CN114181242B - Silane-substituted aromatic fused ring compound and preparation method and application thereof - Google Patents

Silane-substituted aromatic fused ring compound and preparation method and application thereof Download PDF

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CN114181242B
CN114181242B CN202111441261.3A CN202111441261A CN114181242B CN 114181242 B CN114181242 B CN 114181242B CN 202111441261 A CN202111441261 A CN 202111441261A CN 114181242 B CN114181242 B CN 114181242B
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邵明
张迪
王振业
徐美辰
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Huazhong University of Science and Technology
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Abstract

The invention belongs to the technical field of organic photovoltaics, and in particular relates to a silane-substituted aromatic fused ring compound, a preparation method and application thereof, wherein the preparation method comprises the following steps: the silane group substituted aromatic condensed ring organic small molecule acceptor material with excellent solubility is obtained by introducing a silane group chain into a side chain structure of an organic small molecule, and can be used in an optoelectronic device to realize higher energy conversion efficiency and good intrinsic flexibility and tensile mechanical property. When the organic micromolecule based on the silane-substituted aromatic condensed ring is used as a non-fullerene organic electronic acceptor material, the organic micromolecule is applied to an organic solar cell to obtain high energy conversion efficiency; meanwhile, it shows good intrinsic flexibility and tensile mechanical properties during external stress stretching.

Description

Silane-substituted aromatic fused ring compound and preparation method and application thereof
Technical Field
The invention belongs to the technical field of organic photovoltaics, and particularly relates to a silane-substituted aromatic fused ring compound, and a preparation method and application thereof.
Background
The organic solar cell is expected to become next-generation high-efficiency wearable power generation equipment because of the advantages of low preparation cost, solution processing, light weight, flexibility, realization of large-area roll-to-roll production and the like, and is concerned by more and more scientific researchers. In recent years, with the intensive research of researchers, especially with the continuous search of active layer materials, preparation processes, device structures and the like, the performance of organic solar cells is continuously improved, the power conversion efficiency is continuously refreshed, and the device efficiency based on n-type small molecule acceptor materials and p-type polymer donor materials is over 19 percent up to now. However, the mechanical properties such as mechanical properties and tensile properties of the organic solar cells cannot meet the basic requirements of practical portable wearable power generation equipment.
Disclosure of Invention
Aiming at the defects and improvement demands of the prior art, the invention provides a silane-group-substituted aromatic condensed-cyclic compound, a preparation method and application thereof, and aims to provide an organic electron acceptor material which can be applied to stretchable wearable electronic equipment and has high energy conversion efficiency.
In order to achieve the above object, according to one aspect of the present invention, there is provided a silyl-substituted aromatic condensed-ring compound represented by the following formula i:
Figure BDA0003383435960000021
wherein R is 1 ,R 2 Respectively is any one of alkyl, alkoxy, silane and substituted aromatic ring, wherein the alkyl is one of straight chain or branched chain alkyl with 1-30 carbon atoms; the alkoxy is one of straight-chain or branched-chain alkoxy with 1-30 carbon atoms; the silane group is one of straight-chain or branched-chain silane groups with 3-30 carbon atoms; the substituted aromatic ring is one of thiophene, benzothiophene, benzene ring and selenophene with C6-20 alkyl and/or C1-30 alkoxy;
R 3 ,R 4 ,R 5 the alkyl is one of straight-chain or branched-chain alkyl with 1-30 carbon atoms; the alkoxy is one of straight-chain or branched-chain alkoxy with 1-30 carbon atoms; the conjugated aromatic ring is one of thiophene, benzothiophene, benzene ring, furan and selenophene; the substituted aromatic ring is one of thiophene, thiofuran, benzene ring, furan and selenophene with alkyl with 1-30 carbon atoms and/or alkoxy with 1-30 carbon atoms.
The invention also provides a synthesis method of the silicane substituted aromatic condensed ring compound, which comprises the following steps: the compound A and the compound B are subjected to electrophilic substitution reaction to obtain the silane group substituted aromatic condensed ring compound;
Figure BDA0003383435960000022
further, the conditions of the electrophilic substitution reaction are: n, N-dimethylformamide is taken as a solvent, potassium iodide and potassium carbonate are added, the mol ratio of the compound A to the compound B is 1:6-8, and the reaction is carried out for 12-48 hours at the temperature of 105-115 ℃.
The invention also provides an organic small molecule based on the silyl substituted aromatic condensed ring structure, which has the following structure:
Figure BDA0003383435960000031
wherein R is 1 ,R 2 Respectively is any one of alkyl, alkoxy, silane and substituted aromatic ring, wherein the alkyl is one of straight chain or branched chain alkyl with 1-30 carbon atoms; the alkoxy is one of straight-chain or branched-chain alkoxy with 1-30 carbon atoms; the silane group is one of straight-chain or branched-chain silane groups with 3-30 carbon atoms; the substituted aromatic ring is one of thiophene, benzothiophene, benzene ring and selenophene with C6-20 alkyl and/or C1-30 alkoxy;
R 3 ,R 4 ,R 5 the alkyl is one of straight-chain or branched-chain alkyl with 1-30 carbon atoms; the alkoxy is one of straight-chain or branched-chain alkoxy with 1-30 carbon atoms; the conjugated aromatic ring is one of thiophene, benzothiophene, benzene ring, furan and selenophene; the substituted aromatic ring is one of thiophene, benzothiophene, benzene ring, furan and selenophene with alkyl with 1-30 carbon atoms and/or alkoxy with 1-30 carbon atoms; ar is a group of formula II:
Figure BDA0003383435960000032
in the formula II, EG represents an electron withdrawing group, and specifically any one of the following structures:
Figure BDA0003383435960000041
wherein each R in the above EG structure 6 Each independently is selected from one of hydrogen atom, alkyl, cycloalkyl, alkoxy, alkylthio, ester group, carbonyl, halogen substituent, aralkyl and heteroalkyl, wherein the alkyl, the alkoxy, the alkylthio, the aralkyl and the heteroalkyl are each one of straight-chain or branched-chain alkyl with 1-30 carbon atoms, and the cycloalkyl is one of cycloalkyl with 3-30 carbon atoms.
The invention also provides a synthesis method of the organic small molecule, which comprises the following steps:
s1, reacting a compound shown in the formula I with phosphorus oxychloride and N, N-dimethylformamide to obtain a compound C through Vilsmeier-Haack reaction;
s2, carrying out Knoevenagel condensation reaction on the compound C and EG as described above to obtain the small organic molecule shown in the formula I';
wherein, the compound C has the following structure:
Figure BDA0003383435960000051
further, the Vilsmeier-Haack reaction conditions are: n, N-dimethylformamide is taken as a solvent, the mol ratio of the compound shown in the formula I' to phosphorus oxychloride is 1:10-20, and the reaction is carried out for 12-24 hours at the temperature of 80-100 ℃; the conditions of the Knoevenagel condensation reaction are as follows: chloroform, dichloromethane or 1, 2-dichloromethane is used as a solvent, a catalyst is pyridine, piperidine or triethylamine, the molar quantity of the catalyst is 0.1-10% of the molar quantity of a compound C, the molar ratio of EG to the compound C is 1:3-8, and the reaction is carried out for 0.1-24 hours at the temperature of 25-100 ℃.
The invention also provides an active layer comprising small organic molecules as described above and a p-type polymer donor material, wherein the small organic molecules act as acceptors; the active layer has stretchability.
The invention also provides an organic optoelectronic device, wherein the active layer adopts the active layer, and the organic optoelectronic device has stretchability.
Further, it is a thin film semiconductor device, a light emitting device, a photodetector, an organic photovoltaic device, a field effect transistor, a sensor, or a capacitor.
The invention also provides an organic optoelectronic device comprising the silane-substituted aromatic fused ring compound.
In general, through the above technical solutions conceived by the present invention, the following beneficial effects can be obtained:
(1) The invention discloses a silane-substituted aromatic fused ring compound and a high-efficiency intrinsic flexible stretchable photovoltaic cell. By introducing a silane group chain into a side chain structure of the small organic molecule, the small organic molecule acceptor material with excellent solubility and silane group substituted aromatic condensed rings is obtained. The material is tested by ultraviolet-visible absorption and the like, and has strong absorption to sunlight in a visible light region and a near infrared region, so that the material can be matched with the energy level of most of the existing wide-medium band gap p-type polymer donor materials, and has strong universality. As an n-type narrow band gap electron acceptor material, the material can be applied to an organic solar cell together with most of wide-medium band gap p-type polymer materials, and high energy conversion efficiency is obtained; meanwhile, the steel plate shows good mechanical properties in the external stress stretching process, is expected to become next-generation high-efficiency wearable power generation equipment.
(2) The silane-substituted aromatic fused ring compound can change the appearance of an active layer, so that when the organic micromolecule based on the silane-substituted aromatic fused ring containing organic fused ring is used as a non-fullerene organic electronic acceptor material, the silane-substituted aromatic fused ring containing organic fused ring is applied to an organic solar cell to obtain high energy conversion efficiency; meanwhile, it shows good intrinsic flexibility and tensile mechanical properties during external stress stretching.
Drawings
FIG. 1 is a schematic diagram of the synthesis of M according to example 2 of the present invention 2 Ultraviolet-visible absorption spectrum of the obtained product in the film state;
FIG. 2 is a synthetic M according to example 2 of the present invention 2 The obtained product is blended with PM6 to be used as an active layer to prepare a J-V curve of the organic solar cell device;
FIG. 3 is a synthetic M according to example 2 of the present invention 2 The resulting product was blended with PM6 to make an optical image of an organic stretchable film.
Detailed Description
The present invention will be described in further detail with reference to the drawings and examples, in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention. In addition, the technical features of the embodiments of the present invention described below may be combined with each other as long as they do not collide with each other.
The n-type small molecular receptor material obtained by analysis is one of important factors limiting the mechanical properties of the n-type small molecular receptor material because the mechanical properties such as the mechanical properties, tensile properties and the like of the organic solar cell at present can not meet the basic requirements of practical portable and wearable power generation equipment. Therefore, the invention designs and synthesizes a series of novel silane-substituted aromatic condensed ring organic small molecule acceptors as non-fullerene organic electron acceptor materials, and the novel silane-substituted aromatic condensed ring organic small molecule acceptors are matched with p-type polymer donor materials and applied to organic solar cells to obtain high energy conversion efficiency; meanwhile, it shows good intrinsic flexibility and tensile mechanical properties during external stress stretching. The concrete explanation is as follows:
the starting materials and reagents used in the examples below were commercially available unless otherwise specified.
In the examples described below, efforts are made to ensure accuracy with respect to numbers (including amounts, temperature, time, etc.), but some experimental errors and deviations should be accounted for. In the examples described below, the reaction is carried out under the protection of an inert gas, with the pressure used being at or near atmospheric pressure, unless otherwise specified.
Example 1
Silyl substituted aromatic condensed ring M 1 (i.e., the specific compound of formula I).
M 1 The synthetic route of (2) is shown in figure 2, and the specific reaction steps and reaction conditions are as follows:
Figure BDA0003383435960000071
a (7.47 g,10 mmol) was dissolved in anhydrous N, N-dimethylformamide (400 mL) under nitrogen, and after adding potassium carbonate (22.1 g,160 mmol), potassium iodide (1.9 g,11.5 mmol) and B (32.5 g,80 mmol), the mixture was reacted at 110℃for 48 hours. The quenching reaction was added, extracted three times with dichloromethane and washed three times with distilled water. Further purification by silica gel column chromatography using dichloromethane and petroleum ether (V: v=3:1) as eluent gave pale red solid (8.37 g, 60% yield) as compound M 1 。
The structure validation numbers are as follows: 1 H NMR(400MHz,CDCl 3 )δ7.00(s,2H),4.61(t,J＝7.2Hz,4H),2.81(t,J＝7.6Hz,4H),1.89-1.83(m,8H),1.49-1.07(m,84H),0.89-0.84(m,18H),0.41-0.34(m,8H),0.33-0.27(m,4H),-0.18(s,6H)。
example 2
Silyl substituted aromatic condensed ring M 2 (i.e., the specific compound of formula I').
M 2 The synthetic route of (2) is as follows:
Figure BDA0003383435960000081
the specific reaction steps and reaction conditions are as follows:
under the protection of nitrogen, M 1 (8.37 g,6 mmol) was dissolved in dry 1, 2-dichloroethane (40 mL) and reacted at 90℃for 12 hours with the addition of dry N, N-dimethylformamide (46 mL,600 mmol) and phosphorus oxychloride (11.2 mL,120 mmol). Adding the mixture into the quenching reaction,extraction was performed three times with dichloromethane and washing was performed three times with distilled water. Further purification by silica gel column chromatography using dichloromethane and petroleum ether (V: v=1:1) as eluent gave an orange solid (7.4 g, 85% yield) as compound C.
C (581 mg,0.4 mmol) and D (356 mg,3.2 mmol) were dissolved in anhydrous chloroform (45 mL) under nitrogen, and anhydrous pyridine (0.5 mL) was added to react at 75℃for 12 hours. Subsequently, the mixture was poured into methanol, the solid was taken after filtration, and further purified by a silica gel column chromatography using methylene chloride and petroleum ether (V: v=1:2) as eluent to give a blue-black solid (525 mg, yield 70%) as compound M 2 。
The structure validation numbers are as follows: 1 H NMR(400MHz,CDCl 3 )δ8.83(s,2H),8.47(dd,J＝9.6,6.6Hz,2H),7.62(t,J＝7.5Hz,2H),4.77-4.67(m,4H),3.08-2.98(m,4H),2.05-1.95(m,4H),1.82-1.73(m,4H),1.43-1.01(m,84H),0.89-0.85(m,6H),0.85-0.79(m,12H),0.40-0.27(m,12H),-0.20(s,6H)。
example 3
The uv-vis absorption of the molecules was determined using a uv-vis spectrometer.
For compound M synthesized in example 2 2 Film absorption testing was performed and the uv-vis absorption spectrum is shown in figure 1. It can be known that the material has stronger absorption to sunlight in the visible light region and the near infrared region, can be matched with the energy level of most of the existing wide-medium band gap p-type polymer donor materials, and has strong universality.
Example 4
Preparation and photovoltaic performance of organic solar cell devices.
Before the organic solar cell is manufactured, the patterned ITO glass substrate is sequentially cleaned for 20 minutes in an ultrasonic oscillator by using cleaning agents, deionized water, acetone and ethanol. After ultrasonic oscillation cleaning, the ITO glass substrate is subjected to surface treatment in an ultraviolet plasma cleaner for 60 seconds, and the ITO glass substrate is used as a cathode of an organic solar cell device. A PEDOT/PSS film was spin-coated on ITO glass.
The polymer donor material PM6 (the structural formula is shown below) and a small molecule acceptorMaterial M 2 Dissolving in chloroform at a ratio of 1:1.2, adding 0.5% chloronaphthalene as additive, and spin-coating on PEDOT: PSS film to form active layer film. Followed by spin coating of a layer F on the active layer 3 And finally, evaporating silver on the active layer to serve as an anode of the organic solar device. The final structure is ITO/PEDOT, PSS/PM6, M 2 /F 3 N/Ag photovoltaic devices.
Figure BDA0003383435960000101
All of the above device fabrication processes were performed in a glove box filled with nitrogen.
The energy conversion efficiency of the organic solar cell was measured by a J-V curve method under standard sunlight using an AM 1.5G solar simulator, the J-V curve of which is shown in fig. 2, and the photovoltaic performance of the device is shown in table 1.
Table 1:
Figure BDA0003383435960000102
from the results in table 1, it can be seen that the silane-substituted aromatic condensed ring organic small molecule acceptor material and the polymer donor material PM6 can still maintain a comparable energy conversion efficiency (> 15%).
In the above embodiments, the donor in the preparation of the active layer is not limited to the polymer donor material PM6, but can be replaced by other energy level matching, complementary absorbing donors, which also have good photovoltaic device performance in organic solar cells.
Example 5
Preparation and testing of organic stretchable films.
Polymer donor material PM6 and small molecule acceptor material M 2 Dissolving in chloroform at a ratio of 1:1.2, spin-coating on glass to form an organic stretchable film. It is then placed in water to separate the glass from the organic stretchable film. Finally, the organic stretchable film is placed in a stretching dieTensile testing was performed and an optical image was obtained (see fig. 3). A in fig. 3 is an optical image of an organic stretchable film that has not been subjected to a stretching test, and b in fig. 3 is an optical image of the organic stretchable film immediately after occurrence of a crack. As can be obtained from fig. 3, the film has very high stretchability, the stretchability is 30%, and the film is expected to be applied to wearable electronic equipment and has great application prospects.
In summary, the silane-substituted aromatic condensed ring compound can reduce the stacking between the silane-substituted aromatic condensed ring compound and change the appearance of an active layer, so that the silane-substituted aromatic condensed ring compound is applied to an organic solar cell to obtain high energy conversion efficiency when the organic small molecule based on the silane-substituted aromatic condensed ring compound is used as a non-fullerene organic electronic acceptor material; meanwhile, it shows good intrinsic flexibility and tensile mechanical properties during external stress stretching.
Therefore, the invention introduces the silane group chain into the non-fullerene acceptor, and introduces the silane group linkage, thereby changing the morphology of the acceptor, the donor and the two, so that the aggregation, the arrangement, the preparation and the like of the acceptor, the donor and the donor are obviously changed, the high efficiency can be maintained, the mechanical stretchability of the acceptor can be improved, and the acceptor, the donor and the donor can be effectively used for next-generation high-efficiency wearable power generation equipment.
It will be readily appreciated by those skilled in the art that the foregoing description is merely a preferred embodiment of the invention and is not intended to limit the invention, but any modifications, equivalents, improvements or alternatives falling within the spirit and principles of the invention are intended to be included within the scope of the invention.

Claims (7)

1. An organic small molecule based on a silyl substituted aromatic condensed ring structure is characterized in that the structure of the organic small molecule is shown as a formula I';
Figure QLYQS_1
i'
Wherein R is 1 , R 2 Respectively alkyl groups,Any one of alkoxy and substituted aryl, wherein the alkyl is one of straight-chain or branched-chain alkyl with 1-30 carbon atoms; the alkoxy is one of straight-chain or branched-chain alkoxy with 1-30 carbon atoms; the substituted aryl is one of alkyl with 6-20 carbon atoms and/or phenyl substituted by alkoxy with 1-30 carbon atoms;
R 3 ,R 4 the alkyl is one of straight-chain or branched-chain alkyl with 1-30 carbon atoms; the alkoxy is one of straight-chain or branched-chain alkoxy with 1-30 carbon atoms; the conjugated aryl is phenyl; the substituted aryl is one of alkyl with 1-30 carbon atoms and/or phenyl substituted by alkoxy with 1-30 carbon atoms;
R 5 is a linear alkylene group having 5 carbon atoms;
ar is a group of formula II:
Figure QLYQS_2
i
In the formula II, EG represents an electron withdrawing group and is any one of the following structures:
Figure QLYQS_3
wherein, represents the connection position, each R in the above EG structure 6 Each independently selected from one of hydrogen atom, alkyl, cycloalkyl, alkoxy, alkylthio, ester group and halogen substituent, wherein the alkyl, the alkoxy and the alkyl in the alkylthio are all one of straight-chain or branched-chain alkyl with 1-30 carbon atoms, and the cycloalkyl is one of cycloalkyl with 3-30 carbon atoms.
2. The small organic molecule of claim 1, wherein the small organic molecule has the following structure:
Figure QLYQS_4
。
3. an active layer comprising the small organic molecule of claim 1 or 2 and a p-type polymeric donor material, wherein the small organic molecule acts as a receptor; the active layer has stretchability.
4. An organic optoelectronic device, wherein the active layer of the organic optoelectronic device is the active layer of claim 3, and the organic optoelectronic device has stretchability.
5. An organic optoelectronic device according to claim 4, characterized in that it is a thin film semiconductor device, a photodetector, an organic photovoltaic device or a field effect transistor.
6. A method of synthesizing the small organic molecule according to claim 1 or 2, comprising:
s1, mixing a compound shown in the following formula I with phosphorus oxychlorideN,N-Dimethylformamide, through Vilsmeier-Haack reaction, compound C is obtained;
Figure QLYQS_5
i
S2, carrying out Knoevenagel condensation reaction on the compound C and the EG-containing compound to obtain the small organic molecule shown in the formula I';
wherein, the compound C has the following structure:
Figure QLYQS_6
；
the EG-containing compound is any one of the following structures:
Figure QLYQS_7
。
7. the method of claim 6, wherein the Vilsmeier-Haack reaction conditions are: to be used forN,N-Dimethylformamide is used as a solvent, the mol ratio of the compound shown in the formula I to phosphorus oxychloride is 1:10-20, and the reaction is carried out for 12-24 hours at the temperature of 80-100 ℃; the conditions of the Knoevenagel condensation reaction are as follows: chloroform, dichloromethane or 1, 2-dichloromethane is used as a solvent, a catalyst is pyridine, piperidine or triethylamine, the molar amount of the catalyst is 0.1-10% of the molar amount of the compound C, the molar ratio of the EG-containing compound to the compound C is 1:3-8, and the reaction is carried out for 0.1-24 hours at the temperature of 25-100 ℃.
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