Self-assembled high-entropy charge transfer luminescent material as well as preparation method and application thereof

By designing self-assembled high-entropy charge-transfer luminescent materials, the problem of insufficient functional integration in traditional organic semiconductor materials has been solved, and the performance of optoelectronic devices has been improved, especially in terms of luminescence and charge transport optimization.

CN121045261APending Publication Date: 2025-12-02XIAMEN UNIV
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Patent Information

Application Number
CN202511159252.3
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-08-19
Publication Date
2025-12-02

AI Technical Summary

Technical Problem

Traditional organic semiconductor materials have shortcomings in terms of functional integration and tunability, which limits the performance improvement of optoelectronic devices.

Method used

By employing self-assembled high-entropy charge-transfer luminescent materials, a DA configuration is formed through the combination of electron donor unit D, electron acceptor unit A, and end group unit E. The electron donor/acceptor intensity and end group type are adjusted by connecting them through alkyl chains or alkoxy chains, thereby achieving multifunctional luminescence and charge transport.

Benefits of technology

It improves the luminous efficiency, stability, and carrier transport capability of optoelectronic devices, and is suitable for functional layer and interface modification of various optoelectronic devices, thereby enhancing the overall performance of the devices.

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Abstract

The invention discloses a self-assembled high-entropy charge transfer luminescent material and a preparation method thereof, and belongs to the technical field of organic photoelectric materials. The main structure of the material is characterized in that the material simultaneously comprises a donor-acceptor type charge transfer luminescence unit formed by an electron donor unit D and an electron acceptor unit A, and an end group as a self-assembly anchoring group, so that the integration of multiple functions such as efficient luminescence, energy transfer and interface / layer self-assembly can be realized; by adjusting the electron donor / acceptor intensity and the terminal group type, the properties such as optical band gap, exciton generation and utilization efficiency, self-assembly behavior, carrier transport and the like are regulated and controlled, multifunctional application in photoelectric devices can be realized, and the comprehensive performance of the photoelectric devices can be synergistically improved.
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Description

Technical Field

[0001] This invention belongs to the technical field of organic optoelectronic materials, specifically relating to a self-assembled high-entropy charge-transfer luminescent material, its preparation method, and its application. Background Technology

[0002] Organic semiconductor materials, due to their advantages such as strong structural designability, tunable photoelectric properties, and flexible fabrication processes, have shown great application potential in the field of optoelectronic devices. They can be applied to various devices, including organic light-emitting diodes (OLEDs), organic photovoltaic devices (OPVs), organic photodetectors (OPDs), quantum dot light-emitting diodes (QLEDs), and perovskite optoelectronic devices, enabling the integration of multiple optoelectronic functions. Taking OLEDs as an example, as a typical multilayer thin-film device, they typically include functional layers such as cathode, anode, hole injection / transport layer (HIL / HTL), electron injection / transport layer (EIL / ETL), and emissive layer (EML). The performance of the organic semiconductor materials applied to each functional layer directly affects the device's luminous efficiency, stability, and energy consumption.

[0003] Traditional organic semiconductor materials suffer from technical bottlenecks such as insufficient functional integration and poor tunability, which restricts device development in areas such as exciton management capabilities, carrier transport efficiency, and interface performance. From a molecular design perspective, functional modification and rational design of organic semiconductor materials will lay the foundation for synergistic improvement of overall device performance. Summary of the Invention

[0004] This invention provides a self-assembled high-entropy charge-transfer luminescent material, its preparation method, and its application, which can realize multiple functions such as exciton generation, carrier transport, and interface modification, thereby laying the foundation for the synergistic improvement of device performance.

[0005] To achieve the above objectives, the technical solution of the present invention is as follows:

[0006] A self-assembled high-entropy charge-transfer luminescent material includes an electron donor unit D, an electron acceptor unit A, and a terminal unit E. The electron donor unit D and the electron acceptor unit A form a DA configuration. The terminal unit E is connected to at least one end of the electron donor unit D and the electron acceptor unit A via an alkyl chain or an alkoxy chain. The electron donor unit D includes aromatic amines and their derivatives, aromatic amine heterocycles and their derivatives, and the electron acceptor unit A includes benzophenone and its derivatives, diphenyl sulfone and its derivatives, and triazine and its derivatives. The terminal unit E includes a phosphate group, a carboxyl group, and an amino group.

[0007] Optionally, the self-assembled high-entropy charge-transfer luminescent material has the structure shown in formula (1), formula (2), or formula (3):

[0008]

[0009] Where n is the number of carbon atoms in the alkyl chain or alkoxy chain, ranging from 1 to 10000; the number of carbon atoms is taken from positive integers, such as 1, 2, 3, ...;

[0010] In equation (3), the E on both sides may be the same or different.

[0011] Optionally, the structure of the electron donor unit D includes:

[0012]

[0013] Wherein, X is selected from oxygen atom, sulfur atom, selenium atom, C1-10 alkyl or aryl substituted tertiary amino group, 13-20 membered heterocyclic group, substituted or unsubstituted -B(C 6-20 Aryl)-、-B(C 5-25 One of the heteroaryl groups; Y and Y' are each independently selected from hydrogen atoms, halogens, and C. 6-20 Aryl, C 5-25 One of the heteroaryl groups. The dashed line indicates whether the lines are connected or disconnected.

[0014] Optionally, the structure of the electron acceptor unit A is preferably a substituted or unsubstituted diphenyl sulfone or benzophenone derivative, having the structural features of formula (6), (7), (8), or (9); or selected from 2,4,6-triphenyltriazine groups, having the structural features of formula (10):

[0015]

[0016] Wherein, Z is selected from oxygen atom, sulfur atom, selenium atom, C1-10 alkyl or aryl substituted tertiary amino group, 13-20 membered heterocyclic group, spirocyclic group, substituted or unsubstituted -B(C 6-20 Aryl)-、-B(C 5-25 One of the aromatic compounds (Aromatica).

[0017] Optionally, the electron donor unit D and the electron acceptor unit A are directly connected, conjugately bridged, non-conjugately bridged, or spatially twisted connected.

[0018] Optionally, the self-assembled high-entropy charge-transfer luminescent material includes, but is not limited to, the following structures:

[0019]

[0020]

[0021] Furthermore, the above structural formula is only for demonstrating the concept of the present invention. Based on this, common modifications should be included within the scope of protection of the present invention, such as introducing an E group unit on the basis of aryl or heteroaryl, or substituting or fusion modifications on the periphery of D and A units; or introducing phenyl or other conjugated groups between D and A units; or isomerizing combinations between D and A units, etc.

[0022] In this invention, "C" 6~60 "Aryl" can be understood as a monocyclic, bicyclic, or tricyclic hydrocarbon system with 6-60 carbon atoms, exhibiting monovalent aromaticity or partial aromaticity. Similarly, "C 6~20 Aryl"C" 5~20 The term "aryl" can be understood in a similar way, except for the difference in the number of carbon atoms.

[0023] “C 5~60 "Heteroaryl" can be understood as a monocyclic, bicyclic, or tricyclic hydrocarbon system containing 5-60 carbon atoms, and the system contains 1-5 heteroatoms independently selected from nitrogen, oxygen, and sulfur. 5-20 The term "heteroaryl" can be understood in a similar way, except for the difference in the number of carbon atoms.

[0024] A method for preparing the above-mentioned self-assembled high-entropy charge-transfer luminescent material includes the following steps:

[0025] Synthesize intermediates containing DA structures;

[0026] An end group E, connected by an alkyl chain or alkoxy chain, is formed at at least one end of the electron donor unit D or electron acceptor unit A of the intermediate through a substitution reaction or grafting reaction.

[0027] Optionally, the preparation method includes the following steps:

[0028] 1) 4-Bromobenzenesulfonyl chloride or 4-bromobenzoyl chloride is reacted with 3-phenylpropyl bromide to obtain a derivative based on diphenyl sulfone or benzophenone as an intermediate containing the A structure, wherein the benzene ring is connected to the bromine atom at the end of the carbon chain.

[0029] 2) React an intermediate containing structure A with a compound containing structure D to synthesize an intermediate containing structure DA;

[0030] 3) Replace the bromine atom at the end of the carbon chain of the intermediate containing the DA structure with the end unit E to obtain the self-assembled high-entropy charge-transfer luminescent material.

[0031] An optoelectronic device having the aforementioned self-assembled high-entropy charge-transfer luminescent material.

[0032] Optionally, the optoelectronic device includes an electroluminescent device, a photovoltaic device, and a photodetector.

[0033] Optionally, the optoelectronic device is a thin-film optoelectronic device, the structure of which includes an anode, a cathode, an organic functional layer located between the anode and the cathode, and a light-emitting (photosensitive) layer located between the anode and the cathode; a hole injection layer and a hole transport layer are located between the light-emitting (photosensitive) layer and the anode; an electron transport layer and an electron injection layer are located between the light-emitting (photosensitive) layer and the cathode; the light-emitting (photosensitive) layer may include one or more combinations of host, guest material, or donor and acceptor materials.

[0034] More preferably, when the thin-film optoelectronic device is a light-emitting layer, it is an organic electroluminescent device.

[0035] The thin-film optoelectronic device can be fabricated using methods such as vacuum evaporation, spin coating, and inkjet printing.

[0036] As one specific implementation, the self-assembled high-entropy charge-transfer luminescent material is located in the hole transport layer, which can achieve low interface resistance and high-efficiency exciton generation or dissociation performance.

[0037] In one specific implementation, the self-assembled high-entropy charge-transfer luminescent material is used in the luminescent layer.

[0038] The beneficial effects of this invention are as follows:

[0039] (1) The self-assembled high-entropy charge-transfer luminescent material of the present invention connects the charge-transfer luminescent unit with electron donor and electron acceptor to the terminal functional unit through alkyl chain / alkoxy chain. By adjusting the intensity of electron donor / electron acceptor and the type of end group, it can achieve multiple functions of luminescence with different band gaps and different charge injection / transmission, and can be applied to a variety of optoelectronic devices including organic thin film optoelectronic devices.

[0040] (2) Based on the light-emitting unit, the present invention introduces active and stable anchoring groups through reasonable molecular design, which is beneficial to the bonding with the surface of materials such as ITO, adjusts the work function of ITO, forms strong dipoles through chemical adsorption, enhances the stability of the device and the carrier transport capability, and thus improves the overall performance of optoelectronic devices.

[0041] (3) The structure of the self-assembled high-entropy charge-transfer luminescent material described in this invention is determinable, the synthesis process is simple, and it is suitable for industrial-scale mass production.

[0042] Other features and advantages of the invention will be set forth in the following description, and will be apparent in part from the description, or may be learned by practicing the invention. Attached Figure Description

[0043] Figure 1 This is a schematic diagram of the thin-film electroluminescent device in Example 4;

[0044] Figure 2 The device of Example 4 uses the electroluminescence spectrum of compounds 1-2 from Example 1 as the emitting layer. Detailed Implementation

[0045] To provide further explanation, the following specific embodiments are provided. It should be understood that these are only examples of some of the embodiments and do not cover all implementations of the present invention, nor do they limit the content and scope of protection of the present invention.

[0046] Unless otherwise specified, the starting reactants used in the examples can be obtained commercially available or through known synthetic methods.

[0047] Example 1: Synthesis of Compounds 1-2

[0048] The synthetic route for compound L1 is shown below:

[0049]

[0050] Under a nitrogen atmosphere, 4-bromobenzenesulfonyl chloride (8.17 g, 32 mmol), 3-phenylpropyl bromide (19.1 g, 96 mmol), and AlCl3 (4.78 g, 35.84 mmol) were mixed and stirred at room temperature for 12 hours. After the reaction was completed, the reaction mixture was extracted with dichloromethane and saturated brine. The organic phase was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give a white solid product L1 (12.7 g, yield: 95%).

[0051] MS (EI): m / z 417.91 [M+]; Combustion-based elemental analysis: C 15 H 14 Calculated values ​​of Br2O2S (%): C, 43.09; H, 3.37; Br, 38.22; O, 7.65; S, 7.67; Measured values: C, 42.99; H, 3.30; O, 7.64.

[0052] The synthetic route for compound L2 is shown below:

[0053]

[0054] Under a nitrogen atmosphere, L1 (5.0 g, 12 mmol), 9,9-dimethylacridine (2.51 g, 12 mmol), palladium acetate (135 mg, 0.6 mmol), potassium tert-butoxide (14.4 mmol, 1.62 g), tritert-butylphosphine tetrafluoroborate (279 mg, 0.96 mmol), and anhydrous toluene (30 mL) were added sequentially to a Schlenk reaction tube. After three gas purgings, the mixture was heated to 120 °C and refluxed for 24 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and saturated brine. The organic phase was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography to give a white solid product L2 (4.98 g, yield: 76%).

[0055] MS (EI): m / z 547.1 [M+]; Combustion-based elemental analysis: C 30 H 28 Calculated values ​​of BrNO2S (%): C, 65.93; H, 5.16; Br, 14.62; N, 2.56; O, 5.85; S, 5.87; Measured values: C, 65.99; H, 5.13; O, 5.74; N, 2.50.

[0056] The synthetic route for compound L3 is shown below:

[0057]

[0058] Under a nitrogen atmosphere, L2 (8 mmol, 4.37 g) and triethyl phosphite (200 mmol, 3.3 g) were added sequentially to a Schlenk reaction tube. After three gas changes, the mixture was heated to 165 °C and refluxed overnight. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and saturated brine. The organic phase was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography to give a white solid product L3 (4.35 g, yield: 90%).

[0059] MS (EI): m / z 603.22 [M+]; Combustion-based elemental analysis: C 34 H 38 NO5PS (%) Calculated values: C, 67.64; H, 6.34; N, 2.32; O, 13.25; P, 5.13; S, 5.31; Measured values: C, 67.59; H, 6.33; O, 13.04; N, 2.28.

[0060] The synthetic routes for compounds 1-2 are shown below:

[0061]

[0062] Under a nitrogen atmosphere, compound L3 (3.02 g, 5.0 mmol) was dissolved in anhydrous 1,4-dioxane (11 ml). Trimethylbromosilane (995 mg, 6.5 mmol) was added dropwise at room temperature, and the mixture was stirred for 24 hours. Subsequently, some of the solvent was removed by vacuum distillation. Methanol was slowly added to the remaining liquid, followed by dropwise addition of distilled water until the solution became turbid. The filtrate was filtered off, and the collected product was washed repeatedly with water and dried in a vacuum oven to obtain a gray solid product 1-2 (1.94 g, yield: 71%).

[0063] MS (EI): m / z 547.16 [M+]; Combustion-based elemental analysis: C 30 H 30 NO5PS (%) Calculated values: C, 65.80; H, 5.52; N, 2.56; O, 14.61; P, 5.66; S, 5.85; Measured values: C, 65.69; H, 5.53; O, 14.64; N, 2.58.

[0064] Example 2: Synthesis of compounds 1-20

[0065] The synthetic route for compound L4 is shown below:

[0066]

[0067] Under a nitrogen atmosphere, 4-bromobenzoylbenzene (2.61 g, 10.0 mmol), 9,9-dimethylacridine (2.09 g, 10 mmol), palladium acetate (113 mg, 0.5 mmol), potassium tert-butoxide (12 mmol, 1.35 g), tritert-butylphosphine tetrafluoroborate (189 mg, 0.65 mmol), and anhydrous toluene (20 mL) were added sequentially to a 250 mL Schlenk flask. After three gas purgings, the mixture was heated to 120 °C and refluxed for 24 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and saturated brine. The organic phase was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography to give a white solid product L4 (2.76 g, yield: 71%).

[0068] MS (EI): m / z 389.18 [M+]; Combustion-based elemental analysis: C 28 H 23 NO (%) Calculated values: C, 86.34; H, 5.95; N, 3.60; O, 4.11; Measured values: C, 86.29; H, 5.93; O, 4.14; N, 3.52.

[0069] The synthetic routes for compounds 1-20 are shown below:

[0070]

[0071] Under a nitrogen atmosphere, L4 (623 mg, 1.6 mmol), AlCl3 (748 mg, 5.6 mmol), and carbon disulfide (15 mL) were added sequentially to a 250 mL Schlenk flask. The mixture was heated to 50 °C and refluxed for 10 minutes. Then, γ-butyrolactone (327 mg, 3.8 mmol) was slowly added to the mixture over 30 minutes, and the mixture was refluxed at 50 °C for 90 minutes. After cooling to room temperature, the reaction mixture was extracted with 6 M hydrochloric acid, dried over anhydrous sodium sulfate, and the organic phase was concentrated under reduced pressure. 500 mL of water was added to the oily residue to remove γ-butyrolactone. The mixture was extracted with chloroform, and the product was converted to sodium salt by extraction of the chloroform phase with 5% sodium hydroxide solution. The aqueous solution of the sodium salt was washed with chloroform, and the mixture was acidified to pH 9-10 with concentrated hydrochloric acid. The solution was concentrated under reduced pressure to the point where water begins to distill to remove trace amounts of chloroform. The mixture was filtered through filter paper and acidified with concentrated hydrochloric acid to pH 9-10. 1-2, the lower oily layer was separated and allowed to stand to obtain crystals 1-20 (502 mg, yield: 66%).

[0072] MS (EI): m / z 475.21 [M+]; Combustion-based elemental analysis: C 32 H 29 NO3 (%) Calculated values: C, 80.82; H, 6.15; N, 2.95; O, 10.09; Measured values: C, 80.79; H, 6.08; O, 10.14; N, 2.92.

[0073] Example 3: Synthesis of compounds 1-26

[0074] The synthetic route for compound L5 is shown below:

[0075]

[0076] Under a nitrogen atmosphere, 3-phenylpropyl bromide (3.98 g, 20 mmol) and anhydrous AlCl3 (3.47 g, 26 mmol) were added to a two-necked round-bottom flask containing 45 mL of carbon disulfide solution. The reaction flask was cooled to 0 °C, and then 4-bromobenzoyl chloride (4.4 g, 20 mmol) was slowly added to the flask. The mixture was then allowed to warm naturally to room temperature and refluxed at 55 °C for 12 hours. After the reaction was complete, an ice-water solution was added to the reaction system, and the mixture was extracted with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to give a pale yellow solid product L5 (3.13 g, yield: 41%).

[0077] MS (EI): m / z 381.94 [M+]; Combustion-based elemental analysis: C 16 H 14Calculated Br2O (%): C, 50.30; H, 3.69; Br, 41.82; O, 4.19; Measured values: C, 50.26; H, 3.58; O, 4.14.

[0078] The synthetic route for compound L6 is shown below:

[0079]

[0080] Under a nitrogen atmosphere, L5 (4.6 g, 12 mmol), 10H-spiro[aziro-9,9-fluorene] (3.98 g, 12 mmol), palladium acetate (135 mg, 0.6 mmol), potassium tert-butoxide (14.4 mmol, 1.62 g), tritert-butylphosphine tetrafluoroborate (279 mg, 0.96 mmol), and anhydrous toluene (30 mL) were added sequentially to a Schlenk reaction tube. After three gas changes, the mixture was heated to 120 °C and refluxed for 24 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and saturated brine. The organic phase was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography to give a white solid product L2 (5.69 g, yield: 75%).

[0081] MS (EI): m / z 631.15 [M+]; Combustion-based elemental analysis: C 41 H 30 Calculated BrNO (%): C, 77.85; H, 4.78; Br, 12.63; N, 2.21; O, 2.53; Measured: C, 77.89; H, 4.79; O, 2.60; N, 2.24.

[0082] The synthetic routes for compounds 1-26 are shown below:

[0083]

[0084] Under a nitrogen atmosphere, L6 (1.58 g, 2.5 mmol), 5-methyl-1,3,4-thiadiazol-2-amine (432 mg, 3.75 mmol) were added sequentially to a round-bottom reaction flask. Then, triethylamine (756 mg, 7.5 mmol) and a mixture of ethanol / water (5 mL, 10:1) were slowly added. The mixture was stirred at room temperature for 3 hours. After the reaction was complete, the product was extracted with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to give a gray solid product 1-26 (1.15 g, yield: 81%).

[0085] MS (EI): m / z 568.25 [M+]; Combustion-based elemental analysis: C 41 H 32Calculated N2O (%): C, 86.59; H, 5.67; N, 4.93; O, 2.81; Measured: C, 86.52; H, 5.69; O, 2.80; N, 4.94.

[0086] Example 4: Synthesis of compounds 1-29

[0087] The synthetic route for compound L7 is shown below:

[0088]

[0089] Under a nitrogen atmosphere, 10-trimethylyl-5,10-dihydrodibenzo[b,e][1,4]azaboranecyclohexene (1.78 g, 6 mmol), L1 (2.51 g, 6 mmol), palladium acetate (68 mg, 0.3 mmol), potassium tert-butoxide (7.2 mmol, 0.81 g), tritert-butylphosphine tetrafluoroborate (139 mg, 0.48 mmol), and anhydrous toluene (26 mL) were added sequentially to the reaction flask. After three evacuations, the mixture was heated to 110 °C and refluxed for 24 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and saturated brine. The organic phase was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography to give a pale yellow solid product L7 (2.93 g, yield: 77%).

[0090] MS (EI): m / z 635.15 [M+]; Combustion-based elemental analysis: C 36 H 33 BBrNO2S (%) Calculated values: C, 68.15; H, 5.24; B, 1.70; Br, 12.59; N, 2.21; O, 5.04; S, 5.05; Measured values: C, 68.12; H, 5.29; B, 1.68; Br, 12.42; O, 5.10; N, 2.24; S, 5.11.

[0091]

[0092] Under a nitrogen atmosphere, L7 (3.29 g, 5.2 mmol), 5-methyl-1,3,4-thiadiazol-2-amine (899 mg, 7.8 mmol) were added sequentially to a round-bottom reaction flask. Then, triethylamine (1.57 g, 15.6 mmol) and a mixed solution of ethanol / water (10.5 mL, 10:1) were slowly added. The mixture was stirred at room temperature for 3 hours. After the reaction was complete, the product was extracted with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to give a gray solid product 1-29 (2.31 g, yield: 78%).

[0093] MS (EI): m / z 570.25 [M+]; Combustion-based elemental analysis: C 36 H 35 BN2O2S (%) Calculated values: C, 75.78; H, 6.18; B, 1.89; N, 4.91; O, 5.61; S, 5.62; Measured values: C, 75.80; H, 6.13; B, 1.85; N, 4.96; O, 5.66; S, 5.60.

[0094] Example 4

[0095] The self-assembled high-entropy charge-transfer luminescent material of this invention facilitates the integration of multiple functions, including efficient luminescence, energy transfer, and interface / intra-layer self-assembly. By adjusting the electron donor / acceptor intensity and end-group type, properties such as optical bandgap, exciton generation and utilization efficiency, self-assembly behavior, and carrier transport can be controlled. It can be applied to multiple functional layers and interlayer interfaces in optoelectronic devices. Optoelectronic devices include electroluminescent devices, photovoltaic devices, and photodetectors.

[0096] As an example, see reference Figure 1 One embodiment of a thin-film electroluminescent device includes, in sequence, a glass substrate 1, an anode 2 (indium tin oxide), a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 (aluminum). The self-assembled high-entropy charge-transfer luminescent material of the present invention is applied in the functional layer of the thin-film electroluminescent device. Figure 2 The electroluminescence spectrum is obtained by using the materials (compounds 1-2) of Example 1 as the light-emitting layer based on the above device structure.

[0097] The above embodiments are only used to further illustrate the self-assembled high-entropy charge-transfer luminescent material of the present invention, its preparation method and application, but the protection scope of the present invention is not limited thereto. Any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope disclosed in the present invention should be covered within the protection scope of the present invention.

Claims

1. A self-assembled high-entropy charge-transfer luminescent material, characterized in that: The device comprises an electron donor unit D, an electron acceptor unit A, and a terminal unit E. The electron donor unit D and the electron acceptor unit A form a DA configuration. The terminal unit E is connected to at least one end of the electron donor unit D and the electron acceptor unit A via an alkyl chain or an alkoxy chain. The electron donor unit D comprises aromatic amines and their derivatives, aromatic amine heterocycles and their derivatives, and the electron acceptor unit A is selected from benzophenones and their derivatives, diphenyl sulfones and their derivatives, and triazines and their derivatives. The terminal unit E is selected from phosphate groups, carboxyl groups, and amino groups.

2. The self-assembled high-entropy charge-transfer luminescent material according to claim 1, characterized in that, It has the structure shown in equation (1), equation (2), or equation (3): Wherein, n is the number of carbon atoms in the alkyl chain or alkoxy chain, ranging from 1 to 10000; in formula (Ⅲ), the E on both sides may be the same or different.

3. The self-assembled high-entropy charge-transfer luminescent material according to claim 1, characterized in that, The structure of the electron donor unit D is selected from: Wherein, X is selected from oxygen atom, sulfur atom, selenium atom, C1-10 alkyl or aryl substituted tertiary amino group, 13-20 membered heterocyclic group, substituted or unsubstituted -B(C 6-20 Aryl)-、-B(C 5-25 One of the heteroaryl groups; Y and Y' are each independently selected from hydrogen atoms, halogens, and C. 6-20 Aryl, C 5-25 One of the heteroaryl groups; dashed lines indicate whether the lines are connected or disconnected.

4. The self-assembled high-entropy charge-transfer luminescent material according to claim 1, characterized in that, The structure of the electron acceptor unit A is selected from: Wherein, Z is selected from oxygen atom, sulfur atom, selenium atom, C1-10 alkyl or aryl substituted tertiary amino group, 13-20 membered heterocyclic group, spirocyclic group, substituted or unsubstituted -B(C 6-20 Aryl)-、-B(C 5-25 One of the polyarylene groups; dashed line ----- indicates connection or disconnection.

5. The self-assembled high-entropy charge-transfer luminescent material according to claim 1, characterized in that: The electron donor unit D and the electron acceptor unit A are directly connected, conjugately bridged, non-conjugately bridged, or spatially twisted connected.

6. The self-assembled high-entropy charge-transfer luminescent material according to claim 1, characterized in that, It has the following structure:

7. A method for preparing a self-assembled high-entropy charge-transfer luminescent material according to any one of claims 1 to 6, characterized in that, Includes the following steps: Synthesize intermediates containing DA structures; An end group E, connected by an alkyl chain or alkoxy chain, is formed at at least one end of the electron donor unit D or electron acceptor unit A of the intermediate through a substitution reaction or grafting reaction.

8. The method for preparing the self-assembled high-entropy charge-transfer luminescent material according to claim 7, characterized in that, Includes the following steps: 1) 4-Bromobenzenesulfonyl chloride or 4-bromobenzoyl chloride is reacted with 3-phenylpropyl bromide to obtain a derivative based on diphenyl sulfone or benzophenone as an intermediate containing the A structure, wherein the benzene ring is connected to the bromine atom at the end of the carbon chain; 2) React an intermediate containing structure A with a compound containing structure D to synthesize an intermediate containing structure DA; 3) Replace the bromine atom at the end of the carbon chain of the intermediate containing the DA structure with the end unit E to obtain the self-assembled high-entropy charge-transfer luminescent material.

9. An optoelectronic device, characterized in that: The self-assembled high-entropy charge-transfer luminescent material as described in any one of claims 1 to 6.

10. The optoelectronic device according to claim 9, characterized in that: The optoelectronic devices include electroluminescent devices, photovoltaic devices, and photodetectors.