CN111454211A - Hydroxyl functionalized imidazolium salt, preparation method thereof and application thereof in perovskite solar cell - Google Patents

Hydroxyl functionalized imidazolium salt, preparation method thereof and application thereof in perovskite solar cell Download PDF

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CN111454211A
CN111454211A CN202010153204.4A CN202010153204A CN111454211A CN 111454211 A CN111454211 A CN 111454211A CN 202010153204 A CN202010153204 A CN 202010153204A CN 111454211 A CN111454211 A CN 111454211A
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hydroxyl
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王忠胜
程浩亮
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Abstract

The invention belongs to the technical field of solar cells, and particularly relates to hydroxyl functionalized imidazolium salt, a preparation method thereof and application thereof in perovskite solar cells. The hydroxyl functionalized imidazolium salt takes the terminal as hydroxyl, imidazole as a core, an imidazole N atom replaces an aromatic ring, and an anion is halogen or halogen-like; hydroxyl functionalized imidazolium salt is self-assembled on the surface of the FTO conductive substrate, and the FTO modified by the ionic conductor is used as the conductive substrate in the perovskite solar cell, so that excellent photovoltaic performance can be obtained. The FTO has the following advantages: in the hydroxyl functionalized imidazolium salt, the terminal hydroxyl can be anchored on the FTO surface in a chemical bond bonding mode, so that the ion conductor is firmly assembled on the FTO surface; the work function of the FTO can be adjusted, and the open-circuit photovoltage can be adjusted; the charge extraction capability and the electron lifetime can be improved. The hydroxyl functionalized imidazolium salt has the advantages of simple structure, convenient preparation and high stability, and is a potential interface modification material.

Description

Hydroxyl functionalized imidazolium salt, preparation method thereof and application thereof in perovskite solar cell
Technical Field
The invention belongs to the technical field of solar cells, and particularly relates to a hydroxyl functionalized imidazolium salt, a preparation method thereof and application thereof in a perovskite solar cell.
Background
As a new type of photovoltaic device, Perovskite solar cells (Perovskite solar cells) have attracted extensive attention in both academic and industrial fields. The perovskite light absorption layer has the advantages of high molar extinction coefficient, wide light absorption range, long carrier diffusion length and the like. In the last decade, the energy conversion efficiency has increased rapidly from the first 3.8% to 24.2%. Perovskite solar cells are of two types, the forward and reverse structure. In the forward structure, the inorganic oxide TiO is generally adopted2As an electron transport layer, but because of the mesoporous TiO2Need 450oC high temperature annealing to improve its crystallinity limits its application to flexible substrates and increases energy dissipation and complexity of device fabrication. In order to simplify the structure of the battery and reduce the cost of the battery, a device structure without an electron transport layer is gradually reported, but the device without the electron transport layer has serious electron back transfer and recombination, and in addition, the work function of the conductive glass (FTO) is not matched with the conduction band energy level of the perovskite, so that the photoelectric performance of the perovskite solar battery device without the electron transport layer is seriously influenced.
Aiming at the problems of the perovskite solar cell device without the electron transport layer, the hydroxyl functionalized imidazolium salt is self-assembled on the surface of the FTO conductive substrate, the FTO modified by the ionic conductor is applied to the perovskite solar cell as the conductive substrate, and the electron transport material is not needed, so that excellent photovoltaic performance can be obtained. The FTO modified based on the ion conductor has the following advantages: (1) in the hydroxyl functionalized imidazolium salt, the terminal hydroxyl can be anchored on the FTO surface in a chemical bond bonding mode, so that the ion conductor is firmly assembled on the FTO surface; (2) the work function of the FTO can be adjusted, so that the open-circuit photovoltage is adjusted; (3) the charge extraction capability and the electron lifetime can be improved. The hydroxyl functionalized imidazolium salt has the advantages of simple structure, easy preparation and high stability, and is a potential interface modification material.
Disclosure of Invention
The invention aims to provide a hydroxyl functionalized imidazolium salt and a preparation method thereof, and the hydroxyl functionalized imidazolium salt is applied to a perovskite solar cell.
The hydroxyl functionalized imidazolium salt provided by the invention takes a terminal as a hydroxyl group, imidazole as a core, an aromatic ring is substituted on an imidazole N atom, and an anion is halogen or halogen-like, and the specific structural formula is as follows:
Figure DEST_PATH_IMAGE002
Figure DEST_PATH_IMAGE004
wherein: r is a compound of the structure shown by R1, R2, R3 or R4; x is Cl, Br, I, SCN, BF4、PF6Or TFSI; n =2~ 8.
In the present invention, typical imidazolium salt ionic conductors are as follows:
r = R3, X = I, n =2, imidazole salt as IC-1;
r = R2, X = I, n =2, imidazole salt as IC-2;
R = R1，X = BF4n =4, imidazole salt as IC-3;
R = R4，X = PF6n =3, imidazole salt IC-4;
r = R2, X = TFSI, n =5, imidazole salt as IC-5;
r = R3, X = SCN, n =6, imidazole salt as IC-6;
r = R3, X = Cl, n = 7, imidazole salt as IC-7;
r = R2, X = Br, n =8, imidazole salt as IC-8:
r = R1, X = Br, n =8, imidazole salt as IC-9;
when R = R4, X = I, and n =4, the imidazole salt was designated IC-10.
The specific structural formulas are respectively as follows:
Figure DEST_PATH_IMAGE006
Figure DEST_PATH_IMAGE008
Figure DEST_PATH_IMAGE010
Figure DEST_PATH_IMAGE012
Figure DEST_PATH_IMAGE014
Figure DEST_PATH_IMAGE016
Figure DEST_PATH_IMAGE018
Figure DEST_PATH_IMAGE020
Figure DEST_PATH_IMAGE022
Figure DEST_PATH_IMAGE024
。
the preparation method of the hydroxyl-containing functionalized imidazolium salt provided by the invention comprises the following synthetic route:
scheme 1:
Figure DEST_PATH_IMAGE026
scheme 2:
Figure DEST_PATH_IMAGE028
scheme 3:
Figure DEST_PATH_IMAGE029
。
the specific steps of scheme 1 are:
taking n-propanol as a solvent, and mixing a compound (a) and a compound (b): halogen-substituted alcohols, in a molar ratio of 1: (0.8-1.2), and reacting at 60-80 ℃ for 24-48 h to obtain a final product, which is marked as c; wherein, in the compound (a), R is R1, R2, R3 or R4; in compound (b), X = Cl, Br or I; n = 2-8;
(II) further, the specific steps of the synthetic route 2 are as follows:
using dichloromethane as solvent, mixing compound (c) and compound (d): NaX2According to the molar ratio of 1: (1-2) mixing, and reacting for 20-48 hours through ion exchange to obtain a final product, which is marked as e; in the compound (d), X is BF4、PF6Or SCN;
(III) further, the specific steps of the synthetic route 3 are as follows:
and (3) mixing the compound (c) and a compound f: L iTFSI according to a molar ratio of 1 (1-2) by using water as a solvent, and reacting for 20-48 hours through ion exchange to obtain a final product, which is recorded as g.
The hydroxyl functionalized imidazolium salt can be applied to perovskite solar cells and can greatly improve the energy conversion efficiency of the solar cells. The specific method comprises the following steps: hydroxyl functionalized imidazolium salt is used as an interface modification layer, then self-assembled on the surface of an FTO conductive substrate by a soaking method, and the FTO modified by an ionic conductor is applied to a perovskite solar cell as the conductive substrate without an electronic transmission material, so that excellent photovoltaic performance can be obtained.
For example, imidazole salt organic molecules IC-1 and IC-2 are applied to perovskite solar cells. The specific method comprises the following steps: and dissolving the hydroxyl functionalized imidazole salt in a trifluoroethanol solution, and fully dissolving to obtain a transparent and clear solution. And then soaking the FTO conductive glass subjected to ozone treatment in the solution for 8-24 h, taking out, washing molecules physically adsorbed on the surface of the FTO by using trifluoroethanol, and drying by using a nitrogen gun. Then spin coating perovskite, the perovskite used is CH3NH3PbI3After the perovskite thin film is sintered, a hole transport layer Spiro-OMeTAD is coated in a spinning mode, and then a layer of gold electrode is evaporated. The work functions of the molecules IC-1 and IC-2 are-4.44 and-4.40 eV, respectively, which is advantageous for obtaining a higher open circuit voltage. By using the IC-1 modified device, the open-circuit voltage of the battery reaches 1.077V, and the energy conversion efficiency reaches 15.99%. In the IC-2 modified device, the open-circuit voltage of the battery reaches 1.082V, and the energy conversion efficiency reaches 17.31%.
Imidazole salts based on hydroxyl functionalization have the following advantages:
(1) in the hydroxyl functionalized imidazole salt molecules, hydroxyl can be anchored on the surface of FTO in a chemical bond bonding mode, and the imidazole salt can be deposited in a soaking mode, so that the application of a large-area battery is facilitated;
(2) the work function of FTO can be realized, and the open-circuit photovoltage is improved;
(3) the electron lifetime and the charge extraction efficiency can be improved. In the simulated sunlight (100 mW cm)-2) Under irradiation, the energy conversion efficiency of the perovskite solar cell device based on the original FTO is 9.01%, wherein the open circuit photovoltage is 0.977V; after the FTO is modified by the imidazolium salt, the energy conversion efficiency of the solar cell is 15.99% and 17.31% respectively, and the open circuit photovoltage is 1.077V and 1.082V respectively. The energy conversion efficiency and the open circuit photovoltage are respectively and obviously improved.
The hydroxyl-containing functionalized imidazolium salt has the advantages of simple structure, easy preparation and high stability, and is a potential interface modification material applicable to perovskite solar cells.
Drawings
FIG. 1 is a J-V curve of a perovskite solar cell.
Detailed Description
The invention is further described by the following examples, but is not limited to the following examples.
Example 1: preparation of imidazole salt (denoted as IC-1) with R = R3, X = I, and n =2
The method specifically comprises the following steps: mixing a compound a (R = R3) and a compound b (X = I, n =2) in a molar ratio of 1:1.5 by using n-propanol as a solvent, adding the mixture to react at 80 ℃ for 24 hours, pouring the mixed solution after the reaction into anhydrous ether, generating a precipitate, and performing suction filtration and washing to obtain a white solid product with the yield of 86%.
1H NMR (400 MHz, DMSO-d 6 ) 9.72 (t, J = 3.2 Hz, 1 H), 8.29 (d, J = 8.0Hz, 1 H), 8.24 (t, J = 1.8 Hz, 1 H),8.19~8.22 (m, 1 H), 8.16 (t, J = 1.6 Hz,1 H), 7.87~7.89 (m, 1 H), 7.70~7.79 (m, 3 H), 7.62~7.66 (m, 1 H), 4.42 (t, J= 5.0 Hz, 2 H), 3.91 (t, J = 5.0 Hz, 2 H).13C NMR (100 MHz, DMSO-d 6 ) 138.6,134.2, 131.6, 131.5, 129.1, 129.0, 128.2, 128.0, 126.0, 125.4, 125.0, 123.8,121.8, 59.7, 52.8. ESI-HRMS (m/z): Calcd. for C15H15N2O+: 239.1178. Found:239.1179。
Example 2: preparation of imidazole salt (denoted as IC-2) with R = R2, X = I, and n =2
The method specifically comprises the following steps: mixing a compound a (R = R2) and a compound b (X1 = I, n =2) in a molar ratio of 1:1.8 by using n-propanol as a solvent, adding the mixture to react at 75 ℃ for 48 hours, pouring the mixed solution after the reaction into anhydrous ether, generating a precipitate, and performing suction filtration and washing to obtain a white solid with the yield of 88%.
1H NMR (400 MHz, DMSO-d 6 ) 9.87 (t, J = 3.2 Hz, 1 H), 8.38 (t, J = 1.8Hz, 1 H), 8.03 (t, J = 1.6 Hz, 1 H),7.97~7.87 (m, 4 H), 7.75~7.77 (m, 2 H),7.50 (t, J = 7.4 Hz, 2 H), 7.42 (t, J = 7.2 Hz, 1 H), 4.33 (t, J = 5.0 Hz, 2H), 3.84 (t, J = 5.0 Hz, 2 H).13C NMR (100 MHz, DMSO-d 6 ) 141.8, 138.8, 135.9,134.3, 129.6, 128.7, 127.3, 124.2, 122.7, 121.4, 59.6, 52.7. ESI-HRMS (m/z):Calcd. for C17H17N2O+: 265.1335. Found: 265.1347。
Example 3: r = R1, X = BF4Preparation of imidazole salt (denoted as IC-3) when n =4
The method specifically comprises the following steps: using dichloromethane as solvent, compound c (R = R1, X1= I, n =4) and compound d (X2= BF)4) Mixing at a molar ratio of 1:1.5, stirring at room temperature for 48h, filteringA white powder was obtained in 78% yield.
Example 4: r = R4, X = PF6Preparation of imidazole salt (denoted as IC-4) when n =3
The method specifically comprises the following steps: using dichloromethane as solvent, compound c (R = R4, X1= I, n =3) and compound d (X2= PF)6) Mixing according to a molar ratio of 1:2, stirring at normal temperature for 36h, and filtering to obtain yellow powder with a yield of 81%.
Example 5: preparation of imidazole salt (denoted as IC-5) with R = R2, X = TFSI, n =5
The method specifically comprises the following steps: compound c (R = R2, X1= I, n =5) and compound e were mixed in a molar ratio of 1:1.2 using water as a solvent, stirred at room temperature for 40h, and filtered to give a white powder with a yield of 81%.
Example 6: preparation of imidazole salt (denoted as IC-6) when R = R3, X = SCN, and n =6
The method specifically comprises the following steps: compound c (R = R3, X1= I, n =6) and compound d (X2= SCN) were mixed in a molar ratio of 1:1.6 using dichloromethane as a solvent, stirred at normal temperature for 38h, and filtered to obtain a white powder with a yield of 83%.
Example 7: preparation of imidazole salt (denoted as IC-7) with R = R3, X = Cl, and n = 7
The method specifically comprises the following steps: mixing a compound a (R = R2) and a compound b (X1 = Cl, n =2) in a molar ratio of 1:1.6 by using n-propanol as a solvent, adding the mixture to react at 70 ℃ for 35 hours, pouring the mixed solution after the reaction into anhydrous ether, generating a precipitate, and performing suction filtration and washing to obtain a white solid product with the yield of 84%.
Example 8: preparation of imidazole salt (noted as IC-8) with R = R2, X = Br, and n =8
The method specifically comprises the following steps: mixing a compound a (R = R2) and a compound b (X1 = Br, n =8) in a molar ratio of 1:1.8 by taking n-propanol as a solvent, adding the mixture into anhydrous ether for reacting at 78 ℃ for 39 hours, pouring the reacted mixture into the anhydrous ether, generating a precipitate, and performing suction filtration and washing to obtain a white solid product with the yield of 84%.
Example 9: preparation of imidazole salt (noted as IC-9) with R = R1, X = Br, and n =8
The method specifically comprises the following steps: mixing compound a (R = R1) and compound b (X1 = Br, n =8) in a molar ratio of 1:1.3 by using n-propanol as a solvent, adding the mixture to react at 79 ℃ for 42 hours, pouring the mixed solution after the reaction into anhydrous ether, generating a precipitate, and performing suction filtration and washing to obtain a white solid product with the yield of 81%.
Example 10: preparation of imidazole salt (noted as IC-10) with R = R4, X = I, and n =4
The method specifically comprises the following steps: mixing compound a (R = R1) and compound b (X1 = I, n =4) in a molar ratio of 1:1.5 by using n-propanol as a solvent, adding the mixture to react at 74 ℃ for 43 hours, pouring the reacted mixture into anhydrous ether, generating precipitate, and performing suction filtration washing to obtain a yellow solid with the yield of 82%.
Example 11: application of imidazole salt of IC-1 in perovskite solar cell when R = R3, X = I and n =2
The imidazolium salt prepared in example 1 was assembled into a perovskite solar cell according to standard methods, and the hydroxyl functionalized imidazolium salt was dissolved in trifluoroethanol solution and after sufficient dissolution, a clear transparent solution was obtained. And then soaking the FTO conductive glass subjected to ozone treatment in the solution for 16 h, taking out, washing molecules physically adsorbed on the surface of the FTO by using trifluoroethanol, and drying by using a nitrogen gun. Then spin coating perovskite, the perovskite used is CH3NH3PbI3After the perovskite thin film is sintered, a hole transport layer Spiro-OMeTAD is coated in a spinning mode, and then a layer of gold electrode is evaporated. The work function of FTO modified by imidazole salt IC-1 is-4.44 eV. The current-voltage of the perovskite solar cell is measured under the AM 1.5 simulated sunlight intensity (J-V) Curve (shown in blue curve of fig. 1) to obtain the open circuit photovoltage (V oc) 1.077V, short circuit photocurrent: (J sc) Is 20.88 mA cm-2Fill factor: (FF) Is 0.711, the energy conversion efficiencyη) It was 15.99%. By way of contrast, open circuit photovoltage of a perovskite solar cell without surface modification of FTO(s) ((s))V oc) 0.977V, short circuit photocurrent: (J sc) Is 15.32 mA cm-2Fill factor: (FF) Is 0.602, energy conversion efficiency: (η) It was 9.01% (black curve in FIG. 1).
Example 12: application of imidazole salt of IC-2 in perovskite solar cell when R = R2, X = I and n =2
The imidazolium salt prepared in example 2 was assembled into a perovskite solar cell according to standard methods, and the hydroxyl functionalized imidazolium salt was dissolved in trifluoroethanol solution and after sufficient dissolution, a clear transparent solution was obtained. And then soaking the FTO conductive glass subjected to ozone treatment in the solution for 15 h, taking out, washing molecules physically adsorbed on the surface of the FTO by using trifluoroethanol, and drying by using a nitrogen gun. Then spin coating perovskite, the perovskite used is CH3NH3PbI3After the perovskite thin film is sintered, a hole transport layer Spiro-OMeTAD is coated in a spinning mode, and then a layer of gold electrode is evaporated. The work function of FTO modified by imidazole salt IC-2 is-4.40 eV. The current-voltage of the perovskite solar cell is measured under the AM 1.5 simulated sunlight intensity (J-V) Curve (shown in red curve of fig. 1) to obtain the open circuit photovoltage (V oc) 1.082V, short circuit photocurrent: (J sc) Is 22.40 mA cm-2Fill factor: (FF) Is 0.714, the energy conversion efficiency: (η) The content was 17.31%. By way of contrast, open circuit photovoltage of a perovskite solar cell without surface modification of FTO(s) ((s))V oc) 0.977V, short circuit photocurrent: (J sc) Is 15.32 mA cm-2Fill factor: (FF) Is 0.602, energy conversion efficiency: (η) It was 9.01% (black curve in FIG. 1).

Claims (7)

1. A hydroxyl functionalized imidazolium salt is characterized in that a terminal is hydroxyl, imidazole is used as a core, an aromatic ring is substituted on an imidazole N atom, an anion is halogen or halogen-like, and the specific structural formula is as follows:
Figure DEST_PATH_IMAGE001
Figure 587887DEST_PATH_IMAGE002
wherein: r is a compound of the structure shown by R1, R2, R3 or R4; x is Cl, Br, I, SCN, BF4、PF6Or TFSI; n =2~ 8.
2. The hydroxyl-functionalized imidazolium salt according to claim 1, characterized by being one of the following:
r = R3, X = I, n =2, imidazole salt as IC-1;
r = R2, X = I, n =2, imidazole salt as IC-2;
R = R1，X = BF4n =4, imidazole salt as IC-3;
R = R4，X = PF6n =3, imidazole salt IC-4;
r = R2, X = TFSI, n =5, imidazole salt as IC-5;
r = R3, X = SCN, n =6, imidazole salt as IC-6;
r = R3, X = Cl, n = 7, imidazole salt as IC-7;
r = R2, X = Br, n =8, imidazole salt as IC-8:
r = R1, X = Br, n =8, imidazole salt as IC-9;
r = R4, X = I, n =4, and the imidazole salt is denoted IC-10.
3. A process for the preparation of the hydroxyl-containing functionalized imidazolium salt according to claim 1, wherein the synthetic route is as follows:
Figure DEST_PATH_IMAGE003
the method comprises the following specific steps: taking n-propanol as a solvent, mixing a compound (a) and a compound (b): halogen-substituted alcohols, in a molar ratio of 1: (0.8-1.2), and reacting at 60-80 ℃ for 24-48 h to obtain a final product, which is marked as c; wherein, in the compound (a), R is R1, R2, R3 or R4; in compound (b), X = Cl, Br or I; n =2~ 8.
4. The process for the preparation of hydroxyl-containing functionalized imidazolium salts according to claim 3, further characterized by the following synthetic route:
Figure 239448DEST_PATH_IMAGE004
the method comprises the following specific steps: using dichloromethane as solvent, mixing compound (c) and compound (d): NaX2According to the molar ratio of 1: (1-2) mixing, and reacting for 20-48 hours through ion exchange to obtain a final product, which is marked as e; in the compound (d), X is BF4、PF6Or SCN.
5. The process for the preparation of hydroxyl-containing functionalized imidazolium salts according to claim 3, further characterized by the following synthetic route:
Figure DEST_PATH_IMAGE005
the method comprises the specific steps of taking water as a solvent, mixing a compound (c) and a compound f: L iTFSI according to a molar ratio of 1 (1-2), and reacting for 20-48 hours through ion exchange to obtain a final product, wherein the final product is marked as g.
6. The use of the hydroxyl-containing imidazolium salt of claim 1 in a perovskite solar cell, by: hydroxyl functionalized imidazolium salt is used as an interface modification layer, then self-assembled on the surface of an FTO conductive substrate by a soaking method, and the FTO modified by an ionic conductor is applied to a perovskite solar cell as the conductive substrate, so that excellent photovoltaic performance can be obtained without an electronic transmission material.
7. The use of the hydroxyl-containing imidazolium salt according to claim 6 in perovskite solar cells, by: dissolving hydroxyl functionalized imidazole salt in a trifluoroethanol solution, and obtaining a transparent and clear solution after full dissolution; then soaking the FTO conductive glass subjected to ozone treatment in the solution for 8-24 h, and taking outWashing molecules physically adsorbed on the surface of the FTO by using trifluoroethanol, and drying by using a nitrogen gun; then spin coating perovskite, the perovskite used is CH3NH3PbI3After the perovskite thin film is sintered, a hole transport layer Spiro-OMeTAD is coated in a spinning mode, and then a layer of gold electrode is evaporated.
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Application publication date: 20200728