CN109053468B - Fullerene ammonium tripropionate derivative, preparation method and application thereof - Google Patents

Fullerene ammonium tripropionate derivative, preparation method and application thereof Download PDF

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CN109053468B
CN109053468B CN201810718069.6A CN201810718069A CN109053468B CN 109053468 B CN109053468 B CN 109053468B CN 201810718069 A CN201810718069 A CN 201810718069A CN 109053468 B CN109053468 B CN 109053468B
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fullerene
ammonium
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冯莱
王琛
周东营
刘萍
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    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
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Abstract

The invention relates to a fullerene ammonium tripropionate derivative, a preparation method and application thereof, wherein the fullerene ammonium tripropionate derivative has a chemical structural general formula as follows:
Figure DDA0001717993230000011
the method has stronger polarity and excellent alcohol solubility, and can prepare a cathode interface layer by one step by a solution method; the cell efficiency and the service life of the perovskite solar cell with the cathode interface layer are obviously improved.

Description

Fullerene ammonium tripropionate derivative, preparation method and application thereof
Technical Field
The invention belongs to the field of photovoltaic materials and devices, and particularly relates to a fullerene ammonium tripropionate derivative, a preparation method and application thereof.
Background
Perovskite solar cells (pescs) are a new and rapidly developing photovoltaic technology, and have attracted extensive attention due to their characteristics of high efficiency, low cost, and easy processing. Among them, the planar perovskite solar cell is considered to have almost all the advantages of an organic polymer solar cell (OPV), and the structure is similar, so that the mature preparation process of OPV can be largely adopted. Most importantly, planar perovskite solar cells can achieve higher efficiencies than OPVs. In short years, the photoelectric conversion efficiency of the planar perovskite solar cell exceeds 21%, so that the planar perovskite solar cell becomes a research hotspot in the field of solar energy.
For PeSC, the work function of the cathode needs to be matched with the LUMO energy level of the electron transport layer and the perovskite layer, and the energy level matching is beneficial to forming (quasi-) ohmic contact between the perovskite layer/the electron transport layer/the cathode, so that a smaller carrier transport barrier and a larger open-circuit voltage (V) of the battery are obtainedOC). In planar p-i-n type perovskite solar cells, metals with low work functions, such as Al (-4.1 eV), can be used as cathodes, resulting in efficient electron transport. However, these low work function metals are susceptible to oxidation in an air environment, resulting in a short device lifetime. And the use of high work function metals such as Ag (4.7 eV) as the cathode can improve the stability of the device. However, high work function metals and typical electron transport layer materials PC61The LUMO levels (-3.9 eV) of the BM and perovskite are not matched, and have large energy level differences, which are not favorable for collection and transmission of photo-generated electrons.
To address this problem, previous studies have suggested that a Cathode Interface Layer (CIL) may be interposed between the electron transport layer and the metal cathode to improve the energy alignment between the electron transport layer/cathode to enhance electron transport. Typical cathode interface layer materials include metal fluorides (e.g., LiF) and some small n-type organic molecules (e.g., BCP, C)60BPhen, PCBC). In addition, previous researches found that some organic small molecule materials with strong polarity (such as PFN, PN4N, C)60Bis, PDINO and the like) can also be used as a cathode interface layer material, so that the work function of a metal electrode can be reduced, the interface energy level of an electron transport layer/cathode can be matched, the efficiency of the device can be improved, and the preparation method can be adopted, so that the preparation cost of the device can be reduced.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a fullerene ammonium tripropionate derivative.
In order to achieve the purpose, the invention adopts the technical scheme that: a fullerene ammonium tripropionate derivative has a chemical structural general formula as follows:
Figure BDA0001717993210000021
still another object of the present invention is to provide a method for producing the above fullerene tripropylammonium phosphate derivative, which comprises the steps of:
(a) will be provided with
Figure BDA0001717993210000022
Adding the mixture into tetramethyl ammonium hydroxide aqueous solution for stirring reaction, and then dropwise adding the mixture into acetone to generate yellow precipitate;
(b) dissolving the yellow precipitate in water, dropwise adding the yellow precipitate into acetone to generate yellow precipitate, and centrifuging;
(c) repeating the step (b) for a plurality of times, and drying the obtained yellow precipitate in vacuum.
It is still another object of the present invention to provide an application of the above fullerene tripropionic acid ammonium derivative, wherein the fullerene tripropionic acid ammonium derivative is used for forming a cathode interface layer.
Preferably, the fullerene tripropyl diacid ammonium derivative is dissolved in ethanol or isopropanol to form a solution, and then the solution is coated on the surface of an electron transport layer in a spinning mode to form a cathode interface layer.
Optimally, the cathode interface layer film is assembled into a planar p-i-n type perovskite solar cell, and the planar p-i-n type perovskite solar cell comprises a transparent ITO conductive substrate, a hole transport layer, a perovskite photoactive layer, an electron transport layer, a cathode interface layer and an Ag electrode which are sequentially stacked.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages: the fullerene ammonium tripropionate derivative has a specific chemical structure general formula, has strong polarity and excellent alcohol solubility, and can be used for preparing a cathode interface layer by one step by a solution method; the cell efficiency and the service life of the perovskite solar cell with the cathode interface layer are obviously improved.
Drawings
FIG. 1 shows fullerene derivatives e, e, e-C of the present invention60[C(CO2N(CH3)4)2]3Schematic diagram of structure and synthetic route of (1);
FIG. 2 shows fullerene derivatives e, e, e-C of the present invention60[C(CO2N(CH3)4)2]3Is/are as follows1H NMR spectrum;
FIG. 3 shows fullerene derivatives e, e, e-C of the present invention60[C(CO2N(CH3)4)2]3Absorption spectrum in aqueous solution;
FIG. 4 is a schematic diagram of the structure of a p-i-n type perovskite solar cell in the present invention;
FIG. 5 is a current density-voltage (J-V) plot of perovskite solar cells made in various embodiments of the present invention;
FIG. 6 is a graph showing the change of photoelectric conversion efficiency with time in comparative examples and examples of the present invention.
Detailed Description
The fullerene ammonium tripropionate derivative has a chemical structural general formula as follows:
Figure BDA0001717993210000031
(abbreviation e, e, e-C60[C(CO2N(CH3)4)2]3). The fullerene ammonium tripropionate derivative with the structure has stronger polarity and excellent alcohol solubility, and a cathode interface layer can be prepared by one step by adopting a solution method; the cell efficiency and the service life of the perovskite solar cell with the cathode interface layer are obviously improved.
The preparation method of the fullerene ammonium tripropionate derivative comprises the following steps: (a) will be provided with
Figure BDA0001717993210000032
(abbreviated as e, e, e-C)60[C(COOH)2]3) Adding the mixture into tetramethyl ammonium hydroxide aqueous solution for stirring reaction, and then dropwise adding the mixture into acetone to generate yellow precipitate; (b) dissolving the yellow precipitate in water, dropwise adding the yellow precipitate into acetone to generate yellow precipitate, and centrifuging; (c) repeating step (b) for a plurality of times, and vacuum drying the obtained yellow precipitateDrying.
The application of the fullerene tripropionic acid ammonium derivative is to use the fullerene tripropionic acid ammonium derivative for preparing a cathode interface layer. Preferably, the fullerene tripropyl diacid ammonium derivative is dissolved in ethanol or isopropanol to form a solution, and then the solution is coated on the surface of an electron transport layer in a spinning mode to form a cathode interface layer; more specifically: assembling the cathode interface layer film into a planar p-i-n type perovskite solar cell, wherein the planar p-i-n type perovskite solar cell comprises a transparent ITO conductive substrate, a hole transport layer, a perovskite photoactive layer, an electron transport layer, a cathode interface layer and an Ag electrode which are sequentially stacked; the transparent ITO conductive substrate is generally ITO conductive glass; the hole transport layer is typically PEDOT: PSS; the perovskite photoactive layer is typically CH3NH3PbCl3- xIxThe thickness of the perovskite thin film is generally 300-350 nm; the electron transport layer is typically a PC61BM, typically about 20 to 100nm thick; the metal electrode is usually Ag and has a thickness of 50-200 nm.
The preferred embodiments of the present invention will be described in detail below with reference to the accompanying drawings:
example 1
This embodiment provides a method for preparing an ammonium fullerene tripropylate derivative, as shown in fig. 1, which includes the following steps:
(a) 6.8mg of e, e, e-C60[C(COOH)2]3Dissolving in 200 μ L aqueous solution (2 wt%) of tetramethylammonium hydroxide, heating and stirring at 60 deg.C for reaction for 12 hr; dropwise adding the reaction mixture into 3mL of acetone solution to generate yellow precipitate, and centrifugally separating to remove supernatant;
(b) dissolving the precipitate in 3mL of water, adding the solution dropwise into acetone to generate yellow precipitate, and centrifuging;
(c) repeating the step (b) for 2-3 times, and performing vacuum drying to obtain 8.9mg of e, e, e-C60[C(CO2N(CH3)4)2]3The yield was about 90%.1H-NMR(ppm,D2O) 3.04(s, 72H); as shown in FIG. 2, the single peak at 3.04ppm corresponds to the hydrogen of the methyl group on the Tetramethylammonium (TMA) group, indicating that the fullerene (e, e)The e) -tripropyl diacid derivative has been completely converted into the fullerene tetramethyl ammonium tripropionate derivative. The ultraviolet visible absorption spectrum of the product is shown in FIG. 3, and characteristic absorption peaks at 280nm, e, e-C can be seen60[C(COOH)2]3The characteristic absorption peaks of (A) are consistent, which shows that the structural characteristics of the fullerene are not changed.
Example 2
This example provides a method for preparing an ammonium fullerene tripropylate derivative, which is substantially the same as in example 1, except that: heating and stirring at 60 ℃ to react for 3 h; vacuum drying to obtain 8.7mg of e, e, e-C60[C(CO2N(CH3)4)2]3The yield was about 90%.
Example 3
This example provides a method for preparing an ammonium fullerene tripropylate derivative, which is substantially the same as in example 1, except that: heating and stirring at 30 ℃ for reaction for 3 h; vacuum drying to obtain 7.3mg of e, e, e-C60[C(CO2N(CH3)4)2]3The yield was about 70%.
Example 4
This example provides an application of a fullerene ammonium tripropionate derivative to the fabrication of a planar p-i-n perovskite solar cell having a cathode transport layer (the structure of the planar p-i-n perovskite solar cell is shown in fig. 4, and includes a transparent ITO conductive substrate 6, a hole transport layer 5, a perovskite photoactive layer 4, an electron transport layer 3, a cathode interface layer 2, and an Ag electrode 1, which are sequentially stacked), and the specific preparation method thereof includes the following steps:
(1) cleaning of ITO conductive glass (i.e., transparent ITO conductive substrate 6): ultrasonic cleaning with deionized water, acetone, ethanol and isopropanol for 15min, and oven drying at 100 deg.C;
(2) preparation of hole transport layer 5 (PEDOT: PSS film): PEDOT was coated on ITO conductive glass using spin coating: PSS film (working parameter: 2000 r/min, time 40s), and annealing at 150 deg.C for 15min in air atmosphere;
(3) preparation of perovskite photoactive layer: a. CH (CH)3NH3PbIxCl3-xPreparing a precursor solution: will CH3NH3I，PbCl2And PbI2Mixing the raw materials in a ratio of 5.75: 1.6: 1 in N, N-Dimethylformamide (DMF), and heating and stirring at 60 ℃ for 12 hours under a nitrogen atmosphere; b.CH3NH3PbIxCl3-xPreparing a film: in the PEDOT: coating CH on PSS film by using spin coating method3NH3PbIxCl3-xThe film (working parameters: 4000 rpm, 40s) is placed in the atmosphere of nitrogen and annealed at 80 ℃ for 2 hours;
(4) electron transport layer PC61Preparation of BM films: preparation of PC61BM in chlorobenzene at a concentration of 20 mg/mL; in CH3NH3PbIxCl3-xCoating of PC by spin coating on films61BM film (working parameters: 2000 r/min, time 40s) with thickness of about 40 nm;
(5) preparing a cathode interface layer: preparation of e, e, e-C60[C(CO2N(CH3)4)2]3The ethanol solution of (1), at a concentration of about 0.5 mg/mL; at PC61The fullerene derivative film is coated on the BM film by using a spin coating method (working parameters: 2000 rpm, 40 s);
(6) preparing a metal electrode: and (3) evaporating a metal Ag electrode with the thickness of about 100nm on the surface of the electron transport layer/cathode interface layer to obtain the planar p-i-n type perovskite solar cell.
Under standard test conditions (atmospheric mass AM 1.5, light intensity 100 mW/cm)2) The J-V curve test was performed on the battery prepared in this example, and the results are shown in fig. 5; the cell performance is shown in Table 1, with an open circuit voltage of 0.927V and a short circuit current of 20.75mA/cm2The fill factor was 68.72%, and the photoelectric conversion efficiency was 13.22%.
Example 5
This example provides the use of a fullerene ammonium tripropionate derivative, which differs from the basic one of example 4 by: in step (5), e, e, e-C is prepared60[C(CO2N(CH3)4)2]3The ethanol solution of (1.0 mg/mL); at PC61The fullerene derivative film is coated on the BM film by using a spin coating method (working parameters: 2000 rpm, 40 s); under standard test conditions (atmospheric mass AM 1.5, light intensity 100 mW/cm)2) The J-V curve test was performed on the battery prepared in this example, and the results are shown in fig. 5. The cell performance is shown in Table 1, with an open circuit voltage of 0.929V and a short circuit current of 20.86mA/cm2The fill factor was 69.13%, and the photoelectric conversion efficiency was 13.40%.
Example 6
This example provides the use of a fullerene ammonium tripropionate derivative, which differs from the basic one of example 4 by: in step (5), e, e, e-C is prepared60[C(CO2N(CH3)4)2]3The ethanol solution of (1), concentration is about 1.5 mg/mL; at PC61The fullerene derivative film is coated on the BM film by using a spin coating method (working parameters: 2000 rpm, 40 s); under standard test conditions (atmospheric mass AM 1.5, light intensity 100 mW/cm)2) The J-V curve test was performed on the battery prepared in this example, and the results are shown in fig. 5. The cell performance is shown in Table 1, with an open circuit voltage of 0.939V and a short circuit current of 19.41mA/cm2The fill factor was 70.87%, and the photoelectric conversion efficiency was 12.92%.
Example 7
This example provides the use of a fullerene ammonium tripropionate derivative, which differs from the basic one of example 4 by: in step (5), e, e, e-C is prepared60[C(CO2N(CH3)4)2]3The ethanol solution of (1), at a concentration of about 2.0 mg/mL; at PC61The fullerene derivative film is coated on the BM film by using a spin coating method (working parameters: 2000 rpm, 40 s); under standard test conditions (atmospheric mass AM 1.5, light intensity 100 mW/cm)2) The J-V curve test was performed on the battery prepared in this example, and the results are shown in fig. 5. The cell performance is shown in Table 1, with an open circuit voltage of 0.916V and a short circuit current of 19.81mA/cm2The filling factor is 69.65%, and the photoelectric conversion efficiency is 12.64%.
Comparative example 1
This example provides the use of a fullerene tripropionic acid ammonium derivative, which differs from the basic one in example 4 by: step (5) is not performed, and the electronic transmission layer PC is directly formed61And evaporating a metal electrode on the BM film. Under standard test conditions (atmospheric mass AM 1.5, light intensity 100 mW/cm)2) The J-V curve test was performed on the battery prepared in this example, and the results are shown in fig. 5. The cell performance is shown in Table 1, with an open circuit voltage of 0.927V and a short circuit current of 18.18mA/cm2The fill factor was 62.56%, and the photoelectric conversion efficiency was 10.55%.
Comparative example 2
This example provides the use of a fullerene ammonium tripropionate derivative, which differs from the basic one of example 4 by: in the step (5), preparing an ethanol solution of 4, 7-diphenyl-1, 10-phenanthroline (BPhen), wherein the concentration is about 0.5 mg/mL; at PC61Coating a BPhen film on the BM film by using a spin-coating method (working parameters: 2000 rpm, 40 s); under standard test conditions (atmospheric mass AM 1.5, light intensity 100 mW/cm)2) The J-V curve test was performed on the battery prepared in this example, and the results are shown in fig. 5. The cell performance is shown in Table 1, with an open circuit voltage of 0.928V and a short circuit current of 18.70mA/cm2The fill factor was 72.26%, and the photoelectric conversion efficiency was 12.54%.
Comparative example 3
This example provides the use of a fullerene ammonium tripropionate derivative, which differs from the basic one of example 4 by: in step (5), e, e, e-C is prepared60[C(COOH)2]3The ethanol solution of (1), at a concentration of about 0.5 mg/mL; at PC61The fullerene derivative film is coated on the BM film by using a spin coating method (working parameters: 2000 rpm, 40 s); under standard test conditions (atmospheric mass AM 1.5, light intensity 100 mW/cm)2) The J-V curve test was performed on the battery prepared in this example, and the results are shown in fig. 5. The cell performance is shown in Table 1, with an open circuit voltage of 0.927V and a short circuit current of 17.35mA/cm2The fill factor was 57.86%, and the photoelectric conversion efficiency was 9.31%.
Comparing examples 4-7 with comparative examples 1-3, it can be seen that there are e, e, e-C60[C(CO2N(CH3)4)2]3The performance of the perovskite solar cell with the cathode interface layer is remarkably higher than that of a device without the cathode interface layer (as shown in figure 5, specific parameters are shown in table 1); wherein, e, e, e-C60[C(CO2N(CH3)4)2]3When the concentration of the solution is 0.5-1 mg/mL, the efficiency of the device reaches 13.22-13.40%, and compared with the device without a cathode interface layer (comparative example 1), the efficiency is improved by 30%. The devices of examples 4-7 were more efficient than devices with a typical cathode interface layer material, Bphen, as the cathode transport layer (comparative example 2), indicating that e, e, e-C60[C(CO2N(CH3)4)2]3Is a cathode interface layer material which is more excellent than Bphen. In addition, if the fullerene derivative is e, e, e-C60[C(COOH)2]3As a cathode interface layer (comparative example 3), the device efficiency was lower, even slightly lower, than the device without a cathode interface layer (comparative example 1). This illustrates e, e, e-C60[C(COOH)2]3Is not a good cathode interface layer material, but the conversion of the material into the tetramethylammonium compound obtains higher molecular polarity, so that dipole moment favorable for electron transmission can be formed on an electron transmission layer/cathode interface, an electron injection barrier is reduced, the electron transmission collection is enhanced, and the efficiency of the device is improved.
The stability test of the planar p-i-n type perovskite solar cells prepared in the example 4 and the comparative example 1 is specifically as follows: the perovskite solar cells prepared in example 4 and comparative example 1 were stored in a glove box (nitrogen atmosphere, room temperature), and the stability thereof was tested, respectively, as shown in fig. 6; it can be seen that the PCE of the perovskite solar cell prepared in example 4 still retained 80% of the initial value after 12 days, and the PCE of the perovskite solar cell prepared in comparative example 1 decayed 31% after 12 days, only 69% of the initial value, indicating the use of e, e, e-C60[C(CO2N(CH3)4)2]3As the cathode interface layer, the stability of the device is improved. It is apparent that the improvement in device stability can be attributed to the e, e, e-C based60[C(CO2N(CH3)4)2]3The cathode interfacial layer of (a). Because the interface layer contains a large amount of tetramethylammonium cation, or I which can inhibit diffusion from the perovskite layer to the cathode interface-And the ions corrode the metal Ag electrode, so that the stability of the device is improved.
TABLE 1 Performance parameter Table for planar p-i-n perovskite solar cells in examples 4-7 and comparative examples 1-3
Figure BDA0001717993210000071
The above embodiments are merely illustrative of the technical concept and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the content of the present invention and implement the invention, and not to limit the scope of the invention, and all equivalent changes or modifications made according to the spirit of the present invention should be covered by the scope of the present invention.

Claims (5)

1. A fullerene ammonium tripropionate derivative is characterized by having a chemical structural general formula as follows:
Figure FDA0002678050470000011
2. a method of producing an ammonium fullerene tripropylate derivative according to claim 1, characterized in that it comprises the steps of:
(a) will be provided with
Figure FDA0002678050470000012
Adding the mixture into tetramethyl ammonium hydroxide aqueous solution for stirring reaction, and then dropwise adding the mixture into acetone to generate yellow precipitate;
(b) dissolving the yellow precipitate in water, dropwise adding the yellow precipitate into acetone to generate yellow precipitate, and centrifuging;
(c) repeating the step (b) for a plurality of times, and drying the obtained yellow precipitate in vacuum.
3. The use of an ammonium fullerene tripropylate derivative according to claim 1, characterized in that: the fullerene tripropyl ammonium diacid derivative is used for preparing a cathode interface layer.
4. The use of an ammonium fullerene tripropylate derivative according to claim 3, characterized in that: and dissolving the fullerene ammonium tripropionate derivative in ethanol or isopropanol to form a solution, and then spin-coating the solution on the surface of the electron transport layer to form a cathode interface layer.
5. The use of an ammonium fullerene tripropylate derivative according to claim 3, characterized in that: and assembling the cathode interface layer into a planar p-i-n type perovskite solar cell, wherein the planar p-i-n type perovskite solar cell comprises a transparent ITO conductive substrate, a hole transport layer, a perovskite photoactive layer, an electron transport layer, a cathode interface layer and an Ag electrode which are sequentially stacked.
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