CN115109232A - Non-equivalent donor-acceptor unit conjugated polymer, preparation thereof and application thereof in polymer solar cell - Google Patents
Non-equivalent donor-acceptor unit conjugated polymer, preparation thereof and application thereof in polymer solar cell Download PDFInfo
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Abstract
The invention discloses an unequal donor-acceptor unit conjugated polymer, a preparation method thereof and application thereof in a polymer solar cell. The structural formula is shown as formula I. The invention provides a non-equivalent donor-acceptor unit medium band gap conjugated polymer material, which has great complementarity with a narrow band gap n-type small molecule acceptor material in absorption, has better charge transmission performance and proper electron energy level, can be used as an electron donor material to be matched with the narrow band gap n-type small molecule acceptor material, and is applied to polymer solar cell devices.
Description
Technical Field
The invention belongs to the technical field of organic synthesis and solar cells, and particularly relates to an unequal donor-acceptor unit conjugated polymer, a preparation method thereof and application thereof in a polymer solar cell.
Background
With the rapid development of society, the demand of energy sources is increased year by year, however, fossil fuels are limited, and the large-scale use of fossil fuels can cause environmental pollution, and the energy source problem is a major concern of nations in the world. There is a pressing need for new clean, renewable energy sources. Among them, solar energy has the advantages of inexhaustible, pollution-free, convenient use, etc., and is gradually becoming a substitute for new energy.
Solar cells that convert solar energy directly into electrical energy are an important form of solar energy utilization. Solar cells currently researched and developed include monocrystalline silicon, polycrystalline silicon, amorphous silicon, monocrystalline GaAs, organic-inorganic hybrid perovskite, organic/polymer solar cells, and the like. The first silicon-based batteries are commercialized, and the energy conversion efficiency of the first silicon-based batteries is about 20%, so that the first silicon-based batteries are commercialized. In recent years, organic/polymer solar cells based on solution processed organic/polymer photovoltaic materials are expected to be an important supplement to silicon-based solar cells in terms of flexible and translucent devices due to the outstanding advantages of simple device structure, low processing cost, light weight, and the like, and can be prepared into flexible and translucent devices. In addition, the organic materials are various in types and strong in designability, and the performance of the solar cell is hopefully improved through modification of the materials. Therefore, organic/polymer solar cell photovoltaic materials and devices are of great interest in scientific research and industrial development.
The active layer of the polymer solar cell is mainly composed of a conjugated polymer donor and an organic semiconductor acceptor blended film. The current widely used polymer donor photovoltaic materials are based on D-A copolymers with equal amount of donor-acceptor units arranged alternately, the modification improvement based on the equal amount of D-A copolymers mainly comprises side chain engineering, functional group substitution and the like, compared with the fixed equal proportion of the equivalent D-A copolymer, the unequal copolymer can realize the adjustment of various properties such as electron energy level, absorption spectrum, carrier mobility, crystallinity and the like by adjusting the proportion of a donor and an acceptor, the specific implementation method only needs to quantitatively control the charge ratio at the last step of the synthetic route, the adjustment of the material properties is made considerably easier and the most suitable properties for the receptor material can be found by trying in different proportions.
Disclosure of Invention
The invention aims to provide a non-equivalent amount of donor-acceptor unit D-A copolymer.
The structural formula of the unequal donor-acceptor unit D-A copolymer provided by the invention is shown as the formula I:
in the formula I, D represents a donor unit group and can be selected from one of the following structural formulas:
in the formula II-1 and the formula II-2, R is selected from any one of the following groups: alkyl, alkoxy, alkylthio, silyl and ester groups, wherein the alkyl contained in each group can be a linear or branched alkyl with 1-12 carbon atoms, and can be a linear or branched alkyl with C6-C12 specifically;
in formula I above, a represents an acceptor unit group, which may be selected from any one of the following structural formulae:
in the formulas III-1 and III-2, R is selected from any one of the following groups: alkyl, alkoxy, alkylthio, silyl and ester groups, wherein the alkyl contained in each group can be a linear or branched alkyl group having 1 to 12 carbon atoms; can be a straight chain or branched chain alkyl of C6-C12;
in the formula I, x is 0.1-0.75, specifically 0.1-0.3, 0.1, 0.2 or 0.3;
n is a natural number between 5 and 100.
The unequal donor-acceptor unit D-A copolymer provided by the invention can be specifically, but not limited to, the structure shown as follows:
the invention also provides a preparation method of the unequal donor-acceptor unit D-A copolymer.
The unequal amount of donor-acceptor unit D-A copolymer provided by the invention is prepared by a method comprising the following steps:
a one-pot method: in the presence of a catalyst, reacting 1 equivalent of compound 1, x equivalent of compound 2 and (1-x) equivalent of compound 3 to obtain an unequal amount of donor-acceptor unit D-A copolymer shown in formula I;
wherein x is 0.1-0.75, specifically 0.1-0.3, 0.1, 0.2, 0.25, 0.3, 0.4, 0.5 or 0.75;
in compounds 1 and 2, D represents a donor unit group, which may be selected from one of the following structural formulae:
wherein R is selected from any one of the following groups: alkyl, alkoxy, alkylthio, silyl and ester groups, wherein the alkyl contained in each group can be a linear or branched alkyl with 1-12 carbon atoms, and can be a linear or branched alkyl with C6-C12;
in compound 3, a represents an acceptor unit group and may be selected from any one of the following structural formulae:
r is selected from any one of the following groups: alkyl, alkoxy, alkylthio, silyl and ester groups, wherein the alkyl contained in each group can be a linear or branched alkyl group having 1 to 12 carbon atoms; in particular, the alkyl group can be a linear chain or branched chain alkyl group of C6-C12;
in the above method, the catalyst may be specifically palladium tetratriphenylphosphine;
the proportion of the catalyst to the compound 1 can be as follows: 20-80 mg: 1mmol of the active component;
the reaction is carried out in an organic solvent, wherein the organic solvent can be toluene, chlorobenzene, o-xylene, o-dichlorobenzene and the like;
the reaction is carried out under the protection of inert gas, and the inert gas can be specifically argon, nitrogen and the like;
the reaction conditions may be: heating and refluxing for 12-48 h.
The invention also provides a photoactive layer.
The photoactive layer provided by the invention comprises the unequal amount of the donor-acceptor unit D-A copolymer and an n-type electron acceptor, wherein the weight ratio of the n-type electron acceptor to the unequal amount of the donor-acceptor unit D-A copolymer can be 1: 0.5-2, and specifically can be 1: 1.4;
the n-type electron acceptor can be specifically a non-fullerene small molecule compound, such as Y6 shown in FIG. 1;
the photoactive layer is prepared by mixing the non-equivalent amount of the D-A copolymer as the donor-acceptor unit and the n-type electron acceptor in a solvent, and coating,
wherein the solvent may be selected from: at least one of toluene, xylene, trimethylbenzene, chloroform, chlorobenzene, dichlorobenzene, and trichlorobenzene;
in the mixture, the concentration of the non-equivalent donor-acceptor unit D-A copolymer can be 0.5mg/mL to 50mg/mL, specifically 4mg/mL to 20mg/mL, and the concentration of the n-type electron acceptor can be 0.5mg/mL to 50mg/mL, specifically 3mg/mL to 20 mg/mL.
The use of the aforementioned unequal donor-acceptor unit D-A copolymers or photoactive layers made from the aforementioned unequal donor-acceptor unit D-A copolymers in the following functional energy devices is also within the scope of the present invention.
The functional performance measuring device may specifically be: a thin film semiconductor device, a light detecting device, a polymer solar cell device, or a photoelectric device.
The invention also provides a polymer solar cell device.
The invention provides a polymer solar cell device, which comprises: a bottom electrode, a top electrode, and at least one organic semiconductor photovoltaically active layer disposed between the two electrodes, the organic semiconductor photovoltaically active layer comprising the non-equivalent amount of donor-acceptor unit D-A copolymer and an organic semiconductor acceptor material.
The organic semiconductor acceptor material may specifically be a non-fullerene acceptor Y6.
The invention provides a non-equivalent donor-acceptor unit medium band gap conjugated polymer material, which has great complementarity with a narrow band gap n-type small molecule acceptor material in absorption, has better charge transmission performance and proper electron energy level, can be used as an electron donor material to be matched with the narrow band gap n-type small molecule acceptor material, and is applied to polymer solar cell devices.
The non-equivalent donor-acceptor unit conjugated polymer has the advantages of simple synthesis steps and high yield, and the prepared polymer solar cell device has the advantages of wide spectral response range, high open-circuit voltage, high short-circuit current and high filling factor, and is expected to be applied to the commercialization of the polymer solar cell.
The invention provides a D-A copolymer based on unequal donor-acceptor units for the first time, and the polymer can finely and flexibly adjust and improve various photophysical and photochemical properties such as energy level, absorption, crystallinity and the like of the polymer by adjusting the proportion of the donor units and the acceptor units so as to better adapt to an acceptor material and improve the energy conversion efficiency of an organic solar cell.
Drawings
FIG. 1 is a schematic diagram of the molecular structure of a non-fullerene acceptor Y6 used in the present invention.
FIG. 2 shows absorption spectra of polymers PM6-D1, PM6-D2, and PM6-D3 prepared in examples 1, 2, and 3 according to the present invention in chloroform solution and thin film state.
FIG. 3 is a cyclic voltammogram graph corresponding to the polymers PM6-D1, PM6-D2, and PM6-D3 prepared in examples 1, 2, and 3 of the present invention.
FIG. 4 is a J-V curve of polymer solar cell devices prepared by blending the polymers PM6-D1, PM6-D2, PM6-D3 and Y6 prepared in examples 1, 2 and 3 of the invention.
FIG. 5 is a graph of external quantum efficiency of polymer solar cell devices prepared by blending the polymers PM6-D1, PM6-D2, PM6-D3 and Y6 prepared in examples 1, 2 and 3 of the invention.
FIG. 6 shows an absorption spectrum of polymer J52-F-D1 in chloroform prepared in inventive example 4.
Detailed Description
The present invention will be described below with reference to specific examples, but the present invention is not limited thereto.
The experimental methods used in the following examples are all conventional methods unless otherwise specified; reagents, materials and the like used in the following examples are commercially available unless otherwise specified.
The pressures used in the following examples are at or near atmospheric. All solvents used were purchased as HPLC grade and all reactions were carried out under an inert atmosphere of argon, all reagents and starting materials being commercially available unless otherwise indicated.
Example 1 Synthesis of Polymer of formula PM6-D1
The reaction was carried out according to the above reaction equation, taking monomers M1, M2 and M30.3mmol, 0.03mmol and 0.27mmol respectively, dissolving them in toluene (8mL) solvent, evacuating with argon for 5 minutes, adding catalyst tetrakis (triphenylphosphine) palladium (0) (15mg), evacuating for 25 minutes, then reacting at toluene reflux temperature for 24 hours and stopping. The polymer solution was cooled to room temperature, slowly precipitated and poured into methanol (50mL), and the precipitated solid polymer was eluted with methanol and n-hexane in sequence in a soxhlet extractor. Finally, the polymer was dissolved in chloroform and precipitated into methanol, filtered and dried under vacuum for one day to give a black solid powder of the polymer represented by the formula PM6-D1 with a yield of 95%.
The proportion of the donor unit and the acceptor unit in the obtained product can be verified by an element analysis test method.
The following are the polymer PM6-D1 elemental analysis test results: theoretically calculating the mass percentage of part of elements in PM6-D1: 66.81% for C, 6.43% for H and 20.98% for S. The actual measured ratio: c66.74%, H6.42, and S20.92. Within error, the product was confirmed to be the ratio described by the structural formula.
Example 2 Synthesis of Polymer of formula PM6-D2
The reaction is carried out according to the reaction equation, taking the monomers M1, M2 and M30.3mmol, 0.06mmol and 0.24mmol respectively, dissolving the monomers in toluene (8mL) solvent, exhausting air with argon for 5 minutes, adding the catalyst tetrakis (triphenylphosphine) palladium (0) (15mg), exhausting air for 25 minutes, and stopping after reacting for 24 hours at the reflux temperature of toluene. The polymer solution was cooled to room temperature, slowly precipitated and poured into methanol (50mL), and the precipitated solid polymer was eluted with methanol and n-hexane in sequence in a soxhlet extractor. Finally, the polymer was dissolved in chloroform and precipitated into methanol, filtered and dried under vacuum for one day to give a black solid powder of the polymer represented by the formula PM6-D2 with a yield of 93%.
Elemental analysis test results for Polymer PM6-D2: theoretically calculating the mass percentage of part of elements in PM6-D2: 66.78% for C, 6.43% for H and 20.97% for S. And (3) actual test results: c66.64%, H6.36%, and S20.68%.
Example 3 Synthesis of Polymer of formula PM6-D3
The reaction was carried out according to the above reaction equation, taking monomers M1, M2 and M30.3mmol, 0.09mmol,0.21mmol, respectively, dissolving them in toluene (8mL) solvent, evacuating with argon for 5 minutes, adding catalyst tetrakis (triphenylphosphine) palladium (0) (15mg), evacuating for 25 minutes, then reacting at toluene reflux temperature for 24 hours, and stopping. The polymer solution was cooled to room temperature, slowly precipitated and poured into methanol (50mL), and the precipitated solid polymer was eluted with methanol and n-hexane in sequence in a soxhlet extractor. Finally, the polymer was dissolved in chloroform and precipitated into methanol, filtered and dried under vacuum for one day to give a black solid powder of the polymer represented by the formula PM6-D3 with a yield of 97%.
Elemental analysis test results for Polymer PM6-D3: theoretically calculating the mass percentage of part of elements in PM6-D3: 66.74% for C, 6.42% for H and 20.96% for S. The actual measured results are: 66.53% for C, 6.44% for H and 21.10% for S.
Example 4 Synthesis of Polymer of formula J52-F-D1
The reaction was carried out according to the above reaction equation, taking monomers M1, M2 and M40.3mmol, 0.06mmol,0.24mmol respectively, dissolving them in a mixed solvent of toluene (8mL) and DMF (2mL), evacuating with argon for 5 minutes, adding catalyst tetrakis (triphenylphosphine) palladium (0) (15mg), evacuating for 25 minutes, and then reacting at toluene reflux temperature for 24 hours and stopping. The polymer solution was cooled to room temperature, slowly precipitated and poured into methanol (50mL), and the precipitated solid polymer was eluted with methanol and n-hexane in sequence in a soxhlet extractor. Finally dissolving the polymer by using trichloromethane, precipitating the polymer into methanol, filtering the solution, and drying the solution in vacuum for one day to obtain black solid powder of the polymer shown as a formula J52-F-D1, wherein the yield is 96 percent;
polymer J52-F-D1 elemental analysis test results: the mass percentage of part of elements in J52-F-D1 obtained by theoretical calculation is as follows: 68.06% for C, 6.93% for H and 17.93% for S. The actual measured results are: 67.98% for C, 6.84% for H and 17.91% for S.
Example 5 solubility and film formation testing of unequal amount of donor-acceptor unit type polymers according to the invention
The polymers PM6-D1, PM6-D2, PM6-D3 and J52-F-D1 prepared in examples 1, 2, 3 and 4 are respectively put in common organic solvents, such as chlorobenzene, dichlorobenzene, chloroform, toluene, trichlorobenzene, methanol and the like. The polymer was found to have good solubility in chlorinated solvents, but was not soluble in methanol. A high-quality film can be prepared by spin coating dichlorobenzene solution of any one of polymers PM6-D1, PM6-D2, PM6-D3 and J52-F-D1 on a glass sheet.
Example 6 measurement of optical band gap thereof by absorption Spectroscopy
The absorption spectra of the polymers PM6-D1, PM6-D2 and PM6-D3 prepared in examples 1, 2 and 3 measured in chloroform solution and film are shown in FIG. 2. The optical bandgap of a polymer can be represented by the empirical formula (E) g ＝1240/λ Absorption edge ) Calculated and shown in table 1. FIG. 6 shows an absorption spectrum of a polymer J52-F-D1 in chloroform, which was produced in example 4 of the present invention.
TABLE 1 optical absorption data for films of polymers PM6-D1, PM6-D2, PM6-D3, J52-F-D1
| Polymer and method of making same | λ max (nm) | λ edge (nm) | E g opt (eV) |
| PM6-D1 | 572 | 667 | 1.86 |
| PM6-D2 | 570 | 677 | 1.83 |
| PM6-D3 | 562 | 663 | 1.87 |
| J52-F-D1 | 626 | 655 | 1.89 |
The maximum absorption of the polymer PM6-D1, PM6-D2, PM6-D3 and J52-F-D1 films prepared in examples 1, 2, 3 and 4 are 572nm, 570nm, 562nm and 626nm respectively, the absorption edges are 667nm, 677nm, 663nm and 655nm respectively, and the corresponding optical band gaps are 1.86eV, 1.83eV, 1.87eV and 1.89eV respectively, so that the polymers PM6-D1, PM6-D2, PM6-D3 and J52-F-D1 are typical intermediate band gap conjugated polymer materials.
Example 7 determination of the electronic energy levels of non-equivalent donor-acceptor unit polymers according to the invention by means of electrochemical cyclic voltammetry.
The polymers PM6-D1, PM6-D2 and PM6-D3(0.5mg) prepared in example 1, example 2 and example 3 were dissolved in 1mL of chloroform, and then the solution was added dropwise to a working electrode such as a platinum plate; taking 0.1mol/L acetonitrile solution of tetrabutylammonium hexafluorophosphate as electrolyte; taking a platinum wire as a counter electrode; the Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) of the polymer were determined with silver wire/silver chloride as reference electrode. The same procedure was repeated to determine the HOMO, LUMO energy levels of other polymers in the examples of the invention. The cyclic voltammograms of the polymers PM6-D1, PM6-D2, PM6-D3 prepared in examples 1, 2, 3 of the invention are shown in FIG. 3. The HOMO of the polymers PM6-D1, PM6-D2 and PM6-D3 prepared in the embodiments 1, 2 and 3 of the invention are respectively-5.51 eV, -5.53eV and-5.56 eV, and the LUMO is respectively-3.60 eV, -3.59eV and-3.56 eV. The polymers PM6-D1, PM6-D2 and PM6-D3 prepared in the examples 1, 2 and 3 of the invention have appropriate molecular energy levels, so that the application of the polymers in polymer solar cells is ensured.
Example 8 preparation of Polymer solar cell devices of conventional construction the non-equivalent donor-acceptor unit class polymers of the present invention were tested for their photovoltaic performance
The polymers PM6-D1, PM6-D2 and PM6-D3 prepared in examples 1, 2 and 3 of the invention are respectively blended and dissolved in dichlorobenzene to prepare 18mg/mL blended active layer solution according to the weight ratio of 1:1.5 with a non-fullerene acceptor Y6 (the molecular structure is shown in figure 1). After the solution is fully dissolved, chloronaphthalene with the volume ratio of 0.5 percent is added, the solution is coated on ITO conductive glass containing a PEDOT and PSS interface by spin coating, the annealing is carried out for 10 minutes at the temperature of 90 ℃, and then 30 microliter of PNDIT-F3N solution is thrown; after preparing the sample, the sample is conveyed to an evaporation chamber and plated with 100 nm silver. AAA grade solar simulator AM1.5G (100 mW/cm) was used in a glove box under nitrogen atmosphere 2 ) The open-circuit voltage, the short-circuit current, the fill factor and the energy conversion efficiency of the prepared polymer solar cell device are tested under the intensity of the voltage.
The current density-voltage curve after the test is shown in fig. 4. The open-circuit voltage of the polymer solar cell device corresponding to the polymer PM6-D1 is 0.85V, and the short-circuit current is 26.47mA/cm 2 The fill factor was 78.7% and the energy conversion efficiency was 17.71%. The open-circuit voltage of the polymer solar cell device corresponding to the polymer PM6-D2 is 0.85V, and the short-circuit current is 26.18mA/cm 2 The fill factor was 75.6% and the energy conversion efficiency was 16.82%. The open-circuit voltage of the polymer solar cell device corresponding to the polymer PM6-D3 is 0.86V, and the short-circuit current is 26.01mA/cm 2 The fill factor was 76.1% and the energy conversion efficiency was 17.02%. As shown in table 2:
TABLE 2 Polymer solar cell devices based on PM6-D1: Y6, PM6-D2: Y6, and PM6-D3: Y6 at AM1.5G,100mW/cm 2 Photovoltaic performance parameters under light conditions
Example 9
The external quantum efficiency measured by the optimized device in this example 8 is shown in fig. 5, and the current obtained by integrating the external quantum efficiency is 25.66m with m cm based on devices of PM6-D1: Y6, PM6-D2: Y6, PM6-D3: Y6 -2 ,25.51mAcm -2 ，25.26mA cm -2 。
Claims (10)
1. A non-equivalent amount of donor-acceptor unit D-A copolymer having the formula I:
in formula I, D represents a donor unit group and is selected from one of the following structural formulas:
in the formula II-1 and the formula II-2, R is selected from any one of the following groups: alkyl, alkoxy, alkylthio, silyl and ester groups, wherein the alkyl contained in each group is a linear or branched alkyl group having 1 to 12 carbon atoms;
in formula I, A represents an acceptor unit group selected from any one of the following structural formulas:
in the formulas III-1 and III-2, R is selected from any one of the following groups: alkyl, alkoxy, alkylthio, silyl and ester groups, wherein the alkyl contained in each group is a linear or branched alkyl group having 1 to 12 carbon atoms;
in the formula I, x takes a value of 0.1-0.75;
n is a natural number between 5 and 100.
2. The unequal donor-acceptor unit D-a copolymer according to claim 1, wherein: the unequal donor-acceptor unit D-A copolymer has the following structure:
3. a process for preparing a non-equivalent donor-acceptor unit D-a copolymer according to claim 1 or 2 comprising the steps of:
a one-pot method: in the presence of a catalyst, reacting 1 equivalent of compound 1, x equivalent of compound 2 and (1-x) equivalent of compound 3 to obtain an unequal amount of donor-acceptor unit D-A copolymer shown in formula I;
wherein x is 0.1-0.75;
in the compounds 1 and 2, the group represented by D is the same as the group represented by D in the copolymer of formula I in claim 1;
in the compound 3, the group represented by A is the same as the group represented by A in the copolymer of formula I in claim 1.
4. The method of claim 3, wherein: the catalyst is palladium tetratriphenylphosphine;
the proportion of the catalyst to the compound 1 is as follows: 20-80 mg: 1mmol of the active component;
the reaction is carried out in an organic solvent, wherein the organic solvent is at least one of toluene, chlorobenzene, o-xylene and o-dichlorobenzene;
the reaction is carried out under the protection of inert gas, and the inert gas can be at least one of argon and nitrogen;
the reaction conditions are as follows: heating and refluxing for 12-48 h.
5. Use of a non-equivalent amount of a donor-acceptor unit D-A copolymer as defined in claim 1 or 2 as donor material in the preparation of a photoactive layer.
6. A photoactive layer comprising a copolymer of unequal donor-acceptor units D-A as defined in claim 1 or 2 and an n-type electron acceptor,
wherein the weight ratio of the n-type electron acceptor to the unequal donor-acceptor unit D-A copolymer is 1: 0.5-2.
7. A process for preparing the photoactive layer of claim 6, comprising: a process for preparing a copolymer of D-A type as defined in claim 1 or 2, which comprises mixing a non-equivalent amount of the donor-acceptor unit with an n-type electron acceptor in a solvent and coating the mixture.
8. The method of claim 7, wherein: the solvent is selected from: at least one of toluene, xylene, trimethylbenzene, chloroform, chlorobenzene, dichlorobenzene, and trichlorobenzene;
in the resulting mixture, the concentration of the non-equivalent amount of the D-A copolymer as donor-acceptor units is from 0.5mg/mL to 50mg/mL,
the concentration of the n-type electron acceptor is 0.5 mg/mL-50 mg/mL.
9. Use of a non-equivalent donor-acceptor unit D-A copolymer as defined in claim 1 or 2 or a photoactive layer prepared from a non-equivalent donor-acceptor unit D-A copolymer as defined in claim 1 or 2 in the preparation of a functional energy device as defined below: a thin film semiconductor device, a light detecting device, a polymer solar cell device, or a photoelectric device.
10. A polymer solar cell device, comprising: a bottom electrode, a top electrode, and at least one organic semiconducting photovoltaically active layer disposed between the two electrodes, the photovoltaically active layer comprising a non-equivalent D-A copolymer of donor-acceptor units as defined in claim 1 or 2 and an organic semiconducting acceptor.
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