Preparation and application of organic scintillators containing heterocyclic fused aromatic hydrocarbons and their halides

Abstract

The present invention discloses an organic scintillator of heterocyclic fused aromatic hydrocarbons and their halides, as well as their preparation and application. The organic scintillator comprises a Suzuki coupling reaction to synthesize the heterocyclic fused aromatic hydrocarbon organic scintillator under an inert gas atmosphere, and then protonating the heterocyclic fused aromatic hydrocarbons using hydrogen halide to obtain the heterocyclic fused aromatic hydrocarbon halides. The synthesis method of the present invention is simple, and the required equipment is simple. The obtained heterocyclic fused aromatic hydrocarbon and its halides organic scintillator exhibit strong X-ray fluorescence under X-ray irradiation, can be used for X-ray detection and imaging, and has good resolution, a short decay time, a fast response speed, and strong radiation stability. The organic scintillator can also be applied to flexible imaging. This solves the problems of high production cost, difficult production process, and difficulty in flexible imaging application of inorganic scintillators, as well as the problem that traditional organic scintillator materials have weak X-ray absorption and low radiation luminescence intensity, which hinder their future development.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic scintillators, and specifically relates to an organic scintillator of condensed aromatic hydrocarbons containing heterocycles and their halides, a preparation method thereof, and applications thereof in X-ray imaging or radiation detection. Background Art

[0002] X-ray imaging technology plays a wide range of important roles in medical imaging, security and inspection, industrial testing, aerospace, and other fields. Scintillators are a core component in X-ray imaging equipment, converting high-energy X-ray photons into low-energy ultraviolet or visible light. Currently, inorganic single-crystal scintillators such as NaI:Tl, CsI:Tl, and (Lu,Y)2SiO5 (LYSO) are widely used commercially due to their high light yield and high X-ray absorption coefficient. However, these scintillators have several drawbacks in terms of performance and production. First, the growth temperature of inorganic scintillators is extremely high, such as that of CsI:Tl, which reaches as high as 1700°C. Second, some inorganic scintillators have poor stability. For example, NaI:Tl single crystals are easily damaged by prolonged X-ray irradiation, resulting in a decrease in luminous efficiency. Most importantly, these materials, especially CsI:Tl, are prone to deliquescing in air, which significantly reduces the lifespan of the scintillator single crystal. Furthermore, these materials lack inherent flexibility, making them unsuitable for flexible X-ray detectors and impractical for three-dimensional X-ray imaging.

[0003] Organic scintillators offer significant advantages, including abundant raw material reserves, low cost, excellent processing properties, large-scale fabrication, good biocompatibility, and low toxicity. They hold great potential for application in flexible electronics, particularly in the field of nanostructured electronics. However, traditional organic scintillators, primarily composed of carbon, hydrogen, and nitrogen, exhibit weak X-ray absorption and inefficient exciton utilization, hindering the development of pure organic scintillators. Therefore, developing organic scintillators with superior radioluminescence properties through rational molecular design and preparation methods is of great significance. Summary of the Invention

[0004] In view of the shortcomings of the existing technology, the present invention provides a heterocyclic condensed aromatic hydrocarbon and its halogenated organic scintillator, which is applied in the field of X-ray imaging.

[0005] To achieve the above object, the present invention adopts the following technical solutions:

[0006] One of the purposes of the present invention is to protect a heterocyclic fused aromatic hydrocarbon organic scintillator, whose general structural formula is shown in Formula I, and a heterocyclic fused aromatic hydrocarbon halide organic scintillator, whose general structural formula is shown in Formula II:

[0007]

[0008] In the formula, Ar represents a condensed ring aromatic hydrocarbon selected from substituted or unsubstituted benzene, naphthalene, anthracene, phenanthrene, perylene, pyrene, and fluorene; R is selected from H or an alkyl group containing 1 to 5 carbon atoms; n is a natural number between 0 and 20, and m is a natural number between 0 and 20; X represents halogen F, Cl, Br, and I.

[0009] Furthermore, the general structural formula of the heterocyclic condensed aromatic hydrocarbon organic scintillator is shown in Formula III, and the general structural formula of the heterocyclic condensed aromatic hydrocarbon halide organic scintillator is shown in Formula IV:

[0010]

[0011] In the formula, R, m, n and X are defined the same as in Formula I and Formula II. Preferably, R is H or a C1 alkyl group; m is a natural number between 0 and 3, more preferably 0; n is a natural number between 0 and 3, more preferably 0; and X is Cl, Br, or I. Specifically, the structural formula of the heterocyclic-containing fused aromatic hydrocarbon organic scintillator represented by Formula III can be: The structural formula of the heterocyclic condensed aromatic hydrocarbon halide organic scintillator shown in Formula IV can be

[0012] The second object of the present invention is to protect the preparation method of the heterocyclic fused aromatic hydrocarbon organic scintillator, which is to use compound A and pyridine-4-boronic acid in an inert gas atmosphere. As raw materials, in the presence of base and catalyst, a condensed aromatic hydrocarbon organic scintillator containing heterocyclic ring is prepared by reaction in solvent A.

[0013] Furthermore, the molar ratio of compound A, pyridine-4-boronic acid, base and catalyst used is 15:54:57:1.

[0014] Furthermore, the general structural formula of the compound A is:

[0015]

[0016] Furthermore, the base is one or more of potassium carbonate, sodium carbonate, and cesium carbonate.

[0017] Furthermore, the catalyst is one or more of tetrakis(triphenylphosphine)palladium, 1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride, and bis(triphenylphosphine)palladium dichloride (II).

[0018] Furthermore, the solvent A is tetrahydrofuran, methanol, ethanol, N,N-dimethylformamide, acetonitrile, 1,4-dioxane or a mixture thereof with water.

[0019] Furthermore, the reaction temperature is 70 to 120° C., and the reaction time is 18 to 72 hours.

[0020] A third object of the present invention is to provide a method for preparing the heterocyclic condensed aromatic hydrocarbon halide organic scintillator, which comprises reacting the heterocyclic condensed aromatic hydrocarbon halide organic scintillator with hydrogen halide HX in a solvent B containing or not containing alcohol to obtain the heterocyclic condensed aromatic hydrocarbon halide organic scintillator; specifically, the method comprises:

[0021] (1) When R is H, the heterocyclic fused aromatic organic scintillator is subjected to a protonation reaction with hydrogen halide HX in solvent B to obtain a corresponding product; the reaction temperature is 20 to 60° C., and the reaction time is 2 to 60 minutes;

[0022] (2) When R is a C1-C3 alkyl group, the heterocyclic fused aromatic hydrocarbon organic scintillator is subjected to a solvothermal reaction with hydrogen halide HX in a solvent B containing or not containing alcohol to obtain the corresponding product; the reaction is carried out under high pressure or normal pressure, the reaction temperature is 80-150° C., and the reaction time is 48-96 hours.

[0023] Furthermore, the molar ratio of the heterocyclic-containing condensed aromatic hydrocarbon organic scintillator to the hydrogen halide is 1-3:5-10.

[0024] Furthermore, the alcohol contains 1-5 carbon atoms.

[0025] Furthermore, the solvent B is one or more of N-methylpyrrolidone, acetonitrile, methanol, ethanol, N,N-dimethylformamide, and dimethyl sulfoxide.

[0026] Specifically, a) the preparation method of the above-mentioned formula III-1 is: dissolving 9,10-dibromoanthracene, pyridine-4-boric acid, a base (preferably potassium carbonate) and a catalyst (preferably tetrakistriphenylphosphine palladium) in a solvent (preferably a mixed solution of 1,4-dioxane and water), reacting for 24 to 48 hours to obtain a crude product, and the crude product is separated by silica gel column chromatography (the eluent is preferably a mixed solvent of dichloromethane and petroleum ether); the reaction formula is shown below:

[0027]

[0028] The reaction needs to be deoxygenated and carried out under an inert atmosphere.

[0029] The reaction temperature is 70-120°C, preferably 90-100°C.

[0030] b) The preparation method of the above formula IV-1 to formula IV-3 is: dissolving the obtained substance of formula III-1 in an organic solvent (preferably N-methylpyrrolidone) and reacting with HCl, HBr, and HI respectively; the reaction formula is shown below:

[0031]

[0032] The reaction temperature is 20-60°C, preferably 25-40°C.

[0033] c) The preparation method of the above formula IV-4 is: dissolving the obtained substance of formula III-1 in methanol, adding HBr, and placing it in a high-temperature and high-pressure reactor to react; the reaction formula is as follows:

[0034]

[0035] The reaction temperature is 80-150°C, preferably 110-130°C.

[0036] The fourth object of the present invention is to protect the application of the heterocyclic-containing fused-ring aromatic hydrocarbon and its halide organic scintillator in X-ray imaging or radiation detection.

[0037] The significant advantages of the present invention are:

[0038] The heterocyclic condensed aromatic hydrocarbons and their halogenated organic scintillators provided by the present invention have strong absorption of X-rays and have the advantages of strong radiation luminescence intensity, extremely low detection limit and short response time, high radiation stability, etc. It is an organic scintillator material with excellent performance and can be applied to the field of X-ray imaging and flexible imaging. It solves the problems of high production cost, difficult production process and difficulty in flexible imaging of inorganic scintillators, as well as the problem that traditional organic scintillator materials are hindered in their future development due to their weak X-ray absorption and low radiation luminescence intensity.

[0039] The heterocyclic condensed aromatic hydrocarbons and their halogenated organic scintillators provided by the present invention are low in price, simple in processing technology, can be prepared on a large scale, have good biocompatibility, and have good application prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] Figure 1 This is the hydrogen nuclear magnetic resonance spectrum of the heterocyclic-containing condensed aromatic hydrocarbon organic scintillator prepared in Example 1.

[0041] Figure 2a The figure shows the crystal structure of the heterocyclic fused aromatic halide DPACl prepared in Example 1.

[0042] Figure 2b This is the crystal structure diagram of the heterocyclic-containing fused aromatic halide DPABr prepared in Example 1.

[0043] Figure 2c The crystal structure diagram of the heterocyclic-containing fused-ring aromatic halide DPAI prepared in Example 1.

[0044] Figure 2d Comparison diagram of the crystal structure stacking diagrams of DPA (left) and DPABr (right) prepared in Example 1.

[0045] Figure 2e The crystal structure diagram of the heterocyclic fused aromatic halide DPACH3Br prepared in Example 1.

[0046] Figure 3 This is the X-ray powder diffraction pattern of the heterocyclic-containing condensed aromatic hydrocarbon halide organic scintillator prepared in Example 1.

[0047] Figure 4 This is the ultraviolet fluorescence spectrum of the heterocyclic-containing condensed aromatic hydrocarbon and its halogenated organic scintillator prepared in Example 1.

[0048] Figure 5 This is an X-ray fluorescence spectrum of the heterocyclic-containing condensed aromatic hydrocarbon and its halogenated organic scintillator prepared in Example 1.

[0049] Figure 6 Graphs showing X-ray fluorescence spectra of the heterocyclic-containing fused aromatic hydrocarbon and its halogenated organic scintillators prepared in Example 1 under different radiation doses.

[0050] Figure 7 This is a linear response diagram of the heterocyclic-containing condensed aromatic hydrocarbon and its halogenated organic scintillator prepared in Example 1 under different radiation doses.

[0051] Figure 8 This is a graph showing the continuous irradiation stability of the heterocyclic-containing condensed aromatic hydrocarbon and its halogenated organic scintillator prepared in Example 1.

[0052] Figure 9 This is an X-ray imaging diagram of the heterocyclic-containing condensed aromatic hydrocarbon halide organic scintillator (Formula IV-2) prepared in Example 1. DETAILED DESCRIPTION

[0053] Unless otherwise specified, the experimental methods used in the following examples are conventional methods.

[0054] Unless otherwise specified, the materials and reagents used in the following examples can be obtained from commercial sources.

[0055] The present invention can adopt conventional techniques of organic chemistry within the skill of the art. In the following examples, efforts have been made to ensure the accuracy of the numbers used (including amounts, temperatures, reaction times, etc.), but some experimental errors and deviations should be taken into account. The temperatures used in the following examples (in degrees Celsius) are expressed in ° C, and the pressures are atmospheric pressure or near atmospheric pressure. All solvents are purchased with analytical purity, and all reactions are carried out under an argon inert atmosphere. Unless otherwise noted, all reagents are commercially available.

[0056] Example 1 Synthesis of 9,10-di(pyridin-4-yl)anthracene (Formula III-1), 4,4'-(anthracene-9,10-diyl)bis(pyridin-1-ium) chloride (Formula IV-1), 4,4'-(anthracene-9,10-diyl)bis(pyridin-1-ium) bromide (Formula IV-2), 4,4'-(anthracene-9,10-diyl)bis(pyridin-1-ium) iodide (Formula IV-3), and 4,4'-(anthracene-9,10-diyl)bis(1-methylpyridin-1-ium) bromide (Formula IVIII-4)

[0057] (1) Synthesis of 9,10-di(pyridin-4-yl)anthracene (Formula III-1)

[0058]

[0059] Accurately weigh pyridine-4-boronic acid (18 mmol, 2.200 g) and 9,10-dibromoanthracene (5 mmol, 1.700 g) in a clean 100 ml flask and mix. Tetrakis(triphenylphosphine)palladium catalyst (0.33 mmol, 381.6 mg) and approximately 40 ml of N,N-dimethylformamide are then added. K₂CO₃ (18.8 mmol, 2.598 g) is dissolved in 10 ml of water and added to the flask. The oxygen in the flask is then purged with argon. The mixture is refluxed under condensation at 95°C for 24 hours under an argon atmosphere. After completion of the reaction, the solvent is removed by rotary evaporation. The resulting solid is dissolved in 100 ml of dichloromethane, filtered, and washed twice with 25 ml of a Na₂CO₃ solution (containing 5.500 g of Na₂CO₃). The two extracts were combined and dried over anhydrous Na2SO4. The dichloromethane was removed by rotary evaporation and the resulting solid was separated and purified by silica gel column using a mixed solvent of petroleum ether and dichloromethane (1:2, v / v) as eluent to obtain about 1.162 g (yield 72%) of a light yellow solid product.

[0060] Figure 1 The H NMR spectrum of the obtained product is shown in Figure 2, and its structure is characterized as follows: 1 H NMR (500MHz, CDCl3, δ): 8.87 (m, 4H), 7.60 (m, 4H), 7.44 (m, 4H), 7.39 (m, 4H).

[0061] (2) Synthesis of 4,4'-(anthracene-9,10-diyl)bis(pyridin-1-ium) chloride (Formula IV-1)

[0062]

[0063] 200 mg of 9,10-di(pyridin-4-yl)anthracene was placed in a 25 ml beaker, and 15 ml of N-methylpyrrolidone was added and stirred thoroughly to dissolve it completely. HCl was then added dropwise to the beaker at room temperature until the mixture reached 0.5 ml. After stirring for 5 minutes, the mixture was filtered and air-dried to obtain 214.1 mg of 4,4'-(anthracene-9,10-diyl)bis(pyridin-1-ium) chloride (yield 88%).

[0064] (3) Synthesis of 4,4'-(anthracene-9,10-diyl)bis(pyridin-1-ium) bromide (Formula IV-2)

[0065]

[0066] 200 mg of 9,10-di(pyridin-4-yl)anthracene was placed in a 25 ml beaker, and 15 ml of N-methylpyrrolidone was added and stirred thoroughly to dissolve it completely. HBr was then added dropwise to the beaker at room temperature until it reached 0.5 ml. After stirring thoroughly for 5 minutes, the mixture was filtered and air-dried to obtain 266.6 mg of 4,4'-(anthracene-9,10-diyl)bis(pyridin-1-ium) bromide (yield 90%).

[0067] (4) Synthesis of 4,4'-(anthracene-9,10-diyl)bis(pyridin-1-ium) iodide (Formula IV-3)

[0068]

[0069] 200 mg of 9,10-di(pyridin-4-yl)anthracene was placed in a 25 ml beaker, and 15 ml of N-methylpyrrolidone was added and stirred thoroughly to dissolve it completely. HI was then added dropwise to the beaker at room temperature until the mixture reached 0.8 ml. After stirring thoroughly for 5 minutes, the mixture was filtered and air-dried to obtain 300.9 mg of 4,4'-(anthracene-9,10-diyl)bis(pyridin-1-ium) iodide (yield 85%).

[0070] (5) Synthesis of 4,4'-(anthracene-9,10-diyl)bis(1-methylpyridin-1-ium) bromide (Formula IV-4)

[0071]

[0072] 200 mg of 9,10-di(pyridin-4-yl)anthracene was placed in a high-temperature, high-pressure reactor. 5 ml of methanol was added to the reactor and stirred thoroughly. HBr was then added to the reactor until the mixture reached 0.5 ml. After stirring for 15 minutes, the reactor was tightened and placed in an oven. The reaction was carried out at 130°C for 48 hours. The temperature was then lowered to room temperature over 12 hours. Green crystals precipitated in the reactor, namely 4,4'-(anthracene-9,10-diyl)bis(1-methylpyridin-1-ium) bromide (yield 70%).

[0073] X-ray single crystal diffraction test of the product obtained in Example 2 and Example 1

[0074] The crystals of formula III-1 (DPA), formula IV-1 (DPACl), formula IV-2 (DPABr), and formula IV-3 (DPAI) prepared in Example 1 were obtained by a volatilization method, and the crystals of formula IV-4 (DPACH3Br) prepared in Example 1 were obtained by a solvent thermal method. Then, the five materials were subjected to single crystal diffraction using a Mo target X-ray single crystal diffractometer to obtain their crystal structures. The crystal parameters are shown in Tables 1 and 2. The test results are shown in Tables 1 and 2. Figures 2a-2e shown.

[0075] Table 1 Crystal parameters of organic single crystal scintillators of formula III-1 (DPA), formula IV-1 (DPACl), and formula IV-2 (DPABr)

[0076]

[0077]

[0078] a R1=∑││F0│-│F c ││ / ∑│F0│. b wR2={∑[w(F0 2 -F c ) 2 ] / ∑[w(F0 2 ) 2 ]} 1 / 2

[0079] Table 2 Crystal parameters of organic single crystal scintillators Formula IV-3 (DPAI) and Formula IV-4 (DPACH3Br)

[0080]

[0081]

[0082] The crystal structures of the three halides of Formula IV-1 (DPACl), Formula IV-2 (DPABr), and Formula IV-3 (DPAI) are isomorphous. Compared to the unprotonated Formula III-1 (DPA), the incorporation of halogens improves the sample's absorption of X-rays. Furthermore, the introduction of halogens furthers the distance between the two pyridine-containing heterocyclic aromatic hydrocarbons, reducing the π-π stacking of the two pyridine-containing heterocyclic aromatic hydrocarbons and enhancing the radiative luminescence of the halides. Therefore, these pyridine-containing heterocyclic aromatic hydrocarbon halides are very advantageous as scintillators.

[0083] Example 3. X-ray powder diffraction test of the product obtained in Example 1

[0084] Weigh 50 mg each of the halides of formula IV-1 (DPACl), formula IV-2 (DPABr), and formula IV-3 (DPAI) prepared in Example 1, place them on silicon plate sample slots, and test the above samples using an X-ray powder diffractometer. The test results are as follows: Figure 3 shown.

[0085] Depend on Figure 3 It can be seen that by comparing the test results with the powder test results simulated using a single crystal structure, the test data are consistent with the computer simulation data, indicating that Formula IV-1, Formula IV-2, and Formula IV-3 all have very high purity.

[0086] Example 4. Ultraviolet fluorescence spectrum test of the product obtained in Example 1

[0087] Weigh 50 mg each of formula III-1 (DPA), formula IV-1 (DPACl), formula IV-2 (DPABr), and formula IV-3 (DPAI) prepared in Example 1, place them in solid sample tanks, and perform ultraviolet fluorescence spectrum test on the above samples using FLS980 fluorescence spectrometer. The test results are as follows: Figure 4 shown.

[0088] Depend on Figure 4 It can be seen that the emission peak of formula III-1 (DPA) is around 457nm, and the emission peaks of the halides of formula IV-1 (DPACl), formula IV-2 (DPABr), and formula IV-3 (DPAI) are around 485nm, indicating that the luminescence of these four materials is in the visible light region, which is conducive to their luminescence being captured by the camera as scintillator materials in the X-ray imaging system.

[0089] Example 5. X-ray fluorescence test of the product obtained in Example 1

[0090] The FS 5 fluorescence spectrometer was connected to a 4W radiation source. The voltage of the radiation source was set to 50 kV and the current was set to 79 μA, which means the radiation dose rate was 278 μGy·s. -1 The radiation fluorescence of five samples of formula III-1 (DPA), formula IV-1 (DPACl), formula IV-2 (DPABr), formula IV-3 (DPAI), and formula IV-4 (DPACH3Br) were tested respectively, and the four materials were compared with the commercial inorganic scintillator material bismuth germanium oxide (BGO). The test results are as follows Figure 5 shown.

[0091] Depend on Figure 5It can be seen that Formula III-1 (DPA), Formula IV-1 (DPACl), Formula IV-2 (DPABr), and Formula IV-3 (DPAI) all have strong luminescence and can be used as scintillator materials. The luminescence intensity of the four materials is Formula IV-2 (DPABr) > Formula IV-1 (DPACl) > Formula III-1 (DPA) > Formula IV-3 (DPAI). It is worth mentioning that the luminescence intensity of Formula IV-2 (DPABr) is even much higher than that of the inorganic scintillator material bismuth germanium oxide (BGO), indicating that Formula IV-2 (DPABr) is the most suitable organic scintillator material and is expected to be used in commercial applications.

[0092] Example 6: X-ray fluorescence spectrometry test of the product obtained in Example 1 at different radiation dose rates

[0093] The FS 5 fluorescence spectrometer was used in conjunction with a 4W radiation source. The radiation dose rate was varied by changing the voltage and current of the radiation source. The radiation dose rates were 4.583μGy·s -1 , 9.461μGy·s -1 , 11.915μGy·s -1 , 17.375μGy·s -1 、34.75μGy·s -1 , 69.5μGy·s -1 , 104.25μGy·s -1 , 139μGy·s -1 、173.75μGy·s -1 , 208.5μGy·s -1 , 243.25μGy·s -1 , 278μGy·s -1 The radiation fluorescence of the following formula III-1 (DPA), formula IV-1 (DPACl), formula IV-2 (DPABr), and formula IV-3 (DPAI) is tested as follows Figure 6 shown.

[0094] Figure 6 The results show that these four materials have good linear responses to changes in X-ray dose rate.

[0095] Example 7. Calculation of the detection limit of the product obtained in Example 1

[0096] The sensitivity of scintillator materials to X-ray detection is an important indicator of their performance. High sensitivity requires high luminescence intensity, which is an important basis for reducing X-ray detection dose. The limit of detection (LOD) is the average value of the background signal generated by the blank sample plus three times the standard deviation of the mean. The calculation formula for the limit of detection is used for calculation, and the calculation results are shown in the attached figure. Figure 7shown.

[0097] Depend on Figure 7 It can be seen that the detection limit of formula III-1 (DPA) for X-rays is 106.11nGy·s -1 The detection limit of formula IV-1 (DPACl) for X-rays is 30.32 nGy·s -1 The detection limit of formula IV-2 (DPABr) for X-rays is 11.55 nGy·s -1 The detection limit of formula IV-3 (DPAI) for X-rays is 214.2 nGy·s -1 The radiation dose commonly used in medical treatment is about 5500nGy·s -1 Formula III-1, Formula IV-1, Formula IV-2, and Formula IV-3 are all far below the current medical level, especially Formula IV-2 (DPABr), the detection limit of this material is only 1 / 467 of the current medical level.

[0098] Example 8. Radiation stability test of the product obtained in Example 1

[0099] In order for scintillator materials to be applied in practice, in addition to having excellent radioluminescence properties, the study of their stability is crucial. Therefore, the radiation stability of scintillator materials is also an important evaluation indicator. Weigh 50 mg each of Formula III-1 (DPA), Formula IV-1 (DPACl), Formula IV-2 (DPABr), and Formula IV-3 (DPAI); use a 4W radiation source, at a voltage of 50 kV, a current of 79 μA, and a radiation dose rate of 278 μGy·s. -1 Under the conditions of , formula III-1, formula IV-1, formula IV-2, and formula IV-3 were irradiated continuously for 1800s to determine the radiation stability of formula III-1 (DPA), formula IV-1 (DPACl), formula IV-2 (DPABr), and formula IV-3 (DPAI). The test results are as follows Figure 8 shown.

[0100] like Figure 8 As shown, formula III-1 (DPA) still has strong radioluminescence after irradiation, and its radioluminescence intensity is 97.6% of the initial value. The intensity of formula IV-1 (DPACl) after irradiation is 98.2% of the initial value. Formula IV-2 (DPABr) has the best radiation resistance. After irradiation for 1800s, its radioluminescence intensity can still maintain 98.5% of the initial value. The intensity of formula IV-3 (DPAI) after irradiation is 97.0% of the initial value.

[0101] Example 9: Application of X-ray imaging of the halide of formula IV-2 (DPABr) obtained in Example 1

[0102] In X-ray imaging systems, scintillator materials play a vital role. Formula IV-2 (DPABr) has excellent scintillation properties and can be used to make flexible films for X-ray imaging. Specifically, Formula IV-2 (DPABr) is first ground into nanometer-level uniform particles, and then mixed with silicone-based elastic glue SYLGARDTM184 (PDMS) to form a flexible scintillator film for X-ray imaging of objects. The imaging results are shown in Figure 9 .

[0103] like Figure 9 As shown, the halide of formula IV-2 is used to prepare flexible films, which exhibit good X-ray imaging properties.

[0104] The above description is only a preferred embodiment of the present invention. All equivalent changes and modifications made according to the scope of the patent application of the present invention should fall within the scope of the present invention.

Claims

1. Use of a heterocyclic condensed aromatic hydrocarbon halide organic scintillator in the preparation of an X-ray imaging product or a radiation detection product, characterized in that: The structural formula of the heterocyclic-containing condensed aromatic hydrocarbon halide organic scintillator is any one of the following formulae: 。

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