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Hole transporting material with indacenodithiophene as core, synthesis method thereof and application thereof

A technology of hole transport material and dithiophene, which is applied in photovoltaic power generation, electrical components, climate sustainability, etc., can solve the problems of complex synthesis and purification steps, increase the cost of battery production, limit practicality, etc., and achieve thermal stability And the effect of good chemical stability, improved photoelectric performance, and adjustable energy level

Inactive Publication Date: 2019-11-26
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the classic hole transport material is the organic small molecule hole transport material 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'- Spiro-bifluorene (Spiro-OMeTAD), however, due to its complicated synthesis and purification steps, makes its market price as high as 1500 yuan / gram, which greatly increases the production cost of the battery and limits its practicability in industrial production

Method used

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  • Hole transporting material with indacenodithiophene as core, synthesis method thereof and application thereof
  • Hole transporting material with indacenodithiophene as core, synthesis method thereof and application thereof
  • Hole transporting material with indacenodithiophene as core, synthesis method thereof and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of hole transport material IDT1:

[0039]

[0040] (i) Add 4,4,9,9-tetrakis(4-n-hexylphenyl)indaeodithiophene derivative (0.725g, 0.8mmol) and solvent tetrahydrofuran THF (30mL) into a dry reaction vessel, Fix the reaction vessel on an iron stand, and stir in an ice-water bath. While stirring, add N-bromosuccinimide (NBS, 0.285g, 1.6mmol) in small amounts, react for 2 hours, and then warm up to room temperature , reacted for 6h, after the reaction was over, added an aqueous solution (100mL) to the reaction solution, extracted three times with dichloromethane (150mL), collected the organic layer, removed the organic solvent under reduced pressure, and separated the resulting solid with a silica gel column. , petroleum ether as the eluent, and vacuum-dried to obtain white solid compound 1 (0.809 g, yield 95.2%). 1 H NMR (400MHz, Chloroform-d) δ7.35(s,2H),7.10(q,J=8.4Hz,16H),7.01(s,2H),2.58(t,J=7.8Hz,8H),1.58 (s,8H),1.40–1.27(m,24H),0.96–0.85(m,12H).

[004...

example 2

[0045] Synthesis of hole transport material IDT2:

[0046]

[0047] (i) Add 4,4,9,9-tetra-n-hexylindaprodithiophene derivatives (0.482g, 0.8mmol) and solvent tetrahydrofuran THF (30mL) into a dry reaction vessel, and fix the reaction vessel on an iron Stand on the stand, and stir in an ice-water bath, while stirring, add N-bromosuccinimide (NBS, 0.285g, 1.6mmol) in small amounts, react for 1.5h, warm up to room temperature, react for 5h, react After the end, add aqueous solution (100mL) to the reaction solution, extract three times with dichloromethane (150mL), collect the organic layer, remove the organic solvent under reduced pressure, separate the obtained solid with a silica gel column, and use petroleum ether as the washing agent. The solvent was removed and dried in vacuo to obtain white solid compound 1 (0.583 g, yield 96.1%). 1 H NMR (400MHz, Chloroform-d) δ7.20(s,2H),6.99(s,2H),1.90(dddd,J=43.9,13.3,11.6,4.8Hz,8H),1.20–1.07(m,24H ),0.81(t,J=6.9Hz,20H).

[0048] ...

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Abstract

The invention belongs to the field of organic semiconductor functional materials and relates to a hole transporting material with indacenodithiophene as a core, a synthesis method thereof and an application thereof in perovskite solar cells. The invention takes the indacenodithiophene group as the core structure, and the two ends are connected with N, N-dimethoxytriphenylamine, and different sidechain groups are introduced into the core structure, the molecular configuration of the material and the way of molecular accumulation are adjusted, and then different material properties are obtained. The hole transporting material synthesized by the invention has the advantages of simple synthesis, adjustable energy level, high hole mobility and conductivity, good thermal stability and chemicalstability, and the like. When the hole transporting material is applied to a perovskite solar cell, the photoelectric conversion efficiency is improved, the device stability is enhanced, and the device preparation cost is reduced.

Description

technical field [0001] The invention belongs to the field of organic semiconductor functional materials, and relates to a hole-transporting material with indanodithiophene as the core, a synthesis method thereof, and an application in perovskite solar cells. Background technique [0002] In the past ten years, organic-inorganic hybrid perovskite solar cells (Perovskite Solar Cells, PSCs) have attracted extensive attention from researchers due to their advantages of low cost, high efficiency, and simple preparation process, and have become a research field. One of the research hotspots. [0003] At present, the photoelectric conversion efficiency of perovskite solar cells has rapidly increased from the initial 3% to 24.2%. High-efficiency perovskite solar cell devices require a good stack structure, which is mainly composed of perovskite absorption layer, hole transport layer, electron transport layer and electrodes. Under light, the perovskite absorption layer in the batte...

Claims

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Application Information

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IPC IPC(8): C07D495/04H01L51/42H01L51/46
CPCC07D495/04H10K85/6576H10K30/152H10K30/151Y02E10/549Y02P70/50
Inventor 陈承吴成程明陶力
Owner JIANGSU UNIV
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