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A photoelectric compound containing thiophene (selenophene) modification and its preparation method and application

A compound and 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: 2020-04-21
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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  • A photoelectric compound containing thiophene (selenophene) modification and its preparation method and application
  • A photoelectric compound containing thiophene (selenophene) modification and its preparation method and application
  • A photoelectric compound containing thiophene (selenophene) modification and its preparation method and application

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(Eonset red+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 mate...

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Abstract

The invention relates to a preparation method and application of a solution-processable organic photovoltaic compound using thiophene (selenophene) and thiophene (selenophene) as π bridges, and its structural formula is shown in formula I. On the basis of the π bridge, the compound of the present invention selects a suitable D and A unit organic photoelectric compound with low exciton binding energy and can effectively reduce the highest occupied electron orbital energy level of the molecule, allowing high-efficiency materials to obtain high open-circuit voltage become possible. The compound of the invention is used as the donor material of the active layer of the organic solar cell, and its highest open-circuit voltage exceeds 1V. Among them, the fluorinated acceptor unit is used as the terminal group, without any additives and heat and solvent annealing treatment, the battery energy conversion efficiency of its forward structure exceeds 10%, and the battery energy conversion efficiency of its inverted device structure reaches 11.5%. important 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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Patent Type & Authority Patents(China)
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
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