CN112608333B - Micromolecules based on dithiadiazole carbazole derivatives, synthetic method thereof and application of micromolecules in organic photoelectric devices - Google Patents
Micromolecules based on dithiadiazole carbazole derivatives, synthetic method thereof and application of micromolecules in organic photoelectric devices Download PDFInfo
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Abstract
The invention discloses a bi-thiadiazole carbazole derivative-based small molecule, a synthesis method thereof and application of the bi-thiadiazole carbazole derivative-based small molecule in an organic photoelectric device. The material has strong absorption in the visible-near infrared region. DBTEh-4F, DBTEh-4Cl and DBTC8-4F, DBTC-4 Cl micromolecules are respectively used as electron acceptors and PBDB-T is used as donors to be mixed and used in an active layer of an organic solar cell, and the prepared device shows high photoelectric conversion efficiency. The small molecule receptors are simple to synthesize and have wide application prospect in the field of large-area low-cost organic solar cells.
Description
Technical Field
The invention relates to the field of organic photoelectric materials, in particular to micromolecules based on a dithiadiazole carbazole derivative, a synthetic method thereof and application in organic photoelectric devices.
Background
With the rapid development of society, the demand of human beings for energy is increasing. At present, energy supply mainly comes from fossil energy such as coal, petroleum and natural gas, but the energy storage is limited, and the energy is used in large quantities to cause serious environmental pollution, which is not in accordance with the policy guidelines of national energy conservation and emission reduction. To solve this problem, scientists are gradually looking at a new green renewable energy source, solar energy. Solar energy has become the largest energy source which can be developed and utilized in the world at present, is evaluated as an inexhaustible renewable resource, and is a novel clean and environment-friendly energy source. Organic/polymer solar cells have many advantages over inorganic solar cells, such as light weight, flexibility, large-area solution processing, low cost, etc., and thus have received much attention from researchers.
In recent years, organic solar cells have undergone a rapid development stage, innovative breakthroughs are made in material systems and device processes, and the device efficiency of single solar cells based on fullerene derivative receptor types is over 11%. However, fullerene derivatives have the defects of weak light absorption in a visible light region, narrow energy level regulation range, unstable photochemistry, poor morphology stability and the like, so that scientists have to search for receptor materials for replacing the fullerene derivatives. The non-fullerene fused ring small molecule receptor has received extensive attention and research because of its wide absorption spectrum, advantages such as electronic energy level that can be regulated and controlled. At present, the efficiency of the small molecule receptor based on Y6 exceeds 18%, but the synthesis cost of the fused ring material is high, and the fused ring material is not suitable for large-area commercial application. The advantages of the non-condensed ring non-fullerene receptor are equivalent to those of the condensed ring non-fullerene receptor in absorption and energy level, and in addition, the molecules are simple to synthesize, low in cost and excellent in stability, and have wide prospects in future commercial application.
Disclosure of Invention
The invention aims to design and synthesize a bi-thiadiazole carbazole derivative-based small molecule and the bi-thiadiazole carbazole derivative-based small molecule is used in an organic photoelectric device.
The invention relates to a bi-thiadiazole carbazole derivative-based micromolecule, which is characterized in that: the conjugated small molecule has the following structural general formula:
wherein R is 1 Is an alkyl chain; ar (Ar) 1 、Ar 2 Are the same or different conjugated aromatic condensed rings and derivative units; a. The 1 、A 2 Are the same or different electron withdrawing units.
Further, the bis-thiadiazole carbazole derivative-based small molecule is characterized in that: said R 1 Is C 1 ～C 60 A linear, branched or cyclic alkyl chain wherein one or more carbon atoms are substituted by oxygen atoms, alkenyl groups, alkynyl groups, aryl groups, hydroxyl groups, amino groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, methyl groups, ethyl groups, methoxy groups, nitro groups; or the hydrogen atom in the straight, branched or cyclic alkyl chain is substituted with a halogen atom or the above functional group.
Further, the bi-thiadiazole carbazole derivative-based small molecule is characterized in that: ar is 1 And Ar 2 The units are respectively selected from any one of the following structures:
wherein R is 2 、R 3 Is a hydrogen atom, a halogen atom or R 2 、R 3 Is selected from C 1 ～C 60 One or more carbon atoms on the alkyl chain or the alkyl group are substituted by more than one functional group of oxygen atom, sulfur atom, alkenyl, alkynyl, aryl or ester group, hydroxyl, amino, quaternary ammonium salt, phosphate radical, sulfonate radical and carboxyl; or the hydrogen atom in the straight, branched or cyclic alkyl chain is substituted with a halogen atom or the above functional group.
Further, the bi-thiadiazole carbazole derivative-based small molecule is characterized in that: a is described 1 And A 2 The units are respectively selected from any one of the following structures:
wherein X, Y is selected from hydrogen atom, halogen atom, C 1 ～C 60 Linear, branched or cyclic alkyl of (2), C 1 ～C 60 Alkoxy group of (1), C 1 ～C 60 Alkylthio, carbonyl, ester or cyano groups.
A synthetic method of a micromolecule based on a dithiadiazole carbazole derivative comprises the following steps: 1, still coupling; 2, vilsmeier-Haack reaction; and 3, performing knoevenagel condensation to obtain the micromolecule based on the dithiadiazole carbazole derivative.
Compared with the prior art, the invention has the following advantages:
1. the synthesized micromolecules based on the dithiadiazole carbazole derivatives have good solubility in common organic solvents such as dichloromethane, chloroform, tetrahydrofuran, toluene, chlorobenzene, dichlorobenzene and the like, and devices can be prepared by adopting a solution processing mode.
2. The synthesized micromolecules based on the dithiadiazole carbazole derivatives have strong absorption in a visible light-near infrared region, so that the solar spectrum can be fully utilized, and the photoelectric conversion efficiency is further improved.
3. The synthesized micromolecule based on the dithiadiazole carbazole derivative is simple to synthesize and low in cost, and is an ideal choice for preparing large-area commercial devices.
Drawings
FIG. 1 is a specific synthetic route for the compound DBTEh-4F prepared in example 5, the compound DBTEh-4Cl prepared in example 6, the compound DBTC8-4F prepared in example 7, and the compound DBTC8-4Cl prepared in example 8.
FIG. 2 shows UV-VIS absorption spectra of the compound DBTEh-4F prepared in example 5, the compound DBTEh-4Cl prepared in example 6, the compound DBTC8-4F prepared in example 7, and the compound DBTC8-4Cl prepared in example 8 in chloroform solution.
FIG. 3 shows UV-VIS absorption spectra of the compound DBTEh-4F prepared in example 5, the compound DBTEh-4Cl prepared in example 6, the compound DBTC8-4F prepared in example 7, and the compound DBTC8-4Cl prepared in example 8 in a thin film state.
FIG. 4 is a plot of Cyclic Voltammetry (CV) for the compound DBTEh-4F prepared in example 5, the compound DBTEh-4Cl prepared in example 6, the compound DBTC8-4F prepared in example 7, and the compound DBTC8-4Cl prepared in example 8.
FIG. 5 is a current-voltage (J-V) graph of an organic solar cell device prepared by matching PBDB-T using the compound DBTEh-4F prepared in example 5, the compound DBTEh-4Cl prepared in example 6, the compound DBTC8-4F prepared in example 7, and the compound DBTC8-4Cl prepared in example 8 as electron acceptors.
Detailed Description
The invention is further illustrated by the following specific examples, which are intended to facilitate a better understanding of the context of the invention, including in particular the synthesis, device preparation and characterization results, but which are not intended to limit the scope of the invention in any way.
The practice of the present invention may employ conventional techniques of chemical compound chemistry within the skill of the art. In the following examples, efforts are made to ensure accuracy with respect to numbers used (including amounts, temperature, reaction time, etc.) but some experimental errors and deviations should be accounted for. The temperatures used in the following examples are expressed in degrees Celsius and the pressures are at or near atmospheric. All solvents were purchased for analytical or chromatographic grade and all reactions were performed under an inert atmosphere of argon. All reagents were obtained commercially unless otherwise indicated.
Such as the synthetic route in figure 1.
Compound 1 was synthesized according to the method disclosed in (Polymer chemistry,2012,51 (3), 624-634.).
Compound 2 was synthesized according to the method disclosed (ACS Applied Materials & Interfaces 2020,12,16700-16706.).
Example 1: synthesis of Compound 3-1.
The reaction mixture was purified by dissolving compound 1 (2.15g, 3.5mmol), compound 2-1 (7.98g, 14.13mmol), pd (PPh) 3 ) 2 Cl 2 (2454mg, 0.35mmol), and then added to a 250ml two-necked flask, and after purging three times and filling with nitrogen, 60ml of anhydrous tetrahydrofuran was added, and the mixture was heated to 80 ℃ and stirred for 24 hours. After completion of the reaction, it was cooled to room temperature, extracted with dichloromethane, and washed with water three times. The organic phase was dried over anhydrous magnesium sulfate, the organic solvent was spin-dried, and the crude product was purified by column chromatography on silica gel to give a violet black solid 3-1 (3.29g, 75%). 1 H NMR(500MHz,CDCl 3 )δ8.23(d,J＝16.3Hz,2H),8.04(s,2H),7.22(d,J＝4.8Hz,2H),7.00(dd,J＝4.9,2.6Hz,2H),4.54(d,J＝7.3Hz,2H),2.28-2.19(m,1H),2.09-1.92(m,8H),1.55-1.38(m,10H),1.29(dd,J＝15.6,3.2Hz,12H),1.11-0.81(m,31H),0.80-0.72(m,12H),0.66(dt,J＝14.4,6.5Hz,18H). 13 CNMR(126MHz,CDCl 3 )δ157.75，157.34，149.65，149.55，139.39，137.72，137.08，135.85,124.24，124.12,122.55，121.47，110.02，109.36，52.90,47.65，43.26,39.57,34.23,32.05,31.87,29.63,28.68,27.52,27.36,26.92,26.85,25.28,23.02,22.81,22.62,14.12,14.09,10.82,10.66.HR-MS(MALDI-TOF)m/z calcd.for(C 76 H 101 N 5 O 2 S 6 ):1253.02.Found:1254.55.
Example 2: synthesis of Compound 3-2
3-2 Synthesis as above, the product was a purple black solid (3.50, 80%). 1 H NMR(500MHz,CDCl 3 )δ8.24(s,2H),8.00(s,2H),7.25(d,J＝4.8Hz,2H),7.01(d,J＝4.8Hz,2H),4.47(s,2H),2.26-2.13(m,2H),2.05-1.89(m,8H),1.54-1.35(m,10H),1.34-0.98(m,48H),0.89(t,J＝7.3Hz,5H),0.86-0.75(m,18H). 13 CNMR(126MHz,CDCl 3 )δ159.32，158.92,150.63,139.91,138.79,137.77,136.54,125.76,125.05,122.82,121.84,111.06,110.33,53.97,48.48,39.50,37.82,31.97,31.87,31.84,31.68,31.51,30.10,29.63,29.40,29.29,28.90,26.81,24.67,23.00,22.63,22.50,14.11,14.08.HR-MS(MALDI-TOF)m/z calcd.for(C 76 H 101 N 5 O 2 S 6 ):1253.02.Found:1254.55.
Example 3: synthesis of Compound 4-1.
1ml of phosphorus oxychloride was added to a 100ml two-necked reaction flask containing 5ml of DMF under ice-bath conditions, and stirred at room temperature for 30 minutes, and Compound 3-1 (0.71g, 0.56mmol) was dissolved in 20ml of dichloromethane, added to the above mixed solution, and stirred at 65 ℃ overnight. After the reaction was completed, it was cooled to room temperature, and a saturated sodium carbonate solution was added thereto, and stirred for 30 minutes, followed by extraction with dichloro, washing with water three times, drying with anhydrous sodium sulfate, removing the organic solvent by rotary evaporation under reduced pressure, and the mixed crude product was further purified by a silica gel column to obtain 4-1 (0.60g, 82%) as a violet-black solid compound. 1 H NMR(500MHz,CDCl 3 )δ9.88(s,2H),8.38-8.26(m,2H),8.12-8.06(m,2H),7.68-7.60(m,2H),4.65-4.49(m,3H),2.29-1.93(m,10H),1.47(d,J＝37.6Hz,15H),1.27(s,11H),1.10-0.93(m,30H),0.93-0.80(m,10H),0.76(t,J＝6.6Hz,10H),0.71-0.60(m,15H). 13 CNMR(126MHz,CDCl 3 )δ182.60,163.03,158.14,150.60,147.60,144.23,143.60,138.72,136.82,130.91,124.63,123.65,123.37,111.89,111.32,54.38,43.14,39.71,35.42,35.37,34.42,34.15,31.83,29.56,28.63,28.50,27.64,27.33,23.02,22.77,22.59,14.11,14.07,14.02,10.80,10.64.HR-MS(MALDI-TOF)m/z calcd.for(C 76 H 101 N 5 O 2 S 6 ):1309.04.Found:1309.57.
Example 4: synthesis of Compound 4-2.
Compound 4-2 was obtained in the same manner (0.62g, 85%). 1 H NMR(500MHz,CDCl 3 )δ9.88(s,2H),8.24(s,2H),8.00(s,2H),7.64(s,2H),4.50-4.40(m,2H),2.23-2.09(m,1H),2.02(t,J＝7.9Hz,8H),1.61(s,2H),1.56-1.36(m,10H),1.36-1.02(m,48H),0.90(t,J＝7.2Hz,5H),0.82(t,J＝6.7Hz,18H). 13 CNMR(126MHz,CDCl 3 )δ182.61,163.33,158.54,150.39,147.38,144.60,143.99,138.66,136.55,130.07,124.45,122.52,111.58,111.08,54.43,48.54,39.61,37.75,31.97,31.83,31.81,31.67,30.04,29.56,29.39,29.27,28.95,26.80,24.79,23.00,22.61,14.11,14.07.HR-MS(MALDI-TOF)m/z calcd.for(C 76 H 101 N 5 O 2 S 6 ):1309.04.Found:1309.57.
Example 5: and (3) synthesizing a conjugated small molecule DBTEh-4F.
Compound 4-1 (180mg, 0.137mmol), 5.6-difluoro-3- (dicyanomethylene) indolone (126mg, 0.55mmol) were charged in a 50mL two-necked flask, purged with nitrogen for 15 minutes, and then chloroform (20 mL) and 0.1mL pyridine were injected thereto, heated to 60 ℃ for reflux reaction for 12 hours. After the reaction solution was cooled to room temperature, ice water was added to quench the reaction, and the reaction solution was extracted with dichloromethane, concentrated and purified by column chromatography on silica gel (200 to 300 mesh) with dichloromethane as an eluent to give a black solid compound, DBTEh-4F (180mg, 76%). 1 H NMR(500MHz,CDCl 3 )δ 1 H NMR(500MHz,CDCl 3 )δ8.78(s,2H),8.34(s,2H),8.17(s,2H),7.92(s,2H),7.71(s,2H),7.59(s,2H),4.51(s,2H),2.15(s,10H),1.56-1.00(m,40H),0.95(dd,J＝12.5,6.8Hz,5H),0.89-0.64(m,36H). 13 CNMR(126MHz,CDCl 3 )δ185.78,166.25,159.92,158.85,158.10,155.31,155.21,153.23,153.11,151.39,150.35,150.16,148.08,139.40,138.76,138.31,136.37,134.34,124.33,114.77,114.66,114.57,112.32,112.18,112.09,67.71,54.25,48.80,43.34,39.90,35.55,34.35,34.13,31.87,31.84,29.59,28.49,27.44,26.99,22.99,22.91,22.63,14.14,14.09,10.64,10.54.HR-MS(MALDI-TOF)m/z calcd.for(C 100 H 105 F 4 N 9 O 2 S 6 ):1733.35.Found:1733.62.
Example 6 Synthesis of conjugated Small molecules DBTC 8-4F.
Compound 4-2 (180mg, 0.137mmol), 5.6-difluoro-3- (dicyanomethylene) indigoKetone (126mg, 0.55mmol) was charged in a 50mL two-necked flask, nitrogen gas was introduced for 15 minutes, and then 20mL of chloroform and 0.08mL of pyridine were injected thereto, heated to 60 ℃ and reacted under reflux for 12 hours. After the reaction solution was cooled to room temperature, ice water was added to quench the reaction, and the reaction solution was extracted with dichloromethane, concentrated, and purified by column chromatography on silica gel (200 to 300 mesh) with dichloromethane as an eluent to give BDTC8-4F as a black solid compound (165 mg, yield 69.6%). 1 H NMR(500MHz,CDCl 3 )δ 1 H NMR(500MHz,CDCl 3 )δ8.78(s,2H),8.34(s,2H),8.17(s,2H),7.92(s,2H),7.71(s,2H),7.59(s,2H), 1 H NMR(500MHz,CDCl 3 )δ 1 H NMR(500MHz,CDCl 3 )δ8.78(s,2H),8.34(s,2H),8.17(s,2H),7.92(s,2H),7.71(s,2H),7.59(s,2H),4.37(s,2H),2.16(s,10H),1.52-1.04(m,64H),0.95(t,J＝7.2Hz,5H),0.83(d,J＝13.9Hz,12H). 13 CNMR(126MHz,CDCl 3 )δ185.78,166.25,159.92,158.85,158.10,155.31,155.21,153.23,153.11,151.39,150.35,150.16,148.08,139.40,138.76,138.31,136.37,134.34,124.33,114.77,114.66,114.57,112.32,112.18,112.09,66.99,54.24,48.35,39.83,38.17,38.10,32.01,31.91,31.86,31.63,30.24,29.60,29.58,29.42,29.05,27.14,25.20,22.97,22.55,14.24,14.09.HR-MS(MALDI-TOF)m/z calcd.for(C 100 H 105 F 4 N 9 O 2 S 6 ):1733.35.Found:1733.65.
Example 7: and (3) synthesizing a conjugated small molecule DBTEh-4 Cl.
Compound 4-1 (180mg, 0.137mmol), 5.6-dichloro-3- (dicyanomethylene) indolone (146mg, 0.55mmol) were charged in a 50mL two-necked flask, purged with nitrogen for 15 minutes, and then 20mL of chloroform and 0.1mL of pyridine were injected thereto, heated to 60 ℃ and reacted under reflux for 12 hours. After the reaction solution was cooled to room temperature, ice water was added to quench the reaction, and the reaction solution was extracted with dichloromethane, concentrated and purified by column chromatography on silica gel (200 to 300 mesh) with dichloromethane as an eluent to give a black solid compound, DBTEh-4Cl (190mg, 77.2%). 1 H NMR(500MHz,CDCl 3 )δ8.76(s,2H),8.44(d,J＝9.7Hz,2H),8.12(s,2H),7.91(s,2H),7.79(d,J＝5.7Hz,2H),7.72(d,J＝12.9Hz,2H),4.49(s,2H),2.12(d,J＝46.1Hz,10H),1.54-0.90(m,51H),0.82(dt,J＝52.6,18.9Hz,30H). 13 CNMR(126MHz,CDCl 3 )δ185.50,166.27,160.04,159.90,159.57,157.58,150.26,149.92,148.39,139.83,139.04,138.65,138.36,135.78,126.41,126.37,124.44,124.30,124.22,118.89,114.74,114.48,111.91,112.18,112.09,67.44,54.14,48.72,43.40,39.97,35.53,34.28,34.18,32.20,32.09,29.58,29.14,28.49,27.44,27.32,22.99,22.63,14.14,14.09,10.64,10.54.HR-MS(MALDI-TOF)m/z calcd.for(C 100 H 105 C l4 N 9 O 2 S 6 ):1799.16.Found:1799.48.
Example 8: synthesis of conjugated micromolecule DBTC8-4Cl
Compound 4-2 (180mg, 0.137mmol), 5.6-dichloro-3- (dicyanomethylene) indolone (146mg, 0.55mmol) were charged in a 50mL two-necked flask, purged with nitrogen for 15 minutes, and then charged with 20mL of chloroform and 0.1mL of pyridine, heated to 60 ℃ for reflux reaction for 12 hours. And cooling the reaction liquid to room temperature, adding ice water to quench the reaction, extracting by using dichloromethane, concentrating, and carrying out silica gel (200-300 meshes) column chromatography for separation and purification, wherein the eluent is dichloromethane, so as to obtain a black solid compound DBTC8-4Cl (180mg, 73.2%). 1 H NMR(500MHz,CDCl 3 )δ8.68(s,2H),8.44(s,2H),8.05-7.42(m,6H),4.37(s,2H),2.16(s,10H),1.52-1.04(m,64H),0.95(t,J＝7.2Hz,5H),0.83(d,J＝13.9Hz,12H). 13 CNMR(126MHz,CDCl 3 )δ185.39,166.28,160.14,159.93,159.67,157.28,150.27,149.76,148.60,139.22,138.92,138.59,138.17,135.63,126.36,126.22,124.52,124.30,124.22,118.89,114.74,114.36,111.55,112.18,112.09,66.99,54.24,48.35,39.83,38.17,38.10,32.01,31.91,31.86,31.63,30.24,29.60,29.58,29.42,29.05,27.14,25.20,22.97,22.55,14.24,14.09.HR-MS(MALDI-TOF)m/z calcd.for(C 100 H 105 C l4 N 9 O 2 S 6 ):1799.16.Found:1799.48.
FIGS. 1 and 2 show the absorption spectra of the conjugated small molecules DBTEh-4F, DBTC-4F, DBTEh-4Cl and DBTC8-4Cl obtained in examples 5, 6, 7 and 8 in chloroform solution and thin film, respectively. The four small molecules all show stronger absorption in the 600-800nm region in chloroform solution. The four small molecules DBTEh-4F, DBTC8-4F, DBTEh-4CThe molar absorption coefficients of l, and DBTC8-4Cl in chloroform solution were 1.75X 10, respectively 5 M -1 cm -1 ，1.88×10 5 M -1 cm -1 ，1.95×10 5 M -1 cm -1 ，2.01×10 5 M -1 cm -1 . For thin film absorption, the thin film absorption of four small molecules is broadened, and the absorption peaks appear to be significantly red-shifted. The absorption edges of the four small molecules DBTEh-4F, DBTC-4F, DBTEh-4Cl and DBTC8-4Cl are 895nm,904nm,910nm and 926nm respectively, and the corresponding optical band gaps are 1.38eV,1.37eV,1.36eV and 1.34eV respectively. Through comparison, the conjugated small component with the chlorine atom at the end group has stronger absorption and narrower band gap in the near infrared region than the small molecule with the fluorine atom at the end group. The micromolecules with stronger absorption in the near infrared region are more beneficial to fully utilizing the sunlight in the near infrared region and obtaining higher short-circuit current.
FIG. 3 is a plot of Cyclic Voltammetry (CV) for the compound DBTEh-4F prepared in example 5, the compound DBTC8-4F prepared in example 6, the compound DBTEh-4Cl prepared in example 7, and the compound DBTC8-4Cl prepared in example 8. Hg/Hg 2 Cl 2 The electrode was corrected to 0.39V by Fc/Fc +. The HOMO/LUMO levels of the conjugated small molecules DBTEh-4F, DBTC-4F, DBTEh-4Cl and DBTC8-4Cl can be calculated to be-5.31/-3.80 eV, -5.39/-3.81eV, -5.36/-3.78eV, -5.41/-3.79eV, respectively. The appropriate HOMO/LUMO energy level facilitates better matching of the small molecule acceptor to the donor material for higher open circuit voltage and short circuit current.
Example 9
Representative small molecules synthesized in examples 1-8, DBTEh-4F, DBTC-4F, DBTEh-4Cl, and DBTC8-4Cl, were used as electron acceptors in organic solar cell devices (ITO anode/anode interface layer/active layer/cathode interface layer/cathode).
Respectively and sequentially ultrasonically cleaning the purchased Indium Tin Oxide (ITO) glass for 10 minutes by using acetone; ultrasonically cleaning the low-concentration micro detergent for 15 minutes; ultrasonic cleaning with ultrapure deionized water for 2-3 times, 10 minutes each time; ultrasonically cleaning chromatographic pure isopropanol for 10-15 min, and treating the cleaned ITO glass substrate with oxygen plasma for 5minZhong Daiyong. Spin-coating a layer of polyethylenedioxythiophene on the ITO substrate: polystyrene sulfonate (PEDOT: PSS), drying for 15min at 150 ℃, blending the micromolecules obtained in examples 5, 6, 7 and 8 with donor PBDB-T to prepare a chloroform solution, spin-coating a positive interface layer of the PEDOT: PSS as an active layer, spin-coating a layer of PFN-Br as a negative interface layer on the active layer, and vapor-plating Ag with the thickness of about 80nm as a negative electrode on the interface layer. The effective area of the battery is controlled by a mask plate and is 0.04cm 2 . All preparation processes were carried out in a nitrogen atmosphere glove box. The device performance test is carried out under the irradiation of an Oriel91192 AM 1.5G sunlight simulation lamp, and the radiation degree is 1kW/m 2 J-V curves were tested using a Keithley model 2400 digital Source Meter. The current-voltage curves of the prepared positive battery devices are shown in fig. 4 and 5, respectively, and the relevant data are listed in table one. The micromolecules can be used as electron acceptor materials to widen the spectral response range of the device, improve the short-circuit current of the battery device, have high filling factors, and have photoelectric conversion efficiency approaching 10% of the battery device prepared by blending DBTEh-4Cl and PBDB-T.
The device structure is as follows: ITO/PEDOT PSS/PBDB-T Acceptor/PFN-Br/Ag
The above examples of the present invention are merely examples for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (2)
1. Based on two thiadiazole carbazole derivative micromolecule, its characterized in that: the conjugated micromolecule has the following structural general formula:
said R 1 Is C 1 ～C 60 Straight chain of (1), C 1 ～C 60 Is branched or C 1 ～C 60 A cyclic alkyl chain of (a);
ar is 1 And Ar 2 The units are respectively selected from any one of the following structures:
wherein R is 2 、R 3 Is a hydrogen atom, a halogen atom or R 2 、R 3 Is selected from C 1 ～C 60 An alkyl chain of (a);
a is described 1 And A 2 The units are respectively selected from any one of the following structures:
wherein X, Y is selected from halogen atoms.
2. The use of the bis-thiadiazole carbazole derivative-based small molecule according to claim 1, wherein the bis-thiadiazole carbazole derivative-based small molecule is used as a donor and acceptor material in a photoactive layer of a solar cell or as an electron transport material in an optoelectronic device.
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