CN115746016A - Donor compound containing multiple side chain substitution and method, polymer material and method, membrane material, assembly, battery and device - Google Patents
Donor compound containing multiple side chain substitution and method, polymer material and method, membrane material, assembly, battery and device Download PDFInfo
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 29
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- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical class C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 claims description 21
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention discloses a donor compound containing multi-side chain substitution and a method thereof, a polymer material and a method thereof, a membrane material, a component, a battery and a device, wherein the donor compound has the following structural general formula:
the invention makes it possible to obtain donor materials by optimal coordination with different electron-withdrawing units and to obtain polymeric donor materials which have good solution processability and are obtained from materialsThe photoelectric property, the aggregation behavior, the molecular orientation, the film morphology, the charge transmission capability and the like are easy to regulate and control.
Description
Technical Field
The present invention relates to organic solar energy technology, and is especially one kind of donor compound containing multiple side chain substitution and its preparation process, polymer material and its preparation process, film material, module, cell and device.
Background
As a new clean energy technology, polymer solar energy conversion devices such as organic solar cells have the advantages of light weight, flexibility, low-temperature solution processing and the like, and are widely concerned by academia and industry. The active layer prepared by blending a polymer donor material and a small molecule acceptor material is a core part of the polymer solar cell. The donor and acceptor materials in the active layer assume important roles of exciton generation, exciton dissociation, charge transport, etc. In recent years, with continuous development and optimization of high-performance polymer donor and small molecule acceptor materials, the photoelectric conversion efficiency of the organic solar cell has made breakthrough progress. Based on the polymer donor: the photoelectric conversion efficiency of the polymer solar cell obtained by blending the small molecule acceptor material has broken through 19% (adv. Mater.2021,33,2102420). However, currently high efficiency devices (more than 16%) are mostly based on a few wide bandgap polymers like PM6, D18 as donor materials. The lack of high performance polymer donor materials has limited the further development of organic solar cells. Therefore, the development of a novel high-efficiency polymer donor material has great significance for further improving the photoelectric conversion efficiency of the polymer solar cell.
The information disclosed in this background section is only for enhancement of understanding of the general background of the invention and should not be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person skilled in the art.
Disclosure of Invention
The invention aims to provide a donor compound containing multi-side chain substitution, a method, a polymer material, a method, a membrane material, a component, a battery and a device, wherein the obtained compound can be copolymerized with different electron-withdrawing units according to product requirements to obtain a series of high-performance polymer donor materials. On one hand, the photoelectric property, the aggregation behavior, the molecular orientation, the film morphology and the final device performance of the target polymer donor material can be effectively modulated through the changes of the carbon chain length, the branching position, the substitution position, the functional group type, the conjugation length and the like on the side chain. On the other hand, functional groups such as halogen, cyano and the like are introduced to the side chain of the electron donor unit, intramolecular non-covalent interaction is hopeful to be formed, and further regulation and control of molecular planarity are achieved, so that the charge transfer characteristic of the target polymer donor is changed, and the purpose of optimizing device performance is finally achieved. Thus, a series of p-type polymer donor materials are obtained by copolymerizing different electron-withdrawing units by using electron-donating units containing multi-side chain substitution as building blocks. The polymer donor material has good solution processing performance, and the photoelectric performance, aggregation behavior, molecular orientation, film morphology, charge transmission capability and the like of the material are easy to regulate and control.
In order to achieve the above objects, embodiments of the present invention provide donor compounds containing multiple side chain substitutions, which are applied to organic solar materials, and have the following structural formula:
wherein R is 1 、R 2 、R 3 Is independently selected from hydrogen atom, halogen atom, C1-C28 alkyl, C1-C28 fluorinated alkyl, C1-C28 partially fluorinated alkyl, C1-C20 alkoxy, C1-C20 alkylthio, cyano, ester group, carbonyl;
x is O, S, se;
a is selected from
In one or more embodiments of the present invention, a process for preparing a donor compound containing multiple pendant substitutions comprises the steps of:
A. the preparation of the intermediate I based on benzene ring substituted benzodithiophene bromination comprises the following steps: bromine substitution is carried out on a raw material I, wherein the raw material I is
R 1 Selected from the group consisting of: C1-C28 alkyl, C1-C28 alkoxy, C1-C28 alkylthio, C1-C28 fluorinated alkyl;
B. the preparation of the intermediate II based on alpha-position substitution of thiophene in benzodithiophene is as follows: in PddppfCl 2 Under the catalysis of the thiophene zinc reagent, the thiophene zinc reagent and the intermediate I carry out substitution reaction at alpha position;
C. the preparation of intermediate III based on the beta-substitution of thiophene in benzodithiophene is as follows: under the catalysis of Pd (PPh 3) 4, a side chain substituted five-membered heterocyclic tin reagent and an intermediate II are subjected to substitution reaction at a beta position, wherein the side chain substituted five-membered heterocyclic tin reagent is
R2, R3 are independently selected from: a hydrogen atom, a halogen atom, a C1-C28 alkyl group, a C1-C28 fluorinated alkyl group, a C1-C28 partially fluorinated alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a cyano group, an ester group, a carbonyl group;
D. preparing a monomer: and (3) carrying out bromination reaction on the alpha position of the thiophene bridge connected with the benzodithiophene of the intermediate III under the action of NBS to obtain the electron donor unit containing multi-side chain substitution.
In one or more embodiments of the present invention, the D-A type polymer donor material containing multiple side chain substitution is applied to an organic solar material, and the structural formula of the material is as follows:
In one or more embodiments of the present invention, a method for preparing a D-A type polymer donor material containing multiple pendant substitutions comprises the steps of:
A. the preparation of the intermediate I based on benzene ring substituted benzodithiophene bromination comprises the following steps: bromine substitution of a starting material I, wherein the starting material I is
R 1 Selected from the group consisting of: C1-C28 alkyl, C1-C28 alkoxy, C1-C28 alkylthio, C1-C28 fluorinated alkyl;
B. based on benzodithianesThe preparation of the intermediate II substituted by thiophene alpha position in the thiophene is as follows: in PddppfCl 2 Under the catalysis of the thiophene zinc reagent, the thiophene zinc reagent and the intermediate I carry out substitution reaction at alpha position;
C. the preparation of intermediate III based on the beta-substitution of thiophene in benzodithiophene is as follows: under the catalysis of Pd (PPh 3) 4, a side chain substituted five-membered heterocyclic tin reagent and an intermediate II are subjected to substitution reaction at a beta position, wherein the side chain substituted five-membered heterocyclic tin reagent is
R 2 、R 3 Independently selected from: a hydrogen atom, a halogen atom, a C1-C28 alkyl group, a C1-C28 fluorinated alkyl group, a C1-C28 partially fluorinated alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a cyano group, an ester group, a carbonyl group;
D. preparing a monomer: under the action of NBS, the intermediate III is subjected to bromination reaction at the alpha position of a thiophene bridge connected with benzodithiophene to obtain a dibrominated electron donor unit containing multi-side-chain substitution;
E. synthesis of the polymer donor material: stille polymerization of monomers with monomers containing bistrimethylstannyl or bistributylstannyl groups.
In one or more embodiments of the invention, the film material, at least, includes several donor sheets formed primarily from D-A type polymer donor materials containing multiple pendant substitution as previously described.
In one or more embodiments of the present invention, the film material further includes a substrate, and the donor film is formed at least on a surface of the substrate.
In one or more embodiments of the invention, a solar module comprises a light energy conversion structure comprising a body and a film material as described above carried on the body.
In one or more embodiments of the invention, a solar cell comprises at least a solar module as described above and an electrically conductive structure electrically connected to the film material.
In one or more embodiments of the present invention, the solar energy device at least comprises an energy storage and transportation device and the solar module as described above and/or the solar cell as described above, and the energy storage and transportation device is used for storing and transferring the energy generated by the solar module as described above or storing and transferring the electric energy generated by the solar cell as described above.
In one or more embodiments of the invention, the energy is selected from the group consisting of electrical energy, thermal energy, optical energy, microwave energy, mechanical energy.
In the scheme of the invention, by utilizing the specific donor compound and the polymer material prepared by the donor compound, the advantages of production, processing and molding are integrated, and meanwhile, the high-efficiency conversion of solar energy, namely clean energy, can be realized, so that the convenience and flexibility of solar energy utilization are realized, and the industrialization is promoted. For example, solar energy can be converted into electric energy, thermal energy, etc. according to the specific and application requirements of the construction site, specifically storage, transportation and delivery, and application requirements. The components, devices, etc. of the present invention may be adapted to other existing functional components. For example, when the solar energy power generation is used, an inverter, a transformer, etc. are required to be matched, and nothing that is irrelevant to the innovation of the present invention is not additionally limited herein.
Compared with the prior art, the donor compound containing multi-side chain substitution and the method thereof, the polymer material and the method thereof, the membrane material, the component, the battery and the device,
the electron-donating unit containing the multi-side-chain substituted polymer donor material is a structure with a plane rigid conjugated skeleton, and the unit is introduced into a polymer main chain to promote the close packing among polymer molecular chains, so that the material is endowed with excellent hole transport performance; meanwhile, the donor unit contains multi-side chain substitution, and the synthesized polymer has good solubility and can meet the requirement of solution processing; in addition, the photoelectric property, the aggregation behavior, the molecular orientation, the intermolecular interaction strength and the like of the target polymer donor material can be effectively modulated by regulating the carbon chain length, the branching position, the substitution position, the functional group type, the conjugation length and the like of the side chain; finally, active layers based on such polymer donors can form appropriate phase separation, facilitating efficient dissociation of excitons.
Drawings
FIG. 1 is a drawing of Compound 2 according to one embodiment of the present invention 1 HNMR spectrogram;
FIG. 2 is a drawing of Compound 4 according to one embodiment of the present invention 1 HNMR spectrogram;
FIG. 3 is a drawing of Compound 5 according to one embodiment of the present invention 1 HNMR spectrogram;
FIG. 4 shows a block diagram of a polymer PL4 according to an embodiment of the present invention 1 HNMR spectrogram;
FIG. 5 shows a polymer PL5 according to an embodiment of the present invention 1 HNMR spectrogram;
FIG. 6 is a drawing of Compound 11 according to one embodiment of the present invention 1 HNMR spectrogram;
FIG. 7 is a drawing of Compound 12 according to one embodiment of the present invention 1 HNMR spectrogram.
Detailed Description
Specific embodiments of the present invention will be described in detail below with reference to the accompanying drawings, but it should be understood that the scope of the present invention is not limited to the specific embodiments.
Throughout the specification and claims, unless explicitly stated otherwise, the word "comprise", or variations such as "comprises" or "comprising", will be understood to imply the inclusion of a stated element or component but not the exclusion of any other element or component.
In the scheme of the invention, the donor compound containing the multi-side chain substitution is prepared by adopting the following method, and the donor compound is a D-A type polymer donor material containing the multi-side chain substitution:
1. preparation of benzodithiophene brominated intermediates based on benzene ring substitution
Benzo-dithiophene-based brominated intermediates, R herein, can be prepared according to literature procedures (Natl. Sci. Rev.,2020,7,1886-1895) 1 Can be independently selected from C1-C28 alkyl and C1-C28 alkoxyAlkylthio of C1-C28, fluorinated alkyl of C1-C28.
2. Preparation of intermediates based on alpha-substitution of thiophenes in benzodithiophenes
Can be in PdppfCl 2 Under the catalysis of (3), the thiophene zinc reagent reacts with the brominated intermediate of the benzodithiophene, and the reaction site is on the thiophene alpha position of the benzodithiophene.
3. Preparation of intermediates based on the beta-substitution of thiophenes in benzodithiophenes
Can be in Pd (PPh) 3 ) 4 Under the catalysis of (1), a five-membered heterocyclic tin reagent containing side chain substitution reacts with bromine on the beta position of thiophene of benzodithiophene, wherein X can be O, S, se. R in this case 2 、R 3 May be independently selected from a hydrogen atom, a halogen atom, a C1-C28 alkyl group, a C1-C28 fluorinated alkyl group, a C1-C28 partially fluorinated alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a cyano group, an ester group, a carbonyl group;
4. preparation of polymeric monomers containing multiple pendant substitutions
Under the action of NBS, the alpha site of a thiophene bridge connected with benzodithiophene is subjected to bromination reaction to obtain an electron donor unit containing multi-side chain substitution.
On the basis of this, it is also possible to further polymerize (step 5), thus obtaining a polymer donor material (i.e. a polymeric material obtained by polymerization of the above-mentioned monomers):
5. synthesis of polymeric donor materials
The dibrominated monomers containing multiply pendant substituted electron donor units can be Stille polymerized with monomers containing bistrimethylstannyl or bistrimethylstannyl groups.
The advantages of the embodiment of the present invention will be illustrated by the preparation and application of two polymers of the embodiment of the present invention, but it should be understood that the description is not intended to limit the scope of the embodiment of the present invention.
Under an inert atmosphere, sequentially adding 2-bromothiophene (0.75g, 4.57mmol) and 15mL of anhydrous ether into a 50mL double-neck flask, and bubbling nitrogen gas into the solution for 5 minutes; subsequently, the system was cooled to-78 deg.C, and n-butyllithium solution (2.1mL, 5.03mmol) was slowly injected, the temperature was maintained for 1 hour, and then ZnCl was injected into the bottle 2 Slowly heating the solution (5.1mL, 5.03mmol) to 0 ℃, and continuously preserving the temperature for 1 hour; finally, compound 1 (0.5g, 0.57mmol) (synthesized according to the method reported by Natl.Sci.Rev.,2020,7,1886-1895) was reacted with the catalyst PddppfCl 2 (0.042g, 0.057 mmol) is added into a reaction bottle, the temperature is raised to reflux, and the reaction is carried out for 12 hours; after the reaction was completed, the reaction was quenched with saturated aqueous ammonium chloride solution, the organic layer was extracted with ether, the organic layers were combined, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography (petroleum ether as eluent) to obtain a yellow solid (0.37g, 73%). 1 H NMR(400MHz,CDCl 3 ):δ7.68-7.63(m,2H),7.55–7.49(m,2H),7.21–7.17(m,2H),4.10(d,J＝6.4Hz,4H),1.68-1.63(m,2H),1.55–1.24(m,32H),1.00–0.89(m,12H).
Synthesis of Compound 4: a dry 25mL two-necked flask was taken, and to this flask was added sequentially compound 3 (0.57g, 1.36mmol) (synthesized according to the method reported in J.Mater. Chem.C., 2016,4,3809-3814), compound2 (0.3 g, 0.34mmol) and 10mL of toluene, the solution was purged with nitrogen for 15 minutes, and then the catalyst Pd (PPh) was added to the bottle 3 ) 4 (0.04g, 0.034mmol), continued to be purged with nitrogen for 5 minutes, heated to reflux, and reacted for 12 hours. After the reaction was completed, the crude product was extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and further purified by column chromatography (dichloromethane: petroleum ether =1, 30 as an eluent) to obtain a yellow solid (0.41g, 98%). 1 H NMR(400MHz,CDCl 3 ):δ7.25-7.20(m,4H),6.99–6.94(m,4H),6.81(d,J＝3.6Hz,2H),3.67(d,J＝6.3Hz,4H),2.84(d,J＝6.6Hz,4H),1.75-1.66(m,2H),1.44–1.17(m,66H),0.99–0.87(m,24H).
Synthesis of Compound 5: a dry 25mL single neck round bottom flask was taken, and Compound 4 (0.1g, 0.082mmol) and 10mL tetrahydrofuran were added to the flask in this order, the solution was purged with nitrogen for 15 minutes, and then the flask was treated with light and N-bromosuccinimide (0.1g, 0.56mmol) was added thereto, and reacted at room temperature for 12 hours. After the reaction was completed, it was quenched with saturated aqueous sodium sulfite solution, extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain a yellow oil, which was then isolated and purified by column chromatography (dichloromethane: petroleum ether =1:50 as an eluent) to obtain a yellow solid (0.08g, 71%). 1 H NMR(400MHz,CDCl 3 ):δ7.02(m,2H),6.96(m,2H),6.93(m,2H),6.83(d,J＝3.1Hz,2H),3.66(d,J＝5.82Hz,4H),2.87(d,J＝6.5Hz,4H),1.78-1.66(m,2H),1.56–1.07(m,66H)1.04–0.76(m,24H).
Synthesis of Polymer PL4: taking a dry 25mL double-neck flask, and adding into the flask in sequence for meltingCompound 6 (0.063g, 0.0724mmol) and 9mL toluene were sparged with nitrogen for 15 minutes, and then compound 5 (0.1g, 0.0724mmol), the catalyst Pd, was added to the bottle 2 (dba) 3 (0.003g, 0.004mmol) and ligand P (o-tol) 3 (0.002g, 0.08mmol), nitrogen sparge was continued for 5 minutes, heated to reflux, and reacted for 78 hours. After the reaction, the crude product was successively extracted with methanol, acetone and n-hexane for 24 hours, then extracted with dichloromethane and chloroform, respectively, concentrated under reduced pressure, dissolved in a small amount of chloroform and precipitated as a solid by adding methanol, and filtered to give a dark red polymer PL4 (0.111g, 76%). M n ＝55.1kDa,PDI＝2.17。
Step 5, preparation of Polymer PL5
Synthesis of PL5: polymer PL5 was synthesized by following the same synthetic route as PL4, the reaction was terminated, and the crude product was successively extracted with methanol, acetone, and n-hexane for 24 hours, then extracted with dichloromethane, concentrated under reduced pressure, dissolved with a small amount of dichloromethane, and added with methanol to precipitate a solid, which was filtered to give a dark red polymer PL5 (yield 71%). M is a group of n ＝64.3kDa,PDI＝2.41。
Compound 8 (0.66g, 3.08mmol) (synthesized according to the method reported in j. Mater. Chem.a,2019,7,2646-2652) and anhydrous tetrahydrofuran (10 mL) were added to a dry 50mL two-necked flask under nitrogen, bubbled with nitrogen for 10 minutes, then cooled to-78 ℃, LDA solution (1.7ml, 3.39mmol) was slowly injected into the flask, and the temperature was held for 1 hour; then, a tetrahydrofuran solution of trimethyltin chloride (0.92g, 4.62mmol) was poured into a bottle, slowly warmed to room temperature overnight, and the resulting crude product was extracted with dichloromethane, dried over anhydrous magnesium sulfate and used directly for the next reaction.
Step 7, preparation of Compound 11
A dry 25mL two-necked flask was taken, and Compound 10 (0.15g, 0.195mmol), compound 9 (0.54g, 1.17mmol) and 10mL of toluene were sequentially charged into the flask, and the solution was purged with nitrogen for 15 minutes, after which the catalyst Pd (PPh) was added to the flask 3 ) 4 (0.03g, 0.02mmol), and nitrogen was bubbled continuously for 5 minutes, and the reaction was heated to reflux for 12 hours. After the reaction is complete, the crude product is extracted with dichloromethane, the organic phase is dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by column chromatography (petroleum ether as eluent) to give a yellow solid (0.17g, 85%). 1 H NMR(400MHz,CDCl 3 ):δ7.32-7.29(m,2H),7.26–7.23(m,2H),7.02–6.98(t,2H),6.88–6.84(s,2H),3.76–3.68(d,J＝4.0Hz,4H),2.79–2.75(d,J＝6.8Hz,4H),1.65–1.62(m,2H),1.34–1.26(m,34H),0.96–0.90(m,24H)。
A dry 25mL single neck round bottom flask was charged with Compound 11 (0.2g, 0.193mmol) and 20mL tetrahydrofuran in that order, purged with nitrogen for 15 minutes, and then the flask was treated with light and N-bromosuccinimide (1.13g, 6.37mmol) was added and reacted at room temperature for 12 hours. After the reaction, the reaction mixture was quenched with saturated aqueous sodium sulfite solution, extracted with dichloromethane, the organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give a yellow oily substance, which was then purified by column chromatography (petroleum ether as eluent) to give a yellow solid (0.18g, 78%). 1 H NMR(400MHz,CDCl 3 ):δ7.04–7.02(d,J＝3.6Hz,2H),6.96–6.93(d,J＝3.6Hz,2H),6.86–6.83(s,2H),3.71–3.66(d,J＝4.4Hz,4H),3.71–3.66(d,J＝4.4Hz,4H),2.79–2.74(d,J＝6.4Hz,4H),1.65-1.61(m,2H),1.49–1.17(m,34H)1.00–0.74(m,24H)。
Step 9, preparation of Polymer PL6
The synthesis route of the polymer PL6 is similar to that of PL4, the reaction is finished, the crude product is sequentially subjected to soxhlet extraction for 24 hours by using methanol, acetone, normal hexane and dichloromethane, then subjected to soxhlet extraction by using trichloromethane, concentrated under reduced pressure, dissolved by using a small amount of trichloromethane, added with methanol to precipitate a solid, and filtered to obtain the dark red polymer PL6 (the yield is 62%).
And (3) preparing a solar cell device by using the D-A type polymer donor material containing the multi-side chain substitution obtained in the steps 4, 5 and 9, and testing.
In the examples including those shown below, the small molecule acceptor material of interest may be Y6 (CAS: 2304444-49-1) having the following structural formula:
it should be noted that the small molecule acceptor material is not limited to the above Y6 compound, and other small molecule acceptor materials, such as another small molecule acceptor material CAS from gazette research science and technology ltd: 2389125-23-7, etc., all of which do not affect the implementation of the scheme of the present invention.
Example 1 device preparation of Polymer donors PL4
The solar cell device adopts a positive device structure:
glass substrate/ITO/PEDOT PSS/photoactive layer/PDIN/Ag. The ITO layer is attached to a glass substrate, the ITO and the glass substrate are called ITO glass for short, and the ITO glass is sequentially washed by detergent, water, acetone and isopropanol for thirty minutes under ultrasound. Then dried in an oven at 90 ℃ overnight. After the ITO glass is treated with ultraviolet ozone for 15 minutes, PEDOT, PSS, is spin-coated on the ITO layer, and is placed in an oven at 140 ℃ for heating for 15 minutes, and then is quickly transferred to a glove box for standby. Coupling small molecule acceptor Y6 and polymer donorMaterial PL4 (PL 4: Y6) was dissolved in chloroform at a weight ratio of 1.4, 1% by volume of 1,8-diiodooctane was added as an additive, the total concentration of the solution was 20mg/mL, the solution was stirred at 50 ℃ for 4 hours, and then the solution was spin-coated as an active layer on a PEDOT: PSS film to a thickness of about 100nm. In order to improve the electron injection efficiency, a methanol solution of PDIN (1.5 mg/mL containing acetic acid at a mass concentration of 0.2%) was spin-coated on the active layer. Finally, the negative electrode of the cell was at a vacuum of about 5X 10 -5 The evaporation of a 100nm silver electrode is finished under the Pa condition, and the area of the device is 5mm 2 。
Example 2 device preparation of Polymer donors PL5
The only difference was that the active layer was PL5: Y6, as in example 1.
Example 3 device preparation of Polymer donors PL6
The only difference was that the active layer was PL6: Y6, as in example 1.
The devices obtained in examples 1 to 3 were subjected to performance tests: the device was tested by simulating AM 1.5G (100 mW/cm) with a solar simulator of the SS-X50 (Enliech) type 2 ) Measured using a Keithley 2400 digital source meter tester under light. The parameters of the solar cell devices obtained in examples 1 to 3 are summarized in Table 1.
TABLE 1 solar cell device parameters prepared based on the donor materials
TABLE 2 hole and Electron mobilities of hybrid films prepared based on the donor materials
The foregoing descriptions of specific exemplary embodiments of the present invention have been presented for purposes of illustration and description. It is not intended to limit the invention to the precise form disclosed, and obviously many modifications and variations are possible in light of the above teaching. The exemplary embodiments were chosen and described in order to explain certain principles of the invention and its practical application to enable one skilled in the art to make and use various exemplary embodiments of the invention and various alternatives and modifications as are suited to the particular use contemplated. It is intended that the scope of the invention be defined by the claims and their equivalents.
Claims (10)
1. A donor compound containing multi-side chain substitution is applied to organic solar materials and has the following structural general formula:
wherein R is 1 、R 2 、R 3 Are each independently selected from: a hydrogen atom, a halogen atom, a C1-C28 alkyl group, a C1-C28 fluorinated alkyl group, a C1-C28 partially fluorinated alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a cyano group, an ester group, a carbonyl group;
x is O, S, se;
a is selected from
2. A process for the preparation of a donor compound containing a multiple side-chain substitution according to claim 1, comprising the steps of:
A. the preparation of the intermediate I based on benzene ring substituted benzodithiophene bromination comprises the following steps: bromine substitution of a starting material I, wherein the starting material I is
R 1 Selected from: C1-C28 alkyl, C1-C28 alkoxy, C1-C28 alkylthio, C1-C28 fluorinated alkyl;
B. the preparation of the intermediate II based on alpha-position substitution of thiophene in benzodithiophene is as follows: in PddppfCl 2 Under the catalysis of the thiophene zinc reagent, the thiophene zinc reagent and the intermediate I carry out substitution reaction at alpha position;
C. the preparation of intermediate III based on the beta-substitution of thiophene in benzodithiophene is as follows: under the catalysis of Pd (PPh 3) 4, a side chain substituted five-membered heterocyclic tin reagent and an intermediate II are subjected to substitution reaction at a beta position, wherein the side chain substituted five-membered heterocyclic tin reagent is
R 2 、R 3 Independently selected from: a hydrogen atom, a halogen atom, a C1-C28 alkyl group, a C1-C28 fluorinated alkyl group, a C1-C28 partially fluorinated alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a cyano group, an ester group, a carbonyl group;
D. monomer preparation: and (3) carrying out bromination reaction on the alpha position of the thiophene bridge connected with the benzodithiophene of the intermediate III under the action of NBS to obtain the electron donor unit containing multi-side chain substitution.
3. A D-A type polymer donor material containing multi-side chain substitution is applied to an organic solar material and has the following structural general formula:
obtained by polymerizing a donor compound containing a multiple side-chain substitution according to claim 1, wherein n is a positive integer from 10 to 1000.
4. A process for the preparation of a polymeric donor material of the type D-a containing multiple side chain substitutions according to claim 3, comprising the following steps:
A. the preparation of the intermediate I based on benzene ring substituted benzodithiophene bromination comprises the following steps: bromine substitution of a starting material I, wherein the starting material I is
R 1 Selected from: C1-C28 alkyl, C1-C28 alkoxy, C1-C28 alkylthio, C1-C28 fluorinated alkyl;
B. the preparation of the intermediate II based on alpha-position substitution of thiophene in benzodithiophene is as follows: in PddppfCl 2 Under the catalysis of the thiophene zinc reagent, the thiophene zinc reagent and the intermediate I carry out substitution reaction at alpha position;
C. the preparation of intermediate III based on the beta-substitution of thiophene in benzodithiophene is as follows: under the catalysis of Pd (PPh 3) 4, a side chain substituted five-membered heterocyclic tin reagent and an intermediate II are subjected to substitution reaction at a beta position, wherein the side chain substituted five-membered heterocyclic tin reagent is
R 2 、R 3 Independently selected from: a hydrogen atom, a halogen atom, a C1-C28 alkyl group, a C1-C28 fluorinated alkyl group, a C1-C28 partially fluorinated alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a cyano group, an ester group, a carbonyl group;
D. monomer preparation: under the action of NBS, the intermediate III is subjected to bromination reaction at the alpha position of a thiophene bridge connected with benzodithiophene to obtain a dibrominated electron donor unit containing multi-side-chain substitution;
E. synthesis of polymer donor material: stille polymerization of the monomers with monomers containing bistrimethylstannyl or bistrimethylstannyl groups.
5. A film material comprising at least several donor sheets formed mainly of a polymeric donor material of the type D-a containing multiple side chain substitutions according to claim 3.
6. The film material of claim 5, further comprising a substrate, wherein the donor film is formed on at least a surface of the substrate.
7. A solar module comprising a light energy conversion structure comprising a body and the film material of claim 5 or 6 carried on the body.
8. Solar cell comprising at least a solar module according to claim 7 and an electrically conductive structure electrically connected to the film material.
9. Solar installation comprising at least an energy storage and transportation device for storing energy generated by transferring a solar module according to claim 7 or for storing electrical energy generated by transferring a solar cell according to claim 8, and a solar module according to claim 7 and/or a solar cell according to claim 8.
10. The solar device of claim 9, wherein the energy is selected from the group consisting of electrical energy, thermal energy, optical energy, microwave energy, and mechanical energy.
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