Synthesis method of deuterated carbazole compounds
By using acid and amine catalysts for deuteration reaction at low temperature, the problems of multiple steps and high cost in the synthesis of deuterated carbazole compounds in the prior art have been solved, and the synthesis of deuterated carbazole compounds with high yield and high quality has been achieved.
Patent Information
- Application Number
- CN202610512210.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2026-04-17
- Publication Date
- 2026-07-07
AI Technical Summary
Existing methods for synthesizing deuterated carbazole compounds require multiple steps and are costly, using expensive catalysts and exhibiting poor functional group compatibility, resulting in low product purity and yield.
The deuteration reaction is carried out at low temperature using acid and catalyst, with amine compounds used as catalysts to avoid autocoupling side reactions and improve yield and product quality.
This method enables the synthesis of deuterated carbazole compounds with high yield and high quality, reduces synthesis costs, and simplifies process steps.
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Figure CN122344202A_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the field of organic synthesis, and specifically relates to a method for synthesizing deuterated carbazole compounds. Background Technology
[0002] Deuterated compounds are new compounds obtained by replacing one or more hydrogen atoms in the carbon-hydrogen bonds of a compound molecule with deuterium atoms. They are an important class of high-value-added chemicals, widely used as solvents in the field of nuclear magnetic resonance (NMR) and a hot topic in new drug development in recent years. Deuterated compounds show promising applications in biological metabolism analysis, NMR, optoelectronic materials, scientific research and testing, intermediate labeling, drug development, and pollution source tracking.
[0003] Deuterated compounds, with their unique kinetic isotope effect, have become a core material strategy for overcoming the lifespan bottleneck of next-generation PHOLEDs (phosphorescent organic light-emitting diodes). By "reinforcing" the microscopic framework of organic molecules, they fundamentally solve the material degradation problem caused by the long exciton lifetime of PHOLEDs. This is not only an effective means to solve the lifespan problem of next-generation display technologies, but also a necessary process for achieving high-reliability mass production of high-end OLED panels.
[0004] The structure of deuterated carbazole compounds is as follows: , Where R 12 Selected from H, substituted by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any one of the heteroaryl groups; Where R 22 R 32 R 42 R 52 R 62 R 72 R 82 R 92 The same or different, selected from those replaced by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any one of the heteroaryl groups; or R22 R 32 R 42 R 52 R 62 R 72 R 82 R 92 Adjacent components are replaced by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any of the heteroaryl groups.
[0005] Carbazole compounds, as common materials in organic chemistry, have been widely used in medicine, pesticides, dyes, optoelectronic materials, and synthetic resins.
[0006] In pharmaceuticals, carbazole and the nonsteroidal antibacterial drug carbofen are used as antibacterial agents; roserine, pyrrolocarbazole derivatives, and carbazole amide compounds have inhibitory effects on tumor cells; the new carbazole drug midotulin can be used to treat FLT3 mutation-positive acute myeloid leukemia (AML). In optoelectronic materials, because the carbazole backbone unit contains a large n-electron conjugated system, it has a strong electron transfer capability and a rigid fused-ring backbone structure. Therefore, carbazole derivatives have been widely used to construct fluorescent molecular probes, sensors, light-emitting diodes, and organic light-emitting electronic devices, and are widely used in OLEDs to construct bipolar blue light materials.
[0007] Correspondingly, deuterated carbazole compounds are gradually replacing carbazole compounds because the deuterium atoms replace hydrogen atoms, which significantly alters the physical, chemical, and biological properties of the original molecules.
[0008] Currently, the synthesis of deuterated carbazole compounds requires multiple steps to obtain the final product. There are various methods for synthesizing deuterated carbazole compounds: The first synthetic method involves synthesizing a deuterated intermediate, followed by dehydrogenation cyclization, coupling, and other reactions to obtain deuterated carbazole. Then, other reaction methods are used to add groups to deuterated aniline to obtain deuterated carbazole compounds.
[0009] The second synthetic method was developed in 2015 by Chiharu Suzuki et al., who used deuterated o-aminobiphenyl as a raw material and employed an iridium catalyst for NC coupling to obtain deuterated carbazole.
[0010] The third synthesis method was developed in 2016 by WenLixian et al., who used Pd(OAc) and Cu(0Ac) as catalysts and deuterated diphenylamine as a raw material to synthesize deuterated carbazole.
[0011] However, all three methods require multiple steps for synthesis, and deuteration does not occur in the final step, which greatly increases the cost of synthesizing deuterated carbazole.
[0012] To simplify the synthesis process, existing techniques involve directly preparing deuterated carbazoles from carbazole compounds via hydrogen-deuterium exchange, thus reducing the number of steps in the synthesis of deuterated carbazole compounds. However, this method requires a large amount of expensive Pt catalyst and reacts at a high temperature of around 200°C, which significantly increases the synthesis cost and is not conducive to industrial production. Furthermore, this method suffers from poor functional group compatibility and a narrow range of substrates that can be prepared.
[0013] The method using acid catalysis and deuterated benzenes as deuteration raw materials has higher group compatibility, but carbazole compounds undergo self-coupling side reactions during deuteration, resulting in lower product purity and yield. Summary of the Invention
[0014] To address the shortcomings of existing technologies, this invention provides a method for synthesizing deuterated carbazole compounds. This method, by adding a catalytic amount of catalyst followed by deuteration, avoids the generation of autocoupling side reactions, achieving higher yields and product quality.
[0015] To achieve the purpose of the invention, the present invention adopts the following technical solution: A method for synthesizing deuterated carbazole compounds includes reacting a carbazole starting material with a deuterating reagent in the presence of an acid and a catalyst, wherein the general reaction formula is: R1 is selected from H, and C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any one of the heteroaryl groups; R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and are selected from H, C1-C. 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any one of the heteroaryl groups; Or, R2, R3, R4, R5, R6, R7, R8, and R9 are adjacent and form a group that is not substituted or is C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any of the heteroaryl groups. Preferably, it is a benzene ring, naphthalene ring, biphenyl ring, or carbazole ring that is unsubstituted or substituted with a halogen atom; Where R 12 Selected from H, substituted by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any one of the heteroaryl groups; Where R 22 R 32 R 42 R 52 R 62 R 72 R 82 R 92 The same or different, selected from those replaced by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any one of the heteroaryl groups; Where R 22 R 32 R 42 R 52 R 62 R 72 R 82 R 92 Adjacent components are replaced by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any of the heteroaryl groups.
[0016] Preferably, R1 is selected from H, an unsubstituted or halogen-substituted benzene ring, biphenyl, naphthalene ring, or carbazole ring; R2, R3, R4, R5, R6, R7, R8, and R9 are selected from H, Br, F, and Cl, an unsubstituted or halogen-substituted benzene ring, naphthalene ring, biphenyl, or carbazole ring; or R2, R3, R4, R5, R6, R7, R8, and R9 are selected from an unsubstituted or halogen-substituted benzene ring, naphthalene ring, biphenyl, or carbazole ring; wherein R 12 Selected from H, benzene rings substituted with D or halogen atoms, biphenyl rings, naphthalene rings, and carbazole rings; R 22 R 32 R 42 R 52 R 62 R 72 R 82 R 92 Selected from benzene rings, naphthalene rings, biphenyl rings, carbazole rings that are D, F, Br, Cl, or substituted with D or halogen atoms; or R 22 R 32 R 42 R 52 R 62 R 72 R 82 R 92 Selected from benzene rings, naphthalene rings, biphenyl rings, and carbazole rings that are substituted with D or substituted with halogen atoms.
[0017] Preferably, the deuterated reagent is a deuterated benzene compound, selected from deuterated benzene, deuterated toluene, and deuterated dibenzene. Toluene, deuterated trimethylbenzene, or deuterated chlorobenzene.
[0018] Preferably, the catalyst is an amine compound selected from EDTA, propylenediamine, 1,2-diaminocyclohexane, or hydroxylamine hydrochloride.
[0019] Preferably, the molar ratio of the catalyst to the carbazole raw material is 0.005:1-0.1:1, more preferably 0.01:1-0.05:1.
[0020] Preferably, the acid is selected from sulfuric acid, trifluoromethanesulfonic acid, or methanesulfonic acid, with trifluoromethanesulfonic acid being the most preferred.
[0021] Preferably, the carbazole raw material is selected from the following compounds: , , , , , R1 is selected from H, and C1-C 12 C6-C40 aryl groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups; or aryl groups substituted with C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any one of the heteroaryl groups; R2 is selected from H, and C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any of the heteroaryl groups.
[0022] Preferably, the deuterated carbazole compound is selected from the following compounds: , , , , , Where R 12 Selected from H, substituted by D, or substituted by C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any one of the heteroaryl groups; Where R 22 Selected from those replaced by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any of the heteroaryl groups.
[0023] This invention relates to a method for synthesizing deuterated carbazole compounds, which avoids the need for large amounts of expensive Pt catalysts and enables the reaction to be carried out at low temperatures. By adding amine catalysts and then performing deuteration, the generation of autogenous side reactions is avoided, resulting in higher yields and product quality. Attached Figure Description
[0024] Figure 1 This is the HPLC chromatogram of Example 1.
[0025] Figure 2 This is the HPLC chromatogram of Example 2.
[0026] Figure 3 This is the HPLC chromatogram of Comparative Example 1.
[0027] Figure 4 This is the HNMR chromatogram of Example 1.
[0028] Figure 5 This is the HNMR chromatogram of Example 2.
[0029] Figure 6 This is the HNMR chromatogram of Example 3.
[0030] Figure 7 This is the HNMR chromatogram of Example 4.
[0031] Figure 8 This is the HNMR chromatogram of Example 5. Detailed Implementation
[0032] The following detailed description of the present invention, through several specific examples, further illustrates the above-described contents of the invention. However, this should not be construed as limiting the scope of the invention to the following specific embodiments. All techniques experimented with based on the above-described contents of the present invention fall within the scope of the present invention. Example 1
[0033] 5 g of 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindole[2,3-C]carbazole, 339 g of deuterated benzene, 2.75 g (1.5 eq) of trifluoromethanesulfonic acid, and 0.11 g (0.03 eq) of ethylenediaminetetraacetic acid were added to a reaction flask and reacted at 50-55 °C for 48 hours. The main content of the reaction solution was 97.52% as determined by liquid chromatography. Column chromatography on tetrahydrofuran / petroleum ether yielded 4.75 g of pure deuterated 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindole[2,3-C]carbazole, with a yield of 95%. The deuteration rate was 98.3% as determined by ¹H NMR.
[0034] In Example 1, the deuterated benzene can be replaced with deuterated toluene, deuterated xylene, deuterated trimethylbenzene, or deuterated chlorobenzene, and the reaction effect is the same. Example 2
[0035] 5 g of 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindole[2,3-C]carbazole, 339 g of deuterated benzene, 2.75 g (1.5 eq) of trifluoromethanesulfonic acid, and 0.026 g (0.03 eq) of hydroxylamine hydrochloride were added to a reaction flask and reacted at 75-78 °C for 48 hours. The main content of the reaction solution was 97.46% as determined by liquid chromatography. Column chromatography on tetrahydrofuran / petroleum ether yielded 4.77 g of pure deuterated 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindole[2,3-C]carbazole, with a yield of 95.4%. The deuteration rate was 98.1% as determined by ¹H NMR.
[0036] In Example 2, hydroxylamine hydrochloride can also be replaced by EDTA, propylenediamine, or 1,2-diaminocyclohexane, with the same reaction effect. Example 3
[0037] 5 g of 4-bromocarbazole, 225.6 g of deuterated benzene, 4.57 g (1.5 eq) of trifluoromethanesulfonic acid, and 0.18 g (0.03 eq) of ethylenediaminetetraacetic acid were added to a reaction flask and reacted at 75-78 °C for 48 hours. Column chromatography with dichloromethane / petroleum ether yielded 4.80 g of pure deuterated 4-bromocarbazole, with a yield of 96%. ¹H NMR analysis showed a deuteration rate of 96.3%.
[0038] In Example 3, trifluoromethanesulfonic acid can be replaced by sulfuric acid or methanesulfonic acid. Example 4
[0039] 5 g of 3,9'-bicarbazole, 334 g of deuterated benzene, 3.39 g (1.5 eq) of trifluoromethanesulfonic acid, and 0.13 g (0.03 eq) of ethylenediaminetetraacetic acid were added to a reaction flask and reacted at 75-78 °C for 48 hours. The deuterated 3,9'-bicarbazole was obtained by column chromatography on tetrahydrofuran / petroleum ether with a yield of 96% and a deuteration rate of 98.1% as determined by HNMR. Example 5
[0040] 5 g of 5-([1,1'-biphenyl]-3-yl)-5,8-dihydroindole[2,3-C]carbazole, 339 g of deuterated benzene, 2.75 g (1.5 eq) of trifluoromethanesulfonic acid, and 0.026 g (0.03 eq) of hydroxylamine hydrochloride were added to a reaction flask and reacted at 75-78 °C for 48 hours. Column chromatography on tetrahydrofuran / petroleum ether yielded 4.69 g of pure deuterated 5-([1,1'-biphenyl]-3-yl)-5,8-dihydroindole[2,3-C]carbazole, with a yield of 93.8% and a deuteration rate of 82% as determined by HNMR.
[0041] Comparative Example 1 5 g of 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindole[2,3-C]carbazole, 339 g of deuterated benzene, and 2.75 g (1.5 eq) of trifluoromethanesulfonic acid were added to a reaction flask and reacted at 50-55 °C for 48 hours. The main content of the reaction solution was 89.89% as determined by liquid chromatography. Column chromatography on tetrahydrofuran / petroleum ether yielded 3.9 g of pure deuterated 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindole[2,3-C]carbazole, with a yield of 78%. The deuteration rate was 98.3% as determined by ¹H NMR.
[0042] Comparative Example 2 5 g of 4-bromocarbazole, 225.6 g of deuterated benzene, and 4.57 g (1.5 eq) of trifluoromethanesulfonic acid were added to a reaction flask and reacted at 75-78 °C for 48 hours. Column chromatography with tetrahydrofuran / petroleum ether yielded 3.95 g of pure deuterated 4-bromocarbazole, with a yield of 79%. ¹H NMR analysis showed a deuteration rate of 96.13%.
[0043] Comparative Example 3 5 g of 3,9'-bicarbazole, 334 g of deuterated benzene, and 3.39 g (1.5 eq) of trifluoromethanesulfonic acid were added to a reaction flask and reacted at 75-78 °C for 48 hours. The deuterated 3,9'-bicarbazole was obtained by column chromatography on tetrahydrofuran / petroleum ether with a yield of 84% and a deuteration rate of 98.3% as determined by HNMR.
[0044] Comparative Example 4: 5 g of 5-([1,1'-biphenyl]-3-yl)-5,8-dihydroindole[2,3-C]carbazole, 339 g of deuterated benzene, and 2.75 g (1.5 eq) of trifluoromethanesulfonic acid were added to a reaction flask and reacted at 75-78 °C for 48 hours. Column chromatography on tetrahydrofuran / petroleum ether yielded 4.11 g of pure deuterated 5-([1,1'-biphenyl]-3-yl)-5,8-dihydroindole[2,3-C]carbazole, with a yield of 82.2% and a deuteration rate of 81% as determined by HNMR.
Claims
1. A method for synthesizing deuterated carbazole compounds, characterized in that... This includes the reaction of carbazole-based starting materials and deuterated reagents in the presence of acid and a catalyst, with the general reaction formula as follows: R1 is selected from H, and C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any one of the heteroaryl groups; R2, R3, R4, R5, R6, R7, R8, and R9 may be the same or different, and are selected from H, C1-C. 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any one of the heteroaryl groups; Or, R2, R3, R4, R5, R6, R7, R8, and R9 are adjacent and form a group that is not substituted or is C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any of the heteroaryl groups. Preferably, it is a benzene ring, naphthalene ring, biphenyl ring, or carbazole ring that is unsubstituted or substituted with a halogen atom; Where R 12 Selected from H, substituted by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any one of the heteroaryl groups; Where R 22 R 32 R 42 R 52 R 62 R 72 R 82 R 92 The same or different, selected from those replaced by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any one of the heteroaryl groups; Where R 22 R 32 R 42 R 52 R 62 R 72 R 82 R 92 Adjacent components are replaced by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any of the heteroaryl groups.
2. The method for synthesizing a deuterated carbazole compound according to claim 1, characterized in that... Wherein R1 is selected from H, unsubstituted or halogen-substituted benzene rings, biphenyl rings, naphthalene rings, and carbazole rings; R2, R3, R4, R5, R6, R7, R8, and R9 are selected from H, Br, F, and Cl, unsubstituted or halogen-substituted benzene rings, naphthalene rings, biphenyl rings, and carbazole rings; or R2, R3, R4, R5, R6, R7, R8, and R9 are selected from unsubstituted or halogen-substituted benzene rings, naphthalene rings, biphenyl rings, and carbazole rings; where R 12 Selected from H, benzene rings substituted with D or halogen atoms, biphenyl rings, naphthalene rings, and carbazole rings; R 22 R 32 R 42 R 52 R 62 R 72 R 82 R 92 Selected from benzene rings, naphthalene rings, biphenyl rings, carbazole rings that are D, F, Br, Cl, or substituted with D or halogen atoms; or R 22 R 32 R 42 R 52 R 62 R 72 R 82 R 92 Selected from benzene rings, naphthalene rings, biphenyl rings, and carbazole rings that are substituted with D or substituted with halogen atoms.
3. The method for synthesizing a deuterated carbazole compound according to claim 1, characterized in that... The deuterated reagent is a deuterated benzene compound selected from deuterated benzene, deuterated toluene, deuterated xylene, deuterated trimethylbenzene, or deuterated chlorobenzene.
4. The method for synthesizing a deuterated carbazole compound according to claim 1, characterized in that... The catalyst is an amine compound selected from EDTA, propylenediamine, 1,2-diaminocyclohexane, or hydroxylamine hydrochloride.
5. The method for synthesizing a deuterated carbazole compound according to claim 1, characterized in that... The molar ratio of the catalyst to the carbazole raw material is 0.005:1-0.1:
1.
6. The method for synthesizing a deuterated carbazole compound according to claim 5, characterized in that... The molar ratio of the catalyst to the carbazole raw material is 0.01:1 to 0.05:
1.
7. The method for synthesizing a deuterated carbazole compound according to claim 1, characterized in that... The acid is selected from sulfuric acid, trifluoromethanesulfonic acid, or methanesulfonic acid.
8. The method for synthesizing a deuterated carbazole compound according to claim 1, characterized in that... The carbazole raw materials are selected from the following compounds: 、 、 、 、 、 R1 is selected from H, and C1-C 12 C6-C40 aryl groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups; or aryl groups substituted with C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups 40 Any one of the heteroaryl groups; R2 is selected from H, and C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any of the heteroaryl groups.
9. The method for synthesizing a deuterated carbazole compound according to claim 1, characterized in that... The deuterated carbazole compounds are selected from the following compounds: 、 、 、 、 、 Where R 12 Selected from H, substituted by D, or substituted by C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any one of the heteroaryl groups; Where R 22 Selected from those replaced by D or C1-C 12 C6-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Aryl; or C1-C 12 C3-C groups substituted with alkyl, carbonyl, hydroxyl, alkoxy, halogen, amide, amino, or trifluoromethanesulfonate groups. 40 Any of the heteroaryl groups.