Pure organic room-temperature long-afterglow doped material and preparation method thereof

Abstract

The invention relates to the technical field of organic afterglow materials, and discloses a pure organic room-temperature long-afterglow doped material and a preparation method thereof. The material comprises an object phosphorescent element and a subject powder matrix, benzophenone is used as a subject, benzophenone derivatives containing benzocarbazole are used as an object, and the subject-object eutectic compound is prepared through coprecipitation. According to the present invention, the room temperature phosphorescence phenomenon observed by naked eyes can be identified by using the different phosphorescence lifetime represented by different guest molecules in the host-guest eutectic compound, such that the idea is provided for information storage and encryption.

Description

Technical Field

[0001] This invention relates to the field of organic afterglow materials technology, and in particular to a pure organic room temperature long afterglow doped material and its preparation method.

[0002] Technical terms: BPBCz refers to 4-(7H-benzo[c]carbazole-7-yl)benzophenone, BPBrBCz refers to 4-(10-bromo-7H-benzo[c]carbazole-7-yl)benzophenone, BP refers to benzophenone, BP-F refers to p-fluorobenzophenone, BP-Cl refers to p-chlorobenzophenone, BP-Br refers to p-bromobenzophenone, PE refers to petroleum ether, and EA refers to ethyl acetate. Background Technology

[0003] Long-afterglow luminescent materials are special photoluminescent materials that continue to emit light even after the excitation source is removed. These materials have broad application prospects in fields such as optical recording, emergency lighting, traffic signs, anti-counterfeiting, bioimaging, and photodynamic therapy.

[0004] Long-afterglow luminescent materials can be broadly classified into two categories based on their composition: inorganic and organic. Inorganic long-afterglow luminescent materials possess excellent properties such as strong, stable, and long-lasting luminescence; however, their synthesis requires stringent conditions, raw materials are scarce, and the control over their photoelectric properties is limited, making it difficult to meet the vast market demand and the needs of sustainable development. In contrast, organic long-afterglow luminescent materials offer advantages such as strong molecular designability, low cost, good dispersibility, biocompatibility, and good conductivity, resulting in broader application prospects and increasing attention.

[0005] Because the research and development of organic long-afterglow materials started relatively late, their types remain very limited. Therefore, designing and synthesizing efficient organic long-afterglow materials remains one of the challenges in the field of optoelectronic materials. In recent years, room-temperature phosphorescence of guest molecules activated by host-guest doping strategies has attracted much attention. However, the mechanism for extending the long-afterglow phenomenon through host-guest doping strategies still faces significant challenges, such as the unclear mechanism for regulating phosphorescence lifetime. Summary of the Invention

[0006] The first aspect of the present invention is to provide a pure organic room temperature long afterglow doped material, comprising a guest phosphorescent unit and a host powder matrix;

[0007] The guest phosphorescent unit is a benzophenone derivative containing a benzocarbazole unit;

[0008] The main powder matrix includes benzophenone or benzophenone substitutes.

[0009] This invention incorporates the BP (benzophenone) unit into the design of guest molecules from phosphorescent benzo[a]carbazole derivatives. This allows for better transfer of the triplet energy of the host BP unit to the guest molecule, thereby activating its room-temperature phosphorescence. From a molecular structure design perspective, this increases the intersystem crossing (ISC) efficiency of the guest molecule while suppressing its nonradiative transitions, thus modulating the luminescence intensity.

[0010] Preferably, the benzo[c]carbazole-containing benzophenone derivative comprises: 4-(7H-benzo[c]carbazole-7-yl)benzophenone, and / or 4-(10-bromo-7H-benzo[c]carbazole-7-yl)benzophenone.

[0011] Preferably, the benzophenone substitute includes at least one of p-fluorobenzophenone, p-chlorobenzophenone, and p-bromobenzophenone.

[0012] Preferably, the molar ratio of the guest phosphorescent unit to the host powder matrix is ​​0.5-1.5:100.

[0013] Preferably, the excitation wavelength of the pure organic room temperature long afterglow doped material is 360-380 nm.

[0014] A second aspect of this invention provides a method for preparing a pure organic room-temperature long afterglow doped material, comprising the following steps:

[0015] S1. Synthesis of guest phosphorescent unit: Under nitrogen protection, 7H-benzo[c]carbazole or 7H-benzo[c]carbazole substituted product, p-fluorobenzophenone, catalyst and solvent are added. The reaction is stirred at 70-90℃ for 8-15h. After the reaction is completed, the reaction is quenched with cold water. The product is washed and subjected to column chromatography or without column chromatography to obtain benzophenone derivatives containing benzo[c]carbazole as guest phosphorescent unit.

[0016] S2. Weigh the guest phosphorescent unit and the host powder matrix and dissolve them in the solvent respectively. Then mix them evenly and let them stand at room temperature until the solvent completely evaporates to obtain a pure organic room temperature long afterglow doped material.

[0017] This invention successfully constructed a pure organic room-temperature long-afterglow doped material by co-precipitating a benzo[c]carbazole-containing benzophenone derivative guest phosphorescent unit into a benzophenone derivative host matrix. This invention achieves significant control over phosphorescence lifetime through a simple synthesis method, resulting in a noticeably different afterglow duration. From a molecular structure design perspective, it increases the intersystem crossing (ISC) efficiency of the guest molecule while suppressing its nonradiative transitions. Introducing heavy atoms, such as Br and I, into the guest molecule enhances the ISC, thereby increasing the concentration of triplet excitons and controlling the luminescence intensity. This invention investigates the effect of heavy atom introduction into the phosphorescent unit (7H-benzo[c]carbazole group) to regulate the phosphorescence lifetime of the doped system.

[0018] Preferably, in step S1, the molar ratio of 7H-benzo[c]carbazole or 7H-benzo[c]carbazole substituted product, p-fluorobenzophenone, and catalyst is 3-5:3-5:4-8.

[0019] Preferably, in step S1, the catalyst includes at least one of potassium tert-butoxide and sodium hydride;

[0020] Preferably, in step S1, the solvent includes at least one of N,N-dimethylformamide, dimethylacetamide, diethylformamide, and dioxane.

[0021] Preferably, in step S1, the reagent used to wash the product includes at least one of ethanol, ethyl acetate, and petroleum ether.

[0022] Preferably, in step S1, the solvent used for column chromatography is a mixture of petroleum ether and ethyl acetate in a volume ratio of 4-6:1.

[0023] Preferably, in step S2, the solvent includes at least one of dichloromethane, ethyl acetate, and tetrahydrofuran.

[0024] A third aspect of the present invention is to provide an application of a pure organic room-temperature long afterglow doped material in information storage or data encryption.

[0025] Compared with the prior art, the present invention can achieve the following beneficial effects:

[0026] 1. This invention introduces the BP (benzophenone) unit into the design of guest molecules from the phosphorescent unit benzocarbazole derivative, which can better transfer the triplet energy of the host BP to the guest molecule, thereby activating the room temperature phosphorescence of the guest molecule.

[0027] 2. This invention successfully constructed a pure organic room-temperature long-afterglow doped material by co-precipitating a benzo[c]carbazole-containing benzophenone derivative guest phosphorescent unit into a benzophenone derivative host matrix. This invention achieves significant regulation of phosphorescence lifetime through a simple synthesis method, effectively extending the afterglow time to over 2 seconds, with a measured maximum lifetime of 797 ms, nearly a thousand times longer than the triphenylamine system. From a molecular structure design perspective, the intersystem crossing (ISC) efficiency of the guest molecule is increased while its non-radiative transitions are suppressed. Introducing heavy atoms, such as Br and I, into the guest molecule enhances ISC, thereby increasing the concentration of triplet excitons and regulating luminescence intensity. This invention investigates the regulation of phosphorescence lifetime in the doped system by introducing heavy atoms into the phosphorescent unit (7H-benzo[c]carbazole group). Attached Figure Description

[0028] Figure 1This is a schematic diagram of the proton nuclear magnetic resonance spectrum of BPBCz according to the present invention;

[0029] Figure 2 This is a schematic diagram of the carbon NMR spectrum of BPBCz according to the present invention;

[0030] Figure 3 This is a schematic diagram of the proton nuclear magnetic resonance spectrum of BPBrBCz according to the present invention;

[0031] Figure 4 This is a schematic diagram of the carbon NMR spectrum of BPBrBCz according to the present invention;

[0032] Figure 5 (a) Photoluminescence and phosphorescence spectra of BPBCz and BPBrBCz of the present invention; (excitation wavelength 365nm) (b) Attenuation curves of BPBCz and BPBrBCz of the present invention at 454nm;

[0033] Figure 6 The following are the fluorescence and phosphorescence spectra of the 1% mol doped powder of the present invention: Figure (a) is the fluorescence spectrum of BPBCz@BP-X (X = H, F, Cl, Br); Figure (b) is the phosphorescence spectrum of BPBCz@BP-X (X = H, F, Cl, Br); Figure (c) is the fluorescence spectrum of BPBrBCz@BP-X (X = H, F, Cl, Br); and Figure (d) is the phosphorescence spectrum of BPBrPBCz@BP-X (X = H, F, Cl, Br).

[0034] Figure 7 This is a schematic diagram of the luminescence of the doped powder of the present invention;

[0035] Figure 8 This is a schematic diagram of the decay curve of 1 mol% BPBCz@BP-X (X = H, F, Cl, Br) powder of the present invention;

[0036] Figure 9 This is a schematic diagram of the decay curve of 1 mol% BPBrBCz@BP-X (X = H, F, Cl, Br) powder of the present invention;

[0037] Figure 10 This is a schematic diagram of the decay curves of 0.01 and 0.1 mol% BPBCz@BP-X (X = H, F, Cl, Br) powders of the present invention. Detailed Implementation

[0038] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. 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.

[0039] The instruments, equipment, and chemical reagents used in the preferred embodiments of this invention are all commercially available.

[0040] A preferred embodiment of the present invention provides a pure organic room-temperature long-afterglow doped material, comprising a guest phosphorescent unit and a host powder matrix, wherein the molar ratio of the guest phosphorescent unit to the host powder matrix is ​​0.5-1.5:100. The guest phosphorescent unit is a benzo[c]carbazole-7-yl)benzophenone derivative, including 4-(7H-benzo[c]carbazole-7-yl)benzophenone and / or 4-(10-bromo-7H-benzo[c]carbazole-7-yl)benzophenone; the host powder matrix comprises at least one of benzophenone, p-fluorobenzophenone, p-chlorobenzophenone, and p-bromobenzophenone. The excitation wavelength of this pure organic room-temperature long-afterglow doped material is 360-380 nm.

[0041] The preparation method of this pure organic room temperature long afterglow doped material includes the following steps:

[0042] S1. Synthesis of the guest phosphorescent unit: Under nitrogen protection, 7H-benzo[c]carbazole or a 7H-benzo[c]carbazole substituted product, p-fluorobenzophenone, catalyst and solvent were added. The reaction was stirred at 70-90℃ for 8-15 h. After the reaction was completed, the reaction was quenched with cold water. The product was washed with ethanol and subjected to column chromatography to obtain a benzophenone derivative containing benzo[c]carbazole as the guest phosphorescent unit. The molar ratio of 7H-benzo[c]carbazole or a 7H-benzo[c]carbazole substituted product, p-fluorobenzophenone and catalyst was 3-5:3-5:4-8. The catalyst included at least one of potassium tert-butoxide. The solvent included at least one of N,N-dimethylformamide, dimethylacetamide, diethylformamide and dioxane. The solvent used for column chromatography was a mixture of petroleum ether and ethyl acetate in a volume ratio of 3-6:1.

[0043] S2. Weigh the guest phosphorescent unit and the host powder matrix and dissolve them in a solvent, including at least one of dichloromethane, trichloromethane, ethyl acetate, acetone, and tetrahydrofuran; then mix them evenly and let them stand at room temperature until the solvent completely evaporates to obtain a pure organic room temperature long afterglow doped material.

[0044] The following are specific examples.

[0045] Example 1

[0046] A pure organic room temperature long afterglow doped material includes a guest phosphorescent unit BPBCz and a host powder matrix BP, wherein the molar ratio of BPBCz to BP is 1:100.

[0047] The preparation method of this pure organic room temperature long afterglow doped material includes the following steps:

[0048] Synthesis of S1 and BPBCz: Under nitrogen protection, 7H-benzo[c]carbazole (2 mmol), p-fluorobenzophenone (2 mmol), potassium tert-butoxide catalyst (3 mmol), and DMF (10 mL) were added. The mixture was stirred at 80 °C for 12 h. After the reaction was completed, the reaction was quenched with cold water. The product was washed with ethanol and obtained by column chromatography (PE:EA = 5:1) to yield BPBCz. The synthetic route is as follows:

[0049]

[0050] 1 H NMR (400MHz, CD3Cl) δ8.90(d,J=8.3Hz,1H),8.72–8.67(m,1H),8.15(d,J=8.4Hz,2H),8.07(d,J=8.1Hz,1H),7.97(d,J=6.9Hz,2H), 7.92(d,J=8.9Hz,1H),7.80(d,J=8.4Hz,3H),7.72–7.67(m,2H),7.67–7.63(m,1H),7.58(dt,J=16.3,8.0Hz,3H),7.54–7.48(m,2H).

[0051] 13 C NMR (101MHz, CDCl3) δ195.56,140.70,138.66,138.36,137.30,137.02,132.87,131.98,130.12,129.76,129.59,129.41, 128.58,127.60,127.47,127.14,125.96,124.82,123.87,123.21,115.21,114.22,111.70,111.39,77.39,77.07,76.75.

[0052] S2. Weigh approximately 3 mg of BPBCz and BP at a molar ratio of 100 times that of BPBCz. Dissolve both in 2 ml and 3 ml of dichloromethane solvent, respectively, to obtain BPBCz solution and BP solution. After complete dissolution, mix the two solutions and allow them to stand at room temperature until the solvent has completely evaporated, yielding a pure organic room-temperature long afterglow doped material, 1% mol BPBCz@BP. Its phosphorescence lifetime was measured to be 428 ms.

[0053] Example 2

[0054] The main powder was BP-F, and the rest was the same as in Example 1. A pure organic room temperature long afterglow doped material of 1% mol BPBCz@BP-F was obtained. Its phosphorescence lifetime was measured to be 212 ms.

[0055] Example 3

[0056] The main powder was BP-Cl, and the rest was the same as in Example 1. A pure organic room-temperature long-afterglow doped material of 1% mol BPBCz@BP-Cl was obtained. Its phosphorescence lifetime was measured to be 797 ms.

[0057] Example 4

[0058] The main powder was BP-Br, and the rest was the same as in Example 1. A pure organic room-temperature long-afterglow doped material of 1% mol BPBCz@BP-Br was obtained. Its phosphorescence lifetime was measured to be 285 ms.

[0059] Example 5

[0060] A pure organic room temperature long afterglow doped material, comprising a guest phosphorescent unit BPBrBCz and a host powder matrix BP;

[0061] The preparation method of this pure organic room temperature long afterglow doped material includes the following steps:

[0062] Synthesis of S1 and BPBrBCz: Under nitrogen protection, 10-Br-7H benzo[c]carbazole (2 mmol), p-fluorobenzophenone (2 mmol), potassium tert-butoxide catalyst (3 mmol), and DMF (10 ml) were added. The mixture was stirred at 80 °C for 12 h. After the reaction was completed, the reaction was quenched with cold water. The product was washed with ethyl acetate to obtain BPBrBCz. The synthetic route is as follows:

[0063]

[0064] 1 H NMR (400MHz, CD3Cl) δ8.78(d,J=9.8Hz,2H),8.15(d,J=8.2Hz,2H),8.06(d,J=8.1Hz,1H),8.00–7.90(m,3H),7.81(t,J=7.6Hz ,1H),7.76(d,J=8.2Hz,2H),7.70(t,J=7.4Hz,1H),7.66(d,J=9.0Hz,1H),7.59(dt,J=9.1,7.3Hz,4H),7.50(d,J=8.7Hz,1H).

[0065] 13C NMR (101MHz, CDCl3) δ195.56,140.70,138.66,138.36,137.30,137.02,132.87,131.98,130.12,129.76,129.59,129.41, 128.58,127.60,127.47,127.14,125.96,124.82,123.87,123.21,115.21,114.22,111.70,111.39,77.39,77.07,76.75.

[0066] S2. Weigh approximately 3 mg of BPBrBCz and BP at a molar ratio of 100 times the weighed BPBrBCz. Dissolve both in 2 ml and 3 ml of dichloromethane solvent, respectively, to obtain BPBrBCz solution and BP solution. After complete dissolution, mix the two solutions and allow them to stand at room temperature until the solvent has completely evaporated, yielding a pure organic room-temperature long afterglow doped material, 1% mol BPBrBCz@BP. Its phosphorescence lifetime was measured to be 592 ms.

[0067] Example 6

[0068] The main powder was BP-F, and the rest was the same as in Example 5. A pure organic room temperature long afterglow doped material of 1% mol BPBrBCz@BP-F was obtained. Its phosphorescence lifetime was measured to be 77 ms.

[0069] Example 7

[0070] The main powder was BP-Cl, and the rest was the same as in Example 5. A pure organic room-temperature long afterglow doped material of 1% mol BPBrBCz@BP-Cl was obtained. Its phosphorescence lifetime was measured to be 129 ms.

[0071] Example 8

[0072] The main powder was BP-Br, and the rest was the same as in Example 5. A pure organic room temperature long afterglow doped material, 1% mol BPBrBCz@BP-Br, was obtained. Its phosphorescence lifetime was measured to be 80 ms.

[0073] Example 9

[0074] The main powder was BP, and the molar ratio of BPBrBCz to BP was 0.1%, with the remainder the same as in Example 5. A pure organic room-temperature long-afterglow doped material, 0.1% mol BPBrBCz@BP, was obtained. Its phosphorescence lifetime was measured to be 308 ms.

[0075] Example 10

[0076] The main powder was BP, and the molar ratio of BPBrBCz to BP was 0.01%, with the remainder the same as in Example 5. A pure organic room-temperature long-afterglow doped material of 0.01% mol BPBrBCz@BP was obtained. Its phosphorescence lifetime was measured to be 316 ms.

[0077] The following are characterization tests.

[0078] Figure 1-4 The figures show the 1H and 1C NMR spectra of BPBCz and BPBrBCz. As can be seen from the figures, this invention successfully synthesized BPBCz and BPBrBCz materials.

[0079] Figure 5 The photoluminescence and phosphorescence spectra of BPBCz and BPBrBCz are shown, along with their decay kinetics at 454 nm. (The excitation wavelengths used for acquiring the spectra were 365 nm and 391 nm, respectively). Figure 5 (a) We observed fluorescence emission peaks of BPBCz and BPBrBCz solid powders at 454 nm, with BPBrBCz showing a stronger peak than BPBCz. Neither of them emitted phosphorescence. Figure 5 (b) shows the decay curves at 454 nm. The fitted lifetimes of BPBCz and BPBrBCz are 30.22 ns and 24.69 ns, respectively, corresponding to their fluorescence lifetimes. Therefore, at room temperature, BPBCz and BPBrBCz only fluoresce and are quenched by phosphorescence.

[0080] Figure 6 The photoluminescence spectra of 1% mol BPBCz@BP-X and 1% mol BPBrBCz@BP-X (X = H, F, Cl, Br) are shown in the figure. As can be seen from the figure, both the BPBCz@BP-X and BPBrBCz@BP-X (X = H, F, Cl, Br) systems exhibit phosphorescence emission bands at 508 and 513 nm, respectively. Furthermore, we found that the phosphorescence of BPBrBCz doped with BPBCz is nearly 2-3 times stronger than that of BPBCz doped with BPBCz. Spectroscopic analysis indicates that external heavy atoms prolong the afterglow of the BPBCz@BP-X system, with the afterglow duration in the order Cl > H > Br > F, and the longest afterglow time for the guest BP-Cl. For the BPBrBCz@BP-X system, the longest afterglow is achieved with BP-Br as the guest BP-Br, with the afterglow duration in the order Cl > H > Br > F. Overall, the introduction of the heavy atom Br into the guest molecule shortens the afterglow of the doped system.

[0081] Figure 7 These are photographs of the doped system before and after irradiation with 365nm ultraviolet light. Figure 7It can be seen that all doped materials exhibit strong fluorescence emission under UV light irradiation. When the UV light is turned off, a significant afterglow is observed, and the instantaneous phosphorescence of BPBrBCz@BP-X (X=H,F,Cl,Br) is stronger than that of BPBCz@BP-X (X=H,F,Cl,Br) at the moment the UV light is turned off, which is consistent with the results of instantaneous phosphorescence spectroscopy measurements. The afterglow of BPBCz@BP-X (X=H,F,Cl,Br) is significantly longer than that of BPBrBCz@BP-X (X=H,F,Cl,Br). These results indicate that we can successfully extend the afterglow time through a simple molecular design strategy, making it visible to the naked eye.

[0082] Figure 8 The decay kinetics of a 1 mol% BPBCz@BP-X (X = H, F, Cl, Br) doped system. Figure 9 The decay kinetics of a 1 mol% BPBrBCz@BP-X (X = H, F, Cl, Br) doped system. Figure 10 The decay kinetics of 0.1 mol% and 0.01 mol% BPBCz@BP-X (X = H, F, Cl, Br) doped systems were investigated. Lifetime fitting of the kinetic curves revealed that BP-Cl as the host dopant exhibited the longest lifetime. The phosphorescence lifetime of the BPBrBCz doped system was shorter than that of the BPBCz doped system. Reducing the guest doping concentration further shortened the phosphorescence lifetime, consistent with the observed afterglow duration. Therefore, the introduction of internal and external heavy atoms is an effective method for controlling the room-temperature phosphorescence properties of host-guest doped systems.

[0083] This invention utilizes the different phosphorescence lifetimes exhibited by different guest molecules in host-guest eutectic compounds to identify room-temperature phosphorescence phenomena observed by the naked eye, thereby providing ideas for information storage and encryption.

[0084] Finally, it should be noted that the above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art can still modify the technical solutions described in the foregoing embodiments or make equivalent substitutions for some of the technical features. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A pure organic room-temperature long afterglow doped material, characterized in that, Includes guest phosphorescent units and host powder matrix; The guest phosphorescent unit is a benzophenone derivative containing a benzocarbazole unit; The main powder matrix includes benzophenone or benzophenone substitutes.

2. The pure organic room-temperature long afterglow doped material according to claim 1, characterized in that, The benzo[c]carbazole-containing benzophenone derivatives include: 4-(7H-benzo[c]carbazole-7-yl)benzophenone, and / or 4-(10-bromo-7H-benzo[c]carbazole-7-yl)benzophenone.

3. The pure organic room-temperature long afterglow doped material according to claim 1, characterized in that, The benzophenone substitutes include at least one of p-fluorobenzophenone, p-chlorobenzophenone, and p-bromobenzophenone.

4. The pure organic room-temperature long afterglow doped material according to claim 1, characterized in that, The molar ratio of the guest phosphorescent unit to the host powder matrix is ​​0.5-1.5:

100.

5. The pure organic room-temperature long afterglow doped material according to claim 1, characterized in that, The excitation wavelength of the pure organic room temperature long afterglow doped material is 360-380 nm.

6. A method for preparing a pure organic room-temperature long afterglow doped material, characterized in that, Includes the following steps: S1. Synthesis of guest phosphorescent unit: Under nitrogen protection, 7H-benzo[c]carbazole or 7H-benzo[c]carbazole substituted product, p-fluorobenzophenone, catalyst and solvent were added and stirred at 80℃ for 12h. After the reaction was completed, the reaction was quenched with cold water, the product was washed, and column chromatography or without column chromatography was performed to obtain benzophenone derivatives containing benzo[c]carbazole units as guest phosphorescent units. S2. Weigh the guest phosphorescent unit and the host powder matrix and dissolve them in the solvent respectively. Then mix them evenly and let them stand at room temperature until the solvent completely evaporates to obtain a pure organic room temperature long afterglow doped material.

7. The pure organic room-temperature long afterglow doped material according to claim 1, characterized in that, In step S1, the molar ratio of 7H-benzo[c]carbazole or 7H-benzo[c]carbazole substituted product, p-fluorobenzophenone, and catalyst is 3-5:3-5:4-8.

8. The pure organic room-temperature long afterglow doped material according to claim 1, characterized in that, In step S1, the catalyst includes at least one of potassium tert-butoxide and sodium hydride; The solvent includes at least one of N,N-dimethylformamide, dimethylacetamide, diethylformamide, and dioxane; The reagents used to wash the product include at least one of ethanol, ethyl acetate, and petroleum ether; The solvent used for column chromatography is a mixture of petroleum ether and ethyl acetate in a volume ratio of 4-6:

1.

9. The pure organic room-temperature long afterglow doped material according to claim 1, characterized in that, In step S2, the solvent includes at least one of dichloromethane, ethyl acetate, and tetrahydrofuran.

10. The application of a pure organic room temperature long afterglow doped material according to any one of claims 1-9 in information storage or data encryption.

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