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CN-121974952-A - Dibenzofuran-carbazolyl compound, preparation method thereof and trans-perovskite solar cell

CN121974952ACN 121974952 ACN121974952 ACN 121974952ACN-121974952-A

Abstract

The invention discloses a dibenzofuran-carbazolyl compound, a preparation method thereof and a trans-perovskite solar cell, belonging to the technical field of perovskite solar cells, the core molecular structure of the dibenzofuran-carbazolyl compound provided by the invention is based on a dibenzofuran-carbazole condensed or connected skeleton, and multifunctional integration is realized by introducing phosphorus oxygen groups. In the aspect of energy level matching, the condensed ring system has higher highest occupied molecular orbit energy level, can realize more optimized energy level alignment with the valence band top of the perovskite light absorption layer, and effectively reduces the interface barrier of hole extraction, thereby being beneficial to improving the open circuit voltage of the device.

Inventors

  • DING YE
  • ZHAO JIARUI
  • YANG HUSHENG

Assignees

  • 中茂绿能科技(西安)有限公司

Dates

Publication Date
20260505
Application Date
20260206

Claims (10)

  1. 1. A dibenzofuran-carbazolyl compound is characterized in that the structural general formula of the dibenzofuran-carbazolyl compound is as follows: Or (b) ; Wherein each L 1 、L 2 、L 3 is independently C 0 ～C 4 alkylene.
  2. 2. The dibenzofuran-carbazolyl compound of claim 1, characterized in that each L 1 、L 2 、L 3 is independently a linear alkylene of C 1 ～C 4 .
  3. 3. The dibenzofuran-carbazolyl compound according to claim 1, characterized in that it is any one of the following structural formulas: 、 、 、 。
  4. 4. a process for the preparation of a dibenzofuran-carbazolyl compound according to claim 1 comprising the steps of: The method comprises the steps of dissolving a compound of a formula 3 and a compound of a formula 4 as raw materials in an organic solvent at room temperature, carrying out a coupling reaction under the action of alkali and a catalyst, connecting carbazole on dibenzofuran to obtain a compound of a formula 5, carrying out a reflux reaction at 130-160 ℃ by using the compound of the formula 5 and a lipid compound as raw materials to obtain a compound of a formula 6, carrying out a substitution reaction at room temperature in the organic solvent by using the compound of the formula 6 and trimethyl bromosilane of the formula 7 as raw materials, and carrying out a hydrolysis reaction in a methanol aqueous solution to obtain a dibenzofuran-carbazolyl compound of the formula 1, wherein the synthetic route of the dibenzofuran-carbazolyl compound of the formula 1 is as follows: ; Or the compound of formula 8 and the compound of formula 4 are taken as raw materials, dissolved in an organic solvent at room temperature, subjected to coupling reaction under the action of alkali and a catalyst, and connected with carbazole to obtain the compound of formula 9, the compound of formula 9 and the lipid compound are taken as raw materials, and subjected to reflux reaction at 130-160 ℃ to obtain the compound of formula 10, the compound of formula 10 and the trimethyl bromosilane of formula 7 are taken as raw materials, subjected to substitution reaction in the organic solvent at room temperature, and subjected to hydrolysis reaction in a methanol aqueous solution to obtain the dibenzofuran-carbazolyl compound of formula 2, wherein the synthetic route of the dibenzofuran-carbazolyl compound of formula 2 is as follows: ; Wherein each L 1 、L 2 、L 3 is independently C 0 ～C 4 alkylene.
  5. 5. The method for producing a dibenzofuran-carbazolyl compound according to claim 4, wherein the molar ratio of said compound of formula 3 to said compound of formula 4 is 1:2 to 10, and the molar ratio of said compound of formula 8 to said compound of formula 4 is 1:2 to 10.
  6. 6. The method for producing a dibenzofuran-carbazolyl compound according to claim 4, wherein the molar ratio of the compound of formula 5 to the lipid compound is 1:2 to 5, and the molar ratio of the compound of formula 9 to the lipid compound is 1:2 to 5.
  7. 7. The method for producing a dibenzofuran-carbazolyl compound according to claim 4, wherein the molar ratio of the compound of formula 6 to the trimethylbromosilane of formula 7 is 1:2 to 5, and the molar ratio of the compound of formula 10 to the trimethylbromosilane of formula 7 is 1:2 to 5.
  8. 8. The process for producing a dibenzofuran-carbazolyl compound according to claim 4, wherein said lipid compound is selected from diethyl 2-bromoethylphosphonate and triethyl phosphite, and said organic solvent is 1, 4-dioxane.
  9. 9. A trans-perovskite solar cell comprising a conductive substrate, a hole transport layer, a perovskite light absorption layer, an electron transport layer and a metal electrode sequentially arranged from bottom to top, wherein the hole transport layer is formed by using the dibenzofuran-carbazolyl compound as described in claim 1 or 2 as a self-assembled monolayer material.
  10. 10. The trans-perovskite solar cell according to claim 9, wherein the hole transport layer is prepared by dissolving dibenzofuran-carbazolyl compound in ethanol under nitrogen atmosphere to obtain a coating solution with a concentration of 0.5 mg/mL-6 mg/mL, spin-coating the coating solution on a conductive substrate at 1000 rpm-5000 rpm, and annealing at 100 ℃ to 150 ℃.

Description

Dibenzofuran-carbazolyl compound, preparation method thereof and trans-perovskite solar cell Technical Field The invention relates to the technical field of perovskite solar cells, in particular to a dibenzofuran-carbazolyl compound, a preparation method thereof and a trans-perovskite solar cell. Background Perovskite solar cells have the outstanding advantages of low preparation cost, high photoelectric conversion efficiency, flexibility and the like, and become a research hotspot in the photovoltaic field. Up to now, the photoelectric conversion efficiency of laboratory-grade perovskite solar cells has broken through 27%, and has demonstrated great commercialization potential. However, the problems of poor long-term stability, serious interface charge recombination and the like still limit the core bottleneck of large-scale application. The self-assembled monomolecular film (SAM) is used as a key material of a cavity selection layer in the perovskite solar cell, and can form an ordered film on the surface of a Transparent Conductive Oxide (TCO) substrate through intermolecular and intermolecular interactions, so that the photo-generated holes can be extracted efficiently, the work function of the substrate can be adjusted downwards, interface defects can be passivated, the substrate is blocked from being in direct contact with the perovskite layer, and the efficiency and the stability of the cell are improved. At present, a SAM material for a perovskite battery mainly uses carbazole derivatives, and although carbazole compounds have strong electron donating ability and a large pi conjugated system, the existing carbazole SAM material generally has the defects of loose molecular stacking, uneven coverage and weak solvent desorption resistance, and easily falls off molecules in a high-temperature and high-humidity environment, so that a substrate is exposed and decomposition of a perovskite layer is accelerated, and the efficiency of the battery is seriously attenuated under severe conditions. Disclosure of Invention The invention provides a dibenzofuran-carbazolyl compound, a preparation method and a trans-perovskite solar cell, which effectively solve the technical problems of serious efficiency attenuation of the cell under high-temperature and high-humidity environments caused by loose molecular stacking, uneven coverage and weak solvent desorption resistance of the existing carbazole SAM material, and simultaneously provide an indolocarbazole compound for a hole transport layer material of the perovskite solar cell, thereby effectively improving the hole mobility, filling factor and photoelectric conversion efficiency of the inverted perovskite solar cell. The first object of the present invention is to provide a dibenzofuran-carbazolyl compound having the structural general formula: Or (b) Wherein each L 1、L2、L3 is independently C 0～C4 alkylene. As a preferred embodiment, each of said L 1、L2、L3 is independently a C 1～C4 linear alkylene group. As a preferred embodiment, the dibenzofuran-carbazolyl compound is any one of the following structural formulas:、、、。 The second object of the present invention is to provide a method for preparing the dibenzofuran-carbazolyl compound, comprising the steps of: The method comprises the steps of dissolving a compound of a formula 3 and a compound of a formula 4 as raw materials in an organic solvent at room temperature, carrying out a coupling reaction under the action of alkali and a catalyst, connecting carbazole on dibenzofuran to obtain a compound of a formula 5, carrying out a reflux reaction at 130-160 ℃ by using the compound of the formula 5 and a lipid compound as raw materials to obtain a compound of a formula 6, carrying out a substitution reaction at room temperature in the organic solvent by using the compound of the formula 6 and trimethyl bromosilane of the formula 7 as raw materials, and carrying out a hydrolysis reaction in a methanol aqueous solution to obtain a dibenzofuran-carbazolyl compound of the formula 1, wherein the synthetic route of the dibenzofuran-carbazolyl compound of the formula 1 is as follows: 。 Or the compound of formula 8 and the compound of formula 4 are taken as raw materials, dissolved in an organic solvent at room temperature, subjected to coupling reaction under the action of alkali and a catalyst, and connected with carbazole to obtain the compound of formula 9, the compound of formula 9 and the lipid compound are taken as raw materials, and subjected to reflux reaction at 130-160 ℃ to obtain the compound of formula 10, the compound of formula 10 and the trimethyl bromosilane of formula 7 are taken as raw materials, subjected to substitution reaction in the organic solvent at room temperature, and subjected to hydrolysis reaction in a methanol aqueous solution to obtain the dibenzofuran-carbazolyl compound of formula 2, wherein the synthetic route of the dibenzofuran-carbazolyl compound of formula 2 is as follows: Wherein e