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D (A1-pi-A2) 2 type conjugated small molecule based on diaryl and indacene fused ring unit and preparation method of D (A1-pi-A2) 2 type conjugated small molecule

A small molecule, condensed ring technology, used in semiconductor/solid-state device manufacturing, electrical components, organic chemistry, etc., to achieve excellent near-infrared absorption performance, high short-circuit current, and improved sunlight utilization.

Active Publication Date: 2022-07-15
HUNAN INSTITUTE OF ENGINEERING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the reported near-infrared non-fullerene small-molecule acceptor materials all use A-D-A or A-π-D-π-A molecular construction strategies, and significant progress has been made. The PCE of related devices has exceeded 18%. unlimited potential

Method used

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  • D (A1-pi-A2) 2 type conjugated small molecule based on diaryl and indacene fused ring unit and preparation method of D (A1-pi-A2) 2 type conjugated small molecule
  • D (A1-pi-A2) 2 type conjugated small molecule based on diaryl and indacene fused ring unit and preparation method of D (A1-pi-A2) 2 type conjugated small molecule
  • D (A1-pi-A2) 2 type conjugated small molecule based on diaryl and indacene fused ring unit and preparation method of D (A1-pi-A2) 2 type conjugated small molecule

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Conjugated Small Molecule IDT (DPP-TDRCN) 2 Synthesis

[0044] The synthetic route and synthetic steps of this conjugated small molecule are as follows:

[0045]

[0046] 1. Synthesis of compound 2

[0047] In a 250mL there-necked flask, compound 1 (1.00g, 1.06mmol), 5-formyl-2-thiopheneboronic acid (0.51g, 2.12mmol), tetrakis (triphenylphosphine) palladium (25mg, 0.02mmol) were added successively, Sodium bicarbonate (0.53 g, 6.36 mmol) solution (15 mL distilled water) and 120 mL tetrahydrofuran. Under nitrogen protection, the reaction was refluxed at 85 °C for 24 h, the reaction was stopped, and the reaction was cooled to room temperature. The reaction solution was transferred to a separatory funnel, 50 mL of distilled water was added, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the organic solvent, and the obtained crude product was represented by petroleum ether (PE): dichlorom...

Embodiment 2

[0055] Conjugated Small Molecule IDT (TID-TDRCN) 2 Synthesis

[0056] The synthetic route and synthetic steps of this conjugated small molecule are as follows:

[0057]

[0058] 1. Synthesis of compound 8

[0059] In a 250mL three-necked flask, compound 7 (10g, 61.40mmol), 2-ethylhexylamine (11.9g, 92.10mmol), copper powder (0.20g, 3.08mmol), iodide (0.59g, 3.08g) were added successively mmol), potassium phosphate (26.06 g, 122.80 mmol), N,N-dimethylethanolamine (120 mL), under nitrogen protection, the reaction was stirred at 80° C. for 48 h. The reaction was stopped, cooled, and filtered with suction. The obtained filtrate was subjected to rotary distillation under reduced pressure to remove the solvent, and the residue was distilled under reduced pressure to obtain compound 8 (5.2 g, 40%) as a brownish-yellow liquid. 1 H NMR (400MHz, CDCl 3 )δ: 7.18(dd, 1H), 6.65(dd, 1H), 5.95(s, 1H), 3.61(s, 1H), 3.01(d, 2H), 1.63(m, 1H), 1.30-1.35(m ,8H),0.92(m,6H).

[0060] 2. Sy...

experiment example 3

[0075] Conjugated small molecule IDT (DPP-TDRCN) prepared in Example 1 2 and the IDT (TID-TDRCN) prepared in Example 2 2 Performance characterization:

[0076] of the synthesized compounds 1 H NMR spectrum was determined by Bruker Dex-300 NMR or 400NMR instrument; mass spectrum (MS) was obtained by analyzing and testing the MALDI-TOF mass spectrometer of Bruker Bifiex; thermogravimetric (TGA) curve was obtained by thermal analyzer (model Perking-El TGA), tested at a heating rate of 20 °C / min; differential scanning calorimetry (DSC) curve was tested by TA DSCQ10 analyzer, under nitrogen atmosphere, tested at a heating rate of 20 °C / min; UV-Vis absorption spectrum by Shimadzu UV-800 UV-Vis spectrophotometer was used to measure; the cyclic voltammetry curve was measured by CHI630E electrochemical analyzer.

[0077] 1. Conjugated small molecule IDT (DPP-TDRCN) 2 and IDT (TID-TDRCN) 2 Thermal Stability Determination of

[0078] figure 1 and figure 2 Shown are the conjugate...

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Abstract

The invention relates to a D (A1-pi-A2) 2 type conjugated small molecule based on a diaryl and indacene fused ring unit and a preparation method thereof. According to the conjugated micromolecule, a series of narrow-band-gap micromolecule photoactive layer materials capable of absorbing near-infrared light are constructed by selecting and matching electron withdrawing groups A1 and A2 with different properties by taking a diaryl group with a rigid plane structure and a fused ring as an electron donating (D) unit and thiophene as a pi bridge unit. The material has good solubility, near-infrared light absorption capability and proper energy level; meanwhile, the material has a more ordered intermolecular stacking state and an ultra-narrow band gap spectrum, more sunlight can be absorbed, and high short-circuit current can be obtained. The material can become an electron donor or an electron acceptor material in a photoactive layer by adjusting the electron withdrawing characteristic of the binary acceptor unit, is suitable for being used as the electron donor or the electron acceptor material, and has good popularization and application prospects.

Description

technical field [0001] The invention relates to the technical field of organic photovoltaics, in particular to a D(A 1 -π-A 2 ) 2 Type conjugated small molecules and preparation methods thereof. Background technique [0002] Organic photovoltaic cells have received extensive attention from researchers around the world due to their low cost, light weight, and the ability to be fabricated into large-area flexible devices from solution. In the past two decades, fullerene derivatives (such as PC 61 BM, PC 71 BM, etc.) have been widely used as electron acceptor materials due to their advantages such as large electron affinity, high electron mobility, and isotropic electron transport capability, achieving device photoelectric conversion efficiency (PCE) as high as 11%. ) (eg Nat. Energy, 2016, 1:15027), which has played a pivotal role in the rapid development of organic photovoltaic cells. However, the defects of such materials themselves, such as high preparation and purifi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/46H01L51/42
CPCC07D519/00H10K85/6576H10K85/6572H10K85/657H10K30/00
Inventor 彭文红吴涛邓继勇陶强张伟杰颜东匡纪炜
Owner HUNAN INSTITUTE OF ENGINEERING
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