Preparation method and application of a pure organic X-ray scintillator material

Abstract

The present application discloses a preparation method and application of a pure organic X-ray scintillator material, belonging to the field of optical functional materials. The scintillator material contains a phenoselenazine unit, and the scintillator material is one of,,,, or. The scintillator material of the present invention realizes the regulation of the spatial position of heavy atoms by adjusting the position of methyl substituents, thereby realizing the regulation of X-ray radiation luminescence properties. Compared with traditional inorganic scintillator materials, the preparation method of the scintillator material of the present invention is simple and easy to obtain, has a low cost, and has strong processability. After the scintillator material is made into a glass state, clear imaging under X-rays is achieved, and it has certain application potential in the fields of medical X-ray imaging and security inspection.

Description

Technical Field

[0001] The present invention relates to the field of optical functional materials, and particularly relates to a preparation method and application of a pure organic X-ray scintillator material. Background Art

[0002] Due to heavy element components, X-ray response materials with large X-ray attenuation coefficients have important applications in biological imaging, radiotherapy, and non-destructive testing. Traditional X-ray response materials include non-emissive radiopaque contrast agents (e.g., iodixanol and iopromide) and ceramic scintillators, which can convert high-energy X-ray beams into low-energy visible photons. All X-ray scintillators reported in existing research are limited to inorganic phosphors or organometallic complexes containing heavy metals.

[0003] Metal-free organic phosphors have inherent advantages as scintillators, such as abundant resource supply, high mechanical flexibility, easy processing, and large-area manufacturing; however, weak X-ray absorption and inefficient exciton utilization have hindered the development of organic molecular scintillators. Organic phosphors are mainly composed of light atoms such as carbon, hydrogen, and nitrogen, and have weak absorption of X-rays (attenuation coefficient μ ∝ Z 4 ). In addition, the weak spin-orbit coupling of traditional organic phosphors can only produce fluorescence of singlet excitons after irradiation. In principle, due to the dark state characteristics of triplet excitons in metal-free organic phosphors, about 75% of the excitons are not well utilized.

[0004] At room temperature, bright triplet excitons in organic light-emitting materials can produce phosphorescence. One strategy to achieve room temperature phosphorescence is to promote the intersystem crossing process (ISC) through heavy halogen atoms or aromatic carbonyl groups. It should be noted that the ISC rate constant (k ISC ) is proportional to the eighth power of the atomic number 30 (k ISC ∝ Z 8 ), indicating that heavy atoms can effectively populate triplet excitons. Another strategy is to construct a rigid environment through crystal engineering, host-guest doping, or polymerization to suppress non-radiative energy dissipation. Due to enhanced spin-orbit coupling, halogen atoms can effectively harvest triplet excitons.

[0005] X-ray scintillators are inseparable from phosphorescence. Some studies have regulated the relative positions of heavy atoms and chromophores by changing the substitution positions or the number of substituents of halogen atoms, thereby achieving the regulation of phosphorescent properties. Some studies have shown that the spatial positions of halogen atoms can be indirectly regulated by introducing sterically hindered groups, determining the positions of specific halogen atoms, and adjusting the positions of sterically hindered groups, thereby achieving the regulation of phosphorescent performance. However, currently, in both the field of phosphorescence and organic X-ray scintillators, the in-depth mechanism of the influence of halogen atoms on luminescent properties remains unknown.

[0006] In view of this, it is indeed necessary to provide a technical solution to the above problems. Summary of the invention

[0007] The purpose of the present invention is to overcome the deficiencies of the prior art and provide a preparation method and application of a pure organic X-ray scintillator material.

[0008] According to one aspect of the present invention, a pure organic X-ray scintillator material is provided, wherein the scintillator material contains a pheneselenazine unit. , , , , or One of them.

[0009] According to a second aspect of the present invention, a method for preparing the pure organic X-ray scintillator material is proposed, and the preparation method is as follows:

[0010] S1. Under a nitrogen atmosphere, pheneselenazine, a base, a palladium catalyst and tri-tert-butylphosphine tetrafluoroborate are first dissolved in a toluene solution to form a mixed solution, which is then heated to 90° C. and refluxed for 0.5 h;

[0011] S2. Under a nitrogen atmosphere, the mixed solution is added into a toluene solution containing halogenated benzene, heated to 90° C. and refluxed for 5 h to obtain a pure organic X-ray scintillator material.

[0012] Furthermore, the base is potassium tert-butoxide or sodium tert-butoxide.

[0013] Furthermore, the palladium catalyst is palladium acetate or tris dibenzylideneacetone dipalladium.

[0014] Furthermore, the halogenated benzene is any one of 1-bromo-4-iodobenzene, 2-bromo-5-iodotoluene, 5-bromo-2-iodotoluene, 1-bromo-3-iodobenzene, 2-bromo-4-iodotoluene or 2-bromo-6-iodotoluene.

[0015] Further, the structural formula of the 1-bromo-4-iodobenzene is The structural formula of the 2-bromo-5-iodotoluene is , the structural formula of the 5-bromo-2-iodotoluene is , the structural formula of the 1-bromo-3-iodobenzene is , the structural formula of the 2-bromo-4-iodotoluene is , the structural formula of the 2-bromo-6-iodotoluene is .

[0016] Furthermore, the structural formula of the pheneselenazine is .

[0017] Furthermore, the molar ratio of the pheneselenazine, the base, the palladium catalyst and tri-tert-butylphosphine tetrafluoroborate is 5: (5-7): (0.2-0.5): (0.2-0.5).

[0018] Furthermore, the molar ratio of the phenoselenazine to the halogenated benzene is 5:(5-7).

[0019] According to a third aspect of the present invention, an application of the pure organic X-ray scintillator material in the field of medical X-ray imaging and security inspection is proposed.

[0020] Beneficial effects of the present invention:

[0021] The pure organic X-ray scintillator material provided by the present invention adjusts the position of the methyl substituent, resulting in different steric hindrance effects, affecting the relative position of the heavy atom and the chromophore, thereby achieving the regulation of the performance of the scintillator material, so that the scintillator material exhibits different radioluminescence properties. Compared with traditional inorganic scintillator materials, the preparation method of the pure organic X-ray scintillator material provided by the present invention is simple, low in cost, and has strong processability. After the scintillator material is made into a glassy state, it can achieve clear imaging under X-rays, providing material support for the field of X-ray imaging. The scintillator material has certain application potential in the field of medical X-ray imaging and security inspection. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 is a nuclear magnetic resonance hydrogen spectrum of the scintillator material of formula (I) described in the embodiment of the present invention;

[0023] Figure 2 is a nuclear magnetic resonance hydrogen spectrum of the scintillator material of formula (II) described in the embodiment of the present invention;

[0024] Figure 3 is a nuclear magnetic resonance hydrogen spectrum of the scintillator material of formula (III) described in the embodiment of the present invention;

[0025] Figure 4 is a nuclear magnetic resonance hydrogen spectrum of the scintillator material of formula (IV) described in the embodiment of the present invention;

[0026] Figure 5 is a hydrogen nuclear magnetic resonance spectrum of the scintillator material of formula (V) described in an embodiment of the present invention;

[0027] Figure 6 is a nuclear magnetic resonance hydrogen spectrum of the scintillator material of formula (VI) described in an embodiment of the present invention;

[0028] Figure 7 Graph showing the test results of the photophysical properties of the scintillator materials of formula (I), formula (II) and formula (III) described in the embodiments of the present invention;

[0029] Figure 8 These are the test result graphs of the photophysical properties of the scintillator materials of formulas (IV), (V), and (VI) in the embodiments of the present invention;

[0030] Figure 9 This is the radiation emission spectrum graph of the scintillation material in the embodiments of the present invention under X-ray stimulation;

[0031] Figure 10 This is the result graph of the X-ray detection limit of the scintillator material of formula (II) in the embodiments of the present invention;

[0032] Figure 11 This is the imaging image of the scintillator material of formula (II) in the glassy state in the embodiments of the present invention;

[0033] Figure 12 This is the modulation transfer function graph presented by the scintillator material of formula (II) in the glassy state in the embodiments of the present invention. Detailed implementation manners

[0034] The following further elaborates on the present application in conjunction with the drawings and embodiments. It can be understood that the specific embodiments described herein are only used to explain the relevant invention and not to limit the invention. Additionally, it should be noted that for the sake of description, only the parts related to the relevant invention are shown in the drawings.

[0035] It should be noted that, without conflict, the embodiments in the present application and the features in the embodiments can be combined with each other. The following will elaborate on the present application in detail with reference to the drawings and embodiments.

[0036] In view of the fact that current X-ray scintillators are all limited to inorganic fluorescent powders or organometallic complexes containing heavy metals, and the in-depth mechanism of the influence of halogen atoms on luminescence performance is still unknown. Therefore, the first object of the present invention is to propose a pure organic X-ray scintillator material, which realizes the regulation of the spatial position of heavy atoms, thereby realizing the regulation of X-ray radiation luminescence properties.

[0037] The second object of the present invention is to propose a preparation method according to the pure organic X-ray scintillator material, which has a simple preparation method, low cost, and strong processability.

[0038] The third object of the present invention is to propose an application of the pure organic X-ray scintillator material in the fields of medical X-ray imaging and security inspection.

[0039] Example 1: Preparation of the scintillator material of formula (I)

[0040] Take 1.24g (5mmol) of pheneselenazine, 1.70g (6mmol) of sodium tert-butoxide (t-BuONa), 0.229g (0.25mmol) of tris dibenzylideneacetone palladium (Pd(dba) 2 ) and 0.073 g (0.25 mmol) of tri-tert-butylphosphine tetrafluoroborate (P(t-Bu) 3 HBF 4 ), add 40 ml toluene to dissolve under nitrogen atmosphere, heat to 90℃ and reflux for 0.5h. Take 1-bromo-4-iodobenzene, 1.69g (6mmol), dissolve in 20ml toluene under nitrogen atmosphere, heat to 90℃ and reflux. Add a series of pheneselenazine solutions dropwise and reflux at 90℃ for 5h. Cool to room temperature, extract with ethyl acetate and saturated brine, retain the organic phase, add anhydrous magnesium sulfate to dry, filter, heat and evaporate to remove excess solvent to obtain a crude product, use column chromatography (pure petroleum ether) to obtain the scintillator material of formula (Ⅰ), use dichloromethane and ethanol for recrystallization, and obtain a product mass of 0.62g with a yield of 31%. The specific preparation reaction formula is as follows:

[0041]

[0042] The scintillator material of formula (I) is characterized by a nuclear magnetic resonance spectrum. Figure 1 Shown: 1HNMR (500 MHz, DMSO-d6) δ 7.54 (dd, J = 14.3, 8.2 Hz, 4H), 7.24 (t, J = 7.7Hz, 2H), 7.10 (t, J = 7.4 Hz, 2H), 7.04 (d, J = 8.8 Hz, 2H), 6.99 (d, J = 8.0Hz, 2H).

[0043] Example 2: Preparation of scintillator material of formula (II)

[0044] Take 1.24g (5mmol) of pheneselenazine, 1.70g (6mmol) of sodium tert-butoxide (t-BuONa), 0.229g (0.25mmol) of tris dibenzylideneacetone palladium (Pd(dba) 2 ) and 0.073 g (0.25 mmol) of tri-tert-butylphosphine tetrafluoroborate (P(t-Bu) 3 HBF 4), add 40 ml toluene to dissolve under nitrogen atmosphere, heat to 90℃ and reflux for 0.5h. Take another 1.79g (6mmol) of 2-bromo-5-iodotoluene, dissolve in 20ml toluene under nitrogen atmosphere, heat to 90℃ and reflux. Add a series of pheneselenazine solutions dropwise and reflux at 90℃ for 5h. Cool to room temperature, extract with ethyl acetate and saturated brine, retain the organic phase, add anhydrous magnesium sulfate to dry, filter, heat and evaporate to remove excess solvent to obtain a crude product, use column chromatography (pure petroleum ether) to obtain the scintillator material of formula (II), use dichloromethane and ethanol for recrystallization, and obtain a product mass of 0.71g with a yield of 34%. The specific preparation reaction formula is as follows:

[0045]

[0046] The scintillator material of formula (II) is characterized by a nuclear magnetic resonance spectrum. Figure 2 Shown: 1HNMR (500 MHz, DMSO-d6) δ 7.64 (d, J = 8.5 Hz, 1H), 7.45 (d, J = 7.4 Hz, 2H),7.21 – 7.14 (m, 3H), 7.04 (t, J = 7.4 Hz, 2H), 6.96 (dd, J = 8.5, 2.2 Hz,1H), 6.84 (d, J = 8.0 Hz, 2H), 2.32 (s, 3H).

[0047] Example 3: Preparation of scintillator material of formula (III)

[0048] Take 1.24g (5mmol) of pheneselenazine, 1.70g (6mmol) of sodium tert-butoxide (t-BuONa), 0.229g (0.25mmol) of tris dibenzylideneacetone palladium (Pd(dba) 2 ) and 0.073 g (0.25 mmol) of tri-tert-butylphosphine tetrafluoroborate (P(t-Bu) 3 HBF 4), add 40 ml toluene to dissolve under nitrogen atmosphere, heat to 90℃ and reflux for 0.5h. Take another 1.79g (6mmol) of 2-bromo-5-iodotoluene, dissolve in 20ml toluene under nitrogen atmosphere, heat to 90℃ and reflux. Add a series of pheneselenazine solutions dropwise and reflux at 90℃ for 5h. Cool to room temperature, extract with ethyl acetate and saturated brine, retain the organic phase, add anhydrous magnesium sulfate to dry, filter, heat and evaporate to remove excess solvent to obtain a crude product, use column chromatography (pure petroleum ether) to obtain the scintillator material of formula (III), use dichloromethane and ethanol for recrystallization, and obtain a product mass of 0.44g with a yield of 21%. The specific preparation reaction formula is as follows:

[0049]

[0050] The scintillator material of formula (III) is characterized by a nuclear magnetic resonance spectrum. Figure 3 Shown: 1HNMR (500 MHz, DMSO-d6) δ 7.78 (s, 1H), 7.67 (d, J = 8.3 Hz, 1H), 7.44 (d, J =8.3 Hz, 1H), 7.24 (d, J = 7.5 Hz, 2H), 6.96 (s, 2H), 6.86 (t, J = 7.3 Hz, 2H), 6.18 (d, J = 8.1 Hz, 2H), 2.12 (s, 3H).

[0051] Example 4: Preparation of scintillator material of formula (IV)

[0052] Take 1.24g (5mmol) of pheneselenazine, 1.70g (6mmol) of sodium tert-butoxide (t-BuONa), 0.229g (0.25mmol) of tris dibenzylideneacetone palladium (Pd(dba) 2 ) and 0.073 g (0.25 mmol) of tri-tert-butylphosphine tetrafluoroborate (P(t-Bu) 3 HBF 4), add 40 ml toluene to dissolve under nitrogen atmosphere, heat to 90℃ and reflux for 0.5h. Take another 1.69g (6mmol) of 1-bromo-4-iodobenzene, dissolve in 20ml toluene under nitrogen atmosphere, heat to 90℃ and reflux. Add a series of pheneselenazine solutions dropwise and reflux at 90℃ for 5h. Cool to room temperature, extract with ethyl acetate and saturated brine, retain the organic phase, add anhydrous magnesium sulfate to dry, filter, heat and evaporate to remove excess solvent to obtain a crude product, use column chromatography (pure petroleum ether) to obtain the scintillator material of formula (IV), use dichloromethane and ethanol for recrystallization, and obtain a product mass of 0.51g with a yield of 25%. The specific preparation reaction formula is as follows:

[0053]

[0054] The scintillator material of formula (IV) is characterized by a nuclear magnetic resonance spectrum. Figure 4 Shown: 1HNMR (500 MHz, DMSO-d6) δ 7.62 (d, J = 7.5 Hz, 2H), 7.33 (t, J = 7.4 Hz, 2H), 7.22 (ddt, J = 21.7, 15.0, 7.6 Hz, 6H), 7.08 (s, 1H), 6.96 (d, J = 7.6 Hz, 1H).

[0055] Example 5: Preparation of scintillator material of formula (V)

[0056] Take 1.24g (5mmol) of pheneselenazine, 1.70g (6mmol) of sodium tert-butoxide (t-BuONa), 0.229g (0.25mmol) of tris dibenzylideneacetone palladium (Pd(dba) 2 ) and 0.073 g (0.25 mmol) of tri-tert-butylphosphine tetrafluoroborate (P(t-Bu) 3 HBF 4 ), add 40 ml toluene to dissolve under nitrogen atmosphere, heat to 90℃ and reflux for 0.5h. Take another 1.79g (6mmol) of 2-bromo-4-iodotoluene, dissolve in 20ml toluene under nitrogen atmosphere, heat to 90℃ and reflux. Add a series of pheneselenazine solutions dropwise and reflux at 90℃ for 5h. Cool to room temperature, extract with ethyl acetate and saturated brine, retain the organic phase, add anhydrous magnesium sulfate to dry, filter, heat and evaporate to remove excess solvent to obtain a crude product, use column chromatography (pure petroleum ether) to obtain the scintillator material of formula (V), use dichloromethane and ethanol for recrystallization, and obtain a product mass of 0.40g with a yield of 18%. The specific preparation reaction formula is as follows:

[0057]

[0058] The scintillator material of formula (V) is characterized by a nuclear magnetic resonance spectrum. Figure 5 Shown: 1HNMR (500 MHz, DMSO-d6) δ 7.48 (d, J = 7.7 Hz, 2H), 7.41 (d, J = 8.3 Hz, 1H), 7.34 (d, J = 2.3 Hz, 1H), 7.20 (t, J = 7.7 Hz, 2H), 7.11 (dd, J = 8.3, 2.3Hz, 1H), 7.06 (t, J = 7.5 Hz, 2H), 6.87 (d, J = 8.1 Hz, 2H), 2.35 (s, 3H).

[0059] Example 6: Preparation of scintillator material of formula (VI)

[0060] Take 1.24g (5mmol) of pheneselenazine, 1.70g (6mmol) of sodium tert-butoxide (t-BuONa), 0.229g (0.25mmol) of tris dibenzylideneacetone palladium (Pd(dba) 2 ) and 0.073 g (0.25 mmol) of tri-tert-butylphosphine tetrafluoroborate (P(t-Bu) 3 HBF 4 ), add 40 ml toluene to dissolve under nitrogen atmosphere, heat to 90℃ and reflux for 0.5h. Take another 1.79g (6mmol) of 2-bromo-6-iodotoluene, dissolve in 20ml toluene under nitrogen atmosphere, heat to 90℃ and reflux. Add a series of pheneselenazine solutions dropwise and reflux at 90℃ for 5h. Cool to room temperature, extract with ethyl acetate and saturated brine, retain the organic phase, add anhydrous magnesium sulfate to dry, filter, heat and evaporate to remove excess solvent to obtain a crude product, use column chromatography (pure petroleum ether) to obtain the scintillator material of formula (VI), use dichloromethane and ethanol for recrystallization, and obtain a product mass of 0.36g with a yield of 17%. The specific preparation reaction formula is as follows:

[0061]

[0062] The scintillator material of formula (VI) is characterized by a nuclear magnetic resonance spectrum. Figure 6Shown: 1H NMR (500 MHz, DMSO-d6) δ 7.82 (d, J = 8.0 Hz, 1H), 7.53 (d, J = 7.8 Hz, 1H), 7.45 (t, J = 7.8 Hz, 1H), 7.26 (d, J = 7.5 Hz, 2H), 6.98 (t, J = 7.7 Hz, 2H), 6.87 (t, J = 7.4 Hz, 2H), 6.17 (d, J = 8.3 Hz, 2H), 2.23 (s, 3H).

[0063] Example 7: Performance Comparison of Scintillator Materials

[0064] Photophysical Property Testing

[0065] The scintillator materials of formula (I), formula (II), formula (III), formula (IV), formula (V) and formula (VI) obtained in Examples 1 to 6 were subjected to photophysical property testing, and the results are as Figure 7 and Figure 8 shown.

[0066] Figure 7 In which p-BPSe, p-2BPSe and p-3B correspond to the scintillator materials of formula (I), formula (II) and formula (III) respectively. From Figure 7 a in, under the excitation of 365 nm ultraviolet light, the scintillator materials of formula (I), formula (II) and formula (III) all showed obvious blue-green emission. The luminescence lifetime at this wavelength was tested, and the test results are as Figure 7 shown in b in. The lifetimes of the scintillator materials of formula (I), formula (II) and formula (III) were 217 μs, 60 μs and 94 μs respectively, all of which were lifetimes in the microsecond order and were attributed to phosphorescence. From Figure 7 c in, the phosphorescence quantum efficiencies of the scintillator materials of formula (I), formula (II) and formula (III) were 17%, 10% and 14% respectively.

[0067] Figure 8 In which m-BPSe, m-2BPSe and m-6BPSe correspond to the scintillator materials of formula (IV), formula (V) and formula (VI) respectively. From Figure 8 a in, under the excitation of 365 nm ultraviolet light, the scintillator materials of formula (IV), formula (V) and formula (VI) all showed obvious blue-green emission. The luminescence lifetime at this wavelength was tested, and the test results are as Figure 8 shown in b in. The lifetimes of the scintillator materials of formula (IV), formula (V) and formula (VI) were 1106 μs, 41 μs and 29 μs respectively, all of which were lifetimes in the microsecond order and were attributed to phosphorescence. From Figure 8From c in the above, the phosphorescence quantum efficiencies of the scintillator materials of the formulas (IV), (V), and (VI) are 23%, 10%, and 5% respectively.

[0068] Take 50 mg each of the scintillator materials of the formulas (I), (II), (III), (IV), (V), and (VI), and test their radioluminescence performance under X-rays. The results are as Figure 9 shown. Except for the scintillator material of the formula (IV), the other scintillator materials all exhibit good radioluminescence performance, and among them, the scintillator material of the formula (II) has the best comprehensive properties.

[0069] Comparison of photoluminescence properties

[0070] Compare the photoluminescence properties of the scintillator materials of the formulas (I), (II), (III), (IV), (V), and (VI) obtained in Examples 1 to 6, mainly including the comparison of emission wavelength, efficiency, and lifetime. The results are as Figure 9 shown. Figure 9 In it, p-BPSe, p-2BPSe, p-3B, m-BPSe, m-2BPSe, and m-6BPSe respectively correspond to the scintillator materials of the formulas (I), (II), (III), (IV), (V), and (VI).

[0071] From Figure 9 a in the above, the scintillator materials of the formulas (I), (II), and (III) show almost the same emission peak positions, but there are obvious differences in their lifetimes and emission efficiencies: the scintillator material of the formula (I) is 217 μs, 17%; the scintillator material of the formula (II) is 60 μs, 10%; the scintillator material of the formula (III) is 94 μs, 14%. Under X-ray stimulation, there are obvious intensity differences among the three, which not only illustrates the feasibility of the strategy of regulating the luminescence properties by methyl to control the position of heavy atoms, but also shows the application potential of these materials under X-rays.

[0072] From Figure 9From b in the above, it can be obtained that the scintillator materials of the formulas (IV), (V), and (VI) exhibit almost the same emission peak positions, but there are obvious differences in their lifetimes and luminescence efficiencies: the scintillator material of the formula (IV) is 1106 μs and 23%; the scintillator material of the formula (V) is 41 μs and 10%; the scintillator material of the formula (VI) is 29 μs and 5%. Under X-ray stimulation, there are also obvious intensity differences among the three. The scintillator material of the formula (IV) basically does not have the property of radioluminescence. The radioluminescence properties of the scintillator materials of the formula (V) and the formula (VI) have been gradually improved to a large extent. This not only illustrates the feasibility of the strategy of regulating the luminescence properties by methyl to control the positions of heavy atoms, but also shows the application potential of these materials under X-rays.

[0073] III. X-ray imaging test

[0074] Since the scintillator material of the formula (II) exhibited good comprehensive properties in the above experiments, the X-ray imaging test was carried out using the scintillator material of the formula (II).

[0075] Take 50 mg of the scintillator material of the formula (II) and test its X-ray detection limit. The results are as Figure 10 shown. It can be obtained that the scintillator material of the formula (II) shows good detection limit values, specifically 175 nGy / s.

[0076] Take another 100 mg of the scintillator material of the formula (II) and place it on a glass cover plate. Heat it to 180 °C to completely melt the material, presenting a colorless and transparent liquid state. Then cool it to room temperature to form a homogeneous and transparent glass state. Then use the obtained material for X-ray imaging test and imaging. Figure 11 The transparency of its film formation and its imaging photos are shown. The scintillator material of the formula (II) exhibits good photoluminescence and radioluminescence behaviors. The label of the Santa Claus pattern is well presented, and clear texture patterns are also shown for chip imaging. Then the resolution of the scintillator material of the formula (II) in the glass state was tested. The results are as Figure 12 shown. The resolution of the scintillator material of the formula (II) can reach 27.5 lp / mm, showing great potential in ray imaging.

[0077] The specific embodiments of the present application have been described above, but the protection scope of the present application is not limited thereto. Any person skilled in the art within the technical scope disclosed in the present application can easily think of changes or substitutions, which should all be covered within the protection scope of the present application. Therefore, the protection scope of the present application shall be subject to the protection scope of the claims.

Claims

1. A pure organic X-ray scintillator material, characterized in that: The scintillator material contains a pheneselenazine unit, and the scintillator material is One of them.

2. A method for preparing a pure organic X-ray scintillator material as claimed in claim 1, characterized in that: The preparation method is as follows: S1. Under a nitrogen atmosphere, pheneselenazine, a base, a palladium catalyst and tri-tert-butylphosphine tetrafluoroborate are first dissolved in a toluene solution to form a mixed solution, which is then heated to 90° C. and refluxed for 0.5 h; S2. Under a nitrogen atmosphere, the mixed solution is added into a toluene solution containing halogenated benzene, heated to 90° C. and refluxed for 5 h to obtain a pure organic X-ray scintillator material.

3. The method for preparing a pure organic X-ray scintillator material according to claim 2, characterized in that: The base is potassium tert-butoxide or sodium tert-butoxide.

4. The method for preparing a pure organic X-ray scintillator material according to claim 2, characterized in that: The palladium catalyst is palladium acetate or tris dibenzylideneacetone dipalladium.

5. The method for preparing a pure organic X-ray scintillator material according to claim 2, characterized in that: The halogenated benzene is any one of 1-bromo-4-iodobenzene, 2-bromo-5-iodotoluene, 5-bromo-2-iodotoluene, 1-bromo-3-iodobenzene, 2-bromo-4-iodotoluene or 2-bromo-6-iodotoluene.

6. The method for preparing a pure organic X-ray scintillator material according to claim 2, characterized in that: The structural formula of the phenoselenazine is 7. The method for preparing a pure organic X-ray scintillator material according to claim 2, characterized in that: The molar ratio of the pheneselenazine, the base, the palladium catalyst and tri-tert-butylphosphine tetrafluoroborate is 5:(5-7):(0.2-0.5):(0.2-0.5).

8. The method for preparing a pure organic X-ray scintillator material according to claim 2, characterized in that: The molar ratio of the phenoselenazine to the halogenated benzene is 5:(5-7).

9. Application of the pure organic X-ray scintillator material according to claim 1 in the field of medical X-ray imaging and security inspection.

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