CN114605435A - Photoelectric and photothermal conversion material containing condensed ring electron-withdrawing end group and preparation method and application thereof - Google Patents
Photoelectric and photothermal conversion material containing condensed ring electron-withdrawing end group and preparation method and application thereof Download PDFInfo
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 239000003446 ligand Substances 0.000 claims abstract description 11
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 8
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims abstract description 7
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- 239000002994 raw material Substances 0.000 claims description 6
- 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 claims description 6
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
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Abstract
The invention belongs to the field of organic semiconductor materials, and discloses a photoelectric and photothermal conversion material containing condensed ring electron-withdrawing end groups, and a preparation method and application thereof. The material is based on an acceptor-donor-acceptor (A-D-A) structure, when the material is prepared, 3-bromofluorene-9-ketone and a fused ring electron-withdrawing end group compound containing monobromide are prepared by using active methylene, pyridine and titanium tetrachloride, and a palladium catalyst and a ligand are added to prepare the material through a stille coupling reaction, so that the material not only has the advantages of simple synthesis method, high yield, low cost and the like, but also has strong absorption in the range of 700-1100 nm, and the band gap is larger than that of the materialAnd (3) narrow. The energy conversion efficiency of the organic solar cell based on the material as an acceptor is 0.40-0.43%; the material shows good photo-thermal conversion performance, and the power is 0.8W/cm2The temperature can be quickly raised to 180 ℃ under the laser irradiation of 808nm, and the composite material has excellent circulating photo-thermal stability and bleaching resistance.
Description
Technical Field
The invention belongs to the field of organic semiconductor materials, and particularly relates to a preparation method and application of a photoelectric and photothermal conversion material containing a condensed ring electron-withdrawing end group.
Background
Organic solar cells have attracted extensive attention and research due to their unique advantages of being lightweight, flexible, solution processable, and the like. In recent years, the development of non-fullerene receptors has made record of the photoelectric conversion efficiency of organic solar cells to be new and higher, and now, the photoelectric conversion efficiency of organic solar cells is more than 19%. However, such high-performance non-fullerene receptors are generally constructed by condensation reaction of active methylene groups on electron-withdrawing units and aldehyde groups in electron-donating units, and this synthesis method allows an unstable exocyclic carbon-carbon double bond to exist in a molecule, and electrical cyclization reaction is easily caused under the action of light to degrade, thereby causing the reduction of the morphological stability of an active layer and the stability of a device. Therefore, in order to fundamentally solve the stability problem of the receptor, new molecular design and strategy are urgently needed to synthesize an electron receptor with good stability.
The photothermal conversion material is a material for converting near infrared light into heat energy through non-radiative transition, and has potential application prospects in the fields of seawater desalination, photothermal therapy, photothermal catalysis and the like. Traditional inorganic photothermal materials such as graphene, gold nanomaterials and the like contain expensive and non-degradable metals although the photothermal conversion efficiency is high; however, organic two-dimensional frame materials and organic polymer photothermal materials also have problems of high synthesis cost and low reproducibility.
Therefore, the organic conjugated micromolecule photo-thermal material has the advantages of definite structure, simple synthesis, low toxicity and the like, and is widely concerned. At present, organic small molecules are mostly based on donor (D) -acceptor (a) type molecular structures to broaden spectrum absorption in the near infrared region, but because the types of acceptor units with strong electron-withdrawing ability are relatively few, reports of efficient photothermal conversion materials based on organic small molecules are not many.
The Chinese patent application 202110255570.5 discloses a non-doped hole transport material based on a condensed ring electron-withdrawing parent nucleus, and a synthesis method and application thereof, wherein diazosulfide multi-condensed rings with electron-withdrawing capability are used as parent nuclei, and good photoelectric conversion efficiency can be obtained when the material is applied to a perovskite solar cell. However, the terminal group of the material has weak electron-withdrawing ability, higher energy level and wider band gap, can not reach a near infrared region by absorption, and is not suitable for the fields of organic solar cell receptors and photo-thermal conversion.
Disclosure of Invention
Aiming at the defects and shortcomings of the prior art, the invention mainly aims to provide the photoelectric and photothermal conversion material containing the condensed ring electron-withdrawing end group, which has a narrow band gap, strong absorption in the range of 700-1100 nm and small polarity.
The invention also aims to provide a preparation method of the photoelectric and photothermal conversion material containing the condensed ring electron withdrawing end group, which is simple, high in yield and easy to purify.
The invention further aims to provide application of the photoelectric and photothermal conversion material containing the condensed ring electron-withdrawing end group in the fields of organic solar cells and photothermal conversion.
The purpose of the invention is realized by the following technical scheme:
a photoelectric and photothermal conversion material containing condensed ring electron-withdrawing end groups takes an electron-donating unit D as a core, and two ends of the electron-donating unit D are coupled with an electron-withdrawing unit A through a single bond to form an A-D-A structure;
the electron-withdrawing unit A is used as an acceptor group, and the structural general formula is as follows:
wherein, X represents halogen atoms F, Cl, Br or H, and Ar represents a benzene ring or a thiophene ring.
The electron-donating unit D is used as a donor group and is one of the following chemical structural formulas:
wherein R is1Is H, C1-C16Straight chain alkane of (2)Base, C3-C20Branched alkyl or C6-C12Phenyl of (2); r2Is C1-C16Straight chain alkyl group of (1), C1-C12Linear alkoxy of (C)3-C20Branched alkyl of C3-C20Branched alkoxy of C6-C12A phenyl group of (a).
For further purposes of the present invention, R is preferred1Is one of the following chemical structural formulas:
preferably R2Is one of the following chemical structural formulas:
preferably, the electron-withdrawing unit A is one of the following chemical structural formulas:
preferably, the photoelectric and photothermal conversion material containing the fused ring electron withdrawing end group has one of the chemical structural formulas of LY1, LY2, LY3 and LY 4:
the preparation method of the photoelectric and photothermal conversion material containing the condensed ring electron withdrawing end group comprises the following steps of:
(1) adding 3-bromofluorene-9-ketone and an electron-withdrawing unit with active methylene into a dry reaction container, adding a first organic solvent for dissolving, dripping pyridine and titanium tetrachloride, heating and refluxing for 30 min-4 h at 50-150 ℃, and preparing a condensed ring electron-withdrawing terminal group compound containing monobromine;
(2) taking an alkyl tin compound (electron donor unit) and the terminal group compound in the step 1) as raw materials, adding a palladium catalyst and a ligand, adding a second organic solvent for dissolving, heating and refluxing for 8-24 h at 90-130 ℃ under the protection of nitrogen or argon, and preparing the photoelectric and photothermal conversion material containing the condensed ring electron-withdrawing terminal group through Stille coupling; the alkyl tin compound is selected from an electron donor unit trimethyl tin compound or an electron donor unit tributyltin compound.
Preferably, the molar ratio of the 3-bromofluorene-9-ketone to the electron-withdrawing unit with the active methylene in the step (1) is 1: 1-1: 2.
Preferably, the amount of the pyridine and the titanium tetrachloride in the step (1) is 3-10 times of the molar amount of the 3-bromofluorene-9-one.
Preferably, the molar ratio of the alkyl tin compound to the terminal compound in the step (2) is 1:2 to 1: 3.
Preferably, in the step (2), the palladium catalyst is selected from at least one of tetratriphenylphosphine palladium, palladium acetate, palladium/carbon and bistriphenylphosphine dichloride for neutralizing tris (dibenzylideneacetone) dipalladium, the ligand is selected from one of tris (o-methylphenyl) phosphine, triphenylphosphine and tricyclohexylphosphine, the amount of the palladium catalyst is 1 to 15 percent of the molar amount of the alkyl tin compound, and the amount of the ligand is 3 to 45 percent of the molar amount of the alkyl tin compound.
Preferably, the first organic solvent and the second organic solvent in steps (1) and (2) are one or a mixture of more than two of toluene, chlorobenzene, tetrahydrofuran and chloroform.
The photoelectric and photothermal conversion material containing the condensed ring electron-withdrawing end group is applied to the preparation of organic solar cells; the photoelectric and photothermal conversion material based on the condensed ring electron-withdrawing end group is applied to an organic solar cell as an electron acceptor.
The photo-thermal conversion material containing the condensed ring electron-withdrawing end group has the following advantages and beneficial effects:
(1) the fused ring electron-withdrawing terminal group compound has the advantages of simple synthesis method, high yield, small polarity and easy purification;
(2) the fused ring electron-withdrawing end group compound is coupled with the electron-donating unit alkyl tin compound through a single bond, so that the photoelectric and photothermal conversion material with excellent photothermal stability is prepared, the production cost is low, the band gap is narrow, and the strong absorption is realized within the range of 700-1100 nm. The energy conversion efficiency of the organic solar cell based on the material as an acceptor is 0.40-0.43%; the adopted power is 0.8W/cm2The 808nm laser irradiates sample powder, the powder can be rapidly heated and kept stable within 20s, the highest temperature can reach 180 ℃, and good photo-thermal stability and bleaching resistance are shown.
Drawings
Fig. 1 is a uv-vis-nir spectrum of the photoelectric and photothermal conversion material synthesized in example 1.
Fig. 2 is a cyclic voltammogram of the photoelectric and photothermal conversion material synthesized in example 1.
FIG. 3 is a graph showing a thickness of 0.8W/cm of the photoelectric and photothermal conversion material synthesized in example 12Temperature rise/fall curve under laser excitation of power.
Fig. 4 shows the cyclic photothermal stability of the photoelectric and photothermal conversion material synthesized in example 1.
FIG. 5 is a nuclear magnetic hydrogen spectrum of product LY1 of example 1.
Detailed Description
For a better understanding of the present invention, the present invention will be further described with reference to the following examples and drawings, but the embodiments of the present invention are not limited thereto.
Example 1:
3-bromofluorene-9-ketone is used as a raw material to synthesize the photoelectric and photothermal conversion material LY1, and the reaction equation is as follows:
(1) 3-Bromofluoren-9-one (100mg,0.39mmol), 5, 6-dichloro-3-methyl-ethyl acetate were added to a dry reaction vessel- (dicyanomethylene) inden-1-one (113mg,0.43mmol) and tetrahydrofuran (15mL) as a solvent were stirred well, and then 0.2mL of pyridine and 0.2mL of a titanium tetrachloride solution were added thereto, followed by heating and refluxing at 60 ℃ for 1 hour. After the reaction is finished, the reaction product is cooled to room temperature, ice water is added for quenching, dichloromethane is used for extraction for three times, an organic layer is collected, the solvent is removed through rotary evaporation, and the residue is separated and purified through a silicon-based chromatographic column, petroleum ether/dichloromethane (1:1vo1/vol) is used as an eluent, and vacuum drying is carried out to obtain 153mg of fused ring electron withdrawing end-group compound A1 (red solid, yield 77.6%). The hydrogen spectrum of the product results in:1H-NMR(CDCl3,500MHz)δ8.60(d,J＝8.0Hz,1H),8.46(d,J＝8.4Hz,1H),8.01(d,J＝1.6Hz,1H),7.65(m,2H),7.48(m,2H),7.43–7.39(m,2H)。
(2) a condensed ring electron-withdrawing terminal compound A1(82mg,0.162mmol), 6,12, 12-tetra (4-hexylphenyl) -6, 12-dihydrobithiophene [2,3-d:2',3' -d ']-s-indeno [1,2-b:5,6-b']Bithiophene-2, 8-bistrimethyltin (IDTT-Sn) (100mg,0.074mmol), the catalyst tris (dibenzylideneacetone dipalladium) (6.9mg,0.0074mmol), the ligand tris (o-methylphenyl) phosphine (6.8mg,0.0222mmol) and the solvent toluene (15mL) were added to a reaction vessel, stirred well under nitrogen and at room temperature, then heated to 110 ℃ for 10 h. After the reaction is finished, the reaction product is cooled to room temperature, dichloromethane is used for extraction for three times, an organic layer is collected, the solvent is removed by rotary evaporation, and the residue is separated and purified by a silica-based chromatographic column, petroleum ether/dichloromethane (1:2vo1/vol) is used as an eluent, and vacuum drying is carried out to obtain 104mg of a photoelectric and photothermal conversion material LY1 (dark solid, yield 75.4%). The hydrogen spectrum of the product results in:1H-NMR(500MHz,CDCl3)δ8.63(d,J＝11.8Hz,2H),8.47(m,2H),7.98(m,2H),7.75(d,J＝4.2Hz,2H),7.65–7.54(m,6H),7.45–7.31(m,6H),7.25–7.09(m,18H),2.58(m,8H),1.60(m,8H),1.28(m,24H),0.86(m,12H)。
the ultraviolet-visible-near infrared absorption spectrum of the photoelectric and photothermal conversion material synthesized by the embodiment is shown in fig. 1, and the film has strong absorption in the range of 700-1100 nm; the cyclic voltammogram is shown in FIG. 2, and the electrochemical band gap is only 1.10 eV.
The material synthesized by the embodiment is used as an electron acceptor to prepare the organic solar device with the structure of ITO/PEDOT, PSS/active layer/PDINO/AgAnd (4) a positive battery. And (2) ultrasonically cleaning the glass/ITO substrate by using a semiconductor cleaning solution, deionized water and isopropanol for 20 minutes respectively, then moving the glass/ITO substrate into an oven to dry at the temperature of 80 ℃, and then performing O2plasma cleaning treatment. Then, spin-coating a cavity transport layer PEDOT (Poly ethylene glycol ether ketone) PSS aqueous solution on the ITO at the speed of 3000rpm, and carrying out thermal annealing treatment at 150 ℃ for 10 min; then, a mixed solution of PBDB-T or PM6 and LY1 prepared in example 1 was spin-coated thereon, the solvent was chloroform, 0.5% volume fraction of 1-chloronaphthalene was added as an additive, the total concentration of the solution was 16mg/ml, the weight ratio of donor to acceptor was 1:1.2, the rotation speed was 3000r/min, and annealing treatment was carried out at 80 ℃ for 10min to obtain an active layer blend film having a thickness of about 100 nm; then, spin-coating PDINO solution with the concentration of 1mg/ml on the active layer at the speed of 3000rpm as an electron transport layer; finally, at pressures below 2X 10-6Evaporating a layer of Ag with a thickness of 100nm under mbar vacuum, wherein the shape and area of each electrode are controlled by a mask plate and are 0.0514cm2。
The illumination intensity is 100mW/cm2AM1.5 of (1), as shown in table 1, the energy conversion efficiency of the organic solar cell based on LY1 of example 1 as the receptor was 0.40% to 0.43%.
TABLE 1
The material synthesized in the example is used as an electron acceptor and is used as a photo-thermal conversion material, and the power used is 0.8W/cm2The 808nm laser irradiates the sample powder, and an infrared thermal imager is adopted to record the temperature rise process. The sample powder rapidly warmed up and remained stable within 20s, with a maximum temperature of up to 180 deg.c (fig. 3). As shown in fig. 4, during the multiple rounds of repeated turning on/off of the laser, the temperature rise and fall of the sample powder are close, no photobleaching occurs, and good light stability is shown.
The results show that the inherent molecular structure stability of the photoelectric material containing the condensed ring electron-withdrawing end group is beneficial to improving the light stability of the material, has application potential as an organic solar cell receptor, and has wide application prospect in the field of photo-thermal conversion.
Example 2:
3-bromofluorene-9-ketone is used as a raw material to synthesize a photoelectric and photothermal conversion material LY2, and the reaction equation is as follows:
(1) in a dry reaction vessel, 3-bromofluoren-9-one (280mg,1.08mmol), 5, 6-difluoro-3- (dicyanomethylene) inden-1-one (300mg,1.29mmol) and tetrahydrofuran (40mL) as a solvent were added, and after stirring well, 0.6mL of pyridine and 0.6mL of a titanium tetrachloride solution were added, and heated under reflux at 70 ℃ for 2 hours. After the reaction is finished, cooling to room temperature, adding ice water for quenching, extracting for three times by dichloromethane, collecting an organic layer, removing the solvent by rotary evaporation, separating and purifying the residue by using a silicon-based chromatographic column, taking petroleum ether/dichloromethane (1:1vo1/vol) as an eluent, and drying in vacuum to obtain 480mg of fused ring electron withdrawing end-group compound A2 (red solid, yield 84.2%). The hydrogen spectrum of the product results in:1H-NMR(CDCl3,500MHz)δ8.47(d,J＝8.4Hz,1H),8.40(m,1H),7.75(m,1H),7.68(m,1H),7.62(d,J＝1.9Hz,1H),7.49(m,1H),7.44–7.38(m,2H),7.25–7.23(m,1H).
(2) mixing condensed ring electron-withdrawing end group compound A2(38mg,0.081mmol), 6,12, 12-tetra (4-hexylphenyl) -6, 12-dihydrodithiophene [2,3-d:2',3' -d ']-s-indeno [1,2-b:5,6-b']Bithiophene-2, 8-bistrimethyltin (IDTT-Sn) (50mg,0.037mmol), the catalyst tris (dibenzylideneacetone dipalladium) (3.4mg,0.0037mmol), the ligand tris (o-methylphenyl) phosphine (3.4mg,0.0111mmol) and the solvent toluene (12mL) were added to a reaction vessel, stirred well under nitrogen and at room temperature, then heated to 110 ℃ for 12 h. After the reaction is finished, the reaction product is cooled to room temperature, dichloromethane is used for extraction for three times, an organic layer is collected, the solvent is removed by rotary evaporation, and the residue is separated and purified by a silica-based chromatographic column, petroleum ether/dichloromethane (1:2vo1/vol) is used as an eluent, and vacuum drying is carried out to obtain 45mg of a photoelectric and photothermal conversion material LY2 (dark solid, yield 67.6%). The hydrogen spectrum of the product results in:1H-NMR(CDCl3,500MHz)δ8.49(m,2H),7.84–7.70(m,4H),7.64(m,2H),7.24–7.06(m,30H),2.58(m,8H),1.60(m,8H),1.40–1.11(m,24H),0.86(m,12H).
example 3:
the fused ring electron-withdrawing end-group compound a2 in example 2 was used as a raw material to synthesize a photoelectric and photothermal conversion material LY3, and the reaction equation was:
adding a condensed ring electron withdrawing end group compound A2(97mg,0.206mmol), 4,9, 9-tetraoctyl-4, 9-dihydro-s-indolo [1,2-b:5,6-b' ] dithiophene-2, 7-bistrimethyltin (IDT-Sn) (80mSg,0.086mmol), a catalyst of dibenzylidene acetone dipalladium (7.8mg,0.0086mmol), a ligand of tris (o-methylphenyl) phosphine (8.1mg,0.0258mmol) and a solvent of toluene (16mL) into a reaction vessel, stirring uniformly at room temperature under the protection of nitrogen, and then heating to 110 ℃ for reaction for 12 h. After the reaction is finished, the solution is cooled to room temperature, dichloromethane is used for extraction for three times, an organic layer is collected, the solvent is removed by rotary evaporation, and the residue is separated and purified by a silica-based chromatographic column, petroleum ether/dichloromethane (1:2vo1/vol) is used as an eluent, and vacuum drying is carried out to obtain 62mg of photoelectric and photothermal conversion material LY3 (dark solid, yield is 52.1%).
Example 4:
the fused ring electron-withdrawing end-group compound a2 in example 2 was used as a raw material to synthesize a photoelectric and photothermal conversion material LY4, and the reaction equation was:
the fused ring electron withdrawing terminal compound A2(53mg,0.113mmol), 12, 13-bis (2-butyloctyl) -3, 9-diundecyl-12, 13-dihydro- [1,2,5] thiadiazole [3,4-e ] thieno [2 ", 3": 4',5' ] thieno [2',3':4,5] pyrrolo [3,2-g ] thieno [2',3':4,5] thieno [3,2-b ] indole-2, 10-bistrimethyltin (BTP-Sn) (70mg,0.054mmol), the catalyst tris-dibenzylideneacetone dipalladium (4.9mg,0.0054mmol), the ligand tris (o-methylphenyl) phosphine (5.1mg,0.0162mmol) and the solvent toluene (16mL) were added to a reaction vessel, stirring the mixture evenly at room temperature under the protection of nitrogen, and then heating the mixture to 110 ℃ for reaction for 24 hours. After the reaction is finished, the reaction product is cooled to room temperature, dichloromethane is used for extraction for three times, an organic layer is collected, the solvent is removed by rotary evaporation, and the residue is separated and purified by a silica-based chromatographic column, petroleum ether/dichloromethane (1:2vo1/vol) is used as an eluent, and vacuum drying is carried out to obtain 54mg of a photoelectric and photothermal conversion material LY4 (dark solid, yield is 56.1%).
It should be noted that the embodiments of the present invention are not limited by the above-mentioned examples, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents and are included in the scope of the present invention.
Claims (10)
1. A photoelectric and photothermal conversion material containing condensed ring electron-withdrawing end groups is characterized in that an electron-donating unit D is taken as a core, and two ends of the electron-donating unit D are coupled with an electron-withdrawing unit A through a single bond to form an A-D-A structure;
the electron-withdrawing unit A is used as an acceptor group, and the structural general formula is as follows:
wherein X is halogen atoms F, Cl, Br or H, and Ar is a benzene ring or a thiophene ring;
the electron-donating unit D is used as a donor group and is one of the following chemical structural formulas:
wherein R is1Is H, C1-C16Straight chain alkyl group of (1), C3-C20Branched alkyl or C6-C12Phenyl of (a); r2Is C1-C16Straight chain alkyl group of (1), C1-C12Linear alkoxy of (C)3-C20Is supported byChain alkyl radical, C3-C20Branched alkoxy of C6-C12A phenyl group of (a).
2. The photoelectric and photothermal conversion material having condensed ring electron-withdrawing end group according to claim 1, wherein R is1Is one of the following chemical structural formulas:
3. the photoelectric and photothermal conversion material having condensed ring electron-withdrawing end group according to claim 1, wherein R is2Is one of the following chemical structural formulas:
4. the photoelectric and photothermal conversion material having fused ring electron-withdrawing end group according to claim 1, wherein said electron-withdrawing unit a is one of the following chemical structural formulas:
5. the photoelectric and photothermal conversion material having a condensed ring electron withdrawing terminal group according to claim 1, wherein the photoelectric and photothermal conversion material having a condensed ring electron withdrawing terminal group has one of the chemical structural formulae LY1, LY2, LY3, and LY 4:
6. the method for producing a photoelectric and photothermal conversion material having a condensed ring electron-withdrawing terminal group according to claim 1, comprising the steps of:
1) adding 3-bromofluorene-9-ketone and an electron-withdrawing unit with active methylene into a dry reaction container, adding a first organic solvent for dissolving, dripping pyridine and titanium tetrachloride, and heating and refluxing at 50-150 ℃ to prepare a condensed ring electron-withdrawing end group compound containing monobromo;
2) taking an alkyl tin compound and the fused ring electron-withdrawing end group compound in the step 1) as raw materials, adding a palladium catalyst and a ligand, adding a second organic solvent for dissolving, heating and refluxing at 90-130 ℃ under the protection of nitrogen or argon, and performing Stille coupling to prepare the photoelectric and photo-thermal conversion material containing the fused ring electron-withdrawing end group; the alkyl tin compound is selected from an electron-donating unit trimethyl tin compound or an electron-donating unit tributyltin compound.
7. The method for preparing a photoelectric and photothermal conversion material having a condensed ring electron-withdrawing end group according to claim 6, wherein said palladium catalyst is at least one selected from the group consisting of tetrakistriphenylphosphine palladium, palladium acetate, palladium/carbon, and bis-triphenylphosphine palladium dichloride and tris-dibenzylideneacetone dipalladium; the ligand is selected from one of tri (o-methylphenyl) phosphine, triphenylphosphine and tricyclohexylphosphine; the dosage of the palladium catalyst is 1 to 15 percent of the molar weight of the alkyl tin compound, and the dosage of the ligand is 3 to 45 percent of the molar weight of the alkyl tin compound.
8. The preparation method of the photoelectric and photothermal conversion material containing the condensed ring electron-withdrawing end group according to claim 6, wherein the molar ratio of the 3-bromofluoren-9-one to the electron-withdrawing unit with the active methylene group is 1: 1-1: 2; the molar ratio of the alkyl tin compound of the electron donor unit to the terminal compound is 1: 2-1: 3.
9. The method for preparing a photoelectric and photothermal conversion material containing a fused ring electron-withdrawing end group according to claim 6, wherein the first organic solvent and the second organic solvent are one or a mixture of two or more of toluene, chlorobenzene, tetrahydrofuran and chloroform; the using amount of the pyridine and the titanium tetrachloride is 3-10 times of the molar weight of the 3-bromofluorene-9-ketone; the heating reflux time at 50-150 ℃ is 30 min-4 h; the heating reflux time at 90-130 ℃ is 8-24 h.
10. Use of the photoelectric and photothermal conversion material containing the condensed ring electron withdrawing end group as recited in any one of claims 1 to 5 in the preparation of an organic solar cell.
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