CN116253694A - Ligand, metal organic framework material, application of ligand and metal organic framework material and perovskite solar cell - Google Patents
Ligand, metal organic framework material, application of ligand and metal organic framework material and perovskite solar cell Download PDFInfo
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Abstract
Ligand, metal organic framework material, application of ligand and metal organic framework material and perovskite solar cell. The invention relates to the technical field of photovoltaic materials, and solves the problem of poor stability of the existing perovskite solar cell. The metal organic frame material is prepared by using a ligand for preparing the metal organic frame material, and the composition molecular formula of the metal organic frame material is Tb 3 (L) 2 Wherein L is C 14 H 12 N 6 O 2 . And also (3) the methodThere is provided the use of a metal organic framework material as above in a perovskite solar cell. The perovskite solar cell comprises a conductive glass substrate, an electron transport layer, a perovskite absorption layer, a hole transport layer and a metal electrode, wherein the hole transport layer comprises the metal organic framework material.
Description
Technical Field
The invention relates to the technical field of photovoltaic materials, in particular to a ligand, a metal organic framework material, application of the ligand and the metal organic framework material and a perovskite solar cell.
Background
In recent years, the rapid development of social economy consumes a large amount of fossil energy, which causes shortage of fossil energy and the accompanying environmental pollution problem is also becoming serious, and clean green energy, such as renewable resources of solar energy, wind energy and the like, is actively sought all over the world. The solar energy is taken as one of renewable energy sources, is green and environment-friendly, has important influence on long-term energy strategy, and thus research on solar energy utilization is increased in various countries of the world. In order to effectively utilize solar energy, more and more people begin to aim at developing a novel solar cell with high efficiency and low cost, and among the novel solar cells, perovskite solar cells are outstanding by virtue of the advantages of high device efficiency, high light absorption coefficient and the like, and become important research contents in the field of novel solar cells.
Perovskite solar cells are solar cells that utilize perovskite-type organometallic halide semiconductors as light absorbing materials, and mainly include conductive glass, an electron transport layer, a perovskite layer, a hole transport layer, and a back electrode. The hole transport layer plays roles in extracting and transporting hole carriers in the solar cell, so that the selection of a proper hole transport material is important for realizing an efficient and stable perovskite solar cell.
In the hole transport materials commonly used at present, 2', 7' -tetrakis [ N, N-bis (4-methoxyphenyl) amino group]The conductivity and hole extraction efficiency of the 9,9' -spirobifluorene (Spiro-OMeTAD) are low, 4-Tertiary Butyl Pyridine (TBP) and lithium bis (trifluoromethanesulfonyl) imide (LI-TFSI) are required to be added, and the oxidation of the Spiro-OMeTAD into the Spiro-OMeTAD with higher conductivity and hole migration efficiency is promoted + Thereby increasing the photoelectric performance of the battery. However, the TBP and the LI-TFSI can be used after a certain time of dry air oxidation in the actual use process, and the air oxidation process is not controlled, and the LI-TFSI and the TBP are simultaneouslyMoisture in the air is easy to absorb to deliquesce, so that decomposition of perovskite is accelerated, and stability of battery performance is affected. Therefore, development of an additive for replacing air to directly oxidize Spiro-OMeTAD has become an important research topic.
Disclosure of Invention
In order to solve the problem of poor stability of the existing perovskite solar cell, the invention provides a ligand, a metal organic framework material, application of the ligand and the metal organic framework material, and the perovskite solar cell.
The technical scheme of the invention is as follows:
a ligand for preparing metal organic frame material has the following structural formula:
the metal organic frame material is prepared by using the ligand for preparing the metal organic frame material, and the composition molecular formula of the metal organic frame material is Tb 3 (L) 2 Wherein L is C 14 H 12 N 6 O 2 The structure of L is identical to the ligand structure described above.
Use of a metal organic framework material as described above in a perovskite solar cell.
A perovskite solar cell comprising a conductive glass substrate, an electron transport layer, a perovskite absorber layer, a hole transport layer comprising a metal organic framework material as described above, and a metal electrode.
Compared with the prior art, the invention has the following specific beneficial effects:
the invention solves the problem that the oxidation process of the Spiro-OMeTAD air in the prior battery hole transport material affects the stability of the battery performance, and provides an organic ligand which is applied to the synthesis of metal organic frame material MOF-ET 23; the synthesized MOF-ET23 is used as a hole transport layer additive, so that the defect of a thin film crystal boundary can be reduced, the charge transport in the battery is accelerated, the charge recombination is inhibited, and the photoelectric performance of the perovskite solar cell is optimized; the prepared perovskite solar cell has good photoelectric conversion efficiency, and is a conductive system with most excellent performance reported in the prior art.
Drawings
FIG. 1 is a schematic diagram of a synthetic route for preparing ligands for metal organic framework materials according to the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of intermediate 1 prepared in the examples;
FIG. 3 is a carbon spectrum of intermediate 1 prepared in the examples;
FIG. 4 is a mass spectrum of intermediate 1 prepared in the examples;
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of the ligand prepared in the example;
FIG. 6 is a carbon spectrum of the ligand prepared in the examples;
FIG. 7 is a mass spectrum of the ligand prepared in the example;
FIG. 8 is a schematic diagram of the structural composition of a perovskite solar cell according to the present invention;
FIG. 9 is a graph of electrochemical impedance characteristics of a perovskite solar cell according to the invention;
fig. 10 is a J-V plot of a perovskite solar cell according to the invention.
Detailed Description
In order to make the technical solution of the present invention clearer, the technical solution of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings of the present invention, and it should be noted that the following embodiments are only used for better understanding of the technical solution of the present invention, and should not be construed as limiting the present invention.
The synthetic route for preparing the ligand for the metal organic framework material in the embodiment is shown in the attached figure 1 of the specification. Wherein, the 2-amino-4-bromoxynil (CAS: 304858-65-9) and the 3-amino-4-boron benzoic acid (CAS: 116378-39-3) are all obtained by direct purchase from the market.
First step, synthesis of intermediate 1:
to 100mL of 1, 4-dioxane containing 2-amino-4-bromoxynil (3.3 g,17 mmol) was added 30mL of an ethanol solution containing 3-amino-4-boracic acid (4.52 g,25 mmol), followed by addition of potassium carbonate (17.39 g,0.125 mmol) and 100mL of deionized water, the reaction mixture was degassed with argon for 20min, tetrakis (triphenylphosphine) palladium (0.589 g,0.51 mmol) was added, the reaction system was placed in an oil bath, stirred at 85℃for 24h, and slowly cooled to 25℃after the completion of the reaction; then adding 100mL of deionized water, stirring at room temperature for reaction for 1h, and filtering to remove insoluble matters; the solution was treated with 2mol/L hydrochloric acid and stirred to give a white precipitate, the solid was collected by filtration, washed thoroughly with 300mL of deionized water, and dried under reduced pressure at 60℃to give 4.94g of a white solid, intermediate 1, in 78% yield.
And (3) performing nuclear magnetic resonance hydrogen spectrum analysis, carbon spectrum analysis, mass spectrum analysis and element analysis test on the obtained intermediate 1 respectively.
The nuclear magnetic resonance hydrogen spectrum is shown in fig. 2, and the result is as follows:
1 HNMR(400MHz，DMSO)：
δ8.07(d，1H)，7.78(d，1H)，7.73(d，1H)，7.57(d，1H)，7.51(d，1H)，7.26(d，1H)，6.28(d，1H)，5.93(s，2H)，5.40(d，1H)；
the carbon spectrum is shown in fig. 3, and the characteristic result of the carbon spectrum is as follows:
13 CNMR(100MHz，DMSO)：
δ167.22，148.42，147.74，140.31，134.41，133.60，130.52，128.10，125.69，125.37，117.35，117.07，115.56，95.23；
the mass spectrum is shown in fig. 4, and the mass spectrum characterization result is as follows:
ESI(m/z)：[M+H] + Calcd.for C 14 H 11 N 3 O 2 ，253.26；Found，254.07；
elemental analysis test results:
Calcd.for C 14 H 11 N 3 O 2 ，C，66.40，H，4.38，N，16.59，O，12.63；Found，C，65.75，H，5.21，N，17.09，O，11.54。
from the above analysis data, it can be demonstrated that the intermediate 1 obtained has the structural formula:
secondly, synthesizing a ligand:
to a three-necked flask, intermediate 1 (2.27 g,8.95 mmol), sodium azide (1.5 g,23.07 mmol), ammonium chloride (1.24 g,23.1 mmol) and 40mLN, N-dimethylformamide were added, and the reaction mixture was stirred at 120℃for 72 hours, cooled to 25℃after the completion of the reaction, poured into 300mL of deionized water, and the solid was collected by filtration, washed with 150mL of deionized water and dried under reduced pressure at 60℃to give 2.09g of a white solid in 79% yield.
And respectively performing nuclear magnetic resonance hydrogen spectrum analysis, carbon spectrum analysis, mass spectrum analysis and element analysis test on the obtained ligand, wherein the results are as follows:
the nuclear magnetic resonance hydrogen spectrum is shown in fig. 5, and the result is as follows:
1 HNMR(400MHz，DMSO)：δ8.07(d，1H)，7.77(d，2H)，7.58(d，1H)，7.51(d，1H)，7.04(d，1H)，6.58(d，1H)，6.28(d，1H)，5.70(d，1H)，5.40(d，1H)；
the carbon spectrum is shown in FIG. 6, and the results are as follows:
13 CNMR(100MHz，DMSO)：δ167.22，160.23，147.74，144.56，136.99，134.41，130.52，128.10，126.89，125.69，122.66，119.51，115.56，111.66；
the mass spectrum is shown in fig. 7, and the result is as follows:
ESI(m/z)：[M+H] + Calcd.for C 14 H 12 N 6 O 2 ，296.29；Found，297.02；
elemental analysis test results:
Calcd.for C 14 H 12 N 6 O 2 ，C，56.75，H，4.08，N，28.36，O，10.80；Found，C，56.13，H，4.87，N，27.64，O，11.02。
from the above analytical data, it can be demonstrated that the resulting ligand has the structural formula:
thirdly, synthesizing MOF-ET 23:
ligand (25.77 mg,0.087 mmol), tb (NO 3 ) 3 ·6H 2 O (18.92 mg,0.0435 mmol), 2-fluorobenzoic acid (24.37 mg,0.174 mmol), 1mLN, N-dimethylformamide and 1.5mL ethanol were placed in a three-necked flask, then heated at 115℃for 96 hours, after the completion of the reaction, cooled slowly to 25℃and then washed with N, N-dimethylformamide and ethanol and dried to give MOF-ET23.
Characterization of the metal organic framework material MOF-ET 23:
the synthesized MOF-ET23 crystal is stored in a glass capillary, the crystal structure is tested by adopting single crystal X-rays, the instrument is a Bruker-Apex II type CCD detector, a CuK alpha (lambda= 1.54178A) X-ray source is used for collecting, the data is SADABS program for correcting absorption, and extinction or decay is not corrected. Directly solving by using a SHELXTL software package, and obtaining a test result shown in a table 1;
TABLE 1
Fourth, preparing a perovskite solar cell:
(1) Preparation of a conductive glass substrate: fluorine doped tin oxide (FTO) glass was etched with zinc powder and 3mol/L hydrochloric acid, then washed sequentially with detergent, deionized water, acetone and ethanol, and the glass was washed with ozone for 20min before spin coating with titanium dioxide.
(2) Electron transport layer: 2.5mL of isopropanol is respectively added into two 5mL solvent bottles, 350 mu L of titanium isopropoxide and 35 mu L of 3mol/L hydrochloric acid are respectively and slowly added dropwise into the two bottles, under the stirring condition, the solution is slowly added dropwise into the solvent bottle containing titanium isopropoxide by using the solvent bottle containing hydrochloric acid, and the solution is stirred at room temperature for 30min to obtain a compact layer solution; transferring a proper amount of compact layer solution, simply spin-coating the compact layer solution onto an FTO substrate at a rotating speed of 3000rpm, calcining the compact layer solution in a baking oven at 70 ℃ for 10min, transferring the compact layer solution into a muffle furnace, and calcining the compact layer solution at 500 ℃ for 30min; the titanium dioxide slurry was then prepared according to 1: and diluting and uniformly stirring the substrate in absolute ethyl alcohol according to the mass ratio of 7, transferring a certain volume of slurry diluted solution, dripping the slurry diluted solution onto a compact layer substrate, spin-coating the substrate at the speed of 4000rpm for 45s, placing the spin-coated substrate into a muffle furnace, heating to 500 ℃ and calcining for 30min to obtain the FTO/electron transport layer.
(3) Preparation of perovskite absorption layer: 1mol/L of iodinated formamide, 0.2mol/L of methyl amine bromide (MABr), 0.2mol/L of lead bromide (PbBr) 2 ) And 1.1mol/L lead iodide in 1mLN, N-dimethylformamide and dimethyl sulfoxide (volume ratio 4: 1) Mixing in a solvent of (2) to prepare a perovskite precursor solution; mixing cesium iodide solution with the above solution, stirring and reacting for 24 hours, and depositing perovskite solution on the FTO/electron transport layer by two-step spin coating, wherein the two-step spin coating is respectively carried out for 10s at 1000rpm and 20s at 6000 rpm; 200. Mu.L of chlorobenzene was then dropped on the substrate, and the perovskite film was immediately annealed at 100℃for 1 hour.
(4) Preparation of hole transport layer: 72.3mg of 2,2', 7' -tetrakis [ N, N-bis (4-methoxyphenyl) amino ] -9,9' -spirobifluorene (Spiro-OMeTAD), 29. Mu.L of tributyl phosphate (TBP) and 17.5. Mu.L of lithium bistrifluoromethane-sulfonimide (Li-TFSI) are dissolved in 1mL of chlorobenzene, the crushed MOF-ET23 is dispersed in the chlorobenzene, after uniform stirring, a proper amount of solution is taken out and spin-coated on the perovskite film prepared in the step (3) at 4000 rpm;
and simultaneously preparing a hole transport layer without adding the MOF-ET23 material for comparison.
(5) Preparation of a metal electrode: and depositing an Au electrode with a thickness of 80nm by adopting a vacuum thermal evaporation mode.
The perovskite solar cell is prepared through the steps, and the structural composition schematic diagram of the prepared perovskite solar cell is shown in fig. 8.
The performance of perovskite solar cells is characterized below.
(1) Electrochemical impedance characteristic test:
through CHI660D electrochemical workstation, under the illumination of simulated sunlight AM1.5G, an external bias voltage of 0V is applied, the test frequency is 0.01-100KHz, and ZSimpWin software is utilized, so that the impedance characteristic spectrogram of the battery can be obtained and compared with a perovskite solar cell without MOF-ET23 material.
The electrochemical impedance characteristic curve obtained by testing is shown in fig. 9, and it is obvious from the graph that compared with a perovskite solar cell without the MOF-ET23 material, the radius of curvature of a high-frequency region transmission impedance arc corresponding to the cell with the MOF-ET23 material is obviously reduced, which means that the charge transmission impedance is obviously reduced, and the charge transport can be accelerated. This demonstrates that the introduction of MOF-ET23 can reduce thin film grain boundary defects, accelerate charge transport inside the battery, inhibit charge recombination, and thereby achieve enhancement of the photoelectric performance of the battery.
(2) J-V (Current Density-Voltage) curve test:
by digital Source Table (Keithley 2400) at AM1.5G,100mWcm -2 Under the condition of simulating sunlight light source, carrying out current-voltage test on the perovskite solar cell to obtain short-circuit current (J) sc ) Open circuit voltage (V) oc ) Fill Factor (FF) and Photoelectric Conversion Efficiency (PCE), and compared to perovskite solar cells without MOF-ET23 material added.
The J-V curve of the perovskite solar cell is shown in FIG. 10, and the photoelectric conversion efficiency of the perovskite solar cell added with the MOF-ET23 material is PCE= 24.68%, and the open circuit voltage V is obtained oc =1.19v, short-circuit current J sc =24.74mAcm -2 The filling factor ff=0.84, which indicates that the perovskite solar cell has higher photoelectric conversion efficiency, and the perovskite solar cell without MOF-ET23 material has the photoelectric conversion efficiency of only 19.44%, which proves that the perovskite solar cell provided by the application has more excellent performance.
It will be apparent that the above embodiments are merely examples for clarity of illustration and that other forms of modification or variation may be made in light of the above description. Thus, obvious variations or modifications may be made by those skilled in the art to which the invention pertains.
Claims (4)
1. A ligand for preparing a metal organic framework material, characterized by the following structural formula:
2. a metal organic framework material prepared by using the ligand for preparing the metal organic framework material according to claim 1, wherein the metal organic framework material has a composition formula of Tb 3 (L) 2 Wherein L is C 14 H 12 N 6 O 2 The structure of L is identical to the ligand structure described in claim 1.
3. Use of the metal-organic framework material of claim 2 in perovskite solar cells.
4. A perovskite solar cell comprising a conductive glass substrate, an electron transport layer, a perovskite absorber layer, a hole transport layer, and a metal electrode, wherein the hole transport layer comprises the metal organic framework material of claim 2.
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