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Square acid type organic small-molecular hole transport material and application thereof

A technology of hole transport materials and small molecules, applied in the field of squarylium organic small molecule hole transport materials, can solve the problems of unfavorable π-π stacking, small interaction force, unfavorable hole transport, etc., and achieve good stability , The synthesis process is simple, and the raw materials are cheap and easy to obtain

Pending Publication Date: 2021-11-09
HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently disclosed squarylium organic small molecule hole transport materials have asymmetric structures, but the intermolecular interaction force of asymmetric squarylium molecules is small, which is not conducive to the formation of π-π stacking and hole transport. Chemical additives need to be added during use, but the additives will affect the performance of the device

Method used

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  • Square acid type organic small-molecular hole transport material and application thereof
  • Square acid type organic small-molecular hole transport material and application thereof
  • Square acid type organic small-molecular hole transport material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A preparation method of squarylium organic small molecules, the reaction process is as follows, and the specific steps are as follows:

[0029]

[0030] (1) Add squaraine (11.4g) and thionyl chloride (21g) into a three-necked flask at a molar ratio of 1:2.1, add catalyst DMF, heat up to 50°C and reflux, and react under these conditions for 12 hours; then evaporate Remove thionyl chloride, add bromobenzene (21g) twice the amount of squaraine, and anhydrous aluminum chloride (8.5g) catalyst, heat up to 40°C, reflux for 12 hours; cool to room temperature after the reaction , and then the reaction solution was poured into ice water for quenching, and then extracted with dichloromethane; the extracted organic phase was dried with anhydrous magnesium sulfate, evaporated under reduced pressure, and then recrystallized with absolute ethanol to obtain compound 3.

[0031] (2) Add compound 3, 4-boronate-4', 4'-dimethoxytriphenylamine, lye and ethanol to the reaction solvent, c...

Embodiment 2

[0036]In a 100mL three-necked flask, add N,N-bis(4-methoxyphenyl)-[1,1'-biphenyl]-4-amine (152.5mg, 0.40mmol), squaraine (61.9mg, 0.21mmol), benzene: n-butanol = 1:1 (v / v) (60mL), connected to the water separator, heated at 80°C under the protection of N2, and refluxed for 22h. During the reaction, the color of the reaction solution gradually deepened and solids were precipitated. After the reaction was completed, it was cooled to room temperature, extracted, passed through a column, and recrystallized to obtain a squarylium organic small molecule—compound 6. The compound has a hole mobility of 1.9×10 -3 cm 2 V -1 the s -1 .

[0037]

experiment example 3

[0039] The squarylium organic small molecules synthesized in Examples 1 and 2—compound 5 and compound 6 were respectively used as hole transport materials in formal devices of perovskite solar cells, and their specific structures were FTO / c-TiO 2 / m-TiO 2 / Perovskite / HTM / Au, the schematic diagram of its structure is shown in Figure 4 As shown, using a xenon lamp solar simulator, the test light source intensity is AM1.5G (100mW cm -2 ) to test the photovoltaic performance of the prepared perovskite solar cell, the J-V curve of the device is as follows Figure 5 As shown, the PCE can reach up to 19.32% and 19.85%.

[0040] When the above squarylium small molecules are used as hole transport materials for perovskite solar cells, the device combination is not limited to the above examples, and other material layers in the device can be conventional solar cell materials.

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Abstract

The invention discloses a squaric acid type organic small-molecular hole transport material and application thereof, and relates to the technical field of photoelectric materials. The squaric acid type organic small-molecular hole transport material has a structural general formula as shown in the specification. The squaric acid type organic small-molecular hole transport material provided by the invention has relatively high hole mobility and photoelectric conversion efficiency, and can be used as a non-doped hole transport material; and a squaric acid micromolecule is simple in synthesis process, cheap and easily available in raw materials and good in stability, and can be used as a hole transport material of photoelectric devices such as perovskite solar cells, organic solar cells, organic light emitting diodes and field effect transistors.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a class of squarylium organic small molecule hole transport materials and applications thereof. Background technique [0002] In recent years, with the vigorous development of the optoelectronic industry, hole injection / transport materials have attracted extensive attention from researchers in many fields such as materials and physics, and have been successfully applied in organic-inorganic perovskite solar cells, organic solar cells, organic In optoelectronic devices such as light emitting diodes. [0003] An ideal hole injection / transport layer generally needs to have the following characteristics: high hole mobility, HOMO energy level matched with the photofunctional layer material to ensure effective injection and transport of holes at each interface, good Excellent air and heat stability, low production cost and good solvent and film-forming properties. [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/22H01L51/30H01L51/46H01L51/54
CPCC07C225/22C07C2601/04H10K85/631H10K10/46H10K30/10H10K30/00H10K50/15Y02E10/549
Inventor 孔凡太彭耀乐孙媛张近雪赵春蝶
Owner HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI