CN109824709B - Sulphthalocyanine acceptor material, synthesis method and application in solar cell - Google Patents
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Abstract
A sub-phthalocyanine receptor material, a synthetic method and application in solar cells are disclosed, wherein imide groups are introduced into unsubstituted sub-phthalocyanines to synthesize a series of novel receptor materials with adjustable solubility and proper LUMO energy level. The material takes 4, 5-dicyano-benzene imide and boron trichloride as raw materials, the raw materials are stirred and reacted in an organic solvent at a certain temperature to generate chloro-subphthalocyanine, and then the chloro-subphthalocyanine is substituted by fluorine, phenoxy or p-methoxy-thiophenyl. The receptor molecular material designed and synthesized by the invention has very excellent photoelectric performance, and in a bulk heterojunction solar cell, the device structure requirement is simple, and the photoelectric conversion efficiency is as high as 4.92%.
Description
Technical Field
The invention belongs to the technical field of organic synthesis and photoelectricity, and particularly relates to a subphthalocyanine acceptor material, a synthesis method and application in a solar cell
Background
With social progress and human development, the energy problem is becoming more and more severe, and solar energy is widely used by human as a clean and pollution-free renewable energy source. Bulk heterojunction organic solar cells have the following advantages compared to widely used inorganic solar cells: the solution processing with low cost can prepare flexible wearable equipment, and has various types and properties.
The active layer material is a key factor in determining the performance of bulk heterojunction solar cells. The active layer material is obtained by solution blending and spin coating of an organic acceptor material and an organic donor material. The donor materials are multiple in types and excellent in performance, the matched acceptor materials are few in types and poor in performance, and the development of bulk heterojunction solar cells is restricted by the lack of the excellent acceptor materials.
The subphthalocyanine is a phthalocyanine compound with a bowl-shaped conjugated framework, which is composed of three isoindole units, and the central atom is boron. Three isoindoles are connected with boron atoms to form a conjugated system with an inner layer of 14 pi electrons. All reports in the literature indicate that the subphthalocyanine central atom is a boron atom and the axial ligands are generally halogen atoms, alkoxy derivatives. The subphthalocyanine molecules have aromaticity, high stability and strong visible absorption, but the unsubstituted subphthalocyanine has the defects of poor solubility, high LUMO energy level (-3.56eV) and difficult separation and purification, and is not suitable for being used as an acceptor material of a bulk heterojunction solar cell.
Disclosure of Invention
The invention aims to provide a subphthalocyanine acceptor material, a synthetic method and application in a solar cell, wherein three imide groups are introduced into a conjugated parent of subphthalocyanine, so that the LUMO energy level of molecules is obviously reduced, the electron accepting capability of the molecules is enhanced, and the target molecules are suitable for the acceptor material due to the appropriate energy level (-3.91-3.98 eV); the solubility of the molecule is adjusted by changing the alkyl chain on the N atom of the imide group, so that the imide group can be processed in a solution. The target molecule can be used as a receptor material of a bulk heterojunction solar cell and has excellent performance.
The invention is realized by the following technical scheme.
The general structural formula of the subphthalocyanine receptor material is shown as the following formula:
wherein R is C4-C30Linear, branched alkanes or aromatic hydrocarbons of (a); x is Cl, F, phenoxy or p-methoxyphenylthio.
The invention relates to a method for synthesizing a subphthalocyanine receptor material, which is characterized by comprising the following steps:
when X is Cl for substitution, 4, 5-dicyano benzene imide and boron trichloride are mixed according to the molar ratio of 1: 1-20, and are stirred and reacted for 10 min-2 h in an organic solvent at a certain temperature to generate chloro phthalocyanine imide; when X is F substitution, the chloro phthalocyanine triacyimide and the silver tetrafluoroborate are mixed according to the molar ratio of 1: 1-10, and the mixture is stirred and reacted for 1-20 hours at room temperature in an organic solvent to obtain fluoro phthalocyanine triacyimide; when X is substituted by phenoxy, mixing chlorinated phthalocyaninylene triacyimide, phenol and pyridine according to the molar ratio of 1: 1-20: 1-100, and stirring and reacting in an organic solvent at a certain temperature for 1-30 h to obtain phenoxy substituted phthalocyaninylene triacyimide; when X is p-methoxyphenylthio, chlorinated phthalocyaninetriimide, p-methoxyphenylthiol, silver trifluoromethanesulfonate and triethylamine are mixed according to the molar ratio of 1: 1-20: 1-100, and the mixture is stirred and reacted for 1-30 hours at a certain temperature in an organic solvent to obtain the thiophenyl substituted phthalocyaninetriimide.
The organic solvent is o-xylene, o-dichlorobenzene, p-xylene, m-xylene or mesitylene.
The certain temperature is from room temperature to the reflux temperature of the solvent.
The raw materials 1, 2-dimethyl-4, 5-dibromobenzene, boron trichloride, silver tetrafluoroborate, p-methoxythiophenol and the like used in the invention are all commercial products, and 4, 5-dicyanobenzimide is prepared according to a literature method (chem. Mater.2008,20, 6889-.
The compound provided by the invention is applied to an active layer material in the field of bulk heterojunction organic solar cells.
The invention has the beneficial effects that: 1. the introduction of imide groups on the conjugated parent of the subphthalocyanine obviously reduces the LUMO energy level of the molecule from-3.56 eV to about-3.95 eV; 2. the solubility of molecules is adjusted by different alkyl chains on an N atom of an imide group, so that the molecules can be well dissolved in organic solvents such as chloroform, chlorobenzene and the like; 3. the synthesized subphthalocyanine compound is used as a receptor material in a bulk heterojunction solar cell, and the photoelectric conversion efficiency of the synthesized subphthalocyanine compound reaches 4.92 percent.
The solar cell in the invention adopts a compound 5 as an acceptor material, a commercial polymer PM6 (the structure is shown in the attached figure 2) as a donor material, and adopts a reversed phase structure: ITO/ZnO (30nm)/PM6 Compound 5(120nm)/MoO3(7nm)/Ag(100nm)。
Drawings
Fig. 1 is a solar cell device structure of the present invention.
Figure 2 is a graph based on compound 5: J-V plot of organic solar cell device of polymer PM 6.
Detailed Description
The synthesis of the subphthalocyanine receptor material according to the present invention is further illustrated below with reference to the following specific examples, but the scope of the present invention is not limited thereto.
Example 1: synthesis of Compound 1.
BCl is added into a 10mL two-mouth bottle under the protection of argon3(5mL, 1M solution in p-xylene) and Compound a (1.27g, 5mmol) were reacted at 170 ℃ for 30min, quenched, cooled to room temperature, the solvent removed by rotary evaporation, and CHCl3The resulting purple solid was further recrystallized from glacial acetic acid to give 1 as a purple solid (0.67g, 46%).1H NMR(400MHz,CDCl3)δ:9.32(s,6H),3.82(t,6H),1.77(m,6H),1.26(m,6H),0.99(t,9H)ppm；13C NMR(100MHz,CDCl3)δ:166.9,150.6,134.5,133.6,118.4,38.5,30.6,20.1,13.6ppm；MALDI-TOF-MS(ESI),Calcd for C42H34BClN9O6 805.2335,found:805.2334(M-)。
Example 2: synthesis of Compound 2.
BCl is added into a 10mL two-mouth bottle under the protection of argon3(3mL of a 1M solution in p-xylene) and compound b (0.70g, 2mmol) were reacted at 170 ℃ for 30min, the reaction was stopped, cooled to room temperature, the solvent was removed by rotary evaporation, and CH was used2Cl2PE (v: v ═ 1:1) was used as an eluent column to obtain a purple solid, which was further recrystallized from glacial acetic acid to obtain a purple solid 2(0.39g, 52%).1H NMR(400MHz,CDCl3)δ:9.31(s,6H),4.25(m,3H),2.09(m,6H),1.75(m,6H),1.26(m,36H),0.82(t,18H)ppm；13C NMR(100MHz,CDCl3)δ:167.3,150.5,134.5,133.3,118.3,53.2,32.3,31.4,26.4,22.5,13.9ppm；MALDI-TOF-MS(ESI),Calcd for C63H76BClN9O6 1099.5622,found:1099.5622(M-)。
Example 3: synthesis of Compound 3.
BCl is added into a 10mL two-mouth bottle under the protection of argon3(5.5mL of a 1M solution in p-xylene) and compound c (2.0g, 5mmol) were reacted at 170 ℃ for 30min, the reaction was stopped, cooled to room temperature, the solvent was removed by rotary evaporation, and CH was used2Cl2PE (v: v ═ 1:1) was used as an eluent column to obtain a purple solid, which was further recrystallized from glacial acetic acid to obtain a purple solid 3(0.39g, 52%).1H NMR(400MHz,CDCl3)δ:9.52(s,6H),7.52(t,3H),7.39(d,3H),7.31(d,3H),2.91(m,3H),2.61(m,3H),1.31(d,18H),1.09(d,18H)ppm；13C NMR(100MHz,CDCl3)δ:166.8,150.6,147.1,146.8,134.8,133.2,130.5,126.6,124.2,124.0,119.3,29.6,29.4,24.0,23.8ppm；MALDI-TOF-MS(ESI),Calcd for C42H34BClN9O6 1117.4213,found:1117.4210(M-).
Example 4: synthesis of Compound 4.
BCl is added into a 10mL two-mouth bottle under the protection of argon3(5mL, 1M solution in p-xylene) and compound d (1.55g, 5mmol) were reacted at 170 ℃ for 30min, the reaction was stopped, cooled to room temperature, the solvent was removed by rotary evaporation, and CHCl was used3The resulting purple solid was further recrystallized from glacial acetic acid to give a purple solid 4(0.71g, 49%).1H NMR(400MHz,CDCl3)δ:9.32(s,6H),3.82(t,6H),1.77(m,6H),1.26(m,30H),0.99(t,9H)ppm；13C NMR(100MHz,CDCl3)δ:166.9,150.6,134.5,133.6,118.4,38.5,30.6,20.1,13.6ppm；HRMS(ESI),Calcd for C54H58BClN9O6 974.4286,found:974.4292(M-)。
Example 5: synthesis of Compound 5.
Under the protection of argon, a 10mL two-neck bottle is filled with a compound 1(200mg, 0.25mmol) and a compound AgBF4(96mg, 0.49mmol), 3ml of dry toluene, reaction at room temperature for 6h, stopping the reaction, removing the solvent by rotary evaporation, and reacting with CH2Cl2THF (v: v 300:1) was used as eluent column separation to obtain purple solid, which was further recrystallized with glacial acetic acid to obtain purple solid 5(0.53g, 53%).1H NMR(400MHz,CDCl3)δ:9.33(s,6H),4.25(m,3H),2.09(m,6H),1.75(m,6H),1.26(m,36H),0.82(t,18H)ppm；13C NMR(100MHz,CDCl3)δ:167.3,150.5,134.5,133.3,118.3,53.2,32.3,31.4,26.4,22.5,13.9ppm；MALDI-TOF-MS(ESI),Calcd for C63H76BBrN9O6 789.2631,found:789.2631(M-)。
Example 6: synthesis of Compound 6.
Under the protection of argon, a 10mL two-neck bottle is filled with a compound 2(200mg, 0.25mmol) and a compound AgBF4(71mg, 0.36mmol), 3ml of dry toluene, reaction at room temperature for 6h, stopping the reaction, removing the solvent by rotary evaporation, and reacting with CH2Cl2PE (v: v ═ 1:1) was separated on a column as an eluent to give a purple solid, which was further recrystallized from glacial acetic acid to give a purple solid 6(0.53g, 53%).1H NMR(400MHz,CDCl3)δ:9.33(s,6H),4.25(m,3H),2.09(m,6H),1.75(m,6H),1.26(m,36H),0.82(t,18H)ppm；13C NMR(100MHz,CDCl3)δ:167.3,150.5,134.5,133.3,118.3,53.2,32.3,31.4,26.4,22.5,13.9ppm；MALDI-TOF-MS(ESI),Calcd for C63H76BBrN9O6 789.2631,found:789.2631(M-)。
Example 7: synthesis of Compound 7.
Under the protection of argon, a 10mL two-neck bottle is filled with a compound 3(180mg,0.16mmol) and a compound AgBF4(156mg,0.8mmol), dry toluene 4ml, react at room temperature for 7h, stop the reaction, remove the solvent by rotary evaporation, use CH2Cl2PE (v: v ═ 3:1) was used as an eluent column to give a purple solid, which was further recrystallized from glacial acetic acid to give 7(120mg, 68%) a purple solid.1H NMR(400MHz,CDCl3)δ:9.50(s,6H),7.52(t,3H),7.39(d,3H),7.30(d,3H),2.92(dt,3H),2.58(dd,3H),1.31(d,18H),1.08(d,18H)ppm；13C NMR(100MHz,CDCl3)δ:166.9,151.9,147.1,146.8,134.7,134.7,133.1,130.5,126.5,124.2,124.1,119.3,29.6,29.4,24.1,23.8ppm；MALDI-TOF-MS(ESI),Calcd for C66H57BFN9O61101.4509,found:1102.4529(M-)。
Example 8: synthesis of Compound 8.
Under the protection of argon, a 10mL two-neck bottle is filled with a compound 4(300mg,0.31mmol) and a compound AgBF4(120mg,0.61mmol), dry toluene 4ml, react at room temperature for 7h, stop the reaction, remove the solvent by rotary evaporation, use CH2Cl2PE (v: v ═ 3:1) was used as an eluent column to give a purple solid, which was further recrystallized from glacial acetic acid to give a purple solid 8(120mg, 54%).1H NMR(400MHz,CDCl3)δ:9.44(s,6H),3.88(t,6H),1.76(m,6H),1.26(m,30H),0.99(t,9H)ppm；13C NMR(100MHz,CDCl3)δ:166.9,150.6,134.5,133.6,118.4,38.5,30.6,20.1,13.6ppm；HRMS(ESI),Calcd for C54H58BFN9O6957.4509,found:957.4522(M-)。
Example 9: synthesis of Compound 9.
Adding compound 1(400mg, 0.5mmol), phenol (467.04mg,5mmol), pyridine (0.2mL,2.48mmol) and 8mL toluene into a 25mL two-neck flask under the protection of argon, reacting at 140 deg.C for 15h, stopping reaction, cooling to room temperature, removing solvent by rotary evaporation, and adding CH2Cl2THF (v: v 300:1) was used as eluent column separation to obtain purple solid, which was further recrystallized with glacial acetic acid to obtain purple solid 9(195mg, 50%).1H NMR(400MHz,CDCl3)δ:9.29(s,6H),6.79(t,2H),6.70(d,1H),5.38(d,2H),3.81(t,6H),1.75(m,6H),1.45(m,6H),0.98(d,9H)ppm；13C NMR(100MHz,CDCl3)δ:167.0,151.8,134.4,133.3,129.2,122.4,118.8,118.2,38.4,30.5,20.1,13.5ppm；MALDI-TOF-MS(ESI),Calcd for C48H38BN9O7 863.2987,found 863.2945(M-)。
Example 10: synthesis of Compound 10.
Under the protection of argon, compound 2(200mg, 0.18mmol), phenol (171mg,1.82mmol), pyridine (0.073mL,0.9mmol) and 5mL of toluene are added into a 25mL two-port bottle to react at 140 ℃ for 15h, the reaction is stopped, the temperature is cooled to room temperature, the solvent is removed by rotary evaporation, and CH is used2Cl2THF (v: v 300:1) was used as eluent column separation to obtain purple solid, which was further recrystallized with glacial acetic acid to obtain purple solid 10(95mg, 45%).1H NMR(400MHz,CDCl3)δ:9.27(s,6H),6.77(t,2H),6.72(d,1H),5.44(d,2H),4.25(m,3H),2.09(m,6H),1.75(m,6H),1.26(m,36H),0.82(t,18H)ppm；13C NMR(100MHz,CDCl3)δ:167.03,151.82,134.42,133.32,129.21,122.42,118.86,53.2,32.3,31.4,26.4,22.5,13.9ppm；MALDI-TOF-MS(ESI),Calcd for C69H80BN9O71157.6274,found 1157.6211(M-)。
Example 11: synthesis of Compound 11.
Adding compound 3(200mg, 0.18mmol), phenol (171mg,1.81mmol), pyridine (0.073mL,0.9mmol) and 5mL toluene into a 25mL two-neck flask under the protection of argon, reacting at 140 deg.C for 15h, stopping reaction, cooling to room temperature, removing solvent by rotary evaporation, and adding CH2Cl2PE (v: v ═ 3:2) was used as an eluent column to give a purple solid, which was further recrystallized from glacial acetic acid to give 11(95mg, 46%) a purple solid.1H NMR(400MHz,CDCl3)δ:9.53(s,6H),7.55(t,3H),7.33(d,3H),7.29(d,3H),6.79(t,2H),6.71(d,1H),5.36(d,2H),2.91(m,3H),2.61(m,3H),1.31(d,18H),1.09(d,18H)ppm；13C NMR(100MHz,CDCl3)δ:166.8,150.6,147.1,146.8,134.8,133.2,130.5,129.2,126.6,124.2,124.0,122.4,119.3,118.8,29.6,29.4,24.0,23.8ppm；MALDI-TOF-MS(ESI),Calcd for C42H34BClN9O6 1175.4865,found:1175.4810(M-)。
Example 12: synthesis of Compound 12.
Adding compound 4(300mg,0.31mmol), phenol (295mg,1.81mmol), pyridine (0.126mL,1.57mmol) and 5mL toluene into a 25mL two-neck flask under the protection of argon, reacting at 140 deg.C for 15h, stopping reaction, cooling to room temperature, removing solvent by rotary evaporation, and adding CH2Cl2THF (v: v 150:1) was used as eluent column separation to obtain purple solid, which was further recrystallized with glacial acetic acid to obtain purple solid 12(95mg, 46%).1H NMR(400MHz,CDCl3)δ:9.56(s,6H),6.77(t,2H),6.72(d,1H),5.34(d,2H),3.84(t,6H),1.73(m,6H),1.22(m,30H),0.98(t,9H)ppm；13C NMR(100MHz,CDCl3)δ:166.9,150.6,134.5,133.6,129.21,122.4,119.3,118.8,118.4,38.5,30.6,20.1,13.6ppm；HRMS(ESI),Calcd for C60H62BN9O7 1031.4865,found:1031.4833(M-)。
Example 13: synthesis of Compound 13.
Adding compound 1(200mg, 0.25mmol), silver trifluoromethanesulfonate (318.8mg,1.24mmol) and 5mL of toluene in a 25mL two-neck flask under the protection of argon, reacting at 40 ℃ for 3h, adding p-methoxythiophenol (136.7mg, 1.24mmol) and triethylamine (160.3mg, 1.24mmol), heating to 90 ℃, reacting for 6h, stopping the reaction, cooling to room temperature, removing the solvent by rotary evaporation, and adding CH2Cl2THF (v: v 150:1) was used as eluent column separation to obtain purple solid, which was further recrystallized with glacial acetic acid to obtain purple solid 13(95mg, 42.6%).1H NMR(400MHz,CDCl3)δ:9.28(s,6H),6.76(s,1H),6.29(d,2H),5.31(d,2H),3.81(t,6H),3.56(s,3H),1.77(m,6H),1.42(t,6H),0.98(t,9H)ppm；13C NMR(100MHz,CDCl3)δ:166.9,150.6,134.5,133.6,129.2,122.4,119.3,118.8,118.4,40.86,38.5,30.6,20.1,13.6ppm；HRMS(ESI),Calcd for C49H40BN9O7S 909.2864found:909.2861(M-)。
The electron mobility of the pure film of the above prepared compounds 1,2, 5 and 6 was measured by Space Charge Limited Current (SCLC) method as shown in table 1 below. It can be seen that the electron mobility of compound 5 is much higher than that of the other compounds. The compound 5 has stronger electron transport capability.
TABLE 1
| Compound (I) | Film thickness/nm | Mobility/cm2V-1s-1 |
| 1 | 100 | 4.4×10-5 |
| 2 | 123 | 4.4×10-5 |
| 5 | 114 | 5.0×10-4 |
| 6 | 150 | 2.6×10-6 |
Bulk heterojunction solar cells were prepared with polymer PM6 (structural formula below) as the donor and compound 5 as the acceptor, and it was found that with 0.5% DIO addition, a thermal anneal at 100 ℃ was able to achieve a photoelectric conversion efficiency of 4.92%, corresponding to table 2.
TABLE 2
Claims (7)
1. A sub-phthalocyanine receptor material is characterized in that: has the following molecular structural formula:
wherein R is a straight chain or branched chain alkyl of C4-C11 and 2, 6-diisopropylphenyl; x is Cl, F, phenoxy or p-methoxyphenylthio.
2. The method for synthesizing a subphthalocyanine receptor material according to claim 1, wherein: and when X is Cl, stirring 4, 5-dicyano benzene imide and boron trichloride according to the molar ratio of 1: 1-20 in an organic solvent for reaction for 10 min-2 h at the reflux temperature of the solvent to generate chloro subphthalocyanine triacmide.
3. The method for synthesizing a subphthalocyanine receptor material according to claim 1, wherein: and when X is F, carrying out stirring reaction on chlorinated phthalocyaninetriimide and silver tetrafluoroborate for 1-20 h at room temperature in an organic solvent by using a formula of 1: 1-10 mol ratio to obtain fluorinated phthalocyaninetriimide.
4. The method for synthesizing a subphthalocyanine receptor material according to claim 1, wherein: when X is phenoxy, chloro phthalocyanine triacyimide, phenol and pyridine are mixed according to the molar ratio of 1: 1-20: 1-100, and are stirred and reacted for 1-30 h in an organic solvent at the reflux temperature of the solvent to obtain phenoxy substituted phthalocyanine triacyimide.
5. The method for synthesizing a subphthalocyanine receptor material according to claim 1, wherein: when X is p-methoxyphenylthio, chlorinated phthalocyanin triacmide, p-methoxyphenylthiol, silver trifluoromethanesulfonate and triethylamine are mixed according to the molar ratio of 1: 1-20: 1-100, and the mixture is stirred and reacted for 1-30 hours in an organic solvent at the reflux temperature of the solvent to obtain the thiophenyl substituted phthalocyanin triacmide.
6. The method for synthesizing a subphthalocyanine receptor material according to claim 2, 3, 4 or 5, wherein the organic solvent is o-xylene, o-dichlorobenzene, p-xylene, m-xylene or mesitylene.
7. The subphthalocyanine receptor material of claim 1, which is applied to an active layer material in the field of bulk heterojunction organic solar cells.
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| CN109824709A (en) | 2019-05-31 |
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