Aza-p-benzoquinone as the core of a conjugated non-fullerene acceptor material and a preparation method and application thereof

Abstract

The application discloses a conjugated non-fullerene acceptor material with azaparacyclophanquinone as a core, and a structural general formula is shown as formula I: wherein R1 and R2 are C m H 2m+1 , m is greater than or equal to 1 and is an integer; and X is any one of H, F, Cl, Br and CN. The acceptor material has excellent performance, three-dimensional charge transport characteristics and good intermolecular stacking effect, and high electron mobility. When the material is applied to a binary organic photodetector, the material exhibits excellent near-infrared light detection performance, including high specific detectivity, high responsivity, fast response speed and low dark current density.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic materials technology, and more specifically to a conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core, its preparation method, and its application. Background Technology

[0002] With the ever-increasing demand for applications in environmental sensing, biomedical imaging, security monitoring, and optical communication, photodetectors capable of detecting the near-infrared spectral region are receiving unprecedented attention. While traditional inorganic detectors have applications in the near-infrared region, they suffer from limitations such as high cost, complex fabrication, brittleness, difficulty in large-area fabrication, and challenges in integration with flexible electronics. Therefore, developing novel, high-performance, low-cost, solution-processable, and flexible near-infrared photodetectors is of great significance.

[0003] Organic photodetectors have become a highly promising alternative due to their advantages such as wide availability of materials, low cost, high light absorption coefficient, light weight, good flexibility, and simple manufacturing process. In recent years, organic photodetectors have made significant progress in key performance parameters, especially detectivity, responsivity, and response speed, and their performance has approached or even surpassed that of traditional inorganic detectors in some aspects. The core challenge in the current research of high-performance near-infrared organic photodetectors lies in how to design and synthesize active layer materials that can efficiently absorb near-infrared photons, ensure efficient dissociation of photoexcitons, and enable the generated charge carriers to be transported quickly and with low loss and effectively collected by electrodes, while maintaining extremely low dark current noise. Therefore, the design and development of high-performance acceptor materials are crucial.

[0004] Ideal near-infrared organic photodetector materials require broad and strong absorption in the near-infrared region, appropriate HOMO and LUMO energy levels, high electron mobility, good stability, solubility, and film-forming properties, as well as good compatibility with donor materials. In recent years, the rapid development of non-fullerene small molecule acceptors has greatly promoted the research of high-performance organic photodetectors, especially in extending the near-infrared response. Compared with traditional fullerene derivatives, non-fullerene small molecule acceptors have significant advantages such as ease of synthesis and purification, lower cost, strong solubility, and easily tunable absorption spectra (especially the ability to design narrow optical band gaps to cover the near-infrared region), and can achieve good matching with a wide range of donor materials.

[0005] Therefore, how to provide a non-fullerene small molecule acceptor material with high specific detectivity, high responsivity, fast response speed and low dark current density is a problem that urgently needs to be solved by those skilled in the art. Summary of the Invention

[0006] In view of this, the present invention provides a conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as the core, its preparation method and application. The acceptor material of the present invention has excellent performance, with three-dimensional charge transport characteristics and good intermolecular stacking, and high electron mobility. When applied to binary organic photodetectors, the material exhibits excellent near-infrared light detection performance, including high specific detectivity, high responsivity, fast response speed and low dark current density.

[0007] To achieve the above objectives, the present invention adopts the following technical solution:

[0008] A conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core, the general structural formula of which is shown in Formula I:

[0009]

[0010] Where R1 and R2 are C m H 2m+1 m ≥ 1 and is an integer;

[0011] X is any one of H, F, Cl, Br, and CN.

[0012] This invention proposes a strategy for conjugated non-fullerene organic small molecule materials based on the aza-p-methylenebenzoquinone structure. Compared to traditional aromatic conjugated systems, a quinone-type conjugated system with unique electronic structure characteristics is chosen as the central unit. The imine nitrogen atom introduced into the framework not only solves the stability problem caused by the easy conversion of p-methylenebenzoquinone into highly reactive biradical species, but also utilizes the weak intramolecular interactions brought by the nitrogen atom to lock the configuration of the quinone monomer. The quinone structural unit has a rigid planar framework, reducing intramolecular torsion, promoting π-π stacking, and improving crystallinity. The quinone resonance structure can form an extended delocalized π-electron system, significantly broadening the light absorption range. The rigid quinone framework reduces molecular vibrational energy loss, lowers recombination energy, and improves electron mobility. The acceptor molecule of this invention differs from Y6-type fused-ring small molecules, requiring fewer synthesis steps and lowering costs while maintaining high energy conversion efficiency and high stability.

[0013] Preferably, R1 and R2 are at least one selected from 2-ethylhexyl, 2-butyloctyl, and 2-hexyldecyl.

[0014] Preferably, X is F or Cl.

[0015] Preferably, the structural formulas are as follows:

[0016]

[0017]

[0018] A method for preparing a conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core, as described above, includes the following steps:

[0019] (1) Compound A was obtained by reacting cyclopentylthiophene with bromoalkyl, potassium iodide and potassium hydroxide;

[0020] (2) Compound A was reacted with n-butyllithium and DMF to introduce an aldehyde group to obtain compound B;

[0021] (3) Compound B was sequentially condensed with 1,4-diacetylpiperazine-2,5-dione and bromoalkyl to obtain compound C;

[0022] (4) Compound C was reacted with phosphorus oxychloride and DMF via a Vilsmeier-Haack reaction to introduce a dialdehyde group to obtain compound D;

[0023] (5) The compound D is obtained by Knoevenagel polycondensation reaction with end unit, hexanoic anhydride and boron trifluoride diethyl ether, which is a conjugated nonfullerene acceptor material with aza-p-methylenebenzoquinone as the core.

[0024] Wherein, the structural formula of compound A is

[0025] The structural formula of compound B is as follows:

[0026] The structural formula of compound C is as follows:

[0027] The structural formula of compound D is as follows:

[0028] Preferably, the molar ratio of the cyclopentylthiophene, the bromoalkyl group, the potassium iodide, and the potassium hydroxide in step (1) is 1:1-3:0.5-3:1-5, and more preferably 1:2.68:1.04:3.28; the bromoalkyl group corresponds to R1;

[0029] The reaction was carried out under the condition of stirring at room temperature for 12 hours.

[0030] Preferably, the molar ratio of compound A, n-butyllithium and DMF in step (2) is 1:0.8-1.2:1-3, and more preferably 1:0.95:1.5;

[0031] The reaction conditions were as follows: n-butyllithium was added dropwise to compound A at -78°C, and DMF was added after stirring at -78°C for 1.5 h. The mixture was then brought to room temperature and stirred for 12 h.

[0032] Preferably, in step (3), the molar ratio of compound B, the 1,4-diacetylpiperazine-2,5-dione, and the bromoalkyl group is 2-5:1:2-5, preferably 2.8:1:3; the bromoalkyl group corresponds to R2;

[0033] The reaction conditions for the 1,4-diacetylpiperazine-2,5-dione and bromoalkyl groups were all: stirring at room temperature for 24 h.

[0034] Preferably, the molar ratio of compound C, phosphorus oxychloride and DMF in step (4) is 1:2-50:2-200, and more preferably 1:30:120;

[0035] The conditions for the Vilsmeier-Haack reaction were: stirring at 50°C for 12 hours.

[0036] Preferably, the molar ratio of compound D, the terminal unit, the hexanoic anhydride and the boron trifluoride diethyl ether in step (5) is 1:2-6:3-10:3-20, and more preferably 1:5:7:14;

[0037] The terminal unit is 3-(dicyanomethylene)indoketone;

[0038] The conditions for the Knoevenagel polycondensation reaction were: stirring at room temperature for 15 minutes.

[0039] The above-described application of a conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core in the fabrication of organic photodetector devices, wherein the conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core serves as the acceptor material in the active layer of the organic photodetector device.

[0040] Preferably, the active layer further includes a donor material, wherein the donor material is PTB7-Th; the mass ratio of PTB7-Th to the conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core is 1:1.5.

[0041] The aforementioned organic electroluminescent device includes: an organic photodetector device comprising, in sequence, an ITO substrate, a ZnO layer, an active layer, a molybdenum trioxide layer, and an electrode, wherein the active layer comprises the aforementioned active layer.

[0042] As can be seen from the above technical solution, compared with the prior art, the beneficial effects of the present invention are as follows:

[0043] (1) This invention abandons the traditional ADA structure with Y-series analogs as the core and innovatively uses the aza-p-methylenebenzoquinone structure as the core to design a conjugated non-fullerene organic small molecule acceptor material with an AD-A'-DA type skeleton. The design selects a quinone conjugated system with unique electronic structure characteristics as the central unit. This core structure has significant advantages such as enhancing near-infrared absorption and charge generation, improving charge transport efficiency and response speed, reducing energy loss, and having relatively simple material synthesis route and reaction conditions, and has good potential for practical application.

[0044] (2) By introducing IC as a terminal group, this invention effectively broadens the absorption spectrum of the molecule and improves the absorption coefficient. At the same time, it reduces the HOMO energy level of the small molecule material. The reduction of the HOMO energy level helps to form a more optimized energy level match with the donor material, promotes exciton dissociation, and effectively suppresses the generation of dark current. By introducing different alkyl chains into the side chain, the spatial interaction between them and the main chain can be used to finely control the molecular stacking mode, energy level position and solubility, which is conducive to forming an efficient charge transport network and facilitates solution processing to prepare high-performance devices. When applied to near-infrared organic photodetectors, it can achieve efficient near-infrared photogenerated charge generation, separation and transport, and finally exhibit excellent detection performance at the device level, including high specific detectivity, high responsivity, fast response speed and low dark current density. Attached Figure Description

[0045] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. The drawings in this description are merely embodiments of the present invention.

[0046] Figure 1 Compound (II) prepared in this invention 1 H NMR spectrum;

[0047] Figure 2 Compound (III) prepared in this invention 1 H NMR spectrum;

[0048] Figure 3 Compound (IV) prepared in this invention 1 H NMR spectrum;

[0049] Figure 4 The compound (V) prepared in this invention 1 H NMR spectrum;

[0050] Figure 5 The compound PZ-CPDT-4F prepared in this invention 1 H NMR spectrum;

[0051] Figure 6 The compound PZ-CPDT-4Cl prepared in this invention 1 H NMR spectrum;

[0052] Figure 7 UV spectra of compounds PZ-CPDT-4F and PZ-CPDT-4Cl prepared in this invention;

[0053] Figure 8 EQE curves of compounds PZ-CPDT-4F and PZ-CPDT-4Cl prepared for this invention;

[0054] Figure 9 CV curves of compounds PZ-CPDT-4F and PZ-CPDT-4Cl prepared for this invention;

[0055] Figure 10 Dark current curves of compounds PZ-CPDT-4F and PZ-CPDT-4Cl prepared for this invention;

[0056] Figure 11 Specific detectivity curves of compounds PZ-CPDT-4F and PZ-CPDT-4Cl prepared for this invention;

[0057] Figure 12 The response curves of compounds PZ-CPDT-4F and PZ-CPDT-4Cl prepared for this invention. Detailed Implementation

[0058] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0059] Unless otherwise specified, the "water" used in the following examples is deionized water.

[0060] In the following tests of this invention, proton nuclear magnetic resonance (NMR) spectra were performed on an AVANCE NEO 500MHz superconducting NMR spectrometer from Bruker GmbH, Germany. The solvent used was deuterated chloroform (CDCl3), and the instrument was calibrated with tetramethylsilane (TMS).

[0061] Example 1

[0062] The synthetic route for preparing compound PZ-CPDT-4F is as follows:

[0063]

[0064] The specific preparation method includes the following steps:

[0065] (1) Synthesis of compound (II):

[0066] At 0 °C, 1-bromo-2-butyloctane (11.24 g, 45.10 mmol), potassium iodide (0.39 g, 2.36 mmol), and potassium hydroxide (3.10 g, 55.20 mmol) were added sequentially to a dimethyl sulfoxide (40 mL) solution of cyclopentylthiophene (3.00 g, 16.83 mmol). The mixture was stirred at 1200 rpm for 12 h at room temperature. After the reaction was confirmed to be complete by thin-layer chromatography, the reaction solution was poured into ice water (100 mL), and the organic phase was extracted with 50 mL of dichloromethane (3 times). The solution was dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The solution was then purified by rapid column chromatography (eluent: 100% petroleum ether) to obtain a colorless oily liquid, which was compound (II) (7.02 g, yield of 81.01% in this step). 1 The H NMR spectrum is shown in [reference]. Figure 1 ;

[0067] (2) Synthesis of compound (III):

[0068] Anhydrous tetrahydrofuran (40 mL) was added to compound (II) (4.00 g, 7.77 mmol) under a nitrogen atmosphere at -78 °C. 2.5 M n-butyllithium (0.47 g, 7.38 mmol) was added dropwise at -78 °C. After stirring at -78 °C for 1.5 h, N,N-dimethylformamide (0.85 g, 11.65 mmol) was added. The mixture was then gradually brought to room temperature and stirred at 1200 rpm for 12 h. After the reaction was confirmed to be complete by thin-layer chromatography, deionized water (100 mL) was added to quench the reaction. The organic phase was extracted with 50 mL of dichloromethane (3 times). The mixture was dried over anhydrous Na₂SO₄, and the solvent was removed under reduced pressure. The crude product was purified by rapid column chromatography (petroleum ether:dichloromethane = 2:1) to give a yellow oily liquid compound (III) (3.80 g, yield of 90.10% in this step). 1 The H NMR spectrum is shown in [reference]. Figure 2 ;

[0069] (3) Synthesis of compound (IV):

[0070] Under a nitrogen atmosphere, compound (III) (3.84 g, 7.06 mmol), potassium carbonate (2.09 g, 15.14 mmol), and triethylamine (0.77 g, 7.57 mmol) were added to a DMF (20 mL) solution of compound 1,4-diacetylpiperazine-2,5-dione (0.50 g, 2.52 mmol). The mixture was stirred at 1200 rpm for 24 h at room temperature. After the starting material disappeared as detected by thin-layer chromatography, 1-bromo-2-hexyldecane (2... 0.31 g (7.57 mmol), stirred at 1200 rpm for 24 h at room temperature. After the reaction was confirmed to be complete by thin-layer chromatography, deionized water (100 mL) was added to quench the reaction. The organic phase was extracted with 50 mL of dichloromethane (3 times), washed 3 times with 50 mL of saturated brine, dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by rapid column chromatography (100% petroleum ether) to obtain a purple oily liquid compound (IV) (1.50 g, yield of 36.86% in this step). 1 The H NMR spectrum is shown in [reference]. Figure 3 ;

[0071] (4) Synthesis of compound (V):

[0072] Under a nitrogen atmosphere at 0°C, a mixed solution of phosphorus oxychloride (0.71 g, 4.65 mmol) and DMF (2.72 g, 37.20 mmol) was added to a solution of compound (IV) (0.25 g, 0.16 mmol) in 1,2-dichloroethane (10 mL). The mixture was then heated to 50°C and stirred at 1200 rpm for 12 h. After the reaction was confirmed to be complete by thin-layer chromatography, the reaction solution was poured into a saturated sodium carbonate (100 mL) solution and stirred for 2 h to allow the product to be fully hydrolyzed. The organic phase was extracted three times with 50 mL of dichloromethane, washed three times with 50 mL of saturated brine, dried over anhydrous Na₂SO₄, and the solvent was removed under reduced pressure. The crude product was purified by rapid column chromatography (petroleum ether:dichloromethane = 2:1) to give a blue oily liquid compound (V) (0.2 g, yield of 77.31% in this step). 1 The H NMR spectrum is shown in [reference]. Figure 4 ;

[0073] (5) Synthesis of compound PZ-CPDT-4F:

[0074] To a toluene (15 mL) solution of compound (V) (0.40 g, 0.240 mmol), terminal groups of 5,6-difluoro-3-(dicyanomethylene)indophenone (0.28 g, 1.20 mmol), boron trifluoride diethyl ether (0.48 g, 3.36 mmol), and hexanoic anhydride (0.36 g, 1.68 mmol) were added. The reaction mixture was stirred at 1200 rpm for 15 min at room temperature. After the reaction was confirmed to be complete by thin-layer chromatography, the reaction mixture was added dropwise to methanol (100 mL), and the solid was collected by filtration. The crude product was purified by rapid column chromatography (petroleum ether: dichloromethane at a ratio of 2:1) to obtain a blackish-purple solid PZ-CPDT-4F (260 mg, yield of 51.82% in this step). 1 The H NMR spectrum is shown in [reference]. Figure 5 .

[0075] Example 2

[0076] The synthetic route for preparing compound PZ-CPDT-4Cl is as follows:

[0077]

[0078] The specific preparation method includes the following steps:

[0079] Steps (1)-(4) are the same as in Example 1;

[0080] (5) Synthesis of compound PZ-CPDT-4Cl:

[0081] To a toluene (15 mL) solution of compound (V) (0.40 g, 0.240 mmol), terminal groups of 5,6-dichloro-3-(dicyanomethylene)indophenone (0.32 g, 1.20 mmol), boron trifluoride diethyl ether (0.48 g, 3.36 mmol), and hexanoic anhydride (0.36 g, 1.68 mmol) were added. The reaction mixture was stirred at room temperature for 15 min. After the reaction was confirmed to be complete by thin-layer chromatography, the reaction mixture was added dropwise to methanol (100 mL), and the solid was collected by filtration. The crude product was purified by rapid column chromatography (petroleum ether: dichloromethane at a ratio of 2:1) to obtain a dark purple solid PZ-CPDT-4Cl (270 mg, yield of 52.18% in this step). 1 See the HNMR spectrum. Figure 6 .

[0082] Device Example 1

[0083] To further illustrate the application effect of the conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core prepared in this invention in organic photodetector devices, the following test experiments were conducted, as follows:

[0084] (1) After ultrasonic cleaning, ITO glass (indium tin oxide conductive glass) was treated with ozone using a plasma cleaner. 440 mg of zinc acetate dihydrate was dissolved in 4 mL of ethylene glycol methyl ether, and 120 μL of ethanolamine was added to prepare a zinc oxide precursor solution. The zinc oxide precursor solution was then stirred overnight at 55 °C. ZnO thin film was prepared by spin-coating the ZnO precursor solution onto ITO glass at 4000 rpm and annealing it in air at 200 °C for 60 minutes to obtain a substrate with a surface film thickness of about 25 nm.

[0085] (2) Using the small molecule compounds PZ-CPDT-4F and PZ-CPDT-4Cl prepared in Examples 1 and 2 as acceptor materials, respectively, and mixing them with the donor PTB7-Th to form a binary organic photodetector device (the preferred mass ratio of donor and acceptor materials is 1:1.5), chloroform solvent was added to prepare a blend solution (the total concentration of donor and acceptor is 15 mg / mL). The blend solution was then coated onto the substrate from step (1) using a spin coating speed of 3000 rpm, and an active layer with a thickness of approximately 160 nm was coated on the substrate surface. The structural formula of PTB7-Th is as follows:

[0086] (3) The substrate obtained in step (2) is thermally annealed (110°C, 10 min). Next, an 8 nm MoO3 dense film is vacuum deposited. Finally, a 100 nm thick silver layer is deposited on top of the electron transport layer by vapor deposition.

[0087] The specific performance of the photodetector is shown in Table 1 and... Figure 10-12 As shown (the equipment used in the laboratory of this invention is a 7SCSpec solar cell testing system, calibrated using a silicon standard photodetector);

[0088] Table 1 External quantum efficiency of photovoltaic devices

[0089]

[0090] As can be seen from the data in Table 1, the binary organic photodetector devices prepared by using the compounds PZ-CPDT-4F and PZ-CPDT-4Cl prepared in this invention as acceptors have good performance. The proposed small molecules have unique and well-defined molecular structures in organic photodetectors, and the batch-to-batch differences in materials and devices are very small. Therefore, they have unique advantages in the commercialization of organic photodetectors.

[0091] Figure 7The UV-Vis spectra of the solution and film were recorded using a Hitachi U-4100 UV-Vis spectrophotometer. The solution absorption test sample was dissolved in chloroform at a concentration of 0.01 mg / mL and measured at room temperature. The optical absorption spectrum of the film was prepared by spin-coating a chloroform solution (15.0 mg / mL, 3000 rpm) onto a quartz plate. As can be seen from the figure, the maximum absorption peak of compound PZ-CPDT-4Cl in the solution absorption spectrum is red-shifted by about 20 nm compared to compound PZ-CPDT-4F. Compared to PZ-CPDT-4F, PZ-CPDT-4Cl in the film has a wider absorption range, which indicates that the sterically hindered small molecules have good intermolecular stacking, which helps to improve charge mobility.

[0092] Figure 8 The external quantum efficiency (EQE) test results are shown. The EQE spectrum was tested and analyzed using a certified 7SCSpec solar cell test system. This test corroborates the EQE spectrum of the PTB7-Th:PZ-CPDT-4Cl binary device compared to the integral of the solar spectrum (AM 1.5G) with that of the PTB7-Th:PZ-CPDT-4F-based binary device. SC Consistent with the values ​​obtained from the JV curve, with an error of less than 5%, this means that PZ-CPDT-4F and PZ-CPDT-4Cl have more efficient internal charge transfer and more absorbed photons to generate charge carriers;

[0093] Figure 9 For electrochemical testing results, a three-electrode system (glassy carbon electrode as working electrode, Ag / Ag) was used on a CHI660D electrochemical workstation. + The electrode was used as a reference electrode and a platinum wire counter electrode. Cyclic voltammetry (CV) was performed using a nitrogen-saturated solution of 0.1 mol / L tetrabutylammonium hexafluorophosphate in acetonitrile as the electrolyte, with a scan rate of 100 mV / s. Ferrocene-ferrocene salt (Fc / Fc+) was used as an internal standard. The absolute energy compared to vacuum was -4.7 eV. The HOMO and LUMO energy levels of the material were determined according to the equation. Figure 9 The HOMO level of compound PZ-CPDT-4F is calculated to be -5.31 eV, and its LUMO level is -3.92 eV. The HOMO level of compound PZ-CPDT-4Cl is -5.37 eV, and its LUMO level is -3.96 eV. This is beneficial for exciton dissociation and improves the photoelectric conversion efficiency of photovoltaic devices.

[0094] The various embodiments in this specification are described in a progressive manner, with each embodiment focusing on its differences from other embodiments. Similar or identical parts between embodiments can be referred to interchangeably. For the apparatus disclosed in the embodiments, since they correspond to the methods disclosed in the embodiments, the description is relatively simple; relevant parts can be referred to the method section.

[0095] The above description of the disclosed embodiments enables those skilled in the art to make or use the invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the invention. Therefore, the invention is not to be limited to the embodiments shown herein, but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core, characterized in that, The general structural formula of the conjugated non-fullerene acceptor material is shown in Formula I: ； Formula I Where R1 and R2 are C m H 2m+1 m ≥ 1 and is an integer; X is any one of H, F, Cl, Br, and CN.

2. The conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core according to claim 1, characterized in that, R1 and R2 are at least one of 2-ethylhexyl, 2-butyloctyl, and 2-hexyldecyl.

3. The conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core according to claim 1, characterized in that, X is either F or Cl.

4. The application of the conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core as described in any one of claims 1-3 in the fabrication of organic photodetector devices, characterized in that, The conjugated non-fullerene acceptor material with aza-p-methylenebenzoquinone as its core is used as the acceptor material in the active layer of the organic photodetector device.

Images