A method for preparing a deuterated compound

Abstract

This invention relates to a method for preparing deuterated compounds, using peroxides (such as D₂O₂) as the key deuterium source, which provides the deuterium atoms required for the reaction. When the peroxide comes into contact with the target compound and under the action of a selected catalyst, the energy of ultraviolet light can excite the reaction system, causing the OD bonds in the peroxide to break and releasing active deuterium atoms. These active deuterium atoms can then exchange with hydrogen atoms in the target compound, completing a hydrogen-deuterium substitution. The advantage of this method is that it can be operated under relatively mild conditions—that is, without the need for extreme temperature or pressure conditions—while still achieving high deuteration rates and yields. This means that this method may be more economically feasible on an industrial scale, reducing energy consumption and the generation of byproducts.

Description

Technical Field

[0001] This invention belongs to the field of organic synthesis technology, and specifically relates to a method for preparing deuterated compounds. Background Technology

[0002] Organic optoelectronic materials (OLED materials) are a rapidly developing new generation of light-emitting materials in recent years, and are widely used in display terminal materials. The rapid decay rate of OLED materials makes their lifespan a major challenge in the development of OLED materials. Studies have shown that deuterated OLED materials, by replacing unstable heterocyclic carbon-hydrogen bonds with hydrogen / deuterium, can improve the stability of the material's spatial structure and significantly extend the device's lifespan. Currently, research on the preparation of deuterated OLED materials is still in its early stages, with two main preparation methods: (1) using commercially available deuterated basic raw materials (such as deuterated benzene, deuterated carbazole, etc.) to synthesize the final target structure through a designed reaction route. This method is limited by the availability of deuterated basic raw materials, and the high cost of deuterated reagents leads to complex synthesis steps, high costs, and low atom utilization; (2) directly replacing the target structure with hydrogen and deuterium. This method has low deuterium source utilization and harsh reaction conditions, which also limits its industrial application. It is difficult to prepare fully deuterated organic optoelectronic materials using the two methods mentioned above, or even if they are successfully prepared, the cost is high and they are difficult to mass-produce. Summary of the Invention

[0003] In order to overcome the shortcomings and deficiencies of the prior art, the purpose of this invention is to provide a method for preparing deuterated compounds.

[0004] A method for preparing a deuterated compound, wherein the chemical reaction process of the deuterated compound is as follows: an aromatic ring compound is dissolved in a solvent and a deuterium source reagent is added, a hydrogen-deuterium exchange reaction is carried out under the action of a catalyst, and the deuterated aromatic ring compound is obtained by purification treatment; The deuterium source reagent contains at least deuterium peroxide; The catalyst is selected from one or more of the following: acid catalysts and metal catalysts.

[0005] Furthermore, the chemical reaction process is as follows: ; The aromatic ring compounds have the structure shown in chemical formula 1; X1-X6, whether identical or different, are selected from N, CH, and C; R1 is selected from: halogen, cyano, nitro, alkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, and hexa-aryl; Or R1 is selected from: six-membered aryl groups substituted with halogen, cyano, nitro, phenyl, alkyl with 1-10 carbon atoms, or alkoxy with 1-10 carbon atoms; Ar1 is selected from: empty, aryl group with 6-20 carbon atoms, and chemical formula 2; When any one of X1-X6 is selected from N, Ar1 is selected from empty; [Chemical Formula 2]; * indicates a connection point; X7, X 7a The elements are independently selected from: O, S, C(R3)(R4), N(R5), and single bonds, and X7 and X 7a Not both are single keys; R3-R4, whether the same or different, are selected from alkyl groups having 1-10 carbon atoms; R5 is selected from: hydrogen, alkyl groups having 1-10 carbon atoms, aryl groups having 6-12 carbon atoms, aryl groups having 6-12 carbon atoms substituted with alkyl groups having 1-10 carbon atoms or alkoxy groups having 1-10 carbon atoms. Furthermore, aryl groups with 6-20 carbon atoms are selected from: fused-ring aryl groups formed by sharing a pair of chemical bonds among 1-3 six-membered aromatic rings; According to the above technical solution, the aryl group with 6-20 carbon atoms is selected from: phenyl and naphthyl; Furthermore, aryl groups with 6-12 carbon atoms are selected from: 1-2 six-membered aromatic rings connected by single bonds, or sharing a pair of chemical bonds to form fused-ring aryl groups; A more preferred embodiment of the above technical solution is that the aryl group with 6-12 carbon atoms is selected from: phenyl, biphenyl, and naphthyl; n = the number of hydrogen atoms in chemical formula 1; m represents: 1, 2, or 3.

[0006] Furthermore, the six-membered aryl group is selected from: phenyl.

[0007] Furthermore, the structure of chemical formula 1 is one of chemical formulas 3 to 6: [Chemical Formula 3]: [Chemical Formula 4]: [Chemical Formula 5]: [Chemical Formula 6]: ; R1 is selected from: hydrogen, phenyl, halogen, C1-C 10 Alkyl, C1-C 10 alkoxy groups; Ar2 is selected from: empty, phenyl, naphthyl; Z is selected from: CH or N; R 2a -R 2c Selected from: hydrogen, halogens, phenyl; Or R 2a -R2c Selected from: by at least one C1-C 10 Alkyl-substituted phenyl groups.

[0008] Furthermore, the structure of chemical formula 3 is selected from any one of the following structures: Chemical formula 3-1: Chemical formula 3-2: Chemical formula 3-3: Chemical formulas 3-4: ; Furthermore, the structure of chemical formula 6 is selected from any one of the following structures: Chemical formula 6-1: Chemical formula 6-2: Chemical formula 6-3: Chemical formula 6-4: Chemical formula 6-5: Chemical formula 6-6: .

[0009] Furthermore, C1-C 10 The alkyl group is selected from: C1-C8 alkyl groups, C1-C6 alkyl groups, and C1-C5 alkyl groups; A more preferred embodiment of the above technical solution is C1-C. 10 The alkyl group is selected from C1-C5 alkyl groups.

[0010] Furthermore, the solvent required for the reaction is selected from one or more of the following: a deuterium peroxide heavy aqueous solution with a concentration of 0.1-50%, heavy water, tetrahydrofuran, dioxane, cyclohexane, benzene, and ethyl acetate; More preferably, according to the above technical solution, the solvent required for the reaction is selected from one or more of the following: a deuterium peroxide heavy aqueous solution with a concentration of 0.1-50%, heavy water, dioxane, and cyclohexane.

[0011] Furthermore, the acid catalyst is a fluoro Lewis acid catalyst or a fluoro Lewis salt catalyst; The metal catalyst is selected from one or more catalysts containing iron, palladium, platinum, titanium, cesium, and aluminum.

[0012] Furthermore, the acid catalyst is selected from one or more of the following: trifluoromethanesulfonic acid, perfluoroethylsulfonic acid, perfluoropropylsulfonic acid, perfluorobutylsulfonic acid, trifluoroacetic acid, perfluoropropionic acid, and perfluorobutyric acid; The metal catalyst is selected from one or more of the following: ferrous sulfate heptahydrate, ferrous sulfate, ferrous chloride, ferrous carbonate, ferrous sulfate, titanium dioxide, cesium carbonate, palladium / carbon, platinum / carbon, tetra-triphenylphosphine palladium, dichlorobis(1,1'-bis(diphenylphosphine)ferrocene)palladium, tris(dibenzylacetone)palladium, palladium acetate, and palladium / alumina.

[0013] Furthermore, the reaction process also includes a phase transfer catalyst.

[0014] Furthermore, the phase transfer catalyst is selected from any one or a combination of several of the following: crown ether compounds, quaternary ammonium salt compounds, quaternary ammonium base compounds, and quaternary phosphonium salt compounds; More preferably, according to the above technical solution, the phase transfer catalyst is selected from any one or a combination of several of the following: crown ether compounds, quaternary ammonium salt compounds, and quaternary ammonium base compounds; Furthermore, the crown ether compounds are selected from: 18-crown-6, 15-crown-5, dibenzo-18-crown-6, and dicyclohexano-18-crown-6; Furthermore, the quaternary ammonium salt compounds are selected from: tetrabutylammonium bromide, tetrabutylammonium chloride, benzyltriethylammonium chloride, dodecyltrimethylammonium chloride, and hexadecyltrimethylammonium bromide; Furthermore, the quaternary ammonium base compounds are selected from: tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, dodecyltrimethylammonium hydroxide, and hexadecyltrimethylammonium hydroxide.

[0015] Furthermore, the hydrogen-deuterium exchange reaction is carried out in a UV light environment.

[0016] Furthermore, the wavelength of UV light is selected from light sources ranging from 10nm to 400nm; A more preferred embodiment of the above technical solution is that the wavelength of the UV light source is selected from 300nm to 400nm.

[0017] Furthermore, the deuterium source reagent also contains deuterium water, deuterated methanol, deuterated ethanol, deuterated isopropanol, deuterated methane, deuterated dimethyl sulfoxide, and deuterated benzene.

[0018] Furthermore, the weight ratio of chemical formula 1 to deuterium source reagent is 1:1-100.

[0019] Furthermore, the molar ratio of chemical formula 1 to catalyst is 1:1‰-2.0; A more preferred embodiment of the above technical solution is that the molar ratio of chemical formula 1 to acid catalyst is 1:1-2.0; A more preferred embodiment of the above technical solution is that the molar ratio of chemical formula 1 to metal catalyst is 1:1‰-5%.

[0020] Furthermore, the molar ratio of chemical formula 1 to phase transfer catalyst is 1:0.1-1; A more preferred embodiment of the above technical solution is that the molar ratio of chemical formula 1 to phase transfer catalyst is 1:0.1-0.5.

[0021] The present invention has the following advantages and effects compared with the prior art: 1) Achieving efficient deuteration under mild conditions: Traditional deuteration methods typically rely on deuterium sources such as deuterated water (D₂O) or deuterated benzene (C₆D₆), which often require high temperatures, high pressures, or large quantities of deuterium to ensure an effective deuteration reaction. This invention utilizes peroxides as a deuterium source, enabling efficient deuteration under relatively mild conditions. This method reduces the need for extreme conditions, minimizes potential safety risks, and simplifies the experimental setup and operational procedures.

[0022] 2) Lowering the activation energy improves selectivity and deuteration rate: Peroxides, acting as deuterium sources, can release ·OD⁻ at relatively low energies. Compared to deuterated water (D₂O), ·OD⁻ in peroxides is more easily excited, especially under ultraviolet (UV) light irradiation, which significantly reduces the required activation energy. Lower activation energy translates to faster reaction rates and higher reaction selectivity, and also increases the deuteration rate in the target compound. In this reaction system, UV light provides the substrate with the energy required to transition from the ground state to the excited state, making the substrate molecule more receptive to deuterium atoms; furthermore, UV light accelerates the decomposition of peroxides, encouraging more ·OD⁻ to participate in the reaction. These two effects work together to greatly enhance the overall reaction rate, achieving rapid and efficient deuteration. UV light, as a clean and easily controlled energy source, demonstrates unique advantages in this process, promoting efficient and selective deuteration reactions.

[0023] 3) Ultraviolet light enhances catalytic activity and lowers activation energy: Ultraviolet (UV) irradiation further enhances the performance of transition metal catalysts. The energy of UV light is sufficient to excite electrons in the catalyst to transition from the ground state to higher energy levels, thereby altering the oxidation state or coordination environment of the metal center. For the transition metal catalysts involved in this invention, the activation effect of UV light makes it easier for the catalyst to accept and release substrate molecules, thus promoting the reaction. Attached Figure Description

[0024] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0025] Figure 1 This is the mass spectrum of deuterated carbazole. Detailed Implementation

[0026] The embodiments of the present invention will be clearly and completely described below with reference to the examples. These described embodiments are merely some, not all, of the embodiments of the present invention. The following description of at least one exemplary embodiment is merely illustrative and is in no way intended to limit the present invention or its application or use. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without inventive effort are within the scope of protection of the present invention.

[0027] Unless otherwise specified, all reagents and instruments used in this invention are commercially available products. For process parameters not specifically stated, conventional techniques can be used as a reference.

[0028] Example 1 This embodiment provides a method for synthesizing deuterated benzene:

[0029] In a round-bottom flask, 500 ml of a 25% deuterium peroxide aqueous solution and 10 g of benzene were added. Nitrogen gas was introduced to replace the air, and 0.15 g of palladium on carbon was added. The UV spectrometer was turned on (365 nm), and the mixture was stirred and heated to 85 °C overnight. After reacting overnight, the mixture was cooled to room temperature. The deuterium peroxide was quenched with manganese dioxide, and the mixture was allowed to stand and separate into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 9.04 g of deuterated benzene, with a yield of 83.92%. Mass spectrometry: 84.

[0030] Example 2 This embodiment provides a method for synthesizing deuterated carbazole:

[0031] In a round-bottom flask, 700 ml of a 25% deuterium peroxide aqueous solution and 10 g of carbazole were added. Nitrogen gas was bubbled through to replace the air. 0.1 g of palladium on carbon and 7.16 g of titanium dioxide were added. The UV spectrometer was turned on (365 nm), and the mixture was stirred and heated to 90 °C overnight. After reacting overnight, the mixture was cooled to room temperature. The deuterium peroxide was quenched with manganese dioxide, and the mixture was allowed to stand and separate into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 9.27 g of deuterated carbazole, with a yield of 88.44%. Mass spectrometry: 175.

[0032] Example 3 This embodiment provides a method for synthesizing deuterated bromobenzene:

[0033] In a round-bottom flask, 450 ml of a 25% deuterium peroxide aqueous solution and 10 g of bromobenzene were added. Nitrogen gas was bubbled through to replace the air, and 0.07 g of palladium on carbon was added. The UV spectrometer was turned on (365 nm), and the mixture was stirred and heated to 90 °C overnight. After reacting overnight, the mixture was cooled to room temperature. The deuterium peroxide was quenched with manganese dioxide, and the mixture was allowed to stand and separate into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 8.69 g of deuterated bromobenzene, with a yield of 84.20%. Mass spectrometry: 160.

[0034] Example 4 This embodiment provides a method for synthesizing deuterated 9,9-dimethylfluorene:

[0035] In a round-bottom flask, 700 ml of a 25% deuterium peroxide aqueous solution, 10 g of 9,9-dimethylfluorene, and 2.72 g of 18-crown ether-6 were added. Nitrogen gas was bubbled through to replace the air, and 0.06 g of palladium on carbon was added. The mixture was then heated to 85°C with stirring overnight. After cooling to room temperature, the mixture was quenched with manganese dioxide, allowed to stand, and separated into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 9.74 g of deuterated 9,9-dimethylfluorene, with a yield of 93.53%. Mass spectrometry: 202.

[0036] Example 5 This embodiment provides a method for synthesizing deuterated 2-bromo-4,6-diphenyl-1,3,5-triazine: The reaction process is as follows:

[0037] In a round-bottom flask, 700 ml of a 25% deuterium peroxide aqueous solution, 10 g of 2-bromo-4,6-diphenyl-1,3,5-triazine, and 1.69 g of 18-crown ether-6 were added. Nitrogen gas was introduced to replace the air, and 0.06 g of platinum carbon was added. The mixture was then heated to 85°C with stirring overnight. After cooling to room temperature, the mixture was quenched with manganese dioxide, allowed to stand, and separated into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 9.46 g of deuterated 2-bromo-4,6-diphenyl-1,3,5-triazine, with a yield of 91.65%. Mass spectrometry: 321.

[0038] Example 6 This embodiment provides a method for synthesizing deuterated 2,8-di-tert-butyldibenzo[b,d]furan:

[0039] In a round-bottom flask, 700 ml of a 25% deuterium peroxide aqueous solution and 10 g of 2,8-di-tert-butyldibenzo[b,d]furan were added. Nitrogen gas was introduced to replace the air. 0.07 g of palladium on carbon and 4.29 g of titanium dioxide were added. The UV spectrometer was turned on (365 nm), and the mixture was stirred and heated to 90 °C overnight. After reacting overnight, the mixture was cooled to room temperature. The deuterium peroxide was quenched with manganese dioxide, and the mixture was allowed to stand and separate into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 8.97 g of deuterated 2,8-di-tert-butyldibenzo[b,d]furan, with a yield of 87.80%. Mass spectrometry: 286. Example

[0040] This embodiment provides a method for synthesizing deuterated 10-phenyl-phenoxazine:

[0041] In a round-bottom flask, 1000 ml of a 25% deuterium peroxide aqueous solution and 10 g of 10-phenyl-phenoxazine were added. Nitrogen gas was bubbled through to replace the air. 0.08 g of palladium acetate and 1.76 g of benzyltriethylammonium chloride were added. The UV spectrometer was turned on (365 nm), and the mixture was stirred and heated to 90 °C overnight. After reacting overnight, the mixture was cooled to room temperature. The deuterium peroxide was quenched with manganese dioxide, and the mixture was allowed to stand and separate into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 9.41 g of deuterated 10-phenyl-phenoxazine, with a yield of 89.58%. Mass spectrometry: 272.

[0042] Example 8 This embodiment provides a method for synthesizing deuterated bromobenzene:

[0043] In a round-bottom flask, 450 ml of a 25% deuterium peroxide aqueous solution and 10 g of bromobenzene were added. Nitrogen gas was bubbled through to replace the air, and 23.90 g of trifluoromethanesulfonic acid was added. The UV spectrometer was turned on (365 nm), and the mixture was stirred and heated to 90 °C overnight. After reacting overnight, the mixture was cooled to room temperature. The deuterium peroxide was quenched with manganese dioxide, and the mixture was allowed to stand and separate into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 8.67 g of deuterated bromobenzene, with a yield of 84.01%. Mass spectrometry: 160.

[0044] Example 9 This embodiment provides a method for synthesizing deuterated benzene:

[0045] In a round-bottom flask, 500 ml of a 25% deuterium peroxide aqueous solution and 10 g of benzene were added. Nitrogen gas was introduced to replace the air, and 0.15 g of palladium on carbon was added. The mixture was stirred and heated to 85°C overnight. After cooling to room temperature, the deuterium peroxide was quenched with manganese dioxide, and the mixture was allowed to stand to separate into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 5.35 g of deuterated benzene, with a yield of 49.66%. Mass spectrometry: 84.

[0046] Example 10 This embodiment provides a method for synthesizing deuterated anthracene:

[0047] In a round-bottom flask, 600 ml of a 25% deuterium peroxide aqueous solution and 10 g of anthracene were added. Nitrogen gas was bubbled through to replace the air, and 3.12 g of ferrous sulfate heptahydrate was added. The mixture was then heated to 85 °C with stirring, and the pH was maintained between 3 and 4 using 0.1 mol / L HCl during heating. After reacting overnight, the mixture was cooled to room temperature. The deuterium peroxide was quenched with manganese dioxide, and the mixture was allowed to stand and separate into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 9.29 g of deuterated anthracene, with a yield of 87.94%. Mass spectrometry: 188.

[0048] Example 11 This embodiment provides a method for synthesizing deuterated 9,9-dimethylfluorene:

[0049] In a round-bottom flask, 700 ml of a 25% deuterium peroxide aqueous solution and 10 g of 9,9-dimethylfluorene were added. Nitrogen gas was bubbled through to replace the air, and 2.86 g of ferrous sulfate heptahydrate was added. The mixture was then heated to 85°C with stirring, and the pH was maintained between 3 and 4 using 0.1 mol / L HCl during heating. After reacting overnight, the mixture was cooled to room temperature. The deuterium peroxide was quenched with manganese dioxide, and the mixture was allowed to stand until separation. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was separated by column chromatography to obtain 9.60 g of deuterated 9,9-dimethylfluorene, with a yield of 92.18%. Mass spectrometry: 202.

[0050] Comparative Example 1:

[0051] In a round-bottom flask, 500 ml of deuterated water and 10 g of benzene were added. Nitrogen gas was introduced to replace the air, and 0.15 g of palladium on carbon was added. The mixture was heated to 85°C with UV light (365 nm) and stirred overnight. After cooling to room temperature, the mixture was quenched with manganese dioxide to remove deuterium peroxide. The layers were allowed to separate, and the organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was then separated by column chromatography to obtain 6.24 g of deuterated benzene, with a yield of 57.92%.

[0052] Comparative Example 2:

[0053] In a round-bottom flask, 700 ml of a 25% deuterium peroxide aqueous solution and 10 g of 9,9-dimethylfluorene were added. Nitrogen gas was bubbled through to replace the air, and 0.6 g of tetraphenylphosphine palladium was added. The mixture was then heated to 85°C with stirring overnight. After cooling to room temperature, the mixture was quenched with manganese dioxide, allowed to stand, and separated into layers. The organic layer was extracted with ethyl acetate. Residual water was removed with magnesium sulfate, and the mixture was distilled under reduced pressure. The mixture was then separated by column chromatography to obtain 7.59 g of deuterated 9,9-dimethylfluorene, with a yield of 72.88%.

[0054] Determination of deuteration rate (refer to CN118955273A): Experimental Example Experimental Example 1 Experimental Example 2 Experimental Example 3 Experiment Example 4 Experimental Example 5 Experimental Example 6 Experimental Example 7 Deuteration rate 98.7% 99.0% 98.8% 99.6% 99.8% 99.2% 99.9% Experimental Example Experimental Example 8 Experimental Example 9 Experimental Example 10 Experimental Example 11 Comparative Example 1 Comparative Example 2 Deuteration rate 98.0% 94.1% 99.4% 99.6% 72.4% 83.8% By comparing the comparative examples with the actual examples, the synthesis efficiency of deuteration was significantly improved under ultraviolet light irradiation and the addition of an auxiliary catalyst. The purity and deuteration rate of the product were also greatly improved. In addition, the method of using peroxide as a deuterium source can greatly improve the deuteration rate compared with the traditional deuterium source.

Claims

1. A method for preparing a deuterated compound, characterized in that, The chemical reaction process of the deuterated compound is as follows: after the aromatic ring compound is dissolved in a solvent, a deuterium source reagent is added, and a hydrogen-deuterium exchange reaction occurs under the action of a catalyst. The deuterated aromatic ring compound is obtained by purification treatment. The deuterium source reagent contains at least deuterium peroxide; The catalyst is selected from one or more of the following: acid catalysts and metal catalysts.

2. The method for preparing a deuterated compound according to claim 1, characterized in that, The chemical reaction process is as follows: ; The aromatic ring-containing compound has the structure shown in Chemical Formula 1; X1-X6, whether identical or different, are selected from N, CH, and C; R1 is selected from: halogen, cyano, nitro, alkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, and hexa-aryl; Or R1 is selected from: six-membered aryl groups substituted with halogen, cyano, nitro, phenyl, alkyl with 1-10 carbon atoms, or alkoxy with 1-10 carbon atoms; Ar1 is selected from: empty, aryl group with 6-20 carbon atoms, and chemical formula 2; [Chemical Formula 2]; * indicates a connection point; X7, X 7a The elements are independently selected from: O, S, C(R3)(R4), N(R5), and single bonds, and X7 and X 7a Not both are single keys; R3-R4, whether the same or different, are selected from alkyl groups having 1-10 carbon atoms; R5 is selected from: hydrogen, alkyl groups having 1-10 carbon atoms, aryl groups having 6-12 carbon atoms, aryl groups having 6-12 carbon atoms substituted with alkyl groups having 1-10 carbon atoms or alkoxy groups having 1-10 carbon atoms. n = the number of hydrogen atoms in chemical formula 1; m represents: 1, 2, or 3.

3. The method for preparing a deuterated compound according to claim 2, characterized in that, The structure of chemical formula 1 is one of chemical formulas 3 to 6: [Chemical Formula 3]: [Chemical Formula 4]: [Chemical Formula 5]: [Chemical Formula 6]: ; R1 is selected from: hydrogen, phenyl, halogen, C1-C 10 Alkyl, C1-C 10 alkoxy groups; Ar2 is selected from: empty, phenyl, naphthyl; Z is selected from: CH or N; R 2a -R 2c Selected from: hydrogen, halogens, phenyl; Or R 2a -R 2c Selected from: by at least one C1-C 10 Alkyl, C1-C 10 alkoxy groups, C1-C 10 alkylthio-substituted phenyl groups.

4. The method for preparing a deuterated compound according to claim 1, characterized in that, The acid catalyst is a fluoro Lewis acid catalyst or a fluoro Lewis salt catalyst. The metal catalyst is selected from one or more catalysts containing iron, palladium, platinum, titanium, cesium, and aluminum. Chemical Formula 1: The molar ratio of the catalyst is 1:1‰-2.

0.

5. The method for preparing a deuterated compound according to claim 4, characterized in that, The acid catalyst is selected from one or more of the following: trifluoromethanesulfonic acid, perfluoroethylsulfonic acid, perfluoropropylsulfonic acid, perfluorobutylsulfonic acid, trifluoroacetic acid, perfluoropropionic acid, and perfluorobutyric acid. The metal catalyst is selected from one or more of the following: ferrous sulfate heptahydrate, ferrous sulfate, ferrous chloride, ferrous carbonate, ferrous sulfate, titanium dioxide, cesium carbonate, palladium / carbon, platinum / carbon, tetra-triphenylphosphine palladium, dichlorobis(1,1'-bis(diphenylphosphine)ferrocene)palladium, tris(dibenzylacetone)palladium, palladium acetate, and palladium / alumina.

6. The method for preparing a deuterated compound according to claim 1, characterized in that, The reaction process also includes a phase transfer catalyst; Chemical Formula 1: The molar ratio of the phase transfer catalyst is 1:0.1-1.

7. The method for preparing a deuterated compound according to claim 6, characterized in that, The phase transfer catalyst is selected from any one or a combination of several of crown ether compounds, quaternary ammonium salt compounds, quaternary ammonium base compounds, and quaternary phosphonium salt compounds.

8. The method for preparing a deuterated compound according to claim 1, characterized in that, The hydrogen-deuterium exchange reaction is carried out under UV light.

9. The method for preparing a deuterated compound according to claim 1, characterized in that, The deuterium source reagent also contains deuterium water, deuterated methanol, deuterated ethanol, deuterated isopropanol, deuterated methane, deuterated dimethyl sulfoxide, and deuterated benzene.

10. The method for preparing a deuterated compound according to claim 3, characterized in that, The structure of chemical formula 3 is selected from chemical formulas 3-1 to 3-4: Chemical formula 3-1: Chemical formula 3-2: Chemical formula 3-3: Chemical formulas 3-4: ; The structure of chemical formula 6 is selected from chemical formulas 6-1 to 6-6: Chemical formula 6-1: Chemical formula 6-2: Chemical formula 6-3: Chemical formula 6-4: Chemical formula 6-5: Chemical formula 6-6: .

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