A super long room temperature phosphorescent material and its preparation method and application

Abstract

The present invention provides an ultra-long room temperature phosphorescent material and a preparation method and application thereof, wherein the ultra-long room temperature phosphorescent material comprises a main component and a guest component doped in the main component, wherein the main component comprises triphenylphosphine, and the guest component comprises an indolopyrrole derivative. The present invention prepares an ultra-long room temperature phosphorescent material by doping an indolopyrrole derivative in triphenylphosphine, and the material has the advantages of long phosphorescence life and high efficiency, and has good application prospects in the fields of anti-counterfeiting, encryption, functional ink, etc.

Description

Technical Field

[0001] The present invention belongs to the field of material technology, and in particular relates to an ultra-long room temperature phosphorescent material and a preparation method and application thereof. Background Art

[0002] Room temperature long afterglow materials usually have a long lifetime (>100ms), which can eliminate the interference of excitation light sources and fluorescent background. Therefore, they have important potential applications in data storage and encryption anti-counterfeiting, optoelectronic devices, optical recording, molecular switches, biological imaging, etc. Compared with inorganic luminescent materials, organic luminescent materials have the advantages of simple synthesis, rich variety, low toxicity, and easy processing. Therefore, in recent years, the design of organic long afterglow materials has aroused the interest of researchers.

[0003] However, according to the El-Sayed rule, the intersystem crossing process (excitons from 1 (nπ*) singlet transition to 3 (nπ*) triplet or from 1 (ππ*) single state transition to 3 (ππ*) triplet state) is theoretically spin-forbidden. In addition, the triplet excitons of organic molecules are easily quenched and inactivated by oxygen in the air. Therefore, it is relatively difficult to achieve organic room temperature phosphorescence emission in pure organic molecules, especially ultra-long room temperature phosphorescence. In recent years, great progress has been made in the research on pure organic room temperature phosphorescent materials, and many effective material design and preparation strategies have been developed successively. These strategies mainly include: 1. Providing a rigid environment for organic molecules through crystal engineering and forming special molecular aggregates; 2. Introducing heteroatoms and heavy halogen atoms into molecules to improve their intersystem crossing efficiency; 3. Polymerizing organic molecules into polymers; 4. Using host-guest doping to incorporate organic molecules into solid matrices that can isolate oxygen and restrict molecular motion, etc. Among them, host-guest doping materials have received more attention due to their advantages such as simple preparation, excellent performance, and convenient modification. In the host-guest doping system, the guest molecule acts as an emitter, and the host's crystal matrix can restrict the intramolecular motion of the guest molecule, effectively preventing the triplet state of the guest molecule from oxygen quenching. In addition, some research results show that the host material can promote the transfer process of guest excitons between different energy levels. However, at present, such materials generally have a short lifetime or low phosphorescence quantum yield, which greatly limits the application of room temperature phosphorescent materials. Based on this, the development of luminescent materials with long lifetime and high efficiency has important theoretical and practical significance. Summary of the invention

[0004] The present invention aims to solve at least one of the technical problems existing in the above-mentioned prior art. To this end, the first aspect of the present invention provides an ultra-long room temperature phosphorescent material, which has the advantages of long phosphorescence lifetime and high quantum yield.

[0005] The second aspect of the present invention provides a method for preparing the ultra-long room temperature phosphorescent material.

[0006] The third aspect of the present invention provides an anti-counterfeiting material comprising the ultra-long room temperature phosphorescent material.

[0007] The fourth aspect of the present invention proposes an anti-counterfeiting method using the ultra-long room temperature phosphorescent material.

[0008] The fifth aspect of the present invention proposes an application of the ultra-long room temperature phosphorescent material in anti-counterfeiting materials.

[0009] According to a first aspect of the present invention, an ultra-long room temperature phosphorescent material is provided, comprising a host component and a guest component doped in the host component, wherein the host component comprises triphenylphosphine, and the guest component comprises an indolopyrrole derivative.

[0010] In some embodiments of the present invention, the indolopyrrole derivative has a structural formula shown in Formula I:

[0011] Wherein, R1, R2, and R3 are independently selected from H, D, halogen or ester group.

[0012] In some preferred embodiments of the present invention, the indolopyrrole derivative has a structural formula shown in Formula II:

[0013] Wherein, R1, R2, and R3 are as defined above.

[0014] In some more preferred embodiments of the present invention, the indolopyrrole derivative is selected from the following compounds:

[0015] Depending on the type of doped indole pyrrole derivatives, the phosphorescence efficiency, lifespan and other properties of the ultra-long room temperature phosphorescent material can be regulated.

[0016] In some more preferred embodiments of the present invention, the doping includes physical doping.

[0017] In some more preferred embodiments of the present invention, the mass ratio of the host component to the guest component is (10 7 ~10 2 ): 5; Preferably, the mass ratio of the main component to the guest component is (10 5 ~10 3 ):5.

[0018] In some more preferred embodiments of the present invention, the mass ratio of the triphenylphosphine to the indolopyrrole derivative is (105 ~10 3 ): 5. According to the concentration of the doped indole pyrrole derivative, the phosphorescence efficiency, life span and other properties of the ultra-long room temperature phosphorescent material can be regulated.

[0019] According to a second aspect of the present invention, a method for preparing an ultra-long room temperature phosphorescent material is provided, comprising the following steps:

[0020] The indole pyrrole derivative solid powder is added into triphenylphosphine crystals, heated to melt, and stirred to obtain the ultra-long room temperature phosphorescent material.

[0021] In some embodiments of the present invention, the heating and melting temperature is 75°C to 150°C, preferably 80°C to 100°C.

[0022] In some preferred embodiments of the present invention, the stirring time is 1 min to 30 min, preferably 5 min to 10 min.

[0023] According to a third aspect of the present invention, an anti-counterfeiting material is provided, comprising the ultra-long room temperature phosphorescent material.

[0024] According to a fourth aspect of the present invention, an anti-counterfeiting method is proposed, comprising the following steps: preparing the ultra-long room temperature phosphorescent material into an anti-counterfeiting pattern.

[0025] In some embodiments of the present invention, the anti-counterfeiting method comprises the following steps: dissolving the ultra-long room temperature phosphorescent material in an organic solvent, and then using the obtained solution as ink to apply an anti-counterfeiting pattern.

[0026] In some preferred embodiments of the present invention, the organic solvent is at least one of ethyl acetate, propyl acetate, butyl acetate, ethanol, dichloromethane, acetone, tetrahydrofuran, acetonitrile and toluene.

[0027] In some more preferred embodiments of the present invention, the anti-counterfeiting method further comprises the step of irradiating the anti-counterfeiting pattern with an excitation light source for anti-counterfeiting identification. By utilizing the difference in afterglow performance of the triphenylphosphine-based long afterglow material contained in different parts of the anti-counterfeiting pattern, the change of the afterglow pattern over time after the excitation light source is removed is observed, thereby achieving the anti-counterfeiting function.

[0028] In some more preferred embodiments of the present invention, the excitation light source is ultraviolet light.

[0029] According to a fifth aspect of the present invention, a use of the ultra-long room temperature phosphorescent material in an anti-counterfeiting material is proposed.

[0030] The beneficial effects of the present invention are:

[0031] 1. The ultra-long room temperature phosphorescent material of the present invention is prepared by doping indole pyrrole derivatives into triphenylphosphine to obtain a triphenylphosphine-based ultra-long room temperature phosphorescent material, which has the advantages of long phosphorescence life and high efficiency, and has good application prospects in the fields of anti-counterfeiting, encryption, functional inks, etc.

[0032] 2. In the present invention, materials with different mass ratios of main component and guest component are selected according to actual needs, and are prepared into specific anti-counterfeiting patterns. The two materials have similar steady-state luminescence but different ultra-long room temperature phosphorescence lifetimes, so that the color and shape of the anti-counterfeiting pattern change after the excitation light source is removed, thereby achieving the anti-counterfeiting function.

[0033] 3. The present invention utilizes the difference in afterglow performance of the triphenylphosphine-based long afterglow material contained in different parts of the anti-counterfeiting pattern to observe the change of the afterglow pattern over time after the excitation light source is removed, thereby achieving the anti-counterfeiting function. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] The present invention will be further described below with reference to the accompanying drawings and embodiments, wherein:

[0035] Figure 1 This is a diagram showing the anti-counterfeiting effect of the material in Example 5 of the present invention under ultraviolet light excitation.

[0036] Figure 2 The photographs are of the main material triphenylphosphine and the guest material indole pyrrole derivatives (1) to (3) of the present invention when irradiated with a 365nm ultraviolet lamp and after it is turned off.

[0037] Figure 3 These are luminescent photos of the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 of the present invention when irradiated with a 365nm ultraviolet lamp and after it is turned off.

[0038] Figure 4 This is a normalized steady-state luminescence spectrum diagram of the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 of the present invention.

[0039] Figure 5 This is a normalized delayed emission spectrum diagram of the ultra-long room temperature phosphorescent material prepared in Examples 1 to 4 of the present invention.

[0040] Figure 6 The phosphorescence decay curves of the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 of the present invention.

[0041] Figure 7 This is a graph of the phosphorescence quantum yield of the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 of the present invention. DETAILED DESCRIPTION

[0042] The following will be combined with the embodiments to clearly and completely describe the concept of the present invention and the technical effects produced, so as to fully understand the purpose, characteristics and effects of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, other embodiments obtained by those skilled in the art without creative work are all within the scope of protection of the present invention.

[0043] Example 1

[0044] This embodiment prepares an ultra-long room temperature phosphorescent material, and the specific process is as follows:

[0045] First, prepare the compound of formula (1), the specific process is as follows:

[0046]

[0047] (1) Phenylpyrrole (2.01 g, 14.00 mmol), 1-bromo-2-nitrobenzene (11.25 g, 56.00 mmol), Cs2CO3 (36.70 g, 110.00 mmol) and 60 mL of acetonitrile solvent were added to a 500 mL three-necked flask under argon atmosphere. The mixture was heated to 80°C and stirred for 48 hours before cooling to room temperature. The solid was filtered and the filtrate was retained. The solvent was removed from the filtrate by rotary evaporation. The crude product was separated by column chromatography using a mixed solution of dichloromethane and petroleum ether (7:10, V / V) as the mobile phase and 200-300 mesh silica gel powder. The product was dried in vacuo to obtain a yellow solid of 2,5-di(2-nitrophenyl)-1-phenyl-1H-pyrrole with a mass of 2.80 g and a yield of 52%.

[0048] (2) Under argon atmosphere, 2,5-di(2-nitrophenyl)-1-phenyl-1H-pyrrole (2.40 g, 6.23 mmol) obtained in step (1) and 25 mL of triethyl phosphite were added to a 250 mL three-necked flask. The mixture was heated to 150°C and refluxed for 24 hours, then cooled to room temperature. The triethyl phosphite solvent was then removed by rotary evaporator, and the obtained crude product was separated by column chromatography using a mixed solution of ethyl acetate and petroleum ether (1:4, V / V) as the mobile phase and 200-300 mesh silica gel powder. The obtained product was then reprecipitated using dichloromethane as the good solvent and petroleum ether as the poor solvent, and vacuum dried to obtain compound A (chemical name: 11-phenyl-6,11-dihydro-5H-pyrrolo[3,2-b:4,5-b']diindole), a yellow solid powder with a mass of 1.10 g and a yield of 55%.

[0049] (3) Under argon atmosphere, compound A (0.15 g, 0.47 mmol), bromobenzene (1.46 g, 9.35 mmol), Ruphos (80 mg) and K3PO4 (1.00 g, 4.67 mmol) were added to a 250 mL three-necked flask, followed by the addition of 30 mL of toluene solvent, and the reaction was allowed to bubbling for 40 minutes. Pd2(dba3) catalyst was added, and the temperature was raised to 120°C and refluxed for 24 hours, followed by cooling to room temperature. The toluene solvent was then removed by rotary evaporator, and the obtained crude product was separated by column chromatography using a mixed solution of dichloromethane and petroleum ether (1:1, V / V) as the mobile phase and 200-300 mesh silica gel powder. The obtained product was then reprecipitated using dichloromethane as the good solvent and methanol as the poor solvent, and after vacuum drying, a light yellow solid powder of formula (1) was obtained, with a mass of 0.18 g and a yield of 82%.

[0050] The ultra-long room temperature phosphorescent material is prepared by using the compound of formula (1), and the specific process is as follows:

[0051] 0.05 mg of the compound of formula (1) and 100 mg of triphenylphosphine were placed in a 1.5 mL glass sample bottle, heated to a molten state at 95° C., stirred for 10 min, and then cooled to room temperature to obtain an ultra-long room temperature phosphorescent material with a mass fraction of 0.05% of the compound of formula (1).

[0052] Example 2

[0053] This embodiment prepares an ultra-long room temperature phosphorescent material, and the specific process is as follows:

[0054] First, prepare the compound of formula (2), the specific process is as follows:

[0055]

[0056] (1) Under argon atmosphere, compound A (0.10 g, 0.31 mmol) prepared in step (2) of Example 1, ethyl 4-bromobenzoate (0.18 g, 0.78 mmol), Ruphos 80 mg, K3PO4 (0.20 g, 0.93 mmol) and 15 mL of toluene were added to a 250 mL three-necked flask. After bubbling argon for 40 minutes, Pd2(dba3) catalyst was added, the temperature was raised to 120°C and refluxed for 24 hours, and then cooled to room temperature. The toluene solvent was then removed by rotary evaporator, and the obtained crude product was separated by column chromatography using a mixed solution of dichloromethane and petroleum ether (1:1, V / V) as the mobile phase and 200-300 mesh silica gel powder. The obtained product was then reprecipitated using dichloromethane as the good solvent and methanol as the poor solvent. After vacuum drying, a yellow-green solid powder of intermediate 1 was obtained, with a mass of 0.06 g and a yield of 41%.

[0057] (2) Under argon atmosphere, intermediate 1 (0.16 g, 0.34 mmol), bromobenzene (0.13 g, 0.85 mmol), Ruphos 80 mg, K3PO4 (0.22 g, 1.02 mmol) and 30 mL toluene solvent were added to a 250 mL three-necked flask. After bubbling argon for 40 minutes, Pd2(dba3) catalyst was added, the temperature was raised to 120°C and refluxed for 24 hours, and then cooled to room temperature. The toluene solvent was then removed by rotary evaporator, and the obtained crude product was separated by column chromatography using a mixed solution of dichloromethane and petroleum ether (1:1, V / V) as the mobile phase and 200-300 mesh silica gel powder. The obtained product was then reprecipitated using dichloromethane as the good solvent and methanol as the poor solvent. After vacuum drying, a light yellow solid powder of the compound of formula (2) was obtained, with a mass of 0.17 g and a yield of 92%.

[0058] The ultra-long room temperature phosphorescent material is prepared by using the compound of formula (2), and the specific process is as follows:

[0059] 0.05 mg of the compound of formula (2) and 100 mg of triphenylphosphine were placed in a 1.5 mL glass sample bottle, heated to a molten state at 95° C., stirred for 10 min, and then cooled to room temperature to obtain an ultra-long room temperature phosphorescent material with a mass fraction of 0.05% of the compound of formula (2).

[0060] Example 3

[0061] This embodiment prepares an ultra-long room temperature phosphorescent material, and the specific process is as follows:

[0062] First, prepare the compound of formula (3), the specific process is as follows:

[0063]

[0064] Under argon atmosphere, compound A (0.20 g, 0.62 mmol), ethyl 4-bromobenzoate (0.86 g, 3.74 mmol), Ruphos 80 mg, K3PO4 (0.66 g, 3.10 mmol) and 30 mL of toluene were added to a 250 mL three-necked flask. Argon was bubbled for 40 minutes, Pd2 (dba3) catalyst was added, the temperature was raised to 120°C and refluxed for 24 hours, and then cooled to room temperature. The toluene solvent was then removed by rotary evaporator, and the crude product was separated by column chromatography using a mixed solution of dichloromethane and petroleum ether (1:1, V / V) as the mobile phase and 200-300 mesh silica gel powder. The product was reprecipitated using dichloromethane as the good solvent and methanol as the poor solvent. After vacuum drying, an off-white solid powder of the compound of formula (2) was obtained, with a mass of 0.30 g and a yield of 78%.

[0065] The ultra-long room temperature phosphorescent material is prepared by using the compound of formula (3), and the specific process is as follows:

[0066] 0.05 mg of the compound of formula (3) and 100 mg of triphenylphosphine were placed in a 1.5 mL glass sample bottle, heated to a molten state at 95° C., stirred for 10 min, and then cooled to room temperature to obtain an ultra-long room temperature phosphorescent material with a mass fraction of 0.05% of the compound of formula (3).

[0067] Example 4

[0068] This embodiment prepares an ultra-long room temperature phosphorescent material, and the specific process is as follows:

[0069] 0.5 mg of the compound of formula (3) and 100 mg of triphenylphosphine were placed in a 1.5 mL glass sample bottle, heated to a molten state at 95° C., stirred for 10 min, and then cooled to room temperature to obtain an ultra-long room temperature phosphorescent material with a mass fraction of 0.5% of the compound of formula (3).

[0070] Example 5

[0071] This embodiment provides the use of the above materials, and the ultra-long room temperature phosphorescent materials in Embodiments 3 and 4 and the compound of formula (3) are prepared into anti-counterfeiting patterns for anti-counterfeiting. The process includes the following steps:

[0072] (1) Take 100 mg of the ultralong room temperature phosphorescent material in Example 4 and use 380 μL of ethyl acetate solvent to sonicate until it is uniformly dissolved to obtain a colorless and transparent solution 1.

[0073] (2) Take 100 mg of the ultralong room temperature phosphorescent material in Example 3 and use 380 μL of ethyl acetate solvent to sonicate until it is uniformly dissolved to obtain a colorless and transparent solution 2.

[0074] (3) Weigh 1.5 mg of the compound of formula (3), add 2.4 mL of ethyl acetate solvent, and dissolve it by ultrasonic until it is uniform, to obtain a compound of formula (3) with a concentration of 1×10 -3 mol / L transparent solution 3.

[0075] (4) The above three solutions are used as inks to form the three parts of the anti-counterfeiting pattern. By taking advantage of the different characteristics of the ultra-long room temperature phosphorescence life, the color and shape of the anti-counterfeiting pattern change after the excitation light source is removed, thereby achieving the anti-counterfeiting function. The results are as follows Figure 1 shown.

[0076] from Figure 1 It can be seen that the prepared indole pyrrole derivative-doped triphenylphosphine-based ultra-long room temperature phosphorescent material can be used for anti-counterfeiting.

[0077] Test example

[0078] This test example tests the performance of pure guest materials indole pyrrole derivatives and room temperature phosphorescent materials. The specific process is as follows:

[0079] The photos of the pure host material triphenylphosphine and the pure guest material indole pyrrole derivative compounds of formula (1) to formula (3) when irradiated with 365nm ultraviolet light and after it is turned off are shown in the figure below. Figure 2 shown.

[0080] from Figure 2 It can be seen that the pure guest material and the main material triphenylphosphine used in the present invention do not have ultra-long room temperature phosphorescence properties after being excited by a 365nm ultraviolet lamp. The guest material needs to be doped into triphenylphosphine to produce ultra-long room temperature phosphorescence properties.

[0081] The ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 are shown in the following pictures when irradiated with a 365nm ultraviolet lamp and after being turned off. Figure 3 shown.

[0082] from Figure 3 As can be seen from Table 1, when the indolopyrrole derivative compounds of formula (1) to formula (3) are doped into the main molecule, ultra-long room temperature phosphorescence properties will be produced. In room temperature air, the phosphorescence lifetime can be up to 1.75 s and the efficiency can be up to 41.05%. As the chemical structure and doping concentration of the indolopyrrole derivatives change, the steady-state luminescent color of the triphenylphosphine-based ultra-long room temperature phosphorescent material prepared in Examples 1 to 4 will change from blue to sky blue, thereby achieving the regulation of the ultra-long room temperature phosphorescence lifetime and efficiency of the ultra-long room temperature phosphorescent material.

[0083] The performance tests were conducted on the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4, mainly to examine the ultra-long room temperature phosphorescent spectrum and color, quantum yield, lifespan and other properties of the target materials. All tests were conducted on an Edinburgh FLS980 steady-state transient fluorescence spectrometer with an integrating sphere. The results are shown in Figures 4 to 7 As shown in Table 1.

[0084] Table 1 Photophysical properties of room temperature phosphorescent materials in the examples

[0085]

[0086]

[0087] a Lifetime at 515nm; b Lifetime at 518nm; c Lifetime at 521nm

[0088] Figure 4 The normalized steady-state luminescence spectra of the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 are shown in Table 1. Figure 4It can be seen that in the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4, the chemical structures and doping concentrations of the guest molecules used are different, and their steady-state luminescence spectra are quite different. This result further illustrates that the steady-state luminescence color of the ultra-long room temperature phosphorescent material can be adjusted by changing the structure and doping concentration of the guest molecules.

[0089] Figure 5 The normalized delayed luminescence spectra of the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 are shown in FIG. Figure 5 It can be seen that the emission peaks of the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 are located in the range of 515 to 555 nm, which means that they can all emit yellow-green ultra-long room temperature phosphorescence.

[0090] Figure 6 The phosphorescence attenuation curves of the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 are shown in FIG. Figure 6 It can be seen that the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 have phosphorescence lifetimes of more than 1.50 s, with the longest being 1.75 s, and the room temperature phosphorescence lifetime of the material can be regulated by changing the chemical structure of the guest molecule.

[0091] Figure 7 The phosphorescence quantum yield diagram of the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 is shown in FIG. Figure 7 It can be seen that the ultra-long room temperature phosphorescent materials prepared in Examples 1 to 4 have a relatively high phosphorescent quantum yield, which can even reach 41.05%, and the phosphorescent quantum yield of the material can be regulated by changing the chemical structure of the guest molecule.

[0092] Depend on Figure 6 and Figure 7 It can be seen that by utilizing the difference in phosphorescence lifetime and phosphorescence quantum yield, the prepared ultra-long room temperature phosphorescent materials can be applied to anti-counterfeiting, information encryption, functional inks and coatings and other fields.

[0093] In summary, in the embodiments of the present invention, with indole and carbazole derivatives as the guest and triphenylphosphine as the main body, the prepared organic material can emit phosphorescence with long life and high efficiency in room temperature air through physical doping. By changing the chemical structure and doping concentration of the indole and pyrrole derivatives, the steady-state luminescent color of the triphenylphosphine-based ultra-long room temperature phosphorescent material and the life and efficiency of its phosphorescent emission can be regulated. The unique ultra-long room temperature phosphorescent luminescent properties of the prepared material can also be used to achieve anti-counterfeiting functions. It can be seen that the prepared indole and pyrrole derivative doped triphenylphosphine-based material has the advantages of long phosphorescent life, high efficiency, and the steady-state luminescent color can be adjusted by changing the guest molecular structure and doping concentration. It can be used as an anti-counterfeiting material, and even has important potential applications in the fields of data encryption and functional inks.

[0094] The above is a detailed description of the embodiments of the present invention, but the present invention is not limited to the above embodiments. Various changes can be made within the knowledge of ordinary technicians in the relevant technical field without departing from the purpose of the present invention. In addition, the embodiments of the present invention and the features in the embodiments can be combined with each other without conflict.

Claims

1. An ultra-long room temperature phosphorescent material, characterized in that: It comprises a main component and a guest component doped in the main component, wherein the main component comprises triphenylphosphine, and the guest component comprises an indolopyrrole derivative; The indolopyrrole derivative is .

2. The ultra-long room temperature phosphorescent material according to claim 1, characterized in that: The doping includes physical doping.

3. The ultra-long room temperature phosphorescent material according to claim 1, characterized in that: The mass ratio of the main component to the guest component is (10 7 ~10 2 ):

5.

4. The ultra-long room temperature phosphorescent material according to claim 1, characterized in that: The mass ratio of the triphenylphosphine to the indolopyrrole derivative is (10 5 ~10 3 ):

5.

5. A method for preparing an ultra-long room temperature phosphorescent material, characterized in that: The following steps are involved: The solid powder of the indole pyrrole derivative is added to the triphenylphosphine crystal, heated to melt, and stirred to obtain the ultra-long room temperature phosphorescent material as claimed in any one of claims 1 to 4.

6. An anti-counterfeiting material, comprising the ultra-long room temperature phosphorescent material as described in any one of claims 1 to 4.

7. An anti-counterfeiting method, comprising the following steps: preparing an anti-counterfeiting pattern from the ultra-long room temperature phosphorescent material as described in any one of claims 1 to 4.

8. The anti-counterfeiting method according to claim 7, characterized in that: The anti-counterfeiting method further comprises the step of irradiating the anti-counterfeiting pattern with an excitation light source to perform anti-counterfeiting identification.

9. Use of the ultra-long room temperature phosphorescent material as claimed in any one of claims 1 to 4 in anti-counterfeiting materials.

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