An organic optoelectronic compound, a preparation method thereof and an application thereof

Abstract

The present invention relates to an organic optoelectronic compound, characterized in that the general chemical structure formula of the organic optoelectronic compound is shown in Formula I: wherein, the value range of n is between 3 and 9; the present invention uses the oligomeric structure of benzodithiophene (BDT) as the central donor unit, and then uses fluorobenzotriazole as the acceptor unit to introduce a structure similar to oligomer on the microscopic molecules of small molecule optoelectronic materials, which not only makes up for the deficiency of the light absorption performance of small molecules, but also solves the defect of poor repeatability of polymers, that is, the organic optoelectronic compound contains the advantages of both macromolecular and small molecular organic optoelectronic compounds. This optoelectronic compound has a high photoelectric conversion efficiency as an oligomeric small molecule donor photovoltaic material and can be widely used in the optoelectronic field.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic optoelectronic materials, and particularly relates to an organic optoelectronic compound, a preparation method thereof, and an application thereof. Background Art

[0002] In the past few decades, solution-processed organic solar cells (OSCs) have been widely studied to produce renewable energy production devices with the advantages of semi-transparency, light weight, and flexibility. Generally, OSCs adopt a bulk heterojunction (BHJ) structure, using a conjugated polymer or a solution-processable p-type organic semiconductor as the donor and an n-type organic semiconductor as the electron acceptor. In recent years, high power conversion efficiency (PCE) exceeding 10% has been achieved by designing novel polymer donors.

[0003] Traditional organic solar cells can be divided into two categories: polymers and small molecules. Among them, polymer solar cells have the disadvantages of poor batch synthesis repeatability and difficult synthesis and preparation; small molecule solar cells have the disadvantages of low light absorption and poor thermal stability. These disadvantages make the unit power cost of organic solar cells relatively higher than other types of photovoltaic power generation technologies, restricting their practical applications.

[0004] Li Yongfang et al. synthesized two medium-bandgap p-type organic semiconductors H11 and H12 with a D-A structure as donors for non-fullerene OSCs using benzodithiophene (BDT) as the central donor unit, fluorobenzotriazole as the acceptor unit, and thiophene (H11) and non-thiophene (H12) conjugated side chains as acceptors, and used a low-bandgap n-type organic semiconductor IDIC as the acceptor (J. Am. Chem. Soc. 2017, 139, 5085 - 5094). Compared with H12 without a thiophene conjugated side chain, the two-dimensional conjugated small molecule H11 with a thiophene conjugated side chain showed stronger absorption, lower HOMO energy level, higher carrier mobility, and an ordered bimodal crystal arrangement in the blend film. These superior characteristics enabled the PCE to reach 9.73%.

[0005] This small molecule material enhanced the conjugated absorption of sunlight and improved the optoelectronic performance. However, compared with polymer materials, the performance is still poor, the repeatability is not good, and further conjugation strengthening and light absorption improvement are needed to enhance the optoelectronic performance.

[0006] Summary of the Invention

[0007] The first technical problem to be solved by the present invention is to provide an organic optoelectronic compound according to the above-mentioned prior art, which can not only make up for the insufficient light absorption performance of small molecule compounds, but also make up for the poor repeatability of polymers.

[0008] The second technical problem to be solved by the present invention is to provide a preparation method of the above-mentioned organic optoelectronic compound according to the above-mentioned prior art.

[0009] The third technical problem to be solved by the present invention is to provide an application of the above-mentioned organic optoelectronic compound according to the above-mentioned prior art.

[0010] The technical solution adopted by the present invention to solve the above first technical problem is as follows: an organic optoelectronic compound, characterized in that the general chemical structure formula of the organic optoelectronic compound is shown in Formula I:

[0011]

[0012] Among them, the value range of n is between 3 and 9;

[0013] A is one of the following unit structures:

[0014]

[0015]

[0016] X1, X2, X3, X4, X5, X6 are all H or F;

[0017] Z is O or S;

[0018] R1 is any one of H, hydrocarbon group, thiol group, thienylthiol group; R2 is any one of H, hydrocarbon group, thiol group.

[0019] Preferably, for the above R1 and R2, the hydrocarbon group is any one of straight-chain, branched-chain, and cycloalkyl groups with C1-C30.

[0020] Preferably, the chemical structural formula of the organic optoelectronic compound is shown in Formula II:

[0021]

[0022] Among them, R1 is any one of H, hydrocarbon group, thiol group, thienylthiol group; R2 is any one of H, hydrocarbon group, thiol group.

[0023] Preferably, the chemical structural formula of the organic optoelectronic compound is shown in Formula III:

[0024]

[0025] Preferably, the chemical structural formula of the organic optoelectronic compound is as shown in Formula VII or Formula VIII:

[0026]

[0027]

[0028] The technical solution adopted by the present invention to solve the above-mentioned second technical problem is: a preparation method of the above-mentioned organic optoelectronic compound, characterized in that: in an inert gas atmosphere, a bis(trimethyltin) end group compound and a halogenated end group compound are subjected to a Stille coupling reaction to obtain the organic optoelectronic compound;

[0029] Among them, the chemical structural formula of the bis(trimethyltin) end group compound is as shown in the formula:

[0030]

[0031] The chemical structural formula of the halogenated end group compound is as shown in Formula V:

[0032]

[0033] Y is any one of Br, Cl, and I;

[0034] X1, X2, X3, X4, X5, and X6 are all H or F;

[0035] Z is O or S;

[0036] R1 is any one of H, hydrocarbon group, thiol group, and thiophenethiol group; R2 is any one of H, hydrocarbon group, and thiol group.

[0037] In order to reduce reaction by-products, preferably, the reaction temperature of the reactant bis(trimethyltin) end group compound and the reactant halogenated end group compound is 100°C to 140°C, the reaction solvent is a toluene-based solvent, the reaction time is 12h to 20h, the molar ratio of the reactant bis(trimethyltin) end group compound to the reactant halogenated end group compound is 1:(2 to 2.4), and the ratio of the total amount of the two reactants to the reaction solvent is 10 ml / mmol to 90 ml / mmol.

[0038] In order to promote and ensure the reaction rate of the two reactants, a catalyst Pd(PPh3)4 or Pd(O2CCH3)2 or Pd(O2CCH3)2(PPh3)2 or PdCl2(PPh3)2 is added during the reaction of the reactant bis(trimethyltin) end group compound and the reactant halogenated end group compound, and the molar ratio of the catalyst to the bis(trimethyltin) end group compound is (10 to 30):100°C.

[0039] The technical solution adopted by the present invention to solve the above-mentioned third technical problem is as follows: an application of the above-mentioned optoelectromechanical compound in optoelectronic devices.

[0040] In the above solution, the optoelectronic device is a field effect transistor, an organic light emitting diode or a solar cell.

[0041] Compared with the prior art, the advantages of the present invention are as follows: 1. The present invention uses the oligomeric structure of benzodithiophene (BDT) as the central donor unit, and then uses fluorobenzotriazole as the acceptor unit to introduce a structure similar to oligomer on the microscopic molecules of small molecule optoelectronic materials, which not only makes up for the deficiency of the light absorption performance of small molecules, but also solves the defect of poor reproducibility of polymers, that is, the organic optoelectronic compound contains the advantages of both macromolecular and small molecular organic optoelectronic compounds. This optoelectronic compound has a high photoelectric conversion efficiency as an oligomeric small molecule donor photovoltaic material and can be widely used in the optoelectronic field; 2. The synthesis steps of the organic optoelectronic compound of the present invention are simple, easy to purify, and the structure is determined. Description of the Drawings

[0042] Figure 1 1H spectrum of the compound shown in Formula III;

[0043] Figure 2 13C spectrum of the compound shown in Formula III;

[0044] Figure 3 IR spectrum of the compound shown in Formula III;

[0045] Figure 4 Thermal flow-temperature curve of the compound shown in Formula III;

[0046] Figure 5 UV-Vis absorption spectrum of the compound shown in Formula III obtained in solution (THF);

[0047] Figure 6 Cyclic voltammogram of the compound shown in Formula III;

[0048] Figure 7 Current density-voltage curve of the compound shown in Formula III;

[0049] Figure 8 1H spectrum of the compound shown in Formula VII;

[0050] Figure 9 13C spectrum of the compound shown in Formula VII;

[0051] Figure 10 Thermal flow-temperature curve of the compound shown in Formula VII;

[0052] Figure 11The ultraviolet-visible absorption spectrum of the compound shown in Formula VII obtained in a solution (THF);

[0053] Figure 12 The cyclic voltammogram of the compound shown in Formula VII;

[0054] Figure 13 The 1H NMR spectrum of the compound shown in Formula VIII;

[0055] Figure 14 The 13C NMR spectrum of the compound shown in Formula VIII;

[0056] Figure 15 The heat flow-temperature curve of the compound shown in Formula VIII;

[0057] Figure 16 The ultraviolet-visible absorption spectrum of the compound shown in Formula VIII obtained in a solution (THF);

[0058] Figure 17 The cyclic voltammogram of the compound shown in Formula VIII. Detailed implementation manners

[0059] The present invention will be further described in detail below with reference to the accompanying drawings and embodiments.

[0060] The general chemical structure formula of the organic optoelectronic compound of the present invention is shown in Formula I:

[0061]

[0062] Among them, the value range of n is between 3 and 9;

[0063] A is one of the following unit structures:

[0064]

[0065]

[0066] X1, X2, X3, X4, X5, and X6 are all H or F;

[0067] Z is O or S;

[0068] R1 is any one of H, hydrocarbon group, thiol group, and thienylthiol group; R2 is any one of H, hydrocarbon group, and thiol group.

[0069] The preparation method of the organic optoelectronic compound is as follows: in an inert gas atmosphere, the reactant bis(trimethyltin) end group compound and the reactant halogenated end group compound are subjected to a Stille coupling reaction to obtain the organic optoelectronic compound;

[0070] Specifically, the reaction temperature of the reactant bis(trimethyltin) end-group compound and the reactant halogenated end-group compound is 100°C to 140°C, the reaction solvent is o-xylene or m-xylene or p-xylene or toluene, and the reaction time is 12h to 20h.

[0071] The molar ratio of the reactant bis(trimethyltin) end-group compound to the reactant halogenated end-group compound is 1:(2 to 2.4), and the ratio of the total amount of the two reactants to the reaction solvent is 10 ml / mmol to 90 ml / mmol.

[0072] During the reaction of the reactant bis(trimethyltin) end-group compound and the reactant halogenated end-group compound, a catalyst Pd(PPh3)4 or Pd(O2CCH3)2 or Pd(O2CCH3)2(PPh3)2 or PdCl2(PPh3)2 is also added, and the molar ratio of the catalyst to the bis(trimethyltin) end-group compound is (10 to 30):100.

[0073] Among them, the chemical structural formula of the bis(trimethyltin) end-group compound is as shown in Formula IV:

[0074]

[0075] The chemical structural formula of the halogenated end-group compound is as shown in Formula V:

[0076]

[0077] Y is any one of Br, Cl, and I;

[0078] X1, X2, X3, X4, X5, and X6 are all H or F;

[0079] Z is O or S;

[0080] R1 is any one of H, a hydrocarbon group, a thiol group, and a thiophene thiol group; R2 is any one of H, a hydrocarbon group, and a thiol group.

[0081] The following is elaborated in combination with specific embodiments:

[0082] Example 1

[0083] The general structural formula of the organic optoelectronic compound in this example is as shown in Formula III:

[0084]

[0085] n = 3, and this organic optoelectronic compound is a black solid powder with a metallic luster.

[0086] The preparation method of this organic optoelectronic compound is as follows:

[0087] The bis(trimethyltin) end group compound used in this example is: (4,8-bis(5-((2-ethylhexyl)thio)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl)bis(trimethylstannane); (purchased from Shanghai Bide Pharmaceutical Technology Co., Ltd.);

[0088] (4,8-bis(5-((2-ethylhexyl)thio)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl)bis(trimethylstannane)

[0089] The halogenated end group compound used in this example is: 2-ethylhexyl (E)-3-(5-(7-(5-bromothiophen-2-yl)-5,6-difluoro-2-(2-hexyldecyl)-2H-benzo[d][1,2,3]triazol-4-yl)thiophen-2-yl)-2-cyanoacrylate) (purchased from Shenzhen Ruixun Optoelectronic Materials Technology Co., Ltd.);

[0090] (2-ethylhexyl (E)-3-(5-(7-(5-bromothiophen-2-yl)-5,6-difluoro-2-(2-hexyldecyl)-2H-benzo[d][1,2,3]triazol-4-yl)thiophen-2-yl)-2-cyanoacrylate).

[0091] Dissolve 237 mg (0.22 mmol) of the above bis(trimethyltin) end group compound and 365 mg (0.44 mmol) of the above halogenated end group compound in 20 ml of xylene; after purging with argon for 5 min, add 25 mg (0.022 mmol) of the catalyst Pd(PPh3)4. Then purge the mixture with nitrogen for 15 minutes, and then stir the reaction mixture under a nitrogen atmosphere at 100 °C for 12 h. After cooling to room temperature, pour the reaction mixture into water and use dichloromethane (the volume ratio of dichloromethane to water is 1:1) as the eluent, and purify by silica gel column chromatography to obtain a dark solid with a yield of 56%. NMR testing proves it to be the desired organic optoelectronic compound.

[0092] Perform the following operations on the organic optoelectronic compound prepared in this example:

[0093] I. Perform the following performance tests on the organic optoelectronic compound prepared in this example:

[0094] NMR analysis: The 1H spectrum and 13C spectrum obtained by NMR testing of the organic optoelectronic compound prepared in this example are as Figure 1 、 Figure 2As shown, according to the spectrum, it can be determined that its structure is correct.

[0095] IR test: The organic optoelectronic compound of this example was subjected to IR testing as Figure 3 shown.

[0096] Thermal stability test: The organic optoelectronic compound of this example was placed in a differential scanning calorimeter, and the change in heat flow was measured during heating, as Figure 4 shown. Before the temperature reached 220 °C, there was no change in heat flow, indicating that the compound would not undergo a phase change due to overheating at normal operating temperatures and had high thermal stability.

[0097] Absorption spectrum test: The absorption spectra of the organic optoelectronic compound prepared in this example in chloroform solution and thin film were measured using ultraviolet-visible light absorption and are shown in Figure 5 respectively. The maximum absorption peak was at 463 nm, and the calculated optical band gap Eg was 2.67 eV.

[0098] Electrochemical test: The organic optoelectronic compound prepared in this example was measured by cyclic voltammetry. An acetonitrile solution of 0.1 mol / L tetrabutylammonium hexafluorophosphate was used as the electrolyte; a platinum wire was used as the counter electrode; and a silver wire was used as the reference electrode. The cyclic voltammogram shown in Figure 6 was measured. By calculation, the highest occupied molecular orbital (HOMO) energy level was -6.53 eV, and the lowest unoccupied molecular orbital (LUMO) energy level was -3.99 eV.

[0099] II. Preparation of a solar cell using the organic optoelectronic compound prepared in this example:

[0100] The organic optoelectronic compound prepared in this example and the compound IDIC shown in the following formula VI (purchased from Shanghai Bide Pharmaceutical Technology Co., Ltd.) were dissolved in 160 μl of chloroform at a molar ratio of 2:1 to form a 12 mg / ml solution.

[0101]

[0102] Poly(3,4-ethylenedioxythiophene): polystyrene sulfonate (PEDOT∶PSS) (both purchased from Merck Chemical Technology (Shanghai) Co., Ltd.) was prepared in a mass ratio of 1:3, and then coated on the surface of a glass substrate covered with indium tin oxide (ITO) (purchased from Merck Chemical Technology (Shanghai) Co., Ltd.) to form a base layer. A solution prepared from the above-mentioned organic optoelectronic compound and the compound shown in Formula VI was spin-coated on the surface of the base layer in a glove box filled with nitrogen to prepare an active layer, and then annealed at 110 °C for 10 minutes. Then, a methanol solution of amino N-oxide layer-functionalized perylene diimide (PDINO) with a concentration of 1.0 mol / mL (purchased from Shenzhen Ruixun Optoelectronic Materials Technology Co., Ltd.) was deposited on the top of the active layer as a cathode buffer layer. Finally, 100 nm thick aluminum was vacuum-evaporated onto the cathode buffer layer as an electrode under a pressure of about 5×10 -6 mbar.

[0103] The above-prepared organic solar cell was used with a solar simulator as the light source, and its performance was tested under the standard solar spectrum AM1.5G and standard illumination intensity. By adjusting the parameters, the optimal data were obtained as shown Figure 7 . The open-circuit voltage was 0.98 V, the short-circuit current was 16.55 mA / cm 2 , the fill factor was 78.15%, and the energy conversion efficiency was 12.6%.

[0104] Example 2

[0105] The structural general formula of the organic optoelectronic compound in this example is:

[0106]

[0107] n = 6, and the organic optoelectronic compound is a yellow solid powder.

[0108] The preparation method of the organic optoelectronic compound is as follows:

[0109] The bis(trimethyltin) end-group compound used in this example is: (4,4′,4″,4″′,4″″,4″′″,8,8′,8″,8″′,8″″,8″″′-dodecyl(5-((2-ethylhexyl)thio)thiophen-2-yl)-[2,2′:6′,2″:6″,2″′:6″′,2″″:6″″,2″″′-hexabenz[1,2-b:4,5-b′-dithiophene]-6,6″″′-diyl]bis(trimethylstannane) (purchased from Shanghai Bide Pharmaceutical Technology Co., Ltd.);

[0110] (4,4′,4″,4″′,4″″,4″″′,8,8′,8″,8″′,8″″,8″″′-dodecakis(5-((2-ethylhexyl)thio)thiophen-2-yl)-[2,2′:6′,2″:6″,2″′:6″′,2″″:6″″,2″″′-sexibenzo[1,2-b:4,5-b′]dithiophene]-6,6″″′-diyl)bis(trimethylstannane).

[0111] The halogenated end group compound used in this example is: 4-(5-bromothiophen-2-yl)-5,6-difluoro-2-(2-hexyldecyl)-7-(5-(2-hexyldecyl)-[2,2-bithiophene]-5-yl)-2H-benzo[d][1,2,3]triazole (purchased from Shenzhen Ruixun Optoelectronic Materials Technology Co., Ltd.);

[0112] 4-(5-bromothiophen-2-yl)-5,6-difluoro-2-(2-hexyldecyl)-7-(5′-(2-hexyldecyl)-[2,2′-bithiophen]-5-yl)-2H-benzo[d][1,2,3]triazole.

[0113] Dissolve 417 mg (0.10 mmol) of the above bis(trimethyltin) end group compound and 222 mg (0.24 mmol) of the above halogenated end group compound in 50 ml of toluene; after purging with argon for 5 min, add 14 mg (0.02 mmol) of the catalyst PdCl2(PPh3)2. Then purge the mixture with nitrogen for 15 minutes, and then stir the reaction mixture under a nitrogen atmosphere at 120 °C for 16 h. After cooling to room temperature, pour the reaction mixture into water and use dichloromethane (the volume ratio of dichloromethane to water is 1:1) as the eluent, and purify it by silica gel column chromatography to obtain a dark solid with a yield of 60%. The nuclear magnetic resonance proves that it is the required organic optoelectronic compound.

[0114] Perform the following operations on the organic optoelectronic compound prepared in this example:

[0115] I. Perform the following performance tests on the organic optoelectronic compound prepared in this example:

[0116] Nuclear magnetic resonance analysis: The 1H spectrum and 13C spectrum obtained by nuclear magnetic resonance testing of the organic optoelectronic compound prepared in this example are as shown in Figure 8 、 Figure 9 shown. According to the spectra, it can be determined that its structure is correct;

[0117] Thermal stability test: The organic optoelectronic compound prepared in this example was placed in a thermogravimetric analyzer, and the weight change was measured by heating. As Figure 10 shown, the weight loss was less than 5% before the temperature reached 179 °C, indicating that the compound would not degrade due to overheating at the normal operating temperature and had high thermal stability.

[0118] Absorption spectrum test: The absorption spectra of the organic optoelectronic compound prepared in this example measured by ultraviolet-visible light absorption in chloroform solution and thin film are shown in Figure 11 respectively. The maximum absorption peak was at 436 nm, and the calculated optical band gap Eg was 2.83 eV.

[0119] Electrochemical test: The organic optoelectronic compound prepared in this example was measured by cyclic voltammetry. An acetonitrile solution of 0.1 mol / L tetrabutylammonium hexafluorophosphate was used as the electrolyte; a platinum wire was used as the counter electrode; a silver wire was used as the reference electrode. The cyclic voltammogram shown in Figure 12 was measured. By calculation, the highest occupied molecular orbital (HOMO) energy level was -5.53 eV, and the lowest unoccupied molecular orbital (LUMO) energy level was -3.64 eV.

[0120] II. Preparation of a solar cell using the organic optoelectronic compound prepared in this example:

[0121] The organic optoelectronic compound prepared in this example and the compound IDIC shown in the following formula VI (purchased from Shanghai Bide Pharmaceutical Technology Co., Ltd.) were dissolved in 160 μl of chloroform at a molar ratio of 2:1 to prepare a 12 mg / ml solution.

[0122]

[0123] Poly(3,4-ethylenedioxythiophene):polystyrene sulfonate (PEDOT:PSS) (both purchased from Merck Chemical Technology (Shanghai) Co., Ltd.) was prepared at a mass ratio of 1:3, and then coated on the surface of an indium tin oxide (ITO) (purchased from Merck Chemical Technology (Shanghai) Co., Ltd.) covered glass substrate to form a base layer. The solution prepared from the above organic optoelectronic compound and the compound shown in formula VI was spin-coated on the surface of the base layer in a glove box filled with nitrogen to prepare an active layer, and then annealed at 110 °C for 10 minutes. Then, a methanol solution of perylene diimide (PDINO) functionalized with an amino N-oxide layer at a concentration of 1.0 mol / mL (purchased from Shenzhen Ruixun Optoelectronic Materials Technology Co., Ltd.) was deposited on the top of the active layer as a cathode buffer layer. Finally, 100 nm thick aluminum was vacuum-evaporated onto the cathode buffer layer at a pressure of about 5×10 -6 mbar as the electrode.

[0124] Performance testing was carried out on the above-prepared solar simulator for organic solar cells as the light source. By adjusting the parameters, the open-circuit voltage was obtained as 0.89 V, and the short-circuit current was 17.43 mA / cm 2 , the fill factor was 80.02%, and the energy conversion efficiency was 12.41%.

[0125] Example 3

[0126] The structural general formula of the organic optoelectronic compound in this example is shown in Formula VIII:

[0127]

[0128] n = 9, and this organic optoelectronic compound is a black solid.

[0129] The preparation method of this organic optoelectronic compound is as follows:

[0130] The bis(trimethylstannyl) end group compound used in this example is: ((4,4′,4″,4″′,4″″,4″″′,4″″″,4″″″′,4″″″″,8,8′,8″,8″′,8″″,8″″′,8″″″,8″″″′,8″″″″-octadecakis(5-((2-ethylhexyl)thio)thiophen-2-yl)-[2,2′:6′,2″:6″,2″′:6″′,2″″:6″″,2″″′:6″″′,2″″″:6″″″,2″″″′:6″″″′,2″″″″-novibenzo[1,2-b:4,5-b′-]dithiophene]-6,6″′″′″-diyl)bis(trimethylstannane) (purchased from Shanghai Bide Pharmaceutical Technology Co., Ltd.)

[0131] ((4,4′,4″,4″′,4″″,4″″′,4″″″,4″″″′,4″″″″,8,8′,8″,8″′,8″″,8″″′,8″″″,8″″″′,8″″″″-octadecakis(5-((2-ethylhexyl)thio)thiophen-2-yl)-[2,2′:6′,2″:6″,2″′:6″′,2″″:6″″,2″″′:6″″′,2″″″:6″″″,2″″″′:6″″″′,2″″″″-novibenzo[1,2-b:4,5-b′]dithiophene]-6,6″″″″-diyl)bis(trimethylstannane)

[0132] The halogenated end group compound used in this example is: 2-ethylhexyl (E)-3-(5-(7-(5-bromothiophen-2-yl)-2-(2-hexyldecyl)-2H-benzo[d][1,2,3]triazol-4-yl)thiophen-2-yl)-2-cyanoacrylate (purchased from Shenzhen Ruixun Optoelectronic Materials Technology Co., Ltd.)

[0133] 2-ethylhexyl (E)-3-(5-(7-(5-bromothiophen-2-yl)-2-(2-hexyldecyl)-2H-benzo[d][1,2,3]triazol-4-yl)thiophen-2-yl)-2-cyanoacrylate.

[0134] Dissolve 609 mg (0.10 mmol) of the above-mentioned bis(trimethyltin) end group compound and 154 mg (0.22 mmol) (1:2.2) of the above-mentioned halogenated end group compound in 90 ml of toluene; after purging with argon for 5 min, add 40 mg of the catalyst Pd(O2CCH3)2. Then purge the mixture with nitrogen for 15 minutes, and then stir the reaction mixture under a nitrogen atmosphere at 140 °C for 20 h. After cooling to room temperature, pour the reaction mixture into water for extraction. After drying, use petroleum ether as the eluent and purify by silica gel column chromatography to obtain a black solid, which is the organic optoelectronic compound with a yield of 70%.

[0135] Perform the following operations on the organic optoelectronic compound prepared in this example:

[0136] I. Perform the following performance tests on the organic optoelectronic compound prepared in this example:

[0137] NMR analysis: The 1H spectrum and 13C spectrum obtained from the NMR test of the organic optoelectronic compound prepared in this example are as shown in Figure 13 、 Figure 14 . According to the spectra, its structure can be determined to be correct;

[0138] Thermal stability test: Place the organic optoelectronic compound prepared in this example in a thermogravimetric analyzer. When heated, a weight change occurs. As shown in Figure 15 , the weight loss is 10% at a temperature of 157.7 °C, indicating that the compound will not undergo a phase change due to overheating at the normal use temperature and has good thermal stability.

[0139] Absorption spectrum test: The absorption spectra of the organic optoelectronic compound prepared in this example measured by ultraviolet-visible light absorption in a tetrahydrofuran solution are shown in Figure 16 respectively. The maximum absorption peak is at 434 nm, and the calculated optical band gap Eg is 2.84 eV.

[0140] Electrochemical test: The organic optoelectronic compound prepared in this example was determined by cyclic voltammetry. An acetonitrile solution of 0.1 mol / L tetrabutylammonium hexafluorophosphate was used as the electrolyte; a platinum wire was used as the counter electrode; and a silver wire was used as the reference electrode. The cyclic voltammogram curve as shown in Figure 17 was measured. By calculation, the highest occupied molecular orbital (HOMO) energy level was -5.53 eV, and the lowest unoccupied molecular orbital (LUMO) energy level was -3.49 eV.

[0141] II. Preparation of a solar cell using the organic optoelectronic compound prepared in this example:

[0142] The organic optoelectronic compound prepared in this example and the compound IDIC shown in the following formula VI (purchased from Shanghai Bide Pharmatech Co., Ltd.) were dissolved in 160 μl of chloroform at a molar ratio of 2:1 to form a 12 mg / ml solution.

[0143]

[0144] Poly(3,4-ethylenedioxythiophene):polystyrene sulfonate (PEDOT:PSS) (both purchased from Merck Chemical Technology (Shanghai) Co., Ltd.) was prepared according to a mass ratio of 1:3, and then coated on the surface of a glass substrate covered with indium tin oxide (ITO) (purchased from Merck Chemical Technology (Shanghai) Co., Ltd.) to form a base layer. The solution prepared from the above organic optoelectronic compound and the compound shown in formula VI was spin-coated on the surface of the base layer in a glove box filled with nitrogen to prepare an active layer, and then annealed at 110 °C for 10 minutes. Then, a methanol solution of perylene diimide functionalized with amino N-oxide layer (PDINO) (purchased from Shenzhen Ruixun Optoelectronic Materials Technology Co., Ltd.) with a concentration of 1.0 mol / mL was deposited on the top of the active layer as the cathode buffer layer. Finally, 100 nm thick aluminum was vacuum-evaporated onto the cathode buffer layer at a pressure of about 5×10 -6 mbar as the electrode.

Claims

1. An organic optoelectronic compound, characterized in that: The chemical structural formula of the organic optoelectronic compound is shown in Formula II: Formula II Wherein, R1 is a hydrocarbon group; R2 is a hydrocarbon group; the value range of n is between 3 and 9.

2. The organic optoelectronic compound according to claim 1, wherein: The chemical structural formula of the organic optoelectronic compound is shown in Formula III: Formula III.

3. An organic optoelectronic compound, characterized in that: The chemical structural formula of the organic optoelectronic compound is shown in Formula VII or Formula VIII: Formula VII Formula VIII; Wherein, the value range of n is between 3 and 9.

4. Application of the organic optoelectronic compound according to any one of claims 1 to 3 in an optoelectronic device.

5. The application according to claim 4, wherein: The optoelectronic device is a field effect transistor, an organic light emitting diode or a solar cell.

Images