阅读说明：本技术 基于蒽衍生物的激基缔合物发光材料及其制备方法和应用 (Excimer luminescent material based on anthracene derivative and preparation method and application thereof ) 是由 李倩倩 廖秋艳 李振 李贺华 姚鹏飞 于 2021-09-13 设计创作，主要内容包括：本发明提供了一种基于蒽衍生物的激基缔合物发光材料,所述基于蒽衍生物的激基缔合物发光材料的结构式如下式X2A所示：相比于常见的激基缔合物材料,该材料对浓度没有依赖性,在稀溶液中就能实现激基缔合物发光。本发明还提供上述基于蒽衍生物的激基缔合物发光材料的制备方法,其反应条件较温和,产率高。本发明还提供上述基于蒽衍生物的激基缔合物发光材料的应用。(The invention provides an anthracene derivative-based excimer luminescent material, which has a structural formula shown as the following formula X2A: compared with common excimer materials, the material has no dependence on concentration, and can realize excimer luminescence in dilute solution. The invention also provides a preparation method of the anthracene derivative-based excimer luminescent material, which has mild reaction conditions and high yield. The invention also provides the anthracene derivative-based excimer luminescent materialApplication is carried out.)

1. An anthracene derivative-based excimer light-emitting material, characterized in that the structural formula of the anthracene derivative-based excimer light-emitting material is as shown in the following formula X2A:

2. the anthracene derivative-based excimer light-emitting material according to claim 1, wherein the anthracene derivative-based excimer light-emitting material exhibits red-shifted excimer green emission when dissolved in an organic solvent or doped in a PMMA thin film;

preferably, the fluorescence quantum yield of the anthracene derivative-based excimer light-emitting material in a solid state is more than 99.9%;

more preferably, the anthracene derivative-based excimer light-emitting material is at a concentration of 10^-6～10^-2Dissolving mol/L in an organic solvent; the anthracene derivative-based excimer luminescent material is doped in the PMMA film by 0.5-2 wt%;

more preferably, the organic solvent is selected from one or more of tetrahydrofuran, dichloromethane, chloroform, methanol and ethanol.

3. A method for producing an anthracene derivative-based excimer light-emitting material according to claim 1 or 2, wherein the compound represented by formula X2A is produced from a compound represented by formula 2 and a compound represented by formula 3.

4. The method for producing an anthracene derivative-based excimer light-emitting material according to claim 3,

the reaction formula for preparing the compound represented by formula X2A from the compound represented by formula 2 and the compound represented by formula 3 is as follows:

the preparation of the compound represented by the formula X2A from the compound represented by the formula 2 and the compound represented by the formula 3 comprises the following steps:

under an inert atmosphere, putting a compound shown as a formula 2, a compound shown as a formula 3, potassium carbonate and dichloro-di-tert-butyl- (4-dimethylaminophenyl) phosphorus palladium (II) into a reaction vessel, adding tetrahydrofuran and water, heating and refluxing for 5-15 hours, and purifying to obtain a compound shown as a formula X2A;

preferably, the molar ratio of the compound shown in the formula 2 to the compound shown in the formula 3 is 1 (2-5); more preferably, the molar ratio of the potassium carbonate to the compound shown in the formula 2 is (2-6): 1; more preferably, the molar ratio of the dichloro-di-tert-butyl- (4-dimethylaminophenyl) palladium (II) phosphate to the compound shown in the formula 2 is (2-8): 100;

optionally, the purification comprises the steps of: cooling the reaction liquid to 15-35 ℃, adding a saturated sodium chloride aqueous solution into the reaction liquid, extracting with dichloromethane to obtain an organic phase, drying the organic phase with anhydrous sodium sulfate, removing the solvent, separating by silica gel column chromatography with a mixed solvent of petroleum ether and dichloromethane as an eluent, and drying;

preferably, the volume ratio of the petroleum ether to the dichloromethane in the mixed solvent is (4-6): 1.

5. The method for producing an anthracene derivative-based excimer light-emitting material according to claim 4,

the compound shown in the formula 2 is prepared from a compound shown in a formula 1;

the reaction formula for preparing the compound of formula 2 from the compound of formula 1 is as follows:

the preparation of the compound of formula 2 from the compound of formula 1 comprises the following steps:

dissolving the compound shown in the formula 1 in trichloromethane under ice bath, slowly dropwise adding a liquid bromine solution diluted by the trichloromethane, stirring at 15-35 ℃ for reaction for 10-15 hours, and purifying to obtain the compound shown in the formula 2;

preferably, the molar ratio of the compound shown in the formula 1 to liquid bromine is 1 (2-4);

optionally, the purification comprises the steps of: adding sodium sulfite aqueous solution into the reaction solution to quench reaction, extracting with dichloromethane to obtain an organic phase, drying the organic phase with anhydrous sodium sulfate, removing the solvent, separating by silica gel column chromatography with petroleum ether as eluent, and drying.

6. The method for producing an anthracene derivative-based excimer light-emitting material according to claim 5,

the synthetic route of the compound represented by the formula 1 is shown as follows:

the compound shown in the formula 1 is prepared by the following method: dissolving 9, 9-dimethylxanthene and ferric chloride in dichloromethane in ice bath, adding a tert-butyl chloride solution diluted by dichloromethane, stirring for 10-15 hours at 15-35 ℃, and purifying to obtain a compound shown in formula 1;

preferably, the molar ratio of the 9, 9-dimethylxanthene to the chloro-tert-butane is 1 (2-3); more preferably, the molar weight of the ferric chloride and the 9, 9-dimethyl xanthene is (1-2) to 20;

optionally, the purification comprises the steps of: adding water into the reaction solution, extracting with dichloromethane to obtain an organic phase, drying the organic phase with anhydrous sodium sulfate, removing the organic solvent, separating by silica gel column chromatography with petroleum ether as eluent, and drying.

7. The method for producing an anthracene derivative-based excimer light-emitting material according to claim 3, wherein a synthetic route of the compound represented by formula 3 is as follows:

the compound shown in the formula 3 is prepared by the following method: under an inert atmosphere, putting 9-bromoanthracene, pinacol diboron, potassium acetate and [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride into a reaction vessel, adding 1, 4-dioxane, heating, refluxing, reacting for 8-12 hours, and purifying to obtain a compound shown in a formula 3;

preferably, the molar ratio of the 9-bromoanthracene to the pinacol diboron is 1 (1.5-3); more preferably, the molar weight ratio of the potassium acetate to the 9-bromoanthracene is 2-4: 1; more preferably, the molar weight of the 1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride and the 9-bromoanthracene is (1-2): 20;

optionally, the purification comprises the steps of: cooling the reaction liquid to 15-35 ℃, filtering and collecting filtrate, removing the solvent, separating by using a silica gel column chromatography and using a mixed solvent of petroleum ether and dichloromethane as an eluent, and drying;

preferably, the volume ratio of the petroleum ether to the dichloromethane in the mixed solvent is (3-6): 1.

8. A thin film comprising the anthracene derivative-based excimer light-emitting material according to claim 1, wherein the thin film is prepared by doping the anthracene derivative-based excimer light-emitting material with 1 wt% of a polymethyl methacrylate polymer.

9. Use of the anthracene derivative-based excimer light-emitting material of claim 1 or the thin film of claim 8 for the production of an organic light-emitting diode.

10. Use of the anthracene derivative-based excimer light-emitting material according to claim 1 for the preparation of a security marking; preferably, the anti-counterfeiting mark is an anti-counterfeiting film.

Technical Field

The invention relates to the field of organic photoelectric materials, in particular to an excimer luminescent material based on anthracene derivatives, a preparation method and application thereof.

Background

The anthracene derivative has the characteristics of simple structure, easy synthesis, excellent excimer light-emitting performance and the like, excimer light-emitting refers to the fact that one excited state molecule interacts with another ground state molecule of the same kind to form a dimer with relatively stable energy, emitted light generated through radiation transition shows the characteristics of spectral red shift, broadening and the like compared with single molecule light-emitting, and the anthracene derivative is widely applied to the fields of organic light-emitting diodes (OLEDs), safety anti-counterfeiting, photocatalytic reaction, cell imaging and the like. However, when the double molecules form the excimer, the fluorescence is quenched due to the serious intermolecular pi-pi action, and the light emitting efficiency is affected, so that it is important to ensure a high light emitting quantum yield while the excimer is formed. In the year 1954, it was possible to,and Kasper reported for the first time the excimer emission of pyrene solution systems. Subsequently, excimer emission was also found in the crystal of pyrene, and the excimer was presumed to be a dimer behavior in an excited state by crystal structure analysis. Through the continuous exploration of scientists, similar to pyrene, the phenomenon of anthracene excimer luminescence is reported successively. The Yang soldier professor topic group finds that the anthracene derivative 2-TA-AN crystal shows green light emission of 526nm, the quantum yield reaches 80%, the service life reaches 163.75ns, and the crystal is completely different from deep blue light emission of a dilute solution (the quantum yield is 26% and the fluorescence life is 2.27 ns). Through single crystal structure analysis, the anthracene structure shows discrete anthracene dimer accumulation, and the distance of anthracene units isNot only is beneficial to the formation of the excimer, but also avoids the fluorescence quenching effect brought by the interaction between molecules. Subsequently, a variety of anthracene derivatives were found to have highly efficient, long-lived excimer emission properties.

However, such side-substituted anthracene derivatives often show a high concentration dependence, and only in a high concentration or in a crystalline state can show the properties of an excimer, which greatly limits the practical application of such luminescence. If the monomolecular excimer can emit light, the practical application range of the excimer can be greatly expanded, and the controllability and predictability of the light-emitting performance of the excimer can be improved.

Therefore, it is necessary to develop a compound having a monomolecular excimer light emitting property.

Disclosure of Invention

The present invention has been made to solve at least some of the technical problems occurring in the prior art, and therefore, in a first aspect of the present invention, the present invention provides an anthracene derivative-based excimer light-emitting material having a structural formula as shown in the following formula X2A:

in one or more embodiments of the present invention, the anthracene derivative-based excimer light-emitting material exhibits red-shifted excimer green emission when dissolved in an organic solvent or doped in a PMMA thin film;

preferably, the fluorescence quantum yield of the anthracene derivative-based excimer light-emitting material in a solid state is more than 99.9%;

more preferably, the anthracene derivative-based excimer light-emitting material is at a concentration of 10^-6～10^-2Dissolving mol/L in an organic solvent; the anthracene derivative-based excimer luminescent material is doped in the PMMA film by 0.5-2 wt%;

more preferably, the organic solvent is selected from one or more of tetrahydrofuran, dichloromethane, chloroform, methanol and ethanol.

In a second aspect of the present invention, the present invention provides a method for preparing an anthracene derivative-based excimer light-emitting material according to the first aspect of the invention, wherein the compound represented by the formula X2A is prepared from a compound represented by the formula 2 and a compound represented by the formula 3.

In one or more embodiments of the invention, the reaction of compounds of formula 2 and 3 to prepare compounds of formula X2A is as follows:

the preparation of the compound represented by the formula X2A from the compound represented by the formula 2 and the compound represented by the formula 3 comprises the following steps:

under an inert atmosphere, putting a compound shown as a formula 2, a compound shown as a formula 3, potassium carbonate and dichloro-di-tert-butyl- (4-dimethylaminophenyl) phosphorus palladium (II) into a reaction vessel, adding tetrahydrofuran and water, heating and refluxing for 5-15 hours, and purifying to obtain a compound shown as a formula X2A;

preferably, the molar ratio of the compound shown in the formula 2 to the compound shown in the formula 3 is 1 (2-5); more preferably, the molar ratio of the potassium carbonate to the compound shown in the formula 2 is (2-6): 1; more preferably, the molar ratio of the dichloro-di-tert-butyl- (4-dimethylaminophenyl) palladium (II) phosphate to the compound shown in the formula 2 is (2-8): 100;

in one or more embodiments of the present invention, the purification of the compound of formula 2 and the compound of formula 3 to produce the compound of formula X2A comprises the steps of: cooling the reaction liquid to 15-35 ℃, adding a saturated sodium chloride aqueous solution into the reaction liquid, extracting with dichloromethane to obtain an organic phase, drying the organic phase with anhydrous sodium sulfate, removing the solvent, separating by silica gel column chromatography with a mixed solvent of petroleum ether and dichloromethane as an eluent, and drying;

preferably, the volume ratio of the petroleum ether to the dichloromethane in the mixed solvent is (4-6): 1.

In one or more embodiments of the invention, the compound represented by formula 2 is prepared from a compound represented by formula 1;

the reaction formula for preparing the compound of formula 2 from the compound of formula 1 is as follows:

the preparation of the compound of formula 2 from the compound of formula 1 comprises the following steps:

dissolving the compound shown in the formula 1 in trichloromethane under ice bath, slowly dropwise adding a liquid bromine solution diluted by the trichloromethane, stirring at 15-35 ℃ for reaction for 10-15 hours, and purifying to obtain the compound shown in the formula 2;

preferably, the molar ratio of the compound shown in the formula 1 to liquid bromine is 1 (2-4);

in one or more embodiments of the present invention, in the preparation of the compound of formula 2 from the compound of formula 1, the purification comprises the steps of: adding sodium sulfite aqueous solution into the reaction solution to quench reaction, extracting with dichloromethane to obtain an organic phase, drying the organic phase with anhydrous sodium sulfate, removing the solvent, separating by silica gel column chromatography with petroleum ether as eluent, and drying.

In one or more embodiments of the present invention, the synthetic route of the compound of formula 1 is as follows:

the compound shown in the formula 1 is prepared by the following method: dissolving 9, 9-dimethylxanthene and ferric chloride in dichloromethane in ice bath, adding a tert-butyl chloride solution diluted by dichloromethane, stirring for 10-15 hours at 15-35 ℃, and purifying to obtain a compound shown in formula 1;

preferably, the molar ratio of the 9, 9-dimethylxanthene to the chloro-tert-butane is 1 (2-3); more preferably, the molar weight of the ferric chloride and the 9, 9-dimethyl xanthene is (1-2) to 20; (ii) a

In one or more embodiments of the present invention, the purification process for preparing the compound represented by formula 1 comprises the following steps: adding water into the reaction solution, extracting with dichloromethane to obtain an organic phase, drying the organic phase with anhydrous sodium sulfate, removing the organic solvent, separating by silica gel column chromatography with petroleum ether as eluent, and drying.

In one or more embodiments of the present invention, the synthetic route of the compound represented by formula 3 is as follows:

the compound shown in the formula 3 is prepared by the following method: under an inert atmosphere, putting 9-bromoanthracene, pinacol diboron, potassium acetate and [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride into a reaction vessel, adding 1, 4-dioxane, heating, refluxing, reacting for 8-12 hours, and purifying to obtain a compound shown in a formula 3;

preferably, the molar ratio of the 9-bromoanthracene to the pinacol diboron is 1 (1.5-3); more preferably, the molar weight ratio of the potassium acetate to the 9-bromoanthracene is 2-4: 1; more preferably, the molar weight of the 1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride and the 9-bromoanthracene is (1-2): 20.

In one or more embodiments of the present invention, the purification process for preparing the compound represented by formula 3 comprises the following steps: cooling the reaction liquid to 15-35 ℃, filtering and collecting filtrate, removing the solvent, separating by using a silica gel column chromatography and using a mixed solvent of petroleum ether and dichloromethane as an eluent, and drying;

preferably, the volume ratio of the petroleum ether to the dichloromethane in the mixed solvent is (3-6): 1.

In a third aspect of the present invention, the present invention provides a thin film comprising the anthracene derivative-based excimer light-emitting material according to the first aspect of the present invention, preferably, the thin film is prepared by doping the anthracene derivative-based excimer light-emitting material with 1 wt% of a polymethyl methacrylate polymer.

In a fourth aspect of the present invention, there is provided a use of the anthracene derivative-based excimer light-emitting material of the first aspect of the present invention or the thin film of the third aspect of the present invention for producing an organic light-emitting diode.

In a fifth aspect of the invention, the invention provides an application of the anthracene derivative-based excimer luminescent material of the first aspect of the invention in preparing a false proof mark; preferably, the anti-counterfeiting mark is an anti-counterfeiting film.

Compared with the prior art, the invention has the beneficial effects that:

1. the present invention provides an anthracene derivative-based excimer light-emitting material which has no dependency on concentration and can realize excimer light emission in a dilute solution, as compared with a common excimer material. In addition, the excimer luminescent material based on the anthracene derivative has stable luminescent property and better thermal stability, and can be stably stored in the air without any special range protection.

2. The invention also provides a preparation method of the excimer luminescent material based on the anthracene derivative, which is characterized in that simple reaction is carried out, the reaction conditions are mild, the reaction yield is high, a base unit 9, 9-dimethylxanthene with proper rigidity is adopted, two anthracene units with deep blue luminescence are fixed, the anthracene units are in a dimer mode, the obtained compound realizes red-shifted green emission of the excimer with the wavelength of about 480nm, the quantum yield is close to 100%, and the service life can reach 48 ns.

3. The invention also provides application of the excimer luminescent material based on the anthracene derivative, and the excimer luminescent material based on the anthracene derivative can be used for preparing anti-counterfeiting marks.

4. The invention also provides another application of the anthracene derivative-based excimer luminescent material, the material can realize excimer luminescence in a thin film state, and can be used as a luminescent material in an organic light-emitting diode device.

Drawings

FIG. 1 is a synthesis scheme of an anthracene derivative-based excimer light-emitting material of the present invention;

FIG. 2 is a diagram showing the solution fluorescence emission spectra of the excimer light-emitting material based on an anthracene derivative prepared according to the present invention in comparison with a monomeric anthracene; wherein, the left side of FIG. 2 is fluorescence emission spectrogram of anthracene monomer solution, and the right side of FIG. 2 is fluorescence emission spectrogram of compound solution represented by formula X2A;

FIG. 3 is a fluorescence spectrum and a fluorescence lifetime chart of a single crystal of an excimer light-emitting material based on an anthracene derivative prepared according to the present invention; wherein, the left of FIG. 3 is a fluorescence spectrum of a single crystal of the compound represented by the formula X2A tested in the solid state, and the right of FIG. 3 is a fluorescence lifetime chart of a single crystal of the compound represented by the formula X2A tested in the solid state;

FIG. 4 shows 10 of an anthracene derivative-based excimer light-emitting material prepared by the present invention^-5Green fluorescence of a 1 wt% doped Polymethylmethacrylate (PMMA) film in a solution of Tetrahydrofuran (THF) at 365 nm.

Fig. 5 is a security pattern of the anthracene derivative-based excimer light-emitting material prepared by the present invention.

Detailed Description

The scheme of the invention will be explained with reference to the examples. It will be appreciated by those skilled in the art that the following examples are illustrative of the invention only and should not be taken as limiting the scope of the invention. The examples, where specific techniques or conditions are not indicated, are to be construed according to the techniques or conditions described in the literature in the art or according to the product specifications. The following examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer, by using conventional methods known in the art without specific descriptions, and by using consumables and reagents which were commercially available without specific descriptions. Unless otherwise defined, technical and scientific terms used herein have the same meaning as is familiar to those skilled in the art. In addition, any methods or materials similar or equivalent to those described herein can also be used in the present invention.

Example 1: synthesis of excimer light-emitting Material Compound X2A based on Anthracene derivative

The synthetic route is as follows:

step 1): synthesis of Compound represented by formula 1

The synthetic route is as follows:

the specific steps are as follows: dissolving 9, 9-dimethylxanthene (3.00g,14.30mmol) and anhydrous ferric chloride (0.12g,0.72mmol) in 15mL dichloromethane in an ice bath, diluting tert-butyl chloride (3.68mL,35.75mmol) with 15mL dichloromethane in a constant pressure dropping funnel, dropwise adding into the 9, 9-dimethylxanthene solution in an ice bath, stirring at 15-35 ℃ for 15 hours, after the reaction is finished, adding water into the reaction solution to quench the reaction solution, extracting with dichloromethane, collecting the organic phase, drying with anhydrous sodium sulfate, separating and purifying the crude product by silica gel column chromatography with petroleum ether as an eluent, drying with a vacuum drying oven to obtain a white solid (3.20g, yield 70%), and purifying with anhydrous sodium sulfate¹The structure of the compound is characterized by H NMR, and the compound is confirmed to be the compound 1.¹H NMR(400MHz,CDCl₃,δ):7.40(d,J＝2.2Hz,2H,ArH),7.21(d,J＝2.2Hz,1H,ArH),7.20(d,J＝2.2Hz,1H,ArH),6.96(s,1H,ArH),6.94(s,1H,ArH),1.65(s,6H,-CH₃),1.33(s,18H,-CH₃)。

Step 2): synthesis of Compound 2:

the synthetic route is as follows:

the specific steps are as follows: dissolving a compound (1.00g and 3.10mmol) shown in the formula 1 in 15mL of trichloromethane under ice bath, diluting liquid bromine (0.34mL and 6.50mmol) in the trichloromethane, dropwise adding the diluted liquid bromine (0.34mL and 6.50mmol) into the compound solution shown in the formula 1 by using a constant-pressure dropping funnel, stirring and reacting for 2 hours after the dropwise adding is finished, repeating the dropwise adding process again, dropwise adding the diluted liquid bromine (0.34mL and 6.50mmol) into the reaction solution, and heating to 15-35 ℃ after the dropwise adding is finishedStirring at room temperature for 12 hr, adding sodium sulfite aqueous solution to the reaction solution to quench the reaction, extracting with dichloromethane, collecting organic phase, drying with anhydrous sodium sulfate to obtain crude product, separating and purifying with silica gel column chromatography and petroleum ether as eluent, drying with vacuum drying oven to obtain white solid (1.40g, yield 95%), and adding water to obtain the final product¹The structure of the compound is characterized by H NMR, and the compound is confirmed to be the compound 2.¹H NMR(400MHz,CDCl₃,δ):7.47(d,J＝2.2Hz,2H,ArH),7.33(d,J＝2.2Hz,2H,ArH),1.62(s,6H,-CH₃),1.32(s,18H,-CH₃)。

Step 3): synthesis of Compound 3:

the synthetic route is as follows:

the specific steps are as follows: under a nitrogen atmosphere, 9-bromoanthracene (3.00g,11.67mmol), pinacol diboron (4.44g, 17.52mmol), potassium acetate (2.28g,23.34mmol), [1,1' -bis (diphenylphosphino) ferrocene]Palladium dichloride (0.6g,0.81mmol) was added to the flask, 35mL of previously deoxygenated 1, 4-dioxane was added, and the reaction was refluxed for 12 hours. Filtering the reaction solution, collecting filtrate, separating and purifying the crude product by silica gel column chromatography with mixed solvent of petroleum ether and dichloromethane at volume ratio of (4:1) as eluent, drying with vacuum drying oven to obtain white solid (2.49g, 70%), and purifying with silica gel column chromatography¹The structure of the compound was characterized by H NMR, and it was confirmed that the compound was a compound represented by formula 3.¹H NMR(400MHz,CDCl₃,δ):8.48-8.43(m,3H,ArH),7.99(d,J＝8.2Hz,2H,ArH),7.50-7.42(m,4H,ArH),1.58(s,12H,-CH₃)。

Step 4): synthesis of compound X2A:

the synthetic route is as follows:

the specific steps are as follows: in nitrogenUnder an atmosphere, a compound represented by formula 2 (1.00g,2.08mmol), a compound represented by formula 3 (1.90g,6.24mmol), anhydrous potassium carbonate (1.15g,8.32mmol), 1,1' -bis (diphenylphosphino) ferrocene]Palladium dichloride (0.08g,0.11mmol) was added to the flask, and 25mL of purified, deoxygenated tetrahydrofuran and 5mL of deionized water were added and reacted under reflux for 12 hours. Adding saturated sodium chloride aqueous solution to quench the reaction, extracting with dichloromethane to collect the organic layer, drying with anhydrous sodium sulfate to obtain crude product, separating and purifying with silica gel column chromatography using mixed solvent of petroleum ether and dichloromethane (volume ratio of petroleum ether to dichloromethane is 6:1) as eluent, drying with vacuum drying oven to obtain light yellow solid (1.12g, yield 60%), and purifying with sodium chloride solution¹H NMR、¹³The structure was characterized by C NMR, MS and EA, confirming that this compound was X2A.¹H NMR(400MHz,CDCl₃,δ):7.90(s,2H,ArH),7.59(d,J＝8.4Hz,4H,ArH),7.56(d,J＝2.2Hz,2H,ArH),7.04-6.97(m,10H,ArH),6.74(t,J＝8.0Hz,4H,ArH),1.90(s,6H,-CH₃),1.30(s,18H,-CH₃)；¹³C NMR(100MHz,CDCl₃)δ(ppm):132.11,130.19,129.23,129.01,127.86,125.87,125.36,123.95,123.88,123.44,113.57,100.27,99.99,99.86,35.18,34.57,32.62,31.62.MS(EI,m/z):[M]⁺calcd for:C₅₁H₄₆O,674.35；Found,674.18.Anal.Cacld for C₅₁H₄₆O:C,90.76；H,6.87.Found:C,90.67；H,7.08。

Step 5): preparation of a single crystal of the compound represented by formula X2A: dissolving 15mg of a compound shown as X2A in 3mL of dichloromethane solvent, dropwise adding a small amount of petroleum ether solvent, standing at normal temperature for culturing single crystal, and volatilizing the solvent to obtain blocky green luminescent crystals.

Example 2: performance test of excimer light-emitting Material Compound X2A based on Anthracene derivative

The compound represented by the formula X2A obtained in example 1 and anthracene were each dissolved in an appropriate amount of dichloromethane to prepare 1X 10^-5And (3) testing a fluorescence emission spectrum of the solution in mol/L, wherein the fluorescence emission spectrum of the anthracene monomer solution is shown on the left of the graph 2, and the fluorescence emission spectrum of the compound solution shown in the formula X2A is shown on the right of the graph 2. In the solid stateThe fluorescence spectrum and fluorescence lifetime of the single crystal of the compound represented by the formula X2A were measured, and the results are shown in fig. 3, in which fig. 3 is a graph on the left of the fluorescence spectrum of the single crystal of the compound represented by the formula X2A measured in the solid state, and fig. 3 is a graph on the right of the fluorescence lifetime of the single crystal of the compound represented by the formula X2A measured in the solid state. The compound of formula X2A was formulated at a concentration of 10^-5As a result of irradiating a Tetrahydrofuran (THF) solution of mol/L with 365nm ultraviolet light, it was found that the solution had green fluorescence as shown in FIG. 4, and a single crystal of the compound represented by the formula X2A was doped in polymethyl methacrylate (PMMA) at a ratio of 1 wt% to prepare a thin film, and the film was irradiated with 365nm ultraviolet light, which still exhibited bright green fluorescence, and as a result, as shown in FIG. 4, the excimer light emission with high quantum yield and long lifetime as represented by the compound represented by X2A was expected to be further applied in the field of organic light emitting diodes.

Example 3: application of excimer luminescent material based on anthracene derivative in anti-counterfeiting field

A white powder of the compound of formula X2A was spread on a white filter paper in the form of the abbreviation "WHU" of the university of Wuhan, and a bright green word "WHU" appeared on the filter paper under irradiation of a 365nm ultraviolet lamp. The results are shown in fig. 5, and the results can show that the compound can be used for preparing anti-counterfeiting marks and can be used in the fields of information storage, information transmission and the like.

Although the embodiments of the present invention have been shown and described, it is understood that the above embodiments are illustrative and not restrictive, and that those skilled in the art may change, modify, replace and modify the above embodiments within the scope of the present invention and that they should be included in the protection scope of the present invention.