CN113004159A - Application of organic amine cation with hole transport performance in perovskite solar cell - Google Patents

Application of organic amine cation with hole transport performance in perovskite solar cell Download PDF

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CN113004159A
CN113004159A CN202110190751.4A CN202110190751A CN113004159A CN 113004159 A CN113004159 A CN 113004159A CN 202110190751 A CN202110190751 A CN 202110190751A CN 113004159 A CN113004159 A CN 113004159A
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organic amine
perovskite
amine cation
solar cell
hole transport
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王芳芳
秦天石
黄维
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Nanjing Shengyin Light Energy Co ltd
Nanjing Tech University
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Nanjing Shengyin Light Energy Co ltd
Nanjing Tech University
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Abstract

The invention designs and synthesizes a series of organic amine cations simultaneously provided with a high-carrier transmission unit and a low-dimensional perovskite construction unit, solves the problem of poor charge transmission performance between layers of the low-dimensional perovskite, and prepares the perovskite solar cell with high efficiency and high stability. The preparation process is simple, the raw materials are easy to obtain and low in cost, and the perovskite solar cell has a good prospect when being used as an interface material or a hole transport material.

Description

Application of organic amine cation with hole transport performance in perovskite solar cell
Technical Field
The invention belongs to the field of new solar cell materials, and particularly relates to application of organic amine cations with hole transport performance in a perovskite solar cell.
Background
The development of clean energy is the basis of low-carbon economy and sustainable development of the future human society, and the development of a low-cost and high-performance photoelectric conversion technology is one of the keys for realizing the goal. The metal halide perovskite has the advantages of organic and inorganic materials in the aspects of photoelectric property, solution process, low-temperature treatment and the like, and shows great application potential in the photovoltaic field. After a few years of development, the device efficiency of perovskite solar cells has broken through 25.2% [ National Renewable Energy Laboratory (NREL) efficacy chart, http: the material is similar to a thin film silicon cell, but the manufacturing cost is lower, so that the material becomes a novel photovoltaic system which is expected to further reduce the photovoltaic power generation price. In recent years, two-dimensional/three-dimensional mixed-dimension perovskite has received wide attention in the photovoltaic field due to its advantages of good photoelectric properties, high stability and the like, and is expected to realize a high-efficiency and stable perovskite photovoltaic device. Although the stability of the two-dimensional/three-dimensional mixed-dimension perovskite device is greatly improved, the efficiency of the device is still lower than that of a three-dimensional perovskite, mainly because the layered perovskite generally grows parallel to the substrate, the mobility of a large-size organic amine layer is low, and the charge transmission between perovskite layers is reduced similar to that of an insulating spacer between conductive inorganic layers, so that the improvement of the efficiency of the photovoltaic device is greatly influenced.
The invention designs and synthesizes a series of organic amine cations simultaneously provided with a high-carrier transmission unit and a low-dimensional perovskite construction unit, solves the problem of poor charge transmission performance between layers of the low-dimensional perovskite, and constructs the perovskite solar cell with high efficiency and high stability.
Disclosure of Invention
The invention provides an organic amine cation with hole transmission performance and application thereof. The organic amine cation is used for preparing perovskite solar cell
1. An organic amine cation having hole transport properties characterized by the following chemical structure I:
chemical structural formula I:
Figure RE-GSB0000193555020000011
n＝1，2，3；
in the formula, R1Is any one of chemical structural formulas II, R2＝I-，Br-，Cl-：
Chemical structural formula II:
Figure RE-GSB0000193555020000012
in the formula, R3Is any one of hydrocarbyloxy, hydrocarbylthio or chemical structural formula III;
chemical structural formula III:
Figure RE-GSB0000193555020000021
in the formula, R4Is hydrocarbyloxy or hydrocarbylthio
2. Organic amine cation with hole transport properties according to claim 1, characterized by being used as a hole transport layer or an interfacial layer for the production of perovskite solar cells.
The organic amine cation is applied to preparing the perovskite solar cell.
The device structure for preparing the perovskite solar cell by using the organic amine cation is as follows: the device structure is any one of the following four, a first device structure: a conductive glass substrate/an electron transport layer/a perovskite layer/an interface layer/a hole transport layer/a metal electrode formed by organic amine cation induction; second device structure: a conductive glass substrate/an electron transport layer/a perovskite layer/a hole transport layer/a metal electrode formed by organic amine cation induction; the third device structure: a conductive glass substrate/a hole transport layer/a perovskite layer/an interface layer/a perovskite layer/an electron transport layer/a metal electrode formed by organic amine cation induction; a fourth device structure: conductive glass substrate/perovskite layer/organic amine cation induced hole transport layer/perovskite layer/electron transport layer/metal electrode. The hole transport layer formed by the induction of organic amine cations and the interface layer formed by the induction of organic amine cations are prepared by adopting the series of organic amine cations with hole transport performance in claim 1.
Has the advantages that:
(1) the organic amine cation with the hole transport performance has simple preparation process and easily obtained raw materials, and is very suitable for industrial production.
(2) The organic amine cation with hole transmission performance can induce to form a low-dimensional perovskite structure, solves the problem of poor charge transmission performance between two-dimensional perovskite layers,
(3) the organic amine cation with the hole transport performance can realize a perovskite solar cell with the efficiency of more than 20 percent and has high stability. The organic amine cation of the invention is a hole transport material and an interface layer material with excellent performance.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the example serve to explain the invention and not to limit the invention.
FIG. 1 shows the structure of a perovskite solar cell device made with organic amine cations as the interface layer inducing material;
FIG. 2 is a graph comparing the external quantum efficiency versus wavelength curves of perovskite solar cells prepared from organic amine cations I of chemical structural formula I provided by the present invention with standard cells.
FIG. 3 is a graph comparing current and efficiency versus time curves for perovskite solar cells prepared from organic amine cations I of chemical structure I provided by the present invention with standard cells.
FIG. 4 is a graph comparing the efficiency distribution histograms of the perovskite solar cell prepared from the organic amine cation I of the chemical structural formula I provided by the present invention and the solar cell device of the standard cell.
FIG. 5 is a graph comparing the stability in ambient chamber of perovskite solar cells prepared with organic amine cation I of chemical structural formula I provided by the present invention with standard cells.
FIG. 6 is a nuclear magnetic hydrogen spectrum of organic amine cation I of chemical structural formula I in the present invention.
FIG. 7 is a nuclear magnetic carbon spectrum of the organic amine cation I of chemical structural formula I in the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. In addition, the technical features involved in the embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
Example 1: preparation of organic amine cation I with hole transport property
The synthetic route is as follows:
Figure RE-GSB0000193555020000031
wherein the synthesis of intermediate (1) is according to the reference: commun., 2020, 56, 7407-7410, intermediate (2) and the resulting nuclear magnetic hydrogen and carbon spectra of organic amine cation I are shown in fig. 6 and fig. 7.
Synthesis of intermediate (2) tert-butyl ((4 '- (bis (4-methoxyphenyl) amino) - [1, 1' biphenyl ] -4-yl) methyl) carbamate: under the protection of argon, 4-bromo-nitrogen, nitrogen-bis (4-methoxyphenyl) aniline (0.40g, 1.05mmol), 4- (tert-butoxycarbonyl) phenylboronic acid (0.25g, 1.00mmol) were added to a 100mL Schlenk's tube. Potassium carbonate (0.83g, 6.00mmol) was dissolved in a premixed 8mL (tetrahydrofuran: water ═ 5: 3 (v: v)) solution, and the solution was slowly poured into a reaction tube and stirred at room temperature for 20 minutes. Further, tetrakis (triphenylphosphine) palladium (0.11g, 0.10mmol) was added thereto, and the reaction was carried out at 65 ℃ for 10 hours. After the reaction was completed, the reaction solution was cooled to room temperature, the reaction solution was transferred to a separatory funnel with a small amount of dichloromethane, washed with water three times, and dried over anhydrous sodium sulfate for 20 minutes after collecting an organic phase. The solvent was removed by rotary evaporation and purified by column chromatography using the mobile phase (dichloromethane: petroleum ether 4: 1 (v: v)) and the product as a white solid (0.40g, 78%).
Nuclear magnetic data of intermediate (2):
1H NMR(400MHz，Chloroform-d)δ7.541(d，J＝8.4Hz，2H)，7.425(d，J＝8.8Hz，2H)，7.344(d，J＝8.4 Hz，2H)，7.121(d，J＝8.8Hz，4H)，7.012(d，J＝8.8Hz，2H)，6.877(d，J＝9.2Hz，4H)，4.860(s，1H)，4.356(s， 2H)，3.830(s，6H)，3.83(s，6H)，1.495(s，9H).
13C NMR(400MHz，Chloroform-d)δ156.00(d，J＝8.9Hz)，148.25，140.94，140.04，137.18，132.65， 128.03，127.53，126.74(d，J＝3.3Hz)，120.76，114.80，44.51，29.83，28.55，1.16.
synthesis of organic amine cation I (4 '- (bis (4-methoxyphenyl) amino) - [1, 1' biphenyl ] -4-yl) carboxamide bromate (TA-PMA): in a 50 mL round bottom flask, tert-butyl ((4 '- (bis (4-methoxyphenyl) amino) - [1, 1' biphenyl ] -4-yl (methyl) carbamate (0.21g, 0.50 mmol) was dissolved in 1mL dioxane, 15mL hydrobromic acid (48w/w) solution was slowly added dropwise at 0 deg.C, the reaction was maintained at 0 deg.C for 1 hour, after completion of the reaction, the reaction was dropped into a beaker containing 30mL ethyl acetate, and a precipitate appeared after standing at-20 deg.C for 10 hours.A Buchner funnel was used to filter and wash the filter cake with clean ethyl acetate to give the product as a white solid (0.18g, 73%).
Nuclear magnetic data of organic amine cation I:
1H NMR(400MHz，DMSO-d6)δ8.186(s，3H)，7.616(d，J＝8Hz，2H)，7.496-7.454(m，4H)，7.022(d，J＝ 9.2Hz，4H)，6.902(d，J＝8.8Hz，4H)，6.792(d，J＝8.8Hz，2H)，4.009(s，2H)，3.704(s，6H).
13C NMR(400MHz，Chloroform-d)δ155.93，148.16，141.19，140.97，132.79，127.68，127.52，126.71(d，J ＝3.9Hz)，120.79，114.78，77.48，77.17，76.85，55.59，46.18.
example 2: perovskite solar cell based on organic amine cation I
(1) Pretreatment of FTO conductive glass
The customized FTO glass is sequentially ultrasonically washed by glass detergent, deionized water (1 vol% in the deionized water), acetone and ethanol for 10 minutes respectively, dried by a nitrogen gun, placed in a glass watch glass, treated in ultraviolet-Ozone (UV-Ozone) for 20 minutes, and then conveyed to a nitrogen glove box for later use after the final organic residues are removed.
(2)SnO2Preparation of solution and preparation of film
SnO to be purchased2The colloidal dispersion was uniformly mixed with ultrapure water in a volume ratio of 1: 3, 35. mu.L of this solution was spin-coated on cleaned FTO glass at 3000 rpm for 30 seconds, annealed for 5 minutes, subjected to the second spin-coating, and immediately after this, placed on a hot stage at 150 ℃ and annealed for 30 minutes.
(3) Preparation of perovskite precursor and preparation of film
A mixture of 800uLN, N-dimethylformamide and dimethyl sulfoxide (v: v ═ 4: 1) was dissolved in 21.8mg of methylammonium bromide, 77.1mg of lead bromide, 548.0mg of lead iodide and 190.1mg of formamidine hydroiodide, and the solution was shaken on a shaker for 10 hours. 30 μ L of the solution was spin-coated on the previously prepared device at 6000 revolutions for 30 seconds, and 100 μ L of ethyl acetate was dropped on the surface of the perovskite 5 seconds before the completion of the spin-coating, and immediately after the completion, the perovskite was annealed on a hot stage at 100 ℃.
(4) Preparation of interface layer formed by organic amine cation induction
3mg of organic amine cation I was dissolved in 1mL of isopropanol solution, and the prepared solution was spin-coated on the surface of the perovskite layer at 3000 rpm for 30 seconds, and then placed on a hot stage at 100 ℃ for annealing for 10 minutes.
(5) Preparation of hole transport layer material and preparation of thin film
73mg of Spiro-OMeTAD was dissolved in 1mL of chlorobenzene, and then 18. mu.L of 520mg/mL Li-TFSI, 29. mu.L of 300mg/mL FK209 and 30. mu.L of 4-tert-butylpyridine were added thereto, and shaken well. 35 μ L of the prepared solution was spin-coated on the surface of HT2D layer at 3000 rpm for 30 seconds.
(6) Preparation of gold electrodes
The gold electrode is prepared by vacuum evaporation method, placing the prepared film into an evaporation cabin, and vacuumizing to less than 10%-4Pa, in
Figure RE-GSB0000193555020000042
Figure RE-GSB0000193555020000041
60nm of gold was evaporated.
Parameters of the perovskite solar cell device obtained according to the method are shown in table 1.
Table 1 device measurements of perovskite solar cells prepared using organic amine cation I
Battery device Voc[V] Jsc[mA/cm2] FF[％] PCE[％]
3D 1.15 21.95 73.41 18.53
1mg/mL of organic amine cation I 1.19 21.90 73.88 19.26
3mg/mL of organic amine cation I 1.21 22.81 75.08 20.71
5mg/mL of organic amine cation I 1.21 21.99 73.52 19.59
The applicant declares that the present invention illustrates the detailed structural features of the present invention through the above embodiments, but the present invention is not limited to the above detailed structural features, that is, it does not mean that the present invention must be implemented depending on the above detailed structural features. It should be understood by those skilled in the art that any modifications of the present invention, equivalent substitutions of selected components of the present invention, additions of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.

Claims (2)

1. An organic amine cation having hole transport properties characterized by the following chemical structure I:
chemical structural formula I:
Figure FSA0000233768200000011
in the formula, R1Is any one of chemical structural formulas II, R2＝I-，Br-，Cl-：
Chemical structural formula II:
Figure FSA0000233768200000012
Figure FSA0000233768200000013
in the formula, R3Is any one of hydrogen, oxyl, sulfenyl or a chemical structural formula III;
chemical structural formula III:
Figure FSA0000233768200000014
in the formula, R4Is hydrogen, hydrocarbyloxy or hydrocarbylthio.
2. Organic amine cation with hole transporting properties according to claim 1, characterized in that it is used in the preparation of perovskite solar cells.
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CN115028599A (en) * 2022-05-28 2022-09-09 福建师范大学 Hole crosslinking material and preparation method and application thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115028599A (en) * 2022-05-28 2022-09-09 福建师范大学 Hole crosslinking material and preparation method and application thereof
CN115028599B (en) * 2022-05-28 2023-09-15 福建师范大学 Hole crosslinking material and preparation method and application thereof

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