CN110707221A - Application of amino acid ionic liquid in preparation of perovskite layer in perovskite photoelectric device - Google Patents

Application of amino acid ionic liquid in preparation of perovskite layer in perovskite photoelectric device Download PDF

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CN110707221A
CN110707221A CN201910910618.4A CN201910910618A CN110707221A CN 110707221 A CN110707221 A CN 110707221A CN 201910910618 A CN201910910618 A CN 201910910618A CN 110707221 A CN110707221 A CN 110707221A
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ionic liquid
perovskite
amino acid
acid
solar cell
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CN110707221B (en
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陶国华
张磊
张国浩
何玲
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Peking University Shenzhen Graduate School
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    • HELECTRICITY
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    • H10K30/00Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/10Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising heterojunctions between organic semiconductors and inorganic semiconductors
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    • H10K71/00Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10Deposition of organic active material
    • H10K71/12Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/15Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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    • H10K71/00Manufacture or treatment specially adapted for the organic devices covered by this subclass
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Abstract

The invention discloses an application of amino acid ionic liquid in preparation of a perovskite layer in a perovskite photoelectric device, wherein the amino acid ionic liquid is amino acid salt ionic liquid or amino acid ester ionic liquid, and the general formula of the amino acid salt ionic liquid is [ A ]]n+[X]nThe general formula of the amino acid ester ionic liquid is [ HA ]1COOR]+XWherein A is an amino acid, A1Is the part of A molecule except carboxyl, n ranges from 1 to 4, and XRepresents an anion, R is an alkyl group having 1 to 3 carbon atoms. Researches find that the surface appearance of the perovskite layer can be regulated by using the amino acid ionic liquid, so that the performance of the formed perovskite photoelectric device is improved, and the method has great application value in the field of perovskite photoelectric devices.

Description

Application of amino acid ionic liquid in preparation of perovskite layer in perovskite photoelectric device
Technical Field
The invention relates to an amino acid ionic liquid, in particular to an application of the amino acid ionic liquid in preparation of a perovskite layer in a perovskite photoelectric device.
Background
Solar technology is an effective means for solving the world energy crisis, and a high-efficiency and low-cost solar cell is the basis of a photovoltaic system. As a third-generation solar cell, since 2009, perovskite solar cells have attracted extensive attention by researchers due to their advantages of high absorption coefficient, high carrier mobility, long carrier transport distance, low cost, solution processibility, and the like. The development of the perovskite solar cell is short, and the photoelectric conversion efficiency of the perovskite solar cell is broken through from 3.8% to 22.7%. How to improve the photoelectric conversion efficiency and stability of the perovskite solar cell is a main problem of current research.
The growth of perovskite crystal is a complex phase transition process, and the final crystal morphology and structure are different due to different factors such as solution, temperature, solvent, additives and the like in a reaction system. In a planar heterojunction perovskite solar cell, the solar cell structure is influenced by an interface effect and surface tension during perovskite crystallization, so that the perovskite thin film has too high crystallization speed and poor film forming property, more pores in a perovskite layer and larger surface roughness. The hole transport layer or the electron transport layer deposited subsequently can be directly contacted with the compact layer through the holes, so that the leakage current of the battery is increased. The perovskite crystal with lattice distortion also has great influence on parameters such as the band gap of the perovskite thin film, the carrier mobility, the interface carrier injection and the like. These factors can cause the performance of the planar heterojunction perovskite solar cell device to be greatly reduced, and the development of the perovskite solar cell technology is greatly limited. Therefore, preparing a perovskite crystal thin film with high quality and low defect state, and further improving the photoelectric conversion efficiency, stability and repeatability of the battery is one of the key problems to be solved in the field. At present, researchers adopt a plurality of means to regulate and control the quality of a perovskite layer, for example, in 2015, Huangjinsong and other people add a strong coordination solvent DMSO into a commonly used DMF solvent, and realize the control of crystal growth and crystal morphology by inhibiting rapid crystallization of lead iodide. In 2012, Snaith et al introduced a chlorine-containing compound into the precursor solution to change the degree of crystallization of lead iodide methylamine, reduce the defects of the perovskite thin film, and increase the carrier diffusion length.
Ionic liquids are liquids that are composed entirely of ions, typically consisting of a specific volume of a relatively large, structurally asymmetric organic cation and a small volume of anion. The ionic liquid has a plurality of types, theoretically, any given organic cation and anion can be combined into the ionic liquid, and different types of ionic liquids can be obtained by changing the types of the organic cation and the anion. The amino acid ionic liquid belongs to one kind of ionic liquid, and natural amino acid and its derivatives can be used as both anion and cation of ionic liquid, such as glycine nitrate (GlyNO)3) And 1-ethyl-3-methyl-imidazole glycinate (emigliy), and the like. Similar to conventional ionic liquid, the amino acid ionic liquid has high thermal stability, and in addition, the amino acid ionic liquid also has unique properties such as stronger hydrogen bond network structure, capability of dissolving DNA and the like. At present, the performance research based on the amino acid ionic liquid mainly focuses on the chiral catalysis aspect, and no research on the aspect of regulating and controlling the shape of the perovskite layer is found so far.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art. Therefore, the invention provides the application of the amino acid ionic liquid in the preparation of a perovskite layer in a perovskite photoelectric device, and researches show that the amino acid ionic liquid has the function of regulating the morphology of the perovskite layer and is beneficial to improving the performance of the perovskite photoelectric device.
The technical scheme adopted by the invention is as follows:
the invention provides an application of an amino acid ionic liquid in preparation of a perovskite layer in a perovskite photoelectric device, wherein the amino acid ionic liquid is an amino acid salt ionic liquid or an amino acid ester ionic liquid, and the general formula of the amino acid salt ionic liquid is [ A ]]n+[X-]nThe general formula of the amino acid ester ionic liquid is [ HA ]1COOR]+X-Wherein A is an amino acid, A1Is the part of A molecule except carboxyl, n ranges from 1 to 4, and X-Represents an anion, R is an alkyl group having 1 to 3 carbon atoms.
According to some embodiments of the invention, the amino acid is selected from the group consisting of glycine, D-methionine, L-methionine, DL-methionine, D-alanine, L-alanine, DL-alanine, D-valine, L-valine, DL-valine, D-leucine, L-leucine, DL-leucine, D-isoleucine, L-isoleucine, DL-isoleucine, D-phenylalanine, L-phenylalanine, DL-phenylalanine, D-cysteine, L-cysteine, DL-cysteine, D-cystine, L-cystine, DL-cystine, D-threonine, L-threonine, DL-threonine, D-glutamic acid, L-methionine, L-valine, L-leucine, L-isoleucine, l-glutamic acid, DL-glutamic acid, D-glutamine, L-glutamine, DL-glutamine, D-aspartic acid, L-aspartic acid, DL-aspartic acid, D-asparagine, L-asparagine, DL-asparagine, D-methionine, L-methionine, DL-methionine, D-serine, L-serine, DL-serine, D-proline, L-proline, DL-proline, D-tyrosine, L-tyrosine, DL-tyrosine, D-tryptophan, L-tryptophan, DL-tryptophan, D-lysine, L-lysine, DL-lysine, D-arginine, L-arginine, DL-arginine, L-glutamine, L-methionine, L-proline, D-tyrosine, L-arginine, D-histidine, L-histidine, DL-histidine, D-ornithine, L-ornithine, DL-ornithine, beta-alanine, 2-aminobutyric acid, 3-aminobutyric acid, 4-aminobutyric acid, 2-aminoisobutyric acid, 3-aminoisobutyric acid, 2-aminovaleric acid, 2-aminohexanoic acid, 6-aminohexanoic acid, o-aminophenylpropionic acid, p-aminophenylpropionic acid, m-aminophenylpropionic acid.
According to some embodiments of the invention, X-Selected from Cl-(chloride ion), Br-(Bromide ion), I-(iodide ion), NO3 -(nitrate radical), ClO4 -(perchlorate) CF3CO2 -(trifluoroacetate), CH3CO2 -(acetate), NTf2 -(bis (trifluoromethanesulfonylimide) radical), PF6 -(Hexafluorophosphate), BF4 -(tetrafluoroborate), CF3SO3 -(trifluoromethanesulfonate).
According to some embodiments of the invention, the perovskite optoelectronic device is a perovskite solar cell.
In a second aspect of the invention, there is provided an anti-solvent for use in the preparation of a perovskite layer, comprising an amino acid ionic liquid as described in the above application.
According to some embodiments of the invention, further comprising chlorinated benzenes.
According to some embodiments of the invention, the mass fraction of the amino acid ionic liquid in the antisolvent is 0.01 to 2 wt%.
In a third aspect of the present invention, there is provided a method for producing a perovskite solar cell, comprising the step of producing a perovskite layer by an anti-solvent method, wherein the anti-solvent used is the anti-solvent for producing a perovskite layer described above.
According to some embodiments of the invention, the step of preparing the perovskite layer by the anti-solvent method comprises: coating the perovskite precursor solution on a substrate, dropwise adding the anti-solvent in the coating process, and then annealing at 80-100 ℃ to obtain the perovskite layer.
In a fourth aspect of the invention, a perovskite solar cell is provided, which is manufactured according to the above perovskite solar cell manufacturing method.
The embodiment of the invention has the beneficial effects that:
according to the research of the embodiment of the invention, the amino acid ionic liquid is utilized to effectively reduce the crystallization rate of perovskite, and form a perovskite layer with higher crystallinity and lower roughness, so that the defect of the perovskite layer is reduced, the band gap of the perovskite active layer is changed, and the leakage current phenomenon of a perovskite solar photoelectric device is effectively reduced.
Drawings
FIG. 1 is a surface topography of the perovskite layer produced in example 1 and the perovskite layer in comparative example 1;
fig. 2 is a performance curve of the solar cell manufactured in example 1 and the solar cell manufactured in comparative example 1.
Detailed Description
The concept and technical effects of the present invention will be clearly and completely described below in conjunction with the embodiments to fully understand the objects, features and effects of the present invention. It is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments, and those skilled in the art can obtain other embodiments without inventive effort based on the embodiments of the present invention, and all embodiments are within the protection scope of the present invention.
Example 1
In the embodiment, the D-phenylalanine methyl ester hexafluorophosphate ionic liquid is selected as an object, the influence of the D-phenylalanine methyl ester hexafluorophosphate ionic liquid on the morphology of a perovskite layer and the performance of a solar cell is researched, and the specific experimental process is as follows:
preparing D-phenylalanine methyl ester hexafluorophosphate ionic liquid:
taking 0.10mol of D-phenylalanine methyl ester hydrochloride and 0.12mol of potassium hexafluorophosphate, stirring for 50h in 20mL of acetonitrile, filtering to obtain a filtrate, and removing the solvent from the filtrate through rotary evaporation to obtain the D-phenylalanine methyl ester hexafluorophosphate ionic liquid.
Preparing a solar cell:
(1) weighing iodomethylamine and lead iodide in a molar ratio of 1:1 in a nitrogen-protected constant-temperature glove box, dissolving in N, N-Dimethylformamide (DMF) solution, fully dissolving, and heating at a constant temperature of 60 ℃ for 24 h. Cooling for 0.5h to room temperature to prepare the perovskite precursor mixed solution.
(2) Preparing an anti-solvent: and (2) dissolving the prepared D-phenylalanine methyl ester hexafluorophosphate ionic liquid in chlorobenzene, and mixing to form an antisolvent, wherein the mass fraction of the D-phenylalanine methyl ester hexafluorophosphate ionic liquid is 0.1 wt%.
(3) And ultrasonically cleaning the etched ITO conductive glass respectively by using an optical cleaning agent, distilled water, acetone and isopropanol for 20min, blow-drying by using nitrogen, then cleaning by using a PLASMA surface cleaning instrument for 15min by using ozone, blowing the nitrogen clean, and putting the ITO conductive glass into a dust-free culture dish for later use.
(4) Preparing a hole transport layer: and spin-coating a 2mg/mL toluene solution of PTAA on the cleaned ITO conductive glass, controlling the rotating speed to be 6000rpm and the spin-coating time to be 35s, and then annealing at 110 ℃ for 20min to form a hole transport layer.
(5) Preparing a perovskite layer: transferring the ITO conductive glass spin-coated with the PTAA into a nitrogen-protected constant-temperature glove box, dropwise adding a perovskite precursor mixed solution onto a hole transport layer, spin-coating at the rotating speed of 5000rpm for 8s, dropwise adding an anti-solvent, dropwise adding the anti-solvent for 3s, closing a spin-coating instrument, and annealing on a hot bench at the temperature of 80 ℃ for 10min to obtain a perovskite layer.
(6) Preparing an electron transport layer: 20mg/mL of PC61And spin-coating a chlorobenzene solution of BM on the perovskite layer at the rotating speed of 2000rpm for 30s to obtain the electron transport layer.
(7) Preparing an electron transport layer modification layer: and spin-coating 12mg/mL ZnO trifluoroethanol solution at the rotation speed of 4000rpm to form a film on the electron transport layer, wherein the spin-coating time is 60s to form the electron transport layer modification layer.
(8) Evaporating a counter electrode: and evaporating a 150 nm-thick metal aluminum electrode by a vacuum coating machine.
Comparative example 1: comparative example 1 provides a solar cell, which has the same structure and fabrication process as those of the solar cell of example 1, except that the D-phenylalanine methyl ester hexafluorophosphate ionic liquid was not added to the anti-solvent of step (5) of fabricating the perovskite layer.
SEM characterization of the surface morphology of the perovskite layer produced in this example and the perovskite layer in comparative example 1 was performed, and the results are shown in fig. 1, in which (a) in fig. 1 shows an SEM image of the perovskite layer in the perovskite solar cell to which the D-phenylalanine methyl ester hexafluorophosphate ionic liquid was added, and (b) in fig. 1 shows an SEM image of the perovskite layer in the perovskite solar cell to which the ionic liquid was not added. As can be seen from FIG. 1, the perovskite layer prepared by using the anti-solvent containing the D-phenylalanine methyl ester hexafluorophosphate ionic liquid has larger grain size and smaller edge density, and the result shows that the D-phenylalanine methyl ester hexafluorophosphate ionic liquid has the function of regulating the morphology of the perovskite layer.
The solar cell manufactured in the present example and the solar cell manufactured in comparative example 1 were tested for their performance, and the results are shown in fig. 2The results are shown at 100mW/cm2The test is carried out under illumination (the effective area is 0.06 cm)2) In this embodiment, the short-circuit current (Jsc) of the solar cell is 22.81mA/cm2The open circuit voltage (Voc) was 1.07V, the Fill Factor (FF) was 0.76, the Photoelectric Conversion Efficiency (PCE) was 18.5%, and the short circuit current (Jsc) of the solar cell in comparative example 1 was 22.51mA/cm2The open circuit voltage (Voc) is 1.02V, the Fill Factor (FF) is 0.73, and the Photoelectric Conversion Efficiency (PCE) is 16.7%. The result shows that the performance of the solar cell can be improved by using the D-phenylalanine methyl ester hexafluorophosphate ionic liquid.
Example 2
The embodiment provides a solar cell, wherein an amino acid ionic liquid in an anti-solvent used in a process of preparing a perovskite layer is an L-alanine hexafluorophosphate ionic liquid, and the specific experimental process is as follows:
preparing an L-alanine hexafluorophosphate ionic liquid:
dissolving 0.10mol of L-alanine and 0.10mol of hexafluorophosphoric acid in 10mL of water, heating to 60 ℃, then drying in vacuum for 12h, and cooling to obtain the L-alanine hexafluorophosphate ionic liquid.
Preparing a solar cell:
(1) weighing iodomethylamine and lead iodide in a molar ratio of 1:1 in a nitrogen-protected constant-temperature glove box, dissolving in N, N-Dimethylformamide (DMF) solution, fully dissolving, and heating at a constant temperature of 60 ℃ for 24 h. Cooling for 0.5h to room temperature to prepare the perovskite precursor mixed solution.
(2) Preparing an anti-solvent: and dissolving the prepared L-alanine hexafluorophosphate ionic liquid in chlorobenzene, and mixing to form an antisolvent, wherein the mass fraction of the L-alanine hexafluorophosphate ionic liquid is 0.2 wt%.
(3) And ultrasonically cleaning the etched ITO conductive glass respectively by using an optical cleaning agent, distilled water, acetone and isopropanol for 20min, blow-drying by using nitrogen, then cleaning by using a PLASMA surface cleaning instrument for 15min by using ozone, blowing the nitrogen clean, and putting the ITO conductive glass into a dust-free culture dish for later use.
(4) Preparing a hole transport layer: and spin-coating a 2mg/mL toluene solution of PTAA on the cleaned ITO conductive glass, controlling the rotating speed to be 6000rpm and the spin-coating time to be 35s, and then annealing at 110 ℃ for 20min to form a hole transport layer.
(5) Preparing a perovskite layer: transferring the ITO conductive glass spin-coated with the PTAA into a nitrogen-protected constant-temperature glove box, dropwise adding a perovskite precursor mixed solution onto a hole transport layer, spin-coating at the rotating speed of 5000rpm for 7s, dropwise adding an anti-solvent, dropwise adding the anti-solvent for 3s, closing a spin-coating instrument, and annealing on a hot bench at the temperature of 85 ℃ for 10min to obtain a perovskite layer.
(6) Preparing an electron transport layer: 20mg/mL of PC61And spin-coating a chlorobenzene solution of BM on the perovskite layer at the rotating speed of 2000rpm for 30s to obtain the electron transport layer.
(7) Preparing an electron transport layer modification layer: and spin-coating 12mg/mL ZnO trifluoroethanol solution at the rotation speed of 4000rpm to form a film on the electron transport layer, wherein the spin-coating time is 60s to form the electron transport layer modification layer.
(8) Evaporating a counter electrode: and evaporating a 150 nm-thick metal aluminum electrode by a vacuum coating machine.
The performance of the solar cell fabricated in this example was tested and the results were shown to be 100mW/cm2The test is carried out under illumination (the effective area is 0.06 cm)2) In this embodiment, the short-circuit current (Jsc) of the solar cell is 22.13mA/cm2The open-circuit voltage (Voc) is 1.08V, the Fill Factor (FF) is 0.74, and the Photoelectric Conversion Efficiency (PCE) is 17.7%, and the results show that the solar cell treated with the D-phenylalanine methyl ester hexafluorophosphate ionic liquid has excellent photoelectric conversion performance.
Example 3
This example provides a solar cell, where the amino acid ionic liquid in the anti-solvent used in the process of preparing a perovskite layer is selected from a D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid and a DL-valine bis (trifluoromethanesulfonyl) imide salt ionic liquid, and the specific experimental process is as follows:
preparing D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid:
dissolving 0.10mol of D-leucine hydrochloride and 0.12mol of lithium bis (trifluoromethanesulfonyl) imide in 1mL of water, reacting for 60h, taking the lower clear liquid, drying for 12h in vacuum, and cooling to obtain the D-leucine bis (trifluoromethanesulfonyl) imide ionic liquid.
Preparing DL-valine bis (trifluoromethanesulfonyl) imide salt ionic liquid:
dissolving 0.10mol of DL-valine hydrochloride and 0.12mol of lithium bis (trifluoromethanesulfonyl) imide in 1mL of water, reacting for 60h, taking the lower clear liquid, drying for 12h in vacuum, and cooling to obtain the DL-valine bis (trifluoromethanesulfonyl) imide ionic liquid.
Preparing a solar cell:
(1) weighing iodomethylamine and lead iodide in a molar ratio of 1:1 in a nitrogen-protected constant-temperature glove box, dissolving in N, N-Dimethylformamide (DMF) solution, fully dissolving, and heating at a constant temperature of 60 ℃ for 24 h. Cooling for 0.5h to room temperature to prepare the perovskite precursor mixed solution.
(2) Preparing an anti-solvent: and (2) dissolving the prepared D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid and DL-valine bis (trifluoromethanesulfonyl) imide salt ionic liquid in chlorobenzene, and mixing to form an antisolvent, wherein the mass fraction of the D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid is 0.1 wt%, and the mass fraction of the DL-valine bis (trifluoromethanesulfonyl) imide salt ionic liquid is 0.15 wt%.
(3) And ultrasonically cleaning the etched ITO conductive glass respectively by using an optical cleaning agent, distilled water, acetone and isopropanol for 20min, blow-drying by using nitrogen, then cleaning by using a PLASMA surface cleaning instrument for 15min by using ozone, blowing the nitrogen clean, and putting the ITO conductive glass into a dust-free culture dish for later use.
(4) Preparing a hole transport layer: and spin-coating a 2mg/mL toluene solution of PTAA on the cleaned ITO conductive glass, controlling the rotating speed to be 6000rpm and the spin-coating time to be 35s, and then annealing at 110 ℃ for 20min to form a hole transport layer.
(5) Preparing a perovskite layer: transferring the ITO conductive glass spin-coated with the PTAA into a nitrogen-protected constant-temperature glove box, dropwise adding a perovskite precursor mixed solution onto a hole transport layer, spin-coating at the rotating speed of 5000rpm for 7s, dropwise adding an anti-solvent, dropwise adding the anti-solvent for 3s, closing a spin-coating instrument, and annealing on a hot bench at the temperature of 90 ℃ for 8min to obtain a perovskite layer.
(6) Preparing an electron transport layer: 20mg/mL of PC61And spin-coating a chlorobenzene solution of BM on the perovskite layer at the rotating speed of 2000rpm for 30s to obtain the electron transport layer.
(7) Preparing an electron transport layer modification layer: and spin-coating 12mg/mL ZnO trifluoroethanol solution at the rotation speed of 4000rpm to form a film on the electron transport layer, wherein the spin-coating time is 60s to form the electron transport layer modification layer.
(8) Evaporating a counter electrode: and evaporating a 150 nm-thick metal aluminum electrode by a vacuum coating machine.
The performance of the solar cell fabricated in this example was tested and the results were shown to be 100mW/cm2The test is carried out under illumination (the effective area is 0.06 cm)2) In this embodiment, the short-circuit current (Jsc) of the solar cell is 23.17mA/cm2The open-circuit voltage (Voc) was 1.08V, the Fill Factor (FF) was 0.75, and the Photoelectric Conversion Efficiency (PCE) was 18.8%, and the results showed that the solar cell obtained by treatment with the D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid and the DL-valine bis (trifluoromethanesulfonyl) imide salt ionic liquid had excellent photoelectric conversion performance.
Example 4
The embodiment provides a solar cell, wherein an amino acid ionic liquid in an anti-solvent used in a process of preparing a perovskite layer is an L-serine methyl ester hexafluorophosphate ionic liquid and an L-serine ethyl ester hexafluorophosphate ionic liquid, and the specific experimental process comprises the following steps:
preparing an L-serine methyl ester hexafluorophosphate ionic liquid:
taking 0.10mol of L-serine methyl ester hydrochloride and 0.12mol of potassium hexafluorophosphate, stirring in 1mL of water for 60h, taking the supernatant, drying in vacuum for 12h, and cooling to obtain the L-serine methyl ester hexafluorophosphate ionic liquid.
Preparing an L-serine ethyl ester hexafluorophosphate ionic liquid:
and (3) stirring 0.10mol of L-serine ethyl ester hydrochloride and 0.12mol of potassium hexafluorophosphate in 1mL of water for 60h, taking the supernatant, drying in vacuum for 12h, and cooling to obtain the L-serine ethyl ester hexafluorophosphate ionic liquid.
Preparing a solar cell:
(1) weighing iodomethylamine and lead iodide in a molar ratio of 1:1 in a nitrogen-protected constant-temperature glove box, dissolving in N, N-Dimethylformamide (DMF) solution, fully dissolving, and heating at a constant temperature of 60 ℃ for 24 h. Cooling for 0.5h to room temperature to prepare the perovskite precursor mixed solution.
(2) Preparing an anti-solvent: and dissolving the prepared L-serine methyl ester hexafluorophosphate ionic liquid and L-serine ethyl ester hexafluorophosphate ionic liquid in chlorobenzene, and mixing to form an antisolvent, wherein the mass fraction of the L-serine methyl ester hexafluorophosphate ionic liquid is 0.1 wt%, and the mass fraction of the L-serine ethyl ester hexafluorophosphate ionic liquid is 0.12 wt%.
(3) And ultrasonically cleaning the etched ITO conductive glass respectively by using an optical cleaning agent, distilled water, acetone and isopropanol for 20min, blow-drying by using nitrogen, then cleaning by using a PLASMA surface cleaning instrument for 15min by using ozone, blowing the nitrogen clean, and putting the ITO conductive glass into a dust-free culture dish for later use.
(4) Preparing a hole transport layer: and spin-coating a 2mg/mL toluene solution of PTAA on the cleaned ITO conductive glass, controlling the rotating speed to be 6000rpm and the spin-coating time to be 35s, and then annealing at 110 ℃ for 20min to form a hole transport layer.
(5) Preparing a perovskite layer: transferring the ITO conductive glass spin-coated with the PTAA into a nitrogen-protected constant-temperature glove box, dropwise adding a perovskite precursor mixed solution onto a hole transport layer, spin-coating at the rotating speed of 5000rpm for 8s, dropwise adding an anti-solvent, dropwise adding the anti-solvent for 3s, closing a spin-coating instrument, and annealing on a hot bench at the temperature of 85 ℃ for 10min to obtain a perovskite layer.
(6) Preparing an electron transport layer: 20mg/mL of PC61And spin-coating a chlorobenzene solution of BM on the perovskite layer at the rotating speed of 2000rpm for 30s to obtain the electron transport layer.
(7) Preparing an electron transport layer modification layer: and spin-coating 12mg/mL ZnO trifluoroethanol solution at the rotation speed of 4000rpm to form a film on the electron transport layer, wherein the spin-coating time is 60s to form the electron transport layer modification layer.
(8) Evaporating a counter electrode: and evaporating a 150 nm-thick metal aluminum electrode by a vacuum coating machine.
The performance of the solar cell fabricated in this example was tested and the results were shown to be 100mW/cm2The test is carried out under illumination (the effective area is 0.06 cm)2) In this embodiment, the short-circuit current (Jsc) of the solar cell is 22.69mA/cm2The open-circuit voltage (Voc) was 1.06V, the Fill Factor (FF) was 0.76, and the Photoelectric Conversion Efficiency (PCE) was 18.3%, and the results showed that the solar cell treated with the L-serine methyl ester hexafluorophosphate ionic liquid and the L-serine ethyl ester hexafluorophosphate ionic liquid had excellent photoelectric conversion performance.
Example 5
The embodiment provides a solar cell, wherein an amino acid ionic liquid in an anti-solvent used in a process of preparing a perovskite layer is a D-methionine methyl ester hexafluorophosphate ionic liquid and a D-methionine methyl ester tetrafluoroborate ionic liquid, and the specific experimental process is as follows:
preparing D-methionine methyl ester hexafluorophosphate ionic liquid:
and (3) taking 0.10mol of D-methionine methyl ester hydrochloride and 0.12mol of potassium hexafluorophosphate, stirring in 1mL of water for 60h, taking the supernatant, drying in vacuum for 12h, and cooling to obtain the D-methionine methyl ester hexafluorophosphate ionic liquid.
Preparation of D-methionine methyl ester tetrafluoroborate ionic liquid:
and (3) stirring 0.10mol of D-methionine methyl ester hydrochloride and 0.12mol of sodium tetrafluoroborate in 1mL of water for 60h, taking the supernatant, drying for 12h in vacuum, and cooling to obtain the D-methionine methyl ester tetrafluoroborate ionic liquid.
Preparing a solar cell:
(1) weighing iodomethylamine and lead iodide in a molar ratio of 1:1 in a nitrogen-protected constant-temperature glove box, dissolving in N, N-Dimethylformamide (DMF) solution, fully dissolving, and heating at a constant temperature of 60 ℃ for 24 h. Cooling for 0.5h to room temperature to prepare the perovskite precursor mixed solution.
(2) Preparing an anti-solvent: dissolving the prepared D-methionine methyl ester hexafluorophosphate ionic liquid and D-methionine methyl ester tetrafluoroborate ionic liquid in chlorobenzene, and mixing to form an anti-solvent, wherein the mass fraction of the D-methionine methyl ester hexafluorophosphate ionic liquid is 0.2 wt%, and the mass fraction of the D-methionine methyl ester tetrafluoroborate ionic liquid is 0.3 wt%.
(3) And ultrasonically cleaning the etched ITO conductive glass respectively by using an optical cleaning agent, distilled water, acetone and isopropanol for 20min, blow-drying by using nitrogen, then cleaning by using a PLASMA surface cleaning instrument for 15min by using ozone, blowing the nitrogen clean, and putting the ITO conductive glass into a dust-free culture dish for later use.
(4) Preparing a hole transport layer: and spin-coating a 2mg/mL toluene solution of PTAA on the cleaned ITO conductive glass, controlling the rotating speed to be 6000rpm and the spin-coating time to be 35s, and then annealing at 110 ℃ for 20min to form a hole transport layer.
(5) Preparing a perovskite layer: transferring the ITO conductive glass spin-coated with the PTAA into a nitrogen-protected constant-temperature glove box, dropwise adding a perovskite precursor mixed solution onto a hole transport layer, spin-coating at the rotating speed of 5000rpm for 8s, dropwise adding an anti-solvent, dropwise adding the anti-solvent for 3s, closing a spin-coating instrument, and annealing on a hot bench at the temperature of 100 ℃ for 8min to obtain a perovskite layer.
(6) Preparing an electron transport layer: a20 mg/mL solution of PC61BM in chlorobenzene was spin-coated on the perovskite layer at 2000rpm for 30 seconds to obtain an electron transport layer.
(7) Preparing an electron transport layer modification layer: and spin-coating 12mg/mL ZnO trifluoroethanol solution at the rotation speed of 4000rpm to form a film on the electron transport layer, wherein the spin-coating time is 60s to form the electron transport layer modification layer.
(8) Evaporating a counter electrode: and evaporating a 150 nm-thick metal aluminum electrode by a vacuum coating machine.
The performance of the solar cell fabricated in this example was tested and the results were shown to be 100mW/cm2The test is carried out under illumination (the effective area is 0.06 cm)2) In this embodiment, the short-circuit current (Jsc) of the solar cell is 21.98mA/cm2Open circuit voltage (Voc) 1.09V, Fill Factor (FF) 0.75, Photoelectric Conversion Efficiency (PCE) 18.0%, and the results indicate that D-methionine methyl ester hexafluorophosphate ionic liquid and D-methionine are usedThe solar cell obtained by the treatment of the methyl tetrafluoroborate ionic liquid has excellent photoelectric conversion performance.
Example 6
The embodiment provides a solar cell, wherein an amino acid ionic liquid in an anti-solvent used in a process of preparing a perovskite layer is glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid, and the specific experimental process is as follows:
preparing glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid:
and (3) stirring 0.10mol of glycine methyl ester hydrochloride and 0.12mol of lithium bis (trifluoromethanesulfonyl) imide in 1mL of water for 60h, taking the supernatant, drying in vacuum for 12h, and cooling to obtain glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid.
Preparing a solar cell:
(1) weighing iodomethylamine and lead iodide in a molar ratio of 1:1 in a nitrogen-protected constant-temperature glove box, dissolving in N, N-Dimethylformamide (DMF) solution, fully dissolving, and heating at a constant temperature of 60 ℃ for 24 h. Cooling for 0.5h to room temperature to prepare the perovskite precursor mixed solution.
(2) Preparing an anti-solvent: dissolving the prepared glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid in chlorobenzene, and mixing to form an antisolvent, wherein the mass fraction of the glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid is 0.1 wt%.
(3) And ultrasonically cleaning the etched ITO conductive glass respectively by using an optical cleaning agent, distilled water, acetone and isopropanol for 20min, blow-drying by using nitrogen, then cleaning by using a PLASMA surface cleaning instrument for 15min by using ozone, blowing the nitrogen clean, and putting the ITO conductive glass into a dust-free culture dish for later use.
(4) Preparing a hole transport layer: and spin-coating a 2mg/mL toluene solution of PTAA on the cleaned ITO conductive glass, controlling the rotating speed to be 6000rpm and the spin-coating time to be 35s, and then annealing at 110 ℃ for 20min to form a hole transport layer.
(5) Preparing a perovskite layer: transferring the ITO conductive glass spin-coated with the PTAA into a nitrogen-protected constant-temperature glove box, dropwise adding a perovskite precursor mixed solution onto a hole transport layer, spin-coating at the rotating speed of 5000rpm for 8s, dropwise adding an anti-solvent, dropwise adding the anti-solvent for 3s, closing a spin-coating instrument, and annealing on a hot bench at the temperature of 80 ℃ for 10min to obtain a perovskite layer.
(6) Preparing an electron transport layer: 30mg/mL of PC61BM in chlorobenzene solution was spin-coated on the perovskite layer at 2500rpm for 30 seconds to obtain an electron transport layer.
(7) Preparing an electron transport layer modification layer: and spin-coating 12mg/mL ZnO trifluoroethanol solution at the rotation speed of 4000rpm to form a film on the electron transport layer, wherein the spin-coating time is 60s to form the electron transport layer modification layer.
(8) Evaporating a counter electrode: and evaporating a 200 nm-thick metal aluminum electrode by a vacuum coating machine.
The performance of the solar cell fabricated in this example was tested and the results were shown to be 100mW/cm2The test is carried out under illumination (the effective area is 0.06 cm)2) In this embodiment, the short-circuit current (Jsc) of the solar cell is 20.89mA/cm2The open-circuit voltage (Voc) is 1.06V, the Fill Factor (FF) is 0.63, and the Photoelectric Conversion Efficiency (PCE) is 14.0%, and the results show that the solar cell treated with the glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid has excellent photoelectric conversion performance.
Example 7
This example provides a solar cell, where an amino acid ionic liquid in an anti-solvent used in a process of preparing a perovskite layer is selected from a D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid and a D-valine bis (trifluoromethanesulfonyl) imide salt ionic liquid, and a specific experimental process is as follows:
preparing D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid:
and (3) stirring 0.10mol of D-leucine hydrochloride and 0.12mol of lithium bis (trifluoromethanesulfonyl) imide in 1mL of water for 60h, taking the supernatant, drying in vacuum for 12h, and cooling to obtain the D-leucine bis (trifluoromethanesulfonyl) imide ionic liquid.
Preparing D-valine bis (trifluoromethanesulfonyl) imide salt ionic liquid:
and (3) stirring 0.10mol of D-valine and 0.12mol of lithium bis (trifluoromethanesulfonyl) imide in 1mL of water for 60h, taking the supernatant, drying in vacuum for 12h, and cooling to obtain the D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid.
Preparing a solar cell:
(1) weighing iodomethylamine and lead iodide in a molar ratio of 1:1 in a nitrogen-protected constant-temperature glove box, dissolving in N, N-Dimethylformamide (DMF) solution, fully dissolving, and heating at a constant temperature of 60 ℃ for 24 h. Cooling for 0.5h to room temperature to prepare the perovskite precursor mixed solution.
(2) Preparing an anti-solvent: and (2) dissolving the prepared D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid and D-valine bis (trifluoromethanesulfonyl) imide salt ionic liquid in chlorobenzene, and mixing to form an antisolvent, wherein the mass fraction of the D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid is 0.1 wt%, and the mass fraction of the D-valine bis (trifluoromethanesulfonyl) imide salt ionic liquid is 0.15 wt%.
(3) And ultrasonically cleaning the etched ITO conductive glass respectively by using an optical cleaning agent, distilled water, acetone and isopropanol for 20min, blow-drying by using nitrogen, then cleaning by using a PLASMA surface cleaning instrument for 15min by using ozone, blowing the nitrogen clean, and putting the ITO conductive glass into a dust-free culture dish for later use.
(4) Preparing a hole transport layer: and spin-coating a 2mg/mL toluene solution of PTAA on the cleaned ITO conductive glass, controlling the rotating speed to be 6000rpm and the spin-coating time to be 35s, and then annealing at 110 ℃ for 20min to form a hole transport layer.
(5) Preparing a perovskite layer: transferring the ITO conductive glass spin-coated with the PTAA into a nitrogen-protected constant-temperature glove box, dropwise adding a perovskite precursor mixed solution onto a hole transport layer, spin-coating at the rotating speed of 5000rpm for 8s, dropwise adding an anti-solvent, dropwise adding the anti-solvent for 3s, closing a spin-coating instrument, and annealing on a hot bench at the temperature of 80 ℃ for 10min to obtain a perovskite layer.
(6) Preparing an electron transport layer: 30mg/mL of PC61BM in chlorobenzene solution was spin-coated on the perovskite layer at 2500rpm for 30 seconds to obtain an electron transport layer.
(7) Preparing an electron transport layer modification layer: and spin-coating 12mg/mL ZnO trifluoroethanol solution at the rotation speed of 4000rpm to form a film on the electron transport layer, wherein the spin-coating time is 60s to form the electron transport layer modification layer.
(8) Evaporating a counter electrode: and evaporating a 200 nm-thick metal aluminum electrode by a vacuum coating machine.
The performance of the solar cell fabricated in this example was tested and the results were shown to be 100mW/cm2The test is carried out under illumination (the effective area is 0.06 cm)2) In this embodiment, the short-circuit current (Jsc) of the solar cell is 21.04mA/cm2The open-circuit voltage (Voc) is 1.07V, the Fill Factor (FF) is 0.58, and the Photoelectric Conversion Efficiency (PCE) is 13.1%, and the results show that the solar cell treated with the D-leucine bis (trifluoromethanesulfonyl) imide salt ionic liquid and the D-valine bis (trifluoromethanesulfonyl) imide salt ionic liquid has excellent photoelectric conversion performance.
Example 8
The embodiment provides a solar cell, wherein an amino acid ionic liquid in an anti-solvent used in a process of preparing a perovskite layer is glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid, and the specific experimental process is as follows:
preparing glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid:
and (3) stirring 0.10mol of glycine methyl ester hydrochloride and 0.12mol of lithium bis (trifluoromethanesulfonyl) imide in 1mL of water for 60h, taking the supernatant, drying in vacuum for 12h, and cooling to obtain glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid.
Preparing a solar cell:
(1) weighing iodomethylamine and lead iodide in a molar ratio of 1:1 in a nitrogen-protected constant-temperature glove box, dissolving in N, N-Dimethylformamide (DMF) solution, fully dissolving, and heating at a constant temperature of 60 ℃ for 24 h. Cooling for 0.5h to room temperature to prepare the perovskite precursor mixed solution.
(2) Preparing an anti-solvent: dissolving the prepared glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid in chlorobenzene, and mixing to form an antisolvent, wherein the mass fraction of the glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid is 0.5 wt%.
(3) And ultrasonically cleaning the etched ITO conductive glass respectively by using an optical cleaning agent, distilled water, acetone and isopropanol for 20min, blow-drying by using nitrogen, then cleaning by using a PLASMA surface cleaning instrument for 15min by using ozone, blowing the nitrogen clean, and putting the ITO conductive glass into a dust-free culture dish for later use.
(4) Preparing a hole transport layer: and spin-coating a 2mg/mL toluene solution of PTAA on the cleaned ITO conductive glass, controlling the rotating speed to be 6000rpm and the spin-coating time to be 35s, and then annealing at 110 ℃ for 20min to form a hole transport layer.
(5) Preparing a perovskite layer: transferring the ITO conductive glass spin-coated with the PTAA into a nitrogen-protected constant-temperature glove box, dropwise adding a perovskite precursor mixed solution onto a hole transport layer, spin-coating at the rotating speed of 5000rpm for 8s, dropwise adding an anti-solvent, dropwise adding the anti-solvent for 3s, closing a spin-coating instrument, and annealing on a hot bench at the temperature of 80 ℃ for 10min to obtain a perovskite layer.
(6) Preparing an electron transport layer: 30mg/mL of PC61BM in chlorobenzene solution was spin-coated on the perovskite layer at 2500rpm for 30 seconds to obtain an electron transport layer.
(7) Preparing an electron transport layer modification layer: and spin-coating 12mg/mL ZnO trifluoroethanol solution at the rotation speed of 4000rpm to form a film on the electron transport layer, wherein the spin-coating time is 60s to form the electron transport layer modification layer.
(8) Evaporating a counter electrode: and evaporating a 200 nm-thick metal aluminum electrode by a vacuum coating machine.
The performance of the solar cell prepared in this example was tested, and the results show that the solar cell treated with the glycine methyl ester bis (trifluoromethanesulfonyl) imide ionic liquid has excellent photoelectric conversion performance.
Example 9
The embodiment provides a solar cell, wherein an amino acid ionic liquid in an anti-solvent used in a process of preparing a perovskite layer is a p-aminophenylpropionic acid nitrate ionic liquid and a 2-aminopentanoic acid acetate ionic liquid, and the specific experimental process is as follows:
preparing p-aminophenylpropionic acid nitrate ionic liquid:
dissolving 0.10mol of p-aminophenylpropionic acid and 0.10mol of 65% nitric acid in 10mL of water, reacting for 24h, distilling under reduced pressure at 60 ℃ to remove water, and drying in vacuum for 24h to obtain the p-aminophenylpropionic acid nitrate ionic liquid.
Preparing 2-aminopentanoic acid acetate ionic liquid:
dissolving 0.10mol of 2-aminopentanoic acid and 0.10mol of trifluoroacetic acid in 10mL of water, reacting for 24h, distilling under reduced pressure at 60 ℃ to remove water, and drying in vacuum for 24h to obtain the 2-aminopentanoic acid acetate ionic liquid.
Preparing a solar cell:
(1) weighing iodomethylamine and lead iodide in a molar ratio of 1:1 in a nitrogen-protected constant-temperature glove box, dissolving in N, N-Dimethylformamide (DMF) solution, fully dissolving, and heating at a constant temperature of 60 ℃ for 24 h. Cooling for 0.5h to room temperature to prepare the perovskite precursor mixed solution.
(2) And ultrasonically cleaning the etched ITO conductive glass respectively by using an optical cleaning agent, distilled water, acetone and isopropanol for 20min, blow-drying by using nitrogen, then cleaning by using a PLASMA surface cleaning instrument for 15min by using ozone, blowing the nitrogen clean, and putting the ITO conductive glass into a dust-free culture dish for later use.
(3) Preparing a hole transport layer: and spin-coating a 2mg/mL toluene solution of PTAA on the cleaned ITO conductive glass, controlling the rotating speed to be 6000rpm and the spin-coating time to be 35s, and then annealing at 110 ℃ for 20min to form a hole transport layer.
(4) Preparing a perovskite layer: transferring the ITO conductive glass spin-coated with the PTAA into a nitrogen-protected constant-temperature glove box, spin-coating the perovskite precursor mixed solution on a hole transport layer at the rotating speed of 5000rpm, and annealing on a hot bench at the temperature of 80 ℃ for 10min to obtain a perovskite layer.
(5) Mixing p-aminophenylpropionic acid nitrate ionic liquid and 2-aminopentanoic acid acetate ionic liquid to form mixed ionic liquid, soaking a perovskite layer in the mixed ionic liquid for 1h, taking out, flushing by using chlorobenzene, and drying by using high-purity nitrogen.
(6) Preparing an electron transport layer: 30mg/mL of PC61BM in chlorobenzene solution was spin-coated on the perovskite layer at 2500rpm for 30 seconds to obtain an electron transport layer.
(7) Preparing an electron transport layer modification layer: and spin-coating 12mg/mL ZnO trifluoroethanol solution at the rotation speed of 4000rpm to form a film on the electron transport layer, wherein the spin-coating time is 60s to form the electron transport layer modification layer.
(8) Evaporating a counter electrode: and evaporating a 200 nm-thick metal aluminum electrode by a vacuum coating machine.
The performance of the solar cell prepared in the embodiment is tested, and the result shows that the solar cell obtained by soaking the p-aminophenylpropionic acid nitrate ionic liquid and the 2-aminopentanoic acid acetate ionic liquid has excellent photoelectric conversion performance.

Claims (10)

1. The application of amino acid ionic liquid in preparation of perovskite layer in perovskite photoelectric device is characterized in that the amino acid ionic liquid is amino acid salt ionic liquid or amino acid ester ionic liquid, and the general formula of the amino acid salt ionic liquid is [ A ]]n+[X-]nThe general formula of the amino acid ester ionic liquid is [ HA ]1COOR]+X-Wherein A is an amino acid, A1Is the part of A molecule except carboxyl, n ranges from 1 to 4, and X-Represents an anion, R is an alkyl group having 1 to 3 carbon atoms.
2. The use according to claim 1, wherein the amino acid is selected from the group consisting of glycine, D-methionine, L-methionine, DL-methionine, D-alanine, L-alanine, DL-alanine, D-valine, L-valine, DL-valine, D-leucine, L-leucine, D-isoleucine, L-isoleucine, DL-isoleucine, D-phenylalanine, L-phenylalanine, DL-phenylalanine, D-cysteine, L-cysteine, DL-cysteine, D-cystine, L-cystine, DL-cystine, D-threonine, L-threonine, DL-threonine, L-methionine, L-leucine, L-isoleucine, L-leucine, L, D-glutamic acid, L-glutamic acid, DL-glutamic acid, D-glutamine, L-glutamine, DL-glutamine, D-aspartic acid, L-aspartic acid, DL-aspartic acid, D-asparagine, L-asparagine, DL-asparagine, D-methionine, L-methionine, DL-methionine, D-serine, L-serine, DL-proline, L-proline, DL-proline, D-tyrosine, L-tyrosine, DL-tyrosine, D-tryptophan, L-tryptophan, DL-tryptophan, D-lysine, L-lysine, DL-lysine, D-arginine, L-glutamine, L-methionine, L-, DL-arginine, D-histidine, L-histidine, DL-histidine, D-ornithine, L-ornithine, DL-ornithine, beta-alanine, 2-aminobutyric acid, 3-aminobutyric acid, 4-aminobutyric acid, 2-aminoisobutyric acid, 3-aminoisobutyric acid, 2-aminopentanoic acid, 2-aminocaproic acid, 6-aminocaproic acid, o-aminophenylpropionic acid, p-aminophenylpropionic acid, m-aminophenylpropionic acid.
3. Use according to claim 1, characterized in that X-Selected from Cl-、Br-、I-、NO3 -、ClO4 -、CF3CO2 -、CH3CO2 -、NTf2 -、PF6 -、BF4 -、CF3SO3 -Any one of the above.
4. Use according to any one of claims 1 to 3, wherein the perovskite optoelectronic device is a perovskite solar cell.
5. An antisolvent for use in the preparation of a perovskite layer, comprising an amino acid ionic liquid as described in any one of claims 1 to 3.
6. The antisolvent for producing a perovskite layer according to claim 5, further comprising chlorobenzene.
7. The antisolvent for producing a perovskite layer according to claim 6, wherein the mass fraction of the amino acid ionic liquid in the antisolvent is 0.01 to 2 wt%.
8. A method of producing a perovskite solar cell, comprising the step of producing a perovskite layer by an anti-solvent method, wherein the anti-solvent used is the anti-solvent for producing a perovskite layer according to any one of claims 5 to 7.
9. The method for producing a perovskite solar cell according to claim 8, wherein the step of producing the perovskite layer by an anti-solvent method comprises: coating the perovskite precursor solution on a substrate, dropwise adding the anti-solvent in the coating process, and then annealing at 80-100 ℃ to obtain the perovskite layer.
10. A perovskite solar cell, characterized by being produced according to the method for producing a perovskite solar cell of claim 8 or 9.
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