An organic room temperature phosphorescent material based on phenazine derivatives and its preparation and application

Abstract

The present invention relates to the technical field of luminescent materials, and particularly to an organic room temperature phosphorescent material based on phenazine derivatives and its preparation and application. In the present invention, a guest molecule G and a host molecule H are mixed by a heating melting method, a solvent evaporation crystallization method, a vapor diffusion co-crystallization method or a spin coating method to obtain an organic room temperature phosphorescent material based on phenazine derivatives; the preparation process of the present invention is simple, and the prepared organic room temperature phosphorescent material has excellent stability. After the material is placed in the air for several months, it still has excellent room temperature phosphorescent properties. The organic room temperature phosphorescent material prepared by the method of the present invention exhibits yellow to orange phosphorescence, expanding the field of organic room temperature phosphorescent materials. The raw materials used are simple and easy to obtain, and are harmless to humans and the environment.

Description

Technical Field

[0001] The present invention relates to the technical field of luminescent materials, and particularly relates to an organic room temperature phosphorescent material based on phenazine derivatives, and its preparation and application. Background Art

[0002] Dihydrodibenzophenazine derivatives are a class of typical vibration-induced emission (VIE) molecules. And VIE is a luminescence mechanism with unique photophysical properties. VIE compounds have continuously tunable multi-emission characteristics. In solution and other unconstrained states, VIE compounds mainly exhibit abnormal red light emission derived from their planar configuration, which is generated by intramolecular vibration; while in the constrained state, VIE compounds mainly exhibit intrinsic blue light emission derived from their saddle-shaped configuration. With the change of the constrained state of VIE compounds, the fluorescence of VIE compounds can be continuously tuned in the interval between intrinsic blue light emission and abnormal red light emission, and even can pass through the white light interval. Due to their environment-sensitive multi-emission properties, currently, VIE has been widely used in the fields of ratio fluorescent probes, bioimaging, and organic optoelectronics, etc., but its phosphorescent properties have rarely been studied.

[0003] Phosphorescence has a larger Stokes shift compared with fluorescence, which can avoid the interference of the excitation light. At the same time, phosphorescence also has a longer lifetime than fluorescence, which can avoid the interference of fluorescence and scattered light and achieve optical imaging with higher contrast and signal-to-noise ratio. Usually, phosphorescence requires low temperature and anaerobic conditions, which limits its application. In recent years, the developed room temperature phosphorescence system has been widely used in the fields of anti-counterfeiting, information encryption, chemical sensing, and bioimaging, etc. Therefore, developing room temperature phosphorescent materials has important significance and practical value.

[0004] However, most of the room temperature phosphorescent materials reported so far are based on inorganic materials and organometallic complexes. Inorganic room temperature phosphorescent materials are limited in variety, poor in processability, and complex and difficult to synthesize. At the same time, the application of organometallic complex room temperature phosphorescent materials is also limited to a certain extent due to their poor stability and dependence on expensive rare earth metals. In view of these problems, the development of organic room temperature phosphorescent materials is of great significance because, on the one hand, organic room temperature phosphorescent materials are widely available, have simple and adjustable structures, and are relatively low in cost. On the other hand, organic room temperature phosphorescent materials are less toxic to cells and have better biocompatibility than inorganic room temperature phosphorescent materials and metal complex room temperature phosphorescent materials, making them have greater development potential and application potential in the field of life sciences. In addition, pure organic phosphorescent materials also have better processability and can be used in flexible electronic devices. Therefore, organic room temperature phosphorescent materials have been favored by more and more researchers. The development of efficient and long-life organic room temperature phosphorescent materials is a key scientific issue that needs to be solved in the current field of organic light-emitting materials and is also a great challenge. Organic host-guest doping is an effective strategy for obtaining room-temperature phosphorescent materials developed in recent years, but there are also problems such as unsatisfactory phosphorescence quantum yield and complex synthesis. Therefore, through new doping methods, the preparation of organic room-temperature phosphorescent doped materials with high phosphorescence quantum yield, long life and long afterglow based on new guest molecules and easily available host molecules has important research significance and practical value. Summary of the invention

[0005] In order to solve the above problems, the purpose of the present invention is to provide an organic room temperature phosphorescent material based on phenazine derivatives and its preparation and application. In the present invention, the guest molecule G and the host molecule H are mixed by heating and melting method, solvent evaporation crystallization method, vapor diffusion eutectic method or spin coating method to obtain an organic room temperature phosphorescent material based on phenazine derivatives; the preparation process of the present invention is simple, and the prepared organic room temperature phosphorescent material has excellent stability. After the material is placed in the air for several months, it still has excellent room temperature phosphorescent performance. The organic room temperature phosphorescent material prepared by the method of the present invention exhibits yellow to orange phosphorescence, which expands the field of organic room temperature phosphorescent materials. The raw materials used are simple and easy to obtain and harmless to the human body and the environment.

[0006] The dihydrodibenzophenazine derivatives described in the present invention have vibration-induced luminescence characteristics and environmentally sensitive fluorescence multi-emission characteristics. The synthesis steps of the dihydrodibenzophenazine derivatives are simple. The doping process with host materials such as benzophenone (BO), triphenylamine (TPA), triphenylphosphine (TPP), and triphenylarsine (TPAs) is simple, environmentally friendly, has mild preparation conditions, is easy to control, the raw materials can be purchased at low prices, no chemical synthesis is required, and the preparation cost is low. Long afterglow organic room temperature phosphorescence can be simply prepared, which is suitable for large-scale production. At the same time, the vibration-induced luminescence characteristics, high quantum yield, and long afterglow characteristics of the prepared organic room temperature phosphorescent materials make them applicable to fields such as anti-counterfeiting, chemical and biological detection, and biological imaging.

[0007] The object of the present invention can be achieved through the following technical solutions:

[0008] The first object of the present invention is to provide an organic room temperature phosphorescent material based on phenazine derivatives, which is obtained by doping a guest molecule G and a host molecule H; the guest molecule G is selected from one of G1, G2, G3, or G4; the host molecule H is selected from one or more of H1, H2, H3, H4, or H5;

[0009]

[0010] wherein, R is selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a boric acid group, a borate group, an aldehyde group, a hydroxyl group, a pyridyl group, a vinylpyridine, a carboxyl group, an alkoxy group, an acyl group, an ester group, a cyano group, or a trifluoromethyl group; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 are each independently selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group, an alkoxy group, or an acyl group; the carbon number of the alkyl group, alkoxy group, or acyl group is 1–6.

[0011] In one embodiment of the present invention, the guest molecule G is selected from one of the following structural formulas:

[0012]

[0013] The host molecule H is selected from one or more of the following structural formulas;

[0014]

[0015]

[0016] In one embodiment of the present invention, the molar ratio of the guest molecule G to the host molecule H is 0.001-20:100.

[0017] The second object of the present invention is to provide a preparation method of an organic room temperature phosphorescent material based on phenazine derivatives, comprising the following steps:

[0018] Mix the guest molecule G and the host molecule H to obtain an organic room temperature phosphorescent material based on phenazine derivatives;

[0019] The guest molecule G is selected from one of G1, G2, G3 or G4; the host molecule H is selected from one or more of H1, H2, H3, H4 or H5;

[0020]

[0021] Wherein, R is selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a boric acid group, a borate group, an aldehyde group, a hydroxyl group, a pyridyl group, a vinylpyridine, a carboxyl group, an alkoxy group, an acyl group, an ester group, a cyano group or a trifluoromethyl group; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 are each independently selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group, an alkoxy group or an acyl group; the carbon number of the alkyl group, alkoxy group or acyl group is 1-6.

[0022] In one embodiment of the present invention, during the mixing process, the mixing method is selected from one or more of a heat melting method, a solvent evaporation crystallization method, a vapor diffusion eutectic method or a spin coating method.

[0023] In one embodiment of the present invention, the specific steps of the heat melting method are as follows:

[0024] Pre-mix the guest molecule G and the host molecule H to obtain a pre-mixture, heat the pre-mixture to complete melting and then cool it to room temperature to obtain an organic room temperature phosphorescent material based on phenazine derivatives.

[0025] In one embodiment of the present invention, the specific steps of the solvent evaporation crystallization method are as follows:

[0026] The guest molecule G and the host molecule H are premixed and then added to a good solvent. After complete dissolution, a mixed solution is obtained. The mixed solution is mixed with a poor solvent, and after evaporation of the solvent, crystallization and post-treatment, an organic room temperature phosphorescent material based on a phenazine derivative is obtained.

[0027] In one embodiment of the present invention, the good solvent is selected from one of dichloromethane or tetrahydrofuran; the poor solvent is selected from one of n-hexane or methanol.

[0028] In one embodiment of the present invention, the post-treatment is to filter and collect the filter residue.

[0029] In one embodiment of the present invention, the specific steps of the vapor diffusion eutectic method are as follows:

[0030] The guest molecule G and the host molecule H are premixed and then added to a good solvent. After complete dissolution, a mixed solution is obtained. The mixed solution is mixed with a poor solvent, sealed and placed in a cool and dry place until crystals grow, and an organic room temperature phosphorescent material based on a phenazine derivative is obtained.

[0031] In one embodiment of the present invention, the good solvent is selected from one of dichloromethane or tetrahydrofuran; the poor solvent is selected from one of n-hexane or methanol.

[0032] In one embodiment of the present invention, the specific steps of the spin coating method are as follows:

[0033] The guest molecule G and the host molecule H are premixed and then added to a good solvent. After complete dissolution, a mixed solution is obtained. The mixed solution is spin-coated on a substrate, and after post-treatment, an organic room temperature phosphorescent material based on a phenazine derivative is obtained.

[0034] In one embodiment of the present invention, the good solvent is selected from one of dichloromethane or tetrahydrofuran.

[0035] In one embodiment of the present invention, the rotation speed of the spin coating is 300 - 3000 revolutions per minute.

[0036] In one embodiment of the present invention, the post-treatment is heating annealing, the annealing time is 0.5 - 6 hours, and the annealing temperature is 40 - 240 °C.

[0037] The third object of the present invention is to provide an application of an organic room temperature phosphorescent material (long lifespan, high brightness) based on a phenazine derivative in anti-counterfeiting, information encryption, and biological imaging.

[0038] The organic room temperature phosphorescent material based on a phenazine derivative provided by the present invention has continuously adjustable luminescent properties, long lifespan, high quantum yield, and low cost, and thus can be well applied in anti-counterfeiting, information encryption, chemical sensing, and biological imaging.

[0039] The organic room-temperature phosphorescent materials based on phenazine derivatives prepared by the preparation method provided by the present invention emit strong yellow or even orange long-afterglow phosphorescence with different phosphorescence lifetimes. The host molecules used to prepare the organic room-temperature phosphorescent materials based on phenazine derivatives all exhibit blue-violet fluorescence, the guest molecules emit strong sky-blue, green or yellow fluorescence in the solid state, and the doping system emits blue light, orange light or white light under ultraviolet light. Therefore, the organic room-temperature phosphorescent materials based on phenazine obtained in the present invention and the guest molecule phenazine derivatives together can be used to prepare patterns with anti-counterfeiting functions. By controlling the on and off of the ultraviolet lamp, the change of temperature, the doping concentration, etc., different colors of patterns and information can be presented, so the applications in anti-counterfeiting and information encryption can be realized.

[0040] The luminescence properties of the organic room-temperature phosphorescent materials based on phenazine derivatives prepared by the preparation method provided by the present invention are affected by temperature, humidity, oxygen concentration, solvent atmosphere, etc., and thus can be used for the detection and sensing of temperature, humidity, oxygen and volatile organic compounds.

[0041] The organic room-temperature phosphorescent materials based on phenazine derivatives prepared by the preparation method provided by the present invention can be applied to bioimaging by virtue of their long lifetime, high brightness and long-wavelength emission.

[0042] Compared with the prior art, the present invention has the following beneficial effects:

[0043] (1) The organic room-temperature phosphorescent materials based on phenazine derivatives provided by the present invention can all produce obvious sky-blue fluorescence under ultraviolet light irradiation, and can produce visible yellow to orange phosphorescence after turning off the ultraviolet light. The phosphorescence quantum yield can reach 4.8–13.3%, and the phosphorescence lifetime can reach 145–375 ms;

[0044] (2) For the organic room-temperature phosphorescent materials based on phenazine derivatives provided by the present invention, both the host and guest molecules are non-toxic, harmless, simple and easy to obtain. The host molecule has a low cost, the guest molecule is simple to prepare, does not require complex molecular design, is easy to realize industrial production, and has good practical application value;

[0045] (3) The preparation process of the organic room-temperature phosphorescent materials based on phenazine derivatives provided by the present invention is simple, and the prepared organic room-temperature phosphorescent materials have excellent stability. After the materials are placed in the air for several months, they still have excellent room-temperature phosphorescent properties. The organic room-temperature phosphorescent materials prepared according to the method of the present invention exhibit yellow to orange phosphorescence, expanding the field of organic room-temperature phosphorescent materials. The raw materials used are simple and easy to obtain, and are harmless to humans and the environment;

[0046] (4) The organic room temperature phosphorescent material based on phenazine derivatives provided by the present invention has different phosphorescence and fluorescence emission peaks, with different intensities and lifetimes, for the composite materials obtained by doping the same guest with different host molecules. Moreover, the fluorescence emission and phosphorescence emission of the composite materials obtained by doping different guest molecules with the same host molecule are also different, and it can be applied to fields such as multiple high-level anti-counterfeiting, dynamic information encryption, information display, chemical sensing, and bioimaging. Description of the Drawings

[0047] Figure 1 Schematic diagram of the afterglow of the organic room temperature phosphorescent materials based on phenazine derivatives prepared in Example 1, Example 3, Example 5, and Example 7;

[0048] Figure 2 Fluorescence spectrum, phosphorescence spectrum, full photoluminescence spectrum, and phosphorescence lifetime spectrum of the organic room temperature phosphorescent material G(1)+H(1) based on phenazine derivatives prepared in Example 1 at room temperature;

[0049] Figure 3 Fluorescence spectrum, phosphorescence spectrum, full photoluminescence spectrum, and phosphorescence lifetime spectrum of the organic room temperature phosphorescent material G(3)+H(1) based on phenazine derivatives prepared in Example 2 at room temperature;

[0050] Figure 4 Fluorescence spectrum, phosphorescence spectrum, full photoluminescence spectrum, and phosphorescence lifetime spectrum of the organic room temperature phosphorescent material G(1)+H(3) based on phenazine derivatives prepared in Example 3 at room temperature;

[0051] Figure 5 Fluorescence spectrum, phosphorescence spectrum, full photoluminescence spectrum, and phosphorescence lifetime spectrum of the organic room temperature phosphorescent material G(3)+H(3) based on phenazine derivatives prepared in Example 4 at room temperature;

[0052] Figure 6 Fluorescence spectrum, phosphorescence spectrum, full photoluminescence spectrum, and phosphorescence lifetime spectrum of the organic room temperature phosphorescent material G(1)+H(4) based on phenazine derivatives prepared in Example 5 at room temperature;

[0053] Figure 7 Fluorescence spectrum, phosphorescence spectrum, full photoluminescence spectrum, and phosphorescence lifetime spectrum of the organic room temperature phosphorescent material G(3)+H(4) based on phenazine derivatives prepared in Example 6 at room temperature;

[0054] Figure 8 Fluorescence spectrum, phosphorescence spectrum, full photoluminescence spectrum, and phosphorescence lifetime spectrum of the organic room temperature phosphorescent material G(1)+H(5) based on phenazine derivatives prepared in Example 7 at room temperature;

[0055] Figure 9Fluorescence spectrum, phosphorescence spectrum, photoluminescence full spectrum and phosphorescence lifetime spectrum of the phenazine derivative-based organic room temperature phosphorescent material G(3)+H(5) prepared in Example 8 at room temperature. Detailed implementation mode

[0056] The present invention provides an organic room temperature phosphorescent material based on a phenazine derivative, which is obtained by doping a guest molecule G and a host molecule H; the guest molecule G is selected from one of G1, G2, G3 or G4; the host molecule H is selected from one or more of H1, H2, H3, H4 or H5;

[0057]

[0058]

[0059] Among them, R is selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a boric acid group, a borate group, an aldehyde group, a hydroxyl group, a pyridyl group, a vinylpyridine, a carboxyl group, an alkoxy group, an acyl group, an ester group, a cyano group or a trifluoromethyl group; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 are each independently selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group, an alkoxy group or an acyl group; the number of carbon atoms of the alkyl group, alkoxy group or acyl group is 1-6.

[0060] In one embodiment of the present invention, the guest molecule G is selected from one of the following structural formulas:

[0061]

[0062] The host molecule H is selected from one or more of the following structural formulas;

[0063]

[0064]

[0065] In one embodiment of the present invention, the molar ratio of the guest molecule G to the host molecule H is 0.001-20:100.

[0066] The present invention provides a preparation method of an organic room temperature phosphorescent material based on a phenazine derivative, comprising the following steps:

[0067] Mix the guest molecule G and the host molecule H to obtain an organic room temperature phosphorescent material based on a phenazine derivative;

[0068] The guest molecule G is selected from one of G1, G2, G3 or G4; the host molecule H is selected from one or more of H1, H2, H3, H4 or H5;

[0069]

[0070] Among them, R is selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a boronic acid group, a borate group, an aldehyde group, a hydroxyl group, a pyridyl group, a vinylpyridine, a carboxyl group, an alkoxy group, an acyl group, an ester group, a cyano group or a trifluoromethyl group; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 are each independently selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group, an alkoxy group or an acyl group; the alkyl group, alkoxy group or acyl group has 1-6 carbon atoms.

[0071] In one embodiment of the present invention, during the mixing process, the mixing method is selected from one or more of a heat melting method, a solvent evaporation crystallization method, a vapor diffusion eutectic method or a spin coating method.

[0072] In one embodiment of the present invention, the specific steps of the heat melting method are as follows:

[0073] Pre-mix the guest molecule G and the host molecule H to obtain a pre-mixture, heat the pre-mixture until it is completely melted and then cool it to room temperature to obtain an organic room temperature phosphorescent material based on a phenazine derivative.

[0074] In one embodiment of the present invention, the specific steps of the solvent evaporation crystallization method are as follows:

[0075] Add a good solvent after pre-mixing the guest molecule G and the host molecule H, and after complete dissolution, obtain a mixed solution; mix the mixed solution with a poor solvent, evaporate the solvent, crystallize and then perform post-treatment to obtain an organic room temperature phosphorescent material based on a phenazine derivative.

[0076] In one embodiment of the present invention, the good solvent is selected from one of dichloromethane or tetrahydrofuran; the poor solvent is selected from one of n-hexane or methanol.

[0077] In one embodiment of the present invention, the post-treatment is filtration to obtain filter residue.

[0078] In one embodiment of the present invention, the specific steps of the vapor diffusion eutectic method are as follows:

[0079] Pre-mix the guest molecule G and the host molecule H, then add a good solvent and completely dissolve to obtain a mixed solution; mix the mixed solution with a poor solvent, seal it and place it in a cool and dry place until crystals grow, thus obtaining an organic room temperature phosphorescent material based on phenazine derivatives.

[0080] In one embodiment of the present invention, the good solvent is selected from one of dichloromethane or tetrahydrofuran; the poor solvent is selected from one of n-hexane or methanol.

[0081] In one embodiment of the present invention, the specific steps of the spin coating method are as follows:

[0082] Pre-mix the guest molecule G and the host molecule H, then add a good solvent and completely dissolve to obtain a mixed solution; spin coat the mixed solution on a substrate, and perform post-treatment to obtain an organic room temperature phosphorescent material based on phenazine derivatives.

[0083] In one embodiment of the present invention, the good solvent is selected from one of dichloromethane or tetrahydrofuran.

[0084] In one embodiment of the present invention, the rotation speed of the spin coating is 300 - 3000 revolutions per minute.

[0085] In one embodiment of the present invention, the post-treatment is heating annealing, the annealing time is 0.5 - 6 hours, and the temperature of the annealing treatment is 40 - 240 °C.

[0086] The present invention provides an application of an organic room temperature phosphorescent material based on phenazine derivatives in anti-counterfeiting, information encryption and biological imaging.

[0087] The present invention will be described in detail below with reference to the accompanying drawings and specific embodiments.

[0088] In the following examples, unless otherwise specified, the reagents used are commercially available reagents; the detection means and methods used are conventional detection means and methods in the art.

[0089] In the following examples, the chemical structural formula of the guest molecule G(1) is shown as follows:

[0090]

[0091] Its specific preparation method and preparation process are as follows:

[0092]

[0093] Add N to a 100 mL round-bottom flask 9 ,N 10 -bis(phenyl)phenanthrene-9,10-diamine (1500 mg, 4.17 mmol), potassium carbonate (748 mg, 5.41 mmol), copper(I) trifluoromethanesulfonate (377 mg, 1.04 mmol) and mesitylene (20.00 g). Stir the mixture in an air atmosphere at 180 °C for 2 hours. Then add iodobenzene (2.32 mL, 20.82 mmol) to the flask and raise the temperature to 215 °C and continue the reaction for 6 hours. After the reaction is completed, cool the reaction mixture to room temperature and remove mesitylene by distillation under reduced pressure. Then add 20 mL of dichloromethane, stir for 20 minutes, and filter to obtain a filtrate. Rotate the filtrate to remove dichloromethane to obtain a black oil. Finally, purify the product by silica gel column chromatography (eluent: petroleum ether) to obtain white solid G(1) (900 mg, 49.8%). 1 H NMR (400 MHz, CDCl 3 ) δ 8.74 (d, J = 8.3 Hz, 2H), 8.13 (d, J = 8.2 Hz, 2H), 7.75 (dd, J = 5.7, 3.5 Hz, 2H), 7.65 (t, J = 7.1 Hz, 2H), 7.55 (t, J = 7.5 Hz, 2H), 7.34 (dd, J = 5.9, 3.5 Hz, 2H), 7.09–6.89 (m, 8H), 6.79 (t, J = 6.9 Hz, 2H).

[0094] The chemical structural formula of the guest molecule G(2) is shown as follows

[0095]

[0096] The specific preparation method and process are as follows

[0097]

[0098] Add N to a 100 mL round-bottom flask 9 ,N 10-Bis(phenyl)phenanthrene-9,10-diamine (1500 mg, 4.17 mmol), potassium carbonate (748 mg, 5.41 mmol), copper(I) trifluoromethanesulfonate (377 mg, 1.04 mmol) and mesitylene (20 g) were placed in an air atmosphere and stirred at 180 °C for 2 h. Subsequently, p-bromoiodobenzene (5868 mg, 20.82 mmol) was added to the flask, and the temperature was raised to 215 °C and the reaction was continued for 6 h. After the reaction was completed, it was cooled to room temperature, and mesitylene was removed by distillation under reduced pressure. Then 20 mL of dichloromethane was added, and the mixture was stirred for 20 min and filtered to obtain a filtrate. The filtrate was rotary evaporated to remove dichloromethane to obtain a black oil. Finally, it was purified by silica gel column chromatography (eluent: petroleum ether) to obtain a yellow-green solid G(2) (960 mg, 45.0%). 1 H NMR (DMSO-d 6 , 400 MHz), δ: 8.95 (d, J = 8.4 Hz, 2H), 7.93–7.98 (m, 3H), 7.88–7.91 (m, 1H), 7.59–7.76 (m, 4H), 7.43–7.46 (m, 2H), 7.22 (d, J = 9.2 Hz, 2H), 7.07–7.12 (m, 2H), 7.01 (d, J = 7.6 Hz, 2H), 6.82–6.91 (m, 3H).

[0099] The chemical structural formula of the guest molecule G(3) is shown as follows

[0100]

[0101] The specific preparation method and process are as follows

[0102]

[0103] Then G(2) (1000 mg, 1.95 mmol) was added to a 100 mL round-bottom flask. Under a nitrogen atmosphere, 50 mL of ultra-dry tetrahydrofuran was added to the flask. The flask was placed in a liquid nitrogen-acetone bath, and the temperature was lowered to -78 °C. Then n-butyllithium (2.4 mL, 3.9 mmol) was added thereto, and the mixture was stirred at -78 °C for 2 h. Subsequently, trimethyl borate (1.12 mL, 9.75 mmol) was added to the flask. After 1 h, the reaction was restored to room temperature. Then HCl (3 M, 10 mL) was added to the flask, and the mixture was stirred for 2 h. After the reaction was completed, it was extracted with dichloromethane and water, and the organic phase was collected. Finally, the crude product was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate, where the volume ratio of petroleum ether to ethyl acetate is 3:1) to obtain a white solid G(3) (630 mg, 67.6%). 1 H NMR (400 MHz, CDCl 3)δ 8.80–8.66 (m, 2H), 8.07 (dd, J=19.5, 8.1 Hz, 2H), 7.82–7.45 (m, 8H), 7.41–7.29 (m, 2H), 7.05–6.86 (m, 6H), 6.82–6.64 (m, 1H).

[0104] The chemical structural formula of the guest molecule G(4) is shown as follows:

[0105]

[0106] The specific preparation method and process are as follows:

[0107]

[0108] Add G(1) (1000 mg, 2.30 mmol) and 20 mL of ultradry DMF to a 100 mL round-bottom flask. Under a nitrogen atmosphere and at 0 °C, slowly add phosphorus oxychloride (2.15 mL, 23.00 mmol) dropwise to the flask. After continuing to stir for 30 minutes, raise the temperature to 80 °C and continue the reaction for 12 hours. After the reaction is completed, cool to room temperature, pour the reaction solution into ice water, adjust the pH to 7 with sodium hydroxide solution, and then filter to obtain the filter residue. Finally, purify the filter residue by silica gel column (eluent: petroleum ether / ethyl acetate, where the volume ratio of petroleum ether to ethyl acetate is 4:1) to obtain the yellow solid G(4) (478 mg, 45.3%). 1 H NMR (400 MHz, DMSO-d6): δ 9.69 (s, 1H), 8.99 (dd, J 1 =8.3 Hz, J 2 =3.3 Hz, 2H), 8.03 (dd, J 1 =6.0 Hz, J 2 =3.4 Hz, 1H), 7.99–7.94 (m, 3H), 7.80–7.68 (m, 3H), 7.63 (dd, J 1 =12.4 Hz, J 2 =8.2 Hz, 3H), 7.53–7.47 (m, 2H), 7.11–7.00 (m, 6H), 6.84 (t, J=6.9 Hz, 1H).

[0109] The chemical structural formula of the guest molecule G(5) is shown as follows:

[0110]

[0111] The specific preparation method and process are as follows:

[0112]

[0113] Add G(2) (500 mg, 0.98 mmol), 4-pyridineboronic acid (360 mg, 2.93 mmol), potassium carbonate (1935 mg, 14.00 mmol), tetrakis(triphenylphosphine)palladium (56 mg, 0.05 mmol), 28 mL of tetrahydrofuran and 7 mL of water to a 100 mL two-necked flask. Under a nitrogen atmosphere, heat to 80 °C and reflux for 12 h. Subsequently, after the flask is cooled to room temperature, the mixed solution is extracted three times with dichloromethane and water to obtain a black oil. Finally, it is purified by silica gel column (eluent: petroleum ether / ethyl acetate, where the volume ratio of petroleum ether to ethyl acetate is 4:1) to obtain a pale green solid G(5) (250 mg, yield: 50%). 1 HNMR(400MHz,CDCl 3 )δ8.76(dd,J=8.3,3.4Hz,2H),8.51(s,2H),8.11(d,J=8.2Hz,2H),7.84–7.73(m,2H),7.68(td,J=8.1,1.2Hz,2H),7.62–7.51(m,2H),7.43–7.29(m,6H),7.08–6.97(m,6H),6.82–6.74(m,1H).

[0114] The chemical structural formula of the guest molecule G(6) is shown as follows

[0115]

[0116] The specific preparation method and process are as follows

[0117]

[0118] Add G(2) (500 mg, 0.98 mmol), 4-vinylpyridine (0.21 mL, 1.95 mmol), potassium carbonate (163 mg, 1.18 mmol), palladium acetate (22 mg, 0.098 mmol) and 40 mL of DMF to a 100 mL two-necked flask. Under a nitrogen atmosphere, heat to 160 °C and reflux for 24 h. Subsequently, after the flask is cooled to room temperature, the DMF is removed by rotary evaporation, and then it is extracted three times with dichloromethane and water to obtain a black oil. Finally, it is purified by silica gel column (eluent: petroleum ether / ethyl acetate, where the volume ratio of petroleum ether to ethyl acetate is 2:1) to obtain a pale yellow solid G(6) (303 mg, yield: 57.8%). 1 H NMR(400MHz,DMSO-d 6)δ 8.96 (d, J = 8.2 Hz, 2H), 8.47 (d, J = 5.7 Hz, 2H), 8.02–7.89 (m, 4H), 7.78–7.68 (m, 2H), 7.63 (dd, J = 16.0, 8.1 Hz, 2H), 7.49–7.40 (m, 4H), 7.35 (dd, J = 12.6, 7.9 Hz, 3H), 7.13–6.90 (m, 7H), 6.82 (t, J = 7.0 Hz, 1H).

[0119] The chemical structural formula of the guest molecule G(7) is shown as follows:

[0120]

[0121] The specific preparation method and process are as follows:

[0122]

[0123] Add G(1) (500 mg, 1.15 mmol) and 20 mL of glacial acetic acid to a 100 mL round-bottom flask. After slowly dropping liquid bromine (399 mg, 2.50 mmol) into the flask, stir at room temperature for 10 hours. After the reaction is completed, slowly pour the reaction solution into 100 mL of a 5% potassium hydroxide solution, and filter to collect the filter residue. Finally, the crude product is purified by a silica gel column (eluent: dichloromethane / n-hexane, where the volume ratio of dichloromethane to n-hexane is 1:10) to obtain a pale yellow solid (237 mg, yield: 35%).

[0124] The chemical structural formula of the guest molecule G(8) is shown as follows:

[0125]

[0126] The specific preparation method and process are as follows:

[0127]

[0128] Add G(7) (1000 mg, 1.69 mmol) to a 100 mL round-bottom flask. Under a nitrogen atmosphere, add 50 mL of ultradry tetrahydrofuran to the flask. Place the flask in a liquid nitrogen-acetone bath and cool the temperature to -78 °C. Then add n-butyllithium (4.2 mL, 6.78 mmol) thereto and stir at -78 °C for 2 hours. Subsequently, add trimethyl borate (1.94 mL, 16.90 mmol) to the flask. After 1 hour, restore the reaction to room temperature. Then add HCl (3 M, 20 mL) to the flask and continue stirring for 2 hours. After the reaction is completed, extract with dichloromethane and water, and collect the organic phase. Finally, purify the crude product by silica gel column chromatography (eluent: petroleum ether / ethyl acetate, where the volume ratio of petroleum ether to ethyl acetate is 1:1) to obtain a white solid (362 mg, yield: 42%).

[0129] The chemical structural formula of the guest molecule G(9) is shown as follows

[0130]

[0131] The specific preparation method and preparation process are as follows

[0132]

[0133] Add G(1) (1000 mg, 2.30 mmol) and 20 mL of ultradry DMF to a 100 mL round-bottom flask. Under a nitrogen atmosphere and at 0 °C, slowly add phosphorus oxychloride (21.5 mL, 230 mmol) to the flask. After continuing to stir for 30 minutes, raise the temperature to 80 °C and continue the reaction for 12 hours. After the reaction is completed, cool to room temperature, pour the reaction solution into ice water, adjust the pH to 7 with sodium hydroxide solution, and then filter to obtain a filter residue. Finally, purify the filter residue by silica gel column chromatography (eluent: petroleum ether / ethyl acetate, where the volume ratio of petroleum ether to ethyl acetate is 2:1) to obtain a yellow solid G(9) (397 mg, 35.3%). 1 H NMR(400MHz,CDCl 3 ):δ9.69(s,2H),8.81(d,2H,J=8.3Hz),8.05(d,2H,J=8.0Hz),7.83(dt,2H,J 1 =7.3Hz,J 2 =3.7Hz),7.75(t,2H,J 1 =7.7Hz),7.63(t,2H,J=7.6Hz),7.52(d,4H,J=8.9Hz),7.48(dd,2H,J 1 =5.9Hz,J 2 =3.5Hz),6.98(d,4H,J=8.9Hz)。

[0134] The chemical structural formula of the guest molecule G(10) is shown as follows:

[0135]

[0136] The specific preparation method and process are as follows:

[0137]

[0138] Add G(7) (500 mg, 0.85 mmol), 4-pyridineboronic acid (522 mg, 4.25 mmol), potassium carbonate (1935 mg, 14.00 mmol), tetrakis(triphenylphosphine)palladium (98 mg, 0.085 mmol), 28 mL of tetrahydrofuran and 7 mL of water into a 100 mL two-necked flask. Under a nitrogen atmosphere, heat to 80 °C and reflux for 16 h. Subsequently, after the flask is cooled to room temperature, the mixed solution is extracted three times with dichloromethane and water to obtain a black oily substance. Finally, it is purified by silica gel column (eluent: petroleum ether / ethyl acetate, where the volume ratio of petroleum ether to ethyl acetate is 4:1) to obtain a light green solid (232 mg, yield: 46%).

[0139] The chemical structural formula of the host molecule H(1) is shown as follows:

[0140]

[0141] The chemical structural formula of the host molecule H(2) is shown as follows:

[0142]

[0143] The chemical structural formula of the host molecule H(3) is shown as follows:

[0144]

[0145] The chemical structural formula of the host molecule H(4) is shown as follows:

[0146]

[0147] The chemical structural formula of the host molecule H(5) is shown as follows:

[0148]

[0149] The chemical structural formula of the host molecule H(6) is shown as follows:

[0150]

[0151] The chemical structural formula of the host molecule H(12) is shown as follows:

[0152]

[0153] The chemical structural formula of the host molecule H(18) is shown as follows

[0154]

[0155] Example 1

[0156] The guest molecule dihydrodibenzophenazine derivative G(1) was mixed with the host molecule H(1) (the molar ratio of the guest molecule G(1) to the host molecule H(1) was 0.2:100) in a Schlenk tube. After heating at 50 °C to completely melt the mixture of the host molecule H(1) and the guest molecule G(1), it was slowly cooled to room temperature to obtain the organic room temperature phosphorescent material G(1)+H(1) based on the phenazine derivative G(1).

[0157] The afterglow schematic diagram of the organic room temperature phosphorescent material G(1)+H(1) prepared in this example is as Figure 1 shown;

[0158] Figure 2 are the solid-state fluorescence spectrum, phosphorescence spectrum, photoluminescence spectrum and phosphorescence lifetime spectrum of the organic room temperature phosphorescent doped material prepared using G(1)+H(1) at room temperature. The fluorescence emission of this doped material is at 419 nm, 447 nm, 481 nm, emitting blue fluorescence; the phosphorescence emission is at 570 nm, emitting orange phosphorescence; the phosphorescence lifetime at 570 nm is 330 ms; the phosphorescence quantum yield is 8.7%; after placing the material in air for 6 months, it still has excellent room temperature phosphorescent properties and still shows orange phosphorescence at room temperature.

[0159] Example 2

[0160] The guest molecule dihydrodibenzophenazine derivative G(3) was mixed with the host molecule H(1) (the molar ratio of the guest molecule G(3) to the host molecule H(1) was 0.2:100) in a Schlenk tube. After heating at 50 °C to completely melt the mixture of the host molecule H(1) and the guest molecule G(3), it was slowly cooled to room temperature to obtain the organic room temperature phosphorescent material G(3)+H(1) based on the phenazine derivative G(3).

[0161] Figure 3Solid fluorescence spectrum, phosphorescence spectrum, photoluminescence spectrum and phosphorescence lifetime spectrum at room temperature of the organic room-temperature phosphorescent doped material prepared using G(3)+H(1). The fluorescence emission of this doped material is at 419 nm, 447 nm, and 481 nm, emitting blue fluorescence; the phosphorescence emission is at 570 nm, emitting orange phosphorescence; the phosphorescence lifetime at 570 nm is 261 ms; the phosphorescence quantum yield is 5.1%; after the material is placed in air for 6 months, it still has excellent room-temperature phosphorescent properties and still shows orange phosphorescence at room temperature.

[0162] Example 3

[0163] The guest molecule dihydrodibenzophenazine derivative G(1) and the host molecule H(3) were mixed (the molar ratio of the guest molecule G(1) to the host molecule H(3) is 0.2:100) in a Schlenk tube. After heating at 130 °C to completely melt the mixture of the host molecule H(3) and the guest molecule G(1), it was slowly cooled to room temperature to obtain the organic room-temperature phosphorescent material G(1)+H(3) based on the phenazine derivative G(1).

[0164] The afterglow schematic diagram of the organic room-temperature phosphorescent material G(1)+H(3) based on the phenazine derivative G(1) prepared in this example is as Figure 1 shown;

[0165] Figure 4 Solid fluorescence spectrum, phosphorescence spectrum, photoluminescence spectrum and phosphorescence lifetime spectrum at room temperature of the organic room-temperature phosphorescent doped material prepared using G(1)+H(3). The fluorescence emission of this doped material is at 421 nm, emitting blue fluorescence; the phosphorescence emission is at 530 nm, emitting yellow phosphorescence; the phosphorescence lifetime at 530 nm is 125 ms; the phosphorescence quantum yield is 4.8%; after the material is placed in air for 6 months, it still has excellent room-temperature phosphorescent properties and still shows yellow phosphorescence at room temperature.

[0166] Example 4

[0167] The guest molecule dihydrodibenzophenazine derivative G(3) and the host molecule H(3) were mixed (the molar ratio of the guest molecule G(3) to the host molecule H(3) is 0.2:100) in a Schlenk tube. After heating at 130 °C to completely melt the mixture of the host molecule H(3) and the guest molecule G(3), it was slowly cooled to room temperature to obtain the organic room-temperature phosphorescent material G(3)+H(3) based on the phenazine derivative G(3).

[0168] Figure 5Solid fluorescence spectrum, phosphorescence spectrum, photoluminescence spectrum and phosphorescence lifetime spectrum at room temperature of the organic room temperature phosphorescent doped material prepared using G(3)+H(3). The fluorescence emission of this doped material is at 440 nm, emitting blue fluorescence; the phosphorescence emission is at 530 nm, emitting yellow phosphorescence; the phosphorescence lifetime at 530 nm is 151 ms respectively, and the phosphorescence quantum yield is 7.0%; after the material is placed in air for 6 months, it still has excellent room temperature phosphorescent properties and still shows yellow phosphorescence at room temperature.

[0169] Example 5

[0170] The guest molecule dihydrodibenzophenazine derivative G(1) and the host molecule H(4) were mixed (the molar ratio of the guest molecule G(1) to the host molecule H(4) is 0.2:100) in a Schlenk tube. After heating at 85 °C to completely melt the mixture of the host molecule H(4) and the guest molecule G(1), it was slowly cooled to room temperature to obtain the organic room temperature phosphorescent material G(1)+H(4) based on the phenazine derivative G(1).

[0171] The afterglow schematic diagram of the organic room temperature phosphorescent material G(1)+H(4) based on the phenazine derivative G(1) prepared in this example is as Figure 1 shown;

[0172] Figure 6 Solid fluorescence spectrum, phosphorescence spectrum, photoluminescence spectrum and phosphorescence lifetime spectrum at room temperature of the organic room temperature phosphorescent doped material prepared using G(1)+H(4). The fluorescence emission of this doped material is at 448 nm, emitting blue fluorescence; the phosphorescence emission is at 550 nm, emitting yellow phosphorescence; the phosphorescence lifetime at 550 nm is 375 ms respectively; the phosphorescence quantum yield is 7.3%; after the material is placed in air for 6 months, it still has excellent room temperature phosphorescent properties and still shows yellow phosphorescence at room temperature.

[0173] Example 6

[0174] The guest molecule dihydrodibenzophenazine derivative G(3) and the host molecule H(4) were mixed (the molar ratio of the guest molecule G(3) to the host molecule H(4) is 0.2:100) in a Schlenk tube. After heating at 85 °C to completely melt the mixture of the host molecule H(4) and the guest molecule G(3), it was slowly cooled to room temperature to obtain the organic room temperature phosphorescent material G(3)+H(4) based on the phenazine derivative G(3).

[0175] Figure 7Solid fluorescence spectrum, phosphorescence spectrum, photoluminescence spectrum and phosphorescence lifetime spectrum at room temperature of the organic room-temperature phosphorescent doped material prepared using G(3)+H(4). The fluorescence emission of this doped material is at 430 nm, emitting blue fluorescence; the phosphorescence emission is at 550 nm, emitting yellow phosphorescence; the phosphorescence lifetime at 550 nm is 322 ms; the phosphorescence quantum yield is 13.3%; after the material is placed in air for 6 months, it still has excellent room-temperature phosphorescent properties and still shows yellow phosphorescence at room temperature.

[0176] Example 7

[0177] The guest molecule dihydrodibenzophenazine derivative G(1) and the host molecule H(5) were mixed (the molar ratio of the guest molecule G(1) to the host molecule H(5) was 0.2:100) in a Schlenk tube. After heating at 65 °C to completely melt the mixture of the host molecule H(5) and the guest molecule G(1), it was slowly cooled to room temperature to obtain the organic room-temperature phosphorescent material G(1)+H(5) based on the phenazine derivative G(1).

[0178] The afterglow schematic diagram of the organic room-temperature phosphorescent material G(1)+H(5) based on the phenazine derivative G(1) prepared in this example is as Figure 1 shown;

[0179] Figure 8 Solid fluorescence spectrum, phosphorescence spectrum, photoluminescence spectrum and phosphorescence lifetime spectrum at room temperature of the organic room-temperature phosphorescent doped material prepared using G(1)+H(5). The fluorescence emission of this doped material is at 437 nm, emitting blue fluorescence; the phosphorescence emission is at 550 nm, emitting yellow phosphorescence; the phosphorescence lifetime at 550 nm is 205 ms; the phosphorescence quantum yield is 5.3%; after the material is placed in air for 6 months, it still has excellent room-temperature phosphorescent properties and still shows yellow phosphorescence at room temperature.

[0180] Example 8

[0181] The guest molecule dihydrodibenzophenazine derivative G(3) and the host molecule H(5) were mixed (the molar ratio of the guest molecule G(3) to the host molecule H(5) was 0.2:100) in a Schlenk tube. After heating at 65 °C to completely melt the mixture of the host molecule H(5) and the guest molecule G(3), it was slowly cooled to room temperature to obtain the organic room-temperature phosphorescent material G(3)+H(5) based on the phenazine derivative G(3).

[0182] Figure 9Solid fluorescence spectrum, phosphorescence spectrum, photoluminescence spectrum and phosphorescence lifetime spectrum of the organic room temperature phosphorescent doped material prepared using G(3)+H(5) at room temperature. The fluorescence emission of this doped material is at 451 nm, emitting blue fluorescence; the phosphorescence emission is at 550 nm, emitting yellow phosphorescence; the phosphorescence lifetime at 550 nm is 209 ms; the phosphorescence quantum yield is 6.3%; after placing the material in air for 6 months, it still has excellent room temperature phosphorescent properties and still shows yellow phosphorescence at room temperature.

[0183] Example 9

[0184] Mix the guest molecule dihydrodibenzophenazine derivative G(2) (8.7 mg, 0.017 mmol) with the host molecule H(12) (100 mg, 0.34 mmol) (the molar ratio of the guest molecule G(2) to the host molecule H(12) is 5:100) in a flask, add 5 mL of dichloromethane solvent, dissolve completely to obtain a mixed solution; gradually add 50 mL of n-hexane dropwise to the mixed solution, stir evenly, evaporate the solvent at room temperature, filter the residue after crystallization to obtain the organic room temperature phosphorescent material G(2)+H(12) based on the phenazine derivative G(2).

[0185] Example 10

[0186] Mix the guest molecule dihydrodibenzophenazine derivative G(4) (7.8 mg, 0.017 mmol) with the host molecule H(12) (100 mg, 0.34 mmol) (the molar ratio of the guest molecule G(4) to the host molecule H(12) is 5:100) in a flask, add 5 mL of dichloromethane solvent, dissolve completely to obtain a mixed solution; gradually add 50 mL of n-hexane dropwise to the mixed solution, stir evenly, evaporate the solvent at room temperature, filter the residue after crystallization to obtain the organic room temperature phosphorescent material G(4)+H(12) based on the phenazine derivative G(4).

[0187] Example 11

[0188] Mix the guest molecule dihydrodibenzophenazine derivative G(5) (28.0 mg, 0.054 mmol) with the host molecule H(18) (100 mg, 0.27 mmol) (the molar ratio of the guest molecule G(5) to the host molecule H(18) is 20:100) in a flask, add 5 mL of dichloromethane solvent, dissolve completely to obtain a mixed solution; gradually add 50 mL of n-hexane dropwise to the mixed solution, stir evenly, evaporate the solvent at room temperature, filter the residue after crystallization to obtain the organic room temperature phosphorescent material G(5)+H(18) based on the phenazine derivative G(5).

[0189] Example 12

[0190] The guest molecule, dihydrodibenzophenazine derivative G(6) (29 mg, 0.054 mmol), was mixed with the host molecule H(18) (100 mg, 0.27 mmol) (the molar ratio of the guest molecule G(6) to the host molecule H(18) was 20:100) in a flask. 5 mL of dichloromethane solvent was added and dissolved completely to obtain a mixed solution. 50 mL of n-hexane was added dropwise to the mixed solution, stirred evenly, and the solvent was evaporated at room temperature. After crystallization, the residue was filtered to obtain the organic room temperature phosphorescent material G(6)+H(18) based on the phenazine derivative G(6).

[0191] Example 13

[0192] The guest molecule, dihydrodibenzophenazine derivative G(7) (0.14 mg, 0.00023 mmol), was mixed with the host molecule H(2) (5000 mg, 22.93 mmol) (the molar ratio of the guest molecule G(7) to the host molecule H(2) was 0.001:100) in a flask. 10 mL of dichloromethane solvent was added and dissolved completely to obtain a mixed solution. 100 mL of n-hexane was added dropwise to the mixed solution, stirred evenly, and the solvent was evaporated at room temperature. After crystallization, the residue was filtered to obtain the organic room temperature phosphorescent material G(7)+H(2) based on the phenazine derivative G(7).

[0193] Example 14

[0194] The guest molecule, dihydrodibenzophenazine derivative G(8) (0.12 mg, 0.00023 mmol), was mixed with the host molecule H(2) (5000 mg, 22.93 mmol) (the molar ratio of the guest molecule G(8) to the host molecule H(2) was 0.001:100) in a flask. 10 mL of dichloromethane solvent was added and dissolved completely to obtain a mixed solution. 100 mL of n-hexane was added dropwise to the mixed solution, stirred evenly, and the solvent was evaporated at room temperature. After crystallization, the residue was filtered to obtain the organic room temperature phosphorescent material G(8)+H(2) based on the phenazine derivative G(8).

[0195] Example 15

[0196] The guest molecule, dihydrodibenzophenazine derivative G(9) (0.38 mg, 0.00077 mmol), was mixed with the host molecule H(6) (1000 mg, 3.85 mmol) (the molar ratio of the guest molecule G(9) to the host molecule H(6) was 0.02:100) in a flask. 10 mL of dichloromethane solvent was added and dissolved completely to obtain a mixed solution. The mixed solution was spin-coated on a clean and dry quartz wafer at 600 revolutions per minute and annealed at 65 °C for 2 h to obtain the organic room temperature phosphorescent material G(9)+H(6) based on the phenazine derivative G(9).

[0197] Example 16

[0198] The guest molecule dibenzophenazine derivative G(10) (0.45 mg, 0.00077 mmol) was mixed with the host molecule H(6) (1000 mg, 3.85 mmol) (the molar ratio of the guest molecule G(10) to the host molecule H(6) was 0.02:100) in a flask, and 10 mL of dichloromethane solvent was added and completely dissolved to obtain a mixed solution. The mixed solution was spin-coated on a clean and dry quartz plate at 600 revolutions per minute and annealed at 65 °C for 2 h to obtain the organic room temperature phosphorescent material G(10)+H(6) based on the phenazine derivative G(10).

[0199] The above description of the embodiments is for the convenience of those of ordinary skill in the art to understand and use the invention. It is obvious that those skilled in the art can easily make various modifications to these embodiments and apply the general principles described herein to other embodiments without creative efforts. Therefore, the present invention is not limited to the above embodiments, and the improvements and modifications made by those skilled in the art without departing from the scope of the present invention according to the disclosure of the present invention should be within the protection scope of the present invention.

Claims

1. An organic room-temperature phosphorescent material based on phenazine derivatives, characterized in that, it is obtained by doping a guest molecule G and a host molecule H; the guest molecule G is selected from one of G1, G2, G3 or G4; the host molecule H is selected from one or more of H1, H2, H3, H4 or H5; ； ； Among them, R is selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a boronic acid group, a boronic ester group, an aldehyde group, a hydroxyl group, a pyridyl group, vinylpyridine, a carboxyl group, an alkoxy group, an acyl group, an ester group, a cyano group or a trifluoromethyl group; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 are each independently selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group, an alkoxy group or an acyl group; the number of carbon atoms of the alkyl group, alkoxy group or acyl group is 1-6; wherein, the molar ratio of the guest molecule G to the host molecule H is 0.001 - 20:100; this organic room-temperature phosphorescent material produces sky-blue fluorescence under ultraviolet light irradiation, and yellow to orange phosphorescence after turning off the ultraviolet light, with a phosphorescence quantum yield reaching 4.8 - 13.3% and a phosphorescence lifetime up to 145 - 375 ms; after placing this organic room-temperature phosphorescent material in air for 6 months, it still shows yellow or orange phosphorescence at room temperature.

2. An organic room-temperature phosphorescent material based on phenazine derivatives according to claim 1, characterized in that, the guest molecule G is selected from one of the following structural formulas: ； the host molecule H is selected from one or more of the following structural formulas; 。 3. A preparation method of an organic room-temperature phosphorescent material based on phenazine derivatives as claimed in any one of claims 1–2, characterized in that, it includes the following steps: Mix the guest molecule G and the host molecule H evenly to obtain an organic room-temperature phosphorescent material based on phenazine derivatives; the guest molecule G is selected from one of G1, G2, G3 or G4; the host molecule H is selected from one or more of H1, H2, H3, H4 or H5; ； ； Among them, R is selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a boronic acid group, a boronic acid ester group, an aldehyde group, a hydroxyl group, a pyridyl group, vinylpyridine, a carboxyl group, an alkoxy group, an acyl group, an ester group, a cyano group or a trifluoromethyl group; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 are each independently selected from one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group, an alkoxy group or an acyl group; the number of carbon atoms of the alkyl group, alkoxy group or acyl group is 1-6.

4. A preparation method of an organic room-temperature phosphorescent material based on phenazine derivatives according to claim 3, characterized in that, during the mixing process, the mixing method is selected from one or more of the heating melting method, the solvent evaporation crystallization method, the vapor diffusion eutectic method or the spin coating method.

5. A preparation method of an organic room-temperature phosphorescent material based on phenazine derivatives according to claim 4, characterized in that, the specific steps of the heating melting method are as follows: Pre-mix the guest molecule G and the host molecule H to obtain a pre-mixture, heat the pre-mixture until it is completely melted and then cool it to room temperature to obtain an organic room-temperature phosphorescent material based on phenazine derivatives.

6. A preparation method of an organic room-temperature phosphorescent material based on phenazine derivatives according to claim 4, characterized in that, the specific steps of the solvent evaporation crystallization method are as follows: Pre-mix the guest molecule G and the host molecule H and then add a good solvent, and after complete dissolution, obtain a mixed solution; mix the mixed solution with a poor solvent, evaporate the solvent, crystallize and then perform post-treatment to obtain an organic room-temperature phosphorescent material based on phenazine derivatives.

7. A preparation method of an organic room-temperature phosphorescent material based on phenazine derivatives according to claim 4, characterized in that, the specific steps of the vapor diffusion eutectic method are as follows: Pre-mix the guest molecule G and the host molecule H and then add a good solvent, and after complete dissolution, obtain a mixed solution; mix the mixed solution with a poor solvent, seal it and place it in a cool and dry place until crystals grow, then an organic room-temperature phosphorescent material based on phenazine derivatives is obtained.

8. A preparation method of an organic room-temperature phosphorescent material based on phenazine derivatives according to claim 4, characterized in that, the specific steps of the spin coating method are as follows: The guest molecule G and the host molecule H are pre-mixed and then added to a good solvent. After complete dissolution, a mixed solution is obtained. The mixed solution is spin-coated on a substrate, and after-treatment is carried out to obtain an organic room-temperature phosphorescent material based on a phenazine derivative.

9. Application of an organic room-temperature phosphorescent material based on a phenazine derivative as described in any one of claims 1 to 2 in anti-counterfeiting, information encryption, and bioimaging.

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