CN113512178A - N-type pyrrolopyrrolidinone COF (COF) dendritic conjugated polymer electrolyte cathode interface layer and preparation method thereof - Google Patents
N-type pyrrolopyrrolidinone COF (COF) dendritic conjugated polymer electrolyte cathode interface layer and preparation method thereof Download PDFInfo
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 2
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Abstract
The invention discloses an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer and a preparation method thereof, wherein bromo-pyrrolopyrrolidinone derivatives and tri (4-chloronicotinyl borate phenyl) amine are synthesized into a conjugated polymer through a coupling reaction, and then the conjugated polymer is ionized to obtain a product. Firstly, a COF-like two-dimensional dendritic conjugated polymer with alkyl quaternary ammonium salt introduced into a side chain enables the material to have unique charge transmission performance of a COF material, and carrier mobility of a device is improved; secondly, lone pair electrons on nitrogen atoms in triphenylamine are transferred to pyrrolopyrrolidone to form favorable n-type autodoping effect, so that the conductivity of the material is improved; and finally, the dendritic polymer is self-assembled into an ordered arrangement due to strong interface interaction between the dendritic polymer and the lower substrate, the morphology of the active layer is optimized, and the mobility of the current carrier is improved, so that the short-circuit current and the filling factor of the device are improved, and the efficiency of the device is finally improved.
Description
Technical Field
The invention relates to the technical field of cathode interface layers of organic solar cells, in particular to a preparation method of an n-type pyrrolopyrrolidinone COF (chip on film) dendritic conjugated polymer electrolyte cathode interface layer.
Background
With the development of the times, the nonrenewable resources on the earth are less and less. With the large amount of exploitation and use of fossil energy, the problem of environmental pollution on the earth is also getting more and more serious. The research of green renewable energy becomes a new development trend and is paid attention by researchers in various fields. Solar energy is one of the most ideal green renewable energy sources on the earth, has the characteristics of inexhaustibility, zero pollution and low risk, and rapidly becomes a research hotspot of green renewable energy sources in recent years. At present, scientists are continuously researching how to develop and utilize solar energy, and the most convenient and most effective method can be basically used for preparing solar cells.
Scientists have conducted intensive research into solar cells to date. Inorganic solar cells are the most widely used in the market at present, account for more than 80% in the solar cell industry, and are the most popular of monocrystalline silicon solar cells and polycrystalline silicon solar cells. The battery has excellent performance, and the photoelectric conversion efficiency is at a higher level and almost reaches the theoretical efficiency (30%). However, in practical operation, the problems of high cost, high energy consumption, high pollution and the like in the production process have to be considered, for example, the Si-based solar cell has a complex process for controlling and synthesizing the monocrystalline silicon and high energy consumption, which leads to the high price of the crystalline silicon solar cell in the market, and is also a main reason for limiting the application and development thereof. The organic solar cell has the characteristics of low cost, simple production process, light weight, flexibility and the like, and has become a research hotspot in the field of solar cells.
However, organic solar cells have lower photoelectric conversion efficiency and light absorption rate and poor stability as compared with inorganic solar cells. Based on the above points, scientists have developed a lot of experimental studies, and have adopted many methods to solve the above problems, such as studying new active layer materials, interface modification, active layer doping, studying new transport layer materials, interface self-assembly, etc. The effect of improving the performance of the solar cell by utilizing interface modification is obvious. By the interface modification method, the contact among all layers of the photovoltaic device can be enhanced, and the carrier mobility is improved, so that the photovoltaic performance is improved. With the progress of science and technology, the improvement of preparation technology and the research of new materials, the device efficiency of the organic solar cell is greatly improved, and the development and the application of the organic solar cell are better and better. With the continuous research and development of novel efficient donor materials and interface layer materials and the continuous optimization of device structures, the device efficiency of a single-section non-fullerene organic solar cell exceeds 18%.
However, there is still a large distance from the demand for commercial large-area production of organic solar cell devices in terms of efficiency, stability of the devices in air, and thickness sensitivity. In order to keep the distance from commercial production closer, researchers turned their attention to organic non-fullerene solar cells. At present, the main obstacles for improving the efficiency of a non-fullerene solar cell are three difficult problems of non-ideal appearance of an active layer, low carrier mobility and existence of an interface barrier between the active layer and an electrode. As a result of extensive studies, it is particularly important to appropriately modify the interface between the electrode and the active layer, i.e., to interpose an appropriate cathode interface layer between the electrode and the active layer, in order to improve the photoelectric conversion efficiency of the solar cell.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a preparation method of an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer and application of the n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer in a non-fullerene solar cell. Conventional cathode interface layers mainly include metal fluorides, n-type metal oxides, organic small molecules, organic small molecule electrolytes, polymer electrolytes, fullerene derivatives, and the like. The existing cathode interface layer has single function and can not simultaneously solve the three problems of the morphology of an active layer, the electron mobility and the interface barrier. The n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer designed by the invention has a plurality of advantages. Firstly, a COF-like two-dimensional hyperbranched conjugated polymer electron transport layer prepared by introducing flexible alkyl quaternary ammonium salt into a side chain enables the material to have a unique porous structure of a COF material and excellent charge transport performance, and carrier mobility of a device is improved. The alkyl quaternary ammonium salt side chain engineering can also ensure that certain interaction exists between COF layers and COF excessive aggregation is prevented, and the COF material has high conductivity and high carrier mobility and also has excellent solution processing performance. The introduction of the flexible alkyl quaternary ammonium salt can also improve the solubility and the film forming property of the material. Secondly, due to the existence of groups such as side chain polar quaternary ammonium salt and main chain and side chain polar N and F atoms, not only can an interface dipole be formed and an interface potential barrier be reduced, but also lone-pair electrons on the N atom can be transferred to the main chain of the conjugated polymer to form N-type autodoping. The n-type self-doping can further form larger interface dipoles, the double dipoles can greatly reduce charge injection potential barriers, improve carrier mobility, and avoid the reduction of device stability caused by ion migration like external doping. Meanwhile, the weak bond self-assembly performance of the C-N … N and the C-N … H can also optimize the appearance of an electron transport layer and induce the self-assembly of an active layer; thirdly, by designing a self-assembled dendritic hyperbranched COF-like two-dimensional structure, the density of polar side chains can be improved, the interaction between the electron transport layer and the substrate is greatly enhanced, the interface dipole moment is improved, the self-assembly of the electron transport layer into an ordered micro-morphology is induced again, and the interface regulation and control capability of the electron transport layer and the self-assembly of the induced active layer are greatly improved; and finally, improving the conductivity of the material by introducing an n-type autodoping effect and a COF-like structure, and obtaining an electronic transmission layer material with insensitive thickness. Meanwhile, compared with external doping, the n-type self-doping introduced by the project can reduce ion migration and improve the stability of the device. Thickness insensitivity and stability are important conditions that will be necessary for future large-scale commercial roll-to-roll printing production. The n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer designed and synthesized by the project can simultaneously solve the problems of poor appearance of an active layer, low carrier mobility and thickness sensitivity, and can realize environment-friendly printing and processing of water/alcohol soluble solution.
The invention aims to provide a preparation method and application of an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer. The non-fullerene solar cell device is prepared by the n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer.
The technical scheme adopted by the invention is as follows: an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer, which is characterized in that: has a structure shown in formula I, and comprises the following components:
the other technical scheme of the invention is as follows: an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer containing a structure shown in formula I is characterized by comprising the following steps:
the method comprises the following steps: synthesizing a COF-like dendritic conjugated polymer PTPADPPBr;
(1) to a dried 100mL reaction flask was added 0.75mmol of 2, 5-bis- (6-bromo-hexyl) -3, 6-bis- (5-bromo-thiophen-2-yl) -2, 5-dihydro-pyrrolo [3,4-c ]]Pyrrole-1, 4-dione (DPPBr) and 0.5mmol of tris (4-boroxinol phenyl) amine, 138.21mg K2CO3And 2.5mL of deionized water, and 10mg of Pd (dppf) Cl catalyst was added2And 3 drops of phase transfer catalyst methyl trioctyl ammonium chloride (Aliguat 336), pumped under vacuum with nitrogen for about 5-6 times, and treated with N2Replacing air in the reaction bottle;
(2) then, under the protection of nitrogen atmosphere, 10mL of toluene is injected into a polymerization bottle, the mixture is heated to 100 ℃, and reflux reaction is carried out at 100 ℃ for 25 min;
(3) after the reaction is finished, pouring the mixture into 500mL of methanol under strong stirring, magnetically stirring for 12h, repeating the operation for 3 times, and then performing suction filtration to obtain a crude product;
(4) the crude product is subjected to Soxhlet extraction and purification by sequentially using methanol, acetone and chloroform, the solution obtained after final chloroform extraction is taken for rotary evaporation to obtain a product, the product is placed in a vacuum drying oven, vacuum drying is carried out for 24 hours at 50 ℃, and finally a blue solid is obtained, wherein the yield is 56%.
Step two: synthesizing a COF-like dendritic conjugated polymer electrolyte cathode interface layer PTPADPPNBr;
(1) under the protection of nitrogen, 500mg of the first-step product PTPADPPBr is dissolved in 100mL of tetrahydrofuran;
(2) cooling the reaction system to-78 ℃ by using liquid nitrogen, dropwise adding 9.0mL of 13% THF solution and 2mol/L of trimethylamine THF solution into the mixed solution through a constant-pressure dropping funnel, stirring for reacting for 5 days, once solids are separated out, dropwise adding 3mL of methanol for dissolving, and supplementing 2mL of trimethylamine every day to promote the completion of the ionization reaction;
(3) after the reaction is finished, removing the solvent by rotary evaporation, dissolving the obtained solid by using methanol, filtering, removing a product which is insoluble in the methanol and is not completely ionized, and carrying out rotary drying again to obtain a crude product;
(4) and performing Soxhlet extraction and purification on the crude product by sequentially using acetone, normal hexane and chloroform, purifying the chloroform, dialyzing by using a dialysis bag with the cut-off value of 3500g/mol to remove low-molecular-weight oligomers, and performing vacuum drying for 24 hours to obtain a purple black solid with the yield of 92%.
The other technical scheme of the invention is as follows: a non-fullerene solar cell device of an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer is characterized in that:
comprises an ITO glass layer, an n-type pyrrolopyrrolidinone COF conjugated polymer electrolyte cathode interface layer arranged on the ITO glass layer, an active layer arranged on the n-type pyrrolopyrrolidinone COF conjugated polymer electrolyte cathode interface layer, and MoO arranged on the active layer3Layer, set at the MoO3An Ag electrode layer on the layer.
The other technical scheme of the invention is as follows: a method for synthesizing an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer PTPADPPNBr is characterized in that: the reaction equation of the specific synthetic route is as follows:
compared with the prior art, the invention has the beneficial effects that:
(1) the method has strong innovation, and integrates the four advantages of high conductivity and high electron mobility of COF-like materials, n-type self-doping effect, dendritic hyperbranched conjugated polymer induced self-assembly and environment-friendly water/alcohol-soluble processing.
(2) Can simultaneously solve three problems of non-ideal appearance of the active layer, low carrier mobility and interface potential barrier between the active layer and the electrode. The method comprises the following specific steps: firstly, a flexible alkyl quaternary ammonium salt is introduced into a side chain to prepare a COF-like two-dimensional hyperbranched conjugated polymer, so that the COF-like two-dimensional hyperbranched conjugated polymer is ensured to have a certain pi-pi interaction without excessive aggregation, the conductivity and the solubility of the COF-like two-dimensional hyperbranched conjugated polymer are balanced, and the COF-like two-dimensional hyperbranched conjugated polymer is ensured to have excellent charge transmission performance and good solubility of the quaternary ammonium salt. Secondly, due to the weak bond induction self-assembly of C-N … N and C-N … H between the main chain and the side chain, the interaction between the N atoms of the main chain and the side chain and the electrode substrate and even the active layer and the interaction between the polar group of the side chain and the substrate can form an interface dipole, reduce the interface potential barrier, form ohmic contact and improve the transmission efficiency of charges; thirdly, the interaction between the electron transmission layer and the substrate can be greatly enhanced by utilizing the dendritic hyperbranched structure, and the electron transmission layer is self-assembled to form a face-on arrangement morphology beneficial to charge transmission by utilizing a double induction effect, so that the electron transmission layer is further used as a template to induce the non-fullerene active layer to form a part or all of a face-on structure.
(3) Lone pair electrons of nitrogen on the quaternary ammonium salt and the triphenylamine can be transferred to the main chain of the electron-withdrawing pyrrolopyrrolidinone to form an n-type self-doping effect, and the n-type self-doping effect is beneficial to forming a large interface dipole and improving the conductivity of the material, so that the open-circuit voltage and the short-circuit current of the device are improved. And the stability of the device can be prevented from being damaged by ion migration caused by external doping, and an electronic transmission layer insensitive to thickness is obtained, thereby laying a foundation for realizing large-area roll-to-roll solution printing production in the future.
(4) The prior art only uses common conjugated polymer electrolyte, fullerene derivative, inorganic zinc oxide and the like as cathode interface layers, and the cathode interface layers cannot simultaneously solve the problems of large interface barrier, low carrier mobility and poor appearance of an active layer between the active layer and an electrode. The four advantages of dendritic hyperbranched conjugated polymer induced self-assembly, n-type self-doping effect, COF-like material and environment-friendly water/alcohol-soluble processing can not be gathered.
Drawings
Fig. 1 is a structural diagram of an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer ptpadpnbr according to the present invention.
Fig. 2 is a device structure diagram of an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer ptpadpnbr according to the present invention.
Fig. 3 is a specific reaction equation diagram of an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer ptpadpnbr according to the present invention.
Detailed Description
The invention is further described below with reference to the accompanying drawings.
The reaction equation of the invention is shown in figure 3, and the specific reaction steps are as follows: the synthesis method of the n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer PTPADPPNBr comprises the following steps:
the method comprises the following steps: synthesizing a COF-like dendritic conjugated polymer PTPADPPBr;
(1) to a dried 100mL reaction flask was added 0.75mmol of 2, 5-bis- (6-bromo-hexyl) -3, 6-bis- (5-bromo-thiophen-2-yl) -2, 5-dihydro-pyrrolo [3,4-c ]]Pyrrole-1, 4-dione (DPPBr) and 0.5mmol of tris (4-boroxinol phenyl) amine, 138.21mg K2CO3And 2.5mL of deionized water, and 10mg of Pd (dppf) Cl catalyst was added2And 3 drops of phase transfer catalyst methyltrioctylchlorinationAmmonium (Aliguat 336), evacuating with nitrogen gas and evacuating about 5-6 times, and adding N2The air in the reaction flask was displaced.
(2) Subsequently, 10mL of toluene were injected into the polymerization flask under a nitrogen atmosphere, the mixture was heated to 100 ℃ and the reaction was refluxed at 100 ℃ for 25 min.
(3) After the reaction is finished, pouring the mixture into 500mL of methanol under strong stirring, magnetically stirring for 12h, repeating the operation for 3 times, and then performing suction filtration to obtain a crude product;
(4) the crude product is subjected to Soxhlet extraction and purification by sequentially using methanol, acetone and chloroform, the solution obtained after final chloroform extraction is taken for rotary evaporation to obtain a product, the product is placed in a vacuum drying oven, vacuum drying is carried out for 24 hours at 50 ℃, and finally a blue solid is obtained, wherein the yield is 56%.
Step two: synthesis of COF-like dendritic conjugated polymer electrolyte cathode interface layer ptpadpnbr:
(1) under the protection of nitrogen, 500mg of the first-step product PTPADPPBr is dissolved in 100mL of tetrahydrofuran;
(2) cooling the reaction system to-78 ℃ by using liquid nitrogen, dropwise adding 9.0mL of 13% THF solution and 2mol/L of trimethylamine THF solution into the mixed solution through a constant-pressure dropping funnel, stirring for reacting for 5 days, once solids are separated out, dropwise adding 3mL of methanol for dissolving, and supplementing 2mL of trimethylamine every day to promote the completion of the ionization reaction;
(3) after the reaction is finished, removing the solvent by rotary evaporation, dissolving the obtained solid by using methanol, filtering, removing a product which is insoluble in the methanol and is not completely ionized, and carrying out rotary drying again to obtain a crude product;
(4) and performing Soxhlet extraction and purification on the crude product by sequentially using acetone, normal hexane and chloroform, purifying the chloroform, dialyzing by using a dialysis bag with the cut-off value of 3500g/mol to remove low-molecular-weight oligomers, and performing vacuum drying for 24 hours to obtain a purple black solid with the yield of 92%.
The invention has the beneficial effects that: the invention discloses a preparation method of an n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer, which comprises the steps of synthesizing a conjugated polymer by coupling reaction of a bromo-pyrrolopyrrolidinone derivative and tri (4-chloronicotinyl borate phenyl) amine, and ionizing to obtain a product. Firstly, a COF-like two-dimensional dendritic conjugated polymer with alkyl quaternary ammonium salt introduced into a side chain enables the material to have unique charge transmission performance of a COF material, and carrier mobility of a device is improved; secondly, lone pair electrons on nitrogen atoms in triphenylamine are transferred to pyrrolopyrrolidone to form favorable n-type autodoping effect, so that the conductivity of the material is improved, and the problem of interface layer thickness sensitivity is solved; and finally, the dendritic polymer is self-assembled into an ordered arrangement due to strong interface interaction between the dendritic polymer and the lower substrate, the morphology of the active layer is optimized, and the mobility of the current carrier is improved, so that the short-circuit current and the filling factor of the device are improved, and the efficiency of the device is finally improved.
Claims (6)
1. An n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte cathode interface layer, which is characterized in that: has a structure shown in formula I, and comprises the following components:
2. a method for preparing a cathode interface layer containing the n-type pyrrolopyrrolidinone COF dendritic conjugated polymer electrolyte according to claim 1, comprising the steps of:
the method comprises the following steps: synthesizing a COF-like dendritic conjugated polymer PTPADPPBr;
step two: and (3) synthesizing a COF-like dendritic conjugated polymer electrolyte cathode interface layer PTPADPPNBr.
3. The method for preparing the cathode interface layer of the n-type pyrrolopyrrolidinone-containing COF dendritic conjugated polymer electrolyte according to claim 2, wherein: the synthesis of the COF-like dendritic conjugated polymer PTPADPPBr comprises the following specific steps:
(1) to a dried 100mL reaction flask was added 0.75mmol of 2, 5-bis- (6-bromo-hexyl) -3, 6-bis- (5-bromo-thiophen-2-yl) -2, 5-dihydro-pyrrolo [3,4-c ]]Pyrrole-1, 4-diketone (DPPBr) and 0.5mmol of tris (4-boroxine phenyl) amine, 138.21mg K2CO3And 2.5mL of deionized water, and 10mg of Pd (dppf) Cl catalyst was added2And 3 drops of phase transfer catalyst methyl trioctyl ammonium chloride (Aliguat 336), pumped under vacuum with nitrogen for about 5-6 times, and treated with N2Replacing air in the reaction bottle;
(2) then, under the protection of nitrogen atmosphere, 10mL of toluene is injected into a polymerization bottle, the mixture is heated to 100 ℃, and reflux reaction is carried out at 100 ℃ for 25 min;
(3) after the reaction is finished, pouring the mixture into 500mL of methanol under strong stirring, magnetically stirring for 12h, repeating the operation for 3 times, and then performing suction filtration to obtain a crude product;
(4) the crude product is subjected to Soxhlet extraction and purification by sequentially using methanol, acetone and chloroform, the solution obtained after final chloroform extraction is taken for rotary evaporation to obtain a product, the product is placed in a vacuum drying oven, vacuum drying is carried out for 24 hours at 50 ℃, and finally a blue solid is obtained, wherein the yield is 56%.
4. The method for preparing the cathode interface layer of the n-type pyrrolopyrrolidinone-containing COF dendritic conjugated polymer electrolyte according to claim 2, wherein: the synthesis of COF-like dendritic conjugated polymer electrolyte cathode interface layer PTPADPPNBr comprises the following steps:
(1) under the protection of nitrogen, 500mg of the first-step product PTPADPPBr is dissolved in 100mL of tetrahydrofuran;
(2) cooling the reaction system to-78 ℃ by using liquid nitrogen, dropwise adding 9.0mL of 13% THF solution and 2mol/L of trimethylamine THF solution into the mixed solution through a constant-pressure dropping funnel, stirring for reacting for 5 days, once solids are separated out, dropwise adding 3mL of methanol for dissolving, and supplementing 2mL of trimethylamine every day to promote the completion of the ionization reaction;
(3) after the reaction is finished, removing the solvent by rotary evaporation, dissolving the obtained solid by using methanol, filtering, removing a product which is insoluble in the methanol and is not completely ionized, and carrying out rotary drying again to obtain a crude product;
(4) and performing Soxhlet extraction and purification on the crude product by sequentially using acetone, normal hexane and chloroform, purifying the chloroform, dialyzing by using a dialysis bag with the cut-off value of 3500g/mol to remove low-molecular-weight oligomers, and performing vacuum drying for 24 hours to obtain a purple black solid with the yield of 92%.
5. A non-fullerene solar cell device of an n-type pyrrolopyrrolidinone COF dendrimer conjugated polymer electrolyte cathode interfacial layer according to claim 1, wherein:
comprises an ITO glass layer, an n-type pyrrolopyrrolidinone COF conjugated polymer electrolyte cathode interface layer arranged on the ITO glass layer, an active layer arranged on the n-type pyrrolopyrrolidinone COF conjugated polymer electrolyte cathode interface layer, and MoO arranged on the active layer3Layer, set at MoO3An Ag electrode layer on the layer.
6. The synthesis method of the PTPADPPNBr of the cathode interface layer of the n-type pyrrolopyrrolidinone COF conjugated polymer electrolyte as claimed in claim 1, wherein the synthesis method comprises the following steps: the reaction equation of the specific synthetic route is as follows:
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