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Perovskite hole transport material based on triptycene mother nucleus and preparation method thereof

A hole-transporting material and perovskite technology, which is applied in semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc., can solve the problems of high synthesis cost of Spiro-MeOTAD, unfavorable commercial promotion, efficiency attenuation, etc., to achieve Excellent hole transport ability, good performance, and high thermal stability

Active Publication Date: 2018-10-16
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2011, Park et al [Nanoscale, 2011,3(10):4088-4093] increased the PCE to 6.5%, but after 10 minutes, the efficiency decayed by 80%
However, the high cost of Spiro-MeOTAD synthesis is not conducive to commercial promotion

Method used

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  • Perovskite hole transport material based on triptycene mother nucleus and preparation method thereof
  • Perovskite hole transport material based on triptycene mother nucleus and preparation method thereof
  • Perovskite hole transport material based on triptycene mother nucleus and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment one: 2,6,14-triptycene triiodide is synthesized

[0054]

[0055] (1) 2,6,14-Trinitrotriptycene 2

[0056] In a 250 mL two-necked flask, triptycene (5 g, 20 mmol) and concentrated nitric acid (65 wt%, 140 mL) were added. The mixed solution was heated to 70°C and reacted for 15 hours. After the reaction, the reaction solution was poured into 500 mL of ice water and stirred for half an hour. Then use a Buchner funnel to filter under reduced pressure, wash away the concentrated nitric acid with 1000 mL of ice water, and dry the filter cake to obtain a white solid. Dissolve the above solid in 50 mL of ethyl acetate, wash it twice with saturated brine, take the upper organic phase, add anhydrous magnesium sulfate to dry, filter, evaporate the solvent with a rotary evaporator, and then put it into the Vacuum oven overnight. The next day, the crude product was separated by chromatographic column with petroleum ether / ethyl acetate as eluent (3:1, v / v) to obtai...

Embodiment 2

[0061] Example 2: Synthesis of 4-bromo-N,N-bis(4-methoxyphenyl)aniline

[0062]

[0063] (1) 4-iodoanisole 6

[0064] In a 500mL double-necked flask, add 240mL methanol, 11.4mL concentrated sulfuric acid, ice bath for 15min, add anisole 5 (15mL, 0.14mol), and add potassium iodide (21.6g, 0.13mol) in 5 portions. Rise to room temperature, slowly add hydrogen peroxide aqueous solution (30wt%, 30mL) dropwise into the dropping funnel, raise the temperature to 55°C, stop the reaction after reacting overnight, cool to room temperature, extract with dichloromethane, and use 100mL saturated bisulfite Sodium wash twice. Add anhydrous sodium sulfate to the organic phase to dry, filter, and evaporate the solvent with a rotary evaporator. The crude product was recrystallized from methanol to obtain 6 as a white solid with a yield of 52%. Wherein the molar ratio of anisole: potassium iodide is 1:0.9. 1 H NMR (500MHz, CDCl 3 ) δ 7.56 (d, J = 8.9Hz, 2H), 6.68 (d, J = 8.9Hz, 2H), 3.78 ...

Embodiment 3

[0069] Example 3: Synthesis of 2-(tributyltin)-3,4-ethylenedioxythiophene

[0070]

[0071] Under nitrogen protection, 3,4-ethylenedioxythiophene 9 (4.0 g, 28.1 mmol) and dry tetrahydrofuran (100 mL) were added to a 250 mL Schlenk reaction flask. Nitrogen gas was continuously bubbled into the reaction solution, and it was cooled to -60°C. After 20 min, n-butyllithium solution (11.7 mL, 28.14 mmol, 2.4M n-hexane solution) was slowly added dropwise with a 20 mL syringe. After 2 hours, the dropwise addition was completed, and the temperature was continued for 15 minutes, and then slowly raised to room temperature. After stirring at room temperature for 2 h, the reaction solution was cooled to -60°C again, and after stirring for 20 min, tributyltin chloride (10 g, 31 mmol) was slowly added dropwise with a 20 mL syringe. Continue to stir at low temperature for 15 min after the dropwise addition, then slowly rise to room temperature, and stir overnight. The reaction was stoppe...

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Abstract

The present invention discloses a perovskite hole transport material based on a triptycene mother nucleus and a preparation method thereof. The material is 2,6,14-tri(50-(N,N-bi(4-methoxyphenyl)aminophenol-4-yl)-3,4-ethylenedioxythiophene-2-yl)-triptycene. The preparation method has the advantages of mild synthesis conditions, simple steps, cheap and easily obtained synthetic raw materials, and low synthesis costs. The prepared material has a good thermal stability, solubility and film forming property. An ultraviolet-visible light absorption spectrum indicates the hole transport material based on the triptycene mother nucleus has a large conjugate structure, has a more suitable HOMO level (-5.08 eV) than that of a mainstream hole transport material Spiro-MeOTAD, and provides a strong driving force for hole transporting. The carrier mobility of the material measured by a space charge limiting current method is 8x10<-4>cm<2>.V<-1>s<-1>. The perovskite hole transport material has potential.

Description

technical field [0001] The invention belongs to the field of perovskite solar cells, and in particular relates to a perovskite solar cell hole material containing a triptycene core and a preparation method thereof. Background technique [0002] Energy shortage has always restricted the development of the world economy, and a series of negative effects it has brought have become increasingly prominent. As a renewable green energy, solar energy is an effective strategy to solve this crisis. Since the first monocrystalline silicon solar cell was born in 1954, solar cells have developed rapidly, and many types of polycrystalline silicon thin-film cells, dye-sensitized cells, organic polymer cells, and perovskite cells have emerged. In particular, perovskite solar cells have attracted widespread attention from scientists due to their excellent carrier mobility and light absorption coefficient. In just 6 years, the photoelectric conversion efficiency (Power conversion efficiency...

Claims

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Application Information

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IPC IPC(8): C07D519/00H01L51/42H01L51/46
CPCC07D519/00H10K85/623H10K85/631H10K85/657H10K30/00Y02E10/549
Inventor 唐卫华孙宇浩尹新星俞江升赵德威
Owner NANJING UNIV OF SCI & TECH
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