CN113527328A - Small molecule donor compound for organic solar cell and preparation method and application thereof - Google Patents

Small molecule donor compound for organic solar cell and preparation method and application thereof Download PDF

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CN113527328A
CN113527328A CN202110954362.4A CN202110954362A CN113527328A CN 113527328 A CN113527328 A CN 113527328A CN 202110954362 A CN202110954362 A CN 202110954362A CN 113527328 A CN113527328 A CN 113527328A
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蔡松明
陆仕荣
徐静静
胡超
胡定琴
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Chongqing Institute of Green and Intelligent Technology of CAS
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Abstract

The invention relates to a small molecular donor compound for an organic solar cell, and a preparation method and application thereof, and belongs to the technical field of compound preparation. The micromolecule electron donor material has excellent stability and solution processability, can form excellent phase separation behavior with organic micromolecule acceptor materials, realizes the photoelectric conversion efficiency of about 13 percent in the all-micromolecule solar cell, can be suitable for the spin coating and printing processing technology of the organic solar cell, is not limited to the organic solar cell, and is also suitable for other photovoltaic devices.

Description

Small molecule donor compound for organic solar cell and preparation method and application thereof
Technical Field
The invention belongs to the technical field of compound preparation, and relates to a small molecular donor compound for an organic solar cell, and a preparation method and application thereof.
Background
The energy is a cornerstone developed by the modern science and technology society, and in the accelerating development of the past decades, the problems of climate change, environmental pollution, fossil fuel exhaustion and the like are brought by the continuous development and utilization of the traditional non-renewable energy by the human society. Therefore, the human demand for renewable energy sources such as solar energy, wind energy, tidal energy, nuclear energy and the like is increasing day by day, and the renewable energy sources are converted into electric energy and then applied, so that the traditional non-renewable energy sources can be gradually replaced.
Organic solar cells are attracting attention due to their advantages such as low cost, portability, flexibility, wearability, and large-area printing preparation. Wherein, the micromolecule material has the advantages of high purity, definite molecular structure and molecular weight, small batch difference of materials, high mobility, low energy disorder degree and the like; therefore, the all-small-molecule organic solar cell is expected to obtain higher photovoltaic efficiency. However, the problems of the absorption spectrum range of the active layer in the organic solar cell structure, the energy level matching between the donor and the acceptor, and the anisotropy of the donor and the acceptor face a great challenge, so that the high efficiency of the all-small-molecule organic solar cell is difficult to achieve.
Fluorine atoms have strong electron-withdrawing ability, and the absorption spectrum of the material can be widened and the molecular energy level can be finely adjusted by accurately regulating and controlling the substitution position and the substitution number of the fluorine atoms in the small molecular donor material, so that the short-circuit current and the open-circuit voltage of the device can be improved; more importantly, when the fluorinated small-molecule donor material is combined with a non-fullerene small-molecule receptor material, the blending morphology of the fluorinated small-molecule donor material can also be accurately regulated and controlled by the substitution position and the substitution number of fluorine atoms, which is mainly caused by the influence of introduced fluorine atoms on the characteristics of molecular accumulation, crystallinity, conformation stability and the like.
Therefore, it becomes important to develop a simple molecular design strategy to effectively adjust the light absorption range, energy level and crystallization property of the photoactive material, so as to realize the synergistic modulation of short-circuit current, open-circuit voltage and blending morphology.
Disclosure of Invention
In view of the above, an object of the present invention is to provide a small molecule donor compound for organic solar cells; the second purpose of the invention is to provide a preparation method of the small molecular donor compound for the organic solar cell; the invention also aims to provide a small-molecule donor compound for an organic solar cell, which is applied to a photovoltaic device.
In order to achieve the purpose, the invention provides the following technical scheme:
1. a small molecule donor compound for an organic solar cell, the chemical structure of the donor compound is shown in structural formula I:
Figure BDA0003219862710000021
wherein X1、X2、X3And X4Is any one of H-, F-or Cl-, and X1、X2、X3Or X4At least one of them is F-or Cl-;
R1、R2、R3、R4、R5、R6、R7or R8Is any one or more of H-, a straight-chain alkyl group with 2-20 carbon atoms, a branched-chain alkyl group with 2-20 carbon atoms, a straight-chain alkoxy group with 2-20 carbon atoms or a branched-chain alkoxy group with 2-20 carbon atoms.
Preferably, the donor compounds include compounds of structural formulae I-1 to I-14:
Figure BDA0003219862710000022
Figure BDA0003219862710000031
Figure BDA0003219862710000041
Figure BDA0003219862710000051
further preferred, the donor compound comprises the following compounds:
Figure BDA0003219862710000052
Figure BDA0003219862710000061
Figure BDA0003219862710000071
2. a process for the preparation of the above donor compounds, said process having the general reaction formula:
Figure BDA0003219862710000072
preferably, the preparation method comprises the following steps:
(1) dissolving the reactant I in absolute water organic solvent, slowly adding n-BuLi at the temperature below-0 ℃ under the protection of inert gas, reacting for more than 20min, adding the reactant II, stirring at room temperature for reacting overnight, and continuously adding SnCl-2H the next day2O and HCl react until the color of a reaction system changes to brown, after the reaction is finished, water-insoluble organic solvent extraction, deionized water washing, drying of a drying agent and reduced pressure concentration are sequentially carried out until the drying is finished, and then column chromatography separation is carried out to obtain a white solid, namely an intermediate I;
(2) dissolving the intermediate I in absolute water organic solvent, slowly adding n-BuLi at the temperature below 0 ℃ under the protection of inert gas, reacting for more than 20min, adding Sn (CH) after the reaction system is bright yellow3)3And Cl, stirring at room temperature for reaction overnight, and after the reaction is finished, sequentially reactingExtracting with a water-insoluble organic solvent, washing with deionized water, drying with a drying agent, concentrating under reduced pressure to dryness, and recrystallizing to obtain a light yellow solid intermediate II;
(3) dissolving intermediate II and reactant III in common organic solvent, bubbling, exhausting gas, and adding Pd (PPh)3)4Stirring and refluxing under the protection of inert gas until a reaction system is yellow, concentrating under reduced pressure after the reaction is finished until the reaction system is dried, performing column chromatography separation, and washing with methanol after the column chromatography to obtain a red solid intermediate III;
(4) dissolving the intermediate III and the reactant IV in an organic solvent, dripping DBU under the protection of inert gas, reacting at room temperature until the color of the system is dark red, concentrating under reduced pressure after the reaction is finished, drying, separating by column chromatography, and washing by methanol after the column chromatography to obtain the purple black solid micromolecule donor compound shown in the structural formula I.
Further preferably, the reactant I, n-BuLi, the reactant II, SnCl-2H in the step (1)2The molar ratio of O to HCl is 1.0: 1.1-1.5: 0.4-0.6: 5-6: 5-7;
the intermediate I, n-BuLi and Sn (CH) in step (2)3)3The molar ratio of Cl is 1.0: 2.1-2.5
The intermediate II, the reactant III and Pd (PPh) in the step (3)3)4The molar ratio of (A) to (B) is 1.0: 2.0-2.4: 0.03-0.04;
the molar ratio of the intermediate III to the reactant IV to the DBU in the step (4) is 1.0: 9-11: 0.4-0.7;
in the steps (1), (2) and (4), the organic solvent is any one of tetrahydrofuran, dichloromethane, trichloromethane or toluene.
3. A process for the preparation of the above donor compounds, said process having the general reaction formula:
Figure BDA0003219862710000091
further preferably, the preparation method specifically comprises the following steps:
(1) dissolving the reactant V and the reactant VI in an absolute organic solvent, slowly adding n-BuLi under the conditions of the temperature of below 0 ℃ and the protection of inert gas for reaction for more than 40min, adding the reactant II, stirring at room temperature for reaction overnight, and continuously adding SnCl-2H the next day2O and HCl react until the color of a reaction system changes to brown yellow, the product is poured into water after the reaction is finished, then water-insoluble organic solvent is used for extraction, deionized water washing, drying of a drying agent and reduced pressure concentration are carried out in sequence until the product is dried, and then column chromatography separation is carried out to obtain a white solid intermediate IV;
(2) dissolving the intermediate IV in an absolute organic solvent, slowly adding n-BuLi at the temperature of below 0 ℃ under the protection of inert gas, reacting for more than 40min, adding Sn (CH) after the reaction system is bright yellow3)3Stirring at room temperature to react overnight, after the reaction is finished, sequentially extracting with a water-insoluble organic solvent, washing with deionized water, drying with a drying agent, and concentrating under reduced pressure to dryness, and recrystallizing to obtain a light yellow solid intermediate V;
(3) dissolving intermediate V and reactant III in common organic solvent, bubbling, exhausting gas, and adding Pd (PPh)3)4Stirring and refluxing the mixture under the protection of inert gas until a reaction system is yellow, concentrating the mixture under reduced pressure after the reaction is finished until the mixture is dried, performing column chromatography separation, and washing the mixture with methanol after the column chromatography to obtain a red solid intermediate VI;
(4) dissolving the intermediate VI and the reactant IV in an organic solvent, dripping DBU under the protection of inert gas, reacting at room temperature until the color of the system is dark red, concentrating under reduced pressure after the reaction is finished, drying, separating by column chromatography, washing by methanol after the column chromatography to obtain the purple black solid micromolecule donor compound shown in the structural formula I.
Further preferably, the reactant V, the reactant VI, the n-BuLi, the reactant II and the SnCl-2H in the step (1)2The molar ratio of O to HCl is 1.0:1.0: 2.2-2.6: 0.9-1.2: 5-6: 5-7;
the intermediates IV, n-BuLi and Sn (CH) in the step (2)3)3ClThe molar ratio of (A) to (B) is 1.0: 2.1-2.5
The intermediate V, the reactant III and Pd (PPh) in the step (3)3)4The molar ratio of (A) to (B) is 1.0: 2.0-2.4: 0.03-0.04;
the molar ratio of the intermediate VI to the reactant IV to the DBU in the step (4) is 1.0: 9-11: 0.4-0.7;
in the steps (1), (2) and (4), the organic solvent is any one of tetrahydrofuran, dichloromethane, trichloromethane or toluene.
4. The use of the above small molecule donor compounds in photovoltaic devices.
Preferably, the photovoltaic device is an organic solar cell.
The invention has the beneficial effects that:
the invention discloses a small molecular donor compound for an organic solar cell, which takes Benzodithiophene (BDT) substituted by phenyl side groups as a central unit, has higher rotation potential barrier and crystal characteristics compared with the common BDT central unit substituted by thiophene side groups in the prior art, and can obtain better and multi-layer phase separation blending morphology when assembled with a non-fullerene receptor to form a full small molecular organic solar cell; meanwhile, fluorine or chlorine atoms with strong electronegativity are introduced to two-dimensional phenyl groups on two sides of a BDT core unit, so that the energy level of a donor material can be finely adjusted, namely, molecules substituted by fluorine or chlorine can obtain a deeper highest occupied orbital (HOMO) energy level and a narrower band gap; in addition, fluorine or chlorine is introduced to enable the absorption spectrum of molecules to generate red shift, and good light absorption complementation is formed by the absorption band edges of non-fullerene acceptor materials; in addition, when the micromolecule donor compound is blended with a non-fullerene acceptor material to form an active layer, the multi-level phase morphology is regulated and controlled by the substitution position and the substitution number of fluorine or chlorine atoms on the phenyl group of the BDT unit side group (mainly caused by the synergistic effect of the fluorine or chlorine atoms on the two-dimensional conjugated phenyl side group on molecular accumulation, crystallinity and conformation stability), namely the controllable modulation of the morphology of the active layer is possible from the material design perspective. Therefore, when the small molecular donor compound disclosed by the invention is used for an organic solar cell, the photoelectric conversion efficiency of the organic solar cell can be effectively improved from multiple angles such as energy level matching, light absorption complementation, crystallization control, blended phase morphology and the like.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention. The objectives and other advantages of the invention may be realized and attained by the means of the instrumentalities and combinations particularly pointed out hereinafter.
Drawings
For the purposes of promoting a better understanding of the objects, aspects and advantages of the invention, reference will now be made to the following detailed description taken in conjunction with the accompanying drawings in which:
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a small molecule donor compound (C-2F) prepared in example 1;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the small molecule donor compound (C-4F) prepared in example 2;
FIG. 3 is an ultraviolet absorption spectrum of small molecule donors C-2F and C-4F (wherein the dotted line is in a solution state and the solid line is in a thin film state);
FIG. 4 is a schematic structural view of an organic solar cell device prepared in example 7;
FIG. 5 is a block diagram of a non-fullerene acceptor (N3).
Detailed Description
The embodiments of the present invention are described below with reference to specific embodiments, and other advantages and effects of the present invention will be easily understood by those skilled in the art from the disclosure of the present specification. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention. It should be noted that the drawings provided in the following embodiments are only for illustrating the basic idea of the present invention in a schematic way, and the features in the following embodiments and examples may be combined with each other without conflict.
Example 1
Preparing a small molecular donor compound for an organic solar cell, wherein the reaction formula is as follows:
Figure BDA0003219862710000121
the preparation method comprises the following steps:
(1) placing 1.0mol of the compound (reactant I) shown in the formula (16) in a three-neck flask filled with absolute tetrahydrofuran, slowly adding 1.3mol of n-BuLi into the flask at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then, 0.45mol of the compound represented by the formula (17) (reaction product II) was added thereto, the reaction was stirred at room temperature overnight, and the next day, 5.5mol of SnCl-2H was further added to the reaction flask2And reacting O and 6mol of HCl for 2 hours, pouring a product into water after the reaction is finished, sequentially extracting with dichloromethane, washing with deionized water, drying with anhydrous magnesium sulfate, concentrating under reduced pressure until the product is dried, and performing column chromatography separation (the eluent is petroleum ether). Finally obtaining a white solid (intermediate I), wherein the structural formula is shown as a formula (18), and the yield is 35%;
(2) 0.45mol of the compound represented by the formula (18) (intermediate I) was placed in a three-necked flask containing tetrahydrofuran in absolute water, and then 1.035mol of n-BuLi was slowly added to the flask at-78 ℃ under nitrogen protection to react for 1 hour, followed by addition of 1.0mol of Sn (CH)3)3And Cl, stirring at room temperature for reaction overnight, after the reaction is finished, sequentially extracting with dichloromethane, washing with deionized water, drying with anhydrous magnesium sulfate, concentrating under reduced pressure until the mixture is dried, and recrystallizing. Finally obtaining light yellow solid (intermediate II), wherein the structural formula is shown as a formula (19), and the yield is 70%;
(3) 0.3mol of the compound represented by the formula (19) (intermediate II) and 0.72mol of the compound represented by the formula (20) (reactant III) were charged into a three-necked flask containing toluene, sufficiently dissolved and bubbled with a purge gas for 20min, followed by addition of 0.01mol of Pd (PPh)3)4Stirring and refluxing for 24h at 110 ℃ in a reaction bottle under the protection of nitrogen, concentrating under reduced pressure until the reaction is finished, performing column chromatography separation (eluent ratio: petroleum ether and chloroform volume ratio is 1:3), and washing with methanol after column chromatography. Finally obtaining red solid(intermediate III) with a structural formula shown as formula (21) and a yield of 55%;
(4) placing 0.16mol of the compound shown in the formula (21) (intermediate III) and 1.6mol of the compound shown in the formula (22) (reactant IV) in a three-necked bottle filled with trichloromethane, dripping 0.08mol of DBU under the protection of nitrogen, reacting at room temperature for 3h, concentrating under reduced pressure until the reaction is finished, drying, performing column chromatography separation (eluent ratio: petroleum ether and trichloromethane volume ratio is 1:6), washing with methanol after column chromatography to obtain a purple black solid shown in the formula (23) (C-2F), wherein the yield is 60%, and the nuclear magnetic resonance hydrogen spectrum is shown in figure 1.
Example 2
Preparing a small molecular donor compound for an organic solar cell, wherein the reaction formula is as follows:
Figure BDA0003219862710000141
the preparation method comprises the following steps:
(1) placing 1.0mol of the compound shown in the formula (24) into a three-neck flask (reactant I) filled with absolute tetrahydrofuran, slowly adding 1.1mol of n-BuLi into the flask at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then adding 0.4mol of the compound shown as the formula (17) (reactant II), and stirring at room temperature for reaction overnight; the next day, 5mol SnCl-2H was added into the reaction flask2And reacting the obtained product with 5mol of HCl for 2 hours, pouring the obtained product into water after the reaction is finished, sequentially extracting the product by using dichloromethane, washing the product by using deionized water, drying the product by using anhydrous magnesium sulfate, concentrating the product under reduced pressure until the product is dried, and performing column chromatography separation (an eluent is petroleum ether). Finally obtaining a white solid (intermediate I), wherein the structural formula is shown as a formula (25), and the yield is 35%;
(2) placing 0.45mol of the compound (intermediate I) shown in the formula (25) into a three-neck flask filled with absolute tetrahydrofuran, slowly adding 0.945mol of n-BuLi into the flask at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then 0.945mol of Sn (CH) is added3)3And Cl, stirring at room temperature for reaction overnight, after the reaction is finished, sequentially extracting with dichloromethane, washing with deionized water, drying with anhydrous magnesium sulfate, concentrating under reduced pressure to dryness, and repeatingCrystallizing to obtain light yellow solid (intermediate II) with a structural formula shown in formula (26) and a yield of 70%;
(3) adding 0.3mol of the compound shown in the formula (26) (intermediate II) and 0.6mol of the compound shown in the formula (20) (reactant III) into a three-necked bottle filled with toluene, fully dissolving and bubbling for exhausting for 20 min; then 0.009mol of Pd (PPh) was added3)4Stirring and refluxing for 24h at 110 ℃ in a reaction bottle under the protection of nitrogen. After the reaction is finished, concentrating under reduced pressure to dry, performing column chromatography separation (eluent ratio: petroleum ether and trichloromethane volume ratio is 1:3), and washing with methanol after column chromatography to obtain red solid (intermediate III) with a structural formula shown in formula (27) and a yield of 55%;
(4) 0.16mol of the compound represented by the formula (27) (intermediate III) and 1.44mol of the compound represented by the formula (22) (reactant IV) were placed in a three-necked flask containing chloroform, and 0.064mol of DBU was added dropwise under nitrogen protection, followed by reaction at room temperature for 3 hours. After the reaction is finished, concentrating under reduced pressure to dryness, performing column chromatography separation (eluent ratio: petroleum ether and chloroform volume ratio is 1:6), and washing with methanol after column chromatography. Finally, violet black solid formula (28) (C-4F) was obtained in 60% yield, and its nuclear magnetic hydrogen spectrum is shown in FIG. 2.
FIG. 3 shows UV absorption spectra of small molecule donors C-2F and C-4F (wherein the dotted line is in solution state and the solid line is in film state), and it can be seen from FIG. 3 that the number of fluorine atoms introduced into the phenyl side group has a significant effect on the absorption spectrum of the donor molecule, and the absorption spectrum of C-4F is red-shifted compared to C-2F, and forms a good absorption complementary with the absorption band edge of the non-fullerene acceptor material.
Example 3
Preparing a small molecular donor compound for an organic solar cell, wherein the reaction formula is as follows:
Figure BDA0003219862710000161
the preparation method comprises the following steps:
(1) 1.0mol of the compound represented by the formula (29) (reactant I) was placed in a reaction vessel containing tetrahydrofuran absolute waterSlowly adding 1.5mol of n-BuLi into the bottle at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then adding 0.6mol of the compound (reactant II) shown in the formula (17), and stirring at room temperature for reaction overnight; the next day, 6mol SnCl-2H was added into the reaction flask2O and 7mol of HCl are reacted for 2 hours, after the reaction is finished, the product is poured into water, extracted by dichloromethane, washed by deionized water, dried by anhydrous magnesium sulfate, decompressed and concentrated to be dried, and then column chromatography separation is carried out (eluent is petroleum ether), finally, white solid is obtained, the structural formula of which is shown as formula (30) (intermediate I), and the yield is 35%;
(2) placing 0.45mol of the compound (intermediate I) shown in the formula (30) into a three-neck flask filled with absolute tetrahydrofuran, slowly adding 1.125mol of n-BuLi into the flask at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then 1.125mol of Sn (CH) are added3)3Cl, stir reaction at room temperature overnight. After the reaction is finished, extracting by using dichloromethane, washing by using deionized water, drying by using anhydrous magnesium sulfate, decompressing and concentrating to be dried, and then recrystallizing. Finally obtaining light yellow solid (intermediate II), wherein the structural formula is shown as a formula (31), and the yield is 70%;
(3) adding 0.3mol of the compound shown in the formula (31) (intermediate II) and 0.72mol of the compound shown in the formula (20) (reactant III) into a three-necked bottle filled with toluene, fully dissolving and bubbling for exhausting for 20 min; then 0.012mol of Pd (PPh) were added3)4Stirring and refluxing for 24h at 110 ℃ in a reaction bottle under the protection of nitrogen. After the reaction is finished, concentrating under reduced pressure to dry, performing column chromatography separation (eluent ratio: petroleum ether and trichloromethane volume ratio is 1:3), and washing with methanol after column chromatography to obtain red solid (intermediate III) with a structural formula shown in formula (32) and a yield of 55%;
(4) placing 0.16mol of the compound shown in the formula (32) (intermediate III) and 1.76mol of the compound shown in the formula (22) (reactant IV) in a three-necked flask filled with trichloromethane, dripping 0.112mol of DBU under the protection of nitrogen, reacting at room temperature for 3h, concentrating under reduced pressure until the reaction is finished, drying, performing column chromatography separation (eluent ratio: petroleum ether and trichloromethane volume ratio is 1:6), and washing with methanol after column chromatography. The final product was a violet black solid of formula (33) (C-2Cl) in 60% yield.
Example 4
Preparing a small molecular donor compound for an organic solar cell, wherein the reaction formula is as follows:
Figure BDA0003219862710000181
the preparation method comprises the following steps:
(1) placing 1.0mol of the compound (reactant I) shown in the formula (34) in a three-neck flask filled with absolute tetrahydrofuran, slowly adding n-BuLi into the flask at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then adding 0.45mol of the compound (reactant II) shown in the formula (17), and stirring at room temperature for reaction overnight; adding SnCl-2H into the reaction flask the next day2O and HCl react for 2 hours, after the reaction is finished, the product is poured into water, dichloromethane is used for extraction, deionized water is used for washing, anhydrous magnesium sulfate is used for drying, and after the drying, column chromatography separation is carried out (an eluent is petroleum ether), so that a white solid (an intermediate I) is obtained, the structural formula of the white solid is shown as a formula (35), and the yield is 35%;
(2) placing 0.45mol of the compound (intermediate I) shown in the formula (35) into a three-neck flask filled with absolute tetrahydrofuran, slowly adding n-BuLi into the flask at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then 1.0mol of Sn (CH) is added3)3Cl, stir reaction at room temperature overnight. After the reaction is finished, extracting by using dichloromethane, washing by using deionized water, drying by using anhydrous magnesium sulfate, decompressing and concentrating to be dried, and then recrystallizing. Finally obtaining light yellow solid (intermediate I), wherein the structural formula is shown as a formula (36), and the yield is 70%;
(3) adding 0.3mol of the compound shown in the formula (36) (intermediate I) and 0.78mol of the compound shown in the formula (20) (reactant III) into a three-necked bottle filled with toluene, fully dissolving and bubbling for exhausting for 20 min; then 0.015mol of Pd (PPh) was added3)4Stirring and refluxing at 110 deg.C for 24 hr under nitrogen protection, concentrating under reduced pressure to dry after reaction, separating by column chromatography (eluent ratio: petroleum ether and chloroform volume ratio is 1:3), and purifying by column chromatographyWashing with methanol to obtain red solid (intermediate III) with a structural formula shown in formula (37) and a yield of 55%;
(4) placing 0.16mol of the compound shown in the formula (37) (intermediate III) and 0.36mol of the compound shown in the formula (22) (reactant IV) in a three-neck flask filled with trichloromethane, dripping a little DBU under the protection of nitrogen, reacting at room temperature for 3h, after the reaction is finished, concentrating under reduced pressure to dry, performing column chromatography separation (eluent ratio: petroleum ether and trichloromethane volume ratio is 1:6), and washing with methanol after column chromatography to finally obtain a purple black solid with the structural formula shown in the formula (38) (C-4Cl) and the yield of 60%.
Example 5
Preparing a small molecular donor compound for an organic solar cell, wherein the reaction formula is as follows:
Figure BDA0003219862710000201
the preparation method comprises the following steps:
(1) placing 1.0mol of the compound shown in the formula (39) (reactant V) and 1.0mol of the compound shown in the formula (40) (reactant VI) in a three-neck flask filled with absolute tetrahydrofuran, slowly adding 2.2mol of n-BuLi into the three-neck flask at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then adding 0.9mol of the compound (reactant II) shown in the formula (17), and stirring at room temperature for reaction overnight; the next day, 5mol SnCl-2H was added into the reaction flask2O and 5mol of HCl, and reacting for 2 h. And pouring the product into water after the reaction is finished, sequentially extracting with dichloromethane, washing with deionized water, drying with anhydrous magnesium sulfate, concentrating under reduced pressure to dryness, and performing column chromatography separation (the eluent is petroleum ether) to obtain a white solid (an intermediate IV) with a structural formula shown in formula (41) and a yield of 30%.
(2) Placing 0.45mol of the compound (intermediate IV) shown in the formula (41) into a three-neck flask filled with absolute tetrahydrofuran, slowly adding 0.945mol of n-BuLi into the flask at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then 0.945mol of Sn (CH) is added3)3And (3) stirring and reacting the mixture at room temperature overnight, and after the reaction is finished, sequentially extracting the mixture by using dichloromethane, washing the mixture by using deionized water and carrying out anhydrous reactionThe mixture was dried over magnesium sulfate, concentrated under reduced pressure to dryness, and then recrystallized. Finally obtaining light yellow solid (intermediate V), the structural formula of which is shown as formula (42), and the yield is 60%.
(3) Adding 0.3mol of the compound shown in the formula (42) (intermediate V) and 0.6mol of the compound shown in the formula (20) (reactant III) into a three-necked bottle filled with toluene, fully dissolving and bubbling for exhausting for 20 min; then 0.009mol of Pd (PPh) was added3)4Stirring and refluxing for 24h at 110 ℃ in a reaction bottle under the protection of nitrogen. After the reaction is finished, concentrating under reduced pressure to dryness, performing column chromatography separation (eluent ratio: petroleum ether and trichloromethane volume ratio is 1:3), and washing with methanol after column chromatography to obtain red solid (intermediate VI), wherein the structural formula is shown as formula (43), and the yield is 55%.
(4) 0.16mol of the compound of formula (43) (intermediate VI) and 1.44mol of the compound of formula (22) (reactant IV) were placed in a three-necked flask containing chloroform, and 0.064mol of DBU was added dropwise under nitrogen protection, and the reaction was carried out at room temperature for 3 hours. After the reaction is finished, concentrating under reduced pressure to dryness, performing column chromatography separation (eluent ratio: petroleum ether and trichloromethane volume ratio is 1:6), and washing with methanol after column chromatography to obtain the purple black solid formula (44) (C-F-Cl) with the yield of 60%.
Example 6
Preparing a small molecular donor compound for an organic solar cell, wherein the reaction formula is as follows:
Figure BDA0003219862710000221
the preparation method comprises the following steps:
(1) placing 1.0mol of the compound shown in the formula (45) (reactant V) and 1.0mol of the compound shown in the formula (46) (reactant VI) in a three-neck flask filled with absolute tetrahydrofuran, slowly adding 2.6mol of n-BuLi into the three-neck flask at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then adding 1.2mol of the compound (reactant II) shown in the formula (17), and stirring at room temperature for reaction overnight; the next day, 6mol SnCl-2H was added into the reaction flask2O and 7mol of HCl, and reacting for 2 h. After the reaction is finished, pouring the product into water, and sequentially extracting and removing the product by using dichloromethaneWashing with ionized water, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and performing column chromatography separation (eluent is petroleum ether) to obtain white solid (intermediate IV) with a structural formula shown in formula (47) and a yield of 30%.
(2) Placing 0.45mol of the compound (intermediate IV) shown in the formula (47) into a three-neck flask filled with absolute tetrahydrofuran, slowly adding 1.125mol of n-BuLi into the flask at-78 ℃ under the protection of nitrogen, and reacting for 1 h; then 1.125mol of Sn (CH) are added3)3Cl, stir reaction at room temperature overnight. After the reaction is finished, extracting by using dichloromethane, washing by using deionized water, drying by using anhydrous magnesium sulfate, decompressing and concentrating to be dried, and then recrystallizing. Finally obtaining light yellow solid (intermediate V), the structural formula of which is shown as formula (48), and the yield is 60%.
(3) Adding 0.3mol of the compound shown in the formula (48) (intermediate V) and 0.72mol of the compound shown in the formula (20) (reactant III) into a three-necked bottle filled with toluene, fully dissolving and bubbling for exhausting for 20 min; then 0.012mol of Pd (PPh) were added3)4Stirring and refluxing for 24h at 110 ℃ in a reaction bottle under the protection of nitrogen. After the reaction is finished, concentrating under reduced pressure to dryness, carrying out column chromatography separation (eluent ratio: petroleum ether and trichloromethane volume ratio is 1:3), and washing with methanol after column chromatography. Finally, red solid (intermediate VI) is obtained, the structural formula of the red solid is shown as a formula (49), and the yield is 55%.
(4) 0.16mol of the compound represented by the formula (49) (intermediate VI) and 1.176mol of the compound represented by the formula (22) (reactant IV) were placed in a three-necked flask containing chloroform, and 0.112mol of DBU was added dropwise under nitrogen protection, followed by reaction at room temperature for 3 hours. After the reaction is finished, concentrating under reduced pressure to dryness, performing column chromatography separation (eluent ratio: petroleum ether and chloroform volume ratio is 1:6), and washing with methanol after column chromatography. The final product was a violet black solid of formula (50) (C-2F-2Cl) in 60% yield.
Through the synthesis procedures in the above examples 1 to 6, it can be seen that: reacting X in the formula1、X3Replacement of a hydrogen atom of (A) by another F-or Cl-, X2、X4By replacement of fluorine atoms of (a) with other H-or Cl- (wherein X1、X2、X3Or X4At least one of them is F-or Cl-), R1、R5The 2-ethylhexyl group is replaced by any one of H-, a linear alkyl group having 2 to 20 carbon atoms, a branched alkyl group having 2 to 20 carbon atoms, a linear alkoxy group having 2 to 20 carbon atoms or a branched alkoxy group having 2 to 20 carbon atoms, R2，R3、R4、R6、R7、R8And replacing the n-hexyl with any one of other H-, linear alkyl with 2-20 carbon atoms, branched alkyl with 2-20 carbon atoms, linear alkoxy with 2-20 carbon atoms or branched alkoxy with 2-20 carbon atoms to obtain the micromolecule donor compound for the organic solar cell shown in the structural formula I.
Example 7
The product of formula (28) (C-4F) prepared in example 2 was used to prepare a forward organic solar cell device, which was prepared as follows:
(1) cleaning of ITO (indium tin oxide) glass: respectively ultrasonically cleaning ITO glass by using deionized water, acetone and isopropanol for 30 minutes, and then treating the ITO glass in a plasma cleaner for 5 minutes;
(2) spin-coating PEDOT/PSS with the thickness of 10nm on the cleaned ITO glass;
(3) spin coating a photoactive layer: the Donor material consists of the small molecule Donor material synthesized in the example 2 (namely, the compound C-4F shown in the formula (28)) and a non-fullerene Acceptor (N3) (the mass ratio of the formula (28) (C-4F) to the (N3) is 1.5:1), specifically, the C-4F and the N3 are dissolved in chlorobenzene or chloroform to form a solution with the concentration of 20mg/mL, and the solution method is adopted to spin-coat the solution on a PEDOT/PSS layer to form a photoactive layer (Donor/Acceptor) with the thickness of 120 nm;
(4) preparing an electron transport layer by spin coating: on top of the active layer, Phen-NaDPO (available from Aldrich) was spin-coated to form an electron transport layer (PNDIT-F3N/PSS) having a thickness of 30 nm;
(5) and evaporating a metal silver electrode on the Phen-NaDPO electron transport layer to form a metal Ag electrode (Cathodode/Ag) with the thickness of 100 nm.
The structure of the prepared organic solar cell device is shown in fig. 4.
Example 8
The product of formula (28) (C-4F) prepared in example 2 was used to prepare a forward organic solar cell device, which was prepared as follows:
(1) cleaning of ITO (indium tin oxide) glass: respectively ultrasonically cleaning ITO glass by using deionized water, acetone and isopropanol for 30 minutes, and then treating the ITO glass in a plasma cleaner for 5 minutes;
(2) spin-coating PEDOT/PSS with the thickness of 30nm on the cleaned ITO glass;
(3) spin coating a photoactive layer: the material consists of the small molecular donor material synthesized in the example 2 (namely, the compound C-4F shown in the formula (28)) and a non-fullerene acceptor (N3) (the mass ratio of the formula (28) (C-4F) to the (N3) is 1:1), specifically, the C-4F and the N3 are dissolved in chlorobenzene or chloroform to form a solution with the concentration of 20mg/mL, and the solution method is adopted to spin-coat the solution on a PEDOT/PSS layer to form a photoactive layer with the thickness of 110 nm;
(4) preparing an electron transport layer by spin coating: on the active layer, Phen-NaDPO (available from Aldrich) was spin-coated to form an electron transport layer having a thickness of 10 nm;
(5) and (3) evaporating a metal silver electrode on the Phen-NaDPO electron transport layer to form a metal electrode with the thickness of 90 nm.
Example 9
The product of formula (28) (C-4F) prepared in example 2 was used to prepare a forward organic solar cell device, which was prepared as follows:
(1) cleaning of ITO (indium tin oxide) glass: respectively ultrasonically cleaning ITO glass by using deionized water, acetone and isopropanol for 30 minutes, and then treating the ITO glass in a plasma cleaner for 5 minutes;
(2) spin-coating PEDOT/PSS with the thickness of 30nm on the cleaned ITO glass;
(3) spin coating a photoactive layer: the donor material consists of the small molecule donor material synthesized in the example 2 (namely, the compound C-4F shown in the formula (28)) and a non-fullerene acceptor (N3) (the mass ratio of the formula (28) (C-4F) to the non-fullerene acceptor (N3) (the structure of which is shown in figure 5) is 1.6:1), specifically, C-4F and N3 are dissolved in chlorobenzene or chloroform to form a solution with the concentration of 20mg/mL, and the solution method is adopted to spin-coat the solution on a PEDOT/PSS layer to form a photoactive layer with the thickness of 115 nm;
(4) preparing an electron transport layer by spin coating: on the active layer, Phen-NaDPO (available from Aldrich) was spin-coated to form an electron transport layer having a thickness of 50 nm;
(5) and (3) evaporating a metal silver electrode on the Phen-NaDPO electron transport layer to form a metal electrode with the thickness of 95 nm.
Testing the performance of the forward organic solar cell device:
the forward direction organic solar cell devices prepared in examples 7 to 9 were subjected to performance tests, and the obtained results are shown in table 1.
TABLE 1 forward organic solar cell device Performance test
Figure BDA0003219862710000251
From the test results in table 1, it can be seen that for different donor-acceptor ratios and active layer thicknesses, the impact on the photoelectric conversion efficiency, these slight effects may result from the degree of donor-acceptor phase separation in the active layer and the morphology of the active layer.
In summary, the small molecule electron donor material of the present invention has excellent stability and solution processability, can form an excellent phase separation behavior with an organic small molecule acceptor material, realizes about 13% of photoelectric conversion efficiency in an all small molecule solar cell, and is applicable to spin coating and printing processes of organic solar cells, and certainly, is not limited to organic solar cells, and is also applicable to other photovoltaic devices.
Finally, the above embodiments are only intended to illustrate the technical solutions of the present invention and not to limit the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that modifications or equivalent substitutions may be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions, and all of them should be covered by the claims of the present invention.

Claims (10)

1. A small molecule donor compound for an organic solar cell, characterized in that the chemical structure of the donor compound is shown in formula I:
Figure FDA0003219862700000011
wherein X1、X2、X3And X4Is any one of H-, F-or Cl-, and X1、X2、X3Or X4At least one of them is F-or Cl-;
R1、R2、R3、R4、R5、R6、R7or R8Is any one or more of H-, a straight-chain alkyl group with 2-20 carbon atoms, a branched-chain alkyl group with 2-20 carbon atoms, a straight-chain alkoxy group with 2-20 carbon atoms or a branched-chain alkoxy group with 2-20 carbon atoms.
2. The donor compound of claim 1, wherein the donor compound comprises compounds of structural formulae I-1 to I-14:
Figure FDA0003219862700000012
Figure FDA0003219862700000021
Figure FDA0003219862700000031
Figure FDA0003219862700000041
3. a process for the preparation of a donor compound according to any one of claims 1 to 2, characterized in that the reaction formula of the process is as follows:
Figure FDA0003219862700000051
4. the method of claim 3, comprising the steps of:
(1) dissolving the reactant I in absolute water organic solvent, slowly adding n-BuLi at the temperature below-0 ℃ under the protection of inert gas, reacting for more than 20min, adding the reactant II, stirring at room temperature for reacting overnight, and continuously adding SnCl-2H the next day2O and HCl react until the color of a reaction system changes to brown, after the reaction is finished, water-insoluble organic solvent extraction, deionized water washing, drying of a drying agent and reduced pressure concentration are sequentially carried out until the drying is finished, and then column chromatography separation is carried out to obtain a white solid, namely an intermediate I;
(2) dissolving the intermediate I in absolute water organic solvent, slowly adding n-BuLi at the temperature below 0 ℃ under the protection of inert gas, reacting for more than 20min, adding Sn (CH) after the reaction system is bright yellow3)3Stirring and reacting at room temperature overnight, after the reaction is finished, sequentially extracting with a water-insoluble organic solvent, washing with deionized water, drying with a drying agent, concentrating under reduced pressure to dryness, and recrystallizing to obtain a light yellow solid intermediate II;
(3) dissolving intermediate II and reactant III in common organic solvent, bubbling, exhausting gas, and adding Pd (PPh)3)4Stirring and refluxing under the protection of inert gas until a reaction system is yellow, concentrating under reduced pressure after the reaction is finished until the reaction system is dried, performing column chromatography separation, and washing with methanol after the column chromatography to obtain a red solid intermediate III;
(4) dissolving the intermediate III and the reactant IV in an organic solvent, dripping DBU under the protection of inert gas, reacting at room temperature until the color of the system is dark red, concentrating under reduced pressure after the reaction is finished, drying, separating by column chromatography, and washing by methanol after the column chromatography to obtain the purple black solid micromolecule donor compound shown in the structural formula I.
5. The method according to claim 4, wherein the reactant I, n-BuLi, the reactant II, SnCl-2H in the step (1)2The molar ratio of O to HCl is 1.0: 1.1-1.5: 0.4-0.6: 5-6: 5-7;
the intermediate I, n-BuLi and Sn (CH) in step (2)3)3The molar ratio of Cl is 1.0: 2.1-2.5
The intermediate II, the reactant III and Pd (PPh) in the step (3)3)4The molar ratio of (A) to (B) is 1.0: 2.0-2.4: 0.03-0.04;
the molar ratio of the intermediate III to the reactant IV to the DBU in the step (4) is 1.0: 9-11: 0.4-0.7;
in the steps (1), (2) and (4), the organic solvent is any one of tetrahydrofuran, dichloromethane, trichloromethane or toluene.
6. A process for the preparation of a donor compound according to any one of claims 1 to 2, characterized in that the reaction formula of the process is as follows:
Figure FDA0003219862700000071
7. the preparation method according to claim 6, characterized in that the preparation method specifically comprises the steps of:
(1) dissolving the reactant V and the reactant VI in an absolute organic solvent, slowly adding n-BuLi under the conditions of the temperature of below 0 ℃ and the protection of inert gas for reaction for more than 40min, adding the reactant II, stirring at room temperature for reaction overnight, and continuously adding SnCl-2H the next day2O and HCl react until the color of the reaction system changes to brown yellow, the product is poured into water after the reaction is finished, and then water-insoluble organic solvents are used for extraction in sequence,Washing with deionized water, drying with a drying agent, concentrating under reduced pressure to dryness, and performing column chromatography separation to obtain a white solid intermediate IV;
(2) dissolving the intermediate IV in an absolute organic solvent, slowly adding n-BuLi at the temperature of below 0 ℃ under the protection of inert gas, reacting for more than 40min, adding Sn (CH) after the reaction system is bright yellow3)3Stirring at room temperature to react overnight, after the reaction is finished, sequentially extracting with a water-insoluble organic solvent, washing with deionized water, drying with a drying agent, and concentrating under reduced pressure to dryness, and recrystallizing to obtain a light yellow solid intermediate V;
(3) dissolving intermediate V and reactant III in common organic solvent, bubbling, exhausting gas, and adding Pd (PPh)3)4Stirring and refluxing the mixture under the protection of inert gas until a reaction system is yellow, concentrating the mixture under reduced pressure after the reaction is finished until the mixture is dried, performing column chromatography separation, and washing the mixture with methanol after the column chromatography to obtain a red solid intermediate VI;
(4) dissolving the intermediate VI and the reactant IV in an organic solvent, dripping DBU under the protection of inert gas, reacting at room temperature until the color of the system is dark red, concentrating under reduced pressure after the reaction is finished, drying, separating by column chromatography, washing by methanol after the column chromatography to obtain the purple black solid micromolecule donor compound shown in the structural formula I.
8. The method according to claim 7, wherein the reactant V, the reactant VI, the n-BuLi, the reactant II, the SnCl-2H in the step (1)2The molar ratio of O to HCl is 1.0:1.0: 2.2-2.6: 0.9-1.2: 5-6: 5-7;
the intermediates IV, n-BuLi and Sn (CH) in the step (2)3)3The molar ratio of Cl is 1.0: 2.1-2.5
The intermediate V, the reactant III and Pd (PPh) in the step (3)3)4The molar ratio of (A) to (B) is 1.0: 2.0-2.4: 0.03-0.04;
the molar ratio of the intermediate VI to the reactant IV to the DBU in the step (4) is 1.0: 9-11: 0.4-0.7;
in the steps (1), (2) and (4), the organic solvent is any one of tetrahydrofuran, dichloromethane, trichloromethane or toluene.
9. Use of a small molecule donor compound according to claims 1-2 in a photovoltaic device.
10. Use according to claim 9, wherein the photovoltaic device is an organic solar cell.
CN202110954362.4A 2021-08-19 2021-08-19 Small molecule donor compound for organic solar cell and preparation method and application thereof Pending CN113527328A (en)

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