CN117820610A - Single-component block polymer photovoltaic material based on polythiophene donor, and preparation method and application thereof - Google Patents
Single-component block polymer photovoltaic material based on polythiophene donor, and preparation method and application thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 50
- 229920000123 polythiophene Polymers 0.000 title claims abstract description 13
- 238000013087 polymer photovoltaic Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 29
- 239000012634 fragment Substances 0.000 claims abstract description 18
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- -1 5, 5-dibromo- [2,2] -bithiophene-4, 4-dicarboxylic acid bis (2-butyl octyl) ester Chemical compound 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- KKRPPVXJVZKJON-UHFFFAOYSA-N trimethyl-(5-trimethylstannylthiophen-2-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=C([Sn](C)(C)C)S1 KKRPPVXJVZKJON-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 239000002861 polymer material Substances 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- DOIRPCDOGSNNCS-UHFFFAOYSA-N trimethyl-[5-(5-trimethylstannylthiophen-2-yl)thiophen-2-yl]stannane Chemical compound S1C([Sn](C)(C)C)=CC=C1C1=CC=C([Sn](C)(C)C)S1 DOIRPCDOGSNNCS-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 2
- 238000010494 dissociation reaction Methods 0.000 abstract description 3
- 230000005593 dissociations Effects 0.000 abstract description 3
- 238000012545 processing Methods 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- 238000012986 modification Methods 0.000 description 8
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- 238000010521 absorption reaction Methods 0.000 description 6
- 238000005424 photoluminescence Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000013086 organic photovoltaic Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910003472 fullerene Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000012938 design process Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000006355 external stress Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
Classifications
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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
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Abstract
A single-component block polymer photovoltaic material based on a polythiophene donor, a preparation method and application thereof, wherein the material has the following molecular structure and derivatives thereof:the preparation method comprises the following steps: synthesizing a PDCBT fragment of the polymer donor material; synthesis of a PYIT fragment of the polymer acceptor material; donor polymer monocomponent material PDCBT-b-synthesis of PYIT. The material can be used as a photoactive layer material and applied to the preparation of single-component organic solar devices. The invention can realize effective exciton dissociation and charge generation; the processing is simpler and more convenient; the stability of the device is better;simple structure and low synthesis cost.
Description
Technical Field
The invention relates to the field of single-component organic solar cells, in particular to application of a single-component block polymer material based on a polythiophene donor and a Y-series receptor in synthesizing an organic solar cell device.
Background
Organic Photovoltaics (OPVs) are an emerging technology that has the feasibility of large-scale roll-to-roll manufacturing, and has the advantages of light weight, high flexibility, low cost, and the like. With the rapid development of advanced semiconductor technology, particularly the advent of a series of non-fullerene receptors (NFAs), the efficiency gap between solar photovoltaic cells and commercial inorganic photovoltaic cells was reduced. The most advanced OPVs are based primarily on Bulk Heterojunction (BHJ) structures, often requiring complex processes to optimize ink preparation and improve topography. Mixing the electron donor and electron acceptor thin film composites kinetically typically results in an unbalanced microstructure, which is typically thermodynamically unstable. Thus, detrimental microstructural phase separation or diffusion of donor/acceptor components may occur under external stress (e.g., temperature or light), resulting in associated performance losses due to microstructural changes. BHJ Organic Solar Cells (OSCs) may suffer from severe morphological degradation, whether rapid ablative decay may occur at the beginning of continuous decay or throughout operation.
To solve the above-mentioned difficulties in industrial applications, the use of single-component materials (SCMs) is an effective method that contains chemically linked donor (D) and acceptor (a) groups in one material and can realize photoelectric conversion by itself. This feature simplifies the ink design process and recovery by involving only one material. Most importantly, the covalent bond structure can fix the interval between the donor and the acceptor, overcomes the condition that the miscibility of some donor and acceptor systems is poor or too good, forms a proper phase separation form, simultaneously inhibits the gradual unmixed between the donor and the acceptor, and provides a long-term stable nano-phase form. It is widely recognized that the use of SCMs is an effective and versatile method to achieve higher stability than the corresponding BHJ.
Disclosure of Invention
Aiming at the problems that the miscibility of the current polythiophene donor and Y-series non-fullerene receptor is too good, the separation scale of an active layer donor-acceptor is too small, so that the device performance is extremely low, the invention provides a single-component block polymer photovoltaic material based on the polythiophene donor, a preparation method and application of the single-component block polymer photovoltaic material in an organic solar cell.
The invention is realized by the following technical scheme.
The molecular structure of the single-component block polymer photovoltaic material based on the polythiophene donor is as follows:
the invention relates to a single-component block polymer photovoltaic material based on a polythiophene donor, which comprises the molecular structure and derivatives thereof.
The invention discloses a preparation method of a single-component block polymer photovoltaic material based on a polythiophene donor, which comprises the following steps of.
(1) Synthesis of the polymeric donor material PDCBT fragment: the raw materials of 5,5 '-bis (trimethylstannyl) -2,2' -bithiophene and 5, 5-dibromo- [2,2] -bithiophene-4, 4-dicarboxylic acid bis (2-butyl octyl) ester are polymerized in solvent toluene to obtain polymer donor PDCBT fragments.
(2) Synthesis of polymer acceptor material PYIT fragment: the raw materials of 2, 5-bis (trimethylstannyl) thiophene and Y5-2Br are polymerized in toluene solvent to obtain a polymer acceptor PYIT fragment.
(3) Donor polymer monocomponent material PDCBT-bSynthesis of PYIT: transferring the polymer donor material PDCBT fragment obtained in the step (1) into a reaction tube of the polymer acceptor material PYIT fragment obtained in the step (2) by using a syringe, and continuing to polymerize to initially obtain a donor polymer monocomponent material PDCBT-bPYIT. Precipitating with methanol, suction filtering, sequentially extracting with n-hexane, acetone, dichloromethane and chloroform, and thenAnd (3) passing through a silica gel chromatographic column, concentrating, settling and suction filtering to obtain the final product of the donor polymer monocomponent material PDCBT-b-PYIT.
The application of the invention is as follows: and (3) taking the synthesized single-component block polymer photovoltaic material based on the polythiophene donor as a photoactive layer material to prepare a single-component organic solar device, so that the high-efficiency photoelectric conversion of the device is realized.
Further, the polymer single-component organic solar cell device comprises an Indium Tin Oxide (ITO) conductive glass anode, an anode modification layer, a photoactive layer, a cathode modification layer and a cathode. Wherein the anode modification layer is PEDOT/PSS (30 nm); the cathode modification layer is PDINN (30 nm); the cathode is a deposition layer of Ag (100 nm); the active layer material is a donor polymer single component material according to the invention.
Compared with the currently reported materials, the donor polymer single-component material has the following characteristics: (1) The polymer donor material and the polymer acceptor material with poor mixed morphology are connected through covalent bonds, so that effective exciton dissociation and charge generation are realized; (2) Covalent attachment of acceptor moieties to a material allows for easier processing of organic solar devices; (3) Because the receptor is connected by covalent bond, the active layer morphology in the aging process of the device can be better resisted, and the stability of the device is better; and (4) the donor part has simple structure and low synthesis cost. Thus, such materials are a very promising class of polymeric monocomponent materials with potential for development and application.
Drawings
FIG. 1 is an ultraviolet-visible absorption spectrum of a PDCBT: PYIT (1:1.1) solid film.
FIG. 2 shows the PDCBT according to the inventionb-uv-vis absorption spectrum of PYIT solid film.
FIG. 3 shows the PDCBT of the inventionbCyclic voltammogram of PYIT solid film.
Fig. 4 is a structural view of an organic solar cell device.
FIG. 5 is a schematic diagram of a PDCBT: PYIT (1:1.1) binary solar cell deviceJ-VA curve.
FIG. 6 shows a PDCBT according to the inventionbPYIT single component solar cell deviceJ-VCurve。
Fig. 7 is a steady state Photoluminescence (PL) spectrum of the PDCBT solid film.
FIG. 8 shows a PDCBT-PYIT (1:1.1) and a PDCBT-according to the inventionb-solid film steady state Photoluminescence (PL) profile of a PYIT control.
Detailed Description
The invention is further illustrated by the following specific examples, which are not intended to limit the scope of the invention in any way.
Example 1
The synthesis route of the donor monocomponent is as follows:
1.1 Synthesis of the polymer acceptor fragment:
y5-2Br (50 mg,0.0267 mmol), 2, 5-bis (trimethylstannyl) thiophene (11 mg,0.0636 mmol), tris (dibenzylideneacetone dipalladium (0.49 mg, 0.000534 mmol), tris (o-methylphenyl) phosphorus (0.65 g,0.002136 mmol), toluene (2 mL) were added in sequence to a 25 ml reaction tube, and the mixture was stirred under reflux in an oil bath at 110℃under nitrogen protection for 5 h.
1.2 Synthesis of polymer donor fragments:
to a 10 ml reaction tube, bis (2-butyloctyl) 5, 5-dibromo- [2,2] -dithiophene-4, 4-dicarboxylic acid (31.3 mg,0.0636 mmol), 5 '-bis (trimethylstannyl) -2,2' -dithiophene (47.6 mg,0.0636 mmol), dipalladium trisdibenzylideneacetone (1.75 mg,0.00191 mmol), tris (o-methylphenyl) phosphorus (2.32 g,0.00764 mmol), toluene (3 mL) were added in this order, and the mixture was stirred and refluxed in an oil bath at 110℃under nitrogen protection to react 3 h.
1.3 Synthesis of donor monocomponent:
after synthesis of the donor and acceptor fragments, the donor fragments were sucked out by syringe into the reaction tube of the polymer acceptor and the reflux reaction was continued with stirring in an oil bath at 110 ℃ for 24 h. After the reaction is finished, injecting the polymer into methanol for sedimentation, carrying out suction filtration, sequentially extracting with n-hexane, acetone and dichloromethane, finally extracting with chloroform, collecting chloroform extracted products, and carrying out reduced pressure rotary evaporation on most of solvents.
Example 2
And (3) performance characterization of the single-component material of the donor polymer and preparation and test of the photovoltaic device.
The UV-visible absorption spectrum of the donor polymer monocomponent material was determined by an HP-8453 UV-visible spectrometer.
An organic solar cell device based on a donor monocomponent material comprising: an anode of Indium Tin Oxide (ITO) conductive glass, an anode modification layer, a photoactive layer, a cathode modification layer and a cathode. Wherein the anode modification layer is PEDOT/PSS (30 nm); the cathode modification layer is PDINN (30 nm), and the cathode is a deposition layer of Ag (100 nm); the active layer material is the donor monocomponent material PDCBT-bPYIT or PDCBT: PYIT (1:1.1).
Example 3
PDCBT:PYIT，PDCBT-bPhotophysical properties of PYIT and single component organic solar cell device properties.
The ultraviolet absorption spectrum of the PDCBT-PYIT in the solid mixed film is shown in figure 1. The absorption of PDCBT is mainly distributed between 390-650 nm and 680-nm-870 nm, the absorption peak of the donor is 526 nm, and the absorption peak of the receptor is 801-nm. PDCBT-bThe ultraviolet absorption spectrum of PYIT in a solid film is shown in fig. 2. PDCBT-bThe absorption of PYIT is mainly distributed between 380-640 nm and 680 nm-870 nm, with a donor absorption peak 519 nm and an acceptor absorption peak 812 nm.
PDCBT-bThe cyclic voltammogram of PYIT in a solid membrane is shown in figure 3. Exhibits reversible oxidation peak and reduction peak according to the calculation formula E HOMO = - (E ox +4.40) eV, giving its HOMO levels of-5.54, eV, respectively; according to the calculation formula E LUMO = - (E red +4.40) eV, giving their LUMO levels of-2.99 eV, respectively. From this, PDCBT-bThe electrochemical band gap of PYIT is 2.55 eV, respectively.
PDCBT PYIT (1:1.1, 14.7 mg/mL), its photovoltaic deviceJ-VThe curve is shown in fig. 5. The PDCBT-PYIT device shows good photovoltaicsCan have an open circuit voltage of 0.929V and a short circuit current of 14.74 mA/cm 2 The fill factor was 53.80% and the photoelectric conversion efficiency PCE was 7.35%. PDCBT-bIn the case of PYIT (16 mg/mL), its photovoltaic deviceJ-VThe curve is shown in fig. 6. PDCBT-bThe PYIT device exhibits good photovoltaic performance with an open circuit voltage of 0.936V and a short circuit current of 17.11 mA/cm 2 The fill factor was 52.91% and the photoelectric conversion efficiency PCE was 8.45%.
PDCBT, PDCBT PYIT and PDCBT-bSteady state Photoluminescence (PL) spectra of solid films of PYIT are shown in fig. 7, 8, pdcbt: PYIT, pdcbt-bThe fluorescence quenching efficiency of the PYIT solid film is 95.6% and 96.1%, respectively, and the fluorescence quenching efficiency of the single-component film is higher than that of the binary mixed film, which indicates that the exciton dissociation efficiency of the single-component device is higher, and the fluorescence quenching efficiency is one of reasons that the short-circuit current of the single-component device is higher than that of the binary device.
While the invention has been described in connection with the preferred embodiments, it is to be understood that the invention is not limited to the specific embodiments described above, but it is intended that the appended claims be construed to cover the scope of the invention. It will be appreciated by those skilled in the art that certain changes to the embodiments of the invention are to be made in light of the above teachings and are to be covered by the spirit and scope of the appended claims.
Claims (3)
1. A single-component block polymer photovoltaic material based on polythiophene donors is characterized by comprising the following molecular structures and derivatives thereof:
。
2. the method for preparing the single-component block polymer photovoltaic material based on the polythiophene donor as claimed in claim 1, which is characterized by comprising the following steps:
(1) Synthesis of the polymeric donor material PDCBT fragment: polymerizing raw materials of 5,5 '-bis (trimethylstannyl) -2,2' -bithiophene and 5, 5-dibromo- [2,2] -bithiophene-4, 4-dicarboxylic acid bis (2-butyl octyl) ester in solvent toluene to obtain a polymer donor PDCBT fragment;
(2) Synthesis of polymer acceptor material PYIT fragment: polymerizing raw materials of 2, 5-bis (trimethylstannyl) thiophene and Y5-2Br in toluene solvent to obtain a polymer acceptor PYIT fragment;
(3) Donor polymer monocomponent material PDCBT-bSynthesis of PYIT: transferring the polymer donor material PDCBT fragment obtained in the step (1) into a reaction tube of the polymer acceptor material PYIT fragment obtained in the step (2) by using a syringe, and continuing to polymerize to initially obtain a donor polymer monocomponent material PDCBT-b-PYIT; settling with methanol, suction filtering, sequentially extracting with n-hexane, acetone, dichloromethane and chloroform, purifying with silica gel chromatographic column, concentrating, settling, and suction filtering to obtain final product, namely the single component polymer material PDCBT-b-PYIT.
3. The use of a single-component block polymer photovoltaic material based on a polythiophene donor as claimed in claim 1 as photoactive layer material for the preparation of single-component organic solar devices.
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| CN202311674159.7A CN117820610A (en) | 2023-12-07 | 2023-12-07 | Single-component block polymer photovoltaic material based on polythiophene donor, and preparation method and application thereof |
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