follows:

[0112]

[0113]

[0114] Preparation and synthesis of optoelectronic compound M1

[0115] It mainly includes the following steps:

[0116] ①Synthesis of π-bridge monomer 5-(5-bromo-6-hexyl[3,2-b]thiophen-2-yl)-4-hexylthiophene-2-carbaldehyde:

[0117]

[0118] ②Synthesis of intermediate dialdehyde terminal group and target compound M1

[0119]

[0120] ③Concrete steps for the synthesis of each compound:

[0121] Compound 3: Under nitrogen protection, Pb(PPh 3 ) 4 (5%mmol) was added to compound 1 (3g, 8.57mmol), compound 2 (2.5g, 9.12mmol), NaHCO 3 (...

Embodiment 3

[0136] Embodiment 3: Determination of the ultraviolet-visible absorption spectra of small molecules M1-M4 in chloroform solution and film state.

[0137] Dissolve an appropriate amount of M1 or M2 in chloroform to make a solution with a certain concentration, and take part of the solution and spin-coat it on a quartz plate to form a thin film of small molecules. The ultraviolet-visible absorption spectra of the compounds of M1-M4 measured in chloroform solution and film state are as follows: Figure 1-4 shown. It can be seen from the figure that M1-M4 has a wide absorption in the visible light region, and the film has a red shift of about 80nm relative to the solution, indicating that the two have a good aggregation effect in the film.

Embodiment 4

[0138] Embodiment 4: Determination of the cyclic voltammetry curve in the state of small molecule film

[0139] Figure 5 is based on the cyclic voltammograms of M1 and M2 films, Figure 6 Cyclic voltammograms based on M3 and M4 thin films. The chloroform solution was coated on the platinum electrode, and Ag / Ag+ was used as the reference electrode, and after drying to form a film, it was placed in the acetonitrile solution of tetrabutylammonium hexafluorophosphate for measurement. The onset oxidation potential and onset reduction potential obtained from the figure are then given by the formula E HOMO =-e(Eonset ox+4.71)(eV), ELUMO=-e(Eonsetred+4.71)(eV) Calculate the HOMO and LUMO energy levels of these two compounds. See Table 1 for specific values. It can be seen from the table that the four materials all have lower highest electron-occupied orbitals (HOMO), which provides a basis for obtaining high open circuits for photovoltaic devices prepared based on these two mater...

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Abstract

The invention relates to a preparation method and application of solution-processable organic photovoltaic compound with thiophthene (benzoselenophene selenonaphthene) and thiophene (selenophene) as pi-bridge. The structural formula of the compound is shown as the formula I. According to the compound, on the basis of the pi-bridge, appropriate D and A units are selected, and the organic photoelectric compound has low exciton binding energy and can effectively reduce the highest occupied electron orbit energy level of the molecule, which makes it possible that a high-efficiency material acquires high open circuit voltage. The compound is used as the donor material of the active layer of an organic solar battery, and the highest open circuit voltage is higher than 1 V. A fluorinated receptorunit is used as an end group, the compound is not subjected to any additive treatment or thermal and solvent annealing treatment, the battery energy conversion efficiency of the forward structure ismore than 10%, the battery energy conversion efficiency of the reverse element structure reaches 11.5%, and the compound has significant application value.

Description

technical field [0001] The invention belongs to the field of material chemistry, and in particular relates to a photoelectric compound containing thiophene (selenophene) and thiophene (selenophene) as π bridge modification and its preparation method and application. Background technique [0002] Solar cells are an inexhaustible source of clean energy - one of the most effective uses of solar energy. Compared with inorganic solar cells, organic solar cells have attracted extensive attention because of their advantages such as abundant raw materials, light weight, flexibility, foldability, and large-area printing process. Compared with polymer solar cells, solution-processable organic small molecule solar cells have developed rapidly in recent years because of the clear molecular structure and no molecular weight distribution, but there are only a few materials with an efficiency higher than 10%. [0003] Therefore, the design of the molecular structure to obtain a new type o...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07D495/04C07D517/04H01L51/46
CPCC07D495/04C07D517/04C07D519/00H10K85/655H10K85/656H10K85/654H10K85/6576H10K85/657Y02E10/549
Inventor邓丹魏志祥吕琨
Owner嘉兴禾浦光电科技有限公司